Imparting deodorizing and antibacterial effects to the hair with bifunctional antioxidants
United States Patent 3903257
Cosmetic compositions for hair containing a compound of the formula (1) ##SPC1## Wherein n is 0 or 1, R1 is an aliphatic hydrocarbon radical having 8 to 14 carbon atoms or a tertiary butyl radical and R2 and R3 each are hydrogen or alkyl or hydroxyalkyl having 1 or 2 carbon atoms, with the proviso that at least one of R2 and R3 is said alkyl or hydroxyalkyl.
US Patent References:
Halogenated bis-(hydroxy-aryl)-oxides
Muth et al. - October 1933 - 1932595
Prevention of plant growth with arylic sulfides
Schlesinger - November 1954 - 2695224
Compositions for treatment of the hair
Zviak - November 1963 - 3109777
Germicidal alkylhalodiphenyl oxide sulfonate compositions
Steinhauer et al. - April 1966 - 3245914
Antiseptic detergent compositions
Noel et al. - June 1966 - 3256201
Halogenated bis-(hydroxy-aryl)-oxides
Muth et al. - October 1933 - 1932595
Prevention of plant growth with arylic sulfides
Schlesinger - November 1954 - 2695224
Compositions for treatment of the hair
Zviak - November 1963 - 3109777
Germicidal alkylhalodiphenyl oxide sulfonate compositions
Steinhauer et al. - April 1966 - 3245914
Antiseptic detergent compositions
Noel et al. - June 1966 - 3256201
Inventors:
Arai, Haruhiko (Narashino, JA)
Mino, Junryo (Kamagaya, JA)
Inoue, Shigeo (Tokyo, JA)
Mino, Junryo (Kamagaya, JA)
Inoue, Shigeo (Tokyo, JA)
Application Number:
05/400257
Publication Date:
09/02/1975
Filing Date:
09/24/1973
View Patent Images:
Export Citation:
Assignee:
Kao Soap Co., Ltd. (Tokyo, JA)
Primary Class:
Other Classes:
510/119, 424/DIG.004, 510/492, 510/386, 514/712
International Classes:
A61K7/06; A61K7/32; A01N9/12
Field of Search:
424/DIG.4,337,65,70 260/69R 252/106,107
US Patent References:
| 3574853 | April 1971 | Barnhart |
Primary Examiner:
Meyers, Albert T.
Assistant Examiner:
Clarke, Vera C.
Attorney, Agent or Firm:
Woodhams, Blanchard And Flynn
Claims:
The embodiments of the invention in which an exclusive property of privilege is claimed are defined as follows
1. A method for imparting a durable antibacterial and deodorizing effect to the hair and skin of the head of a human being, which comprises topically applying thereto an effective amount of a compound of the formula ##SPC3##
2. The method according to claim 1, in which a hair shampoo, a hair rinse or a hairgrooming aid containing from about 0.001 to about 2.0 percent by weight of said compound is applied.
1. A method for imparting a durable antibacterial and deodorizing effect to the hair and skin of the head of a human being, which comprises topically applying thereto an effective amount of a compound of the formula ##SPC3##
2. The method according to claim 1, in which a hair shampoo, a hair rinse or a hairgrooming aid containing from about 0.001 to about 2.0 percent by weight of said compound is applied.
Description:
BACKGROUND OF THE INVENTION
FIELD OF THE INVENTION
This invention relates to cosmetic compositions for hair, more specifically, shampoos, hair-rinsing agents, hair lotions, hair oils, hair creams and pomades, which compositions can impart durable antibacterial and deodorizing effects to the surface of hair.
SUMMARY OF THE INVENTION
We have discovered that compounds of the formula (1) ##SPC2##
Wherein n is 0 or 1, R 1 is an aliphatic hydrocarbon radical having 8 to 14 carbon atoms, especially alkyl of 8 to 14 carbon atoms, or a tertiary butyl radical, and R 2 and R 3 each are hydrogen or alkyl having 1 to 2 carbon atoms or hydroxyalkyl having 1 to 2 carbon atoms, with the proviso that at least one of R 2 and R 3 is said alkyl or hydroxyalkyl group, have the following advantageous effects:
1. EXCELLENT BACTERIOSTATIC ACTION AGAINST Gram positive bacteria which are included in the class of saprogenous bacteria;
2. PREVENTING RANCIDITY CAUSED BY AUTOXIDATION OF SEBUM COMPONENTS SECRETED FROM THE SKIN OF HUMAN HEADS;
3. THEY ARE EFFECTIVELY DEPOSITED AND ADHERED ON THE SKIN OF HUMAN HEADS BY VARIOUS HAIR TREATMENT OPERATIONS SUCH AS WASHING, RINSING AND APPLICATION OF HAIR GROOMING AIDS.
