US3873688A - Surface active compositions containing asparagine derivatives - Google Patents

Surface active compositions containing asparagine derivatives Download PDF

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US3873688A
US3873688A US012477A US1247770A US3873688A US 3873688 A US3873688 A US 3873688A US 012477 A US012477 A US 012477A US 1247770 A US1247770 A US 1247770A US 3873688 A US3873688 A US 3873688A
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composition
hair
asparagine
surface active
alkyl
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US012477A
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Gregoire Kalopissis
Andre Viout
Guy Vanlerberghe
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LOreal SA
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LOreal SA
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Priority to NL123441D priority Critical patent/NL123441C/xx
Priority to FR960742A priority patent/FR1397231A/en
Priority to US424846A priority patent/US3534032A/en
Priority to CH121667A priority patent/CH433374A/en
Priority to CH47465A priority patent/CH437644A/en
Priority to BE658288D priority patent/BE658288A/xx
Priority to NL6500541A priority patent/NL6500541A/xx
Priority to GB1993/65A priority patent/GB1058331A/en
Priority to GB40464/66A priority patent/GB1058332A/en
Priority to DE19651518075 priority patent/DE1518075A1/en
Application filed by LOreal SA filed Critical LOreal SA
Priority to US012477A priority patent/US3873688A/en
Priority to US286698A priority patent/US3891385A/en
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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

  • ABSTRACT Surface active compositions which contain a surfaceactive compound having the formula R-NH-CH-COOH 2 in which R and R are an alkyl or alkenyl group which has 10-18 carbon atoms, R and R are lower alkyl Or with the N atom a morpholino group and n is 25.
  • This invention relates to cosmetic compositions which contain new asparagine derivatives having surface-active properties, and to hair treating compsitions containing them.
  • the asparagine derivatives used in the compositions of this invention are compounds having the formula:
  • R and R are each an alkyl or alkenyl group which has -18 carbon atoms which can be the same or different; R, and R are each lower alkyl, which can be the same or different, or together with the nitrogen atom to which they are attached constitute a morpholino residue and n is an integer of 2-5 inclusive (especially 2 or 3 and sodium, potassium, ammonium and acid addition salts, such as lactate, phosphate, citrate and acetate salts, thereof.
  • Preferred compounds are those in which R, and R are alkyl groups having l4 carbon atoms, for instance methyl or ethyl.
  • These compounds 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 having the formula:
  • alkylene diamines are. for example, N-dodecyl-N', N-diethylethylenediamine. N-cetyl-N, N'-diethylethylenediamine, N-dodecyl-N', N-diethyltrimethylenediamine, and ,B-(dodecylamino)ethylmorpholine.
  • Preferred primary fatty amines are, for example, decylamine and dodecylamine. 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 coumpounds of formula l differing only in the value of the substituent R, the various R substituents being the various alkyl radicals present in tallow or copra acids respectively.
  • 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) maleamic acid is thus isolated in an almost quantitative yield and in a purity of 98 2
  • N',N'-diethyl-N-dodecylethylenediamine is dissolved in 300 ml of ethyl acetate.
  • 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 sodium salt of the maleamic acid of a mixture of primary amines derived from copra fatty acids in an analogous way to Example I.
  • EXAMPLE lV Preparation of the sodium salt of N' -lalkyhcopra)LN-(dodecyll-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 l.
  • EXAMPLE Vl Preparation of the potassium salt of N'--[alkyl(tallow)]-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 acid thus formed is neutralized 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.
  • the desired product is obtained in the form of a viscous oil.
  • 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 compound of the invention with a cationic product in current use.
  • EXAMPLE XII the condensate of 1 mole of octylphenol and 5 t 1x mulcwf ethylene oxide 7g when applied to the hair, imparts a glistening effect dicihanummide r copra (any acids 4 g thereto, softens it and makes it easy to comb.
  • EXAMPLE XVI lactic acid. qvs. for pH 5 water as. for 100 cc.
  • v i is 'ired: The mixture is allowed to cool to 40C and acidified The followmg on prep by the addition of citric acid until a pH of4 is reached, whereafter it is made up to 100 cc with water.
  • the hair thus acquires soft 13 9 f ethylefle l0 s U I V dicthanolamide of copra fatty acids 3 g ness and a gloss and is easy to comb.
  • lactic acid q's, [or pH 3 water qis, for 100 cc EXAMPLE XV There 18 thus obtained a VlSCOUS shampoo which The following mixture IS prepared: m k the hair supple and easy to comb.
  • Illustrative other detergent or shampoo detergents that may be used in the detergent or shampoo compositions include sodium lauryl sulphate. sodium decyl benzene sulphonate, N-(sodium sulphoethyl) oleamide. sodium dioctyl sulphosuccinatet sodium lauryl sulphoacetater etc.
  • Illustrative hair dyes that may be used in the hair dye compositions include l,4 diethylolamino-3-nitro ben zene. l-(,8-ethylolaminol-Z-amino-4-nitrobenzene. lhydroxy-2-amino-5-nitrobenzene. and direct dyes such as those shown in US. Pat. Nos, 1983.65 l $040,064, 3.049393. 3100.73). etc.
  • compositions of this invention have preferably an acid pH.
  • a surface acti ⁇ e composition having an acid pH comprising an effective amount of a surface active compound having the formula:
  • R and R are lower alkyl or together with the nitrogen atom on which they are attached constitute morpholino;
  • n is an integer of 2 to 5 and an aqueous carrier.
  • composition of claim 1 in the form of a gelv 3.
  • composition of claim 1 in which R and R are alkyl having l4 carbon atoms.
  • composition of claim 1 in which R and R and the N atom form morpholino.
  • composition of claim 1 which also contains an effective amount of a detergent compound.
  • composition of claim 1 which also contains an effective amount of a shampoo detergent 8.
  • the process of softening and conditioning live human hair comprising applying to the hair an effective amount of the composition of claim I.

