Silated cyclic core polysulfides, their preparation and use in filled elastomer compositions
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
B60C-001/00
C08K-005/24
C01B-017/00
출원번호
UP-0647901
(2006-12-28)
등록번호
US-7687558
(2010-04-23)
발명자
/ 주소
Cruse, Richard W.
York, W. Michael
Pohl, Eric R.
Chaves, Antonio
Joshi, Prashant
출원인 / 주소
Momentive Performance Materials Inc.
대리인 / 주소
Vicari, Dominick G.
인용정보
피인용 횟수 :
7인용 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 composition comprising from about 30 to about 99 weight percent of a silated cyclic core polysulfide of the general formula I: [Y1R1Sx-]m[G1(SR2SiX1X2X3)a]n[G2]o[R3Y2]p (I) wherein: each occurrence of G1 is independently selected from a polyvalent h
The invention claimed is: 1. A composition comprising from about 30 to about 99 weight percent of a silated cyclic core polysulfide of the general formula I: [Y1R1Sx-]m[G1(SR2SiX1X2X3)a]n[G2]o[R3Y2]p (I) wherein: each occurrence of G1 is independently selected from a polyvalent hydrocarbon 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 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 in Formula I 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), alkoxy (—OR6), hydrogen, carboxylic acid, and ester (—C(═O)OR6) wherein R6 is a monovalent hydrocarbon group having from 1 to 20 carbon atoms; each occurrence of R2 is independently selected from divalent hydrocarbon fragment having from 1 to 20 carbon atoms; each occurrence of R4 is independently selected from a polyvalent cyclic hydrocarbon fragment of 3 to about 28 carbon atoms or a polyvalent cyclic heterocarbon fragment of 3 to about 27 carbon atoms that was obtained by substitution of hydrogen atoms equal to the sum of a+c+e: each occurrence of R5 is independently selected from a polyvalent hydrocarbon fragment of 1 to about 28 carbon atoms or a polyvalent cyclic heterocarbon fragment of 1 to about 27 carbon atoms that was obtained by substitution of hydrogen atoms equal to the sum of c+e; 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, 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; 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 about 70 to about 1 weight percent of a silane of the general formula (II): [X1X2X3SiR1SxR3SiX1X2X3] (II) wherein each occurrence of R1 and R3 is independently selected from a divalent hydrocarbon fragment having from 1 to about 20 carbon atoms that include branched and straight chain alkyl, alkenyl, alkynyl, aryl or aralkyl groups wherein one hydrogen atom was substituted with a (—SiX1X2X3)group; each occurrence of X1 in Formula II 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, X1, and —OSi containing groups that result from the condensation of silanols; and x is 1 to about 10. 2. The composition of claim 1 wherein in the silated cyclic core polysulfide of Formula I R1 and R3 are branched or straight chain alkyl, alkenyl, alkynyl, aryl or aralkyl groups in which one hydrogen atom is substituted with a Y1 or Y2 group. 3. The composition of claim 1 wherein in the silated cyclic core polysulfide of Formula I R6 is branched or straight chain alkyl, alkenyl, aryl or aralkyl. 