CH487977A - Process for the production of disazo and polyazo dyes - Google Patents
Process for the production of disazo and polyazo dyesInfo
- Publication number
- CH487977A CH487977A CH258965A CH258965A CH487977A CH 487977 A CH487977 A CH 487977A CH 258965 A CH258965 A CH 258965A CH 258965 A CH258965 A CH 258965A CH 487977 A CH487977 A CH 487977A
- Authority
- CH
- Switzerland
- Prior art keywords
- dyes
- amino
- acid
- amino group
- hydroxynaphthalene
- Prior art date
Links
- 239000000975 dye Substances 0.000 title claims description 26
- -1 polyazo Polymers 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 10
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 6
- 238000010168 coupling process Methods 0.000 claims description 6
- 238000005859 coupling reaction Methods 0.000 claims description 6
- 150000001555 benzenes Chemical class 0.000 claims description 4
- SXCSXKQTOUHQIY-UHFFFAOYSA-N 4-hydroxynaphthalene-1,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(O)=CC=C(S(O)(=O)=O)C2=C1 SXCSXKQTOUHQIY-UHFFFAOYSA-N 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
- 230000003381 solubilizing effect Effects 0.000 claims description 2
- 230000009918 complex formation Effects 0.000 claims 1
- 150000004696 coordination complex Chemical class 0.000 claims 1
- 239000002253 acid Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000004627 regenerated cellulose Substances 0.000 description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 229950011260 betanaphthol Drugs 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- ZYDILTJZICMURJ-UHFFFAOYSA-N 1-(2,3-diaminophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(N)=C1N ZYDILTJZICMURJ-UHFFFAOYSA-N 0.000 description 1
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 1
- ZARYBZGMUVAJMK-UHFFFAOYSA-N 2-amino-4-chloro-5-nitrophenol Chemical compound NC1=CC(Cl)=C([N+]([O-])=O)C=C1O ZARYBZGMUVAJMK-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
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- DTFKRVXLBCAIOZ-UHFFFAOYSA-N 2-methylanisole Chemical compound COC1=CC=CC=C1C DTFKRVXLBCAIOZ-UHFFFAOYSA-N 0.000 description 1
- ZAHMVJOIEBCBPB-UHFFFAOYSA-N 3-(3-methyl-5-oxo-4h-pyrazol-1-yl)benzoic acid Chemical compound O=C1CC(C)=NN1C1=CC=CC(C(O)=O)=C1 ZAHMVJOIEBCBPB-UHFFFAOYSA-N 0.000 description 1
- RHPXYZMDLOJTFF-UHFFFAOYSA-N 3-amino-4-hydroxy-5-nitrobenzenesulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC([N+]([O-])=O)=C1O RHPXYZMDLOJTFF-UHFFFAOYSA-N 0.000 description 1
- USWINTIHFQKJTR-UHFFFAOYSA-N 3-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(O)=CC2=C1 USWINTIHFQKJTR-UHFFFAOYSA-N 0.000 description 1
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 1
- WHSXTWFYRGOBGO-UHFFFAOYSA-N 3-methylsalicylic acid Chemical compound CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 description 1
- AFPHTEQTJZKQAQ-UHFFFAOYSA-N 3-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1 AFPHTEQTJZKQAQ-UHFFFAOYSA-N 0.000 description 1
- BBEWSMNRCUXQRF-UHFFFAOYSA-N 4-methyl-3-nitrobenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1[N+]([O-])=O BBEWSMNRCUXQRF-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
- OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 description 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
- RUCHWTKMOWXHLU-UHFFFAOYSA-N 5-nitroanthranilic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(O)=O RUCHWTKMOWXHLU-UHFFFAOYSA-N 0.000 description 1
