AU2005200539B2

AU2005200539B2 - s-triazine derivatives possessing at least 2 silanic para-aminobenzalmalonate groups; photoprotective cosmetic compositions comprising these derivatives; uses of said s-triazine derivatives

Info

Publication number: AU2005200539B2
Application number: AU2005200539A
Authority: AU
Inventors: Herve Richard
Original assignee: LOreal SA
Current assignee: LOreal SA
Priority date: 2004-02-24
Filing date: 2005-02-08
Publication date: 2007-06-14
Anticipated expiration: 2025-02-08
Also published as: EP1568700B1; DE602005001872T2; CA2497455A1; EP1568700A1; JP4364140B2; KR20060043156A; FR2866648A1; KR100638537B1; CA2497455C; ES2292082T3; BRPI0500552B1; BRPI0500552A; JP2005239722A; DE602005001872D1; AU2005200539A1; FR2866648B1; ATE369373T1

Abstract

Silanic para-aminobenzalmalonate substituted S-triazine compounds (I) are new. Silanic para-aminobenzalmalonate substituted S-triazine compounds of formula (I) are new. R 1-R 3optionally saturated 1-10C alkyl (optionally substituted with one or more halo), phenyl or CH 3; p : 0-1; A : H, optionally saturated 1-8C alkyl, phenyl or Si(CH 3) 3, provided that when A is Si(CH 3) 3, then p is 0; W 1optionally saturated 1-8C alkylene (optionally substituted by hydroxyl group); Z : (C=O)OR 4, -(C=O)R 5, -(C=O)NR 6R 7, -SO 2R 8, CN or (C=O)YCHA(W 1) pSiR 1R 2R 3; R 4H or an optionally saturated 1-20C alkyl radical; R 5, R 81-20C alkyl or 6-12C aryl; R 6, R 7H or 1-20C alkyl; Y : O or NR 7; and B 1chromophoric group of para-aminobenzalmalonate, aminobenzimidazole, benzimidazole, aminobenzoate, aminosalicylate, anthranilate, aminobenzylidenecamphor, aminobenzotriazole, aminobenzoxazole or para aminophenylbenzoxazole substituents, provided that B 1can also be 1-20C aminoalkyl or 6-20C aryl radical which can be optionally substituted by alkyl, hydroxyl and/or alkoxy. Independent claims are also included for: (1) a topically applicable UV-photoprotective cosmetic/dermatological composition (A) comprising (I) and a cosmetic/dermatological vehicle; (2) a regime or regimen for the UV-photoprotection of the skin against the damaging effects of UV-radiation and for controlling the variation in the color of the skin due to UV-radiation comprising topically applying (A); and (3) a synthetic polymer or glass comprising a photostabilizing amount of (I). [Image] ACTIVITY : Dermatological. MECHANISM OF ACTION : None given.

Description

AUSTRALIA

Patents Act 1990 COMPLETE SPECIFICATION STANDARD PATENT Applicant:

L'OREAL

Invention Title: S-TRIAZINE DERIVATIVES POSSESSING AT LEAST 2 SILANIC PARA-AMINOBENZALMALONATE GROUPS; PHOTOPROTECTIVE COSMETIC COMPOSITIONS COMPRISING THESE DERIVATIVES; USES OF SAID S-TRIAZINE DERIVATIVES The following statement is a full description of this invention, including the best method of performing it known to us: 2 (i s-Triazine derivatives possessing at least 2 silanic Spara-aminobenzalmalonate groups; photoprotective 00 0 cosmetic compositions comprising these derivatives; uses of said s-triazine derivatives The invention relates to novel s-triazine In Sderivatives possessing at least 2 specific

(N

i para-aminobenzalmalonate groups and to their uses in Scosmetics.

(N

The invention also relates to photoprotective compositions comprising s-triazine derivatives possessing at least 2 grafted para-aminobenzalmalonate groups as sunscreens active in the UV radiation region.

It is known that radiation with wavelengths of between 280 nm and 400 nm makes possible browning of the human epidermis and that radiation with wavelengths of between 280 and 320 nm, known under the name of UV-B radiation, causes erythemas and skin burns which may be harmful to the development of natural tanning.

It is also known that UV-A rays, with wavelengths of between 320 and 400 nm, which cause browning of the skin, are capable of bringing about a detrimental change in the latter, in particular in the case of sensitive skin and/or of skin continually exposed to solar radiation. UV-A rays bring about in particular a loss of elasticity of the skin and the appearance of wrinkles, resulting in premature H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 1 1 3 cutaneous ageing. They promote the triggering of the Serythemal reaction or accentuate this reaction in some 00 0 subjects and can even be the cause of phototoxic or photoallergic reactions. Thus, for aesthetic and c 5 cosmetic reasons, such as the retention of the natural In elasticity of the skin, people increasingly desire to qi control the effect of UV-A radiation on their skin. The Sterm "sun protection factor" is understood to mean the ratio of the irradiation time necessary to reach the erythemogenic threshold in the presence of the screening agent tested to the irradiation time necessary to reach the same threshold in the absence of screening agent.

It is therefore desirable to have available compounds capable of absorbing UV-A rays.

In addition to their power in screening out UV-A radiation, the desired photoprotective compounds must also exhibit good cosmetic properties, good solubility in conventional solvents and in particular in fatty substances, such as oils and fats, and also good resistance to water and to sweat (persistence) and a satisfactory photostability.

Mention may in particular be made, among all the compounds which have been recommended for this purpose, of the s-triazine derivatives carrying benzalmalonate substituents disclosed in Application H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 4 EP 0 507 691 of the Applicant Company. However, these I compounds possess a liposolubility and photochemical

OO

0 stability which are not yet entirely satisfactory.

The Applicant Company has discovered, surprisingly, a new family of s-triazine derivatives Scarrying at least 2 silanic para-aminobenzalmalonate in groups having good absorbent properties in the long 0 UV-A rays range and exhibiting a solubility in fatty substances, a photostability and cosmetic qualities which are markedly improved with respect to the s-triazine derivatives grafted by benzalmalonates of the prior art mentioned above.

The invention relates to a new family of s-triazine derivatives carrying at least 2 specific para-aminobenzalmalonate groups of formula which will be defined later in detail.

The invention also relates to a cosmetic or dermatological composition, intended for the photoprotection of keratinous substances, comprising, in a cosmetically acceptable medium, at least one compound of formula Other subject-matters will become apparent in the light of the description.

