Cumestane-like antioxidants and UV absorbers

2008 
A stabilized composition comprising (a) an organic material subjected to degradation by exposure to UV radiation and / or the deleterious effects of radicals, which is selected from natural or synthetic organic polymers, cosmetic formulations, pharmaceutical formulations, products foodstuffs, and (b) an effective stabilizing amount of a compound of the general formula (I) wherein X is O, NH or NR15; R1, R2, R3 and R4 are independently of each other H, halogen, hydroxy, C1-C24 alkyl, C1-C24 alkyl which is substituted by at least one E and / or interrupted by at least one D, perfluoroalkyl C1-C24 , C6-C14 perfluoroaryl, C5-C12 cycloalkyl; C5-C12 cycloalkyl which is substituted by G and / or is interrupted by -S-, -O-, or -NR15-; -NR15R16; C1-C24 thioalkyl; -PR17R18; C5-C12 cycloalkoxy; C5-C12 cycloalkoxy which is substituted by G; C6-C24 aryl; C6-C24 aryl which is substituted by G, C1-C24 alkyl, C5-C12 cycloalkyl, C7-C25 aralkyl, C6-C14 perfluoroaryl, or C1-C24 haloalkyl such as C1-C24 perfluoroalkyl; C2-C20 heteroaryl; C2-C20 heteroaryl which is substituted by G, C1-C24 alkyl, C5-C12 cycloalkyl, C7-C25 aralkyl, C6-C14 perfluoroaryl, or C1-C24 haloalkyl such as C1-C24 perfluoroalkyl; C2-C24 alkenyl; C2-C24 alkynyl; C1-C24 alkoxy; C1-C24 alkoxy which is substituted by at least one E and / or is interrupted by at least one D; C7-C25 aralkyl; C7-C25 aralkyl, which is substituted by G; C7-C25 aralkoxy, C7-C25 aralkoxy which is substituted by G; or -OCO-R19 or -CO-R19, or R1 and R2 together are a group where R5, R6, R7, R8, R9, R10, R11, R12, R13 and R14 are independently of each other H, halogen, hydroxy , C1-C24 alkyl, C1-C24 alkyl which is substituted by at least one E and / or is interrupted by at least one D, perfluoroalkyl C1-C24, perfluoroaryl C6-C14, especially pentafluorophenyl, cycloalkyl C5-C12, cycloalkyl C5- C12 which is substituted by at least one G and / or is interrupted by at least one S-, -O-, or -NR15-, C5-C12 cycloalkoxy, C5-C12 cycloalkoxy which is substituted by G, C6-C24 aryl, C6-C24 aryl which is substituted by at least one G, C2-C20 heteroaryl, C2-C20 heteroaryl which is substituted by at least one G, C2-C24 alkenyl, C2-C24 alkynyl, C1-C24 alkoxy, C1-C24 alkoxy which is substituted by at least one E and / or is interrupted by at least one D, C7-C25 aralkyl, C7-C25 aralkyl, which is substituted by at least one G, C7-C25 aralkoxy, C7-C25 aralkoxy which is substituted by at least one G, or are -CO-R19, D is -CO-; -COO-; -S-; -SW-; -SO2-; -OR-; -NR15-; -POR17-; -CR20 = CR21-; or -C: C-; E is -OR22; -SR22; -NR15R16; - [NR15R16R24] + Z-; -COR19; -COOR23; -CONR15R16; -CN; -N3; -OCOOR23; or halogen; and G is E, or C1-C24 alkyl, wherein R20, R21, R15, R16 and R24 are independently of each other H; C6-C18 aryl; C6-C18 aryl which is substituted by a C1-C24 alkyl and / or C1-C24 alkoxy; C1-C24 alkyl; or C1-C24 alkyl which is interrupted by at least one -O-; or R15 and R16 together form a five or six member ring, in particular Z is an equivalent of an anion, especially a cosmetically acceptable anion such as halogen, preferably Cl; R19 is H; C6-C18 aryl; C6-C18 aryl which is substituted by a C1-C24 alkyl, hydroxy and / or C1-C24 alkoxy; C6-C18 aryloxy; C6-C18 aryloxy which is substituted by a C1-C24 alkyl, hydroxy and / or C1-C24 alkoxy; C1-C24 alkyl; or C1-C24 alkyl which is interrupted by at least one -O-; C1-C24 alkoxy; or C1-C24 alkoxy which is interrupted by at least one -O-; R22 and R23 are independently of each other H; C6-C18 aryl; C6-C18 aryl, which is substituted by a C1-C24 alkyl or C1-C24 alkoxy; C1-C24 alkyl; or C1-C24 alkyl which is interrupted by at least one -O-; and R17 and R18 are independently of each other C1-C24 alkyl, C6-C18 aryl, or C6-C18 aryl, which is substituted by a C1-C24 alkyl; R3 and / or R4 can also be a mono-, di- or oligosaccharide alpha- or beta-linked residue to the phenolic ring system either directly or via phenolic oxygen.
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