Biodegradable UV absorbers and uses thereof ii

Abstract

The present relates to compounds of formula (I) as defined herein. The compounds are suitable for protection against ultraviolet (UV) radiation. Further, the present invention is concerned with compositions comprising at least one compound of formula (I) and uses of said compounds as UV filters and light stabilizing agents.

Description

[0001] BIODEGRADABLE UV ABSORBERS AND USES THEREOF II

[0002] Field of the invention

[0003] The present invention relates to compounds according to formula (I), as defined herein below, that are useful as organic biodegradable UV absorbers, in particular in personal care and pharmaceutical compositions, such as sunscreen and daily care compositions with photoprotection. The present invention furthermore relates to such compositions containing the UV absorbers as well as their corresponding use.

[0004] Background of the invention

[0005] UV radiation causes harmful effects on the human skin. Beside the acute effect of sunburn of the skin, UV radiation is also known to increase the risk of skin cancer. Furthermore, long time exposure to UV-A and UV-B light can cause phototoxic and photo allergenic reactions on the skin and can accelerate skin aging. UV radiation is further known to lead to the photolytic degradation of various components in complex mixtures, such as cosmetics, pharmaceuticals, food and beverages, as well as home care and cleaning compositions. Such sensitive ingredients include various colorants that have become more and more important, as they support brand recognition by consumers and avoid cross-contamination by the user in industrial and institutional cleaning applications.

[0006] To protect the human skin from UV radiation, various sun protecting UV filters (also referred to as UV absorbers) exist including UV-A filter, UV-B filter, and broadband filters. These filters are added to e.g. sunscreen or cosmetic compositions. The UV filters are either organic or inorganic, particulate or nonparticulate compounds, of which all have a high absorption efficacy in the UV-light range. In general, UV light can be divided into UV-A radiation and UV-B radiation. Depending on the position of the absorption maxima, UV filters are divided into UV-A and UV-B filters. In case an UV filter absorbs both, UV-A and UV-B light, it is referred to as a broadband absorber.

[0007] To protect UV sensitive components and ingredients in cosmetics, pharmaceuticals, food and beverages, as well as home care and cleaning compositions, various light stabilizing agents are known and widely used in the art. However, many of these compounds lack versatility to be used in a wide range of different compositions or have drawbacks related to toxicity, environmental considerations, and legal restrictions. Specifically, the EU ecolabel is used to assure the consumer of a non-toxic and environmentally safe product. As the EU ecolabel is a decisive factor in consumer and customer awareness, it is generally desirable to provide compositions that are non-toxic and environmentally safe which in turn requires that all ingredients are carefully selected to meet the respective legal requirements for such labeling. Consequently, there is need in the field for UV light stabilizers that meet the strict requirements for the EU ecolabel and at the same time provide for the same or even better stabilizing effects than the currently used compounds.

[0008] Achieving a more sustainable chemical industry is generally one of the clear objectives pursued by EU legislation, incorporating the replacement of ingredients having a negative environmental impact such as a negative effect on the endocrine system, persistence, bioaccumulation and or toxicity. In line with these objectives, EU regulations on the use of certain chemicals for some applications become increasingly strict. This is for instance the case for UV filters used in sunscreen applications and UV stabilizers for several other applications.

[0009] Current solutions on the market on the one hand are not fully biodegradable, and on the other hand present toxicity concerns. In fact, the vast majority of (cosmetic) registered organic UV filters are resistant to environmental degradation through chemical, biological, and photolytic processes. Because of their persistence, they bioaccumulate with potential adverse impact on human health and the environment. Due to their wide release into the environment, and especially in the oceans, the demand for biodegradable UV filters is growing.

[0010] In this context, cosmetics product regulations (CPR) will on a noticeably short timescale certainly ban many of the current solutions. In this context and also in view of the increasing importance of the EU ecolabel, innovative and more sustainable (biodegradable) UV filters and UV stabilizer solutions urgently need to be developed and brought to the market to replace current solutions

[0011] The present invention meets this demand by providing novel types of organic UV filters that are more biodegradable than currently used compounds.

[0012] Summary of the invention

[0013] The present invention is based on the finding that specific compounds of formula (I) (2-hydroxy chalcone derivatives) as well as the salts, hydrates, tautomers, and stereoisomers thereof are suitable as UV absorbers while also being biodegradable.

[0014] In a first aspect, the present invention is thus directed to a compound of formula (I)

[0015]

[0016] or the salt, hydrate, tautomer or stereoisomer thereof;

[0017] wherein

[0018] R1, R2, R4, R5and R6are H;

[0019] R3is H or -O(C3-C10alkyl);

[0020] R7and R8are selected from H and phenyl of formula (II) wherein at least one of R7and R8is not H

[0021]

[0022] wherein

[0023] R11, R13and R15are independently selected from H, C3-C10alkyl, and -O(C3-C10alkyl);

[0024] R12and R14are independently selected from H, C3-C10 alkyl, -0(C3-Cio alkyl), and -N(C1-C4alkyl); wherein at least one of R11, R12, R13, R14and R15is not H;

[0025] and

[0026] wherein if R11, R12, R14and R15are H and R13is isopropyl or -O-isopropyl, R3is not H and wherein if R12is -O(C6alkyl), R3, R4, R5, R11, R13, R14and R15are not all H;

[0027] if R14is -O(C6alkyl), R3, R4, R5, R11, R12, R13, and R15are not all H; and

[0028] if R15is -O(C6alkyl), R3, R4, R5, R11, R12, R13, and R14are not all H.

[0029] In another aspect, the invention is directed to a compound of formula (I) or a salt, hydrate, tautomer or stereoisomer thereof wherein,

[0030] R1, R2, and R6are H;

[0031] R3is H or -O(C3-C10alkyl);

[0032] R4is H or C1-C4 alkyl;

[0033] R5is H or -O(C1-C4alkyl);

[0034] R7and R8are selected from H, optionally substituted pyrrole, substituted furan, substituted benzofuran, optionally substituted indole,

[0035] wherein at least one of R7and R8is not H;

[0036] wherein pyrrole, furan, benzofuran or indole, if substituted, are substituted by one to three substituents selected from C1-C10 alkyl, and -0(Ci-Cio alkyl);

[0037] wherein if one of R7and R8is optionally substituted indole or benzofuran and the other is H, R3is not H.

[0038] In various embodiments of the above compounds,

[0039] (1) R3is H, -O(2-ethylhexyl), -O(methyl), or-O(isopropyl) and R2, R4and R5are optionally H;

[0040] (2) R4is H or methyl and R2, R3and R5are optionally H;

[0041] (3) R5is H or methoxy and R2, R3and R4are optionally H;

[0042] (4) R8is phenyl of formula (II), R11is -O(n-propyl), -O(n-pentyl), -O(n-octyl), or -O(2-ethylhexyl), and R12, R13, R14and R15are optionally H;

[0043] (5) R8is phenyl of formula (II), R12is -O(n-propyl), -N(ethyl)2, and R11, R13, R14and R15are optionally H;

[0044] (6) R8is phenyl of formula (II), R13is -O(isopropyl), -O(n-pentyl), -O(n-hexyl), or -O(2-ethylhexyl), and R11, R12, R14and R15are optionally H;

[0045] (7) R8is phenyl of formula (II), R11and R12are -O(n-propyl) and R13, R14and R15are optionally H; (8) R8is phenyl of formula (II), R11and R13are -O(n-pentyl) and R12, R14and R15are optionally H; (9) R3and R5are -O(methyl) and R2and R4are optionally H; and / or

[0046] (10) R8is 5-methyl-2-furanyl, 3-pyrrolyl, 2-benzofuranyl, or 3-indolyl.

[0047] In various embodiments, the compound of formula (I) is selected from the following compounds of formula (I), wherein:

[0048] (1) R8is phenyl, R13is -O(2-ethylhexyl) and R1, R2, R3, R4, R5, R6, R7, R11, R12, R14and R15are H; (2) R8is phenyl, R11is -O(2-ethylhexyl) and R1, R2, R3, R4, R5, R6, R7, R12, R13, R14and R15are H; (3) R8is phenyl, R3and R13are -O(2-ethylhexyl) and R1, R2, R4, R5, R6, R7, R11, R12, R14and R15are H;

[0049] (4) R8is phenyl, R3is -O(2-ethylhexyl), R13is isopropyl, and R1, R2, R4, R5, R6, R7, R11, R12, R14and R15are H;

[0050] (5) R8is phenyl, R3is -O(methyl), R11and R12are -O(n-propyl), and R1, R2, R4, R5, R6, R7, R13, R14and R15are H;

[0051] (6) R8is phenyl, R11and R13are -O(n-pentyl), and R1, R2, R3, R4, R5, R6, R7, R12, R14and R15are H; (7) R8is phenyl, R11is -O(n-octyl) and R1, R2, R3, R4, R5, R6, R7, R12, R13, R14and R15are H;

[0052] (8) R8is phenyl, R12is -N(ethyl)2and R1, R2, R3, R4, R5, R6, R7, R11, R13, R14and R15are H;

[0053] (9) R8is phenyl, R3and R5are -O(methyl), R13is -O(n-hexyl), and R1, R2, R4, R6, R7, R11, R12, R14and R15are H;

[0054] (10) R8is 5-methyl-2-furanyl, R4is methyl, and R1, R2, R3, R5, R6, and R7are H;

[0055] (11) R8is 3-pyrrolyl, and R1, R2, R3, R4, R5, R6, and R7are H;

[0056] (12) R8is 2-benzofuranyl, R3is -O(2-ethylhexyl), and R1, R2, R4, R5, R6, and R7are H;

[0057] (13) R8is 2-benzofuranyl, R3is -O(isopropyl), and R1, R2, R4, R5, R6, and R7are H;

[0058] (14) R8is 3-pyrrolyl, R3is -O(2-ethylhexyl), and R1, R2, R4, R5, R6, and R7are H; or

[0059] (15) R8is 3-indolyl, R3is -O(2-ethylhexyl), and R1, R2, R4, R5, R6, and R7are H.

[0060] The compounds disclosed herein preferably have a biodegradability of at least 10%, preferably at least 20% degradation, more preferably at least 30%, even more preferably at least 40%, 50% or 60% degradation, as determined over 28 days at 22°C according to OECD 301F.

[0061] In another aspect, the present invention features a composition, preferably a pharmaceutical or personal care composition, comprising (1) at least one of the above compounds of formula (I), and

[0062] (2) at least one other component selected from the group consisting of: UV filters different from the compounds of formula (I), emulsifiers, emollients, thickeners, cosmetic oils, sensory enhancers, consistency agents, film forming agents, UV performance boosters, preservatives, and perfumes.

[0063] In various embodiments the above composition further comprises at least one further UV filter different to the compounds of formula (I), preferably selected from

[0064] (1) at least one UVA filter, preferably selected from the group consisting of disodium phenyl dibenzimidazole tetrasulfonate, hexyl 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoate (INCI diethylamino hydroxybenzoyl hexyl benzoate), methoxypropylamino cyclohexenylidene ethoxyethylcyanoacetate (MCE), 1-(4-(1,1-dimethylethyl)phenyl)-3-(4-methoxyphenyl)propane-1,3-dione (INCI butyl methoxydibenzoylmethane), terephthalylidene dicamphor sulfonic acid, and combinations thereof; and / or (2) at least one UVB filter, preferably selected from the group consisting of 4,4’,4”-(1,3,5-triazine-2,4,6-triyltriimino)tris-benzoic acid-tris(2-ethylhexyl)ester (INCI ethylhexyl triazone), 4,4’-[[6-[[4-[[(1,1-dimethylethyl)amino]carbonyl]phenyl]amino]-1,3,5-triazin-2,4-diyl]diimino]bis-benzoic acid-bis(2-ethylhexyl)ester (INCI diethylhexyl butamido triazone), phenylbenzimidazole sulfonic acid,, and combinations thereof; and / or (3) at least one broadband UV filter, preferably selected from the group consisting of bisethylhexyloxyphenol methoxyphenyl triazine (INCI bis-ethylhexyloxyphenol methoxyphenyl triazine), 2-(2H-benzotriazol-2-yl)-6-[(2-ethylhexyloxy)methyl]-4-methylphenol, 2-(2H-benzotriazol-2-yl)-4-methyl-6-[2-methyl-3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]-1-disiloxanyl]propyl]phenol (INCI drometrizole trisiloxane), 2,2'-methylenbis[6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol] (INCI methylene Bis-benzotriazolyl tetramethylbutylphenol), phenylene bis-diphenyltriazine (PBDT), and combinations thereof; and / or

[0065] (4) at least one organic particulate UV filter is selected from the group consisting of 2,2'-methylene bis[6- (2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol] (INCI methylene bis-benzotriazolyl tetramethylbutylphenol), 2,4,6-tris(biphenyl-4-yl)-1,3,5-triazine (INCI tris-biphenyl triazine), 1,1 ’-(1,4-pipe razined iy I) bis[1 -[2-[4-(diethylamino)-2-hydroxybenzoyl]phenyl]-methanone (INCI bis- (diethylaminohydroxybenzoyl benzoyl) piperazine), 5,6,5’,6’-tetraphenyl-3-3’-(1,4-phenylene)bis(1,2,4-triazine) (INCI phenylene bis-diphenyltriazine, PBDT), micronized 1,4-di(benzoxazole-2'-yl)benzene and combinations thereof; and / or

[0066] (5) at least one inorganic UV filter, preferably selected from the group consisting of titanium dioxide, zinc oxide, iron oxide, cerium oxide and mixtures thereof; and / or

[0067] (6) at least one organic UV filter, preferably selected from the group consisting of ethylhexyl methoxycinnamate, ethylhexyl salicylate, homosalate, amiloxate, padimate O, shinorine, gadusol, mycosporine-2 glycine, porphyra-334, or cyanoacrylates, the cyanoacrylates optionally being selected

[0068]

[0069] (7) at least one organic UV filter, preferably selected from the group consisting of croconic acid derivatives, N-[(3E)-3-[(4-Methoxyphenyl)imino]-5,5-dimethyl-1-cyclohexen-1-yl]glycine, caprylyloxyphenylamino dimethyltetrahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylhexahydro benzothiazine carboxylic acid, Ethyl (3R)-3,4,5,6,7,8-hexahydro-8-[(4-methoxyphenyl)imino]-6,6-dimethyl-2H-1,4-benzothiazine-3-carboxylate, methoxyphenylimino dimethylcyclohexenyl ethyl glycinate, feruloyl hemp glycerides, feruloyl glycerides, feruloyl soybean glyceride FSG-33, feruloyl coconut glyceride FCG-33, feruloyl hemp glyceride FHG-33, ferulic acid, caffeic acid phenethyl ester, quercetin, methylsalicylate, vanillic acid, methyl anthranilate, rutin, hispolon, Bis(cyano butylacetate) anthracenediylidene, trolamine salicylate, resveratrol trimethyl ether, ethyl ferulate, chlorogenic acid, methyl vanillate, ethyl protocatechuate, genistein, ellagic acid, pongamol, daidzein, luteolin, acetovanillone, caffeic acid, kaempferol, apigenin, sinapic acid, folic acid, troxerutin, p-coumaric acid, melanin, 3,4,5-trimethoxycinnamic acid, Kaempferia galanga root extract, ethylhexyl methoxycrylene, protocatechu ic acid, lignin, lignosulfonate, coffee bean extract, mycosporine-like amino acids, gadusosporines, hipposudoric acid, norhipposudoric acid, 2-Methylphenyl (2E)-3-(4-methoxyphenyl)-2-propenoate, 2-Propenoic acid, 3-(4-methoxyphenyl)-, 2-methylphenyl ester

[0070] In another aspect, the present invention features a composition, preferably a pharmaceutical or personal care composition, comprising at least one compound of formula (I)

[0071]

[0072] or a salt, hydrate, tautomer or stereoisomer thereof;

[0073] wherein

[0074] R1is H or methyl;

[0075] R2, R3, R4and R5are independently selected from H, C1-C10 alkyl and -0(Ci-Cio alkyl) or R4and R5combine to form together with the carbon atoms to which they are attached a phenyl ring;

[0076] R6is H or -O-R9;

[0077] R7and R8are selected from H, -Ar or C1-C10 alk(en)ylene-Ar, wherein Ar is an optionally substituted aryl or heteroaryl group, wherein at least one of R7and R8is not H; or

