US3908672A - Novel process for improving and modifying the properties of hair - Google Patents

Novel process for improving and modifying the properties of hair Download PDF

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Publication number
US3908672A
US3908672A US449432A US44943274A US3908672A US 3908672 A US3908672 A US 3908672A US 449432 A US449432 A US 449432A US 44943274 A US44943274 A US 44943274A US 3908672 A US3908672 A US 3908672A
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hair
temperature
minutes
treatment
composition
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US449432A
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English (en)
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Pierre Bore
Jean-Claude Arnaud
Gregoire Kalopissis
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LOreal SA
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LOreal SA
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/04Preparations for permanent waving or straightening the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients

Definitions

  • the present invention has for its object a novel process for improving and modifying the properties of hair, in particular living human hair.
  • Such a treatment is performed in a known way on wool but it cannot be used directly to treat living human hair.
  • Hair having undergone this transformation called lanthionization has a different composition and structure from that of normal hair, which gives it interesting new properties.
  • lanthionized hair shows a great elasticity when it is in the wet state.
  • lanthionized hair is subjected to combing in the wet state, for example after shampooing. Then it has been found that lanthionized hair is much more resistant to breaking and that a number of hairs broken during such an operation is clearly less than that of natural hairs, i.e., unlanthionized.
  • the number of hairs broken in the wet state is less than half the number of hairs broken in the case of natural hairs.
  • This characteristic of lanthionized hair means that, after setting, this hair, in an atmosphere of normal relative humidity, resumes its initial form less rapidly than untreated hair.
  • hair subjected to lanthionization according to the process of the invention presents a greater permeability to hair treating agents than untreated hair.
  • This improved permeability generally facilitates all capillary treatments, in particular dyeing operations, whether direct dyeing or oxidation dyeing is involved, and bleaching operations.
  • dyeing and bleaching are realized more easily and rapidly than in the case of untreated hair and, in addition, the intensity of the coloring is improved.
  • alkaline solubility is meant the loss of weight by putting in the presence of an N/4 sodium hydroxide solution at a temperature of 65C.
  • lanthionization of hair gives it irreversible properties which it keeps during its entire life. This is particularly the case for better holding of a setting which is retained for all successive settings, without it being necessary to use any additional prod uct, even if these later settings are simply done with water.
  • the process consists of submitting to a lanthionization treatment human hair that is subjected, to an extension by mechanical deformation.
  • This mechanical deformation is able to be realized by either a longitudinal stretching (for example a smoothing, by uncurling, with the aid of a comb) or by rolling about curlers or hair setting rol lers.
  • one subjects the hair to an extension by mechanical deformation, treatitng it in an aqueous medium with a composition having a pH of between about 10.5 and 13, for a sufficient time to obtain the desired proportion of lanthionine, keeping the hair in the wet state during the entire treatment.
  • the treatment is generally effectuated on hair subjected to an extension by a mechanical deformation corresponding to a stretching of the order of l to 3%, and preferably from 1 to 2% of wet hair.
  • This stretching is able to be obtained by either rolling the hair on curlers or on hair setting rollers, or in subjecting the hair to a decurling by combing, that is to say, a mechanical smoothing of the hair with the aid of a comb.
  • compositions utilized in the process defined hereinabove are preferably hydroxide bases of the alkali metals or alkaline earth metals.
  • One is able in par ticular to utilize Ca(OH) LiOH, NaOH, KOH, or their mixtures, without this listing being limiting.
