BRPI0406835B1 - Triazine Derivatives As UV Absorbers, Process For Their Preparation And Cosmic Preparation Containing The Same - Google Patents

Description

(54) Title: TRIAZINE DERIVATIVES AS UV ABSORBERS, PROCESS FOR ITS PREPARATION AND COSMETIC PREPARATION CONTAINING THE SAME (51) lnt.CI .: C07D 251/18; C07D 251/20 (30) Unionist Priority: 20/01/2003 EP 03 405018.7 (73) Owner (s): CIBA SPECIALTY CHEMICALS HOLDING INC.

(72) Inventor (s): THOMAS EHLIS; DIETMAR HÜGLIN; ELEK BORSOS (85) National Phase Start Date: 20/07/2005

Descriptive Report of the Invention Patent for TRIAZINE DERIVATIVES AS UV ABSORBERS, PROCESS FOR ITS PREPARATION AND COSMETIC PREPARATION CONTAINING THE SAME.

The present invention relates to anisyl-bis (arylamino) -triazines, the preparation of these compounds and their use as UV absorbers in cosmetic and pharmaceutical formulations.

Depending on their wavelength, UV rays are divided into UV-A rays (320-400 nm) and UV-B rays (280-320 nm). The harmful effect, specifically the occurrence of sunburn (erythema), increases not only with the duration of the exposure, but also with the decrease in the wavelength and is thus significantly stronger and more marked in the case of UV-B radiation, which in the case of UV-A radiation. Since erythema can occur even after short exposure to the sun, in some cases, 20-30 minutes, effective protection against this radiation is of particular importance.

Compounds that absorb ultraviolet light (UV absorbers) do not absorb the full spectrum of ultraviolet light to the same degree at each wavelength. Characteristics of UV absorbers are therefore the wavelength at which the absorption is greatest (in nm) and the percentage of absorption at that wavelength (relative, calculated using the Lambert-Beer law). Both the wavelength and percentage of absorption at maximum absorbance can be influenced by other components present in conjunction with the UV absorber.

Anisyl-bis (arylamino) -triazines have now been found to be very effective UV absorbers.

Therefore, the present invention relates to the compounds of the formula:

wherein R-ι, R2, R3, R4, R5, R6, R7 and Re independently of each other are hydrogen; C 1 -C ₁₈ alkyl; C2-C18 alkenyl; C5-C7 cycloalkyl; or C 1 -C 6 alkylene-C 5 -C ₇ cycloalkyl;

Rg is hydrogen; CrC ₁₈ alkyl; C ₂ -C ₈ alkenyl; C5-C7 cyclo5 kyl; C _r C6 alkylene-C ₅ -C ₇ cycloalkyl; or C ₆ -C ₁₀ aryl;

A is -S-; -O- or -NR10-, where R-ιο has the same meanings as R ₉ ;

X is COOR-n! CONR12R13; SO3R14; or SO ₂ NR ₁₅ Ri6, where Rn, R12. R13. R14. R15 θ R16 have, independently of each other, the same gnified symbols as Rg.

Ci-Ci ₈ alkyl indicates straight and branched chain hydrocarbon radicals, for example methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, 2-ethylbutyl, n-pentyl, isopentyl, 1-methylpentyl, 1,3dimethylbutyl, n-hexyl, 1-methylexyl, n-heptyl, isoeptyl, 1,1, 3, 3-tetra15 methylbutyl, 1-methylptyl, 3-methylptyl, n-octyl, 2-ethylexyl, 1 , 1,3-tri-methylexyl, 1,1,3,3-tetramethylpentyl, nonila, decila, undecila, 1-methylundecila, dodecila, tridecila, tetradecila, pentadecila or hexadecila or octadecila.

CrCi ₈ alkyl can be mono- or polysubstituted by C1-C4alkyl, halogen, CN, COOH, COOC-iC ₄ -alkyl, O-Ci-C ₄ -alkyl, NH ₂ or

NO ₂ .

C ₂ -Ci ₈ alkenyl is, for example, allyl, metallyl, isopropenyl, 2-butenyl, 3-butenyl, isobutenyl, n-penta-2, 4-dienyl, 3-methyl-but-2-enyl, noct-2- enyl, n-dodec-2-enyl, isododecenyl, n-dodec-2-enyl or n-octadec-4enyl.

C ₂ -C ₁₈ alkenyl can be mono- or polysubstituted with C-1-C4alkyl, halogen, CN, COOH, COOCrC4-alkyl, O-C1-C4-alkyl, NH ₂ or NO ₂ .

C5-C7 cycloalkyl can be mono- or polysubstituted by C1-C4alkyl, halogen, CN, COOH, COOCrC4-alkyl, OCi-C4-alkyl, NH ₂ or

NO ₂ .

C6-C10 aryl is, for example, phenyl or naphthyl.

Preferred embodiments of the present invention are compounds • · ·

Ζ ¹⁵ of formula (1), where R-ι, R ₂ , R3, R4, R ₅ , R ₆ , R7 θ Rs independently of each other are hydrogen; C1-C-10 alkyl; C ₂ -Cw alkenyl; C5-C7 cycloalkyl; or C1-C4 alkylene-C5-C7 cycloalkyl;

Rg is hydrogen; C1-C10 alkyl; C ₂ -Cio alkenyl; C5-C7 cycloalkyl; C1-C4 alkylene-C ₅ -C ₇ cycloalkyl; naphthyl; or phenyl

A is -S-; -O- or -NR-io-, where R ₁₀ has the same meanings as Rg;

X is COORn; CONR ₁₂ R ₁₃ ; SO3R14; or SO ₂ NRi ₅ R _16> where Rn, R12, R13. R14, R15 θ R16 have the same meanings independently of each other as Rg.

More preferred are compounds of formula (1), in which:

R1, R2, R3, R4, Rs, R6. Rz θ Rs are hydrogen; and

X, Rg and R10 are defined as in formula (1).

Of interest are the compounds of formula (1), in which:

R11, R12, Ri3> R14, R15 θ R16 are hydrogen; or C 1 -C ₂ alkyl; and

Ri, R2, R3, R4, Rs, R6, R7, Rs, Rg, R10 θ X are defined as in formula (1) and more preferably the compounds of formula (1) where:

R-ι, R ₂ , R ₃ , R4, R5, Re, R7 θ Rs are hydrogen;

Rg, R10, R11, R12, R13, R14, R15 θ Hydrogen bond or C1-C12 alkyl; and

X is defined as in formula (1).

Most preferred embodiments are the compounds of the formula:

on what

Rg, A and X have the same meanings as defined in formula (1).

Of particular interest are the compounds of the formula:

on what

Rg is C1-C5 alkyl; and

Ri ₇ is hydrogen; C1-C12 alkyl or -NH ₂ .

A further embodiment of the present invention is a process for preparing compounds of formula (1), characterized by the fact that one mole of at least one compound of the formula:

on what

R1, R ₂ , R3, R4 and Rg have the same meanings independently of each other, as defined in formula (1) and formula (2) and Y is halogen, preferably Cl, is reacted with at least two moles of at least one compound of the formula:

(5) • · ········ · · ·· • ··········· · where R ₅ , R ₆ , Rz, Rs, A and X have independently of each other the same meanings as defined in formula (1) and formula (2).

The reaction is preferably carried out in an inert solvent, for example, dioxane.

The reaction temperature is preferably 50 to 100 ° C, more preferably 60 to 90 ° C.

The reaction product obtained is purified by conventional methods, such as, for example, recrystallization.

The compounds of formula (1) according to the present invention are specifically suitable as UV filters, that is, for protecting organic materials sensitive to ultraviolet light, specifically the skin and hair of humans and animals, from the harmful effects of UV radiation . These compounds are therefore suitable as sunscreens in medical cosmetic, pharmaceutical and veterinary preparations. These compounds can be used in dissolved form and in a micronized state.

The UV absorbers according to the present invention can be used both in the dissolved state (soluble organic filters, solubilized organic filters) and in the micronized state (nanoscale organic filters, particulate organic filters, UV absorber pigments).

Any known process suitable for preparing microparticles can be used to prepare micronized UV absorbers, for example:

- wet grinding (low viscous micronization process for pumpable dispersions), with a hard grinding medium, for example, zirconium silicate spheres in a ball mill and a protective surfactant or a protective polymer in water or an organic solvent appropriate;

- wet kneading (process of high viscous micronization of non-pumped paste) using a continuous or batch (batch) kneader. For a wet kneading process, a solvent (cosmetically acceptable water or oils), a grinding aid (surfactant,

emulsifier) and a polymeric grinding aid can be used.

- the processes can be used respectively

- spray drying an appropriate solvent, for example, aqueous suspensions or suspensions containing organic solvents or true solutions in water, ethanol, dichloroethane, toluene or N-methylpyrrolidone, etc.

- by expansion according to the RESS (Rapid expansion of supercritical solutions) process of supercritical fluids (eg CO ₂ ) in which the UV filter or filters is / are dissolved or the expansion of the fluid carbon dioxide together with a solution of one or more UV filters in an appropriate organic solvent;

- by reprecipitation of appropriate solvents, including supercritical fluids (GASR process = recrystallization of anti-solvent in gas / PCA process = precipitation with compressed anti-solvents).

They can be used as a grinding apparatus for preparing micronized organic UV absorbers, for example, a jet mill, ball mill, vibrating mill or hammer mill, preferably a high speed mixing mill. Even more preferably, the mills are modern ball mills, manufacturers of these types of mill are, for example, Netzsch (LMZ-mill), Drais (DCP-viscous or cosmo flux), Bühler AG (centrifugal mills) or Bachhofer. The grinding is preferably carried out with a grinding aid. Examples of kneading devices for preparing micronized organic UV absorbers are typical sigma-hook batch kneaders, but also series batch kneaders (IKA-Werke) or continuous kneaders (Contiuna de Werner und Pfleiderer).

Low molecular weight grinding aids useful for all the above micronization processes are surfactants and emulsifiers, as described below in emulsifiers and surfactants.

Polymeric grinding aids useful for dispersion in water are water-soluble polymers, cosmetic acceptable with Pm>

• · · ·· · ······ • · ········ · · ·· • · · ··· ······ · ·

5,000 g / mol, for example: Acrylates (Salcare types), modified or unmodified polysaccharides, polyglycosides or xanthan gum. In addition, an alkylated vinylpyrrolidone polymer, a vinylpyrrolidone / vinyl acetate copolymer, an acyl glutamate, an alkyl polyglycoside, cetearet-25 or a phospholipid can be used. Oily dispersions may contain cosmetically acceptable waxy polymers or natural waxes as polymeric grinding aids to adjust viscosity during and after processing.

Useful solvents are water, brine (poly) ethylene glycol or glycerin for water-soluble dispersions and also cosmetically acceptable oils as described in emollients for oil-soluble dispersions.

The micronized UV absorbers thus obtained generally have an average particle size of 0.02 to 2 micrometers, preferably 0.05 to 1.5 micrometer and more specifically 0.1 to 1.0 micrometer.

UV absorbers can also be used dry as a powder. For this purpose, UV absorbers are subjected to known grinding methods, such as vacuum atomization, counter-current spray drying, etc. Such powders have a particle size of 0.1 micrometer to 2 micrometers. To prevent agglomeration from occurring, UV absorbers can be coated with a surface active compound prior to the spraying process, for example, with an anionic, non-ionic or amphoteric surfactant, for example, a phospholipid or a known polymer, such as PVP, an acrylate, etc.

Cosmetic formulations or pharmaceutical compositions according to the present invention can also contain one or more UV filters, as described in tables 1-3.

Cosmetic or pharmaceutical preparations can be prepared by physically mixing UV absorber (s) with the adjuvant using usual methods, for example, by simple stirring together with individual components, especially using the properties • · · · · · ······ • · ···· * ··· · · ·· • ··········· · · for dissolving the already known cosmetic UV absorbers, for example octyl methoxy cinnamate , isooctyl ester of salicylic acid, etc. The UV absorber can be used, for example, without further treatment or in a micronized state or in the form of a powder.

Cosmetic or pharmaceutical preparations contain 0.05-40% by weight, based on the total weight of the composition, of a UV absorber or UV absorber mixtures.

Preference is given to the use of UV absorber mixing ratios of formula (1) according to the invention and optional and additionally light-protecting agents (as described in Tables 1-3) from 1:99 to 99: 1, especially from 1:95 to 95: 1 and preferably from 10:90 to 90:10, based on weight. Of specific interest are mixing ratios from 20:80 to 80:20, especially from 40:60 to 60:40 and preferable and approximately 50:50. Such mixtures can be used, among other things, to improve solubility or increase UV absorption.

The UV absorbers of formula (1) according to the present invention or combinations of UV filters are useful to protect the skin, hair and / or hair color, whether natural or artificial.

