IE53928B1 - Hair treatment process and composition - Google Patents

Hair treatment process and composition

Info

Publication number
IE53928B1
IE53928B1 IE238/83A IE23883A IE53928B1 IE 53928 B1 IE53928 B1 IE 53928B1 IE 238/83 A IE238/83 A IE 238/83A IE 23883 A IE23883 A IE 23883A IE 53928 B1 IE53928 B1 IE 53928B1
Authority
IE
Ireland
Prior art keywords
hair
waving
weight
lotion
neutralizing
Prior art date
Application number
IE238/83A
Other versions
IE830238L (en
Original Assignee
Bristol Myers Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=23360566&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=IE53928(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Bristol Myers Co filed Critical Bristol Myers Co
Publication of IE830238L publication Critical patent/IE830238L/en
Publication of IE53928B1 publication Critical patent/IE53928B1/en

Links

Classifications

    • 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
    • A61K8/22Peroxides; Oxygen; Ozone
    • 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
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8158Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
    • 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
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • 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
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54Polymers characterized by specific structures/properties
    • A61K2800/542Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5426Polymers characterized by specific structures/properties characterized by the charge cationic

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Cosmetics (AREA)

Abstract

A process for waving or straightening hair that leaves the hair in conditioned form which comprises treating the hair with a novel hair waving composition containing a reducing agent and certain cationic polymers followed by treating said hair with a "neutralizing" composition containing an oxidizing agent and an anionic or amphoteric detergent.

