US3971747A
Expired / Lapsed
US
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Curable compositions
Assignee: Dow Silicones Corp
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Filing: 1975-04-11
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Granted: 1976-07-27
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Expires: 1995-04-11
Abstract
Abstract Certain aluminum compounds, such as aluminum alkoxides, chelates and acylates, catalyst the reaction of .tbd.SiOH with ##EQU1## to yield compositions containing ##EQU2## LINKAGES.
Inventors
- 👤 Howard M. Bank
- 👤 Keith W. Michael
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 02:29
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/68; C08G59/70; C08G59/40; C08G59/4007; C08G59/4085; C08G59/681; C08K; C08K5/00; C08K5/04; C08K5/05; C08K5/09; C08K5/10; C08K5/11; C08K5/54; C08L; C08L63/00; C08L83/00; C08L83/04
Claims Analysis
Total Claims: 38
Claim 1
Independent Claim
319 words
A method of preparing compositions containing silicon-oxygen-carbon bonds comprising reacting under substantially anhydrous conditions A. an organosilicon compound containing at least one .tbd.SiOH group with B. a compound containing at least one epoxy group, said reaction being carried out in the presence of a catalytic amount of C. an aluminum compound selected from the group consisting of a. al(OR) 3 in which R is either a hydrogen atom or selected from the group consisting of alkyl radicals contaning from 1 to 20 inclusive carbon atoms or aryl and aryl-containing hydrocarbon radicals containing from 6 to 24 inclusive carbon atoms; ##EQU29## in which R is as previously defined, R' is selected from the group consisting of the hydrogen atom, alkyl radicals containing from 1 to 30 inclusive carbon atoms and aryl or aryl-containing radicals of at least 6 carbon atoms, n having a value of from 0 to 2 and condensates of such compounds; c. aluminum salts of the formula H.sup.+ Al.sup.-(OR).sub.4 in which R is as previously defined; d. aluminosiloxy compounds of the formula =ALOSIR.sub.3.sup.2 in which R 2 is selected from the group consisting of --OR radicals in which R is as defined, ##EQU30## radicals in which R' is as defined, monovalent hydrocarbon or halohydrocarbon radicals containing from 1 to 30 inclusive carbon atoms, and siloxane moieties of the formula ##EQU31## in which R 3 is selected from the group consisting of OR radicals in which R is as defined, ##EQU32## radicals in which R' is as defined and monovalent hydrocarbon or halohydrocarbon radicals containing from 1 to 30 inclusive carbon atoms, and a has a value of from 1 to 3; The remaining aluminum valences being satisfied by --OAl=, --OR, ##EQU33## or --OSIR 3 2 bonding, R, R' and R 2 being as previously defined; and e. aluminum chelates formed by reacting compounds (a), (b) or (c) with sequestering agents in which the coordinating atoms are oxygen.
Claim 2
Independent Claim
319 words
A method of preparing compositions containing silicon-oxygen-carbon bonds comprising reacting under substantially anhydrous conditions A. an organosilicon compound containing at least one .tbd.SiOH group with B. a compound containing at least one epoxy group, said reaction being carried out in the presence of a catalytic amount of C. an aluminum compound selected from the group consisting of a. al(OR) 3 in which R is either a hydrogen atom or selected from the group consisting of alkyl radicals contaning from 1 to 20 inclusive carbon atoms or aryl and aryl-containing hydrocarbon radicals containing from 6 to 24 inclusive carbon atoms; ##EQU29## in which R is as previously defined, R' is selected from the group consisting of the hydrogen atom, alkyl radicals containing from 1 to 30 inclusive carbon atoms and aryl or aryl-containing radicals of at least 6 carbon atoms, n having a value of from 0 to 2 and condensates of such compounds; c. aluminum salts of the formula H.sup.+ Al.sup.-(OR).sub.4 in which R is as previously defined; d. aluminosiloxy compounds of the formula =ALOSIR.sub.3.sup.2 in which R 2 is selected from the group consisting of --OR radicals in which R is as defined, ##EQU30## radicals in which R' is as defined, monovalent hydrocarbon or halohydrocarbon radicals containing from 1 to 30 inclusive carbon atoms, and siloxane moieties of the formula ##EQU31## in which R 3 is selected from the group consisting of OR radicals in which R is as defined, ##EQU32## radicals in which R' is as defined and monovalent hydrocarbon or halohydrocarbon radicals containing from 1 to 30 inclusive carbon atoms, and a has a value of from 1 to 3; The remaining aluminum valences being satisfied by --OAl=, --OR, ##EQU33## or --OSIR 3 2 bonding, R, R' and R 2 being as previously defined; and e. aluminum chelates formed by reacting compounds (a), (b) or (c) with sequestering agents in which the coordinating atoms are oxygen.
