Patent US4749728A successfully refreshed from Google Patents.
US4749728A
Expired / Lapsed
US
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Epoxy/nucleophile transesterification catalysts and thermoset coatings
Assignee: Akzo Nobel Paints LLC
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Filing: 1986-06-06
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Granted: 1988-06-07
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Expires: 2006-06-06
Abstract
Abstract A new transesterification catalyst comprises an epoxide and a non-acidic nucleophilic onium salt. Coating compositions having hydroxyl functional resin components and carboxylic ester components adapted for curing by transesterification following application to a substrate are formulated with in-situ formed cure catalyst comprising a non-acidic nucleophile and an epoxide-to-product coatings that readily cure by transesterification. Such coatings including polyesters, polyepoxides, and polyacrylates are useful in formulating high solids coatings and powder coatings having exceptional physical properties. Extremely low-temperature cure coatings were obtained by transesterifying mixtures of polyols and polymeric esters having multiple activated ester linkages having the structure <IMAGE> wherein R' is lower alkyl and Y is -OH and O-alkyl radicals. These coatings provide low-temperature cure coatings for paper, plastic, and wood in addition to metal substrates.
Inventors
- 👤 Gary P. Craun
- 👤 Kirk J. Abbey
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 02:38
CPC Classifications
C; C09; C09D; C09D167/00; C08; C08G; C08G59/00; C08G59/18; C08G59/68; C08G63/00; C08G63/78; C08G63/82; C08G63/87; C09D163/00; C09D201/00; C09D201/02; C09D201/06
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
130 words
A coating composition containing catalytic amount of transesterification catalyst, and adapted for curing by transesterification upon heating, the coating composition comprising: a polymeric binder containing hydroxyl functional groups and lower alkyl ester carboxylic ester functional groups adapted to transesterify in the presence of catalytic amounts of a transesterification catalyst, the transesterification catalyst comprising an epoxy compound containing oxirane functionality and a non-acidic nucleophilic compound substantially free of an active hydrogen and adapted to react with the oxirane functionality to form an in-situ transesterification cure of the polymeric binder, where said non-acidic nucleophilic compound is selected from an onium salt or a Lewis base, and said coating contains between 0.001 and 1 milliequivalents of said non-acidic nucleophilic compound and between 0.001 and 1 milliequivalents oxirane compound per gram of said coating.
Claim 2
Dependent Claim
130 words
A coating composition containing catalytic amount of transesterification catalyst, and adapted for curing by transesterification upon heating, the coating composition comprising: a polymeric binder containing hydroxyl functional groups and lower alkyl ester carboxylic ester functional groups adapted to transesterify in the presence of catalytic amounts of a transesterification catalyst, the transesterification catalyst comprising an epoxy compound containing oxirane functionality and a non-acidic nucleophilic compound substantially free of an active hydrogen and adapted to react with the oxirane functionality to form an in-situ transesterification cure of the polymeric binder, where said non-acidic nucleophilic compound is selected from an onium salt or a Lewis base, and said coating contains between 0.001 and 1 milliequivalents of said non-acidic nucleophilic compound and between 0.001 and 1 milliequivalents oxirane compound per gram of said coating.
Claim 3
Dependent Claim
16 words
The coating composition in claim 1 where the non-acidic nucleophilic compound is a quaternary ammonium salt.
Claim 4
Dependent Claim
16 words
The coating composition in claim 1 where the non-acidic nucleophilic compound is a quaternary phosphonium salt.
Claim 5
Dependent Claim
15 words
The coating composition in claim 1 where the non-acidic nucleophilc compound is tetrabutyl phosphonium acetate.
Claim 6
Dependent Claim
16 words
The coating composition in claim 1 where the non-acidic nucleophilic compound is ethyl triphenyl phosphonium acetate.
Claim 7
Dependent Claim
15 words
The coating composition in claim 1 where the non-acidic nucleophilic compound is a tertiary phosphine.
