CA2291808A1 - Pressure-sensitive adhesive composition, process for the preparation thereof and pressure-sensitive adhesive sheets - Google Patents

Pressure-sensitive adhesive composition, process for the preparation thereof and pressure-sensitive adhesive sheets Download PDF

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Publication number
CA2291808A1
CA2291808A1 CA 2291808 CA2291808A CA2291808A1 CA 2291808 A1 CA2291808 A1 CA 2291808A1 CA 2291808 CA2291808 CA 2291808 CA 2291808 A CA2291808 A CA 2291808A CA 2291808 A1 CA2291808 A1 CA 2291808A1
Authority
CA
Canada
Prior art keywords
sensitive adhesive
pressure
adhesive composition
block copolymer
epoxy
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA 2291808
Other languages
French (fr)
Other versions
CA2291808C (en
Inventor
Michiharu Yamamoto
Yutaka Moroishi
Kenichi Okada
Fumiko Kamifuji
Tomoko Doi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nitto Denko Corp
Original Assignee
Nitto Denko Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nitto Denko Corp filed Critical Nitto Denko Corp
Publication of CA2291808A1 publication Critical patent/CA2291808A1/en
Application granted granted Critical
Publication of CA2291808C publication Critical patent/CA2291808C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J153/00—Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
    • C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31511—Of epoxy ether
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31855—Of addition polymer from unsaturated monomers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31855—Of addition polymer from unsaturated monomers
    • Y10T428/31938—Polymer of monoethylenically unsaturated hydrocarbon

Abstract

A pressure-sensitive adhesive composition having well-balanced pressure-sensitive adhesive force and cohesive force without causing any safety or economy problems, a process for the preparation of the same and pressure-sensitive adhesive sheets using the same are disclosed. The pressure-sensitive adhesive composition comprises a crosslinked polymer obtained by crosslinking a block copolymer comprising at least two of a styrene-based polymer block A and an acrylic polymer block B having a structural unit represented by the general formula (1): -[CH2-C(R1)COOR2]- wherein R1 represents a hydrogen atom or methyl group, and R2 represents a C2-14 alkyl group, bonded each other, such as A-B or B-A type block copolymer and A-B-A
type block copolymer.

Claims (20)

