JP5566378B2 - オキシムエステル光開始剤 - Google Patents
オキシムエステル光開始剤 Download PDFInfo
- Publication number
- JP5566378B2 JP5566378B2 JP2011512067A JP2011512067A JP5566378B2 JP 5566378 B2 JP5566378 B2 JP 5566378B2 JP 2011512067 A JP2011512067 A JP 2011512067A JP 2011512067 A JP2011512067 A JP 2011512067A JP 5566378 B2 JP5566378 B2 JP 5566378B2
- Authority
- JP
- Japan
- Prior art keywords
- meth
- alkyl
- phenyl
- acrylate
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- -1 Oxime ester Chemical class 0.000 title claims description 273
- 239000000203 mixture Substances 0.000 claims description 181
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 130
- 125000000217 alkyl group Chemical group 0.000 claims description 130
- 150000001875 compounds Chemical class 0.000 claims description 129
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 102
- 239000000049 pigment Substances 0.000 claims description 83
- 239000000758 substrate Substances 0.000 claims description 75
- 238000000034 method Methods 0.000 claims description 63
- 229910052736 halogen Inorganic materials 0.000 claims description 58
- 150000002367 halogens Chemical group 0.000 claims description 57
- 229920000642 polymer Polymers 0.000 claims description 56
- 238000004519 manufacturing process Methods 0.000 claims description 54
- 229920005989 resin Polymers 0.000 claims description 46
- 239000011347 resin Substances 0.000 claims description 46
- 239000000463 material Substances 0.000 claims description 45
- 239000000178 monomer Substances 0.000 claims description 43
- 238000000576 coating method Methods 0.000 claims description 33
- 239000011159 matrix material Substances 0.000 claims description 33
- 229910052740 iodine Inorganic materials 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 125000001624 naphthyl group Chemical group 0.000 claims description 24
- 125000006850 spacer group Chemical group 0.000 claims description 24
- 239000011230 binding agent Substances 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 239000003973 paint Substances 0.000 claims description 21
- 239000000654 additive Substances 0.000 claims description 19
- 125000001589 carboacyl group Chemical group 0.000 claims description 19
- 239000000843 powder Substances 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- 230000003287 optical effect Effects 0.000 claims description 18
- 229920002120 photoresistant polymer Polymers 0.000 claims description 18
- 239000002270 dispersing agent Substances 0.000 claims description 17
- 238000007639 printing Methods 0.000 claims description 15
- 229920000647 polyepoxide Polymers 0.000 claims description 14
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 239000007795 chemical reaction product Substances 0.000 claims description 12
- 150000008065 acid anhydrides Chemical class 0.000 claims description 11
- 239000000976 ink Substances 0.000 claims description 10
- 150000007519 polyprotic acids Polymers 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 238000013500 data storage Methods 0.000 claims description 8
- 238000005530 etching Methods 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 7
- 230000000996 additive effect Effects 0.000 claims description 6
- 238000010894 electron beam technology Methods 0.000 claims description 6
- 239000003822 epoxy resin Substances 0.000 claims description 6
- 239000003365 glass fiber Substances 0.000 claims description 6
- 239000002491 polymer binding agent Substances 0.000 claims description 6
- 238000007650 screen-printing Methods 0.000 claims description 6
- 230000001070 adhesive effect Effects 0.000 claims description 5
- 238000003384 imaging method Methods 0.000 claims description 5
- 150000001266 acyl halides Chemical class 0.000 claims description 4
- 239000000853 adhesive Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 238000009713 electroplating Methods 0.000 claims description 4
- 229920000620 organic polymer Polymers 0.000 claims description 4
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 3
- 230000005670 electromagnetic radiation Effects 0.000 claims description 3
- 239000003094 microcapsule Substances 0.000 claims description 3
- 238000004377 microelectronic Methods 0.000 claims description 3
- 239000003504 photosensitizing agent Substances 0.000 claims description 3
- 238000007747 plating Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 230000001678 irradiating effect Effects 0.000 claims description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 2
- 238000005476 soldering Methods 0.000 claims description 2
- 239000002966 varnish Substances 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 86
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 72
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical group CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 58
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 58
- 229920001577 copolymer Polymers 0.000 description 58
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 43
- 229910052760 oxygen Inorganic materials 0.000 description 36
- 239000010408 film Substances 0.000 description 35
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 32
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 32
