Silated core polysulfides, their preparation and use in filled elastomer compositions
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
B60C-001/00
C08K-005/24
C08K-003/34
출원번호
UP-0648287
(2006-12-28)
등록번호
US-7696269
(2010-05-20)
발명자
/ 주소
Cruse, Richard W.
York, W. Michael
Pohl, Eric R.
Joshi, Prashant
출원인 / 주소
Momentive Performance Materials Inc.
대리인 / 주소
Vicari, Dominick G.
인용정보
피인용 횟수 :
18인용 특허 :
106
초록▼
This invention relates to novel sulfur-containing silane coupling agents, and organic polymers containing carbon-carbon double bonds. These novel silanes can be carried on organic and inorganic fillers. The invention also relates to articles of manufacture, particularly tires, made from the elastome
This invention relates to novel sulfur-containing silane coupling agents, and organic polymers containing carbon-carbon double bonds. These novel silanes can be carried on organic and inorganic fillers. The invention also relates to articles of manufacture, particularly tires, made from the elastomer compositions described herein.
대표청구항▼
The invention claimed is: 1. A silated core polysulfide of the general formula [Y1R1Sx—]m[G1(R2SiX1X2X3)a]n[G2]o[R3Y2]p wherein: each occurrence of G1 is independently selected from a polyvalent hydrocarbon-containing species having from 3 to about 30 carbon atoms containing a polysulfi
The invention claimed is: 1. A silated core polysulfide of the general formula [Y1R1Sx—]m[G1(R2SiX1X2X3)a]n[G2]o[R3Y2]p wherein: each occurrence of G1 is independently selected from a polyvalent hydrocarbon-containing species having from 3 to about 30 carbon atoms containing a polysulfide group represented by the general formula: [(CH2)b—]cR4[—(CH2)dSx—]e; each occurrence of G2 is independently selected from a polyvalent hydrocarbon-containing species of 3 to about 30 carbon atoms containing a polysulfide group represented by the general formula: [(CH2)b—]cR5[—(CH2)dSx—]e; each occurrence of R1 and R3 is independently selected from a divalent hydrocarbon fragment having from 1 to about 20 carbon atoms; each occurrence of Y1 and Y2 is independently selected from the group consisting of silyl (—SiX1X2X3), hydrogen, carboxylic acid, ester (—C(═O)OR6) wherein R6 is a monovalent hydrocarbon group having from 1 to 20 carbon atoms; each occurrence of R2 is a chemical bond or a straight chain hydrocarbon represented by —(CH2)f—; each occurrence of X1 is independently selected from the group consisting of —Cl, —Br, —OH, OR6, and R6C(═O)O—, wherein R6 is a monovalent hydrocarbon group having from 1 to 20 carbon atoms; each occurrence of X2 and X3 is independently selected from the group consisting of hydrogen, R6, wherein R6 is a monovalent hydrocarbon group having from 1 to 20 carbon atoms, X1, wherein X1 is independently selected from the group consisting of —Cl, —Br, —OH, —OR6, and R6C(═O)O—, wherein R6 is a monovalent hydrocarbon group having from 1 to 20 carbon atoms, and —OSi containing groups that result from the condensation of silanols; each occurrence of the subscripts, a, b, c, d, e, f, m, n, o, p, and x, is independently given wherein a, c and e are 1 to about 3; b is 1 to about 5; d is 1 to about 5; f is 1 to about 5; m and p are 1 to about 100; n is 1 to about 15; o is 0 to about 10; and x is 1 to about 10; and, each occurrence of R4 and R5 is independently selected from a polyvalent heterocarbon fragment having from 1 to 27 carbon atoms. 2. The silated core polysulfide of claim 1 wherein the heteroatom of R4 and R5 is selected from the group consisting of sulfur, oxygen, nitrogen, and mixtures thereof. 3. The silated core polysulfide of claim 1 wherein the value of x is from 2 to 4. 