EP0288553A4 - Composition used in permanent alteration of hair color - Google Patents

Composition used in permanent alteration of hair color

Info

Publication number
EP0288553A4
EP0288553A4 EP19870907847 EP87907847A EP0288553A4 EP 0288553 A4 EP0288553 A4 EP 0288553A4 EP 19870907847 EP19870907847 EP 19870907847 EP 87907847 A EP87907847 A EP 87907847A EP 0288553 A4 EP0288553 A4 EP 0288553A4
Authority
EP
European Patent Office
Prior art keywords
hair
composition
quaternized amino
amino lactam
lactam
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.)
Withdrawn
Application number
EP19870907847
Other languages
English (en)
Other versions
EP0288553A1 (fr
Inventor
Michael W. Helioff
Carmen D. Bires
Robert B. Login
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
GAF Corp
Original Assignee
GAF Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US06/922,923 external-priority patent/US4732990A/en
Priority claimed from US07/060,284 external-priority patent/US4834767A/en
Application filed by GAF Corp filed Critical GAF Corp
Publication of EP0288553A1 publication Critical patent/EP0288553A1/fr
Publication of EP0288553A4 publication Critical patent/EP0288553A4/en
Withdrawn legal-status Critical Current

Links

Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
    • 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
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • 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
    • A61Q5/08—Preparations for bleaching the hair
    • 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

