IP Library Granted Patent US 9,163,166
Granted Patent B2
US 9,163,166 · App. 12/801,109 · Granted Oct 20, 2015

Adhesive composition, optical member, and surface protective sheet

Inventors: Cheong Hun Song (Uiwang-si, KR); Tatsuhiro Suwa (Kanagawa, JP); Hiroshi Ogawa (Kanagawa, JP)
Assignee: CHEIL INDUSTRIES, INC.
C09J11/06C08K5/3432C08K5/3435C08K5/49C09J133/08C09J133/26G02B1/16G02B5/305Y10T428/2887
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Quick Facts
Patent No.
US 9,163,166
App. No.
12/801,109
Filed
May 24, 2010
Granted
Oct 20, 2015
Kind
B2
Examiner
SHAH, SAMIR
Art Unit
1787
USPC
428/355CN
Abstract

An adhesive composition includes a copolymer (A), the copolymer (A) being a copolymer of: a hydroxyl group-containing (meth)acrylamide (a1), the hydroxyl group-containing (meth)acrylamide (a1) including at least one of a hydroxyl group-containing acrylamide and a hydroxyl group-containing methacrylamide, and a (meth)acrylate (a2), the (meth)acrylate (a2) including at least one of an acrylic ester and a methacrylic ester; and an antistatic agent (B), the antistatic agent (B) including an ionic compound.

Claims (45)

1. An adhesive composition for forming a peelable adhesive layer, the composition comprising:

a copolymer (A), the copolymer (A) being a copolymer of:

a hydroxyl group-containing (meth)acrylamide (a1), the hydroxyl group-containing (meth)acrylamide (a1) including at least one of a hydroxyl group-containing acrylamide and a hydroxyl group-containing methacrylamide, the hydroxyl group-containing (meth)acrylamide (a1) being represented by the following formula: H 2 C═C(R1)ACONHCH 2 CH 2 OH, in which:

R1 is H or CH 3 ,

A is a linking group, the linking group being (COOCH 2 CH 2 ) n , COOCH 2 CH 2 OOC—CH 2 CH 2 , or Compound 1 represented by Chemical Formula 1:

 and

n is 1 or 2, and

a (meth)acrylate (a2), the (meth)acrylate (a2) including at least one of an acrylic ester and a methacrylic ester, the (meth)acrylate (a2) including at least one of methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, t-butyl (meth)acrylate, isobutyl (meth)acrylate, hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, n-octyl (meth)acrylate, isooctyl (meth)acrylate, n-nonyl (meth)acrylate, isononyl (meth)acrylate, n-decyl (meth)acrylate, isodecyl (meth)acrylate, n-dodecyl (meth)acrylate, n-tridecyl (meth)acrylate, n-tetradecyl (meth)acrylate, methoxyethyl (meth)acrylate, ethoxyethyl (meth)acrylate, butoxyethyl (meth)acrylate, cyclohexyl (meth)acrylate, t-butylcyclohexyl (meth)acrylate, phenoxyethyl (meth)acrylate, nonylphenoxy polyethylene glycol (meth)acrylate, benzyl (meth)acrylate, isobornyl (meth)acrylate, n-butyl acrylate, and tetrahydrofurfuryl (meth)acrylate,

wherein the copolymer (A) includes about 0.1 to about 10% by weight of the hydroxyl group-containing (meth)acrylamide (a1) and about 50 to about 99.1% by weight of the (meth)acrylate (a2) based on a total weight of the copolymer (A); and

an antistatic agent (B), the adhesive composition including about 0.01 to about 2.0% by weight of the antistatic agent (B), and the antistatic agent (B) including an ionic compound, wherein:

the copolymer (A) is crosslinked,

the copolymer (A) has a polystyrene conversion weight-average molecular weight of about 300,000 to about 1,000,000 as determined by gel permeation chromatography,

the composition has a gel fraction, at 3 days at 23° C. under a relative humidity of 50%, of about 90 to about 100% as a crosslinking degree,

the composition has an adhesive force of about 0.05 (N/25 mm) to about 0.2 (N/25 mm) measured according to JIS Z0237,

the ionic compound is at least one selected from a pyridinium salt, an alkyl pyrrolidium salt, and N-methyl-N-propylpiperidinium bis(trifluoromethanesulfonyl)imide, and

the composition provides an adhesive layer that has a sheet resistance of about 1×10 8 to about 1×10 11 Ω/cm 2 .

2. The adhesive composition as claimed in claim 1 , wherein:

the adhesive composition is for a surface protection sheet.

3. The adhesive composition as claimed in claim 1 , wherein:

the adhesive composition is for a surface protective sheet, and

the copolymer (A) includes about 50 to about 99.1% by weight of 2-ethylhexylacrylate as the (meth)acrylate (a2) based on a total weight of the copolymer (A).

