# US 4,395,507 A · Self-bonding one-component dimedone RTV silicone rubber compositions > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,395,507 A - Document ID: US4395507A - Status: Granted - Kind: A - Application number: 06/331,232 - Filed: 1981-12-16 - Granted: 1983-07-26 - Earliest claimed: 1981-12-16 - Assignees: General Electric Silicones - Inventors: John J. Dziark; Kazuto Shinohara - Web page: https://patentgrep.com/patent/US4395507A ## CPC - C08K 5/54: Silicon-containing compounds {(C08K5/0091 takes precedence)} - C08K 5/57: Organo-tin compounds - C08L 83/04: Polysiloxanes - C08G 77/16: to hydroxy groups - C08G 77/18: to alkoxy or aryloxy groups - C08G 77/24: halogen-containing groups - C08G 77/28: sulfur-containing groups - C08G 77/70: {Siloxanes defined by use of the MDTQ nomenclature} - Y10T 428/31663: As siloxane, silicone or silane - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION ## Abstract The present invention relates to dimedone functional self-bonding room temperature vulcanizable silicone rubber compositions. The self-bond additive is selected from silyl maleates, silyl fumarates, silyl succinates, silyl isocyanurates and mixtures thereof. Preferably the self-bonding additive is prereacted with the cross-linking agent before they are incorporated into the RTV composition. This prereaction of the self-bonding additive and the cross-linking agent imparts shelf-stability to the composition. ## Claims ### Claim 1 A self-bonding one-component RTV silicone rubber composition comprising (A) 100 parts by weight of an organopolysiloxane consisting essentially of chemically combined units of the formula, ##STR27## and having terminal alkoxysiloxy units of the formula, ##STR28## where R is a C.sub.(1-13) monovalent organic radical, R.sup.1 is selected from hydrogen, halogen and R, R.sup.2 is a C.sub.(1-8) alkyl radical, X and Y are divalent radicals selected from --O--, --S--, and ##STR29## Z is a divalent C.sub.(1-13) organic radical selected from alkylene, cycloalkylene, arylene and a fused ring structure, b and c are equal to 0 or 1, R.sup.3 is selected from hydrogen and R, e is a whole number having a value of 0 or 1, g is equal to 1 or 2, and the sum of e+g is equal to 1 or 2; (B) from 3 to 8 parts by weight of an adhesion promoter which is selected from the class consisting of silyl maleates, silyl fumarates, silyl succinates, silyl isocyanurates and mixtures thereof. ### Claim 2 (depends on 1) The composition of claim 1 where R is a mixture of methyl and 3,3,3, trifluoropropyl radicals. ### Claim 3 (depends on 2) The composition of claim 2 wherein the adhesion promoter is bis(3-trimethoxysilylpropyl) maleate. ### Claim 4 (depends on 2) The composition of claim 2 wherein the adhesion promoter is 1,3,5-tris(3-trimethoxysilylpropyl) isocyanurate. ### Claim 5 (depends on 2) The composition of claim 2 wherein the adhesion promoter is bis(3-trimethoxysilylpropyl) fumarate. ### Claim 6 (depends on 1) The composition of claim 1 wherein there is further present from 0.01 to 10 parts by weight of a curing promoter which is metal salt of a carboxylic acid. ### Claim 7 (depends on 2) The composition of claim 2 wherein the curing promoter is a tin salt. ### Claim 8 (depends on 7) The composition of claim 7 wherein the tin salt is dimethyl tin bis-neodecanoate. ### Claim 9 (depends on 6) The composition of claim 6 wherein the curing promoter is dibutyl tin diacetate. ### Claim 10 (depends on 9) The composition of claim 9 wherein there is present from 10 to 200 parts by weight of a filler. ### Claim 11 (depends on 10) The composition of claim 10 wherein the filler is fumed silica treated with cyclopolysiloxanes. ### Claim 12 (depends on 11) The composition of claim 11 wherein there is further present from 0 to 40 parts by weight of a first plasticizer which is a linear diorganopolysiloxane polymer of a viscosity varying from 10 to 20,000 centipoise at 25.degree. C. and the organo group is a C.sub.