US4167465A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Unsaturated hydantoin coagents
Assignee: BASF Corp
•
Filing: 1978-03-13
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Granted: 1979-09-11
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Expires: 1998-03-13
Abstract
Abstract Unsaturated hydantoin derivatives of the formula ##STR1## where R 1 and R 2 are alkyl, R 3 is vinyl, allyl, alkylene, substituted alkylene or polyvalent aralkyl, R 4 is vinyl or allyl and n is 1 to 3, are coagents for curing polymeric compositions to improve their physical, chemical and electrical properties. These coagents are particularly useful in crosslinking PVC, polyethylene, chlorinated polyethylene and poly(ethylene/vinyl acetate) compositions.
Inventors
- 👤 Hyman W. Zussman
- 👤 Martin Knell
- 👤 Martin Dexter
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 13:30
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/54; C07D233/66; C07D233/72; C07D233/74; C08; C08F; C08F291/00
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
131 words
A curable polymeric composition comprising, per 100 parts by weight of, an essentially saturated polymer or a mixture of said polymers capable of being cured at elevated temperature in the presence of 1 to 10 parts by weight of an organic peroxide or of being cured without peroxide by radiation at ambient temperature, and from 0.1 to 10 parts by weight of an unsaturated hydantoin of the formula selected from the group consisting of ##STR12## wherein R 1 and R 2 are independently each hydrogen, alkyl of 1 to 6 carbon atoms or phenyl, or R 1 and R 2 together are alkylene of 4 to 6 carbon atoms, R 3 ' is alkylene of 1 to 6 carbon atoms, 3-oxapentamethylene, 2-allyloxytrimethylene or p-xylylene, and R 4 is vinyl or allyl.
Claim 2
Dependent Claim
131 words
A curable polymeric composition comprising, per 100 parts by weight of, an essentially saturated polymer or a mixture of said polymers capable of being cured at elevated temperature in the presence of 1 to 10 parts by weight of an organic peroxide or of being cured without peroxide by radiation at ambient temperature, and from 0.1 to 10 parts by weight of an unsaturated hydantoin of the formula selected from the group consisting of ##STR12## wherein R 1 and R 2 are independently each hydrogen, alkyl of 1 to 6 carbon atoms or phenyl, or R 1 and R 2 together are alkylene of 4 to 6 carbon atoms, R 3 ' is alkylene of 1 to 6 carbon atoms, 3-oxapentamethylene, 2-allyloxytrimethylene or p-xylylene, and R 4 is vinyl or allyl.
Claim 3
Dependent Claim
56 words
A composition according to claim 1 wherein in the hydantoin compound R 1 and R 2 are independently each alkyl of 1 to 4 carbon atoms, or R 1 and R 2 together are pentamethylene; R 3 ' is alkylene of 1 to 2 carbon atoms, 2-allyloxytrimethylene or p-xylylene and R 4 is vinyl or allyl.
Claim 4
Dependent Claim
19 words
A composition according to claim 1 where in the hydantoin compound R 1 and R 2 are each methyl.
Claim 5
Dependent Claim
12 words
A composition according to claim 1 wherein the hydantoin compound is 1,3-diallyl-5,5-dimethylhydantoin.
Claim 6
Dependent Claim
12 words
A composition according to claim 1 wherein the hydantoin compound is 1,1'-methylene-bis(3-allyl-5,5-dimethylhydantoin).
Claim 7
Dependent Claim
12 words
A composition according to claim 1 wherein the hydantoin compound is 1,1'-p-xylylene-bis(3-vinyl-5,5-dimethylhydantoin).
Claim 8
Dependent Claim
24 words
A composition according to claim 1 wherein 3 to 5 parts by weight of a compound according to formula I or II is used.
Claim 9
Dependent Claim
28 words
A composition according to claim 1 wherein the organic peroxide is selected from the group consisting of aryl peroxides, acyl peroxides, aralkyl peroxides, alkyl peroxides and ketone peroxides.
Claim 10
Dependent Claim
18 words
A composition according to claim 8 wherein 1.5 to 5 parts by weight of organic peroxide is used.
Claim 11
Dependent Claim
13 words
A composition according to claim 8 wherein the organic peroxide is dicumyl peroxide.
Claim 12
Dependent Claim
19 words
A composition according to claim 1 curable by radiation from γ-rays from the radioisotope cobalt-60 or from high-energy electrons.
Claim 13
Dependent Claim
12 words
A composition according to claim 11 curable by radiation from high-energy electrons.
Claim 14
Dependent Claim
43 words
A composition according to claim 1 wherein the essentially saturated polymer or mixture of said polymers is selected from the group consisting of the polymonoolefins; copolymers of monoolefins with other monoolefins, vinyl acetate or vinyl chloride; chlorinated polyethylene; chlorosulfonated polyethylene; and poly(vinyl chloride).
