Synthesis and Application of Fiber Reactive
Dyes and Evaluation
ofTheir Fastness
Properties on Cotton Fiber
Th€sis subnitted
for
The fullillm€nt ot the degree
of
DOCTOR OF PHILOSOPHY
By
SITARA RASHII)
Department ofApplied Chemistry Utriversity of
Kanchi
2012
Dedicdbn
To My
Family
with
Affection, Apprecfurtim & Respect
CERTIFICATE
It is certifi€d that lhe dissenation entitled, "Svnthesis and Application of
fiber R€acri\e Dyes and Evaluarion of Their
Fastness Propenies on
Conon Fibei' submitted to the Board of Advanc€d Studi€s and R€sarch'
University of Karachi, by Silam Rashid satisfi€s the r€quirement for lhe
award of Degree of Doctor of Philosophy.
/"/
Ali
Dr. Syed Ishrrl
Dr. Mehdi
Htis.r Krzmi
Chainnan
Res€arch Sup€rvisor
Depanment of Applied Chemistry Departmed of APPlied Chemistry
Univels;ly ofKarach;
University of Karachi
Karachi, Pakislan.
Karachi, Pakislan-
Prot Dr. Nhrlid M. Klr8&
s r. x r.
R€searcb Co'Sup€Nisor
H.E.J. Res€arch Institule of Chemistry
lntemational Center for Ch€mical and Biological scienc€s
Univelsity ofKarachi
Kamchi, Pakislan.
..- ..- .
3,1
ca.td
3.2
Dyeing Procedure...........................,,..,,...,,,..,....-...,.
3,3
DdmidtionofcolorStragthofDy€in8Solulion.,........-,...,...
3.4
Dr€ Ex!!us:rion-...........-....-,,,.........,...-.........,. .........
Infomado.-.....-.................................-....-.................
,...
.. - .- .. .
.Dy€ Fixation ......-....,.,,,,..,,,..,,,,,-.,,..,,..........,,,,.,,....,............,,. ....... ..- .
... .. ..-..... ..-
83
,.83
87
-8?
89
.l
8
Ud.mi.dlirr'utlrVr:r"
Anlinnr.,bral
A.n.r)...
....
....
I08
109
ACKNOWLEDGMENTS
I wodd lik to exp!63 ny graliiud€ lo all those tho Srve n€ lh. posibilily lo
onpl.r. |}ii th6is. I wt to rhat ih€ D.plrtndt of Applicd Chmist y, Univ6ity
ofKd.chi md to hy suprisor Pet Dr, Sy.d hhnl Ali for giving mc adnisiod to
@@oe this lhsiq to do th. nesary rGe.rcb *orl dd to uc depdtn€olrl
I
nlilituoE to thlDl with d..! inddt€d to ny @supdvisr
Pbi Dr, Khalid M, Kbm who gave ne opponunity for @llaboralion work viih
H. E. ,1. Rs@h lBritute of Chdistry,Int rnational Cmt* for Ch.micd ed
Biologic.l Scid6, Univ6ity of Kdachi ed 6@umged Dc all th. tine ro 80
facilitiB.
I
d
hlve
dso thanttul to Madan Rahid.
dd s@@Cddi
hclp€d n€ in
dl th.
rdd
wh6e h.lp, slimdrlha sSeetio$
tin ofEerch 6d for niting ofhis
th6is.
Keni ChliAmon of Dcpaftnot of
Applied Ch@isty, Univ6i9 of KEE hi for ![ th.i. hGlp, swpon, interGt dd
ralulblc hinls. I m ale rhultul b Dr. Bilal Hat@, Meaga Appli@tion
I
also
wet to
lhank io Dr- Mehdi
H4@
Dflelopn€nl in Claier Patiste Ltd. Mr. Mohmad
M6 O@f
Altu,
P. S. O. of
Tdtile Divisio!
K@chi Pakiskn for labontory t61s.
Di
Shoaib
!r
Alm
PCSIR
aif,
Alm€d, P, S. O,
&
Llto6tori6 Conplcx
Principl€ of S. M. A. Rizvi
Tqtile lulitule for providins dy€ins facilili6. MB. Mo62zam Qds Nlqvi,
Diretor Tel'dclt at Fdid Alncd V.sda & Co. X@c,bi, P3listd fo. f.sttr* i6!
md old meffid. D.. ZaId-tJl E.q Qdmi fm rrovidina f.cilitiB for QSAR
snldies in Dr. P&jwei c6to for MoleulE Mcdicift & Drug R6eh,
Iridltion4l Cdter for Cbdicd &il BioloSicrl Scid6, Univdity of K@hi,
I d d€clly oblised lo my fmily for lovo, pnyft ed E al help in difficult dmB.
Esldidly, I wodd lit€ to girc hy sIeial tharLs to my huband wboe p.liot,
sulpon ed Iorc 6.bl.d he lo @6pletc thk wo*. I m griefirl ro oy lidr for
pmying s lol
fd @mpl.tion oflhis
work.
BIOCRAPIIY
w.t bdi itr K.t clti. P*iste. shc D$cd hct ss.C, tDn F zlu
Rchne S€coddary sdt@l .nd H. s. c- ion Govomd Karli Co[e8. fd
Wobo. Sh. got hs Hotur's d Ma3ta's d.8c Aom Deahot of chmktrv'
Sitdn RNhid
Mmlgcr ?inting & Qudny conLol h Al'Abid Silk Milb ltd
joincd Nalslbddi Indshi6 Pvt. t l4T€chti.al Diretor Afta fik sh. ercd a.
visiiinS fiolty .t S. M. A Riai Tqtil. hsritut€. Did . PdtnEsbip in Pro6sing tt
Sh€
qo*ed
s
Hilal DyonS P!t. Lld.
Ale wdlcd 6
a
prcc€lsi.S h..d in Esstd
Tqtjl. PrI
Ltd
Fdnll.d thc oppoduity giva by N. E, D. Utlvdsitv of Engjn@in8 & T€clnoloev
K@dri s ! vi3iting l*t@. She got qtrcll.d tu M. PhiV PhD PFg@ in
D@drridi of Appli€d chdist y UniGitv of K.t!.!i &d tw{Bfilv omPlcLd
II
Lbt of Trbl€i for Chrp&r Ore
T}liclt
Composition of Prw Cotion ....-.....--....-.,,....,,...............-.......-..........-,,..
l0
6s Color in O.Cadc Dy6.....--...,.,,,...,,... i 5
.......-..,........,. 16
Dys Cat.goria,,....,,,........,-......
W.v.lmgtn of Lieht Aberltion
Diff@t
Stages
of Dyeing
for cotlon ,..,,,...,,...,,...-......,.....,,,,...,,................. .,, 22
P@tageDstnbutionotchmic.lCl6esinRac,tircDttltuc5610r. .. 26
Iopo.lot R@clire D'€ S,sten with Tt?icd Btud Nrs. .-...... ...-..- .. 30
c.m@ial Rodivc DFs wilh lteir Bdd Nd6
..--
,...,....-.....-....,..-.....
RorgdizdionofcoloMiMdufelwInd6try..........-...,..-
. .
. 31
......
32
Lbt ofTrbl€s for Cbpter Two
Amnatic Anin.Uscd in Synlhdh
Didin€
ofRqciiveDyd. .,,,.. .. , ,....52
Bridgjng C@po.ats for lhc
Slnrh6t ofrE MCT
Dlts ... .
55
tmdaMd,AberbdetdMoldtbsrylittyof Svlth6i2€dDv6. .. . 62
Baic Inio@ation of SFth€iz.d Dy.''.--'--''..----'---'..''---''..'-''---''..' 63
PuiiyDah wi0rof MainP€akAr@wise ... . --..--'.,..'---_-_-- 70
Llst of Tsbtes for ChiPter Thr€€
Toblel: St€pbysi@ Dtling
.
P
Tabb2: Sp€fophotm.tic valu6 in D65. l0D.8 Obs.fl4.
T!ble3: tmd! Md. with %
---''-_-'..'-_ 84
.... ,. ...- - "
" 86
Exha$tio
- -
.. .. ....
Tabl€-5 | R6ults of Vdiou Fdlrlss PoFni.s of Dya ... . ..- ,. ... - "
"
Tsble6: Presot Red Rdctivc Dy€ StrucM with lh. Abetltivity ..
Tablc4r l-Md. of Fabdc with P@n1 rixsion
...
TabteT: Actusl dd Predicted Absorytivity of R€d
Toilila stdTgl
Sds...-.,,.-.....
--
R4ive DF
wilh Rdidual
"
-
--
88
89
"93
__ 96
of
-- -"
98
Ill
ListofTrbles for Chrptcr Four
Tablcl: Statistical R6ulb for Rcd Ra.livc Dtls Exr.ci€d by Comfs Analrsis., l2r
activitlc@ Posidve Bacldia)..'-'.-'-.'-.............. 125
Table3 | lnvito Antib.clgial activity (Grs Ncgalivc Bacha)....-.........-....... .... 126
T.ble 4:Invitro tutitunsl aclivity (Zonc of idribition in m)...........................-...127
Tabl€-2: Iwiho Andbactdial
rv
Llst of Figures of Ch.pter Two
ChMErogM of 5..._............_--.._'..-_.-'..-'.--.,........._..,,,..........
04
Fi8uF2: HPra ChFDalogram of5b........................'-__,.'-.-...................................
65
!i8@t:
HPLC
Fig@3: HPL ChmatogrlD
Figlc4:
HPLC
of5..,,.._...._.......__......,,,,._...............,....,,,..____......,,,........6j
chrmrrogrm of5d......_.........''...'-,.*..'...'-............................._..... 66
Fig@5: HPI,C ChDmatosrrs
otSf..._...._......__.......,,,.............._.,,......,,........._.,,,,......_... 66
HPlr Chromarogian of5g................._............................................................ 67
Fig@7:HPtCChmlrogmof5!.....__.....,.,,..____..-''...'.,--_. .__...-'---''.__67
Fisur€ 6:
Figucs; HPLC Chrcmtosm of 5t................_.._'..-'--_-'-................................... 68
Figuc9: HPra ChDbatorm ofSj .................................................__....__......_....._....__.. 68
Iis@10: Hlrc Clrmalo8lm of !k.....................-.....-'-.._'-''.._,.._...................
6e
FigFl
||
FigFl2r
HPL Chlmllogtu
HPI.C Clromarognn of 5n ......,......-'-__-_..'--_............................_....
?o
Liit
Figucl:
of St......._......--'.....'---..---,''.........,,....._.....,,,........ 69
of Figure3
St€p by S&p Dycing
ofchrpt r Thee
prc
_..,,..,,...._,,,,.,,.......... 84
FiguF2: Siruclurd Alieff|cnr ofAltR€d Racrivc DF by rh.
Dlllbe Atitmat
Mcrhod Usi.g iL€ Most Activ€ Cmp@nd 6t B T€mptate.
......,,,,,........,,,,,._.....,,,,.,,..._., 95
List ofl.tgur6 ofchapter Four
Fig@r: (r Dd
b)....................
...........--.....__...............
r23
Lfut of ..hcmc! ofchrpter Two
Schdal
..................................
......_.............................. 50
Schde2r Syrth6isofCouplingCdpondcl.........................._... .........'.-'.---..5l
schd.-3: Di@tizltio! ofArot!!d. Ani!. (.-t................................................._....... 5t
scbd|c4: DF Fomrlid Re.tio! ( a."af) ..._......................................._...................... 53
Li{ ofr.h.[€ ofch.pter Forr
Scbdcl: Wo* Flw SdaF
fo. CoMFr{ Mod.|ing.........._....._...._-.....,,....,,...,..._...._. 120
JuITTMATV
For @loaiion purpos
nw d,6 @
dtumds of icw fibric,
!dm6
ed
co.rinuouly beine da€top.d io m..r rhe
in drlins &d printing equipn€lr,
Th€
wilh envirermdq wolkqs. md
'Ite nost
rffii
rq
idp.ci of iheF
lMr
iepl'.ddts
cm be
on th.
ls*scd
hy
rchmlosy,
e e.i.rcd
ro ov€rcon. drc sqioN @vibmmral @nefu wlicb
distila dt6.
!s
tqlit.
wirh
s.cior in rctation
onpding thm with similr
tehiological oni.ibution io icxtil6 is ih€ dwelopmdi of @ctive
dy6. Racriv. dt6
e
subst61c. Usu.lly bondina
@lo.€d
cooFud. whi.[ fom @rd@r
occ6 betv@
-A, -C
bonds with
d -t .ton ofde dt! &d O,
,N, -S
olon ofthe substr e, Rdctive Azo dtrs conprb. of8o % ofallr€lctiv. dye,In ow
F€@l
study we have
The dqivaliv€s
of
ef€.t of dimiDc
@llulose
exdi!€d
!w
groups of r€acrive reds of procion H-E q?e.
l-amino,8,hydrexy naphthalde 3, 6{isubhonic 6cid md the
degq of dyc dnaudor snd dt! bondiig wirh
fib€6. Thc lppli@tion ed fst!6 t6ts 6ied our of rh6. dy6 @
bridge on the
Raclivo dFt wcl! pr.p&€d Aom cj@uc cdo.ide
(r-hino, S.hldbry
mrhthalaq 3-6{isulphonic rcid) by prfomins @ndos*ion, diaarizstio4
activalion ed olpline r€acrion. Tle g€idat sttuctuat fom a is giv6 below:
and H-acid
/cl cl\
IK
NsOrS
FN
\'*5"d&1"-'
- sorNa
N3OrS
'sorNa
Alr-(monocl oreitiuinc R€lctive dye )
Wlqe Ar represdis six ditrnmi arcmatic amin6 while DA is thfte sl€dcd
di@inobridging moieti6, with diflddlt @mbiBtios oflr ed DA, tbinm trfl
d,€ @ srrih€siz€d, Then lpllic{lion o! coti@ falric is don€ by <rluust mdnod
with
dtroll.d
lw€linA !g@1,
which
infl@e
lddidon of s6l! rnd sod! to hdc
a
rhe @lor stldy
oo
cuhs.
@ b.
.ll'
Ba
of
wiih addiri@ ofdy olhd .hdical
dyeing wittDur artditi@
vIl
Th. mlorincttic proFnies
and
f6t
s
of ti$e d!€: n.smd- Tbc influcnc oI
dimine bddg. joinine two clulDoplor. systetus
from dF dye baih
and
ws qdincd.
The prepar€d
d
tlE dcg@ of dle
dy6 exbibirr vc4,
good dy.
c$rution
tro}!r!€s
whd epplied to the Mtcrial spsidly ellulosic, plovid. !m!s rcd to blDis!-
dyei4hlvins g@d tuh6 FoFni.s ad they vft.ls chra.teiiz€d by tid
wala elulility du. to 0!e pr.soc of n&y sdls foming goups. This nak6 it
rcd
a
po$ible to clrry out dy€ing
pm*s with
d4r66
ont€ri in rlE dyc efl@rs Th. tyle of dihine
dd
@.rgy @sr
$ a b'ids.
dyc
a low liquor ralio euch
which joirs tvo chroboplor€ sysrfts
da$
15, whictr
uld
sisDifi@t illluoce oo the
a
dyc rfllnily to ceuulose 6bm. 4,4Urs-disminoslilbqe 22,-disubh@ic acid, l;3-
phay'oe dimin€, l-4 Phdyld. itiMinc
applied to c.Uul6e
bd.vior
diffue
G
bridg. which
is
ued
fibs rc pnctiqtly @olbed
qMhtative tnomr, It
du€ to lhe
ft
d..llot
foud
q
wilh
bddcins slou!.
thd by.6rrl.!r
ne dy6
bonit in
inq@s
ircMs ihe dye.$njly to.elulosc fib6. Th.i. sbbility
thal the
in wsIq dlc lo
d€gr* ofdy€ bondinS with
inccs.d
nuld
the fiber
of SO, gD!F, whjch in
tt!.
6ily
in lh€ fib6 to giE bertd nigRtion e.t tq.lir& O@d buitd-lp,
€xbauslion ed fixation s. fouod b6t for dycirg eldoric fibs.
The @ctivity of dys with rhe elutoe fbs dep.!d! uton the pbcioch@icd
pop€nie $at e ruled by paniodd fqruG of fte mot@b The r.cenr @n@p!
called lh€ lisedj€c€flor @ncelt hs bed inrldu@d which h th€ bindiry panm of
thc
t@fv.
dr
Nirh cellulo* fibd.
r. $c
1bc dim@ioDl
r-bnique qls 0pplied io
pre$nt sMy, the
qudtitzrive stiucnr lropcry ntsdoBtip (3D_QspR)
study the ..d r.3ctire dyd inidacliom w h th. @llulos€ by the Conpdative
Molddd Ficld halrsi, (CoMFA) aellod. This l€chliquc w6 su*srtuly ulitize<t
to tul€st a sladflst Eodcl. Thc pr.did.d hodet Imlid* qui& $tisfa.tory
sbristical
tslts
&d
i!
th. tight of th€s, ii pes
hnlq aeined. Iunlmore, lhc
g!.!hjcd conclBiou i.., co ou baps suppon !! to @mpr€hod the rfom patrm
od to di.lstc tbe s1nrciual.hdS6 eith cp4t io rhc lb$rptivity. Additiorall
*ler.d bod€l hs por.rrial b slpon in udasladilg th6 ch&.cr6isti6 of
|]r€ erta!.l tqsi !e1, This apprcach my po$ibly b€ telptul lo 6teDds. n€w
sctiv€
t!€ filal
dy6 with isprcved rtrniry
and
Thjs pa!6 pr.s6rs-q@ritlrirc
selativity for liie euutos fibd.
stru<rlF*rivi9
rElatiolsbip (eSAR) EFdels for
.
sdiq of 26 ,ie(nolochlorchi@ine) dy.! for @llulos. fiba by cooldativ.
vul
nolecular field araljais. 'Ihe clc.imnic and stfucnrdl plopcniB ofthde drB
wft
cdsld€d Fir.tion cflcidcy is @ roled by tne Eost intoi&t hctor, which is th.
"fibd shape f.ctof &d tlE study show rhrr noF plell srdctuG idd to luvc
highd r{tnity for lLc c.llDiosic
Eb6
4-4)ti
il- 4s,t JL.lJ,z tL-n-b-.- 2tr: 1L,-.5 ots
+- *r+ trr4t!rtr*.rr g,tir,.rL:l d..-G J $_lrJz!.+JJ,r d
jt t,*L z:, lt- J rft--+,-,r',rrrr,-(j,!,+.-,f+;r.,z,J?
r\,'t d'.t jt,-t!Fr 2.
* J!tt-€ J-1"fr,J,rr, /5 us
11-z!.$)o)+j,S c) Jsr,tFlJ *!ir r|Jr:.' $-elJ
or
"-t
.r,*
t'
Jsn,ne-, ;-o;+,+ J+*
-4l<-c'qJS
Ju,rr.+,q
$'-
.].-+t,t.:L
I e--,.t rs -tt - o=l,rJ-tr.n, J-r!-4.
o.N-, 4tvr-,rrr+r p rra,c,
J !3rrt rr! F. olqr, J-.(r
Ll,r'&j^. e-dirJ J-Li. rLr z, s{ J*<l!.C!q ol+}J.+rs
i' J-L,.tP.dbr $E tp! 2 .r .F lLJIj ;c-2.tr+q S,qzo
jfr-r.t J4Lr s-Jrrrt+q -rJur, _q xj+ t:i lg E zl.&,
^
jN,
)-r)L&)dL
lt elrrJJsojr.t gigrr Lt4r.trtt J"!n;i
I
zi, rL:.' r--rj s*ri rr sDlrzt uF, oL |' f.rr.nlq sJ.nrtJ!,
sjirlj+-^,rri-l- | )!qrH ,t.Llrrt Jrli-y'D^r J-r!
:-tt t jts,**'l'2+ z::f JL+trt(l-rdrir* s.jl! r r,dl$4r
r'u,r LtJ"ZelJ G+ J- rr.!Jri sl.*.drEorabn
ulJ*ud
-2" Lt rr
u- &i .r.i.3 s-Jr tt
2trit
NaOrS
,iq|mocl
oretrieift Ro.tiy.
dyc )
x
dramane-
!-t.5ol)A
,ltulrl,lil--
!dj;-+_i^r JL+
r!j- SD\'ur j-J:6 eit FL, Jbrds u n'oa{ies
ltst LJJ
J.arr- rt Jr elh,t rr r zil j,3ts-o:::
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,t a eL.'-tt Aa z.- r,L)I-r" oL Jr tt {rJ(llr,jLl.r :,+ S ,t^'-+.:l
h.<-n juir;rr€lia.it-r Lr:St gVS z,-*
91 ,*.Jt!- J.nJ
,;z-
-.'t-
-4
t*r-- sJ .r,t-.-4.n,
2\t zj-+; lr,tLt 4--,5
eU J &-,;J
';!J!l"' J"r-r J.irz!t.,-i+r tJ -r,iJ J+ #u t u.j1j
u+.r J (Jl&,2,Jlr,JzJ,t
1(r-,r dtL 2$t't 2\r;i ))-)-,L-A\,rJ .l-rl Lt-L-r-,.r
uf ,ro.f 2\: z4,A*;-;, 21J-v.*,.4,.'\t! ftttS,C,--u,rl!
z-.itc;^- u\s sp s/t- J.r{ &l*:i}'r |!.;!z-.:-r J,-"r
.t-* a. qr Jrjr tt e*rai J ('K,4-1:s jt!+i-J C-{
,J en
J;j
.e
J s*rr J
drni ol,i -
I
j.!, .;l, J.n,rl -++J .:.ulF
ajlt^, )-t,J* 4 \rt)r ,t rr-u,7r:f :, 6 r or J./,r \J:B Jrr 2,r
'., (FtL.r:JLf lrnf bis-r'.tzi Cf ,."r- -V Z+\un,tr'l\ z! ot,n
JL*-l&
4-L+2,
uf
.-,J- *ljJ
|.l-]!4rrl- jB- r
o!r,+ uir .nr Jr2r+ lstJL.!!, rFJ jr}*Lf qt J\et zs {s
.tn e.!r.l L," rF.r-f.c.!. z:" ZJ G,\Jr. t)t t tr.i--!,y'"!tz)itu- 2r+ 4tr 4"t z.- +rJ.!.ra.>J SIrr Ar €l.- S *l
It stl3 J-rr-!r,:.,.. |J!rr2 !J+r_r.t.iL:r u? -_+; J rr*,1t ,rr1,
2*f tt^ "u;u z- jLl rt-.s a.,.' "f "f '# g! vfsG .rGJ .ll|*) .!, !t{, jrJt- -.tr zjJ -}J rt *r,!j-r )Jr (lrir J.E lt+rrrr!'r
J
J*,-Jo_rJ.,JLl (il3
sr,L! r- ' '|:;n CjBlrlljj-r.
J -tL+ rrr Jr{ .F 'r-- .!rr(jJt+l{JJ,rrJL,drrtdrj, J-t :Jr-.i,$i-J,j-.-:{,j*lr:,
++-
o.r !r--"
rlrrru .=-.-,^
z- -. , J .,9iF
,t,\L,r. )\.. P Atf
J"G.rtbindins
C); z!
a,*
J6)u.Pt-i- J 1--t4i-t4t--
zaLrL-+Jlgard
Jtr-!
al )i .t\L- ;t CJ-1L-i.K) J-sz
/ li Gf i+
-.J.F "-F
J-.:6
p^en .8- S ih )j j+- lt.nr J-l-'
\i'!-l9,lJu, u-r & u..2tt- d:,*
CompaEtive Mole€ul Field
z.- G\,'tt
receptor corE€pt
Lf
!!,t
PA- duS
L.-l
glr-l-r J(3DASPR)
f
,ts ,:.-)N]€lysis{coMFA)
a,-
Jsleadtast
model
.rl+t+
+-tl lit
JLr-l
sr'.r,21f 6' r.+ 6 a 3v,..-r oL+Jl Jeu J !L F, -r+L:-- 6-.r JLr-l
,t -- {E s*it a* z! tLtl U.tLr .!-j- Lt.,.lu+,r,-:, J e. L.
':t
2t^--J 2j: '- y*:2,
z1J..Jt--2
rJ :in u.r,rLcontour
I rv"f 6t; '- o. 25 S; -d": - )\- I
otr-
o-.a-
,t:;ui
ef
J
.l:r++ LFL-
-* j^ J J-j jr,+ Jll-.!.-^;* ciil 6
,t*4 a z! a,4t )i-)--Lt t
- a F_,:.=+65,:* o-. u,+
26bis z-,t
+Vr
€1-
jer 3+.--- L{-r e-iu
J.rF, J-',- j J,-L li *l;rr
zf -)-r: J,L,irJJ;r'.- i,-+ -,t-- r? ltJ- rr
ir';,- u-rt' -
1.a-;i F\onochlorotriazine)
u4tt rl-tb 3;t- )5t g J uF, oL J r.t .JL--r ui u!-(osAR)
-!r ! ,Jrr
z- r! Jtfibs shape taciot , J.- it z.--- ,t J 'S,6 J E
-.tL Gc. nLi 4 z!,..J )j]*.t aE-\ nL + L-.r$-,tr,{\s JtsS
-a G|J-L;r ;:-t &)
cJ-r
d
,ur- / zJ
xlt
Chopter
I
General Considerdion
Chapter
Intoduction
Tqiilc
d
is
depend on
l:
to
General Consideration
T.rdla
iepodlrt
inregral p8n of
fi€ afrodability. 11a1e
fd millioN
of p69le Th€
ou daily lift ftm ou baic
adds ro
tmity
n€€d ro
lu!ry,
th. n tion's wealth tud provid6 s.ryic6
of teirile is to proted, provid. @nno'l hdvc
ecial meding md phy idpondt rele i. veious turctions in all indutn6, Th. main
p'rpo* of latile b clolhing *hich in hlm d@ed o! wioN faclos: clidtc md
wethq, f6hion, availabl€ iahnology, oltutol requnmds, the @oMy, gmde!
dd rge, in@De and mge of textilG aEihblc. A study of tdtile rh*foe uil6
clinalolog, chmislry, phFics, oeineaine. @onoii6 dd $ciology dd of eNe
Teriil€ is thd @mnodity for which €!.rybody is
mdsranding of tqtile nor only
ale dryelop lh€ ability
relet
for ptupa
to
h.iliilr6 d inrelligat
e uhm.t uq.