(1-8) monovalent hydrocarbon radical. ### Claim 13 (depends on 12) The composition of claim 12 wherein there is further present from 0.2 to 10 parts by weight of a second plasticizer and adhesion promoter which is silanol containing diorganopolysiloxane with a viscosity in the range of 10 to 1000 centipoise at 25.degree. C. where the organo group is a C.sub.(1-8) monovalent hydrocarbon radical and the silanol content varies from 3 to 10% by weight. ### Claim 14 (depends on 1) The composition of claim 1 wherein there is present from 1 to 10 parts of iron oxide as a thermal stabilizer. ### Claim 15 A self-bonding one-component RTV silicone rubber composition comprising (A) 100 parts by weight of a silanol end-stopped polymer of the formula, ##STR30## where s varies such that the viscosity of the polymer varies from 100 to 1,000,000 centipoise at 25.degree. C. and the reaction product of (B) from 0.1 to 10 parts by weight of a silyl ether cross-linking agent of the formula, ##STR31## where Q is a hydrolyzable radical, R is a C.sub.(1-13) monovalent organic radical, R.sup.1 is selected from hydrogen, halogen, and R, R.sup.2 is a C.sub.(1-8) alkyl radical, X and Y are divalent radicals selected from --O--, --S-- and ##STR32## Z is a divalent C.sub.(1-13) organic radical selected from alkylene, cycloalkylene, arylene and a fused ring structure, b and c are equal to 0 or 1, R.sup.3 is selected from hydrogen and R, e is a whole number having a value of 0 or 1, g is equal to 1 or 2, and the sum of e+g is equal to 1 or 2; and (C) from 3 to 8 parts by weight of an adhesion promoter selected from the class consisting of silyl maleates, silyl fumarates, silyl succinates, silyl isocyanurates, and mixtures thereof. ### Claim 16 (depends on 15) The composition of claim 15 wherein the reaction product is formed by pre-reacting the cross-linking agent with the adhesion promoter at a temperature in the range of 40.degree. C.-120.degree. C. ### Claim 17 (depends on 16) The composition of claim 16 wherein the reaction product is formed by pre-reacting the cross-linking agent with adhesion promoter for a period of time varying from 2 hours to 10 days. ### Claim 18 (depends on 17) A composition of claim 17 wherein R is a mixture of methyl and 3,3,3-trifluoropropyl radicals. ### Claim 19 (depends on 18) The composition of claim 18 wherein the adhesion promoter is bis(3,trimethoxysilylpropyl) maleate. ### Claim 20 (depends on 18) The composition of claim 18 wherein the adhesive promoter is 1,3,5-tris(3-trimethoxysilylpropyl) isocyanurate. ### Claim 21 (depends on 18) The composition of claim 18 wherein the adhesion promoter is bis(3-trimethoxysilylpropyl) fumarate. ### Claim 22 (depends on 17) The composition of claim 17 wherein there is present from 1 to 10 parts by weight of iron oxide as a thermal stabilizer. ### Claim 23 (depends on 15) The composition of claim 15 wherein there is present from 0.01 to 10 parts by weight of a curing promoter which is a metal salt of a carboxylic acid. ### Claim 24 (depends on 23) The composition of claim 23 wherein the curing promoter is a tin salt. ### Claim 25 (depends on 24) The composition of claim 24 wherein the tin salt is a dimethyl tin bis-neodecanoate. ### Claim 26 (depends on 24) The composition of claim 24 wherein the tin salt is dibutyl tin diacetate. ### Claim 27 (depends on 26) The composition of claim 26 wherein there is present from 10 to 200 parts by weight of a filler. ### Claim 28 (depends on 27) The composition of claim 27 wherein the filler is fumed silica treated with cyclopolysiloxanes. ### Claim 29 (depends on 28) The composition of claim 28 where there is further present from 0 to 40 parts by weight of a first plasticizer which is a linear diorganopolysiloxane polymer of a viscosity varying from 10 to 20,000 centipoise at 24.degree. C. and the organo group is a C.sub.(1-8) monovalent hydrocarbon radical. ### Claim 30 (depends on 29) The composition of claim 29 wherein there is further present from 1 to 20 parts by weight of a second plasticizer and an adhesion promoter which is silanol containing diorganopolysiloxane with a viscosity in the range of 10 to 1,000 centipoise at 25.degree. C. where the organo group is a C.sub.