DE1617704C3 - Hair treatment preparations - Google Patents

Hair treatment preparations

Info

Publication number
DE1617704C3
DE1617704C3 DE19661617704 DE1617704A DE1617704C3 DE 1617704 C3 DE1617704 C3 DE 1617704C3 DE 19661617704 DE19661617704 DE 19661617704 DE 1617704 A DE1617704 A DE 1617704A DE 1617704 C3 DE1617704 C3 DE 1617704C3
Authority
DE
Germany
Prior art keywords
hair treatment
hair
water
active ingredients
radical
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.)
Expired
Application number
DE19661617704
Other languages
German (de)
Other versions
DE1617704B2 (en
DE1617704A1 (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

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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)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biochemistry (AREA)
  • Cosmetics (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

enthalten.contain.

Beispiel 2
HaarbehandlungsmittelExample 2
Hair treatment preparations

S-Carboxymethyl-cysteamin der Formel
HOOC- CH2- S - CH2 - CH2- NH2 0,54 gS-carboxymethyl-cysteamine of the formula
HOOC- CH 2 - S - CH 2 - CH 2 - NH 2 0.54 g

Methionin 0,50 gMethionine 0.50 g

Mit destilliertem, parfümiertem Wasser
so auffüllen auf 100 ecmWith distilled, perfumed water
so fill up to 100 ecm

Beispiel 3
HaarbehandlungsmittelExample 3
Hair treatment preparations

In 100 ecm einer 50 %igen wäßrigalkoholischen Lösung sind 1,5 g Chlorhydrat von S-Trityl-cysteamin der FormelIn 100 ecm of a 50% aqueous alcoholic The solution is 1.5 g of S-trityl-cysteamine hydrochloride of the formula

(CeH6)3 — C — S — CH2 — CH2, HCl, H2O(C e H 6 ) 3 - C - S - CH 2 - CH 2 , HCl, H 2 O

enthalten,contain,

Beispiel 4Example 4

HaarbehandlungsmittelHair treatment preparations

S-Benzylcysteamin-hydrochlorid der
FormelS-Benzylcysteamine hydrochloride der
formula

C6H0-CH2-S-CH2-CH2-Nh^HCI 1,5 gC 6 H 0 -CH 2 -S-CH 2 -CH 2 -Nh ^ HCl 1.5g

Methionin 0,10 gMethionine 0.10 g

Mit destilliertem Wasser auffüllen auf... 100 ecmMake up to ... 100 ecm with distilled water

1616

Beispiel 5Example 5

HaarbehandlungsmittelHair treatment preparations

S-Benzylcysteaminhydrochlorid der FormelS-benzylcysteamine hydrochloride der formula

CeHs-CH2-S-CH2-CH2-NH25HCl 0,82 g Mit destilliertem, parfümierten WasserCeHs-CH 2 -S-CH 2 -CH 2 -NH 25 HCl 0.82 g With distilled, perfumed water

auffüllen auf 100 ecmfill up to 100 ecm

Beispiel 6 HaarbehandlungsmittelExample 6 Hair treatment agents

S-Benzylcysteaminhydrochlorid der FormelS-benzylcysteamine hydrochloride of the formula

C6H5-CH2-S-CH2-CH2-NH2, HCl 1,5 gC 6 H 5 -CH 2 -S-CH 2 -CH 2 -NH 2 , HCl 1.5 g

Methionin 0,5 gMethionine 0.5 g

Mit destilliertem, parfümierten WasserWith distilled, perfumed water

auffüllen auf 100 ecmfill up to 100 ecm

Beispiel 7 HaarbehandlungsmittelExample 7 Hair Treatment Agents

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.

Beispiel 8 LotionExample 8 Lotion

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

(C8Hs)3C-S-CH2-CH2-NH2, HCl,(C 8 Hs) 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.ccmFill up with water to 100.ccm

Beispiel 9 LotionExample 9 lotion

S-Benzylcysteaminhydrochlorid der FormelS-benzylcysteamine hydrochloride of the formula

C6H6-CH2-S-CH2-CH2-Nh2, HCl 0,7 gC 6 H 6 -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

Beispiel 10 FrisiergeleeExample 10 Styling 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,

7 7047 704

H2O 0,25gH 2 O 0.25g

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 °.l 8Perfume ° .l 8

Alkohol 20 ecmAlcohol 20 ecm

Konservierungsmittel auf Grundlage von ι ο p-Hydroxybenzoesäuremethylester,Preservative based on ι ο p-hydroxybenzoic acid methyl ester,

