CN1113506A - 含有羟基吡啶酮偶合组分的双酸性偶氮染料及其中间体 - Google Patents
含有羟基吡啶酮偶合组分的双酸性偶氮染料及其中间体 Download PDFInfo
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- CN1113506A CN1113506A CN95106501A CN95106501A CN1113506A CN 1113506 A CN1113506 A CN 1113506A CN 95106501 A CN95106501 A CN 95106501A CN 95106501 A CN95106501 A CN 95106501A CN 1113506 A CN1113506 A CN 1113506A
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- diazo component
- azoic dyestuff
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- 239000002253 acid Substances 0.000 title claims abstract description 13
- 238000005859 coupling reaction Methods 0.000 title abstract description 8
- 230000008878 coupling Effects 0.000 title abstract description 7
- 238000010168 coupling process Methods 0.000 title abstract description 7
- 239000000987 azo dye Substances 0.000 title abstract description 3
- 239000000543 intermediate Substances 0.000 title description 2
- GGOZGYRTNQBSSA-UHFFFAOYSA-N pyridine-2,3-diol Chemical class OC1=CC=CN=C1O GGOZGYRTNQBSSA-UHFFFAOYSA-N 0.000 title description 2
- 239000000975 dye Substances 0.000 claims abstract description 32
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims abstract description 12
- 238000004043 dyeing Methods 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 238000007639 printing Methods 0.000 claims abstract description 3
- 239000000758 substrate Substances 0.000 claims abstract description 3
- -1 aromatic heterocycle amine Chemical class 0.000 claims description 58
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 10
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 10
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 9
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical class C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 6
- DYUMBFTYRJMAFK-UHFFFAOYSA-N 3-cyano-2-pyridone Chemical compound OC1=NC=CC=C1C#N DYUMBFTYRJMAFK-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000003851 azoles Chemical class 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 3
- 229930192474 thiophene Natural products 0.000 claims description 3
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 claims description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