Description

This invention relates to compositions for waving or straightening hair, and especially human hair, and to processes for effecting the same. More particularly, it concerns compositions and methods of the aforesaid character which leaves the hair in a conditioned or improved manner.
Hair waving or straightening (also often referred to as “permanent treatment) usually involves the application of an agent for reducing or cleaving the disulfide linkages of keratin in hair (hereinafter referred to as reducing agent, and compositions containing a reducing agent hereinafter referred to as reducing or “waving composition or “lotion), thereby to permit hair to be shaped without any internal elasticity or other resistance, and the subsequent application of a neutralizing agent which reestablishes the keratin linkages and sets the hair in its new, desired shape. The neutralizing agent is generally an oxidizing solution, such as an aqueous solution of hydrogen peroxide and the like.
Distinguished from the waving and straightening of hair by a reducing lotion, is the so-called relaxing of hair wherein a strong alkali, usually in the form of a paste or cream is employed. The mechanism of the action of the alkali is different from the mechanism of action of the reducing agent in conventional permanent waving and straightening. While in the latter case the disulfide linkages of keratin are cleaved and remain cleaved until restored by the neutralizer, in the caustic alkaline treatment the disulfide linkages of keratin are converted to monosulfide bonds and the following neutralization with an acid is merely the conventional neutralization of the residual base with an acid. Hence the terms waving and “straightening'1, as used herein, do not contemplate the relaxation of hair by strong bases.
Having or straightening of hair with reducing agents such as mercaptans, sulfites or phospines is almost invariably accompanied by deterioration of tactile properties of hair, increased tangling and difficult combing. This is true for all types of hair and particularly bothersome for hair which, prior to waving, had been exposed to bleaching, coloring or prolonged weathering. The conventional way to ameliorate this situation is to treat the waved hair with conditioning agents such as alkyl-dimethyl benzyl halides, emulsions of mineral oil, lanolin, etc. Conditioning agents of this type are usually incorporated in the neutralizing step of the waving or the straightening process, Nhile these conditioning compounds improve the feel of hair and allow for easier comoing, their beneficial effects are only tran10 sitory and are entirely lost when the hair is shampooed.
U.S. patent No. 3,912,808 to Sokol discloses a process for waving or straightening hair which involves a waving lotion containing a reducing agent and a polydiroethyldiallylammonium chloride, a cationic polymer. The teaching of this patent is employed in a commercial product which was tested and compared in connnection with this application. Polydimethyldiallylammonium chloride is not being used in accordance with the present invention.
U.S. patent No. 4,175,572 to Hsiung et al. relates to a caustic alkaline hair relaxer and not to waving or straightening, which, among others, also contains polydimethyldiallylammonium chloride. The polymer can be applied also separately from the alkaline relaxer, before or after its application. It is stated that an acidic shampoo is employed after relaxing and conditioning to remove the excess alkaline solution. The last shampoo step or its composition is not specified further and it is stated not to be a part of the conditioning process. In that sense it can be equated to the commercial product based on the above-mentioned U.S. patent No. 3,912,808 in which a cationic surfactant is employed in the neutralizing composition. In contrast, in addition to not employing polydimethyldiallylammonium chloride, the present invention requires the presence specifically of an anionic surfactant to form the conditioning precipitate in the presence of hair. Furthermore, the present invention is not useful in connection with strong alkali relaxer compositions.
It has now been found that durable conditioning of hair can be obtained in a hair waving or a hair straightening process that is superior in its effects to conventional techniques and persists through repeated shampooing which comprises treating said hair with an aqueous waving carposition containing an effective amount of reducing agent and at least one cationic polymer as defined below, and then treating said hair with an aqueous neutralizing composition containing an oxidizing agent and an anionic surfactant.
As a result of the sequence of the initial reducing in the waving (or straightening) and subsequent neutralizing steps and a unique combination of ingredients, a conditioning complex, stable to repeated snampooings, is formed in the hair.
It is accordingly an object of this invention to provide a pro10 cess for waving or straightening hair which leaves the hair in a conditioned fashion which resists repeated shampooings.
It is also an object of the present invention to provide compositions which are useful in carrying out the aforesaid process.
Other and more detailed objects of this invention will be appar15 ent from the following description and claims.
In the following description and the claims, wherever possible, reference is made to chemicals by their CTFA names as contained in the Cosmetic Ingredient Dictionary of The Cosmetic, Toiletry and Fragrance Association, Inc.
Molecular weights are given on a weight average basis.
