WO1997041828A1 - Mittel und verfahren zur dauerhaften haarverformung auf basis von mercaptoacetamiden sowie verfahren zu deren herstellung - Google Patents
Mittel und verfahren zur dauerhaften haarverformung auf basis von mercaptoacetamiden sowie verfahren zu deren herstellung Download PDFInfo
- Publication number
- WO1997041828A1 WO1997041828A1 PCT/EP1997/001028 EP9701028W WO9741828A1 WO 1997041828 A1 WO1997041828 A1 WO 1997041828A1 EP 9701028 W EP9701028 W EP 9701028W WO 9741828 A1 WO9741828 A1 WO 9741828A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- agent
- hair
- shaping
- water
- mercaptoacetamides
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/04—Preparations for permanent waving or straightening the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
Definitions
- the present invention relates to an agent for permanent hair shaping, which as a keratin-reducing active ingredient is a mercaptoacetamide of the formula
- the classic technique for performing permanent hair shaping is based on two treatment steps.
- the cystine-disulfide bridges of hair keratin are opened by the action of an agent which contains a reducing active ingredient (shaping agent). Then the hair is brought into the desired shape.
- cystine-disulfide bonds are made using a fixative, i.e. of an agent containing an oxidizing agent, closed again
- thioglycolic acid for example as an ammonium or monoethanolamine salt
- Other common reducing agents are inorganic sulfites, 2-mercapto-propionic acid (thiolactic acid), 3-mercapto-propionic acid, certain mercaptocarboxylic acid esters, cysteine and derivatives of these compounds.
- thiolactic acid 2-mercapto-propionic acid
- 3-mercapto-propionic acid 2-mercapto-propionic acid
- certain mercaptocarboxylic acid esters certain mercaptocarboxylic acid esters
- cysteine and derivatives of these compounds are all of these means have a number of disadvantages.
- Alkaline preparations based on the mercaptocarboxylic acids show hair damage despite sufficient action, which manifests itself, for example, in increased hair breakage. In many cases, these agents also have an undesirable impact on the scalp.
- thiolactic acid 2-mercapto-propionic acid
- the mercaptocarboxylic acid esters which allow hair shaping even at lower pH values, are unsatisfactory in terms of their skin tolerance and their risk of sensitization.
- mercaptocarboxylic acid amides such as thioglycolic acid amide or alkyl- or hydroxyalkyl-substituted mercaptocarboxylic acid amides were also used.
- these substances have a high forming potential even at low pH values, but are even more critical than the mercaptocarboxylic acid esters in terms of sensitization.
- the present invention therefore relates to an agent for permanent shaping of the hair, which is characterized in that it is a compound of the general formula as a keratin-reducing active ingredient
- the mercaptoacetamides contained in the agents according to the invention are used in the ready-to-use agent for permanent hair shaping preferably in an amount of 3 to 28 percent by weight, particularly preferably in an amount of 5 to 21 percent by weight
- the mercaptoacetamides can also be used in a mixture with other known thiols, such as thioglycolic acid, thiolactic acid, cysteine, cysteamine, alkyl- or acylcysteamines or sulfites
- the ready-to-use hair styling agents preferably have a pH of 6.5 to 9.5, particularly preferably 6.5 to 8.5.
- Ammonia or sodium hydroxide solution in particular, but also all other water-soluble, physiologically acceptable salts of organic and inorganic bases, such as, for example, come as alkali agents or as agents for adjusting the pH.
- the shaping agent can be made up as a one-, two- or three-component preparation, it being possible for the agent to be present both in the form of an aqueous solution or an emulsion and in thickened form on an aqueous basis, in particular as a cream, gel or paste.
- the agent according to the invention can be obtained by mixing two components, of which the first component contains at least one alkalizing agent, for example an alkali carbonate, ammonium carbonate, alkali hydrogen carbonate or ammonium hydrogen carbonate, and a mercaptoacetamide of the formula (I) and the second component contains at least one of the following contains cosmetic additives and water.
- the first component contains at least one alkalizing agent, for example an alkali carbonate, ammonium carbonate, alkali hydrogen carbonate or ammonium hydrogen carbonate, and a mercaptoacetamide of the formula (I)
- the second component contains at least one of the following contains cosmetic additives and water.
- the agent according to the invention in the form of a three-component preparation, one component containing some of the cosmetic additives mentioned below and water, a second, anhydrous component containing a mercaptoacetamide of the formula (I) and the third component further additives, such as e.g. B. contains perfume oils, solubilizers and care substances, in aqueous solution or in anhydrous form.
- the cosmetic additives can be contained both in the aqueous and in the non-aqueous component (s).
