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Publication numberUS3697655 A
Publication typeGrant
Publication dateOct 10, 1972
Filing dateOct 28, 1969
Priority dateDec 11, 1968
Also published asDE1962238A1
Publication numberUS 3697655 A, US 3697655A, US-A-3697655, US3697655 A, US3697655A
InventorsHerman Berenson, Robert Alden Stonier, Eugene Everett Wiese
Original AssigneeAmerican Cyanamid Co
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Germicidal detergent compositions in controlling dandruff
US 3697655 A
Abstract  available in
Previous page
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Claims  available in
Description  (OCR text may contain errors)

United States Patent Berenson et al.

GERMICIDAL DETERGENT COMPQSITIONS IN CONTROLLING DANDRUFF Inventors: Herman Berenson, Trenton; Robert Alden Stonier, Glen Rock; Eugene Everett Wiese, Wyckoff, all of NJ.

American Cyanamid Company, Stamford, Conn.

Filed: Oct. 28, 1969 Appl. No.: 871,960

Related US. Application Data Continuation-impart of Ser. No. 783,123, Dec. 1 l, 1968, abandoned.


US. Cl. ..424/204, 424/316, 424/319 Int. Cl. ..A6lk 27/00 Field of Search ..424/204, 319, 316

References Cited UNITED STATES PATENTS l/ 1968 Berenson et al. ..424/ 195 4/1970 Berenson et al. ..424/195 4/1949 lsbell ..260/534 51 Oct. 10, 1972 3,093,591 5/1963 Freese ..252/107 3,281,365 10/ 1966 Moedritzer ..252/106 3,317,430 5/1967 Priestly et al. ..252/152 Primary Examiner-Stanley .l. Friedman V Attorney-John M. Miele ABSTRACT Compositions, generally useful for germicidal detergent applications, comprising a mixture of (a) an amphoteric surfactant such as N-coco B-amino propionic acid or a fatty (coco) amido alkyl betaine and (b) an organophosphorus salt of the formula:

6 Claims, No Drawings GERMICIDAL DETERGENT COMPOSITIONS IN CONTROLLING DANDRUFF This application is a continuationin-part of Ser. No. 783,123, filed Dec. 11, 1968 now abandoned.

This invention relates (l) to germicidal detergent compositions useful generally in the treatment of the skin and hair, (2) to methods of controlling dandruff, and (3) to antidandruff compositions.

BACKGROUND A. Germicidal Detergent Compositions While certain compounds such as quaternary ammonium salts are known to be surface active as well as germicidal, the surface activity falls short, at use concentrations which are economical, of promoting the detergency required in products for treatment of the hair and skin such as shampoos, rinses, surgical scrub compositions, cosmetic creams, anti-perspirants, and other cosmetic and grooming compositions where detergency coupled with germicidal activity is important. The improved detergency therefore is generally provided by combining a known detergent with a known germicide.

The selection of a detergent and germicide for combination in compositions effective for the intended purpose is not a simple matter, however. Thus, the numerous properties required in a germicide intended for contact with the skin and hair drastically limit the field of choice. Among these properties may be included inherent microbial effectiveness (broad spectrum antimicrobial activity particularly against bacteria, yeasts and molds or fungi known to thrive on the mammalian body); substantivity (sorbability) or tendency to be deposited on the skin and hair (including the scalp); microbiological availability (elution rate) while on the skin and hair including the scalp; activity at economical use concentrations; substantially no harmful effect to the skin or hair or disagreeable odor; stability (no substantial loss of activity or tendency to separate from other ingredients of formulations while in storage); no substantial reactivity with the metal linings of vessels used in preparation or packaging; and compatibility with the detergent as well as other cosmetic ingredients normally included in germicidal detergent compositions.

Likewise, the choice of detergent is critically limited not only by the requirements of the environment being treated but also by the germicide selected for the compositions. Thus, in addition to the requirements of no harmful effect on skin or hair at use concentrations, no disagreeable odor, and effective detergency particularly as accompanied by foamability, the detergent must not substantially inactivate the germicide and must be compatible with the germicide such that the combination, in the conventional cosmetic vehicles, and over the pH range desirable for cosmetic use, remains stable during a storage period. To the foregoing may be added the further important requirement that the germicidal agent not lose its activity by reason of drying out on the skin or hair. While certain genuicides are known to be effective in combination with detergents for use on the skin and hair, it has been observed that these germicides rapidly dry out, thereby losing their germicidal activity.