Table 1. Suitable UV filter substances that can be additionally used with UV absorbers according to the present invention

Derivatives of p-aminobenzoic acid, for example 4-dimethylaminobenzoic acid 2-ethylhexyl ester;

Derivatives of salicylic acid, for example, 2-ethylhexyl ester of salicylic acid;

Benzophenone derivatives, for example 2-hydroxy-4-methoxybenzophenone and its 5-sulfonic acid derivative;

Dibenzoylmethane derivatives, for example 1- (4-tert-butylphenyl) -3- (4methoxyphenyl) -propane-1,3-dione;

diphenylacrylates, for example 2-ethylexyl 2-cyano-3,3-diphenylacrylate and 3 (benzofuranyl) 2-cyanoacrylate;

3-imidazol-4-ylacrylic acid and esters;

• · • • · • ·· · • · · · · · • · ' • • · · · • · • · · • · · • • · · · · • · • · · · • · • • · · • · • · · · • · · ·

benzofuran derivatives, especially 2- (paminophenyl) benzofuran derivatives, described in EP-A-582 189, US-A-5 338 539, US-A-5 518 713 and EP-A-613893;

polymeric UV absorbers, for example, benzylidene malonate derivatives described in EP-A-709 080;

derivatives of cinnamic acid, for example, 2-ethylhexyl ester of 4-methoxycinnamic acid and isoamyl ester or derivatives of cinnamic acid described in US-A-5 601 811 and WO 97/00851; .

camphor derivatives, for example 3- (4'-methyl) benzylidene-bornan-2-one, 3benzylidene-bornan-2-one, polymer of N- [2 (e 4) -2-oxyborn-3-ylidene-methyl ) benzyljacrilamide, 3- (4'-trimethylammonium) -benzylidene-boman-2-one methyl sulfate, 3,3 '- (1,4-phenylenedimethine) -bis (7,7-dimethyl-2-oxo-bicyclic acid [2.2.1] heptane-1-methanesulfonic) and salts, 3- (4-sulfo) benzylidene-bornan-2-one and salts; camphorbenzalkonium methosulfate;

hydroxyphenyltriazine compounds, for example 2- (4'-methoxyphenyl) -4,6-bis (2'hydroxy-4'-n-octyloxyphenyl) -1,3,5-triazine; 2,4-bis {[4- (3- (2-propyloxy) -2-hydroxypropyloxy) -2-hydroxy] -phenyl) -6- (4-methoxyphenyl) -1, 3,5-triazine; 2,4-bis {[4- (2-ethylhexyloxy) -2-hydroxy] -phenyl} -6- [4- (2-methoxyethyl-carboxyl) -phenylamino] -1,3,5triazine; 2,4-bis {[4- (tris (trimethylsilyloxy-silylpropyloxy) -2-hydroxy] -phen |} -6- (4methoxyphenyl) -1, 3,5-triazine; 2,4-bis {[4- ( 2-methylpropenyloxy) -2-hydroxy] -phenyl} -6 (4-methoxyphenyl) -1,3,5-triazine; 2,4-bis {[4- (1 ', 1', r, S ^ õ ^ S ^ õ-heptamethyltrisylyl2-methyl-propoxy) -2-hydroxy] -phenyl} -6- (4-methoxyphenyl) -1,3,5-triazine; 2,4-bis {[4 (3- (2 -propyloxy) -2-hydroxy-propyloxy) -2-hydroxy] -phenyl} -6- [4-ethylcarboxy) phenylamino] -1,3,5-triazine;

benzotriazole compounds, for example 2,2'-methylene-bis (6- (2Hbenzotriazol-2-yl) -4- (1,1,3,3-tetramethylbutyl) -phenol;

trianilino-s-triazine derivatives, for example 2,4,6-trianiline- (p-carbo-2'-ethyl1 '-oxy) -1,3,5-triazine and the UV absorbers described in US-A- 5,332,568, EP-A-517 104, EP-A-507 691, WO93 / 17002 and EP-A-570 838;

2-phenylbenzimidazole-5-sulfonic acid and salts thereof;

menthol o-aminobenzoates;

physical sunscreens coated or not, such as titanium dioxide, oxide • · ········ · · ·· • · · ··· ······ · · zinc, iron oxides, mica , MnO, Fe2O _3, Ce2O _3, Al2O3, ZrC> 2. (Surface coatings: polymethylmethacrylate, methicone (methylhydrogen-polysiloxane as described in CAS 9004-73-3), dimethicone, isopropyl titanium tri-stearate (as described in CAS 61417-49-0), metal soaps, such as magnesium stearate (as described in CAS 4086-70-8), perfluorphosphate alcohol such as, C9-15 fluorphosphate alcohol (as described in CAS 74499-44-8; JP 5-86984, JP 4-330007)). The primary particle size is an average of 15 nm-35 nm and the particle size in the dispersion is in the range of 100 nm - 300 nm.

Aminohydroxy-benzophenone derivatives described in DE 10011317, EP 1133980 and EP1046391

Phenyl-benzimidazole derivatives as described in EP 1167358 The UV absorbers described in Sunscreens, Eds. N.J. Lowe, N. A. Shaath, Marcei Dekker, Inc., New York and Basle or in Cosmetics & Toiletries (107), 50ff (1992) can also be used as additional UV protective substances.

Table 2 - Suitable UV filter substances that can be additionally used with UV absorbers, according to the present invention, are described in the following patents (Abbreviations T: table, R: row, Comp: Compound, Ex: compound (s) of the patent example, p: page)

DE 100331804 Tab 1 p 4, tab 2 + 3 p 5 EP 613893 Ex1-5 + 15, T1, pp6-8 EP 1000950 Compound in Table 1, pp 18-21 EP 1005855 T3, p13 EP 1008586 Ex 1-3, pp 13-15 EP 1008593 Ex 1-8, pp4-5 EP 1027883 Compound VII, p 3 EP 1027883 Comp l-VI, p 3 EP 1028120 Ex 1-5, pp 5-13 EP 1059082 Ex 1; T 1, pp 9-11

• · ······ »· · · ·· • ··········· · · ·

EP 1060734 T 1-3, pp 11-14 EP 1064922 Compounds 1-34, pp 6-14 EP 1081140 Ex 1-9, pp 11-16 EP 1103549 Compounds 1-76, pp 39-51 EP 1108712 4,5-dimorpholino-3-hydroxypyridazine EP 1123934 T3, p10 EP 1129695 Ex 1-7, pp 13-14 EP 1167359 Ex 1 p11 and ex 2 p 12 EP 420707 B1 Ex 3, p 13 (CAS number 80142-49-0) EP 503338 T1, pp9-10 EP 517103 Ex 3,4,9,10 pp 6-7 EP 517104 Ex 1, T 1, pp 4-5; Ex 8, T 2, pp 6-8 EP 626950 All compounds EP 669323 Ex1-3, p5 EP 780382 Ex 1-11, pp 5-7 EP 823418 Ex 1-4, pp 7-8 EP 826361 T 1, pp 5-6 EP 832641 Ex 5 + 6 p 7; t 2, p 8 EP 832642 Ex 22, T 3 pp, 10-15; T 4, p 16 EP 852137 T2, pp 41-46 EP 858318 T1, p6 EP 863145 Ex 1-11, pp 12-18 EP 895776 Compounds in row 48-58, p 3; R 25 + 33, p 5 EP 911020 T2, p 11-12 EP 916335 T2-4, pp 19-41 EP 924246 T 2, p 9 EP 933376 Ex 1-15, pp 10-21 EP 944624 Ex 1 + 2, pp13-15 EP 945125 T 3 a + b, pp 14-15 EP 967200 Ex 2; T3-5, pp 17-20 EP 969004 Ex 5, T 1, pp 6-8

• ········ · · ·· ············ · · · • · ············

JP 2000319629 CAS registration number 80142-49-0, 137215-83-9, 307947-82-6 US 5635343 All compounds on pp 5-10 US 5338539 Ex 1 -9, pp 3 + 4 US 5346691 Ex 40, p 7; T 5, p 8 US 5801244 Ex1-5, pp6-7 WO 0149686 Ex 1-5, pp 16-21 WO 0168047 Tables on pp 85-96 WO 0181297 Ex 1-3 pp 9-11 WO 0238537 All p 3 compounds, compounds in row 1-10 p 4 WO 9217461 Ex 1-22, pp 10-20 WO 9220690 Polymeric compounds in examples 3-6 WO 9301164 T1 + 2, pp 13-22 WO 9714680 Ex 1-3, p10

Table 3. Suitable UV filter substances that can be used in addition with UV absorbers, according to the present invention

No. chemical name Number CAS 1 (+/-) - 1,7,7-trimethyl-3 - [(4-methylphenyl) methylene] bicyclo- [2.2.1] heptan-2-one 36861-47-9 2 1,7,7-trimethyl-3- (phenylmethylene) bicycle [2.2.1] heptan-2-one 15087-24-8 3 (2-Hydroxy-4-methoxyphenyl) (4-methylphenyl) methanone 1641-17-4 4 2,4-dihydroxybenzophenone 131-56-6 5 2,2 ', 4,4'-tetrahydroxybenzophenone 131-55-5 6 2-Hydroxy-4-methoxy benzophenone 131-57-7 7 2-Hydroxy-4-methoxy benzophenone-5-sulfonic acid 4065-45-6 8 2,2'-dihydroxy-4,4'-dimethoxybenzophenone 131-54-4 9 2,2'-Dihydroxy-4-methoxybenzophenone 131-53-3 10 Alpha- (2-oxoborn-3-ylidene) toluene-4-sulfonic acid and its salts 56039-58-8 11 1- [4- (1,1-dimethylethyl) phenyl] -3- (4-methoxyphenyl) propane-1,3-dione 70356-09-1 12 Methyl sulfate N, N, N-trimethyl-4 - [(4,7,7-trimethyl-3- oxobicycles [2.2.1] hept-2-ylidene) methyl] anilinium 52793-97-2 22 3,3,5-Trimethylcyclohexyl-2-hydroxy benzoate 118-56-9 23 Isopentyl P-methoxycinnamate 71617-10-2

• · ······> · · · · * • * · ··· ······ · · · •············· • · ······ «

NÇ auímica denomination Number CAS 1 (+/-) - 1,7,7-trimethyl-3 - [(4-methylphenyl) methylene] bicyclo- [2.2.1] heptan-2-one 36861-47-9 27 menthol o-aminobenzoate 134-09-8 28 Mentil salicylate 89-46-3 29 2-Ethylexyl 2-cyano, 3,3-diphenylacrylate 6197-30-4 30 2-ethylexyl 4- (dimethylamino) benzoate 21245-02-3 31 2-ethylexil 4-methoxycinnamate 5466-77-3 32 2-Ethylexyl salicylate 118-60-5 33 Benzoic acid, 4,4 ', 4- (1,3,5-triazine-2,4,6-triyltriimino) tris-, ester tris (2-ethylexyl); 2,4,6-Trianilino- (p-carbo-2'-ethylexil-r-oxy) -1,3,5-triazine 88122-99-0 34 4-Aminobenzoic acid 150-13-0 35 Benzoic acid, 4-amino-, ethyl ester, polymer with oxirane 113010-52-9 38 2-Phenyl-1 H-benzimidazole-5-sulfonic acid 27503-81-7 39 2-Propenamide, N - [[4 - [(4,7,7-trimethyl-3-oxobicyclo [2.2.1] hept-2- ilidene) methyl] phenyl] methyl] -, homopolymer 147897-12-9 40 Triethanolamine salicylate 2174-16-5 41 3,3 '- (1,4-phenylenedimethylene) bis [7,7-dimethyl-2-oxo- bicycle [2.2.1] heptane-1-methanesulfonic] 90457-82-2 42 Titanium dioxide 13463-67-7 44 Zinc oxide 1314-13-2 45 2,2'-Methylene-bis- [6- (2H-benzotriazol-2-yl) -4- (1,1,3,3-tetramethyl-butyl) - phenol] 103597-45-1 46 2,4-bis {[4- (2-ethylexyloxy) -2-hydroxy] -phenyl} -6- (4-methoxyphenyl) - (1, 3,5) - triazine 187393-00-6 47 1H-Benzimidazole-4,6-disulfonic acid, 2,2 'disodium salt - (1,4- phenylene) bis 180898-37-7 48 Benzoic acid, 4,4 '- [[6 - [[4 - [[(1,1-dimethylethyl) amino] carbonyl] phenyl] amino] 1,3,5-triazine-2,4-diyl] diimino] bis - bis (2-ethylhexyl) ester 154702-15-5 49 Phenol, 2- (2H-benzotriazol-2-yl) -4-methyl-6- [2-methyl-3- [1,3,3,3-tetramethyl-1 - [(trimethylsilyl) oxy] disiloxanii] propyl] - 155633-54-8 50 alpha- (trimethylsilyl) -mega- (trimethyl-silyloxy) poly [oxide (dimethyl) -silylene] -co- [oxy (methyl) (2- {p- [2,2-bis (ethoxycarbonyl) vinyl] -phenoxy} -1 methylene- ethyl) silylene] -co- [oxy (methyl) (2- {p- [2,2-bis (ethoxycarbonyl) vinyl] phenoxy} prop-1- enyl) silylene] 207574-74-1 51 Benzenesulfonic acid, 3- (2H-benzotriazol-2-yl) -4-hydroxy-5- (1- methylpropyl) -, monosodium salt 92484-48-5

······· »·· * · · • · ····· * ·····

NÇ auímica denomination Number CAS 1 (+/-) - 1,7,7-trimethyl-3 - [(4-methylphenyl) methylene] bicyclo- [2.2.1] heptan-2-one 36861-47-9 52 Benzoic acid, 2- [4- (diethylamino) -2-hydroxybenzoyl] -, hexyl ester 302776-68-7 53 1-Dodecanamine, N- [3 - [[4- (dimethylamino) benzoyl] amino] -propyl] N, N- dimethyl-, salt with 4-methylbenzenesulfonic acid (1: 1) 156679-41-3 54 1-Propanamine, N, N, N-trimethyl-3 - [(1-oxo-3-phenyl-2-propenyl) -amino] -, chloride 177190-98-6 55 1H-Benzimidazole-4,6-disulfonic acid, 2,2 '- (1,4-phenylene) bis- 170864-82-1 56 1,3,5-Triazine, 2,4,6-tris (4-methoxyphenyl) - 7753-12-0 57 1,3,5-Triazine, 2,4,6-tris [4 - [(2-ethylexyl) oxy] phenyl] - 208114-14-1 58 1-Propanamine, 3 - [[3- [3- (2H-benzotriazol-2-yl) -5- (1,1-dimethylethyl) -4- hydroxyphenyl] -1-oxopropyl] amino] -N, N-diethyl-N-methyl-, methyl sulfate (salt) 340964-15-0 59 2-Propenoic acid, 3- (1H-imidazol-4-yl) - 104-98-3 60 Benzoic acid, 2-hydroxy-, methyl ester [4- (1-methylethyl) phenyl] 94134-93-7 61 1,2,3-Propanotriol, 1- (4-aminobenzoate) 136-44-7 62 Benzenoacetic acid 3,4-dimethoxy-a-oxo- 4732-70-1 63 2-propenoic acid, 2-cyano-3,3-diphenyl-, ethyl ester 5232-99-5

Suitable UV filter substances, which can be additionally used with UV absorbers according to the present invention, are any UV-A and UV-B filter substances.