4. A silated core polysulfide of the general formula [Y1R1Sx—]m[G1(R2SiX1X2X3)a]n[G2]o[R3Y2]p wherein: each occurrence of G1 is independently selected from a polyvalent hydrocarbon-containing species having from 1 to about 30 carbon atoms containing a polysulfide group represented by the general formula: [(CH2)b—]cR4[—(CH2)dSx—]e; each occurrence of G2 is independently selected from a polyvalent hydrocarbon-containing species of 1 to about 30 carbon atoms containing a polysulfide group represented by the general formula: [(CH2)b—]cR5[—(CH2)dSx—]e; each occurrence of R1 and R3 is independently selected from a divalent hydrocarbon fragment having from 1 to about 20 carbon atoms; each occurrence of Y1 and Y2 is independently selected from the group consisting of silyl (—SiX1X2X3), hydrogen, carboxylic acid, ester (—C(═O)OR6) wherein R6 is a monovalent hydrocarbon group having from 1 to 20 carbon atoms; each occurrence of R2 is a chemical bond or a straight chain hydrocarbon represented by —(CH2)f—; each occurrence of R4 is independently selected from a polyvalent hydrocarbon fragment of 1 to about 28 carbon atoms said fragment possessing a cyclic structure selected from the group consisting of bicyclic, tricyclic, higher cyclic structures, and cyclic structures substituted with alkyl, alkenyl and/or alkynyl groups; each occurrence of R5 is independently selected from a polyvalent hydrocarbon fragment of 1 to about 28 carbon atoms said fragment possessing a cyclic structure selected from the group consisting of bicyclic, tricyclic, higher cyclic structures, and cyclic structures substituted with alkyl, alkenyl and/or alkynyl groups; each occurrence of X1 is independently selected from the group consisting of —Cl, —Br, —OH, —OR6, and R6C(═O)O—, wherein R6 is a monovalent hydrocarbon group having from 1 to 20 carbon atoms and possesses a cyclic structure selected from the group consisting of bicyclic, tricyclic, higher cyclic structures, and cyclic structures substituted with alkyl, alkenyl and/or alkynyl groups; each occurrence of X2 and X3 is independently selected from the group consisting of hydrogen, R6, X1, wherein X1 is independently selected from the group consisting of —Cl, —Br, —OH, —OR6, and R6C(═O)O—, wherein R6 is a monovalent hydrocarbon group having from 1 to 20 carbon atoms and possesses a cyclic structure selected from the group consisting of bicyclic, tricyclic, higher cyclic structures, and cyclic structures substituted with alkyl, alkenyl and/or alkynyl groups, and —OSi containing groups that result from the condensation of silanols; and, each occurrence of the subscripts, a, b, c, d, e, f, m, n, o, p, and x, is independently given wherein a, c and e are 1 to about 3; b is 1 to about 5; d is 1 to about 5; f is 1 to about 5; m and p are 1 to about 100; n is 1 to about 15; o is 0 to about 10; and x is 1 to about 10. 5. The silated core polysulfide of claim 4 wherein the value of x is from 2 to 4. 6. A silated core polysulfide of the general formula [Y1R1Sx—]m[G1(R2SiX1X2X3)a]n[G2]o[R3Y2]p wherein: each occurrence of G1 is independently selected from a polyvalent hydrocarbon-containing species derived from nonconjugated diolefins, and having from 5 to about 30 carbon atoms containing a polysulfide group represented by the general formula: [(CH2)b—]cR4[—(CH2)dSx—]e; each occurrence of G2 is independently selected from a polyvalent hydrocarbon-containing species of 3 to about 30 carbon atoms containing a polysulfide group represented by the general formula: [(CH2)b—]cR5[—(CH2)dSx—]e; each occurrence of R1 and R3 is independently selected from a divalent hydrocarbon fragment having from 1 to about 20 carbon atoms; each occurrence of Y1 and Y2 is independently selected from the group consisting of silyl (—SiX1X2X3), hydrogen, carboxylic acid, ester (—C(═O)OR6) wherein R6 is a monovalent hydrocarbon group having from 1 to 20 carbon atoms; each occurrence of R2 is a chemical bond or a straight chain hydrocarbon represented by —(CH2)f—; each occurrence of R4 is independently selected from a polyvalent hydrocarbon fragment of 1 to about 28 carbon atoms; each occurrence of R5 is independently selected from a polyvalent hydrocarbon fragment of 1 to about 28 carbon atoms; each occurrence of X1 is independently selected from the group consisting of —Cl, —Br, —OH, —OR6, and R6C(═O)O—, wherein