WO2018016407A1 - Copolymère séquencé, composition, et film - Google Patents

Copolymère séquencé, composition, et film Download PDF

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Publication number
WO2018016407A1
WO2018016407A1 PCT/JP2017/025494 JP2017025494W WO2018016407A1 WO 2018016407 A1 WO2018016407 A1 WO 2018016407A1 JP 2017025494 W JP2017025494 W JP 2017025494W WO 2018016407 A1 WO2018016407 A1 WO 2018016407A1
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WO
WIPO (PCT)
Prior art keywords
block
group
meth
block copolymer
acrylate
Prior art date
Application number
PCT/JP2017/025494
Other languages
English (en)
Japanese (ja)
Inventor
石飛宏幸
Original Assignee
大塚化学株式会社
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 大塚化学株式会社 filed Critical 大塚化学株式会社
Priority to KR1020187035031A priority Critical patent/KR102112439B1/ko
Priority to CN201780042669.9A priority patent/CN109476797B/zh
Priority to JP2018528513A priority patent/JP6728356B2/ja
Publication of WO2018016407A1 publication Critical patent/WO2018016407A1/fr

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
    • B32B27/308—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers comprising acrylic (co)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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K7/00—Use of ingredients characterised by shape
    • C08K7/02—Fibres or whiskers
    • C08K7/04—Fibres or whiskers inorganic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • 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
    • C09D153/00—Coating compositions based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/002—Priming paints
    • 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