- 239000004973 liquid crystal related substance Substances 0.000 description 31
- 239000002904 solvent Substances 0.000 description 28
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 26
- 229920005862 polyol Polymers 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 25
- 239000000047 product Substances 0.000 description 22
- 239000002253 acid Substances 0.000 description 21
- 239000011248 coating agent Substances 0.000 description 21
- 230000005855 radiation Effects 0.000 description 21
- 239000011342 resin composition Substances 0.000 description 21
- 125000004432 carbon atom Chemical group C* 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
- 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 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 239000011521 glass Substances 0.000 description 18
- 150000003077 polyols Chemical class 0.000 description 18
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 17
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 229910052717 sulfur Inorganic materials 0.000 description 17
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 16
- 210000004027 cell Anatomy 0.000 description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 16
- 125000001424 substituent group Chemical group 0.000 description 16
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 14
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 14
- 239000006185 dispersion Substances 0.000 description 14
- 238000010438 heat treatment Methods 0.000 description 14
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- 229920000728 polyester Polymers 0.000 description 14
- 239000000600 sorbitol Substances 0.000 description 14
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 13
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 13
- 239000000975 dye Substances 0.000 description 13
- 150000002148 esters Chemical class 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 12
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 12
- 229920001223 polyethylene glycol Polymers 0.000 description 12
- 150000003254 radicals Chemical class 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 11
- 125000002947 alkylene group Chemical group 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 11
- 239000003086 colorant Substances 0.000 description 11
- 125000003700 epoxy group Chemical group 0.000 description 11
- 239000011976 maleic acid Substances 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 11
- 239000004814 polyurethane Substances 0.000 description 11
- 229920002635 polyurethane Polymers 0.000 description 11
- 230000035945 sensitivity Effects 0.000 description 11
- 239000004094 surface-active agent Substances 0.000 description 11
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 10
- 239000002202 Polyethylene glycol Substances 0.000 description 10
- 239000004642 Polyimide Substances 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 150000001735 carboxylic acids Chemical class 0.000 description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- 238000011161 development Methods 0.000 description 10
- 229920003986 novolac Polymers 0.000 description 10
- 150000002923 oximes Chemical class 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- 229920001721 polyimide Polymers 0.000 description 10
- 239000002243 precursor Substances 0.000 description 10
- 229920003002 synthetic resin Polymers 0.000 description 10
- 239000000057 synthetic resin Substances 0.000 description 10
- 229920001187 thermosetting polymer Polymers 0.000 description 10
- 229920002554 vinyl polymer Polymers 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000003513 alkali Substances 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 239000003999 initiator Substances 0.000 description 9
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 9
- 239000011241 protective layer Substances 0.000 description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 9
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 8
- 239000004952 Polyamide Substances 0.000 description 8
- 239000004793 Polystyrene Substances 0.000 description 8
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 8
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 238000001723 curing Methods 0.000 description 8
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 8
- 239000011229 interlayer Substances 0.000 description 8
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 8
- 238000000206 photolithography Methods 0.000 description 8
- 229920002647 polyamide Polymers 0.000 description 8
- 229920002223 polystyrene Polymers 0.000 description 8
- 229910000679 solder Inorganic materials 0.000 description 8
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 description 7
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 7
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 7
- 230000004888 barrier function Effects 0.000 description 7
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 150000002009 diols Chemical class 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 7
- 238000000465 moulding Methods 0.000 description 7
- 229920000768 polyamine Polymers 0.000 description 7
- 238000012545 processing Methods 0.000 description 7
- 125000001544 thienyl group Chemical group 0.000 description 7
