CA2243715C - Method for reducing skin oils and grease - Google Patents
Method for reducing skin oils and grease Download PDFInfo
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- CA2243715C CA2243715C CA002243715A CA2243715A CA2243715C CA 2243715 C CA2243715 C CA 2243715C CA 002243715 A CA002243715 A CA 002243715A CA 2243715 A CA2243715 A CA 2243715A CA 2243715 C CA2243715 C CA 2243715C
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- skin
- esters
- alkyl
- grease
- salicylate
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/008—Preparations for oily skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/08—Antiseborrheics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/008—Preparations for oily hair
Abstract
A cosmetic method is provided for reducing or inhibiting oil and grease generation from human skin by applying to the skin a C11-C30 alkyl or alkenyl ester of salicylic acid as an active component in combination with a pharmaceutically acceptable carrier. Most preferred is tridecyl salicylate.
Description
turFmHOD FOR REDUCING SKIN OILS AND GREASE
Rp,c~KGROUND OF THE INVENTION
F~ Ald of the Invent~.on The invention relates to a method for controlling oil and grease secretion from skin.
mt,e Related Art Sebum is produced by the disruption of the cells in which it is formed (in the basal layer of the gland). This function may be termed holocrine secretion.
Being liquid inside the duct and hair follicle, sebum diffuses up and down the follicular canal. Upon reaching the skin surface it combines with epithelial lipids (from the keratinizing cells) and emulsifies as an oily liquid with water from the sweat glands. In this way a semi-solid, slightly acid, hydrophilic film is formed on the skin and in the hair follicles. The quantity of sebum produced is directly proportional to the size of the gland.
The rate of sebum production varies in different individuals, some having oilier skins than others. Male sex hormones increase sebum production. Increased temperature also increases production.
The literature is replete with methods and compositions for eliminating, treating or at least reducing the levels of skin oils and greasiness. None have proved totally satisfactory.
Rp,c~KGROUND OF THE INVENTION
F~ Ald of the Invent~.on The invention relates to a method for controlling oil and grease secretion from skin.
mt,e Related Art Sebum is produced by the disruption of the cells in which it is formed (in the basal layer of the gland). This function may be termed holocrine secretion.
Being liquid inside the duct and hair follicle, sebum diffuses up and down the follicular canal. Upon reaching the skin surface it combines with epithelial lipids (from the keratinizing cells) and emulsifies as an oily liquid with water from the sweat glands. In this way a semi-solid, slightly acid, hydrophilic film is formed on the skin and in the hair follicles. The quantity of sebum produced is directly proportional to the size of the gland.
The rate of sebum production varies in different individuals, some having oilier skins than others. Male sex hormones increase sebum production. Increased temperature also increases production.
The literature is replete with methods and compositions for eliminating, treating or at least reducing the levels of skin oils and greasiness. None have proved totally satisfactory.
Accordingly, it is an object of the present invention to provide an improved method for controlling, reducing or inhibiting oiliness and greasiness in human skin. This and other objects of the present invention will become more fully apparent from the subsequent summary and detailed ~ ' discussion.
yr,UMMARY OF THE INVENTION
A cosmetic method for reducing or inhibiting oiliness and greasiness in human skin is provided which involves topical application to the skin of a safe and effective amount of salicylate ester in a pharmaceutically acceptable carrier, the salicylate ester having the formula (I):
COOK
OH
/
wherein R is a C,1-C3o alkyl or alkenyl radical.
25.. The invention further provides the use of salicylate ester having the formula (I) above in reducing or inhibiting oiliness and greasiness in human skin.
The invention also comprises the use of a cosmetic composition comprising salicylate ester having formula I
above, in a pharmaceutically acceptable carrier, in reducing or inhibiting oiliness and greasiness in human skin.
f WO 98!23257 PCT/EP97/06693 -DETAILED DESCRIPTION OF THE INVENTTON
Now it has been discovered that oil and grease production by skin may be controlled, reduced and/or inhibited through application of a cosmetic composition including as active a derivative of salicylic acid having formula (I):
COOK
OH
wherein_R_ is a C11-C3o alkyl or alkenyl radical. Most preferred are the C12-CZO alkyl or alkenyl, optimally the. C13 alkyl or alkenyl esters of salicylic acid. By the term "skin" is meant to include all areas containing sebaceous glands, such as face, back, chest and scalp.
"Safe arid effective amounts" of the C1,-C3o esters of salicylic acid are to be used within cosmetic compositions of the present invention. The term "safe and effective amounts" are defined as any amount sufficient to significantly induce a positive modification in lipid production but low enough to avoid any undesirable side effects (at a reasonable benefit/risk ratio), within the scope of sound medical judgement. The safe and effective amount of the salicylate esters will vary with the particular age and physical condition of the subject being evaluated, the severity of the condition, the duration of the treatment, the nature of concurrent therapy, the specific ester employed, the particular pharmaceutically-acceptable carrier utilized, and like factors. Generally these amounts may range from 0.01 to 20%, preferably from 0.1 to 10%, more preferably from 1 to 8%, optimally from 2 to 6% by weight of the composition.
Besides the active salicylate ester, compositions of the present invention will utilize a pharmaceutically, physiologically and/or cosmetically acceptable carrier. The carrier may either be aqueous, anhydrous or an emulsion.
10_ Preferably the compositions are aqueous, especially water and oil emulsions of the W/O or O/W variety. Water when present will be in amounts which may range from 5 to 95%, preferably from 20 to 70%, optimally between 35 and 60% by weight.
Besides water, relatively volatile solvents may also serve as carriers within compositions of the present invention. Most preferred are monohydric C1-C3 alkanols.
These include ethyl alcohol, methyl alcohol and isopropyl alcohol. The amount of monohydric alkanol may range from 1 to 70%, preferably from 10 to 50%, optimally between I5 to 40% by weight.
Emollient materials may also serve as pharmaceutically physiologically and/or cosmetically acceptable carriers.
