Patent US2223348A successfully refreshed from Google Patents.
US4187366A
Expired / Lapsed
US
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Amide-modified urethane acrylate radiation curable compounds derived from condensation reaction products of carboxyl and isocyanato groups
Assignee: PPG Industries Inc
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Filing: 1978-03-28
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Granted: 1980-02-05
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Expires: 1998-03-28
Abstract
Abstract Radiation curable compounds are disclosed comprising an amide moiety, a urethane moiety and an ethylenically unsaturated functional group, typically an acrylate functional group. This class of amide urethane acrylate compounds is characterized in having an amide moiety formed by the condensation reaction between a compound containing one or more carboxylic acid groups and an isocyanato-containing compound. Coating compositions containing one or more of these amide urethane acrylate compounds radiation polymerize at relatively high rates to provide protective and decorative films having improved wear resistance and flexibility.
Inventors
- 👤 Charles B. Friedlander
- 👤 John C. McMullen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 23:48
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/30; C08G18/34; C08G18/67; C08G18/671
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
110 words
Addition polymerizable compound comprising the reaction product of (a) carboxylic acid containing at least one carboxyl functional group; (b) polyisocyanate; and (c) polyfunctional compound containing at least one hydroxyl group which is reactive with an isocyanato group of said polyisocyanate and which polyfunctional compound provides at least one ethylenic functional group in said reaction product; wherein said addition polymerizable compound contains (d) at least one amide group formed by reaction of a carboxyl group of said carboxylic acid with an isocyanato group of said polyisocyanate; and (e) at least one urethane group formed by reaction of a hydroxyl group of said polyfunctional compound with an isocyanate group of said polyisocyanate.
Claim 2
Dependent Claim
110 words
Addition polymerizable compound comprising the reaction product of (a) carboxylic acid containing at least one carboxyl functional group; (b) polyisocyanate; and (c) polyfunctional compound containing at least one hydroxyl group which is reactive with an isocyanato group of said polyisocyanate and which polyfunctional compound provides at least one ethylenic functional group in said reaction product; wherein said addition polymerizable compound contains (d) at least one amide group formed by reaction of a carboxyl group of said carboxylic acid with an isocyanato group of said polyisocyanate; and (e) at least one urethane group formed by reaction of a hydroxyl group of said polyfunctional compound with an isocyanate group of said polyisocyanate.
Claim 3
Dependent Claim
30 words
The addition polymerizable compound of claim 1 wherein said carboxylic acid is selected from the group consisting of saturated monocarboxylic acid, saturated polycarboxylic acid, unsaturated polycarboxylic acid and hydroxycarboxylic acid.
Claim 4
Dependent Claim
28 words
The addition polymerizable compound of claim 2 wherein said saturated monocarboxylic acid is selected from the group consisting of acetic acid, propionic acid, 2-ethylhexanoic acid and benzoic acid.
Claim 5
Dependent Claim
26 words
The addition polymerizable compound of claim 2 wherein said saturated polycarboxylic acid is selected from the group consisting of adipic acid, azelaic acid and dodecanedioic acid.
Claim 6
Dependent Claim
24 words
The addition polymerizable compound of claim 2 wherein said unsaturated polycarboxylic acid is selected from the group consisting of fumaric acid and itaconic acid.
Claim 7
Dependent Claim
31 words
The addition polymerizable compound of claim 2 wherein said hydroxy-carboxylic acid is hydroxyacetic acid, 2,2-bis(hydroxymethyl)propionic acid or an aromatic hydroxy acid prepared from the reaction of phthalic anhydride and diethylene glycol.
Claim 8
Dependent Claim
32 words
The addition polymerizable compound of claim 1 comprising the reaction product of said components and a polyol selected from the group consisting of polyester polyol, alkyl diol, alkyl triol and polyether polyol.
Claim 9
Dependent Claim
15 words
The addition polymerizable compound of claim 7 wherein said polyester polyol is a poly(caprolactone) polyol.
Claim 10
Dependent Claim
22 words
The addition polymerizable compound of claim 1 wherein said polyisocyanate is selected from the group consisting of 1-isocyanatomethyl-5-isocyanato-1,3,3-trimethylcyclohexane, toluene diisocyanate and bis(4-isocyanatocyclohexyl)methane.
Claim 11
Dependent Claim
15 words
The addition polymerizable compound of claim 1 wherein said polyfunctional compound is hydroxyl-containing acrylic ester.
Claim 12
Dependent Claim
28 words
The addition polymerizable compound of claim 10 wherein said hydroxyl-containing acrylic ester is selected from the group consisting of 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 2-hydroxyethyl methacrylate and 2-hydroxypropyl methacrylate.
Claim 13
Dependent Claim
12 words
A coating composition containing addition polymerizable compound as defined in claim 1.
