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US3253980A - Aminotriazine perhydrates oxidative hair compositions - Google Patents

Aminotriazine perhydrates oxidative hair compositions Download PDF

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Publication number
US3253980A
US3253980A US298450A US29845063A US3253980A US 3253980 A US3253980 A US 3253980A US 298450 A US298450 A US 298450A US 29845063 A US29845063 A US 29845063A US 3253980 A US3253980 A US 3253980A
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Prior art keywords
perhydrate
parts
hair
aminotriazine
perhydrates
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US298450A
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Klinge Gunther
Schnurch Roland
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Therachemie Chemische Therapeutische GmbH
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Therachemie Chemische Therapeutische GmbH
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Priority claimed from DEH37138A external-priority patent/DE1103934B/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/54—Three nitrogen atoms
    • C07D251/70—Other substituted melamines
    • 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
    • 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
    • A61K8/4966—Triazines or their condensed derivatives
    • 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
    • A61Q5/04—Preparations for permanent waving or straightening 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
    • C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines

Definitions

  • oxidizing agents for a variety of purposes, for instance for bleaching hair blond, for dyeing of hair with so called oxidizing dyes and as fixatives in the preparation of permanent w-aves, especially of cold waves.
  • the oxidizing component in such preparations predominantly is carbamide perhydrate (percarbamide) which offers a number of advantages over other oxidizers.
  • percarbamide carbamide perhydrate
  • canbamide perhydrate is easily incorporated and can be added to the hair dye or bleach immediately before application of the same.
  • the advantage of perca'rbamide resides in the latters better oxidizing effect which, with the perborate, either cannot be attained at all or, under certain conditions, can be attained only by application of comparatively large quantities.
  • the agents using percarbamide display the disadvantage that ;the latter decomposes after a short period of time during storage, especially at higher temperatures and at high humidity.
  • the hair treating agent has at best an impaired effect, or else loses its effect entirely.
  • novel agents for oxidizing treatment of human hair are characterized by a content of amino- 1.3.5-triazine perhydrate and exhibit not only a vastly improved effect, but also are of superior stability and can be stored for long periods of time.
  • Am-ino-l.3.5-triazine perhydrates applicable are especially those which contain at least two amino groups in the triazine component, as for instance, 2.4-diamino-6 phenyl- 1.3.5-triazine.
  • the particularly easily obtained perhydrate of melamine is employed.
  • a process for the production of these aminotriazine perhydrates has been described in assignees patent No. 3,055,- 897, issued September 25, 1962, entitled, Process for the Production of Triazine Perhydrate Compounds.
  • the H 0 content is approximately 21 percent by weight as a maximum, corresponding to equimolar amounts of melamine and H 0
  • products having a lesser H 0 content can be used in the agents according to the present invention, as obtained according to the manner of production of the aminotriazine perhydrate's.
  • mixtures of several aminotriazine perhydrates can be employed, if and when desired.
  • the oxidizing component of the air treating agents usually is added to these immediately before application.
  • solid powdered mixtures which contain the aminotriazine perhydrate together with the oxidation dyes, e.g., the sulfates or chlorohydrates of toluylene diamine, m-toluylene diamine, aminophenol, aminodiphenyl amine, and similar compounds.
  • the oxidation dyes e.g., the sulfates or chlorohydrates of toluylene diamine, m-toluylene diamine, aminophenol, aminodiphenyl amine, and similar compounds.
  • customary ingredients or" hair treating agents can be present in these mixtures, for instance thickeners, e.g., gum tr-agacanth, polyacrylic acid esters, polyvinyl pyrrolidone, methyl cellulose, canboxymethylcellulose or alginates; further, surface active substances may be present in these mixtures, such as alkyl sulfates, alkylaryl sulfates, or others. These mixtures are rendered ready for use by addition of a certain quantity of water or of alcohol diluted with water.
