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
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/41—Amines
  • A61K8/413—Indoanilines; Indophenol; Indoamines
• • 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
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/35—Ketones, e.g. benzophenone
  • A61K8/355—Quinones
• • 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

• a composition for dyeing keratinous fibers comprises an aqueous solution of at least one quinoneimine and an aqueous solution of at least one coupler.
• This invention relates to a process and composition for dyeing keratinous fibers, particularly human hair. More specifically, this invention relates to dyeing human hair with a dyeing composition containing a quinone imine and a coupler.
• keratinous fibers and, in particular, human hair have been dyed by employing oxidation dyes.
• compounds commonly referred to as bases have been employed. These bases are, properly speaking, not dyes, but under certain conditions they are capable of dyeing the hair as the result of an oxidation process.
• bases are essentially aromatic orthoor paradiamines, orthoor paraaminophenols, or their derivatives.
• oxidation of these compounds usually takes place at the moment of their application to the fibers to be dyed by the addition thereto of an oxidizing agent such as hydrogen peroxide.
• couplers are aromatic metadiamines, metaaminophenols, or metadiphenols, or their derivatives.
• Such a process consists in adding at the moment of use an oxidizing agent such as hydrogen peroxide to a mixture of the base and the coupler.
• an oxidizing agent such as hydrogen peroxide
• the molar ratio of couplerto quinoneimine employed is generally greater than or equal to 1.
• Couplers used in the process according to this invention can be any of those couplers known in the prior art. Thus, it is possible to use an aromatic metadiamine, a metaaminophenol, a metadiphenol, or their derivatives, as well as an arylpyrazolone or a pyridine derivative.
• Representative couplers useful in the practice of the present invention include resorcinol,
• the quinoneimines used in the process according to this invention are quinone monoor diimines derived from conventional oxidation bases, i.e., compounds whose molecule comprises an aromatic or heterocyclic nucleus alternatively substituted by (1) two amino groups or (2) an amino group and a hydroxyl group which are.
• oxidation bases can be aromatic orthoor paradiamlnes or orthoor paraaminophenols or their derivatives, both functional and with substitution, such as those described, for example, in US. Pat. 3,506,389 and incorporated herein by reference.
• the oxidation base can have the formula NHz wherein R is selected from the group consisting of hydrogen and lower alkyl having 1-3 carbon, atoms and X is selected from the group consisting of (1) wherein R is lower alkyl having 1-3 carbon atoms and R is selected from the group consisting of -CH CONH CH COOH, --CH CH NHSO CH and and the other entitled, Process for Preparing Indophenols and Their Use in Dyes for Coloring Keratin Fibers, S.N. 49,905, filed June 25, 1970, now abandoned, both being incorporated herein by reference.
• a typical example of the procedure involved in oxidizing the base to a quinoneimine comprises heating the base at a temperature ranging between 30 and C. in an anhydrous solvent such as ethyl ether or isopropyl ether and in the presence of an oxidizing agent such as those listed above.
• the oxidizing agent is present in amounts ranging between 1 to 2 times the stoichiometric quantity for oxidizing the base, and preferably. 1.5 times this stoichiometric quantity.
• the resulting quinoneimine obtained in said reaction can be isolated from the reaction mass by any convenient separation technique, such as by filtration. Thereafter,
• the filtrate containing the quinoneimine can be evaporated ciently stable are used in isolated form.
• these quinoneimines are in the'form of a powder which is put into an aqueous solution at the time of use. These quinoneimines are applied to the fibers to be dyed in the said solution which has generally a neutral pH. With such a solution no extraneous oxidizing agent is required.
• an aqueous solution of at least one coupler is applied in a first stage operation to the fibers to be dyed. This coupler-containing solution is left in contact with the hair for to 20 minutes. Thereafter, there is applied, in a second stage operation, preferably after rinsing the fibers, an aqueous solution of at least one quinoneimine, which is left in contact with the fibers for about 5 to 30 minutes.
• a solution of at least one coupler is mixed with a solution of at least one quinoneimine just before application to the hair, and the fibers to be dyed are impregnated with this mixture which is left in contact with the hair for 5 to 30 minutes.
• a principal advantage of this first embodiment of the process of this invention resides in the fact that it is possible to perform the dyeing operation at a neutral pH and in the absence of an extraneous oxidizing agent such as hydrogen peroxide.