€valu.ti@ of slmdads but
disiinctish qu.lity in flbrie *ticlr in
us. Texlile indust y is ve.y nultifsios
wilh fibs pnrducrion of mtunl
6b6
Ample
s
tm (mle qitqi!
ro
it initi6l6 in aeri@lture
sh 6 @tton, jute, nd !d
olhd fibrcG
silloom, in mining of ni.frls md
neIab, in fo61ry of vood, in.ldiQl r€s.lrd 6d slrlh.lc pDducrioc. Th6
these fibes @ lrqt€d inlo
to make fabrics wilh th€ h.lp of diff@t proesd
'tmnrfling, IlE fab.i6 art tasfomed into lhc dd s
nmely w€vin& kninile rnd
stufis, which ofd sp@ific look ed p6fmee. Ili* clothi d a poducl g.t usd
in wio6 induFi'l applistiotrs, appet ed lone fmislins. Th* prcdu.tr with
tuultiplyins cf€c1s mfthsdhed in sto6 ed tho eld. All $ov. n@tion€d fields
@t grat @e opportuirid in rhd a t ldd who sde ilm r€quirc slcspopl€,
Nron6, mq(nedis ndg6, snd oth6 pqeMd for the dalirg of t xtile
good!, Wrile the produm of tb6. loducls ne.d but6 fm fabnc. d6i8r!6,
tMa86 ftr productjoq s.Uds, .lc Th. neuhclu.d of t@ ard fabdc tr€.d
€xpdico@d pople, The industry which ptu@sed th€ tatile ed which d*ls with
tettilc clmic.ls 6!iB tiincd leMmel ir a Eious fid&. In drlditid to dl th*
plmts, in
{mins
of shee!, olhd eiDals, md
Chaph
fields, hdk€ting
1.2.r
&d
adv€rtising sFcialis$
t l: Cencral Coasid.mtion
de llso
r€quired
to !rcnoic re!.Ld
Xiltodcd B.clgroud
Sine
6ly
Stonc Age
ma
had struggl€d a tor wirb
.
w€t, @td
ed g6e.jty
lllrl@plive clinate. He usd io have foughi rufi linutoB with rhe help of eimd
stirs, tuB, md l*vs for @v€rirg whethd in th.L usl srate o, aftq .uttiq dd
w'ra $d. Atlr
fie
Sronc Age rwo
p.initire civiliatitu
m
bc
s.,
The
fBt
foo h vho live on rh€ m€ar of hur.d minah nucd s parrimtul (father
doniuted) fom of eciety ed .Drhd one n !g.i@tl!E pDdlc.d mlEieh.t
(morbe dminaled) society.
Unlilc
het6
Natual
fb6
pl&res, a 6ird rype of eonoDy rlDr of nmads ddse4 pho
wft not lsqt to hunt minals, but like to ttne thm. Itey spMd thbuehout from
Eat€m Asi. to Nonh@ Atica dd Cdaal Ewp€. Tney invmled
tdrs &d qrpcts.
and
6p4ially fton pldrs of best fib6 (fld, ju&, erc) providcd !t hitsl
slag. of ne, ! mlc.iat phich fom fabris ,ftd pllNi.g
e ldveed s|ag€ of
W@ving is tb. mosl
imporht dis@vdy attci naking of ym,hich in tuft requircd
for d.vclopodr ofncrhods ofotding ro rh. fibd and
falnc t3l.
Cohon wa problbly groM at MetriSarh alout 7000 yess
sgo. Actual pie3 of cloii
e@ foud alt{ched to ihe lid of a silvr vase dd sone coppq objecls
at
*Chwr:lmhtMo,
sr.Lt rbaDd.
E
ridg.t#cd{..ro (-d
n ri,'r"S
ddd.l&rd
Dlr.onry ofdr
Gloy'bS
o,H{ (&,i
$)
',q,
(6oES6100
re{o)
12,0m
t000
r,6 ry)
d.oftd ft' dlt h O. R.o& EDdE (rto{r2ooo
8.?Gdf-
.C.S|.do
H!r! lfr 6c r&. h 6. t!d!r!r
orfihi.
(sch.!t+D
Flc(aadd..r-b.l)-,'/
t!@
'rw
r!r. .ro,
Draldd
ro
6d|!
d soodr
-r.b
qe-ilhi|c-b
8.1-'t EFc
of f
ifi. Cqsdd,
Chaptet
1.2, Kbd!
l:
Generul Coksideration
offib..t
It i5
cilla spu (ttlisi.d)
y.n d
dh.tty cmprlls€d
into fabdc. And ps3ilg rhrougi mny stasca of civiliaiiod
this ficld b!! !un@u kin& of nb.r! (Sch.r;2). ftc bsic
inio
bowlcdge of which is d.!irau. io
ctse
dst
wiLh filnher
Fse$i!8
TE"!$TLE NEEXS
I
Schcb.-2 Kitds ofPibq
Chapter
r.2J
l:
Cenenl Consideruion
C.[rldi. Flb.E
c.llulGic nbe6 ac ilos. whicL @Bi$ of cettulo*, &o ,E
origitr. Coito! is rh€ @jor
$ue
of ellulo6. *hich h8
IMy
a: good db$!boc/, comfodable soft hdd, bE4hing pbpeny,
rration, prilts v.ll, n!.hjn. Bh.bl., dly cle&.ble, dEF,
dd s.w TIF biggst
culrivarioN of cotlon
@b
b€
foud
i! Cbin4 lldia, USA,
Ee).t, Elst m Eurcpc, Sudo ad p*isran
[5].
Coftod fiber grc*rb
hs fou
bioch€,nicd
dd clroloSical phs, t6l.
Seordrry Wdl
Ifi_.
Tlhk..bg
Etona.rio!
S.h.u6! DaF post A!rh6i!
h !he.
on. rhc lha|olic ,r!rh6h sraiis with @brg.Eat or let@lus
dd
fomdion of nerhyl sr.rificd p€ti!, I! p}!.
tro sr!rh6* of p€.riD, dwin 4d
xylogllcm slarts yith nuct@lus dimindion. Wl
le nerhyl-esLrined pe$n geLs
Chao@
l: GeEral Considerution
r! pha are cdlulc rydtdir n ttr siti d6qr h Kr ed ubrc. A{dc
8d ndi.d !o srtuiz. in It* b.l od b! fotrd hi8! Fqidr& dn ity.
l.3J Ply.i..l .an.a.rc
Th. rd @nm is digild.d A6 &. Anbic ligwe. Tt !! n tu F@u.ed s
quE, hro, qllm .ra Cocd 6t6 shid oh.ird A6 r pbrt i3 .d€gdiz€d a
cd ctud,
e[ul@. m@..[uLr, ad dlplc
Itrcr
A 6noo fbd coryrlB of
.
a Bnod
ctdicb,
fibcr
(lh@l).
ofc.do Pld
FiE, s[, leey
ea[, ed a hlm
(fir.c2). C.Urrlc p@.d.9. id cdo fiDd i! mDd 95%. Tb. rn of lte 5%
d.t6 tu waxca, sdd. GLdt!{|!, ed litog@u odq, *ii.h @ @ioly pbc.d
b l[. Fin ry *al 8rd 3d. i! t!. lun(i.
It5r-l
C!o6
S.dlnof [.]&r! Clitoo Fit
.
Chotlt?r
Conon
fibd hs mtur.l
I C
rorations calLd convolutiols
eQl Const.te tion
thrcud thc tull lenrth of lhc
tbs. Vho tu nb.B spun the ye, convolutions h€lp 10 intcd@k then strolgly.
'fte nmb€r of dvobiiois 'npcl inch is about 300 fd lons iibe$ and for shon fibds
rntxi,nu 200. Sccondary *dt also @hrris€s of librils ihd erc oigeircd 8Pi$lly
md inrcN i! direlion a! @nsi$.nt intcryals (FiguF3). The inv6. spilds bcienl
lhe @tton fib.r lo hlve bcn r clanicity
ed rwisl blt lbout
15-30% EEke n
qeld
in
rtrErldrlltotnE
Agrrc3 Re!q*
The LnSilr ollhe colton
libd giv€s
to
SPiDI
$c fib.r it!
ofcono! Fibd
lild.s od sb.ngth. Coltm fibeu
Phvtic.l sttucture of@tlon is divisible
in five nlin pans ia ld8ilL tyPicd patt!, convolulios' ftntus ed color' L'!s!t
in d€snption of cotton qu.lity, lhe longq the lei8th of
pla's th€ mosl inponmt
v&y in lensths fiom 1,4 inch !o 2
irchq ftc
Pan
dton fibd lh.
stlongq siU bc tic prcd@d yam t7l.
M.cm 3truciu.. ol @do!
A cotton fiber appcs in nicospic otb.Naion s tegoh fine 6b€i lts 1681h
v&i* Aon about 1.0 cn to 65 cD, codilionat upot lhc fit'r quditv laglh lo
bGldth dlio for bsn qlality of @tlon 6b.t
fo! tla shor&sl
ed c@F on Th. nlio
fibq srobe spu into
{hit
ym
vdis iod
is di@dv Plolortlonal
N0tur6l .olor for cotto!
to ninbL tar dependins on thc soil
aboul 6000t
b
'
to almosl 350: I
0E
asn*
for
Iib'B vdica in @lor tsn ofl-
ed climaL t8l
Chaptet 1: Genenl Cohsiderutio"
1.3.2
Ch.nicll St ucture
tE
of.[ pLd bri.dds *nib $. ccllulos Ftqtrge in @not
is 909/0 whil. 4F50% in vood. Tl| oton polymq is ! linca, 4lluloe polyma .td .
e orydic dreoud wilh i!. fomula (C6HoOrL a polyscchdidc compdsiig of a
liIE ch.in of . nMbd of bundrld ro abo* or Nond Eo rboMd Al--4) lintcd
of D-turhydbglEGpltep uitr (AG?u) t9l.
Ccflulo*
is
by 3l%
[
I
-o
HOH
,**
l,i-\r-
I/OH
lll-:l
LI
\
i\r /
L HoH
I
cH20E
rbJle-4 Ccuobioe Unit ofc€Uuld.
elobio* (llgrrE-{), rtic!
! FFll ui! ofihe pol}mr @sislinS of
moahous ud crystauile Fgjon (Fig!Gs). Il3 clystallirc ponion i! abo 65-?00/0
wbne dorylbB rSion is dout 3G35% [E, loj. rh@foE, t[. @oon ldr16 a
l1s
dind
is
*€ll odcntcd ed pqhcps
no
nlnhd
is
apan
ths
0.5
nn\ in rh. c.ysLllinc r€sioN. TIl€
ofm!oo.. is €stinli.d 6 d.g@
$dich is di@{y popqlion l to lh! !tog$ offibq.
polrbd lagth
in rcldion
ofpolymdization, D.
P-
'IlE OB groups at .ach .nd ot UE c.Uulo$ chah h!rc dissiBilu pctfo@&cc. Th.
c!bo!
onc (C-l) cnd hls rldudivc prepeni.s,
4) of.ndins stucose unil k non{nlEing in
dlhoud OlIgDup
Dtrc [ l].
0t
crbotr fou (C-
Chaptet
l:
General Corsderation
133 Ch.diql Prcp.rd6 ofcotto!
dviommt
in walq ed in conqrrat d
$lurios ofcen in &id$ elrs dd bM. Th. swelling cE6t is ulally ouibur€d ro
Io hich hmidity
@tton swclk, also
the eQtion of highly hydEt€d iof,s, Tbe noistuF absoDtim is
by cold or hol dilde
10
?-8%, It is atracked
@rqtzted &id elutioB. Hyd@ellulos @
prcduc€d d@
rcid hydmlysis. We.l .r!d @ld acids do noi aff@i it. Th. cdlulos fibqs show
good r€sislrne io alkdin€ $lutions, Only th@
@mpl€l.lt Oie exdple
h cuptuoniM
(s€hw€ilzd's G.8ot) coppq
wo
onpld6-
e
f.w solvors lbfi
hrdmxide
ud
dislv.
@llon
cupnelhylo€dimine
Ir lhows good silbility rosdtls stoigly
ldrpennE id the sbme ofoxygd. Alihough il is
very stuitive towards nindd ei.Ls which act 6 oialyst in th€ hydroltsh of th€
bonds bct*h gl@s hits wtich EUlb in dcpolFriation.
alkalinc elutions
!t hi€h
Degldaiion oI 6hon is 8ctrqdly rEaeditcd to hdroltsis,
ttps
ox .tior
or bolL Two
of oxy-*Uulose @ry due to oxidation of cellulose dep@diry on 0le situatio.,
in which rh€ orid.rion
tat6 pl@
021. Alttlugh, cotto celluloa is 3 polyaldhol
but srrons hydroscn bondins do not
polynq Doldl€s, wm in the
bMk
6ily
w!td.
b.tvea hrdroxyl
ln @tity wlra do* not
.ryslallin.. @mplct struclw but p.ncbt€ inro th€ 6bols
Ae!obll[:l&!
I
ercups
c.."r".
ad
oradj@r
ald
in
th€
morphous rgions
r'* | **qt
oo
of
Chaptet
As wacl
tum
ndc
hydssd
bonds wilh
irqt!.s tE fibs.E68lh
hydDxyl
{
als
greupG
ofditr Etrl
G6 pritury OH
bonding
is
te
Ceherul Cowiderolion
elluloe hldrexyl
031. This fa.t is cxpbined by thc
poliMitics, atG2
prcst
l:
wbich
ereups, which in
p!!g@
&d C-3 s!.ordlty O}fis
foffi itrrou
of
thE
PE$ vnik
i!1d &d iatra-moleuhd hydregc!
Il4l.
r3.4 PrcD.ntio! of Cotto!
Ilaw conon is
mpo$d ofadditiolal
pulFs. of icxlile
prBing lhe
@mporols
(I'blcl)
@npon nls ml|n
t!. e
BeB. Th. sequ@. of diff@lt
T.blFl
TyDic5i Cooposition of
be
!o Srow
s
Plml bul for
Emord to ndc it ur.tul for
lto.ac (fk!F6)
ro pEpde @fotr is
Rr* Coion
86.E
0.7
t.0
0.5
1,2
l-0
6.8
2,0
ln $!e prFrr..tncnt
pbes
@usic *tlich tuncnoB
s
of corbn dalctials, th.y !@ boilcd with elutions of
lo dulsiry
rqca wlil. fds dd
PtotliDr gct hldoD%'
dd etubiliz. nincnl sslls. NoH.Iolosic clibohtdnt s of 163 nole' a Fislt
@ de Senilg mv.d. Aldosi 7% wight lN occEcd duils $is t dtrnr ftoE
colton. Ble.chitrs t!@ves the natudl
is
kloM
6
souirs and bl.dhine
y.llowth color of @dod Alka,li boilins ehich
coolirually inclrd6
$nc
desrcc of ccllulos
l0
Chatlter
oridatioD, nducing
l:
Generul Cahsidention
th! svmgc hol@ule *.ighr oI0E polpc.
0ll.
Anothd
isportalt p@css ir cofton prcpdntion b M@riation,
lmess h which eslic solulion i! .pplied uda te6ion, ut l
most of thc NaOH had b.d wdhed olt atq th€ rr€.llnol no sbdnkagc @urnd
dd thc nb.6 devdopcd a! ailnclivc lNr.r. Duing th. prd6s, .rte!9tio! of NdOH
M.Mrialion
by
i!..onotr
ercup€ ard
is the
fibcrs clrs.s acidic dksociation of a sisnificdl nMbcr of hvdrcxvl
eith the llelp of X-ny difiirclion tectflquc
qyslalline sfirclue appclr [151. In
lo*
i1
b fobd our ch4ge in
@nc.nttdi@ of .ll@li
mud
5%, the
atuctlt ofcotron ed s
th. concdhalion of NaOH inc..!res, the nmbq of ML. bol6ul6 pd nola'n' of
akdi cdwd for th€ fodation ofrclaliv.ly stulld hvdrat6. Thk Eduction in 1r
di@&t of hydnicd dk li 6ctc it capable to !.letrate iBide lh. sEehlrc i'
dimeilr ofhydFlcd ions s.
very big to peictrate inio thc
dolphoB ando. crys|.llirc Pqn of{lc c.tton fibd ll6l.
A @Nidcoblc pFssw dc!€lops {ilhin the lib.u !s wter k
dd
lbsorb€d bv
diftsio'
ihe fibcr swells, c.usitrg to los. rhc ch@d.isric convolutions' Ancr Enoval
of
fihq adopb a m@h rcud't cos{'ction dd
@mn
hisher l6t r. Nowadlys m@d4tod k also pELdlh bdl$ merced&d
a!6orb hiShd Pcrc€nlagc of dvca .d eira3 dcp sludls of dveing Whs lhc
po6sr FquiB impro@nt in dy. sbititv onlv with m lsGI lh6 sni-
the alkali by wshDs proce$, Lhe
ne@dzalion ot clutisiation
qih
15%
..utic
so.ta is
dicd
out [17]'
A
I
+-l
Fi!lrhi!g
rEurc{
Conob P'oc.sing ScqE
cs
lt
Chapter 1: Geneftl Considerution
t.3.5 Tte
T.iilo Cbdn
consh6 of variou stagcs to piodu. tl€ .nd uq lextiL pbdet olguF7}
Convcnno lly atoud trc
b.foE lhc Foc.dw b.gins qith fo@t! of th.
tdAer Eodrct of scent &3isDs, cloilts, sh!d6 od th.l tuishee.
It
rld
FisrF? fti6.
31.!6
ir
t
TcniL Chain ll8l
t2
Chaprer
1.4
l:
Aenerul Contideratian
Dy.iry
l.4J D.fililion
!
FoccdN to male ey ma&rial @loEd wirh dye s,lich hs lo be
ltllll@nl io $m deec. Irs p€fr!|rmy @lq it of highd valE itld shiniDg
091. 'ft. drr ch@brized as, it should be @nalic oBeic cdpomd which
Dyeing is
posss color wirh .ffiniry iowrd! th. sub.ltr& @ ltich
n
hE io b. applicd [20].
1.42 Color
Cold i! csrial ro n &e nl|tm qiltcM nN cbmins, iddiryins and
feinaljrS oo th. Earlh. It h s$ocial€d qih cmri@s *ens el.bnrionr .nd
w* Eqrd|!|M! in ou dlily lift.
fte impoi.@ of colc k .l$ .nlrlcad by oloDrrio. of Ere in vhich v. jrds.
tE quality of food d siih 6c fishBs of m..t, vcg.tlbl6 ad frlit by the
Mghtn $ of lh.n ob. while ddlnN d.!qib6 r,t aged nal. ial. Alllowh th.
p'4o* of @ld ir mi y d.contile blrl ir is.le urilte lo @@uiq& 6s.ii.l
infomtio4 qaDple of thd.rc €l@t i.al crbl6 @dd with dif.mt 6l0ls and
G4 relN ald gta td6c liCts t 2ll.
Color ce b. <lefh.d i! tbt tuin l@r i. bE, r.lunrio {d valc or lightK
(HSV or HSL) (Fig!ft{) 1221. 'Irt. dc
mb
lechniqes
i4
c
ilere io giv. @lor
10
dy
@ is tttough s|ining
wh€E .olor *irr Lqkmily, nMb.r tm i!
pigDotdion in ihis olor did @ly al tbc
lubslrdc
3uhe
nmbcr
of the ndcrial by
qd!16 of
this is,
m.u
of
nx*iv.
rt lc 0E fiid
phenod€i, is dy.bg yhdE the color
FI'|I,I|*Y of loh, nEdim or
valw
1231.
Cer
higbd
FigrbS
HSV Cylirder
l3
Chapter 1: Aenenl Co6idention
color is d@ io
lidi
ehich hls a b@d sDecEun of
'ldi.tioN
in which tbe
isiblc
sp@tM @Bisb ot radialiod h.vi.g ww.lqglh! b€tr€er q4roxinalely 35F780
m (ns!Fe)
124251.
wsv.l.nqtn
ntlc9
r.4.3
n
nlnom.t€f s
visibl.
Sp€fln
Lilil
A lighl
m
b. chaterized by
!|t.a
of mrey,
wrclcngth ad tlqeey dd il @nmdy
mtu@ in mon€l€r (M). Ttu rclationship of
tl*s. t€tu b lhlr nlqency is diF{y Foponionat
lo 6dgj' &d lhcy e irvq!.ly preponio.al ro
Mrcl.ngth.
eMple 6
lt m b.
explain with 1h.
Irlp of
mrdogth (40G
a20 M) h6s bighd 6€rs' t26i. tlqiis's di.strD
(FlguFlo) illusiraring the conpositiu of nix.d
hrc p.rceptioN fim ihe 6iquc hB l@t d o!
violct colo. at slFrtq
rtlFloHcritr8l Diagm
r.a.{ Bui! fo. Color h Dy€
oM olou unlike lh. olhq org$ic cmpou& for th€ [rst reaon 0Dt dEy
.berb lighr h thc visible ds. (3EG750 M), *cod t thrr thcy have at minimm
m @lou-bding group ttum a chsmolhoE, third tlsn is |}n iLy nusr h.w
a co.jugated amgd€4 itr siich doubl. dd sinsle bonds e in alt€matins
Dy€s
Chaptet
l:
CeneEl Consideration
s 3Lbilizing fo@ in oteeic
coopotln&. EM, if . sin8lc fatule is missiag filn lh. molq.dd fmtion th€
colow will bi vsish.d. ID mdst of the dyca au@hrom€s de Ps.!t *iih
is {rat Uey show
r.ena@ of eletoB, thrt behav.
oboxylic ecid tnd hvdrctvl ioB- Al$oud rh'F
thc sl*de of the
sreups e rcl cpoBible for 6lou bul tEir cxistcle o .hdee
d}! qbiL their min turciid is to inprcve lolubilitv [28]. Trbl€'2 sho\ts itt€
corcladon ofEbso$ed and visiblo Mvdcrstr tl3, 291
chmnophorc
..4
sultotric .cid,
TtblF2 Vsvelength ofliSltt AbsoFdon velss Color in orgsic Dv6
Light ,bmrb.d by
lh.E terld
400-440
4354E0
Blc
480490
R.d
490-500
500-560
560{'d
5EG595
Ble
595-505
Gr..n-Ble
605.?00
Rcd
l5
Chaprer
l.aj Clrtdlhrtio!
Dyq
@
b.
of
L
Cenerul Considerction
ltra
c{.todud
by fouowiog
M}! T.bL4
T.blFr Dy6 C{.sdi6
Non-Ioric, Cdionic
Dyc
.bilitt of fbcr
ed
An-ioaic
C.Udoliq Plot ia \v@L Poly6i.r dc
Aci4 Dinc! Dkp6., Rt
.ri!!, Bsic.ra
Ato, AathnCuim!., Stilb6.
oliEi!
R.4Cc4Bhl
lr.5 Dlr Cts|ncdlD! A.coritbg
th. t*o erin €t
8o.ica
ofcololilg
ao
rhdr
N.r.
n|ll.r.E dFi
dcfad i! th. bcgiDinS of rhi! chplc!
.nd piguErs.
ry6
c
wi6lt
5Llady
lddiridrt Fo!.ity s n ilbrtd b.
lolubl. d dis?cBd ir rh. iolEnr ofdFing which i! ulurlly !l!r.r in tc ca of
ltdila wlilc Digoor3 .r. th@ cokr coolo|ladr $tich @ mr lolubL in ed.r .!d
D.d .n dhBiE
r{i{li{y
n, gc! boud wi$
l! ft6 (ngur$I) [30,3|].
Chapter
r.4.5
CL$|fiqiioo olDy6
Dyca
ce
b€
d.goriz.d
l:
Generul Considerution
TrbLn,
by fotlowing mys
TrbleJ Dys Cakgodes
Noddq
c.rionia
ldA!;;fi
Allulosic.?mbia Wool,polyestck/a
,a.ci4 DiEcl, Dis!e$c, Rcr.dv.,
B;E;;
Ae, ADIbnquinoq Sdtb.E
odSiN
r.45 Dy. Ctalificrtion Acording to itei,
llrc two
Nlo6
din
cd.gon$ of@lorilg baflq e dFs ed prgn@ts. Drq
@ .tGady
delined iD the bcgiuing of ihis cbaptcr
with th. ld<tirion.l poperty ae ii should bc
elubl€ or disFG.d in rhe elvenr of dr€io8 which
is cutly wat r in the ce of
texlilc. Vhilc pigD.nB e I!0$ @lo!
on D@ds qtrich e lor solublc in w!r.. lrd
ne€d e adhesive auxiliary io get
bound wirh lI€ fibq (Figur._r l)
t30, 3ll.
l6
Chapter
DtglFU
L
Cenetul Considerctioh
Ctassitrcrdon ofDyc! Accudilg to ol.ir N.m.s
lb. id.lrific.tio! of dye TI|c Socidy of Dy.rs dr cotdtts joi ly
wirh
Aneicd tu$ciatioD of T.xtilc Ch.nilr ed Colori$ ns
devclopcd ingenios
3rstco fo. dNifiod@ of dFs Kroh s Coto.
h&x Nunbc6 (ct0. ft ct$if6
For
d/$
by dud sysiem. Cotor b.tex gcn ric
!a!E .Dd color i!(lcx coBriturion nubcls.
