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Publication numberUS3703481 A
Publication typeGrant
Publication dateNov 21, 1972
Filing dateJan 25, 1971
Priority dateJan 25, 1971
Also published asCA938557A1
Publication numberUS 3703481 A, US 3703481A, US-A-3703481, US3703481 A, US3703481A
InventorsGraham Barker, Herman W Campbell
Original AssigneeWitco Chemical Corp
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Aqueous-based cosmetic detergent compositions
US 3703481 A
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Description  (OCR text may contain errors)

United States Patent Ofice 3,703,481 Patented Nov. 21, 1972 3,703,481 AQUEOUS-BASED COSMETIC DETERGENT COMPOSITIONS Graham Barker, Fair Lawn, N.J., and Herman W. Campbell, Chicago, Ill., assignors to Witco Chemical Corporation, New York, N.Y. No Drawing. Filed- Jan. 25, 1971, Ser. No. 109,614 Int. Cl. Clld 1/20 US. Cl. 252546 11 Claims ABSTRACT OF THE DISCLOSURE This invention relates to improved detergent and surfactant compositions. More particularly, this invention relates to improved aqueous-based cosmetic detergent compositions having improved characteristics with regard to emolliency, wetting, lathering, hair manageability, counter-irritancy and the like.

Surfactant compositions, including cosmetic surfactant compositions such as shampoos, shaving creams, skin cleansing compositions and the like, containing various derivatives of polycarboxylic acids are known to the art and are disclosed, for example, in US. Pats. No. 2,452,- 043, issued Oct. 26, 1948 to Lawrence H. Flett; No. 2,490,459, issued Dec. 6, 1949 to Werner Max Lilienfeld; -No. 2,562,154, issued July 24, 1951 to Emil A. Vitalis; and 2,878,190, issued Mar. 17, 1959 to Vladimir Dvorkovitz et al. Compounds therein disclosed include, among others, succinic acids, sulfosuccinic acids, sulfosuccinamic acids, esters, sulfosuccinic esters of fatty alkanolamides and salts thereof and various derivatives thereof, and are reported as useful in surfactant compositions, particularly shampoos. However, the aforesaid have numerous deficiencies preventing their use in a wide variety of aqueous-based surfactant compositions as opposed to the fatty alkanolamide monoester salt additives more particularly described herein.

In accordance with the present invention, there have been discovered improved aqueous based cosmetic detergent compositions comprising water, a member of the group of synthetic anionic, nonionic and cationic organic detergents and compatible mixtures of same, and from about 1 to 20%, preferably 3 to by weight, of a member of the group of ammonium, C -C alkanolamine and alkali metal salts of the monoester of a C -C saturated, unsubstituted, aliphatic dicarboxylic acid with fatty acid monoand dialkanol-amides wherein the alkanol portion contains up to 8 carbon atoms.

The compositions of the present invention contain, as an essential ingredient, from about 1 to 20%, by weight, of an aforesaid salt of a monoester of a C -C saturated, aliphtic dicarboxylic acid such as succinic, malonic, glutaric or adipic acid with a fatty acid alkanolamide.

The fatty acid alkanolamides are well known to the art and generally comprise those prepared from saturated and unsaturated aliphatic monocarboxylic acids containing from about 8 to 22 carbon atoms and preferably those containing from about 10 to 18 carbon atoms. Exemplary fatty acids are caprylic, capric, lauric, myristic, palmitic, stearic, arachidic, behenic, oleic, linoleic and eleostearic acids and the like, as well as mixed fatty acids such as tall oil fatty acids, hydrogenated tallow fatty acids, coconut oil fatty acids and vegetable fatty acids such as are derived from cottonseed and soybean oil, as well as rosin fatty acids. The alkanolamines which may be condensed with the aforesaid fatty acids comprise both monoand dialkanolamines containing up to 8 carbon atoms and are exemplified by monoethanolamine, diethanolamide, isopropanolamine, diisopropanolamine, butanolamine, dibutanolamine, diisobutanolamine and the like. These fatty acid alkanolamides may be prepared by various well known techniques such as by condensing equimolar quantities of fatty acid with alkanolamine, or by condensing a molar excess of alkanolamine with fatty acid or by reacting a fatty acid ester with alkanolamine, or by oxyalkylating, such as oxyethylating, the amide of the fatty acid. Particularly preferred fatty alkanolamides are fatty acid monoalkanolamides, particularly monoethanolamides.

