US4607084A
Expired / Lapsed
US
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Radiation curable acrylated polyurethane oligomer compositions
Assignee: Hi Tek Polymers Inc
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Filing: 1985-12-16
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Granted: 1986-08-19
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Expires: 2005-12-16
Abstract
Abstract Radiation cured compositions having improved abrasion resistance and cure response are made from blends of the reaction product of a diisocyanate, a hydroxyalkyl acrylate and a polyether diol with the reaction product of a diisocyanate, a hydroxyalkyl acrylate and a polyether triol wherein the average acrylate functionality of the blends is from about 2.4 to about 2.6. Such cured compositions are useful as coatings for various substrates.
Inventors
- 👤 William J. Morris, deceased
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 02:34
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/81; C08G18/8141; C08G18/815; C08G18/8158; C08G18/8175; C08G18/28; C08G18/40; C08G18/48; C08G18/4804; C08G18/4812; C08G18/67; C08G18/671; C08G18/672; C08G18/72; C08G18/73; C08G18/74; C08G18/75; C08G18/758; C09; C09D; C09D175/00; C09D175/04; C09D175/14; C09D175/16
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
205 words
A radiation curable composition which comprises acrylated polyurethane oligomers which are the reaction product of (a) an organic diisocyanate, (b) a polyether diol, and (c) a hydroxyalkyl acrylate or methacrylate blended with the reaction product of (d) an organic diisocyanate, (e) a polyether triol, and (f) a hydroxyalkyl acrylate or methacrylate wherein the organic diisocyanate, (a) and (d), is an aliphatic or cycloaliphatic diisocyanate; wherein the polyether diol, (b), is a dihydroxy terminated polyalkylene oxide which contains 2 to 4 carbon atoms in each alkylene group and which has a molecular weight of about 800 to about 2000; wherein the polyether triol, (e), is a trihydroxy terminated polyalkylene oxide which contains 2 to 3 carbon atoms in each alkylene group and which has a molecular weight of about 300 to about 750; wherein the alkyl group of the hydroxyalkyl acrylate or methacrylate contains 2 or 3 carbon atoms; wherein (b) and (e) are in such molar ratios that the resultant composition has an average acrylate or methacrylate functionality of about 2.4 to about 2.6; wherein 1 mole of diisocyanate is reacted per hydroxyl group of the polyether diol and triol; and wherein 1 mole of hydroxyalkyl acrylate or methacrylate is reacted per mole of diisocyanate.
Claim 2
Dependent Claim
205 words
A radiation curable composition which comprises acrylated polyurethane oligomers which are the reaction product of (a) an organic diisocyanate, (b) a polyether diol, and (c) a hydroxyalkyl acrylate or methacrylate blended with the reaction product of (d) an organic diisocyanate, (e) a polyether triol, and (f) a hydroxyalkyl acrylate or methacrylate wherein the organic diisocyanate, (a) and (d), is an aliphatic or cycloaliphatic diisocyanate; wherein the polyether diol, (b), is a dihydroxy terminated polyalkylene oxide which contains 2 to 4 carbon atoms in each alkylene group and which has a molecular weight of about 800 to about 2000; wherein the polyether triol, (e), is a trihydroxy terminated polyalkylene oxide which contains 2 to 3 carbon atoms in each alkylene group and which has a molecular weight of about 300 to about 750; wherein the alkyl group of the hydroxyalkyl acrylate or methacrylate contains 2 or 3 carbon atoms; wherein (b) and (e) are in such molar ratios that the resultant composition has an average acrylate or methacrylate functionality of about 2.4 to about 2.6; wherein 1 mole of diisocyanate is reacted per hydroxyl group of the polyether diol and triol; and wherein 1 mole of hydroxyalkyl acrylate or methacrylate is reacted per mole of diisocyanate.
Claim 3
Dependent Claim
40 words
The composition of claim 1 wherein the polyether diol and the polyether triol are preblended in a molar ratio of 0.9:1 to 1.1:1 and the reactions of the diisocyanate and the hydroxyalkyl acrylate or methacrylate are conducted with the blend.
Claim 4
Dependent Claim
14 words
The composition of claim 1 wherein the average acrylate or methacrylate functionality is 2.5.
Claim 5
Dependent Claim
21 words
The composition of claim 2 wherein the polyether diol and the polyether triol are preblended in a molar ratio of 1:1.
Claim 6
Dependent Claim
10 words
The composition of claim 1 wherein the diisocyanate is 4,4'-methylene-bis(cyclohexylisocyanate).
Claim 7
Dependent Claim
11 words
The composition of claim 1 wherein the diisocyanate is isophorone diisocyanate.
Claim 8
Dependent Claim
24 words
The composition of claim 1 wherein the polyether diol is a dihydroxy terminated polyalkylene oxide which contains 4 carbon atoms in each alkylene group.
Claim 9
Dependent Claim
13 words
The composition of claim 7 wherein the polyether diol is derived from tetrahydrofuran.
