DE1111316B - Process for the preparation of water-insoluble monoazo dyes - Google Patents
Process for the preparation of water-insoluble monoazo dyesInfo
- Publication number
- DE1111316B DE1111316B DEC17605A DEC0017605A DE1111316B DE 1111316 B DE1111316 B DE 1111316B DE C17605 A DEC17605 A DE C17605A DE C0017605 A DEC0017605 A DE C0017605A DE 1111316 B DE1111316 B DE 1111316B
- Authority
- DE
- Germany
- Prior art keywords
- water
- bis
- cyanoethyl
- amino
- monoazo dyes
- 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.)
- Pending
Links
- 239000000975 dye Substances 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 6
- 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 title claims description 3
- NSVHSAUVIFTVPN-UHFFFAOYSA-N 3-[n-(2-cyanoethyl)anilino]propanenitrile Chemical compound N#CCCN(CCC#N)C1=CC=CC=C1 NSVHSAUVIFTVPN-UHFFFAOYSA-N 0.000 claims description 5
- 230000008878 coupling Effects 0.000 claims description 5
- 238000010168 coupling process Methods 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 2
- 150000001555 benzenes Chemical class 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- -1 N, N-bis (cyanoethyl) -l-amino-2,5-dimethylbenzene Chemical compound 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- WAKXJJFBKKMVOL-UHFFFAOYSA-N 3-[n-(2-cyanoethyl)-2-methoxy-5-methylanilino]propanenitrile Chemical compound COC1=CC=C(C)C=C1N(CCC#N)CCC#N WAKXJJFBKKMVOL-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FOSMJPANNXAZFB-UHFFFAOYSA-N 3-[3-chloro-n-(2-cyanoethyl)anilino]propanenitrile Chemical compound ClC1=CC=CC(N(CCC#N)CCC#N)=C1 FOSMJPANNXAZFB-UHFFFAOYSA-N 0.000 description 1
- MKNCWYPMMGPLLE-UHFFFAOYSA-N 3-[n-(2-cyanoethyl)-3-methoxyanilino]propanenitrile Chemical compound COC1=CC=CC(N(CCC#N)CCC#N)=C1 MKNCWYPMMGPLLE-UHFFFAOYSA-N 0.000 description 1
- KOLCFYBQZNXWET-UHFFFAOYSA-N 3-[n-(2-cyanoethyl)-3-methylanilino]propanenitrile Chemical compound CC1=CC=CC(N(CCC#N)CCC#N)=C1 KOLCFYBQZNXWET-UHFFFAOYSA-N 0.000 description 1
- YBAZINRZQSAIAY-UHFFFAOYSA-N 4-aminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1 YBAZINRZQSAIAY-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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 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 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
-
- 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
- D06P1/02—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 azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
C 17605 IVb/22aC 17605 IVb / 22a
BEKANNTMACHXJNG
DER ANMELDUNG
UND AUSGABE DER
AUSLEGESCHRIFT: 20. JULI 1961 ANNOUNCEMENTXJNG
THE REGISTRATION
AND ISSUE OF THE
EDITORIAL: JULY 20, 1961
Es wurde gefunden, daß man zu wertvollen, wasserunlöslichen Azofarbstoffen gelangt, wenn man die Diazo Verbindung von l-Amino-4-cyanbenzol mit einem in p-Stellung zur Aminogruppe kuppelnden N,N-Bis-(cyanäthyl)-aminobenzol, das im Benzolkern weitere nicht wasserlöslichmachende Substituenten aufweisen kann, vereinigt.It has been found that valuable, water-insoluble Azo dyes are obtained by using the diazo compound of l-amino-4-cyanobenzene an N, N-bis (cyanoethyl) aminobenzene coupling in the p-position to the amino group, which is in the benzene nucleus may have further non-water-solubilizing substituents, combined.
Als Beispiele geeigneter Azokomponenten seien genannt:Examples of suitable azo components are:
N,N-Bis-(cyanäthyl)-aminobenzol,
N,N-Bis-(cyanäthyl)-l-amino-3-methylbenzol,
N,N-Bis-(cyanäthyl)-l-amino-3-methoxybenzol,
l^N-Bis-icyanäthylH-amino-S-acetylaminobenzol,
N, N-bis (cyanoethyl) aminobenzene,
N, N-bis (cyanoethyl) -l-amino-3-methylbenzene,
N, N-bis (cyanoethyl) -l-amino-3-methoxybenzene,
l ^ N-bis-icyanäthylH-amino-S-acetylaminobenzene,
N,N-Bis-(cyanäthyl)-l-amino-3-chlorbenzol,
N,N-Bis-(cyanäthyl)-l-amino-2,5-dimethyibenzol, N,N-Bis-(cyanäthyl)-l-amino-2-methoxy
5-methylbenzol.N, N-bis (cyanoethyl) -l-amino-3-chlorobenzene,
N, N-bis (cyanoethyl) -l-amino-2,5-dimethylbenzene, N, N-bis- (cyanoethyl) -l-amino-2-methoxy
5-methylbenzene.
