DE2359399B2 - Hair dye - Google Patents
Hair dyeInfo
- Publication number
- DE2359399B2 DE2359399B2 DE19732359399 DE2359399A DE2359399B2 DE 2359399 B2 DE2359399 B2 DE 2359399B2 DE 19732359399 DE19732359399 DE 19732359399 DE 2359399 A DE2359399 A DE 2359399A DE 2359399 B2 DE2359399 B2 DE 2359399B2
- Authority
- DE
- Germany
- Prior art keywords
- same
- brown
- red
- triamino
- yellow
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Links
Classifications
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4953—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom containing pyrimidine ring derivatives, e.g. minoxidil
-
- 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
- A61Q5/10—Preparations for permanently dyeing the hair
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
Description
Rs R,. Rs R ,.
'Ν /'Ν /
I NH1 N-\/ R1 IlI NH 1 N - \ / R 1 II
N NN N
ist, in der Ri — R& Wasserstoff, einen Alkylrest mit 1 —4 Kohlenstoffatomen,is, in which Ri - R & hydrogen, an alkyl radical with 1 - 4 carbon atoms,
den Rest -(CH2Jn-X, in dem n=l -4 und X eine Hydroxylgruppe, ein Halogenatom, eine -NH2-, -NHR'- und -NR'R"-Gruppe sind, wobei R' und R" Alkylreste mit 1-4 Kohlenstoffatomen bedeuten oder mit dem Stickstoffatom zu einem heterocyclischen Ring, der ein weiteres Stickstoffatom oder Sauerstoffatom enthalten kann, geschlossen sind,the radical - (CH 2 J n -X, in which n = 1-4 and X is a hydroxyl group, a halogen atom, an -NH 2 -, -NHR'- and -NR'R "group, where R 'and R "denotes alkyl radicals with 1-4 carbon atoms or are closed with the nitrogen atom to form a heterocyclic ring which can contain a further nitrogen atom or oxygen atom,
einen gegebenenfalls substituierten Arylrest, einen gegebenenfalls substituierten heterocyclischen 5- oder 6gliedrigen Ring mit einem oder zwei Stickstoffatomen oder einem Stickstoffatom und einem Sauerstoffatom darstellen, wobei das Tetraaminopyrimidin auch als anorganisches oder organisches Salz vorliegen kann.an optionally substituted aryl radical, an optionally substituted heterocyclic 5- or 6-membered ring with one or two nitrogen atoms or one nitrogen atom and represent an oxygen atom, the tetraaminopyrimidine also being inorganic or organic Salt may be present.
2. Haarfärbemittel nach Anspruch 1, dadurch gekennzeichnet, daß es zusätzlich übliche Entwicklerkomponenfen sowie gegebenenfalls übliche direktziehende Farbstoffe enthält.2. Hair colorant according to claim 1, characterized in that there are also customary developer components and optionally conventional substantive dyes.
3. Haarfärbemittel nach Anspruch 1 und 2, dadurch gekennzeichnet, daß es an Entwickler-Kuppler-Kombination aus Tetraaminopyrimidin und in der Haarfärbung üblicher Kupplerkomponente 0,2 bis 5 Gewichtsprozent, vorzugsweise 1 bis 3 Gewichtsprozent, enthält.3. Hair dye according to claim 1 and 2, characterized in that it is a developer-coupler combination of tetraaminopyrimidine and the coupler component customary in hair coloring 0.2 to 5 percent by weight, preferably 1 to 3 Weight percent, contains.
4. Haarfärbemittel nach Anspruch 1, dadurch gekennzeichnet, daß Ri und R2, R3 und R4 beziehungsweise R5 und Re mit dem jeweiligen Stickstoffatom zu einem gegebenenfalls substituierten heterocyclischen 5- oder ögliedrigen Ring mit einem oder zwei Stickstoffatomen oder einem Stickstoffatom und einem Sauerstoffatom zusammengeschlossen sind.4. Hair dye according to claim 1, characterized in that Ri and R 2 , R3 and R4 or R5 and Re are joined together with the respective nitrogen atom to form an optionally substituted heterocyclic 5- or 6-membered ring with one or two nitrogen atoms or one nitrogen atom and one oxygen atom .
Für das Färben von Haaren spielen die sogenannten Oxidationsfarben, die durch oxidative Kupplung einer Entwicklerkomponente mit einer Kupplerkomponente entstehen, wegen ihrer intensiven Farben und sehr guten Echtheitseigenschaften eine bevorzugte Rolle. Als Entwicklersubstanzen werden üblicherweise Stickstoffbasen, wie p-Pheny!endiaminderivaie, Diaminopyridine,The so-called oxidation colors, which are produced by oxidative coupling, play a role in the coloring of hair Developer components with a coupler component arise because of their intense colors and very good fastness properties play a preferred role. Nitrogen bases are usually used as developer substances, such as p-pheny! endiamine derivatives, diaminopyridines,
4-Amino-pyrazolon-derivate, heterocyclische Hydrazone eingesetzt. Als sogenannte Kupplerkomponenten werden m-Phenylen-diaminderivate, Phenole, Naphthole, Resorcinderivate und Pyrazolone genannt.4-amino-pyrazolone derivatives, heterocyclic hydrazones used. As so-called coupler components, m-phenylene-diamine derivatives, phenols, naphthols, Resorcinol derivatives and pyrazolones called.
Gute Oxidationshaarfarbstoffkomponenten müssen in erster Linie folgende Voraussetzungen erfüllen:Good oxidation hair dye components must primarily meet the following requirements:
Sie müssen bei der oxidativen Kupplung mit den jeweiligen Entwickler- bzw. Kupplerkomponenten die gewünschten Farbnuancen in ausreichender Intensität ausbilden. Sie müssen ferner ein ausreichendes biü sehr gutes Aufziehvermögen auf menschlichem Haar besitzen, und sie sollen darüber hinaus in toxikologischer und dermatologischer Hinsicht unbedenklich sein.You must with the oxidative coupling with the respective developer or coupler components develop the desired color nuances with sufficient intensity. You must also have a sufficient amount of money have good absorption properties on human hair, and they are also said to be toxicological and toxic be dermatologically harmless.
Die üblicherweise als Entwicklersubstanzen verwendete Verbindungsklasse der substituierten bzw. unsubstituierten p-Phenylendiamine besitzt den Nachteil, daß sie bei einer Reihe von Personen Sensibilisierungen und in deren Gefolge schwere Allergien hervorruft. Die zur Vermeidung dieser dermatologischen Nachteile in neuererer Zeit vorgeschlagenen Entwicklersubstanzen können in ihren anwendungstechnischen Eigenschaften nicht immer voll befriedigen.The substituted or unsubstituted compound class commonly used as developer substances p-Phenylenediamines has the disadvantage that they are sensitizations and in a number of people in the wake of which causes severe allergies. To avoid these dermatological disadvantages in Recently proposed developer substances can in their application properties not always fully satisfying.
Es bestand daher bei der Suche nach brauchbaren Oxidationshaarfarbstoffen die Aufgabe, geeignete Komponenten aufzufinden, die vorgenannte Voraussetzungen in optimaler Weise erfüllen.In the search for useful oxidation hair dyes, the task was therefore to find suitable ones Find components that meet the above requirements in an optimal way.
Es wurde nun gefunden, daß daß Haarfärbemittel auf Basis von Oxidationsfarbstoffen mit einem Gehalt an bestimmten Tetraaminopyrimidinen den gestellten Anforderungen in besonders hohem Maße gerecht werden. Erfindungsgegenstand ist daher ein Haarfärbemittel, bestehend aus einer Entwicklerkomponente, einer üblichen Kupplerkomponente und üblichen Zusätzen, dadurch gekennzeichnet, daß die Entwickleirkomponente oin Tetraaminopyrimidin der allgemeinen FormelIt has now been found that hair dyes based on oxidation dyes with a content of certain tetraaminopyrimidines meet the requirements to a particularly high degree will. The subject of the invention is therefore a hair dye, consisting of a developer component, a customary coupler component and customary additives, characterized in that the developer component oin tetraaminopyrimidine of the general formula
R5 R 5
R„R "
NH1 NH 1
V NNV N N
R2 R4 R 2 R 4
ist, in der Ri — Rt Wasserstoff, einen Alkylrest mit I —4 Kohlenstoffatomen,in which Ri - Rt is hydrogen, an alkyl radical with 1-4 carbon atoms,
den Rest -(CH2Jn-X, in dem η= 1 —4 und X eine Hydroxylgruppe, ein Halogenatom, eine -NH2-, -NHR'- und -NR'R"-Gruppe sind, wobei R' und R" Alkylreste mit 1 —4 Kohlenstoffatomen bedeuten oder mit dem Stickstoffatom zu einem heterocyclischen Ring, der ein weiteres Stickstoffatom oder Sauerstoffatom enthalten kann, geschlossen sind,the radical - (CH 2 J n -X, in which η = 1-4 and X is a hydroxyl group, a halogen atom, an -NH 2 -, -NHR'- and -NR'R "group, where R 'and R "denotes alkyl radicals with 1-4 carbon atoms or are closed with the nitrogen atom to form a heterocyclic ring which can contain a further nitrogen atom or oxygen atom,
einen gegebenenfalls substituierten Arylrest,
einen gegebenenfalls substituierten heterocyclischen 5- oder 6gliedrigen Ring mit einem oder zweiStickstoffatomen
oder einem Stickstoffatom und einem Sauerstoffatom darstellen, wobei das Tetraaminopyrimidin
auch als anorganisches oder organisches Salz vorliegen kann.an optionally substituted aryl radical,
represent an optionally substituted heterocyclic 5- or 6-membered ring with one or two nitrogen atoms or one nitrogen atom and one oxygen atom, it also being possible for the tetraaminopyrimidine to be present as an inorganic or organic salt.
