US3534032A - N - tertiaryaminoalkyl - n - aliphaticalpha aliphatic aminosuccinamic acid amides and corresponding maleamic acid intermediates therefor - Google Patents

N - tertiaryaminoalkyl - n - aliphaticalpha aliphatic aminosuccinamic acid amides and corresponding maleamic acid intermediates therefor Download PDF

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US3534032A
US3534032A US424846A US3534032DA US3534032A US 3534032 A US3534032 A US 3534032A US 424846 A US424846 A US 424846A US 3534032D A US3534032D A US 3534032DA US 3534032 A US3534032 A US 3534032A
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alkyl
dodecyl
aliphatic
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aliphaticalpha
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Gregoire Kalopissis
Andre Viout
Guy Vanlerberghe
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LOreal SA
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    • 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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Abstract

Surface active compositions which contain a surface-active compound having the formula IN WHICH R and R' are an alkyl or alkenyl group which has 10-18 carbon atoms, R1 and R2 are lower alkyl or with the N atom a morpholino group and n is 2-5.

Description

United States Patent Int. Cl. 067d 87/42 US. Cl. 260-2471 9 Claims ABSTRACT OF THE DISCLOSURE 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. A process of thickening acid aqueous solutions.
This invention relates to new asparagine derivatives having surface-active properties, to a process for their preparation and to hair treatment compositions containing them.
We have now found that certain related asparagine derivatives not only show surface activity, but possess other properties which are of considerable interest in relation to the treatment of hair.
The asparagine derivatives of the invention are compounds of the formula:
I CH2CO-N-(OHz)nN RNH( )HC 0 011 R2 (1) where 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.
Moreover, in acidic aqueous solutions these compounds show a very pronounced thickening and gelling effect. Since products currently employed as thickeners or gelling agents generally do not possess in themselves any deter- 3,534,032 Patented Oct. 13, 1970 gent or hair treating property, it will be seen that compounds of the invention are particularly advantageous, and because of this combination of properties they have a very Wide range of use, for example, in aqueous solu tions of other surface-active substances, especially those of cationic or non-ionic character, and in aqueous solutions of dyes.
The compounds of the invention can be prepared by a process which comprises condensing maleic anhydride with an alkylene diamine of the formula:
i NH-(OH2)nN where R, R and R and n have the meanings given above, satisfying the reaction product to obtain the corresponding sodium, potassium or ammonium salt, and reacting said salt with a primary fatty amine of the formula: RNH where R has the meaning given above.
Particularly appropriate 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. It has been found that excellent results have been obtained using as primary amine a mixture of fatty amines derived from copra acid or tallow acid, which yield a mixture of compounds of Formula 1 diflering only in the value of the substituent R, the various R substituents being the various alkyl radicals present in tallow or copra acids respectively.
The invention is illustrated by the following examples.
EXAMPLE I Preparation of the sodium salt of N -[alkyl(tallow)]-N- (dodecyl) -N- (N,N'-diethylaminoethyl) asparagine (1) Preparation of N',N'-diethyl-N-dodecyl-ethylenediamine.There are mixed with stirring 2 moles of dodecyl bromide and 10 moles of N,N'-diethylethylenediamine (96.6%) the temperature being maintained below 50 C. At the end of several hours, the reaction is complete. There are then added 4.3 moles of potassium hydroxide in pellet form, with vigorous stirring. The excess of potassium hydroxide and the potassium bromide formed are separated by filtration. The excess of N,N'-diethylethylenediamine is thereafter evaporated under reduced pressure, and the crude product thus obtained is washed with Water and dried in vacuo on the water bath.
N',N'-diethyl-N-dodecyl-ethylenediamine is thus isolated in an almost quantitative yield and in a purity of 98%.
(2) Preparation of N-dodecyl-N-(N,N-diethylaminoethyl) maleamie acid.One mole of N,N-diethyl-N- dodecyl-ethylenediamine is dissolved in 300 ml. of ethyl acetate.
To this solution is added with stirring, in an hour and a half, one mole of maleic anhydride in solution in 300 ml. of ethyl acetate, the temperature being maintained between 35 and 40 C. The solid which precipitates is separated, washed with ethyl acetate and dried in vacuo, and N-dodecyl-N,N'-diethylaminoethyl)maleamic acid is isolated as a white, water-soluble powder in a yield of (3) Addition of the primary amine derived from tallow fatty acids.0.7 mole of N-dodecyl-N-(N,N'-diethylaminoethyl) maleamic acid is dissolved in 300 ml. of ethyl alcohol, and the solution is neutralised with a calculated qlantity of concentrated aqueous sodium hydroxide solution.
There is then added 0.7 mole of a mixture of primary amines derived from tallow fatty acids, and the mixture is heated at 65 C., for 11 hours. After evaporation of the alcohol, the product obtained takes the form of an oil dispersible in water, which contains 4% of unreacted primary amine.
EXAMPLE II Preparation of the sodium salt of N -[alkyl(copra)]-N- (cetyl) -N- (N,N'-diethylaminoethyl asparagine By proceeding in an analogous to Example I, N-cetyl- N-(N,N'-diethylaminoethyl)maleamic acid is obtained from N,N'-diethyl-N-cetyl-ethylenediamine and maleic anhydride. The desired product is obtained by the addition to the soduim salt of the maleamic acid of a mixture of primary amines derived from copra fatty acids in an analogous way to Example 1.