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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 Kalopissis et al.
[ SURFACE ACTIVE COMPOSITIONS CONTAINING ASPARAGINE DERIVATIVES [75] Inventors: Gregoire Kalopissis; Andre Viout,
both of Paris; Guy Vanlerberghe, MOntjay-la-Tour, all of France [73] Assignee: LOreal, Paris, France [22] Filed: Feb. 12, 1970 [21] Appl. No.: 12,477
Related US. Application Data [63] Continuation-impart of Ser. No. 424,846, Jan. 11,
I965, Pat. NO. 3,534,032.
[30] Foreign Application Priority Data Jan. I7, 1964 France 64.60742 Mar. 25, 1975 [5 6] References Cited UNITED STATES PATENTS 2,821,521 l/l958 Price .I 260/534 X FOREIGN PATENTS OR APPLICATIONS 1,146,332 5/1957 France 424/70 l,344,2l2 lO/l963 France 2610/2472 Primary ExaminerStanley .I. Friedman Assistant Examiner-Vera C. Clarke Attorney, Agent, or FirmBrisebois & Kruger [57] ABSTRACT Surface active compositions which contain a surfaceactive compound having the formula R-NH-CH-COOH 2 in which R and R are an alkyl or alkenyl group which has 10-18 carbon atoms, R and R are lower alkyl Or with the N atom a morpholino group and n is 25.
9 Claims, N0 Drawings SURFACE ACTIVE COMPOSITIONS CONTAINING ASPARAGINE DERIVATIVES This application is a continuation-in-part of application Ser. No. 424,846, filed Jan. 11, 1965, now US. Pat. No. 3,534,032.
This invention relates to cosmetic compositions which contain new asparagine derivatives having surface-active properties, and to hair treating compsitions containing them.
US. Pat. Nos. 3,303,213 and 3,331,781 describe and claim asparagine derivatives having very interesting surfaceactive properties, which are of particular use in hair shampoos. 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 used in the compositions of this invention are compounds having the formula:
where R and R are each an alkyl or alkenyl group which has -18 carbon atoms which can be the same or different; R, and R are each lower alkyl, which can be the same or different, or together with the nitrogen atom to which they are attached constitute a morpholino residue and n is an integer of 2-5 inclusive (especially 2 or 3 and sodium, potassium, ammonium and acid addition salts, such as lactate, phosphate, citrate and acetate salts, thereof. Preferred compounds are those in which R, and R are alkyl groups having l4 carbon atoms, for instance methyl or ethyl.
These compounds 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 detergent 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 solutions which may contain 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 having the formula:
1 NH (CH N\ R NH where R has the meaning given above. Preferred alkylene diamines are. for example, N-dodecyl-N', N-diethylethylenediamine. N-cetyl-N, N'-diethylethylenediamine, N-dodecyl-N', N-diethyltrimethylenediamine, and ,B-(dodecylamino)ethylmorpholine.
Preferred primary fatty amines are, for example, decylamine and dodecylamine. 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 coumpounds of formula l differing 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 1 Preparation of the sodium salt of N -[alkyl(tallow)]-N-(dodecyl)-N-(N,N- diethylaminoethyl)asparagine.
l Preparation of N'N-diethyl-N-dodecylethylenediamine There are mixed with stirring 2 moles of dodecylbromide and 10 moles of N,N-diethylethylenediamine (96,6 the temperature being maintained below 50C. 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) maleamic acid.
One mole of N',N'-diethyl-N-dodecylethylenediamine is dissolved in 300 ml of ethyl acetate.
To this solution is added with stirring, in an hour and a half, 1 mole of maleic anhydride in solution in 300 ml of ethyl acetate, the temperature being maintained between 35 and 40C. 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 80 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 m1 of ethyl alcohol, and the solution is neutralized with a calculated quantity 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 C. for 11 hours. After evaporation of the alcohol. the product obtained takes the form of an oil dispersible in water, which contains 4 7! of unreacted primary amine.
EXAMPLE ll Preparation of the sodium salt of N -lalkyl(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 sodium salt of the maleamic acid of a mixture of primary amines derived from copra fatty acids in an analogous way to Example I.
EXAMPLE lll Preparation of the sodium salt of N -[alltyl(tallow)l-N-(cetyl)-N-(N.' l'-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-cetyLN-tN.N'-diethylaminoethyl)malea mate.
EXAMPLE lV Preparation of the sodium salt of N' -lalkyhcopra)LN-(dodecyll-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 l.
EXAMPLE V Preparation of the sodium salt of N -lalkyhtallow)l-N-(dodecyl) N-(morpholinoethyl- )asparagine.
By a process analogous to that described in Example I. there is obtained from dodecyl bromide and aminoethylmorpholine. ,B-(dodecylamino)ethylmorpholine.
The condensation of this diamine with maleic anhydride gives the corresponding maleamic acid which. after neutralization with sodium hydroxide. is reacted with the mixture ofprimary amines derived from tallow fatty acids yielding the desired product in the form of an oil.
EXAMPLE Vl Preparation of the potassium salt of N'--[alkyl(tallow)]-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 acid thus formed is neutralized 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 Vll Preparation of the sodium salt of N -[alkyl(copra)l-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 ofa viscous oil.
Examples Vlll to XVI below illustrate the use of compounds of the invention.
EXAMPLE VIII The following mixture is prepared:
sodium salt of N'-'-[alkyl(tallow)I-N-(dodccylla translucent gel is obtained.
EXAMPLE X There is prepared an aqueous solution containing:
