CA1232204A - Reducing sebum spreading - Google Patents

Reducing sebum spreading

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Publication number
CA1232204A
CA1232204A CA000436872A CA436872A CA1232204A CA 1232204 A CA1232204 A CA 1232204A CA 000436872 A CA000436872 A CA 000436872A CA 436872 A CA436872 A CA 436872A CA 1232204 A CA1232204 A CA 1232204A
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CA
Canada
Prior art keywords
composition
serum
acne
skin
spreading
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
CA000436872A
Other languages
French (fr)
Inventor
Morris S. Herstein
Walter P. Smith
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Procter and Gamble Health and Beauty Care Ltd
Original Assignee
Richardson Vicks Ltd Great Britain
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Richardson Vicks Ltd Great Britain filed Critical Richardson Vicks Ltd Great Britain
Application granted granted Critical
Publication of CA1232204A publication Critical patent/CA1232204A/en
Expired legal-status Critical Current

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  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

REDUCING SEBUM SPREADING

Abstract A method and composition for treating human skin, having applicability to oily skin and acne in order to improve the condition thereof by reducing the spreadability of sebum on the skin surface; the inven-tion involving the application to human skin so char-acterized of a composition comprising, as an active component to reduce the spreadability of sebum, an effective amount of a quaternary halide of an N,N,N-trialkylaminoalkylene gluconamide.

Description

`~2;~2~

SEDUCING SERUM SPUDDING

Background of the Invention Serum, or skin oil, is produced in the sea-Swiss glands located in the pilosebaceou~ apparatus of the skin and reaches the skin surface through the duct of the hair follicles. The presence of excessive amounts of serum on the skin surface often results in an unattractive cosmetic condition commonly known as "oily skin". Serum also plays an important role in lo the pathogenesis of acne. Setaceous gland activity is significantly increased in acne subjects and indivi-duals with the most severe acne often haze the highest serum secretion rates.
The spreading of serum on the skin surface is thus an important cosmetic parameter since its distribution on the spin surface can determine the appearance of oiliness or greasiness and can contra-byte to the severity of acne.
It is advantageous, therefore, to have available means for reducing the flow of serum over the surface of human skin, with particular regard to skin characterized by an excessive secretion or pros-once of serum on the surface and to affected skin areas of acne patients.
It has now been discovered that qua ternary halide salts of N,N,N-trialkylaminoalkylene glucon-aside may be employed to effectively so reduce the spread ability of serum.

~2~22~4 Related References _ The qLIaternary halide salts of N,N,N-tri-alkylaminoalkylene gluconamide used in this invention are described in US. Patents 3,766,267 and 3,855,290 for use as emollients in topical and cosmetic applications. Their use, however, as agents capable of effectively reducing the spreadabilbility of serum on human skin has not been recognized heretofore.
Summary of the Invention The present invention relates to a method and composition for the topical application of a qua ternary halide salt of an N,N,N-trialkylamino-alkaline gluconamide for the treatment of human skin (including the scalp) by reducing the spread ability of serum thereon. Such method provides for the physic-logically effective treatment of human skin and has beneficial applications such as, for example, in come-tics formulated for particular use on oily skin, such as, for example, pore cleansers, scalp and hair sham pros and conditioners, and the like, following applique-lion of which the skin is perceived and felt to be less oily, and in the treatment of acne wherein the reduce lion of excessive spreading of serum is particularly desirable to help prevent spreading of the acne condo-lion.
Detailed Des~riptiGn of the Invention .
The active compounds employed in this invent lion are qua ternary halide salts of N,N,N-trialkyl-z V-1210 aminoalkylene gluconamide having the formula:

~2-(cHoH)4-c-NH-~cH2)n-Nl-cH2-cH2 X- tip SHEA
wherein X is sheller or broom and n is an integer of from 2 to 4, and preferably 3, of which the qua ternary chloride salt having the following formula is most preferred:

HO--C--C--C--C--C--C-NH- ( SHEA ) 3-N---CH2-(~H20H Of - ( II ) H OH OH H OH SHEA

The preferred qua ternary chloride salt of formula (II), chemically known asoC-gluconamidopropyl dimethyl-2-hydroxyethyl ammonium chloride (CTFA name =
Quaternium 22) is commercially available as a free-flowing 60~ aqueous solution (i.e., 60% active) marketed by the Van Dye Company, Inc. under the trade-mark "Sorrowful 60".
It has now been found that the qua ternary halides of formula (I) and, most preferably, of formula (II) markedly reduce the spread ability of serum on human skin. The improvement provided by the present invention involves the use of this beneficial effect in treating spin conditions characterized either (i) by excessive secretion or presence of serum on the skin surface, e.g., oily skin, or (ii) by acne, and thereby improve the condition thereof by the topical applique-lion of appropriate compositions containing said qua ternary halides. Such topical compositions may be either cosmetic formulations for use on oily skin or therapeutically active anti-acne formulations.

The particular type of topical cosmetic come position, which may include, for example, hand, face and body lotions and creams, scalp and hair condition-east lotions, gels and shampoos, just to name a few, is not critical. Such types of compositions are readily prepared by skilled cosmetic chemical formulators.
Similarly, the particular type of anti-acne composition is not critical nor, for that matter, is the particular therapeutic anti-acne active ingredient, for example, Bunnell peroxide, sulfur, resorcinol, derivatives of retinoic acid, chlorhydroxyquinoline, hormonal and antibacterial agents, and the like. The aforementioned ~uaternary halides of formulas (I) and (II) are non-toxic to human skin, are compatible with hydrophilic adjutants and can be readily incorporated into such topical compositions.
In preparing such compositions, it is quite apparent that the product should not be formulated in ) such manner or include any vehicle or ingredient which would substantially in effectuate the activity of said halides (I) and (II) in reducing serum spread ability on the skin surface when the product is topically applied.
It is also evident that the produce should be physic-logically compatible with the skin and be cosmetically elegant.
For purposes of this invention, an effective amount of a qua ternary halide of formula (I) and, most preferably, of formula (II) is included as an active ingredient to reduce the spread ability of serum on skin in the topical compositions for use herein and, goner-ally, at least about ~05 percent by weight, based on ~23~ V-l 21 0 the weight of the total composition (i.e. "% w/w"), is wound suitable although from about 0.3 to about 6% w/w is preferred and, most preferably, from about 0.5 to about 3% w/w.
The instant invention thus provides a method of treating human skin, characterized by an excessive ) secretion of serum or by acne, to improve the condition thereon by reducing the spread ability of serum on the skin surface which comprises topically applying to human skin so characterized a composition comprising, as an active component to reduce the spread ability of serum, an effective amount of a qua ternary halide of N,N,N-trialkylaminoalkylene gluconamide of formula (I) or formula IT The invention also provides novel anti-acne compositions for topical application comprise in, as an active ingredient to reduce serum spreading, an effective amount of said halides (I) or (II).
The method of this invention, compositions for use therein and the reduction in serum spreadable-fly afforded by said qua ternary halides will be thus-treated and better understood by reference to the following examples. The procedure utilized in testing for reduction in serum spread ability is as follows.
Testing Protocol:
From 2 to 4 mg/cm2 of the material to be tested is placed on the back of the hand and spread evenly covering a circular area of about 2 inches in diameter. After application of the testing material, a period of one hour is allowed at room temperature for equilibration. After this hour, a 4 pi drop, measured ;~232~

