GB2024235A - Water-insoluble azo dyestuffs, process for their manufacture and their use - Google Patents
Water-insoluble azo dyestuffs, process for their manufacture and their use Download PDFInfo
- Publication number
- GB2024235A GB2024235A GB7920036A GB7920036A GB2024235A GB 2024235 A GB2024235 A GB 2024235A GB 7920036 A GB7920036 A GB 7920036A GB 7920036 A GB7920036 A GB 7920036A GB 2024235 A GB2024235 A GB 2024235A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dyestuff
- alkyl
- carbon atoms
- formula
- cellulose
- 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
- 238000000034 method Methods 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- -1 chlorobenzoyl Chemical group 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims abstract description 8
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims abstract description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 125000001424 substituent group Chemical group 0.000 claims abstract description 4
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims abstract description 4
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 claims abstract description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims abstract description 3
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 239000000460 chlorine Substances 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- 239000011737 fluorine Substances 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims abstract description 3
- 125000000542 sulfonic acid group Chemical group 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 239000000975 dye Substances 0.000 claims description 19
- 230000008878 coupling Effects 0.000 claims description 12
- 238000010168 coupling process Methods 0.000 claims description 12
- 238000005859 coupling reaction Methods 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 239000002657 fibrous material Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 229920000728 polyester Polymers 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 238000004043 dyeing Methods 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 239000004952 Polyamide Substances 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 229920002647 polyamide Polymers 0.000 claims description 6
- 229920002284 Cellulose triacetate Polymers 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 claims description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- 229920001747 Cellulose diacetate Polymers 0.000 claims description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 3
- VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 229920000515 polycarbonate Polymers 0.000 claims description 3
- 239000004417 polycarbonate Substances 0.000 claims description 3
- 229920002635 polyurethane Polymers 0.000 claims description 3
- 239000004814 polyurethane Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000001632 sodium acetate Substances 0.000 claims description 3
- 235000017281 sodium acetate Nutrition 0.000 claims description 3
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 150000002473 indoazoles Chemical class 0.000 claims description 2
- 239000000395 magnesium oxide Substances 0.000 claims description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 229920002678 cellulose Polymers 0.000 claims 2
- 239000001913 cellulose Substances 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract description 2
- 125000001246 bromo group Chemical group Br* 0.000 abstract description 2
- 150000002923 oximes Chemical class 0.000 abstract description 2
- 125000003453 indazolyl group Chemical class N1N=C(C2=C1C=CC=C2)* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- MIHADVKEHAFNPG-UHFFFAOYSA-N 2-Amino-5-nitrothiazole Chemical compound NC1=NC=C([N+]([O-])=O)S1 MIHADVKEHAFNPG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- COEZWFYORILMOM-UHFFFAOYSA-N sodium 4-[(2,4-dihydroxyphenyl)diazenyl]benzenesulfonic acid Chemical compound [Na+].OC1=CC(O)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 COEZWFYORILMOM-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- 229940018167 2-amino-5-nitrothiazole Drugs 0.000 description 2
- KWMDHCLJYMVBNS-UHFFFAOYSA-N 2-bromo-4,6-dinitroaniline Chemical compound NC1=C(Br)C=C([N+]([O-])=O)C=C1[N+]([O-])=O KWMDHCLJYMVBNS-UHFFFAOYSA-N 0.000 description 2
- CGPPWNTVTNCHDO-UHFFFAOYSA-N 2-bromo-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Br CGPPWNTVTNCHDO-UHFFFAOYSA-N 0.000 description 2
- LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 description 2
- XTTIQGSLJBWVIV-UHFFFAOYSA-N 2-methyl-4-nitroaniline Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N XTTIQGSLJBWVIV-UHFFFAOYSA-N 0.000 description 2
- YBAZINRZQSAIAY-UHFFFAOYSA-N 4-aminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1 YBAZINRZQSAIAY-UHFFFAOYSA-N 0.000 description 2
- GPNAVOJCQIEKQF-UHFFFAOYSA-N 6-nitro-1,3-benzothiazol-2-amine Chemical compound C1=C([N+]([O-])=O)C=C2SC(N)=NC2=C1 GPNAVOJCQIEKQF-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000234314 Zingiber Species 0.000 description 2
- 235000006886 Zingiber officinale Nutrition 0.000 description 2
- 230000001464 adherent effect Effects 0.000 description 2
