CH435495A - Process for the preparation of hydrazine derivatives - Google Patents
Process for the preparation of hydrazine derivativesInfo
- Publication number
- CH435495A CH435495A CH470961A CH470961A CH435495A CH 435495 A CH435495 A CH 435495A CH 470961 A CH470961 A CH 470961A CH 470961 A CH470961 A CH 470961A CH 435495 A CH435495 A CH 435495A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- formula
- remainder
- preparation
- hydrazine derivatives
- Prior art date
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
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/001—Dyes containing an onium group attached to the dye skeleton via a bridge
- C09B69/002—Hydrazinium 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/62—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an ethylenimino or N—acylated ethylenimino group or a —CO—NH—CH2—CH2—X group, wherein X is a halogen atom, a quaternary ammonium group or O—acyl and acyl is derived from an organic or inorganic acid, or a beta—substituted ethylamine group
- C09B62/66—Azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung von Hydrazinderivaten Gegenstand der Erfindung ist ein Verfahren zur Her stellung von Hydrazinderivaten der Formel
EMI0001.0006
worin A den Rest eines Farbstoffs, y ein zweiwertiges Radikal, R1 und R2 gleiche oder verschiedene, gegebenenfalls substituierte Alkyl-, Aralkyl- oder Cycloalkylreste oder R1, R2 und N- oder R1,
-N- und y zusammen ein heterocyclisches Ringsystem und n eine ganze Zahl bedeuten, welches dadurch gekennzeichnet ist, dass man ein Amin der Formel
EMI0001.0018
mit n Mol eines Halogenamins, vorzugsweise Chloramin oder Bromamin, umsetzt.
Als Farbstoffe kommen beispielsweise solche der Nitroso-, Nitro-, Styryl-, Stilben-, Di- und Triaryl- methan-, Methin- und Polymethin-, Schwefel-, Anthra- chinon-, Chinonimin-, Azin-, Oxazin-, Thiazin-, Perinon-, Naphthochinon-, Indigo-, Chinophthalon-,
Pyrazolon-, Xanthen-, Acridin-, Chinolin-, Cyanin- Azo- methin-, Phthalocyanin- oder Reaktivfarbstoffreie und insbesondere der Reihe der Mono-, Dis- oder Polyazo- farbstoffe in Betracht, die koordinativ gebundene Me- tallatome enthalten können. Sie gehören z.
B. der Benzol- azo-benzol-, Benzol-azo-naphthalin-, Benzol-azo-pyr- azolon-, Benzol-azo-acyl-essigsäure-arylamid-, Benzol- azo-phenol-, Benzo#l-azo-benzol-azo-phenol-, Thiazol- azo-benzol-, Thia-diazol-azopyrazolon-, Pyridin-azo- indol- oder Chinolin-azo-benzolreihe an.
Als Substituen- ten in diesen kommen vorzugsweise solche in Frage, die in Acetatseiden- und Polyesterfarbstoffen üblich sind, z. B.
Halogenatome oder Cyan-, Nitro- oder Hydroxyl- gruppen oder gegebenenfalls substituierte Alkyl-, Alk- oxy-, Alkylsulfonyl-, Alkoxycarbonyl-, Alkylcarbonyl- oxy-, Carbonsäureamid- oder Sulfonsäureamidgruppen.
Als Brückenglied y eignen sich vorzugsweise gegebe nenfalls substituierte Alkylengrappen, die von Hetero- atomen unterbrochen sein können. y kann auch z. B. mit R1 und N- ein Ringsystem bilden, so dass Ringgrup- pierungen wie z. B.
EMI0001.0096
entstehen.
Die Umsetzung des Amins der Formel (II) mit dem Halogenamin erfolgt vorzugsweise in. einem organischen Lösungsmittel und bei Temperaturen von -50 bis +80 C.
Man kann die Umsetzung aber auch in wäss- rigem Medium, gegebenenfalls unter Zugabe eines orga nischen Lösungsmittels, bei den zuvorgenannten Tem peraturen durchführen, wobei das Halogenamin entwe der gasförmig oder in einem organischen Lösungsmittel oder in Wasser oder in Mischungen von Lösungsmitteln angewendet werden kann.
Die erhaltenen Hydrazinderivate können z. B. durch Abfiltrieren, gegebenenfalls nach Einengen oder Ausfäl len, erhalten werden. Im Verlauf der Abtrennung oder in einer weiteren Stufe lassen sich die Halogenanionen gegen andere Anionen austauschen, z.
