Rubber compositions modified with heterocyclic di-n-oxides

Details Rubber compositions modified with heterocyclic di-n-oxides Rubber compositions modified with heterocyclic di-n-oxides

C - Chemistry, Metallurgy

08

K

6/123, 400/4905,

C08K 5/34 (2006.01) C07D 241/52 (2006.01) C08K 5/3465 (2006.01) C08L 21/00 (2006.01)

Patent

CA 1307068

-57- Title: RUBBER COMPOSITIONS MODIFIED WITH HETEROCYCLIC DI-N-OXIDES ABSTRACT OF THE DISCLOSURE It now has been found that uncured rubber composition comprising rubbers having an unsaturated carbon chain and at least one carbon black can be improved by including therein, a minor property-improv- ing amount of at least one aromatic heterocyclic di-N- oxide compound of the partial formula Image (I) wherein the depicted carbon atoms are part of an option- ally substituted aromatic ring, and R1 and R2 are each independently hydrogen, hydrocarbyl, halohydrocar- byl, hydrocarbyloxy, hydrocarbyl sulfonyl, hydrocarbyl thio, hydrocarbylsulfoxidyl, halogen, amino, -CN -OH -CHO -CH(O hydrocarbyl)2 -C(O)R3 -C(O)OR3 -C(N-OH)R3 -C(O)NR3R6 -58- -CH=N-NH-C(O)OR3 -CH2OC(O)CH3 -R4YR3 -C(O)NHR4OH -C(NH)NR7R8, or -C(O)NHN(R3)2 wherein each R3 is independently hydrogen or a hydro- carbyl group, R4 is a divalent hydrocarbyl group, R6 is hydrogen, hydrocarbyl, -R4OR3, or -R4COOR3; R7 is hydrogen or a hydrocarbyl group; R8 is hydro- gen or a hydrocarbyl, an amino, or a hydroxyl group; R7 and R8 may be hydrocarbyl groups joined together to form a ring including the nitrogen atom, and Y is O, divalent S, -NH-, -S(O)- or -S(O)2 or R1 and R2 may be joined together to form further ring systems which may be saturated or unsaturated, and further substituted or unsubstituted. When vulcanizates are prepared from such uncured rubber compositions, parti- cularly when the carbon black used therein has an average surface area of at least about 20 m2/g, the vulcanizates exhibit reduced low strain hysteresis and exhibit no significant undesirable odor. 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 made from such vulcanizates such as tires, hoses, belts, springs, treads, sidewalls and the like can be made utilizing the improved filled vulcanizates of the invention.

563932

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