DE2110771A1 - Trisazo dyes - Google Patents
Trisazo dyesInfo
- Publication number
- DE2110771A1 DE2110771A1 DE19712110771 DE2110771A DE2110771A1 DE 2110771 A1 DE2110771 A1 DE 2110771A1 DE 19712110771 DE19712110771 DE 19712110771 DE 2110771 A DE2110771 A DE 2110771A DE 2110771 A1 DE2110771 A1 DE 2110771A1
- Authority
- DE
- Germany
- Prior art keywords
- dyes
- formula
- amino
- conh
- trisazo 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.)
- Granted
Links
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
- C09B35/38—Trisazo dyes ot the type
- C09B35/44—Trisazo dyes ot the type the component K being a hydroxy amine
- C09B35/46—Trisazo dyes ot the type the component K being a hydroxy amine the component K being an amino naphthol
- C09B35/467—D being derived from diaminodiaryl linked through CON<, SO2N<, CSN<
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
My/Pk LEVERKUSEN Etyerwerk '_;■ . IV1SrZ 1971My / Pk LEVERKUSEN Etyerwerk '_; ■ . IV 1 SrZ 1971
P»tent-AbteilungP »tent department
TrisazofarbstoffeTrisazo dyes
Gegenstand der vorliegenden Erfindung sind Trisazofarbstoffe der allgemeinen FormelThe present invention relates to trisazo dyes of the general formula
NH2 OH (I)NH 2 OH (I)
A-N=N-j^si^^s.-N=N-/ CA-CONH-// pA-N=N-BAN = Nj ^ si ^^ s.-N = N- / CA-CONH- // pA-N = NB
worinwherein
A = Rest einer aromatisch-carbocyclischen oder -heterocyclischen Diazokomponente,A = radical of an aromatic-carbocyclic or -heterocyclic Diazo component,
B = ggf. durch Alkyl substituiertes Hydroxyphenyl, Diaminophenyl oder Aminohydroxyphenyl undB = hydroxyphenyl, diaminophenyl or aminohydroxyphenyl optionally substituted by alkyl and
η = 1 oder 2,η = 1 or 2,
wobei die Ringe C und D weitere Substituenten aufweisen können.where the rings C and D can have further substituents.
Le A 13 620Le A13620
209838/1153209838/1153
Geeignete Reste A sind "beispielsweise Phenyl, Halogenphenyl wie Chlorphenyl, Bromphenyl, Alkylphenyl wie JYtethy!phenyl, Äthylphenyl, Alkoxyphenyl wie Methoxyphenyl, Äthoxyphenyl, Nitrophenyl, Sulfophenyl, der Rest der Dehydrothiotoluidinsulfosäure sowie Benzthiazolyl-(2),Suitable radicals A are, for example, phenyl and halophenyl such as chlorophenyl, bromophenyl, alkylphenyl such as Ytethy! phenyl, Ethylphenyl, alkoxyphenyl such as methoxyphenyl, ethoxyphenyl, Nitrophenyl, sulfophenyl, the remainder of the dehydrothiotoluidinsulfonic acid as well as benzothiazolyl- (2),
Geeignete Reste B sind beispielsweise Hydroxyphenyl, Hydroxymethy!phenyl, Hydroxy-äthy!phenyl, Aminohydroxyphenyl, Diaminophenyl, Diaminomethy!phenyl.Suitable radicals B are, for example, hydroxyphenyl, hydroxymethyl! Phenyl, Hydroxy-ethy-phenyl, amino-hydroxyphenyl, diaminophenyl, Diaminomethylphenyl.
Als Substituenten für die Ringe C und D seien beispielsweise erwähnt C^-C^-Alkyl wie Methyl, Äthyl, Propyl, Butyl sowie Halogen wie Chlor und Brom.Examples of substituents for the rings C and D are mentions C ^ -C ^ -alkyl such as methyl, ethyl, propyl, butyl as well Halogen such as chlorine and bromine.
Bevorzugte Farbstoffe sind dabei solche der FormelPreferred dyes are those of the formula
-N=SN- ß \ -CONH- ß \ -N=N-B-N = SN- ß \ -CONH- ß \ -N = NB
A'-N=N-A'-N = N-
LHUJLHUJ
(SO3H)n (SO 3 H) n
A' = Nitrophenyl, Halogenphenyl, insbesondere Chlorphenyl,A '= nitrophenyl, halophenyl, especially chlorophenyl,
Alkylphenyl, insbesondere Methylphenyl und B und η die in Formel (I) angegebene Bedeutung haben.Alkylphenyl, in particular methylphenyl, and B and η have the meaning given in formula (I).