The compounds in accordance with the present invention correspond to the following general formula H:\Angies\keep\Speci\55321 A0106699.DOC 8/02/05 00 o YCH in which: the R 1

R

2 and R 3 radicals, which are identical or different, represent a saturated or unsaturated and linear or branched Cj-Cjo alkyl radical which can comprise one or more halogen atoms (for example Cl, Br or a phenyl radical, p is equal to 0 or 1, -N A denotes hydrogen; a saturated or unsaturated and linear or branched C 1

-C

8 alkyl radical; a phenyl radical; the Si(CH 3 3 group, with the proviso that, when

(I)

in which: A is Si(CH 3 3 then p 0 and R, R 2 and R are methyidentical or W differen a saturated or unsaturated and linear or linear or branched C--CC alkylene radical whihoptionally substituted comprise one or more halogen atoms (for example Cl, Br or Fby a hydroxphenyl radical, 0- p is equal to 0 oR, -S 2 R, -CN A denotes hydrogen; a saturated or unsaturated and linear or branched Ci-C8 alkyl radical; a phenyl radical; the Si(CH3)3 group, with the proviso that, when A is Si(CH3)3, then p 0 and Ri, R2 and R3 are methyl, W is a saturated or unsaturated and linear or branched Ci-C8 alkylene radical optionally substituted by a hydroxyl radical, Z denotes -(C=O)OR4, -(C=O)NR6R7, -SO2Ra, -CN H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 6 or -(C=0)YCHA(W)pSiRiR 2

R

3 I the R 4 radical denotes hydrogen; a saturated or 00 unsaturated and linear or branched Ci-C20 alkyl radical, the R5 radical denotes a linear or branched, C 5 optionally cyclic, Ci-C20 alkyl radical; a C6-C12 aryl, S- the R 6 and R 7 radicals, which are identical or

(N

l~ different, represent hydrogen; a linear or branched C1-C20 alkyl, Y denotes or -NR 7 the R 8 radical denotes a linear or branched alkyl radical; a C6-C12 aryl,

B

1 denotes a chromophoric group chosen from those of the para-aminobenzalmalonate, aminobenzimidazole, benzimidazole, aminobenzoate, aminosalicylate, anthranilate, aminobenzylidenecamphor, aminobenzotriazole, aminobenzoxazole or para-aminophenylbenzoxazole type;

B

1 can also denote a linear or branched aminoalkyl group; a C6-C20 aryl group which is unsubstituted or substituted by alkyl, hydroxyl and alkoxy radicals.

Although only the isomers in which the Z substituent is in the cis position with respect to the substituent with the aromatic ring are represented in the above formula this formula should be understood as also encompassing the corresponding trans H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 7 isomers.

I In the above formula the alkyl radicals 00 can be saturated or unsaturated and linear or branched and chosen in particular from the methyl, ethyl, CM 5 n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-amyl, isoamyl, neopentyl, n-hexyl, n-heptyl, n-octyl, ln 2-ethylhexyl and tert-octyl radicals. The alkyl radical O which is particularly preferred is the methyl radical.

In the above formula the alkoxy radicals are saturated or unsaturated and linear or branched and preferably chosen from the methoxy, ethoxy, n-propyloxy and n-butyloxy radicals.

In the above formula the aryl radicals are preferably phenyl radicals.

According to a specific form of the invention, the compounds of formula can comprise 3 silanic para-aminobenzalmalonate groups, namely that

B

1 denotes a group of following formula (II): HN R 2 ()R2 A R 3 Jl .CH

Y

0 in which Z, A, p, W, RI, R 2 and R 3 have the same meanings indicated above.

H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 88 The compounds of formula preferably I exhibit at least one and more preferably still all of

OO

0 the following characteristics: Z -(C=O)OR 5 -CN or (C=O)YCHA(W) pSiR 2

R

3

R

4 (C 5 Rs is methyl or ethyl, S- A is H, i R 2 to R 4 denote Ci-C4 alkyl and more preferably methyl, S- n is 0, p is 0 or 1, W is a Ci-C2 alkylene radical.

Mention will be made, among the compounds of formula which are more particularly preferred, of those chosen from the compounds of following formulae to H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 0 0I 00 Ny Ai r 0c N0 0 0

C)

0 N N "Hr(2 H:\Angies\keep\speci\P55321 A0106699.DOC 8/02/05 00 00 Il 0T pN >O0(3 oe

I

o 0 ~0 0

N

0 HN YN "r NH (4) NH NH 0 000 N Y N 0 0:J2NH 0 0 H:\Angies\keep\Speci\P55321 AO1O6699.DOC 8/02/05

NH

The compounds of formula can be obtained according to the following scheme XyX

A

o ,CH(W)-S, 3R

NH

2 (I) 3 HX x YN rX 2

(I)

2HX Scheme (a) H:\Angies\keep\Speci\P55321 A0106699.OOC 8/02/05 D 12 in which R 1

R

2

R

3 A, BI, Y, W, Z and p have the

D

_4 definitions of the formula above and X represents a 00 0 halogen, in particular chlorine or bromine.

The above reactions can optionally be carried out in the presence of a solvent (for example: toluene, xylene or acetone/water), at a temperature of between (N 0°C and 250°C, more particularly between 50C and 1500C.

SThe compounds of formula (III) can be prepared according to known methods disclosed, for example, in Application EP 0 507 691 of the Applicant Company.

In the case where Y is the compounds of the formula can also be obtained by transesterification of derivatives of formula (IV) according to the following scheme z O A excess 0

R

PI HO-CH-(W),-Si' 1 S'R R9OH HN ,N NH R3 N

N

RoO JNH 0,

(V)

z, OR,

(IV)

in which R 1

R

2

R

3 A, W, Z and p have the definitions of the formula above and R 9 is methyl or ethyl.

The compounds of formula are generally H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 13 present in the composition of the invention in proportions of between 0.01% and 20% by weight, 00 0 preferably between 0.1% and 10% by weight, with respect to the total weight of the composition.

S 5 Furthermore, the compositions in accordance O with the invention can comprise other additional

(N

in organic or inorganic UV screening agents active in the 0 UV-A and/or UV-B region which are water-soluble or fat-soluble or else insoluble in the cosmetic solvents commonly used.