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 6
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 6
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 238000003491 array Methods 0.000 description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 125000002843 carboxylic acid group Chemical group 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 6
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 6
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 6
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 6
- 229920000570 polyether Polymers 0.000 description 6
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 6
- 229920005992 thermoplastic resin Polymers 0.000 description 6
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 5
- 0 CCN*1=CCC1C Chemical compound CCN*1=CCC1C 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000012965 benzophenone Substances 0.000 description 5
- 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 description 5
- 239000007859 condensation product Substances 0.000 description 5
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 5
- 125000004430 oxygen atom Chemical group O* 0.000 description 5
- 239000000123 paper Substances 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000004065 semiconductor Substances 0.000 description 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 5
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 5
- 239000002023 wood Substances 0.000 description 5
- 239000001052 yellow pigment Substances 0.000 description 5
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 4
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- 125000000913 palmityl 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])C([H])([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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- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- 125000002958 pentadecyl 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])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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- ZPNJBTBYIHBSIG-UHFFFAOYSA-N phenyl-(2,2,6,6-tetramethylpiperidin-4-yl)methanone Chemical compound C1C(C)(C)NC(C)(C)CC1C(=O)C1=CC=CC=C1 ZPNJBTBYIHBSIG-UHFFFAOYSA-N 0.000 description 1
- 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
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
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- ZOGYOOUMDVKYLM-UHFFFAOYSA-N phosphane phosphorous acid Chemical compound P.OP(O)O ZOGYOOUMDVKYLM-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
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- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
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- 230000000886 photobiology Effects 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
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- 229920001603 poly (alkyl acrylates) Polymers 0.000 description 1
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- 229920005575 poly(amic acid) Polymers 0.000 description 1
- 229920003217 poly(methylsilsesquioxane) Polymers 0.000 description 1
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- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
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- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
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- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- GVVKBARIYRBZHC-UHFFFAOYSA-N prop-2-enyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCC=C GVVKBARIYRBZHC-UHFFFAOYSA-N 0.000 description 1
- CYFIHPJVHCCGTF-UHFFFAOYSA-N prop-2-enyl 2-hydroxypropanoate Chemical compound CC(O)C(=O)OCC=C CYFIHPJVHCCGTF-UHFFFAOYSA-N 0.000 description 1
- AXLMPTNTPOWPLT-UHFFFAOYSA-N prop-2-enyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC=C AXLMPTNTPOWPLT-UHFFFAOYSA-N 0.000 description 1
- HPCIWDZYMSZAEZ-UHFFFAOYSA-N prop-2-enyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC=C HPCIWDZYMSZAEZ-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000006233 propoxy propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
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- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 239000001057 purple pigment Substances 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- INCIMLINXXICKS-UHFFFAOYSA-M pyronin Y Chemical compound [Cl-].C1=CC(=[N+](C)C)C=C2OC3=CC(N(C)C)=CC=C3C=C21 INCIMLINXXICKS-UHFFFAOYSA-M 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
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- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
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- 150000003384 small molecules Chemical class 0.000 description 1
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
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- 235000010288 sodium nitrite Nutrition 0.000 description 1
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- AXMCIYLNKNGNOT-UHFFFAOYSA-M sodium;3-[[4-[(4-dimethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)-[4-[ethyl-[(3-sulfonatophenyl)methyl]amino]phenyl]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 AXMCIYLNKNGNOT-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- LJFWQNJLLOFIJK-UHFFFAOYSA-N solvent violet 13 Chemical compound C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O LJFWQNJLLOFIJK-UHFFFAOYSA-N 0.000 description 1