Cosmetic or pharmaceutical preparations can be, for example, creams, gels, lotions, alcoholic and aqueous / alcoholic solutions, emulsions, wax / grease compositions, stick preparations, powders or ointments. In addition, the UV filters mentioned above, cosmetic or pharmaceutical preparations may contain additional adjuvants, as described below.

As emulsions containing water and oil (for example, water-oil, oil-water, oil-water-oil and water-oil-water emulsions or microemulsions) the preparations contain, for example, 0.1 to 30% by weight , preferably from 0.1 to 15% by weight and especially from 0.5 to 10% by weight, based on the total weight of the composition, of one or more UV absorbers, from 1 to 60% by weight, especially 5 to 50% by weight and preferably

from 10 to 35% by weight, based on the total weight of the composition, of at least one oily component, from 0 to 30% by weight, especially from 1 to 30% by weight and preferably from 4 to 20% by weight, with based on the total weight of the composition, at least one emulsifier, from 10 to 90% by weight, especially from 30 to 90% by weight, based on the total weight of the composition, from water and from 0 to 88.9% by weight , especially from 1 to 50% by weight of additional cosmetically acceptable adjuvants.

The cosmetic or pharmaceutical compositions / preparations according to the invention can also contain one or more additional compounds, as described below.

Fatty alcohols

Guerbert alcohols based on fatty alcohols having from 6 to 18, preferably 8 to 10 carbon atoms including cetyl alcohol, stearyl alcohol, cetearyl alcohol, oleyl alcohol, octyl dodecanol, C12-C15 alcohols, acetylated lanolin alcohol, etc. .

Fatty acid esters

Esters of linear C ₆ -C24 fatty acids with C3-C24 linear alcohols, esters of C6-C ₁₃ carboxylic acids branched with linear C6-C24 fatty alcohols, esters of linear C6-C24 fatty acids with branched alcohols, especially 2-ethylexanol, esters of hydroxycarboxylic acids with C6-C22 linear or branched fatty alcohols, especially dioctyl malates, esters of linear and / or branched fatty acids with polyhydric alcohols (eg propylene glycol, diol dimer or triol trimer) and / or Guerbet alcohols, for example, caprylic acid, caprylic acid, 2-ethylexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isosteric acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, elasto-stearic acid, arachidic acid, gadoleic acid, behenic acid and erucic acid and mixtures of their technical classification (obtained, for example, in rem pressure option of natural fats and oils, reduction of Roelen oxosynthesis aldehydes or dimerization of unsaturated fatty acids) with alcohols, for example, isopropyl alcohol, alcohol ** · · · · · »c β ·· ··· • · · «·« ····· · · · · • ♦ ··········· · e • · »· * ····· * · t ·· capróico, caprylic alcohol, 2-ethylexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, pretroselinic alcohol, linoyl alcohol, linolenic alcohol, elasto-stearyl alcohol, arachidyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol and brassidyl alcohol and mixtures of their technical classification (obtained for example, in the high pressure hydrogenation of methyl esters of technical classification based on fats and oils or Roelen oxosynthetic aldehydes and as monomeric fractions in dimerization of fatty alcohols in10 satur ados).

Examples of such steric oils are isopropylmiristate, isopropylpalmitate, isopropyl stearate, isopropyl isostearate, isopropyloleoate, n-butyl stearate, n-hexyl laurate, n-decyloleate, isooctyl stearate, iso-nonyl stearate, isonyl stearate, 2-isonyl-stonate, isonylone laurate,

2-hexyldecylstearate, 2-octylododecylpalmitate, oleyloleate, oleilerucate, erucyloleate, erucyl erucate, cetearyl octanoate, cetyl palmitate, cetyl stearate, cetyl oleate, cetyl behenate, cetyl acetate, myristyl myristyl, myristyl myristyl myristyl myristyl , myristyl lactate, propylene glycol tipprilat / caprate, stearyl heptanoate, diiso-stearyl malate, octyl hydroxystea20 rat, etc.

Other adjuvants

Diethylexil 2,6-naphthalate, di-n-butyl adipate, di (2-ethylexyl) -adipate, di (2-ethylexyl) -succinate and diisotridecyl acetate and also diol esters, such as ethylene glycol dioleate, ethylene glycol diisotridecanoate , propylene glycol di (2-ethylexanoate), propylene glycol diisoestearate, propylene glycol dipellarate, butanediol diisoestearate and neopentyl glycol tipprilate. C6C ₂ esters 4 fatty alcohols and / or Guerbet alcohols with aromatic, saturated and / or unsaturated carboxylic acids, especially benzoic acid, esters of dicarboxylic C2-C12 acids with linear or branched alcohols having from 1 to 22 carbon atoms or polyols having from 2 to 10 carbon atoms and from 2 to 6 hydroxy groups.

··· ··· • · · · ··· ······ · · · · · ············ • · ·> ·····

Natural or synthetic triglycerides including glyceryl esters and derivatives

Di or triglycerides based on C6-Cig fatty acids, modified by reaction with other alcohols (caprylic / capric triglyceride, wheat germ glycerides, etc.). Polyglycerin fatty acid esters (polyglyceryl-n, such as polyglyceryl-4 caprate, polyglyceryl-2 isostearate, etc. or castor oil, hydrogenated vegetable oil, sweet almond oil, wheat germ oil, sesame oil, hydrogenated cottonseed oil, coconut oil, avocado oil, kernel oil, hydrogenated castor oil, shea butter, cocoa butter, soybean oil, vision oil, sunflower oil, macadamia oil, olive oil , hydrogenated tallow, apricot seed oil, hazelnut oil, borago oil, etc.

Waxes including esters of long chain acids and alcohols as well as compounds having wax-like properties, for example, carnauba wax, beeswax (white or yellow), lanolin wax, candelilla wax, ozocerite, Japanese wax, paraffin wax , microcrystalline wax, ceresin, cetearyl esters wax, synthetic beeswax, etc. Also, hydrophilic waxes such as cetearyl alcohol or partial glycerides.

Pearlizing waxes:

Alkylene glycol esters, especially ethylene glycol distearate; fatty acid alkanolamides, especially coconut fatty acid diethanolamide; partial glycerides, especially stearic acid monoglycerides; esters of polyvalent carboxylic acids, substituted by hydroxy or unsubstituted with fatty alcohols having from 6 to 22 carbon atoms, especially long chain esters of tartaric acid; fatty substances, for example, fatty alcohols, fatty ketones, fatty aldehydes, fatty ethers and fatty carbonates, which, in total, have at least 24 carbon atoms, especially laurone and distearyl ether; fatty acids such as stearic acid, hydroxystearic acid or behenic acid, olefin epoxide ring opening products having 12 to 22 carbon atoms with fatty alcohols having 12 to 22 carbon atoms and / or polyols having 2 to 15 carbon atoms and 2 to 10 hydroxy groups and mixtures thereof.

• · · · · · ··· · · · ·· ········ · ·

Hydrocarbon oils

Mineral oil (light or heavy), petrolatum (yellow or white), microcrystalline wax, paraffinic and isoparaffinic compounds, hydrogenated isoparaffinic molecules such as polydecenes and polybutene, hydrogenated polyisobutene, squalane, isoexadecane, isododecane and others from the plant and animal kingdom.

Silicones and siloxanes (substituted organo polysiloxanes)

Dimethylpolysiloxanes, methylphenylpolysiloxanes, cyclic silicones and also silicone compounds modified with amino, fatty acid, alcohol, polyether, epoxy, fluorine, glycoside, and / or alkyl, which at room temperature can be both liquid and resinous. Linear polysiloxanes, dimethicone (Dow Corning 200 fluid, Rhodia Mirasil DM), dimethicone, cyclic silicone fluids, volatile cyclopentasiloxanes (Dow Corning 345 fluid), phenyltrimethicone (Dow Corning 556 fluid). Also suitable are simethics, which are mixtures of dimethicones having an average chain length of 200 to 300 units of dimethylsiloxane with hydrogenated silicates. A detailed examination by Todd and others of suitable volatile silicones can be found further in Cosm. Toil. 91, 27 (1976).

Fluorinated or perfluorinated oils

Perfluorexane, dimethylcyclohexane, ethylcyclopentane, polyiperfluormethylisopropyl ether.

Emulsifiers

Any conventionally usable emulsifier can be used in the compositions. Emulsifying systems can comprise, for example, carboxylic acids and their salts: alkaline sodium, potassium and ammonium soap, metallic calcium or magnesium soap, organic based soap, such as lauric, palmitic, stearic and oleic acid, etc. Alkyl phosphates or phosphoric acid esters, acid phosphate, diethyl phosphate 30 lamina, cetyl potassium phosphate Ethoxylated carboxylic acids or polyethylene glycol esters, PEG-n acylates. Linear fatty alcohols having 8 to 22 carbon atoms, branched from 2 to 30 moles of ethylene oxide and / or

to 5 moles of propylene oxide with fatty acids having 12 to 22 carbon atoms and with alkyl phenols having 8 to 15 carbon atoms in the alkyl group. Fatty alcohol polyglycol ether such as, lauret-n, cetearet-n, estearet-n, olet-n. Polyglycol ether of fatty acid such as, PEG-n stearate, PEG-n oleate, PEG-n cocoate. Monoglycerides and polyol esters. C12-C22 mono fatty acid and diesters of addition products from 1 to 30 moles of ethylene oxide with polyols. Polyglycerol ester and fatty acid such as, glycerol monostearate, diisoestearoyl polyglyceryl-3-diisoestearates, polyglyceryl-3-diisoestearates, triglyceryl diisoestearates, polyglyceryl-2-sesquiisoestearates or polyglyceryl dimerates. Mixtures of compounds from various other classes of substances are also suitable. Polyglycol fatty acid esters such as diethylene glycol monostearate, polyethylene glycol esters and fatty acids, sucrose esters and fatty acid, such as bag esters, glycerol and sucrose esters, such as bag glycerides. Sorbitol and sorbitan, mono and sorbitan diesters of saturated and unsaturated fatty acids having 6 to 22 carbon atoms and ethylene oxide addition products. Polysorbate-n series, sorbitan esters, such as sesquiiso-stearate, PEG- (6) -sorbitan isostearate, PEG- (10) -sorbitan laurate, PEG-17 sorbitan dioleate. Glucose derivatives, C8-C22 alkyl mono and oligoglycosides and glucose ethoxylated analogues being preferred as the sugar component. Oil-water emulsifiers, such as methyl glucet-20 sesquiestearate, sorbitan stearate / sucrose cocoate, methyl glucose sesquiestearate, cetearyl alcohol / cetearyl glycoside. Water-oil emulsifiers, such as methyl glucose dioleate / methyl glucose isostearate. Sulfates and sulfonated derivatives, dialkylsulfosuccinates, dioctyl succinate, alkyl lauryl sulphonate, linear sulphonated paraffins, sulphonated tetrapropylene sulphonate, sodium lauryl sulphates, ammonium lauryl sulphates and ethanolamine, lauryl ether sulphates, sodium laureth sulphates, sulphatesuccinates acetyl, alkanolamide sulfates, taurines, methyl taurines, imidazole sulfates. Amine derivatives, amine salts, ethoxylated amines, amine oxide with chains containing a heterocycle, such as alkyl imidazolines, pyridine derivatives, isoquinoteins, cetyl pyri chloride20

dinium, cetyl pyridinium bromide, quaternary ammonium, such as cetyltrimethyl boron ammonium bromide (CTBA), stearyl alkonium. Amide derivatives, alkanolamides, such as DEA acylamide, ethoxylated amides, such as PEG-n acylamide, amide oxide. Polysiloxane / polyalkyl / polyether copolymers and derivatives, dimethicone, copolyols, polyethylene silicone oxide copolymer, silicone glycol copolymer. POE-n ethers or propoxylates (Meroxapols), polaxamers or poly (oxyethylene) m-block-poly (oxypropylene) n-block (oxyethylene). Zwitterionic surfactants that carry at least one quaternary ammonium group and at least one carboxylate and / or sulfonate group in the molecule. The zwitterionic surfactants that are especially suitable are betaines, such as N-alkylΝ, Ν-dimethylammonium glycinates, cocoalkyl dimethylammonium glycinate, N-acylamino-propyl-N glycinates, N-dimethylammonium, cocoacylaminopropyl dimethylammonyl glycinate and 2 3-carboxymethyl-3-hydroxyethylimidazolines, each having 8 to 18 carbon atoms in the alkyl or acyl group and also cocoacylaminoethylhydroxyethylcarboxy methyl, N-alkylbetaine, N-alkylaminobetaines. Alkylimidazolines, alkylopeptides, lipoamino acids, self-emulsifying bases and compounds as described in K.F.DePolo, A short textbook of cosmetology, Chapter 8, Tables 8-7, pages 250-251.

Non-ionic bases, such as PEG-6 (e) beeswax PEG-6 (e) polyglyceryl 2-isostearate [Apifac], glyceryl stearate (e) PEG-100 stearate. [Arlacel 165], PEG-5 glyceryl stearate [arlatone 983 S], sorbitan oleate (e) polyglyceryl-3 ricinoleate [Arlacel 1689], sorbitan stearate and sucrose cocoate [Arlatone 2121], glyceryl stearate and lauret -23 [Cerasynth 945], cetearyl alcohol and cetet-20 [Cetomacrogol wax], cetearyl alcohol and colissorbate 60 and PEG-150 and stearate-20 [Polawax GP 200, Polawax NF], cetearyl alcohol and cetearyl polyglycoside [Emulgade PL 1618] , cetearyl alcohol and cetearet-20 [Emulgade 1000NI, Cera Cosmo], cetearyl alcohol and castor oil PEG-40 [Emulgade F Special], cetearyl alcohol and castor oil PEG-40 and sodium cetearyl sulfate [Emulgade F], alcohol stearyl and estearet-7 and estearet-10 [Emulgator E 2155], cetearyl alcohol and estearet-7 and estearet-10 (US emulsifying wax

NF], glyceryl stearate and PEG-75 stearate [Gelot 64], propylene glycol acetate cetet-3 [Hetester PCS], propylene glycol acetate isocet-3 [Hetester PHA], cetearyl alcohol and cetet-12 and olet-12 [Lanbritol N21 wax], PEG-6 stearate and PEG-32 stearate [Tefose 1500], PEG-6 and cetet-20 and stearet-20 [Tefose 2000], PEG-6 and cetet-20 stearate and glyceryl stearate and stearet-20 [Tefose 2561], glyceryl stearate and cetearet-20 [Teginacid H, C, X].