EXAMPLE III Preparation of the sodilm salt of N -[alkyl(tallow)]-N- cetyl -N- (N ',N'-diethylaminoethyl) asparagine By the process analogous to that described in Example I, this product is obtained by the addition of a mixture of primary amines derived from tallow fatty acids to sodium N-cetyl-N-(N,N'-dethylaminoethyl)maleamate.
EXAMPLE IV Preparation of the sodium salt of N -[alkyl(copra)]-N- (dodecyl -N- (N',N'-diethylaminoethyl) asparagine This product is obtained by reacting the mixture of primary amines derived from copra fatty acids with sodium N-dodecyl-N- (N',N'-diethylaminoethyl)maleamate in a process analogous to that described in Example 1.
EXAMPLE V Preparation of the sodium salt of N -[a1kyl(tallow)]-N- (dodecyl) -N-(morpholinoethy1) asparagine By a process analogous to that described in Example I, there is obtained from dodecyl bromide and aminoethylmorpholine, {3-(dodecylamino)ethylmorpholine.
The condensation of this diamine with maleic anhydride gives the corresponding maleamic acid whch, after neutralsation with sodium hydroxide, is reacted with the mixture of primary amines derived from tallow fatty acids yielding the desired product in the form of an oil.
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.
EXAMPLE VII Preparation of the sodium salt of N [alkyl(copra)]-N- (cetyl)-N(N,N'-diethylaminopropyl)asparagine This product is obtained by a process analogous to that described in Example VI. It takes the form of a viscous oil.
Examples VII I to XVI below illustrate the use of compounds of the invention.
EXAMPLE VIII The following mixture is prepared:
Sodium salt of N -[alkyl(tal1ow)]-N-dodecyl)-N- (N',
N'-diethylaminoethyl)asparagine--3 g.
Lactic acid, q.s. for pH 5.5
Water q.s. for 100 cc.
A transparent jelly is obtained.
4 EXAMPLE 1x In the same Way, by mixing.
Sodium salt of N -[alkyl(tallow)]-N-(cetyl)-N-(N,N'-
diethylaminoethyl)asparagine-3 g.
Lactic acid, q.s. for pH 4.
Water, q.s. for cc.
a translucent gel is obtained.
EXAMPLE X There is prepared an aqueous solution containing:
The condensate obtained from 1 mole of tridecyl alcohol and 15 moles of ethylene oxide7 g.
Diethanolamide of copra fatty acids3 g.
Sodium salt of N -[alkyl(tallow)]-N-(dodecyl)-N-(N,
N'-diethylaminoethyl)asparagine6 =g.
Lactic acid, q.s. for pH 5.
Water, q.s. for 100 cc.
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.
EXAMPLE XI There is prepared a solution containing:
The condensate obtained from 1 mole of copra fatty alcohol and 12 moles of ethylene oxide8 g.
Diethanolamide of copra fatty acids-4 g.
Sodium salt of N -[alkyl(copra)]-N-(N,N-diethylan1- inopropyl)asparagine-3 g.
Sodium salt of N -[alkyl(tallow)]-N-(dodecyl)-N-(N,
N'-diethylaminoethyl)asparagine6 g.
Lactic acid, q.s. for pH 5.
Water, q.s. for 100 cc.
There is thus obtained a shampoo of viscous consistency which imparts suppleness to hair and makes it easy to comb. Moreover, the hair after having been washed with this shampoo does not exhibit any accumulation of electrostatic charge. The viscosity of this shampoo is clearly higher than that obtained in the absence of the compound according to the present application.
EXAMPLE XII There is prepared a solution containing:
The condensate of 1 mole of octylphenol and 18 moles of ethylene oxide7 g.
Diethanolamide of copra fatty acids-4 g.
Cetyltrimethylammonium bromide-2 g.
Sodium salt of N -[alkyl(tal1oW)]-N-(cetyl)-N-(N',N'-
diethylaminoethyl) asparagine-6 g.
Lactic acid, q.s. for pH 5.
Water, q.s. for 100 cc.
A thick solution is obtained. 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.
EXAMPLE XIV There is prepared by conventional procedure a cream containing:
Sodium salt of N -[alkyl(tallow)]-N-(cetyl-N-(N,N'-
diethylaminoethyl)asparagine g.
Cetyl alcohol3 g.
The condensate of 1 mole of stearyl alcohol and moles of ethylene oxide3 g.
Water70 cc.
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.
From 5 to 10 g. of this cream are applied to hair sensitised by a decoloration, which is massaged for several minutes and then rinsed. The hair thus acquires softness and a gloss and is easy to comb.
EXAMPLE XV The following mixture is prepared:
Sodium salt of N -[alkyl(tallow)]-N-(dodecyl)-N- (N',
N'-diethylaminoethyl)asparagine5 g.
Picramic acid-0.5 g.
Lactic acid, q.s. for pH 6.5
Water, q.s. for 100 cc.
There is thus obtained a thick dyeing solution which when applied to the hair, imparts a glistening effect thereto, softens it and makes it easy to comb.
EXAMPLE XVI The following mixture is prepared:
There is thus obtained a viscous dyeing solution which, when applied to the hair, besides dyeing it, imparts to it a gloss and suppleness.
The mixtures of primary amines used in Examples I to VII are all being used commercially.
6 What we claim is: 1. A compound selected from the group consisting of and its sodium, potassium and ammonium salts, where R and R are selected from the group consisting of aliphatic alkyl having 10 to 18 carbon atoms and aliphatic alkenyl having 10 to 18 carbon atoms;
R and R are lower alkyl or together with the nitrogen atom on which they are attached constitute saturated monocyclic heterocyclic;
and n is an integer of 2 to 5.
2. A compound of claim 1, in which R and R are alkyl of 1-4 carbon atoms.
3. A compound of claim 1, in which R and R are methyl or ethyl.
4. A compound of claim 1, in which R and R are identical.
5. A maleamic acid derivative of the formula:
where R, R R and n have the meanings given in claim 1.
6. A compound of claim 1, wherein R and R are both alkyl.
7. A compound of claim 1, wherein R and R are both alkenyl.
8. A compound of claim 1, wherein n is 2 to 3.
9. A salt selected from the group consisting of the sodium, potassium and ammonium salts of the compound of claim 5.
References Cited UNITED STATES PATENTS 2,821,521 1/1958 Price 260-534 X FOREIGN PATENTS 1,146,332 5/1957 France.
1,344,212 10/1963 France.
NICHOLAS Si. RIZZO, Primary Examiner J. TOVAR, Assistant Examiner
US424846A 1964-01-17 1965-01-11 N - tertiaryaminoalkyl - n - aliphaticalpha aliphatic aminosuccinamic acid amides and corresponding maleamic acid intermediates therefor Expired - Lifetime US3534032A (en)

