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Publication numberUS3793210 A
Publication typeGrant
Publication dateFeb 19, 1974
Filing dateSep 3, 1971
Priority dateJun 20, 1969
Publication numberUS 3793210 A, US 3793210A, US-A-3793210, US3793210 A, US3793210A
InventorsCorey G
Original AssigneeColgate Palmolive Co
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Keto acid containing compositions
US 3793210 A
Abstract
Improved surfactant and shampoo compositions which have improved solubility and foaming characteristics, which compositions comprise a keto acid in combination with surfactants, brighteners, conditioners, and the like.
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Description  (OCR text may contain errors)

United States Patent 1 Corey 1 Feb. 19, 1974 KETO ACID CONTAINING COMPOSITIONS [75] Inventor: Garland George Corey, Milltown,

[73] Assignee: Colgate-Palmolive C0., New York,

[22] Filed: Sept. 3, 1971 21 Appl. No.: 177,855

Related US. Application Data [63] Continuation of Set. No. 835,256, June 20, 1969,

abandoned.

[52] US. Cl 252/89, 252/132, 252/D1G. 13, 424/70 [51] Int. Cl Clld 3/20 [58] Field of Search. 252/89, DlG. 13, 132; 424/70; 260/526 R Primary Examiner-William E. Schulz [5 7 ABSTRACT Improved surfactant and shampoo compositions which have improved solubility and foaming characteristics, which compositions comprise a keto acid in combination with surfactants, brighteners, conditioners, and the like.

8 Claims, N0 Drawings KETO ACID CONTAINING COMPOSITIONS This is a continuation of application Ser. No. 835,256 filed June 20, 1969 now abandoned.

The instant invention is directed to novel surfactant and shampoo compositions. In particular, the instant invention is directed to surfactant and shampoo compositions which contain keto acid.

There are numerous types of shampoos and surfactant compositions on the market at present. Many of these compositions are based on soaps although there are numerous compositions which contain synthetic detergent preparations. Such detergent preparations contain primarily organic sulfates and sulfonates. These detergent compositions are favored by many consumers because they do an extremely thorough cleaning job and further do not leave dulling lime soaps on the hair when hard water is employed.

Under the conditions of use the synthetic detergents are better cleaners in that they effectively remove excess oils from the hair. Furthermore, the hair is more easily washed with said detergents than with soap because the use of soap requires that it be removed as thoroughly as possible from the hair by asubsequent prolonged rinsing treatment with water, which may leave behind an undesirable degree of alkalinity on the scalp.

In connection with shampoo compositions it is noted that most users of shampoos have definite requirements with respect to the performance characteristics of the products they use. A shampoo which merely cleans the hair is not necessarily a satisfactory product; it is often said that a shampoo which cleans too well is unsatisfactory. In addition to cleaning adequately, the product must lather well during the shampooing operations and must condition the hair, i.e., leave the hair in a soft, smooth, lustrous and easily manageable state. The sham poo must be mild and have sufficient resistance to hard water since hard water may cause a reduction in lather and cleaning efficiency and may cause an undesirable film formation on the hair. The use of softened water or special rinses are not satisfactory solutions to hard water problems for a commercially acceptable shampoo.

The chief problem in formulating a shampoo which has the combination of the requisite properties is that a particular ingredient which will impart to the shampoo one or perhaps several of the requisite properties in an outstanding manner will adversely affect one or more of the remaining properties. For example, soapbased shampoos, in soft water, have excellent cleaning, lathering and hair conditioning properties; however, any hardness in water adversely affects the lathering characteristics and leaves the well known undesirable hard water soap curd. Sequestering and curd dispersing additives have improved soap shampoos to some extent but the majority of successful shampoos are based on those non-soap synthetic detergents which lather and clean well in hard or soft water. Such non-soap detergents, however, have the shortcoming of cleaning so well that the natural oil of the hair, which naturally conditions the hair, is removed leaving it harsh and unmanageable.

