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US4554342A
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Heat-curable compositions comprising an epoxy resin, an amine and a sulfonium salt
Assignee: Resolution Performance Products LLC
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Filing: 1984-07-30
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Granted: 1985-11-19
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Expires: 2004-07-30
Abstract
Abstract Heat-curable compositions exhibiting improved thermal pot life are obtained from epoxy compositions comprising (1) a polyepoxide, (2) an aromatic or aliphatic amine and (3) a trihydrocarbyl sulfonium salt.
Inventors
- 👤 Larry S. Corley
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 08:37
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/68; C08G59/687; C08G59/40; C08G59/50; C08G59/5006; C08G59/5033
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
47 words
A curable composition consisting essentially of (a) a polyepoxide, (b) at least one aromatic or aliphatic amine present in an amount effective to cure the polyepoxide under curing conditions, and (c) a catalytic amount of a trihydrocarbyl sulfonium salt comprising substituted or unsubstituted alkyl or aryl radicals.
Claim 2
Dependent Claim
47 words
A curable composition consisting essentially of (a) a polyepoxide, (b) at least one aromatic or aliphatic amine present in an amount effective to cure the polyepoxide under curing conditions, and (c) a catalytic amount of a trihydrocarbyl sulfonium salt comprising substituted or unsubstituted alkyl or aryl radicals.
Claim 3
Dependent Claim
16 words
The composition of claim 1 wherein the polyepoxide is a glycidyl polyether of a polyhydric phenol.
Claim 4
Dependent Claim
11 words
The composition of claim 2 wherein the polyhydric phenol is 2,2bis(4-hydroxyphenyl)propane.
Claim 5
Dependent Claim
15 words
The composition of claim 1 wherein the trihydrocarbyl sulfonium salt is a trialkyl sulfonium salt.
Claim 6
Dependent Claim
26 words
The composition of claim 4 wherein the trialkyl sulfonium salt is used in an amount from about 0.001% to about 10% by weight of the polyepoxide.
Claim 7
Dependent Claim
22 words
The composition of claim 1 wherein the trihydrocarbyl sulfonium salt is a mixture prepared by the condensation of 2,2'-thiodiethanol with tetrafluoroboric acid.
Claim 8
Dependent Claim
13 words
The composition of claim 1 wherein the trihydrocarbyl sulfonium salt is ethyl(2-hydroxyethyl)(2-(ethylthio)ethyl)sulfonium tetrafluoroborate.
Claim 9
Dependent Claim
11 words
The composition of claim 1 wherein the aromatic amine is 4,4'-methylenedianiline.
Claim 10
Dependent Claim
65 words
A composition consisting essentially of: (a) a polyepoxide, (b) an aromatic or aliphatic amine present in an amount of from about 0.5 to about 2.0 chemical equivalents based on the polyepoxide, and (c) a trihydrocarbyl sulfonium salt comprising substituted or unsubstituted alkyl or aryl radicals and present in an amount of about 0.001 to about 10 weight percent based on the weight of the polyepoxide.
Claim 11
Dependent Claim
65 words
A composition consisting essentially of: (a) a polyepoxide, (b) an aromatic or aliphatic amine present in an amount of from about 0.5 to about 2.0 chemical equivalents based on the polyepoxide, and (c) a trihydrocarbyl sulfonium salt comprising substituted or unsubstituted alkyl or aryl radicals and present in an amount of about 0.001 to about 10 weight percent based on the weight of the polyepoxide.
Claim 12
Dependent Claim
26 words
The composition of claim 9 wherein the amine is present in an amount of from about 0.5 to about 1.5 chemical equivalents based on the polyepoxide.
Claim 13
Dependent Claim
33 words
The composition of claim 9 wherein the amine is selected from the group consisting of methylenedianiline, metaphenylenediamine, 2,4-bis[p-aminobenzyl]aniline, diaminodiphenyl sulfone, 2,4-toluenediamine, 1,3-diamino-2,4-diethyl-6-methylbenzene, 4,4'-oxydianiline, methylenebis(ortho-chloroaniline), 2,6-diaminopyridine, 4-bromo-1,3-diaminobenzene, bis(4-aminocyclohexyl)methane, 1,8-diamino-p-menthane, 1,2-diaminocyclohexane and mixtures of these.
Claim 14
Dependent Claim
28 words
The composition of claim 9 in which the amine is present in an amount of from about 0.75 to about 1.25 equivalents of amine per equivalent of polyepoxy.
Claim 15
Dependent Claim
39 words
The composition of claim 9 which further contains at least one additive selected from the group consisting of a filler, reinforcement fibers, a pigment, a flame retardant, a plasticizer, a stabilizer, an extender, a thixotropic agent and an antioxidant.
Claim 16
Dependent Claim
10 words
The composition of claim 9 which further contains reinforcement fibers.
Claim 17
Independent Claim
45 words
A method for extending the pot life of a heat-curable polyepoxide composition containing an amine curing agent comprising contacting the composition with a material consisting essentially of from about 0.5 to about 2.0 chemical equivalents of at least one substituted or unsubstituted trihydrocarbyl sulfonium salt.
Claim 18
Independent Claim
45 words
A method for extending the pot life of a heat-curable polyepoxide composition containing an amine curing agent comprising contacting the composition with a material consisting essentially of from about 0.5 to about 2.0 chemical equivalents of at least one substituted or unsubstituted trihydrocarbyl sulfonium salt.
Claim 19
Dependent Claim
36 words
The method of claim 15 in which the amine curing agent is selected from the group consisting of methylenedianiline, metaphenylenediamine, 2,4-bis[p-aminobenzyl]aniline, diaminodiphenyl sulfone, 2,4-toluenediamine, 1,3-diamino-2,4-diethyl-6-methylbenzene, 4,4'-oxydianiline, methylenebis(ortho-chloroaniline), 2,6-diaminopyridine, 4-bromo-1,3-diaminobenzene, bis(4-aminocyclohexyl)methane, 1,8-diamino-p-menthane, 1,2-diaminocyclohexane and mixtures of these.
Claim 20
Dependent Claim
23 words
The method of claim 15 in which the trihydrocarbyl sulfonium salt is a mixture prepared by the condensation of 2,2-thiodiethanol with tetrafluoroboric acid.
Claim 21
Dependent Claim
13 words
The method of claim 16 in which the composition further contains reinforcement fibers.
Claim 22
Dependent Claim
79 words
The method of claim 16 in which the trihydrocarbyl sulfonium salt can be represented by the formula ##STR4## wherein R 1 , R 2 and R 3 are selected independently from substituted or unsubstituted alkyl and aryl radicals having 1 to about 18 carbon atoms and X is selected from the group consisting of BF 4 , PF 6 , AsF 6 , CF 3 SO 3 , FSO 3 , CH 3 SO 3 , 2,4,6-trinitrobenzenesulfonate and p-toluenesulfonate.
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) | 1988-11-18 | 1989-05-20 | 1989-11-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-11-18 | 1993-05-20 | 1993-11-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-11-18 | 1997-05-20 | 1997-11-19 | $7700.00 | Window Closed / Lapsed |