CA1087172A - Dyestuffs, their preparation and use - Google Patents
Dyestuffs, their preparation and useInfo
- Publication number
- CA1087172A CA1087172A CA275,472A CA275472A CA1087172A CA 1087172 A CA1087172 A CA 1087172A CA 275472 A CA275472 A CA 275472A CA 1087172 A CA1087172 A CA 1087172A
- Authority
- CA
- Canada
- Prior art keywords
- amino
- radical
- dyestuff
- acid
- sulphonic acid
- 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
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 239000000975 dye Substances 0.000 claims abstract description 163
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000004043 dyeing Methods 0.000 claims abstract description 9
- 239000000463 material Substances 0.000 claims abstract description 7
- 239000001913 cellulose Substances 0.000 claims abstract description 5
- 229920002678 cellulose Polymers 0.000 claims abstract description 5
- 239000004952 Polyamide Substances 0.000 claims abstract description 4
- 150000001450 anions Chemical class 0.000 claims abstract description 4
- 229920002647 polyamide Polymers 0.000 claims abstract description 4
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 claims abstract description 4
- -1 alkylene radical Chemical class 0.000 claims description 86
- 150000003254 radicals Chemical class 0.000 claims description 73
- 230000008878 coupling Effects 0.000 claims description 59
- 238000010168 coupling process Methods 0.000 claims description 59
- 238000005859 coupling reaction Methods 0.000 claims description 59
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 50
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 32
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 30
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 239000000460 chlorine Substances 0.000 claims description 27
- 150000001412 amines Chemical class 0.000 claims description 24
- 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 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 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 claims description 11
- 150000004056 anthraquinones Chemical class 0.000 claims description 11
- 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 claims description 11
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 claims description 5
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims description 4
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 150000002790 naphthalenes Chemical class 0.000 claims description 4
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 3
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 3
- 150000004696 coordination complex Chemical class 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 125000004999 nitroaryl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 3
- 229910052720 vanadium Inorganic materials 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 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 claims description 2
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- WLFXSECCHULRRO-UHFFFAOYSA-N pyridine-2,6-diol Chemical compound OC1=CC=CC(O)=N1 WLFXSECCHULRRO-UHFFFAOYSA-N 0.000 claims description 2
- 229910006069 SO3H Inorganic materials 0.000 claims 6
- 239000000758 substrate Substances 0.000 claims 3