- 229960004050 aminobenzoic acid Drugs 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N aniline-p-carboxylic acid Natural products NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 235000008397 ginger Nutrition 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 239000012209 synthetic fiber Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 1
- FUADXEJBHCKVBN-UHFFFAOYSA-N (3-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 FUADXEJBHCKVBN-UHFFFAOYSA-N 0.000 description 1
- RBKHNGHPZZZJCI-UHFFFAOYSA-N (4-aminophenyl)-phenylmethanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC=C1 RBKHNGHPZZZJCI-UHFFFAOYSA-N 0.000 description 1
- QUKGLNCXGVWCJX-UHFFFAOYSA-N 1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=CS1 QUKGLNCXGVWCJX-UHFFFAOYSA-N 0.000 description 1
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
- GPRYKVSEZCQIHD-UHFFFAOYSA-N 1-(4-aminophenyl)ethanone Chemical compound CC(=O)C1=CC=C(N)C=C1 GPRYKVSEZCQIHD-UHFFFAOYSA-N 0.000 description 1
- YDTDKKULPWTHRV-UHFFFAOYSA-N 1H-indazol-3-amine Chemical compound C1=CC=C2C(N)=NNC2=C1 YDTDKKULPWTHRV-UHFFFAOYSA-N 0.000 description 1
- AZXGXVQWEUFULR-UHFFFAOYSA-N 2',4',5',7'-tetrabromofluorescein Chemical compound OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 AZXGXVQWEUFULR-UHFFFAOYSA-N 0.000 description 1
- GUMCAKKKNKYFEB-UHFFFAOYSA-N 2,4,5-trichloroaniline Chemical compound NC1=CC(Cl)=C(Cl)C=C1Cl GUMCAKKKNKYFEB-UHFFFAOYSA-N 0.000 description 1
- GVPODVKBTHCGFU-UHFFFAOYSA-N 2,4,6-tribromoaniline Chemical compound NC1=C(Br)C=C(Br)C=C1Br GVPODVKBTHCGFU-UHFFFAOYSA-N 0.000 description 1
- NATVSFWWYVJTAZ-UHFFFAOYSA-N 2,4,6-trichloroaniline Chemical compound NC1=C(Cl)C=C(Cl)C=C1Cl NATVSFWWYVJTAZ-UHFFFAOYSA-N 0.000 description 1
- IAHOUQOWMXVMEH-UHFFFAOYSA-N 2,4,6-trinitroaniline Chemical compound NC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O IAHOUQOWMXVMEH-UHFFFAOYSA-N 0.000 description 1
- DYSRXWYRUJCNFI-UHFFFAOYSA-N 2,4-dibromoaniline Chemical compound NC1=CC=C(Br)C=C1Br DYSRXWYRUJCNFI-UHFFFAOYSA-N 0.000 description 1
- IZEZAMILKKYOPW-UHFFFAOYSA-N 2,4-dichloro-6-nitroaniline Chemical compound NC1=C(Cl)C=C(Cl)C=C1[N+]([O-])=O IZEZAMILKKYOPW-UHFFFAOYSA-N 0.000 description 1
- KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 description 1
- VBXPHDBFAZDZOB-UHFFFAOYSA-N 2,4-dinitro-6-(trifluoromethyl)aniline Chemical compound NC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1C(F)(F)F VBXPHDBFAZDZOB-UHFFFAOYSA-N 0.000 description 1
- LXQOQPGNCGEELI-UHFFFAOYSA-N 2,4-dinitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O LXQOQPGNCGEELI-UHFFFAOYSA-N 0.000 description 1
- WRTAZRGRFBCKBU-UHFFFAOYSA-N 2,5-dibromoaniline Chemical compound NC1=CC(Br)=CC=C1Br WRTAZRGRFBCKBU-UHFFFAOYSA-N 0.000 description 1
- AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 1
- YMZIFDLWYUSZCC-UHFFFAOYSA-N 2,6-dibromo-4-nitroaniline Chemical compound NC1=C(Br)C=C([N+]([O-])=O)C=C1Br YMZIFDLWYUSZCC-UHFFFAOYSA-N 0.000 description 1
- JDMFXJULNGEPOI-UHFFFAOYSA-N 2,6-dichloroaniline Chemical compound NC1=C(Cl)C=CC=C1Cl JDMFXJULNGEPOI-UHFFFAOYSA-N 0.000 description 1
- VBLXCTYLWZJBKA-UHFFFAOYSA-N 2-(trifluoromethyl)aniline Chemical group NC1=CC=CC=C1C(F)(F)F VBLXCTYLWZJBKA-UHFFFAOYSA-N 0.000 description 1
- KWAXPNSWICZXMJ-UHFFFAOYSA-N 2-[(2-amino-3,5-dinitrophenyl)methylsulfonylmethyl]-4,6-dinitroaniline Chemical compound C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C(N)=C1CS(=O)(=O)CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1N KWAXPNSWICZXMJ-UHFFFAOYSA-N 0.000 description 1
- ALLKCOXKRSYQLQ-UHFFFAOYSA-N 2-[(2-amino-3-bromo-5-nitrophenyl)methylsulfonylmethyl]-6-bromo-4-nitroaniline Chemical compound NC1=C(C=C(C=C1Br)[N+](=O)[O-])CS(=O)(=O)CC1=C(C(=CC(=C1)[N+](=O)[O-])Br)N ALLKCOXKRSYQLQ-UHFFFAOYSA-N 0.000 description 1
- FYXJXUMICYGRKV-UHFFFAOYSA-N 2-[(2-amino-5-nitrophenyl)methylsulfonylmethyl]-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1CS(=O)(=O)CC1=CC([N+]([O-])=O)=CC=C1N FYXJXUMICYGRKV-UHFFFAOYSA-N 0.000 description 1
- GDFCZZHSWGWCHP-UHFFFAOYSA-N 2-amino-1,3-benzothiazole-6-carbonitrile Chemical compound C1=C(C#N)C=C2SC(N)=NC2=C1 GDFCZZHSWGWCHP-UHFFFAOYSA-N 0.000 description 1
- YJTBHWXNEMGNDC-UHFFFAOYSA-N 2-amino-1,3-thiazole-5-carbonitrile Chemical compound NC1=NC=C(C#N)S1 YJTBHWXNEMGNDC-UHFFFAOYSA-N 0.000 description 1
- HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical compound NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 description 1
- RIYSFSQPHCAGLS-UHFFFAOYSA-N 2-amino-3,5-dinitrobenzonitrile Chemical compound NC1=C(C#N)C=C([N+]([O-])=O)C=C1[N+]([O-])=O RIYSFSQPHCAGLS-UHFFFAOYSA-N 0.000 description 1
- NWJVVECYUHZQEU-UHFFFAOYSA-N 2-amino-3-[(2-amino-3-cyano-5-nitrophenyl)methylsulfonylmethyl]-5-nitrobenzonitrile Chemical compound NC1=C(C=C(C=C1C#N)[N+](=O)[O-])CS(=O)(=O)CC1=C(C(=CC(=C1)[N+](=O)[O-])C#N)N NWJVVECYUHZQEU-UHFFFAOYSA-N 0.000 description 1
- XVYNBLCPQVDRCH-UHFFFAOYSA-N 2-amino-3-chloro-5-nitrobenzonitrile Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1C#N XVYNBLCPQVDRCH-UHFFFAOYSA-N 0.000 description 1
- MITPJFSBGKMNGU-UHFFFAOYSA-N 2-amino-3-methoxy-5-nitrobenzonitrile Chemical compound COC1=CC([N+]([O-])=O)=CC(C#N)=C1N MITPJFSBGKMNGU-UHFFFAOYSA-N 0.000 description 1