- TWLMSPNQBKSXOP-UHFFFAOYSA-N 6358-09-4 Chemical compound NC1=CC([N+]([O-])=O)=CC(Cl)=C1O TWLMSPNQBKSXOP-UHFFFAOYSA-N 0.000 description 1
- ZLHGMJOGMLVDFS-UHFFFAOYSA-N 7-benzamido-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C=1C=C2C(O)=CC(S(O)(=O)=O)=CC2=CC=1NC(=O)C1=CC=CC=C1 ZLHGMJOGMLVDFS-UHFFFAOYSA-N 0.000 description 1
- HMNPDEGBVWDHAR-UHFFFAOYSA-N 8-aminonaphthalen-1-ol Chemical compound C1=CC(O)=C2C(N)=CC=CC2=C1 HMNPDEGBVWDHAR-UHFFFAOYSA-N 0.000 description 1
- KMXMLAGYNHELHA-UHFFFAOYSA-N 8-hydroxynaphthalene-1,3,6-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 KMXMLAGYNHELHA-UHFFFAOYSA-N 0.000 description 1
- DQIVFTJHYKDOMZ-UHFFFAOYSA-N 96-67-3 Chemical compound NC1=CC([N+]([O-])=O)=CC(S(O)(=O)=O)=C1O DQIVFTJHYKDOMZ-UHFFFAOYSA-N 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- POJOORKDYOPQLS-UHFFFAOYSA-L barium(2+) 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O POJOORKDYOPQLS-UHFFFAOYSA-L 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- HLVXFWDLRHCZEI-UHFFFAOYSA-N chromotropic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 HLVXFWDLRHCZEI-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 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 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000002268 wool Anatomy 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
- 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
- C09B31/025—Disazo dyes containing acid groups, e.g. -COOH, -SO3H, -PO3H2, -OSO3H, -OPO2H2; Salts thereof
-
- 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
- C09B31/16—Trisazo 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/38—Trisazo dyes ot the type
-
- 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/24—Disazo or polyazo compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung von Dis- und Polyazofarbstoffen Gegenstand der Erfindung ist ein Verfahren zur Herstellung von Dis- und Polyazofarbstoffen, welches darin besteht, dass man 1 Mol einer Verbindung der Formel
EMI0001.0006
worin A einen ein- oder zweikernigen aromatischen Rest und R eine primäre oder sekundäre Amirlogruppe bedeuten, mit 1 Mol eines Carbonsäurechlorids der Benzolreihe,
welches einen durch Reduktion in eine Aminogruppe überführbaren Substituenten enthält, kondensiert, diesen Substituenten durch Reduktion in die Aminogruppe überführt, diese weiterdiazotiert und mit einer beliebigen Kupplungskomponente kuppelt und die zum Aufbau der Farbstoffe zu verwendenden einzelnen Komponenten so wählt, dass diese zumindest die für die Wasserlöslichkeit der Farbstoffe notwendige Anzahl löslichmachender Gruppen enthalten.
Die Kom ponenten können in ortho-Stellung zu dem mit 1- Hydroxynaphtiialin-4,6-disulfonsäure verknüpften Azobrücken einen zur Metallkomplexbildung befähig ten Substituenten enthalten. Die erhaltenen Farbstoffe können in Substanz mit kupfer- oder nickelabgebenden Mitteln behandelt werden.
Verbindungen der Formel (I), in denen R eine pri märe Aminogruppe bedeutet, lassen sich durch Reduk tion der nachstehend beschriebenen Nitroverbindun gen, z. B. mittels<B>Alk</B> alimetallsttlfiden, in alkalischem Milieu herstellen oder durch Verseifung eines AcyIderi- vats der Aminoazofarbstoffe der Formel (I).
Verbindungen der Formel (1), in denen R eine Nitrogruppe bedeutet, können beispielsweise so aufge baut werden, dass man z. B. eine 1-Amino-4-nitroben- zol-2-carbonsäure diazotiert und hierauf in alkalischem Medium mit der 1-HydroxynaphthaIin-4,6-disulfon- säure kuppelt.
