# US 10,870,760 B2 · Epoxy group-containing organopolysiloxane, ultraviolet curable silicone composition, and method of forming a cured film

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- Number: US 10,870,760 B2
- Document ID: US10870760B2
- Status: Granted
- Kind: B2
- Application number: 16/341,096
- Filed: 2017-10-23
- Published: 2020-06-18
- Granted: 2020-12-22
- Earliest claimed: 2016-11-21
- Assignees: Shin-Etsu Chemical Co., Ltd.
- Applicants: Shin-Etsu Chemical Co., Ltd.
- Inventors: Ryota Hashimoto; Shinji Irifune
- Web page: https://patentgrep.com/patent/US10870760B2

## CPC

- C08L 83/06: containing silicon bound to oxygen-containing groups (C08L83/12 takes precedence)
- C08G 59/20: characterised by the epoxy compounds used
- C08G 59/68: characterised by the catalysts used
- C08G 77/12: containing silicon bound to hydrogen
- C08G 77/14: containing silicon bound to oxygen-containing groups
- C08G 77/38: Polysiloxanes modified by chemical after-treatment
- C09D 7/40: Additives
- C09D 183/06: containing silicon bound to oxygen-containing groups (C09D183/12 takes precedence)
- C08L 2201/10: Transparent films; Clear coatings; Transparent materials
- C08L 2203/16: used for films
- C08L 2312/04: with phenolic resin
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- 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)

## Abstract

An epoxy group-containing organopolysiloxane shows the following average composition formula (1) and has an epoxy equivalent of 500 g/mol or more. The epoxy group-containing organopolysiloxane has excellent ultraviolet curability even when the content of epoxy group is small (when the epoxy equivalent is large), an ultraviolet curable silicone composition uses the same, and a method forms a cured film. In the formula, each R1 represents the same or different unsubstituted or substituted monovalent hydrocarbon group having 1 to 10 carbon atoms (except for a group containing an epoxy group); R2 represents a group containing an epoxy group; R3 represents a hydrogen atom or a saturated monovalent hydrocarbon group having 1 to 4 carbon atoms; “a”, “b”, and “c” are positive numbers, “d” is 0 or a positive number, satisfying (a+b)/(c+d)=0.5 to 1.0.

## Claims

### Claim 1

An ultraviolet curable silicone composition, comprising
an onium salt photoinitiator that is configured to produce a cation species upon ultraviolet irradiation, and
an epoxy group-containing organopolysiloxane that is a solid at 25° C. and that has an epoxy equivalent of 500 g/mol or more, and a weight average molecular weight of 8000 or more, wherein the epoxy group-containing organopolysiloxane is shown by the following average composition formula (1):
where
each R1 represents the same or different unsubstituted or substituted monovalent hydrocarbon group having 1 to 10 carbon atoms (except for a group containing an epoxy group);
R2 represents a group containing an epoxy group;
R3 represents a hydrogen atom or a saturated monovalent hydrocarbon group having 1 to 4 carbon atoms;
“a”, “b”, “c”, and “d” are positive numbers, satisfying (a+b)/(c+d)=0.5 to 1.0.

### Claim 2 (depends on 1)

The ultraviolet curable silicone composition according to claim 1, wherein the epoxy group-containing organopolysiloxane is an addition reaction product of
(A) an organohydrogenpolysiloxane composed of an R13SiO1/2 unit, an R12HSiO1/2 unit, an SiO4/2 unit, and an R3OSiO3/2 unit, shown by the following average composition formula (2) and having an Si-H group content in a range of from 0.01 to 0.3 mol/100 g,
wherein R1, R3, “a”, “b”, “c”, and “d” have the same meanings as defined above; and
(B) a compound having both of an alkenyl group and an epoxy group.

### Claim 3 (depends on 2)

The ultraviolet curable silicone composition according to claim 2, wherein (A) the organohydrogenpolysiloxane has a weight average molecular weight of 6000 or more and a form of solid at 25° C.

### Claim 4 (depends on 1)

A method of forming a cured film, comprising applying the ultraviolet curable silicone composition according to claim 1 onto a substrate, and
performing ultraviolet irradiation to form a cured film.

### Claim 5 (depends on 2)

A method of forming a cured film, comprising
applying the ultraviolet curable silicone composition according to claim 2 onto a substrate, and
performing ultraviolet irradiation to form a cured film.

### Claim 6 (depends on 3)

A method of forming a cured film, comprising
applying the ultraviolet curable silicone composition according to claim 3 onto a substrate, and
performing ultraviolet irradiation to form a cured film.

### Claim 7 (depends on 1)

The ultraviolet curable silicone composition according to claim 1, further comprising another epoxy group-containing organopolysiloxane in addition to the epoxy group-containing organopolysiloxane represented by formula (1).

### Claim 8 (depends on 1)

The ultraviolet curable silicone composition according to claim 1, wherein the onium salt photoinitiator is selected from the group consisting of a diaryl iodonium salt, a triarylsulfonium salt, a triarylselenonium salt, a tetraarylphosphonium salt, and an aryldiazonium salt.

### Claim 9 (depends on 8)

The ultraviolet curable silicone composition according to claim 8, wherein an anion in the onium salt photoinitiator is selected from the group consisting of SbF6−, AsF6−, PF6−, BF4−, HSO4−, and ClO4−.

### Claim 10 (depends on 1)

The ultraviolet curable silicone composition according to claim 1, wherein an amount of the onium salt photoinitiator is in a range of from 0.1 to 20 parts by mass relative to 100 parts by mass of the ultraviolet curable silicone composition.

### Claim 11 (depends on 1)

The ultraviolet curable silicone composition according to claim 1, wherein “a”, “b”, “c”, and “d” satisfy (a+b)/(c+d)=0.6 to 0.9.

### Claim 12 (depends on 1)

The ultraviolet curable silicone composition according to claim 1, wherein R1 is a methyl group.

### Claim 13 (depends on 12)

The ultraviolet curable silicone composition according to claim 12, wherein R3 is a hydrogen atom.

### Claim 14 (depends on 2)

The ultraviolet curable silicone composition according to claim 2, wherein the Si—H group content is in a range of from 0.131 to 0.3 mol/100 g.