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- 239000008117 stearic acid Substances 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004079 stearyl 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])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])[H] 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 239000000725 suspension 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
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
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- 125000000101 thioether group Chemical group 0.000 description 1
- JADVWWSKYZXRGX-UHFFFAOYSA-M thioflavine T Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C1=[N+](C)C2=CC=C(C)C=C2S1 JADVWWSKYZXRGX-UHFFFAOYSA-M 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 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
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000004654 triazenes Chemical class 0.000 description 1
- KKFOMYPMTJLQGA-UHFFFAOYSA-N tribenzyl phosphite Chemical compound C=1C=CC=CC=1COP(OCC=1C=CC=CC=1)OCC1=CC=CC=C1 KKFOMYPMTJLQGA-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-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
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 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
- 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
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 239000011345 viscous material Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/62—Oximes having oxygen atoms of oxyimino groups esterified
- C07C251/64—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids
- C07C251/66—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids with the esterifying carboxyl groups bound to hydrogen atoms, to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
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Description
R1およびR’1は、互いに独立して、水素、C3−C8シクロアルキル、または非置換であるか、または1つ以上のハロゲン、フェニルおよび/またはCNによって置換されたC1−C12アルキルであり;あるいは
R1およびR’1は、C2−C5アルケニルであり;あるいは
R1およびR’1は、非置換であるか、または1つ以上のC1−C6アルキル、ハロゲン、CN、OR3、SR4および/またはNR5R6によって置換されたフェニルであり;あるいは
R1およびR’1は、C1−C8アルコキシ、ベンジルオキシ;あるいは非置換であるか、または1つ以上のC1−C6アルキルおよび/またはハロゲンによって置換されたフェノキシであり;
R2およびR’2は、互いに独立して水素;非置換C1−C20アルキル、または1つ以上のハロゲン、OR3、SR4、C1−C20ヘテロアリール、C8−C20フェノキシカルボニル、C1−C20ヘテロアリールオキシカルボニル、NR5R6、COOR3、CONR5R6、
R2およびR’2は、NR5R6、
1つ以上のOによって中断され、1つ以上のハロゲン、OR3、フェニルおよび/またはOR3、SR4および/またはNR5R6によって置換されたフェニルにより場合によって置換されたC2−C20アルキルであり;あるいは
R2およびR’2は、非置換であるか、または1つ以上のC1−C6アルキル、フェニル、ハロゲン、OR3、SR4および/またはNR5R6によって置換されたフェニルであり;あるいは
R2およびR’2は、C2−C20アルカノイル、または非置換であるか、または1つ以上のC1−C6アルキル、フェニル、OR3、SR4および/またはNR5R6によって置換されたベンゾイルであり;あるいは
R2およびR’2は、1つ以上のOによって中断され、かつ/または1つ以上のヒドロキシル基によって場合により置換されたC2−C12アルコキシカルボニルであり;あるいは
R2およびR’2は、非置換であるか、またはC1−C6アルキル、ハロゲン、フェニル、OR3、SR4および/またはNR5R6によって置換されたフェノキシカルボニルであり;あるいは
R2およびR’2は、CN、CONR5R6、NO2、S(O)m−C1−C6アルキル;C1−C12アルキルまたはSO2−C1−C6アルキルによって場合により置換されたS(O)m−フェニルであり;あるいはC1−C12アルキルによって場合により置換されたSO2O−フェニルであり;あるいは
ジフェニルホスフィノイルまたはジ−(C1−C4アルコキシ)−ホスフィノイルであり;あるいは
R2およびR’2は、
mは1または2であり;
Ar3は、それぞれがハロゲン、C1−C12アルキル、C3−C8シクロアルキル、ベンジルおよび/またはフェノキシカルボニルによって1回または複数回置換され;あるいはそれぞれがフェニルによって、または1つ以上のOR3、SR4および/またはNR5R6によって置換されたフェニルによって置換され;あるいはそれぞれが1つ以上のOによって場合により中断され、かつ/または1つ以上のヒドロキシル基によって場合により置換されたC 2 −C12アルコキシカルボニルによって置換され;あるいはそれぞれがOR3、SR4、SOR4、SO2R4および/またはNR5R6によって置換されたフェニル、ナフチルまたはクマリニルであり;
M2は、直接結合、シクロヘキシレンまたはC1−C10アルキレンまたはC1−C10アルキレン−X−であり、そのC1−C10アルキレンまたはC1−C10アルキレン−X−は、1つ以上のOによって場合により中断され、かつ/または1つ以上のハロゲン、OR3、フェニル、またはOR3、SR4および/またはNR5R6によって置換されたフェニルによって場合により置換されており;あるいはM2は、それぞれが非置換であるか、または1つ以上のC1−C6アルキル、フェニル、ハロゲン、OR3、SR4および/またはNR5R6によって置換されたフェニレン、ナフチレンまたはフェニレン−X−であり;あるいはM2は、C1−C10アルキレン−C(O)−X−、C1−C10アルキレン−X−C(O)−、フェニレン−C(O)−X−またはC1−C10アルキレン−フェニレン−X−であり;
M3は、直接結合、シクロヘキシレンまたはC1−C10アルキレンまたはC1−C10アルキレン−X−であり、そのC1−C10アルキレンまたはC1−C10アルキレン−X−は、1つ以上のOによって場合により中断され、かつ/または1つ以上のハロゲン、OR3、フェニル、またはOR3、SR4および/またはNR5R6によって置換されたフェニルによって場合により置換されており;あるいは
M3は、それぞれが非置換であるか、または1つ以上のC1−C6アルキル、フェニル、ハロゲン、OR3、SR4および/またはNR5R6によって置換されたフェニレン、ナフチレンまたはフェニレン−X−であり;あるいは
M3は、C1−C10アルキレン−C(O)−X−、C1−C10アルキレン−X−C(O)−、フェニレン−C(O)−X−、C1−C10アルキレン−フェニレン−X−またはフェニレン−(CO)−フェニレンであり;
Xは、O、SまたはNR5であり;
X1は、O、S、SOまたはSO2であり;
X2は、直接結合、O、COもしくはNR5によって場合により中断されたC1−C20アルキレンであり、中断されていない、または中断されたC1−C20アルキレンは、非置換であるか、または1つ以上のハロゲン、OR3、COOR3、NR5R6、C1−C20ヘテロアリール、C1−C20ヘテロアリール−(CO)O、C1−C20ヘテロアリール−S、CONR5R6、
R3は、水素、C1−C20アルキルまたはフェニル−C1−C3アルキルであり;あるいは
R3は、OH、SH、−CN、C3−C6アルケノキシ、OCH2CH2CN、OCH2CH2(CO)O(C1−C4アルキル)、O(CO)−(C1−C4アルキル)、O(CO)−フェニル、(CO)OHおよび/または(CO)O(C1−C4アルキル)によって置換されたC1−C20アルキルであり;あるいは
R3は、1つ以上のOによって中断されたC2−C20アルキルであり;あるいは
R3は、(CH2CH2O)n+1H、(CH2CH2O)n(CO)−(C1−C8アルキル)、C1−C8アルカノイル、C2−C12アルケニル、C3−C6アルケノイル、またはO、S、CO、NR5によって場合により中断されたC3−C20シクロアルキルであり;あるいは
R3は、非置換であるか、または1つ以上のC1−C6アルキル、ハロゲン、OHおよび/またはC1−C4アルコキシによって置換されたベンゾイルであり;あるいは
R3は、それぞれが非置換であるか、またはハロゲン、OH、C1−C12アルキル、C1−C12アルコキシ、CN、NO2、フェニル−C1−C3アルキルオキシ、フェノキシ、C1−C12アルキルスルファニル、フェニルスルファニル、N(C1−C12アルキル)2、ジフェニルアミノおよび/または
nは1〜20であり;
R4は、水素、C1−C20アルキル、C2−C12アルケニル、C3−C20シクロアルキル、フェニル−C1−C3アルキルであり、そのC1−C20アルキル、C2−C12アルケニル、C3−C20シクロアルキル、フェニル−C1−C3アルキルは、O、S、CO、NR5によって場合により中断されており;あるいは
R4は、OH、SH、CN、C3−C6アルケノキシ、OCH2CH2CN、OCH2CH2(CO)O(C1−C4アルキル)、O(CO)−(C1−C4アルキル)、O(CO)−フェニル、(CO)OHまたは(CO)O(C1−C4アルキル)によって置換されたC1−C8アルキルであり;あるいは
