Granted Patent B2

US 12,570,833 · App. 18/064,169 · Granted Mar 10, 2026

Inventors: Matthew J. Pinnow (Tarrytown, NY); Adeyemi A. Adepetun (Charlotte, NC); Richard W. Cruse (Tarrytown, NY); Lesley Hwang (Chappaqua, NY); Nancy Winchester (Charlotte, NC); Linda Vecere (Tarrytown, NY); Yanjun Zhu (Tarrytown, NY)

Assignee: MOMENTIVE PERFORMANCE MATERIALS INC.

C08K5/544B60C1/0016C08F136/06C08F136/08C08K3/36C08K5/548C08K2201/006

Abstract

Claims (83)

1 . A composition comprising at least one silane functional amine, wherein the at least one silane functional amine is a compound of formula (I): (R 1 ) a -G-(NR 2 ) b ; and further wherein:

G is an unsaturated cyclic moiety;

each R 1 is independently selected from the group consisting of an alkoxyl group having from 1 to 20 carbon atoms, an alkyl group having from 1 to 20 carbon atoms, an alkenyl group having from 2 to 20 carbon atoms, a cycloalkyl group having from 3 to 10 carbon atoms, an aryl group having from 6 to 12 carbon atoms, and an aralkyl group having from 7 to 14 carbon atoms;

each R is independently selected from the group consisting of hydrogen and -L-SiX 1 X 2 X 3 ; with the proviso that at least one R is hydrogen and at least two R is -L-SiX 1 X 2 X 3 ;

each L is independently selected from the group consisting of an alkylene group having from 1 to 20 carbon atoms and optionally at least one heteroatom, an alkenylene group having from 2 to 20 carbon atoms, a cycloalkylene group having from 3 to 10 carbon atoms, an arylene group having from 6 to 12 carbon atoms, and an aralkylene group having from 7 to 14 carbon atoms;

each X 1 is independently selected from the group consisting of hydroxyl, —OR 2 and —OC(═O)R 2 ;

each X 2 and each X 3 are independently selected from the group consisting of hydroxyl, —OR 2 , —OC(═O)R 2 and R 2 ;

each R 2 is independently selected from the group consisting of an alkyl group having from 1 to 20 carbon atoms, an alkenyl group having from 2 to 20 carbon atoms, a cycloalkyl group having from 3 to 10 carbon atoms, an aryl group having from 6 to 12 carbon atoms, and an aralkyl group having from 7 to 14 carbon atoms;

a is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; and

b is 2.

2 . The composition of claim 1 , wherein G is selected from the group consisting of a benzene ring and a pyridine ring.

3 . The composition of claim 1 , wherein the compound of formula (I) is selected from the group consisting of

and combinations thereof.

4 . The composition of claim 1 , wherein the compound of formula (I) is selected from the group consisting of

and combinations thereof.

5 . A method for preparing the composition comprising at least one silane functional amine of claim 1 , comprising reacting a compound of formula (II): (R 1 ) a -G-(NH 2 ) b , with one or more compounds of formula (III): M-L-SiX 1 X 2 X 3 ; wherein the total molar ratio of compounds of formula (III) to the compound of formula (II) is from 3.0:1 to 0.1:1; and further wherein:

G is an unsaturated cyclic moiety;

each R 1 is independently selected from the group consisting of an alkoxyl group having from 1 to 20 carbon atoms, an alkyl group having from 1 to 20 carbon atoms, an alkenyl group having from 2 to 20 carbon atoms, a cycloalkyl group having from 3 to 10 carbon atoms, an aryl group having from 6 to 12 carbon atoms, and an aralkyl group having from 7 to 14 carbon atoms;

each L is independently selected from the group consisting of an alkylene group having from 1 to 20 carbon atoms and optionally at least one heteroatom, an alkenylene group having from 2 to 20 carbon atoms, a cycloalkylene group having from 3 to 10 carbon atoms, an arylene group having from 6 to 12 carbon atoms, and an aralkylene group having from 7 to 14 carbon atoms;

each X 1 is independently selected from the group consisting of hydroxyl, —OR 2 and —OC(═O)R 2 ;

each X 2 and each X 3 are independently selected from the group consisting of hydroxyl, —OR 2 , —OC(═O)R 2 and R 2 ;

each R 2 is independently selected from the group consisting of an alkyl group having from 1 to 20 carbon atoms, an alkenyl group having from 2 to 20 carbon atoms, a cycloalkyl group having from 3 to 10 carbon atoms, an aryl group having from 6 to 12 carbon atoms, and an aralkyl group having from 7 to 14 carbon atoms;

each M is independently halogen;

a is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; and

b is 2.

