Polymerisation Processes Polymerisation Processes Polyethylene ...

The Nylon revolution 1945
O O
N (CH2 ) N 6 C (CH2 ) C 6 n
H H
Dr. Klaus-Dieter Hungenberg, BASF AG Ludwigshafen Vorlesung Polymerisationstechnik, Universität Paderborn, WS 07/08 Polymer processes
Polyamides – base materials
ε-Caprolactam: OH
+6H
(Ni)
OH
H
-2H
O
+H2NOH -H2O N H
Phenol Cyclohexanol Cyclohexanon Cyclohexanon-oxim
Hexamethylene diamine:
Adipic acid:
+6H
(Ni)
Benzene Cyclohexan
H 2C = CH – CH = CH 2
H2C – CH = CH – CH2 CN CN
+CINO
- HCI
(H 2 SO 4 )
H2 C
H2C CO
H2C NH
H2C CH2 ε-Caprolactam:
Dr. Klaus-Dieter Hungenberg, BASF AG Ludwigshafen Vorlesung Polymerisationstechnik, Universität Paderborn, WS 07/08 Polymer processes
+Cl 2
+2H
(Ni)
+2NaCN
H2C = CH – CH = CH2 -2NaCl
Cl Cl
NC – (CH2) 4 –CN
+8H
(Ni, NH3 )
H2N – (CH2) 6 –NH2 Adiponitrile Hexamethylendiamin
H2C H2C CH2 C
H2C CH2 H
OH
H2C H2C CH2 C = O
COOH
(CH2 ) 4
H2C CH2 COOH
Cyclohexanol Cyclohexanone Adipic acid
73
75
Polyamides – basic structures
PA 6: Perlon PA6.6: Nylon
O
NH ( CH ) 2 C
NH ( NH
5
CH ) 2 C (
6 CH ) 2 C
4
n
n
PA 6: Caprolactam
PA 11: Undecanlactam
PA 12: Laurinlactam
PA 6.6: Hexamethylendiamine
+ Adipic acid
PA 6.10: Hexamethylendiamien
+ Sebacic acid
PA 4.6: Butandiamine
+ Adipic acid
Dr. Klaus-Dieter Hungenberg, BASF AG Ludwigshafen Vorlesung Polymerisationstechnik, Universität Paderborn, WS 07/08 Polymer processes
PA6 – basic reactions
1. Ring opening
NH (CH2 ) CO + H 5 2O H NH (CH2 ) COOH
5
2. Polyaddition
NH (CH2 ) CO + H NH (CH CO OH
5
2 ) 5
3. Polycondensation
n
Dr. Klaus-Dieter Hungenberg, BASF AG Ludwigshafen Vorlesung Polymerisationstechnik, Universität Paderborn, WS 07/08 Polymer processes
O
H NH (CH2 ) CO OH
5
H NH (CH2 ) CO OH + H NH (CH CO OH H NH CO OH + H2O 5 2 ) (CH 5 2 ) 5
n
m
n+1
n+m
O
74
76