Cyclic diol-derived blocked mercaptofunctional silane compositions

Patent metadata

Field	Value
Publication number	US-9290520-B2
Application number	US-201314088825-A
Country	US
Kind code	B2
Filing date	Nov 25, 2013
Priority date	Aug 20, 2004
Publication date	Mar 22, 2016
Grant date	Mar 22, 2016

Abstract

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.

First claim

What is claimed is:

1. A process for the preparation of a 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 polyvalent group containing from 1 to 30 carbon atoms derived from an 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 group consisting of (—O—) 0.5 and [—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, t, and 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; j 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 and wherein that 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 ,
the process comprising reacting an aqueous solution of a salt of at least one thioacid with at least one cyclic and bridging dialkoxy haloalkyl silane and, optionally, at least one haloalkyl silane to provide cyclic and bridging dialkoxy silane composition.

2. The process of claim 1 , wherein the cyclic and bridging dialkoxy haloalkyl silane is:
[L r -G-(SiX u Z b v Z w ) s ] n ,

and the structure for the thiocarboxylate salt is selected from the group consisting of the formula:
[(ROC(═O)) p -(G) j ]-Y 1 —SM and

(Z c w Z b v X u Si) q -G-Y 1 —SM

wherein
each occurrence of M is independently selected from alkali metal; ammonium; and mono-, di-, or tri- substituted ammonium;
each occurrence of Y 1 is carbonyl;
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, monovalent alkyl, alkenyl, aryl or aralkyl group containing from 1 to 30 carbon atoms, and polyvalent group containing from 1 to 30 carbon atoms derived from 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 group consisting of (—O—) 0.5 and [—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 L is independently chloro or bromo, and
each occurrence of the subscripts, f, j, n, p, q, u, v, w, r, t, and s is independently given by f is 1 to 15; j is 0 to 1, with the proviso that when j is 0 p is 1; 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; p is 0 to 5; q is 0 to 6; u is 0 to 3; v is 0 to 3; w is 0 to 1 with the proviso that u+v+2w is 3; r is 1 to 3; t is 0 to 50, and s is 1 to 3 and wherein the structure, [L r -G-(SiX u Z b v Z w ) s ] n , comprises at least two hydrolysable bridging dialkoxy groups, Z b , or at least one hydrolysable cyclic dialkoxy group, Z c .

3. The process of claim 1 , wherein the reaction temperature is about 40 to about 85° C. and the pressure is ambient.

4. The process of claim 1 , wherein the reaction is carried out in the presence of at least one phase transfer catalyst of the formula:
(R 6 R 7 R 8 R 9 N + ) m A −m

wherein each occurrence of R 6 , R 7 , R 8 and R 9 is independently R, where R is 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; N is nitrogen; A −m is a monovalent or polyvalent anion selected from the group consisting of fluoride, chloride, bromide, iodide, sulfate, bisulfate, carbonate, bicarbonate, hydroxide, phosphate, carbox late and h drosulfide, where the minus sign denotes that the species is an anion, and m denotes the number of negative charges on the anion; and the subscript m is a positive integer of from 1 to 6.

5. The process of claim 4 , wherein the phase transfer catalyst is selected from the group consisting of tetramethylammonium chloride, tetramethylammonium bromide, tetramethylammonium iodide, tetramethylammonium hydroxide, tetraethylammonium chloride, tetraethylammonium bromide, tetraethylammonium iodide, tetraethylammonium hydroxide, tetrabutylammonium chloride, tetrabutylammonium bromide, tetrabutylammonium iodide, tetrabutylammonium hydroxide, methyltributylammonium chloride, methyltributylammonium bromide, methyltributylammonium iodide, methyltributylammonium hydroxide, tetraoctyl ammonium chloride, tetraoctylammonium bromide, tetraoctylammonium iodide, tetraoctylammonium hydroxide, methyltrioctylammonium chloride, methyltrioctylammonium bromide, methyltrioctylammonium iodide, methyltrioctylammonium hydroxide, benzyltrimethylammonium chloride, benzyltrimethylammonium bromide, benzyltriethylammonium chloride, benzyltributylammonium chloride, dibenzyldimethylammonium chloride, dibenzyldimethylammonium bromide, dibenzyldiethylammonium chloride and dibenzyldibutylammonium chloride.

6. A process for the preparation of a 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 gr

Assignees

• Cruse Richard W
• Gonzalez Leda N
• Himmeldirk Rodica
• Divens Larry Allen
• Jackson Melinda
• Pohl Eric Raymond
• Chaves Antonio
• Momentive Performance Mat Inc

Inventors

• Cruse Richard W
• Gonzalez Leda N
• Himmeldirk Rodica
• Divens Larry Allen
• Jackson Melinda
• Pohl Eric Raymond
• Chaves Antonio

Classifications

• C08K5/54 Primary

  Silicon-containing compounds {(C08K5/0091 takes precedence)} · CPC title

• C08K5/549

  containing silicon in a ring · CPC title

• C07F7/081 Primary

  comprising at least one atom selected from the elements N, O, halogen, S, Se or Te · CPC title

• C08L9/06

  Copolymers with styrene · CPC title

• C07F7/1804

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title