JPWO2018097147A1 - 硬化性組成物、その硬化物およびその硬化方法 - Google Patents
硬化性組成物、その硬化物およびその硬化方法 Download PDFInfo
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- JPWO2018097147A1 JPWO2018097147A1 JP2018552599A JP2018552599A JPWO2018097147A1 JP WO2018097147 A1 JPWO2018097147 A1 JP WO2018097147A1 JP 2018552599 A JP2018552599 A JP 2018552599A JP 2018552599 A JP2018552599 A JP 2018552599A JP WO2018097147 A1 JPWO2018097147 A1 JP WO2018097147A1
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- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- FUPZEKMVZVPYLE-UHFFFAOYSA-N prop-2-enoic acid;prop-2-enylbenzene Chemical compound OC(=O)C=C.C=CCC1=CC=CC=C1 FUPZEKMVZVPYLE-UHFFFAOYSA-N 0.000 description 1
- IKNCGYCHMGNBCP-UHFFFAOYSA-N propan-1-olate Chemical compound CCC[O-] IKNCGYCHMGNBCP-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002834 transmittance Methods 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
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- XREXPQGDOPQPAH-QKUPJAQQSA-K trisodium;[(z)-18-[1,3-bis[[(z)-12-sulfonatooxyoctadec-9-enoyl]oxy]propan-2-yloxy]-18-oxooctadec-9-en-7-yl] sulfate Chemical compound [Na+].[Na+].[Na+].CCCCCCC(OS([O-])(=O)=O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(CCCCCC)OS([O-])(=O)=O)COC(=O)CCCCCCC\C=C/CC(CCCCCC)OS([O-])(=O)=O XREXPQGDOPQPAH-QKUPJAQQSA-K 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003755 zirconium compounds Chemical class 0.000 description 1
Classifications
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- 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
- C08F261/00—Macromolecular compounds obtained by polymerising monomers on to polymers of oxygen-containing monomers as defined in group C08F16/00
- C08F261/02—Macromolecular compounds obtained by polymerising monomers on to polymers of oxygen-containing monomers as defined in group C08F16/00 on to polymers of unsaturated alcohols
- C08F261/04—Macromolecular compounds obtained by polymerising monomers on to polymers of oxygen-containing monomers as defined in group C08F16/00 on to polymers of unsaturated alcohols on to polymers of vinyl alcohol
