US4153776A
Expired / Lapsed
US
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Amide-modified urethane acrylate radiation curable compounds and coating compositions and methods of making same
Assignee: PPG Industries Inc
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Filing: 1978-03-28
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Granted: 1979-05-08
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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. The compounds comprise the reaction products of an amide-containing compound having at least one hydroxy functional group, a polyisocyanate and a polyfunctional compound having a hydroxy functional group reactive with an isocyanato group of the polyisocyanate, which polyfunctional compound provides an ethylenic functional group in the reaction product. Coating compositions containing these radiation curable reaction products cure at relatively high rates to form films having high abrasion resistance and improved tensile strength and elongation properties as compared to conventional urethane acrylate coating compositions.
Inventors
- 👤 Charles B. Friedlander
- 👤 Gerald W. Gruber
- 👤 Rostyslaw Dowbenko
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 19:46
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/038; C; C08; C08F; C08F299/00; C08F299/02; C08F299/06; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/67; C08G18/671; C08G18/672; Y; Y10; Y10S; Y10S525/00; Y10S525/92
Claims Analysis
Total Claims: 46
Claim 1
Independent Claim
80 words
Addition polymerizable compound having at least one amide group, at least one urethane group and at least one ethylenically unsaturated functional group comprising the reaction product of the components of (a) an amide-containing compound having at least one NCO-reactive hydroxy functional group; (b) a polyisocyanate; and (c) a polyfunctional compound containing at least one functional group reactive with an isocyanato group of said polyisocyanate and which polyfunctional compound provides at least one ethylenically unsaturated functional group in said reaction product.
Claim 2
Dependent Claim
80 words
Addition polymerizable compound having at least one amide group, at least one urethane group and at least one ethylenically unsaturated functional group comprising the reaction product of the components of (a) an amide-containing compound having at least one NCO-reactive hydroxy functional group; (b) a polyisocyanate; and (c) a polyfunctional compound containing at least one functional group reactive with an isocyanato group of said polyisocyanate and which polyfunctional compound provides at least one ethylenically unsaturated functional group in said reaction product.
Claim 3
Dependent Claim
105 words
The addition polymerizable compound of claim 1, wherein said amide-containing compound having at least one hydroxy functional group is selected from the group consisting of (a) a reaction product of a monocarboxylic acid and an aminoalcohol; (b) a reaction product of an ester of a carboxylic acid and an aminoalcohol; (c) a reaction product of a hydroxy carboxylic acid and a compound containing at least one amino nitrogen; (d) a reaction product of a lactone and ammonia or a compound containing at least one amino nitrogen; and (e) a reaction product of a lactide and ammonia or a compound containing at least one amino nitrogen.
Claim 4
Dependent Claim
22 words
The addition polymerizable compound of claim 1, wherein said amide-containing compound having at least one hydroxy functional group is a polyamide polyol.
Claim 5
Dependent Claim
27 words
The addition polymerizable compound of claim 2, wherein said monocarboxylic acid is selected from the group consisting of formic acid, acetic acid, propionic acid and benzoic acid.
Claim 6
Dependent Claim
30 words
The addition polymerizable compound of claim 2, wherein said ester of a carboxylic acid is selected from the group consisting of methyl formate, ethyl acetate, dimethyl adipate and methyl-2-ethyl hexanoate.
Claim 7
Dependent Claim
32 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
22 words
The addition polymerizable compound of claim 2, wherein said lactone is selected from the group consisting of γ-butyrolactone, γ-valerolactone, δ-valerolactone and ε-caprolactone.
Claim 9
Dependent Claim
37 words
The addition polymerizable compound of claim 2, wherein said compound containing at least one amino nitrogen is selected from the group consisting of aminoalcohol, aliphatic mono- or polyamine, aromatic mono- or polyamine and cyclic mono- or polyamine.
Claim 10
Dependent Claim
41 words
The addition polymerizable compound of claim 8, wherein said aminoalcohol that is reactable with one of said carboxylic acid, carboxylic acid ester, hydroxy carboxylic acid, lactone and lactide is selected from the group consisting of ethanolamine, diethanolamine, N-methylethanolamine and aminobenzyl alcohol.
