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DE1617704B2 - Hair treatment preparations - Google Patents

Hair treatment preparations

Info

Publication number
DE1617704B2
DE1617704B2 DE19661617704 DE1617704A DE1617704B2 DE 1617704 B2 DE1617704 B2 DE 1617704B2 DE 19661617704 DE19661617704 DE 19661617704 DE 1617704 A DE1617704 A DE 1617704A DE 1617704 B2 DE1617704 B2 DE 1617704B2
Authority
DE
Germany
Prior art keywords
hair treatment
hair
water
formula
hydrochloride
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
DE19661617704
Other languages
German (de)
Other versions
DE1617704A1 (en
DE1617704C3 (en
Inventor
Gregoire Paris Kalopissis
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LOreal SA
Original Assignee
LOreal SA
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
Application filed by LOreal SA filed Critical LOreal SA
Publication of DE1617704A1 publication Critical patent/DE1617704A1/en
Publication of DE1617704B2 publication Critical patent/DE1617704B2/en
Application granted granted Critical
Publication of DE1617704C3 publication Critical patent/DE1617704C3/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/006—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length of peptides containing derivatised side chain amino 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • 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
    • 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
    • A61K8/4986—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with sulfur as the only hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/008—Preparations for oily skin
    • 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
    • A61Q5/006—Antidandruff preparations
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/43—Y being a hetero atom
    • C07C323/44—X or Y being nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/32—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/34—Sulfur atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Analytical Chemistry (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)

Description

Beispiel 5 HaarbehandlungsmittelExample 5 Hair treatment agents

S-Benzylcysteaminhydrochlorid der FormelS-benzylcysteamine hydrochloride der formula

C6H5-CH2-S-CH2-CH2-NH2, HCl Mit destilliertem, parfümierten WasserC 6 H 5 -CH 2 -S-CH 2 -CH 2 -NH 2 , HCl With distilled, perfumed water

auffüllen auf fill up on

Beispiel 6 HaarbehandlungsmittelExample 6 Hair treatment preparations

S-Benzylcysteaminhydrochlorid der FormelS-benzylcysteamine hydrochloride of the formula

C6H5-CH2-S-CH2-CH2-NH2, HClC 6 H 5 -CH 2 -S-CH 2 -CH 2 -NH 2 , HCl

Methionin Methionine

Mit destilliertem, parfümierten WasserWith distilled, perfumed water

auffüllen auf fill up on

0,82 g 100 ecm0.82 g 100 ecm

toto

1,5 g 0,5 g1.5 g 0.5 g

100 ecm100 ecm

2525th

3030th

B ei sp i e 1 7 HaarbehandlungsmittelEg 1 7 hair treatment products

S-Benzylcysteaminhydrochlorid der FormelS-benzylcysteamine hydrochloride of the formula

C6H5-CH2-S-CH2-CH2-NH2, HCl 1,5 g Mit destilliertem, parfümierten WasserC 6 H 5 -CH 2 -S-CH 2 -CH 2 -NH 2 , HCl 1.5 g With distilled, perfumed water

auffüllen auf 100 ecmfill up to 100 ecm

Es wird hinzugefügt:
Carbopol 1,25 gIt is added:
Carbopol 1.25 g

worauf das ganze durch einen Tropfen Ammoniak auf einen pH-Wert zwischen 8,0 und 8,2 gebracht wird. Man erhält so ein Gelee, das man in einer Menge von ungefähr 0,5 g auf eine mittelmäßig fette Kopfhaut anwenden kann.whereupon the whole thing is brought to a pH value between 8.0 and 8.2 with a drop of ammonia. In this way a jelly is obtained which can be used in an amount of approximately 0.5 g on a moderately oily scalp can.

Beispiele LotionExamples lotion

S-Tritylcysteaminhydrochlorid der FormelS-trityl cysteamine hydrochloride of the formula

(CeH6)3 C-S-CH2-CH2-NH2, HCl,(C e H 6 ) 3 CS-CH 2 -CH 2 -NH 2 , HCl,

H2O 0,75 gH 2 O 0.75 g

Dimethylhydantoinformolharz 0,5 gDimethyl hydantoin formole resin 0.5 g

Dimethyl-Dilaurylammoniumchlorid... 0,5 gDimethyl-dilaurylammonium chloride ... 0.5 g

Parfüm 0,1 gPerfume 0.1 g

Alkohol 50 ecmAlcohol 50 ecm

Mit Wasser auffüllen auf 100 ecmFill up with water to 100 ecm

Beispiel 9 LotionExample 9 Lotion

S-Benzylcysteaminhydrochlorid der FormelS-benzylcysteamine hydrochloride of the formula