- the shaping agent can contain all additives which are customary and known for such agents, for example thickeners, such as, for example, bentonite, fatty acids, starch, polyacrylic acid and derivatives thereof, cellulose derivatives, alginates, petroleum jelly, paraffin oils; Wetting agents or emulsifiers from the classes of anionic, cationic, amphoteric or nonionic surface-active substances, for example fatty alcohol sulfates, fatty alcohol ether sulfates, alkyl sulfonates, alkylbenzenesulfates, quaternary ammonium salts, alkylbetaines, oxyethylated alkylphenols, fatty acid alkanolamides or oxyethylated fatty acids; opacifiers, such as polyethylene glycol esters; Alcohols such as ethanol, propanol, isopropanol and glycerin; Sugar such as B. D-glucose; Solubilizers,
- constituents mentioned are used in the amounts customary for such purposes, for example the wetting agents and emulsifiers in concentrations of
- REPLACEMENT SHEET (RULE 25) a total of 0.2 to 30 percent by weight, the alcohols in a total amount of 0.1 to 20 percent by weight, the opacifiers, perfumes and dyes in an amount of 0.01 to 1 percent by weight each, the buffer substances in a total amount of 0.1 up to 10 percent by weight, sugar, solubilizers, stabilizers, and hair conditioning and hair care ingredients in an amount of 0.1 to 5 percent by weight, while the thickeners and solubilizers can be contained in a total amount of 0.5 to 20 percent by weight.
- So-called swelling and penetration substances such as, for example, dipropylene glycol monomethyl ether, 2-pyrrolidone or imidazolide-2-one, can also be added to this agent to increase the activity, in an amount of 1 to 30 percent by weight and to avoid over-curling of the hair, dithio compounds, for example dithiodiglycolic acid, dithiomilchoic acid Dithiols of the compounds mentioned or the respective salts can be added.
- an agent can be made available that is universally suitable for any hair structure, possibly with additional heat.
- the agent causes an elastic, permanent and even shaping from the hairline to the tip of the hair without causing allergic or sensitizing reactions.
- the present invention further relates to a method for permanent hair shaping, in which the hair is treated with a shaping agent before and / or after it is brought into the desired shape, is rinsed with water, then treated oxidatively, rinsed with water, and if necessary placed in a water wave and then drying, which is characterized in that the agents according to the invention described above are used as the shaping agent.
- the hair is first washed with a shampoo and then rinsed with water.
- the towel-dried hair is then divided into individual strands and wound on curlers with a diameter of 5 to 30 millimeters, preferably 5 to 15 millimeters.
- the hair is then treated with a sufficient amount, preferably 60 to 120 grams, of the shaping agent according to the invention described for hair shaping.
- the hair is rinsed with water and then oxidatively treated ("fixed").
- the post-treatment agent is used, depending on the hair, preferably in an amount of 80 to 100 grams
- Any post-treatment agent suitable for such a treatment can be used for the oxidative after-treatment in the wound or unwound state.
- oxidizing agents which can be used in such aftertreatment agents are potassium and sodium bromate, sodium perborate, urea peroxide and hydrogen peroxide.
- the concentration of the oxidizing agent varies depending on the application time (usually 5 to 15 minutes) and the application temperature.
- the oxidizing agent is normally present in the ready-to-use aqueous aftertreatment agent in a concentration of 0.5 to 10 percent by weight.
- the agent for the oxidative aftertreatment can of course contain other substances, such as wetting agents, care substances such as cationic polymers, weak acids, buffer substances or peroxide stabilizers, and in the form of an aqueous solution, an emulsion and in thickened form on an aqueous basis, in particular as a cream, Gel or paste, present
- these customary additives can be present in the aftertreatment agent in particular in an amount of 0.1 to 10% by weight
- the solvent is distilled off in vacuo on a circulation evaporator, the residue is brought to pH 7.0 by adding sodium hydroxide solution and extracted again with ethyl acetate. The combined fractions are dried over sodium sulfate and concentrated. The residue is distilled using a short path distillation apparatus at a maximum of 0.01 Torr to the pure product. This procedure is of crucial importance for achieving a product that is as pure as possible in good yield. Contamination from incompletely reacted educts and decomposition products from thermolysis or hydrolysis can only be avoided by careful distillation because of their sensitizing properties.
- glycerol monothioglycolate as a reference substance
- 1 6.5 centimeters long, pre-bleached and therefore damaged hair strands (consisting of approx. 100 hairs) from Central European hair were wound onto standardized spiral winders (inside diameter: 3 millimeters) and after conditioning in Klimara (temperature: 20 ° C; Humidity: 65%) treated with a solution of the reducing agents containing 87 mmol / 100 g and adjusted to the respective pH.
