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US3202579A - Phosphinic acid derivatives for protection of hair from damage in bleaching and dyeing the same - Google Patents

Phosphinic acid derivatives for protection of hair from damage in bleaching and dyeing the same Download PDF

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Publication number
US3202579A
US3202579A US310165A US31016563A US3202579A US 3202579 A US3202579 A US 3202579A US 310165 A US310165 A US 310165A US 31016563 A US31016563 A US 31016563A US 3202579 A US3202579 A US 3202579A
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hair
bleaching
damage
dyeing
acid derivatives
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US310165A
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Berth Peter
Reese Gunter
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Therachemie Chemische Therapeutische GmbH
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Therachemie Chemische Therapeutische GmbH
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
    • C07F9/3839—Polyphosphonic acids
    • 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
    • A61K8/55—Phosphorus compounds
    • 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
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/10—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen
    • D06L4/12—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen combined with specific additives
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S424/00—Drug, bio-affecting and body treating compositions
    • Y10S424/03—Hair bleach

Definitions

  • the invention relates to agents which prevent or, at least minimize, damage to hair, particularly human hair, when subjected to bleaching and dyeing operations.
  • oxidizing substances For the purpose of dyeing and bleaching of hair, oxidizing substances have long been used, such as hydrogen peroxide, percarbamide, perborate, persulfate and other compounds emitting active oxygen. It is a well known fact that that oxidizing treatment, aside from destroying pigments in the hair, also attacks the fibrous substance of the hair itself. The damage thus inflicted manifests itself, e.g., in an increased alkali solubility and in a decrease of the mechanical properties of the hair, e.g., a strong decrease in its tear resistance, diminishing gloss and grip and increasing brittleness.
  • X represents either OH or -NH
  • R is an aryl radical or an aliphatic radical having 1 to 5 carbon atoms, or the radical R2 (la) and wherein R and R respectively, denote individually, in Formula 1 as well as in Formula 1a, a hydrogen atom or an alkyl radical having 1 to 5 carbon atoms.
  • R and R respectively, denote individually, in Formula 1 as well as in Formula 1a, a hydrogen atom or an alkyl radical having 1 to 5 carbon atoms.
  • Compounds of the composition (2) which is one embodiment of Formula 1 above,
  • phosphorous acid can be reacted with carboxylic acid chlorides or carboxylic acid anhydrides or with mixtures of both such compounds to yield these compounds.
  • carboxylic acid chlorides or carboxylic acid anhydrides Readily available in large scale production are reaction products of phosphorous acid with acetyl chloride and/ or acetic anhydride.
  • carboxylic acid chlorides and phosphorous acid phosphorous trichloride and carboxylic acids can be used in suitable stoichiometrical proportions. Depending on the method of production, pure single products or mixtures of pure products are obtained.
  • the materials named can be employed on carrier substances or can be admixed to a solution, a gel, a cream or a powder, or else they may be used in combination with the oxidizing agent. Furthermore, they can be incorporated in a treating agent, such as a rinse or a hair wash.
  • the damage-preventing substances are applied in quantities of 0.01 to 10 percent by weight, calculated on the agent in which incorporated, and preferably in amounts of 0.1 to 2 percent by weight. If desired, larger amounts can be used, although this does not have any practical advantages.
  • the hair treating agents containing the damage-preventing substances also may contain, if desired, further customary additives, such as perfume oils, dyestuffs, thickeners, fatty alcohols, anionactive and cationactive and nonionic wetting agents.
  • Particularly suitable thickeners are cellulose derivatives, polyvinylpyrrolidone, polyacrylates, alginates and, in certain instances, fatty alcohols.
  • Suitable Wetting agents include fatty alcohol sulfates, alkyl sulfates and condensation products of fatty alcohols with ethylene oxide, whereby the alkyl radical in all instances has a chain length of 12 to 18 carbon atoms.
