Patent US4354015A successfully refreshed from Google Patents.
US4354015A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Phosphonium bicarbonate catalysts for promoting reaction of epoxides with phenols
Assignee: Dow Chemical Co
•
Filing: 1981-10-21
•
Granted: 1982-10-12
•
Expires: 2001-10-21
Abstract
Abstract Tetrahydrocarbyl phosphonium bicarbonate salts are described which are unexpectedly effective as catalysts for promoting the reaction between (a) vicinal epoxides and (b) phenols. These catalysts are particularly useful in preparing high molecular weight epoxy resins by the advancement reaction of an epoxy resin with a polyhydric phenol.
Inventors
- 👤 George A. Doorakian
- 👤 Lawrence G. Duquette
- 👤 James L. Bertram
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 12:32
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/68; C08G59/688; C08G59/02; C08G59/04; C08G59/06; C08G59/066
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
129 words
In the process of preparing an epoxy resin by reacting (a) a compound bearing an average of more than one vicinal epoxide group per molecule with (b) a polyhydric phenol, the improvement comprising conducting the reaction in the presence of a compound represented by the formula I ##STR8## or a derivative thereof formed in situ, wherein R 1 -R 4 are each independently hydrocarbyl or inertly-substituted hydrocarbyl having up to 20 carbon atoms, the compound of formula I being present in an amount effective to prepare a resin having a weight average molecular weight at least 25 percent greater than that obtained with a like molar quantity of a R 1 R 2 R 3 R 4 P.sup.⊕ acetate salt or acetate/acetic acid complex under otherwise identical reaction conditions.
Claim 2
Dependent Claim
129 words
In the process of preparing an epoxy resin by reacting (a) a compound bearing an average of more than one vicinal epoxide group per molecule with (b) a polyhydric phenol, the improvement comprising conducting the reaction in the presence of a compound represented by the formula I ##STR8## or a derivative thereof formed in situ, wherein R 1 -R 4 are each independently hydrocarbyl or inertly-substituted hydrocarbyl having up to 20 carbon atoms, the compound of formula I being present in an amount effective to prepare a resin having a weight average molecular weight at least 25 percent greater than that obtained with a like molar quantity of a R 1 R 2 R 3 R 4 P.sup.⊕ acetate salt or acetate/acetic acid complex under otherwise identical reaction conditions.
Claim 3
Dependent Claim
66 words
The process described in claim 1 wherein the epoxy compound is represented by the formula ##STR9## wherein R' at each occurrence is independently selected from hydrogen, bromine and chlorine and wherein Z is selected from oxygen, sulfur, --SO--, --SO 2 --, bivalent hydrocarbon radicals containing up to about 10 carbon atoms, oxygen-, sulfur- and nitrogen-containing hydrocarbon radicals, and ##STR10## wherein R" is a bivalent hydrocarbon radical.
Claim 4
Dependent Claim
62 words
The process as described in claim 2 wherein the epoxide compound is reacted with a polyhydric phenol represented by the formula ##STR11## wherein each B independently is a hydrogen, halogen, hydrocarbyl, inertly-substituted hydrocarbyl or hydrocarbyloxy group, and Y is a single covalent bond, oxygen, sulfur, --CO--, --SO--, --SO 2 --, lower alkylene or alkylidene of from 1 to 6 carbon atoms, inclusive.
Claim 5
Dependent Claim
32 words
The process as described in claim 3 wherein the diglycidyl ether of bisphenol A is reacted with bisphenol A in the presence of a catalytic amount of triphenylethylphosphonium bicarbonate or tri-n-butylmethylphosphonium bicarbonate.
Claim 6
Dependent Claim
31 words
The process as described in claim 3 wherein the resulting resin has a weight average molecular weight at least 50 percent greater than that obtained with the corresponding phosphonium acetate salt.
Claim 7
Dependent Claim
22 words
The process as described in claim 1 wherein the polyhydric phenol is dihydric and the resulting polymer is linear or substantially linear.
Claim 8
Dependent Claim
31 words
The process as described in claim 6 wherein R 1 -R 4 each independently is phenyl or C 1 to C 12 alkyl or inertly-substituted C 1 to C 12 alkyl.
Claim 9
Dependent Claim
23 words
The process as described in claim 6 wherein R 1 -R 4 each independently is phenyl or C 1 to C 4 alkyl.
Claim 10
Dependent Claim
20 words
The process as described in claim 6 wherein R 1 -R 3 are each phenyl and R 4 is n-butyl.
Claim 11
Dependent Claim
25 words
The process as described in claim 6 wherein R 1 -R 3 are each phenyl or n-butyl and R 4 is methyl, ethyl or n-butyl.
Claim 12
Dependent Claim
20 words
The process as described in claim 6 wherein R 1 -R 3 are each phenyl and R 4 is ethyl.
Claim 13
Dependent Claim
20 words
The process as described in claim 6 wherein R 1 -R 3 are each n-butyl and R 4 is methyl.
Claim 14
Dependent Claim
38 words
The process as described in claim 4, which further comprises the addition of sufficient 2,2',6,6'-tetrabromobisphenol A as the advancement reaction approaches completion so as to react vicinal epoxy groups completely and increase the molecular weight of the product.
References Cited (Backward Citations)
CA893191A
Cited
US3193529A
Cited
US3306872A
Cited
US3477790A
Cited
US3547885A
Cited
US3660354A
Cited
US3637590A
Cited
US3948855A
Cited
US3784583A
Cited
US4048141A
Cited
US4302574A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-10-11 | 1986-04-12 | 1986-10-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-10-11 | 1990-04-12 | 1990-10-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-10-11 | 1994-04-12 | 1994-10-12 | $7700.00 | Window Closed / Lapsed |