If the shampoo preparation is designed to preserve much of the natural oil in the hair, the criticism can be voiced that it does an incomplete cleaning job. Some shampoos attempt to solve this problem by using a highly effective detergent with a hair conditioning agent which serves as a replacement for the oil removed from the hair. Examples of such hair condioning agents are polyglycols, fatty acid esters of glycols, natural or synthetic waxes, and lanolin derivatives. Use of formulations containing excessive amounts of hair conditioning agents of the oily type may cause the hair to have an unpleasant oily appearance and feel. Formulations containing certain hair conditioning agents suffer from the additional difficulty that the oily material inhibits sudsing of the shampoo. Most people have come to expect copious lather from their shampoo and are dissatisfied if it is not formed.

It is an object of this invention to provide a homogeneous shampoo which produces a copious lather, effectively cleans the hair, and leaves the hair, after drying, in a soft, lustrous, easily manageable condition.

It is another object of this invention to provide a shampoo which has the above characteristics in hard as well as soft water and which does not form an undesirable hard water precipitate.

It has been found that these and other objects of the instant invention can be obtained by providing a shampoo composition which includes a keto acid in combination with other conventional shampoo ingredients. For the purposes of the present invention, it is intended that the term keto acid be generic to encompass not only ketone acids but aldehyde acids as well, i.e., acids containing an oxo-carbonylic group. The keto acids employed is connection with the instant invention have the general formula:

0 i R (CHmCOOI-I wherein R represents hydrogen or an alkyl such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, eicosyl, and the like, and n represents an integer of from O to 3. These keto acids are all well known in the art and may be prepared in a known manner. Suitable keto acids include, but are not limited to, the following:

ll CH CI-I CH CH CH CCOOH C CI-ICH COOH if CH CH CHCH COOH CH ,cmcmcn iincn cn coou cn,cn,cn cmcmiincncn cn coon o I-ICH CH CH COOH 0 l cmdncmcincmcoon CHQCHZCHCHZCHZCHZCOOH ll cH,cH,cn,ci-|cn,cr|,cn,cooii In addition to theessential keto acid one may employ in connection with the instant shampoo composition any of the usual ampholytic surface active agents or detergents. Among those which provide best results are the fatty imidazolines, such as l-coco-5-hydroxyethyl- S-carboxymethyl imidazoline known as Miranol CM, and other similar products made by reacting monocarboxylic fatty acids having chain lengths of to 24 carbon atoms with diethylene triamine and with monohalo monocarboxylic fatty acids having from 2 to 6 carbon atoms, the fatty beta-alanines such as dodecyl beta-alanine sold under the name dodecyl Deriphat, the inner salt of Z-trimethylamino lauric acid sold under the name Product BDO, betaines such as N- dodecyl-N,N-dimethylaminoacetic acid sold under the name Quatronyx, etc. Mixtures of any two or more of the foregoing may be employed.

In addition to' ampholytic detergents one may also employ nonionic surface active agents or mixtures thereof. Among the useful nonionic surface active agents are the the ethylene oxide ethers of alkyl phenols such as nonylphenol polyoxyethylene ether, the ethylene oxide ethers of fatty alcohols. such as tridecyl alcohol polyoxyethylene ether, the ethylene oxide ethers of alkyl mercaptans such as dodecyl mercaptan polyoxyethylene thioether, the ethylene oxide esters of the fatty acids such as lauric ester of polyethylene glycol and lauric ester of methoxy polyethylene glycol, the ethylene oxide ethers of fatty acid amides, the condensation products of ethylene oxide with partial fatty acid esters of sorbitol. such as the lauric ester of sorbitan polyethylene glycol ether, and other similar materials.

