DE386054C - Process for the preparation of water-insoluble azo dyes - Google Patents
Process for the preparation of water-insoluble azo dyesInfo
- Publication number
- DE386054C DE386054C DEC31468D DEC0031468D DE386054C DE 386054 C DE386054 C DE 386054C DE C31468 D DEC31468 D DE C31468D DE C0031468 D DEC0031468 D DE C0031468D DE 386054 C DE386054 C DE 386054C
- Authority
- DE
- Germany
- Prior art keywords
- yellow
- orange
- water
- chloro
- toluidine
- 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
- 239000000987 azo dye Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title description 7
- 150000008049 diazo compounds Chemical class 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- 239000000975 dye Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 244000248349 Citrus limon Species 0.000 description 8
- 235000005979 Citrus limon Nutrition 0.000 description 8
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 5
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
- PBGKNXWGYQPUJK-UHFFFAOYSA-N 4-chloro-2-nitroaniline Chemical compound NC1=CC=C(Cl)C=C1[N+]([O-])=O PBGKNXWGYQPUJK-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 4
- PFRYFZZSECNQOL-UHFFFAOYSA-N 2-methyl-4-[(2-methylphenyl)diazenyl]aniline Chemical compound C1=C(N)C(C)=CC(N=NC=2C(=CC=CC=2)C)=C1 PFRYFZZSECNQOL-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- GOJFAKBEASOYNM-UHFFFAOYSA-N 2-(2-aminophenoxy)aniline Chemical compound NC1=CC=CC=C1OC1=CC=CC=C1N GOJFAKBEASOYNM-UHFFFAOYSA-N 0.000 description 1
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 description 1
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- PZDXDOLQKQBWJV-UHFFFAOYSA-N 4-(nitromethoxy)aniline Chemical class NC1=CC=C(OC[N+]([O-])=O)C=C1 PZDXDOLQKQBWJV-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- BVPJPRYNQHAOPQ-UHFFFAOYSA-N 4-nitronaphthalen-1-amine Chemical compound C1=CC=C2C(N)=CC=C([N+]([O-])=O)C2=C1 BVPJPRYNQHAOPQ-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- -1 aminoazo compounds Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- DADSZOFTIIETSV-UHFFFAOYSA-N n,n-dichloroaniline Chemical compound ClN(Cl)C1=CC=CC=C1 DADSZOFTIIETSV-UHFFFAOYSA-N 0.000 description 1
- QFCSRGLEMDRBMN-UHFFFAOYSA-N n-(2-methylphenyl)nitramide Chemical class CC1=CC=CC=C1N[N+]([O-])=O QFCSRGLEMDRBMN-UHFFFAOYSA-N 0.000 description 1
- CHMBIJAOCISYEW-UHFFFAOYSA-N n-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- 150000005002 naphthylamines Chemical class 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 239000002966 varnish 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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
- C09B33/153—Disazo dyes in which the coupling component is a bis-(aceto-acetyl amide) or a bis-(benzoyl-acetylamide)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellunu von wasserunlöslichen Azofarbstoffen. Es wurde gefunden, daß bei der Kombination solcher Diazoverbindungen, welche keine Sulfo- oder Carboxylgruppe enthalten; mit Diacetessigsäurearyliden der allgemeinen Formel: CH3.CO.CH2.CO.NH.X.NH. CO.CH..CO-CH3, worin X einen gegebenenfalls substituierten Diphenylrest bedeutet, wasserunlösliche Azofarbstoffe entstehen, welche- durch besonders wertvolle Eigenschaften ausgezeichnet sind.Process for the preparation of water-insoluble azo dyes. It it was found that when combining such diazo compounds, which none Contain sulfo or carboxyl group; with diacetoacetic acid arylides of the general Formula: CH3.CO.CH2.CO.NH.X.NH. CO.CH..CO-CH3, where X is an optionally substituted one Diphenyl radical means, water-insoluble azo dyes are formed, which are particularly valuable properties are excellent.
Azofarbstoffe aus Diacetessigsäurearyliden sind bisher nicht bekannt geworden.Azo dyes made from diacetoacetic acid arylides are not yet known become.
