GB2208268A

GB2208268A - Hydroperoxide for use in the treatment of acne and seborrhoea

Info

Publication number: GB2208268A
Application number: GB8817862A
Authority: GB
Inventors: Michel Hocquaux; Didier Semeria; Didier Saint-Leger; Philippe Vingler
Original assignee: LOreal SA
Current assignee: LOreal SA
Priority date: 1987-07-28
Filing date: 1988-07-27
Publication date: 1989-03-22
Anticipated expiration: 2008-07-27
Also published as: FR2618672B1; DE3825536A1; JPS6447716A; GB8817862D0; CA1307467C; FR2618672A1; GB2208268B

Description

A1 - USE OF A HYDROPEROXIDE IN THE TREATMENT OF ACNE AND SEBORRHOEA The

present invention relates to the use of a hydroperoxide as active principle in the treatment of acne and seborrhoea.

el U., C 2 /- ' 2'6 o Acne, Like seborrhoea, results from a hypersecretion of the sebaceous glands.

The principal consequence of seborrhoea is to make the hair greasy, which has an adverse effect on the attractive appearanc e of the hair.

Acne,- in contrast, manifests itself more especiatty on the face of relatively young subjects, by the formation of a characteristic lesion, the comedo.

The Latter results from the obstruction of the pitosebaceous duct as a consequence of a dyskeratinization of the region of the infunclibutum of the duct.

This modification perinits the hyperprotiferation of the cutaneous resident strains, mainly Propionibacterium a c n e s The consequence of this bacterial hyperprotifer- ation is to release into the surrounding area certain proteases of bacterial origin, which cause a Lysis of the foLticutar sac and thus the release of inflammatory com pounds within the dermis, and trigger the body's infLam matory type reaction.

The principle features of the pathology of acne are hence:

an increase in sebaceous excretion, W I.

2 - - a disorder of the keratinization of the pilo sebaceous duct, and - a bacterial hyperprotiferation, mainly of Prop ionibacterium acnes.

A good anti-acne agent capable of treating acne effectively must hence possess:

a) a keratoLytic and comedolytic activity for the purpose of avoiding hyperkeratosis of the follicles and of enabling the comedones to be eliminated, b) a bacteriostatic action for the purpose of inhibiting the action of Propionibacterium acnes, and c) a sebostatic activity for the purpose of in hibiting the hyperseborrhoea.

Amongst compounds which have hitherto been used as anti-acne agents, the best known is probably benzoyl peroxide, which possesses not only keratolytic but also comedolytic properties.

This peroxide is not, however, free from certain side effects during treatment, such as irritations, even when it is employed at relatively low concentrations.

According to the present invention, it has now been shown that certain hydroperoxides possess a keratolytic, comedolytic and bacteriostatic activity superior to that of benzoyl peroxide without, howevert 25. exhibiting the same drawbacks. in particular the phenomenon of skin irritation.

P j i I 1 v, 1 R e Moreover, it has been found that the hydroperoxides according to the invention have an especially marked anti-dandruff activity without causing intolerance effects, in particular itching of the scalp.

Accordingly, one subject of the present invention is a hydroperoxide of the general formula:

R 11 R 3 c OOH 2 (I) in which 1 and R 2' which may be identical or different, are each a hydrogen atom or a C 1-4 alkyl radical; 3 is a linear or branched alkyl radical having from 1 to 21 carbon atoms. a linear or branched alkenyl radical having from 2 to 17 carbon atoms,, an alkadienyl radical having from 4 to 17 carbon atoms, an alkoxyalkyl radical having from 2 to 19 carbon atoms, a polyalkoxyalkyl radical having from 4 to 31 Carbon atoms, or a saturated or unsaturated cycloalkyl radical having from 4 to 6 carbon atoms, optionally substituted, or R 1 and R 3' taken together with the carbon atom to which they are attached, form a saturated or unsaturated non-aromatic ring having from 4 to 6 carbon atoms, the sum of the carbon atoms of R 1 +R 2 +R 3 beingl 3; for use in the treatment of acne or seborrhoea.

Examples of a C 1-4 alkyl radical include methyl, 1 1; tr - 4 ethyl, propyl, isopropyl and butyl radicals.

According to one embodiment of the invention, the hydroxperoxides are of the primary type (R,=R 2 =H) and R 3 is a linear or branched fatty chain having from 7 to 17 carbon 5 atoms.

