DE19747175A1 - Chlorhaltige Triphendioxazin-Verbindungen - Google Patents
Chlorhaltige Triphendioxazin-VerbindungenInfo
- Publication number
- DE19747175A1 DE19747175A1 DE19747175A DE19747175A DE19747175A1 DE 19747175 A1 DE19747175 A1 DE 19747175A1 DE 19747175 A DE19747175 A DE 19747175A DE 19747175 A DE19747175 A DE 19747175A DE 19747175 A1 DE19747175 A1 DE 19747175A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- parts
- formula
- compounds
- hydrogen
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims description 76
- 239000000460 chlorine Substances 0.000 title claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 title claims description 5
- 229910052801 chlorine Inorganic materials 0.000 title claims description 5
- -1 alkyl radical Chemical class 0.000 claims description 34
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 18
- 239000000049 pigment Substances 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 9
- 150000003254 radicals Chemical class 0.000 claims description 9
- 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 9
- 239000003086 colorant Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 7
- 238000000576 coating method Methods 0.000 claims description 7
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 7
- 239000000976 ink Substances 0.000 claims description 5
- 229920003023 plastic Polymers 0.000 claims description 5
- 239000004033 plastic Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical compound 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
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 238000007363 ring formation reaction Methods 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000004753 textile Substances 0.000 claims description 3
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 claims description 2
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 claims description 2
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229920001131 Pulp (paper) Polymers 0.000 claims 1
- 238000004040 coloring Methods 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 20
- 238000001035 drying Methods 0.000 description 19
- 238000002844 melting Methods 0.000 description 18
- 230000008018 melting Effects 0.000 description 18
- 239000000843 powder Substances 0.000 description 18
- 238000009835 boiling Methods 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 7
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 125000003944 tolyl group Chemical group 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 239000004743 Polypropylene Substances 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 229920001155 polypropylene Polymers 0.000 description 5
- 239000001632 sodium acetate Substances 0.000 description 5
- 235000017281 sodium acetate Nutrition 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000005012 migration Effects 0.000 description 4
- 238000013508 migration Methods 0.000 description 4
- 239000004800 polyvinyl chloride Substances 0.000 description 4
- 229920000915 polyvinyl chloride Polymers 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000004575 stone Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 239000000706 filtrate Substances 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
- 239000013067 intermediate product Substances 0.000 description 3
- 238000004452 microanalysis Methods 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 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 2
- 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 2
- 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 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
- 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 2
- KCOMIGIXLPTNBH-UHFFFAOYSA-N 6-amino-3-(4-methoxyphenyl)-1h-benzimidazol-2-one Chemical compound C1=CC(OC)=CC=C1N1C(=O)NC2=CC(N)=CC=C21 KCOMIGIXLPTNBH-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- 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
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 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
- 239000012065 filter cake 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
- 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
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
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- 239000004814 polyurethane Substances 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- WRVHPSSSTBDGRK-UHFFFAOYSA-N sodium;sulfane;hydrate Chemical compound O.[Na].S WRVHPSSSTBDGRK-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 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
