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US4395526A
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One package, stable, moisture curable, polyalkoxy-terminated organopolysiloxane compositions and method for making
Assignee: General Electric Co
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Filing: 1981-06-26
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Granted: 1983-07-26
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Expires: 2001-06-26
Abstract
Abstract Stable, substantially acid-free, one package moisture curable polyalkoxy-terminated organopolysiloxane compositions are provided having a condensation catalyst such as a tin compound. A method for making the aforesaid moisture curable organopolysiloxane compositions, is also provided.
Inventors
- 👤 Mary A. White
- 👤 Melvin D. Beers
- 👤 Gary M. Lucas
- 👤 Robert A. Smith
- 👤 Roger T. Swiger
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 11:24
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/29; C08K5/31; C08G; C08G77/00; C08G77/04; C08G77/14; C08G77/18; C08L; C08L83/00; C08L83/04; C08G77/20; C08G77/22; C08G77/26; C08G77/28; C08G77/60; Y; Y10; Y10S; Y10S528/00; Y10S528/901
Claims Analysis
Total Claims: 44
Claim 1
Independent Claim
201 words
A stable, one-package, substantially anhydrous and substantially acid-free, room temperature vulcanizable organopolysiloxane composition stable under ambient conditions in the substantial absence of moisture over an extended period of time and convertible to a tack-free elastomer comprising: (1) an organopolysiloxane wherein the silicon atom at each polymer chain end is terminated with at least 2 alkoxy radicals; (2) an effective amount of a condensation catalyst; (3) a stabilizing amount of silane scavenger for hydroxy functional groups having the formula ##STR14## where R 1 is a C.sub.(1-8) aliphatic organic radical selected from the group consisting of alkyl, alkylether, alkylester, alkylketone, and alkylcyano radicals, or a C.sub.(7-13) aralkyl radical, R 2 is a C.sub.(1-13) monovalent substituted or unsubstituted hydrocarbon radical, X is a hydrolyzable leaving group selected from the group consisting of amido, amino, carbamato, enoxy, imidato, isocyanato, oximato, thioisocyanato and ureido radicals and, c is a whole number equal to 0 to 3 inclusive, f is an integer equal to 1 to 4 inclusive and the sum of c+f is equal to 1 to 4 inclusive; and where X is enoxy or amido, (4) an effective amount of a curing accelerator selected from the group consisting of substituted guanidines, amines and mixtures thereof.
Claim 2
Dependent Claim
201 words
A stable, one-package, substantially anhydrous and substantially acid-free, room temperature vulcanizable organopolysiloxane composition stable under ambient conditions in the substantial absence of moisture over an extended period of time and convertible to a tack-free elastomer comprising: (1) an organopolysiloxane wherein the silicon atom at each polymer chain end is terminated with at least 2 alkoxy radicals; (2) an effective amount of a condensation catalyst; (3) a stabilizing amount of silane scavenger for hydroxy functional groups having the formula ##STR14## where R 1 is a C.sub.(1-8) aliphatic organic radical selected from the group consisting of alkyl, alkylether, alkylester, alkylketone, and alkylcyano radicals, or a C.sub.(7-13) aralkyl radical, R 2 is a C.sub.(1-13) monovalent substituted or unsubstituted hydrocarbon radical, X is a hydrolyzable leaving group selected from the group consisting of amido, amino, carbamato, enoxy, imidato, isocyanato, oximato, thioisocyanato and ureido radicals and, c is a whole number equal to 0 to 3 inclusive, f is an integer equal to 1 to 4 inclusive and the sum of c+f is equal to 1 to 4 inclusive; and where X is enoxy or amido, (4) an effective amount of a curing accelerator selected from the group consisting of substituted guanidines, amines and mixtures thereof.
