Naphthyltriazines as stabilizers for organic material

Abstract

Novel compounds of formula (I) are described, wherein E corresponds to the formula (a) or to the formula (b) and the radicals R 1 , R 2 , R 11 , R 22 , R′ 22 , R 33 , and R′ 33 are as defined in claim 1. Compounds of formula (I) are suitable for stabilising organic material, especially plastics materials, surface-coatings, cosmetic preparations, sun protection agents or photographic material, against damage by light, oxygen and/or heat.

1 . A compound of formula I  
       
         
           
           
               
               
           
         
       
       wherein 
 E corresponds to the formula  
                     
  or to the formula  
                     
 R 1  is hydrogen or OR 3 ;  
 R 2  is H, C 1 -C 18 alkyl; C 2 -C 6 alkenyl; phenyl; phenyl substituted by C 1 -C 8 alkyl or by C 1 -C 8 alkoxy; C 7 C 11 phenylalkyl; C 5 -C 12 cycloalkyl; COOR 4 ; CN; NH 2 , NHR 7 , —N(R 7 )(R 8 ), NH—CO—R 5 ; halogen; C 1 -C 18 haloalkyl; —S—R 3  or —O—R 3 ;  
 R 3  is H, C 1 -C 18 alkyl; C 5 -C 12 cycloalkyl; C 3 -C 18 alkenyl; phenyl; C 1 -C 18 alkyl that is substituted by phenyl, vinylphenyl, OH, C 1 -C 18 alkoxy, C 5 -C 12 cycloalkoxy, C 3 -C 18 alkenyloxy, halogen, —COOH, —COOR 4 , —O—CO—R 5 , —O—CO—O—R 6 , —CO—NH 2 , —CO—NHR 7 , —CO—N(R 7 )(R 8 ), CN, NH 2 , NHR 7 , —N(R 7 )(R 8 ), —NH—CO—R 5 , phenoxy, C 1 -C 18 alkyl-substituted phenoxy, phenyl-C 1 -C 4 -alkoxy, C 6 -C 15 bicycloalkoxy, C 6 -C 15 bicycloalkyl-alkoxy, C 6 -C 15 bicycloalkenyl-alkoxy and/or by C 8 -C 15 tricycloalkoxy; C 5 -C 12 cycloalkyl that is substituted by OH, C 1 -C 4 alkyl, C 2 -C 6 alkenyl or by —O—CO—R 5 ; —CO—R 9  or —SO 2 —R 10 ; or R 3  is C 3 -C 50 alkyl that is interrupted by one or more oxygen atoms and/or is substituted by OH, phenoxy or by C 7 -C 18 alkylphenoxy; or R 3  has one of the definitions —A; —CH 2 —CH(XA)—CH 2 —O—R 12 ; —CR 13 R′ 13 —(CH 2 ) m —X—A;  
 —CH 2 —CH(OA)—R 14 ; —CH 2 —CH(OH)—CH 2 —XA;  
                     
