Monomer mixture and curable composition containing same

Patent metadata

Field	Value
Publication number	US-11028225-B2
Application number	US-201816615481-A
Country	US
Kind code	B2
Filing date	Jul 19, 2018
Priority date	Jul 28, 2017
Publication date	Jun 8, 2021
Grant date	Jun 8, 2021

Abstract

Provided is a monomer mixture that is rapidly cured to form a cured product having high hardness, excellent alkali resistance, and excellent adhesion to a substrate. The monomer mixture of the present invention is a monomer mixture containing at least: a compound represented by Formulas (a-1) and/or (a-2); a compound (2B) including two cationically polymerizable groups per molecule, at least one of the cationically polymerizable groups being an epoxy group; a compound (3B) including three or more cationically polymerizable groups per molecule, at least one of the cationically polymerizable groups being an epoxy group; and a compound represented by Formula (c-1).

First claim

The invention claimed is:

1. A monomer mixture containing at least:
a compound represented by Formulas (a-1) and/or (a-2):

a compound (2B′), represented by Formula (2b-1):

where X represents a single bond or a linking group;
a compound (3B′) represented by Formula (3b-1):

where each R′ represents an aliphatic hydrocarbon group, and s represents an integer of 3 to 6, and
a compound represented by Formula (c-1):

wherein a total content of the compound represented by Formula (a-1) and the compound represented by Formula (a-2) is from 1 to 20 wt. % of a total amount of the monomer mixture;
a content of the compound represented by Formula (c-1) is from 5 to 95 wt. % of the total amount of the monomer mixture, and
the monomer mixture meets one of conditions [1] and [2] as follows:
[1] a weight ratio of contents of the compound (2B′)/the compound (3B′) is from 0.1 to 0.8; and
[2] a weight ratio of contents of the compound (2B′)/the compound (3B′) is from greater than 0.8 to 1.8, and a content of a compound or compounds containing two or more oxetanyl groups per molecule, including the compound represented by Formula (c-1), is from 45 to 95 wt. % of the total amount of the monomer mixture.

2. The monomer mixture according to claim 1 , wherein a total content of the compound (2B′) and the compound (3B′) is from 10 to 50 wt. % of the total amount of the monomer mixture, and
a content of the compound represented by Formula (c-1) is from 5 to 80 wt. % of the total amount of the monomer mixture.

3. The monomer mixture according to claim 1 , wherein the compound (2B′) is a compound represented by Formula (2b-1):

where X represents a linking group.

4. The monomer mixture according to claim 1 , wherein the “s” in Formula (3b-1) is an integer of 3.

5. The monomer mixture according to claim 1 , wherein a content of a compound including only one cationically polymerizable group selected from a vinyl ether group, an epoxy group, and an oxetanyl group per molecule is 30 wt. % or less of the total amount of the monomer mixture.

6. A curable composition comprising the monomer mixture described in claim 1 and a curing catalyst.

7. The curable composition according to claim 6 , comprising a sensitizer, or a sensitizer and a sensitization auxiliary agent.

8. The curable composition according to claim 6 , containing a coloring material.

9. The curable composition according to claim 6 , containing a dispersant.

10. The curable composition according to claim 6 , which is an ultraviolet-curable inkjet ink.

11. A method of producing a molded article comprising: ejecting the curable composition described in claim 10 using an inkjet method, then curing the ejected curable composition, and forming a molded article from a cured product of the curable composition.

12. A cured product of the curable composition described in claim 6 .

13. A molded article comprising the cured product described in claim 12 .

14. A structure comprising the cured product described in claim 12 on a substrate surface.

15. The monomer mixture according to claim 1 , wherein the compound (2B′) is at least one compound selected from 3,4-epoxycyclohexylmethyl(3,4-epoxy)cyclohexane carboxylate, (3,4,3′,4′-diepoxy)bicyclohexyl, bis(3,4-epoxycyclohexylmethyl)ether, 1,2-epoxy-1,2-bis(3,4-epoxycyclohexan-1-yl)ethane, 2,2-bis(3,4-epoxycyclohexan-1-yl)propane, and 1,2-bis(3,4-epoxycyclohexan-1-yl)ethane.

16. The monomer mixture according to claim 1 , wherein the compound (3B′) is at least one compound selected from trimethylolethane triglycidyl ether, trimethylolpropane triglycidyl ether, pentaerythritol triglycidyl ether, pentaerythritol tetraglycidyl ether, glycerin triglycidyl ether, and dipentaerythritol hexaglycidyl ether.

17. The monomer mixture according to claim 1 , wherein the compound (2B′) is a compound represented by Formula (2b-1):

where X represents a single bond.

18. The monomer mixture according to claim 1 , wherein the “s” in Formula (3b-1) is an integer of 4-6.

Assignees

• Daicel Corp

Inventors

• Mizuta Tomoya
• Inoue Keizo

Classifications

• C08G65/18

  Oxetanes · CPC title

• C09D11/101

  Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing · CPC title

• C08L63/00

  Compositions of epoxy resins; Compositions of derivatives of epoxy resins · CPC title

• C08G65/26 Primary

  from cyclic ethers and other compounds · CPC title

• C09D11/30 Primary

  Inkjet printing inks · CPC title