The at least one cationic polymer employed in accordance with . the present invention comprises a polymer of methacrylamidopropyltrimethylammonium chloride. This has been found to give excellent results. It is obtainable by polymerizing in a manner known per se the corresponding monaner. The mananer is sold by Texaco Chemicals under the name MAPTAC. The polymer specified is said to be constituted of repeating where n is a number which is proportional to molecular weight. The molecular weight is advantageously between 5,000 and 500,000. This polymer is hereafter referred to as Clairquat-1.
As mentioned above, the particular Cationic polymers described are contained in the reducing lotion employed in the process. The quantity of cationic polymer that will be present in the reducing lotion can vary somewhat depending on the results that are desired. Ordinarily, this will constitute between 0.2% to 10% by weight based on the total weight of the reducing lotion with the optimal range being between about 1% to 5% by weight thereof.
No structural or known physico-chemical features of cationic polymers can be used to predict whether a cationic polymer can be used in accordance with the present invention. Accordingly it was found that a number of cationic polymers, when suostituted for those disclosed and claimed herein, will produce inadequate durable conditioning of hair. Some of these cationic polymers that were found to work insufficiently, are: quaternized poly-2-vinylpyridine adipic acid/epoxypropyl diethylenetriamine copolymer (sold by Hercules Chemical Co. under the name Delsette 101); adipic acid/dimethylaminohydroxypropyldiethylenetriamine copolymer (sold by Sandoz, Inc. under the name Cartaretic F-4); poly (N-(3-dimethylamino)propyl)-N'-(3-(ethyleneoxyethylene dimethylamino)propyl) urea dichloride (sold under the name Mirapol A15 by Miranol Chemical Co., Inc.); quaternium-23, a quaternary ammonium polymer formed by the reaction of dimethyl sulfate and a copolymer of vinyl pyrrolidone and dimethylaminoethylmethacrylate (sold by GAF Corporation under the name Gafquat*755N); quaternium-19, a polymer of hydroxyethyl cellulose reacted with epichlorohydrin and then quaternized with trimethyl amine (sold by Union Carbide Corp, under the name Polymer JR-400); a quaternary ammonium derivative of a hydrolyzed collagen protein (sold by Croda, Inc. under the name of Crotein Q); quaternium-39, a copolymer of acrylamide and beta-methacryloxyethyl trimethyl ammonium methosulfate (sold by Hercules Chemical Co. under the name Reten*205 M); * Gafquat and Reten are Trade Marks. 33928 aminoethyl acrylate phosphate/acrylate copolymer (sold by National Starch Co. under the name Catrex); and quaternium-41 which is a copolymer of dimethyldiallylammonium chloride with acrylamide (sold by Merck & Co., Inc. under the name 5 Merquat-550). in addition to the cationic polymer, the waving or reducing lotion employed in this invention can also contain other conventional ingredients commonly employed in such waving lotion. Thus, the vehicle for the lotion is an aqueous vehicle which has incorporated therein one or more reducing agents. A variety of reducing agents are known in the prior art which are useful in waving or straightening hair. By way of example, we can mention thioglycollic acid, cysteine, thiolactic acid, sodium-, potassium-, and ammonium sulfites and bisulfites, tris(hydroxyethyl phosphine). Although the present invention can be employed with all waving and straightening compositions, in the preferred form of this invention the reducing agents that will be employed are thioglycollic acid and alkali metal salts e.g. sodium salts of sulfurous acids (e.g. sulfites and bisulfites) .
The quantity of reducing agent contained in the waving lotion will also vary somewhat depending on the agent selected and the results desired. Usually, however, the waving lotion will contain from 0.5% to 20% by weight of reducing agent based on the total weight of the waving lotion. Optimal results are obtained when the reducing agent coinprises from about 2% to 10% by weight based on the total weight of the lotion. The term effective amount, as used throughout the specification and the claims with respect to any ingredient of the composition, means an amount effective to achieve the intended purpose. Generally there is no criticality in any given range of concentration and the invention does not reside in any particular concentration, but rather in the components themselves. The amount that is most effective can be determined by routine experimentation.
In addition, the waving lotion can also contain fragrances, alkalizing agents and other conventional waving lotion ingredients. Most often the lotion has a pH in the range of from about 5 to 10. 53828 The second essential component of the present conditioning system are amphoteric or anionic detergents which will constitute part of the neutralizing lotion. There are a number of amphoteric detergents that are suitable For use in the present invention. However, two classes of detergents have been found to be especially effective. The first class can be defined by the formula: CH,C00Na L C -N-CH2CH2OCH2COO CH in which R is a long chain fatty radical containing from 10 to 18 carbon atoms. A typical example of such a compound or compounds is the case in which R represents coconut fatty radicals. A material of this character is known as amphoteric-2 and is sold under the trade name Miranol C2MSF.
A second variety of amphoteric detergents that is particularly effective for the purposes of the present invention can be defined by the formula: R — NH-CHj-CH2-COOH wherein R is a long chain fatty alkyl group having from 10 to 18 carbon atoms. In an example of such a detergent the R in the formula is a mixture of lauryl and myristyl fatty alkyl groups. This material is known as lauraminopropionic acid and is sold under the trade name Deriphat 170C.