(1-8) monovalent hydrocarbon radical and the silanol content varies from 3 to 10% by weight. ### Claim 31 A self-bonding one-component RTV silicone rubber composition comprising (A) 100 parts by weight of a base organopolysiloxane consisting essentially of chemically combined units of the formula ##STR33## and having terminal siloxy units of the formula, ##STR34## where R is a C.sub.(1-13) monovalent organic radical, R.sup.1 is selected from hydrogen, halogen and R, X and Y are divalent radicals selected from --O--, --S-- and ##STR35## Z is a divalent C.sub.(1-13) organic radical selected from alkylene, cycloalkylene, arylene and a fused ring structure, b and c are equal to 0 or 1, R.sup.3 is selected from hydrogen and R and d is a whole number having a value of 0 or 1, R.sup.5 is a C.sub.(1-13) monovalent organic radical, and (B) from 3 to 8 parts by weight of an adhesion promoter selected from a class consisting of silyl maleates, silyl fumarates, silyl succinates, silyl isocyanurates, and mixtures thereof. ### Claim 32 (depends on 31) A composition of claim 31 wherein R is a mixture of methyl and 3,3,3-trifluoropropyl radicals. ### Claim 33 (depends on 32) A composition of claim 32 wherein the adhesion promoter is bis(3-trimethoxysilylpropyl) maleate. ### Claim 34 (depends on 32) The composition of claim 32 wherein the adhesion promoter is 1,3,5-tris(3-trimethoxysilylpropyl) isocyanurate. ### Claim 35 (depends on 32) The composition of claim 32 wherein the adhesion promoter is bis(-3-trimethoxysilylpropyl) fumarate. ### Claim 36 (depends on 31) The composition of claim 31 wherein there is further present from 1 to 10 parts by weight of iron oxide as a heat stabilizer. ### Claim 37 (depends on 31) The composition of claim 31 wherein in the base organopolysiloxane, R.sup.5 is a C.sub.(4-12) alkyl radical. ### Claim 38 (depends on 37) The composition of claim 37 where R.sup.5 is a dodecyl radical. ### Claim 39 (depends on 38) The composition of claim 38 wherein there is further present from 0.01 to 10 parts by weight of a curing promoter which is a metal salt of carboxylic acid. ### Claim 40 (depends on 39) The composition of claim 39 wherein the curing promoter is dibutyl tin diacetate. ### Claim 41 (depends on 39) The composition of claim 39 wherein the curing promoter is a tin salt. ### Claim 42 (depends on 41) The composition of claim 41 wherein the tin salt is dimethyl tin bis-neodecanoate. ### Claim 43 (depends on 42) The composition of claim 42 wherein there is further present from 10 to 200 parts by weight of a filler. ### Claim 44 (depends on 43) The composition of claim 43 wherein this filler is fumed silica treated with cyclopolysiloxanes. ### Claim 45 (depends on 44) The composition of claim 44 wherein there is further present from 0 to 40 parts by weight of a first plasticizer which is a linear diorganopolysiloxane of a viscosity varying from 10 to 20,000 centipoise at 25.degree. C. and the organo group is C.sub.(1-8) monovalent hydrocarbon radical. ### Claim 46 (depends on 45) The composition of claim 45 wherein there is further present from 1 to 20 parts by weight of a second plasticizer and an adhesion promoter which is silanol containing diorganopolysiloxane with a viscosity in the range of 10 to 1000 centipoise at 25.degree. C. wherein the organo group is a C.sub.(1-8) monovalent hydrocarbon radical and the silanol content varies from 3 to 10% by weight. ### Claim 47 A self-bonding one-component RTV silicone rubber composition comprising (A) 100 parts by weight of a silanol end-stopped polymer of the formula, ##STR36## where s varies such that the viscosity of the polymer varies from 100 to 1,000,000 centipoise at 25.degree. C. and the reaction product of (B) from 0.1 to 10 parts by weight of a silyl ether cross-linking agent of the formula, ##STR37## where Q is a hydrolyzable radical, R is a C.sub.(1-13) monovalent organic radical, R.sup.1 is selected from hydrogen, halogen and R, X and Y are divalent radicals selected from --O--, --S-- and ##STR38## Z is a divalent C.sub.