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US4483972A Expired / Lapsed US ⏱️ 0.0 years remaining

Integrated cross-linkers and amine functional siloxane scavengers for RTV silicone rubber compositions

Assignee: General Electric Co
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Filing: 1983-02-01
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Granted: 1984-11-20
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Expires: 2003-02-01
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Abstract

Abstract The present invention relates to an alkoxy-functional one-component RTV silicone rubber composition having therein novel scavenger compounds. The novel scavenger compounds comprise multi-amine functional silanes and amine functional siloxanes which can be either pure scavengers or integrated cross-linker, scavengers.

Inventors

  • 👤 Tyrone D. Mitchell

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-30 14:35
CPC Classifications
C; C08; C08L; C08L83/00; C08L83/04; C08L83/08; C08G; C08G77/00; C08G77/48; C08G77/54; C08G77/04; C08G77/14; C08G77/16; C08G77/18; C08G77/20; C08G77/22; C08G77/26; C08G77/28; C08G77/42; C08G77/46; Y; Y10; Y10S; Y10S528/00; Y10S528/901

Claims Analysis

Total Claims: 35
Claim 1
Independent Claim 260 words
A shelf-stable, fast-curing one-component RTV silicone rubber composition comprising, (A) an organopolysiloxane polymer having a viscosity varying in the range of 100 to 1,000,000 centipoise at 25° C. where the organo groups are monovalent hydrocarbon radicals, and wherein in said polymer, the terminal silicon atoms in the polymer chain have bonded to them at least one alkoxy group; (B) an effective amount of a condensation catalyst; and (C) an effective amount of a scavenging compound of the formula, ##EQU1## where R 1 and R 2 are individually selected from C 1-13 monovalent hydrocarbon radicals and A is a radical selected from the group consisting of simple amine radicals of the formula, ##STR18## where R 10 and R 11 are individually selected from hydrogen C 1-8 monovalent hydrocarbon radicals, and multi-amine functional radicals of the formula, ##STR19## where R 3 is selected from the group consisting of hydrogen, C 1-8 monovalent hydrocarbon radicals, and a radical of the formula ##STR20## wherein R 8 and R 9 are individually selected from the group consisting of hydrogen and C 1-8 monovalent hydrocarbon radicals and R 7 is a C 2-8 divalent hydrocarbon radical; R 4 is a C 2-8 divalent hydrocarbon radical, R 5 and R 6 are individually selected from the group consisting of hydrogen and C 1-8 monovalent hydrocarbon radicals; x varies in the range of 0.00 to 2.50; y varies in the range of 0.00 to 2.50; and w varies in the range of 0.05 to 1.5; and the sum of x+y+w varies in the range of 2.10 to 3.00.
Claim 2
Dependent Claim 260 words
A shelf-stable, fast-curing one-component RTV silicone rubber composition comprising, (A) an organopolysiloxane polymer having a viscosity varying in the range of 100 to 1,000,000 centipoise at 25° C. where the organo groups are monovalent hydrocarbon radicals, and wherein in said polymer, the terminal silicon atoms in the polymer chain have bonded to them at least one alkoxy group; (B) an effective amount of a condensation catalyst; and (C) an effective amount of a scavenging compound of the formula, ##EQU1## where R 1 and R 2 are individually selected from C 1-13 monovalent hydrocarbon radicals and A is a radical selected from the group consisting of simple amine radicals of the formula, ##STR18## where R 10 and R 11 are individually selected from hydrogen C 1-8 monovalent hydrocarbon radicals, and multi-amine functional radicals of the formula, ##STR19## where R 3 is selected from the group consisting of hydrogen, C 1-8 monovalent hydrocarbon radicals, and a radical of the formula ##STR20## wherein R 8 and R 9 are individually selected from the group consisting of hydrogen and C 1-8 monovalent hydrocarbon radicals and R 7 is a C 2-8 divalent hydrocarbon radical; R 4 is a C 2-8 divalent hydrocarbon radical, R 5 and R 6 are individually selected from the group consisting of hydrogen and C 1-8 monovalent hydrocarbon radicals; x varies in the range of 0.00 to 2.50; y varies in the range of 0.00 to 2.50; and w varies in the range of 0.05 to 1.5; and the sum of x+y+w varies in the range of 2.10 to 3.00.