Anionic alkaline bases such as, PEG-2 SE stearate, glyceryl stearate SE [Monelgine, Cutina, KD], propylene glycol stearate [Tegin P]. Anionic acid bases, such as cetearyl alcohol and sodium cetearyl sulfate [Lanette N, Cutina LE, Crodacol GP], cetearyl alcohol and sodium lauryl sulfate [Lanette W], trilanet-4 phosphate and glycol stearate and PEG- stearate 2 [Sedefos 75], glyceryl stearate and sodium lauryl sulfate [Teginacid Special]. Cationic acid bases, such as cetearyl alcohol and cetrimony bromide.

Emulsifiers can be used in an amount of, for example, 1 to 30% by weight, especially from 4 to 20% by weight and preferably from 5 to 10% by weight, based on the total weight of the composition.

When formulated in oil-water emulsions, the preferred amount of such an emulsifying system would represent 5% to 20% of the oil phase.

Additives and additives

Cosmetic / pharmaceutical preparations, for example, creams, gels, lotions, alcoholic and aqueous / alcoholic solutions, emulsions, wax / fat compositions, stick preparations, powders or ointments may also contain, as adjuvants and additional additives, mild surfactants , super-greasing agents, consistency regulators, thickeners, polymers, stabilizers, active biogenic ingredients, active deodorizing ingredients, anti-dandruff agents, film-forming agents, swelling agents, additional UV-protective factors, antioxidants, hydrotropic agents, preservatives, insect repellents , self-tanning agents, solubilizers, perfumed oils, dyes, • bacteria-inhibiting agents and the like.

Super-greasing agents

Substances suitable for use as super-greasing agents are, for example, lanolin and lecithin and also polyethoxylated or acrylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides, the latter acting simultaneously as foam stabilizers.

Surfactants

Examples of suitable mild surfactants, that is, surfactants especially well tolerated by the skin include, fatty alcohol polyglycol ether sulfates, monoglyceride sulfates, mono and / or di-alkyl sulfosuccinates, fatty acid isethionates, fatty acid sarcosinates, taurides of fatty acid, fatty acid glutamates, aolefin sulfonates, ethercarboxylic acids, alkyl oligoglycosides, fatty acid glucamides, alkylamidobetaines and / or protein fatty acid condensation products, the latter preferably based on wheat proteins. Consistency / thickeners and rheology modifiers

Silicon dioxide, magnesium silicates, aluminum silicates, polysaccharides or derivatives thereof, for example, hyaluronic acid, xanthan gum, guar guar, agar agar, alginates, carrageenan, gelan, pectins, or modified cellulose such as hydroxycellulose, hydroxypropylmethylcellulose. In addition, the polyacrylates or homopolymer of cross-linked acrylic acids and polyacrylamides, carbomer (types carbopol 980, 981, 1382, ETD 2001, ETD2020, Ultrez 10) or Salcare range, such as Salcare SC80 (estearet-10 allyl ether / acrylates copolymers) ), Salcare SC81 (acrylate copolymer), Salcare SC91 and Salcare AST (sodium acrylate copolymer / PPG-1 tridecet-6), sepigel 305 (polyacrylamide / lauret-7), Simulgel NS and Simulgel EG (hydroxyethyl acrylate / copolymer) acrylamyldimethyl sodium taurate), Stabilen 30 (cross-acrylate polymer / vinyl isodecanoate), Permulen TR-1 (cross-acrylate polymer / Cio-30 alkyl acrylate), Luvigel EM (sodium acrylate copolymer), Aculyn 28 (copolymer of sodium acrylates) acrylates / behenet-25 methacrylate).

Polymers

Suitable cationic polymers, for example, cationic cellulose derivatives, for example, a quaternized hydroxymethyl cellulose obtained under the trademark Amerchol Polymer JR 400, cationic starches, copolymers of dialylamonium salts and acrylamides, quaternized vinylpyrrolidone / vinyl polymers, for example , Luviquat® (BASF), condensation products of polyglycols and amines, quaternized collagen polypeptides, for example, hydrolyzed hydroxypropyl lauryl-dimonium collagen (Lamequat®L / Grünau), quaternized wheat polypeptides, polyethyleneimine, cationic silicone polymers, by example, amidomethicones, adipic acid and dimethylaminohydroxypropylethylenetriamine copolymers (Cartaretin / Sandoz), acrylic acid copolymers with dimethyldialylammonium chloride (Merquat 550 / Chemviron), polyamino polyamides, as described, for example, in FR-A-2 252 reticulated water, derived from cationic chitin, for example chi quaternized tosan, optionally distributed as microcrystals; condensation products of dialoalkyls, for example, dibromobutane, with bisdialkylamines, for example, bisdimethyl-amino-1,3-propane, cationic guar gum, for example Jaguar C-17, Jaguar C-16 by Celanese, salt polymers of quaternary ammonium, for example, Mirapol A-15, Mirapol AD-1, Mirapol AZ-1 by Miranol. As anionic, zwitterionic, amphoteric and non-ionic polymers can be taken into account, for example, vinyl acetate / crotonic acid copolymers, vinylpyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate copolymers / isobomyl acrylate, copolymers methyl vinyl ether / maleic anhydride and esters thereof, non-cross-linked polyacrylic acids and polyols cross-linked with polyols, acrylamidopropyl-trimethyl-ammonium chloride copolymers, octyl acrylate / methyl-methacrylate-acrylate-methylacrylate-copolymer polyvinyl-pyrrolidone, vinylpyrrole30 dona / vinyl acetate, vinylpyrrolidone / dimethylaminoethyl methacrylate / vinyl caprolactam terpolymers and also optionally, derivatized cellulose ethers and silicones. In addition, polymers as described in • · · · ······ • · · · · · • · · ·

• · · ·

EP 1093796 (pages 3-8, paragraphs 17-68) can be used.

Biogenic active ingredients

Biogenic active ingredients should be understood as meaning, for example, tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, deoxyribonucleic acid, retinol, bisabolol, allantoin, phyanthriol, pantrenol, AHA acids, amino acids, ceramides, essential oils, pseudoceramides plant extracts and vitamin complexes.

Deodorant active ingredients

As active deodorizing ingredients, antiperspirants, for example, aluminum chlorohydrates, are taken into account (see, J. Soc. Cosm. Chem. 24, 281 (1973)). It is commercially available under the trademark Locron® of Hoechst AG, Frankfurt (FRG) for example, an aluminum chlorohydrate corresponding to the formula AbíOHjõCI x 2.5 H ₂ The use of it is specifically preferred (see J. Pharm. Pharmacol. 26, 531 (1975)). In addition to chlorohydrates, it is also possible to use aluminum hydroxyacetates and acid aluminum / zirconium salts. Esterase inhibitors can be added as additional deodorant active ingredients. Such inhibitors are preferably trialkyl citrates, such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate and especially triethyl citrate (Hydagen CAT, Henkel), which inhibit the enzyme activity and consequently reduce the formation of odor. Additional substances that are taken into account as esterase inhibitors are sterol sulfates or phosphates, for example, lanoesterol, cholesterol, campestrol, stigmaesterol and sitoesterol sulfate or phosphate, dicarboxylic acids and esters, such as, for example, glutaric acid, monoethyl ester glutaric acid, glutaric acid diethyl ester, adipic acid, adipic acid monoethyl ester, adipic acid diethyl ester, malonic acid and malonic acid diethyl ester and hydroxycarboxylic acids thereof, for example, citric acid, malic acid, tartaric acid or tartaric acid diethyl ester. Antibacterial active ingredients that influence germ flora and kill or inhibit the growth of sugar-decomposing bacteria

way, be present in the preparations (especially in stick preparations). Examples include chitosan, phenoxyethanol and chlorhexidine gluconate. 5-chloro-2- (2,4-dichlorophenoxy) -phenol (Triclosan, Irgasan, Ciba Specialty Chemicals Inc.) has also proved to be especially effective.

Anti-dandruff agents

As anti-dandruff agents, for example, climbazole, octopirox and zinc pyrithione can be used. Usual film-makers include, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone copolymers, vinylpyrrolidone / vinyl acetate, quaternary cellulose derivative polymers containing a high proportion of acrylic acid, collagen, hyaluronic acid and salts thereof, in addition similar compounds.

Antioxidants

In addition to the primary substances that protect against light, it is also possible to use secondary substances that protect against light of the antioxidant type that interrupt the photochemical reaction chain triggered when UV radiation penetrates the skin or hair. Typical examples of such antioxidants are amino acids (eg, glycine, histidine, tyrosine, tryptophan) and derivatives thereof, imidazoles (eg, urocanic acid) and derivatives thereof, such as, D, L-carnosine, Dcarnosine, L-carnosine and derivatives thereof (eg, anserine), carotinoids, carotenes, lycopene and derivatives thereof, chlorogenic acid and derivatives thereof, lipoic acid and derivatives thereof (eg dihydrolipoic acid), aurothioglycosis, propylthiouracil and others thiols (for example, thioredoxin, glutathione, cysteine, cystine, cystamine and glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl, lauryl, palmitoyl, oleyl, linoleyl, cholesteryl and glycerol esters thereof) and also salts of them, dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and derivatives thereof (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) and also sulfoximine compounds (for example o, butionin sulfoximines, homocysteine sulfoximine, butionin sulfones, penta, hexa, heptathionine sulfoximine), also chelating agents (me-

• thallic) (eg hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), hydroxy acids (eg citric acid, lactic acid, malic acid), humic acid, bile acid, bile extracts, bilirubin, biliverdin, EDTA, EDDS and EGTA and derivatives thereof, unsaturated fatty acids and derivatives thereof (linolenic acid, linoleic acid, oleic acid), folic acid and derivatives thereof, ubiquinone and ubiquinol and derivatives thereof, for example vitamin C and derivatives , ascorbyl palmitate, ascorbyl magnesium phosphate, ascorbyl acetate), tocopherols and derivatives (eg vitamin E acetate), vitamin A and derivatives (eg vitamin A palmitate) and also benzoin resin coniferyl benzoate, acid rutinic and derivatives thereof, glycosylrutin, ferrulic acid, furfurylidene glucitol, carnosine, hydroxytoluene butyl, hydroxyanisol butyl, nordihydroguaiaretic acid, trihydroxybutyrophenone, uric acid and derivatives thereof, mannose and derivatives thereof, superoxide dismutase, N- [3 (3,5-di-tert-butyl-4-hydroxy-phenyl) propionyl] sulfanilic acid (and salts thereof, for example, the disodium salts), zinc and derivatives of them (for example, ZnO, ZnSO ₄ ), selenium and derivatives thereof (for example, methionine selenium), stilbene and derivatives thereof (for example, stilbene oxide, trans-stilbene oxide) and the appropriate derivatives according to invention (salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids) of those active ingredients mentioned. HALS compounds (= Impeded Amine Light Stabilizers ”) can also be mentioned. The amount of antioxidants present is generally from 0.001 to 30% by weight, preferably from 0.01 to 3% by weight, based on the weight of the UV absorber of formula (1).

Hydrotropic Agents

To improve the flow behavior, it is also possible to employ hydrotropic agents, for example, ethoxylated and non-ethoxylated monoalcoholes, diols or polyols with a low number of carbon atoms or their ethers (eg ethanol, isopropanol, 1,2-dipropanediol, propylene glycol, glycerin, ethylene glycol, ethylene glycol monoethylether, ethylene glycol monobutylether, propylene glycol monomethylether, propylene glycol monoethylether • ·· • ·· ··· • · · • · · · · ··· • · ·

col, propylene glycol monobutylether, diethylene glycol monomethylether; diethylene glycol monoethylether, diethylene glycol monobutyleter, and similar products). The polyols that are taken into account for that purpose preferably have 2 to 15 carbon atoms and at least two hydroxy groups. Polyols can also contain additional functional groups, especially amino groups and / or can be modified with nitrogen. Typical examples are as follows: glycerol, alkylene glycols, for example, ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol and also polyethylene glycols having an average molecular weight of about 100 to 1,000 Dalton; technical oligoglycerol mixtures having an intrinsic degree of condensation of 1.5 to 10, for example, technical diglycerol mixtures having a diglycerol content of 40 to 50% by weight; methylol compounds, such as, especially, trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol; alkyl glycosides, especially those having 1 to 8 carbon atoms in the alkyl radical, for example, methyl and butyl glycoside; sugar alcohols having 5 to 12 carbon atoms, for example, sorbitol or mannitol; sugars having 5 to 12 carbon atoms, for example, glucose or sucrose; amino sugars, for example, glucamine; di-alcohol amines, such as, diethanolamine or 2-amino-1,3-propanediol.

Preservatives and bacteria-inhibiting agents

Suitable preservatives include, for example, methyl, ethyl, propyl-parabens, benzalkonium chloride, 2-bromo-2-nitro-propane-1,3-diol, dehydroacetic acid, urea diazolidine, 2-dichloro-benzyl alcohol, idantoin DMDM , formic aldehyde solution, methyldibromoglutanitrile, phenoxyethanol, sodium hydroxymethylglycinate, imidazolidinyl urea, triclosan and additional substance classes listed in the following reference: KF DePolo - A short textbook of cosmetology, chapter 7, Table 7-2, 7-3, 7-4 and 7-5, pages 210-219.

