US3337548A - N'-acyl-n'-hydrocarbon-n-tertiary aminoloweralkyl-asparagines - Google Patents

N'-acyl-n'-hydrocarbon-n-tertiary aminoloweralkyl-asparagines Download PDF

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Publication number
US3337548A
US3337548A US347397A US34739764A US3337548A US 3337548 A US3337548 A US 3337548A US 347397 A US347397 A US 347397A US 34739764 A US34739764 A US 34739764A US 3337548 A US3337548 A US 3337548A
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United States
Prior art keywords
alkyl
copra
fatty acids
formula
derived
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Expired - Lifetime
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US347397A
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English (en)
Inventor
Kalopissis Gregoire
Viout Andre
Vanlerberghe Guy
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LOreal SA
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LOreal SA
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Priority to US611485A priority Critical patent/US3379646A/en
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Publication of US3337548A publication Critical patent/US3337548A/en
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    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/20—Macromolecular organic compounds
    • D21H17/21—Macromolecular organic compounds of natural origin; 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
    • A61K8/44—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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • 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
    • C11D1/88—Ampholytes; Electroneutral compounds

Definitions

  • the compounds of the present invention are compounds of the formula:
  • the process for the preparation of the new compounds according to the invention consists in condensing maleic anhydride with the asparagine derivatives, described in the aforesaid application, of the Formula I, and thereafter adding a fatty amine of formula RNH to the double bond of the resultant product.
  • fatty amines there may be mentioned: decylamine and dodecylamine, and also the amines derived from the fatty acids of copra and tallow.
  • the invention includes within its scope washing and cleaning compositions, in particular shampoos having a pH of from 3 to 8 which contains one or more compounds of the Formula II.
  • compositions may be in the form of aqueous solutions and their pH may be acid, neutral or alkaline.
  • the compounds of Formula II function either as cationic or anionic agents, depending upon the pH.
  • numbers 1 to 6 may be followed by l to 5 crosses in accordance with the intensity of the action; since the corneal lesions are of two types, the numbers corresponding to the strongest action may also be followed by (a),
  • the cornea may be attacked in cases 5 and 6 either by the determine the point of amine employed, owing to the fact that the final product contains only 24% thereof.
  • the new compounds may be employed in various fields and notably in the cosmetic field. As already stated, they may be employed With advantage for thickening hair washing compositions.
  • R and R represent alkyl residues derived from -'the fatty acids of tallow.
  • Example 1 The procedure of Example 1 is followed, but the amines derived from the fatty acids of tallow are employed instead of copra amines.
  • the desired product is obtained in the form of a solid mass.
  • R is an alkyl residue derived from the fatty acids of tallow.
  • the product obtained takes the form of a solid mass which can be reduced to flakes by crushing.
  • CH OHrCONH(CHz)a-N R3NGH-COON-a O-CHz-CHCOONa represent the alkyl residues derived in which R and R from the fatty acids of copra.
  • arnines derived from the fatty acids of tallow are em- ,ployed instead of copra fatty amines. After evaporation of the water and the alcohol, the desired product is obtained in solid form. It can be reduced to flakes by grinding.
  • Example 6 of N (alkyl, aspar- 7 in which R, and R represent alkyl residues derived from the fatty acids of copra.
  • Example 8 There is prepared an aqueous solution containing:
  • Fatty alcohol c -c condensed with 12 mol. of ethylene oxide 12 g. Disodium salt of N -[alkyl(copra)aspartyl]- N [alkyl(copra)] N (N',N diethylaminopropyl)asparagine 6 g. Lactic acid to pH 5. Water to 100 cc.
  • An oily shampoo is obtained which leaves the hair soft and silky. In addition, no accumulation of electricity occurs on the hair.
  • This shampoo which is of oily appearance, makes the hair easy to comb and renders it soft and silky.
  • Example 12 There are mixed: Lauryl alcohol condensed with 15 mol. of ethylene oxide 8 g. Diethanolamide of copra fatty acids 2 g. Disodium salt of N [a1kyl(c0pra) aspartyl] N -[alkyl(copra)] N (N,N dimethylaminopropyl)asparagine 5 g. Lactic acid to pH 8. Water to 100 cc. This shampoo, which has an oily consistency, leaves the hair soft and supple. It exhibits no accumulation of electrostatic charges after drying.
  • Sulphate of C C alcohols and of ammonium (expressed as active constituents) 9 g.
  • This shampoo imparts softness to the hair and avoids the accumulation of electrostatic charges.
  • R1I TRz is selected from the group consisting of dilower alkylamino, morpholino or piperidino, wherein n is 2 to 5, and at least one of R and R are alkyl radicals of 10 to 18 carbon atoms.
  • R and R are alkyl radicals derived from copra fatty acids.
  • R and R are alkyl radicals derived from tallow fatty acids.
  • a compound of the formula OzHs OHZ C ONH (clam-N RaNCHCOONa -OHa-0H-000Na in which R and R are alkyl radicals derived from copra.
  • R and R are alkyl radicals derived from tallow.
  • a compound of the formula CzH5 0H,0 O-NH (emu-N R3NOH-C 0 ONa 02m in which R and R are alkyl radicals derived from tallow.
  • a compound of the formula acid and R is an alkyl radical derived from copra fatty acid.
  • R and R are alkyl radicals derived from copra fatty acid.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Organic Chemistry (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Cosmetics (AREA)
US347397A 1963-03-01 1964-02-26 N'-acyl-n'-hydrocarbon-n-tertiary aminoloweralkyl-asparagines Expired - Lifetime US3337548A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US611485A US3379646A (en) 1963-03-01 1966-10-03 Surface-active agents,process for their preparation and their use

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR926440A FR1419574A (fr) 1963-03-01 1963-03-01 Nouveaux agents tensio-actifs, leur procédé de préparation et leur application

Publications (1)

Publication Number Publication Date
US3337548A true US3337548A (en) 1967-08-22

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US347397A Expired - Lifetime US3337548A (en) 1963-03-01 1964-02-26 N'-acyl-n'-hydrocarbon-n-tertiary aminoloweralkyl-asparagines

Country Status (5)

Country Link
US (1) US3337548A (de)
AT (2) AT241431B (de)
DE (1) DE1492067B2 (de)
FR (1) FR1419574A (de)
NL (2) NL6401853A (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4154937A (en) * 1977-02-11 1979-05-15 E. R. Squibb & Sons, Inc. Hydroxycarbamoylalkylacylpipecolic acid compounds

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2821521A (en) * 1954-08-25 1958-01-28 American Cyanamid Co Polymers of n-(dialkylaminopropyl) maleamic acid
US3158535A (en) * 1961-10-02 1964-11-24 Exxon Research Engineering Co Pyrethrin-elastomer insecticidal composition and method

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2821521A (en) * 1954-08-25 1958-01-28 American Cyanamid Co Polymers of n-(dialkylaminopropyl) maleamic acid
US3158535A (en) * 1961-10-02 1964-11-24 Exxon Research Engineering Co Pyrethrin-elastomer insecticidal composition and method

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4154937A (en) * 1977-02-11 1979-05-15 E. R. Squibb & Sons, Inc. Hydroxycarbamoylalkylacylpipecolic acid compounds

Also Published As

Publication number Publication date
AT241431B (de) 1965-07-26
DE1492067B2 (de) 1977-04-21
DE1492067A1 (de) 1969-06-26
FR1419574A (fr) 1965-12-03
NL125248C (de)
AT249877B (de) 1966-10-10
NL6401853A (de) 1965-04-26

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