[0078] R5and one of R7and R8combine to form an -O- group;

[0079] R9is optionally substituted 5- or 6-membered heterocyclyl;

[0080] wherein if an aryl or heteroaryl group is substituted, it is substituted by 1 to 3 substituent(s) selected from C1-C10 alkyl, -OH, -O(Ci-C4 alkyl), -C(=O)-O(C1-C4alkyl), -N(C1-C4alkyl)2, aryl, and C1-C10alk(en)ylene-aryl, or two (vicinal) substituents combine to form a cyclic group of the formula -O-(CH2)n-O- with n being 1 or 2; and

[0081] wherein if a heterocyclyl group is substituted, it is substituted by one or more substituents selected from -OH, C1-C4 alkyl and (C1-C4 alkylene)-OR10, wherein R10is 5- or 6-membered heterocyclyl optionally substituted by one or more substituents selected from -OH and methyl; and

[0082] (2) at least one further UV filter different to the compounds of formula (I), preferably selected from

[0083] (i) at least one UVA filter, preferably selected from the group consisting of disodium phenyl dibenzimidazole tetrasulfonate, hexyl 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoate (INCI diethylamino hydroxybenzoyl hexyl benzoate), methoxypropylamino cyclohexenylidene ethoxyethylcyanoacetate (MCE), 1-(4-(1,1-dimethylethyl)phenyl)-3-(4-methoxyphenyl)propane-1,3-dione (INCI butyl methoxydibenzoylmethane), terephthalylidene dicamphor sulfonic acid, and combinations thereof; and / or

[0084] (ii) at least one UVB filter, preferably selected from the group consisting of 4,4’,4”-(1,3,5-triazine-2,4,6-triyltriimino)tris-benzoic acid-tris(2-ethylhexyl)ester (INCI ethylhexyl triazone), 4,4’-[[6-[[4-[[(1,1-dimethylethyl)amino]carbonyl]phenyl]amino]-1,3,5-triazin-2,4-diyl]diimino]bis-benzoic acid-bis(2- ethylhexyl)ester (INCI diethylhexyl butamido triazone), phenylbenzimidazole sulfonic acid,, and combinations thereof; and / or

[0085] (iii) at least one broadband UV filter, preferably selected from the group consisting of bisethylhexyloxyphenol methoxyphenyl triazine (INCI bis-ethylhexyloxyphenol methoxyphenyl triazine), 2-(2H-benzotriazol-2-yl)-6-[(2-ethylhexyloxy)methyl]-4-methylphenol, 2-(2H-benzotriazol-2-yl)-4-methyl-6-[2-methyl-3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]-1-disiloxanyl]propyl]phenol (INCI drometrizole trisiloxane), 2,2'-methylenbis[6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol] (INCI methylene Bis-benzotriazolyl tetramethylbutylphenol), phenylene bis-diphenyltriazine (PBDT), and combinations thereof; and / or

[0086] (iv) at least one organic particulate UV filter is selected from the group consisting of 2,2'-methylene bis[6- (2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol] (INCI methylene bis-benzotriazolyl tetramethylbutylphenol), 2,4,6-tris(biphenyl-4-yl)-1,3,5-triazine (INCI tris-biphenyl triazine), 1,1 ’-(1,4-pipe razined iy I) bis[1 -[2-[4-(diethylamino)-2-hydroxybenzoyl]phenyl]-methanone (INCI bis- (diethylaminohydroxybenzoyl benzoyl) piperazine), 5,6,5’,6’-tetraphenyl-3-3’-(1,4-phenylene)bis(1,2,4-triazine) (INCI phenylene bis-diphenyltriazine, PBDT), micronized 1,4-di(benzoxazole-2'-yl)benzene and combinations thereof; and / or

[0087] (v) at least one inorganic UV filter, preferably selected from the group consisting of titanium dioxide, zinc oxide, iron oxide, cerium oxide and mixtures thereof; and / or

[0088] (vi) at least one organic UV filter, preferably selected from the group consisting of ethylhexyl methoxycinnamate, ethylhexyl salicylate, homosalate, amiloxate, padimate O, shinorine, gadusol, mycosporine-2 glycine, porphyra-334, or cyanoacrylates, the cyanoacrylates optionally being selected

[0089]

[0090] (vii) at least one organic UV filter, preferably selected from the group consisting of croconic acid derivatives, N-[(3E)-3-[(4-Methoxyphenyl)imino]-5,5-dimethyl-1 -cyclohexen-1 -y l]g lyci n e, caprylyloxyphenylamino dimethyltetrahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylhexahydro benzothiazine carboxylic acid, Ethyl (3R)-3,4,5,6,7,8-hexahydro-8-[(4-methoxyphenyl)imino]-6,6-dimethyl-2H-1,4-benzothiazine-3-carboxylate, methoxyphenylimino dimethylcyclohexenyl ethyl glycinate, feruloyl hemp glycerides, feruloyl glycerides, feruloyl soybean glyceride FSG-33, feruloyl coconut glyceride FCG-33, feruloyl hemp glyceride FHG-33, ferulic acid, caffeic acid phenethyl ester, quercetin, methylsalicylate, vanillic acid, methyl anthranilate, rutin, hispolon, Bis(cyano butylacetate) anthracenediylidene, trolamine salicylate, resveratrol trimethyl ether, ethyl ferulate, chlorogenic acid, methyl vanillate, ethyl protocatechuate, genistein, ellagic acid, pongamol, daidzein, luteolin, acetovanillone, caffeic acid, kaempferol, apigenin, sinapic acid, folic acid, troxerutin, p-coumaric acid, melanin, 3,4,5-trimethoxycinnamic acid, Kaempferia galanga root extract, ethylhexyl methoxycrylene, protocatechuic acid, lignin, lignosulfonate, coffee bean extract, mycosporine-like amino acids, gadusosporines, hipposudoric acid, norhipposudoric acid, 2-Methylphenyl (2E)-3-(4-methoxyphenyl)-2-propenoate, 2-Propenoic acid, 3-(4-methoxyphenyl)-, 2-methylphenyl ester; and, optionally,

[0091] (3) at least one other component selected from the group consisting of: emulsifiers, emollients, thickeners, cosmetic oils, sensory enhancers, consistency agents, film forming agents, UV performance boosters, preservatives, and perfumes.

[0092] In various embodiments of the compositions, in the compound of formula (I)

[0093] (1) R1is H or methyl, preferably H;

[0094] (2) R2is H;

[0095] (3) R3is H, methyl, hydroxy, -O(2-ethylhexyl), -O(methyl), or -O(isopropyl);

[0096] (4) R4is H or methyl or combines with R5to form together with the carbon atoms to which they are attached a phenyl ring;

[0097] (5) R5is H or methoxy, or combines with R4to form together with the carbon atoms to which they are attached a phenyl ring, or combines with R7to form an -O- group;

[0098] (6) R6is H or O-heterocyclyl of formula (III)

[0099] (

[0100]

[0101] group; and / or

[0102] (8) R8is optionally substituted aryl or heteroaryl, preferably, optionally substituted pyrrole, optionally substituted furan, optionally substituted benzofuran, optionally substituted indole, and phenyl of formula (II)

[0103]

[0104] wherein R11, R13and R15are independently selected from H, C3-C10 alkyl, and -O(C3-C10alkyl); and R12and R14are independently selected from H, C3-C10 alkyl, -O(C3-C10alkyl), and -N(C1-C4alkyl).

[0105] In various of these embodiments, R8is 3-pyrrolyl, N-methyl-3-pyrrolyl, 3-furanyl, 5-methyl-3-furanyl, 2-benzofuranyl, 3-indolyl, N-methyl-3-indolyl, 5-methoxyindolyl, 4-methoxyphenyl, 4-isopropylphenyl, 4-(2- ethylhexoxy)phenyl, 2-(2-ethylhexoxy)phenyl, phenyl, 4-isopropoxyphenyl, 1,3-benzodioxol-5-yl, 2,4-dimethoxyphenyl, 2-methoxyphenyl, 4-(diethylamino)phenyl, 2,4-dihydroxyphenyl, 2,3-dipropoxyphenyl, 2,4-di-n-hexoxyphenyl, 2-n-octoxyphenyl, 2-hydroxyphenyl, 4-((E)-ethen-2-yl salicylate)phenyl, 3-(diethylamino)phenyl, 4-n-hexoxyphenyl, 4-biphenyl, 4-naphthyl, 4-carboxyethylphenyl, or (E)-ethen-2-yl phenyl.

[0106] In various embodiments, the compositions comprise a compound selected from the following:

[0107]

[0108]

[0109]

[0110] or a salt, hydrate, tautomer or stereoisomer thereof

[0111] The preferred compound to be used in these compositions is any one of:

[0112]

[0113] or a salt, hydrate, tautomer or stereoisomer thereof.

[0114] In various embodiments, the composition is a pharmaceutical, home care or personal care composition, preferably a sunscreen or daily care composition.

[0115] In various embodiments, the compositions, such as pharmaceutical or personal care composition, can additionally comprise one or more further biodegradable compounds, including those selected from the group consisting of C12-C15alkyl benzoates, coco glycerides, coconut oil, dibutyl adipate, dodecyl lactate, ethylhexyl benzoate, glycerol, glyceryl stearate, lauryl glycoside, lauryl lactate, triglycerides, phenoxyethanol, phenoxy ethyl caprylate, polyglyceryl-2-dipolyhydroxy-stearate, stearoyl glutamate and salts, such as the sodium salt, thereof, stearyl alcohol, dicarboxymethyl alaninate and salts, such as the sodium salt, thereof, and xanthan gum as well as combinations thereof.

[0116] In a still further aspect, the present invention is directed to the compounds or compositions described herein for use to protect skin against UV radiation or to protect UV sensitive components against photolytic degradation.

[0117] In still another aspect, the present invention relates to the use of a compound of formula (I) as disclosed herein as an organic UV filter or as a light stabilizer to protect ingredients against photolytic degradation in a pharmaceutical, personal care, home care, or industrial and institutional cleaning composition.

[0118] In various embodiments, said use includes the compounds defined above in the former aspects of the invention.

[0119] In various embodiments of the composition or the use, the compound of formula (I) as described herein above is comprised in said composition in an amount relative to the total weight of the composition of 0.5 to 50 wt.-%, preferably from 1 to 45 wt.-%, more preferably from 2 to 40 wt.-%, and in particular from 2.5 to 35 wt.-%.

[0120] In all embodiments of the present invention, the compounds of formula (I) preferably have a biodegradability of at least 20% degradation as determined over 28 days at 22°C according to OECD 301F. In various embodiments of the compositions and uses, any organic components of the composition optionally have a biodegradability of at least 20% degradation as determined over 28 days at 22°C according to OECD 301F. Detailed description

[0121] Before describing embodiments of the present invention in detail, definitions important for understanding the present invention are given.

[0122] As used in this specification and in the appended claims, the singular forms of "a" and "an" also include the respective plurals unless the context clearly dictates otherwise.

[0123] In the context of the present invention, the terms "about" and "approximately" denote an interval of accuracy that a person skilled in the art will understand to still ensure the technical effect of the feature in question. The term typically indicates a deviation from the indicated numerical value of ±20%, preferably ±15%, more preferably ±10%, and even more preferably ±5%.

[0124] It is to be understood that the term "comprising" is not limiting. For the purposes of the present invention, the term "consisting of is considered to be a preferred embodiment of the term "comprising of. If hereinafter a group is defined to comprise at least a certain number of embodiments, this is meant to also encompass a group, which preferably consists of these embodiments only.

[0125] Furthermore, the terms "first", "second", "third" or "(i)", "(ii)", "(iii)", "(iv)" etc. and the like in the description and in the claims, are used for distinguishing between similar elements and not necessarily for describing a sequential or chronological order. It is to be understood that the terms so used are interchangeable under appropriate circumstances and that the embodiments of the invention described herein are capable of operation in other sequences than described or illustrated herein.

[0126] As used herein the term “free of in the context that the composition of the present invention is free of a specific compound or group of compounds, which may be combined under a collective term, means that the composition does not comprise said compound or group of compounds in an amount of more than 0.8% by weight, based on the total weight of the composition. Furthermore, it is preferred that the composition according to the present invention does not comprise said compounds or group of compounds in an amount of more than 0.5% by weight, preferably the composition does not comprise said compounds or group of compounds at all. The same definition is applied for the term “does not comprise”. Furthermore, it is to be understood that the term “free of’ or “does not comprise”, in case the composition does not comprise a compound X and a compound Y means that the compositions must be free of both compounds X and Y. In other words, the composition may not contain any compound selected from X and Y.

[0127] When referring to compositions and the weight percent of the therein comprised ingredients it is to be understood that according to the present invention the overall amount of ingredients does not exceed 100% (± 1% due to rounding).

[0128] It is to be understood that this invention is not limited to the particular methodology, protocols, reagents etc. described herein as these may vary. It is also to be understood that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to limit the scope of the present invention that will be limited only by the appended claims. Unless defined otherwise, all technical and scientific terms used herein have the same meanings as commonly understood by one of ordinary skill in the art.

[0129] The term "compound(s) according to the invention", or "compounds of formula (I)" comprises the compound(s) as defined herein as well as a stereoisomer or tautomer thereof.

[0130] Depending on the substitution pattern, the compounds according to the invention may have one or more centers of chirality. The invention provides both the single pure enantiomers or pure diastereomers of the compounds according to the invention, and their mixtures and the use according to the invention of the pure enantiomers or pure diastereomers of the compounds according to the invention or their mixtures. Suitable compounds according to the invention also include all possible geometrical stereoisomers (cis / trans isomers or E / Z isomers) and mixtures thereof. The term "stereoisomer(s)" encompasses both optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one center of chirality in the molecule, as well as geometrical isomers (cis / trans isomers). The present invention relates to every possible stereoisomer of the compounds of formula (I), i.e. to single enantiomers or diastereomers, as well as to mixtures thereof. All compounds of formula (I) disclosed herein therefore comprise the E as well as the Z isomer, although typically only the E isomer is depicted.

[0131] The compounds of formula (I) may be amorphous or may exist in one or more different crystalline states (polymorphs) which may have different macroscopic properties such as stability or show different biological properties such as activities. The present invention relates to amorphous and crystalline compounds of formula (I), mixtures of different crystalline states of the respective compound of formula (I).

[0132] Tautomers may be formed, if a substituent is present at the compound of formula (I), which allows for the formation of tautomers such as keto-enol tautomers or the like.

[0133] Stereoisomers include the E and Z isomers of the compounds of formula (I). In some instances, the E isomers, as shown in the structures herein below, may be preferred.

[0134] The organic moieties mentioned in the above definitions of the variables are collective terms for individual listings of the individual group members. The prefix Cn-Cmindicates in each case the possible number of carbon atoms in the group.

[0135] The term "alkyl" as used herein denotes in each case a straight-chain or branched alkyl group having usually from 1 to 8 carbon atoms, preferably from 1 to 4 carbon atoms. Examples of an alkyl group are methyl, ethyl, n-propyl, iso-propyl, n-butyl, 2-butyl, iso-butyl, tert-butyl, n-pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethyl propyl, 1,1 -dimethylpropyl, 1,2-dimethylpropyl, n-hexyl, n-octyl, 2-ethylhexyl and the like. In the formula -0(Ci-Cio alkyl), the same alkyl groups may be used and form the corresponding alkoxy groups. The term “alkylene” refers to a bivalent saturated alkyl group. The term “alkenylene” refers to bivalent unsaturated alkenyl group. The term “alk(en)ylene” refers to bivalent groups that may be saturated or unsaturated, i.e. alkyl or alkenyl groups. Alkenyl groups include, but are not limited to vinyl and allyl.

[0136] The term “C(=O)-O-(Cn-Cm-alkyl)” as used herein denotes in each case an alkyloxycarbonyl, referring to a straight-chain or branched alkyloxy group as defined above, which is bonded via the carbon atom of a carbonyl group C(=O) to the remainder of the molecule.

[0137] The term “aryl” or “aromatic carbocycle” preferably includes 6-membered aromatic carbocyclic rings based on carbon atoms as ring members. A preferred example is phenyl. The term also includes compounds which comprise fused aromatic or fused aromatic and non-aromatic rings, such as indane or tetrahydronaphthalene. “Carbocyclic”, as used herein, additionally includes non-aromatic cyclic compounds having only carbon ring atoms, such as cyclopentane or cyclohexane.

