Patent US4072770A successfully refreshed from Google Patents.
US4072770A
Expired / Lapsed
US
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U.V. curable poly(ester-urethane) polyacrylate polymers and wet look coatings therefrom
Assignee: Lilly Industries Inc
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Filing: 1976-05-11
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Granted: 1978-02-07
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Expires: 1996-05-11
Abstract
Abstract Polyester-urethane polymers, prepared from the reaction of specific molar ratios of diisocyanates with specific mixtures of polyesterdiols, glycols, triols and tetraols, and having 4-10 reactive isocyanate groups are further reacted with hydroxyalkyl acrylates through the free isocyanate functionality to provide oligomers having from about 4-10 acrylates units per each mole unit of polyurethane chain. Such polymers when crosslinked under ultraviolet radiation in the presence of photosensitizers, specific reactive monofunctional acrylate solvents and multifunctional acrylate cross-linking agents cure without air inhibition to yield superior "wet look" finishes especially useful for coating metal, wood and floor tile.
Inventors
- 👤 Vincent W. Ting
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 16:00
CPC Classifications
C; C08; C08F; C08F299/00; C08F299/02; C08F299/06; B; B05; B05D; B05D5/00; B05D5/06; B05D5/061; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/65; C08G18/66; C08G18/6633; C08G18/6637; C08G18/664; C08G18/6644; C08G18/67; C08G18/671; C08G18/672; B05D3/00; B05D3/06; B05D3/061; B05D3/065; B05D3/067; Y; Y10; Y10S; Y10S430/00; Y10S430/1053; Y10S430/1055; Y10S430/114; Y10S430/124; Y10S525/00; Y10S525/92
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
90 words
A poly(ester-urethane) polyacrylate polymer comprising the product obtained by reacting a polyurethane intermediate having 4 to 10 terminally-positioned reactive isocyanate groups with 4 to 10 molar equivalents of a hydroxy (lower) acrylate or methacrylate said intermediate resulting from the reaction of 1 to 7 moles of a polyester diol having a molecular weight in the range of 500 to 12,000; 2 to 8 moles of a monomer polyol having 3 to 12 carbon atoms and at least 3 reactive hydroxyl groups; and 6 to 24 moles of an organic diisocyanate.
Claim 2
Dependent Claim
90 words
A poly(ester-urethane) polyacrylate polymer comprising the product obtained by reacting a polyurethane intermediate having 4 to 10 terminally-positioned reactive isocyanate groups with 4 to 10 molar equivalents of a hydroxy (lower) acrylate or methacrylate said intermediate resulting from the reaction of 1 to 7 moles of a polyester diol having a molecular weight in the range of 500 to 12,000; 2 to 8 moles of a monomer polyol having 3 to 12 carbon atoms and at least 3 reactive hydroxyl groups; and 6 to 24 moles of an organic diisocyanate.
Claim 3
Dependent Claim
48 words
The polymer of claim 1 wherein the polyester diol comprises the reaction product of adipic acid and a diol selected from the group consisting of 1,6-hexanediol, 1,4-cyclohexane dimethanol and hydrogenated bisphenol A; the monomer polyol is trimethylolpropane; the diiocyanate is isiphorone diisocynate; and the hydroxyacrylate is hydroxyethyl acrylate.
Claim 4
Dependent Claim
13 words
The composition of claim 2 wherein the molar ratio of polyester:trimethyolpropane:dissocyanate:hydroxyacrylate is 2:3:9:5.
Claim 5
Dependent Claim
52 words
A U.V. curable composition comprising on a weight percent basis 30 to 70 percent of a polyurethane polymer of claim 1; 10 to 40 percent of a monofunctional acrylate monomer; 5 to 50 percent of multifunctional acrylate cross-linking agent and 3 to 5 percent of a photosensitizer, said composition totaling 100 percent.
