KR101389057B1 - 설포늄 염 개시제 - Google Patents
설포늄 염 개시제 Download PDFInfo
- Publication number
- KR101389057B1 KR101389057B1 KR1020087027838A KR20087027838A KR101389057B1 KR 101389057 B1 KR101389057 B1 KR 101389057B1 KR 1020087027838 A KR1020087027838 A KR 1020087027838A KR 20087027838 A KR20087027838 A KR 20087027838A KR 101389057 B1 KR101389057 B1 KR 101389057B1
- Authority
- KR
- South Korea
- Prior art keywords
- substituted
- alkyl
- acid
- hydrogen
- compound
- 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.)
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- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 title description 10
- 239000003999 initiator Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 163
- 239000000203 mixture Substances 0.000 claims abstract description 116
- 239000001257 hydrogen Substances 0.000 claims abstract description 104
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 104
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 82
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 62
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 62
- 239000002253 acid Substances 0.000 claims abstract description 41
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 230000005855 radiation Effects 0.000 claims abstract description 19
- 239000000463 material Substances 0.000 claims abstract description 16
- 150000001449 anionic compounds Chemical class 0.000 claims abstract description 15
- 150000002891 organic anions Chemical class 0.000 claims abstract description 15
- 239000008199 coating composition Substances 0.000 claims abstract description 10
- -1 o- phenylene Chemical group 0.000 claims description 146
- 125000000217 alkyl group Chemical group 0.000 claims description 102
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 63
- 238000000034 method Methods 0.000 claims description 59
- 125000003118 aryl group Chemical group 0.000 claims description 57
- 238000004519 manufacturing process Methods 0.000 claims description 53
- 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 claims description 50
- 229910052736 halogen Inorganic materials 0.000 claims description 49
- 150000002367 halogens Chemical class 0.000 claims description 49
- 238000000576 coating method Methods 0.000 claims description 48
- 229920005989 resin Polymers 0.000 claims description 36
- 239000011347 resin Substances 0.000 claims description 36
- 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
- 125000003342 alkenyl group Chemical group 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 229920002554 vinyl polymer Polymers 0.000 claims description 27
- 239000003054 catalyst Substances 0.000 claims description 25
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 24
- 239000011248 coating agent Substances 0.000 claims description 20
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 20
- 230000008569 process Effects 0.000 claims description 17
- 239000000758 substrate Substances 0.000 claims description 17
- 238000007639 printing Methods 0.000 claims description 16
- 150000001450 anions Chemical class 0.000 claims description 14
- 239000000654 additive Substances 0.000 claims description 13
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 12
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 12
- 125000002091 cationic group Chemical group 0.000 claims description 12
- 239000000853 adhesive Substances 0.000 claims description 9
- 230000001070 adhesive effect Effects 0.000 claims description 9
- 230000009471 action Effects 0.000 claims description 8
- 150000001767 cationic compounds Chemical class 0.000 claims description 8
- 238000004132 cross linking Methods 0.000 claims description 8
- 238000010894 electron beam technology Methods 0.000 claims description 8
- 150000002892 organic cations Chemical class 0.000 claims description 8
- 230000000996 additive effect Effects 0.000 claims description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 7
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 101100203600 Caenorhabditis elegans sor-1 gene Proteins 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
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000002131 composite material Substances 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 3
- 230000000181 anti-adherent effect Effects 0.000 claims description 2
- 230000003373 anti-fouling effect Effects 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
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- 239000011350 dental composite resin Substances 0.000 claims 2
- 238000007641 inkjet printing Methods 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 abstract description 7
- 125000005647 linker group Chemical group 0.000 abstract description 6
- 229920000180 alkyd Polymers 0.000 description 62
- 238000006243 chemical reaction Methods 0.000 description 42
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 27
- 229920000642 polymer Polymers 0.000 description 27
- 238000009472 formulation Methods 0.000 description 26
- 229920001577 copolymer Polymers 0.000 description 25
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 24
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 24
- 239000000178 monomer Substances 0.000 description 22
- 229920005862 polyol Polymers 0.000 description 22
- 239000002904 solvent Substances 0.000 description 22
- 239000004593 Epoxy Substances 0.000 description 20
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 18
- 125000001931 aliphatic group Chemical group 0.000 description 18
- 150000003077 polyols Chemical class 0.000 description 17
- 229920000877 Melamine resin Polymers 0.000 description 16
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 16
- 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
- 229920002120 photoresistant polymer Polymers 0.000 description 16
- 229920000728 polyester Polymers 0.000 description 16
- 239000004814 polyurethane Substances 0.000 description 16
- 229920002635 polyurethane Polymers 0.000 description 16
- 239000000126 substance Substances 0.000 description 16
- 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 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
- 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
- 229920000647 polyepoxide Polymers 0.000 description 15
- 239000000600 sorbitol Substances 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 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 14
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 14
- 125000000524 functional group Chemical group 0.000 description 14
- 239000012948 isocyanate Substances 0.000 description 14
- 239000000049 pigment Substances 0.000 description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 229960000834 vinyl ether Drugs 0.000 description 13
