US4499234A
Expired / Lapsed
US
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Non-corrosive silicone RTV compositions
Assignee: General Electric Co
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Filing: 1983-10-14
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Granted: 1985-02-12
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Expires: 2003-10-14
Abstract
Abstract Stable, substantially acid-free, one package, moisture curable RTV compositions are provided having a scavenger for chemically combined hydroxy groups of the formula ##STR1## where x equals 1 or 2 and y equals 0 to 3 inclusive. A method for providing the aforesaid moisture curable RTV compositions is also provided. Novel compounds of the formula ##STR2## where x equals 1 or 2 and y equals 0 to 2 inclusive are provided as are methods for making such novel compounds.
Inventors
- 👤 Sandra L. Pratt
- 👤 Gary M. Lucas
- 👤 Michio Zembayashi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 01:52
CPC Classifications
C; C08; C08L; C08L83/00; C08L83/04; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804; C08G; C08G77/00; C08G77/04; C08G77/14; C08G77/16; Y; Y10; Y10S; Y10S528/00; Y10S528/901
Claims Analysis
Total Claims: 38
Claim 1
Independent Claim
160 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: (a) a polydiorganosiloxane base polymer, (b) an effective amount of condensation catalyst, and (c) a stabilizing amount of scavenger for hydroxy functional groups having the formula ##STR22## where R is a substituted or unsubstituted organo group having at least two carbon atoms; R 1 is a hydrolyzable leaving group selected from the group consisting of alkoxy, amido, amino, carbamato, enoxy, imidato, isocyanato, oximato, thioisocyanato, and ureido; R 2 and R 3 are independently selected C 1-13 monovalent substituted or unsubstituted hydrocarbon radicals; R 4 is a hydrolyzable leaving group selected from the group consisting of alkoxy, amido, amino, carbamato, enoxy, imidato, isocyanato, oximato, thioisocyanato and ureido; x is equal to 1 or 2 and y is equal to 0 to 3 inclusive.
Claim 2
Dependent Claim
160 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: (a) a polydiorganosiloxane base polymer, (b) an effective amount of condensation catalyst, and (c) a stabilizing amount of scavenger for hydroxy functional groups having the formula ##STR22## where R is a substituted or unsubstituted organo group having at least two carbon atoms; R 1 is a hydrolyzable leaving group selected from the group consisting of alkoxy, amido, amino, carbamato, enoxy, imidato, isocyanato, oximato, thioisocyanato, and ureido; R 2 and R 3 are independently selected C 1-13 monovalent substituted or unsubstituted hydrocarbon radicals; R 4 is a hydrolyzable leaving group selected from the group consisting of alkoxy, amido, amino, carbamato, enoxy, imidato, isocyanato, oximato, thioisocyanato and ureido; x is equal to 1 or 2 and y is equal to 0 to 3 inclusive.
Claim 3
Dependent Claim
41 words
The composition of claim 1 wherein R is a C 2-13 aliphatic organic radical selected from the group consisting of alkyl, alkenyl, alkynyl, alkylether, alkylester, alkylketone and alkylcyano or a C 6-30 aromatic organic radical selected from aryl, aralkyl and alkaryl.
Claim 4
Dependent Claim
38 words
The composition of claim 1 wherein R is a C 3-8 linear aliphatic organic radical selected from the group consisting of alkyl, alkylether and alkylketone or a C 6-18 aromatic organic radical selected from aryl, aralkyl and alkaryl.
Claim 5
Dependent Claim
15 words
The composition of claim 1 wherein R 1 has from 1 to 13 carbon atoms.
Claim 6
Dependent Claim
15 words
The composition of claim 1 wherein R 1 has from 1 to 8 carbon atoms.
Claim 7
Dependent Claim
20 words
The composition of claim 1 wherein R 2 and R 3 have from 1 to about 4 carbon atoms, respectively.
Claim 8
Dependent Claim
18 words
The composition of claim 1 wherein R 2 and R 3 are independently selected from methyl and ethyl.
Claim 9
Dependent Claim
15 words
The composition of claim 1 wherein R 4 has from 1 to 13 carbon atoms.
Claim 10
Dependent Claim
15 words
The composition of claim 1 wherein R 4 has from 1 to 8 carbon atoms.
Claim 11
Dependent Claim
23 words
The composition of claim 1 wherein the scavenger for hydroxy functional groups is selected from the group consisting of: 1,1-dimethoxy-2-(dimethylmethoxysilyl)-2-sila-1-azacyclopentane, 1,1-diethoxy-2-(diethylethoxysilyl)-2-sila-1-azacyclopentane and 1,1-diethoxy-2-(dimethylethoxysilyl)-2-sila-1-azacyclopentane.
Claim 12
Dependent Claim
13 words
The composition of claim 1 wherein the polydiorganosiloxane base polymer is silanol terminated.