  • alkylbenzenesulfates and alkylpyridinium salts are also usable.
  • Hair treated with the agents according to the invention are distinguished by high gloss, improved hand or grip and especially good elasticity, as compared to hair which had been treated in the usual manner under equal conditions.
  • the difference in damage to the hair becomes evident from the following examples, wherein this is expressed numerically by the ditferences in alkali solubility and stretch or elongation. It should, however, be pointed out that these examples are given merely by way of illustration, not of limitation, and that numerous changes may be made in the details without departing from the splrit and the scope of the invention as hereinafter claimed.
  • EXAMPLE 1 As hair bleach, a 6 percent H 0 solution was employed in each instance whose pH was adjusted to 10 with ammonia shortly before application. Table 1 below shows, in the second column, the duration of the reaction period in minutes. Upon bleaching with the agents according to the invention (method 2, first column), the H 0 solution furthermore contained 0 .1 percent of a reaction product of phosphorous acid of the Formula 4:
  • B 0 percent lilkali stifubility was determined by a onehour exposure of the hair fiat 65 Gail. 0.1 n N aOH (aqueous), expressed in percent by weight.
  • 41,3 and C denotes hair of three diiierent; persons.
  • EXAMPLE -2 '8 parts by weight fatty alcohol and 7 parts by weight :of a fatty alcohol sulfate (chain length of both 16 to 18 @carbon atoms), and one part by weight fatty alcohol (chain length 12 to 14 carbon atoms) were heated to a .melt at 80 C. and emulsified with 34 parts by Weight - ⁇ water at that temperature.
  • l-aminobenzyl-1,1-diphosphonic acid in the form of its sodium salt were stirred into 100 g. of the cream, and this mixture evenly distributed on the ,hair to be bleached. Hair thus rendered blond distinguished itself by particular elasticity and mechanical qualities which by far surpassed average values.
  • EXAMPLE 4 An agent for bleaching hair blond was prepared by dissolving Parts of the condensation product of stearyl alcohol with 8 mols ethylene oxide 30 Parts paraflin oil Parts gycerol 10 Parts concentrated aqueous ammonia 4 Parts water 36
  • EXAMPLE 5 A hair bleaching agent in powder form was produced by mixing parts by weight alkyl sulfate, 50 parts by weight soda, -20 parts by weight sodium persulfate and 5 parts by weight of the compound having the Formula 5:
  • EXAMPLE 6 For dyeing oi -hair, 100 parts by weight of a dyeing (cream on the basis of customarily used oxidation dyes are mixed, shortly before application, with a solution of 0.2
  • a bleaching agent was produced in liquid form by dissolving 1 part by weight of a compound having the Formula 6:
  • a composition for the prevention of damage to hair upon dyeing and bleaching and for the improvement of gloss, elasticity and grip of said hair comprising substances selected from the group consisting of at least one oxidizing dye, a bleach, and mixtures thereof, plus 0.01 to 10 percent of a substance selected from the group consisting of phosphonic acid derivatives, their water-soluble methanol, ethanol, propanol, butanol, and amyl alcohol esters, and their sodium, potassium, ammonium, and
  • phosphonic acid derivatives having the formula wherein R and R individually are selected from the group consisting of hydrogen and an alkyl having 1 to 5 carbon atoms; X is selected from the group consisting of OH and --NH;; and R is selected from the group consisting of phenyl, a saturated aliphatic group having 1 to 5 carbon atoms, and the group having the configuration (
  • a process for the prevention of damage to hair upon bleaching and dyeing with oxidizing dyes and for the improvement of gloss, elasticity and grip of said hair which comprises rubbing into said hair, substantially at room temperature, a composition consisting of a carrier plus 0.01 to percent by weight of a compound selected from the group consisting of phosphonic acid derivatives, their waterssoluble methanol, ethanol, propanol, butanol, and amyl alcohol esters, and their sodium, potassium, ammonium, and ethanolamine salts; said phosphonic acid derivatives having the formula wherein R and R individually are selected from the group consisting of hydrogen and an alkyl having 1 to 5 carbon atoms; X is selected from the group consisting of -0H and NH and R is selected from the group consisting of phenyl, a saturated aliphatic group having 1 to 5 carbon atoms, and the group having the configuration References Cited by the Examiner FOREIGN PATENTS 6/57 Switzerland.