Bei ihrem Einsatz als Entwicklerkomponenten liefern die Tetraaminopyrimdänc mit den im allgemeinen fürWhen used as developer components, the Tetraaminopyrimdänc provide with the in general for
die Oxidationshaarfärbung verwendeten Kupplersubstanzen die unterschiedlichsten sehr intensiven Farbnuancen, wie sie mit diesen Kupplern und den bisher bekannten Entwicklern nicht erzielbar waren und stellen somit eine wesentliche Bereicherung der oxidativen Haarfärbemöglichkeiten dar. Darüber hinaus zeichnen sich die Tetraaminopyrimidine durch sehr gute Echtheitseigenschaften der damit erzielten Färbungen, durch eine gute Löslichkeit im Wasser, eine gute Lagerstabilität und toxikologische, sowie dermatologisehe Unbedenklichkeit aus.the oxidation hair coloring used coupler substances the most varied of very intense color nuances, how they could not be achieved with these couplers and the previously known developers and thus represent an essential enrichment of the oxidative hair coloring possibilities. In addition the tetraaminopyrimidines are characterized by very good fastness properties of the dyeings achieved with them, through good solubility in water, good storage stability and toxicological and dermatological Harmlessness.
Die als Entwicklerkomponenten verwendeten Tetraaminopyrimidine können entweder als solche oder in Form ihrer Salze mit anorganischen oder organischen Säuren, wie z.B. als Chloride, Sulfate, Phosphate, Acetate, Propionate, Lactate, Citrate eingesetzt werden. Die Herstellung der meisten dieser Tetraaminopyrimide ist bereits literaturbekannt und kann der Monographie von D. J. B r ο w η, »The Pyrimidines« in der Reihe Heterocyclic Compounds, lnterscience Publishers (1962) Band I und Il entnommen werden. Nur einige wenige der verwendeten Verbindungen stellen neue Substanzen dar, deren Herstellung gesondert beschrieben ist.The tetraaminopyrimidines used as developer components can be used either as such or in the form of their salts with inorganic or organic acids, such as, for example, as chlorides, sulfates, phosphates, acetates, propionates, lactates, citrates. The preparation of most of these tetraaminopyrimides is already known from the literature and can be found in the monograph by DJ Br ο w η, "The Pyrimidines" in the series Heterocyclic Compounds, Interscience Publishers (1962) Volumes I and II. Only a few of the compounds used represent new substances, the preparation of which is described separately.
Zur Synthese der Verbindungen geht man im allgemeinen von 2,4,6-Triaminopyrimidinen aus, in die die 5-Aminogruppe durch Nitrosierung und anschließende Reduktion eingeführt wird. Man kann aber auch von entsprechend substituierten Triamino-alkylmercaptopyrimidinen ausgehen und die Alkylmercaptogruppe durch Amine substituieren. Die letztere Methode eignet sich besonders zur Einführung von Aminogruppen bzw. von substituierten Aminogruppen in die 2-, 4- oder 6-Stellung des Pyrimidinringes.The synthesis of the compounds is generally based on 2,4,6-triaminopyrimidines, in which the 5-amino group is introduced by nitrosation and subsequent reduction. But you can also start from appropriately substituted triamino-alkyl mercaptopyrimidines and the alkyl mercapto group substitute with amines. The latter method is particularly suitable for introducing amino groups or of substituted amino groups in the 2-, 4- or 6-position of the pyrimidine ring.
Als in den erfindungsgemäßen Haarfärbemittel einzusetzende Entwicklerkomponenten sind z. B.
2,4,5,6-Tetraamino-,
4,5-Diamino-2,6-bismethylamino-,
2,5-Diamino-4,6-bismethylamino-,
4,5-Diamino-6-butylamino-2-dimethylamino-,
2,5-Diamino-4-diäthy!amino-6-methylamino-,
4,5-Diamino-6-diäthylamino-2-dimethylamino-,
4,5-Diamino-2-diäthylamino-6-methylamino-,
4,5-Diamino-2-dimethylamino-6-äthylamino-,
4,5-Diamino-2-dimethylamino-6-isopropylamino-,
4,5-Diamino-2-dimethylamino-6-methylamino-,
4,5-Diamino-6-dimethylamino-2-methylamino-,
4,5-Diamino-2-dimethylamino-6-propylamino-,
2,4,5-Triamino-6-dimethylamino-,
4,5,6-Triamino-2-dimethylamino-,
2,4,5-Triamino-6-methylamino-,
4,5,6-Triamino-2-methylamino-,
4,5-Diamino-2-dimethylamino-6-piperidino-,
4,5-Diamino-6-methylamino-2-piperidino-,
2,4,5-Triamino-6-piperidino-,
2,4,5-Triamino-6-anilino-,
2,4,5-Triamino-6-benzylamino-,
2,4,5-Triamino-6-benzylidenamino-,
4,5,6-Triamino-2-piperidino-,
2,4,6-Trismethylamino-5-amino-,
2,4,5-Triamino-6-di-n-propylamino-,
2,4,5-Triamino-6-morpholino-,
2,5,6-Triamino-4-dimethylamino-,
4,5,6-Triamino-2-morpholino-,
2,4,5-Triamino-6-ji-hydroxyäthylamino-,
4,5,6-Triamino-2-j3-amino-äthylamino-,
2,5,6-Triamino-4-jS-methylamino-äthylamino-,
2,5-Diamino-4,6-bis-)>-diäthyIamino-propylamino-,As to be used in the hair dye according to the invention developer components are, for. B.
2,4,5,6-tetraamino,
4,5-diamino-2,6-bismethylamino,
2,5-diamino-4,6-bismethylamino,
4,5-diamino-6-butylamino-2-dimethylamino-,
2,5-diamino-4-diethy! Amino-6-methylamino-,
4,5-diamino-6-diethylamino-2-dimethylamino,
4,5-diamino-2-diethylamino-6-methylamino,
4,5-diamino-2-dimethylamino-6-ethylamino,
4,5-diamino-2-dimethylamino-6-isopropylamino,
4,5-diamino-2-dimethylamino-6-methylamino,
4,5-diamino-6-dimethylamino-2-methylamino,
4,5-diamino-2-dimethylamino-6-propylamino,
2,4,5-triamino-6-dimethylamino-,
4,5,6-triamino-2-dimethylamino-,
2,4,5-triamino-6-methylamino-,
4,5,6-triamino-2-methylamino-,
4,5-diamino-2-dimethylamino-6-piperidino-,
4,5-diamino-6-methylamino-2-piperidino-,
2,4,5-triamino-6-piperidino-,
2,4,5-triamino-6-anilino-,
2,4,5-triamino-6-benzylamino-,
2,4,5-triamino-6-benzylideneamino-,
4,5,6-triamino-2-piperidino-,
2,4,6-trismethylamino-5-amino-,
2,4,5-triamino-6-di-n-propylamino-,
2,4,5-triamino-6-morpholino-,
2,5,6-triamino-4-dimethylamino-,
4,5,6-triamino-2-morpholino-,
2,4,5-triamino-6-ji-hydroxyäthylamino-,
4,5,6-triamino-2-j3-amino-ethylamino-,
2,5,6-triamino-4-jS-methylamino-ethylamino-,
2,5-diamino-4,6-bis -)> - diethyIamino-propylamino-,
4,5-Diamino-2-methylamino-6-|3-hydroxyäthylamino-, 4,5-diamino-2-methylamino-6- | 3-hydroxyethylamino-,
5-Amino-2,4,6-triäthylamino-,
2,4-Bis-/J-hydroxyäthylamino-6-anilinori
5-amino-pyrimidin5-amino-2,4,6-triethylamino-,
2,4-bis- / I-hydroxyethylamino-6-anilino r i 5-aminopyrimidine
zu nennen.to call.
Als Beispiele für in den erfindungsgemäßen Haarfärbemitteln einzusetzende Kupplerkomponenten sindExamples of coupler components to be used in the hair colorants according to the invention are
«-Naphthol, o-Kresol, m-Kresol,
to 2,6-Dimethylphenol, 2,5-Dimethylphenol,"-Naphthol, o-cresol, m-cresol,
to 2,6-dimethylphenol, 2,5-dimethylphenol,
3,4-Dimethylphenol,3,5-Dimethylphenol,
Brenzcatechin, Pyrogallol,
1,5- bzw. 1,7-Dihydroxy-naphthalin,
5-Amino-2-methylphenol, Hydrochinon,
ι ö 2,4-Diamino-anisol, m-Toluylendiamin,3,4-dimethylphenol, 3,5-dimethylphenol,
Catechol, pyrogallol,
1,5- or 1,7-dihydroxynaphthalene,
5-amino-2-methylphenol, hydroquinone,
ι ö 2,4-diamino-anisole, m-toluenediamine,
4-Aminophenol, Resorcin,
Resorcinmonomethyiäther, m-Phenylendiamin,
1 -Phenyl-S-methyl-pyrazolon-S,
1 -Phenyl-S-aminopyrazolon-S,
2Ii l-Phenyl-3,5-diketo-pyrazo(idin,4-aminophenol, resorcinol,
Resorcinol monomethyl ether, m-phenylenediamine,
1-phenyl-S-methyl-pyrazolone-S,
1-phenyl-S-aminopyrazolon-S,
2Ii l-phenyl-3,5-diketo-pyrazo (idin,
l-Methyl-7-dimethyl-amino-4-hydroxy-chinoIon-2I
1 -Amino-S-acetacetylamino^-nitro-benzol oder
l-Amino-3-cyanacetylamino-4-nitro-benzol
anzuführen.l-methyl-7-dimethyl-amino-4-hydroxy-quinoIon-2 I 1 -amino-S-acetacetylamino ^ -nitro-benzene or
l-amino-3-cyanoacetylamino-4-nitro-benzene
to cite.