B. gegen Methyl- sulfat, Äthylsulfat-, Sulfat-, Disulfat-, Perchlorat-, Chlorid-, Bromid-, Iodid-, Phosphat-, Phosphor- molybdat-, Benzolsulfonat-, Acetat-, Propionat oder Benzoationen oder auch gegen komplexe Anionen, z. B. das von Chlorzinkdoppelsalzen.
Die neuen Farbstoffe dienen vorzugsweise zum Fär ben, Klotzen oder Bedrucken von Formkörpern, insbe sondere Fasern, Fäden oder daraus hergestellten Tex tilien, aus Polymerisaten aus mehr als 80 % Acrylnitril,
beispielsweise aus Polyacrylnitril oder Copolymeren aus 80 bis 95 % Acrylnitril und 20-5 % Vinylacetat, Meth- ylacrylat oder Methylmethacrylat usw.
Man färbt be sonders vorteilhaft in wässrigem, neutralem oder saurem Medium bei Siedetemperatur oder bei Temperaturen über 100 C unter Druck. Hierbei werden auch ohne Anwendung von Retardern sehr egale Färbungen erhal ten. Auch Mischgewebe, welche einen Polyacrylnitril- faseranteil enthalten, lassen sich sehr gut färben.
Dieje nigen Farbstoffe, welche eine gute Löslichkeit in orga nischen Lösungsmitteln besitzen, sind auch zum Färben von natürlichen plastischen Massen oder gelösten oder ungelösten Kunststoff-, Kunstharz- oder Naturharzmas- sen geeignet. So kann Polyacrylnitril in der Masse in licht und nassechten Tönen gefärbt werden. Einzelne der neuen Farbstoffe können zum Beispiel zum Färben von tannierter Baumwolle, Wolle, Seide, regenerierter Cellulose, synthetischen Polyamiden und von Papier eingesetzt werden.
Es hat sich gezeigt, dass man auch vorteilhaft Gemische aus zwei oder mehreren der neuen Farbstoffe verwenden kann. Die erhaltenen Färbungen und Drucke haben eine gute Licht-, Wasch-, Schweiss-, Sublimations-, Plissier-, Dekatur-, Bügel-, Wasser-, Meerwasser-, Trockenreinigungs-, Überfärbe- und Lö- sungsmittelechtheit.
In den folgenden Beispielen bedeuten die Teile Ge wichtsteile und die Prozente Gewichtsprozente. Die Temperaturen sind in Celsiusgraden angegeben.
<I>Beispiel 1</I> In eine mit 375 Teilen Chlorbenzol verdünnte Lö sung von 3,7 Teilen 2-Chlor-4-nitro-4'-(N-äthyl-N-di- methyl-aminoäthyl-amino)-1,1'-azobenzol in 100 Teilen Dimethylformamid leitet man bei 20 während 30 Minu ten einen nach den Angaben von Sisler und Omietanski (Inorganic Synthesis, V, 92)
erzeugten Chloraminstrom ein und rührt anschliessend das Gemisch weitere 6 Stun den. Der ausgefallene Farbstoff der Formel
EMI0002.0071
wird abfiltriert, mit wenig Alkohol gewaschen und getrocknet. Schmelzpunkt: 240 .
<I>Beispiel 2</I> Setzt man 3,4 Teile 1-Methylamino-4-(y-dimethyl- amino-n-propylamino)-anthrachinon, 100 Teile Di- methylformamid und 300 Teile Chlorbenzol ein und verfährt im übrigen nach den Angaben des Beispiels 1, so erhält man einen blauen Farbstoff der Formel
EMI0002.0081
<I>Beispiel 3</I> Den orangen Disazofarbstoff der Formel
EMI0002.0083
kann man aus dem entsprechenden Amin durch Um setzen mit Chloramin gemäss Beispiel 1 erhalten.
Weitere wertvolle Farbstoffe, welche nach den An- gaben in den Beispielen 1 bis 3 hergestellt werden kön nen, werden in der folgenden Tabelle A beschrieben. Sie entsprechen der Formel
EMI0002.0087
Als Anion kommen die in der Beschreibung aufgeführten in Betracht.
EMI0003.0001
EMI0004.0001
EMI0005.0001
EMI0006.0001
Process for the preparation of hydrazine derivatives The invention relates to a process for the preparation of hydrazine derivatives of the formula
EMI0001.0006
wherein A is the radical of a dye, y is a divalent radical, R1 and R2 are identical or different, optionally substituted alkyl, aralkyl or cycloalkyl radicals or R1, R2 and N- or R1,
-N- and y together are a heterocyclic ring system and n is an integer, which is characterized in that an amine of the formula
EMI0001.0018
with n mol of a halogenamine, preferably chloramine or bromamine, reacted.
