US4048141A
Expired / Lapsed
US
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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: 1976-01-19
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Granted: 1977-09-13
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Expires: 1996-01-19
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
2026-10-27 07:26
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/68; C08G59/688; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/54; C07F9/5407; C08G59/40; C08G59/42; C08G59/423; Y; Y10; Y10S; Y10S260/00; Y10S260/24
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
105 words
A precatalyzed epoxy resin composition comprising (a) an epoxy resin bearing an average of more than one vicinal epoxy group per molecule and (b) a small but catalytic amount of a phosphorus-containing catalyst of the formula ##STR16## 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 - is a compatible anion.
Claim 2
Dependent Claim
105 words
A precatalyzed epoxy resin composition comprising (a) an epoxy resin bearing an average of more than one vicinal epoxy group per molecule and (b) a small but catalytic amount of a phosphorus-containing catalyst of the formula ##STR16## 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 - is a compatible anion.
Claim 3
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 4
Dependent Claim
24 words
The composition defined by claim 2 wherein R 2 -R 4 are each n-butyl; R 6 is hydrogen; and n is 0 or 1.
Claim 5
Dependent Claim
31 words
The composition defined by claim 3 wherein (b) 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 6
Dependent Claim
30 words
The composition defined by claim 1 wherein (a) is the reaction product of 4,4'-isopropylidenediphenol and epichlorohydrin, and (b) is a 3-triphenylphosphoranylidene or a 3-tri-n-butylphosphoranylidene dihydro-2,5-furandione or a hydrolyzed derivative thereof.
Claim 7
Dependent Claim
102 words
A composition comprising (a) an epoxide bearing at least one vicinal epoxy group per molecule; (b) a phenol and (c) a small but catalytic amount of a phosphorus-containing catalyst corresponding to the formula ##STR17## 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 - is a compatible anion.
Claim 8
Dependent Claim
102 words
A composition comprising (a) an epoxide bearing at least one vicinal epoxy group per molecule; (b) a phenol and (c) a small but catalytic amount of a phosphorus-containing catalyst corresponding to the formula ##STR17## 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 - is a compatible anion.
Claim 9
Dependent Claim
33 words
The composition defined by claim 6 wherein (a) is an epoxy resin and (b) is a polyhydric phenol of from 6 to about 30 carbon atoms bearing from 2 to 6 hydroxyl groups.
Claim 10
Dependent Claim
53 words
The composition defined by claim 7 wherein (b) is a polyhydric phenol corresponding to the formula ##STR18## wherein G is hydrogen, fluoro, chloro, bromo or hydrocarbyl and X is oxygen, sulfur, --SO--, --SO 2 --, bivalent hydrocarbon radicals containing up to 10 carbon atoms, or a bivalent oxygen-, sulfur- or nitrogen-containing hydrocarbon radical.
Claim 11
Dependent Claim
10 words
The composition defined by claim 8 wherein (b) is 4,4'-isopropylidenediphenol.
Claim 12
Dependent Claim
53 words
The composition defined by claim 9 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 13
Dependent Claim
65 words
The composition defined by claim 6 wherein (a) is an epoxy resin corresponding to the formula ##STR19## 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 ##STR20##
Claim 14
Dependent Claim
31 words
The composition defined by claim 6 wherein (a) is an alkylene oxide of from 2 to 4 carbon atoms or a mixture thereof and (b) is phenol or an alkylated phenol.
Claim 15
Dependent Claim
34 words
The composition defined by claim 6 wherein (a) is an epoxy resin corresponding to the formula ##STR21## wherein R' is hydrogen or an alkyl radical and m is from about 0.1 to about 10.
Claim 16
Dependent Claim
15 words
The composition defined by claim 13 wherein m is from about 1 to about 2.
Claim 17
Dependent Claim
38 words
The composition defined by claim 6 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 18
Dependent Claim
24 words
The composition defined by claim 15 wherein R 2 -R 4 are each n-butyl; R 6 is hydrogen; and n is 0 or 1.
Claim 19
Dependent Claim
31 words
The composition defined by claim 16 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 20
Dependent Claim
31 words
The composition defined by claim 6 wherein (a) is the diglycidyl ether of 4,4'-isopropylidenediphenol, (b) is 4,4'-isopropylidenediphenol and (c) is a 3-triphenylphosphoranylidene or a 3-tri-n-butylphosphoranylidene dihydro-2,5-furandione or a hydrolyzed derivative thereof.
Claim 21
Dependent Claim
31 words
The composition defined by claim 6 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 22
Dependent Claim
31 words
The composition defined by claim 19 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)
US3400098A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-09-12 | 1981-03-14 | 1981-09-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-09-12 | 1985-03-14 | 1985-09-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-09-12 | 1989-03-14 | 1989-09-13 | $7700.00 | Window Closed / Lapsed |