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  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
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Description

United States. Patent O 3,202,579 PHGSPHINIC ACID DERIVATIVES FOR PROTEC- TIQN OF HAIR FRQM DAMAGE IN BLEACHING AND DYEING THE SAME Peter Berth, Dusseldorf-Benrath, and Giinter Reese,
Dusseldorf, Germany, assignors to Therachemie Chemisch Therapeutische Gesellschaft rn.b.H., Dusseldorf, Germany No Drawing. Filed Sept. 19, 1963, Ser. No. 310,165 Claims priority, application Germany, Mar. 2, 1963, T 23,551 Claims. (Cl. 167-88) The invention relates to agents which prevent or, at least minimize, damage to hair, particularly human hair, when subjected to bleaching and dyeing operations.
For the purpose of dyeing and bleaching of hair, oxidizing substances have long been used, such as hydrogen peroxide, percarbamide, perborate, persulfate and other compounds emitting active oxygen. It is a well known fact that that oxidizing treatment, aside from destroying pigments in the hair, also attacks the fibrous substance of the hair itself. The damage thus inflicted manifests itself, e.g., in an increased alkali solubility and in a decrease of the mechanical properties of the hair, e.g., a strong decrease in its tear resistance, diminishing gloss and grip and increasing brittleness.
It now has been found that damage to hair upon bleaching and dyeing with active oxygen can largely be averted when the agents hereinafter described are employed. These agents are characterized by a content of compositions having the following formulae:
wherein X represents either OH or -NH R is an aryl radical or an aliphatic radical having 1 to 5 carbon atoms, or the radical R2 (la) and wherein R and R respectively, denote individually, in Formula 1 as well as in Formula 1a, a hydrogen atom or an alkyl radical having 1 to 5 carbon atoms. Also applicable, in lieu of the compounds shown as (1) and (1a), respectively, are their Water-soluble salts. Compounds of the composition (2), which is one embodiment of Formula 1 above,
can be produced by several methods known per se. For instance, phosphorous acid can be reacted with carboxylic acid chlorides or carboxylic acid anhydrides or with mixtures of both such compounds to yield these compounds. Readily available in large scale production are reaction products of phosphorous acid with acetyl chloride and/ or acetic anhydride. Finally, in lieu of the carboxylic acid chlorides and phosphorous acid, phosphorous trichloride and carboxylic acids can be used in suitable stoichiometrical proportions. Depending on the method of production, pure single products or mixtures of pure products are obtained.
Instead of the acid reaction products named in the 3,202,579 Patented Aug. 24, 1955 formulae above, frequently their corresponding alkali salts, e.g., sodium, potassium, ammonium salts, and also their ethanolamine salts are used in practice, which are produced by neutralization of the acids. Likewise, the water-soluble esters are suited for the purposeat hand, produced by partial esterification of the hydroxyl groups with methanol, ethanol, propanol, butanol or amyl alcohol.
Production of the compounds named above having the Formula 3, another embodiment of Formula 1 above, i.e.,
is accomplished by the reaction of phosphorus trihalides with organic nitriles or with malonic acid dinitiile, respectively, whereby substantially 2 mols PCl are to be applied to each mol nitrile. The reaction product then is hydrolized to the free acid which, subsequently, can be converted into the corresponding salts or esters, as above.
The compounds named above can be used singularly or as mixtures of the different substance named.