These may be in the form of silicone oils and synthetic esters. Amounts of the emollients may range anywhere from 0.1 to 50%, preferably between 1 and 20% by weight.
Silicone oils may be divided into the volatile and non-volatile variety. The term "volatile" as used herein , refers to those materials which have a measurable vapor pressure at ambient temperature. Volatile silicone oils are preferably chosen from cyclic or linear polydimethyl-siloxanes containing from 3 to 9, preferably from 4 to 5, silicon atoms.
Linear volatile silicone materials generally have viscosities less than 5 centistokes at 25°C while cyclic materials typically have viscosities of less than 10 centistokes.
Nonvolatile silicone oils useful as an emollient material include polyalkyl siloxanes, polyalkylaryl siloxanes and polyether siloxane copolymers. The essentially non-volatile polyalkyl siloxanes useful herein include, for example, polydimethyl siloxanes with viscosities of from 5 to 100,000 centistokes at 25°C. Among the preferred non-volatile emollients useful in the present compositions are the polydimethyl siloxanes having viscosities from 10 to 400 centistokes at 25°C.
Among the ester emollients are:
(1) Alkenyl or alkyl esters of fatty acids having 10 to 20 carbon atoms. Examples thereof include isoarachidyl neopentanoate, isononyl isonanonoate, oleyl myristate, oleyl stearate, and oleyl oleate.
(2) Ether-esters such as fatty acid esters of ethoxylated fatty alcohols.
(3) Polyhydric alcohol esters. Ethylene glycol mono and di-fatty acid esters, diethylene glycol mono-and di-fatty acid esters, polyethylene glycol (200-6000) mono- and di-fatty acid esters, propylene glycol mono- and di-fatty acid esters, polypropylene glycol 2000 monooleate, a polypropylene glycol 2000 monostearate, ethoxylated propylene glycol monostearate, glyceryl mono- and di-fatty acid esters, polyglycerol poly-fatty esters, ethoxylated glyceryl monostearate, 1,3-butylene glycol monostearate, 1,3-butylerie glycol distearate, polyoxyethylene polyol fatty acid ester, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters are satisfactory polyhydric alcohol esters.
(4) Wax esters such as beeswax, spermaceti, myristyl myristate, stearyl stearate and arachidyl behenate.
(5) Sterols esters, of which cholesterol fatty acid esters are examples thereof.
Fatty acids having from 10 to 30 carbon atoms may also 15_ be included as pharmaceutically acceptable carriers for compositions of this invention. Illustrative of this category are pelarganic, lauric, myristic, palmitic, stearic, isostearic, hydroxystearic, oleic, linoleic, ricinoleic, arachidic, behenic and erucic acids.
Humectants of the polyhydric alcohol-type may also be employed as pharmaceutically acceptable carriers in compositions of this invention. The humectant aids in increasing the effectiveness of the emollient, reduces scaling, stimulates removal of built-up scale and improves skin feel. Typical polyhydric alcohols include glycerol, polyalkylene glycols and more preferably alkylene polyols and their derivatives, including propylene glycol, dipropylene glycol, polypropylene glycol, polyethylene glycol and derivatives thereof, sorbitol, hydroxypropyl sorbitol, hexylene glycol, 1,3-butylene glycol, , 1,2,6-hexanetriol, ethoxylated glycerol, propoxylated glycerol and mixtures thereof. For best results the humectant is preferably propylene glycol. The amount of humectant may range anywhere from 0.5 to 30~, preferably between 1 and 15~ by weight of the composition.
Thickeners may also be utilized as part of the pharmaceutically acceptable carrier of compositions according to the present invention. Typical thickeners include crosslinked acrylates (e. g. Carbopol 982~), hydrophobically-modified acrylates (e.g. Carbopol 1382~), cellulosic derivatives and natural gums. Among useful cellulosic derivatives are sodium carboxymethylcellulose, hydroxypropyl methylcellulose, hydroxypropyl cellulose, hydroxyethyl cellulose, ethyl cellulose and hydroxymethyl cellulose. Natural gums suitable for the present invention include guar, xanthan, sclerotium, carrageenan, pectin and combinations of these gums. Amounts of the thickener may range from 0.0001 to 5~, usually from 0.001 to 10, optimally from 0.01 to 0.5~ by weight. .
Collectively the water, solvents, silicones, esters, fatty acids, humectants and/or thickeners will constitute the pharmaceutically acceptable carrier in amounts from 1 to 99.9, preferably from 80 to 99o by weight.
Cosmetic compositions of the present invention may be in any form. These forms may include emulsified systems such as lotions and creams, microemulsions, roll-on formulations, mousses, ointments (hydrophilic and hydrophobic), aerosol and non-aerosol sprays and pad-applied formulations. ,-...
Surfactants may also be present in cosmetic compositions of the present invention. Total concentration of the surfactant will range from 0.1 to 40~, preferably from 1 to 20~, optimally from 1 to 5~ by weight of the composition. The surfactant may be selected from the group WO 98/23257 - PCT/EP971~6693 -_ g -consisting of anionic, nonionic, cationic and amphoteric actives. Particularly preferred nonionic surfactants are those with a Clo-CZO fatty alcohol or acid hydrophobe ' condensed with from 2 to 100 moles of ethylene oxide or propylene oxide per mole of hydrophabe; C2-Clo alkyl phenols condensed with from 2 to 20 moles of alkylene oxide; mono-and di- fatty acid esters of ethylene glycol; fatty acid monoglyceride; sorbitan,.mono- and di- CB-Czo fatty acids;
block copolymers (ethylene oxidetpropylene oxidea; and polyoxyethylene sorbitan as well as combinations thereof.
Alkyl polyglycosides and saccharide fatty amides (e. g.
methyl gluconamides? are also suitable nonionic surfactants.
25 Preferred anionic surfactants include soap, alkyl ether sulfate and sulfonates, alkyl sulfates and sulfonates, aikylbenzene sulfonates, alkyl and dialkyl sulfosuccinates, C$-Czo acyl isethionates, acyl glutamates, Ce-C2o alkyl ether phosphates and combinations thereof.