- MGCGMYPNXAFGFA-UHFFFAOYSA-N 2-amino-5-nitrobenzonitrile Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C#N MGCGMYPNXAFGFA-UHFFFAOYSA-N 0.000 description 1
- IXNKCWJILKDDBZ-UHFFFAOYSA-N 2-aminobenzene-1,4-dicarbonitrile Chemical compound NC1=CC(C#N)=CC=C1C#N IXNKCWJILKDDBZ-UHFFFAOYSA-N 0.000 description 1
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 1
- AOPBDRUWRLBSDB-UHFFFAOYSA-N 2-bromoaniline Chemical compound NC1=CC=CC=C1Br AOPBDRUWRLBSDB-UHFFFAOYSA-N 0.000 description 1
- LHRIICYSGQGXSX-UHFFFAOYSA-N 2-chloro-4,6-dinitroaniline Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1[N+]([O-])=O LHRIICYSGQGXSX-UHFFFAOYSA-N 0.000 description 1
- MFJODFSUXHFZJR-UHFFFAOYSA-N 2-chloro-4-nitro-6-(trifluoromethyl)aniline Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1C(F)(F)F MFJODFSUXHFZJR-UHFFFAOYSA-N 0.000 description 1
- YRAOKFMNBZXHOM-UHFFFAOYSA-N 2-chloro-6-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC(Cl)=C1N YRAOKFMNBZXHOM-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical group NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- FTZQXOJYPFINKJ-UHFFFAOYSA-N 2-fluoroaniline Chemical group NC1=CC=CC=C1F FTZQXOJYPFINKJ-UHFFFAOYSA-N 0.000 description 1
- XLJMDBOKSZROPC-UHFFFAOYSA-N 2-methoxy-4,6-dinitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1N XLJMDBOKSZROPC-UHFFFAOYSA-N 0.000 description 1
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 1
- ATXBGHLILIABGX-UHFFFAOYSA-N 2-nitro-4-(trifluoromethyl)aniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O ATXBGHLILIABGX-UHFFFAOYSA-N 0.000 description 1
- DLURHXYXQYMPLT-UHFFFAOYSA-N 2-nitro-p-toluidine Chemical compound CC1=CC=C(N)C([N+]([O-])=O)=C1 DLURHXYXQYMPLT-UHFFFAOYSA-N 0.000 description 1
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
- CKQHAYFOPRIUOM-UHFFFAOYSA-N 3'-Aminoacetophenone Chemical compound CC(=O)C1=CC=CC(N)=C1 CKQHAYFOPRIUOM-UHFFFAOYSA-N 0.000 description 1
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 1
- VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical group NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 description 1
- DHYHYLGCQVVLOQ-UHFFFAOYSA-N 3-bromoaniline Chemical compound NC1=CC=CC(Br)=C1 DHYHYLGCQVVLOQ-UHFFFAOYSA-N 0.000 description 1
- QNAAQOLWUDNQFY-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1.NC1=CC=CC(Cl)=C1 QNAAQOLWUDNQFY-UHFFFAOYSA-N 0.000 description 1
- QZVQQUVWFIZUBQ-UHFFFAOYSA-N 3-fluoroaniline Chemical compound NC1=CC=CC(F)=C1 QZVQQUVWFIZUBQ-UHFFFAOYSA-N 0.000 description 1
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- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- QIKYZXDTTPVVAC-UHFFFAOYSA-N 4-Aminobenzamide Chemical compound NC(=O)C1=CC=C(N)C=C1 QIKYZXDTTPVVAC-UHFFFAOYSA-N 0.000 description 1
- JIIQWIZQMHZHLL-UHFFFAOYSA-N 4-[(4-amino-3-nitrophenyl)methylsulfonylmethyl]-2-nitroaniline Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1CS(=O)(=O)CC1=CC=C(N)C([N+]([O-])=O)=C1 JIIQWIZQMHZHLL-UHFFFAOYSA-N 0.000 description 1
- FWTBRYBHCBCJEQ-UHFFFAOYSA-N 4-[(4-phenyldiazenylnaphthalen-1-yl)diazenyl]phenol Chemical compound C1=CC(O)=CC=C1N=NC(C1=CC=CC=C11)=CC=C1N=NC1=CC=CC=C1 FWTBRYBHCBCJEQ-UHFFFAOYSA-N 0.000 description 1
- JAHADAZIDZMHOP-UHFFFAOYSA-N 4-amino-3-nitrobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1[N+]([O-])=O JAHADAZIDZMHOP-UHFFFAOYSA-N 0.000 description 1
- BABGMPQXLCJMSK-UHFFFAOYSA-N 4-amino-n,n-dimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=C(N)C=C1 BABGMPQXLCJMSK-UHFFFAOYSA-N 0.000 description 1
- IPMNLGOBXWTQRV-UHFFFAOYSA-N 4-aminobenzene-1,3-dicarbonitrile Chemical compound NC1=CC=C(C#N)C=C1C#N IPMNLGOBXWTQRV-UHFFFAOYSA-N 0.000 description 1
- ZCWBZRBJSPWUPG-UHFFFAOYSA-N 4-bromo-2-nitroaniline Chemical compound NC1=CC=C(Br)C=C1[N+]([O-])=O ZCWBZRBJSPWUPG-UHFFFAOYSA-N 0.000 description 1
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- PBGKNXWGYQPUJK-UHFFFAOYSA-N 4-chloro-2-nitroaniline Chemical compound NC1=CC=C(Cl)C=C1[N+]([O-])=O PBGKNXWGYQPUJK-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 1
- QFMJFXFXQAFGBO-UHFFFAOYSA-N 4-methoxy-2-nitroaniline Chemical compound COC1=CC=C(N)C([N+]([O-])=O)=C1 QFMJFXFXQAFGBO-UHFFFAOYSA-N 0.000 description 1
- XJEVFFNOMKXBLU-UHFFFAOYSA-N 4-methylsulfonylaniline Chemical compound CS(=O)(=O)C1=CC=C(N)C=C1 XJEVFFNOMKXBLU-UHFFFAOYSA-N 0.000 description 1
- HOTZLWVITTVZGY-UHFFFAOYSA-N 4-nitro-2-(trifluoromethyl)aniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(F)(F)F HOTZLWVITTVZGY-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- WOYZXEVUWXQVNV-UHFFFAOYSA-N 4-phenoxyaniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC=C1 WOYZXEVUWXQVNV-UHFFFAOYSA-N 0.000 description 1
- QPQKUYVSJWQSDY-UHFFFAOYSA-N 4-phenyldiazenylaniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=CC=C1 QPQKUYVSJWQSDY-UHFFFAOYSA-N 0.000 description 1
- ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 description 1
- SQBCSDZTDXLTLE-UHFFFAOYSA-N 5-nitro-2,1-benzothiazol-3-amine Chemical compound C1=CC([N+]([O-])=O)=CC2=C(N)SN=C21 SQBCSDZTDXLTLE-UHFFFAOYSA-N 0.000 description 1
- FUARCQLZUVMPSL-UHFFFAOYSA-N 5-nitro-2h-1,3-benzothiazol-3-amine Chemical compound C1=C([N+]([O-])=O)C=C2N(N)CSC2=C1 FUARCQLZUVMPSL-UHFFFAOYSA-N 0.000 description 1