 —CR 15 R′ 15 —C(═CH 2 )—R″ 15 ; —CR 13 R′ 13 —(CH 2 ) m —CO—X—A;  
 —CR 13 R′ 13 —(CH 2 ) m —CO—O—CR 15 R′ 15 —C(═CH 2 )—R″ 15  or —CO—O—CR 15 R′ 15 —C(═CH 2 )—R″ 15 , wherein A is —CO—CR 16 ═CH—R 17 ;  
 R 4  is C 1 -C 18 alkyl; C 3 -C 18 alkenyl; phenyl; C 7 C 11 phenylalkyl; C 5 -C 12 cycloalkyl; or C 3 -C 50 alkyl that is interrupted by one or more of —O—, —NH—, —NR 7  and —S— and may be substituted by OH, phenoxy or by C 7 -C 18 alkylphenoxy; or is C 2 -C 12 hydroxyalkyl;  
 R 5  is H; C 1 -C 18 alkyl; C 1 -C 18 alkyl substituted by COOH or by COOR 4 ; C 2 -C 18 alkenyl; C 2 -C 18 -alkenyl substituted by COOH or by COOR 4 ; C 5 -C 12 cycloalkyl; phenyl; C 7 -C 11 phenylalkyl;  
 C 6 -C 15 bicycloalkyl; C 6 -C 15 bicycloalkenyl; or C 6 -C 15 tricycloalkyl;  
 R 6  is H; C 1 -C 18 alkyl; C 3 -C 18 alkenyl; phenyl; C 7 -C 11 phenylalkyl; or C 5 -C 12 cycloalkyl;  
 R 7  and R 8 , independently of each other, are C 1 -C 12 alkyl; C 3 -C 12 alkoxyalkyl; C 4 -C 16 dialkyl-aminoalkyl; or C 5 -C 12 cycloalkyl; or together form C 3 -C 9 -alkylene, -oxaalkylene or -azaalkylene;  
 R 9  is C 1 -C 18 alkyl; C 2 -C 18 alkenyl; phenyl; C 5 -C 12 cycloalkyl; C 7 -C 11 phenylalkyl; C 6 -C 15 -bicycloalkyl, C 6 -C 15 bicycloalkyl-alkyl, C 8 -C 15 bicycloalkenyl, or C 6 -C 15 tricycloalkyl;  
 R 10  is C 1 -C 12 alkyl; phenyl; naphthyl or C 7 -C 14 alkylphenyl;  
 the radicals R 11 , R 22  and R 33 , independently of one another, are H; C 1 -C 18 alkyl; C 3 -C 6 alkenyl;  
 C 5 -C 12 cycloalkyl; phenyl; naphthyl; biphenylyl; C 7 -C 11 phenylalkyl; C 7 -C 14 alkylphenyl; halogen;  
 C 1 -C 18 haloalkyl; or C 1 -C 18 alkoxy;  
 R 12  is C 1 -C 18 alkyl; C 3 -C 18 alkenyl; phenyl; phenyl substituted by from one to three of the radicals C 1 -C 8 alkyl, C 1 -C 8 alkoxy, C 3 -C 8 alkenyloxy, halogen and trifluoromethyl; C 7 -C 11 phenylalkyl; C 5 -C 12 cycloalkyl; C 6 -C 15 tricycloalkyl; C 6 -C 15 bicycloalkyl; C 6 -C 15 bicycloalkyl-alkyl; C 6 -C 15 bicycloalkenyl-alkyl; —CO—R 5 ; or C 3 -C 50 alkyl that is interrupted by one or more of —O—, —NH—, —NR 7 — and —S— and may be substituted by OH, phenoxy or by C 7 -C 18 alkylphenoxy;  
 R 13  and R′ 13 , independently of each other, are H; C 1 -C 18 alkyl; or phenyl;  
 R 14  is C 1 -C 18 alkyl; C 3 -C 12 alkoxyalkyl; phenyl; or phenyl-C 1 -C 4 alkyl;  
 R 15 , R′ 15  and R″ 15 , independently of one another, are H or CH 3 ;  
 R 16  is H; —CH 2 —COO—R 4 ; C 1 -C 4 alkyl; or CN;  
 R 17  is H; —COOR 4 ; C 1 -C 17 alkyl; or phenyl;  
 R′ 22  and R′ 33 , independently of each other, have one of the definitions of R 11  or OR 3 ; or are NH 2 , NHR 7 , NH—CO—R 5 ; —S—R 3  or —N(R 7 )(R 8 );  
 X is —NH—; —NR 7 —; —O—; —NH—(CH 2 ) p —NH—; or —O—(CH 2 ) q —NH—;  
 and the indices are as follows:  
 m is the number 0-19;  
 n is the number 1-8;  
 p is the number 0-4; and  
 q is the number 2-4.  
 
     
     