Bacterial inhibiting agents

Typical examples of bacteria-inhibiting agents are preservatives that have a specific action against gram-positive bacteria,

such as 2,4,4'-trichloro-2'-hydroxydiphenyl ether, chlorhexidine (1,6-di (4-chlorophenyl-biguanide) hexane) or TCC (3,4,4'-trichlorocarbanylide). A large number of aromatic substances and ethereal oils also have antimicrobial properties. Typical examples are the active ingredients eugenol, menthol and thymol in clove oil, peppermint oil and thyme oil. A natural deodorizing agent of interest is farnesol alcohol terpene (3,7,11-trimethyl-2,6,10-dodecatrien-1-ol), which is present in lime flower oil. Glycerol monolaurate has also proven to be a bacteriostatic agent. The amount of additional bacterial inhibiting agents present is generally 0.1 to 2% by weight, based on the solids content of the preparations.

Scented oils

They can be mentioned as scented oils, mixtures of natural and / or synthetic aromatic substances. Natural aromatic substances are, for example, flower extracts (lilac, lavender, roses, jasmine, nerole, ilang-ilang) from stems and leaves (geranium, patchouli, petitgrain), fruits (anise seed, coriander, carraway, junipero), fruit peels (bergamot, lemons, oranges), roots (mace, angelica, celery, cardamon, cane-marsh, iris, calmus), wood (pine, sandalwood, guaiacum, cedar, rose wood ), ivy and grass (tarragon, lemongrass, sage, thyme), stems and sprouts (spruce, pine, Scottish pine, mountain pine), resins and balms (galbanum, elemi, benzoin, myrrh, oliban, opoponax ). Raw materials from animals are also taken into account, for example, musk and castoro. Typical synthetic aromatic substances are, for example, ester, ether, aldehyde, ketone, alcohol or hydrocarbon type products. Ester-type aromatic compounds are, for example, benzyl acetate, phenoxyethyl isobutyrate, pterc-butylcyclohexyl acetate, linaloyl acetate, dimethylbenzylcarbinyl acetate, phenylethyl acetate, linalyl benzoate, benzyl formate, ethylionyl ethylene glycate, allylethylphenyl glycate, styryl propionate and benzyl salicylate. Ethers include, for example, benzyl ethyl ether; aldehydes include, for example, the linear alkanes of 8 to 18 hydrocarbon atoms, citral, • · • ·· · * · citronellal, citronellyl oxyacetaldehyde, cyclamen aldehyde, hydroxycitonelal, lilial and bourgeonal; ketones include, for example, ionones, isomethionone and methyl cedril ketone; alcohols include, for example, anethole, citronelol, eugenol, isoeugenol, geraniol, linalool, phenyl ethyl alcohol and terpinol; and hydrocarbons mainly include terpenes and balms. However, it is preferable to use mixtures of various aromatic substances which together produce a pleasant smell. Ethereal oils of relatively low volatility, which are mainly used as aroma components are also suitable as perfumed oils, for example, sage oil, chamomile oil, clove oil, melissa oil, cinnamon leaf oil, flower oil lime, juniper berry oil, vetiver oil, oliban oil, galbanum oil, labolanum oil and lavender oil. Preference is given to the use of bergamot oil, dihydromyrcenol, lilac, liral, citronelol, phenyl ethyl alcohol, hexyl cinnamaldehyde, geraniol, benzyl acetone, cyclamen aldehyde, linalool, boisambrene forte, ambroxan, indole, hedione, sandelice, lemon oil , tangerine oil, orange oil, allyl amyl glycolate, cyclovertal, lavender oil, muscat sage oil, damascone, bourbon geranium oil, cyclohexyl salicylate, vertofix coeur, iso-E Super, Fixolide NP, evernyl, iraldein gamma, phenylacetic acid, geranyl acetate, benzyl acetate, rose oxide, romillat, irotil and floramat alone or in a mixture.

Dyes

Substances that are suitable and permitted for cosmetic purposes can be used as dyes, as compiled, for example, in the publication Kosmetische Fãrbemittel de Farbstoffkommission der Deutschen Forschungsgemeinschaft, Verlag Chemie, Weinheim, 1984, pages 81 to 106. Dyes are generally used in concentrations of 0.001 to 0.1% by weight, based on the total mixture.

Other adjuvants

It is possible, in addition, that cosmetic preparations contain, as adjuvants, defoamers, such as, silicones, structurizers, such as maleic acid, solubilizers, such as ethylene glycol,

• · · · ······ • · · · propylene glycol, glycerol or diethylene glycol, opacifiers such as latex, styrene / PVP or styrene / acrylamide copolymers, complexing agents such as EDTA, NTÂ, alaninadiacetic acid or phosphonic acids, propellants, such as propane / butane mixtures, N2O, dimethyl ether, OC ₂ , N ₂ or air, components called so-called couplers and descriptors, such as oxidation dye precursors, reducing agents such as thioglycolic acid and derivatives thereof, thiolactic acid, cysteamine, thiomolic acid or mercaptoethanesulfonic acid or oxidizing agents such as hydrogen peroxide, potassium bromate or sodium bromate.

Suitable insect repellents are, for example, N, N-diethylm-toluamide, 1,2-pentanediol or 3535 insect repellents; suitable self-tanning agents, for example, dihydroxyacetone and / or erythrulose or dihydroxy acetone and / or dihydroxy acetone precursors, as described in WO 01/85124 and / or erythrulose.

Polymer beads or hollow spheres as SPF enhancers

The combination of UV absorbers and combinations of UV absorbers, listed above with SPF enhancers, such as non-active ingredients such as styrene / acrylate copolymer, silica beads, spheroidal magnesium silicate, cross-linked Polymethylmethacrylates (PMMA; Micopearl M305 Seppic) , can better maximize the UV protection of sun products. Holosphere additives (Sunspheres® ISP, Silica Shells Kobo.) Deflect radiation and the photon passage length is therefore improved. (EP0893119). Some beads, as mentioned earlier, provide a feeling of softness during spreading. In addition, the optical activity of such beads, for example, Micropearl M305, can modulate the brightness of the skin eliminating the phenomenon of reflection and indirectly can diffuse UV light. When formulated in oil / water emulsions, the preferred amount of such SPF enhancers would represent 1% to 10% of the total amount of the emulsion.

Cosmetic and pharmaceutical preparations

Cosmetic and pharmaceutical formulations are contained in a wide variety of cosmetic preparations. They are taken into account • ·· ··· • · • · · ·· • · · · · ········ ········ »• · · · · · · • · · · Feed, for example, the following preparations:

- skin care preparations, for example, skin washing and cleaning preparations in the form of tablets or liquid soaps, soap-free detergents or washing pastes,

- bath preparations, for example, liquids (bubble baths, milks, bath preparations) or solid bath preparations, for example, bath cubes and bath salts;

- skin care preparations, for example, skin emulsions, multiple emulsions or skin oils;

- cosmetic preparations for personal care, for example, facial makeup in the form of day creams or powder creams, face powder (loose or pressed), blusher or creamy makeup, eye care preparations, for example, eye shadow preparations, masks, eyeliner, eye creams or eye creams, lip care preparations, for example, lipsticks, sparkles, lip contour pencils, nail care preparations such as nail polish, nail polish remover, nail hardeners or cuticle removers;

- foot care preparations, for example, foot baths, foot powders, foot creams or balms, special deodorants and antiperspirants or heat removal preparations;

- preparations for protection from light, such as milks for sun exposure, lotions, creams or oils, sunscreens or tropical, pre-sun or after-sun preparations;

- preparations for tanning the skin, for example, self-tanning creams;

- depigmentation preparations, for example, skin lightening preparations or skin lightening preparations;

- insect repellents, for example, insect repellent oils, lotions, sprays or sticks;

- deodorants, such as spray deodorants, bomb sprays, deodorant gels, sticks or roll-nos;

- antiperspirants, for example, antiperspirant sticks,

· ♦ • · month or roll-us;

- preparations for cleaning and caring for stained skins, for example, synthetic detergents (solids or liquids), preparations for peeling or abrasion or masks for peeling;

- chemical hair removal preparations (depilation), for example, hair removal powders, liquid hair removal preparations, hair removal cream or paste preparations, gel hair removal preparations or aerosol foams ;

- shaving preparations, for example, shaving soap, foaming shaving creams, non-foaming shaving creams, foams and gels, pre-shaving preparations for dry shaving, aftershave or aftershave lotions;

- fragrance preparations, for example, fragrances (toilet water, toilet water, scented water, toilet scents, perfumes), scented oils or scented creams;

- cosmetic preparations for hair treatment, for example, hair washing preparations in the form of shampoos and conditioners, hair care preparations, for example, pre-treatment preparations, hair tonics, styling creams, styling gels, ointments, rinse creams, treatment packages, intensive hair treatments, preparations for capillary structuring, for example, preparations for curling hair for permanent waves (hot, mild or cold curling), preparations for straightening hair, liquid preparations for fixing hair hair foams, hair sprays, whitening preparations, for example, hydrogen peroxide solutions, softening shampoos, bleaching creams, bleaching powders, bleaching pastes or oils, temporary, semi-temporary or permanent hair dyes, preparations containing self- oxidation or natural hair dyes, such as henna and chamomile.

Presentation forms

The final formulations listed can exist in a wide variety of presentation forms, for example:

• ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ ・

♦ · • «·» • «

- in the form of liquid preparations, such as water / oil, oil / water, oil / water / oil, water / oil / water or PIT emulsion and all types of microemulsions,

- in the form of a gel,

- in the form of an oil, cream, milk or lotion,

- in the form of a powder, hairspray, tablet or makeup,

- in the form of a stick,

- in the form of a spray (gas spray or pump spray) or an aerosol,

- in the form of a foam or

- in the form of a paste.

Particularly important as cosmetic preparations for the skin are light protection preparations, such as milks for use in the sun, creams, oils, sunscreens or tropicals, pre-sun preparations or after-sun preparations, also preparations for tanning the skin. skin, for example, self-tanning creams. Of particular interest are sun protection creams, sun protection lotions, sun protection milks and sun protection preparations in the form of a spray.

The aforementioned preparations for hair treatment are of particular importance as cosmetic hair preparations, especially hair washing preparations, in the form of shampoos, hair conditioners, hair care preparations, for example, pre-treatment preparations , hair tonics, styling creams, styling gels, ointments, rinse creams, treatment packages, intensive hair treatments, hair straightening preparations, hair styling preparations, foams and hair sprays. Of special interest are the preparations for washing hair, in the form of shampoos.

A shampoo has, for example, the following composition: from 0.01 to 5% by weight of a UV absorber according to the invention, 12.0% by weight of lauret-2-sulfate, 4.0% by weight of cocoamidopropyl betaine, 3.0% by weight of sodium chloride and addition of water to 100%.

For example, the following cosmetic formulations for hair can be used in particular:

a-ι) spontaneous emulsifying stock formulation, consisting of the UV absorber according to the invention, PEG-6-C-10 oxoalcohol and sorbitan sesquioleate to which water and any desired quaternary ammonium compound, for example, chloride amidopropyl dimethyl-2-hydroxyethylammonium of 4% vision or Quaternium 80, a ₂ ) formulation of spontaneous emulsifying stock, consisting of the UV absorber according to the invention, tributyl citrate and PEG20 sorbitan monooleate, to which water and any desired quaternary ammonium compound, for example, 4% vision amidopropyl dimethyl-2-hydroxyethylammonium chloride or Quaternium 80,

b) solutions doped with quat of the UV absorber according to the invention in butyl triglycol and tributyl citrate;

c) mixtures or UV absorber solutions according to the invention with n-alkylpyrrolidone.

Other typical ingredients of such formulations are preservatives, bactericides and bacteriostatic agents, perfumes, dyes, pigments, thickening agents, wetting agents, fats, oils, waxes, or other ingredients of personal care and cosmetic formulations, such as, alcohols, polyalcohols, polymers, electrolytes, organic solvents, silicon derivatives, emollients, emulsifiers or emulsifying surfactants, dispersing agents, antioxidants, anti-irritants and anti-inflammatory agents, etc.

Examples of cosmetic and pharmaceutical preparations (X = preferred combinations)

Oil-water systems • · ··· · · · · · ········ • · ··· · · · · · · · · · · · · · ··· ··· • · • ··

Ingredients 1 2 3 4 5 6 7 8 Emulsifiers Cetyl potassium phosphate 2% -5% X Cetearyl alcohol / Dicetyl phosphate / Cetet-10 Phosphate 2% -6% X Stearyl Sodium Phtalamate 1% -2% X Cetearyl alcohol / Behentrimony methosulfate 1% -5% X Quaternium-32 1% -5% X Copolyol dimethicone / Caprylic triglyceride / capric 1% -4% X Estearet-2 / Estearet-21 2% -5% X Polyglyceryl methyl glucose distearate 1% -4% X Lipophilic emollient / oil dispersant 15% -20% X X X X X X X X

Fatty alcohols and / or waxes 1% -5% X X X X X X X X Thickeners (water-swelling thickeners) 0.5% -1.5% X X X X X X X X Preservatives 0.5% -1% X X X X X X X X Chelating agents (such as EDTA) 0% -0.2% X X X X X X X X Antioxidants 0.05% - 0.2% X X X X X X X X 100% Qs deionized water X X X X X X X X Scented oils 0.1% - 0.4% X X X X X X X X UV absorber according to the invention 1% - 20% X X X X X X X X UV absorber as described in tables 1-3 0% -30% X X X X X X X X

Water-Oil Systems

Ingredients 1 2 3 4 5 Emulsifiers Polyglyceryl-2 Dipolyhydroxystearate 2% -4% X PEG-30 Dipolyhydroxystearate 2% -4% X Rapeseed oil sorbitol esters 1% -5% X PEG-45/1% -5% dodecyl glycol copolymer X Sorbitan oleate / Policerol-3 ricinoleate 1% -5% X Lipophilic emollient / oil dispersant 10% -20% X X X X X Fatty alcohols and / or waxes 10% -15% X X X X X Electrolytes (NaCI, MgSO ₄ ) 0.5% -1% X X X X X Polyol phase (Propylene glycol, glycerin) 1% - 8% X X X X X Preservatives 0.3% - 0.8% X X X X X Scented oils 0.1% - 0.4% X X X X X Chelating agents (such as EDTA) 0% - 0.2% X X X X X Antioxidants 0.05% - 0.2% X X X X X 100% Qs deionized water X X X X X UV absorber according to the invention 1% - 20% X X X X X UV absorber as described in table 1-3 0% - 30% X X X X X

