US3972961A
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Process for the preparation of graft copolymers
Assignee: EIDP Inc
•
Filing: 1974-11-13
•
Granted: 1976-08-03
•
Expires: 1994-11-13
Abstract
Abstract Process for the preparation of thermoplastic graft copolymers which comprises heating for about 15 seconds to 60 minutes, with mixing, a trunk copolymer of at least two monomers, at least one of said monomers providing amine-reactive sites taken from the group consisting of the anhydride group, e.g., maleic anhydride; a vicinal pair of carboxylic groups and a carboxylic acid adjacent to an alkoxycarbonyl group, wherein the alkoxy group contains up to 20 carbon atoms, and at least one of said monomers containing no amine-reactive sites, and at least one side chain polymer having per chain one active amine site taken from the group consisting of primary and secondary amines, the remainder of said side chain polymer being substantially unreactive with the reactive sites, e.g., amino-substituted polycaprolactam, polylaurolactam, polyethylene oxide, etc., of the trunk copolymer. The process provides control of the type and length of the side chain polymer grafted onto the trunk copolymer. Plastic graft copolymers are included, specifically those containing one or more side chain polymer types with the proviso that when only one type side chain polymer is present the side chain polymer contains only one nitrogen atom, said atom being found in the active amine site.
Inventors
- 👤 Clarence Frederick Hammer
- 👤 Harold King Sinclair
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 14:24
CPC Classifications
C; C08; C08G; C08G81/00; C08G81/02
Claims Analysis
Total Claims: 69
Claim 1
Independent Claim
136 words
Process for the preparation of thermoplastic graft copolymers which comprises heating for about 15 seconds to 60 minutes, with mixing, (1) a trunk copolymer of at least two monomers, at least one of said monomers providing amine-reactive sites taken from the group consisting of an anhydride group, a vicinal pair of carboxylic groups and a carboxylic group adjacent to an alkoxycarbonyl group, wherein the alkoxy group contains up to 20 carbon atoms, and at least one of said monomers containing no aminereactive sites, and (2) at least one side chain polymer, ranging in length from about 25 to 1000 chain atoms, having per chain one active amine site taken from the group consisting of primary and secondary amines, the remainder of said side chain polymer being substantially unreactive with the reactive sites of the trunk copolymer.
Claim 2
Dependent Claim
136 words
Process for the preparation of thermoplastic graft copolymers which comprises heating for about 15 seconds to 60 minutes, with mixing, (1) a trunk copolymer of at least two monomers, at least one of said monomers providing amine-reactive sites taken from the group consisting of an anhydride group, a vicinal pair of carboxylic groups and a carboxylic group adjacent to an alkoxycarbonyl group, wherein the alkoxy group contains up to 20 carbon atoms, and at least one of said monomers containing no aminereactive sites, and (2) at least one side chain polymer, ranging in length from about 25 to 1000 chain atoms, having per chain one active amine site taken from the group consisting of primary and secondary amines, the remainder of said side chain polymer being substantially unreactive with the reactive sites of the trunk copolymer.
Claim 3
Dependent Claim
20 words
A process according to claim 1 wherein the active amine site of the side chain polymer is a primary amine.
Claim 4
Dependent Claim
14 words
A process according to claim 1 wherein the process is conducted in the melt.
Claim 5
Dependent Claim
13 words
A process according to claim 1 wherein the process is conducted in solution.
Claim 6
Dependent Claim
23 words
A process according to claim 1 wherein the heating temperature is above the melting points of the trunk copolymer and side chain polymer.
Claim 7
Dependent Claim
18 words
A process according to claim 1 wherein the heating is conducted for about 15 seconds to 10 minutes.
Claim 8
Dependent Claim
36 words
A process according to claim 1 wherein the trunk copolymer is derived from an α-olefin and at least one monomer providing amine-reactive sites taken from the group consisting of an anhydride, diacid and half-esters derived therefrom.
Claim 9
Dependent Claim
11 words
A process according to claim 7 wherein the α-olefin is ethylene.
Claim 10
Dependent Claim
26 words
A process according to claim 8 wherein there is present at least one additional polymerizable monomer which contains no amine-reactive sites and no anhydride reactive sites.
Claim 11
Dependent Claim
13 words
A process according to claim 9 wherein the additional polymerizable monomer is 3-methylbutene.
Claim 12
Dependent Claim
14 words
A process according to claim 9 wherein the additional polymerizable monomer is vinyl acetate.
