CH510624A - Basic derivs. of nitro-para-phenylene diamine - used in hair colouring compsns. - Google Patents

Basic derivs. of nitro-para-phenylene diamine - used in hair colouring compsns.

Info

Publication number
CH510624A
CH510624A CH924768A CH924768A CH510624A CH 510624 A CH510624 A CH 510624A CH 924768 A CH924768 A CH 924768A CH 924768 A CH924768 A CH 924768A CH 510624 A CH510624 A CH 510624A
Authority
CH
Switzerland
Prior art keywords
radical
nitro
formula
compound
lower alkyl
Prior art date
Application number
CH924768A
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
Application filed by Oreal filed Critical Oreal
Publication of CH510624A publication Critical patent/CH510624A/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
    • C09B51/00—Nitro or nitroso 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Abstract

Hair-colouring compositions contain in aqs. soln. at least one nitroparaphenylenediamine dye of formula: (in which R, R' and R" are H, lower alkyl or lower hydroxyalkyl, and R''' is where the amino group may be quaternized, and R1 and R2 are H, lower alkyl or lower hydroxyalkyl, or form a heterocyclic ring with the adjacent N-atom, and n is 2-6 when the NO2 group is ortho to the NR'R" radical, one of R' and R" can be H; when the NO2 group is ortho to the NR'R''' radical and R is H, R1 and R2 are not both ethyl and R' and R" are not both H; when the NO2 group is ortho to the NR'R" radical and R is H, R1 and R2 cannot both be ethyl and R" is not methyl when R' is H. When NO2 is meta to NRR''' only of R' may be H.) The compositions contains 0.1-3.8% dye and have a pH of 6-10. They are applied at room temp. for 5-30 minutes, the hair being subsequently rinsed, shampooed and dried. The dyes show great resistance to light and washing, and they can be used in combination with thickeners, detergents, solvents and lacquers.

Description

       

  
 



  Procédé de préparation de nitroparaphénylènediamines N-arylsulfonylées N'-substituées
 Il est bien connu d'utiliser la nitroparaphénylènediamine et ses produits de substitution comme colorants pour cheveux et autres fibres kératiniques.



   La présente invention concerne un procédé de préparation de nouvelles N-arylsulfonyl, N-o-alkylène-amino,
N'-acétyl-amino, nitroparaphénylènediamines qui représentent un produit intermédiaire pour la préparation de nitroparaphénylènediamines, et en particulier de celles utilisées pour la teinture des fibres kératiniques et spécialement des cheveux.



   La présente invention a pour objet un procédé de préparation de composés de formule:
EMI1.1     
 dans laquelle:
   Rj    et   R2,    identiques ou différents, représentent un atome d'hydrogène, un radical alkyle inférieur ou un radical hydroxyalkyle inférieur, Ri et R2 pouvant également former avec l'atome d'azote sur lequel ils sont fixés un hétérocycle,
 n est un nombre entier compris entre 2 et 6 inclus,
   R0    désigne un atome d'hydrogène, un radical alkyle inférieur ou hydroxyalkyle inférieur,
 Ri désigne un atome d'hydrogène ou un radical méthyle, procédé caractérisé par le fait que   l'on    fait réagir un composé de formule:
EMI1.2     
 éventuellement sous forme de halogénohydrate et en présence d'un hydroxyde alcalin, formule dans laquelle:

  :
 X est un halogène,
 n,   Rt    et R2 ont les significations précitées, sur un composé de formule:
EMI1.3     
 dans laquelle:
   R3    et R4 ont les significations précitées, et
 Me désigne un métal alcalin ou alcalino-terreux.



   On peut ensuite extraire l'halogénohydrate obtenu d'abord par un solvant puis par un hydracide halogéné, par exemple l'acide chlorhydrique, normal et glacé et précipiter le composé de formule (I) attendu par alcali   nidation    de l'halogénohydrate.



   On peut préparer ce composé de formule (III), ser  vant de matière de départ, de la façon indiquée dans le brevet suisse   No    457491, par action du benzène sulfo   chlomre    ou du para-toluène sulfochlorure sur un ami   no-l,    nitro-2, alkyl- ou   hydroxyaWyl-acétamino-4    benzène en solution dans la pyridine, puis en traitant le sul fonamide mono-substitué ainsi obtenu soit par un hydrooxyde alcalin ou alcalino-terreux, soit par un alcoolate alcalin ou un amidure alcalin.