- VMNXKIDUTPOHPO-UHFFFAOYSA-N 6-chloro-1,3-benzothiazol-2-amine Chemical compound C1=C(Cl)C=C2SC(N)=NC2=C1 VMNXKIDUTPOHPO-UHFFFAOYSA-N 0.000 description 1
- KZHGPDSVHSDCMX-UHFFFAOYSA-N 6-methoxy-1,3-benzothiazol-2-amine Chemical compound COC1=CC=C2N=C(N)SC2=C1 KZHGPDSVHSDCMX-UHFFFAOYSA-N 0.000 description 1
- DZWTXWPRWRLHIL-UHFFFAOYSA-N 6-methyl-1,3-benzothiazol-2-amine Chemical compound CC1=CC=C2N=C(N)SC2=C1 DZWTXWPRWRLHIL-UHFFFAOYSA-N 0.000 description 1
- ZYHNHJAMVNINSY-UHFFFAOYSA-N 6-methylsulfonyl-1,3-benzothiazol-2-amine Chemical compound CS(=O)(=O)C1=CC=C2N=C(N)SC2=C1 ZYHNHJAMVNINSY-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- TWLLPUMZVVGILS-UHFFFAOYSA-N Ethyl 2-aminobenzoate Chemical compound CCOC(=O)C1=CC=CC=C1N TWLLPUMZVVGILS-UHFFFAOYSA-N 0.000 description 1
- HSUXNXBMGKNJBA-UHFFFAOYSA-N N#CC1=CC=CC(C#N)=C1N[N+]([O-])=O Chemical compound N#CC1=CC=CC(C#N)=C1N[N+]([O-])=O HSUXNXBMGKNJBA-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FHNINJWBTRXEBC-UHFFFAOYSA-N Sudan III Chemical compound OC1=CC=C2C=CC=CC2=C1N=NC(C=C1)=CC=C1N=NC1=CC=CC=C1 FHNINJWBTRXEBC-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- ZMJPCIAEJKVKMQ-UHFFFAOYSA-M [4-[[4-[benzyl(methyl)amino]phenyl]-[4-(dimethylamino)phenyl]methylidene]cyclohexa-2,5-dien-1-ylidene]-dimethylazanium;chloride Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)CC=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 ZMJPCIAEJKVKMQ-UHFFFAOYSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 1
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000010014 continuous dyeing Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- BIXZHMJUSMUDOQ-UHFFFAOYSA-N dichloran Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl BIXZHMJUSMUDOQ-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- VNZXERIGKZNEKB-UHFFFAOYSA-N ethyl 2-amino-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(N)S1 VNZXERIGKZNEKB-UHFFFAOYSA-N 0.000 description 1
- AMLDNINFPSEDHZ-UHFFFAOYSA-N ethyl 2-amino-5-nitrobenzoate Chemical compound CCOC(=O)C1=CC([N+]([O-])=O)=CC=C1N AMLDNINFPSEDHZ-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 244000144992 flock Species 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- BLVZXLIGARVLJC-UHFFFAOYSA-N methyl 2-amino-3,5-dinitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1N BLVZXLIGARVLJC-UHFFFAOYSA-N 0.000 description 1
- SZTFIWRZGDLJNR-UHFFFAOYSA-N methyl 2-amino-3-bromo-4-nitrobenzoate Chemical compound COC(=O)C1=CC=C([N+]([O-])=O)C(Br)=C1N SZTFIWRZGDLJNR-UHFFFAOYSA-N 0.000 description 1
- DAWZEKCPPREGID-UHFFFAOYSA-N methyl 2-amino-3-cyano-5-nitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=CC(C#N)=C1N DAWZEKCPPREGID-UHFFFAOYSA-N 0.000 description 1
- YFKDXEODRNOFRA-UHFFFAOYSA-N methyl 2-amino-3-methoxy-5-nitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=CC(OC)=C1N YFKDXEODRNOFRA-UHFFFAOYSA-N 0.000 description 1
- VOQBLPBLKSXCDB-UHFFFAOYSA-N methyl 2-amino-5-nitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=CC=C1N VOQBLPBLKSXCDB-UHFFFAOYSA-N 0.000 description 1
- VZDNXXPBYLGWOS-UHFFFAOYSA-N methyl 3-aminobenzoate Chemical compound COC(=O)C1=CC=CC(N)=C1 VZDNXXPBYLGWOS-UHFFFAOYSA-N 0.000 description 1
- LZXXNPOYQCLXRS-UHFFFAOYSA-N methyl 4-aminobenzoate Chemical compound COC(=O)C1=CC=C(N)C=C1 LZXXNPOYQCLXRS-UHFFFAOYSA-N 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- HHHDEYQZODHHKT-UHFFFAOYSA-N n-(2-amino-5-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC([N+]([O-])=O)=CC=C1N HHHDEYQZODHHKT-UHFFFAOYSA-N 0.000 description 1
- CHMBIJAOCISYEW-UHFFFAOYSA-N n-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 description 1
- YNTVUIMHMDCDHR-UHFFFAOYSA-N n-[(4-aminophenyl)methylidene]hydroxylamine Chemical compound NC1=CC=C(C=NO)C=C1 YNTVUIMHMDCDHR-UHFFFAOYSA-N 0.000 description 1
- ILCQYORZHHFLNL-UHFFFAOYSA-N n-bromoaniline Chemical compound BrNC1=CC=CC=C1 ILCQYORZHHFLNL-UHFFFAOYSA-N 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
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- VSXGXPNADZQTGQ-UHFFFAOYSA-N oxirane;phenol Chemical compound C1CO1.OC1=CC=CC=C1 VSXGXPNADZQTGQ-UHFFFAOYSA-N 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- HGRXBNZHQKXDPL-UHFFFAOYSA-N phenyl 4-aminobenzoate Chemical compound C1=CC(N)=CC=C1C(=O)OC1=CC=CC=C1 HGRXBNZHQKXDPL-UHFFFAOYSA-N 0.000 description 1
- GVKCHTBDSMQENH-UHFFFAOYSA-L phloxine B Chemical compound [Na+].[Na+].[O-]C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 GVKCHTBDSMQENH-UHFFFAOYSA-L 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010025 steaming Methods 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
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- ZMCBYSBVJIMENC-UHFFFAOYSA-N tricaine Chemical compound CCOC(=O)C1=CC=CC(N)=C1 ZMCBYSBVJIMENC-UHFFFAOYSA-N 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000002759 woven fabric 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
- C09B29/0815—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by -C(=O)-
- C09B29/0816—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by -C(=O)- substituted by -COOR
-
- 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/04—Disazo dyes from a coupling component "C" containing a directive amino group