2r> In den erfindungsgemäßen Haarfärbemitteln werden die Entwicklerkomponenten im allgemeinen in etwa molaren Mengen, bezogen auf die verwendeten Kupplersubstanzen, eingesetzt. Wenn sich auch der molare Einsatz als zweckmäßig erweist, so ist es jedoch ίο nicht nachteilig, wenn die Entwicklerkomponente in einem gewissen Überschuß oder Unterschuß zum Einsatz gelangt.2 r> In the hair dye of the present invention, the developer components generally in about molar amounts, based on the used coupling substances used. If the molar use also proves to be expedient, it is not, however, disadvantageous if the developer component is used in a certain excess or deficiency.
Es ist ferner nicht erforderlich, daß die Entwicklerkomponente und die Kupplersubstanz einheitliche Γ) Produkte darstellen, vielmehr können sowohl die Entwicklerkomponente Gemische der erfindungsgemäß zu verwendenden Tetraaminopyrimidine als auch die Kupplersubstanz Gemische der vorstehend genannten Kupplerkomponenten darstellen.Furthermore, it is not necessary that the developer component and the coupler substance be uniform Γ) represent products, rather both the Developer component mixtures of the tetraaminopyrimidines to be used according to the invention as well as the Coupler substance represent mixtures of the aforementioned coupler components.
4» Darüber hinaus können die erfindungsgemäßen Haarfärbemittel andere bekannte und übliche Entwicklerkomponenten sowie auch gegebenenfalls übliche direktziehende Farbstoffe im Gemisch enthalten, falls dies zur Erzielung gewisser Farbnuancen erforderlich 4r> ist.4 »In addition, hair dyes of the invention, other known and usual developer components and also optionally conventional direct dyes in admixture, if certain to achieve color shades is required 4 r>.
Die oxidative Kupplung, d. h. die Entwicklung der Färbung, kann grundsätzlich wie bei anderen Oxidationshaarfarbstoffen auch, durch Luftsauerstoff erfolgen. Zweckmäßigerweise werden jedoch chemische ™ Oxidationsmittel eingesetzt. Als solche kommen insbesondere Wasserstoffperoxid oder dessen Anlagerungsprodukte an Harnstoff, Melamin und Natriumborat, sowie Gemische aus derartigen Wasserstoffperoxidanlagerungsverbindungen mit Kaliumperoxiddisulfat in 5) Betracht.The oxidative coupling, i.e. H. The development of the color can basically be the same as with other oxidation hair dyes also, done by atmospheric oxygen. However, chemical ™ oxidizing agents are expediently used. As such come in particular Hydrogen peroxide or its addition products with urea, melamine and sodium borate, and mixtures of such hydrogen peroxide addition compounds with potassium peroxide disulfate in 5) consideration.
Als Entwicklerkomponente besitzen dabei die Tetraaminopyrimidine
den Vorteil, daß sie bereits bei oxidativer Kupplung durch Luftsauerstoff voll befriedigende
Färbeergebnisse liefern und somit eine Haarschädigung durch das sonst für die oxidative Kupplung
eingesetzte Oxidationsmittel vermieden werden kann. Wird jedoch gleichzeitig neben der Färbung ein
Aufhelleffekt am Haar gewünscht, so ist die Mitverwendung von Oxidationsmitteln erforderlich.
μ Die erfindungsgemäßen Haarfärbemittel werden für den Einsatz in entsprechende kosmetische Zubereitungen,
wie Cremes, Emulsionen, Gele oder auch einfache Lösungen eingearbeitet und unmittelbar vor derAs a developer component, the tetraaminopyrimidines have the advantage that they give completely satisfactory coloring results even with oxidative coupling by atmospheric oxygen and thus damage to the hair by the oxidizing agent otherwise used for the oxidative coupling can be avoided. However, if at the same time a lightening effect is desired on the hair in addition to the coloring, the use of oxidizing agents is necessary.
μ The hair dyes according to the invention are incorporated into corresponding cosmetic preparations, such as creams, emulsions, gels or simple solutions, and immediately before the use
Anwendung auf dem Haar mit einem der genannten Oxidationsmittel versetzt. Die Konzentration derartiger färberischer Zubereitungen an Kuppler Entwicklerkombination beträgt 0,2 bis 5 Gewichtsprozent, vorzugsweise 1—3 Gewichtsprozent. Zur Herstellung r> von Cremes, Emulsionen oder Gelen werden die Farbstoffkomponenten mit den für derartige Präparationen üblichen weiteren Bestandteilen gemischt. Als solche zusätzlichen Bestandteile sind z. B. Netz- oder Emulgiermittel vom anionischen oder nichtionischen i<> Typ, wie Alkylbenzolsulfonate, Fettdlkoholsulfate, Alkylsulfonate, Fettsäurealkanolamide, Anlagerungsprodukte von Äthylenoxid an Fettalkohole, Verdickungsmittel, wie Methylcellulose, Stärke, höhere Fettalkohole, Paraffinöl, Fettsäuren, ferner Parfümöle und Haarpfle- r> gemittel, wie Pantothensäure und Cholesterin zu nennen. Die genannten Zusatzstoffe werden dabei in den für diese Zwecke üblichen Mengen eingesetzt, wie z. B. Netz- und Emulgiermittel in Konzentrationen von 0,5 — 30 Gewichtsprozent und Verdickungsmittel in 2u Konzentrationen von 0,1 — 25 Gewichtsprozent, jeweils bezogen auf die gesamte Zubereitung.Use on the hair mixed with one of the oxidizing agents mentioned. The concentration of coupler / developer combination in such dyeing preparations is 0.2 to 5 percent by weight, preferably 1-3 percent by weight. To produce r> of creams, emulsions or gels, the dye components are mixed with the customary for such preparations other ingredients. Such additional ingredients are e.g. B. wetting or emulsifying agents of the anionic or nonionic type, such as alkylbenzene sulfonates, fatty alcohol sulfates, alkyl sulfonates, fatty acid alkanolamides, addition products of ethylene oxide with fatty alcohols, thickeners such as methyl cellulose, starch, higher fatty alcohols, paraffin oil, fatty acids and perfume oils > agents, such as pantothenic acid and cholesterol. The additives mentioned are used in the amounts customary for this purpose, such as. As wetting agents and emulsifiers in concentrations of from 0.5 to 30 percent by weight and thickeners in concentrations 2u 0.1 to 25 weight percent, each based on the total preparation.
Die Anwendung der erfindungsgemäßen Haarfärbemittel kann, unabhängig davon, ob es sich um eine Lösung, eine Emulsion, eine Creme oder ein Gel handelt, 2r> im schwach sauren, neutralen oder insbesondere alkalischen Milieu bei einem pH-Wert von 8 bis 10 erfolgen. Die Anwendungstemperaturen bewegen sich dabei im Bereich von 15 bis 400C. Nach einer Einwirkungsdauer von ca. 30 Minuten wird das jo Haarfärbemittel vom zu färbenden Haar durch Spülen entfernt. Hernach wird das Haar mit einem milden Shampoo nachgewaschen und getrocknet.The hair dyes according to the invention may, regardless of whether it is a solution, an emulsion, a cream or a gel, 2 r> in the slightly acidic, neutral or particularly alkaline medium carried out at a pH of 8 to 10 The application temperatures are in the range from 15 to 40 ° C. After an exposure time of about 30 minutes, the hair colorant is removed from the hair to be colored by rinsing. The hair is then washed with a mild shampoo and dried.
Die mit den erfindungsgemäßen Haarfärbemitteln erzielbaren Farbtöne zeigen unter Einsatz unterschied- η licher Entwickler- und Kupplerkomponenten eine außerordentliche Variationsmöglichkeit, die von hellblond bis dunkelbraun und grün bis violett reicht. Die erzielten Färbungen haben gute Licht-, Wasch- und Reibechtheitseigenschaften und lassen sich leicht mit Reduktionsmitteln wieder abziehen.The advantages attainable with the inventive hair dye shades show using different η Licher primary and secondary intermediates an extraordinary possibility of variation which to dark brown and green ranges from blond to purple. The dyeings obtained have good light, washing and rubbing fastness properties and can easily be peeled off again with reducing agents.
4r)4 r )
illill
Zunächst wird die Herstellung einiger in den erfindungsgemäßen Haarfärbemitteln zu verwendenden Tetraaininopyrimidine beschrieben, die bisher nicht literaturbekannt sind.First, the preparation of some to be used in the hair dyes according to the invention Tetraaininopyrimidines described, which are not previously known from the literature.
Darstellung vondisplay of
2,4,6-Trimethylamino-5-amino-pyrimidin-sulfat,2,4,6-trimethylamino-5-aminopyrimidine sulfate,
C7H14N6 · H2SO4 · 2 H2OC 7 H 14 N 6 • H2SO4 • 2 H 2 O
5,5 g 2,4,6-Trismethylaminopyrimidin (nach W i η k
e I m a η η, J. Prakt. Chem., 115, 292, [1927] hergestellt) r.
wurden in 50 ml Wasser gelöst und mit Natriumacetat auf pH 4 gebracht. Die Lösung wurde auf 8O0C erhitzt
und eine Lösung von 1,4 g NaNO2 in 5 ml H2O
hinzugegeben. Es entstand eine rote Lösung. Bei 6O0C wurde so viel Natriumdithionit hinzugegeben, bis die wi
Lösung gelb war. Die gelbe Lösung wurde mit verd. H2SO4 versetzt und der Niederschlag abgesaugt. Ausb
55%.
Fp215°.5.5 g of 2,4,6-trismethylaminopyrimidine (prepared according to W i η k e I ma η η, J. Prakt. Chem., 115, 292, [1927]) r. were dissolved in 50 ml of water and brought to pH 4 with sodium acetate. The solution was heated to 8O 0 C and a solution of 1.4 g NaNO 2 in 5 ml H 2 O added. A red solution resulted. At 6O 0 C as much sodium was added, was to the wi solution yellow. Dilute H2SO4 was added to the yellow solution and the precipitate was filtered off with suction. Yield 55%.