         2 . A compound of formula I according to  claim 1 , wherein 
 R 1  is hydrogen or OR 3 ;    R 2  is H, C 1 -C 18 alkyl; C 2 -C 6 alkenyl; phenyl; phenyl substituted by C 1 -C 8 alkyl or by C 1 -C 8 alkoxy; NH—CO—R 5 ; halogen; C 1 -C 18 haloalkyl; or C 1 -C 18 alkoxy;    R 3  is H, C 1 -C 18 alkyl; C 5 -C 12 cycloalkyl; C 3 -C 18 alkenyl; phenyl; C 1 -C 18 alkyl that is substituted by phenyl, vinylphenyl, OH, C 1 -C 18 alkoxy, C 5 -C 12 cycloalkoxy, C 3 -C 18 alkenyloxy, halogen, —COOH, —COOR 4 , —O—CO—R 5 , —O—CO—O—R 6 , —CO—NH 2 , —CO—NHR 7 , —CO—N(R 7 )(R 8 ), CN, NH 2 , NHR 7 , —N(R 7 )(R 8 ), —NH—CO—R 5 , phenoxy, C 1 -C 18 alkyl-substituted phenoxy and/or by phenyl-C 1 -C 4 alkoxy; C 5 -C 12 cycloalkyl that is substituted by OH, C 1 -C 4 alkyl, C 2 -C 6 alkenyl or by —O—CO—R 5 ; or R 3  is —SO 2 —R 10 ; or R 3  is C 3 -C 50 alkyl that is interrupted by one or more oxygen atoms and/or is substituted by OH, phenoxy or by C 7 -C 18 alkylphenoxy; or R 3  has one of the definitions —CO—CH═CH 2  and —CO—C(CH 3 )═CH 2 ;    R 4  is C 1 -C 18 alkyl; C 3 -C 18 alkenyl; phenyl; C 7 -C 11 phenylalkyl; C 5 -C 12 cycloalkyl; or C 3 -C 50 alkyl that is interrupted by one or more of —O—, —NH—, —NR 7 — and —S— and may be substituted by OH, phenoxy or by C 7 -C 18 alkylphenoxy; or is C 2 -C 12 hydroxyalkyl;    R 5  is H; C 1 -C 18 alkyl; C 2 -C 18 alkenyl; C 5 -C 12 cycloalkyl; phenyl; or C 7 C 11 phenylalkyl;    R 6  is H; C 1 -C 18 alkyl; C 3 -C 18 alkenyl; phenyl; C 7 -C 11 phenylalkyl; or C 5 -C 12 cycloalkyl;    R 7  and R 8 , independently of each other, are C 1 -C 12 alkyl; C 3 -C 12 alkoxyalkyl; C 4 -C 16 dialkyl-aminoalkyl; or cyclohexyl; or together form C 3 -C 9 -alkylene or -oxaalkylene;    R 10  is C 1 -C 12 alkyl; phenyl; naphthyl or C 7 -C 14 alkylphenyl;    the radicals R 11 , R 22  and R 33 , independently of one another, are H, C 7 -C 11 phenylalkyl or C 1 -C 8 alkyl; and    R′ 22  and R′ 33 , independently of each other, are H; C 1 -C 8 alkyl; C 3 -C 6 alkenyl; C 7 -C 11 phenylalkyl; C 5 -C 12 cycloalkyl; phenyl; naphthyl; biphenylyl; C 7 -C 11 phenylalkyl; C 7 -C 14 alkylphenyl; NHR 7 ; —N(R 7 )(R 8 ); halogen or C 1 -C 18 haloalkyl; or have one of the definitions of OR 3 .    
     
     
         3 . A compound according to  claim 1  corresponding to formula IIa or IIb  
       
         
           
           
               
               
           
         
       
       wherein 
 E corresponds to the formula  
                     
 E′ corresponds to the formula  
                     
 G corresponds to the formula  
                     
 and G′ corresponds to the formula  
                     
 
     
     
         4 . A compound of formula I according to  claim 1 , wherein 
 R 1  is hydrogen or OR 3 ;    R 2  is H, C 1 -C 8 alkyl; phenyl; phenyl substituted by methyl or by methoxy; NH—CO—R 5 ; trifluoromethyl; or C 1 -C 18 alkoxy;    R 3  is H, C 1 -C 18 alkyl; cyclohexyl; C 3 -C 18 alkenyl; C 1 -C 18 alkyl that is substituted by phenyl, OH, C 1 -C 18 alkoxy, cyclohexyloxy, halogen, —COOH, —COOR 4 , —O—CO—R 5 , —CO—NHR 7 , —CO—N(R 7 )(R 8 ), CN, NHR 7 , —N(R 7 )(R 8 ), —NH—CO—R 5  and/or by phenyl-C 1 -C 4 alkoxy; or cyclohexyl that is substituted by OH, C 1 -C 4 alkyl, C 2 -C 6 alkenyl or by —O—CO—R 5 ;    R 4  is C 1 -C 18 alkyl; C 7 -C 11 phenylalkyl; C 5 -C 12 cycloalkyl; or C 2 -C 12 hydroxyalkyl;    R 5  is H; C 1 -C 18 alkyl; C 2 -C 8 alkenyl; cyclohexyl; phenyl; or C 7 -C 11 phenylalkyl;    R 7  and R 8 , independently of each other, are C 3 -C 12 alkyl or cyclohexyl; or together form C 3 -C 9 oxaalkylene;    the radicals R 11 , R 22  and R 33 , independently of one another, are H, C 7 -C 11 phenylalkyl or C 1 -C 8 alkyl; and    R′ 22  and R′ 33 , independently of each other, are H; C 1 -C 8 alkyl; C 3 -C 6 alkenyl; C 7 -C 11 phenylalkyl; C 5 -C 12 cycloalkyl; trifluoromethyl; phenyl; naphthyl; biphenylyl; C 7 -C 11 phenylalkyl; C 7 -C 14 alkylphenyl; or NHR 7  or —N(R 7 )(R 8 ); or have one of the definitions of OR 3 .    
     
