Classifications

• • 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
• • 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
  • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
• • 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
  • A61K8/415—Aminophenols
• • 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
  • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
  • A61K8/445—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof aromatic, i.e. the carboxylic acid directly linked to the aromatic ring
• • 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
  • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
  • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
• • 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
• • 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
  • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
• • 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

Definitions

• the invention relates to dyeing hair with a 1-amino-4- substituted alkyl amino benzene and a coupler selected from the group consisting of substituted phenols, R5COCHZCOR5, and
• R is methyl; R is selected from the group consisting of methyl and ethoxy; R is phenyl; R is selected from the group consisting of p-carboxyphenylarnino and m-carboxyphenylamino; and Y is selected from the group consisting of phenyl, p-sulfophenyl, m-sulfophenyl and 2- chloro-S- sulfophenyl.
• This invention relates to a method of dyeing hair using paradiaminobenzene derivatives and couplers, and to compositions for use in that method.
• the present invention relates to a new method of dyeing hair which has not the aforesaid disadvantages because the dyes formed have exceptional fastness to light, at least in regard to the times, of the order of one year, which are relevant to hair dyeing.
• the amine employed does not in itself possess any satisfactory coloring power, so that the shade obtained results from the interaction of the coupler with the amine.
• the method of the present invention comprises applying to the hair:
• R represents a hydrogen atom, or a methyl, ethyl or propyl radical and X is selected from the group consisting of 3,506,389 Patented Apr. 14, 1970 in which R is selected from the group consisting of methyl, ethyl and propyl, and R is selected from the group consisting of CH CONH -CH COOH,
• R is selected from the group consisting of CH --NHCOCH -NHCH CONH and -NHCOCH N(C H and R is selected from the group consisting of hydrogen and methyl;
• R is methyl and R is selected from the group consisting of methyl and ethoxy;
• R is phenyl and R is selected from the group consisting of p-carboxyphenylamino and m-carboxyphenylamino; 7
• Y is selected from the group consisting of phenyl, p-sulfonphenyl, m-sulfophenyl and 2-chloror5-sulfophenyl;
• the amine and coupler can be used, where appropriate, in the form of their salts.
• the method can conveniently be carried out by applying the said amine and the said coupler in the form of aqueous solution in consecutive order to the hair, and the oxidizing agent can be conveniently in either the solution of amine or coupler.
• the solutions can contain other dyestuffs which may be employed under the same conditions as direct dyes, for example azo dyes. They can also contain wetting agents, dispersing agents, penetration agents and other ingredients generally employed in hair dyeing.
• the couplers of Formula II provide shades of blue
• the couplers of Formula HI provide shades of yellow
• the couplers of Formula 1V provide shades of red.
• the dyes obtained using the method of this invention have proved to have exceptional resistance to light as compared with dyes hitherto used for hair dyeing. Moreover, a study of the toxicity of the dyes provided by the present invention has shown, contrary to what might have been expected, that they are probably less toxic, and in any case, not more toxic, than the dyes based upon p-phenylenediamine which are at present in use for hair dyeing, which themselves produce appreciable allergy reactions only in extremely rare cases.