Examples of dyes are those of the nitroso, nitro, styryl, stilbene, di and triaryl methane, methine and polymethine, sulfur, anthraquinone, quinonimine, azine, oxazine, thiazine -, perinone, naphthoquinone, indigo, quinophthalone,
Pyrazolone, xanthene, acridine, quinoline, cyanine, azomethine, phthalocyanine or reactive dye-free and in particular the series of mono-, dis- or polyazo dyes which may contain coordinatively bonded metal atoms. You belong e.g.
B. benzene azo-benzene, benzene-azo-naphthalene, benzene-azo-pyr-azolone, benzene-azo-acyl-acetic acid-arylamide, benzene-azo-phenol-, benzo # l-azo- benzene-azo-phenol, thiazole-azo-benzene, thia-diazol-azopyrazolone, pyridine-azo-indole or quinoline-azo-benzene series.
Suitable substituents in these are preferably those which are customary in acetate silk and polyester dyes, e.g. B.
Halogen atoms or cyano, nitro or hydroxyl groups or optionally substituted alkyl, alkoxy, alkylsulfonyl, alkoxycarbonyl, alkylcarbonyl oxy, carboxamide or sulfonic acid amide groups.
Optionally substituted alkylene groups, which can be interrupted by heteroatoms, are preferably suitable as bridge members y. y can also be z. B. form a ring system with R1 and N-, so that ring groupings such. B.
EMI0001.0096
arise.
The reaction of the amine of the formula (II) with the haloamine is preferably carried out in an organic solvent and at temperatures from -50 to +80 C.
However, the reaction can also be carried out in an aqueous medium, optionally with the addition of an organic solvent, at the temperatures mentioned above, the haloamine being able to be used either in gaseous form or in an organic solvent or in water or in mixtures of solvents.
The hydrazine derivatives obtained can, for. B. by filtering off, if necessary after concentration or Ausfäl len, can be obtained. In the course of the separation or in a further stage, the halogen anions can be exchanged for other anions, e.g.
B. against methyl sulfate, ethyl sulfate, sulfate, disulfate, perchlorate, chloride, bromide, iodide, phosphate, phosphorus molybdate, benzenesulfonate, acetate, propionate or benzoate ions or against complex anions , e.g. B. that of zinc chloride double salts.
The new dyes are preferably used for dyeing, padding or printing moldings, in particular special fibers, threads or textiles made from them, made from polymers made from more than 80% acrylonitrile,
for example from polyacrylonitrile or copolymers of 80 to 95% acrylonitrile and 20-5% vinyl acetate, methyl acrylate or methyl methacrylate, etc.
It is particularly advantageous to dye in an aqueous, neutral or acidic medium at the boiling point or at temperatures above 100 ° C. under pressure. In this way, very level dyeings are obtained even without the use of retarders. Mixed fabrics which contain a proportion of polyacrylonitrile fibers can also be dyed very well.
Those dyes which have good solubility in organic solvents are also suitable for coloring natural plastic masses or dissolved or undissolved plastic, synthetic resin or natural resin masses. In this way, polyacrylonitrile can be colored in light and wet-fast tones. Some of the new dyes can, for example, be used to dye tannin cotton, wool, silk, regenerated cellulose, synthetic polyamides and paper.
It has been shown that mixtures of two or more of the new dyes can also advantageously be used. The dyeings and prints obtained have good fastness to light, washing, perspiration, sublimation, pleating, decatur, ironing, water, seawater, dry cleaning, over-dyeing and solvent fastness.
In the following examples, the parts are parts by weight and the percentages are percentages by weight. The temperatures are given in degrees Celsius.
<I> Example 1 </I> In a solution diluted with 375 parts of chlorobenzene and containing 3.7 parts of 2-chloro-4-nitro-4 '- (N-ethyl-N-dimethyl-aminoethyl-amino) - 1,1'-azobenzene in 100 parts of dimethylformamide is passed at 20 for 30 minutes according to the information from Sisler and Omietanski (Inorganic Synthesis, V, 92)
generated chloramine stream and then stirred the mixture for a further 6 hours. The unusual dye of the formula
EMI0002.0071
is filtered off, washed with a little alcohol and dried. Melting point: 240.
<I> Example 2 </I> 3.4 parts of 1-methylamino-4- (γ-dimethylamino-n-propylamino) anthraquinone, 100 parts of dimethylformamide and 300 parts of chlorobenzene are used and the rest of the procedure is followed according to the information in Example 1, a blue dye of the formula is obtained
EMI0002.0081
<I> Example 3 </I> The orange disazo dye of the formula
EMI0002.0083
can be obtained from the corresponding amine by reacting with chloramine according to Example 1.