- QPQKUYVSJWQSDY-UHFFFAOYSA-N 4-phenyldiazenylaniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=CC=C1 QPQKUYVSJWQSDY-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- 150000002240 furans Chemical class 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 150000002460 imidazoles Chemical class 0.000 claims description 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
- 239000006225 natural substrate Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 150000003217 pyrazoles Chemical class 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 150000003233 pyrroles Chemical class 0.000 claims description 2
- 150000004867 thiadiazoles Chemical class 0.000 claims description 2
- RBRCCWBAMGPRSN-UHFFFAOYSA-N thieno[2,3-d][1,3]thiazole Chemical class S1C=NC2=C1C=CS2 RBRCCWBAMGPRSN-UHFFFAOYSA-N 0.000 claims description 2
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 claims description 2
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 claims description 2
- RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical compound C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 claims description 2
- WHLUQAYNVOGZST-UHFFFAOYSA-N tifenamil Chemical group C=1C=CC=CC=1C(C(=O)SCCN(CC)CC)C1=CC=CC=C1 WHLUQAYNVOGZST-UHFFFAOYSA-N 0.000 claims description 2
- 150000003852 triazoles Chemical class 0.000 claims description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 1
- KASRJFLYQIMFKD-UHFFFAOYSA-N 2-oxo-1h-pyridine-3-sulfonic acid Chemical class OS(=O)(=O)C1=CC=CNC1=O KASRJFLYQIMFKD-UHFFFAOYSA-N 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000243 solution Substances 0.000 description 14
- 239000001257 hydrogen Substances 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 125000004093 cyano group Chemical group *C#N 0.000 description 10
- 150000002431 hydrogen Chemical class 0.000 description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
- 229930194542 Keto Natural products 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 6
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 125000001544 thienyl group Chemical group 0.000 description 4
- 210000002268 wool Anatomy 0.000 description 4
- 235000005979 Citrus limon Nutrition 0.000 description 3
- 244000248349 Citrus limon Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 3
- 229920002292 Nylon 6 Polymers 0.000 description 3
- BDKZHNJTLHOSDW-UHFFFAOYSA-N [Na].CC(O)=O Chemical compound [Na].CC(O)=O BDKZHNJTLHOSDW-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 description 2
