US5334456A
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Free-radical curable compositions
Assignee: DSM BV
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Filing: 1992-05-26
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Granted: 1994-08-02
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Expires: 2012-05-26
Abstract
Abstract A free-radical radiation curable composition comprising: a) at least one compound containing from one to about six vinyl ether groups; and b) at least one compound containing a saturated backbone and at least one maleate or fumarate end group per molecule, wherein the ratio of vinyl ether groups to maleate or fumarate groups in the composition is in the range of about 5:1 to about 1:5.
Inventors
- 👤 Gerry K. Noren
- 👤 John J. Krajewski
- 👤 Sami A. Shama
- 👤 John M. Zimmerman
- 👤 Danny C. Thompson
- 👤 John T. Vandeberg
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 18:17
CPC Classifications
C; C08; C08F; C08F265/00; C08F265/04; C08F299/00; C08F299/02; C08F299/04; C08F299/0485; C08L; C08L67/00; C08L67/06; C09; C09D; C09D167/00; C09D167/06; C09D167/07; C14; C14C; C14C11/00; C14C11/003; D; D21; D21H; D21H19/00; D21H19/10; D21H19/14; D21H19/16; D21H19/36; D21H19/44; D21H19/46; D21H19/48; G; G03; G03F; G03F7/00; G03F7/004; G03F7/027; G03F7/028; G03F7/029; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31551; Y10T428/31616; Y10T428/3162; Y10T428/31678; Y10T428/31681; Y10T428/31786; Y10T428/3179; Y10T428/31794; Y10T428/31826
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
69 words
A free-radical radiation curable composition comprising: a) at least one compound containing from one to about six vinyl ether groups; and b) at least one compound containing a saturated ester or polyester backbone and at least one maleate and/or fumarate end group per molecule, wherein the ratio of vinyl ether groups to maleate and/or fumarate groups in the composition is in the range of about 2:1 to about 1:2.
Claim 2
Dependent Claim
69 words
A free-radical radiation curable composition comprising: a) at least one compound containing from one to about six vinyl ether groups; and b) at least one compound containing a saturated ester or polyester backbone and at least one maleate and/or fumarate end group per molecule, wherein the ratio of vinyl ether groups to maleate and/or fumarate groups in the composition is in the range of about 2:1 to about 1:2.
Claim 3
Dependent Claim
25 words
The composition of claim 1 that further comprises a compound containing at least one vinyl ether and at least one maleate or fumarate end group.
Claim 4
Dependent Claim
49 words
The composition of claim 1 wherein the compound containing at least one vinyl ether group has a number average molecular weight of about 150 to about 8000 and the compound containing a saturated ester or polyester backbone has a number average molecular weight of about 100 to about 5000.
Claim 5
Dependent Claim
64 words
The composition of claim 1 wherein the compound containing at least one vinyl ether group has the formula: R.sup.3 --(O--CH═CHR.sup.4).sub.m where m is an integer from 1 to 5; R 3 is a residue of an organic alcohol or polyol, essentially free of maleate or fumarate groups, with a molecular weight of from 56 to about 2000; and R 4 is hydrogen or methyl.
Claim 6
Dependent Claim
14 words
The composition of claim 4 wherein the value of m is 2 to 4.
Claim 7
Dependent Claim
80 words
The composition of claim 1 wherein component b has the formula: ##STR13## where n is an integer from 1 to 5; R 1 is the residue of an organic alcohol or polyol, essentially free of maleate, fumarate, or urethane groups, with a molecular weight of from 15 to about 2000; and R 2 is hydrogen, alkyl, cycloalkyl, or aryl or alkaryl, with 1 to 15 carbon atoms and at least one optional O or N heteroatom, or a metal iron.
Claim 8
Dependent Claim
17 words
The composition of claim 6 wherein R 1 is the residue of a hydroxy terminated saturated polyester.
Claim 9
Dependent Claim
14 words
The composition of claim 6 wherein the value of n is 2 to 4.
Claim 10
Dependent Claim
40 words
The composition of claim 6 wherein R 2 is CH 3 (CH 2 ) x --(--O--CH 2 CHR 8 ) y -- where x is 0 to 5; Y is 0 to 3; and R 8 is hydrogen or methyl.
Claim 11
Dependent Claim
51 words
The composition of claim 6 wherein n is 2 R 1 is --(CH 2 ) p -CHR 9 --]O--(CH 2 ) p --CHR 9 --] q -- where p is an integer from 1 to 5; q is an integer from 0 to 20; and R 9 is hydrogen or methyl.
Claim 12
Dependent Claim
20 words
The composition of claim 1 wherein the ratio of vinyl ether groups to maleate and/or fumarate groups is about 1:1.
Claim 13
Dependent Claim
28 words
The composition of claim 1 that further comprises 0.1 to 10 weight percent based on the total weight of the composition of at least one free radical photoinitiator.
Claim 14
Dependent Claim
80 words
The composition of claim 12 wherein the photoinitiator is ##STR14## where R m is an optional alkyl or aryl hydrocarbon substitutent containing from 1 to 10 carbon atoms, and x is selected from the group consisting of hydroxy, C 1 to C 4 alkyoxy, C 1 to C 8 alkyl, cycloalkyl, halogen, and phenyl, or 2 Xs together are cycloalkyl, and at least one X is selected from the group consisting of hydroxy and C 1 to C 4 alkoxy.