4. The composition of claim 1 wherein in the silated cyclic core polysulfide of Formula I R4 is cyclic or polycyclic alkyl, alkenyl, alkynyl, aryl, or aralkyl in which a+c+e−1 hydrogens have been replaced. 5. The composition of claim 1 wherein in the silated cyclic core polysulfide of Formula I R4 and R5 are polyvalent heterocarbon fragments from 3 to 27 carbon atoms. 6. The composition of claim 1 wherein in the silated cyclic core polysulfide of Formula I R5 is cyclic or polycyclic alkyl, alkenyl, alkynyl, aryl, or aralkyl in which a+c+e−1 hydrogens have been replaced. 7. The composition of claim 1 wherein in the silated cyclic core polysulfide of Formula I the heteroatom of R4 and R5 is selected from the group consisting of sulfur, oxygen, nitrogen, and mixtures thereof. 8. The composition of claim 1 wherein in the silated cyclic core polysulfide of Formula I the cyclic or polycyclic alkyl, alkynyl, aryl, aralkyl and arenyl of R4 in which a+c+e−1 hydrogens have been replaced is selected from the group consisting of ethylidenyl norbornane, ethylidene norbornyl, ethylidenyl norbornene, ethylidene norbornenyl, phenyl, naphthalenyl, benzyl, phenethyl, tolyl, xylyl, norbornyl, norbornenyl, ethylnorbornyl, ethylnorbornenyl, cyclohexyl, ethylcyclohexyl, ethylcyclohexenyl, cyclohexylcyclohexyl, and cyclododecatrienyl. 9. The composition of claim 1 wherein in the silated cyclic core polysulfide of Formula I the cyclic alkyl, alkynyl, aryl, aralkyl and arenyl of R5 in which c+e−1 hydrogens have been replaced is selected from the group consisting of ethylidenyl norbornane, ethylidene norbornyl, ethylidenyl norbornene, ethylidene norbornenyl, phenyl, naphthalenyl, benzyl, phenethyl, tolyl, xylyl, norbornyl, norbornenyl, ethylnorbornyl, ethylnorbornenyl, cyclohexyl, ethylcyclohexyl, ethylcyclohexenyl, cyclohexylcyclohexyl, and cyclododecatrienyl. 10. The composition of claim 1 wherein in the silated cyclic core polysulfide of Formula I the cyclic structure of R4, R5, and R6 is selected from the group consisting of bicyclic, tricyclic, higher cyclic structures, cyclic structures substituted with alkyl, alkenyl, and/or alkynyl groups. 11. The composition of claim 1 wherein in the silated cyclic core polysulfide of Formula I X1 is selected from the group of methoxy, ethoxy, propoxy, isopropoxy, butoxy, phenoxy, benzyloxy, hydroxy, chloro, and acetoxy. 12. The composition of claim 1 wherein in the silated cyclic core polysulfide of Formula I X2 and X3 are selected from the group consisting of methoxy, ethoxy, propoxy, isopropoxy, butoxy, phenoxy, benzyloxy, hydroxy, chloro, acetoxy, hydrogen, methyl, ethyl, propyl, isopropyl, sec-butyl, phenyl, vinyl, cyclohexyl, straight-chain alkyl, butyl, hexyl, octyl, lauryl, and octadecyl. 13. The composition of claim 1 wherein in the silated cyclic core polysulfide of Formula I R1 and R3 are terminal straight-chain alkyls substituted terminally at the end with —CH2—, —CH2CH2—, —CH2CH2CH2—, —CH2CH2CH2CH2CH2CH2CH2CH2—, beta-substituted analogs, and mixtures thereof. 14. The composition of claim 1 wherein in the silated cyclic core polysulfide of Formula I the beta substituted analog is —CH2(CH2)uCH(CH3)—, where u is zero to 17. 