NL1004597C2 - Boraat-co-initiatoren voor fotopolymerisatie. - Google Patents
Boraat-co-initiatoren voor fotopolymerisatie. Download PDFInfo
- Publication number
- NL1004597C2 NL1004597C2 NL1004597A NL1004597A NL1004597C2 NL 1004597 C2 NL1004597 C2 NL 1004597C2 NL 1004597 A NL1004597 A NL 1004597A NL 1004597 A NL1004597 A NL 1004597A NL 1004597 C2 NL1004597 C2 NL 1004597C2
- Authority
- NL
- Netherlands
- Prior art keywords
- alkyl
- phenyl
- substituted
- groups
- unsubstituted
- Prior art date
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- 239000003999 initiator Substances 0.000 title claims description 41
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 title claims description 15
- -1 anthracyl Chemical group 0.000 claims description 173
- 150000001875 compounds Chemical class 0.000 claims description 153
- 125000000217 alkyl group Chemical group 0.000 claims description 149
- 239000000203 mixture Substances 0.000 claims description 119
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 118
- 229910052736 halogen Inorganic materials 0.000 claims description 55
- 150000002367 halogens Chemical class 0.000 claims description 52
- 238000000576 coating method Methods 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 42
- CIDSGDKXNGKZIH-UHFFFAOYSA-N 4-N-(1-tert-butylsulfonyl-2,3-dihydroindol-6-yl)-2-N-[3-fluoro-4-(1-methylpiperidin-4-yl)phenyl]-5-methylpyrimidine-2,4-diamine Chemical compound C(C)(C)(C)S(=O)(=O)N1CCC2=CC=C(C=C12)NC1=NC(=NC=C1C)NC1=CC(=C(C=C1)C1CCN(CC1)C)F CIDSGDKXNGKZIH-UHFFFAOYSA-N 0.000 claims description 38
- 229910052740 iodine Inorganic materials 0.000 claims description 30
- 239000000463 material Substances 0.000 claims description 23
- 239000000758 substrate Substances 0.000 claims description 23
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 22
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 22
- 229920000642 polymer Polymers 0.000 claims description 21
- 239000000843 powder Substances 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 150000001768 cations Chemical class 0.000 claims description 14
- 102200059794 rs587777021 Human genes 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 12
- 239000000654 additive Substances 0.000 claims description 12
- 125000002091 cationic group Chemical group 0.000 claims description 12
- 238000007639 printing Methods 0.000 claims description 12
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical group C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 10
- 150000002500 ions Chemical class 0.000 claims description 10
- 239000006096 absorbing agent Substances 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 239000012965 benzophenone Substances 0.000 claims description 8
- 239000002131 composite material Substances 0.000 claims description 8
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 7
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 claims description 7
- 229910052796 boron Inorganic materials 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 230000007935 neutral effect Effects 0.000 claims description 7
- 230000003287 optical effect Effects 0.000 claims description 7
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 7
- 125000001725 pyrenyl group Chemical group 0.000 claims description 7
- 229910052723 transition metal Inorganic materials 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 125000000129 anionic group Chemical group 0.000 claims description 6
- 239000004922 lacquer Substances 0.000 claims description 6
- 238000007650 screen-printing Methods 0.000 claims description 6
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 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 5
- 239000000835 fiber Substances 0.000 claims description 5
- 239000012949 free radical photoinitiator Substances 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000005561 phenanthryl group Chemical group 0.000 claims description 5
- 125000005493 quinolyl group Chemical group 0.000 claims description 5
- 230000033458 reproduction Effects 0.000 claims description 5
- 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 claims description 5
- 238000012719 thermal polymerization Methods 0.000 claims description 5