Various pharmacological studies carried out on the hydroperoxides according to the invention have demonstrated that they exhibit good penetration as a result of their marked lipophilic nature, as well as good keratolytic and comedolytic activity, whilst lacking the known drawbacks of benzoyl peroxide.

The studies have also demonstrated that the hydroperoxides exhibit good antiseborrhoeic activity.

- The hydroperoxides as defined above are chemically more stable and pharmacologically more active than peroxides in general, especially benzoyl peroxide.

Examples of hydroperoxides of formula (I) include:

1-tert-butyl-hydroperoxide 1-pentyl hydroperoxide 1-hexyl hydroperoxide 2hexyl hydroperoxide 1 1 1 I 4 t, 1 J11 - 3-hexyl hydroperoxide 1-heptyl hydroperoxide 1-octyl hydroperoxide 2- octyl hydroperoxide 1-decyl hydroperoxide 1-dodecyl hydroperoxide 2- dodecyl hydroperoxide 1-tetradecyl hydroperoxide 2-tetradecyl hydroperoxide 1-pentadecyl hydroperoxide 1-hexadecyl hydroperoxide 4- hexadecyl hydroperoxide 1-octadecyl hydroperoxide 1-methylhex-l-yl hydroperoxide 2-ethylhex-l-yl hydroperoxide 1,1-dimethyloct-l-yl hydroperoxide 1,1-dimethylnon-l-yl hydroperoxide 2,6,10,14- tetramethylpentadec-l-yL hydroperoxide 4-hexen-lyl hydroperoxide 6nonen-l- yl hydroperoxide 9-decen-l-yl hydroperoxide 10-undecen-l-yl hydroperoxide ll-tetradecen-l-yt hydroperoxide llhexadecen-l-yl hydroperoxide 9- octadecen-l-yl hyd roperoxide 3,7-diinethyl-6-octen-l-yl hydroperoxide 3, 5-hexadien-l-yl hydroperoxide as 4,8-undecadien-l-yl hydroperoxid 8,10-dodecadien-l-yl hydroperoxide 2- inethoxyeth-l-yt hydroperoxide 2-ethoxyeth-l-yl hydroperoxide 2-(2- methoxyethoxy)eth-l-yt hydroperoxide 2-(2-ethoxyethoxy)eth-l-yl hydroperoxide 2-(2-butyloxyethoxy)eth-l-yt hydroperoxide cyclohexyl hydroperoxide 1-isopropyleyclohex-l-yl hydroperoxide 2-methyl-2- cyclobuten-l-yl hydroperoxide 2-cyclopenten-l-yt hydroperoxide 3- cyclohexen-l-yt hydroperoxide 8-menthyl hydroperoxide, and 1-menthen-9-yl hydroperoxide. Examples of hydroperoxides which have led to satisfactory results both in tests relating to anti-acne activity and in anti- seborrhoeic tests, include: 1-tert-butyl hydroperoxide 1-hexyL hydroperoxide 1-octyl hydroperoxide 2-octyt hydroperoxide 1-decyl hydroperoxide 1-dodecyl hydroperoxide 2-dodecyl hydroperoxide 1tetradecyL hydroperoxide 1-hexadecyl hydroperoxide il 2-ethyLhex-1-yL hydroperoxide 6-nonen-1-yL hydroperoxide 9-decen-1-yL hydroperoxide 10-undecen-1-yL hydroperoxide 11-tetradecen-1-yL hydroperoxide 11-hexadecen-1-yL hydroperoxide 9-octadecen-l-yL hydroperoxide 3,7-dimethyL-6-octen-I-yL hydroperoxide 8,10-dodecadien-1- yL hydroperoxide 2-(2-ethoxyethoxy)eth-1-yL hydroperoxide and 1-menthen-9-yL hydroperoxide A further subject of the present invention is the use of hydroperoxides of formula (I) in the preparation of a dermatological or hair care composition for the treatment of acne or seborrhoea. The invention also provides anti-acne and anti- seborrhoea compositions comprising, in a carrier, diluent or adjuvant, at least one hydroperoxide of formula (I).

The hydroperoxides of formula (I) are in some cases already described in the literature.

The new hydroperoxides may be obtained according to known methods, for example in a two stage process as described in "Organic Peroxides" Vol. 2 pages 1-151 Ed. Swern (Interscience Publishers New York 1971).

According to this method, a sulphonate, or a brosylate, (which is more reactive), of the corresponding alcohol is prepared.