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000001118 alkylidene group Chemical group 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 235000011167 hydrochloric acid Nutrition 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- JIQNWFBLYKVZFY-UHFFFAOYSA-N methoxycyclohexatriene Chemical compound COC1=C[C]=CC=C1 JIQNWFBLYKVZFY-UHFFFAOYSA-N 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
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- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
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- 125000001424 substituent group Chemical group 0.000 description 2
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- JSLZUBLGGPEVQN-DIPNUNPCSA-N (2r)-4-methyl-2-propan-2-yl-2-[2-[4-[4-[2-(3,4,5-trimethoxyphenyl)ethyl]piperazin-1-yl]butoxy]phenyl]-1,4-benzothiazin-3-one Chemical compound COC1=C(OC)C(OC)=CC(CCN2CCN(CCCCOC=3C(=CC=CC=3)[C@@]3(C(N(C)C4=CC=CC=C4S3)=O)C(C)C)CC2)=C1 JSLZUBLGGPEVQN-DIPNUNPCSA-N 0.000 description 1
- 125000004758 (C1-C4) alkoxyimino group Chemical group 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- WIHIUTUAHOZVLE-UHFFFAOYSA-N 1,3-diethoxypropan-2-ol Chemical compound CCOCC(O)COCC WIHIUTUAHOZVLE-UHFFFAOYSA-N 0.000 description 1
- HRMGYAZODUDKFX-UHFFFAOYSA-N 1-$l^{1}-oxidanylsulfonyl-4-methylbenzene Chemical compound CC1=CC=C(S([O])(=O)=O)C=C1 HRMGYAZODUDKFX-UHFFFAOYSA-N 0.000 description 1
- CRTIGUQLTBDWKN-UHFFFAOYSA-N 1-aminocyclohexa-2,4-diene-1-sulfonic acid Chemical compound OS(=O)(=O)C1(N)CC=CC=C1 CRTIGUQLTBDWKN-UHFFFAOYSA-N 0.000 description 1
- QTLDSJXCGIKEJJ-UHFFFAOYSA-N 2-(ethylamino)benzonitrile Chemical compound CCNC1=CC=CC=C1C#N QTLDSJXCGIKEJJ-UHFFFAOYSA-N 0.000 description 1
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- HWXWPZQREZOXJJ-UHFFFAOYSA-N 3-(ethylamino)benzonitrile Chemical compound CCNC1=CC=CC(C#N)=C1 HWXWPZQREZOXJJ-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- PMZBHPUNQNKBOA-UHFFFAOYSA-N 5-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=CC(C(O)=O)=CC(C(O)=O)=C1 PMZBHPUNQNKBOA-UHFFFAOYSA-N 0.000 description 1
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 1
- NQRLWRODNCDUHY-UHFFFAOYSA-N 6-n,6-n,2-trimethylacridine-3,6-diamine Chemical compound C1=C(C)C(N)=CC2=NC3=CC(N(C)C)=CC=C3C=C21 NQRLWRODNCDUHY-UHFFFAOYSA-N 0.000 description 1
- AWMHRVHGKOFCNI-UHFFFAOYSA-N C(CCCC)OC(C(C)(C)C)OOCCC(C)C Chemical compound C(CCCC)OC(C(C)(C)C)OOCCC(C)C AWMHRVHGKOFCNI-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 235000005976 Citrus sinensis Nutrition 0.000 description 1