- XRIGHGYEGNDPEU-UHFFFAOYSA-N 1-anilinoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NC1=CC=CC=C1 XRIGHGYEGNDPEU-UHFFFAOYSA-N 0.000 claims 2
- 125000003363 1,3,5-triazinyl group Chemical class N1=C(N=CN=C1)* 0.000 claims 1
- NGUUMHKSNSFLOS-UHFFFAOYSA-N 2-methoxyethyl hydrogen carbonate Chemical compound COCCOC(O)=O NGUUMHKSNSFLOS-UHFFFAOYSA-N 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 2
- 229930195733 hydrocarbon Natural products 0.000 abstract description 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 2
- 239000004753 textile Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 166
- 239000000243 solution Substances 0.000 description 87
- 239000000306 component Substances 0.000 description 83
- 235000013350 formula milk Nutrition 0.000 description 83
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 65
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 63
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 52
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 50
- 239000000203 mixture Substances 0.000 description 36
- 150000004699 copper complex Chemical class 0.000 description 34
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 34
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- 235000017550 sodium carbonate Nutrition 0.000 description 26
- 229910000029 sodium carbonate Inorganic materials 0.000 description 26
- 229940001593 sodium carbonate Drugs 0.000 description 26
- 235000002639 sodium chloride Nutrition 0.000 description 26
- 239000011780 sodium chloride Substances 0.000 description 25
- 229960002668 sodium chloride Drugs 0.000 description 25
- 239000000725 suspension Substances 0.000 description 25
- 230000007935 neutral effect Effects 0.000 description 23
- 235000011121 sodium hydroxide Nutrition 0.000 description 21
- 229940083608 sodium hydroxide Drugs 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 238000004519 manufacturing process Methods 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- 125000002252 acyl group Chemical group 0.000 description 9
- 150000008049 diazo compounds Chemical class 0.000 description 9
- 235000011167 hydrochloric acid Nutrition 0.000 description 9
- 229960000443 hydrochloric acid Drugs 0.000 description 9
- JJYPMNFTHPTTDI-UHFFFAOYSA-N meta-toluidine Natural products CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 8
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 8
- 229910052804 chromium Inorganic materials 0.000 description 8
- 239000011651 chromium Substances 0.000 description 8
- JVMSQRAXNZPDHF-UHFFFAOYSA-N 2,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(N)=C1 JVMSQRAXNZPDHF-UHFFFAOYSA-N 0.000 description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 7
- 210000004940 nucleus Anatomy 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 6
- REJHVSOVQBJEBF-UHFFFAOYSA-N 5-azaniumyl-2-[2-(4-azaniumyl-2-sulfonatophenyl)ethenyl]benzenesulfonate Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1C=CC1=CC=C(N)C=C1S(O)(=O)=O REJHVSOVQBJEBF-UHFFFAOYSA-N 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 6
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000005185 salting out Methods 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 238000001694 spray drying Methods 0.000 description 6
- LDCCBULMAFILCT-UHFFFAOYSA-N 2-aminobenzene-1,4-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1S(O)(=O)=O LDCCBULMAFILCT-UHFFFAOYSA-N 0.000 description 5