The additional organic screening agents are chosen in particular from anthranilates; cinnamic derivatives; dibenzoylmethane derivatives; salicylic derivatives; camphor derivatives; triazine derivatives other than those of the invention, such as those disclosed in Patent Applications US 4 367 390, EP 863 145, EP 517 104, EP 570 838, EP 796 851, EP 775 698, EP 878 469, EP 933 376, EP 507 691, EP 507 692, EP 790 243 and EP 944 624; benzophenone derivatives; P,P-diphenylacrylate derivatives; benzotriazole derivatives; benzalmalonate derivatives; benzimidazole derivatives; imidazolines; bisbenzoazolyl derivatives, as disclosed in Patents EP 669 323 and US 2 463 264; p-aminobenzoic acid (PABA) derivatives; methylenebis(hydroxyphenylbenzotriazole) derivatives, as disclosed in Applications US 5 237 071, H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 14 US 5 166 355, GB 2 303 549, DE 197 26 184 and EP I 893 119; benzoxazole derivatives, as disclosed in 00 0 Patent Applications EP 0 832 642, EP 1 027 883, EP 1 300 137 and DE 10162844; screening polymers and screening silicones, such as those disclosed in In Sparticular in Application WO 93/04665; dimers derived

(<N

in from a-alkylstyrene, such as those disclosed in Patent 0 Application DE 19855649; 4,4-diarylbutadienes, as disclosed in Applications EP 0 967 200, DE 19746654, DE 19755649, EP-A-1 008 586, EP 1 133 980 and EP 133 981; and their mixtures.

Mention may be made, as examples of additional organic screening agents, of those denoted below under their INCI names: para-Aminobenzoic acid derivatives:

PABA,

Ethyl PABA, Ethyl Dihydroxypropyl PABA, Ethylhexyl Dimethyl PABA, sold in particular under the name "Escalol 507" by ISP, Glyceryl PABA, PABA, sold under the name "Uvinul P25" by BASF, Salicylic derivatives: Homosalate, sold under the name "Eusolex HMS" by Rona/EM Industries, Ethylhexyl Salicylate, sold under the name "Neo H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 D Heliopan OS" by Haarmann and Reimer, CT Dipropyleneglycol Salicylate, sold under the name 00 0 "Dipsal" by Scher, TEA Salicylate, sold under the name "Neo Heliopan TS" 0 5 by Haarmann and Reimer, In SDibenzoylmethane derivatives:

(<N

i Butyl Methoxydibenzoylmethane, sold in particular under 0 the trade name "Parsol 1789" by Hoffmann-LaRoche, Isopropyl Dibenzoylmethane, Cinnamic derivatives: Ethylhexyl Methoxycinnamate, sold in particular under the trade name "Parsol MCX" by Hoffmann-LaRoche, Isopropyl Methoxycinnamate, Isoamyl Methoxycinnamate, sold under the trade name "Neo Heliopan E 1000" by Haarmann and Reimer, Cinoxate, DEA Methoxycinnamate, Diisopropyl Methyl Cinnamate, Glyceryl Ethylhexanoate Dimethoxycinnamate, P,P-Diphenylacrylate derivatives: Octocrylene, sold in particular under the trade name "Uvinul N539" by BASF, Etocrylene, sold in particular under the trade name "Uvinul N35" by BASF, Benzophenone derivatives: Benzophenone-1, sold under the trade name "Uvinul 400" by BASF, H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 16 D Benzophenone-2, sold under the trade name "Uvinul ^4 by BASF, 00 0 Benzophenone-3 or Oxybenzone, sold under the trade name "Uvinul M40" by BASF, Cr 5 Benzophenone-4, sold under the trade name "Uvinul by BASF, l O Benzophenone-6, sold under the trade name "Helisorb 11" by Norquay, Benzophenone-8, sold under the trade name "Spectra-Sorb UV-24" by American Cyanamid, Benzophenone-9, sold under the trade name "Uvinul DS- 49" by BASF, Benzophenone-12, n-Hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate, Benzylidenecamphor derivatives: 3-Benzylidene camphor, manufactured under the name "Mexoryl SD" by Chimex, 4-Methylbenzylidene camphor, sold under the name "Eusolex 6300" by Merck, Benzylidene Camphor Sulfonic Acid, manufactured under the name "Mexoryl SL" by Chimex, Camphor Benzalkonium Methosulfate, manufactured under the name "Mexoryl SO" by Chimex, Terephthalylidene Dicamphor Sulfonic Acid, manufactured under the name "Mexoryl SX" by Chimex, H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 17 D Polyacrylamidomethyl Benzylidene Camphor, manufactured under the name "Mexoryl SW" by Chimex, 00 0 Phenylbenzimidazole derivatives: Phenylbenzimidazole Sulfonic Acid, sold in particular under the trade name "Eusolex 232" by Merck, SDisodium Phenyl Dibenzimidazole Tetrasulfonate, sold

(N

ln under the trade name "Neo Heliopan AP" by Haarmann and SReimer, Triazine derivatives: Anisotriazine, sold under the trade name "Tinosorb S" by Ciba-Geigy, Ethylhexyl triazone, sold in particular under the trade name "Uvinul T150" by BASF, Diethylhexyl Butamido Triazone, sold under the trade name "Uvasorb HEB" by Sigma 3V, Phenylbenzotriazole derivatives: Drometrizole Trisiloxane, sold under the name "Silatrizole" by Rhodia Chimie, Methylene Bis-Benzotriazolyl Tetramethylbutylphenol, sold in the solid form under the trade name "Mixxim BB/100" by Fairmount Chemical or in the micronized form in aqueous dispersion under the trade name "Tinosorb M" by Ciba Specialty Chemicals, Anthranilic derivatives: Menthyl anthranilate, sold under the trade name "Neo Heliopan MA" by Haarmann and Reimer, H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 18 Imidazoline derivatives: Ethyihexyl Dimethoxybenzylidene Dioxoimidazoline 00 Propionate, Benzalmalonate derivatives: M 5 Polyorganosiloxanes with benzalmalonate functional groups, such as Polysilicone-15, sold under the trade name "Parsol SLX" by Hoffmann-LaRoche, 4, 4-Diarylbutadiene derivatives: 1, 1-Dicarboxy -dimethyipropyl) 4diphenylbutadiene, Benzoxazole derivatives: 2, 4-Bis [5-1 (dimethylpropyl) benzoxazol-2-yl- (4-phenyl) imino]-6-(2-ethylhexyl)imino-1,3,5-triazine, sold under the name Uvasorb K2A by Sigma 3V; and their mixtures.