     Exemple    I   s      phase:    Préparation du   N-benzènesulfonylamino-1,   
 nitro-2, (N'-méthyl, N'-acétyl)-amino-4, ben
 zène.



   Ce produit est préparé de façon connue, par action du benzènesulfochlorure sur l'amino-1, nitro-2, méthylacétamino-4, benzène en solution dans la pyridine.



   Après recristallisation dans l'alcool, ce produit fond à   144    C. Son analyse donne les résultats suivants:    Analyse:   
 Calculé pour
   C,,H,,N,O,S    Trouvé
   C 0/o    51,57 51,38-51,30
   Ho/o    4,29 4,32- 4,43
   N /o    12,03 12,23-12,18   3C phase:    Préparation du (N-benzène-sulfonyl,   N- < 3-di-   
 éthyl aminoéthyl)-amino-l, nitro-2, (N'-mé
 thyl, N'-acétyl)amino-4, benzène.



   A une solution de 0,05 mole de N-benzènesulfonylamino-l, nitro-2, (N'-méthyl, N'-acétyl)amino-4, benzène (c'est-à-dire 17,4g) dans 60cm3 de soude normale, on ajoute peu à peu, vers 600 C et simultanément, d'une part, 0,152 mole de chlorhydrate de diéthylamino-éthylchlorure (c'est-à-dire 26 g) en solution dans   100 cm3    d'eau et, d'autre part, 100 cm3 de soude deux fois normale. L'addition terminée, on maintient le mélange réactionnel 3 heures à 600 C. Après refroidissement, on extrait à l'acétate d'éthyle, on lave cette solution d'acétate d'éthyle à la soude normale puis à l'eau pour éliminer le produit initial sous forme de tosylate. On extrait ensuite le produit par l'acide chlorhydrique normal glacé sous forme de chlorhydrate.

  Par alcalinisation de cette solution chlorhydrique à l'aide de soude normale, on précipite 9 g de (N-benzènesulfonyl   N-,8-diéthylamino-    éthyl)-amino-1, nitro-2, (N'-méthyl,   N'-acétyl)amino-4    benzène qui, après recristallisation dans le mélange toluène-hexane, fond à   1280 C.    Son analyse donne les résultats suivants:
 Analyse:
 Calculé pour
   C21H28O5N4S    Trouvé
   C 0/o    56,25 56,43-56,23
   H /o    6,25 6,29- 6,15
   NO/o    12,50 12,67-12,68
 Exemple 2   1-    phase: Préparation du   N-p-toluène-sulfonylamino- 1,   
 nitro-2, acétylamino-4, benzène.



   Ce produit est préparé de la manière habituelle, par action du p-toluène sulfochlorure sur l'amino-1, nitro-2, acétylamino-4, benzène en solution dans la pyridine.



   Après recristallisation dans l'alcool, ce produit fond à 161,50 C et son analyse donne les résultats suivants:
 Analyse:
 Calculé pour
   C15H15N0O5S    Trouvé
 C   O/o    51,57 51,51-51,77
   H O/o    4,29 4,42- 4,12
   NO/o    12.03 12,11-12,12 2e phase: Préparation du N-p-toluènesulfonyl,   N-B-di-   
 éthylaminoéthyl, amino-1, nitro-2, acétylami
 no-4 benzène.



   A une solution de 0,0286 mole de N-p-toluène-sulfo   nylamino- 1,    nitro-2, acétylamino-4, benzène (c'est-à-dire 10 g) dans 40 cm3 de soude normale, on ajoute peu à peu, vers 600 C et simultanément, d'une part   0,086 mole    de chlorhydrate de   p-diéthylamino-éthylchlorure    (c' est-àdire 14,8 g) en solution dans   50 cl2    et d'autre part, 60   cm    de soude deux fois normale. L'addition terminée, on maintient le mélange réactionnel 3 heures à 600 C.

 

  Après refroidissement, on extrait à l'acétate d'éthyle, on lave cette solution d'acétate d'éthyle à la soude, puis à l'eau pour éliminer le produit initial sous forme de tosylate. On extrait ensuite par l'acide chlorhydrique normal glacé le produit sous forme de chlorhydrate. Par alcalinisation de cette solution chlorhydrique à l'aide de soude normale, on précipite 7 g de (N-p-toluènesulfonyl,   N-ss-diéthylaminoéthyl)-amino-1,    nitro-2, acétylamino-4, benzène qui, séché sous vide puis recristallisé dans le mélange toluène-hexane, fond à 1660 C.