- DTNODBHGOLWROS-UHFFFAOYSA-N 3-amino-4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1N DTNODBHGOLWROS-UHFFFAOYSA-N 0.000 description 5
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 5
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- ZNXSFVXZQBETRJ-UHFFFAOYSA-N (3-aminophenyl)urea Chemical compound NC(=O)NC1=CC=CC(N)=C1 ZNXSFVXZQBETRJ-UHFFFAOYSA-N 0.000 description 4
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 4
- HEAHMJLHQCESBZ-UHFFFAOYSA-N 2,5-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(N)C(S(O)(=O)=O)=C1 HEAHMJLHQCESBZ-UHFFFAOYSA-N 0.000 description 4
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 4
- LTPSRQRIPCVMKQ-UHFFFAOYSA-N 2-amino-5-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C(S(O)(=O)=O)=C1 LTPSRQRIPCVMKQ-UHFFFAOYSA-N 0.000 description 4
- LTASFWDWBYFZQQ-UHFFFAOYSA-N 2-amino-5-nitrobenzenesulfonic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O LTASFWDWBYFZQQ-UHFFFAOYSA-N 0.000 description 4
- FLIOATBXVNLPLK-UHFFFAOYSA-N 3-amino-4-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(S(O)(=O)=O)C=C1N FLIOATBXVNLPLK-UHFFFAOYSA-N 0.000 description 4
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 4
- FOINSAWEWXUXPQ-UHFFFAOYSA-N 4-acetamido-2-aminobenzenesulfonic acid Chemical compound CC(=O)NC1=CC=C(S(O)(=O)=O)C(N)=C1 FOINSAWEWXUXPQ-UHFFFAOYSA-N 0.000 description 4
- ZDIRCGKEOWZBIM-UHFFFAOYSA-N 4-amino-2-methylbenzenesulfonic acid Chemical compound CC1=CC(N)=CC=C1S(O)(=O)=O ZDIRCGKEOWZBIM-UHFFFAOYSA-N 0.000 description 4
- KKBQCLVIBFUKGQ-UHFFFAOYSA-N 4-amino-5-methylbenzene-1,3-disulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=CC(S(O)(=O)=O)=C1N KKBQCLVIBFUKGQ-UHFFFAOYSA-N 0.000 description 4
- BRKFTWHPLMMNHF-UHFFFAOYSA-N 5-amino-2-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C=C1S(O)(=O)=O BRKFTWHPLMMNHF-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 4
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 4
- PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 description 4
- 239000001103 potassium chloride Substances 0.000 description 4
- 235000011164 potassium chloride Nutrition 0.000 description 4
- 229960002816 potassium chloride Drugs 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 3
- VOPSFYWMOIKYEM-UHFFFAOYSA-N 2,5-diaminobenzene-1,4-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=C(N)C=C1S(O)(=O)=O VOPSFYWMOIKYEM-UHFFFAOYSA-N 0.000 description 3
- CFCXQQUQLZIZPI-UHFFFAOYSA-N 2-amino-3,5-dimethylbenzenesulfonic acid Chemical compound CC1=CC(C)=C(N)C(S(O)(=O)=O)=C1 CFCXQQUQLZIZPI-UHFFFAOYSA-N 0.000 description 3
- VJHJWHAIOWSVCP-UHFFFAOYSA-N 2-amino-5-chloro-3-methylbenzenesulfonic acid Chemical compound CC1=CC(Cl)=CC(S(O)(=O)=O)=C1N VJHJWHAIOWSVCP-UHFFFAOYSA-N 0.000 description 3
- ZCGVPUAAMCMLTM-UHFFFAOYSA-N 2-amino-5-chlorobenzenesulfonic acid Chemical compound NC1=CC=C(Cl)C=C1S(O)(=O)=O ZCGVPUAAMCMLTM-UHFFFAOYSA-N 0.000 description 3
- ACHUDPKPXIEHAD-UHFFFAOYSA-N 2-amino-6-chlorobenzenesulfonic acid Chemical compound NC1=CC=CC(Cl)=C1S(O)(=O)=O ACHUDPKPXIEHAD-UHFFFAOYSA-N 0.000 description 3
- AFUHLZJMSIKUOK-UHFFFAOYSA-N 3,5-diamino-2-methylbenzenesulfonic acid Chemical compound CC1=C(N)C=C(N)C=C1S(O)(=O)=O AFUHLZJMSIKUOK-UHFFFAOYSA-N 0.000 description 3