Definitions

  • the invention relates to an aqueous composition containing a stable conditioning, softening and penetrating agent for hair undergoing treatment with a color altering formulation.
  • the invention relates to an agent which enhances the dissolution of melanin and promotes penetration of an oxidation dye intermediate into a hair follicle.
  • the invention relates to an additive for a hair bleaching composition and, in yet another aspect an additive for a permanent hair coloring shampoo composition.
  • the main coloring component of hair is a dark pigment, melanin, which occurs as granules embedded in the hair cortex.
  • the aim of bleaching is to decolorize selectively the natural pigments or applied pigments in the hair with minimal damage to the hair matrix.
  • the color changes to lighter and lighter shades depending upon the amount of melanin granules dissolved and removed from the hair fiber.
  • Hydrogen peroxide is the leading solvent for melanin used in the bleaching process; however, along with melanin removal, the peroxide reacts with keratin to cause loss of tensile properties and damage to the hair.
  • bleaching occurs in two steps: (1) initial solubilization of the color granules, and (2) decolorization of the dark brown solubilized pigment.
  • the reaction between melano-protein and hydrogen peroxide is confined mainly to the protein-combined cystene residues which are subsequently converted to combined cysteic acid.
  • the solubilization of the melanin granules is connected with the splitting of the disulfide bridges in the melano protein and it is likely that the disulfide bridge may be the stabilizing factor in melanin, as it is in keratins.
  • the bleaching process can be halted at any point or can be permitted to continue to a light blonde or platinum shade.
  • the latter provides a good background for a variety of tints which can be obtained by a subsequent coloring step.
  • Such bleaching and coloring combination is known as a double process coloring and causes hair damage by promoting porosity, brittleness, loss of tensile strength and dryness.
  • Permanent hair colorants involve the use of oxidation dye intermediates which are colorless substances but which, when mixed with oxidizing agents just prior to use, produce color by a process of oxidative condensation. More specifically, the intermediates, in the presence of an oxidant, couple with another oxidation dye intermediate molecule to form a large fused ring color compound within the hair fiber. Since the fused ring product is too large to penetrate the hair fiber, it is essential that good penetration is achieved by the precursor intermediate. The oxidation dye process engenders many changes in the chemical and cosmetic characteristics of the hair which are undesirable. Specifically, the effect of alkali swelling of the hair fiber leads to loss of tensile strength, flexibility and promotes a porous, dry appearance.
  • the oxidation dye intermediates often cause skin sensitivity and reddening. Still further, the color imparted on processed hair is often non-uniform since the preprocessed sections, have higher porosity and absorb the interemediate at a faster rate than virign growth which is more resistant to absorption.
  • Certain quaternized amine compounds and polymeric amines as disclosed in U.S. Patent 4,532,127 and U.S. Patent 4,579,732 have been developed to overcome some of the above problems. However these basic compounds have not been found to be completely satisfactory since they react with anionic components which are commonly present in hair colori ng or bleaching composi tions . Thi s reactivity causes undesirable alterations in the shade desired.
  • the amino groups react with hydrogen peroxide to form nitrogen oxides, thus increasing the effective amount of peroxide which must be employed in bleaching compositions. Since peroxides are known to have a drying effect on hair, it is desirable to use as little as possible to obtain the desired effect. Further the relatively high viscosity of the polymeric compounds together with the normal variation in molecular weiqht of the polymer chains in the product lead to formulation problems in reproducability of product quality and in storage of the product over extended periods. In addition the large molecular size of the polymeric products prevents their penetration into the hair fiber and instead forms a coating over the hair, which may develop tack under conditions of high humidity. Finally, many hair dye and bleaching compositions produce a disagreeable odor which the prior quaternized amino compounds do not mask.
  • a quaternized amino lactam which is incorporated into a permanent hair color altering formulation at a concentration of between about 0.01 to about 12 wt. %, preferably between about 0.5 and about 7.5 wt. % based on total weight of the treating formulation.
  • the lactams of the present invention are defined by the structure
  • m is an integer having a value of from 1 to 4;
  • R is alkylene having from 3 to 8 carbon atoms and is optionally substituted with C 1 to C 4 alkyl;
  • R 1 , R 2 and R 3 are each independently selected from the group of alkyl, alkyl oxide, alkylhydroxy, alkoxy, aryl, aralkyl, alkaryl, and alkyl amidoalkyl radicals, said groups each having from 1 to 30 carbon atoms and at least one of R 1 , R 2 and R 3 is a radical having from 8 to 30 carbon atoms;
  • X- is a chloride, bromide or iodide anion, preferably a chloride anion.
  • lactams having the formula
  • pyrrolidones wherein at least one of R 2 and R 3 is octadecyl, hexadecyl, tetradecyl, hydrogenated tallow or coco and wherein the other of R 2 and R 3 is methyl or the same as R 3 .
  • R 3 is hexadecyl or octadecyl which are employed in a concentration of between about 0.75 and about 5.0 wt. %.
  • the present lactams pyrrolidones are beneficially incorporated into the color altering formulation just before use.
  • formulation includes a cream, a gel, an emulsion or a watery liquid or detergent solution.
  • the present lactams can be used individually or in admixtures and can be added to any of the commercial hair bleaching or oxidation dye intermediate formulations or compositions containing an oxidation dye intermediate including a permanent shampoo tint, a permanent hair dye, hair bleach, hair blanch or hair dye removal preparation for home or professional use.
  • an oxidation dye intermediate including a permanent shampoo tint, a permanent hair dye, hair bleach, hair blanch or hair dye removal preparation for home or professional use.
  • color altering preparations may be made up using the components normally included in preparations currently marketed and the lactams of this invention added to improve properties and minimize hair damage.
  • the permanent hair dye formulations of this invention are those employed for changing the color of hair, covering up white hair, shading the hair after lightening or simultaneous bleaching and dyeing or double process blonding to provide color alteration of long color durability.
  • the permanent dye formulations of this invention conventionally include an oxidation dye intermediate such as an analog or a derivative of a phenylene diamine, an aminophenol, a phenol or naphthol which, upon oxidation couples with itself or another analog or derivative of phenylene diamine to form a large fused ring compound having at least one unsaturated chromophoric bond within the hair fiber.
  • the color developed from the colorless intermediate depends on the substituents or terminal groups of the diamine, for example, such groups as an aromatic amine or phenol, an aromatic nitro group or trace amounts of heavy metal. Other factors which alter the shade of the dyed hair include concentration, alkaninity, base composition and the combination of intermediates involved in the oxidation reaction.
  • the dyeing or bleaching of hair generally requires from about 10 to about 40 minutes of processing time.
  • Use of the present lactams can reduce processing time by at least 10%.
  • Table I provides a representative group of dye intermediates, color couplers and modifiers employed to obtain specific hair shades. Also, any of the dyes disclosed in U.S. Patent 4,532,127 are suitably employed in this invention.
  • color modifiers or couplers include m-diamines, m-amino phenols, polyhydroxy phenols, which are also stabilizers and antioxidants, and naphthols.
