Cyclic diol-derived blocked mercaptofunctional silane compositions
View Patent ↗Diol derived blocked mercaptofunctional silane compositions in which the silanes comprise cyclic and bridged alkoxy groups derived from hydrocarbon-based diols and processes for their preparation are provided. Also provided are rubber compositions comprising the cyclic diol-derived blocked mercaptofunctional silanes, processes for their preparation and articles of manufacture comprising the rubber compositions, in particular, automotive tires and components thereof.
1. A rubber composition comprising (a) at least one rubber component, (b) at least one filler and (c) an effective amount of at least one cyclic and bridging dialkoxy silane composition comprising at least one component having a chemical structure selected from the group consisting of:
wherein:
each occurrence of the —SiX u Z b v Z c w group is independently selected from the group consisting of —SiXZ c , —SiZ b Z c , —SiX 2 Z b , —SiXZ b 2 and —SiZ b 3 ;
each occurrence of R is independently selected from the group consisting of hydrogen, straight, cyclic or branched alkyl group, alkenyl group, aryl group, and aralkyl group, with each R, other than hydrogen, containing from 1 to 18 carbon atoms;
each occurrence of G is independently selected from the group consisting of hydrogen, a monovalent alkyl, alkenyl, aryl or aralkyl group containing from 1 to 30 carbon atoms, and a polyvalent group containing from 1 to 30 carbon atoms derived by substitution of alkyl, alkenyl, aryl or aralkyl group;
each occurrence of X is independently selected from the group consisting of —Cl, —Br, R 1 O—, R 1 O(R 4 CR 5 ) f O—, R 1 C(═O)O—, R 1 R 2 C═NO—, R 1 R 2 NO—, R 1 R 2 N—, —R 1 , and —(OSi R 1 R 2 ) t (OSi R 1 R 2 R 3 ), wherein each occurrence of R 1 , R 2 and R 3 is independently R;
each occurrence of Z b , which forms a bridging structure between two different silicon atoms, is independently selected from the (—O—) 0.5 consisting of [—O(R 4 CR 5 ) f O—] 0.5 , wherein each occurrence of R 4 and R 5 is independently R;
each occurrence of Z c , which forms a cyclic structure with a single silicon atom, is independently given by —O(R 4 CR 5 ) f O— wherein each occurrence of R 4 and R 5 is independently R;
each occurrence of the subscripts, u, n, v, w, f, p, r, q, j, p, t, s, and k is independently given by u is 0 to 3; n is 1 to 100, with the proviso that when n is greater than 1, v is greater than 0 and all the valences for Z b have a silicon atom bonded to them; v is 0 to 3; w is 0 to 1 with the proviso that u+v+2w is 3; f is 1 to 15; p is 0 to 5; r is 1 to 3; q is 0 to 6; i is 0 to 1, with the proviso that when j is 0, p is 1; t is 0 to 50; s is 1 to 3; and k is 1, wherein each of the above structures comprise at least two hydrolysable bridging dialkoxy group, Z b , or at least one hydrolysable cyclic dialkoxy group, Z c .
2. The rubber composition of claim 1 , wherein the rubber component is at least one sulfur vulcanizable rubber selected from the group consisting of conjugated diene homopolymers and copolymers, copolymers of at least one conjugated diene and aromatic vinyl compound and mixtures thereof.
3. The rubber composition of claim 1 wherein the rubber component is selected from the group consisting of natural rubber, emulsion polymerization styrene/butadiene rubber, emulsion polymerization butadiene/acrylonitrile rubber, emulsion polymerization styrene/butadiene/acrylonitrile rubber, solvent polymerization styrene/butadiene rubber containing from about 25 to about 48 percent vinyl content and solvent polymerization styrene/butadiene rubber containing from about 53 to about 75 percent vinyl content.