Claim 3
Dependent Claim 14 words
The composition of claim 1 wherein the condensation catalyst is a tin condensation catalyst.
Claim 4
Dependent Claim 44 words
The composition of claim 2 further comprising having an effective amount of cross-linking silane of the formula, ##STR21## where R 1 and R 2 are individually selected from C 1-13 monovalent hydrocarbon radicals and b is a whole number equal to 0 or 1.
Claim 5
Dependent Claim 26 words
The composition of claim 3 further comprising an effective amount of a cure accelerator selected from the group consisting of substituted guanidines, amines and mixtures thereof.
Claim 6
Dependent Claim 132 words
The composition of claim 4 further comprising a polyalkoxy-terminated organopolysiloxane polymer of the formula, ##STR22## where R, R 1 , R 2 are each individually selected from C 1-13 monovalent hydrocarbon radicals; b is a whole number equal to 0 or 1; e is a whole number which equals to 0 or 1, inclusive; n is an integer having a value of from about 50 to 2,500, inclusive; and X is a hydrolyzable leaving group selected from the class consisting of amido, cyclic amido, silazanyl, carbamato, enoxy, imidato, isocyanato, oximato, thioisocyanato, ureido radicals, and radicals selected from the class consisting of simple amine radicals of the formula, ##STR23## where R 10 , R 11 are individually selected from hydrogen, C 1-8 monovalent hydrocarbon radicals, and multi-amine functional radicals of the formula, ##STR24##
Claim 7
Dependent Claim 83 words
where R 3 is selected from the class consisting of hydrogen, C 1-8 monovalent hydrocarbon radicals, and a radical of the formula, ##STR25## wherein R 8 , R 9 are individually selected from the class consisting of hydrogen and C 1-8 monovalent hydrocarbon radicals and R 7 is a C 2-8 divalent hydrocarbon radical; R 5 and R 6 are individually selected from the class consisting of hydrogen and C 1-8 monovalent hydrocarbon radicals, R 4 is a C 2-8 divalent hydrocarbon radical.
Claim 8
Dependent Claim 83 words
where R 3 is selected from the class consisting of hydrogen, C 1-8 monovalent hydrocarbon radicals, and a radical of the formula, ##STR25## wherein R 8 , R 9 are individually selected from the class consisting of hydrogen and C 1-8 monovalent hydrocarbon radicals and R 7 is a C 2-8 divalent hydrocarbon radical; R 5 and R 6 are individually selected from the class consisting of hydrogen and C 1-8 monovalent hydrocarbon radicals, R 4 is a C 2-8 divalent hydrocarbon radical.
Claim 9
Dependent Claim 38 words
The composition of claim 5 wherein the cross-linking silane is methyltrimethoxysilane, the condensation catalyst is selected from the class consisting of dibutyltindiacetate and dibutyltindilaurate, and the curing accelerator is selected from the class consisting of di-n-hexylamine and di-n-butylamine.
Claim 10
Dependent Claim 33 words
The composition of claim 5 wherein the condensation catalyst is selected from the class consisting of dibutyltindiacetate and dibutyltindilaurate and the cure accelerator is selected from the class consisting of di-n-hexylamine and di-n-butylamine.
Claim 11
Dependent Claim 29 words
The composition of claim 5 wherein R, R 1 and R 2 are methyl and the tin condensation catalyst is selected from the class consisting of dibutyltindiacetate and dibutyltindilaurate.