R4は、(CH2CH2O)n+1H、(CH2CH2O)n(CO)−(C1−C8アルキル)、C1−C8アルカノイル、C2−C12アルケニル、C3−C6アルケノイルであり;あるいは
R4は、非置換であるか、または1つ以上のC1−C6アルキル、ハロゲン、−OH、C1−C4アルコキシまたはC1−C4アルキルスルファニルによって置換されたベンゾイルであり;あるいは
R4は、それぞれが非置換であるか、またはハロゲン、C1−C12アルキル、C1−C12アルコキシ、CN、NO2、フェニル−C1−C3アルキルオキシ、フェノキシ、C1−C12アルキルスルファニル、フェニルスルファニル、N(C1−C12アルキル)2、ジフェニルアミノ、(CO)O(C1−C8アルキル)、(CO)−C1−C8アルキル、(CO)N(C1−C8アルキル)2または
R5およびR6は、互いに独立して、水素、C1−C20アルキル、C2−C4ヒドロキシアルキル、C2−C10アルコキシアルキル、C2−C5アルケニル、C3−C20シクロアルキル、フェニル−C1−C3アルキル、C1−C8アルカノイル、C3−C12アルケノイル、ベンゾイルであり;あるいは
R5およびR6は、それぞれが非置換であるか、またはC1−C12アルキル、ベンゾイルまたはC1−C12アルコキシによって置換されたフェニル、ナフチルまたはC1−C20ヘテロアリールであり;あるいは
R5およびR6は、それらが結合したN原子と一緒になって、O、SまたはNR3によって場合により中断された5または6員の飽和または不飽和環を形成し、その環は、非置換であるか、または1つ以上のC1−C20アルキル、C1−C20アルコキシ、=O、SR4、OR3もしくはNR17R18、(CO)R19、NO2、ハロゲン、C1−C4ハロアルキル、CN、フェニル、
R5およびR6は、それらが結合したN原子と一緒になって複素芳香族環系を形成し、その複素芳香族環系は、非置換であるか、または1つ以上のC1−C20アルキル、C1−C4ハロアルキル、C1−C20アルコキシ、=O、SR4、OR3、NR17R18、(CO)R19、
R''1は、R1について示されている意味の1つを有し;
R''2は、R2について示されている意味の1つを有し;
R7は、水素、C1−C20アルキル;ハロゲン、フェニル、OH、SH、CN、C3−C6アルケノキシ、OCH2CH2CN、OCH2CH2(CO)O(C1−C4アルキル)、O(CO)−(C1−C4アルキル)、O(CO)−フェニル、(CO)OHまたは(CO)O(C1−C4アルキル)によって置換されたC1−C8アルキルであり;あるいは
R7は、1つ以上のOによって中断されたC2−C12アルキルであり;あるいは
R7は、(CH2CH2O)n+1H、(CH2CH2O)n(CO)−(C1−C8アルキル)、C2−C12アルケニルまたはC3−C8シクロアルキルであり;あるいは
R7は、それぞれが1つ以上のC1−C20アルキル、ハロゲン、C1−C12ハロアルキル、CN、NO2、OR3、SR4、SOR4、SO2R4またはNR5R6によって場合により置換されたフェニル、ビフェニル、ナフチルまたはC1−C20ヘテロアリールであり、置換基OR3、SR4またはNR5R6は、フェニル、ビフェニル、ナフチルまたはC1−C20ヘテロアリール環の炭素原子の1つとR3、R4、R5および/またはR6基を介して5または6員環を場合により形成し;
R8およびR9ならびにR’8およびR’9は、互いに独立して、水素、1つ以上のハロゲン、フェニル、CN、OH、SH、C1−C4アルコキシ、(CO)OHまたは(CO)O(C1−C4アルキル)によって場合により置換されたC1−C12アルキルであり;あるいは
R8およびR9ならびにR’8およびR’9は、1つ以上のC1−C6アルキル、ハロゲン、CN、OR3、SR4またはNR5R6によって場合により置換されたフェニルであり;あるいは
R8およびR9ならびにR’8およびR’9は、ハロゲン、CN、OR3、SR4、SOR4、SO2R4またはNR5R6であり、置換基OR3、SR4またはNR5R6は、フェニルの炭素原子の1つと、または置換基R7またはM3のナフチレンもしくはフェニレン基の炭素原子の1つとR3、R4、R5および/またはR6基を介して5または6員環を場合により形成し;あるいは
R8およびR9ならびにR’8およびR’9は、ともに
R10、R11、R12およびR13は、互いに独立して、水素、1つ以上のハロゲン、フェニル、CN、OH、SH、C1−C4アルコキシ、(CO)OHまたは(CO)O(C1−C4アルキル)によって場合により置換されたC1−C12アルキルであり;あるいは
R10、R11、R12およびR13は、1つ以上のC1−C6アルキル、ハロゲン、CN、OR3、SR4またはNR5R6によって場合により置換されたフェニルであり;あるいは
R10、R11、R12およびR13は、ハロゲン、CN、OR3、SR4またはNR5R6であり;
R14およびR15は、互いに独立して、水素、1つ以上のハロゲン、フェニル、CN、OH、SH、C1−C4アルコキシ、(CO)OHまたは(CO)O(C1−C4アルキル)によって場合により置換されたC1−C12アルキルであり;あるいはR14およびR15は、1つ以上のC1−C6アルキル、ハロゲン、CN、OR3、SR4またはNR5R6によって場合により置換されたフェニルであり;
R17およびR18は、互いに独立して、水素、C1−C20アルキル、C1−C4ハロアルキル、C3−C10シクロアルキルまたはフェニルであり;あるいは
R17およびR18は、それらが結合したN原子と一緒になってO、SまたはNR24によって場合により中断された5または6員の飽和または不飽和環を形成し;あるいは
R17およびR18は、互いに独立して、NR17R18が結合したフェニルまたはナフチル環のC原子の1つに結合したC 2 −C 5 アルキレンまたはC2−C5アルケニレンであり、前記C2−C5アルキレンまたはC2−C5アルケニレンは、O、COまたはNR24によって場合により中断されており、そのC2−C5アルキレンまたはC2−C5アルケニレンに対してベンゼン環が場合により縮合されており;
R19は、水素、OH、C1−C20アルキル、C1−C4ハロアルキル、O、COもしくはNR24によって中断されたC2−C20アルキル、O、S、COもしくはNR24によって場合により中断されたC3−C20シクロアルキル、あるいはフェニル、ナフチル、フェニル−C1−C4アルキル、SR4、OR3またはNR17R18であり;
R20は、COOR3、CONR5R6、(CO)R1であり;あるいは
R20は、R5およびR6について示されている意味の1つを有し;
R21は、COOR3、CONR5R6、(CO)R1であり;あるいは
R21は、R3について示されている意味の1つを有し;
R22は、水素、C1−C20アルキル;C2−C20アルケニル;O、S、COまたはNR5によって場合により中断されたC3−C20シクロアルキルであり、あるいはC3−C10シクロアルケニルであり;あるいは1つ以上のハロゲン、SR4、OR3、COOR3、NR5R6、C1−C20ヘテロアリール、C1−C20ヘテロアリール−(CO)O、CONR5R6、
R22は、C2−C20アルカノイル、または非置換であるか、または1つ以上のC1−C6アルキル、ハロゲン、フェニル、SR4、OR3もしくはNR5R6によって置換されたベンゾイルであり;あるいは
R22は、1つ以上のOによって場合により中断され、かつ/または1つ以上のOHによって場合により置換されたC2−C12アルコキシカルボニルであり;あるいは
R22は、非置換であるか、または1つ以上のC1−C6アルキル、C1−C4ハロアルキル、ハロゲン、フェニル、SR4、OR3もしくはNR5R6によって置換されたフェノキシカルボニルであり;あるいは
R22はNR5R6であり;あるいは
R22は、基
R23は、R1について示されている意味の1つを有し;且つ
R24は、水素、C1−C20アルキル、C1−C4ハロアルキル、O、SもしくはCOによって中断されたC2−C20アルキルであり、あるいはフェニル−C1−C4アルキル、O、SもしくはCOによって場合により中断されたC3−C20シクロアルキルであり、あるいはフェニルである]の化合物である。
R2およびR’2は、互いに独立して、非置換C1−C20アルキル、またはCOOR3もしくは
X1はOであり;
R3は、C1−C20アルキル、C1−C8アルカノイルまたはフェニル−C1−C3アルキルであり;あるいはR3は、Oによって場合により中断されたC3−C20シクロアルキル、特にC1−C20アルキルまたはC1−C8アルカノイルであり;
R4は、C1−C20アルキル、C1−C8アルカノイル、フェニル−C1−C3アルキルまたはC1−C20ヘテロアリールであり;あるいはR4は、非置換であるか、またはC1−C20アルキル、ハロゲンもしくは
R5およびR6は、互いに独立して、水素、フェニルまたはC1−C20アルキルであり;R5およびR6は、それらが結合したN原子と一緒になって、複素芳香族環系、特にカルバゾリルを形成し;
R7は、それぞれが1つ以上のC1−C6アルキル、ハロゲン、CN、OR3、SR4またはNR5R6によって場合により置換されたフェニル、ナフチルまたはC1−C20ヘテロアリール、特に、それぞれが1つ以上のC1−C6アルキル、ハロゲン、OR3、SR4またはNR5R6によって場合により置換されたフェニル、ナフチルまたはC1−C20ヘテロアリールであり;
R8およびR9は水素であり;
R20は(CO)R1であり;
R21は(CO)R1である式Iの化合物が好適である。
R2およびR’2は、互いに独立して、非置換C1−C20アルキル、またはCOOR3によって置換されたC1−C20アルキルであり;
R3は、C1−C20アルキルまたはC1−C8アルカノイルであり;
R4はフェニルであり;
R5およびR6は、それらが結合したN原子と一緒になって、複素芳香族環系、特にカルバゾリルを形成し;
R7は、それぞれが1つ以上のC1−C6アルキル、ハロゲン、OR3、SR4またはNR5R6によって場合により置換されたフェニル、ナフチルまたはC1−C20ヘテロアリールであり;
R8およびR9は水素である、以上に定義されている式Iの化合物が特に好適である。
R2およびR’2は、互いに独立して、非置換C1−C20アルキル、またはSR4もしくはCOOR3によって置換されたC1−C20アルキルであり;あるいはR2およびR’2は、
mは1であり;
X2は直接結合であり;
R3は、C1−C20アルキルまたはフェニル−C1−C3アルキルであり;あるいはR3は、Oによって場合により中断されたC3−C20シクロアルキルであり、特に、R3はC1−C20アルキルまたはC1−C8アルカノイルであり;
R4は、C1−C20アルキル、C1−C8アルカノイル、フェニル−C1−C3アルキルまたはC1−C20ヘテロアリールであり;あるいはR4は、非置換であるか、またはC1−C20アルキル、ハロゲンもしくは
R5およびR6は、互いに独立して、水素、フェニルまたはC1−C20アルキルであり;R5およびR6は、それらが結合したN原子と一緒になって、非置換であるか、または
R''1は、R1について示されている意味の1つを有し;
R''2は、R2について示されている意味の1つを有し;
R7は、それぞれが1つ以上のC1−C6アルキル、ハロゲン、CN、OR3、SR4またはNR5R6によって場合により置換されたフェニル、ナフチルまたはC1−C20ヘテロアリールであり、特に、R7は、それぞれが1つ以上のC1−C6アルキル、ハロゲン、OR3、SR4またはNR5R6によって場合により置換されたフェニル、ナフチルまたはC1−C20ヘテロアリールであり;
R8およびR9は水素であり;
R22はC1−C20アルキルであり;
R23は、R1について示されている意味の1つを有し、特に、R23はC1−C20アルキルである、以上に定義されている式Iまたは(I’)の化合物が好適である。