L r Brosylates are obtained by the action of 4-bromobenzenesulphonic acid chloride on the corresponding alcohol in the presence of pyridine, according to the following reaction scheme:

f ip R 1 1 R - C - OH + C1502- & Br + C 5 H 5 N 1 2 P + R 3 - C - OS02-Br + C5EsNE, Cl 1 2 By nucLeophiLic substitution of the brosyLate with the NO 2 anion, formed in situ by the action of potass- - ium hydroxide on hydrogen peroxide, the expected hydroperoxide is obtained.

R c 0S02---(B r 3 1 C OOR + Br -& so 2 OK R 2 1 12 + H 2 0 The tatter reaction is suitably performed in a methanollwater or methanolltert-butanollwater mixture.

The yields of hydroperoxide are variable, since they depend on the nature of the starting alcohol.

The compositions may be presented in various forms, for example in the form of an ointment, a gel, an emulsion, a lotion, a shampoo, or a stick.

The term "ointment" covers formulations such as is creams comprising absorbable lipophilic bases, for example petroleum jelly, lanol-in, pulyethylene glycols and also mixtures thcreof.

The emulsions can be of the oit-in-water or waterin-oil type, and prepared by dispersing the hydroperoxide in the aqueous phase before emuLsif ication.

The ratio by weight o! the fatty phase to the aqueous phase is generaLLy from 95:5 to 25:75.

Among the different oiLs capabLe of forming the 5 fatty phase, various products may be used, such as: - animaL oiLs such as, for exampLe, LanoLin, perhydrosquaLene, vegetabLe fats such as sweet aLmond oiL, avocado oiL, castor oiL, oLive oiL, grape-pip oiL, poppy seed oiL, rape seed oiL, groundnut oiL, maize oiL, sunfLower oiL, hazeLnut oiL, jojoba oiL, saffLower oiL, wheatgerm oiL, shea butter and Shorea robusta grease, mineraL oiLs such as, for exampLe, Liquid paraffin, and siLicone oiLs which are soLubLe in other oiLs.

It is aLso possibLe to use fatty aLcohoLs, such as cetyL aLcohoL, or certain synthetic products such as saturated or unsaturated esters,.for example isopropyl palmitate, isopropyl, butyl or cetyl myristate, hexadecyL, gLyceroL and poLyethyLene gLycot stearates, ethyL paLmitate, decyL oLeate, as weLL as trigLycerides of C8- C12 acids and cetyL ricinoLeate, purceLLin oiL and hydrogenated poLyisobutyLene.

The fatty phase can aLso contain certain waxes, for example carnauba wax, beeswax, ozokerite, can- deLiLLa wax or poLyethyLene wax.

The compositions in the form of emuLsions can aLso contain other ingredients, such as preservatives, W 1 l> sequestering agents, pigments, perfumes, sunscreens, coLouringsf emuLsion stabiLizers such as magnesium suLphate, and fiLters such as taLc, powdered nyLon, powdered starch or powdered poLyethyLene.

The excipients-and in qr.edients are such that they cannot react with the hydroperoxicles.

The geLs are semi-soLid preparations obtained by geLLing a suspension of the hydroperoxicle using a geLLing agent, such as "bentone geL" soLd by the company N. L. INDUSTRIES, for a fatty phase or for an aqueous phase, crossLinked poLyacryLic acid, such as those soLd by the company GOODRICH under the names CARBOPOL 940 and - 941 and used in neutraLized form, or aLternativeLy ceLLu- -Lose derivatives.

It is possibLe, if so desired, to introduce a nonionic surfactant into the geL, such as, for exampLe, a poLyoxyethylenated aLcohoL containing from 4 to 20 ethyLene oxide units or sorb-itan esters, thereby permit ting better dispersion and avaiLabiLity of the hydroperoxicle.

It is aLso possibLe to incorporate a soLvent such as a Lower aLit)hatic aLcohoL, for exarnpLe ethanoL, in a proportion of from 0.5. to 30% by Amieight, a preservative, a perfume. and aLso a coLouring.

The compositions can aLso contain a humectant agent in a proportion of 1 to 20%, such as, for exampLe, gLycerin, sorbitoL or propyLene gLycoL.

In the compositions as described above, the hydroperoxide of formula (1) is generally present at from 0.01 to 20% by weight, for example from 0.05 to 10% by weight, relative to the total weight of the composition.

In one embodiment, the hydroperoxide may be used with an anti-acne substance that can be applied topicallyr or with an antibiotic substance such as erythromycin, clindamycin or lincomycin, their esters and their salts.