Water / Silicone Systems

Ingredients 1 2 3 4 Emulsifiers Dimethicone copolyol / Cyclomethicone 5% -10% X X Copoliol Laurildimethicone 5% -10% X X Silicone phase Cyclopentassiloxane 15% -25% X X Dimethicone 15% -25% X X Silicone elastomer Cross-polymer Dimethicone / Vinildimethicone 1% -10% X X X X Humectant / polyols (Propylene glycol, glycerin ...) 2% -8% X X X X Gelling agents (such as EDTA) 0% -0.2% X X X X

Ingredients 1 2 3 4 Antioxidants 0.05% -0.2% X X X X Preservatives 0.3% -0.8% X X X X Scented oils 0.1% -0.4% X X X X Deionized water Qs 100% X X X X UV absorber according to the invention 1% -20% X X X X UV absorber as described in table 1 -3 0% -30% X X X X

Multiple emulsions

Ingredients 1 2 3 4 5 6 7 8 9 10 11 12 Primary emulsion Water1 / oil PEG-30 Dipolyhydroxystearate 2% -6% X X X Dimethicone cetyl copolyol 1% -3% X X PEG-30 Dipolyhydroxy- esterate / Estearet-2 / Estearet-21 4% - 6% X X Polyglyceryl-2 Dipolihi- stearate doxy 1% -3% X X Polyglyceryl-6 Ricinoleate 1% -3% X X X Oily phase 15% -30% Fatty acid esters X X X X X X X Natural and synthetic triglycerides X X X X X X X Hydrocarbon oils X X X X X X X Silicone Oils X X X X X X X Preservatives 0.3% - 0.8% X X X X X X X X X X X X Deionized water qs 100% X X X X X X X X X X X X Monofunctional oil-water emulsifiers ionic Sorbitan stearate / Cocoate of sucrose 3% -7% X X X Sucrose laurate 3% -7% X X X Poloxamer 407 3% -7% X X X

Ingredients 1 2 3 4 5 6 7 8 9 10 U 12 Sorbate monoleate polyethylene (20) 3% -5% X X X Primary water / oil emulsion1 50% X X X X X X X X X X X X Thickeners (intact polymers miscible in water) 0.3% -1% X X X X X X X X X X X X 100% Qs deionized water X X X X X X X X X X X X Scented oils 0.1% -0.4% X X X X X X X X X X X X UV absorber according to invention 1% -20% X X X X X X X X X X X X UV absorber as described in table 1-3 0% -30% X X X X X X X X X X X X

Emulsions Oil1 / Water / Qleo2

Ingredients 1 2 3 4 5 6 7 8 Primary Emulsion Oil1 / Water PEG-60 Hydrogenated castor oil 25% X X X X Estearet-25 25% X X X X Oily phase 75% Fatty acid esters X X Natural and synthetic triglycerides X X Hydrocarbon oils X X Silicone Oils X X Preservatives 0.3% -0.8% X X X X X X X X 100% Qs deionized water X X X X X X X X Non-multifunctional water-oil emulsifier ionic 2% -5% X X X X X X X X Waxes 1% -5% X X X X X X X X Oily phase 20% -30% X X X X X X X X

Ingredients 1 2 3 4 5 6 7 8 Fatty acid esters Natural and synthetic triglycerides Hydrocarbon oils Silicone Oils Primary Oil-in-Water Emulsion 15% X X X X X X X X Electrolytes (NaCl, M ₂ SO ₄ ) 0.1% -0.5% X X X X X X X X 100% Qs deionized water X X X X X X X X Scented oils 0.1% -0.4% X X X X X X X X UV absorber according to the invention 1% -20% X X X X X X X X UV absorber as described in tables 1-3 0% -30% X X X X X X X X

Microemulsions

Ingredients 1 2 3 4 5 6 7 8 9 10 Surfactants PEG-8 Caprylic / capric glycerides 10% - 25% X X X X X PPG-5-cetet-20 10% -25% X X X X X Cotensoactives Polyglyceryl-6 isostearate 5% -15% X X Polyglyceryl-3 diisoestearate 5% -15% X X Polyglyceryl-6 dioleate 5% -15% X X PPG-10 cetyl ether 5% -15% X X Etoxidiglycol 5% -15% X X Oily phase 10% -80% X X X X X X X X X X Isostearyl benzoate Isostearyl isostearate PEG-7 Glyceryl cocoate Cyclomethicone

Ingredients 1 2 3 4 5 6 7 8 9 10 Polyalcohols / Humectants 1% -10% X X X X X X X X X X Preservatives 0.3-0.8% X X X X X X X X X X Scented oils 0.1% -0.4% X X X X X X X X X X Deionized water qs 100% X X X X X X X X X X UV absorber according to the invention 1% -20% X X X X X X X X X X UV absorber as described in tables 1-3 0% -30% X X X X X X X X X X

Oil-water emulsions

Inoredientes 1 2 3 4 5 6 Emulsifiers 0.1% -5% alkyl phosphates X X X Glycosidic derivatives 0.1% -5% X X X Solubilizers Ethoxylated glyceryl ethers 0.1% -1% X X Polysorbates 0.1% -1% X X Ethoxylated oleyl ethers 0.1% -1% X X Film forming agents PVP / VA copolymer 1% -10% X X X PVM / MA copolymer 1% -10% X X X Oily phase 5% -20% X X X X X X Natural oils (Meadowfoam, Jojoba, Macadamia) Fatty acid esters Mineral oils Silicone Oils Alcohol 0% -50% X X X X X X Thickeners 0.1% -0.5% X X X X X X Polyacrylates Aluminum / Magnesium Silicates Gums Neutralizing agents 0% -1% X X X X X X

• · · · ·

Ingredients 1 2 3 4 5 6 Polyalcohols / Humectants 1% -5% X X X X X X Chelating agents (such as EDTA) 0% -0.2% X X X X X X Antioxidants 0.05% -0.2 X X X X X X Deionized water qs 100% X X X X X X Scented oils 0.1% -0.5% X X X X X X Preservatives 0.4% -1% X X x X X X UV absorber according to the invention 1% - 20% X X X X X X UV absorber as described in the tables 1-3 0% - 30% X x X X X X

G-Aqueous

Ingredients 1 2 3 4 5 6 7 8 9 10 11 12 Thickeners Natural thickener 1% -5% X X X X Semi-synthetic thickener 1% -5% X X X X Synthetic thickener 0.3% -1.3% X X X X Neutralizing agents 0.5% -1.5% X X X X X X X X X X X X Polyols - Humectants 5% -50% X X X X X X X X X X X X Training agent film / conditioner Polyquaternium series 1% -5% X X X X X X PVM / MA copolymer 1% -5% X X X X X X Preservatives 0.5% -1% X X X X X X X X X X X X Chelating agents (such as EDTA) <0.1% X X X X X X X X X X X X Deionized water qs 100% X X X X X X X X X X X X Scented oils 0.05% -0.4% X X X X X X X X X X X X Solubilizers Ethyl glyceryl ethers 0.1% -5% X X X Polysorbates 0.1% -5% X X X

Ingredients 1 2 3 4 5 6 7 8 9 10 11 12 Ethoxylated oleyl ethers 0.1% -5% X X X X X X UV absorber according to the invention 1% -20% X X X X X X X X X X X X UV absorber as described in tables 1 -3 0% -30% X X X X X X X X X X X X

Oily gels

Ingredients 1 2 3 4 5 6 7 8 9 10 Thickeners Hydrogenated lecithin 1% -10% X X 1% -10% silica dimethyl silylate X X Silica 1% -5% X X C24-28 Alkyl Dimethicone 1% -5% X X Aluminum or magnesium stearate 1% -5% X X Polyols - Humectants 5% -70% X X X X X X X X X X Oily phase 20% -90% Tipprylic Ether X X X Phenyl trimethicone X X Hydrogenated polyisobutene X Isopropyl isostearate X X Oily gel bases (mineral oil and butylene / ethylene copolymer or ethylene / hydrogenated propylene) X X Silicone wax 1% -10% X X X X X X X X X X Dimethiconol behenate Dimethicone Stearate Scented oils 0.1% -0.5% X X X X X X X X X X Antioxidants 0.05% -0.2% X X X X X X X X X X

Ingredients 1 2 3 4 5 6 7 8 9 10 UV absorber according to invention 1% -20% X X X X X X X X X X UV absorber as described in tables 1-3 0% -30% X X X X X X X X X X

Dry / light-protecting cosmetic oils

Ingredients 1 2 3 4 Lipophilic base Hydrocarbon oils 30% -70% X X Branched or non-branched fatty acid esters 10% -50% X X Light sensitive patient Silicones / Siloxanes 0% -10% X X Perfluorinated oils and perfluorethers 0% -10% X X Viscosity agents 0% -10% X X X X Waxes Esters of long chain acids and alcohols 0% -2% X X X X Antioxidants 0, 1% -1% X X X X Solubilizing / dispersing agents 0% -5% X X X X Scented oils 0.1% -0.5% X X X X UV absorber according to the invention 1% -20% X X X X UV absorber as described in tables 1-3 0% -30% X X X X

• ··· ·· ·

Foaming / mousse products

Ingredients SD 40 Alcohol 0% -8% X Propellant 8% -15% X Emulsifier / nonionic surfactant 0.5% - 3% X Corrosion inhibitor 0% -1% X Scented oils 0.1% -0.5% X Preservatives 0.1% -1% X Miscellaneous 0% -1% X UV absorber according to the invention 1% -20% X UV absorber as described in tables 1-3 0% -30% X

Stick products

Ingredients Waxes 15% -30% X Natural and silicone oils 20% -75% X Lanolin derivatives 5% -> 50% X Lanolin esters X Acetylated lanolin X Lanolin oil X Dyes and pigments 10% -15% X Antioxidants 0.1% - 0.8% X Scented oils 0.1% - 2% X Preservatives 0.1% -0.7% X UV absorber according to the invention 1% -20% X UV absorber as described in tables 1-3 0% -30% X

• ·· ···

Liquid and Compact

Ingredients 1 2 Liquid base Powder phase 10% -15% X Oily phase 30% -40%; 75% (only for anhydrous form) X Thickeners / suspension 1% -5% x Film-forming polymers 1% -2% X Antioxidants 0.1% -1% x Scented oils 0.1% - 0.5% x Preservatives 0.1% -0.8% x 100% Qs deionized water x Compact Powder Powder phase 15% -50% X Oily phase 15% - 50% X Polyol phase 5% -15% X Antioxidants 0.1% -1% x Scented oils 0.1% - 0.5% x Preservatives 0.1% -0.8% X For both product forms UV absorber according to the invention 1% -20% x x UV absorber as described in tables 1-3 0% -30% x X

Conditioning shampoos

Ingredients 1 Primary surfactants (listed above) 5% -10% X Secondary surfactants (listed above) 5% -15% X Foam stabilizers (previously listed) 0% -5% X Deionized water 40% -70% x Active 0-10% X Conditioners X Re-greasing agents X Wetting agents X Thickeners / rheology modifiers 0% -3% X Humectants 0% -2% X

Ingredients 1 PH adjustment agents 0% -1% X Preservatives 0.05% -1% X Scented oils 0.1% -1% X Antioxidants 0.05% -0.20% X Gelling agents (EDTA) 0% -0.2% X Opacifying agents 0% -2% X UV absorber according to the invention 1% -20% X UV absorber as described in tables 1-3 0% -30% X

The cosmetic preparation according to the invention is distinguished by the excellent protection of human skin against the harmful effect of the sun.

In the examples that follow, the percentages refer to weight and the temperature is given at ⁰ Celsius.

Examples

Example 1: Preparation of the compound of the formula

A mixture consisting of 6.4 g of 4-aminobenzene acid ethyl ester (0.025 mol), 8.7 g of N, N-dimethyl-acetamide (0.0527) and 20 ml of dioxane (0.23 mol) is added dropwise drop to a solution of 6.4 g 10 of 2,4-dichloro-6- (4-methoxyphenyl) - [1,3,5] -triazine (0.025 mol) in 80 ml of dioxane (0.92 ). The reaction solution was stirred for 4 ½ hours at 80 ° C. After that 100 ml of water (0.18 mol) are added slowly. The reaction product is filtered at 20 ° C and washed with dioxane and water. The reaction is also recrystallized from dimethylformamide boiled in methanol.

The product obtained is dried in vacuo. The yield of the white product is 4.2 g (32.7%).

Example 2:

Analogous to Example 1 the compound of the formula:

(102)

is obtained if, 4-aminobenzoic ester (2-ethylhexyl) is used instead of 4-aminobenzene acid ethyl ester.

Example 3:

Analogous to Example 1 the compound of the formula:

(103)

is obtained, if 4-aminobenzoic acid methyl ester is used instead of 4-aminobenzoic acid ethyl ester.

Example 4:

Analogous to Example 1 the compound of the formula:

is obtained if 4-aminobenzoic acid is used instead of 4-aminobenzoic acid ethyl ester.

• •• tftftftf · · • tf ··· · «···· * tftf · \ • · \

Example 5:

Analogous to Example 1 the compound of the formula:

(105)

NH, is obtained if 4-amino benzoic acid amide is used instead of 4-aminobenzoic acid ethyl ester.

Example 6:

100 parts of the compound of the formula:

(106)

They are ground together with grinding aids, for example, consisting of zirconium silicate (diameter of the beads: 0.1 to 4 mm), a dispersing agent (15 parts of polyglycoside alkyl) and water (85 parts) in one ball mill until a micropigment is obtained with an average particle size of dso = 200 nm.

A micropigment dispersion of the UV absorber is thus obtained.

