Patent US4131633A successfully refreshed from Google Patents.
US4131633A
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Latent catalysts for promoting reaction of epoxides with phenols and/or carboxylic acids
Assignee: Dow Chemical Co
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Filing: 1977-04-11
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Granted: 1978-12-26
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Expires: 1997-04-11
Abstract
Abstract Certain phosphorus-containing compounds are described herein which are novel latent catalysts for promoting the reaction between vicinal epoxides and phenols and/or carboxylic acids (or anhydrides). Precatalyzed epoxy resins are easily prepared using such catalysts.
Inventors
- 👤 George A. Doorakian
- 👤 Dennis L. Schmidt
- 👤 Martin C. Cornell, III
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 17:09
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/68; C08G59/688; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/535; C07F9/54; C07F9/5407; C07F9/5442; C08G59/40; C08G59/42; C08G59/423
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
125 words
A composition comprising (a) an epoxide bearing at least one vicinal epoxy group per molecule; (b) (1) an organic carboxylic acid or anhydride of said acid or (2) a mixture of a phenol and an organic carboxylic acid or anhydride of said acid, and (c) a small but catalytic amount of phosphorus-containing catalyst corresponding to the formula ##STR15## or a mixture thereof, wherein: R 1 is hydrogen or hydrocarbyl, R 2 -r 4 are hydrocarbyl groups, with the proviso that R 2 -R 4 are not each aryl in formula VII, R 5 is hydrogen or alkyl, R 6 is hydrogen, alkyl, carboxy, or alkoxy carbonyl, R 7 is hydrogen or hydrocarbyl, n is from 0 to about 20, and A.sup.⊖ is a compatible anion.
Claim 2
Dependent Claim
125 words
A composition comprising (a) an epoxide bearing at least one vicinal epoxy group per molecule; (b) (1) an organic carboxylic acid or anhydride of said acid or (2) a mixture of a phenol and an organic carboxylic acid or anhydride of said acid, and (c) a small but catalytic amount of phosphorus-containing catalyst corresponding to the formula ##STR15## or a mixture thereof, wherein: R 1 is hydrogen or hydrocarbyl, R 2 -r 4 are hydrocarbyl groups, with the proviso that R 2 -R 4 are not each aryl in formula VII, R 5 is hydrogen or alkyl, R 6 is hydrogen, alkyl, carboxy, or alkoxy carbonyl, R 7 is hydrogen or hydrocarbyl, n is from 0 to about 20, and A.sup.⊖ is a compatible anion.
Claim 3
Dependent Claim
55 words
The composition defined by claim 1 wherein (a) is an epoxy resin and (b) is (1) a polyhydric phenol of from 6 to about 30 carbon atoms bearing from 2 to 6 hydroxyl groups, (2) an ethylenically unsaturated monocarboxylic acid or anhydride thereof (3) a polybasic carboxylic acid, or anhydride thereof or any mixture thereof.
Claim 4
Dependent Claim
53 words
The composition defined by claim 1 wherein (a) is the diglycidyl ether of 4,4'-isopropylidenediphenol, and (c) is 3-triphenyl- or 3-tri-n-butylphosphoranylidene dihydro-2,5-furandione or a hydrolyzed derivative thereof and wherein (c) is present in an amount of from about 0.05 to about 5 percent by weight, based on the combined weights of (a) and (b).
Claim 5
Dependent Claim
17 words
The composition defined by claim 1 wherein (b) is an ethylenically unsaturated monocarboxylic acid or anhydride thereof.
Claim 6
Dependent Claim
13 words
The composition defined by claim 4 wherein (b) is acrylic or methacrylic acid.
Claim 7
Dependent Claim
17 words
The composition defined by claim 1 wherein (b) is a polybasic organic carboxylic acid or anhydride thereof.
Claim 8
Dependent Claim
16 words
The composition defined by claim 6 wherein (b) is succinic, maleic or hexahydrophthalic acid or anhydride.
Claim 9
Dependent Claim
65 words
The composition defined by claim 1 wherein (a) is an epoxy resin corresponding to the formula ##STR16## wherein R', R 1 ', R 2 ' and R 3 ' are independently selected from hydrogen, bromine and chlorine and wherein A' is an alkylene or alkylidene group having from about 1 to about 4 carbon atoms, or A' is a divalent radical of the formula ##STR17##
Claim 10
Dependent Claim
31 words
The composition defined by claim 1 wherein (a) is an alkylene oxide of from 2 to 4 carbon atoms or a mixture thereof and (b) is acrylic acid or methacrylic acid.
Claim 11
Dependent Claim
34 words
The composition defined by claim 1 wherein (a) is an epoxy resin corresponding to the formula ##STR18## wherein R' is hydrogen or an alkyl radical and m is from about 0.1 to about 10.
Claim 12
Dependent Claim
15 words
The composition defined by claim 10 wherein m is from about 1 to about 2.
Claim 13
Dependent Claim
38 words
The composition defined by claim 1 wherein R 1 is hydrogen; R 2 -R 4 are alkyl; R 5 is hydrogen; R 6 is hydrogen or carboxy; R 7 is hydrogen; and n is 0, 1 or 2.
Claim 14
Dependent Claim
24 words
The composition defined by claim 12 wherein R 2 -R 4 are each n-butyl; R 6 is hydrogen; and n is 0 or 1.
Claim 15
Dependent Claim
31 words
The composition defined by claim 13 wherein (c) is 3-tri-n-butylphosphoranylidene dihydro-2,5-furandione; tri-n-butyl(1,2-dicarboxyethyl)phosphonium hydroxide, inner salt; a tri-n-butyl(2-carboxyethyl)phosphonium salt tri-n-butyl(2-carboxyethyl)phosphonium hydroxide, inner salt; a tri-n-butyl(carboxymethyl)phosphonium salt; or tri-n-butyl (carboxymethyl)phosphonium hydroxide, inner salt.
Claim 16
Dependent Claim
31 words
The composition defined by claim 1 wherein (c) is present in amounts of from about 0.001 to about 10 percent by weight, based on the combined weights of (a) and (b).
Claim 17
Dependent Claim
31 words
The composition defined by claim 15 wherein (c) is present in amounts of from about 0.05 to about 5 percent by weight, based on the combined weights of (a) and (b).
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) | 1981-12-25 | 1982-06-26 | 1982-12-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-12-25 | 1986-06-26 | 1986-12-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-12-25 | 1990-06-26 | 1990-12-26 | $7700.00 | Window Closed / Lapsed |