Definitions

  • Polypropylene resin hereinafter also referred to as “PP”
  • PE polyethylene resin
  • PP and PE are inexpensive and versatile resins having excellent moldability, chemical resistance, water resistance, electrical properties, and the like. It is. PP and PE are widely used in applications such as automobiles, home appliances, agriculture, and printing.
  • Cycloolefin resins hereinafter also referred to as “COP”) have excellent characteristics such as high transparency, low hygroscopicity, and low specific gravity. This COP is used for optical members such as displays and touch panels as an alternative material for glass and transparent plastics.
  • polyolefin resins such as PP, PE, and COP have low polarity and few functional groups present on the surface of the member, so that coating, adhesion, and the like are difficult.
  • (Meth) acrylic monomers include (meth) acrylic acid, (meth) acrylic acid aliphatic alkyl (straight chain alkyl, branched chain alkyl) ester, (meth) acrylic acid alicyclic alkyl (monocyclic structure) ester, hydroxy Group (meth) acrylate, alkoxy group (meth) acrylate, sulfonic acid group (meth) acrylate, tertiary amine-containing (meth) acrylate, epoxy group-containing (meth) acrylate, polyethylene glycol Examples include (meth) acrylate having a structural unit, (meth) acrylate having an aromatic ring group, and (meth) acrylamide.
  • Examples of the (meth) acrylate having an alkoxy group include methoxyethyl (meth) acrylate and ethoxyethyl (meth) acrylate.
  • Examples of the (meth) acrylate having a sulfonic acid group include ethyl disulfonate (meth) acrylate.
  • Examples of the tertiary amine-containing unsaturated monomer include 2- (dimethylamino) ethyl (meth) acrylate and N, N-dimethylaminopropyl (meth) acrylate.
  • Examples of the (meth) acrylate containing an epoxy group include glycidyl (meth) acrylate.
  • Examples of the (meth) acrylate having an aromatic ring group include benzyl (meth) acrylate, phenyl (meth) acrylate, and phenoxyethyl (meth) acrylate.
  • Examples of (meth) acrylamide include (meth) acrylamide, N-methyl (meth) acrylamide, N-isopropyl (meth) acrylamide, N, N-dimethyl (meth) acrylamide and the like.
  • the content of the structural unit derived from the (meth) acrylate having an aliphatic alkyl group is 15% by mass in 100% by mass of the A block.
  • the above is preferable, More preferably, it is 20 mass% or more, More preferably, it is 25 mass% or more. If the content of the structural unit derived from the (meth) acrylate having an aliphatic alkyl group in the A block is within the above range, when used in the adhesive composition or the pressure-sensitive adhesive composition, The adhesion of is further improved.
  • the vinyl monomer used for the B block is preferably a vinyl monomer containing a heterocycle or a (meth) acryl monomer, more preferably a vinyl monomer containing a heterocycle, an aliphatic alkyl (meth) acrylate (linear alkyl, (Branched alkyl) ester, (meth) acrylate having a hydroxy group, (meth) acrylate having an alkoxy group, more preferably a vinyl monomer containing a heterocycle, an aliphatic alkyl (preferably having 1 to 18 carbon atoms, more preferably It is a (meth) acrylate having a group having 1 to 10 carbon atoms.
  • the phase separation structure forms a lamellar structure, a gyro structure, a cylinder structure, or a sea-island structure depending on the mass ratio, volume ratio, polymerization degree, and the like of each block in the block copolymer.
  • the phase separation structure is not particularly limited.
  • a second B block bonded together.
  • the first A block and the second A block are preferably present at the ends of the block copolymer.
  • the first B block and the second B block are preferably present at the ends of the block copolymer, respectively.
  • the content of the A block in the block copolymer is preferably 40% by mass or more, more preferably 50% by mass or more, and still more preferably 60% by mass or more in 100% by mass of the entire block copolymer. It is preferably at most mass%, more preferably at most 85 mass%, further preferably at most 75 mass%.
  • the content of each block is determined from the charge ratio of monomers constituting the block copolymer and the polymerization rate of each monomer.
  • the TERP method is a method of polymerizing a radical polymerizable compound (vinyl monomer) using an organic tellurium compound as a polymerization initiator.
  • a radical polymerizable compound vinyl monomer
  • organic tellurium compound organic tellurium compound
  • the growth terminal of the copolymer obtained by the polymerization reaction is in the form of -TeR 1 derived from a tellurium compound (wherein R 1 is the same as described above), and is deactivated by manipulation in air after completion of the polymerization reaction.
  • R 1 is the same as described above
  • tellurium atoms may remain. Since the copolymer in which the tellurium atom remains at the terminal is colored or inferior in thermal stability, it is preferable to remove the tellurium atom.
  • Aromatic diisocyanates such as 4,4'-diphenylmethane diisocyanate, xylylene diisocyanate, polymethylene polyphenyl isocyanate; trimethylolpropane / tolylene diisocyanate trimer adduct, trimethylolpropane / hexamethylene diisocyanate trimer adduct , Isocyanate adducts such as isocyanurate of hexamethylene diisocyanate; xylylene diisocyanate Trimethylolpropane adduct of hexamethylene diisocyanate; Trimethylolpropane adduct of hexamethylene diisocyanate; Polyether polyisocyanate, polyester polyisocyanate, and adducts of these with various polyols, isocyanurate bond, burette bond, allophanate bond, etc. Polyfunctionalized polyisocyanate; and the like.
  • Examples of the layer formed from the composition include a primer layer, a surface modification layer (for example, a hard coat layer), an adhesive layer, and a pressure-sensitive adhesive layer.
  • the surface modification layer (for example, hard coat layer) can be formed by applying the hard coat composition onto a substrate, drying it, and curing the hard coat agent.
  • the coating method of the said composition for hard-coats is not specifically limited, The method similar to the said primer composition is employable. What is necessary is just to select the method of hardening a hard-coat agent suitably according to a hard-coat agent.
  • the adhesion of the hard coat layer to the substrate was evaluated by a cross-cut tape method (former JIS K5400 (1990) standard, cut interval 1 mm), and the results are shown in Table 10. Further, the hardness of the hard coat surface layer was evaluated by a steel wool resistance test. Steel wool resistance was evaluated by rounding the steel wool count # 0000, reciprocating it manually several times, and rubbing it. The results are shown in Table 10.
  • a pressure-sensitive adhesive composition was prepared by mixing 11 parts by mass of 11 or 12, 9 parts by mass of a solvent (tetrahydrofuran), and a crosslinking agent.
  • a crosslinking agent tetrahydrofuran
  • crosslinking agent 1 manufactured by Mitsubishi Gas Chemical Company, TETRAD-X
  • crosslinking agent 2 manufactured by Asahi Kasei Corporation, Duranate (registered trademark) TPA-100
  • the amount of the crosslinking agent was 0.021 parts by mass in the case of crosslinking agent 1 (TETRAD-X) and 0.0066 parts by mass in the case of crosslinking agent 2 (D-TPA).
  • Aspect 6 The block copolymer according to any one of embodiments 1 to 5, wherein the block copolymer is polymerized by living radical polymerization.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Manufacturing & Machinery (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Graft Or Block Polymers (AREA)
  • Paints Or Removers (AREA)
  • Inorganic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Epoxy Resins (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Laminated Bodies (AREA)
  • Adhesive Tapes (AREA)

Abstract

L'invention fournit un copolymère séquencé qui non seulement consiste en un matériau de polarité élevée, mais en plus possède une forte adhérence (adésion) vis-à-vis d'un matériau de faible polarité, sans mettre en œuvre de composé contenant un chlore. Ce copolymère séquencé est caractéristique en ce qu'il possède une séquence A qui possède une unité structurale dérivée d'un monomère de vinyle possédant un groupe hydrocarbure aliphatique polycyclique, et une séquence B qui possède une unité structurale dérivée d'un monomère de vinyle. La température moyenne de transition vitreuse de ladite séquence A est supérieure ou égale à 25°C, la température moyenne de transition vitreuse de ladite séquence B est plus basse que celle de ladite séquence A, et la différence entre les températures moyennes de transition vitreuse desdites séquences A et B est supérieure ou égale à 50°C.
PCT/JP2017/025494 2016-07-21 2017-07-13 Copolymère séquencé, composition, et film WO2018016407A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
KR1020187035031A KR102112439B1 (ko) 2016-07-21 2017-07-13 블록 공중합체, 조성물 및 필름
CN201780042669.9A CN109476797B (zh) 2016-07-21 2017-07-13 嵌段共聚物、组合物和膜
JP2018528513A JP6728356B2 (ja) 2016-07-21 2017-07-13 ブロック共重合体、組成物およびフィルム