Sunscreen actives may also be included in compositions of the present invention. Particularly preferred are such materials as ethylhexyl p-methoxycinnamate, available as Parsol MCX, and benzophenone-3, also known as Oxybenzone.
Inorganic sunscreen actives may be employed such as microfine titanium dioxide, polyethylene and various other polymers. Amounts of the sunscreen agents will generally range from 0.1 to 30~, preferably from 2 to 20~, optimally from 4 to 10~ by weight.
Preservatives can desirably be incorporated into the cosmetic compositions of this invention to protect against the growth of potentially harmful microorganisms. Suitable traditional preservatives for compositions of this invention are alkyl esters of para-hydroxybenzoic acid.
WO 98123257 - PC'T/EP97I06693 -Other preservatives which have more recently come into use include hydantoin derivatives, propionate salts, and a variety_of quaternary ammonium compounds. Cosmetic chemists are familiar with appropriate preservatives and ' 5 routinely choose them to satisfy the preservative challenge test and to provide product stability. Particularly preferred preservatives are phenoxyethanol, methyl paraben, propyl paraben, imidazolidinyl urea, sodium dehydroacetate and benzyl alcohol. The preservatives should be selected having regard for the use of the composition and possible incompatibilities between the preservatives and other ingredients in the emulsion. Preservatives are preferably employed in amounts ranging from 0.01 to 2~ by weight of the composition.
Compositions of the present invention may also contain water-soluble vitamins. The term water-soluble defines substances with a solubility of at least 0.1~, preferably at least 1~, optimally at least 5~ by weight in water.
Illustrative water-soluble vitamins are Niacin, Vitamin B6, Vitamin C and Biotin. One source for Vitamin C is a product sold under the trademark of Vitazyme C available from the Brooks Company. Niacin, Vitamin B and Biotin are available from Roche Pharmaceuticals. Total amount of vitamins in compositions according to the present invention may range from 0.001 to 1~, preferably from 0.01 to 0.6, optimally from 0.1 to 0.5~ by weight.
Keratolytic agents such as CZ-C25 oc-hydroxy alkanoic acids may also be incorporated into compositions of this invention. Illustrative of this group of materials are glycolic, lactic, oc-hydroxyoctanoic acids and salts thereof. The salts may be selected from alkalimetal, ammonium and C1-Czo alkyl or_alkanolammonium counterions.
- 10 ~--Levels of oc-hydroxyalkanoic acids may range from 0.001 to 10~, preferably between 0.2 and 1~, optimally between 0.4 and 0.5~ by weight.
Minor adjunct ingredients may also be present in the cosmetic compositions. Among them may be the water-insoluble vitamins such as Vitamin A Palmitate, Vitamin E
Acetate and DL-panthenol.
Another adjunct ingredient can be that of an enzyme.
Particularly preferred is superoxide dismutase, commercially available as Biocell SOD from Brooks Industries, USA.
15- Natural vegetable materials from renewable resources are often desirable in cosmetic compositions. For instance, cosmetic compositions of the present invention may include ~-glucan derived from oats, commercially available under the trademark Microat SF from Nurture Inc., Missoula, Montana.
Colorants, fragrances, opacifiers and abrasives may also be included in compositions of the present invention.
Each of these substances may range from 0.05 to 5~, - preferably between 0.1 and 3~ by weight.
The following Examples will more fully illustrate embodiments of this invention.
All parts, percentages and proportions referred to herein and in the appended claims are by weight of the composition ' unless otherwise indicated.
a WO 98/23257 PCTlEP97/06693 -- 11 - ' The following skin oil and grease reducing sunscreen creme is prepared having a composition described in Table I.
TABLE I
COMPONENT WETGHT '36 Carbopol 1382~ (2~ solids) 8.000 Spectron SA-13~ (Tridecyl Salicylate) 6.000 Parsol MCX~ 6.000 Isoarachidyl Neopentanoate 4.300 Benzophenone-3 3.000 -Glycerin 3.000 Isononyl Isononanoate 2.500 Arlacel 165 VS~ (GMS/PEG) 1.700 BRIJ 721 (Vegetable) 1.200 Isostearic Acid 1.200 Polymethyl Methacrylate 1.000 Cetyl Alcohol 1.000 Triethanolamine 0.770 Phenoxyethanol 0.700 Actiglyde-J Special~ (Bio-hyaluronic 0.500 acid) Vitamin E Acetate 0.500 BRIJ 72~ (Vegetable) 0.300 Methylparaben 0.300 Polyethylene (A-C 400)~ 0.300 Algae Extract 0.250 Glydant~ 0.200 DL-Panthenol 0.200 C1,-C,a Acid-PEG 8 Esters 0.200 Trilaureth-4-Phosphate 0.200 Silicone 200 (l0cst) 0.200 Microat SF~ 0.200 Niacin 0.200 Amigel~ 0.170 Vitazyme C~ 0.100 Superoxide Dismutase 0.100 ..
Vitamin B6 0.100 Vitamin A Palmitate 0.100 Propylparaben 0.100 Disodium EDTA 0.100 L-Lactic Acid 0.010 Biotin 0.001 Deionized water qs Another skin oil and grease inhibiting creme is prepared having a composition described in Table II.
TABLE II
COMPONENT WEIGFIT
'~s Carbopol 1382~ (2~ Solids) 18.000 Cyclomethicone _ 6.000 Cetyl Alcohol 4.400 Spectron SA-13~ (Tridecyl Salicylate)4.000 Glycerin 3.000 Isoarachidyl Neopentanoate 2.400 Emulgade 1000 NI~ 1.750 willowbark Extract 1.500 Triethanolamine 99~ 1.420 C18-C36 Fatty Acid 1 .200 BRIJ 721m (Vegetable) 1.200 Arachidyl Behenate 1.000 Actiglyde-J Special~ 1.000 Polymethyl Methacrylate 1.000 Vitamin E Acetate - 1.000 Sodium Pyrolidone Carboxylate (50~ 0.750 solids) Algae Extract 0.500 DL-Panthenol 0.500 Silicone 200 (10 cst) 0.400 C1z-C=o Acid-PEG 8 Esters 0.400 Microat SF~ 0.360 Bernel Ester TOC~ 0.360 Glydant~ 0.300 Methylparaben 0.300 BRIJ 72c~ (Vegetable) 0.300 Polyethylene (A-C 400)~ 0.300 Shea Butter 0.200 Disodium EDTA 0.100 Amigel~ 0.100 Propylparaben 0.100 Vitamin A Palmitate 0.100 L-Lactic Acid 0.010 Biotin 0.001 Vitazyme C~ 0_001 Deionized Water qs WO 98!23257 - PCT/EP97I06693 -The present Example reports an in vitro analysis of sebum suppression by use of a salicylate ester.