- C09B31/043—Amino-benzenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The present invention provides water-insoluble azo dyestuffs of the general formula (I> <IMAGE> wherein D represents the radical of a diazo component of the benzene, azobenzene, naphthalene, thiazole, benzothiazole, thiadiazole, benzisothiazole or indazole series, which is free from sulfonic acid groups and in which the ring or each ring independently is unsubstituted or substituted by one or more substituents selected from halogen atoms, for example fluorine, chlorine and bromine atoms, and nitro, cyano, alkyl, alkoxy, alkylsulfonyl, sulfonamido, trifluoromethyl, alkycarbonyl, chloralkylcarbonyl, alkylcarbonylamino, chloroalkylcarbonylamino, benzoyl, chlorobenzoyl, benzoylamino, chlorobenzoylamino, phenoxy, oxime, carboxylic acid alkyl ester and carboxylic acid amide groups, the alkyl and alkoxy groups and moieties each having from 1 to 4 carbon atoms, R1 and R2, which may be the same or different, each represents an alkyl group having from 1 to 4 carbon atoms, and R3 represents a hydrogen atom or an alkyl or alkoxy group having from 1 to 4 carbon atoms.
Description
SPECIFICATION
Water-insoluble azo dyestuffs, process for their manufacture and their use.
The present invention provides water-insoluble azo dyestuffs of the general formula (I)
wherein D represents the radical of a diazo component of the benzene, azobenzene, napthalene, thiazole, benzothiazole, thiadiazole, benzisothiazole or indazole series, which is free from sulfonic acid groups and in which the ring or each ring independently is unsubstituted or substituted by one or more substituents selected from halogen atoms, for example fluorine, chlorine and bromine atoms, and nitro, cyano, alkyl, alkoxy, alkylsulfonyl, sulfonamido, trifluoromethyl, alkylcarbonyl, chloroalkylcarbonyl, alkylcarbonylamino, chloroalkylcarbonylamino, benzoyl, chlorobenzoyl, benzoylamino, chlorobenzoylamino, phenoxy, oxime, carboxylic acid alkly ester and carboxylic acid amide groups, the alkyl and alkoxy groups and moieties each having from 1 to 4 carbon atoms,
R1 and R2, which may be the same or different, each represents an alkyl group having from 1 to 4 carbon atoms, and
R3 represents a hydrogen atom or an alkyl or alkoxy group having from 1 to 4 carbon atoms.
The present invention also provides a process for the manufacture of the above dyestuffs, which comprises diazotizing in known manner a diazo component of the general formula (II) D- NH2 (II) wherein D is defined as above, and coupling the resulting product with a coupling component of the general formula (III)
wherein R1, R2 and R3 are defined as above, in an acidic or neutral, aqueous, aqueous-organic or organic medium, preferably an aqueous medium, and optionally in the presence of an acid-binding agent.
As organic solvents which may be used there may be mentioned hydrophilic organic solvents, for example methanol, ethanol, propanol, butanol, acetone or dimethylformamide.
As acid-binding agents which may be present during coupling there may be mentioned organic bases such as pyridine, picoline ortriethylamine, and inorganic bases such as alkali metal and alkaline earth metal carbonates, for example sodium or potassium carbonate, or magnesium oxide, or particular sodium acetate.
The coupling components of the formula (III) may be prepared in simple manner by reacting an alkylerylamine of the formula (IV)
wherein R2 and R3 are defined as above, with an itaconic acidester of the formula (V)
wherein R1 is defined as above, in the presence of a catalyst for accelerating the reaction, such as acetic acid or hydrochloric acid, at an elevated temperature and optionally under elevated pressure.
As examples of diazo components of the general formula D-NH2. for preparation of the dyestuffs of the formula (I), there may be mentioned: aniline, p-toluidine, o-anisidine, m-anisidine, p-anisidine, p-phenetidine, p-phenoxyaniline, 2-fluoro, 3 fluoro- and 4-fluoroaniline, 2-chloro, 3-chloro- and 4-chloroaniline, 2-bromo-, 3-bromo- and 4-bromoaniline, 2-trifluoro-methyl-, 3-trifluoromethyl- and 4-trifluoromethylaniline, anthranilic acid methyl ester, anthranilic acid ethyl ester, 3-aminobenzoic acid methyl ester, 3-aminobenzoic acid ethyl ester, 4-aminobenzoic acid methyl ester, 4-aminobenzoic acid ethyl ester, 4-aminobenzoic acid phenyl ester, 4-aminobenzoic acid amide, 2-amino-, 3-amino- and 4-aminophenyl- methylsulfone, 4-aminophenylethlsulfone, 2-amino-, 3-amino- and 4-aminophenylsulfonamide, 4-aminophenylsulfonic acid dimethylamide, 2-amino-, 3-aminoand 4-aminobenzonitrile, 2-amino-, 3-amino- and 4-aminoacetophenone, 2-amino-, 3-amino- and 4aminobenzophenone, 2-nitro-, 3-nitro- and 4-nitroaniline, 2-acetamino-, 3-acetamino- and 4acetaminoaniline, 2-methyl-4-nitroaniline, 2-methoxy-4-nitroaniline, 2-chloro-4-nitroaniline, 2-bromo-4nitroaniline, 2-amino-5-nitrobenzoic acid methyl ester and 2-amino-5-nitrobenzoic acid ethyl ester, 2-amino-5-nitrophenylmethylsulfone, 2-amino-5-n itrophenylsulfonic acid amide, 2-cyano-4-nitroaniline, 4-aminobenzaldoxime, 2-acetamino-4-nitroaniline, 2-trifluoromethyl-4-nitroaniline, 2,6-dichloro-4nitroaniline, 