WO2009013779A2 - Colorants directs photostables et leur procédé de production - Google Patents

Colorants directs photostables et leur procédé de production Download PDF

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Publication number
WO2009013779A2
WO2009013779A2 PCT/IT2008/000494 IT2008000494W WO2009013779A2 WO 2009013779 A2 WO2009013779 A2 WO 2009013779A2 IT 2008000494 W IT2008000494 W IT 2008000494W WO 2009013779 A2 WO2009013779 A2 WO 2009013779A2
Authority
WO
WIPO (PCT)
Prior art keywords
dye
microspheres
dyes
polymer
dye composition
Prior art date
Application number
PCT/IT2008/000494
Other languages
English (en)
Other versions
WO2009013779A3 (fr
Inventor
Cecilia Anselmi
Marisanna Centini
Simona Lupia
Original Assignee
Universita' Degli Studi Di Siena
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 Universita' Degli Studi Di Siena filed Critical Universita' Degli Studi Di Siena
Publication of WO2009013779A2 publication Critical patent/WO2009013779A2/fr
Publication of WO2009013779A3 publication Critical patent/WO2009013779A3/fr

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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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0097—Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with 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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/11—Encapsulated compositions
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0004—Coated particulate pigments or dyes
    • C09B67/0005—Coated particulate pigments or dyes the pigments being nanoparticles
    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0004—Coated particulate pigments or dyes
    • C09B67/0008—Coated particulate pigments or dyes with organic coatings
    • C09B67/0013—Coated particulate pigments or dyes with organic coatings with polymeric coatings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/42—Colour properties
    • A61K2800/43—Pigments; Dyes
    • A61K2800/432—Direct dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers

Definitions

  • the invention concerns improvements in hair dyes and more specifically though not exclusively in semi-permanent hair dyes. More generally, the present invention concerns dyes suitable for cosmetic applications and dye compounds for compositions useful in cosmetic applications. Background art
  • colorants or dyes usable in cosmetic applications are defined by local laws and regulations. For example, colorants or dyes approved by Italian law are listed, according to their Color Index classification, in Annex IV to Law 713/86 and subsequent updates. They fall into four categories of application according to their toxicological and physical properties:
  • the "permanent hair dyes” allow a durable change of the natural hair colour, through an oxidation reaction carried out with colorless bases and therefore not listed in Annex IV but in Annex III of the above mentioned Italian Law. As a result of such reaction the oxidized molecules on the hair are transformed into colored compounds, the so-called oxidative dyes.
  • This coloration is resistant to shampooing and other external factors, but is sensible to light, that can modify the color, and can often cause contact allergic dermatitis, due mainly to compounds such as like para- phenylenediamine, nitro-ortho- phenylenediamine and nitro-para- phenylenediamine used in the oxidative process.
  • This coloration resists to 4-5 shampooing, with slow and uniform bleaching, because the dyes used have a good affinity for hair keratin, are resistant to the light (a function of the type of molecule used), and to the mechanical action of the comb, therefore the color is progressively reduced after repetitive washings.
  • These products are useful to partially mask white hairs, add highlights to a natural color or to make grey hair more attractive.
  • Semi-permanent coloration does not need any preliminary or simultaneous modification of the keratin or oxidation processes of the melanin of the hair.
  • the dyes used in semi-permanent colorations are mainly nitroanilines, nitrophenylenediamines, nitroaminophenols, azo- e anthra-quinones derivatives.
  • the “temporary hair dyes”, also called “highlights”, provide only temporary changes and add light and brightness, while keeping the natural colour; this provides only a slight change in the natural hair color. In this case the colour can be removed during the first shampoo.
  • the temporary dyes can therefore only improve or correct an existing shade, add a slight shade or confer improved brightness.
  • the dyes employed act by depositing colorants on the cuticle of the hair without being absorbed, due to their high molecular weight, and can be easily removed with the first shampooing.
  • keratin fibers contained in a formulation of a product without oxidative agents. Also in this case the coloring substances are not encapsulated in delivery systems.
  • oxidative hair dyes have been encapsulated in microcapsules, as reported in WO-A-2006/24334 ("Microencapsulated oxidative hair dyes”), but all the formulations disclosed therein contain oxidative agents.
  • Microcapsules containing water soluble direct dyes have been disclosed in US-A-2006/171 ,909 ("Cosmetic compositions comprising colorants with low free dye") to be used on the skin, hair and nails.
  • the present invention concerns substantive photostable dyes for semipermanent or direct hair coloring.
  • this invention concerns microencapsulated dyes and dye compositions using said microencapsulated dyes.
  • the dye is microencapsulated in substantive microspheres, i.e. microparticles, which are stable to light, long lasting and without negative effects, for example as far as bio-compatibility and safety are concerned.
  • a substantive microsphere is one which forms a non-covalent bond with keratin or a keratinaceous substance, such as for example hair, nails or other human tissues containing keratin.
  • the microspheres are preferably cationic microspheres.
  • the dye-encapsulating microspheres are suitable for direct hair coloring. Moreover, they can give a uniform, long lasting, coloration stable to UV radiation and safe for the skin. Encapsulation or micro-encapsulation of dyes in the microspheres protects the dye from damages and alterations induced e.g. by UV or visible light radiation. The substantive nature of the microspheres allows the dye to be indirectly bound to the hairs or other keratinaceous substances.
  • the present invention also concerns methods for obtaining substantive microspheres for direct hair coloration or for other uses, specifically cosmetic uses, such as for the production of dye compositions for nails, skin and other keratin-containing substances.
  • the method of the invention provides for the manufacturing of cationic substantive microspheres containing direct, i.e. semi-permanent, hair dyes.
  • the microspheres are manufactured by solvent evaporation
  • the microspheres are manufactured by spray drying technique.
  • the substantive microspheres contain dyes for the above mentioned applications, where a methacrylic polymer (as EUDRAGIT ® RS 12,5, RS 3OD, RS 100, RS PO, RL 12,5, RL