In another embodiment, the hydroperoxide of formula (I) may be combined with a keratolytic substance such as, for example, salicylic acid, an antiseptic agentr an antifungal agent such as an imidazole derivative, for example miconazole, or an anti-inflammatory agent.

When the hydroperoxides of formula (I) are intended for the treatment of seborrhoea, the compositions may be presented in the form of a lotion or a shampoo, and generally contain at least one detergent which is anionic, cationic, nonionic or amphoteric.

Suitable anionic agents include alkyl sulphates, alkyl ether sulphates, alkyl polyether sulphates, alkylsulphonates (the alkyl radicals having from 8 to 18 carbon atoms), sulphated monoglycerides, sulphonated monoglycerides, sulphated alkanolamides, sulphonated alkanolamides, fatty acid soaps, fatty alcohol monosulphosuccinates, the condensation products of fatty acids with isethionic acid, the condensation products of fatty acids with methyltaurine, the condensation products of fatty acids with sarcosine and the condensation products g c - 1.3 - of fatty acids with a protein hydrolysate.

Suitable cationic detergents include long-chain quaternary ammonium compounds, esters of fatty acids and amino alcohols, and also polyether amines.

Suitable nonionic detergents include esters of polyols and sugars, the condensation products of ethylene oxide with fatty acidsp with fatty alcohols, with long-chain alkylphenols, or with long-chain amides, or alternatively polyglycerolated fatty alcohols.

Suitable amphoteric detergents include asparagine derivatives, the condensation products of monochloroacetic acid with imidazolines, and alkylaminopropionates.

When a surfactant is present, its concentration is generally from 3 to 50%, for example from 5 to 25%, by weight relative to the total weight of the composition.

The shampoos may also contain thickeners, such as fatty acid alkanolamides, cellulose derivatives such as carboxymethy1cellulose or hydroxymethy1cellulose, or alternatively natural gums.

A further subject of the present invention is a method of cosmetic treament of acne or seborrhoea which comprises applying to the skin or hair a hydroperoxide of formula M.

In the treatment of acne, compositions based on at least one hydroperoxide of formula (I) are suitably applied at least once daily on the lesions on the basis of 1 0.5 to 10 mg/CM2, it being possible for the treatment period to be of the order of 2 to 14 weeks, depending on the extent of the skin condition.

In the treatment of seborrhoea, it is usual to employ the hydroperoxides in the form of lotions or shampoos, which are generally applied on the whole head of hair at least twice per week over a period of several weeks.

The following Examples, of the preparation of the hydroperoxides and of anti-acne and antiseborrhoeic compositions, further illustrate the invention.

PREPARATION EXAMPLES EXAMPLE 1 Preparation of 3,7-dimethyl-6-octen-l-yl hydroperoxide a) Preparation of 3,7-dimethyl-6-octen-l-yl brosylate 9.5 9 (6.09 x 10-2 mol) of 3,7-dimethyl-6-octen1-ol are solubilized in 80 ml of pyridine, dried over potassium hydroxide, in a three-necked flask equipped 2G with a mechanical stirrer, a thermometer and a condenser surmounted by a calcium chloride guard tube.

The reaction-inixture is cooled in an ice bath at o0C.

