CN1097075C - 活性染料及其制备与应用 - Google Patents
活性染料及其制备与应用 Download PDFInfo
- Publication number
- CN1097075C CN1097075C CN96112340A CN96112340A CN1097075C CN 1097075 C CN1097075 C CN 1097075C CN 96112340 A CN96112340 A CN 96112340A CN 96112340 A CN96112340 A CN 96112340A CN 1097075 C CN1097075 C CN 1097075C
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- China
- Prior art keywords
- group
- sulfo group
- formula
- disulfo
- phenylene
- 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.)
- Expired - Fee Related
Links
- 238000002360 preparation method Methods 0.000 title claims description 37
- 239000000985 reactive dye Substances 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- -1 sulfato Chemical group 0.000 claims description 288
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 67
- 239000000975 dye Substances 0.000 claims description 65
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 63
- 239000000460 chlorine Substances 0.000 claims description 58
- 229910052757 nitrogen Inorganic materials 0.000 claims description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 150000002367 halogens Chemical class 0.000 claims description 28
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 17
- 239000000463 material Substances 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 11
- 229920002554 vinyl polymer Polymers 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 239000000835 fiber Substances 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
- ODFJOVXVLFUVNQ-UHFFFAOYSA-N acetarsol Chemical compound CC(=O)NC1=CC([As](O)(O)=O)=CC=C1O ODFJOVXVLFUVNQ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052727 yttrium Inorganic materials 0.000 claims description 8
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
- 239000010452 phosphate Substances 0.000 claims description 5
- 229920003043 Cellulose fiber Polymers 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 239000005864 Sulphur Substances 0.000 claims description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 2
- 125000002905 alkanoylamido group Chemical group 0.000 claims description 2
- 125000005466 alkylenyl group Chemical group 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
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 claims 1
- 238000004043 dyeing Methods 0.000 abstract description 16
- 239000002657 fibrous material Substances 0.000 abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 156
- 239000000243 solution Substances 0.000 description 140
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 59
- 238000006243 chemical reaction Methods 0.000 description 49
- 239000002253 acid Substances 0.000 description 41
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 33
- 238000006482 condensation reaction Methods 0.000 description 28
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 24
- 230000007935 neutral effect Effects 0.000 description 23
- 239000000203 mixture Substances 0.000 description 22
- 239000002585 base Substances 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 239000004744 fabric Substances 0.000 description 17
- 235000010288 sodium nitrite Nutrition 0.000 description 17
- 229920000742 Cotton Polymers 0.000 description 16
- 238000010168 coupling process Methods 0.000 description 16
- 238000006193 diazotization reaction Methods 0.000 description 15
- 150000002790 naphthalenes Chemical class 0.000 description 15
- 239000000047 product Substances 0.000 description 13
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
- 238000000502 dialysis Methods 0.000 description 12
- 150000002826 nitrites Chemical class 0.000 description 12
- QPILZZVXGUNELN-UHFFFAOYSA-M sodium;4-amino-5-hydroxynaphthalene-2,7-disulfonate;hydron Chemical group [Na+].OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S([O-])(=O)=O)=CC2=C1 QPILZZVXGUNELN-UHFFFAOYSA-M 0.000 description 12
- 150000001805 chlorine compounds Chemical class 0.000 description 11
- 229920002678 cellulose Polymers 0.000 description 10
- 239000001913 cellulose Substances 0.000 description 10
- IALORYHODRVWKZ-UHFFFAOYSA-N 2-(4-aminophenyl)sulfonylethyl sulfate;hydron Chemical compound NC1=CC=C(S(=O)(=O)CCOS(O)(=O)=O)C=C1 IALORYHODRVWKZ-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 229910017053 inorganic salt Inorganic materials 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 8
- 239000000344 soap Substances 0.000 description 8
- 239000000872 buffer Substances 0.000 description 7
- 230000008878 coupling Effects 0.000 description 7
- 238000005859 coupling reaction Methods 0.000 description 7
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 7