  • the molar concentration of these alkali or alkaline earth metal hydroxides is determined by the desired value of the pH, which should be between 10.5 and 13.
  • the above process should be practiced at a sufficiently high temperature so that the treatment period is not too long, this temperature, however, being bearable by the hair.
  • the treatment is effectuated at a temperature between about 25 to 30 and 120C.
  • the period of treatment which is a function of the proportion of the lanthionine desired, varies according to the treatment conditions, and particularly according to the composition used, and the temperature, as will be explained in detail below.
  • the period of treatment can vary from a few minutes to a few hours, but, for practical reasons, the characteristics of the process of the present invention have been selected so that the treatment period is not less than five minutes, or preferably, about ten minutes, and is not greater than about 60 minutes.
  • the proportion of lanthionization which is obtained by the treatment according to the invention depends on the different characteristics of the treatment.
  • the increase of temperature also plays a role in the sense of an increase in the degree of lanthionization.
  • the degree of lanthienization is generally higher than when applying the process to hair previously wetted.
  • the pH or the temperature may thus be lowered.
  • an effort should not be made to exceed a degree of lanthionization of 50%, which seems to constitute an optimum result for natural hair, that is to say, hair not having previously undergone permanent deformation treatment or bleaching, otherwise the hair is degraded without an increase in its degree of lanthionization.
  • the period of temperature of treatment, or the pH of the composition should be reduced, for example, it would be possible to use compositions having a pH of 10.5 to 12, at a temperature between about 25 to 30C and 50C for a period between 5 and 20 to 30 minutes.
  • the hair is subjected to a mechanical deformation, treating it in an aqueous medium with a composite of a hydroxide base of an alkali or alkaline earth metal having a pH between 12.5 and 13, at a temperature between 30 and 120C, for a sufficient time to obtain the desired degree of lanthionine, this time being between about 5 and 60 minutes.
  • the treatment time should be longer than in the case of a composition in gel or cream form, if it is desired to obtain a comparable degree of lanthionization.
  • a particular example illustrating this phenomena will be given further on.
  • hydroxide giving the composition its pH between about 12.5 and 13 does not have a critical influence on the treatment according to the invention.
  • hydroxides Ca(OI-l) LiOH, NaOH, KOH, or their mixtures without this list being limiting.
  • the molar concentration of the alkali or alkaline earth metal hydroxides or their mixtures in the composition is determined by the desired value of the pH of the composition, which should be between 12.5 and 13.
  • the particular operating conditions according to the first embodiment of the invention as a function of the temperature at which it is desired to operate can be made precise as indicated below.
  • the treatment period When operating between 30 and 50C (preferably between 40 and 50C), the treatment period must be of the order of 20 to 60 minutes. However, if the composition is a simple aqueous solution with an alkaline base, the treatment period should be at least 30 to 40 minutes.
  • the treatment period When operating between 50 and C, the treatment period must be of the order of 10 to 50 minutes.
  • the treatment period When operating between 80 and C, the treatment period must be of the order of 5 to 20 minutes.
  • compositions having an alkali or alkaline earth metal hydroxide base but, in addition, comprising particular substances which have the effect of making it possible to reduce the time, temperature, and/or the pH of the treatment.
  • these substances will be designated as lanthionization activator.
  • one subjects the hair to a mechanical deformation, treating them in an aqueous medium with the aid of a composition having a pH between about 10.5 and 13, at a temperature between 30 and 120C, for a sufficient period to obtain the desired degree of lanthionization, this period being about 5 to 60 minutes, said composition having an alkali metal or alkaline earth metal hydroxide base and containing a lanthionization activator selected from the group consisting of electrolytes that are neutral from an oxidation-reduction standpoint, reducing agents having a limited hydrolytic action on the S-S bonds on the cystine, and cationic surfactants.