Anstelle der 1-Amino-4-nitrobenzoI- 2-carbonsäure können auch Verbindungen wie 1-Amino-4-(oder-5-)-nitro-2-hydroxybenzol, 1-Amino-2-methoxy-4-(oder-5-)-nitrobenzol, 1-Amino-2-carboxy-methoxy-4-(oder- -5-)-nitrobenzol, 1-Hydroxy-2-amino-4-chlor-5-nitrobenzol, 1-Hydroxy-6-amino-2-chlor-4-nitrobenzol, 1-Hydroxy-2-amino-4-nitrobenzol-6-sulfonsäure, 1-Hydroxy-2-amino-6-nitrobenzol-4-suIfonsäure, 1-(4'-Nitrobenzoyl-)
-amino-4-aminobenzol- 3-carbonsäure verwendet werden. Diese Aminoazofarbstoffe können durch Alkylie- rung, z. B. mit Dimethylsulfat oder 4-Methylbenzol- 1-sulfonsäuremethylester oder mit Äthylenoxyd bzw. Athylenchlorhydrin usw. in sekundäre Aminoderivate übergeführt werden.
Die Aminoazofarbstoffe der Formel (1) können mit einem Monocarbonsäurechlorid der Benzolreihe, wel ches einen in eine Aminogruppe überführbaren Substi- tuenten enthält, kondensiert werden. Als solche Säure chloride kommen in Betracht z.
B. die Chloride der 4-Nitrobenzoesäure, T-Nitro-3-methylbenzoesäure, 3-Nitro-4-methylbenzoesäure> oder 3-Nitrobenzoe- säure. Die erhaltenen Kondensationsprodukte werden hierauf mit Reduktionsmitteln, wie Alkalimetallsulfi- den, in alkalischem Milieu bei erhöhter Temperatur zum Am inoderivat reduziert. Letztere werden diazo- tiert und auf eine Schlusskomponente gekuppelt. Als Schlusskomponente kommen z.
B. in Frage Salicyl- säure Kresotinsäure# 1- oder -2-Hydroxy-Naphthalin und deren Mono-, Di- und Trisulfonsäuren, wie 1- I-Iydroxynaphthalin-3-(oder -4-)sulfonsäure, 2-Hydro- xynaphthalin-4-(6- oder -7-)sulfonsätire, 1-Hydroxy- naphthalin-4,6-(3,6-, -4,8- oder -3,8-)-disulfonsäure, 2-Hydroxynaphthalin-3,6-disulfonsäure,
1-Hydroxynaphthalin-3,6,8-trisulfonsäure, 1,8-Dihydroxynaphthalin-3,6-disulfonsäure, Pyrazolone und deren \Substitutionaprodtrl.te wir, 1-Phenyl-3-methyl-5-pyrazolon, 1-Phenyl-3-methyl-5-pyrazolon-3'-sulfonsäure oder -4'-sulfonsäure oder -3',5'-disulfonsäure oder ' -2',4'- oder -2',5'-disulfonsäure oder 1-Phenyl-5=pyrazolon=3-carbonsäure oder 1-(3'-Carboxyphenyl)-3-methyl-5-pyrazolon usw.
sowie Amino-hydroxynaphthalinmono- und disulfonsäuren und deren Acetylamino- und Arylaminoderivate, z. B. 2-Amino-5-hyydroxynaphthalin-7-sulfonsäure, deren Acetyl-, Benzoyl-, Phenyl-, Anisidyl-, Chloracetyl-, Crotonyl- oder Harnstoffderivate, 1-Amino-8-hydrtrx5,- naphthalin-4-sulfonsäure, deren Acetyl-,
Benzoyl- oder Phenylderivate, 1-Amino-8-hydroxvnaphthälin='3,6- oder -2,4-disulfonsäure, 2-Amino-5-hydroxynaphtha- lin-7-sulfonsäure, 2-Amino-8-h.ydroxyn4phthalin-6-sul- fonsäure -arrä deren Aoetyl-, $enzuyl- -trnd @PhenyIderi- vate, AcetoacetylaminobenzoI,
1-Acetoacetylamino-2-, -3- oder -4-methyl-, -:mefhoxy- -oder ,=clrlocbenztil tmd deren Sulfonsäuren sowie Barbitursäure.