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 7
- 239000002953 phosphate buffered saline Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000003599 detergent Substances 0.000 description 6
- 210000002268 wool Anatomy 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 150000002222 fluorine compounds Chemical class 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical class C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
- 238000009980 pad dyeing Methods 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 238000001354 calcination Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 3
- PPSSQRUPSRPZON-UHFFFAOYSA-N nitrobenzene;sodium Chemical compound [Na].[O-][N+](=O)C1=CC=CC=C1 PPSSQRUPSRPZON-UHFFFAOYSA-N 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 2
- BDCJBCKISOZMBR-UHFFFAOYSA-N 2-amino-4-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(S(O)(=O)=O)C(N)=C1 BDCJBCKISOZMBR-UHFFFAOYSA-N 0.000 description 2
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical group C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 2
- ZCNCWYFISJTFHB-UHFFFAOYSA-N 4-hydroxy-7-(methylamino)naphthalene-2-sulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(NC)=CC=C21 ZCNCWYFISJTFHB-UHFFFAOYSA-N 0.000 description 2
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 241000872198 Serjania polyphylla Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229910052770 Uranium Inorganic materials 0.000 description 2
- 229940072056 alginate Drugs 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 2
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 2
- 235000011167 hydrochloric acid Nutrition 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 description 1
- NVVVYBVTAFSWNQ-UHFFFAOYSA-N (propanoylamino)urea Chemical group CCC(=O)NNC(N)=O NVVVYBVTAFSWNQ-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- KZKGEEGADAWJFS-UHFFFAOYSA-N 2-amino-5-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(N)C(S(O)(=O)=O)=C1 KZKGEEGADAWJFS-UHFFFAOYSA-N 0.000 description 1
- YAIKCRUPEVOINQ-UHFFFAOYSA-N 2-aminonaphthalene-1,5-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 YAIKCRUPEVOINQ-UHFFFAOYSA-N 0.000 description 1
- QEFPDISKVNULGA-UHFFFAOYSA-N 2-aminonaphthalene-1,6-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=C(S(O)(=O)=O)C(N)=CC=C21 QEFPDISKVNULGA-UHFFFAOYSA-N 0.000 description 1
- KQZBSZUGKSCFBL-UHFFFAOYSA-N 2-phenyldiazenylaniline Chemical compound NC1=CC=CC=C1N=NC1=CC=CC=C1 KQZBSZUGKSCFBL-UHFFFAOYSA-N 0.000 description 1
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- CMOLPZZVECHXKN-UHFFFAOYSA-N 7-aminonaphthalene-1,3-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC=C21 CMOLPZZVECHXKN-UHFFFAOYSA-N 0.000 description 1
- HUYJTJXLNBOVFO-UHFFFAOYSA-N 7-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(O)=CC=C21 HUYJTJXLNBOVFO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- IRSYXWPNUXHWBQ-UHFFFAOYSA-N C1(=CC=CC=C1)N=NC1=C(C2=CC=CC=C2C=C1)Cl Chemical compound C1(=CC=CC=C1)N=NC1=C(C2=CC=CC=C2C=C1)Cl IRSYXWPNUXHWBQ-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920004935 Trevira® Polymers 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical group 0.000 description 1
- BEHLMOQXOSLGHN-UHFFFAOYSA-N benzenamine sulfate Chemical compound OS(=O)(=O)NC1=CC=CC=C1 BEHLMOQXOSLGHN-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- WDEQGLDWZMIMJM-UHFFFAOYSA-N benzyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical compound OCC1CC(O)CN1C(=O)OCC1=CC=CC=C1 WDEQGLDWZMIMJM-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/4401—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system
- C09B62/4403—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system the heterocyclic system being a triazine ring
- C09B62/4411—Azo dyes
-
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/4401—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system
- C09B62/4403—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system the heterocyclic system being a triazine ring
- C09B62/4405—Dioxazine dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/66—Natural or regenerated cellulose using reactive dyes
- D06P3/666—Natural or regenerated cellulose using reactive dyes reactive group not directly attached to heterocyclic group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2675/95 | 1995-09-21 | ||
| CH267595 | 1995-09-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1157839A CN1157839A (zh) | 1997-08-27 |
| CN1097075C true CN1097075C (zh) | 2002-12-25 |
Family
ID=4239061