Given all the foregoing properties in the detergent and germicide as well as in the combination, the consumer has preference for a composition which is clear or transparent over a composition which is opaque. The reason for this resides not only in the high degree of quality ascribed to clear or transparent compositions but also in the technical advantage that the residue on the skin or hair of a clear or transparent composition is substantially non-detectable whereas the residue of an opaque composition is undesirably apparent, in some instances even to the extent of modifying the color and texture of the hair.

B. Antidrandruff Compositions When it is proposed to use a known germicide for the control of dandruff whether on the animal or human scalp, but particularly the latter, certain of the foregoing requirements as well as others become especially critical as compared with gennicidal-detergent uses generally. The reason for this concerns the nature of dandruff" and the state of the dandruff control art. At the present time it is believed that a dandruff condition involves not a simple, identifiable disease but several factors in which a diseased state may or may not be important. For example, although some investigators have noted the presence of Staphylococcus aureus and Pityrosporum ovale skin bacteria along with the oily, dead scale usually called dandruff, absolute statements that these particular organisms are the sole cause of dandruff have been disproved since these bacteria have been found on the majority of scalps, whether dandruff scale is present or not. See Antidandruff Preparations, H. J. Spoor, in Cosmetics, Science and Technology, Interscience, New York, 1957, pp. 641- 650. Consequently, the knowledge that a certain compound (such as that described in U.S. Pat. No. 3,364,107) controls broad classes of microbes specifically including S. aureus and P. ovale, is wholly insufficient to lead one to conclude that the compound would be effective in combatting a dandruff condition.

Dandruff is therefore a complex condition, involving the accumulation of sloughed off epidermal scale, oily secretion and acquired soil. It is known that this accumulation offers an ideal nutrient medium for many types of microorganisms, including those already mentioned, giving rise to infections such as seborrhea. It is believed that growth of these microbes promotes or is accompanied by itching, hair loss and the unpleasant appearance associated with increased desquamation of epidermal cells. Acceptable dandruff control therefore requires at least the following properties in a material chosen for this use in addition to those properties set forth above for general germicidal-detergent use: antimicrobial effect at least against the microorganisms commonly associated with dandruff; ability to reduce scaling and to relieve itching; and water solubility and cosmetic vehicle compability sufficient to permit preparation of aqueous formulations and cosmetic formulations in which a major portion of the vehicle is non-aqueous.

SUMMARY OF THE INVENTION An object of this invention is to provide a germicidal detergent composition or mixture having the foregoing properties, especially the properties of substantivity to the skin and hair, resistance of the germicidal ingredient to drying out when the composition is applied in conventional cosmetic vehicles, and clarity. A further object is to provide a method of combatting and controlling dandruff conditions in animal and human hair, and compositions for this purpose. These and other objects, features and advantages are further detailed in the following description.

Accordingly, the composition of the present invention which is useful for general germicidal-detergent applications contains as essential ingredients (a) certain amphoteric surfactants and (b) a certain organo phosphorus salt having germicidal properties. Ingredient (a) provides the required detergency in the composition. For dandruff control, ingredient (b) may be employed with a non-aqueous cosmetically acceptable vehicle without ingredient (a) and without water, if desired; however, the preferred composition even for antidandruff use is the composition comprising (a) and (b) in an aqueous medium.

DETAILED DESCRIPTION The organo phosphorus salt germicidal agents are known compounds and may be represented by formula wherein R, R and R independently are alkyl (C,C, phenyl, or hydroxyalkyl (C,C x is 6-14 and X is an anion.

The anion represented by X includes halides such as chloride, bromide, and iodide; and perchlorate, nitrate, sulfate, ROSO ROSO-, RSO where R is alkyl or aryl such as methyl, ethyl, propyl or butyl, and phenyl. Those salts are preferred which enhance the water solubility of the compounds and of these the halides are preferred. Hydroxyalkyl includes both straight and branch chain alkyl such as 3-hydroxypropyl, 3-hydroxybutyl, and the like.

