CH493598A - Blue azo dyestuffs for polyester and cellulose acetate - Google Patents
Blue azo dyestuffs for polyester and cellulose acetateInfo
- Publication number
- CH493598A CH493598A CH535468A CH535468A CH493598A CH 493598 A CH493598 A CH 493598A CH 535468 A CH535468 A CH 535468A CH 535468 A CH535468 A CH 535468A CH 493598 A CH493598 A CH 493598A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- blue
- polyester
- formula
- azo dyestuffs
- Prior art date
Links
- 229920000728 polyester Polymers 0.000 title description 4
- 229920002301 cellulose acetate Polymers 0.000 title 1
- -1 polyethylene terephthalate Polymers 0.000 claims abstract description 6
- 230000008878 coupling Effects 0.000 claims abstract description 5
- 238000010168 coupling process Methods 0.000 claims abstract description 5
- 238000005859 coupling reaction Methods 0.000 claims abstract description 5
- 239000000987 azo dye Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 abstract description 7
- 239000000463 material Substances 0.000 abstract description 5
- 229920000139 polyethylene terephthalate Polymers 0.000 abstract description 4
- 239000005020 polyethylene terephthalate Substances 0.000 abstract description 4
- 238000009835 boiling Methods 0.000 abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 3
- 229920002284 Cellulose triacetate Polymers 0.000 abstract description 2
- 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 abstract description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract description 2
- 230000002209 hydrophobic effect Effects 0.000 abstract description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000002657 fibrous material Substances 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-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
- 238000003756 stirring Methods 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-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
- 239000005711 Benzoic acid Substances 0.000 description 1
- 206010011416 Croup infectious Diseases 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 229920006221 acetate fiber Polymers 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- IILAFGOJFGBAGC-UHFFFAOYSA-N n-bromo-2,4-dinitroaniline Chemical compound [O-][N+](=O)C1=CC=C(NBr)C([N+]([O-])=O)=C1 IILAFGOJFGBAGC-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 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
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920006304 triacetate fiber Polymers 0.000 description 1
- 238000005406 washing Methods 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
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
-
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
Azo dyestuffs (I) X = Cl or Br; R1 and R2 = methyl or ethyl; and R3 = C1-6 alkyl. (I) are prepd. by coupling a diazo component (II) with (iii). In a pref. cpd. (I), X = Br; R1 and R2 = CH3; and R3 = C2H5. (I) are useful for dyeing hydrophobic material, esp. fibres composed of polyethylene terephthalate or cellulose triacetate. The dyestuffs show a high colour intensity in shades of blue. The dyed goods have high fastness, esp. fastness to boiling.
Description
Verfahren zur Herstellung von Azofarbstoffen
Es wurde gefunden, dass man wertvolle blaue Azofarbstoffe erhält, wenn man ein diazotiertes Amin der Formel
EMI1.1
in welcher X für C1 oder Br steht, Init einer Krupp lungskomponente der Formel
EMI1.2
in welcher Rt und Rp für CH8 oder C2H stehen und Rs einen Alkylrest mit 1 4 C-Atomen darstellt, in p-Stellung zur Aminogruppe vereinigt.
Die Kupplung kann in üblicher Weise erfolgen, vorzugsweise in saurer Lösung oder Suspension.
Unter den erfindungsgemäss erhältlichen Farbstoffen der Formel
EMI1.3
sind solche bevorzugt, in denen Rt und R2 für CH" und Rs für C2Hs steht. Besonders bevorzugt in dieser Reihe sind solche Farbstoffe, in denen X für Br steht.
Die erfindungsgemäss erhältlichen Farbstoffe der Formel (I) eignen sich vorzüglich zum Färben und Bedrucken hydrophober Materialien, wie Textilien oder Fasern aus aromatischen Polyestern, wie Polyäthylenterephthalat oder Kondensationsprodukten aus Terephthalsäure und 1 ,4-Bis-(hydroxymethyl)-cyclohexan oder Cellulosetriacetat. Man erhält auf diesen Materialien Färbungen und Drucke von sehr guten Echtheits- eigenschaften, insbesondere guter Verkochechtheit. Die Farbstoffe zeichnen sich ausserdem durch besonders hohe Farbstärke aus.