Claim 3
Dependent Claim
140 words
The composition of claim 1 wherein the silane has the formula ##STR15## where R 1 is a C.sub.(1-8) aliphatic organic radical selected from the group consisting of alkyl, alkylether, alkylester, alkylketone and alkylcyano radicals, or a C.sub.(7-13) aralkyl radical, R 2 is a C.sub.(1-13) monovalent substituted or unsubstituted hydrocarbon radical, X is a hydrolyzable leaving group selected from the group consisting of amido, amino, carbamato, enoxy, imidato, isocyanato, oximato, thioisocyanato and ureido radicals; and, a is an integer equal to 1 to 2 inclusive, b is a whole number equal to 0 to 1 inclusive, and the sum of b+a is equal to 1 to 2 inclusive and the silane is both the silane scavenger for hydroxy functional groups and a polyalkoxysilane cross-linking agent for terminating the silicon atom at each organopolysiloxane chain end with at least two alkoxy radicals.
Claim 4
Dependent Claim
195 words
A stable, one-package, substantially anhydrous and substantially acid-free, room temperature vulcanizable organopolysiloxane composition stable under ambient conditions in the substantial absence of moisture over an extended period of time and convertible to a tack-free elastomer comprising: (1) an organopolysiloxane wherein the silicon atom at each polymer chain end is terminated with at least 2 alkoxy radicals; (2) an effective amount of a condensation catalyst; (3) a stabilizing amount of silane scavenger for hydroxy functional groups having the formula ##STR16## where R 1 is a C.sub.(1-8) aliphatic organic radical selected from the group consisting of alkyl, alkylether, alkylester, alkylketone and alkylcyano radicals, or a C.sub.(7-13) aralkyl radical, R 2 is a C.sub.(1-13) monovalent substituted or unsubstituted hydrocarbon radical, X is a hydrolyzable leaving group selected from the group consisting of amido, amino, carbamato, enoxy, imidato, isocyanato, oximato, thioisocyanato and ureido radicals and, c is a whole number equal to 0 to 3 inclusive, f is an integer equal to 1 to 4 inclusive and the sum of c+f is equal to 1 to 4 inclusive; and (4) an effective amount of a curing accelerator selected from the group consisting of substituted guanidines, amines and mixtures thereof.
Claim 5
Dependent Claim
195 words
A stable, one-package, substantially anhydrous and substantially acid-free, room temperature vulcanizable organopolysiloxane composition stable under ambient conditions in the substantial absence of moisture over an extended period of time and convertible to a tack-free elastomer comprising: (1) an organopolysiloxane wherein the silicon atom at each polymer chain end is terminated with at least 2 alkoxy radicals; (2) an effective amount of a condensation catalyst; (3) a stabilizing amount of silane scavenger for hydroxy functional groups having the formula ##STR16## where R 1 is a C.sub.(1-8) aliphatic organic radical selected from the group consisting of alkyl, alkylether, alkylester, alkylketone and alkylcyano radicals, or a C.sub.(7-13) aralkyl radical, R 2 is a C.sub.(1-13) monovalent substituted or unsubstituted hydrocarbon radical, X is a hydrolyzable leaving group selected from the group consisting of amido, amino, carbamato, enoxy, imidato, isocyanato, oximato, thioisocyanato and ureido radicals and, c is a whole number equal to 0 to 3 inclusive, f is an integer equal to 1 to 4 inclusive and the sum of c+f is equal to 1 to 4 inclusive; and (4) an effective amount of a curing accelerator selected from the group consisting of substituted guanidines, amines and mixtures thereof.
Claim 6
Dependent Claim
142 words
A one-package, room temperature vulcanizable polyalkoxy-terminated organopolysiloxane composition in accordance with claim 1, where the polyalkoxy-terminated organopolysiloxane has the formula ##STR17## where R is a C.sub.(1-13) monovalent substituted or unsubstituted hydrocarbon radical, R 1 is a C.sub.(1-8) aliphatic organic radical selected from the group consisting of alkyl, alkylether, alkylester, alkylketone and alkylcyano radicals, or a C.sub.(7-13) aralkyl radical, R 2 is a C.sub.(1-13) monovalent substituted or unsubstituted hydrocarbon radical, X is a hydrolyzable leaving group selected from the group consisting of amido, amino, carbamato, enoxy, imidato, isocyanato, oximato, thioisocyanato and ureido radicals and, b is a whole number equal to 0 or 1, e is a whole number equal to 0 or 1 inclusive and the sum of b+e is equal to 0 or 1 inclusive, and n is an integer having a value of from about 50 to about 2500 inclusive.