   L'analyse de ce produit donne les résultats suivants:
 Analyse:
 Calculé pour
   C21H28O0N4S    Trouvé
   C 0/o    56,25 56,13-56,30
   H /o    6,25 6,29- 6,32
   N  /o    12,50 12,40-12,45 



  
 



  Process for the preparation of N-arylsulfonylated N'-substituted nitroparaphenylenediamines
 It is well known to use nitroparaphenylenediamine and its substitutes as dyes for hair and other keratin fibers.



   The present invention relates to a process for the preparation of novel N-arylsulfonyl, N-o-alkylene-amino,
N'-acetylamino, nitroparaphenylenediamines which represent an intermediate product for the preparation of nitroparaphenylenediamines, and in particular those used for dyeing keratin fibers and especially the hair.



   The present invention relates to a process for the preparation of compounds of formula:
EMI1.1
 in which:
   Rj and R2, which are identical or different, represent a hydrogen atom, a lower alkyl radical or a lower hydroxyalkyl radical, Rj and R2 also being able to form, with the nitrogen atom to which they are attached, a heterocycle,
 n is an integer between 2 and 6 inclusive,
   R0 denotes a hydrogen atom, a lower alkyl or lower hydroxyalkyl radical,
 Ri denotes a hydrogen atom or a methyl radical, a process characterized in that a compound of formula is reacted:
EMI1.2
 optionally in the form of a hydrohalide and in the presence of an alkali metal hydroxide, formula in which:

  :
 X is halogen,
 n, Rt and R2 have the abovementioned meanings, on a compound of formula:
EMI1.3
 in which:
   R3 and R4 have the above meanings, and
 Me denotes an alkali or alkaline earth metal.



   The halohydrate obtained can then be extracted firstly with a solvent and then with a halogenated hydracid, for example hydrochloric acid, normal and ice-cold, and the expected compound of formula (I) can be precipitated by alkali nidation of the halohydrate.



   This compound of formula (III) can be prepared, as a starting material, as shown in Swiss Patent No. 457491, by the action of benzene sulfochloride or para-toluene sulfochloride on a friend no-1, nitro- 2, alkyl- or hydroxyWyl-acetamino-4 benzene in solution in pyridine, then by treating the mono-substituted sulphonamide thus obtained either with an alkaline or alkaline-earth hydrooxide, or with an alkali alcoholate or an alkali amide.



     Example I s phase: Preparation of N-benzenesulfonylamino-1,
 2-nitro, (N'-methyl, N'-acetyl) -amino-4, ben
 zene.



   This product is prepared in a known manner, by the action of benzenesulfochloride on amino-1, nitro-2, methylacetamino-4, benzene in solution in pyridine.



   After recrystallization from alcohol, this product melts at 144 C. Its analysis gives the following results: Analysis:
 Calculated for
   C ,, H ,, N, O, S Found
   C 0 / o 51.57 51.38-51.30
   Ho / o 4.29 4.32- 4.43
   N / o 12.03 12.23-12.18 3C phase: Preparation of (N-benzene-sulfonyl, N- <3-di-
 ethyl aminoethyl) -amino-1, nitro-2, (N'-me
 thyl, N'-acetyl) amino-4, benzene.



   Has a solution of 0.05 mol of N-benzenesulfonylamino-l, nitro-2, (N'-methyl, N'-acetyl) amino-4, benzene (i.e. 17.4g) in 60cm3 of normal soda, is added little by little, at around 600 C and simultaneously, on the one hand, 0.152 mole of diethylamino-ethylchloride hydrochloride (that is to say 26 g) in solution in 100 cm3 of water and, d on the other hand, 100 cm3 of twice normal soda. When the addition is complete, the reaction mixture is maintained for 3 hours at 600 ° C. After cooling, it is extracted with ethyl acetate, this ethyl acetate solution is washed with normal sodium hydroxide and then with water to remove the initial product in the form of tosylate. The product is then extracted with ice cold normal hydrochloric acid in the form of hydrochloride.

  By alkalinization of this hydrochloric solution using normal sodium hydroxide, 9 g of (N-benzenesulfonyl N-, 8-diethylamino-ethyl) -amino-1, nitro-2, (N'-methyl, N'- acetyl) 4-amino benzene which, after recrystallization from a toluene-hexane mixture, melts at 1280 C. Its analysis gives the following results:
 Analysis:
 Calculated for
   C21H28O5N4S Found
   C 0 / o 56.25 56.43-56.23
   H / o 6.25 6.29-6.15
   NO / o 12.50 12.67-12.68
 Example 2 1- phase: Preparation of N-p-toluene-sulfonylamino-1,
 2-nitro, 4-acetylamino, benzene.