Other valuable dyes which can be prepared according to the information in Examples 1 to 3 are described in Table A below. They correspond to the formula
EMI0002.0087
The anion listed in the description are suitable.
EMI0003.0001
EMI0004.0001
EMI0005.0001
EMI0006.0001
Claims (1)
Priority Applications (62)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR86220D FR86220E (en) | 1961-04-21 | ||
CH489862A CH496765A (en) | 1961-04-21 | 1961-04-21 | Basic anthraquinone dyes for polymers of - acrylonitrile and copolymers of acrylonitrile and vinyl ace |
CH470961A CH435495A (en) | 1961-04-21 | 1961-04-21 | Process for the preparation of hydrazine derivatives |
CH865268A CH476072A (en) | 1961-04-21 | 1962-01-12 | Process for the production of azo dyes |
CH1807966A CH473778A (en) | 1961-04-21 | 1962-01-12 | Process for the preparation of hydrazine derivatives |
GB15063/62A GB1004284A (en) | 1961-04-21 | 1962-04-18 | Basic dyes containing hydrazinium groups |
US188837A US3252967A (en) | 1961-04-21 | 1962-04-19 | Azo basic dyes |
DES79098A DE1215842B (en) | 1961-04-21 | 1962-04-19 | Process for the production of water-soluble reactive dyes |
NL277500D NL277500A (en) | 1961-04-21 | 1962-04-19 | PROCESS FOR THE PREPARATION OF BASIC COLORING AGENTS |
US188889A US3252965A (en) | 1961-04-21 | 1962-04-19 | Azo basic dyes |
FR895275A FR1325176A (en) | 1961-04-21 | 1962-04-20 | Basic dyes, their manufacturing processes and their preparations |
DE19621444715 DE1444715A1 (en) | 1961-04-21 | 1962-04-21 | Process for the production of basic dyes |
FR895325A FR81967E (en) | 1961-04-21 | 1962-04-21 | BASIC COLORANTS, THEIR MANUFACTURING METHODS AND THEIR APPLICATIONS |
DE19621444716 DE1444716A1 (en) | 1961-04-21 | 1962-04-21 | Process for the production of basic dyes |
FR895326A FR1331981A (en) | 1961-04-21 | 1962-04-21 | Water-soluble reactive dyes, their manufacturing processes and applications |
CH1826468A CH521425A (en) | 1961-04-21 | 1962-04-24 | Basic monoazo dyestuffs are produced by the coupling of diazo compds. of amines (I) with compds. (II) For dyeing and printing of polymers with more than 8 |
GB15528/62A GB1008636A (en) | 1961-04-21 | 1962-04-24 | Basic dyes containing hydrazinium groups |
GB1552762A GB1009432A (en) | 1961-04-21 | 1962-04-24 | Water-soluble reactive dyes containing hydrazinium groups |
CH823562A CH460981A (en) | 1961-04-21 | 1962-07-09 | Process for the preparation of hydrazine derivatives |
CH1669466A CH473861A (en) | 1961-04-21 | 1962-12-21 | Process for the production of azo dyes |
CH1523262A CH507348A (en) | 1961-04-21 | 1962-12-28 | (azo) dyestuffs prodn |
CH1523462A CH507350A (en) | 1961-04-21 | 1962-12-28 | (azo) dyestuffs prodn |
CH1523362A CH507349A (en) | 1961-04-21 | 1962-12-28 | (azo) dyestuffs prodn |
NL287692D NL287692A (en) | 1961-04-21 | 1963-01-11 | PROCESS FOR THE PREPARATION OF COLORING AGENTS |
NL287694D NL287694A (en) | 1961-04-21 | 1963-01-11 | PROCESS FOR THE PREPARATION OF COLORING AGENTS |
GB1361/63A GB1017611A (en) | 1961-04-21 | 1963-01-11 | Basic monoazo dyes and their production |
NL287693A NL128604C (en) | 1961-04-21 | 1963-01-11 | PROCESS FOR THE PREPARATION OF AZO COLORING AGENTS |
NL287694A NL128819C (en) | 1961-04-21 | 1963-01-11 | PROCESS FOR THE PREPARATION OF AZO COLORING AGENTS |
NL287692A NL128818C (en) | 1961-04-21 | 1963-01-11 | PROCESS FOR THE PREPARATION OF AZO COLORING AGENTS |
NL287693D NL287693A (en) | 1961-04-21 | 1963-01-11 | PROCESS FOR THE PREPARATION OF COLORING AGENTS |
GB1362/63A GB1016515A (en) | 1961-04-21 | 1963-01-11 | Basic monoazo dyes and their production |
FR921238A FR83220E (en) | 1961-04-21 | 1963-01-12 | Basic dyes, their manufacturing processes and their applications |
