Pol
y
mer
i
zat
i
on:
Sy
nt
hesi
sofNy
l
on6,
10
C11522
TeacherBackgr
oundI
nf
or
mat
i
on:
Pol
y
mer
sar
emacr
omol
ecul
esbui
l
tup byt
hel
i
nki
ng t
oget
herofl
ar
genumber
sofmuch smal
l
er
mol
ecul
es.Thesmal
lmol
ecul
est
hatcombi
newi
t
heachot
hert
of
or
m pol
y
mermol
ecul
esar
ecal
l
ed
monomer
s,andt
her
eact
i
onsbywhi
cht
heycombi
near
ecal
l
edpol
y
mer
i
zat
i
onr
eact
i
ons.Ther
emaybe
hundr
eds,t
housands,t
ensoft
housands,ormor
emonomermol
ecul
esl
i
nkedt
oget
heri
napol
y
mer
mol
ecul
e.Mol
ecul
arwei
ght
sofpol
y
mer
smayr
eachi
nt
ot
hemi
l
l
i
ons.
Ther
ear
et
wot
y
pesofpol
y
mer
s:Condensat
i
onpol
y
mer
sandaddi
t
i
onpol
y
mer
s.Thef
ol
l
owi
ngt
ut
or
i
al
descr
i
besbot
hpr
ocessesi
ndet
ai
l
:
Tut
or
i
al
onPol
y
mer
i
zat
i
on:
ht
t
p:
/
/
www.
auset
ut
e.
com.
au/
pol
y
mer
s.
ht
ml
Ny
l
on6,
10,
whi
chi
st
hepr
oductofacondensat
i
onpol
y
mer
i
zat
i
on,
wi
l
l
bepr
epar
edi
nt
hi
si
nv
est
i
gat
i
on.
Oneoft
hemosti
mpor
t
antki
ndsofny
l
oni
sny
l
on6,
6.I
twasi
nv
ent
edi
nt
hel
at
e1930si
nt
heUni
t
ed
St
at
esbyWal
l
aceCar
ot
her
swhowaswor
ki
ngf
orDuPont
.Ny
l
oncanbesy
nt
hesi
zedbyacondensat
i
on
r
eact
i
on.Acondensat
i
onr
eact
i
oni
spol
y
mer
i
zat
i
oni
nwhi
chmonomer
scombi
neandasmal
l
mol
ecul
e
by
pr
oducti
spr
oduced.Theby
pr
oducti
susual
l
ysomet
hi
ngl
i
kewat
erorHCl
.
Thesi
mpl
estcondensat
i
onr
eact
i
onf
ormaki
ngny
l
onsi
st
her
eact
i
onofadi
ami
neandadi
aci
d.The
pr
oductoft
her
eact
i
oni
sapol
y
ami
de,
orny
l
on:
H
O
O
║
║
H2NCH2CH2CH2CH2CH2CH2NH + HOCCH2CH2CH2CH2COH
HO
O
│║
║
H2NCH2CH2CH2CH2CH2CH2NCCH2CH2CH2CH2COH +H2O (
Ny
l
on6,
6)
Al
sor
epr
esent
edas:
H
HO
OH
HO
OH
HO
O
│
│║
║│
│║
║│
│║
║
nN(
CH2)
NC(
CH2)
CN(
CH2)
NC(
CH2)
CN(
CH2)
NC(
CH2)
C-+5nH2O
646464Maki
ngny
l
oni
sev
eneasi
eri
fy
ouuseadi
ami
neandadi
aci
dchl
or
i
dei
nst
eadofadi
aci
d.Thi
si
sbecause
aci
dchl
or
i
desar
emuchmor
er
eact
i
v
et
hanaci
ds.Ther
eact
i
oni
sdonei
nat
wophasesy
st
em.The
ami
nei
sdi
ssol
v
edi
nwat
er
,
andt
hedi
aci
dchl
or
i
dei
nanor
gani
csol
v
ent
.Thet
wosol
ut
i
onsar
epl
acedi
n
t
hesamebeaker
.Ofcour
se,
t
het
wosol
ut
i
onsar
ei
mmi
sci
bl
e,
sot
her
ewi
l
l
bet
wophasesi
nt
hebeaker
.
Att
hei
nt
er
f
aceoft
het
wophases,
t
hedi
aci
dchl
or
i
deanddi
ami
necanmeeteachot
her
,
andwi
l
l
pol
y
mer
i
zet
her
e.Thi
si
st
hepol
y
mert
hatwi
l
l
bepr
epar
edi
nt
hi
sl
abandi
scal
l
edny
l
on6,
10.
