# US 2022/0033554 A1 · Photocurable resin composition

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- Number: US 2022/0033554 A1
- Document ID: US20220033554A1
- Status: Published application
- Kind: A1
- Application number: 17/387,853
- Filed: 2021-07-28
- Published: 2022-02-03
- Earliest claimed: 2020-07-31
- Assignees: Canon Kabushiki Kaisha
- Applicants: Canon Kabushiki Kaisha
- Inventors: Emi Oishi
- Web page: https://patentgrep.com/patent/US20220033554A1

## CPC

- C08F 220/281: {and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate}
- B29C 64/129: characterised by the energy source therefor, e.g. by global irradiation combined with a mask
- B29C 64/135: the energy source being concentrated, e.g. scanning lasers or focused light sources
- B33Y 70/00: Materials specially adapted for additive manufacturing
- C08F 222/102: {of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate}
- C08F 222/103: {of trialcohols, e.g. trimethylolpropane tri(meth)acrylate}
- C08F 222/20: Esters containing oxygen in addition to the carboxy oxygen
- C08K 5/5397: Phosphine oxides
- C09D 133/064: {containing anhydride, COOH or COOM groups, with M being metal or onium-cation}
- C09D 133/14: of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
- B33Y 10/00: Processes of additive manufacturing
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- B29C: SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING (making preforms B29B11/00; making laminated products by combining previously unconnected layers which become one product whose layers will remain together B32B37/00 - B32B41/00)
- B33Y: ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- 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

A curable resin composition which provides a cured product excellent in impact resistance and flexural modulus and has a low viscosity comprising a component (A), a component (B) and a component (C). The component (A) is a compound represented by formula (1), wherein in formula (1), R is hydrogen or a hydrocarbon group having 1 to 4 carbon atoms, and the hydrocarbon group optionally has a substituent, wherein the component (B) is a compound having 3 or more to 15 or less of oxyethylene groups or oxypropylene groups and two or more radically polymerizable groups per molecule, and wherein the component (C) is a radical polymerization initiator.

## Claims

### Claim 1

A photocurable resin composition comprising:
a component (A);
a component (B); and
a component (C),
wherein the component (A) is a compound represented by formula (1)
wherein in formula (1), R is hydrogen or a hydrocarbon group having 1 to 4 carbon atoms, and the hydrocarbon group optionally has a substituent,
wherein the component (B) is a compound having 3 or more to 15 or less of oxyethylene groups or oxypropylene groups and two or more radically polymerizable groups per molecule,
wherein the component (C) is a radical polymerization initiator,
wherein X, the number of oxyethylene groups or oxypropylene groups in the photocurable resin composition, is calculated by the following formula (i),
wherein Y, the number of crosslinking groups in the photocurable resin composition, is calculated by the following formula (ii):
X=xBnB/(xA+xBnB+xBmB)×100 (i)
Y=xBmB/(xA+xBnB+xBmB)×100 (ii),
wherein xA is mole fraction of the component (A),
wherein xB is mole fraction of the component (B),
wherein nB is the number of oxyethylene groups or oxypropylene groups per molecule of the component (B),
wherein mB is the number of radically polymerizable groups per molecule of the component (B), and
wherein X is 30 to 45 inclusive and Y is 10 to 19 inclusive.

### Claim 2 (depends on 1)

The photocurable resin composition according to claim 1, wherein the content of the component (A) is 60 mass % or more and 80 mass % or less.

### Claim 3 (depends on 1)

The photocurable resin composition according to claim 1, wherein the content of the component (A) is 65 mass % or more and 75 mass % or less.

### Claim 4 (depends on 1)

The photocurable resin composition according to claim 1, wherein a viscosity of the photocurable resin composition is 100 cps or less.

### Claim 5 (depends on 1)

The photocurable resin composition according to claim 1, wherein the component (B) has 6 or more to 14 or less of oxyethylene groups or oxypropylene groups.

### Claim 6 (depends on 1)

The photocurable resin composition according to claim 1, wherein the component (B) comprises a group having a carbon-carbon double bond as the radical polymerizable group.

### Claim 7 (depends on 6)

The photocurable resin composition according to claim 6, wherein the group having the carbon-carbon double bond is an acryloyl group or a methacryloyl group.

### Claim 8

A photocurable resin composition comprising:
a component (A);
a component (B);
a component (C); and
a component (D),
wherein the component (A) is a compound represented by formula (1),
wherein in formula (1), R is hydrogen or a hydrocarbon group having 1 to 4 carbon atoms, and the hydrocarbon group optionally has a substituent,
wherein the component (B) is a compound having 3 or more and 15 or less of oxyethylene groups or oxypropylene groups and two or more radically polymerizable groups per molecule,
wherein the component (C) is a radical polymerization initiator,
wherein the component (D) is a polyfunctional radically polymerizable compound which is different from the component (B),
wherein X, the number of oxyethylene groups or oxypropylene groups in the photocurable resin composition, is calculated by the following formula (iii),
wherein Y, the number of crosslinking groups in the photocurable resin composition, is calculated by the following formula (iv):
X=xBnB/(xA+xBnB+xBmB+xDmD)×100 (iii)
Y=xBmB+xDmD/(xA+xBnB+xBmB+xDmD)×100 (iv),
wherein xA is mole fraction of the component (A),
wherein xB is mole fraction of the component (B),
wherein xD is mole fraction of the component (D),
wherein nB is the number of oxyethylene groups or oxypropylene groups per molecule of the component (B),
wherein mB is the number of radically polymerizable groups per molecule of the component (B),
wherein mD is the number of radically polymerizable groups per molecule of the component (D), and
wherein X is 30 to 45 inclusive and Y is 10 to 19 inclusive.