  • thickeners e.g., gum tr-agacanth
  • polyacrylic acid esters e.g., polyacrylic acid esters, polyvinyl pyrrolidone, methyl cellulose, canboxymethylcellulose or alginates
  • surface active substances may be present in these mixtures, such as alkyl sulfates, alkylaryl sulfates, or others.
  • the stability of the triazine perhydrates which, as mentioned above, is high, can even be improved by the addition of suitable stabilizers, such as magnesium silicate, mon-osodium phosphate, sodium pyrophosphate, phenacetin, or others.
  • suitable stabilizers such as magnesium silicate, mon-osodium phosphate, sodium pyrophosphate, phenacetin, or others.
  • the hair treating agents contain other customary ingredients, depending on the end use.
  • Such ingredients may be fatty alcohols, Wool fat, cholesterol, plant extracts, e.g., camomile, char-d and others, and also may contain perfumes.
  • Example 1 Melamine perhydrate, powdered for the purpose of incorporation in a hair dye, was stored at a temperature of 48 C. and at a relative humidity of 100 percent in paper bags with polyethylene liners. After 30 days storage under the above conditions, the melamine perhydrate was mixed into the hair dyeing cream, and the latter applied to the hair. The dyeing effect obtained therewith practically showed no difference from the effect obtained with a cream in which freshly made melamine perhydrate had been incorporated. Percarbamide, subjected to the same conditions, had practically lost its effect after four days.
  • Example 2 45 g. of a hair dyeing agent in cream form, containing fatty alcohol, fatty alcohol sulfates and water, and as dyes p-tolylene diarnine sulfate and diamino anisol sulfate, were mixed with 0.6 g. melamine perhydrate and applied to human hair at room temperature. After allowing the cream to act on the hair for 20-25 minutes, hair colorings were obtained which could 'be gotten only by applying a multiple thereof of sodium perborate, i.e., 5 grams.
  • the cream was prepared by melting 100 parts by weight mixed cetyl and stearyl alcohols at 70 C. and stirring into the melt at 80 C. 100 parts 30 percent ammonium lauryl sulfate. After this mixture had become homogeneous, 600 parts water at 80 C. were stirred in, followed by a mixture consisting of Pants Water 100 2.4-toluylene diamine sulfate 2.4-diamino anisol sulfate 0.3
  • the hair treating agent was prepared by melting at C. 100 parts mixed cetyl and stearyl alcohols with 20 pants lanolin, and stirring into this mix at C. parts 30% ammonium lauryl sulfate. After the viscous emulsion had become fully homogeneous, 700 parts water at 80 were added in portions, and the cream cooled to 40 C. with agitation. Then 30 parts ammonia (25%) were stirred in, and the emulsion made up to 1,000 parts with water. All parts listed are by weight.
  • Example 4 A powdery mixture consisting of G. 2.4-toluy1ene diarnine sulfate 1.0 2.4-diamino anisol sulfate L 0.03 Sodium pyrophosphate, anhydrous 3.0 Melamine perhydrate 8.0 Methyl cellulose 2.0
  • Example 5 Hair was treated with a cold wave agent, consisting of a 6 percent aqueous thioglycolic acid solution, adjusted to a pH of 9.6 with ammonia.
  • a cold wave agent consisting of a 6 percent aqueous thioglycolic acid solution, adjusted to a pH of 9.6 with ammonia.
  • an aqueous solution or suspension, respectively, containing 2 percent melamine perhydrate was applied. After allowing the latter (to act for approximately 10 minutes, an elastic and permanent wave was obtained.
  • a composition for the oxidative treatment of human hair consisting of 2.4-t0luy'lene diamine sulfate and 2.4- diamino anisol sulfate as oxidizing dyes, anhydrous sodium pyro'phosphate, methyl cellulose, in aqueous solution, and, as a stable oxidizer, 1 to 133 parts by weight, calculated on 100 parts of said dyes, sodium pyrophosphate and methyl cellulose, of a compound selected from the group consisting of melamine perhydrate and 2.3-diamino-6phenyl-1;3 .5 -triazine perhydrate.
  • a composition for the oxidative treatment of human hair containing a stable oxidizer and comprising oxidation dyes and thickeners, surface-active agents and plant extracts, said stableoxidizer consisting of 1 to 133 parts by weight, calculated on 100 parts of the other ingredients named exclusive of water, of a compound selected from the group consisting of melamine per-hydrate and 2.3-diam-ino-6- phenyl-1.3.5-triazine perhydrate.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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  • Veterinary Medicine (AREA)
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Description

