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Publication numberUS2930761 A
Publication typeGrant
Publication dateMar 29, 1960
Filing dateMar 25, 1957
Priority dateMar 29, 1956
Publication numberUS 2930761 A, US 2930761A, US-A-2930761, US2930761 A, US2930761A
InventorsEdouard J-F Charret
Original AssigneeOreal
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Hair cleansing composition
US 2930761 A
Abstract  available in
Previous page
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Claims  available in
Description  (OCR text may contain errors)

United States Patent HAIR CLEANSING COMPOSITION Edouard L-F. Charret, Caluii'e, France, assignor to Societe Monsavon-LOreal (Soeiete Anonyme), Paris, France, a company of France N0 Drawing. Application March 25, 1957 Serial 'No. 647,962

Claims priority, application France March 29, 1956 2 Claims. (Cl. 252-152) This invention relates to materials and methods for cleansing the hair and particularly to compositions containing ditertiary diamines and their use.

Anionic surface-active products such as alkyl-aryl-sulphonates and alkyl-sulphates, as usually employed for cleansing the hair have the advantage of being good detergents and having good foaming power. On the other hand, they have the disadvantage that they remove from the hair natural fatty substances to which it owes its flexibility and its lustre, and they thus render it dry and brittle. They are generally employed in an alkaline medium and cannot be used in a neutral or acid medium. These products do not act as softeners, this term being used in the sense in which it is usually employed in textile fibre treatment, that is to say, they do not facilitate the sliding of the hairs one upon the other and do not facilitate the application of dyes.

It is also known that some non-ionic surface-active products can be employed for cleansing the hair. Such products are also good detergents and have good foaming power. They are free from some of the disadvantages of anionic products, but they also have no softening effect on the surface of the hair.

Some cationic surface-active products, such as quaternary ammonium salts and long-chain aliphatic amine salts, have also been proposed as products for cleansing the hair. They are generally rather poor detergents and they have the disadvantage of being noxious to the scalp. On the other hand, they have good softening properties, which also promote dyeing.

It has now been discovered, however, that certain ditertiary aliphatic diamines substantially afford all the advantages required of a product for cleansing hair.

According to a first feature of the present invention there are provided compositions for use in cleansing the hair which comprise aqueous dispersions or solutions of at least one ditertiary aliphatic diamine of the general Formula I:

R1 R! (I) wherein R represents a saturated or unsaturated straight or branched aliphatic group containing from 12 to 22 carbon atoms, two of the groups R R and R represent groups of the formula -(CH ),,OH and the other represents a group of the formula where x is 2 or 3 and n is nought or 1, or salt of such diamine, the composition having a pH of 3.5 to 6.

According to a further feature of the invention a process of cleansing hair comprises applying thereto an aqueous composition as defined above.

.In practice, compounds of Formula I are preferably used inthe form of aqueous solutions or aqueous sols of their salts, as will hereinafter be explained in greater 2,930,761 Patented Mar. 29, 1960 tached to the nitrogen atom.

They can be prepared from fatty amines or mixtures of fatty amines by the following process:

(1) A molecule of alkylamine RNH is condensed with a molecule of acrylic nitrile to obtain the corresponding alkyl-amino-propionitrile in accordance with the reaction:

(2) The alkyl-amino'propionitrile is converted into alkyl-amino-propylamine by catalytic hydrogenation in accordance with the reaction:

(3) Three or four molecules of ethylene oxide or pro pylene oxide are attached to one molecule of the alkylamino-propylamine by the conventional method of fixing ethylene oxide or propylene oxide on amines in accordance with the reactions (shown for ethylene oxide):

It is necesnary to ensure that the three hydrogen atoms fixed on the two nitrogen atoms of the alkylaminopropylamine are substituted by the group -(CH ),,OH or [(CH ),,O],,(CH OH, so as to obtain solely tertiary amine groups, and thus to eliminate completely the noxious action of secondary or primary amine groups on the epidermis. It is for this reason that it is advantageous to fix at least three molecules of ethylene oxide or propylene oxide on one molecule of alkylaminopropylamine without, however, exceeding four molecules. If four molecules are exceeded, the foaming power of the salts of the hydroxyethylated or hydroxypropylated alkylaminopropylamine is decreased.

Excellent products are obtained which have very high foaming power and are completely harmless to the skin by fixing, for example, an average of 3.5 molecules of ethylene oxide or propylene oxide on 1 molecule of alkylaminopropylamine.

The alkylaminopropylamines thus hydroxyethylated or hydroxypropylated are not soluble in water, but they can be dispersed in water. On the other hand, the majority of their salts are soluble in water.