Mp215 °.
Analyse: hl Analysis: St.
Berechnet: C 26,6%, H 6,4%, N 26,6%;
gefunden: C 26,6%, H 8,3%. N 27.7%.Calculated: C 26.6%, H 6.4%, N 26.6%;
found: C 26.6%, H 8.3%. N 27.7%.
Darstellung von 2,4,5-Triamino-6-di-n-propylaminopyrimidindihydrochlorid, CioHjoNt · 2 HClPreparation of 2,4,5-triamino-6-di-n-propylaminopyrimidine dihydrochloride, CioHjoNt · 2 HCl
2,4,5-Triamino-6-di-n-propylamino-pyrimidinsulfai
wurde stufenweise wie folgt dargestellt:2,4,5-triamino-6-di-n-propylamino-pyrimidinesulfai
was shown in stages as follows:
1. 2,4-Diamino-6-di-n-propylamino-pyrimidin1. 2,4-Diamino-6-di-n-propylamino-pyrimidine
15 g 2,4-Diamino-6-cMorpyriniidin (nach R ο t h, B., Smith, J. M., und Hultquist, E. M., J. Am. Chem. Soc, 72, 1914 [1950] hergestellt) wurden in 130 ml Äthanol mit 50 g Di-n-propylamin versetzt und im Autoklav 3 Stunden bei 200°C gehalten (Anfangsdruck 10 atü N2). Nach dem Abkühlen und Öffnen wurde die Reaktionsmischung in einem Eis-Kochsalzbad gekühlt, um Di-propylaminhydrochlorid auszufällen. Es wurde abfiltriert und die Mutterlauge weitgehend eingeengt (ca. 20 ml Rest), wobei 18g = 82,9% Rohprodukt ausfielen; dieses wurde als solches weiterverarbeitet.15 g 2,4-diamino-6-cMorpyriniidin (according to R ο t h, B., Smith, J. M., and Hultquist, E. M., J. Am. Chem. Soc, 72, 1914 [1950]) were in 130 ml of ethanol are mixed with 50 g of di-n-propylamine and kept in the autoclave for 3 hours at 200 ° C (initial pressure 10 atmospheres N2). After cooling down and Opening the reaction mixture was cooled in an ice-saline bath to make di-propylamine hydrochloride to fail. It was filtered off and the mother liquor was largely concentrated (approx. 20 ml of remainder), where 18g = 82.9% crude product precipitated; this was further processed as such.
2. 2,4-Diamino-5-nitroso-6-di-n-propylaminopyrimidin 2. 2,4-Diamino-5-nitroso-6-di-n-propylaminopyrimidine
18 g 2,4-Diamino-6-di-n-propylamino-pyrimidin
(Rohprodukt) wurden in 25 ml Wasser aufgeschlämmt und mit soviel Eisessig versetzt bis pH 4
erreicht war; danach wurde auf 50° erwärmt, wobei die Substanz gelöst war und langsam mit 5,5 g
Natriumnitrit in 10 ml Wasser versetzt; nach kurzer Zeit fiel ein himbeerroter Niederschlag aus;
abgesaugt und getrocknet unter Vakuum bei Raumtemperatur verblieben 9,4 g = 46%.
Smp:206-208°C
Analyse:18 g of 2,4-diamino-6-di-n-propylamino-pyrimidine (crude product) were slurried in 25 ml of water and glacial acetic acid was added until a pH of 4 was reached; it was then heated to 50 °, the substance being dissolved, and 5.5 g of sodium nitrite in 10 ml of water were slowly added; after a short time a raspberry-red precipitate fell out; suctioned off and dried under vacuum at room temperature, 9.4 g = 46% remained.
M.p .: 206-208 ° C
Analysis:
Berechnet: C 50,40%, H 7,61%, N 35,27%;Calculated: C 50.40%, H 7.61%, N 35.27%;
gefunden: C 49,56%, H 7,62%, N 35,50%.found: C 49.56%, H 7.62%, N 35.50%.
3. 2,4,5-Triamino-6-di-n-propylaminopyrimidindihydrochlorid 3. 2,4,5-triamino-6-di-n-propylaminopyrimidine dihydrochloride
6,5 g 2,4-Diamino-5-nitroso-6-di-n-propylaminopyrimidin wurden in 150 ml Äthanol mit 0,5 g
Katalysator (10% Fd auf Kohle) in einer Schüttelente bei Raumtemperatur hydriert. Nach beendeter
H2-Aufnahme wurde vom Katalysator abfiltriert, mit Salzsäure angesäuert und eingeengt.
Rückstand: 5,6 g = 78,8%, braune Kristalle, Zers. Pkt. 1050C. Das Massenspektrum zeigt die
Molekülmasse 224 (Ber. 224)6.5 g of 2,4-diamino-5-nitroso-6-di-n-propylaminopyrimidine were hydrogenated in 150 ml of ethanol with 0.5 g of catalyst (10% Fd on charcoal) in a shaking duck at room temperature. After the uptake of H2 had ended, the catalyst was filtered off, acidified with hydrochloric acid and concentrated.
Residue: 5.6 g = 78.8%, brown crystals, decomp. Point 105 0 C. The mass spectrum shows the molecular mass 224 (Ber. 224)
Darstellung vondisplay of
2,4,5-Triamino-6-morpholino-pyrimidin-sulfat
C8H14N6O · H2SO4 2,4,5-triamino-6-morpholinopyrimidine sulfate
C 8 H 14 N 6 O • H 2 SO 4
2,4,5-Triamino-6-morpholino-pyrimidin-sulfat wurde stufenweise aus folgenden Verbindungen hergestellt:2,4,5-Triamino-6-morpholino-pyrimidine-sulfate was prepared in stages from the following compounds:
1. Zu 10 g 2,4-Diamino-6-chlorpyrimidin (nach R ο t h , B., S m i t h, J. M. und H u 11 q u i s t, E. M.,). Am. Chem. Soc, 72, 1914 [1950] hergestellt) (0,07 Mol) wurden 30 g Morpholin (30 ml 0,34 Mol) zugegeben und unter Rühren innerhalb einer Stunde auf 1000C erwärmt; bei dieser Temperatur wurde die Mischung 272 Stunden gehalten; danach wurden 10 ml Äthanol zugesetzt und im Kühlschrank stehen gelassen, bis Morpholinhydrochlorid ausgefallen war, das abgetrennt wurde. Das Filtrat wurde eingeengt, um das Rohprodukt als halb öligen halb kristallinen Rückstand zu gewinnen (5,9 = 43,7%); als Rohprodukt weitervcrarbeitel. 1. To 10 g of 2,4-diamino-6-chloropyrimidine (according to R ο th, B., S mith, JM and H u 11 quist, EM,). At the. Chem. Soc, 72, 1914 [1950]) (0.07 mol), 30 g of morpholine (30 ml, 0.34 mol) were added and the mixture was heated to 100 ° C. over the course of one hour; the mixture was held at this temperature for 272 hours; then 10 ml of ethanol were added and the mixture was left to stand in the refrigerator until morpholine hydrochloride had precipitated, which was separated off. The filtrate was concentrated to obtain the crude product as a semi-oily semi-crystalline residue (5.9 = 43.7%); continue to be processed as a raw product.
2. 2,4-Diamino-6-morpholino-5-nitroso-pyrimiclin2. 2,4-Diamino-6-morpholino-5-nitroso-pyrimicline
5,9 g 2,4-Diamino-6-morpholino-pyrimidin (0,03 Mol) (Rohprodukt) wurden in 25 ml Wasser unter
Erwärmen gelöst und mit Essigsäure versetzt bis pH 4 erreicht war; danach wurde die Lösung auf
80°C erwärmt und langsam eine Natriumnitritlösung von 2 g in 5 ml Wasser zugegeben; nach
kurzer Zeit fiel die Nitrosoverbindung als himbeerroter Niederschlag aus; durch Einengen und
Kühlen wurden insgesamt 4,1 g = 6O,3°/o Ausbeute erhalten.
Smp:231-233°C5.9 g of 2,4-diamino-6-morpholino-pyrimidine (0.03 mol) (crude product) were dissolved in 25 ml of water while warming, and acetic acid was added until pH 4 was reached; then the solution was heated to 80 ° C. and a sodium nitrite solution of 2 g in 5 ml of water was slowly added; after a short time the nitroso compound precipitated out as a raspberry-red precipitate; concentration and cooling gave a total of 4.1 g = 6O.3% yield.
M.p .: 231-233 ° C
Analyse:Analysis:
Berechnet: C 42,85%, H 5,39%, N 37,48%;
gefunden: C 41,92%, H 4,97%, N 38,22%.Calculated: C 42.85%, H 5.39%, N 37.48%;
found: C 41.92%, H 4.97%, N 38.22%.
3. 2,4,5-Triamino-6-morpholino-pyrimidin-sulfat3. 2,4,5-triamino-6-morpholinopyrimidine sulfate
2,5 g 2,4-Diamino-6-morpholino-5-nitroso-pyΓimidin wurden in 15 ml Wasser aufgeschlämmt und mit 2 n-HCl (5 ml) versetzt, bis die Substanz gerade gelöst war; das Substanzgemisch wurde dann auf 50° erwärmt und langsam wurde soviel Natriumdithionit (Na2S2O4) zugegeben, bis sich die violette Lösung gelb färbte; danach wurde filtriert, abgekühlt und mit Schwefelsäure (1 :1) auf pH 2 eingestellt.2.5 g of 2,4-diamino-6-morpholino-5-nitroso-pyΓimidine were suspended in 15 ml of water and treated with 2N HCl (5 ml) until the substance was just dissolved; the mixture of substances was then heated to 50 ° and sodium dithionite (Na 2 S 2 O 4 ) was slowly added until the purple solution turned yellow; it was then filtered, cooled and adjusted to pH 2 with sulfuric acid (1: 1).