The preferred additional organic UV screening agents are chosen from: Ethylhexyl Salicylate, Ethylhexyl Methoxycinnamate, Butyl Methoxydibenzoylmethane, Octocrylene, Phenylbenzimidazole Sulfonic Acid, Ben zophenone-3, Ben zophenone-4, n-Hexyl 2- (4-diethylamino-2-hydroxybenzoyl)benzoate, H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 19 4-Methylbenzylidene camphor, STerephthalylidene Dicamphor Sulfonic Acid, 00 0 Disodium Phenyl Dibenzimidazole Tetrasulfonate, Anisotriazine, Ethylhexyl triazone, Diethylhexyl Butamido Triazone, V3 Methylene Bis-benzotriazolyl Tetramethylbutylphenol, SDrometrizole Trisiloxane, l,l-Dicarboxy(2,2'-dimethylpropyl)-4,4diphenylbutadiene, 2,4-Bis[5-1(dimethylpropyl)benzoxazol-2-yl-(4-phenyl)imino]-6-(2-ethylhexyl)imino-1,3,5-triazine, and their mixtures.

The additional inorganic screening agents are chosen from pigments or alternatively nanopigments (mean size of the primary particles: generally between nm and 100 nm, preferably between 10 nm and 50 nm) formed of coated or uncoated metal oxides, such as, for example, nanopigments formed of titanium oxide (amorphous or crystalline in the rutile and/or anatase form), iron oxide, zinc oxide, zirconium oxide or cerium oxide, which are all UV photoprotective agents well known per se. Conventional coating agents are furthermore alumina and/or aluminium stearate. Such nanopigments formed of coated or uncoated metal oxides H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 e are disclosed in particular in Patent Applications EP p 518 772 and EP 518 773.

00 The additional UV screening agents in accordance with the invention are generally present in C 5 the compositions according to the invention in Sproportions ranging from 0.01 to 20% by weight with

(N

l~ respect to the total weight of the composition and O preferably ranging from 0.1 to 10% by weight with respect to the total weight of the composition.

The cosmetic compositions according to the invention can additionally comprise agents for the artificial tanning and/or browning of the skin (selftanning agents), such as dihydroxyacetone (DHA).

The compositions in accordance with the present invention can additionally comprise conventional cosmetic adjuvants chosen in particular from fatty substances, organic solvents, ionic or nonionic thickeners, softening agents, humectants, antioxidants, moisturizing agents, desquamating agents, agents for combating free radicals, agents for combating pollution, antibacterials, antiinflammatories, depigmenting agents, propigmenting agents, opacifiers, stabilizing agents, emollients, silicones, antifoaming agents, insect repellants, fragrances, preservatives, anionic, cationic, nonionic, zwitterionic or amphoteric surfactants, substance P H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 21 D antagonists, substance CGRP antagonists, fillers, 4 pigments, polymers, propellants, basifying or 00 acidifying agents, or any other ingredient commonly used in the cosmetics and/or dermatological field.

C 5 The fatty substances can be composed of an O oil or a wax or their mixtures. The term "oil" is

(N

ln understood to mean a compound which is liquid at O ambient temperature. The term "wax" is understood to mean a compound which is solid or substantially solid at ambient temperature and which has a melting point generally of greater than 350C.

Mention may in particular be made, among the oils which can participate in the composition of the fatty phase, of: mineral oils, such as liquid paraffin and liquid petrolatum, oils of animal origin, such as perhydrosqualene, oils of vegetable origin, such as sweet almond oil, avocado oil, castor oil, olive oil, jojoba oil, sesame oil, groundnut oil, grape seed oil, rapeseed oil, coconut oil, hazelnut oil, karite butter, palm oil, apricot kernel oil, calophyllum oil, rice bran oil, maize germ oil, wheat germ oil, soybean oil, sunflower oil, evening primrose oil, safflower oil, passionflower oil and rye oil, H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 22 D synthetic oils, such as purcellin oil, [I esters, such as, for example, butyl myristate, 00 O isopropyl myristate, cetyl myristate, isopropyl palmitate, isopropyl adipate, ethylhexyl adipate, butyl C 5 stearate, hexadecyl stearate, isopropyl stearate, octyl stearate, isocetyl stearate, decyl oleate, hexyl l laurate, propylene glycol dicaprylate and esters Sderived from lanolic acid, such as isopropyl lanolate or isocetyl lanolate, isoparaffins and poly-a-olefins.

Mention may also be made, as other oils which can be used in the compositions according to the invention, of benzoates of C 12

-C

15 fatty alcohols (Finsolv TN from Finetex), ethers, lipophilic derivatives of amino acids, such as isopropyl Nlauroylsarcosinate (Eldew SL-205 from Ajinomoto), fatty alcohols, such as lauryl alcohol, cetyl alcohol, myristyl alcohol, stearyl alcohol, palmityl alcohol, oleyl alcohol and 2-octyldodecanol, acetylglycerides, octanoates and decanoates of alcohols and of polyalcohols, such as those of glycol and of glycerol, ricinoleates of alcohols and of polyalcohols, such as those of cetyl, fatty acid triglycerides, such as caprylic/capric triglycerides or triglycerides of saturated Cio-C 18 fatty acids, fluorinated and perfluorinated oils, lanolin, hydrogenated lanolin, acetylated lanolin and, finally, volatile or non- H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 D 23 volatile silicone oils.

SOf course, the fatty phase can also comprise 0 one or more conventional lipophilic cosmetic adjuvants, such as, for example, waxes, lipophilic gelling agents, surfactants or organic or inorganic particles, and in In O particular those which are already commonly used in the manufacture and the production of antisun cosmetic Scompositions.

(N

Mention may be made, as waxy compounds, of paraffin wax, carnauba wax, beeswax or hydrogenated castor oil.

Mention may be made, among organic solvents, of lower alcohols and polyols. The latter can be chosen from glycols and glycol ethers, such as ethylene glycol, propylene glycol, butylene glycol, dipropylene glycol or diethylene glycol.

