JP2001513765A - α−アンモニウムケトン、イミニウムケトンまたはアミジニウムケトンおよびアリールボラートに基づく、光による活性化が可能な窒素含有塩基 - Google Patents
α−アンモニウムケトン、イミニウムケトンまたはアミジニウムケトンおよびアリールボラートに基づく、光による活性化が可能な窒素含有塩基Info
- Publication number
- JP2001513765A JP2001513765A JP53724898A JP53724898A JP2001513765A JP 2001513765 A JP2001513765 A JP 2001513765A JP 53724898 A JP53724898 A JP 53724898A JP 53724898 A JP53724898 A JP 53724898A JP 2001513765 A JP2001513765 A JP 2001513765A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- group
- poly
- formula
- alkyl
- 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.)
- Granted
Links
- -1 amidinium ketones Chemical class 0.000 title claims abstract description 266
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 239000000203 mixture Substances 0.000 claims abstract description 65
- 238000000034 method Methods 0.000 claims abstract description 19
- 238000004519 manufacturing process Methods 0.000 claims abstract description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
- 229920000058 polyacrylate Polymers 0.000 claims description 32
- 238000000576 coating method Methods 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 229920000647 polyepoxide Polymers 0.000 claims description 21
- 229920000642 polymer Polymers 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 229920000728 polyester Polymers 0.000 claims description 18
- 125000001544 thienyl group Chemical group 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 229920001228 polyisocyanate Polymers 0.000 claims description 15
- 239000005056 polyisocyanate Substances 0.000 claims description 15
- 239000000758 substrate Substances 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 239000003822 epoxy resin Substances 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000001931 aliphatic group Chemical group 0.000 claims description 13
- 229920001577 copolymer Polymers 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000004018 acid anhydride group Chemical group 0.000 claims description 9
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000005561 phenanthryl group Chemical group 0.000 claims description 9
- 239000004593 Epoxy Substances 0.000 claims description 8
- 238000007259 addition reaction Methods 0.000 claims description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 8
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 8
- 239000012948 isocyanate Substances 0.000 claims description 8
- 150000002513 isocyanates Chemical class 0.000 claims description 8
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 claims description 8
- 125000001725 pyrenyl group Chemical group 0.000 claims description 8
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 7
- 150000002894 organic compounds Chemical class 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 150000004658 ketimines Chemical class 0.000 claims description 6
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 6
- 125000005493 quinolyl group Chemical group 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 5
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 5
- 125000005605 benzo group Chemical group 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 5
