DE1940685C3 - Disperse dyes of the amino pyrazole series, process for their manufacture and use - Google Patents
Disperse dyes of the amino pyrazole series, process for their manufacture and useInfo
- Publication number
- DE1940685C3 DE1940685C3 DE19691940685 DE1940685A DE1940685C3 DE 1940685 C3 DE1940685 C3 DE 1940685C3 DE 19691940685 DE19691940685 DE 19691940685 DE 1940685 A DE1940685 A DE 1940685A DE 1940685 C3 DE1940685 C3 DE 1940685C3
- Authority
- DE
- Germany
- Prior art keywords
- parts
- dyes
- manufacture
- disperse dyes
- amino pyrazole
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 title claims description 3
- 239000000986 disperse dye Substances 0.000 title claims 2
- 238000000034 method Methods 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000000975 dye Substances 0.000 description 19
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
- -1 carbomethoxy, carboethoxy Chemical group 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- MUHLVSZIVTURCZ-UHFFFAOYSA-N 2-amino-3-bromo-5-nitrobenzonitrile Chemical compound NC1=C(Br)C=C([N+]([O-])=O)C=C1C#N MUHLVSZIVTURCZ-UHFFFAOYSA-N 0.000 description 2
- ZVNYYNAAEVZNDW-UHFFFAOYSA-N 2-phenylpyrazol-3-amine Chemical compound NC1=CC=NN1C1=CC=CC=C1 ZVNYYNAAEVZNDW-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Chemical group 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 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
- 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
- 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
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- AVMNFQHJOOYCAP-UHFFFAOYSA-N acetic acid;propanoic acid Chemical compound CC(O)=O.CCC(O)=O AVMNFQHJOOYCAP-UHFFFAOYSA-N 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
- 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
- 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
- WKGMRNVMTBOZIS-UHFFFAOYSA-N methyl 2-amino-3-bromo-5-nitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=CC(Br)=C1N WKGMRNVMTBOZIS-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
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
- D06P1/18—Azo 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
- C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
- C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone
-
- E—FIXED CONSTRUCTIONS
- E04—BUILDING
- E04B—GENERAL BUILDING CONSTRUCTIONS; WALLS, e.g. PARTITIONS; ROOFS; FLOORS; CEILINGS; INSULATION OR OTHER PROTECTION OF BUILDINGS
- E04B5/00—Floors; Floor construction with regard to insulation; Connections specially adapted therefor
- E04B5/44—Floors composed of stones, mortar, and reinforcing elements
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Architecture (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Electromagnetism (AREA)
- Civil Engineering (AREA)
- Structural Engineering (AREA)
- Dispersion Chemistry (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Description
H,NH, N
4. Verfahren zur Herstellung von Farbstoffen der im Anspruch 1 angegebenen Formel, dadurch gekennzeichnet, daß man Diazoverbindungen von Aminen der allgemeinen Formel4. Process for the preparation of dyes of the formula given in claim 1, characterized characterized in that one diazo compounds of amines of the general formula
und Y die im Anspruch 1 angegebenen Bedeutungen haben.and Y have the meanings given in claim 1.
5. Verwendung der Farbstoffe der im Anspruch 1 angegebenen Formel zum Färben von Textilmaterial aus Polyestern.5. Use of the dyes of the formula given in claim 1 for dyeing textile material made of polyesters.
Die Erfindung betrifft wertvolle neue Monoazofarbstoffe der Aminopyrazolreihe der allgemeinen FormelThe invention relates to valuable new monoazo dyes of the aminopyrazole series of the general formula
Q1N-/"S-N=NQ 1 N - / "SN = N
in der X ein Chlor- oder Bromatom oder eine Carbomethoxy-, Carboäthoxy-, Nitro- oder Cyangruppe und Y ein Wasserstoff-, Chlor- oder Bromatom ist.in which X is a chlorine or bromine atom or a carbomethoxy, carboethoxy, nitro or cyano group and Y is hydrogen, chlorine, or bromine.