An NiSnd nnbc. dcfc 6. clcnic.t cbrs &d
rhc Sa.ric !n!6 id.Drig lle
ulage of.plli@tion. ror cxmd. ,Modrrr
bla.t l?, aa @ dy. aplricd as a
nod.nl rd No. | 7 i5 i! l[. tist typc. \'hilc turtq ooept.
a, cr t 5{t 0 is i! dE tin
of nonoazo dy$ (l l0oo- 19,999)
[33, 3a].
t7
Ch'ptcr
r.5
I
C! net al Coisiderutio,l
gilrotiql B.cksrluld
In e&ly slagB of civilialion,
tlr
fien suoundioSs in
rc@bluc. of mtrc which they obw. aioutrd th.m. It@foE ihe an of dycine is
st n€d with hrDe civilizatioD, b @l rhcr! is m aidencc fourl ttat e!.D or how
hllltN h!rc $aned b color lhcir dinab, qdls, vaporu, !d r[.it clorh! fq rh.
putlos of idcntitlcation or baautincrion [351. Bul it is sui. thar i.itially color is
peoplc u!.d lo ddotatc
|!rd
aon nnte a@idcnially by $b6nc @oking food a l hrnd got staircd vith
thar or by sinins o! ircn-rich roil or duing the lainats litc ahap gFzrd dlong *itd
shrubbeiy
th.ir
il€{.
g.1 chanse of color with Iiuits juic.. Ancied
!@
ued
p@tically vcgctable dyes. Iruils lile b€Eics
coloEd ma1&r s€rc @lLor.4 bono4
i|meBd, quing
6d knoM roola ed vaiou sorrs of
and lhd cb6s .nd ldlite nd.dals \*!E
in rh. nrn dycd produc!!
'ftis
M
rlc
sy
by
*,lict rimy
|w
dy.stufs w.rc ayntbesizld. In $di$ic,
ndy Mir€6 have contim€d ihe iifomalion
of ovd on. tholsmd sourt s of dyes t361. Aj ine dycing indutry bccam. m
imponld stor of bui!6! dycs g€r @Ep6r.d i! ffi of pmfirabitily whcrc rhcy
id@dn d B b.tGr rLd othcr!, .nd $D. of rhcn ger teeiutc<t bciDg !$!. Natural
dyes
ued includ.d vegeilbI., oinut, dd nincral
dyes.
In 1856, St Villim Pdtin mdc d €nomoB disov.!, rhal cb6g.d ihc *orld
dtling Fldc, He dsv4cd r[. @lo. !@v. by chde *bich lhe 6rsr syniheri€ dye
B.
He Ncd co.l
new pdlhr in
qle$ively
ed
|ar
i!
his
n
thod for rhc dy.in8 of thb n.w cotor ehich
haiy ei€trritic devetopnetu md
sd
torlay
rhe
advdcd in syntFtic
c.Btt
dycs that
de
I31.
l8
Chapter 1: Ceneftl Considerution
r.5
Dy.bsTtdrt
covls a wid ren.s of subjech es!.cially in rh. de6 of
physical cheiiisty. Theorcticdly, 0F pirpoe is ro d.livq ! s€t of rheoi.s rh.1
Thc theory of dyeing
cldifyh€F om&cc
!c lble
to
L6.1 ThG
This is
of
tugni?rd
dycins
F.tho&, with ttd h.lp of which oft
pEdid thc rcw situaiion for ftw Foce$ [38].
Pbyli.Gch.blol tup.ct,
&. pres
whjch prcvides
of ihe Dy€irg
q@libtiv.
und.^t$d low dy. noldcll€s pc@lla& inro
rhe
Proe$
.la1a
nbq
io whioh it is posible lo
udsilrd ihis we
dycilg m be sMied to
6d.BLnd .3 ir hA' surfacc !rca, diffulion layd Ed .let'ical
In phrsico{hcDical apect th@
wld
dyc is in solutior fo.
e
To
1391.
sMy lhc aurf@ oflhe fbd. A texilc ftbcr duhg
should
@
double lay€r.
fivc silgc5l
dr€ilg
WEn dy. omc closr lo diftEion layd
When dye
i! .lecFicd dorbL hy.r
Wld
dyc is
Wh6
dyc is in the
d sufacc
fibd
fiber for fixdio! alolg qilh @udanon. I! rclctiE, lixalion is
ready 10 gct in hc
chcniciuy wNle in othq
ces
il
I
A@Mulsdon of dy. in thc fibq
stc.dy
ptt)lA
io gct adsorbed
by me@ of phFical
*iich
p@s'
also mcrtioncd
which i5 golqn d by chonicai atr(l
6
"tute of dv.itg" is
plrical FoFniB of
I
dve ,nd
tber llong wifi condilions of dy. baLl wtich include dye @nceltration' elcctoltle
@mna1io4 tcnp.6rN, Ed liqbr raiio.
l9
l
Chap@
t.6.2
TL
Generul CotLtiderution
S.X Ed.ct
&d.ll
fib6
utud prepcrty iltd wh.n n b *!n6d it get3
!.srrire chr8. *nich L ttFh a z.i. pot i.l. fti! ctdgc i!.!oug! io FFI
CotLo
@llulGic
nlec
a
negldrely chrs€d dy. noleulc! which
lubd
of lulf@te gE|p3 is dirc.tly
e.lE
ro sulfoDte greupd
(sorN6).-rhe
FbFnion l io rotubility hn rh6 dy. b@@
nor. Fp€ucnt wirh fb.i sufa€.
Oj
oo
oo
o
o
figrFr2
Salr
Eftct
in DJ,.i!g
oldqn tiii Flblco ett ! u..d io rU in dre botb $ lt ediu i@ Hrrlizc
r.DpoElly rh. etE polaniat s rh. dye nol.cul. @ lpproach ro tE fibq io fom
cord.d bold wirh tlstis dFi.g Gtl.Flt) t4ol.
To
)0
Crapter
l:
General Constderotion
i.53 Dy. R.bnab!
For
ctEy
tbich
fh!
iEld.
OcE is 5 rpccift
dr *ni.t d.iled dr
$re iliariot
tu6
ed V& da W.d, foB sit! ,otubitiry
thc fon! tu th. .frliiy of a dr! which L@.d
iooic, lydmg.n tondilg
@gur.-!3). For a padicular ruhgrate
., $bst llilrly t{4.
t *u @*@-@
.lt di6
Dipolr
ntrFls
1,6.a
to
6-
6+
6-
H)&!so-hodng
lirr.rlilg Forc.€
CoDbo! Tahniqls ol Dy.ile
omlfr.rtrilg pt!.G$6 oft xrit., dFiDe co bc dm. .. sry lrse i4 i!
llc fotn of fib.r, rlra frbic o. gm.o!, d.ladhg on . cod of pro.6 ,rd
requime ofrhc lrodtcr qu.lilr G.bL-4) It2l.
Duing U.
2l
Chapter
Trbl.-4 Difeient
I
Genercl Co lideration
Stagca of Dycing for Cotton
n6trtrlolr
rnd
Dm$.ckr
Mon@ y dy.irg n.thod
Dtling ld8 b.foE s.er t ginr
6id lh. nit of f$hioD
chngii8. Hi8h p.rc.nLg. fih.r
S@id n6r cody
n
t
lhod
DFing b.foE 5@r gia
Mi4 in. rirk of fahion
.h6gh& bll ls rh{ for rr@*
Lidiad
io
gmc.l'
of 3anplc
t2
l:
ChaDter
1.7
R4tiv. Dy..
Fib.r
Itcse dre
e
cdor orgeic
nwl@plilic goup6
ibpiortd
s$ing
o
thai
e
coql.ol
boad with hyd&xyl
sDhi€ h
ffir
dy6 @ prcfcnbL
!o
10
fm a daldt
t doDi@t
c@rribdi.s fd
*it[
chss
of
R@drc
ilt siryilg
q/.
@ld b.dB
fm
pspc6
1491.
Mol€crde
ih. @hr
1501.
hrotu gcd uhrrn.fho,c c@hibutiDg for n.inly colo..nd ruhrst iviry [51].
Bridging group conti.ls tbe
stltm to lhc chrcm8m .nd .x.n3
sigrific&r inohc.s
eriv.
on
r.erivity, st bitity ed rut lmrivity;
RC = Reactive gmup witb
S
ralE !dd!d
dy. mr only fibca Drd. of ellulos bul sko
filGra
B=
a!.1
of it
of sinsle or nuttipl. honds I4El.
r.dssc.nd flc .I|F'* D@a s tte 0rio8r FquiE
Moleulc of @lirc dr! i! coryo€ed of fouryins sro'p€.
=
bc.N . Frt
q.
fit
^( ^uohrcne
(
bond wirh
D[o6plFrcu atoo of E liw dy. n le a
ofcellulos., .nim of polydilc or n MpiG sreup
Ceboo
id
.ble
chair5 wirhitr rh. fibq to
f!rtr.35 t43,44J5,451- ft k
ellulo* tib.i [44.
of preteir
$bdlMs
Flym
th!
dyc for
'Ihe
Generul Consideration
lariq
= Water solubilizin8 grouD such
gMD
a
fffi olrldr bond *iih 6bc. *ni.[ .fr€.ts
sulphonic
eid
atrach.d on lh. !ryl rings
oflh.
chDmoed t521.
27
Chdp'cr 1: Cenerul Conriderution
Tbe
wrd luohremc
is deriv.d
tuE .lxcitr s pFfix auo n !r! inc@$d dd
cbrcne mems color so rh€ compter mtuin8 is color
Au@hrcne also dBdib€d N @Iigrtor
ed
@lor modificB, ret!.ctiEly.
aod
rcnsli8.ror s
ThF e
electoN when bondcd witi ctuonophor.
inc6s tj3l.
iotrizing
luochrcme
gbups of aroB with no.-bonding
cd shit
ihc wav.Lngth and chans$ ihe
htensiiy of 610r e.a -oH, -NH2, -NgCHr, -N(CHr)t, ddehyd* bul crml i,npan
t!. color by itsctf to ey @np.ud. Dc lo this lt@n dso called s cotor hodifiG
oisrFts)i541.
H,N<
>c< Frtu,
:,r\:
tl
lhis
is Padlosanilirc
etich is
NH,
"''i"o6G't"'
M€rhyl violcr ir fdtrd by rhc lddilion
of fou nethyl grouls ed it! huc is
N(CHrb
,",c1"
.}-.-f\fi,cH.,, '\,)
By rhe addidon or sB ndhyl srcups
puplbh blrc dy. is foEEd which
is
hoM E crysrat viotcr
T
N(Cr{r,
cr,crr"
$c-$fi1cHr:
-n '(
ana addirion or *v.Drh mrhyl ercup
m'tYl sr'cn dY' is fom'd
N(CH3)3
FlSuFrs Chllgc of Color try Aur(o<lh@
Chrpt.t l: Generul Consideraion
rt
y @ fou typ6
.
of3li0i
hwtqgItr
(rbqFl6):
B.liocbroDic group€ e U@ Sroupe which ..Ne disphcdq of
svcLngth in chrcrogo toeirds tongd wlength dw !o which &eF
@Itr plodr, tbis 3hin in uEt@srl is Ltu€d s b.rh(h@ic alin or Ed
in
a& pdrE ), s@trdry
.nd .b$rplion
ditu sor4s
. HyFNbFDlc soups cae hrTshmic o bl@ lhift. thb
shia
or
rau.ry
is a
,Iift of
uELneth lrd tigha ftr&, ,,& stv€nt .fld.
Eyp.ftnoLh .trc.1 is s iftBE in absorptid ir&8i9.
short .
.
.
fitpo.t|uic .ffer
tu
a
a .korpri@ intdoity
t551.
t"l
EI
t;l
H
EO{'
Fis!r+|5
Shin!
iI Wrydogrl ed Absiptir
25
Chupter
I
GencrcL Consi.letutiok
chrenoptoc @ntaininc cdFurd ir rnom 6 chDE%o (cteito. &cplo.). li is
th. donatic strEtM coDrdining b.nz.rc, etbn cn€, p.lylen o! !.phth.l.re,ilg!
t55,571.
_N,CHr
HlCN'
( FNiH,
z)
ColoEl6r
(1)
Chbhophor€ is
b,
(2)
Uetulted lircrionat grcup rat .xlibii ctsrrcnic
abeaiion i! W-Visibt. rcsioi [58]. fte colo, or hue of
dyc is du.10 ctuoEoDhore
CI$165). Th€F @ lw BF, ofn.
Ind.pddor cbrohoploE i! t sirgt. chrodoplbE wiich qPalt.
h
k, prod@
olor e.g Nihoso goup, -NO, Aa glup _N=N_, ed
orno sd pard qlinonoid
@val.nily
D.pelddt cl@Dophoc
e
rhos which rcqliF bon lb!tr on ctmhophor.
to
iEparl color i! chrcnoscn .& >C=O, >C-{1
groups ./.. Accionc is colorls
!s it
nes only one t tolic
Sroup ed ao u.loiEd clccron bui diaetyl is y.ltow in
@lor s
tl hr5 tuo c.rtonyl grcuF a.d havilg rhF.
upai€d clccr.oN whil. tikctoMid€
ori8ir thr wbonrt ercuDs is oEDs. ir @td blvile
6vc @p.iFd .l.crons
l59l
c!rcmophores c!! ale be chrh.&.i&d
s n |,t coD$q chbEoph@ .d
@njue.icd i,bond syst m ctuomopbor€,
bur lh.ir qplanalior
need norc ..scdch
T.blcs
Md!lamptq
AntnEq!in9nc
_Eqdecydirc
P.r
Aa-
rSG
Dirribdo ofch.oical Ctas$
90
2
l0
20
9
tl
in Rc&r,vc Dyc H@ S.cbr
t6
5
37
27
2
42
42
43
l5
1
l0
t
I
26
Chapter 1: Ae"enl Considerction
1.7.4 Azo
C|lronopboe
ft.
chsmoPhore coniaining dyes .re thc most
inPon$t class' contributilg
(rt8ur.'l?),
and hlving b€ed rcs@ched
@
Nud
over 50% of all ndkciablc dyc!
dy. Ae dy6 .otrtain at l.an on. eo grcup or
two (dia?r), thrc. (tieo), or morc s.ldom fou (tctakis@) or norc (Polv@) @
grouF. nlese dhplify the !a!i stuotural vdi6bili9 p6sibl. in e dvcs' maidv
norc thm
with
ey
lolye
othd
PrcF
class of
dys [42].
(}"Q)
I
-,o
..
N(
r
c-rHr
9Hr
>N"
")\.,41\/:
c43 crs.oH
>N.
crlt oH
,*O^nefl. *<)
Gv
tnO"q
sorH
HOrS
sqH
C,)*n{
(r!""'i
sqH
6
IiglGt?
A& Dye!
C. L Solvcnt Ycllow 14
(l), C
Dispqs Blue (3), c. L Rcactirc Bom I (4), C,
cred
26
I
I Disp.ercd
AcidBlack I
13(2),C
(5),c
l
l
Di@t
(6)
HalochF@sn in chrcnophoE
wh.n a naterid 8d chsge in @lor a
b. e.n in pH irdicaioB, lhdn bol4uld
ati!* ulu.lly
Tlis chEeldisli. cs
stlu.he cbangps whd lh. pH of thc ,wuding cheged. EMPIe is
phdotphtholeid a pH indicstor vhos. stuotw s.b chmgc on chagc of pH
the pH ch&g€s,
(I!$rcr8).
21
Chaoter
l:
General Cottsidention
E2:12
Ga2
pH
(D
nguclE Hal@hremiu
in
Chrcdothoc
l.z5 Bdddlg GruD
d lintd grelp 'ilbdn*! cLd$o tld dE tEd of tlt doLtulc
rb.Ffor. in lh. pt!.d. ofrtlrli lbc ldirs gtoP d.P.nt eid ! htdDsen id 16l i
B.idsiq srurP
I idancca
l.ff
lhc
dfrtiy ofllF dy. e&
NH
d NMc.
Rqcdv. Gm|lp
Elerolhtlk E!.riE grelp6 t[.r @trlsb r nEkohgic lc.vi4 eroup e tb' tnlin
cdloPrt in dF !!t!le lo nlc n tu to *!b bv gdiig b@d'd @cLddv eiu
Tlt EdiE g10146 of diftild OF of !*irc dvd @!'i!' or
differo cbdic.l tllEtuc dE lo rtic.b. *i& tu8. of tll.{ililis {! lhdq
suD6t e [62t.
2E
Chapter
I: Gencrul Comiderction
ct
nRn
or'^{nn/"'
.$ *l{N,LNtu.
(MTD
(MCr)
F
cr
"''ti^|
Dyett|t\Nacl
sl
s,
sr
(DCT)
DyeHN\r-'\rn
t'Y\1"'
"'\^\,
oF-tl{*xar
*
3.
(rcP)
(DFCP)
@ca)
NllR
D€Ors.clrcH?OsOtt
s?
Drrols-ClFCH,
N4r,l
oyororll'""r
d1co,x
Sr
Nico.i'yltiBr.
tw Ni! clss! ,'e cold' @d bot{vcilgbt"lds I29l d
o! lh. Fel.@ of how ddy IEbGB of t ldir.c Srouls in oF Dlc'ulc of <lr t'
momtu!&dot l hsvilg oe i.!.iiE grow stilc ,t-fe1io!.I dv. is !NiDE two
E!.tirc 8rc!p!. Thc sroup3 @uld bc ainilt (hono ,l"nedo!'l) q di$inild
(he&m rFnNdoDll,imx.d ri-tulotiold) G.bleo
'IlEy csbc dBtibutsl ido
29
(r.lT)
Chapter
TrbL.
5
Ispoi.lt Rctrtiw
Dy€
l:
Generul Considercnon
S}lrlo wilb T}?icd Brlnd N.d.
BEld
Sl
32
M0ooflDroLia?ie(MFT) 53
TdchloDlyriridi!.
64
Cl orcdmuor ndnidilc
55
Dicblooqujnoxdirc 36
Sulpharctbdsdpbotre s7
Sulphato.thylsulphonanidc St
@cT)
Monocbl@ti.zi!. (McT)
Didnorcdein
Ai@@@hlororieim)
,tddolonuorriei!.)
,i(moronic.riDoriaziexND
[531
t!.e Dy.i!8Tdp.
lvD(
Pr@id H
cibocron F
Ddn&cncx
DriDrEn K&&
Irv.6xE
Rdrzol
Rqn zotD
prccio'
30'c
s0
t
50'C
95b
40t
50t
60t
50t
H-E
S0 t
NomFN ruge
ld0 t
K!y!..lon
Sot
,,](sultt rocthylsldlhoc) R.E DI RGBTLr&! DS & c/Elm|/SFM| 60 t
Monochlorotri0ziGsulph4oethykulphon
ulphon
pr@ioo
SMifixSupF
C
Di0@Dpyrinidiicdlhdo.thytn{Dlon DriEraK
Mo@auorotiuilesulpbarocftyt
Cib*rcD
SOt
E0.IO0
.C
4&60t
30
Chapter
T.bl.? Comcrcial
surllid
R€@liva
I:
Cenerul Cowiderution
Dys wilh Their B&d Nmes, Cowtry of Origjn ord
[2q 64]
Oriqi!
EvdliShl Chcoiclts
Ktsco
KISCO:
Kni
Pii<i$a
Dy6
Ltd
(KDCL) 16']
SC Dy€stuf &
Clai&t
Nippon
Krytu
of i ury is b€sr io !e€ iE p6t hislory .t
dd.lopndl n& in @!tet1$ith rle {nc pedod. h &c fo[owi.& rb@ is thc @in
rolgeiztior in lst @ lo thb d
To ude$hrd tlle pBenr
stlt
3l
Chapter
l:
General Considerction
TrbbE R€o.seiati@ of Cllo@t Mrauf.cruer tndu'
r
E!roFr drshrDrtrlnctoFr
Jrp.N. Mr!ar.rrR;
Go..ally rhe lerj!8 greup's qudig is di@{y
pDportioid wilh
ColrDon l@vilg SDLpc ar. hatidB
(C1.,
tbc
F, BO.
r.7t W.t.r Solubithhg Crolp
Cellulos rcaaire
dy*
s!!ly
coabh l .4 sulplo srcupr.
,ft*
greupE
at$
.fcct
32
Chupter
I
Geneml Conrideratioi
l.Z9 M.ctrnlrE of Racllv. Dy. trllrtlon
Ih*
dyca
le
sb{lrat udd $ibble
cap6bl. of rcaciing chchlc-rlly wirh a
s coval.nt dy.{ubrat bond, Th€ chder.ftlic
st$ctual f..b!. tu lhu lI. possion oI otre o! bo.c rc..tirc srcupir$ of vdiou!
aptli@rion conditioa to forin
tinds. On th. bdsi! of E!.tion ncchldsm of
A-
@tivc dy4 thcs tuy b.
l|.t.ro-Asurlc Nucl@pllh
Dy6 Radhg Thmud
SubrtltudoD
@tegorizcd
R..ctio.r
CNmEi"i.yl h enich !n etivslcd labil. hdogen rubGttucd (C l- or f) or ncthyl
sulp!@c or licotinyl leaviry 8reup rcrilatli by ad dja.cnt Dittog.n aton lhd
urddgc nucl.ophilic auhstiMo r.lcrior by a elluloer. eio! sd ellulo6e iD i!5
u.1ion wlh !.!.liv. dyca bcbwc c .l@hol. Cdlul@ i! subs.qhdy ioliz.d in
dkdi@ cddiiions lnd crn *t s rucleophilic rtg.ar rnd shos $b..Cu€!r
lwtioB .lp.cislty *it! &id hllidcs (nuclcophilic sulsdlnioo) (s.Lhd). ft.
o.drnis
ofnoclophjlic ruhdintion
CEIOH
+
i3
Ns:SOi'
*
CEL-GNr + N.HSo{
-
o.Mku.,6i)
#9lr
!g folloqs.
cE['o Nt
x
ryV\.o*"u"to..
ri.o* *n"ct
x
+
oH-
Dy.\f\.ro-H
ri.r'*
*Nacl
x
Hydrctyzd dyc
S.bcoc4 Nrclcophilic Subrdnlion
J3
Chaptet
Sld. R...aloa ol
R.dis
W!6 Hctirc dy6 @E€
hldrolyzd R
.ti!. dr
. $b6|r|rtiE ditlct
bontlcd
dyc vnich
vit
drilg
h!!
ir
loE
w.i.r |!d dtdi gd bydrtyrcd $iilc
.d!.rt
w$i!g.n
.dFing
d by rhc fibcf
cobl mlberr
t! .riE dr. Tb@foc, ir i. tt4sty
vig@ul
B.
codtcr
duins
Gene,al Consid.rution
FL.do!
Dya
in
l:
ro
bcqu*
ro urutdng
moE
n
ihlr
hydiotyzed
$fu
bchlvd
rh.
tiL
@vddtly
a!.rirt
dyc by
[53,6?,6E1.
Dr6 Rocabr Throlth Nrcl..piluc Aildtdo! R..ortolr
o:.-$-c-cx,
8H
+
cEr.GH
+
*-f,-34o,-o*ur*
o
Mchrla:
,{",
\
?
Y"F.
D,.-fi-q:'c-9-sojN.
:
(.)
I
(b)8H )\
ll e"/
I
3 t,
qr-fi-c-c-o-c.n
"'
o{tn
3"
D.-fi-crFc-o-c.
",
o
-
Sch.n..s NBlcophilic Addirion Re..r!on
'Ih6.
trF of d,€ !F lold i! t foln of 2{ulpblroc6ylsulphonyt prEuM
(s.tdct.In |c fitn d.! ofEccbllilm.ltdi i,.dd!d lott PtEuM Eflp..d
cbd8.d il ilio
-linLd
l!.
fom of..tiv. vilyt su|!hoG. Vilyt ltdphoe dy€ in snich !6
|ln$a!!ld linyl gtlrp lllr r.rcB l{itt cctlulos. by rddirio! ro thc doubt.
bold tl,59l.
lloli .l& eer..idic disocidioo of rbc bydloxyl sDup. i! rh. eluto!.,
rlrultiDs i! rb. ccllulosL io! (CcU-O-) tht', l! dy !o r!3ct wirh rhG dF I?01.
Coddporlri pDgte.. t v. lcd io Oc inrldu.ri@ of t@Gbinudioltl l!!.tis
Tb.
l4
C hapter I :
M'e|tns
iderat ion
vilt! tso Donochlorotiazinc grcu!6 ed hcbo-biturctional @tive d}ts by Ning
no@.chlorotdeine plus viDyl sulploE bollt !o eihaM rh! dF 6xrtjo! on Uc
ebrEd. ud6.tt lim sndilio!5 tom 5F?096 wirh orc @rivc srcup, ro 8G95%
witn
1.8
im reriE goup.
[63].
Fh|t|on of ri-fuD.tlonrl R.rctiv. Dy.rl
Firdion in the
ce
of
! rt:inctional t
acrivc d)€ by pld-balab pmc6s is good
conpqF to mdcfiDclionrl dyc, {s oE r.{criv. g@p
s€
E
of,FnDdio.al
!s
dyc
a a mom-tuncrio.d E..rive dye,
l€aving 25% ua-!wLd Thoud, lle ladly hydrolyad but slill ir is @tive in naturc
6 re0a1 frirlhd. lhrough lh. s@d M.rivc group (R . Cons.qucn{, aloul 94% of
lhe |slout of dye gcts boutrds to tte fibq dd jus !M!d 6% n hydrclrzld GiguF
l9). Sihilrly in ealNn dycilg th. dce@ of lixarim is lowr rba rlaa of!6d-b.1ch
dy.ing d@ io the fet thal thd lol3l dye d@s ooi cotircly exhault onio rhe 6b.r. r{bcn
@uld Eact wirh rhc 6b.r ro lhe
a
biturctioml rcacriv.
ror
thc.quidot
dyc
dege. (75%)
cxlaur b
85%. of
{hich 80% fixation
6
be achicved.
dcgcc of o<hau.lioD, *rc fixlrioD of nonFtu!rction t dy. on
al@8. oily to 60-65% .nd lppamt sDounr of dy!
us€d lo bc rdsbcd
d
ofidui.s rh.