from a micro pipette of artificial serum supplemented with 13% by weight of skyline is deposited sub Stan-tidally in the center of the treated area. The formula-lion for artificial serum is Ingredients % w/w Skyline l8.0 Corn Oil 7.0 1:1 Mix of Glycerol Dioleate:Oleic Acid 1.0 Oleic Acid 27.0 Sorrowful 140 (Decal Owlet) 43.5 Cholesterol Palpitate 1.0 Cholesterol 2.5 100.0 After a spreading period of 10 minutes, a 1 cm diameter glass cylinder is placed over the center and the serum within the confines of the cylinder is extracted. The extraction is performed by pupating
2 x 0.5 ml allocates of hexane into the glass cylinder for 30 seconds without agitation. Both hexane extracts are each pipette into a test tube and evaporated to dryness by a nitrogen gas evaporator. The residue is resolubilized with 0.2 ml hexane and 10 us of twitter-cosine is added to the sample as an internal standard.
The amount of serum within the glass cylinder is I precisely determined by gas-liquid chromatography (GLC) via determination of the amount of skyline contained in the extract. From this data, the area covered by the spreading of the artificial serum is calculated.
The greater the amount of skyline recovered from the extract, the greater toe reduction in serum spreading.

V-12~0 I 4`

Example 1 A cosmetic product, applicable to oily skin, for deeply cleaning spin pores is prepared in accordance with the following formulation. All amounts are in parts by weight unless otherwise indicated.
Table I
.. .. . _ Ingredient Composition Alcohol* 49.1 v/v Salicylic acid 0.5 10 Acetone 0.9 v/v Ceteareth-27 (surfactant) 1.0 Propylene glycol OWE
Menthol 0.05 Tartaric acid 0.25 15 Fragrance 0.05 Water, purified us ad 100.00 v/v *Equivalent to 43.2% v/v Alcohol, Absolute.

Example 2 Compositions of Sorrowful 60 admixed with the skin pore cleanser of Example 1 in the percent concern-tractions indicated in Table II are prepared and the percent reduction in serum spreading for each composition is recorded.

Table II
. . . _ . _ Composition Example 1 Reduction In Cleaner Admixed With: Serum Spreading*
a. 0.0~ w/w Sorrowful 60 (Control) negligible (base line) b. Oily " " " " 12.3 c. 0.5% " " " " 26.4 d. 1.0% " " " " 41.2 e. 1.5~ " " " " 29.4**
lo f. 2.0% " " " " 38.8 g. 2.5% " " " " 33.8**
h. 3.0~ " " " " 42.4 i. 5.0% " " " " 70.4 *Average reading of six tests.
**Percentage is atypically low due to inclusion of one non-responsive subject.

Example 3 This example illustrates the marked reduction in serum spread ability on human skin when Sorrowful 60 is added to two commercially available creams for treating acne (each containing 10% bouncily peroxide as the active anti-acne ingredient).
Table III
-Clearasil~
Acne Treatment % w/w % Reduction In Cream* Sorrowful 60 Serum Spreading A. Tinted 0 zero B. Vanishing 0 9 " 2 21 *Marketed by Richardson-Vicks Inc., Wilson, Connecticut ~232Z~?4 Example 4 The following basic shampoo formulations, (A) one without and (B) one with l% w/w Sorrowful 60, are prepared and tested for percent reduction in serum spread ability.
Table IV _ _ Reduction In Ingredients % w/w bum Spreading A. Sodium laurel ether sulfate (30%) 40.0 4%
Citric acid an hydrous 0.3 Water 59.7 B. Sodium laurel ether sulfate (30%) 40.0 60%
lo Citric acid an hydrous 0.3 Sorrowful 60 1.0 Water 58.7 _ Example 5 The following formulation for an oil-free moisturizer-cleanser containing 3% w/w Sorrowful 60 is prepared. When tested, the percent reduction in serum spreading is 46%. In contrast, the identical formulation without the Sorrowful 60 (i.e., replaced by water) measures a 35% reduction.