Die neuen Farbstoffe der Formel (I) erhält man in an sich bekannter Weise durch saure Kupplung von Aminen der FormelThe new dyes of the formula (I) are obtained in a manner known per se by acidic coupling of amines of the formula
A-NH2 (III)A-NH 2 (III)
auf Aminohydroxynaphthalinsulfonsäuren der Formelon aminohydroxynaphthalenesulfonic acids of the formula
Le A 13 620 - 2 - Le A 13 620 - 2 -
209838/1153209838/1153
OH NH2 OH NH 2
(IV)(IV)
worin η = 1 oder 2 bedeutet, zu Monoazofarbstoffe!! der Formelwhere η = 1 or 2, to monoazo dyes !! the formula
NH2 OHNH 2 OH
A-N=N-A-N = N-
(SO3H)n (SO 3 H) n
(V)(V)
anschließende halbseitige Kupplung m.vt; einem tetrazotierten Amin der Formelsubsequent half-sided coupling w.vt; a tetrazotized amine the formula
- /~C~A -CONH-- / ~ C ~ A -CONH-
zu Disazofarbstoffen der Formelto disazo dyes of the formula
(VI)(VI)
NH2 OHNH 2 OH
A-N=N-A-N = N-
-N=N-rf C\-CONH-//D-N = N- rf C \ -CONH - // D
Xy (VII)X y (VII)
worin XÖ für ein Anion, bevorzugt das Anion einer anorganischen Säure wie Schwefelsäure oder Salzsäure steht und anschließende Kupplung mit Kupplungskomponentenwhere XÖ is an anion, preferably the anion of an inorganic one Acid such as sulfuric acid or hydrochloric acid and subsequent coupling with coupling components
B-H ' (VIII)B-H '(VIII)
worin B gegebenenfalls durch Alkyl substituiertes Hydroxyphenyl, Diaminophenyl oder Aminohydroxyphenyl bedeutet.in which B denotes hydroxyphenyl, diaminophenyl or aminohydroxyphenyl which is optionally substituted by alkyl.
Geeignete Amine (ill) sind beispielsweise Anilin, 2-Chloranilin, 3-Chlor-anilin, 4-Chlor-anilin, l-Aminobenzol-2-sulfonsäure, l-Amino-benzol-3-sulfonsäure, l-Aminobenzol-4-sulfonsäure,.lrAmino-2-methylbenzol, l-Amino-4-methyl-benzol, l-Amino-2-nitro-benzol, 1-Amino-4-nitrο-benzol, l-Amino-4-methoxy-benzol, Dehydrothiotoluidinsulfonsäure, 2-Aminobenzthiazol. Suitable amines (ill) are, for example, aniline, 2-chloroaniline, 3-chloro-aniline, 4-chloro-aniline, l-aminobenzene-2-sulfonic acid, l-amino-benzene-3-sulfonic acid, l-aminobenzene-4-sulfonic acid, .lr-amino-2-methylbenzene, l-amino-4-methyl-benzene, l-amino-2-nitro-benzene, 1-amino-4-nitro-benzene, l-amino-4-methoxy-benzene, Dehydrothiotoluidinesulfonic acid, 2-aminobenzothiazole.
Le A 13 620Le A13620
— 3 — 209838/1153- 3 - 209838/1153
Geeignete Amino-hydroxy-naphthalinsulfonsäuren (IV) sind beispielsweise l-Amino-8-hydroxy-naphthalin-3,6-disulfonsäure, l-Amino-8-hydroxy-naphthalin-4,6-disulfonsäure, l-Amino-8-hydroxy-naphthalin-4-sulfonsäure. Suitable amino-hydroxy-naphthalenesulfonic acids (IV) are for example l-amino-8-hydroxynaphthalene-3,6-disulfonic acid, l-amino-8-hydroxy-naphthalene-4,6-disulphonic acid, l-amino-8-hydroxy-naphthalene-4-sulphonic acid.
