# US 12,180,320 B2 · Ultraviolet curable silicone composition and cured product thereof

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- Number: US 12,180,320 B2
- Document ID: US12180320B2
- Status: Granted
- Kind: B2
- Application number: 18/399,857
- Filed: 2023-12-29
- Published: 2024-04-25
- Granted: 2024-12-31
- Earliest claimed: 2018-09-20
- Assignees: Shin-Etsu Chemical Co., Ltd.
- Applicants: Shin-Etsu Chemical Co., Ltd.
- Inventors: Nobuaki Matsumoto; Kohei Otake; Taichi Kitagawa; Tsuyoshi Matsuda; Toshiyuki Ozai
- Web page: https://patentgrep.com/patent/US12180320B2

## CPC

- C08F 283/124: {on to polysiloxanes having carbon-to-carbon double bonds}
- C08F 290/068: {Polysiloxanes}
- C08L 83/04: Polysiloxanes
- B33Y 70/00: Materials specially adapted for additive manufacturing
- C08G 77/20: containing silicon bound to unsaturated aliphatic groups
- C08G 77/38: Polysiloxanes modified by chemical after-treatment
- C08G 77/50: by carbon linkages
- C08G 77/52: containing aromatic rings
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- 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
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

Provided are a low-viscosity ultraviolet curable silicone composition capable of being used even in a surface exposure method and a lift-up method etc.; and a cured product superior in tensile strength and elongation at break. The ultraviolet curable silicone composition contains: (A) an organopolysiloxane; (B) a photopolymerization initiator; and (C) a monofunctional (meth)acrylate compound having no siloxane structure and/or (D) a multifunctional (meth)acrylate compound having no siloxane structure, wherein the organopolysiloxane is represented by the following general formula (1): wherein n satisfies 1≤n≤1,000, m satisfies 1≤m≤1,000, Ar is an aromatic group, R1 represents a monovalent hydrocarbon group having 1 to 20 carbon atoms, A is a group represented by the following formula (2): wherein p satisfies 0≤p≤10, a satisfies 1≤a≤3, R1 represents a monovalent hydrocarbon group having 1 to 20 carbon atoms, R2 represents an oxygen atom or an alkylene group, R3 represents an acryloyloxyalkyl group or the like.

## Claims

### Claim 1

A method for producing a molding material by inkjet methods using 3D printers, comprising:
ejecting an ultraviolet curable silicone composition via ink-jet ejection using the ink-jet 3D printer to produce the molding material,
wherein an ultraviolet curable silicone composition is used as a 3D printer ink, the ultraviolet curable silicone composition comprising:
(A) 100 parts by mass of an organopolysiloxane;
(B) 0.1 to 10 parts by mass of a photopolymerization initiator; and
1 to 400 parts by mass of at least one of (C) a monofunctional (meth)acrylate compound having no siloxane structure and (D) a multifunctional (meth)acrylate compound having no siloxane structure, wherein the organopolysiloxane is represented by the following general formula (1):
wherein n is a number satisfying 1≤n≤1,000, m is a number satisfying 1≤m≤1,000, siloxane units identified by n and m are sequenced in any order, Ar is an aromatic group, each R1 independently represents a monovalent hydrocarbon group having 1 to 20 carbon atoms, A is a group represented by the following formula (2):
wherein p is a number satisfying 0≤p≤10, a is a number satisfying 1≤a≤3, each R1 independently represents an alkyl group having 1 to 10 carbon atoms, R2 represents an oxygen atom or an alkylene group, R3 represents an acryloyloxyalkyl group, a methacryloyloxyalkyl group, an acryloyloxyalkyloxy group or a methacryloyloxyalkyloxy group.

### Claim 2 (depends on 1)

The method for producing a molding material according to claim 1, wherein the ultraviolet curable silicone composition has a viscosity of not higher than 10,000 mPa·s at 25° C.

### Claim 3

A method for forming a molded product from an ultraviolet curable silicone composition by inkjet methods using ink-jet 3D printers, comprising:
ejecting the ultraviolet curable silicone composition via ink-jet ejection using the ink-jet 3D printer to produce the molded product,
wherein the ultraviolet curable silicone composition is used as a 3D printer ink, the ultraviolet curable silicone composition comprising:
(A) 100 parts by mass of an organopolysiloxane;
(B) 0.1 to 10 parts by mass of a photopolymerization initiator; and
1 to 400 parts by mass of at least one of (C) a monofunctional (meth)acrylate compound having no siloxane structure and (D) a multifunctional (meth)acrylate compound having no siloxane structure, wherein the organopolysiloxane is represented by the following general formula (1):
wherein n is a number satisfying 1≤n≤1,000, m is a number satisfying 1≤m≤1,000, siloxane units identified by n and m are sequenced in any order, Ar is an aromatic group, each R1 independently represents a monovalent hydrocarbon group having 1 to 20 carbon atoms, A is a group represented by the following formula (2):
wherein p is a number satisfying 0≤p≤10, a is a number satisfying 1≤a≤3, each R1 independently represents an alkyl group having 1 to 10 carbon atoms, R2 represents an oxygen atom or an alkylene group, R3 represents an acryloyloxyalkyl group, a methacryloyloxyalkyl group, an acryloyloxyalkyloxy group or a methacryloyloxyalkyloxy group.

### Claim 4

A method for applying an ultraviolet curable silicone composition to form a molded product by inkjet methods using ink-jet 3D printers, comprising:
ejecting the ultraviolet curable silicone composition via ink-jet ejection using the ink-jet 3D printer to produce the molded product,
wherein the ultraviolet curable silicone composition is used as a 3D printer ink, the ultraviolet curable silicone composition comprising:
(A) 100 parts by mass of an organopolysiloxane;
(B) 0.1 to 10 parts by mass of a photopolymerization initiator; and
1 to 400 parts by mass of at least one of (C) a monofunctional (meth)acrylate compound having no siloxane structure and (D) a multifunctional (meth)acrylate compound having no siloxane structure, wherein the organopolysiloxane is represented by the following general formula (1):
wherein n is a number satisfying 1≤n≤1,000, m is a number satisfying 1≤m≤1,000, siloxane units identified by n and m are sequenced in any order, Ar is an aromatic group, each R1 independently represents a monovalent hydrocarbon group having 1 to 20 carbon atoms, A is a group represented by the following formula (2):
wherein p is a number satisfying 0≤p≤10, a is a number satisfying 1≤a≤3, each R1 independently represents an alkyl group having 1 to 10 carbon atoms, R2 represents an oxygen atom or an alkylene group, R3 represents an acryloyloxyalkyl group, a methacryloyloxyalkyl group, an acryloyloxyalkyloxy group or a methacryloyloxyalkyloxy group.