- 240000002319 Citrus sinensis Species 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 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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- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229950001891 iprotiazem Drugs 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
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- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
- C09B33/12—Disazo dyes in which the coupling component is a heterocyclic compound
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
- C07D213/71—Sulfur atoms to which a second hetero atom is attached
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- 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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/18—Trisazo or higher polyazo dyes
- C09B33/28—Tetrazo dyes of the type A->B->K<-C<-D
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Abstract
Description
本发明涉及通式(Ⅰ)的以游离酸或其盐形式的新颖的偶氮染料:
式中D是重氮组分,而
X是用或不用醚官能中的氧原子所隔开的C2-C8亚烷基。
本发明也涉及它们在染色或印染天然基质物或合成基质物方面的用途,涉及作为这些染料的偶合组分的磺基吡啶酮类及它们的制法。
本发明的一个目的就是提供一类新颖的偶氮染料,它们含有作为偶合组分的双倍的3-羟基磺酰基-4-甲基-6-羟吡啶-2-酮,并具有优越的应用性能。
我们业已发现,使用上面定义的通式Ⅰ的偶氮染料,这一目的可以达到。
通式Ⅰ的新颖偶氮染料可以以游离酸形式存在,也可以其盐的形式存在。
合适的盐是金属盐或铵盐。金属盐特别包括锂盐,钠盐或钾盐。为此发明目的的铵盐是含已取代或未取代铵阳离子的铵盐。已取代铵阳子包括:例如,一烷基,二烷基,三烷基,四烷基或苄基三烷基铵阳离子,或来自含氮五元或六元饱和杂环的铵阳离子,例如吡咯烷鎓,哌嗪鎓,吗啉鎓,哌嗪鎓,或N-烷基哌嗪鎓阳离子,或它们的N-单烷基或N,N-二烷基的取代产物。为此发明目的的烷基通常是直链的或支化的C1-C20烷基,此烷基可以被羟基取代和/或可以被醚官能中的1-4个氧原子所隔开。
出现在上述通式的任何烷基或亚烷基可以是直链的或支化的。
X例如是CH2,(CH2)2,(CH2)3,(CH2)4,CH2)5,CH(2)6,(CH2)7,(CH2)8,CH(CH3)CH2,CH(CH3)CH(CH3),C2H4OC2H4,C3H6OC2H4,C3H6OC3H6,C4H8OC3H6,or C4H8OC4H8,
通式Ⅰ偶氮染料中重要的是其中的D是来自苯胺,来自氨基萘或来自五元芳族杂环胺的重氮组份基团,此杂环胺含有1-3个选自杂环中的氮、氧和硫的杂原子,此杂环带有或不带有稠含在其上的苯环、噻吩环、吡啶环或嘧啶环。
通式Ⅰ的重要偶氮染料是那么一类,其中,D是来自苯胺,来自氨基萘或来自杂环胺的重氮组分基团,该杂环胺是吡咯,呋喃,噻吩,吡唑,咪唑,¥唑,异¥唑,噻唑,异噻唑,三唑,¥二唑,噻二唑,苯并呋喃,苯并噻吩,苯并咪唑,苯并¥唑,苯并噻唑,苯并异噻唑,吡啶并噻吩,嘧啶并噻吩,噻吩并噻吩,或噻吩并噻唑系列的杂环胺。
通式Ⅰ偶氮染料中特别重要的是D是来自苯胺,来自氨基萘的重氮组分基团,而来自苯胺的是特别重要的。
通式Ⅰ偶氮染料中具有工业重要性的是其中D是来自氨基二苯甲酮,来自氨基偶氮苯或来自氨基苯甲酸。
D基团符合例如下面的通式的重氮组分基团:
式中
L1是硝基,氰基,C1-C6链烷酰基,苯甲酰基,C1-C6烷基磺酰基,已取代或未取代的苯磺酰基,或通式-CH=T的基团,式中,T是羟亚氨基,C1-C4烷氧亚氨基,或酸性CH化合物的基团,
L2是氢,C1-C6烷基,卤素,羟基,巯基,未取代的或被苯基或C1-C4烷氧基取代的C1-C6烷氧基,已取代的或未取代的苯氧基,未取代的或被苯基取代的C1-C6烷硫基,已取代的或未取代的苯硫基,C1-C6烷基磺酰基,或者已取代的或未取代的苯基磺酰基,
L3是氰基,C1-C4烷氧羰基,羧基或硝基,
L4是氢,C1-C6烷基或苯基,
L5是C1-C6烷基或苯基,
L6是氢,氰基,C1-C4烷氧羰基,羧基,C1-C6链烷酰基,氰硫基或卤素
L7是硝基,氰基,C1-C6链烷酰基,苯甲酰基,C1-C4烷氧羰基,羧基,C1-C6烷基磺酰基,已取代的或未取代的苯磺酰基或通式为-CH=T的基团,式中T如上面所定义。