   This product is prepared in the usual manner, by the action of p-toluene sulfochloride on amino-1, nitro-2, acetylamino-4, benzene in solution in pyridine.



   After recrystallization from alcohol, this product melts at 161.50 C and its analysis gives the following results:
 Analysis:
 Calculated for
   C15H15N0O5S Found
 C O / o 51.57 51.51-51.77
   H O / o 4.29 4.42- 4.12
   NO / o 12.03 12.11-12.12 2nd phase: Preparation of N-p-toluenesulfonyl, N-B-di-
 ethylaminoethyl, amino-1, nitro-2, acetylami
 no-4 benzene.



   To a solution of 0.0286 mol of Np-toluene-sulfonylamino-1, nitro-2, acetylamino-4, benzene (that is to say 10 g) in 40 cm3 of normal sodium hydroxide, is added little by little , around 600 C and simultaneously, on the one hand 0.086 mole of p-diethylamino-ethylchloride hydrochloride (i.e. 14.8 g) in solution in 50 cl2 and on the other hand, 60 cm of twice normal sodium hydroxide . When the addition is complete, the reaction mixture is maintained for 3 hours at 600 ° C.

 

  After cooling, extraction is carried out with ethyl acetate, this ethyl acetate solution is washed with sodium hydroxide and then with water to remove the initial product in the form of tosylate. The product is then extracted with ice-cold normal hydrochloric acid in the form of hydrochloride. By alkalinization of this hydrochloric solution using normal sodium hydroxide, 7 g of (Np-toluenesulfonyl, N-ss-diethylaminoethyl) -amino-1, nitro-2, acetylamino-4, benzene are precipitated which, dried under vacuum then recrystallized from toluene-hexane, melts at 1660 C.



   Analysis of this product gives the following results:
 Analysis:
 Calculated for
   C21H28O0N4S Found
   C 0 / o 56.25 56.13-56.30
   H / o 6.25 6.29-6.32
   N / o 12.50 12.40-12.45

Claims (1)

REVENDICATION Procédé de préparation de composés de formule: EMI2.1 dans laquelle: Rl et R2, identiques ou différents, représentent un atome d'hydrogène, un radical alkyle inférieur ou un radical hydroxyalkyle inférieur, R1 et R2 pouvant égale ment former avec l'atome d'azote sur lequel ils sont fixés un hétérocycle, n est un nombre entier compris entre 2 et 6 inclus, Rw désigne un atome d'hydrogène, un radical alkyle inférieur ou hydroxyalkyle inférieur, R3 désigne un atome d'hydrogène ou un radical méthyle, procédé caractérisé par le fait que l'on fait réagir un composé de formule EMI3.1 dans laquelle: X est un halogène, n, R1 et RI ont les significations précitées, sur un composé de formule: CLAIM Process for the preparation of compounds of formula: EMI2.1 in which: R1 and R2, identical or different, represent a hydrogen atom, a lower alkyl radical or a lower hydroxyalkyl radical, R1 and R2 also being able to form, with the nitrogen atom to which they are attached, a heterocycle, n is an integer between 2 and 6 inclusive, Rw denotes a hydrogen atom, a lower alkyl or lower hydroxyalkyl radical, R3 denotes a hydrogen atom or a methyl radical, a process characterized in that a compound of formula is reacted. EMI3.1 in which: X is halogen, n, R1 and RI have the abovementioned meanings, on a compound of formula: : EMI3.2 dans laquelle: Rs et R4 ont les significations précitées, et Me désigne un métal alcalin ou alcalino-terreux. : EMI3.2 in which: Rs and R4 have the above meanings, and Me denotes an alkali or alkaline earth metal. SOUS-REVENDICATIONS 1. Procédé selon la revendication, caractérisé par le fait que l'on effectue la réaction dans un solvant aprotonique et de préférence dans le diméthylformamide. SUB-CLAIMS 1. Method according to claim, characterized in that the reaction is carried out in an aprotonic solvent and preferably in dimethylformamide. 2. Procédé selon la revendication, caractérisé par le fait que l'on fait réagir le composé: EMI3.3 sous forme d'halogénohydrate en présence d'un hydrooxyde alcalin. 2. Method according to claim, characterized in that the compound is reacted: EMI3.3 in the form of a halohydrate in the presence of an alkaline hydrooxide. 3. Procédé selon la sous-revendication 2, caractérisé par le fait que l'on extrait 1'halogénohydrate obtenu d'abord par un solvant puis par un hydracide halogéné, par exemple l'acide chlorhydrique normal, et glacé. 3. Method according to sub-claim 2, characterized in that one extracts the halohydrate obtained first with a solvent and then with a halogenated hydracid, for example normal hydrochloric acid, and ice cold. 4. Procédé selon la sous-revendication 2, caractérisé par le fait que l'on obtient le composé (I) par alcalinisation de son halogénohydrate. 4. Method according to sub-claim 2, characterized in that the compound (I) is obtained by alkalinization of its halohydrate.
CH924768A 1965-07-30 1966-07-28 Basic derivs. of nitro-para-phenylene diamine - used in hair colouring compsns. CH510624A (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
LU49213 1965-07-30
LU49214 1965-07-30
LU50348 1966-01-27
LU51474A LU51474A1 (en) 1965-07-30 1966-07-04
CH1096866A CH518096A (en) 1965-07-30 1966-07-28 Dyeing composition for keratin fibers