R6 is a monovalent hydrocarbon group having from 1 to 20 carbon atoms; each occurrence of X2 and X3 is independently selected from the group consisting of hydrogen, R6, wherein R6 is a monovalent hydrocarbon group having from 1 to 20 carbon atoms, X1, wherein X1 is independently selected from the group consisting of —Cl, —Br, —OH, —OR6, and R6C(═O)O—, wherein R6 is a monovalent hydrocarbon group having from 1 to 20 carbon atoms, and —OSi containing groups that result from the condensation of silanols; and, each occurrence of the subscripts, a, b, c, d, e, f, m, n, o, p, and x, is independently given wherein a, c and e are 1 to about 3; b is 1 to about 5; d is about 1 to 5; f is 1 to about 5; m and p are 1 to about 100; n is 1 to about 15; o is 0 to about 10; and x is 1 to about 10. 7. The silated core polysulfide of claim 6 wherein G1 is selected from the group consisting of —CH2(CH2)q+1CH(CH2—)— and —CH(CH3)(CH2)qCH(CH2—)2, wherein q is zero to 20. 8. The silated core polysulfide of claim 6 wherein G1 is —CH(CH2)(CH2)qCH(CH2—)—, in which q is from 1 to 20. 9. The silated core polysulfide of claim 6 wherein the value of x is from 2 to 4. 10. A silated core polysulfide selected from the group consisting of 2-triethoxysilyl-1,3-bis-(3-triethoxysilyl-1-propyltetrathia)propane, 4-(2-triethoxysilyl-1-ethyl)-1,2-bis-(13-triethoxysilyl-3,4,5,6-tetrathiamidecyl)cyclohexane; 4-(2-triethoxysilyl-1-ethyl)-1,2-bis-(13-triethoxysilyl-3,4,5,6-tetrathiamidecyl)cyclohexane; 4-(2-diethoxymethylsilyl-1-ethyl)-1,2-bis-(13-triethoxysilyl-3,4,5,6-tetrathiamidecyl)cyclohexane; 4-(2-triethoxysilyl-1-ethyl)-1,2-bis-(10-triethoxysilyl-3,4,5,6,7-pentathiadecyl)cyclohexane; 1-(2-triethoxysilyl-1-ethyl)-2,4-bis-(10-triethoxysilyl-3,4,5,6,7-pentathiadecyl)cyclohexane; 4-(2-triethoxysilyl-1-ethyl)-1,2-bis-(9-triethoxysilyl-3,4,5,6-tetrathianonyl)cyclohexane; 1-(2-triethoxysilyl-1-ethyl)-2,4-bis-(9-triethoxysilyl-3,4,5,6-tetrathianonyl)cyclohexane; 2-(2-triethoxysilyl-1-ethyl)-1,4-bis-(9-triethoxysilyl-3,4,5,6-tetrathianonyl)cyclohexane; 4-(2-triethoxysilyl-1-ethyl)-1,2-bis-(8-triethoxysilyl-3,4,5-trithiaoctyl)cyclohexane; 1-(2-triethoxysilyl-1-ethyl)-2,4-bis-(8-triethoxysilyl-3,4,5-trithiaoctyl)cyclohexane; 2-(2-triethoxysilyl-1-ethyl)-1,4-bis-(8-triethoxysilyl-3,4,5-trithiaoctyl)cyclohexane; 4-(2-triethoxysilyl-1-ethyl)-1,2-bis-(7-triethoxysilyl-3,4-dithiaheptyl)cyclohexane; 2-(2-triethoxysilyl-1-ethyl)-1,4-bis-(7-triethoxysilyl-3,4-dithiaheptyl)cyclohexane; 1-(2-triethoxysilyl-1-ethyl)-2,4-bis-(7-triethoxysilyl-3,4-dithiaheptyl)cyclohexane; 2-(2-triethoxysilyl-1-ethyl)-1-(7-triethoxysilyl-3,4-dithiaheptyl)-2-(8-triethoxysilyl-3,4,5-trithiaoctyl)cyclohexane; 4-(2-triethoxysilyl-1-ethyl)-1,2-bis-(9-triethoxysilyl-3,4,5,6-tetrathianonyl)benzene; bis-[2-[4-(2-triethoxysilyl-1-ethyl)-2-(9-triethoxysilyl-3,4,5,6-tetrathianonyl)cyclohexyl]ethyl]tetrasulfide; bis-[2-(4-(2-triethoxysilyl-1-ethyl)-2-(9-triethoxysilyl-3,4,5,6-tetrathianonyl)cyclohexyl]ethyl]trisulfide; bis-[2-[4-(2-triethoxysilyl-1-ethyl)-2-(9-triethoxysilyl-3,4,5,6-tetrathianonyl)cyclohexyl]ethyl]disulfide; bis-[2-[4-(2-triethoxysilyl-1-ethyl)-2-(7-triethoxysilyl-3,4-dithiaheptyl)cyclohexyl]ethyl]disulfide; bis-2-[4-(2-triethoxysilyl-1-ethyl)-2-(7-triethoxysilyl-3,4-dithiaheptyl)cyclohexyl]ethyl]trisulfide; bis-[2-[4-(2-triethoxysilyl-1-ethyl)-2-(7-triethoxysilyl-3,4-dithiaheptyl)cyclohexyl]ethyl tetrasulfide; bis-[2-[4-(2-triethoxysilyl-1-ethyl)-2-(9-triethoxysilyl-3,4,5,6-tetrathianonyl)phenyl]ethyl]tetrasulfide; bis-2-[4-(2-triethoxysilyl-1-ethyl)-3-bis-(9-triethoxysilyl-3,4,5,6-tetrathianonyl)cyclohexyl]ethyl]trisulfide; bis-[2-[4-(2-diethoxymethylsilyl-1-ethyl)-2-(7-triethoxysilyl-3,4-dithiaheptyl)cyclohexyl]ethyl disulfide, and mixtures thereof. 11. The silated core polysulfide of claim 10 wherein said silated core polysulfide is selected from the group consisting of 4-(2-triethoxysilyl-1-ethyl)-1,2-bis-(9-triethoxysilyl-3,4,5,6-tetrathianonyl)cyclohexane, 1-(2-triethoxysilyl-1-ethyl)-2,4-bis-(9-triethoxysilyl-3,4,5,6-tetrathianonyl)cyclohexane, 2-(2-triethoxysilyl-1-ethyl)-1,4-bis-(9-triethoxysilyl-3,4,5,6-tetrathianonyl)cyclohexane and mixtures thereof. 