15.56 9 (6.09 x 10-2 moL) of brosyL chloride S 1 (22 OOL X ú) aueq4awojolq3P q4P4 UO;2ej4xa ia;V (JaleR O]W OOL U 13H qZBUaJ45 %9ú 1W OL) uo;nlos p3e 3J01q3OJP.xq olut painod s uoinlos paloo3 aq.L -sinoq 2L J01 paiit;s SL wnLPE1W UOL;3eaJ aq4 JapxojpAq wnsse4od aqI O UO; PPe a44 Ja41V sinoq om; XiaAa suot4jod lent)a ino u pappe aie (;ualeAnba =) UOInlos apxojpXq wnsselod snoanbe 44BuaJ45 %02 O lw 5641 3 Osú 04;4Bnoiq lwnpaw uo;ne ai a44 04 pappe aie apxojad uaBoipAq,loA o (s;ualeAnba 47 =) lw 21 JOUe44aW O 1W 29 UL PaAlOSSLP aie azelAsojq 1A-L -ua;20-9-1xq;awP-Loú O (low OL X LLo 6 ú9,9 apxojadojpX4 IA-L-ua;2o-9-1Xq;awn-i' (q Mú:PMA) paue;qo aie a;eIXsoiq o 6 LO.1 J;UaAlOS a41 jo uo;ejodeAa PUe (0:09 aueq4awOJ0143P jauejuad:;uenla) lab enls uo uozej;l ia;V "paue;qo s lo apnjn ssal OL -jnolo2 e J4UaAlOS aq; ko uo;ejodeAa pue a;e4dlns wnpos JaAO BuXJP 'Hd jejInau ol ia;em M;m aseqd n[ueSio a41 o BUqSes 0(1w OOL x Z) aue44awOJ0142[" P 44m UO43ej;xa Ja4Y (OZH 1W 002 U 13H 4;rWaJls %9ú lw 050 uo;nlos ppe 3jol42ojpA4 o;u painod S ai n;xw uo;3eaj a41 -sino4 o asino2 a4; u ain;e - jadwal wooi o; uin;aj o; pamolle s[ ain;xw aqI -300;e paue;uew s wnpaw uo; oeaj a44 o ainjejadwa; a4; alq#4 suo;jod llews u pappe aie 9Z 02 SL - 16 the organic phase is washed with water to neutrality and then dried over sodium sulphate. After evaporation of the solvent in the cold and under vacuum, the crude oil is purified by chromatography on silica get (eluant: pentaneldichloromethane 60:40).

After evaporation of the solvent in the cold and under vacuum, 1.63 9 of pure hydroperoxide are obtained (Yield: 48%).

250 MHz1H NMR spectrum in agreement with the structure.

Peroxide value: 98.5%.

TLC: silica gel eluant CH2C12 Pink single spot - characteristic of hydroperoxides [E. KNAPPE D. PETERI, Z. Anal. Chem. 190, 386, (1962M. EXAMPLE 2 Preparation of 6-nonen-l-yL hydroperoxide a) 6-Nonen-l-yl brosylate The brosylate is prepared as described in Example la, starting with 6-nonen-l-ol, in a 50% yield.

b) 6-Nonen-l-yl hydroperoxide According to the procedure described in Example lb, 920 mg of a colourless oil are obtained from 4 9 of brosylate (Yield: 54%).

250 MHz1H NMR in agreement with the structure.

Peroxide value: 95.9%.

TLC: silica gel 4 - 17 etuant: CH2C12 Pink single spot - characteristic of hydroperoxides. EXAMPLE 3 Preparation of 9-decen-l-yl hydroperoxide a) 9-Decen-l-yl brosytate, The brosytate is prepared as described in Exampte la, starting with 9-decen-l- ol, in a 35% yield. b) 9-Decen-l-yl hydroperoxide According to the procedure described in Example lb, 1.64 g of a colourless oil are obtained from 5 9 of brosylate (Yield: 59%). 90 MHz 1 H NMR in agreement with the structure. Peroxide value: 97%. TLC: silica get is eLuant: CH2CL2 Pink single spot - characteristic of hydroperoxides.

EXAMPLE 4

Preparation of 10-undecen-1-yL hydroperoxide a) 10-Undecen-1-yL brosyLate The brosyLate is prepared as described in Example la, starting with undecenyL alcohol, in 43% yield.

b) 10-Undecen-1-yL hydroperoxide According to the procedure described in Example 1b, 3.9 g of a coLourLess oil are obtained from 19.6 g of the brosyLate (Yield: 42%). 90 MHz 1 H NMR in agreement with the structure. TLC: silica get i eluant: CH2C12 Pink single spot - characteristic of hydroperoxides.

EXAMPLE 5

Preparation of 11-tetradecen-l-yl hydroperoxide a) 11-Tetradecen-l-yl brosylate The brosylate is prepared as described in Example la, starting with 11-tetradecen-l-ol, in a 50% yield.

b) 11-Tetradecen-lyL hydroperoxide According to the procedure described in Example lb, 1.35 9 of a colourless oil are obtained from 4.75 9 of the brosylate (Yield: 54%).

250 MHz1H NMR in agreement with the structure.

Peroxide value: 98%.

TLC: silica gel is eluant CH2C12 Pink single spot - characteristic of hydroperoxides.

EXAMPLE 6

Preparation of 11-hexadecen-l-yl hydroperoxide a) ll-Nexadecen-l-yl brosylate The brosylate is prepared as in Example la, start ing with 11-hexadecen-l-ol, in an 83% yield.

b) 11-Hexadecen-l-yl hydroperoxide According to the procedure described in Example lb, 1.2 g of a colourless oil are obtained from 4.35 9 of brosylate (Yield: 50%). 80 MHz1H NMR in agreement with the structure. Peroxide value: 97.8%.