Handelsname »Nipagine« 0,10 gTrade name »Nipagine« 0.10 g

Konservierungsmittel auf Grundlage von p-Hydroxybenzoesäurepropylester,Preservative based on propyl p-hydroxybenzoate,

Handelsname »Nipasol« 0,10 gTrade name "Nipasol" 0.10 g

2-Brom-2-nitro-l,3-propandiol 0,3 g2-Bromo-2-nitro-1,3-propanediol 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
C6H5-CH2-S-CH2-CH2-NH2, HCl, 0,4 gS-benzylcysteamine hydrochloride of the formula
C 6 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 Grundlage von p-Hydroxybenzoesäuremethylester, im Handel unter dem Namen »Nipagine« 0,10 gPreservative based on methyl p-hydroxybenzoate, commercially available under the name "Nipagine" 0.10 g

Konservierungsmittel auf Grundlage von p-Hydroxybenzoesäurepropylester, im Handel unter dem Namen »Nipa-Preservative based on propyl p-hydroxybenzoate, in trade under the name »Nipa-

sol« 0,10 gsol «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

B e i s ρ i e 1 12B e i s ρ i e 1 12

Cremecream

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 of oxyethylene cetostearyl alcohol ..7g

Silikonöl IgSilicone oil Ig

Diäthylenglykolstearat 6 gDiethylene glycol stearate 6 g

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

Konservierungsmittel auf Grundlage von p-Hydroxybenzoesäurepropylester, im Handel unter dem Namen »Nipasol« 0,10 gPreservative based on propyl p-hydroxybenzoate, commercially available under the name "Nipasol" 0.10 g

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

Beispiel 13 Milch gegen Akne S-Tritylcysteaminhydrochlorid der FormelExample 13 Milk for acne S-tritylcysteamine hydrochloride of the formula

(C6H6)3 C-S-CH2-CH2-NH2, HCl,(C 6 H 6 ) 3 CS-CH 2 -CH 2 -NH 2 , HCl,

H2O 2gH 2 O 2g

Carbopol 934 0,375 gCarbopol 934 0.375 g

Iscpropylester von Wollfettsäuren IgIscpropyl 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 8 Konservierungsmittel auf Grundlage von p-Hydroxybenzoesäuremethylester, . im Handel unter dem Namen »Nipa-Triethanolamine, make up to a pH value of 8 Preservative based on p-Hydroxybenzoic acid methyl ester,. in trade under the name »Nipa-

gine« 0,10 ggine «0.10 g

Konservierungsmittel auf Grundlage von p-Hydroxybenzoesäurepropylester, im Handel unter dem Namen »Nipa-Preservative based on propyl p-hydroxybenzoate, in trade under the name »Nipa-

sol« 0,10 gsol «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 C8H5-CH2-S-CH2-CH2-NH2, HO1C-/\ IgS-benzyl cysteamine nicotinate of the formula C 8 H 5 -CH 2 -S-CH 2 -CH 2 -NH 2 , HO 1 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 Athylacetat 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.

Beispiel 16Example 16

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

S-Benzylcysteaminhydrobromid der FormelS-benzylcysteamine hydrobromide of the formula

CgH5-CH2-S-CH2-CH2-NH2, BrH 5 g Mit destilliertem parfümiertem WasserCgH 5 -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

Bei dem in diesem Haarbehandlungsmittel verwendeten S-Benzylcysteaminhydrobromid handelt es sich um aus Dichloräthan kristallisierte weiße Kristalle mitThe S-benzylcysteamine hydrobromide used in this hair treatment agent is around white crystals crystallized from dichloroethane

einem Schmelzpunkt von 130° C, die in Wasser und Alkoholen löslich sind.a melting point of 130 ° 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 167° C, die in Äthanol unlöslich, in Wasser jedoch löslich sind.The S-benzylcysteamine ditrate used in this hair treatment agent is from a mixture of water and ethanol, white nandelles crystallized with a melting point of 167 ° C, which are insoluble in ethanol but soluble in water.

Beispiel 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 Wasser auffüllen auf 100 cm3 Make up to 100 cm 3 with distilled perfumed water

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 130°C, die in Wasser und Äthanol löslich sind.The S-benzylcysteamine p-toluenesulfonate used in this hair treatment agent is around white crystals obtained by crystallization in a mixture of ethanol and ether with a Melting point from 126 to 130 ° C, which are soluble in water and ethanol.

