US5183831A
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US
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Radiation curable composition with high temperature oil resistance
Assignee: Novartis Corp
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Filing: 1991-08-22
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Granted: 1993-02-02
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Expires: 2011-08-22
Abstract
Abstract The present invention relates to a radiation curable composition with high temperature oil resistance comprising (1) a(meth)acrylated urethane component comprising (a) the reaction product of hydroxyethyl(meth)acrylate and a monomeric or polymeric aromatic isocyanate, (b) hydroxyethyl(meth)acrylate, and optionally (c) a(meth)acylated prepolymer of a monomeric of polymeric aromatic isocyanate and at least one polycaprolactone polyol with a functionality≧2 and a molecular weight in the range of about 500 to about 3,000 or (d) a(meth)acrylated prepolymer of a monomeric or polymeric aromatic isocyanate and at least one polyether polyol with a functionality≧2 and a molecular weight in the range of about 90 to about 7,000, or a mixture of (c) and (d); (2) an aromatic multifunctional epoxy (meth)acrylate having a molecular weight of less than about 1000; (3) at least one free radical polymerizable monomer; and (4) a free radical photoinitiator, which composition exhibits at 25° C. (i) a Tg greater than about 45° C., (ii) an elongation of greater than about 3%, (iii) a tensile strength of greater than about 1300 psi and (iv) a shear storage modulus of greater than about 4300 psi.
Inventors
- 👤 Richard A. Bielat
- 👤 Kieran F. Drain
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 07:49
CPC Classifications
C; C08; C08F; C08F290/00; C08F290/08; C08F290/14; C08F290/147; C08F290/144; C09; C09D; C09D4/00
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
139 words
A radiation curable composition with high temperature oil resistance comprising (1) a (meth)acrylated urethane component comprising (a) the reaction product of hydroxyethyl(meth)acrylate and a monomeric or polymeric aromatic isocyanate, (b) hydroxyethyl(meth)acrylate; and (c) a (meth)acrylated prepolymer of a monomeric or polymeric aromatic isocyanate and at least one polycaprolactone polyol with a functionality>2 and a molecular weight in the range of about 500 to about 3,000; (2) an aromatic multifunctional epoxy (meth)acrylate having a molecular weight of less than about 1000; (3) at least one free radical polymerizable monomer; and (4) a free radical photoinitiator, which composition exhibits at 25° C.: : (i) a Tg greater than about 45° C., (ii) an elongation of greater than about 3%, (iii) a tensile strength of greater than about 1300 psi and (iv) a shear storage modulus of greater than about 4300 psi.
Claim 2
Dependent Claim
139 words
A radiation curable composition with high temperature oil resistance comprising (1) a (meth)acrylated urethane component comprising (a) the reaction product of hydroxyethyl(meth)acrylate and a monomeric or polymeric aromatic isocyanate, (b) hydroxyethyl(meth)acrylate; and (c) a (meth)acrylated prepolymer of a monomeric or polymeric aromatic isocyanate and at least one polycaprolactone polyol with a functionality>2 and a molecular weight in the range of about 500 to about 3,000; (2) an aromatic multifunctional epoxy (meth)acrylate having a molecular weight of less than about 1000; (3) at least one free radical polymerizable monomer; and (4) a free radical photoinitiator, which composition exhibits at 25° C.: : (i) a Tg greater than about 45° C., (ii) an elongation of greater than about 3%, (iii) a tensile strength of greater than about 1300 psi and (iv) a shear storage modulus of greater than about 4300 psi.
Claim 3
Dependent Claim
32 words
A radition curable composition according to claim 1 wherein said aromatic isocyanate is selected from the group consisting of methylene bis(4-isocyanato benzene), toluene diisocyanate, 3,3'-toluidine-4,4'-diisocyanate, 3,3'-dimethyl-diphenylmethane-4,4'-diisocyanate, 1,5-diisocyanato-naphthalene, 1,4-diisocyanato-benzene and 1,4- and 1,3-di(isocyanato-dimethyl)-benzene.
Claim 4
Dependent Claim
17 words
A radiation curable composition according to claim 1 wherein said aromatic isocyanate is monomeric methylene bis(4-isocyanato benzene).
Claim 5
Dependent Claim
83 words
A radiation curable composition according to claim 1 wherein component (a) is present in an amount ranging from about 5 to about 35 wt wt %, based upon the total weight of component (1), component (b) is present in an amount ranging from about 1 to about 20 wt %, based upon the total weight of component (1) and component (c) is present in an amount ranging from about 50 to about 90 wt %, based upon the total weight of component (1).
Claim 6
Dependent Claim
82 words
A radiation curable composition according to claim 1 wherein component (a) is present in an amount ranging from about 10 to about 30 wt %, based upon the total weight of component (1), component (b) is present in an amount ranging from about 1 to about 10 wt %, based upon the total weight of component (1), and component (c) is present in an amount ranging from about 70 to about 80 wt %, based upon the total weight of component (1).
Claim 7
Dependent Claim
70 words
A radiation curable composition according to claim 1 wherein component (a) is present in an amount of about 23 wt %, based upon the total weight of component (1), component (b) is present in an amount of about 6 wt %, based upon the total weight of component (1), and component (c) is present in an amount of about 71 wt %, based upon the total weight of component (1).
