CA2452566C - Sulfonium salts, methods for their preparation and use thereof as photoinitiators for radiation curable systems - Google Patents
Sulfonium salts, methods for their preparation and use thereof as photoinitiators for radiation curable systems Download PDFInfo
- Publication number
- CA2452566C CA2452566C CA2452566A CA2452566A CA2452566C CA 2452566 C CA2452566 C CA 2452566C CA 2452566 A CA2452566 A CA 2452566A CA 2452566 A CA2452566 A CA 2452566A CA 2452566 C CA2452566 C CA 2452566C
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- Prior art keywords
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- compound
- radiation curable
- curable composition
- linear
- Prior art date
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- 230000005855 radiation Effects 0.000 title claims abstract description 34
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims abstract description 13
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 239000000203 mixture Substances 0.000 claims abstract description 88
- 150000001875 compounds Chemical class 0.000 claims description 65
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 35
- -1 O-alkyl Chemical group 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 14
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical group CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 239000011707 mineral Substances 0.000 claims description 7
- 229960000834 vinyl ether Drugs 0.000 claims description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- 239000002841 Lewis acid Substances 0.000 claims description 6
- 150000007517 lewis acids Chemical class 0.000 claims description 6
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 5
- 150000001768 cations Chemical class 0.000 claims description 5
- 239000012669 liquid formulation Substances 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 5
- 150000001451 organic peroxides Chemical class 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- CYIGRWUIQAVBFG-UHFFFAOYSA-N 1,2-bis(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOCCOC=C CYIGRWUIQAVBFG-UHFFFAOYSA-N 0.000 claims description 4
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 4
- HMBNQNDUEFFFNZ-UHFFFAOYSA-N 4-ethenoxybutan-1-ol Chemical compound OCCCCOC=C HMBNQNDUEFFFNZ-UHFFFAOYSA-N 0.000 claims description 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 229910052787 antimony Inorganic materials 0.000 claims description 4
- 229910052785 arsenic Inorganic materials 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 125000005062 perfluorophenyl group Chemical group FC1=C(C(=C(C(=C1F)F)F)F)* 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- ZKJNETINGMOHJG-GGWOSOGESA-N (e)-1-[(e)-prop-1-enoxy]prop-1-ene Chemical compound C\C=C\O\C=C\C ZKJNETINGMOHJG-GGWOSOGESA-N 0.000 claims description 2
- DQNSRQYYCSXZDF-UHFFFAOYSA-N 1,4-bis(ethenoxymethyl)cyclohexane Chemical compound C=COCC1CCC(COC=C)CC1 DQNSRQYYCSXZDF-UHFFFAOYSA-N 0.000 claims description 2
- WVXLLHWEQSZBLW-UHFFFAOYSA-N 2-(4-acetyl-2-methoxyphenoxy)acetic acid Chemical compound COC1=CC(C(C)=O)=CC=C1OCC(O)=O WVXLLHWEQSZBLW-UHFFFAOYSA-N 0.000 claims description 2
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 150000004292 cyclic ethers Chemical class 0.000 claims description 2
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 2
- 150000002118 epoxides Chemical class 0.000 claims description 2
- 150000002596 lactones Chemical class 0.000 claims description 2
- 229920001296 polysiloxane Polymers 0.000 claims description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims 4
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 239000000243 solution Substances 0.000 description 31
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 239000007787 solid Substances 0.000 description 22
- 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
- 238000010992 reflux Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 229950011008 tetrachloroethylene Drugs 0.000 description 9