United States Patent 2 Claims. (31. I167-88) The invention relates to agents for the oxidizing treatment of human hair, and, more panticularly, to such agents containing aminotriazine perhydrates. It is a continuation-in-pant of our application Serial Number 44,878, filed July 25 1960, and now abandoned.
Human hair is treated with oxidizing agents for a variety of purposes, for instance for bleaching hair blond, for dyeing of hair with so called oxidizing dyes and as fixatives in the preparation of permanent w-aves, especially of cold waves.
The oxidizing component in such preparations predominantly is carbamide perhydrate (percarbamide) which offers a number of advantages over other oxidizers. On account of its solid state, canbamide perhydrate is easily incorporated and can be added to the hair dye or bleach immediately before application of the same. As compared to sodium perborate, which also is employed, the advantage of perca'rbamide resides in the latters better oxidizing effect which, with the perborate, either cannot be attained at all or, under certain conditions, can be attained only by application of comparatively large quantities.
However, the agents using percarbamide display the disadvantage that ;the latter decomposes after a short period of time during storage, especially at higher temperatures and at high humidity. Thus, the hair treating agent has at best an impaired effect, or else loses its effect entirely.
It has now been found that these disadvantages can be overcome by the use of the agents according to this invention. The novel agents for oxidizing treatment of human hair are characterized by a content of amino- 1.3.5-triazine perhydrate and exhibit not only a vastly improved effect, but also are of superior stability and can be stored for long periods of time.
Am-ino-l.3.5-triazine perhydrates applicable are especially those which contain at least two amino groups in the triazine component, as for instance, 2.4-diamino-6 phenyl- 1.3.5-triazine. Preferably, however, the particularly easily obtained perhydrate of melamine is employed. A process for the production of these aminotriazine perhydrates has been described in assignees patent No. 3,055,- 897, issued September 25, 1962, entitled, Process for the Production of Triazine Perhydrate Compounds.
In the case of melamine perhydrate, the H 0 content is approximately 21 percent by weight as a maximum, corresponding to equimolar amounts of melamine and H 0 However, products having a lesser H 0 content can be used in the agents according to the present invention, as obtained according to the manner of production of the aminotriazine perhydrate's. Also, mixtures of several aminotriazine perhydrates can be employed, if and when desired. As stated above, the oxidizing component of the air treating agents usually is added to these immediately before application. With the high stability of the aminotriazine perhydrates, however, it is feasible, for instance in the case of dyeing agents, to use solid powdered mixtures which contain the aminotriazine perhydrate together with the oxidation dyes, e.g., the sulfates or chlorohydrates of toluylene diamine, m-toluylene diamine, aminophenol, aminodiphenyl amine, and similar compounds. Other customary ingredients or" hair treating agents can be present in these mixtures, for instance thickeners, e.g., gum tr-agacanth, polyacrylic acid esters, polyvinyl pyrrolidone, methyl cellulose, canboxymethylcellulose or alginates; further, surface active substances may be present in these mixtures, such as alkyl sulfates, alkylaryl sulfates, or others. These mixtures are rendered ready for use by addition of a certain quantity of water or of alcohol diluted with water. The stability of the triazine perhydrates which, as mentioned above, is high, can even be improved by the addition of suitable stabilizers, such as magnesium silicate, mon-osodium phosphate, sodium pyrophosphate, phenacetin, or others. When the components other than aminotriazine perhy- .drate are in aqueous solution or in emulsion and the perhydrate is added only immediately before application, the incorporation of stabilizers is superfluous.
Furthermore, the hair treating agents contain other customary ingredients, depending on the end use. Such ingredients may be fatty alcohols, Wool fat, cholesterol, plant extracts, e.g., camomile, char-d and others, and also may contain perfumes.
The outstanding stability of the aminotriazine perhydrates is evident from the example of melamine perhydrate (molar ratio of melamine to H 02 equaling 1:1), as shown in Table 1 below. In that table, column 1 gives the test number, column 2 shows the test temperature, column 3 the length of time of the tests, column 4 shows the loss of active oxygen in melamine per-hydrate, whereby in Tests 1-3 unstabilized melamine perhydrate had been used, whereas in Test 4 a preparation had been used to which 10 percent Na-H PO.,-H O had been added. Column 5 shows the loss of active oxygen in a stabilized percarbamide, as available on the market.
TABLE 1 Percent loss of active oxygen Test N0. Temp., Time,
0. hrs.