2-chloro-4-nitro-6-methoxyaniline, 2-amino-3-chloro-5-nitribenzoic acid methyl ester, 2-amino 3-chloro-5-nitro-phenylmethylsulfone, 2-chloro-4-nitro-6-cyanoaniline, 2-chloro-4,6-dinitroaniline, 2-chloro 4-nitro-6-trifluoro-methylaniline, 2-ch loro-4-nitro-6-bromoa niline, 2-amino-3-methoxy-5-nitrobenzoic acid methyl ester, 2-methoxy-4-nitro-6-cyanoaniline, 2-methoxy-4,6-di-nitroaniline, 2-amino-3-cyano-5 nitrobenzoicacid methyl ester, 2-amino-3,5-di-nitrobenzoic acid methyl ester, 2-amino-3-bromo-4-nitrobenzoic acid methyl ester, 2-amino-3-cyano-5-nitrophenylmethyl-sulfone, 2-amino-3,5-dinitrophenylmethylsulfone, 2-amino-3-bromo-5-nitrophenylmethylsulfone, 2,6-di-cyano-nitroaniline, 2cyano-4, 6-dinitroaniline, 2-cyano-4-nitro-6-trifluoro-methylaniline, 2-cyane-4-nitro-6-bromaniline, 2,4,6-trinitroaniline, 2,4-di-nitro-6-trifluoromethylaniline, 2-bromo-4,6-di-nitroaniline, 2,6-di-bromo-4-nitroaniline, 2,4-di-chloroaniline, 2,4-di-bromoaniline, 2,4-dicyanoaniline, 2,4-di-nitroaniline, 2,5-di-chloroaniline, 2,5-dibromoaniline, 2,5-di-cyanoaniline, 2-aminotherephthalic acid methyl ester, 3,4-di-chloroaniline, 2,6-di chloroaniline, 4-methyl-2-nitroaniline, 4-methoxy-2-nitroaniline, 4-chloro-2-nitro-aniline, 4-bromo-2nitroaniline, 4-cyano-2-nitroaniline, 4-trifluoromethyl-2-nitroaniline, 4-amino-3-nitrophenyl-methylsulfone, 2,4,6-trichloroaniline, 2,4,5-trichloroaniline, 2,4-dichloro-6-nitroaniline, 2,4,6-tribromoaniline, 4phenylazoaniline, 2-aminothiazole, 5-nitro-2-aminothiazole, 5-ethoxycarbonyl-2-aminothiazole, 5-cyano-2aminothiazole, 2-aminobenzothiazole, 6-methyl-2-aminobenzothiazole, 6-methoxy-2-aminobenzothiazole, 6-cyano-2-aminobenzothiazole, 6-nitro-2-aminobenzothiazole, 6-methylsulfonyl-2-amino-benzothiazole, 6chloro-2-aminobenzothiazole, 2-amino-1 ,3,4-thiadiazole, 3-amino-5-nitro-2,1 -benzoisothiazole and 3aminoindazole.
The dyestuffs according to the invention are insoluble in water. They may be separated, for example, by filtration and they may be freed from adherent electrolyte by washing with water.
In the process of the invention either a single diazo component or a mixture of two or more diazo components of the formula (it), and either a single coupling component or a mixture of two or more coupling components of the formula (III), may be used.
The dyestuffs according to the invention may be used alone or in admixture with one another or with other dyestuffs. They are preferably used in the form of a dyeing or printing preparation, for example an aqueous dispersion, a solution in an organic solvent, or an emulsion or dispersion which may contain water in addition to a solvent or a mixture of solvents. The dyestuffs according to the invention may be used for dyeing or printing synthetic fibrous materials, for example fibers of cellulose-diacetate, cellulose-21/2 acetate or cellulose triacetate, polyamides such as poly-s-caprolactam or polyhexamethylenediamineadipate, polyurethanes, polycarbonates, or especially linear polyesters such as polythlene terephthalate.
The above-mentioned synthetic fibrous materials may be present in the form of blends of fibers of two or more of the above materials or blends with natural fibers such as cellulose fibers or wool. They may further be present in various processing states, for example as tops, flocks, filaments, woven fabrics or knitted fabrics.
The dyestuffs according to the invention may be applied in known manner, generally in an aqueous dispersion or alternatively in an organic solvent. Dispersion of the dyestuff may be carried out by grinding it in the presence of a dispersion agent, for example a condensation product of formaldehyde with a naphthalenesulfonic acid. The actual dyeing conditions may vary widely and depend on the nature of the synthetic fibrous material and on its process state.
For example, the dyeing of shaped articles of cellulose acetate is generally carried out at a temperature in the range of from about 75" to 85 , and that of cellulose triacetate articles at a temperature in the range of from about 90" to 1 250C. The dyestuffs are applied to polyamide fiber materials at a temperature in the range of from about 900 to 1200C.Polyester fiber materials are dyed according to usual methods, in the presence of a carrier such as o- or p-phenylphenol, methylnaphthalene or methylsalicylate, at a temperature from about 10000 up to about 130"C, or without the use of a carrier at a correspondingly higher temperature, for example in the range of from 1200 to 140"C. Alternatively, the dyestuffs may be applied by padding with or without the use of thickeners, such as a tragacanth thickener, followed by fixation under the action of heat, for example steam or dry heat, for a period from about half a minute to 30 minutes, at a temperature from about 1000 to 230"C. For improving the fastness to rubbing, the dyed material is advantageously freed from superficially adherent dyestuff, for example by flushing or by a reductive aftertreatment. The aftertreatment is carried out generally at 60 to 1 200C in a liquor containing aqueous sodium hydroxide solution, sodium dithionite and a non-ionogenic detergent such as an ethylene oxide-phenol addition product.