Claim 13
Dependent Claim
14 words
A process according to claim 9 wherein the additional polymerizable monomer is methyl acrylate.
Claim 14
Dependent Claim
14 words
A process according to claim 9 wherein the additional polymerizable monomer is methyl methacrylate.
Claim 15
Dependent Claim
35 words
A process according to claim 1 wherein the trunk copolymer is derived from styrene and at least one monomer providing amine-reactive sites taken from the group consisting of an anhydride, diacid and half-esters derived therefrom.
Claim 16
Dependent Claim
25 words
A process according to claim 14 wherein there is present at least one additional polymerizable monomer containing no amine-reactive sites and no anhydride reactive sites.
Claim 17
Dependent Claim
31 words
A process according to claim 7 wherein the monomer providing amine-reactive sites is maleic anhydride wherein the maleic anhydride is present in an amount of 1.0 to 25.0 parts by weight.
Claim 18
Dependent Claim
31 words
A process according to claim 14 wherein the monomer providing amine-reactive sites is maleic anhydride wherein the maleic anhydride is present in an amount of 1.0 to 30.0 parts by weight.
Claim 19
Dependent Claim
35 words
A process according to claim 9 wherein the trunk copolymer is composed of ethylene, monoalkyl maleate, wherein alkyl is in the range of 1 to 4 carbon atoms, in addition to an additional polymerizable monomer.
Claim 20
Dependent Claim
35 words
A process according to claim 9 wherein the trunk copolymer is composed of ethylene, monoalkyl fumarate wherein alkyl is in the range of 1 to 4 carbon atoms, in addition to an additional polymerizable monomer.
Claim 21
Dependent Claim
35 words
A process according to claim 9 wherein the trunk copolymer is composed of ethylene, monoalkyl itaconate wherein alkyl is in the range of 1 to 4 carbon atoms, in addition to an additional polymerizable monomer.
Claim 22
Dependent Claim
84 words
A process according to claim 1 wherein the side chain polymer is selected from the group consisting of polymers of lactams containing 3 to 12 carbon atoms, copolymers of lactams containing 3 to 12 carbon atoms, polymers of organic oxides containing 2 to 16 carbon atoms, copolymers of organic oxides containing 2 to 16 carbon atoms, polymers of styrene, polymers of substituted styrenes, copolymers of styrene and substituted styrene, polymers of acrylates, polymers of methacrylates, copolymers of acrylates and methacrylates, and polymers of lactones.
Claim 23
Dependent Claim
15 words
A process according to claim 21 wherein a side chain polymer present is a polycaprolactam.
Claim 24
Dependent Claim
15 words
A process according to claim 21 wherein a side chain polymer present is a polylaurolactam.
Claim 25
Dependent Claim
19 words
A process according to claim 21 wherein a side chain polymer present is a copolymer of caprolactam and laurolactam.
Claim 26
Dependent Claim
15 words
A process according to claim 21 wherein a side chain polymer present is polyethylene oxide.
Claim 27
Dependent Claim
15 words
A process according to claim 21 wherein a side chain polymer present is polypropylene oxide.
Claim 28
Dependent Claim
14 words
A process according to claim 21 wherein a side chain polymer present is polystyrene.
Claim 29
Dependent Claim
57 words
A process according to claim 21 wherein the side chain polymers are short chains having repeat units from about 5 to 50 in which at least 80 percent of the side chain polymers have one active amine site and the remainder of said side chain polymer is substantially unreactive with the amine-reactive sites on the trunk copolymer.
Claim 30
Dependent Claim
21 words
A process according to claim 28 wherein the side chain polymers contain substituent alkyl groups of 1 to 18 carbon atoms.
Claim 31
Dependent Claim
15 words
A process according to claim 28 wherein the side chain polymers contain substituent aryl groups.
Claim 32
Dependent Claim
46 words
A process according to claim 1 wherein the trunk copolymers contain, on the average, about 300 to 50,000 chain atoms and the number of reactive sites occur, on the average, at a frequency of 1 to 50 sites per thousand chain atoms of the main chain.
Claim 33
Dependent Claim
23 words
A process according to claim 31 wherein trunk copolymers contain, on the average, about 500 to 2,000 chain atoms of the main chain.
Claim 34
Dependent Claim
29 words
A process according to claim 31 wherein the side chain polymer reactive with the amine-reactive sites on the trunk copolymer range in length from 25 to 1,000 chain atoms.