Chapter
l:
Geneml Consideru!ion
B
HydrolysisE
Dy
.R
25y.
HO.
25Vc
Dye. OH
HrdrolFed
15Y6
C.[.GDrc.Rt
Hydelys!
15'/r
Dy..R-O-C.[
25vr
HGD,GOH
75%
HO-DroO-Cell
dts ,tr/.
Iixcddr: ---J:*
FigurFl9 Fixaiion vstue for Monotunctional
dd
,!fiDclionat
Reacr,ve Dyc!
Hwing 75% Fixarion p.. Reacrivc Greup
L8.r Dy. ADpti..ttor M.ltodr o! Frbric
Vdious n.rhodr are ued
b
give color lo the fabic &cordn8
ro end use
ed batch
ui! €i.sori.s.e dy.in8 ed pdn Lng. Drlins irclld. cxnaut
dyeing, cold psd-barch-M5! ofl or contnuous
pld-sree-Mh off.ld dly ncrhod!.
Fixalion by dry hc.r, sltuated st a'l
o, slFrhcarcd se.D my als be us.d
@ftmlg io lhc rrF of ecrive dy. us€d
163,61. wlilc teush p.irriog ncrbod
qMtty. Te
dyq
6
bc applied in tocatietl
this !.quiB rhickcning
fo.d wlich h tcquir.d !o nakc desjsc on fabdc.
.geDr b lDk a prinr psr. wi{! dy.. Many
nedrods ae ued
deFrdonlhc quaDrity offabri obepbduc.d.
Vhco @c!vc dy6.rc ro b.
Filcd
tha rhe lelerion of individuat dy. should @6idcEd
oo rE bsis lhat it slould b.
stabl. in rhe pri !ss& lrd rhd! shoutd
bc .o slainjrg for rne 8.oud or oth.i @106
.r it ..r chrrs€ thc h@ oforhcr @toB iD lh. d6ig,
sFci.tly oplosire @loB f?21.
l6
Chaprcr I : Gekercl ConsiderutioD
Co iloou dicinsa& Pld-Thmo fs
or
Si.d
fJ{.
s.nr-Conttbuu! dy.tng{.8. pad-Batcv Jigiqon I?31.
B.lcn rtu. E rBrton dy.iog-e& ViNh, J.r, p.ck g. ad Bcm Dy.ing_
P.ltrahg-a& !.int-IrEmo fx [24].
l.8l G.D.nlSynthsi!
ot
Aa Re{cfivc Dys
Boih orgdic rnd irore&ic @n$itucnh
bd
rhe
squ.ne of Ew mrredal Equircd
e
nee.led to
nsk
fo! dye slndrsi3 i3 ss
P€irol.ub --> ArcEr{c by.trocrtotu
follow tTJll
-> tnte@.dltts __> dy€i
L
gcn€dl s)rfbais of dy6 s1rn in ! @ror,
lh6 ecl dri.d an r flrltio4 aid
@nbin.d vilh orh* lddirives to yietd lhe tml
!rcduct. The srlrhsis froD ftrst sleD
includes .actions such s sutfomrio4
halogdario4 miMnon, diazod4tiod, ed
@uplinc
(S.tr@.{),
which is @n1in&d by
spdstio!
puincdion by prcciirdion, dd cryltallianion
pr.c*e
I?61.
(+x
(l-\ >NHr -_- ( \>MN
sfor .Pnniry
einc
Djeiun slr
ScIod
Slrlheis
uar hay @Eisr or
of
Aa Retirc Dr!
Gcneral Conside tion
r.83 Dl@ Dd Corpnlg CoDpoodb
For thc ptuduclion ot a?o dy.s, diszo conponeds cln be spdar€d into rbe
ed
slbstindcd
mid.3, ed
suUonjc
l:@s,
lt!
eids
e
dliG.
eitinc
eilir6, .rnirc bcMyl
gtuup is mrbthyl miG sd mphrhyt min.
Ex@pts includ. rotuidilc, .ilre
sulfodc lcids. Aiorhei
The @hpoudr Pr
s.n.d in (FiguG2o) fmos by thcj. @mon
.xmpls of Dphrhyl @ine sufodc aciG and @ ato be us.d s
s9,rhtr,
sorH
t
so3H
at{'*'
NH,
NH2
so3H
'o'1--A*'
Da &'d I
solrr {
HOrS
sorH
sosrNI{,
\-\4o.tr
sors
sosH
Dabl aaid
so3H
I
HOrS
Fis@20 Exdpld of Nlphtbyl Anire Slrpholic Acids wirh $cn
Como! Nm.s
Mth Anov hdicatirg the Colplirg posilioi
38
Chapter 1: Genqal Cors ideratiotl
.td dphllob uuUy @Dlc .atily lnd Fotndry lhln !nii... Tt
pronpB of t[. pt tuls L cooplc iis B th. nnb.B of hy<Lo)Vl giot!6
incft.rca In uhoophtol rdfrDi. &irk
s H, lq &d S &id+ oriatdion is
Phaob
't.b
clwlilg m.diM cheg6. o|t o to aanno
posilion i! g€nins cowled in eidrc m.diu whil! i! e .lkilir n€diM o/rr,a to ih.
hldtoxyl grup b thc poritio! {,h@ @udin8 oc!u! (tlgrF2l).
intcos.ly influlnc.d
2
r. lhr
pE of rh.
2 oJ
9H |H) r
,T'YY.
Tn11
ntTY)-"
XO'S"\"\-^SqU
z 9H Mr.)'
:'
z-'z'\
3Rt
\-^/
I ta
sorll
.
n$!..?r Vdi.Iicdi!
$&id (cbic|go lcid s)
CoarylirgP6irio!6tyrhc
l!fltte
of pH
39
Cha|et L Geneml Cohsideru!ion
l.E.a
Il
is
Eorlrc.D.lt l Colc.hr
alsslrl tt l @tivc dy6
ri8e in tadcs
wo*
in the
for Recdv.
Dy6
is th. onty rug€ for cellulose
.dly !a!r
of 21d lcnluy.
ft6c
big sb@ &on orhq ellulosic dys lit€ suttu dtcs .Dd
basis, vais on
pdc. ald application, ard diEcls
dye! b th.t lbey
e
on
highly polmilg @vimM.nr
lhon apllicdtio! on
le\tlc
is e,(p€cLd to
dyc! ate FEdictablc !o hr€
@ic dy6
fash6s. Bur
eiitd
*!ich
in ihcir
on
ovitlmalal
th€ d@stack
ofthes
indutdd sy
hcsis
or
It Fquire hiSh !es. of sdi (ladicularjy in
cxhau$ncthod ofpNessins), atoliislscd for fixatiho! lubstEt ard ligh usag.
of @. (in printing), which is difficuli ro movc tluing reaiment of efflucot.
MoMw.,
subslrale,
ihd
@crive dy6 @ facing @nccN tik. prs..@ ofad$d{ble oryuic
balogeis (AOX) vi&in rlc dye nolecul€,.xo€s of wate! @sMprion, pEscn@
of
h.$? rnaal ion
h
dy. hotdl.3 (Ct, Cr, Co), €tativ.ry tow fibrio! lcvcls.
dimcdly in reno{og hydelyzd rc.crirc dy., and Gooval of olo.
fron efflrcnl.
Chapkr
1.9
l:
Cenercl Consiclefttion
Pr4bt Ptul..t Plu
r€*eh in dyc
dminty for nw g6.l!tio! E!.rivc dyB that d o@ut r all ovibMdid
sledads d wll a cd fulfill th. Equircmmts of the cwlomd (i.. Qulity
r.quimds). IhcFfoe, tb@ b a ncd lo d6ier
@rivc dy6 sith ldldc.l
Iltc
solutioD
of lbove-mcntioned prcbletr
re
lor8d5
dir.cred
'w
&d envircmdi.l satisf!4tiod. d,r-MCT dyB, iniriaUy Mk€r.d for drring .dlulo$
@DFn !!l io
P/C
bldd!.t long-li$o.hlio!,
e foui lowi! sclivity
'C) &d hish in eubslaltiviiy- Duc !o which some dBwbeks
N
(fxilgat
E0
th@ likc l.veling,
wasbinS{tr of O. dy., aad $itability to "Salt-a1-strd", inprevrin dl in lhe strucfuE
by irlrodiclion of rhe di.Mine
@upling @bponds. Du. to
the dyc is cxFctcd.
li.lins
pR@
of
t\.
rwo chrornophoric unik wilh diff@nl
lid.g. imprevmdt
of Mino
'ftcs. $re rucc.sftlly drkct
d by
in fslrion
of
Zqda uder th. PMioo-
HEXL bade naln€ t74. Irte wiltion in rh. conept of 6b{non@l oroEi4ire)
st$ctu! is ldscr but thrt po$iblc tugcncnis e thft (S9-Sui RNH2 - aryl
mine, .NE-X-NH- = lintiry eirc), Structe Sl0 is ihc gddal nodcl srructurc to
be srnthasized wirb
diff.Fnr bridging noi.ty
dy. Byrdretdcal dboul
coopoftDl
fton non
th
center ond
rd
coupling
(Mpo@ts. nis
cld of thc nol@ulc. wllilc blE 4d 8!en
chrcmoso (su) t581.
e
uualy slnthdizcd
IEfl
-. Cl
l.K,N
ln
NH-X.NTL1
tDy.FNHi\
,.N
\H(
..
H N=€r
(
tdveFN-(\
.)
}K'l'{ ..-.....-r
N
;-
NH.R
*-to"t
H-X-NH
of
coli.in only y.llou o6ng. or Ed monc@
at .a4h
@
t!.
t'F.
I=f'
ldvcfNH(\.
"
}NH{F.=t{
-N{,i'r
R'HN'
"
sr
Ntl'R
l:
Charter
1.
A, Fntz, t. Cani Co,er.. r.rriler,
lrtss, 1988, pp. 1,3,5.
2.
B. P. Coibn&! Ierit€r Flbq to Fabtic,
Oehercl C.nsiderction
Sourh
Melbom.r Oxfod
d.d.,
U
vchity
Sl[eapoP: Mcc.aw.Hi[,
r9E3, pp 3-4.
3.
4.
5.
6.
?.
8.
9.
r0.
ll.
v. A. Shc@i, "Techlolory of pian e,', ia ?..tuoto&) oIT*tit. prMsk&
Vol rv. Bonbayr Sevak publicaliois, 1990, pp.24.
nnpr'/*w.$rib<L@d/do./In-,Ihe-E&li.n-Citi*
hlrp/&w\r.swicofil.cod/producls/00lcotton.hrbl
e. zeht. "Biochcmjshy ofih. Fibq," lo pr)rrioiog olcoion
,!. 3tNn!|,D.
Oost rbuis, J. H.irhott J. Maun.y, Ed. New ydlc Spring..,
2010, pp. 3?E.
htb//coilon.missoui.€ddctsrooD-physicalyaostructurc.hrll
hnpJ/atlaboft*tiles,blogspol,oD/
hnp://@.witipadi{ols/wiki/C.llul6c
A. C. O'Sulliran.
.!.llutos.:
rc Slructule
Slowly UMv.ts,,, Cetulose,tgyt,
4 W.173-207-
v. K. Vshn y
Nairhei. ..Chtuicat Fbctionaliauon orccllutose,,i!
C. ulos. Fibe6: Bio- and Nano-poruel Corlor,r.J. S. Katid, B.
S. KriO, L
K8u, Ed. Loldon: SFieea 201r, p0,46
and S.
12,
hitp;/&''!!.6g!.!iL.du6e/Tcxtilei/fttto!%2ofibcs.@
r3.
A. D. Broldb.nr "N.n&al C.ltutosic Fibffi" in Aa!,. p.r,
r4.
15.
, ofT.
ile
Colrrzr-or, EnSlard: Society ofDy6 ond Cotdbts, 2001, pp
?2, 73_
C-Fu Liu sd R. carg Su . ,,C.ltrtos.- i^
Ceteql Sbtu 6 a Reewce
lol
s8taiMbte Bionathiats d,,t Biof@ls, uK: Elwicr,
2010, pp. l3E
K. Xlnide. Ceurlo$ a, d Celt lote De|rath1, i4okcu!tu
Chuoctetiqtioh
and its Appticatt^,N.]Jjtdttuts:
f6.
ctpt
S. P,
Mishii. ,{
f.r
r@*
Et*vi{
B. v., 2005, pp. 4E0.
oJ Fibe, Srcte@ and
Iectbotog,Nq
Dehli:
Nfl
ag. Idenanons! publisheB, 200j, pp.8j
42
chafler l: Geherul Considerctior
17.
A. K. R. Ch6udty. I?rrlr, Pre\atbn oru| Dycir& VSA: S<i.ne PublislEr.,
2006,pp.134,19
18.
J. Sh@, J.
?dk
Procnaal dtEfi& Socidy
ofDydt
snd
Colouislr 2004, pp
22.
19.
htlpr/.n.wikipedia.org/trikiDyehq,
20.
htlp:/,^rw.scribd.cod/doc/4?970032/Tcxlilc-Dycing-Th@ry_of_DyeinS'
clssindion-ot-Dyes.
21.
22.
23.
24.
R. M. Christie.
Colou Cir.r,!lr),. U.K. Royal S@ie9 of Chmislry, 2001.
htt?v/€!.eikipedia.org/wiki/HslrndHSV.
htlp://kws.atleti&sc..orgldycing.htnl.
hhp://w2.chdistry.nsu.cdufeully'rcuschr'inTxijmvspccLpy/w.
ViYspeLum.hftr.
25. htlpr/\rwj6sm.hicdu.c/...@uD/n4hllidpllvidlzgri.ds"htn.
26. hp/w.!briq.uloD!to..d?hytE9hl/Cautcs9620o?/Arcnbf/.20*ie
27.
R
G-
Ku.tni,. Coiq Sr@. drd ru Dylr,oa Ncw
j*y:
Joh!
vilcy & 506,
2003.
28.
29.
r0.
3r.
htFr'/momgnpts.iN.t/ENc/MonoSnphdvol99/moo9-7.pdi
S. S. ZMdaNi D. J. D.c(*/rc,.Ch.nical
Hfttples]b
d,
10.
U.S.A: Cengage
ledilg, 2009. pp. 96?
R Khd md U. C. Ba.\... tucolori.atlo" of Ap Dra b, Inbobtlized
Eocrel,a. Ed. H6lice Atlcag Erkul. Nw }!* : SprinSd, 2010, pp. ?4.
Ault a G.org. T., R. N. ShEvc, ; ,. A. Bfik. Snr€v€'t Chenkal Ptu@s
lrdur,?c Nw Yo*: Mcclsw-Uiu., 19E4.
32. hltpr/tdtlnfo.rcrdpBs.con20ll/1104/cb,e!ificdion-of-dy4/
33. hitpr/\'w.anisc.cstion.con/Coloudndex_Inrenaiional_ci.htn.
34. htp://w.@lou-in.tx.cotr/.
35. htlp://w,b€rbsoci.ty*tu,ory/Dycing,hh.
36. htlp://w.cocfincd.inJo/pdgch.5-History-DFs-Din8-lnd6troldWodd-Cochiieal-Indultry.pd{.
43
Chapter
l:
Generul Consideration
37-
c€r6.fd, Sido!. ,yl:@ : r.tM ow Man lne.,ted o Cotot that Chansed th.
r,rid : W.1v. Nodon & Co., 200t.
38.
T. M. M.tt@s. Labqdtoty Manuat of
Wil€y & 506, 1909.
Mne
ard Te,lile Ch.milnr:
39.
htF://anicles-1lxritcctN.@rnlphysicG.hmicrt.dFcb_of_the.dycing,
40.
M. A. ead4 M. R. Ad't,i M.luood,
on Color str@slh of Ra.rjvc
society of Pa*xttu,?0w,
(,
..EffFt of vadoB
Drr Swifix 3R
-.
BufI6 dd Srll
JowtutolttE Chenicat
41.
,7-10.
htilJtuw.bdtand@@n/EBchakcdropidlT4g80/dyeA7?E3zRecliv€-
42.
K IJvEd,- Iadsttat
Iohn wilcy & Sons,
f.
31
Dtes: Chanlrtry, prcpanes, App[icatim. Dmsild.l :
2tx)j.
43.
D. R. W!dn& C.
,r4.
Plenlln?8s, t990.
M. R llorto4 Otsuic Ctunist.r.India: Do.ling KindeBely, 2011.
Hdls. Dn Ctedhr?
and
Appltc.tliM
o/Aa.
Ncw
yo*:
pp.
lt l2,lt l3
45.
46,
47.
48.
49.
D. R. Patel, N. S. parel, H. S.lai€I, K. C. pal.I.
"s)athsis,
ch.elerialion
DIB otr Vuioc Fib6." OrDi?a/
&d Applic.tion of Nov.l ra,ao R.scrivc
the Electohh Jooiat ofchekhn
, ZOLI, 3,
J, D.
Pct
r,
58.57
..Dycing
wirh R@rive Dyes:,, ryairy
Assciarion o{Tcxlile Chcnisi ud Colorist, t9El, 24-26.
htF//ss.uhredu.ptllesit\rours&Spdle2009/
H. zollihg.t. Colo Ch.rt /rrr. Swirzerttud &
wilcy-VcH CEbH & Cq 2003. p. 22t-240.
M.
E.Ilorie!
D. p.
Kre.kigl\R
Ma.lefon PIatu Mot alr.2002 46
E.Nonon.
cd,
cmary:
n
Jointly VHCA &
Co8emotiok a!
Ert*!r& Brorn
50. htrp://sbitrsfite.info,stainsFitddy€s/dye@lor.httr
51. htF://e!.wikip.di!.o4g/witvAqehren€.
52. http/$t.hr.du.pv@sitdcowshp.ing20og
p.iwr, A4qi6
R, hc. !p.
A
tot.
iiact,
Chapter
53.
l:
Genercl Considerction
hnp://ewv.t!8tulo6.cotdchdisay.homMtk-h.llchdistry-iradion/1h.ory-oft )B.atpx,
54.
55.
htp://w.ldl.reVariicla\rlDd10o/p.pcrridil05/idnl05.hrtn.
h[P/qw.Dpipoii@hps.it /docuais/alslsetni8rdold_BsisiMd
S20091B6ismimEruV-\tls.pif
56.
57.
hltp;//w.nigaors/docwnivDy.Malufictuing.pdf.
& N Shft,
G. T.
Mccnw-Hill,
198,1_ p. ?E4.
ANri.. ShEEs Cltbicat pm6s i!du.rri6. Ncryo*:
58.
J. Shorc. Colot@tt
59,
KrMv, By M. S. ,rSlwe hg Chemhtrtvith labtator/ BEe fieitt.tt
De i ; Phi L.aming rlt. Ltd. 2011.
60.
5r.
tttD/o.wikip€diaors/witychmophoc.
62.
Holnc, lan. Coloalion ofT.chicd Tcxlil6.
ad Asilioi.r Oryeic A.nisry And,4dication
Pro?.rrta M6ct sq, tX: Socicty of DyG ed Colouiei,2002.
&
Aspldd. rertil. bEing 4nd Cobatio,
T.xtile Chcrnht ed Colo&! 1997.
J.
il
Ahqi@ Assialion of
A. R Hotuts,
S. C. Anrnd.
I{dhdbook olTechaical Tsttles. Canbtidge: woodhdd Plblirhitrs
Lisil.d,
2000,pp.195.19?.
63. htF/rw.pbwhnevdycirs/fibenactiE.shtnl.
64. htt!/,i^wl.d)siar.@n/drsreudsniolc02.ch
65. hnp://onlinelibB.y.wil.y.@n/dovl0.llll/j.14?84408.2001.1b00
66.
P.
I
l2.xhhtii.t
BdAcB. "Ttc RcrEuahuirg of thc ColoMt M&ltractuing l!dNty."
Colord on T.chno1og,200\, 3l, l-14,
6?. D.
D.
Djrcdjwic,
'fternodyn
dis
of
N.
Djodj.vic,
R.!.tirc D}! Adlor?tiotr
Ashes no,n City H€ating
20tt,
Slojkovic,
Sidiot\" E@losical
M.
Sel@tovic.
Aq@u Solutio! o! thc
Ch.nttw ond Dnglwetins\.
&om
I E, 527-536,
6E.
P!.1<,
69.
Rljbb Singh.
Ji
ShoE, J. P@tlcol
.tad.ti.
Dpir&
Drar 56.d:
Scoiely
ofDycd rld Cobns! 2004 28.
Nw [|€bli; Milld Publiclriois,
2002.
45
Chapt$
70.
L K Dooi!'''@y.
OtSarh s'olhetk
l:
General Considerution
hgin e
2001. pp.1a0
71.
P.
S|)g!mji 'Thc D€iga Sy h€ir
R@lirc Dy6," Ph- D. Ttdn , Norrb
rd
Or&td
"&
Uli6ity
Pets,
Appliotioo of E sy w'5h ofr
Cloli
St!, UniKity,
R leish
2lxl4, pF 19
n?3.
F-L-C.Mil.x..
74.
Tlplcy, Dr Kelvi! N. R.lclivc Dy.3, Dcrdtn
75.
Uriv4ity oflieds, UK : Kdiator Dy. M@gas Vut!hop, 2003.
R- N. Sh@e, c. 1tustin Stueve's Cl|ntcd Procss kd#tter, MccnwHill,l98/, W.772-174
76.
77.
T.eil
Ptit&r8 So.i.ty ofDy.B &d
Colotis1s, 2n03,
Z2-273
hsp#Extilcl@.blogsFt.con20l2/01/dyciig{f-@tlo!-fabdeiilh-
!t
of ColN Chdishy,
http:/ dohouse.p2ricary/rfr1120379,bh,
hb:/tuw.iDdi@todil.joum.l.coifirricLc/PAd.trikrry?iG2631.
46
Chapter 2
Experimental Procedures PartSynthesis
1
Chapter 2: Experimental Procedures Pat- I, Synthesis
2.1
Celer.l ltrfoDtilotr
Chenicals us.d in Ois
rc*.rch so*
lre puhr$d liom M@k and Sig@-Al&ich
*hicl w!t! ofG. R. gmde ald u$d wirhour turthd rwificsrior. H-acid is otbined
toD Claiet Pakisl|n. ftin byd chrcnatogr.phy (TLC) ws carli.d out !!in8 F
254 /n !ili6 gel 60. Visible abolpli@ sFc!! w! n oid€d on a nmo llvVisible sp@tophob'nc1er. Ibe blea.h
6d DeMdz.d
frem Nal.ihbddi IndN1d6. Exialsl dycinS
To
uls piloled
ddutc Mh-f.slncs\ c@klsft* ed
Yud iGtrunent nodcl
ooh.n fdbric
on
$6
obbined
LR hb dycing Mclnne.
pcspiration vere pdfomed by F ng
no. s\Y-12 fo! ISO.COT, modd no. Y57l for ISO 105
ald YG63l for rSO 105/E04, EsFctil€ly. Light
6stna
h
Xl2
nist.d wilh l"lB lighl
fatdds lcstd by ISO 105-802 ncrlod. Colodm.tric drra of dy.d tubdca wE
mee5u.d on Data @lor InlenBtional SFclofhsh whjch b s.t on spcculd includ.d,
iUuiMt
D65, 10q $radad ob$ryd. Duing
ply wilh tai@
ndur.mcnt
mcaffidt
Reactiv€ dye smple! w€r.
rhe
re
f.bric is u$d to b. 4-
lo Cl.riant takistm to
cvdde lie percent puity of liMl pFducr The irsl m€nl urcd wB Shinda
HPLC 20 3.i$ with t,c el'tid soneEF ond PDA .lctelor E!41 mplc (25 nd of
wft
dissolved
i!
t00 mL of ac.toditdla vate! O:1) and sonicale for 5 binutes.
rh$. E !$d with pump A wi$ aceb rilc lnd pMp B eitb l0 DM
MnoniM ellle. Thcro ODS Hr?eBil colm w u!.d qith din. (m) 2s0 x
Mob e
4.6; penicle Bize 5r. Tot l flow kcpt al 0.7
2J.1
munin. r.enit3 w@ rcpon
d in
lh. c!d.
G...nl Etperln.nlrl
Aa dyd e
one of the host
@mon dyc @tqi.is, Thcy @ ain thc b8ic
{rucnE of At-N=N-Ar. Tb y appe! @loEd dw b h. tigh l4lof onju8ation
dal €ncompsss tuolgn N-N doubl€ bond to the aryl unil att!.h€d wifi n. In
Eilhe$is of ra dye plib.ry uift (R-NH' i5 @Dvcdd to ! diazoro@ sat sd
ilris is rcacLd wirh
eothd alyl uit,
41
\ napter z r.xpenneklat frcccanf?s rart.tynthests
2.l.t,lc.n.r.l
Pmc.dure for th. Sytrtiqh of Re.ctive DyB
'nrc starting
ucrial fd th. 3tarh*is ofchtdoridie rc.ctirc dy6 is rlE o(t.m.ty
rc!.tiw 2j,6-rticNoF-t,3,5.triazi!e (cyeuic chodde) 2. Th. fi81 scp is
cyanMlion of H-acid (8eindl-@phthol.3,6-disul_fonic acid)
subslitution
of (cy&uic chloride) 2
cyNic grid
twcd
3
fmi.s .y&uic H{id
with di@rirrn pli[).ly aremtic
l,
by nucl@philic
3. rn ihc ncxt st p
min s ButinS
in
drr
fonnadon 4 which is DCT dye. This si€p followcd by jhe addition ofbdd8iog
sroup
foi Oe fo@alion ofEqliEd hono-bifrerioMt MCT dye 5 (Scb.nct)
[l].
Sl.pr: Cy.llntioo
of
Cyeuic chlondc
@ol) wlr
t
tur
!