Andere Schlusskomponenten sind z. B. Monoazo- farbstoffe mit einer kupplungsfähigen Stelle, wie
EMI0002.0057
Anstelle einer Schlusskomponente kommen auch Mittelkomponenten, wie Aminobenzol, 3-Amino-l-methylbenzol, 3-Amino-4-,methoxy-'1-methylbenzol, 3-Amino-1,4-dimethylbenzol, 3 Amino-l-acetyl-aminobenzol, 3-Amino-l-sulfoacetylaminobenzol, 1-Aminonaphthalin, 1-Aminonaphthalin-6- oder -7-sulfonsäure in Frage.
Die entstandenen Knpplungsgrodukte können hierauf in üblicher Weise weiterdiazotiert und mit einer beliebigen Schlusskomponente wie z. B. die oben er wähnten, vorzugsweise in Gegenwart von Pyridin oder Dimethylformamid, gekuppelt und die erhaltenen Farb stoffe können, wenn sie metallisierbare Gruppen ent halten, anschliessend in Substanz in die Metallkom- plexverbindungen übergeführt werden.
Die Behandlung mit kupfer- oder nickelabgebenden Verbindungen kann in Substanz in sehr verschiedener Art ausgeführt wer den, z. B. durch Erhitzen der Farbstofflösungen mit wasserlöslichen Kupfer- oder Nickelsalzen in schwach saurem bis schwach alkalischem Medium, vorzugsweise in Gegenwart von Ammoniak oder organischen Basen, wie Pyridin, Mono- -oder Dia'thanolamin, Methylamin, Di- und Trimethylamin, Propylamin usw.,
oder in der konzentrierten wässrigen Lösung von Alkalimetallsal- zen aliphatischer Monocarbonsäuren, wie z. B. Natriu- macetat. Die nach dem Verfahren erhältlichen neuen Farbstoffe dienen .zum Färben, Klötzen oder Bedruk- ken von Baumwolle und Fasern aus regenerierter Cel- lulose in sehr echten, je nach dem Aufbau variierenden Farbtönen.
Insbesondere erhält man sehr lichtechte blaue, braune und rote Färbungen. Durch gleichzeitige oder nachträgliche Behandlung der Färbungen mit Polyalkylenpolyaminen können die Nassechtheiten noch verbessert werden.
Die Färbungen :auf natürlicher und regerterierter Cellulose besitzen sehr gute Lichtechtheit und Nass- echtheiten wie Wasch-, Wasser-, Schweiss-, Seewas- ser-, Nassbügelechtheit, Wassertropfenechtheit usw. Zudem besitzen sie gute Avivierechtheit, Formalde hyd-, Alkali- und Säureechtheit.
Die neuen Farbstoffe reservieren sehr gut Celluloseacetat, Wolle, Seide, Nylon, Perlon, Acryl- und Polyesterfasern. Dit; riasfu- meechtheit'ist ausgezeichnet.
In den -nachfolgenden Beispielen bedeuten die Teile Gewichtsteile und die Prozente Gewichtsprozente. 'Die Temperaturen sind in Celsiusgraden angegeben. <I>Beispiel 1</I> 55,6 Teile des Aminomonoazofarbstoffes, den man durch Kuppeln der Diazoverbindung von 1-Amino- 4-nitrobenzol mit der 1-Hydroxy-naphthalin-4,6-disul- fonsäure,
anschliessende Reduktion der Nitrogruppe zur Aminogruppe und Kondensation dieses Aminoazo- farbstoffs mit 4-Nitrobenzoylchlorid und nochmalige Reduktion der Nitrogruppe zur Aminogruppe erhält, werden in 1200 Teilen Wasser gelöst, mit 7 Teilen Natriumnitrit versetzt und unter sehr gutem Rühren durch Einstürzen von 30 Teilen 30 o/oiger Salzsäure bei 10-15 dianotiert.
Sobald die Diantierung fertig ist, wird die ausgeschiedene 'braunrote Diazoverbindung unter Rühren in eine auf f0-15 gekühlte Vorlage von 34,3 Teilen 1-Hydroxy-6-benzoylamino-naphthälin- 3-sulfonsäure, 500 Teilen Wasser und 35 Teilen Natri- umhydrogencarbonat eingetragen. 'Die 'Kupplung er folgt sehr rasch.