For dyeing synthetic fiber materials from organic solvents, the dyestuff is left in the solution for absorption on the fiber at room temperature or preferably at a temperature of from about 700 to 1300C, optionally under pressure, or fabrics or knitted fabrics are successively impregnated with a dyestuff solution, dried and submitted to a brief heat treatment, for example at a temperature of from 1800 to 210'C, in continuous manner.Suitable solvents for the exhaust process are, for example, solvents which are not miscible with water and have a boiling point in the range of from 400 to 170 C, such as aliphatic halogenohydrocarbons, for example methylene chloride, trichioroethane, trichloroethylene, perchloroethylene or trifluorotrichlor- oethane. In particular for a continuous dyeing process solvents which are miscible with water, such as alcohols or dimethylformamide, may be used. The solvents may be present as mixtures and contain further auxiliaries which are soluble in solvents, such as oxalkylation products of fatty alcohols, alkylphenols or fatty acids.
For producing prints on synthetic fiber materials, for example those made from polyesters, polyamides or cellulose triacetate, the dyestuffs may be used in the form of aqueous compositions which may contain, in addition to the finely dispersed dyestuff, suitable thickeners and fixation accelerators. Fixation is generally carried out upon printing and drying by steaming at atmospheric pressure or under elevated pressure upto 2.5 atmosphere gauge for a period of from 10 to 60 minutes or by the action of hot air having a temperature of from 1600 to 210"C for a period of from 30 seconds to 10 minutes.
The dyestuffs according to the invention make it possible to produce on the above-specified fiber materials, with a very good color yield, colorations of high tinctorial strength and good structure. They may
have a range of shades from yellow to blue and they have a high fastness to light, to water, to alkalies, to washing, to perspiration and to thermofixation.
The following Examples illustrate the invention. Parts are by weight.
Example 1:
10.9 Parts of 2-bromo-4-nitroaniline were dissolved in a sufficient quantity of glacial acetic acid. The
resulting solution was introduced into a mixture of 200 parts of water and 20 parts of 33% hydrochloric acid.
The temperature was reduced to 0 to 5 C by the addition of ice. Next, the mixture was diazotized by the
addition of 10ml of 5N sodium nitrite solution. The mixture was stirred for 1 hour, supplemented with 2 parts
of amidosulfonic acid and clarified with kieselguhr. The resulting solution of 14 parts of N-methylsuccinic
acid dimethyl ester-N-ethylaniline in acetic acid, while stirring.Coupling was completed in an acidic medium
at 0 to 5"C. After about 12 hours the resulting dyestuff of the formula
was filtered off, washed until electrolyte-free and dried,
16 Parts of a red dyestuff powder were obtained, suitable for dyeing polyester fibers in aqueous dispersion in clear, red shades having high fastness to light and to sublimation.
Example 2:
7.3 Parts of 2-amino-5-nitrothiazole were dissolved in 30 ml 85% phosphoric acid. Diazotization was carried out at 0 to 5 C by slowly introducing 16 parts of 40% nitrosysulfuric acid. The diazotized mixture was stirred at the specified temperature for 30 minutes. The the excess nitrite was destroyed with 2 parts of amidosulfonic acid.
The resulting diazonium salt solution was allowed to flow slowly into a cooled solution of 13.3 parts
N-methylenesuccinic acid dimethyl ester-N-methylaniline in 50 ml acetone while stirring and cooling. Solid sodium acetate were thereafter added as a buffer.
After stirring for 2 hours the coupling liquor was introduced into 1000 parts of water, the precipitated dyestuff of the formula
was washed until free from electrolyte and dried.
The resulting dyestuff had a very good absorptive power on fiber materials and polyesters, cellulose acetates and polyamides in aqueous dispersion and gave brilliant violet shades of high tinctorial strength and good fastness to light and to sublimation.
Example 3:
By a process analogous to that of Example 1 or Example 2, further dyestuffs according to the invention, having the shade indicated, may be prepared using the components indicated in the following Table:
Example D-NH2 R1 R2 R3 Shade on
No. polyester
(Formula Ill) fibers 3. 4-nitroaniline CH3 CH3 H orange 4. 2-cyano-4-nitroaniline CH3 CH3 H red 5. 2-cyano-4-nitro-6- CH3 CH3 H blueish red
bromoaniline 6. 4-aminobenzoic acid ethyl CH3 CH3 H gold yellow
ester 7. 4-aminoazobenzene CH3 CH3 H orange 8. 4-amino-3-chloro-azobenzene CH3 CH3 H blueish red 9. 2,4,5-trichloroaniline CH3 CH3 H gold-yellow 10. 4-aminoacetanilide CH2 CH3 H gold-yellow 11. 4-cyanoaniline CH3 C2H5 H gold-yellow 12. 2-bromo-4-cyanoaniline CH3 CH3 H orange 13. 2-chloro-4-nitroaniline CH3 CH3 H scarlet 14 4-aminobenzaldoxime CH3 CH3 H reddish yellow 15. 2-cyano-4-nitroaniline CH3 CH3 H blueish red 16. 2,4-dinitroaniline CH3 CH3 H red 17. 2,4-dinitro-6-chloroaniline CH3 CH3 H blueish red 18. 2,6-dichloror-4-nitroaniline CH3 CH3 H ginger 19. 4-aminobenzoic acid ethyl CH3 CH3 H gold-yellow
ester 20. 2-methoxy-4-nitroaniline CH3 CH3 H red 21. 2-amino-5-nitrothiazole CH3 C2H5 H violet 22. 2-amino-6-nitrobenzothiazole CH3 C2H5 H red 23. 2-methyl-4-nitroaniline CH3 C2H5 H red 24. 2,4-dinitro-6-bromoaniline CH3 C2H5 H blueish red 25. 3-amino-5-nitrobenzothiazole CH3 C2H5 H blue 26. 4-nitroaniline CH3 C2H5 CH3 scarlet 27. 2-chloro-4-nitroaniline CH3 C2H5 CH3 red 28. 2-cyano-4-nitroaniline CH3 C2H5 CH3 blueish red 29. 2,4-dinitroaniline CH3 C2H5 CH3 blueish red 30. 2,4-dinitro-5-chloroaniline CH3 C2H5 CH3 violet 31. naphthylamine CH3 C2H5 OCH3 ginger 32. 4-chloro-2-triflurormethyl CH3 C2H5 OCH3 orange
aniline 33. 4-nitro-2-methylsulfonyl CH3 C2H5 OCH3 violet
aniline 34. 2-nitroaniline CH3 C2H5 OCH3 red 35. 3-phenyl-5-amino-1,2,4- CH3 C2H5 OCH3 red
thiadiazole
Claims (18)
1. Awater-insoluble azo dyestuff of the general formula (I)
wherein D represents the radical of a diazo component
of the benzene, azobenzene, naphthalene, thiazole, benzothiazole, thiadiazole, benzisothiazole or indazole series, which is free from sulfonic acid groups and in which the ring or each ring independently is unsubstituted or substituted by one or more substituents selected from halogen atoms and nitro, cyano, alkyl, alkoxy, alklsulfonyl, sulfonamido, trifluoromethyl, alkylcarbonyl, chloroalkylcarbonyl, alkylcarbonylamino, chloroalkylcarbonylamino, benzoyl, chlorobenzoyl, benzoylamino, chlorobenzoylamino, phenoxy, ozime, carboxylic acid alkyl ester and carboxylic acid amide groups, the alkyl and alkoxy groups and moieties each having from 1 to 4 carbon atoms, R1 and R2, which may be the same or different, each represents
an alkyl group having from 1 to 4 carbon atoms, and R3 represents a hydrogen atom or an alkyl or alkoxy group
having from 1 to 4 carbon atoms.
