GB1132952A – Process for the manufacture of copolymers of -ß-lactams
– Google Patents
GB1132952A – Process for the manufacture of copolymers of -ß-lactams
– Google Patents
Process for the manufacture of copolymers of -ß-lactams
Info
Publication number
GB1132952A
GB1132952A
GB868/66A
GB86866A
GB1132952A
GB 1132952 A
GB1132952 A
GB 1132952A
GB 868/66 A
GB868/66 A
GB 868/66A
GB 86866 A
GB86866 A
GB 86866A
GB 1132952 A
GB1132952 A
GB 1132952A
Authority
GB
United Kingdom
Prior art keywords
lactams
azetidinone
carbon atoms
specified
pyrrolidone
Prior art date
1965-01-07
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB868/66A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoechst AG
Original Assignee
Hoechst AG
Farbwerke Hoechst AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
1965-01-07
Filing date
1966-01-07
Publication date
1968-11-06
1966-01-07
Application filed by Hoechst AG, Farbwerke Hoechst AG
filed
Critical
Hoechst AG
1968-11-06
Publication of GB1132952A
publication
Critical
patent/GB1132952A/en
Status
Expired
legal-status
Critical
Current
Links
Espacenet
Global Dossier
Discuss
229920001577
copolymer
Polymers
0.000
title
abstract
3
238000004519
manufacturing process
Methods
0.000
title
1
238000000034
method
Methods
0.000
title
1
239000003054
catalyst
Substances
0.000
abstract
6
229920001400
block copolymer
Polymers
0.000
abstract
4
150000003951
lactams
Chemical class
0.000
abstract
4
239000002904
solvent
Substances
0.000
abstract
4
ZMXDDKWLCZADIW-UHFFFAOYSA-N
N,N-Dimethylformamide
Chemical compound
CN(C)C=O
ZMXDDKWLCZADIW-UHFFFAOYSA-N
0.000
abstract
3
-1
aromatic radical
Chemical class
0.000
abstract
3
239000000839
emulsion
Substances
0.000
abstract
3
239000000178
monomer
Substances
0.000
abstract
3
XMSFNEZQRPOHAR-UHFFFAOYSA-N
4-methylazetidin-2-one
Chemical compound
CC1CC(=O)N1
XMSFNEZQRPOHAR-UHFFFAOYSA-N
0.000
abstract
2
239000004215
Carbon black (E152)
Substances
0.000
abstract
2
RTZKZFJDLAIYFH-UHFFFAOYSA-N
Diethyl ether
Chemical compound
CCOCC
RTZKZFJDLAIYFH-UHFFFAOYSA-N
0.000
abstract
2
125000001931
aliphatic group
Chemical group
0.000
abstract
2
239000006185
dispersion
Substances
0.000
abstract
2
239000003995
emulsifying agent
Substances
0.000
abstract
2
229930195733
hydrocarbon
Natural products
0.000
abstract
2
150000002430
hydrocarbons
Chemical class
0.000
abstract
2
239000003999
initiator
Substances
0.000
abstract
2
239000000203
mixture
Substances
0.000
abstract
2
125000001997
phenyl group
Chemical group
[H]C1=C([H])C([H])=C(*)C([H])=C1[H]
0.000
abstract
2
HNJBEVLQSNELDL-UHFFFAOYSA-N
pyrrolidin-2-one
Chemical compound
O=C1CCCN1
HNJBEVLQSNELDL-UHFFFAOYSA-N
0.000
abstract
2
125000001424
substituent group
Chemical group
0.000
abstract
2
HUCDNALJLARZTQ-UHFFFAOYSA-N
3,4-dimethylazetidin-2-one
Chemical compound
CC1NC(=O)C1C
HUCDNALJLARZTQ-UHFFFAOYSA-N
0.000
abstract
1
ZEWHMWFASYXCAO-UHFFFAOYSA-N
4-ethenylazetidin-2-one
Chemical compound
C=CC1CC(=O)N1
ZEWHMWFASYXCAO-UHFFFAOYSA-N
0.000
abstract
1
MWKMQPSNTJCASD-UHFFFAOYSA-N
4-phenylazetidin-2-one
Chemical compound
N1C(=O)CC1C1=CC=CC=C1
MWKMQPSNTJCASD-UHFFFAOYSA-N