  • the later are often used as secondary dye intermediates in the formulation.
  • Pyridine derivatives have also been suggested for use as a dye intermediate in place of phenylene diamines.
  • direct dyes can be added to the formulations to provide color highlights.
  • the color vehicle for the dye intermediates is employed at a pH usually between about 9 and 11 which can be adjusted with ammonium hydroxide to the desired level of alkalinity.
  • the ammonium hydroxide base is preferred since ammonia assists in swelling the hair fiber and by being easily removed.
  • the color vehicle is an aqueous solution of soap or synthetic detergent which provides wetting and penetration of the dye intermediate.
  • Ammonium oleate, alkanol amides and shampoo detergents such as fatty alkyl sulfates, fatty acid polypeptide condensates and oxyethylated fatty alcohols are most commonly employed.
  • formulations may also include interemediate solubility aids such as propylene glycol, ethyl alcohol or isopropyl alcohol and conditioners such as glycerol, lanolin, oleyl alcohol, cetyl alcohol, etc. and antioxidants such as a sulfite, primarily sodium sulfite or bisulfite, and thioglycolic acid which are usually included to prevent premature oxidation.
  • interemediate solubility aids such as propylene glycol, ethyl alcohol or isopropyl alcohol and conditioners such as glycerol, lanolin, oleyl alcohol, cetyl alcohol, etc.
  • antioxidants such as a sulfite, primarily sodium sulfite or bisulfite, and thioglycolic acid which are usually included to prevent premature oxidation.
  • lactams to this formulation obviates the need for other conditioners, promotes penetration of the intermediate into the hair fiber particularly in the areas of new growth, substantially reduces skin sensitization, promotes hair fiber swelling and results in a more uniform distribution of color while giving the hair a soft, silky, conditioned texture after processing.
  • the lactam moiety, particularly the pyrrolidonyl moiety of the present compounds exerts a stabilizing effect on the quaternized amino group so that the present compounds do not react with peroxides or anionic components. This stabilizing effect enables the use of smaller amounts of these components to achieve the desired effect.
  • the oxidation dye intermediate formulation is applied to the hair with a oxidation dye developer.
  • the developer is an oxidant mixed with the intermediate formulation just before application and is usually applied in equal parts with the intermediate formulation; although when hydrogen peroxide is used as the developer, between about 1.5 and about 2 parts peroxide per part of intermediate can be used to cause bleaching and coloring in a single application.
  • Creams or aqueous solutions of 5 to 7% hydrogen peroxide or urea peroxide are the primary developers commercially employed.
  • developers which have been suggested include chloroates, persulfates, perborates and sodium dichromate.
  • the lactams of this invention can also be added to the developer formultion for more uniform distribution and/or thickening effect as in cream applications.
  • the above dye components are often formulated into shampoos with oleate soaps or ethoxylated fatty alcohols to prevent drip and run-off.
  • the hair dye operations may be followed by a final conditioning treatment, a neutralizing rinse or an acid balanced shampoo containing in addition to cationic or amphoteric surfactants, cation-active emollients.
  • the present lactams may also be added to such neutralizing applications for conditioning effect.
  • lactam can be added to the above developing formulation instead of to the dye formulation or the amount of lactam can be divided between both the dye and developer formulations.
  • concentration of lactam in dye and developer system can range between about 0.75% and about 7.5% by weight, preferably between about 1% and about 5% by weight.
  • Bleaching involves a process for partial or complete oxidative degradation of the natural color pigment, i.e. melanin granules mainly present in cortex of hair fiber, or removal of applied dye pigment in or on the hair. As a side reaction, bleaching also attacks the hair cuticle proteins, i.e.
  • the most common bleaching agent comprises an aqueous soltuion of hydrogen peroxide of between about 5 to 9% strength in a formulation adjusted to a pH of from about 9 to about 11; although urea peroxide and other hydrogen peroxide creams incorporating a thickening agent such as a fatty alcohol or an alkanolamide can also be used.
  • the peroxide bleaching agent is employed with an activator which is added just before use, ammonium hydroxide being preferred by most practitioners since the ammonia swells the hair fiber to allow for peroxide penetration and is volatile which permits easy removal.
  • activators which have been employed include sodium carbonate and ethanolamines.
  • Bleach accelerators and boosters such as persulfate salts of ammonia, potassium and sodium may be used as well and conditioners e.g. ammonium oleate soap, a lipophilic surfactant, cholesterol and lanolin derivatives, are generally included in the peroxide formulation. Notwithstanding the generous use of such conditioning agents, noticeable drying, splitting and texture loss to the hair occurs.
  • the present lactams can be added to these formulations in the above amounts to minimize skin sensitivity, to preserve the tensile properties of the hair and to provide a strong conditioning action by forming a thin film over the hair cuticle which eliminates or minimizes hair dryness and breakage. Also, because of their high penetrating power and hair swelling properties, the present lactams are capable of diminishing the time hair is exposed to the chemical oxidation process.
  • Some typical hair bleaching formulations include the following.
  • Phosphoric Acid 10% C.P. to pH 3.5 to 4.0 100.00
  • lactams of this invention can be applied include hair blanching which employs sulfur dioxide or potassium permanganate followed by sodium thiosulfate to convert hair of mixed grey to snowy white and processes for certain hair dye removal techniques which employ a weak solution of sodium hydrosulfite, sodium thiosulfate or aminoiminomethane sulfinic acid.
  • Each of the representative compositions X and Y comprising the hair bleach formulation were divided into equal portions.
  • the first divided portions of X-Y were combined and immediately applied to portions of the hair selected for frosting on the left side of the scalp of the subject undergoing testing.
  • the subject had (color) hair of good texture and quality.
  • 1 wt. % of the quaternized dimethyl octadecyl-[N-(2-pyrrolidonyl)methyl] ammonium chloride was added to the remaining divided X-Y portions, after being combined.
  • the later mixture of combined X-Y portions, containing the quaternized lactam was applied to equal portions of the hair selected for frosting on the right side of the scalp of said subject .
  • the quaternized lactam, dimethyl octadecyl-[N-(2- pyrrolidonyl)methyl] ammonium chloride was also evaluated as an additive to a standard hair dye formulation namely (Loving Care - Medium Brown).
  • a standard hair dye formulation namely (Loving Care - Medium Brown).
  • Each of the representative compositions A, B and C comprising the hair dye formulation were divided in equal portions.
  • the first divided portions A-C were combined and immediately applied to the left side of the hair on the scalp of the subject undergoing testing. The subject had dark brown and grey hair of fine texture and quality.
  • 1 wt. % of the quaternized dimethyl octadecyl-[N-(2-pyrrolidonyl)methyl] ammonium chloride was added.
  • the later combined A-C portion, containing the quaternized lactam was applied to the hair on the right side of the scalp of said subject.
  • the lotions on the hair on each side of the scalp were allowed to remain for a period of 30 minutes, after which they were rinsed away with water.
  • the hair was then shampooed and blown dry.
  • the following evaluations comparing the hair on the right and left side of the scalp were made. The results of this evaluation are reported in Table III.
  • lactams of this invention can be added to a conventional shampoo tint to improve dye penetration and dye resistance to fading. As described, the lactam is added just prior to use.