Das Färben mit den Farbstoffen der Formel (I) wird z. B. im einzelnen derart durchgeführt, dass man das zu färbende Material, vorzugsweise bei erhöhter Temperatur (z. B. bei 400 C) in eine wässrige Dispersion der Farbstoffe einbringt, gegebenenfalls übliche Hilfsmittel, wie Sulfitcellulose-Abbauprodukte, Kondensationsprodukte aus höheren Alkoholen mit Athylenoxyd, Polyglykoläther von Fettsäureamiden oder Alkylphenolen, Sulfobernsteinsäureester oder Türkischrotöl, zusetzt und das Bad vorzugsweise mit sauren Mitteln versetzt, beispielsweise mit organischen Säuren, wie Ameisensäure oder Essigsäure, oder anorganischen Säuren, wie Phosphorsäure.
Das Bad wird dann auf die optimale Färbetemperatur erhitzt, vorzugsweise und je nach Art der zu färbenden Fasermaterialien auf eine Temperatur zwi schen 70" und 1400 C. Bei dieser Temperatur wird bis zum Erreichen der gewünschten Farbtiefe gefärbt. Nach Abkühlen des Bades kann das gefärbte Fasermaterial einer Nachbehandlung unterzogen werden, z. B. im Falle von Acetatfasern einer Nachbehandlung mit Seifen, oder im Falle von Fasern aus aromatischen Polyestern einer reduktiven Nachbehandlung unter Alkalizusatz.
Beim Färben von aromatischen Polyestern oder Triacetatfasern bei Temperaturen bis 1050 C ist es im allgemeinen vorteilhaft, übliche Carriersubstanzen mitzuverwenden, wie Mono-, Di- oder Trichlorbenzol, Benzoesäure, Salicylsäure, Salicylsäuremethylester, Kresotinsäuremethylester, o- oder p-Phenylphenol, ss-Naphthylthyläther oder Benzylalkohol.
Das Bedrucken kann gleichfalls in an sich bekannter Weise durchgeführt werden, indem man auf die Materialien eine Druckpaste aufbringt, weiche neben üblichen Hilfsmitteln den oder die Farbstoffe enthält, und anschliessend einer Wärme- bzw. Hitzebehandlung unterwirft.
Beispiel
26,2 G 2,4-Dinitrobromanilin werden in 200 g konzentrierter Schwefelsäure gelöst und durch Zugabe von 17 ml Nitrosylschwefelsäure (100 ml entsprechen 42 g Nitrit) unter Rühren bei 0-5" C diazotiert. Die Dia zoiniumsalzlösung wird unter Rühren in eine Lösung von 26,1 g der Verbindung der Formel
EMI2.1
in verdünnter Schwefelsäure und Eis eingegossen. Dann wird zunächst mit Natronlauge und schliesslich mit Natriumacetat auf pH 5,5-6 abgestumpft, abgesaugt, gewaschen und getrocknet.
Der entstandene Farbstoff ist ein schwarzes Pulver, das sich in organischen Lösungsmitteln mit blauer Farbe löst. Durch geeignete Mittel in feine Verteilung gebracht, färbt der Farbstoff Polyäthylenterephthalatfasern in blauen Farbtönen mit guter Sublimier-, Wasch-, Licht- und Verkochechtheit.
