# US 12,110,426 B2 · Ultraviolet ray-curable silicone adhesive agent composition, and method for producing laminate

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- Number: US 12,110,426 B2
- Document ID: US12110426B2
- Status: Granted
- Kind: B2
- Application number: 17/425,100
- Filed: 2019-11-26
- Published: 2022-04-07
- Granted: 2024-10-08
- Earliest claimed: 2019-01-28
- Assignees: Shin-Etsu Chemical Co., Ltd.
- Applicants: Shin-Etsu Chemical Co., Ltd.
- Inventors: Takeharu Toyoshima; Atsushi Yaginuma; Toshiyuki Ozai
- Web page: https://patentgrep.com/patent/US12110426B2

## CPC

- C09J 183/04: Polysiloxanes
- C08G 77/08: characterised by the catalysts used
- C08G 77/12: containing silicon bound to hydrogen
- C08G 77/20: containing silicon bound to unsaturated aliphatic groups
- C08J 7/123: {Treatment by wave energy or particle radiation (C08J7/18 takes precedence)}
- C08G 77/045: {containing less than 25 silicon atoms}
- C08G 77/14: containing silicon bound to oxygen-containing groups
- C08G 77/70: {Siloxanes defined by use of the MDTQ nomenclature}
- C09J 2301/416: use of irradiation
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)

## Abstract

An ultraviolet ray-curable silicone adhesive agent composition comprising (A) a polysiloxane represented by formula (1): (R1SiO3/2)a1(R13SiO1/2)b1(X1O1/2)c1 (wherein R1 represents a monovalent hydrocarbon group wherein a methyl group accounts for 20 mol % or more and an alkenyl group accounts for 0.1 to 50 mol %; X1 represents a hydrogen atom or the like; a1 represents 0.1 to 1; b1 represents 0 to 0.75; and c1 represents 0 to 0.1; and the requirement represented by the formula: a1+b1+c1=1 is satisfied), (B) a polysiloxane represented by formula (2): (R23SiO1/2)a2(R22SiO)b2 (wherein R2 represents a monovalent hydrocarbon group wherein a methyl group accounts for 20 mol % or more and an alkenyl group accounts for 0.01 to 25 mol %; a2 represents 0.001 to 0.67; b2 represents 0.33 to 0.999; and the requirement represented by the formula: a2+b2=1 is satisfied), (C) a hydrogen polysiloxane represented by formula (3): R3dHeSiO[(4-d-e)/2] (wherein R3 represents a monovalent hydrocarbon group; and d and e represent numerical values satisfying the requirements represented by the formulae: 0.7≤d≤2.5, 0.01≤e≤1.0 and 0.8≤d+e≤2.7) and (D) a platinum-group catalyst capable of being activated with light having a wavelength of 200 to 500 nm. The ultraviolet ray-curable silicone adhesive agent composition can provide a cured article having excellent adhesion force to an object of interest even when being cured under room temperature.

## Claims

### Claim 1

An ultraviolet-curable silicone composition comprising:
(A) a branched organopolysiloxane represented by average unit formula (1) below
(R1SiO3/2)a1(R13SiO1/2)b1(X1O1/2)c1 (1)
wherein each R1 is independently a substituted or unsubstituted monovalent hydrocarbon group, with at least 80 mol % of the occurrences of R1 being methyl groups and the balance being vinyl groups; X1 is a hydrogen atom or an alkyl group, a1 is a number from 0.1 to 1, b1 is a number from 0 to 0.75, c1 is a number from 0 to 0.1, and a1+b1+c1=1;
(B) a linear organopolysiloxane represented by average unit formula (2) below
(R23SiO1/2)a2(R22SiO)b2 (2)
each R2 is independently a substituted or unsubstituted monovalent hydrocarbon group, with at least 20 mol % of the occurrences of R2 being methyl groups and from 0.01 to 25 mol % being alkenyl groups; a2 is a number from 0.001 to 0.67, b2 is a number from 0.33 to 0.999; and a2+b2=1 in an amount of from 0 to 5,000 parts by weight per 100 parts by weight of component (A);
(C) an organohydrogenpolysiloxane of average compositional formula (3) below that has at least two Si—H groups per molecule
R3dHeSiO[(4-d-e)/2] (3)
wherein each R3 is independently a substituted or unsubstituted monovalent hydrocarbon group exclusive of aliphatic unsaturated hydrocarbon groups, and ‘d’ and ‘e’ are numbers which satisfy the conditions 0.7≤d≤2.5, 0.01≤e≤1.0 and 0.8≤d+e≤2.7 in an amount such that the molar ratio of hydrosilyl groups included in component (C) to alkenyl groups included in components (A) and (B), expressed as hydrosilyl/alkenyl, is from 0.8 to 2.0; and
(D) a platinum metal catalyst that is activated by light having a wavelength of between 200 and 500 nm.

### Claim 2 (depends on 1)

The ultraviolet-curable silicone composition of claim 1, wherein R1 is a monovalent hydrocarbon group of 1 to 3 carbon atoms.

### Claim 3 (depends on 1)

The ultraviolet-curable silicone adhesive composition of claim 1, wherein component (D) is an (η5-cyclopentadienyl)tri(aliphatic)platinum compound or a bis(β-diketonato)platinum compound.

### Claim 4 (depends on 1)

The ultraviolet-curable silicone adhesive composition of claim 1, further comprising (E) a compound having at least one moiety selected from the group consisting of (meth)acrylic, carbonyl, epoxy, alkoxysilyl and amide moieties per molecule.

### Claim 5 (depends on 1)

A method for producing a laminated body which has a first substrate, a second substrate superimposed on the first substrate and an intervening adhesive layer obtained using the adhesive composition of claim 1, which method comprises the steps of:
coating the adhesive composition onto a surface of the first substrate;
irradiating the adhesive composition with ultraviolet light;
curing the adhesive composition to form an adhesive layer; and
superimposing the second substrate on the adhesive composition or adhesive layer and laminating together the first and second substrates through the adhesive composition or adhesive layer.