Table V
~L--dients % w/w Part A:
Purified Water 79.89 Carbomer ~34 lgellina agent) 0.20 Methyl paraberl ~.18 Part B:
Deionized water 2.00 lo Sodium laurel amino preappoint 2~00 Amphoteric-2 3.00 Part C:
Purified water 2.00 Sodium hydroxide pullets Part D:
Purified water 1,00 Sorrowful 60 3.00 Part E:
Myristyl acetate l.00 Cetostearyl alcohol 1.00 Myristic acid l.50 Glycerol dilaurate 1.50 Myristyl alcohol 0.25 Propel paraben Oslo Part F:
Imidazolidinyl urea 0.30 Purified water 1.00 Total 100.00 _ _ _ . . .. _ ... _ . _ Prepare Part A by dissolving the methyl pane-Ben in the water and then adding the Carbomer 934 and heating to 70C. Separately prepare Parts B and D and heat each to 75-80C. Mix Parts B and D together and combine with Part A. Prepare Part E and heat to 80C
and add to previous mixture with stirring. Prepare Part C and add to previous mixture with stirring.
Allow mixture to cool. At about 45C the emulsion goes through an inversion phase and changes color by turning white. Prepare Part F and mix into previous mixture at about 40 C. Let mixture cool to room temperature.

32~

It will be understood by those having skill in the art that the invention is not limited to the specific examples which have been offered as particular embodiments and that modifications can be made without departing from the spirit thereof.

Claims (6)

The embodiments of the invention in which an exclu-sive property or privilege is claimed are defined as follows:
1. A topical anti-acne composition comprising an anti-acne active ingredient and, as an active component to re-duce sebum spreading, an effective amount of a quaternary hal-ide of an N,N,N-trialkylaminoalkylene gluconamide having the formula:

wherein X is chloro or bromo and n is an integer of from 2 to 4.
2. The composition of claim 1 wherein n is the in-teger 3.
3. A topical anti-acne composition comprising an anti-acne active ingredient and, as an active component to re-duce sebum spreading, an effective amount of a quaternary chlo-ride of an N,N,N-trialkylaminoalkylene gluconamide having the formula:

4. The composition of claim 3 wherein the amount of said quaternary chloride in said composition is at least 0.05 percent by weight.
5. The composition of claim 3 wherein the amount of said quaternary chloride in said composition is from about 0.3 to about 6 percent by weight.
6. The composition of claim 3 wherein the amount of said quaternary chloride in said composition is from about 0.5 to about 3 percent by weight.
CA000436872A 1982-10-04 1983-09-16 Reducing sebum spreading Expired CA1232204A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US43262182A 1982-10-04 1982-10-04
US432,621 1982-10-04

Publications (1)

Publication Number Publication Date
CA1232204A true CA1232204A (en) 1988-02-02

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ID=23716910

Family Applications (1)

Application Number Title Priority Date Filing Date
CA000436872A Expired CA1232204A (en) 1982-10-04 1983-09-16 Reducing sebum spreading

Country Status (3)

Country Link
JP (1) JPS5988421A (en)
AU (1) AU567510B2 (en)
CA (1) CA1232204A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2649718A1 (en) * 1989-07-17 1991-01-18 Int Research & Dev Co Ltd FORMULATION OF CLEANSING GEL FOR THE FACE
WO1992009264A2 (en) * 1990-11-30 1992-06-11 Richardson-Vicks, Inc. Leave-on facial emulsion compositions

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4529588A (en) * 1984-02-27 1985-07-16 Richardson-Vicks Inc. Hair conditioning shampoo
EP1611883A1 (en) * 2003-03-26 2006-01-04 Menicon Co., Ltd. Composition for ophthalmic use

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2649718A1 (en) * 1989-07-17 1991-01-18 Int Research & Dev Co Ltd FORMULATION OF CLEANSING GEL FOR THE FACE
WO1992009264A2 (en) * 1990-11-30 1992-06-11 Richardson-Vicks, Inc. Leave-on facial emulsion compositions
WO1992009264A3 (en) * 1990-11-30 1992-07-09 Richardson Vicks Inc Leave-on facial emulsion compositions

Also Published As

Publication number Publication date
AU567510B2 (en) 1987-11-26
JPH0465044B2 (en) 1992-10-16
JPS5988421A (en) 1984-05-22
AU1955883A (en) 1984-04-12

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