This invention provides cosmetic compositions for hair containing a compound or mixture of compounds of the formula (1). The compositions of the invention possess dandruff alleviating and deodorizing properties.
Typical specific antioxidants of the formula (1) include, for example, 4,4'-thiobis (6-tert.-butyl-3 -methylphenol), 4,4'-thiobis (6-tert.- butyl -methylphenol) and bis (2-methyl-4-hydroxy-5-octylbenzyl)thioether.
These compounds are bifunctional antioxidants which contain in one molecule a phenol group acting as a radical chain propagation inhibitor and a sulfur atom acting as a peroxide decomposing agent. They prevent rancidity caused by autoxidation of sebum components secreted from the skin of human heads. They also exhibit bacteriostatic action against Gram positive bacteria as shown in Table 1.
Table 1 ____________________________________________________________ ______________ Bacteriostatic Action * of 4,4'-Thiobis (6-Tert.-Butyl-3-Methylphenol) Gram Positive Bacteria Gram Negative Bacteria Staphylococcus Bacillus Escherichia aureus subtilis coli ____________________________________________________________ ______________ 4,4'- thiobis (6-tert.- Concentration Concentration Concentration ____________________________________________________________ ______________ butyl-3- methyl- phenol) 500ppm 50ppm 500ppm 50ppm 500ppm 50ppm - - - - + + ____________________________________________________________ ______________ * According to the agar streak test method; " - " means the inhibition of growth of the bacteria; " + " means no inhibition of growth of bacteria
Because of the presence of the long chain alkyl group and the benzene ring, the compounds further possess an excellent adherence to hair and the skin of human heads.
The desired effects of this invention can be attained by applying and adhering compounds of the formula (1) on the skin and hair of human heads. For this purpose, the following three typical methods of application can be used:
1. A compound of the general formula (1) is incorporated in an amount of about 0.001 to about 2 percent by weight into a shampoo composition for removing dirt, fat and loose corneal cells from the skin and hair of human heads, which shampoo composition comprises as a principal effective ingredient an anionic surface active agent.
2. A compound of the general formula (1) is incorporated in an amount of about 0.001 to about 2 percent by weight into a hair rinsing composition for improving the softness, lustre and manageability of hair, which hair rinsing composition comprises as a principal effective ingredient a cationic surface active agent.
3. A compound of the general formula (1) is incorporated in an amount of about 0.001 to about 2 percent by weight into a hairgrooming aid used for applying various materials, such as emollients, perfumes, etc., to the skin and hair of human heads and adjusting hair styles, such as pomades, hair creams, hair oils or hair lotions, which hairgrooming comprises as a substrate an oily, alcoholic or aqueous substance.
Compounds of the formula (1) can be incorporated in conventional cosmetic compositions for hair including shampoos, rinses and hairgrooming aids. Rinses containing temporary colorants, such as water-soluble dyes can be used. However, the invention does not contemplate the use of the compounds of formula (1) in hair treating compositions which impart a lasting effect, such as permanent hair dyes and bleaches.
Hair shampoos that can be used include clear liquid shampoos, cream shampoos, gel shampoos and the like. Such shampoos are aqueous solutions usually containing from about 10 to about 30 weight percent of detergent. The detergent can be selected from those conventionally used for this purpose including soaps such as potassium soaps of coconut oil and other vegetable oils, fatty alcohol sulfates such as sodium dodecyl sulfate and various other anionic detergents. The shampoo compositions can contain various adjuncts such as calcium salt dispersing agents, sequestrants, solvents, thickening agents, hair and skin conditioning agents, finishing agents, foam builders, perfumes and preservatives.
Hair rinses that can be used are aqueous solutions of cationic detergents, such as alkyl (C 10 -C 18 ) dimethylbenzyl ammonium chlorides, usually employed in low concentrations of about 1 to 3 weight percent. The hair rinses can contain various hair conditioning agents, thickeners, solvents, perfumes, watersoluble dyes, etc.
