Activation energy-curable resin composition

• US 4,690,987 A
• Filed: 05/23/1985
• Issued: 09/01/1987
• Est. Priority Date: 05/28/1984
• Status: Expired due to Fees

• Current Assignee: Dainippon Ink and Chemicals Incorporated
• Original Assignee: Dainippon Ink and Chemicals Incorporated
• Inventors: Maruyama, Osamu, Ishikawa, Hidenobu, Sakakibara, Shigeru, Arimoto, Shunji
• Primary Examiner(s): Bleutge, John C.
• Assistant Examiner(s): SELLERS, ROBERT E
• Application Number:
  US06/737,254
• Time in Patent Office: 831 Days
• Field of Search: 525/528, 525/530, 525/507, 525/502, 525/920, 525/504, 522/92
• US Class Current: 525/502
• CPC Class Codes: C08G 18/6705 Unsaturated polymers not provided for in the groups C08G18/671, C08G18/6795, C08G18/68 or C08G18/69
• CPC Class Codes: C08G 18/8175 with esters of acrylic or alkylacrylic acid having only one group containing active hydrogen
• CPC Class Codes: C08L 63/10 Epoxy resins modified by unsaturated compounds
• CPC Class Codes: C08L 75/04 Polyurethanes
• CPC Class Codes: Y10S 525/92 Polyurethane having terminal ethylenic unsaturation

Abstract

An activation energy-curable resin composition comprising as an essential ingredient a resin obtained by reacting (a) the reaction product of a novolac epoxy compound and an unsaturated monocarboxylic acid with (b) the reaction product of a diisocyanate and a poly(meth)acrylate having one hydroxyl group for each molecule.

Claims

1. An activation energy-curable resin composition comprising as an essential ingredient a resin obtained by reacting (a) the reaction product of a novolac epoxy compound and an unsaturated monocarboxylic acid with (b) the reaction product of a diisocyanate and a polyacrylate or polymechacrylate ester of a polyol wherein the final structure has one hydroxyl group for each molecule.

2. The composition of claim 1 wherein the reaction product (a) is the reaction product of acrylic or methacrylic acid with a phenol novolac epoxy resin obtained by the addition reaction of a polycondensate of phenol and formaldehyde with epichlorohydrin or beta-methylepichlorohydrin.

3. The composition of claim 1 wherein the reaction product (a) is the reaction product of acrylic or methacrylic acid with an alkylphenol novolac epoxy resin obtained by the addition reaction of a polycondensate of an (C₁ -C₉ alkyl)phenol and formaldehyde with epichlorohydrin or beta-methylepichlorohydrin.

4. The composition of claim 1 wherein the reaction product (a) is the reaction product of a cresol novolac epoxy resin with acrylic or methacrylic acid.

5. The composition of any one of claims 1 to 4 wherein the reaction product (a) is obtained by using a novolac epoxy compound having 3 to 8 phenol nuclei.

6. The composition of any one of claims 1 to 4 wherein the reaction product (a) is obtained by reacting the novolac epoxy compound and the unsaturated monocarboxylic acid in such proportions that the equivalent ratio of the epoxy groups of the former to the carboxyl group of the latter is 1.0-1.7:

1.0.

7. The composition of claim 1 wherein the reaction product (b) is a reaction product of at least one polyacrylate or polymethacrylate ester of a polyol wherein the final structure has 1 hydroxyl group per molecule which is selected from the group consisting of pentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, trimethylolpropane di(meth)acrylate, glycerin di(meth)acrylate and tris(hydroxyethyl)isocyanurate di(meth)acrylate with at least one diisocyanate selected from the group consisting of 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, xylylene-1,4-diisocyanate, hydrogenated xylylene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, diphenylmethane diisocyanate, toluidine diisocyanate and lysine diisocyanate.

8. The composition of claim 1 or 7 wherein the reaction product (b) is obtained by reacting the polyacrylate or polymethacrylate ester of a polyol wherein the final structure has 1 hydroxyl group per molecule and the diisocyanate in such proportions that the equivalent ratio of the hydroxyl groups of the former to the isocyanate groups of the latter is in the range of 1.0:

2.0 to 1.3;

2.0.

9. The composition of claim 6 wherein the novolak epoxy compound has 3 to 8 phenol nuclei.

10. The composition of claim 1 wherein the resin is obtained by reacting the reactants (a) and (b) in such proportions that the equivalent ratio of the isocyanate groups of the reaction product (b) to the hydroxyl groups of the reaction product (a) is within the range of 1.0:

1.0 to 0.1;

1.0.

11. The composition of claim 10 wherein the ratio is 0.8:

1.0 to 0.2;

1.0.

12. The composition of claim 1 which is curable by exposure to ultraviolet light and further comprising a photoreaction accelerator for initiating the polymerization of the resin component by ultraviolet light.

13. The composition of claim 12 wherein the photoreaction accelerator is selected from the group consisting of benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin formate, 1-hydroxy-1-benzoylcyclohexane, dibutoxyacetophenone, alpha-hydroxy-iso-butyrophenone, p-isopropyl-alpha-methoxyisobutyrophenone, benzyl diphenyl disulfide and azobisisobutyronitrile.