(1-13) organic radical selected from alkylene, cycloalkylene, arylene and a fused ring structure, b and c are equal to 0 or 1, R.sup.3 is selected from hydrogen and R, and d is a whole number having a value of 0 or 1, R.sup.5 is a C.sub.(1-13) monovalent organic radical; and (C) from 3 to 8 parts by weight of an adhesion promoter selected from the class consisting of silyl maleates, silyl fumarates, silyl succinates, silyl isocyanurates, and mixtures thereof. ### Claim 48 (depends on 47) The composition of claim 47 wherein the reaction product is formed by reacting the cross-linking agent with the adhesion promoter at a temperature in the range of 40.degree.-120.degree. C. ### Claim 49 (depends on 48) The composition of claim 48 wherein the reaction product is formed by reacting the cross-linking agent with the adhesion promoter for a period of time varying from 2 hours to 10 days. ### Claim 50 (depends on 47) The composition of claim 47 wherein R is a mixture of methyl and 3,3,-trifluoropropyl radicals. ### Claim 51 (depends on 50) The composition of claim 50 wherein the adhesion promoter is bis(3-trimethoxysilylpropyl) maleate. ### Claim 52 (depends on 50) The composition of claim 50 wherein the adhesion promoter is 1,3,5-tris(3-trimethoxysilylpropyl) isocyanurate. ### Claim 53 (depends on 50) The composition of claim 50 wherein the adhesion promoter is bis(3-trimethoxysilylpropyl) fumarate. ### Claim 54 (depends on 50) The composition of claim 50 wherein in the silyl ether cross-linking agent R.sup.5 is a C.sub.(4-12) alkyl radical. ### Claim 55 (depends on 54) The composition of claim 54 wherein there is further present from 0.01 to 10 parts by weight of a curing promoter which is a metal salt of a carboxylic acid. ### Claim 56 (depends on 55) The composition of claim 55 wherein the curing promoter is a tin salt. ### Claim 57 (depends on 56) The composition of claim 56 wherein the curing promoter is dibutyl tin diacetate. ### Claim 58 (depends on 57) The composition of claim 57 wherein there is further present from 1 to 10 parts by weight of iron oxide as a thermal stabilizer. ### Claim 59 (depends on 56) The composition of claim 56 wherein the tin salt is dimethyl tin bis-neodecanoate. ### Claim 60 (depends on 59) The composition of claim 59 wherein there is further present from 10 to 200 parts by weight of a filler. ### Claim 61 (depends on 60) The composition of claim 60 wherein the filler is fumed silica treated with cyclopolysiloxanes. ### Claim 62 (depends on 61) The composition of claim 61 wherein there is further present from 0 to 40 parts by weight of a first plasticizer which is a linear diorganopolysiloxane polymer of a viscosity varying from 10 to 20,000 centipoise at 25.degree. C. and the organo group is a C.sub.(1-8) monovalent hydrocarbon radical. ### Claim 63 (depends on 62) The composition of claim 62 wherein there is further present from 1 to 20 parts by weight of a second plasticizer and an additional adhesion promoter which is silanol containing diorganopolysiloxane with a viscosity in the range of 10 to 1,000 centipoise at 25.degree. C. where the organo group is a C.sub.(1-8) monovalent hydrocarbon radical and the silanol content varies from 3 to 10% by weight. ### Claim 64 A process for forming a self-bonding one-component RTV silicone rubber composition comprising (1) mixing (A) 100 parts by weight of a silanol end-stopped polymer of the formula, ##STR39## where s varies such that the viscosity of the polymer varies from 100 to 1,000,000 centipoise at 25.degree. C. with the reaction product of (B) from 0.1 to 10 parts by weight of a silyl ether cross-linking agent of the formula ##STR40## where Q is a hydrolyzable radical, R is a C.sub.(1-13) monovalent organic radical, R.sup.1 is selected from hydrogen, halogen, and R, R.sup.2 is a C.sub.(1-8) alkyl radical, X and Y are divalent radicals selected from --O--, --S-- and ##STR41## Z is a divalent C.sub.