C6H5-CH2-S-CH2-CH2-NH2, HCl 0,7 gC 6 H 5 -CH 2 -S-CH 2 -CH 2 -NH 2 , HCl 0.7 g

Ca-Pantothenat 0,25 gCa pantothenate 0.25 g

p-Aminobenzoesäure 0,25 gp-aminobenzoic acid 0.25 g

Polyäthylenglykol 300 5 gPolyethylene glycol 300 5 g

Parfüm 0,1 gPerfume 0.1 g

Alkohol 50 ecmAlcohol 50 ecm

Mit Wasser auffüllen auf 100 ecmFill up with water to 100 ecm

4040

4545

5555

6060

Beispiel 10Example 10

FrisiergeleeStyling jelly

S-Tritylcysteaminhydrochlorid der Formel
(C6Hs)-C-S-CH2-CH2-NH2, HCl,S-trityl cysteamine hydrochloride of the formula
(C 6 Hs) -CS-CH 2 -CH 2 -NH 2 , HCl,

H2O 0,25 gH 2 O 0.25 g

Menthylpantothenat 0,2 gMenthyl pantothenate 0.2 g

Carbopol 940 0,5 gCarbopol 940 0.5 g

Polyvinylpyrrolidon 3 gPolyvinylpyrrolidone 3 g

Propylenglykol 10 gPropylene glycol 10 g

Triäthanolamin bis zu einem pH-Wert 8Triethanolamine up to a pH value of 8

Parfüm 0,1 gPerfume 0.1 g

Alkohol 20 ecmAlcohol 20 ecm

Konservierungsmittel auf Grundlage von Methylparaoxybenzoat, HandelsnamePreservative based on methyl paraoxybenzoate, trade name

»Nipagine« 0,10 g"Nipagine" 0.10 g

Konservierungsmittel auf Grundlage von Propylparaoxybenzoat, HandelsnamePreservative based on propyl paraoxybenzoate, trade name

»Nipasol« 0,10 g"Nipasol" 0.10 g

Brom-2-nitro-2-propandiol 1-3 0,3 gBromo-2-nitro-2-propanediol 1-3 0.3 g

Mit Wasser auffüllen auf 100 ecmFill up with water to 100 ecm

Beispiel 11 FrisiergeleeExample 11 Hairdressing jelly

S-Benzylcysteaminhydrochlorid der Formel
C8H5-CH2-S-CH2-CH2-NH2, HCl, 0,4 gS-benzylcysteamine hydrochloride of the formula
C 8 H 5 -CH 2 -S-CH 2 -CH 2 -NH 2 , HCl, 0.4 g

Carbopol 940 0,45 gCarbopol 940 0.45 g

Polyvinylpyrrolidon 2 gPolyvinylpyrrolidone 2 g

Oxyäthyleniertes Wollfett IgOxyethylene wool fat Ig

Polyäthylenglykol 300 5 gPolyethylene glycol 300 5 g

Konservierungsmittel auf der Grundlage von Methylparaoxybenzoat, verkauftPreservatives based on methyl paraoxybenzoate, sold

unter der Marke »Nipagine« 0,10 gunder the brand »Nipagine« 0.10 g

Konservierungsmittel auf der Grundlage von Propylparaoxybenzoat, im HandelPreservatives based on propyl paraoxybenzoate, commercially available

unter dem Namen »Nipasol« 0,10 gunder the name "Nipasol" 0.10 g

Parfüm 0,1 gPerfume 0.1 g

Triäthanolamin, bis zum pH-Wert 8Triethanolamine, up to pH 8

Mit Wasser auffüllen auf 100 ecmFill up with water to 100 ecm

Beispiel 12 CremeExample 12 cream

S-Benzylcysteaminhydrochlorid der FormelS-benzylcysteamine hydrochloride of the formula

C6H5-CH2-S-CH2-CH2-NH2, HCl, 2 g Oxyäthylenierter Cetylstearylalkohol ..7gC 6 H 5 -CH 2 -S-CH 2 -CH 2 -NH 2 , HCl, 2 g oxyethylenated cetostearyl alcohol ..7g

Silikonöl IgSilicone oil Ig

Diäthylenglykolstearat 6 gDiethylene glycol stearate 6 g

Konservierungsmittel auf Grundlage von Methylparaoxybenzoat, im Handel unter dem Namen »Nipagine« 0,10 gPreservative based on methyl paraoxybenzoate, commercially available under the name "Nipagine" 0.10 g

Konservierungsmittel auf Grundlage von Propylparaoxybenzoat, im Handel unter dem Namen »Nipasol« 0,10 gPreservative based on propyl paraoxybenzoate, commercially available at the name "Nipasol" 0.10 g

Mit Wasser auffüllen auf 100 ecmFill up with water to 100 ecm

Beispiel 13 Milch gegen AkneExample 13 Milk for acne

S-Tritylcysteaminhydrochlorid der Formel
(C6Hs)3 C-S—CH2—CH2—InH2, JrICl,S-trityl cysteamine hydrochloride of the formula
(C 6 Hs) 3 CS — CH 2 —CH 2 —InH 2 , JrICl,