According to the invention, the materials named can be employed on carrier substances or can be admixed to a solution, a gel, a cream or a powder, or else they may be used in combination with the oxidizing agent. Furthermore, they can be incorporated in a treating agent, such as a rinse or a hair wash. The damage-preventing substances are applied in quantities of 0.01 to 10 percent by weight, calculated on the agent in which incorporated, and preferably in amounts of 0.1 to 2 percent by weight. If desired, larger amounts can be used, although this does not have any practical advantages.
The hair treating agents containing the damage-preventing substances also may contain, if desired, further customary additives, such as perfume oils, dyestuffs, thickeners, fatty alcohols, anionactive and cationactive and nonionic wetting agents. Particularly suitable thickeners are cellulose derivatives, polyvinylpyrrolidone, polyacrylates, alginates and, in certain instances, fatty alcohols. Suitable Wetting agents include fatty alcohol sulfates, alkyl sulfates and condensation products of fatty alcohols with ethylene oxide, whereby the alkyl radical in all instances has a chain length of 12 to 18 carbon atoms. Also usable are alkylbenzenesulfates and alkylpyridinium salts.
Hair treated with the agents according to the invention are distinguished by high gloss, improved hand or grip and especially good elasticity, as compared to hair which had been treated in the usual manner under equal conditions. The difference in damage to the hair becomes evident from the following examples, wherein this is expressed numerically by the ditferences in alkali solubility and stretch or elongation. It should, however, be pointed out that these examples are given merely by way of illustration, not of limitation, and that numerous changes may be made in the details without departing from the splrit and the scope of the invention as hereinafter claimed.
EXAMPLE 1 As hair bleach, a 6 percent H 0 solution was employed in each instance whose pH was adjusted to 10 with ammonia shortly before application. Table 1 below shows, in the second column, the duration of the reaction period in minutes. Upon bleaching with the agents according to the invention (method 2, first column), the H 0 solution furthermore contained 0 .1 percent of a reaction product of phosphorous acid of the Formula 4:
This substance had been produced according 6 the process dlSClS6d lIl JACS 34, 492-499 The alkali solubility of the hair, expressed in percen' L Weight, was determined according to the method of H. Freytag, Parfumerie und Kosmetik 41 Nr.
I (1960), 405 (a German publicanon) The alkali solubility of entirely untreated hair lies between 2 arl 6 Percent,
Table 1 iALKALI 'SOLUBI'LITY 1 Treating Kind of Hair 2 Average Method ime Alkali (minutes) Solubility,
B 0 percent lilkali stifubility was determined by a onehour exposure of the hair fiat 65 Gail. 0.1 n N aOH (aqueous), expressed in percent by weight.
41,3 and C denotes hair of three diiierent; persons.
EXAMPLE -2 '8 parts by weight fatty alcohol and 7 parts by weight :of a fatty alcohol sulfate (chain length of both 16 to 18 @carbon atoms), and one part by weight fatty alcohol (chain length 12 to 14 carbon atoms) were heated to a .melt at 80 C. and emulsified with 34 parts by Weight -\water at that temperature. The cream obtained after (cooling was adjusted to a pH of 10.0 by addition of 4 :parts by weight concentrated ammonia and made up to 100 parts with water. For the purpose of bleaching hu- :man hair blond, 30 g. of a mixture of 28 g. melamine 'perhydrate and 2 g. l-aminobenzyl-1,1-diphosphonic acid in the form of its sodium salt were stirred into 100 g. of the cream, and this mixture evenly distributed on the ,hair to be bleached. Hair thus rendered blond distinguished itself by particular elasticity and mechanical qualities which by far surpassed average values.
Equally good results were obtained by adding initially to the cream 2 g. l-aminobenzyl-l,l-diphosphonic acid or 2 g. hydroxybenzyl-l,l-diphosphonic acid in the form of their sodium salts.