Nach kurzer Zeit fiel das Pyrimidin als Sulfat aus; es wurden 2,6 g = 76,4% erhalten.
Analyse (umkristallisiert):After a short time the pyrimidine precipitated as sulfate; 2.6 g = 76.4% were obtained.
Analysis (recrystallized):
Berechnet: C 31,17%, H 53%, N 27,25%;
gefunden: C 29,81%, H 4,98%, N 27,86%,Calculated: C 31.17%, H 53%, N 27.25%;
found: C 29.81%, H 4.98%, N 27.86%,
Smp: sintert bei 230°; langsame Zersetz, an 255°C Tabelle 1M.p .: sinters at 230 °; slow decomposition, at 255 ° C Table 1
K)K)
1515th
2020th
2525th
30 Die anderen in den nachfolgenden Beispieler eingesetzten Tetraaminopyrimidine sind literaturbekannt, und ihre Herstellung erfolgt auf Wegen, wie sie ir der Monographie von D. J. Brown »The Pyrimidines« in Heterocyclic Compounds, Interscience Publishers 1962 Band I und Il aufgezeigt sind. 30 The other tetraaminopyrimidines used in the following examples are known from the literature, and their preparation takes place in ways as shown in the monograph by DJ Brown "The Pyrimidines" in Heterocyclic Compounds, Interscience Publishers 1962 Vol. I and II.
Die erfindungsgemäßen Haarfärbemittel wurden ir Form einer Cremeemulsion eingesetzt. Dabei wurden ir eine Emulsion ausThe hair colorants according to the invention were used in the form of a cream emulsion. In doing so, ir an emulsion
10 Gew.-Teilen Fettalkoholen der Kettenlänge10 parts by weight of chain length fatty alcohols
Ci2 — C|8Ci2 - C | 8
10 Gew.-Teilen Fettalkoholsulfat (Natriumsalz)10 parts by weight of fatty alcohol sulfate (sodium salt)
Kettenlänge Ci2-CiB
75 Gew.-Teilen WasserChain length Ci 2 -CiB
75 parts by weight of water
jeweils 0,01 MoI der in der nachstehenden Tabelle aufgeführten Tetraaminopyrimidine und Kupplersubstanzen eingearbeitet. Danach wurde der pH-Wert dei Emulsion mittels Ammoniak auf 9,5 eingestellt und die Emulsion mit Wasser auf 100 Gewichtsteile aufgefüllt Die oxidative Kupplung wurde entweder mit Luftsauerstoff oder mit l°/oiger Wasserstoffperoxidlösung als Oxidationsmittel durchgeführt, wobei zu 100 Gewichtsteilen der Emulsion 10 Gewichtsteile Wasserstoffperoxidlösung gegeben wurden. Die jeweilige Färbecreme mit oder ohne zusätzlichem Oxidationsmittel wurde auf zu 90% ergrautes, nicht besonders vorbehandeltes Menschenhaar aufgetragen und dort 30 Minuten belassen. Nach Beendigung des Färbeprozesses wurde das Haar mit einem üblichen Haarwaschmittel ausgewaschen und anschließend getrocknet Die dabei erhaltenen Färbungen sind nachstehender Tabelle 1 zu entnehmen.0.01 mol each of the tetraaminopyrimidines and coupler substances listed in the table below incorporated. The pH of the emulsion was then adjusted to 9.5 using ammonia and the Emulsion made up to 100 parts by weight with water. The oxidative coupling was either with atmospheric oxygen or carried out with 1% hydrogen peroxide solution as the oxidizing agent, with 10 parts by weight of hydrogen peroxide solution for 100 parts by weight of the emulsion were given. The respective coloring cream with or without an additional oxidizing agent was applied 90% gray, not specially treated human hair is applied and there for 30 minutes left. After the dyeing process had ended, the hair was washed out with a conventional shampoo and then dried. The dyeings obtained are shown in Table 1 below remove.
II.
II.
i'J.i'J.
§§
SjSj
ii
δι.·δι. ·
&&
i i
i
Fortsetzungcontinuation
Beispielexample
KupplerCoupler
m-Phenylendiaminm-phenylenediamine
2,4-Diaminoanisol m-Toluylendiamin
m-Aminophenol
Resorcin2,4-diaminoanisole m-tolylenediamine m-aminophenol
Resorcinol
l-Phenyl-3-aminopyrazolon-5 1-phenyl-3-aminopyrazolone-5
m-Phenylendiaminm-phenylenediamine
2,4-Diaminoanisol2,4-diaminoanisole
m-Aminophenolm-aminophenol
ResorcinResorcinol
m-Toluylendiaminm-tolylenediamine
l-Phenyl-3-aminopyrazolon-5
m-Phenylendiam i η1-phenyl-3-aminopyrazolone-5
m-phenylenediam i η
2,4-Diaminoanisol m-Toluylendiamin m-Aminophenol
Resorcin2,4-diaminoanisole m-tolylenediamine m-aminophenol
Resorcinol
l-Phenyl-3-aminopyrazolon-5 1-phenyl-3-aminopyrazolone-5
m-Phenylendiaminm-phenylenediamine
2,4-Diaminoanisol m-Toluylendiamin m-Aminophenol
Resorcin2,4-diaminoanisole m-tolylenediamine m-aminophenol
Resorcinol
l-Phenyl-3-aminopyrazolon-5 1-phenyl-3-aminopyrazolone-5
Zur Prüfung der toxikologischen und dermatologischen Eigenschaften von Tetraaminopyrimidinen wurden die nachstehend beschriebenen Untersuchungen durchgeführt Als Testsubstanz diente dabei 2-Dimethylamino-4,5,6-triaminopyrimidinsu]fat, die in Vergleich zu p-Phenylendiamin und p-Toluylendiaminsulfat gesetzt wurde. Dabei wurden die folgenden Ergebnisse erhalten.To examine the toxicological and dermatological properties of tetraaminopyrimidines were the investigations described below were carried out. The test substance was used 2-dimethylamino-4,5,6-triaminopyrimidinsu] fat compared to p-phenylenediamine and p-toluenediamine sulfate was set. The following results were obtained.
1. Akute Toxizität1. Acute toxicity
Die Prüfungen der allgemeinen Verträglichkeit wurden an männlichen weißen Mäusen des CF/W-68-Stammes durchgeführt. Das durchschnittliche Gewicht der Versuchtiere betrug 22 g. Die Verabfolgung der Prüfsubstanzen erfolgte einmal in steigenden Dosierungen mit der Schlundsonde. Es wurden pro Dosis 10 Mäuse eingesetzt. Das Applikationsvolumen betrug konstant 0,2 ccm/lOg Körpergewicht. Nach der 8tägigen Beobachtungszeit und nach Berechnung der Versuchsergebnisse nach dem Verfahren von Litchfield-Wilcoxon(J. Pharm. exptl. Then, 96 99-108 [1949]) wurden nachfolgende LD50- Werte gefunden.The general tolerance tests were carried out on male white mice of the CF / W-68 strain carried out. The average weight of the test animals was 22 g. The administration of the Test substances were carried out once in increasing doses with the gavage. There were 10 per dose Mice used. The application volume was a constant 0.2 ccm / 10 g body weight. After the 8 day Observation time and after calculation of the test results according to the method of Litchfield-Wilcoxon (J. Pharm. Exptl. Then, 96 99-108 [1949]) the following LD50 values were found.
2-Dimethylamino-4,5,6-triamino-2-dimethylamino-4,5,6-triamino-
pyrimidin-sulfat 555 mg/kgpyrimidine sulfate 555 mg / kg
p-Phenylendiamin 87 mg/kgp-phenylenediamine 87 mg / kg
p-Toluylendiaminsulf at 110 mg/kgp-Tolylenediamine sulf at 110 mg / kg
Als Lösungsmittel wurde Aqua dest. verwendet.Aqua dest was used as the solvent. used.
2. Hautverträglichkeitsprüfungen
an haarlosen Mäusen2. Skin compatibility tests
on hairless mice
Gruppen von jeweils 5 Tieren pro Präparat wurdenGroups of 5 animals per preparation were made
die Prüfsubstanzen in 5%igen wässerigen Ansätzen einmal täglich 14 Tage lang in kleinen Mengen auf die Rückenhaut aufgetragen. Während der Applikationszeit und bei Versuchsende waren alle Tiere reaktionslos.the test substances in 5% aqueous solutions once a day for 14 days in small amounts Applied back skin. All animals showed no reaction during the application period and at the end of the experiment.
3. Schleimhautverträglichkeitsprüfungen
am Kaninchenauge3. Mucosal compatibility tests
on the rabbit eye
Diese Prüfungen der lokalen Verträglichkeit wurden derart vorgenommen, daß kleine Mengen der 5%igen wässerigen Prüfsubstanzen Gruppen von Albino-Kaninchen einmal in den Bindehautsack eines AugesThese local compatibility tests were carried out so that small amounts of the 5% Aqueous test substances groups of albino rabbits once in the conjunctival sac of one eye
eingeträufelt wurden. Die Reaktionen der Augenschleimhäute wurden nach einem Punktschema von D r a i ζ e (Appraisal of the safety of chemicals in foods, drugs and domestics. Ass. of Food and Drug Official of the U.S, pp. 49-52 [1959]) 2,6,24 und 48 Stunden nachinstilled. The reactions of the mucous membranes were measured according to a point scheme of D r a i ζ e (Appraisal of the safety of chemicals in foods, drugs and domestics. Ass. Of Food and Drug Official of the U.S, pp. 49-52 [1959]) 2,6,24 and 48 hours after
der Applikation ausgewertet.. Es ergab sich dabei, daß p-Phenylendiamin zu einer geringgradigen Rötung und Exsudation der Conjunctiva führt, die 24 Ständen nach Einträufelung nicht mehr feststellbar ist. Die beiden anderen Prüfsubstanzen wurden reaktionslos vertragen.of the application evaluated .. It turned out that p-phenylenediamine leads to a slight reddening and exudation of the conjunctiva, which stalls 24 after Instillation can no longer be determined. The other two test substances were tolerated without reaction.
