JP6848983B2 - 粘着剤組成物及びその利用 - Google Patents
粘着剤組成物及びその利用 Download PDFInfo
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- JP6848983B2 JP6848983B2 JP2018555051A JP2018555051A JP6848983B2 JP 6848983 B2 JP6848983 B2 JP 6848983B2 JP 2018555051 A JP2018555051 A JP 2018555051A JP 2018555051 A JP2018555051 A JP 2018555051A JP 6848983 B2 JP6848983 B2 JP 6848983B2
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- 125000005498 phthalate group Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000010734 process oil Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012783 reinforcing fiber Substances 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003329 sebacic acid derivatives Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- GEKDEMKPCKTKEC-UHFFFAOYSA-N tetradecane-1-thiol Chemical compound CCCCCCCCCCCCCCS GEKDEMKPCKTKEC-UHFFFAOYSA-N 0.000 description 1
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 229940103494 thiosalicylic acid Drugs 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- WRSPWQHUHVRNFV-UHFFFAOYSA-N tris[3,5-di(nonyl)phenyl] phosphite Chemical compound CCCCCCCCCC1=CC(CCCCCCCCC)=CC(OP(OC=2C=C(CCCCCCCCC)C=C(CCCCCCCCC)C=2)OC=2C=C(CCCCCCCCC)C=C(CCCCCCCCC)C=2)=C1 WRSPWQHUHVRNFV-UHFFFAOYSA-N 0.000 description 1
- 239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
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- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
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- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/281—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
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- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/08—Homopolymers or copolymers of acrylic acid esters
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- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/10—Homopolymers or copolymers of methacrylic acid esters