Beispiel 20Example 20

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

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 Make up to 100 cm 3 with water

7 87 8

Bei dem in diesem Haarbehandlungsmittel verwen- verabreicht, und innerhalb von 72 Stunden wurde beiWhen used in this hair treatment agent, and within 72 hours when

deten S-Benzylcysteaminphosphat handelt es sich um keinem der Tiere der Tod festgestellt,the S-benzylcysteamine phosphate is none of the animals found to be dead,

aus einer Mischung von Wasser und Äthanol kristalli- Außerdem hat man keinerlei Reizwirkung auf derfrom a mixture of water and ethanol crystalli- In addition, there is no irritating effect on the

sierte weiße Nadeln mit einem Schmelzpunkt von naut dieser Tiere festgestellt, woraus zu schließen ist,catalyzed white needles with a melting point of n aut these animals found which suggests,

1420C, die in Äthanol unlöslich, in Wasser jedoch 5 daß die neuen kosmetischen Mittel nicht toxisch sind,142 0 C, which is insoluble in ethanol, but 5 in water that the new cosmetic agents are not toxic,

löslich sind. Die am Menschen durchgeführten Versuche habenare soluble. Have the experiments carried out on humans

Beispiel 21 bestätigt, daß die neuen kosmetischen Mittel die HautExample 21 confirms that the new cosmetic agents are the skin

nicht angreifen.do not attack.

Es wird ein Haarbehandlungsmittel mit folgender ■ Die höhere Aktivität der erfindungsgemäßen Cyste-It is a hair treatment agent with the following ■ The higher activity of the cyste according to the invention

Zusammensetzung hergestellt: 10 aminderivate, verglichen mit der von Cysteinderiva-Composition made: 10 amine derivatives, compared with that of cysteine derivative

S-Amino-S-thiapentansäure-methvlester- ten gemäß den bekanntgemachten Unterlagen desS-amino-S-thiapentanoic acid methvlester- th according to the published documents of the

hydrochlorid der Formel " belgischen Patents 6 58 449 im Tierversuch ergibthydrochloride of the formula "Belgian patent 6 58 449 results in animal experiments

CH„OOC - CH, - S - CH2 - CH2 - NH2, sich aus folgender Gegenüberstellung.CH “OOC - CH, - S - CH 2 - CH 2 - NH 2 , result from the following comparison.

HQ " !. 1,5 g Es Wu^611 folgende Verbindungen getestet: H Q "!. 1.5 g Es Wu ^ 611 the following compounds tested:

Methionin 0/75 g 15 Methionine 0/75 g 15

Mit destilliertem parfümiertem Wasser I- S-Benzylcystein-hydrochloridWith distilled perfumed water I-S-Benzylcysteine hydrochloride

auffüllen auf... 100 cm« C6H5-CH2-S-CH2-CH-COOH1HCifill up to ... 100 cm «C 6 H 5 -CH 2 -S-CH 2 -CH-COOH 1 HCi

Bei dem in diesem Haarbehandlungsmittel verwen- NH2
deten S-Amino-S-thiapentansäure-methylester-hydro- 20In the case of this hair treatment agent, NH 2
deten S-amino-S-thiapentanoic acid methyl ester-hydro-20

chlorid handelt es sich um durch Kristallisation aus n. Methyl-S-benzylcysteinat-hydrochloridchloride is obtained by crystallization from n. Methyl-S-benzylcysteinate hydrochloride

einer Mischung von Methanol und Äthylacetat erhal- C6H5- CH2- S —CH.,- CH- COOCH3 a mixture of methanol and ethyl acetate gives - C 6 H 5 - CH 2 - S - CH., - CH - COOCH 3

tene weiße Plättchen mit einem Schmelzpunkt von " |ten white platelets with a melting point of "|

1000C, die in Wasser und Äthanol löslich sind. NH2, HCl100 0 C, which are soluble in water and ethanol. NH 2 , HCl

B e i s ρ i e 1 22 HI. s. CarboxymethylcysteinB e i s ρ i e 1 22 HI. see carboxymethylcysteine

Es wird ein Haarbehandlungsmittel mit folgender HOOCCH2—S—CH2 — CH—COOHIt becomes a hair treatment agent with the following HOOCCH 2 —S — CH 2 —CH — COOH

Zusammensetzung hergestellt: IComposition made: I.