EXAMPLE 4 An agent for bleaching hair blond was prepared by dissolving Parts of the condensation product of stearyl alcohol with 8 mols ethylene oxide 30 Parts paraflin oil Parts gycerol 10 Parts concentrated aqueous ammonia 4 Parts water 36 EXAMPLE 5 A hair bleaching agent in powder form was produced by mixing parts by weight alkyl sulfate, 50 parts by weight soda, -20 parts by weight sodium persulfate and 5 parts by weight of the compound having the Formula 5:
in the form of its sodium salt, whereby X selectively denotes, with equally good result, either -NH or OH.
15 Damage to the hair upon bleabhing with such a product is reduced to a considerabie extent as compared to an equal treatment but without the reaction product of phosphorous acid.
EXAMPLE 6 For dyeing oi -hair, 100 parts by weight of a dyeing (cream on the basis of customarily used oxidation dyes are mixed, shortly before application, with a solution of 0.2
, part by weight of the reaction compound of phosphorous 25 acid, Formula 4 (see Example 1) in parts by weight of 6 percent aqueous H 0 I Hair dyed with this mixture has exceptional gloss and grip. The rate of damage to the .hair is considerably less than that when the reaction product of phosphorous 39 acid is omitted from the otherwise like agent.
A bleaching agent was produced in liquid form by dissolving 1 part by weight of a compound having the Formula 6:
5o otherwise the same conditions:
, 0 51111 0 "no-i i -on (in r m, (in "(7) EXAMPLE 8 Prior to bleaching, the hair was rinsed with a solution containing 10 parts by weight of compound Formula 4 (see Example 1), in the form o'f'its potassium salt, and
(my 10 parts by weight cetyltrirnethylammoniumchloride per 100 parts by weight water. Thereafter, bleaching was carried out in the customary manner with an H 0 solution. The hair thus treated exhibited considerably better elasticity than hair which had not been rinsed with 5.: the above solution prior to bleaching in the same manner.
What is claimed is:
1. A composition for the prevention of damage to hair upon dyeing and bleaching and for the improvement of gloss, elasticity and grip of said hair, comprising substances selected from the group consisting of at least one oxidizing dye, a bleach, and mixtures thereof, plus 0.01 to 10 percent of a substance selected from the group consisting of phosphonic acid derivatives, their water-soluble methanol, ethanol, propanol, butanol, and amyl alcohol esters, and their sodium, potassium, ammonium, and
ethanolamine salts; said phosphonic acid derivatives having the formula wherein R and R individually are selected from the group consisting of hydrogen and an alkyl having 1 to 5 carbon atoms; X is selected from the group consisting of OH and --NH;; and R is selected from the group consisting of phenyl, a saturated aliphatic group having 1 to 5 carbon atoms, and the group having the configuration (|)Bs O=P-OH CHz -X O=POH 2. A process for the prevention of damage to hair upon bleaching and dyeing with oxidizing dyes and for the improvement of gloss, elasticity and grip of said hair, which comprises rubbing into said hair, substantially at room temperature, a composition consisting of a carrier plus 0.01 to percent by weight of a compound selected from the group consisting of phosphonic acid derivatives, their waterssoluble methanol, ethanol, propanol, butanol, and amyl alcohol esters, and their sodium, potassium, ammonium, and ethanolamine salts; said phosphonic acid derivatives having the formula wherein R and R individually are selected from the group consisting of hydrogen and an alkyl having 1 to 5 carbon atoms; X is selected from the group consisting of -0H and NH and R is selected from the group consisting of phenyl, a saturated aliphatic group having 1 to 5 carbon atoms, and the group having the configuration References Cited by the Examiner FOREIGN PATENTS 6/57 Switzerland.
OTHER REFERENCES Leibigs Annalen der Chemie, vol. 623, page 103 1953 JULIAN S. LEVITT, Primary Examiner.