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- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/10—Homopolymers or copolymers of methacrylic acid esters
- C09J133/12—Homopolymers or copolymers of methyl methacrylate
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- C09J157/00—Adhesives based on unspecified polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
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- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
- C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C09J7/385—Acrylic polymers
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/302—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/312—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier parameters being the characterizing feature
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- C09J2433/00—Presence of (meth)acrylic polymer
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- C09J2467/00—Presence of polyester
- C09J2467/006—Presence of polyester in the substrate
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Adhesive Tapes (AREA)
Description
また、例えばディスプレイに粘着シート加工を施す場合には、ハンドリングのよさやリワーク性の観点から、低タックでありながら加熱又は加圧により強固に接着するような特性を有する粘着剤が求められる場合もある。
前記ビニル重合体(A)は、ガラス転移温度(Tg)が60℃以上200℃以下であり、数平均分子量が500以上10,000以下であって、前記アクリル系粘着性ポリマー(B)100質量部に対して0.5質量部以上60質量部以下含有し、
前記粘着剤組成物をセパレーターに塗工し、乾燥させて粘着剤層を得た際に、当該粘着剤層全体のガラス転移温度である第1のTgが−80℃以上10℃以下であり、
前記粘着剤層のX線光電子分光分析により得られるその表層部分から計算されるガラス転移温度である第2のTgが40℃以上であり、且つ、前記第1のTgよりも30℃以上高い、
粘着剤組成物。
(2)前記第1のTgが−30℃以上5℃以下であり、
前記第2のTgが50℃以上180℃以下である、(1)に記載の粘着剤組成物。
(3)前記第1のTgが−25℃以上1℃以下であり、
前記第2のTgが70℃以上180℃以下である、(2)に記載の粘着剤組成物。
(4)前記アクリル系粘着性ポリマー(B)のガラス転移温度が−80℃以上10℃以下である、(1)〜(3)のいずれかに記載の粘着剤組成物。
(5)前記アクリル系粘着性ポリマー(B)のガラス転移温度が−30℃以上10℃以下である、(4)に記載の粘着剤組成物。