- XIWOCDXCEHPARQ-UHFFFAOYSA-N 3-amino-2-methyl-5-nitrobenzenesulfonic acid Chemical compound CC1=C(N)C=C([N+]([O-])=O)C=C1S(O)(=O)=O XIWOCDXCEHPARQ-UHFFFAOYSA-N 0.000 description 3
- XJQRCFRVWZHIPN-UHFFFAOYSA-N 3-amino-4-chlorobenzenesulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1Cl XJQRCFRVWZHIPN-UHFFFAOYSA-N 0.000 description 3
- GADKYCGOSLZAKG-UHFFFAOYSA-N 3-amino-4-ethoxybenzenesulfonic acid Chemical compound CCOC1=CC=C(S(O)(=O)=O)C=C1N GADKYCGOSLZAKG-UHFFFAOYSA-N 0.000 description 3
- MUQWDMCEFASSPA-UHFFFAOYSA-N 3-amino-4-methylbenzene-1,2-disulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C(S(O)(=O)=O)=C1N MUQWDMCEFASSPA-UHFFFAOYSA-N 0.000 description 3
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- NEECEUZBAHTVIN-UHFFFAOYSA-N 4-amino-3-chlorobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1Cl NEECEUZBAHTVIN-UHFFFAOYSA-N 0.000 description 3
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- URZPSKKSHSLKIR-UHFFFAOYSA-N 5-methyl-2-(5-methyl-3-oxo-1h-pyrazol-2-yl)benzenesulfonic acid Chemical compound N1C(C)=CC(=O)N1C1=CC=C(C)C=C1S(O)(=O)=O URZPSKKSHSLKIR-UHFFFAOYSA-N 0.000 description 1
- GQOCHGGAHCGHGI-UHFFFAOYSA-N 6-amino-5-hydroxy-8-nitronaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=C(O)C(N)=CC([N+]([O-])=O)=C21 GQOCHGGAHCGHGI-UHFFFAOYSA-N 0.000 description 1
- KZCSUEYBKAPKNH-UHFFFAOYSA-N 6-aminonaphthalene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KZCSUEYBKAPKNH-UHFFFAOYSA-N 0.000 description 1
- PJQUFZPSUQYROE-UHFFFAOYSA-N 7-[(2-acetamido-4-aminophenyl)diazenyl]naphthalene-1,3,6-trisulfonic acid Chemical compound CC(=O)NC1=CC(N)=CC=C1N=NC1=CC2=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C=C2C=C1S(O)(=O)=O PJQUFZPSUQYROE-UHFFFAOYSA-N 0.000 description 1
- DWGBLODXAMYUOP-UHFFFAOYSA-N 7-amino-3-nitronaphthalene-1-sulfonic acid Chemical compound C1=C([N+]([O-])=O)C=C(S(O)(=O)=O)C2=CC(N)=CC=C21 DWGBLODXAMYUOP-UHFFFAOYSA-N 0.000 description 1
- HXCAOTTUHMNTPB-UHFFFAOYSA-N 7-amino-4-hydroxy-3-[(2-hydroxy-5-nitro-3-sulfophenyl)diazenyl]naphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC2=CC(N)=CC=C2C(O)=C1N=NC1=CC([N+]([O-])=O)=CC(S(O)(=O)=O)=C1O HXCAOTTUHMNTPB-UHFFFAOYSA-N 0.000 description 1
- HKTWHHAJDJCUPC-UHFFFAOYSA-N 7-aminonaphthalene-1,3,5-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 HKTWHHAJDJCUPC-UHFFFAOYSA-N 0.000 description 1
- FYVOTMMSGKWFPK-UHFFFAOYSA-N 7-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC=C21 FYVOTMMSGKWFPK-UHFFFAOYSA-N 0.000 description 1
- HMNPDEGBVWDHAR-UHFFFAOYSA-N 8-aminonaphthalen-1-ol Chemical compound C1=CC(O)=C2C(N)=CC=CC2=C1 HMNPDEGBVWDHAR-UHFFFAOYSA-N 0.000 description 1
- UBDHSURDYAETAL-UHFFFAOYSA-N 8-aminonaphthalene-1,3,6-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 UBDHSURDYAETAL-UHFFFAOYSA-N 0.000 description 1
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 1
- DQIVFTJHYKDOMZ-UHFFFAOYSA-N 96-67-3 Chemical compound NC1=CC([N+]([O-])=O)=CC(S(O)(=O)=O)=C1O DQIVFTJHYKDOMZ-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000905957 Channa melasoma Species 0.000 description 1
- ZIEZSHKUKVICHE-UHFFFAOYSA-N ClC=1C(=NN=NC1S(=O)(=O)O)S(=O)(=O)O Chemical compound ClC=1C(=NN=NC1S(=O)(=O)O)S(=O)(=O)O ZIEZSHKUKVICHE-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 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