the condensate obtained from 1 mole of tridec}! alcohol and [5 moles of ethylene oxide 7 diethanolamide of copra fatty acids 3 sodium salt of N"'-ltllk .l(tallow ll- N-t dodec l J-N-( N'.N'-diethylaniinoethyl )asparagine o g lactic acid. qs. for pH 5 water. q.s. l'or lUl) 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 compound 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 I2 moles of ethylene oxide 8 g diethanolamide of copra fatty acids 4 g sodium salt of N -[alkyl(Copra]-N-(N'.N"
diethylaminopropylJasparagine 3 g sodium salt of N -lalkyluallow )I-N- (dodecyll-N lN.N-dicthylaminoethyl)asparagine 6 g lactic acid. q.s. for pH 5 water. q.s. for ltll) 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 the condensate of 1 mole of octylphenol and 5 t 1x mulcwf ethylene oxide 7g when applied to the hair, imparts a glistening effect dicihanummide r copra (any acids 4 g thereto, softens it and makes it easy to comb. cet \ltrimethylammonium bromide 3 g sodium salt of N -lalkylflullow)l-N-(cetyll-N- rN'.N'diethylaminoethyl)asparagine o g EXAMPLE XVI lactic acid. qvs. for pH 5 water as. for 100 cc.
I The following mixture is prepared: A thick solution obtained. This product constitutes a shampoo which renders the hair very soft and makes h d v v nitroparap enylene iamine l g It eds) to Comb 15 diethanolamine of copra fatty acids 4 g the condensate of 1 mole of lauryl alcohol and EXAMPLE XI" l0 moles of ethylene oxide 6 g sodium salt of N -[alkyl(copra)]-N-(cetyl) There are prepared: -N-(N.N'-dicthylaminoethyl)asparagine 3 g acetic acid. q.s. for pH 5.5 water q.s. for 100 cc .il a \(llUllUll containing: 7 sULlILIm bromate l5 g Mm so g There 18 thus obtained a viscous dyeing solution h 3" i l l h I which, when applied to the hair, besides dyeing it, im- L C(l'l LllSZlIC O moe O CCU, 11 CO 0 l I and 5 mm M ethylene Oxide 2 g parts to it a gloss and suppleness. sodium ml! of N*-[alk \l(tallo\\ )]-N-(dodccyl)-N- iN.N'-d|ethylaminoethylJasparagine 3 g phosphoric acid. qs. for pH (15 EXAMPLE XV Llltfl' l5 2 The following mixture is prepared: a) and b) are mixed at about 40C and make up to I00 cc with water. There is thus obtained a creamy fix- Y sodium salt of N [alkyl(copra)]-N-(N,N'-diethylatnei ot which 100cc diluted with 150 cc of hot water amino prowl) asparaginc h are used to neutralize a permanent Wave. sodium salt of N -[alkylflallow)]-N-(dodecyl)- -N-(morpholino ethyl)asparagine 3 g EXAMPLE XIV the condensate of 1 mole of lauric alcohol and 12 moles of ethylene oxide 7 g Th r is re ared b conventional rocedure a diclhflnolflmifle 0f P y Acids 3 B L t p y p lactic acid. q.s. for pH 3 CI'ClllTl C(llllllll'llllgi water, q.s. lor l(l() cc hum It Niymkmmnu WMCCQNN There is thus obtained shampoo of viscous consislNN'mllclh)lumlnucllqllllspilrngll'lc 5 g tency which makes the hair very soft and easy to comb. cctyl alcohol 3 g the condensate of l niolc olstearyl alcohol 40 and Ill moles ofethylcnc oxide 3 g EXAMPLE XVI" HllCl' 70 CC.
v i is 'ired: The mixture is allowed to cool to 40C and acidified The followmg on prep by the addition of citric acid until a pH of4 is reached, whereafter it is made up to 100 cc with water. Gem trimehyi ammonium bromide 3 g From 5 to 10 g of this cream are applied to hair sensisfldlum $1111 01 N=l y l y -N-(morpholino ethyl) asparagine 3 g used y ll decolorutloni Whlch massaged for Several the condensate of 1 mole oflauric alcohol minutes and then rinsed. The hair thus acquires soft 13 9 f ethylefle l0 s U I V dicthanolamide of copra fatty acids 3 g ness and a gloss and is easy to comb. lactic acid q's, [or pH 3 water qis, for 100 cc EXAMPLE XV There 18 thus obtained a VlSCOUS shampoo which The following mixture IS prepared: m k the hair supple and easy to comb.
The mixtures of primary amines used in Examples 1 d I f Ni H I u H N d d I) to VII have been used commercially. so rum sa t o a \'(t;\ ow o ecy N-i N' N'-diethxliiminoethyl)asparagine 5 g Other illustrative surface active asparagine com plClumlC ma 045 g pounds having the formula I include:
H gm at /GH CH 0O N 0H H e 1 2 2 2 UK .a 000E C H NH 3 fri s! nmco-N-(cH)- o CH m CODE 2) c 1: NE
pH (v.5 llll) cc lactic acid q.s. for water. q.s. for
There is thus obtained a thick dyeing solution which Illustrative other detergent or shampoo detergents that may be used in the detergent or shampoo compositions include sodium lauryl sulphate. sodium decyl benzene sulphonate, N-(sodium sulphoethyl) oleamide. sodium dioctyl sulphosuccinatet sodium lauryl sulphoacetater etc.
Illustrative hair dyes that may be used in the hair dye compositions include l,4 diethylolamino-3-nitro ben zene. l-(,8-ethylolaminol-Z-amino-4-nitrobenzene. lhydroxy-2-amino-5-nitrobenzene. and direct dyes such as those shown in US. Pat. Nos, 1983.65 l $040,064, 3.049393. 3100.73). etc
The compositions of this invention have preferably an acid pH.
What is claimed is:
l. A surface acti\e composition having an acid pH comprising an effective amount of a surface active compound having the formula:
I /1 H-CON-(CH)-N i2 2n R-NH- H-COOH R $12 24 /CH9 co N (c11 rt 0 11 an a COOH t- 9 fiz a tc n H2-CO-N-(CH2)2-N 4) c 3 -NH-CH-COOH 35 or its sodium, potassium. or ammonium salt, wherein R and R are selected from the group consisting of alkyl having 10-18 carbon atoms and 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 morpholino;
and n is an integer of 2 to 5 and an aqueous carrier.
2. The composition of claim 1 in the form of a gelv 3. The composition of claim 1, in which n is 2 or 3.
4. The composition of claim 1, in which R and R are alkyl having l4 carbon atoms.
5. The composition of claim 1, in which R and R and the N atom form morpholino.
6. The composition of claim 1, which also contains an effective amount of a detergent compound.
7. The composition of claim 1, which also contains an effective amount of a shampoo detergent 8. The process of softening and conditioning live human hair comprising applying to the hair an effective amount of the composition of claim I.
9. The process of shampooing and softening live human hair comprising applying to the hair an effective amount of the composition of claim 7.

