US3948855A
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Process for reacting a phenol with a vicinal epoxy compound in the presence of phosphorus or carbon containing acid, ester or acid ester
Assignee: Dow Chemical Co
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Filing: 1973-06-21
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Granted: 1976-04-06
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Expires: 1993-06-21
Abstract
Abstract A process for the preparation of phenolic hydroxy ethers whereby an aromatic hydroxyl-containing compound is reacted with a vicinal epoxy-containing compound in the presence of a phosphonium salt of an acid, ester or acid ester of an element selected from carbon or phosphorus, and to precatalyzed epoxy resin compositions comprising an epoxy resin and a catalyst as defined above.
Inventors
- 👤 William O. Perry
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 08:14
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/68; C08G59/688; C08G59/40; C08G59/62; C08G59/621
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
163 words
In a process for preparing phenolic hydroxy ethers which comprises reacting a polyhydric phenol with a polyepoxide having more than one 1,2-epoxy group, the improvement comprising employing as the catalyst therefor, a phosphonium salt of an acid, ester or acid ester of the element carbon represented by the general formula ##EQU10## wherein R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of aliphatic hydrocarbon radicals containing from about 1 to about 20 carbon atoms, aromatic hydrocarbon radicals, alkyl substituted aromatic hydrocarbon radicals and radicals represented by the formula -R 5 Y wherein R 5 is an aliphatic hydrocarbon radical having from about 1 to about 20 carbon atoms and Y is a member selected from the group consisting of Cl, Br, I, and NO 2 , and wherein X is the anion portion of an acid, ester or acid ester of the element carbon and wherein m is the valence of the anion X.
Claim 2
Dependent Claim
163 words
In a process for preparing phenolic hydroxy ethers which comprises reacting a polyhydric phenol with a polyepoxide having more than one 1,2-epoxy group, the improvement comprising employing as the catalyst therefor, a phosphonium salt of an acid, ester or acid ester of the element carbon represented by the general formula ##EQU10## wherein R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of aliphatic hydrocarbon radicals containing from about 1 to about 20 carbon atoms, aromatic hydrocarbon radicals, alkyl substituted aromatic hydrocarbon radicals and radicals represented by the formula -R 5 Y wherein R 5 is an aliphatic hydrocarbon radical having from about 1 to about 20 carbon atoms and Y is a member selected from the group consisting of Cl, Br, I, and NO 2 , and wherein X is the anion portion of an acid, ester or acid ester of the element carbon and wherein m is the valence of the anion X.
Claim 3
Dependent Claim
154 words
The process of claim 1 wherein the catalyst is a phosphonium salt of an acid, ester or acid ester of the element carbon represented by general formula ##EQU11## wherein R 1 , R 2 , R 3 and R 4 are as defined in claim 1, m is the valence of the anion X 6 and has a value of 1 to 2, and X 6 is selected from the group represented by the formula ##EQU12## wherein R and R' are independently selected from the same group as R 1 , R 2 , R 3 and R 4 and additionally R can be selected from an alkenyl group having from about 1 to about 20 carbon atoms and R' can be an alkenylene group having from about 1 to about 20 carbon atoms, y has a value of zero or 1 and wherein n and n' have a value of zero or 1.
Claim 4
Dependent Claim
27 words
The process of claim 2 wherein each R 1 , R 2 , R 3 and R 4 is independently an aliphatic or an aromatic hydrocarbon group.
Claim 5
Dependent Claim
33 words
The process of claim 3 wherein X 6 is selected from the group represented by the formula ##EQU13## wherein R is an alkyl group containing from about 1 to about 20 carbon atoms.
Claim 6
Dependent Claim
11 words
The process of claim 4 wherein R is a methyl group.
Claim 7
Dependent Claim
14 words
The process of claim 5 wherein the catalyst is ethyltriphenylphosphonium acetate.sup.. acetic acid complex.
Claim 8
Dependent Claim
11 words
The process of claim 5 wherein the catalyst is ethyltriphenylphosphonium acetate.
Claim 9
Dependent Claim
30 words
The process of claim 4 wherein R 1 , R 2 , R 3 and R 4 are aliphatic hydrocarbon groups having from about 1 to about 20 carbon atoms.