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical class [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 claims description 5
- 229910019895 RuSi Inorganic materials 0.000 claims description 4
- 239000000853 adhesive Substances 0.000 claims description 4
- 230000001070 adhesive effect Effects 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 4
- 150000004056 anthraquinones Chemical class 0.000 claims description 4
- 150000008366 benzophenones Chemical class 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 4
- 239000003505 polymerization initiator Substances 0.000 claims description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 150000003624 transition metals Chemical class 0.000 claims description 4
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 claims description 4
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 3
- HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical compound NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 claims description 3
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
- 150000004010 onium ions Chemical class 0.000 claims description 3
- 239000003973 paint Substances 0.000 claims description 3
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 claims description 2
- ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical compound OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 claims description 2
- PESYEWKSBIWTAK-UHFFFAOYSA-N cyclopenta-1,3-diene;titanium(2+) Chemical compound [Ti+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 PESYEWKSBIWTAK-UHFFFAOYSA-N 0.000 claims description 2
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims description 2
- 230000001678 irradiating effect Effects 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 125000005537 sulfoxonium group Chemical group 0.000 claims description 2
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 claims 1
- GPTXWRGISTZRIO-UHFFFAOYSA-N chlorquinaldol Chemical compound ClC1=CC(Cl)=C(O)C2=NC(C)=CC=C21 GPTXWRGISTZRIO-UHFFFAOYSA-N 0.000 claims 1
- 229920002114 octoxynol-9 Polymers 0.000 claims 1
- 239000002966 varnish Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 description 49
- 150000001642 boronic acid derivatives Chemical class 0.000 description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 239000011248 coating agent Substances 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 238000002360 preparation method Methods 0.000 description 21
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 19
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 19
- 238000002844 melting Methods 0.000 description 18
- 230000008018 melting Effects 0.000 description 18
- 229920001577 copolymer Polymers 0.000 description 17
- 229910000085 borane Inorganic materials 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000004061 bleaching Methods 0.000 description 15
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 14
- 239000000370 acceptor Substances 0.000 description 14
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- 239000000178 monomer Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 12
- 238000001723 curing Methods 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 230000000007 visual effect Effects 0.000 description 12
- 239000010410 layer Substances 0.000 description 11
- 229920005862 polyol Polymers 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000008878 coupling Effects 0.000 description 9
- 238000010168 coupling process Methods 0.000 description 9
- 238000005859 coupling reaction Methods 0.000 description 9
- 238000011161 development Methods 0.000 description 9
- 150000003077 polyols Chemical class 0.000 description 9
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 229920000728 polyester Polymers 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 230000008901 benefit Effects 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 230000009257 reactivity Effects 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- 229910052749 magnesium Inorganic materials 0.000 description 6
- 150000002734 metacrylic acid derivatives Chemical class 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
- 230000008569 process Effects 0.000 description 6