Melamine Percarbamide perhydrate The invention now will be further illustrated by the following examples. However, it should be understood that these are given merely by way of explanation, not of limitation, and that numerous changes may be made in the details without departing from the spirit and scope of the invention as hereinafter claimed.
Example 1 Melamine perhydrate, powdered for the purpose of incorporation in a hair dye, was stored at a temperature of 48 C. and at a relative humidity of 100 percent in paper bags with polyethylene liners. After 30 days storage under the above conditions, the melamine perhydrate was mixed into the hair dyeing cream, and the latter applied to the hair. The dyeing effect obtained therewith practically showed no difference from the effect obtained with a cream in which freshly made melamine perhydrate had been incorporated. Percarbamide, subjected to the same conditions, had practically lost its effect after four days.
Example 2 45 g. of a hair dyeing agent in cream form, containing fatty alcohol, fatty alcohol sulfates and water, and as dyes p-tolylene diarnine sulfate and diamino anisol sulfate, were mixed with 0.6 g. melamine perhydrate and applied to human hair at room temperature. After allowing the cream to act on the hair for 20-25 minutes, hair colorings were obtained which could 'be gotten only by applying a multiple thereof of sodium perborate, i.e., 5 grams.
The cream was prepared by melting 100 parts by weight mixed cetyl and stearyl alcohols at 70 C. and stirring into the melt at 80 C. 100 parts 30 percent ammonium lauryl sulfate. After this mixture had become homogeneous, 600 parts water at 80 C. were stirred in, followed by a mixture consisting of Pants Water 100 2.4-toluylene diamine sulfate 2.4-diamino anisol sulfate 0.3
Ammonia (25%) 5 Then, 5 parts sodium sulfite, dissolved in parts water were added. After cooling and continued homogenization 5 more pants ammonia were added, and the mixture brought to 1,000 parts by addition of water. All parts given are by weight.
Example 3 g. of an oil-in-water emulsion, alkal-ized with ammonia and containing fatty alcohols, alcohol sulfates, wool fat and water, were mixed with 12 g. melamine perhydrate and used for rendering human hair blond. After allowing this agent to act on the hair for 20-30 minutes, the hair thus treated was of a good blond color which corresponded 1110 that obtained by substituting percarbamide for melamine perhydrate under otherwise equal condition-s. Sodium perborate, even when used in an excess, lightened the air 't-hus treated but little.
The hair treating agent was prepared by melting at C. 100 parts mixed cetyl and stearyl alcohols with 20 pants lanolin, and stirring into this mix at C. parts 30% ammonium lauryl sulfate. After the viscous emulsion had become fully homogeneous, 700 parts water at 80 were added in portions, and the cream cooled to 40 C. with agitation. Then 30 parts ammonia (25%) were stirred in, and the emulsion made up to 1,000 parts with water. All parts listed are by weight.
4 Example 4 A powdery mixture consisting of G. 2.4-toluy1ene diarnine sulfate 1.0 2.4-diamino anisol sulfate L 0.03 Sodium pyrophosphate, anhydrous 3.0 Melamine perhydrate 8.0 Methyl cellulose 2.0
was mixed with 100 ml. water and well stirred several times. The slightly viscous liquid was applied to the hair for dyeing at body temperature in the customary manner. After an application time of 20 minutes, gray hair obtained a dark brown to black color. It is to be noted that substantially 133 parts melamine perhydrate are present, calculated on 100 parts of the total ingredients other than water.
Example 5 Hair was treated with a cold wave agent, consisting of a 6 percent aqueous thioglycolic acid solution, adjusted to a pH of 9.6 with ammonia. In order to fix the now wavy hair, an aqueous solution or suspension, respectively, containing 2 percent melamine perhydrate, was applied. After allowing the latter (to act for approximately 10 minutes, an elastic and permanent wave was obtained.
We claim as our invention:
1. A composition for the oxidative treatment of human hair consisting of 2.4-t0luy'lene diamine sulfate and 2.4- diamino anisol sulfate as oxidizing dyes, anhydrous sodium pyro'phosphate, methyl cellulose, in aqueous solution, and, as a stable oxidizer, 1 to 133 parts by weight, calculated on 100 parts of said dyes, sodium pyrophosphate and methyl cellulose, of a compound selected from the group consisting of melamine perhydrate and 2.3-diamino-6phenyl-1;3 .5 -triazine perhydrate.
2. A composition for the oxidative treatment of human hair containing a stable oxidizer and comprising oxidation dyes and thickeners, surface-active agents and plant extracts, said stableoxidizer consisting of 1 to 133 parts by weight, calculated on 100 parts of the other ingredients named exclusive of water, of a compound selected from the group consisting of melamine per-hydrate and 2.3-diam-ino-6- phenyl-1.3.5-triazine perhydrate.
References Cited by the Examiner FOREIGN PATENTS 1,141,749 12/1962 Germany.
JULIAN S. LEVI'IT, Primary Examiner.
VERA C. CLARKE, Assistant Examiner.