Der entstandene blaustichig rote Farb- stöff wird durch .Aussahen wie üblich isoliert, durch Urrilösen gereinigt und bei 90-95 im Vakuum ge trocknet.
Der neue Farbstoff, ein dunkles rotes Pulver, lbst sich in Wasser mit klar roter Farbe und färbt Baum wolle und Fasern aus regenerierter Cellulose in sehr brillanten roten Tönen von ausgezeichneten Echtheits eigenschaften.
In der nachfolgenden Tabelle sind weitere Disazo- bzw. Polyazofarbstoffe aufgeführt, welche auf ähnliche Weise nach den Artgaben des Beispiels 1 hergestellt werden können. Sie entsprechen in der metallfreien Form der Formel
EMI0003.0114
worin A3 einen gegebenenfalls substituierten Rest der Benzol-, Stilben- oder Diphenylreihe, B einen gegebe nenfalls substituiertest Rest der Benzolreihe, K, den Rest einer Kupplungskomponente,
welche selbst -schon Azogruppen enthalten kann, und R, Wasserstoff oder gegebenenfa7is substituiertes Alkyl bedeuten.
EMI0004.0001
EMI0005.0001
Zum Färben verfährt man wie folgt: Man löst 0,1 Teile des im Beispiel 1 erhaltenen Disazofarbstoffs in 300 Teilen kalkfreiem Wasser. In dieser Flotte färbt man 10 Teile angehetztes Baum wolltuch, indem man das Bad, beginnend bei einer Temperatur von 30 , innerhalb von 30 Minuten auf 100 erhitzt und während 15 Minuten bei dieser Tem peratur hält.
Im Verlauf des Färbeprozesses gibt man dem Bad portionenweise 3-4 Teile Natriumsulfat in Form einer 10 oloigen wässrigen Lösung zu. Hierauf lässt man das Färbegut in der Flotte innerhalb von 15-20 Minuten auf 50 abkühlen,, nimmt es heraus, spült es mit Wasser, schwingt es aus und trocknet es. Durch Nachbehandeln des Färbegutes mit einer basi schen, kationaktiven Kupferkomplexverbindung wer den die Echtheitseigenschaften der Färbung deutlich verbessert.
Process for the preparation of disazo and polyazo dyes The invention relates to a process for the preparation of disazo and polyazo dyes, which consists in adding 1 mol of a compound of the formula
EMI0001.0006
wherein A is a mono- or binuclear aromatic radical and R is a primary or secondary amirlo group, with 1 mol of a carboxylic acid chloride of the benzene series,
which contains a substituent which can be converted into an amino group by reduction, condenses, converts this substituent into the amino group by reduction, further diazotizes it and couples it with any coupling component and selects the individual components to be used to build up the dyes so that they are at least those for water solubility of the dyes contain the necessary number of solubilizing groups.
The components can contain a substituent capable of forming metal complexes in the ortho position to the azo bridges linked with 1-hydroxynaphthiialine-4,6-disulfonic acid. The dyes obtained can be treated as they are with copper- or nickel-releasing agents.
Compounds of the formula (I) in which R is a primary amino group can be obtained by reducing the nitro compounds described below, eg. B. by means of <B> Alk </B> alimetallsttlfiden, in an alkaline medium or by saponification of an acyl derivative of the aminoazo dyes of the formula (I).
Compounds of the formula (1) in which R is a nitro group can be built up, for example, that one z. B. a 1-amino-4-nitrobenzene-2-carboxylic acid is diazotized and then coupled with the 1-hydroxynaphthalene-4,6-disulfonic acid in an alkaline medium.
Instead of 1-amino-4-nitrobenzoI-2-carboxylic acid, compounds such as 1-amino-4- (or-5 -) - nitro-2-hydroxybenzene, 1-amino-2-methoxy-4- (or-5 -) - nitrobenzene, 1-amino-2-carboxy-methoxy-4- (or- -5 -) - nitrobenzene, 1-hydroxy-2-amino-4-chloro-5-nitrobenzene, 1-hydroxy-6-amino -2-chloro-4-nitrobenzene, 1-hydroxy-2-amino-4-nitrobenzene-6-sulfonic acid, 1-hydroxy-2-amino-6-nitrobenzene-4-sulfonic acid, 1- (4'-nitrobenzoyl-)
-amino-4-aminobenzene-3-carboxylic acid can be used. These aminoazo dyes can be obtained by alkylation, e.g. B. with dimethyl sulfate or 4-methylbenzene-1-sulfonic acid methyl ester or with ethylene oxide or ethylene chlorohydrin, etc. are converted into secondary amino derivatives.