H2O 2 gH 2 O 2 g

Carbopol 934 0,375 gCarbopol 934 0.375 g

Isopropylester von Wollfettsäuren IgIsopropyl ester of wool fatty acids Ig

Oxyäthyleniertes Wollfett 2,5 gOxyethylene wool fat 2.5 g

Oxyäthylenierter Cetylstearylalkohol ...3gOxyethylene cetostearyl alcohol ... 3g

Substituiertes Alcoylamid 2 gSubstituted alcoylamide 2 g

Alkohol 20 ecmAlcohol 20 ecm

Triäthanolamin, auffüllen auf einen pH-Wert von Konservierungsmittel auf Grundlage von Methylparaoxybenzoat, im Handel unter dem Namen »Nipagine« 0,10 gTriethanolamine, replenish to a pH based preservative Methyl paraoxybenzoate, commercially available under the name "Nipagine" 0.10 g

Konservierungsmittel auf Grundlage von Propylparaoxybenzoat, im Handel unter dem Namen »Nipasol« 0,10 gPreservative based on propyl paraoxybenzoate, commercially available at the name "Nipasol" 0.10 g

Mit Wasser auffüllen auf 100 ecmFill up with water to 100 ecm

Beispiel 14Example 14

Es wird ein Haarbehandlungsmittel mit folgender Zusammensetzung hergestellt:A hair treatment agent is made with the following composition:

S-Benzylcysteaminmalat der Formel C6H5-CH2-S-CH2-CH2-NH2,S-benzylcysteamine malate of the formula C 6 H 5 -CH 2 -S-CH 2 -CH 2 -NH 2 ,

HO2C-CH2-CHOH-CO2H 1,3 gHO 2 C-CH 2 -CHOH-CO 2 H 1.3 g

Polyäthylenglykol 300 5 gPolyethylene glycol 300 5 g

Parfüm 0,1 gPerfume 0.1 g

Alkohol 45 cm3 Alcohol 45 cm 3

Mit Wasser auffüllen auf 100 cm3 Make up to 100 cm 3 with water

Bei dem in diesem Haarbehandlungsmittel verwendeten S-Benzylcysteaminmalat handelt es sich um aus Äthanol kristallisierte weiße Kristalle mit einem Schmelzpunkt von 112° C, die in Wasser löslich sind.The S-benzyl cysteamine malate used in this hair treatment agent is from Ethanol crystallized white crystals with a melting point of 112 ° C, which are soluble in water.

Beispiel 15Example 15

Es wird ein Haarbehandlungsmittel mit folgender Zusammensetzung hergestellt:A hair treatment agent is made with the following composition:

S-Benzylcysteaminnicotinat der Formel C6H6-CH2-S-CH2-CH2-NH2, HO2C-/\ IgS-benzyl cysteamine nicotinate of the formula C 6 H 6 -CH 2 -S-CH 2 -CH 2 -NH 2 , HO 2 C - / \ Ig

Dimethylhydantion-Formol-Harz 0,5 gDimethylhydantione formol resin 0.5 g

Dimethyldilaurylammoniumchlorid ... 0,5 gDimethyldilaurylammonium chloride ... 0.5 g

Parfüm 0,1 gPerfume 0.1 g

Alkohol 60 cm3 Alcohol 60 cm 3

Mit Wasser auffüllen auf 100 cm3 Make up to 100 cm 3 with water

Bei dem in diesem Haarbehandlungsmittel verwendeten S-Benzylcysteaminnicotinat handelt es sich um aus Äthylacetat kristallisierte weiße Nadeln mit einem Schmelzpunkt von 106° C, die in Wasser und Alkoholen löslich sind.The S-benzyl cysteamine nicotinate used in this hair treatment agent is from ethyl acetate crystallized white needles with a melting point of 106 ° C, which in water and alcohols are soluble.

Bei dem in diesem Haarbehandlungsmittel verwendeten S-Benzylcysteaminhydrobromid handelt es sich um aus Dichloräthan kristallisierte weiße Kristalle mit einem Schmelzpunkt von 1300C, die in Wasser und Alkoholen löslich sind.The material used in this hair treatment agent S-Benzylcysteaminhydrobromid is crystallized from dichloroethane white crystals having a melting point of 130 0 C, which are soluble in water and alcohols.