(10
o
pdiod of
H-r.ld
agiated in a@tone (50 nL) at
a
t mp.Fiw
below
mol) in aq@s
sodim cuboFtc $lmio! (20% w/v) $!l {En added in lcsa qwtity in lbod e
5
hou. A MuEli?rd solurio! of H{cid (10
hou!. Tlte pH was Daint.ined
slution (l% w,rv).
tho cl@ shdon
a1
pE 3-4 by @ncwnl addition of @diw ca$onate
0-j t for nlnhd I to 2 how
ch@ked by TLC etyer sysrcd ,-propdol; ErOAo
Ile @iion t|A els llinld
w
obtaincd
ar
H,o(6:1:3).
Ami'atic adinc (10
(10
mol)
mol) in l0 DL sder
diaadalion
sodim
is
nitiL
clFked
in 5N.HCI (2-5 nL)
t
pr @ld a10.5 "C, sodium
nitile
l'le4 ed sddcd dF! wi* ro minohy.trGchlo.ide,
by s1lrch iodide prpc., Cld slutioD is obt incd. ExN of
is
dcatrotrd by sulfmic &id.
StGp3: Coupllng Roctton
DiM
solutior
i!
Edded slowly ar 0-5
dlid, ptl adjusted to !6
t
6
pEp6red
sdih 6boEt
solution.
ro cye@t€d H-Acid sotutior
by 6dditio! of 20% aqueous
slulion is obtain d stir.d !t 0-5 t for l-2 h. C@pt.tion ofra.tion
*o! mritor.d by Trc. Solvcnr qBten +burrlot; Erhyt @tate: NEOH: pFidiE
(4:l:3:2)
Rcd @lor dy.
48
Chapter 2.
SLI{:
Addidor
Rs!..rirc
(5
n !dd.d dtop
Exwrinental Procedures Pat-1,
orDhrb. Br|l|ib!
Synthesis
Solralor
slllol) disbj!. hidsins solltioo ir
20
qi!. sill di'i!€. Icryd'rE r4| d
d
lc.rona or $t&r !us!.!!ioo
30a0 'C for 34 boulr pH
r.?.
M
Doditdld ty TLC. Solv.dt stst@ DBuhlol:
puified
Eityl ..rtat!: NH.OH: Prddi!., (4:l:3r2), Dy! stuliod b n.E &i.d
d! 5.6
ty bufrd elutim. R@tio!
a
(,v Visilt Sp.cdun !! rwd.d. Ilnbd! td
ryoi.d in T.blF3 sdd si|!l|r p.trrorc nc i/ift ounta ed p.r! oi ield
aoD
elone .nd DMr.
IR &
i3
i!
T.bl..-{ while IR i! mertion€d h r.sdl dd rliloulsior
Ity. ,lplidion io cltoo 6bric &d
frs*
p(oFtica rn|did. AI
iL de
colcc&d
Elortlil h lb T.U.. r-5 ofdrts r 3.
19
Chapta 2.
Blaedttttd Pncdnt PatJ, S]''da{b
!
R-NH2 Nd{q/Ho'
(ar) @|!dd..)
o9
R.N.NCl
Gtt I
#"
/.0-tr
@y.hdE)
A&ll+l
Nror
OlNr
e,{rodhotdr.rrdt!O.
)
S.[an}l
50
Chapter 2. Experimental Prccedurcs Pat-|, Synthesh
2.1.12
Sy!t[6ir
of Corpling
Codporott
sy,tt6n' oI't-(1,6-.li.ttotu4t J,uill&7t1.nbo)-rhldtuxynofi not nc2,7ditalJonb @a Gonpor"4 3)
2,4,6-Tric oc1,3,t-tiazim (O0l Dol.) is hlan
in
100
I
crushcd
ie
wilh 50
ri,
e.t@e thd
(0.01 nol.) +mir5-hydidy-naphthal.nc2,7-disultonic acid (HAcid) pFdisslvcd
150 nL qarer w!3 add.d, ncutilikd with 20% aqM6
in
sodiM @bolate solllion to pH 6, 3timd, k pt on icc blth
at 0-5
t.
o-, ""
* "'Y"Y"' -....._
t"o,'
.o,r" "E*
NaOrS
cl
SO3llo
2
schoc2
Syrlh.3is of Coupling
CobI.Mr
llidd
dye m srllt€iz.d in vlich thc forEtio! of 4{4,fticbloct l,3jltidin2-ylmilo!5-lydmry-EphrhrlcF2t-disulfonic &id is th. @mon sr.p in all.
2.r.risy
n6i!
In lhis slep six
.equircd
of Xri@tt4d
tlFs
mnatic
ald
olh6
of Nnatic
Min
conditios md in lhe
is alrnon
AroE lcADba
for
excess
13
.niB N
utilizld ro ge|Ei€ di@niM
dy6. Diazotiz3tion
t
id of
8i! eit! ra!i.[y udd nomal
of rcid, tha ratc of diazolizstion of
eili&, proluidile,
tue (S!beEr-}.
NH,
,A
r.-V
NiNo,
-'E---*
s.h€dd3 Di@tiztion
of
N=N
.4.r
*{/
Aronllic Amin (.-D
5l
Chaprct 2. E peanental Prccedurcs Pat.l, Synthetis
T.blFl: AnlDIic Anirc Ui.d i! SFdei!
or
Ra.riE Dyq
R
Rr_H
fu = solH
so.H
RJ =
sotH
so,H
&=Nor
Rr =
cHl
","-(-rF
M:
R.= cHr
2.1.2 Corpung
R.rcaloa for tb.
Di@ elutio! b !dd.d
uli6.
drep
wi$
For.tto!
of
sl G5 'C lo
cys@t
ADilochlorchi.rha ({.-df)
d g-Acid slurion
s prcpdd
by.dditid ot20% !qu@w rodiu ca(!ou& $turiotr
R€d old dyc &lutio! is obilircd strr.d at 0.5 t fd 1-2 h. Rc!.tid onplciid
Fonilorcd by TLC. Solv.nl s/slem ,-bltanol Erhyl ac€ratq NIIOH: plridinc
pH adjult d to 5-6
{4:l:3rD.
52
Lhapter 1. L.xtwinenlal Prccedurcs Pat-|. tnthesis
A'.N=N
N<o
qFA-I
OH
\cr
V-,At
N.ors,,%solt!
Di@liad amdc
!r!ic
Dyc (4.-{D
(d.-4t
Sch.mF4 Dye Fofution Reaior
A
I\H
HN-</ N
^r
(_)-rcNy'\.\
''
/\,\l\
N'O3S
\cl
-SOrNa
,'\
HOrS.
cl
lLorS
SO3N.
.D
tl
N-<
HrI-a-I
Ho,s<_>N=N/',l\ N_\cr
oH
/\,\l\
N.O]S
'SOrNs
Clnpter 2, Wdrnqnal
M"t
OH
Pot-|,
,A
l<
tqH
&".flt-t{*A \
N.olf,\o
}'I
l
Syttr,b
petin
Chapte, 2. E
113 syt.h6l
ntal
Pftce&-.t
Pat- I , Srathetis
olr.F(|uodlorott||!b.) (5.{)
AI dy6 e! srm.ticd.tord
t
T.Db-2: DimiD &itlgi!8
Diui.Fbdddlr
c.ord
|ilrilsdiriiat
idsiq
t21.
C.opo.d fti tL Srrih.rir ofrtFMCT DyB
(DA)
DASDA
!H
4.4LDi@imstilb.ne2-2,
-Disulphonic
A.id
II'N
IAl
H"N/v
55
Chaprc r 2 . E perinental Procedures Pat- l , Synthetis
2.8.r Slnt!.||,
of 5r,
ft,
5& 5E
Solulio! of 4',4'rn-diarni!ostilb6. (5 nM),
2,
disulphoiic @id in 20
6L s!l.r
sspecion is ad.lcd .lrop fi!. wirh 3tiring in a& ab, 4e, af b pEpor. 5., 5b, 59, 5h
dy.s, r.lpetircly. T.npenim L.pr d 30-40 'C fo. 3-4 boB. pH t ,t.t 5-6 by
cl
Itt
sorH
sorlt
"At
[.'J-1ur gu
HH)"
"=.1-Vi*i
Hoss
li'\:ftlFN{ )
sqH
3o3H
5.
lto.s
\l-
orH
'"tb*fu;'"$b
sorH sojH
HO'S
SorH
5b
56
Chapter 2. Expe fieual Prccedtea Pat-L, Wthcsis
3t
57
Chapter 2. Erperinental Procedurcs pat-j, Synthesis
2J.3.2 Sy.lbBtu of 5c, 5d, 5e, 5f, 5i md
SolutioE of
1,1PbdyLd. diuile
i! {4
(5
5t
nM) ii
20
Er s@bn tu.dd.d d'o!
wirc wir!
t
, a., ld !!d {f !o alt sf,, 5d, S., Sf. 5i ,id 5k drr!,
n pc.tivcv. TenFr.iur! tcpt.i 3G40 t for 34 ho$. pH Lpl ar 5{ by bIfr.r
diring
ac,
I|ors
cl
rA"
orl
E{-},]]
*1fi'""1J
Hoss+lF
so3H
,-
**$so"
sorH
sO3H
sorH
5d
5E
Chapter 2. F.xperinenal Prccelnet Pat-|. Syn h?*tr
fr
l{^N
I'
tr^N
9dT*r]
,'-o N*l*
tD{hNH
,ryffi
9"
ffi}*O
HO,S SqH
SOIH
SO'H
5c
ctd
r/r J.
SO--'f""tJ}'
",*{-},*#ff
M4*
-
V-HG*
59
Chqtet 2. qirf'ir*ntd Ptoctu?s Pot-l, Stttdttth
]'.\-
9l
"Y"rq,.-
cr
fI*"
60
Charter 2. Experinental Prcced,.es Pat-1. Synl'esis
2.r.2.4 syn
n6ir ol5\ 5l md 5l
iil
ri$ witlt
stiningin 4e,4d d{f !odlt 5h,5j &d 5l dy6, Fspe.tivcly. T.bF6te tept al
Sol io of U Pharylco. di.diE
3040
t
for
l-{
hours. pH kepl
(5
nM) in
20
,r 5{ by bullcr solutioD-
I'
fl
N^N
n,c-$r.
N^N
E{.'1
1""!}" s"
ilwffi#
N=roQcn,
orH
\?
sorH
^ l'"4'
solH
cJ
I- N
\'1
sosH
cl
N'- N
OH
F"!i"
r[l,-ns_NH Z\
\)
k--Jl
sosH
so+r
so3H
5l
sorH
N^N
u*
CA"l
sorH
sorH
5t
?9'
N^N
o,r@*'
lcelotu ir addd dDp
*N-Q
so3H
"o,
(hupv 2 r.xpninektal Prc..d rc" Parl. Synhe,is
'Itc st
e
ngth of dycs is
rmded
at room
m6uql
in aq@us solurion in quarrz
rcDp€Enuc in wrcr with
Tlble-3r Lmbda Md,
AbsrblM dd
*ll
(
l0
fn).
Spccia
ftcmo UV v'sibl.
Mol.r .ho.plivily ofsynr!*i2ld Dya.
Dr00" )
H,O
5b
5d
5f
(dro'M'
togt
543
0.954
3.23
29535.60
5U
0.867
4.6E
t8t25.64
4.21
519
0.552
7.78
7095.t2
3.85
521
t.2t4
6.23
t9,t86.36
4.29
523
0.32
8,64
3701.70
J,51
531
1.078
43.4
24E3.E7
t,l9
LlI
5.77
tn37.44
4.2E
5g
5[
529
0.824
t7.36
4145.51
3.66
5i
5.t
I
1.007
4.12
24411_15
4.39
532
0.%
5.51
t7422.E1
4.U
5t
520
0.E24
4746.54
t.58
5l
522
t.024
7.32
t39E9.071
4.15
556
o.9E7
1.25
4n3.529
4.37
62
Chopter
2 Exretine al Pn."dnrcs Par L
T.blc{: Eaic Infomtion
Synthesi.
of Synlhsiad Dye
Dv.
Yi.ld
Yr
Petorc l8-232E TC
ceHnctNlonsr.H
1546.37
70
rc
c$HrlclNriorosre.H
t106.49
1l
PaEton 17-2120 TC
c,
HrcuNsotrsd.H
t2E4.l0
68
Peton l&2133TC
c4HlcDNlotrs6.H
t284.rO
65
5e
Petone l5-t9l2TC
cdrrcDNror&.H
1155.97
60
5f
Pelon
16-16l0TC
Eqryti.d Apn@t
Petonc l&382E TC
c{Hsc,:Nr1oDs..H
1152.03
62
crH4cnNrozsiH
t574.42
67
Poton
l7-1623 TC
cxxJlcuNlotrsl.H
52.03
63
ldlonc l8l5l8TC
cr:HrcoN,p,.s4.H
Patticidn Purptc
Pdr@c 19,3022 TC
12t7.91
65
c{HlcrN
r60bs..H
t2li.97
70
5k
lelonc l6Jtl5TC
c{HncoNrODSrH
ll52.0l
60
5I
PdtoD. l7-1341 TC
c4H)G'NuODS..H
ll52.0l
@
crH{ciN!O!St.H
1574.42
15
5b
5g
lotonc
17-2625
I!!4r|ora'se
Peton. l9-l842 Tc)<
lEp !&t
ria
63
Chapter 2. E perinental Prccedwet Pat-1, Syn,hesis
2.2
IIPLC Prcfl. ol Dys
'Ihh nethod is suitrble for 0!. qualii.srive &d qwtitalire dalysis of dyB a il h.s
b€nd.$olutiod of dy€s, $tetiratio! .nd cprcducibtc E&nrion limes of s.paBrcd
6Dpon6ts t3l. Bcfor! H?r-C &rlrk &c risibtc rycFA E obrrin.d of sh
st nda.d dye io foud its bdidm a!&lb.E wvel.oglh (hw) &d i! ordd 10
dct minc iti r.tcnrion dm. d€ry dyc ws chos8lograrh€d epe6r.ly and pereived
{t
naiimm warclengu, All q!diF4l, q@ cadi.d out al rcom rdp.rlnr
(2F25 C) t4l. Ile p.il aM i6 c.tcut.r€{t by LC loldion $fige
lhrclgh *tjch dr
5l
peEalagc
oimi! dlr
i5
obrlilcd.
-10
15.0
FErB-rr HPIC ChroMlogm of5.
Chaptq 2. Expe nental Procedffes Pat-I,s{//,he:is
Flgun-2r HPLC Chtorubgm ofsb
FlgrG3: HPLC (xroorrogm! of 5c
65
ChAta
2,
l|!r!1:
Etwit&ttolMta
HI'LC
ft@dosu
P6-l,l'{,d'rth
ofsd
rNAU
2.
0.
tEra:
Ertc.!-.---
d5r
66
Chapler 2. Expeituentol Procedures Pat-|, S|nthesit
FlrnG6; HPrC chmmiogam of 5t
MAU
o+0.0
10.0
ItrF?:
tlPt
C
15.0
C}I.@!ros@ ofsr
20,0
mn
Chapler 2.
r:n
Itu*
Exrytnqtdl
Proc6dur"*
pot-|, St,i,th'/ttt
* HPL Chlddr,Eofg
HPL
.r*{ar-
o{{
o
C@er
Ewinatal Pnen6
2.
Pd-t , $,,drr,it
MAU
5.0
,10.0
1l
20.0min
r&r!.lo HI{c Cb@doSrm otsr
I|8lt..
:
gH.C
Cbodogne
of{
69
Chapter 2. Expe.inental Pmce.lures Pat-|, S!|./,thesis
rigurc-r2: HPLC Chmnarogrun
T.bL's: Puiry D.l!
5.
80.4
E5.6
wirh
Mri!
of56
!.rt AE wis
5b
99.1
5l
80.6t
95_9
5t
5T
66.6
88.4
N.D''
5l
5f
90.3
5r
5D
99.39
5b
I
5c
5d
^d
ft@ d* h i.rutlci{r
94.E6
ud
70
Chapter 2. Expefimental Pncedlres Pot1l, Synthesis
23
rl
rIIR Spean
{
rl
"$ {
J
E
t
I
E
>?
I
t6
;;
e
rl
7l
e. a r, P.,t
C-ae1 4 X*t.L.,s.l
a&4.,r.tb
#il
Gi
s
A
t
"]
i.
:*
r..dc: sbRdiaDF
----;*
Mmr.d, orlotlos d wsmrz
r-t'doi,.6r (.@)
3
a4.zr-A.J
tI
.l
i
rl
l\
'\/
C
l.I
,
!\
d\
,'it'i , fulir',
,i i$$i
ti
1
Lrd'
l.rn
t6lur'sa
dvscrcrt
xd$ha:.@1{edu)
:t
(hdatrnr)
ii,
i
)Lt
J. P
a.ct
64u.t+t.t*,
-
ab'
R
I
!r
ll
;
Brd6 : rd (hosrudD
x..Ed: rl/o.r@o'8:rl)M
r..dbrtm. r+r (rE)
a.
Ia.
*.
6.
Az
d.
c
I4--.t ).--t ,|r''-J a.l*' ;w
-
x
e:
E
t
!
i\
,!'
+dn
r.@Ed : .g/otsoeovrcrokz
IEtldm:a@r (t@)
:
t
(ho*ar6r)
€
p
F
!
t
t"
tl
E
tr d, i sl|.U d.c-q
lF-*i. * F5]r
H3"
F.*
F"r'-***-
,|'
!1
i'i
tu:m
ll
I
''.:
!|M|'&.rrd4'6dcd'
lll
lli
/i
\ .",
iii
iiit\r
t r ll/
-4,.1 i
I'
r,il
"
lii
llj
VI
I
s
q.
$
o
F
.l'
I
s
E'
^i;a
!d 16
'b
/)
s
E
!.,
i
,,'92
$
t
&
I
F
a.
o.o rs,
!o,
t !* ti rlbrdri.do'*
.*
-
r*&a
ki*
s
t
$
t.o.t
*, -.,4t
I
I
L
s
6
id
s
E
t
F
Ii
3
't|Elt^hr*r''.d.|*'
.4lh
^odit@k*
ytu94* zUbt
IE.
$r
$
t
v
$
e
,i9l
r E t
nn'r ri-r.r0--,
b,ir.r--h
.Fe
-
,
*Etd rrr'r
F
E
F.
.#\
ll
f
i
I
{
I
I
I
I
I
qI
i/
R]
T
ti
F
d
l.!5!
l
qa, sn
2'a
t- .!r rb rb. r-{a.rdardt
l':
rh
,'..jrh
'lnr
rtua- 2trt
i.-
I
E
t
F
Chapter 3
Experimentel Proccdures p srt-2
Applicttfun and Evaluaion
Chapter 3: Experimental Procedures pa.t-2
Application and Evaluarion
3,1
Go.r.l [lfom.tlon
Appli.alion of
dy.t
e
dF!
is
Bu![y
done by
applicd by a\lErEl dyci!8
d]ring Dcriod or
by
pilriry.
!r@s ed rho lhci,
In rhis snl(ly aU
arluatiotr is
sp4tophotometically .nd by ph)sical testing.
Iot
UE dycinc.
anci
n r6iz.d
tud bl.ach.d fabric wa! usld r! che.k fastlcs propcnic!
drling. fte liqrcr mrio was mirrain.d
l0rl duing dyei.s lnd it wls wshed
wilh non-ioric ddcrge .n ! @bplclioa of dyei!&
Ilc $lr conc, *r! @si$rr for
all .ly€s r?. 50 94. vhilc sd! w$ lsler s 20 g/1. Both
cberlcqb werc f€eded in
liquid fom in ncquot inr.d6lr. Th. fabric
nr
M
.t$ys w!!..t b.forc dy.ing. Drying
pllrc B odcd out ar rood! cnp. Sbp by sl!! dyc,ng @w {,ltn respet
to
rdp.nture ed tne h nedion below in the fm ofrigur.-r
lnd T.bh-l.
Dy.ing wa! casicd our on L R, dy.ing machin€ of
Ro&he. rnt. Touci eic€! contDl
sysi.m. Dyc q!.diry fo! r % sbdc is pre
disotr€d in rcquL.d mte!
dd
rh@ loa<te.t
gi200d[
sod!:609200nl
Sallr
37.5
83
Chapter 3.
Appl ic ation &
Frpeinentat Prccedwes pat,2,
B,aluatio"
Flgw
r: St.p by Sr+
TrbL-I:
DyctrU
SGp by Sr.p Dycins
pm..$
nA
*id dr
Rotrrion
Oycirg6
&
Cb;;
IlqAddirjd;iai
s€@nd
LiRr
Addirion-iai
Auatiffi
&!qnd Alktti fccdi
Derltrime
@l!as doql (.!d of
u
Chapter 3. Erpelinental Prcce&res Pat-2,
Appl icanon & Evaluation
AA.! thc conplction of dycitrg
pcedft,
rb.
f6ric sw.r.h6 wE snoled
iw
lh.
rin!.j in cold warer v.O? wcll th.n sajl smllh* of eioor,l soapiry M
lakcn ollt sd res of rhe fabdc sw.tchcs w.rc s&pcd-ofr sing non ionic dcr.rgenr
ar
dye
!ol5,
t
fd
mir
Tte absorbana rdu* ofl!.
8c90
l5
dycils tiqrd b.foE ,nd
!lo!s with E0etdce valEs of &ied, dyld faki.
M.uuren.
,fid
tb. dyci!8
wft
neasuFd
swarch.s b.forc and afrc. wish
rrbrtc Cotor Err.bglh
In color.qudion CIE L. a. b.coordiurd on
Dara Color Sp.crlolhoroDetlr SF-600
wil! .a iDt 8ldidg spheE r.r$ry sld a f.bric holdd
le.$ry uth rlc foloeing
scinnSr illMinqt D65, ta$c ar€. vjew' s!.cda.
inclutt.d ald CIE 1954
stlpplandd siodad (oto ob3cryd). To c$imr. lh. d€g!.
orcrE colo! indcx
v!lB, ocb selL k D*surld fow rin ! .r diffcMr fohic jrsa
Tt sEr08.
vale of @lor @ @rd.d ed &la obtaincd e
r!!gi.d j! Tlbt62.
3.3
of
85
Chapter 3. Expefinentat pncedures pat-2,
A pp I ication
& Elaluation
T.bl+2: Spefophoionctric
L'
5b
5d
v
4247
144.47
16.38
10.73
\6.17
0.3?85
0.247E
56.29
J2.27
-9.63
33.68
143.39
30.84
24.20
32,46
0_1524
0.2766
58,6
ll,4l
.1.91
3l.47 156,Q
26.60
29.83
0.3715
0.2962
52.59
42.09
-10,80
4t.45
345,6:
29.33
20.17
2E.95
0.3?
0_2621
0.{8
19.t6
t,44
45,12
40.92
4349
0.34EJ
0.1159
1922
8.94
16.03
32,4A
0.157.1
0.1206
2E.03
294,50
t4,19
13.08
27.50
0.2590
0.2JE9
t4_52
26.73
32.9n
30,0E
25.86
19.30
0 3997
o 3417
,l6,El
20.E8
306,38
I0,87
9.80
t?.38
02857
0.2575
21.31
319.00
9.78
8.16
t4.26
0.1017
0.2535
28.52
340.01
30.76
25-44
34.10
0.340E
0 2817
3t.48
1..]l
25.79
20.03
20.50
0.1E89
0.J020
8.81
8.47
17.03
0.256E
0.2469
57.91
3747
34 32
5I
x
-11,41
42.89
5k
c'
Obsdcr
40.91
6),62
5i
in D65. t0 D.B.
39,12
10.12
5h
vdB
5i.51
51.87
34.95
t9.t6
18.98
2,99
1t.62
22.44
12,3E
t1.59
26.80
3t.43
6.90
.t5_29
-9.75
1.82
-20,45
2t.59 288.U
86
Chapter 3. E perinental Prccedurcs Pat-2,
Appl ication & Evaluat ion
33
D.i.dhrtior
SFcflE
of
6cI
ol Colo. Strclgtt of Dy.bg
dyc is
d.al'.d ie
ihe
So|Itio!
enFta@ ulu6 of th€ dycd fahd.s
l@
ne6ulcd spccrrophotonotrically al thc lmd md the corespondbg color sr€ngrh
(VS) vdc ofrhc !.o!ls wrc cdcul.rcd lsirg Krbclh-MuDl .guti@:
K/s = 03L2
2R
whF
R- a
ft
d.ciDd tlciiotr of
thc
en cble oflh. d}td hbiic;
cocfrcio! $d
s - Th. sca4edng cemci.nr
K-
Amur
aberyrion
of .rduEtior
i! th. drio of
llie end of cxlBuslion io rhc
rhc
ioid lDour of d}!
.eout ofd)r prcst
pr.st i!
rhc
e
d@ !t
in the original bath befon rhe sarl
of the cxhaulrion proc.s. DegE of Extaunio! in r€ms of dhribution
cocmci.nl
md liq@r nrio is giva by lh. rcLdidship
(r/KtL
K
E- t1+
Exllnid
bath
o,ta)'L
K+L
of l% dFilg b c.tcut r.d by spctrophoroncric
b.for. rnd aftct dy.ir8 wiih
the
,Esrdnt
ot ofrh. dyc
folowins forlnttla
E7
Chaptet 3. E petinental Procedurcs Pat-2,
Application & Eval@tion
-QL:92 xl0o;= A!A2 x l0O
cl
At
Whft E b th. d€sF ofdy€ .xhaslion
YoE
CI,C2
elh.@ne
'rri@
lrom ihe dy! barh, in pert nl,
of drr b.foF
&d.n
..ry€io& Espetiwly
Al, A2 ae solution absolbm6 b€forc sld .nd dycin& Bp€ctivety,
'[re exhrusion pMBs t@d! to lhc nisntio. proc€$.
Foc.s of nistalion of
lh. .xhalst d dye is infl@c.d by th€ Dol@utd sia of the dyc its sp.lid pbfle
(Steic) ed ih. solubilizing g.oups
E sr Th. orher exr.nal racbrs would Flatc to
rdFntft, ucbiDe.y us.d ajd lhc packagc plofte &d dtritie, (i! @s. of
Thc
TrDtco: Ldbda Md. wittr
itr H:O
g,tl
^r
yo
Exlaunio!
