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US4762870A
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Rubber compositions modified with hydroxy-benz-imidazole oxides
Assignee: Bridgestone Firestone Inc
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Filing: 1987-04-13
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Granted: 1988-08-09
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Expires: 2007-04-13
Abstract
Abstract It now has been found that the properties of rubber compositions comprising rubbers having an unsaturated carbon chain can be improved by including therein, a minor property-improving amount of at least one hydroxy-benzimidazole oxide compound of the formula ##STR1## wherein R is hydrogen, or a halogen, hydroxyl, lower acyl, lower hydrocarbyl, lower hydrocarbyloxy, lower hydrocarbylthio, carboxyl, cyano, amino, amide or --C(O)-- lower hydrocarbyl group, and R' is hydrogen, or a lower hydrocarbyl, lower hydrocarbyl amide, carboxamide carboxy acid, carboxy ester, or aryl group. When vulcanizates are prepared from such rubber compositions containing one or more fillers, the vulcanizates exhibit reduced low strain hysteresis and a high electrical resistivity. In another aspect of the invention, a filled vulcanizate made by vulcanizing uncured compositions of the type described above and containing a filler, particularly carbon black, is improved in filler interaction, hysteresis, modulus, compression set and resiliency. Rubber articles and portions thereof such as tires, hoses, springs, belts, treads, sidewalls and the like can be made utilizing the improved filled vulcanizates of the invention.
Inventors
- 👤 Daniel F. Graves
- 👤 Hans-Wilhelm Engels
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 05:18
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3442; C08K5/3445; C08K5/3447
Claims Analysis
Total Claims: 33
Claim 1
Independent Claim
72 words
A rubber composition comprising at least one rubber having an unsaturated carbon chain and a minor property-improving amount of at least one 1-hydroxy-benzimidazole 3-oxide compound of the formula ##STR11## wherein R is hydrogen, or a, hydroxyl, lower acyl, lower hydrocarbyl, lower hydrocarbyloxy, lower hydrocarbylthio, carboxyl, cyano, amino, amide or --C(O)-- lower hydrocarbyl group, and R' is hydrogen, or a lower hydrocarbyl, lower hydrocarbyl amide, carboxamide carboxy acid, carboxy ester, or aryl group.
Claim 2
Dependent Claim
72 words
A rubber composition comprising at least one rubber having an unsaturated carbon chain and a minor property-improving amount of at least one 1-hydroxy-benzimidazole 3-oxide compound of the formula ##STR11## wherein R is hydrogen, or a, hydroxyl, lower acyl, lower hydrocarbyl, lower hydrocarbyloxy, lower hydrocarbylthio, carboxyl, cyano, amino, amide or --C(O)-- lower hydrocarbyl group, and R' is hydrogen, or a lower hydrocarbyl, lower hydrocarbyl amide, carboxamide carboxy acid, carboxy ester, or aryl group.
Claim 3
Dependent Claim
27 words
The rubber composition of claim 1 wherein the rubber is NR, IR, BR, SBR, CR, CIIR, NIR or a mixture of two or more of said rubbers.
Claim 4
Dependent Claim
28 words
The rubber composition of claim 1 wherein the rubber is NR, SBR or a mixture containing at least about 50% of one of these, and R' is methyl.
Claim 5
Dependent Claim
13 words
The rubber composition of claim 1 wherein R is hydrogen, methyl, or methoxy.
Claim 6
Dependent Claim
16 words
The rubber composition of claim 1 wherein the rubber is an uncured or vulcanized rubber composition.
Claim 7
Dependent Claim
15 words
The rubber composition of claim 1 wherein R' is hydrogen or a lower alkyl group.
Claim 8
Dependent Claim
16 words
The rubber composition of claim 1 wherein R is hydrogen and R' is methyl or phenyl.
Claim 9
Dependent Claim
13 words
The rubber composition of claim 1 also containing at least one reinforcing filler.
Claim 10
Dependent Claim
14 words
The rubber composition of claim 1 also containing at least one carbon black filler.
