Claims
- 1. A radiation curable resin composition comprising an isocyanuric ring-containing uretahen modified radical polymerizable compound selected from the group consisting of
- (A) a reaction product of at least one polyisocyanate compound with a di(meth)acrylate of isocyanuric acid represented by the following general formula ##STR7## wherein R.sub.1 represents a hydrogen atom or a methyl group, R.sub.2 represents an alkyl group having 1 to 5 carbon atoms, and m is an integer of 1 to 20; and
- (B) a reaction product of at least one polyisocyanate compound, a di(meth)acrylate of isocyanuric acid represented by the following general formula ##STR8## wherein X's are identical or different and each represents an alkylene group or a group resulting from substitution of a hydroxyl group for one hydrogen atom in the alkylene group, R.sub.3 and R.sub.4 each represent an acryloyl group and/or a methacryloyl group, and n is an integer of 1 to 20,
- and 2-hydroxxyethylacrylate, 2-hydroxypropyl acrylate or a mixture thereof as a hydroxyl group-containing radical-polymerizable compound.
- 2. The composition of claim 1 wherein the isocyanuric ring-containing urethane-modified radical-polymerizable compound is said reaction product of at least one polyisocyanate compound with a di(meth)acrylate of isocyanuric acid represented by the following general formula ##STR9## wherein R.sub.1 represents a hydrogen atom or a methyl group, R.sub.2 represents an alkyl group having 1 to 5 carbon atoms, and m is an integer of 1 to 20.
- 3. The composition of claim 1 wherein the isocyanuric ring-containing urethane-modified radical-polymerizable compound is said reaction product of at least one polyisocyanate compound, a di(meth)acrylate of isocyanuric acid represented by the following general formula ##STR10## wherein X's are identical or different and each represents an alkylene group or a group resulting from substitution of a hydroxyl group for one hydrogen atom in the alkylene group, R.sub.3 and R.sub.4 each represent an acrylol group and/or a methacryloyl group, and n is an integer of 1 to 20,
- and 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate or a mixture thereof, as a hydroxyl group-containing radical-polymerizable compound.
- 4. The composition of claim 2 wherein the isocyanuric ring-containing urethane-modified radical-polymerizable compound is a reaction product of at least one polyisocyanate compound, and a (meth)acrylate of isocyanuric acid composed of 40 to 95% by weight of a di(meth)acrylate of isocyanuric acid represented by the following general formula ##STR11## wherein R.sub.1 represents a hydrogen atom or a methyl group, R.sub.2 represents an alkyl group having 1 to 5 carbon atoms, and m is an integer of 1 to 20,
- 2. 5 to 30% by weight of a mono(meth)acrylate of isocyanuric acid represented by the general formula ##STR12## wherein R.sub.1 represents a hydrogen atom or a methyl group, R.sub.2 represents an alkyl group having 1 to 5 carbon atoms, and m is an integer of 1 to 20,
- and 2.5 to 30% by weight of a tri(meth)acrylate of isocyanuric acid represented by the general formula ##STR13## wherein R.sub.1 represents a hydrogen atom or a methyl group, R.sub.2 represents an alkyl group having 1 to 5 carbon atoms, and m is an integer of 1 to 20.
- 5. The composition of claim 3 wherein the isocyanuric ring-containing urethane-modified radical-polymerizable compound is a reaction of at least one polyisocyanate compound, and a (meth)acrylate of isocyanuric acid composed of 40 to 90% by weight of a di(meth)-acrylate of isocyanuric acid represented by the following general formula ##STR14## wherein X's are identical or different and each represents an alkylene group having 1 to 5 carbon atoms or a group resulting from substitution of a hydroxyl group for one hydrogen atom in the alkylene group, R.sub.3 and R.sub.4 each represent an acryloyl group and/or a methacryloyl group, and n is an integer of 1 to 20,
- 2. 5 to 30% by weight of a mono(meth)acrylate of isocyanuric acid represented by the general formula ##STR15## wherein X's, R.sub.3 and n are as defined above, and 2.5 to 30% by weight of a tri(meth)acrylate of isocyanuric acid represented by the general formula ##STR16## wherein X's, R.sub.3, R.sub.4 and n are as defined above, and R.sub.5 represents an acrylol or methacryloyl group, and 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate or a mixture thereof, as a hydroxyl group-containing radical-polymerizable compound.
- 6. The composition of claim 2 wherein the polyisocyanate compound is selected from the group consisting of 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 1,4-xylylene diisocyanate, diphenylmethane 4,4-diisocyanate, 3-methyldiphenylmethane diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, dicyclohexylmethane 4,4'-diisocyanate, dicyclohexylmethane 2,4'-diisocyanate, lysine diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated diphenylmethane 4,4'-diisocyanate, polyisocyanates obtained by polymerizing divalent or trivalent polyisocyanate compounds, and isocyanate-terminated urethane prepolymers obtained by reacting at least one of the aforementioned polyisocyanate compounds with a polyol compound having at least two hydroxy groups per molecule, and a number average molecular weight of 62 to 20,000, the equivalent ratio of the hydroxyl groups of the polyol compound to the isocyanate groups of the polyisocyanate compound being 1:1.2-3.