0.000
abstract
1
LVRCEUVOXCJYSV-UHFFFAOYSA-N
CN(C)S(=O)=O
Chemical group
CN(C)S(=O)=O
LVRCEUVOXCJYSV-UHFFFAOYSA-N
0.000
abstract
1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N
Diisopropyl ether
Chemical compound
CC(C)OC(C)C
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N
0.000
abstract
1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N
Dimethylsulphoxide
Chemical compound
CS(C)=O
IAZDPXIOMUYVGZ-UHFFFAOYSA-N
0.000
abstract
1
SECXISVLQFMRJM-UHFFFAOYSA-N
N-Methylpyrrolidone
Chemical compound
CN1CCCC1=O
SECXISVLQFMRJM-UHFFFAOYSA-N
0.000
abstract
1
229920002367
Polyisobutene
Polymers
0.000
abstract
1
239000000084
colloidal system
Substances
0.000
abstract
1
229960001760
dimethyl sulfoxide
Drugs
0.000
abstract
1
239000012442
inert solvent
Substances
0.000
abstract
1
239000007788
liquid
Substances
0.000
abstract
1
125000004433
nitrogen atom
Chemical group
N*
0.000
abstract
1
125000004430
oxygen atom
Chemical group
O*
0.000
abstract
1
239000003208
petroleum
Substances
0.000
abstract
1
238000006116
polymerization reaction
Methods
0.000
abstract
1
XAEFZNCEHLXOMS-UHFFFAOYSA-M
potassium benzoate
Chemical compound
[K+].[O-]C(=O)C1=CC=CC=C1
XAEFZNCEHLXOMS-UHFFFAOYSA-M
0.000
abstract
1
230000001681
protective effect
Effects
0.000
abstract
1
229920005604
random copolymer
Polymers
0.000
abstract
1
HXJUTPCZVOIRIF-UHFFFAOYSA-N
sulfolane
Chemical compound
O=S1(=O)CCCC1
HXJUTPCZVOIRIF-UHFFFAOYSA-N
0.000
abstract
1
239000002562
thickening agent
Substances
0.000
abstract
1
XLYOFNOQVPJJNP-UHFFFAOYSA-N
water
Substances
O
XLYOFNOQVPJJNP-UHFFFAOYSA-N
0.000
abstract
1
Classifications
C—CHEMISTRY; METALLURGY
C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
C08G69/14—Lactams
C08G69/22—Beta-lactams
Abstract
1,132,952. Block copolymers of #-lactams. FARBWERKE HOECHST A.G. 7 Jan., 1966 [7 Jan., 1965], No. 868/66. Heading C3R. Block copolymers of at least 2 #-lactams are produced by adding the lactams alternately to a solution or dispersion of a basic catalyst in an inert solvent. #-Lactams specified are those having unsubstituted nitrogen atoms and having up to 4 substituent groups on the α- and #- carbon atoms, these substituents containing up to a total of 12 aliphatic carbon atoms or 1 aromatic radical and up to a total of 9 aliphatic carbon atoms. They include 4-phenyl azetidinone, 4,4-dirnethyl-azetidinone, 4-vinyl-azetidinone, 4 – methyl – azetidinone, 4 – phenoxymethyl, 4-methyl-azetidinone and 3,4-dimethylazetidinone. Catalysts specified include: the potassium salt of α-pyrrolidone. Solvents specified include dimethyl sulphoxide, tetramethylene sulphone, dimethyl formamide, N-methyl pyrrolidone and mixtures thereof. Polymerization may occur at- 15 to +120 C., in the presence of an initiator which may be added to the catalyst solution before addition of the monomer or added with the monomer. Specified initiators include oxalyl pyrrolidone. A terminator, e.g. water, may also be added with the monomer. The invention may be used to prepare a copolymer of at least 2 #-lactams and a higher lactam, e.g. α-pyrrolidone. In a particular embodiment