The aminoazo dyes of the formula (1) can be condensed with a monocarboxylic acid chloride of the benzene series which contains a substituent which can be converted into an amino group. Such acid chlorides are suitable for.
B. the chlorides of 4-nitrobenzoic acid, T-nitro-3-methylbenzoic acid, 3-nitro-4-methylbenzoic acid> or 3-nitrobenzoic acid. The condensation products obtained are then reduced to the amine derivative using reducing agents such as alkali metal sulfides in an alkaline medium at elevated temperature. The latter are diazoated and coupled to a final component. As a final component come z.
B. in question salicylic acid cresotinic acid # 1- or -2-hydroxy-naphthalene and their mono-, di- and trisulfonic acids, such as 1- I-hydroxynaphthalene-3- (or -4-) sulfonic acid, 2-hydroxynaphthalene -4- (6- or -7-) sulfonic acid, 1-hydroxynaphthalene-4,6- (3,6-, -4,8- or -3,8-) disulfonic acid, 2-hydroxynaphthalene-3, 6-disulfonic acid,
1-Hydroxynaphthalene-3,6,8-trisulfonic acid, 1,8-dihydroxynaphthalene-3,6-disulfonic acid, pyrazolones and their substitution methods, 1-phenyl-3-methyl-5-pyrazolone, 1-phenyl-3 -methyl-5-pyrazolone-3'-sulfonic acid or -4'-sulfonic acid or -3 ', 5'-disulfonic acid or' -2 ', 4'- or -2', 5'-disulfonic acid or 1-phenyl-5 = pyrazolone = 3-carboxylic acid or 1- (3'-carboxyphenyl) -3-methyl-5-pyrazolone etc.
and also amino-hydroxynaphthalene mono- and disulfonic acids and their acetylamino and arylamino derivatives, e.g. B. 2-Amino-5-hydroxynaphthalene-7-sulfonic acid, its acetyl, benzoyl, phenyl, anisidyl, chloroacetyl, crotonyl or urea derivatives, 1-amino-8-hydrtrx5, - naphthalene-4-sulfonic acid, their acetyl,
Benzoyl or phenyl derivatives, 1-amino-8-hydroxynaphthalene = 3,6- or -2,4-disulfonic acid, 2-amino-5-hydroxynaphthalin-7-sulfonic acid, 2-amino-8-hydroxyn-phthaline- 6-sulphonic acid -arra whose aoetyl-, $ enzuyl- trnd @ phenyl derivatives, acetoacetylaminobenzoI,
1-acetoacetylamino-2-, -3- or -4-methyl-, -: mefhoxy- or, = clrlocbenztil and their sulfonic acids and barbituric acid.
Other final components are e.g. B. Monoazo dyes with a coupling point, such as
EMI0002.0057
Instead of a final component there are also middle components such as aminobenzene, 3-amino-1-methylbenzene, 3-amino-4-, methoxy-1-methylbenzene, 3-amino-1,4-dimethylbenzene, 3-amino-1-acetyl-aminobenzene , 3-Amino-1-sulfoacetylaminobenzene, 1-aminonaphthalene, 1-aminonaphthalene-6- or -7-sulfonic acid are possible.
The resulting Knpplungsgrodukte can then further diazotized in the usual way and with any final component such. B. those mentioned above, preferably in the presence of pyridine or dimethylformamide, coupled and the resulting dyes can, if they contain metallizable groups, then be converted in substance into the metal complex compounds.