3<n yitro Sebocvte Linoaenesis Assay Human sebaceous glands were isolated from the nose of a male (age 60) and cultured using submerged tissue culture techniques (Bajor et al, J. Invest. Dermatol. 102:1994. P.
564). These sebocytes accumulate intracellular lipid droplets characteristic of mature human sebum.
Harvested and passaged sebocytes were added to each well of a 48 well tissue culture plate and incubated at 37°C in the presence of 7.5~ COz for 10 days. The growth medium was changed three times per week. On the day of experimentation, the growth medium was removed and the sebocytes washed three times with phosphate buffered saline (PBS). Fresh PBS in 0.5 ml amount was added to each well and 10 microliters of active agent speculated to inhibit lipogenesis_ Triplicate wells were utilized for each sample. Controls consisted of PBS, dimethyl sulfoxide (DMSO) used to solubilize the lipophilic compounds, and phenol red, a compound which possesses estrogen-like activity. The cultures were incubated at 37°C/7.5~ COZ for minutes. Radioactive label was prepared by adding 30 100 ~t.l of 14-C labelled acetic acid (Amersham, sodium salt, specific activity of 56 mCi/mmol) to 10 ml of 50 mM sodium acetate buffer. Then 50 ~t.l was added to each well containing the sebocytes and active agents. The cultures were returned to the incubator for 4 hours. Thereafter the treatments and label were removed and the sebocytes rinsed WO 98!23257 PCT/EP97/06693 -three times with fresh PBS. Sebocytes were harvested and microliters removed and set aside for protein -assessment. The remaining samples containing the 14-C
label were extracted and the label counted using a Beckman 5 scintillation counter. Triplicates were performed for each sample.
For each 48 well tissue culture plate, 16 samples could be analyzed. Of these, 1 sample was reserved for 10 PBS, 1 sample for DMSO, and 1 sample for phenol red leaving 13 remaining samples.
TABLE I
Tridecv~.s~licvlate 9s Reduction standard Devi~.t3.on Concentration 0.00003 8.5 2.5 0.0003 13.3 1.0 0.003 28.3 2.1 0.01 44.7 9.7 0.03 49.1 6.3 0.05 48.9 8_5 0.1~ 63.0 7.7 WO 98/23257 PCTlEP97/06693 -TABLE II
Octvlsalicvlate ~ Reduction Standard Deviation Conc.
0.005 11.6 12.2 0.01 11.6 4.1 0.05 22.4 15.1 0.1~ 8.3 19.7 0.5~ 0 12.6 1.0~ 2.2 7.8 0.1~ Phenol Red 40.8 12.5 Salicylic Acid conc ~ Reduction Standard Deviation 0.00014 11.4 9.0 0.0014 10.1 10.5 0.014% 13.1 13.4 0.14 3.6 ~.4 Based on the results In Tables I, II and III, it is evident that tridecyl salicylate has significant activity in reducing oiliness and grease, especially compared to octylsalicylate and salicylic acid.
The foregoing description and examples illustrate selected embodiments of the present invention. Tn light thereof, various modifications will be suggested to one skilled in the art, all of which are within the spirit and purview of this invention.
yr,UMMARY OF THE INVENTION
A cosmetic method for reducing or inhibiting oiliness and greasiness in human skin is provided which involves topical application to the skin of a safe and effective amount of salicylate ester in a pharmaceutically acceptable carrier, the salicylate ester having the formula (I):
COOK
OH
/
wherein R is a C,1-C3o alkyl or alkenyl radical.
25.. The invention further provides the use of salicylate ester having the formula (I) above in reducing or inhibiting oiliness and greasiness in human skin.
The invention also comprises the use of a cosmetic composition comprising salicylate ester having formula I
above, in a pharmaceutically acceptable carrier, in reducing or inhibiting oiliness and greasiness in human skin.
f WO 98!23257 PCT/EP97/06693 -DETAILED DESCRIPTION OF THE INVENTTON
Now it has been discovered that oil and grease production by skin may be controlled, reduced and/or inhibited through application of a cosmetic composition including as active a derivative of salicylic acid having formula (I):
COOK
OH
wherein_R_ is a C11-C3o alkyl or alkenyl radical. Most preferred are the C12-CZO alkyl or alkenyl, optimally the. C13 alkyl or alkenyl esters of salicylic acid. By the term "skin" is meant to include all areas containing sebaceous glands, such as face, back, chest and scalp.
"Safe arid effective amounts" of the C1,-C3o esters of salicylic acid are to be used within cosmetic compositions of the present invention. The term "safe and effective amounts" are defined as any amount sufficient to significantly induce a positive modification in lipid production but low enough to avoid any undesirable side effects (at a reasonable benefit/risk ratio), within the scope of sound medical judgement. The safe and effective amount of the salicylate esters will vary with the particular age and physical condition of the subject being evaluated, the severity of the condition, the duration of the treatment, the nature of concurrent therapy, the specific ester employed, the particular pharmaceutically-acceptable carrier utilized, and like factors. Generally these amounts may range from 0.01 to 20%, preferably from 0.1 to 10%, more preferably from 1 to 8%, optimally from 2 to 6% by weight of the composition.