- 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
- 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
- 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
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- GJXXUHGUCBUXSL-UHFFFAOYSA-N 5-amino-3h-1,3-benzoxazol-2-one Chemical class 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
- OALYTRUKMRCXNH-UHFFFAOYSA-N 5-pentyloxolan-2-one Chemical compound CCCCCC1CCC(=O)O1 OALYTRUKMRCXNH-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 class NC1=CC=C2NC(=O)OC2=C1 STLPJYGZOIEDAJ-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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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- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
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- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
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- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
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- 238000004898 kneading Methods 0.000 description 1
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- 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
- 150000003901 oxalic acid esters Chemical class 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 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
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- 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
- 206010037844 rash Diseases 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000126 substance Substances 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
- 150000003673 urethanes Chemical class 0.000 description 1
- 239000002966 varnish Substances 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)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19747175A DE19747175A1 (de) | 1997-10-24 | 1997-10-24 | Chlorhaltige Triphendioxazin-Verbindungen |
| US09/175,139 US6255482B1 (en) | 1997-10-24 | 1998-10-19 | Triphendioxazine compounds |
| EP98811051A EP0911337B1 (en) | 1997-10-24 | 1998-10-21 | Process for the preparation of triphendioxazine compounds |
| DE69829006T DE69829006T2 (de) | 1997-10-24 | 1998-10-21 | Triphendioxazinverbindungen |
| ES98811051T ES2191919T3 (es) | 1997-10-24 | 1998-10-21 | Procedimiento para la preparacion de compuestos de trifendioxazina. |
| DE69811598T DE69811598T2 (de) | 1997-10-24 | 1998-10-21 | Verfahren zur Herstellung von Triphendioxazinverbindungen |
| EP01110506A EP1120420B1 (en) | 1997-10-24 | 1998-10-21 | Triphendioxazine compounds |
| ES01110506T ES2252106T3 (es) | 1997-10-24 | 1998-10-21 | Nuevos compuestos de trifendioxazina. |
| DE69833135T DE69833135T2 (de) | 1997-10-24 | 1998-10-21 | Triphendioxazinverbindungen |
| EP01110507A EP1120421B1 (en) | 1997-10-24 | 1998-10-21 | New triphendioxazine compounds |
| ES01110507T ES2234728T3 (es) | 1997-10-24 | 1998-10-21 | Nuevos compuestos de trifendioxazina. |
| JP30143898A JP4485611B2 (ja) | 1997-10-24 | 1998-10-22 | 新規トリフェンジオキサジン化合物 |
| US09/583,973 US6355795B1 (en) | 1997-10-24 | 2000-05-31 | Triphendioxazine compounds |
| US09/718,278 US6617453B1 (en) | 1997-10-24 | 2000-11-22 | Triphendioxazine compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19747175A DE19747175A1 (de) | 1997-10-24 | 1997-10-24 | Chlorhaltige Triphendioxazin-Verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19747175A1 true DE19747175A1 (de) | 1999-04-29 |
Family
ID=7846602
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19747175A Withdrawn DE19747175A1 (de) | 1997-10-24 | 1997-10-24 | Chlorhaltige Triphendioxazin-Verbindungen |
| DE69829006T Expired - Lifetime DE69829006T2 (de) | 1997-10-24 | 1998-10-21 | Triphendioxazinverbindungen |
| DE69811598T Expired - Lifetime DE69811598T2 (de) | 1997-10-24 | 1998-10-21 | Verfahren zur Herstellung von Triphendioxazinverbindungen |
| DE69833135T Expired - Lifetime DE69833135T2 (de) | 1997-10-24 | 1998-10-21 | Triphendioxazinverbindungen |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69829006T Expired - Lifetime DE69829006T2 (de) | 1997-10-24 | 1998-10-21 | Triphendioxazinverbindungen |
| DE69811598T Expired - Lifetime DE69811598T2 (de) | 1997-10-24 | 1998-10-21 | Verfahren zur Herstellung von Triphendioxazinverbindungen |
| DE69833135T Expired - Lifetime DE69833135T2 (de) | 1997-10-24 | 1998-10-21 | Triphendioxazinverbindungen |
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 |
Citations (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2425594A1 (de) * | 1973-05-29 | 1974-12-19 | Ciba Geigy Ag | Iminoisoindolinpigmente und verfahren zu deren herstellung |