2. A dyestuff as claimed in claim 1, wherein a halogen atom ring substituent is a fluorine, chlorine or bromine atom.
3. The dyestuff of the formula
4. The dyestuff of the formula
5. The dyestuff of the formula
6. The dyestuff of the formula
7. A process for preparing a dyestuff of the general formula (I) given in claim 1, which comprises diazotizing a diazo component of the general formula (II)
D-NH2 (II) wherein D is defined as in claim land coupling the resulting product with a coupling component of the general formula (III)
wherein R1, R2 and R3 are defined as in claim 1, in an acidic or neutral aqueous, aqueous-organic or organic medium.
8. A process as claimed in claim 7, wherein the coupling medium comprises water and/or an organic solvent selected from methanol, ethanol, propanol, butanol, acetone and dimethylformamide.
9. A process as claimed in claim 7 or claim 8, wherein coupling is carried out in the presence of an acid-binding agent.
10. A process as claimed in claim 9, wherein the acid binding agent is pyridine, picoline, triethylamine, sodium, carbonate, potassium carbonate, magnesium oxide or sodium acetate.
11. A process as claimed in claim 7, conducted substantially as described herein.
12. A process as claimed in claim 7, conducted substantially as described in Example 1 or Example 2.
13. A dyestuff as claimed in claim 1, whenever prepared by a process as claimed in any one of claims 7 to 12.
14. A dyeing or printing process wherein a dyestuff as claimed in any one of claims 1 to 6 and 13 is used.
15. A process as claimed in claim 14, wherein a fibrous material of cellulose diacetate, cellulose 21/2 acetate, cellulose triacetate, a polyamide, a polyurethane, a polycarbonate or a linear polyester is dyed or printed.
16. A process as claimed in claim 14, conducted substantially as described herein.
17. A fibrous material of cellulose diacetate, cellulose 21/2 acetate, cellulose triacetate, a polyamide, a polyurethane, a polycarbonate or a linear polyester, wherever dyed or printed with a dyestuff as claimed in any one of claims 1 to 6 and 13.
18. Adyeing or printing preparation which contains a dyestuffas claimed in any one of claims 1 to 6 and 13.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19782825189 DE2825189A1 (en) | 1978-06-08 | 1978-06-08 | NEW, HYDRO-INSOLUBLE AZO DYES, METHODS FOR THEIR MANUFACTURING AND USE FOR COLORING OR PRINTING |
Publications (2)
Publication Number | Publication Date |
---|---|
GB2024235A true GB2024235A (en) | 1980-01-09 |
GB2024235B GB2024235B (en) | 1982-11-10 |
Family
ID=6041364
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB7920036A Expired GB2024235B (en) | 1978-06-08 | 1979-06-08 | Water-insoluble azo dyestuffs process for their manufacture and their use |
Country Status (9)
Country | Link |
---|---|
JP (1) | JPS54161636A (en) |
BE (1) | BE876875A (en) |
CH (1) | CH643579A5 (en) |
DE (1) | DE2825189A1 (en) |
FR (1) | FR2428062A1 (en) |
GB (1) | GB2024235B (en) |
IN (1) | IN150557B (en) |
IT (1) | IT1120787B (en) |
MX (1) | MX148996A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2157305A (en) * | 1984-04-11 | 1985-10-23 | Mitsubishi Chem Ind | Disazo dyestuffs for polyester fibres |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE754634A (en) * | 1969-08-11 | 1971-02-10 | Cassella Farbwerke Mainkur Ag | WATER INSOLUBLE MONOAZOIC COLORANTS AND THEIR PREPARATION |
BE758771A (en) * | 1969-11-11 | 1971-04-16 | Sandoz Sa | AZOIC COMPOUNDS, THEIR PREPARATION AND THEIR USE |
-
1978
- 1978-06-08 DE DE19782825189 patent/DE2825189A1/en not_active Withdrawn
-
1979
- 1979-06-01 IN IN572/CAL/79A patent/IN150557B/en unknown
- 1979-06-05 CH CH523879A patent/CH643579A5/en not_active IP Right Cessation
- 1979-06-06 JP JP7001479A patent/JPS54161636A/en active Pending
- 1979-06-06 IT IT23330/79A patent/IT1120787B/en active
- 1979-06-07 MX MX177968A patent/MX148996A/en unknown
- 1979-06-08 BE BE0/195656A patent/BE876875A/en not_active IP Right Cessation
- 1979-06-08 FR FR7914694A patent/FR2428062A1/en active Granted
- 1979-06-08 GB GB7920036A patent/GB2024235B/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2157305A (en) * | 1984-04-11 | 1985-10-23 | Mitsubishi Chem Ind | Disazo dyestuffs for polyester fibres |
Also Published As
Publication number | Publication date |
---|---|
GB2024235B (en) | 1982-11-10 |
IT7923330A0 (en) | 1979-06-06 |
JPS54161636A (en) | 1979-12-21 |
FR2428062B1 (en) | 1984-03-30 |
MX148996A (en) | 1983-08-05 |
IT1120787B (en) | 1986-03-26 |
IN150557B (en) | 1982-11-13 |
DE2825189A1 (en) | 1979-12-13 |
CH643579A5 (en) | 1984-06-15 |
BE876875A (en) | 1979-12-10 |
FR2428062A1 (en) | 1980-01-04 |
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