US5091489A
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Oligo (2-alkenyl azlactones)
Assignee: 3M Co
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Filing: 1991-07-24
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Granted: 1992-02-25
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Expires: 2011-07-24
Abstract
Abstract This invention provides novel azlactone-functional oligomers of 2-alkenyl azlactones in which oligomerization has occurred predominantly via the 2-alkenyl group. Oligomerization of the 2-alkenyl group provides oligomers having 2 to 15 mer units with predominantly carbon-carbon backbone segments. Oligomerized in this fashion, the novel compositions possess azlactone groups which can be reacted with nucleophiles in the normal ring-opening sense. The oligomers are prepared by a novel process in which both Lewis and Bronsted acidic catalysts are effective. The reactive oligomers find utility as crosslinking agents for polymers containing azlactone-reactable nucleophilic groups.
Inventors
- 👤 Steven M. Heilmann
- 👤 Dean M. Moren
- 👤 Jerald K. Rasmussen
- 👤 Larry R. Krepski
- 👤 Sadanand V. Pathre
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 04:16
CPC Classifications
C; C07; C07D; C07D263/00; C07D263/02; C07D263/30; C07D263/34; C07D263/36; C07D263/42
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
43 words
A method comprising the steps: oligomerizing at least one 2-alkenyl 4,4-disubstituted azlactone in the presence of a catalytically effective amount of an acid to provide an oligomer having 2 to 15 units which are at least 30 mol % 2-alkenyl group polymerized units.
Claim 2
Independent Claim
43 words
A method comprising the steps: oligomerizing at least one 2-alkenyl 4,4-disubstituted azlactone in the presence of a catalytically effective amount of an acid to provide an oligomer having 2 to 15 units which are at least 30 mol % 2-alkenyl group polymerized units.
Claim 3
Dependent Claim
15 words
The method according to claim 1 wherein said acid is a Bronsted or Lewis acid.
Claim 4
Dependent Claim
17 words
The method according to claim 2 wherein said Bronsted acid has a pKa of less than 1.2.
Claim 5
Dependent Claim
38 words
The method according to claim 2 wherein said Bronsted acid is selected from the group consisting of: sulfuric acid, hydrogen chloride, hydrogen bromide, hydrogen iodide, trifluoroacetic acid, trichloroacetic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, perchloric acid, and ethanesulfonic acid.
Claim 6
Dependent Claim
29 words
The method according to claim 2 wherein said Lewis acid is selected from the group consisting of: aluminum chloride, zinc chloride, boron trifluoride, antimony pentachloride, titanium tetrachloride and iodine.
Claim 7
Dependent Claim
21 words
The method according to claim 1 wherein said 2-alkenyl azlactone is selected from the group consisting of: 2-vinyl-4,4-dimethyl-2-oxazolin-5-one, 2-isopropenyl-4,4-dimethyl-2-oxazolin-5-one, 2-vinyl-4-ethyl-4-methyl-2-oxazolin-5-one, 2-vinyl-4,4-dimethyl-1,3-oxazin-6-one.
Claim 8
Dependent Claim
13 words
The method according to claim 6 wherein said 2-alkenyl azlactone is 2-vinyl-4,4-dimethyl azlactone.
References Cited (Backward Citations)
US4304705A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1995-02-24 | 1995-08-26 | 1996-02-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-02-24 | 1999-08-26 | 2000-02-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-02-24 | 2003-08-26 | 2004-02-25 | $7700.00 | Window Closed / Lapsed |