  • 3OD, RL 100, RL PO, RD 100, E12.5, E100, EPO) or any natural and synthetic cationic polymers and the dye are dispersed in a volatile solvent and then the obtained phase is emulsified with a continuous dispersing phase. After evaporation of the solvent, the microspheres thus obtained are harvested by filtration, washed and finally dried under vacuum.
  • a stabilizing agent can be added to the emulsion to avoid droplet coalescence.
  • a cationic polymer e.g. a methacrylic polymer
  • stearate magnesium and dye are dispersed in an organic solvent (for example acetone).
  • the organic phase thus obtained is dispersed under stirring in a lipophilic solvent (for example mineral oil) or immiscible with the dispersed phase containing the cationic polymer.
  • a lipophilic solvent for example mineral oil
  • a further subject of the invention is a process for the production of substantive microspheres containing dyes, wherein the polymer (e.g. a cationic polymer) and the dye are dispersed in a suitable solvent and the solution or dispersion obtained is nebulized using a spray-dryer.
  • the temperature is suitably set based on the solvent used.
  • the dye can be selected from the group including: HC RED n. 3; BASIC RED 51 , HC BLUE n. 2, BASIC BROWN 16 and BASIC BROWN 17 and all suitable dyes for direct hair coloring, natural or/and synthetic dyes included or not included in Annexes in accordance with EU Cosmetic Directive, excluded dyes listed in Annex Il (forbidden substances).
  • Substantive cationic microspheres have been obtained, resistant to light and thermostable, that confer to the hair a uniform and long lasting coloration.
  • microencapsulated dyes in these cationic microspheres are stable and preserve their chemical-physical, organoleptic and functional properties, that make them suitable for their use.
  • microspheres according to the invention easily bind to the hair, having high physical-chemical affinity for keratin ("substantive" microspheres).
  • Figs. 1-6 show scanning electron microscope images of microspheres obtained by an emulsification/evaporation method
  • Figs. 6-10 show scanning electron microscope images of microspheres obtained by the solvent evaporation technique and spray- drying.
  • microparticles microspheres have been prepared by two methods:- the solvent evaporation (emulsification/evaporation) method and the spray- drying method.
  • a natural or synthetic substantive polymer e.g. a cationic polymer and more specifically a methacrylic polymer, for instance
  • a dye or a dyes mixture are dispersed in a volatile solvent and then the obtained (dispersed) phase A is emulsified with a continuous (dispersing) phase B. Since the two phases are immiscible, a stable emulsion is formed thanks to the presence of a droplets stabilizer preventing droplets coalescence during solvent evaporation. After evaporation of the solvent, the microspheres are harvested by filtration, washed a suitable number of times, typically 4-5 times with a suitable solvent and finally dried under vacuum.
  • a natural or synthetic substantive polymer e.g. a cationic polymer and more specifically a methacrylic polymer, for instance
  • a dye or a dyes mixture are dispersed in a volatile solvent and then the obtained (dispersed) phase A is emulsified with a continuous (dispersing) phase
  • Example 1 Some examples of this preparation method are set forth here below: Example 1
  • LOWENSTEIN & Sons, Inc. New York - U.S.A.
  • concentrations from about 1% to about 90% preferably from about 10% to about 50%
  • an organic solvent acetone
  • the organic phase A is dispersed under stirring in a phase B, constituted by a lipophilic solvent (for example mineral oil or paraffin oil).
  • a lipophilic solvent for example mineral oil or paraffin oil.
  • the dispersing phase B must not dissolve the polymer and must be immiscible with the dispersed phase A.
  • the system is emulsified with a turboemulsifier at speeds from about
  • Example 2 The same preparation as Example 1 using BASIC RED 51 (2[(4-
  • Example 3 The same preparation as Example 1 using HC BLUE No. 2 (N 1 , N 4 , N 4 - tri(hydroxyethyl)-2-nitro-p-phenylenediamine) dye supplied by SIGMA- ALDRICH (Milano - ITALY) and analogous conditions.
  • Example 4 The same preparation as Example 1 using HC BLUE No. 2 (N 1 , N 4 , N 4 - tri(hydroxyethyl)-2-nitro-p-phenylenediamine) dye supplied by SIGMA- ALDRICH (Milano - ITALY) and analogous conditions.
  • Example 5 The same preparation as Example 1 using BASIC BROWN 16 (8-[(4- aminophenyl)diazenyl]-7-hydroxy-N,N,N-trimethyl-naphthalen-2 ammonium chloride) dye supplied by LCW SENSIENT COSMETIC TECHNOLOGIES (Saint Ouen L'Aumone - France) and analogous conditions.
  • BASIC BROWN 16 (8-[(4- aminophenyl)diazenyl]-7-hydroxy-N,N,N-trimethyl-naphthalen-2 ammonium chloride) dye supplied by LCW SENSIENT COSMETIC TECHNOLOGIES ( Saint Ouen L'Aumone - France) and analogous conditions.
  • BASIC BROWN 16 8-[(4- aminophenyl)diazenyl]-7-hydroxy-N,N,N-trimethyl-naphthalen-2 ammonium chloride
  • the second method for obtaining the microspheres is the so-called spray drying method.
  • Said method is based on nebulizing a polymer solution or dispersion containing the dye or a dyes mixture through a dessiccating chamber of a spry-dryer.