(6)前記アクリル系粘着性ポリマー(B)を構成する全単量体単位に対し、炭素数2〜4のアルコキシアルキル基を有する(メタ)アクリル酸アルコキシアルキルエステル及び炭素数1〜3のアルキル基を有する(メタ)アクリル酸アルキルエステルからなる群より選ばれる少なくとも1種の化合物を10質量%以上99質量%以下含む、(1)〜(5)のいずれかに記載の粘着剤組成物。
(7)前記アクリル系粘着性ポリマー(B)を構成する全単量体単位に対し、炭素数1〜4のアルキル基を有する(メタ)アクリル酸アルキルエステルを10質量%以上80質量%以下含む、(1)〜(6)のいずれかに記載の粘着剤組成物。
(8)前記粘着剤組成物からなる膜厚50μmの粘着剤層を100μm厚ポリエチレンテレフタレートフィルム基材に備えた粘着シートの100℃におけるガラス板に対する剥離強度が5.0N/25mm以上である、(1)〜(7)のいずれかに記載の粘着剤組成物。
(9)前記アクリル系粘着性ポリマー(B)100質量部に対し、前記ビニル重合体(A)を10質量部以上60質量部以下含有する、(1)〜(8)のいずれかに記載の粘着剤組成物。
(10)粘着剤層を備える粘着製品であって、
前記粘着剤層は、
ビニル重合体(A)及びアクリル系粘着性ポリマー(B)を含む粘着剤組成物を含み、
前記ビニル重合体(A)は、ガラス転移温度(Tg)が60℃以上200℃以下であり、数平均分子量が500以上10,000以下であって、前記アクリル系粘着性ポリマー(B)100質量部に対して0.5質量部以上60質量部以下含有し、
前記粘着剤組成物をセパレーターに塗工し、乾燥させて粘着剤層を得た際に、当該粘着剤層全体のガラス転移温度である第1のTgが−80℃以上10℃以下であり、
前記粘着剤層のX線光電子分光分析により得られるその表層部分から計算されるガラス転移温度である第2のTgが40℃以上であり、且つ、前記第1のTgよりも30℃以上高い、
粘着製品。
(11)基材の片面又は両面に、前記粘着剤層を備えた粘着シート又は粘着テープである、(10)に記載の粘着製品。
本粘着剤組成物は、ビニル重合体(A)及びアクリル系粘着性ポリマー(B)を含有するものである。当該ビニル重合体(A)、アクリル系粘着性ポリマー(B)及びこれらを含有する粘着剤組成物の詳細について、以下に順次説明する。
本発明のビニル重合体(A)は、60℃以上200℃以下のTgを備えることができる。Tgの範囲は、アクリル系粘着性ポリマー(B)のTgにもよるが、ビニル重合体(A)のTgが高い場合には、良好な耐熱性が得られ易い。Tgが60℃未満であると、高温条件下で各種被着体への接着強度が十分でなく耐久性に劣る場合がある。また、原料単量体の制約等から、一般に200℃を超えることはない。
不飽和ジカルボン酸のジアルキルエステルとしては、マレイン酸、フマル酸、イタコン酸、シトラコン酸、無水マレイン酸、無水イタコン酸、無水シトラコン酸等のジアルキルエステルが挙げられる。
単量体を含む各原料の仕込み方法は、すべての原料を一括して仕込むバッチ式の初期一括仕込みでもよく、少なくとも一つの原料を連続的に反応器中に供給するセミ連続仕込みでもよく、全原料を連続供給し、同時に反応器から連続的に生成樹脂を抜き出す連続重合方式でもよい。
また、レドックス型重合開始剤としては、亜硫酸ナトリウム、チオ硫酸ナトリウム、ナトリウムホルムアルデヒドスルホキシレート、アスコルビン酸、硫酸第一鉄等を還元剤とし、ペルオキソ二硫酸カリウム、過酸化水素、tert−ブチルハイドロパーオキサイド等を酸化剤としたものを用いることができる。
アクリル系粘着性ポリマー(B)は(メタ)アクリル酸エステル化合物を主要単量体単位として含むことができる。アクリル系粘着性ポリマー(B)の単量体単位については後述する。
上記Fedors法により求められる主な単量体の溶解パラメータ(SP値)を表1に例示する。
本粘着剤組成物は、上記ビニル重合体(A)と上記アクリル系粘着性ポリマー(B)とを所定の配合比で含有することができる。そして、これにより、本粘着剤組成物から粘着剤層を得た際に、ビニル重合体(A)を表層に偏析させることで、粘着剤層表面近傍のTgが高くなり、ひいては良好な耐熱性と接着強度を得ることができる。こうしたビニル重合体(A)の偏析挙動のほか、後述する粘着剤層表層と粘着剤層全体のTg差は、アクリル系粘着性ポリマー(B)に対するビニル重合体(A)の配合比、ビニル重合体(A)の単量体組成(極性)や分子量のほか、Tg、Mw/Mn等を適宜設定することにより調整することができる。