### Claim 9 (depends on 8)

The photocurable resin composition according to claim 8, wherein the content of the component (A) is 60 mass % or more and less than 80 mass %.

### Claim 10 (depends on 8)

The photocurable resin composition according to claim 8, wherein the content of the component (A) is 65 mass % or more and less than 75 mass %.

### Claim 11 (depends on 8)

The photocurable resin composition according to claim 8, wherein a viscosity of the photocurable resin composition is 100 cps or less.

### Claim 12 (depends on 8)

The photocurable resin composition according to claim 8, wherein the component (B) has 6 or more to 14 or less of oxyethylene groups or oxypropylene groups.

### Claim 13 (depends on 8)

The photocurable resin composition according to claim 8, wherein the component (B) comprises a group having a carbon-carbon double bond as the radical polymerizable group.

### Claim 14 (depends on 13)

The photocurable resin composition according to claim 13, wherein the group having the carbon-carbon double bond is an acryloyl group.

### Claim 15 (depends on 1)

A cured product obtained by curing the photocurable resin composition according to claim 1.

### Claim 16 (depends on 8)

A cured product obtained by curing the photocurable resin composition according to claim 8.

### Claim 17

A method for producing an article comprising:
repeating a step of forming a cured layer by photocuring a photocurable resin composition with a predetermined thickness is multiple times,
wherein the photocurable resin composition comprises a component (A), a component (B) and a component (C),
wherein the component (A) is a compound represented by formula (1)
wherein in formula (1), R is hydrogen or a hydrocarbon group having 1 to 4 carbon atoms, and the hydrocarbon group optionally has a substituent,
wherein the component (B) is a compound having 3 or more to 15 or less of oxyethylene groups or oxypropylene groups and two or more radically polymerizable groups per molecule,
wherein the component (C) is a radical polymerization initiator,
wherein the number of oxyethylene groups or oxypropylene groups in the photocurable resin composition, is calculated by the following formula (i),
wherein Y, the number of crosslinking groups in the photocurable resin composition, is calculated by the following formula (ii):
X=xBnB/(xA+xBnB+xBmB)×100 (i)
Y=xBmB/(xA+xBnB+xBmB)×100 (ii),
wherein xA is mole fraction of the component (A),
wherein xB is mole fraction of the component (B),
wherein nB is the number of oxyethylene groups or oxypropylene groups per molecule of the component (B),
wherein mB is the number of radically polymerizable groups per molecule of the component (B), and
wherein X is 30 to 45 inclusive and Y is 10 to 19 inclusive.

### Claim 18 (depends on 17)

The method of manufacturing an article according to claim 17, wherein said method comprises:
disposing the curable resin composition at a predetermined thickness; and
curing the curable resin composition by irradiating the curable resin composition with light energy based on a slice data of a three-dimensional model.

### Claim 19

A method for producing an article comprising:
repeating, for plural times, a step of forming a cured layer by photocuring a photocurable resin composition with a predetermined thickness, and
wherein the photocurable resin composition comprises a component (A), a component (B), a component (C) and a component (D),
wherein the component (A) is a compound represented by formula (1),
wherein in formula (1), R is hydrogen or a hydrocarbon group having 1 to 4 carbon atoms and, the hydrocarbon group optionally has a substituent,
wherein the component (B) is a compound having 3 or more and 15 or less of oxyethylene groups or oxypropylene groups and two or more radically polymerizable groups per molecule,
wherein the component (C) is a radical polymerization initiator,
wherein the component (D) is a polyfunctional radically polymerizable compound which is different from the component (B),
wherein X, the number of oxyethylene groups or oxypropylene groups in the photocurable resin composition, is calculated by the following formula (iii),
wherein Y, the number of crosslinking groups in the photocurable resin composition, is calculated by the following formula (iv):
X=xBnB/(xA+xBnB+xBmB+xDmD)×100 (iii)
Y=xBmB+xDmD/(xA+xBnB+xBmB+xDmD)×100 (iv),
wherein xA is mole fraction of the component (A),
wherein xB is mole fraction of the component (B),
wherein xD is mole fraction of the component (D),
wherein nB is the number of oxyethylene groups or oxypropylene groups per molecule of the component (B),
wherein mB is the number of radically polymerizable groups per molecule of the component (B),
wherein mD is the number of radically polymerizable groups per molecule of the component (D), and
wherein X is 30 to 45 inclusive and Y is 10 to 19 inclusive.

### Claim 20 (depends on 19)

The method of manufacturing an article according to claim 19, wherein said method comprises:
disposing the curable resin composition at a predetermined thickness; and
curing the curable resin composition by irradiating the curable resin composition with light energy based on a slice data of a three-dimensional model.