Claim 8
Dependent Claim
94 words
A radiation curable composition according to claim 1 wherein component (a) is the reaction product of hydroxyethylmethacrylate and methylene bis(4-isocyanato benzene) and is present in an amount of 23 wt %, based upon the total weight of component (1), component (b) is hydroxyethylmethacrylate and is present in an amount of 6 wt %, based upon the total weight of component (1) and component (c) is the (meth)acrylated prepolymer of methylene bis(4-isocyanatobenzene) and a polycaprolactone triol and is present in an amount of about 71 wt %, based upon the total weight of component (1).
Claim 9
Dependent Claim
47 words
A radiation curable composition according to claim 1 wherein component (1) further comprises (d) a (meth)acrylated prepolymer of a monomeric or polymeric aromatic isocyanate and at least one polyether polyol with a functionality ≧2 and a molecular weight in the range of about 90 to about 7,000.
Claim 10
Dependent Claim
106 words
A radiation curable composition according to claim 8 wherein component (a) is present in an amount ranging from about 10 to about 50 wt %, based upon the total weight of component (1), component (b) is present in an amount ranging from about 1 to about 20 wt %, based upon the total weight of component (1), component (c) is present in an amount ranging from about 1 to about 10 wt %, based upon the total weight of component (1) and component (d) is present in an amount ranging from about 25 to about 75 wt %, based upon the total weight of component (1).
Claim 11
Dependent Claim
106 words
A radiation curable composition according to claim 8 wherein component (a) is present in an amount ranging from about 20 to about 30 wt %, based upon the total weight of component (1), component (b) is present in an amount ranging from about 5 to about 15 wt %, based upon the total weight of component (1), component (c) is present in an amount ranging from about 1 to about 5 wt %, based upon the total weight of component (1) and component (d) is present in an amount ranging from about 50 to about 75 wt %, based upon the total weight of component (1).
Claim 12
Dependent Claim
90 words
A radiation curable composition according to claim 8 wherein component (a) is present in an amount of about 23 wt %, based upon the total weight of component (1), component (b) is present in an amount of about 6 wt %, based upon the total weight of component (1), component (c) is present in an amount of about 3 wt %, based upon the total weight of component (1) and component (d) is present in an amount of about 68 wt %, based upon the total weight of component (1).
Claim 13
Dependent Claim
129 words
A radiation curable composition according to claim 8 wherein component (a) is the reaction product of hydroxyethylmethacrylate and methylene bis(4-isocyanato benzene) and is present in an amount of about 23 wt %, based upon the total weight of component (1), component (b) is hydroxyethylmethacrylate and is present in an amount of about 6 wt %, based upon the total weight of component (1), component (c) is the (meth)acrylated prepolymer of methylene bis(4-isocyanatobenzene) and a polycaprolactone triol and is present in an amount of about 3 wt %, based upon the total weight of component (1) and component (d) is the (meth)acrylated prepolymer of methylene bis(4-isocyanatobenzene) and a poly(oxypropylene)-poly(oxyethylene) block copolymer and is present in an amount of about 68 wt %, based upon the total weight of component (1).
Claim 14
Dependent Claim
45 words
A radiation curable composition according to claim 1 wherein said aromatic multifunctional epoxy (meth)acrylate is selected from the group consisting of acrylated diglycidyl ether bisphenol A, acrylated epoxy novolacs, amino modified bisphenol A epoxy acrylates, rubber modified acrylated epoxies and fatty acid modified epoxy acrylates.
Claim 15
Dependent Claim
28 words
A radiation curable composition according to claim 1 wherein said aromatic multifunctional epoxy (meth)acrylate is present in an amount of from about 10 to about 60 wt %.
Claim 16
Dependent Claim
28 words
A radiation curable composition according to claim 1 wherein said aromatic multifunctional epoxy (meth)acrylate is present in an amount of from about 10 to about 40 wt %.
Claim 17
Dependent Claim
28 words
A radiation curable composition according to claim 1 wherein said aromatic multifunctional epoxy (meth)acrylate is present in an amount of from about 20 to about 30 wt %.
Claim 18
Dependent Claim
39 words
A radiation curable composition according to claim 1 wherein said free radical polymerization monomer is selected from the group consisting of N-vinyl pyrrolidone, N-vinyl caprolactam, acrylic ester with 3-(2-hydroxyethyl)-2-oxazolidone, 2-propenoic acid-2-[[1-methyl ethoxy carbonyl]amino] ethyl ester N,N-dimethylacrylamide and phenoxyethyl acrylate.
Claim 19
Dependent Claim
28 words
A radiation curable composition according to claim 1 wherein said free radical polymerization monomer is present in an amount of from about 5 to about 40 wt %.
Claim 20
Dependent Claim
28 words
A radiation curable composition according to claim 1 wherein said free radical polymerization monomer is present in an amount of from about 10 to about 30 wt %.
Claim 21
Dependent Claim
28 words
A radiation curable composition according to claim 1 wherein said free radical polymerization monomer is present in an amount of from about 20 to about 30 wt %.