Claim 7
Dependent Claim
71 words
A room temperature vulcanizable composition in accordance with claim 1 having an effective amount of a cross-linking silane of the formula ##STR18## where R 1 is a C.sub.(1-8) aliphatic organic radical selected from the group consisting of alkyl, alkylether, alkylester, alkylketone and alkylcyano radicals, or a C.sub.(7-13) aralkyl radical, R 2 is a C.sub.(1-13) monovalent substituted or unsubstituted hydrocarbon radical, and b is a whole number equal to 0 or 1.
Claim 8
Dependent Claim
16 words
A room temperature vulcanizable composition in accordance with claim 1, where the silane scavenger is methyldimethoxy(N-methylacetamido)silane.
Claim 9
Dependent Claim
19 words
A room temperature vulcanizable composition in accordance with claim 1, which contains a tin compound as the condensation catalyst.
Claim 10
Dependent Claim
29 words
A room temperature vulcanizable composition in accordance with claim 4, where R, R 1 and R 2 are methyl and which has a tin compound as a condensation catalyst.
Claim 11
Dependent Claim
30 words
A room temperature vulcanizable composition in accordance with claim 1, containing an effective amount of a curing accelerator selected from the group consisting of substituted guanidines, amines and mixtures thereof.
Claim 12
Dependent Claim
32 words
A stable, one-package, substantially anhydrous and substantially acid-free, room temperature vulcanizable composition comprising a polymethoxy-terminated polydimethylsiloxane, an effective amount of a tin containing condensation catalyst, and a stabilizing amount of a polymethoxydi-n-hexylaminosilane.
Claim 13
Dependent Claim
32 words
A stable, one-package, substantially anhydrous and substantially acid-free, room temperature vulcanizable composition comprising a polymethoxy-terminated polydimethylsiloxane, an effective amount of a tin containing condensation catalyst, and a stabilizing amount of a polymethoxydi-n-hexylaminosilane.
Claim 14
Dependent Claim
39 words
A stable, one-package, substantially anhydrous and substantially acid-free, room temperature vulcanizable composition comprising a polymethoxy-terminated polydimethylsiloxane, and effective amount of a tin containing condensation catalyst, an effective amount of trimethoxysilylpropyltetramethylguanidine curing accelerator and a stabilizing amount of a polymethoxyacetamidosilane.
Claim 15
Dependent Claim
39 words
A stable, one-package, substantially anhydrous and substantially acid-free, room temperature vulcanizable composition comprising a polymethoxy-terminated polydimethylsiloxane, and effective amount of a tin containing condensation catalyst, an effective amount of trimethoxysilylpropyltetramethylguanidine curing accelerator and a stabilizing amount of a polymethoxyacetamidosilane.
Claim 16
Dependent Claim
10 words
An RTV composition in accordance with claim 10 containing dibutyltindiacetate.
Claim 17
Dependent Claim
13 words
An RTV composition in accordance with claim 10 containing a polymethoxysilane cross-linking agent.