Publications (1)

Publication Number Publication Date
CH510624A true CH510624A (en) 1971-07-31

Family

ID=27483554

Family Applications (8)

Application Number Title Priority Date Filing Date
CH1082066A CH457491A (en) 1965-07-30 1966-07-26 Process for preparing di-substituted N- (w-haloalkyl) -sulfonamides
CH1617971A CH524370A (en) 1965-07-30 1966-07-28 Dyeing composition for keratin fibers
CH1096866A CH518096A (en) 1965-07-30 1966-07-28 Dyeing composition for keratin fibers
CH924468A CH518902A (en) 1965-07-30 1966-07-28 Process for the preparation of basic derivatives of nitroparaphenylenediamine
CH924568A CH519465A (en) 1965-07-30 1966-07-28 Process for the preparation of new basic derivatives of nitroparaphenylenediamine
CH924768A CH510624A (en) 1965-07-30 1966-07-28 Basic derivs. of nitro-para-phenylene diamine - used in hair colouring compsns.
CH924868A CH519466A (en) 1965-07-30 1966-07-28 Process for the preparation of nitroparaphenylenediamine derivatives
CH924668A CH516507A (en) 1965-07-30 1966-07-28 Process for the preparation of novel hydroxyalkylated derivatives of nitroparaphenylenediamine

Family Applications Before (5)

Application Number Title Priority Date Filing Date
CH1082066A CH457491A (en) 1965-07-30 1966-07-26 Process for preparing di-substituted N- (w-haloalkyl) -sulfonamides
CH1617971A CH524370A (en) 1965-07-30 1966-07-28 Dyeing composition for keratin fibers
CH1096866A CH518096A (en) 1965-07-30 1966-07-28 Dyeing composition for keratin fibers
CH924468A CH518902A (en) 1965-07-30 1966-07-28 Process for the preparation of basic derivatives of nitroparaphenylenediamine
CH924568A CH519465A (en) 1965-07-30 1966-07-28 Process for the preparation of new basic derivatives of nitroparaphenylenediamine

Family Applications After (2)

Application Number Title Priority Date Filing Date
CH924868A CH519466A (en) 1965-07-30 1966-07-28 Process for the preparation of nitroparaphenylenediamine derivatives
CH924668A CH516507A (en) 1965-07-30 1966-07-28 Process for the preparation of novel hydroxyalkylated derivatives of nitroparaphenylenediamine

Country Status (10)

Country Link
US (1) US3665036A (en)
AT (4) AT279053B (en)
BE (2) BE684859A (en)
CH (8) CH457491A (en)
DE (3) DE1617699B2 (en)
FR (2) FR1506350A (en)
GB (2) GB1164824A (en)
IT (1) IT1048380B (en)
LU (4) LU49213A1 (en)
NL (4) NL6610757A (en)