2. Farbstoffe gemäß Anspruch 1 der allgemeinen Formel2. Dyestuffs according to Claim 1 of the general formula
H,NH, N
in der X1 eine Carbomethoxy-, Carboäthoxy- oder
Cyangruppe und Y1 ein Wasserstoff-, Chlor- oder Bromatom ist.
3. Farbstoff gemäß Anspruch 1 und 2 der Formelin which X 1 is a carbomethoxy, carboethoxy or cyano group and Y 1 is a hydrogen, chlorine or bromine atom.
3. Dyestuff according to Claim 1 and 2 of the formula
45 in der X ein Chlor- oder Bromatom oder eine Carbomethoxy-, Carboäthoxy-, Nitro- oder Cyangruppe 45 in which X is a chlorine or bromine atom or a carbomethoxy, carboethoxy, nitro or cyano group
und Y ein Wasserstoff-, Chlor- oder Bromatom sind.and Y is hydrogen, chlorine or bromine.
Diazokomponenten zur Herstellung der neuenDiazo components to produce the new
Farbstoffe sind z. B. 2-Cyan-4-nitranilin, 2-Cyan-6-chlor-4-nitranilin, 2-Cyan-6-brom-4-nitranilin, 2,6-Dichlor - 4 - nitranilin, 2,6 - Dibrom - 4 - nitranilin, 2-Chlor-6-brom-4-nitranüin, 2-Carbomethoxy-4 - nitranilin, 2 - Carboäthoxy - 4 - nitranilin oder 2-Carbomethoxy-6-brom-4-nitranilin.Dyes are z. B. 2-cyano-4-nitroaniline, 2-cyano-6-chloro-4-nitroaniline, 2-cyano-6-bromo-4-nitroaniline, 2,6-dichloro - 4 - nitroaniline, 2,6 - dibromo - 4 - nitroaniline, 2-chloro-6-bromo-4-nitranuine, 2-carbomethoxy-4 - nitroaniline, 2 - carboethoxy - 4 - nitroaniline or 2-carbomethoxy-6-bromo-4-nitroaniline.
Von besonderer technischer Bedeutung sind Farbstoffe der allgemeinen FormelDyes of the general formula are of particular technical importance
N=NN = N
H2NH 2 N
mit l-Phenyl-5-aminopyrazol kuppelt, wobei Xcouples with l-phenyl-5-aminopyrazole, where X
55 in der X1 eine Carbomethoxy-, Carboäthoxy- oder
Cyangruppe und Y1 ein Wasserstoff-, Chlor- oder Bromatom sind.
Die neuen Farbstoffe sind Gelb bis Orange und eignen sich zum Färben von synthetischen, linearen
Polyestern sowohl nach der Carrier- als auch nach der HT-Methode. Man erzielt dabei Färbungen mit
ausgezeichneten Echtheiten. 55 in which X 1 is a carbomethoxy, carboethoxy or cyano group and Y 1 is a hydrogen, chlorine or bromine atom.
The new dyes range from yellow to orange and are suitable for dyeing synthetic, linear polyesters using both the carrier and the HT method. This produces dyeings with excellent fastness properties.
Gegenüber nächstvergleichbaren aus der deutschen Patentschrift 1 282 212 bekannten Farbstoffen zeichnen sich die neuen Farbstoffe durch besseres Ziehvermögen und besseren Farbaufbau aus. Bei der Ähnlichkeit der Farbstoffe war dieses Verhalten über-Compared to the closest comparable dyes known from German Patent 1,282,212 the new dyes are characterized by better drawability and better color structure. In the The similarity of the dyes was beyond this behavior.
raschend. Gegenüber Farbstoffen, die in der britischen Patentschrift 1034489 beschrieben sind, haben die neuen Farbstoffe unvorhersehbare Vorteile in der Lichtechtheitsurprising. Compared to dyes, which are described in British patent 1034489, have the new dyes have unpredictable advantages in terms of lightfastness
Zur Herstellung der neuen Farbstoffe kann man Diazoverbindungen von Aminen der allgemeinen FormelTo prepare the new dyes one can use diazo compounds of amines of the general formula
vermindertem Druck bei 600C getrocknet
erhält 9,0 Teile des Farbstoffs der Formeldried at 60 ° C. under reduced pressure
contains 9.0 parts of the dye of the formula
-N=N-N = N
O2NO 2 N
NH,NH,
IO H2N IO H 2 N
nach bekannten Methoden mit l-Pheiiyl-5-aminopyrazol kuppeln.according to known methods with l-phenyl-5-aminopyrazole couple.