Die genannten Azokomponenten sind zum Teil bekannte Verbindungen und können nach bekannten Verfahren, beispielsweise durch Umsetzen der entsprechenden Bischloräthylverbindung mit einem Alkalicyanid (J. ehem. Soc, 1934, S. 1536) oder durch Umsetzen der entsprechenden Aminobenzole mit Acrylnitril, erhalten werden.Some of the azo components mentioned are known compounds and can be prepared according to known ones Process, for example by reacting the corresponding bischloroethyl compound with an alkali metal cyanide (J. former Soc, 1934, p. 1536) or by reacting the corresponding aminobenzenes with Acrylonitrile.
Die Diazotierung der erwähnten Diazokomponenten kann nach an sich bekannten Verfahren, z. B. mit Hilfe von Mineralsäure, insbesondere Salzsäure und Natriumnitrit oder z. B. mit einer Lösung von Nitrosylschwefelsäure in konzentrierter Schwefelsäure erfolgen.The diazotization of the diazo components mentioned can be carried out by methods known per se, for. B. with the help of mineral acid, especially hydrochloric acid and sodium nitrite or z. B. with a solution of Nitrosylsulfuric acid can be carried out in concentrated sulfuric acid.
Die Kupplung kann ebenfalls in an sich bekannter Weise, z. B. in neutralem bis saurem Mittel, gegebenenfalls in Gegenwart von Natriumacetat oder ähnlichen, die Kupplungsgeschwindigkeit beeinflussenden Puffersubstanzen oder Katalysatoren, wie Pyridin bzw. dessen Salzen, vorgenommen werden.The coupling can also be carried out in a manner known per se, for. B. in neutral to acidic agents, if appropriate in the presence of sodium acetate or similar buffer substances which influence the coupling rate or catalysts such as pyridine or its salts are made.
Nach erfolgter Kupplung können die entstandenen Farbstoffe leicht, z. B. durch Filtration, abgetrennt werden, da sie in Wasser praktisch unlöslich sind.After coupling, the resulting dyes can easily, for. B. by filtration, separated as they are practically insoluble in water.
Die erhaltenen Azofarbstoffe eignen sich vorzüglich zum Färben und Bedrucken von Gebilden, beispielsweise aus Polyamiden, insbesondere aber von Fasern aus Acetatkunstseide, Triacetat und Polyäthylenterephthalat. The azo dyes obtained are particularly suitable for dyeing and printing structures, for example made of polyamides, but especially of fibers made of acetate rayon, triacetate and polyethylene terephthalate.
Die auf den genannten Gebilden mit den Farbstoffen erhaltenen Färbungen zeichnen sich durch Reinheit und Lebhaftigkeit ihres Farbtones und durch gute Allgemeinechtheitseigenschaften, insbesondere durch eine hohe Sublimier- und Lichtechtheit aus. Gegenüber dem in der USA.-Patentschrift 2 782 187 beschriebenen Farbstoff, welcher an Stelle einer Cyan-Verfahren zur Herstellung von wasserunlöslichen MonoazofarbstoffenThe dyeings obtained with the dyes on the structures mentioned are distinguished Purity and liveliness of their hue and good general fastness properties, in particular characterized by high sublimation and lightfastness. Compared to that in U.S. Patent 2,782,187 described dye, which instead of a cyan method of manufacture of water-insoluble monoazo dyes
Anmelder:Applicant:
CIBA Aktiengesellschaft, Basel (Schweiz)CIBA Aktiengesellschaft, Basel (Switzerland)
Vertreter: Dipl.-Ing. E. Splanemann, Patentanwalt, Hamburg 36, Neuer Wall 10Representative: Dipl.-Ing. E. Splanemann, patent attorney, Hamburg 36, Neuer Wall 10
Beanspruchte Priorität: Schweiz vom 11. Oktober 1957Claimed priority: Switzerland of October 11, 1957
Dr. Paul Rhyner und Dr. Hugo JlIy, Basel (Schweiz),Dr. Paul Rhyner and Dr. Hugo JlIy, Basel (Switzerland),
sind als Erfinder genannt wordenhave been named as inventors
gruppe eine Nitrogruppe aufweist, zeigen die erfindungsgemäß erhaltenen Farbstoffe den Vorzug, für Cellulosetriacetat ein bedeutend besseres Ziehvermögen aufzuweisen und außerdem Färbungen von besserer Lichtechtheit zu ergeben.group has a nitro group, the dyes obtained according to the invention show the preference for Cellulose triacetate have a significantly better drawability and also colorations of to give better lightfastness.