Claim 3
Dependent Claim
13 words
A method in accordance with claim 1 wherein (A) is a hydroxy-functional organopolysiloxane.
Claim 4
Dependent Claim
145 words
A method in accordance with claim 2 wherein (A) is of the formula ##EQU34## in which R 4 is a monovalent hydrocarbon radical selected from the group consisting of alkyl radicals of from 1 to 6 inclusive carbon atoms and the phenyl radical; R 5 is an alkyl radical of from 1 to 6 inclusive carbon atoms; a is an integer having a value of 1 or 2; b having a value of 0 or 1, the sum ofa + b being no more than 2; c is an integer having a value of 1 or 2, d is an integer having a value of from 1 to 3; e having a value of 0 to 2, the sum of d + 3 being no more than 3; x having a value of at least 1 and y having a value of 0 or more.
Claim 5
Dependent Claim
30 words
A method in accordance with claim 3 wherein the organopolysiloxane has from 1.0 to 1.7 R 4 substituents per silicon atom and contains at least 2 weight percent silanol groups.
Claim 6
Dependent Claim
12 words
A method in accordance with claim 2 wherein (B) is a polyepoxide.
Claim 7
Dependent Claim
15 words
A method in accordance with claim 5 wherein the polyepoxide (B) is a cycloaliphatic polyepoxide.
Claim 8
Dependent Claim
22 words
A method in accordance with claim 5 wherein the polyepoxide (B) is obtained by the reaction of polyhydric phenols with polyfunctional halohydrins.
Claim 9
Dependent Claim
21 words
A method in accordance with claim 7 wherein the polyepoxide (B) is obtained by the reaction of polyhydric phenols with epichlorohydrin.
Claim 10
Dependent Claim
16 words
A method in accordance with claim 1 wherein the aluminum compound is of the formula Al(OR).sub.3
Claim 11
Dependent Claim
16 words
a method in accordance with claim 1 wherein the aluminum compound is of the formula ##EQU35##
Claim 12
Dependent Claim
15 words
A method in accordance with claim 1 wherein the aluminum compound is an aluminum chelate.
Claim 13
Dependent Claim
19 words
A method in accordance with claim 1 wherein the aluminum compound is an aluminosiloxy compound of the formula .tbd.ALOSiR.sub.3.sup.2
Claim 14
Dependent Claim
35 words
A method in accordance with claim 1 wherein the aluminum catalyst is present in an amount in the range of from 0.05 to 5 weight percent based on the total weight of (A) + (B).
