Granted Patent B2

US 7,531,680 · App. 11/443,937 · Granted May 12, 2009

Abstract

Claims (32)

1. A method for coupling an elastomer and a filler comprising employing at least one silane coupling agent wherein said silane comprises at least one hydrolysable group that, upon compounding said silane with said elastomer and filler, is released to yield a compound that improves downstream processability of the compounded composition or the properties of the final rubber product or both, wherein said silane coupling agent is selected from the group consisting of silanes whose individual structures are represented by at least one of the following general formulae:

[J-S-G 1 -(SiX 2 X 3 )][—Y 2 —(X 2 Si-G 1 -S-J)] m —X 1 ;  Formula 1:

[X 1 X 2 X 3 Si-G 2 -S x -G 3 -Si(X 2 X 3 )][—Y 2 —(X 2 Si)-G 2 -S x -G 3 -(SiX 1 X 2 X 3 )] m —X 1 ;  Formula 2:

[X 1 X 2 X 3 Si-G 2 -S x -G 3 -Si(X 2 X 3 )][—Y 2 —(X 2 X 3 Si)-G 2 -S x -G 3 -(SiX 2 X 3 )] n —X 1 ; and  Formula 3:

[(—Y 2 —) y/2 (X 2 3-h Si)-G-S-J] m [(—Y 2 —) j/2 (X 2 3-j Si)-G-S x -G 3 -(SiX 2 3-k )(—Y 2 —) k/2 ] n   Formula 4:

wherein, in formulae 1 through 4:

each occurrence of the subscript, h, is independently an integer from 1 to 3;

each separate occurrence of the subscripts, j and k, is independently an integer from 0 to 3, with the proviso that j+k>0;

each occurrence of the subscript, m, is independently an integer from 1 to 1000;

each occurrence of the subscript, n, is independently an integer from 1 to 1000;

each occurrence of the subscript, x, is independently an integer from 2 to 20;

each occurrence of X 1 is independently selected from the group of hydrolysable moieties consisting of —Y 1 , —OH, —OR 1 , and R 1 C(═O)O—, wherein each occurrence of R 1 is independently any hydrocarbon fragment obtained by removal of one hydrogen atom from a hydrocarbon having from 1 to 20 carbon atoms, and R 1 includes aryl groups and any branched or straight chain alkyl, alkenyl, arenyl, or aralkyl groups;

each occurrence of X 2 and X 3 is independently selected from the group consisting of hydrogen, R 1 , and X 1 ;

each occurrence of G 1 , G 2 , and G 3 is independently selected from the group consisting of hydrocarbon fragments obtained by removal of one hydrogen atom of any of the groups listed above for R 1 ;

each occurrence of J is independently selected from the group consisting of R 1 C(═O)—, R 1 C(═S)—, R 1 2 P(═O)—, R 1 2 P(═S)—, R 1 S(═O)—, and R 1 S(═O) 2 —, wherein each separate occurrence of R 1 is as defined above;

each occurrence of Y 1 is independently —O-G-(O-G-) p OR or —O-G-(O-G-) p OH and each occurrence of Y 2 is independently —O-G-(O-G-) q O—,

each occurrence of the subscript, p, is independently an integer from 1 to 100;

each occurrence of the subscript, q, is independently an integer from 1 to 100;

each occurrence of G is independently selected from the group consisting of hydrocarbon fragments obtained by removal of one hydrogen atom of any of the groups listed above for R 1 ; and

each occurrence of R is independently selected from the group consisting of the members listed above for R 1 .

2. A method for preparing a silane coupling agent for coupling an elastomer and a filler wherein said silane comprises at least one hydrolysable group that, upon compounding said silane with said elastomer and filler, is released to yield a compound that improves downstream processability of the compounded composition or the properties of the final rubber product or both, wherein said method comprises transesterifying JSG 1 -(SiX 1 X 2 X 3 ) or X 1 X 2 X 3 Si-G 2 -S x -G 3 -SiX 1 X 2 X 3 or mixtures thereof with an etheralcohol of the general formula (8) given below

HO-G-(O-G-) q OH,  Formula 8:

wherein each occurrence of G is independently selected from the group consisting of hydrocarbon fragments obtained by removal of one hydrogen atom from any of the groups including aryl groups and any branched or straight chain alkyl, alkenyl, arenyl, or aralkyl groups, and

each occurrence of the subscript, q, is independently an integer from 1 to 100: and, wherein:

each occurrence of the subscript, x, is independently an integer from 2 to 20;

each occurrence of X 1 is independently selected from the group of hydrolysable moieties consisting of —Y 1 , —OH, —OR 1 , and R 1 C(═O)O—, wherein each occurrence of R 1 is independently any hydrocarbon fragment obtained by removal of one hydrogen atom from a hydrocarbon having from 1 to 20 carbon atoms, R 1 includes aryl groups and any branched or straight chain alkyl, alkenyl, arenyl, or aralkyl groups, and each occurrence of —Y 1 is independently —O-G-(O-G-) p OR or —O-G-(O-G-) p OH, where each occurrence of R is independently selected from the group consisting of the members listed above for R 1 , and each occurrence of the subscript, p, is independently an integer from 1 to 100;

each occurrence of X 2 and X 3 is independently selected from the group consisting of hydrogen, R 1 , and X 1 ;

each occurrence of G 1 , G 2 , and G 3 is independently selected from the group consisting of hydrocarbon fragments obtained by removal of one hydrogen atom of any of the groups listed above for R 1 ;

each occurrence of J is independently selected from the group consisting of R 1 C(═O)—, R 1 C(═S)—, R 1 2 P(═O)—, R 1 2 P(═S)—, R 1 S(═O)—, and R 1 S(═O) 2 —, wherein each separate occurrence of R 1 is as defined above.

3. The method of claim 2 wherein the etheralcohol is diethylene glycol.

4. The method of claim 2 further comprising carrying out the transesterification reaction in the presence of a catalyst.

5. The method of claim 4 wherein the catalyst is para-toluenesulfonic acid.

Assignments (23)