Claim 12
Dependent Claim 246 words
A shelf-stable, fast-curing one-component RTV silicone rubber composition, comprising, (A) a silanol-terminated diorganopolysiloxane polymer having a viscosity in the range of 100 to 1,000,000 centipoise at 25° C. where the organo groups are monovalent hydrocarbon radicals; (B) an integrated cross-linker, scavenger compound of the formula, ##STR26## where R 1 and R 2 are individually selected from C 1-13 monovalent hydrocarbon radicals and A is a radical selected from the group consisting of simple amine radicals of the formula, ##STR27## where R 10 and R 11 are individually selected from hydrogen, C 1-8 monovalent hydrocarbon radicals, and multi-amine functional radicals of the formula, ##STR28## where R 3 is selected from the group consisting of hydrogen, C 1-8 monovalent hydrocarbon radicals, and a radical of the formula ##STR29## wherein R 8 and R 9 are individually selected from the group consisting of hydrogen and C 1-8 monovalent hydrocarbon radicals and R 7 is a C 2-8 divalent hydrocarbon radical, R 4 is a C 2-8 divalent hydrocarbon radical, R 5 and R 6 are individually selected from the group consisting of hydrogen and C 1-8 monovalent hydrocarbon radicals; m varies in the range of 0.15 to 2.50; n varies in the range of 0.1 to 1.9; an o varies in the range of 0.05 to 2.00; and the sum of m+n+o varies in the range of 2.10 to 3.00, which forms with the silanol-terminated polymer, an alkoxy terminated polymer; and (C) an effective amount of a condensation catalyst.
Claim 13
Dependent Claim 246 words
A shelf-stable, fast-curing one-component RTV silicone rubber composition, comprising, (A) a silanol-terminated diorganopolysiloxane polymer having a viscosity in the range of 100 to 1,000,000 centipoise at 25° C. where the organo groups are monovalent hydrocarbon radicals; (B) an integrated cross-linker, scavenger compound of the formula, ##STR26## where R 1 and R 2 are individually selected from C 1-13 monovalent hydrocarbon radicals and A is a radical selected from the group consisting of simple amine radicals of the formula, ##STR27## where R 10 and R 11 are individually selected from hydrogen, C 1-8 monovalent hydrocarbon radicals, and multi-amine functional radicals of the formula, ##STR28## where R 3 is selected from the group consisting of hydrogen, C 1-8 monovalent hydrocarbon radicals, and a radical of the formula ##STR29## wherein R 8 and R 9 are individually selected from the group consisting of hydrogen and C 1-8 monovalent hydrocarbon radicals and R 7 is a C 2-8 divalent hydrocarbon radical, R 4 is a C 2-8 divalent hydrocarbon radical, R 5 and R 6 are individually selected from the group consisting of hydrogen and C 1-8 monovalent hydrocarbon radicals; m varies in the range of 0.15 to 2.50; n varies in the range of 0.1 to 1.9; an o varies in the range of 0.05 to 2.00; and the sum of m+n+o varies in the range of 2.10 to 3.00, which forms with the silanol-terminated polymer, an alkoxy terminated polymer; and (C) an effective amount of a condensation catalyst.
Claim 14
Dependent Claim 38 words
The composition of claim 9 wherein the silanol-terminated diorganopolysiloxane polymer has the formula, ##STR30## wherein each R is individually selected from C 1-13 monovalent hydrocarbon radicals and n is a whole number that varies from 50 to 2,500.
Claim 15
Dependent Claim 81 words
The composition of claim 9 wherein the alkoxy-terminated polymer that is formed has the formula, ##STR31## where R, R 1 and R 2 are individually selected from C 1-13 monovalent hydrocarbon radicals; s is a whole number equal to 0 or 1; n is an integer that varies from 50 to 2,500, inclusive; t is a whole number equal to 1 or 2, inclusive; and the sum of s+t is equal to 1 to 2; and A is as previously defined.
Claim 16
Dependent Claim 14 words
The composition of claim 9 wherein the condensation catalyst is a tin condensation catalyst.
Claim 17
Dependent Claim 45 words
The composition of claim 12 further comprising having an effective amount of a cross-linking silane of the formula, ##STR32## where R 1 and R 2 are individually selected from C 1-13 monovalent hydrocarbon radicals; and b is a whole number equal to 0 or 1.
Claim 18
Dependent Claim 27 words
The composition of claim 13 further comprising adding an effective amount of a cure accelerator selected from the group consisting of substituted guanidines, amines and mixtures thereof.
