JP4485611B2 - 新規トリフェンジオキサジン化合物 - Google Patents
新規トリフェンジオキサジン化合物 Download PDFInfo
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- JP4485611B2 JP4485611B2 JP30143898A JP30143898A JP4485611B2 JP 4485611 B2 JP4485611 B2 JP 4485611B2 JP 30143898 A JP30143898 A JP 30143898A JP 30143898 A JP30143898 A JP 30143898A JP 4485611 B2 JP4485611 B2 JP 4485611B2
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- 150000001875 compounds Chemical class 0.000 title claims description 48
- -1 methoxyphenyl Chemical group 0.000 claims description 25
- 239000000049 pigment Substances 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 21
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 13
- 239000003086 colorant Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000000976 ink Substances 0.000 claims description 7
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical group C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000004040 coloring Methods 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 150000002829 nitrogen Chemical group 0.000 claims description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 239000003973 paint Substances 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- 229920001131 Pulp (paper) Polymers 0.000 claims description 2
- 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 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 239000004753 textile Substances 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 238000001035 drying Methods 0.000 description 10
- 239000012265 solid product Substances 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 125000003944 tolyl group Chemical group 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 239000004800 polyvinyl chloride Substances 0.000 description 4
- 229920000915 polyvinyl chloride Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 239000004743 Polypropylene Substances 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 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 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000004454 trace mineral analysis Methods 0.000 description 3
- XENRQAHMNIWSSC-UHFFFAOYSA-N 3-(4-methoxyphenyl)-1h-benzimidazol-2-one Chemical class C1=CC(OC)=CC=C1N1C(=O)NC2=CC=CC=C21 XENRQAHMNIWSSC-UHFFFAOYSA-N 0.000 description 2
- PBCALYKFBUDFDM-UHFFFAOYSA-N 3-(4-methylphenyl)-6-nitro-1h-benzimidazol-2-one Chemical compound C1=CC(C)=CC=C1N1C(=O)NC2=CC([N+]([O-])=O)=CC=C21 PBCALYKFBUDFDM-UHFFFAOYSA-N 0.000 description 2
- SMRULTWULHTNNR-UHFFFAOYSA-N 6-amino-3-(4-methylphenyl)-1h-benzimidazol-2-one Chemical compound C1=CC(C)=CC=C1N1C(=O)NC2=CC(N)=CC=C21 SMRULTWULHTNNR-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- RNXMAPTUJXBOFX-UHFFFAOYSA-N n-(4-methylphenyl)-2,4-dinitroaniline Chemical compound C1=CC(C)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O RNXMAPTUJXBOFX-UHFFFAOYSA-N 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NJVOHKFLBKQLIZ-UHFFFAOYSA-N (2-ethenylphenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1C=C NJVOHKFLBKQLIZ-UHFFFAOYSA-N 0.000 description 1
- 0 *c1ccccc1 Chemical compound *c1ccccc1 0.000 description 1
- SILNNFMWIMZVEQ-JZRMKITLSA-N 1,3-dihydrobenzimidazol-2-one Chemical class C1=CC=C2N[11C](=O)NC2=C1 SILNNFMWIMZVEQ-JZRMKITLSA-N 0.000 description 1
- HGEXWKZJLRGOOB-UHFFFAOYSA-N 1,3-dimethyl-5-nitrobenzimidazol-2-one Chemical compound C1=C([N+]([O-])=O)C=C2N(C)C(=O)N(C)C2=C1 HGEXWKZJLRGOOB-UHFFFAOYSA-N 0.000 description 1