  • the alkali or alkaline earth metal hydroxides that can be used in the second embodiment of the process of the invention are particularly Ca(OI-I) LiOH, NaOH, KOH, or their mixtures. Their concentration is a func tion of the desired value of the pH which must be between 10.5 and 13.
  • the neutral electrolytes from an oxidation-reduction standpoint can be inorganic electrolytes, such as alkali halides, such as, for example, sodium chloride or lithium bromide, the alkaline earth halides such as calcium chloride, or the alkali or alkaline earth sulfates such as sodium, potassium, or calcium sulfate. They are preferably utilized in a concentration of up to 5 moles per liter.
  • alkali halides such as, for example, sodium chloride or lithium bromide
  • the alkaline earth halides such as calcium chloride
  • alkali or alkaline earth sulfates such as sodium, potassium, or calcium sulfate.
  • the electrolytes neutral from an oxidation-reduction standpoint, can also be organic electrolytes such as guanidine carbonate, and are preferably used in a concentration of up to one mole per liter.
  • the reducing agents having a limited hydrolytic action on the SS bonds of the cystine can include, for example, alkali or alkaline earth sulfides, in a concentration up to 3 X 2 moles per liter or alkali or alkaline earth sulfites at a concentration between 10 3 and 10 1 moles per liter.
  • the activators made up of cationic surface active compounds, can include, for example, cetyltrimethylammonium bromide (known under the trademark Cetavlon) at a concentration of up to 3 X 10 2 moles per liter, or a quaternary ammonium hydroxide such as that known as Hyamine 10 X, at a concentration of up to 10 1 moles per liter.
  • cetyltrimethylammonium bromide known under the trademark Cetavlon
  • Hyamine 10 X quaternary ammonium hydroxide
  • the treatment of the hair can give rise to different modes of execution, depending upon the temperature of the treatment.
  • one is able, for example, to roll the hair subjecting it to an extension by mechanical deformation as indicated above, on heated curlers.
  • One is equally able to operate without heating, that is to say, in practice between 30 to 35 and 40C.
  • the treatment period When operating between 30 and 50C, the treatment period must be of the order of 15 to 60 minutes.
  • the treatment period When operating between 50 and C, the treatment period must be between 5 and 10 minutes and 40 minutes.
  • the treatment period When operating between 80 and C, the treatment period must be between 5 and 20 minutes.
  • compositions used according to the invention are advantageous in gel or cream form, with sufficient consistency for the composition to be retained naturally on the hair. In this way there is prevented a considerable evaporation of the aqueous phase, which should be retained in order to assure practice of the process according to the invention. Actually, according to the invention, it is necessary that the hair be kept in the wet state during the entire treatment period.
  • the cream or gel should be such that the aqueous phase containing the active substances can come into contact and assure impregnation of the hair.
  • emulsions constituting the composition are preferably of the oin-in-water type.
  • compositions according to the present invention are prepared according to the usual methods.
  • adjuvants usually used in creams or gels particularly, polyoxyethylene glycols; other polyethers such as nonyphhenol polyethoxyethers; fatty acids such as oleic acid; fatty alcohols such as oleyl alcohol; hydroxyethyl cellulose; etc.
  • the alkaline composition which makes it possible to achieve the transformation of cystine into lanthionine should not contain alcohol or only contain a slight alcohol content (preferably less than 10%) because the presence of alcohol increases the alkaline solubility of the hair.
  • the treatment according to this invention is clearly distinguished from standard processes of hair treatment such as those which are used for permanent deformations, oxidizing, dyeing, or bleachings, because these treatments are always carried out under conditions different from those according to the invention, and they practically always take place in a medium that is both alkaline and oxidizing.
  • Keratocystine Keratocystine
  • K-S-K lanthionine