- 7. The composition of claim 3 wherein the polyisocyanate compound is selected from the group consisting of 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 1,4-xylylene diisocyanate, diphenylmethane, 4,4-diisocyanate, 3-methyldiphenylmethane diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, dicyclohexylmethane 4,4'-diisocyanate, dicyclohexylmethane 2,4'-diisocyanate, lysine diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated diphenylmethane 4,4'-diisocyanate, polyisocyanates obtained by polymerizing divalent or trivalent polyisocyanate compounds, and isocyanate-terminated urethane prepolymers obtained by reacting at least one of the aforementioned polyisocyanate compounds with a polyol compound having at least two hydroxy groups per molecule, and a number average molecular weight of 62 to 20,000, the equivalent ratio of the hydroxyl groups of the polyol compound to the isocyanate groups of the polyisocyanate compound being 1:1.2-3.
- 8. The composition of claim 4 wherein the polyisocyanate compound is selected from the group consisting of 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 1,4-xyylene diisocyanate, diphenylmethane 4,4-diisocyanate, 3-methyldiphenylmethane diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, dicyclohexylmethane 4,4'-diisocyanate, dicyclohexylmethane 2,4'-diisocyanate, lysine diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated diphenylmethane 4,4'-diisocyanate, polyisocyanates obtained by polymerizing divalent or trivalent polyisocyanate compounds, and isocyanate-terminated urethane prepolymers obtained by reacting at least one of the aforementioned polyisocyanate compounds with a polyol compound having at least two hydroxy groups per molecule, and a number average molecular weight of 62 to 20,000, the equivalent ratio of the hydroxyl groups of the polyol compound to the isocyanate groups of the polyisocyanate compound being 1:1.2-3.
- 9. The composition of claim 5 wherein the polyisocyanate compound is selected from the group consisting of 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 1,4-xylene diisocyanate, diphenylmethane 4,4-diisocyanate, 3-methyldiphenylmethane diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, dicyclohexylmethane 4,4'-diisocyanate, dicyclohexylmethane 2,4'-diisocyanate, lysine diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated diphenylmethane 4,4'-diisocyanate, polyisocyanates obtained by polymerizing divalent or trivalent polyisocyanate compounds, and isocyanate-terminated urethane prepolymers obtained by reacting at leasst one of the aforementioned polyisocyanate compounds with a polyol compound having at least two hydroxy groups per molecule, and a number average molecular weight of 62 to 20,000, the equivalent ratio of the hydroxyl groups of the polyol compound to the isocyanate groups of the polyisocyanate compound being 1:1.2-3.
- 10. The composition of claim 2 useful for forming protective coatings and further comprising at least one additional component other than the isocyanuric ring-containing urethane-modified radical-polymerizable compound and selected from one or more of the following: film-forming prepolymers having at least two radical-polymerizable double bonds per molecule, reactive diluents, photopolymerization initiators, photopolymerization promoters, thermally decomposible catalyst components, pigments, fillers, adhesion promoters, flow improvers, non-radical polymerizable modifying resins, polymerization inhibitors, ultraviolet absorbers, antistatic agents, dyeability imparting agents, solvents and mixtures thereof.
- 11. The composition of claim 3 useful for forming protective coatings and further comprising at least one additional component other than the isocyanuric ring-containing urethane-modified radical-polymerizable compound and selected from one or more of the following: film-forming prepolymers having at least two radical-polymerizable double bonds per molecule, reactive diluents, photopolymerization initiators, photopolymerization promoters, thermally decomposible catalyst components, pigments, fillers, adhesion promoters, flow improvers, non-radical polymerizable modifying resins, polymerization inhibitors, ultraviolet absorbers, antistatic agents, dyeability imparting agents, solvents and mixtures thereof.
- 12. The composition of claim 4 useful for forming protective coatings and further comprising at least one additional component other than the isocyanuric ring-containing urethane-modified radical-polymerizable compound and selected from one or more of the following: film-forming prepolymers having at least two radical-polymerizable double bonds per molecule, reactive diluents, photopolymerization initiators, photopolymerization promoters, thermally decomposible catalyst components, pigments, fillers, adhesion promoters, flow improvers, non-radical polymerizable modifying resins, polymerization inhibitors, ultraviolet absorbers, antistatic agents, dyeability imparting agents, solvents and mixtures thereof.
- 13. The composition of claim 5 useful for forming protective coatings and further comprising at least one additional component other than the isocyanuric ring-containing urethane-modified radical-polymerizable compound and selected from one or more of the following: film-forming prepolymers having at least two radical-polymerizable double bonds per molecule, reactive diluents, photopolymerization initiators, photopolymerization promoters, thermally decomposible catalyst components, pigments, fillers, adhesion promoters, flow improvers, non-radical polymerizable modifying resins, polymerization inhibitors, ultraviolet absorbers, antistatic agents, dyeability imparting agents, solvents and mixtures thereof.
Parent Case Info
This application is a continuation-in-part application of U.S. Ser. No. 517,269 filed July 26, 1983, now abandoned.
US Referenced Citations (7)
Foreign Referenced Citations (2)
Number |
Date |
Country |
129018 |
Aug 1983 |
JPX |
26337 |
Mar 1984 |
JPX |
Non-Patent Literature Citations (1)
Entry |
Chemical Abstracts 81:154746g (1974), Toray. |
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
517269 |
Jul 1983 |
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