Claim 11
Dependent Claim
28 words
The addition polymerizable compound of claim 8, wherein said aliphatic mono- or polyamine is selected from the group consisting of ethylenediamine, 1,2-propylenediamine, 1,3-propylenediamine, N,N-dimethylpropylenediamine, hexamethylenediamine and poly(alkyleneoxide diamines).
Claim 12
Dependent Claim
15 words
The addition polymerizable compound of claim 8, wherein said aromatic mono- or polyamine is benzylamine.
Claim 13
Dependent Claim
24 words
The addition polymerizable compound of claim 8, wherein said cyclic mono- or polyamine is selected from the group consisting of piperazine, piperidine and morpholine.
Claim 14
Dependent Claim
25 words
The addition polymerizable compound of claim 1, wherein said reaction product further comprises a moiety derived from the reaction of said polyisocyanate and a polyol.
Claim 15
Dependent Claim
27 words
The addition polymerizable compound of claim 13, wherein said polyol is selected from the group consisting of a polyester polyol, alkyl diol, alkyl triol and polyoxyalkylene polyol.
Claim 16
Dependent Claim
14 words
The addition polymerizable compound of claim 13, wherein said polyol is a poly(caprolactone) polyol.
Claim 17
Dependent Claim
24 words
The addition polymerizable compound of claim 13 or 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 18
Dependent Claim
24 words
The addition polymerizable compound of claim 1, wherein said polyfunctional compound is selected from the group consisting of acrylic acid and hydroxy-containing acrylic ester.
Claim 19
Dependent Claim
28 words
The addition polymerizable compound of claim 17, 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.
Claim 20
Dependent Claim
12 words
A coating composition containing addition polymerizable compound as defined in claim 1.
Claim 21
Dependent Claim
17 words
An article of manufacture having a cured film thereon made from the coating composition of claim 19.
Claim 22
Dependent Claim
38 words
The addition polymerizable compound of claim 2 wherein said amide-containing compound having at least one hydroxy functional group is a reaction product of γ-butyrolactone and ethanolamine, and wherein said reaction product of said γ-butyrolactone and ethanolamine comprises N-(2-hydroxyethyl)pyrrolidone.
Claim 23
Dependent Claim
57 words
A blend of the reaction product of claim 1 and the additional reaction product of (a) a polyol; (b) a polyisocyanate; and (c) a polyfunctional compound containing at least one functional group reactive with an isocyanato group of said polyisocyanate and which polyfunctional compound provides at least one ethylenically unsaturated functional group in said additional reaction product.
Claim 24
Independent Claim
70 words
A method for preparing an addition polymerizable compound comprising a reaction product, said method comprising reacting together the components of (a) an amide-containing compound having at least one NCO-reactive hydroxy functional group; (b) a polyisocyanate; and (c) a polyfunctional compound containing at least one functional group reactive with an isocyanato group of said polyisocyanate and which polyfunctional compound provides at least one ethylenically unsaturated functional group in said reaction product.
Claim 25
Independent Claim
70 words
A method for preparing an addition polymerizable compound comprising a reaction product, said method comprising reacting together the components of (a) an amide-containing compound having at least one NCO-reactive hydroxy functional group; (b) a polyisocyanate; and (c) a polyfunctional compound containing at least one functional group reactive with an isocyanato group of said polyisocyanate and which polyfunctional compound provides at least one ethylenically unsaturated functional group in said reaction product.
Claim 26
Dependent Claim
32 words
The method of claim 23, wherein said components and a polyol are reacted to provide in said reaction product a urethane moiety derived from the reaction of said polyisocyanate with said polyol.
Claim 27
Dependent Claim
102 words
The method of claim 23, wherein said reaction product is made by (a) forming a blend comprising (1) an NCO-terminated intermediate having at least one urethane group prepared from the reaction of said polyisocyanate and said amide-containing compound having at least one NCO-reactive hydroxy functional group; and (2) an NCO-terminated intermediate having at least one urethane group prepared from the reaction of a polyol and said polyisocyanate; (b) reacting said blend of NCO-terminated intermediates with said polyfunctional compound, to provide in said reaction product at least one amide group, at least one urethane group and at least one ethylenically unsaturated functional group.