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2016143721 2016-07-21
JP2016-143721 2016-07-21

Publications (1)

Publication Number Publication Date
WO2018016407A1 true WO2018016407A1 (fr) 2018-01-25

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Country Status (5)

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JP (2) JP6728356B2 (fr)
KR (1) KR102112439B1 (fr)
CN (1) CN109476797B (fr)
TW (2) TWI750892B (fr)
WO (1) WO2018016407A1 (fr)

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JP2019104857A (ja) * 2017-12-13 2019-06-27 東亞合成株式会社 ブロック共重合体の製造方法
WO2020149387A1 (fr) * 2019-01-16 2020-07-23 積水フーラー株式会社 Copolymere sequence reticulable, son procede de fabrication ainsi qu'element elastique
WO2020149388A1 (fr) * 2019-01-16 2020-07-23 積水フーラー株式会社 Copolymere sequence reticulable et adhesif thermofusible
WO2020149385A1 (fr) * 2019-01-16 2020-07-23 積水フーラー株式会社 Copolymère séquencé réticulable et agent de revêtement
JP2020180214A (ja) * 2019-04-25 2020-11-05 大塚化学株式会社 Ｎ−アルケニルラクタム系ブロック共重合体を含有する重合生成物および重合生成物の製造方法
JP2020180215A (ja) * 2019-04-25 2020-11-05 大塚化学株式会社 表面改質剤組成物
JP2021070765A (ja) * 2019-10-31 2021-05-06 日東電工株式会社 光学用粘着剤組成物
CN113337246A (zh) * 2021-06-01 2021-09-03 深圳市东升塑胶制品有限公司 一种用于难附着基材的光固化热熔胶及其制备方法
WO2021200730A1 (fr) * 2020-03-31 2021-10-07 日東電工株式会社 Composition adhésive sensible à la pression optique et objet multicouche optique
EP4169994A1 (fr) 2021-10-25 2023-04-26 Nitto Belgium NV Composition adhésive sensible à la pression et feuilles de protection de surface la comprenant
CN116218268A (zh) * 2023-02-28 2023-06-06 广东希贵光固化材料有限公司 一种uv固化pp底漆

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JP6888181B1 (ja) * 2019-12-06 2021-06-16 大塚化学株式会社 粘着材、粘着シートおよび屈曲性積層部材
JP6814317B1 (ja) * 2019-12-13 2021-01-13 東洋インキＳｃホールディングス株式会社 ブロック共重合体、樹脂組成物、伸縮性導体、電子デバイスおよび粘着フィルム
JP7526020B2 (ja) * 2020-03-31 2024-07-31 日東電工株式会社 光学積層体
JP7478574B2 (ja) * 2020-03-31 2024-05-07 日東電工株式会社 光学積層体
CN114437654B (zh) * 2021-12-24 2023-06-13 英创新材料(绍兴)有限公司 一种水性快凝型胶粘剂及其制备方法

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Publication number Priority date Publication date Assignee Title
JP7081134B2 (ja) 2017-12-13 2022-06-07 東亞合成株式会社 ブロック共重合体の製造方法
JP2019104857A (ja) * 2017-12-13 2019-06-27 東亞合成株式会社 ブロック共重合体の製造方法
JPWO2020149385A1 (ja) * 2019-01-16 2021-02-18 積水フーラー株式会社 架橋性ブロック共重合体及びコーティング剤
WO2020149387A1 (fr) * 2019-01-16 2020-07-23 積水フーラー株式会社 Copolymere sequence reticulable, son procede de fabrication ainsi qu'element elastique
WO2020149388A1 (fr) * 2019-01-16 2020-07-23 積水フーラー株式会社 Copolymere sequence reticulable et adhesif thermofusible
WO2020149385A1 (fr) * 2019-01-16 2020-07-23 積水フーラー株式会社 Copolymère séquencé réticulable et agent de revêtement
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CN109476797A (zh) 2019-03-15
TWI750892B (zh) 2021-12-21
TW201815857A (zh) 2018-05-01
TW202115142A (zh) 2021-04-16
JP6728356B2 (ja) 2020-07-22
JP6945692B2 (ja) 2021-10-06
JP2020169336A (ja) 2020-10-15
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