- NOJXCBIUEXCLMZ-UHFFFAOYSA-N 1,3-dimethylbenzimidazol-2-one Chemical class C1=CC=C2N(C)C(=O)N(C)C2=C1 NOJXCBIUEXCLMZ-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- LXQOQPGNCGEELI-UHFFFAOYSA-N 2,4-dinitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O LXQOQPGNCGEELI-UHFFFAOYSA-N 0.000 description 1
- ZOZLYSQDLUDIJJ-UHFFFAOYSA-N 2,5-dichloro-3,6-bis(4-methoxy-n-(2-oxo-1,3-dihydrobenzimidazol-5-yl)anilino)cyclohexa-2,5-diene-1,4-dione Chemical compound C1=CC(OC)=CC=C1N(C=1C=C2NC(=O)NC2=CC=1)C1=C(Cl)C(=O)C(N(C=2C=CC(OC)=CC=2)C=2C=C3NC(=O)NC3=CC=2)=C(Cl)C1=O ZOZLYSQDLUDIJJ-UHFFFAOYSA-N 0.000 description 1
- ICAGWFAGIJDXAO-UHFFFAOYSA-N 2,5-dichloro-3,6-bis[(1,3-dimethyl-2-oxobenzimidazol-5-yl)amino]cyclohexa-2,5-diene-1,4-dione Chemical compound C1=C2N(C)C(=O)N(C)C2=CC(NC=2C(=O)C(Cl)=C(C(C=2Cl)=O)NC2=CC=C3N(C(N(C)C3=C2)=O)C)=C1 ICAGWFAGIJDXAO-UHFFFAOYSA-N 0.000 description 1
- CPBGCVJMGKQDAG-UHFFFAOYSA-N 2,5-dichloro-3,6-bis[[1-(4-methylphenyl)-2-oxo-3h-benzimidazol-5-yl]amino]cyclohexa-2,5-diene-1,4-dione Chemical compound C1=CC(C)=CC=C1N1C(=O)NC2=CC(NC=3C(C(Cl)=C(NC=4C=C5NC(=O)N(C=6C=CC(C)=CC=6)C5=CC=4)C(=O)C=3Cl)=O)=CC=C21 CPBGCVJMGKQDAG-UHFFFAOYSA-N 0.000 description 1
- CYKQHTZEPXKUOX-UHFFFAOYSA-N 2,5-dichloro-3-[(1-ethyl-2-oxo-3h-benzimidazol-5-yl)amino]-6-[(1-methyl-2-oxo-3h-benzimidazol-5-yl)amino]cyclohexa-2,5-diene-1,4-dione Chemical compound C1=C2N(C)C(=O)NC2=CC(NC=2C(=O)C(Cl)=C(C(C=2Cl)=O)NC2=CC=C3N(C(NC3=C2)=O)CC)=C1 CYKQHTZEPXKUOX-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- IPZPZSUDOPUDPM-UHFFFAOYSA-N 3,4-dinitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C([N+]([O-])=O)=C1 IPZPZSUDOPUDPM-UHFFFAOYSA-N 0.000 description 1
- FGAMQUWEVSYVPN-UHFFFAOYSA-N 3-(4-methoxyphenyl)-6-nitro-1h-benzimidazol-2-one Chemical compound C1=CC(OC)=CC=C1N1C(=O)NC2=CC([N+]([O-])=O)=CC=C21 FGAMQUWEVSYVPN-UHFFFAOYSA-N 0.000 description 1
- IICLMUUIBQONFI-UHFFFAOYSA-N 3-(4-methylphenyl)-1h-benzimidazol-2-one Chemical class C1=CC(C)=CC=C1N1C(=O)NC2=CC=CC=C21 IICLMUUIBQONFI-UHFFFAOYSA-N 0.000 description 1
- JHKRQZQRGCCWOO-UHFFFAOYSA-N 5-amino-1,3-dimethylbenzimidazol-2-one Chemical compound C1=C(N)C=C2N(C)C(=O)N(C)C2=C1 JHKRQZQRGCCWOO-UHFFFAOYSA-N 0.000 description 1
- GJXXUHGUCBUXSL-UHFFFAOYSA-N 5-amino-3h-1,3-benzoxazol-2-one Chemical compound NC1=CC=C2OC(=O)NC2=C1 GJXXUHGUCBUXSL-UHFFFAOYSA-N 0.000 description 1
- DLJZIPVEVJOKHB-UHFFFAOYSA-N 5-nitro-1,3-dihydrobenzimidazol-2-one Chemical compound [O-][N+](=O)C1=CC=C2NC(=O)NC2=C1 DLJZIPVEVJOKHB-UHFFFAOYSA-N 0.000 description 1
- OLSHHFCQRNBAAK-UHFFFAOYSA-N 6-amino-3-ethyl-1h-benzimidazol-2-one Chemical compound C1=C(N)C=C2NC(=O)N(CC)C2=C1 OLSHHFCQRNBAAK-UHFFFAOYSA-N 0.000 description 1
- MHEBKJBEJUTXJQ-UHFFFAOYSA-N 6-amino-3-methyl-1h-benzimidazol-2-one Chemical compound C1=C(N)C=C2NC(=O)N(C)C2=C1 MHEBKJBEJUTXJQ-UHFFFAOYSA-N 0.000 description 1
- STLPJYGZOIEDAJ-UHFFFAOYSA-N 6-amino-3h-1,3-benzoxazol-2-one Chemical compound NC1=CC=C2NC(=O)OC2=C1 STLPJYGZOIEDAJ-UHFFFAOYSA-N 0.000 description 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
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- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
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- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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- 230000015572 biosynthetic process Effects 0.000 description 1
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- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