     
         5 . A compound of formula IIa or IIb according to  claim 3 , wherein 
 E in formula IIa corresponds to one of the formulae                          E′ in formula IIb corresponds to the formula                          G corresponds to the formula                          and G′ corresponds to the formula                           and    R 1  is hydrogen or OR 3 ;    R 2  is H, C 1 -C 8 alkyl; methoxy or phenyl;    R 3  is H, C 1 -C 18 alkyl; C 1 -C 12 alkyl that is substituted by OH, C 1 -C 18 alkoxy, COOR 4  or by —O—CO—   R 5 ;    R 4  is C 1 -C 18 alkyl;    R 5  is H; C 1 -C 18 alkyl; or C 7 -C 11 phenylalkyl; and    R 22  is H or methyl; and    R′ 22  is H or C 1 -C 4 alkyl or has one of the definitions of OR 3 .    
     
     
         6 . A composition comprising A) an organic material that is sensitive to damage by light, oxygen and/or heat and B) as stabiliser at least one compound of formula I according to  claim 1 .  
     
     
         7 . A composition according to  claim 6  comprising components A) and B), wherein component A) is a synthetic organic polymer, a binder for surface-coatings, a recording material or animal or human hair.  
     
     
         8 . A composition according to  claim 6  comprising, in addition to components A) and B), as further component one or more compounds selected from pigments, dyes, plasticisers, antioxidants, flow improvers, further UV absorbers, metal passivators, metal oxides, organophosphorus compounds, hydroxylamines, sterically hindered amines, flame-proofing agents.  
     
     
         9 . A composition according to  claim 6  comprising from 0.01 to 10% by weight of component B) based on the weight of the composition.  
     
     
         10 . A composition according to  claim 6 , wherein component A) is a binder for surface-coatings or is a colour photographic material comprising, on a support, at least one photo-sensitive silver halide emulsion layer and optionally an intermediate layer and/or a protection layer, at least one of the said layers comprising component B).  
     
     
         11 . A recording material according to  claim 7  comprising component B) in an amount of from 0.001 to 10 g per m 2 .  
     
     
         12 . A method of stabilising organic material against damage by light, oxygen and/or heat, wherein a compound of formula I according to  claim 1  is mixed with or applied to that material.  
     
     
         13 . The use of a compound of formula I according to  claim 1  for stabilising organic material against damage by light, oxygen and/or heat.  
     
     
         14 . A cosmetic preparation comprising at least one or more compounds of formula I according to  claim 1  and at least one hair- and skin-cosmetically tolerable carrier or excipient.  
     
     
         15 . 2,4-Bis(4-methyl-1-naphthyl)-6-chloro-1,3,5-triazine; 
 2,4-bis(4-methoxy-1-naphthyl)-6-chloro-1,3,5-triazine;    2-(4-methoxy-1-naphthyl)-4-(4-hydroxy-1-naphthyl)-6-chloro-1,3,5-triazine;    2,4-bis(2-hydroxy-1-naphthyl)-6-chloro-1,3,5-triazine;    2,4-bis(2-methoxy-1-naphthyl)-6-chloro-1,3,5-triazine;    2-(2-methoxy-1-naphthyl)-4-(2-hydroxy-1-naphthyl)-6-chloro-1,3,5-triazine;    2,4-dichloro-6-(2-methoxy-1-naphthyl)-1,3,5-triazine.