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US 4,762,870 AGranted
Rubber compositions modified with hydroxy-benz-imidazole oxides
AssigneeThe Firestone Tire & Rubber Company
InventorsDaniel F. Graves, Hans-Wilhelm Engels
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AssigneeThe Firestone Tire & Rubber Company
InventorsDaniel F. Graves, Hans-Wilhelm Engels
Estimating the term…
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.
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.
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.
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.
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.
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.
Dependencies are inferred from the claim text.