JPS58204051A - モノアゾ化合物及び該化合物を染料として使用する方法 - Google Patents
モノアゾ化合物及び該化合物を染料として使用する方法Info
- Publication number
- JPS58204051A JPS58204051A JP58081053A JP8105383A JPS58204051A JP S58204051 A JPS58204051 A JP S58204051A JP 58081053 A JP58081053 A JP 58081053A JP 8105383 A JP8105383 A JP 8105383A JP S58204051 A JPS58204051 A JP S58204051A
- Authority
- JP
- Japan
- Prior art keywords
- group
- atoms
- hydrogen atom
- formula
- atom
- 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.)
- Granted
Links
- -1 Monoazo compound Chemical class 0.000 title claims description 22
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 44
- 238000004043 dyeing Methods 0.000 claims description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 239000000463 material Substances 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 125000003277 amino group Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 10
- 150000002790 naphthalenes Chemical class 0.000 claims description 10
- 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 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 6
- 125000005521 carbonamide group Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical class C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 241000208140 Acer Species 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
- 239000010931 gold Substances 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 4
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims 4
- 241000220317 Rosa Species 0.000 claims 3
- 229910052751 metal Inorganic materials 0.000 claims 3
- 239000002184 metal Substances 0.000 claims 3
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical group C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims 1
- 201000009030 Carcinoma Diseases 0.000 claims 1
- 206010011224 Cough Diseases 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 150000004982 aromatic amines Chemical class 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 238000007447 staining method Methods 0.000 claims 1
- 239000000975 dye Substances 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
- 238000007639 printing Methods 0.000 description 11
- 239000000835 fiber Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 229920003043 Cellulose fiber Polymers 0.000 description 9
- 239000002657 fibrous material Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000000985 reactive dye Substances 0.000 description 7
- 239000004753 textile Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 239000004952 Polyamide Substances 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- 229920002678 cellulose Polymers 0.000 description 5
- 239000001913 cellulose Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229920002647 polyamide Polymers 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- 150000001989 diazonium salts Chemical class 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 210000002268 wool Anatomy 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 229940001593 sodium carbonate Drugs 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- HMNPDEGBVWDHAR-UHFFFAOYSA-N 8-aminonaphthalen-1-ol Chemical compound C1=CC(O)=C2C(N)=CC=CC2=C1 HMNPDEGBVWDHAR-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 2
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229910001424 calcium ion Inorganic materials 0.000 description 2
- 235000009120 camo Nutrition 0.000 description 2
- 235000005607 chanvre indien Nutrition 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 239000011487 hemp Substances 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 239000013535 sea water Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- VHYBUUMUUNCHCK-UHFFFAOYSA-N 2,4,6-tribromo-1,3,5-triazine Chemical compound BrC1=NC(Br)=NC(Br)=N1 VHYBUUMUUNCHCK-UHFFFAOYSA-N 0.000 description 1