Sehr bemerkenswert ist es im Hinblick auf die bisherigen Veröffentlichungen über Farbstoffe aus Acetessigaryliden. .daß nicht nur die Kombinationen von Nitrodiazoverbindungen mit den Diacetessigsäurearyliden brauchbare Produkte liefern, sondern daß auch Diazoverbindungen von chlorsubstituierten Anilinen u. dgl. und sogar von Anilin und dessen Homologen selbst mit Diacetessigsäurearyliden genügend farbstarke Pigmente ergeben.It is very noteworthy in view of the publications so far about dyes from acetoacetic arylides. .that not only the combinations of nitrodiazo compounds with the diacetoacetic acid arylides provide useful products, but also diazo compounds of chlorine substituted anilines and the like, and even of aniline and its homologues Even with diacetoacetic acid arylides, pigments of sufficient color strength can be obtained.
Besonders überraschend und technisch wichtig ist die Erkenntnis, daß die Diacetessigsäurearylide: eine.gewisse Affinität zur Baumwolle haben, die es ermöglicht, die Farbstoffe in der Weise auf der Faser zu erzeugen, daß man das Gut mit der alkalischen Lösung eines Diacetessi.gsäurearylides klotzt und nach dem Abquetschen, ohne zu trocknen, mit Diazovenbindungen entwickelt. Die so erhaltenen Färbungen sind völlig waschecht, sie zeigen eine gute, zum Teil hervorragende Lichtbeständigkeit und vorzügliche Chlorechtheit. Mit Hilfe- der bekannten Kombinationen mit Acetessigaryliden war es bisher nicht möglich, genügend farbstarke, technisch brauchbare Färbungen auf Baumwollgarn im Eisfarbenverfahren zu erzeugen.Particularly surprising and technically important is the realization that the diacetoacetic acid arylides: have a certain affinity for cotton, which it makes it possible to produce the dyes on the fiber in such a way that the material can be used puddles with the alkaline solution of a diacetessi.gsäurearylides and after squeezing, Developed without drying, with diazo bonds. The dyeings thus obtained are completely washable, they show good, in some cases excellent lightfastness and excellent chlorine fastness. With the help of the known combinations with acetoacetic arylides it was not previously possible to obtain technically useful dyeings of sufficient strength to produce on cotton yarn using the ice color process.
Mit den in der Farblackfalbrikation üblichen Substraten gemischt, geben die neuen Farbstoffe wertvolle Pigmente, deren Ölechtheit von der Art der Substituenten im Diazo- oder Arylidrest abhängig ist.Mixed with the substrates commonly used in paint varnish, give the new dyes valuable pigments, whose oilyness depends on the nature of the Substituents in the diazo or arylide radical is dependent.
Als Diazoverbindungen kommen in dem Verfahren z. B. die aus Anilin und seinen Homologen und Sibstitutionsprodukten, wie Toluidine, Anisidine, Chlor- und Nitroaniline, Chlor- und Nitrotoluidine, Chlor- und Nitroanisidine, ferner solche aus Naphthylaminen, Aminoanthrachinonen, Aminoazoverbindungen, Diaminobasen usw. in Betracht, als Azokomponenten finden das Diacetessigsäurebenzidinid selbst sowie seine im Diphenylrest substituierten Derivate Verwendung.As diazo compounds come in the process, for. B. those made of aniline and its homologues and sibstitution products, such as toluidines, anisidines, chlorine and nitroanilines, chloro- and nitrotoluidines, chloro- and nitroanisidines, and also those from naphthylamines, aminoanthraquinones, aminoazo compounds, diamino bases, etc. considered as Azo components find the diacetoacetic acid benzidinide itself as well as its derivatives substituted in the diphenyl radical use.