Claim 13
Dependent Claim
110 words
The composition of claim 11 wherein the scavenger for hydroxy functional groups has the formula ##STR23## where R is a substituted or unsubstituted organo group having at least two carbon atoms, R 1 is a hydrolyzable leaving group selected from the group consisting of alkoxy, amido, amino, carbamato, enoxy, imidato, isocyanato, oximato, thioisocyanato and ureido, R 2 and R 3 are independently selected C 1-13 monovalent substituted or unsubstituted hydrocarbon radicals, R 4 is a hydrolyzable leaving group selected from the group consisting of alkoxy, amido, amino, carbamato, enoxy, imidato, isocyanato, oximato, thioisocyanato and ureido, x is equal to 1 or 2 and y is equal to 0 or 1.
Claim 14
Dependent Claim
64 words
The composition of claim 11 further comprising an effective amount of crosslinking silane of the formula ##STR24## where R 5 is a C 1-8 aliphatic organic radical selected from the group consisting of alkyl, alkylether, alkyester, alkylketone and alkylcyano radicals or a C 7-13 aralkyl radical, R 6 is a C 1-13 monovalent substituted or unsubstituted hydrocarbon radical and b equals 0 or 1.
Claim 15
Dependent Claim
170 words
The composition of claim 11 wherein the scavenger for hydroxy functional groups has the formula ##STR25## where R is a substituted or unsubstituted organo group having at least two carbon atoms, R 1 is a hydrolyzable leaving group selected from the group consisting of alkoxy, amido, amino, carbamato, enoxy, imidato, isocyanato, oximato, thioisocyanato and ureido radicals, R 2 and R 3 are independently selected C 1-13 monovalent substituted or unsubstituted hydrocarbon radicals, R 4 is a hydrolyzable leaving group selected from the group consisting of alkoxy, amido, amino, carbamato, enoxy, imidato, isocyanato, oximato, thioisocyanato and ureido, x is equal to 1 or 2 and y is equal to 2 or 3; further comprising an effective amount of crosslinking silane of the formula ##STR26## where R 5 is a C 1-8 aliphatic organic radical selected from the group consisting of alkyl, alkylether, alkylester, alkylketone, and alkylcyano radicals or a C 7-13 aralkyl radical, R 6 is a C 1-13 monovalent substituted or unsubstituted hydrocarbon radical and b equals 0 or 1.
Claim 16
Dependent Claim
22 words
The composition of claim 1 wherein the polydiorganosiloxane base polymer is terminated at each chain end with at least two hydrolyzable groups.
Claim 17
Dependent Claim
12 words
The composition of claim 15 wherein the hydrolyzable groups are alkoxy groups.
Claim 18
Dependent Claim
13 words
The composition of claim 1 wherein the condensation catalyst is a tin compound.
Claim 19
Dependent Claim
12 words
The composition of claim 17 wherein the tin condensation catalyst is dibutyltindi-t-butoxide.
Claim 20
Dependent Claim
39 words
The composition of claim 1 further comprising a filler selected from the group consisting of titantium dioxide, zirconium silicate, silica aerogel, iron oxide, diatomaceous earth, fumed silica, carbon black, precipitated silica, glass fibers, polyvinylchloride, ground quartz and calcium carbonate.
Claim 21
Dependent Claim
10 words
The composition of claim 1 further comprising an adhesion promoter.
Claim 22
Dependent Claim
28 words
The composition of claim 20 wherein the adhesion promoter is selected from the group consisting of: 3-(2-aminoethyl)aminopropyltrimethoxysilane, γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, tris-(trimethoxysilylpropyl)isocyanurate, γ-glycidoxypropyltrimethoxysilane, β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, vinyltrimethoxysilane, γ-isocyanatopropyltrimethoxysilane, β-cyanoethyltrimethoxysilane, γ-methacryloxypropyltrimethoxysilane and acetoxypropyltrimethoxysilane.
Claim 23
Dependent Claim
11 words
The composition of claim 1 further comprising a sag control agent.
Claim 24
Dependent Claim
9 words
The composition of claim 1 further comprising a plasticizer.
Claim 25
Dependent Claim
10 words
The composition of claim 1 further comprising a cure accelerator.
Claim 26
Independent Claim
179 words
A method for making a stable, one package, substantially anhydrous and substantially acid-free, room temperature vulcanizable organopolysiloxane composition curable to the solid elastomeric state, which method comprises agitating under substantially anhydrous conditions at a temperature in the range of from 0° C. to 180° C., a room temperature vulcanizable material comprising a mixture of: (a) 100 parts of a polydiorganosiloxane base polymer, (b) an effective amount of condensation catalyst, and (c) a stabilizing amount of scavenger for hydroxy functional groups having the formula ##STR27## where R is a substituted or unsubstituted organo group having at least two carbon atoms, R 1 is a hydrolyzable leaving group selected from the group consisting of alkoxy, amido, amino, carbamato, enoxy, imidato, isocyanato, oximato, thioisocyanato and ureido; R 2 and R 3 are independently selected C 1-13 monovalent substituted or unsubstituted hydrocarbon radicals, R 4 is a hydrolyzable leaving group selected from the group consisting of alkoxy, amido, amino, carbamato, enoxy, imidato, isocyanato, oximato, thioisocyanato and ureido, x is equal to 1 or 2 and y is equal to 0 to 3 inclusive.