The monoesters are prepared, for instance, by reacting appropriate substantially stoichiometric quantities of C -C aliphatic saturated dicarboxylic acids with the aforesaid fatty acid alkanolamides in order to prepare fatty acid alkanolamidedicarboxylic acid monoesters having one free COOH available for salt formation. The fatty acid alkanolamide is preferably esterified with succinic acid. The monoester salts may be the water-soluble ammonium, C -C alkanolamine such as ethanolamine, diethanolamine, triethanolamine, isopropanolamine, diisopropanolamine and the like, or alkali metal salts, of the aforesaid monoesters of the fatty acid alkanolamides with dicarboxylic acids. Preferably the monoester salt will be the sodium salt.

The aforesaid salts of fatty acid alkanolamide-dicarboxylic acid monoesters are employable in a wide variety of aqueous-based cosmetic detergent compositions. These cosmetic detergent compositions will generally contain, in addition to the aforesaid salt of a fatty acid alkanolamide-dicarboxylic acid monoester present in amounts varying between 1 and 20%, preferably 3 to 10%, by weight, a quantity of water in the range of about 10 to by weight, and the balance will be a member of the group of synthetic organic detergents of the anionic, nonionic or cationic type.

The particular synthetic organic detergent, surfactant, soap or mixture thereof chosen for employment in the compositions of the prevent invention will be dependent upon the particular cosmetic preparation sought to be prepared. The compositions of the present invention encompass shampoos, hair preparations such as conditioners and rinses, shaving preparations, especially aerosol shave preparation, skin conditioners and cleansing compositions, dishwashing detergent compositions, hand lotions, bubblebath compositions and the like.

The synthetic organic detergents or surface-active agents which may be employed in the compositions of the present invention may be selected from a wide variety of water-soluble anionic, nonionic or cationic surfactants such as are generally employed in aqueous cosmetic detergent or surfactant compositions which are meant to come into contact with the skin or hair.

Exemplary anionic materials are the water-soluble, straight and branched chain alkyl aryl sulfonates, particularly the alkyl benzene sulfonates, wherein the alkyl group contains from about 8 to 15 carbon atoms, the lower alkyl aryl or hydrotropic sulfonates such as sodium xylene sulfonate; the olefin sulfonates such as those produced by sulfonating a C to C straight chain alphaolefin; hydroxy C to C alkyl sulfonates; water-soluble alkene disulfonates containing from about 10 to 24 carbon atoms; the normal and secondary higher alkyl detergents, particularly those having about 8 to 15 carbon atoms in the alcohol residue such as lauryl or coconut fatty alcohol sulfate; sulfuric acid esters of polyhydric alcohols partially esterified With higher fatty acids such as coconut oil monoglyceride monosulfate, coconut ethanolamide sulfate, lauric acid amide or taurine and the like; the various soaps or salts of fatty acids containing from about 8 to 22, particularly 10 to 18, carbon atoms, such as the sodium, potassium, ammonium and lower alkanolamine, particularly mono-, diand triethanolamine salts of fatty acids such as stearic acid, oleic acid, coconut fatty acid, fatty acids derived from palm oil, soybean oil, tallow and the like. Particularly preferred anionic surfactants include the fatty alcohol and ether alcohol sulfates and the sodium salts of fatty acids containing from about 12 to 18 carbon atoms.

