JP2022528234A - Habi類混合光開始剤のuvled光硬化への応用 - Google Patents
Habi類混合光開始剤のuvled光硬化への応用 Download PDFInfo
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- JP2022528234A JP2022528234A JP2021557999A JP2021557999A JP2022528234A JP 2022528234 A JP2022528234 A JP 2022528234A JP 2021557999 A JP2021557999 A JP 2021557999A JP 2021557999 A JP2021557999 A JP 2021557999A JP 2022528234 A JP2022528234 A JP 2022528234A
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- Prior art keywords
- meth
- habi
- compound
- bis
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- 238000000016 photochemical curing Methods 0.000 title claims abstract description 12
- GMIUUCWUOPOETN-UHFFFAOYSA-N 2,4,5-triphenyl-1-(2,4,5-triphenylimidazol-2-yl)imidazole Chemical compound C1=CC=CC=C1C1=NC(N2C(=C(N=C2C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C=CC=CC=2)(C=2C=CC=CC=2)N=C1C1=CC=CC=C1 GMIUUCWUOPOETN-UHFFFAOYSA-N 0.000 title claims 10
- 239000011342 resin composition Substances 0.000 claims abstract description 24
- 239000003999 initiator Substances 0.000 claims abstract description 21
- -1 bisimidazole compound Chemical class 0.000 claims description 93
- 150000001875 compounds Chemical class 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 239000000852 hydrogen donor Substances 0.000 claims description 17
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 15
- AZUHIVLOSAPWDM-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-1h-imidazole Chemical class C1=CNC(C=2NC=CN=2)=N1 AZUHIVLOSAPWDM-UHFFFAOYSA-N 0.000 claims description 14
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 7
- 230000008033 biological extinction Effects 0.000 claims description 6
- JTMBCYAUSCBSEY-UHFFFAOYSA-N 2-methyl-2-sulfanylpropanoic acid Chemical compound CC(C)(S)C(O)=O JTMBCYAUSCBSEY-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical group 0.000 claims description 5
- WQECNJBUYKDLGS-UHFFFAOYSA-N 2-(2-methyl-2-sulfanylpropanoyl)oxyethyl 2-methyl-2-sulfanylpropanoate Chemical compound CC(C)(S)C(=O)OCCOC(=O)C(C)(C)S WQECNJBUYKDLGS-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
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- TXJZAWRTHMZECY-UHFFFAOYSA-N 2-(3-sulfanylbutanoyloxy)ethyl 3-sulfanylbutanoate Chemical compound CC(S)CC(=O)OCCOC(=O)CC(C)S TXJZAWRTHMZECY-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
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- VTLHIRNKQSFSJS-UHFFFAOYSA-N [3-(3-sulfanylbutanoyloxy)-2,2-bis(3-sulfanylbutanoyloxymethyl)propyl] 3-sulfanylbutanoate Chemical compound CC(S)CC(=O)OCC(COC(=O)CC(C)S)(COC(=O)CC(C)S)COC(=O)CC(C)S VTLHIRNKQSFSJS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 28
- 239000001294 propane Substances 0.000 description 26
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- 239000000203 mixture Substances 0.000 description 20
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 12
- 238000005259 measurement Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 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 10
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000008878 coupling Effects 0.000 description 8