Claims (1)

1. A COMPOSITION FOR THE PREVENTION OF DAMAGE TO HAIR UPON DYEING AND BLEACHING AND FOR THE IMPROVEMENT OF GLOSS, ELASTICITY AND GRIP OF SAID HAIR, COMPRISING SUBSANCES SELECTED FROM THE GROUP CONSISTING OF AT LEAST ONE OXIDIZING DYE, A BLEACH, AND MIXTURES THEREOF, PLUS 0.01 TO 10 PERCENT OF A SUBSTANCE SELECTED FROM THE GROUP CONSISTING OF PHOSPHONIC ACID DERIVATIVES, THEIR WATER-SOLUBLE METHANOL, ETHANOL, PROPANOL, BUTANOL, AND AMYL ALCOHOL ESTER, AND THEIR SODIUIM, POTASSIUM, AMMONIUM, AND ETHANOLAMINE SALTS; SAID PHOSPHONIC ACID DERIVATIVES HAVING THE FORMULA
US310165A 1963-03-02 1963-09-19 Phosphinic acid derivatives for protection of hair from damage in bleaching and dyeing the same Expired - Lifetime US3202579A (en)

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DET23551A DE1202441B (en) 1963-03-02 1963-03-02 Means for reducing the damage to hair during bleaching and dyeing
GB21887/63A GB990660A (en) 1963-03-02 1963-05-31 Improvements in and relating to the bleaching and dyeing of hair

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DE (1) DE1202441B (en)
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Cited By (30)

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US3400148A (en) * 1965-09-23 1968-09-03 Procter & Gamble Phosphonate compounds
US3400176A (en) * 1965-11-15 1968-09-03 Procter & Gamble Propanepolyphosphonate compounds
US3400151A (en) * 1967-12-28 1968-09-03 Procter & Gamble Bicyclic dimer of ethane-1-hydroxy-1, 1-diphosphonic acid and salts thereof
US3400150A (en) * 1965-07-29 1968-09-03 Procter & Gamble Process for preparing hydroxydiphosphonic acids from elemental phosphorous, oxygen and carboxylic acids
US3400147A (en) * 1965-03-30 1968-09-03 Procter & Gamble Process for preparation of organophosphorous compounds
US3496222A (en) * 1967-12-28 1970-02-17 Procter & Gamble Diacetylated cyclic dimer of ethane-1-hydroxy - 1,1 - diphosphonic acid and salts thereof
US3846420A (en) * 1969-11-19 1974-11-05 Henkel & Cie Gmbh Process for the preparation of 1-aminoalkane-1,-diphosphonic acids and their salts
US3870750A (en) * 1969-11-19 1975-03-11 Henkel & Cie Gmbh Process for the production of aminomethane-diphosphonic acid and its salts
US3954393A (en) * 1973-08-29 1976-05-04 Combe, Inc. Hair dyeing composition containing bismuth citrate, triethanolamine and sulfur
US3959360A (en) * 1975-07-31 1976-05-25 Monsanto Company Process for preparing 1-hydroxy, ethylidene-1,1-diphosphonic acid
US4138478A (en) * 1975-11-04 1979-02-06 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Agents for reducing the damage to hair during bleaching and dyeing