Claim 15
Dependent Claim
31 words
A composition according to claim 13 wherein the essentially saturated polymer or mixture of said polymers is selected from the group consisting of poly(vinyl chloride), chlorinated polyethylene and ethylene/vinyl acetate copolymer.
Claim 16
Dependent Claim
121 words
A process for curing an essentially saturated polymer or a mixture of such polymers which comprises incorporating into said polymer or mixture of said polymers for each 100 parts by weight of polymer 0 to 10 parts by weight of an organic peroxide, and from 0.1 to 10 parts by weight of an unsaturated hydantoin of the formula selected from the group consisting of ##STR13## wherein R 1 and R 2 are independently each hydrogen, alkyl of 1 to 6 carbon atoms or phenyl, or R 1 or R 2 together are alkylene of 4 to 6 carbon atoms, R 3 ' is alkylene of 1 to 6 carbon atoms, 3-oxapentamethylene, 2-allyloxytrimethylene or p-xylylene, and R 4 is vinyl or allyl.
Claim 17
Dependent Claim
121 words
A process for curing an essentially saturated polymer or a mixture of such polymers which comprises incorporating into said polymer or mixture of said polymers for each 100 parts by weight of polymer 0 to 10 parts by weight of an organic peroxide, and from 0.1 to 10 parts by weight of an unsaturated hydantoin of the formula selected from the group consisting of ##STR13## wherein R 1 and R 2 are independently each hydrogen, alkyl of 1 to 6 carbon atoms or phenyl, or R 1 or R 2 together are alkylene of 4 to 6 carbon atoms, R 3 ' is alkylene of 1 to 6 carbon atoms, 3-oxapentamethylene, 2-allyloxytrimethylene or p-xylylene, and R 4 is vinyl or allyl.
Claim 18
Dependent Claim
56 words
A process according to claim 15 where in the hydantoin compound R 1 and R 2 are independently each alkyl of 1 to 4 carbon atoms or R 1 and R 2 together are pentamethylene; R 3 ' is alkylene of 1 to 2 carbon atoms, 2-allyloxytrimethylene or p-xylylene, and R 4 is vinyl or allyl.
Claim 19
Dependent Claim
19 words
A process according to claim 15 where in the hydantoin compound R 1 and R 2 are each methyl.
Claim 20
Dependent Claim
12 words
A process according to claim 15 wherein the hydantoin compound is 1,3-diallyl-5,5-dimethylhydantoin.
Claim 21
Dependent Claim
12 words
A process according to claim 15 wherein the hydantoin compound is 1,1'-methylene-bis(3-allyl-5,5-dimethylhydantoin).
Claim 22
Dependent Claim
12 words
A process according to claim 15 wherein the hydantoin compound is 1,1'-p-xylylene-bis(3-vinyl-5,5-dimethylhydantoin).
Claim 23
Dependent Claim
24 words
A process according to claim 15 wherein 3 to 5 parts by weight of a compound according to formula I or II is used.
Claim 24
Dependent Claim
28 words
A process according to claim 15 wherein the organic peroxide is selected from the group consisting of aryl peroxides, acyl peroxides, aralkyl peroxides, alkyl peroxides and ketone peroxides.
Claim 25
Dependent Claim
18 words
A process according to claim 22 wherein 1.5 to 5 parts by weight of organic peroxide is used.
Claim 26
Dependent Claim
13 words
A process according to claim 22 wherein the organic peroxide is dicumyl peroxide.
Claim 27
Dependent Claim
22 words
A process according to claim 15 when curing is done by radiation from γ-rays from the radioisotope cobalt-60 or from high-energy electrons.
Claim 28
Dependent Claim
15 words
A process according to claim 25 when curing is done by radiation from high-energy electrons.
Claim 29
Dependent Claim
47 words
A composition prepared according to the process of claim 15 wherein the essentially saturated polymer or mixture of said polymers is selected from the group consisting of the polymonoolefins; copolymers of monoolefins with other monoolefins, vinyl acetate or vinyl chloride; chlorinated polyethylene; chlorosulfonated polyethylene; and poly(vinyl chloride).
Claim 30
Dependent Claim
31 words
A composition according to claim 27 wherein the essentially saturated polymer or mixture of said polymers is selected from the group consisting of poly(vinyl chloride), chlorinated polyethylene and ethylene/vinyl acetate copolymer.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-09-10 | 1983-03-12 | 1983-09-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-09-10 | 1987-03-12 | 1987-09-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-09-10 | 1991-03-12 | 1991-09-11 | $7700.00 | Window Closed / Lapsed |