Salts. of the compounds-of Formula I can be formed with various mineral or organic acids. Mineral acids such as' hydrochloric acid or phosphoric acid may be employed. However, it is preferred to employ salts formed from fatty acids of low molecular weight-such as formic CHa-CHzOH ample. Any acid giving water-soluble salts with the compounds of Formula I may be employed. However, it will be advantageous to employ acids which are most compatible with the skin, notably hydroxyacids, such as lactic acid, whichin addition gives an unctuous foam.

For preparing solutions. ready for use, one or more compounds of Formula I heated at 7080' C., are neutralised by adding with good agitation, an aqueous solution heated at the same temperature of the acid employed. The pH of the solution obtained'may range from 3.5 to 6, depending upon the acid employed. Solutions of salts having a more acid pH lose some of their foaming power, and those with more alkaline pH lead to hydrolysis of the salts and deposition of cationic base.

It is advantageous to adjust the pH to between 3.5 and 5 by slowly adding the solution of the acid and controlling I j the pH thereof. After neutralisation, the solution is allowed to cool before being perfumed, if desired, and before being packed.

It is an advantage of the salts of compounds of l 4 to repel it. The hairbecomes anti-static and less readily takes up' dust in suspension in the air. The following examples will serve to illustrate the invention:

Formula I that in many cases, at normal temperature,

they form more or less viscous liquids or gels which liquefiy on heating, depending upon their concentration. These liquids and gels constitute suitable compositions according to the invention. Thus, an aqueous solution containing 50% by weight of the dilactate of a compound of Formula I in which R has a chain length of 18 carbon atoms (oleyl or stearyl) is fluid at 60 C. On

a cooling to below 50 C., it sets in the form of a plastic,

homogeneous gel. Such a gel can be packed in tubes and used without any addition of gelling or thickening agent. On the other hand, an aqueous solution containing by weight of the said dilactate remains fluid and limpid at room temperature and can be marketed in liquid form.

Shampoos prepared with solutions of salts of compounds of Formula I give an abundantand consistent lather. The detergent action is such that all dirt on the hair is eliminated at the first wash and rinsing is simple. Owing to the fact that they are both cationic and nonionic, the salts of compounds of Formula I are insensitive to acid pH and to the alkaline-earth metal salts contained in the washing water. No deposition emanating from the product itself or from an action of the product on salts contained in the water takes place on the hair.

Moreover, it appears that, probably owing to their low cationic activity, the salts of compounds of Formula I are not completely eliminated from the surface of the hair on rinsing but leave a layer of molecular proportions resistant to rinsing. The following are the principal EXAMPLE I Dilactate' of N-hydroxyethyl-N'-di-(hydroxyethyl)- oleylamz'nwpropylamine in fluid aqueous solution Ethylene oxide is reacted with l gram"molec ule of ole'ylamino-propylamine, i.e. 324 g., until the weight is increased by 132 g. I i

To the 456. .g. of, ,N-hydroXyethyl-NGdL(hydroxyethyl)-oleylamino-propylamine thus obtained, heated at 75 C., there is slowly addedwith agitation a solution of 225 g. ors0% lactic acid in 1430 g. of water, heated at 60 C. The pHis adjusted to 6.0.

On cooling, a limpid 30% solution of N-hydroxyethyl-N-di-(hydroxyethyl) -,oleylamino propylamine lactate is obtained. This solution can be directly used as a liquid shampoo.

7 EXAMPLE H Dilactate of N-hydroxyethyl- N'-hydr0xyethyl-N'-(h droxyeihoxyethyl) alkyl-(tallow) -amino p ropylamine,

' in the form of a paste Four molecules of ethylene oxide are reacted with one molecule, i.e. 320 g. of alkylamino-propylamine the alkyl chain correspondingto the mixture ofthe chains of the fatty acids derived from tallow), until the weight is increased by 176 g. g V

To the 496 g. of product thus obtained,heated at 80 C., is slowly added with agitation a solution of 225 g. of 80%lactic acid in 631 g. of Water, the solution'having been heated'to 80 C. y i

The solution is allowed. to cool and a consistent and translucent gel is obtained, which can be directly employed as a concentrated shampoo.

EXAMPLE III A 30% clear aqueous solution of N-hydroxyethyl-N'- di-(hydroXyethyl)-oleylamino-propylamine dilactate was prepared as described in Example I.