4. The adhesive composition as claimed in claim 1 , wherein:

the adhesive composition is for an optical member.

5. The adhesive composition as claimed in claim 1 , wherein the copolymer (A) has a glass transition temperature (Tg) of about 0° C. or less.

6. A surface protection sheet, comprising:

a protective film; and

an adhesive layer formed on one or both sides of the protective film, the adhesive layer including the adhesive composition according to claim 1 .

7. An adhesive composition for an optical member, the composition comprising:

a copolymer (A), the copolymer (A) being a copolymer of:

a hydroxyl group-containing (meth)acrylamide (a1), the hydroxyl group-containing (meth)acrylamide (a1) including at least one of a hydroxyl group-containing acrylamide and a hydroxyl group-containing methacrylamide, the hydroxyl group-containing (meth)acrylamide (a1) being represented by the following formula: H 2 C═C(R1)ACONHCH 2 CH 2 OH, in which:

R1 is H or CH 3 ,

A is a linking group, the linking group being (COOCH 2 CH 2 ) n , COOCH 2 CH 2 OOC—CH 2 CH 2 , or Compound 1 represented by Chemical Formula 1:

 and

n is 1 or 2, and

a (meth)acrylate (a2), the (meth)acrylate (a2) including at least one of an acrylic ester and a methacrylic ester, the (meth)acrylate (a2) including at least one of methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, t-butyl (meth)acrylate, isobutyl (meth)acrylate, hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, n-octyl (meth)acrylate, isooctyl (meth)acrylate, n-nonyl (meth)acrylate, isononyl (meth)acrylate, n-decyl (meth)acrylate, isodecyl (meth)acrylate, n-dodecyl (meth)acrylate, n-tridecyl (meth)acrylate, n-tetradecyl (meth)acrylate, methoxyethyl (meth)acrylate, ethoxyethyl (meth)acrylate, butoxyethyl (meth)acrylate, cyclohexyl (meth)acrylate, t-butylcyclohexyl (meth)acrylate, phenoxyethyl (meth)acrylate, nonylphenoxy polyethylene glycol (meth)acrylate, benzyl (meth)acrylate, isobornyl (meth)acrylate, n-butyl acrylate, and tetrahydrofurfuryl (meth)acrylate;

wherein the copolymer (A) includes about 0.1 to about 10% by weight of the hydroxyl group-containing (meth)acrylamide (a1) and about 50 to about 99.1% by weight of the (meth)acrylate (a2) based on a total weight of the copolymer (A), and

an antistatic agent (B), the adhesive composition including about 0.01 to about 2.0% by weight of the antistatic agent (B), and the antistatic agent (B) including an ionic compound, wherein:

the ionic compound is at least one selected from a pyridinium salt, an alkyl pyrrolidium salt, and N-methyl-N-propylpiperidinium bis(trifluoromethanesulfonyl)imide,

the copolymer (A) is crosslinked,

the copolymer (A) has a polystyrene conversion weight-average molecular weight of about 1,000,000 to about 2,000,000 as determined by gel permeation chromatography,

the composition has a gel fraction, at 3 days at 23° C. under a relative humidity of 50%, of about 50 to about 80% as a crosslinking degree, and

the composition provides an adhesive layer that has a sheet resistance of about 1×10 8 to about 1×10 11 Ω/cm 2 .

8. A surface protection sheet, comprising:

a protective film optical sheet; and

an adhesive layer formed on one or both sides of the optical sheet, the adhesive layer including the adhesive composition according to claim 7 .

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 4, 2026
From: WUXI HENGXIN OPTOELECTRONIC MATERIALS CO., LTD.
To: HOARDSUN HENGXIN(WUXI) MATERIALS CO., LTD.
Reel/Frame 075049/0450 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 14, 2025
From: SAMSUNG SDI CO., LTD.
To: WUXI HENGXIN OPTOELECTRONIC MATERIALS CO., LTD.
Reel/Frame 073062/0496 →
MERGER Recorded Jun 16, 2025
From: CHEIL INDUSTRIES INC.
To: SAMSUNG SDI CO., LTD.
Reel/Frame 071636/0099 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 24, 2010
From: SONG, CHEONG HUN; SUWA, TATSUHIRO; OGAWA, HIROSHI
To: CHEIL INDUSTRIES, INC.
Reel/Frame 024490/0687 →
Priority Claims (1)
JP 2007-302702 · Nov 22, 2007 · national
Continuity (2)
Continuation PCTKR2008006501 · Nov 4, 2008
Related Publication 20100239859A1 · Sep 23, 2010