4. Haut- (Gewebe-) Verträglichkeitsprüfungen an weißen Mäusen nach einmaliger intracutaner Applikation verschiedener Konzentrationen der Testpräparate4. Skin (tissue) compatibility tests on white mice after a single intracutaneous application of various concentrations of the test preparations
Diese Prüfung der lokalen Verträglichkeit nach B a r a i 1 (J. Soc. Cosmet. Chemists Π, 241 [I960]) beruht auf der intracutanen Applikation von kleinen Mengen der Prüfsubstanz in steigenden Konzentrationen in die Bauchhaut der weißen Mäuse. Nach 24 Stunden werden die Versuchstiere getötet, die behandelten Hautstellen ausgeschnitten und getrocknet. Die Beurteilung der Hautschädigungen erfolgt nach einem Punktschema,This test of the local compatibility according to Bar a i 1 (J. Soc. Cosmet. Chemists Π, 241 [I960]) is based on the intracutaneous application of small amounts of the test substance in increasing concentrations in the White mouse abdominal skin. After 24 hours, the test animals are sacrificed, the treated areas of the skin cut out and dried. The skin damage is assessed according to a point scheme,
15 wobei die Durchblutung und andere Schädigungen der behandelten Haut Berücksichtigung finden. Da pro Präparat und pro Testkonzentration ein größeres Tierkollektiv von 10 Mäusen eingesetzt wurde, lassen sich nach der obigen Versuchsmethodik feinere Unterschiede hinsichtlich lokaler Verträglichkeit feststellen. Die Versuchsergebnisse sind der beigefügten Tabelle 2 zu entnehmen. 15 taking into account blood flow and other damage to the treated skin. Since a larger group of 10 mice was used per preparation and per test concentration, finer differences in terms of local tolerance can be determined using the above test method. The test results are shown in Table 2 attached.
Haut (Gewebe) Verträglichkeitsprüfung an weißen Mäusen nach intracutaner Applikation (Test nach Barail) Mittelwerte nach Beurteilung von jeweils 10 Versuchstieren pro Präparat bzw. pro KonzentrationSkin (tissue) compatibility test on white mice after intracutaneous application (test according to Barail) Average values after assessing 10 test animals per preparation or per concentration
p-Phenylendiaminp-phenylenediamine
2-Dimethylamino-2-dimethylamino
4,5,6-triamino-4,5,6-triamino-
pyrimidinsulfatpyrimidine sulfate
p-Toluylendiaminsulfat p-toluenediamine sulfate
Punkte bzw. Grad
der HautschädigungPoints or degrees
the skin damage
0,1 0,3 0,9 2,7 0,1 0,3 0,9 2,70.1 0.3 0.9 2.7 0.1 0.3 0.9 2.7
0,1 0,3 0,9 2,70.1 0.3 0.9 2.7
Konzentrationen der
Prüfsubstanzen in %Concentrations of
Test substances in%
Den vorstehend aufgeführten Prüfungsergebnissen ist zu entnehmen, daß sich 2-Dimethy!amino-4,5,6-triamino-pyrimidinsulfat hinsichtlich einer allgemeinen und lokalen Verträglichkeit unter den geprüften Entwicklersubstanzen am besten verhält. Neben diesen guten toxikologischen und dermatologischen Eigenschaften bringen die in den erfindungsgemäßen Haarfärbemittel einzusetzenden Tetraaminopyrimidine die weiteren Vorteile mit sich, daß die Entwicklung der Färbung bereits mit Luftsauerstoff erfolgen kann und zu einer außerordentlichen Variationsmöglichkeit an Farbtönen führt, die sich durch gute Licht-, Wasch- und Reibechtheitseigenschaften auszeichnen und mit Reduktionsmitteln wieder leicht abziehbar sind.The test results listed above show that 2-dimethylamino-4,5,6-triamino-pyrimidine sulfate with regard to general and local compatibility among the developer substances tested behaves best. In addition to these good toxicological and dermatological properties bring the tetraaminopyrimidines to be used in the hair dye according to the invention the other Advantages with it that the development of the color can already take place with atmospheric oxygen and to one extraordinary variation in color tones, which is characterized by good light, washing and They are characterized by rubbing fastness properties and can be easily peeled off again with reducing agents.
Claims (1)
Priority Applications (17)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19732359399 DE2359399C3 (en) | 1973-11-29 | 1973-11-29 | Hair dye |
DK576174A DK146374C (en) | 1973-11-29 | 1974-11-05 | HAIR PAINTING BASED ON OXIDATION COLORS |
SE7413878A SE414271B (en) | 1973-11-29 | 1974-11-05 | HARFER AGENTS BASED ON THE OXIDATION COMPONENTS CONTAINING TETRAAMINOPYRIMIDINES AS A DEVELOPING COMPONENT |
FI3228/74A FI58432C (en) | 1973-11-29 | 1974-11-05 | HAORFAERGNINGSMEDEL SOM BASERAR SIG PAO OXIDATIONSFAERGAEMNEN |
NL7415288.A NL165376C (en) | 1973-11-29 | 1974-11-22 | METHOD FOR PREPARING HAIR DYE SUBSTANCES, AND METHOD FOR DYEING HAIR |
CA214,601A CA1019243A (en) | 1973-11-29 | 1974-11-25 | Oxidation hair dyes based upon tetraaminopyrimidine developers |
BE150804A BE822542A (en) | 1973-11-29 | 1974-11-25 | HAIR DYES CONTAINING TETRAAMINOPYRIMIDINES |
AT949774A AT334542B (en) | 1973-11-29 | 1974-11-27 | HAIR COLORANT |
CH1579874A CH591242A5 (en) | 1973-11-29 | 1974-11-28 | |
BR9986/74A BR7409986A (en) | 1973-11-29 | 1974-11-28 | HAIR DYEING COMPOSITES |
FR7439050A FR2282858A1 (en) | 1973-11-29 | 1974-11-28 | HAIR DYES CONTAINING TETRAAMINOPYRIMIDINES |
JP49135964A JPS5910325B2 (en) | 1973-11-29 | 1974-11-28 | hair dye |
GB51533/74A GB1486576A (en) | 1973-11-29 | 1974-11-28 | Hair dyes |
IT29954/74A IT1049532B (en) | 1973-11-29 | 1974-11-28 | HAIR DYE |
AU75844/74A AU490961B2 (en) | 1974-11-28 | Hair dyes | |
AR256727A AR214855A1 (en) | 1973-11-29 | 1974-11-29 | COLORING COMPOSITIONS FOR HAIR BASED ON SUBSTITUTED PYRIMIDES |
US05/953,688 USRE30199E (en) | 1973-11-29 | 1978-10-23 | Oxidation hair dyes based upon tetraaminopyrimidine developers |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19732359399 DE2359399C3 (en) | 1973-11-29 | 1973-11-29 | Hair dye |
Publications (3)
Publication Number | Publication Date |
---|---|
DE2359399A1 DE2359399A1 (en) | 1975-06-12 |
DE2359399B2 true DE2359399B2 (en) | 1978-06-01 |
DE2359399C3 DE2359399C3 (en) | 1979-01-25 |
Family
ID=5899366
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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DE19732359399 Expired DE2359399C3 (en) | 1973-11-29 | 1973-11-29 | Hair dye |
Country Status (2)
Country | Link |
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BE (1) | BE822542A (en) |
DE (1) | DE2359399C3 (en) |
Families Citing this family (730)
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DE2626141A1 (en) * | 1976-06-11 | 1977-12-22 | Henkel Kgaa | Oxidation hair dyeing compsns. - contg. tetraamino-pyrimidine developers and amino-methoxy-quinoline yellow couplers |
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DE19535340A1 (en) * | 1995-09-22 | 1997-03-27 | Henkel Kgaa | An oxidation |
FR2740035B1 (en) | 1995-10-20 | 1997-11-28 | Oreal | KERATINIC FIBER DYEING PROCESS AND COMPOSITION IMPLEMENTED DURING THIS PROCESS |
FR2740036B1 (en) | 1995-10-20 | 1997-11-28 | Oreal | NOVEL OXIDIZING COMPOSITION AND NEW PROCESS FOR PERMANENT DEFORMATION OR HAIR DECOLORATION |
FR2742047B1 (en) | 1995-12-06 | 1998-01-16 | Oreal | KERATINIC FIBER DYEING COMPOSITIONS CONTAINING N-SUBSTITUTED DERIVATIVES OF 4-HYDROXY INDOLINE, NEW DERIVATIVES, THEIR SYNTHESIS METHOD, THEIR USE FOR DYEING, AND THE DYEING METHOD |
KR100296169B1 (en) | 1996-04-25 | 2001-08-07 | 조지안느 플로 | Method for dyeing keratin fibres with oxidation dye precursors and direct powder dies |
FR2752522B1 (en) * | 1996-08-26 | 1998-10-02 | Oreal | KERATINIC FIBER DYEING COMPOSITIONS CONTAINING PYRROLO- (3,2-D) -OXAZOLES; THEIR USE FOR DYEING AS COUPLERS, DYEING METHOD |
FR2752524B1 (en) | 1996-08-26 | 1998-10-02 | Oreal | COMPOSITIONS FOR DYEING KERATIN FIBERS CONTAINING S-OXIDE-THIAZOLO-AZOLES AND/OR S,S-DIOXIDE-THIAZOLO-AZOLES; THEIR USE FOR DYEING AS COUPLERS, DYEING PROCESS |
FR2767475A1 (en) * | 1997-08-25 | 1999-02-26 | Oreal | Oxidation hair dyes |
FR2767686B1 (en) | 1997-09-01 | 2004-12-17 | Oreal | COMPOSITION FOR OXIDATION DYEING OF KERATINIC FIBERS COMPRISING 2-CHLORO 6-METHYL 3-AMINOPHENOL AND TWO OXIDATION BASES, AND DYEING METHOD |
FR2767685B1 (en) | 1997-09-01 | 2004-12-17 | Oreal | COMPOSITION FOR OXIDATION DYEING OF KERATINIC FIBERS COMPRISING 2-CHLORO 6-METHYL 3-AMINOPHENOL AND AN OXIDATION BASE, AND DYEING METHOD |
FR2767687B1 (en) | 1997-09-01 | 1999-10-01 | Oreal | COMPOSITION FOR OXIDATION DYEING OF KERATINIC FIBERS COMPRISING 2-CHLORO 6-METHYL 3-AMINOPHENOL, AN OXIDATION BASE AND AN ADDITIONAL COUPLER, AND DYEING METHOD |