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- 238000000034 method Methods 0.000 description 8
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 8
- 150000003254 radicals Chemical group 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 235000019645 odor Nutrition 0.000 description 7
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 244000028419 Styrax benzoin Species 0.000 description 6
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- 238000011522 transarterial infusion chemotherapy Methods 0.000 description 6
- PMNLUUOXGOOLSP-UHFFFAOYSA-M 2-sulfanylpropanoate Chemical compound CC(S)C([O-])=O PMNLUUOXGOOLSP-UHFFFAOYSA-M 0.000 description 5
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- 229910019142 PO4 Inorganic materials 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
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- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 4
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- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
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- AGBVBBKNTPSNBH-UHFFFAOYSA-N cyclohexyl 2-[4-[4,6-bis(trichloromethyl)-1,3,5-triazin-2-yl]phenyl]sulfanylacetate Chemical compound ClC(Cl)(Cl)C1=NC(C(Cl)(Cl)Cl)=NC(C=2C=CC(SCC(=O)OC3CCCCC3)=CC=2)=N1 AGBVBBKNTPSNBH-UHFFFAOYSA-N 0.000 description 1
- 150000003946 cyclohexylamines Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
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- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical class CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- 125000005805 dimethoxy phenyl group Chemical group 0.000 description 1
- VLNBQUAHERCLKT-UHFFFAOYSA-N dimethylamino benzoate Chemical compound CN(C)OC(=O)C1=CC=CC=C1 VLNBQUAHERCLKT-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical class CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
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- MZRQZJOUYWKDNH-UHFFFAOYSA-N diphenylphosphoryl-(2,3,4-trimethylphenyl)methanone Chemical compound CC1=C(C)C(C)=CC=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MZRQZJOUYWKDNH-UHFFFAOYSA-N 0.000 description 1
- SUXCALIDMIIJCK-UHFFFAOYSA-L disodium;4-amino-3-[[4-[4-[(1-amino-4-sulfonatonaphthalen-2-yl)diazenyl]-3-methylphenyl]-2-methylphenyl]diazenyl]naphthalene-1-sulfonate Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(N=NC3=CC=C(C=C3C)C=3C=C(C(=CC=3)N=NC=3C(=C4C=CC=CC4=C(C=3)S([O-])(=O)=O)N)C)=CC(S([O-])(=O)=O)=C21 SUXCALIDMIIJCK-UHFFFAOYSA-L 0.000 description 1
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- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
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- NBNNDUZYMXBCOX-UHFFFAOYSA-N n-[4-[4-(4-methoxyphenoxy)-2,6-dimethylphenyl]-1,3-thiazol-2-yl]pyridine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1OC(C=C1C)=CC(C)=C1C1=CSC(NC(=O)C=2C=CN=CC=2)=N1 NBNNDUZYMXBCOX-UHFFFAOYSA-N 0.000 description 1