Illustrative of the salts are the following:

1 l O-decamethylenebis [diphenylethylphosphonium bromide] l l -decamethylenebis[ tributylphosphonium bromide 1; l l O-decamethylenebis[ diethylphenylphosphonium bromide];


1 ,l0-decamethylenebis[triphenylphosphonium bromide]; 1 l 6-hexadecamethylenebis[triphenylphosphonium chloride]. The last two compounds in the foregoing list are preferred;

The amphoteric surfactants are selected from compounds of formulas (II) and (III):

(II) RNHm(CH:CHaCO OM) RC ONH(CH,)INCH2C O OM ln formulas ll and Ill, R is alkyl of at least 8 carbon atoms and M is hydrogen or a cation. In formula I], m is 0 or 1, n is l or 2, and the sum ofn and m is 2. Alkyl in the definition of R is the fatty residue of a fatty acid (or mixture of fatty acids) employed in preparing the primary amine reactant which, in turn, is reacted with acrylic monomers in forming the amphoteric product. While the carbon content of R may vary up to about 22 carbon atoms, the preferred range is about 12 to 14 carbon atoms since this range provides better'surface active properties particularly with respect to foamability. Typical cations include the water solubilizing alkali and alkaline earth metals and amines such as sodium potassium, barium, ammonia, and triethylamine.

Typical of amphoteric surfactants of formula ll, useful singly or in admixture, are the following:

Sodium N-coco B-aminopropionate N-coco B-amino propionic acid N-lauryl/rnyris'tyl B-amino propionic acid Disodium N-tallow B-iminodipropionate Disodium N-lauryl B-iminodipropionate Partial sodium salt of N-lauryl fi-iminodipropionic acid The amphoteric surfactants of formulas ll and Ill above are known compounds as described, for example, in U.S. Pat. Nos. 2,619,467, 2,816,920 and 2,993,071. The formula III compounds are also known as fatty (coco) amido alkyl betaines. Of the foregoing sufactants, N-lauryl/myristyl B-arnino propionic acid and the fatty (coco) amido alkyl betaines provide the best results and therefore are the preferred surfactants, alone or in admixture.

Although US. Pat. No. 3,364,107 discloses combinations of the above organo phosphorus salts with commercial anionic synthetic detergents, the use therein is in the laundering of fabrics where the problem of compatibility and stability of the compositions is not pronounced. In contrast, the present environment of use on skin or hair as well as acceptability of the liquid formulation to the consumer, require close attention to compatibility and stability of formulations prepared with the germicide and detergent. Thus, it has been found that the commercial anionic synthetic detergents generally are incompatible with the organo phosphorus salts, presumably due to the cationic character of the organo phosphorus salt. The use of nonionic surfactants alone, although compatible with the organo phosphorus salt, is excluded by reason of their poor lathering quality and tendency to reduce the substantivity of the organo phosphorus germicide to the skin and hair. However, for some specialized uses, minor amounts of cationic surfactants or nonionic surfactants, each alone or in admixture, may be employed with the amphoteric surfactants provided they do not substantially reduce the essential characteristics of the composition. While cationic surfactants are compatible with the organo phosphorus germicide, such surfactants tend to be irritating to the skin and are not as substantive. However, cationic surfactants may be included in the compositions of the present invention in minor amounts provided they do not seriously detract from the essential characteristics of the compositions.

The amphoteric surfactants of the formulas II and Ill above have been selected over other well known amphoteric surfactants, such as the amine oxides, other betaines, and cycloimidates, since it has been observed that these other amphoteric surfactants tend to reduce antibacterial activity with the germicide at the pH range of use, tend to reduce the activity of the germicide, or provide inadequate lathering. The pH range desirable for cosmetic formulation is about 6.5 to about 8.0. It is a surprising result that, although the amphoteric surfactants of the invention become anionic above their isolectric points (which in the case of the formula II compounds range from about pH 2.1 to pH 4.7), no substantial incompatibility with the cationic organo phosphorus salt is observed over the pH range for cosmetic applications.

The organo phosphorus salt gerrnicides of the present invention may be employed in amounts of from about 0.05 to about 25%, based on the weight of the amphoteric surfactant, and in amounts of from about 0.01 to about 20%, based on the weight of the total composition, including diluents and other additives. The preferred ranges are from about from 2.5 to about based on the weight of the amphoteric surfactant and from about 0.5 to about 2.0%, based on the weight of the total composition, including diluents and other additives. The amphoteric surfactant is employed in amounts of from about 0.1 to about 25%, based on the total weight of the composition, preferably from about 0.5 to about 15%, same basis. When the surfactant comprises a mixture of the N-coco-B-amino propionic acid (or propionate) of formula II and the betaine of formula III, these surfactants may vary in relative proportions from l-99% to 99l%, but preferably are employed in the range of 10-40% by weight of the formula ll compounds to 9060% by weight of the formula Ill compounds.