  • K-SOOK oxdizing agents
  • Hair treated according to the invention shows, after having undergone a hydrochloric hydrolysis, a degree of lanthionine which remains unchanged and which is always reproducible under precise dosing conditions.
  • degree of lanthionization The degree isequal to the percentage of initial cystine bonds of the natural hair transformed into lanthionine bonds during the treatment.
  • the hair is hydrolyzed with 5 ml of 5.6 N (azeotrope) hydrochloric acid in a sealed test tube. It is left in an oven at 120C for 4 hours with agitation.
  • 5.6 N azeotrope
  • the tube is opened and the hydrolysate is brought to dryness in a rotary evaporator at 35C under vacuum.
  • the residue is dissolved with ml of distilled water and again dried.
  • a control deposit of 0.05 ml is made, in two shallow dishes, of the standard solution containing 2.5 moles per ml of each amino acid and in particular lanthionine.
  • K represents the amount (in g) of each amino acid present in g of hair MW is the molecular weight of the amino acid considered Sa is the sampling in mg of hair 3.
  • degree of lanthionization The amount of cystine present in the average undegraded hair is 16%.
  • the rate of lanthionization was determined as indicated above.
  • the relative humidity set at 65% is obtained with a saturated solution of sodium nitrite.
  • Drying is for 2 hours in an oven at 60C.
  • the uncurling is followed by watching the end of the locks which uncurl in front of a stiff sheet of paper marked off in millimeters. Each series of measurements is made in comparison with a control lock (untreated natural hair).
  • Readings are made every 5 minutes for 2 hours and 30 minutes. A final reading is made after 16 hours.
  • Hydroxyethyl cellulose WP 4400 4 g Hydrated lithium oxide (LiOH, H O) 2 g Potassium sulfate (K 80 17.4 g Water sufficient for 100 g pI-I gel: 12.7
  • Hydroxyethyl cellulose WP 4400 4 g Hydrated lithium oxide (LiOI-I,H O) 2 g Sodium chloride (NaCl) 17.5 g Water sufficient for 100 g pH gel: 1 1.7
  • Hydroxyethyl cellulose WP 4400 4 g Sodium hydroxide (NaOH) g Water sufficient for g pH gel: l2.6 Use:
  • riydroxyethyl cellulose WP 4400 4 g Hydrated lithium oxide (LiOH, H 2 g Cetavlon 10 g Water sufficient for 100 g pH gel: 12.4 Use:
  • Hydroxyethyl cellulose WP 4400 4 g Hydrated lithium oxide (LiOH, H 0) 2 g Lithium bromide (LiBr) 34.8 g Water sufficient for 100 g pH gel: l0.5 Use:
  • Hydroxyethyl cellulose WP 4400 4 g Hydrated lithium oxide (LiOH. H O) L25 g Guanidine carbonate l8 g Water sufficient for 100 g pH gel: l2.6 Use:
  • a process for improving and modifying the properties of living human hair which comprises subjecting the hair to a stretching by mechanical deformation and treating said hair in an aqueous medium with a composition consisting essentially of an alkali or alkaline earth metal hydroxide base and having a pH between about 10.5-and 13 for a time sufficient to convert about 10 to 50% of the cystine of the hair into lanthionine, while maintaining the hair in the wet state during the treatment.
  • composition also contains a lanthionization activator selected from the group consisting of electrolytes that are neutral from an oxidation-reduction standpoint; reducing agents having a limited hydrolytic action on the S-S bonds of cystine; and cationic surfactant compounds; said treatment being carried out for about 5 to 60 minutes at a temperature between 30-l20C.
  • a lanthionization activator selected from the group consisting of electrolytes that are neutral from an oxidation-reduction standpoint; reducing agents having a limited hydrolytic action on the S-S bonds of cystine; and cationic surfactant compounds; said treatment being carried out for about 5 to 60 minutes at a temperature between 30-l20C.
  • electrolytes are inorganic electrolytes and are present at a concentration of up to 5 moles per liter.
  • electrolytes are organic electrolytes and are present at a concentration of up to one mole per liter.
  • reducing agents are alkali or alkaline earth metal sulfides and are present at a concentration of up to 3 X 10 moles per liter.
  • composition contains at least one hydroxide selected from the group consisting of calcium hydroxide, lithium hydroxide, sodium hydroxide, and potassium hydroxide.
  • composition is in the form of a gel or a cream containing an oil-inwater emulsion.
  • a process for improving and modifying the properties of living human hair which comprises subjecting utes at a temperature between 30 and C.