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FR960742A FR1397231A (en) 1964-01-17 1964-01-17 New surfactants and their applications
US42484665A 1965-01-11 1965-01-11
US012477A US3873688A (en) 1964-01-17 1970-02-12 Surface active compositions containing asparagine derivatives
US286698A US3891385A (en) 1964-01-17 1972-09-06 Hair softening dye compositions containing surface-active asparagine derivatives

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3891385A (en) * 1964-01-17 1975-06-24 Oreal Hair softening dye compositions containing surface-active asparagine derivatives
US4020155A (en) * 1965-09-06 1977-04-26 Societe Anonyme Dite: L'oreal Surface active agents
US4133772A (en) * 1977-05-23 1979-01-09 Kewanee Industries, Inc. Aqueous detergent compositions containing amphoteric surfactants having anti-microbial and preservative properties
US4216238A (en) * 1979-02-13 1980-08-05 Stauffer Chemical Company Dialkyl amino ethyl amides, their salts and their use as anti-ripening agents
US4258063A (en) * 1978-06-23 1981-03-24 Henkel Corporation Self-emulsifying cosmetic base
US4652585A (en) * 1984-03-24 1987-03-24 Henkel Kommanditgesellschaft Auf Aktien N-substituted diaminopropane/glutamic acid reaction products
US4837012A (en) * 1987-06-19 1989-06-06 S. C. Johnson & Son, Inc. Hair reviver composition containing film-forming amino acids
US5900213A (en) * 1993-04-28 1999-05-04 Alcon Laboratories, Inc. Use of diamines to disinfect and clean contact lenses and preserve ophthalmic compositions