- 230000035945 sensitivity Effects 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 6
- 125000004400 (C1-C12) alkyl group Chemical group 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 5
- 239000012964 benzotriazole Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 5
- 125000000332 coumarinyl group Chemical class O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000000600 sorbitol Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- 239000002023 wood Substances 0.000 description 5
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 4
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 235000001671 coumarin Nutrition 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 239000003365 glass fiber Substances 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000011976 maleic acid Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000007645 offset printing Methods 0.000 description 4
- 239000000123 paper Substances 0.000 description 4
- 150000004714 phosphonium salts Chemical class 0.000 description 4
- 238000000016 photochemical curing Methods 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- OARRHUQTFTUEOS-UHFFFAOYSA-N safranin Chemical compound [Cl-].C=12C=C(N)C(C)=CC2=NC2=CC(C)=C(N)C=C2[N+]=1C1=CC=CC=C1 OARRHUQTFTUEOS-UHFFFAOYSA-N 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 4
- 150000003573 thiols Chemical class 0.000 description 4
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 4
- 229920006337 unsaturated polyester resin Polymers 0.000 description 4
- 150000007964 xanthones Chemical class 0.000 description 4
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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
- 229910052711 selenium Inorganic materials 0.000 description 1
- GSMVXZUBBCEROW-UHFFFAOYSA-N selenopyran-1-ium Chemical compound C1=CC=[se+]C=C1 GSMVXZUBBCEROW-UHFFFAOYSA-N 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004528 spin coating Methods 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
- 238000003860 storage Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical class S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000003549 thiazolines Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- OKYDCMQQLGECPI-UHFFFAOYSA-N thiopyrylium Chemical compound C1=CC=[S+]C=C1 OKYDCMQQLGECPI-UHFFFAOYSA-N 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
- 150000003852 triazoles 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
- 229960001124 trientine Drugs 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- MDCWDBMBZLORER-UHFFFAOYSA-N triphenyl borate Chemical compound C=1C=CC=CC=1OB(OC=1C=CC=CC=1)OC1=CC=CC=C1 MDCWDBMBZLORER-UHFFFAOYSA-N 0.000 description 1
- RTMBXAOPKJNOGZ-UHFFFAOYSA-N tris(2-methylphenyl) borate Chemical compound CC1=CC=CC=C1OB(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C RTMBXAOPKJNOGZ-UHFFFAOYSA-N 0.000 description 1
- YFDAMRSZJLWUSQ-UHFFFAOYSA-N tris(2-methylphenyl)borane Chemical compound CC1=CC=CC=C1B(C=1C(=CC=CC=1)C)C1=CC=CC=C1C YFDAMRSZJLWUSQ-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
- DANLFSPBYIIYAA-UHFFFAOYSA-N tris(3,5-dichloro-2,4,6-trimethylphenyl)borane Chemical compound CC1=C(Cl)C(C)=C(Cl)C(C)=C1B(C=1C(=C(Cl)C(C)=C(Cl)C=1C)C)C1=C(C)C(Cl)=C(C)C(Cl)=C1C DANLFSPBYIIYAA-UHFFFAOYSA-N 0.000 description 1
- LPXPZPYLVNHPIG-UHFFFAOYSA-N tris(3-chloro-2,4,6-trimethylphenyl)borane Chemical compound CC1=C(Cl)C(C)=CC(C)=C1B(C=1C(=C(Cl)C(C)=CC=1C)C)C1=C(C)C=C(C)C(Cl)=C1C LPXPZPYLVNHPIG-UHFFFAOYSA-N 0.000 description 1
- NYSUZIDNILTGNF-UHFFFAOYSA-N tris(3-methylphenyl)borane Chemical compound CC1=CC=CC(B(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 NYSUZIDNILTGNF-UHFFFAOYSA-N 0.000 description 1
- LEIHCYASDULBKZ-UHFFFAOYSA-N tris(4-methylphenyl)borane Chemical compound C1=CC(C)=CC=C1B(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 LEIHCYASDULBKZ-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
- OINGBJKDRIWBKO-UHFFFAOYSA-N tris(trimethylsilylmethyl) borate Chemical compound C[Si](C)(C)COB(OC[Si](C)(C)C)OC[Si](C)(C)C OINGBJKDRIWBKO-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 150000003732 xanthenes Chemical class 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- 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
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
