Energy curable compositions: two component curing agents
First Claim
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1. A method comprising the steps of:
- (a) providing a mixture comprising a polymeric precursor composition selected from the group consisting of(1) at least one di- and polysiocyanates, and at least one compound bearing at least two isocyanate-reactive hydrogen aotms, the isocyanate and reactive hydrogen-containing compound constituting polyurethane precursors, and(2) at least one ethylenically-unsaturated compound, at least one isocyanate selected from di- and polyisocyanates, and at least one compound bearing at least two isocyanate-reactive hydrogen atoms, the isocyanate and reactive hydrogen-containing compound constituting polyurethane precursors, anda catalytically effective amount of a two-component curing agent for (1) and (2) comprising(1) an organometallic salt, and(2) an onium salt;
(b) allowing said mixture to polymerize or adding energy to said mixture to effect polymerization.
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Abstract
A polymerizable composition comprises a polymeric precursor selected from the group consisting of (1) at least one ethylenically-unsaturated monomer, optionally in combination with an epoxy monomer or polyurethane precursors, or (2) at least one epoxy monomer, or (3) polyurethane precursors, and a curing agent comprising an organometallic salt and an onium salt.
330 Citations
42 Claims
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1. A method comprising the steps of:
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(a) providing a mixture comprising a polymeric precursor composition selected from the group consisting of (1) at least one di- and polysiocyanates, and at least one compound bearing at least two isocyanate-reactive hydrogen aotms, the isocyanate and reactive hydrogen-containing compound constituting polyurethane precursors, and (2) at least one ethylenically-unsaturated compound, at least one isocyanate selected from di- and polyisocyanates, and at least one compound bearing at least two isocyanate-reactive hydrogen atoms, the isocyanate and reactive hydrogen-containing compound constituting polyurethane precursors, and a catalytically effective amount of a two-component curing agent for (1) and (2) comprising (1) an organometallic salt, and (2) an onium salt; (b) allowing said mixture to polymerize or adding energy to said mixture to effect polymerization. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 33, 34, 39)
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12. The method according to claim 1 wherein said two-component curing agent is present in the range of 0.01 to 20 weight percent of the total composition.
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13. The method according to claim 12 wherein said two-component curing agent is present in the range of 0.1 to 10 weight percent of said total composition.
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14. The method according to claim 1 wherein the ratio of organometallic compound to onium salt of said curing agent is in the range of 10:
- 1 to 1;
10 by weight.
- 1 to 1;
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15. The method according to claim 1 wherein the ratio of organometallic salt to onium salt is in the range of 5:
- 1 to 1;
5 by weight.
- 1 to 1;
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16. The method according to claim 1, wherein said ethylenically-unsaturated monomer is selected from the group consisting of acrylates, acrylamides, vinyl compounds, and bireactive monomers.
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17. The method according to claim 16 wherein said ethylenically-unsaturated monomer is an acrylate or methacrylate.
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18. The method according to claim 1 wherein said polymeric precursor is at least one ethylenically-unsaturated compound, at least one isocyanate selected from di- and polyisocyanates, and at least one compound bearing at least two isocyanate-reactive hydrogen atoms, the isocyanate and reactive hydrogen-containing compound constituting polyurethane precursors.
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20. The method according to claim 1 wherein said organometallic compound is selected from the group consisting of (eta6 -mesitylene)(eta5 -cyclopentadienyl)iron(1+) hexafluoroantimonate, (eta6 -mesitylene)(eta5 -cyclopentadienyl)iron(1+) hexafluorophosphate, (eta6 -naphthalene)(eta5 -cyclopentadienyl)iron(1+), hexafluoroantimonate, (eta6 -naphthalene)(eta5 -cyclopentadienyl)iron(1+)hexafluoro phosphate, (eta5 -cyclopentadienyl)dicarbonyltriphenylphosphineiron(1+) hexafluorophosphate, and (eta5 -cyclopentadienyl)dicarbonyl-triphenylphosphineiron (1+) hexafluoroantimonate.
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21. The method according to claim 1 wherein said onium salt is at least one of Ph2 I+ PF6-, Ph3 I+ SbF6-, Ph2 I+ AsF6-, Ph2 I+ SbF5 (OH)-, Ph3 S+ PF6-, Ph2 S+ SbF6-, Ph3 S+ AsF6-, PhSC6 H4 SPh2+SbF6-, and Ph3 S+ SbF5 (OH)-, wherein Ph is phenyl.
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22. The method according to claim 1 wherein said polymerizable mixture further comprises up to 90 weight percent of a solvent based on the total mixture.
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33. A cured composition prepared according to the method of claim 1 wherein said di- and polysiocyanates have reactive functionality consisting essentially of socyanate groups, and said at least one other polyurethane precursor has reactive functionality consisting essentially of at least two isocyanate-reactive hydrogen atoms.
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34. A shaped article according to claim 33.
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39. The method according to claim 1 wherein said at least one ethylenically-unsaturated monomer as disclosed in (a) (2) comprises at least one ethylenically-unsaturated monomer and at least one bireactive monomer different from said ethylenically-unsaturated monomer.
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19. The method according to claim l wherein said polyurethane precursors comprise a mixture of polyisocyanates and compounds bearing at least two isocyanate-reactive hydrogen atoms where the ratio of isocyanate groups to isocyanate-reactive hydrogen atoms is in the range 1:
- 2 to 2;
1.
- 2 to 2;
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23. A polymerizable composition comprising a polymeric precursor selected from one of the groups consisting of
(1) at least one isocyanate selected from di- and polyisocyanates, and at least one compound bearing at least two isocyanate-reactive hydrogen atoms, the isocyanate and reactive hydrogen-containing compound constituting polyurethane precursors, and (2) at least one ethylenically-unsaturated monomer, at least one isocyanate selected from di- and polyisocyanates, and at least one compound bearing at least two isocyanate-reactive hydrogen atoms, the isocyanate and reactive hydrogen-containing compound constituting polyurethane precursors, and a two-component curing agent for (1) and (2) comprising an organometallic salt and an onium salt. - View Dependent Claims (24, 25, 26, 27, 28, 29, 30, 31, 32, 35, 36, 37, 38, 40, 41, 42)
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35. A layered structure comprising a substrate having coated on at least one surface thereof the polymerizable composition according to claim 23.
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36. The cured structure according to claim 35 wherein said di- and polyisocyanates have reactive functionality consisting essentially of isocyanate groups, and said at least one other polyurethane precursor has reactive functionality consisting essentially of at least two isocyanate-reactive hydrogen atoms.
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37. The layered structure according to claim 35 which is an imageable structure.
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38. The composition according to claim 23 further comprising an effective amount of a photosensitizer.
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40. The composition according to claim 23 wherein said ethylenically-unsaturated monomer is selected from the group consisting of acrylates, acrylamides, vinyl compounds, and bireactive monomers.
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41. The composition according to claim 23 wherein said at least one ethylenically-unsaturated monomer as disclosed in (2) comprises at least one ethylenically-unsaturated monomer and at least one bireactive monomer different from said ethylenically-unsaturated monomer.
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42. The composition according to claim 23 wherein said polymeric precursor comprises at least one ethylenically-unsaturated compound, at least one isocyanate selected from di- and polyisocyanates, and at least one compound bearing at least two isocyanate-reactive hydrogen atoms, the isocyanate and reactive hydrogen-containing compound constituting polyurethane precursors.
Specification