DE69917261T2 - Photoinitiatoren und ihre Verwendungen - Google Patents
Photoinitiatoren und ihre Verwendungen Download PDFInfo
- Publication number
- DE69917261T2 DE69917261T2 DE69917261T DE69917261T DE69917261T2 DE 69917261 T2 DE69917261 T2 DE 69917261T2 DE 69917261 T DE69917261 T DE 69917261T DE 69917261 T DE69917261 T DE 69917261T DE 69917261 T2 DE69917261 T2 DE 69917261T2
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- substituted
- phenyl
- unsubstituted
- alkylene
- 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 - Lifetime
Links
- -1 biphenylyl Chemical group 0.000 claims description 132
- 125000000217 alkyl group Chemical group 0.000 claims description 119
- 239000000203 mixture Substances 0.000 claims description 72
- 239000000178 monomer Substances 0.000 claims description 65
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 65
- 125000002947 alkylene group Chemical group 0.000 claims description 56
- 239000001257 hydrogen Substances 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 229920001400 block copolymer Polymers 0.000 claims description 48
- 238000000576 coating method Methods 0.000 claims description 47
- 238000004519 manufacturing process Methods 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 38
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 238000005227 gel permeation chromatography Methods 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 24
- 239000003999 initiator Substances 0.000 claims description 24
- 150000002431 hydrogen Chemical group 0.000 claims description 22
- 229910052786 argon Inorganic materials 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 238000012546 transfer Methods 0.000 claims description 20
- 239000000463 material Substances 0.000 claims description 19
- 125000001931 aliphatic group Chemical group 0.000 claims description 18
- 239000000843 powder Substances 0.000 claims description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 13
- 239000000654 additive Substances 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 239000006185 dispersion Substances 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 238000007639 printing Methods 0.000 claims description 10
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 9
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 229920002120 photoresistant polymer Polymers 0.000 claims description 8
- 238000007650 screen-printing Methods 0.000 claims description 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000002131 composite material Substances 0.000 claims description 7
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 7
- 239000000049 pigment Substances 0.000 claims description 7
- 238000012719 thermal polymerization Methods 0.000 claims description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000001589 carboacyl group Chemical group 0.000 claims description 6
- 239000000835 fiber Substances 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 238000003384 imaging method Methods 0.000 claims description 6
- 229920003023 plastic Polymers 0.000 claims description 6
- 239000004033 plastic Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 239000008096 xylene Substances 0.000 claims description 6
- 150000008366 benzophenones Chemical class 0.000 claims description 5
- 125000002619 bicyclic group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000003973 paint Substances 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 239000000853 adhesive Substances 0.000 claims description 4
- 230000001070 adhesive effect Effects 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 239000000839 emulsion Substances 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 230000033458 reproduction Effects 0.000 claims description 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 claims description 3
- 229920001971 elastomer Polymers 0.000 claims description 3
- 238000011049 filling Methods 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 239000000976 ink Substances 0.000 claims description 3
- 239000012567 medical material Substances 0.000 claims description 3
- 239000003381 stabilizer Substances 0.000 claims description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
- 239000012986 chain transfer agent Substances 0.000 claims description 2
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 2
- 239000000806 elastomer Substances 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 230000001678 irradiating effect Effects 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000006839 xylylene group Chemical group 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims 1
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 84
- 150000002009 diols Chemical class 0.000 description 59
- 229940048053 acrylate Drugs 0.000 description 50
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 49
- 229920000642 polymer Polymers 0.000 description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 43
- 239000004793 Polystyrene Substances 0.000 description 36
- 229920002223 polystyrene Polymers 0.000 description 36
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 35
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 34
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 34
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 33
- 230000015572 biosynthetic process Effects 0.000 description 28