Beispiel 17Example 17

Es wird ein Haarbehandlungsmittel mit folgender Zusammensetzung hergestellt:A hair treatment agent is made with the following composition:

S-Benzylcysteaminditartrat 0,25 gS-benzyl cysteamine ditrate 0.25 g

Menthylpantothenat 0,2 gMenthyl pantothenate 0.2 g

vernetzte Polyacrylsäure (vertrieben untercross-linked polyacrylic acid (sold under

der Handelsmarke CARBOPOL 940) 0,5 gof the trademark CARBOPOL 940) 0.5 g

Polyvinylpyrrolidon 3 gPolyvinylpyrrolidone 3 g

Propylenglykol 10 gPropylene glycol 10 g

Mit Triäthanolamin auffüllen bis pH 8Top up with triethanolamine to pH 8

Parfüm 0,1 gPerfume 0.1 g

Alkohol 20 cm3 Alcohol 20 cm 3

p-Hydroxybenzoesäuremethylester 0,10 gmethyl p-hydroxybenzoate 0.10 g

p-Hydroxybenzoesäurepropolyester ... 0,10 gp-Hydroxybenzoic acid propolyester ... 0.10 g

Mit Wasser auffüllen auf 100 cm3 Make up to 100 cm 3 with water

Bei dem in diesem Haarbehandlungsmittel verwendeten S-Benzylcysteaminditartrat handelt es sich um aus einer Mischung von Wasser und Äthanol kristallisierte weiße Nandeln mit einem Schmelzpunkt von 1670C, die in Äthanol unlöslich, in Wasser jedoch löslich sind.The material used in this hair treatment agent S-Benzylcysteaminditartrat is a mixture of water and ethanol crystallized white Nandeln having a melting point of 167 0 C, which are soluble in ethanol but insoluble in water.

B ei spi el 18Example 18

Es wird ein Haarbehandlungsmittel mit folgender Zusammensetzung hergestellt:A hair treatment agent is made with the following composition:

S-Benzylcysteaminsalicylat 0,9 gS-benzyl cysteamine salicylate 0.9 g

Mit destilliertem parfümiertem Wasser auffüllen auf 100 cm3 Make up to 100 cm 3 with distilled perfumed water

Bei dem in diesem Haarbehandlungsmittel verwendeten S-Benzylcysteaminsalicylat handelt es sich um weiße Nadeln mit einem Schmelzpunkt von 124 bis 126° C, die in Äthanol und wäßrigalkoholischen Lösungen löslich und in Wasser wenig löslich sind.The S-benzyl cysteamine salicylate used in this hair treatment agent is white needles with a melting point of 124 to 126 ° C, which are in ethanol and aqueous alcoholic solutions are soluble and sparingly soluble in water.

Beispiel 19Example 19

Es wird ein Haarbehandlungsmittel mit folgender Zusammensetzung hergestellt:A hair treatment agent is made with the following composition:

S-Benzylcysteamin-p-toluolsulfonat 1,5 gS-benzyl cysteamine p-toluenesulfonate 1.5 g

Methionin 0,5 gMethionine 0.5 g

Mit destilliertem parfümiertem WasserWith distilled perfumed water

auffüllen auf 100 cm3 fill up to 100 cm 3

Bei dem in diesem Haarbehandlungsmittel verwendeten S-Benzylcysteamin-p-toluolsulfonat handelt es sich um durch Kristallisation in einer Mischung von Äthanol und Äther erhaltene weiße Kristalle mit einem Schmelzpunkt von 126 bis 1300C, die in Wasser und Äthanol löslich sind.The S-benzylcysteamine-p-toluenesulfonate used in this hair treatment agent is white crystals obtained by crystallization in a mixture of ethanol and ether with a melting point of 126 to 130 ° C., which are soluble in water and ethanol.

Beispiel 16. 6o Beispiel 20Example 16. 6o Example 20

Es wird ein Haarbehandlungsmittel mit folgender Es wird ein Haarbehandlungsmittel mit folgenderIt becomes a hair treatment agent with the following. It becomes a hair treatment agent with the following

Zusammensetzung hergestellt: . Zusammensetzung hergestellt:Composition made:. Composition made:

S-Benzylcysteaminhydrobromid der FormelS-benzylcysteamine hydrobromide of the formula

C6H8-CH2-S-CH2-CH2-NH2, BrH 5 g Mit destilliertem parfümiertem WässerC 6 H 8 -CH 2 -S-CH 2 -CH 2 -NH 2 , BrH 5 g With distilled perfumed water

auffüllen auf 100 cm3 fill up to 100 cm 3

S-Benzylcysteaminphosphat 1,3 gS-benzyl cysteamine phosphate 1.3 g

Polyäthylenglykol 300 5 gPolyethylene glycol 300 5 g

Parfüm 0,1 gPerfume 0.1 g

Alkohol 45 cm3 Alcohol 45 cm 3

Mit Wasser auffüllen auf ... 100 cm3 Fill up with water to ... 100 cm 3

7 87 8

Bei dem in diesem Haarbehandlungsmittel verwen- Das in diesem Haarbehandlungsmittel verwendeteThe one used in this hair treatment agent The used in this hair treatment agent

deten S-Benzylcysteaminphosphat handelt es sich um S-Amino-S-thiapentansäurebutylester-hydrochlorid istThe S-benzylcysteamine phosphate is S-amino-S-thiapentanoic acid butyl ester hydrochloride

aus einer Mischung von Wasser und Äthanol kristalli- bei gewöhnlicher Temperatur eine Flüssigkeit, die sichfrom a mixture of water and ethanol crystalline at ordinary temperature a liquid, which

sierte weiße Nadeln mit einem Schmelzpunkt von bei 0° C verfestigt und die bei 18O0C unter Zersetzungcatalyzed white needles solidified with a melting point of 0 ° at the C and at 18O 0 C with decomposition

142° C, die in Äthanol unlöslich, in Wasser jedoch 5 verdampft. Sie ist in Alkohol löslich und in Wasser142 ° C, which is insoluble in ethanol, but evaporates 5 in water. It is soluble in alcohol and in water

löslich sind. wenig löslich.are soluble. sparingly soluble.