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
- C08F290/12—Polymers provided for in subclasses C08C or C08F
- C08F290/126—Polymers of unsaturated carboxylic acids or derivatives thereof
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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
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
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- Wood Science & Technology (AREA)
- Materials For Photolithography (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Abstract
Description
(式中、R1は、水素原子、メチル基またはハロゲン原子であり、X1は、炭素原子数1〜6の水酸基で置換されていてもよいアルキレン基を表し、Aは、n価の有機基であり、mは、1〜30の数であり、nは、2〜12の数である。)で表される化合物であることが好ましく、前記水溶性多官能(メタ)アクリルアミドは、下記一般式(II)、
(式中、R11は、水素原子または炭素原子数1〜4のアルキル基を表し、tは、2〜12の数であり、R1およびAは、上記一般式(I)と同じである。)で表される化合物であることが好ましい。また、本発明の硬化性組成物においては、前記感光性基を有する水溶性重合体(B)が、下記一般式(III)、または(IV)、
(式中、Yは、2価の有機基を表し、Qは感光性基を表す。)で表される構成単位を含む水溶性重合体、または、下記一般式(V)、
(式中、Anq−はq価のアニオンを表し、qは1または2を表し、pは電荷を中性に保つ係数である。)で表される構成単位を含む水溶性重合体であることが好ましい。さらに、本発明の硬化性組成物においては、前記一般式(III)および(IV)において、Qは、ビニル基、アリル基、スチリル基、シンナミル基、シンナモイル基、シンナミリデン基、シンナミリデンアセチル基、カルコン基、クマリン基、イソクマリン基、2,5−ジメトキシスチルベン基、マレイミド基、α−フェニルマレイミド基、2−ピロン基、アジド基、チミン基、キノン基、マレイミド基、ウラシル基、ピリミジン基、スチルバゾリウム基、スチリルピリジニウム基、スチリルキノリウム基、エポキシ基、オキセタン基、ビニルエーテル基、アリルエーテル基、アセチルアセトン構造またはβ−ジケトン構造であるとが好ましい。さらにまた、本発明の硬化性組成物においては、前記感光性基を有する水溶性重合体(B)は、ポリビニルアルコールに(メタ)アクリレートまたは(メタ)アクリルアミド構造を導入したポリビニルアルコール誘導体であることが好ましい。また、本発明の硬化性組成物においては、さらに、ラジカル開始剤を含有することが好ましい。
本発明の硬化性組成物の(A)成分に係る水溶性多官能(メタ)アクリレートは、水に溶解する多官能(メタ)アクリレート、水分散して乳化する多官能(メタ)アクリレート、あるいはアルカリ水に溶解する多官能(メタ)アクリレートが挙げられ、構造としては、親水性の官能基であるエチレンオキサイド基、プロピレンオキサイド基、水酸基およびカルボキシル基からなる群より選ばれる一種類以上の基を分子内に有するもの、あるいはエチレンオキサイド変性、プロピレンオキサイド変性したものが挙げられる。ここで、(メタ)アクリレートとは、アクリレートおよびメタクリレートを意味する。
ここで、一般式(1)中、X2は、単結合、−CR30R31−、−NR32−、二価の炭素原子数1〜35の脂肪族炭化水素基、炭素原子数6〜35の芳香族炭化水素基若しくは炭素原子数2〜35の複素環基、または、下記式(2)〜(4)で表されるいずれかの置換基を表し、脂肪族炭化水素基は、−O−、−S−、−CO−、−COO−、−OCO−または−NH−、あるいは酸素原子が隣り合うことなしにこれらを組み合わせた結合基で中断されていてもよく、R30およびR31は、水素原子、炭素原子数1〜8のアルキル基、炭素原子数6〜20のアリール基または炭素原子数7〜20のアリールアルキル基を表し、Z1およびZ2は、それぞれ独立に、直接結合、−O−、−S−、>CO、−CO−O−、−O−CO−、−SO2−、−SS−、−SO−または>NR33を表し、R32およびR33は、水素原子、置換基を有していてもよい炭素原子数1〜35の脂肪族炭化水素基、置換基を有していてもよい炭素原子数6〜35の芳香族炭化水素基または置換基を有していてもよい炭素原子数2〜35の複素環基を表す。なお、*は、*部分で、隣接する基と結合することを意味する。