上記イソシアネート化合物としては、芳香族系、脂肪族系、脂環族系の各種イソシアネート化合物、更には、これらのイソシアネート化合物の変性物(プレポリマー等)を用いることができる。
脂肪族イソシアネートとしては、ヘキサメチレンジイソシアネート(HDI)、リシンジイソシアネート(LDI)、リシントリイソシアネート(LTI)等が挙げられる。
脂環族イソシアネートとしては、イソホロンジイソシアネート(IPDI)、シクロヘキシルジイソシアネート(CHDI)、水添化XDI(H6XDI)、水添化MDI(H12MDI)等が挙げられる。
また、変性イソシアネートとしては、上記イソシアネート化合物のウレタン変性体、2量体、3量体、カルボジイミド変性体、アロファネート変性体、ビューレット変性体、ウレア変性体、イソシアヌレート変性体、オキサゾリドン変性体、イソシアネート基末端プレポリマー等が挙げられる。
上記溶液型粘着剤組成物及びエマルション型粘着剤組成物の場合、用いられる有機溶剤または水等の媒体は、粘着剤組成物100質量部に対して通常20〜80質量部である。
光増感剤としては、安息香酸系及びアミン系光増感剤等が挙げられる。これらは、2種以上を組み合わせて用いることもできる。光重合開始剤及び光増感剤の使用量は、単官能及び/又は多官能の(メタ)アクリル酸系単量体100質量部に対して0.01質量部以上10質量部以下とすることもできる。
また、本実施例において得られた重合体の各種分析は、以下に記載の方法により実施した。
測定サンプル約1gを秤量(a)し、次いで、送風乾燥機155℃、30分間乾燥後の残分を測定(b)し、以下の式より算出した。測定には秤量ビンを使用した。その他の操作については、JIS K 0067−1992(化学製品の減量及び残分試験方法)に準拠した。
固形分(%)=(b/a)×100
分子量はGPCにて下記の条件で測定した。
GPC:東ソー(HLC−8120)
カラム:東ソー(TSKgel−Super MP−M×4本)
試料濃度:0.1%
流量:0.6ml/分
溶離液:テトラヒドロフラン
カラム温度:40℃
検出器:示差屈折計(RI)
標準物質:ポリスチレン
ビニル重合体(A)、アクリル系粘着性ポリマー(B)及び粘着剤層全体のTgはDSCにて以下の条件で測定した。
DSC:TA Instrument製(Q−100)
昇温温度:10℃/分
測定雰囲気:窒素
ポリマー組成はモノマー仕込量とGC測定によるモノマー消費量から算出した。
GC:Agilent Technolosies製(7820A GC System)
検出器:FID
カラム:100%ジメチルシロキサン(CP−Sil 5CB) 長さ30m、内径0.32mm
算出方法:内部標準法
合成例1(重合体A−1の合成)
内容積1リットルの4つ口フラスコに、酢酸ブチル200質量部とジメチル2,2’−アゾビス(2−メチルプロピオネート)(和光純薬社製、商品名「V−601」)0.9質量部とからなる混合液を仕込み、この混合液を窒素ガスのバブリングにより十分に脱気し、混合液の内温を90℃に上昇した。別途、メタクリル酸メチル(以下、「MMA」という)165質量部、メタクリル酸イソボルニル(以下、「IBXMA」という)44質量部、V−601 17質量部、酢酸ブチル90質量部からなる混合液を滴下ロートからフラスコ内に5時間かけて滴下することにより重合を行った。滴下終了後、重合溶液をメタノール4800質量部、蒸留水1200質量部からなる混合溶液に滴下することにより、重合溶液中のビニル重合体を単離して、重合体A−1を得た。得られた重合体A−1のポリマー組成は、仕込量とGC測定によるモノマー消費量から計算した結果、MMA 80質量%及びIBXMA 20質量%からなり、Mw6700、Mn4370、Mw/Mn1.53であった。Tgは108℃であった。重合体A−1の組成及び分析結果を表2に示す。