• the amines of Formula I have the advantage that they do not impart any color to the hair when applied in the absence of couplers.
• the colors obtained using the present invention result essentially from the combination of the amine and of the coupler and not from the superimposition of two dis-' tinct colors, as is the case in the majority of dyeing solutions hitherto employed.
• This property is most valuable in practice, because it has been observed that the shades obtained in the earlier processes vary from one person to another and even from one place to another on the same hair by reason of a selectivity in the taking of the amines and the couplers on the hair, which disadvantage is avoided with the invention since the color obtained results only from the amine-coupler association.
• the solution which can be kept without deteriorating, is mixed at the time of use with an equal volume of hydrogen peroxide vol.), and when applied to white hair dyes it blue.
• the method of dyeing in this and in the folowing examples consisted of applying the dyeing solution to the hair at ambient temperature, leaving the hair for 20 minutes and then successively rinsing, shampooing, rinsing again and drying.
• EXAMPLE 2 There is prepared a solution having the following composition: 4-amino-3-methyl-N-ethyl-N-carbamyl methylaniline sulphate-1.28 g. 3-N-acetamino-6-methyl-phenol1.65 g. Ammonia solution (22 B.)-6 cc. Water q.s. for 50 cc.
• This solution has a pH of 10.6.
• This solution D has a pH of 10.6
• This solution which has a pH of 10, can be kept well without decomposition. It is mixed with an equal volume of hydrogen peroxide (20' vol.) and appled immediately to white hair, giving a deep orange-yellow color.
• This solution which has a pH of 10.7, can be kept well without decomposition.
• An equal volume of hydrogen peroxide (20 vol.) is added to the solution, and the mixture is applied immediately to white hair giving a dark purplish-red color.
• This solution which has a pH of 10.5, can be kept well without decomposition.
• an equal volume of hydrogen peroxide (20 vol.) By adding thereto an equal volume of hydrogen peroxide (20 vol.) and applying it to white hair, a pale reddish-purple color is obtained.
• EXAMPLE 9 There are prepared three solutions E, F and G, each containing: 4-amino-3-methyl-N-ethyl-N-[fl-(methylsulphamido) ethyl] aniline sulphate2.9 g.
• G+E All shades ranging from purple-red to dark greenish-blue.
• solution L is 10.6.
• Solution L is then applied for 20 minutes at ambient temperature to the hair previously treated with solution K, and after 20 minutes the hair is rinsed.
• Solution N is applied to the grey hair previously treated by solution K, as described in Example 11, and the same color is obtained as in Example 11.
• EXAMPLE 14 White hair is treated by a solution containing:
• the coloring obtained is grey-greenish.
• EXAMPLE 16 A solution is prepared as follows: 4-amino, [N-ethyl,N- (N'-diethyl) -carbamylmethyl] aniline chlorhydrate-1.45 g. 6-methyl, 3-(N-carbamylmethyDarnino, phenol-222 g.
• EXAMPLE 17 A solution is prepared as follows: in which R2 represents methoxy, 4-amino, 3-methyl[N-ethyl, N-(N'-diethyl)-carbamyl- 1O (2) methyl] aniline chlorhydratel.50 g. 011 B-acetamino, phenol3 g. Aqueous solution of ammonia at 22 B.-6 cc. RF Water q.s.p. 50 cc. 15 The pH of said solution is 10.6 R
• NHCH CON C H EXAMPLE 1 ; 2 2 h and NHCOCH N(C H and R is selected A Solutlon prepared as follows from the group consisting of hydrogen and methyl; 4 (Emailing),ilglzthyhN-carbamylmethyl)an1l1ne chlorhy- (3) 3-[(N-diethyl)carbamylmethyl1-amino, phenol2.22 g. in which R5 methyl and 6 is Selected from the Aqueous solution of ammonia at 22 B.6 cc. group cohslshhg of methyl and ethoxy; Water q.s.p. 100 cc.
• R COCH COR The p of Said Solution is in which R, is phenyl and R is selected from the When said solution is applied in the same conditions group consisting of P-Cafhoxyphehylammo and as mentioned for Example 2 with hydrogen peroxide, a yp y and crimson-grey hue is obtained. (5)