Claim 28
Dependent Claim
48 words
The method of claim 25, wherein said reaction product is made by the steps of (a) adding a mixture of said amide-containing compound and said polyol to said polyisocyanate to form said blend comprising NCO-terminated intermediates; and (b) adding said polyfunctional compound to said blend of NCO-terminated intermediates.
Claim 29
Dependent Claim
26 words
The method of claim 26, wherein (a) said mixture is added gradually to said polyisocyanate; and (b) said polyfunctional compound is added gradually to said blend.
Claim 30
Dependent Claim
26 words
The method of claim 24 or 25, wherein said polyol is selected from the group consisting of polyester polyol, alkyl diol, alkyl triol and polyoxyalkylene polyol.
Claim 31
Dependent Claim
13 words
The method of claim 28, wherein said polyester polyol is a poly(caprolactone) polyol.
Claim 32
Dependent Claim
103 words
The method of claim 23, wherein said amide-containing compound having at least one hydroxy functional group is selected from the group consisting of (a) a reaction product of a monocarboxylic acid and an aminoalcohol; (b) a reaction product of an ester of a carboxylic acid and an aminoalcohol; (c) a reaction product of a hydroxy carboxylic acid and a compound containing at least one amino nitrogen; (d) a reaction product of a lactone and ammonia or a compound containing at least one amino nitrogen; and (e) a reaction product of a lactide and ammonia or a compound containing at least one amino nitrogen.
Claim 33
Dependent Claim
20 words
The method of claim 23, wherein said amide-containing compound having at least one hydroxy functional group is a polyamide polyol.
Claim 34
Dependent Claim
25 words
The method of claim 30, wherein said carboxylic acid is selected from the group consisting of formic acid, acetic acid, propionic acid and benzoic acid.
Claim 35
Dependent Claim
28 words
The method of claim 30, wherein said ester of a carboxylic acid is selected from the group consisting of methyl formate, ethyl acetate, methyl-2-ethyl hexanoate and dimethyl adipate.
Claim 36
Dependent Claim
30 words
The method of claim 30, 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 37
Dependent Claim
20 words
The method of claim 30, wherein said lactone is selected from the group consisting of γ-butyrolactone, γ-valerolactone, δ-valerolactone and ε-caprolactone.
Claim 38
Dependent Claim
35 words
The method of claim 30, wherein said compound containing at least one amino nitrogen is selected from the group consisting of aminoalcohol, aliphatic mono- or polyamine, aromatic mono- or polyamine and cyclic mono- or polyamine.
Claim 39
Dependent Claim
39 words
The method of claim 36, wherein said aminoalcohol that is reactable with one of said carboxylic acid, carboxylic acid ester, hydroxy carboxylic acid, lactone and lactide, is selected from the group consisting of ethanolamine, diethanolamine, N-methylethanolamine and aminobenzyl alcohol.
Claim 40
Dependent Claim
26 words
The method of claim 36, wherein said aliphatic mono- or polyamine is selected from the group consisting of ethylenediamine, 1,2-propylenediamine, 1,3-propylenediamine, N,N-dimethylpropylenediamine, hexamethylenediamine and poly(alkyleneoxide diamines).
Claim 41
Dependent Claim
13 words
The method of claim 36, wherein said aromatic mono- or polyamine is benzylamine.
Claim 42
Dependent Claim
22 words
The method of claim 36, wherein said cyclic mono- or polyamine is selected from the group consisting of piperazine, piperidine and morpholine.
Claim 43
Dependent Claim
23 words
The method of claim 23, 24 or 25, 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 44
Dependent Claim
24 words
The method of claim 23 or 25, wherein said polyfunctional compound is selected from the group consisting of acrylic acid and hydroxy-containing acrylic ester.
Claim 45
Dependent Claim
26 words
The method of claim 42, 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.
Claim 46
Dependent Claim
36 words
The method of claim 30 wherein said amide-containing compound having at least one hydroxy functional group is a reaction product of γ-butyrolactone and ethanolamine, and wherein said reaction product of said γ-butyrolactone and ethanolamine comprises N-(2-hydroxyethyl)pyrrolidone.
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) | 1982-05-07 | 1982-11-06 | 1983-05-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-05-07 | 1986-11-06 | 1987-05-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-05-07 | 1990-11-06 | 1991-05-08 | $7700.00 | Window Closed / Lapsed |