FR921237A FR83219E (en) | 1961-04-21 | 1963-01-12 | Basic dyes, their manufacturing processes and their applications |
FR921239A FR83221E (en) | 1961-04-21 | 1963-01-12 | Basic dyes, their manufacturing processes and their applications |
FR937104A FR83746E (en) | 1961-04-21 | 1963-06-05 | Water-soluble reactive dyes, their manufacturing processes and applications |
DE19631444726 DE1444726A1 (en) | 1961-04-21 | 1963-07-05 | Process for the production of basic dyes |
BE634601D BE634601A (en) | 1961-04-21 | 1963-07-05 | BASIC COLORANTS, THEIR MANUFACTURING METHODS AND THEIR APPLICATIONS |
NL295721D NL295721A (en) | 1961-04-21 | 1963-07-24 | PROCESS FOR THE PREPARATION OF BASIC COLORING AGENTS |
DE19631444735 DE1444735A1 (en) | 1961-04-21 | 1963-12-16 | Process for the production of dyes |
BE641357A BE641357A (en) | 1961-04-21 | 1963-12-16 | |
FR957741A FR84990E (en) | 1961-04-21 | 1963-12-19 | Basic dyes, their manufacturing processes and their applications |
GB50670/63A GB1072235A (en) | 1961-04-21 | 1963-12-23 | Dyes containing n-acyl-hydrazinium groups, their production and use |
NL6402587A NL6402587A (en) | 1961-04-21 | 1964-03-12 | |
GB1069264A GB1061461A (en) | 1961-04-21 | 1964-03-13 | Basic anthraquinone dyes containing hydrazinium groups, their production and use |
DE19641644632 DE1644632A1 (en) | 1961-04-21 | 1964-03-13 | Process for the production of basic anthraquinone dyes |
DE19641644643 DE1644643A1 (en) | 1961-04-21 | 1964-03-13 | Process for the production of basic dyes |
DE19641644642 DE1644642A1 (en) | 1961-04-21 | 1964-03-13 | Process for the production of basic anthraquinone dyes |
FR269A FR87090E (en) | 1961-04-21 | 1964-12-29 | Basic dyes, their manufacturing processes and their applications |
GB41165A GB1095121A (en) | 1961-04-21 | 1965-01-05 | Process for the production of mono-azo basic dyes |
NL6500323A NL6500323A (en) | 1961-04-21 | 1965-01-12 | |
NL6500324A NL6500324A (en) | 1961-04-21 | 1965-01-12 | |
NL6500322A NL6500322A (en) | 1961-04-21 | 1965-01-12 | |
DE19651644322 DE1644322C3 (en) | 1961-04-21 | 1965-01-14 | Basic monoazo dyes, process for their preparation and their use |
DE19651644320 DE1644320C3 (en) | 1961-04-21 | 1965-01-14 | Basic monoazo dyes and process for their preparation |
DE19651644321 DE1644321C3 (en) | 1961-04-21 | 1965-01-14 | Basic monoazo dyes and process for their preparation |
FR2236A FR87385E (en) | 1961-04-21 | 1965-01-16 | Basic dyes, their manufacturing processes and their applications |
US545776A US3515733A (en) | 1961-04-21 | 1966-04-27 | Basic dyes |
US546194A US3337523A (en) | 1961-04-21 | 1966-04-29 | Basic monoazo and disazo dyestuffs containing a hydrazinium group |
US546192A US3341514A (en) | 1961-04-21 | 1966-04-29 | Basic monoazo and disazo dyestuffs containing a hydrazinium group |
US585717A US3457260A (en) | 1961-04-21 | 1966-10-06 | Basic methine dyestuffs containing a hydrazinium group |
US648962A US3560476A (en) | 1961-04-21 | 1967-06-26 | Basic monoazo and disazo dyes containing hydroxyethyl hydrazinium groups |
US884042A US3583998A (en) | 1961-04-21 | 1969-12-10 | Basic dyes |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH470961A CH435495A (en) | 1961-04-21 | 1961-04-21 | Process for the preparation of hydrazine derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
CH435495A true CH435495A (en) | 1967-05-15 |
Family
ID=4281134
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH470961A CH435495A (en) | 1961-04-21 | 1961-04-21 | Process for the preparation of hydrazine derivatives |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH435495A (en) |
-
1961
- 1961-04-21 CH CH470961A patent/CH435495A/en unknown
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