Das Diacetessigsäurebenzidinid kann nach H e i d r i c h , Monatshefte der Chemie 19, S. 69d., dargestellt werden. Die neuen, ,bisher noch nicht beschriebenen Substitutionsprodukte können in ähnlicher Weise durch Erhitzen der entsprechenden Diaminodiphenvlbasen mit Acetessigester gewonnen werden.The Diacetessigsäurebenzidinid can according H eidrich, are represented Monatshefte der Chemie 1 9, pp 69d.. The new, so far not yet described substitution products can be obtained in a similar manner by heating the corresponding diaminodiphenyl bases with acetoacetic ester.
Das Diacetessigsäure-o-tolidinid kristallisiert aus Sprit in feinen, glänzenden Nädelchen,welche bei 2o4 bis 2o5° (unkorr.) unter Zersetzung schmelzen. Es ist löslich in Sprit. Eisessig und Nitrobenzol, weniger in Aceton und Essigester, unlöslich in Benzol, Äther und Tetrachlorkohlenstoff.The diacetoacetic acid-o-tolidinide crystallizes from fuel in fine, shiny needles which melt at 2o4 to 2o5 ° (uncorrected) with decomposition. It is soluble in fuel. Glacial acetic acid and nitrobenzene, less in acetone and ethyl acetate, insoluble in benzene, ether and carbon tetrachloride.
Das Diacetessigsäure-o - oi-dichlorbenzidinid kommt aus verdünntem Sprit in farblosen Flocken heraus und zeigt den Zersetzungspunkt 145 bis 147' (unkorr.). Es ist löslich in Sprit, Eisessig, Aceton und Nitrobenzol, weniger in Benzol. unlöslich in _3ther und Tetrachlorkohlenstoff.The diacetoacetic acid-o-oi-dichlorobenzidinide comes from dilute Fuel comes out in colorless flakes and shows the decomposition point 145 to 147 '(uncorrupted). It is soluble in gasoline, glacial acetic acid, acetone and nitrobenzene, less so in benzene. insoluble in _3ther and carbon tetrachloride.
Das Diacetessigsäuredianisidini(l bildet aus Sprit feine, schwach gelbliche Nädelchen, welche bei 164 bis i65° (unkorr.) unter Zersetzung schmelzen. Es ist löslich in Sprit, Eisessig und Nitrobenzol, weniger in Benz-)l, unlöslich dagegen in Äther und Tetrachlorkohlenstoff.The diacetoacetic acid dianisidini (l turns fuel into fine, weak yellowish needles, which melt at 164 to 165 ° (uncorrupted) with decomposition. It is soluble in petrol, glacial acetic acid and nitrobenzene, and less so in benzene, insoluble on the other hand in ether and carbon tetrachloride.
Alle diese Diacetessigsäurearylide lösen sich leicht in verdünnter Natronlauge. Beispiel i. 32,4 Teile 2 - 5-Dichloranilin werden in der üblichen Weise diazotiert, und die Diazolösung mit einer Lösung von 4o Teilen Diacetessigsäure-o-tolidinid in wäßrigem Alkali, welche mit der nötigen Menge Natriumacetat versetzt ist, zusammengegeben. Nach beendeter Kupplung wird der Farbstoff abfiltriert, gut gewaschen und zur Paste verrieben. Mit den gebräuchlichen Substraten gemischt, bildet er einen rotstichig gelben Lack von sehr guten Echtheitseigenschaften. Beispiel 2. Herstellung der Farbstoffe auf der Faser. Grun.di erungsbad ioo g Diacetessigsäure-o-tolidinid werden mit i5o ccm Natronlauge 34° B6 und Zoo ccm Türkischrotöl angerührt, durch Zugabe von i 1 kochendem Wasser in Lösung gebracht und mit kaltem Wasser auf io 1 eingestellt.All these diacetoacetic acid arylides easily dissolve in dilute ones Caustic soda. Example i. 32.4 parts of 2-5 dichloroaniline are used in the usual way diazotized, and the diazo solution with a solution of 40 parts of diacetoacetic acid-o-tolidinide in aqueous alkali, which is mixed with the necessary amount of sodium acetate, combined. After the coupling has ended, the dye is filtered off, washed well and made into a paste rubbed in. Mixed with the common substrates, it forms a reddish tinge yellow lacquer with very good fastness properties. Example 2. Preparation of the dyes on the fiber. Grunddi erungsbad 100 g of diacetoacetic acid-o-tolidinide are mixed with i5o ccm caustic soda 34 ° B6 and zoo ccm Turkish red oil, mixed by adding i 1 brought into solution in boiling water and adjusted to io 1 with cold water.