Claim 22
Dependent Claim
129 words
A radiation curable composition with high temperature oil resistance comprising (1) a (meth)acrylated urethane component comprising (a) the reaction product of hydroxyethyl(meth)acrylate and a monomeric or polymeric aromatic isocyanate, and (b) hydroxyethyl(meth)acrylate; (2) an aromatic multifunctional epoxy (meth)acrylate having a molecular weight of less than about 1000; (3) at least one free radical polymerizable monomer selected from the group consisting of N-vinyl pyrrolidone, N-vinyl caprolactam, acrylic ester with 3-(2-hydroxyethyl)-2-oxazolidone, 2-propenoic acid-2-[[1-methyl ethoxy carbonyl]amino] ethyl ester N,N-dimethylacrylamide and phenoxyethyl acrylate; and (4) a free radical photoinitiator, which composition exhibits at 25° C.: (i) a Tg greater than about 45° C., (ii) an elongation of greater than about 3%, (iii) a tensile strength of greater than about 1300 psi and (iv) a shear storage modulus of greater than about 4300 psi.
Claim 23
Dependent Claim
129 words
A radiation curable composition with high temperature oil resistance comprising (1) a (meth)acrylated urethane component comprising (a) the reaction product of hydroxyethyl(meth)acrylate and a monomeric or polymeric aromatic isocyanate, and (b) hydroxyethyl(meth)acrylate; (2) an aromatic multifunctional epoxy (meth)acrylate having a molecular weight of less than about 1000; (3) at least one free radical polymerizable monomer selected from the group consisting of N-vinyl pyrrolidone, N-vinyl caprolactam, acrylic ester with 3-(2-hydroxyethyl)-2-oxazolidone, 2-propenoic acid-2-[[1-methyl ethoxy carbonyl]amino] ethyl ester N,N-dimethylacrylamide and phenoxyethyl acrylate; and (4) a free radical photoinitiator, which composition exhibits at 25° C.: (i) a Tg greater than about 45° C., (ii) an elongation of greater than about 3%, (iii) a tensile strength of greater than about 1300 psi and (iv) a shear storage modulus of greater than about 4300 psi.
Claim 24
Dependent Claim
58 words
A radiation curable composition according to claim 21 wherein component (a) is present in an amount ranging from about 50 to about 99 wt %, based upon the total weight of component (1) and component (b) is present in an amount ranging from about 1 to about 50 wt %, based upon the total weight of component (1).
Claim 25
Dependent Claim
58 words
A radiation curable composition according to claim 21 wherein component (a) is present in an amount ranging from about 80 to about 99 wt %, based upon the total weight of component (1) and component (b) is present in an amount ranging from about 1 to about 20 wt %, based upon the total weight of component (1).
Claim 26
Dependent Claim
49 words
A radiation curable composition according to claim 21 wherein component (a) is present in an amount of about 94 wt %, based upon the total weight of component (1) and component (b) is present in an amount of 6 wt %, based upon the total weight of component (1).
Claim 27
Dependent Claim
33 words
A radiation curable composition according to claim 21 wherein said aromatic isocyanate is selected from the group consisting of methylene bis(4-isocyanato benzene), toluene diisocyanate, 3,3'-diisocyanate, 4,4'-diisocyanate, 3,3'-dimethyl-diphenylmethane-4,4'-diisocyanate, 1,5-diisocyanato-naphthalene, 1,4-diisocyanato-benzene and 1,4- and 1,3-di(isocyanato-dimethyl)-benzene.
Claim 28
Dependent Claim
17 words
A radiation curable composition according to claim 21 wherein said aromatic isocyanate is monomeric methylene bis(4-isocyanato benzene).
Claim 29
Dependent Claim
62 words
A radiation curable composition according to claim 21 wherein component (a) is the reaction product of hydroxyethylmethacrylate and methylene bis(4-isocyanato benzene) and is present in an amount of 94 wt %, based upon the total weight of component (1) and component (b) is hydroxyethylmethacrylate and is present in an amount of 6 wt %, based upon the total weight of component (1).
Claim 30
Dependent Claim
45 words
A radiation curable composition according to claim 21 wherein said aromatic multifunctinal epoxy (meth)acrylate is selected from the group consisting of acrylated diglycidyl ether bisphenol A, acrylated epoxy novolacs, amino modified bisphenol A epoxy acrylates, rubber modified acrylated epoxies and fatty acid modified epoxy acrylates.
Claim 31
Dependent Claim
28 words
A radiation curable composition according to claim 21 wherein said aromatic multifunctional epoxy (meth)acrylate is present in an amount of from about 10 to about 60 wt %.
Claim 32
Dependent Claim
28 words
A radiation curable composition according to claim 21 wherein said aromatic multifunctional epoxy (meth)acrylate is present in an amount of from about 10 to about 40 wt %.
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) | 1996-02-02 | 1996-08-03 | 1997-02-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-02-02 | 2000-08-03 | 2001-02-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-02-02 | 2004-08-03 | 2005-02-02 | $7700.00 | Window Closed / Lapsed |