Not all amphoteric surfactants were found to be suitable. None of a number of betaines worked in accordance with the present invention. Since betaines are zwitterionic compounds, it could be expected that some zwitterionic surfactants may not work as well, although we found zwitterionic surfactants that are acceptable. As used throughout the specification and the claims, the term ampho53928 teric surfactant product denotes that the amphoteric surfactant will work in accordance with the invention. Whether any amphoteric surfactant is an amphoteric surfactant product can be simply and routinely determined by adding an aqueous solution of the surfactant to an alkaline pH solution of one of the claimed cationic polymers and if a precipitate is formed, then the amphoteric surfactant is an ampohteric surfactant product. Since amphoteric surfactants become anionic above their pKa value, the term anionic surfactant as used throughout the specification and the claims, encompasses both anionic surfactants and amphoteric surfactant products.
All anionic detergents that were tested have been found useful in this invention; thus, salts of alkyl sulfonates, alkyl sulfates, sulfonated and sulfated alkyl ethers as well as long chain carDoxylic acids (where the chain length is at least c10) exhibit forma15 tion of conditioning complexes. By way of specifically illustrating the anionic detergents that are useful herein, the following may be mentioned: sodium lauryl sulfate, sodium lauryl ether sulfate, TEA lauryl sulfate and sodium stearate.
The quantity of amphoteric or anionic detergent which will be contained in the neutralizing lotion of this invention will vary somewhat again depending on the economics and the results sought.
However, usually this will be in the range of from about 0.2 to 50% by weight and ideally, in the range of from about 0.5% to 20% by weight based on the total weight of the neutralizing lotion.
The neutralizing lotion can also contain other ingredients usually employed in such neutralizing lotions that are utilized in hair waving or hair straightening procedures. Again, the vehicle will ordinarily be an aqueous vehicle which will contain an oxidiz30 ing agent that will serve to neutralize the action of the reducing agent contained in the waving lotion after the latter has been applied to the head. A number of oxidizing agents are known to those skilled in this art which will accomplish this purpose. These include, e.g., hydrogen peroxide, sodium-and potassium bromates and sodium perborate.
The quantity of oxidizing agent that will be contained in the neutralizing lotion can also vary somewhat; again, depending on the agent selected and the results desired. For the most part, this will comprise between 0.2% to 20% by weight of the neutralizing lotion based on the total weight of said neutralizing lotion. In a preferred form of the invention, the oxidizing agent will constitute about IS. to 10% by weight based on the total weight of the neutralizing lotion.
In addition to the above, among the other ingredients that can be contained in the neutralizing lotion. Mention can be made of such materials as organic and inorganic acids (e.g. phosphoric and citric acid). The pH of the neutralizing lotion will usually be in the range of from about 2 to 10, except when an amphoteric surfactant is employed in which case the pH would be more on the basic side.
The term anionic surfactant, as used throughout the specification and the claims, includes amphoteric surfactant products when the pH of the neutralizing composition is above the pKa value of the amphoteric surfactant product, since at such basic pH levels the amphoteric has anionic character.
Conveniently the compositions of the present invention can be sold in a package containing two containers, one containing the waving lotion including the cationic polymer and the reducing agent, and the other containing the reducing solution which contains the reducing agent and the anionic surfactant.
The following specific example is intended to illustrate more fully the nature of the present invention without limiting its scope.
EXAMPLE Waving Lotion - A hair waving lotion was prepared having the following composition: £3328 By Wt. ammonium thioglycol late 7.0 monoethanolamine 3.5 fragrance 0.1 Clairquat-1 3-0 water to 100.0 Neutralizing Lotion - This was prepared having the following composition: By Wt. amonium lauryl sulfate 3.0 hydrogen peroxide 1.4 phosphoric acid 0.1 water to 100.0 In addition to the above samples, both the waving lotion and the neutralizer have also been prepared without the cationic polymer and the anionic detergent respectively.
Four sets of intact Caucasian hair tresses were treated under identical conditions of time and temperature followed by rinsing and neutralization. The tresses were wound on 1/2 inch rods and two of them saturated with the waving lotion containing the polymer while the other two were saturated with the waving lotion without that cationic polymer. All tresses were then wrapped in Saran Wrap and placed for 20 minutes in an over kept at 35°C. After this time, the waving lotion was rinsed off and the tresses, while still on rods, were treated for 5 minutes with the neutralizing solutions. The neutralizing solution containing ammonium lauryl sulfate was applied to two waved tresses (one waved with and one without the polymer) while the other two were exposed to the neutralizer in which there was no ammonium lauryl sulfate present. it was found that only in the case of the waved hair tress where the waving solution employed contained the polymer and where the neutralizer contained the anionic detergent, was it soft, lustrous and conditioned. The effect was found to be durable by being resistant to at least four shampoos.
Although the inventicn has been described with reference to specific forms thereof, it will be understood that many changes and modifications msy be made without departing frcm the anbit of this invention, as defined in the claims which, follow.