I
ti
spossi
bl
et
opr
epar
eapol
y
merf
r
om onl
yonet
y
peofmonomert
hathasanaci
dgr
oupononesi
deand
anami
nogr
ouponanot
hersi
de.Ami
noaci
di
sanexampl
eofsuchamonomer
.Thecondensat
i
onof
ami
noaci
dspr
oducespol
y
ami
noaci
dsor
,
i
fnat
ur
al
ami
noaci
dsar
eused,
pr
ot
ei
ns.
Thenameoft
hepol
y
meri
ncl
udest
hewor
d"
ny
l
on"f
ol
l
owedbyei
t
heronenumberort
wonumber
s.I
ft
he
ny
l
oni
smadef
r
om onet
y
peofmonomer(
l
i
keami
noaci
d)t
her
ewi
l
l
onl
ybeonenumber
.Buti
ft
her
ear
e
t
wonumber
s,
t
heny
ouknowt
hatt
heny
l
onwasmadef
r
om t
wot
y
pesofmonomersy
st
ems.Forny
l
ons
madef
r
om onet
y
peofmonomer
,
t
henumbert
el
l
sy
ouhowmanycar
bonat
omsar
ei
nt
hemonomer
.
Hence,
i
fny
l
oni
snamed"
ny
l
on6"
,
y
ouknowt
hati
ti
smadef
r
om amonomert
hathassi
xcar
bonat
oms.
Forny
l
onsmadef
r
om t
wot
y
pesofmonomersy
st
ems,
t
het
wonumber
st
el
l
y
ouhowmanycar
bonat
oms
ar
ei
nt
hedi
ami
nemonomer
,
andhowmanycar
bonsar
ei
nt
hedi
aci
dordi
aci
dchl
or
i
demonomer
.For
exampl
e,
i
fy
ourny
l
oni
scal
l
ed"
ny
l
on6,
6"y
ouknowt
hatt
hedi
ami
nef
r
om whi
chi
twasmadehassi
x
car
bons,
andt
hatt
hedi
aci
dordi
aci
dchl
or
i
def
r
om whi
chi
twasmadehassi
xcar
bonat
oms.
Phy
si
cal
Pr
oper
t
i
esofNy
l
on:
Whydoesny
l
onactasi
tdoes?Whydoesny
l
onmakesuchgoodf
i
br
es?Theanswert
obot
hquest
i
onsi
s:
i
nt
er
mol
ecul
arf
or
ces.I
nny
l
ons,
t
hemosti
mpor
t
anti
nt
er
mol
ecul
arf
or
cei
shy
dr
ogenbondi
ng.The
ni
t
r
ogenbondedhy
dr
ogenat
omsofoneny
l
onchai
nwi
l
l
hy
dr
ogenbondv
er
yst
r
ongl
ywi
t
ht
hecar
bony
l
oxy
genat
omsofanot
herny
l
onchai
n.Thesehy
dr
ogenbondsmakecr
y
st
al
sofny
l
onv
er
yst
r
ongbecause
t
heyhol
dt
heny
l
onchai
nst
oget
herv
er
yt
i
ght
l
y
.Ofcour
se,
t
hesest
r
ongcr
y
st
al
smakest
r
ongf
i
br
es.
Pol
y
mer
i
zat
i
on:
Sy
nt
hesi
sofNy
l
on6,
10
St
udentAct
i
v
i
t
y
/
Demonst
r
at
i
on
I
nt
r
oduct
i
on:
Whati
sanexampl
eofsomet
hi
ngmadeofny
l
on?(
Hav
esampl
esofcl
ot
hi
ng,
t
entmat
er
i
al
,
hosi
er
y
,
a
t
oot
hbr
ushet
c.onhandt
ohol
dupasst
udent
sanswer
)
.
Ny
l
onsar
esomeoft
hemosti
mpor
t
antf
i
br
espr
oducedcommer
ci
al
l
y
.Al
otoft
heny
l
onpr
oducedends
upascl
ot
hi
ng.Butny
l
oncanbemor
et
hanj
ustf
i
br
es.I
tal
soendsupasot
herev
er
y
dayt
hi
ngsl
i
ker
ope,
t
ent
s,
andt
oot
hbr
ushbr
i
st
l
es.Somet
i
mesny
l
oni
susedt
omaket
hebel
t
st
hatr
ei
nf
or
cet
i
r
es.Most
passengercart
i
r
eshav
est
eel
bel
t
s,
butr
ei
nf
or
cementf
ort
i
r
esf
orai
r
cr
af
t
,
t
r
ucksandof
f
r
oadv
ehi
cl
es
ar
eof
t
enmadeofny
l
on.Ny
l
oncl
aycomposi
t
esar
eusedt
omakeunder
hoodaut
omobi
l
epar
t
s.Ny
l
oni
s
usedf
orsel
f
l
ubr
i
cat
i
nggear
sandbear
i
ngs.Ny
l
on6,
10,
at
y
peofcondensat
i
onpol
y
mer
,
wi
l
l
bepr
epar
ed
i
nt
hi
si
nv
est
i
gat
i
on.