内容積1リットルの4つ口フラスコに、酢酸ブチル200質量部とV−601 0.6質量部とからなる混合液を仕込み、この混合液を窒素ガスのバブリングにより十分に脱気し、混合液の内温を90℃に上昇した。別途、MMA 165質量部、IBXMA 43質量部、V−601 11質量部、酢酸ブチル90質量部からなる混合液を滴下ロートからフラスコ内に5時間かけて滴下することにより重合を行った。滴下終了後、重合溶液をメタノール4800質量部、蒸留水1200質量部からなる混合溶液に滴下することにより、重合溶液中のビニル重合体を単離して、重合体A−2を得た。重合体A−2の組成及び分析結果を表2に示す。
内容積1リットルの4つ口フラスコに、酢酸ブチル200質量部とV−601 4.1質量部とからなる混合液を仕込み、この混合液を窒素ガスのバブリングにより十分に脱気し、混合液の内温を90℃に上昇した。別途、MMA 168質量部、IBXMA 83質量部、V−601 78質量部、酢酸ブチル90質量部からなる混合液を滴下ロートからフラスコ内に5時間かけて滴下することにより重合を行った。滴下終了後、重合溶液をメタノール4800質量部、蒸留水1200質量部からなる混合溶液に滴下することにより、重合溶液中のビニル重合体を単離して、重合体A−3を得た。重合体A−3の組成及び分析結果を表2に示す。
内容積1リットルの4つ口フラスコに、酢酸ブチル200質量部とV−601 0.9質量部とからなる混合液を仕込み、この混合液を窒素ガスのバブリングにより十分に脱気し、混合液の内温を90℃に上昇した。別途、MMA 60質量部、IBXMA 166質量部、V−601 18質量部、酢酸ブチル90質量部からなる混合液を滴下ロートからフラスコ内に5時間かけて滴下することにより重合を行った。滴下終了後、重合溶液をメタノール4800質量部、蒸留水1200質量部からなる混合溶液に滴下することにより、重合溶液中のビニル重合体を単離して、重合体A−4を得た。重合体A−4の組成及び分析結果を表2に示す。
内容積1リットルの4つ口フラスコに、酢酸ブチル280質量部、V−601 0.3質量部からなる混合液を仕込み、この混合液を窒素ガスのバブリングにより十分に脱気し、混合液の内温を90℃に上昇した。別途、MMA233質量部、IBXMA26質量部、V−601 5.1質量部、酢酸ブチル90質量部からなる混合液を滴下ロートからフラスコ内に5時間かけて滴下することにより重合を行った。滴下終了後、重合溶液をヘキサン6000質量部に滴下することにより、重合溶液中のビニル重合体を単離して、重合体A−5を得た。 重合体A−5の組成及び分析結果を表2に示す。
内容積1リットルの4つ口フラスコに、酢酸ブチル200質量部、V−601 6.2質量部からなる混合液を仕込み、この混合液を窒素ガスのバブリングにより十分に脱気し、混合液の内温を90℃に上昇した。別途、MMA114質量部、IBXMA140質量部、V−601 110質量部、酢酸ブチル90質量部からなる混合液を滴下ロートからフラスコ内に5時間かけて滴下することにより重合を行った。滴下終了後、重合溶液をメタノール4800質量部、蒸留水1200質量部からなる混合溶液に滴下することにより、重合溶液中のビニル重合体を単離して、重合体A−6を得た。重合体A−6の組成及び分析結果を表2に示す。
内容積1リットルの4つ口フラスコに、酢酸ブチル200質量部とV−601 1.8質量部とからなる混合液を仕込み、この混合液を窒素ガスのバブリングにより十分に脱気し、混合液の内温を90℃に上昇した。別途、MMA155質量部、IBXMA55質量部、V−601 35質量部、酢酸ブチル90質量部からなる混合液を滴下ロートからフラスコ内に5時間かけて滴下することにより重合を行った。滴下終了後、重合溶液をメタノール4200質量部、蒸留水1800質量部からなる混合溶液に滴下することにより、重合溶液中のビニル重合体を単離して、重合体A−7を得た。重合体A−7の組成及び分析結果を表2に示す。
合成例8(重合体B−1の合成)
内容積3リットルの4つ口フラスコに、アクリル酸メトキシエチル(以下、「MEA」という)(500質量部)、アクリル酸2−ヒドロキシエチル(以下、「HEA」という)(27質量部)、酢酸エチル(980質量部)を仕込み、この混合液を窒素ガスのバブリングにより十分に脱気し、混合液の内温を75℃に上昇し、アゾビスバレロニトリル(以下、「V−65」という)(0.25質量部)を仕込み重合を開始した。5時間後、酢酸エチルを固形分が30質量%になるように追加して、重合体B−1の酢酸エチル溶液を得た。得られた重合体B−1は、MEA95質量%、HEA5質量%とからなり、Mw520000、Mn116000、Mw/Mn4.48であった。重合体B−1の組成及び分析結果を表3に示す。