S-Amino-S-thiapentansäurebutylester- 3°S-Amino-S-thiapentanoic acid butyl ester -3 °

hydrochlorid der Formel IV. S. Benzylcysteamin-hydrochlondhydrochloride of the formula IV. S. Benzylcysteamine hydrochloride

C4H9OCO-CH2-S-CH2-CH2-NH2, C6H5-CH2-S-CH2-CH2-NH25HClC 4 H 9 OCO-CH 2 -S-CH 2 -CH 2 -NH 2 , C 6 H 5 -CH 2 -S-CH 2 -CH 2 -NH 25 HCl

HCl IgHCl Ig

Dimethylhydantoin-Formol-Harz 0,5 g v· S-CarboxymethylcysteaminDimethylhydantoin-Formol-Resin 0.5 g v · S-carboxymethylcysteamine

Dimethyldüaurylammoniumchlorid ...0,5g 35 HOOCCH2-S-CH2-CH2-Nh2.Dimethyldüaurylammoniumchlorid ... 0.5g 35 HOOCCH 2 -S-CH 2 -CH 2 -Nh 2 .

Alkohol 60^m3 Die Verbindungen I, II und III sind in der BE-PSAlcohol 60 ^ m 3 The compounds I, II and III are in the BE-PS

Mit Wasser auffüllen auf ".'.'.'.'.'.'.'.'.'.'.'. 100 cm3 6 58 449 aufgeführt, während die Verbindungen IVTop up with water to ". '.'. '.'. '.'. '.'. '.'. '. 100 cm 3 6 58 449 listed, while compounds IV

und V erfindungsgemäß in Betracht kommen.and V come into consideration according to the invention.

Das in diesem Haarbehandlungsmittel verwendete 40 Die Antiseborrhoe-Wirkung dieser 5 VerbindungenThe antiseborrhea effect of these 5 compounds used in this hair treatment agent

S-Amino-S-thiapentansäurebutylester-hydrochlorid ist wird durch biochemische Analysen gezeigt, die aufS-Amino-S-thiapentanoic acid butyl ester hydrochloride is shown by biochemical analyzes based on

bei gewöhnlicher Temperatur eine Flüssigkeit, die sich der Haut von Wistar-Ratten durchgeführt werden,at ordinary temperature a liquid that can be carried on the skin of Wistar rats,

bei O0C verfestigt und die bei 18O0C unter Zersetzung die vorher einer geeigneten Mangeldiät unterworfensolidified at O 0 C and that at 18O 0 C with decomposition which was previously subjected to a suitable deficient diet

verdampft. Sie ist in Alkohol löslich und in Wasser wurden (vgl. G. Aubin, J. Brod. G. Manoussos, Parf.evaporates. It is soluble in alcohol and in water (cf. G. Aubin, J. Brod. G. Manoussos, Parf.

wenig löslich. 45 Cosm. Sav. France, 1971, Vol. I, Nr. 8 Seite 421),sparingly soluble. 45 Cosm. Sav. France, 1971, Vol. I, No. 8 page 421),

Statt der in den vorstehenden Beispielen eingesetzten um Seborrhoe zu erzeugen.Instead of those used in the previous examples to produce seborrhea.

aktiven Komponenten kann beispielsweise auch das Wäßrige Lösungen der 5 Verbindungen (0,02 mMol S-Benzylcysteamindicilrat eingesetzt werden, bei dem in 0,5 ml Wasser) werden bei fünf Gruppen von jees sich um durch Kristallisation aus Äthanol erhaltene weils 15 Ratten während zwölf aufeinanderfolgenweiße Kristalle mit einem Schmelzpunkt von 1100C 50 den Tagen appliziert.
handelt, die in Wasser löslich sind. Für diese Applikation wird der geschorene Rük-active components, for example, the aqueous solutions of the 5 compounds (0.02 mmol of S-benzylcysteamine dicilrate in which in 0.5 ml of water) are used in five groups of 15 rats obtained by crystallization from ethanol during twelve consecutive white Crystals with a melting point of 110 ° C. applied for 50 days.
acts that are soluble in water. For this application, the shorn back is