- 239000011248 coating agent Substances 0.000 description 28
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 26
- 239000005062 Polybutadiene Substances 0.000 description 25
- 229920002857 polybutadiene Polymers 0.000 description 25
- 238000003786 synthesis reaction Methods 0.000 description 25
- 239000004926 polymethyl methacrylate Substances 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 229920001577 copolymer Polymers 0.000 description 21
- 238000006116 polymerization reaction Methods 0.000 description 21
- 150000003254 radicals Chemical class 0.000 description 21
- 239000000758 substrate Substances 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 18
- 239000003708 ampul Substances 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- 229920002338 polyhydroxyethylmethacrylate Polymers 0.000 description 13
- 230000003287 optical effect Effects 0.000 description 12
- 229920001195 polyisoprene Polymers 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- 239000010410 layer Substances 0.000 description 11
- 229920005862 polyol Polymers 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 150000003077 polyols Chemical class 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 229920000728 polyester Polymers 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 8
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 7
- 229920002125 Sokalan® Polymers 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 6
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
- 239000011976 maleic acid Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000000016 photochemical curing Methods 0.000 description 6
- 229920000647 polyepoxide Polymers 0.000 description 6
- 229920002635 polyurethane Polymers 0.000 description 6
- 239000004814 polyurethane Substances 0.000 description 6
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- DWMSYQDOPYSCJR-UHFFFAOYSA-M 2-ethenyl-1-methylpyridin-1-ium;iodide Chemical compound [I-].C[N+]1=CC=CC=C1C=C DWMSYQDOPYSCJR-UHFFFAOYSA-M 0.000 description 5
- DYWCIVBBDWZOCL-UHFFFAOYSA-M 4-ethenyl-1-methylpyridin-1-ium;iodide Chemical compound [I-].C[N+]1=CC=C(C=C)C=C1 DYWCIVBBDWZOCL-UHFFFAOYSA-M 0.000 description 5
- 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 5
- 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 5
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 5
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- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 5
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 5
- 150000002019 disulfides Chemical class 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 5
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- 239000002023 wood Substances 0.000 description 5
- 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 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 4
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- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 4
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 4
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 4
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- 150000002576 ketones Chemical class 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical compound OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 description 4
- UJRDRFZCRQNLJM-UHFFFAOYSA-N methyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OC)=CC(N2N=C3C=CC=CC3=N2)=C1O UJRDRFZCRQNLJM-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- UKJARPDLRWBRAX-UHFFFAOYSA-N n,n'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine Chemical compound C1C(C)(C)NC(C)(C)CC1NCCCCCCNC1CC(C)(C)NC(C)(C)C1 UKJARPDLRWBRAX-UHFFFAOYSA-N 0.000 description 4
- KCAMXZBMXVIIQN-UHFFFAOYSA-N octan-3-yl 2-methylprop-2-enoate Chemical compound CCCCCC(CC)OC(=O)C(C)=C KCAMXZBMXVIIQN-UHFFFAOYSA-N 0.000 description 4
- 239000000123 paper Substances 0.000 description 4
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- 229920000075 poly(4-vinylpyridine) Polymers 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- SONHXMAHPHADTF-UHFFFAOYSA-M sodium;2-methylprop-2-enoate Chemical compound [Na+].CC(=C)C([O-])=O SONHXMAHPHADTF-UHFFFAOYSA-M 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000007669 thermal treatment Methods 0.000 description 4
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- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
- 229920006337 unsaturated polyester resin Polymers 0.000 description 4
- 229910052724 xenon Inorganic materials 0.000 description 4
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 4
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 3
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 3
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Classifications
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- 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
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
- A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/45—Anti-settling agents
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/65—Additives macromolecular
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Physics & Mathematics (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Plastic & Reconstructive Surgery (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Veterinary Medicine (AREA)
- Polymerisation Methods In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98810501 | 1998-05-29 | ||