FR2768618B1 (en) * | 1997-09-23 | 1999-10-22 | Oreal | KERATINIC FIBER OXIDATION DYE COMPOSITION AND DYEING METHOD USING THE SAME |
FR2768617B1 (en) * | 1997-09-23 | 1999-10-22 | Oreal | KERATINIC FIBER OXIDATION DYE COMPOSITION AND DYEING METHOD USING THE SAME |
FR2768619B1 (en) * | 1997-09-23 | 1999-10-22 | Oreal | KERATINIC FIBER OXIDATION DYE COMPOSITION AND DYEING METHOD USING THE SAME |
FR2769213B1 (en) | 1997-10-03 | 1999-12-17 | Oreal | KERATIN FIBER DYEING COMPOSITION AND DYEING METHOD USING THE SAME |
FR2769222B1 (en) | 1997-10-03 | 1999-12-31 | Oreal | OXIDIZING COMPOSITION AND USES FOR DYING, FOR PERMANENT DEFORMATION OR FOR DECOLORATION OF KERATINIC FIBERS |
FR2769217B1 (en) | 1997-10-03 | 2000-03-17 | Oreal | OXIDIZING COMPOSITION AND USES FOR DYING, FOR PERMANENT DEFORMATION OR FOR DECOLORATION OF KERATINIC FIBERS |
FR2769220B1 (en) | 1997-10-03 | 2000-03-10 | Oreal | OXIDIZING COMPOSITION AND USES FOR DYING, FOR PERMANENT DEFORMATION OR FOR DECOLORATION OF KERATINIC FIBERS |
FR2769221B1 (en) | 1997-10-03 | 2000-01-14 | Oreal | OXIDIZING COMPOSITION AND USES FOR DYEING, PERMANENT DEFORMATION OR DECOLORATION OF KERATINIC FIBERS |
FR2769218B1 (en) | 1997-10-03 | 2000-03-10 | Oreal | OXIDIZING COMPOSITION AND USES FOR DYING, FOR PERMANENT DEFORMATION OR FOR DECOLORATION OF KERATINIC FIBERS |
FR2769214B1 (en) | 1997-10-03 | 1999-12-17 | Oreal | KERATIN FIBER DYEING COMPOSITION AND DYEING METHOD USING THE SAME |
FR2769211B1 (en) | 1997-10-03 | 1999-12-24 | Oreal | KERATIN FIBER DYEING COMPOSITION AND DYEING METHOD USING THE SAME |
FR2769223B1 (en) | 1997-10-03 | 2003-08-22 | Oreal | OXIDIZING COMPOSITION AND USES FOR DYING, FOR PERMANENT DEFORMATION OR FOR DECOLORATION OF KERATINIC FIBERS |
FR2769219B1 (en) | 1997-10-03 | 2000-03-10 | Oreal | OXIDIZING COMPOSITION AND USES FOR DYING, FOR PERMANENT DEFORMATION OR FOR DECOLORATION OF KERATINIC FIBERS |
FR2769215B1 (en) | 1997-10-03 | 1999-12-24 | Oreal | KERATIN FIBER DYEING COMPOSITION AND DYEING METHOD USING THE SAME |
FR2769216B1 (en) | 1997-10-03 | 1999-12-31 | Oreal | OXIDIZING COMPOSITION AND USES FOR DYEING, PERMANENT DEFORMATION OR DECOLORATION OF KERATINIC FIBERS |
FR2769210B1 (en) | 1997-10-03 | 2000-02-11 | Oreal | KERATIN FIBER DYEING COMPOSITION AND DYEING METHOD USING THE SAME |
FR2772267A1 (en) * | 1997-12-16 | 1999-06-18 | Oreal | Oxidation hair dye compositions |
DE19756682A1 (en) * | 1997-12-19 | 1999-06-24 | Henkel Kgaa | Oxidation hair dye compositions |
FR2773476B1 (en) | 1998-01-13 | 2001-02-23 | Oreal | TINCTORIAL COMPOSITION AND METHODS FOR DYEING KERATINIC FIBERS USING THE SAME |
FR2773475B1 (en) | 1998-01-13 | 2001-02-02 | Oreal | TINCTORIAL COMPOSITION AND METHODS FOR DYEING KERATINIC FIBERS USING THE SAME |
FR2773474B1 (en) | 1998-01-13 | 2002-10-11 | Oreal | TINCTORIAL COMPOSITION AND METHODS FOR DYEING KERATINIC FIBERS USING THE SAME |
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FR2786094B1 (en) | 1998-11-20 | 2001-01-12 | Oreal | KERATINIC FIBER OXIDATION DYE COMPOSITION AND DYEING METHOD USING THE SAME |
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FR2788774B1 (en) | 1999-01-21 | 2001-03-09 | Oreal | NOVEL CATIONIC DI-METHYLENEDIOXY-BENZENES, THEIR USE FOR OXIDATION DYEING OF KERATINIC FIBERS, TINCTORIAL COMPOSITIONS AND DYEING METHODS |
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DE19961910A1 (en) | 1999-12-20 | 2001-06-21 | Henkel Kgaa | Tablet for coloring keratinous fibers, especially human hair, contains alkalizing agent in addition to color precursor and oxidant in cosmetically acceptable medium |
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WO2023275193A1 (en) | 2021-06-30 | 2023-01-05 | L'oreal | Composition comprising at least one oxidation dye, 1,3-propanediol, at least one alkaline agent and at least one fatty substance |
FR3124705A1 (en) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprising propan-1,3-diol, at least one alkanolamine, at least one fatty substance and optionally at least one polyol |
FR3124709A1 (en) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprising at least one alkanolamine, one (meta)silicate, glycine and propane-1,3-diol. |
FR3127694B1 (en) | 2021-10-05 | 2024-01-12 | Oreal | compositions containing direct dyes to CONFER A color and A TONE to the hair |
FR3124732A1 (en) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprising shea, an alkyl(poly)glycoside, a polysaccharide and an alkaline agent and/or a dye |
FR3127131A1 (en) | 2021-09-17 | 2023-03-24 | L'oreal | Compositions to CONFER COLOR and TONE to the hair |
FR3124706A1 (en) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprising at least one alkanolamine, one (meta)silicate, glycine and one fatty acid. |
WO2023272610A1 (en) | 2021-06-30 | 2023-01-05 | L'oreal | Dye kit |
WO2023275211A1 (en) | 2021-06-30 | 2023-01-05 | L'oreal | Composition comprising at least one particular oxidation dye, at least one shea-derived fatty substance and at least one alkaline agent |
FR3124720A1 (en) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprising at least one particular coupler, at least one alkaline agent and at least one liquid fatty alcohol and at least one solid fatty alcohol. |
FR3124724A1 (en) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprising at least one alkyl(poly)glycoside, at least one fatty alcohol, at least one fatty acid, and at least one alkaline agent |
FR3124715A1 (en) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprising N,N-dicarboxymethyl glutamic acid, at least one fatty alcohol, at least one fatty acid, at least one polyol, at least one alkaline agent and optionally at least one colorant |
FR3124731A1 (en) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprising at least one particular oxidation coupler, at least one fatty substance derived from shea and at least one alkaline agent |
WO2023275197A1 (en) | 2021-06-30 | 2023-01-05 | L'oreal | Composition comprising at least one oxidation dye, at least one alkaline agent and at least one liquid fatty alcohol and at least one solid fatty alcohol |
FR3124725A1 (en) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprising at least one nonionic surfactant, propane-1,3-diol, at least one fatty substance, at least one alkaline agent and/or at least one coloring agent |
FR3124727A1 (en) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprising an alkanolamine, a (meta)silicate, glycine, a dye and a polysaccharide. |
CN117597104A (en) | 2021-06-30 | 2024-02-23 | 莱雅公司 | Combination for dyeing keratin fibres and use thereof |
FR3124716A1 (en) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprising at least one alkanolamine, one (meta)silicate, glycine and N,N-dicarboxymethyl glutamic acid. |
FR3124733A1 (en) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprising at least one oxidation base, at least an alkaline agent, and a fatty substance derived from shea |
FR3124714A1 (en) | 2021-06-30 | 2023-01-06 | L'oreal | Cosmetic composition comprising at least one alkyl(poly)glycoside, N,N-dicarboxymethyl glutamic acid, propane-1,3-diol, at least one fatty substance other than fatty acids, at least one alkaline agent and/or a coloring agent |
FR3124710A1 (en) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprising at least one particular coupler, propane-1,3-diol, at least one alkaline agent and at least one fatty substance. |
FR3124719A1 (en) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprising at least one particular coupler, at least one particular oxidation base, at least one fatty substance and at least one anionic polysaccharide. |
FR3124702A1 (en) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprising propane-1,3-diol and at least one fatty substance and one or more alkaline agents and/or one or more colorants. |
FR3124707A1 (en) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprising at least one particular base, propane-1,3-diol, at least one alkaline agent and at least one fatty substance. |
FR3124708A1 (en) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprising at least one particular base, at least one alkaline agent and at least one liquid fatty alcohol and at least one solid fatty alcohol. |
FR3127130A1 (en) | 2021-09-17 | 2023-03-24 | L'oreal | Compositions to CONFER COLOR and TONE to the hair |