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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)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
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US449432A 1973-03-08 1974-03-08 Novel process for improving and modifying the properties of hair Expired - Lifetime US3908672A (en)

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LU67178A LU67178A1 (de) 1973-03-08 1973-03-08

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US05/449,437 Expired - Lifetime US3971391A (en) 1973-03-08 1974-03-08 Process for improving the quality of living, human hair by lanthionization

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US (2) US3908672A (de)
JP (2) JPS5029756A (de)
AR (1) AR204622A1 (de)
AT (2) AT342207B (de)
BE (2) BE811911A (de)
BR (1) BR7401728D0 (de)
CA (2) CA1041428A (de)
CH (2) CH591859A5 (de)
DE (2) DE2410678A1 (de)
ES (2) ES423990A1 (de)
FR (2) FR2220243B1 (de)
GB (2) GB1466622A (de)
IT (2) IT1055551B (de)
LU (1) LU67178A1 (de)
NL (2) NL7403048A (de)

Cited By (16)

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Publication number Priority date Publication date Assignee Title
US4992267A (en) * 1988-04-28 1991-02-12 Johnson Products Co., Inc. Hair straightening composition and system
US20020159962A1 (en) * 2001-02-22 2002-10-31 Cannell David W. Hair relaxer compositions comprising at least one hydroxide compound and at least one activating agent, and methods of using the same
US20020189027A1 (en) * 2001-04-20 2002-12-19 Cannell David W. Composition and methods for lanthionizing keratin fibers using at least one organic nucleophile and at least one hydroxide ion generator
US20030037384A1 (en) * 2001-08-20 2003-02-27 Nguyen Nghi Van Compositions comprising at least one hydroxide compound and at least one oxidizing agent, and methods to straighten curly hair
WO2003015725A2 (en) * 2001-08-20 2003-02-27 L'oreal S.A. Compositions comprising at least one hydroxide compound and at least one reducing agent, and methods for relaxing hair
US20050125914A1 (en) * 2003-11-18 2005-06-16 Gerard Malle Hair shaping composition comprising at least one- non-hydroxide base
US20050129645A1 (en) * 2003-11-18 2005-06-16 L'oreal Hair shaping composition comprising at least one non-hydroxide imine
US20050136018A1 (en) * 2003-11-18 2005-06-23 Gerard Malle Hair relaxing composition comprising at least one secondary or tertiary amine
US20050136017A1 (en) * 2003-11-18 2005-06-23 Gerard Malle Hair relaxing composition comprising at least one non-hydroxide imine
US20050136019A1 (en) * 2003-11-18 2005-06-23 Gerard Malle Hair shaping composition comprising at least one amine chosen from secondary and tertiary amines
US20050136016A1 (en) * 2003-11-18 2005-06-23 Gerard Malle Hair-relaxing composition comprising at least one base other than hydroxide
US20050186232A1 (en) * 2003-11-18 2005-08-25 Gerard Malle Hair-relaxing composition comprising tetramethylguanidine
WO2005124013A1 (en) 2004-06-10 2005-12-29 Keraplast Technologies, Ltd. New and gentle process for conversion of cystine in keratin-containing materials to lanthionine
US20060134042A1 (en) * 2003-11-18 2006-06-22 Gerard Malle Hair shaping composition comprising at least one tetramethylguanidine
AU2011203552B2 (en) * 2004-06-10 2011-10-27 Keraplast Technologies, Ltd New and gentle process for conversion of cystine in keratin-containing materials to lanthionine
EP2734185B1 (de) 2011-07-21 2019-04-10 L'oreal Verfahren zum färben von keratinfasern mit vorausgegangener dauerwellbehandlung, mittels einer einen naturfarbstoff enthaltenden zusammensetzung