• · • ·· • ··· • · • ·· • · · • · · · ······

Application Examples

Example 7: UV protection lotion for daily use UV-A / UV-B

Composition First name INCI % weight / weight (as supplied) 5 Part A Olet-3 Phosphate 0.60 Estearet-21 2.50 Estearet-2 1.00 Cetyl alcohol 0.80 Stearyl alcohol 1.50 10 Tribehenina 0.80 Isohexadecane 8.00 Ethylexyl methoxycinnamate 5.00 Part B Water qs to 100 Glycerin 2.00 15 Dispersion of UV absorber according to prepared in Example 6 3.00 Disodium EDTA 0.10 Part C Water 20.00 Diazolidinyl urea (e) butylcarbamate of 20 iodopropynil 0.15 Propylene glycol 4.00 Part D Sodium acrylate copolymer (e) Paraffin (e) PPG-1 Tridecet-6 1.50 Cyclopentasiloxane 4.50 25 PEG-12 dimethicone 2.00 Tocopheryl acetate 0.45 Water (e) citric acid what Part E Fragrance what

Preparation

Part A and part B are heated separately to 75 ° C. Part A is poured into part B with continuous agitation. Immediately after emulsification, cyclopentassiloxane and part D PEG-12 dimethicone are incorporated

the mixture. After that, the mixture is homogenized with an Ultra Turrax at 11,000 rpm for 30 seconds and is cooled below 65 ° C and sodium acrylate (e) liquid paraffin (e) PPG-1 Tridecet-6 copolymer is incorporated. Part C is added at a temperature <50 ° C. At 35 ° C or below, tocopheryl acetate is incorporated and subsequently the pH is adjusted with citric acid solution. Part E is added at room temperature.

Example 8: Daily UV Lotion

Composition First name INCI % weight / weight 10 (as supplied) Part A Cetyl phosphate 1.75 C12-C15 alkyl benzoate 5.00 Cetearyl alcohol / PEG-20 stearate 2.00 Ethoxydiglycol oleate 2.00 15 Stearic acid 1.50 Ethylexyl methoxycinnamate 3.00 Isononyl isononanoate 2.00 Part B Water qs to 100 Xanthan gum 0.35 20 Dispersion of UV absorber according to prepared in Example 6 5.00 Disodium EDTA 0.20 Propylene glycol Diazolidinyl urea (e) methylparaben (e) 2.00 25 propylparaben (e) propylene glycol 0.70 Glycerin 1.50 Part C Cyclopentassiloxane (e) dimethicone 1.00 Etoxidiglycol 3.00 Dimethicone 2.00 30 Part D Triethanolamine what

Preparation

Part A is prepared by incorporating all the ingredients, then stirred at moderate speed and heated to 75 ° C. Part B is prepared and heated to 75 ° C. At this temperature, part B is poured into part A under progressive stirring speed, then homogenized (30 seconds, 15000 rpm). Below 55 ° C, the ingredients of part C are incorporated. After cooling under moderate stirring, the pH is checked and adjusted with triethanolamine. Example 9: Emulsion for Sun Protection

Composition First name INCI % weight / weight 10 Part A Cetearyl alcohol (e) phosphate (as supplied) dicetyl (e) cetet-10 Phosphate 4.00 C12-15 alkyl benzoate 2.00 Tipprylic Ether 3.00 15 Ethoxydiglycol oleate 2.00 Stearic acid 1.00 Ethylexyl methoxycinnamate 3.00 Sodium acrylate (e) glycine copolymer soy (e) PPG-1 tridecet-6 0.30 20 Squalane 3.50 Part B Water qs to 100 UV absorber dispersion as prepared in Example 6 5.00 Part C Diazolidinyl urea (e) butylcarbamate of 25 iodopropynil 0.15 Propylene glycol 2.50 Water 10.00 Part D Cyclopentassiloxane, dimethicone 2.00 Etoxidiglycol 5.00 30 Cyclopentassiloxane (e) dimethicone / vinyl-dimethicone Cross polymer 2.00 Part E Sodium hydroxide 0.10

Preparation

Part A is prepared by incorporating all the ingredients, then stirred at moderate speed and heated to 75 ° C. Part B is prepared and heated to 75 ° C. At this temperature, part B is poured into part A under progressive agitation speed. Below 65 ° C, the ingredients of part D are incorporated separately. After cooling under moderate stirring to 55 ° C, part C is added. The pH is checked and adjusted with sodium hydroxide. The formulation is homogenized for 30 seconds at 16,000 rpm.

Example 10: Daily use lotion

Composition First name INCI % weight / weight (as supplied) Part A Stearyl phosphate 5.00 Tricontanil PVP 1.00 15 Ethoxydiglycol oleate 3.00 Squalane 5.00 C12-15 alkyl benzoate 5.00 Ethylexyl methoxycinnamate 3.00 Glyceryl stearate 2.00 20 Cetyl alcohol 2.00 Part B Water 20.00

Dispersion of UV absorber according to

Part C prepared in Example 6 Water 3.00 qs to 100 25 Estearet-10 allyl ether / acrylates copolymer 0.50 Glycerin 2.50 Diazodinyl urea (e) butylcarbamate of iodopropynil 0.15 Sodium lauroyl glutamate 0.70 30 Part D Cyclopentassiloxane (e) dimethicone 1.50 Triethanolamine 1.85

Preparation

Part A is prepared by incorporating all the ingredients, then stirred at moderate speed and heated to 75 ° C. Part C is prepared and heated to 75 ° C. Part C is poured into part A with moderate agitation. Immediately after emulsification, part B is added, then neutralized with a part of triethanolamine. The formulation is homogenized for 30 seconds. After cooling under moderate stirring, cyclopentasiloxane (e) dimethicone is added. Below 35 ° C the pH is checked and adjusted with triethanolamine.

Example 11: Sunscreen spray emulsion

Composition Name INCI% weight / weight (as supplied)

Part A

Part B

Part C

Cetearet-15 (e) glyceryl stearate 3.00 Stearyl alcohol 1.00 Cetyl ricinoleate 0.80 Tipprylic Ether 3.00 C12-15 alkyl benzoate 3.00 Isoexadecane 2.50 Stearyl dimethicone 1.00 Ethylexyl methoxycinnamate 4.00 Cetyl alcohol 0.80 DÍ-C12-13 alkyl tartrate 3.00 Water qs to 100 Estearet-10 allyl ether / acrylates copolymer 0.45 PEG-7 glyceryl cocoate 2.50 Glycerin 2.00 Propylene glycol 3.00 Diazolidinyl urea (e) butylcarbamate of iodopropynil 0.15 Water 20.00 Dispersion of UV absorber according to prepared in Example 6 12.00

Titanium dioxide (e) silica (e) sodium polyacrylate

Cyclopentassiloxane (e) dimethiconol Sodium hydroxide (e) water Fragrance

8.00

0.85 qs for pH 6.50-7.00 qs

Part D Part E Part F Preparation

Part A and part B are heated to 80 ° C. Part A is combined in part B with agitation and homogenized with an Ultra Turrax at 11,000 rpm for 30 seconds. Part C is heated to 60 ° C and the emulsion is added slowly. After cooling to 40 ° C, part D is incorporated. Parts E and F are added at room temperature.

Example 12: Daily care lotion

Composition Name INCI% weight / weight (as supplied)

Part A

Part B

Polyglyceryl methyl glucose distearate 2.50

Cetearyl alcohol 2.00

Octyl stearate 3.00

Caprylic triglyceride / capric 4.00

Isoexadecane 4.00

Ethylexyl methoxycinnamate 2.70

Water 64.80

Glycerin 5.00

Phenoxyethanol (e) methylparaben (e) butylparaben (e) ethylparaben (e) propylparaben 0.50

UV absorber dispersion as prepared in Example 6 8.00

Part C Cyclomethicone (e) Dimethicone 3.00

Part D Estearet-10 allyl ether / acrylates 0.50 copolymer

Preparation

Parts A and B are heated to 75 ° C. Part A is added to part B with continuous stirring and homogenized at 11,000 rpm for one minute.

After cooling to 50 ° C, part C is added under continuous stirring. After cooling to below 30 ° C, part D is added. After that, the pH is adjusted between 6.00-6.50. Example 13: Daily care with UV protection Composition First name INCI % weight / weight Part A Glyceryl stearate SE Glyceryl stearate and stearate (as supplied) 3.00 PEG-100 3.50 Cetyl alcohol 1.50 Myristyl myristate 2.00 Isopropyl palmitate 2.50 Liquid paraffin 5.00 Dimethyl octyl PABA 3.00 Part B Water qs to 100 Propylene glycol Phenoxyethanol (e) methylparaben (e) butylparaben (e) ethylparaben (e) 7.50 propylparaben 1.00 Part C Water 30.00

UV absorber dispersion as prepared in Example 6 10.00

Part D Sodium acrylate copolymer (e) liquid paraffin (e) PPG-1 tridecet-6 2.00 Part E Citric acid 0.30 Preparation

Parts A and B are heated separately to 75 ° C. after adding part B to part A, the mixture is homogenized with Ultra Turrax for one minute at 11,000 rpm. After cooling to 50 ° C, part C is added. After that, the formulation is homogenized for one minute at 16,000 rpm. Below 40 ° C part D is added. At room temperature the pH value is adjusted with part E between 6.00 and 6.50.

······ «· · • · ··· · · j * 9 · ·

Example 14: Lotion for daily protection against oil-water UV

Composition Name INCI% weight / weight (as supplied)

Part A Glyceryl stearate (e) PEG-100 stearate 5.00 5 Stearyl alcohol 1.00 Tripalmitina 0.70 Dimethicone 2.00 C12-15 alkyl benzoate 5.00 Isopropyl palmitate 5.00 10 Ethylexyl methoxycinnamate 3.00 Part B Water qs to 100 Poiissorbato 60 0.50 Glycerin 3.00 Part C Water 10.00 15 Dispersion of UV absorber according to prepared in Example 6 8.00 Part D Phenoxyethanol (e) methylparaben (e) ethylparaben (e) butylparaben (e) propylparaben (e) isobutylparaben 0.70 20 Estearet-10 allyl ether / acrylates copolymer 1.50 Part E Water (e) sodium hydroxide what Part F Fragrance what Preparation

Parts A and B are heated separately to 75 ° C, part C to 60 ° C. After that, part B is poured into part A with stirring. The mixture is homogenized with an Ultra Turrax for 30 seconds at 11,000 rpm and part C is incorporated. After cooling to 40 ° C, part D is added. At room temperature the pH value is adjusted with sodium hydroxide between

6.30 and 6.70 and part F is added.

ί

Example 15: Daily protection against oil-water UV

Composition Name INCI% weight / weight (as supplied)

Part A Glyceryl stearate (e) PEG-100 stearate 5.00 Stearyl alcohol 1.00 Tripalmitina 0.70 Dimethicone 2.00 C12-15 alkyl benzoate 5.00 Isopropyl palmitate 5.00 Ethylexyl methoxycinnamate 3.00 Part B Water qs to 100 Polysorbate 60 0.50 Glycerin 3.00 Part C Water 10.00 Dispersion of UV absorber according to prepared in Example 6 8.00 Part D Phenoxyethanol (e) methylparaben (e) ethylparaben (e) butylparaben (e) propylparaben (e) isobutylparaben 0.70 Estearet-10 allyl ether / acrylates copolymer 1.50 Part E Water (e) sodium hydroxide what Part F Fragrance what Preparation

Parts A and B are heated separately to 75 ° C, part C to 60 ° C. After that, part B is poured into part A with stirring. After homogenization with an Ultra Turrax for 30 seconds at 11,000 rpm, part C is incorporated. After cooling to 40 ° G, part D is added. At room temperature the pH value is adjusted with sodium hydroxide between 6.30 and 6.70 and part F is added.

Example 16: Sunblock cream

Composition Name INCI

Part A Cetearyl alcohol (e) Dicetyl phosphate (e) 5 Cetet-10 phosphate

C12-15 alkyl benzoate Caprylic / capric triglyceride Pentaerythritol tetraisoestearate Ethylexyl methoxycinnamate

Isoamyl P-methoxycinnamate

Part B Water

Glycerin

Propylene glycol

Aluminum magnesium silicate

Part C Estearet-10 allyl ether / acrylates copolymer UV absorber dispersion as prepared in Example 6

Part D Phenyl trimethicone

Phenoxyethanol (e) methylparaben (e) butylparaben (e) ethylparaben (e) propylparaben

Sodium hydroxide% weight / weight (as supplied)

4.50 6.00 7.00 2.00 3.00 2.00 qs for 100 2.00

1.50 1.20 0.50

12.00

1.50

0.70

0.90

Part And Preparation

Parts A and B are heated separately to 75 ° C. Part B is added to part A under continuous agitation and after that, homogenized with

Ultra Turrax for 30 seconds at 11,000 rpm. After cooling to 60 ° C, part C is added. At 40 ° C, part C is added and homogenized for 15 seconds at 11,000 rpm. At room temperature the pH value is adjusted with part E.

Example 17: Oil / water type UVA / UVB daily care lotion

Composition Name INCI% weight / weight (as supplied)

Part A Glyceryl stearate (e) PEG-100 stearate 5.00

Stearyl alcohol 1.00

Tripalmitin 0.70

Mineral oil 15.00

Part B Water qs for 100

Polysorbate 60 0.50

Glycerin 3.00

Part C Water 10.00

UV absorber dispersion as prepared in Example 6 8.00

Part D Estearet-10 allyl ether / acrylates copolymer 1.50

Phenoxyethanol (e) methylparaben (e) ethylparaben (e) butylparaben (e) propylparaben (e) isobutylparaben Water (e) sodium hydroxide Fragrance

0.70 qs qs

Part E Part F Preparation

Parts A and B are heated separately to 75 ° C, part C to 60 ° C. Part B is poured into part A with agitation. After one minute the mixture is homogenized at 11,000 rpm and part C is added to the A / B mixture. After cooling to 40 ° C, part D is added. At room temperature the pH value is adjusted with part E between 6.30 and 6.70. At the end, part F is added.