Abstract

Une composition de changement permanent de la couleur des cheveux comprend une préparation aqueuse sur la base d'une oxydation et/ou dissolution de mélanine d'un intermédiaire d'un produit de coloration des cheveux, cette composition contenant en tant qu'agent de gonflement et de pénétration une amino lactame quaternisée ayant la formule (I) dans laquelle m est un nombre entier ayant une valeur comprise entre 1 et 4; R représente un alkylène ayant entre 3 et 8 atomes de carbone et éventuellement substitué avec un alkyle de C1 à C4; R1, R2 et R3 sont sélectionnés indépendamment parmi le groupe comprenant les radicaux alkyle, alkyle oxyde, alkylkydroxy, alkoxy, aryle, aralkyle, alkaryle, et alkylamidoalkyle, ces groupes ayant chacun entre 1 et 30 atomes de carbone, et au moins l'un de R1, R2 et R3 est un radical ayant entre 8 et 30 atomes de carbone; et X- est un anion de chlorure, de bromure ou iodure. L'invention concerne également l'utilisation de ces composés quaternisés.
EP19870907847 1986-10-24 1987-09-24 Composition used in permanent alteration of hair color Withdrawn EP0288553A4 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US06/922,923 US4732990A (en) 1986-10-24 1986-10-24 Quaternized nitrogen containing compounds
US922923 1986-10-24
US60284 1987-06-10
US07/060,284 US4834767A (en) 1987-06-10 1987-06-10 Compositions used in permanent alteration of hair color