Claim 19
Dependent Claim 227 words
The composition of claim 14 further comprising having therein a polyalkoxy-terminated organopolysiloxane polymer of the formula, ##STR33## where R, R 1 , R 2 are individually selected from C 1-13 monovalent hydrocarbon radicals; b+e are whole numbers equal to 0 or 1; e is a whole number which equals to 0 or 1, inclusive; and the sum of b+e is equal to 0 or 1, inclusive; n is an integer having a value of from about 50 to 2,500, inclusive; and X is a hydrolyzable leaving group selected from the class consisting of amido, cyclic aido, silazanyl, carbamato, enoxy, imidato, isocyanato, oximato, thioisocyanato, ureido radicals, and radicals selected from the class consisting of simple amine radicals of the formula, ##STR34## where R 10 , R 11 are individually selected from hydrogen, C 1-8 monovalent hydrocarbon radicals, and multi-amine functional radicals of the formula, ##STR35## where R 3 is selected from the class consisting of hydrogen, C 1-8 monovalent hydrocarbon radicals, and a radical of the formula, ##STR36## wherein R 8 , R 9 are individually selected from the class consisting of hydrogen and C 1-8 monovalent hydrocarbon radicals and R 7 is a C 2-8 divalent hydrocarbon radical; R 5 and R 6 are individually selected from the class consisting of hydrogen and C 1-8 monovalent hydrocarbon radicals, R 4 is a C 2-8 divalent hydrocarbon radical.
Claim 20
Dependent Claim 38 words
The composition of claim 15 wherein the cross-linking silane is methyltrimethoxy silane, the condensation catalyst is selected from the class consisting of dibutyltindiacetate and dibutyltindilaurate and a curing accelerator selected from the class consisting of di-n-hexylamine and di-n-butylamine.
Claim 21
Dependent Claim 33 words
The composition of claim 15 wherein the condensation catalyst is selected from the class consisting of dibutyltindiacetate and dibutyltindilaurate and the cure accelerator is selected from the class consisting of di-n-hexylamine and di-n-butylamine.
Claim 22
Dependent Claim 30 words
The composition of claim 15 wherein R, R 1 , and R 2 are methyl and the tin condensation catalyst is selected from the class consisting of dibutyltindiacetate and dibutyltindilaurate.
Claim 23
Dependent Claim 262 words
A process for producing a shelf-stable, fast-curing one-component RTV silicone rubber composition comprising, mixing anhydrously, (A) an organopolysiloxane polymer having a viscosity varying in the range of 100 to 1,000,000 centipoise at 25° C. where the organo groups are monovalent hydrocarbon radicals, and wherein the terminal silicon atoms of said polymer have bonded to them at least one alkoxy group; (B) an effective amount of a condensation catalyst; and (C) an effective amount of a scavenging compound of the formula ##STR37## where R 1 and R 2 are individually selected from C 1-13 monovalent hydrocarbon radicals and A is a radical selected from the group consisting of simple amine radicals of the formula, ##STR38## where R 10 and R 11 are individually selected from hydrogen, C 1-8 monovalent hydrocarbon radicals, and multi-amine functional radicals of the formula, ##STR39## where R 3 is selected from the group consisting of hydrogen, C 1-8 monovalent hydrocarbon radicals, and a radical of the formula ##STR40## wherein R 8 and R 9 are individually selected from the group consisting of hydrogen and C 1-8 monovalent hydrocarbon radicals and R 7 is a C 2-8 divalent hydrocarbon radical, R 4 is a C 2-8 divalent hydrocarbon radical, R 5 and R 6 are individually selected from the group consisting of hydrogen and C 1-8 monovalent hydrocarbon radicals; x varies in the range of 0.00 to 2.50; y varies in the range of 0.00 to 2.50; and w varies in the range of 0.05 to 1.5; and the sum of x+y+w varies in the range of 2.10 to 3.00.