15. The composition of claim 1 wherein in the silated cyclic core polysulfide of Formula I R1 and R3 are structures derived from methallyl chloride, divinylbenzene, diallylether, butadiene, piperylene, isoprene, diradicals, limonene, monovinyl-containing structures derived from trivinylcyclohexane, monounsaturated structures derived from myrcene containing a trisubstituted C═C, monounsaturated structures derived from myrcene lacking a trisubstituted C═C, and mixtures thereof. 16. The composition of claim 1 wherein in the silated cyclic core polysulfide of Formula I G1 is selected from the group consisting of structures derivable from divinylbenzene, such as —CH2CH2(C6H4)CH(CH2—)—, —CH2CH2(C6H3—)CH2CH2—, and —CH2(CH—)(C6H4)CH(CH2—)—, where the notation C6H4 denotes a disubstituted benzene ring and C6H3— denotes a trisubstituted ring. 17. The composition of claim 1 wherein in the silated cyclic core polysulfide of Formula I G1 is derived from trivinylcyclohexane, such as —CH2(CH—)(vinylC6H9)CH2CH2—, (—CH2CH2)3C6H9, (—CH2CH2)2C6H9CH(CH3)—, —CH2(CH—)(vinylC6H9)(CH—)CH2—, —CH2CH2C6H9[(CH—)CH2]2, —CH(CH3)C6H9[(CH—)CH2—]2, C6H9[(CH—)CH2—]3, —CH2(CH—)C6H9[CH2CH2—]2, and —CH2(CH—)C6H9[CH(CH3)—][CH2CH2—], where the notation C6H9 denotes any isomer of the trisubstituted cyclohexane ring. 18. The composition of claim 1 wherein in the silated cyclic core polysulfide of Formula I G2 is derived from divinylbenzene, such as —CH2CH2(C6H4)CH2CH2—, —CH2CH2(C6H4)CH(CH2—)— and —CH2CH2(C6H3—)CH2CH2—, —CH2(CH—)(C6H4)CH(CH2—)—, where the notation C6H4 denotes a disubstituted benzene ring. 19. The composition of claim 1 wherein in the silated cyclic core polysulfide of Formula I G2 is selected from structures derivable from trivinylcyclohexane, such as —CH2CH2(vinylC6H9)CH2CH2—, (—CH2CH2)C6H9CH2CH3, —CH2(CH—)(vinylC6H9)CH2CH2—, (—CH2CH2)3C6H9, (—CH2CH2)2C6H9CH(CH3)—, —CH2(CH—)(vinylC6H9)(CH—)CH2—, —CH2CH2C6H9[(CH—)CH2—]2, —CH(CH3)C6H9[(CH—)CH2—]2, C6H9[(CH—)CH2—]3, —CH2(CH—)C6H9[CH2CH2—]2, and —CH2(CH—)C6H9[CH(CH3)—][CH2CH2—], where the notation C6H9 denotes any isomer of the trisubstituted cyclohexane ring. 20. The composition of claim 1 wherein in the silated cyclic core polysulfide of Formula I is any of the isomers of 4-(6-triethoxysilyl-3-thiahexyl)-1,2-bis-(13-triethoxysilyl-3,4,5,6-tetrathiamidecyl)cyclohexane; 4-(6-triethoxysilyl-3-thiahexyl)-1,2-bis-(13-triethoxysilyl-3,4-dithiamidecyl)cyclohexane; 4-(6-triethoxysilyl-3-thiahexyl)-1,2-bis-(13-triethoxysilyl-3,4,5-trithiamidecyl)cyclohexane; 4-(6-triethoxysilyl-3-thiahexyl)-1,2-bis-(12-triethoxysilyl-3,4,5-tetrathiadodecyl)cyclohexane; 1-(6-triethoxysilyl-3-thiahexyl)-2,4-bis-(11-triethoxysilyl-3,4-tetrathiaunidecyl)cyclohexane 4-(3-triethoxysilyl-1-thiaethyl)-1,2-bis-(13-triethoxysilyl-3,4,5,6,7-pentathiamidecyl)cyclohexane; 4-(6-diethoxymethylsilyl-2-thia hexyl)-1,2-bis-(13-triethoxysilyl-3,4,5,6-tetrathiamidecyl)cyclohexane; 4-(4-triethoxysilyl-2-thiabutyl)-1,2-bis-(9-triethoxysilyl-3,4,5,6-tetrathianonyl)cyclohexane; 4-(7-triethoxysilyl-3-thiaheptyl)-1,2-bis-(9-triethoxysilyl-3,4,5-trithianonyl)cyclohexane; 4-(5-triethoxysilyl-2-thiapentyl)-1,2-bis-(9-triethoxysilyl-3,4,5,6-tetrathianonyl)benzene; 4-(5-triethoxysilyl-2-thiapentyl)-1,2-bis-(9-triethoxysilyl-3,4,5-trithianonyl)benzene; 4-(5-triethoxysilyl-2-thiapentyl)-1,2-bis-(9-triethoxysilyl-3,4-dithianonyl)benzene; bis-2-[4-(3-triethoxysilyl-2-thiapropyl)-3-(9-triethoxysilyl-3,4,5,6-tetrathianonyl)cyclohexyl]ethyl