Mat
er
i
al
s:
Ny
l
on6,
10ki
t
scanbepur
chasedonl
i
ne:
(
oratv
ar
i
ouschemi
cal
suppl
ycompani
es)
ht
t
p:
/
/
www.
onl
i
nesci
encemal
l
.
com/
Shop/
Cont
r
ol
/
Pr
oduct
/
f
p/
v
pi
d/
2584426/
v
pcsi
d/
0/
SFV/
308
52
Not
e:Themonomer
sf
ort
hi
sr
eact
i
onar
equi
t
eexpensi
v
e;
y
oumaywantt
oper
f
or
mt
hi
sasa
demonst
r
at
i
onandhav
est
udent
sanal
y
zet
hepr
oduct
.(
Thecostusi
ngpr
oduct
sf
r
om Fi
sherwoul
dbe
appr
oxi
mat
el
y$8perr
eact
i
on)
Hex
ane1,
6di
ami
ne(
1g)(
H2NCH2CH2CH2CH2CH2CH2NH2)
O
O
‖
‖
Decanedi
oy
l
di
chl
or
i
de(
1g) (
Cl
CCH2CH2CH2CH2CH2CH2CH2CH2CCl
Wat
er(
25mL)
Hexane(
25mL)
100mLbeaker
Gl
assst
i
r
r
i
ngr
od
Bal
ance
Pr
ocedur
e:
Caut
i
on:Pr
epar
ei
naf
umehoodandusegl
ov
esast
hemonomer
sar
et
oxi
candcor
r
osi
v
e!
1.Di
ssol
v
eabout1gofhexamet
hy
l
enedi
ami
nei
n25mLofwat
eri
na100mLbeaker
.
2.Makesol
ut
i
onofabout1gofsebacoy
l
chl
or
i
dei
n25mLhexane.
3.Gent
l
ypourt
hesebacoy
l
chl
or
i
dei
nhexanesol
ut
i
onont
opoft
hehexamet
hy
l
enedi
ami
nei
nwat
er
sol
ut
i
oni
nt
hebeaker
,
usi
ngagl
assr
odt
opourdown.Af
i
l
m wi
l
l
f
or
m att
hei
nt
er
f
ace.(
Seebel
ow)
:
4.Dr
awat
hr
eadoutoft
hi
si
nt
er
f
aceusi
ngaf
or
ceps,
anddr
awt
het
hr
eadoutoft
hebeaker
.Usi
nga
gl
assr
odasaspool
,
sl
owl
ywi
ndupt
het
hr
eadasy
oudr
awi
tout
.(
Seebel
ow)
:
I
tshoul
dbenot
edt
hatt
hi
spol
y
ami
dewi
l
l
cont
i
nuet
of
or
m att
hel
i
qui
di
nt
er
f
ace.Oncet
heny
l
ont
hat
hasal
r
eadyf
or
medi
sr
emov
ed,
t
hel
ay
er
swi
l
l
meetagai
nandmor
eny
l
onwi
l
l
f
or
m.I
nf
act
,
i
fonewer
et
o
pul
l
sl
owl
yenough,
qui
t
eabi
tofny
l
oncoul
dbef
or
med.
5.Af
t
eral
l
t
hepol
y
merhasbeencol
l
ect
ed,
washi
tt
hor
oughl
ywi
t
hwat
erandl
eti
tdr
y(
i
nt
hef
umehood)
.
6.Unwi
ndt
hedr
yt
hr
eadandl
ett
hest
udent
sexami
nei
t
sphy
si
cal
pr
oper
t
i
es.
Theequat
i
onf
ort
hi
sr
eact
i
oni
s:
H
O
O
║
║
H2NCH2CH2CH2CH2CH2CH2NH + Cl
CCH2CH2CH2CH2CH2CH2CH2CH2CCl
HO
O
│║
║
H2NCH2CH2CH2CH2CH2CH2NCCH2CH2CH2CH2CH2CH2CH2CH2CCl+HCl
(
Ny
l
on6,
10)
Al
sor
epr
esent
edas:
H
HO
OH
HO
OH
HO
O
│
│║
║│
│║
║│
│║
║
nN(
CH2)
NC(
CH2)
CN(
CH2)
NC(
CH2)
CN(
CH2)
NC(
CH2)
C-+5nHCl
686868-
Anal
y
si
sQuest
i
ons:
1. Gi
v
et
hr
eeexampl
esoft
heusesofNy
l
oni
nev
er
y
dayl
i
f
e.