Claim 8
Dependent Claim
15 words
The coating composition in claim 1 where the non-acidic nucleophilic compound is a tertiary amine.
Claim 9
Dependent Claim
15 words
The coating composition in claim 1 where the non-acidic nucleophilic compound is a Lewis base.
Claim 10
Dependent Claim
25 words
The coating composition in claim 8 where the Lewis base contains an element selected from the group consisting of nitrogen, phosphorum, arsenic, antimony, and bismuth.
Claim 11
Dependent Claim
42 words
The coating composition in claim 1 where the epoxy compound is selected from the group consisting of 2-18 carbon alkylene oxide, aryl alkylene oxide, cycloaliphatic oxide, and phenolic glycidyl ether, where the epoxy compound has at least one oxirane group per molecule.
Claim 12
Dependent Claim
32 words
The coating composition in claim 1 where the epoxy compound is selected from an oligomer, a monomer, or a polymer, where the epoxy compound contains at least one oxirane group per molecule.
Claim 13
Dependent Claim
32 words
The coating composition in claim 1 where the polymeric binder is selected from the group consisting of a polyester, a polyacrylate, a polyepoxy, a polyamide, a polyurethane, a polycarbonate, or mixtures thereof.
Claim 14
Dependent Claim
28 words
The coating composition in claim 1 where the polymeric binder is solvent-free and comprises an oligomer polyester polyol and a lower alkyl diester of an alkyl dicarboxylic acid.
Claim 15
Dependent Claim
29 words
The coating composition in claim 1 where the polymeric binder comprises (a) a hydroxyl functional resin or polyol, and (b) a carboxylic acid ester or carboxylic ester functional resin.
Claim 16
Dependent Claim
31 words
The coating composition in claim 14 where the polymeric binder comprises (a) between 40% and 95% by weight polyester polyol, and (b) between 5% and 60% by weight lower alkyl diester.
Claim 17
Dependent Claim
18 words
The coating composition in claim 12 where the coating is a solvent based or solvent free acrylate polymer.
Claim 18
Dependent Claim
63 words
A low-temperature polyacrylate coating of claim 16 wherein the acrylate polymer monomer components comprise from about 5 to 40 weight percent basis total monomer of an activated ester monomer capable of reacting via transesterification, having the structure: ##STR7## wherein R is CH 2 ═CH-- or ##STR8## R' is lower alkyl; and Y is selected from the group consisting of --OH and O-alkyl radicals.
Claim 19
Dependent Claim
15 words
The coating of claim 17 wherein the activated ester monomer is methyl acrylamidoglycolate methyl ether.
Claim 20
Dependent Claim
68 words
A low-temperature coating composition adapted for curing by transesterification following application to a substrate which comprises (a) hydroxyl functional resin or polyol (b) carboxylic acid ester (c) an in-situ formed transesterification catalyst which comprises 0.001 to 1.0 milliequivalents epoxide and 0.001 to 1.0 milliequivalents non-acidic nucleophile or nucleophilic onium salt per gram of coating wherein said carboxylic ester is an activated diester derived from an alpha amino acid.
Claim 21
Dependent Claim
68 words
A low-temperature coating composition adapted for curing by transesterification following application to a substrate which comprises (a) hydroxyl functional resin or polyol (b) carboxylic acid ester (c) an in-situ formed transesterification catalyst which comprises 0.001 to 1.0 milliequivalents epoxide and 0.001 to 1.0 milliequivalents non-acidic nucleophile or nucleophilic onium salt per gram of coating wherein said carboxylic ester is an activated diester derived from an alpha amino acid.
References Cited (Backward Citations)
US4069055A
Cited
US4401774A
Cited
US4276406A
Cited
US4423168A
Cited
US4423169A
Cited
US4423167A
Cited
US4489182A
Cited
US4511447A
Cited
US4405662A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-06-07 | 1991-12-07 | 1992-06-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-06-07 | 1995-12-07 | 1996-06-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-06-07 | 1999-12-07 | 2000-06-07 | $7700.00 | Window Closed / Lapsed |