Toxizitätsversuche mit dem erfindungsgemäßen kenbereich hinter der Schulter jeder Ratte verwen-Use toxicity tests with the kenbereich according to the invention behind the shoulder of each rat

kosmetischen Mittel wurden einerseits mit männlichen det, welcher eine Fläche von 15 cm2 aufweist. EineCosmetic agents were on the one hand with male det, which has an area of 15 cm 2 . One

Wistarratten, die ungefähr 6 Wochen alt waren und Vergleichsgruppe von 15 Ratten erhält während desWistar rats that were approximately 6 weeks old and a comparison group of 15 rats received during the

ungefähr 100 g wogen, und andererseits mit gewöhnli- 55 Versuchs nur Wasser.weighed about 100 g, and on the other hand with usual experiment only water.

chen männlichen weißen Mäusen mit einem Gewicht Nach der Behandlungsperiode werden die TiereWeighing male white mice After the treatment period, the animals are

von ungefähr 20 g durchgeführt. getötet und die Hautteile werden entnommen, damitof approximately 20 g. killed and the skin parts are removed so that

Drei Gruppen von 20 Tieren jeder Gattung wurde biochemische Analysen der Epidermis durchgeführtBiochemical analyzes of the epidermis were carried out on three groups of 20 animals of each genus

eine subkutane Injektion pro Tier von jeweils werden können.one subcutaneous injection per animal of each can be made.

60 Alle Ratten sind gleich alt und männlich. In zwei60 All rats are of the same age and male. In two

a) S-Carboxymethylcysteamin in einer Menge von Fällen (Verbindungen II und IV)^ werden auch an lg/kg für die erste Gruppe, weiblichen Ratten Versuche durchgeführt, was beia) S-carboxymethylcysteamine in a lot of cases (compounds II and IV) ^ are also at lg / kg for the first group, female rats experiments carried out what at

,,„„., . , 4 den Ergebnissen berücksichtigt ist.,, "".,. , 4 of the results is taken into account.

b) S-Tritylcysteaminhydrochlond in einer Menge vonb) S-trityl cysteamine hydrochloride in an amount of

0,5 g/kg Lebendgewicht für die zweite Gruppe, 6$ Bestimmung der Hautfette:0.5 g / kg live weight for the second group, $ 6 Determination of the skin lipids:

c) S-Benzylcysteaminhydrochlorid in einer Menge Bei jedem Tier löst man die Rückenhaut ab und von 0,15 g/kg Lebendgewicht für die dritte entnimmt mit einer Vorrichtung ein Quadrat von Gruppe 3X3 cm. Jedes Hautstütck wird mit der Epidermisc) S-Benzylcysteamine hydrochloride in an amount. The skin on the back of each animal is peeled off and of 0.15 g / kg live weight for the third takes a square of with a device Group 3X3 cm. Each piece of skin becomes with the epidermis

nach unten in eine Petrischale mit 5 ml einer Chloroform-/Methanol-Mischung gegeben. Nach Bedecken der Schale läßt man 5 Minuten einwirken und gewinnt dann das Lösungsmittel wieder. Auf diese Weise verfährt man dreimal; schließlich wird die Petrischale mit 5 ml Lösungsmittel gespült, und die verschiedenen Extrakte werden vereinigt, filtriert und dann bei Raumtemperatur zur Trockene eingeengt. Der Rückstand wird in 10 ml reinem Chloroform aufgenommen. An 0,5 ml der so hergestellten Lösung wird eine colorimetrische Bestimmung nach Charonnat (Presse Mod. 1937, 45, S. 1713) durchgeführt.down into a Petri dish with 5 ml of a chloroform / methanol mixture given. After covering the dish, it is left to act for 5 minutes and the solvent is then recovered. To this Wise one proceeds three times; Finally, the Petri dish is rinsed with 5 ml of solvent, and the various extracts are combined, filtered and then concentrated to dryness at room temperature. The residue is taken up in 10 ml of pure chloroform. On 0.5 ml of the solution thus prepared a colorimetric determination according to Charonnat (Presse Mod. 1937, 45, p. 1713) is carried out.