| EP98810501 | 1998-05-29 | ||
| PCT/EP1999/003458 WO1999062961A1 (en) | 1998-05-29 | 1999-05-20 | Novel photoinitiators and their applications |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69917261D1 DE69917261D1 (de) | 2004-06-17 |
| DE69917261T2 true DE69917261T2 (de) | 2004-09-09 |
Family
ID=8236118
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69917261T Expired - Lifetime DE69917261T2 (de) | 1998-05-29 | 1999-05-20 | Photoinitiatoren und ihre Verwendungen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6458864B1 (enExample) |
| EP (1) | EP1086145B1 (enExample) |
| JP (1) | JP4975211B2 (enExample) |
| AU (1) | AU4363999A (enExample) |
| DE (1) | DE69917261T2 (enExample) |
| WO (1) | WO1999062961A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1333790A (zh) | 1998-12-31 | 2002-01-30 | 西巴特殊化学品控股有限公司 | 含atrp聚合物的颜料组合物 |
| EP1177182B1 (en) | 1999-05-10 | 2006-11-29 | Ciba SC Holding AG | Novel photoinitiators and their applications |
| DE10039212A1 (de) * | 2000-08-11 | 2002-02-21 | Tesa Ag | Verfahren zur Herstellung haftklebriger Polyacrylate unter Verwendung mercaptofunktionalisierter Photoinitiatoren |
| DE10149084A1 (de) * | 2001-10-05 | 2003-06-18 | Tesa Ag | UV-vernetzbare Acrylathaftschmelzhaftkleber mit enger Molekulargewichtsverteilung |
| US6908952B2 (en) * | 2003-03-21 | 2005-06-21 | 3M Innovative Properties Company | Ring-opened azlactone photoiniferters for radical polymerization |
| JP5159097B2 (ja) * | 2006-09-22 | 2013-03-06 | 富士フイルム株式会社 | インク組成物、インクジェット記録方法及び印刷物 |
| WO2008070737A1 (en) * | 2006-12-05 | 2008-06-12 | University Of Southern Mississippi | Benzophenone/thioxanthone derivatives and their use in photopolymerizable compositions |
| JP5136035B2 (ja) * | 2007-12-11 | 2013-02-06 | コニカミノルタホールディングス株式会社 | インクジェットインク及びインクジェット記録方法 |
| JP5441574B2 (ja) * | 2009-09-08 | 2014-03-12 | 富士フイルム株式会社 | 水性インク組成物、インクセット、およびインクジェット画像形成方法 |
| JP5955832B2 (ja) * | 2010-03-22 | 2016-07-20 | ヘンケル アイピー アンド ホールディング ゲゼルシャフト ミット ベシュレンクテル ハフツング | マクロ光開始剤およびそれらの硬化性組成物 |
| JP5455818B2 (ja) * | 2010-06-29 | 2014-03-26 | 富士フイルム株式会社 | インク組成物、インクセット及び画像形成方法 |
| AT514594B1 (de) | 2013-09-06 | 2015-02-15 | Durst Phototech Digital Tech | Photoinitiator |
| WO2016017537A1 (ja) * | 2014-08-01 | 2016-02-04 | 株式会社Adeka | 新規重合開始剤及び該重合開始剤を含有するラジカル重合性組成物 |
| TWI677492B (zh) * | 2018-07-17 | 2019-11-21 | 奇鈦科技股份有限公司 | 液態光引發化合物及其應用 |
| CN109988262B (zh) * | 2019-04-03 | 2020-07-14 | 北京化工大学 | 一种聚合大分子光引发剂及其制备方法 |
| CN110003365B (zh) * | 2019-04-03 | 2020-06-09 | 北京化工大学 | 一种大分子光引发剂及其制备方法 |
| CN109988268B (zh) * | 2019-04-03 | 2020-08-04 | 北京化工大学 | 一种共聚合大分子光引发剂及其制备方法 |
| CN109970727B (zh) * | 2019-04-03 | 2021-04-06 | 北京化工大学 | 一种长波长可聚合光引发剂及其制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0088050B1 (de) * | 1982-02-26 | 1986-09-03 | Ciba-Geigy Ag | Photohärtbare gefärbte Massen |
| DE3738567A1 (de) * | 1987-03-12 | 1988-09-22 | Merck Patent Gmbh | Coreaktive fotoinitiatoren |
| US5314962A (en) * | 1987-04-07 | 1994-05-24 | Mitsubishi Petrochemical Company Limited | ABA type block copolymers |
| US5190989A (en) * | 1987-06-23 | 1993-03-02 | Mitsubishi Petrochemical Company Limited | Hydrophilic group-containing AB-type block copolymer |
| DE3816304A1 (de) * | 1988-05-13 | 1989-11-23 | Merck Patent Gmbh | Fotoinitiator-copolymere |
| US5057619A (en) * | 1989-08-14 | 1991-10-15 | Minnesota Mining And Manufacturing Co. | Siloxane iniferter compounds, block copolymers made therewith and a method of making the block copolymers |
| JP2845973B2 (ja) * | 1989-09-04 | 1999-01-13 | 三菱化学株式会社 | ジチオカーバメート基含有ポリエステル |
| JP3112702B2 (ja) * | 1991-06-13 | 2000-11-27 | 積水化学工業株式会社 | ポリマー型光重合開始剤、その製法および使用法 |
| JP3346486B2 (ja) * | 1993-03-29 | 2002-11-18 | 大日本インキ化学工業株式会社 | 含フッ素ブロック共重合体の製造方法 |
| US5942555A (en) * | 1996-03-21 | 1999-08-24 | Surmodics, Inc. | Photoactivatable chain transfer agents and semi-telechelic photoactivatable polymers prepared therefrom |
| JP3730719B2 (ja) * | 1996-08-12 | 2006-01-05 | 積水化学工業株式会社 | ブロック共重合体の製造方法 |
| TW452575B (en) | 1996-12-06 | 2001-09-01 | Ciba Sc Holding Ag | New Α-aminoacetophenone photoinitiators and photopolymerizable compositions comprising these photoinitiators |
-
1999
- 1999-05-20 DE DE69917261T patent/DE69917261T2/de not_active Expired - Lifetime
- 1999-05-20 WO PCT/EP1999/003458 patent/WO1999062961A1/en not_active Ceased
- 1999-05-20 JP JP2000552170A patent/JP4975211B2/ja not_active Expired - Fee Related
- 1999-05-20 US US09/701,457 patent/US6458864B1/en not_active Expired - Fee Related
- 1999-05-20 EP EP99926340A patent/EP1086145B1/en not_active Expired - Lifetime
- 1999-05-20 AU AU43639/99A patent/AU4363999A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US6458864B1 (en) | 2002-10-01 |
| JP4975211B2 (ja) | 2012-07-11 |
| JP2002517522A (ja) | 2002-06-18 |
| WO1999062961A1 (en) | 1999-12-09 |
| DE69917261D1 (de) | 2004-06-17 |
| AU4363999A (en) | 1999-12-20 |
| EP1086145B1 (en) | 2004-05-12 |
| EP1086145A1 (en) | 2001-03-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8328 | Change in the person/name/address of the agent |
Representative=s name: PFENNING MEINIG & PARTNER GBR, 80339 MUENCHEN |
|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: CIBA HOLDING INC., BASEL, CH |
|
| 8328 | Change in the person/name/address of the agent |
Representative=s name: MAIWALD PATENTANWALTSGESELLSCHAFT MBH, 80335 MUENC |