Claim 35
Dependent Claim
173 words
A thermoplastic graft copolymer consisting essentially of a trunk copolymer derived from at least two monomers, at least one of said monomers providing amine-reactive sites selected from the group consisting of an anhydride group, a vicinal pair of carboxylic groups and a carboxylic group adjacent to an alkoxycarbonyl group, wherein the alkoxy group contains up to 20 carbon atoms, and at least one of said monomers containing no amine-reactive sites; and at least one type side chain polymer linked to said reactive sites through amide or imide linkages, said side chain polymer being derived from a short chain polymer having from about 5 to 50 repeat units and containing one active amine site selected from the group consisting of primary and secondary amines, the remainder of the side chain polymer being substantially unreactive with the amine-reactive sites of the trunk copolymer, with the proviso that when only one type of side chain polymer is present the side chain polymer contains only one nitrogen atom, said atom being found in the active amine site.
Claim 36
Dependent Claim
173 words
A thermoplastic graft copolymer consisting essentially of a trunk copolymer derived from at least two monomers, at least one of said monomers providing amine-reactive sites selected from the group consisting of an anhydride group, a vicinal pair of carboxylic groups and a carboxylic group adjacent to an alkoxycarbonyl group, wherein the alkoxy group contains up to 20 carbon atoms, and at least one of said monomers containing no amine-reactive sites; and at least one type side chain polymer linked to said reactive sites through amide or imide linkages, said side chain polymer being derived from a short chain polymer having from about 5 to 50 repeat units and containing one active amine site selected from the group consisting of primary and secondary amines, the remainder of the side chain polymer being substantially unreactive with the amine-reactive sites of the trunk copolymer, with the proviso that when only one type of side chain polymer is present the side chain polymer contains only one nitrogen atom, said atom being found in the active amine site.
Claim 37
Dependent Claim
20 words
A graft copolymer according to claim 34 wherein the trunk copolymer and side chain polymers are linked through imide linkages.
Claim 38
Dependent Claim
80 words
A graft copolymer according to claim 34 wherein solely one type of side chain polymer is linked to the trunk copolymer, said side chain polymer being selected from the group consisting of polymers of organic oxides containing 2 to 16 carbon atoms, copolymers of organic oxides containing 2 to 16 carbon atoms, polymers of styrene, polymers of substituted styrenes, copolymers of styrene and substituted styrene, polymers of acrylates, polymers of methacrylates, copolymers of acrylates and methacrylates, and polymers of lactones.
Claim 39
Dependent Claim
15 words
A graft copolymer according to claim 36 wherein the side chain polymer is polyethylene oxide.
Claim 40
Dependent Claim
15 words
A graft copolymer according to claim 36 wherein the side chain polymer is polypropylene oxide.
Claim 41
Dependent Claim
15 words
A graft copolymer according to claim 36 wherein the side chain polymer is a polymethacrylate.
Claim 42
Dependent Claim
15 words
A graft copolymer according to claim 36 wherein the side chain polymer is a polyacrylate.
Claim 43
Dependent Claim
14 words
A graft copolymer according to claim 36 wherein the side chain polymer is polystyrene.
Claim 44
Dependent Claim
18 words
A graft copolymer according to claim 34 wherein at least two different type side chain polymers are present.
Claim 45
Dependent Claim
85 words
A graft copolymer according to claim 42 wherein the side chain polymers are selected from the group consisting of polymers of lactams containing 3 to 12 carbon atoms, copolymers of lactams containing 3 to 12 carbon atoms, polymers of organic oxides containing 2 to 16 carbon atoms, copolymers of organic oxides containing 2 to 16 carbon atoms, polymers of styrene, polymers of substituted styrenes, copolymers of styrene and substituted styrene, polymers of acrylates, polymers of methacrylates, copolymers of acrylates and methacrylates, and polymers of lactones.
Claim 46
Dependent Claim
17 words
A graft copolymer according to claim 43 wherein the side chain polymers are polyethylene oxide and polycaprolactam.
Claim 47
Dependent Claim
18 words
A graft copolymer according to claim 43 wherein the side chain polymers are polyethylene oxide and polymethyl methacrylate.
Claim 48
Dependent Claim
17 words
A graft copolymer according to claim 43 wherein the side chain polymers are polystyrene and polyethylene oxide.
Claim 49
Dependent Claim
17 words
A graft copolymer according to claim 43 wherein the side chain polymers are polystyrene and polymethyl methacrylate.
