CH435495A - Process for the preparation of hydrazine derivatives - Google Patents

Process for the preparation of hydrazine derivatives

Info

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
Application number
CH470961A
Other languages
German (de)
Inventor
Roland Dr Entschel
Curt Dr Mueller
Walter Dr Wehrli
Original Assignee
Sandoz Ag
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to FR86220D priority Critical patent/FR86220E/fr
Application filed by Sandoz Ag filed Critical Sandoz Ag
Priority to CH470961A priority patent/CH435495A/en
Priority to CH489862A priority patent/CH496765A/en
Priority to CH1807966A priority patent/CH473778A/en
Priority to CH865268A priority patent/CH476072A/en
Priority to GB15063/62A priority patent/GB1004284A/en
Priority to DES79098A priority patent/DE1215842B/en
Priority to NL277500D priority patent/NL277500A/en
Priority to US188837A priority patent/US3252967A/en
Priority to US188889A priority patent/US3252965A/en
Priority to FR895275A priority patent/FR1325176A/en
Priority to DE19621444716 priority patent/DE1444716A1/en
Priority to DE19621444715 priority patent/DE1444715A1/en
Priority to FR895325A priority patent/FR81967E/en
Priority to FR895326A priority patent/FR1331981A/en
Priority to GB1552762A priority patent/GB1009432A/en
Priority to GB15528/62A priority patent/GB1008636A/en
Priority to CH1826468A priority patent/CH521425A/en
Priority to CH823562A priority patent/CH460981A/en
Priority to CH1669466A priority patent/CH473861A/en
Priority to CH1523462A priority patent/CH507350A/en
Priority to CH1523362A priority patent/CH507349A/en
Priority to CH1523262A priority patent/CH507348A/en
Priority to NL287693A priority patent/NL128604C/en
Priority to GB1362/63A priority patent/GB1016515A/en
Priority to NL287692A priority patent/NL128818C/en
Priority to NL287692D priority patent/NL287692A/en
Priority to NL287694D priority patent/NL287694A/en
Priority to NL287693D priority patent/NL287693A/en
Priority to NL287694A priority patent/NL128819C/en
Priority to GB1361/63A priority patent/GB1017611A/en
Priority to FR921239A priority patent/FR83221E/en
Priority to FR921238A priority patent/FR83220E/en
Priority to FR921237A priority patent/FR83219E/en
Priority to FR937104A priority patent/FR83746E/en
Priority to DE19631444726 priority patent/DE1444726A1/en
Priority to BE634601D priority patent/BE634601A/en
Priority to NL295721D priority patent/NL295721A/en
Priority to DE19631444735 priority patent/DE1444735A1/en
Priority to BE641357A priority patent/BE641357A/fr
Priority to FR957741A priority patent/FR84990E/en
Priority to GB50670/63A priority patent/GB1072235A/en
Priority to NL6402587A priority patent/NL6402587A/xx
Priority to DE19641644643 priority patent/DE1644643A1/en
Priority to DE19641644642 priority patent/DE1644642A1/en
Priority to DE19641644632 priority patent/DE1644632A1/en
Priority to GB1069264A priority patent/GB1061461A/en
Priority to FR269A priority patent/FR87090E/en
Priority to GB41165A priority patent/GB1095121A/en
Priority to NL6500323A priority patent/NL6500323A/xx
Priority to NL6500322A priority patent/NL6500322A/xx
Priority to NL6500324A priority patent/NL6500324A/xx
Priority to DE19651644321 priority patent/DE1644321C3/en
Priority to DE19651644322 priority patent/DE1644322C3/en
Priority to DE19651644320 priority patent/DE1644320C3/en
Priority to FR2236A priority patent/FR87385E/en
Priority to US545776A priority patent/US3515733A/en
Priority to US546194A priority patent/US3337523A/en
Priority to US546192A priority patent/US3341514A/en
Priority to US585717A priority patent/US3457260A/en
Publication of CH435495A publication Critical patent/CH435495A/en
Priority to US648962A priority patent/US3560476A/en
Priority to US884042A priority patent/US3583998A/en

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)

