TWI404699B - 鹽起始劑 - Google Patents
鹽起始劑 Download PDFInfo
- Publication number
- TWI404699B TWI404699B TW096112895A TW96112895A TWI404699B TW I404699 B TWI404699 B TW I404699B TW 096112895 A TW096112895 A TW 096112895A TW 96112895 A TW96112895 A TW 96112895A TW I404699 B TWI404699 B TW I404699B
- Authority
- TW
- Taiwan
- Prior art keywords
- acid
- group
- compound
- substituted
- alkyl
- Prior art date
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- 239000003999 initiator Substances 0.000 title description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 180
- 239000001257 hydrogen Substances 0.000 claims abstract description 102
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 102
- 239000002253 acid Substances 0.000 claims abstract description 68
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 56
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 55
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 150000001449 anionic compounds Chemical class 0.000 claims abstract description 15
- 150000002891 organic anions Chemical class 0.000 claims abstract description 15
- -1 R 1 Chemical class 0.000 claims description 178
- 239000000203 mixture Substances 0.000 claims description 109
- 125000000217 alkyl group Chemical group 0.000 claims description 105
- 150000002431 hydrogen Chemical class 0.000 claims description 76
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 54
- 238000000576 coating method Methods 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 49
- 229910052736 halogen Inorganic materials 0.000 claims description 48
- 150000002367 halogens Chemical class 0.000 claims description 48
- 125000003118 aryl group Chemical group 0.000 claims description 35
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 33
- 238000002360 preparation method Methods 0.000 claims description 33
- 229920005989 resin Polymers 0.000 claims description 33
- 239000011347 resin Substances 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 230000005855 radiation Effects 0.000 claims description 28
- 238000004519 manufacturing process Methods 0.000 claims description 27
- 239000003054 catalyst Substances 0.000 claims description 26
- 239000000463 material Substances 0.000 claims description 21
- 229920002554 vinyl polymer Polymers 0.000 claims description 21
- 150000001450 anions Chemical class 0.000 claims description 19
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 18
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 239000000758 substrate Substances 0.000 claims description 17
- 238000007639 printing Methods 0.000 claims description 16
- 239000000654 additive Substances 0.000 claims description 14
- 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 claims description 12
- 239000011230 binding agent Substances 0.000 claims description 11
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 11
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 11
- 239000008199 coating composition Substances 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 7
- 230000009471 action Effects 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 150000001767 cationic compounds Chemical class 0.000 claims description 7
- 150000002892 organic cations Chemical class 0.000 claims description 7
- 125000006755 (C2-C20) alkyl group Chemical group 0.000 claims description 6
- 125000002091 cationic group Chemical group 0.000 claims description 6
- 239000000945 filler Substances 0.000 claims description 5
- 229910017008 AsF 6 Inorganic materials 0.000 claims description 4
- 229910018286 SbF 6 Inorganic materials 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
- 230000000181 anti-adherent effect Effects 0.000 claims description 4
- 239000002243 precursor Substances 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 3
- 125000005647 linker group Chemical group 0.000 abstract description 8
- 229920000180 alkyd Polymers 0.000 description 60
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 50
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- 238000006243 chemical reaction Methods 0.000 description 41
- 239000011248 coating agent Substances 0.000 description 40
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 35
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 32
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 31
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 27
- 229920001577 copolymer Polymers 0.000 description 26
- 229920000642 polymer Polymers 0.000 description 25
- 238000005160 1H NMR spectroscopy Methods 0.000 description 24
- 239000000178 monomer Substances 0.000 description 24
- 238000009472 formulation Methods 0.000 description 23