Claim 50
Dependent Claim
36 words
A graft copolymer according to claim 34 wherein the trunk copolymer is derived from ethylene and at least one monomer providing amine-reactive sites taken from the group consisting of an anhydride, diacid and half-esters derived therefrom.
Claim 51
Dependent Claim
27 words
A graft copolymer according to claim 48 wherein there is present at least one additional polymerizable monomer which contains no amine-reactive sites and no anhydride reactive sites.
Claim 52
Dependent Claim
14 words
A graft copolymer according to claim 48 wherein the side chain is polyethylene oxide.
Claim 53
Dependent Claim
25 words
A graft copolymer according to claim 48 wherein the side chain is a polymer selected from the group consisting of polyacrylate, polymethacrylate or copolymers thereof.
Claim 54
Dependent Claim
32 words
A graft copolymer according to claim 48 wherein the monomer providing amine-reactive sites is maleic anhydride wherein the maleic anhydride is present in an amount of 1.0 to 25 parts by weight.
Claim 55
Dependent Claim
36 words
A graft copolymer according to claim 34 wherein the trunk copolymer is derived from styrene and at least one monomer providing amine-reactive sites taken from the group consisting of an anhydride, diacid and half-esters derived therefrom.
Claim 56
Dependent Claim
26 words
A graft copolymer according to claim 53 wherein there is present at least one additional polymerizable monomer containing no amine-reactive sites and no anhydride reactive sites.
Claim 57
Dependent Claim
32 words
A graft copolymer according to claim 53 wherein the monomer providing amine-reactive sites is maleic anhydride wherein the maleic anhydride is present in an amount of 1.0 to 30 parts by weight.
Claim 58
Dependent Claim
36 words
A graft copolymer according to claim 49 wherein the trunk copolymer is composed of ethylene, monoalkyl maleate, wherein alkyl is in the range of 1 to 4 carbon atoms, in addition to an additional polymerizable monomer.
Claim 59
Dependent Claim
36 words
A graft copolymer according to claim 49 wherein the trunk copolymer is composed of ethylene, monoalkyl fumarate wherein alkyl is in the range of 1 to 4 carbon atoms, in addition to an additional polymerizable monomer.
Claim 60
Dependent Claim
36 words
A graft copolymer according to claim 49 wherein the trunk copolymer is composed of ethylene, monoalkyl itaconate wherein alkyl is in the range of 1 to 4 carbon atoms, in addition to an additional polymerizable monomer.
Claim 61
Dependent Claim
65 words
A graft copolymer according to claim 34 wherein the trunk copolymer contains, on a number average, about 300 to 50,000 chain atoms and the number of reactive sites occur, on the average, at a frequency of about 1 to 200 reactive sites per thousand chain atoms of the trunk copolymer, there being on the average at least about one active site per trunk copolymer chain.
Claim 62
Dependent Claim
21 words
A graft copolymer according to claim 59 wherein the trunk copolymer contains, on the average, about 500 to 2,000 chain atoms.
Claim 63
Dependent Claim
30 words
A graft copolymer according to claim 59 wherein any side chain polymer reactive with the amine-reactive sites on the trunk copolymer range in length from 25 to 1,000 chain atoms.
Claim 64
Dependent Claim
21 words
A process according to claim 1 wherein the side chain polymer has an average degree of polymerization of 5 to 60.
Claim 65
Dependent Claim
21 words
A process according to claim 62 wherein the average degree of polymerization of the side chain polymer is 6 to 8.
Claim 66
Dependent Claim
22 words
A graft copolymer according to claim 34 wherein the side chain polymer has an average degree of polymerization of 5 to 60.
Claim 67
Dependent Claim
22 words
A graft copolymer according to claim 64 wherein the average degree of polymerization of the side chain polymer is 6 to 8.
Claim 68
Dependent Claim
26 words
A graft copolymer according to claim 64 wherein the non-reactive end of the side chain polymer has substituent alkyl groups of 1 to 18 carbon atoms.
Claim 69
Dependent Claim
20 words
A graft copolymer according to claim 64 wherein the non-reactive end of the side chain polymer has substituent aryl groups.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-08-03 | 1980-02-02 | 1980-08-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-08-03 | 1984-02-02 | 1984-08-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-08-03 | 1988-02-02 | 1988-08-03 | $7700.00 | Window Closed / Lapsed |