• ·· ·· ·

Example 18: UVA / UVB daily care lotion, oil / water type Composition Name INCI% weight / weight (as supplied)

Part A Olet-3 Phosphate 0.60 5 Estearet-21 2.50 Estearet-2 1.00 Cetyl alcohol 0.80 Stearyl alcohol 1.50 Tribehenina 0.80 10 Isoexadecane 8.00 Part B Water gs to 100 Glycerin 2.00 Disodium EDTA 0.10 Part C Cyclopentasiloxane 4.50 15 Dimethicone PEG-12 2.00 Part D Copolymer sodium acrylate (e) oil mineral (e) Trideçet-6 PPG-1 1.50 Part E Dispersion of UV absorber according to prepared in Example 6 10.00 20 Part F Tocopheryl acetate 0.45 DMDM hydantoin (e) butylcarbamate iodopropynyl (e) water (e) butylene glycol 0.85 Part G Water (e) citric acid what Fragrance what

Preparation

Parts A and B are heated separately at 75 ° C. Part A is poured into part B with agitation. Immediately after emulsification, part C is added to the mixture and neutralized with an Ultra Turrax at 11,000 rpm for 30 seconds. After cooling to 65 ° C, sodium acrylate copolymer (e) mineral oil (e) Tridecet-6 PPG-1 is added. At 50 ° C, part E is added slowly. Part F is incorporated at 35-30 ° C. The pH is adjusted with the G part between 5.5 and 6.5.

• · · · · · ············

Example 19: Daily protective lotion UV-A / UV-B, oil / water

Composition Name INCI

Part A Glyceryl dilaurate Ethylexyl palmitate Cetyl alcohol Glyceryl stearate Lauret-23

Isopropyl palmitate Tribehenina Beeswax Lanolin oil

Part B Water

Propylene glycol

Water (e) titanium dioxide (e) alumina (e) sodium metaphosphate (e) phenoxyethanol (e) sodium methyl paraben

Part C Estearet-10 allyl ether / acrylates copolymer Part D Phenoxyethanol (e) methylparaben (e) butylparaben (e) propylparaben (e) isobutylparaben UV absorber dispersion as prepared in Example 6 Water (e) sodium hydroxide % weight / weight (as supplied)

2.00

6.00

1.00

2.00

1.00

2.00

0.80

1.50

1.00 qs to 100 4.00

4.00

1.00

1.00

8.00 qs

Part And Preparation

Parts A and B are heated separately to 80 ° C. Part A is poured into part B while shaking and homogenized in an Ultra Turrax at 11,000 rpm for 30 seconds. After cooling to 60 ° C, part C is incorporated. At 40 ° C part D is added slowly with continuous stirring. The pH is adjusted with part E between 6.5 and 7.0.

• ··· · ········

Example 20: Sunscreen spray lotion

Composition Name INCI% weight / weight (as supplied)

0.20

7.00

1.50 6.00

2.50

4.50 qs for 100 2.00 4.00

Part A Cetyl potassium phosphate 5 Isoexadecane

VP / eicosene copolymer Di-C-12-13 alkyl tartrate Ethylexyl triazone C12-15 alkyl benzoate 10 Part B Water

Sorbet-30

Sorbitan stearate (e) sucrose cocoate Titanium dioxide (e) alumina (e) silica (e) sodium polyacrylate

Part C Water

UV absorber dispersion as prepared in Example 6

Part D Phenoxyethanol (e) methyl paraben (e) ethyl paraben (e) butyl paraben (e) propyl paraben (e) isobutyl paraben

Water (e) citric acid

2.50

30.00

12.00

0.70 qs

Part And Preparation

Part A and part B are heated separately to 80 ° C, part C to 50 ° C. Part B is poured into part A and homogenized with an Ultra Turrax for 1 minute at 11,000 rpm. After cooling to 50 ° C, part C is added under constant stirring. At 40 ° C, part D is incorporated and homogenized again for 10 seconds at 11,000 rpm. The pH is adjusted with part E.

Example 21: Daily protection lotion against UV oil / water

Composition Name INCI% weight / weight (as supplied)

Part A Glyceryl stearate (e) PEG-100 stearate 5.00 5 Stearyl alcohol 1.00 Tripalmitina 0.70 Dimethicone 2.00 Caprylic / capric triglyceride 5.00 Isopropyl palmitate 5.00 10 Ethylexyl methoxycinnamate 3.00 Part B Water qs to 100 Polysorbate 60 0.50 Glycerin 3.00 Part C Water 10.00 15 dispersion of UV absorber as prepared in Example 6 8.00 Part D Phenoxyethanol (e) Methylparaben (e) Ethylparaben (e) Butylparaben (e) Propylparaben (e) lsobutylparaben 0.70 20 Estearet-10 Allyl / acrylate copolymer 1.50 Part E Water (e) sodium hydroxide what Part F Fragrance what Preparation

Parts A and B are heated separately to 75 ° C; part C at 60 ° C. 25 After that, part B is poured into part A with agitation. The mixture is homogenized with an Ultra Turrax for 30 seconds at 11,000 rpm and the

C is incorporated. After cooling to 40 ° C, part D is added. At room temperature the pH value is adjusted with sodium hydroxide between 6.30 and 6.70 and part F is added.

• * ♦ · • · ····· * ·· · · ·· • ············ *

Example 22: water-resistant sunscreen emulsion

Composition Name INCI% weight / weight (as supplied)

Part A Polyglyceryl-10 pentaestearate (e)

Behenyl alcohol (e) sodium stearoyl lactylate 2.50

VP / Eicosene Copolymer 1.50

Stearyl alcohol 1.50

Squalane 4.00

C ₁₂ benzoate. ₁₅ alkyl 7.50

Octocylene 1.50

Camphor 4-methylbenzylidene 3.00

Ethylexyl methoxycinnamate 2.00

Part B Water qs for 100

Glycerin 1.80

Estearet-10 Allyl ether / acrylate 0.80 copolymer

Part C Dispersion of UV absorber as prepared in Example 6 9.00

Part D Copolymer VP / Hexadecene 2.70

Cyclomethicone 1.50

Phenoxyethanol (e) Methylparaben (e)

Ethylparaben (e) Butylparaben (e)

Propylparaben (e) Isobutylparaben 0.70

Part E Water (e) Tocopheryl acetate (e) caprylic / capric triglyceride (e) polysorbate 80 (e) Lecithin 3.50

Part F Fragrance qs

Water (e) sodium hydroxide qs

Preparation

Parts A and B are heated separately to 80 ° C. Part A is poured into part B with continuous agitation. After that, the mixture is homogenized with an Ultra Turrax at 11,000 rpm for 1 minute. After cooling to 60 ° C, part C is incorporated. At 40 ° C part D is added, and homogenized again for a short period of time. At 35 ° C part E is added. Fragrance is added at room temperature. Finally, the pH is adjusted with sodium hydroxide.

Example 23: Sun protection lotion against UVA / UVB, oil / water type

Composition Name INCI

Part A Cetyl potassium phosphate Tricontanil PVP Caprylic / capric triglyceride C12-15 alkyl benzoate Cetearyl isononanoate Glyceryl stearate Cetyl alcohol Dimethicone

Ethylexyl methoxycinnamate

Part B Water

Glycerin

Part C Estearet-10 Allyl / acrylate copolymer

Part D UV absorber dispersion as prepared in Example 6

Part E Phenoxyethanol (e) Methylparaben (e) Ethylparaben (e) Butylparaben (e) Propylparaben (e) Isobutylparaben Water (e) Sodium hydroxide qs to pH 7.00 Fragrance% weight / weight (as supplied)

2.00

1.00

5.00

5.00

5.00

3.00

1.00

0.10

5.00 qs for 100

3.00

0.50

8.00

1.00 qs to pH 7.00 qs

Part F Part G Preparation

Parts A and B are heated separately to 80 ° C. Part B is poured into part A with moderate agitation. The mixture is homogenized with an Ultra Turrax at 11,000 rpm for 1 minute. After cooling to 70 ° C, part C is added with stirring. After additional cooling to 50 ° C, part D is incorporated very slowly. At 40 ° C part E is added. At room temperature the pH is adjusted with part F to 7.00 and part G is added.

Example 24: UVA-UVB sunscreen lotion, oil / water type

Composition Name INCI % weight / weight (as supplied) 2.00 Part A Cetyl potassium phosphate 5 Tricontanil PVP 1.00 Caprylic / capric triglyceride 5.00 C12-15 alkyl benzoate 5.00 Cetearyl isononanoate 5.00 Glyceryl stearate 3.00 10 Cetyl alcohol 1.00 Dimethicone 0.10 Ethylexyl methoxycinnamate 5.00 Part B Water qs to 100 Glycerin 3.00 15 Part C Estearet-10 allyl ether / acrylates copolymer 0.50 Part D Dispersion of UV absorber according to prepared in Example 6 20.00 Part E Phenoxyethanol (e) Methylparaben (e) Ethylparaben (e) Butylparaben (e) 20 Propylparaben (e) Isobutylparaben 1.00 Part F Water (e) Sodium hydroxide qs to pH 7.00 qs to pH 7.00 Part G Fragrance what

Preparation

Parts A and B are heated separately to 80 ° C. Part B is poured into part A under moderate agitation. The mixture is homogenized with an Ultra Turrax at 11,000 rpm for 1 minute. After cooling to 70 ° C, part C is added with stirring. After additional cooling to 50 ° C, part D is incorporated very slowly. At 40 ° C part E is added. At room temperature the pH is adjusted with part F to 7.00 and part G is added.

Example 25: Sunscreen lotion

Composition Name INCI% weight / weight (as supplied)

Part A

Part B

Part C

Cetearyl alcohol (e) Dicetyl phosphate (e) phosphate Cetet-10 4.00 C12-15 alkyl benzoate 2.00 Tipprylic Ether 3.00 Ethoxydiglycol oleate 2.00 Stearic acid 1.00 Ethylexyl methoxycinnamate 3.00 Copolymer sodium acrylate (e) Glycine Soy (e) PPG-1 Tridecet-6 0.30 Squalane 3.50 VP / eicosene copolymer 2.00 Water qs to 100 Dispersion of UV absorber according to prepared in Example 6 5.00 Diazolidinyl urea (e) iodopropynyl butylcarbamate

0.15

Propylene glycol 2.50

Water 10.00

Part D Cyclopentassiloxane (e) dimethicone 2,00

Etoxidiglycol 5.00

Cyclopentassiloxane (e) Dimethicone / Dimethicone Vinyl Cross Polymer 2.00

Part E Water (e) sodium hydroxide qs

Part F Fragrance qs

Preparation

Parts A and part B are heated separately to 75 ° C. Part B is poured into part A under progressive agitation speed. Below 65 ° C, the ingredients of part D are added separately. After cooling to 55 ° C with moderate stirring, part C is added. At

• · ·· · ······ temperature below 35 ° C, the pH is checked and adjusted with sodium hydroxide and homogenized with an Ultra Turrax for 30 seconds at 11,000 rpm.

At room temperature, part F is added.

Example 26: Water / oil sunscreen lotion

Composition Name INCI% weight / weight (as supplied)

Part A PEG-7 hydrogenated castor oil 3.00

Polyglyceryl-3 diisoestearate 4.00

Microcrystalline wax 1.00

Magnesium stearate 1.50

Propylparaben 0.10

Mineral oil 15.00

Octyldodecanol 8.00

Triazole ethylexila 1.00

Ethylexyl methoxycinnamate 2.00

Part B Water qs for 100

Water (e) citric acid 0.05

Methylparaben 0.15

Magnesium sulfate 0.50

Part C Dispersion of UV absorber as prepared in Example 6 9.00

Fragrance qs

Preparation

Part A is heated to 80 ° C while stirring. Part B is added to part A and homogenized with an Ultra Turrax at 11,000 rpm for one minute. After cooling to 30 ° C, part C is incorporated.

Example 27: Sunscreen lotion for water / oil skin protection

Composition Name INCI % weight / weight (as supplied) Part A Polyglyceryl dipyrhydroxystearate-2 3.00 Glyceryl oleate 3.00 Cetearyl isononanoate 7.00 Hexyl laurate 6.00 Tipprylic Ether 6.00 Propylparaben 0.10 Hexildecanol 3.00 Magnesium stearate 1.00 Beeswax 1.00 Ethylexyl methoxycinnamate 4.00 Part B Water qs to 100 Methylparaben 0.15 Magnesium sulfate 1.00 Part C Dispersion of UV absorber according to prepared in Example 6 6.00

Preparation

Part A is heated separately to 80 ° C with gentle agitation. Part B is added to part A and homogenized for one minute at 11,000 rpm. After cooling to 30 ° C, part C is added under constant stirring.

Claims (5)

1. Compounds, characterized by the fact that they present the formula: in which 5 Ri, R2, R3, R4, Rs, R6, R7 θ Re independently of each other are hydrogen; C-i-C-ie alkyl; C2-C18 alkenyl; C5-C7 cycloalkyl; C1-C6 alkylene-C5-C7 cycloalkyl; Rg is hydrogen; C1-C18 alkyl; C2-C18 alkenyl; C5-C7 cycloalkyl; C1-C6 alkylene-C5-C7 cycloalkyl; C6-C10 aryl; 10 A is -NR10-, where R10 has the same meanings as Rg; X is COOR11; CONR12R13; SO3R14; or SO2NR15R16, where Rn, R12, R13, R14, R15 θ R16 have the same meanings independently of each other as Rg. Compound according to claim 1, characterized 15 due to the fact that it presents the formula: on what: Rg, A and X have the same meanings according to claim 1. 3. Compound according to claim 1, characterized by the fact that it presents the formula: 5 in which: Rg is C1-C5 alkyl; and R17 is hydrogen; C1-C12 alkyl or -NH ₂ . 4. Process for the preparation of compounds of formula (1), as defined in claim 1, characterized by the fact that it comprises reaction of one mole of at least one compound of the formula: in which Ri, R2, R3, R4 θ R9 independently have the same meanings as defined in claim 1 or 2; and Y is halogen, 15 with at least two moles of at least one compound of the formula: A-Η (5) in which; Rs, R6, R7, Re θ X independently have the same meanings as defined in claim 1 or 2 independently of each other. 5. Cosmetic preparation, characterized by the fact that it comprises at least one or more compounds of the formula (1), as defined in any one of claims 1 to 3, together with cosmetically tolerable vehicles or adjuvants.