Claim 6
Dependent Claim
41 words
The composition of claim 4 wherein the polyurethane intermediate comprises the reaction product of 2 moles of a polyester diol, 3 moles of monomer polyol and 9 moles of organic diisocyanate, said intermediate being further reacted with 5 moles of hydroxyalkylacrylate.
Claim 7
Dependent Claim
45 words
The composition of claim 4 wherein the polyurethane intermediate is prepared using 1 mole of polyesterdiol having a molecular weight of 1250, 2 moles of trimethylol propane and 6 moles of isophorone diisocyanate, said intermediate being further reacted with 4 moles of a hydroxyalkyl acrylate.
Claim 8
Dependent Claim
20 words
The composition of claim 4 wherein the photosensitizer is selected from the group consisting of benzophenone, diethoxyacetophenone and mixtures thereof.
Claim 9
Dependent Claim
23 words
The composition of claim 5 wherein the photosensitizer is a mixture comprising 1 to 3 parts benzophenone and 1 part of diethoxy acetophenone.
Claim 10
Dependent Claim
132 words
A process for imparting a wet look coating to a substrate which comprises: (a) forming a radiation curable composition comprising on a weight percent basis: (i) 30 to 70 percent of a polyurethane polymer of claim 1; (ii) 10 to 40 percent of a monofunctional acrylate monomer; (iii) 5 to 50 percent of a multifunctional acrylate cross-linking agent; and (iv) 3 to 5 percent of a photosensitizer said composition totaling 100 percent; (b) applying said mixture as a 0.1 to 10 mil thick coating to a substrate selected from the group consisting of flat stock metal, wood, fiberboard and floor tile; and (c) curing said coating substrate in air at ambient temperature by passing the substrate at a rate of from 10 to 1000 foot/minute through an effective field of ultraviolet radiation.
Claim 11
Dependent Claim
89 words
The process of claim 9 wherein the polyurethane oligomer comprises the reaction product of: (a) a polyester diol formed from adipic acid and a diol selected from the group consisting of 1,6-hexanediol, 1,4-cyclohexane dimethanol, hydrogenated bisphenol A, and propylene glycol; (b) a monomer polyol selected from the group consisting a trimethylol propane, trimethylol ethane, glycerine, polycaprolactone triols, pentaerythritol and mixtures thereof; (c) isophorone diisocyanate, and (d) hydroxyacrylate selected from the group consisting of 2-hydroxyethylacrylate, 2-hydroxy-3-chloropropyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropylacrylate and mixtures thereof; wherein the ratio of a:b:c:d is 2:3:9:5.
Claim 12
Dependent Claim
31 words
The process of claim 10 wherein the polyesterdiol is a propylene glycol adipate, the monomer triol is trimethylol propane, the organic diisocyanate is isophorone diisocyanate and the hydroxyacrylate is 2-hydroxyethyl acrylate.
Claim 13
Dependent Claim
22 words
The process of claim 9 wherein the acrylate monomer is selected from the group consisting of 2-phenoxyethyl acrylate, isobornyl acrylate and benzylacrylate.
Claim 14
Dependent Claim
30 words
The process of claim 9 wherein the multifunctional cross-linking agent is selected from the group consisting of melamine acrylate; pentaerythritol triacrylate, trimethylolpropane triacrylate, epoxidized soybean oil acrylate and neopentylglycol diacrylate.
Claim 15
Dependent Claim
19 words
The process of claim 13 wherein the monoacrylate monomer is isobornyl acrylate and the cross-linking agent is melamine acrylate.
Claim 16
Dependent Claim
12 words
The process of claim 12 wherein the substrate is aluminum flat stock.
References Cited (Backward Citations)
US3673140A
Cited
US3954714A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-02-06 | 1981-08-08 | 1982-02-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-02-06 | 1985-08-08 | 1986-02-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-02-06 | 1989-08-08 | 1990-02-07 | $7700.00 | Window Closed / Lapsed |