To the essential combination of amphoteric surfactant and germicidal compound may be added a wide variety of ingredients conventional in the skin and hair cosmetic arts. For example, it is common to employ a diluent or cosmetically acceptable carrier such as water, a water miscible alcohol such as ethyl alcohol or isopropyl alcohol, and the like. Other well known ingredients include preservatives, such as formalin; dyes such as those listed by the Food and Drug Administration; perfumes; buffering agents for pH control; and various conditioning and grooming agents such as lanolin and lanolin derivatives, fatty alcohols or fatty esters, ethoxylated polyhydroxy esters, cholesterol, coconut oil, mineral oil and the like.

The compositions of the invention are formed in the conventional manner by mixing the amphoteric surfactant and organo phosphorus germicide alone or in the presence of a diluent which is cosmetically acceptable, or also with other cosmetic ingredients such as described above. When antidandruff effect is intended, the germicidal ingredient (b) may be dissolved in water to the extent of about 0.01 to 5.0% and applied as a rinse to the affected area. Preferably, however, the germicidal ingredient is used in admixture with surfactant (a), particularly in combination with cosmetic ingredients conventionally employed in shampoos, lotions, and the like.

The following examples are intended as further illustration of the invention but are not necessarily limitative except as set forth in the claims. All parts and percentages are by weight unless otherwise indicated.

EXAMPLE 1 The formulations shown in Table l below are prepared and subjected to a hair protection test with the results shown in Table I. The surfactants of the formulations are identified as follows:

Surfactant Name Alkyl (C coco fatty) ammonium sulfonic acid betaine Alkyl (C coco fatty) carboxylic betaine N-coco fl-amino propionic acid /30 lauric/myristic diethanolamide l:l mixture of alkyl dimethyl benzyl ammonium chloride (50%) and alkyl isoquinolinium bromide 6 Nonylphenol/ethylene oxide condensate, mol

ratio 129.5

MJ UN Hair Protection Test Human hair swatches (20 strands, 2 inches long, knotted together at one end) are immersed in a 1:1 dilution of the composition containing the germicidal ingredient for at least two minutes. The treated hair is rinsed twice in 100 ml. aliquots of sterile tap water. The hair swatches are then dried for two minutes under an Oster hair blower drier. The swatches are placed on the appropriate agar and overlayed with ml. of the same agar containing one loopful (4 mm. CD) of the appropriate test organism per ml. of agar. Plates are incubated at 37 C. until growth appears and zones of inhibition can be read. The compositions are rated as active or inactive according to whether growth zones are not or are observed in substantial quantity, respectively. inconclusive activity is (i).

TABLE I Formulations ingredients, by weight A B C D E F Surfactant 1 44.4 Surfactant 2 44.4 44,4 Surfactant 3 44.4 44.4 44.4 Sequestrant 1.0 1.0 1.0 1.0 1.0 1.0 Ethanol SD-40 8.0 8.0 8.0 8.0 8.0 8.0 Surfactant 4 5.0 5.0 5.0 5.0 5.0 Germicide 1.0 1.0 2.0 2.0 2.0 Surfactant 5 1.0

qs to qs to qs to qs to qs to qs to Water 100 100 100 100 I00 100 Hair Protection Test Test Organism A B C D E F S. aureus S. epidermis C. parapsiloris -l C. mycoderma P. ovale R. mucilaginosn Compositions, C, D and E, representative of the invention, exhibit not only superior germicidal activity but also superior lathering and substantivity to the hair as compared with the other compoistions which contain different amphoteric surfactants. Substantivity is proved by reason of the germicidal activity persisting through repeated rinsings and drying.

EXAMPLE 2 Substantially as described in Example 1, the formulations shown in Table 11 below are prepared and tested, with the results shown in Table II. The surfactants and germicide are the same as in Example 1. TEA-L--SO is triethanolamine lauryl sulfate and the thickener is hydroxy propyl methyl cellulose 1%).

Hair Protection Test Test Organism A B C D E S. aureus P. ovale I C. parapsilosis i It will be seen from Table II that only composition B, representative of the invention, provided activity against all three microbial species. Composition B was also superior to the others in substantivity and detergency (lathering).