Claims (1)

1. A COMPOSITION FOR THE OXIDATIVE TREATMENT OF HUMAN HAIR CONSISTING OF 2.4-TOLUYLENE DIAMINE SULFATE AND 2.4DIAMINO ANISOL SULFATE AS OXIDIZING DYES, ANHYDROUS SODIUM PYROPHOSPHATE, METHYL CELLULOSE, IN AQUEOUS SOLUTION, AND, AS A STABLE OXIDIZER, 1 TO 133 PARTS BY WEIGHT, CALCULATED ON 100 PARTS OF SAID DYES, SODIUM PYROPHOSPHATE AND METHYL CELLULOSE, OF A COMPOUND SELECTED FROM THE GROUP CONSISTING OF MILAMINE PERHYDRATE AND 2.3-DIAMINO-6-PHENYL-1.3.5-TRIAZINE PERHYDRATE.
US298450A 1959-08-08 1963-07-29 Aminotriazine perhydrates oxidative hair compositions Expired - Lifetime US3253980A (en)

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Application Number Priority Date Filing Date Title
DET17066A DE1141749B (en) 1959-08-08 1959-08-08 Process and means for oxidative hair treatment
DEH37138A DE1103934B (en) 1959-08-08 1959-08-08 Process for the preparation of new organic perhydrate compounds

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US298450A Expired - Lifetime US3253980A (en) 1959-08-08 1963-07-29 Aminotriazine perhydrates oxidative hair compositions

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US3617167A (en) * 1965-08-05 1971-11-02 Therachemie Chem Therapeut Methods and compositions containing 4-aminopyrazolones for the dyeing of human hair
US3838965A (en) * 1970-07-13 1974-10-01 Oreal Dyeing keratinous fibers with azaindoanilines
US3853464A (en) * 1969-08-11 1974-12-10 Oreal Human hair dyeing compositions containing diphenylamines
US3986825A (en) * 1972-06-29 1976-10-19 The Gillette Company Hair coloring composition containing water-soluble amino and quaternary ammonium polymers
US4008999A (en) * 1974-02-22 1977-02-22 Societe Anonyme Dite: L'oreal N,N-dialkylamino diphenylamines for dyeing keratinic fibers
US20040141930A1 (en) * 2002-10-23 2004-07-22 Frederic Legrand Oil-in-water oxidizing cream emulsion for treating human keratin fibers

