Patent US4133723A successfully refreshed from Google Patents.
US4133723A
Expired / Lapsed
US
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Actinic radiation-curable formulations from the reaction product of organic isocyanate, poly(alkylene oxide) polyol and an unsaturated addition-polymerizable monomeric compound having a single isocyanate-reactive hydrogen group
Assignee: Lord Corp
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Filing: 1978-01-03
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Granted: 1979-01-09
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Expires: 1998-01-03
Abstract
Abstract Energy-curable compositions which can be cured in the presence of air by exposure to actinic radiation contain at least one unsaturated urethane oligomer, said oligomer comprising the reaction product of at least one poly(alkylene oxide) polyol, at least one polyisocyanate, and at least one unsaturated active hydrogen-containing compound.
Inventors
- 👤 Dennis D. Howard
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 22:27
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/48; C08F; C08F299/00; C08F299/02; C08F299/06; C08G18/42; C08G18/4244; C08G18/4247; C08G18/4252; C08G18/67; C08G18/671
Claims Analysis
Total Claims: 34
Claim 1
Independent Claim
222 words
A coating composition comprising (A) at least one unsaturated urethane resin comprising the reaction product of (i) at least one organic isocyanate compound having at least two isocyanate groups; (ii) at least one poly(alkylene oxide) polyol, said polyol having from 1 to 9 carbon atoms in the alkylene group separating each pair of oxygen atoms, and (iii) at least one unsaturated addition-polymerizable monomeric compound having a single isocyanate-reactive active hydrogen group; there being present an excess of isocyanate compound with respect to the hydroxyl groups of said poly(alkylene oxide) polyol; said unsaturated addition-polymerizable monomeric compound having a single isocyanate-reactive active hydrogen group being present in an amount sufficient to provide at least one molar equivalent of active hydrogen group with respect to isocyanate reactivity; B) a reactive diluent system comprising at least one unsaturated addition-polymerizable monomeric compound which is copolymerizable with said unsaturated urethane resin; the amount of unsaturated urethane resin being in the range from about 30 to about 90 weight percent, based on total weight of unsaturated urethane resin and reactive diluent system; (C) At least one aromatic ketone or aromatic aldehyde photosensitizer which promotes photopolymerization through bimolecular photochemical reactions of the energy donor type or hydrogen abstraction type; and (D) At least one aromatic ketone photoinitiator which generates a radical pair by way of unimolecular homolysis resulting from photoexcitation.
Claim 2
Dependent Claim
222 words
A coating composition comprising (A) at least one unsaturated urethane resin comprising the reaction product of (i) at least one organic isocyanate compound having at least two isocyanate groups; (ii) at least one poly(alkylene oxide) polyol, said polyol having from 1 to 9 carbon atoms in the alkylene group separating each pair of oxygen atoms, and (iii) at least one unsaturated addition-polymerizable monomeric compound having a single isocyanate-reactive active hydrogen group; there being present an excess of isocyanate compound with respect to the hydroxyl groups of said poly(alkylene oxide) polyol; said unsaturated addition-polymerizable monomeric compound having a single isocyanate-reactive active hydrogen group being present in an amount sufficient to provide at least one molar equivalent of active hydrogen group with respect to isocyanate reactivity; B) a reactive diluent system comprising at least one unsaturated addition-polymerizable monomeric compound which is copolymerizable with said unsaturated urethane resin; the amount of unsaturated urethane resin being in the range from about 30 to about 90 weight percent, based on total weight of unsaturated urethane resin and reactive diluent system; (C) At least one aromatic ketone or aromatic aldehyde photosensitizer which promotes photopolymerization through bimolecular photochemical reactions of the energy donor type or hydrogen abstraction type; and (D) At least one aromatic ketone photoinitiator which generates a radical pair by way of unimolecular homolysis resulting from photoexcitation.
Claim 3
Dependent Claim
20 words
A coating composition according to claim 1 wherein at least one of said poly(alkylene oxide) polyols is poly)tetramethylene oxide) glycol.
Claim 4
Dependent Claim
37 words
A coating composition according to claim 1 wherein said isocyanate compound is present in an amount sufficient to provide an NCO:OH ratio of at least 2.3:1, with respect to the hydroxyl groups of said polyalkylene ether polyol.