• Such a process is highly desirable, especially in the case of porous hairs which poorly support an alkaline treatment and the action of hydrogen peroxide, or in the situation when it is desirable to avoid a possible allergy reaction to hydrogen peroxide on the part of the person whose hair is being dyed.
• an oxidizing agent such as hydrogen peroxide can be incorporated into the aqueous solution of the coupler or quinoneimine or their mixtures.
• An alkaline agent such as ammonia can also be added, if desired, to the solution containing the coupler to improve, for instance, the solubility of the coupler in said solution.
• the quinoneimine can be formed at the time of its application to the hair, by oxidizing an aqueous solution of a corresponding oxidation base with an oxidizing agent which effects the oxidation rapidly.
• the oxidizing agent which is employed in a molar excess relative to the base, can be, for example, potassium persulfate or ferricyanide.
• the oxidation is performed in accordance with conventional techniques such as in an alkaline medium having a pH ranging generally from about to '12, at ambient temperature and pressure.
• the aqueous solution can be made alkaline preferably by adding thereto suflicient amounts of ammonia to achieve the desired pH.
• the coupler containing aqueous solution is applied, in a first stage, to the fibers to be dyed and left in contact therewith for about 5 to 20 minutes.
• the fibers are then rinsed and, thereafter, in a second stage, the quinoneimine containing aqueous solution, which is prepared just immediately before its application to the hair, is applied to the hair.
• the quinoneimine containing solution is permitted to remain in contact with the hair for a period of about 5-30 minutes, after which the hair is rinsed and, if desired, shampooed. In this fashion, the desired color is imparted to the hair.
• the ratio between the molar concentration of quinoneimine and that of the coupler can vary within rather Wide limits, although preferably a molar excess of coupler is employed.
• the pH of the two solutions forming the composition of this invention can be neutral or alkaline and is, prefstably, tween. ab ut 7-10.
• composition according to this invention can obviously contain such conventional additives as wetting agents, dispersing agents, swelling agents, penetrating agents or other ingredients usually employed in hair dyeing compositions.
• dyes conventionally employed to color keratinous fibers for example, azo or anthraquinone dyes, can also be used.
• the dye composition of this invention can be in the form of aqueous solutions or in the form of a cream or gel.
• gray hair is impregnated with this solution in a first stage operation. After a wait of about 20 minutes, the hair is rinsed and impregnated with the following solution, prepared just before its application to the hair:
• This quinoneimine containing solution is allowed to contact for 20 minutes. Thereafter the hair is rinsed, shampooed and dried. A dark green dyeing is obtained.
• This quinoneimine solution is left in contact with the hair for 10 minutes after which the hair is rinsed, shampooed and dried. A deep blue dyeing is obtained.
• a second solution, designated as B, is prepared just before use:
• Gray hair is impregnated with this solution which is left in contact therewith for 10 minutes. The hair is then rinsed and the following solution, prepared at the moment of use, is applied:
• the above solution is allowed to act for 20 minutes. The hair is then rinsed, shampooed and dried. A night blue dyeing is obtained.
• the above solution is permitted to remain in contact with the hair for about 20 minutes. Thereafter the hair is rinsed, shampooed and dried. A blue green dyeing is obtained.
• This solution is applied to White hair for 15 minutes at ambient temperature. The hair is then rinsed in lukewarm water.
• Solution D is permitted to remain in contact with the hair for about 15 minutes after which the hair is rinsed, shampooed and dried. A strong night blue is obtained.
• Resorcinol g. (0.01 m.) 1.10 Na2HPO4 g Water, q.s.p cm. 100
• This solution is applied to gray hair for 15 minutes at ambient temperature. Thereafter the hair is rinsed in lukewarm water.
• Solution H is allowed to remain on the hair for 15 minutes after which the hair is rinsed, shampooed and dried. A brown coloration with blue glints is imparted to the hair.
• This solution is applied to bleached hair for minutes at ambient temperature.
• the hair is rinsed in lukewarm water.
• solution D prepared as set forth in Example 10 is applied to the hair and after it has been allowed to remain in contact with the hair for 15 minutes, the hair is rinsed, shampoosed and dried. An ash brown is obtained.
• EXAMPLE 14 A solution K made in the manner disclosed in Example 13 is applied to white hair for 10 to 15 minutes at ambient temperature. Thereafter the hair is rinsed in lukewarm water.
• solution L is prepared by admixing, just before use, solution I, disclosed in Example 12 and solution M, having respectively the following compositions:
• This solution is applied to bleached hair for 10 minutes at ambient temperature.
• the hair is then rinsed in lukewarm water.