Exemplary nonionic detergents which may be employed in the compositions of the present invention are the polyalkylene oxide condensation products with a hydrophobic organic compound. The hydrophobic organic group usually contains from about 8 to 30 carbon atoms and is condensed with from about to 50 alkylene oxide groups such as ethylene oxide, propylene oxide, butylene oxide, and the like. Specific condensation products include the polyoxyethylene ethers of alkyl phenols wherein the alkyl group contains from about 6 to 12 carbon atoms and containing from about 8 to 18 mols of ethylene oxide per mol of said alkyl phenols; polyalkylene oxide ethers of fatty alcohols such as lauryl, myristyl, cetyl, stearyl and oleyl alcohols, and C to C oxo alcohols, which are condensed with from about 10 to 30 mols of ethylene oxide per mol of said alcohols; polyoxyalkylene esters of organic acids such as the higher fatty acids, rosin acids, tall oil acids and the like, said esters containing from about 12 to 30 mols of ethylene oxide and about 8 to 22 carbon atoms in the acyl group; polyalkylene oxides condensates with higher fatty acid amides, such as the higher fatty acid primary amides, monoand diethanolamides as well as condensates of higher fatty acid sulfonamides.

Further suitable nonionic surfactants are the higher fatty acid alkanolamides, such as the monoethanolamides, diethanolamides and isopropanolamides wherein the acyl radical has an average of from about 10 to 18 carbon atoms. Examples are coconut fatty acid, capric, lauric, oleic and myristic diethanolamides and the correspondnig monoethanolamides and isopropanolamides; the fatty tertiary amine oxides which may be represented by the general formula R R R N O wherein R represents C to C alkyl such as decyl, dodecyl, tetradecyl, octadecyl and the like and R and R represent methyl or ethyl.

Particularly preferred members of the above group of nonionic surfactants include the fatty acid alkanolamides and the polyoxyalkylene, particularly the ethylene oxide condensates thereof.

Exemplary cationic surfactants which may be employed in the compositions of the present invention are quaternary ammonium salts having long chain hydrophobic radicals such as C to C alkyl radicals as exemplified by l-methyl-l-higher alkyl amido-ethyl-Z-higher alkyl imidazolinum salts wherein the alkyl groups have 10 to 20 carbon atoms, ethoxylated long chain fatty quaternary ammonium compounds, higher alkyl benzyldimethylammonium salts, higher alkyl isoquinolinium salts, di (higher alkyl) dimethylammonium salts, and the like. The anion of the water-soluble quaternary ammonium compound is most usually a chloride or methosulfate, but other ions may be used such as bromide, phosphate, dialkyl phosphate or acetate ions.

The aforesaid anionic, cationic and nonionic surfactants are generally present in amounts ranging from about 5 to 85%, by weight, depending upon the particular cosmetic formulation prepared. Admixtures of the aforesaid may be employed so long as such admixtures are compatible and do not cause precipitation or otherwise adversely affect the stability of the system.

Exemplary cosmetic detergent compositions are shampoos containing water, 5-10% fatty amine oxide, 3-5% sodium fatty alcohol sulfate and about 3-5% of said C C dicarboxylic acid-fatty acid alkanolamide monoester salt; dishwashing liquids containing 1520% alkyl benzene sulfonate, 510% sulfated ethoxylated aliphatic alcohol, 310% hydrotropic sulfonate and from 5-10% of said C -C aliphatic dicarboxylic acid-fatty acid alkanolamide monoester salt; shampoo bars containing 60-70% mixed fatty acid soaps and 10-20% of said C -C aliphatic dicarboxylic acid-fatty acid alkanolamide monoester and the like.

Various supplemental materials may be added to the compositions of the present invention such as are generally employed in cosmetic preparations. Exemplary are additives such as lanolin, ethoxylated lanolin, glycerol and polyglycerols, lower alcohols such as ethanols, dyes, perfumes, antibacterial agents such as hexachlorophene, preservative agents such as formalin, sequestering agents such as water-soluble phosphate compounds and the like.