. , . ■ Statt der in den vorstehenden Beispielen eingesetzten. ,. ■ Instead of those used in the previous examples

ispiel aktiven Komponenten kann beispielsweise auch dasIspiel active components can, for example, also do that

Es wird ein Haarbehandlungsmittel mit folgender S-Benzylcysteamindicitrat eingesetzt _werden, bei demA hair treatment agent with the following S-benzylcysteamine citrate is used in which

Zusammensetzung hergestellt: io es sich um durch Kristallisation aus Äthanol erhalteneComposition made: it is obtained by crystallization from ethanol

S-Amino-a-thiapentansäure-methylester- Γ^^?*11^ Τ"?· Schmelzpunkt von HO0CS-Amino-a-thiapentanoic acid methyl ester- Γ ^^? * 11 ^ Τ "? · Melting point of HO 0 C

hydrochlorid der Formel ha"delt>. d.ie in Wafer losllch,smd-.. hydrochloride of formula ha "delt> d ie in Wa he f losllch, smd -

CH3O-CO-Ch2-S-CH2-CH2-NH2, , Toxizitatsversuche mit dem erfindungsgemaßenCH 3 O-CO-Ch 2 -S-CH 2 -CH 2 -NH 2 ,, Toxicity tests with the inventive

TiQ 2 5g kosmetischen Mittel wurden einerseits mit männlichenTiQ 2 5g cosmetic products were used on the one hand with male

Methionin 075 e 15 Wistarratten, die ungefähr 6 Wochen alt waren undMethionine 075 e 15 Wistar rats that were about 6 weeks old and

Mit destilliertem parfümiertem Wasser ' u"gefähr 1(?° 8 W0Sen> und andererseits mit gewöhnli-With distilled perfumed water ' u " about 1 ( ? ° 8 W0 S en > and on the other hand with ordinary

auffüllen auf 100 cm3 mannlichen weißen Mausen mit einem Gewichtfill up to 100 cm 3 weighing male white mice

von ungefähr 20 g durchgeführt.of approximately 20 g.

Bei dem in diesem Haarbehandlungsmittel verwen- Drei Gruppen von 20 Tieren jeder Gattung wurdeThe three groups of 20 animals of each genus were used in this hair treatment agent

deten S-Amino-S-thiapentansäure-methylester-hydro- 20 eine subkutane Injektion pro Tier von jeweils
chlorid handelt es sich um durch Kristallisation ausdeten S-amino-S-thiapentanoic acid methyl ester hydro-20 one subcutaneous injection per animal of each
chloride is a result of crystallization

einer Mischung von Methanol und Äthylacetat erhal- a) s.Carboxymethylcysteamin in einer Menge vona mixture of methanol and ethyl acetate obtained a) s.Carboxymethylcysteamin in an amount of

tene weiße Plättchen mit einem Schmelzpunkt von ■, IV f·· Hi t n tene white platelets with a melting point of ■, IV f ·· Hi tn

100°C, die in Wasser und Äthanol löslich sind. 1 g/kg tUr die erSte °Γυρρε'100 ° C, which are soluble in water and ethanol. 1 g / kg for the FIRST ° Γυρρε '

25 b) S-Tritylcysteaminhydrochlorid in einer Menge von25 b) S-tritylcysteamine hydrochloride in an amount of

B e i s ρ i e 1 22 0,5 g/kg Lebendgewicht für die zweite Gruppe,B e i s ρ i e 1 22 0.5 g / kg live weight for the second group,

Es wird ein Haarbehandlungsmittel mit folgender c) S-Benzylcysteaminhydrochlorid in einer MengeIt becomes a hair treatment agent containing the following c ) S-benzylcysteamine hydrochloride in an amount

Zusammensetzung hergestellt: von 0,15 kg/ Lebendgewicht für die dritte GruppeComposition made: from 0.15 kg / live weight for the third group

S-Amino-S-thiapentansäurebutylester- 30S-Amino-S-thiapentanoic acid butyl ester- 30

hydrochlorid der Formel verabreicht, und innerhalb von 72 Stunden wurde beihydrochloride of the formula administered, and within 72 hours was at

C4H9OCO-CH2-S-CH2-CH2-NH2, keinem der Tiere der Tod festgestellt.C 4 H 9 OCO-CH 2 -S-CH 2 -CH 2 -NH 2 , none of the animals found death.