Claim 24
Dependent Claim 262 words
A process for producing a shelf-stable, fast-curing one-component RTV silicone rubber composition comprising, mixing anhydrously, (A) an organopolysiloxane polymer having a viscosity varying in the range of 100 to 1,000,000 centipoise at 25° C. where the organo groups are monovalent hydrocarbon radicals, and wherein the terminal silicon atoms of said polymer have bonded to them at least one alkoxy group; (B) an effective amount of a condensation catalyst; and (C) an effective amount of a scavenging compound of the formula ##STR37## where R 1 and R 2 are individually selected from C 1-13 monovalent hydrocarbon radicals and A is a radical selected from the group consisting of simple amine radicals of the formula, ##STR38## where R 10 and R 11 are individually selected from hydrogen, C 1-8 monovalent hydrocarbon radicals, and multi-amine functional radicals of the formula, ##STR39## where R 3 is selected from the group consisting of hydrogen, C 1-8 monovalent hydrocarbon radicals, and a radical of the formula ##STR40## wherein R 8 and R 9 are individually selected from the group consisting of hydrogen and C 1-8 monovalent hydrocarbon radicals and R 7 is a C 2-8 divalent hydrocarbon radical, R 4 is a C 2-8 divalent hydrocarbon radical, R 5 and R 6 are individually selected from the group consisting of hydrogen and C 1-8 monovalent hydrocarbon radicals; x varies in the range of 0.00 to 2.50; y varies in the range of 0.00 to 2.50; and w varies in the range of 0.05 to 1.5; and the sum of x+y+w varies in the range of 2.10 to 3.00.
Claim 25
Dependent Claim 249 words
A process for forming a shelf-stable, fast-curing one-component RTV silicone rubber composition, comprising, mixing in a substantially anhydrous manner, (A) a silanol-terminated diorganopolysiloxane polymer having a viscosity in the range of 100 to 1,000,000 centipoise at 25° C. where the organo groups are monovalent hydrocarbon radicals; (B) an effective amount of a scavenging compound of the formula, ##STR41## where R 1 and R 2 are individually selected from C 1-13 monovalent hydrocarbon radicals and A is a radical selected from the group consisting of a simple amine radical of the formula, ##STR42## where R 10 and R 11 are each individually selected from hydrogen, C 1-8 monovalent hydrocarbon radicals, and multi-amine functional radicals of the formula, ##STR43## where R 3 is selected from the group consisting of hydrogen, C 1-8 monovalent hydrocarbon radicals, and a radical of the formula ##STR44## wherein R 8 and R 9 are individually selected from the group consisting of hydrogen and C 1-8 monovalent hydrocarbon radicals and R 7 is a C 2-8 divalent hydrocarbon radical, R 4 is a C 2-8 divalent hydrocarbon radical, R 5 and R 6 are individually selected from the group consisting of hydrogen and C 1-8 monovalent hydrocarbon radicals; m varies in the range of 0.15 to 2.50; n varies in the range of 0.1 to 1.9; and o varies in the range of 0.05 to 2.00; and the sum of m+n+o varies in the range of 2.10 to 3.00. (C) an effective amount of a condensation catalyst.
Claim 26
Dependent Claim 249 words
A process for forming a shelf-stable, fast-curing one-component RTV silicone rubber composition, comprising, mixing in a substantially anhydrous manner, (A) a silanol-terminated diorganopolysiloxane polymer having a viscosity in the range of 100 to 1,000,000 centipoise at 25° C. where the organo groups are monovalent hydrocarbon radicals; (B) an effective amount of a scavenging compound of the formula, ##STR41## where R 1 and R 2 are individually selected from C 1-13 monovalent hydrocarbon radicals and A is a radical selected from the group consisting of a simple amine radical of the formula, ##STR42## where R 10 and R 11 are each individually selected from hydrogen, C 1-8 monovalent hydrocarbon radicals, and multi-amine functional radicals of the formula, ##STR43## where R 3 is selected from the group consisting of hydrogen, C 1-8 monovalent hydrocarbon radicals, and a radical of the formula ##STR44## wherein R 8 and R 9 are individually selected from the group consisting of hydrogen and C 1-8 monovalent hydrocarbon radicals and R 7 is a C 2-8 divalent hydrocarbon radical, R 4 is a C 2-8 divalent hydrocarbon radical, R 5 and R 6 are individually selected from the group consisting of hydrogen and C 1-8 monovalent hydrocarbon radicals; m varies in the range of 0.15 to 2.50; n varies in the range of 0.1 to 1.9; and o varies in the range of 0.05 to 2.00; and the sum of m+n+o varies in the range of 2.10 to 3.00. (C) an effective amount of a condensation catalyst.