The aqueous-based cosmetic detergent compositions of the present invention possess a number of highly significant advantages. They exhibit excellent emolliency when applied to the skin as hand lotions, skin cleansing compositions, shaving creams, or in the form of dishwashing detergents. Emolliency refers to the desirable after-feel imparted to the skin and the conditioning and protective effects on the skin by the retention of natural greases or oils and the prevention and relief of dryness. Shampoos formulated in accordance with the present invention impart an observable improved manageability and luster t0 the hair and emolliency to the scalp, and in addition, they have a diminished degreasing effect and are non-irritating to the scalp and skin. Moreover, compositions such as shaving preparations also show excellent wetting and lathering properties and produce a soothing and non-irritating effect upon the skin. Generally the compositions of the present invention have the capacity to reduce and suppress the irritating tendency of conventional detergents commonly employed in detergent compositions. Even in hard water, wetting and lathering properties are not substantially diminished.

The invention is further illustrated by the following examples, which are not to be considered as limitative of its scope. Percentages are by weight.

EXAMPLE I A shampoo is prepared containing the following ingredients:

Percent (a) Sodium lauryl sulfate 7 (b) Lauric diethanolamide 3 (c) Triethanolamine salt of the monoester of succinic acid and coconut monoethanolamide 3 (d) Water 87 The above formulation is found to be high lathering even in hard water, and non-drying to the hair and scalp. It is observed that after use, the hair has good manageability and luster, and does not require the use of a hair conditioning rinse.

EXAMPLE II (d) Ethanol 10 (e) Ammonium salt of the monoester of lauric monoet-hanolamide and succinic acid 5 (f) Water 54 The above formulation is found not only to be nonirritating to the skin but produces an emollient effect on the skin after use. The identical composition, except for the ammonium lauric monoethanolamide monosuccinate is prepared for purposes of comparison and is found to produce a pronounced drying effect on the hands with little or no emollient effect on the skin perceptible.

EXAMPLE 'III A soap bar is prepared by combining the following ingredients:

This soap bar forms a lather with water which is quite copious, similar to that of a shampoo lather and has a desirable after-feel on the skin.

EMMPLE IV A shampoo is prepared by combining the following ingredients:

Percent (a) Coconut diethanolamide 5.0 (b) Sodium lauryl sulfate 9.0

(c) Triethanolamine dodecyl benzene sulfonate 8.0

(d) Perfume 0.4 (e) Monosodium phosphate 0.6 (f) Sodium salt of the monoester of malonic acid with oleic isopropanolamide 2.0 (g) Water 75 The product when applied to the hair significantly improves manageability with no drying eifect on the scalp.

EXAM'PLE V Example IV is repeated, except that for ingredient (f) there is employed the ammonium salt of the monoester of glutaric acid with lauric diethanolamide and equivalent results are obtained.

EXAMPLE VI A various emollient hand lotion is prepared by combining the following ingredients:

Percent (a) Lanolin 2.0 (b) Coconut diethanolamide 20.0 Sodium salt of the monoester of succinic acid with coconut butanolamide 5 .0 (d) Hexachlorop-hene 1.0 (e) Water 72 EXAMPLE VII A composition suitable as a skin-cleansing liquid or bubble-bath composition is prepared employing the following components:

A shampoo is prepared by combining the following ingredients:

Percent (a) Triethanolammonium coconut sulfate 8.0

(b) Sodium alkyl (C -C sulfate 7.0

(c) Sodium t-octylphenl sulfonate 6.0 ((1) Potassium salt of the monoester of succinic acid and lauric monoethanolamide 1.0

(e) Water 78 6 EXAMPLE IX A hairdressing composition is prepared by combining the following ingredients:

Percent (a) Polyoxyethylene ether of lauryl alcohol having 23 oxyethylene units 5.0 (b) Lauric diethanolamide 6.0 (c) Lanolin 2.0 (d) Sodium salt of the monoester of succinic acid and coconut monoethanolamide 5.0 (e) Glycerine 10.0 (f) Water 72 EXAMPLE X A shaving cream suitable for use in aerosol-type dispensers is prepared by combining the following ingredients:

Percent (a) Glycerol 10.0 (b) Triethanolamine 4.0 (c) Stearic acid 4.5 (d) Coconut fatty acids 1.5 (e) Glyceryl monostearate 5.0

(f) Triethanolamine salt of coconut monoethanolamide succinic acid monoester 3.0 (g) Water 66.0 (h) Propellent (dichlorodifluoromethane-dichlorodifluoroethane mixture) 6.0

EXAMPLE XI An emollient skin cream is prepared by combining the following ingredients:

Percent (a) Glyceryl monostearate 10.0 (b) Glycerol 15.0 (c) Cetyl trimethyl ammonium chloride 0.2

(d) Sodium salt of the monoester of succinic acid and coconut monoethanolamide (e) Water 69.8

EXAMPLE XII A shampoo is prepared by combining the following ingredients and is observed by the user to impart a greater What is claimed is:

1. An aqueous-based cosmetic detergent composition which consists essentially of (a) from about 10% to 90%, by weight, of water; (b) from about 1% to 20%, by Weight, of a member of the group consisting of ammonium, C -C alkanolamine and alkali metal salts of monoesters of C -C saturated, unsubstituted, aliphatic dicarboxylic acids with fatty acid monoand di-alkanolamides wherein the alkanol portion contains up to 8 carbon atoms; and (c) from 5% to by weight, of a member of the group consisting of synthetic anionic, nonionic and cationic organic detergents and compatible mixtures of same with the proviso that said (0) ingredient is distinct from said (b) ingredient.

2. A composition according to claim 1 wherein said aliphatic dicarboxylic acid is succinic acid.

3. A compostion according to claim 1 wherein said fatty acid alkanolamide is a monoalkanolamide.

4. A composition according to claim 1 wherein said fatty acid contains from 10 to 18 carbon atoms.

5. A composition according to claim 1 wherein said salt is a sodium salt.

6. A composition according to claim 1 wherein said salts of said monoesters are present in an amount of from about 3% to about 10% by weight.

7. A composition according to claim 1 wherein said synthetic organic detergent is a fatty alcohol sulfate.

8. A composition according to claim 1 wherein said synthetic organic detergent is a member of the group consisting of fatty acid salts, fatty acid soaps and mixtures thereof.

9. A composition according to claim 1 wherein said synthetic organic detergent is a fatty acid alkanolamide.

10. A composition according to claim 6 wherein said monoester salt is the sodium salt of the monoester of succinic acid and coconut monoethanolamide.

monoester salt is the triethanolamine salt of the monoester of succinic acid and lauric monoethanolamide.

References Cited UNITED STATES PATENTS 2,173,448 9/1939 Katzman et al. 260404 2,733,212 1/ 1956 Epstein et a] 252-117 2,343,431 3/ 1944 Wells et a1 260-404 X 10 RICHARD D. LOVERING, Primary Examiner U.S. Cl. X.R.

252-90, 117, 134, 356, 527, 548, DIG. 5, DIG. 13;

11. A composition according to claim 6 wherein said 15 424-47 73

Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3996148 *Jul 25, 1975Dec 7, 1976Pierre FuseyFrom a carboxylic diacid and a hydrocarbon or hydroxy amine
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Classifications
U.S. Classification510/426, 510/126, 424/70.19, 510/135, 516/DIG.600, 510/159, 510/152, 424/73, 510/237, 424/47, 510/125, 510/433, 516/69, 510/437
International ClassificationC11D10/04, A61Q9/02, C11D1/88, C11D1/29, C11D1/20, A61K8/37, A61Q19/10, C11D1/00, A61Q5/02, C11D1/52, C11D1/14
Cooperative ClassificationA61Q9/02, A61Q5/02, C11D1/523, C11D1/20, C11D1/88, A61Q19/10, C11D10/04, A61K8/37, Y10S516/06, C11D1/14, C11D1/29
European ClassificationA61Q19/10, A61Q5/02, C11D10/04, C11D1/88, A61Q9/02, A61K8/37