1 l 1 1 1 1 l TLC: silica gel eLuant CH2CL2 Pink single spot characteristic of hydroperoxides. EXAMPLE 7 Preparation of_8,10-dodecadien-1-yL hydroperoxide a) 8,10-Dodecadien-1-yL brosyLate The brosylate is prepared as in Example la, starting with 8,10-dodecadienl-ol, in a 67% yield.

b) 8,10-Dodecadien-l-yl hydroperoxide According to the procedure described in Example lb, 550 mg of a colourless oil are obtained from 6.36 9 of the brosylate (Yield: 10%).

MHz 1 H NMR in agreement with the structure.

Peroxide value: 97%.

TLC: silica gel eluant CH2C12 Pink single spot - specific to hydroperoxides. EXAMPLE 8 Preparation of 1-menthen-9-yl hydropero,xide a) 1-Menthen-9-yl brosylate The brosylate is prepared as in Example la, starting with 1-menthen-9-ol, in a 42% yield.

b) 1-Menthen-9-yt hydroperoxide According to the procedure described in Example lb, 890 mg of a colourless oil are obtained from 6.3 9 of the brosylate (Yield: 31%).

250 MHz1H NMR in agreement with the structure.

1 - 20 is Peroxide value: 90.9% TLC: silica get eLuant CH2C12 Pink spot characteristic of hydroperoxides. EXAMPLE 9 Preparation of 2-(2-ethoxyethoxy)eth-l-yl hydroperoxide a) DiethyLene glycol monoethyl ether brosylate The brosytate is prepared as in Example la, starting with diethylene glycol monoethyL ether, in an 83% yield b) 2C2-Ethoxyethoxy)eth-l-yt hydroperoxide According to the procedure described in Example lb, 3.82 9 of a colourless oil are obtained from 20 9 of the brosylate (Yield: 45%). 250 MHz1H NMR in agreement with the structure. Peroxide value: 95% TLC: silica get eluant: dichloromethanelmethanol (9515) Pink single spot - characteristic of hydroperoxides. EXAMPLE 10 Preparation of 2-dodecyl hydroperoxide a) 2-Dodecanyl brosylate The brosYlate is prepared as in Example la, start ing with 2-dodecanol, in a 60.5% yield.

b) 2-Dodecyl hydroperoxide According to the procedure described in Example lb, 1.05 9 of a colourless oil are obtained from 12 g of the brosylate (Yield: 18%).

W c - 21 1 () 250 MHzlH NMR in agreement with the structure.

Peroxide vaLue: 98% TLC: siLica geL eLuant CH2CL2 Pink singLe spot characteristic of hydroperoxides.

EXAMPLES OF COMPOSITIONS EXAMPLE 1 Anti-acne geL CarboxyvinyL poLymer soLd by the company GOODRICH under the name "CARBOPOL 940".

DiethyLene gLycoL ethyL ether............

PoLyethyLene gLycoL 400 DiisopropanoLamine EthyLenediaminetetraacetic acid 3,7-DimethyL-6-octen-1-yL hydroperoxide..

