KR-20260066048-A - UV-curable silicone composition and the cured product thereof

Abstract

(A) A polysiloxane having the unit of Formula (1) (where R1 is a monovalent hydrocarbon group, R2 is an oxygen atom, etc., R3 is an acryloyloxyalkyl group, etc., p is 0≤p≤10, and a is 1≤a≤3) and the unit of (b) R1 Rf1 SiO2 /2 (where R1 is the same as above, and Rf1 is a fluoroalkyl group having 1 to 8 carbon atoms), wherein 5% or more of the monovalent organic groups on Si are the fluoroalkyl groups; (B) (c) A polysiloxane having the unit of Formula (2) or Formula (2') (where R6 is a monovalent hydrocarbon group, R7 is an oxygen atom, etc., R8 is an acryloyloxyalkyl group, etc., q is 0≤q≤10, and c is 1≤c≤3) and the unit of (d) Rf2 SiO3 / 2 (where Rf2 is A silicone composition containing a polysiloxane resin (C) photopolymerization initiator having a unit of 1 to 8 carbon fluoroalkyl groups and having 5% or more of the monovalent organic groups on Si as CF3 , rapidly cures upon UV irradiation to provide a cured product having release properties.

Inventors

• 사카모토 아키라
• 마츠모토 노부아키
• 코바야시 유키토
• 오자이 토시유키
• 오가와 요시노리

Assignees

• 신에쓰 가가꾸 고교 가부시끼가이샤

Dates

Publication Date

20260512

Application Date

20240724

Priority Date

20230914

Claims (4)

1. (A)(a) General formula (1) (In the formula, R1 independently represents a monovalent hydrocarbon group having 1 to 20 carbon atoms, R2 represents an oxygen atom or an alkylene group having 1 to 20 carbon atoms, R3 independently represents an acryloyloxyalkyl group, a methacryloyloxyalkyl group, an acryloyloxyalkyloxy group, or a methacryloyloxyalkyloxy group, p represents a number satisfying 0 ≤ p ≤ 10, and a represents a number satisfying 1 ≤ a ≤ 3.) Units indicated as, and (b) Organopolysiloxane having a unit represented by R 1 Rf 1 SiO 2/2 (R 1 has the same meaning as above, and Rf 1 represents a fluorine-substituted alkyl group having 1 to 8 carbon atoms bonded to a silicon atom), wherein at least 5% of the total number of monovalent organic groups bonded to a silicon atom is a fluorine-substituted alkyl group having 1 to 8 carbon atoms: 100 parts by mass (B)(c) The following general formula (2) or the following general formula (2') A unit represented by (wherein R6 independently represents a monovalent hydrocarbon group having 1 to 20 carbon atoms, R7 represents an oxygen atom or an alkylene group having 1 to 20 carbon atoms, R8 independently represents an acryloyloxyalkyl group, a methacryloxyalkyl group, an acryloyloxyalkyloxy group, or a methacryloxyalkyloxy group, q represents a number satisfying 0≤q≤10, and c represents a number satisfying 1≤c≤3), and (d) an organopolysiloxane resin having a unit represented by Rf 2 SiO 3/2 (Rf 2 represents a fluorine-substituted alkyl group having 1 to 8 carbon atoms bonded to a silicon atom), wherein at least 5% of the total number of monovalent organic groups bonded to a silicon atom is a trifluoropropyl group: 1 to 1000 parts by mass, and (C) Photopolymerization initiator: 0.01 to 20 parts by mass UV-curable silicone composition containing
2. A UV-curable silicone composition according to claim 1, comprising 1 to 1,000 parts by mass of (D) a monofunctional (meth)acrylate compound not containing a siloxane structure per 100 parts by mass of component (A).
3. A cured product of the UV-curable silicone composition described in paragraph 1 or 2.
4. In paragraph 3, a hardened material having a Type D hardness of 30 or higher as specified in JIS K6253-3:2012.