In den folgenden Beispielen beziehen sich Angaben über Teile und Prozente, sofern nicht anders vermerkt, auf das Gewicht.In the following examples, parts and percentages relate, unless otherwise stated, on weight.
8,46 Teile 2-Cyan-4-nitro-6-bromanilin (0,035 Mol) werden bei 10 bis 15° C in 41 Teile konzentrierte Schwefelsäure eingetragen. Sobald das Amin gelöst ist, kühlt man auf 5° C ab und fügt allmählich 30 Teile eines Eisessig- Propionsäure-Gemisches (17: 3) zu.8.46 parts of 2-cyano-4-nitro-6-bromoaniline (0.035 mol) are introduced into 41 parts of concentrated sulfuric acid at 10 to 15 ° C. Once the amine is dissolved is, it is cooled to 5 ° C and gradually adds 30 parts of a glacial acetic acid-propionic acid mixture (17: 3).
Dann werden bei 0 bis 5° C langsam 9 Teile Nitrosylschwefelsäure zugegeben und 3 Stunden bei dieser Temperatur gerührt. Anschließend gibt man die Diazolösung zu einer gekühlten Lösung von 5,8 Teilen (0,035 Mol) l-Phenyl-5-amino-pyrazol in 150 Teilen Methanol und 50 Teilen Wasser. Nach beendeter Zugabe hält man 1 Stunde bei 0 bis 5° C, saugt den ausgefallenen Farbstoff ab, wäscht mit Wasser neutral und trocknet bei 6O0C unter vermindertem Druck.Then 9 parts of nitrosylsulfuric acid are slowly added at 0 to 5 ° C. and the mixture is stirred at this temperature for 3 hours. The diazo solution is then added to a cooled solution of 5.8 parts (0.035 mol) of 1-phenyl-5-aminopyrazole in 150 parts of methanol and 50 parts of water. After completion of the addition is kept for 1 hour at 0 to 5 ° C, filtered off with suction the precipitated dye, washed neutral with water and dried at 6O 0 C under reduced pressure.
Man erhält 13,7 Teile des Farbstoffs der Formel13.7 parts of the dye of the formula are obtained
4040
4545
der auf Polyesterfasern ebenfalls sehr echte Orangefärbungen ergibtwhich also gives very real orange colorations on polyester fibers
Analog der angegebenen Arbeitsweise erhält man mit den Diazokomponenten der nachstehenden Tabelle Farbstoffe, die Polyester-Textilmaterial im angegebenen Farbton färben:The diazo components in the table below are obtained analogously to the procedure given Dyes that dye polyester textile material in the specified shade:
5555
der Polyesterfasern in klaren Orangetönen mit allgemein sehr guten Echtheiten färbt.the polyester fibers in clear orange tones with generally very good fastness properties.