- 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 12
- 239000011230 binding agent Substances 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 238000001723 curing Methods 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 150000001241 acetals Chemical class 0.000 description 10
- 125000002947 alkylene group Chemical group 0.000 description 10
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 229920000570 polyether Polymers 0.000 description 10
- 239000005056 polyisocyanate Substances 0.000 description 10
- 229920001228 polyisocyanate Polymers 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 9
- 125000003700 epoxy group Chemical group 0.000 description 9
- 125000004185 ester group Chemical group 0.000 description 9
- 239000000976 ink Substances 0.000 description 9
- 150000002513 isocyanates Chemical class 0.000 description 9
- 239000003607 modifier Substances 0.000 description 9
- 229920000058 polyacrylate Polymers 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- 125000003277 amino group Chemical group 0.000 description 8
- 150000001735 carboxylic acids Chemical class 0.000 description 8
- 239000000975 dye Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 7
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 7
- 239000004721 Polyphenylene oxide Substances 0.000 description 7
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 7
- 150000008064 anhydrides Chemical class 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 239000002274 desiccant Substances 0.000 description 7
- 150000002009 diols Chemical class 0.000 description 7
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 7
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000003381 stabilizer Substances 0.000 description 7
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- 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 6
- 229920000178 Acrylic resin Polymers 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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- 238000007259 addition reaction Methods 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
- 150000001412 amines Chemical class 0.000 description 6
- 239000012965 benzophenone Substances 0.000 description 6
- 239000012952 cationic photoinitiator Substances 0.000 description 6
- 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 6
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 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
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- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 6
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 6
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- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-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
- 239000004925 Acrylic resin Substances 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 5
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- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 5
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 5
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
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- 230000003197 catalytic effect Effects 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
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- 229910000679 solder Inorganic materials 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000008117 stearic acid Substances 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
- 150000003440 styrenes Chemical class 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 238000006351 sulfination reaction Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229940066767 systemic antihistamines phenothiazine derivative Drugs 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- PTVAFUMXLZLZEZ-UHFFFAOYSA-N tert-butyl 2-(3-ethenylphenoxy)acetate Chemical compound CC(C)(C)OC(=O)COC1=CC=CC(C=C)=C1 PTVAFUMXLZLZEZ-UHFFFAOYSA-N 0.000 description 1
- AIBKTSSWLZGMLQ-UHFFFAOYSA-N tert-butyl 2-(4-ethenylphenoxy)acetate Chemical compound CC(C)(C)OC(=O)COC1=CC=C(C=C)C=C1 AIBKTSSWLZGMLQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- XYWJAMWDOXEIIP-UHFFFAOYSA-N tert-butyl 3-ethenylbenzoate Chemical compound CC(C)(C)OC(=O)C1=CC=CC(C=C)=C1 XYWJAMWDOXEIIP-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
- IBOKZQNMFSHYNQ-UHFFFAOYSA-N tribromosilane Chemical compound Br[SiH](Br)Br IBOKZQNMFSHYNQ-UHFFFAOYSA-N 0.000 description 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 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
- DNAPJAGHXMPFLD-UHFFFAOYSA-N triiodosilane Chemical compound I[SiH](I)I DNAPJAGHXMPFLD-UHFFFAOYSA-N 0.000 description 1
- LGMUVWLDYISOQX-UHFFFAOYSA-N trimethyl(2-phenylethenoxy)silane Chemical compound C[Si](C)(C)OC=CC1=CC=CC=C1 LGMUVWLDYISOQX-UHFFFAOYSA-N 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
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 125000005289 uranyl group Chemical group 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 238000001771 vacuum deposition Methods 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
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 210000004127 vitreous body Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent 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
- 238000004383 yellowing Methods 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
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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06112602.5 | 2006-04-13 | ||
| EP06112602 | 2006-04-13 | ||
| PCT/EP2007/053280 WO2007118794A1 (en) | 2006-04-13 | 2007-04-04 | Sulphonium salt initiators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20080112377A KR20080112377A (ko) | 2008-12-24 |
| KR101389057B1 true KR101389057B1 (ko) | 2014-05-13 |
Family
ID=36703163
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020087027838A Active KR101389057B1 (ko) | 2006-04-13 | 2007-04-04 | 설포늄 염 개시제 |
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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20190059327A (ko) * | 2016-10-17 | 2019-05-30 | 도요 고세이 고교 가부시키가이샤 | 조성물 및 이를 이용한 디바이스의 제조 방법 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20190059327A (ko) * | 2016-10-17 | 2019-05-30 | 도요 고세이 고교 가부시키가이샤 | 조성물 및 이를 이용한 디바이스의 제조 방법 |
| KR102278416B1 (ko) * | 2016-10-17 | 2021-07-15 | 도요 고세이 고교 가부시키가이샤 | 조성물 및 이를 이용한 디바이스의 제조 방법 |
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 |
| TWI404699B (zh) | 2013-08-11 |
| WO2007118794A1 (en) | 2007-10-25 |
| TW200804260A (en) | 2008-01-16 |
| WO2007118794B1 (en) | 2008-01-03 |
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