L8是氢,C1-C6烷基,氰基,卤素,未取代的或被苯基或C1-C4烷氧基取代的C1-C6烷氧基,未取代的或被苯基取代的C1-C6烷硫基,已取代的或未取代的苯硫基,C1-C6烷基磺酰基,已取代的或未取代的苯磺酰基,C1-C4烷氧羰基或羧基,
L9是氰基,未取代的或被苯基取代的C1-C6烷基,未取代的或被苯基取代的C1-C6烷硫基,已取代的或未取代的苯基,噻吩基,C1-C4烷基噻吩基,吡啶基,或C1-C4烷基吡啶基,
L10是苯基或吡啶基,
L11是三氟甲基,硝基,C1-C6烷基,苯基,未取代或被苯基取代的C1-C6烷硫基或二(C1-C6烷基)氨基,
L12是C1-C6烷基,苯基,2-氰乙硫基或2-(C1-C6烷氧羰基)乙硫基,
L13是氢,硝基或卤素,
L14是氢,氰基,C1-C4烷氧羰基,羧基,硝基或卤素,
L15和L16彼此相同或不同,而且每个独立地是氢,C1-C6烷基,C1-C6烷氧基或卤素,
L17是氢,C1-C6烷基,三氟甲基,C1-C6链烷酰基,取代的或未取代的苯甲酰基,C1-C4烷氧羰基,羟磺酰基,已取代或未取代的苯磺酰氧基,单-或双(C1-C4烷基)氨基甲酰基,单-或双(C1-C4烷基)氨基磺酰基,C1-C4链烷酰氨基,羟磺酰基,或羧苯基偶氮基,5-(C1-C4烷基)-1,2,4-¥二唑-3-基,或6-羟磺酰基-7-甲基苯并噻唑-2-基,以及
环A有一个稠合在其上的苯环或羟磺酰苯环。
任何出现在上述通式中的烷基或亚烷基可以是直链的或支化的。
任何出现在上述偶氮染料通式中的已取代苯基可含有例如C1-C4烷基,氯,溴,硝基或C1-C4烷氧基作为取代基。在已取代苯基中的取代基的数目通常为1-3。
在已取代烷基中的取代基的数目通常是1或2。
L2,L4,L5,L8,L9,L11,L12,L15,L16和L17每个例如是甲基,乙基,丙基,异丙基,丁基,异丁基,仲丁基,戊基,异戊基,新戊基,叔戊基,己基或2-甲基戊基。
L9也可以例如是苄基,或1-或2-苯乙基。
L2,L8,L9和L11每个也可以例如是甲硫基,乙硫基,丙硫基,异丙硫基,丁硫基,异丁硫基,戊硫基,己硫基,苄硫基,或1-或2-苯乙硫基。
L2和L8每个也可以例如是苯硫基,2-甲基苯硫基,2-甲氧基苯硫基,或2-氯代苯硫基。
L2,L8,L15和L16每个也可以例如是甲氧基,乙氧基,丙氧基,异丙氧基,丁氧基,异丁氧基,仲-丁氧基,戊氧基,异戊氧基,新戊氧基,叔戊氧基,己氧基,或2-甲基戊氧基。
L2,L8,L13,L14,L15和L16每个可以例如是氟,氯或溴。
L7,以及L1,L2,L8例如是甲基磺酰基,乙基磺酰基,丙基磺酰基,异丙基磺酰基,丁基磺酰基,异丁基磺酰基,仲丁基磺酰基,戊基磺酰基,异戊基磺酰基,新戊基磺酰基,己基磺酰基,苯磺酰基,2-甲基苯磺酰基,2-甲氧基苯磺酰基,或2-氯代苯磺酰基。
L3,以及L6,L7,L8,L14和L17例如是甲氧羰基,乙氧羰基,丙氧羰基,异丙氧羰基,丁氧羰基,异丁氧羰基,或仲丁氧羰基。
L2和L8每个也可以例如是2-甲氧乙氧基,2-乙氧乙氧基,2-或3-甲氧丙氧基,2-或3-乙氧丙氧基,2-或4-甲氧丁氧基,2-或4-乙氧丁氧基,5-甲氧戊氧基,5-乙氧戊氧基,6-甲氧己氧基,6-乙氧己氧基,苄氧基,或1-或2-苯乙氧基。
L11也可以例如是二甲氨基,二乙氨基,二丙氨基,二异丙氨基,二丁氨基,二戊氨基,二己氨基,或N-甲基-N-乙基氨基。
L12也可以例如是2-甲氧羰基乙硫基,或2-乙氧羰基乙硫基。
L9也可以例如是苯基,2-,3-或4-甲基苯基,2,4-二甲基苯基,2-,3-或4-甲氧苯基,2-,3-或4-氯代苯基,2-,3-或4-甲氧苯基,2-,3-或4-甲基噻吩基,或2-,3-或4-甲基吡啶基。
L1,L6,L7和L17每个也可以例如是甲酰基,乙酰基,丙酰基,丁酰基,戊酰基或己酰基。
L17也可以例如是苯甲酰基,2-,3-或4-甲基苯甲酰基,2-,3-或4-乙基苯甲酰基,2-,3-或4-丙基苯甲酰基,2-,3-或4-异丙基苯甲酰基,2,3-,2,4-,2,5-,2,6-,3,4-或3,5-二甲基苯甲酰基,2-甲基-4-甲氧基苯甲酰基,2-,3-或4-甲氧基苯甲酰基,2-,3-或4-乙氧基苯甲酰基,苯磺酰氧基,2-,3-或4-甲基苯磺酰氧基,单-或二-甲基氨基甲酰基,单-或二-乙基氨基甲酰基,单-或二-丙基氨基甲酰基,单-或二-异丙基氨基甲酰基,单-或二-丁基氨基甲酰基,单-或二-甲基氨基磺酰基,单-或二-乙基氨基磺酰基,单-或二-丙基氨基磺酰基,单-或二-异丙基氨基磺酰基,单-或二丁基氨基磺酰基,甲酰氨基,乙酰氨基,丙酰氨基,丁酰氨基,异丁酰氨基,4-羟磺酰苯基偶氮基,4-羧苯基偶氮基,5-甲基-1,2,4-¥二唑-3-基,或5-乙基-1,2,4-¥二唑-3-基。
当L1或L7是-CH=T基(式中的T来自酸性CH化合物H2T)时,合适的酸性CH化合物H2T包括例如下列通式的化合物:
Z1是氰基,硝基,C1-C4链烷酰基,已取代的或未取代的苯甲酰基,C1-C4烷基磺酰基,已取代的或未取代的苯磺酰基。羧基,C1-C4烷氧羰基,C3-C4链烯氧羰基,苯氧羰基,氨基甲酰基,单-或二(C1-C4烷基)氨基甲酰基,已取代或未取代的苯氨基甲酰基,已取代或未取代的苯基,苯并噻唑-2-基,苯并咪唑-2-基,5-苯基-1,3,4-噻二唑-2-基,或2-hydroxychinoxalin-3-YL。
Z2是C1-C4烷基,C1-C4烷氧基,或C3-C4链烯氧基。
Z3是C1-C4烷氧羰基,C3-C4链烯氧羰基,苯基氨基甲酰基,或苯并咪唑-2-基,
Z4是氰基,C1-C4烷氧羰基,C3-C4链烯氧羰基,
Z5是氢或C1-C6烷基,