An effective shampoo with pH 4.2 is obtained with the following ingredients:

1 Parts 30% solution of the aforesaid dilactate 92 I Hydrochloric acid (22 B.) 2

advantages of the products prepared in accordance with the invention:

(i) Afterwashing and rinsing, the hair has an extremely glossy appearance and a remarkable lustre.

(ii) It is particularly soft to the touch and can be combed and disentangled without effort as if it were lubricated.

(iii) Setting and permanent waving are easier to carry out and hold better, the hair appearing to have more spring than after washing with the shampoos usually employed.

(iv) Like all detergents having more or less pronounced cationic properties, the products defined in the present invention promote the development of dyes on the hair.

(v) The layer of molecular dimensions deposited on the surface of the hair reverses the static electric charge Water to make up parts,

EXAMPLE IV A solution effective for washing hair and having a pH of 4 is prepared from: I

- Parts N-hydroXyethyl-N'-di-(hydroxyethyl) oleyl'aminopropylamine (in the form of the base) 26 Hydrochloric acid (22-B.) 10.5 Water to make up 100 pants.

I claim: a

1. A composition for cleansing live human hair comprising an aqueous solution of the dilactate of N-lrydroxyethyl N di(hydroxyethyl) oleylamino propylamine of pH 3.5 to 6. 7

2. A composition for cleansing live human hair comprising an aqueous solution of the dilactate of N-hydroxyethwl-N' di(hydroxy ethoxyethyl) alkyl propylamine wherein the alkyl group is derived from thefatty acids of tallow, said solution having a pH of 3.5 to 6.

Schoeller et al. Sept.'10, 1940 a

Patent Citations
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US2214352 *Jun 17, 1936Sep 10, 1940Gen Aniline & Film CorpProcess for the production of condensation products containing onium groups
US2717909 *Sep 24, 1953Sep 13, 1955Monsanto ChemicalsHydroxyethyl-keryl-alkylene-ammonium compounds
US2794765 *Aug 8, 1955Jun 4, 1957Ciba LtdCosmetic preparations
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3090795 *Aug 11, 1960May 21, 1963Universal Oil Prod CoEsters of carboxylic acids and the condensation products of epihalohydrin and an aliphatic amine
US3090796 *Aug 11, 1960May 21, 1963Universal Oil Prod CoCarboxylic acid salts of the condensation product of epihalohydrin and an aliphatic amine
US3378581 *Jul 31, 1961Apr 16, 1968Nalco Chemical CoDiamine salts useful for inhibiting the corrosion in return steam condensate lines
US3398197 *Feb 23, 1965Aug 20, 1968Armour Ind Chem CoNu-secondary-alkyl tertiary amine compounds
US3418374 *Nov 9, 1964Dec 24, 1968Armour & CoFatty polyamines and their alkyl and alkoxy derivatives
US3725473 *Nov 28, 1969Apr 3, 1973Colgate Palmolive CoN-(2-hydroxyhydrocarbonyl) iminodicarboxylates
US3905932 *Mar 19, 1974Sep 16, 1975Toyo Soda Mfg Co LtdProcess for preparing polychloroprene latex
US3975295 *Aug 26, 1974Aug 17, 1976Ashland Oil, Inc.Liquid amine compositions
US4012398 *Sep 16, 1975Mar 15, 1977Van Dyk & Company, IncorporatedQuaternary halides of mink oil amides
US4083872 *Jan 30, 1976Apr 11, 1978Deutsche Gold- Und Silber-Scheideanstalt Vormals RoesslerN-2,3-Dihydroxypropyl-N-2-hydroxyalkyl-amine and its salts
US5098604 *Mar 28, 1989Mar 24, 1992Ceca, S.A.Cation-active compositions and their application to bituminous emulsions
US5145608 *Jan 7, 1991Sep 8, 1992Ecolab Inc.Ethoxylated amines as solution promoters
EP0051030B1 *Oct 23, 1981Apr 10, 1985Ceca S.A.Preparation of emulsions of hydrocarbon binders by using emulsifiers based on specific oxalkylated fatty diamines
EP0059383B1 *Feb 19, 1982Jun 18, 1986Dainippon Pharmaceutical Co., Ltd.Improver for the color fastness of dyed cotton textiles to chlorinated water and process for improving the color fastness of dyed cotton textiles to chlorinated water
U.S. Classification510/119, 516/DIG.700, 516/15, 510/499, 564/493, 564/506, 510/488, 564/475
International ClassificationA61K8/41, A61Q5/02
Cooperative ClassificationY10S516/07, A61K8/416, A61Q5/02
European ClassificationA61Q5/02, A61K8/41L