R2およびR’2は、互いに独立して、非置換C1−C20アルキル、またはSR4もしくはCOOR3によって置換されたC1−C20アルキルであり;あるいはR2およびR’2は、
mは1であり;
X2は直接結合であり;
R3は、C1−C20アルキルまたはC1−C8アルカノイルであり;
R4は、C1−C20ヘテロアリール、または非置換であるか、またはNO2または
R5およびR6は、それらが結合したN原子と一緒になって、非置換であるか、または
R''1は、R1について示されている意味の1つを有し;
R''2は、R2について示されている意味の1つを有し;
R7は、それぞれが1つ以上のC1−C6アルキル、ハロゲン、OR3、SR4またはNR5R6によって場合により置換されたフェニル、ナフチルまたはC1−C20ヘテロアリールであり;
R8およびR9は水素であり;
R22はC1−C20アルキルであり;
R23はC1−C20アルキルである、以上に定義されている式IおよびI’の化合物が特に興味深い。
Halはハロゲン、特にClであり、
R1およびR’1は、以上に定義されている通りである]のハロゲン化アシル、あるいは式IV
(a)少なくとも1つのエチレン性不飽和光重合性化合物と、
(b)光開始剤として、以上に定義されている式IまたはI’の少なくとも1つの化合物と、を含む光重合性組成物である。
トリメチロールプロパントリアクリレート、トリメチロールエタントリアクリレート、トリメチロールプロパントリメタクリレート、トリメチロールエタントリメタクリレート、テトラメチレングリコールジメタクリレート、トリエチレングリコールジメタクリレート、テトラエチレングリコールジアクリレート、ペンタエリスリトールジアクリレート、ペンタエリスリトールトリアクリレート、ペンタエリスリトールテトラアクリレート、ジペンタエリスリトールジアクリレート、ジペンタエリスリトールトリアクリレート、ジペンタエリスリトールテトラアクリレート、ジペンタエリスリトールペンタアクリレート、ジペンタエリスリトールヘキサアクリレート、トリペンタエリスリトールオクタアクリレート、ペンタエリスリトールジメタアクリレート、ペンタエリスリトールトリメタクリレート、ジペンタエリスリトールジメタクリレート、ジペンタエリスリトールテトラメタクリレート、トリペンタエリスリトールオクタメタクリレート、ペンタエリスリトールジイタコネート、ジペンタエリスリトールトリス−イタコネート、ジペンタエリスリトールペンタイタコネート、ジペンタエリスリトールヘキサイタコネート、エチレングリコールジアクリレート、1,3−ブタンジオールジアクリレート、1,3−ブタンジオールジメタクリレート、1,4−ブタンジオールジイタコネート、ソルビトールトリアクリレート、ソルビトールテトラアクリレート、ペンタエリスリトール変性トリアクリレート、ソルビトールテトラメタクリレート、ソルビトールペンタアクリレート、ソルビトールヘキサアクリレート、オリゴエステルアクリレートおよびメタクリレート、グリセロールジアクリレートおよびトリアクリレート、1,4−シクロヘキサンジアクリレート、200〜1500の分子量を有するポリエチレングリコールのビスアクリレートおよびビスメタクリレート、またはそれらの混合物である。
1.2−(2’−ヒドロキシフェニル)ベンゾトリアゾール、例えば、2−(2’−ヒドロキシ−5’−メチルフェニル)ベンゾトリアゾール、2−(3’,5’−ジ−tert−ブチル−2’−ヒドロキシフェニル)ベンゾトリアゾール、2−(5’−tert−ブチル−2’−ヒドロキシフェニル)ベンゾトリアゾール、2−(2’−ヒドロキシ−5’−(1,1,3,3−テトラメチルブチル)フェニル)ベンゾトリアゾール、2−(3’,5’−ジ−tert−ブチル−2’−ヒドロキシフェニル)−5−クロロベンゾトリアゾール、2−(3’−tert−ブチル−2’−ヒドロキシ−5’−メチルフェニル)−5−クロロベンゾトリアゾール、2−(3’−sec−ブチル−5’−tert−ブチル−2’−ヒドロキシフェニル)ベンゾトリアゾール、2−(2’−ヒドロキシ−4’−オクトキシフェニル)ベンゾトリアゾール、2−(3’,5’−ジ−tert−アミル−2’−ヒドロキシフェニル)ベンゾトリアゾール、2−(3’,5’−ビス(α,α−ジメチルベンジル)−2’−ヒドロキシフェニル)ベンゾトリアゾール、2−(3’−tert−ブチル−2’−ヒドロキシ−5’−(2−オクチルオキシカルボニルエチル)フェニル)−5−クロロベンゾトリアゾール、2−(3’−tert−ブチル−5’−[2−(2−エチル−ヘキシル−オキシ)カルボニルエチル]−2’−ヒドロキシフェニル)−5−クロロベンゾトリアゾール、2−(3’−tert−ブチル−2’−ヒドロキシ−5’−(2−メトキシカルボニルエチル)フェニル)−5−クロロベンゾトリアゾール、2−(3’−tert−ブチル−2’−ヒドロキシ−5’−(2−メトキシカルボニルエチル)フェニル)−ベンゾトリアゾール、2−(3’−tert−ブチル−2’−ヒドロキシ−5’−(2−オクチルオキシカルボニルエチル)フェニル)ベンゾトリアゾール、2−(3’−tert−ブチル−5’−[2−(2−エチルヘキシルオキシ)カルボニルエチル]−2’−ヒドロキシフェニル)ベンゾトリアゾール、2−(3’−ドデシル−2’−ヒドロキシ−5’−メチルフェニル)ベンゾトリアゾールおよび2−(3’−tert−ブチル−2’−ヒドロキシ−5’−(2−イソオクチルオキシカルボニルエチル)フェニルベンゾトリアゾールの混合物、2,2’−メチレン−ビス[4−(1,1,3,3−テトラメチルブチル)−6−ベンゾトリアゾール−2−イル−フェノール];2−[3’−tert−ブチル−5’−(2−メトキシカルボニルエチル)−2’−ヒドロキシ−フェニル]−ベンゾトリアゾールとポリエチレングリコール300とのエステル交換生成物;[R−CH2CH2−COO(CH2)3]2−(式中、R=3’−tert−ブチル−4’−ヒドロキシ−5’−2H−ベンゾトリアゾール−2−イル−フェニル];
2.2−ヒドロキシベンゾフェノン、例えば、4−ヒドロキシ−、4−メトキシ−、4−オクトキシ−、4−デシルオキシ−、4−ドデシルオキシ−、4−ベンジルオキシ−、4,2’、4’−トリヒドロキシ−および2’−ヒドロキシ−4,4’−ジメトキシ誘導体;
3.置換または非置換安息香酸のエステル、例えば、サリチル酸4−tert−ブチルフェニル、サリチル酸フェニル、サリチル酸オクチルフェニル、ジベンゾイルレソルシノール、ビス(4−tert−ブチルベンゾイル)レソルシノール、ベンゾイルレソルシノール、2,4−ジ−tert−ブチルフェニル、3,5−ジ−tert−ブチル−4−ヒドロキシベンゾエート、3,5−ジ−tert−ブチル−4−ヒドロキシ安息香酸ヘキサデシル、3,5−ジ−tert−ブチル−4−ヒドロキシ安息香酸オクタデシルおよび3,5−ジ−tert−ブチル−4−ヒドロキシ安息香酸2−メチル−4,6−ジ−tert−ブチルフェニル;
4.アクリレート、例えば、イソオクチルまたはエチルα−シアノ−β,β−ジフェニルアクリレート、メチルα−カルボメトキシシナメート、ブチルもしくはメチルα−シアノ−β−メチル−p−メトキシシナメート、メチルα−カルボキシメトキシ−p−メトキシシナメートおよびN−(β−カルボメトキシ−β−シアノビニル)−2−メチルインドリン;
5.立体阻害アミン、例えば、ビス(2,2,6,6−テトラメチルピペリジル)セバケート、ビス(2,2,6,6−テトラメチルピペリジル)スクシネート、ビス(1,2,2,6,6−ペンタメチルピペリジル)セバケート、ビス(1,2,2,6,6−ペンタメチルピペリジル)n−ブチル−3,5−ジ−tert−ブチル−4−ヒドロキシベンジルマロネート、1−ヒドロキシエチル−2,2,6,6−テトラメチル−4−ヒドロキシピペリジンとコハク酸の縮合生成物、N,N’−ビス(2,2,6,6−テトラメチル−4−ピペリジル)ヘキサ−メチレンジアミンと4−tert−オクチルアミノ−2,6−ジクロロ−1,3,5−s−トリアジンの縮合生成物、トリス−(2,2,6,6−テトラメチル−4−ピペリジル)ニトリロトリアセテート、テトラキス−(2,2,6,6−テトラメチル−4−ピペリジル)−1,2,3,4−ブタンテトラオエート、1,1’−(1,2−エタンジイル)ビス(3,3,5,5−テトラメチル−ピペラジノン)、4−ベンゾイル−2,2,6,6−テトラメチルピペリジン、4−ステアリルオキシ−2,2,6,6−テトラメチルピペリジン、ビス−(1,2,2,6,6−ペンタメチルピペリジル)2−n−ブチル−2−(2−ヒドロキシ−3,5−ジ−tert−ブチルベンジル)マロネート、3−n−オクチル−7,7,9,9−テトラメチル−1,3,8−トリアザスピロ−[4.5]デカン−2,4−ジオン、ビス−(1−オクチルオキシ−2,2,6,6−テトラメチルピペリジル)セバケート、ビス−(1−オクチルオキシ−2,2,6,6−テトラメチルピペリジル)スクシネート、N,N’−ビス−(2,2,6,6−テトラ−メチル−4−ピペリジル)ヘキサメチレンジアミンと4−モルホリノ−2,6−ジクロロ−1,3,5−トリアジンの縮合生成物、2−クロロ−4,6−ジ−(4−n−ブチルアミノ−2,2,6,6−テトラメチルピペリジル)−1,3,5−トリアジンと1,2−ビス−(3−アミノプロピル−アミノ)エタンの縮合生成物、2−クロロ−4,6−ジ−(4−n−ブチルアミノ−1,2,2,6,6−ペンタメチルピペリジル)−1,3,5−トリアジンと1,2−ビス−(3−アミノプロピルアミノ)エタンの縮合生成物、8−アセチル−3−ドデシル−7,7,9,9−テトラメチル−1,3,8−トリアザスピロ[4.5]デカン−2,4−ジオン、3−ドデシル−1−(2,2,6,6−テトラメチル−4−ピペリジル)ピロリジン−2,5−ジオンおよび3−ドデシル−1−(1,2,2,6,6−ペンタメチル−4−ピペリジル)−ピロリジン−2,5−ジオン;
6.オキサルアミド、例えば、4,4’−ジオクチルオキシオキサニリド、2,2’−ジエトキシオキサニリド、2,2’−ジオクチルオキシ−5,5’−ジ−tert−ブチルオキサニリド、2,2’−ジドデシルオキシ−5,5’−ジ−tert−ブチルオキサニリド、2−エトキシ−2’−エチルオキサニリド、N,N’−ビス−(3−ジメチルアミノプロピル)オキサルアミド、2−エトキシ−5−tert−ブチル−2’−エチルオキサニリドおよびその2−エトキシ−2’−エチル−5,4’−ジ−tert−ブチルオキサニリドとの混合物、o−およびp−メトキシならびにo−およびp−エトキシ−二置換オキサニリドの混合物;
7.2−(2−ヒドロキシフェニル)−1,3,5−トリアジン、例えば、2,4,6−トリス(2−ヒドロキシ−4−オクチルオキシフェニル)−1,3,5−トリアジン、2−(2−ヒドロキシ−4−オクチルオキシフェニル)−4,6−ビス−(2,4−ジメチルフェニル)−1,3,5−トリアジン、2−(2,4−ジヒドロキシフェニル)−4,6−ビス(2,4−ジメチルフェニル)−1,3,5−トリアジン、2,4−ビス(2−ヒドロキシ−4−プロピルオキシ−フェニル)−6−(2,4−ジメチルフェニル)−1,3,5−トリアジン、2−(2−ヒドロキシ−4−オクチルオキシフェニル)−4,6−ビス(4−メチルフェニル)−1,3,5−トリアジン、2−(2−ヒドロキシ−4−ドデシルオキシフェニル)−4,6−ビス(2,4−ジメチルフェニル)−1,3,5−トリアジン、2−[2−ヒドロキシ−4−(2−ヒドロキシ−3−ブチルオキシ−プロピルオキシ)フェニル]−4,6−ビス(2,4−ジメチルフェニル)−1,3,5−トリアジン、2−[2−ヒドロキシ−4−(2−ヒドロキシ−3−オクチルオキシ−プロピルオキシ)フェニル]−4,6−ビス(2,4−ジ−メチルフェニル)−1,3,5−トリアジン、2−[4−ドデシル/トリデシル−オキシ−(2−ヒドロキシプロピル)オキシ−2−ヒドロキシ−フェニル]−4,6−ビス(2,4−ジメチルフェニル)−1,3,5−トリアジン;