[0138] The term “heterocyclic” or “heterocyclyl” includes, unless otherwise indicated, in general a 3- to 9-membered, preferably a 4- to 8-membered or 5- to 7-membered, more preferably 5- or 6-membered, in particular 6-membered monocyclic ring. The heterocycle may be saturated, partially or fully unsaturated, or aromatic, wherein saturated means that only single bonds are present, and partially or fully unsaturated means that one or more double bonds may be present in suitable positions, while the Hückel rule for aromaticity is not fulfilled, whereas aromatic means that the Hückel (4n + 2) rule is fulfilled. The heterocycle typically comprises one or more, e.g. 1, 2, 3, or 4, preferably 1, 2, or 3 heteroatoms selected from N, O and S as ring members, where S-atoms as ring members may be present as S, SO or SO₂. The remaining ring members are carbon atoms. In a preferred embodiment, the heterocycle is an aromatic heterocycle, preferably a 5- or 6-membered aromatic heterocycle comprising one or more, e.g. 1, 2, 3, or 4, preferably 1, 2, or 3 heteroatoms selected from N, O and S as ring members, where S-atoms as ring members may be present as S, SO or SO₂. Examples of aromatic heterocycles are provided below in connection with the definition of “hetaryl”. “Hetaryls” or “heteroaryls” are covered by the term “heterocycles”. The saturated or partially or fully unsaturated heterocycles usually comprise 1, 2, 3, 4 or 5, preferably 1, 2 or 3 heteroatoms selected from N, O and S as ring members, where S-atoms as ring members may be present as S, SO or SO₂. The skilled person is aware that S, SO or SO₂ is to be understood as follows:

[0139]

[0140] Further, a skilled person is aware that resonance structures of the oxidized forms may be possible. Saturated heterocycles include, unless otherwise indicated, in general 3- to 9-membered, preferably 4- to 8-membered or 5- to 7-membered, more preferably 5- or 6-membered monocyclic rings comprising 3 to 9, preferably 4 to 8 or 5 to 7, more preferably 5 or 6 atoms comprising at least one heteroatom, such as pyrrolidine, tetrahydrothiophene, tetrahydrofuran, piperidine, tetrahydropyran, dioxane, morpholine or piperazine.

[0141] The term "hetaryl" or “heteroaryl” or “aromatic heterocycle” or “aromatic heterocyclic ring” includes monocyclic 5- or 6-membered aromatic heterocycles comprising as ring members 1, 2, 3 or 4 heteroatoms selected from N, O and S, where S-atoms as ring members may be present as S, SO or SO₂. Examples of 5- or 6-membered aromatic heterocycles include pyridyl (also referred to as pyridinyl), i.e. 2-, 3-, or 4-pyridyl, pyrimidinyl, i.e. 2-, 4- or 5-pyrimidinyl, pyrazinyl, pyridazinyl, i.e. 3- or 4-pyridazinyl, thienyl, i.e. 2- or 3-thienyl, furyl, i.e. 2-or 3-furyl, pyrrolyl, i.e. 2- or 3-pyrrolyl, oxazolyl, i.e. 2-, 3- or 5-oxazolyl, isoxazolyl, i.e.

[0142] 3-, 4- or5-isoxazolyl, thiazolyl, i.e. 2-, 3- or5-thiazolyl, isothiazolyl, i.e. 3-, 4- or5-isothiazolyl, pyrazolyl, i.e.

[0143] 1-, 3-, 4- or 5-pyrazolyl, i.e. 1-, 2-, 4- or 5-imidazolyl, oxadiazolyl, e.g. 2- or 5-[1,3,4]oxadiazolyl, 4- or 5-(1,2,3-oxadiazol)yl, 3- or 5-(1,2,4-oxadiazol)yl, 2- or 5-(1,3,4-thiadiazol)yl, thiadiazolyl, e.g. 2- or 5-(1,3,4-thiadiazol)yl, 4- or 5-(1,2,3-thiadiazol)yl, 3- or 5-(1,2,4-thiadiazol)yl, triazolyl, e.g. 1H-, 2H- or 3H-1,2,3-triazol-4-yl, 2H-triazol-3-yl, 1H-, 2H-, or 4H-1,2,4-triazolyl and tetrazolyl, i.e. 1H- or 2H-tetrazolyl. Further examples are benzofuranyl, such as 2-benzofuranyl, and indolyl, such as 3-indolyl.

[0144] Aryl, heteroaryl and heterocyclic groups include, but are not limited to, pyrrolyl, N-methyl-pyrrolyl, furanyl, methylfuranyl, benzofuranyl, indolyl, N-methyl-indolyl, methoxyindolyl, methoxyphenyl, isopropylphenyl, (2-ethylhexoxy)phenyl, phenyl, isopropoxyphenyl, 1,3-benzodioxolyl, dimethoxyphenyl, methoxyphenyl, (diethylamino)phenyl, dihydroxyphenyl, dipropoxyphenyl, di-n-hexoxyphenyl, n-octoxyphenyl, hydroxyphenyl, ((E)-ethen-2-yl salicylate)phenyl, n-hexoxyphenyl, biphenyl, and naphthyl.

[0145] When referring to compositions and the weight percent of the therein comprised ingredients it is to be understood that according to the present invention the overall amount of ingredients does not exceed 100% (± 1% due to rounding).

[0146] The term “personal care composition”, as used herein, refers to any product suitable to apply to the human body, e.g. sunscreen compositions, bath and shower products, preparations containing fragrances and odoriferous substances, hair-care products, dentifrices, decorative preparations, and cosmetic formulations containing active ingredients. Specific examples of personal care compositions are, without limitation, sunscreen compositions and daily care compositions. In various embodiments, the personal care compositions, in particular the sunscreen or daily care compositions, have an SPF of at least 15 or of more than 15.

[0147] The term “sunscreen composition” refers to any topical product, which absorbs and may further reflect certain parts of UV radiation. Thus, the term “sunscreen composition” is to be understood as not only including sunscreen compositions, but also any cosmetic compositions that provide UV protection. The term “topical product” refers to a product that is applied to the skin and can refer, e.g., to sprays, lotions, creams, oils, or gels. The sunscreen composition comprises one or more active UV filtering agents, e.g., organic or inorganic UV filters, including those described herein, as well as other ingredients or additives, e.g., emulsifiers, emollients, viscosity regulators, humectants, sensory enhancers, stabilizers, film formers, UV boosters, UV scattering compounds, pH adjusters, preservatives, or perfumes. According to the present invention the sunscreen composition may comprise one or more active agents, e.g., organic UV filters, as well as other ingredients or additives, e.g., emulsifiers, emollients, viscosity regulators, stabilizers, preservatives, or fragrances. A sunscreen composition of the present invention may inter alia be formulated as a water-in-oil (W / O) or an oil-in-water (O / W) dispersion, bi-phasic formulation, lipophilic gel, hydrophilic gel, a vesicular dispersion of an ionic or nonionic amphiphilic lipid, a gel, a solid stick or an aerosol formulation.

[0148] The term “daily care composition” refers to any topical product which is intended to be used daily without or with a UV protection. In case UV protection is included, it absorbs and may further reflect and scatter certain parts of UV radiation and is used as an everyday care product for the human body, e.g., for face or body, and is, in the context of the present invention, referred to as a “daily care composition with photoprotection”. The daily care composition with photoprotection of the present invention typically comprises one or more active agents, e.g., organic and / or inorganic UV filters, including those described herein, as well as other ingredients or additives, e.g., emulsifiers, emollients, viscosity regulators, stabilizers, sensory enhancers, humectants, film formers, UV scattering compounds, UV boosters, pH adjusters, adjuvants, preservatives, or fragrances. Suitable daily care composition with photoprotection according to the present invention are, e.g., leave-on face and body care products. Suitable leave-on products for face and body are, e.g., decorative preparations (or make-up) and skin care preparations.

[0149] Suitable decorative preparations are, e.g., facial make-up in the form of day creams or powder creams, face powder (loose or pressed), foundations, dry and moist make-up rouge or cream make-up, eye-care preparations, e.g. eyeshadow preparations, mascara, eyeliner, eye creams or eye-fix creams; lip-care preparations, e.g. lipsticks, rouge lip gloss, lip contour pencils, nail varnishes, and suntan lotions.

[0150] Suitable skin care preparations are, e.g., moisturizing, refining, and lifting preparations. The cited daily care compositions can be in the form of creams, ointments, pastes, foams, gels, lotions, powders, make-ups, sprays, sticks or aerosols.

[0151] Suitable bath and shower additives are, e.g., shower gels, bath-salts, bubble baths and soaps.

[0152] Suitable preparations containing fragrances and odoriferous substances are in particular scents, perfumes, toilet waters and shaving lotions (aftershave preparations).

[0153] Suitable hair-care products are, e.g., shampoos for humans and animals, in particular dogs, hair conditioners, products for styling and treating hair, perming agents, hairsprays and lacquers, hair gels, hair fixatives and hair dyeing or bleaching agents.

[0154] Suitable dentifrices are, e.g., tooth creams, toothpastes, mouth-washes, mouth rinses, anti-plaque preparations and cleaning agents for dentures.

[0155] Suitable cosmetic formulations containing active ingredients are, e.g., hormone preparations, vitamin preparations, vegetable extract preparations and antibacterial preparations. The cited body-care products can be in the form of creams, ointments, pastes, foams, gels, lotions, powders, make-ups, sprays, sticks or aerosols. They preferably contain the compound of formula (I) in the aqueous phase.

[0156] The term “pharmaceutical composition” refers to a composition containing at least one active ingredient that is used to treat (and thus alleviate) a disease, disorder or the symptoms of a disease or disorder. Also included are compositions that prevent a disease or disorder and thus act prophylactically.

[0157] “Home care composition”, as used herein, relates to cleaning compositions used for objections, such as general cleaning compositions, laundry and dishwashing detergents and the like. More specific example include, without limitation, liquid scouring agents, glass detergents, neutral cleaners (all-purpose cleaners), acid household cleaners (bath), WC cleaners, preferably in washing, rinsing and dishwashing agents, clear rinsing agents, dishwasher detergents, shoe polishes, polishing waxes, floor detergents and polishes, metal, glass and ceramic cleaners, textile-care products, agents for removing rust, color and stains (stain remover salt), furniture and multipurpose polishes and leather dressing agents (leather sprays).

[0158] Typically, household cleaning agents are aqueous or alcoholic (e.g. ethanol or isopropyl alcohol) solutions of one or more of the following components:

[0159] -anionic, nonionic, zwitterionic, amphoteric and / or cationic surfactants;

[0160] -soaps, prepared by saponification of animal and vegetable greases;

[0161] -inorganic acids, like hydrochloric acid, phosphoric acid, or sulfuric acid;

[0162] -for basic products inorganic (such as NaOH or KOH) or organic (such as ethanolamine) bases;

[0163] -abrasives for improved cleaning of surfaces,

[0164] -waxes and / or silicones for maintenance and protection of surfaces;

[0165] -polyphosphates or other complexing agents, such as phosphonates, citrate, (amino)carboxylates, in particular MGDA or GLDA, or inorganic complexing agents, such as carbonates;

[0166] -substances which eliminate hypochlorite or halogens;

[0167] -peroxides comprising bleaching activators like TAED;

[0168] -bleaches, for example percarbonates or perborates or H₂O₂;

[0169] -enzymes;

[0170] -in washing detergents discoloration inhibitors, soil-release compounds, grey scale inhibitors, foam inhibitors, fluorescent whitening agents;

[0171] -cleaning agents based on wax may comprise solvents selected from benzine, turpentine and / or paraffines and emulsifiers based on wax;

[0172] -inorganic builders like silicates, polyphosphates, zeolithes;

[0173] -fillers, such as sulfates;

[0174] -pigments, flakes or soluble dyes;

[0175] -perfumes;

[0176] -(additional) light stabilizers, antioxidants and chelating agents;

[0177] -bittering agents;

[0178] -polymers, such as polyethyleneimines (optionally alkoxylated, for example ethoxylated), polyacrylates, sulfopolymers, such as polyacrylates with sulfonated monomeric units; and -rheology modifiers and thickeners.

[0179] “Industrial and institutional cleaning compositions”, as used herein, relates to cleaning compositions intended for routine cleaning of industrial, commercial, and public institutions, outside of the normal household environment. Examples include, without limitation, cleaning compositions used in industrial (manufacturing) plants, car washes, and dry cleaners.

[0180] The term “light stabilizers” as used herein are compounds suitable for protecting other compounds or compositions against photolytic degradation. The light stabilizer is usually present in such products in a concentration of 50 to 1000 ppm.

[0181] The term “UV-filter” as used herein refers to organic or inorganic compounds, which can absorb may further reflect and scatter UV radiation caused by sunlight. UV-filter can be classified based on their UV protection curve as UV-A, UV-B or broadband filters. Preferably, the term “UV filter” comprises or consists of any UV filter as defined in the Annex VI (version of 11.11.2022) of the Regulation (EC) No 1223 / 2009 of the European Parliament and of the Council.

[0182] The definition of “broadband” protection (also referred to as broad-spectrum or broad protection) may be based for example on the “critical wavelength” or the UVA-PF (UVA protection factor). For broadband coverage, UV-B and UV-A protection must be provided. According to the US requirements, a critical wavelength of at least 370 nm is required for achieving broad spectrum protection. Furthermore, it is recommended by the European Commission that all sunscreens should have an UVA protection factor, which is at least one third of the labelled sun protection factor (SPF), e.g., if the sunscreen composition has an SPF of 30 the UVA protection factor has to be at least 10.

[0183] The term “critical wavelength” is defined as the wavelength at which the area under the UV protection curve (% protection versus wavelength) represents 90 % of the total area under the curve in the UV region (290-400 nm). For example, a critical wavelength of 370 nm indicates that the protection of the sunscreen composition is not limited to the wavelengths of UV-B, i.e., wavelengths from 290-320 nm, but extends to 370 nm in such a way that 90 % of the total area under the protective curve in the UV region are reached at 370 nm.

[0184] The term “photostability” refers to the ability of a UV filter or any other molecule, which is exposed to sunlight, to stay stable upon irradiation. In particular, this means that the compound does not undergo a degradation process upon UV radiation.

[0185] The term “sun protection factor (SPF)” as used herein indicates how well the skin is protected by a sunscreen composition from an erythema (sunburn) induced mainly from UV-B radiation. In particular, the factor indicates how much longer the protected skin may be exposed to the sun without getting a sunburn in comparison to untreated skin. For example, if a sunscreen composition with an SPF of 15 is evenly applied to the skin of a person usually getting a sunburn after 10 minutes in the sun, the sunscreen allows the skilled person to stay in the sun 15 times longer. In other words, SPF 15 means that 1 / 15 of the burning UV radiation will reach the skin, assuming sunscreen is applied evenly at a thick dosage of 2 milligrams per square centimeter (mg / cm2).

[0186] The term “biodegradation” as used herein denotes that microorganism metabolize the material completely to CO₂, energy, water, and biomass in an aerobic process (according to OECD guideline). If not indicated otherwise, biodegradability is assessed herein according to OECD 301 F over a time period of 28 days at 22°C. As used herein, biodegradable includes “partially biodegradable” and “readily biodegradable”. As used herein, if a compound of formula (I) or an organic component of the composition is “partially biodegradable”, this means having a biodegradability of equal to or more than 20% (>20%) but less than 60% (<60%). In particular, partially biodegradable as used herein is defined as >20% but <60% biodegradability as measured by OECD 301 F (BASF screening test) testing.

[0187] As used herein, if a compound of formula (1) or an organic component of the composition is “readily biodegradable”, this means having a biodegradability of larger or equal to 60% (>60%). In particular, readily biodegradable as used herein is defined as >60% biodegradability as measured by OECD 301 F (BASF screening test) testing.