6060
5,9 Teile ^-Cyan-^-nitro-o-chlor-anilin (0,03 Mol) werden wie im Beispiel 1 beschrieben diazotiert. Die Diazolösung wird dann langsam bei 0 bis 5° C zu der Lösung von 4,8 Teilen l-Phenyl-5-amino-pyrazol (0,03 Mol) in 100 Teilen Methanol und 50 Teilen Wasser zugegeben. Man hält 1 Stunde bei dieser Temperatur. Dann wird der ausgefallene Farbstoff abgesaugt, mit Wasser neutral gewaschen und unter5.9 parts of ^ -Cyan - ^ - nitro-o-chloro-aniline (0.03 mol) are diazotized as described in Example 1. The diazo solution is then slowly added at 0 to 5 ° C the solution of 4.8 parts of 1-phenyl-5-aminopyrazole (0.03 mol) in 100 parts of methanol and 50 parts Water added. It is kept at this temperature for 1 hour. Then the precipitated dye Sucked off, washed neutral with water and taken under
Ο,Ν-^f 1>—NH2 Ο, Ν- ^ f 1> —NH 2
O2NO 2 N
O2NO 2 N
NH,NH,
COOCH3 COOCH 3
O2N-/O 2 N- /
COOCH,COOCH,
Farbton auf PolyesterColor shade on polyester
GelborangeYellow orange
GelborangeYellow orange
GelborangeYellow orange
GelborangeYellow orange
GelborangeYellow orange
GelborangeYellow orange
GelborangeYellow orange
Claims (1)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE754401D BE754401A (en) | 1969-08-09 | AMINOPYRAZOLIC SERIES DISPERSED DYES | |
| DE19691940685 DE1940685C3 (en) | 1969-08-09 | 1969-08-09 | Disperse dyes of the amino pyrazole series, process for their manufacture and use |
| CH406873A CH553840A (en) | 1969-08-09 | 1970-07-16 | PROCESS FOR THE PREPARATION OF DISPERSION DYES OF THE AMINOPYRAZOLE SERIES. |
| FR7027978A FR2057082B1 (en) | 1969-08-09 | 1970-07-29 | |
| GB3817870A GB1310564A (en) | 1969-08-09 | 1970-08-07 | Disperse dyes of the aminopyrazole series |
| JP6934370A JPS4812403B1 (en) | 1969-08-09 | 1970-08-10 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691940685 DE1940685C3 (en) | 1969-08-09 | 1969-08-09 | Disperse dyes of the amino pyrazole series, process for their manufacture and use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1940685A1 DE1940685A1 (en) | 1971-02-18 |
| DE1940685B2 DE1940685B2 (en) | 1973-04-05 |
| DE1940685C3 true DE1940685C3 (en) | 1973-10-31 |
Family
ID=5742437
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691940685 Expired DE1940685C3 (en) | 1969-08-09 | 1969-08-09 | Disperse dyes of the amino pyrazole series, process for their manufacture and use |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS4812403B1 (en) |
| BE (1) | BE754401A (en) |
| CH (1) | CH553840A (en) |
| DE (1) | DE1940685C3 (en) |
| FR (1) | FR2057082B1 (en) |
| GB (1) | GB1310564A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5145511U (en) * | 1974-10-02 | 1976-04-03 | ||
| JPS5148510U (en) * | 1974-10-08 | 1976-04-12 | ||
| JPS5297310U (en) * | 1976-01-20 | 1977-07-21 | ||
| JPS5297309U (en) * | 1976-01-20 | 1977-07-21 | ||
| JPS53120029U (en) * | 1977-03-02 | 1978-09-25 | ||
| JPS61185616U (en) * | 1985-05-13 | 1986-11-19 |
-
0
- BE BE754401D patent/BE754401A/en unknown
-
1969
- 1969-08-09 DE DE19691940685 patent/DE1940685C3/en not_active Expired
-
1970
- 1970-07-16 CH CH406873A patent/CH553840A/en not_active IP Right Cessation
- 1970-07-29 FR FR7027978A patent/FR2057082B1/fr not_active Expired
- 1970-08-07 GB GB3817870A patent/GB1310564A/en not_active Expired
- 1970-08-10 JP JP6934370A patent/JPS4812403B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2057082A1 (en) | 1971-05-07 |
| DE1940685A1 (en) | 1971-02-18 |
| BE754401A (en) | 1971-02-04 |
| JPS4812403B1 (en) | 1973-04-20 |
| CH553840A (en) | 1974-09-13 |
| DE1940685B2 (en) | 1973-04-05 |
| GB1310564A (en) | 1973-03-21 |
| FR2057082B1 (en) | 1974-07-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHV | Ceased/renunciation |