2. Whati
st
hesmal
l
by
pr
oductoft
hecondensat
i
onr
eact
i
ont
opr
oduceNy
l
on6,
10?
3. Usi
ngt
heequat
i
onf
ort
hepr
oduct
i
onofNy
l
on6,
10abov
e,
i
dent
i
f
yt
henewl
i
nkaget
hathas
f
or
medasar
esul
toft
hepol
y
mer
i
zat
i
on.Whati
st
henameoft
hi
sl
i
nkagei
nor
gani
cchemi
st
r
y
?
4. I
dent
i
f
yt
her
epeat
i
nguni
ti
nt
hef
i
nal
r
epr
esent
at
i
onofNy
l
on6,
10shownabov
e.
5.
Expl
ai
nwhati
s
happeni
ngmol
ecul
ar
l
yat
t
hei
nt
er
f
acei
nt
he
f
ol
l
owi
ngdi
agr
am:
6. Thest
r
engt
hofny
l
oni
sdue,
i
nl
ar
gepar
t
,
t
oi
nt
er
mol
ecul
arhy
dr
ogenbonds.Expl
ai
nwhatwoul
d
happent
ot
hesehy
dr
ogenbondsi
fy
oust
r
et
cht
heny
l
onst
r
and.Whatabouti
fy
oubr
eaki
t
compl
et
el
y
?Cant
hehy
dr
ogenbondsr
ef
or
m?
7. Thepr
oduct
i
onofKev
l
ar
™i
ssi
mi
l
art
ot
hepr
oduct
i
onofNy
l
on6,
10.Resear
cht
hechemi
cal
r
eact
i
ont
hatpr
oducesKev
l
ar
™anddi
scussi
t
schemi
cal
andt
her
mal
pr
oper
t
i
esandi
t
suses.
Summar
y
:
Ny
l
on'
sout
st
andi
ngchar
act
er
i
st
i
ci
nt
het
ext
i
l
ei
ndust
r
yi
si
t
sv
er
sat
i
l
i
t
y
.I
tcanbemadest
r
ongenought
o
st
andupundert
hepuni
shmentt
i
r
ecor
dsmustendur
e,f
i
neenoughf
orsheer
,hi
ghf
ashi
onhosi
er
y
,and
l
i
ghtenoughf
orpar
achut
ecl
ot
handbackpacker
'
st
ent
s.Ny
l
oni
susedbot
hal
oneandi
nbl
endswi
t
h
ot
herf
i
ber
s,wher
ei
t
schi
efcont
r
i
but
i
onsar
est
r
engt
handabr
asi
onr
esi
st
ance.Ny
l
onwasheseasi
l
y
,
dr
i
esqui
ckl
y
,
needsl
i
t
t
l
epr
essi
ng,
andhol
dsi
t
sshapewel
l
si
ncei
tnei
t
hershr
i
nksnorst
r
et
ches.
Ny
l
oni
spr
oducedbymel
tspi
nni
ngandi
sav
ai
l
abl
ei
nmanydi
f
f
er
entf
or
ms.Thef
i
berhasout
st
andi
ng
dur
abi
l
i
t
yandexcel
l
entphy
si
cal
pr
oper
t
i
es.Ny
l
onsar
esemi
cr
y
st
al
l
i
nepol
y
mer
s.Theami
degr
oup(
CO
NH)
-pr
ov
i
deshy
dr
ogenbondi
ngbet
weenpol
y
ami
dechai
ns,
gi
v
i
ngny
l
onhi
ghst
r
engt
hatel
ev
at
ed
t
emper
at
ur
es,
t
oughnessatl
owt
emper
at
ur
es,
combi
nedwi
t
hi
t
sot
herpr
oper
t
i
es,
suchasst
i
f
f
ness,
wear
andabr
asi
onr
esi
st
ance,
l
owf
r
i
ct
i
oncoef
f
i
ci
entandgoodchemi
cal
r
esi
st
ance.Thesepr
oper
t
i
eshav
e
madeny
l
onst
hest
r
ongestofal
l
sy
nt
het
i
cf
i
ber
si
ncommonuse.Becauseny
l
onsof
f
ergoodmechani
cal
andt
her
mal
pr
oper
t
i
es,
t
heyar
eal
soav
er
yi
mpor
t
antengi
neer
i
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