Water 10 9 EthanoL, 900 strength, qs 100 g EXAMPLE 2 Anti-acne geL PoLyethyLene gLycoL 400 HydroxypropyLceLLuLose IsopropanoL EthyLenediaminetetraacetic acid 1-DodecyL hydroperoxide OctyLdodecanoL Citric acid EthanoL, 900 strength, qs EXAMPLE 3 Anti-acne geL DiethyLene gLycoL ethyL ether 1 9 20 9 5 9 0.1 9 0.05 g 0.15 9 ..... 100 g 9 1.5 9 9 0.05 g 1 g 9 0.05 g ........... 20 9 (i EthyLenediaminetetraacetic acid 0.01 9 9-Octadecen-1-yL hydroperoxide 0.05 g HydroxyethyLceLLuLose 1 9 Citric acid 0.05 g Water 40 g EthanoL, 900 strength, qs 100 g EXAMPLE 4 Anti-acne cream of the oiL-in-water type Mixture of gLyceroL monostearate and poLyethyLene gLycoL monostearate, soLd by the company ATLAS under the name "ARLATONE 983 s" 5 g CetyL aLcohoL 3 g PerhydrosquaLene 10 g GLyceroL monostearate 2.5 g ButyLated hydroxyanisoLe 0.05 g ButyLated hydroxytoLuene 0.05 g TrigLycerides of capryLic and capric acids, soLd by the company DYNAMIT NOBEL under the name "MIGLYOL 812............. 10 9 GLycerin 5 g Citric acid 0.02 g 1-OctyL hydroperoxide 1 9 Water qs 100 g EXAMPLE 5 Anti-acne cream of the water-in-oiL type Mixture of fatty acid saLts and esters, soLd by the company HENKEL under the name "DEHYMULS F............................. 8 g i j C 01 is Decyt oleate...... Liquid paraffin... White vasetine.... Triglycerides of caprylic and capric a c i d s Glycerin Magnesium sulphate. 7H20 Preservative Perfume 1-Menthen-9-yL hydroperoxide Water qs EXAMPLE 6 Anhydrous anti-acne ointment Thick vaseLine 29.5 g Fluid paraffin oil 25 g LauryL aLcohoL poLyoxyethyLenated with 4 moles of ethylene oxide, sold by the company ICI under the name "BRIJ 30..... 5 g PoLyethyLene wax 10 g TrigLycerides of capryLic and capric acids 30 g 1-HexadecyL hydroperoxide 0.5 g EXAMPLE 7 Anti-acne Lotion Polyethylene glycol 400 40 g IsopropanoL 30 g Citric acid 0.1 g 5-PhenyLpent-1-yL hydroperoxide 0.2 9 OctyLdodecanoL qs 100 g 8 g 5 g 20 g g 5 9 0.5 9 0.05 0.1 9 1 9 100 9 EXAMPLE 8 ALcohot antiseborrhoeic lotion EXAMPLE

IsopropanoL 74.8 TrigLycericles of capryLic and capric acids, soLd by the company DYNAMIT NOBEL under the name "MigLyoL 812............. 10 g Compound of formuLa -C-Si(CH3)2-0-3-4 soLd by the company UNION CARBIDE under the name "CYCLOMETHICONE 7207".. 1-DodecyL hydroperoxicle..... 9 Antiseborrhoeic shampoo Ammonium LauryL ether suLphate containing 30% of active substance 55 g Sorbitan monoLaurate poLyoxyethyLenated with 20 moLes of ethyLene oxide, soLd by the company ICI under the name "TWEEN 20" 4.5 9 Sorbitan Laurate soLd by the company ICI under the name "SPAN 20................. 2 g GLyceryL cocoate containing 7 moLes of ethyLene oxide, soLd by the company HENKEL under the name "CETIOL HE............... 2.5 g Coconut fatty acid cliethanoLamicles soLd by the company KENKEL under the name "COMPERLAN KD...................................... 2 g 1-OctyL hydroperoxicle 0.1 9 Water qs............................... 100 9 9 0.2 g C p

Claims

A hydroperoxide of the general formula:

R 11 R 3 - c - WH k (I) in which:

R 1 and R 27 which may be identical or different, are each a hydrogen atom or a C 1-4 alkyl radical, R 3 is a linear or branched alkyl radical having from 1 to 21 carbon atoms, a linear or branched alkenyl radical having from 2 to 17 carbon atoms, an alkadienyl radical having from 4 to 17 carbon atoms, an alkoxyalkyl radical having from 2 to 19 carbon atoms, a polyalkoxyalkyl radical having from 4 to 31 carbon atoms, or a saturated or unsaturated cycloalkyl radical having from 4 to 6 carbon atoms, optionally substituted, or R 1 and Rj, taken together with the carbon atom to which they are attached, form a saturated or unsaturated non-aromatic ring having from 4 to 6 carbon atoms, the sum of the carbon atoms of R 1 +R 2 +R 3 being > 3; for use in the treatment of acne or seborrhoea.
2. A hydroperoxide according to claim 1 wherein R 1 and R2 are both a hydrogen atom and R3 is a linear or branched fatty chain having from 7 to 17 carbon atoms.
3.