Claims (9)

1. A SURFACE ACTIVE COMPOSITION HAVING AN ACID PH COMPRISING AN EFFECTIVE AMOUNT OF A SURFACE ACTIVE COMPOUND HAVING THE FORMULA:
2. The composition of claim 1 in the form of a gel.
3. The composition of claim 1, in which n is 2 or 3.
4. The composition of claim 1, in which R1 and R2 are alkyl having 1-4 carbon atoms.
5. The composition of claim 1, in which R1 and R2 and the N atom form morpholino.
6. The composition of claim 1, which also contains an effective amount of a detergent compound.
7. The composition of claim 1, which also contains an effective amount of a shampoo detergent.
8. The process of softening and conditioning live human hair comprising applying to the hair an effective amount of the composition of claim 1.
9. The process of shampooing and softening live human hair comprising applying to the hair an effective amount of the composition of claim 7.
US012477A 1964-01-17 1970-02-12 Surface active compositions containing asparagine derivatives Expired - Lifetime US3873688A (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
NL123441D NL123441C (en) 1964-01-17
FR960742A FR1397231A (en) 1964-01-17 1964-01-17 New surfactants and their applications
US424846A US3534032A (en) 1964-01-17 1965-01-11 N - tertiaryaminoalkyl - n - aliphaticalpha aliphatic aminosuccinamic acid amides and corresponding maleamic acid intermediates therefor
CH47465A CH437644A (en) 1964-01-17 1965-01-13 Surface activity composition
CH121667A CH433374A (en) 1964-01-17 1965-01-13 Process for the preparation of new surfactants
BE658288D BE658288A (en) 1964-01-17 1965-01-14
NL6500541A NL6500541A (en) 1964-01-17 1965-01-15
GB1993/65A GB1058331A (en) 1964-01-17 1965-01-15 Amino acid surface-active compounds and their use in hair treatment compositions
GB40464/66A GB1058332A (en) 1964-01-17 1965-01-15 Improvements in or relating to the preparation of maleamic acid derivatives
DE19651518075 DE1518075A1 (en) 1964-01-17 1965-01-15 Process for the preparation of new asparagine derivatives and surfactants containing these derivatives
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

