TWI435864B - 鹽起始劑 - Google Patents
鹽起始劑 Download PDFInfo
- Publication number
- TWI435864B TWI435864B TW096137050A TW96137050A TWI435864B TW I435864 B TWI435864 B TW I435864B TW 096137050 A TW096137050 A TW 096137050A TW 96137050 A TW96137050 A TW 96137050A TW I435864 B TWI435864 B TW I435864B
- Authority
- TW
- Taiwan
- Prior art keywords
- group
- compound
- acid
- alkyl
- substituted
- Prior art date
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- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 title description 2
- 239000003999 initiator Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 177
- 239000002253 acid Substances 0.000 claims abstract description 75
- 239000001257 hydrogen Substances 0.000 claims abstract description 66
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 66
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 25
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 24
- 125000001424 substituent group Chemical group 0.000 claims abstract description 20
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims abstract description 11
- 150000001449 anionic compounds Chemical class 0.000 claims abstract description 9
- 150000002891 organic anions Chemical class 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims description 118
- 238000000576 coating method Methods 0.000 claims description 71
- 125000000217 alkyl group Chemical group 0.000 claims description 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 239000011248 coating agent Substances 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 39
- 229920005989 resin Polymers 0.000 claims description 39
- 239000011347 resin Substances 0.000 claims description 39
- 150000002431 hydrogen Chemical class 0.000 claims description 33
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 238000004519 manufacturing process Methods 0.000 claims description 28
- 150000002367 halogens Chemical class 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 26
- 229920002554 vinyl polymer Polymers 0.000 claims description 25
- 150000001450 anions Chemical class 0.000 claims description 24
- 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 24
- 229920002120 photoresistant polymer Polymers 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 23
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 21
- 238000007639 printing Methods 0.000 claims description 21
- 230000005855 radiation Effects 0.000 claims description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 19
- 239000000463 material Substances 0.000 claims description 19
- 239000000976 ink Substances 0.000 claims description 18
- 239000000843 powder Substances 0.000 claims description 16
- 239000000758 substrate Substances 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000006755 (C2-C20) alkyl group Chemical group 0.000 claims description 14
- 125000002091 cationic group Chemical group 0.000 claims description 14
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 14
- 239000000654 additive Substances 0.000 claims description 13
- 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 13
- 239000008199 coating composition Substances 0.000 claims description 12
- 238000004132 cross linking Methods 0.000 claims description 11
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 239000000853 adhesive Substances 0.000 claims description 9
- 230000001070 adhesive effect Effects 0.000 claims description 9
- 239000002131 composite material Substances 0.000 claims description 8
- 229910001412 inorganic anion Inorganic materials 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 230000000181 anti-adherent effect Effects 0.000 claims description 6
- 239000000835 fiber Substances 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 5
- 238000010894 electron beam technology Methods 0.000 claims description 5
- 239000005977 Ethylene Substances 0.000 claims description 4
- 230000009471 action Effects 0.000 claims description 4
- 150000001767 cationic compounds Chemical class 0.000 claims description 4
- 229910001411 inorganic cation Inorganic materials 0.000 claims description 4
- 150000002892 organic cations Chemical class 0.000 claims description 4
- 239000006120 scratch resistant coating Substances 0.000 claims description 4
- 239000007921 spray Substances 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 239000011350 dental composite resin Substances 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 2
- 238000005260 corrosion Methods 0.000 claims description 2
- 230000005670 electromagnetic radiation Effects 0.000 claims description 2
- 238000010186 staining Methods 0.000 claims 1
- -1 bis(4-phenoxyphenyl)phosphonium hexafluorophosphate Chemical compound 0.000 description 206
- 229920000180 alkyd Polymers 0.000 description 62
- 238000006243 chemical reaction Methods 0.000 description 43
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 37
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 229920000642 polymer Polymers 0.000 description 29
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 28
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 229920005862 polyol Polymers 0.000 description 25
- 238000009472 formulation Methods 0.000 description 24
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 23
- 229920001577 copolymer Polymers 0.000 description 22
- 239000000178 monomer Substances 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- 239000002904 solvent Substances 0.000 description 22