Die Eichkurve erhält man durch Extraktion der Hautfette und Vergleich mit der Gravimetrie.
ErgebnisseThe calibration curve is obtained by extracting the skin oils and comparing them with gravimetry.
Results

(bezogen auf den Mittelwert der bei den seborrhoeischen Tieren gemessenen Hautfette)(based on the mean value of the skin lipids measured in the seborrhoeic animals)

Hautfette (ausgedrückt in jig/cm2 Haut)Skin lipids (expressed in jig / cm 2 skin)

Ge- Vergl.- VerbindungenComp. Connections

schlecht Tierebad animals

IIII

III IVIII IV

σσ 19491949 18901890 15981598 16641664 15131513 99 12141214 11411141 929929

Verringerung des Anteils der Hautfette, ausgedrückt in %>, bezogen auf den Wert des seborrhoeischen TieresReduction in the proportion of skin lipids, expressed in%>, based on the value of the seborrhoeic animal

Geschlecht Verbindungen
I IIGender connections
I II

IIIIII

IVIV

3°/o3 ° / o

18Vo
6%18Vo
6%

15 Ve15 units

22 »/ο
230/022 »/ ο
230/0

26 %26%

Wie man aus den mit den Verbindungen IV und V, d. h. mit den Cysteaminderivaten, erhaltenen Ergebnissen feststellen kann, wird eine Verringerung der Hautfette erreicht, die deutlich höher ist als die mit den Verbindungen I bis III, d. h. den Cysteinderivaten, erzielte Hautfettverringerung.As can be seen from the compounds IV and V, i. H. with the cysteamine derivatives can determine, a reduction in skin fat is achieved that is significantly higher than that achieved with the compounds I to III, d. H. the cysteine derivatives, achieved skin fat reduction.

Bei Verbindung I beobachtet man sogar nur eine Verringerung um 3 °/o, während bei dem entsprechenden Cysteaminderivat die Verringerung 22°/o beträgt.In the case of compound I, a reduction of only 3% is observed, while in the case of the corresponding one Cysteamine derivative the reduction is 22%.

Bei Verbindung II (Verringerung 18 %) ist der Unterschied bei den männlichen Ratten weniger spürbar, jedoch bei den weiblichen Ratten viel deutlicher, da man bei Verbindung II eine Verringerung um 6 °/o und bei Verbindung IV eine Verringerung um 23% beobachtet.With compound II (decrease 18%) the difference is less noticeable in the male rats, but much more noticeable in the female rats, there a decrease of 6% for compound II and a decrease of 23% for compound IV observed.

Die bessere Aktivität der Cysteaminderivate zeigt sich auch, wenn man die Verringerung durch Verbindung III (15%) mit jener durch die entsprechende Cysteaminverbindung (Verbindung V, 26%) vergleicht. The better activity of the cysteamine derivatives can also be seen when looking at the reduction through compound III (15%) with that by the corresponding Compare cysteamine compound (Compound V, 26%).

Claims (2)

