US3687897A
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Preparation of oxazolidinones by reacting an isocyanate, or isothiocyanate with an epoxide in the presence of a phosphonium halide acid, ester, or acid ester of the element c
Assignee: Dow Chemical Co
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Filing: 1970-06-22
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Granted: 1972-08-29
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Expires: 1990-06-22
Abstract
Abstract Oxazolidinones are prepared by reacting an organic isocyanate such as toluene diisocyanate with a vicinal epoxide such as the diglycidyl ether of p,p''-isopropylidine diphenol in the presence of a phosphonium catalyst such as tetrabutyl phosphonium bromide. The oxazolidinone compounds prepared herein are known to be useful as chemical intermediates and in the manufacture of resins and plastics.
Inventors
- 👤 James A Clarke
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 18:54
CPC Classifications
C; C07; C07D; C07D263/00; C07D263/02; C07D263/08; C07D263/16; C07D263/18; C07D263/20; C08; C08G; C08G18/00; C08G18/003; C08G18/06; C08G18/08; C08G18/16; C08G18/166; C08G18/168; C08G59/00; C08G59/18; C08G59/40; C08G59/4007; C08G59/4014; C08G59/4028; C08G65/00; C08G65/02; C08G65/26; C08G65/2618
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
18 words
The process of claim 1 wherein the NCO: or NCS:epoxide ratio is from about 0.1:1 to about 1:0.1.
Claim 2
Dependent Claim
28 words
The process of claim 2 wherein the isocyanate or isothiocyanate is a diisocyanate or diisothiocyanate and the vicinal epoxide is a polyepoxide having a functionality greater than 1.
Claim 3
Dependent Claim
149 words
A process for preparing oxazolidinone containing compounds, said process comprising reacting a vicinal epoxide containing compound with a carbamate formed by the reaction of an isocyanate or isothiocyanate containing compound with a primary or secondary aliphatic alcohol in an isocyanate or isothiocyanate to OH ratio of about 1:1, said epoxide-carbamate reaction being conducted in the presence of a catalytic amount of a phosphonium catalyst, represented by the general formula, wherein R1, R2 and R3 are independently selected from the group consisting of hydrogen, aliphatic hydrocarbon radicals containing from about one to about 20 carbon atoms, R4 is selected from the same group as R1, R2 and R3 and aromatic hydrocarbon radicals and alkyl substituted aromatic hydrocarbon radicals and wherein X is Cl, Br, I or 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 4
Dependent Claim
22 words
The process of claim 4 wherein the ratio of carbamate groups to vicinal epoxide groups is from about 0.1:1 to about 1:0.1.
Claim 5
Dependent Claim
22 words
The process of claim 5 wherein the ratio of carbamate group to vicinal epoxide groups is from about 0.1:1 to about 0.5:1.
Claim 6
Dependent Claim
33 words
The process of claim 6 wherein the isocyanate employed in the preparation of the carbamate is a diisocyanate and the vicinal epoxide containing compound has an average epoxide functionality greater than about 1.
Claim 7
Dependent Claim
20 words
The process of claim 7 wherein the vicinal epoxide containing compound is an epoxy resin represented by the general formula
Claim 8
Dependent Claim
17 words
The process of claim 1 wherein the catalyst is a phosphonium compound represented by the general formula,
Claim 9
Dependent Claim
17 words
The process of claim 4 wherein the catalyst is a phosphonium compound represented by the general formula,
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) | 1975-08-29 | 1976-02-28 | 1976-08-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1979-08-29 | 1980-02-28 | 1980-08-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1983-08-29 | 1984-02-28 | 1984-08-29 | $7700.00 | Window Closed / Lapsed |