Publications (2)

Publication Number Publication Date
EP0288553A1 EP0288553A1 (fr) 1988-11-02
EP0288553A4 true EP0288553A4 (en) 1991-08-07

Family

ID=26739776

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19870907847 Withdrawn EP0288553A4 (en) 1986-10-24 1987-09-24 Composition used in permanent alteration of hair color

Country Status (8)

Country Link
EP (1) EP0288553A4 (fr)
JP (1) JPH01501003A (fr)
AU (1) AU597454B2 (fr)
CA (1) CA1298787C (fr)
DK (1) DK350488A (fr)
IL (1) IL84085A (fr)
NO (1) NO882650L (fr)
WO (1) WO1988003017A1 (fr)

Families Citing this family (8)

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Publication number Priority date Publication date Assignee Title
US5157075A (en) * 1990-05-02 1992-10-20 Taenaka Mining Co., Ltd. Modified melanin
JP4007501B2 (ja) * 2001-03-30 2007-11-14 ザ プロクター アンド ギャンブル カンパニー 毛髪漂白製品
EP1300136A3 (fr) * 2001-10-04 2003-05-14 Henkel Kommanditgesellschaft auf Aktien Méthode pour changer la coloration des cheveux à base de sels de dithionite
US6709468B2 (en) * 2002-03-07 2004-03-23 Unilever Home & Personal Care Usa Gradual permanent coloring of hair using dye intermediates in alkaline water which contains quaternary ammonium compounds
FR2889660B1 (fr) * 2005-08-11 2007-10-19 Oreal Composition de coloration des fibres keratiniques comprenant au moins une base d'oxydation et un ester de sorbitan polyoxyethylene particulier
DE102005059647A1 (de) * 2005-12-12 2007-06-14 Henkel Kgaa Bleichmittel
CN102027072B (zh) * 2008-03-10 2014-10-29 佩拉化学有限公司 毛发着色组合物和方法
FR3015272B1 (fr) * 2013-12-19 2016-01-08 Oreal Procede de coloration mettant en œuvre des compositions riches en corps gras

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US2945863A (en) * 1958-06-24 1960-07-19 Gen Aniline & Film Corp Amides of aminoalkyl pyrrolidones
NL259654A (fr) * 1960-04-15
US3145147A (en) * 1961-02-20 1964-08-18 Gen Aniline & Film Corp Film forming composition of copolymers of nu-vinyl-epsilon-caprolactam
US3138610A (en) * 1961-03-10 1964-06-23 Gen Aniline & Film Corp Substituted imidazolines
FR1326561A (fr) * 1962-03-29 1963-05-10 Oreal Adjuvant pour fixateur de permanente
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LU81694A1 (fr) * 1979-09-17 1981-04-17 Oreal Composition contenant des derives d'ammonium bis quaternaires a deux chaines lipophiles destinee au traitement de matieres keratiniques et composes nouveaux utilises
FR2502949B1 (fr) * 1981-04-02 1985-10-18 Oreal Procede de preparation d'une composition de teinture ou de decoloration des cheveux, composition destinee a la mise en oeuvre de ce procede, et application de la composition obtenue par le procede
LU83911A1 (fr) * 1982-01-29 1983-09-02 Oreal Produit nettoyant des cheveux et de la peau a base d'acylise thionates et de polymeres cationiques
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FR2530141A1 (fr) * 1982-07-13 1984-01-20 Oreal Procede de mise en plis des cheveux et composition cosmetique pour sa mise en oeuvre
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Non-Patent Citations (1)

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Title
No further relevant documents have been disclosed. *

Also Published As

Publication number Publication date
IL84085A0 (en) 1988-03-31
NO882650D0 (no) 1988-06-15
AU8278587A (en) 1988-05-25
AU597454B2 (en) 1990-05-31
NO882650L (no) 1988-06-15
JPH01501003A (ja) 1989-04-06
DK350488D0 (da) 1988-06-24
WO1988003017A1 (fr) 1988-05-05
IL84085A (en) 1993-05-13
EP0288553A1 (fr) 1988-11-02
CA1298787C (fr) 1992-04-14
DK350488A (da) 1988-06-24

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