US4195972A (en) * 1978-10-20 1980-04-01 Combe Incorporated Aqueous-based hair dyeing composition containing a soluble bismuth salt and a reducing compound
US4306873A (en) * 1978-10-20 1981-12-22 Combe Incorporated Aqueous-based hair dyeing composition containing a soluble bismuth salt complex and a reducing compound
US4608368A (en) * 1984-07-13 1986-08-26 Henkel Kommanditgesellschaft Auf Aktien 1-hydroxy-1,1-diphosphonic acids and cytostatic use thereof
US5021324A (en) * 1990-10-05 1991-06-04 Polychrome Corporation Printing plate protectant
US5438048A (en) * 1990-12-20 1995-08-01 Leiras Oy Methylenebisphosphonic acid derivatives
US20040055095A1 (en) * 2001-03-20 2004-03-25 The Procter & Gamble Company Oxidizing compositions comprising a phosphonic acid type chelant and a conditioning agent and methods of treating hair
US6732744B2 (en) 2001-12-07 2004-05-11 The Procter & Gamble Company Method for the ultrasonic treatment of hair and other keratinous fibers
US20040123402A1 (en) * 2001-03-20 2004-07-01 The Procter & Gamble Company Oxidizing compositions comprising a chelant and a conditioning agent and methods of treating hair
US20070107143A1 (en) * 2001-03-20 2007-05-17 The Procter & Gamble Company Oxidative treatment of hair with reduced hair damage
US20070118999A1 (en) * 2001-03-20 2007-05-31 The Procter & Gamble Company Compositions suitable for the treatment of hair comprising chelants and methods for reducing oxidative hair damage
CN100396272C (en) * 2001-03-20 2008-06-25 宝洁公司 Oxidative treatment of hair with reduced hair damage
US20090119852A1 (en) * 2007-11-05 2009-05-14 Jennifer Mary Marsh Oxidizing Hair Colourant Compositions
WO2015191343A1 (en) 2014-06-12 2015-12-17 The Procter & Gamble Company System and methods of detecting and demonstrating ultraviolet damage to hair via evaluation of protein fragments
EP2488150B1 (en) * 2009-10-13 2018-11-21 L'Oréal Composition including a glyceride and an organophosphonic acid or one of the salts thereof, dyeing or colour-lightening method implementing same and devices
WO2019032805A1 (en) 2017-08-11 2019-02-14 Sytheon Limited Hair treatment compositions and methods
WO2023222789A1 (en) 2022-05-18 2023-11-23 L'oreal Device for treating human keratin materials
WO2023222781A1 (en) 2022-05-18 2023-11-23 L'oreal Device for treating the hair, and method
WO2023222788A1 (en) 2022-05-18 2023-11-23 L'oreal Method for cleansing human keratin materials
FR3135604A1 (en) 2022-05-18 2023-11-24 L'oreal Device for treating human keratin materials

