# US 11,028,225 B2 · Monomer mixture and curable composition containing same

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- Number: US 11,028,225 B2
- Document ID: US11028225B2
- Status: Granted
- Kind: B2
- Application number: 16/615,481
- Filed: 2018-07-19
- Published: 2020-06-25
- Granted: 2021-06-08
- Earliest claimed: 2017-07-28
- Assignees: Daicel Corporation
- Applicants: Daicel Corporation
- Inventors: Tomoya Mizuta; Keizo Inoue
- Web page: https://patentgrep.com/patent/US11028225B2

## CPC

- C08G 59/38: together with di-epoxy compounds
- C08G 65/26: from cyclic ethers and other compounds
- C08G 65/18: Oxetanes
- C08L 63/00: Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- 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
- C09D 11/30: Inkjet printing inks
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- 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)

## 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).

## Claims

### Claim 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.

### Claim 2 (depends on 1)

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.

### Claim 3 (depends on 1)

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.

### Claim 4 (depends on 1)

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

### Claim 5 (depends on 1)

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.

### Claim 6 (depends on 1)

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

### Claim 7 (depends on 6)

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

### Claim 8 (depends on 6)

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

### Claim 9 (depends on 6)

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

### Claim 10 (depends on 6)

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

### Claim 11 (depends on 10)

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.

### Claim 12 (depends on 6)

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

### Claim 13 (depends on 12)

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

### Claim 14 (depends on 12)

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

### Claim 15 (depends on 1)

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.

### Claim 16 (depends on 1)

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.

### Claim 17 (depends on 1)

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.

### Claim 18 (depends on 1)

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