Claim 11
Dependent Claim
87 words
A rubber composition comprising at least one rubber having an unsaturated carbon chain and a minor property-improving amount of at least one nitrogen- and oxygen-containing composition obtained by the reaction of a primary nitroalkane, a beta-ketosulfone, an alpha-sulfonyl carboxylic ester, an alpha-sulfonyl carboxamide with a benzofurazan oxide in the presence of an alkali, said benzofurazan oxide being characterized by the formula ##STR12## wherein R is hydrogen, or a, hydroxyl, lower acyl, lower hydrocarbyl, halohydrocarbyl lower hydrocarbyloxy, lower hydrocarbylthio, carboxyl, cyano, amino, amide or --C(O)-- lower hydrocarbyl group.
Claim 12
Dependent Claim
87 words
A rubber composition comprising at least one rubber having an unsaturated carbon chain and a minor property-improving amount of at least one nitrogen- and oxygen-containing composition obtained by the reaction of a primary nitroalkane, a beta-ketosulfone, an alpha-sulfonyl carboxylic ester, an alpha-sulfonyl carboxamide with a benzofurazan oxide in the presence of an alkali, said benzofurazan oxide being characterized by the formula ##STR12## wherein R is hydrogen, or a, hydroxyl, lower acyl, lower hydrocarbyl, halohydrocarbyl lower hydrocarbyloxy, lower hydrocarbylthio, carboxyl, cyano, amino, amide or --C(O)-- lower hydrocarbyl group.
Claim 13
Dependent Claim
27 words
The rubber composition of claim 10 wherein the rubber is NR, IR, BR, SBR, CR, CIIR, NIR or a mixture of two or more of said rubbers.
Claim 14
Dependent Claim
24 words
The rubber composition of claim 10 wherein the rubber is NR, SBR or a mixture containing at least about 50% of one of these.
Claim 15
Dependent Claim
16 words
The rubber of claim 10 wherein the rubber composition is an uncured or vulcanized rubber composition.
Claim 16
Dependent Claim
13 words
The rubber composition of claim 10 wherein R is hydrogen, methyl, or methoxy.
Claim 17
Dependent Claim
29 words
The rubber composition of claim 10 wherein the primary nitroalkane of the formula R'CH.sub.2 NO.sub.2 wherein R' is hydrogen or a lower alkyl, hydrocarbyl amide or carboxylic ester group.
Claim 18
Dependent Claim
53 words
The rubber composition of claim 10 wherein the beta-ketosulfonyl group is of the formula PhSO.sub.2 CR'HC(O)Ph wherein R' is hydrogen or a lower hydrocarbyl group, and the alpha-sulfonyl carboxylic acid ester and carboxamide are of the formula PhSO.sub.2 CH.sub.2 R' wherein R' is an amide, substituted amide, a carboxylic acid or carboxylic ester.
Claim 19
Dependent Claim
13 words
The rubber composition of claim 10 also containing at least one reinforcing filler.
Claim 20
Dependent Claim
14 words
The rubber composition of claim 11 also containing at least one carbon black filler.
Claim 21
Dependent Claim
80 words
A filled vulcanizate of a rubber composition comprising at least one rubber having an unsaturated carbon chain, a minor property-improving amount of at least one 1-hydroxy-benzimidazole-3-oxide compound of the formula ##STR13## wherein R is hydrogen, or a halogen, hydroxyl, lower acyl, lower hydrocarbyl, lower hydrocarbyloxy, lower hydrocarbylthio, carboxyl, cyano, amino, amide or --C(O)-- lower hydrocarbyl group, and R' is hydrogen, or a lower hydrocarbyl, lower hydrocarbyl amide, carboxamide carboxy acid, carboxy ester, or aryl group and at least one filler.
Claim 22
Dependent Claim
80 words
A filled vulcanizate of a rubber composition comprising at least one rubber having an unsaturated carbon chain, a minor property-improving amount of at least one 1-hydroxy-benzimidazole-3-oxide compound of the formula ##STR13## wherein R is hydrogen, or a halogen, hydroxyl, lower acyl, lower hydrocarbyl, lower hydrocarbyloxy, lower hydrocarbylthio, carboxyl, cyano, amino, amide or --C(O)-- lower hydrocarbyl group, and R' is hydrogen, or a lower hydrocarbyl, lower hydrocarbyl amide, carboxamide carboxy acid, carboxy ester, or aryl group and at least one filler.