Patentansprüche:Patent claims: 1. Haarbehandlungsmittel, gekennzeichnet durch einen Gehalt an Wirkstoffen der Formel1. Hair treatment agents, characterized by a content of active ingredients formula R-S-CH2-CH2-NH2 RS-CH 2 -CH 2 -NH 2 worin R das Radikal — CH2 — C6H5, das Radikal — CH2 — COOH oder das Radikal — C(CeH5)3 bedeutet und deren Salze mit einer organischen Säure oder einer Mineralsäure sowie die Ester der eine Carboxylgruppe enthaltenden Verbindung. where R is the radical - CH 2 - C 6 H 5 , the radical - CH 2 - COOH or the radical - C (C e H 5 ) 3 and the salts thereof with an organic acid or a mineral acid and the esters of the carboxyl group-containing Link. 2. Haarbehandlungsmittel nach Anspruch 1, dadurch gekennzeichnet, daß es eine Konzentration an aktivem Wirkstoff zwischen 0,5 und 5%, vorzugsweise zwischen 1,5 und 2%, aufweist.2. Hair treatment agent according to claim 1, characterized in that it has a concentration of active ingredient between 0.5 and 5%, preferably between 1.5 and 2% . Die vorliegende Erfindung betrifft ein Haarbehandlungsmittel mit einem Gehalt an Wirkstoffen der FormelThe present invention relates to a hair treatment composition with a content of active ingredients of the formula R — S — CH2 — CH2 — NH2 R - S - CH 2 - CH 2 - NH 2 worin R das Radikal — CH2 — C6H5, das Radikal — CH2 — COOH oder das Radikal — C(CeH?)3 bedeutet. Die Konzentration an aktivem Wirkstoff in dem erfindungsgemäßen Haarbehandlungsmittel liegt zweckmäßigerweise zwischen 0,5 und 5 % und vorzugsweise zwischen 1,5 und 2%. Die Wirkstoffe in dem erfindungsgemäßen Haarbehandlungsmittel können dabei als freie Basen, sofern diese freien Basen nicht toxisch sind, oder in Form ihrer Salze mit einer organischen Säure oder einer Mineralsäure, wie Chlorwasserstoffsäure, Anwendung finden. Enthält der in den erfindungsgemäßen Haarbehandlungsmitteln eingesetzte Wirkstoff eine Carboxylgruppe, so können auch Ester davon Anwendung finden, wobei derartige veresterte Produkte eine verbesserte Lipoidlöslichkeit zeigen.where R is the radical - CH 2 - C 6 H 5 , the radical - CH 2 - COOH or the radical - C (C e H ? ) 3 . The concentration of active ingredient in the hair treatment agent according to the invention is expediently between 0.5 and 5% and preferably between 1.5 and 2%. The active ingredients in the hair treatment composition according to the invention can be used as free bases, provided these free bases are not toxic, or in the form of their salts with an organic acid or a mineral acid, such as hydrochloric acid. If the active ingredient used in the hair treatment compositions according to the invention contains a carboxyl group, esters thereof can also be used, such esterified products showing improved lipoid solubility. Zu den erfindungsgemäß einsetzbaren Wirkstoffen gehören insbesondere S-Carboxymethylcysteamin und dessen Hydrochlorid, S-Trilylcysteamin und dessen Hydrochlorid sowie S-Benzylcysteamin und dessen Hydrochlorid.The active ingredients which can be used according to the invention include, in particular, S-carboxymethylcysteamine and its hydrochloride, S-trilylcysteamine and its hydrochloride and S-benzylcysteamine and its Hydrochloride. Die erfindungsgemäßen Haarbehandlungsmittel können in Form von Lotionen, Haarwassern, als Salben, Cremes, Pomaden, Brillantinen, als Gelee, in Form einer Suspension, Dispersion oder Lösung in Wasser, Wasser-Alkohol-Mischungen oder öl oder in jeder anderen geeigneten kosmetischen Zubereitungsform vorliegen. In Frage kommen insbesondere Lösungen der erfindungsgemäß eingesetzten Wirkstoffe in Wasser oder alkoholischen Lösungen sowie Lösungen oder Dispersionen in kosmetischen ölen, Cremes oder Gelees. In allen Fällen können die erfindungsgemäßen Haarbehandlungsmittel einen oder mehrere der erfindungsgemäß eingesetzten Wirkstoffe enthalten, wobei auch weitere Stoffe vorliegen können, beispielsweise in der Kosmetik allgemein verwendete Komponenten wie Penetrationsmittel, Netzmittel, Parfüms, Farbstoffe od. dgl.The hair treatment compositions according to the invention can be in the form of lotions, hair lotions, as ointments, Creams, pomades, brillantines, as jelly, in the form of a suspension, dispersion or solution in water, Water-alcohol mixtures or oil or in any other suitable cosmetic preparation form are present. Solutions of the active ingredients used according to the invention in water are particularly suitable or alcoholic solutions as well as solutions or dispersions in cosmetic oils, creams or Jellies. In all cases, the hair treatment agents according to the invention can be one or more of the agents according to the invention Contain active ingredients used, it also possible for other substances to be present, for example Components commonly used in cosmetics such as penetrants, wetting agents, perfumes, dyes or the like Die erfindungsgemäßen Haarbehandlungsmittel besitzen ausgezeichnete kosmetische Wirksamkeit in Hinblick auf eine Herabsetzung und Beseitigung des fettigen Aussehens der Haare sowie der Beseitigung von Schuppen, unerwünschten Talgansammlungen, bedingt durch übermäßige Talgdrüsensekretion und meist von mehr oder weniger starkem Haarausfall begleitet, und ähnlichen im wesentlichen durch Seborrhoe verursachten unerwünschten und wenig ästhetischen Zuständen. Versuche mit einem erfindungsgemäßen Haarbehandlungsmittel in Form eines HaarwassersThe hair treatment compositions according to the invention have excellent cosmetic effectiveness in With a view to reducing and eliminating the greasy appearance of hair as well as eliminating Dandruff, unwanted accumulation of sebum caused by excessive sebum secretion and mostly accompanied by more or less severe hair loss, and the like mainly by seborrhea caused undesirable and unaesthetic conditions. Experiments with an inventive Hair treatment preparations in the form of a hair lotion ίο haben dabei gezeigt, daß bei Behandlung mit einem derartigen erfindungsgemäßen Haarbehandlungsmittel das fettige Aussehen der behandelten Haare vorteilhaft verbessert wird, die behandelten Haare werden weniger schnell wieder fett, und eine Wasserwelle hält in den behandelten Haaren besser.ίο have shown that when treated with a Such hair treatment compositions according to the invention, the greasy appearance of the treated hair is advantageous is improved, the treated hair becomes greasy again less quickly, and a water wave lasts better in the treated hair. Es ist bereits die Verwendung von synthetischen Verbindungen auf Schwefelbasis als kosmetische Mittel gegenüber fettem Haar vorgeschlagen worden, die Mehrzahl der bisher zu diesem Zweck verwendeten Stoffe befriedigen jedoch nicht in allen Fällen und sind im allgemeinen nicht für die erforderliche Zeit beständig. There is already the use of synthetic sulfur-based compounds as cosmetic Agents proposed against oily hair, the majority of those heretofore used for this purpose However, substances are not satisfactory in all cases and are generally not stable for the required time. Die erfindungsgemäß eingesetzten Wirkstoffe be- , sitzen gegenüber den bisher bekannten Produkten den Vorteil, daß sie in Wasser oder einige davon in einer 50%igen alkoholischen Lösung löslich sind.The active ingredients used according to the invention have, compared to the previously known products Advantage that they are soluble in water or some of them in a 50% alcoholic solution. Die erfindungsgemäßen Haarbehandlungsmittel haben auch die vorteilhafte Eigenschaft, Haarausfall zu verhindern.The hair treatment compositions according to the invention also have the advantageous property of preventing hair loss impede. Zur Anwendung werden die erfindungsgemäßen Haarbehandlungsmittel auf die Kopfhaut aufgebracht. Die nachfolgenden Beispiele erläutern die Erfindung. For use, the hair treatment compositions according to the invention are applied to the scalp. The following examples illustrate the invention. Beispiel 1example 1 Haarbehandlungsmittel
InIOO ecm destilliertem parfümiertem Wasser sind 1,5 g S-Carboxymethyl-cysteamin der FormelHair treatment preparations
In 100 ecm of distilled perfumed water there are 1.5 g of S-carboxymethyl-cysteamine of the formula HOOC -CH2-S-CH0-CH2-NH,HOOC -CH 2 -S-CH 0 -CH 2 -NH,
DE19661617704 1965-12-22 1966-12-20 Hair treatment preparations Expired DE1617704C3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
LU50125A LU50125A1 (en) 1965-12-22 1965-12-22