[0188] In general, the biodegradability of an organic component can be assessed via different OECD 301 A-F measurements. With regard to the present invention it is to be understood that the biodegradability has been assessed for compounds of formula (I) according to a measurement of the OECD 301 F testing method defined throughout the present application as OECD 301 F (BASF screening test). The procedure of the OECD 301 F and OECD 301 F (BASF screening test) are described as follows:

[0189] For the principle of the OECD 301 F test reference is made to the OECD Guidelines for the Testing of Chemicals, Section 3, Environmental fate and behavior (doi.org / 10.1787 / 2074577x). A measured volume of inoculated mineral medium, containing a known concentration of test substance (100 mg test substance / L giving at least 50-100 mg ThOD / l; ThOD = theoretical oxygen demand) as the nominal sole source of organic carbon, is stirred in a closed flask at a constant temperature for up to 28 days. The consumption of oxygen is determined either by measuring the quantity of oxygen (produced electrolytically) required to maintain constant gas volume in the respirometer flask, or from the change in volume or pressure (or a combination of the two) in the apparatus. Evolved carbon dioxide is absorbed in a solution of potassium hydroxide or another suitable absorbent. The amount of oxygen taken up by the microbial population during biodegradation of the test substance (corrected for uptake by blank inoculum, run in parallel) is expressed as a percentage of ThOD or, less satisfactorily, COD. ThOD describes the theoretical oxygen demand and COD describes the common oxygen demand.

[0190] OECD 301 F (BASF screening test): Biodegradation in wastewater was tested in triplicate using the OECD 301 F manometric respirometry method. OECD 301 F is an aerobic test that measures biodegradation of a sample by measuring the consumption of oxygen. To a measured volume of medium, 100 mg / L test substance, which is the nominal sole source of carbon is added along with the inoculum (aerated sludge taken from Mannheim waste water treatment plant). This is stirred in a closed flask at a constant temperature of 22 °C for 28 days. The consumption of oxygen is determined by measuring the change in pressure in the apparatus using an OxiTopC. Evolved carbon dioxide is absorbed in a solution of sodium hydroxide. Nitrification inhibitors are added to the flask to prevent usage of oxygen due to nitrification. The amount of oxygen taken up by the microbial population during biodegradation of the test substance (corrected for uptake by blank inoculum, run in parallel) is expressed as a percentage of ThOD (theoretical oxygen demand, which is measured by the elemental analysis of the compound). A positive control Glucose / Glucosamine is run along with the test samples for each cabinet.

[0191] Biodegradation can then be calculated according to the following formula according to the OECD Guideline for the Testing of Chemicals, Section 3

[0192] BOD = (mg O2uptake by test substance – mg O2uptake by blank) / mg test substance in vessel

[0193] % degradation is calculated according to the following formula according to the OECD Guidelines for the Testing of Chemicals, Section 3:

[0194] % degradation = BOD / ThOD x 100

[0195] In this context, the term “organic component” as used above denotes any organic compound, i.e., any compound comprising organic carbon. In the context of the above, this refers to any carbon-containing compound except for the following carbon-containing compounds, which are considered inorganic compounds: carbides, carbonates (salts of carbonic acid characterized by the CO32-anion, and thus not carbonate esters), bicarbonates (salts of carbonic acid characterized by the HCO3-anion), carbonic acid, CO, CO2, and inorganic cyanides (salts characterized by the CN_anion). Further, elemental forms of carbon, such as graphite, diamond, fullerenes, or carbon nanotubes, are not considered organic carbon. Further details of said method can be derived from the examples below.

[0196] Various embodiments regarding the compound of formula (I) as well as the use of the compound of formula (I) to protect skin against UV radiations or as a light stabilizer are described hereinafter. It is to be understood that the preferred embodiments of the invention are preferred alone or in combination with each other. Further, preferred embodiments regarding the cosmetic or pharmaceutical composition comprising a compound of formula (I) as well as the use of such a cosmetic or pharmaceutical composition e.g. in sunscreens are described hereinafter.

[0197] The compounds of the invention are generally compounds according to formula (I)

[0198]

[0199] or the salt, hydrate, tautomer or stereoisomer thereof; wherein

[0200] R1, R2, R4, R5and R6are H;

[0201] R3is H or -O(C3-C10alkyl);

[0202] R7and R8are selected from H, optionally substituted pyrrole, substituted furan, optionally substituted benzofuran, optionally substituted indole, and phenyl of formula (II)

[0203]

[0204] wherein

[0205] R11, R13and R15are independently selected from H, C3-C10alkyl, and -O(C3-C10alkyl);

[0206] R12and R14are independently selected from H, C3-C10 alkyl, -0(C3-Cio alkyl), and -N(C1-C4alkyl); wherein at least one of R7and R8is not H;

[0207] wherein at least one of R11, R12, R13, R14and R15is not H;

[0208] wherein pyrrole, furan, benzofuran or indole, if substituted, are substituted by one to three substituents selected from C1-C10 alkyl, and -O(C1-C10alkyl);

[0209] wherein if one of R7and R8is optionally substituted indole or benzofuran and the other is H, R3is not H; and

[0210] wherein if R11, R12, R14and R15are H and R13is isopropyl or -O-isopropyl, R3is not H.

[0211] In various embodiments, R7and R8are selected from H and phenyl of formula (II) wherein at least one of R7and R8is not H

[0212]

[0213] wherein

[0214] R11, R13and R15are independently selected from H, C3-C10 alkyl, and -O(C3-C10alkyl);

[0215] R12and R14are independently selected from H, C3-C10 alkyl, -O(C3-C10alkyl), and -N(C1-C4alkyl); wherein at least one of R11, R12, R13, R14and R15is not H; and

[0216] wherein if R11, R12, R14and R15are H and R13is isopropyl or -O-isopropyl, R3is not H; and

[0217] wherein if R12is -O(C6alkyl), R3, R4, R5, R11, R13, R14and R15are not all H;

[0218] if R14is -O(C6alkyl), R3, R4, R5, R11, R12, R13, and R15are not all H; and

[0219] if R15is -O(C6alkyl), R3, R4, R5, R11, R12, R13, and R14are not all H.

[0220] In various embodiments, the present invention relates to a compound of formula (I) or a salt, hydrate, tautomer or stereoisomer thereof, wherein

[0221] R1, R2, and R6are H;

[0222] R3is H or -O(C3-C10alkyl);

[0223] R4is H or C1-C4 alkyl;

[0224] R5is H or -O(C1-C4alkyl);

[0225] R7and R8are selected from H, optionally substituted pyrrole, substituted furan, substituted benzofuran, optionally substituted indole,

[0226] wherein at least one of R7and R8is not H;

[0227] wherein pyrrole, furan, benzofuran or indole, if substituted, are substituted by one to three substituents selected from C1-C10 alkyl, and -O(C1-C10alkyl);

[0228] wherein if one of R7and R8is optionally substituted indole or benzofuran and the other is H, R3is not H.

[0229] In some embodiments R7is H and R8is selected from optionally substituted pyrrole, substituted furan, substituted benzofuran, optionally substituted indole, wherein pyrrole, furan, benzofuran or indole, if substituted, are substituted by one to three substituents selected from C1-C10 alkyl, and -O(C1-C10alkyl).

[0230] In some embodiments R8is H and R7is selected from optionally substituted pyrrole, substituted furan, substituted benzofuran, optionally substituted indole, wherein pyrrole, furan, benzofuran or indole, if substituted, are substituted by one to three substituents selected from C1-C10 alkyl, and -O(C1-C10alkyl).

[0231] In exemplary compounds of the above compounds of formula (I), R3is H, -O(2-ethylhexyl), -O(methyl), or -O(isopropyl) and R2, R4and R5are optionally H.

[0232] In exemplary compounds of the above compounds of formula (I), R3is -O(2-ethylhexyl), -O(methyl), or -O(isopropyl) and R2, R4and R5are optionally H.

[0233] In various embodiments, R4is H or methyl and R2, R3and R5are optionally H.

[0234] In various embodiments, R5is H or methoxy and R2, R3and R4are optionally H.

[0235] R8can be phenyl of formula (II), R11is -O(n-propyl), -O(n-pentyl), -O(n-octyl), or -O(2-ethylhexyl), and R12, R13, R14and R15are optionally H.

[0236] In some embodiments, R8is phenyl of formula (II), R12is -O(n-propyl), -N(ethyl)2, and R11, R13, R14and R15are optionally H. In various embodiments, R8is phenyl of formula (II), R13is -O(isopropyl), -O(n-pentyl), -O(n-hexyl), or -0(2-ethylhexyl), and R11, R12, R14and R15are optionally H.

[0237] In some embodiments, R8is phenyl of formula (II), R11and R12are -O(n-propyl) and R13, R14and R15are optionally H.

[0238] In some embodiments, R8is phenyl of formula (II), R11and R13are -O(n-pentyl) and R12, R14and R15are optionally H.

[0239] In some embodiments, R3and R5are -O(methyl) and R2and R4are optionally H.

[0240] In some embodiments, R8is 5-methyl-2-furanyl, 3-pyrrolyl, 2-benzofuranyl, or 3-indolyl.

[0241] All of the above more specific embodiments may be combined, insofar possible.

[0242] Concrete embodiments of the compounds of the invention are the following compounds of formula (I), wherein:

[0243] (1) R8is phenyl, R13is -O(2-ethylhexyl) and R1, R2, R3, R4, R5, R6, R7, R11, R12, R14and R15are H; (2) R8is phenyl, R11is -O(2-ethylhexyl) and R1, R2, R3, R4, R5, R6, R7, R12, R13, R14and R15are H; (3) R8is phenyl, R3and R13are -O(2-ethylhexyl) and R1, R2, R4, R5, R6, R7, R11, R12, R14and R15are H;

[0244] (4) R8is phenyl, R3is -O(2-ethylhexyl), R13is isopropyl, and R1, R2, R4, R5, R6, R7, R11, R12, R14and R15are H;

[0245] (5) R8is phenyl, R3is -O(methyl), R11and R12are -O(n-propyl), and R1, R2, R4, R5, R6, R7, R13, R14and R15are H;

[0246] (6) R8is phenyl, R11and R13are -O(n-pentyl), and R1, R2, R3, R4, R5, R6, R7, R12, R14and R15are H; (7) R8is phenyl, R11is -O(n-octyl) and R1, R2, R3, R4, R5, R6, R7, R12, R13, R14and R15are H;

[0247] (8) R8is phenyl, R12is -N(ethyl)2and R1, R2, R3, R4, R5, R6, R7, R11, R13, R14and R15are H;

[0248] (9) R8is phenyl, R3and R5are -O(methyl), R13is -O(n-hexyl), and R1, R2, R4, R6, R7, R11, R12, R14and R15are H;

[0249] (10) R8is 5-methyl-2-furanyl, R4is methyl, and R1, R2, R3, R5, R6, and R7are H;

[0250] (11) R8is 3-pyrrolyl, and R1, R2, R3, R4, R5, R6, and R7are H;

[0251] (12) R8is 2-benzofuranyl, R3is -O(2-ethylhexyl), and R1, R2, R4, R5, R6, and R7are H;

[0252] (13) R8is 2-benzofuranyl, R3is -O(isopropyl), and R1, R2, R4, R5, R6, and R7are H;

[0253] (14) R8is 3-pyrrolyl, R3is -O(2-ethylhexyl), and R1, R2, R4, R5, R6, and R7are H; or

[0254] (15) R8is 3-indolyl, R3is -O(2-ethylhexyl), and R1, R2, R4, R5, R6, and R7are H.

[0255] In various embodiments, the compound has a biodegradability of at least 20%, at least 30%, at least 40%, at least 50%, at least 60%, at least 65%, at least 70%, at least 75%, at least 80%, at least 85% or at least 90% degradation as determined over 28 days at 22°C according to OECD 301F. In various embodiments, the compound is any of the compounds disclosed in the table below or any one of

[0256]

[0257] As indicated above, the present invention further relates to a composition, comprising

[0258] 1) at least one compound of formula (I) as indicated above, and

[0259] (2) at least one other component selected from the group consisting of: UV filters different from the compounds of formula (I), emulsifiers, emollients, thickeners, cosmetic oils, sensory enhancers, consistency agents, film forming agents, UV performance boosters, preservatives, and perfumes.

[0260] In various embodiments, said at least one other compound, in particular if it is an organic compound, has a biodegradability of at least 20%, at least 30%, at least 40%, at least 50%, at least 60%, at least 65%, at least 70%, at least 75%, at least 80%, at least 85% or at least 90% degradation as determined over 28 days at 22°C according to OECD 301 F

[0261] In various embodiments the above composition further comprises at least one further UV filter different to the compounds of formula (I).

[0262] In another aspect the invention relates to a composition, comprising

[0263] (1) at least one compound of formula (I) according to the present invention as described above or at least one compound according to following formula (I)

[0264]

[0265] or a salt, hydrate, tautomer or stereoisomer thereof;

[0266] wherein

[0267] R1is H or methyl;

[0268] R2, R3, R4and R5are independently selected from H, C1-C10 alkyl and -0(Ci-Cio alkyl) or R4and R5combine to form together with the carbon atoms to which they are attached a phenyl ring;

[0269] R6is H or -O-R9; R7and R8are selected from H, -Ar or C1-C10 alk(en)ylene-Ar, wherein Ar is an optionally substituted aryl or heteroaryl group, wherein at least one of R7and R8is not H; or

[0270] R5and one of R7and R8combine to form an -O- group;

[0271] R9is optionally substituted 5- or 6-membered heterocyclyl;

[0272] wherein if an aryl or heteroaryl group is substituted, it is substituted by 1 to 3 substituent(s) selected from C1-C10 alkyl, -OH, -O(Ci-C4 alkyl), -C(=O)-O(C1-C4alkyl), -N(C1-C4alkyl)2, aryl, and C1-C10alk(en)ylene-aryl, or two (vicinal) substituents combine to form a cyclic group of the formula -O-(CH2)n-O- with n being 1 or 2; and

[0273] wherein if a heterocyclyl group is substituted, it is substituted by one or more substituents selected from -OH, C1-C4 alkyl and (C1-C4 alkylene)-OR10, wherein R10is 5- or 6-membered heterocyclyl optionally substituted by one or more substituents selected from -OH and methyl; and

[0274] (2) at least one further UV filter different to the compounds of formula (I),

[0275] (3) at least one other component selected from the group consisting of: emulsifiers, emollients, thickeners, cosmetic oils, sensory enhancers, consistency agents, film forming agents, UV performance boosters, preservatives, and perfumes.

[0276] In the compositions, in various embodiments, said compound of formula (I) preferably has a biodegradability of at least 20% degradation as determined over 28 days at 22°C according to OECD 301F. In said compositions, in various embodiments, said at least one other compound, in particular if it is an organic compound, preferably has a biodegradability of at least 20% degradation as determined over 28 days at 22°C according to OECD 301F. In various embodiments, this biodegradability requirement applies to both the compounds of formula (I) as well as other compounds, in particular organic compounds, in the composition.

[0277] In these compounds that may be included in the compositions described herein, the various variables in formula (I) may represent the following:

[0278] R1can be H or methyl, preferably H.

[0279] R2is preferably H.

[0280] R3can be H, methyl, hydroxy, -O(2-ethylhexyl), -O(methyl), or -O(isopropyl).

[0281] R4can be H or methyl or combines with R5to form together with the carbon atoms to which they are attached a phenyl ring.

[0282] R5may be H or methoxy, or combines with R4to form together with the carbon atoms to which they are attached a phenyl ring, or combines with R7to form an -O- group.

[0283] R6may be H or O-heterocyclyl, preferably of the formula (III)

[0284]

[0285] Preferably, R6is a H.

[0286] R7may be H or combines with R5to form an -O- group. R8can be optionally substituted aryl or heteroaryl, preferably, optionally substituted pyrrole, optionally substituted furan, optionally substituted benzofuran, optionally substituted indole, and phenyl of formula (II)

[0287]

[0288] wherein R11, R13and R15are independently selected from H, C3-C10 alkyl, and -O(C3-C10alkyl); and R12and R14are independently selected from H, C3-C10 alkyl, -O(C3-C10alkyl), and -N(C1-C4alkyl).

