# US 7,744,998 B2 · Plasticizer-resistant pressure-sensitive adhesive composition and adhesive article

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- Number: US 7,744,998 B2
- Document ID: US7744998B2
- Status: Granted
- Kind: B2
- Application number: 10/473,917
- Filed: 2002-04-22
- Published: 2004-07-22
- Granted: 2010-06-29
- Earliest claimed: 2001-04-25
- Assignees: 3M Innovative Properties Company
- Inventors: Shojitsu Nakamuta
- Web page: https://patentgrep.com/patent/US7744998B2

## CPC

- C09J 133/26: Homopolymers or copolymers of acrylamide or methacrylamide
- C08F 220/1807: {C7-(meth)acrylate, e.g. heptyl (meth)acrylate or benzyl (meth)acrylate}
- C08F 220/1808: {C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate}
- C09J 133/04: Homopolymers or copolymers of esters {(C09J143/04 takes precedence)}
- C09J 133/14: of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
- C09J 2301/302: the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C
- Y10T 428/249983: As outermost component
- Y10T 428/249985: Composition of adhesive or bonding component specified
- Y10T 428/2887: including nitrogen containing polymer [e.g., polyacrylonitrile, polymethacrylonitrile, etc.]
- Y10T 428/2891: including addition polymer from alpha-beta unsaturated carboxylic acid [e.g., acrylic acid, methacrylic acid, etc.] Or derivative thereof
- 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)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

There is provided a pressure-sensitive adhesive composition which has a high initial adhesive strength to an adherend containing a plasticizer and can maintain the adhesive strength even after long-term use. A plasticizer-resistant pressure-sensitive adhesive composition comprising a copolymer obtained by polymerizing a monomer mixture comprising (a) an aromatic-containing (meth)acrylate monomer, (b) a nitrogen-containing vinyl monomer, and (c) an alkyl(meth)acrylate monomer, an alkyl group of which has 4 to 14 carbon atoms.

## Claims

### Claim 1

A pressure-sensitive adhesive article comprising:
a) an adherend having a plasticizer; and
b) a plasticizer-resistant pressure-sensitive adhesive composition comprising a copolymer comprising the reaction product of a monomer mixture comprising:
i. 5 to 30% by weight of an aromatic-containing (meth)acrylate;
ii. 30 to 70% by weight of a nitrogen-containing vinyl monomer; and
iii. 20 to 50% by weight of an alkyl(meth)acrylate comprising an alkyl group having from 4 to 14 carbon atoms.

### Claim 2 (depends on 1)

The pressure-sensitive adhesive article of claim 1, wherein the monomer mixture further comprises a crosslinking agent.

### Claim 3 (depends on 1)

The pressure-sensitive adhesive article of claim 1, wherein the aromatic-containing (meth)acrylate is phenyl(meth)acrylate, benzyl(meth)acrylate, phenoxyethyl(meth)acrylate, phenoxypropyl(meth)acrylate, phenoxydiethylene glycol (meth)acrylate, or phenoxyhydroxypropyl(meth)acrylate.

### Claim 4 (depends on 1)

The pressure-sensitive adhesive article of claim 1, wherein the aromatic-containing (meth)acrylate is benzyl(meth)acrylate, phenyl(meth)acrylate, or phenoxyethyl(meth)acrylate.

### Claim 5 (depends on 1)

The pressure-sensitive adhesive article of claim 1, wherein the nitrogen-containing vinyl monomer is N,N-dimethylacrylamide, N,N-dimethylmethacrylamide, N,N-diethylacrylamide, N,N-diethylmethacrylamide, N,N-dimethylaminoethyl methacrylate, N,N-dimethylaminoethyl acrylate, N,N-dimethylaminopropyl methacrylate, N,N-dimethylaminopropyl acrylate, N-hexylacrylamide, β-(dimethylamide)ethyl acrylate, N-methylacrylamide, N-ethylacrylamide, N-vinylpyrrolidone, N-vinyl caprolactone, or N,N-pentaethyleneacrylamide.

### Claim 6 (depends on 1)

The pressure-sensitive adhesive article of claim 1, wherein the nitrogen-containing vinyl monomer is N,N-dimethylacrylamide, N,N-dimethylacrylamide, N,N-dimethylmethacrylamide, or N,N-diethylacrylamide.

### Claim 7 (depends on 1)

The pressure-sensitive adhesive article of claim 1, wherein the alkyl (meth)acrylate monomer is N-butyl(meth)acrylate, isobutyl(meth)acrylate, 2-methylbutyl (meth)acrylate, 2-ethylhexyl(meth)acrylate, n-octyl(meth)acrylate, isooctyl(meth)acrylate, isononyl(meth)acrylate, or isodecyl(meth)acrylate.

### Claim 8 (depends on 1)

The pressure-sensitive adhesive article of claim 1, wherein the alkyl (meth)acrylate monomer is 2-ethylhexyl(meth)acrylate, isooctyl(meth)acrylate, or n-octyl (meth)acrylate.

### Claim 9 (depends on 1)

The pressure-sensitive adhesive article of claim 1, wherein the monomer mixture is free of acrylic acid and methacrylic acid.

### Claim 10 (depends on 1)

The pressure-sensitive adhesive article of claim 1, further comprising a substrate, wherein the pressure-sensitive adhesive is between the substrate and the adherend, said substrate being an acrylic foam, polyester film treated with silicone, or polyethylene film.

### Claim 11 (depends on 1)

The pressure-sensitive adhesive article of claim 1, further comprising a substrate, wherein the pressure-sensitive adhesive is between the substrate and the adherend, said substrate being an acrylic foam.

### Claim 12 (depends on 1)

The pressure-sensitive adhesive article of claim 1, wherein the adherend comprises a polyvinyl chloride.

### Claim 13 (depends on 1)

The pressure-sensitive adhesive article of claim 1, wherein the adherend comprises an elastomer.

### Claim 14 (depends on 13)

The pressure-sensitive adhesive article of claim 13, wherein the elastomer is an ethylene-propylene-diene terpolymer.

### Claim 15 (depends on 1)

The pressure-sensitive adhesive article of claim 1, wherein the adherend is an emblem, body side molding, or weather strip.

### Claim 16 (depends on 1)

The pressure-sensitive adhesive article of claim 1, wherein said plasticizer-resistant pressure-sensitive adhesive composition exhibits an initial adhesive strength to a polyvinyl chloride sheet, after pressing with a 2 kg rubber roll, as measured by a 180° peel test at 20° C. of at least 14.10 N/12 mm, and an aged adhesive strength to a polyvinyl chloride sheet, after pressing with a 2 kg rubber roll and being subjected to an oven temperature of 70° C. for a week, as measured by a 180° peel test at 20° C. of at least 13.25 N/12 mm.