Claim 15
Dependent Claim
35 words
The composition of claim 12 wherein the photoinitiator is ##STR15## where R q is an optional hydrocarbon substitutent containing from 1 to 10 carbon atoms; and x is independently an integer from 1 to 3.
Claim 16
Dependent Claim
70 words
A compound of the formula: ##STR16## where R 5 is hydrogen, alkyl, cycloalkyl, an aryl or alkaryl group with 1 to 10 carbon atoms and at least one optional O or N heteroatom, or a metal ion; R 6 is alkyl, cycloalkyl, or an aryl or alkaryl group with 1 to 10 carbon atoms and at least one optional O or N heteroatom; and R 7 is hydrogen or methyl.
Claim 17
Dependent Claim
70 words
A compound of the formula: ##STR16## where R 5 is hydrogen, alkyl, cycloalkyl, an aryl or alkaryl group with 1 to 10 carbon atoms and at least one optional O or N heteroatom, or a metal ion; R 6 is alkyl, cycloalkyl, or an aryl or alkaryl group with 1 to 10 carbon atoms and at least one optional O or N heteroatom; and R 7 is hydrogen or methyl.
Claim 18
Dependent Claim
93 words
The composition of claim 1 that further comprises up to about 80 weight percent based on the total weight of the composition of a dual functional monomer of the formula: ##STR17## where R 5 is hydrogen, alkyl, cycloalkyl, an aryl or alkaryl group, with 1 to 10 carbon atoms and an optional O or N heteroatom, or a metal ion; R 6 is alkyl, cycloalkyl, or an aryl or alkaryl group with 1 to 10 carbon atoms and at least one optional O or N heteroatom; and R 7 is hydrogen or methyl.
Claim 19
Dependent Claim
42 words
The composition of claim 1 that further comprises up to about 40 percent based on the total weight of the composition by weight of at least one additive selected from the group consisting of pigments, fillers, wetting agents, stabilizers and combinations thereof.
Claim 20
Dependent Claim
17 words
The composition of claim 1 wherein the compound containing the vinyl ether group is triethyleneglycol divinyl ether.
Claim 21
Dependent Claim
18 words
The composition of claim 1 wherein the compound containing the vinyl ether group is 1,4-cyclohexane dimethanol divinyl ether.
Claim 22
Dependent Claim
20 words
The composition of claim 1 wherein the compound containing the vinyl ether group is a vinyl ether terminated urethane oligomer.
Claim 23
Dependent Claim
46 words
The composition of claim 1 that further comprises up to 50 weight percent based on the total weight of the composition of acrylate or methacrylate terminated monomers or oligomers with equivalent weights ranging from about 250 to 5000 and average functionalities from about 1 to 4.
Claim 24
Dependent Claim
9 words
A substrate coated with a composition of claim 1.
Claim 25
Dependent Claim
10 words
A substrate coated with a cured composition of claim 1.
Claim 26
Dependent Claim
30 words
The coated substrate in accordance with claim 22 or 20, wherein the substrate is selected from the group of glass, paper, wood, rubber, metal, concrete leather, fabric, fiber and plastic.
Claim 27
Dependent Claim
164 words
A free-radical radiation curable composition comprising: (a) at least one vinyl ether compound of the formula: R.sup.3 --(O--CH═CHR.sup.4).sub.m where m is an integer from 1 to 5; R 3 is the residue of an organic alcohol or polyol, essentially free of maleate or fumarate groups, with a molecular weight of from 50 to about 2,000; and R 4 is hydrogen or methyl; and (b) at least one compound of the formula: ##STR18## where n is an integer from 1 to 5; R 1 is the residue of an organic alcohol or polyol, essentially free of maleate, fumarate or urethane groups, with a molecular weight of from 15 to about 2,000; and R 2 is hydrogen, alkyl, cycloalkyl, aryl or alkenyl having 1 to 15 carbon atoms and at least one optional O or N heteroatom, or a metal ion; wherein the ratio of vinyl ether groups to maleate and/or fumarate groups in the composition is in the range of about 2:1 to about 1:2.
Claim 28
Dependent Claim
164 words
A free-radical radiation curable composition comprising: (a) at least one vinyl ether compound of the formula: R.sup.3 --(O--CH═CHR.sup.4).sub.m where m is an integer from 1 to 5; R 3 is the residue of an organic alcohol or polyol, essentially free of maleate or fumarate groups, with a molecular weight of from 50 to about 2,000; and R 4 is hydrogen or methyl; and (b) at least one compound of the formula: ##STR18## where n is an integer from 1 to 5; R 1 is the residue of an organic alcohol or polyol, essentially free of maleate, fumarate or urethane groups, with a molecular weight of from 15 to about 2,000; and R 2 is hydrogen, alkyl, cycloalkyl, aryl or alkenyl having 1 to 15 carbon atoms and at least one optional O or N heteroatom, or a metal ion; wherein the ratio of vinyl ether groups to maleate and/or fumarate groups in the composition is in the range of about 2:1 to about 1:2.
Claim 29
Dependent Claim
15 words
A composition as in claim 25 where n is an integer from 2 to 4.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1997-08-01 | 1998-01-31 | 1998-08-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2001-08-01 | 2002-01-31 | 2002-08-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2005-08-01 | 2006-01-31 | 2006-08-02 | $7700.00 | Window Closed / Lapsed |