[0289] In various of these embodiments, R8is 3-pyrrolyl, N-methyl-3-pyrrolyl, 3-furanyl, 5-methyl-3-furanyl, 2-benzofuranyl, 3-indolyl, N-methyl-3-indolyl, 5-methoxyindolyl, 4-methoxyphenyl, 4-isopropylphenyl, 4-(2-ethylhexoxy)phenyl, 2-(2-ethylhexoxy)phenyl, phenyl, 4-isopropoxyphenyl, 1,3-benzodioxol-5-yl, 2,4-dimethoxyphenyl, 2-methoxyphenyl, 4-(diethylamino)phenyl, 2,4-dihydroxyphenyl, 2,3-dipropoxyphenyl, 2,4-di-n-hexoxyphenyl, 2-n-octoxyphenyl, 2-hydroxyphenyl, 4-((E)-ethen-2-yl salicylate)phenyl, 3-(diethylamino)phenyl, 4-n-hexoxyphenyl, 4-biphenyl, 4-naphthyl, 4-carboxyethylphenyl, or (E)-ethen-2-yl phenyl.

[0290] Exemplary compounds that may be included in the composition include, without limitation:

[0291]

[0292]

[0293]

[0294]

[0295] Also encompassed are the stereoisomers of the above compounds in particular the Z isomers, if the E isomer is shown, and vice versa.

[0296] A preferred compound to be used in these compositions is any one of:

[0297]

[0298] In various embodiments, the compound(s) included in said composition has a biodegradability of at least 10%, at least 20%, at least 30%, at least 40%, at least 50%, at least 60%, at least 65%, at least 70%, at least 75%, at least 80%, at least 85% or at least 90% degradation as determined over 28 days at 22°C according to OECD 301F.

[0299] The composition may be a personal care, pharmaceutical or home care composition. Depending on the intended use, it may further comprise at least one of the following components: UV filters different from the compounds of formula (I), emulsifiers, emollients, thickeners, cosmetic oils, sensory enhancers, consistency agents, film forming agents, UV performance boosters, preservatives, and perfumes. Examples of such components are disclosed in more detail below.

[0300] Similar to the compounds of formula (I), the at least one other component preferably also has a biodegradability of at least 20%, at least 30%, at least 40%, at least 50%, at least 60%, at least 65%, at least 70%, at least 75%, at least 80%, at least 85% or at least 90% degradation as determined over 28 days at 22°C according to OECD 301F.

[0301] In various embodiments, it may be preferred that essentially all or all organic components of the composition have a biodegradability of at least 20%, at least 30%, at least 40%, at least 50%, at least 60%, at least 65%, at least 70%, at least 75%, at least 80%, at least 85% or at least 90% degradation as determined over 28 days at 22°C according to OECD 301F. In some embodiments, this may also apply to the total composition. “Essentially all”, as used herein in this context, refers to at least 70 wt.-% of the totality of the indicated components, preferably at least 75%, at least 80%, at least 85%, or at least 90% by weight relative to the total weight of the composition.

[0302] Depending on the type of composition, all above listed components may be pharmaceutically, cosmetically and / or dermatologically acceptable.

[0303] Preferably, the compound of formula (I) is present in the composition, in particular a pharmaceutical or personal care composition as described herein, in an amount of from 0.5 to 50 wt.-%, 1 to 45 wt.-%, 2 to 40 wt.-%, 2.5 to 35 wt.-%, 1.0 to 20 wt.-%, 1.0 to 15 wt.-%, 1.0 to 10.0 wt.-%, 1.5 to 8 wt.-%, or 2.0 to 6.0 wt.-%, based on the total weight of the personal care or pharmaceutical composition. Lower concentration limits may be 0.5, 1.0, or 1.5 wt.-% and upper limits may be 50, 45, 40, 35, 30, 25, 20, 19, 18, 17, 16, 15, 14, 13, 12, 11, 10, 9, 8, 7,,6, 5 or 4 wt.-%. All amounts are given relative to the total weight of the composition.

[0304] In various embodiments, the above compositions, preferably pharmaceutical or personal care compositions further comprise at least one further UV filter different to the compounds of formula (I).

[0305] This additional UV filter may be selected from organic and inorganic UV filters and may optionally be biodegradable, as defined above. In various embodiments, such additional UV filter is selected from inorganic UV filters. In various embodiments, it may be selected from organic UV filters. The additional UV filter may be a particulate or oil-soluble or water-soluble UV filter. Water soluble UV filters have a solubility in water of at least 2 % by weight, preferably at least 3 % by weight, more preferably at least 5 % by weight. If no indicated otherwise, all solubilities given herein are at standard conditions, i.e. room temperature (25°C) and atmospheric pressure (1013 mbar).

[0306] “Oil soluble” UV filters or “UV filters soluble in at least one cosmetic oil” have a solubility in common cosmetic oils, such as C₁₂-C₁₅-alkyl benzoate, dibutyl adipate, diisopropyl sebacate, phenethyl benzoate, coco-caprylate ( / caprate), propylheptyl caprylate, caprylic / capric triglyceride, cocoglycerides, propylene glycol dicaprylate / dicaprate, butylene glycol dicaprylate / dicaprate, triethyl citrate, isopropyl myristate, isopropyl palmitate, lauryl lactate, phenox, ethyl caprylate isopropyl lauroyl sarcosinate or dicaprylyl carbonate of at least 2 % by weight, preferably at least 5 % by weight, more preferably at least 7 % by weight.

[0307] If a UV filter is defined as being “oil-soluble” or “soluble in at least one cosmetic oil” herein, this means that it has a solubility of at least 2% by weight in any one or more of the afore-mentioned cosmetic oils, i.e. in one or more of C₁₂-C₁₅-alkyl benzoate, dibutyl adipate, diisopropyl sebacate, phenethyl benzoate, coco-caprylate ( / caprate), propylheptyl caprylate, caprylic / capric triglyceride, cocoglycerides, propylene glycol dicaprylate / dicaprate, butylene glycol dicaprylate / dicaprate, triethyl citrate, isopropyl myristate, isopropyl palmitate, lauryl lactate, phenox, ethyl caprylate isopropyl lauroyl sarcosinate, and dicaprylyl carbonate. In some embodiments, it may have the given solubility in all of the listed cosmetic oils.

[0308] The term insoluble, particulate organic UV filter refers to UV filters that are not soluble in water and not in cosmetic oils. This may mean that their solubility in water and the cosmetic oils mentioned above is below 2 % by weight, for example below 1 % by weight.

[0309] As the at least one additional UV filter, UVA, UVB, and / or different broadband UV filters may be used. Suitable UV filters may be organic or inorganic, particulate or non-particulate. Non-particulate UV filters may be miscible or soluble in a given solvent, such as water or a cosmetic oil. In some instances, they may be water soluble or oil soluble, as herein defined. In contrast to non-particulate UV filters, the term “particulate UV filter” relates to UV filters that are essentially insoluble in water or (cosmetic) oils, i.e. their solubility in water and the cosmetic oils mentioned above is below 2 % by weight, for example below 1 % by weight. The term “organic particulate UV filter” relates to UV filters that can be micronized due to their low water and low oil solubility and are dispersed as a particle in water or in oil. “Non-particulate” thus means those filters that are oil- and / or water miscible or -soluble. Oil- and / or water-soluble filters as defined herein, i.e. are not present as solids in the compositions, but may be solids (as such, i.e. if not formulated with other compounds) at 25°C.

[0310] In various embodiments, the UV filters to be additionally comprised in the compositions defined herein are UV filters that are solid at 25 °C and / or are soluble in at least one cosmetic oil. In various embodiments, they are both, i.e. solid at 25°C and soluble in at least one cosmetic oil.

[0311] In various embodiments, the at least one additional UV filter comprised in the compositions of the invention comprises or is a non-particulate oil-soluble UV filter. In various embodiments, the at least one additional UV filter comprised in the compositions of the invention comprises or is a non-particulate water-soluble UV filter.

[0312] In various embodiments, the at least one additional UV filter comprised in the compositions of the invention comprises or is a particulate UV filter.

[0313] The at least one additional UV filter comprises or is, in various embodiments, an organic UV filter.

[0314] In various embodiments, the at least one additional UV filter comprises an organic, solid and oil-soluble UV filter. In various alternative or cumulative embodiments, the at least one additional UV filter comprises an organic, solid and particulate UV filter.

[0315] The compositions of the invention may comprise any one or more of the above types of additional UV filter either individually or in combination.

[0316] Suitable UVA filters may be selected from the group consisting of disodium phenyl dibenzimidazole tetrasulfonate, hexyl 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoate (INCI diethylamino hydroxybenzoyl hexyl benzoate), 1-(4-(1,1-dimethylethyl)phenyl)-3-(4-methoxyphenyl)propane-1,3-dione (INCI butyl methoxydibenzoylmethane, also known as avobenzone), terephthalylidene dicamphor sulfonic acid (TDSA), methoxypropylamino cyclohexenylidene ethoxyethylcyanoacetate (MCE), and combinations thereof.

[0317] Suitable UVB filters may be selected from the group consisting of 4,4',4"-(1,3,5-triazine-2,4,6-triyltriimino)tris-benzoic acid-tris(2-ethylhexyl)ester (INCI ethylhexyl triazone), 4,4'-[[6-[[4-[[(1, 1 -dimethylethyl)amino]carbonyl]phenyl]amino]-1,3,5-triazin-2,4-diyl]diimino]bis-benzoic acid-bis(2-ethylhexyl)ester (INCI diethylhexyl butamido triazone), phenylbenzimidazole sulfonic acid, and combinations thereof.

[0318] Suitable broadband UV filters may be selected from the group consisting of bis-ethylhexyloxyphenol methoxyphenyl triazine (INCI bis-ethylhexyloxyphenol methoxyphenyl triazine), 2-(2H-benzotriazol-2-yl)-6-[(2-ethylhexyloxy)methyl]-4-methylphenol, 2-(2H-benzotriazol-2-yl)-4-methyl-6-[2-methyl-3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]-1-disiloxanyl]propyl]phenol (INCI drometrizole trisiloxane), 2,2'-methylenbis[6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol] (INCI methylene Bis-benzotriazolyl tetramethylbutylphenol), phenylene bis-diphenyltriazine (PBDT), benzophenone-3 and combinations thereof.

[0319] Suitable organic particulate UV filters ( / .e., insoluble, organic UV filters) may be selected from the group consisting of 2,2'-methylene bis[6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol] (INCI methylene bis-benzotriazolyl tetramethylbutylphenol), 2,4,6-tris(biphenyl-4-yl)-1,3,5-triazine (INCI trisbiphenyl triazine), 1,1’-(1,4-piperazinediyl)bis[1-[2-[4-(diethylamino)-2-hydroxybenzoyl]phenyl]-methanone (INCI bis-(diethylaminohydroxybenzoyl benzoyl) piperazine), 5,6,5’,6’-tetraphenyl-3-3’-(1,4-phenylene)bis(1,2,4-triazine) (INCI phenylene bis-diphenyltriazine; PBDT), 1,4-di(benzoxazole-2'- yl)benzene and combinations thereof. Further examples of suitable organic particulate UV filters are described e.g. in WO9703643, W02009077356 and WO2015155158. Preferably, the particulate UV filters have a particle size DN50 determined by light scattering of less than 2000 nm, preferably less than 1000 nm, wherein DN50 refers to the particle size value, where half of the population lies below this value, and half of the population lies above this value, i.e., the median value of the particle size volume distribution.

[0320] Inorganic UV filters include titanium dioxide, zinc oxide, iron oxide, cerium oxide and mixtures thereof. In various embodiments, the inorganic UV filters may be applied as a nano material. In this connection it is to be understood that the term “nano material” follows the recommendation of the European Commission 2011 / 696 / EU. Accordingly, in a nano material 50 % of particles, based on a number-based size distribution, are smaller than 100 nm, including constituent particles in aggregates or agglomerates. In another embodiment of the present invention, the inorganic UV filters may be applied as a non-nano material. Accordingly, in a non-nano material more than 50 % of the particles, based on a number-based size distribution, are larger than 100 nm. It is also possible to use mixtures of nano and non-nano inorganic UV filters. Furthermore, the inorganic UV filters may be coated or uncoated. If present, titanium dioxide is preferably coated, as uncoated titanium dioxide is photocatalytic and should be avoided in sunscreens. Coatings suitable in the context of inorganic UV filters may be organic and / or inorganic and are, for instance, disclosed in WO 2023 / 036749 A1.

[0321] In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), bis-ethylhexyloxyphenol methoxyphenyl triazine (BEMT).

[0322] In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), diethylamino hydroxy benzoyl hexyl benzoate (DHHB).

[0323] In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), butyl methoxydibenzoylmethane (BMDBM).

[0324] In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), ethylhexyl triazone (EHT).

[0325] In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), methylene bis-benzotriazolyl tetramethylbutylphenol (MBBT).

[0326] In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), tris-biphenyl triazine (TBPT).

[0327] In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), methoxypropylamino cyclohexenylidene ethoxyethylcyanoacetate (MCE).

[0328] In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), zinc oxide. In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), titanium dioxide.

[0329] In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), cerium oxide.

[0330] In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), iron oxide.

[0331] In various embodiments, the composition is free of octocrylene.

[0332] In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), at least one UVA filter, such as DHHB or BMDBM or MCE, and at least one UVB filter, such as EHT.

[0333] In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), at least one broadband UV filter, such as BEMT, and at least one UVA filter, such as DHHB or BMDBM or MCE.

[0334] In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), at least one broadband UV filter, such as BEMT, and at least one UVB filter, such as EHT.

[0335] In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), at least one broadband UV filter, such as BEMT, and at least one UVA filter, such as DHHB or BMDBM or MCE, and at least one UVB filter, such as EHT.

[0336] In various embodiments, the composition comprises at least one broadband UV filter, such as BEMT, and at least one UVA filter, such as DHHB, and at least one UVB filter, such as EHT.

[0337] In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), at least one particulate UV filter, such as MBBT, PBDT or TBPT, and at least one UVA filter, UVB filter and / or broadband UV filter, such as any one or more of DHHB, BMDBM, MCE, EHT, and BEMT. The composition may thus comprise combinations of MBBT and BEMT, MBBT and EHT, and MBBT and DHHB or BMDBM or MCE. Further, a particulate UV filter, such as MBBT, may be used in combination with any combination of UVA, UVB and broadband UV filters disclosed in various embodiments above.

[0338] In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), at least one broadband UV filter, such as BEMT, preferably in an amount of from 0.5 to 10 % by weight, such as 0.5, 0.6, 0.7, 0.8, 0.9, 1.0, 1.5, 2.0, 2.5, 3.0, 3.5, 4.0, 4.5, 5.0, 6, 7, 8, 9, or 10 wt.-%, more preferably in an amount of from 2 to 5 % by weight, based on the total weight of the sunscreen or daily care composition. In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), at least one UVA filter, such as DHHB or BMDBM or MCE, preferably in an amount of from 0.5 to 10 % by weight, such as 0.5, 0.6, 0.7, 0.8, 0.9, 1.0, 1.5, 2.0, 2.5, 3.0, 3.5, 4.0, 4.5, 5.0, 6, 7, 8, 9, or 10 wt.-%, based on the total weight of the sunscreen or daily care composition.

[0339] In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), at least one UVB filter, such as EHT, preferably in an amount of from 0.5 to 10 % by weight, such as 0.5, 0.6, 0.7, 0.8, 0.9, 1.0, 1.5, 2.0, 2.5, 3.0, 3.5, 4.0, 4.5, 5.0, 6, 7, 8, 9, or 10 wt.-%, based on the total weight of the sunscreen or daily care composition.

[0340] In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), at least one particulate UV filter, such as MBBT, PBDT, orTBPT, preferably in an amount of from 0.5 to 10 % by weight, such as 0.5, 0.6, 0.7, 0.8, 0.9, 1.0, 1.5, 2.0, 2.5, 3.0, 3.5, 4.0, 4.5, 5.0, 6, 7, 8, 9, or 10 wt.-%, based on the total weight of the sunscreen or daily care composition.

[0341] In various embodiments, the weight ratio of the at least one broadband UV filter to at least one UVB filter, at least one UVA filter or at least one particulate UV filter may be in the range of 1:5 to 5:1, for example 1:3 to 3:1.

[0342] In various embodiments, the weight ratio of the at least one UVA filter to at least one UVB filter or at least one particulate UV filter may be in the range of 1:5 to 5:1, for example 1:3 to 3:1.

[0343] In various embodiments, the weight ratio of the at least one UVB filter to at least one particulate UV filter may be in the range of 1:5 to 5:1, for example 1:3 to 3:1.

