US4078015A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Copolymerizable compositions and method of making the same
Assignee: UCB SA
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Filing: 1976-12-17
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Granted: 1978-03-07
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Expires: 1996-12-17
Abstract
Abstract Useful copolymerizable compositions include 10 to 50 parts by weight of (I) a polymerizable diurethane monomer having the general formula <IMAGE> wherein R1 is -H; or -CH3; R2 is -H; -CH3; or -C2H5; R3 is an organic radical constituting the residue of a mono-hydroxy compound R3OH having from one to twelve carbon atoms; and R4 is a divalent organic radical constituting the residue of an organic diisocyanate R4-(NCO)2 from which the two isocyanate radicals have been removed; AND 90 TO 50 PARTS BY WEIGHT OF (II) a polymerizable polyurethane monomer which is the reaction product of (a) an organic diisocyanate; (b) a beta-hydroxy alkyl ester of an acrylic acid; and (c) a polyol.
Inventors
- 👤 Robert H. Leitheiser
- 👤 John J. Szwarc
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 16:06
CPC Classifications
C; C08; C08F; C08F299/00; C08F299/02; C08F299/06; C08F20/00; C08F20/02; C08F20/10; C08F20/34; C08F20/36; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/67; C08G18/671; C08G18/672
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
136 words
A copolymerizable composition, substantially free of unreacted isocyanate groups, said composition being a liquid at temperatures in the range 50°-120° C and being a solid at room temperature, including (A) 10 to 50 parts by weight of a polymerizable acrylic diurethane monomer having the general formula ##STR6## wherein R 1 is --H or --CH 3 ; R 2 is --H, --CH 3 or --C 2 H 5 ; R 3 is an organic radical constituting the residue of a lower alkyl alcohol R 3 OH; and R 4 is a divalent organic radical ##STR7## and (B) 90 to 50 parts by weight of a polymerizable polyacrylic polyurethane monomer which is the reaction product of (a) an organic diisocyanate R 4 -(NCO) 2 ; (b) a beta-hydroxy alkyl ester of an acrylic acid; and (c) a diol.
Claim 2
Dependent Claim
136 words
A copolymerizable composition, substantially free of unreacted isocyanate groups, said composition being a liquid at temperatures in the range 50°-120° C and being a solid at room temperature, including (A) 10 to 50 parts by weight of a polymerizable acrylic diurethane monomer having the general formula ##STR6## wherein R 1 is --H or --CH 3 ; R 2 is --H, --CH 3 or --C 2 H 5 ; R 3 is an organic radical constituting the residue of a lower alkyl alcohol R 3 OH; and R 4 is a divalent organic radical ##STR7## and (B) 90 to 50 parts by weight of a polymerizable polyacrylic polyurethane monomer which is the reaction product of (a) an organic diisocyanate R 4 -(NCO) 2 ; (b) a beta-hydroxy alkyl ester of an acrylic acid; and (c) a diol.
Claim 3
Dependent Claim
18 words
The composition of claim 1 including 0.1 to 3.0 percent by weight of a sensitizer for actinic radiation.
Claim 4
Dependent Claim
18 words
The composition of claim 1 wherein the said diol is a polyester of adipic acid and diethylene glycol.
Claim 5
Dependent Claim
13 words
The composition of claim 1 wherein the said diol is a polycaprolactone diol.
Claim 6
Dependent Claim
41 words
The composition of claim 1 wherein the said polyacrylic-polyurethane monomer is the reaction product of (a) dicyclohexyl-methane diisocyanate; (b) a polyester of adipic acid and diethylene glycol; (c) beta-hydroxy ethyl acrylate; and R 1 is --H; and R 2 is --H.
Claim 7
Independent Claim
109 words
The method of preparing a copolymerizable mixture comprising: (a) reacting organic diisocyanate, mol-for-mol with beta-hydroxy alkyl ester of an acrylic acid; (b) reacting a polyol with an excess of the reaction product of STEP (a) to produce a mixture, substantially free of unreacted --OH grups containing the reaction product of the said polyol and the said reaction product of STEP (a) along with unreacted product of STEP (a); (c) reacting the mixture resulting from STEP (b) with sufficient lower alkyl alcohol to combine with the unreacted --NCO groups in the mixture; and (d) recovering a copolymerizable mixture substantially free of unreacted --NCO groups containing acrylate-diurethane monomers and polyurethane-polyacrylate monomers.
Claim 8
Independent Claim
109 words
The method of preparing a copolymerizable mixture comprising: (a) reacting organic diisocyanate, mol-for-mol with beta-hydroxy alkyl ester of an acrylic acid; (b) reacting a polyol with an excess of the reaction product of STEP (a) to produce a mixture, substantially free of unreacted --OH grups containing the reaction product of the said polyol and the said reaction product of STEP (a) along with unreacted product of STEP (a); (c) reacting the mixture resulting from STEP (b) with sufficient lower alkyl alcohol to combine with the unreacted --NCO groups in the mixture; and (d) recovering a copolymerizable mixture substantially free of unreacted --NCO groups containing acrylate-diurethane monomers and polyurethane-polyacrylate monomers.
Claim 9
Dependent Claim
80 words
The method of claim 6 wherein (A) the said organic diisocyanate is selected from the class consisting of diphenyl methane diisocyanate and dicyclohexyl methane diisocyanate; (B) the said beta-hydroxy alkyl ester is selected from the class consisting of (i) beta-hydroxy ethyl acrylate or methacrylate and (ii) beta-hydroxy propyl acrylate or methacrylate; (C) the said diol is selected from the class consisting of (i) polycaprolactone ester diol and (ii) hydroxy-terminated polyesters of polyhydric alcohols and polycarboxylic acids or polycarboxylic acid anhydrides.
Claim 10
Dependent Claim
21 words
The method of claim 7 including the additional STEP (e) of adding a sensitizer for actinic radiation to the copolymerizable mixture.
Claim 11
Dependent Claim
28 words
The method of claim 8 including the additional STEP (f) of forming the liquid copolymerizable mixture into flat sheets and recovering solid, tack-free sheets of a polymerizable composition.
Claim 12
Dependent Claim
17 words
The composition of claim 1 wherein the said diol is an alkylene oxide adduct of a glycol.
Claim 13
Dependent Claim
12 words
The composition of claim 10 wherein the said diol is polypropylene glycol.
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) | 1981-03-06 | 1981-09-05 | 1982-03-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-03-06 | 1985-09-05 | 1986-03-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-03-06 | 1989-09-05 | 1990-03-07 | $7700.00 | Window Closed / Lapsed |