• EXAMPLE 19 f ff A solution is prepared as follows: 0:0 N 4 amino,(N-ethyl,N-carbamylmethyl)-aniline chlorhydrate-l.l5 g. Y 6 methyl,3 y y y l amino, in which Y is selected from the group consisting of phenol2.36 g. 40 Phenyl, p-sulfophenyl, m-sulfophenyl and 2-chloro- Aqueous solution of ammonia at 22 B'.6 cc. 5-sulfophenyl; and Water q.s.p. 100 cc. (c) an oxidizing agent; The pH of said solution is 10.6.
• the method of the 2. is not limited to the application to the i agcnt i h d id hair of a solution containing together the amine, the cou- 3 Th thod as l i d i l i 2, i hi h the aid pler or couplers and hydrogen peroxide, but includes the 50 hydrogen peroxide is applied to the hair in an aqueous successive application of different solutions each containl ti f th id i ing one or more of the iugerdicnts. 4.
• a composition of matter for dyeing hair which coman amine of the formula prises an aqueous solution having a pH of 9 to 11 and NH2 hair coloring amounts of (a) a colorless amine having the formula R1 NHz .R I X in which R is selected from the group consisting of hydrogen, methyl, ethyl and propyl, and X is selected f th 0 t f (1) mm 6 gr up consls i 1n whlch R 18 selected from the group consisting of hydrogen, methyl, ethyl and propyl, and X is selected from the group consisting of 1 R in which R is selected from the group consisting of methyl, ethyl and propyl, and R is selected from the group consisting of CH CONH CH COOH, OH CH NHSO CH -CH CON(C H (2) N- in which R is selected from the group consisting of piperidyl; and (3) N-morpholyl; methyl, ethyl and propyl, and R is
• R is selected from the group consisting of CH NHCOCH NHCH CONH group consisting of p-carboxyphenylamino and mcarboxyphenylamino;
• composition as claimed in claim 5 further comprising an oxidizing agent.
• composition for dyeing hair of claim 5, wherein said amine is selected from the group consisting of 4- amino 3 methyl-N-ethyl-N-(,B-methyl-sulfamidoethyl)- aniline sulfate, 4 amino-3-methyl-N-ethyl-N-carbamylmethyl-aniline sulfate; 4-amino-N-ethyl-N-carbamylmethylaniline; 4-amino-N-ethyl N carbamylmethylaniline chlorhydrate; N-(4-aminophenyl)-morpholine sulfate; N- (4-aminophenyl) pipe ridine sulfate; N-methyl-N-(4'- aminophenyl)- 3-aminoacetic acid; 4-amino-[N-ethyl-N- (N'-diethyl)-carbamylrnethyl]aniline chlorhydrate; and 4- amino-3-methyl-[N-ethy
• composition for dyeing hair of claim 5, wherein said coupler is selected from the group consisting of 6- methyl 3 [(N'-diethyl)carbamylmethyl]aminophenol; 2,5-dimethylphenol; N-acetamino-3-methyl-6-phenol; 4- methoxyphenol; 3-acetaminophenol; 3-N- (carbamyl-methylamino)phenol; 1-phenyl-3-methyl-5-pyrazo1one; 4-benzoylacet-aminobenzoic acid; 3-methyl-(l-p-sulfophenylpyrazol-5-one) sulfonic acid; 3-[a-(N'-diethyl)amino] acct aminophenol; 6-methyl-3-[a-(N-diethyl)-amino] acetaminophenol; 6 methyl 3 (N-carbamylmethyl)- aminophenol; and 3-[ (N'-diethyl) carbamylmethyl] amino phenol.
• composition of claim 5 wherein said pH is between 10 and 10.7.

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• Life Sciences & Earth Sciences (AREA)
• Health & Medical Sciences (AREA)
• Animal Behavior & Ethology (AREA)
• General Health & Medical Sciences (AREA)
• Public Health (AREA)
• Veterinary Medicine (AREA)
• Birds (AREA)
• Epidemiology (AREA)
• Cosmetics (AREA)
• Coloring (AREA)

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Cited By (7)

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Citations (9)

• 1963
  • 1963-08-01 FR FR943485A patent/FR1403633A/fr not_active Expired
• 1964
  • 1964-07-20 US US383937A patent/US3506389A/en not_active Expired - Lifetime
  • 1964-07-22 BE BE650836D patent/BE650836A/xx unknown
  • 1964-07-22 CH CH960764A patent/CH438585A/fr unknown
  • 1964-07-24 DE DE1794383*CA patent/DE1794383C3/de not_active Expired
  • 1964-07-28 AT AT648864A patent/AT264017B/de active
  • 1964-07-29 NL NL6408654A patent/NL6408654A/xx unknown
  • 1964-07-29 IT IT16730/64A patent/IT965508B/it active
  • 1964-08-04 GB GB31109/64A patent/GB1025916A/en not_active Expired

Patent Citations (9)

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