[0344] In various embodiments, the weight ratio of the at least one particulate UV filter to at least one UVB filter or at least one UVA filter may be in the range of 1:5 to 5:1, for example 1:3 to 3:1.

[0345] In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), ethylhexyl methoxycinnamate.

[0346] In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), ethylhexyl salicylate.

[0347] In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), homosalate.

[0348] In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), amiloxate.

[0349] In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), padimate O. In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), shinorine.

[0350] In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), gadusol.

[0351] In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), mycosporine-2 glycine.

[0352] In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), porphyra-334.

[0353] In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), a UV filter from the group of cyanoacrylates, the cyanoacrylates optionally being any one or more of

[0354]

[0355] In various embodiments, the composition comprises, in addition to the at least one UV filter of formula (I), at least one compound selected from those listed in the following table:

[0356]

[0357]

[0358]

[0359] All documents cited herein above in relation to the additional UV filters that may be included in the compositions of the invention, are herewith incorporated by reference in their entirety.

[0360] In one embodiment of the present invention, the composition further comprises at least two additional UV filters, different to the compound of formula (I). These may be selected from those described above.

[0361] In various embodiments, the additional UV filter may be a natural and / or biodegradable UV filter. “Natural”, as used in this context, refers to compounds that occur in nature and are thus naturally occurring compounds in contrast to those that are artificially produced. “Biodegradable”, as used in this context, refers to compounds that are biodegradable as defined herein above. In various embodiments, the composition comprises a total of 5 to 40 wt.-%, such as 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, or 40 wt.-% of UV filters, preferably of 8 to 35 wt.-%, more preferably of 9 to 30 wt.-% or of 9 to 35 wt.-%, still more preferably of 9 to 25 wt.-%, and in particular of 9 to 20 wt.-%, based on the total weight of the sunscreen or daily care composition.

[0362] In one embodiment of the present invention, the composition according to the present invention further comprising a photostabilizer. Photostabilizers may be used in a quantity sufficient to obtain a substantial and significant improvement in the photostability of the composition containing a compound of formula (I). This minimum quantity of photostabilizer to be used may vary depending on the starting quantity of compound of formula (I) present in the composition and depending on the nature of the dermatologically acceptable support used in the composition. It may be determined without difficulty using a conventional photostability measuring test.

[0363] In various embodiments, the photostabilizer is present in the composition in an amount of at least 0.5 wt.-%, preferably at least 1 wt.-%, more preferably at least 2 wt.-%, and in particular at least 4 wt.-%, based on the total weight of the composition. In another preferred embodiment, the photostabilizer is present in the composition in an amount of from 0.5 to 15 wt.-%, preferably from 1 to 12 wt.-%, more preferably from 2 to 10 wt.-%, and in particular from 4 to 8 wt.-%, based on the total weight of the composition.

[0364] In various embodiments, the photostabilizer is a quencher. The quencher may be present in the composition in an amount of at least 0.5 wt.-%, preferably at least 1 wt.-%, more preferably at least 1.5 wt.-%, and in particular at least 2 wt.-%, based on the total weight of the composition. In another embodiment, the quencher is present in the composition in an amount of from 0.5 to 10 wt.-%, preferably from 1 to 8 wt.-%, more preferably from 1.5 to 6 wt.-%, and in particular from 2 to 5 wt.-%, based on the total weight of the composition.

[0365] In a preferred embodiment of the present invention, the photostabilizer is selected from the group consisting of

[0366] • CAS-Regno. 444811-29-4, Propanedioic acid, [(4-hydroxy-3,5-dimethoxyphenyl)methylene]-, bis(2-ethylhexyl) ester (Oxynex ST)

[0367] CAS-Regno. 477844-93-2, Octofluorene

[0368] 2-phenylethylbenzoate

[0369] CAS-Regno. 127474-91-3, 2,6-Naphthalenedicarboxylic acid, bis(2-ethylhexyl) ester (Hallbrite TQ, Corapan TQ)

[0370] ethylhexyl methoxycrylene

[0371] polyester-8

[0372] diethylhexyl syringylidenemalonate

[0373] trimethoxybenzylidene pentanedione

[0374] Bis(Cyano Butylacetate) Anthracenediylidene

[0375] polyester-25

[0376] butyloctyl salicylate CAS-Regno. 68890-66-4, Octopirox

[0377] Tinogard TT (INCI Tetradibutyl Pentaerithrityl Hydroxy- hydrocinnamate)

[0378] Tinogard HS (INCI Sodium Benzotriazolyl Butylphenol Sulfonate)

[0379] Tinogard TL (INCI Benzotriazolyl Dodecyl p-Cresol)

[0380] Phenol, 2-(2H-benzotriazol-2-yl)-6-dodecyl-4-methyl-, branched and linear

[0381] Cibafast H Liquid (INCI Sodium Benzotriazolyl Butylphenol Sulfonate, Buteth-3, Tributyl Citrate) Tinogard AS (INCI Bumetrizole)

[0382] Tris(tetramethylhydroxypiperidinol) citrate (Tinogard Q)

[0383] Piperidinol, 1 -hydroxy-2, 2, 6, 6-tetramethyl-, 2-hydroxy-1,2,3-propanetricarboxylate (3:1) (salt) CAS-Regno. 1750-49-8, N-(2-Hydroxypropyl)urea

[0384] CAS-Regno. 2078-71-9, N-(2-Hydroxyethyl)urea

[0385] mixture of n-butylphthalimide and isopropylphthalimide

[0386] CAS-Regno. 872424-70-9

[0387] CAS-Regno. 872424-71-0

[0388] CAS-Regno. 872424-72-1

[0389] CAS-Regno. 872424-73-2

[0390] CAS-Regno.6197-30-4, Octocrylene

[0391] CAS-Regno. 118-60-5, 2-Ethylhexyl salicylate

[0392] CAS-Regno. 180898-37-7, Disodium phenyldibenzimidazoletetrasulfonate Neo Heliopan AP or NeoHeliopan APC

[0393] CAS-Regno. 302776-68-7, Uvinul A Plus

[0394] CAS-Regno.70356-09-1, 4-tert-Butyl-4'-methoxydibenzoylmethane (Avobenzone)

[0395] Tinosorb M (micronized CAS-Regno. 103597-45-1)

[0396] Tinosorb S (CAS-Regno. 187393-00-6)

[0397] CAS-Regno. 88122-99-0, Ethylhexyl triazone (Octyl triazone; Uvinul T 150)

[0398] CAS-Regno. 154702-15-5, Diethylhexyl butamidotriazone (Uvasorb HEB)

[0399] CAS-Regno. 155633-54-8, Drometrizole trisiloxane (Mexoryl XL), and

[0400] • CAS-Regno. 92761-26-7 Mexoryl SX; Terephthalylidene-3,3'-dicamphor-10,10'-disulfonic acid

[0401] Specific examples include triplet quenchers, such as Tinogard Q (comprising tris(tetramethylhydroxypiperidinol) citrate (also known as 4-Piperidinol, 1 -hydroxy-2, 2, 6, 6-tetramethyl-, 2-hydroxy-1,2,3-propanetricarboxylate (3:1) (salt) or CAS-Regno. 220410-74-2), water (CAS-Regno. 7732-18-5) and ethanol (CAS-Regno. 64-17-5)). Tinogard Q is an Excited State Quencher, water soluble and is delivered in liquid formulation. Excited State Quencher helps to prevent light induced degradation of formulations in transparent packagings. In combination with UV absorbers it results in highly effective stabilizer systems. In general, Tinogard Q is used to protect personal care products from degradation caused by exposure to UV radiation in transparent packaging. It is applied in e.g. body wash, face wash, liquid hand soap, skin care, shampoo, hair conditioner, and fragrances.

[0402] In various embodiments, the compositions can additionally comprise one or more further biodegradable compounds, including those selected from the group consisting of C12-C15alkyl benzoates, coco glycerides, coconut oil, dibutyl adipate, dodecyl lactate, ethylhexyl benzoate, glycerol, glyceryl stearate, lauryl glycoside, lauryl lactate, triglycerides, phenoxyethanol, phenoxy ethyl caprylate, polyglyceryl-2-dipolyhydroxy-stearate, stearoyl glutamate and salts thereof, stearyl alcohol, dicarboxymethyl alaninate and salts thereof, and xanthan gum as well as combinations thereof. The salts of the afore-mentioned compounds may be the alkaline metal salts, for example the sodium salts.

[0403] In some embodiments, the composition is free of at least one or more of parabenes and octocrylene. In some embodiments, the composition is free of parabens. In various embodiments, the composition is free of octocrylene. In various embodiments, the composition is free of parabenes and octocrylene.

[0404] In various embodiments, the composition, for example a sunscreen or daily care composition with photoprotection, provides a SPF of more than 15, preferably of more than 30. In another preferred embodiment of the present invention, the composition provides a SPF of more than 50, preferably of more than 60. In another preferred embodiment of the present invention, the composition provides a SPF of more than 90. The SPF may be determined according to any method known in the art.

[0405] Further, in connection with the above embodiments, it is to be understood that the compositions may comprise at least one further additive.

[0406] In one embodiment, the at least one additive is selected from the group consisting of cosmetic oils, emulsifiers, emollients, viscosity regulators (thickeners), stabilizers, sensory enhancers, humectants, film formers, UV scattering compounds, UV boosters, pH adjusters, adjuvants such as vitamins, antioxidants, chelating agents, preservatives, perfumes, and combinations thereof, including those mentioned above as being biodegradable.

[0407] Exemplary cosmetic oils include, without limitation, C12-C15-alkyl benzoate, dibutyl adipate, diisopropyl sebacate, phenethyl benzoate, coco-caprylate ( / caprate), propylheptyl caprylate, caprylic / capric triglyceride, cocoglycerides, propylene glycol dicaprylate / dicaprate, butylene glycol dicaprylate / dicaprate, triethyl citrate, isopropyl myristate, isopropyl palmitate, phenox, ethyl caprylate isopropyl lauroyl sarcosinate, and dicaprylyl carbonate

[0408] Exemplary O / W emulsifiers include, without limitation,

[0409] glucose derivatives such as cetearyl glucoside, arachidyl glucoside, lauryl glucoside, polyglyceryl-3 methylglucose distearate, methyl glucose sesquistearate;

[0410] sucrose derivative such as sucrose polystearate, sucrose palmitate;

[0411] sorbitol derivatives such as polysorbate derivatives;

[0412] inulin derivatives such as inulin lauryl carbamate;

[0413] glycerides of fatty acids such as glyceryl stearate, glyceryl stearate SE, glyceryl stearate citrate, glutamic acid derivatives such as sodium stearoyl glutamate;

[0414] sulfosuccinic acid derivatives such as disodium cetearyl sulfosuccinate;

[0415] phosphoric acid derivatives such as potassium cetyl phosphate, ceteh-10 phosphate, C20-22 alkyl phosphate; fatty acid esters of polyglyceryl such as polyglyceryl-3-diisostearate, polyglyceryl-2- dipolyhydroxystearate; polyglyceryl-10 stearate

[0416] oxyalkenylated fatty alcohol such as ceteareth-20, steareth-21, beneheth-25

[0417] oxyalkenylated fatty acid such as PEG-100 stearate

[0418] oxyalkenylated organomodified silicone / polysiloxane / polyalkyl / polyether copolymers and derivatives.

[0419] ethoxylated fatty acid soap

[0420] phospholipids based such as lecithin derivatives

[0421] Exemplary emulsifiers to form a W / O emulsion include, without limitation,

[0422] glycerides of fatty acids such glyceryl oleate, sorbitan laurate

[0423] sorbitan esters such as sorbitan oleate

[0424] fatty acid esters of polyglyceryl such as polyglyceryl-3-diisostearate, polyglyceryl-2- dipolyhydroxystearate, polyglyceryl-4 isostearate

[0425] Oxyalkenylated fatty alcohol such steareth-2

[0426] Oxyalkenylated fatty acid such as PEG-30 dipolyhydroxystearate

[0427] organomodified silicone / polysiloxane / polyalkyl / polyether copolymers and derivatives such as cetyl dimethicone copolyol, cetyl PEG / PPG-10 / 1 Dimethicone, PEG-10 dimethicone

[0428] Exemplary emollients include, without limitation,

[0429] esters of linear or branched fatty acids with linear or branched fatty alcohols such as propylheptyl caprylate, coco caprylate, isopropyl myristate, ethylhexyl palmitate;

[0430] esters of aromatic carboxylic acids with linear or branched fatty alcohols such as C12-C15-alkyl benzoate, ethylhexyl benzoate, phenethyl benzoate;

[0431] dicarboxylic acid esters with linear or branched alcohols such as dibutyl adipate, dicaprylyl carbonate, diisopropyl sebacate;

[0432] esters of hydroxycarboxylic acids with linear or branched fatty alcohols;

[0433] esters of linear or branched fatty acids with polyhydric alcohol such as butylene glycol dicaprylate / dicaprate;

[0434] mono-, di-, tri-glycerides based on C6-C18 fatty acids such as caprylic I capric triglycerides, coco glycerides;

[0435] guerbet alcohols such as octyldodecynol;

[0436] hydrocarbons such as hydrogenated polyisobutene, mineral oil, squalene, isohexadecane; ethers such as dicaprylyl ether;

[0437] silicone derivatives (organomodified polysiloxanes) such as dimethylpolysiloxane, cyclic silicones.

[0438] Exemplary lipophilic thickeners include, without limitation,

[0439] fatty alcohols such as cetyl alcohol, cetearyl alcohol, stearyl alcohol; behenyl alcohol

[0440] fatty acids such as stearic acid; palmitic acid

[0441] fatty acid esters such as myristyl stearate, pentaerythrityl distearate, cetyl palmitate; Tribehenin, dextrin palmitate waxes such as beeswax, carnauba wax, microcrystalline wax, ceresin, ozocerite; Oryza Sativa bran wax, sunflower wax

[0442] hydrogenated vegetable oil, hydrogenated castor oil, hydrogenated vegetable glycerides, hydrogenated castor oil / sebacic acid copolymer

[0443] silica based derivatives such as silica, silica dimethyl silylate.

[0444] Hydrophilic stabilizers / thickeners include, without limitation,

[0445] natural gums such as xanthan gum, tara gum, carrageenan, guar gum, agar gum, alginates, gellan gum

[0446] silicate derivatives such as magnesium aluminum silicates;

[0447] cellulose derivatives such as hydroxypropyl cellulose, microcrystalline cellulose

[0448] starch derivatives such as hydroxypropyl starch phosphate

[0449] polyacrylates or homopolymers of reticulated acrylic acids or polyacrylamides such as carbomers, acrylate copolymers, acrylate I C10-C30-alkyl acrylate crosspolymer, acrylate I beheneth-25 methacrylate copolymer

[0450] Also included may be UV protection scattering compounds. These include, without limitation:

[0451] microcrystalline cellulose;

[0452] calcium carbonate;

[0453] hydroxyapatite;

[0454] silica.

[0455] hollow sphere such as Styrene / Acrylates Copolymer

[0456] Further components may belong to the class of film formers and film forming enhancers. Such compounds include, without limitation,

[0457] hydrogenated dimer dilinoleyl / dimethylcarbonate copolymer;

[0458] diisostearoyl polyglyceryl-3 dimer dilinoleate;

[0459] polyglyceryl-3 stearate / sebacate crosspolymer;

[0460] cellulose derivatives, such as methylcellulose and ethylcellulose;

[0461] capryloyl glycerin / sebacic acid copolymer.

[0462] Exemplary sensory enhancers include, without limitation,

[0463] polyamide derivatives such as nylon-12;

[0464] polymethyl methacrylates;

[0465] silica;

[0466] mica;

[0467] polymethylsilsesquioxane;

[0468] polyethylene;

[0469] starch derivatives such as aluminum starch octenylsuccinate;

[0470] dimethicone derivatives;

[0471] boron nitride; HDI / trimethylol hexyllactone crosspolymer;

[0472] perlite.

[0473] Exemplary humectants include, without limitation, polyols such as:

[0474] glycerin;

[0475] butylene glycol;

[0476] propylene glycol;

[0477] sorbitol

[0478] beta-glucan;

[0479] 1,2 pentadiol;

[0480] 1,2 hexandiol;

[0481] 1,2 octandiol;

[0482] 1,2 decandiol;

[0483] 2-Methyl-1,3-propandiol.