内容積3リットルの4つ口フラスコに、MEA(413質量部)、HEA(27質量部)、アクリル酸ブチル(以下、「BA」という)(90質量部)、酢酸エチル(980質量部)を仕込み、この混合液を窒素ガスのバブリングにより十分に脱気し、混合液の内温を75℃に上昇し、V−65(0.25質量部)を仕込み重合を開始した。5時間後、酢酸エチルを固形分が30質量%になるように追加して、重合体B−2の酢酸エチル溶液を得た。重合体B−2の組成及び分析結果を表3に示す。
内容積3リットルの4つ口フラスコに、MEA(254質量部)、HEA(27質量部)、BA(90質量部)、アクリル酸メチル(以下、「MA」という)(159質量部)、酢酸エチル(980質量部)を仕込み、この混合液を窒素ガスのバブリングにより十分に脱気し、混合液の内温を75℃に上昇し、V−65(0.20質量部)を仕込み重合を開始した。5時間後、酢酸エチルを固形分が30質量%になるように追加して、重合体B−3の酢酸エチル溶液を得た。重合体B−3の組成及び分析結果を表3に示す。
内容積3リットルの4つ口フラスコに、HEA(27質量部)、BA(192質量部)、MA(330質量部)、酢酸エチル(1200質量部)を仕込み、この混合液を窒素ガスのバブリングにより十分に脱気し、混合液の内温を75℃に上昇し、V−65(0.23質量部)を仕込み重合を開始した。5時間後、酢酸エチルを固形分が30質量%になるように追加して、重合体B−4の酢酸エチル溶液を得た。重合体B−4の組成及び分析結果を表3に示す。
内容積3リットルの4つ口フラスコに、MEA(105質量部)、HEA(25質量部)、BA(370質量部)、酢酸エチル(930質量部)を仕込み、この混合液を窒素ガスのバブリングにより十分に脱気し、混合液の内温を75℃に上昇し、V−65(0.24質量部)を仕込み重合を開始した。5時間後、酢酸エチルを固形分が30質量%になるように追加して、重合体B−5の酢酸エチル溶液を得た。重合体B−5の組成及び分析結果を表3に示す。
内容積3リットルの4つ口フラスコに、HEA(20質量部)、BA(140質量部)、MA(240質量部)、酢酸エチル(600質量部)を仕込み、この混合液を窒素ガスのバブリングにより十分に脱気し、混合液の内温を75℃に上昇し、V−65(0.10質量部)を仕込み重合を開始した。5時間後、酢酸エチルを固形分が30質量%になるように追加して、重合体B−6の酢酸エチル溶液を得た。重合体B−6の組成及び分析結果を表3に示す。
実施例1
上記合成例1で得られた重合体(A−1)を酢酸エチルに溶解して固形分濃度30質量%の重合体(A−1)溶液を調整した。当該重合体(A−1)溶液2質量部、重合体B−1溶液(100質量部)、架橋剤としてタケネートD−110N(固形分濃度75質量%、三井化学社製)(0.16質量部)を混合し、粘着剤組成物を得た。
粘着フィルム試料から粘着剤を0.2g採取し、粘着剤の初期重量を秤量した。その粘着剤を50gの酢酸エチルに浸漬し、室温で16時間静置した。その後、200メッシュ金網でろ過し、メッシュに残った残分を80℃で3時間乾燥し、秤量した。初期の重量と残分の重量から、下式によりアクリル系粘着性ポリマー(B)に基づくゲル分率を算出した。
粘着フィルム試料から剥離フィルムを剥がし、ガラスプレート(1mm厚)に転写し、もう一方の剥離フィルムを剥がした。23℃、50%RH条件下で1日静置した後、日本電色社製ヘイズメーター「ヘイズメーターNDH2000」(型式名)を使用してヘイズ値を測定することにより、その配合組成における透明性を評価した。
粘着フィルム試料を用いてボールタックに関して評価した。ボールタックはJISZ0237に準じて評価した。
粘着フィルム試料を易接着処理したPETフィルム(100μm)に転写して評価用の粘着シートを得た。被着体をガラス板(旭硝子社製、ファブリテックFL11A、1mm厚)とし、上記評価用の粘着シートを貼り合せ、2kgローラーで3往復圧着した後、恒温槽付き引張り試験機ストログラフR型(東洋精機社製)を用いて、23℃で、JIS Z−0237「粘着テープ・粘着シート試験方法」に準じて粘着シートの180度剥離強度を測定し、剥離強度とした。尚、剥離速度は300mm/min.とした。
