# US 11,028,224 B2 · Monomer mixture and curable composition containing same

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- Number: US 11,028,224 B2
- Document ID: US11028224B2
- Status: Granted
- Kind: B2
- Application number: 16/622,222
- Filed: 2019-01-25
- Published: 2020-12-03
- Granted: 2021-06-08
- Earliest claimed: 2018-02-05
- Assignees: Daicel Corporation
- Applicants: Daicel Corporation
- Inventors: Tomoya Mizuta; Keizo Inoue
- Web page: https://patentgrep.com/patent/US11028224B2

## CPC

- C08G 65/18: Oxetanes
- C09D 11/101: Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
- C08F 16/32: Monomers containing two or more unsaturated aliphatic radicals
- C08G 59/24: carbocyclic
- C09D 11/322: Pigment inks
- C09J 171/02: Polyalkylene oxides
- C08F 16/26: Monomers containing oxygen atoms in addition to the ether oxygen
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)

## Abstract

The present invention provides a monomer mixture that rapidly cures even in high humidity environments, and is useful as a raw material for a curable composition that forms a cured product having excellent adhesion to metals and glass, as well as of course to paper and plastic. The monomer mixture according to an embodiment of the present invention contains two or more types of cationically polymerizable monomers. The monomer mixture contains, as the cationically polymerizable monomers, a compound (A) having a vinyl ether group and a hydroxyl group; a compound (B) having an oxetanyl group and a hydroxyl group; and a compound (C) represented by Formula (c) below. A total content of the compound (A), the compound (B), and the compound (C) is 50 wt. % or greater of the total amount of the monomer mixture, and a content [A] of the compound (A) and a content [B] of the compound (B) satisfy Relationship (1) below. A/(A+B)≥0.3 (1)

## Claims

### Claim 1

A monomer mixture comprising two or more types of cationically polymerizable monomers, the monomer mixture comprising, as the cationically polymerizable monomers: a compound (A) having one vinyl ether group and one hydroxyl group; a compound (B) having one oxetanyl group and one hydroxyl group; a compound (C) represented by Formula (c):
where X denotes a single bond or a linking group; and a compound (E) having two or more oxetanyl groups, excluding a compound having a hydroxyl group;
wherein a total content of the compound (A), the compound (B), and the compound (C) is 50 wt. % or greater of the total amount of the monomer mixture, and a content [A] of the compound (A) and a content [B] of the compound (B) satisfy Relationship (1);
A/(A+B)≥0.3 (1)
and the content of the compound (E) being from 15 to 40 wt. % of the total amount of the monomer mixture
and the content [B] of the compound (B) being from 1 to 15 wt. % of the total amount of the monomer mixture.

### Claim 2 (depends on 1)

The monomer mixture according to claim 1, further comprising, as a cationically polymerizable monomer, a compound (D) having two or more vinyl ether groups bonded to an alicyclic skeleton or a non-aromatic heterocyclic skeleton, excluding a compound having a hydroxyl group, the content of the compound (D) being from 1 to 10 wt. % of the total amount of the monomer mixture.

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 3)

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

### Claim 5 (depends on 3)

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

### Claim 6 (depends on 3)

The curable composition according to claim 3, comprising a dispersant.

### Claim 7 (depends on 3)

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

### Claim 8 (depends on 3)

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

### Claim 9 (depends on 3)

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

### Claim 10 (depends on 8)

A cured product described in claim 8, wherein adhesion to a paper substrate, a plastic substrate, a metal substrate, and a glass substrate is rated grade 0 to 2 in a 6-grade classification test through a cross-cut method in accordance with JIS K 5600-5-6.

### Claim 11 (depends on 9)

A molded article comprising the cured product described in claim 9.

### Claim 12 (depends on 9)

A structure comprising the cured product described in claim 9 on a substrate surface.