- 239000004593 Epoxy Substances 0.000 description 22
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Substances CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 22
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 21
- 229920005862 polyol Polymers 0.000 description 21
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 19
- 229910002091 carbon monoxide Inorganic materials 0.000 description 19
- 239000012948 isocyanate Substances 0.000 description 19
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 19
- 239000000126 substance Substances 0.000 description 19
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 229960000834 vinyl ether Drugs 0.000 description 18
- 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 17
- 125000001931 aliphatic group Chemical group 0.000 description 17
- 229920002120 photoresistant polymer Polymers 0.000 description 17
- 239000000049 pigment Substances 0.000 description 17
- 150000003254 radicals Chemical class 0.000 description 17
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 16
- 150000002513 isocyanates Chemical class 0.000 description 16
- 150000003077 polyols Chemical class 0.000 description 16
- 239000004814 polyurethane Substances 0.000 description 16
- 229920002635 polyurethane Polymers 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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 15
- 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 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 15
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 15
- 125000000524 functional group Chemical group 0.000 description 15
- 229920000728 polyester Polymers 0.000 description 15
- 239000000600 sorbitol Substances 0.000 description 15
- 125000003277 amino group Chemical group 0.000 description 14
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 14
- 229920000647 polyepoxide Polymers 0.000 description 14
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 13
- 229920000877 Melamine resin Polymers 0.000 description 13
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- 229920001228 polyisocyanate Polymers 0.000 description 12
- 239000005056 polyisocyanate Substances 0.000 description 12
- 239000004925 Acrylic resin Substances 0.000 description 11
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 11
- 150000001241 acetals Chemical class 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 11
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 11
- 125000003700 epoxy group Chemical group 0.000 description 11
- 239000003607 modifier Substances 0.000 description 11
- DJNIFZYQFLFGDT-UHFFFAOYSA-N 1-(4-phenoxyphenyl)ethanone Chemical compound C1=CC(C(=O)C)=CC=C1OC1=CC=CC=C1 DJNIFZYQFLFGDT-UHFFFAOYSA-N 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 10
- 239000000976 ink Substances 0.000 description 10
- 229920000570 polyether Polymers 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 9
- 239000000853 adhesive Substances 0.000 description 9
- 230000001070 adhesive effect Effects 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- 150000001735 carboxylic acids Chemical class 0.000 description 9
- 150000002009 diols Chemical class 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 229920000178 Acrylic resin Polymers 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
- 150000002118 epoxides Chemical class 0.000 description 8
- 125000004185 ester group Chemical group 0.000 description 8
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000005011 phenolic resin Substances 0.000 description 8
- 229920000058 polyacrylate Polymers 0.000 description 8
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000003381 stabilizer Substances 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 7
- 239000004721 Polyphenylene oxide Substances 0.000 description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 7
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 7
- 239000012952 cationic photoinitiator Substances 0.000 description 7
- 238000001723 curing Methods 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 7
- 239000000975 dye Substances 0.000 description 7
- 239000003822 epoxy resin Substances 0.000 description 7
- 150000002170 ethers Chemical class 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 235000011187 glycerol Nutrition 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 7
- 239000011976 maleic acid Substances 0.000 description 7
- 229920001568 phenolic resin Polymers 0.000 description 7
- 229920000768 polyamine Polymers 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 238000005809 transesterification reaction Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- 229940052303 ethers for general anesthesia Drugs 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 6