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 240000008564 Boehmeria nivea Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229920000571 Nylon 11 Polymers 0.000 description 1
- 229920001007 Nylon 4 Polymers 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 244000124853 Perilla frutescens Species 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 241001085205 Prenanthella exigua Species 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- SAQSTQBVENFSKT-UHFFFAOYSA-M TCA-sodium Chemical compound [Na+].[O-]C(=O)C(Cl)(Cl)Cl SAQSTQBVENFSKT-UHFFFAOYSA-M 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000003287 bathing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- QXDMQSPYEZFLGF-UHFFFAOYSA-L calcium oxalate Chemical compound [Ca+2].[O-]C(=O)C([O-])=O QXDMQSPYEZFLGF-UHFFFAOYSA-L 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000013066 combination product Substances 0.000 description 1
- 229940127555 combination product Drugs 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000010014 continuous dyeing Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 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
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012526 feed medium Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 235000007686 potassium Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229940094025 potassium bicarbonate Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 150000003112 potassium compounds Chemical class 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229960004249 sodium acetate Drugs 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- ZNCPFRVNHGOPAG-UHFFFAOYSA-L sodium oxalate Chemical compound [Na+].[Na+].[O-]C(=O)C([O-])=O ZNCPFRVNHGOPAG-UHFFFAOYSA-L 0.000 description 1
- 229940039790 sodium oxalate Drugs 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000005406 washing Methods 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
- C09B29/28—Amino naphthols
- C09B29/30—Amino naphtholsulfonic acid
-
- 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
- C09B62/4413—Non-metallized monoazo 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
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
- C09B62/085—Monoazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Laminated Bodies (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823217812 DE3217812A1 (de) | 1982-05-12 | 1982-05-12 | Monoazoverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe |
| DE3217812.3 | 1982-05-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58204051A true JPS58204051A (ja) | 1983-11-28 |
| JPH0513993B2 JPH0513993B2 (en, 2012) | 1993-02-23 |
Family
ID=6163351
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58081053A Granted JPS58204051A (ja) | 1982-05-12 | 1983-05-11 | モノアゾ化合物及び該化合物を染料として使用する方法 |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0094055B1 (en, 2012) |
| JP (1) | JPS58204051A (en, 2012) |
| KR (1) | KR910006960B1 (en, 2012) |
| AR (1) | AR241411A1 (en, 2012) |
| BR (1) | BR8302503A (en, 2012) |
| CA (1) | CA1221360A (en, 2012) |
| DE (2) | DE3217812A1 (en, 2012) |
| IN (1) | IN157455B (en, 2012) |
| MX (1) | MX156077A (en, 2012) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63202667A (ja) * | 1987-02-14 | 1988-08-22 | ヘキスト・アクチエンゲゼルシヤフト | 水溶性アゾ化合物、その製法及び該化合物を染料として使用する方法 |
| JPH01279976A (ja) * | 1988-01-20 | 1989-11-10 | Sumitomo Chem Co Ltd | モノアゾ化合物およびそれを用いて繊維材料を染色又は捺染する方法 |
| JP2010031289A (ja) * | 2001-04-20 | 2010-02-12 | Clariant Finance Bvi Ltd | 繊維反応性モノアゾ染料 |
| CN102277011A (zh) * | 2011-06-17 | 2011-12-14 | 上海雅运纺织化工有限公司 | 红色活性染料组合物及其在纤维上的染色应用 |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3470169D1 (en) * | 1983-10-26 | 1988-05-05 | Ciba Geigy Ag | Reactive dyes, their preparation and their use |