2, which is: 1-tert-butyl hydroperoxide 1-pentyl hydroperoxide 1-hexyl 2hexyL 3-hexyl 1-heptyl 1 1 A hydropgroxide_according to claim 1 or hydroperoxide hydroperoxide hydroperoxide hydroperoxide 1-octyl h, ydroperoxide 2-octyl hydroperoxide 1-decyl hydroperoxide 1-dodecyt hydroperoxide 2-dodecyt hydroperoxide 1-tetradecyl hydroperoxide 2tetradecyt hydroperoxide 1-pentadecyl hydroperoxide 1-hexadecyl hydroperoxide 4-hexadecyl hydroperoxide 1-octadecyl hydroperoxide 1methythex-l-yl hydroperoxide 2-ethylhex-l-yl hydroperoxide 1,1dimethyloct-l-yl hydroperoxide 1,1-dimethylnon-l-yl hydroperoxide 2,6,10, 14-tetramethylpentadec-l-yL hydroperoxide 4-hexen-l-yL hydroperoxide 6nonen-l-yL hydroperoxide I (k b 9-decen-l-yL hydroperoxide 10-undecen-l-yL hydroperoxide ll-tetradecen-l- yl hydroperoxide 11-hexadecen-l-yL hydroperoxide 9-octadecen-l-yL hydroperoxide 3,7-dimethyl-6-octen-l-yl hydroperoxide 3,5-hexadien-l-yL hydroperoxide 4,8-undecadien-l-yt hydroperoxide 8,10-dodecadien-l-yl hydroperoxide 2-methoxyeth-l-yl hydroperoxide 2-ethoxyeth-l-yL hydroperoxide 2-(2-methoxyethoxy)eth-l-yL hydroperoxide 2-(2- ethoxyethoxy)eth-l-yl hydroperoxide 2-(2-butyLoxyethoxy)eth-l-yl hydroperoxide cyclohexyL hydroperoxide 1-isopropytcyclohex-l-yl hydroperoxide 2-methyl-2-cyclobuten-l-yL hydroperoxide 2-cycLopenten-l-yL hydroperoxide 3-cycLohexen-l-yl hydroperoxide 8-menthyL hydroperoxide, or 1-menthen-9-yl hydroperoxide
4. A hydroperoxide according to claim 3 which is:

1-tert-butyl hydroperoxide 1-hexyl hydroperoxide 1-octyl hydroperoxide (1 - 28 2-octyt hydroperoxide 1-decyl hydroperoxide 1-dodecyt hydroperoxide 2-dodecyl hydroperoxide 1-tetradecyl hydroperoxide 1-hexadecyl hydroperoxide 2-ethylhex-l-yl hydroperoxide 6-nonen-l-yt hydroperoxide 9-decen-l-yL hydroperoxide 10-undecen-l-yL hydroperoxide ll-tetradecen-l-yL hydroperoxide 11-hexadecen-l-yL hydroperoxide 9-octadecen-l-yl hydroperoxide" 3,7-dimethyl-6-octen-l-yL hydroperoxide 8,10-dodecadien-l-yL hydroperoxide 2-(2-ethoxyethoxy)eth-l-yL hydroperoxide, or 1-menthen-9-yl hydroperoxide 1
5. use of a hydroperoxide as defined in any one of claims 1 to 4 in the preparation of a dermatological or hair-care composition for the treatment of acne or seborrhoea.
6. Use according to claim 5 wherein the hydroperoxide is used at a concentration of from 0.01 to 20% by weight relative to the total weight of the composition.

z -4
7. Use according to claim 6 wherein the hydroperoxide is used at a concentration of from 0.05 to 10% by weight relative to the total weight of the composition.
8. An anti-acne or anti-seborrhoea composition which comprises, in a carrier, diluent or adjuvant, at least one hydroperoxide as defined in any one of claims 1 to 4.
9. An anti-acne composition according to claim 8, in the form of an ointment, a gel, an emulsion, a lotion or a stick.
10. An anti-seborrhoea Composition according to claim 8, which is in the form of a shampoo or a lotion.
11. A composition according to claim 10 which includes from 3 to 50% by weight of at least one surfactant which is anionic, cationic, nonionic or amphoteric.
12. A composition according to claim 11 which includes from 5 to 25% by weight of at least one surfactant which is anionic, cationic, nonionic or amphoteric. 20
13. An anti-acne or anti- seborrhoea composition according to claim 8 and substantially as hereinbefore described in any one of Composition Examples 1 to 9.
14. A method of cosmetic treatment of acne or seborrhoea which comprises applying to the skin or hair a hydroperoxide of formula (1) as defined in claim 1.

Pub'IShed 1988 Et Tne Paten- Office. SFe HC_FC 6e Lo-con V"C"F 4TF ccpeve Sales Branch, S,. Ma-y Cray, Orpington. Kent BR5 3RD Print-ed by M,-, Itiplex techmques Itd, S,-Ma-7 Cray. Hen. Con 1-87-1