The thickeners can be chosen in particular from crosslinked acrylic polymers, such as the Carbomers, crosslinked acrylate/C 10

-C

30 alkyl acrylate polymers of the Pemulen type or polyacrylate-3, sold under the name Viscophobe DB 1000 by Amerchol; polyacrylamides, such as the polyacrylamide, C 13

-C

14 isoparaffin and laureth-7 emulsion sold under the name Sepigel 305 by Seppic, AMPS homopolymers or copolymers, such as Hostacerin AMPS sold by Clariant, modified or unmodified guar and cellulose gums, such as hydroxy- H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 24 3D propylated guar gum, methylhydroxyethylcellulose and Shydroxypropylmethylcellulose, xanthan gum or nanometric 00 0 silicas of Aerosil type.

Of course, a person skilled in the art will take care to choose the optional additional compound or Scompounds mentioned above and/or their amounts so that

(N

V the advantageous properties intrinsically attached to C the compounds in accordance with the invention are not, or not substantially, detrimentally affected by the envisaged addition or additions.

The compositions according to the invention can be prepared according to the techniques well known to a person skilled in the art, in particular those intended for the preparation of emulsions of oil-inwater or water-in-oil type.

This composition can be provided in particular in the form of a simple or complex emulsion W/O, O/W/O or such as a cream or a milk, or in the form of a gel or of a cream gel, in the form of a lotion, of an oil, of a powder or of a solid stick and can optionally be packaged as an aerosol and provided in the form of a foam or spray.

Preferably, the compositions according to the invention are provided in the form of an oil-in-water or water-in-oil emulsion.

When it is a question of an emulsion, the H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 e aqueous phase of the latter can comprise a nonionic 4 vesicular dispersion prepared according to known 00 processes (Bangham, Standish and Watkins, J. Mol.

Biol., 13, 238 (1965), FR 2 315 991 and FR 2 416 008).

5 When the cosmetic composition according to In the invention is used for caring for the human Sepidermis, it can be provided in the form of a Ssuspension or dispersion in solvents or fatty substances, in the form of a nonionic vesicular dispersion or in the form of an emulsion, preferably of oil-in-water type, such as a cream or a milk, or in the form of an ointment, gel, cream gel, suntan oil, solid stick, powder, aerosol foam or spray.

When the cosmetic composition according to the invention is used for caring for the hair, it can be provided in the form of a shampoo, lotion, gel, emulsion or nonionic vesicular dispersion and can constitute, for example, a rinse-out composition, to be applied before or after shampooing, before or after dyeing or bleaching, and before, during or after perming or hair straightening, a styling or treating lotion or a styling or treating gel, a lotion or a gel for blow drying or hair setting, or a composition for perming or straightening, dyeing or bleaching the hair.

When the composition is used as a product for making up the nails, lips, eyelashes, eyebrows or skin, H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 26 such as a treatment cream for the epidermis, Sfoundation, lipstick tube, eye shadow, face powder, 00 mascara or eyeliner, it can be provided in the anhydrous or aqueous, pasty or solid form, such as oilin-water or water-in-oil emulsions, nonionic vesicular In O dispersions, or suspensions.

SBy way of indication, for the antisun formulations in accordance with the invention which

(N

exhibit a vehicle of oil-in-water emulsion type, the aqueous phase (comprising in particular the hydrophilic screening agents) generally represents from 50 to by weight, preferably from 70 to 90% by weight, with respect to the entire formulation, the oily phase (comprising in particular the lipophilic screening agents) from 5 to 50% by weight, preferably from 10 to by weight, with respect to the entire formulation, and the (co)emulsifier(s) from 0.5 to 20% by weight, preferably from 2 to 10% by weight, with respect to the entire formulation.

The compositions according to the invention can be provided in the form of vaporizable fluid lotions in accordance with the invention and can be applied to the skin or hair in the form of fine particles by means of pressurization devices. The devices in accordance with the invention are well known to a person skilled in the art and comprise non-aerosol H:\Angies\keep\Speci\P55321 A0106699DOC 8/02/05 27 D pumps or "atomizers", aerosol containers comprising a i propellant, and aerosol pumps using compressed air as 00 0 propellant. The latter are disclosed in Patents US 4 077 441 and US 4 850 517 (forming an integral part of M 5 the content of the description).

The compositions packaged as an aerosol in

(N

V) accordance with the invention generally comprise Sconventional propellants, such as, for example, hydrofluoro compounds, dichlorodifluoromethane, difluoroethane, dimethyl ether, isobutane, n-butane, propane or trichlorofluoromethane. They are preferably present in amounts ranging from 15 to 50% by weight with respect to the total weight of the composition.

Another subject-matter of the invention is the use of a compound of formula as defined above in a cosmetic or dermatological composition as agent for screening out UV radiation.

Another subject-matter of the invention is the use of a compound of formula as defined above in a cosmetic composition as agent for controlling the variation in the colour of the skin due to UV radiation.

Another subject-matter of the invention is the use of a compound of formula as defined above as photostabilizing agent for synthetic polymers, such as plastics, or for glasses, in particular spectacle H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 28

(N

D glasses or contact lenses.

SConcrete but in no way limiting examples 00 0 illustrating the invention will now be given.

EXAMPLE 1: Preparation of 2,4,6-tris(di(trimethylsilyl- S 5 methyl) 4'-aminobenzalmalonate)-s-triazine: 00 0 H1 NO HN N NH SI

N-N

0 0 NH 0 0 -II 0 o 0 0 0 Si First stage: Preparation of di(trimethylsilylmethyl) malonate: Malonic acid (8.3 g, 0.079 mol) and trimethylsilylmethyl alcohol (18.35 g, 0.176 mol) in ml of toluene in the presence of 0.1 ml of concentrated sulphuric acid are brought to reflux for 3 hours in a reactor surmounted by a Dean and Stark apparatus. The water formed is removed by azeotropic distillation. The organic phase is washed 3 times with water and is dried over sodium sulphate. After filtering and evaporating the solvent under vacuum, 22 g of a colourless oil are obtained. After H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 29 distillation under a vacuum of 0.15 mbar, the 9 di(trimethylsilylmethyl) malonate fractions distilling 00 0 at 74-76 C are collected (19.6 g, Yield 90%) in the form of a colourless oil used as is in the following C( 5 stage.