- LRPPWXBTUMEWJM-UHFFFAOYSA-N OC1=CC(=CC2=CC(NC(=S)NC3=CC=C4C(O)=CC(=CC4=C3)S(O)(=O)=O)=CC=C12)S(O)(=O)=O Chemical compound OC1=CC(=CC2=CC(NC(=S)NC3=CC=C4C(O)=CC(=CC4=C3)S(O)(=O)=O)=CC=C12)S(O)(=O)=O LRPPWXBTUMEWJM-UHFFFAOYSA-N 0.000 description 1
- OVVCEJNUYJRFAM-UHFFFAOYSA-N S(=O)(=O)(O)C1=C(C=CC(=C1)NC=1N(NN=CC1Cl)Cl)N1NC(=C(C1=O)N=NC1=C(C=CC=C1)S(=O)(=O)O)C(=O)O Chemical compound S(=O)(=O)(O)C1=C(C=CC(=C1)NC=1N(NN=CC1Cl)Cl)N1NC(=C(C1=O)N=NC1=C(C=CC=C1)S(=O)(=O)O)C(=O)O OVVCEJNUYJRFAM-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- UJDPOQPBERLOOI-UHFFFAOYSA-N aniline;n-methylaniline Chemical compound NC1=CC=CC=C1.CNC1=CC=CC=C1 UJDPOQPBERLOOI-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000004700 cobalt complex Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000003546 flue gas Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 235000013905 glycine and its sodium salt Nutrition 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
- 150000007857 hydrazones Chemical class 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical group CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000004045 reactive dyeing Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- 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
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
- D06P1/382—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes reactive group directly attached to heterocyclic group
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2614550.6 | 1976-04-03 | ||
| DE2614550A DE2614550C3 (de) | 1976-04-03 | 1976-04-03 | Neue Reaktivfarbstoffe, ihre Herstellung und Verwendung zum Färben und Bedrucken von Cellulose sowie natürlichen und synthetischen Polyamidsubstraten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1087172A true CA1087172A (en) | 1980-10-07 |
Family
ID=5974425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA275,472A Expired CA1087172A (en) | 1976-04-03 | 1977-04-04 | Dyestuffs, their preparation and use |
Country Status (12)
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5792054A (en) * | 1980-11-28 | 1982-06-08 | Nippon Kayaku Co Ltd | Copper-containing reactive dye |
| DE3272886D1 (en) * | 1981-07-21 | 1986-10-02 | Ciba Geigy Ag | Reactive dyestuffs, their preparation and their use |
| EP0074928A3 (de) * | 1981-09-16 | 1983-04-20 | Ciba-Geigy Ag | Reaktivfarbstoffe, deren Herstellung und Verwendung |
| DE3269650D1 (en) * | 1981-10-02 | 1986-04-10 | Ciba Geigy Ag | Reactive dyestuffs, their preparation and their use |
| DE3145571A1 (de) * | 1981-11-17 | 1983-05-26 | Hoechst Ag, 6230 Frankfurt | "wasserloesliche 1:2-metallkomplex-azoverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe" |
| EP0131542B1 (de) * | 1983-06-10 | 1989-04-19 | Ciba-Geigy Ag | Reaktivfarbstoffe, deren Herstellung und Verwendung |
| DE3464626D1 (en) * | 1983-08-30 | 1987-08-13 | Ciba Geigy Ag | Reactive dyes, their preparation and their use |
| EP0141367B1 (de) * | 1983-10-26 | 1988-03-30 | Ciba-Geigy Ag | Reaktivfarbstoffe, deren Herstellung und Verwendung |
| CH660016A5 (de) * | 1983-11-09 | 1987-03-13 | Ciba Geigy Ag | Reaktivfarbstoffe und deren herstellung. |
| JPS59161463A (ja) * | 1984-02-13 | 1984-09-12 | Sumitomo Chem Co Ltd | モノアゾ化合物およびその製造方法 |
| JPH07116375B2 (ja) * | 1984-02-20 | 1995-12-13 | 住友化学工業株式会社 | トリアジン化合物およびそれを用いる繊維材料の染色または捺染法 |
