US5519093A
Expired / Lapsed
US
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Synthesis of amine functional co-and terpolymers
Assignee: University of Pittsburgh
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Filing: 1994-05-11
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Granted: 1996-05-21
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Expires: 2014-05-11
Abstract
Abstract Amine functional polymers are prepared by polymerization of vinylamides with vinyl ester monomers. The resultant polymers are hydrolyzed under acid conditions and subsequently at least partially basified to the free-base amine. Byproduct salts are removed by precipitation or by extraction into an immiscible phase. The polymers made by this method are crosslinkable through reaction of the amine groups and are useful in high performance coatings, adhesives, binders and the like.
Inventors
- 👤 Robert K. Pinschmidt, Jr.
- 👤 Khalil Yacoub
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 08:18
CPC Classifications
C; C08; C08F; C08F8/00; C08F8/12; C08F2800/00; C08F2800/10; C08F2800/20; C08F2810/00; C08F2810/50
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
82 words
A process for producing amine functional hydrophobic polymers which can be crosslinked through reaction of amine groups, said process comprising: polymerizing a vinylamide with one or more vinyl ester monomers selected from the group consisting of vinyl sec-alkyl carboxylates, vinyl tert-alkyl carboxylates and mixtures thereof to form a co- or terpolymer, hydrolyzing said co- or terpolymer under acid conditions, subsequently at least partially basifying said polymer to the free-base amine and removing byproduct salts and recovering said amine functional co- or terpolymer.
Claim 2
Dependent Claim
82 words
A process for producing amine functional hydrophobic polymers which can be crosslinked through reaction of amine groups, said process comprising: polymerizing a vinylamide with one or more vinyl ester monomers selected from the group consisting of vinyl sec-alkyl carboxylates, vinyl tert-alkyl carboxylates and mixtures thereof to form a co- or terpolymer, hydrolyzing said co- or terpolymer under acid conditions, subsequently at least partially basifying said polymer to the free-base amine and removing byproduct salts and recovering said amine functional co- or terpolymer.
Claim 3
Dependent Claim
12 words
A process in accordance with claim 1 wherein said vinylamide is N-vinylformamide.
Claim 4
Dependent Claim
20 words
A process in accordance with claim 1 wherein said vinyl ester is a vinyl,2-ethyl hexanoate or a neo-acid vinyl ester.
Claim 5
Dependent Claim
21 words
A process in accordance with claim 1 wherein said co- or terpolymer has a molecular weight from 7,000 to 60,000 (Mw).
Claim 6
Dependent Claim
17 words
A process in accordance with claim 1 wherein said hydrolysis is carried out in an alcohol-containing solvent.
Claim 7
Dependent Claim
14 words
A process in accordance with claim 1 wherein said polymer is basified using CaO.
Claim 8
Dependent Claim
20 words
A process in accordance with claim 1 wherein said vinylamide is polymerized with said vinyl esters by free radical polymerization.
Claim 9
Dependent Claim
27 words
A process in accordance with claim 1 wherein said vinylamide and said vinyl esters are polymerized via a suspension bead process in water as the continuous phase.
Claim 10
Dependent Claim
23 words
A process in accordance with claim 1 wherein an oxidant is added to the polymer solution prior to carrying out the acid hydrolysis.
Claim 11
Dependent Claim
16 words
A process in accordance with claim 1 wherein said oxidant is t-butyl hydroperoxide or hydrogen peroxide.
Claim 12
Dependent Claim
24 words
A process in accordance with claim 1 wherein said hydrolysis is carried out using para-toluene sulfonic acid or methanesulfonic acid in a primary alcohol.
Claim 13
Dependent Claim
28 words
A process in accordance with claim 1 wherein said hydrolysis is carried out using an acid selected from the group consisting of sulfuric, methanesulfonic, hydrochloric and nitric acids.
Claim 14
Dependent Claim
20 words
A process in accordance with claim 1 wherein said vinylamide is polymerized with said vinyl ester monomer via suspension polymerization.
Claim 15
Dependent Claim
22 words
A process in accordance with claim 1 wherein said vinylamide is polymerized with said vinyl ester monomer via solution or emulsion polymerization.
Claim 16
Dependent Claim
25 words
A process in accordance with claim 1 wherein said byproduct salts are removed by precipitation, extraction into an immiscible phase, or high temperature hydrolysis/formate disproportionation.
Claim 17
Dependent Claim
19 words
A process in accordance with claim 13 wherein poly-N-vinylformamide is used as a suspending agent in the suspension polymerization.
Claim 18
Dependent Claim
21 words
A process in accordance with claim 16 wherein poly-N-vinylformamide is used in an amount from 0.01 to 1.0% based on monomers.
References Cited (Backward Citations)
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US4774285A
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US4880497A
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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) | 1999-05-21 | 1999-11-20 | 2000-05-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2003-05-21 | 2003-11-20 | 2004-05-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2007-05-21 | 2007-11-20 | 2008-05-21 | $7700.00 | Window Closed / Lapsed |