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 21
- 229960000834 vinyl ether Drugs 0.000 description 21
- 239000000049 pigment Substances 0.000 description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 125000003277 amino group Chemical group 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
- 229920000877 Melamine resin Polymers 0.000 description 17
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 17
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 17
- 150000002148 esters Chemical class 0.000 description 17
- 125000000524 functional group Chemical group 0.000 description 17
- 150000003077 polyols Chemical class 0.000 description 17
- 239000000126 substance Substances 0.000 description 17
- 238000005160 1H NMR spectroscopy Methods 0.000 description 16
- 239000004925 Acrylic resin Substances 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 16
- 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000004593 Epoxy Substances 0.000 description 15
- 229920000647 polyepoxide Polymers 0.000 description 15
- 229920000728 polyester Polymers 0.000 description 15
- 239000000600 sorbitol Substances 0.000 description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 14
- 239000011230 binding agent Substances 0.000 description 14
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 13
- 150000001412 amines Chemical class 0.000 description 13
- 239000010410 layer Substances 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- 229920000058 polyacrylate Polymers 0.000 description 13
- 150000003254 radicals Chemical class 0.000 description 13
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 12
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 12
- 150000001241 acetals Chemical class 0.000 description 12
- 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 12
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- 150000007513 acids Chemical class 0.000 description 11
- 125000001931 aliphatic group Chemical group 0.000 description 11
- 125000003700 epoxy group Chemical group 0.000 description 11
- 229920001228 polyisocyanate Polymers 0.000 description 11
- 239000005056 polyisocyanate Substances 0.000 description 11
- 239000004814 polyurethane Substances 0.000 description 11
- 229920002635 polyurethane Polymers 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 239000002585 base Substances 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 10
- 239000002655 kraft paper Substances 0.000 description 10
- 229920001225 polyester resin Polymers 0.000 description 10
- 239000004645 polyester resin Substances 0.000 description 10
- 229920000570 polyether Polymers 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000003822 epoxy resin Substances 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 239000012948 isocyanate Substances 0.000 description 9
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 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 8
- 229920000178 Acrylic resin Polymers 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- 238000007259 addition reaction Methods 0.000 description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 239000000975 dye Substances 0.000 description 8
- 238000005516 engineering process Methods 0.000 description 8
- 230000032050 esterification Effects 0.000 description 8
- 238000005886 esterification reaction Methods 0.000 description 8
- 229940052303 ethers for general anesthesia Drugs 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 8
- 229920000768 polyamine Polymers 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 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
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 7
- 239000004640 Melamine resin Substances 0.000 description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- 239000002274 desiccant Substances 0.000 description 7
- 125000004185 ester group Chemical group 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 235000011187 glycerol Nutrition 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
- 150000002576 ketones Chemical class 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
- 239000012074 organic phase Substances 0.000 description 7
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 7
- 239000003381 stabilizer Substances 0.000 description 7
- 238000012546 transfer Methods 0.000 description 7
- 239000004721 Polyphenylene oxide Substances 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
- 229910052797 bismuth Inorganic materials 0.000 description 6
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 239000012952 cationic photoinitiator Substances 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 150000002118 epoxides Chemical class 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- WSFJFIDCQBAQQZ-UHFFFAOYSA-N hydroxy(sulfido)phosphanium Chemical class S[PH2]=O WSFJFIDCQBAQQZ-UHFFFAOYSA-N 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
- 239000003607 modifier Substances 0.000 description 6
- 229920003986 novolac Polymers 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
- 239000011541 reaction mixture Substances 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 5
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-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
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 150000008064 anhydrides Chemical group 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