| EP0177445B1 (de) * | 1984-09-26 | 1990-05-23 | Ciba-Geigy Ag | Reaktivfarbstoffe, deren Herstellung und Verwendung |
| DE3510179A1 (de) * | 1985-03-21 | 1986-09-25 | Hoechst Ag, 6230 Frankfurt | Wasserloesliche mono- und disazoverbindungen, verfahren zu deren herstellung und ihre verwendung als farbstoffe |
| DE3510180A1 (de) * | 1985-03-21 | 1986-09-25 | Hoechst Ag, 6230 Frankfurt | Wasserloesliche azoverbindungen, verfahren zu deren herstellung und ihre verwendung als farbstoffe |
| DE3624136A1 (de) * | 1985-09-30 | 1987-04-09 | Hoechst Ag | Wasserloesliche azoverbindungen, verfahren zu deren herstellung und ihre verwendung als farbstoffe |
| US5003053A (en) * | 1987-02-14 | 1991-03-26 | Hoechst Aktiengesellschaft | Water-soluble monoazo compounds containing a p-aminophenylamino- and chloro- or fluoro-substituted triazinylamino group and a fiber-reactive group selected from the vinylsulfone series, suitable as dyestuffs |
| US5037965A (en) * | 1987-12-01 | 1991-08-06 | Sumitomo Chemical Company, Limited | Monoazo red dye compound having vinylsulfone type fiber reactive groups |
| US5243034A (en) * | 1988-12-21 | 1993-09-07 | Hoechst Aktiengesellschaft | Disazo dyestuffs having a triazine moiety and a fiberreactive group of vinylsulfone series |
| GB9025018D0 (en) * | 1990-11-16 | 1991-01-02 | Ici Plc | Reactive dyes |
| MX9102026A (es) * | 1990-11-16 | 1992-06-01 | Ici Plc | Colorantes reactivos |
| GB9111427D0 (en) * | 1991-05-28 | 1991-07-17 | Ici Plc | Reactive dyes |
| EP0545219A1 (de) * | 1991-12-05 | 1993-06-09 | Bayer Ag | Reaktivfarbstoffe, deren Herstellung und Verwendung |
| US5330539A (en) * | 1991-12-18 | 1994-07-19 | Hoechst Celanese Corporation | Fiber reactive dyes - applications with low salt |
| DE4214740A1 (de) * | 1992-05-04 | 1993-11-11 | Bayer Ag | Reaktivfarbstoffe, deren Herstellung und Verwendung |
| DE4417719A1 (de) * | 1994-05-20 | 1995-11-23 | Hoechst Ag | Reaktivfarbstoffe mit hydrolysestabilen Reaktivgruppen |
| US5514717A (en) * | 1994-10-26 | 1996-05-07 | Monsanto Company | Fluoroalkenyl compounds and their use as pest control agents |
| DE4438544A1 (de) * | 1994-10-28 | 1996-05-02 | Bayer Ag | Verfahren zum Färben und Bedrucken von hydroxy- und/oder carbonamidgruppenhaltigen Materialien |
| DE4447276C2 (de) * | 1994-12-30 | 1998-08-27 | Dystar Textilfarben Gmbh & Co | Farbstoffmischung von wasserlöslichen faserreaktiven Azofarbstoffen, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19510135A1 (de) * | 1995-03-21 | 1996-09-26 | Bayer Ag | Monoazoreaktivfarbstoffe |
| DE19511688C2 (de) * | 1995-03-30 | 1999-07-22 | Dystar Textilfarben Gmbh & Co | Farbstoffmischungen von faserreaktiven Azofarbstoffen und ihre Verwendung zum Färben von hydroxy- und/oder carbonamidgruppenhaltigem Fasermaterial |
| US5980590A (en) * | 1995-12-28 | 1999-11-09 | Dystar Texilfarben Gmbh & Co. Deutschland Kg | Dyestuff mixtures of water-soluble fiber-reactive azo dyestuffs, processes for their preparation and their use |
| DE19635999A1 (de) | 1996-09-05 | 1998-03-12 | Dystar Textilfarben Gmbh & Co | Farbstoffmischungen von faserreaktiven Azofarbstoffen und ihre Verwendung zum Färben von hydroxy- und/oder carbonamidgruppenhaltigem Fasermaterial |
| DE19836661A1 (de) * | 1998-08-13 | 2000-02-17 | Dystar Textilfarben Gmbh & Co | Farbstoffmischung von wasserlöslichen faserreaktiven Azofarbstoffen, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US6086639A (en) * | 1999-03-09 | 2000-07-11 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Black dye mixtures of fiber-reactive azo dyes and use thereof for dyeing hydroxy- and/or carboxamido-containing fiber material |
| US6036732A (en) * | 1999-04-30 | 2000-03-14 | Dystar Textilfarben Gmbh & Co. Deuschland Kg | Black dye mixtures of fiber-reactive azo dyes, methods for their preparation and use thereof for dyeing hydroxy-and/or carboxamido-cont |