EXAMPLE 3 Substantially as described in the foregoing examples, the formulations shown below in Table III are prepared and tested, with the results also shown in Table III. The

surfactants, sequestrant and germicide are the same as in Example 1. Composition C represents a formulation with increased viscosity and in Composition D and pH has been lowered by addition of an acid. These results show that Composition A, representative of the invention, is superior to the others in that it controlled all four test organisms including P. ovale, a species generally found in the same environment with dandruff.

TABLE III Formulations Ingredients (Wt. A B C D Surfactant 3 44.4 Surfactant 2 44.4 44.4 44.4 ant 1.0 1.0 1.0 1.0 Ethanol SD-40 8.0 8.0 8.0 8.0 Surfactant 4 5.0 5.0 10.0 5.0 Gennicide 1.0 1.0 L0 1.0 NaCl 2.0 Citric Acid 0.8 Water qs qs qs qs Hair Protection Test Test Organism A B C D R. Mucilaginosa C. M yeoderma P. Ovale S. Aureus EXAMPLE 4 Table IV below illustrates other formulations in which the surfactants, sequestrant and germicide are the same as in Example 1 except the following:

Surfactant 7: alkyl sulfate salt of lauroylcycloimidiniuml ethoxy ethionic acid-2 ethionic where R is C derived from coco fatty acids. Available from Goldschmidt Chemical Company.

All of the formulations contain 20% active amphoteric and formulation E is representative of the invention. Table IV also shows results of hair protection tests conducted substantially as described in Example I. It will be noted that only formulation E is active against both organisms although all the formulations contain an amphoteric surfactant and the same germicide. The germicidal activity is therefore the cooperative effect of both the germicide and the specific amphoteric surfactant.

Table V below demonstrates that other surfactants (the cationic surfactant 9 of formulation A and the amine oxide amphoteric Surfactant 10 of formulation C) may be added to the basic combination of germicide and amphoteric surfactant without adversely affecting the hair protection afforded by the basic combination. It will be noted that formulations B and D, lacking the germicide, give negative results. The hair protection test, the germicide and Surfactant 3 are the same as in Example I and the other ingredients are as follows:

Surfactant l: Alkyl (50% C14, 40% C C18) di sthxl m! emanate ees a fia These results are significant since it is often desirable to add such other materials (representative of conditioners, softeners, preservatives, gennistats, and the like) when formulating hair treating compositions which incorporate the basic composition of the invention. Compatibility and germicidal-detergent efficacy is not thereby sacrificed.

TABLE V Formulations Ingredients (Wt. A B C D Surfactant 3 44.4 44.4 44.4 44.4 Surfactant 9 3.0 3.0 3.0 3.0 Surfactant 10 0.5 0.5 Germicide l.0 1.0

qs to qs to qs to qs to Water 100 I00 100 I00 Hair Protection Test Test Organism A B C D S. Aureus P. Ovale C. Albicans The compatibility of the germicides and amphoteric surfactants of the invention (formulas I, II, and III above) over the range of pH useful in the treatment of the hair and skin (pH 6.5 8.0) is a highly surprising and beneficial result. Thus, although these amphoteric surfactants become anionic abovepH 3.54.7 (upper limit of isolectric range), they nevertheless remain compatible with the organo phosphorus germicide, which is cationic. The formulations thus remain substantive, gerrnicidally active, and stable despite pH conditions under which incompatibility would normally be expected. Formulations of the foregoing examples illustrative of this anomalous result are formulation C of Table I, formulation A of Table III, formulation E 'of Table IV (each pH 7.5-7.6) and formulation B of Table II (pH 6-8) EXAMPLE 6 Substantially as described in the foregoing Examples, the following preferred formulation of Table VI is prepared (in which the germicide is the same as in Example l) and tested, the results also being indicated in the Table.

TABLE VI Formulation Hair Protection Test Ingredients Wt. Test Organism Germicide 2.0 S. aureus Surfactant 8 60.0 C. parapsilaris N-lauryl/myristyl P. avale B-amino propionic acid 5 0 R. mucilaginosa Surfactant 4 8.0 C. albicans NaCl 4.0 Sequestrant l.O Propylene glycol 5 0 Citric to pH 7.5-8.0 0.4 Water qs to I00 EXAMPLES 7-l 3 The following formulations illustrate various products incorporating the germicidal detergent composition of the invention. The germicide is that of Example l.