In addition, one may also employ a wide variety of cationic surface active agents including distearyl dimethyl ammonium chloride, stearyl dimethylbenzyl ammonium chloride, coco dimethylbenzyl ammonium chloride, dicocodimethyl ammonium chloride, cetylpyridinium chloride, cetyltrimethyl ammonium bromide, the stearyl amine salts that are soluble in water such as stearyl amine acetate and stearyl amine hydrochloride, stearyl dimethylamine hydrochloride, distearyl amine hydrochloride, octyl phenoxyethoxyethyl dimethylbenzyl ammonium chloride, decyl pyridinium bromide, the pyridinium chloride derivative of the acetylaminoethyl esters of lauric acid, lauryl trimethyl ammonium chloride, decylamine acetate, lauryl dimethylbenzyl ammonium chloride, and the like. Mixtures of two or more cationic surface agents may be employed if desired.

Still further, one may employ anionic surface active agents such as and including but not limited to the alkyl sulfates such as sodium lauryl sulfate, the fatty taurides such as cocomethyl tauride and tallow methyl tauride, the sulfated monoglycerides, the sulfonated monoglycerides, the alkyl aryl sulfonates, lauryl hydroxy ether lauryl propionate, coconut acid ester of sodium isethionate, dioctyl ester of sodium sulfosuccinic acid, N- octa decyl tetrasodium l,2-dicarboxyl ethyl sulfosuccinate),,.ammonium salt of sulfate ester of an alkyl phenoxy polyoxyethylene ethanol, sodium salt of lauryl polyoxyethylene sulfate, sodium salt of tridecyLether polyoxyethylene sulfate, fatty acid amido polyoxyethylene sulfate, and the like, as well as mixtures thereof.

In addition to the detergentand keto acid, the instant shampoo compositions also include a solvent such as water, alcohol, isopropanol, glycerine, and the like. Furthermore, any of the conventional additives such as preservatives, dyes, pearling agents, perfumes, thickeners, opacifiers andthe like may be included in accordance with conventional compounding practice. Fur thermore, one may also include UV absorbers, thickeners, formaldehyde and conditioners as are conventionally employed in shampoo compositions.

One may employ in connection with the compositions of the instant invention from about 5 to about 40 percent detergent ingredient. In addition, with regard to the keto acids, from aboutO.5 percent to about 10 percent by weight is employedin connection with the compositions. i

As previously noted, we have unexpectedly found that when one employs the above-delineated keto acids in a surfactant composition, one obtains an increase in the foaming properties thereof and furthermore, an unexpected improvement in the conditioning aspects of the shampoo systems. This phenomenon is particularly noted when the keto acids are employed in connection with acidic systems, i.e., surfactant compositions having a pH of from about 3 to about 7, whereupon, in addition to the above aspects, the keto acids also serve to increase the solubility of the detergent systems. i

The instant invention will now be further'explained by the following examples. It is noted that the instant invention is not deemed as being limited thereto.

EXAMPLE 1 A surfactant composition was prepared according to the following formulation:

Triethanolamine lauryl sulfate Alcohol 5.5% Lauryl myristic diethanolamide 5% Phosphoric acid 10% Water The pH of the above system was adjusted with sodium hydroxide to a pH of 5.5. 3 grams of the product was mixed with 50 grams of tap water in a 500 milliliter graduated cylinder. The cylinder was stoppered and inverted times and the amount of foam was read in cc's. As a result of this experiment, it was found that the sample had 250 ccs of foam.

EXAMPLE 2 EXAMPLE 3 The procedure of Example 1 was repeated with the composition of Example 1 with the exception that distilled water was employed instead of tap water. As a result of the experiment the sample was found to produce 225 ccs of foam.

EXAMPLE 4 The procedure of Example 2 was repeated with the exception that distilled water was employed instead of tap water. As a result of the experiment the sample was found to produce 275 ccs of foam.

EXAMPLE 5 A shampoo formulation was compounded according to the following formula:

Triethanolamine lauryl sulfate l9% Alcohol 5.5% UV absorber 0.4% Methyl cellulose 0.9% Lauryl myristic diethanolamide 5% Water to l00% The procedure of Example 1 was repeated and as a result the composition was found to produce 325 cos of foam.

EXAMPLE 6 The composition of Example 5 was prepared with the exception that 5 percent acetoacetic ethylate was added thereto. As a result of the procedure of Example 5 the composition was found to produce 350 ccs of foam.