The treatment with copper or nickel releasing compounds can be carried out in substance in very different ways who the, z. B. by heating the dye solutions with water-soluble copper or nickel salts in a weakly acidic to weakly alkaline medium, preferably in the presence of ammonia or organic bases such as pyridine, mono- or dia'thanolamine, methylamine, di- and trimethylamine, propylamine, etc. ,
or in the concentrated aqueous solution of alkali metal salts of aliphatic monocarboxylic acids, such as. B. sodium acetate. The new dyes obtainable according to the process are used to dye, block or print cotton and fibers made from regenerated cellulose in very real color shades that vary depending on the structure.
In particular, very lightfast blue, brown and red colorations are obtained. The wet fastness properties can be further improved by simultaneous or subsequent treatment of the dyeings with polyalkylene polyamines.
The dyeings: on natural and regenerated cellulose have very good fastness to light and wet fastness such as fastness to washing, water, perspiration, sea water, wet ironing, fastness to water drops, etc. In addition, they have good fastness to release, formaldehyde, alkali and acid fastness .
The new dyes reserve very well cellulose acetate, wool, silk, nylon, perlon, acrylic and polyester fibers. Diet; riasfume authenticity is excellent.
In the examples below, the parts are parts by weight and the percentages are percentages by weight. The temperatures are given in degrees Celsius. <I> Example 1 </I> 55.6 parts of the amino monoazo dye, which is obtained by coupling the diazo compound of 1-amino-4-nitrobenzene with 1-hydroxynaphthalene-4,6-disulfonic acid,
Subsequent reduction of the nitro group to the amino group and condensation of this aminoazo dye with 4-nitrobenzoyl chloride and repeated reduction of the nitro group to the amino group are dissolved in 1200 parts of water, 7 parts of sodium nitrite are added and 30 parts of 30% are collapsed with very good stirring. oiger hydrochloric acid dianotized at 10-15.
As soon as the diantation is complete, the precipitated brown-red diazo compound is poured into a receiver, cooled to f0-15, of 34.3 parts of 1-hydroxy-6-benzoylamino-naphthalene-3-sulfonic acid, 500 parts of water and 35 parts of sodium hydrogen carbonate, while stirring registered. 'The' coupling takes place very quickly.
The resulting bluish red dye is isolated by .Aussahen as usual, cleaned by loosening and dried at 90-95 in a vacuum.
The new dye, a dark red powder, dissolves in water with a clear red color and dyes cotton and fibers from regenerated cellulose in very brilliant red shades with excellent fastness properties.
The table below lists further disazo and polyazo dyes which can be prepared in a similar manner according to the instructions in Example 1. In the metal-free form, they correspond to the formula
EMI0003.0114
wherein A3 is an optionally substituted radical of the benzene, stilbene or diphenyl series, B an optionally substituted radical of the benzene series, K, the remainder of a coupling component,
which itself may already contain azo groups, and R, hydrogen or optionally substituted alkyl.
EMI0004.0001
EMI0005.0001
The procedure for dyeing is as follows: 0.1 part of the disazo dye obtained in Example 1 is dissolved in 300 parts of lime-free water. In this liquor, 10 parts of attached cotton cloth are dyed by heating the bath to 100 within 30 minutes, starting at a temperature of 30, and keeping it at this temperature for 15 minutes.
During the dyeing process, 3-4 parts of sodium sulphate in the form of a 10% aqueous solution are added to the bath in portions. The dyed material is then allowed to cool to 50 in the liquor within 15-20 minutes, it is removed, rinsed with water, swung out and dried. By treating the material to be dyed with a basic, cation-active copper complex compound, the fastness properties of the dye are significantly improved.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH258965A CH487977A (en) | 1960-04-08 | 1960-04-08 | Process for the production of disazo and polyazo dyes |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH398660A CH400417A (en) | 1960-04-08 | 1960-04-08 | Process for the preparation of disazo dyes |
| CH258965A CH487977A (en) | 1960-04-08 | 1960-04-08 | Process for the production of disazo and polyazo dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH487977A true CH487977A (en) | 1970-03-31 |
Family
ID=25690856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH258965A CH487977A (en) | 1960-04-08 | 1960-04-08 | Process for the production of disazo and polyazo dyes |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH487977A (en) |
-
1960
- 1960-04-08 CH CH258965A patent/CH487977A/en not_active IP Right Cessation
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