4. The rubber composition according to claim 1 , wherein the cyclic and bridging dialkoxy silane is selected from the group consisting of 2-(2-methyl-2,4-pentanedialkoxyethoxysilyl)-1-ethyl thioacetate;
2-(2-methyl-2,4-pentanedialkoxymethoxysilyl)-1-ethyl thioacetate;
2-(2-methyl-2,4-pentanedialkoxy methylsilyl)-1-ethyl thioacetate;
3-(2-methyl-2,4-pentanedialkoxymethoxysilyl)-1-propyl thioacetate;
2-methyl-2,4-pentanedialkoxyethoxysilylmethyl thioacetate;
2-methyl-2,4-pentanedialkoxyisopropoxysilylmethyl thioacetate;
neopentylglycoxypropoxysilylmethyl thioacetate;
propyleneglycoxymethylsilylmethyl thioacetate;
neopentylglycoxyethylsilylmethyl thioacetate;
2-(neopentylglycoxyisopropoxysilyl)-1-ethyl thioacetate;
2-(neopentylglycoxy methylsilyl)-1-ethyl thioacetate;
2-(1,3-butanedialkoxymethylsilyl)-1-ethyl thioacetate;
3-(1,3-butanedialkoxyethoxysilyl)-1-propyl thioacetate;
3-(1,3-butanedialkoxyisopropoxysilyl)-4-butyl thioacetate;
3-(1,3-butanedialkoxyethylsilyl)-1-propyl thioacetate;
3-(1,3-butanedialkoxymethylsilyl)-1-propyl thioacetate;
6-(2-methyl-2,4-pentanedialkoxyethoxysilyl)-1-hexyl thioacetate;
1-(2-methyl-2,4-pentanedialkoxyethoxysilyl)-5-hexyl thioacetate;
8-(2-methyl-2,4-pentanalialkoxyethoxysilyl)-1-octyl thioacetate;
10-(2-methyl-2,4-pentanedialkoxyethoxysilyl)-1-decyl thioacetate;
3-(2-methyl-2,4-pentanedialkoxyethoxysilyl)-1-propyl thiooctanoate;
3-(2-methyl-2,4-pentanedialkoxyethoxysilyl)-1-propyl thiodecanoate;
3-(2-methyl-2,4-pentanedialkoxyethoxysilyl)-1-propyl thiododecanoate;
3-(2-methyl-2,4-pentanedialkoxyethoxysilyl)-1-propyl thio-2-ethylhexanoate;
3-(2-methyl-2,4-pentanedialkoxyethoxysilyl)-1-propyl thio-2-methylheptanoate;
bis-(3-(2-methyl-2,4-pentanedialkoxyethoxysilyl)-1-propyl)dithioadipate;
6-(1,3-butanedialkoxyethoxysilyl)-1-hexyl thioacetate;
1-(1,3-butanedialkoxyethoxysilyl)-5-hexyl thioacetate;
8-(1,3-butanedialkoxyethoxysilyl)-1-octyl thioacetate;
10-(1,3-butanedialkoxyethoxysilyl)-1-decyl thioacetate;
3-(1,3-butanedialkoxyethoxysilyl)-1-propyl thiooctanoate;
3-(1,3-butanedialkoxyethoxysilyl)-1-propyl thiodecanoate;
3-(1,3-butanedialkoxypropoxysilyl)-1-propyl thiododecanoate;
3-(2-methyl-2,4-pentanedialkoxyethoxysilyl)-1-propyl thio-2-ethylhexanoate;
3-(2-methyl-2,4-pentanedialkoxyethoxysilyl)-1-propyl thio-2-methylheptanoate;
3-(2-methyl-1,3-propanedialkoxyethoxysilyl)-1-propyl thiooctanoate;
3-(2-methyl-1,3-propanedialkoxyethoxysilyl)-1-propyl thiodecanoate;
3-(2,2-dimethyl-1,3-propanedialkoxyethoxysilyl)-1-propyl thiodecanoate;
