CH487978A - Process for the production of disazo and polyazo dyes - Google Patents
Process for the production of disazo and polyazo dyesInfo
- Publication number
- CH487978A CH487978A CH259065A CH259065A CH487978A CH 487978 A CH487978 A CH 487978A CH 259065 A CH259065 A CH 259065A CH 259065 A CH259065 A CH 259065A CH 487978 A CH487978 A CH 487978A
- Authority
- CH
- Switzerland
- Prior art keywords
- dyes
- parts
- coupling
- production
- contain
- Prior art date
Links
- 239000000975 dye Substances 0.000 title claims description 19
- -1 polyazo Polymers 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 11
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title description 4
- 230000008878 coupling Effects 0.000 claims description 11
- 238000010168 coupling process Methods 0.000 claims description 11
- 238000005859 coupling reaction Methods 0.000 claims description 11
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000000126 substance Substances 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
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 230000003381 solubilizing effect Effects 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims 1
- 230000009918 complex formation Effects 0.000 claims 1
- 150000004696 coordination complex Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 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
- 150000004985 diamines Chemical class 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000004627 regenerated cellulose Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-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
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-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
- 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
- LRDIEHDJWYRVPT-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 LRDIEHDJWYRVPT-UHFFFAOYSA-N 0.000 description 1
- IMZSHPUSPMOODC-UHFFFAOYSA-N 5-oxo-1-phenyl-4h-pyrazole-3-carboxylic acid Chemical compound O=C1CC(C(=O)O)=NN1C1=CC=CC=C1 IMZSHPUSPMOODC-UHFFFAOYSA-N 0.000 description 1
- HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 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
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal 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
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 229910052742 iron Inorganic materials 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
- 150000002815 nickel 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
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-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
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 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
- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo 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
- C09B35/36—Trisazo dyes of 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
- 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 zurHerstellung von Dis- und Polyazofarbstoffen Gegenstand der Erfindung ist ein Verfahren zur Herstellung von Dis.- und Polyazofarbstoffen, welches darin besteht, dass man Verbindungen der Formel
EMI0001.0008
worin A einen ein- oder zweikernigen aromatischen Rest und R.
eine Diazoniumgruppe bedeuten, 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 An zahl löslichmachender Gruppen enthalten.
Die Kompo nenten können in ortho-Stellung zu den mit 1-Hydro- xynaphthalin-4,6-disulfonsäure verknüpften Azobrük- ken einen zur MetallkompIexbildung befähigten Substi- tuenten. enthalten. Die erhaltenen Farbstoffe können in Substanz mit kupfer- oder nickelabgebenden Mitteln behandelt werden.
Verbindungen der Formel (I), in denen R den Rest einer Diazoniumgruppe bedeutet, können aus den ent sprechenden Aminofarbstoffen durch Diazotieren her gestellt und anschliessend mit einer Kupplungskompo nente vereinigt werden, wobei man eine Mittelkompo nente verwenden kann; die so erhaltenen Kupplungs produkte können weiterdiazotiert und mit einer Schlusskomponente gekuppelt werden.
Als Mittelkomponenten kommen in Betracht: Aminobenzol, 3-Amino-l-msthylbenzol, 3-Amino-4-methoxy-l-methylbenzol, 3-Amino-1,4-dimethylbenzol, 3-Amino-l-acetyl-aminobenzo@ 3-Amino-l-sulfoacetylaminubenzol, 1-Aminonaphthalin\,. 1-Aminonaphthalin-6- oder -7-sulfonsäure, 1-Amino-2-methoxy- oder -2-äthoxynaphthalin-6-sulfonsäure. Als Schlusskomponenten kommen z.
B. in Frage Salicylsäure, Kresotinsäure, 1- oder -2-Hydroxy-Naph- thaEn und' deren Mono-, Di- und Trisulfonsäuren, wie 1-Hydroxynaphthalin-3-(oder -4-)-sulfonsäure,. 2- Hydroxynaphthalin-4-(6- oder -7 )-sulfonsäure, 1- Hydroxynaphthalirn4,6-(3,6-,. 4,8- oder -3,8-)=disulfon- säure;
2-Hydroxynaphthalin-3,6-disulfonsäure, 1- Hydroxynaphthalin-3,6;8-trisulfonsäure, 1,8-Dihydro- xynaphthalin-3,6-disulfonsättre, Pyrazolone und deren Substitutionsprodukte wie 1-PhenyI-3-methyl-5-pyrazo- Ion, 1-Phenyl-3-methyl,5-pyrazolon-3"-suIfonsäure oder -4:
-sulfonsäure oder -<B>Y</B>,. 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-hydroxynaph- thalinmono- und -disulfonsäuren und deren Acetyl- anüno- und Arylaminoderivate, z:.