Geeignete Diamine (IV) sind beispielsweise:Suitable diamines (IV) are, for example:
4-Amino-bezoyl-4!-amino-anilid 4-Amino-2-chlor-benzoyl-4!-amino-anilid 4~Amino-3-methyl-benzoyl-4t-amino-anilid 4-Amino-benzoyl-4'-amino-2'-chlor-anilid 4'-Amino-benzoyl-4'-amino-3'-methyl-anilid.4-amino-bezoyl-4 ! -amino-anilide 4-amino-2-chloro-benzoyl-4 ! -amino-anilide 4 ~ amino-3-methyl-benzoyl-4 t -amino-anilide 4-amino-benzoyl-4'-amino-2'-chloro-anilide 4'-amino-benzoyl-4'-amino-3 '-methyl anilide.
Geeignete Kupplungskomponenten (VIII) sind beispielsweise Phenol, Methylphenol, Äthylphenol, 1,3-Diaminobenzol, l-Amino-3-hydroxybenzol, 1,3-Diamino-4-methylbenzol.Suitable coupling components (VIII) are, for example, phenol, methylphenol, ethylphenol, 1,3-diaminobenzene, 1-amino-3-hydroxybenzene, 1,3-diamino-4-methylbenzene.
Die Kupplung von (V) mit (VI) und von (VII) mit (VIII) erfolgt in an sich bekannter Weise in wässrig-alkalischem Medium.The coupling of (V) with (VI) and of (VII) with (VIII) takes place in an aqueous-alkaline manner in a manner known per se Medium.
Die neuen Farbstoffe eignen sich in hervorragender Weise zum Färben von hydroxylgruppenhaltigen und stickstoffhaltigen natürlichen oder synthetischen Fasermaterialien, beispielsweise Cellulosefasern in allen Verarbeitungszuständen, insbesondere von Baumwolle und Regeneratcellulose, sowie von Wolle, Halbwolle, Seide, Nylon, Leder und'Papier. Man erhält grüne bis schwarze Färbungen mit guten Echtheitseigenschaften, insbesondere guten Wasser- und Schweißechtheiten nach Nachbehandlung mit kationaktiven Hilfsmitteln.The new dyes are outstandingly suitable for dyeing hydroxyl-containing and nitrogen-containing ones natural or synthetic fiber materials, for example cellulose fibers in all processing states, in particular of cotton and regenerated cellulose, as well as wool, semi-wool, silk, nylon, leather and paper. You get green to black Dyeings with good fastness properties, in particular good water and perspiration fastness properties after aftertreatment with cationic active substances Tools.
13,8 Teile l-Amino-4-nitro-benzol werden in üblicher Weise diazotiert. In diese Diazotierung läßt man eine neutrale Lösung von 31,9 Teilen 1-Amino-8-hydroxy-naphthalin-3,6-disulf osäure in 150 ml Wasser einlaufen. Nach Rühren über Nacht13.8 parts of l-amino-4-nitro-benzene are used in the usual way diazotized. A neutral solution of 31.9 parts of 1-amino-8-hydroxynaphthalene-3,6-disulf is allowed into this diazotization run acid in 150 ml of water. After stirring overnight
Le A 13 620 - 4 - Le A 13 620 - 4 -
209838/1 153209838/1 153
ist die Kupplung beendet. Durch Einstreuen von 15 Teilen Natriumcarbonat wird die Kupplung bei pH 7 in Lösung gebracht. Nun werden 22,7 Teile 4-Aminqbenzoyl-4'-aminoanilid in einem Gemisch aus 23 Teilen Wasser und 56 Teilen 30%iger wässriger Salzsäure bei 0-1O0G mit 13,8 Teilen Natriumnitrit tetrazotiert. Nachdem die erste Kupplung mit 20 Teilen Natriumcarbonat versetzt wurde, läuft sie zur vorher mit Natriumcarbonatlösung con-» goneutral gestellten Tetrazotierung des 4-Aminobenzoyl-4'-aminoanilids. Nach ca. 15 Minuten ist die halbseitige Kupplung beendet. Dann gibt man eine Lösung von 9,4 Teilen Phenol in 100 Teilen Wasser und 17 Teilen Natriumcarbonat zu. Die Kupplung rührt über Nacht. Dann wird der Farbstoff mit Steinsalz ausgesalzen, abfiltriert und getrocknet. Der Farbstoff färbt Baumwolle in grünem Ton.the clutch is finished. The coupling is brought into solution at pH 7 by sprinkling in 15 parts of sodium carbonate. 22.7 parts now be 4-Aminqbenzoyl-4'-aminoanilide tetrazotized in a mixture of 23 parts water and 56 parts of 30% aqueous hydrochloric acid at 0-1O 0 G 13.8 parts of sodium nitrite. After the first coupling has been admixed with 20 parts of sodium carbonate, it proceeds to the tetrazotization of 4-aminobenzoyl-4'-aminoanilide, which was previously rendered positively with sodium carbonate solution. The half-sided coupling is completed after approx. 15 minutes. A solution of 9.4 parts of phenol in 100 parts of water and 17 parts of sodium carbonate is then added. The coupling stirs overnight. Then the dye is salted out with rock salt, filtered off and dried. The dye dyes cotton in a green tone.