tetrasulfide; bis-2-[4-(3-triethoxysilyl-1-thiapropyl)-3-(9-triethoxysilyl-3,4,5,6-tetrathianonyl)cyclohexyl]ethyl trisulfide; bis-2-[4-(3-triethoxysilyl-1-thiapropyl)-3-(7-triethoxysilyl-3,4-dithiaheptyl)cyclohexyl]ethyl disulfide; bis-2-[4-(6-triethoxysilyl-3-thiahexyl)-3-(9-triethoxysilyl-3,4,5-trithianonyl)phenyl]ethyl tetrasulfide; bis-2-[4-(6-triethoxysilyl-3-thiahexyl)-3-(9-triethoxysilyl-3,4,5-trithianonyl)nathyl]ethyl tetrasulfide; bis-2-[4-(4-diethoxymethylsilyl-2-thiabutyl)-3-(9-triethoxysilyl-3,4,5,6-tetrathianonyl)phenyl]ethyl trisulfide; bis-2-[4-(4-triethoxysilyl-2-thiaethyl)-3-(7-triethoxysilyl-3,4-dithiaheptyl)cycloheptyl]ethyl disulfide; bis-2-[4-(4-triethoxysilyl-2-thiaethyl)-3-(7-triethoxysilyl-3,4-dithiaheptyl)cyclooctyl]ethyl disulfide; bis-2-[4-(4-triethoxysilyl-2-thiaethyl)-3-(7-triethoxysilyl-3,4-dithiaheptyl)cyclododecyl]ethyl disulfide; 4-(6-triethoxysilyl-3-thiahexyl)-1,2-bis-(9-triethoxysilyl-3,4,5,6-tetrathianonyl)cyclohexane; 2-(6-triethoxysilyl-3-thiahexyl)-1,4-bis-(9-triethoxysilyl-3,4,5,6-tetrathianonyl)cyclohexane; 1-(6-triethoxysilyl-3-thiahexyl)-2,4-bis-(9-triethoxysilyl-3,4,5,6-tetrathianonyl)cyclohexane; 4-(6-triethoxysilyl-3-thiahexyl)-1,2-bis-(7-triethoxysilyl-3,4-dithiaheptyl)cyclohexane; 2-(6-triethoxysilyl-3-thiahexyl)-1,4-bis-(7-triethoxysilyl-3,4-dithiaheptyl)cyclohexane; 1-(6-triethoxysilyl-3-thiahexyl)-2,4-bis-(7-triethoxysilyl-3,4-dithiaheptyl)cyclohexane, and mixtures thereof. 21. The composition of claim 1 wherein in the silated cyclic core polysulfide of Formula I R1 and R3 are independently selected from a divalent hydrocarbon fragment having from 1 to about 5 carbon atoms. 22. The composition of claim 1 wherein in the silated cyclic core polysulfide of Formula I R1 and R3 are branched and/or straight chain alkyl, alkenyl or alkynyl groups in which one hydrogen atom was substituted with a Y1 or Y2 group. 23. The composition of claim 1 wherein in the silated cyclic core polysulfide of Formula I Y1 and Y2 are silyl (—SiX1X2X3), hydrogen, alkoxy (—OR6), carboxylic acid, ester (—C(═O)OR6) wherein R6 is a monovalent hydrocarbon group having from 1 to 5 carbon atoms. 24. The composition of claim 1 wherein in the silated cyclic core polysulfide of Formula I R2 is a straight chain hydrocarbon represented by —(CH2)f— where f is an integer from about 1 to about 5. 25. The composition of claim 1 wherein in the silated cyclic core polysulfide of Formula I R4 is a polyvalent hydrocarbon fragment of 5 to about 12 carbon atoms. 26. The composition of claim 1 wherein in the silated cyclic core polysulfide of Formula I R5 is a polyvalent hydrocarbon fragment of 5 to about 12 carbon atoms. 27. The composition of claim 1 wherein in the silated cyclic core polysulfide of Formula I 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. 28. The composition of claim 1 wherein in the silated cyclic core polysulfide of Formula I 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, wherein R6 is a monovalent hydrocarbon group having from 1 to 5 carbon atoms, and —OSi containing groups that result from the condensation of silanols. 