-
- 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
- G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
- Y10S430/115—Cationic or anionic
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
- Y10S430/117—Free radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polymerisation Methods In General (AREA)
- Materials For Photolithography (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Dental Preparations (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH334295 | 1995-11-24 | ||
CH334295 | 1995-11-24 |
Publications (2)
Publication Number | Publication Date |
---|---|
NL1004597A1 NL1004597A1 (nl) | 1997-05-27 |
NL1004597C2 true NL1004597C2 (nl) | 1998-01-07 |
Family
ID=4253902
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NL1004597A NL1004597C2 (nl) | 1995-11-24 | 1996-11-22 | Boraat-co-initiatoren voor fotopolymerisatie. |
Country Status (18)
Country | Link |
---|---|
US (2) | US5952152A (de) |
JP (1) | JPH09188685A (de) |
KR (1) | KR970028791A (de) |
CN (1) | CN1092199C (de) |
AT (1) | AT406775B (de) |
AU (1) | AU717137B2 (de) |
BE (1) | BE1010761A5 (de) |
BR (1) | BR9605697A (de) |
CA (1) | CA2191050A1 (de) |
DE (1) | DE19648313A1 (de) |
ES (1) | ES2126499B1 (de) |
FR (1) | FR2741622B1 (de) |
GB (1) | GB2307474B (de) |
IT (1) | IT1286500B1 (de) |
MX (1) | MX9605763A (de) |
NL (1) | NL1004597C2 (de) |
SG (1) | SG43445A1 (de) |
TW (1) | TW494123B (de) |
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EP0889362B1 (de) * | 1997-06-30 | 2003-08-27 | Showa Denko Kabushiki Kaisha | Fotopolymerisierbare Zusammensetzung und trockener Filmresist |
US6033829A (en) * | 1997-06-30 | 2000-03-07 | Showa Denko K.K. | Photopolymerizable composition and dry film resist |
FR2766490B1 (fr) * | 1997-07-23 | 1999-10-08 | Rhodia Chimie Sa | Nouveaux systemes amorceurs de polymerisation et/ou de reticulation comprenant un borate d'onium et une benzophenone |
US6218076B1 (en) * | 1997-08-26 | 2001-04-17 | Showa Denko K.K. | Stabilizer for organic borate salts and photosensitive composition containing the same |
TW455616B (en) * | 1997-11-03 | 2001-09-21 | Ciba Sc Holding Ag | New quinolinium dyes and borates, combinations thereof as photoinitiator compositions and photopolymerizable compositions comprising these photoinitiators |
EP0915136B1 (de) * | 1997-11-05 | 2004-01-21 | Showa Denko Kabushiki Kaisha | Photohärtbare Farbzusammensetzung für Strassenmarkierungen |
US6002044A (en) * | 1997-11-12 | 1999-12-14 | Showa Denko K.K. | Production method of borate compounds |
US6207726B1 (en) * | 1998-02-13 | 2001-03-27 | Showa Denko Kabushiki Kaisha | Photocurable prepreg composition and production method thereof |
JPH11316458A (ja) * | 1998-03-03 | 1999-11-16 | Fuji Photo Film Co Ltd | 感光性組成物 |
PT1114067E (pt) * | 1998-08-11 | 2003-03-31 | Rhodia Chimie Sa | Processo de polimerizacao e/ou de reticulacao sob um feixe de electroes e/ou de raios gama |
AU5620499A (en) * | 1998-08-21 | 2000-03-14 | Ciba Specialty Chemicals Holding Inc. | Photoactivatable bases containing nitrogen |
DE69916750T2 (de) * | 1998-11-17 | 2005-01-05 | Showa Denko K.K. | Photohärtbare Zusammensetzung |
SE9904080D0 (sv) * | 1998-12-03 | 1999-11-11 | Ciba Sc Holding Ag | Fotoinitiatorberedning |
DE60021449T2 (de) | 1999-02-26 | 2006-05-24 | Showa Denko K.K. | Photopolymerisationsinitiator für Farbfilter, Farbzusammensetzung und Farbfilter |
JP2000319283A (ja) * | 1999-03-08 | 2000-11-21 | Fuji Photo Film Co Ltd | ボレート化合物、それを含む光重合性組成物及び記録材料 |
SG78412A1 (en) | 1999-03-31 | 2001-02-20 | Ciba Sc Holding Ag | Oxime derivatives and the use thereof as latent acids |
US6479216B1 (en) * | 1999-09-15 | 2002-11-12 | Agfa-Gevaert | Method for obtaining a heat sensitive element by spray-coating |
EP1295179B1 (de) * | 2000-06-15 | 2013-05-22 | 3M Innovative Properties Company | Multiphotonaushärtung zur erzeugung von eingebetteten optischen bauteilen |
US7790353B2 (en) * | 2000-06-15 | 2010-09-07 | 3M Innovative Properties Company | Multidirectional photoreactive absorption method |
DE60139620D1 (de) * | 2000-06-15 | 2009-10-01 | 3M Innovative Properties Co | Methode und gerät zur erzielung wiederholter multiphotonabsorption |