Z6是氢,C1-C4烷基或苯基,以及
Z7是C1-C4烷基。
注意来自通式Ⅲa,Ⅲb或Ⅲc化合物的基团,而Ⅲa,Ⅲb或Ⅲc中的Z1是氰基,C1-C4链烷酰基,C1-C4烷氧羰基,或C3-C4链烯氧羰基,Z2是C1-C4烷基,C1-C4烷氧基,或C3-C4链烯氧基,Z3是C1-C4烷氧羰基,或C3-C4链烯氧羰基,以及Z4是氰基。
要特别注意来自通式Ⅲa,Ⅲb或Ⅲc化合物的基团,式中Ⅲa,Ⅲb或Ⅲc中的Z1是氰基,C1-C4烷氧羰基,或C3-C4链烯氧羰基,Z2是C1-C4烷氧基,或C2-C4链烯氧基,Z3是C1-C4烷氧羰基,或C3-C4链烯氧羰基,以及Z4是氰基。
优选通式Ⅰa的偶氮染料
式中L15,L16,L17,X和环A每个如上面所定义。
特别优选通式Ⅰb的偶氮染料
式中,X如上面所定义,L15和L16每个是氢,而L17是已取代或未取代的苯甲酰基,或者L15和L16彼此独立地是氢,C1-C4烷基,或C1-C4烷氧基,而L17是羟磺酰基苯基偶氮基或羧苯基偶氮基。
还要特别注意通式Ⅰc的偶氮染料
式中,Z1和Z2中的一个是氢,而另一个是C1-C4烷氧羰基,而X如上面所定义。
根据本发明的通式(Ⅰ)的偶氮染料可以用通常方法来获得,例如将通式Ⅳ的胺进行重氮化
式中,D如上面所定义,并用通式Ⅴ的磺基吡啶酮与所得的重氮盐进行偶合反应,
,式中的X如上面所定义。
本发明还以游离酸或其盐的形式提供通式Ⅴ的磺基吡啶酮
式中X是C2-C8亚烷基,它用或不用醚官能团中的氧原子隔开。
本发明还提供通式Ⅴ的磺基吡啶酮的优异制法,此制法包括,在浓硫酸中在80-130℃处理通式Ⅵ的氰基吡啶酮
,式中的X如上面所定义。
此新颖制法优选在90-125℃下进行。
为此发明目的的浓硫酸是重量浓度为96-98%的硫酸,通常,相对于每一重量份的氰基吡啶酮使用2-2.5重量份的浓硫酸。
此新颖制法通常以开始时加入浓硫酸并在室温下将氰基吡啶酮Ⅵ加至浓硫酸中而进行。温度将升高并使之升至约60-70℃。随后在本发明的温度下搅拌一段时间。5-8小时后反应通常将结束,然后将反应混合物冷却。然后可将它加至冰-水混合物中,并进行中和。如此得到的溶液可直接用于制造通式Ⅰ的偶氮染料。
存在少量三氧化硫是会有好处的,在此情况下,反应介质是例如重量浓度为2-5%的发烟硫酸。
根据本发明的通式Ⅰ偶氮染料优异的适用于天然的合成的基质物,例如羊毛、革或聚酰胺的染色。所获得的染色具有良好的全面牢度。
下面的实施例解说本发明。
实施例1
将163克下式的氰基吡啶酮
加至40克发烟硫酸(重量浓度24%)与380克硫酸(重量浓度100%)的混合物中。让温度从开始加入时的15℃升至最高值70℃。将混合物在70至80℃搅拌2小时,然后加热至90℃以便放出CO2。随后以能够控制CO2的放出的方式将反应温度在约4小时内升至130-135℃,接着在130-135℃再搅拌6小时。把冷却下得到的熔融物在搅拌下倒入约1000克冰和500毫升水中,并将所得的沉淀用氢氧化钠溶液调节至PH7,并同时冷却至<40℃。所得到的产物是如下通式的磺基吡啶酮的清亮溶液(在放置时它能沉淀硫酸钠)。
实施例2
将340克下式的氰基吡啶酮
加至760克硫酸(重量浓度为100%)和80克发烟硫酸(重量浓度为24%)的混合物中,并如实施例1所述的进行反应。得到了以水溶液的形式的0.97摩尔其通式如下的磺基吡啶酮
实施例3
将30克4-氨基-4-甲基二苯甲酮盐酸盐在搅拌下加入到55毫升重量浓度为17%的盐酸中。然后将混合物冷却至0℃,将40克冰,同时也将20毫升重量浓度为23%的亚硝酸钠水溶液加入,加入时,重氮化物料的温度不能超过10℃。随后把物料再搅拌1小时,而同时用冰把它冷至0-5℃。在过量的亚硝酸被破坏之后,在<0℃下用少量乙酸钠和氢氧化钠溶液将所得到的重氮盐溶液的PH升至5-6。然后,将如下通式的磺基吡啶酮14.85克
以水溶液的形式在20分钟内加入,而同时加入氢氧化钠溶液并使PH值维持在4-7.5的范围内。
下式的染料
以结晶沉淀的形式沉淀出来,并用盐析法在PH值为7下使此染料以二钠盐的形式分离出来。经干燥得45克黄色粉末,它在水中生成黄色溶液。以通常的染色法用0.8克这种染料对100克复鞣铬鞣牛皮皮革进行染色,生成带鲜明色调的深柠檬黄表面染色。
聚己内酰胺织物被用通常染色法染成鲜明的深柠檬黄色调,而羊毛被染成深的中性黄色调。
实施例4
用实施例3的方法对10克4-氨基苯甲酸乙酯进行重氮化。破坏掉多余的亚硝酸。在0℃用少量乙酸钠和氢氧化钠水溶液使重氮盐溶液的PH值至4.5-6.5,然后将14.85克的实施例2提到的磺基吡啶酮以水溶液形式加入,而同时使偶合物料的PH维持在上述范围内。这样生成25克如下通式的染料。
按常法在PH6.5进行,分离和进行干燥。此染料在水中生成黄色溶液,并将革、聚己内酰胺织物和羊毛染成深柠檬黄至金黄色调。其染色具有良好的光牢度和湿牢度。
实施例5
在PH8-9和在高温下,用氢氧化钠的溶液使16.7克4-氨基苯-4-磺酸溶于100毫升水中。然后加入20毫升23%重量浓度的亚硝酸钠水溶液,并在搅拌下使物料冷却。用冰冷却至0℃后,用20毫升浓盐酸使之酸化。让所得的悬浮液在0-5℃搅拌4小时。然后将过量的亚硝酸破坏掉,用少量乙酸钠和氢氧化钠溶液使悬浮液的PH升至4.5-5.5,并用与实施例4相似的方式加入实施例1中所述的14.5克的偶合组分的钠盐水溶液。然后,用氢氧化钠水溶液将反应混合物调节到PH5.5。用氯化钠将所得的染料沉淀出,以常法将沉淀分离出并干燥,得到31克如下通式的红橙粉末:
此粉末在水中生成金黄色溶液。此染料将羊毛、聚己内酰胺织物和革染成牢度良好的深橙色。
实施例1至5的制法也给出下面表1和表2中所描述的染料。
Claims (9)