29. The composition of claim 1 wherein in the silated cyclic core polysulfide of Formula I 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 5; m and p are 1, n is 1 to about 10; o is 0 to about 1; and x is 1 to about 6. 30. The composition of claim 1 wherein the silane of Formula II is selected from the group consisting of bis-(3-triethoxysilylpropyl)disulfide; bis-(3-triethoxysilylpropyl)trisulfide; bis-(3-triethoxysilylpropyl)tetrasulfide; bis-(3-triethoxysilylpropyl)pentasulfide; bis-(3-diethoxymethylsilylpropyl)disulfide; bis-(3-ethoxydimethylsilylpropyl)disulfide; bis-(triethoxysilylmethyl) disulfide; bis-(4-triethoxysilylbenzyl)disulfide, bis-(3-triethoxysilylphenyl)disulfide, and mixtures thereof. 31. A process for making a composition comprising from about 30 to about 99 weight percent of a silated cyclic core polysulfide from about 1 to about 70 weight percent of a silated according to claim 1 which comprises: (a) reacting a thioacid with the structure, R6C(═O)SH with a hydrocarbon containing reactive double bonds, wherein R6 is a monovalent hydrocarbon group having from 1 to 20 carbon atoms; (b) deblocking the mercapto group using a proton donator; (c) reacting the intermediate mercaptan in step (b) with a base and then a halo containing hydrocarbon silane; (d) reacting the intermediate mercapto silane from step (c) with a base and sulfur; (e) reacting the intermediate in step (d) with a substituted or unsubstituted hydrocarbon containing a leaving group selected from chlorine, bromine or iodine, and mixtures thereof. 32. The process of claim 31 wherein the process is carried out in an organic solvent. 33. The process of claim 32 wherein the organic solvent is selected from the group consisting of ethanol, methanol, isopropyl alcohol, tetrahydrofuran, diethyl ether, hexanes, cyclohexane, toluene, xylenes, and mixtures thereof. 34. The process of claim 31 wherein the hydrocarbon containing at least one double bond in step (a) has the general formula: wherein R4 is independently selected from a polyvalent hydrocarbon fragment of 1 to about 28 carbon atoms and the subscripts g, h and i are about 0 to 3. 35. The process of claim 31 wherein the free radical agent of step (b) is an oxidizing agent that converts thiocarboxylic acid to a thiocarboxylic acid radical. 36. The process of claim 35 wherein the oxidizing agent is selected from the group consisting of oxygen, peroxides, hydroperoxides, and mixtures thereof. 37. The process of claim 36 wherein the proton donator of step (c) is a hydrogen containing heterocarbon or substituted heterocarbon that is capable of reacting with the intermediate of step (b). 38. The process of claim 31 wherein the proton donor is selected from the group consisting of alcohols, amines, mercaptans, and mixtures thereof. 39. The process of claim 38 wherein the alcohol is selected from the group consisting of methanol, ethanol, isopropyl alcohol, propanol, and mixtures thereof. 40. The process of claim 38 wherein the amine is selected from the group consisting of ammonia, methyl amine, propyl amine, diethanol amine, and mixtures thereof. 41. The process of claim 38 wherein the mercaptan is selected from the group consisting of propyl mercaptans, butyl mercaptan, and mixtures thereof. 