1. A pressure-sensitive adhesive composition comprising a crosslinked polymer obtained by crosslinking a block copolymer comprising at least two of a styrene-based polymer block A and an acrylic polymer block B having a structural unit represented by the general formula (1):
-[CH2-C(R1)COOR2]- wherein R1 represents a hydrogen atom or methyl group, and R2 represents a C2-14 alkyl group, bonded each other.
2. The pressure-sensitive adhesive composition as claimed in claim 1, wherein said block copolymer is an A-B type or B-A type block copolymer.
3. The pressure-sensitive adhesive composition as claimed in claim 2, wherein said styrene-based polymer block A is present in an amount not exceeding 50% by weight based on the total weight of said block copolymer.
4. The pressure-sensitive adhesive composition as claimed in claim 1, wherein said block copolymer is an A-B-A type block copolymer.
5. The pressure-sensitive adhesive composition as claimed in claim 9, wherein said styrene-based polymer block A is present in an amount not exceeding 60% by weight based on the total weight of said block copolymer.
6. The pressure-sensitive adhesive composition as claimed in claim 1, 2, 3, 4 or 5, wherein said block copolymer contains a hydroxyl group in its polymer chain and is heat-crosslinked with addition of a polyfunctional isocyanate thereto.
7. The pressure-sensitive adhesive composition as claimed in claim 1, 2, 3, 4 or 5, wherein said block copolymer contains an epoxy group in its polymer chain and is irradiated with ultraviolet rays with addition of an opium salt-based curing catalyst thereto to epoxy-crosslink.
8. The pressure-sensitive adhesive composition as claimed in claim 7, wherein said block copolymer contains at least two epoxy groups per molecule.
9. The pressure-sensitive adhesive composition as claimed in claim 8, wherein said epoxy groups are incorporated in said block copolymer at or in the vicinity of the end of molecular chain thereof.
10. The pressure-sensitive adhesive composition as claimed in claim 7, wherein said block copolymer contains at least one epoxy group and at least one hydroxyl group per molecule.
11. The pressure-sensitive adhesive composition as claimed in claim 10, wherein said epoxy groups are incorporated in said block copolymer at or in the vicinity of the end of molecular chain thereof and said hydroxyl groups are incorporated in said block copolymer at or in the vicinity of molecular chain thereof.
12. The pressure-sensitive adhesive composition as claimed in claim 7, wherein said block copolymer contains at least two hydroxyl groups per molecule and is epoxy-crosslinked with addition of the opium salt-based curing catalyst and an epoxy-based crosslinking agent thereto.
13. The pressure-sensitive adhesive composition as claimed in claim 12, wherein said hydroxyl groups are incorporated in said block copolymer at or in the vicinity of the end of molecular chain thereof.
14. A process for the preparation of a pressure-sensitive adhesive composition, which comprises subjecting a styrene-based monomer and an acrylic monomer represented by the general formula (1A): CH2-C(R1)COOR1 wherein R1 represents a hydrogen atom or methyl group, and R2 represents a C2-14 alkyl group, to a living radical polymerization in an appropriate order of monomers using a polymerization initiator in the presence of a transition metal and its ligand to produce a block copolymer comprising at least two of a styrene-based polymer block A and an acrylic polymer block B bonded each other, and then subjecting said block copolymer to crosslinking to produce a crosslinked polymer.
15. The process for the preparation of a pressure-sensitive adhesive composition as claimed in claim 14, wherein said transition metal is Cu, Ru, Fe, Rh, V or Ni and its ligand is a bipyridine derivative,mercaptan derivative or trifluorate derivative.
16. The process for the preparation of a pressure-sensitive adhesive composition as claimed in claim 15, wherein a combination of said transition metal and said ligand is Cu+1-bipyridine complex.
17. The process for the preparation of a pressure-sensitive adhesive composition as claimed in claim 14, wherein said polymerization initiator is an ester- or styrene-based derivative containing a halogen in .alpha.-position.
18. The process for the preparation of an pressure-sensitive adhesive composition as claimed in claim 14, wherein said polymerization initiator contains an epoxy group or hydroxyl group in its molecule.
19. The process for the preparation of an pressure-sensitive adhesive composition as claimed in claim 14, wherein said styrene-based monomer and said acrylic monomer are subjected to a living radical polymerization together with at least one monomer selected from the group consisting of a monomer having an epoxy group in its molecule and a monomer having a hydroxyl group in its molecule.
20. Pressure-sensitive adhesive sheets comprising a support and a layer of the pressure-sensitive adhesive composition as claimed in claim 1 provided thereon.
CA 2291808 1998-12-08 1999-12-07 Pressure-sensitive adhesive composition, process for the preparation thereof and pressure-sensitive adhesive sheets Expired - Fee Related CA2291808C (en)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
JP10-348335 1998-12-08
JP34833598 1998-12-08
JP17022099 1999-06-16
JP11-170220 1999-06-16
JP11-223149 1999-08-06
JP22314999 1999-08-06
JP30823099A JP4572006B2 (en) 1998-12-08 1999-10-29 Adhesive composition, method for producing the same, and adhesive sheet
JP11-308230 1999-10-29

Publications (2)

Publication Number Publication Date
CA2291808A1 true CA2291808A1 (en) 2000-06-08
CA2291808C CA2291808C (en) 2010-04-13

Family

ID=27474314

Family Applications (1)

Application Number Title Priority Date Filing Date
CA 2291808 Expired - Fee Related CA2291808C (en) 1998-12-08 1999-12-07 Pressure-sensitive adhesive composition, process for the preparation thereof and pressure-sensitive adhesive sheets

Country Status (5)

Country Link
US (1) US6432475B1 (en)
EP (1) EP1008640B1 (en)
JP (1) JP4572006B2 (en)
CA (1) CA2291808C (en)
DE (1) DE69918930T2 (en)

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* Cited by examiner, † Cited by third party
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US7999052B2 (en) 2006-09-07 2011-08-16 Tokyo Ohka Kogyo Co., Ltd. Process for producing an adhesive composition

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Also Published As

Publication number Publication date
JP2001115124A (en) 2001-04-24
JP4572006B2 (en) 2010-10-27
DE69918930D1 (en) 2004-09-02
US6432475B1 (en) 2002-08-13
CA2291808C (en) 2010-04-13
EP1008640B1 (en) 2004-07-28
DE69918930T2 (en) 2004-12-16
EP1008640A1 (en) 2000-06-14

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