# US 11,306,230 B2 · Ultraviolet curable silicone adhesive composition and silicone adhesive film

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- Number: US 11,306,230 B2
- Document ID: US11306230B2
- Status: Granted
- Kind: B2
- Application number: 16/619,429
- Filed: 2018-06-12
- Published: 2020-06-04
- Granted: 2022-04-19
- Earliest claimed: 2017-07-05
- Assignees: Shin-Etsu Chemical Co., Ltd.
- Applicants: Shin-Etsu Chemical Co., Ltd.
- Inventors: Tsuyoshi Matsuda; Ken Nakayama
- Web page: https://patentgrep.com/patent/US11306230B2

## CPC

- C09J 183/04: Polysiloxanes
- B32B 27/00: Layered products comprising {a layer of} synthetic resin {(fibrous or filamentary layer made of a synthetic resin B32B5/02; particulate layer made of a synthetic resin B32B5/16; foamed layer made of a synthetic resin B32B5/18)}
- C08F 290/06: Polymers provided for in subclass C08G
- C08G 77/18: to alkoxy or aryloxy groups
- C08G 77/20: containing silicon bound to unsaturated aliphatic groups
- C08G 77/70: {Siloxanes defined by use of the MDTQ nomenclature}
- C08G 77/80: {Siloxanes having aromatic substituents, e.g. phenyl side groups}
- C08K 5/14: Peroxides
- C08K 5/5415: containing at least one Si—O bond
- C08K 5/5425: containing at least one C=C bond
- C08L 83/06: containing silicon bound to oxygen-containing groups (C08L83/12 takes precedence)
- C09D 183/06: containing silicon bound to oxygen-containing groups (C09D183/12 takes precedence)
- C09J 7/25: based on macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
- C09J 7/38: Pressure-sensitive adhesives [PSA]
- C09J 183/06: containing silicon bound to oxygen-containing groups (C09J183/12 takes precedence)
- C09J 183/10: Block or graft copolymers containing polysiloxane sequences (obtained by polymerising a compound having a carbon-to-carbon double bond on to a polysiloxane C09J151/08, C09J153/00)
- C09J 2203/318: for the production of liquid crystal displays
- C09J 2203/326: for bonding electronic components such as wafers, chips or semiconductors
- C09J 2301/12: by the arrangement of layers
- C09J 2301/416: use of irradiation
- C09J 2483/00: Presence of polysiloxane
- Y10T 428/31504: Composite [nonstructural laminate]
- Y10T 428/31663: As siloxane, silicone or silane
- 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)
- B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- 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)
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

This ultraviolet curable silicone adhesive composition that contains (A) an organopolysiloxane resin which contains (a) an R13SiO1/2 unit (wherein R1 represents a monovalent hydrocarbon group) and (b) an SiO4/2 unit, and wherein the molar ratio of the unit (a) to the unit (b) is from 0.6:1 to 1.2:1, (B) a linear or branched organopolysiloxane which has a viscosity of more than 50 mPa·s but 500,000 mPa·s or less, while having 1-4 groups represented by formula (1) and/or (2) (wherein R2 represents H or Me, a represents a number of 1-3, and the broken line represents a bonding hand that is bonded with Si) as Si-bonded groups, and wherein the main chain is composed of repeated diorganosiloxane units, and (C) a reactive diluent which is composed of an organo(poly)siloxane that has a viscosity of 1-50 mPa·s, while having one group represented by formula (3) (wherein a is as defined above, and the broken line represents a bonding hand) at an end of the molecular chain or in a molecular side chain as an Si-bonded group, is rapidly cured by means of irradiation of ultraviolet light, and exhibits good adhesion to a sheet-like substrate.

## Claims

### Claim 1

A UV-curable silicone pressure-sensitive adhesive composition comprising
(A) 30 to 70 parts by weight of an organopolysiloxane resin (A) comprising (a) R13SiO1/2 units wherein R1 is a substituted or unsubstituted C1-C10 monovalent hydrocarbon group and (b) SiO4/2 units, wherein a molar ratio of units (a) to units (b) is from 0.6:1 to 1.2:1,
(B) 1 to 40 parts by weight of a linear or branched organopolysiloxane (B) having a backbone composed of repeating diorganosiloxane units and containing an average of 1 to 4 monovalent substituent groups per molecule, the monovalent substituent groups having the general formula (4):
wherein R2 is hydrogen or methyl, R3 is independently a substituted or unsubstituted C1-C10 monovalent hydrocarbon group, X is a C2-C6 alkylene group, a is an integer of 1 to 3, b is 1 or 2, and the broken line designates a valence bond to a silicon atom,
the organopolysiloxane (B) having a viscosity at 25° C. of from more than 50 mPa·s to 500,000 mPa·s, and
(C) 1 to 40 parts by weight of a reactive diluent, the reactive diluent being an organopolysiloxane (C) containing one monovalent group having the general formula (3):
wherein a is as defined above and the broken line designates a valence bond to a silicon atom at an end or on a side chain of the organopolysiloxane (C) molecular chain, the organopolysiloxane (C) having a viscosity at 25° C. of 1 to 50 mPa·s,
with the proviso that the total amount of organopolysiloxane resin (A), organopolysiloxane (B), and organopolysiloxane (C) is 100 parts by weight.

### Claim 2 (depends on 1)

The silicone pressure-sensitive adhesive composition of claim 1 wherein the organopolysiloxane (B) contains monovalent substituent groups having the general formula (4) at both ends of the molecular chain.

### Claim 3 (depends on 1, 2)

The silicone pressure-sensitive adhesive composition of claim 1 or 2 wherein the backbone of the organopolysiloxane (B) consists of diphenylsiloxane repeating units having the general formula (6):
wherein Me is methyl, Ph is phenyl, c1 and c2 are integers in the range: c1≥0, c2≥1, and c1+c2=c, c is such a number that the organopolysiloxane (B) has a viscosity at 25° C. of from more than 50 mPa·s to 500,000 mPa·s, and the broken line designates a valence bond.

### Claim 4 (depends on 1)

The silicone pressure-sensitive adhesive composition of claim 1 wherein the organopolysiloxane (C) has the general formula (7) or (8):
wherein R6 to R10 each are a substituted or unsubstituted C1-C12 monovalent hydrocarbon group, a is an integer of 1 to 3, the organo(poly)siloxane has a viscosity at 25° C. of 1 to 50 mPa·s, d is an integer of 0 to 3, e and f are 0 or 1.

### Claim 5 (depends on 1)

The silicone pressure-sensitive adhesive composition of claim 1, further comprising (D) 0.01 to 15 parts by weight of a photo-initiator per 100 parts by weight of the organopolysiloxane resin (A), the organopolysiloxane (B), and the organopolysiloxane (C) combined.

### Claim 6 (depends on 1)

The silicone pressure-sensitive adhesive composition of claim 1 which forms a silicone pressure-sensitive adhesive having a storage elastic modulus of up to 1.0 MPa after curing, wherein the storage elastic modulus is measured at 1.0 Hz, an oscillation angle γ 4.0%, and a temperature of 25±0.5° C.

### Claim 7 (depends on 1)

A silicone pressure-sensitive adhesive film comprising a substrate and a pressure-sensitive adhesive layer formed on at least one surface of the substrate, said pressure-sensitive adhesive layer being a UV-cured product of the silicone pressure-sensitive adhesive composition of claim 1.

### Claim 8 (depends on 7)

The silicone pressure-sensitive adhesive film of claim 7 wherein the substrate is a plastic film.