- the amount of corrugated liquid applied was calculated using the ratio 1: 1, 2 (1 g of hair: 1, 2 ml of corrugated liquid). 20 minutes were chosen as the exposure time; the exposure temperature was 50 degrees Celsius. The
- the wave stability (WSN) is calculated according to the following formula:
- Table I shows that the waving efficiencies of the mercaptoacetamides according to the invention are higher at pH 7, 8 and 9 than with thiolactic acid.
- the pH of this agent is in the range of 7.0 to 7.5.
- Hair damaged beforehand by color treatments is washed with a shampoo, terry toweling and wound on curlers with a diameter of 8 millimeters. Then the hair styling agent described above is evenly distributed on the wound hair.
- the hair is then covered with a plastic hood and heated under a drying hood at a temperature of 45 degrees Celsius for 10 minutes. The cover is then removed, the hair is rinsed with water and oxidatively aftertreated with 100 grams of a 3 percent aqueous hydrogen peroxide solution. After removing the curlers, the hair is rinsed again with water, placed in a water wave and then dried.
- the pH range of this agent is 8.0 to 8.5
- the hair treated in this way has an even and lively frizzy.
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP97906147A EP0840592A1 (de) | 1996-05-08 | 1997-03-01 | Mittel und verfahren zur dauerhaften haarverformung auf basis von mercaptoacetamiden sowie verfahren zu deren herstellung |
JP9539457A JPH11509556A (ja) | 1996-05-08 | 1997-03-01 | メルカプトアセトアミド類を主薬とするパーマネントヘア加工用の薬剤及び方法、並びにその製造方法 |
BR9702246A BR9702246A (pt) | 1996-05-08 | 1997-03-01 | Agentes e processos para a moldagem dos cabelos permanente á base de mercaptoacetamidas bem como processos para a sua preparação |
US08/981,367 US6153178A (en) | 1996-05-08 | 1997-03-01 | Agent and process for permanent hair wave based on mercaptoacetamides |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19618445A DE19618445A1 (de) | 1996-05-08 | 1996-05-08 | Mittel und Verfahren zur dauerhaften Haarverformung auf Basis von Mercaptoacetamiden sowie Verfahren zu deren Herstellung |
DE19618445.2 | 1996-05-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1997041828A1 true WO1997041828A1 (de) | 1997-11-13 |
Family
ID=7793675
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1997/001028 WO1997041828A1 (de) | 1996-05-08 | 1997-03-01 | Mittel und verfahren zur dauerhaften haarverformung auf basis von mercaptoacetamiden sowie verfahren zu deren herstellung |
Country Status (8)
Country | Link |
---|---|
US (1) | US6153178A (de) |
EP (1) | EP0840592A1 (de) |
JP (1) | JPH11509556A (de) |
AR (1) | AR006612A1 (de) |
BR (1) | BR9702246A (de) |
DE (1) | DE19618445A1 (de) |
ES (1) | ES2114849T1 (de) |
WO (1) | WO1997041828A1 (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1639992A2 (de) * | 1997-01-11 | 2006-03-29 | Wella Aktiengesellschaft | Verfahren zur Herstellung von N-verzweigtkettig alkylsubstituierten Mercaptoacetamiden |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19732079C1 (de) * | 1997-07-25 | 1999-02-04 | Wella Ag | Gesättigte, alkylsubstituierte N-Mercaptoacetyl-Heterocyclen, Mittel und Verfahren zur dauerhaften Haarverformung auf deren Basis |
US6264932B1 (en) * | 1997-07-31 | 2001-07-24 | Wella Aktiengesellschaft | Agent and method for permanent shaping of hair and method for the production of N-alkylmercaptoacetamides |
DE19733952C2 (de) * | 1997-08-06 | 1999-12-23 | Wella Ag | Mittel zur dauerhaften Haarverformung auf Basis von N,N-disubstituierten Mercaptoacetamiden sowie Verfahren zur Herstellung dieser Mercaptoacetamide |
DE10016406A1 (de) * | 2000-04-01 | 2001-10-25 | Wella Ag | Mittel und Verfahren zur dauerhaften Haarverformung auf Basis von 2-Mercaptopropionsäureamiden sowie Verfahren zu deren Herstellung |
EP1880708A1 (de) * | 2006-07-21 | 2008-01-23 | Wella Aktiengesellschaft | Verfahren und Zusammensetzung zur dauerhaften Haarverformung |