- 230000000269 nucleophilic effect Effects 0.000 description 6
- 150000004714 phosphonium salts Chemical class 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- 229920001225 polyester resin Polymers 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 239000000370 acceptor Substances 0.000 description 5
- 238000007259 addition reaction Methods 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 5
- 229940106691 bisphenol a Drugs 0.000 description 5
- 238000006555 catalytic reaction Methods 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 239000004645 polyester resin Substances 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 4
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 4
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 4
- LSTZTHCEEPHCNQ-UHFFFAOYSA-N 3-(2,5-dioxabicyclo[2.1.0]pentan-3-yloxy)-2,5-dioxabicyclo[2.1.0]pentane Chemical compound C1(C2C(O2)O1)OC1C2C(O2)O1 LSTZTHCEEPHCNQ-UHFFFAOYSA-N 0.000 description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 241000208340 Araliaceae Species 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 4
- 235000003140 Panax quinquefolius Nutrition 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 4
- 125000005228 aryl sulfonate group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
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- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003527 tetrahydropyrans Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical class C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 229940029273 trichloroacetaldehyde Drugs 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-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
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- RSJKGSCJYJTIGS-BJUDXGSMSA-N undecane Chemical compound CCCCCCCCCC[11CH3] RSJKGSCJYJTIGS-BJUDXGSMSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- INRGAWUQFOBNKL-UHFFFAOYSA-N {4-[(Vinyloxy)methyl]cyclohexyl}methanol Chemical compound OCC1CCC(COC=C)CC1 INRGAWUQFOBNKL-UHFFFAOYSA-N 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/12—Sulfonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B61/00—Other general methods
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
-
- 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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/03—Powdery paints
- C09D5/033—Powdery paints characterised by the additives
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/08—Anti-corrosive paints
-
- 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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Physics & Mathematics (AREA)
- Paints Or Removers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerisation Methods In General (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polyethers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06112602 | 2006-04-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200804260A TW200804260A (en) | 2008-01-16 |
| TWI404699B true TWI404699B (zh) | 2013-08-11 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW096112895A TWI404699B (zh) | 2006-04-13 | 2007-04-12 | 鹽起始劑 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8067643B2 (enExample) |
| EP (1) | EP2007834B1 (enExample) |
| JP (1) | JP5313873B2 (enExample) |
| KR (1) | KR101389057B1 (enExample) |
| CN (1) | CN101466804B (enExample) |
| TW (1) | TWI404699B (enExample) |
| WO (1) | WO2007118794A1 (enExample) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP5290183B2 (ja) | 2006-10-04 | 2013-09-18 | チバ ホールディング インコーポレーテッド | スルホニウム塩光開始剤 |
| JP5538229B2 (ja) | 2007-10-10 | 2014-07-02 | ビーエーエスエフ ソシエタス・ヨーロピア | スルホニウム塩開始剤 |
| CN101952269B (zh) | 2007-10-10 | 2014-06-25 | 巴斯夫欧洲公司 | 锍盐引发剂 |
| US8512934B2 (en) | 2007-10-10 | 2013-08-20 | Basf Se | Sulphonium salt initiators |
| KR20110025211A (ko) * | 2008-06-12 | 2011-03-09 | 바스프 에스이 | 술포늄 유도체 및 잠재성 산으로서의 그의 용도 |
| JP5247396B2 (ja) * | 2008-07-02 | 2013-07-24 | 日本化薬株式会社 | Mems用感光性樹脂組成物及びその硬化物 |
| EP2349993B1 (en) * | 2008-10-20 | 2012-12-12 | Basf Se | Sulfonium derivatives and the use therof as latent acids |
| WO2010071956A1 (en) | 2008-12-22 | 2010-07-01 | Canadian Bank Note Company, Limited | Improved printing of tactile marks for the visually impaired |
| EP2199856B1 (en) | 2008-12-18 | 2013-08-07 | Agfa Graphics N.V. | Cationic radiation curable compositions |
| GB0823282D0 (en) * | 2008-12-20 | 2009-01-28 | Univ Strathclyde | Dose responsive UV indicator |
| US8617787B2 (en) * | 2009-02-20 | 2013-12-31 | San-Apro, Ltd. | Sulfonium salt, photo-acid generator, and photosensitive resin composition |
| EP2438122A1 (en) * | 2009-06-02 | 2012-04-11 | Massachusetts Institute of Technology | Coatings |