Families Citing this family (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3867456A (en) * 1965-07-30 1975-02-18 Oreal Mono-omega-haloalkyl amines
US3925474A (en) * 1968-05-16 1975-12-09 Oreal Nitroparaphenylene diamine derivatives and methods of making them
LU60732A1 (en) * 1970-04-15 1972-03-02
US4058562A (en) * 1975-09-10 1977-11-15 Pfizer Inc. Antiviral substituted (phenylenedimethylene) diamines
FR2361447A1 (en) * 1976-08-12 1978-03-10 Oreal COLORING COMPOUNDS CONSISTING OF WATER-SOLUBLE CATIONIC POLYMERS AND TINCTORIAL COMPOSITIONS CONTAINING THEM
PT73492B (en) * 1980-08-08 1982-10-28 Oreal TINCTORIAL HAIR COMPOSITIONS BASED ON DIRECT NITROGEN COLORANTS AND DYEING METHOD USING THE SAME
LU83686A1 (en) * 1981-10-08 1983-06-08 Oreal TINCTORIAL COMPOSITION FOR KERATINIC FIBERS BASED ON BENZENIC NITER DYES
FR2519251B1 (en) * 1982-01-05 1985-11-22 Oreal TINCTORIAL COMPOSITION BASED ON PRECURSORS OF OXIDATION DYES AND N-SUBSTITUTED ORTHONITRANILINES COMPRISING AN ALCANOLAMINE AND SODIUM BISULFITE AND THEIR USE IN DYEING KERATIN FIBERS
FR2571364B1 (en) * 1984-10-09 1987-07-17 Oreal NEW PROCESS FOR THE PREPARATION OF N, NON-DISUBSTITUTED NITROPARAPHENYLENEDIAMINES N, NEW OXAZOLIDONES USED IN THIS PROCESS, NEW NITROPARAPHENYLENEDIAMINES N, N'-DISUBSTITUEES OBTAINED BY THIS PROCESS AND COMPOSITIONS TINCTUTINE
US4727192A (en) * 1984-12-13 1988-02-23 L'oreal 2,4-dinitro- or 2-amino-4-nitro- or 2-nitro-4-amino-6-hydroxyalkylanilines, the process for preparation thereof and their use in dyeing keratinous fibers, and especially human hair
LU85681A1 (en) * 1984-12-13 1986-07-17 Oreal NOVELS NITRO-2, AMINO-4, HYDROXYALKYL-6 ANILINES, PROCESS FOR THEIR PREPARATION AND THEIR USE IN DYEING KERATINIC FIBERS AND IN PARTICULAR HUMAN HAIR
LU85939A1 (en) * 1985-06-10 1987-01-13 Oreal NOVEL NITRATED METAPHENYLENEDIAMINES, HALOGENATED IN POSITION 6 AND THEIR USE IN DYEING KERATIOUS MATERIALS
LU86309A1 (en) * 1986-02-14 1987-09-10 Oreal COMPOSITION FOR KERATINIC FIBERS AND IN PARTICULAR FOR HUMAN HAIR, BASED ON HALOGENATED NITROANILINS, DYEING METHOD USING THE SAME DYE COMPOSITION AND NEW HALOGENATED 2-NITROANILINES
LU86308A1 (en) * 1986-02-14 1987-09-10 Oreal TINCTORIAL COMPOSITION FOR KERATINIC FIBERS BASED ON 2-NITROMETAPHENYLENEDIAMINES, PROCESS FOR PREPARING THESE COMPOUNDS AND NOVEL 2-NITRO-METAPHENYLENEDIAMINES USED
FR2724560B1 (en) 1994-09-21 1996-12-20 Oreal PROCESS FOR DIRECT DYING OF KERATINIC FIBERS USING CATIONIC DIRECT DYES AND WATER VAPOR
FR2788220B1 (en) 1999-01-08 2001-02-16 Oreal USE OF CATIONIC DI-BENZENIC NITERS IN DYING KERATINIC FIBERS, TINCTORIAL COMPOSITIONS AND DYING METHODS
FR2788221B1 (en) 1999-01-08 2003-05-30 Oreal USE OF CATIONIC MONOBENZENIC NITROANILINS FOR DYEING KERATINIC FIBERS, DYE COMPOSITIONS AND DYEING METHODS
FR2788273B1 (en) * 1999-01-08 2001-02-16 Oreal CATIONIC MONOBENZENIC NITROPHENYLENEDIAMINES, THEIR USE FOR DYEING KERATINIC FIBERS, TINCTORIAL COMPOSITIONS CONTAINING THEM AND DYEING METHODS