In analoger Weise erhält man aus den entsprechenden Diazo- und Kupplungskomponenten die folgenden Farbstoffe, die Polyäthylenterephthalatgewebe in den angegebenen Farbtönen färben:
EMI3.1
<tb> <SEP> CL <SEP> OCH3
<tb> <SEP> C2H5
<tb> 02N- <SEP> -N=N-C,Hg <SEP> C2H4CN <SEP> blau
<tb> <SEP> blau
<tb> <SEP> Br <SEP> OC2H5
<tb> <SEP> -N <SEP> C2H5
<tb> 02N- <SEP> /\-N=N- <SEP> C2H5CN <SEP> blau
<tb> <SEP> 2 <SEP> NHCOCH3
<tb> <SEP> C1 <SEP> C2H5
<tb> 02N- <SEP> -N=N- <SEP> ss <SEP> N <SEP> C2H5 <SEP> blau
<tb> <SEP> - <SEP> - <SEP> 2H4CN
<tb> <SEP> NO2 <SEP> NHCOCH)
<tb> <SEP> Br <SEP> OCH3
<tb> O <SEP> N- <SEP> 4 <SEP> -N=N- <SEP> ss <SEP> -N <SEP> C2H4CN <SEP> blau
<tb> <SEP> N02 <SEP> NHCOC2H5
<tb> <SEP> Br <SEP> OCH3
<tb> <SEP> -N=N-/ <SEP> C5H7
<tb> 02N- <SEP> Q <SEP> -N=N- <SEP> ss <SEP> -N <SEP> / <SEP> 3 <SEP> 7 <SEP> blau
<tb> <SEP> NO2 <SEP> NHCOCH3
<tb>
<SEP> C1 <SEP> OCH3
<tb> 02N- <SEP> NÜCC32)CN <SEP> blau
<tb> <SEP> NO2 <SEP> NHCOCH3
<tb> <SEP> Br <SEP> NOCH,
<tb> <SEP> C4H9
<tb> 02N- <SEP> X <SEP> -N=N- <SEP> ss <SEP> C21I4CN <SEP> blau
<tb> <SEP> NO2 <SEP> NHCOCH3
<tb>
Process for the production of azo dyes
It has been found that valuable blue azo dyes are obtained when using a diazotized amine of the formula
EMI1.1
in which X stands for C1 or Br, Init a Krupp treatment component of the formula
EMI1.2
in which Rt and Rp stand for CH8 or C2H and Rs represents an alkyl radical with 14 C atoms, combined in the p-position to the amino group.
The coupling can be carried out in the usual way, preferably in acidic solution or suspension.
Among the dyes of the formula obtainable according to the invention
EMI1.3
those in which Rt and R2 are CH ″ and Rs are C2Hs are preferred. Particularly preferred in this series are those dyes in which X is Br.
The dyes of the formula (I) obtainable according to the invention are particularly suitable for dyeing and printing hydrophobic materials, such as textiles or fibers made from aromatic polyesters such as polyethylene terephthalate or condensation products from terephthalic acid and 1,4-bis (hydroxymethyl) cyclohexane or cellulose triacetate. On these materials, dyeings and prints with very good fastness properties, in particular good boiling fastness, are obtained. The dyes are also characterized by particularly high color strength.
The dyeing with the dyes of formula (I) is z. B. carried out in such a way that the material to be colored, preferably at elevated temperature (z. B. at 400 C) is introduced into an aqueous dispersion of the dyes, optionally customary auxiliaries, such as sulfite cellulose degradation products, condensation products of higher alcohols with ethylene oxide , Polyglycol ethers of fatty acid amides or alkylphenols, sulfosuccinic acid esters or Turkish red oil, and the bath is preferably mixed with acidic agents, for example with organic acids such as formic acid or acetic acid, or inorganic acids such as phosphoric acid.
The bath is then heated to the optimal dyeing temperature, preferably and depending on the type of fiber material to be dyed to a temperature between 70 "and 1400 C. At this temperature, the dyeing is carried out until the desired depth of color is achieved. After the bath has cooled down, the dyed fiber material be subjected to an aftertreatment, e.g. in the case of acetate fibers, an aftertreatment with soaps, or in the case of fibers made of aromatic polyesters, a reductive aftertreatment with the addition of alkali.
When dyeing aromatic polyesters or triacetate fibers at temperatures up to 1050 ° C., it is generally advantageous to use customary carrier substances such as mono-, di- or trichlorobenzene, benzoic acid, salicylic acid, methyl salicylate, methyl cresotinate, o- or p-phenylphenol, or sthyl-naphthyl Benzyl alcohol.
Printing can also be carried out in a manner known per se by applying a printing paste to the materials which, in addition to customary auxiliaries, contains the dye or dyes, and then subjecting it to a heat or heat treatment.
example
26.2 g of 2,4-dinitrobromaniline are dissolved in 200 g of concentrated sulfuric acid and diazotized by adding 17 ml of nitrosylsulfuric acid (100 ml corresponds to 42 g of nitrite) with stirring at 0-5 ° C. The diazonium salt solution is converted into a solution with stirring of 26.1 g of the compound of formula
EMI2.1
poured in dilute sulfuric acid and ice. Then it is first blunted with sodium hydroxide solution and finally with sodium acetate to pH 5.5-6, filtered off with suction, washed and dried.