Man zieht das gut ausgekochte und getrock-Färbebad. Herstellung der Diazolösungen. i. 5-Chlor-i-2-toluidin.The well-boiled and dry dye bath is drawn out. Making the Diazo solutions. i. 5-chloro-i-2-toluidine.
28 g der Base werden mit 6o cctn Salzsäure von 20° Be und 8oo ccm heißem Wasser gelöst und die Lösung unter Rühren auf Eis gegossen. Sodann wird .bei etwa io° C schnell mit einer Lösung von 15 g Natriumnitrit in 5o ccm Wasser versetzt. Die Diazotierung ist sehr bald beendet. Mit kaltem Wasser wird auf io 1 aufgefüllt. 2. o-Chloranilin. 26 g der Base werden finit 6o ccm Salzsäure 20° Be und 300 ccm Wasser gelöst, die Lösung mit Eis auf 5° abgekühlt und eine Lösung von 15 g Natriumnitrit in 50 ccm Wasser zugegeben. Nach beendeter Diazotierung wird auf io 1 aufgefüllt. 3. o-Nitroanilin.28 g of the base are dissolved with 60 cc hydrochloric acid at 20 ° Be and 8oo cc hot water and the solution is poured onto ice with stirring. Then, .for about offset io ° C rapidly with a solution of 1 5 g of sodium nitrite in 5o cc of water. The diazotization will end very soon. It is made up to io 1 with cold water. 2. o-chloroaniline. 26 g of the base are finely dissolved 60 cc hydrochloric acid 20 ° Be and 300 cc water, the solution is cooled to 5 ° with ice and a solution of 15 g sodium nitrite in 50 cc water is added. After the end of the diazotization, the mixture is made up to io 1. 3. o-nitroaniline.
28g der Base werden mit 4o ccm kaltem Wasser gut angeteigt und 15 g Natriumnitrit zugegeben. Nach vollständiger Lösung des Nitrits trägt man die Paste portionsweise in ein Gemisch von 8oo ccm Wasser, ioo g Eis und 6o ccm Salzsäure 2o° B6 unter gutem Rühren ein, läßt einige Zeit unter öfterem Umrühren stehen, bis die Diazotierung beendet ist, und verdünnt mit kaltem Wasser auf io 1.28g of the base are made into a paste with 40 ccm of cold water and 15 g sodium nitrite added. After the nitrite has completely dissolved, the paste is applied In portions in a mixture of 800 cc water, 100 g ice and 60 cc hydrochloric acid 20 ° B6 with thorough stirring, lets stand for a while, stirring frequently, until the diazotization is complete, and diluted to io 1 with cold water.
Vor dem Gebrauch werden die Diazolösungen mit essigsaurem Natron neutralisiert. Das grundierte und gut abgewundene Garn zieht man einige Minuten in dem Färbebade um, spült einige Male kalt, seift kochend, spült abermals und trocknet.Before use, the diazo solutions are neutralized with sodium acetate. The primed and well wound yarn is left in the dye bath for a few minutes um, rinsed cold a few times, soaped at the boil, rinsed again and dries.
Man erhält so mit 5-Chlor-i - 2-toluidin grünstichig gelbe, mit o-Chloranilin zitronengelbe und mit o-Nitroanilin orangegelbe Färbungen von außerordentlicher Brillanz und guten Echtheitseigenschaften.This gives a greenish-tinged yellow with 5-chloro-i-2-toluidine and yellow with o-chloroaniline lemon-yellow and with o-nitroaniline orange-yellow colorations of extraordinary color Brilliance and good fastness properties.