  • the solvent is rapidly evaporated by a stream of heated air transforming the small droplets in solid microparticles.
  • Microparticles obtained are usually organic solvent free with respect to other preparation methods.
  • the dispersion obtained is nebulized at temperature higher than that of solvent boiling point.
  • microspheres containing the dye are obtained after evaporation of organic solvent.
  • Example 8 The same preparation as Example 6 using Basic Brown 16 (8-[(4- aminophenyl)diazenyl]-7-hydroxy-N,N,N-trimethyl-naphthalen-2 ammonium chloride) dye supplied by LCW SENSIENT COSMETIC TECHNOLOGIES (Saint Ouen L'Aumone - France) and analogous conditions. Morphological and size analysis - Substantivity evaluation The microspheres have been observed under a scanning electronic microscope (SEM) in order to determine their morphology and particle size.
  • SEM scanning electronic microscope
  • the attached figures show some of such morphologies with a relative dimensional range (0.1-500 micrometers, preferably from about 1 to about 150 micrometers, more preferably from about 1 to about 50 micrometers) _ _
  • Figs. 1-6 show microspheres prepared by emulsification/evaporation method and Figs. 5-10 show microspheres prepared by spray-drying method.
  • the microspheres prepared by the solvent evaporation technique and spray-drying have been analyzed spectrophotometrically to determine their loading (the dye percentage obtained).
  • the data obtained show a good encapsulation efficacy (between 50% and 95 %) for all dyes tested.
  • Substantivity of the microspheres i.e. the capability of the microspheres to bind to keratin or keratinaceous substances, has been measured to hair keratin as described here below.
  • Natural hair pigmented with different colors has been used as a substrate.
  • the residual dye percentage on the hair has been evaluated spectrophotometrically: a) after application of a lipophilic or hydrophilic gel containing the dye free or included in the microspheres; b) after application of an aqueous solution or dispersion of dye free or included in microspheres followed by five washing with shampooing.
  • Spectrophotometrical analyses, performed on native hair have shown that, under the experimental conditions, the hair does not release substances able to interfer with the measurements. Substantivity evaluation using method a)
  • HC RED No 3 dye is about 68% in the case of free dye, while the dye microencapsulated in the microspheres showed a substantivity of about 94%.
  • Substantivitv evaluation using method b) The results have shown that substantivity in general can vary from
  • the residual amount of dye on the hair is from about 1 to about 40 times preferably from about 1 to about 10 times higher when using dyes microencapsulated in microspheres with respect to free dye.
  • the substantivity of HC RED No. 3 dye, evaluated after 15 minutes of contact of the hair with the aqueous dye solution, is 35%, while microencapsulated dye in microspheres showed a substantivity of 70%.
  • the free dye stability has been compared with that of microencapsulated dye irradiating the samples with a solar simulator equipped of Xenon lamp and irradiating for to 10, 20 and 30 MED (corresponding to 300, 600 and 900 mJ/cm 2 ).
  • the spectrophotometrical data obtained from the analysis of the samples indicate (during irradiation time corresponding with the maximum irradiated power) that the free dye is photodegraded from 10% to 98% according to case, while only 1.5% to 9% of the same dye was degraded when microencapsulated in the microparticle system. Therefore as a result of microencapsulation the degradation of dye is very low and consequently there is no discoloration of semi-permanent coloring for exposure of hair to UV ray.
  • the micro-particles i.e.
  • microspheres according to the present invention can be included in various cosmetic vehicles suitable for application on the hair (mono-, bi-, three- phase systems): powders, lotions, gels, shampoos-in formulations, mousses, oils, emulsions O/W, W/O, W/S, multiple emulsions, paste, spray, etc. They could be further included in hair cosmetic formulations providing more durable effects. They consist of the conventional semipermanent dyes blended with oxidative dye precursors, which in conjunction with oxidant produces longer lasting color moieties. Such products are occasionally referred to as "demipermanents". Often included in the semipermanent category are also the vegetable dyes that are permitted to be used in EU.
  • microspheres according to the invention can be foreseen in compositions, such as cosmetic compositions, for skin and nail applications, choosing suitable dyes allowed under current regulations for those specific applications.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nanotechnology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Composite Materials (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Materials Engineering (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Cosmetics (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