本発明の硬化性組成物に係る感光性基を有する水溶性重合体(B)としては、ポリビニアルコール、シラノール基等で変性されたポリビニルアルコール誘導体、ポリビニルアルコールに(メタ)アクリレートまたは(メタ)アクリルアミド構造を導入したポリビニルアルコール誘導体、酸化澱粉、エーテル化・エステル化・グラフト化された変性澱粉、ゼラチン・カゼイン・カルボキシメチルセルロース等のセルロース誘導体、ポリビニルピロリドン、水溶性ポリエステル樹脂、水溶性ポリアクリル酸エステル樹脂、水溶性ポリカーボネート樹脂、水溶性ポリ酢酸ビニル樹脂、水溶性スチレンアクリート樹脂、水溶性ビニルトルエンアクリレート樹脂、水溶性ポリウレタン樹脂、水溶性ポリアミド樹脂、水溶性尿素樹脂、水溶性ポリカプロラクトン樹脂、水溶性ポリスチレン樹脂、水溶性ポリ塩化ビニル樹脂、水溶性ポリアクリレート樹脂、水溶性ポリアクリロニトリル樹脂等の水溶性樹脂;スチレン・ブタジエン共重合体、アクリル酸エステル共重合体、ポリ酢酸ビニル、エチレン・酢酸ビニル共重合体等の水溶性重合体に、ビニル基、アリル基、スチリル基、シンナミル基、シンナモイル基、シンナミリデン基、シンナミリデンアセチル基、カルコン基、クマリン基、イソクマリン基、2,5−ジメトキシスチルベン基、マレイミド基、α−フェニルマレイミド基、2−ピロン基、アジド基、チミン基、キノン基、マレイミド基、ウラシル基、ピリミジン基、スチルバゾリウム基、スチリルピリジニウム基、スチリルキノリウム基、エポキシ基、オキセタン基、ビニルエーテル基、アリルエーテル基、アセチルアセトン構造またはβ−ジケトン構造等の感光性基を導入したもの;スチレン・ブタジエン共重合体、アクリル酸エステル共重合体、ポリ酢酸ビニル、エチレン・酢酸ビニル共重合体等の水溶性重合体に、ヒドロキシル基、カルボニル基、ホルミル基等を有する(メタ)アクリレートまたはヒドロキシル基を有する(メタ)アクリルアミドをグラフト化させたものが挙げられる。
本発明の硬化性組成物には、必要に応じて、ラジカル開始剤、増感剤、カップリング剤、架橋剤および溶媒を加えることもできる。
[表1]〜[表3]の配合により各成分を混合して、室温で1時間撹拌後、1μmフィルターでろ過し、各実施例および比較例の硬化性組成物を得た。なお、実施例および比較例では部は質量部を意味する。また、[表1]〜[表3]中のPV−1〜PV−4およびPV’−1〜PV’−3の配合量は、溶媒以外の成分の比率(質量%)である。さらに、PV’−1〜PV’−3は、以下の手順で調整した。
まず、イオン交換水90.0gを室温で撹拌しているところに、下記の比較水溶性重合体(B’−1、B’−2、B’−3)10.0gを徐々に添加した。室温で1時間撹拌した後に、内温が85から90℃になるまで加熱し、その温度で2時間撹拌を継続した。溶解を確認した後、室温まで冷却した。調製した水溶液は1μmフィルターでろ過した。
B’−1:日本合成化学工業製 ゴーセノールNL−05
B’−2:日本合成化学工業製 G−Polymer OKS−1083
B’−3:日本合成化学工業製 ゴーセネックス Z−200
実施例1〜14および比較例1〜6で得られた硬化性組成物の水溶液の状態を透明なサンプル瓶に入れ、目視で確認を行なった。判定基準は下記の通りである。
○:透明均一
△:僅かに白濁
×:白濁、分離あるいは析出物確認
この評価が○、△のものは、保存安定性が高く、硬化性組成物として好ましく用いることができ、評価が○のものは特に好ましい。評価が×のものは、保存安定性が低く、硬化性組成物としては好ましくない。
実施例1〜14および比較例1〜6で得られた硬化性組成物をガラス基板上にスピンコーターを用いて塗布した後、90℃のホットプレートで5分間プリベークを行なった。このときの膜の状態を確認した。尚、膜厚は触針法で5.0〜5.5μmとなるようスピンコートの条件を調整した。判定基準は下記の通りである。
○:透明均一
△:僅かに白濁
×:白濁、あるいは析出物確認
この評価が○、△のものは、光学材料に用いる硬化性組成物として好ましく用いることができ、評価が○のものは特に好ましい。評価が×のものは、光学材料に用いる硬化性組成物としては好ましくない。
a)露光
プリベークをおこなった基板に対し、フォトマスク(LINE/SPACE=100μm/100μm)を介し、高圧水銀ランプを用い、各塗膜に365nmの波長を含む光を1000mJ/cm2で照射した。