US11707420B2 (en) | 2021-08-31 | 2023-07-25 | L'oreal | Compositions, kits, and methods for altering the color of hair |
FR3128120A1 (en) | 2021-10-19 | 2023-04-21 | L'oreal | compositions, kits and methods for modifying the color of keratinous fibers |
FR3127400A1 (en) | 2021-09-30 | 2023-03-31 | L'oreal | Process for dyeing and/or lightening keratin fibers comprising a step for dyeing and/or lightening keratin fibers and a step for treating the keratin fibers with a composition comprising at least one vegetable oil. |
FR3128377A1 (en) | 2021-10-26 | 2023-04-28 | L'oreal | Process for coloring and/or lightening keratin fibers |
FR3128636B1 (en) | 2021-10-29 | 2023-11-03 | Oreal | Composition comprising a particular oxidation coloring precursor and two particular acids. |
FR3128632A1 (en) | 2021-10-29 | 2023-05-05 | L'oreal | Composition comprising the combination of two particular oxidation coloring precursors and a fatty acid and glycerol ester. |
FR3128633A1 (en) | 2021-10-29 | 2023-05-05 | L'oreal | Composition comprising the combination of two particular oxidation coloring precursors and an amphoteric or zwitterionic surfactant. |
FR3128634A1 (en) | 2021-10-29 | 2023-05-05 | L'oreal | Composition comprising the combination of two particular oxidation coloring precursors and a fatty acid and glycerol ester. |
FR3128637A1 (en) | 2021-10-29 | 2023-05-05 | L'oreal | Composition comprising the combination of two particular oxidation coloring precursors and an amphoteric or zwitterionic surfactant. |
FR3128635A1 (en) | 2021-10-29 | 2023-05-05 | L'oreal | Composition comprising a particular oxidation coloring precursor and two particular acids. |
WO2023102011A1 (en) | 2021-11-30 | 2023-06-08 | Jasmine Martich | Compositions, methods, and kits for altering the color of hair |
FR3132635A1 (en) | 2022-02-17 | 2023-08-18 | L'oreal | compositions, methods and kits for modifying hair color |
US11839678B2 (en) | 2021-11-30 | 2023-12-12 | L'oreal | Compositions, methods, and kits for altering the color of hair |
WO2023106218A1 (en) | 2021-12-08 | 2023-06-15 | L'oreal | Composition for keratin fibers |
FR3131696A1 (en) | 2022-01-13 | 2023-07-14 | L'oreal | COMPOSITION FOR KERATIN FIBERS |
FR3130144A1 (en) | 2021-12-10 | 2023-06-16 | L'oreal | Composition comprising a particular oxidation coloring precursor, a particular amino silicone and a polyol |
FR3130150A1 (en) | 2021-12-10 | 2023-06-16 | L'oreal | Composition comprising a particular oxidation coloring precursor and a particular amino silicone |
FR3130142A1 (en) | 2021-12-10 | 2023-06-16 | L'oreal | Composition comprising two particular oxidation coloring precursors and a particular amino silicone |
FR3130151B1 (en) | 2021-12-10 | 2024-04-05 | Oreal | Composition comprising a particular oxidation coloring precursor, an oxyalkylenated fatty alcohol and a polysaccharide. |
FR3130152A1 (en) | 2021-12-10 | 2023-06-16 | L'oreal | Composition comprising two particular oxidation coloring precursors and a phosphoric surfactant. |
FR3130143A1 (en) | 2021-12-10 | 2023-06-16 | L'oreal | Composition comprising a particular oxidation coloring precursor and a particular amino silicone |
FR3130569A1 (en) | 2021-12-16 | 2023-06-23 | L'oreal | Composition for lightening keratin fibers and process for lightening keratin fibers using this composition |
FR3130572A1 (en) | 2021-12-16 | 2023-06-23 | L'oreal | Composition for lightening keratin fibers and process for lightening keratin fibers using this composition |
FR3130568B1 (en) | 2021-12-16 | 2024-02-16 | Oreal | Composition for lightening keratin fibers and process for lightening keratin fibers using this composition |
FR3130567B1 (en) | 2021-12-16 | 2024-02-16 | Oreal | Composition for lightening keratin fibers and process for lightening keratin fibers using this composition |
FR3130570A1 (en) | 2021-12-16 | 2023-06-23 | L'oreal | Composition for lightening keratin fibers and process for lightening keratin fibers using this composition |
FR3130571B1 (en) | 2021-12-16 | 2024-02-16 | Oreal | Composition for lightening keratin fibers and process for lightening keratin fibers using this composition |
FR3130582A1 (en) | 2021-12-22 | 2023-06-23 | L'oreal | Process for dyeing keratin fibers using a cosmetic composition comprising propane-1,3-diol and a coloring composition |
FR3130577A1 (en) | 2021-12-22 | 2023-06-23 | L'oreal | Composition comprising two polyols different from each other, an alkaline agent and a colorant |
FR3130580A1 (en) | 2021-12-22 | 2023-06-23 | L'oreal | Cosmetic composition comprising propane-1,3-diol, one or more alkaline agents, one or more associative cellulosic polymers and one or more colorants |
FR3130575A1 (en) | 2021-12-22 | 2023-06-23 | L'oreal | Cosmetic composition comprising propane-1,3-diol, one or more alkaline agents, one or more nonionic surfactants, one or more non-associative anionic acrylic polymers and one or more colorants |
FR3131695A1 (en) | 2022-01-12 | 2023-07-14 | L'oreal | Composition comprising at least one anionic surfactant, a particular silicone and a chemical oxidizing agent |
FR3131843A1 (en) | 2022-01-20 | 2023-07-21 | L'oreal | OXIDATION COLORING COMPOSITION COMPRISING AN ANIONIC SURFACTANT, AN AMPHOTERIC SURFACTANT SELECTED FROM BETAINE AND A METALLIC CATALYST |
FR3134719A1 (en) | 2022-04-26 | 2023-10-27 | L'oreal | compositions and methods for treating hair |
WO2023164307A1 (en) | 2022-02-28 | 2023-08-31 | Rughani Ronak | Compositions and methods for hair |
WO2023228870A1 (en) | 2022-05-25 | 2023-11-30 | L'oreal | Composition for coloring keratin fibers |
FR3137835A1 (en) | 2022-07-15 | 2024-01-19 | L'oreal | Composition for coloring keratinous fibers |
FR3136976A1 (en) | 2022-06-22 | 2023-12-29 | L'oreal | Composition for lightening keratin fibers and process for lightening keratin fibers using this composition |
FR3136967A1 (en) | 2022-06-22 | 2023-12-29 | L'oreal | Composition for lightening keratin fibers and process for lightening keratin fibers using this composition |
FR3136968A1 (en) | 2022-06-22 | 2023-12-29 | L'oreal | Composition for lightening keratin fibers and process for lightening keratin fibers using this composition |
FR3136966A1 (en) | 2022-06-22 | 2023-12-29 | L'oreal | Composition for lightening keratin fibers and process for lightening keratin fibers using this composition |
FR3136975A1 (en) | 2022-06-22 | 2023-12-29 | L'oreal | Composition for lightening keratin fibers and process for lightening keratin fibers using this composition |
FR3136971A1 (en) | 2022-06-22 | 2023-12-29 | L'oreal | Keratin fiber treatment process |
FR3136970A1 (en) | 2022-06-22 | 2023-12-29 | L'oreal | Keratin fiber treatment process |
FR3136973A1 (en) | 2022-06-22 | 2023-12-29 | L'oreal | Keratin fiber treatment process |
FR3136972A1 (en) | 2022-06-22 | 2023-12-29 | L'oreal | Composition for lightening keratin fibers and process for lightening keratin fibers using this composition |
FR3136974A1 (en) | 2022-06-22 | 2023-12-29 | L'oreal | Process for treating keratin fibers comprising a pre-treatment or post-treatment step |
FR3136979A1 (en) | 2022-06-22 | 2023-12-29 | L'oreal | Process for treating keratin fibers using a carnitine salt or carnitine derivative |
FR3139719A1 (en) | 2022-09-21 | 2024-03-22 | L'oreal | Compositions and methods for modifying hair color. |
WO2024030362A1 (en) | 2022-07-31 | 2024-02-08 | L'oreal | Compositions and methods for altering the color of hair |
FR3139991A1 (en) | 2022-09-23 | 2024-03-29 | L'oreal | Compositions and methods for modifying hair color. |
FR3139718A1 (en) | 2022-09-19 | 2024-03-22 | L'oreal | Compositions and methods for modifying hair color. |
FR3140542A1 (en) | 2022-10-11 | 2024-04-12 | L'oreal | Composition comprising an oxidation dye, an alkaline agent, a cationic galactomannan gum and a particular fatty acid |
FR3140541A1 (en) | 2022-10-11 | 2024-04-12 | L'oreal | Composition comprising an oxidation dye, an alkaline agent, a cationic galactomannan gum, a particular solid fatty acid and an anionic acrylic polymer |
-
1973
- 1973-11-29 DE DE19732359399 patent/DE2359399C3/en not_active Expired
-
1974
- 1974-11-25 BE BE150804A patent/BE822542A/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
DE2359399C3 (en) | 1979-01-25 |
DE2359399A1 (en) | 1975-06-12 |
BE822542A (en) | 1975-05-26 |
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