8.ホスファイトおよびホスホナイト、例えば、トリフェニルホスファイト、ジフェニルアルキルホスファイト、フェニルジアルキルホスファイト、トリス(ノニルフェニル)ホスファイト、トリラウリルホスファイト、トリオクタデシルホスファイト、ジステアリルペンタエリスリチルジホスファイト、トリス−(2,4−ジ−tert−ブチルフェニル)ホスファイト、ジイソデシルペンタエリスリチルジホスファイト、ビス−(2,4−ジ−tert−ブチルフェニル)ペンタエリスリチルジホスファイト、ビス−(2,6−ジ−tert−ブチル−4−メチルフェニル)ペンタエリスリチルジホスファイト、ビス−イソデシルオキシペンタエリスリチルジホスファイト、ビス−(2,4−ジ−tert−ブチル−6−メチルフェニル)ペンタエリスリチルジホスファイト、ビス−(2,4,6−トリ−tert−ブチルフェニル)ペンタエリスリチルジホスファイト、トリステアリルソルビチルトリホスファイト、テトラキス(2,4−ジ−tert−ブチルフェニル)−4,4’−ビフェニレンジホスホナイト、6−イソオクチルオキシ−2,4,8,10−テトラ−tert−ブチル−12H−ジベンゾ[d,g]−1,3,2−ジオキサホスホシン、6−フルオロ−2,4,8,10−テトラ−tert−ブチル−12−メチル−ジベンゾ[d,g]−1,3,2−ジオキサホスホシン、ビス−(2,4−ジ−tert−ブチル−6−メチルフェニル)メチルホスファイトおよびビス(2,4−ジ−tert−ブチル−6−メチルフェニル)エチルホスファイトである。
1.チオキサトン
チオキサントン、2−イソプロピルチオキサントン、2−クロロチオキサントン、1−クロロ−4−プロポキシチオキサントン、2−ドデシルチオキサントン、2,4−ジエチルチオキサントン、2,4−ジメチルチオキサントン、1−メトキシ−カルボニルチオキサントン、2−エトキシカルボニルチオキサントン、3−(2−メトキシエトキシカルボニル)−チオキサントン、4−ブトキシカルボニルチオキサントン、3−ブトキシカルボニル−7−メチルチオキサントン、1−シアノ−3−クロロチオキサントン、1−エトキシカルボニル−3−クロロチオキサントン、1−エトキシカルボニル−3−エトキシチオキサントン、1−エトキシカルボニル−3−アミノチオキサントン、1−エトキシカルボニル−3−フェニルスルフリルチオキサントン、3,4−ジ−[2−(2−メトキシエトキシ)エトキシカルボニル]−チオキサントン、1,3−ジメチル−2−ヒドロキシ−9H−チオキサンテン−9−オン2−エチルヘキシルエーテル、1−エトキシカルボニル−3−(1−メチル−1−モルホリノエチル)−チオキサントン、2−メチル−6−ジメトキシメチル−チオキサントン、2−メチル−6−(1,1−ジメトキシベンジル)−チオキサントン、2−モルホリノメチルチオキサントン、2−メチル−6−モルホリノメチルチオキサントン、N−アリルチオキサントン−3,4−ジカルボキシイミド、N−オクチルチオキサントン−3,4−ジカルボキシイミド、N−(1,1,3,3−テトラメチルブチル)−チオキサントン−3,4−ジカルボキシイミド、1−フェノキシチオキサントン、6−エトキシカルボニル−2−メトキシチオキサントン、6−エトキシカルボニル−2−メチルチオキサントン、チオキサントン−2−カルボン酸ポリエチレングリコールエステル、2−ヒドロキシ−3−(3,4−ジメチル−9−オキソ−9H−チオキサントン−2−イルオキシ)−N,N,N−トリメチル−1−プロパンアミニウム塩化物;
2.ベンゾフェノン
ベンゾフェノン、4−フェニルベンゾフェノン、4−メトキシベンゾフェノン、4,4’−ジメトキシベンゾフェノン、4,4’−ジメチルベンゾフェノン、4,4’−ジクロロベンゾフェノン、4,4’−ビス(ジメチルアミノ)−ベンゾフェノン、4,4’−ビス(ジエチルアミノ)ベンゾフェノン、4,4’−ビス(メチルエチルアミノ)ベンゾフェノン、4,4’−ビス(p−イソプロピルフェノキシ)ベンゾフェノン、4−メチルベンゾフェノン、2,4,6−トリメチルベンゾフェノン、4−(4−メチルチオフェニル)ベンゾフェノン、3,3’−ジメチル−4−メトキシベンゾフェノン、メチル−2−ベンゾイルベンゾエート、4−(2−ヒドロキシエチルチオ)−ベンゾフェノン、4−(4−トリルチオ)−ベンゾフェノン、1−[4−(4−ベンゾイル−フェニルスルファニル)−フェニル]−2−メチル−2−(トルエン−4−スルホニル)−プロパン−1−オン、4−ベンゾイル−N,N,N−トリメチルベンゼンメタンアミニウム塩化物、2−ヒドロキシ−3−(4−ベンゾイルフェノキシ)−N,N,N−トリメチル−1−プロパンアミニウム塩化物一水和物、4−(13−アクリロイル−1,4,7,10,13−ペンタオキサトリデシル)−ベンゾフェノン、4−ベンゾイル−N,N−ジメチル−N−[2−(1−オキソ−2−プロペニル)オキシ]エチル−ベンゼンメタンアミニウム塩化物;
3.クマリン
クマリン1、クマリン2、クマリン6、クマリン7、クマリン30、クマリン102、クマリン106、クマリン138、クマリン152、クマリン153、クマリン307、クマリン314、クマリン314T、クマリン334、クマリン337、クマリン500、3−ベンゾイルクマリン、3−ベンゾイル−7−メトキシクマリン、3−ベンゾイル−5,7−ジメトキシクマリン、3−ベンゾイル−5,7−ジプロポキシクマリン、3−ベンゾイル−6,8−ジクロロクマリン、3−ベンゾイル−6−クロロ−クマリン、3,3’−カルボニル−ビス[5,7−ジ(プロポキシ)−クマリン]、3,3’−カルボニル−ビス(7−メトキシクマリン)、3,3’−カルボニル−ビス(7−ジエチルアミノ−クマリン)、3−イソブチロイルクマリン、3−ベンゾイル−5,7−ジメトキシ−クマリン、3−ベンゾイル−5,7−ジエトキシ−クマリン、3−ベンゾイル−5,7−ジブトキシクマリン、3−ベンゾイル−5,7−ジ(メトキシエトキシ)−クマリン、3−ベンゾイル−5,7−ジ(アリルオキシ)クマリン、3−ベンゾイル−7−ジメチルアミノクマリン、3−ベンゾイル−7−ジエチルアミノクマリン、3−イソブチロイル−7−ジメチルアミノクマリン、5,7−ジメトキシ−3−(1−ナフトイル)−クマリン、5,7−ジエトキシ−3−(1−ナフトイル)−クマリン、3−ベンゾイルベンゾ[f]クマリン、7−ジエチルアミノ−3−チエノイルクマリン、3−(4−シアノベンゾイル)−5,7−ジメトキシクマリン、3−(4−シアノベンゾイル)−5,7−ジプロポキシクマリン、7−ジメチルアミノ−3−フェニルクマリン、7−ジエチルアミノ−3−フェニルクマリン、JP09−179299−AおよびJP09−325209−Aに開示されているクマリン誘導体、例えば、7−[{4−クロロ−6−(ジエチルアミノ)−S−トリアジン−2−イル}アミノ]−3−フェニルクマリン;
4.3−(アロイルメチレン)−チアゾリン
3−メチル−2−ベンゾイルメチレン−β−ナフトチアゾリン、3−メチル−2−ベンゾイルメチレン−ベンゾチアゾリン、3−エチル−2−プロピオニルメチレン−β−ナフトチアゾリン;
5.ロダニン
4−ジメチルアミノベンザルロダニン、4−ジエチルアミノベンザルロダニン、3−エチル−5−(3−オクチル−2−ベンゾチアゾリニリデン)−ロダニン、ロダニン誘導体、JP08−305019Aに開示されている式[1]、[2]、[7];
6.他の化合物
アセトフェノン、3−メトキシアセトフェノン、4−フェニルアセトフェノン、ベンジル、4,4’−ビス(ジメチルアミノ)ベンジル、2−アセチルナフタレン、2−ナフタルデヒド、ダンシル酸誘導体、9,10−アントラキノン、アントラセン、ピレン、アミノピレン、ペリレン、フェナントレン、フェナントレンキノン、9−フルオレノン、ジベンゾスベロン、クルクミン、キサントン、チオミヒラーケトン、α−(4−ジメチルアミノベンジリデン)ケトン、例えば、2,5−ビス(4−ジエチルアミノベンジリデン)シクロペンタノン、2−(4−ジメチルアミノ−ベンジリデン)−インダン−1−オン、3−(4−ジメチルアミノ−フェニル)−1−インダン−5−イル−プロペノン、3−フェニルチオフタルイミド、N−メチル−3,5−ジ(エチルチオ)−フタルイミド、N−メチル−3,5−ジ(エチルチオ)−フタルイミド、フェノチアジン、メチルフェノチアジン、アミン、例えば、N−フェニルグリシン、4−ジメチルアミノ安息香酸エチル、4−ジメチルアミノ安息香酸ブトキシエチル、4−ジメチルアミノアセトフェノン、トリエタノールアミン、メチルジエタノールアミン、ジメチルアミノエタノール、2−(ジメチルアミノ)エチルベンゾエート、ポリ(プロピレングリコール)−4−(ジメチルアミノ)ベンゾエートである。
R100は−COCH=CH2または−COC(CH3)=CH2であり、
pは、0〜6(pの合計:3〜24)であり、qは0〜6(qの合計:2〜16)である]に示されるペンタエリスリトールおよびジペンタエリスリトール誘導体である。
Y10は、
CH2=CHA100−Y100−A200−SO2−NH−A3(a)
CH2=CHA400−Y200−A500−NH−SO2−A600(b)
式中、Y100およびY200は、それぞれ−COO−、−CONA700−または一重結合を表し;A100およびA400は、それぞれHまたはCH3を表し;A200およびA500は、それぞれ、置換基を場合により有するC1−C12アルキレン、シクロアルキレン、アリーレンもしくはアラルキレン、またはエーテル基およびチオエーテル基が挿入されたC2−C12アルキレン、シクロアルキレン、アリーレンもしくはアラルキレンを表し;A300およびA600は、それぞれ、H、置換基を場合により有するC1−C12アルキル、シクロアルキル基、アリール基またはアラルキル基を表し;A700は、H、置換基を場合により有するC1−C12アルキル、シクロアルキル基、アリール基またはアラルキル基を表す。
−本発明の式IまたはI’の光開始剤化合物と、
−有機結合剤、特に、カルボキシル基を有するアクリル酸エポキシ樹脂である有機結合剤と、
−黒色着色材料と、
−ポリマー分散剤、特に、塩基性官能基を含むポリマー分散剤と、
を含む。
[式Iの化合物;R1=R2=CH3;R7=CH3によって置換されたフェニル]
1.a.1−(4−{(4−アセチル−フェニル)−[4−(3−メチル−ベンゾイル)−フェニル]−アミノ}−フェニル)−エタノン
CH2Cl2(80mL)中トリフェニルアミン(5.00g)に対して、AlCl3(2.89g)および塩化m−トルオイル(3.15g)を0℃で添加する。室温で終夜撹拌した後、AlCl3(5.98g)および塩化アセチル(3.36g)を0℃でさらに添加する。混合物を室温で終夜撹拌した後、反応混合物を氷水に注ぎ込み、粗製物をCH2Cl2で2回抽出する。一緒にした有機層をH2Oおよび塩水で洗浄し、MgSO4で乾燥させ、濃縮して製造物を得る。黄色固体として得られた製造物の構造を1H−NMRスペクトル(CDCl3)によって確認する。
WO02−100903に記載の手順に従って、ケトン1.aを、黄色固体として単離された、対応する酢酸オキシム1.bに変換する。構造を1H−NMRスペクトル(CDCl3)によって確認する。
実施例2〜15の化合物を、実施例1またはUS6596445、あるいは適切な抽出物を採用するWO2007/062963に示される方法に従って調製する。化合物およびそれらの物理データを以下の表1に掲載する。
実施例26:ポリ(ベンジルメタクリレート−コ−メタクリル酸)の調製
24gのベンジルメタクリレート、6gのメタクリル酸および0.525gのアゾビスイソブチロニトリル(AIBN)を90mlのプロピレングリコール1−モノメチルエーテル2−アセテート(PGMEA)に溶解させる。得られた反応混合物を、80℃の予め加熱された油浴に入れる。80℃にて窒素下で5時間撹拌した後、得られた粘性溶液を室温まで冷却し、さらに精製することなく使用する。固形分は約25%である。
以下の成分を混合することによって、感度試験のための光硬化性組成物を調製する。
200.0質量部のベンジルメタクリレートとメタクリル酸のコポリマー
(ベンジルメタクリレート:メタクリル酸=80:20(質量比))
25%プロピレングリコール1−モノメチルエーテル2−アセテート
上記実施例で調製した(PGMEA)溶液
