S-triazine sunscreens bearing hindered para-aminobenzalmalonate/para-aminobenzalmalonamide and aminobenzoate/aminobenzamide substituents

Abstract

Novel s-triazine sunscreens have the structural formula (I): and are formulated into cosmetic/dermatological photoprotective compositions useful for photoprotecting keratinous substances against the damaging effects of UV-radiation.

1 . An s-triazine compound having the following structural formula (I): 
       
         
           
           
               
               
           
         
         in which: 
         the radicals X, which may be identical or different, are each —O— or —NR 6 —; 
         the radicals R a , which may be identical or different, are each a radical of formula (II): 
       
       
         
           
           
               
               
           
         
         in which: 
         the radicals R 1  and R 2 , which may be identical or different, are each a linear or branched C 1 -C 8  alkyl radical, with the proviso that R 1  and R 2  can together form a C 5 -C 8  ring member, optionally substituted by 1, 2 or 3 linear or branched C 1 -C 4  alkyl radical(s), 
         the radicals R 3 , R 4  and R 5 , which may be identical or different, are each a hydrogen atom or a linear or branched C 1 -C 4  alkyl radical; 
         n has the value 0 or 1; 
         m has the value 0 or 1; 
         with the proviso that: 
         (i) when n=1 and R 4  is hydrogen, then m is equal to 0 and, 
         (ii) when R 1  and R 2  together form a C 5 -C 8  ring, then the sum n+m is other than 2; 
         the radical R 6  is hydrogen or a C 1 -C 8  alkyl radical; 
         the radical R b  is a linear or branched and optionally unsaturated C 1 -C 20  alkyl radical, a C 5 -C 12  cycloalkyl radical optionally substituted by 1 to 3 linear or branched C 1 -C 4  alkyl radicals, the —(CH 2 CHR 7 —O) q   8  radical or the —CH 2 —CH(OH)—CH 2 —O—R 8  radical; 
         the radical R 7  is hydrogen or methyl; 
         the radical R 8  is hydrogen or a C 1 -C 8  alkyl radical; 
         q=1-20; 
         the COXR b  group can be in the ortho, meta or para position with respect to the amino group; 
         the radical R b  is a saturated or unsaturated and linear or branched C 1 -C 20  alkyl radical, the OH radical or a linear or branched C 1 -C 20  alkoxy radical; and 
         2 is equal to 0, 1 or 2. 
       
     
     
         2 . The s-triazine compound as defined by  claim 1 , wherein formula (I):
 (a) n=m=0 and   (b) R 1 , R 2  and R 3  are each a C 1 -C 4  alkyl radical,   
       or R 3  is hydrogen and R 1  and R 2  together form a C 5 -C 8  ring member optionally substituted by one or two alkyl radicals. 
     
     
         3 . The s-triazine compound as defined by  claim 1 , wherein formula (I):
 (a) n=m=0 and   (b) R 1 , R 2  and R 3  are each methyl,   
       or R 3  is hydrogen and R 1  and R 2  together form a cyclohexyl ring. 
     
     
         4 . The s-triazine compound as defined by  claim 1 , wherein formula (I):
 (a) n=1 and R 4  is an alkyl, or m=1 and R 5  is an alkyl radical, and   (b) R 1  and R 2  are each a C 1 -C 4  alkyl radical.   
     
     
         5 . The s-triazine compound as defined by  claim 1 , wherein formula (I):
 (a) n=1 and R 4  is methyl or m=1 and R 5  is methyl, and   (b) R 1  and R 2  are each methyl.   
     
     
         6 . The s-triazine compound as defined by  claim 1 , selected from the group consisting of those of the following formulae (1) to (10): 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         7 . The s-triazine compound as defined by  claim 1 , the same being 2,4-bis(dineopentyl 4′-aminobenzalmalonate)-6-(butyl 4″-aminobenzoate)-s-triazine. 
     
     
         8 .- 18 . (canceled) 
     
     
         19 . A synthetic polymer or a glass comprising a photostabilizing amount of at least one s-triazine compound as defined by  claim 1 .