Blocked mercaptosilane coupling agents, process for making the uses in rubber
View Patent ↗The invention relates to sulfur silane coupling agents containing multiple blocked mercapto groups which are in a state of reduced activity until activated. The coupling agents are advantageously used in rubber formulations, for example, for fabricating tires with low rolling resistance.
1. A compound having the structure (2-triethoxysilylethyl)bis-(3-thia-4-oxopentyl)cyclohexane.
2. A method for making the compound of claim 1 comprising reacting a thioacetic acid with (2-triethoxysilylethyl)divinylcyclohexane.
3. The method of claim 1 , wherein the reaction is catalyzed by UV radiation.
4. The method of claim 2 , wherein the reaction is conducted in the presence of a free radical initiator.
5. The method of claim 4 , wherein the free radical initiator is selected from the group consisting of air, peracid, ester of peracid, peroxide, hydroperoxide, peroxy-acetal, peroxy-ketal, azobisisobutyronitrile, 1,1-azobis(cyclohexanecarbonitrile) and azo-tert-butane.
6. The method of claim 4 , wherein the reaction is conducted at a temperature below 90° C.
7. A rubber composition including a compound of claim 1 .
8. A rubber composition comprising:
(a) a compound of claim 1 ;
(b) an organic polymer;
(c) a filler; and optionally,
(d) other additives and curatives.
9. The rubber composition of claim 8 wherein the organic polymer (b) is selected from the group consisting of solution styrene-butadiene rubber, emulsion styrene-butadiene rubber, natural rubber, polybutadiene rubber, ethylene-propylene copolymer, ethylene-propylene-diene monomer (EPDM), acrylonitrile-butadiene rubber, cis-1,4-polyisoprene rubber, 3,4-polyisoprene rubber, cis-1,4-polybutadiene rubber, medium vinyl polybutadiene rubber, high vinyl polybutadiene rubber, and mixtures thereof.
10. The rubber composition of claim 8 wherein the filler (c) is selected from the group consisting of pyrogenic silica, precipitated silica, titanium dioxide, aluminosilicate, alumina, clay, talc and carbon black.
11. A process for preparing a cured rubber composition comprising:
(A) thermomechanically mixing, in at least one preparatory mixing step, to a temperature of from 140° to 200° C. and for a total mixing time of 2 to 20 minutes,
(i) 100 parts by weight of at least one sulfur vulcanizable rubber selected from conjugated diene homopolymer, conjugated diene copolymer, and copolymer of at least one conjugated diene and aromatic vinyl compound,
(ii) 5 to 100 parts per hundred rubber of at least one particulate filler,
(iii) 0.05 to 20 parts by weight filler of a compound having the structure of claim 1 ;
(B) subsequently blending therewith, in a final thermomechanical mixing step at a temperature to 50° to 130° C., the rubber of step (A), at least one deblocking agent in an amount of from 0.05 to 20 parts by weight of the filler and a curing agent in an amount of from 0 to 5 parts per hundred parts rubber; and
(C) curing said mixture.
12. The process of claim 11 , wherein the particulate filler is selected from the group consisting of pyrogenic silica, precipitated silica, titanium dioxide, aluminosilicate, alumina, clay, talc and carbon black.
13. The process of claim 11 wherein the sulfur vulcanizable rubber is selected from the group consisting of solution styrene-butadiene rubber, emulsion styrene-butadiene rubber, natural rubber, polybutadiene rubber, ethylene-propylene copolymer, ethylene-propylene-diene monomer (EPDM), acrylonitrile-butadiene rubber, cis-1,4-polyisoprene rubber, 3,4-polyisoprene rubber, cis-1,4-polybutadiene rubber, medium vinyl polybutadiene rubber and high vinyl polybutadiene rubber.
14. A free flowing filler composition comprising the compound of claim 1 and at least one particulate filler.
15. The free flowing filler composition of claim 14 wherein the particulate filler is selected from the group consisting of pyrogenic silica, precipitated silica, titanium dioxide, aluminosilicate, alumina, clay, talc and carbon black.