| DE2451097A1 (de) * | 1973-10-30 | 1975-05-07 | Ciba Geigy Ag | Disazopigmente, verfahren zu deren herstellung und verwendung |
| 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 |
| DE2612391C2 (de) * | 1976-03-24 | 1982-09-23 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von 5-Acetoacetylaminobenzimidazolon-(2) |
| EP0095255A2 (en) * | 1982-05-24 | 1983-11-30 | Imperial Chemical Industries Plc | Triphendioxazine dyes, methods for their manufacture and their use for dyeing cellulosic substrates |
| US4515940A (en) * | 1981-06-26 | 1985-05-07 | Hoechst Aktiengesellschaft | Process for the preparation of aryldiazosulfonates |
| US4738721A (en) * | 1984-08-24 | 1988-04-19 | Canon Kabushiki Kaisha | Ink comprising a water-soluble triphendioxazine dye |
| US4869989A (en) * | 1987-04-29 | 1989-09-26 | Bayer Aktiengesellschaft | Dry toners containing fanal pigments based on cationic dyes |
| DE3917602A1 (de) * | 1989-05-31 | 1990-12-06 | Basf Ag | Verfahren zur herstellung von triphendioxazinen |
| GB2284427A (en) * | 1993-12-06 | 1995-06-07 | Sandoz Ltd | Triphendioxazine compounds |
| DE4442291A1 (de) * | 1993-12-06 | 1995-06-08 | Sandoz Ag | Triphendioxazin-Verbindungen |
| EP0675172A2 (de) * | 1994-02-04 | 1995-10-04 | Hoechst Aktiengesellschaft | Wasserlösliche Azoverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbstoffe |
| EP0686673A1 (de) * | 1994-06-07 | 1995-12-13 | Hoechst Aktiengesellschaft | Isoindolinpigmente |
| WO1996032366A1 (en) * | 1995-04-12 | 1996-10-17 | Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo | Naphthol derivatives and process for producing the same |
| EP0738726A1 (de) * | 1995-04-21 | 1996-10-23 | Bayer Ag | Heteroatomhaltige Benzocyclopentanoxazolidinone mit antibakteriellen Wirkung |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| FR2515668A1 (fr) * | 1981-11-02 | 1983-05-06 | Sandoz Sa | Nouveaux composes dioxaziniques, leur preparation et leur utilisation comme pigments |
| 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
Patent Citations (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2425594A1 (de) * | 1973-05-29 | 1974-12-19 | Ciba Geigy Ag | Iminoisoindolinpigmente und verfahren zu deren herstellung |
| DE2451097A1 (de) * | 1973-10-30 | 1975-05-07 | Ciba Geigy Ag | Disazopigmente, verfahren zu deren herstellung und verwendung |
| 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 |
| US4515940A (en) * | 1981-06-26 | 1985-05-07 | Hoechst Aktiengesellschaft | Process for the preparation of aryldiazosulfonates |
| EP0095255A2 (en) * | 1982-05-24 | 1983-11-30 | Imperial Chemical Industries Plc | Triphendioxazine dyes, methods for their manufacture and their use for dyeing cellulosic substrates |
| US4738721A (en) * | 1984-08-24 | 1988-04-19 | Canon Kabushiki Kaisha | Ink comprising a water-soluble triphendioxazine dye |
| US4869989A (en) * | 1987-04-29 | 1989-09-26 | Bayer Aktiengesellschaft | Dry toners containing fanal pigments based on cationic dyes |
| DE3917602A1 (de) * | 1989-05-31 | 1990-12-06 | Basf Ag | Verfahren zur herstellung von triphendioxazinen |
| GB2284427A (en) * | 1993-12-06 | 1995-06-07 | Sandoz Ltd | Triphendioxazine compounds |
| DE4442291A1 (de) * | 1993-12-06 | 1995-06-08 | Sandoz Ag | Triphendioxazin-Verbindungen |
| CH688237A5 (de) * | 1993-12-06 | 1997-06-30 | Clariant Finance Bvi Ltd | Triphendioxazin-Verbindungen. |
| EP0675172A2 (de) * | 1994-02-04 | 1995-10-04 | Hoechst Aktiengesellschaft | Wasserlösliche Azoverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbstoffe |
| EP0686673A1 (de) * | 1994-06-07 | 1995-12-13 | Hoechst Aktiengesellschaft | Isoindolinpigmente |
| WO1996032366A1 (en) * | 1995-04-12 | 1996-10-17 | Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo | Naphthol derivatives and process for producing the same |
| EP0738726A1 (de) * | 1995-04-21 | 1996-10-23 | Bayer Ag | Heteroatomhaltige Benzocyclopentanoxazolidinone mit antibakteriellen Wirkung |
Non-Patent Citations (6)
| Title |
|---|
| Chem.Abstract 95-23-8 und 73778-92-4 * |
| Chem.Abstract,Reg.-Nr. 6973-93-9,123855-79-8, 76097-86-4,16117-48-0 * |
| Chemical Abstracts: Vol. 72, 1970, Ref. 31697y * |
| Chemical Abstracts: Vol. 92, 1980, Ref. 215441e * |
| Chemical Abstracts: Vol. 96, 1982, Ref. 218731t * |
| Derwent Abstracts, Ref. 83-726920/31 zu RESEARCH DISCLOSURE Vol. 231 Nr. 009 (1999). * |
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 |
| JP4485611B2 (ja) | 2010-06-23 |
| 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 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OM8 | Search report available as to paragraph 43 lit. 1 sentence 1 patent law | ||
| 8130 | Withdrawal |