Monomer mixture and curable composition containing same

Patent metadata

Field	Value
Publication number	US-11339245-B2
Application number	US-201816611296-A
Country	US
Kind code	B2
Filing date	Jul 19, 2018
Priority date	Jul 28, 2017
Publication date	May 24, 2022
Grant date	May 24, 2022

Abstract

The present invention is to provide a monomer mixture that is cured rapidly even in the presence of oxygen and that forms a cured product having high hardness and excellent adhesion to metals and/or glass. The monomer mixture according to an embodiment of the present invention contains two or more types of cationically polymerizable monomers. As the cationically polymerizable monomers, the monomer mixture contains at least 10 wt. %, based on a total amount of the monomer mixture, of a compound having at least one cationically polymerizable group selected from the group consisting of a vinyl ether group, an epoxy group, and an oxetanyl group, and at least one hydroxy group in a molecule, and at least 5 wt. %, based on the total amount of the monomer mixture, of a compound represented by Formula (b). In the formula, R represents an s-valent straight-chain or branched saturated aliphatic hydrocarbon group or an s-valent group having two or more straight-chain or branched saturated aliphatic hydrocarbon groups bonded to each other through an ether bond, and s represents an integer of 2 or greater.

First claim

The invention claimed is:

1. A monomer mixture comprising two or more types of cationically polymerizable monomers,
the monomer mixture comprising:
not less than 10 wt. %, based on a total amount of the monomer mixture, of a compound (I);
not less than 5 wt. %, based on the total amount of the monomer mixture, of a compound (b); and
15 to 50 wt. %, based on the total amount of the monomer mixture, of a compound (b′), and
the monomer mixture having a weight ratio of the compound (I) to the compound (b) of from 1.1 to 5.5,
where:
the compound (I) has at least one cationically polymerizable group selected from the group consisting of a vinyl ether group, an epoxy group, and an oxetanyl group, and at least one hydroxy group in a molecule,
the compound (b) is represented by Formula (b):

where R represents an s-valent straight-chain or branched saturated aliphatic hydrocarbon group or an s-valent group having two or more straight-chain or branched saturated aliphatic hydrocarbon groups bonded to each other through an ether bond, and s represents an integer of 2 or greater, and
the compound (b′) is represented by Formula (b′):

where X represents a single bond or a linking group;
the monomer mixture further comprising:
at least one of a compound represented by Formula (a-1) and a compound represented by Formula (a-2):

2. The monomer mixture according to claim 1 , wherein a content of a compound having one cationically polymerizable group selected from the group consisting of a vinyl ether group, an epoxy group, and an oxetanyl group and having no hydroxy group in a molecule is less than 30 wt. % based on the total amount of the monomer mixture.

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

4. The curable composition according to claim 3 , comprising a sensitizer, or a sensitizer and a sensitization auxiliary agent.

5. The curable composition according to claim 3 , comprising a coloring material.

6. The curable composition according to claim 3 , comprising a dispersing agent.

7. The curable composition according to claim 3 , wherein the curable composition is an ultraviolet-curable inkjet ink.

8. A method of producing a molded article comprising: ejecting the curable composition described in claim 7 using an inkjet method, then curing the ejected curable composition, and forming a molded article from a cured product of the curable composition.

9. The curable composition according to claim 3 , wherein the curable composition is a coating agent.

10. The curable composition according to claim 3 , wherein the curable composition is an adhesive agent.

11. A cured product of the curable composition described in claim 3 .

12. A molded article formed from the cured product described in claim 11 .

13. A structure comprising the cured product described in claim 11 on a substrate surface.

Assignees

• Daicel Corp

Inventors

• Mizuta Tomoya
• Inoue Keizo

Classifications

• C08F216/1416

  Monomers containing oxygen in addition to the ether oxygen, e.g. allyl glycidyl ether · CPC title

• B33Y10/00

  Processes of additive manufacturing · CPC title

• B41M5/00

  Duplicating or marking methods; Sheet materials for use therein (by using light-sensitive materials G03; electrography, magnetography G03G {; repeatedly usable boards or tablets for writing or drawing B43L1/00}) · CPC title

• C08G65/18

  Oxetanes · CPC title

• C09J4/00

  Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16} · CPC title