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US4304244A (en) * 1977-06-09 1981-12-08 Carson Products Company Hair straightening process and hair curling process and compositions therefor
US4237910A (en) * 1979-09-24 1980-12-09 Johnson Products Co., Inc. Stable hair relaxer
US4390033A (en) * 1979-09-24 1983-06-28 Johnson Products Co., Inc. Stable hair relaxer
JPS57165362A (en) * 1981-04-03 1982-10-12 Kashiwa Kagaku Kogyo:Kk Guanidine compound and cold-wave lotion composition containing the same
US4947878A (en) * 1987-03-18 1990-08-14 Preemptive Marketing, Inc. Compositions and methods for the treatment of hair
US4898726A (en) * 1988-08-24 1990-02-06 Johnson Products Co., Inc. Initiated hair straightening composition and system
US5565216A (en) * 1993-07-21 1996-10-15 Carson Products Company Hair relaxer compositions
US5348737A (en) * 1993-07-21 1994-09-20 Avlon Industries, Inc. Composition and process for decreasing hair fiber swelling
US5533532A (en) * 1995-06-26 1996-07-09 Revlon Consumer Products Corporation Permanent wave compositions and methods
FR2751533B1 (fr) * 1996-07-23 2003-08-15 Oreal Composition de teinture d'oxydation pour fibres keratiniques comprenant un polymere amphiphile non-ionique
FR2753093B1 (fr) 1996-09-06 1998-10-16 Oreal Composition de teinture d'oxydation pour fibres keratiniques comprenant un polymere amphiphile anionique
US6723308B2 (en) 2001-11-02 2004-04-20 Kenra, Llc Hair clarifying treatment
US6805136B2 (en) * 2001-11-02 2004-10-19 Kenra, Llc Hair relaxer
FR2862212B1 (fr) * 2003-11-18 2006-05-05 Oreal Composition de defrisage des cheveux comprenant de la tetramethylguanidine
FR2862213B1 (fr) * 2003-11-18 2006-05-05 Oreal Composition de defrisage des cheveux comprenant au moins une amine secondaire ou tertiaire
FR2862211B1 (fr) * 2003-11-18 2006-05-05 Oreal Composition de defrisage des cheveux comprenant au moins une base hors hydroxyde
FR2862217B1 (fr) * 2003-11-18 2006-05-05 Oreal Composition de mise en forme des cheveux comprenant au moins une amine secondaire ou tertiaire
FR2862216B1 (fr) * 2003-11-18 2006-05-05 Oreal Composition de mise en forme des cheveux comprenant de la tetramethylguanidine
FR2862215B1 (fr) * 2003-11-18 2006-01-27 Oreal Composition de mise en forme des cheveux comprenant au moins une base hors hydroxyde
FR2878435B1 (fr) * 2004-11-26 2009-04-03 Oreal Procede de defrisage des fibres keratiniques avec un moyen de chauffage et un agent denaturant
JP2007045802A (ja) * 2005-08-12 2007-02-22 Kao Corp 縮毛矯正剤組成物
FR2919179B1 (fr) * 2007-07-24 2010-02-19 Oreal Composition capillaire comprenant au moins un colorant direct disulfure et au moins un agent alcalin hydroxyde et procede de mise en forme et de coloration simultanees.
FR2965173B1 (fr) 2010-09-24 2013-04-05 Oreal Procede de traitement des fibres keratiniques mettant en oeuvre une composition cosmetique non detergente comprenant au moins un sel de calcium
DE102013225788A1 (de) * 2013-12-12 2015-06-18 Henkel Ag & Co. Kgaa Verfahren zum Glätten, Konditionieren und Färben von Haaren, insbesondere von Haaren mit starker Krause
EP3705605A1 (de) * 2019-03-05 2020-09-09 Siemens Aktiengesellschaft Absorptionsmittel, vorrichtung und verfahren zum gewinnen von kohlenstoffdioxid und wasser aus luft