(1-13) organic radical selected from alkylene, cycloalkylene, arylene and a fused ring structure, b and c are equal to 0 or 1, R.sup.3 is selected from hydrogen and R, e is a whole number having a value of 0 or 1, g is equal to 1 or 2, and the sum of e+g is equal to 1 or 2; with (C) from 3 to 8 parts by weight of an adhesion promoter selected from the class consisting of silyl maleates, silyl fumarates, silyl succinates, silyl isocyanurates and mixtures thereof, and (2) allowing the composition to cure at room temperature. ### Claim 65 (depends on 64) The process of claim 64 wherein the reaction product is formed by reacting the cross-linking agent with the adhesion promoter at a temperature in the range of 40.degree.-120.degree. C. ### Claim 66 (depends on 65) The process of claim 65 wherein the reaction product is formed by reacting the cross-linking agent with the adhesion promoter for a period of time varying from 2 hours to 10 days. ### Claim 67 (depends on 66) The process of claim 66 wherein R is a mixture of methyl and 3,3,3-trifluoropropyl radicals. ### Claim 68 (depends on 67) The process of claim 67 wherein the adhesion promoter is bis(3-trimethoxysilylpropyl) maleate. ### Claim 69 (depends on 68) The process of claim 68 wherein the adhesion promoter is 1,3,5-tris(3-trimethoxysilylpropyl) isocyanurate. ### Claim 70 (depends on 68) The process of claim 68 wherein the adhesion promoter is bis(3-trimethoxysilylpropyl) fumarate. ### Claim 71 A process for forming self-bonding one-component RTV silicone rubber composition comprising (1) mixing (A) 100 parts by weight of a silanol end-stopped polymer of the formula, ##STR42## where s varies such that the viscosity of the polymer varies from 100 to 1,000,000 centipoise at 25.degree. C., with the reaction product of (B) from 0.1 to 10 parts by weight of a silyl ether cross-linking agent of the formula, ##STR43## where Q is a hydrolyzable radical, R is a C.sub.(1-13) monovalent organic radical, R.sup.1 is selected from hydrogen, halogen, and R, X, and Y are divalent radicals selected from --O--, --S-- and ##STR44## Z is a divalent C.sub.(1-13) organic radical selected from alkylene, cyclalkylene, arylene and a fused ring structure, b and c are equal to 0 or 1, R.sup.3 is selected from hydrogen and R, and d is a whole number having a value of 0 or 1, R.sup.5 is a C.sub.(1-13) monovalent organic radical; with (C) from 3 to 8 parts by weight of an adhesion promoter selected from the class consisting of silyl maleates, silyl fumarates, silyl succinates, silyl isocyanurates and mixtures thereof, and (2) allowing the composition to cure at room temperature. ### Claim 72 (depends on 71) The process of claim 71 wherein the silyl ether cross-linking agent, R.sup.5 is a C.sub.(4-12) alkyl radical. ### Claim 73 (depends on 72) The process of claim 72 where R.sup.5 is a dodecyl radical. ### Claim 74 (depends on 73) The process of claim 73 wherein the reaction product is formed by pre-reacting the cross-linking agent with the adhesion promoter at a temperature in the range of 40.degree. to 120.degree. C. ### Claim 75 (depends on 74) The process of claim 74 wherein the reaction product is formed by pre-reacting the cross-linking agent with the adhesion promoter for a period of time varying from 2 hours to 10 days. ### Claim 76 (depends on 75) The process of claim 75 wherein R is a mixture of methyl and 3,3,3-trifluoropropyl radicals. ### Claim 77 (depends on 76) The process of claim 76 wherein the adhesion promoter is bis(3-trimethoxysilylpropyl)maleate. ### Claim 78 (depends on 76) The process of claim 76 wherein the adhesion promoter is 1,3,5-tris(3-trimethoxysilylpropyl)isocyanurate. ### Claim 79 (depends on 76) The process of claim 76 wherein the adhesion promoter is bis(3-trimethoxysilylpropyl)fumarate. ### Claim 80 An article of manufacture comprising a laminate of a metallic substrate and a one-component self-bonding RTV silicone rubber composition, comprising, (1) a metallic substrate and (2) having thereover a layer of self-bonding one-component RTV silicone rubber composition having (A) 100 parts by weight of an organopolysiloxane consisting essentially of chemically combined units of the formula, ##STR45## and having terminal alkoxysiloxy units of the formula, ##STR46## where R is a C.sub.