WO2001096958A2 (en) * | 2000-06-15 | 2001-12-20 | 3M Innovative Properties Company | Process for producing microfluidic articles |
US6852766B1 (en) * | 2000-06-15 | 2005-02-08 | 3M Innovative Properties Company | Multiphoton photosensitization system |
DE60139624D1 (de) * | 2000-06-15 | 2009-10-01 | 3M Innovative Properties Co | Erzeugung eines mehrfarbenbildes mittels eines multiphoton photochemischen verfahren |
JP4188578B2 (ja) * | 2000-06-30 | 2008-11-26 | 富士フイルム株式会社 | 光重合性組成物並びにそれを用いた記録材料及び記録方法 |
US6864040B2 (en) | 2001-04-11 | 2005-03-08 | Kodak Polychrome Graphics Llc | Thermal initiator system using leuco dyes and polyhalogene compounds |
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US7592128B2 (en) | 2001-04-04 | 2009-09-22 | Eastman Kodak Company | On-press developable negative-working imageable elements |
US6893797B2 (en) | 2001-11-09 | 2005-05-17 | Kodak Polychrome Graphics Llc | High speed negative-working thermal printing plates |
US6846614B2 (en) | 2002-02-04 | 2005-01-25 | Kodak Polychrome Graphics Llc | On-press developable IR sensitive printing plates |
JP2002308922A (ja) * | 2001-04-12 | 2002-10-23 | Fuji Photo Film Co Ltd | 光重合性組成物並びにそれを用いた記録材料 |
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US6630555B2 (en) * | 2001-11-06 | 2003-10-07 | Lord Corporation | Internally blocked organoborate initiators and adhesives therefrom |
US20030155667A1 (en) * | 2002-12-12 | 2003-08-21 | Devoe Robert J | Method for making or adding structures to an article |
JP2004287138A (ja) * | 2003-03-24 | 2004-10-14 | Konica Minolta Holdings Inc | ホログラフィック記録用組成物、ホログラフィック記録メディア及びその記録方法 |
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- 1996-11-22 SG SG1996011342A patent/SG43445A1/en unknown
- 1996-11-22 AT AT0204096A patent/AT406775B/de not_active IP Right Cessation
- 1996-11-22 MX MX9605763A patent/MX9605763A/es unknown
- 1996-11-22 CA CA002191050A patent/CA2191050A1/en not_active Abandoned
- 1996-11-22 BE BE9600975A patent/BE1010761A5/fr not_active IP Right Cessation
- 1996-11-25 BR BR9605697A patent/BR9605697A/pt active Search and Examination
- 1996-11-25 JP JP8329208A patent/JPH09188685A/ja active Pending
- 1996-11-30 TW TW085114799A patent/TW494123B/zh not_active IP Right Cessation
-
1999
- 1999-05-19 US US09/314,391 patent/US6210863B1/en not_active Expired - Fee Related
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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US3567453A (en) * | 1967-12-26 | 1971-03-02 | Eastman Kodak Co | Light sensitive compositions for photoresists and lithography |
US3980654A (en) * | 1973-10-26 | 1976-09-14 | Eastman Kodak Company | Copper (II) complexes |
EP0468651A1 (de) * | 1990-07-03 | 1992-01-29 | The Dow Chemical Company | Additionspolymerisationskatalysator mit oxidativer Aktivität |
US5391661A (en) * | 1991-06-12 | 1995-02-21 | Idemitsu Kosan Co., Ltd. | Process for producing a styrenic polymer and a catalyst for use therein |
US5449583A (en) * | 1991-11-14 | 1995-09-12 | Showa Denko, K.K. | Method of making decolorizable toner |
Non-Patent Citations (1)
Title |
---|
BORDEN D G: "Review of light-sensitive tetraarylborates", PHOTOGRAPHIC SCIENCE AND ENGINEERING, vol. 16, no. 4, July 1972 (1972-07-01) - August 1972 (1972-08-01), pages 300 - 312, XP002041791 * |
Also Published As
Publication number | Publication date |
---|---|
BE1010761A5 (fr) | 1999-01-05 |
AU717137B2 (en) | 2000-03-16 |
TW494123B (en) | 2002-07-11 |
GB9624338D0 (en) | 1997-01-08 |
ES2126499B1 (es) | 1999-11-16 |
SG43445A1 (en) | 1997-10-17 |
AT406775B (de) | 2000-08-25 |
NL1004597A1 (nl) | 1997-05-27 |
FR2741622A1 (fr) | 1997-05-30 |
US5952152A (en) | 1999-09-14 |
CN1092199C (zh) | 2002-10-09 |
AU7179596A (en) | 1997-05-29 |
GB2307474A (en) | 1997-05-28 |
IT1286500B1 (it) | 1998-07-15 |
MX9605763A (es) | 1997-10-31 |
KR970028791A (ko) | 1997-06-24 |
ATA204096A (de) | 2000-01-15 |
BR9605697A (pt) | 1998-08-18 |
CA2191050A1 (en) | 1997-05-25 |
ITMI962438A0 (it) | 1996-11-22 |
DE19648313A1 (de) | 1997-05-28 |
ES2126499A1 (es) | 1999-03-16 |
CN1158854A (zh) | 1997-09-10 |
FR2741622B1 (fr) | 1998-12-04 |
JPH09188685A (ja) | 1997-07-22 |
ITMI962438A1 (it) | 1998-05-22 |
US6210863B1 (en) | 2001-04-03 |
GB2307474B (en) | 1999-12-15 |
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