Claim 15
Dependent Claim
323 words
A substantially anhydrous composition comprising A. an organosilicon compound containing at least one silicon-bonded hydroxyl group; B. a compound containing at least one epoxy group; C. a catalytic amount of an aluminum compound selected from the group consisting of a. Al(OR) 3 in which R is either a hydrogen atom or selected from the group consisting of alkyl radicals containing from 1 to 20 inclusive carbon atoms or aryl and aryl-containing hydrocarbon radicals containing from 6 to 24 inclusive carbon atoms; ##EQU36## in which R is as previously defined, R' is selected from the group consisting of the hydrogen atom, alkyl radicals containing from 1 to 30 inclusive carbon atoms and aryl or aryl-containing radicals of at least 6 carbon atoms, n having a value of from 0 to 2 and condensates of such compounds; c. aluminum salts of the formula H.sup.+ Al.sup.-(OR).sub.4 in which R is as previously defined; d. aluminosiloxy compounds of the formula =ALOSiR.sub.3.sup.2 in which R 2 is selected from the group consisting of --OR radicals in which R is as defined, ##EQU37## radicals in which R' is as defined, monovalent hydrocarbon or halohydrocarbon radicals containing from 1 to 30 inclusive carbon atoms, and siloxane moieties of the formula ##EQU38## in which R 3 is selected from the group consisting of OR radicals in which R is as defined, ##EQU39## radicals in which R' is as defind and monovalent hydrocarbon or halohydrocarbon radicals containing from 1 to 30 inclusive carbon atoms, and a has a value of from 1 to 3; the remaining aluminum valences being satisfied by --OAl=, --OR, ##EQU40## or --OSIR 3 2 bonding, R, R' and R 2 being as previously defined; and e. aluminum chelates formed by reacting compounds (a), (b) or (c) with-sequestering agents in which the coordinating atom is oxygen, said organosilicon compond (A) being pesent in an amount sufficient to provide at least 0.1 .tbd.SiOH group per epoxy group present in (B).
Claim 16
Dependent Claim
323 words
A substantially anhydrous composition comprising A. an organosilicon compound containing at least one silicon-bonded hydroxyl group; B. a compound containing at least one epoxy group; C. a catalytic amount of an aluminum compound selected from the group consisting of a. Al(OR) 3 in which R is either a hydrogen atom or selected from the group consisting of alkyl radicals containing from 1 to 20 inclusive carbon atoms or aryl and aryl-containing hydrocarbon radicals containing from 6 to 24 inclusive carbon atoms; ##EQU36## in which R is as previously defined, R' is selected from the group consisting of the hydrogen atom, alkyl radicals containing from 1 to 30 inclusive carbon atoms and aryl or aryl-containing radicals of at least 6 carbon atoms, n having a value of from 0 to 2 and condensates of such compounds; c. aluminum salts of the formula H.sup.+ Al.sup.-(OR).sub.4 in which R is as previously defined; d. aluminosiloxy compounds of the formula =ALOSiR.sub.3.sup.2 in which R 2 is selected from the group consisting of --OR radicals in which R is as defined, ##EQU37## radicals in which R' is as defined, monovalent hydrocarbon or halohydrocarbon radicals containing from 1 to 30 inclusive carbon atoms, and siloxane moieties of the formula ##EQU38## in which R 3 is selected from the group consisting of OR radicals in which R is as defined, ##EQU39## radicals in which R' is as defind and monovalent hydrocarbon or halohydrocarbon radicals containing from 1 to 30 inclusive carbon atoms, and a has a value of from 1 to 3; the remaining aluminum valences being satisfied by --OAl=, --OR, ##EQU40## or --OSIR 3 2 bonding, R, R' and R 2 being as previously defined; and e. aluminum chelates formed by reacting compounds (a), (b) or (c) with-sequestering agents in which the coordinating atom is oxygen, said organosilicon compond (A) being pesent in an amount sufficient to provide at least 0.1 .tbd.SiOH group per epoxy group present in (B).
Claim 17
Dependent Claim
13 words
A composition in accordance with claim 14 wherein compound (B) is a polyepoxide.
Claim 18
Dependent Claim
150 words
A composition in accordance with claim 15 wherein component (A) is a hydroxy-functional organopolysiloxane of the formula ##EQU41## in which R 4 is a monovalent hydrocarbon radical selected from the group consisting of alkyl radicals of from 1 to 6 inclusive carbon atoms and the phenyl radical; R 5 is an alkyl radical of from 1 to 6 inclusive carbon atoms; a is an integer having a value of 1 or 2; b having a value of 0 or 1, the sum of a + b being no more than 2; c is an integer having a value of 1 or 2, d is an integer having a value of from 1 to 3; e having a value of 0 to 2, the sum of d + e being no more than 3; x having a value of at least 1 and y having a value of 0 or more.