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- KSCKTBJJRVPGKM-UHFFFAOYSA-N octan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-] KSCKTBJJRVPGKM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- MLVYOYVMOZFHIU-UHFFFAOYSA-M sodium;4-[(4-anilinophenyl)diazenyl]benzenesulfonate Chemical compound [Na+].C1=CC(S(=O)(=O)[O-])=CC=C1N=NC(C=C1)=CC=C1NC1=CC=CC=C1 MLVYOYVMOZFHIU-UHFFFAOYSA-M 0.000 description 1
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- 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
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- 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
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
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- ROVRRJSRRSGUOL-UHFFFAOYSA-N victoria blue bo Chemical compound [Cl-].C12=CC=CC=C2C(NCC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)=C1C=CC(=[N+](CC)CC)C=C1 ROVRRJSRRSGUOL-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
-
- 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
-
- 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
-
- 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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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Polymerisation Methods In General (AREA)
- Materials For Photolithography (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
Description
前記HABI類混合光開始剤は、一般式(I)で示される構造を有し、2-1’、2-3’、2’-1及び2’-3の4種類の結合部位のビスイミダゾール化合物を含有し、かつ、HABI類混合光開始剤におけるこの4種類の結合部位のビスイミダゾール化合物の合計含有量(質量%)が92%以上である。
かつ、その中、2-位又は2’-位のアリール基上の少なくとも1つのオルト位置換基が電子吸引性置換基であり、4-位のアリール基または4’-位のアリール基または5-位のアリール基または5’-位のアリール基上の少なくとも1つの置換基に電子供与性置換基がある。
(c)水素供与体 0.01~15重量部
前記水素供与体と一般式(I)で示されるHABI類混合光開始剤との重量比が1:20~1:1である。
本発明のUVLED光硬化への応用において、HABI類混合光開始剤は、HABI類混合光開始剤と他の成分とからなる感光性樹脂組成物として使用される。
本発明のHABI類混合光開始剤は、一般式(I)で示される構造を有し、その中、2-1’、2-3’、2’-1及び2’-3の4種類の結合部位のビスイミダゾール化合物を含有し、かつ、混合光開始剤におけるこの4種類の結合部位のビスイミダゾール化合物の合計含有量(質量%)が92%以上である。
エチレン性不飽和二重結合を有する化合物は、感光性樹脂組成物の成膜を促進することができる。
本発明の感光性樹脂組成物は水素供与体をさらに含む。ビスイミダゾール類化合物は、光を照射した後に解離し、生成したモノイミダゾールラジカル基が体積が大きく、立体障害により活性が低くなり、単独でモノマーの重合を発生させにくく、しかし、水素供与体と組み合わせて使用すれば、モノイミダゾールラジカル基が水素供与体上の活性水素を奪いやすくなり、新しいリビングラジカル基を生じ、さらにモノマーの重合を発生させる。
任意選択として、本発明の感光性樹脂組成物は、協同/相乗効果により感光性樹脂組成物の光感度を柔軟に調整するために他の光開始剤及び/又は増感剤をさらに含んでもよい。
上記の各成分に加えて、任意選択として、本発明の感光性樹脂組成物には、さらに必要に応じてその他の助剤を適量で含有してもよい。助剤は、例えば、有機溶剤、染料、顔料、光発色剤、充填剤、可塑剤、安定剤、塗布助剤、剥離促進剤等のうちの少なくとも1種を添加してもよい。
本発明に記載の応用において、LED光源の波長が355~420nm範囲内にあり、365nm、385nm、395nm、405nmなどであってもよい。
1.1 HABI類混合光開始剤A1の製造
窒素ガスの保護下で、1Lの4つ口フラスコに、31.8gの2-(o-クロロフェニル)-4,5-ジフェニル-イミダゾール(INC)、51.3gの2,5-ビス(o-クロロフェニル)-4-(4,5-ジメトキシフェニル)-イミダゾール(TAI)、106gの30%液状水酸化ナトリウム、4.0gのテトラブチルアンモニウムブロマイドおよび300gのトルエンを投入し、加熱しながら撹拌し、60~65℃で130gの次亜塩素酸ナトリウム(濃度が11%)を滴下し、滴下終了後、温度を維持しながら反応させ、サンプルを取ってHPLCによりインプロセス制御を行い、INCもTAIも1%未満となると、反応の完全が示され、温度維持を終了する。
BCIM2: 2,2’-ビス(o-クロロフェニル)-4,4’,5,5’-テトラフェニル-2’,3-ジイミダゾール。
同様に、分離して得られた純粋TCTMに対して分析を行い、主構造が4つの結合部位の製品に対して、LCMSにより構造確認を行った。質量分析装置に付いたソフトウェアにより849と850という分子のフラグメントピークを取得し、製品の分子量が848であり、T+1およびT+2に該当し、この4つの生成物は構造が類似し、分子量が同じであることが証明された。TCTMを合成するモノイミダゾールTAIは、非対称のモノイミダゾールであるので、TAIは、下記のように、2種類の立体配置、つまりTAI1及びTAI2がある。
TCTM2: 2,2’,4,5’-テトラ(o-クロロフェニル)-4’,5-ビス(3,4-ジメトキシフェニル)-1,2’-ジイミダゾール
TCTM3: 2,2’,5,5’-テトラ(o-クロロフェニル)-4,4’-ビス(3,4-ジメトキシフェニル)-1,2’-ジイミダゾール
TCTM4: 2,2’,4,5’-テトラ(o-クロロフェニル)-4’,5-ビス(3,4-ジメトキシフェニル)-2’,3-ジイミダゾール。