粘着フィルム試料を易接着処理したPETフィルム(100μm)に転写して評価用の粘着シートを得た。被着体をガラス板(旭硝子社製、ファブリテックFL11A、1mm厚)とし、上記評価用の粘着シートを貼り合せ、卓上加圧脱泡装置TBR−200(千代田電気工業社製)を用いて0.5MPa、50℃の条件下で20分間圧着した後、恒温槽付き引張り試験機ストログラフR型(東洋精機社製)を用いて、85℃、100℃及び120℃の条件で、JIS Z−0237「粘着テープ・粘着シート試験方法」に準じて粘着シートの180度剥離強度を測定し、剥離強度とした。尚、剥離速度は300mm/min.とした。
粘着フィルム試料のX線光電子分光装置(XPS)測定によるO1sとC1sのピーク面積比から、粘着剤層の表層部分におけるビニル重合体(A)及びアクリル系粘着性ポリマー(B)の総量に対する、ビニル重合体(A)及びアクリル系粘着性ポリマー(B)の各質量分率(wA及びwB)を算出し、FOXの式に基づき表層部分のTgを算出した。
尚、XPS測定は以下の条件で測定した。
装置: アルバック・ファイ社製 PHI5000 VersaProbe
X線: Al−Kα (1486.6eV)
試料へのX線入射角: 0° (試料測定面の法線に対する角度)
光電子検出角: 45° (試料測定面の法線に対する角度)
XPS測定によるO1sとC1sのピーク面積比から算出される酸素原子数と炭素原子数の比は、下式(1)の通り、ビニル重合体(A)及びアクリル系粘着性ポリマー(B)からなる粘着剤組成物から形成された粘着剤層表層部の単位重量当りに存在する酸素原子数と炭素原子数の比で表される。
(O/C)A+B:粘着剤組成物を乾燥して得られた粘着剤層のXPS測定から求められるO1sとC1sのピーク面積比から算出される酸素原子数と炭素原子数の比
WA:ビニル重合体(A)及びアクリル系粘着性ポリマー(B)の総量に対するビニル重合体(A)の質量分率
Mw-A:ビニル重合体(A)の全構成単量体単位の加重平均分子量
Mw-B:アクリル系粘着剤組成物(B)の全構成単量体単位の加重平均分子量
NO-A:ビニル重合体(A)を構成する全構成単量体の平均単量体構造式中に含まれる酸素原子数
NO-B:アクリル系粘着性ポリマー(B)を構成する全構成単量体の平均単量体構造式中に含まれる酸素原子数
NC-A:ビニル重合体(A)を構成する全構成単量体の平均単量体構造式中に含まれる炭素原子数
NC-B:アクリル系粘着性ポリマー(B)を構成する全構成単量体の平均単量体構造式中に含まれる炭素原子数
(O/C)A:ビニル重合体(A)を乾燥して得られたフィルムのXPS測定から求められるO1sとC1sのピーク面積比から算出される酸素原子数と炭素原子数の比
(O/C)B:アクリル系粘着性ポリマー(B)を乾燥して得られたフィルムのXPS測定から求められるO1sとC1sのピーク面積比から算出される酸素原子数と炭素原子数の比
WB:ビニル重合体(A)及びアクリル系粘着性ポリマー(B)の総量に対するアクリル系粘着性ポリマー(B)の質量分率
(O/C)A+B:0.340(実測値)
(O/C)A:0.290(実測値)
(O/C)B:0.474(実測値)
NC-A:MMA1分子中の炭素原子数(5)、IBXMA1分子中の炭素原子数(14)及び組成比より、5×89.9(mol%)+14×10.1(mol%)=5.91
NC-B:MEA1分子中の炭素原子数(6)、HEA1分子中の炭素原子数(5)及び組成比より、6×94.4(mol%)+5×5.6(mol%)=5.94
Mw-A:MMAの分子量(100)、IBXMAの分子量(222)及び組成比より、100×89.9(mol%)+222×10.1(mol%)=112.3
Mw-B:MEAの分子量(130)、HEAの分子量(116)及び組成比より、130×94.4(mol%)+116×5.6(mol%)=129.2
これらの値を式(4)に代入することによりWA=0.703が得られ、(5)式よりWB=0.297が得られた。
1/〔表層部分のTg〕(K)=WA/TgA+WB/TgB (6)
ここで、
TgA:ビニル重合体(A)のTg(70.3℃)
TgB:アクリル系粘着性ポリマー(B)のTg(−31℃)