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN96112340A Expired - Fee Related CN1097075C (zh) | 1995-09-21 | 1996-09-20 | 活性染料及其制备与应用 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US5969113A (enExample) |
| EP (1) | EP0764694B1 (enExample) |
| JP (1) | JPH09111141A (enExample) |
| KR (1) | KR100460561B1 (enExample) |
| CN (1) | CN1097075C (enExample) |
| DE (1) | DE59608127D1 (enExample) |
| ES (1) | ES2164858T3 (enExample) |
| MY (1) | MY114028A (enExample) |
| PT (1) | PT764694E (enExample) |
| SG (1) | SG49978A1 (enExample) |
| TW (1) | TW440596B (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI260334B (en) * | 1999-11-01 | 2006-08-21 | Clariant Int Ltd | Azo dyestuffs |
| GB0012551D0 (en) * | 2000-05-23 | 2000-07-12 | Basf Ag | Reactive azo dyes |
| JP4822390B2 (ja) * | 2004-03-15 | 2011-11-24 | 日本化薬株式会社 | 水性黒色インク組成物及び着色体 |
| CN103030999A (zh) * | 2010-08-30 | 2013-04-10 | 天津德凯化工股份有限公司 | 一种尼龙活性红染料及其制备方法 |
| CN105504871A (zh) * | 2015-12-21 | 2016-04-20 | 湖北华丽染料工业有限公司 | 一种鲜艳红色活性染料及其制备方法与应用 |
| CN105504872A (zh) * | 2015-12-23 | 2016-04-20 | 湖北华丽染料工业有限公司 | 一种亮橙色活性染料及其制备方法和应用 |
| CN106833014B (zh) * | 2017-01-16 | 2018-08-03 | 东华大学 | 一种具有红黄蓝母体结构多发色体系的活性染料及其制备方法和应用 |
| CN107722667B (zh) * | 2017-11-16 | 2019-07-23 | 东华大学 | 一种基于蒽醌偶氮多发色基团的紫色活性染料及其制备方法和应用 |
| CN109535094B (zh) * | 2018-11-22 | 2021-09-21 | 东华大学 | 一种反应性弱碱可变色的偶氮-蒽醌类pH探针及其制备和应用 |
| CN110938039A (zh) * | 2019-11-15 | 2020-03-31 | 东华大学 | 一种基于三偶氮多发色体的紫色活性染料及其制备和应用 |
| CN110903678A (zh) * | 2019-11-15 | 2020-03-24 | 东华大学 | 一种基于j酸和h酸多发色体的活性染料及其制备和应用 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4806127A (en) * | 1986-08-30 | 1989-02-21 | Hoechst Aktiengesellschaft | Water-soluble disazo compounds, containing triazinyl pyridinium group processes for their preparation and their use for dyeing cellulose |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1366097A (en) * | 1971-09-10 | 1974-09-11 | Ici Ltd | Reactive metallised azo dyestuffs |
| GB1454210A (en) * | 1974-10-02 | 1976-11-03 | Ici Ltd | Reactive dyes |
| DE2748966C3 (de) * | 1977-11-02 | 1980-08-21 | Hoechst Ag, 6000 Frankfurt | Wasserlösliche Farbstoffe, Verfahren zu deren Herstellung, ihre Verwendung als faserreaktive Farbstoffe zum Färben und Bedrucken von Cellulose- und Polyamid-Fasermaterialien |
| EP0549530B1 (de) * | 1991-12-20 | 1995-12-13 | Ciba-Geigy Ag | Verfahren zum Färben oder Bedrucken von hydroxylgruppenhaltigen Fasermaterialien |
| JP2914869B2 (ja) * | 1993-05-06 | 1999-07-05 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | 繊維−反応性染料、それらの製造方法及び用途 |
| TW241289B (enExample) * | 1993-05-17 | 1995-02-21 | Ciba Geigy | |
| US5631352A (en) * | 1994-06-20 | 1997-05-20 | Ciba-Geigy Corporation | Azodyes containing a bridge member based on diamino-substituted triazines |
| DE59608185D1 (de) * | 1995-08-24 | 2001-12-20 | Ciba Sc Holding Ag | Reaktivfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung |
-
1996
- 1996-08-31 TW TW085110631A patent/TW440596B/zh not_active IP Right Cessation
- 1996-09-11 MY MYPI96003736A patent/MY114028A/en unknown
- 1996-09-12 DE DE59608127T patent/DE59608127D1/de not_active Expired - Fee Related
- 1996-09-12 EP EP96810607A patent/EP0764694B1/de not_active Expired - Lifetime
- 1996-09-12 PT PT96810607T patent/PT764694E/pt unknown
- 1996-09-12 ES ES96810607T patent/ES2164858T3/es not_active Expired - Lifetime
- 1996-09-19 SG SG9610739A patent/SG49978A1/en unknown
- 1996-09-20 CN CN96112340A patent/CN1097075C/zh not_active Expired - Fee Related
- 1996-09-20 JP JP8249619A patent/JPH09111141A/ja active Pending
- 1996-09-21 KR KR1019960042777A patent/KR100460561B1/ko not_active Expired - Fee Related
-
1997
- 1997-11-26 US US08/979,468 patent/US5969113A/en not_active Expired - Fee Related
-
2002
- 2002-08-16 US US10/222,309 patent/US6670457B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4806127A (en) * | 1986-08-30 | 1989-02-21 | Hoechst Aktiengesellschaft | Water-soluble disazo compounds, containing triazinyl pyridinium group processes for their preparation and their use for dyeing cellulose |
Also Published As
| Publication number | Publication date |
|---|---|
| MY114028A (en) | 2002-07-31 |
| PT764694E (pt) | 2002-04-29 |
| ES2164858T3 (es) | 2002-03-01 |
| US5969113A (en) | 1999-10-19 |
| TW440596B (en) | 2001-06-16 |
| KR970015677A (ko) | 1997-04-28 |
| US20030055230A1 (en) | 2003-03-20 |
| EP0764694B1 (de) | 2001-11-07 |
| SG49978A1 (en) | 2001-05-22 |
| DE59608127D1 (de) | 2001-12-13 |
| JPH09111141A (ja) | 1997-04-28 |
| KR100460561B1 (ko) | 2005-08-17 |
| CN1157839A (zh) | 1997-08-27 |
| HK1005553A1 (en) | 1999-01-15 |
| US6670457B2 (en) | 2003-12-30 |
| EP0764694A1 (de) | 1997-03-26 |
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