In 8 Second stage: Preparation of di(trimethylsilylmethyl) i~ 4-nitrobenzalmalonate: 0 p-Nitrobenzaldehyde (4.65 g, 0.03 mol) and di(trimethylsilylmethyl) malonate (8.5 g, 0.031 mol) are placed in 15 ml of toluene in a round-bottomed flask equipped with a Dean and Stark apparatus surmounted by a reflux condenser and sparged with nitrogen. The catalyst prepared in advance, acetic acid (0.2 ml) and piperidine (0.3 ml) in suspension in 0.5 ml of toluene, is added thereto. The mixture is brought to reflux for 5 hours with stirring and the water formed is removed via the Dean and Stark apparatus. Two further additions of the same amount of catalyst were necessary. The toluene is removed under vacuum and the residue is taken up in isopropyl ether and then washed twice with water. After drying the organic phase and evaporating the solvent, a red-brown oil is obtained. After purifying on a silica column (eluent: heptane/AcOEt 7.1 g (Yield 57%) of clean di(trimethylsilylmethyl) 4-nitrobenzalmalonate fractions are collected in the form of a pale yellow H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 solid used as is in the following stage.

-I Third stage: Preparation of di(trimethylsilylmethyl) 00 0 4-aminobenzalmalonate: The derivative from the preceding stage c 5 (3.2 g, 0.0078 mol) is dispersed in 5.5 ml of acetic O acid with stirring and while sparging with nitrogen.

i 8 ml of water are added thereto. The mixture is heated 0 to 500C. Iron (4.36 g) is added thereto portionwise without exceeding a temperature of 55 0 C (introduction time 1 hour). Subsequently, acetic acid (8 ml) is added dropwise without exceeding a temperature of 550C (introduction time 1 hour). Heating is carried out for an additional 45 minutes at 55 0 C. The mixture is cooled, dichloromethane is added and the mixture is filtered through celite. The organic phase is washed with water, with a saturated sodium bicarbonate solution and with water and is then dried over sodium sulphate. After concentrating under reduced pressure, an orange-coloured oil is obtained and is purified by chromatography on a silica column (eluent: heptane/AcOEt 1.8 g (Yield 62%) of clean di(trimethylsilylmethyl) 4-aminobenzalmalonate fractions are collected in the form of a yellow solid used as is in the following stage.

Fourth stage: Preparation of the derivative of Example 1: H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 31 The preceding derivative (1.1 g, 9.66 x [I 10 4 mol), dissolved in 5 ml of toluene, is introduced 00 0 dropwise at 0-5 0 C into a dispersion of cyanuric chloride (0.18 g, 3.22 x 10-4 mol) in 10 ml of toluene M 5 while sparging with nitrogen. The mixture is Ssubsequently heated at reflux for 5 hours while

(N

ln degassing with nitrogen. After cooling, the organic 0 phase is washed with water and then with an aqueous sodium bicarbonate solution. The organic phase is concentrated under reduced pressure. The residue obtained is dissolved in 1,2-dichloroethane. The organic phase is washed with water, with a saturated sodium bicarbonate solution and with water and is then dried over sodium sulphate. After concentrating under reduced pressure, a yellow oil is obtained and is purified by chromatography on a silica column (eluent: heptane/AcOEt 85/15). 0.75 g (Yield 64%) of clean fractions of the derivative of Example 1 is collected in the form of a pale yellow gum: UV (ethanol) Xmax 355 nm; emax 118 970; El% 987.

H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 D 32 EXAMPLE 2: Preparation of 2,4,6-tris(di(trimethylsilylethyl) 4'-aminobenzalmalonate)-s-triazine: 00 o 0 HN N NH 0O 0 NH 0 0 N 0 2,4,6-Tris(diethyl 4'-aminobenzalmalonate)-striazine (1 g, 1.16 x 10 4 mol) (Example 1 of Application EP) is dissolved in 5 ml of trimethylsilylethyl alcohol while sparging with nitrogen. The mixture is subsequently heated at reflux for 25 hours with 0.2 g of para-toluenesulphonic acid. After addition of 30 ml of dichloromethane, the organic phase is washed with water and then with an aqueous sodium bicarbonate solution, and dried. It is concentrated under reduced pressure. The residue obtained is purified by chromatography on a silica column (eluent: heptane/AcOEt 85/15). 0.35 g (Yield 32%) of the derivative of Example 2 is collected in the form of a pale yellow gum: UV (ethanol) kmax 355 nm; Emax 125 250; El% 965.

H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 in D 33 EXAMPLE 3: Preparation of 2,4-bis(di(trimethylsilylmethyl) 4'-aminobenzalmalonate)-6-(para-methoxyphenyl)- 00 0 s-triazine: O N N H in ,of 0 )NH r 0 0 0 y 1 I i Io 0 0 2,4-Dichloro-6-(para-methoxyphenyl)-striazine (0.67 g, 2.61 x 10 3 mol) is dispersed in 10 ml of toluene. A solution in 10 ml of di(trimethylsilylmethyl) 4-aminobenzalmalonate (2 g, 5.2 x 10 3 mol) is added thereto dropwise while sparging with nitrogen.

The mixture is brought to reflux for 4 hours minutes. After an addition of 20 ml of dichloromethane, the organic phase is washed with water, with a saturated sodium bicarbonate solution and with water and is then dried over sodium sulphate. The organic phase is concentrated under vacuum. The residue is subjected to separation on a silica column (eluent: heptane/EtOAc Clean fractions are recovered in the form of a pale yellow oil which is precipitated from an ethanol/heptane mixture to produce the derivative of Example 3 (1.42 g, Yield 58%) in the form of an amorphous pale yellow powder: UV (ethanol) nmax 351 nm; emax 74 540; EI% 791, H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 C) 34 N 3 40 nm; S~max 74 450; 790, 2ia 9 26 nm; Emax 28 280; 340.

00 EXAMPLE 4: Preparation of 2,4-bis(di(trimethylsilylmethyl) 4' -aminobenzalmalonate) -aminobenzimidazole)-s-triazine: 0S 0 00

N

0 HN Y, N INH NH NH NH 0 0 0 0 First stage: Preparation of 2,4-dichloro-6-(2' -aminobenzimidazole) -s-triazine: Cyanuric chloride (18 g, 0.097 mol) is dissolved at 000 in 150 ml of acetone. 50 ml of water are added thereto. A suspension of 2-aminobenzimidazole (13 g, 0.097 mol) in 100 ml of acetone is added thereto dropwise at 000 while sparging with nitrogen. A solution of sodium carbonate (7 g) in 150 ml of water is added thereto. The heterogeneous mixture is left stirring at 0-5'C for 2 hours. The reaction mixture is filtered. The solid is washed with dichloromethane, with water and with a small amount of acetone. After H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 drying, 25 g (Yield 91%) of 2,4-dichloro-6-(2'-aminobenzimidazole)-s-triazine are recovered in the form of 00 0 a beige powder used as is in the following stage.

