CH496651A - Process for the preparation of nitro-p-phenylenediamine derivatives - Google Patents

Process for the preparation of nitro-p-phenylenediamine derivatives

Info

Publication number
CH496651A
CH496651A CH264367A CH264367A CH496651A CH 496651 A CH496651 A CH 496651A CH 264367 A CH264367 A CH 264367A CH 264367 A CH264367 A CH 264367A CH 496651 A CH496651 A CH 496651A
Authority
CH
Switzerland
Prior art keywords
nitro
preparation
benzene
phenylenediamine derivatives
hydroxyalkyl
Prior art date
Application number
CH264367A
Other languages
French (fr)
Inventor
Kalopissis Gregoire
Bugaut Andree
Original Assignee
Oreal
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 claimed from LU48467A external-priority patent/LU48467A1/xx
Application filed by Oreal filed Critical Oreal
Publication of CH496651A publication Critical patent/CH496651A/en

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/418—Amines containing nitro groups

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  
 



  Procédé de préparation de dérivés de la nitro-p-phénylène-diamine
 La présente invention a pour objet un procédé de préparation de nouveaux dérivés di-substitués de la nitro-paraphénylènediamine, c'est-à-dire des   amino- 1,    nitro-2,   (o'-hydroxyalcoyl)-aIcoylamino-4,    benzènes correspondant à la formule générale
EMI1.1     
 dans laquelle R désigne un radical alcoyle inférieur, pos   scdant    par exemple de 1 à 4 atomes de carbone, et R' désigne un radical   o-hydroxyalcoyle    inférieur, contenant par exemple de 1 à 4 atomes de carbone.



   Le procédé selon l'invention est caractérisé en ce que   l'on    soumet   l'acétamino-l,      (co'-hydroxyalcoyl)-alcoyl-    amino-4, benzène à une nitration, par exemple avec un mélange sulfonitrique, et que   l'on    effectue sur le produit obtenu une désacétylation, par exemple au moyen d'acide chlorhydrique.



   Les dérivés de formule (I) sont utilisables comme colorants pour fibres kératiniques, en particulier pour la teinture des cheveux vivants.



   Les composés de formule (I) peuvent également être utilisés comme produits de base de synthèse organique permettant d'aboutir à des dérivés tri-substitués de la nitro-paraphénylènediamine.



      Exemple:   
 Préparation de l'amino-l, nitro-2,(2'-hydroxyéthyl)
 méthylamino-4,benzène
 a) Première phase: nitration
 Dans 75 cm3 d'acide sulfurique concentré on dissout 0,1 mole (c'est-à-dire 21 g) d'acétamino-l, (2'-hydroxy
 éthyl)-méthylamino-4, benzène en maintenant la tempé
 rature entre 0 et 20 C. On ajoute aussitôt, peu à peu et sous agitation, en maintenant toujours la température
 entre 0 et 20 C, un mélange sulfonitrique formé par l'addition de 6,6 g d'acide sulfurique concentré à 6,6 g d'acide nitrique ayant pour densité 1,52. On verse le mélange réactionnel sur de la glace, on neutralise à l'ammoniaque et on réalise une extraction à l'alcool isopropylique.



  Après avoir chassé cet alcool sous vide, on obtient 23,5 g d'acétamino-l, nitro-2, (2'-hydroxyéthyl)-amino-4, benzène brut.



  b)   Deuxième    phase: désacétylation et purification
 Le   dérivc    acétylé obtenu dans la première phase est introduit dans un mélange de 30   cm8    d'acide chlorhydrique concentré et de 60cm3 d'eau. On porte alors au bain-marie bouillant pendant 1/2 heure; on ajoute un peu de noir animal, on filtre et on essore après refroidissement 16 g de chlorhydrate cristallisé. On dissout ce chlorhydrate dans l'eau bouillante et on rend le milieu alcalin avec de l'ammoniaque, on refroidit et on essore 13 g   d'amino -l,nitro -    2(2'-hydroxyéthyl)-méthylamino-4, benzène, qui après recristallisation dans le chloroforme, fond   à 1150 C.     

 

   Analyse Calculé du produit obtenu pour   CoHi3OsNs    Trouvé
 C    /o    51,18 51,16-51,22
   H O/o    6,16 6,12- 6,42
   NO/o    19,90 20,03-20,03 



  
 



  Process for the preparation of nitro-p-phenylenediamine derivatives
 The present invention relates to a process for the preparation of new di-substituted derivatives of nitro-paraphenylenediamine, that is to say amino-1, nitro-2, (o'-hydroxyalkyl) -aIcoylamino-4, benzenes corresponding to the general formula
EMI1.1
 in which R denotes a lower alkyl radical, pos scdant for example from 1 to 4 carbon atoms, and R ′ denotes a lower o-hydroxyalkyl radical, containing for example from 1 to 4 carbon atoms.



   The process according to the invention is characterized in that the acetamin-l, (co'-hydroxyalkyl) -alkyl-amino-4, benzene is subjected to nitration, for example with a sulphonitric mixture, and that the deacetylation is carried out on the product obtained, for example by means of hydrochloric acid.



