JP7059384B2 - ジブチルフルオレニル誘導体及びその光開始剤としての使用 - Google Patents
ジブチルフルオレニル誘導体及びその光開始剤としての使用 Download PDFInfo
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- JP7059384B2 JP7059384B2 JP2020545844A JP2020545844A JP7059384B2 JP 7059384 B2 JP7059384 B2 JP 7059384B2 JP 2020545844 A JP2020545844 A JP 2020545844A JP 2020545844 A JP2020545844 A JP 2020545844A JP 7059384 B2 JP7059384 B2 JP 7059384B2
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- Japan
- Prior art keywords
- photocurable composition
- manufacture
- photoinitiator
- resists
- dibutylfluorenyl
- Prior art date
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- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 claims description 4
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- -1 9,9-dibutylfluorenyl Chemical group 0.000 description 31
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
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- 150000003926 acrylamides Chemical class 0.000 description 2
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- 239000007864 aqueous solution Substances 0.000 description 2
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- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
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- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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- 238000004383 yellowing Methods 0.000 description 2
- PDLPMGPHYARAFP-UHFFFAOYSA-N (3-hydroxy-2-phenylphenyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C=1C(O)=CC=CC=1C(=O)C1=CC=CC=C1 PDLPMGPHYARAFP-UHFFFAOYSA-N 0.000 description 1
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- OQPNDCHKFIHPBY-UHFFFAOYSA-N 1,2-dichloro-2-methylpropane Chemical compound CC(C)(Cl)CCl OQPNDCHKFIHPBY-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
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- ZYZWCJWINLGQRL-UHFFFAOYSA-N 4-phenylcyclohexa-2,4-diene-1,1-diol Chemical group C1=CC(O)(O)CC=C1C1=CC=CC=C1 ZYZWCJWINLGQRL-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
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- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
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- 125000001931 aliphatic group Chemical group 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
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- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- 238000003988 headspace gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
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- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
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- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N omega-Hydroxydodecanoic acid Natural products OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