Besides the active salicylate ester, compositions of the present invention will utilize a pharmaceutically, physiologically and/or cosmetically acceptable carrier. The carrier may either be aqueous, anhydrous or an emulsion.
10_ Preferably the compositions are aqueous, especially water and oil emulsions of the W/O or O/W variety. Water when present will be in amounts which may range from 5 to 95%, preferably from 20 to 70%, optimally between 35 and 60% by weight.
Besides water, relatively volatile solvents may also serve as carriers within compositions of the present invention. Most preferred are monohydric C1-C3 alkanols.
These include ethyl alcohol, methyl alcohol and isopropyl alcohol. The amount of monohydric alkanol may range from 1 to 70%, preferably from 10 to 50%, optimally between I5 to 40% by weight.
Emollient materials may also serve as pharmaceutically physiologically and/or cosmetically acceptable carriers.
These may be in the form of silicone oils and synthetic esters. Amounts of the emollients may range anywhere from 0.1 to 50%, preferably between 1 and 20% by weight.
Silicone oils may be divided into the volatile and non-volatile variety. The term "volatile" as used herein , refers to those materials which have a measurable vapor pressure at ambient temperature. Volatile silicone oils are preferably chosen from cyclic or linear polydimethyl-siloxanes containing from 3 to 9, preferably from 4 to 5, silicon atoms.
Linear volatile silicone materials generally have viscosities less than 5 centistokes at 25°C while cyclic materials typically have viscosities of less than 10 centistokes.
Nonvolatile silicone oils useful as an emollient material include polyalkyl siloxanes, polyalkylaryl siloxanes and polyether siloxane copolymers. The essentially non-volatile polyalkyl siloxanes useful herein include, for example, polydimethyl siloxanes with viscosities of from 5 to 100,000 centistokes at 25°C. Among the preferred non-volatile emollients useful in the present compositions are the polydimethyl siloxanes having viscosities from 10 to 400 centistokes at 25°C.
Among the ester emollients are:
(1) Alkenyl or alkyl esters of fatty acids having 10 to 20 carbon atoms. Examples thereof include isoarachidyl neopentanoate, isononyl isonanonoate, oleyl myristate, oleyl stearate, and oleyl oleate.
(2) Ether-esters such as fatty acid esters of ethoxylated fatty alcohols.
(3) Polyhydric alcohol esters. Ethylene glycol mono and di-fatty acid esters, diethylene glycol mono-and di-fatty acid esters, polyethylene glycol (200-6000) mono- and di-fatty acid esters, propylene glycol mono- and di-fatty acid esters, polypropylene glycol 2000 monooleate, a polypropylene glycol 2000 monostearate, ethoxylated propylene glycol monostearate, glyceryl mono- and di-fatty acid esters, polyglycerol poly-fatty esters, ethoxylated glyceryl monostearate, 1,3-butylene glycol monostearate, 1,3-butylerie glycol distearate, polyoxyethylene polyol fatty acid ester, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters are satisfactory polyhydric alcohol esters.
(4) Wax esters such as beeswax, spermaceti, myristyl myristate, stearyl stearate and arachidyl behenate.
(5) Sterols esters, of which cholesterol fatty acid esters are examples thereof.
Fatty acids having from 10 to 30 carbon atoms may also 15_ be included as pharmaceutically acceptable carriers for compositions of this invention. Illustrative of this category are pelarganic, lauric, myristic, palmitic, stearic, isostearic, hydroxystearic, oleic, linoleic, ricinoleic, arachidic, behenic and erucic acids.
Humectants of the polyhydric alcohol-type may also be employed as pharmaceutically acceptable carriers in compositions of this invention. The humectant aids in increasing the effectiveness of the emollient, reduces scaling, stimulates removal of built-up scale and improves skin feel. Typical polyhydric alcohols include glycerol, polyalkylene glycols and more preferably alkylene polyols and their derivatives, including propylene glycol, dipropylene glycol, polypropylene glycol, polyethylene glycol and derivatives thereof, sorbitol, hydroxypropyl sorbitol, hexylene glycol, 1,3-butylene glycol, , 1,2,6-hexanetriol, ethoxylated glycerol, propoxylated glycerol and mixtures thereof. For best results the humectant is preferably propylene glycol. The amount of humectant may range anywhere from 0.5 to 30~, preferably between 1 and 15~ by weight of the composition.
Thickeners may also be utilized as part of the pharmaceutically acceptable carrier of compositions according to the present invention. Typical thickeners include crosslinked acrylates (e. g. Carbopol 982~), hydrophobically-modified acrylates (e.g. Carbopol 1382~), cellulosic derivatives and natural gums. Among useful cellulosic derivatives are sodium carboxymethylcellulose, hydroxypropyl methylcellulose, hydroxypropyl cellulose, hydroxyethyl cellulose, ethyl cellulose and hydroxymethyl cellulose. Natural gums suitable for the present invention include guar, xanthan, sclerotium, carrageenan, pectin and combinations of these gums. Amounts of the thickener may range from 0.0001 to 5~, usually from 0.001 to 10, optimally from 0.01 to 0.5~ by weight. .
Collectively the water, solvents, silicones, esters, fatty acids, humectants and/or thickeners will constitute the pharmaceutically acceptable carrier in amounts from 1 to 99.9, preferably from 80 to 99o by weight.
Cosmetic compositions of the present invention may be in any form. These forms may include emulsified systems such as lotions and creams, microemulsions, roll-on formulations, mousses, ointments (hydrophilic and hydrophobic), aerosol and non-aerosol sprays and pad-applied formulations. ,-...
Surfactants may also be present in cosmetic compositions of the present invention. Total concentration of the surfactant will range from 0.1 to 40~, preferably from 1 to 20~, optimally from 1 to 5~ by weight of the composition. The surfactant may be selected from the group WO 98/23257 - PCT/EP971~6693 -_ g -consisting of anionic, nonionic, cationic and amphoteric actives. Particularly preferred nonionic surfactants are those with a Clo-CZO fatty alcohol or acid hydrophobe ' condensed with from 2 to 100 moles of ethylene oxide or propylene oxide per mole of hydrophabe; C2-Clo alkyl phenols condensed with from 2 to 20 moles of alkylene oxide; mono-and di- fatty acid esters of ethylene glycol; fatty acid monoglyceride; sorbitan,.mono- and di- CB-Czo fatty acids;
block copolymers (ethylene oxidetpropylene oxidea; and polyoxyethylene sorbitan as well as combinations thereof.