- 125000002346 iodo group Chemical group I* 0.000 claims description 5
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 5
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 5
- 125000005327 perimidinyl group Chemical group N1C(=NC2=CC=CC3=CC=CC1=C23)* 0.000 claims description 5
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 5
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 5
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 5
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 4
- 239000004925 Acrylic resin Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 4
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical group C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 238000000465 moulding Methods 0.000 claims description 4
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 4
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 4
- 125000005954 phenoxathiinyl group Chemical group 0.000 claims description 4
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 claims description 3
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 claims description 3
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 3
- 238000006073 displacement reaction Methods 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 150000004893 oxazines Chemical class 0.000 claims description 3
- 150000002917 oxazolidines Chemical class 0.000 claims description 3
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 claims description 2
- 125000005466 alkylenyl group Chemical group 0.000 claims description 2
- 229940125773 compound 10 Drugs 0.000 claims description 2
- 230000014509 gene expression Effects 0.000 claims description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 abstract description 10
- 150000002576 ketones Chemical class 0.000 abstract description 10
- 150000001642 boronic acid derivatives Chemical class 0.000 abstract description 7
- 238000005815 base catalysis Methods 0.000 abstract description 6
- 150000002466 imines Chemical class 0.000 abstract description 3
- 150000001409 amidines Chemical class 0.000 abstract description 2
- 239000002585 base Substances 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 20
- 238000004458 analytical method Methods 0.000 description 18
- 239000000178 monomer Substances 0.000 description 18
- 239000011248 coating agent Substances 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000010410 layer Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 239000011230 binding agent Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 239000012964 benzotriazole Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 7
- 238000001723 curing Methods 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 150000002170 ethers Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000004814 polyurethane Substances 0.000 description 5
- 229920002635 polyurethane Polymers 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000002131 composite material Substances 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002023 wood Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical group OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 3