EXAMPLE 7 The composition of Example 2 was prepared, with the exception that in lieu of 7.3 percent levulinic acid, 9% glyoxylic acid was employed. The procedure of Example 2 was repeated and the sample was found to produce 425 ccs of foam.

EXAMPLE 8 The procedure of Example 4 was repeated, with the exception that 5 percent glyoxylic acid was employed instead of 7.3 percent levulinic acid. As a result of the experiment, the sample was found to produce 240 ccs of foam.

EXAMPLE 9 The procedure of Example 6 was repeated, with the exception that 2 percent pyruvic acid was employed in lieu of 5 percent acetoethylate. As a result of the experiment, the composition was found to produce 340 ccs of foam.

As will readily be noted from the above Examples, when one adds a keto acid to a shampoo formulation, one obtains an unexpected increase in the foaming action thereof. It is also to be noted that by employing a keto acid in the shampoo compositions, one also obtains unexpected conditioning, softening and cleaning characteristics from the resulting shampoo composition.

What is claimed is:

l. A detergent composition consisting essentially of from about 50 to about 94.5 percent water, from about 5 to about 40 percent detergent selected from the group consisting of ampholytic, nonionic, cationic and anionic surfactants and mixtures thereof and from about 0.5 to 10 percent of a keto acid of the formula wherein R is hydrogen or an alkyl group having from 1 to about 20 carbon atoms and n is O to 3.

2. The composition of claim 1 wherein said keto acid is chosen from the group consisting of levulinic acid, glyoxylic acid and pyruvic acid and mixtures thereof.

3. The composition of claim 1 wherein said composition has a pH of from about 3 to about 7.

4. The composition of claim 1 wherein the surfactant is diethanolamine lauryl sulfate.

5. A detergent composition consisting essentially of from about 50 to 94.5 percent water, from about 5 to about 40 percent detergent selected from the group consisting of ampholytic, nonionic, cationic and anionic surfactants and mixtures thereof and from about 0.5 to 10 perce'nt of a keto acid of the formula wherein R is hydrogen or a methyl group and n is 0 to 3.

6. The composition of claim 5, wherein said keto acid is glyoxylic acid.

7. The composition of claim 5, wherein said keto acid is pyruvic acid.

8. The composition of claim 5 wherein the keto acid is levulinic acid.

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US2674580 *Jul 20, 1950Apr 6, 1954Colgate Palmolive CoLiquid shampoo
US3218234 *May 13, 1963Nov 16, 1965WilmsmannTreatment of proteinaceous materials with pyruvic acid or glyoxylic acid to remove peroxides
US3267136 *May 9, 1963Aug 16, 1966People Of Puerto RicoProcess for producing levulinic acid
US3451937 *May 16, 1968Jun 24, 1969Procter & GamblePhosphonate compounds
US3524877 *Jun 17, 1966Aug 18, 1970Akademie Der Wissenchaften ZuMethod of producing keto acids
US3590122 *May 12, 1967Jun 29, 1971Colgate Palmolive CoShampoo composition
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US4380549 *Mar 23, 1981Apr 19, 1983Scott Eugene J VanTopical treatment of dry skin
US8877184Jul 19, 2010Nov 4, 2014Colgate-Palmolive CompanyCleaning composition with decyl and coco glucosides
WO2008046808A1 *Oct 15, 2007Apr 24, 2008Basf AgUse of keto acids in cleaners for odor control
WO2012011892A1 *Jul 19, 2010Jan 26, 2012Colgate-Palmolive CompanyCleansing composition with decyl and coco glucosides
Classifications
U.S. Classification510/426, 510/127, 424/70.27, 424/70.22, 424/70.21, 424/70.31
International ClassificationA61K8/365, A61K8/30, A61Q5/02, C11D3/20
Cooperative ClassificationA61Q5/02, C11D3/2075, A61K8/365
European ClassificationA61Q5/02, C11D3/20E, A61K8/365