# US 10,479,855 B2 · (Meth)acrylic copolymer, adhesive composition and adhesive sheet containing same, and coating material and coated product using same

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- Number: US 10,479,855 B2
- Document ID: US10479855B2
- Status: Granted
- Kind: B2
- Application number: 15/578,780
- Filed: 2016-06-01
- Published: 2018-05-24
- Granted: 2019-11-19
- Earliest claimed: 2015-06-02
- Assignees: Mitsubishi Chemical Corporation
- Applicants: Mitsubishi Chemical Corporation
- Inventors: Eri Masuda; Junichi Nakamura; Hiroko Shinada; Takayuki Kobayashi
- Web page: https://patentgrep.com/patent/US10479855B2

## CPC

- C08F 290/046: {Polymers of unsaturated carboxylic acids or derivatives thereof}
- C09D 151/003: {grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds (C09D151/04, C09D151/06 take precedence)}
- C09D 155/005: {Homopolymers or copolymers obtained by polymerisation of macromolecular compounds terminated by a carbon-to-carbon double bond}
- C09J 7/10: without carriers
- C09J 133/04: Homopolymers or copolymers of esters {(C09J143/04 takes precedence)}
- C09J 151/003: {grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds (C09J151/04, C09J151/06 take precedence)}
- C09J 155/005: {Homopolymers or copolymers obtained by polymerisation of macromolecular compounds terminated by a carbon-to-carbon double bond}
- C08F 2800/20: as weight or mass percentages
- C09J 2301/312: parameters being the characterizing feature
- C09J 2433/00: Presence of (meth)acrylic polymer
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED 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)
- 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)

## Abstract

A (meth)acrylic acid copolymer (A) having a weight average molecular weight of 1000 to 1,000,000, and in which when the half-width of the primary scatter peak when measured by small angle X-ray scattering is defined as X, 0.12<X, is used as an adhesive. The (meth)acrylic copolymer (A) is obtained by polymerizing a monomer mixture containing a macromonomer (a) having a number average molecular weight of 500-100,000, and a vinyl monomer (b). The adhesive has sufficient holding force and adhesive force, and the occurrence of adhesive deposit can be prevented when peeled off.

## Claims

### Claim 1

A (meth)acrylic copolymer (A) having a weight average molecular weight of 1,000 to 1,000,000,
wherein the (meth)acrylic copolymer (A) satisfies 0.12<X, when X is defined as a half width of a primary scatter peak in small angle X-ray scattering measurement,
wherein the (meth)acrylic copolymer (A) comprises a constituent unit derived from a macromonomer (a) having a number average molecular weight of 500 to 100,000 and a constituent unit derived from a vinyl monomer (b),
wherein the macromonomer (a) is represented by Formula (1):
wherein in Formula (1):
R is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a heterocyclic group, the alkyl group, cycloalkyl group, aryl group, or heterocyclic group may have a substituent;
Z is an end group; and
the symbol “ . . . ” represents a main chain moiety comprising two or more constituent units represented by Formula (a′):
wherein in formula (a′):
P represents a hydrogen atom, a methyl group, or CH2OH:
Q is selected from the group consisting of OR, O2CR, halogen, CO2H, COR, CO2R CN, CONH2, CONHR, CONR2, and R′;
R is selected from the group consisting of a hydrogen atom, substituted and unsubstituted alkyl, substituted and unsubstituted aryl, substituted and unsubstituted heteroaryl, substituted and unsubstituted aralkyl, substituted and unsubstituted alkaryl, and substituted and unsubstituted organosilyl; the substituents are the same as or different from each other, and are selected from the group consisting of carboxylic acid, carboxylic acid ester, epoxy, hydroxyl, alkoxy, primary amino, secondary amino, tertiary amino, isocyanato, sulfonic acid, and halogen;
R′ is selected from the aromatic group consisting of substituted and unsubstituted aryl, substituted and unsubstituted heteroaryl; and the substituents are the same as or different from each other, and are selected from the group consisting of carboxylic acid, carboxylic acid ester, epoxy, hydroxyl, alkoxy, primary amino, secondary amino, tertiary amino, isocyanate, sulfonic acid, substituted and unsubstituted alkyl, substituted and unsubstituted aryl, substituted and unsubstituted olefins, and halogen.

### Claim 2 (depends on 1)

The (meth)acrylic copolymer (A) according to claim 1,
wherein the (meth)acrylic copolymer (A) has a relative dielectric constant of 3.5 or less at a frequency of 100 kHz.

### Claim 3 (depends on 1)

The (meth)acrylic copolymer (A) according to claim 1, wherein the (meth)acrylic copolymer (A) is a polymerization product of a monomer mixture comprising the macromonomer (a) having a number average molecular weight of 500 to 100,000 and the vinyl monomer (b).

### Claim 4 (depends on 1)

The (meth)acrylic copolymer (A) according to claim 1, wherein the (meth)acrylic copolymer (A) comprises a repeating unit derived from the macromonomer (a) in an amount of 7 to 40 mass %.

### Claim 5 (depends on 1)

The (meth)acrylic copolymer (A) according to claim 1, wherein the macromonomer (a) has a glass transition temperature (Tga) of 0° C. to 150° C.

### Claim 6 (depends on 1)

The (meth)acrylic copolymer (A) according to claim 1, wherein the macromonomer (a) comprises a monomer constituent unit having a (meth)acryloyl group in an amount of 80 mass % or more.

### Claim 7 (depends on 1)

An adhesive composition, comprising the (meth)acrylic copolymer (A) according to claim 1.

### Claim 8 (depends on 7)

An adhesive sheet, comprising the adhesive composition of claim 7.

### Claim 9 (depends on 1)

A coating material, comprising the (meth)acrylic copolymer (A) according to claim 1.

### Claim 10 (depends on 1)

A coated product, comprising the (meth)acrylic copolymer (A) according to claim 1.