JP2017171771A - 活性エネルギー線硬化型組成物 - Google Patents
活性エネルギー線硬化型組成物 Download PDFInfo
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- JP2017171771A JP2017171771A JP2016058852A JP2016058852A JP2017171771A JP 2017171771 A JP2017171771 A JP 2017171771A JP 2016058852 A JP2016058852 A JP 2016058852A JP 2016058852 A JP2016058852 A JP 2016058852A JP 2017171771 A JP2017171771 A JP 2017171771A
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- Prior art keywords
- meth
- active energy
- mgkoh
- energy ray
- curable composition
- Prior art date
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- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- ZLSMCQSGRWNEGX-UHFFFAOYSA-N bis(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(N)C=C1 ZLSMCQSGRWNEGX-UHFFFAOYSA-N 0.000 description 1
- RFVHVYKVRGKLNK-UHFFFAOYSA-N bis(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=C(OC)C=C1 RFVHVYKVRGKLNK-UHFFFAOYSA-N 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 210000000038 chest Anatomy 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- DKKXSNXGIOPYGQ-UHFFFAOYSA-N diphenylphosphanyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(C=1C=CC=CC=1)C1=CC=CC=C1 DKKXSNXGIOPYGQ-UHFFFAOYSA-N 0.000 description 1
- PODOEQVNFJSWIK-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC(OC)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 PODOEQVNFJSWIK-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000007610 electrostatic coating method Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- FSPSELPMWGWDRY-UHFFFAOYSA-N m-Methylacetophenone Chemical compound CC(=O)C1=CC=CC(C)=C1 FSPSELPMWGWDRY-UHFFFAOYSA-N 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920005650 polypropylene glycol diacrylate Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
- RGBXDEHYFWDBKD-UHFFFAOYSA-N propan-2-yl propan-2-yloxy carbonate Chemical compound CC(C)OOC(=O)OC(C)C RGBXDEHYFWDBKD-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 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
- 239000013638 trimer Substances 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-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
- 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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
- C08G18/673—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen containing two or more acrylate or alkylacrylate ester groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/81—Unsaturated isocyanates or isothiocyanates
- C08G18/8125—Unsaturated isocyanates or isothiocyanates having two or more isocyanate or isothiocyanate groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/81—Unsaturated isocyanates or isothiocyanates
- C08G18/8141—Unsaturated isocyanates or isothiocyanates masked
- C08G18/815—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen
- C08G18/8158—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with unsaturated compounds having only one group containing active hydrogen
- C08G18/8175—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with unsaturated compounds having only one group containing active hydrogen with esters of acrylic or alkylacrylic acid having only one group containing active hydrogen
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- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
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- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
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- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
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- Macromonomer-Based Addition Polymer (AREA)
- Polyurethanes Or Polyureas (AREA)
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Abstract
Description
温度計、撹拌機、水冷コンデンサーを備えた4つ口フラスコに、アクリル酸1,151部(16.0モル)、ペンタエリスリトール(広栄化学工業株式会社)604部(4.44モル)、パラトルエンスルホン酸43.9部、ハイドロキノンモノメチルエーテル2.1部、トルエン552部を混合し、空気を吹き込みながら反応温度約100℃を維持できるように減圧下の条件で、ペンタエリスリトール中の全水酸基の58%がエステル化されるまで反応させた。反応は縮合水を除去しながら行い、発生した縮合水は179部であった。反応終了後に、トルエン353部を追加した。このトルエンを追加した反応液の酸分に対して1.1倍モル量に相当する20質量%水酸化ナトリウム水溶液を撹拌下に添加して中和処理を実施し、過剰なアクリル酸及びパラトルエンスルホン酸を除去した。有機層を分離し、撹拌下で有機層100部に対して水10部を添加し水洗処理を行った。有機層を分離し、減圧下に加熱してトルエンを留去した。得られたアクリル酸エステルは837部であり、水酸基価は190mgKOH/gであった。
温度計、撹拌機、水冷コンデンサーを備えた4つ口フラスコに、アクリル酸1,151部(16.0モル)、ペンタエリスリトール(広栄化学工業株式会社)604部(4.44モル)、パラトルエンスルホン酸43.9部、ハイドロキノンモノメチルエーテル2.1部、トルエン552部を混合し、空気を吹き込みながら反応温度約100℃を維持できるように減圧下の条件で、ペンタエリスリトール中の全水酸基の58%がエステル化されるまで反応させた。反応は縮合水を除去しながら行い、発生した縮合水は179部であった。反応終了後に、トルエン353部を追加した。このトルエンを追加した反応液の酸分に対して1.4倍モル量に相当する20質量%水酸化ナトリウム水溶液を撹拌下に添加して中和処理を実施し、過剰なアクリル酸及びパラトルエンスルホン酸を除去した。有機層を分離し、撹拌下で有機層100部に対して水10部を添加し水洗処理を行った。有機層を分離し、減圧下に加熱してトルエンを留去した。得られたアクリル酸エステルは837部であり、水酸基価は165mgKOH/gであった。
温度計、撹拌機、水冷コンデンサーを備えた4つ口フラスコに、アクリル酸1,151部(16.0モル)、ペンタエリスリトール(広栄化学工業株式会社)604部(4.44モル)、パラトルエンスルホン酸43.9部、ハイドロキノンモノメチルエーテル2.1部、トルエン552部を混合し、空気を吹き込みながら反応温度約100℃を維持できるように減圧下の条件で、ペンタエリスリトール中の全水酸基の80%がエステル化されるまで反応させた。反応は縮合水を除去しながら行い、発生した縮合水は256部であった。反応終了後に、トルエン353部を追加した。このトルエンを追加した反応液の酸分に対して1.4倍モル量に相当する20質量%水酸化ナトリウム水溶液を撹拌下に添加して中和処理を実施し、過剰なアクリル酸及びパラトルエンスルホン酸を除去した。有機層を分離し、撹拌下で有機層100部に対して水10部を添加し水洗処理を行った。有機層を分離し、減圧下に加熱してトルエンを留去した。得られたアクリル酸エステルは1082部であり、水酸基価は120mgKOH/gであった。
フラスコにヘキサメチレンジイソシアネート(旭化成ケミカルズ株式会社)168g(1モル)、ハイドロキノンモノメチルエーテル0.44g、上記合成例1で得られた水酸基価190mgKOH/gのペンタエリスリトールのアクリル酸エステル532g(1.8モル)と(2−アクリロイルオキシエチル)ヒドロキシエチルイソシアヌレート/2−アクリロイルオキシエチルイソシアヌレート混合物(質量比=56/44混合物、東亞合成株式会社製「アロニックスM−215」)187g(0.4モル)を仕込み、70〜80℃にて遊離イソシアネート量が0.1%以下になるまで反応させ、ウレタンアクリレートA(U−A)を得た。
フラスコにイソホロンジイソシアネート(エボニックジャパン株式会社)222g(1モル)、ハイドロキノンモノメチルエーテル0.44g、上記合成例1で得られた水酸基価190mgKOH/gのペンタエリスリトールのアクリル酸エステル532g(1.8モル)と(2−アクリロイルオキシエチル)ヒドロキシエチルイソシアヌレート/2−アクリロイルオキシエチルイソシアヌレート混合物(質量比=56/44混合物、東亞合成株式会社製「アロニックスM−215」)187g(0.4モル)を仕込み、70〜80℃にて遊離イソシアネート量が0.1%以下になるまで反応させ、ウレタンアクリレートB(U−B)を得た。