粘着フィルム試料の片面に厚さ100μmの易接着処理したPETフィルムを貼り付け、他方の面にポリカーボネート板を貼り付けた積層体を作成し、前記積層体に50℃、0.5MPa、20分の圧着処理を行った。その後、積層体に恒温恒湿槽を用いて85℃/85%RHで24時間、又は、送風乾燥機を用いて100℃で24時間、若しくは120℃で20分間の各条件で負荷を与え、負荷後の外観(発泡の有無)を目視で確認し、以下の基準に従って評価した。
○:外観変化なし
△:試験片の面積に対し発泡を生じた部分の面積が10%以下
×:試験片の面積に対し発泡を生じた部分の面積が10%超
実施例1において、アクリル系粘着性ポリマー及びビニル重合体の種類、比率を表4及び表5に示すように変えて粘着剤組成物を得るとともに、実施例1と同様の測定を行った。結果を表4及び表5に示す。
Claims (9)
- ビニル重合体(A)及びアクリル系粘着性ポリマー(B)を含む粘着剤組成物であって、
前記ビニル重合体(A)は、ガラス転移温度(Tg)が60℃以上200℃以下であり、数平均分子量が500以上10,000以下であって、前記アクリル系粘着性ポリマー(B)100質量部に対して0.5質量部以上60質量部以下含有し、
前記アクリル系粘着性ポリマー(B)のガラス転移温度が−30℃以上10℃以下であり、
前記粘着剤組成物をセパレーターに塗工し、乾燥させて粘着剤層を得た際に、当該粘着剤層全体のガラス転移温度である第1のTgが−80℃以上10℃以下であり、
前記粘着剤層のX線光電子分光分析により得られるその表層部分から計算されるガラス転移温度である第2のTgが40℃以上であり、且つ、前記第1のTgよりも30℃以上高い、
粘着剤組成物。 - 前記第1のTgが−30℃以上5℃以下であり、
前記第2のTgが50℃以上180℃以下である、請求項1に記載の粘着剤組成物。 - 前記第1のTgが−25℃以上1℃以下であり、
前記第2のTgが70℃以上180℃以下である、請求項2に記載の粘着剤組成物。 - 前記アクリル系粘着性ポリマー(B)を構成する全単量体単位に対し、炭素数2〜4のアルコキシアルキル基を有する(メタ)アクリル酸アルコキシアルキルエステル及び炭素数1〜3のアルキル基を有する(メタ)アクリル酸アルキルエステルからなる群より選ばれる少なくとも1種の化合物を10質量%以上99質量%以下含む、請求項1〜3のいずれかに記載の粘着剤組成物。
- 前記アクリル系粘着性ポリマー(B)を構成する全単量体単位に対し、炭素数1〜3のアルキル基を有する(メタ)アクリル酸アルキルエステルを10質量%以上80質量%以下含む、請求項1〜4のいずれかに記載の粘着剤組成物。
- 前記粘着剤組成物からなる膜厚50μmの粘着剤層を100μm厚ポリエチレンテレフタレートフィルム基材に備えた粘着シートの100℃におけるガラス板に対する剥離強度が5.0N/25mm以上である、請求項1〜5のいずれかに記載の粘着剤組成物。
- 前記アクリル系粘着性ポリマー(B)100質量部に対し、前記ビニル重合体(A)を10質量部以上60質量部以下含有する、請求項1〜6のいずれかに記載の粘着剤組成物。
- 粘着剤層を備える粘着製品であって、
前記粘着剤層は、
ビニル重合体(A)及びアクリル系粘着性ポリマー(B)を含む粘着剤組成物を含み、
前記ビニル重合体(A)は、ガラス転移温度(Tg)が60℃以上200℃以下であり、数平均分子量が500以上10,000以下であって、前記アクリル系粘着性ポリマー(B)100質量部に対して0.5質量部以上60質量部以下含有し、
前記アクリル系粘着性ポリマー(B)のガラス転移温度が−30℃以上10℃以下であり、
前記粘着剤組成物をセパレーターに塗工し、乾燥させて粘着剤層を得た際に、当該粘着剤層全体のガラス転移温度である第1のTgが−80℃以上10℃以下であり、
前記粘着剤層のX線光電子分光分析により得られるその表層部分から計算されるガラス転移温度である第2のTgが40℃以上であり、且つ、前記第1のTgよりも30℃以上高い、
粘着製品。 - 基材の片面又は両面に、前記粘着剤層を備えた粘着シート又は粘着テープである、請求項8に記載の粘着製品。
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