(1-13) monovalent organic radical, R.sup.1 is selected from hydrogen, halogen and R, R.sup.2 is a C.sub.(1-8) alkyl radical, X and Y are divalent radicals selected from --O--, --S-- and ##STR47## Z is a divalent C.sub.(1-13) organic radical selected from alkylene, cycloalkylene, arylene and fused ring structure, b and c are equal to 0 or 1, R.sup.3 is selected from hydrogen and R, e is a whole number having a value of 0 or 1, g is equal to 1 or 2, and the sum of e+g is equal to 1 or 2; (B) from 3 to 8 parts by weight of an adhesion promoter selected from the class consisting of silyl maleates, silyl fumarates, silyl succinates, silyl isocyanurates and mixtures thereof. ### Claim 81 (depends on 80) The laminate of claim 80 wherein there is further present from 0.01 to 10 parts by weight of a curing promoter which is a metal salt of carboxylic acid. ### Claim 82 (depends on 81) A laminate of claim 81 wherein R is selected from a mixture of methyl and 3,3,3-trifluoropropyl radicals. ### Claim 83 (depends on 82) The laminate of claim 82 wherein the adhesion promoter is bis(3-trimethoxysilylpropyl)maleate. ### Claim 84 (depends on 82) The laminate of claim 82 wherein the adhesion promoter is 1,3,5-tris(3-trimethoxysilylpropyl)isocyanurate. ### Claim 85 (depends on 82) The laminate of claim 82 wherein the adhesion promoter is bis(3-trimethoxysilylpropyl)fumarate. ### Claim 86 A laminate of a substrate and a silicone rubber composition comprising (1) a metallic substrate and (2) a layer over said substrate of a self-bonding one-component RTV silicone rubber composition having (A) 100 parts by weight of a silanol end-stopped polymer of the formula. ##STR48## where s varies such that the viscosity of the polymer varies from 100 to 1,000,000 centipoise at 25.degree. C., with the reaction product of (B) from 0.1 to 10 parts by weight of a silyl ether cross-linking agent of the formula, ##STR49## where Q is a hydrolyzable radical, R is a C.sub.(1-13) monovalent organic radical, R.sup.1 is selected from hydrogen, halogen, and R, R.sup.2 is a C.sub.(1-8) alkyl radical, X and Y are divalent radicals selected from --O--, --S-- and ##STR50## Z is a divalent C.sub.(1-13) organic radical selected from alkylene, cycloalkylene, arylene and a fused ring structure, b and c are equal to 0 or 1, R.sup.3 is selected from hydrogen and R, e is a whole number having a value of 0 or 1, g is equal to 1 or 2, and the sum of e+g is equal to 1 or 2; and (C) from 3 to 8 parts by weight of an adhesion promoter selected from the class consisting of silyl maleates, silyl fumarates, silyl succinates, silyl isocyanurates and mixtures thereof. ### Claim 87 (depends on 86) The laminate of claim 86 where it is further present from 0.01 to 10 parts by weight of a curing promoter which is a metal salt of a carboxylic acid. ### Claim 88 (depends on 87) The laminate of claim 87 where the reaction product is formed by pre-reacting the cross-linking agent with the adhesion promoter at a temperature in the range of 40.degree.-120.degree. C. ### Claim 89 (depends on 88) The laminate of claim 88 wherein the reaction product is formed by pre-reacting the cross-linking agent with the adhesion promoter for a period of time varying from 2 hours to 10 days. ### Claim 90 (depends on 89) The laminate of claim 89 wherein R is a mixture of methyl and 3,3,3-trifluoropropyl radicals. ### Claim 91 (depends on 90) The laminate of claim 90 wherein the adhesion promoter is bis(3-trimethoxysilylpropyl)maleate. ### Claim 92 (depends on 90) The process of claim 90 wherein the adhesion promoter is 1,3,5-tris(3-trimethoxysilylpropyl)isocyanurate. ### Claim 93 (depends on 90) The process of claim 90 wherein the adhesion promoter is bis(3-trimethoxysilylpropyl)fumarate. ### Claim 94 A laminate of a substrate and a silicone elastomer comprising (1) a metallic substrate and (2) applied over the substrate a layer of self-bonding one-component RTV silicone rubber composition having (A) 100 parts by weight of an organopolysiloxane consisting essentially of chemically combined units of the formula, ##STR51## and having terminal siloxy units of the formula, ##STR52## where R is a C.sub.