- 239000003365 glass fiber Substances 0.000 description 3
- 150000002334 glycols Chemical class 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 239000004611 light stabiliser Substances 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 239000000123 paper Substances 0.000 description 3
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical class OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 2
- KBQNNOCVJFDHSC-UHFFFAOYSA-N (3-methylphenoxy)boronic acid Chemical class CC1=CC=CC(OB(O)O)=C1 KBQNNOCVJFDHSC-UHFFFAOYSA-N 0.000 description 2
- PHBVXHIVWULVNF-UHFFFAOYSA-N (4-fluorophenoxy)boronic acid Chemical class OB(O)OC1=CC=C(F)C=C1 PHBVXHIVWULVNF-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
- VVHFXJOCUKBZFS-UHFFFAOYSA-N 2-(chloromethyl)-2-methyloxirane Chemical compound ClCC1(C)CO1 VVHFXJOCUKBZFS-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
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- 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 1
- 125000004035 thiopropyl group Chemical group [H]SC([H])([H])C([H])([H])C([H])([H])* 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
- 238000004448 titration Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- KKFOMYPMTJLQGA-UHFFFAOYSA-N tribenzyl phosphite Chemical compound C=1C=CC=CC=1COP(OCC=1C=CC=CC=1)OCC1=CC=CC=C1 KKFOMYPMTJLQGA-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- JODJRDDQVZMRIY-UHFFFAOYSA-N trityloxyboronic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OB(O)O)C1=CC=CC=C1 JODJRDDQVZMRIY-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/04—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyesters
- C08F299/0485—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyesters from polyesters with side or terminal unsaturations
- C08F299/0492—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyesters from polyesters with side or terminal unsaturations the unsaturation being in acrylic or methacrylic groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/52—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides selected from boron, aluminium, gallium, indium, thallium or rare earths
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
- Polymerisation Methods In General (AREA)
- Polymerization Catalysts (AREA)
- Luminescent Compositions (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.下記式(I): で示される化合物。 式中、 mは、1または2であって、カチオンの正電荷数に相当し; R1は、フェニル、ナフチル、フェナントリル、アントラシル、ピレニル、5 ,6,7,8−テトラヒドロ−2−ナフチル、5,6,7,8−テトラヒドロ− 1−ナフチル、チエニル、ベンゾ[b]チエニル、ナフト[2,3−b]チエニ ル、チアトレニル、ジベンゾフリル、クロメニル、キサンテニル、チオキサンチ ル、フェノキサチイニル、ピロリル、イミダゾリル、ピラゾリル、ピラジニル、 ピリミジニル、ピリダジニル、インドリジニル、イソインドリル、インドリル、 インダゾリル、プリニル、キノリジニル、イソキノリル、キノリル、フタラジニ ル、ナフチリジニル、キノキサリニル、キナゾリニル、シンノリニル、プテリジ ニル、カルバゾリル、β−カルボリニル、フェナントリジニル、アクリジニル、 ペリミジニル、フェナントロリニル、フェナジニル、イソチアゾリル、フェノチ アジニル、イソキサゾリル、フラザニル、テルフェニル、スチルベニル、フルオ レニルまたはフェノキサジニルであって、これらの基は、非置換であるか、また はC1〜C18アルキル、C3〜C18アルケニル、C3〜C18アルキニル、C1〜C18 ハロアルキル、NO2、NR6R7、N3、OH、CN、OR8、SR8、C(O)R9 、C(O)OR10もしくはハロゲンによりモノまたはポリ置換されているか、 あるいは、R1は、化学式(A)または(B):の基であり; 式中、 R2、R3およびR4は、それぞれ互いに独立に、水素、C1〜C18アルキル、C3 〜C18アルケニル、C3〜C18アルキニルもしくはフェニルであり;またはR2 とR3および/もしくはR4とR3が、互いに独立にC2〜C12アルキレン架橋を形 成しているか;あるいはR2、R3、R4が、結合している窒素原子とともに、P1 