Claim 5
Dependent Claim
68 words
A coating composition according to claim 3 wherein said photosensitizer is present in an amount in the range from about 0.01 to about 50 parts by weight, and said photoinitiator is present in an amount in the range from about 0.01 to about 10 parts by weight, said parts by weight being per 100 parts by combined weight of said unsaturated urethane resin and said reactive diluent system.
Claim 6
Dependent Claim
20 words
A coating composition according to claim 4 wherein at least one of said poly(alkylene oxide) polyols is poly(tetramethylene oxide) glycol.
Claim 7
Dependent Claim
19 words
A coating composition according to claim 5 wherein said photosensitizer is benzophenone and said photoinitiator comprises benzoin isobutyl ether.
Claim 8
Dependent Claim
82 words
A coating composition according to claim 1 containing from about 0.01 to about 5 parts by weight, per 100 parts by combined weight of said urethane resin and said reactive diluent system, of at least one thiol selected from the group consisting of monothiols and polythiols, said polythiols having a molecular weight in the range from about 95 to about 20,000 and having the general formula R.sup.9 (SH).sub.m, wherein R 9 is a polyvalent organic moiety and m is at least 2.
Claim 9
Dependent Claim
20 words
A coating composition according to claim 7 wherein at least one of said poly(alkylene oxide) polyols is poly(tetramethylene oxide) glycol.
Claim 10
Dependent Claim
36 words
A coating composition according to claim 7 wherein such isocyanate compound is present in an amount sufficient to provide an NCO:OH ratio of at least 2.3:1, with respect to hydroxyl groups of such poly(alkylene oxide) polyols.
Claim 11
Dependent Claim
68 words
A coating composition according to claim 9 wherein said photosensitizer is present in an amount in the range from about 0.01 to about 50 parts by weight, and said photoinitiator is present in an amount in the range from about 0.01 to about 10 parts by weight, said parts by weight being per 100 parts by combined weight of said unsaturated urethane resin and said reactive diluent system.
Claim 12
Dependent Claim
20 words
A coating composition according to claim 10 wherein at least one of said poly(alkylene oxide) polyols is poly(tetramethylene oxide) glycol.
Claim 13
Dependent Claim
26 words
A coating composition according to claim 11 wherein said photosensitizer is benzophenone, said photoinitiator is benzoin isobutyl ether, and said thiol compound is pentaerythritol tetrakis (β-mercaptopropionate).
Claim 14
Dependent Claim
54 words
a coating composition according to claim 12 wherein said diluent system contains at least one unsaturated addition-polymerizable monofunctional monomeric compound selected from the group consisting of esters having the general formula ##STR6## wherein R o is hydrogen or methyl and R is an aliphatic or cycloaliphatic group having from 4 to 18 carbon atoms.
Claim 15
Dependent Claim
20 words
A coating composition according to claim 13 wherein at least one of said poly(alkylene oxide) polyols is poly(tetramethylene oxide) glycol.
Claim 16
Dependent Claim
26 words
A coating composition according to claim 14 wherein said photosensitizer is benzophenone, said photoinitiator is benzoin isobutyl ether, and said thiol compound is pentaerythritol tetrakis (β-mercaptopropionate).
Claim 17
Dependent Claim
148 words
A coating composition according to claim 1 wherein said unsaturated urethane resin comprises the reaction product of (A) at least one isocyanate-functional prepolymer, said prepolymer comprising the reaction product of (a) at least one organic isocyanate compound having at least two isocyanate groups; and (b) at least one poly(alkylene oxide) polyol, said polyol having from 1 to 9 carbon atoms in the alkylene group separating each pair of oxygen atoms; the amount of such isocyanate compound being sufficient to provide an excess of isocyanate groups with respect to hydroxyl groups of such poly(alkylene oxide) polyol; and (B) at least one unsaturated addition-polymerizable monomeric compound having a single isocyanate-reactive active hydrogen group; the amount of such unsaturated addition-polymerizable monomeric compound having a single isocyanate-reactive active hydrogen group being sufficient to provide at least one molar equivalent of active hydrogen group with respect to the isocyanate groups of such prepolymer.
Claim 18
Dependent Claim
20 words
A coating composition according to claim 16 wherein at least one of said poly(alkylene oxide) polyols is poly(tetramethylene oxide) glycol.
