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US4760168A
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Preparation of alkyl acrylamidoglycolates and their alkyl ethers
Assignee: Wyeth Holdings LLC
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Filing: 1987-02-20
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Granted: 1988-07-26
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Expires: 2007-02-20
Abstract
Abstract Reaction of an acrylamide with an alkyl glyoxylate or an alkyl glyoxylate hemiacetal provides an alkyl acrylamidoglycolate which can readily be alkylated to provide the alkyl ether thereof.
Inventors
- 👤 Peter J. Schirmann
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 16:05
CPC Classifications
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Claims Analysis
Total Claims: 3
Claim 1
Independent Claim
139 words
A process for preparing an alkyl acrylamidoglycolate alkyl ether in solid form wherein the alkyl groups in the ester and ether functionalities are the same, which comprises reacting an acrylamide with an alkyl glyoxylate hemiacetal in essentially equal molar proportions at a temperature in the range of about 50° C. to about 90° C. in the presence of a polymerization inhibitor to yield an alkyl acrylamidoglycolate, reacting said alkyl acrylamidoglycolate in the presence of an etherification catalyst at reflux temperature with an excess of an alcohol selected from the group consisting of aliphatic and cycloaliphatic alcohols of 1-6 carbon atoms and 1,2-dihydroxy alcohols of 2-6 carbon atoms whose alkyl group is the same as the alkyl group in the ester functionality of said alkyl acrylamidoglycolate to yield said alkyl acrylamidoglycolate alkyl ether and removing the excess alcohol by distillation.
Claim 2
Dependent Claim
139 words
A process for preparing an alkyl acrylamidoglycolate alkyl ether in solid form wherein the alkyl groups in the ester and ether functionalities are the same, which comprises reacting an acrylamide with an alkyl glyoxylate hemiacetal in essentially equal molar proportions at a temperature in the range of about 50° C. to about 90° C. in the presence of a polymerization inhibitor to yield an alkyl acrylamidoglycolate, reacting said alkyl acrylamidoglycolate in the presence of an etherification catalyst at reflux temperature with an excess of an alcohol selected from the group consisting of aliphatic and cycloaliphatic alcohols of 1-6 carbon atoms and 1,2-dihydroxy alcohols of 2-6 carbon atoms whose alkyl group is the same as the alkyl group in the ester functionality of said alkyl acrylamidoglycolate to yield said alkyl acrylamidoglycolate alkyl ether and removing the excess alcohol by distillation.
Claim 3
Dependent Claim
26 words
the process of claim 1 wherein the alkyl glyoxylate hemiacetal is selected from methyl glyoxylate methyl hemiacetal, ethyl glyoxylate ethyl hemiacetal and butyl glyoxylate butyl hemiacetal.
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) | 1991-07-26 | 1992-01-25 | 1992-07-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-07-26 | 1996-01-25 | 1996-07-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-07-26 | 2000-01-25 | 2000-07-26 | $7700.00 | Window Closed / Lapsed |