7. HAND 8L BODY LOTION Germicide 0.5 Surfactant 3 10.0 Glyceryl Monostearate 3.0 Isopropyl Palmitate-Myristate 5.0 Lanolin 2.0 Propylene Glycol 5.0 Water 74.5

8. MEDICATED CREME RINSE Germicide 1.0 Surfactant 3 5.0 Stearyl-Dimethyl Benzyl 5.0

Ammonium Chloride Polyoxyethylene Glycol 3.0

400 Disterate Water 84.0

9. HAIR DRESSING Germicide 0.25 Ethyl Alcohol SD-40 40.00

Surfactant 3 2.50 Water 57.25

10. GERMICIDAL CLEANER Germicide 0.5 Surfactant 3 5.0 Ethoxylated Iso-Octyl Phenol 5.0 Coconut Diethanolamide 5.0 Propylene Glycol 10.0 Tetrapotassium Pyrophosphate 10.0 Water 64.5

1 1. DIAPER DEODORANT Germicide 1.0 Surfactant 3 5.0 Propylene Glycol 5.0 Water 89.0

12. ATHLETES FOOT LOTION Germicide 0.25 Surfactant 3 3.00 Boric Acid 0.10 Alcohol SD-40 15.0 Acetone 10.0 Water 71.65

13. SURGICAL SCRUB Germicide 1.0 Ethoxylated Nonyl Phenol 10.0 Surfactant 3 25.0 Coconut Diethanolamide 5.0 Alcohol SD-40 10.0 \Vater 49.0

EXAMPLE 14 By substituting 1 ,16-hexadecamethylenebis[triphenylphosphon-ium chloride] for l ,10- decamethylenebis[triphenylphosphonium bromide] in Examples 1-13, substantially equivalent formulations are obtained.

EXAMPLE 15 This example demonstrates the antidandruff utility of the organophosphorus salts of the invention.

A total of 258 adult humans arranged in five groups of approximately 50 each were formed. Each subject in an initial qualifying examination had been judged by a professional dermatologist to have severe dandruff as defined by a score of 6, 7 or 8 determined by totalling the values from the following scale where the values resulted from two inspections of the scalp, the first for loose dandruff (dandruff on or in the hair) and the second for adherent dandruff (dandruff still attached to the scalp):

4 very severe dandruff 3 severe dandruff 2 moderate dandruff 1 mild dandruff absent dandruff The total value of 6, 7 or 8 excluded only those subjects whose total resulted from a combination of 4 (loose dandruff inspection) and 2 (adherent dandruff inspection. Also excluded were subjects having identifiable dermatological conditions, such as psoriasis. The five groups were so constituted as to equalize all variables, statistically.

The subjects were instructed to shampoo once weekly, always on the same day of the week, with an assigned test product. The five test products (A-F) are described below. Test products B through E are applied by the subjects without prior treatment of the hair but application of test products A (a rinse) was preceded by shampooing with a commercial shampoo not containing an antidandruff agent. The subjects then were required to report for examination 5 days after the shampooing, 2, 4, 6 and 8 weeks after the initial, qualifying examination. At each examination the dermatologist graded both loose and adherent dandruff, the condition of each subjects scalp (dry, oily or normal), and the degree of itching. In addition, at least 25 subjects from each of the groups using test products C and D were examined for safety of the product at the qualifying examination and then after the eight weeks of use of the test products. The safety tests were designed to measure adverse reactions and were based on a complete blood count, including: Red Blood Cell count, White Blood Cell Count, Hemoglobin, I-Iematocrit, Differential White Blood Cell Count, Appearance of red blood cells, Erythrocyte Sedimentation Rate, Serum Glutamic Oxalacetic Transaminase, Blood Urea Nitrogen, Serum Bilirubin, Thymol Turbidity and Routine and Microscopic Urinalysis.

The test products, a different one of which was assigned to each of the five groups of subjects, were as follows:

Test Product E: a commercially available lotion shampoo containing 2% by weight of zinc pyridinethione as the anti-dandruff ingredient.

Table VIII below establishes the magnitude of effectiveness of the five test products in terms of an approximation of the quantity of dandruff at the start and at the end of the study. The Table also shows the percent reduction in dandruff throughout the eight weeks of the test. From a statistical standpoint, the results establish that all of the test products were highly effective in combatting dandruff.

TABLE VIII I: Reduction, Test No. of start to week:

Group Product Subjects Start End 2 4 6 8 Table IX below shows that hair and scalp condition, in terms of dryness, normalcy or oiliness, was improved by each test product, test products C and D being the most effective.