- 239000012965 benzophenone Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 description 5
- 229940116229 borneol Drugs 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 238000006555 catalytic reaction Methods 0.000 description 5
- RRGUKTPIGVIEKM-UHFFFAOYSA-N cilostazol Chemical compound C=1C=C2NC(=O)CCC2=CC=1OCCCCC1=NN=NN1C1CCCCC1 RRGUKTPIGVIEKM-UHFFFAOYSA-N 0.000 description 5
- 229960004588 cilostazol Drugs 0.000 description 5
- 238000006482 condensation reaction Methods 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 150000005690 diesters Chemical class 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 230000000269 nucleophilic effect Effects 0.000 description 5
- 150000004714 phosphonium salts Chemical class 0.000 description 5
- 239000003504 photosensitizing agent Substances 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
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- CLZWAWBPWVRRGI-UHFFFAOYSA-N tert-butyl 2-[2-[2-[2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]-5-bromophenoxy]ethoxy]-4-methyl-n-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]anilino]acetate Chemical compound CC1=CC=C(N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)C(OCCOC=2C(=CC=C(Br)C=2)N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)=C1 CLZWAWBPWVRRGI-UHFFFAOYSA-N 0.000 description 1
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- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
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- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B33—ADDITIVE MANUFACTURING TECHNOLOGY
- B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
- B33Y70/00—Materials specially adapted for additive manufacturing
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B33—ADDITIVE MANUFACTURING TECHNOLOGY
- B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
- B33Y80/00—Products made by additive manufacturing
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/375—Thiols containing six-membered aromatic rings
-
- 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paints Or Removers (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (1)
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| EP06121699 | 2006-10-04 |
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| AT (1) | ATE554065T1 (enExample) |
| TW (1) | TWI435864B (enExample) |
| WO (1) | WO2008040648A1 (enExample) |
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| 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 |
| 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 |
| KR20110025211A (ko) * | 2008-06-12 | 2011-03-09 | 바스프 에스이 | 술포늄 유도체 및 잠재성 산으로서의 그의 용도 |
| CN102077381B (zh) | 2008-06-27 | 2014-10-22 | 通用显示公司 | 可交联的离子掺杂剂 |
| JP5398246B2 (ja) * | 2008-12-10 | 2014-01-29 | 東京応化工業株式会社 | レジスト組成物およびレジストパターン形成方法 |
| EP2199856B1 (en) * | 2008-12-18 | 2013-08-07 | Agfa Graphics N.V. | Cationic radiation curable compositions |
| 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 |
| CN102781911B (zh) | 2010-02-24 | 2015-07-22 | 巴斯夫欧洲公司 | 潜酸及其用途 |
| CN102566277B (zh) * | 2010-12-21 | 2013-11-06 | 北京师范大学 | 一种用于高感度光聚合版材的阳离子聚合成像组合物 |
| US8816211B2 (en) * | 2011-02-14 | 2014-08-26 | Eastman Kodak Company | Articles with photocurable and photocured compositions |
| JP5993626B2 (ja) * | 2011-06-24 | 2016-09-14 | 住友化学株式会社 | 塩及び着色硬化性組成物 |
| KR101263673B1 (ko) * | 2011-08-03 | 2013-05-22 | 금호석유화학 주식회사 | 술포늄 화합물, 광산발생제 및 레지스트 조성물 |
| TW201335295A (zh) | 2011-11-30 | 2013-09-01 | 西克帕控股公司 | 經標記之塗層組成物及其認證之方法 |
| JP6120574B2 (ja) * | 2012-01-31 | 2017-04-26 | キヤノン株式会社 | 感光性ネガ型樹脂組成物、微細構造体、微細構造体の製造方法及び液体吐出ヘッド |
| EP2882597B1 (en) | 2012-08-01 | 2017-02-01 | Sicpa Holding SA | Optically variable security threads and stripes |
| EA028728B1 (ru) | 2012-10-29 | 2017-12-29 | Сикпа Холдинг Са | Защитные покрытия для защищенных документов |
| JP5638106B2 (ja) * | 2013-05-08 | 2014-12-10 | 東京応化工業株式会社 | 新規な化合物および酸発生剤 |
| JP6621271B2 (ja) * | 2014-09-26 | 2019-12-18 | 東京応化工業株式会社 | ビニル基含有化合物を含有する硬化性組成物 |
| TW201703879A (zh) | 2015-06-02 | 2017-02-01 | 西克帕控股有限公司 | 用於生產光學效應層之製程 |
| WO2017014284A1 (ja) * | 2015-07-23 | 2017-01-26 | 三菱瓦斯化学株式会社 | 新規化合物及びその製造方法 |
| EP3185655B8 (de) * | 2015-12-22 | 2024-01-03 | Heraeus Electronics GmbH & Co. KG | Verfahren zur individuellen codierung von metall-keramik-substraten |
| CN105712917B (zh) * | 2016-03-29 | 2017-12-26 | 同济大学 | 具有光引发剂与光敏化剂双重功能的共轭型硫鎓盐光引发剂、制备方法及其应用 |
| 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 |
| 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 |
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| US8067643B2 (en) | 2006-04-13 | 2011-11-29 | Basf Se | Sulphonium salt initiators |
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2007
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- 2007-09-24 AT AT07820481T patent/ATE554065T1/de active
- 2007-09-24 WO PCT/EP2007/060074 patent/WO2008040648A1/en not_active Ceased
- 2007-09-24 CN CN2007800372746A patent/CN101522613B/zh not_active Expired - Fee Related
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| CN101522613A (zh) | 2009-09-02 |
| CN101522613B (zh) | 2013-03-06 |
| EP2125713A1 (en) | 2009-12-02 |
| JP2010505787A (ja) | 2010-02-25 |
| JP5290183B2 (ja) | 2013-09-18 |
| EP2125713B1 (en) | 2012-04-18 |
| TW200831452A (en) | 2008-08-01 |
| US20100087563A1 (en) | 2010-04-08 |
| ATE554065T1 (de) | 2012-05-15 |
| WO2008040648A1 (en) | 2008-04-10 |
| US8012672B2 (en) | 2011-09-06 |
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