Description

UV-curable silicone composition and the cured product thereof The present invention relates to a UV-curable silicone composition and a cured product thereof. For materials with fine patterns formed on their surfaces, such as lens materials for 3D sensors, imprint molding using a mold is common. In imprint molding, there are methods of forming the target material directly from the mold and methods of producing a replica mold from the mold and replicating the lens material from that replica mold; the latter is highly advantageous in terms of production efficiency. In this case, to improve yield, it is common practice to apply a release treatment to the surfaces of the mold and the replica mold material to prevent the lens material and the replica mold from adhering to each other, and thus, simplification of the release agent application process is desired. As such a material, a fluorine-containing acrylic resin material (Patent Document 1) is known. However, in the technology using this material, cleaning with a solvent or heating is required after molding the replica mold material, so simplification of the process was required. The present invention will be described in detail below. The UV-curable silicone composition according to the present invention is, (A) (a) an organopolysiloxane having a unit represented by the following general formula (1), and (b) an organopolysiloxane having a unit represented by R 1 Rf 1 SiO 2/2 (R 1 represents a monovalent hydrocarbon group having 1 to 20 carbon atoms, and Rf 1 represents a fluorine-substituted alkyl group having 1 to 8 carbon atoms bonded to a silicon atom): 100 parts by mass (B)(c) a unit represented by the following general formula (2), and (d) an organopolysiloxane resin comprising a unit represented by Rf 2 SiO 3/2 (Rf 2 represents a fluorine-substituted alkyl group having 1 to 8 carbon atoms bonded to a silicon atom), wherein at least 5% of the total number of monovalent organic groups bonded to a silicon atom is a trifluoropropyl group: 1 to 1000 parts by mass, and (C) Photopolymerization initiator: Characterized by containing 0.01 to 20 parts by mass. (A) Organopolysiloxane The component (A) used in the present invention is a crosslinking component of the present composition and is an organopolysiloxane having a siloxane unit represented by (a) the general formula (1) below and (b) a siloxane unit represented by R 1 Rf 1 SiO 2/2 , wherein the main chain is substantially composed of repeating diorganosiloxane units. In formula (1), R1 independently represents a monovalent hydrocarbon group having 1 to 20 carbon atoms, preferably excluding an aliphatic unsaturated group, having 1 to 10 carbon atoms, more preferably having 1 to 8 carbon atoms; R2 represents an oxygen atom or an alkylene group having 1 to 20 carbon atoms, preferably having 1 to 10 carbon atoms, more preferably having 1 to 5 carbon atoms; and R3 independently represents an acryloyloxyalkyl group, a methacryloxyalkyl group, an acryloyloxyalkyloxy group, or a methacryloxyalkyloxy group. In formula (1), the monovalent hydrocarbon group of R1 having 1 to 20 carbon atoms may be straight, branched, or cyclic, and specific examples thereof include alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-hexyl, cyclohexyl, n-octyl, 2-ethylhexyl, n-decyl; alkenyl groups such as vinyl, allyl (2-propenyl), 1-propenyl, isopropenyl, butenyl; aryl groups such as phenyl, tolyl, xylyl, naphthyl; and aralkyl groups such as benzyl, phenylethyl, and phenylpropyl. In addition, some or all of the hydrogen atoms bonded to the carbon atoms of these monovalent hydrocarbon groups may be substituted with other substituents, and specific examples thereof include halogen-substituted hydrocarbon groups such as chloromethyl, bromoethyl, trifluoropropyl, and cyanoethyl groups, or cyano-substituted hydrocarbon groups. Among these, as R1 , an alkyl group having 1 to 5 carbon atoms and a phenyl group are preferred, and a methyl group, an ethyl group, and a phenyl group are more preferred. Also, the alkylene group of R2 having 1 to 20 carbon atoms may be straight, branched, or cyclic, and specific examples include methylene, ethylene, propylene, trimethylene, tetramethylene, isobutylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, nonamethylene, decylene, etc. Among these, as R2 , an oxygen atom, methylene, ethylene, or trimethylene group is preferred, and an oxygen atom or an ethylene group is more preferred. In addition, the number of carbon atoms in the alkyl (alkylene) group of the acryloyloxyalkyl group, methacryloyloxyalkyl group, acryloyloxyalkyloxy group, or methacryloyloxyalkyloxy group of R3 is not particularly limited, but is preferably 1 to 10, and more preferably 1 to 5. Specific examples of these alkyl groups include those having 1 to 10 carbon atoms among the groups exemplified in R1 . Specific examples of R 3 include those represented by the following formulas,