The hairgrooming aids that can be used include brilliantines, pomades, hair oils, hair creams (water-in-oil, oil-inwater or dual emulsion type), alcohol-based hair lotions and two-phase hair lotions. Brilliantine is comprise mainly of mineral oil and waxes. Pomades are comprised mainly of animal and vegetable fats. Hair oil is comprised mainly of mineral oil and can contain vegetable oils. The brilliantine, pomade and hair oil compositions are anhydrous. They normally contain perfume. Hair creams are emulsions of water and oil. W/O emulsions generally contain 30 to 60 weight percent water, 30 to 50 weight percent oils, plus emulsifying agents, perfumes, etc. Dual emulsions are similar, but employ beeswax/borax or nonionic emulsifiers. O/W emulsions generally contain 60 to 90 weight percent water, 10 to 30 weight percent oil materials and the balance is various adjuncts. Alcohol-based hair lotions consist primarily of a solution of water-soluble alcohols such as ethanol or isopropyl alcohol, water and perfume oil. Two phase hair lotions consist primarily of an aqueous solution of water-soluble alcohol as one phase, mixed with an oil as the second phase.
The hair shampoos, hair rinses and hairgrooming aids, which serve as a base or carrier for the compounds of formula (1) according to this invention, can be of any suitable conventional formulation compatible with the compounds of formula (1). Suitable formulations of specific compositions will be readily apparent to workers in the cosmetic art. Since the present invention can employ the conventional shampoos, rinses and hairgrooming aids, it is believed unnecessary to describe same in greater detail herein.
The cosmetic compositions for treating hair containing one or more compounds of formula (1), according to the invention, can be applied to hair in accordance with the conventional techniques. The compound of formula (1) will remain adhered to the hair and scalp in an amount effective to alleviate dandruff and to reduce odor.
This invention will now be further described by reference to the following Examples.
EXAMPLE 1
A shampoo composition was prepared according to the following recipe:
Components percent by weight ______________________________________ Sodium trioxyethylene dodecyl ether 15 Sulfate Sodium dodecyl sulfate 2 Coconut fatty acid diethanolamide 7 Perfume 0.4 Colorant 0.2 4,4'-thiobis (6-tert.-butyl-2- 0.25 methylphenol) Water balance 100 ______________________________________
Panel tests were conducted comparing the use of the above composition according to this invention and, as a control, the same composition free of 4,4'-thiobis(6-tert.-butyl-2-methylphenol). More specifically, each of the above two compositions were applied for one month, respectively, to panels of test subjects each consisting of 10 men normally troubled with excessive dandruff. At the end of the test period, the scalps of the test subjects were examined. In the case of the composition of this invention, in 8 men no loose dandruff was observed and no crusts were present on the head skin. In the remaining 2 men no scab-like wet dandruff such as is seen in the case of an ordinary commercial shampoo was observed, and the head skin was clean. In the case of the control shampoo free of the active ingredient of this invention, the head skin of the test subjects showed dandruff after the treatment, the same as in the case of an ordinary commercial shampoo. Thus, it was shown that the composition of this invention has an excellent dandruff-alleviating effect.
EXAMPLE 2
A hair rinsing composition was prepared according to the following recipe:
Components percent by weight ______________________________________ Stearyldimethylbenzyl ammonium chloride 2 Cetanol 3 Polyoxyethylene nonylphenyl ether 1 Perfume 0.6 Propylene glycol 10 Colorant 0.03 4,4'-thiobis (6-tert.-butyl-3- 0.2 methylphenol) Water balance 100 ______________________________________
Hair treated with the above rinsing composition had a beautiful appearance, and the composition exhibited excellent dandruff-alleviating and deodorizing effects.
EXAMPLE 3
A hairgrooming aid composition was prepared according to the following recipe:
Components percent by weight ______________________________________ Fluid paraffin 16.0 Hydrous lanolin 7.0 Wax 2.0 Trioxyethylene lauryl ether 4.0 Polyoxyethylene(10)monostearate 20.0 Bis (2-methyl-4-hydroxy-5-octylbenzyl) 0.2 thioether Perfume 0.5 Water balance 100 ______________________________________
This composition exhibited excellent hair styling, deodorizing and dandruff-alleviating effects.
FIELD OF THE INVENTION
This invention relates to cosmetic compositions for hair, more specifically, shampoos, hair-rinsing agents, hair lotions, hair oils, hair creams and pomades, which compositions can impart durable antibacterial and deodorizing effects to the surface of hair.
