Use of benzotropolone derivatives as uv absorbers and antioxidants and their use in sunscreens and/or cosmetic compositions

Abstract

Described is the use of benzotropolone and their derivatives, especially the compounds of formula (1); wherein R, R, R, Rand Rindependently of one another are hydrogen; OH; C-Calkyl, C-Cal-kenyl, C-Calkoxy, C-Ccycloalkyl or CChydroxyalkyl, which may be substituted by one or more E and/or interrupted by one or more D; C-Caryl, which may be substituted by one or more G; C-Cheteroaryl, which may be substituted by one or more G, C-Calkenyl, C-Calkynyl, C-Caralkyl, CN, or —CO—R; C-Cmono- or dialkylamino; COR; COOR; CONRR; CN; SOR; OCOOR; OCOR; NHCOOR; NRCOR; NH; *—(CO)—NH—(CH)—(PO)—(OR); —(CO)—O—(CH)—(PO)—(OR); sulphate; sulphonate; phosphate; phosphonate; —(CH)—[O—(SO)]—OR; —O—(CH)(CO)—R; —(O)—(CH)—(PO)—(OR); —(O)—(CH)—SO—OR; halogen; organosilanyl; organo-siloxanyl; or a sugar residue linked directly in an α- or β-mode via the anomeric oxygen to the benzotropolone system or via a linear or branched alkylene, alkenylene, alkadiene or alkatriene spacer (sugar-(CH)—(X)-benzotropolone system, wherein n=1-10 and X═—O—; —(CO)—; —O—CO—; —COO—, —NH—; —S—; —SO—); R, Rand Rindependently of one another are hydrogen; CCalkyl or C-C-cycloalkyl, which may be substituted by one or more E and/or interrupted by one or more D; C-Caryl, which may be substituted by one or more G; C-Cheteroaryl, which may be substituted by one or more G, C-Calkenyl, C-Calkynyl, C-Caralkyl, or COOR; COR; CONRR; SOR; SOR; PO(R); PO(R); organosilanyl; organosiloxanyl; or a sugar residue linked directly in an α- or β-mode via the anomeric oxygen to the benzotropolone system or via a linear or branched alkylene, alkenylene, alkadiene or alkatriene spacer (sugar-(CH)—(X)—*, wherein n=1-10 and X═—C(═O)—; —O—CO—*); Rand Rindependently from each other are hydrogen; CCalkyl or C-C-cycloalkyl which may be substituted by one or more E and/or interrupted by one or more D; C-Caryl, which may be substituted by one or more G; C-Cheteroaryl, which may be substituted by one or more G; organosilanyl; organosiloxanyl; or a sugar residue linked directly in an α- or β-mode via the anomeric oxygen or via a linear or branched alkylene, alkenylene, alkadiene or alkatriene spacer (sugar-(CH)—*, wherein n=1-10); or Rand Rtogether form a five or six membered ring, Ris hydrogen; or C-Calkyl; n, n, nand nindependently from each other are a number from 1 to 5; n, nand nindependently from each other are a 0; or 1; D is —CO—; —COO—; —S—; —SO—; —SO2-; —O—; —NR—; —SRR—; —POR—; —CR═CR—; or —C≡C—; and E is —OR; —SR; —NRR; —NRCOR; —COR; —COOR; —CONRR; —CN; halogen; Or SOR; SOR; PO(R); PO(R); organosilanyl; organosiloxanyl; or a sugar residue linked directly in an α- or β-mode via the anomeric oxygen or via a linear or branched alkylene, alkenylene, alkadiene or alkatriene spacer (sugar-(CH)n-(X)—*, wherein n=1-10 and X1=—O—; —C(═O)—; —O—CO—; —COO—; —NH—; —S—; —SO—); G is E; C-Calkyl, which is optionally interrupted by D; C-Cperfluoroalkyl; C-Calkoxy, which is optionally substituted by E and/or interrupted by D; wherein R, R, Rand Rindependently of each other are hydrogen; C-Caryl which is optionally substituted by OH, C-Calkyl or C-Calkoxy; C-Calkyl, which is optionally interrupted by —O—; or Ri4 and Ri5 together form a five or six membered ring, Ri6 is hydrogen; C6-Ci8aryl which is optionally substituted by OH, C-Calkyl or d-Calkoxy; C-Calkyl which is optionally interrupted by —O—; Ris H; C-Caryl which is optionally substituted by OH, C-Calkyl or C-Calkoxy; or d-Calkyl which is optionally interrupted by —O—; Ris hydrogen; C-Caryl, which is optionally substituted by OH, C-Calkyl or d-Calkoxy; C-Calkyl, which is optionally interrupted by —O—; Rand Rindependently of each other are hydrogen; C-Calkyl; C-Caryl which is optionally substituted by C-Calkyl; and Ris C-Calkyl; or C-Caryl, which is substituted by C-Calkyl; * means, that this radical is directed to the benzotropolone moiety; for the protection of human and animal hair and skin against UV radiation.