42. The process of claim 31 wherein the substituted or unsubstituted hydrocarbon of step (e) has the general formulae selected from the group consisting of: Y1R1Z; or Y2R3Z; wherein each occurrence of Y1 and Y2, is independently silyl (—SiX1X2X3), R1and R3 are independently selected from a divalent hydrocarbon fragment having from 1 to about 20 carbon atoms, and Z is selected from the group consisting of Cl, Br and I, and mixtures thereof. 43. The process of claim 31 wherein the silated cyclic core polysulfide is any of the isomers of 4-(6-triethoxysilyl-3-thiahexyl)-1,2-bis-(13-triethoxysilyl-3,4,5,6-tetrathiamidecyl)cyclohexane; 4-(6-triethoxysilyl-3-thiahexyl)-1,2-bis-(13-triethoxysilyl-3,4-dithiamidecyl)cyclohexane; 4-(6-triethoxysilyl-3-thiahexyl)-1,2-bis-(13-triethoxysilyl-3,4,5-trithiamidecyl)cyclohexane; 4-(6-triethoxysilyl-3-thiahexyl)-1,2-bis-(12-triethoxysilyl-3,4,5-tetrathiadodecyl)cyclohexane; 1-(6-triethoxysilyl-3-thiahexyl)-2,4-bis-(11-triethoxysilyl-3,4-tetrathiaunidecyl)cyclohexane 4-(3-triethoxysilyl-1-thiaethyl)-1,2-bis-(13-triethoxysilyl -3,4,5,6,7-pentathiamidecyl)cyclohexane; 4-(6-diethoxymethylsilyl-2-thia hexyl)-1,2-bis-(13-triethoxysilyl-3,4,5,6-tetrathiamidecyl)cyclohexane; 4-(4-triethoxysilyl-2-thiabutyl)-1,2-bis-(9-triethoxysilyl-3,4,5,6-tetrathianonyl)cyclohexane; 4-(7-triethoxysilyl-3-thiaheptyl)-1,2-bis-(9-triethoxysilyl-3,4,5-trithianonyl)cyclohexane; 4-(5-triethoxysilyl-2-thiapentyl)-1,2-bis-(9-triethoxysilyl-3,4,5,6-tetrathianonyl)benzene; 4-(5-triethoxysilyl-2-thiapentyl)-1,2-bis-(9-triethoxysilyl-3,4,5-trithianonyl)benzene; 4-(5-triethoxysilyl-2-thiapentyl)-1,2-bis-(9-triethoxysilyl-3,4-dithianonyl)benzene; bis-2-[4-(3-triethoxysilyl-2-thiapropyl)-3-(9-triethoxysilyl-3,4,5,6-tetrathianonyl)cyclohexyl]ethyl tetrasulfide; bis-2-[4-(3-triethoxysilyl-1-thiapropyl)-3-(9-triethoxysilyl-3,4,5,6-tetrathianonyl)cyclohexyl]ethyl trisulfide; bis-2-[4-(3-triethoxysilyl-1-thiapropyl)-3-(7-triethoxysilyl-3,4-dithiaheptyl)cyclohexyl]ethyl disulfide; bis-2-[4-(6-triethoxysilyl-3-thiahexyl)-3-(9-triethoxysilyl-3,4,5-trithianonyl)phenyl]ethyl tetrasulfide; bis-2-[4-(6-triethoxysilyl-3-thiahexyl)-3-(9-triethoxysilyl-3,4,5-trithianonyl)nathyl]ethyl tetrasulfide; bis-2-[4-(4-diethoxymethylsilyl-2-thiabutyl)-3-(9-triethoxysilyl-3,4,5,6-tetrathianonyl)phenyl]ethyl trisulfide; bis-2-[4-(4-triethoxysilyl-2-thiaethyl)-3-(7-triethoxysilyl -3,4-dithiaheptyl)cycloheptyl]ethyl disulfide; bis-2-[4-(4-triethoxysilyl-2-thiaethyl)-3-(7-triethoxysilyl-3,4-dithiaheptyl)cyclooctyl]ethyl disulfide; bis-2-[4-(4-triethoxysilyl-2-thiaethyl) -3-(7-triethoxysilyl-3,4-dithiaheptyl)cyclododecyl]ethyl disulfide; 4-(6-triethoxysilyl-3-thiahexyl)-1,2-bis-(9-triethoxysilyl-3,4,5,6-tetrathianonyl)cyclohexane; 2-(6-triethoxysilyl-3-thiahexyl)-1,4-bis-(9-triethoxysilyl-3,4,5,6-tetrathianonyl)cyclohexane; 1-(6-triethoxysilyl-3-thiahexyl)-2,4-bis-(9-triethoxysilyl-3,4,5,6-tetrathianonyl)cyclohexane; 4-(6-triethoxysilyl-3-thiahexyl)-1,2-bis-(7-triethoxysilyl-3,4-dithiaheptyl)cyclohexane; 2-(6-triethoxysilyl-3-thiahexyl)-1,4-bis-(7-triethoxysilyl-3,4-dithiaheptyl)cyclohexane; 1-(6-triethoxysilyl-3-thiahexyl)-2,4-bis-(7-triethoxysilyl-3,4-dithiaheptyl)cyclohexane, and mixtures thereof.
연구과제 타임라인
LOADING...
LOADING...
LOADING...
LOADING...
LOADING...