- 125000002723 alicyclic group Chemical group 0.000 description 8
- 125000004103 aminoalkyl group Chemical group 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000009472 formulation Methods 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 239000007832 Na2SO4 Substances 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 125000002091 cationic group Chemical group 0.000 description 5
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 238000000967 suction filtration Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 125000005358 mercaptoalkyl group Chemical group 0.000 description 4
- 238000011417 postcuring Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 2
- 150000001450 anions Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000012952 cationic photoinitiator Substances 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000007336 electrophilic substitution reaction Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 125000005409 triarylsulfonium group Chemical group 0.000 description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- XEAFUAINQLFYSI-UHFFFAOYSA-N 1,7-dimethylthianthrene Chemical compound C1=CC=C2SC3=CC(C)=CC=C3SC2=C1C XEAFUAINQLFYSI-UHFFFAOYSA-N 0.000 description 1
- SXTMNGDJQBHXPU-UHFFFAOYSA-N 10-oxo-1-propan-2-ylthioxanthen-9-one Chemical compound O=C1C2=CC=CC=C2S(=O)C2=C1C(C(C)C)=CC=C2 SXTMNGDJQBHXPU-UHFFFAOYSA-N 0.000 description 1
- YEZOVIIHKKPUOS-UHFFFAOYSA-N 10-oxothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3S(=O)C2=C1 YEZOVIIHKKPUOS-UHFFFAOYSA-N 0.000 description 1
- QSBOBPNCSTVAQE-UHFFFAOYSA-N 2-ethenoxy-3-ethyloxirane Chemical compound C(=C)OC1C(CC)O1 QSBOBPNCSTVAQE-UHFFFAOYSA-N 0.000 description 1
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
- 229910017048 AsF6 Inorganic materials 0.000 description 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- PFHLXMMCWCWAMA-UHFFFAOYSA-N [4-(4-diphenylsulfoniophenyl)sulfanylphenyl]-diphenylsulfanium Chemical compound C=1C=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1SC(C=C1)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 PFHLXMMCWCWAMA-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- ILFFFKFZHRGICY-UHFFFAOYSA-N anthracene-1-sulfonic acid Chemical compound C1=CC=C2C=C3C(S(=O)(=O)O)=CC=CC3=CC2=C1 ILFFFKFZHRGICY-UHFFFAOYSA-N 0.000 description 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000003988 headspace gas chromatography Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 150000002921 oxetanes Chemical class 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 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
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/08—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
- C07D335/14—Thioxanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
- C07D335/16—Oxygen atoms, e.g. thioxanthones
-
- 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
-
- 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)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerization Catalysts (AREA)
- Polymerisation Methods In General (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Epoxy Resins (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2001MI001543A ITMI20011543A1 (it) | 2001-07-19 | 2001-07-19 | Sali di solfonio processo di preparazione e loro impiego come fotoiniziatori di composizioni polimerizzabili mediante radizioni elettromagne |
| ITMI01A001543 | 2001-07-19 | ||
| IT2001MI001544A ITMI20011544A1 (it) | 2001-07-19 | 2001-07-19 | Sali di solfonio processo di preparazione e loro impiego come fotoinziatori di composizioni polimerizzabili meidante radiazioni elettromagne |
| ITMI01A001544 | 2001-07-19 | ||
| PCT/EP2002/007415 WO2003008404A2 (en) | 2001-07-19 | 2002-07-04 | Sulfonium salts as phtoinitiators for radiation curable systems |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2452566A1 CA2452566A1 (en) | 2003-01-30 |