• Solution E is allowed to remain in contact with the hair for 20 minutes, after which the hair is rinsed, shampoo d and dried. A gree b end is obtained.
• Gray hair is impregnated with this solution which is allowed to remain in contact therewith for 15 minutes. The hair is then rinsed and the following solution, prepared at the moment of use, is applied to the hair:
• a composition for dyeing 'keratinous fibers comprising an aqueous solution of a quinone-imine selected from the group consisting of Z-methoxy-5-methyl-benzoquinonediimine, 2,6 dimethyl S-methoxy-benzoquinonediimine, duroquinonediimine and 2,6-dimethyl-benzoquinoneimine, and a coupler selected from the group consisting of an aromatic metadiamine, a metaaminophenol, a metadiphenol, an arylpyrazolone and a pyridine derivative, said quinoneimine and coupler being present in amounts effective to dye said fibers and the ratio of the molar concentration of said coupler being less than or equal to one, the pH of said composition ranging between 7-10.
• a quinone-imine selected from the group consisting of Z-methoxy-5-methyl-benzoquinonediimine, 2,6 dimethyl S-methoxy-benzoquinonedii
• composition of claim 1 which also contains an oxidizing agent.
• composition of claim 2 wherein the oxidizing agent is selected from the group consisting of hydrogen peroxide, potassium persulrfate and potassium ferricyanide.
• composition of claim 1 wherein the pH is essentially neutral. 7
• composition of claim 1 wherein the pH is alkaline.
• a composition for dyeing keratinous fibers comprising an aqueous solution of a quinone-irnine selected from the group consisting of 2-methoxy-5-methyl benzoquinonediimine, 2,6 dimethyl-5-methoxy-benzoquinone-di imine, duroquinonediimine and 2,6-dimethyl-benzoquinoneimine, and a coupler selected from the group consisting of resorcinol, 2,6-diaminopyridine, 6-rnethyl-3-(N- carbarnylrnethylamino) phenol, 2 carbamylmethylamino- 4-hydroxy-toluene, 1 phenyl 3 methyl 5 pyrazolone, 2,5 dimethyl-phenol, Z-methyl S-acetamino-phenol, 7- hydroxy-phenomorpholine, 2,4-diaminoanisole and 2,6-dimethyl-B-amino-phenol, said quinoneimine
• a process for dyeing keratinous fibers comprising aplying to said fibers in a first stage an aqueous solution of a coupler selected from the group consisting of an aromatic metadiamine, a metaminophnol, a metadiphenol, an arylpyrazolone and a pyridine derivative, permitting said aqueous solution of said coupler to remain in contact with said fibers for a period of about 5-20 minutes and,
• aqueous solution of a quinoneimine selected from the group consisting of 2-methoxy-5-methylbenzoqninonediimine, 2, 6 dimethyl 5 methoxy benzoquinonediimine, duroquinonediimine and 2,6-dimethyl-benzoquinoneimine, permitting said aqueous solution of said quinoneimine to remain in contact with said fibers for a period of about 5- 30 minutes and rinsing and drying said fibers, the aqueous solutions of said coupler and said quinoneimine being applied in amounts effective to dye said fibers, each of said solutions having a pH of 7-10 with the molar concentration of said quinoneirnine to the molar concentration of said coupler being less than or equal to l.
• a quinoneimine selected from the group consisting of 2-methoxy-5-methylbenzoqninonediimine, 2, 6 dimethyl 5 methoxy benzoquinonediimine, duroquinone
• a process for dyeing keratinous fibers comprising applying to said fibers an effective amount of an aqueous solution of a mixture of a quinoneimine selected from the group consisting of Z-methoxy-S-methyl-benzoquinonediimine, 2,6 dimethyl-5-methoxy-benzoquinonediimine,
• a coupler selected from the group consisting of an aromatic metadiamine, a metaaminophenol, a metadiphenol, an arylpyrazolone and a pyridine derivative, to dye said fibers, permitting said aqueous solution to remain in contact with said fibers for a period of about 5-30 minutes, and rinsing and drying said fibers, said aqueous solution having a pH ott 7-10 and the ratio of the molar concentration of said quinoneimine to the molar concentration of said coupler being less than or equal to 1.

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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)
• Emergency Medicine (AREA)
• Cosmetics (AREA)
• Coloring (AREA)

Applications Claiming Priority (1)

Publications (1)

Family

ID=19726096

Family Applications (1)

Country Status (10)

Cited By (8)

Families Citing this family (1)

Family Cites Families (1)

• 1969
  • 1969-07-08 LU LU59063D patent/LU59063A1/xx unknown
• 1970
  • 1970-06-30 GB GB3175570A patent/GB1306613A/en not_active Expired
  • 1970-07-06 US US00052741A patent/US3730677A/en not_active Expired - Lifetime
  • 1970-07-07 IT IT69344/70A patent/IT979648B/it active
  • 1970-07-07 CH CH1026770A patent/CH538865A/fr not_active IP Right Cessation
  • 1970-07-07 AU AU17256/70A patent/AU1725670A/en not_active Expired
  • 1970-07-07 ES ES381549A patent/ES381549A1/es not_active Expired
  • 1970-07-07 BE BE753103D patent/BE753103A/xx unknown
  • 1970-07-07 NL NL7010002A patent/NL7010002A/xx unknown
  • 1970-07-07 FR FR707025072A patent/FR2051596B1/fr not_active Expired

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