@D)
(AD) Abr.
s41
0.050
0.954
0.t08
EE,68
522
0.080
0.8?6
0_l4l
81.90
st9
0.100
0.552
0,t24
77.50
527
0.0E0
1.2t4
o.341
71.9t
523
0,100
0.32
0.129
59.60
5f
530
0,500
|.078
0.37t
65.60
5g
553
0,091
Lll0
0,120
89.19
5h
529
0.200
0.824
fu%
5ii4
531
0.050
1.007
0.281
72.09
532
0,06?
0.96
0.t26
86.88
5k
520
0.1904
0.824
0,t89
17.06
5l
522
1.024
0,35E
65.04
0.9E7
0.133
86.52
5b
5d
556
0.06?0
E8
Chaptet 3. F,,pelinental Procedwes pat-2,
AWI icat ion & Evoluation
Thi! tcm indicate
Dye
rhe
p.ro€lragc of dy. @val€n{y bonded yit'r fibd.
fiuiion h calquk't€d s tolloml
%F- k? 2x100
KVSI
wldc Kl/Sl ed
K2A2 fprtsmt rhe color yield of ihe dyeiDg b.forc
ad
ancr
T&1.-1: XMa. of labric with ?elwr Fixarion
560
102
5b
540
1.05
2,15
77.U
5c
540
2.65
2.Q
75.47
5d
540
6,45
3,6
t5.E1
5i
5f
540
l.l
0.8
12.7
550
6,6
5.7E
8t.58
5t
560
5_5
4_5
81.82
5h
560
8.1
7.00
84.33
5l
565
8.0
5.7
71.25
5j
550
E.5
7.7
90.5
5k
550
7.9
5t
540
570
9.1
95.1
94.94
2.95
86.17
7.6
at.72
E9
Chapter 3. Eryerinehtal Prccedtres Pat-2,
A pplic at ion
& baluation
Colorr$he$ .ld T.!t M.thod!
3.6
Thc
Atndim
ed Colorist hs del)1!rolld rhc lcd
,1ll.
@lorfatnss 6
rclbrd@ of a @ieial to chalge in lry of it5 colo,
chaaclerisdcs, ro lraBfer ils @lotutG) lo adjsnr D6rcdals,
o! bo0\ d a resulr of
tlE expow of 0! manri.l 10 atry €nvimcor that nighr be .n@uxr€F<t
duidS rhe
pe€ssing, tesring, srong., or @ ofil|. D!rdid.,,
or, it h a fabric,3 abitiry k retsin
,b @lor dwing ir! prcjeded life cycle. Colorfsras pbpdri€s de of
nmeroN
Associarion of TodtL Ch@isls
rl?es thal nu$ be coBida.d
b d€livd
{r
Pt{E.$r nust knop ! f.bric,3 .nvisiocd 6d
thai wiu pbdu@ a
w
prcdEt of ior.nue Flfolll1,M
3.61 Prhciptd of Cotor
frlns
podlct [5].
F@6ing choi6
coNurn€r wirh a satisf.cloix
in
odq
r.,
hdt
(61.
T€lilg
As$mdt of ilc
malufactu€ lnd
dyed substdc P|odud for qualig $ais ar
Oc rime of its
nnish€s {irh tabonlory testr desigD.rl io
clssifv rhe tevel
Pcrfomm@ duins irs usge.
Thc
obj{tiw
a$s@r
cfer! obidlcd i! usu.Iy b!d. o i!. b.sis ofvisual
comp&isor of ile inbBit of &y chesc
in rhc alpd@e of rhe suDle wirh
calibn&d $rdad 8re), rrai.r
n.
Iftie cotrdtntio! ofhydrolyz.d reetiv. rty. j!
E fiutl hot rsh b6th is <0.003 e
11, lrainins or \ [iE gnoG in
U. flbric wilt b€ pF@rlrd l8]. h t@y @uFi6
sllldalds luvc b€o se1 fo! Bling fsrBs popeni6
seh 6 No -jn i .mdionat
Orgeiarion fd nlndndiarion.
ofdtc
90
Chaptet 3. E perinental Procedutes Pat-2,
Application & Eylluatiott
Dycing depth: I -0% o.w.t (lccording to rie
l.
qlish
of ttF fabdc)
Urlt FErttB
Daylight method: ISO t0t-802
Expos rbc r.sr
d
20
slEida
dong with ISO Bluc v@l
hoB (eom.ndcd
for r.adjve dy.s
efcM6
l-8 to
Xmn o$ l@!
comer.idly). 'Irt Ighr fasttEs nting
oompor<b to lhe nunbd ofth. Bl@ rcfdlno€ siowing r @ltrsr cqual to ihar of
thc ten
2,
sple
in *ldch
E
is
excdLnt
dd I
vcrt poo!.
is
Wahim falnes
Dy.d
splc
ir rEnlcd with fottowirg D.rhod io chet irs fasrrEs aspeialy duing
ISACO3
b€d
splc
Soap 5 g
aith odrifibd slrip i! subjwrld lo &c foUowiig soturior
/L, edim
carbonale
aniydbus 2
g /
ntio l:5O
Rie ad dry. EvsluG tba chrEc
srlten of
Sray
3.
sale
tu
u!.d in which
1
L.i
60
t
for !0 tninucs
,Ihe
in sbldc md nainin&
re!.cacnr poor .nd 5
FlBor
ir
tiquo.
dflg
d@lLnt.
Pffindtion
lso 105/n4
speciDo of
the iexrilc in @dacr with tbc adja@nt
fabri*
e
hcaicd for 30 ninutes
t*o dif.r.Dr solutios (&id pH 5.5 or .lt!li@ pH S) @Dt iniog h.isiidi!. ald
ddircd. Iltd pl&€d bct*m rqo ptat s uldd a p.sse of 12.5 t!a, and ptt i, !
in
&yine ovcn for 4
ioB
Anwud! heg lo dry i! wm air d
lndinM rl 60 iLg!. Cddstde Ass ri. cbe8. h iba& ud slainils of thc
adjacent lsbnc wirh srcy
at 37 dcgre C.
lcat
.
9l
Cha?ter
3 Experinehtal Prccedwes Par2
Lhisridilemonohydrochlodd.monohyd6t A.'E|L
50 gL
sodiMc oride
Sodiundihydlo8.nodhophosphat
d.hydrale
Lhislidioe Eonolydrcchlodde momhydlat
22S'I-
dL
0.5
5.0 eJL
Diediu
4.
Onhophosphat
5.0
CL
Pi!a8&-V!EU4s
Ihis test ir intcd.d to d.icdie th. $Nitivitv of @lored ldlil6 b peroxv
odpoudl lik Sodrd pd boBG ehich b I comon iDgrcdi.nt of colm@ial
4.25 EIL
2.0 EIL
'fte l.sr speimco
is
imds.d
in thc abov. liquor d 50
b
fo. 30 ninucs &.iN, dry
5.Y@l4rb!!s
15O105 E't
Ilis tesl m.lhod is ro detminc lhc Bistlocc of th. @lor of €Kil6 to imcsi@ ir
wbr. rvd speida od moltifibd ntip s adjamt hdtc.id in d.mimralit d Mlet'
pled it b plsLs qith prtsw of 12.5 k?& for 4 ho$ .t 3? 'C Thcd $ss lhe
ch4ge,
B!:bb!!g&6o!$leg
rso taSx-l2
6.
'Ihis lesl nethod is
1o
dct rntrnc lhc rcskt&c. of @lor of tertilca to rubbing ofl
staining o0!er nal€rials. Sp€cilnans of
li.
ed
tcxtiles io be tested de rubb€d wiL\ a dry
dd sith s w.t rubbitrg doth using ! c@k mdt.r' Rub tb dd fto
siraight along ! back l0 cm lonS lO tin6 in l0 s..ond! with a domqed fooe of
rubbins cloth
22N or 9N.
Tlc sibnling of tlF rubbitg cloth i! 8ss!.d wilh srcv sc.L
92
Chaptet 3. Experinental Procedures Pat-2,
Applicanon & baluation
Trbl65: Rc$na ofvadou
Isb*
PEFdas
ofDrs
Dv.
Wrt.r P.nDlr.tiotr
-.
.
-RuDo|ng
Ll8lt
.
10
I
4t5
4t5
3
2
5b
3
3
4t5
3
4
3
4t5
4t5
5d
5
6
5f
7
5g
8
9
ln
12
4t5
i
3
l0
I
u
I
12
5l
l3
WbF .
sLnds for shtle
4t5
3
4t5
4
4t5
4t5 3
4t5 A3
4t5 2t3
4t5 U3
4t5 2
4/5 3
4t5 3
I
5i
1t4
2t3
4t5
1t5
4t5
4t5
4t5
4t5
4ts
2 3
3 3
3 3
3 3
4 4
14
z7 u
4t5 3
4/5
2B
3
3
3
3
3
3
4/5
3t4
3t4
3t4
4t5 3t4
4/5
28
3
3
415 3t4
4t5
213
2
3
4t5
4t5
4t5
4t5 4
5 415
4t5 3
42
415
3t4
3
415 3
3
43
4 3t4
3
a3
y3
v1
3/4
43
43
4y3
4Zi
4 213
cie8.
93
Chapte/ 3. L\perii'entat ptocedures pat-2,
Applicanob & baluation
3,? 3D.QSPR An.ly!t!
Compuidional study ptays
e inlodrri
rcle ro dci@1 tlE binding
thc @lluloF by applying v&iou nethods iD
dations od r€c.ltoFliged
bencncial Ddho.lology
0r
utlia
i
hini6M
ure
of dy6 with
time shuctu.. Dye,fsbric
er&lions, both have
fo! th. pEdiction
sinile coD@ption, The nosl
of difi@lt lmFrtjes iniiiare from
nol€culr struciuat infomDtion kloM 4s three dbcBional q@ibrive
smctur. propeny relationshjp (3D-eSpR)
t9,l0l. 3D.eSpR ltudics de @rbjnly of
importe@
erdal
in diltse b@ches of ch.mhtry inctudng Dedicinat
chcmistry,
phm(eudclt chem'sfy ed drus di.@very I L | 21.
Tris phclie
q?e
l*ds b
[
clo* @marion berwco butt
prepcrties oI compouds
$t'ich prcvidcs coe.crion b.rw€h
tr
ed U.ir notecute strucilr€
nucoscotic ald
of mncr. ODe ih. hodcl he b.cn dev.loped
fi.n fi
pmperis ofuDlnoM compoud. A Dlin
sl.p
to build
of the
!
*l ofnoledd d*liptoB
mol*ut6. Upii[
QsPR ealysis [13-t8].
h
now a
rhe
rhe mr@scopic
@ !.
used
lroFrriq
b
foEcajr.
i! coNuucrirc rh.lD_eSpR mod.l i,
tb.t si8 ry lltirtio! h u. sfirchj.al propeni.s
widc range ofd6cripro6 hlve Dc! dfcdb€d
in 3D-
siudi* rwo difctur data se$ of Ed !@rirc
dy€s wilh rhe hctp of
CoMFA prorMl is s.d
pri@il,
[19].
rhc i @ctio. of diniMr d]rs
includilg rhe
qtrqdirc dlq *irh . elutoF f.bdc
is t @6ptq phrsr@hoical pl@ss
ruled
by spoitc felrut* .nd lqtur ofile
dyc nol@ule In CoMFA llc i mllrio.
of
dyecdlulosc is inftMc€d by veiou
facroE inctudirS eled.ost tic ed scrjc
fielc
ed ihe eaitabt. dp.riEotol dara Thc ain
of rhi! sildy i3 b {ievclop a
PtldidiE
CoMFA mo.bl ih{ @@laL thc absrttivity
of dy.s *i1h rE .jtdrio, of mlaule
3D-QSPR
94
Chapter 3. E pefinental Prcc?twes Pat-2,
lppl ic at ion & Evaluatk n
*w
rs
d.ade .nd c@idd s a nd!1 Eti!!l.
mlhod to urd.Ftald Ihc {rEnld EquiMois of oy pbp€.ty *i1b rh€ iniedctive
specic. Abeativiiy is rh. pbpeny rhd i! @rsidq for the cl)mr eo* wh'ch
nod.ling iool5
uscd
ova hn
denonsf.le how mEb $e dy.
.xhaustion (E) &d hish lixation
i
a@r witt rhe eltuloe fibq wjlh to* dyFborh
qte.
3.tl Conpli.tio!.I M.rtodoto!,
AI moleclle modcli4
ncrhodr tv.rc p.rfqn€d uing Sybyl 7.3 t20l on Cquie
lntel'>a@n Onq 3.0 cHz d@t coF ptu6M ming udd oDc. SuSe
Linu I1.0
dvitu''Mr lrilialy a[ fiFnfts
fisLd
i! T.bb{ Mt
buiti by rhe cl|€mdhw
I2ll dd dm .rL.ned inio @cpudins 3D ni)cn!.! ei0 rh.
hclD
ofrhc
T.Hc?
1221.
Figlc
2: Sr.@luat
Atiglrtmt of Alt R.d R@rirc
D.l,bse Atignnmi
l.dDt.!c.
Dyca by 0E
Mahod UsiEg thc Mon Actvc Con oud 6t
4
95
Clnptd
3.
bipein.ntal
Pmcedu.es Pat-2,
App lic ation & Eva lua I ion
T.bfc6. P''.st R.d Rdcdv€ Dyc Stdcnlg wit!
thc
Abe6$vi9 (DntMoucn X
r(l)
."
S.No.
D),e
^r",lt,,l.*A*
Briddog Moleq "DA"
3.47
-1
6d
5
Didid6tilb@+?2LdisulplDnic
4,4
429
-dianin.b@Milde
3J4
6t
7
6g
5.43
E
6n
5.81
9
6l
6.21
l0
6J
Dimi.6tilb@c2, 2'.disdphonic
5.49
It
6t
4,4'{ianin bo@dnidc
495
6l
632
4.67
11
Di6i.dlilbqF22'{isulphonic
2.95
96
Diuinslilb6e2, 2'{isubhonic
l5
t.85
t6
0.tl
t7
1.95
IE
037
t9
5r
l0
5g
2l
5[
047
5l
2,44
23
A
5L
25
5l
26
5m
0,25
t92
Dimift srilb@e2,2'{islnpbnic
t,
1,74
t,
0/1
tt
Dieinestilb@2, 2ldisulplFnic
97
T.bL-7: Acntd ed PEdictld Ab$rprivity ofR.d Ra.tirc Dy6 wilb R.sidud of
&.dic&d .Dlo.bhdtt
CoMIA
5b
by
Rsldul
5.46
-0.16
5.17
5.38
-0.01
4.29
4.18
0.11
3.74
3.4
0.07
6f
4.94
4.91
0.03
6E
543
5.66
-0.23
6h
5.81
5.E5
-l).04
6i
6.21
6.24
-0.01
6j
5.49
5.37
o.t2
6l
6.32
6,51
-0,19
4.67
4.35
0.x2
5.
295
2.52
0.43
5b
1.85
L95
4.1
0,?l
0.57
0.04
1.95
2.02
-0.07
0.x7
0.43
-0.06
025
0.31
-0.06
t.92
1,35
0.5?
0!7
0.75
.0rE
2.44
2,41
0.03
5k
0.41
1.08
-0.61
5l
t4
1.39
0.01
2.32
2.22
0,1
347
5.40
n,93
6k
4.95
4.37
0.58
5b
0.47
2.tE
-1,71
6d
5f
5i
98
Adlladofi
Chq*
& Eyaletlorl
3.
W*n
tal
Procdtttt
pot-2,
#"fuy
99
ldteio"
Clqter t. B4Erlnatal Procder5 Pd-2,
& Ewhtmr{,t
6c
lm
chqte
Adit:otfot& Eyflhd@r
3.
Werina
tdl
Ptoc.tu.t Pd-2,
t^$HR-
l0l
Chapter 3. E petinentat prccedwes pat-2,
Applicatio & Btaluation
6E
HorsocHrcH,-d8o
-Fo
.\
91
9t
o3;.",c*,,*to,"
o=f
.,\
V,"'\:I
t-^i*",V
*y')^i,;,1,_lni
rw"o
sorH sqH
1\
\-/
so!I|
sqH
toz
Chapter 3. Expeineital Prccedurct Pat-2,
Appl ic dtion & Eraluatiotl
no,so'rrcrr,,.fo
o\-"r""r"ote"
.\irfr
A
V n"*t:ll'
[]*
*
V
"r{&.
\
.iui'A_\fEN
"=N.r,
n
fi\,,
SorH iortr
SorH
6l
1\.HrCHfOSOsr{
6j
103
Chqte
,lrylraaliot & Evabdldt
3.
Watne$at procdlB
pat-2,
/H.CrUCOsqH
6t
HOTSOCHTCH2\
104
Chapter 3. Expelihental Prccedurcs Pat-2,
Appl ic ation & Eyaluttion
ort
Ho;/s
fl91
N^N
y-F"'l
[n^{
l-y'.l'itl-'H'6$r*^
d9 dr*r!4
SorH
3.72 Sel€ctto. of
cwnt
N^N
Ii..,.:NE OH
()
SOrH
\g
sorH
q"',
I
sorH
Moleuld
study d.sls wirh thc i*rJ
diflcrdr d.l! 3€r
re
Drri rd I| Ilir.ca
rhicl,cd fDD lb. tir.rdu.
G:r) c@Fuldr
rcpotud by rh. J Palwzhtdtc. r, ar (dyetods 6. to dn), ft€y slrlhBiEd nd
ra.livc drq @ d.rivstiyc of l@haE-hydMyuphthrl.fl.-3, ftisulphonic &id
123).
Itd$d II: fis
dat!
et r.len
pEscady
,Fth6iz.d drs.oNi$ of
mthd tbinen (r3) c.oqouds (h!l/i!g '5lhc
dy.{ods 5. 10 5D).
Data 9.t of t*lnty Bix corpoututs wjfi tlcn ab€or?tiviry
G) dD?not/@ i! r.!on d
in &. T.bl69. rbe *ldlio! of ih. r.i!i!c .!d r.st s.r! is bo!.d d tu&d
alprolch. Twaty-rhrcc (23) conpoundr w.G elered fof thc
tr@ @npoulds w.r. studied ud€.rbc 16!
'cr.
r"idry
ser and
Fsr of
105
Chapter 3. F,lpetinental Procedures Pal-2,
Appl ication & Evaluaton
3.7.3
Ih.
Drb!.t P.ep.r.tior
3D sLucnlB ofdy€s
,or tbe AligtrD.trt
vw
dnw vilb rlc h.lp of Sybyl,
?.3.
'I!.
gc@.tty of
sile Tipos
lhc @npo'llds w6 midnizcd by @njug.tc 8rNdicnr method
aU
force field
[24] wilh 1000 iimlion. cellei8d Huck€l [25], mlbcc [26] and MMFF9 t27l
chqge n€lhodt wrc utilizd fo. rbc crlculirio! .!d .pplicd rhw ch&96 o. lhe
whoL d.la$t by !0o1. chdsc utility ofth. OpclEyca Q@p& [28].
3.7.4
Slnctunl Aligrbeot
AliSMdl h otr ofthe d6t sigdifimr scP3 fo. CoMIA studics. The 3D sElcn@s
of ihe E&livc dyc hol@ulca veE sliencd aocordirg io ! suitable confomaiionil
ldplale itich show.d bighc. iDt€ractive abil'ty with lhc c.Uulos. h lhi! cdc lhd€
it no Fiviouly rclorr€d data tEilaue for rh.e twtir! dys *t!ch irdic!& rbe
higlc! lot ncy of rt uctutc wirhiD thc dahs.!. Th.rcfo€, his!€sr absorbivjty
conpoud *!3 coBidqed !s a t mpht noLcule. For O.
Fwrli!
3.7.5
@6rol|nd is
rhe dyc 6r
*tlicL
ls
highcsl
cwnt rcrk th. m6t
a!$rlrivily
6-32 dm3/rur,/6 x
CoDD.rdlv. Moleul.r lLld Alrlylb (CoMrA)) Sludy
M
Au @Dporllivc bol@ulsr fi.ld .D.lFi! (C0MFA) P9-321
perfom.d by uing
SYBYL 7-3. Conpoudr rse pls.ed al ihc 3D l.nie by followins defaulr etliis of
Drcedw with 2.0 A Eid slacitrs. A spr @bon aiod wilh +l ch&ge s
c6ploy.d to probc lhe s&ric Ca$dJo!6) ald .Lcro3lrtic (codolrbio fcld
CoMFA
cncryio. Ttu cutoff int!@tio.
ftrs/
+ !0 tclynol
M
!{pli.d on
both rhc
CoMFA
106
Chaptet 3. Erperinental Procedurcs Pat-2,
Appl ic at io n & Ey ahtat ion
nsc li.lds 8.ndtd auiomncdly sd sLd
An altclulrion factor of 0.1Mus.d
nelds-
3.25
P.r.l.l
The Paltial
nodel.
s
Tt
l,dl &u.E
kln
^r+st
de!.ndent vaiablc io
n
thod.
(PLS)
Squte, (PLS) re1hod ljscd
CoMFA dcsqiptors
by tb€ CoMIA-SID
sled
to
@nstlct dd validarc th. 3DQSIR
s! indcpcnddl
wiabls
dnd prcpeny value!
PLs. It is exprc$ing thd ab$rbtiyiry in tcms of limd
conbinatiom of thc CoMIA modcl gen Btcd B stdic dd cldrrosta& ncb.
'Ite llldiqnvc poLltbl of the CoMIA protocol
M
alrlyrid by 'ldv.- o!.-ouf'
(LOO)I331.
CFs-validaEd ladysis metho4 in
from lhe daia5ct
dd
*l
ch orc
@npoud is qclldcd syn@lically
iis pbp€ny pEdictcd usitrg the Do<lel dqived fmD the rcsl
re
of
sd rcdMs ihe
nois ldel. Tle cross-validaled v.lu€ o'? thai Esulted h nininal nMbq of
conpon@ts ed thc lo*€st slaDd{d eru of pFdictio! (SEP) $4, accQt d. 'I1r
B ri obt iFtl toD Uc l@vmst Iswld@ yi.lls u opri[d nMbd of
@mpomis (ONC) which b ryciar.d by th. m!-rdidrri@ PtS ddysir. Th. rts
die
cohpou4 Colunn lilt ring
noIles
resuls wE
s.l ai2,0 kcal/ nol for dalrsis
alalysis Epcald for thc
vdid.tiotr wilh the ONC
lhe end, the CoMFA
sraphically inlery€led by ft€ld codlibution m6ps
using the ficld twc
10
gct
lle
6nal no.lcl. At
"std.v,@ll'.
t07
Chaptet 3. Experinental Ptocedures Pat-2'
& Evalnt iot
Appl ic at ion
3.8
D.t rnlbrtlon
D.lcnb.tloo
of lb Yilm
Arilbhrobl.l & Atrtifurgd AclMty
t
l".toAltioicrobi.lAdlijty
All &st sshplca w@ $!ffied on Mucller-HinloD agr (@de CM033? Oxoid) fot
atltibactdi.l rcrivity br di$ di$Bio mclbod. For lhis pu!Fo*, sl€dle diss (6mm
dim.tcr) of lihd papq of &s1 @npoudr qw Fllored Am sbct solurion of
of
lottrg/ml for synrbdic @@pouft. Bri.fly,
o
coDpoun&
o a disc.
lod
@nlainils 10019 for sytth.tic
Tle Muelle.-llilton lgat Plalcs w.c seded wiih 2how old
SroM itr Mu€[d Ftinlon bre$ (Oxoid) uing st€lile colton swbs lh!
pepar.d dircs tr€F placed onlo the agar !!rfac* !t diff.@l positions ed Pla&s
test cultuic
wd
incubatcd al 37C' for 24
inlibiiioB
in
m.
ll'
Resutts
A disc l@ded qilh
D.tcob.ito! offt t rto Alr'rtulgtl
afiitulgai &iivity
above,
M
l0!l sildL
rccordcd by
DMSO
m
m6uing thc en. of
!$d d a @olrol.
Aca|rity
die diruio! D.rhod a d*iib.d
vortex in smdl $rcw capp€d lubes to ma}. a
ale detabired
fugal cultue vs
$!r
by lhc
honog.n.ols susposion. Sabouud's ddrro$ agd (SDA) plats weie $eded with
thb susFsion. St€dle filtd dises @DrsiDing l00Fs pd dhc ampl. of synthclic
@mpund sEle pbc€d oDto the sud@s at difleMi posirions. ?late! were incubated
ar
@m tcmp.ratu!€ fo.
inhibitioE in
m.
Dd.Dlo.tlon
ol
A
di$
I wet.
R6ulG wcrc @rd€d by
loaded with
st dlc DMSO
@
us.d
BauiiS
thc
brc of
a ! conull.
MirirrD blibitor] Co!e!ln.io! (MIC)
MIC {as d.tahined for lhos. compouds th6t shov.d saore @tivity
of inl'bnion / concotration
i! pd
in prclimirdy
et t
m
zorc
scFnins.
108
Chapter 3. hpetinental Proceturcs Pat-2,
Appli c ation
&
Eva luat ion
l.
K. HEsa,.
2.
1. Shoe. Colotdhtt ond ,4ailtuie! OrgMtc
3.
Pror.ri.r. Meche{.r, tX : s@i.ty ofDy.B dd Colouists, 2002.
H. Aen. ",Vavel Retive Dret 88ed ok ptrinldiw ond g,iNralke
Ihd6,iol Dttt: Ch.nixtt Prcperti*, Applicaion!. D..@dsl
,oh! wilcy & soc, 2003.
S)dr.d". M.Sc. drsis, Nonh
J. Rob€rt on, M.
cdere.
ExdniMtion of Fibis, 2d
Cetic
,,Othq
t
st
Malhods
A. cRc Pllss,
:
Cheittrt ond Application
Utrit@iry, Nortb C@lina. 2009.
of colo' Analysh", in iorrtuic
t999.