| CA2452566C true CA2452566C (en) | 2011-08-23 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2452566A Expired - Fee Related CA2452566C (en) | 2001-07-19 | 2002-07-04 | Sulfonium salts, methods for their preparation and use thereof as photoinitiators for radiation curable systems |
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| EP (1) | EP1417198B1 (enExample) |
| JP (1) | JP4480393B2 (enExample) |
| KR (1) | KR100918556B1 (enExample) |
| CN (1) | CN1269812C (enExample) |
| AT (1) | ATE438638T1 (enExample) |
| AU (1) | AU2002331332A1 (enExample) |
| BR (1) | BR0205767B1 (enExample) |
| CA (1) | CA2452566C (enExample) |
| DE (1) | DE60233234D1 (enExample) |
| ES (1) | ES2329345T3 (enExample) |
| WO (1) | WO2003008404A2 (enExample) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4701231B2 (ja) * | 2002-02-13 | 2011-06-15 | 富士フイルム株式会社 | 電子線、ｅｕｖ又はｘ線用ネガ型レジスト組成物及びそれを用いたパターン形成方法 |
| GB0204468D0 (en) * | 2002-02-26 | 2002-04-10 | Coates Brothers Plc | Novel thioxanthone derivatives, and their use as cationic photoinitiators |
| GB0204467D0 (en) * | 2002-02-26 | 2002-04-10 | Coates Brothers Plc | Novel fused ring compounds, and their use as cationic photoinitiators |
| EP1504306A1 (en) * | 2002-05-16 | 2005-02-09 | Rensselaer Polytechnic Institute | Photopolymerizable compositions comprising thianthrenium salts as cationic photoinitiators |
| KR101197539B1 (ko) * | 2003-11-04 | 2012-11-12 | 헨켈 아게 운트 코. 카게아아 | 술포늄염 광개시제 및 그의 용도 |
| US7230122B2 (en) | 2003-11-04 | 2007-06-12 | National Starch And Chemical Investment Holding Corporation | Sulfonium salt photinitiators and use thereof |
| JP2005263897A (ja) * | 2004-03-17 | 2005-09-29 | Konica Minolta Medical & Graphic Inc | インクジェット用インク組成物及び画像形成方法 |
| JP2008506826A (ja) * | 2004-07-21 | 2008-03-06 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | 光活性化方法及び逆転した２段階工程による触媒の使用 |
| JP4439409B2 (ja) * | 2005-02-02 | 2010-03-24 | 富士フイルム株式会社 | レジスト組成物及びそれを用いたパターン形成方法 |
| JP4677353B2 (ja) * | 2005-02-18 | 2011-04-27 | 富士フイルム株式会社 | レジスト組成物、該レジスト組成物に用いる化合物及び該レジスト組成物を用いたパターン形成方法 |
| US7541131B2 (en) * | 2005-02-18 | 2009-06-02 | Fujifilm Corporation | Resist composition, compound for use in the resist composition and pattern forming method using the resist composition |
| JP4505357B2 (ja) * | 2005-03-16 | 2010-07-21 | 富士フイルム株式会社 | 感光性組成物、該感光性組成物に用いる化合物及び該感光性組成物を用いたパターン形成方法 |
| DE602006015319D1 (de) * | 2005-07-01 | 2010-08-19 | Basf Se | Sulfoniumsalzinitiatoren |
| JP4792299B2 (ja) * | 2006-02-07 | 2011-10-12 | 富士フイルム株式会社 | 新規なスルホニウム化合物、該化合物を含有する感光性組成物及び該感光性組成物を用いたパターン形成方法 |
| JP2007254454A (ja) * | 2006-02-23 | 2007-10-04 | Fujifilm Corp | スルホニウム塩、硬化性組成物、インク組成物、インクジェット記録方法、印刷物、平版印刷版の製造方法、及び、平版印刷版 |
| JP5313873B2 (ja) | 2006-04-13 | 2013-10-09 | チバ ホールディング インコーポレーテッド | スルホニウム塩開始剤 |
| EP2125713B1 (en) | 2006-10-04 | 2012-04-18 | Basf Se | Sulphonium salt photoinitiators |
| JP4936848B2 (ja) * | 2006-10-16 | 2012-05-23 | 旭化成イーマテリアルズ株式会社 | 感光性樹脂組成物およびその積層体 |
| CN101558110B (zh) * | 2006-10-24 | 2012-06-13 | 西巴控股有限公司 | 热稳定的可阳离子光固化组合物 |
| RU2330033C1 (ru) * | 2007-01-09 | 2008-07-27 | Новосибирский институт органической химии им. Н.Н. Ворожцова СО РАН (НИОХ СО РАН) | Гексафторфосфат 2-(2-тозил-2-метилпропионил)-9-оксо-10-(4-гептилоксифенил)-9н-тиоксантения как инициатор фотополимеризации непредельных соединений |
| US7488568B2 (en) * | 2007-04-09 | 2009-02-10 | Tokyo Ohka Kogyo Co., Ltd. | Resist composition, method of forming resist pattern, compound and acid generator |
| JP4866790B2 (ja) * | 2007-05-23 | 2012-02-01 | 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 |
| JP5066405B2 (ja) * | 2007-08-02 | 2012-11-07 | 富士フイルム株式会社 | 電子線、ｘ線又はｅｕｖ用レジスト組成物及び該組成物を用いたパターン形成方法 |
| EP2197839B1 (en) | 2007-10-10 | 2013-01-02 | Basf Se | Sulphonium salt initiators |
| JP5473921B2 (ja) | 2007-10-10 | 2014-04-16 | 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 |
| JP5570424B2 (ja) | 2007-10-10 | 2014-08-13 | 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 |
