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US4136077A
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Reaction product of olefinically-unsaturated nitrile and a monoolefinic hydrocarbon as plasticizer for conjugated diene-unsaturated nitrile rubber
Assignee: Phillips Petroleum Co
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Filing: 1977-12-16
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Granted: 1979-01-23
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Expires: 1997-12-16
Abstract
Abstract A reaction product of an olefinically unsaturated nitrile and a monoolefinic hydrocarbon containing an allylic hydrogen atom is used as plasticizer for a conjugated diene-unsaturated nitrile rubber.
Inventors
- 👤 Ralph P. Williams
- 👤 William S. Howard
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 22:02
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/315; C07; C07C; C07C255/00; C08L; C08L33/00; C08L33/18; C08L33/22; C08L9/00; C08L9/02; C08L101/00; C08L101/02
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
107 words
A conjugated diene-unsaturated nitrile rubber plasticized with at least one reaction product of an olefinically unsaturated nitrile, having the general formula (I) RCH═CR--CN and a monoolefinic hydrocarbon, containing an allylic hydrogen atom and represented by the formula (II) R' .sub.2 C═CR'CHR'--.sub.2, which have been thermally contacted to produce an unsaturated diadduct product having the formula ##STR3## wherein each R and each R' is independently selected from the group consisting of hydrogen and hydrocarbyl radicals, and an oligomer thereof, which can be represented by the formula ##STR4## wherein R and R' are as defined earlier and n is equal to an integer in the range 2 to 20.
Claim 2
Dependent Claim
107 words
A conjugated diene-unsaturated nitrile rubber plasticized with at least one reaction product of an olefinically unsaturated nitrile, having the general formula (I) RCH═CR--CN and a monoolefinic hydrocarbon, containing an allylic hydrogen atom and represented by the formula (II) R' .sub.2 C═CR'CHR'--.sub.2, which have been thermally contacted to produce an unsaturated diadduct product having the formula ##STR3## wherein each R and each R' is independently selected from the group consisting of hydrogen and hydrocarbyl radicals, and an oligomer thereof, which can be represented by the formula ##STR4## wherein R and R' are as defined earlier and n is equal to an integer in the range 2 to 20.
Claim 3
Dependent Claim
25 words
A composition according to claim 1 wherein R and R' are selected from the group consisting of alkyl, cycloalkyl, aryl hydrocarbyl radicals and combinations thereof.
Claim 4
Dependent Claim
32 words
A composition according to claim 2 wherein the nitrile is at least one selected from the acrylonitrile, methacrylonitrile, 2-decenenitrile, 3-cyclohexyl-2-propenenitrile, 4-phenyl-2-butenenitrile, 3-(p-tolyl)-2-propenenitrile, 2-butenenitrile, 2-hexenenitrile, 5-methyl-2-hexenenitrile, 4-methyl-2-heptenenitrile, 6,6,8,8,-tetramethyl-2-nonenenitrile, 6-cyclohexyl-2-octenenitrile, 6-phenyl-2-decenenitrile, 2-octadecenenitrile, 6,7,8-trimethyl-9-phenyl-2-nonenenitrile, 5-p-tolyl-2-nonenenitrile.
Claim 5
Dependent Claim
37 words
A composition according to claim 2 wherein in the olefinically unsaturated hydrocarbon is propylene, isobutylene, diisobutylene, 1,5-hexadiene, beta-pinene, 1,5-cyclooctadiene, 2,4,4-trimethyl-1-pentene, 2-butene, biallyl, bimethallyl, alpha-methyl-styrene, beta-methylstyrene, 1-pentene, 1-decene, cyclohexene, 1-allyl-cyclohexene, 3-allylcyclohexene, 4-allylcyclohexene, allylbenzene, 3,4,4-trimethyl-2-pentene, 1-dodecene, 2,3-dimethyl-2-butene, and 2-methyl-1-phenyl-2-propene.
Claim 6
Dependent Claim
25 words
A composition according to claim 1 wherein the rubber is butadiene-acrylonitrile rubber and the plasticizer is at least one reaction product of isobutylene and acrylonitrile.
Claim 7
Dependent Claim
23 words
A composition according to claim 1 wherein the plasticizer is at least one 5-methyl-4-nonenedinitrile and 5-methylene nonanedinitrile and corresponding isomers and oligomers thereof.
Claim 8
Dependent Claim
50 words
A composition according to claim 1 wherein the plasticizer is at least a portion of the oligomer kettle product obtained from the distillation of the reaction mass in which isobutylene and acrylonitrile have been reacted to produce unsaturated diadduct dinitriles, 5-methyl-4-nonenedinitrile and 5-methylene nonanedinitrile and corresponding isomers and oligomers thereof.
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) | 1982-01-22 | 1982-07-24 | 1983-01-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-01-22 | 1986-07-24 | 1987-01-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-01-22 | 1990-07-24 | 1991-01-23 | $7700.00 | Window Closed / Lapsed |