Claim 18
Dependent Claim
261 words
A stable and substantially acid-free, one-package room temperature vulcanizable polyalkoxy-terminated organopolysiloxane composition curable under ambient conditions to a tack-free elastomer over an extended period of time comprising on a weight basis, (i) 100 parts of a substantially silanol-free polyalkoxysiloxydiorganopolysiloxane of the formula ##STR19## (ii) 0 to 10 parts of a cross-linking polyalkoxysilane of the formula ##STR20## (iii) an effective amount of a condensation catalyst, and (iv) a stabilizing amount of a silane scavenger for hydroxy functional groups having the formula ##STR21## where R is a C.sub.(1-13) monovalent substituted or unsubstituted hydrocarbon radical, R 1 is a C.sub.(1-8) aliphatic organic radical selected from the group consisting of alkyl, alkylether, alkylester, alkylketone and alkylcyano radicals, or a C.sub.(7-13) aralkyl radical, R 2 is a C.sub.(1-13) monovalent substituted or unsubstituted hydrocarbon radical, X is a hydrolyzable leaving group selected from the group consisting of amido, amino, carbamato, enoxy, imidato, isocyanato, oximato, thioisocyanato and ureido radicals and, b is a whole number equal to 0 or 1, e is a whole number equal to 0 to 1 inclusive, and the sum of b+e is equal to 0 or 1 inclusive, and n is an integer having a value of from about 50 to about 2500 inclusive, c is a whole number equal to 0 to 3 inclusive, f is an integer equal to 1 to 4 inclusive and the sum of c+f is equal to 1 to 4 inclusive; and (v) where X is enoxy, 0.1 to 5 parts of a curing accelerator selected from the group consisting of substituted guanidines, amines and mixtures thereof.
Claim 19
Dependent Claim
261 words
A stable and substantially acid-free, one-package room temperature vulcanizable polyalkoxy-terminated organopolysiloxane composition curable under ambient conditions to a tack-free elastomer over an extended period of time comprising on a weight basis, (i) 100 parts of a substantially silanol-free polyalkoxysiloxydiorganopolysiloxane of the formula ##STR19## (ii) 0 to 10 parts of a cross-linking polyalkoxysilane of the formula ##STR20## (iii) an effective amount of a condensation catalyst, and (iv) a stabilizing amount of a silane scavenger for hydroxy functional groups having the formula ##STR21## where R is a C.sub.(1-13) monovalent substituted or unsubstituted hydrocarbon radical, R 1 is a C.sub.(1-8) aliphatic organic radical selected from the group consisting of alkyl, alkylether, alkylester, alkylketone and alkylcyano radicals, or a C.sub.(7-13) aralkyl radical, R 2 is a C.sub.(1-13) monovalent substituted or unsubstituted hydrocarbon radical, X is a hydrolyzable leaving group selected from the group consisting of amido, amino, carbamato, enoxy, imidato, isocyanato, oximato, thioisocyanato and ureido radicals and, b is a whole number equal to 0 or 1, e is a whole number equal to 0 to 1 inclusive, and the sum of b+e is equal to 0 or 1 inclusive, and n is an integer having a value of from about 50 to about 2500 inclusive, c is a whole number equal to 0 to 3 inclusive, f is an integer equal to 1 to 4 inclusive and the sum of c+f is equal to 1 to 4 inclusive; and (v) where X is enoxy, 0.1 to 5 parts of a curing accelerator selected from the group consisting of substituted guanidines, amines and mixtures thereof.
Claim 20
Dependent Claim
32 words
A room temperature vulcanizable polyalkoxy-terminated organopolysiloxane composition in accordance with claim 14 containing an effective amount of a curing accelerator selected from the group consisting of substituted guanidines, amines and mixtures thereof.
Claim 21
Dependent Claim
20 words
A one-package room temperature vulcanizable composition in accordance with claim 14, where R, R 1 and R 2 are methyl.
Claim 22
Dependent Claim
19 words
A one-package room temperature vulcanizable composition in accordance with claim 14, where the condensation catalyst is a tin compound.
Claim 23
Dependent Claim
80 words
A stable and substantially acid-free, one-package, room temperature vulcanizable composition comprising a polymethoxy-terminated polydimethylsiloxane, a polymethoxysilane, an effective amount of a curing accelerator selected from the group consisting of substituted guanidines, amines and mixtures thereof, an effective amount of a tin compound condensation catalyst, and a stabilizing amount of a silane scavenger for hydroxy functional groups having at least one hydrolyzable leaving group selected from the group consisting of amido, amino, carbamato, enoxy, imidato, isocyanato, oximato, thioisocyanato and ureido radicals.