SUMMARY OF THE INVENTION
We have discovered that compounds of the formula (1) ##SPC2##
Wherein n is 0 or 1, R 1 is an aliphatic hydrocarbon radical having 8 to 14 carbon atoms, especially alkyl of 8 to 14 carbon atoms, or a tertiary butyl radical, and R 2 and R 3 each are hydrogen or alkyl having 1 to 2 carbon atoms or hydroxyalkyl having 1 to 2 carbon atoms, with the proviso that at least one of R 2 and R 3 is said alkyl or hydroxyalkyl group, have the following advantageous effects:
1. EXCELLENT BACTERIOSTATIC ACTION AGAINST Gram positive bacteria which are included in the class of saprogenous bacteria;
2. PREVENTING RANCIDITY CAUSED BY AUTOXIDATION OF SEBUM COMPONENTS SECRETED FROM THE SKIN OF HUMAN HEADS;
3. THEY ARE EFFECTIVELY DEPOSITED AND ADHERED ON THE SKIN OF HUMAN HEADS BY VARIOUS HAIR TREATMENT OPERATIONS SUCH AS WASHING, RINSING AND APPLICATION OF HAIR GROOMING AIDS.
This invention provides cosmetic compositions for hair containing a compound or mixture of compounds of the formula (1). The compositions of the invention possess dandruff alleviating and deodorizing properties.
Typical specific antioxidants of the formula (1) include, for example, 4,4'-thiobis (6-tert.-butyl-3 -methylphenol), 4,4'-thiobis (6-tert.- butyl -methylphenol) and bis (2-methyl-4-hydroxy-5-octylbenzyl)thioether.
These compounds are bifunctional antioxidants which contain in one molecule a phenol group acting as a radical chain propagation inhibitor and a sulfur atom acting as a peroxide decomposing agent. They prevent rancidity caused by autoxidation of sebum components secreted from the skin of human heads. They also exhibit bacteriostatic action against Gram positive bacteria as shown in Table 1.
Table 1 ____________________________________________________________ ______________ Bacteriostatic Action * of 4,4'-Thiobis (6-Tert.-Butyl-3-Methylphenol) Gram Positive Bacteria Gram Negative Bacteria Staphylococcus Bacillus Escherichia aureus subtilis coli ____________________________________________________________ ______________ 4,4'- thiobis (6-tert.- Concentration Concentration Concentration ____________________________________________________________ ______________ butyl-3- methyl- phenol) 500ppm 50ppm 500ppm 50ppm 500ppm 50ppm - - - - + + ____________________________________________________________ ______________ * According to the agar streak test method; " - " means the inhibition of growth of the bacteria; " + " means no inhibition of growth of bacteria
Because of the presence of the long chain alkyl group and the benzene ring, the compounds further possess an excellent adherence to hair and the skin of human heads.
The desired effects of this invention can be attained by applying and adhering compounds of the formula (1) on the skin and hair of human heads. For this purpose, the following three typical methods of application can be used:
1. A compound of the general formula (1) is incorporated in an amount of about 0.001 to about 2 percent by weight into a shampoo composition for removing dirt, fat and loose corneal cells from the skin and hair of human heads, which shampoo composition comprises as a principal effective ingredient an anionic surface active agent.
2. A compound of the general formula (1) is incorporated in an amount of about 0.001 to about 2 percent by weight into a hair rinsing composition for improving the softness, lustre and manageability of hair, which hair rinsing composition comprises as a principal effective ingredient a cationic surface active agent.
3. A compound of the general formula (1) is incorporated in an amount of about 0.001 to about 2 percent by weight into a hairgrooming aid used for applying various materials, such as emollients, perfumes, etc., to the skin and hair of human heads and adjusting hair styles, such as pomades, hair creams, hair oils or hair lotions, which hairgrooming comprises as a substrate an oily, alcoholic or aqueous substance.
Compounds of the formula (1) can be incorporated in conventional cosmetic compositions for hair including shampoos, rinses and hairgrooming aids. Rinses containing temporary colorants, such as water-soluble dyes can be used. However, the invention does not contemplate the use of the compounds of formula (1) in hair treating compositions which impart a lasting effect, such as permanent hair dyes and bleaches.
Hair shampoos that can be used include clear liquid shampoos, cream shampoos, gel shampoos and the like. Such shampoos are aqueous solutions usually containing from about 10 to about 30 weight percent of detergent. The detergent can be selected from those conventionally used for this purpose including soaps such as potassium soaps of coconut oil and other vegetable oils, fatty alcohol sulfates such as sodium dodecyl sulfate and various other anionic detergents. The shampoo compositions can contain various adjuncts such as calcium salt dispersing agents, sequestrants, solvents, thickening agents, hair and skin conditioning agents, finishing agents, foam builders, perfumes and preservatives.