| US9005871B2 (en) | 2008-10-20 | 2015-04-14 | Basf Se | Sulfonium derivatives and the use therof as latent acids |
| JP2010235911A (ja) | 2009-03-11 | 2010-10-21 | Konica Minolta Ij Technologies Inc | 活性エネルギー線硬化型インクジェットインク、インクジェット記録方法及び印刷物 |
| JP5964007B2 (ja) | 2009-04-02 | 2016-08-03 | コニカミノルタ株式会社 | 活性エネルギー線硬化型インクジェットインク、インクジェット記録方法及び印刷物 |
| DE102016111590A1 (de) | 2016-06-24 | 2017-12-28 | Delo Industrie Klebstoffe Gmbh & Co. Kgaa | Einkomponentenmasse auf Basis von Alkoxysilanen und Verfahren zum Fügen oder Vergießen von Bauteilen unter Verwendung der Masse |
| DE102017126215A1 (de) | 2017-11-09 | 2019-05-09 | Delo Industrie Klebstoffe Gmbh & Co. Kgaa | Verfahren zur Erzeugung opaker Beschichtungen, Verklebungen und Vergüsse sowie härtbare Masse zur Verwendung in dem Verfahren |
| DE102018127854A1 (de) | 2018-11-08 | 2020-05-14 | Delo Industrie Klebstoffe Gmbh & Co. Kgaa | Feuchtigkeitshärtbare Einkomponentenmasse und Verfahren zum Fügen, Vergießen und Beschichten unter Verwendung der Masse |
| DE102018131513A1 (de) | 2018-12-10 | 2020-06-10 | Delo Industrie Klebstoffe Gmbh & Co. Kgaa | Kationisch härtbare Masse und Verfahren zum Fügen, Vergießen und Beschichten von Substraten unter Verwendung der Masse |
| CN118271281A (zh) * | 2022-12-30 | 2024-07-02 | 常州强力电子新材料股份有限公司 | 一种噻吨硫鎓盐光引发剂及其制备方法和应用 |
| GB2640960A (en) | 2024-05-10 | 2025-11-12 | Henkel Ag & Co Kgaa | Debonding of a cured composition |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4161478A (en) * | 1974-05-02 | 1979-07-17 | General Electric Company | Photoinitiators |
| JPS61190524A (ja) * | 1985-01-25 | 1986-08-25 | Asahi Denka Kogyo Kk | エネルギ−線硬化性組成物 |
| JPH04161478A (ja) * | 1990-10-26 | 1992-06-04 | Matsushita Electric Works Ltd | 蓄熱体 |
| TW237466B (enExample) | 1992-07-21 | 1995-01-01 | Giba Gerigy Ag | |
| US5731364A (en) * | 1996-01-24 | 1998-03-24 | Shipley Company, L.L.C. | Photoimageable compositions comprising multiple arylsulfonium photoactive compounds |
| DE69800164T2 (de) | 1997-03-31 | 2000-10-05 | Fuji Photo Film Co., Ltd. | Positiv-arbeitende photoempfindliche Zusammensetzung |
| GB0204467D0 (en) * | 2002-02-26 | 2002-04-10 | Coates Brothers Plc | Novel fused ring compounds, and their use as cationic photoinitiators |
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2002
- 2002-07-04 BR BRPI0205767-0B1A patent/BR0205767B1/pt not_active IP Right Cessation
- 2002-07-04 KR KR1020037003928A patent/KR100918556B1/ko not_active Expired - Fee Related
- 2002-07-04 US US10/484,358 patent/US7230121B2/en not_active Expired - Lifetime
- 2002-07-04 EP EP02767172A patent/EP1417198B1/en not_active Expired - Lifetime
- 2002-07-04 DE DE60233234T patent/DE60233234D1/de not_active Expired - Lifetime
- 2002-07-04 CA CA2452566A patent/CA2452566C/en not_active Expired - Fee Related
- 2002-07-04 AU AU2002331332A patent/AU2002331332A1/en not_active Abandoned
- 2002-07-04 CN CNB028145038A patent/CN1269812C/zh not_active Expired - Fee Related
- 2002-07-04 WO PCT/EP2002/007415 patent/WO2003008404A2/en not_active Ceased
- 2002-07-04 AT AT02767172T patent/ATE438638T1/de not_active IP Right Cessation
- 2002-07-04 JP JP2003513963A patent/JP4480393B2/ja not_active Expired - Lifetime
- 2002-07-04 ES ES02767172T patent/ES2329345T3/es not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AU2002331332A1 (en) | 2003-03-03 |
| US7230121B2 (en) | 2007-06-12 |
| ES2329345T3 (es) | 2009-11-25 |
| WO2003008404A2 (en) | 2003-01-30 |
| KR100918556B1 (ko) | 2009-09-21 |
| BR0205767A (pt) | 2003-08-12 |
| CA2452566A1 (en) | 2003-01-30 |
| EP1417198A2 (en) | 2004-05-12 |
| JP2005501040A (ja) | 2005-01-13 |
| KR20040015008A (ko) | 2004-02-18 |
| CN1533386A (zh) | 2004-09-29 |
| ATE438638T1 (de) | 2009-08-15 |
| BR0205767B1 (pt) | 2013-10-15 |
| DE60233234D1 (en) | 2009-09-17 |
| CN1269812C (zh) | 2006-08-16 |
| US20040242901A1 (en) | 2004-12-02 |
| JP4480393B2 (ja) | 2010-06-16 |
| EP1417198B1 (en) | 2009-08-05 |
| WO2003008404A3 (en) | 2003-08-28 |
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