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CA724663A (en) * 1960-05-05 1965-12-28 H. Wilson James Detergent compositions
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US3400198A (en) * 1963-08-28 1968-09-03 Procter & Gamble Wave set retention shampoo containing polyethylenimine polymers
DE1212684B (en) * 1963-09-04 1966-03-17 Therachemie Chem Therapeut Preparations for coloring hair
DE1271885B (en) * 1964-01-04 1968-07-04 Henkel & Cie Gmbh Liquid, storage-stable detergents, bleaching agents and oxidizing agents
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US3373107A (en) * 1964-07-16 1968-03-12 Milchem Inc Friction pressure reducing agents for liquids
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US3320078A (en) * 1965-01-18 1967-05-16 Archer Daniels Midland Co Process for insolubilizing protein
CA783534A (en) * 1965-06-15 1968-04-23 Unilever Limited Liquid detergent compositions
US3457312A (en) * 1965-10-24 1969-07-22 Armour Ind Chem Co Amine oxides
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US3483178A (en) * 1968-04-18 1969-12-09 Monsanto Co Esters,salts,and acids of organo-phosphono-amine oxides
US3951878A (en) * 1969-03-05 1976-04-20 Millmaster Onyx Corporation Imidazoline oxides
US4058488A (en) * 1971-11-23 1977-11-15 Millmaster Onyx Corporation Imidazoline oxides
US3950510A (en) * 1972-08-01 1976-04-13 Lever Brothers Company Conditioning shampoo containing a water-insoluble hair cosmetic agent
US4007261A (en) * 1972-08-23 1977-02-08 Millmaster Onyx Corporation Pearlescent hair conditioner
US4048338A (en) * 1973-11-09 1977-09-13 Colgate-Palmolive Company Aqueous cosmetic composition containing amine oxides
CA1258636A (en) * 1984-07-20 1989-08-22 Terry Gerstein Low ph hair conditioner compositions containing amine oxides
US4714610A (en) * 1984-07-20 1987-12-22 Revlon, Inc. Low pH hair conditioner compositions containing amine oxides
US4970340A (en) * 1985-07-01 1990-11-13 Ethyl Corporation Amine oxide process and composition
US4659565A (en) * 1985-07-01 1987-04-21 Ethyl Corporation Amine oxide hair conditioner
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CA2145980C (en) * 1994-03-31 2003-01-07 Shunsuke Takeda Hair revitalizing composition
US5844029A (en) * 1995-09-25 1998-12-01 General Electric Company Polymer compositions containing hydrocarbon amine oxide and hydrocarbon amine oxide stabilizer compositions
US5866718A (en) * 1997-03-20 1999-02-02 General Electric Company Synthesis of tertiary amine oxides

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3617167A (en) * 1965-08-05 1971-11-02 Therachemie Chem Therapeut Methods and compositions containing 4-aminopyrazolones for the dyeing of human hair
US3853464A (en) * 1969-08-11 1974-12-10 Oreal Human hair dyeing compositions containing diphenylamines
US3838965A (en) * 1970-07-13 1974-10-01 Oreal Dyeing keratinous fibers with azaindoanilines
US3986825A (en) * 1972-06-29 1976-10-19 The Gillette Company Hair coloring composition containing water-soluble amino and quaternary ammonium polymers
US4008999A (en) * 1974-02-22 1977-02-22 Societe Anonyme Dite: L'oreal N,N-dialkylamino diphenylamines for dyeing keratinic fibers
US20040141930A1 (en) * 2002-10-23 2004-07-22 Frederic Legrand Oil-in-water oxidizing cream emulsion for treating human keratin fibers

Also Published As

Publication number Publication date
CH440554A (en) 1967-07-31
LU38942A1 (en) 1961-01-12
NL254590A (en)
NL122204C (en)
US3098794A (en) 1963-07-23
DE1141749B (en) 1962-12-27
CH379515A (en) 1964-07-15

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