B. 2r.Amino-5-hydro- xynaphthalin 7-sulfonsäure, deren. Acetyl-, Berrzoyl=, Phenyl-; Anisidyl-,. Chloracetyl-, Crotonyl- oder Harn stoffderivate,.
1-Amino-8-hydroxy-naphthalin-4-sulfon- säure, deren Acetyl-, Benzoyl- oder Phenylderivate, 1-Amino-8-hydroxy-naphthalin-3,6- oder -2,4-disulfon- säure, 2-Amino-5-hydroxy-naphthalin-7-sulfonsäure, 2-Amino-8-hydroxynaphthalin-6-sulfonsäure und deren Acetyl-, Benzoyl- und Phenylderivate, Acetoacetylami- nobenzol,
1-Acetoacetylamino-2-, -3- oder -4-methyl-, -methoxy- oder -chlorbenzol und deren Sulfonsäuren sowie Barbitursäure.
Andere Schlusskomponenten sind, z. B. Monoazo- farbstoffe mit. einer kupplungsfähigen Stelle, wie
EMI0002.0001
Azine wie
EMI0002.0004
Anstelle einer Schlusskomponente kommen auch Mittelkomponenten in Betracht.
Die erhaltenen Kupplungsprodukte aus einer Ver bindung der Formel (I) und einer Mittelkomponente können in üblicher Weise weiterdiazotiert und mit einer beliebigen Schlusskomponente wie z. B. die oben erwähnten, vorzugsweise in Gegenwart von Pyridin oder Dimethylformamid, gekuppelt und die erhaltenen Farbstoffe können, wenn sie metallisierbare Gruppen enthalten, in Substanz in die Metallkomplexverbindung übergeführt werden.
Die Diazoazoverbindung der Formel (I) kann man beispielsweise so gewinnen, dass man 1 Mol eines Dia min tetrazotiert und mit 1 Mol der 1-Hydroxy-naph- tlialin-4,6-disulfonsäure einseitig kuppelt.
Als solche Diamine kommen vor allem in Betracht: 4,4'-Diamino- 3,3'-dimethoxy-l,l'-diphenyl, 4,4'-Dianiino-3,3'- dicarboxy-1,1'-diphenyl, 4,4'-Diamino-3,3'-dicarboxy- methoxy-1,1-diphenyl, 4,4'-Diamino-3,3'-dihydroxy- 1,1'-diphenyl. Diese Diazoniumverbindungen können, in gleicher Weise wie oben beschrieben,
mit einer Mit telkomponente vereinigt werden und dann weiterdiazo- tiert und mit einer Schlusskomponente vereinigt oder direkt mit einer der oben angeführten Schlusskompo- nenten vereinigt werden, worauf die erhaltenen Farb stoffe, wenn sie metallisierbare Gruppen enthalten, in Substanz metallisiert werden.
Die Behandlung mit kupfer- oder nickelabgebenden Verbindungen kann in Substanz in sehr verschiedener Art ausgeführt werden, z. B. durch Erhitzen der Farb- stofflösungen mit wasserlöslichen Kupfer- oder Nickel salzen in schwach saurem bis schwach alkalischem Medium, vorzugsweise in Gegenwart von Ammoniak oder organischen Basen, wie Pyridin, Mono- oder Diäthanolamin, Methylamin, Di- und Trimethylamin, Propylamin usw.,
oder in der konzentrierten wässrigen Lösung von Alkalimetallsalzen aliphatischer Monocar- bonsäuren, wie z. B. Natriumacetat. Die nach dem Verfahren erhältlichen neuen Farbstoffe dienen zum Färben, Klotzen oder Bedrucken von Baumwolle und Fasern aus regenerierter Cellulose in sehr echten, je nach dem Aufbau variierenden Farbtönen. Insbeson dere erhält man sehr lichtecht blaue, graue, grüne, braune und rote Färbungen.
Durch gleichzeitige oder nachträgliche Behandlung der Färbungen mit Polyalky- lenpolyaminen können die Nassechtheiten noch verbes sert werden.
Die Färbungen auf natürlicher und regenerierter Cellulose besitzen sehr gute Lichtechtheit und 1"Tass- 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. Die Gasfu- meechtheit ist ausgezeichnet.
In den nachfolgenden Beispielen bedeuten die Teile Gewichtsteile und die Prozente Gewichtsprozente. Die Temperaturen sind in Celsiusgraden angegeben.