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- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000002649 leather substitute Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- WRVHPSSSTBDGRK-UHFFFAOYSA-N sodium;sulfane;hydrate Chemical compound O.[Na].S WRVHPSSSTBDGRK-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000012463 white pigment Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B19/00—Oxazine dyes
- C09B19/02—Bisoxazines prepared from aminoquinones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paper (AREA)
- Coloring (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19747175.7 | 1997-10-24 | ||
| DE19747175A DE19747175A1 (de) | 1997-10-24 | 1997-10-24 | Chlorhaltige Triphendioxazin-Verbindungen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPH11335575A JPH11335575A (ja) | 1999-12-07 |
| JPH11335575A5 JPH11335575A5 (enExample) | 2005-12-08 |
| JP4485611B2 true JP4485611B2 (ja) | 2010-06-23 |
Family
ID=7846602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP30143898A Expired - Fee Related JP4485611B2 (ja) | 1997-10-24 | 1998-10-22 | 新規トリフェンジオキサジン化合物 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US6255482B1 (enExample) |
| EP (3) | EP0911337B1 (enExample) |
| JP (1) | JP4485611B2 (enExample) |
| DE (4) | DE19747175A1 (enExample) |
| ES (3) | ES2252106T3 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6617453B1 (en) | 1997-10-24 | 2003-09-09 | Clariant Finance (Bvi) Limited | Triphendioxazine compounds |
| DE19747175A1 (de) | 1997-10-24 | 1999-04-29 | Clariant Int Ltd | Chlorhaltige Triphendioxazin-Verbindungen |
| DE19913401A1 (de) * | 1999-03-25 | 2000-09-28 | Clariant Gmbh | Verfahren zur Herstellung von Dioxazin-Verbindungen |
| JP4526650B2 (ja) | 1999-04-22 | 2010-08-18 | クラリアント ファイナンス （ビーブイアイ） リミティド | 固溶体 |
| GB0002966D0 (en) * | 2000-02-10 | 2000-03-29 | Clariant Int Ltd | New triphendioxazine pigments |
| JP2001348499A (ja) * | 2000-03-06 | 2001-12-18 | Clariant Internatl Ltd | 顔料の調製 |
| DE10052221A1 (de) * | 2000-10-21 | 2002-05-02 | Clariant Gmbh | Verfahren zur Herstellung neuer Kristallmodifikationen eines methylsubstituierten Benzimidazolon-Dioxazin-Pigmentes |
| DE10052858A1 (de) | 2000-10-24 | 2002-04-25 | Clariant Gmbh | Mischkristalle aus Benzimidazolondioxazin-Verbindungen |
| JP4735792B2 (ja) * | 2001-09-27 | 2011-07-27 | 大日本印刷株式会社 | ジオキサジン系顔料を用いた着色レジスト組成物及びカラ−フィルター |
| DE102005024722A1 (de) * | 2005-05-31 | 2006-12-07 | Clariant Produkte (Deutschland) Gmbh | Blaues Farbmittel auf Basis von C.I. Pigment Blue 80 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR204531A1 (es) * | 1973-05-29 | 1976-02-12 | Ciba Geigy Ag | Pigmentos de iminoisoindolina y procedimiento para su preparacion |
| CH599299A5 (enExample) * | 1973-10-30 | 1978-05-31 | Ciba Geigy Ag | |
| DE2612391C2 (de) | 1976-03-24 | 1982-09-23 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von 5-Acetoacetylaminobenzimidazolon-(2) |
| DE2925541A1 (de) * | 1979-06-25 | 1981-01-22 | Hoechst Ag | 5-amino-benzimidazol-2-on-hydrat, verfahren zu seiner herstellung und seine verwendung als farbenvorprodukt |
| DE3010949A1 (de) | 1980-03-21 | 1981-10-01 | Cassella Ag, 6000 Frankfurt | Verbessertes verfahren zur herstellung eines violetten pigmentfarbstoffs |
| JPS5950260B2 (ja) | 1980-03-27 | 1984-12-07 | 住友化学工業株式会社 | ジオキサジン化合物の製法 |
| DE3125104A1 (de) * | 1981-06-26 | 1983-01-13 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von aryldiazosulfonaten |
| FR2515668A1 (fr) * | 1981-11-02 | 1983-05-06 | Sandoz Sa | Nouveaux composes dioxaziniques, leur preparation et leur utilisation comme pigments |