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- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/108—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
- C07C2/861—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only halogen as hetero-atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
-
- 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
- C08F222/00—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 a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
-
- 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
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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
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
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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
- C08F222/00—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 a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/103—Esters of polyhydric alcohols or polyhydric phenols of trialcohols, e.g. trimethylolpropane tri(meth)acrylate
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Description
エポキシアクリレート 約35%
反応性アミン共開始剤 約7%
トリメチロールプロパントリアクリレート 約55%
光開始剤化合物 約3%
を含む。
2-メチル-1-(2-(9,9-ジブチルフルオレニル))-2-(N-モルホリニル)-1-アセトンの合成
2-メチル-1-(2-(9,9-ジブチルフルオレニル))-2-(N-モルホリニル)-1-アセトンの合成経路は以下の通りである。
100mLの三口フラスコに12mmol(1.99g)のフルオレン、0.5mmol(0.16g)の相間移動触媒である臭化テトラ-n-ブチルアンモニウム、4.5mLの50%水酸化ナトリウム水溶液、29mmol(3.1mL)のn-ブロモブタン及び50mLのブタノンを入れた。3-4時間加熱還流し、反応終了まで薄層クロマトグラフィーにより反応を追跡した。溶媒であるブタノンを留去した後、塩化メチレンで抽出した(10mLx3回)。有機層を合わせた後、無水硫酸ナトリウムで乾燥させ、回転蒸発により溶媒を除去した後、目標生成物を得た。
250mLの三口フラスコに0.01mol(1.0mL)のイソブチリルクロリド、0.01 mol(2.78g)の9,9-ジブチルフルオレン及び40mLの塩化メチレンを入れた。磁気撹拌により均一に混合し、氷浴で冷却した。磁気撹拌しながら10℃以下で合計0.012mol(1.58g)の三塩化アルミニウムを2バッチで添加した後、室温に昇温し、3時間撹拌し、さらに40℃に昇温し、引き続き1時間撹拌した。撹拌しながら、反応混合物を100gの氷水にゆっくりと入れた。静置して二層に分けた後、水層を分離して除去し、有機層を氷水で洗浄(30mLx3回)した後、基本的に中性になった。乾燥させた後、塩化メチレンを除去して目標生成物を得た。
250 mL的三口フラスコに50mLの塩化メチレン、15 mLの80%硫酸、0.20molの過酸化水素及び0.10mol(34.85g)の2-(2-メチルプロピオニル)-9,9-ジブチルフルオレンを入れた。温度を25-30℃に制御し、1.0-1.5時間内に0.07mol(3.6mL)の臭素を滴下した。臭素滴下終了の20分間後、HPLCにより2-(2-メチルプロピオニル)-9,9-ジブチルフルオレンが完全に反応したことが確認された。冷却下で撹拌しながら30%の水酸化ナトリウム溶液を滴下し、上記反応混合物をpHが中性になるまで中和した後、静置して二層に分けた。水層を塩化メチレンで抽出(20mLx2回)した。有機層を合わせ、乾燥させ、回転蒸留により溶媒である塩化メチレンを除去し、目標生成物を得た。
250mLの三口フラスコに50mLの無水メタノール及び0.12mol(2.76g)の金属ナトリウムを入れ、ナトリウムメトキシドのメタノール溶液を調製した。温度を25-30℃に制御し、1.5-2.0時間内に0.10mol(4.27g)の2-(2-ブロモ-2-メチルプロピオニル)-9,9-ジブチルフルオレンを3バッチで添加した。添加終了後、引き続き1時間反応させた。HPLCにより2-(2-ブロモ-2-メチルプロピオニル)-9,9-ジブチルフルオレンが完全に反応したことが確認された後、60℃で回転蒸留によりを溶媒であるメタノールを除去し、冷却し、白色固体を得た。生成物を生成せず、そのまま次の反応に供した。
方法1:ステップ(4)の反応生成物2-メチル-1-メトキシ[2-(9,9-ジブチルフルオレニル)]酸化プロピレン3.67g(10.0mmol)を取り、100mL反応フラスコに入れ、モルホリン2.61g(30.0mmol)を添加し、120-130℃で20時間撹拌しながら反応させた。薄層クロマトグラフィーにより反応を追跡した後、過剰なモルホリンなどの溶媒を減圧留去し、次に、カラムクロマトグラフィー(移動相:石油エーテル-酢酸エチル)により分離して精製し、目標化合物2-メチル-1-(2-(9,9-ジブチルフルオレニル))-2-(N-モルホリニル)-1-アセトン3.63gを得た。収率は83.7%出会った。