フラスコにノルボルネンジイソシアネート(三井化学株式会社)206g(1モル)、ハイドロキノンモノメチルエーテル0.44g、上記合成例2で得られた水酸基価163mgKOH/gのペンタエリスリトールのアクリル酸エステル532g(1.8モル)と(2−アクリロイルオキシエチル)ヒドロキシエチルイソシアヌレート/2−アクリロイルオキシエチルイソシアヌレート混合物(質量比=56/44混合物、東亞合成株式会社製「アロニックスM−215」)187g(0.4モル)を仕込み、70〜80℃にて遊離イソシアネート量が0.1%以下になるまで反応させ、ウレタンアクリレートC(U−C)を得た。
フラスコにイソホロンジイソシアネート(エボニックジャパン株式会社)222g(1モル)、ハイドロキノンモノメチルエーテル0.44g、上記合成例1で得られた水酸基価190mgKOH/gのペンタエリスリトールのアクリル酸エステル325g(1.1モル)と(2−アクリロイルオキシエチル)ヒドロキシエチルイソシアヌレート/2−アクリロイルオキシエチルイソシアヌレート混合物(質量比=56/44混合物、東亞合成株式会社製「アロニックスM−215」)514g(1.1モル)を仕込み、70〜80℃にて遊離イソシアネート量が0.1%以下になるまで反応させ、ウレタンアクリレートD(U−D)を得た。
フラスコにイソホロンジイソシアネート(エボニックジャパン株式会社)222g(1モル)、ハイドロキノンモノメチルエーテル0.44g、上記合成例3で得られた水酸基価120mgKOH/gのペンタエリスリトールのアクリル酸エステル1028g(2.2モル)を仕込み、70〜80℃にて遊離イソシアネート量が0.1%以下になるまで反応させ、ウレタンアクリレートE(U−E)を得た。
フラスコにイソホロンジイソシアネート(エボニックジャパン株式会社)222g(1モル)、ハイドロキノンモノメチルエーテル0.44g、上記合成例3で得られた水酸基価120mgKOH/gのペンタエリスリトールのアクリル酸エステル514g(1.1モル)と(2−アクリロイルオキシエチル)ヒドロキシエチルイソシアヌレート/2−アクリロイルオキシエチルイソシアヌレート混合物(質量比=56/44混合物、東亞合成株式会社製「アロニックスM−215」)514g(1.1モル)を仕込み、70〜80℃にて遊離イソシアネート量が0.1%以下になるまで反応させ、ウレタンアクリレートF(U−F)を得た。
表2に示す割合で配合された、上記合成例で得られたウレタンアクリレート(U−A〜F)と、多官能(メタ)アクリレート化合物又はその他(メタ)アクリレートの合計量各100質量部に対して、光重合開始剤(チバ・スペシャルティ・ケミカルズ社製 イルガキュア184)を3質量部それぞれ配合し、溶解した。これをポリエチレンテレフタレート基材(東洋紡株式会社製PET、型番:コスモシャインA4300)上に膜厚が約7μmになるように塗布し、高圧水銀ランプ80W/cmを用いて、積算照度600mJ/cm2にて、窒素雰囲気下にて照射し硬化させた。
JIS K5400に準じ、鉛筆引っかき試験機で荷重750gかけて引っかき、傷の付かない最も硬い鉛筆の硬さとした。
上記で得られたフィルムをJIS K5701−1に準じ、摩擦試験機(大平理化工業株式会社)を用い、スチールウール#0000を1kg荷重で100往復させた。試験前後の試験用フィルムのヘーズ値をヘーズメーター(日本電色工業株式会社製「NDH4000」)を用いて測定し、両値の差で評価した。数値は低いものほど耐擦傷性が良いことを示す。
試験用フィルムを10cm×10cmの大きさに切り出したものを水平面上に置き、1隅を固定して、水平面からの3隅の浮き(mm)をそれぞれ測定し、その平均値で評価した。数値が低いものほど成形性が良いことを示す。
本発明が含有するウレタン(メタ)アクリレートは、(A)水酸基価が160mgKOH/g以上220mgKOH/g以下である、3価以上の脂肪族多価アルコール化合物の(メタ)アクリル酸付加物と、(B)(2−(メタ)アクリロイルオキシエチル)ヒドロキシエチルイソシアヌレートと、(C)有機イソシアネート化合物との反応生成物であり、その構造は複雑であるため、一般式で表すことは困難である。さらに、構造が特定されなければ、それに応じて定まるその物質の特性も容易には特定できない。また、異なる複数のモノマーを反応させるにあたり、それらの配合比、反応条件が異なれば、得られる反応生成物の特性も大きく異なる。すなわち、本発明が含有するウレタン(メタ)アクリレートを、その構造又は特性により直接特定することは不可能である。
Claims (7)
- (A)水酸基価が160mgKOH/g以上220mgKOH/g以下である、3価以上の脂肪族多価アルコール化合物の(メタ)アクリル酸付加物と、
(B)(2−(メタ)アクリロイルオキシエチル)ヒドロキシエチルイソシアヌレートと、
(C)有機イソシアネート化合物との反応生成物であるウレタン(メタ)アクリレートを含有することを特徴とする活性エネルギー線硬化型組成物。 - (A)水酸基価が160mgKOH/g以上220mgKOH/g以下である、3価以上の脂肪族多価アルコール化合物の(メタ)アクリル酸付加物の3価以上の脂肪族多価アルコール化合物が、3価以上6価以下の脂肪族多価アルコールであることを特徴とする、請求項1に記載の活性エネルギー線硬化型組成物。
- (A)水酸基価が160mgKOH/g以上220mgKOH/g以下である、3価以上の脂肪族多価アルコール化合物の(メタ)アクリル酸付加物の3価以上の脂肪族多価アルコール化合物がペンタエリスリトールであることを特徴とする、請求項2に記載の活性エネルギー線硬化型組成物。
- (C)有機イソシアネート化合物が、ヘキサメチレンジイソシアネート、イソホロンジイソシアネート、及びノルボルネンジイソシアネートからなる群より選択された1種又は2種以上であることを特徴とする、請求項1〜3のいずれか1項に記載の活性エネルギー線硬化型組成物。
- (D)1分子中に3個以上の(メタ)アクリロイル基を有する多官能(メタ)アクリレートをさらに含有することを特徴とする、請求項1〜4のいずれか1項に記載の活性エネルギー線硬化型組成物。
- 前記(A)成分と(B)成分との割合((A)/(B))が、質量比で、95/5〜50/50であることを特徴とする、請求項1〜5のいずれかの1項に記載の活性エネルギー線硬化型組成物。
- 水酸基価から計算される(A)成分と(B)成分の水酸基の合計のモル数(a+b)と(C)成分のイソシアネート基のモル数(c)とのモル比((a+b)/c)が、0.5以上、1未満であることを特徴とする、請求項1〜6のいずれかの1項に記載の活性エネルギー線硬化型組成物。
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