50質量部のジペンタエリスリトールヘキサアクリレート(UCB Chemicalsによって提供された(DPHA))、
2.0質量部の光開始剤、および
150.0質量部のPGMEA
Claims (15)
- 式IまたはI’
R1およびR’1は、C 1 −C 12 アルキル、フェニルまたはC 1 −C 8 アルコキシであり;、
R2およびR’2は、互いに独立して、非置換C 1 −C 20 アルキル、またはSR 4 もしくはCOOR 3 によって置換されたC 1 −C 20 アルキルであり;あるいはR 2 およびR’ 2 は、
mは1であり;
X 2 は、直接結合であり;
R 3 は、C 1 −C 20 アルキルまたはフェニル−C 1 −C 3 アルキルであり;あるいはR 3 は、Oによって場合により中断されたC 3 −C 20 シクロアルキルであり、
R 4 は、C 1 −C 20 アルキル、C 1 −C 8 アルカノイル、フェニル−C 1 −C 3 アルキルまたはC 1 −C 20 ヘテロアリールであり;あるいはR 4 は、非置換であるか、またはC 1 −C 20 アルキル、ハロゲンもしくは
R 5 およびR 6 は、互いに独立して、水素、フェニルまたはC 1 −C 20 アルキルであり;R 5 およびR 6 は、それらが結合したN原子と一緒になって、非置換であるか、または
R''1は、R1について示されている意味の1つを有し;
R''2は、R2について示されている意味の1つを有し;
R 7 は、それぞれが1つ以上のC 1 −C 6 アルキル、ハロゲン、CN、OR 3 、SR 4 またはNR 5 R 6 によって場合により置換されたフェニル、ナフチルまたはC 1 −C 20 ヘテロアリールであり、;
R 8 およびR 9 は水素であり;
R 22 はC 1 −C 20 アルキルであり;且つ
R23は、R1について示されている意味の1つを有する]の化合物。 - (a)少なくとも1つのエチレン性不飽和光重合性化合物と、
(b)光開始剤としての請求項1に定義された少なくとも1つの式IまたはI’の化合物と
を含む光重合性組成物。 - 成分(a)が、飽和または不飽和多塩基酸無水物と、エポキシ樹脂と不飽和モノカルボン酸との反応生成物との反応によって得られる樹脂である、請求項2に記載の光重合性組成物。
- 光開始剤(b)に加えて、少なくとも1つのさらなる光開始剤(c)および/または他の添加剤(d)を含む、請求項2に記載の光重合性組成物。
- さらなる添加剤(d)として顔料または顔料の混合物を含む、請求項4に記載の光重合性組成物。
- さらなる添加剤(d)として分散剤または分散剤の混合物を含む、請求項5に記載の光重合性組成物。
- 組成物に対して0.05〜25質量%の光開始剤(b)または光開始剤(b)および(c)を含む、請求項2〜6のいずれか一項に記載の光重合性組成物。
- さらなる添加剤(d)として光増感剤を含む、請求項2〜7のいずれか一項に記載の光重合性組成物。
- 結合剤ポリマー(e)をさらに含む、請求項2〜8のいずれか一項に記載の光重合性組成物。
- エチレン性不飽和二重結合を含む化合物を光重合するための方法であって、請求項2〜9のいずれか一項に記載の組成物に150〜600nmの範囲の電磁放射線、または電子ビームもしくはX線を照射することを含む方法。
- 着色若しくは非着色ペイント又はワニス、粉末塗料、印刷インク、印刷板、接着剤、感圧接着剤、歯科組成物、ゲルコート、電子部品用フォトレジスト、電気メッキレジスト、エッチングレジスト、はんだレジスト、ディスプレイ用途のカラーフィルタを製造するためのレジスト、プラズマディスプレイパネル、エレクトロルミネセンスディスプレイ又はLCDの製造過程における構造体を生成するためのレジスト、LCDのためのスペーサの製造のための、ホログラフデータ記憶(HDS)のための、電気および電子部品を封入するための組成物としての、磁気記録材料、微小機械部品、導波管、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、ガラス繊維ケーブル塗料、スクリーン印刷ステンシルの製造のための、光造形による三次元物体の製造のための、画像記録材料としての、ホログラフ記録装置、微小電子回路、マイクロカプセルを使用する画像記録材料のための、UVおよび可視レーザ直接映像システムのためのフォトレジスト材料としての、又は、印刷回路基板の順次積層における誘電層を形成するのに使用されるフォトレジスト材料としての、請求項2〜9のいずれか一項に記載の組成物の使用。
- いずれも感光性樹脂および顔料を含む赤色、緑色および青色画素ならびに黒色マトリックスを透明基板上に設け、透明電極を基板の表面またはカラーフィルタ層の表面のいずれかに設けることによって製造されるカラーフィルタであって、前記感光性樹脂は、多官能性アクリレートモノマー、有機ポリマー結合剤および請求項1に定義された式IまたはI’の光重合開始剤を含む、カラーフィルタ。
- 少なくとも1つの表面が請求項2に記載の組成物で塗装された塗装基板。
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TW (1) | TWI466853B (ja) |
WO (1) | WO2009147031A2 (ja) |
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JP5553827B2 (ja) * | 2008-06-06 | 2014-07-16 | ビーエーエスエフ ソシエタス・ヨーロピア | 光開始剤混合物 |
CN102203136B (zh) * | 2008-11-03 | 2013-11-13 | 巴斯夫欧洲公司 | 光敏引发剂混合物 |
JP5799799B2 (ja) * | 2011-10-20 | 2015-10-28 | 日立化成株式会社 | 感光性樹脂組成物、感光性エレメント、レジストパターンの形成方法及びプリント配線板の製造方法 |
CN107652383A (zh) * | 2011-10-20 | 2018-02-02 | 日立化成株式会社 | 感光性树脂组合物、感光性元件、抗蚀图形的形成方法以及印刷电路板的制造方法 |
WO2013083505A1 (en) | 2011-12-07 | 2013-06-13 | Basf Se | Oxime ester photoinitiators |
CN103698976A (zh) * | 2012-09-27 | 2014-04-02 | 李妤 | 新型激光数字全息高密度存储显示材料的制备 |
WO2014097595A1 (ja) * | 2012-12-21 | 2014-06-26 | 日立化成デュポンマイクロシステムズ株式会社 | 感光性樹脂組成物、それを用いたパターン硬化膜の製造方法及び半導体装置 |
CN105531260B (zh) | 2013-09-10 | 2019-05-31 | 巴斯夫欧洲公司 | 肟酯光引发剂 |
CN103819583B (zh) * | 2014-03-18 | 2016-05-18 | 常州强力电子新材料股份有限公司 | 一种含硝基双肟酯类光引发剂及其制备方法和应用 |
CN104672354A (zh) * | 2015-02-04 | 2015-06-03 | 天津墨森科技有限公司 | 一种双肟酯类光引发剂及其制备方法和应用 |
JP6775508B2 (ja) * | 2015-08-24 | 2020-10-28 | 株式会社Adeka | オキシムエステル化合物及び該化合物を含有する重合開始剤 |
JP6713112B2 (ja) * | 2016-04-27 | 2020-06-24 | 東京応化工業株式会社 | 化合物及びその製造方法 |
TWI664500B (zh) * | 2016-06-30 | 2019-07-01 | 奇美實業股份有限公司 | 黑色感光性樹脂組成物及其應用 |
KR102545326B1 (ko) * | 2017-03-16 | 2023-06-21 | 가부시키가이샤 아데카 | 옥심에스테르 화합물 및 상기 화합물을 함유하는 광중합 개시제 |
CN109134710B (zh) * | 2017-06-15 | 2021-08-03 | 常州强力电子新材料股份有限公司 | 一种芳基硫鎓盐肟酯类光引发剂及其合成与应用 |
CN109134711B (zh) * | 2017-06-15 | 2021-08-03 | 常州强力电子新材料股份有限公司 | 一种硫鎓盐光引发剂及其制备与应用 |
KR102355406B1 (ko) * | 2017-06-29 | 2022-01-25 | 스미또모 가가꾸 가부시키가이샤 | 착색 경화성 수지 조성물, 컬러 필터 및 표시 장치 |
JP2020200272A (ja) * | 2019-06-11 | 2020-12-17 | 株式会社Adeka | カルバモイルオキシム化合物並びに該化合物を含有する重合開始剤及び重合性組成物 |
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WO2008138732A1 (en) | 2007-05-11 | 2008-11-20 | Basf Se | Oxime ester photoinitiators |
CN102702073B (zh) | 2007-05-11 | 2015-06-10 | 巴斯夫欧洲公司 | 肟酯光引发剂 |
DE602008004757D1 (en) | 2007-05-11 | 2011-03-10 | Basf Se | Oximesther-fotoinitiatoren |
JP2009040762A (ja) | 2007-08-09 | 2009-02-26 | Ciba Holding Inc | オキシムエステル光開始剤 |
JP5553827B2 (ja) | 2008-06-06 | 2014-07-16 | ビーエーエスエフ ソシエタス・ヨーロピア | 光開始剤混合物 |
CN102203136B (zh) * | 2008-11-03 | 2013-11-13 | 巴斯夫欧洲公司 | 光敏引发剂混合物 |
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- 2009-05-27 WO PCT/EP2009/056397 patent/WO2009147031A2/en active Application Filing
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- 2009-05-27 CN CN200980130100.3A patent/CN102112438B/zh not_active Expired - Fee Related
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CN102112438A (zh) | 2011-06-29 |
KR20110015683A (ko) | 2011-02-16 |
EP2303833B1 (en) | 2013-10-16 |
US8507725B2 (en) | 2013-08-13 |
TWI466853B (zh) | 2015-01-01 |
US20110170209A1 (en) | 2011-07-14 |
TW201000434A (en) | 2010-01-01 |
WO2009147031A2 (en) | 2009-12-10 |
KR101626172B1 (ko) | 2016-05-31 |
EP2303833A2 (en) | 2011-04-06 |
JP2011525480A (ja) | 2011-09-22 |
WO2009147031A3 (en) | 2010-07-08 |
CN102112438B (zh) | 2014-07-23 |
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