1HNMR(400MHz,CDCl3)δ:8.74(d,J=0.8Hz,1H),8.48(dd,J1=8.0Hz,J2=0.8Hz,1H),7.78-7.73(m,2H),7.39-7.37(m,3H),3.74(t,J=4.8Hz,4H),2.66-2.64(m,4H),2.05-2.00(m,4H),1.59(s,6H),1.13-1.06(m,4H),0.69-0.60(m,10H);13CNMR(100MHz,CDCl3)δ:202.9,151.9,149.8,145.2,140.0,129.6,128.1,127.0,125.0,123.0,120.6,119.0,76.9,67.4,55.0,47.1,40.1,26.0,23.0,20.4,13.8.ESRMsm/z=434.3[M+H]+。
光硬化ワニス製品の調製
以下の処方に従って光硬化ワニス製品を調製した。
具体的な処方は以下の通りである。
成分 組成物の合計重量の重量%
エポキシアクリレート 35%
活性アミンP115 7%
トリメチロールプロパントリアクリレート 55%
光開始剤 3%
上記処方に従って、2-メチル-1-(2-(9,9-ジブチルフルオレニル))-2-(N-モルホリニル)-1-アセトンを光開始剤として本発明の製品を製造した。
2-メチル-1-[4-メチルチオフェニル]-2-モルホリニル-1-アセトンを光開始剤で調製した対照製品1、
2-メチル-1-(4-ビフェニル)-2-モルホリニル-1-アセトンを光開始剤で調製した対照製品2、
を含む。
硬化効果試験
実施例2で調製したワニス製品を印刷適性試験機により白紙に約15μmの厚さで塗布し、電力が50W/CMの調整可能なフィルタ付きのUVランプを用いて360-420の波長範囲下、100m/分間の速度で硬化し、良好な表面が形成されかつ完全に硬化するために必要なランプ下での通過回数を記録した。結果を表1に示す。
VOC放出分析
ヘッドスペースガスクロマトグラフィーにより実施例3で本発明の光開始剤により調製した硬化膜におけるVOC放出量を測定した。
溶解度、黄変及びにおい分析
固体の光開始剤(本発明の化合物2-メチル-1-(2-(9,9-ジブチルフルオレニル))-2-(N-モルホリニル)-1-アセトン、対照光開始剤2-メチル-1-[4-メチルチオフェニル]-2-モルホリニル-1-アセトン及び2-メチル-1-(4-ビフェニル)-2-モルホリニル-1-アセトン)
安定性分析
実施例2で調製したワニス製品を15μmワイヤーバーコータにより12×12cm板紙に塗布し、電力が80W/cmの中圧水銀アークランプを用いて20m/分間の速度で硬化した。板紙を10×10cmの大きさに切り出し、100mlの蒸留水、3%酢酸水溶液の2種類の模擬液に完全に浸漬し、密封した後40℃の条件下で10日間静置した。印刷物を取り出し、静置した後、そのままHPLCにより模擬液中の開始剤化合物の含有量を分析した。600cm2の印刷面積で1kgの食品を包むことで計算し、遷移率測定結果をg/Kg食品で示し、その結果を表4に示す。
Claims (3)
- 着色又は非着色のペイント、着色又は非着色のワニス、粉末塗料、印刷インキ、プリント基板、粘着剤、歯科用組成物、ゲル塗料、エレクトロニクス用フォトレジスト、メッキレジスト、液体膜及びドライ膜、ソルダーレジスト、表示用カラーフィルタ用のレジストの製造;
プラズマディスプレイパネル、エレクトロルミネセントディスプレイ、又はLCDの製造過程において構造を形成するためのレジストの製造;
LCDスペーサ、ホログラフィックデータストレージ、又は電気及び電子部品をパッケージする組成物の製造;
磁気記録材料、マイクロ機械部品、光学スイッチ、メッキマスク、エッチングマスク、色校正システム、グラスファイバーケーブル塗料、又はスクリーン印刷テンプレートの製造;
ステレオリソグラフィー技術による三次元オブジェクトの製造;
画像記録材料、ホログラフィック記録、マイクロエレクトロニクス回路、脱色材料、又はマイクロカプセルを用いる画像記録材料、
における、請求項1に記載の光硬化性組成物の使用。 - 請求項1に記載の光硬化性組成物を基材上に塗布し、波長が150-600nmの範囲の光で照射することを含む、光硬化性組成物の硬化方法。
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CN201711175135.1A CN108117616B (zh) | 2017-11-22 | 2017-11-22 | 二丁基芴基衍生物与其作为光引发剂的应用 |
PCT/CN2018/116999 WO2019101142A1 (zh) | 2017-11-22 | 2018-11-22 | 二丁基芴基衍生物与其作为光引发剂的应用 |
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JP6817503B1 (ja) * | 2019-05-29 | 2021-01-20 | 株式会社Dnpファインケミカル | カラーフィルタ用感光性着色樹脂組成物、硬化物、カラーフィルタ、及び表示装置 |
JPWO2021125132A1 (ja) * | 2019-12-20 | 2021-06-24 | ||
WO2022091711A1 (ja) * | 2020-10-27 | 2022-05-05 | 株式会社Dnpファインケミカル | 感光性着色樹脂組成物、硬化物、カラーフィルタ、及び表示装置 |
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US11560362B2 (en) | 2023-01-24 |
EP3715381A4 (en) | 2020-09-30 |
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CN108117616A (zh) | 2018-06-05 |
WO2019101142A1 (zh) | 2019-05-31 |
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