TABLE IX Condition of Scalp and Hair Start Finish X1 Group Product Dry Normal Oily Dry Normal Oily l A 10.0 48.0 42.0 10.0 60.0 30.0 2 B 7.4 53.7 38.9 14.8 57.4 27.8 3 C ll 1 42.6 46.3 9.3 57.4 33.3 4 D 34.0 54.7 7.5 47.2 45.3 5 E 48.9 31.9 17.0 55.3 27.7

Table X below shows that itching was relieved in most cases by each test product, those products containing at least 1% of the germicide being the most effective.

With respect to the safety tests, which were conducted on subjects in the groups using test products C and D, no adverse reactions were noted.

Although the clinical studies reported above relate to use of the compositions of the invention for the control tion of scales and oily debris on the skin or hide generally described as dandruff. Accordingly, the invention is not limited to the treatment of human dandruff but includes treatment of such conditions in the hairor fur-bearing lower animals as well.

It should be apparent from the foregoing description that although it is preferred to employ the specified amphoteric surfactants with the organophosphorus salts when treating dandruff conditions, as in shampoos or lotions, these surfactants are not critical for dandruff control. Accordingly, for this specific use the organophosphorus salts may be dispersed in any cosmetically acceptable vehicle, including water alone, ethyl or isopropyl alcohol alone, alcohol-water mixtures, oil-inwater or water-in-oil emulsions and the like, and applied in the conventional manner as shampoos, lotions,

creams, pastes, gels, ointments, and the like. Moreover, while certain relative proportions and amounts based on total compositions have been described, such proportions and amounts may vary widely, depending on the viscosity or cosmetic effects desired as well as level of germicidal activity.

We claim:

1. A method of controlling dandruff which comprises applying to a region afflicted with dandruff an effective amount of a composition which comprises effective amounts I a. an amphoteric compound selected from the group consisting of w RNH (CH3CHgCOOM) and RCOHN(CH2)3NCH:COOM

wherein R is alkyl of at least eight carbon atoms, M is hydrogen or a cation selected from the group consisting of water solubilizing alkali and alkaline earth metals and amines, m is 0 or 1, n is l or 2, and the sum of n and m is 2, and

b. an organophosphorus compound of the formula wherein R, R and R independently are alkyl (C C phenyl or hydroxyalkyl (C -C x is 6-14 and X is an anion selected from the group consisting of halides, perchlorates, nitrates, sulfates, R OSO R 080, and RSO where R is alkyl or aryl.

2. The method of claim 1 wherein said organophosphorus compound is applied as an aqueous mixture in which (a) is N-coco-B-amino propionic acid, N-lauryl/myristyl ,B-amino propionic acid, or fatty (coco) amido alkyl betaine.

3. The method of claim 1 wherein said organophosphorus compound is l l 0- decamethylenebis[triphenylphosphonium bromide].

4. The method of claim 1 wherein said organophosphorus compound is applied as an aqueousalcoholic mixture.

5. The method of claim 3 wherein said organophosphorus is applied as an aqueous mixture in which (a) is a mixture of N-lauryl/myristyl B-amino propionic acid and fatty (coco) amido alkyl betaine.

6. The method of claim 5 wherein said organophosphorus compound is l l 0- decamethylenebisI triphenyl phosphonium

Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US4062976 *Dec 18, 1975Dec 13, 1977Michaels Edwin BAntimicrobial compositions employing certain substituted alanines and certain t-amine oxides
US4075350 *Dec 18, 1975Feb 21, 1978Michaels Edwin BAntimicrobial compositions employing certain betaines and certain amine oxides
US4957948 *Sep 9, 1988Sep 18, 1990Interface, Inc.Biocidal protective coating for heat exchanger coils
US5635192 *Jun 6, 1995Jun 3, 1997Interface, Inc.Biocidal polymeric coating for heat exchanger coils
US5639464 *Jun 6, 1995Jun 17, 1997Interface, Inc.Biocidal polymeric coating for heat exchanger coils
U.S. Classification514/107, 514/108, 514/852
International ClassificationA61K8/55, A61Q15/00, A61K8/44, A61Q3/00, A61Q5/00, C11D1/88, A61Q17/00
Cooperative ClassificationA61Q17/005, A61Q5/006, A61K8/55, A61Q19/00, A61Q15/00, A61K8/44, A61K8/442, Y10S514/852, C11D1/88
European ClassificationC11D1/88, A61K8/55, A61K8/44, A61K8/44D, A61Q5/00F