| DE3561325D1 (en) * | 1984-04-05 | 1988-02-11 | Ciba Geigy Ag | Reactive dyes, their preparation and their use |
| EP0179019B1 (de) * | 1984-10-15 | 1990-05-16 | Ciba-Geigy Ag | Reaktivfarbstoffe, deren Herstellung und Verwendung |
| EP0208655B1 (de) * | 1985-07-12 | 1990-08-16 | Ciba-Geigy Ag | Reaktivfarbstoffe, deren Herstellung und Verwendung |
| US5023325A (en) * | 1985-07-12 | 1991-06-11 | Ciba-Geigy Corporation | Fibre-reactive dyes containing a substituted aminocarbonyl-phenylamino or naphthylamino reactive moiety |
| EP0214093B1 (de) | 1985-08-14 | 1990-01-03 | Ciba-Geigy Ag | Reaktivfarbstoffe, deren Herstellung und Verwendung |
| US4766206A (en) * | 1985-10-03 | 1988-08-23 | Ciba-Geigy Corporation | Reactive dyestuffs comprising a vinylsulfonylalkylaminocarbonyl moiety |
| DE3868300D1 (de) * | 1987-07-03 | 1992-03-19 | Ciba Geigy Ag | Reaktivfarbstoffe, verfahren zu deren herstellung und deren verwendung. |
| DE3731202A1 (de) * | 1987-09-17 | 1989-07-13 | Basf Ag | Doppelankerreaktivfarbstoffe und benzylsulfonylverbindungen als deren zwischenprodukte |
| DE3872337D1 (de) * | 1987-09-24 | 1992-07-30 | Ciba Geigy Ag | Reaktivfarbstoffe, deren herstellung und verwendung. |
| US4925928A (en) * | 1988-06-23 | 1990-05-15 | Ciba-Geigy Corporation | Reactive dyes containing vinylsulfonylalkylamino bound to a bis-(triazinylamino)-benzene group |
| DE3843014A1 (de) * | 1988-12-21 | 1990-06-28 | Hoechst Ag | Wasserloesliche farbstoffe, verfahren zu ihrer herstellung und ihre verwendung |
| US5243034A (en) * | 1988-12-21 | 1993-09-07 | Hoechst Aktiengesellschaft | Disazo dyestuffs having a triazine moiety and a fiberreactive group of vinylsulfone series |
| DE3917369A1 (de) * | 1989-05-29 | 1990-12-06 | Hoechst Ag | Wasserloesliche faserreaktive farbstoffe, verfahren zu ihrer herstellung und ihre verwendung |
| DE4214740A1 (de) * | 1992-05-04 | 1993-11-11 | Bayer Ag | Reaktivfarbstoffe, deren Herstellung und Verwendung |
| DE59303537D1 (de) * | 1992-05-04 | 1996-10-02 | Bayer Ag | Reaktivfarbstoffe, deren Herstellung und Verwendung |
| EP0624630A1 (de) * | 1993-05-13 | 1994-11-17 | Hoechst Aktiengesellschaft | Wasserlösliche faserreaktive Farbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE59405289D1 (de) * | 1993-05-18 | 1998-04-02 | Hoechst Ag | Wasserlöslichse faserreaktive Farbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE4318620A1 (de) * | 1993-06-04 | 1994-12-08 | Bayer Ag | Reaktivfarbstoffe |
| DE4320447A1 (de) * | 1993-06-21 | 1994-12-22 | Hoechst Ag | Wasserlösliche faserreaktive Azofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE4338117A1 (de) | 1993-11-08 | 1995-05-11 | Bayer Ag | Reaktivfarbstoffe, deren Herstellung und Verwendung |
| DE4415692A1 (de) * | 1994-05-04 | 1995-11-09 | Hoechst Ag | Wasserlösliche Triphendioxazinverbindungen, Verfahren zu deren Herstellung und ihre Verwendung als Farbstoffe |
| EP0775730B1 (de) * | 1995-11-23 | 2000-05-03 | Ciba SC Holding AG | Reaktivfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung |
| EP0775731B1 (de) * | 1995-11-23 | 1999-12-29 | Ciba SC Holding AG | Reaktivfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung |
| DE59611474D1 (de) * | 1995-11-23 | 2008-07-03 | Huntsman Adv Mat Switzerland | Faserreaktive Anthrachinonfarbstoffe, deren Herstellung und deren Verwendung |