AU2010339735B2 (en) * 2009-12-21 2016-04-14 Living Proof, Inc. Coloring agents and methods of use thereof
FR2968954B1 (en) 2010-12-15 2012-12-21 Oreal PROCESS FOR COLORING KERATIN FIBERS USING A DIRECT DYE WITH PROTECTED DISULFIDE / THIOL / THIOL FUNCTION AND WATER VAPOR
FR2971936B1 (en) 2011-02-25 2013-02-15 Oreal COMPOSITION FOR COLORING KERATIN FIBERS COMPRISING DIRECT DYE WITH DISULFIDE / THIOL FUNCTION, NON-IONIC SURFACTANT, AMPHOTERIC SURFACTANT, ETHOXYL FATTY ALCOHOL, ALKALINE AGENT, AND REDUCING AGENT
FR2971938B1 (en) 2011-02-25 2013-08-02 Oreal COMPOSITION FOR COLORING KERATINIC FIBERS COMPRISING DIRECT COLOR WITH DISULFURE / THIOL FUNCTION, LOW OR NON-ETHOXYL FATTY ALCOHOL, CATIONIC SURFACTANT, ALKALINE AGENT, AND REDUCING AGENT
FR2971937B1 (en) 2011-02-25 2013-02-15 Oreal COMPOSITION FOR COLORING KERATIN FIBERS COMPRISING A DIRECT DYE WITH DISULFURE / THIOL FUNCTION, A NON-CELLULOSIC THICKENING POLYMER, AN ALKALI AGENT, AND A REDUCING AGENT
FR2971935B1 (en) 2011-02-25 2013-02-15 Oreal COMPOSITION FOR COLORING KERATIN FIBERS COMPRISING DIRECT COLOR WITH DISULFIDE / THIOL FUNCTION, THICKENING POLYMER, NON-IONIC SURFACTANT, ALKALINE AGENT, AND REDUCING AGENT
FR2977482B1 (en) 2011-07-05 2013-11-08 Oreal COLORING COMPOSITION USING A LONG CHAIN ETHER OF ALCOXYL FATTY ALCOHOL AND CATIONIC POLYMER, METHODS AND DEVICES
WO2013004772A2 (en) 2011-07-05 2013-01-10 L'oreal Dye composition comprising an alkoxylated fatty alcohol ether and a fatty alcohol
ES2750570T3 (en) 2011-07-05 2020-03-26 Oreal Cosmetic composition rich in fatty substances comprising a polyoxyalkylenated fatty alcohol ether and a direct dye and / or an oxidation dye, staining method and device
BR112015002202B1 (en) 2012-08-02 2019-10-22 Oreal keratin fiber dyeing composition, keratin fiber dyeing process and device
FR2994091B1 (en) 2012-08-02 2014-08-01 Oreal COLORING COMPOSITION COMPRISING NON-IONIC GUAR GUM OR ONE OF ITS NON-IONIC DERIVATIVES, PROCESS AND DEVICE
EP2879650B1 (en) 2012-08-02 2017-07-26 L'oreal Dyeing composition comprising a fatty substance, a non-ionic guar gum, an amphoteric surfactant and a non-ionic or anionic surfactant, and an oxidizing agent, dyeing process and suitable device
FR2994084B1 (en) 2012-08-02 2014-10-31 Oreal CREAM-STAINING COMPOSITION COMPRISING AT LEAST ONE OIL, NO LITTLE OR LESS SOLID FATTY ALCOHOL, COLORING PROCESS AND APPROPRIATE DEVICE
FR3015231B1 (en) 2013-12-23 2017-02-24 Oreal PACKAGING ARTICLE COMPRISING AN ENVELOPE ANHYDROUS COLORING COMPOSITION COMPRISING A DIRECT COLOR, USE AND METHOD FOR COLORING KERATINIC FIBERS
FR3015232B1 (en) 2013-12-23 2016-01-08 Oreal PACKAGING ARTICLE COMPRISING AN ENVELOPE ANHYDROUS COLORING COMPOSITION COMPRISING AN OXIDATION COLOR, USE AND METHOD FOR COLORING KERATIN FIBERS
FR3016288B1 (en) 2013-12-23 2016-09-09 Oreal PACKAGING ARTICLE COMPRISING AN ENVELOPE AND ANHYDROUS COMPOSITION COMPRISING AN OXIDIZING AGENT