Die neuen Farbstoffe können auch durch Aufdrucken einer Diazolösung auf grundierte Ware nach der üblichen Arbeitsweise sowie im Nitrosamindruckverfahren erzeugt werden.The new dyes can also be obtained by printing a diazo solution on primed goods according to the usual working method as well as in the nitrosa printing process be generated.
In der nachfolgenden Tabelle sind die Nuancen einer Anzahl nach dem
vorliegenden Verfahren hergestellter Farbstoffe bzw. der daraus erhältlichen Farblacke
angegeben: nete Garn einige Minuten in dieser Lösung um, windet gründlich ab und
entwickelt das nasse Garn in dem nachfolgend .beschriebenen Färbebade.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC31468D DE386054C (en) | 1921-12-14 | 1921-12-14 | Process for the preparation of water-insoluble azo dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC31468D DE386054C (en) | 1921-12-14 | 1921-12-14 | Process for the preparation of water-insoluble azo dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE386054C true DE386054C (en) | 1923-12-01 |
Family
ID=7019835
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC31468D Expired DE386054C (en) | 1921-12-14 | 1921-12-14 | Process for the preparation of water-insoluble azo dyes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE386054C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE928724C (en) * | 1948-12-07 | 1955-06-10 | Ciba Geigy | Process for the preparation of insoluble azo dyes |
| FR2232576A1 (en) * | 1973-06-08 | 1975-01-03 | Hoechst Ag | |
| US5266110A (en) * | 1991-11-01 | 1993-11-30 | Hoechst Aktiengesellschaft | Crystal modification of C.I. Pigment Yellow 16 |
-
1921
- 1921-12-14 DE DEC31468D patent/DE386054C/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE928724C (en) * | 1948-12-07 | 1955-06-10 | Ciba Geigy | Process for the preparation of insoluble azo dyes |
| FR2232576A1 (en) * | 1973-06-08 | 1975-01-03 | Hoechst Ag | |
| US5266110A (en) * | 1991-11-01 | 1993-11-30 | Hoechst Aktiengesellschaft | Crystal modification of C.I. Pigment Yellow 16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE386054C (en) | Process for the preparation of water-insoluble azo dyes | |
| DE1795051A1 (en) | New water-insoluble monoazo dyes and processes for their preparation | |
| DE393722C (en) | Process for the preparation of water-insoluble azo dyes | |
| DE393267C (en) | Process for the preparation of water-insoluble azo dyes | |
| DE2144907C3 (en) | New water-insoluble mono- and disazo compounds, processes for their preparation and their use as pigments | |
| DE918634C (en) | Process for the production of dye-fast dyeings on acetyl cellulose and linear polyamides or polyurethanes | |
| DE574463C (en) | Process for the preparation of water-insoluble monoazo dyes | |
| DE1544534B2 (en) | Use of 3,3'-dichlorodiphenyl disazo pigment mixtures for the production of graphic printing inks and colors of plastic materials | |
| DE391984C (en) | Process for the preparation of water-insoluble azo dyes | |
| DE692648C (en) | Process for the production of azo dyes | |
| DE395917C (en) | Process for the preparation of water-insoluble azo dyes | |
| DE402868C (en) | Process for the preparation of azo dyes | |
| DE2028395A1 (en) | ||
| DE600823C (en) | Process for the production of water-insoluble azo dyes | |
| DE390666C (en) | Process for the preparation of water-insoluble azo dyes | |
| DE556477C (en) | Process for the preparation of azo dyes | |
| DE118392C (en) | ||
| DE390740C (en) | Process for the preparation of water-insoluble azo dyes | |
| DE1088632B (en) | Process for the preparation of a water-insoluble monoazo dye | |
| DE2601208A1 (en) | Dispersion dye mixts. contg. monoazo dye of benzene series - giving improved light fastness on synthetic fibres | |
| DE433211C (en) | Process for the preparation of water-insoluble azo dyes | |
| DE256999C (en) | ||
| DE888290C (en) | Process for the preparation of monoazo dyes | |
| DE1110786B (en) | Process for the preparation of acetone-soluble conversion products of metallized azo dyes | |
| DE532081C (en) | Process for the preparation of stilbene dyes |