Classifications

• • 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
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
• • 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
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/41—Amines
  • A61K8/418—Amines containing nitro groups
• • 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
  • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
  • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
  • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
  • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
  • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
  • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
  • C11D1/02—Anionic compounds
  • C11D1/04—Carboxylic acids or salts thereof
  • C11D1/10—Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates thereof
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
  • Y10S8/908—Anionic emulsifiers for dyeing

Definitions

• a surface active compound selected from the group consisting of l CH2-C ON--(CH2)n-N R-NH-CH-COOH R2 and its sodium, potassium and ammonium salts, where R and R are selected from the group consisting of aliphatic alkyl having to 18 carbon atoms and aliphatic alkenyl having 10 to 18 carbon atoms;
• R and R are a lower alkyl or together with the nitrogen atom on which they are attached constitute a saturated monocyclic heterocyclic group; and n is an integer of 2 to 5.
• Shampoo, hair dye and detergent composition containing these compounds A process of conditioning and softening hair.
• This invention relates to new asparagine derivatives having surface-active properties, to a process for their preparation and to hair treatment compositions containing them.
• the asparagine derivatives of the invention are compounds of the formula:
• R and R are each an aliphatic hydrocarbon radical of 10-18 carbon atoms which can be the same or different; R and R are each a lower alkyl radical, which can be the same or diflerent, or together with the nitrogen atom to which they are attached constitute a heterocyclic residue and n is an integer of 2-5 inclusive (especially 2 or 3), and sodium, potassium and acid addition salt thereof.
• Preferred compounds are those in which R and R are alkyl radicals of 1-4 carbon atoms, for instance methyl or ethyl radicals.
• Other preferred compounds are those in which R v and R together 'with the nitrogen atom to which they are attached, constitute a saturated monocyclic heterocyclic residue, for instance a morpholino or piperidino radical.
• Compounds of the invention possess not only remarkable detergent properties, but also good softening and conditioning properties for the hair. Thus they can be used to advantage in hair shampoo or hair dyeing compositions.
• the compounds of the invention can be prepared by a process which comprises condensing maleic anhydride with an alkylene diamine of the formula:
• alkylene diamines are, for example, N-dodecyl-N',N'-diethylethy1enediamine, N-cetyl- N,N-diethylethylenediamine, N-dodecy1-N',N'-diethyltri methylenediarnine, and fl-(dodecylamino)ethylmorpholine.
• Particularly appropriate fatty amines are, for example, decylamine and dodecyl amine.
• N',N'-diethyl-N-dodecyl-ethylenediamine is thus isolated in an almost quantitative yield and in a purity of 98%.
• EXAMPLE VI Preparation of the potassium salt of N -[alkyl(ta1loW) N-(dodecyl)-N(N',N'-diethylaminopropyl)asparagine N',N'-diethyl-N-dodecyl-trimethylenediamine is first prepared by a process analogous to that described in Example I. Maleic anhydride is reacted with this diamine in solution in t-butyl alcohol. The maleamic acd thus formed is neltralised by an aqueous potassium hydroxide solution, and the potassium salt is reacted with the mixture of primary amines derived from the fatty acids of tallow. By evaporation of the solvent, the desired product is obtained in the form of a viscous oil.
• Lactic acid q.s. for pH 5.5
• a transparent jelly is obtained.
• Lactic acid q.s. for pH 4.
• N'-diethylaminoethyl)asparagine6 g.
• Lactic acid q.s. for pH 5.
• This solution is of oily consistency and when used as a shampoo imparts suppleness to the hair and makes it easy to comb.
• the viscosity of this shampoo is substantially higher than that obtained by replacing the compolnd of the invention with a cationic product in current use.
• N'-diethylaminoethyl)asparagine6 g N'-diethylaminoethyl)asparagine6 g.
• Lactic acid q.s. for pH 5.
• Lactic acid q.s. for pH 5.
• This product constitutes a shampoo which renders the hair very soft and makes it easy to comb.
• EXAMPLE XIII There are prepared (a) and (b) are mixed at about 40 C. and make up to 100 c. with water. There is thus obtained a creamy fixative, of which 100 cc. diluted with 150 cc. of hot water are used to neutralise a permanent wave.
• the mixture is allowed to cool to 40 C. and acidified by the addition of citric acid until a pH of 4 is reached, whereafter it is made up to 100 cc. with water.
• Lactic acid q.s. for pH 6.5
• R and R are lower alkyl or together with the nitrogen atom on which they are attached constitute saturated monocyclic heterocyclic;
• n is an integer of 2 to 5.
• R and R are alkyl of 1-4 carbon atoms.
• R, R R and n have the meanings given in claim 1.

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• Life Sciences & Earth Sciences (AREA)
• Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Organic Chemistry (AREA)
• Animal Behavior & Ethology (AREA)
• General Health & Medical Sciences (AREA)
• Public Health (AREA)
• Veterinary Medicine (AREA)
• Birds (AREA)
• Epidemiology (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Wood Science & Technology (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Engineering & Computer Science (AREA)
• Cosmetics (AREA)
• Pyrrole Compounds (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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Citations (3)

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• 0
  • NL NL123441D patent/NL123441C/xx active
• 1964
  • 1964-01-17 FR FR960742A patent/FR1397231A/fr not_active Expired
• 1965
  • 1965-01-11 US US424846A patent/US3534032A/en not_active Expired - Lifetime
  • 1965-01-13 CH CH47465A patent/CH437644A/fr unknown
  • 1965-01-13 CH CH121667A patent/CH433374A/fr unknown
  • 1965-01-14 BE BE658288D patent/BE658288A/xx unknown
  • 1965-01-15 DE DE19651518075 patent/DE1518075A1/de active Pending
  • 1965-01-15 GB GB40464/66A patent/GB1058332A/en not_active Expired
  • 1965-01-15 NL NL6500541A patent/NL6500541A/xx unknown
  • 1965-01-15 GB GB1993/65A patent/GB1058331A/en not_active Expired
• 1970
  • 1970-02-12 US US012477A patent/US3873688A/en not_active Expired - Lifetime
• 1972
  • 1972-09-06 US US286698A patent/US3891385A/en not_active Expired - Lifetime

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