Publications (3)

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DE1617704A1 DE1617704A1 (en) 1972-04-06
DE1617704B2 DE1617704B2 (en) 1975-03-20
DE1617704C3 true DE1617704C3 (en) 1980-09-25

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Family Applications (1)

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DE19661617704 Expired DE1617704C3 (en) 1965-12-22 1966-12-20 Hair treatment preparations

Country Status (11)

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JP (1) JPS5335922B1 (en)
AT (1) AT282066B (en)
AU (1) AU418744B1 (en)
BE (1) BE691589A (en)
CH (2) CH468187A (en)
DE (1) DE1617704C3 (en)
FR (2) FR1505874A (en)
GB (1) GB1161349A (en)
IT (1) IT975504B (en)
LU (1) LU50125A1 (en)
NL (2) NL6618039A (en)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
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
US4388475A (en) 1979-08-15 1983-06-14 Merck & Co., Inc. Allylsulfoxide 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

Also Published As

Publication number Publication date
DE1617704B2 (en) 1975-03-20
LU50125A1 (en) 1967-06-22
CH474494A (en) 1969-06-30
DE1617704A1 (en) 1972-04-06
FR6936M (en) 1969-05-12
NL131093C (en)
JPS5335922B1 (en) 1978-09-29
AU418744B1 (en) 1968-06-27
GB1161349A (en) 1969-08-13
CH468187A (en) 1969-02-15
BE691589A (en) 1967-06-21
AT282066B (en) 1970-06-10
IT975504B (en) 1974-08-10
FR1505874A (en) 1967-12-15
NL6618039A (en) 1967-06-23

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