[0484] Exemplary adjuvants include, without limitation,

[0485] ethanol

[0486] dyes

[0487] pigments such as iron oxides

[0488] tocopherol derivatives;

[0489] retinol derivatives;

[0490] ascorbic acid derivatives;

[0491] bisabolol;

[0492] allantoin;

[0493] panthenol;

[0494] chelating agents (EDTA, EDDS, EGTA, phytic acid, piroctone olamine);

[0495] ethylhexyl glycerin;

[0496] hydroxyacetophenone;

[0497] caprylhydroxymic acid;

[0498] propellants such as propane, butane, isobutene, dimethyl ether;

[0499] styrene I PVP or styrene acrylamide copolymers;

[0500] insect repellants such as butylacetylaminopropionate.

[0501] Exemplary preservatives include, without limitation,

[0502] benzyl alcohol;

[0503] zingerone.

[0504] Exemplary perfumes include, without limitation, those selected from the group consisting of limonene, citral, linalool, alpha-isomethylionon, geraniol, citronellol, 2-isobutyl-4-hydroxy-4-methyltetrahydropyrane, 2-tert.-pentylcyclohexylacetate, 3-methyl-5-phenyl-1 -pentanol, 7-acetyl-1,1,3,4,4,6-hexamethyltetraline, adipine acid diester, alpha-amylcinnamaldehyde, alpha-methylionon, amyl C butylphenylmehtylpropionalcinnamal, amylsalicylate, amylcinnamylalcohol, anisalcohol, benzoin, benzylalcohol, benzylbenzoate, benzylcinnamate, benzylsalicylate, bergamot oil, bitter orange oil, butylphenylmethylpropioal, cardamom oil, cedrol, cinnamal, cinnamylalcohol, citronnellylmethylcrotonate, lemon oil, coumarin, diethylsuccinate, ethyllinalool, eugenol, evernia furfuracea extracte, evernia prunastri extracte, farensol, guajak wood oil, hexylcinnamal, hexylcalicylate, hydroxycitronellal, lavender oil, lemon oil, linaylacetate, mandarine oil, menthyl PCA, methylheptenone, nutmeg oil, rosemary oil, sweet orange oil, terpineol, tonka bean oil, triethylcitrate, vanillin and combinations thereof.

[0505] In connection with the above preferred embodiments, it is to be understood that if the composition comprises two or more additives, combinations of the additives as defined above are also part of the invention.

[0506] The final formulations of the compositions may exist in a wide variety of presentation forms, for example: in the form of liquid preparations as a W / O, O / W, oil-in-water-in-oil (O / W / O), water-in-oil-in water (W / O / W), a bi-phasic formulation or phase-inversion-technology (PIT) emulsion, a polymeric-based emulsion, and all kinds of microemulsions. The final formulations can be provided in different forms such as a gel, a cream, milk or lotion, in the form of a powder, in the form of a stick, in the form of a spray (spray with propellant gas or pump-action spray) or an aerosol, in the form of a foam, or in the form of a paste.

[0507] Typically, composition may comprise water in an amount of more than 5 % by weight, such as within the range of about 5.5 to 95 wt.-%, such as within the range of 10 to 90 wt.-%, for instance within the range of 15 to 85 wt.-%, based on the total weight of the composition.

[0508] For instance, when formulated as a water-in oil or an oil-in-water dispersion, an optional cosmetically acceptable carrier preferably comprises 5 to 50 % of an oil phase, 1 to 10 % of an emulsifier and 30 to 90 % of water, each by weight based on the total weight of the carrier. The oil phase may comprise any oil conventionally used in cosmetic formulations.

[0509] In connection with the above embodiments, it is to be understood that the compositions disclosed herein, in particular the sunscreen or daily care compositions, are particularly suitable for protection of the skin from UV radiation.

[0510] Hence, the present invention further relates to the composition, as defined herein, for use in protecting the human skin from UV radiation. The present invention further relates to a method of protecting the human skin from UV radiation by administration of the composition, such as the sunscreen or daily care composition, as defined herein.

[0511] The invention is further directed to the use of the compounds described herein above, namely those of formula (I), to as an organic UV filter in a pharmaceutical, personal care or home care composition.

[0512] Also encompassed is the use of these compounds as a light stabilizer to protect ingredients against photolytic degradation, in particular in home care and industrial and institutional cleaning compositions. The invention thus also features methods for protecting ingredients of a composition against photolytic degradation by adding a compound of formula (I) to said composition.

[0513] It is to be understood that the above embodiments of the compounds and compositions are also applicable for the uses and methods according to the present invention, and vice versa.

[0514] The present invention is further illustrated by the following non-limiting examples. Examples

[0515] Example 1: Syntheses of the compounds

[0516]

[0517]

[0518] General procedure compound 1

[0519] 2-Hydroxy acetophenone (1.0 eq) and benzaldehyde (1,1eq) were dissolved in tetrahydrofuran, aqueous NaOH (2.2 eq) was added at 25°C. The light-yellow slurry was heated to 50°C for 7

[0520] hours and a thick orange slurry was observed. HPLC of reaction mass showed desired product of about 85%. The orange slurry was cooled to 20°C and acidified with dilute HCI where after acidification the solid get dissolved in tetra hydrofuran. The aqueous layer was removed, and the organic layer was washed with saturated aqueous NaCI solution. The organic layer was dried over Na2SO4, and the solvent was evaporated under reduced pressure giving crude as an orange viscous mass which was poured in stirred isopropanol, and a yellow solid was precipitated. The solid was filtered and washed with isopropanol. The yellow solid was well dried under vacuum to

[0521] obtain a product with 70% yield.

[0522] 1H NMR (300 MHz, DMSO-d6) 6 12.50 (s, 1H), 8.27 (dd, J = 8.2, 1.6 Hz, 1H), 8.06 (d, J = 15.6 Hz, 1 H), 7.99 - 7.88 (m, 2H), 7.85 (d, J = 15.6 Hz, 1 H), 7.58 (ddd, J = 8.7, 7.1, 1.6 Hz, 1 H), 7.54 - 7.45 (m, 3H), 7.02 (ddd, J = 7.1, 3.5, 2.4 Hz, 2H).

[0523] General procedure compound 2

[0524] 2-Hydroxy 5-methyl acetophenone (1.0 eq) and 4-methoxy benzaldehyde (1,1eq) were dissolved in tetrahydrofuran, aqueous NaOH (2.2 eq) was added at 25°C. The light-yellow slurry was

[0525] heated to 50°C for 7 hours and a thick orange slurry was observed. HPLC of reaction mass

[0526] showed desired product of about 85%. The orange slurry was cooled to 20°C and acidified with dilute HCI where after acidification the solid get dissolved in tetrahydrofuran. The aqueous layer was removed, and the organic layer was washed with saturated aqueous NaCI solution. The organic layer was dried over Na2SO4, and the solvent was evaporated under reduced pressure giving crude as an orange viscous mass which was poured in stirred isopropanol, and a yellow solid was precipitated. The solid was filtered and washed with isopropanol. The yellow solid was well dried under vacuum I obtained a product with 75% yield.

[0527] 1H NMR (500 MHz, DMSO-d6) 612.58 (s, 1H), 8.11 -8.07 (m, 1H), 7.96 - 7.87 (m, 3H), 7.83 (d, J = 15.4 Hz, 1H), 7.37 (dd, J = 8.4, 2.1 Hz, 1H), 7.07 - 7.01 (m, 2H), 6.89 (d, J = 8.4 Hz, 1H), 3.84 (s, 3H), 2.33 (s, 3H).

[0528] NMR data of synthesized compounds according to general procedures

[0529] Compound 3

[0530] 1H NMR (300 MHz, DMSO-d6) 512.76 (s, 1H), 8.29 - 8.26 (m, 1H), 7.99 - 7.82 (m, 4H), 7.59-7.48 (d, 1H), 7.05-6.99 (m, 4H), 3.84 (s, 3H).

[0531] Compound 5

[0532]

[0533] 1H NMR (300 MHz, DMSO-d6) 612.76 (s, 1H), 7.705 -7.662 (m, 4H), 7.028-6.999 (d, 2H), 6.148-6.128 (d, 2H), 3.899 (s, 3H), 3.819 (s, 6H).

[0534] Compound 6

[0535]

[0536] 1H NMR (300 MHz, DMSO-d6) 612.26 (s, 1H), 8.04 -7.74 (m, 4H), 7.79- 7.74 (d, 2H), 7.59-7.53 (m, 2H), 7.37-7.34 (m, 2H), 7.04-6.90 (m, 8H), 6.20 (s, 4H).

[0537] Compound 7

[0538]

[0539] 1H NMR (300 MHz, DMSO-d6) 69.94 (s, 1H), 7.92 (s, 1H), 7.61 - 7.37 (m, 7H), 7.13- 7.07 (m, 3H), 6.70 (s, 1H).

[0540] Compound 8

[0541]

[0542] 1 H NMR (300 MHz, DMSO-d6) 6 13.18 (s, 1 H), 8.29 - 8.26 (d, 1 H), 7.99 - 7.82 (d, 1 H), 7.59-7.48 (m, 1H), 7.20-7.13 (d,2H), 7.05-6.99 (m, 2H), 6.25 (s, 1H), 3.84 (s, 3H).

[0543] Example 2: Biodegradation

[0544] Biodegradation of the compounds was determined as follows:

[0545] OECD 301 F (BASF screening test): Biodegradation in wastewater was tested in triplicate using the OECD 301 F manometric respirometry method. OECD 301 F is an aerobic test that measures biodegradation of a sample by measuring the consumption of oxygen. To a measured volume of medium, 100 mg / L test substance (i.e. compound of formula (I)), which is the nominal sole source of carbon is added along with the inoculum (aerated sludge taken from Mannheim waste water treatment plant). This is stirred in a closed flask at a constant temperature of 22 °C for 28 days. The consumption of oxygen is determined by measuring the change in pressure in the apparatus using an OxiTopC. Evolved carbon dioxide is absorbed in a solution of sodium hydroxide. Nitrification inhibitors are added to the flask to prevent usage of oxygen due to nitrification. The amount of oxygen taken up by the microbial population during biodegradation of the test substance (corrected for uptake by blank inoculum, run in parallel) is expressed as a percentage of ThOD (theoretical oxygen demand, which is measured by the elemental analysis of the compound). A positive control Glucose / Glucosamine is run along with the test samples for each cabinet.

[0546] Biodegradation can then be calculated according to the following formula according to the OECD Guideline for the Testing of Chemicals, Section 3

[0547] BOD = (mg O2uptake by test substance – mg O2uptake by blank) / mg test substance in vessel

[0548] % degradation is calculated according to the following formula according to the OECD Guidelines for the Testing of Chemicals, Section 3:

[0549] % degradation = BOD / ThOD x 100

[0550] The results are shown in Table 2. Compounds used are shown in Table 3.

[0551] Table 2: Biodegradation

[0552]

[0553] Table 3: Compounds used for biodegradation experiment

[0554]

[0555] Table 4

[0556]

[0557] λ max = wavelength in nm at extinction maximum in the range 290-420nm e11 = extinction at λ max

Claims

Claims1. Compound of formula (I)or a salt, hydrate, tautomer or stereoisomer thereof;whereinR1, R2, and R6are H;R3is H or -O(C3-C10alkyl);R4is H or C1-C4 alkyl;R5is H or -O(C1-C4alkyl);R7and R8are selected from H and phenyl of formula (II), wherein at least one of R7and R8is not H,whereinR11, R13and R15are independently selected from H, C3-C10alkyl, and -O(C3-C10alkyl);R12and R14are independently selected from H, C3-C10 alkyl, -0(C3-Cio alkyl), and -N(C1-C4alkyl); wherein at least one of R11, R12, R13, R14and R15is not H; andwherein if R11, R12, R14and R15are H and R13is isopropyl or -O-isopropyl, R3is not H; and whereinif R12is -O(C6alkyl), R3, R4, R5, R11, R13, R14and R15are not all H;if R14is -O(C6alkyl), R3, R4, R5, R11, R12, R13, and R15are not all H; andif R15is -O(C6alkyl), R3, R4, R5, R11, R12, R13, and R14are not all H.

2. Compound of formula (I)or a salt, hydrate, tautomer or stereoisomer thereof;whereinR1, R2, and R6are H;R3is H or -O(C3-C10alkyl);R4is H or C1-C4 alkyl;R5is H or -O(C1-C4alkyl);R7and R8are selected from H, optionally substituted pyrrole, substituted furan, substituted benzofuran, optionally substituted indole,wherein at least one of R7and R8is not H;wherein pyrrole, furan, benzofuran or indole, if substituted, are substituted by one to three substituents selected from C1-C10 alkyl, and -0(Ci-Cio alkyl);wherein if one of R7and R8is optionally substituted indole or benzofuran and the other is H, R3is not H.

3. The compound of claim 1 or 2, wherein(1) R3is H, -O(2-ethylhexyl), -O(methyl), or-O(isopropyl) and R2, R4and R5are optionally H; (2) R4is H or methyl and R2, R3and R5are optionally H;(3) R5is H or methoxy and R2, R3and R4are optionally H;(4) R8is phenyl of formula (II), R11is -O(n-propyl), -O(n-pentyl), -O(n-octyl), or -O(2-ethylhexyl), and R12, R13, R14and R15are optionally H;(5) R8is phenyl of formula (II), R12is -O(n-propyl), -N(ethyl)2, and R11, R13, R14and R15are optionally H;(6) R8is phenyl of formula (II), R13is -O(isopropyl), -O(n-pentyl), -O(n-hexyl), or -0(2- ethylhexyl), and R11, R12, R14and R15are optionally H;(7) R8is phenyl of formula (II), R11and R12are -O(n-propyl) and R13, R14and R15are optionally H;(8) R8is phenyl of formula (II), R11and R13are -O(n-pentyl) and R12, R14and R15are optionally H;(9) R3and R5are -O(methyl) and R2and R4are optionally H; and / or(10) R8is 5-methyl-2-furanyl, 3-pyrrolyl, 2-benzofuranyl, or 3-indolyl..

4. The compound of any one of claims 1 to 3, wherein the compound is of formula (I), wherein (1) R8is phenyl, R13is -O(2-ethylhexyl) and R1, R2, R3, R4, R5, R6, R7, R11, R12, R14and R15are H;(2) R8is phenyl, R11is -O(2-ethylhexyl) and R1, R2, R3, R4, R5, R6, R7, R12, R13, R14and R15are H;(3) R8is phenyl, R3and R13are -O(2-ethylhexyl) and R1, R2, R4, R5, R6, R7, R11, R12, R14and R15are H;(4) R8is phenyl, R3is -O(2-ethylhexyl), R13is isopropyl, and R1, R2, R4, R5, R6, R7, R11, R12, R14and R15are H;(5) R8is phenyl, R3is -O(methyl), R11and R12are -O(n-propyl), and R1, R2, R4, R5, R6, R7, R13, R14and R15are H;(6) R8is phenyl, R11and R13are -O(n-pentyl), and R1, R2, R3, R4, R5, R6, R7, R12, R14and R15are H;(7) R8is phenyl, R11is -O(n-octyl) and R1, R2, R3, R4, R5, R6, R7, R12, R13, R14and R15are H; (8) R8is phenyl, R12is -N(ethyl)2and R1, R2, R3, R4, R5, R6, R7, R11, R13, R14and R15are H; (9) R8is phenyl, R3and R5are -O(methyl), R13is -O(n-hexyl), and R1, R2, R4, R6, R7, R11, R12, R14and R15are H;(10) R8is 5-methyl-2-furanyl, R4is methyl, and R1, R2, R3, R5, R6, and R7are H;(11) R8is 3-pyrrolyl, and R1, R2, R3, R4, R5, R6, and R7are H;(12) R8is 2-benzofuranyl, R3is -O(2-ethylhexyl), and R1, R2, R4, R5, R6, and R7are H;(13) R8is 2-benzofuranyl, R3is -O(isopropyl), and R1, R2, R4, R5, R6, and R7are H;(14) R8is 3-pyrrolyl, R3is -O(2-ethylhexyl), and R1, R2, R4, R5, R6, and R7are H; or(15) R8is 3-indolyl, R3is -O(2-ethylhexyl), and R1, R2, R4, R5, R6, and R7are H.