PATENTANSPRÜCHE I. Verfahren zur Herstellung von Hydrazinderivaten der Formel EMI0006.0005 worin A den Rest eines Farbstoffs, y ein zweiwertiges Radikal, R1 und R., gleiche oder verschiedene, gegebenenfalls substituierte Alkyl-, Aralkyl- oder Cycloalkylreste oder R1, R2 und -N- oder R1, PATENT CLAIMS I. Process for the preparation of hydrazine derivatives of the formula EMI0006.0005 wherein A is the radical of a dye, y is a divalent radical, R1 and R., identical or different, optionally substituted alkyl, aralkyl or cycloalkyl radicals or R1, R2 and -N- or R1, -N- und y zusam men ein heterocyclisches Ringsystem und n eine ganze Zahl bedeuten, dadurch gekennzeichnet, dass man ein Amin der Formel EMI0006.0021 mit mindestens einem Mol eines Halogenamins umsetzt. II. Verwendung der nach dem Verfahren gemäss Patentanspruch I erhaltenen Farbstoffe zum Färben von Kunststoffmassen. UNTERANSPRÜCHE 1. Verfahren nach Patentanspruch I, dadurch ge kennzeichnet, dass das Halogenanion gegen ein anderes Anion ausgetauscht wird. -N- and y together are a heterocyclic ring system and n is an integer, characterized in that an amine of the formula EMI0006.0021 with at least one mole of a haloamine. II. Use of the dyestuffs obtained by the process according to patent claim I for coloring plastic compositions. SUBClaims 1. The method according to claim I, characterized in that the halogen anion is exchanged for another anion. 2. Verfahren nach Patentanspruch I, dadurch ge kennzeichnet, dass A für den Rest eines Monoazofarb- stoffs steht. 3. Verfahren nach Patentanspruch I, dadurch ge kennzeichnet, dass A für den Rest eines Dis- oder Poly- azofarbstoffs steht. 4. Verfahren nach Patentanspruch I, dadurch ge kennzeichnet, dass A für den Rest eines Anthrachinon- farbstoffs steht. 2. The method according to claim I, characterized in that A stands for the remainder of a monoazo dye. 3. The method according to claim I, characterized in that A represents the remainder of a dis- or poly azo dye. 4. The method according to claim I, characterized in that A represents the remainder of an anthraquinone dye.
CH470961A 1961-04-21 1961-04-21 Process for the preparation of hydrazine derivatives CH435495A (en)

Priority Applications (62)

Application Number Priority Date Filing Date Title
FR86220D FR86220E (en) 1961-04-21
CH470961A CH435495A (en) 1961-04-21 1961-04-21 Process for the preparation of hydrazine derivatives
CH489862A CH496765A (en) 1961-04-21 1961-04-21 Basic anthraquinone dyes for polymers of - acrylonitrile and copolymers of acrylonitrile and vinyl ace
CH1807966A CH473778A (en) 1961-04-21 1962-01-12 Process for the preparation of hydrazine derivatives
CH865268A CH476072A (en) 1961-04-21 1962-01-12 Process for the production of azo dyes
GB15063/62A GB1004284A (en) 1961-04-21 1962-04-18 Basic dyes containing hydrazinium groups
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
US188837A US3252967A (en) 1961-04-21 1962-04-19 Azo basic dyes
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
DE19621444716 DE1444716A1 (en) 1961-04-21 1962-04-21 Process for the production of basic dyes
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
FR895326A FR1331981A (en) 1961-04-21 1962-04-21 Water-soluble reactive dyes, their manufacturing processes and applications
GB1552762A GB1009432A (en) 1961-04-21 1962-04-24 Water-soluble reactive dyes containing hydrazinium groups
GB15528/62A GB1008636A (en) 1961-04-21 1962-04-24 Basic dyes containing hydrazinium groups
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
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
CH1523462A CH507350A (en) 1961-04-21 1962-12-28 (azo) dyestuffs prodn
CH1523362A CH507349A (en) 1961-04-21 1962-12-28 (azo) dyestuffs prodn
CH1523262A CH507348A (en) 1961-04-21 1962-12-28 (azo) dyestuffs prodn
NL287693A NL128604C (en) 1961-04-21 1963-01-11 PROCESS FOR THE PREPARATION OF AZO COLORING AGENTS
GB1362/63A GB1016515A (en) 1961-04-21 1963-01-11 Basic monoazo dyes and their production
NL287692A NL128818C (en) 1961-04-21 1963-01-11 PROCESS FOR THE PREPARATION OF AZO COLORING AGENTS
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
NL287693D NL287693A (en) 1961-04-21 1963-01-11 PROCESS FOR THE PREPARATION OF COLORING AGENTS
NL287694A NL128819C (en) 1961-04-21 1963-01-11 PROCESS FOR THE PREPARATION OF AZO COLORING AGENTS
GB1361/63A GB1017611A (en) 1961-04-21 1963-01-11 Basic monoazo dyes and their production
FR921239A FR83221E (en) 1961-04-21 1963-01-12 Basic dyes, their manufacturing processes and their applications
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
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
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
DE19641644632 DE1644632A1 (en) 1961-04-21 1964-03-13 Process for the production of basic anthraquinone dyes
GB1069264A GB1061461A (en) 1961-04-21 1964-03-13 Basic anthraquinone dyes containing hydrazinium groups, their production and use
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
NL6500322A NL6500322A (en) 1961-04-21 1965-01-12
NL6500324A NL6500324A (en) 1961-04-21 1965-01-12
DE19651644321 DE1644321C3 (en) 1961-04-21 1965-01-14 Basic monoazo dyes and process for their preparation
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
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

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Publication Number Publication Date
CH435495A true CH435495A (en) 1967-05-15

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Country Link
CH (1) CH435495A (en)

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