Claim 14
Dependent Claim
17 words
An article of manufacture having a cured film thereon made from the coating composition of claim 12.
Claim 15
Independent Claim
114 words
A method for preparing an addition polymerizable compound comprising reacting (a) carboxylic acid containing at least one carboxyl functional group; (b) polyisocyanate; and (c) polyfunctional compound containing at least one hydroxyl group which is reactive with an isocyanato group of said polyisocyanate and which polyfunctional compound provides at least one ethylenically unsaturated functional group in said addition polymerizable compound; wherein said addition polymerizable compound contains (d) at least one amide group formed by reaction of a carboxyl group of said carboxylic acid with an isocyanato group of said polyisocyanate; and (e) at least one urethane group formed by reaction of a hydroxyl group of said polyfunctional compound with an isocyanate group of said polyisocyanate.
Claim 16
Independent Claim
114 words
A method for preparing an addition polymerizable compound comprising reacting (a) carboxylic acid containing at least one carboxyl functional group; (b) polyisocyanate; and (c) polyfunctional compound containing at least one hydroxyl group which is reactive with an isocyanato group of said polyisocyanate and which polyfunctional compound provides at least one ethylenically unsaturated functional group in said addition polymerizable compound; wherein said addition polymerizable compound contains (d) at least one amide group formed by reaction of a carboxyl group of said carboxylic acid with an isocyanato group of said polyisocyanate; and (e) at least one urethane group formed by reaction of a hydroxyl group of said polyfunctional compound with an isocyanate group of said polyisocyanate.
Claim 17
Dependent Claim
38 words
The method of claim 14 wherein said addition polymerizable compound is made by (a) reacting said carboxylic acid with said polyisocyanate to form an NCO-terminated amide intermediate; and (b) reacting said polyfunctional compound with said NCO-terminated amide intermediate.
Claim 18
Dependent Claim
37 words
The method of claim 14 wherein said addition polymerizable compound is made by reacting together said components and a polyol selected from the group consisting of polyester polyol, alkyl diol, alkyl triol, polyether polyol and polyoxyalkylene polyol.
Claim 19
Dependent Claim
54 words
The method of claim 16 wherein said addition polymerizable compound is made by the steps of (a) adding a mixture of said carboxylic acid and said polyol to said polyisocyanate to form a blend comprising amide-containing NCO-terminated intermediate and urethane-containing NCO-terminated intermediate; and (b) adding said polyfunctional compound to said blend of NCO-terminated intermediates.
Claim 20
Independent Claim
33 words
The method of claims 15 or 17 wherein (a) said carboxylic acid or said mixture is added gradually to said polyisocyanate; and (b) said polyfunctional compound is added gradually to said NCO-terminated intermediates.
Claim 21
Dependent Claim
12 words
The method of claim 16 wherein said polyester polyol is poly(oxybutylene glycol).
Claim 22
Dependent Claim
28 words
The method of claim 14 wherein said carboxylic acid is selected from the group consisting of saturated monocarboxylic acid, saturated polycarboxylic acid, unsaturated polycarboxylic acid and hydroxy-carboxylic acid.
Claim 23
Dependent Claim
26 words
The method of claim 20 wherein said saturated monocarboxylic acid is selected from the group consisting of acetic acid, propionic acid, 2-ethylhexanoic acid and benzoic acid.
Claim 24
Dependent Claim
24 words
The method of claim 20 wherein said saturated polycarboxylic acid is selected from the group consisting of adipic acid, azelaic acid and dodecanedioic acid.
Claim 25
Dependent Claim
22 words
The method of claim 20 wherein said unsaturated polycarboxylic acid is selected from the group consisting of fumaric acid and itaconic acid.
Claim 26
Dependent Claim
29 words
The method of claim 20 wherein said hydroxy-carboxylic acid is hydroxyacetic acid, 2,2-bis(hydroxymethyl)propionic acid or an aromatic hydroxy acid prepared from the reaction of phthalic anhydride and diethylene glycol.
Claim 27
Dependent Claim
20 words
The method of claim 14 wherein said polyisocyanate is selected from the group consisting of 1-isocyanatomethyl-5-isocyanato-1,3,3-trimethylcyclohexane, toluene diisocyanate and bis(4-isocyanatocyclohexyl)methane.
Claim 28
Dependent Claim
13 words
The method of claim 14 wherein said polyfunctional compound is hydroxy-containing acrylic ester.
Claim 29
Dependent Claim
26 words
The method of claim 26 wherein said hydroxy-containing acrylic ester is selected from the group consisting of 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 2-hydroxyethyl methacrylate and 2-hydroxypropyl methacrylate.
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) | 1983-02-04 | 1983-08-06 | 1984-02-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-02-04 | 1987-08-06 | 1988-02-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-02-04 | 1991-08-06 | 1992-02-05 | $7700.00 | Window Closed / Lapsed |