6 . The method of claim 5 , wherein G is selected from the group consisting of a benzene ring and a pyridine ring.

7 . The method of claim 5 , wherein the at least one silane functional amine is selected from the group consisting of

and combinations thereof.

8 . The method of claim 5 , wherein the total molar ratio of compounds of formula (III) to the compound of formula (II) is from 1.5:1 to 0.7:1.

9 . The method of claim 5 , wherein each M is independently chloro, bromo or iodo.

10 . The method of claim 5 , wherein the reacting occurs in the presence of a base.

11 . The method of claim 10 , wherein the base is an alkali metal alkoxide.

12 . A rubber composition comprising:

(a) a composition comprising at least one silane functional amine, wherein the at least one silane functional amine is a compound of formula (I): (R 1 ) a -G-(NR 2 ) b ; and further wherein:

G is a saturated or an unsaturated cyclic moiety;

each R 1 is independently selected from the group consisting of an alkoxyl group having from 1 to 20 carbon atoms, an alkyl group having from 1 to 20 carbon atoms, an alkenyl group having from 2 to 20 carbon atoms, a cycloalkyl group having from 3 to 10 carbon atoms, an aryl group having from 6 to 12 carbon atoms, and an aralkyl group having from 7 to 14 carbon atoms;

each R is independently selected from the group consisting of hydrogen and -L-SiX 1 X 2 X 3 , with the proviso that at least one R is hydrogen and at least one R is -L-SiX 1 X 2 X 3 ;

each L is independently selected from the group consisting of an alkylene group having from 1 to 20 carbon atoms and optionally at least one heteroatom, an alkenylene group having from 2 to 20 carbon atoms, a cycloalkylene group having from 3 to 10 carbon atoms, an arylene group having from 6 to 12 carbon atoms, and an aralkylene group having from 7 to 14 carbon atoms;

each X 1 is independently selected from the group consisting of hydroxyl, —OR 2 and —OC(═O)R 2 ;

each X 2 and each X 3 are independently selected from the group consisting of hydroxyl, —OR 2 , —OC(═O)R 2 and R 2 ;

each R 2 is independently selected from the group consisting of an alkyl group having from 1 to 20 carbon atoms, an alkenyl group having from 2 to 20 carbon atoms, a cycloalkyl group having from 3 to 10 carbon atoms, an aryl group having from 6 to 12 carbon atoms, and an aralkyl group having from 7 to 14 carbon atoms;

a is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; and

b is 1 or 2;

(b) at least one diene-based polymer;

(c) silica;

(d) at least one process aid; and

(e) a vulcanizing package comprising at least one vulcanizing agent comprising sulfur and at least one accelerator.

13 . The rubber composition of claim 12 , wherein G of the at least one silane functional amine of (a) is selected from the group consisting of a benzene ring, a cyclohexane ring, and a pyridine ring.

14 . The rubber composition of claim 12 , wherein the compound of formula (I) of the at least one silane functional amine of (a) is selected from the group consisting of

and combinations thereof.

15 . The rubber composition of claim 12 , wherein the at least one diene-based polymer is a diene-based polymer containing at least one functional group, a diene-based polymer containing no functional group, or combinations thereof.

16 . The rubber composition of claim 12 , wherein the at least one diene-based polymer is natural rubber, polyisoprene, a polybutadiene, styrene-butadiene copolymer (SBR), or combinations thereof.

17 . The rubber composition of claim 16 , wherein the at least one diene-based polymer is natural rubber, cis 1,4-polyisoprene, cis 1,4-polybutadiene, or combinations thereof.