Second stage: Preparation of the derivative of C 5 Example 4: o The preceding derivative (0.267 g, 9.5 x I 10-4 mol) is dispersed with di(trimethylsilylmethyl) 0 4-aminobenzalmalonate (0.72 g, 1.9 x 10 3 mol) in 10 ml of toluene. The mixture is brought to reflux for 4 hours 30 minutes. The organic phase is concentrated under vacuum. After an addition of 20 ml of dichloromethane, the organic phase is washed with water, with a saturated sodium bicarbonate solution and with water and is then dried over sodium sulphate.

After crystallization from a dichloromethane/MeOH mixture, the derivative of Example 4 is obtained (0.66 g, Yield 72%) in the form of an amorphous light brown powder: UV (ethanol) kmax 342 nm; shoulder Emax 61 910; EI% 640, kmax 325 nm; Emax 76 420; E 1 790.

H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 36 EXAMPLE OF FORMULATION IN AN ONw EMULSION CHEMICAL NAME Composition COMMERCIAL REFERENCE Supplier (g GLYCERYL MONOSTEARATE/POLYETHYLENE GLYCOL STEARATE (100 EO) MIXTURE 1 SIMULSOL 165 Seppic STEARIC ACID STEARINE TP 1200 PASTILLES St6arinerie Dubois POLYDIMETHYLS ILOXANE 200 FLUID 350 CS Dow Corning CETYL ALCOHOL LANETTE 16 NF Cognis CETYLSTEARYL GLYCOSIDE/CETYLSTEARYL ALCOHOL MIXTURE 2 MONTANOV 68 Seppic PRESERVATIVE 1 TRI ETHANOLAMINE 0. TRIETHANOLAMINE BASF CAPRIC/CAPRYLIC ACID TRIGLYCERIDE MYRITOL 317 Cognis COMPOUND OF EXAMPLE 1 GLYCEROL PRICERINE 9091 Uniquema XANTHAN GUM 0.1 KELTROL T CP Kelco CROSSLINKED ACRYLIC ACID/Cl 0

-C

3 0

ALKYL

ACRYLATE COPOLYMER 0.12 PEMULEN TR-1 Noveon TRIETHANOLAMINE s.p TRIETHANOLAMINE BASF DEMINERALIZED WATER lq.s. for 100 gl H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 37 PHOTOSTABILITIES COMPARED BETWEEN A COMPOUND OF THE SPRIOR ART AND THE COMPOUND ACCORDING TO THE INVENTION 00 0OF EXAMPLE 1 Products tested: m 5 2,4,6-Tris(diisobutyl 4'-aminobenzalmalonate)-so triazine prior art (Example 1 of Patent EP 507 691) V' 2,4,6-Tris(di(trimethylsilylmethyl) 4'-aminobenzal- 0 malonate)-s-triazine Example 1 according to the invention.

The two products were dissolved at 5% by weight in the oil Miglyol 812. Approximately 10 mg of oily solution are spread over 10 cm 2 at the surface of a hollow disc of frosted glass; the amount is determined by weighing.

The films of the oily solutions are irradiated for one hour using an Oriel solar simulator (UV-A 14.2 mW/cm 2 UV-B 0.41 mW/cm 2 then extracted with 10 ml of ethanol comprising 10% of isopropanol and subjected to ultrasound for 5 min. The products are quantified by HPLC of the extracts.

HPLC conditions: column: UP5WOD-25QS, 250 x 4.6 mm, 5 pm, Interchrom; eluent: methanol (Comparative Example 1) and 96% of methanol 4% of water (Example flow rate: 1 ml/min; volume injected: 10 pl; detection: diode array; rt (min): 5.2 (Comparative Example 1) and 13.8 (Example 1).

H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 38 eD The degrees of loss are determined by comparison of the amounts of product present in the 00 0 irradiated samples and in the nonirradiated controls prepared simultaneously and treated in the same way f 5 (means over 3 samples; S surface/mg solution): S% loss 100 X (So Sirr)/So l PHOTOSTABILITY RESULTS C- Compound Test of disappearance Compound (prior art) 1 11 Compound (prior art) 2 Compound (prior art) 3 9 Example 1 4 0 Example 1 5 0 Example 1 6 0 Compound of the prior art: The loss in Miglyol is between 9 and 11% after exposure for one hour to the simulator of a 1 mg/cm 2 film of 5% solution.

Example 1: No loss in Miglyol is observed after exposure for one hour to the simulator of a 1 mg/cm 2 film of 5% solution.

In the claims which follow and in the preceding description of the invention, except where the context requires otherwise due to express language or necessary implication, the word "comprise" or variations such as "comprises" or "comprising" is used in an inclusive sense, i.e. to specify the presence of H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 39 c. the stated features but not to preclude the presence or

D

addition of further features in various embodiments of 00 the invention.

It is to be understood that, if any prior art C 5 publication is referred to herein, such reference does Snot constitute an admission that the publication forms a part of the common general knowledge in the art, in c1 Australia or any other country.