| JP5387181B2 (ja) * | 2009-07-08 | 2014-01-15 | 信越化学工業株式会社 | スルホニウム塩、レジスト材料及びパターン形成方法 |
| KR101821426B1 (ko) * | 2009-12-17 | 2018-01-23 | 디에스엠 아이피 어셋츠 비.브이. | 기판-기재 적층식 제작 공정 |
| CN102781911B (zh) | 2010-02-24 | 2015-07-22 | 巴斯夫欧洲公司 | 潜酸及其用途 |
| TWI523882B (zh) | 2010-07-14 | 2016-03-01 | 日本化藥股份有限公司 | 感光性樹脂組成物及其硬化物 |
| US8394575B2 (en) * | 2010-09-30 | 2013-03-12 | Lexmark International, Inc. | Formulations for environmentally friendly photoresist film layers |
| KR20140007797A (ko) * | 2010-10-07 | 2014-01-20 | 도오꾜오까고오교 가부시끼가이샤 | 가이드 패턴 형성용 네거티브형 현상용 레지스트 조성물, 가이드 패턴 형성 방법, 블록 코폴리머를 포함하는 층의 패턴 형성 방법 |
| JP5691987B2 (ja) * | 2010-10-13 | 2015-04-01 | 信越化学工業株式会社 | 光硬化性樹脂組成物、そのドライフィルム、パターン形成方法及び電気・電子部品保護用皮膜 |
| JP5749631B2 (ja) * | 2010-12-07 | 2015-07-15 | 東京応化工業株式会社 | 厚膜用化学増幅型ポジ型ホトレジスト組成物及び厚膜レジストパターンの製造方法 |
| US8816211B2 (en) * | 2011-02-14 | 2014-08-26 | Eastman Kodak Company | Articles with photocurable and photocured compositions |
| GB201223064D0 (en) * | 2012-12-20 | 2013-02-06 | Rainbow Technology Systems Ltd | Curable coatings for photoimaging |
| CN107207456B (zh) | 2015-02-02 | 2021-05-04 | 巴斯夫欧洲公司 | 潜酸及其用途 |
| US10604659B2 (en) | 2015-06-08 | 2020-03-31 | Dsm Ip Assets B.V. | Liquid, hybrid UV/VIS radiation curable resin compositions for additive fabrication |
| JP6880416B2 (ja) | 2015-10-01 | 2021-06-02 | ディーエスエム アイピー アセッツ ビー.ブイ.Dsm Ip Assets B.V. | 付加造形用液状ハイブリッドUV/vis線硬化性樹脂組成物 |
| JP2018536731A (ja) | 2015-11-17 | 2018-12-13 | ディーエスエム アイピー アセッツ ビー.ブイ.Dsm Ip Assets B.V. | 改善された付加造形用アンチモンフリー放射線硬化性組成物およびインベストメント鋳造プロセスにおけるその用途 |
| EP3492476A4 (en) * | 2016-07-28 | 2020-03-18 | San-Apro Ltd. | SULFONIUM SALT, HEAT OR PHOTO-ACID GENERATOR, THERMOSETTING OR PHOTOSETTING COMPOSITION, AND CORRESPONDING HARDENED PRODUCT |
| CN107698477B (zh) | 2016-08-08 | 2020-05-12 | 常州强力电子新材料股份有限公司 | 一种新型阳离子型光引发剂及其制备方法和应用 |
| CN109843853B (zh) * | 2016-10-17 | 2022-09-20 | 东洋合成工业株式会社 | 组合物和使用该组合物的设备的制造方法 |
| CN109135392B (zh) * | 2017-06-15 | 2021-11-02 | 常州强力电子新材料股份有限公司 | 一种双硫鎓盐光引发剂 |
| 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 |
| CN109456242B (zh) | 2017-09-06 | 2021-02-12 | 常州强力电子新材料股份有限公司 | 硫鎓盐光引发剂、其制备方法、包含其的光固化组合物及其应用 |
| CN110922346A (zh) * | 2019-11-12 | 2020-03-27 | 上海鑫响实业有限公司 | 一种三(4-乙酰联苯硫醚)硫醚鎓六氟磷酸盐及其合成方法 |
| EP4122915A4 (en) | 2020-03-17 | 2023-09-06 | San-Apro Ltd. | Sulfonium salt, photoacid generator, curable composition, and resist composition |
| JP7702796B2 (ja) * | 2020-04-22 | 2025-07-04 | 住友化学株式会社 | カルボン酸塩、カルボン酸発生剤、レジスト組成物及びレジストパターンの製造方法 |
| JP7716899B2 (ja) * | 2020-07-16 | 2025-08-01 | 住友化学株式会社 | 塩、酸発生剤、レジスト組成物及びレジストパターンの製造方法 |
| JP7716900B2 (ja) * | 2020-07-16 | 2025-08-01 | 住友化学株式会社 | カルボン酸塩、カルボン酸発生剤、レジスト組成物及びレジストパターンの製造方法 |
| JP7758495B2 (ja) * | 2020-08-03 | 2025-10-22 | 住友化学株式会社 | 酸発生剤、樹脂、レジスト組成物及びレジストパターンの製造方法 |
| JP7713327B2 (ja) * | 2020-08-03 | 2025-07-25 | 住友化学株式会社 | カルボン酸塩、カルボン酸発生剤、樹脂、レジスト組成物及びレジストパターンの製造方法 |
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- 2007-04-04 US US12/226,116 patent/US8067643B2/en active Active
- 2007-04-04 KR KR1020087027838A patent/KR101389057B1/ko active Active
- 2007-04-04 WO PCT/EP2007/053280 patent/WO2007118794A1/en not_active Ceased
- 2007-04-04 JP JP2009504692A patent/JP5313873B2/ja active Active
- 2007-04-04 CN CN2007800216146A patent/CN101466804B/zh active Active
- 2007-04-04 EP EP07727751.5A patent/EP2007834B1/en active Active
- 2007-04-12 TW TW096112895A patent/TWI404699B/zh active
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1036789A1 (en) * | 1997-12-04 | 2000-09-20 | Asahi Denka Kogyo Kabushiki Kaisha | Novel aromatic sulfonium compounds, photoacid generators comprising the same, photopolymerizable compositions containing the same, stereolithographic resin compositions, and stereolithographic process |
| EP1557413A1 (en) * | 2002-09-25 | 2005-07-27 | Asahi Denka Co., Ltd. | Novel aromatic sulfonium salt compound, photo-acid generator comprising the same and photopolymerizable composition containing the same, resin composition for optical three-dimensional shaping, and method of optically forming three-dimensional shape |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2007834A1 (en) | 2008-12-31 |
| US8067643B2 (en) | 2011-11-29 |
| EP2007834B1 (en) | 2015-11-04 |
| CN101466804A (zh) | 2009-06-24 |
| US20090197987A1 (en) | 2009-08-06 |
| JP5313873B2 (ja) | 2013-10-09 |
| CN101466804B (zh) | 2012-02-22 |
| JP2009533377A (ja) | 2009-09-17 |
| KR20080112377A (ko) | 2008-12-24 |
| WO2007118794A1 (en) | 2007-10-25 |
| TW200804260A (en) | 2008-01-16 |
| KR101389057B1 (ko) | 2014-05-13 |
| WO2007118794B1 (en) | 2008-01-03 |
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