이 특허에 인용된 특허 (106)
Cohen Martin Paul (Fairlawn OH) Losey Cheryl Ann (Kent OH) Parker Dane Kenton (Massillon OH), Aminosilane compounds in silica-filled rubber compositions.
Schwarz Rudolf (Alzenau-Wasserlos DEX) Kleinschmit Peter (Hanau DEX) Liedtke Christa (Bruchkbel DEX) Wolff Siegfried (Bornheim-Merten DEX), Bis-(silylethyl)-oligosulphides and process for their production.
Schwarz Rudolf (Alzenau-Wasserlos DEX) Kleinschmit Peter (Hanau DEX) Liedtke Christa (Bruchkbel DEX) Wolff Siegfried (Bornheim-Merten DEX), Bis-(silylethyl)-oligosulphides and process for their production.
Wolff Siegfried (Bornheim-Merten DEX) Grl Udo (Meckenheim DEX), Carbon blacks modified with organosilicon compounds, method of their production and their use in rubber mixtures.
Pochert Johannes (Walberberg DT) Wolff Siegfried (Bornheim-Merten DT) Thurn Friedrich (Rodenkirchen DT), Compositions containing silica, a phenoplast or an aminoplast, and a silane.
Wolff Siegfried (Bornheim-Merten DEX) Tan Ewe H. (Wesseling-Berzdorf DEX), Cross-linkable rubber mixtures containing silicate fillers and process for cross-linking.
Waldman Bruce A. ; Huang Misty Weiyu ; Cruse Richard W., Elastomeric composition comprising a blocked mercaptosilane coupling agent and a deblocking agent.
Wolff Siegfried (Bornheim-Merten DEX) Gorl Udo (Meckenheim DEX) Deusser Hans (Karlstein DEX), Method for the production of fillers modified with organosilicon compounds, the fillers produced in this manner and thei.
Gorl Udo,DEX ; Lambertz Horst,DEX, Mixture of organosilanepolysulphanes and a process for the production of rubber compounds containing these mixtures.
Kerner Dieter (Hanau DEX) Kleinschmit Peter (Hanau DEX) Parkhouse Alan (Wesseling DEX) Wolff Siegfried (Bornheim-Merten DEX), Natural oxidic or silicate filler modified on the surface, a process for its production.
Batz-Sohn Christoph,DEX ; Luginsland Hans-Detlef,DEX, Oligomeric organosilicon compounds, their use in rubber mixtures and for the production of shaped articles.
Yoshioka Hiroshi (Annaka JPX) Ono Ichiro (Annaka JPX) Uehara Hitoshi (Matsuida JPX), Organosilicon compound having polysulfide linkages and a rubber composition comprising the same.
Musleve Richard Thomas (Akron OH) Parker Dane Kenton (Massillon OH) Hirst Robert Charles (Akron OH), Preparation of sulfur-containing organosilicon compounds.
Parker Dane K. (Massillon OH) Musleve Richard T. (Akron OH) Hirst Robert C. (Akron OH) Hopper Roger J. (Akron OH), Preparation of sulfur-containing organosilicon compounds.
Michel Rudolf,DEX ; Munzenberg Jorg,DEX, Process for the preparation of mixtures of organosilicon oligosulfanes containing a high proportion of organosilicon disulfanes.
Cohen Martin Paul (Fairlawn OH) Parker Dane Kenton (Massillon OH) Wideman Lawson Gibson (Tallmadge OH), Process for the preparation of organosilicon disulfide compounds.
Wideman Lawson Gibson (Tallmadge OH) Folk Theodore Lamson (Cuyahoga Falls OH) Cohen Martin Paul (Fairlawn OH), Process for the preparation of organosilicon polysulfide compounds.
Childress Thomas E. (Newport OH) Ritscher James S. (Marietta OH) Schilling ; Jr. Curtis L. (Marietta OH) Tucker ; Jr. Okey G. (Vienna WV) Beddow Donald G. (Waverly WV), Process for the preparation of silane polysulfides.
Wolff Siegfried (Bornheim-Merten DEX) Goerl Udo (Bornheim-Roisdorf DEX), Process for the production of plastic and rubber compositions filled with carbon black.