(1-13) monovalent organic radical, R.sup.1 is selected from hydrogen, halogen and R, X, and Y are divalent radicals selected from --O--, --S-- and ##STR53## Z is a divalent C.sub.(1-13) organic radical selected from alkylene, cycloalkylene, arylene and a fused ring structure, b and c are equal to 0 or 1, R.sup.3 is selected from hydrogen and R, and d is a whole number having a value of 0 or 1, R.sup.5 is a C.sub.(1-13) monovalent organic radical, and (B) from 3 to 8 parts by weight of an adhesion promoter selected from the class consisting of silyl maleates, silyl fumarates, silyl succinates, silyl isocyanurates and mixtures thereof. ### Claim 95 (depends on 94) The composition of claim 94 wherein the base organopolysiloxane R.sup.5 is a C.sub.(4-12) alkyl radical. ### Claim 96 (depends on 95) The laminate of claim 95 wherein there is further present from 0.01 to 10 parts by weight of a curing promoter which is a metal salt of a carboxylic acid. ### Claim 97 (depends on 96) The laminate of claim 96 where R is selected from a mixture of methyl and 3,3,3-trifluoropropyl radicals. ### Claim 98 (depends on 96) The laminate of claim 96 where the adhesion promoter is bis(3-trimethoxysilylpropyl)maleate. ### Claim 99 (depends on 96) The laminate of claim 96 wherein the adhesion promoter is 1,3,5-tris(3-trimethoxysilylpropyl)isocyanurate. ### Claim 100 (depends on 96) The laminate of claim 96 wherein the adhesion promoter is bis(3-trimethoxysilylpropyl)fumarate. ### Claim 101 A laminate of a substrate and a silicone elastomer comprising (1) a metallic substrate and (2) applied over the substrate is layer of a self-bonding one-component RTV silicone rubber composition having (A) 100 parts by weight of a silanol end-stopped polymer of the formula, ##STR54## where s varies such that the viscosity of the polymer varies from 100 to 1,000,000 centipoise at 25.degree. C., with the reaction product of (B) from 0.1 to 10 parts by weight of a silyl ether cross-linking agent of the formula, ##STR55## where Q is a hydrolyzable radical, R is a C.sub.(1-13) monovalent organic radical, R.sup.1 is selected from hydrogen, halogen and R, X and Y are divalent radicals selected from --O--, --S-- and ##STR56## z is a divalent C.sub.(1-13) organic radical selected from alkylene, cycloalkylene, arylene and a fused ring structure, b and c are equal to 0 or 1, R.sup.3 is selected from hydrogen and R, and d is a whole number having a value of 0 or 1, R.sup.5 is a C.sub.(1-13) monovalent organic radical; and (C) from 3 to 8 parts by weight of an adhesion promoter selected from the class consisting of silyl maleates, silyl fumarates, silyl succinates, silyl isocyanurates and mixtures thereof. ### Claim 102 (depends on 101) The laminate of claim 101 wherein in the silyl ether cross-linking agent, R.sup.5 is a C.sub.(4-12) alkyl radical. ### Claim 103 (depends on 102) The laminate of claim 102 where R.sup.5 is a dodecyl radical. ### Claim 104 (depends on 101) The laminate of claim 101 wherein there is further present from 0.01 to 10 parts by weight of a curing promoter which is a metal salt of a carboxylic acid. ### Claim 105 (depends on 101) A laminate of claim 101 wherein the reaction product is formed by pre-reacting the cross-linking agent with adhesion promoter at a temperature range of 40.degree. to 120.degree. C. ### Claim 106 (depends on 105) The laminate of claim 105 wherein the reaction product is formed by pre-reacting the cross-linking agent with adhesion promoter for a period of time varying from 2 hours to 10 days. ### Claim 107 (depends on 102) The laminate of claim 102 where R is a mixture of methyl and 3,3,3-trifluoropropyl radicals. ### Claim 108 (depends on 102) The laminate of claim 102 where the adhesion promoter is bis(3-trimethoxysilylpropyl)maleate. ### Claim 109 (depends on 102) The laminate of claim 102 wherein the adhesion promoter is 1,3,5-tris(3-trimethoxysilylpropyl)isocyanurate. ### Claim 110 (depends on 102) The laminate of claim 102 wherein the adhesion promoter is bis(3-trimethoxysilylpropyl)fumarate.