Claim 27
Independent Claim
179 words
A method for making a stable, one package, substantially anhydrous and substantially acid-free, room temperature vulcanizable organopolysiloxane composition curable to the solid elastomeric state, which method comprises agitating under substantially anhydrous conditions at a temperature in the range of from 0° C. to 180° C., a room temperature vulcanizable material comprising a mixture of: (a) 100 parts of a polydiorganosiloxane base polymer, (b) an effective amount of condensation catalyst, and (c) a stabilizing amount of scavenger for hydroxy functional groups having the formula ##STR27## where R is a substituted or unsubstituted organo group having at least two carbon atoms, R 1 is a hydrolyzable leaving group selected from the group consisting of alkoxy, amido, amino, carbamato, enoxy, imidato, isocyanato, oximato, thioisocyanato and ureido; R 2 and R 3 are independently selected C 1-13 monovalent substituted or unsubstituted hydrocarbon radicals, R 4 is a hydrolyzable leaving group selected from the group consisting of alkoxy, amido, amino, carbamato, enoxy, imidato, isocyanato, oximato, thioisocyanato and ureido, x is equal to 1 or 2 and y is equal to 0 to 3 inclusive.
Claim 28
Dependent Claim
41 words
The method of claim 25 wherein R is a C 2-13 aliphatic organic radical selected from the group consisting of alkyl, alkenyl, alkynyl, alkylether, alkylester, alkylketone and alkylcyano or a C 6-30 aromatic organic radical selected from aryl, aralkyl, and alkaryl.
Claim 29
Dependent Claim
15 words
The method of claim 25 wherein R 1 has from 1 to 13 carbon atoms.
Claim 30
Dependent Claim
20 words
The method of claim 25 wherein R 2 and R 3 have from 1 to about 4 carbon atoms, respectively.
Claim 31
Dependent Claim
15 words
The method of claim 25 wherein R 4 has from 1 to 13 carbon atoms.
Claim 32
Dependent Claim
23 words
The method of claim 25 wherein the scavenger for hydroxy functional groups is selected from the group consisting of: 1,1-dimethoxy-2-(dimethylmethoxysilyl)-2-sila-1-azacyclopentane, 1,1-diethoxy-2-(diethylethoxysilyl)-2-sila-1-azacyclopentane and 1,1-diethoxy-2-(dimethylethoxysilyl)-2-sila-1-azacyclopentane.
Claim 33
Dependent Claim
84 words
The method of claim 25 further comprising adding and agitating under substantially anhydrous conditions at a temperature in the range of from 0° C. to 180° C., an effective amount of crosslinking silane of the formula ##STR28## where R 5 is a C 1-8 aliphatic organic radical selected from the group consisting of alkyl, alkylether, alkylester, alkylketone and alkylcyano radicals or a C 7-13 aralkyl radical; R 6 is a C 1-13 monovalent substituted or unsubstituted hydrocarbon radical and b equals 0 or 1.
Claim 34
Dependent Claim
59 words
The method of claim 25 further comprising adding and agitating under substantially anhydrous conditions at a temperature in the range of from 0° C. to 180° C., a filler selected from the group consisting of titanium dioxide, zirconium silicate, silica aerogel, iron oxide, diatomaceous earth, fumed silica, carbon black, precipitated silica, glass fibers, polyvinylchloride, ground quartz and calcium carbonate.
Claim 35
Dependent Claim
48 words
The method of claim 25 further comprising adding and agitating under substantially anhydrous conditions at a temperature in the range of from 0° C. to 180° C., an adhesion promoter selected from the group consisting of: 3-(2-aminoethyl)aminopropyltrimethoxysilane, γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, tris-(trimethoxysilylpropyl)isocyanurate, γ-glycidoxypropyltrimethoxysilane, β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, vinyltrimethoxysilane, γ-isocyanatopropyltrimethoxysilane, β-cyanoethyltrimethoxysilane, γ-methacryloxypropyltrimethoxysilane and acetoxypropyltrimethoxysilane.
Claim 36
Dependent Claim
31 words
The method of claim 25 further comprising adding and agitating under substantially anhydrous conditions at a temperature in the range of from 0° C. to 180° C., a sag control agent.
Claim 37
Dependent Claim
29 words
The method of claim 25 further comprising adding and agitating under substantially anhydrous conditions at a temperature in the range of from 0° C. to 180° C., a plasticizer.
Claim 38
Dependent Claim
30 words
The method of claim 25 further comprising adding and agitating under substantially anhydrous conditions at a temperature in the range of from 0° C. to 180° C., a cure accelerator.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-02-12 | 1988-08-13 | 1989-02-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-02-12 | 1992-08-13 | 1993-02-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-02-12 | 1996-08-13 | 1997-02-12 | $7700.00 | Window Closed / Lapsed |