Hair rinses that can be used are aqueous solutions of cationic detergents, such as alkyl (C 10 -C 18 ) dimethylbenzyl ammonium chlorides, usually employed in low concentrations of about 1 to 3 weight percent. The hair rinses can contain various hair conditioning agents, thickeners, solvents, perfumes, watersoluble dyes, etc.
The hairgrooming aids that can be used include brilliantines, pomades, hair oils, hair creams (water-in-oil, oil-inwater or dual emulsion type), alcohol-based hair lotions and two-phase hair lotions. Brilliantine is comprise mainly of mineral oil and waxes. Pomades are comprised mainly of animal and vegetable fats. Hair oil is comprised mainly of mineral oil and can contain vegetable oils. The brilliantine, pomade and hair oil compositions are anhydrous. They normally contain perfume. Hair creams are emulsions of water and oil. W/O emulsions generally contain 30 to 60 weight percent water, 30 to 50 weight percent oils, plus emulsifying agents, perfumes, etc. Dual emulsions are similar, but employ beeswax/borax or nonionic emulsifiers. O/W emulsions generally contain 60 to 90 weight percent water, 10 to 30 weight percent oil materials and the balance is various adjuncts. Alcohol-based hair lotions consist primarily of a solution of water-soluble alcohols such as ethanol or isopropyl alcohol, water and perfume oil. Two phase hair lotions consist primarily of an aqueous solution of water-soluble alcohol as one phase, mixed with an oil as the second phase.
The hair shampoos, hair rinses and hairgrooming aids, which serve as a base or carrier for the compounds of formula (1) according to this invention, can be of any suitable conventional formulation compatible with the compounds of formula (1). Suitable formulations of specific compositions will be readily apparent to workers in the cosmetic art. Since the present invention can employ the conventional shampoos, rinses and hairgrooming aids, it is believed unnecessary to describe same in greater detail herein.
The cosmetic compositions for treating hair containing one or more compounds of formula (1), according to the invention, can be applied to hair in accordance with the conventional techniques. The compound of formula (1) will remain adhered to the hair and scalp in an amount effective to alleviate dandruff and to reduce odor.
This invention will now be further described by reference to the following Examples.
EXAMPLE 1
A shampoo composition was prepared according to the following recipe:
Components percent by weight ______________________________________ Sodium trioxyethylene dodecyl ether 15 Sulfate Sodium dodecyl sulfate 2 Coconut fatty acid diethanolamide 7 Perfume 0.4 Colorant 0.2 4,4'-thiobis (6-tert.-butyl-2- 0.25 methylphenol) Water balance 100 ______________________________________
Panel tests were conducted comparing the use of the above composition according to this invention and, as a control, the same composition free of 4,4'-thiobis(6-tert.-butyl-2-methylphenol). More specifically, each of the above two compositions were applied for one month, respectively, to panels of test subjects each consisting of 10 men normally troubled with excessive dandruff. At the end of the test period, the scalps of the test subjects were examined. In the case of the composition of this invention, in 8 men no loose dandruff was observed and no crusts were present on the head skin. In the remaining 2 men no scab-like wet dandruff such as is seen in the case of an ordinary commercial shampoo was observed, and the head skin was clean. In the case of the control shampoo free of the active ingredient of this invention, the head skin of the test subjects showed dandruff after the treatment, the same as in the case of an ordinary commercial shampoo. Thus, it was shown that the composition of this invention has an excellent dandruff-alleviating effect.
EXAMPLE 2
A hair rinsing composition was prepared according to the following recipe:
Components percent by weight ______________________________________ Stearyldimethylbenzyl ammonium chloride 2 Cetanol 3 Polyoxyethylene nonylphenyl ether 1 Perfume 0.6 Propylene glycol 10 Colorant 0.03 4,4'-thiobis (6-tert.-butyl-3- 0.2 methylphenol) Water balance 100 ______________________________________
Hair treated with the above rinsing composition had a beautiful appearance, and the composition exhibited excellent dandruff-alleviating and deodorizing effects.
EXAMPLE 3
A hairgrooming aid composition was prepared according to the following recipe:
Components percent by weight ______________________________________ Fluid paraffin 16.0 Hydrous lanolin 7.0 Wax 2.0 Trioxyethylene lauryl ether 4.0 Polyoxyethylene(10)monostearate 20.0 Bis (2-methyl-4-hydroxy-5-octylbenzyl) 0.2 thioether Perfume 0.5 Water balance 100 ______________________________________
This composition exhibited excellent hair styling, deodorizing and dandruff-alleviating effects.