Alkyl polyglycosides and saccharide fatty amides (e. g.
methyl gluconamides? are also suitable nonionic surfactants.
25 Preferred anionic surfactants include soap, alkyl ether sulfate and sulfonates, alkyl sulfates and sulfonates, aikylbenzene sulfonates, alkyl and dialkyl sulfosuccinates, C$-Czo acyl isethionates, acyl glutamates, Ce-C2o alkyl ether phosphates and combinations thereof.
Sunscreen actives may also be included in compositions of the present invention. Particularly preferred are such materials as ethylhexyl p-methoxycinnamate, available as Parsol MCX, and benzophenone-3, also known as Oxybenzone.
Inorganic sunscreen actives may be employed such as microfine titanium dioxide, polyethylene and various other polymers. Amounts of the sunscreen agents will generally range from 0.1 to 30~, preferably from 2 to 20~, optimally from 4 to 10~ by weight.
Preservatives can desirably be incorporated into the cosmetic compositions of this invention to protect against the growth of potentially harmful microorganisms. Suitable traditional preservatives for compositions of this invention are alkyl esters of para-hydroxybenzoic acid.
WO 98123257 - PC'T/EP97I06693 -Other preservatives which have more recently come into use include hydantoin derivatives, propionate salts, and a variety_of quaternary ammonium compounds. Cosmetic chemists are familiar with appropriate preservatives and ' 5 routinely choose them to satisfy the preservative challenge test and to provide product stability. Particularly preferred preservatives are phenoxyethanol, methyl paraben, propyl paraben, imidazolidinyl urea, sodium dehydroacetate and benzyl alcohol. The preservatives should be selected having regard for the use of the composition and possible incompatibilities between the preservatives and other ingredients in the emulsion. Preservatives are preferably employed in amounts ranging from 0.01 to 2~ by weight of the composition.
Compositions of the present invention may also contain water-soluble vitamins. The term water-soluble defines substances with a solubility of at least 0.1~, preferably at least 1~, optimally at least 5~ by weight in water.
Illustrative water-soluble vitamins are Niacin, Vitamin B6, Vitamin C and Biotin. One source for Vitamin C is a product sold under the trademark of Vitazyme C available from the Brooks Company. Niacin, Vitamin B and Biotin are available from Roche Pharmaceuticals. Total amount of vitamins in compositions according to the present invention may range from 0.001 to 1~, preferably from 0.01 to 0.6, optimally from 0.1 to 0.5~ by weight.
Keratolytic agents such as CZ-C25 oc-hydroxy alkanoic acids may also be incorporated into compositions of this invention. Illustrative of this group of materials are glycolic, lactic, oc-hydroxyoctanoic acids and salts thereof. The salts may be selected from alkalimetal, ammonium and C1-Czo alkyl or_alkanolammonium counterions.
- 10 ~--Levels of oc-hydroxyalkanoic acids may range from 0.001 to 10~, preferably between 0.2 and 1~, optimally between 0.4 and 0.5~ by weight.
Minor adjunct ingredients may also be present in the cosmetic compositions. Among them may be the water-insoluble vitamins such as Vitamin A Palmitate, Vitamin E
Acetate and DL-panthenol.
Another adjunct ingredient can be that of an enzyme.
Particularly preferred is superoxide dismutase, commercially available as Biocell SOD from Brooks Industries, USA.
15- Natural vegetable materials from renewable resources are often desirable in cosmetic compositions. For instance, cosmetic compositions of the present invention may include ~-glucan derived from oats, commercially available under the trademark Microat SF from Nurture Inc., Missoula, Montana.
Colorants, fragrances, opacifiers and abrasives may also be included in compositions of the present invention.
Each of these substances may range from 0.05 to 5~, - preferably between 0.1 and 3~ by weight.
The following Examples will more fully illustrate embodiments of this invention.
All parts, percentages and proportions referred to herein and in the appended claims are by weight of the composition ' unless otherwise indicated.
a WO 98/23257 PCTlEP97/06693 -- 11 - ' The following skin oil and grease reducing sunscreen creme is prepared having a composition described in Table I.
TABLE I
COMPONENT WETGHT '36 Carbopol 1382~ (2~ solids) 8.000 Spectron SA-13~ (Tridecyl Salicylate) 6.000 Parsol MCX~ 6.000 Isoarachidyl Neopentanoate 4.300 Benzophenone-3 3.000 -Glycerin 3.000 Isononyl Isononanoate 2.500 Arlacel 165 VS~ (GMS/PEG) 1.700 BRIJ 721 (Vegetable) 1.200 Isostearic Acid 1.200 Polymethyl Methacrylate 1.000 Cetyl Alcohol 1.000 Triethanolamine 0.770 Phenoxyethanol 0.700 Actiglyde-J Special~ (Bio-hyaluronic 0.500 acid) Vitamin E Acetate 0.500 BRIJ 72~ (Vegetable) 0.300 Methylparaben 0.300 Polyethylene (A-C 400)~ 0.300 Algae Extract 0.250 Glydant~ 0.200 DL-Panthenol 0.200 C1,-C,a Acid-PEG 8 Esters 0.200 Trilaureth-4-Phosphate 0.200 Silicone 200 (l0cst) 0.200 Microat SF~ 0.200 Niacin 0.200 Amigel~ 0.170 Vitazyme C~ 0.100 Superoxide Dismutase 0.100 ..
Vitamin B6 0.100 Vitamin A Palmitate 0.100 Propylparaben 0.100 Disodium EDTA 0.100 L-Lactic Acid 0.010 Biotin 0.001 Deionized water qs Another skin oil and grease inhibiting creme is prepared having a composition described in Table II.