Claim 27
Dependent Claim 39 words
The process of claim 20 wherein the silanol terminated diorganopolysiloxane polymer has the formula, ##STR45## wherein each R is individually selected from C 1-13 monovalent hydrocarbon radicals and n is a whole number that varies from 50 to 2,500.
Claim 28
Dependent Claim 71 words
The process of claim 20 wherein the alkoxy-terminated polymer that is formed has the formula, ##STR46## where R, R 1 , and R 2 are individually selected from C 1-13 monovalent hydrocarbon radicals; s is a whole number equal to 0 or 1; t is a whole number equal to 1 or 2, inclusive; and the sum of s+t is equal to 1 to 2; and A is as previously defined.
Claim 29
Dependent Claim 14 words
The process of claim 20 wherein the condensation catalyst is a tin condensation catalyst.
Claim 30
Dependent Claim 48 words
The process of claim 23 further comprising adding an effective amount of a cross-linking silane of the formula, ##STR47## where R 1 and R 2 are each individually selected from C 1-13 monovalent hydrocarbon radicals and b is a whole number that is equal to 0 or 1.
Claim 31
Dependent Claim 26 words
The process of claim 24 further comprising an effective amount of a cure accelerator selected from the group consisting of substituted guanidines, amines and mixtures thereof.
Claim 32
Dependent Claim 214 words
The process of claim 25 further comprising polyalkoxy-terminated organopolysiloxane polymer of the formula, ##STR48## where R, R 1 , R 2 are individually selected from C 1-13 monovalent hydrocarbon radicals; b is a whole number equal to 0 or 1; e is a whole number which equals 0 or 1, inclusive; the sum of b+e is equal to 0 or 1, inclusive; n is an integer having a value of from about 50 to 2,500, inclusive; and X is a radical selected from the class consisting of amido, cyclic amido, silazanyl, carbamato, enoxy, imidato, isocyanato, oximato, thioisocyanato, ureido radicals, and simple amine radicals of the formula, ##STR49## where R 10 , R 11 are individually selected from hydrogen, C 1-8 monovalent hydrocarbon radicals, and multi-amine functional radicals of the formula, ##STR50## where R 3 is selected from the class consisting of hydrogen, C 1-8 monovalent hydrocarbon radicals, and a radical of the formula, ##STR51## wherein R 8 , R 9 are individually selected from the class consisting of hydrogen and C 1-8 monovalent hydrocarbon radicals and R 7 is a C 2-8 divalent hydrocarbon radical; R 5 and R 6 are individually selected from the class consisting of hydrogen and C 1-8 monovalent hydrocarbon radicals, R 4 is a C 2-8 divalent hydrocarbon radical.
Claim 33
Dependent Claim 38 words
The process of claim 26 wherein the cross-linking silane is methyltrimethoxysilane, the condensation catalyst is selected from the class consisting of dibutyltindiacetate and dibutyltindilaurate, and the curing accelerator is selected from the class consisting of di-n-hexylamine and di-n-butylamine.
Claim 34
Dependent Claim 32 words
The process of claim 26, wherein the condensation catalyst is selected from the class consisting of dibutyltindiacetate and dibutyltindilaurate and the accelerator is selected from the class consisting of di-n-hexylamine and di-n-butylamine.
Claim 35
Dependent Claim 30 words
The process of claim 26 wherein R, R 1 , and R 2 are methyl and the tin condensation catalyst is selected from the class consisting of dibutyltindiacetate and dibutyltindilaurate.

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