Claims (7)

1. CLAIMS;
1. A process for waving or straightening hair which leaves the hair in a conditioned form which conditioning persists through repeated shampooing, which comprises: (a) treating said hair with an aqueous waving composition containing an effective amount of reducing agent and at least one cationic polymer comprising a polymer of methacrylamidopropyl-trimethylammonium chloride, and then, (b) treating said hair with an aqueous neutralizing composition containing an oxidizing agent and an anionic surfactant.
2. A process according to claim 1 in which the waving composition contains, based on the weight of said waving composition, from 0.5% to 20% by weight of said reducing agent and from 0.2% to 10% by weight of said cationic polymer, and said neutralizing composition contains, based on the weight of said neutralizing composition, from 0.2% to 20% by weight of oxidizing agent and from 0.2% to 50% by weight of said surfactant.
3. A process according to claim 1 or 2 in which: (a) said reducing agent is thioglycollic acid or an alkali metal salt of sulfurous acid; (b) said cationic polymer has a molecular weight between 5,000 and 500,000; (c) said oxidizing agent is hydrogen peroxide or sodium or potassium bromate; and (d) said detergent is sodium or ammonium lauryl sulfate.
4. An aqueous hair waving composition useful in the waving or straightening of hair containing, based on the weight of the waving composition: (a) from 0.5% to 20% by weight of a reducing agent.; and (b) from 0.2% to 10% by weight of at least one cationic polymer comprising a polymer of methacrylamidopropyltrimethylammonium.
5. A two part package for use in waving or straightening 5 of hair, said package containing two containers, one of said containers comprising waving lotion which is an aqueous solution of a reducing agent, and at least one cationic polymer comprising a polymer of methacrylamidopropyl-trimethylammonium, and the other container comprising 10 a neutralizing lotion which is an aqueous solution of an oxidizing agent and an anionic surfactant.
6. A process according to claim 1, substantially as described in the foregoing Example.
7. A two part package according to claim 5, substantially 15 as described in the foregoing Example.
IE238/83A 1982-02-08 1983-02-07 Hair treatment process and composition IE53928B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US34668482A 1982-02-08 1982-02-08

Publications (2)

Publication Number Publication Date
IE830238L IE830238L (en) 1983-08-08
IE53928B1 true IE53928B1 (en) 1989-04-12

Family

ID=23360566

Family Applications (1)

Application Number Title Priority Date Filing Date
IE238/83A IE53928B1 (en) 1982-02-08 1983-02-07 Hair treatment process and composition

Country Status (18)

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JP (1) JPS58150506A (en)
BE (1) BE895854A (en)
BR (1) BR8300583A (en)
CA (1) CA1190857A (en)
CH (1) CH660114A5 (en)
DE (1) DE3303346A1 (en)
DK (1) DK51883A (en)
ES (1) ES8501971A1 (en)
FR (1) FR2521004B1 (en)
GB (1) GB2114616B (en)
GR (1) GR77409B (en)
IE (1) IE53928B1 (en)
IT (1) IT1203648B (en)
MX (1) MX158289A (en)
NL (1) NL8300412A (en)
NZ (1) NZ203095A (en)
SE (1) SE461436B (en)
ZA (1) ZA83863B (en)

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AU578780B2 (en) * 1985-02-04 1988-11-03 Chesebrough-Pond's Inc. Hair waving and straightening compositions of matter
CA1266829A (en) * 1985-02-07 1990-03-20 Du Yung Hsiung Permanent wave neutralizer composition and method
US4656043A (en) * 1985-09-13 1987-04-07 Richardson-Vicks Inc. Peroxide-containing conditioning shampoo
JP2568083B2 (en) * 1987-05-18 1996-12-25 政夫 齋藤 Permanent method
WO1989007435A2 (en) * 1988-02-19 1989-08-24 Amethyst Investment Group, Inc. Permanent wave process and compositions
US4996997A (en) * 1988-02-19 1991-03-05 Amethyst Investment Group, Inc. Permanent waving process and compositions
FR2657254B1 (en) * 1990-01-19 1992-04-10 Oreal REDUCING COSMETIC COMPOSITION FOR PERMANENT HAIR, BASED ON N-ACETYLCYSTEAMINE AND A CATIONIC POLYMER, AND ITS USE IN A PERMANENT HAIR DEFORMATION PROCESS.
FR2655541B1 (en) * 1989-12-08 1992-02-21 Oreal REDUCING COSMETIC COMPOSITION FOR PERMANENT HAIR, BASED ON CYSTEAMINE AND A CATIONIC POLYMER, AND USE THEREOF IN A PROCESS OF PERMANENT DEFORMATION OF HAIR.
CA2031833A1 (en) * 1989-12-08 1991-06-09 Claude Dubief Cosmetic composition to reduce hair perm, made with cysteamin or its n-acetyl derivative and a cationic polymer, and its use in a process for permanently uncurling hair
US5415856A (en) * 1990-05-08 1995-05-16 Preemptive Advertising Inc. Hair treatment compositions containing disaccharides
JP2516284B2 (en) * 1991-04-04 1996-07-24 花王株式会社 Two-component hair treatment composition and hair treatment method
FR2675379A1 (en) * 1991-04-16 1992-10-23 Oreal Hair-care composition for shaping the hair and corresponding hair-shaping process
JP2523418B2 (en) * 1991-08-13 1996-08-07 花王株式会社 Two-agent keratinous fiber treating agent composition
GB2312444A (en) * 1996-04-27 1997-10-29 R & C Products Pty Ltd Keratin fibre modification using quaternary ammonium compounds
US6125856A (en) * 1999-04-21 2000-10-03 Phild Co., Ltd. Hair repair, styling, and straightening process
US6805136B2 (en) 2001-11-02 2004-10-19 Kenra, Llc Hair relaxer
US6723308B2 (en) 2001-11-02 2004-04-20 Kenra, Llc Hair clarifying treatment
DE10338883A1 (en) * 2003-08-23 2005-03-24 Hans Schwarzkopf & Henkel Gmbh & Co. Kg Process for smoothing keratin-containing fibers
FR2997848B1 (en) * 2012-11-09 2015-01-16 Oreal COMPOSITION COMPRISING A DICARBONYL DERIVATIVE AND A METHOD FOR SMOOTHING THE HAIR THEREFROM
EP4119122A1 (en) * 2021-07-13 2023-01-18 Kao Germany GmbH Process for permanent waving keratin fibers