TABLE II
COMPONENT WEIGFIT
'~s Carbopol 1382~ (2~ Solids) 18.000 Cyclomethicone _ 6.000 Cetyl Alcohol 4.400 Spectron SA-13~ (Tridecyl Salicylate)4.000 Glycerin 3.000 Isoarachidyl Neopentanoate 2.400 Emulgade 1000 NI~ 1.750 willowbark Extract 1.500 Triethanolamine 99~ 1.420 C18-C36 Fatty Acid 1 .200 BRIJ 721m (Vegetable) 1.200 Arachidyl Behenate 1.000 Actiglyde-J Special~ 1.000 Polymethyl Methacrylate 1.000 Vitamin E Acetate - 1.000 Sodium Pyrolidone Carboxylate (50~ 0.750 solids) Algae Extract 0.500 DL-Panthenol 0.500 Silicone 200 (10 cst) 0.400 C1z-C=o Acid-PEG 8 Esters 0.400 Microat SF~ 0.360 Bernel Ester TOC~ 0.360 Glydant~ 0.300 Methylparaben 0.300 BRIJ 72c~ (Vegetable) 0.300 Polyethylene (A-C 400)~ 0.300 Shea Butter 0.200 Disodium EDTA 0.100 Amigel~ 0.100 Propylparaben 0.100 Vitamin A Palmitate 0.100 L-Lactic Acid 0.010 Biotin 0.001 Vitazyme C~ 0_001 Deionized Water qs WO 98!23257 - PCT/EP97I06693 -The present Example reports an in vitro analysis of sebum suppression by use of a salicylate ester.
3<n yitro Sebocvte Linoaenesis Assay Human sebaceous glands were isolated from the nose of a male (age 60) and cultured using submerged tissue culture techniques (Bajor et al, J. Invest. Dermatol. 102:1994. P.
564). These sebocytes accumulate intracellular lipid droplets characteristic of mature human sebum.
Harvested and passaged sebocytes were added to each well of a 48 well tissue culture plate and incubated at 37°C in the presence of 7.5~ COz for 10 days. The growth medium was changed three times per week. On the day of experimentation, the growth medium was removed and the sebocytes washed three times with phosphate buffered saline (PBS). Fresh PBS in 0.5 ml amount was added to each well and 10 microliters of active agent speculated to inhibit lipogenesis_ Triplicate wells were utilized for each sample. Controls consisted of PBS, dimethyl sulfoxide (DMSO) used to solubilize the lipophilic compounds, and phenol red, a compound which possesses estrogen-like activity. The cultures were incubated at 37°C/7.5~ COZ for minutes. Radioactive label was prepared by adding 30 100 ~t.l of 14-C labelled acetic acid (Amersham, sodium salt, specific activity of 56 mCi/mmol) to 10 ml of 50 mM sodium acetate buffer. Then 50 ~t.l was added to each well containing the sebocytes and active agents. The cultures were returned to the incubator for 4 hours. Thereafter the treatments and label were removed and the sebocytes rinsed WO 98!23257 PCT/EP97/06693 -three times with fresh PBS. Sebocytes were harvested and microliters removed and set aside for protein -assessment. The remaining samples containing the 14-C
label were extracted and the label counted using a Beckman 5 scintillation counter. Triplicates were performed for each sample.
For each 48 well tissue culture plate, 16 samples could be analyzed. Of these, 1 sample was reserved for 10 PBS, 1 sample for DMSO, and 1 sample for phenol red leaving 13 remaining samples.
TABLE I
Tridecv~.s~licvlate 9s Reduction standard Devi~.t3.on Concentration 0.00003 8.5 2.5 0.0003 13.3 1.0 0.003 28.3 2.1 0.01 44.7 9.7 0.03 49.1 6.3 0.05 48.9 8_5 0.1~ 63.0 7.7 WO 98/23257 PCTlEP97/06693 -TABLE II
Octvlsalicvlate ~ Reduction Standard Deviation Conc.
0.005 11.6 12.2 0.01 11.6 4.1 0.05 22.4 15.1 0.1~ 8.3 19.7 0.5~ 0 12.6 1.0~ 2.2 7.8 0.1~ Phenol Red 40.8 12.5 Salicylic Acid conc ~ Reduction Standard Deviation 0.00014 11.4 9.0 0.0014 10.1 10.5 0.014% 13.1 13.4 0.14 3.6 ~.4 Based on the results In Tables I, II and III, it is evident that tridecyl salicylate has significant activity in reducing oiliness and grease, especially compared to octylsalicylate and salicylic acid.
The foregoing description and examples illustrate selected embodiments of the present invention. Tn light thereof, various modifications will be suggested to one skilled in the art, all of which are within the spirit and purview of this invention.
Claims (3)
1. A cosmetic method for reducing or inhibiting skin production of oils and grease, the method comprising applying to the skin a safe and effective amount of salicylate ester in a pharmaceutically physiologically and/or cosmetically acceptable carrier, the salicylate ester having the formula (I):
wherein R is a C11-C30 alkyl or alkenyl radical.
wherein R is a C11-C30 alkyl or alkenyl radical.