12. A silated core polysulfide of the general formula [Y1R1Sx—]m[G1(R2SiX1X2X3)a]n[G2]o[R3Y2]p wherein: each occurrence of G1 is independently selected from a polyvalent hydrocarbon-containing species having from 5 to about 30 carbon atoms containing a polysulfide group represented by the general formula: [(CH2)b—]cR4[—(CH2)dSx—]e; each occurrence of G2 is independently selected from a polyvalent hydrocarbon-containing species of 3 to about 30 carbon atoms containing a polysulfide group represented by the general formula: [(CH2)b—]cR5[—(CH2)dSx—]e; each occurrence of R1 and R3 is independently selected from a divalent hydrocarbon fragment having from 1 to about 5 carbon atoms; each occurrence of Y1 and Y2 is independently selected from the group consisting of silyl (—SiX1X2X3), hydrogen, carboxylic acid, ester (—C(═O)OR6) wherein R6 is a monovalent hydrocarbon group having from 1 to 20 carbon atoms; each occurrence of R2 is a chemical bond or a straight chain hydrocarbon represented by —(CH2)f—; each occurrence of R4 is independently selected from a polyvalent hydrocarbon fragment of 3 to about 10 carbon atoms; each occurrence of R5 is independently selected from a polyvalent hydrocarbon fragment of 1 to about 28 carbon atoms; each occurrence of X1 is independently selected from the group consisting of —Cl, —Br, —OH, —OR6, and R6C(═O)O—, wherein R6 is a monovalent hydrocarbon group having from 1 to 20 carbon atoms; each occurrence of X2 and X3 is independently selected from the group consisting of hydrogen, R6, wherein R6 is a monovalent hydrocarbon group having from 1 to 20 carbon atoms, X1, wherein X1 is independently selected from the group consisting of —Cl, —Br, —OH, —OR6, and R6C(═O)O—, wherein R6 is a monovalent hydrocarbon group having from 1 to 20 carbon atoms, and —OSi containing groups that result from the condensation of silanols; and; each occurrence of the subscripts, a, b, c, d, e, f, m, n, o, p, and x, is independently given wherein a, c and e are 1 to about 3; b is 1 to about 5; d is 1 to about 5; f is 1 to about 5; in and p are 1 to about 100; n is 1 to about 15; o is 0 to about 10; and x is 1 to about 10. 13. The silated core polysulfide of claim 12 wherein the value of x is from 2 to 4. 14. The silated core polysulfide of claim 12 wherein R1 and R3 are branched and/or straight chain alkyl, alkenyl or alkynyl groups in which one hydrogen atom is substituted with a Y1 or Y2 group. 15. The silated core polysulfide of claim 12 wherein Y1 and Y2 are silyl (—SiX1X2X3), hydrogen, carboxylic acid, or ester (—C(═O)OR6) wherein R6 is a monovalent hydrocarbon group having from 1 to 5 carbon atoms. 16. The silated core polysulfide of claim 12 wherein R2 is a straight chain hydrocarbon represented by —(CH2)f— where f is an integer from 1 to about 3. 17. The silated core polysulfide of claim 12 wherein R5 is a polyvalent hydrocarbon fragment of 3 to about 10 carbon atoms. 18. The silated core polysulfide of claim 12 wherein X1 is independently selected from the group consisting of hydrolysable —OH, and —OR6, wherein R6 is a monovalent hydrocarbon group having from 1 to 5 carbon atoms. 19. The silated core polysulfide of claim 12 wherein X2 and X3 are independently selected from the group consisting of R6, wherein R6 is a monovalent hydrocarbon group having from 1 to 5 carbon atoms, X1, wherein X1 is independently selected from the group consisting of hydrolysable —OH, —OR6, and —OSi containing groups that result from the condensation of silanols. 20. The silated core polysulfide of claim 12 wherein each occurrence of the subscripts, a, b, c, d, e, f, m, n, o, p, and x, is independently given by a is 1 to about 2; b and d are 1 to about 3; c and e are 1; f is 1 to about 3; m and p are 1, n is 1 to about 10; o is 0 to about 1; and x is 1 to about 4.
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