Claim 24
Dependent Claim
80 words
A stable and substantially acid-free, one-package, room temperature vulcanizable composition comprising a polymethoxy-terminated polydimethylsiloxane, a polymethoxysilane, an effective amount of a curing accelerator selected from the group consisting of substituted guanidines, amines and mixtures thereof, an effective amount of a tin compound condensation catalyst, and a stabilizing amount of a silane scavenger for hydroxy functional groups having at least one hydrolyzable leaving group selected from the group consisting of amido, amino, carbamato, enoxy, imidato, isocyanato, oximato, thioisocyanato and ureido radicals.
Claim 25
Dependent Claim
16 words
A one-package room temperature vulcanizable composition in accordance with claim 18, where the polymethoxysilane is methyltrimethoxysilane.
Claim 26
Dependent Claim
14 words
A one-package RTV in accordance with claim 18, where the substituted quanidine is butyltetramethylguanidine.
Claim 27
Dependent Claim
15 words
A one-package RTV in accordance with claim 18, where the organic amine is a dialkylamine.
Claim 28
Dependent Claim
50 words
A substantially acid-free room temperature vulcanizable composition comprising methyldimethoxysiloxy terminated polydimethylsiloxane, a reinforcing amount of octamethylcyclotetrasiloxane treated silica filler, an effective amount of dibutyltindiacetate condensation catalyst, a cure accelerating amount of trimethoxysilylpropyltetramethylguanidine and an excess of up to 3% by weight, based on the weight of the polydimethylsiloxane of methyldimethoxy-(N-methylacetamido)silane.
Claim 29
Dependent Claim
50 words
A substantially acid-free room temperature vulcanizable composition comprising methyldimethoxysiloxy terminated polydimethylsiloxane, a reinforcing amount of octamethylcyclotetrasiloxane treated silica filler, an effective amount of dibutyltindiacetate condensation catalyst, a cure accelerating amount of trimethoxysilylpropyltetramethylguanidine and an excess of up to 3% by weight, based on the weight of the polydimethylsiloxane of methyldimethoxy-(N-methylacetamido)silane.
Claim 30
Dependent Claim
38 words
A one-package, stable room temperature vulcanizable composition in accordance with claim 22, having as the silane in place of the acetamido an excess of up to 3% by weight, based on the weight of the polydimethylsiloxane of methyldimethoxyisopropenoxysilane.
Claim 31
Dependent Claim
23 words
A room temperature vulcanizable composition in accordance with claim 22 having up to 10 parts of methyltrimethoxysilane per 100 parts of the polydimethylsiloxane.
Claim 32
Dependent Claim
22 words
A room temperature vulcanizable composition in accordance with claim 22 having an effective amount of di-n-hexylamine curing accelerator in place of trimethoxysilylpropyltetramethylguanidine.
Claim 33
Dependent Claim
218 words
In the method of making a substantially acid-free room temperature vulcanizable organopolysiloxane composition under substantially anhydrous conditions utilizing an effective amount of a condensation catalyst with an organopolysiloxane wherein the silicon atom at each polymer chain end is terminated with at least two alkoxy radicals, the improvement which comprises adding to said polyalkoxy-terminated organopolysiloxane (1) a stabilizing amount of a silane scavenger for hydroxy functional groups of the formula ##STR22## where R 1 is a C.sub.(1-8) aliphatic organic radical selected from the group consisting of alkyl, alkylether, alkylester, alkylketone and alkylcyano radicals, or a C.sub.(7-13) aralkyl radical, R 2 is a C.sub.(1-13) monovalent substituted or unsubstituted hydrocarbon radical, X is a hydrolyzable leaving group selected from the group consisting of amido, amino, carbamato, enoxy, imidato, isocyanato, oximato, thioisocyanato and ureido radicals and, c is a whole number equal to 0 to 3 inclusive, f is an integer equal to 1 to 4 inclusive, and the sum of c+f is equal to 1 to 4 inclusive, and (2) an effective amount of a condensation catalyst, whereby improved stability is achieved in the resulting room temperature vulcanizable organopolysiloxane composition, and (3) where X is enoxy, adding before or with the scavenger an effective amount of a curing accelerator selected from the group consisting of substituted guanidines, amines and mixtures thereof.