3-(2,2-dimethyl-1,3-propanedialkoxyethoxysilyl)-1-propyl thiooctanoate;
3-(2-methyl-2,4-pentanedialkoxyethoxysilyl)-1-propyl thiooctanoate;
3-(2-methyl-2,4-pentanedialkoxyethoxysilyl)-1-propyl thiodecanoate;
3-(2-methyl-2,4-pentanedialkoxyethoxysilyl)-1-propyl thiododecanoate;
3-(2-methyl-2,4-pentanedialkoxyethoxysilyl)-1-propyl thiotetradecanoate;
3-(2-methyl-2,4-pentanedialkoxyethoxysilyl)-1-propyl thio-2-ethylhexanoate;
3-(2-methyl-2,4-pentanedialkoxyethoxysilyl)-1-propyl thio-2-methylheptanoate;
3-(2-methyl-2,4-pentanedialkoxyethoxysilyl)-1-propyl thiooctanoate;
3-(2-methyl-2,4-pentanedialkoxyethoxysilyl)-1-propyl thiodecanoate;
3-(2-methyl-2,4-pentanedialkoxymethylsilyl)-1-propyl thioacetate;
2-methyl-2,4-pentanedialkoxyisopropylsilylmethyl thioacetate;
6-(2-methyl-2,4-pentanedialkoxyethylsilyl)-1-hexyl thioacetate;
1-(2-methyl-2,4-pentanedialkoxymethylsilyl)-5-hexyl thioacetate;
8-(2-methyl-2,4-pentanedialkoxymethylsilyl)-1-octyl thioacetate;
10-(2-methyl-2,4-pentanedialkoxymethylsilyl)-1-decyl thioacetate;
3-(2-methyl-2,4-pentanedialkoxymethylsilyl)-1-propyl thiooctanoate;
3-(2-methyl-2,4-pentanedialkoxymethylsilyl)-1-propyl thiodecanoate;
3-(2-methyl-2,4-pentanedialkoxymethylsilyl)-1-propyl thiododecanoate;
3-(2-methyl-2,4-pentanedialkoxymethylsilyl)-1-propyl thio-2-ethylhexanoate;
3-(2-methyl-2,4-pentanedialkoxymethylsilyl)-1-propyl thio-2-methylheptanoate;
3-(1,3-butanedialkoxybutylsilyl)-1-propyl thioacetate;
3-(1,3-butanedialkoxyisopropylsilyl)-4-butyl thioacetate;
6-(1,3-butanedialkoxymethylsilyl)-1-hexyl thioacetate;
8-(1,3-butanedialkoxymethylsilyl)-1-octyl thioacetate;
10-(1,3-butanedialkoxymethylsilyl)-1-decyl thioacetate;
3-(1,3-butanedialkoxymethylsilyl)-1-propyl thiooctanoate;
3-(1,3-butanedialkoxymethylsilyl)-1-propyl thiodecanoate;
3-(1,3-butanedialkoxypropylsilyl)-1-propyl thiododecanoate;
3-(2,2-dimethyl-1,3-propanedialkoxymethylsilyl)-1-propyl thiodecanoate;
3-(2,2-dimethyl-1,3-propanedialkoxymethylsilyl)-1-propyl thiooctanoate;
3-(2-methyl-1,3-propanedialkoxymethylsilyl)-1-propyl thiooctanoate;
3-(2-methyl-1,3-propane dialkoxymethylsilyl)-1-propyl thiodecanoate;
3-(2-methyl-1,3-propane dialkoxymethylsilyl)-1-propyl thiododecanoate;
3-(2-methyl-1,3-propane dialkoxymethylsilyl)-1-propyl thiotetradecanoate;
3-(2-methyl-1,3-propane dialkoxymethylsilyl)-1-propyl thio-2-ethylhexanoate;
3-(2-methyl-1,3-propane dialkoxymethylsilyl)-1-propyl thio-2-methylheptanoate; and
neopentylglycoxypropylsilylmethyl thioacetate.