5.
blrp/ww.hunterlab.@h/appnor€yan04_O6.p.U
6.
!.
Sch^d^. Coloinen: Un.!.^tandine the Ci" S)d/r, Joh Wt€y &
S062007.
hnp://ww,rhes!.lin€_conr46rilgtlniog-pm..dE$3a_!@
8.
Holm., Ian. Coloiarion ofT.clbical Textiles.
A.
R. Homcks, S. C. Aned.
Eardb@k of Te.hnical 'Iextitq_ Cmbddgc : Voodh.ld pubtishins
Limird,
2000, pp, 196-197,
9.
ce, Y Li6s,
Xq y. yua H. Li. ..Tow!.d b€nd eSAR./eSpR
inodelingr s'mulbn@!! outtier dei.ction ed wiabte setd,otr
usnB
D.
Q.
ofno&l f€allB". Jouel oJcohpia-td..l Moteato
25, t-t4,20tt.
distributioa
10.
s. Pui, J. S. Chickos, V. J. Vet5h.
Dertgn,
."Thd{i!)lsio..t q@1ir{iv. sh!.rF
Poperry rcktiolship €D.eSpR) Dodcts for pEdiction of lh.modynMic
PmFnics of
ll.
po\rtloiindd biphdyli
(pCBs): Elrh.lpy of sublinlrio!.,.
Jowrul o! Chemicat Infomauon and Conptet Sciem.., 42.t09.1t6.2002.
A. R X.!trii2!y' DC FaE, pftuttin. .,The pEscnt utilig ed tutuE polcnrial
foi n dicinal €hmistry of esAxrQSpR wirh wholc mot.cul. d.sdipros,,.
Cwtetu Topics oJ Medi.iMl Chenknr.2. tt?t-t156.2002.
109
Chaprer 3. Expe.inental Ptucedurcr Par2,
Appl i cation & Evalrat ion
t2,
A. R, Katdtzly, U. Mata[ V,
S,
Lobeox M, Karchor "Stuclually div.Bc
qeftarivc struchFtr'rotc.ty ELtio
hip
oftlatioa
rcrevef physicar prorritics". Jouttul of Ch.mi.al
of lechnolo8icaUy
ltotMtiq
and
Conwtel
Sci%e,10, l-r8.2000.
B.
M.
Kelsoi, Moledltu des*iptqs ir gS,{i/oSPf. Witey-Ilrcr $ide Nar
York, NY,IJSAi 2000,
14.
x.
J, Yao, A.
P@y.,
J. P. Doucer, R. S.
Zl!n&
H.
f.
Ch.n, M. C. Liu Z. D.
F6. "coEpdntive study ofQSAR/QSPRcoftlario using suppon
v4ror n6chim, ndiat b6is tulction reEd nerwkr, ad lnltript. lilM
Eu, B. T.
GEBia
". Jotul ot chnkat ltMnh
dnd chtniet &i.rc.
2n04;44.1257)266.
t5.
M. K4koD, V. S. Loblnov, A.
& Klrirrly. "eu$iud.hdicd dsiplors
in QSAWQSPR stl|di6".
16.
Crert al Revi*;961t027-r(44. t996.
J. Devill.s., A. T. Bal.bd. .,Topologha! rdicc! ed Relatcd Dc$dlloB in
QSAR ad QSPR". Cordo' a'd Ar.a, S.i.er; N.w yorlq Ny, USA: pp.
2t-57. 1999.
t7.
S. FDlr-Timofei
c. Schlilrbm
',Compmiiw moleculd ffeld edlysis
(CoMFA) of Eidic ozo dydfibd rfrniti* r: Os.pbae noleda.
dbiid
dwiptors'. Joonal of Ch.ai.at InlotMtin an!! Con@tet ScteM..,42:7EE795.2002
18.
,. xl B. Glq B. Ch.!! Q. Zblag. .A eS?R istrnenl for rhe themrl
shliliri€ of s&oldodct NLO cl@moplDE tuicdns". Jtuna! of
Mo te c ul a I Mo.te I i, ga\2165 -7 5. 2OOs
19.
I. Iabira
Tii|of.i. "Cohp&tive noLcutd feld .n trsis (coWA)
ofdy.-fibrc .fr!iri6. P.rt 2. Srr@.kntJ bisraro nycs". Jottal of Mot dttu
W. M.
S.
t ttuct te : THEO C HE Mt3
20.
62:1
5 5
-r 62.
Sybyl T. 7.0; Trirbs Inc., 169 Souih Ea.l€y Rd,
usl"
St Loui!, Missui
63144,
19,6.
110
Chaptet 3. E pemnental Prcce.tures Pat-2,
Appl icat ion & Eval uotion
21.
UltrCD.6.0aDdCb€m3D
tltlMtrv.c|mhidg.soi.con/sftwrdchcndrlw,
2001,
22,
23.
O Bab.l.
J.
Th. opo eucc chdisiry toolbox,
PalNtiwicz,
E.
Mltjs,
K. Blus.
w,ot€!ba!€l.org.
"Died Tettfuclional
Rc!4tive R.d
DlGs". Fibrct & Tenils in Estqn haopztl0t6+67.2002
24.
M. CleL, R. D. C|:@., v. Opd.nbdch . "Validalion of $e
Tripos
52 fo@ ficrd". .rorel of
8tunl
PutPosc
Conputatior4l chenistty,l0,982'1012,
I989.
25.
K. C. Tei, Y. C. Ch€D N. r{.
ttiro,
C. L.
w'!s,
C.
L
Li!, Y C.
la,
M
Li, B. wang. 'A conpa.hon of diflcr.nl cl@ttosbtic potenlids on Pr.dicion
islmy
C h e n t$ t
25.
in CoMFA md CoMSIA Ettdies". EutoPeon
!
i45 : | 544-1 5s
Joswl
of Medtctrdl
t. 2010.
A. Jak.lid , D. B. J&k, C. L Bayly.
"rd, .iicient
gdenlion of his! qudity
atonic chdg6. AMI BCC mod.l IL P'@Gletiutior
ed v.li&lid".
Jow n4l of Conputatiord Ch. n tt trr,23tl 623 - | 64 l. 2W2.
27.
28.
Eoleuld force 6.1d. V. ExLsior ofMMIT94 Bins
cxperiinentd .tai4 additio$l c.nptaiional dt!, &d enPiric.l rulcs"
Jo w ra I oI Co npdtat io tuI C he nl"/,il?:6 16-64 l. 1996.
QUACPAC. Olen€ye sicnlific sfiw.re, lnc,, vqsion 1.3.1,; Sanla le, NM,
T. A. Halsr.n. "M@k
USA 1rw..ye!opa.@m
29.
200E.
R Uddin. "Colv$A &d CoMSIASD{SARond}sis
o! hy&omic &id deilltive $ !t!@ irhibito6". Jomi o/ &d/t.
Z. Ul-Hag A. Wad@d,
Inhl bh to n atd Medic ind Ctu nh!ry 2W9 24t27 2-n 8.
l
Chapter 3. Experinehtal Procedurcs Pat-2,
Appl ication &
30,
Y.
baluat ioh
Lv, C. Yin , H. Liu , Z.
h.Ulivar of
POPg
uirs
li,
CoMFA
Sqa"cer. A|i}E20:t{33-143E.
.lL
^A
Cor,tsa^'.
I. Glrci4 Y, Fall, G. oonca" QSAR, Dooki!&
ifi bito$. CUE@I Phr8eutic.l
12.
Y. w'ng. '3DQSAR lludy on Bitrosdqic
K I{. Kin. c. c'!co.
JNMI
dd
of E
ettoMrtal
CoMFA sludilr of GSKI
D.tnC', 20r0i1 61266-261 5.
E. N@llino.
'A dlicd Eviq of Ec.rn coMIA
applicatioN. PcBpectircr in Drug Dilcov€.y ed De.igD'. r98il2:257-315.
R D. Cnll r, D. E. Pdaloo, J. D. aunce. "ComDditiE d|ol.crll& fdd
dEllsb (CoMlA) l. Effcct of rbrp. on birdirg of 3t roi.! to @id
ptollioa", JowMt oj.{mqt@n chemktl So.iety l988irl0t595r5%7
.
u2
Chapter 4
Result & Discussion
Chapter 4: Result & Discussion
'rhis chapLr dcscdbB 6ults &d rh.i. pssiblc cxplaMton up ro ihc prereDl
ho*l€dg. ldtlining ro lh€ sr!ftesis, .ppliclrion dd .valurjon of f.sticss of lhc
ta4eicd dy6. 'nE rhiia! Dr(no!@htobaisift) dyes w@ synrhciirld qhich
@nlain dift rnr subdtiM?d aryl min$ .l diazo @BFletrt and a bddging grcup
joilioe tvo dy+holaule of di+tlorcrddinc.
'Ihe seleciion of rc&tive greup govem! dyc ch$acre.islica such
liber bond s||bilily,
od .frci@y
3 @EAtd
dcpodert o. th. cbrcoopboF
n.y Bulr
$bcl.ltivity
in
Esctivily, dye-
Ntauld
of rc.orioi wirh the fibs,
phlsicsl chcnisfy, stcrcochdislry, suhBtanrivity
s
siructue
ad afrnity_ Sut6r6ririq b norc
!o rlE Ba.rirc srsi.o. A hield dye
cs
a lowr dy.,$llbitiry ehict ir ou
is
ircEs.d by
additio! of sllphonic acid bd it f.vos dycing by havinS hidet !.iEary .rlFusrion, a
higler t€action ntc for a givd re&tviiy, a
loftr di6sion
coefrici€nl, a hisl€r
.fftci€ncy of nxaiion, lcs eBitiviry ofdye ro nh. vdialion in Plocding condirions
sucn 6 t npcrahtr. ard pH. Suht ltivity is thc b.slE6e of th. capability ofa
imture
rticl
obw.d in lBdr pmjccl. Covdilg
powr G b.st wh6 tbe substartivity is.irhd rcry low d hjgh_ AltDugh d ir{,!@
dye to @vcr
or d.ad fiben
in tbe dr! sbstdrivity
tur
is
be @tuollcd .xrctully by lowsins of the dyc
€olchtntion, by using hidd colcdiration of d..rolrre,
pH (up to
I
l)
and lower
liq@! to eood! rario. Rcactiviry of
alt€dns thc pH or lempenhr,
loE cnpcntw, hider
a dye
cm b. nodifi€d by
By a suibbte sdjustbor of pH od
i.Dpdate, two dy.s of intrisi€Uy diflant Eactivity may be nDdc ro rcld at s
simil& 6c, Dtq of pr*nl wr! d b8.d on s-triuin @riv. gDup wnich hlvc
good va far!|* pop.nis in illnlin. mcdiu ed tbe subBtdlivity is towrcd
i&indly by bulkjness ofnolecde de !o $tich wlshing pbFrries arc inprowd. It
k
also found in ow
peBpitalion
6d
ce
lhat
peFbcate
e
s
o!
moM
borh,
orctiaziDc hay. fajr
fasl!.s to lidr,
@mp@ to oth.r rcrciive dys in
6e
sood to
ofrcds,
pFFnid i!t!nd.d primeily
for exlaust dlrinS. All dya stEtuB d. st1mchic.l ltour 1[c aoirlt tintilg
didi@ ed all of lhc6 @nr!b rd notE@ chromosm ar @h dd of ih. nob'ne,
th.e bifilrction t dy. noler{B e .ppoxinately teie rhe sia of daloeou
Thc t rg€i.d dycs
designed to
nonofrmdoml .trucnfts.
schidc bcrd fas:tr6s
Chapter 4.
Thei. noderate
dy.ins
1o
bish substantivity
tcnp.nnr
of E0
g
€l]sw
ex@Uent
Res t & Discrssioa
dhawtion
valB ofsbour
L&titrg ro fixalion
a1
the pEf€ned
?G80e,6, although
in
full deplhs lyphal neEb.u of the msc my rcquirc Ball @n@nralions s high 6
100 g/L for oFnral yicld. gigh-i.bp6atu! .ppli€tion 6ndiIio6 c6e sood
lry.lins {td thc high fixalioo to& to b.tb uritization ofde dyc! alplied \rirh
hydtolysis
ed
ls
@londo of
Bult in & opaire-up of
@llulose hydbxyls,
less
th€ €mllcnr. By tlisins the lnnpetalue sc.ns to
thc @lluloe rt
stue, ilc@ing
€nldcing th. re&liliry
h<l ovenonile thc .cdvation
as welt ar rbe
r 6c
of
ecs
10
Dobiliry of dyc molecules
.las| bMid of thc dy.in! mMa, tb*by
inc6ilg 0t lael ofmoleclls activily otlhe dyetbor s/sten as w€I s dyefibct
iltqr.tior 1lic lu@hrcmes colfcF rhc s.li-foming @p&ity o! rhc @m!oud.
ft.
vdy huch !.t ogcn@B in strun{. due to which lh.
Mutuy in ncswtucnr is hist y !r@Ed. MoMltr, fadoE tike siz€ of smpte in
ill.86titrg sphaE, diEcrioMl sltucnlF duc ro @E qtilc t!).asilg in difq.Dt
rexiile $mples ar!
hdspaMcy of s . dccEes thd accuacy of ncasLjEnents_ Sdlt by
ott@DiDg O.r factoE by n*eing lhc tuplq ia p&deid.d dnetor sturs
dircclions,
ed
backidg i1 by irs
oir! thr.. fotd
s
ihese e..oB
ir0ucdcjrs id compeilon shrdia of @tor Mich
colos
Elal
i
bsuc
!o hrc, Chroda lDd
tishh€s.
.Dsig of th. srnthdsia dy6 incl.{$s du lo two dyc@t@ul.s joired
togcrha. Th.y behavcd .x@llmr sotubitity ln var€r duc
ro bcE.!.d !Mb.r of SOr
srcupq *ttich in tum
e
P.lhap
difre *ily
ln. tibcr b sis bcrs Eigdtior and t*[r8.
incrcse in dyc slubility nay b. !frarcd €xtdully by inc@ing fie
t nP.@turc, addiaS
le
iD
lrd dLtBilg
rh.
ui.
of .l@botyt4. As
!t!gl
dycs
qd
r nucleophilic displlcemenr m.chdisn lhowcd a good srabitity !o alkati
s!d. ro
difi.&Dt .legEcs, tss stabitig io acid. TI|c N of ! Factivc d)€
@nrainirg rs
by
c..rf.
ercupr
ptu6$s th.
cotrBpondi!8 fxation cffici@cy Lvcb
ed
e
abolt 75%
95yq rcspe.riv.ly. The shade of rhe dyc wiih rclsrion 10
di@ 6nponot ed
hidgjrg gloup sMjcd. nihcr rhln iG ,!!toge wir! otrly ore ucriE grlp p.r
molc.ule irc&$es ihc fixatio! from a g?icct 60% ro approximately
80/o on
av.Eg. i! a{lust dycin& h pad-bdrcl Shrd. ofthc dy. sbin.d t@
!.d ro Eddth
e
bluc tonc
a ob6F€d
by l,
nd
540 nD ro 5?O
m
on rhe fsbric by UV_VIS
s!.ctB
6
ll4
Chapter
BhoM
4
Rcsult.t Disc,s\ion
i!
valB
T.bl.-4 of drpld 3. X tm i! nn snd d)r exhusrioi studied ty I(/Setile dr! fqarion b cdqlrt d by l!flcq&e De3sl|@crl of dy€d htric.
!relcni.s of5i 10 5n e rc@rdcd in T.bt65 of.hlpra 3. € (epsilon
valu.9 e Emded in T.blF3 ofchalte. 2, s!4rophotometd valus &d Lr a. b..
valucs&ondalacolo.t@rdcdioT.bl62ofchapbr3fondat color.
Thc farhss
ln additjoD to ini!!@i!8 solubiliry, luxocbmncs sEh .s SOr sdphoric eid e
.tr .tir! dlg $bslituda in previdilg rrgd c.los. 'fte yicld of all dy6 is good &d
&Ddhli
he s in r.as.d moleds mss giv. inc@d yield.
Dy.5.r
t!.
wF n rsuEd h
! hsco A-30 spc.trophoromrer ed
following FlIs ob6.ded. IK &$.r'cr!): os 3{44 ({II), 3100 (,Nn_), 1616
C
IR specta
KBr on
N=N.), 1587 CC=C, Ar), l42E GC-N, glrieinyt rine), 1369 (-S,O), 1209 (SO),
?59(-C-C0.
Dy.5b:
Tltc IR
sr€fa wF n sucd i! KBr o!
&UowinS pqks
obi.dd.
IR(
a
J.9
A-30 stccblhotometer ald
Jaec'/cD''):D* 3444(ort,162l CN=N,),1558
c=C' Ar), l43l CC-N, sridinyl ring), I l9t (-S-O), lO42 (-S-O), ?90 (-C-Cl).
The IR spectF w.F ncasuEd in KBr on a Js@ A-30 spcctrophotometd
fouwi's p..b obsrcd.
C=C- Ar), 1429
rR(
J!sc./o.'):D*
(_
dd
3441 (,NH,), 1621 (-N=N-), 1596 (-
(-c-N etdlziryl dnd, I32? (-S-O), I120 (-S-O),
?92
Cc4l)_
Dy.5c:
Tha IR spdIrs
wrc neasud u KBr
fouowins pe.ks obserrcd. IR( Ja$..,/mi)r
C{-
Ar), l4o/l (-c-N,
rrrieilyl
on a
o*
Is@ A-30
3435
(orl),
spe.rropholomter
od
1626 (-N=N_), 1556
(.
dns), r 188 (-S-O), 1043 (-S-O), ?90 (_GCD.
Dy.5d:
IR
nr. lR
sp4ira were mcasu€d
foUowing
H-
Ar),
h
KBr om Ja!@ A-30 spcctmpholom.t$ od
pets ob*r!d. IR( J4sc./on r)rDd, 1441(_NH_), t62l (-N=N,),159j (1429 Gc-N,
!-tri&jryl rids),
t
32?
(-S=o), I l2o
(-so),
792 (_c_cD.
lt5
Chapter 4. Result
-Iae
& Dl'ct6sion
IR s!@t! wrc nasulld in KAr on a
Jas
A-30 sperlqhoroDeter
!d
3491
({H),
33?6 (-NH-), 1618 (-
nnd, l40l
GS=O), 1189 (-S-O),
followiag!ql6 ob*ftd. IR( Jsc./cbi):
N=N),
1564
(-c-C- Ar),
1444 CGN, !-triazinyl
ed
712(-C.Ct).
The IR spectra w.re m6o@d in KBr on s Js!.o A-30 lpcctropboromeio
rouowing peats obsen€d. IR(
JMo/cnr)rDn(
ed
3442 CoH), 3l 13 (-N'n-), 1622 C
N=N'), 1562 (-C=C- Ar), 1406 (-S=O), 1184 GS-O),773 GC-CD.
DJ.5gl
The IR
s!et! ll@ m6u€d
fouowine peats
N=N-), 1552
obwd.
(€-
in KBr oM Jsco A-30 sFctrolhotoneier
IR( J!$.r'cmr):
o*
3429
(-OH), 3395 GNH,),
aDd
1620
(-
Ar), 1400 GC-N, erisrisyl ing), lt92 CS{), 1045 (-s-o),
n0gaat).
Dy.5h:
!
fonowile ?ealc ob5wad. lR( ,ec.,?cn ): D*
The IR
slet a rry4 he3uld in KB. o!
c=c. Al),
1404
cc-N, siri&byl rirg),
I | 84
J$.o A-30 sp*trolhotoneter ud
3420
CNH).
1622 (-N=N-), 1558 C
(-S=O), lo40 cs-o), 815 (-c-cl).
Dye5ll
IR
Th. IR sp4ln werc m.Nuled in KB! ona
following peal$ observcd. lR( Jasca'/cn'):
c=c-A!),
Dye
Iso
U.!
A-30 s!.crlophotomerer
ed
3439CNH), 1520(,N=N-), 159(.
1339(-s=O), I | 98cs.o), 7?0(-c-cD.
5jl
IR
Th. IR s?eta
l@ h*utld b
KBr on a Js@ A-30 s!@rophotone&. @d
followils p€rs oheded. IR( Js.c,/cri):
H-
Ar),
11146
!*
3427 CNH), 1620 cN=N,), 15a9 C
(-C-N er.idinyt d,8), I194 (-s=o),
1042
(-s{),
?66 (-c_cl).
lt6
Chapter 4. Result
& Discutsiok
Dy.skl
IR
'[re IR spccba 9@ nc$uEd
p.lb obwen.
fonowin8
c=c" Ar),
1406
cs=o),
Iss/oD )rDN
IR(
1045
s K& dis o. r Jas
Cs-o),
A-30 spehoptoioncr.r sld
343? (-NH-), 1618 (-N=N-), ls54 (-
?9cc.cl).
Dy.5l:
rR
TIE IR spe.tz wd€ m8u€d in KBr ona Ja!.o A-30 sp€Eopholonctcr lnd
JM/cm ): od 142? (-NH-), 1620 (-N=Nr, l55l (At), | 396 (-C-N, sr.ieilyl ring), 1 194 (-S=o), 1043 (-S-O), ?91 (-c.cl).
following pdk3 obsw.d. IR(
c{IR
lte
IR spotn w€r n.$u!.d
i!
KBr oE Ja|co A-30 sFcrrcphotonercl ad
fouo*irg p.{k o!*n!d. IR(
N=N-), l4E7 (-C=G
JedcBr):D"- 3435 (_OrD, t622 (_NH-), l59l C
Ar), 1404 (-C-\ s-rieioyl rins), l2n (.S{), 104? CS-O),
170(-C-Ct).
Sp€cinl Pmpcrtl* of Dy.t
'Ihe
wrelogth of !BiDM
rd i.
&on 5r'5u
e
Mrd.d 6d p*nt€d
and appli@lion on fabic
0b0o!t€@ of
a[ stnrh.siz.d drs in edd
in T.btF3 of c[s9rcr 3 whil.
L-
of the$
T.bt.4 of chsptd 3. In pFsdt siudies
$!th.ric dyca 3 Oe coupling asd i! wc h alt dy6 {,tich i5 cyeuLd H-acid
mw dE diff.@@ in Ld e dE b difreFd di@ gtolps i! @Dbirrlio. wirh
bridgitrg 8touF. The rdtca of log 6 (notor .xlilcrio! @mcidt) $e wiz.d in
T.bl63 ofchlplq 2. Dy* with
bddging grcsp DASDA h!v. valucs itr thc m8. of4.274.4? los d, wbich shows
lh* dy.r h.w hyperchrnic efal o. hign in&ciry of llsorFion. 1,3-pl&nylc!,c
dyes
is prcsaled in
didi& sho*B good dcrildiv. wiq Bp6r b ab6orption ,tit. l.+ph.nylerc
didin ha l6s absdlion ta ht?ochrcmic .fro1€xccpt onc whic! hds u-Mi@
sulphonic
eid s diuo@bpo@nct
L abour 522
Dye 5r tds
l,ut
abour 543
m i! ercr. H@ rb. ilroducrion of 3ulp[odic
m lhiL
sloup
"
5b
hs
l...
-" *rui ii
Chapter
diazl).@F@nt qith DASDA bridging
prod@ hr"sochmic
crd
d*ltes
ed 3hinbg of lid $luc
M
Resuh
&
Discussion
lhc uv.lcagrb, dy6 5r
l{ow€vq, tbe iDloducrion of diazMbrondl wiih
.trd
L
up to 20
@
l,+!hdylcr.
is
dd
5b
o!6wed.
diadine btidgirg
ed 5.. The additioD of CIl3 at
e/a position id dieotupo!.nt in th. dyc 5. give! 5b with DASDA bndging
shows bad@bDmic etr c1 wilh iM*. in 13 nm of
in Mta, while addili@ of
^.!
CHr al pala positioD Bhows ts0Mbmrnic efiect wirh shift of l0 M. Anons fow
s!o*s b?@trcEic
isond
or
lEseit dy.s.
up ro only 4
in dy6 5.
dd 5l have hiehd 1,-" with
ooe ison of 5D ed 5g sho{s
5c md 5d, 5f and 5& 5h
subnftuelt al p4ra Fsilion then a uelr. Only
yith othd Fop.rtic!. Dy6 wiih DASDA bddging hiv€
ttu lioo 522 10 570, ^nr
eith l,3-ph.nyld. dimin. bddging shows Lq fim 540 to
appbximlely siDile
560
lld
b.idgirg wilh l,+ph.nylo.
Eldhon withdrailc
.ff*l
Oq)
didi!.
geups plac.d
n,
fr@
540 to 565 on fatsic.
ir @rjus4io! provid.
whici ir visible ir drq 5. ed 5l in yhjch
Wiih Es!.ct to fixaii@ p@dllgc
Lj
hrv.
ld
of faldc
a bath@hrmic
ilcEaed wirh
15
@.
5k show 95% fxation pnich is higbly
favoEue in @lo! pFdiction of rhldes $dich
ir
tum hvoE FTR
(fisl
time riclD
p!@sing. wlile di8znnpoidt of toluidinc virb dl bndgirg @mpo@!t sbow
!l@ lho
80ol0
6xation showirg favorablc gmup
$ a di''o{olrpoftn1
fo. fo@tiotr
dd c.llulorc. In dye 5J pnitto aoilile giv€ good
9lolo witr 1,3-phenyl.nc diminc lho wi& l,4,phdylene
of @valdl bonding betw€n dye
f$tres
p@
age
a
dimine in dye 5i which is 7l %.
'Il'is fel is dso appee in dy€ 5r in which 4iline ,s I dieo{ompoDat with DASDA
bridsiry give 95.I % fixliiod sltilc vith l,4.phenylonc dimin€ in dye 5. shows 73%
! bis dDp. I,4-phmylene dimirc
show exeuat fast!.$ with r-t.luidin
wh'ch h
w}lib wilh oihd di@@npoMt shoe!