Claim 19
Dependent Claim
30 words
A composition in accordance with claim 16 wherein the organopolysiloxane (A) is present in an amount sufficient to provide from 0.5 to 1.5 .tbd.SiOH per epoxy group present in (B).
Claim 20
Dependent Claim
45 words
A composition in accordance with claim 16 wherein said organopolysiloxane is a phenylpolysiloxane resin having a degree of substitution of from 1.0 to 1.7; a phenyl to silicon ratio of 0.2 to 1.5 and a silicon-bonded hydroxyl content of from 2.5 to 10 weight percent.
Claim 21
Dependent Claim
26 words
A composition in accordance with claim 18 wherein the polyepoxide (b) is selected from the group consisting of the glycidyl ethers of polyphenols and cycloaliphatic polyepoxides.
Claim 22
Dependent Claim
70 words
A composition in accordance with claim 19 wherein the phenylpolysiloxane resin is of the formula ##EQU42## in which R is an alkyl of from 1 to 3 inclusive carbon atoms, a has an average value of from 1.0 to 1.7, the phenyl to silicon ratio being in the range of 0.2 to 1.5, the silicon-bonded hydroxyl content of said resin being in the range of 2.5 to 7.5 weight percent.
Claim 23
Dependent Claim
11 words
A composition in accordance with claim 19 containing a solid filler.
Claim 24
Dependent Claim
32 words
A composition in accordance with claim 21 wherein the filler is present in an amount in the range of 30 to 90 weight percent based on the total weight of the composition.
Claim 25
Dependent Claim
17 words
A composition in accordance with claim 22 wherein the filler includes granular fused silica and glass fibers.
Claim 26
Dependent Claim
20 words
A composition in accordance with claim 20 wherein the aluminum catalyst (C) is an aluminum acylate of the formula ##EQU43##
Claim 27
Dependent Claim
49 words
A composition in accordance with claim 24 comprising A. from 10 to 60 weight percent of the polysiloxane resin B. from 49 to 90 weight percent of the polyepoxide C. from 0.1 to 5 weight percent, based on the combined weight of (A) and (B) of aluminum acylate catalyst.
Claim 28
Dependent Claim
17 words
A composition in accordance with claim 25 wherein the polyepoxide is an epoxy functional cresol novalac resin.
Claim 29
Dependent Claim
17 words
A composition in accordance with claim 25 wherein the polyepoxide is the diglycidyl ether of bis-phenol A.
Claim 30
Dependent Claim
22 words
A composition in accordance with claim 25 wherein the polyepoxide is a cycloaliphatic polyepoxide having an epoxide equivalent of more than 65.
Claim 31
Dependent Claim
24 words
A composition in accordance with claim 25 wherein the aluminum acylate (C) is selected from the group consisting of aluminum stearates and aluminum benzoates.
Claim 32
Dependent Claim
8 words
A cured composition in accordance with claim 15.
Claim 33
Dependent Claim
16 words
A composition in accordance with claim 14 wherein the aluminum compound is of the formula Al(OR).sub.3
Claim 34
Dependent Claim
17 words
A composition in accordance with claim 14 in which the aluminum compound is of the formula ##EQU44##
Claim 35
Dependent Claim
17 words
A composition in accordance with claim 14 wherein the aluminum compound is of the formula H.sup.+ Al.sup.-(OR).sub.4
Claim 36
Dependent Claim
16 words
A composition in accordance with claim 14 wherein the aluminum compound is of the formula .tbd.AlOSiR.sub.3.sup.2
Claim 37
Dependent Claim
15 words
a composition in accordance with claim 14 wherein the aluminum compound is an aluminum chelate.
Claim 38
Dependent Claim
20 words
A composition in accordance with claim 14 wherein at least a portion of the epoxide comprise a brominated epoxy compound.
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) | 1979-07-27 | 1980-01-26 | 1980-07-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-07-27 | 1984-01-26 | 1984-07-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-07-27 | 1988-01-26 | 1988-07-27 | $7700.00 | Window Closed / Lapsed |