<I>Beispiel</I> 30 Teile der Diazoverbindung, welche man erhält, wenn man 12 Teile 4,4'-Diamino-3,3'-methoxy-1,1'- diphenyl tetrazotiert und mit 15 Teilen 1-Hydroxy- naphthalin-4,6-disulfonsäure asymmetrisch kuppelt, werden in 900 Teilen Wasser von 20 angerührt, mit einer Lösung von 25 Teilen Natriumcarbonat in 200 Teilen Wasser von 20 versetzt und hernach eine Lösung von 16 Teilen 1-Hydroxynaphthalin-3,6-disul- fonsäure, 25 Teilen Natriumcarbonat in 500 Teilen Wasser,
100 Teilen Pyridin und 10 Teilen einer 30 oioigen wässrigen Natriumhydroxydlösung zugegeben und 16 Stunden bei 20 gerührt. Darauf lässt man in nerhalb von 1'l2 Stunden 1800 Teile Äthylalkohol zu- fliessen, rührt 12 Stunden weiter und erhitzt die Kupp lungsmasse auf 75 , lässt auf 20 abkühlen und fil triert. Der Filterkuchen wird mit 400 Teilen 50 o/oigem Athylalkohol gewaschen.
Der Filterrückstand wird nun in 1600 Teilen Was ser und 30 Teilen Diäthanolamin bei 75 unter Rühren gelöst. Innerhalb 15 Minuten lässt man eine Lösung, bestehend aus 30 Teilen Kupfersulfat in 200 Teilen Wasser und 30 Teilen 25 o/oigem Ammoniak, zutrop- fen. Nachdem während 16 Stunden bei 96-98 gerührt wurde, wird die Masse auf 20 gekühlt, mit 400 Teilen Kaliumchlorid versetzt, 2 Stunden gerührt und filtriert. Nach dem Trocknen bei 110 erhält man 50 Teile eines blauen Farbstoffs.
Zum Färben verfährt man wie folgt: Man löst 0,1 Teile des kupferhaltigen Disazofarb- stoffs des Beispiels in 300 Teilen kalkfreiem Wasser. In dieser Flotte färbt man 10 Teile angenetztes Baum wolltuch, indem man das Bad, beginnend bei einer Temperatur von 30', innerhalb von 30 Minuten bei 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 o/oigen 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 Färbeguts 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 using compounds of the formula
EMI0001.0008
where A is a mono- or binuclear aromatic radical and R.
mean a diazonium group, couples with any coupling component and selects the individual components to be used to build up the dyes so that they contain at least the number of solubilizing groups necessary for the water solubility of the dyes.
In the ortho position to the azo bridges linked with 1-hydroxynaphthalene-4,6-disulphonic acid, the components can have a substituent capable of forming metal complexes. contain. The dyes obtained can be treated as they are with copper- or nickel-releasing agents.
Compounds of the formula (I) in which R is the remainder of a diazonium group can be made from the corresponding amino dyes by diazotization and then combined with a coupling component, whereby a Mittelkompo component can be used; the coupling products obtained in this way can be further diazotized and coupled with a final component.
Possible middle components are: aminobenzene, 3-amino-1-methylbenzene, 3-amino-4-methoxy-1-methylbenzene, 3-amino-1,4-dimethylbenzene, 3-amino-1-acetyl-aminobenzo @ 3- Amino-1-sulfoacetylaminubenzene, 1-aminonaphthalene \ ,. 1-aminonaphthalene-6- or -7-sulfonic acid, 1-amino-2-methoxy- or -2-ethoxynaphthalene-6-sulfonic acid. As final components come z.
B. in question salicylic acid, cresotinic acid, 1- or -2-hydroxy-naphthaEn and 'their mono-, di- and trisulfonic acids, such as 1-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 saturation, pyrazolones and their substitution products such as 1-phenyl-3-methyl-5 -pyrazzo-ion, 1-phenyl-3-methyl, 5-pyrazolon-3 "-sulfonic acid or -4:
-sulfonic acid or - <B> Y </B>,. 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- pyrazolon, etc. as well as amino-hydroxynaphthalin mono- and disulfonic acids and their acetyl anüno- and arylamino derivatives, z :.
B. 2r.Amino-5-hydroxynaphthalene 7-sulfonic acid, whose. Acetyl-, berzoyl =, phenyl-; Anisidyl ,. Chloroacetyl, crotonyl or urea derivatives.
1-amino-8-hydroxynaphthalene-4-sulfonic acid, its acetyl, benzoyl or phenyl derivatives, 1-amino-8-hydroxynaphthalene-3,6- or -2,4-disulfonic acid, 2 -Amino-5-hydroxy-naphthalene-7-sulfonic acid, 2-amino-8-hydroxynaphthalene-6-sulfonic acid and their acetyl, benzoyl and phenyl derivatives, acetoacetyl aminobenzene,
1-acetoacetylamino-2-, -3- or -4-methyl-, -methoxy- or -chlorobenzene and their sulfonic acids and barbituric acid.