| JPH09324130A (ja) * | 1996-06-05 | 1997-12-16 | Sumitomo Chem Co Ltd | モノアゾ化合物及びそれを用いる繊維材料の染色又は捺染方法 |
| US5998591A (en) * | 1997-05-22 | 1999-12-07 | Sumitomo Chemical Company, Limited | Fiber-reactive bisazo compound |
| CN1419589A (zh) | 2000-03-22 | 2003-05-21 | 西巴特殊化学品控股有限公司 | 纤维活性萘基偶氮基萘基三嗪基染料 |
| WO2013182349A1 (en) * | 2012-06-05 | 2013-12-12 | Huntsman Advanced Materials (Switzerland) Gmbh | Reactive dyes, their preparation and their use |
| JP6118833B2 (ja) * | 2014-03-27 | 2017-04-19 | 富士フイルム株式会社 | 化合物、着色組成物、インクジェット記録用インク、インクジェット記録方法、インクジェットプリンタカートリッジ、及びインクジェット記録物 |
| US20230090216A1 (en) * | 2020-01-29 | 2023-03-23 | Huntsman Advanced Materials Switzerland Gmbh | Functionalized particles |
| KR102787946B1 (ko) * | 2020-04-27 | 2025-03-31 | 아크로마 (스위처랜드) 게엠베하 | 반응성 염료들의 혼합물 및 텍스타일 섬유 재료를 염색 또는 프린팅하기 위한 이의 용도 |
| TW202340390A (zh) | 2022-01-25 | 2023-10-16 | 瑞士商亨斯邁紡織染化（瑞士）有限公司 | 反應性染料的異構混合物及其在紡織纖維材料的染色或印花的用途 |
| CN116814090B (zh) * | 2023-06-11 | 2024-10-18 | 水木聚力接枝纺织新技术(深圳)有限公司 | 一种水溶性双丙烯酰基氨基c酸染料及其合成方法和用途 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH407373A (de) * | 1960-10-28 | 1966-02-15 | Ciba Geigy | Verfahren zur Herstellung neuer Farbstoffe |
| GB987074A (en) * | 1961-03-24 | 1965-03-24 | Ciba Ltd | New reactive metallised monoazo-dyestuffs and their manufacture and use |
| DE1265698C2 (de) * | 1961-05-06 | 1968-11-07 | Hoechst Ag | Verfahren zur Erzeugung von nassechten Faerbungen und Drucken |
| DE1793172C3 (de) * | 1968-08-10 | 1974-05-16 | Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt | Anthrachinonfarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
| CH514659A (de) * | 1968-08-12 | 1971-10-31 | Cassella Farbwerke Mainkur Ag | Verfahren zur Herstellung wasserlöslicher metallhaltiger Farbstoffe der Phthalocyaninreihe |
-
1976
- 1976-04-03 DE DE2614550A patent/DE2614550C3/de not_active Expired
-
1977
- 1977-03-25 NL NL7703274A patent/NL7703274A/xx not_active Application Discontinuation
- 1977-03-26 IN IN457/CAL/1977A patent/IN145278B/en unknown
- 1977-03-29 IT IT21830/77A patent/IT1075683B/it active
- 1977-03-31 JP JP52035513A patent/JPS603109B2/ja not_active Expired
- 1977-04-01 CH CH414677A patent/CH622818A5/de not_active IP Right Cessation
- 1977-04-01 ES ES457444A patent/ES457444A1/es not_active Expired
- 1977-04-01 BE BE176372A patent/BE853181A/xx not_active IP Right Cessation
- 1977-04-01 GB GB13852/77A patent/GB1576237A/en not_active Expired
- 1977-04-01 BR BR7702070A patent/BR7702070A/pt unknown
- 1977-04-04 CA CA275,472A patent/CA1087172A/en not_active Expired
- 1977-04-04 FR FR7710075A patent/FR2346418A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IN145278B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-09-23 |
| JPS603109B2 (ja) | 1985-01-25 |
| GB1576237A (en) | 1980-10-01 |
| BR7702070A (pt) | 1977-11-08 |
| IT1075683B (it) | 1985-04-22 |
| DE2614550C3 (de) | 1981-06-25 |
| DE2614550A1 (de) | 1977-10-27 |
| JPS52121039A (en) | 1977-10-12 |
| FR2346418B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-05-09 |
| CH622818A5 (en) | 1981-04-30 |
| FR2346418A1 (fr) | 1977-10-28 |
| BE853181A (fr) | 1977-10-03 |
| DE2614550B2 (de) | 1980-07-10 |
| ES457444A1 (es) | 1978-03-01 |
| NL7703274A (nl) | 1977-10-05 |
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