HCl Ig Außerdem hat man keinerlei Reizwirkung auf derHCl Ig In addition, there is no irritating effect on the

Dimethylhydantoin-Formol-Harz 0,5 g Haut dieser Tiere festgestellt, woraus zu schließen ist,Dimethylhydantoin formol resin 0.5 g skin of these animals found, from which it can be concluded

Dimethyldilaurylammoniumchlorid ... 0,5 g 35 daß die neuen kosmetischen Mittel nicht toxisch sind.Dimethyldilaurylammoniumchlorid ... 0.5 g 35 that the new cosmetic products are not toxic.

Parfüm 0,1 g Die am Menschen durchgeführten Versuche habenPerfume 0.1 g The experiments carried out on humans have

Alkohol 60 cm3 bestätigt, daß die neuen kosmetischen Mittel die HautAlcohol 60 cm 3 confirms that the new cosmetic means the skin

Mit Wasser auffüllen auf 100 cm3 nicht angreifen.Fill up with water to 100 cm 3 do not attack.

Claims (2)

1 2 Schuppen, unerwünschten Talgansammlungen, bePatentansprüche: dingt durch übermäßige Talgdrüsensekretion und meist von mehr oder weniger starkem Haarausfall be-1 2 Dandruff, unwanted sebum build-up, patent claims: caused by excessive sebum secretion and usually more or less severe hair loss 1. Haarbehandlungsmittel, gekennzeich- gleitet, und ähnlichen im wesentlichen durch Seborrhoe net durch einen Gehalt an Wirkstoffen der 5 verursachten unerwünschten und wenig ästhetischen Formel Zuständen. ,Versuche mit einem erfindungsgemäßen1. Hair treatment agents, marked slides, and the like, essentially due to seborrhea net undesirable and unaesthetic caused by a content of active ingredients of the 5 Formula states. , Experiments with an inventive Haarbeharidlungsmittel in Form eines Haarwassers R — S — CH2 — CH2 — NH2 haben dabei gezeigt, daß bei Behandlung mit einemHair treatment agents in the form of a hair lotion R - S - CH 2 - CH 2 - NH 2 have shown that when treated with a derartigen erfindungsgemäßen Haarbehandlungsmittelsuch hair treatment compositions according to the invention worin R das Radikal — CH2 — C6H5, das Radikal io das fettige Aussehen der behandelten Haare vorteil-— CH2 — COOH oder das Radikal — C(CeH5)3 haft verbessert wird, die behandelten Haare werden bedeutet. weniger schnell wieder fett, und eine Wasserwelle hältwhere R is the radical - CH 2 - C 6 H 5 , the radical io the greasy appearance of the treated hair is advantageously - CH 2 - COOH or the radical - C (C e H 5 ) 3 is improved, the treated hair means . grease again less quickly, and a water wave lasts 2. Haarbehandlungsmittel nach Anspruch 1, da- in den behandelten Haaren besser.2. Hair treatment agent according to claim 1, in that the treated hair is better. durch gekennzeichnet, daß es eine Konzentration Es ist bereits die Verwendung von synthetischencharacterized by that there is a concentration It is already the use of synthetic an aktivem Wirkstoff zwischen 0,5 und 5%, vor- 15 Verbindungen auf Schwefelbasis als kosmetische zugsweise zwischen 1,5 und 2%, aufweist. Mittel gegenüber fettem Haar vorgeschlagen worden,of active ingredient between 0.5 and 5%, preferably 15 sulfur-based compounds as cosmetic preferably between 1.5 and 2%. Remedies for oily hair have been proposed, die Mehrzahl der bisher zu diesem Zweck verwendeten Stoffe befriedigen jedoch nicht in allen Fällen und sindhowever, the majority of the substances hitherto used for this purpose do not and are not satisfactory in all cases im allgemeinen nicht für die erforderliche Zeit be-generally not loaded for the required time 20 ständig.20 constantly. Die erfindungsgemäß eingesetzten Wirkstoffe be-The active ingredients used according to the invention are Die vorliegende Erfindung betrifft ein Haarbehand- sitzen gegenüber den bisher bekannten Produkten den lungsmittel mit einem Gehalt an Wirkstoffen der Vorteil, daß sie in Wasser oder einige davon in einer Formel 50 %igen alkoholischen Lösung löslich sind.The present invention relates to a hair treatment compared to the previously known products Agents with an active ingredient content have the advantage that they are in water or some of them in one Formula 50% alcoholic solution are soluble. η ο £TT ££j JnJJj 25 Die erfindungsgemäßen Haarbehandlungsmittel ha-η ο £ TT ££ j J n JJj 25 The hair treatment compositions according to the invention have 222 ben auch die vorteilhafte Eigenschaft, Haarausfall zu 222 also have the beneficial property of causing hair loss verhindern.impede. worin R das Radikal — CH2 — C8H5, das Radikal Zur Anwendung können die erfindungsgemäßenwherein R is the radical - CH 2 - C 8 H 5 , the radical — CH2 — COOH oder das Radikal — C(CeH5)3 be- Haarbehandlungsmittel auf die Kopfhaut aufgebracht deutet. Die Konzentration an aktivem Wirkstoff in dem 30 werden.- CH 2 - COOH or the radical - C (C e H 5 ) 3 indicates that hair treatment agents are applied to the scalp. The concentration of active ingredient in the 30 will be. erfindungsgemäßen Haarbehandlungsmittelliegtzweck- Die nachfolgenden Beispiele erläutern die Ermäßigerweise zwischen 0,5 und 5 % und vorzugsweise findung,