5. The compound of any one of claims 1 to 4, wherein the compound has a biodegradability of at least 20% degradation as determined over 28 days at 22°C according to OECD 301F.

6. Composition comprising(1) at least one compound according to any one of claims 1 to 5, and(2) at least one other component selected from the group consisting of: UV filters different from the compounds of formula (I), emulsifiers, emollients, thickeners, cosmetic oils, sensory enhancers, consistency agents, film forming agents, UV performance boosters, preservatives, and perfumes.

7. The composition of claim 6, wherein the composition further comprises at least one further UV filter different to the compounds of formula (I), preferably selected from(1) at least one UVA filter, preferably selected from the group consisting of disodium phenyl dibenzimidazole tetrasulfonate, hexyl 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoate (INCI diethylamino hydroxybenzoyl hexyl benzoate), methoxypropylamino cyclohexenylidene ethoxyethylcyanoacetate (MCE), 1-(4-(1,1-dimethylethyl)phenyl)-3-(4-methoxyphenyl)propane-1,3-dione (INCI butyl methoxydibenzoylmethane), terephthalylidene dicamphor sulfonic acid, and combinations thereof; and / or(2) at least one UVB filter, preferably selected from the group consisting of 4,4’,4”-(1,3,5-triazine-2,4,6-triyltriimino)tris-benzoic acid-tris(2-ethylhexyl)ester (INCI ethylhexyl triazone), 4,4’-[[6-[[4-[[(1,1-dimethylethyl)amino]carbonyl]phenyl]amino]-1,3,5-triazin-2,4-diyl]diimino]bis-benzoic acid-bis(2-ethylhexyl)ester (INCI diethylhexyl butamido triazone), phenylbenzimidazole sulfonic acid,, and combinations thereof; and / or(3) at least one broadband UV filter, preferably selected from the group consisting of bisethylhexyloxyphenol methoxyphenyl triazine (INCI bis-ethylhexyloxyphenol methoxyphenyl triazine), 2-(2H-benzotriazol-2-yl)-6-[(2-ethylhexyloxy)methyl]-4-methylphenol, 2-(2H-benzotriazol-2-yl)-4-methyl-6-[2-methyl-3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]-1-disiloxanyl]propyl]phenol (INCI drometrizole trisiloxane), 2,2'-methylenbis[6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol] (INCI methylene Bis-benzotriazolyl tetramethylbutylphenol), phenylene bis-diphenyltriazine (PBDT), and combinations thereof; and / or(4) at least one organic particulate UV filter is selected from the group consisting of 2,2'-methylene bis[6- (2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol] (INCI methylene bis-benzotriazolyl tetramethylbutylphenol), 2,4,6-tris(biphenyl-4-yl)-1,3,5-triazine (INCI tris-biphenyl triazine), 1,1 ’-(1,4-pipe razined iy I) bis[1 -[2-[4-(diethylamino)-2-hydroxybenzoyl]phenyl]-methanone (INCI bis- (diethylaminohydroxybenzoyl benzoyl) piperazine), 5,6,5’,6’-tetraphenyl-3-3’-(1,4-phenylene)bis(1,2,4-triazine) (INCI phenylene bis-diphenyltriazine, PBDT), micronized 1,4-di(benzoxazole-2'-yl)benzene and combinations thereof; and / or(5) at least one inorganic UV filter, preferably selected from the group consisting of titanium dioxide, zinc oxide, iron oxide, cerium oxide and mixtures thereof; and / or(6) at least one organic UV filter, preferably selected from the group consisting of ethylhexyl methoxycinnamate, ethylhexyl salicylate, homosalate, amiloxate, padimate O, shinorine, gadusol, mycosporine-2 glycine, porphyra-334, or cyanoacrylates, the cyanoacrylates optionally being selected(7) at least one organic UV filter, preferably selected from the group consisting of croconic acid derivatives, N-[(3E)-3-[(4-Methoxyphenyl)imino]-5,5-dimethyl-1-cyclohexen-1-yl]glycine, caprylyloxyphenylamino dimethyltetrahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylhexahydro benzothiazine carboxylic acid, Ethyl (3R)-3,4,5,6,7,8-hexahydro-8-[(4-methoxyphenyl)imino]-6,6-dimethyl-2H-1,4-benzothiazine-3-carboxylate, methoxyphenylimino dimethylcyclohexenyl ethyl glycinate, feruloyl hemp glycerides, feruloyl glycerides, feruloyl soybean glyceride FSG-33, feruloyl coconut glyceride FCG-33, feruloyl hemp glyceride FHG-33, ferulic acid, caffeic acid phenethyl ester, quercetin, methylsalicylate, vanillic acid, menthyl anthranilate, rutin, hispolon, Bis(cyano butylacetate) anthracenediylidene, trolamine salicylate, resveratrol trimethyl ether, ethyl ferulate, chlorogenic acid, methyl vanillate, ethyl protocatechuate, genistein, ellagic acid, pongamol, daidzein, luteolin, acetovanillone, caffeic acid, kaempferol, apigenin, sinapic acid, folic acid, troxerutin, p-coumaric acid, melanin, 3,4,5-trimethoxycinnamic acid, Kaempferia galanga root extract, ethylhexyl methoxycrylene, protocatechu ic acid, lignin, lignosulfonate, coffee bean extract, mycosporine-like amino acids, gadusosporines, hipposudoric acid, norhipposudoric acid, 2-Methylphenyl (2E)-3-(4-methoxyphenyl)-2-propenoate, 2-Propenoic acid, 3-(4-methoxyphenyl)-, 2-methylphenyl ester.

8. Composition comprising(1) at least one compound of formula (I)or a salt, hydrate, tautomer or stereoisomer thereof;whereinR1is H or methyl;R2, R3, R4and R5are independently selected from H, C1-C10alkyl, and -O(C1-C10alkyl) or R4and R5combine to form together with the carbon atoms to which they are attached a phenyl ring;R6is H or -O-R9;R7and R8are selected from H, -Ar or C1-C10 alk(en)ylene-Ar, wherein Ar is an optionally substituted aryl or heteroaryl group, wherein at least one of R7and R8is not H; orR5and one of R7and R8combine to form an -O- group;R9is optionally substituted 5- or 6-membered heterocyclyl;wherein if an aryl or heteroaryl group is substituted, it is substituted by 1 to 3 substituent(s) selected from C1-C10 alkyl, -OH, -O(Ci-C4 alkyl), -C(=O)-O(C1-C4alkyl), -N(C1-C4alkyl)2, aryl, and C1-C10alk(en)ylene-aryl, or two (vicinal) substituents combine to form a cyclic group of the formula -O-(CH2)n-O- with n being 1 or 2; andwherein if a heterocyclyl group is substituted, it is substituted by one or more substituents selected from -OH, C1-C4 alkyl and (C1-C4 alkylene)-OR10, wherein R10is 5- or 6-membered heterocyclyl optionally substituted by one or more substituents selected from -OH and methyl;and(2) at least one further UV filter different to the compounds of formula (I), preferably selected from(i) at least one UVA filter, preferably selected from the group consisting of disodium phenyl dibenzimidazole tetrasulfonate, hexyl 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoate (INCI diethylamino hydroxybenzoyl hexyl benzoate), methoxypropylamino cyclohexenylidene ethoxyethylcyanoacetate (MCE), 1-(4-(1,1-dimethylethyl)phenyl)-3-(4-methoxyphenyl)propane-1,3-dione (INCI butyl methoxydibenzoylmethane), terephthalylidene dicamphor sulfonic acid, and combinations thereof; and / or(ii) at least one UVB filter, preferably selected from the group consisting of 4,4’,4”-(1,3,5-triazine-2,4,6-triyltriimino)tris-benzoic acid-tris(2-ethylhexyl)ester (INCI ethylhexyl triazone), 4,4’-[[6-[[4-[[(1,1-dimethylethyl)amino]carbonyl]phenyl]amino]-1,3,5-triazin-2,4-diyl]diimino]bis-benzoic acid-bis(2-ethylhexyl)ester (INCI diethylhexyl butamido triazone), phenylbenzimidazole sulfonic acid,, and combinations thereof; and / or(iii) at least one broadband UV filter, preferably selected from the group consisting of bisethylhexyloxyphenol methoxyphenyl triazine (INCI bis-ethylhexyloxyphenol methoxyphenyl triazine), 2-(2H-benzotriazol-2-yl)-6-[(2-ethylhexyloxy)methyl]-4-methylphenol, 2-(2H-benzotriazol-2-yl)-4-methyl-6-[2-methyl-3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]-1-disiloxanyl]propyl]phenol (INCI drometrizoletrisiloxane), 2,2'-methylenbis[6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol] (INCI methylene Bis-benzotriazolyl tetramethylbutylphenol), phenylene bis-diphenyltriazine (PBDT), and combinations thereof; and / or(iv) at least one organic particulate UV filter is selected from the group consisting of 2,2'-methylene bis[6- (2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol] (INCI methylene bis-benzotriazolyl tetramethylbutylphenol), 2,4,6-tris(biphenyl-4-yl)-1,3,5-triazine (INCI tris-biphenyl triazine), 1,1 ’-(1,4-pipe razined iy I) bis[1 -[2-[4-(diethylamino)-2-hydroxybenzoyl]phenyl]-methanone (INCI bis- (diethylaminohydroxybenzoyl benzoyl) piperazine), 5,6,5’,6’-tetraphenyl-3-3’-(1,4-phenylene)bis(1,2,4-triazine) (INCI phenylene bis-diphenyltriazine, PBDT), micronized 1,4-di(benzoxazole-2'-yl)benzene and combinations thereof; and / or(v) at least one inorganic UV filter, preferably selected from the group consisting of titanium dioxide, zinc oxide, iron oxide, cerium oxide and mixtures thereof; and / or(vi) at least one organic UV filter, preferably selected from the group consisting of ethylhexyl methoxycinnamate, ethylhexyl salicylate, homosalate, amiloxate, padimate O, shinorine, gadusol, mycosporine-2 glycine, porphyra-334, or cyanoacrylates, the cyanoacrylates optionally being selected(vii) at least one organic UV filter, preferably selected from the group consisting of croconic acid derivatives, N-[(3E)-3-[(4-Methoxyphenyl)imino]-5,5-dimethyl-1-cyclohexen-1-yl]glycine, caprylyloxyphenylamino dimethyltetrahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylhexahydro benzothiazine carboxylic acid, Ethyl (3R)-3,4,5,6,7,8-hexahydro-8-[(4-methoxyphenyl)imino]-6,6-dimethyl-2H-1,4-benzothiazine-3-carboxylate, methoxyphenylimino dimethylcyclohexenyl ethyl glycinate, feruloyl hemp glycerides, feruloyl glycerides, feruloyl soybean glyceride FSG-33, feruloyl coconut glyceride FCG-33, feruloyl hemp glyceride FHG-33, ferulic acid, caffeic acid phenethyl ester, quercetin, methylsalicylate, vanillic acid, menthyl anthranilate, rutin, hispolon, Bis(cyano butylacetate) anthracenediylidene, trolamine salicylate, resveratrol trimethyl ether, ethyl ferulate, chlorogenic acid, methyl vanillate, ethyl protocatechuate, genistein, ellagic acid, pongamol, daidzein, luteolin, acetovanillone, caffeic acid, kaempferol, apigenin, sinapic acid, folic acid, troxerutin, p-coumaric acid, melanin, 3,4,5-trimethoxycinnamic acid, Kaempferia galanga root extract, ethylhexyl methoxycrylene, protocatechu ic acid, lignin, lignosulfonate, coffee bean extract, mycosporine-like amino acids, gadusosporines, hipposudoric acid, norhipposudoric acid, 2-Methylphenyl (2E)-3-(4-methoxyphenyl)-2-propenoate, 2-Propenoic acid, 3-(4-methoxyphenyl)-, 2-methylphenyl ester; and, optionally,(3) at least one other component selected from the group consisting of: emulsifiers, emollients, thickeners, cosmetic oils, sensory enhancers, consistency agents, film forming agents, UV performance boosters, preservatives, and perfumes.

9. The composition according to claim 8, wherein in the compound of formula (I)(1) R1is H or methyl, preferably H;(2) R2is H;(3) R3is H, methyl, hydroxy, -O(2-ethylhexyl), -O(methyl), or -O(isopropyl);(4) R4is H or methyl or combines with R5to form together with the carbon atoms to which they are attached a phenyl ring;(5) R5is H or methoxy, or combines with R4to form together with the carbon atoms to which they are attached a phenyl ring, or combines with R7to form an -O- group;(6) R6is H or O-heterocyclyl of formula (III)(group; and / or(8) R8is optionally substituted aryl or heteroaryl, preferably, optionally substituted pyrrole, optionally substituted furan, optionally substituted benzofuran, optionally substituted indole, and phenyl of formula (II)wherein R11, R13and R15are independently selected from H, C3-C10 alkyl, and -O(C3-C10alkyl); and R12and R14are independently selected from H, C3-C10 alkyl, -O(C3-C10alkyl), and -N(C1-C4alkyl).

10. The composition according to claim 9, wherein R8is selected from the group consisting of 3-pyrrolyl, N-methyl-3-pyrrolyl, 3-furanyl, 5-methyl-3-furanyl, 2-benzofuranyl, 3-indolyl, N-methyl-3-indolyl, 5-methoxyindolyl, 4-methoxyphenyl, 4-isopropylphenyl, 4-(2-ethylhexoxy)phenyl, 2-(2-ethylhexoxy)phenyl, phenyl, 4-isopropoxyphenyl, 1,3-benzodioxol-5-yl, 2,4-dimethoxyphenyl, 2-methoxyphenyl, 4-(diethylamino)phenyl, 2,4-dihydroxyphenyl, 2,3-dipropoxyphenyl, 2,4-di-n-hexoxyphenyl, 2-n-octoxyphenyl, 2-hydroxyphenyl, 4-((E)-ethen-2-yl salicylate)phenyl, 3-(diethylamino)phenyl, 4-n-hexoxyphenyl, 4-biphenyl, 4-naphthyl, 4-carboxyethylphenyl, and (E)-ethen-2-yl phenyl.

11. The composition according to any one of claims 6 to 10, wherein the compound of formula (I) is selected from the following compoundsor a salt, hydrate, tautomer or stereoisomer thereof.

12. The composition according to any one of claims 6 to 11, wherein the compound is any one of:or a salt, hydrate, tautomer or stereoisomer thereof.

13. The composition according to any one of claims 6 to 12, further comprising one or more further compounds selected from the group consisting of C12-C15alkyl benzoates, coco glycerides, coconut oil, dibutyl adipate, dodecyl lactate, ethylhexyl benzoate, glycerol, glyceryl stearate, lauryl glycoside, lauryl lactate,(medium chain) triglycerides, phenoxyethanol, phenoxy ethyl caprylate, polyglyceryl-2-dipolyhydroxy-stearate, stearoyl glutamate and salts thereof, stearyl alcohol, dicarboxymethyl alaninate and salts thereof, xanthan gum, and ethanol.

14. The composition according to any one of claims 6 to 13, wherein(1) the composition is a pharmaceutical, home care or personal care composition, preferably a sunscreen or daily care composition; and / or(2) said compound of formula (I) preferably has a biodegradability of at least 20% degradation as determined over 28 days at 22°C according to OECD 301F; and / or(3) the organic components of the composition have a biodegradability of at least 20% degradation as determined over 28 days at 22°C according to OECD 301F; and / or(4) the composition is a personal care composition and has an SPF of at least 15.

15. The compound according to any one of claims 1 to 4 or the composition according to any one of claims 6 to 14 for use to protect skin against UV radiation.

16. Use of a compound of formula (I) any one of claims 1 to 5 as an organic UV filter or as a light stabilizer to protect ingredients against photolytic degradation in a pharmaceutical, personal care or home care composition.

17. The use according to claim 16, wherein said UV filter of formula (I) optionally has a biodegradability of at least 20% as determined over 28 days at 22°C according to OECD 301F.

18. The composition of any one of claims 6 to 14 or the use according to claim 16 or 17, wherein the compound of formula (I) is comprised in said composition in an amount relative to the total weight of the composition of 0.5 to 50 wt.-%, preferably from 1 to 45 wt.-%, more preferably from 2 to 40 wt.-%, and in particular from 2.5 to 35 wt.-%.

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