EP1880706A1 (de) * | 2006-07-21 | 2008-01-23 | Wella Aktiengesellschaft | Verfahren und Zusammensetzung zur dauerhaften Haarverformung |
EP1880707A1 (de) * | 2006-07-21 | 2008-01-23 | Wella Aktiengesellschaft | Verfahren und Zusammensetzung zumr dauerhaften Haarverformung |
EP1880710A1 (de) * | 2006-07-21 | 2008-01-23 | Wella Aktiengesellschaft | Verfahren und Zusammensetzung zumr dauerhaften Haarverformung |
EP1880709A1 (de) * | 2006-07-21 | 2008-01-23 | Wella Aktiengesellschaft | Verfahren und Zusammensetzung zur dauerhaften Haarverformung |
JP5276174B2 (ja) * | 2008-08-25 | 2013-08-28 | ザ プロクター アンド ギャンブル カンパニー | 機械的処理時の繊維又は基材の摩擦特性を評価する方法 |
FR2976804B1 (fr) | 2011-06-23 | 2013-07-12 | Oreal | Procede de traitement des fibres keratiniques avec apport de chaleur |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2990336A (en) * | 1959-10-16 | 1961-06-27 | Permanent Hair Waving Corp | Process of hair waving and preparation therefor |
US3257449A (en) * | 1961-10-24 | 1966-06-21 | Kalopissis Gregoire | Surface active amine salts |
EP0126013A1 (de) * | 1983-05-17 | 1984-11-21 | Sanofi S.A. | Zyklische Dithioacetamide, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen |
EP0368763A1 (de) * | 1988-11-09 | 1990-05-16 | L'oreal | 4-Mercapto-Butyramide-N-mono- oder N,N-disubstituiert durch ein Mono- oder Polyhydroxyalkyl-Radikal und ihre Verwendung als Reduktionsmittel zur dauernden Verformung von Haaren |
US4973475A (en) * | 1988-10-07 | 1990-11-27 | Revlon, Inc. | Hair treatment and conditioning agents |
JPH0597800A (ja) * | 1991-10-11 | 1993-04-20 | Kao Corp | メルカプト変性ラクタム誘導体及びそれを含有する毛髪処理剤組成物 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL65044C (de) * | 1941-06-16 |
-
1996
- 1996-05-08 DE DE19618445A patent/DE19618445A1/de not_active Withdrawn
-
1997
- 1997-03-01 JP JP9539457A patent/JPH11509556A/ja active Pending
- 1997-03-01 US US08/981,367 patent/US6153178A/en not_active Expired - Fee Related
- 1997-03-01 WO PCT/EP1997/001028 patent/WO1997041828A1/de not_active Application Discontinuation
- 1997-03-01 EP EP97906147A patent/EP0840592A1/de not_active Withdrawn
- 1997-03-01 ES ES97906147T patent/ES2114849T1/es active Pending
- 1997-03-01 BR BR9702246A patent/BR9702246A/pt unknown
- 1997-04-11 AR ARP970101454A patent/AR006612A1/es not_active Application Discontinuation
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2990336A (en) * | 1959-10-16 | 1961-06-27 | Permanent Hair Waving Corp | Process of hair waving and preparation therefor |
US3257449A (en) * | 1961-10-24 | 1966-06-21 | Kalopissis Gregoire | Surface active amine salts |
EP0126013A1 (de) * | 1983-05-17 | 1984-11-21 | Sanofi S.A. | Zyklische Dithioacetamide, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen |
US4973475A (en) * | 1988-10-07 | 1990-11-27 | Revlon, Inc. | Hair treatment and conditioning agents |
EP0368763A1 (de) * | 1988-11-09 | 1990-05-16 | L'oreal | 4-Mercapto-Butyramide-N-mono- oder N,N-disubstituiert durch ein Mono- oder Polyhydroxyalkyl-Radikal und ihre Verwendung als Reduktionsmittel zur dauernden Verformung von Haaren |
JPH0597800A (ja) * | 1991-10-11 | 1993-04-20 | Kao Corp | メルカプト変性ラクタム誘導体及びそれを含有する毛髪処理剤組成物 |
Non-Patent Citations (1)
Title |
---|
DATABASE WPI Section Ch Week 9320, Derwent World Patents Index; Class D21, AN 93-164433, XP002038110 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1639992A2 (de) * | 1997-01-11 | 2006-03-29 | Wella Aktiengesellschaft | Verfahren zur Herstellung von N-verzweigtkettig alkylsubstituierten Mercaptoacetamiden |
EP1639992A3 (de) * | 1997-01-11 | 2007-03-14 | Wella Aktiengesellschaft | Verfahren zur Herstellung von N-verzweigtkettig alkylsubstituierten Mercaptoacetamiden |
Also Published As
Publication number | Publication date |
---|---|
JPH11509556A (ja) | 1999-08-24 |
AR006612A1 (es) | 1999-09-08 |
DE19618445A1 (de) | 1997-11-13 |
ES2114849T1 (es) | 1998-06-16 |
BR9702246A (pt) | 1999-02-17 |
US6153178A (en) | 2000-11-28 |
EP0840592A1 (de) | 1998-05-13 |
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