、P2、P<t/4>型のホスファゼン塩基を、または、構造式(a)、(b)、(c )、(d)、(e)、(f)もしくは(g): の基を形成しており; 式中、 kおよびlは、それぞれ互いに独立に、2〜12の数であり; R5、R6、R7、R8、R9およびR10は、水素またはC1〜C18アルキルであり ;あるいは R5およびR1は、結合している炭素原子とともに、ベンゾシクロペンタノン基 を形成しており; R11は、C1〜C18アルキル、C2〜C18アルケニル、C2〜C18アルキニル、 C1〜C18ハロアルキル、NO2、NR6R7、OH、CN、OR8、SR8、 C(O)R9、C(O)OR10またはハロゲンであり;そして nは、0または1、2または3であり; R12、R13およびR14は、フェニルまたは他の芳香族炭化水素であって、これ らの基は、非置換であるか、またはC1〜C18アルキル、C3〜C18アルケニル、 C3〜C18アルキニル、C1〜C18ハロアルキル、NO2、OH、CN、OR8、S R8、C(O)R9、C(O)OR10もしくはハロゲンによりモノまたはポリ置換 されており; R15は、C1〜C18アルキル、フェニルまたは他の芳香族炭化水素であって、 該フェニル基または芳香族炭化水素基は、非置換であるか、またはC1〜C18ア ルキル、C3〜C18アルケニル、C3〜C18アルキニル、C1〜C18ハロアルキル 、NO2、OH、CN、OR8、SR8、C(O)R9、C(O)OR10もしくはハ ロゲンによってモノまたはポリ置換されており、あるいは R15は、式: に示す基であり;そして 式中、 Xは、C1〜C20アルキレン、−O−、−S−もしくはNR8によって中断され ているC2〜C20アルキレンであるか、またはXは式: に示すものであって、 R12、R13、R14およびR15が同時にフェニルである場合には、 (a)R2、R3およびR4が同時にはメチルでないこと;および (b)R2、R3およびR4はともに式: に示す基でないこと; の条件に合致する化合物。 2.R1が、フェニル、ナフチル、ピレニル、チオキサンチルまたはフェノチア ジニルであって、これらの基が、非置換であるか、またはC1〜C18アルキル、 C1〜C18ハロアルキル、NR6R7、CN、NO2、SR8もしくはOR8によって モノまたはポリ置換されている、請求項1に記載の化合物。 3.R2、R3およびR4が、互いに独立に水素、C1〜C18アルキルであるか、あ るいはR2とR3および/またはR4とR3が、互いに独立にC2〜C12アルキレン 架橋を形成しており;あるいはR2、R3、R4が、結合している窒素原子ととも に、構造式(a)、(b)、(c)、(d)、(e)、(f)、(g)、(h)の基、またはP1 、P2もしくはP<t/4>型のホスファゼン塩基を形成している、請求項1に 記載の化合物。 4.R2、R3およびR4が、互いに独立にC1〜C18アルキルであるか、あるいは R2、R3、R4が、結合している窒素原子とともに、構造式(a)、(b)、(c)、 (d)または(e)の基を形成している、請求項1に記載の化合物。 5.R12、R13およびR14が、フェニル、ビフェニル、ナフチル、アントラシル またはフェナントリルであって、これらの基が非置換であるか、あるいはC1〜 C18アルキル、C1〜C18ハロアルキル、NO2、OH、CN、OR8もしくはハ ロゲンによりモノまたはポリ置換されており、そして R15が、C1〜C18アルキルまたはフェニルであって、非置換であるか、ある いはC1〜C18アルキル、C1〜C18ハロアルキル、NO2、OH、CN、OR8も しくはハロゲンによりモノまたはポリ置換されている、請求項1に記載の化合物 。 6.化学式Iの化合物を製造する方法であって、第1段階として、式(II): NR2R3R4 (II) の窒素性塩基を、式(III): のα−ハロゲンケトンと反応させて、式(IV): の化合物とし、そして、第2段階で、式(IV)の化合物を、式(V): の化合物と反応させて、式(I)の化合物にすることを含み、 式中、 ハロゲンはブロモまたはヨードであり、MはNa、Kまたはアンモニウムであ り、そしてR1、R2、R3、R4、R5、R12、R13、R14およびR15は、請求項 1に記載の意味と好ましい意味とを有する方法。 7.組成物であって、 A)式(I)の化合物の少なくとも1種、および B)塩基触媒による付加反応または置換反応が可能な有機化合物の少なくとも1 種 を含む組成物。 8.成分B)が、アニオン重合可能または架橋可能である、請求項7に記載の組 成物。 9.成分B)が、下記の系のうちの1種である、請求項7に記載の組成物: a)アルコキシシランまたはアルコキシシロキサン側鎖基を有するアクリラート コポリマー、 b)水酸基を含有するポリアクリラートおよび/またはポリエステル、ならびに 脂肪族または芳香族ポリイソシアナートを含む2成分系、 c)官能性ポリアクリラートおよびポリエポキシドを含み、該ポリアクリラート がカルボキシルまたは酸無水物基を有する2成分系、 d)フッ素修飾もしくはシリコーン修飾されたヒドロキシル基を有するポリアク リラートまたはポリエステル、および脂肪族または芳香族ポリイソシアナートを 含む2成分系、 e)(ポリ)ケチミンおよび脂肪族または芳香族ポリイソシアナートを含む2成分 系、 f)(ポリ)ケチミン、および不飽和アクリラート樹脂またはアセトアセタート樹 脂もしくはメチルα−アクリルアミドメチルグリコラートを含む2成分系、 h)(ポリ)オキサゾリジン、および酸無水物基を有するポリアクリラート、また は不飽和アクリラート樹脂もしくはポリイソシアナートを含む2成分系、 i)エポキシ含有ポリアクリラートおよびカルボキシル基含有ポリアクラートを 含む2成分系、 l)アリルグリシジルエーテルに基づくポリマー、 m)(ポリ)アルコールおよび(ポリ)イソシアナートを含む2成分系、 n)α,β−エチレン性不飽和カルボニル化合物、および活性化CH2基を有す る化合物を含む2成分系。 10.成分B)が、下記の系のうちの1種である、請求項7に記載の組成物: b)水酸基を含有するポリアクリラート、および/またはポリエステル、ならび に脂肪族または芳香族ポリイソシアナートを含む2成分系、 c)官能性ポリアクリラートおよびポリエポキシドを含み、該ポリアクリラート がカルボキシルまたは酸無水物基を有する2成分系、 i)エポキシ含有ポリアクリラートおよびカルボキシル基含有ポリアクラートを 含む2成分系、 m)(ポリ)アルコールおよび(ポリ)イソシアナートを含む2成分系、 n)α,β−エチレン性不飽和カルボニル化合物、および活性化CH2基を有す る化合物を含む2成分系。 11.成分B)が、1種のエポキシ樹脂または異なるエポキシ樹脂の混合物であ る、請求項7に記載の組成物。 12.成分A)が、成分B)を基準にして、0.01〜10重量%の量で存在す る、請求項7に記載の組成物。 13.チオキサントン類、オキサジン類、アクリジン類、フェナジン類およびロ ーダミン類からなる群より選ばれた増感剤を追加的に含む、請求項7に記載の組 成物。 14.請求項7に記載の組成物を、波長200〜650nmの光に露光することを 含む、塩基触媒反応を実施する方法。 15.露光の前または後に組成物を加熱することを含む、請求項14に記載の方 法。 16.光化学的に誘起される塩基触媒付加反応または置換反応のための光開始剤 としての、請求項1に記載の有機化合物の使用。 17.コーティング材、成形用組成物または光形成層材料を製造するための、請 求項1に記載の有機化合物の使用。 18.請求項7に記載の組成物を用いて、少なくとも1個の表面を被覆された被 塗装基材。 19.請求項7に記載の、重合または架橋した組成物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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CH44497 | 1997-02-26 | ||