Weitere Farbstoffe, die erfindungsgemäß hergestellt werden können, sind in der nachfolgenden Tabelle nach Komponenten unter Angabe der Farbtöne zusammengefaßt.Further dyes which can be prepared according to the invention are listed in the table below by component summarized with details of the color shades.
Le A 15 620 - 5- Le A 15 620 - 5-
209838/1153209838/1153
Beisp. A-NH9 Nr.Example A-NH 9 No.
OH NHOH NH
(SO3H)n (SO 3 H) n
Vv-CONH-/' D ^-Vv-CONH- / 'D ^ -
H-B Farbton auf BaumwolleH-B shade on cotton
4-Nitro- l-Amino-8-hydroxyanilin naphthalin-3,6-disulfosäure 4-nitro-1-amino-8-hydroxyaniline naphthalene-3,6-disulfonic acid
4-Aminobenzoyl-4 aminoanilid4-aminobenzoyl-4 aminoanilide
1,3-Diamino·
benzol1,3-diamino
benzene
grünstichig schwarzgreenish black
2-Chloranilin schwarz2-chloroaniline black
Le A 13Le A 13
6 -6 -
Färbebeispiel: Coloring example :
In einem Färbebecher von 500 ml Inhalt, der sich in einem beheizbaren Wasserbad befindet, werden 260 ml Wasser von 50 - 600C vorgelegt und 10 ml lO&Lger Natriumsulfatlösung sowie 1 ml 10%iger Natriumcarbonatlösung zugesetzt. Man teigt 0,25 g Farbstoff mit 2 ml kaltem Wasser gut an und fügt.30 ml warmes Wasser (50 - 60°C) zu; dabei löst sich der Farbstoff auf. Die Farbstofflösung wird der vorgelegten Flotte zugefügt und 10 g Baumwollgewebe in dieser Färbeflotte ständig in Bewegung gehalten. Innerhalb 30 Minuten erhöht man die Temperatur der Färbeflotte auf 85 - 900C und färbt 60 Minuten bei dieser Temperatur weiter. Man entnimmt das gefärbte Material der Färbeflotte, entfernt die anhaftende Flotte durch Auswringen, spült das Material 5-10 Minuten mit kaltem Wasser und trocknet bei 60 - 700C.In a dyeing beaker of 500 ml capacity, which is located in a heated water bath, 260 ml of water at 50 to - 60 0 C and 10 ml submitted lO & Lger sodium sulfate solution and 1 ml of 10% sodium carbonate solution added. Mix 0.25 g of dye with 2 ml of cold water and add 30 ml of warm water (50 - 60 ° C); the dye dissolves in the process. The dye solution is added to the liquor and 10 g of cotton fabric is kept in constant motion in this dye liquor. Within 30 minutes, increasing the temperature of the dye bath at 85 to 90 0 C and dyed for 60 minutes at this temperature further. It removes the colored material of the dyeing liquor, removed the adhering liquor by wringing, the material flushed 5-10 minutes with cold water and dried at 60-70 0 C.