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
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

Publications (1)

Publication Number Publication Date
US3873688A true US3873688A (en) 1975-03-25

Family

ID=27445701

Family Applications (3)

Application Number Title Priority Date Filing Date
US424846A Expired - Lifetime US3534032A (en) 1964-01-17 1965-01-11 N - tertiaryaminoalkyl - n - aliphaticalpha aliphatic aminosuccinamic acid amides and corresponding maleamic acid intermediates therefor
US012477A Expired - Lifetime US3873688A (en) 1964-01-17 1970-02-12 Surface active compositions containing asparagine derivatives
US286698A Expired - Lifetime US3891385A (en) 1964-01-17 1972-09-06 Hair softening dye compositions containing surface-active asparagine derivatives

Family Applications Before (1)

Application Number Title Priority Date Filing Date
US424846A Expired - Lifetime US3534032A (en) 1964-01-17 1965-01-11 N - tertiaryaminoalkyl - n - aliphaticalpha aliphatic aminosuccinamic acid amides and corresponding maleamic acid intermediates therefor

Family Applications After (1)

Application Number Title Priority Date Filing Date
US286698A Expired - Lifetime US3891385A (en) 1964-01-17 1972-09-06 Hair softening dye compositions containing surface-active asparagine derivatives

Country Status (7)