Subhonic gbup additio!
lhs 5r *iicb ha .o
bddging with, out of six
i..
?5 or
i! di@nponcnr
95%
l$
&d lho with ptoluidine
86%
pct@taga
3hovs !o o!
sulplonic 8mp 3inilnly in
di@nponent
dr
lN
fxarioE
i! dy6 eA
5b
5d th.n 5..
lt8
Chapter 4. Result & Discltssion
Fuln.s of Re.ctlv. Dys
Th. f&ba thar alfet $e fastd.sr of Mcrilc dy6 &! th. cbFDopho.e goup, iLe
stability oJ th€ dyc-0b.r bold ed the @mDleld* oI thc tlmral of lbe utxrd
rsh*s
dye.
pDpdiies Esulti orc rcro.rd
i!
Trbtas of ctaplel 3.
h mhing
fash.s of sll thc de.ivanvc! fron 5a.5n e evaluat€d s .xc€ltcnt in shadc chsg€
wbil. siainiry is f!ir. In peroxidc sshing borh shad6 chrig. snd stljning e good
showing resisradc. !o onddjon_ Whctld
F6pi6tioD lad wel Nbbi!! f.sbess e
fdir 1o good wlilc dry rubbing fashs is e)(cett nr Lighi fisbrcls
of 5d is ex@I.ni;
e
5. md
5e
QSPR
Stldy
good whjl. oilEB
Frcn th. litcroiw
ed
foud
good.
sw.y it is quite cl@
riDt 3D_eSpR pE{rici.d ! Elialt. dodcl
*hich could hcb lo dcais new rqdiv€ dy6 .c@rdiis
ro ire modifietio, of Ihe
dcv.lop.d f.3tures. In rh. cud€nt stu(ly w rcponcd
&e appticarion of lhe CoMIA
mod€ling oD
rd
r.acrive dlrs. CoMIA has becn applied
ro denve rh. relatonship
Dct@n lhc atnenlat hodifietion
iillMe
of ihc
cee
Tlt.
o! l[c
wo*
dil're
deals wirlr
o.t
fotu of
ab5o6dvity which
rc<t
e.tiv. dr!,
dE
bindhe
the
dier indiqtion
d eltut@,
dimc6 of Ed E&ijve dys. fte ,.6on fo, $e
sle.tion of i!. dirnmo fonn is that rhe monoh$
has low aninjty wiih low soluble
pot dial yith ellulo$ fabric,
a llu.s a lcs ioL@tirc riDctionat g.oup. Howvs,
on Fphe|@lof rbe dim.!
fon 5, dlrric chdg6 wcrc ouwld in 0E !ffidty
of
rh. @ctivc dy6 wirh r[e eUu]o$ structu&, ,ft@foF,
k sleLd
sri*
hclp
th.
of the r@rive dycs for ih. 3DeSpR
u
to
nodify lhen sirucrurs. Iinally,
Dodificd $DctuEl f.ahfts hel,
c€Uulor.
b
ger
fb.i ll|c wolt ltow s@r.8y is
!Mi.!
i.!Ic rcsulrs
EoE
to
dim..
pr.dd tn hodcl whicl
cordd
dc,noEtlar€ rhlr the ouislaodirg
i
dacr,on of reactive dyes wirh the
repE*nrcd in wk S.b.Bel.
|I9
Chaptet
S.to6l
L
Resutu
&
Discussion
n od( now S.bcn fd CoMrA Mod€lu8
t20
Chapter 4- Result
& Discussioh
Aligrfrert Protocol vtth Dtfer.rt Chuses
ws sl6t d for th. dignmot sd t!. 61of dF Dolould
qelt aligned o thc $k t d @F structur., using lhc dala h6$ .ligricnr nethod of
Sybyl?.3. Th. aligcd conpouds v,@ depicl.d i! riglF2 ofch.Fs 3. To gct lhe
b6t CoMIA rno.tel, lhs. ditrcleni chsscs nethods w€rc apPu.d And duccBsful
The
omotr
3kcLton
.h4ge mctlpds (dab not shoM), w
consideFd anoihd ncthod fo! the sludy, tloM s MM[F94. Bv alplirg tlE
MMFF91 chqgcs ad slNfflitrs pNtocol on thc taini!8 ed tcst *ls, w obraincd
r€$lts by CsiLigd Hiickel
8@d
ed dntbc.
s{risical rcsdis. $ sho*n
31 at ls t ics oJ Co
in
Trble?of claF.F3
WA Ih de I
sl.c&d fot the lllining sd out of rhc bl'l
'IlD mainilg itu@
twdry.six (26) @mpoudr !o d.v€lop thc CoMFA nod'l'
th' CoMtA mo&L
conpounrb w€rc utili.d 6 &sl 3.t for rhc dtdnsl vali<tllion
Twly [M
(23) @bPoulds
*tE
'f
The PrS ncthod gives stisf@tolv.cads in ldm of
q'1
sld n
wls'
cxhibiting &e
nod.l nE outcod' of th' PLS edvsis is d'picled in
ad lt€
T|bltsl. Thc Frits indicded [|,t lo$ on o c6s ltlidabd q' = 0 529
robushcas of lhe ddcloPcd
n=
0.98s. The
el6to$atr( n.U cooEibudon i5 assMcd ro bc !o sEe s&dl
domindt a! conpaFd to the stedc ficl4 bui
sibilar lcEl of
I.blF
st
aglh in ficld
i! t€
bread
3Fat!4 bob ltelds bive
crdribulior'
AlalvsisL Sr.t'tdical R6ults for R.d R.aclivc DlEs Extr"tcd bv CoDL
591.21
l2l
Chaptq 4. Re8ult & Discussion
a: Closs'validai€d corclation
celficiat
(q2); b;
Oltinm nmb.r of @bpoMrs
Ftdictid (SEPI d: Sidddd .rrcr of 6im*
cdmion l @l.nor @fEci6t (.2); f: Cofrl.lion @fttci6r G2Fed).
(ONC);
q Sta'ddd .@
3D Anqtsts olthe
of
(sEE)i c:
coMrA
Orc of th. nosl intercsting.nd innor@tivc
qdlr.!
f.ltws
of
tl€ CoMFA nDdeling is ltE
@ffcicnt @nrou plor& Thc conioE mF we
wil[ c!.h CoMFA @lum. TIF
s@nLd G *51& Fodlcts of @frcidts
'ssiaLd
rcsios of havins $aled ctrciots sr€atlr thd 8ryo (favoEd) or l6s thn 20%
(dkfavoEd). ft€ tw fi.lds of CoMFA nodek for th€ alalyeis bosd on ihe d!lab.$
vi.uslizlio. of t!.
3D
@rou plot!. Th€ @lored polyhedbl in th. m!
smud.d .ll lanie Finls *t!.e lh. 3DQSPR is slroDgly sial€d *ith lh.
chrngG @uE€d in lhe conpouds field vd6 wilh Bpet to lterbijvity potential,
FiglFl (. dd b) depid th. d€tic .nd cl*lbstatic cdiou maPs of CoMFA
aliSr|Ml Rw F€st d
&s
(SrD.v.C@fl) nodel. Th. clrrou m.ps of clccndt lic 3nd nsic c@r,butroN shoe
@liE dt6. To aid i! th. vi.qtI"nrio4 dlDu
mp6 swuld th€ t nplst rdoldul€ 61 6 a Ef.@ conpoud dE b highcn
etul
potcntid ir lb. d..ign of mw
lb.o'brivily which indicaid high afrnity wi$ the coton fabdc. In . SLric ft€lds
fsvord for buliy gmup3 (rre!) and djlf!rcEd fd bulky greup (FUow) *hiL in b
Eleftn
tic 6ckls fawEd
fd esEtiE
greup
(d)
atd diibvotld rd
ft8.tiE gorP
Chaptet 4. Result
Fig.Fr (.
!d
&
Discussion
b)
th@ Ieg€ bl@ isoplcths @vq rhe Ed r€&iivc dvc due 10 lh€ niireg.n no''tv
vlich shos lh,l th* ,M N itrtcEring wll with tlE E8lrive ponion of lhe
The
celluloe. In lhe
n&6s!y for
.ll th. @lduls which h
dye stroctw, th.Ffo€, the r€d @n1ou show th€ b€nd
ptsnt w.lq
the
@
dE niiroSo is coNflGd for
vdialio! iD the datlsi S.vdal rcd 6rtod 9d fould rd tte Ngdive chaec
moieli€s pEdomimily b.caue. oI $e hvdmxvl tld 3ulforuc gbups Tho*
conpounds
wirh
6t
*bict
hav€ rh. srtlonic greup harc the
of 6€ srou!6,
.d s ! GuL
bigLd
6s, 61, 51, 5b
.td
in
@ipei$n
5c ahow g@d
skdbtivilv
atedivitv
vzlidation o! the 3D-ps'PR Mod.l
nr@ $16Ld @mpo6&
vw
nodel. The cahul.tcd esulk
e
us€d
s
lhe
lisned in
td *l
ro
vdifv
lhe
T.blF? of chipter l-
@nsel€d CoMIA
Th€
predictd
l2l
Chdpter 4. Result & Discursion
e
dpdindlal d6t4
.nd h a slltblical tol€Eble raagc, qith iL cdrelation co€ffi.idt ofa= 0.'l97.TlE
tcsl rcsulb indi.ated thd rhe CoMIA rDdcl i! Flirblc and h6 g6d pEdictiv.
absorbdvity for l!€ CoI{FA modcl
in Sood agrccm€nl eilh lle
ability.
R6Eli .nd Dila$ioo of Analiicmbi.l A.rlylty
In thc
prlgt
ard thinen
foud
io b€
shtdis,
peel
cdE !eg.tiv. b&t,ri!
9m.
cotnpouds
All
spld
iL
teicd agai.sr fiften C@ posiliv.
conc. loo|lg/El.
AI
the
@pl.s v@
qmi!€d ag.jnlt thin4n Om-negative nici@.gdisns
of 100 pglml. 5l md
Eru9 wir.l ZOI of
ZOI of
st
wc
i@tive aeaiNt all Cran pGitirc b&t da.
All fic @mpoolds w.&
rhc conc.
3rnth.ric dy6
9r!.
5h
tn
dd 5*
slDw.d lctivily agajnst ,rdi, ei.hta
shovcd eriviry agalnsl Snige a
5f also showd activttr
{Ee
inaclive
,'@
!g.i$r
sll
asiBt
ib
dtert*r
ATCC
dtwtery
vtll
with 1l ZOI
ne
oud cED rcgalis bactdia
bsrcd lgaiGt fourEd nDgi
FaariM tp, Peiici
Shise a
.oI
at
lecly,l4,4rt(
Nigq, A. JtM,
Rhtaps sp., Can li.ta atbicfu, C albi.M /rcC
0381 Sach@ontres codisi@, Miqosponn @it, M gse,.,,, Ttichophtton
tubw,
T.
sp.,
n .lagophtta.
T.rotB@B a
d
H.Ittu tthosprun tp, art$ coe.
IOO
Fdml, 5c w imctiy. aeain$ all frDgi bui orly lbo*cd modeate a.tivity !g.i!st
Mcdr& with zOI of t3m whilc all olhcr compow.ts lft imcrire asainst aI the
tungi al th€ @nc. of 100 pgls .
t24
Chapter 4. Retu
TrblF 2Invilro
A
ib&rdid A.livit(Zon oftnlibitid
Grn
P@nv. B.ct
in
&
Discussion
m)
ri.
CoDp.ud! m& /corporn.b @d.
Nd.otrllcre org.trbbt
*
2
3
C orw b@ r. I I
M.l lplu h. i d
5
corwbd.nM
6
Cortnebdctilun xercsls
8
$@ctu
holna,ni
l.uns ATCC$1r
9
l0
ll
gapbte@tu MB-4BIEE
12
slophlococtu efuemidts
l3
l4
Strcpt@tu tapophtrtcq
It
125
Chapter 4. Result
& Disc6sion
Trble'3 Invitro Anribdcrqi6l Acriviry (zonc of Inlibitio. in tnn)
Gnn Ncartlv.
hd.ri.
Coopou&
NrDe of olcrc orgrtrirb.
2
trd. /onpo!!d! @d.
f
fi
E ch$ichia colt ATCC 87 39
9
3
E@li ntht .!dg
r.skt@.
5
1
PsetdadoMt anogkNa
8
Pseudononat
etugln^o
rtTcc
9
l0
ll
t2
9
l0
l3
t26
Chapt.r 4. Result & Discussiok
Trbl. -{ Invilro AldnDeal a.livity
(Zooc ofiDhibilion in
m)
CoEpoubdt n.me /corpoulib coile
N.n€ ofElcro orcdbnt
,9
2
J
5
7
Cddlth albtca, ArcC 0J6l
Sa4huoDrees cet vitiae
9
t3
l0
ll
t2
Tr i. hop hr,t o
"
n
g ophtr e s
n ta
l3
l4
t27
Fastness Cards of Reactive Dyes
(5a- 5m)
128
Clap@
4
netult & Dbcrttion
h. md.: ,.
Fptrd P@ni.:
T1D
follNins ftirEs !6pcni6 wE
11. d.4h ofsh!.L is I%
TESTNA
i!
rt
resred on
follosins
dy.ins of
indivitd
.|@iz.c
@non rovcn bv
@
E
3
D.tliglift0Fd
MB|Ildp
:
lso lotAo2
at 20Hos&40HoE
,L
s..H'a,-
tsGcol
s.p 5 !/r. edim c.lno@ etydtu
60'C, J0 nin. liqbr dio | : 50
2
sn,
-_r-+.:t'\
't29
Choptet
4
Resuh
&
Discussion
In..od.: t (d)
II
l,
i30
Clspter 1. Retuh &
Drtlrritn
I)v...dc
Diswnn
2009
,f,
Irrr.tsr&
Tlt folloling
es6! p6t
rri..
re
@d
Tn {LFb ofs!.d. i! l|6 i! rh.6]}fli.a
@
dttila
idvii.l
of
ffiiEd
o|lon
M
bv
Ls.
IEIII !&
D.tligh odtod: $o l0r*02
MBTFldp d 20l|oor +aoEdc
lso{o3
sp
5
s4
6OoC. 10
I
$diE
6to!- l$w
$
mil liqu rnio l:
2
t/L
l.ll
Chapter 4. Resuh & Discustion
rij'idhmdry&6}IoeiehydrE0'5s/
s.dib db'r4a
dr.oqd. ddryd* t.r
?
€
=
r4li@d60tfu]oDid
vd$cjminoaniEr,idnh.
p6 n ir pL6 Ni![ F of r2l rP.
*
'::
I
ll2
Chapter 1. Resul &
Ditclttion
I}nd lsd,.,m
'nr rollNiis frnEs
Fopcnid
w
er.d
on
,l\titrg dt
nsdiz.d @nd
sor
oh
rh.&dlotdd. 3 r".nd.r. @r,{u|(jl,duaj@
TIST N^M[
Dry|igh4dhod:60l0J-80,
ros I sA bdr4 c.Jro@ Dbrd@
6{rr D n,n hqer dd | 50
2
rl_
l3l
Chaptet 4. R6uh & Discussion
t
\r.& d.,c Jz-sbm!
I|lddaErhyddd&IhiDeul.I
s!/l
Hi@di}y&tFdi.pd..'6.|.ddydu,l,]
L'tl'idnimrci'{d|6&mdYd*o'5d
5d'
DisodinoniodEd.r
s;Jl
(q5bl dt
3
0.
tqc.
4
in)
|]f|s'Fin6i!ilbl.dAli.dE
prd
n
ii pnB riri F
-
or 12
j
rA
I
I
134
Chap@ 4. Retlit & Disctssion
Brrdir---L
ESorl4rrdgi
TL follotil*
r..|tBpr.Fti6 MtBdtddy.insor@iz.d M
It d.t}ofid.n
l9a
hrh.
follo*i4i
i!6
t^
i.i'lurl'.r-
Dlyridr mrr.d : Iso 105.802
MB1Thop d 201106
s..p
5
4
6O.C. 30
lodiu
+ {0
l{oN
qboe."t''dru r /,
m. liqE di.
t: 50
I
i
135
Chaptet 4. Resuh
&
Discussion
*,.d-FE*.''._
:l
L+ic;dhlrni'dEnbd&dNDh'da.oJcl
r.,
i
sodud,iFryd bF\oebr &byd& I!!1
rb'idi.'idEn,ddnkidcm@tjdrk0J!i
&dimGtnclqL.
(q{! Pn 3.0, r7r. 4 hh)
ltEtdjFiHisinn.Bdin!*
:bEtiqu d 60rc tu r0 hii.
wdFimliiD.rirdjz.d@'
id ,rb lirt F of t2., kPr
Dhln r
r0i
5a
I
I
t
i
136
Chapt r 4. Retult & Discusion
-tr!:lti!!!l!o9
&Elo4il
1rr lolloving f.st:B
Thc
roFti6 EE
E
td d
dy.itrs
orMdir.d M sd
b\
&rI6fd.d. i. l% h rli hllou{ urliv 4r4
Drylishl.Elhod:nol05.Bo!
MBT!loD d 20Hq6iaoHo$
sr'&.h.r!.:-!1 shl|i4+-
5 c/. $diM dtom rdrnru
6fC, l0 ritr, lha 6!0 I: 50
$p
2
!4,
tt7
Chapter 4. Result
I"a-a.d.rti!.ddbd'lr.r.
3o&! dj|!Id.F
drbtl..dc dd'dd
LJI'|...dre.&il
todtd-
&
Discussion
t
tb-di-.rc
r.ti rir .6{.c nn '.r
t r-il-g-,
d..ra riF.!s td't ri
5
",1-
,.-11
138
ChaDter 4.
Colpr
Renl. & Discutsion
l.ttft:! T6tipe
139
Chapter
Colpr
L
Resalt
& Dkcuttlon
Fur...| T..dnt
T..t & Reull':
t40
Chaptet 4. Resuh
Color
& Dic.utsion
F.ttr6. T..ri!q
t4t
Chapter 4. Resuh & Discwsion
Color
tr'|th.s Tcldnp
TG.t & R€6ult$
t42
Ct@ter 1.
R.ttl
&
Itbcartloo
cs!9r-ttrllr-IEger
RBSULTS:
t l-rr|oa4qt
l,l3
Chopter 4. Resuh
Color ['rrtr.[r!
& Disc6sion
Tdtirs
T.rt & B..riltr
t44
Ctader 1. Retal & Ditclttion
Colpr
T.rn.rr
T..th
EESIII.B
ta5
Chapter 4. Resub & Discssion
Color tra!tn..! Te8tirt
Tc.. & R..uh!:
t46
Chtptet 4. Result & Discussion
Color
I!.lre|!
T€rtins
t17
Chapter 4. Resuh & Discustion
Ce!er-&4!!s.IES!g
Tc.r & R..ult !
t4E
Chartet 4. Ret'Ill & Dbcuttbn
Ca&r.&d*-I!d!8
la9
Chopter 4. R6uh
&
Discussion
Color Fr!tu..r T..titrs
T.6t & Rc.!rh.l
150
Chaptq 4. Result & Discusston
Cobr F.dr...
T..tirr
t5l
Chapter 4. Res lt
Color
& Discitsslon
f.rtnd T.dtr!
TdtLr&
152
ChaDter 1. Retult
Color
& Disclttsion
Fr!.rd! Te|.int
t5l
Chaptet 4. Result & Discuttion
Cobr tr,,3tn.$ Tdtirq
Tc.t & n
ruln
154
Chapter 5
Conclusion
Chapt€r 5: Conclusion
A&n s otr,r-@ twtive drs @ aining1{4,tuicNoctl,3,5luieid-2-yleie),
5'hydrcxy-dphthal.n "2,?.dirulfonic eid as @upling moi.ty hav. bcd synth.siad
by @nvdtional D.thod md thln f&e!* prolErti6 $nrinizd by a?plicllion or
lsill otton
f.bric. Thc d.dvarivcs of prcMt invation povide norc
inr6e dyeing
Nith h!6 red 10 purplish blue, deFndi4 o! th. dift enr di@ @nFnc ! ir
@mbimtion with difttur bridging Sllups ui.d- n cxh.$lion ed fixarion valH
br aI th. dy$ e vcry good which is d$ du. to incrced nol€culd widrt which
.ol&c€d dimrsiotr to girc uifod sbade qithour .ddinon of dy lcveling a8dr on
*ovo fibric in exlaul dy.ing shicl h tum shov riSnifcrnt inptuvcncnis ir
Ed@ing sp.nl dyaiuffin €muent, incr@ilg dy€ !ffiniry
oflt
th. .fficidcy
dy.aubcuirc
o$lor @rioa sd
10
the subsrlte,
siDluryilg
iDcBing
the posr
dyeile
'Soapine off prcces" rBdirioMlly sociaLrd with fib€l re.ctiv. dycs snd sho\r fan
Toluidine
6
a
gmup
h
b
dieo@mpo!@i favoB moF fixarios in rhcse Lindr of dy€e
simildly DASDA bridging is al$ h.tt{ 0!an other bridSins ir c.se of $dsd dtts.
Th* dlB e
.einogdic
ale Bld a
a sub6dnne for
bcEidin dts whjch lbow dang.ou
propeni€s. Dys contrinine H.aoid
rilh
monoftlcrional coDlonenl[ad
no1 high
.xhaustion th@forc thcy
ar
synthesis
w
exhlutio! wlich shos lna! lhe6e dy.! dc
fohd .xcell6t
ro good
b.n r for p.d-barch dy.ing bln io presed
ds
moF b€ttq for pad baich dtlirg. Wsshins f61n€s 3how ex*ll.nt slBdc .hege
*ilh nod.r.l€ lo
thm @t!on, which is favonbie
h$ to b. improved in futur
@@.rcirl dya
*fiI.
f.btis ar. b.[d
in @mercid laudding. Hov€vcr, th. lidt fesbss
good stairirg
o! @no!
m*
stairirg on othq
t3 it is fair to p@r, $licb is @mprnSle wiilt nost
for .pplicd d.rth of3hade.
\'@ t$t€d lgaist tili.en Gr@ positiv€, thiied Gm
!.gatiE b6ct .ia ud found tungi .t thc @c. 100F9/rbl. only 5c $os nod@t
activity agai$t on tungi &.orir wilh ZOI of l3M phich ha nrlphomte grcu! at
Prsenl syn$elic dy6
D.ra p$idon of diazotizd
eirc
in
@u
in8 lg€nl whil. its
isa
slDs no aclivity. Siructrs wjrh DASDA E a brid8ing moi.ty
position in dnEtic dietired couplile is i@tive in .ll t€sh.
pd portion
c!6 with m.ta
!t
l5t
Chaplcr S Concl6ion
whire 5r &d
5b showd
9m. S[ ed
acnviry r$nn$ Eehetkhta coli
lrcC
8739
5k shoNld actritr 6sn^* ShiSeIo dt$ent.ry wilh
Although 5l also slrowed acrivity agn.f/ Shii.fia dyse"tery
*itt
11
vb
Zot ot
zol of 9m
ZOI
In sEilctws of 5k, 5l dd 5m. r-Toluidine as 6 di@tzed mMlic dine in
@upli.8 agcnl is pFsni whil! in 5h p"loluidin€ b prcsi' whrch shows 'Cllr at
positior is ravorable ihen paa which in ffi bcte Zol at m.t! position ln
',,a
hs rc scrivity also hs
aligmcnt a l,4phcDyl€n€mine.
5h who
In the pr€s€n1sludy,l!. tb@
(3FQSPR) &chniqu€s
M
dinedidal qwtlaiiv. slructu. prop'nv rcLtiochip
ued io alPchend thc lcd cadiv€ dvd int€dclioN
lhe ceUulosc by thc Codlarati!.
m€tlbd
pan
Proluidinc bui iG bidging eouP ako har
ws €fie.lilely ulilizld
Mol*uld
Field Analvsis
tith
(CoWA) melhod 'ftis
to fol.casit a Eliablc modcl
'fte foE aded do<lel
n sN morc qdhcd
siv.s sar'sladoty sbunical rcsults !!d in d. lighr of lh*
Mo@!cr, the gnphicd tsulls (co!to!r m!9s) aid b undcd'nd the @cndm'!t
'fte
pa|r.m sd onPN th. sl$ch!.t vsiatio6 with rs!@l ro th' sbsrptivity
$dic fi.td hd d8M ou
dvd:
ifw
dEnnwo
@uld
ilclte
d sire BoE
sttenliotr to*a.ds
thc sllal c!ai!
si8'lific!
ib. bulkincs of prts{v
of$c
bddsrne moietv io rhe
inlendion. Thoe
'vnrhcsiad
lirns
Dol{ul6 *ttich!'E
wrt
sulfoDc
hd. hig! ab$rptivitv r.ruca b.caue $k moietv ltlpc to sohbili4 the dvr
Foldlc isidc thc fabic but 3ho* 163 fxaton in fdtn'ss tcars Thc intomalion
thc afiinitv of
obtain d ton the 3D-QSPR nodcl Dav Povide a rool for PE{ticting
goups
w),roM sldcNes priot
well
d
nor-toxic for
10
its svnhcais {hich could be bcst for the
mvimMht lr
cclhlos fibs
addition, the ultimate sd'cted Dodcl
$
hs
tesl sel This studv wort
suftcicnl potenlial to undedlan.l the poperq of the
'xtloal
atrDtv ed sel'ctivitv
could be bcn ficial to jultify the !.w r$.tiv. dv.s with bclcl
156
Crnprr 5: Concl'r',ton
ktl.rdotr
l.
Aii,& Prw.a'z Qfri N.AdLta'
U. lrM,8.Xd,3.r
K. lit Kl!!. S. Pt v!.o !!d lt Vo.le( ' 3D'QSIR. Mdhoil ol
cddkol Tcdin Adi.d d Rd f.riE D'.. bt UirS CoI{PA
bl l2'p.t!6?'
id',! h;,'d
wfu tu
EE7t,
f,lc l0ll,
6Ye
wt
I5?