   The derivatives of formula (I) can be used as dyes for keratin fibers, in particular for dyeing living hair.



   The compounds of formula (I) can also be used as basic organic synthesis products making it possible to lead to tri-substituted derivatives of nitro-paraphenylenediamine.



      Example:
 Preparation of amino-l, nitro-2, (2'-hydroxyethyl)
 4-methylamino, benzene
 a) First phase: nitration
 In 75 cm3 of concentrated sulfuric acid, 0.1 mole (that is to say 21 g) of acetamino-l, (2'-hydroxy
 ethyl) -methylamino-4, benzene while maintaining the temperature
 rature between 0 and 20 C. One adds immediately, little by little and with stirring, always maintaining the temperature
 between 0 and 20 C, a sulphonitric mixture formed by the addition of 6.6 g of concentrated sulfuric acid to 6.6 g of nitric acid having a density of 1.52. Pour the reaction mixture onto ice, neutralize with ammonia and extract with isopropyl alcohol.



  After having removed this alcohol under vacuum, 23.5 g of crude acetamino-1, nitro-2, (2'-hydroxyethyl) -amino-4, benzene are obtained.



  b) Second phase: deacetylation and purification
 The acetylated derivative obtained in the first phase is introduced into a mixture of 30 cm8 of concentrated hydrochloric acid and 60 cm3 of water. It is then brought to a boiling water bath for 1/2 hour; a little animal charcoal is added, filtered and after cooling 16 g of crystallized hydrochloride are filtered off. This hydrochloride is dissolved in boiling water and the medium is made alkaline with ammonia, cooled and 13 g of amino -l, nitro - 2 (2'-hydroxyethyl) -methylamino-4, benzene, which, after recrystallization from chloroform, melts at 1150 C.

 

   Calculated Analysis of the Product Obtained for CoHi3OsNs Found
 C / o 51.18 51.16-51.22
   HO / o 6.16 6.12-6.42
   NO / o 19.90 20.03-20.03

Claims (1)

REVENDICATION Procédé de préparation des amino-l, nitro-2,(e3'-hy- droxyalcoyl)-alcoylamino-4,benzènes, de formule EMI2.1 dans laquelle R désigne un radical alcoyle inférieur et R' désigne un radical w-hydroxyalcoyle inférieur, caractérisé en ce que l'on soumet un acétamido-l,(on'-hydroxy- alcoyl)-alcoylamino-4, benzène à une nitration et que l'on effectue sur le produit obtenu une désacétylation. CLAIM Process for the preparation of amino-l, nitro-2, (e3'-hydroxyalkyl) -alkylamino-4, benzenes, of formula EMI2.1 in which R denotes a lower alkyl radical and R 'denotes a lower w-hydroxyalkyl radical, characterized in that an acetamido-1, (on'-hydroxy-alkyl) -alkyllamino-4, benzene is subjected to nitration and which is carried out on the product obtained deacetylation. SOUS-REVENDICATIONS 1. Procédé selon la revendication, caractcrisé en ce que la nitration est opérée avec un mélange sulfonitrique. SUB-CLAIMS 1. Method according to claim, characterized in that the nitration is carried out with a sulphonitric mixture. 2. Procédé selon la revendication, caractérisé en ce que la désacétylation est obtenue par traitement à l'acide chlorhydrique. 2. Method according to claim, characterized in that the deacetylation is obtained by treatment with hydrochloric acid. 3. Procédé selon la revendication ou l'une des sousrevendications précédentes, caractérisé en ce que les radicaux R et R' contiennent chacun de 1 à 4 atomes de carbone. 3. Method according to claim or one of the preceding subclaims, characterized in that the radicals R and R 'each contain from 1 to 4 carbon atoms.
CH264367A 1965-04-26 1966-04-21 Process for the preparation of nitro-p-phenylenediamine derivatives CH496651A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
LU48467A LU48467A1 (en) 1965-04-26 1965-04-26
CH580166A CH445723A (en) 1965-04-26 1966-04-21 Dye composition for hair dyeing

Publications (1)

Publication Number Publication Date
CH496651A true CH496651A (en) 1970-09-30

Family

ID=25698391

Family Applications (3)

Application Number Title Priority Date Filing Date
CH264367A CH496651A (en) 1965-04-26 1966-04-21 Process for the preparation of nitro-p-phenylenediamine derivatives
CH264467A CH501584A (en) 1965-04-26 1966-04-21 Process for the preparation of nitro-p-phenylenediamine derivatives
CH264567A CH496652A (en) 1965-04-26 1966-04-21 Process for the preparation of nitro-p-phenylenediamine derivatives

Family Applications After (2)

Application Number Title Priority Date Filing Date
CH264467A CH501584A (en) 1965-04-26 1966-04-21 Process for the preparation of nitro-p-phenylenediamine derivatives
CH264567A CH496652A (en) 1965-04-26 1966-04-21 Process for the preparation of nitro-p-phenylenediamine derivatives

Country Status (1)

Country Link
CH (3) CH496651A (en)

Also Published As

Publication number Publication date
CH496652A (en) 1970-09-30
CH501584A (en) 1971-01-15

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