| EP0095255A3 (en) * | 1982-05-24 | 1984-02-29 | Imperial Chemical Industries Plc | Triphendioxazine dyes, methods for their manufacture and their use for dyeing cellulosic substrates |
| GB8421555D0 (en) * | 1984-08-24 | 1984-09-26 | Ici Plc | Water-soluble dye |
| DE3714288A1 (de) * | 1987-04-29 | 1988-11-10 | Bayer Ag | Fanalpigmente ringgeschlossener indamin- und diphenylmethanfarbstoffe enthaltende trockentoner |
| DE3917602A1 (de) * | 1989-05-31 | 1990-12-06 | Basf Ag | Verfahren zur herstellung von triphendioxazinen |
| FR2713234B1 (fr) | 1993-12-06 | 1996-03-22 | Sandoz Sa | Nouveaux dérivés de la triphénodioxazine, leur préparation et leur utilisation comme pigments. |
| DE4442291B4 (de) * | 1993-12-06 | 2006-04-13 | Clariant Finance (Bvi) Ltd. | Triphendioxazin-Verbindungen |
| DE59509166D1 (de) | 1994-02-04 | 2001-05-17 | Dystar Textilfarben Gmbh & Co | Wasserlösliche Azoverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbstoffe |
| DE4419849A1 (de) | 1994-06-07 | 1995-12-14 | Hoechst Ag | Isoindolinpigmente |
| PT765858E (pt) * | 1995-04-12 | 2000-05-31 | Ueno Seiyaku Oyo Kenkyujo Kk | Derivados naftol e processo para a producao dos mesmos |
| HRP960159A2 (en) | 1995-04-21 | 1997-08-31 | Bayer Ag | Benzocyclopentane oxazolidinones containing heteroatoms |
| DE19643344A1 (de) | 1996-10-21 | 1998-04-23 | Clariant Gmbh | Verfahren zur Herstellung von Dioxazin-Verbindungen |
| DE19727079A1 (de) | 1997-06-25 | 1999-01-07 | Clariant Int Ltd | Triphendioxazin |
| DE19747175A1 (de) | 1997-10-24 | 1999-04-29 | Clariant Int Ltd | Chlorhaltige Triphendioxazin-Verbindungen |
| EP0945455A1 (en) | 1998-03-26 | 1999-09-29 | Clariant Finance (BVI) Limited | Thriphendioxazine pigments |
-
1997
- 1997-10-24 DE DE19747175A patent/DE19747175A1/de not_active Withdrawn
-
1998
- 1998-10-19 US US09/175,139 patent/US6255482B1/en not_active Expired - Fee Related
- 1998-10-21 DE DE69829006T patent/DE69829006T2/de not_active Expired - Lifetime
- 1998-10-21 EP EP98811051A patent/EP0911337B1/en not_active Expired - Lifetime
- 1998-10-21 DE DE69811598T patent/DE69811598T2/de not_active Expired - Lifetime
- 1998-10-21 DE DE69833135T patent/DE69833135T2/de not_active Expired - Lifetime
- 1998-10-21 ES ES01110506T patent/ES2252106T3/es not_active Expired - Lifetime
- 1998-10-21 ES ES98811051T patent/ES2191919T3/es not_active Expired - Lifetime
- 1998-10-21 EP EP01110506A patent/EP1120420B1/en not_active Expired - Lifetime
- 1998-10-21 ES ES01110507T patent/ES2234728T3/es not_active Expired - Lifetime
- 1998-10-21 EP EP01110507A patent/EP1120421B1/en not_active Expired - Lifetime
- 1998-10-22 JP JP30143898A patent/JP4485611B2/ja not_active Expired - Fee Related
-
2000
- 2000-05-31 US US09/583,973 patent/US6355795B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1120420A2 (en) | 2001-08-01 |
| DE69811598D1 (de) | 2003-04-03 |
| JPH11335575A (ja) | 1999-12-07 |
| DE69833135T2 (de) | 2006-08-24 |
| EP0911337A1 (en) | 1999-04-28 |
| US6255482B1 (en) | 2001-07-03 |
| ES2234728T3 (es) | 2005-07-01 |
| DE69833135D1 (de) | 2006-04-06 |
| EP1120421A3 (en) | 2003-03-05 |
| ES2252106T3 (es) | 2006-05-16 |
| US6355795B1 (en) | 2002-03-12 |
| EP1120420A3 (en) | 2003-03-05 |
| EP1120420B1 (en) | 2006-01-11 |
| EP1120421A2 (en) | 2001-08-01 |
| DE69811598T2 (de) | 2003-09-25 |
| ES2191919T3 (es) | 2003-09-16 |
| DE69829006D1 (de) | 2005-03-17 |
| EP0911337B1 (en) | 2003-02-26 |
| EP1120421B1 (en) | 2005-02-09 |
| DE69829006T2 (de) | 2006-05-11 |
| DE19747175A1 (de) | 1999-04-29 |
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