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Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4992267A (en) * 1988-04-28 1991-02-12 Johnson Products Co., Inc. Hair straightening composition and system
US7118736B2 (en) 2001-02-22 2006-10-10 L'oreal Hair relaxer compositions comprising at least one hydroxide compound and at least one activating agent, and methods of using the same
US20020159962A1 (en) * 2001-02-22 2002-10-31 Cannell David W. Hair relaxer compositions comprising at least one hydroxide compound and at least one activating agent, and methods of using the same
US20020189027A1 (en) * 2001-04-20 2002-12-19 Cannell David W. Composition and methods for lanthionizing keratin fibers using at least one organic nucleophile and at least one hydroxide ion generator
US20030037384A1 (en) * 2001-08-20 2003-02-27 Nguyen Nghi Van Compositions comprising at least one hydroxide compound and at least one oxidizing agent, and methods to straighten curly hair
WO2003015725A2 (en) * 2001-08-20 2003-02-27 L'oreal S.A. Compositions comprising at least one hydroxide compound and at least one reducing agent, and methods for relaxing hair
WO2003015725A3 (en) * 2001-08-20 2003-11-27 Oreal Compositions comprising at least one hydroxide compound and at least one reducing agent, and methods for relaxing hair
US7468180B2 (en) 2001-08-20 2008-12-23 L'oreal, S.A. Compositions comprising at least one hydroxide compound and at least one oxidizing agent, and methods to straighten curly hair
US7195755B2 (en) 2001-08-20 2007-03-27 L'oreal S.A. Compositions comprising at least one hydroxide compound and at least one reducing agent, and methods for relaxing hair
US20050125914A1 (en) * 2003-11-18 2005-06-16 Gerard Malle Hair shaping composition comprising at least one- non-hydroxide base
US20090139537A1 (en) * 2003-11-18 2009-06-04 L'oreal S.A. Hair relaxing composition comprising at least one non-hydroxide imine
US20050136016A1 (en) * 2003-11-18 2005-06-23 Gerard Malle Hair-relaxing composition comprising at least one base other than hydroxide
US20050186232A1 (en) * 2003-11-18 2005-08-25 Gerard Malle Hair-relaxing composition comprising tetramethylguanidine
US20090194124A1 (en) * 2003-11-18 2009-08-06 Gerard Malle Hair Shaping Kit and Process Comprising at Least One Non-Hydroxide Imine
US20060134042A1 (en) * 2003-11-18 2006-06-22 Gerard Malle Hair shaping composition comprising at least one tetramethylguanidine
US20050136017A1 (en) * 2003-11-18 2005-06-23 Gerard Malle Hair relaxing composition comprising at least one non-hydroxide imine
US20050136018A1 (en) * 2003-11-18 2005-06-23 Gerard Malle Hair relaxing composition comprising at least one secondary or tertiary amine
US20050136019A1 (en) * 2003-11-18 2005-06-23 Gerard Malle Hair shaping composition comprising at least one amine chosen from secondary and tertiary amines
US20050129645A1 (en) * 2003-11-18 2005-06-16 L'oreal Hair shaping composition comprising at least one non-hydroxide imine
US20080249451A1 (en) * 2004-06-10 2008-10-09 Keraplast Techologies, Ltd. Gentle Process For Conversion of Cystine in Keratin-Containing Materials to Lanthionine
WO2005124013A1 (en) 2004-06-10 2005-12-29 Keraplast Technologies, Ltd. New and gentle process for conversion of cystine in keratin-containing materials to lanthionine
AU2011203552B2 (en) * 2004-06-10 2011-10-27 Keraplast Technologies, Ltd New and gentle process for conversion of cystine in keratin-containing materials to lanthionine
US8101202B2 (en) 2004-06-10 2012-01-24 Keraplast Technologies, Ltd Gentle process for conversion of cystine in keratin-containing materials to lanthionine
EP2734185B1 (de) 2011-07-21 2019-04-10 L'oreal Verfahren zum färben von keratinfasern mit vorausgegangener dauerwellbehandlung, mittels einer einen naturfarbstoff enthaltenden zusammensetzung

Also Published As

Publication number Publication date
JPS5029756A (de) 1975-03-25
FR2220243A1 (de) 1974-10-04
FR2220243B1 (de) 1977-09-16
GB1466621A (en) 1977-03-09
GB1466622A (en) 1977-03-09
FR2220244A1 (de) 1974-10-04
IT1055551B (it) 1982-01-11
DE2410677A1 (de) 1974-09-19
US3971391A (en) 1976-07-27
NL7403048A (de) 1974-09-10
CH591859A5 (de) 1977-09-30
CA1024896A (fr) 1978-01-24
NL7403049A (de) 1974-09-10
AU6637974A (en) 1975-09-11
IT1055550B (it) 1982-01-11
AT342208B (de) 1978-03-28
CH591860A5 (de) 1977-09-30
DE2410678A1 (de) 1974-09-19
BR7401728D0 (pt) 1974-11-05
CA1041428A (fr) 1978-10-31
BE811912A (fr) 1974-09-06
ES423990A1 (es) 1977-01-01
ES423991A1 (es) 1976-05-01
AR204622A1 (es) 1976-02-20
DE2410677C2 (de) 1990-02-22
JPS5029757A (de) 1975-03-25
ATA192274A (de) 1977-07-15
AU6638074A (en) 1975-09-11
LU67178A1 (de) 1974-10-09
AT342207B (de) 1978-03-28
BE811911A (fr) 1974-09-06
ATA192374A (de) 1977-07-15
FR2220244B1 (de) 1977-09-16

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