CH2CH2CNCH 2 CH 2 CN
NC-NC-
-N = N--N = N-
>—N> —N
CH2CH2CNCH 2 CH 2 CN
11,8 Teile l-Amino-4-cyanbenzol werden in 200 Teilen 2n-Salzsäure gelöst, mit Eis auf 0 bis 5° C gekühlt und mit 25 Teilen 4 n-Natriumnitritlösung versetzt.11.8 parts of 1-amino-4-cyanobenzene are dissolved in 200 parts of 2N hydrochloric acid, with ice to 0 to 5 ° C cooled and mixed with 25 parts of 4N sodium nitrite solution.
Die so erhaltene Diazolösung läßt man in eineThe diazo solution thus obtained is left in a
Lösung von 19,9 Teilen N,N-Bis-(cyanäthyl)-aminobenzol in 100 Teile konzentrierte Salzsäure fließen.A solution of 19.9 parts of N, N-bis (cyanoethyl) aminobenzene in 100 parts of concentrated hydrochloric acid flow.
Durch Zugabe von gesättigter Natriumacetatlösung fällt der Farbstoff aus.The dye precipitates by adding saturated sodium acetate solution.
Der Farbstoff färbt Acetat-, Polyamid-, Triacetat-The dye dyes acetate, polyamide, triacetate
und Polyesterfasern in reinen gelben Tönen. Die Färbungen auf Polyesterfasern zeichnen sich durch gute Licht- und Sublimierechtheit aus. Ersetzt manand polyester fibers in pure yellow tones. The dyeings on polyester fibers are distinguished good lightfastness and sublimation fastness. Replace one
die Azokomponente durch N5N - Bis - (cyanäthyl)-l-amino-3-methylbenzol oder N,N-Bis-(cyanäthyl)-l-amino-3-methyl-6-methoxybenzol, so kommt man zu ähnlichen Farbstoffen.the azo component by N 5 N - bis (cyanoethyl) -l-amino-3-methylbenzene or N, N-bis- (cyanoethyl) -l-amino-3-methyl-6-methoxybenzene, one arrives at similar dyes.
Ig des mit 1,5 g Sulfitablauge oder Dinaphthylmethandisulfonsäure oder einer Fettalkoholäthylen-Ig des with 1.5 g of sulphite waste liquor or dinaphthylmethanedisulphonic acid or a fatty alcohol ethylene
109 648/321109 648/321
oxydkondensationsverbindung verpasteten, gemäß Absatz 1 und 2 erhältlichen Farbstoffes wird mit Wasser auf 4000 cm3 verdünnt, wobei noch 1 ccm/Liter Essigsäure (4O°/o) und 1 g/Liter einer Fettalkoholäthylenoxydkondensationsverbindung zugegeben werden. In diesem Färbebad färbt man 100 g Polyesterfasergarn V2 bis 1 Stunde bei 115 bis 132 0C, wobei eine tiefe Gelbfärbung von sehr guter Licht- und Sublimierechtheit erhalten wird.Oxydkondensationsverbindungen pasted, according to paragraphs 1 and 2 available dye is diluted with water to 4000 cm 3 , 1 ccm / liter of acetic acid (40%) and 1 g / liter of a fatty alcohol ethylene oxide are added. In this dyebath, 100 g of polyester fiber yarn V are dyed for 2 to 1 hour at 115 to 132 ° C., a deep yellow coloration of very good lightfastness and sublimation fastness being obtained.
Claims (2)
Deutsche Patentschriften Nr. 648 768, 924 763;
Französische Patentschrift Nr. 1 071 728;
USA.-Patentschrift Nr. 2 782 187.Considered publications:
German Patent Nos. 648 768, 924 763;
French Patent No. 1,071,728;
U.S. Patent No. 2,782,187.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1111316X | 1957-10-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1111316B true DE1111316B (en) | 1961-07-20 |
Family
ID=4558093
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC17605A Pending DE1111316B (en) | 1957-10-11 | 1958-10-03 | Process for the preparation of water-insoluble monoazo dyes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1111316B (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE648768C (en) * | 1934-02-23 | 1937-08-11 | Chemische Ind Ges | Process for the production of azo dyes |
| FR1071728A (en) * | 1951-09-07 | 1954-09-03 | Sandoz Ag | Mono-azo dyes and their preparation |
| DE924763C (en) * | 1951-09-07 | 1955-03-07 | Sandoz Ag | Process for the preparation of monoazo dyes |
| US2782187A (en) * | 1954-10-01 | 1957-02-19 | Du Pont | Azo dyes for pollyester fiber |
-
1958
- 1958-10-03 DE DEC17605A patent/DE1111316B/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE648768C (en) * | 1934-02-23 | 1937-08-11 | Chemische Ind Ges | Process for the production of azo dyes |
| FR1071728A (en) * | 1951-09-07 | 1954-09-03 | Sandoz Ag | Mono-azo dyes and their preparation |
| DE924763C (en) * | 1951-09-07 | 1955-03-07 | Sandoz Ag | Process for the preparation of monoazo dyes |
| US2782187A (en) * | 1954-10-01 | 1957-02-19 | Du Pont | Azo dyes for pollyester fiber |
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