Le A 13 620 - 7 - Le A 13 620 - 7 -
209838/1163209838/1163
Claims (1)
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19712110771 DE2110771C3 (en) | 1971-03-06 | 1971-03-06 | Trisazo dyes and their use for dyeing hydroxyl-containing and nitrogen-containing fiber materials |
GB1030572A GB1327914A (en) | 1971-03-06 | 1972-03-02 | Trisazo dyestuffs |
JP2163472A JPS544975B1 (en) | 1971-03-06 | 1972-03-03 | |
CH165574A CH549081A (en) | 1971-03-06 | 1972-03-03 | PROCESS FOR THE MANUFACTURING OF TRISAZO DYES. |
NL7202869A NL7202869A (en) | 1971-03-06 | 1972-03-03 | |
CH317072A CH555443A (en) | 1971-03-06 | 1972-03-03 | |
IT2145172A IT953444B (en) | 1971-03-06 | 1972-03-04 | TRISAZOCOLORANTS |
BE780255A BE780255A (en) | 1971-03-06 | 1972-03-06 | TRISAZOIC DYES |
FR7207688A FR2128658B1 (en) | 1971-03-06 | 1972-03-06 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19712110771 DE2110771C3 (en) | 1971-03-06 | 1971-03-06 | Trisazo dyes and their use for dyeing hydroxyl-containing and nitrogen-containing fiber materials |
Publications (3)
Publication Number | Publication Date |
---|---|
DE2110771A1 true DE2110771A1 (en) | 1972-09-14 |
DE2110771B2 DE2110771B2 (en) | 1979-08-30 |
DE2110771C3 DE2110771C3 (en) | 1980-05-14 |
Family
ID=5800734
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19712110771 Expired DE2110771C3 (en) | 1971-03-06 | 1971-03-06 | Trisazo dyes and their use for dyeing hydroxyl-containing and nitrogen-containing fiber materials |
Country Status (8)
Country | Link |
---|---|
JP (1) | JPS544975B1 (en) |
BE (1) | BE780255A (en) |
CH (2) | CH555443A (en) |
DE (1) | DE2110771C3 (en) |
FR (1) | FR2128658B1 (en) |
GB (1) | GB1327914A (en) |
IT (1) | IT953444B (en) |
NL (1) | NL7202869A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2306768A1 (en) * | 1972-02-15 | 1973-08-23 | Sandoz Ag | POLYAZO COMPOUNDS, THEIR MANUFACTURING AND USE |
US4479906A (en) * | 1972-11-09 | 1984-10-30 | Basf Aktiengesellschaft | Trisazo dye |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5180817A (en) * | 1990-03-28 | 1993-01-19 | Sumitomo Chemical Company, Limited | Trisazo compounds and use thereof |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB338111A (en) * | 1929-07-03 | 1930-11-03 | Ici Ltd | Improvements in the dyeing of regenerated cellulose materials |
FR892914A (en) * | 1940-10-10 | 1944-05-24 | Ig Farbenindustrie Ag | Process for the production of asymmetric polyazo dyes |
FR1100541A (en) * | 1954-05-11 | 1955-09-21 | Hoechst Ag | Poly-azo dyes and process for the preparation of these dyes |
-
1971
- 1971-03-06 DE DE19712110771 patent/DE2110771C3/en not_active Expired
-
1972
- 1972-03-02 GB GB1030572A patent/GB1327914A/en not_active Expired
- 1972-03-03 JP JP2163472A patent/JPS544975B1/ja active Pending
- 1972-03-03 CH CH317072A patent/CH555443A/xx unknown
- 1972-03-03 CH CH165574A patent/CH549081A/en not_active IP Right Cessation
- 1972-03-03 NL NL7202869A patent/NL7202869A/xx unknown
- 1972-03-04 IT IT2145172A patent/IT953444B/en active
- 1972-03-06 FR FR7207688A patent/FR2128658B1/fr not_active Expired
- 1972-03-06 BE BE780255A patent/BE780255A/en unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2306768A1 (en) * | 1972-02-15 | 1973-08-23 | Sandoz Ag | POLYAZO COMPOUNDS, THEIR MANUFACTURING AND USE |
US4479906A (en) * | 1972-11-09 | 1984-10-30 | Basf Aktiengesellschaft | Trisazo dye |
Also Published As
Publication number | Publication date |
---|---|
DE2110771C3 (en) | 1980-05-14 |
CH549081A (en) | 1974-05-15 |
FR2128658B1 (en) | 1976-06-11 |
NL7202869A (en) | 1972-09-08 |
CH555443A (en) | 1974-10-31 |
FR2128658A1 (en) | 1972-10-20 |
GB1327914A (en) | 1973-08-22 |
JPS544975B1 (en) | 1979-03-12 |
BE780255A (en) | 1972-09-06 |
DE2110771B2 (en) | 1979-08-30 |
IT953444B (en) | 1973-08-10 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
OD | Request for examination | ||
C3 | Grant after two publication steps (3rd publication) | ||
8339 | Ceased/non-payment of the annual fee |