Buder ; Wolfgang ; Pletka ; Hans-Dieter ; Michel ; Rudolf ; Schwarz ; Ru dolf ; Dusing ; Gerhard, Process for the production of sulfur containing organosilicon compounds.
Panster Peter (Rodenbach DEX) Michel Rudolf (Freigericht DEX) Kleinschmit Peter (Hanau DEX) Deschler Ulrich (Hanau DEX), Process for the production of sulfur containing organosilicon compounds.
Bradshaw Jerald S. (Provo UT) Tarbet Byron J. (Provo UT) Krakowiak Krzysztof E. (Provo UT) Biernat Jan F. (Provo UT) Bruening Ronald L. (Provo UT) Izatt Reed M. (Provo UT), Process of removing ions from solutions by forming a complex with a sulfur containing hydrocarbon covalently bonded to s.
Penot,Christophe; Roy,Vanessa, Rubber composition for a tire comprising a reinforcing inorganic filler and an (inorganic filler/elastomer) coupling system.
Bomal Yves,FRX ; Durel Olivier,FRX, Rubber composition for tire casings based on silicas containing a reinforcing additive based on a functionalized polyorganosiloxane and on an organosilane compound.
Korth,Karsten; Eichenauer,Kurt; Pieter,Reimund; Klockmann,Oliver; Heidlas,J?rgen; Ober,Martin; Zobel,Rudolf, Silane-modified oxidic or siliceous filler, process for its production and its use.
Agostini Giorgio (Colmar-Berg LUX) Frank Uwe Ernst (Ettelbruck LUX) Materne Thierry Florent Edme (Attert BEX) Visel Friedrich (Bofferdange LUX) Zimmer ReneJean (Howald LUX), Silica reinforced rubber composition and use in tires.
Corvasce Filomeno Gennaro (Mertzig ITX) Linster Tom Dominique (Gilsdorf LUX) Thielen Georges (Ettelbruck LUX), Starch composite reinforced rubber composition and tire with at least one component thereof.
Schwarze Werner (Frankfurt am Main DEX) Wolff Siegfried (Bornheim-Merten DEX) Lambertz Horst (Hrth DEX), Substituted N-trichloromethyl thiodicarboximides and N,N-substituted bis-(2,4-diamino-s-triazin-6-yl)-oligosulfides in v.
Pletka Hans-Dieter (Mobile AL) Zezulka Gerd (Hanau DEX), Sulfur and phosphorus containing organosilicon compounds and process for their production and use.
Meyer-Simon Eugen (Frankfurt DT) Schwarze Werner (Frankfurt DT) Thurn Friedrich (Grossauheim DT) Michel Rudolf (Somborn DT), Sulfur containing organosilicon compounds.
Seiler Claus-Dietrich (Rheinfelden DT) Vahlensieck Hans-Joachim (Wehr DT) Amort Jurgen (Troisdorf-Sieglar DT), Sulfurous organic silicon compounds, a process for their preparation, and their use as adhesivizing agents.
Kerner Dieter (Hanau DEX) Kleinschmit Peter (Hanau DEX) Parkhouse Alan (Wesseling DEX) Wolff Siegfried (Bornheim-Merten DEX), Surface modified synthetic, silicatic filler, a process for its production and its use.
Wideman Lawson Gibson ; Zanzig David John ; Evans Theodore Augustus ; Sun Charlie, Unsaturated amine-functional silane compounds and their use in rubber compositions.
York, W. Michael; Cruse, Richard W.; Recker, Carla; Pohl, Eric Raymond; Joshi, Prashant G., Tire compositions and components containing blocked mercaptosilane coupling agent.
York, W. Michael; Cruse, Richard W.; Jaeckel, Janna; Pohl, Eric Raymond; Joshi, Prashant G., Tire compositions and components containing free-flowing filler compositions.
York, W. Michael; Cruse, Richard W.; Pohl, Eric Raymond; Joshi, Prashant G., Tire compositions and components containing free-flowing filler compositions.
York, W. Michael; Cruse, Richard W.; Jaeckel, Janna; Pohl, Eric Raymond; Joshi, Prashant G., Tire compositions and components containing silated cyclic core polysulfides.
※ AI-Helper는 부적절한 답변을 할 수 있습니다.