The resulting dye is a black powder that dissolves in organic solvents with a blue color. Finely divided by suitable means, the dye dyes polyethylene terephthalate fibers in blue shades with good fastness to sublimation, washing, light and boiling.
In an analogous manner, the following dyes are obtained from the corresponding diazo and coupling components, which dye polyethylene terephthalate fabrics in the specified shades:
EMI3.1
<tb> <SEP> CL <SEP> OCH3
<tb> <SEP> C2H5
<tb> 02N- <SEP> -N = N-C, Hg <SEP> C2H4CN <SEP> blue
<tb> <SEP> blue
<tb> <SEP> Br <SEP> OC2H5
<tb> <SEP> -N <SEP> C2H5
<tb> 02N- <SEP> / \ - N = N- <SEP> C2H5CN <SEP> blue
<tb> <SEP> 2 <SEP> NHCOCH3
<tb> <SEP> C1 <SEP> C2H5
<tb> 02N- <SEP> -N = N- <SEP> ss <SEP> N <SEP> C2H5 <SEP> blue
<tb> <SEP> - <SEP> - <SEP> 2H4CN
<tb> <SEP> NO2 <SEP> NHCOCH)
<tb> <SEP> Br <SEP> OCH3
<tb> O <SEP> N- <SEP> 4 <SEP> -N = N- <SEP> ss <SEP> -N <SEP> C2H4CN <SEP> blue
<tb> <SEP> N02 <SEP> NHCOC2H5
<tb> <SEP> Br <SEP> OCH3
<tb> <SEP> -N = N- / <SEP> C5H7
<tb> 02N- <SEP> Q <SEP> -N = N- <SEP> ss <SEP> -N <SEP> / <SEP> 3 <SEP> 7 <SEP> blue
<tb> <SEP> NO2 <SEP> NHCOCH3
<tb>
<SEP> C1 <SEP> OCH3
<tb> 02N- <SEP> NÜCC32) CN <SEP> blue
<tb> <SEP> NO2 <SEP> NHCOCH3
<tb> <SEP> Br <SEP> STILL,
<tb> <SEP> C4H9
<tb> 02N- <SEP> X <SEP> -N = N- <SEP> ss <SEP> C21I4CN <SEP> blue
<tb> <SEP> NO2 <SEP> NHCOCH3
<tb>
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0052365 | 1967-05-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH493598A true CH493598A (en) | 1970-07-15 |
Family
ID=7105390
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH535468A CH493598A (en) | 1967-05-09 | 1968-04-10 | Blue azo dyestuffs for polyester and cellulose acetate |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE714848A (en) |
| CH (1) | CH493598A (en) |
| DE (1) | DE1644209C3 (en) |
| FR (1) | FR1563458A (en) |
| GB (1) | GB1152317A (en) |
| NL (1) | NL6806594A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH633307A5 (en) * | 1977-03-16 | 1982-11-30 | Ciba Geigy Ag | AZO DYES. |
| JPH09249818A (en) * | 1996-03-19 | 1997-09-22 | Nippon Kayaku Co Ltd | Heat-stable crystalline modification of dye, its production and dyeing of hydrophobic fiber using the same |
-
1967
- 1967-05-09 DE DE1644209A patent/DE1644209C3/en not_active Expired
-
1968
- 1968-04-10 CH CH535468A patent/CH493598A/en not_active IP Right Cessation
- 1968-05-01 GB GB2059868A patent/GB1152317A/en not_active Expired
- 1968-05-08 BE BE714848D patent/BE714848A/xx unknown
- 1968-05-09 NL NL6806594A patent/NL6806594A/xx unknown
- 1968-05-09 FR FR1563458D patent/FR1563458A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1563458A (en) | 1969-04-11 |
| DE1644209B2 (en) | 1974-08-22 |
| DE1644209A1 (en) | 1970-12-17 |
| NL6806594A (en) | 1968-11-11 |
| GB1152317A (en) | 1969-05-14 |
| BE714848A (en) | 1968-09-30 |
| DE1644209C3 (en) | 1975-04-24 |
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