of the invention the catalyst solution or dispersion is in the form of an emulsion with another liquid which is a solvent for the lactam but only partially miscible with the catalyst solvent. The lactam solvent may be a C 5-24 aliphatic or cycloaliphatic hydrocarbon, an araliphatic hydrocarbon containing 1-3 benzene rings and 3-24 aliphatic carbon atoms, an aliphatic or araliphatic ether containing 1-3 ethereal oxygen atoms, 4-24 aliphatic carbon atoms and 0-3 benzene rings or a mixture thereof. Examples include diisopropyl ether and a heavy petroleum fraction. Emulsifiers, thickeners and protective colloids may be used to form the emulsion. A specified emulsifier is a dimethyl sulphonamide of an ethylene propylene copolymer having a repeating unit of formula In examples (1-4) a small quantity of one of the #-lactams is incorporated in the catalyst solution before the main addition is begun. In Example 2 a random copolymer of 2 #- lactams is prepared in addition to a block copolymer. In Example 3 a block copolymer of 3 #-lactams is prepared. In Example 4 the emulsion also contains polyisobutylene.
GB868/66A
1965-01-07
1966-01-07
Process for the manufacture of copolymers of -ß-lactams
Expired
GB1132952A
(en)
Applications Claiming Priority (1)
Application Number
Priority Date
Filing Date
Title
DEF0044891
1965-01-07
Publications (1)
Publication Number
Publication Date
GB1132952A
true
GB1132952A
(en)
1968-11-06
Family
ID=7100252
Family Applications (1)
Application Number
Title
Priority Date
Filing Date
GB868/66A
Expired
GB1132952A
(en)
1965-01-07
1966-01-07
Process for the manufacture of copolymers of -ß-lactams
Country Status (5)
Country
Link
US
(1)
US3417163A
(en)
BE
(1)
BE674844A
(en)
DE
(1)
DE1570531A1
(en)
FR
(1)
FR1463302A
(en)
GB
(1)
GB1132952A
(en)
Families Citing this family (2)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
US3538059A
(en)
*
1965-01-07
1970-11-03
Hoechst Ag
Process for making beta-lactam polymers
US3549580A
(en)
*
1967-11-21
1970-12-22
Hoechst Ag
Process for the manufacture of spinnable solutions of beta-polyamides
Family Cites Families (4)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
NL120303C
(en)
*
1958-06-14
GB884974A
(en)
*
1959-05-29
1961-12-20
Exxon Research Engineering Co
Block copolymers
DE1175434B
(en)
*
1959-12-05
1964-08-06
Hoechst Ag
Process for the production of linear polyamides from ª-aminocarboxylic acids
US3342783A
(en)
*
1962-04-06
1967-09-19
Hoechst Ag
Process for the manufacture of polyamides from alpha, alpha-dialkyl substituted beta-lactams
1965
1965-01-07
DE
DE19651570531
patent/DE1570531A1/en
active
Pending
1966
1966-01-06
US
US518998A
patent/US3417163A/en
not_active
Expired – Lifetime
1966-01-07
FR
FR45207A
patent/FR1463302A/en
not_active
Expired
1966-01-07
BE
BE674844D
patent/BE674844A/xx
unknown
1966-01-07
GB
GB868/66A
patent/GB1132952A/en
not_active
Expired
Also Published As
Publication number
Publication date
FR1463302A
(en)
1966-12-23
DE1570531A1
(en)
1970-01-29
BE674844A
(en)
1966-07-07
US3417163A
(en)
1968-12-17
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