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US2980657A (en) * 1954-07-06 1961-04-18 Rohm & Haas Quaternary ammonium compounds of polymers of acrylamido type and methods for making them
FR2010319A1 (en) * 1968-06-07 1970-02-13 Roehm & Haas Gmbh
US3912808A (en) * 1970-02-25 1975-10-14 Gillette Co Hair waving and straightening process and composition containing water-soluble amino and quaternary ammonium polymers
US3986825A (en) * 1972-06-29 1976-10-19 The Gillette Company Hair coloring composition containing water-soluble amino and quaternary ammonium polymers
US4027008A (en) * 1975-05-14 1977-05-31 The Gillette Company Hair bleaching composition containing water-soluble amino and quaternary ammonium polymers
JPS5261237A (en) * 1975-11-13 1977-05-20 Oreal New cosmetic compound on basis of quaternarized polymer
LU76955A1 (en) * 1977-03-15 1978-10-18
FR2472382A1 (en) * 1979-12-28 1981-07-03 Oreal Hair perming by redn. and oxidn. - in presence of cationic polymer and anionic surfactant
US4366827A (en) * 1979-12-28 1983-01-04 Societe Anonyme Dite: L'oreal Procedure for the permanent reshaping of hair, and composition intended for carrying out said procedure
CA1138341A (en) * 1980-01-23 1982-12-28 Leszek J. Wolfram Waving composition from a reducing agent and cationic polymer

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Publication number Publication date
NL8300412A (en) 1983-09-01
ZA83863B (en) 1983-11-30
BE895854A (en) 1983-08-08
SE461436B (en) 1990-02-19
DK51883D0 (en) 1983-02-08
JPH0425251B2 (en) 1992-04-30
IE830238L (en) 1983-08-08
AU1091683A (en) 1983-08-18
DK51883A (en) 1983-08-09
BR8300583A (en) 1983-11-08
AU547971B2 (en) 1985-11-14
CA1190857A (en) 1985-07-23
CH660114A5 (en) 1987-03-31
SE8300626L (en) 1983-08-09
ES519303A0 (en) 1984-12-16
GB2114616A (en) 1983-08-24
IT1203648B (en) 1989-02-15
JPS58150506A (en) 1983-09-07
DE3303346A1 (en) 1983-10-13
GR77409B (en) 1984-09-13
FR2521004A1 (en) 1983-08-12
SE8300626D0 (en) 1983-02-07
GB8303349D0 (en) 1983-03-09
NZ203095A (en) 1986-10-08
MX158289A (en) 1989-01-20
GB2114616B (en) 1985-12-18
FR2521004B1 (en) 1987-01-23
IT8347676A0 (en) 1983-02-07
ES8501971A1 (en) 1984-12-16

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