zwischen 1,5 und 2%. Die Wirkstoffe in dem erfindungsgemäßen Haarbehandlungsmittel können dabei Beispiel 1 als freie Basen, sofern diese freien Basen nicht toxisch 35 . sind, oder in Form ihrer Salze mit einer organischen Haarbehandlungsmittel Säure oder einer Mineralsäure, wie Chlorwasserstoff- In 100 ecm destilliertem parfümiertem Wasser sind säure, Anwendung finden. Enthält der in den er- 1,5 g S-Carboxymethyl-cysteamin der FormelHair treatment agent according to the invention is the purpose of the following examples explain the use of between 0.5 and 5 % and preferably the invention,
between 1.5 and 2%. The active ingredients in the hair treatment composition according to the invention can be used in Example 1 as free bases, provided that these free bases are not toxic. are, or in the form of their salts with an organic hair treatment agent acid or a mineral acid such as hydrogen chloride- In 100 ecm of distilled perfumed water are acid, use. Contains the 1.5 g S-carboxymethyl-cysteamine of the formula findungsgemäßen Haarbehandlungsmitteln eingesetzte COOH CH S CH CH NHhair treatment agents according to the invention used COOH CH S CH CH NH Wirkstoff eine Carboxylgruppe, so können auch Ester 40 2222Active ingredient a carboxyl group, so can ester 40 2222 davon Anwendung finden, wobei derartige veresterte enthalten. Produkte eine verbesserte Lipoidlöslichkeit zeigen.of which find application, such as containing esterified. Products show improved lipoid solubility. Zu den erfindungsgemäß einsetzbaren Wirkstoffen Beispiel 2Example 2 of the active ingredients which can be used according to the invention gehören insbesondere S-Carboxymethylcysteamin undinclude in particular S-carboxymethylcysteamine and dessen Hydrochlorid, S-Trilylcysteamin und dessen 45 Haarbehandlungsmittelits hydrochloride, S-trilylcysteamine and its 45 hair treatment agents Hydrochlorid sowie S-Benzylcysteamin und dessen S-Carboxymethyl-cysteamin der FormelHydrochloride and S-benzylcysteamine and its S-carboxymethyl-cysteamine of the formula Hydrochlorid. COOH-Ch2-S-CH2-CH2-NH2 .... 0,54gHydrochloride. COOH-Ch 2 -S-CH 2 -CH 2 -NH 2 .... 0.54g Die erfindungsgemäßen Haarbehandlungsmittel kön- Methionin 0,50 gThe hair treatment agents according to the invention can methionine 0.50 g nen in Form von Lotionen, Haarwassern, als Salben, Mit destilliertem, parfümiertem Wasserin the form of lotions, hair lotions, as ointments, with distilled, perfumed water Cremes, Pomaden, Brillantinen, als Gelee, in Form 50 auffüllen auf 100 ecmCreams, pomades, brillantines, as jelly, in form 50 fill up to 100 ecm einer Suspension, Dispersion oder Lösung in Wasser,a suspension, dispersion or solution in water, Wasser-Alkohol-Mischungen oder öl oder in jeder B e i s ρ i e 1 3Water-alcohol mixtures or oil or in any way 1 3 anderen geeigneten kosmetischen Zubereitungsform .other suitable cosmetic preparation form. vorliegen. In Frage kommen insbesondere Lösungen der Haarbehandlungsmittelare present. In particular, solutions of the hair treatment agents come into consideration erfindungsgemäß eingesetzten Wirkstoffe in Wasser 55 In 100 ecm einer 50%igen wäßrigalkoholischenAccording to the invention used active ingredients in water 55 in 100 ecm of a 50% aqueous alcoholic oder alkoholischen Lösungen sowie Lösungen oder Lösung sind 1,5 g Chlorhydrat von S-Trityl-cysteaminor alcoholic solutions as well as solutions or solutions are 1.5 g of S-trityl-cysteamine hydrochloride Dispersionen in kosmetischen ölen, Cremes oder der FormelDispersions in cosmetic oils, creams or the formula Gelees. In allen Fällen können die erfindungsgemäßen er1 u λ η c rnx nvs υπ unJellies. In all cases, the invention can be 1 u λ η c rnx nvs υπ un TT L L Ji -.n. 1 j Lj (LeJtI5J3 — C — o — CJTl2 — V-JtI2, JtICl, H2UTT LL Ji -.n. 1 j Lj (LeJtI 5 J 3 - C - o - CJTl 2 - V-JtI 2 , JtICl, H 2 U Haarbehandlungsmittel einen oder mehrere der erfindungsgemäß eingesetzten Wirkstoffe enthalten, wo- 60 enthalten,
bei auch weitere Stoffe vorliegen können, beispielsweise B e i s ρ i e 1 4 in der Kosmetik allgemein verwendete Komponenten TT , , ,. . , wie Penetrationsmittel, Netzmittel, Parfüms, Färb- Haarbehandlungsmittel stoffe od. dgl. S-Benzylcysteamin-hydrochlorid derHair treatment agents contain one or more of the active ingredients used according to the invention, including 60,
where other substances may also be present, for example B eis ρ ie 1 4 components commonly used in cosmetics TT,,, . . such as penetrants, wetting agents, perfumes, dye hair treatment agents od. Like. S-Benzylcysteamine hydrochloride Die erfindungsgemäßen Haarbehandlungsmittel be- 65 FormelThe hair treatment compositions according to the invention have a formula sitzen ausgezeichnete kosmetische Wirksamkeit in C6H5-CH2-S-CH2-CH2-NH2, HCl 1,5 gsit excellent cosmetic effectiveness in C 6 H 5 -CH 2 -S-CH 2 -CH 2 -NH 2 , HCl 1.5 g Hinblick auf eine Herabsetzung und Beseitigung des Methionin 0,10 gWith a view to reducing and eliminating methionine 0.10 g fettigen Aussehens der Haare sowie der Beseitigung von Mit destilliertem Wasser auffüllen auf... 100 ecm .·.;oily appearance of the hair as well as the removal of top up with distilled water to ... 100 ecm. · .;
DE19661617704 1965-12-22 1966-12-20 Hair treatment preparations Expired DE1617704C3 (en)