Also Published As

Publication number Publication date
CH519465A (en) 1972-02-29
CH524370A (en) 1972-06-30
IT1048380B (en) 1980-11-20
AT277414B (en) 1969-12-29
LU49214A1 (en) 1967-01-30
NL6610757A (en) 1967-01-31
CH516507A (en) 1971-12-15
DE1617699A1 (en) 1971-07-29
AT279053B (en) 1970-02-25
CH519466A (en) 1972-02-29
CH518096A (en) 1972-01-31
DE1569816A1 (en) 1969-11-06
LU49213A1 (en) 1967-01-30
GB1164825A (en) 1969-09-24
FR1506350A (en) 1967-12-22
DE1543810B2 (en) 1978-04-20
DE1617698A1 (en) 1971-04-22
BE684859A (en) 1967-01-30
JPS582204B1 (en) 1983-01-14
FR1491617A (en) 1967-08-11
AT281222B (en) 1970-05-25
CH518902A (en) 1972-02-15
BE684863A (en) 1967-01-30
DE1617699B2 (en) 1975-10-30
CH457491A (en) 1968-06-15
US3665036A (en) 1972-05-23
DE1617698B2 (en) 1975-09-11
LU50348A1 (en) 1967-07-27
DE1543810A1 (en) 1970-02-26
NL6610759A (en) 1967-01-31
AT278988B (en) 1970-02-25
NL7006131A (en) 1970-08-25
NL130871C (en)
LU51474A1 (en) 1968-03-12
DE1543810C3 (en) 1978-12-07
GB1164824A (en) 1969-09-24

Similar Documents

Publication Publication Date Title
CH510624A (en) Basic derivs. of nitro-para-phenylene diamine - used in hair colouring compsns.
US4311478A (en) Paraphenylenediamines substituted at position 2 of the benzene ring
US5334225A (en) Keratinous fiber dye composition containing a 2-substituted amino-5-alkylphenol derivative coupler
RU2197948C2 (en) Application of cationic phenylazobenzene compounds for staining keratin fibers, staining composites and methods of staining
US2750326A (en) Process and composition for dyeing hair
JPS6234752B2 (en)
EP0465342A1 (en) Reducing cosmetic composition for perming containing a derivative of a N-(mercapto-alkyl)succinamic acid or a N-(mercapto-alkyl)succinimid and its use in a process for permanent hair shaping
EP0653202A1 (en) Cosmetic composition containing an N-mercaptoalkyl alkanediamide or one of its cosmetically acceptable salts as a reducing agent
CH622699A5 (en)
CH651542A5 (en) NITER DERIVATIVES OF THE BENZENIC SERIES AND THEIR USE IN DYEING KERATINIC FIBERS.
CH457484A (en) Process for preparing new nitro dyes
FR2606405A1 (en) PROCESS FOR THE PREPARATION OF 5,6-DIHYDROXYINDOLE AND ITS ALKYL DERIVATIVE, THEIR USE IN CAPILLARY DYE AND INTERMEDIATE COMPOUNDS
JPS6155156A (en) Novel diamino-tetrafluoroethoxybenzene and hair dye
EP0359618B1 (en) 2-substituted para-aminophenols and their use in the coloration of keratinic fibres
US4754069A (en) 2-alkyl sulfonyl-1,4-diaminobenzenes, processes for their production and oxidation hair dyeing compositions containing the same
GB2216124A (en) N4-substituted 1-methoxy-2 4-diaminobenzenes
KR890008090A (en) Peroxycarboxylic amino derivative
DE19534214C1 (en) New 4-(2,5-di:amino-phenoxymethyl)-1,3-dioxolane derivs.
CA1175069A (en) Tinctorial composition for keratinic fibres and containing nitro-3-orthophenylenediamines; novel nitro-3-orthophenylenediamines used and processes for their preparation
IL61560A (en) 1-methyl-(or 1-ethyl)-2-(n-allyl-n-(2,6-dichlorophenyl)-amino)-2-imidazolines,their preparation and pharmaceutical compositions containing them
DK0731787T3 (en) Crystalline, polymorphic form of (S, S, S) -N- (1- [2-carboxy-3- (N2-mesyllysylamino) propyl] -1-cyclopentylcarbonyl) tyrosine
US3388148A (en) Nu-cyanoethyl derivatives of nitro-p-phenylenediamine
CA1338689C (en) Sulfur-containing nitroaminobenzene dyes, process and hair dye compositions
ATE20468T1 (en) PROCESS FOR THE PREPARATION OF 4-HYDROXY-3(HETEROCYCLOCARBAMOYL)-2H-1,2-BENZOTHIAZINE-1,1DIOXIDES.
DE69411783T2 (en) Process for the preparation of sulfonylurea derivatives

Legal Events

Date Code Title Description
PL Patent ceased