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3969087A (en) * 1974-08-07 1976-07-13 Ajinomoto Co., Ltd. Gels of nonpolar liquids with N-acyl amino acids and derivatives thereof as gelling agents
FR2289179A1 (en) * 1974-10-28 1976-05-28 Morelle Jean METAL SALTS OF LIPOAMINOACIDS
US4096243A (en) * 1976-02-09 1978-06-20 Clairol Incorporated Composition for lightening hair containing an oxidizing agent and certain quaternary amines
US4532127A (en) * 1976-02-09 1985-07-30 Clairol Incorporated Composition for lightening or coloring hair containing an oxidizing agent and certain quaternary amines
US4402700A (en) * 1976-02-09 1983-09-06 Clairol Incorporated Composition for coloring hair containing an oxidizing agent and certain quaternary amines
US4440665A (en) * 1978-05-26 1984-04-03 Albright & Wilson Limited Concentrated aqueous surfactant compositions
JPS5920718B2 (en) * 1980-11-27 1984-05-15 花王株式会社 hypoallergenic cleaning agent
US4755623A (en) * 1983-09-06 1988-07-05 American Cyanamid Company Polyfunctional amine crosslinker, process for making same, and compositions containing same
DE3347534A1 (en) * 1983-12-30 1985-07-11 Hoechst Ag, 6230 Frankfurt NEW AMPHOTERIC COMPOUNDS, MIXTURES CONTAINING THESE COMPOUNDS FOR DISINFECTING CLEANING, AND METHODS FOR PRODUCING THESE COMPOUNDS AND MIXTURES
FR2745178A1 (en) * 1996-02-26 1997-08-29 Rhone Poulenc Chimie COSMETIC COMPOSITION FOR HAIR COLORING AND METHODS OF PREPARATION
FR2745176A1 (en) * 1996-02-26 1997-08-29 Rhone Poulenc Chimie Cosmetic composition for skin and hair care
DE19835327A1 (en) * 1998-08-05 2000-02-10 Henkel Kgaa Hair treatment products
US6547833B2 (en) 2001-02-23 2003-04-15 Clairol Incorporated Two-part aqueous composition for oxidative coloration of hair
US20030005526A1 (en) * 2001-05-15 2003-01-09 Stephen Casperson Two-part aqueous composition for oxidative coloration of hair
TWI450052B (en) * 2008-06-24 2014-08-21 Dynaloy Llc Stripper solutions effective for back-end-of-line operations

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US2821521A (en) * 1954-08-25 1958-01-28 American Cyanamid Co Polymers of n-(dialkylaminopropyl) maleamic acid
FR1344212A (en) * 1962-02-15 1963-11-29 Oreal New amphoteric surfactants and their preparation process

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US3891385A (en) * 1964-01-17 1975-06-24 Oreal Hair softening dye compositions containing surface-active asparagine derivatives
US4020155A (en) * 1965-09-06 1977-04-26 Societe Anonyme Dite: L'oreal Surface active agents
US4133772A (en) * 1977-05-23 1979-01-09 Kewanee Industries, Inc. Aqueous detergent compositions containing amphoteric surfactants having anti-microbial and preservative properties
US4258063A (en) * 1978-06-23 1981-03-24 Henkel Corporation Self-emulsifying cosmetic base
US4216238A (en) * 1979-02-13 1980-08-05 Stauffer Chemical Company Dialkyl amino ethyl amides, their salts and their use as anti-ripening agents
US4652585A (en) * 1984-03-24 1987-03-24 Henkel Kommanditgesellschaft Auf Aktien N-substituted diaminopropane/glutamic acid reaction products
US4837012A (en) * 1987-06-19 1989-06-06 S. C. Johnson & Son, Inc. Hair reviver composition containing film-forming amino acids
US5900213A (en) * 1993-04-28 1999-05-04 Alcon Laboratories, Inc. Use of diamines to disinfect and clean contact lenses and preserve ophthalmic compositions

Also Published As

Publication number Publication date
NL123441C (en)
FR1397231A (en) 1965-04-30
GB1058332A (en) 1967-02-08
DE1518075A1 (en) 1969-10-09
BE658288A (en) 1965-07-14
CH433374A (en) 1967-04-15
CH437644A (en) 1967-06-15
NL6500541A (en) 1965-07-19
GB1058331A (en) 1967-02-08
US3873688A (en) 1975-03-25
US3891385A (en) 1975-06-24

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