2. The method according to claim 1 wherein the salicylate ester is a C12-C20 alkyl ester of salicylic acid.
3. The method according to claim 1 wherein the salicylate ester is tridecyl salicylate.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/774328 | 1996-11-27 | ||
| US08/774,328 US5773015A (en) | 1996-11-27 | 1996-11-27 | Method for controlling skin oils and grease |
| PCT/EP1997/006693 WO1998023257A1 (en) | 1996-11-27 | 1997-11-25 | Method for reducing skin oils and grease |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2243715A1 CA2243715A1 (en) | 1998-06-04 |
| CA2243715C true CA2243715C (en) | 2004-07-06 |
Family
ID=25100918
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002243715A Expired - Fee Related CA2243715C (en) | 1996-11-27 | 1997-11-25 | Method for reducing skin oils and grease |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5773015A (en) |
| EP (1) | EP0886517B1 (en) |
| JP (1) | JP3560985B2 (en) |
| KR (1) | KR100373282B1 (en) |
| AU (1) | AU721625B2 (en) |
| BR (1) | BR9707312A (en) |
| CA (1) | CA2243715C (en) |
| DE (1) | DE69713743T2 (en) |
| ES (1) | ES2178790T3 (en) |
| MX (1) | MX9806031A (en) |
| WO (1) | WO1998023257A1 (en) |
| ZA (1) | ZA9710590B (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU4233297A (en) * | 1996-08-23 | 1998-03-06 | Arch Development Corporation | Identification of activators and inhibitors of sebum formation |
| JP3422468B2 (en) * | 1998-02-24 | 2003-06-30 | 花王株式会社 | Sebum selective removal method |
| US6120756A (en) * | 1998-08-19 | 2000-09-19 | Philip I. Markowitz | Topical anionic salicylate for disorders of the skin |
| WO2000074642A1 (en) | 1999-06-03 | 2000-12-14 | Unilever Plc | Anti-sebum skin care cosmetic compositions containing branched esters |
| US6355261B1 (en) | 1999-12-02 | 2002-03-12 | The C. P. Hall Company | Ultraviolet radiation absorbing waxes useful in cosmetic compositions |
| JP2002284705A (en) | 2001-01-19 | 2002-10-03 | Shiseido Co Ltd | Torpent |
| WO2002067889A2 (en) * | 2001-02-22 | 2002-09-06 | Unilever Plc | Skin composition for reducing skin oils and grease |
| JP2002293714A (en) * | 2001-03-30 | 2002-10-09 | Fancl Corp | Skin cosmetic |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2338034A1 (en) * | 1976-01-14 | 1977-08-12 | Oreal | NEW COSMETIC PROCESS TO IMPROVE THE APPEARANCE OF OILY HAIR AND / OR OILY SKIN |
| JPS5762212A (en) * | 1980-10-01 | 1982-04-15 | Mitsui Toatsu Chem Inc | Cosmetic |
| US4891228A (en) * | 1988-02-02 | 1990-01-02 | Richardson-Vicks Inc. | Medicated cleansing pads |
| US4891227A (en) * | 1988-02-02 | 1990-01-02 | Richardson-Vicks Inc. | Medicated cleansing pads |
| US5262407A (en) * | 1988-12-16 | 1993-11-16 | L'oreal | Use of salicylic derivatives for the treatment of skin aging |
| JPH0436238A (en) * | 1990-06-01 | 1992-02-06 | Takasago Internatl Corp | External skin drug for acne vulgaris |
| JPH07501540A (en) * | 1991-11-25 | 1995-02-16 | リチャードソン、ビックス、インコーポレーテッド | Composition for regulating skin wrinkles and/or skin atrophy |
| EP0614354B1 (en) * | 1991-11-25 | 2001-01-17 | Richardson-Vicks, Inc. | Use of salicylic acid for regulating skin atrophy |
| AP486A (en) * | 1993-04-27 | 1996-04-16 | Pfizer | Indole derivatives. |
| FR2718022B1 (en) * | 1994-04-01 | 1996-04-26 | Roussel Uclaf | Cosmetic or dermatological compositions and their preparation. |
| FR2725898B1 (en) * | 1994-10-24 | 1996-12-13 | Oreal | PRODUCT FOR TOPICAL APPLICATION CONTAINING A LIPASE AND A HYDROXYACID PRECURSOR |
| WO1997030690A1 (en) * | 1996-02-23 | 1997-08-28 | Unilever Plc | Skin treatment with salicylic acid esters |
| US5690948A (en) * | 1997-01-10 | 1997-11-25 | Elizabeth Arden Co., Division Of Conopco, Inc. | Antisebum and antioxidant compositions containing guguliped and alcoholic fraction thereof |
-
1996
- 1996-11-27 US US08/774,328 patent/US5773015A/en not_active Expired - Lifetime
-
1997
- 1997-11-25 CA CA002243715A patent/CA2243715C/en not_active Expired - Fee Related
- 1997-11-25 BR BR9707312A patent/BR9707312A/en not_active IP Right Cessation
- 1997-11-25 KR KR10-1998-0705753A patent/KR100373282B1/en not_active IP Right Cessation
- 1997-11-25 ZA ZA9710590A patent/ZA9710590B/en unknown
- 1997-11-25 DE DE69713743T patent/DE69713743T2/en not_active Expired - Lifetime
- 1997-11-25 EP EP97952829A patent/EP0886517B1/en not_active Expired - Lifetime
- 1997-11-25 ES ES97952829T patent/ES2178790T3/en not_active Expired - Lifetime
- 1997-11-25 JP JP52430098A patent/JP3560985B2/en not_active Expired - Fee Related
- 1997-11-25 WO PCT/EP1997/006693 patent/WO1998023257A1/en active IP Right Grant
- 1997-11-25 AU AU56568/98A patent/AU721625B2/en not_active Ceased
-
1998
- 1998-07-27 MX MX9806031A patent/MX9806031A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2243715A1 (en) | 1998-06-04 |
| BR9707312A (en) | 1999-07-20 |
| JP2000504349A (en) | 2000-04-11 |
| JP3560985B2 (en) | 2004-09-02 |
| EP0886517A1 (en) | 1998-12-30 |
| ZA9710590B (en) | 1999-05-25 |
| US5773015A (en) | 1998-06-30 |
| DE69713743D1 (en) | 2002-08-08 |
| WO1998023257A1 (en) | 1998-06-04 |
| AU5656898A (en) | 1998-06-22 |
| AU721625B2 (en) | 2000-07-13 |
| DE69713743T2 (en) | 2002-11-07 |
| ES2178790T3 (en) | 2003-01-01 |
| MX9806031A (en) | 1998-11-30 |
| EP0886517B1 (en) | 2002-07-03 |
| KR19990082033A (en) | 1999-11-15 |
| KR100373282B1 (en) | 2003-07-16 |
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