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GB1392284A (en) 1971-03-30 1975-04-30 Unilever Ltd Stabilisation of active oxygen releasing compounds
DE2549293C2 (en) * 1975-11-04 1985-05-30 Henkel KGaA, 4000 Düsseldorf Preparations for reducing the damage to hair during bleaching and dyeing
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Cited By (34)

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US3400147A (en) * 1965-03-30 1968-09-03 Procter & Gamble Process for preparation of organophosphorous compounds
US3400150A (en) * 1965-07-29 1968-09-03 Procter & Gamble Process for preparing hydroxydiphosphonic acids from elemental phosphorous, oxygen and carboxylic acids
US3400148A (en) * 1965-09-23 1968-09-03 Procter & Gamble Phosphonate compounds
US3400176A (en) * 1965-11-15 1968-09-03 Procter & Gamble Propanepolyphosphonate compounds
US3400151A (en) * 1967-12-28 1968-09-03 Procter & Gamble Bicyclic dimer of ethane-1-hydroxy-1, 1-diphosphonic acid and salts thereof
US3496222A (en) * 1967-12-28 1970-02-17 Procter & Gamble Diacetylated cyclic dimer of ethane-1-hydroxy - 1,1 - diphosphonic acid and salts thereof
US3846420A (en) * 1969-11-19 1974-11-05 Henkel & Cie Gmbh Process for the preparation of 1-aminoalkane-1,-diphosphonic acids and their salts
US3870750A (en) * 1969-11-19 1975-03-11 Henkel & Cie Gmbh Process for the production of aminomethane-diphosphonic acid and its salts
US3954393A (en) * 1973-08-29 1976-05-04 Combe, Inc. Hair dyeing composition containing bismuth citrate, triethanolamine and sulfur
US3959360A (en) * 1975-07-31 1976-05-25 Monsanto Company Process for preparing 1-hydroxy, ethylidene-1,1-diphosphonic acid
US4138478A (en) * 1975-11-04 1979-02-06 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Agents for reducing the damage to hair during bleaching and dyeing
US4195972A (en) * 1978-10-20 1980-04-01 Combe Incorporated Aqueous-based hair dyeing composition containing a soluble bismuth salt and a reducing compound
US4306873A (en) * 1978-10-20 1981-12-22 Combe Incorporated Aqueous-based hair dyeing composition containing a soluble bismuth salt complex and a reducing compound
US4608368A (en) * 1984-07-13 1986-08-26 Henkel Kommanditgesellschaft Auf Aktien 1-hydroxy-1,1-diphosphonic acids and cytostatic use thereof
US5021324A (en) * 1990-10-05 1991-06-04 Polychrome Corporation Printing plate protectant
US5438048A (en) * 1990-12-20 1995-08-01 Leiras Oy Methylenebisphosphonic acid derivatives
US20040055095A1 (en) * 2001-03-20 2004-03-25 The Procter & Gamble Company Oxidizing compositions comprising a phosphonic acid type chelant and a conditioning agent and methods of treating hair
US20040123402A1 (en) * 2001-03-20 2004-07-01 The Procter & Gamble Company Oxidizing compositions comprising a chelant and a conditioning agent and methods of treating hair
US20070107143A1 (en) * 2001-03-20 2007-05-17 The Procter & Gamble Company Oxidative treatment of hair with reduced hair damage
US20070118999A1 (en) * 2001-03-20 2007-05-31 The Procter & Gamble Company Compositions suitable for the treatment of hair comprising chelants and methods for reducing oxidative hair damage
CN100396272C (en) * 2001-03-20 2008-06-25 宝洁公司 Oxidative treatment of hair with reduced hair damage
US6732744B2 (en) 2001-12-07 2004-05-11 The Procter & Gamble Company Method for the ultrasonic treatment of hair and other keratinous fibers
US20090119852A1 (en) * 2007-11-05 2009-05-14 Jennifer Mary Marsh Oxidizing Hair Colourant Compositions
EP2103299A2 (en) 2007-11-05 2009-09-23 The Procter and Gamble Company Oxidizing hair colourant compositions
US7597720B2 (en) 2007-11-05 2009-10-06 The Procter & Gamble Company Oxidizing hair colourant compositions
EP2488150B1 (en) * 2009-10-13 2018-11-21 L'Oréal Composition including a glyceride and an organophosphonic acid or one of the salts thereof, dyeing or colour-lightening method implementing same and devices
WO2015191343A1 (en) 2014-06-12 2015-12-17 The Procter & Gamble Company System and methods of detecting and demonstrating ultraviolet damage to hair via evaluation of protein fragments
WO2019032805A1 (en) 2017-08-11 2019-02-14 Sytheon Limited Hair treatment compositions and methods
WO2023222789A1 (en) 2022-05-18 2023-11-23 L'oreal Device for treating human keratin materials
WO2023222781A1 (en) 2022-05-18 2023-11-23 L'oreal Device for treating the hair, and method
WO2023222788A1 (en) 2022-05-18 2023-11-23 L'oreal Method for cleansing human keratin materials
FR3135605A1 (en) 2022-05-18 2023-11-24 L'oreal Process for cleaning human keratin materials
FR3135604A1 (en) 2022-05-18 2023-11-24 L'oreal Device for treating human keratin materials
FR3135603A1 (en) 2022-05-18 2023-11-24 L'oreal Hair treatment device and method

Also Published As

Publication number Publication date
CH440557A (en) 1967-07-31
DE1202441B (en) 1965-10-07
NL146707B (en) 1975-08-15
NL6401994A (en) 1964-09-03
FI42858B (en) 1970-08-03
GB990660A (en) 1965-04-28
LU45568A1 (en) 1965-03-02
AT245734B (en) 1966-03-10
BE644474A (en) 1964-08-28

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