CH444/97 | 1997-02-26 | ||
PCT/EP1998/000846 WO1998038195A1 (en) | 1997-02-26 | 1998-02-14 | PHOTOACTIVATABLE NITROGEN-CONTAINING BASES BASED ON α-AMMONIUM KETONES, IMINIUM KETONES OR AMIDINIUM KETONES AND ARYL BORATES |
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JP2001513765A true JP2001513765A (ja) | 2001-09-04 |
JP2001513765A5 JP2001513765A5 (ja) | 2005-10-06 |
JP4155603B2 JP4155603B2 (ja) | 2008-09-24 |
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EP (1) | EP1032576B1 (ja) |
JP (1) | JP4155603B2 (ja) |
KR (1) | KR100542419B1 (ja) |
AU (1) | AU726375B2 (ja) |
BR (1) | BR9807790B1 (ja) |
CA (1) | CA2281860C (ja) |
DE (1) | DE69839020T2 (ja) |
TW (1) | TW425399B (ja) |
WO (1) | WO1998038195A1 (ja) |
ZA (1) | ZA981556B (ja) |
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WO2005014696A1 (ja) * | 2003-08-06 | 2005-02-17 | Mitsubishi Gas Chemical Company, Inc. | 光硬化性組成物及びコーティング剤組成物 |
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 |
JP2010523515A (ja) * | 2007-04-03 | 2010-07-15 | ビーエーエスエフ ソシエタス・ヨーロピア | 光活性窒素塩基 |
KR20110008186A (ko) * | 2008-03-31 | 2011-01-26 | 산아프로 가부시키가이샤 | 광염기 발생제 |
JP2013532223A (ja) * | 2010-06-30 | 2013-08-15 | スリーエム イノベイティブ プロパティズ カンパニー | オンデマンド型硬化性ポリシロキサンコーティング組成物 |
JP2013163670A (ja) * | 2012-01-11 | 2013-08-22 | Adeka Corp | 新規化合物及び感光性樹脂組成物 |
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1998
- 1998-02-14 KR KR1019997007769A patent/KR100542419B1/ko not_active IP Right Cessation
- 1998-02-14 DE DE69839020T patent/DE69839020T2/de not_active Expired - Lifetime
- 1998-02-14 AU AU64972/98A patent/AU726375B2/en not_active Ceased
- 1998-02-14 BR BRPI9807790-2A patent/BR9807790B1/pt not_active IP Right Cessation
- 1998-02-14 WO PCT/EP1998/000846 patent/WO1998038195A1/en active IP Right Grant
- 1998-02-14 CA CA002281860A patent/CA2281860C/en not_active Expired - Fee Related
- 1998-02-14 JP JP53724898A patent/JP4155603B2/ja not_active Expired - Fee Related
- 1998-02-14 EP EP98910669A patent/EP1032576B1/en not_active Expired - Lifetime
- 1998-02-25 ZA ZA981556A patent/ZA981556B/xx unknown
- 1998-03-10 TW TW087103457A patent/TW425399B/zh not_active IP Right Cessation
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Also Published As
Publication number | Publication date |
---|---|
JP4155603B2 (ja) | 2008-09-24 |
BR9807790A (pt) | 2000-02-15 |
DE69839020D1 (de) | 2008-03-06 |
BR9807790B1 (pt) | 2010-05-18 |
AU6497298A (en) | 1998-09-18 |
KR20000075701A (ko) | 2000-12-26 |
ZA981556B (en) | 1998-08-26 |
EP1032576A1 (en) | 2000-09-06 |
DE69839020T2 (de) | 2009-03-19 |
WO1998038195A1 (en) | 1998-09-03 |
TW425399B (en) | 2001-03-11 |
AU726375B2 (en) | 2000-11-02 |
CA2281860C (en) | 2007-04-10 |
KR100542419B1 (ko) | 2006-01-11 |
EP1032576B1 (en) | 2008-01-16 |
CA2281860A1 (en) | 1998-09-03 |
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