Claim 19
Dependent Claim
37 words
A coating composition according to claim 16 wherein said isocyanate compound is present in an amount sufficient to provide an NCO:OH ratio of at least 2.3:1, with respect to the hydroxyl groups of said poly(alkylene oxide) polyol.
Claim 20
Dependent Claim
68 words
A coating composition according to claim 18 wherein said photosensitizer is present in an amount in the range from about 0.01 to about 50 parts by weight, and said photoinitiator is present in an amount in the range from about 0.01 to about 10 parts by weight, said parts by weight being per 100 parts by combined weight of said unsaturated urethane resin and said reactive diluent system.
Claim 21
Dependent Claim
20 words
A coating composition according to claim 19 wherein at least one of said poly(alkylene oxide) polyols is poly(tetramethylene oxide) glycol.
Claim 22
Dependent Claim
19 words
A coating composition according to claim 20 wherein said photosensitizer is benzophenone and said photoinitiator is benzoin isotutyl ether.
Claim 23
Dependent Claim
81 words
A composition according to claim 16 containing from about 0.01 to about 5 parts by weight, per 100 parts by combined weight of said urethane resin and said reactive diluent system of at least one thiol selected from the group consisting of monothiols and polythiols, said polythiols having a molecular weight in the range from about 95 to about 20,000 and having the general formula R.sup.9 (SH).sub.m, wherein R 9 is a polyvalent organic moiety and m is at least 2.
Claim 24
Dependent Claim
20 words
A coating composition according to claim 22 wherein at least one of said poly(alkylene oxide) polyols is poly(tetramethylene oxide) glycol.
Claim 25
Dependent Claim
37 words
A coating composition according to claim 22 wherein such isocyanate compound is present in an amount sufficient to provide an NCO:OH ratio of at least 2.3:1, with respect to the hydroxyl groups of such poly(alkylene oxide) polyols.
Claim 26
Dependent Claim
68 words
A coating composition according to claim 24 wherein said photosensitizer is present in an amount in the range from about 0.01 to about 50 parts by weight and said photoinitiator is present in an amount in the range from about 0.01 to about 10 parts by weight, said parts by weight being per 100 parts by combined weight of said unsaturated urethane resin and said reactive diluent system.
Claim 27
Dependent Claim
20 words
A coating composition according to claim 25 wherein at least one of said poly(alkylene oxide) polyols is poly(tetramethylene oxide) glycol.
Claim 28
Dependent Claim
25 words
A coating composition according to claim 26 wherein said photosensitizer is benzophenone, said photoinitiator is benzoin isobutyl ether, and said thiol is pentaerythritol tetrakis (β-mercaptopropionate).
Claim 29
Dependent Claim
54 words
A coating composition according to claim 24 wherein said diluent system contains at least one unsaturated addition-polymerizable monofunctional monomeric compound selected from the group consisting of esters having the general formula ##STR7## wherein R o is hydrogen or methyl and R is an aliphatic or cycloaliphatic group having from 4 to 18 carbon atoms.
Claim 30
Dependent Claim
20 words
A coating composition according to claim 28 wherein at least one of said poly(alkylene oxide) polyols is poly(tetramethylene oxide) glycol.
Claim 31
Dependent Claim
25 words
A coating composition according to claim 29 wherein said photosensitizer is benzophenone, said photoinitiator is benzoin butyl ether, and said thiol is pentaerythritol tetrakis (β-mercaptopropionate).
Claim 32
Dependent Claim
25 words
A coating composition according to claim 30 wherein said poly(tetramethylene oxide) glycol has a molecular weight in the range from about 250 to about 4000.
Claim 33
Dependent Claim
46 words
A method for coating a substrate comprising applying to said substrate a coating composition according to claim 1, and exposing such coated substrate to actinic radiation in the presence of oxygen for a period of time sufficient to cure said coating to a hard mar-resistant surface.
Claim 34
Dependent Claim
5 words
The product of claim 32.
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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) | 1982-01-08 | 1982-07-10 | 1983-01-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-01-08 | 1986-07-10 | 1987-01-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-01-08 | 1990-07-10 | 1991-01-09 | $7700.00 | Window Closed / Lapsed |