Claim 23
Dependent Claim
32 words
The vulcanizate of claim 19 wherein the rubber is NR, SBR or a mixture containing at least about 50% SBR, and the filler is carbon black, silica or a mixture of these.
Claim 24
Dependent Claim
15 words
The vulcanizate of claim 19 wherein the filler is at least one reinforcing carbon black.
Claim 25
Dependent Claim
9 words
The vulcanizate of claim 19 wherein R' is methyl.
Claim 26
Dependent Claim
13 words
The vulcanizate of claim 19 wherein R is hydrogen and R' is methyl.
Claim 27
Dependent Claim
19 words
The rubber composition of claim 10 wherein the rubber composition is a filled vulcanizate containing at least one filler.
Claim 28
Dependent Claim
15 words
The filled vulcanizate of claim 24 wherein the filler is at least one carbon black.
Claim 29
Dependent Claim
79 words
A rubber composition comprising at least one rubber having an unsaturated carbon chain and from about 0.01 to about 5 parts by weight phr of at least one 1-hydroxybenzimidazole 3-oxide compound of the formula ##STR14## wherein R is hydrogen, or a halogen, hydroxyl, lower acyl, lower hydrocarbyl, lower hydrocarbyloxy, lower hydrocarbylthio, carboxyl, cyano, amino, amide or --C(O)-- lower hydrocarbyl group, and R' is hydrogen, or a lower hydrocarbyl, lower hydrocarbyl amide, carboxamide carboxy acid, carboxy ester, or aryl group.
Claim 30
Dependent Claim
79 words
A rubber composition comprising at least one rubber having an unsaturated carbon chain and from about 0.01 to about 5 parts by weight phr of at least one 1-hydroxybenzimidazole 3-oxide compound of the formula ##STR14## wherein R is hydrogen, or a halogen, hydroxyl, lower acyl, lower hydrocarbyl, lower hydrocarbyloxy, lower hydrocarbylthio, carboxyl, cyano, amino, amide or --C(O)-- lower hydrocarbyl group, and R' is hydrogen, or a lower hydrocarbyl, lower hydrocarbyl amide, carboxamide carboxy acid, carboxy ester, or aryl group.
Claim 31
Dependent Claim
94 words
A rubber composition comprising at least one rubber having an unsaturated carbon chain and from about 0.01 to about 5 parts by weight phr of at least one nitrogen- and oxygen-containing composition obtained by the reaction of a primary nitroalkane, a beta-ketosulfone, an alpha-sulfonyl carboxylic ester, an alpha-sulfonyl carboxamide with a benzofurazan oxide in the presence of an alkali, said benzofurazan oxide being characterized by the formula ##STR15## wherein R is hydrogen, or a halogen, hydroxyl, lower acyl, lower hydrocarbyl, halohydrocarbyl lower hydrocarbyloxy, lower hydrocarbylthio, carboxyl, cyano, amino, amide or --C(O)-- lower hydrocarbyl group.
Claim 32
Dependent Claim
94 words
A rubber composition comprising at least one rubber having an unsaturated carbon chain and from about 0.01 to about 5 parts by weight phr of at least one nitrogen- and oxygen-containing composition obtained by the reaction of a primary nitroalkane, a beta-ketosulfone, an alpha-sulfonyl carboxylic ester, an alpha-sulfonyl carboxamide with a benzofurazan oxide in the presence of an alkali, said benzofurazan oxide being characterized by the formula ##STR15## wherein R is hydrogen, or a halogen, hydroxyl, lower acyl, lower hydrocarbyl, halohydrocarbyl lower hydrocarbyloxy, lower hydrocarbylthio, carboxyl, cyano, amino, amide or --C(O)-- lower hydrocarbyl group.
Claim 33
Dependent Claim
24 words
The vulcanizate of claim 19 wherein the rubber composition contains from about 0.01 to about 5 parts by weight phr of the benzimidazole-3-oxide compound.
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) | 1991-08-09 | 1992-02-08 | 1992-08-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-08-09 | 1996-02-08 | 1996-08-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-08-09 | 2000-02-08 | 2000-08-09 | $7700.00 | Window Closed / Lapsed |