Other final components are e.g. B. monoazo dyes with. a coupling point, such as
EMI0002.0001
Azines like
EMI0002.0004
Instead of a final component, middle components can also be considered.
The coupling products obtained from a connection of the formula (I) and a central component can be further diazotized in the usual way and with any final component such. B. the above-mentioned, preferably in the presence of pyridine or dimethylformamide, coupled and the resulting dyes, if they contain metallizable groups, can be converted into the metal complex compound in substance.
The diazoazo compound of the formula (I) can be obtained, for example, by tetrazotizing 1 mole of a diamine and coupling it on one side with 1 mole of 1-hydroxynaphthylialin-4,6-disulfonic acid.
Particularly suitable diamines are: 4,4'-diamino-3,3'-dimethoxy-1,1'-diphenyl, 4,4'-dianiino-3,3'-dicarboxy-1,1'-diphenyl , 4,4'-diamino-3,3'-dicarboxymethoxy-1,1-diphenyl, 4,4'-diamino-3,3'-dihydroxy-1,1'-diphenyl. These diazonium compounds can, in the same way as described above,
are combined with a central component and then further diazo- tated and combined with a final component or combined directly with one of the final components listed above, whereupon the resulting dyes, if they contain metallizable groups, are metallized in substance.
The treatment with copper- or nickel-releasing compounds can be carried out in substance in very different ways, e.g. 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 diethanolamine, 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 by the process are used for dyeing, padding or printing cotton and fibers made from regenerated cellulose in very real color shades that vary depending on the structure. In particular, very lightfast blue, gray, green, brown and red colorations are obtained.
The wet fastness properties can be further improved by treating the dyeings with polyalkylene polyamines at the same time or afterwards.
The dyeings on natural and regenerated cellulose have very good lightfastness and 1 "cup fastness such as wash, water, perspiration, seawater, wet iron fastness, water drop fastness, etc. They also have good fastness to release, formaldehyde, alkali and acid fastness The new dyes reserve cellulose acetate, wool, silk, nylon, perlon, acrylic and polyester fibers very well. The gas resistance is excellent.
In the following examples, parts are parts by weight and percentages are percentages by weight. The temperatures are given in degrees Celsius.
<I> Example </I> 30 parts of the diazo compound, which is obtained when 12 parts of 4,4'-diamino-3,3'-methoxy-1,1'-diphenyl are tetrazotized and 15 parts of 1-hydroxy naphthalene-4,6-disulfonic acid coupling asymmetrically, are mixed in 900 parts of water of 20, treated with a solution of 25 parts of sodium carbonate in 200 parts of water of 20 and then a solution of 16 parts of 1-hydroxynaphthalene-3,6-disul- fonsäure, 25 parts of sodium carbonate in 500 parts of water,
100 parts of pyridine and 10 parts of a 30% aqueous sodium hydroxide solution were added and the mixture was stirred at 20 for 16 hours. 1800 parts of ethyl alcohol are then allowed to flow in within 1 1/2 hours, the mixture is stirred for a further 12 hours and the coupling compound is heated to 75, allowed to cool to 20 and filtered. The filter cake is washed with 400 parts of 50% ethyl alcohol.
The filter residue is now dissolved in 1600 parts of water and 30 parts of diethanolamine at 75 with stirring. A solution consisting of 30 parts of copper sulfate in 200 parts of water and 30 parts of 25% ammonia is allowed to drop in over the course of 15 minutes. After stirring for 16 hours at 96-98, the mass is cooled to 20, mixed with 400 parts of potassium chloride, stirred for 2 hours and filtered. After drying at 110, 50 parts of a blue dye are obtained.
The procedure for coloring is as follows: 0.1 part of the copper-containing disazo dye of the example is dissolved in 300 parts of lime-free water. In this liquor, 10 parts of wetted cotton cloth are dyed by heating the bath, starting at a temperature of 30 ', to 100 over the course of 30 minutes and holding it at this temperature for 15 minutes. During the dyeing process, 3-4 parts of sodium sulfate 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. Post-treating the dyed material with a basic, cation-active copper complex compound significantly improves the fastness properties of the dye.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH259065A CH487978A (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 |
| CH259065A CH487978A (en) | 1960-04-08 | 1960-04-08 | Process for the production of disazo and polyazo dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH487978A true CH487978A (en) | 1970-03-31 |
Family
ID=25690859
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH259065A CH487978A (en) | 1960-04-08 | 1960-04-08 | Process for the production of disazo and polyazo dyes |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH487978A (en) |
-
1960
- 1960-04-08 CH CH259065A patent/CH487978A/en not_active IP Right Cessation
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