a)で露光を行なった膜を23℃のイオン交換水に1分間浸漬した後、エアーガンで付着した水を除去し、基板を120℃のオーブン内で10分乾燥させた。現像、乾燥後のパターンをレーザー顕微鏡で確認し、フォトリソグラフィー性評価とした。判定基準は下記の通りである。
○:パターンが100±5μm以内のもの
△:100±10μm以内のもの
×:100±10μm超あるいはパターンが無くなっているもの
この評価が○、△のものは、フォトリソグラフィー性が必要な硬化性組成物として好ましく用いることができ、評価が○のものは特に好ましい。評価が×のものは、フォトリソグラフィー性が必要な硬化性組成物としては好ましくない。
上記塗布性試験において得られた塗膜上に、下記液晶化合物No.1〜No.11よりなる液晶組成物を接し、60℃で24間後、液晶組成物を取り出すことにより樹脂溶出性試験を行った。取り出した液晶組成物について樹脂溶出性試験前後でのVHR(電圧保持率)を比較し、VHRの低下率を求め、下記基準により評価を行った。評価は、液晶組成物を液晶評価用TNセル(セル厚5μm、電極面積8mm×8mm配向膜JALS2096)に注入し、VHRをVHR−1A(東陽テクニカ製)を用い測定した。(測定条件:パルス電圧幅60μs、フレーム周期1.0s、波高±5V、測定温度25℃)
○:VHRの低下率が99%超
△:VHRの低下率が97〜99%
×:VHRの低下率が97%未満
この評価が○、△のものは、液晶への樹脂溶出が低いことから、樹脂溶出性に優れた硬化性組成物として好ましく用いることができ、評価が○のものは特に好ましい。評価が×のものは、液晶への樹脂溶出が高いことから好ましくない。
A−2:新中村化学工業社製 NKエステル A−GLY−20E(水溶性多官能アクリレート)
A−3:新中村化学工業社製 NKエコノマー A−PG5054E(水溶性多官能アクリレート)
A−4:新中村化学工業社製 NKエステル A−BPE−30(水溶性多官能アクリレート)
A−5:富士フイルム社製 FFM−2(水溶性多官能アクリルアミド)
A−6:新中村化学工業社製 NKエステル ATM−35E(水溶性多官能アクリレート)
A’−1:新中村化学工業社製 NKエステル A−400(非水溶性多官能アクリレート)
A’−2:新中村化学工業社製 NKエステル A−BPE−4(非水溶性多官能アクリレート)
A’−3:KJケミカルズ社製 ヒドロキシエチルアクリルアミド(HEAA)(水溶性単官能アクリルアミド)
PV−1:ゴーセノールGL−05にN−メチロールアクリルアミドを作用させて固形分を10質量%に調整した水溶液
PV−2:G−Polymer OKS−1083にN−メチロールアクリルアミドを作用させて固形分を10質量%に調整した水溶液
PV−3:G−Polymer OKS−1083にホルミルスチリルピリジニウムを作用させて固形分を10質量%に調整した水溶液
PV−4:ゴーセノールGL−05にホルミルスチリルピリジニウムを作用させて固形分を10質量%に調整した水溶液
C−1:
C−2:
C−3:
C−4:
C−5:BASF社製 IRGACURE907
C−6:BASF社製 IRGACURE2959
C−7:
C−8:
C−9:
Claims (10)
- 水溶性多官能(メタ)アクリレートおよび水溶性多官能(メタ)アクリルアミドからなる群から選ばれる少なくとも1種(A)と、感光性基を有する水溶性重合体(B)と、を含有することを特徴とする硬化性組成物。
- 前記一般式(III)および(IV)において、Qが、ビニル基、アリル基、スチリル基、シンナミル基、シンナモイル基、シンナミリデン基、シンナミリデンアセチル基、カルコン基、クマリン基、イソクマリン基、2,5−ジメトキシスチルベン基、マレイミド基、α−フェニルマレイミド基、2−ピロン基、アジド基、チミン基、キノン基、マレイミド基、ウラシル基、ピリミジン基、スチルバゾリウム基、スチリルピリジニウム基、スチリルキノリウム基、エポキシ基、オキセタン基、ビニルエーテル基、アリルエーテル基、アセチルアセトン構造またはβ−ジケトン構造である請求項4記載の硬化性組成物。
- 前記感光性基を有する水溶性重合体(B)が、ポリビニルアルコールに(メタ)アクリレートまたは(メタ)アクリルアミド構造を導入したポリビニルアルコール誘導体である請求項1または2記載の硬化性組成物。
- さらに、ラジカル開始剤を含有する請求項1〜7のうちいずれか一項記載の硬化性組成物。
- 請求項1〜8のうちいずれか一項記載の硬化性組成物が硬化されてなることを特徴とする硬化物。
- 請求項1〜8のうちいずれか一項記載の硬化性組成物を、活性エネルギー線により硬化させることを特徴とする硬化方法。
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