Claim 34
Dependent Claim
218 words
In the method of making a substantially acid-free room temperature vulcanizable organopolysiloxane composition under substantially anhydrous conditions utilizing an effective amount of a condensation catalyst with an organopolysiloxane wherein the silicon atom at each polymer chain end is terminated with at least two alkoxy radicals, the improvement which comprises adding to said polyalkoxy-terminated organopolysiloxane (1) a stabilizing amount of a silane scavenger for hydroxy functional groups of the formula ##STR22## where R 1 is a C.sub.(1-8) aliphatic organic radical selected from the group consisting of alkyl, alkylether, alkylester, alkylketone and alkylcyano radicals, or a C.sub.(7-13) aralkyl radical, R 2 is a C.sub.(1-13) monovalent substituted or unsubstituted hydrocarbon radical, X is a hydrolyzable leaving group selected from the group consisting of amido, amino, carbamato, enoxy, imidato, isocyanato, oximato, thioisocyanato and ureido radicals and, c is a whole number equal to 0 to 3 inclusive, f is an integer equal to 1 to 4 inclusive, and the sum of c+f is equal to 1 to 4 inclusive, and (2) an effective amount of a condensation catalyst, whereby improved stability is achieved in the resulting room temperature vulcanizable organopolysiloxane composition, and (3) where X is enoxy, adding before or with the scavenger an effective amount of a curing accelerator selected from the group consisting of substituted guanidines, amines and mixtures thereof.
Claim 35
Dependent Claim
13 words
A method in accordance with claim 26, where th silane scavenger is methyldimethoxy-(N-methylacetamido)silane.
Claim 36
Dependent Claim
13 words
A method in accordance with claim 26, where the silane scavenger is methyldimethoxyisopropenoxysilane.
Claim 37
Dependent Claim
19 words
A method in accordance with claim 26, utilizing a stabilizing amount of methyltriisopropenoxysilane and an effective amount of methyltrimethoxysilane.
Claim 38
Dependent Claim
17 words
A method in accordance with claim 26, using an effective amount of dibutyltindiacetate as the condensation catalyst.
Claim 39
Dependent Claim
31 words
A room temperature vulcanizable composition in accordance with claim 5, where the cross-linking silane is methyltrimethoxysilane, the condensation catalyst is dibutyltindiacetate or dibutyltindilaurate, and the curing accelerator is di-n-hexylamine or di-n-butylamine.
Claim 40
Dependent Claim
32 words
A one-package room temperature vulcanizable composition in accordance with claim 17, where the tin compound is dibutyltindiacetate or dibutyltindilaurate, the cross-linking silane is methyltrimethoxysilane and the curing accelerator is di-n-hexylamine or di-n-butylamine.
Claim 41
Dependent Claim
27 words
A one-package room temperature vulcanizable composition in accordance with claim 19, where the tin compound is dibutyltindiacetate or dibutyltindilaurate, and the curing accelerator is di-n-hexylamine or di-n-butylamine.
Claim 42
Dependent Claim
25 words
A method in accordance with claim 30, using an effective amount of methyltrimethoxysilane, and an effective amount of di-n-hexylamine or di-n-butylamine as the curing accelerator.
Claim 43
Dependent Claim
17 words
A method in accordance with claim 26, using an effective amount of dibutyltindilaurate as the condensation catalyst.
Claim 44
Dependent Claim
25 words
A method in accordance with claim 35, using an effective amount of methyltrimethoxysilane, and an effective amount of di-n-hexylamine or di-n-butylamine as the curing accelerator.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-07-25 | 1987-01-24 | 1987-07-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-07-25 | 1991-01-24 | 1991-07-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-07-25 | 1995-01-24 | 1995-07-26 | $7700.00 | Window Closed / Lapsed |