Abstract

Cette invention concerne un colorant direct et photostable approprié pour des applications cosmétiques et obtenu en encapsulant un colorant dans des microsphères directes, qui se lie à la kératine. Les microsphères protègent le colorant de l'effet préjudiciable de la lumière et des UV, et garantissent la fixation du colorant au cheveu ou à toute autre substance à kératine.
PCT/IT2008/000494 2007-07-24 2008-07-22 Colorants directs photostables et leur procédé de production WO2009013779A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITFI2007A000168 2007-07-24
ITFI20070168 IT1377153B (it) 2007-07-24 2007-07-24 "coloranti sostantivi fotostabili per la colorazione semipermanente dei capelli"

Publications (2)

Publication Number Publication Date
WO2009013779A2 true WO2009013779A2 (fr) 2009-01-29
WO2009013779A3 WO2009013779A3 (fr) 2009-07-30

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Application Number Title Priority Date Filing Date
PCT/IT2008/000494 WO2009013779A2 (fr) 2007-07-24 2008-07-22 Colorants directs photostables et leur procédé de production

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IT (1) IT1377153B (fr)
WO (1) WO2009013779A2 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010069855A1 (fr) * 2008-12-19 2010-06-24 Henkel Ag & Co. Kgaa Agents de coloration enrobés
EP2394630A3 (fr) * 2010-06-11 2015-06-03 ROVI Cosmetics International GmbH Composition cosmétique destinée à la coloration des cheveux à l'aide d'un colorant capillaire directe et d'un système de véhicule constitué de vésicules lipidiques
EP2394629A3 (fr) * 2010-06-11 2015-06-24 ROVI Cosmetics International GmbH Composition cosmétique destinée à la coloration des cheveux à l'aide d'un colorant capillaire directe et d'un système de véhicule constitué de polysaccharides

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19914927A1 (de) * 1999-04-01 2000-10-05 Schwarzkopf Gmbh Hans Pflegende Wirkstoffkombination in Haarbehandlungsmitteln
DE19962872A1 (de) * 1999-12-24 2001-06-28 Henkel Kgaa Mittel zum Färben von keratinhaltigen Fasern
WO2002000994A1 (fr) * 2000-06-28 2002-01-03 The Procter & Gamble Company Composition pour le traitement de tissus
WO2002090445A1 (fr) * 2001-05-04 2002-11-14 Ciba Specialty Chemicals Water Treatments Limited Colorants encapsules dans une matrice polymere
US20040161468A1 (en) * 2002-12-04 2004-08-19 L'oreal Stabilization of aromatic active principles using aromatic polymers
DE102004037105A1 (de) * 2004-07-30 2005-01-13 Wella Ag Mehrkomponenten-Kit und Verfahren zum Färben von Keratinfasern
WO2005084618A1 (fr) * 2004-03-03 2005-09-15 Henkel Kommanditgesellschaft Auf Aktien Produit de traitement de fibres de keratine
US20060162097A1 (en) * 2003-10-10 2006-07-27 Juergen Schmenger Dye-containing pellets for dyeing keratin fibres
EP1820487A1 (fr) * 2006-02-13 2007-08-22 Wella Aktiengesellschaft Pastilles contenant un colorant et leur utilisation

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19914927A1 (de) * 1999-04-01 2000-10-05 Schwarzkopf Gmbh Hans Pflegende Wirkstoffkombination in Haarbehandlungsmitteln
DE19962872A1 (de) * 1999-12-24 2001-06-28 Henkel Kgaa Mittel zum Färben von keratinhaltigen Fasern
WO2002000994A1 (fr) * 2000-06-28 2002-01-03 The Procter & Gamble Company Composition pour le traitement de tissus
WO2002090445A1 (fr) * 2001-05-04 2002-11-14 Ciba Specialty Chemicals Water Treatments Limited Colorants encapsules dans une matrice polymere
US20040161468A1 (en) * 2002-12-04 2004-08-19 L'oreal Stabilization of aromatic active principles using aromatic polymers
US20060162097A1 (en) * 2003-10-10 2006-07-27 Juergen Schmenger Dye-containing pellets for dyeing keratin fibres
WO2005084618A1 (fr) * 2004-03-03 2005-09-15 Henkel Kommanditgesellschaft Auf Aktien Produit de traitement de fibres de keratine
DE102004037105A1 (de) * 2004-07-30 2005-01-13 Wella Ag Mehrkomponenten-Kit und Verfahren zum Färben von Keratinfasern
EP1820487A1 (fr) * 2006-02-13 2007-08-22 Wella Aktiengesellschaft Pastilles contenant un colorant et leur utilisation

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010069855A1 (fr) * 2008-12-19 2010-06-24 Henkel Ag & Co. Kgaa Agents de coloration enrobés
US8110010B2 (en) 2008-12-19 2012-02-07 Henkel Ag & Co. Kgaa Coated coloring agents
EP2394630A3 (fr) * 2010-06-11 2015-06-03 ROVI Cosmetics International GmbH Composition cosmétique destinée à la coloration des cheveux à l'aide d'un colorant capillaire directe et d'un système de véhicule constitué de vésicules lipidiques
EP2394629A3 (fr) * 2010-06-11 2015-06-24 ROVI Cosmetics International GmbH Composition cosmétique destinée à la coloration des cheveux à l'aide d'un colorant capillaire directe et d'un système de véhicule constitué de polysaccharides

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Publication number Publication date
IT1377153B (it) 2010-07-12
WO2009013779A3 (fr) 2009-07-30
ITFI20070168A1 (it) 2009-01-25

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