| US6391066B1 (en) * | 2000-02-23 | 2002-05-21 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Dye mixture comprising water-soluble fiber-reactive dyes, preparation thereof and use thereof |
| DE10017555A1 (de) | 2000-04-08 | 2001-10-11 | Dystar Textilfarben Gmbh & Co | Farbstoffmischung von wasserlöslichen faserreaktiven Azofarbstoffen, Verfahren zu ihrer Herstellung und ihre Verwendung |
| KR20030022303A (ko) | 2000-07-25 | 2003-03-15 | 다이스타 텍스틸파르벤 게엠베하 운트 컴파니 도이칠란트 카게 | 황색 반응성 모노아조 염료, 이의 제조 방법 및 이의 용도 |
| EP1247841B1 (de) * | 2001-04-03 | 2012-09-26 | Huntsman Advanced Materials (Switzerland) GmbH | Reaktivfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung |
| PT2536791T (pt) * | 2010-02-18 | 2017-08-04 | Huntsman Advanced Mat (Switzerland) Gmbh | Misturas de corantes fibrorreativos e sua utilização num processo de tingimento ou estampagem di ou tricromáticos |
| CN101914302B (zh) * | 2010-07-17 | 2016-01-06 | 青岛大学 | 一种k型活性耐光红色偶氮染料及其制备方法 |
| CN103554981A (zh) * | 2013-09-29 | 2014-02-05 | 天津德凯化工股份有限公司 | 一种红色活性染料 |
| CN103554980A (zh) * | 2013-09-29 | 2014-02-05 | 天津德凯化工股份有限公司 | 一种红色活性染料及制备方法 |
| CN103554976A (zh) * | 2013-09-29 | 2014-02-05 | 天津德凯化工股份有限公司 | 一种红色活性染料及其制备方法 |
| CN104262998B (zh) * | 2014-09-03 | 2015-09-30 | 蓬莱嘉信染料化工股份有限公司 | 常-中温下染色的红色活性染料及其复配混合物 |
| CN107532008A (zh) | 2015-05-12 | 2018-01-02 | 亨斯迈先进材料（瑞士）有限公司 | 反应性染料的混合物及其用于纺织纤维材料的染色或印刷的用途 |
| WO2021219556A1 (en) | 2020-04-27 | 2021-11-04 | Huntsman Advanced Materials (Switzerland) Gmbh | Mixtures of reactive dyes and their use for the dyeing or printing of textile fibre materials |
| PE20250124A1 (es) | 2022-01-25 | 2025-01-16 | Archroma Switzerland Gmbh | Mezcla isomerica de tintes reactivos y su uso para el tenido o estampado de materiales de fibra textil |
| CN116004032A (zh) * | 2022-12-30 | 2023-04-25 | 上海雅运新材料有限公司 | 一种红色染料化合物及其合成方法和应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1265698C2 (de) * | 1961-05-06 | 1968-11-07 | Hoechst Ag | Verfahren zur Erzeugung von nassechten Faerbungen und Drucken |
| CH627206A5 (en, 2012) * | 1978-07-06 | 1981-12-31 | Ciba Geigy Ag |
-
1982
- 1982-05-12 DE DE19823217812 patent/DE3217812A1/de not_active Withdrawn
-
1983
- 1983-03-10 AR AR83292979A patent/AR241411A1/es active
- 1983-05-05 IN IN561/CAL/83A patent/IN157455B/en unknown
- 1983-05-06 EP EP83104470A patent/EP0094055B1/de not_active Expired
- 1983-05-06 DE DE8383104470T patent/DE3368074D1/de not_active Expired
- 1983-05-10 KR KR1019830002010A patent/KR910006960B1/ko not_active Expired
- 1983-05-11 CA CA000427942A patent/CA1221360A/en not_active Expired
- 1983-05-11 MX MX197242A patent/MX156077A/es unknown
- 1983-05-11 JP JP58081053A patent/JPS58204051A/ja active Granted
- 1983-05-12 BR BR8302503A patent/BR8302503A/pt not_active IP Right Cessation
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63202667A (ja) * | 1987-02-14 | 1988-08-22 | ヘキスト・アクチエンゲゼルシヤフト | 水溶性アゾ化合物、その製法及び該化合物を染料として使用する方法 |
| JPH01279976A (ja) * | 1988-01-20 | 1989-11-10 | Sumitomo Chem Co Ltd | モノアゾ化合物およびそれを用いて繊維材料を染色又は捺染する方法 |
| JP2010031289A (ja) * | 2001-04-20 | 2010-02-12 | Clariant Finance Bvi Ltd | 繊維反応性モノアゾ染料 |
| CN102277011A (zh) * | 2011-06-17 | 2011-12-14 | 上海雅运纺织化工有限公司 | 红色活性染料组合物及其在纤维上的染色应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0513993B2 (en, 2012) | 1993-02-23 |
| AR241411A1 (es) | 1992-07-31 |
| EP0094055B1 (de) | 1986-12-03 |
| BR8302503A (pt) | 1984-01-17 |
| IN157455B (en, 2012) | 1986-04-05 |
| DE3217812A1 (de) | 1983-11-17 |
| KR910006960B1 (ko) | 1991-09-14 |
| CA1221360A (en) | 1987-05-05 |
| KR840004766A (ko) | 1984-10-24 |
| MX156077A (es) | 1988-06-14 |
| DE3368074D1 (en) | 1987-01-15 |
| EP0094055A1 (de) | 1983-11-16 |
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