2、权利要求1中所要求的偶氮染料,其中,D是来自苯胺,来自氨基萘或来自五元芳族杂环胺的重氮组分基团,此杂环胺含有一至三个选自杂环中的由氮,氧和硫所组成的杂原子类,此杂环环带有或不带有稠合在其上的苯环、噻吩环、吡啶环或嘧啶环。
3、权利要求1中所要求的偶氮染料,式中D是来自苯胺、来自氨基萘或来自杂环胺的重氮组分基团,而此杂环胺是吡咯,呋喃,噻吩,吡唑,咪唑,¥唑,异¥唑,噻唑,异噻唑,三唑,¥二唑,噻二唑,苯并呋喃,苯并噻吩,苯并咪唑,苯并¥唑,苯并噻吩,苯并异噻吩,吡啶并噻吩,嘧啶并噻吩,噻吩并噻吩或噻吩并噻唑系列的。
4、权利要求1中要求的偶氮染料,其中D是来自苯胺或来自氨基萘的重氮组分基团。
5、权利要求1中要求的偶氮染料,其中D是来自苯胺的重氮组分基团。
6、权利要求1中要求的偶氮染料,其中D是来自氨基二苯甲酮,来自氨基偶氮苯或来自氨基苯甲酸的重氮组分基团。
7、权利要求1中要求的偶氮染料在染色或印染天然基质物或合成基质物方面的用途。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DEP4416266.9 | 1994-05-07 | ||
DE4416266A DE4416266A1 (de) | 1994-05-07 | 1994-05-07 | Verdoppelte saure Azofarbstoffe mit einer Kupplungskomponente aus der Hydroxypyridonreihe sowie deren Zwischenprodukte |
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CN1113506A true CN1113506A (zh) | 1995-12-20 |
Family
ID=6517633
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CN95106501A Pending CN1113506A (zh) | 1994-05-07 | 1995-05-05 | 含有羟基吡啶酮偶合组分的双酸性偶氮染料及其中间体 |
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US (2) | US5554737A (zh) |
EP (1) | EP0681004B1 (zh) |
JP (1) | JPH07304975A (zh) |
KR (1) | KR950032480A (zh) |
CN (1) | CN1113506A (zh) |
BR (1) | BR9501925A (zh) |
DE (2) | DE4416266A1 (zh) |
ES (1) | ES2103141T3 (zh) |
Cited By (1)
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CN1090205C (zh) * | 1997-03-19 | 2002-09-04 | 株式会社上野制药应用研究所 | 稠环偶氮化合物、其制法及其用途 |
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KR20010017486A (ko) * | 1999-08-12 | 2001-03-05 | 손동준 | 수용성 아조염료와 그의 응용 |
US6582502B2 (en) * | 2000-01-25 | 2003-06-24 | Fuji Photo Film Co., Ltd. | Dye, ink for ink jet recording, and ink jet recording method |
US6696552B2 (en) * | 2002-06-27 | 2004-02-24 | Xerox Corporation | Process for preparing substituted pyridone compounds |
US7666317B2 (en) | 2005-01-31 | 2010-02-23 | MAC Aerospace Industries, Inc. | Methods and systems for disinfecting potable water supplies |
DE112014004448T5 (de) * | 2013-09-27 | 2016-06-23 | Canon Kabushiki Kaisha | Farbstoffverbindung, Tinte und Resistzusammensetzung für einen Farbfilter |
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US1880646A (en) * | 1932-10-04 | Certificate of correction | ||
US2406972A (en) * | 1943-02-24 | 1946-09-03 | Pyridium Corp | Processes for production of pyridine 3-sulphonic acid and its salts |
US3674794A (en) * | 1970-03-18 | 1972-07-04 | Ciba Geigy Corp | Certain-3-pyridine-sulfonamide derivatives |
