Search Images Maps Play YouTube News Gmail Drive More »
Sign in
Screen reader users: click this link for accessible mode. Accessible mode has the same essential features but works better with your reader.

Patents

  1. Advanced Patent Search
Publication numberUS3903257 A
Publication typeGrant
Publication dateSep 2, 1975
Filing dateSep 24, 1973
Priority dateSep 26, 1972
Also published asDE2348222A1
Publication numberUS 3903257 A, US 3903257A, US-A-3903257, US3903257 A, US3903257A
InventorsHaruhiko Arai, Junryo Mino, Shigeo Inoue
Original AssigneeKao Corp
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Imparting deodorizing and antibacterial effects to the hair with bifunctional antioxidants
US 3903257 A
Abstract
Cosmetic compositions for hair containing a compound of the formula (1) 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.
Images(4)
Previous page
Next page
Claims  available in
Description  (OCR text may contain errors)

United States Patent [191 Arai et a1.

[451 Sept. 2, 1975 i 1 IMPARTING DEODORIZING AND ANTIBACTERIAL EFFECTS TO THE HAIR WITH BIFUNCTIONAL ANTIOXIDANTS [75] Inventors: Haruhlko Arai, Narashino; .Iunryo Mlno, Kamagaya; Shigeo lnoue, Tokyo, all of Japan [73] Assignee: Kao Soap Co., Ltd., Tokyo, Japan [22] Filed: Sept. 24, 1973 [21 Appl. No.: 400,257

[30] Foreign Application Priority Data Sept. 26. 1972 Japan 47-96448 [52] US. Cl. 424/65; 252/106; 252/107; 424/D1G. 4; 424/70; 424/337; 424/365 [51] Int. Cl. A61K 7/32; A01N 9/12; A61K 7/06 [58] Field of Search 424/DIG. 4, 337, 65, 70; 260/609 R; 252/106, 107

Primary Examt'n0rAlbert T. Meyers Aas'istant Examiner-Vera C. Clarke Attorney, Agent, or Firm-Woodhams, Blanchard and Flynn 5 7 ABSTRACT Cosmetic compositions for hair containing a compound of the formula 1 (c11 s (ca on m wherein n is 0 or 1, R is an aliphatic hydrocarbon radical having 8 to 14 carbon atoms or a tertiary butyl radical and R and R each are hydrogen or alkyl or hydroxyalkyl having 1 or 2 carbon atoms, with the proviso that at least one of R and R is said alkyl or hydroxyalky].

2 Claims, No Drawings IMPARTING DEODORIZING AND ANTIBACTERIAL EFFECTS TO THE HAIR WITH BIFUNCTIONAL ANTIOXIDANTS 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.

Table l Bactcriostatic Action of 4 4'Thiohis (6 Tcrt.But)lIMMethylphcnol) Gram Positive Bacteria Gram Negative Bacte ria Staphylococcus Bacillus Escherichia aureus suhtilis coli 4,4- thiohis (6-tert. Concentration Concen trution Concentration hutyl3- methylphenol) 5()()ppm 5(lppm 5(l0ppm Slippm SUUppm 5(lppm According to the agar streak test method; v means the inhibition ol'grouth ofthe IIHCIL'I'IAI',

means no inhibition of growth of bacteria SUMMARY OF THE INVENTION We have discovered that compounds of the formula no (cn -s- (cn i 0H (1) wherein n is O or 1, R 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 and R 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 and R 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.

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 l 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 sur face active agent.

2. A compound of the general formula l is incorpo rated 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 l is incorporated in an amount of about 0.00l 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 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 -C dimethylbenzyl ammonium chlorides, usually employed in low concentrations of about 1 to 3 weight percent. The hair rinses can contain various hair conditioning agents, thiekeners, 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 isco'rhprised 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 l 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:

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:

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 40 Polyoxyethylene( l 0 )monostearate 20.0

-Continued Components percent by weight Bis (Z-methyl-4-hydroxy-5-octylhenzyl) 0.2

thioether Perfume 0.5 Water bulunce This composition exhibited excellent hair styling, del (CH -s- (CH wherein n is zero or one, R, is octyl or tertiary butyl,

0 and R and R each is hydrogen or alkyl having one or 2 carbon atoms, provided that at least one of R and R is said alkyl.

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.

i it l i '3'

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US1932595 *Dec 19, 1931Oct 31, 1933Winthrop Chem Co IncHalogenated bis-(hydroxy-aryl)-oxides
US2695224 *Dec 26, 1951Nov 23, 1954Monsanto ChemicalsPrevention of plant growth with arylic sulfides
US3109777 *Jun 24, 1959Nov 5, 1963OrealCompositions for treatment of the hair
US3245914 *Jun 20, 1963Apr 12, 1966Dow Chemical CoGermicidal alkylhalodiphenyl oxide sulfonate compositions
US3256201 *Jul 23, 1962Jun 14, 1966Armour & CoAntiseptic detergent compositions
US3574853 *May 11, 1967Apr 13, 1971Dow Chemical CoComposition and method of reducing serum cholesterol with thiobiscresols
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US4459285 *Feb 25, 1982Jul 10, 1984Societe Anonyme Dite: L'orealCosmetic composition for the treatment of the hair and skin comprising a powder of flowers or flower tops and a cohesion agent
US4496536 *Apr 28, 1982Jan 29, 1985Henkel Kommanditgesellschaft Auf AktienSebosuppressive cosmetic preparations containing long-chained _alkanols and antioxidants
US4569839 *Feb 25, 1982Feb 11, 1986L'orealCosmetic compositions for the treatment of the hair and skin contain in the form of a powder particles resulting from the pulverization of at least one plant substance and a cohesion agent
US4596828 *Mar 28, 1985Jun 24, 1986Merck & Co., Inc.[(2-hydroxy-5-alkoxyphenyl)methylthio]phenylmethanol and derivatives thereof useful as anti-inflammatory agents
WO2016044412A1 *Sep 16, 2015Mar 24, 2016Alps South Europe S.R.O.Topical composition containing antioxidants
Classifications
U.S. Classification424/65, 510/386, 514/712, 510/492, 424/DIG.400, 510/119
International ClassificationA61K8/46, A61Q5/02, A61Q5/00, A61K8/00, A61Q15/00, A61Q5/06, A61K
Cooperative ClassificationA61K8/46, A61Q15/00, A61Q5/02, A61Q5/06, Y10S424/04, A61Q5/006
European ClassificationA61Q5/02, A61K8/46, A61Q5/06, A61Q5/00F, A61Q15/00