Claim 10
Dependent Claim
27 words
The composition of claim 1 wherein the polyether triol has a molecular weight of about 400 and the polyether diol has a molecular weight of about 1000.
Claim 11
Dependent Claim
12 words
The composition of claim 1 wherein the hydroxyalkyl acrylate is hydroxyethyl acrylate.
Claim 12
Dependent Claim
12 words
The composition of claim 1 wherein the hydroxyalkyl acrylate is hydroxypropyl acrylate.
Claim 13
Independent Claim
216 words
A method for providing improved abrasion resistance and cure response to radiation cured compositions which comprises using as the radiation curable composition the reaction product of (a) an organic diisocyanate, (b) a polyether diol, and (c) a hydroxyalkyl acrylate or methacrylate blended with the reaction product of (d) an organic diisocyanate, (e) a polyether triol, and (f) a hydroxyalkyl acrylate or methacrylate wherein the organic diisocyanate, (a) and (d), is an aliphatic or cycloaliphatic diisocyanate; wherein the polyether diol, (b), is a dihydroxy terminated polyalkylene oxide which contains 2 to 4 carbon atoms in each alkylene group and which has a molecular weight of about 800 to about 2000; wherein the polyether triol, (e), is a trihydroxy terminated polyalkylene oxide which contains 2 to 3 carbon atoms in each alkylene group and which has a molecular weight of about 300 to about 750; wherein the alkyl group of the hydroxyalkyl acrylate or methacrylate contains 2 or 3 carbon atoms; wherein (b) and (e) are in such molar ratios that the resultant composition has an average acrylate or methacrylate functionality of about 2.4 to about 2.6; wherein 1 mole of diisocyanate is reacted per hydroxyl group of the polyether diol and triol; and wherein 1 mole of hydroxyalkyl acrylate or methacrylate is reacted per mole of diisocyanate.
Claim 14
Independent Claim
216 words
A method for providing improved abrasion resistance and cure response to radiation cured compositions which comprises using as the radiation curable composition the reaction product of (a) an organic diisocyanate, (b) a polyether diol, and (c) a hydroxyalkyl acrylate or methacrylate blended with the reaction product of (d) an organic diisocyanate, (e) a polyether triol, and (f) a hydroxyalkyl acrylate or methacrylate wherein the organic diisocyanate, (a) and (d), is an aliphatic or cycloaliphatic diisocyanate; wherein the polyether diol, (b), is a dihydroxy terminated polyalkylene oxide which contains 2 to 4 carbon atoms in each alkylene group and which has a molecular weight of about 800 to about 2000; wherein the polyether triol, (e), is a trihydroxy terminated polyalkylene oxide which contains 2 to 3 carbon atoms in each alkylene group and which has a molecular weight of about 300 to about 750; wherein the alkyl group of the hydroxyalkyl acrylate or methacrylate contains 2 or 3 carbon atoms; wherein (b) and (e) are in such molar ratios that the resultant composition has an average acrylate or methacrylate functionality of about 2.4 to about 2.6; wherein 1 mole of diisocyanate is reacted per hydroxyl group of the polyether diol and triol; and wherein 1 mole of hydroxyalkyl acrylate or methacrylate is reacted per mole of diisocyanate.
Claim 15
Dependent Claim
40 words
The method of claim 12 wherein the polyether diol and the polyether triol are preblended in a molar ratio of 0.9:1 to 1.1:1 and the reactions of the diisocyanate and the hydroxyalkyl acrylate or methacrylate are conducted with the blend.
Claim 16
Dependent Claim
14 words
The method of claim 12 wherein the average acrylate or methacrylate functionality is 2.5.
Claim 17
Dependent Claim
21 words
The method of claim 13 wherein the polyether diol and the polyether triol are preblended in a molar ratio of 1:1.
Claim 18
Dependent Claim
10 words
The method of claim 12 wherein the diisocyanate is 4,4'-methylene-bis(cyclohexylisocyanate).
Claim 19
Dependent Claim
11 words
The method of claim 12 wherein the diisocyanate is isophorone diisocyanate.
Claim 20
Dependent Claim
23 words
The method claim 12 wherein the polyether diol is a dihydroxy terminated polyalkylene oxide which contains 4 carbon atoms in each alkylene group.
Claim 21
Dependent Claim
13 words
The method of claim 18 wherein the polyether diol is derived from tetrahydrofuran.
Claim 22
Dependent Claim
27 words
The method of claim 12 wherein the polyether triol has a molecular weight of about 400 and the polyether diol has a molecular weight of about 1000.
Claim 23
Dependent Claim
12 words
The method of claim 12 wherein the hydroxyalkyl acrylate is hydroxyethyl acrylate.
Claim 24
Dependent Claim
12 words
The method of claim 12 wherein the hydroxyalkyl acrylate is hydroxypropyl acrylate.
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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) | 1989-08-18 | 1990-02-17 | 1990-08-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-08-18 | 1994-02-17 | 1994-08-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-08-18 | 1998-02-17 | 1998-08-19 | $7700.00 | Window Closed / Lapsed |