Country Link
US (3) US3534032A (en)
BE (1) BE658288A (en)
CH (2) CH437644A (en)
DE (1) DE1518075A1 (en)
FR (1) FR1397231A (en)
GB (2) GB1058332A (en)
NL (2) NL6500541A (en)

Cited By (7)

* 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
US4089954A (en) * 1974-10-28 1978-05-16 Morelle Jean V Metal salts of fatty acid derivatives of amino acids
US4374056A (en) * 1980-11-27 1983-02-15 Kao Soap Co., Ltd. Lowly irritating detergent
US4584121A (en) * 1983-12-30 1986-04-22 Hoechst Akteingesellschaft Amphoteric compounds, mixtures containing these compounds for disinfectant cleaning, and processes for the preparation of these compounds and mixtures
US4652585A (en) * 1984-03-24 1987-03-24 Henkel Kommanditgesellschaft Auf Aktien N-substituted diaminopropane/glutamic acid reaction products
US5900213A (en) * 1993-04-28 1999-05-04 Alcon Laboratories, Inc. Use of diamines to disinfect and clean contact lenses and preserve ophthalmic compositions
US20100221503A1 (en) * 2008-06-24 2010-09-02 Dynaloy Llc Stripper solutions effective for back-end-of-line operations

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NL123441C (en) * 1964-01-17
US4020155A (en) * 1965-09-06 1977-04-26 Societe Anonyme Dite: L'oreal Surface active agents
US4402700A (en) * 1976-02-09 1983-09-06 Clairol Incorporated Composition for coloring hair containing an oxidizing agent and certain quaternary amines
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
US4076744A (en) * 1977-05-23 1978-02-28 Kewanne Industries, Inc. Amphoteric surfactants
DE2921366A1 (en) * 1978-05-26 1979-12-06 Albright & Wilson CONCENTRATED Aqueous SURFACE PREPARATION
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
US4755623A (en) * 1983-09-06 1988-07-05 American Cyanamid Company Polyfunctional amine crosslinker, process for making same, and compositions containing same
US4837012A (en) * 1987-06-19 1989-06-06 S. C. Johnson & Son, Inc. Hair reviver composition containing film-forming amino acids
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

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US2821521A (en) * 1954-08-25 1958-01-28 American Cyanamid Co Polymers of n-(dialkylaminopropyl) maleamic acid

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FR1146332A (en) * 1956-03-29 1957-11-08 Hair cleaning products and salts of bitertiary diamines used in the composition of these products
NL122204C (en) * 1959-08-08
US3331781A (en) * 1962-02-15 1967-07-18 Oreal Amphoteric surface-active agents and method of preparing them
NL123199C (en) * 1962-02-15
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US2821521A (en) * 1954-08-25 1958-01-28 American Cyanamid Co Polymers of n-(dialkylaminopropyl) maleamic acid

Cited By (8)

* 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
US4089954A (en) * 1974-10-28 1978-05-16 Morelle Jean V Metal salts of fatty acid derivatives of amino acids
US4374056A (en) * 1980-11-27 1983-02-15 Kao Soap Co., Ltd. Lowly irritating detergent
US4584121A (en) * 1983-12-30 1986-04-22 Hoechst Akteingesellschaft Amphoteric compounds, mixtures containing these compounds for disinfectant cleaning, and processes for the preparation of these compounds and mixtures
US4652585A (en) * 1984-03-24 1987-03-24 Henkel Kommanditgesellschaft Auf Aktien N-substituted diaminopropane/glutamic acid reaction products
US5900213A (en) * 1993-04-28 1999-05-04 Alcon Laboratories, Inc. Use of diamines to disinfect and clean contact lenses and preserve ophthalmic compositions
US20100221503A1 (en) * 2008-06-24 2010-09-02 Dynaloy Llc Stripper solutions effective for back-end-of-line operations
US8440389B2 (en) 2008-06-24 2013-05-14 Dynaloy, Llc Stripper solutions effective for back-end-of-line operations

Also Published As

Publication number Publication date
CH433374A (en) 1967-04-15
GB1058332A (en) 1967-02-08
DE1518075A1 (en) 1969-10-09
CH437644A (en) 1967-06-15
FR1397231A (en) 1965-04-30
US3534032A (en) 1970-10-13
BE658288A (en) 1965-07-14
GB1058331A (en) 1967-02-08
NL6500541A (en) 1965-07-19
NL123441C (en)
US3891385A (en) 1975-06-24

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