Claim 10
Dependent Claim
11 words
The process of claim 8 wherein R is a methyl group.
Claim 11
Dependent Claim
14 words
The process of claim 9 wherein the catalyst is tetrabutylphosphonium acetate.sup.. acetic acid complex.
Claim 12
Dependent Claim
22 words
The process of claim 1 wherein the polyhydric phenol is a bisphenol and the polyepoxide is a diglycidyl ether of a bisphenol.
Claim 13
Dependent Claim
22 words
The process of claim 2 wherein the polyhydric phenol is a bisphenol and the polyepoxide is a diglycidyl ether of a bisphenol.
Claim 14
Dependent Claim
22 words
The process of claim 3 wherein the polyhydric phenol is a bisphenol and the polyepoxide is a diglycidyl ether of a bisphenol.
Claim 15
Dependent Claim
33 words
A precatalyzed epoxy resin composition comprising an epoxide resin containing an average of more than 1 vicinal epoxy group per molecule and a catalytic quantity of a catalyst as defined in claim 1.
Claim 16
Dependent Claim
33 words
A precatalyzed epoxy resin composition comprising an epoxide resin containing an average of more than 1 vicinal epoxy group per molecule and a catalytic quantity of a catalyst as defined in claim 2.
Claim 17
Dependent Claim
33 words
A precatalyzed epoxy resin composition comprising as epoxide resin containing an average of more than 1 vicinal epoxy group per molecule and a catalytic quantity of a catalyst as defined in claim 4.
Claim 18
Dependent Claim
33 words
A precatalyzed epoxy resin composition comprising an expoxide resin containing an average of more than 1 vicinal epoxy group per molecule and a catalytic quantity of a catalyst as defined in claim 10.
Claim 19
Dependent Claim
33 words
A precatalyzed epoxy resin composition comprising an epoxide resin containing an average of more than 1 vicinal epoxy group per molecule and a catalytic quantity of a catalyst as defined in claim 5.
Claim 20
Dependent Claim
74 words
A process for preparing high molecular weight resins which comprises reacting a polyepoxide having an epoxy equivalency greater than 1.0 with a polyhydric phenol in the presence of from about 0.001 percent to about 10 percent by weight of the reactants of a hydrocarbon phosphonium acetate-acetic acid complex of the general formula ##EQU14## wherein R 1 , R 2 , R 3 and R 4 are the same or different and represent hydrocarbon radicals.
Claim 21
Dependent Claim
74 words
A process for preparing high molecular weight resins which comprises reacting a polyepoxide having an epoxy equivalency greater than 1.0 with a polyhydric phenol in the presence of from about 0.001 percent to about 10 percent by weight of the reactants of a hydrocarbon phosphonium acetate-acetic acid complex of the general formula ##EQU14## wherein R 1 , R 2 , R 3 and R 4 are the same or different and represent hydrocarbon radicals.
Claim 22
Dependent Claim
82 words
A process for preparing high molecular weight resins which comprises reacting a polyepoxide having an epoxy equivalency greater than 1.0 with a polyhydric phenol in the presence of from about 0.001 percent to about 10 percent by weight of the reactants of a hydrocarbon phosphonium acetate catalyst of the general formula ##EQU15## wherein R 1 , R 2 , R 3 and R 4 are the same or different and represent hydrocarbon radicals, and n has a value of zero or one.
Claim 23
Dependent Claim
82 words
A process for preparing high molecular weight resins which comprises reacting a polyepoxide having an epoxy equivalency greater than 1.0 with a polyhydric phenol in the presence of from about 0.001 percent to about 10 percent by weight of the reactants of a hydrocarbon phosphonium acetate catalyst of the general formula ##EQU15## wherein R 1 , R 2 , R 3 and R 4 are the same or different and represent hydrocarbon radicals, and n has a value of zero or one.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-04-06 | 1979-10-06 | 1980-04-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-04-06 | 1983-10-06 | 1984-04-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-04-06 | 1987-10-06 | 1988-04-06 | $7700.00 | Window Closed / Lapsed |