TCDM2: 2,2’,5-トリス-(o-クロロフェニル)-4-(3,4-ジメトキシフェニル)-4’,5’-ジフェニル-2’,3-ジイミダゾール
TCDM3: 2,2’,5-トリス-(o-クロロフェニル)-4-(3,4-ジメトキシフェニル)-4’,5’-ジフェニル-2,3’-ジイミダゾール
TCDM4: 2,2’,5-トリス-(o-クロロフェニル)-4-(3,4-ジメトキシフェニル)-4’,5’-ジフェニル-1’,2-ジイミダゾール。
A1の製造方法を参照して、それぞれA2-A8を製造し、各製品の情況を下記の表1に示す。
2.1 測定すべきサンプルの製造
Ebecryl605及びEbecryl350(CytecIndustriesInc.社製)を99.5:0.5の重量比で均一に混合し、さらに3重量部の光開始剤および1重量部の水素供与体EsacureEDB(Lamberti S.p.A., ITから購入)を添加し、測定すべき組成物を作製した。
測定すべき組成物サンプルをFT-IR(FT-IR430-Jasco)のサンプル保存室に放置し、LED光源(365、385、395又は405nm)下で露光させ、LED光源をサンプル65mmの距離に位置させて30°の角度をなすようにした。
測定結果を下記の表に示し、3S内のピーク面積の低下程度(%)で表す。
3.1 測定すべきサンプルの製造
A1、A2、A3、A11、A12、A13を例として、下記の配合によりサンプルを作製し、成膜性能を評価する。
光開始剤 5重量部
N-PG(水素供与体) 1重量部。
測定すべき組成物サンプルを遮光状態で均一に撹拌し、サンプルを取ってPET基板上に放置し、ワイヤーバー25#で塗布し、厚さ25μmの塗膜を形成し、その後、LED光源(照射波長が385nm、露光量が240mj/cm2)を用いて塗膜を照射して硬化させた。
具体的な測定結果を表4に示す。
Claims (15)
- 使用する感光性樹脂組成物は、下記(a)~(c)の成分を含むことを特徴とするHABI類混合光開始剤のUVLED光硬化への応用。
(a)HABI類混合光開始剤 0.1~20重量部
前記HABI類混合光開始剤は、一般式(I)で示される構造を有し、2-1’、2-3’、2’-1及び2’-3の4種類の結合部位のビスイミダゾール化合物を含有し、かつ、HABI類混合光開始剤におけるこの4種類の結合部位のビスイミダゾール化合物の合計含有量(質量%)が92%以上である。
[式中、Ar1、Ar2、Ar3、Ar4、Ar5、Ar6は、同じであっても異なっていてもよく、それぞれ独立にして置換もしくは無置換のアリール基を表す。]
かつ、その中、2-位又は2’-位のアリール基上の少なくとも1つのオルト位置換基が電子吸引性置換基であり、4-位のアリール基または4’-位のアリール基または5-位のアリール基または5’-位のアリール基上の少なくとも1つの置換基に電子供与性置換基がある。
前記HABI類混合光開始剤は、355~420nmにおけるモル吸光係数が6000超え13000未満である。
(b)少なくとも1種の、エチレン性不飽和二重結合を有する化合物 25~99重量部
(c)水素供与体 0.01~15重量部
前記水素供与体と一般式(I)で示されるHABI類混合光開始剤との重量比が1:20~1:1である。 - 一般式(I)中、前記アリール基はフェニル基であることを特徴とする請求項1に記載の応用。
- 一般式(I)中、アリール基上の電子吸引性置換基は、ハロゲン元素、ニトロ基、シアノ基、アミノ基から選択され、アリール基上の電子供与性置換基は、メトキシ基、C3~C10の分岐アルキル基またはアルケニル基から選択されることを特徴とする請求項1に記載の応用。
- 一般式(I)中、Ar1、Ar2、Ar3、Ar4、Ar5、Ar6のうちの少なくとも1つは、ハロゲン元素置換基を含有するアリール基であり、好ましくは、ハロゲン元素置換基が塩素であることを特徴とする請求項1又は2に記載の応用。
- HABI類混合光開始剤において、一般式(I)で示される構造を満足する2-1’、2-3’、2’-1及び2’-3の4種類の結合部位のビスイミダゾール化合物の合計含有量(質量%)が95%以上であることを特徴とする請求項1に記載の応用。
- 前記HABI類混合光開始剤は、一般式(I)で示される構造を満足する2-1’、2-3’、2’-1及び2’-3の4種類の結合部位のビスイミダゾール化合物からなることを特徴とする請求項1又は5に記載の応用。
- 前記したエチレン性不飽和二重結合を有する化合物は、α,β-不飽和カルボン酸と多価アルコールとの反応で得られた化合物;ビスフェノールA類(メタ)アクリレート化合物;α,β-不飽和カルボン酸とグリシジル基含有化合物との反応で得られた化合物;分子内にウレタン結合を有する(メタ)アクリレート化合物;ノニルフェノキシポリエチレンオキシアクリレート;γ-クロロ-β-ヒドロキシプロピル-β’-(メタ)アクリロイルオキシエチル-o-フタレート;β-ヒドロキシエチル-β’-(メタ)アクリロイルオキシエチル-o-フタレート;β-ヒドロキシプロピル-β’-(メタ)アクリロイルオキシエチル-o-フタレート;フタル酸系化合物;アルキル(メタ)アクリレートから選択されることを特徴とする請求項1に記載の応用。
- 前記したエチレン性不飽和二重結合を有する化合物は、ビスフェノールA類(メタ)アクリレート化合物および分子内にウレタン結合を有する(メタ)アクリレート化合物から選択されることを特徴とする請求項1又は7に記載の応用。
- 前記水素供与体は、アミン又はアミン変性化合物、チオール類化合物であり、それらはヘテロ原子に隣接する炭素と連結する有効水素を有することを特徴とする請求項1に記載の応用。
- 前記アミン又はアミン変性化合物は、EsacureA198、EsacureEDB、2-エチルヘキシル-4-ジメチルアミノベンゾエートおよびN-フェニルグリシンから選択される少なくとも1種であることを特徴とする請求項9に記載の応用。
- 前記チオール類化合物は、エチレングリコールビス(3-メルカプトブチレート)、1,2-プロピレングリコール(3-メルカプトブチレート)、エチレングリコールビス(2-メルカプトイソブチレート)、1,2-プロピレングリコールビス(2-メルカプトイソブチレート)、ペンタエリスリトールテトラキス(3-メルカプトブチレート)から選択される少なくとも1種であることを特徴とする請求項9に記載の応用。
- 前記水素供与体と一般式(I)で示されるHABI類混合光開始剤との重量比が1:20~1:3であることを特徴とする請求項1に記載の応用。
- 前記感光性樹脂組成物には、他の光開始剤及び/又は増感剤をさらに含有してもよいことを特徴とする請求項1に記載の応用。
- 前記応用において、UVLED光源の波長が355~420nmの範囲内にあり、365nm、385nm、395nm、405nmを含むことを特徴とする請求項1に記載の応用。
- 前記感光性樹脂組成物は、インク及び塗料組成物として使用されることを特徴とする請求項1に記載の応用。
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