US3912744A (en) * | 1971-04-10 | 1975-10-14 | Cassella Farbwerke Mainkur Ag | Hydroxy-pyrid one-monosulfonic acids |
US3912745A (en) * | 1971-04-10 | 1975-10-14 | Cassella Farbwerke Mainkur Ag | Hydroxy-pyridone-monosulfonic acids |
US4083842A (en) * | 1971-08-20 | 1978-04-11 | Sandoz Ltd. | Diazo compounds containing two optionally substituted-5-arylazo-6-hydroxypyridone-2 radicals linked through their nitrogen atoms |
DE3434921A1 (de) * | 1984-09-22 | 1986-05-07 | Sandoz-Patent-GmbH, 7850 Lörrach | Heterocyclische monoazoverbindungen |
GB8530458D0 (en) * | 1985-12-11 | 1986-01-22 | Ciba Geigy Ag | Anti-halation dyes |
EP0313051B1 (en) * | 1987-10-20 | 1996-06-12 | Fuji Photo Film Co., Ltd. | Silver halide photographic material |
DE59104208D1 (de) * | 1990-06-19 | 1995-02-23 | Bayer Ag | Azoreaktivfarbstoffe. |
EP0572450B1 (de) * | 1991-02-20 | 1994-10-26 | BASF Aktiengesellschaft | Azofarbstoffe mit einer diazokomponente aus der aminobenzophenonreihe sowie disulfonierte pyridonverbindungen |
-
1994
- 1994-05-07 DE DE4416266A patent/DE4416266A1/de not_active Withdrawn
-
1995
- 1995-04-27 ES ES95106327T patent/ES2103141T3/es not_active Expired - Lifetime
- 1995-04-27 DE DE59500341T patent/DE59500341D1/de not_active Expired - Lifetime
- 1995-04-27 EP EP95106327A patent/EP0681004B1/de not_active Expired - Lifetime
- 1995-05-02 JP JP7108895A patent/JPH07304975A/ja not_active Withdrawn
- 1995-05-02 US US08/432,815 patent/US5554737A/en not_active Expired - Fee Related
- 1995-05-04 KR KR1019950010995A patent/KR950032480A/ko not_active Application Discontinuation
- 1995-05-05 BR BR9501925A patent/BR9501925A/pt not_active Application Discontinuation
- 1995-05-05 CN CN95106501A patent/CN1113506A/zh active Pending
- 1995-12-28 US US08/580,124 patent/US5621107A/en not_active Expired - Fee Related
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN1090205C (zh) * | 1997-03-19 | 2002-09-04 | 株式会社上野制药应用研究所 | 稠环偶氮化合物、其制法及其用途 |
Also Published As
Publication number | Publication date |
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EP0681004A1 (de) | 1995-11-08 |
ES2103141T3 (es) | 1997-08-16 |
US5621107A (en) | 1997-04-15 |
KR950032480A (ko) | 1995-12-20 |
BR9501925A (pt) | 1996-03-05 |
JPH07304975A (ja) | 1995-11-21 |
DE59500341D1 (de) | 1997-08-07 |
US5554737A (en) | 1996-09-10 |
EP0681004B1 (de) | 1997-07-02 |
DE4416266A1 (de) | 1995-11-09 |
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