18 . A rubber composition comprising:

(i) about 100 parts of rubber, where the weight of the rubber is the sum of the weights of each diene-based polymer containing at least one functional group used in the composition and the weights of each diene-based polymer containing no functional group used in the composition;

(ii) about 1 to about 20 parts by weight per 100 parts rubber (i) of the composition comprising at least one silane functional amine, wherein the at least one silane functional amine is a compound of formula (I): (R 1 ) a -G-(NR 2 ) b ; and further wherein:

G is a saturated or an unsaturated cyclic moiety;

each R 1 is independently selected from the group consisting of an alkoxyl group having from 1 to 20 carbon atoms, an alkyl group having from 1 to 20 carbon atoms, an alkenyl group having from 2 to 20 carbon atoms, a cycloalkyl group having from 3 to 10 carbon atoms, an aryl group having from 6 to 12 carbon atoms, and an aralkyl group having from 7 to 14 carbon atoms;

each R is independently selected from the group consisting of hydrogen and -L-SiX 1 X 2 X 3 , with the proviso that at least one R is hydrogen and at least one R is -L-SiX 1 X 2 X 3 ;

each L is independently selected from the group consisting of an alkylene group having from 1 to 20 carbon atoms and optionally at least one heteroatom, an alkenylene group having from 2 to 20 carbon atoms, a cycloalkylene group having from 3 to 10 carbon atoms, an arylene group having from 6 to 12 carbon atoms, and an aralkylene group having from 7 to 14 carbon atoms;

each X 1 is independently selected from the group consisting of hydroxyl, —OR 2 and —OC(═O)R 2 ;

each X 2 and each X 3 are independently selected from the group consisting of hydroxyl, —OR 2 , —OC(═O)R 2 and R 2 ;

each R 2 is independently selected from the group consisting of an alkyl group having from 1 to 20 carbon atoms, an alkenyl group having from 2 to 20 carbon atoms, a cycloalkyl group having from 3 to 10 carbon atoms, an aryl group having from 6 to 12 carbon atoms, and an aralkyl group having from 7 to 14 carbon atoms;

a is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; and

b is 1 or 2;

(iii) about 5 to about 140 parts by weight per 100 parts rubber (i) of silica;

(iv) about 0.1 to about 10 parts by weight per 100 parts rubber (i) of at least one process aid; and

(v) about 0.1 to about 20 parts by weight per 100 parts rubber (i) of a vulcanization package comprising at least one vulcanizing agent comprising sulfur and at least one accelerator.

19 . The rubber composition of claim 18 , wherein G of the at least one silane functional amine of (ii) is selected from the group consisting of a benzene ring, a cyclohexane ring, and a pyridine ring.

20 . The rubber composition of claim 18 , wherein the compound of formula (I) of the at least one silane functional amine of (ii) is selected from the group consisting of

and combinations thereof.

21 . A process of preparing a rubber composition comprising adding a composition comprising at least one silane functional amine, wherein the at least one silane functional amine is a compound of formula (I): (R 1 ) a -G-(NR 2 ) b ; and further wherein:

G is a saturated or an unsaturated cyclic moiety;

each R 1 is independently selected from the group consisting of an alkoxyl group having from 1 to 20 carbon atoms, an alkyl group having from 1 to 20 carbon atoms, an alkenyl group having from 2 to 20 carbon atoms, a cycloalkyl group having from 3 to 10 carbon atoms, an aryl group having from 6 to 12 carbon atoms, and an aralkyl group having from 7 to 14 carbon atoms;

each R is independently selected from the group consisting of hydrogen and -L-SiX 1 X 2 X 3 ; with the proviso that at least one R is hydrogen and at least one R is -L-SiX 1 X 2 X 3 ;

each L is independently selected from the group consisting of an alkylene group having from 1 to 20 carbon atoms and optionally at least one heteroatom, an alkenylene group having from 2 to 20 carbon atoms, a cycloalkylene group having from 3 to 10 carbon atoms, an arylene group having from 6 to 12 carbon atoms, and an aralkylene group having from 7 to 14 carbon atoms;

each X 1 is independently selected from the group consisting of hydroxyl, —OR 2 and —OC(═O)R 2 ;

each X 2 and each X 3 are independently selected from the group consisting of hydroxyl, —OR 2 , —OC(═O)R 2 and R 2 ;

each R 2 is independently selected from the group consisting of an alkyl group having from 1 to 20 carbon atoms, an alkenyl group having from 2 to 20 carbon atoms, a cycloalkyl group having from 3 to 10 carbon atoms, an aryl group having from 6 to 12 carbon atoms, and an aralkyl group having from 7 to 14 carbon atoms;

a is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; and

b is 1 or 2;

and silica to at least one diene-based polymer.

22 . An article of manufacture comprising the rubber composition of claim 18 , wherein the article of manufacture is a tire or engine mount.

Assignments (5)

Continuity (2)

References Cited (16)