Applications Claiming Priority (1)

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LU50125A LU50125A1 (en) 1965-12-22 1965-12-22

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AT (1) AT282066B (en)
AU (1) AU418744B1 (en)
BE (1) BE691589A (en)
CH (2) CH468187A (en)
DE (1) DE1617704C3 (en)
FR (2) FR6936M (en)
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IT (1) IT975504B (en)
LU (1) LU50125A1 (en)
NL (2) NL6618039A (en)

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LU55371A1 (en) * 1968-01-29 1969-08-21 Oreal
BE733993A (en) * 1968-06-14 1969-12-03
LU58042A1 (en) * 1969-02-19 1970-09-09 Oreal
LU58634A1 (en) * 1969-05-12 1971-03-09 Oreal
BE755674A (en) * 1969-09-04 1971-03-03 Oreal NEW COMPOUNDS DERIVED FROM PYRIDINE AND COSMETIC COMPOSITIONS CONTAINING THEM
DE2824249A1 (en) * 1978-06-02 1979-12-06 Agfa Gevaert Ag PRODUCTION OF PHOTOGRAPHICAL MATERIALS
US4388475A (en) 1979-08-15 1983-06-14 Merck & Co., Inc. Allylsulfoxide enzyme inhibitors
US4558071A (en) * 1979-08-15 1985-12-10 Merck & Co., Inc. Phenyl, trihalomethyl or heteroaryl sulfoxides having a latent allyl group bound to sulfur as enzyme inhibitors
EP0159519A3 (en) * 1984-03-29 1987-02-04 Asta-Werke Aktiengesellschaft Chemische Fabrik Use of thio compounds for the prevention of hair fall-out caused by cytostatics
US5298483A (en) * 1992-03-30 1994-03-29 Tropicana Products, Inc. New matter of composition and method for using the same as plant bioregulators
FR2740340B1 (en) * 1995-10-30 1997-12-05 Oreal USE OF CARBOXYLIC ACIDS CARRYING A SULFURED FUNCTION TO PROMOTE SKIN DEQUAMATION OR STIMULATE EPIDERMAL RENEWAL
US5683705A (en) * 1996-03-29 1997-11-04 Estee Lauder, Inc. Sulfur-based amides and bis-amides useful against skin disorders

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JPS5335922B1 (en) 1978-09-29
DE1617704C3 (en) 1980-09-25
BE691589A (en) 1967-06-21
GB1161349A (en) 1969-08-13
CH468187A (en) 1969-02-15
AT282066B (en) 1970-06-10
IT975504B (en) 1974-08-10
FR6936M (en) 1969-05-12
CH474494A (en) 1969-06-30
NL131093C (en)
LU50125A1 (en) 1967-06-22
FR1505874A (en) 1967-12-15
AU418744B1 (en) 1968-06-27
NL6618039A (en) 1967-06-23

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