H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05

Claims

2. Compound according to Claim 1, where Bi denotes a group of the following formula (II): H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 42 HN RI W) P R 3 Y CH z 0 in which Z, Y, A, p, W, R 1 R 2 and R 3 have the same meanings indicated in Claim 1.
3. Compound according to Claim 1 or 2, exhibiting at least one of the following characteristics: Z ORS, -CN or YCHA pSiR 2 R 3 R 4 R 5 is methyl or ethyl, A is H, R 2 to R 4 denote Cl-C 4 alkyl and more preferably methyl, n isO0, p is 0 or 1, W is a Cl-C 2 alkylene radical.
4. Compound according to Claim 3, chosen from the following compounds: N.\Melbourne\Cases\Patent\55OOO-55999\P5532I .AU\Specis\P55321.AU Specification 2007-4-S.doc 10/04/07 000 NY 0 0~ ydONH j 0 00 0 SJ .A0 0 YK N NB If (2 N II 0 0N N e J 0 NHN S r H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 I 0 44 0 N N N o "HN Y ""NN N N NH 0 O O 0 Si ,N I HNHN N N NrN S N S0N NH 0< 0 ,SiO X0 0 0 r SI, r r O NH 0 HN N N N N (6) NH O O r 0 NH Cosmetic or dermatological composition intended for the photoprotection of keratinous substances, characterized in that it comprises, in a cosmetically acceptable vehicle, at least one compound H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 45 of formula as defined in any one of Claims 1 to 4.
6. Composition according to Claim characterized in that the compound of formula is present in the composition at a content ranging from 0.01 to 20% or 0.1% to 10% by weight with respect to the total weight of the composition.
7. Composition according to Claim 5 or 6, characterized in that the said cosmetically acceptable vehicle is provided in the form of an emulsion of oil-in- water or water-in-oil type.
8. Composition according to any one of Claims to 7, characterized in that it additionally comprises one or more additional organic or inorganic screening agents active in the UV-A and/or UV-B region.
9. Composition according to Claim 8, characterized in that the said additional organic screening agents are chosen from anthranilates; cinnamic derivatives; dibenzoylmethane derivatives; salicylic derivatives; camphor derivatives; triazine derivatives other than those defined in the preceding claims; benzophenone derivatives; P, -diphenylacrylate derivatives; benzotriazole derivatives; benzalmalonate derivatives other than those defined in the preceding claims; benzimidazole derivatives; imidazolines; bis- N.\Melbourne\Caaea\Patent\55000-55999\P55321.AU\Specis\P55321.AU Specification 2007-4-5.doc 10/04/07 46 benzoazolyl derivatives; benzoxazole derivatives; p-aminobenzoic acid (PABA) derivatives; methylenebis- 00 (hydroxyphenylbenzotriazole) derivatives; benzoxazole derivatives; screening polymers and screening silicones; dimers derived from c-alkylstyrene; 4,4-diarylbutadienes; and their mixtures. tim 10. Composition according to Claim 9, characterized in that the said additional organic screening agents are chosen from: Ethylhexyl Salicylate, Ethylhexyl Methoxycinnamate, Butyl Methoxydibenzoylmethane, Octocrylene, Phenylbenzimidazole Sulfonic Acid, Benzophenone-3, Benzophenone-4, n-Hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate, 4-Methylbenzylidene camphor, Terephthalylidene Dicamphor Sulfonic Acid, Disodium Phenyl Dibenzimidazole Tetrasulfonate, 2,4,6-Tris(diisobutyl 4'-aminobenzalmalonate)-s- triazine, Anisotriazine, Ethylhexyl triazone, Diethylhexyl Butamido Triazone, H:\Angies\keep\Speci\P55321 A0106699.DOC 8/02/05 47 Methylene Bis-benzotriazolyl Tetramethylbutylphenol, Drometrizole Trisiloxane, 1,1-Dicarboxy(2,2'-dimethylpropyl)-4,4-diphenylbutadiene, 2,4-Bis[5-1(dimethylpropyl)benzoxazol-2-yl-(4-phenyl)- imino]-6-(2-ethylhexyl)imino-1,3,5-triazine, and their mixtures.
11. Composition according to Claim characterized in that the additional inorganic screening agents are pigments or nanopigments formed of coated or uncoated metal oxides.
12. Composition according to Claim 11, characterized in that the said pigments or nanopigments are chosen from coated or uncoated titanium oxide, zinc oxide, iron oxide, zirconium oxide, cerium oxide and their mixtures.
13. Composition according to any one of Claims to 12, characterized in that it additionally comprises at least one agent for the artificial tanning and/or browning of the skin.
14. Composition according to any one of Claims to 13, characterized in that it additionally comprises at least one adjuvant chosen from fatty substances, organic solvents, ionic or nonionic thickeners, softening agents, humectants, antioxidants, moisturizing agents, desquamating agents, agents for combating free radicals, N:\Melbourne\Cases\Patent\55000-55999\P55321.AU\Specis\P55321.AU Specification 2007-4-5.doc 10/04/07 48 agents for combating pollution, antibacterials, anti- inflammatories, depigmenting agents, propigmenting agents, opacifiers, stabilizing agents, emollients, silicones, antifoaming agents, insect repellants, fragrances, preservatives, anionic, cationic, nonionic, zwitterionic or amphoteric surfactants, substance P antagonists, substance CGRP antagonists, fillers, pigments, polymers, propellants, or basifying or acidifying agents. Composition according to any one of Claims 5 to 14, characterized in that it is a protective composition for the human epidermis or an antisun composition and that it is provided in the form of a nonionic vesicular dispersion, of an emulsion, in particular of an emulsion of oil-in-water type, of a cream, of a milk, of a gel, of a cream gel, of a suspension, of a dispersion, of an oil, of a powder, of a solid stick, of a foam or of a spray.
16. Composition according to any one of Claims to 14, characterized in that it is a composition for making up the eyelashes, eyebrows, nails or skin and that it is provided in the anhydrous or aqueous, pasty or solid form, or in the form of an emulsion, of a suspension or of a dispersion.
17. Composition according to any one of Claims 5 to 14, characterized in that it is a composition intended for the protection of the hair against N,\Melbourne\Casea\Patent\55000-55999\P55321.AU\Specia\P55321.AU Specification 2007-4-5.doc 10/04/07 49 Sultraviolet rays and that it is provided in the form of a shampoo, of a lotion, of a gel, of an emulsion or of a 00 nonionic vesicular dispersion.
18. Use of a compound of formula as defined lt 5 in any one of Claims 1 to 4 in a cosmetic or O dermatological composition as an agent for screening out UV radiation. C( 19. Use of a compound of formula as defined in any one of Claims 1 to 4 in a cosmetic composition as an agent for controlling the variation in the colour of the skin due to UV radiation. A process for the preparation of a compound of formula as defined in claim 1, comprising the step of: reacting a compound of formula (VI) with a compound of formula (III): N N M (VI) N:\Melbourne\Cases\Patent\55000-55999\P55321.AU\Specis\P55321.AU Specification 2007-4-5.doc 28/05/07 50 R, A R 2 /R 3 CH 0 Y NH 2 1) wherein M represents X or B1, where B 1 has the same meaning indicated in claim 1 and X represents halogen; and Z, Y, A, W, p, R 1 R 2 and R 3 have the same meanings indicated in claim 1; to produce a compound of formula
21. A compound of formula compositions comprising it, uses involving it or a process for its preparation, substantially as herein described with reference to the accompanying examples (excluding comparative examples). N.\Melbourne\Cases\Patent\55000-55999\P55321.AU\Specis\P55321.AU Specification 2007-4-5.doc 10/04/07