Stabilized organic material

Abstract

o-Hydroxyphenyl-s-triazines of the formula I in which n is 1 to 4 and R 1 to R 7 are as defined in claim 1, can be used, in combination with sterically hindered amines of the polyalkylpiperidine type, for stabilizing organic polymers. Some of these compounds are novel and can also be used without polyalkylpiperidine.

What is claimed is:  
     
         1 . An organic material which has been stabilized against damage caused by light, heat and oxygen and which contains 
 (a) at least one sterically hindered amine of the polyalkylpiperidine type and    (b) at least one o-hydroxyphenyl-s-triazine, wherein the triazine compound (b) is a compound of the formula I                          in which n is 1 to 4,    R 1  and R 2  independently of one another are H, OH, C 1 -C 12 alkyl, cyclohexyl or trifluoromethyl,    R 3  and R 4  independently of one another are H, OH, C 1 -C 12 alkyl, cyclohexyl, C 1 -C 18 alkoxy or halogen and, in the event that n=1, can also be a radical —OR 7 ,    R 5  and R 6  independently of one another are H. C 1 -C 12 alkyl or halogen,    R 7 , if n is 1, is a) C 1 -C 18 alkyl which is substituted by one or more of the groups OH, C 1 -C 18 alkoxy, C 3 -C 18 alkenoxy, halogen, phenoxy (which is unsubstituted or substituted by C 1 -C 18 alkyl, C 1 -C 18 alkoxy or halogen), furyloxy,                           —COOH, —COOR 9 , —CONH 2 , —CONHR 9 , —CON(R 9 )(R 10 ), —NH 2 , —NH 9 , —N(R 9 )(R 10 ), —NHCOR 11 , —CN and/or by —O—CO—R 11 ,    b) C 4 -C 50 alkyl which is interrupted by one or more O and can be substituted by OH or/and glycidyloxy,    c) C 3 -C 6 alkenyl,    d) glycidyl or a group                          e) cyclohexyl which is unsubstituted or substituted by OH or —OCOR 1 ,    f) C 7 -C 11 phenylalkyl which is unsubstituted or substituted by OH, Cl or CH 3 ,    g) —CO—R 12  or    h) —SO 2 —R 13 ,    and if n is 2, R 7  is a) C 2 -C 16 alkylene,    b) C 4 -C 12 alkenylene,    c) xylylene,    d) C 3 -C 20 alkylene which is interrupted by one or more O and/or substituted by OH,    e) a group —CH 2 CH(OH)CH 2 O—R 15 —OCH 2 CH(OH)CH 2 —, —CO—R 16 —CO—, —CO—NH—R 17 —NH—CO— or —(CH 2 ) m —COO—R 18 —OOC—(CH 2 ) m — (in which m is 1 to 3) or                          and if n is 3, R 7  is a group                          and if n is 4, R 7  is a group                          R 8  is C 1 -C 18 alkyl, C 3 -C 18 alkenyl, C 3 -C 20 alkyl which is interrupted by one or more O, N or S and/or substituted by OH, C 1 -C 4 alkyl which is substituted by —P(O)(OR 14 ) 2 , —N(R 9 )(R 10 ) or —OCOR 11  and/or OH, C 3 -C 18 alkenyl, glycidyl or C 7 -C 11 phenylalkyl,    R 9  and R 10  independently of one another are C 1 -C 12 alkyl, C 3 -C 12 alkoxyalkyl, C 4 -C 16 dialkylaminoalkyl or C 5 -C 12 cycloalkyl, or R 9  and R 10  together are C 3 -C 9 alkylene or C 3 -C 9 oxaalkylene or C 3 -C 9 azaalkylene,    R 11  is C 1 -C 18 alkyl, C 2 -C 18 alkenyl or phenyl,    R 12  is C 1 -C 18 alkyl, C 2 -C 18 alkenyl, phenyl, C 1 -C 12 alkoxy, phenoxy, C 1 -C 12 alkylamino or C 6 -C 12 arylamino or a group —R 24 —COOH or —NH—R 17 —NCO,    R 13  is C 1 -C 12 alkyl, C 6 -C 12 aryl or C 7 -C 14 alkaryl,    R 14  is C 1 -C 12 alkyl or phenyl,    R 15  is C 2 -C 10 alkylene, C 4 -C 50 alkylene which is interrupted by one or more 0, phenylene or a group -phenylene-X-phenylene- in which X is —O—, —S—, —SO 2 —, —CH 2 — or —C(CH 3 ) 2 —,    R 16  is C 2 -C 10 alkylene, C 2 -C 10 oxaalkylene or C 2 -C 10 thiaalkylene, C 6 -C 12 arylene or C 2 -C 6 alkenylene,    R 17  is C 2 -C 10 alkylene, phenylene, tolylene, diphenylenemethane or a group                          R 18  is C 2 -C 10 alkylene or C 4 -C 20 alkylene which is interrupted by one or more O,    R 19  is C 3 -C 12 alkanetriyl,    R 20  is C 4 -C 12 alkanetetryl,    R 23  is C 2 -C 10 alkylene, phenylene or a group                           wherein X is O, S, SO 2 , CH 2  or C(CH 3 ) 2 , and    R 24  is C 2 -C 14 alkylene, vinylene or o-phenylene.    
     
     
         2 . An organic material according to  claim 1 , wherein the triazine compound (b) is a compound of the formula I in which n is 1 to 4, R 1  and R 2  independently of one another are H, OH or C 1 -C 4 alkyl, R 3  and R 4  independently of one another are H, OH, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen or a radical —OR 7 , R 5  and R 6  independently of one another are H or C 1 -C 4 alkyl, 
 R 7 , if n is 1, is a) C 1 -C 18 alkyl which is substituted by one or more of the groups OH, C 1 -C 18 alkoxy, allyloxy, phenoxy, furyloxy,  
                     
  —COOR 8 , —CON(R 9 )(R 10 ) and/or by —OCOR 11 ,  
 b) C 4 -C 50 alkyl which is interrupted by one or more O and can be substituted by OH or/and glycidyloxy,  
 c) allyl, glycidyl or benzyl,  
 d) cyclohexyl or hydroxycyclohexyl,  
 and if n is 2, R 7  is C 4 -C 12 alkenylene, C 4 -C 6 alkenylene, xylylene, C 3 -C 20 alkylene which is interrupted by one or more O and/or substituted by OH, or R 7  is a group —CH 2 CH(OH)CH 2 O—R 15 —OCH 2 CH(OH)CH 2 —, —CO—R 16 —CO—, —CH 2 —COO—R 18 —OOC—CH 2 — or  
                     
 and if n is 3, R 7  is a group  
                     
 and if n is 4, R 7  is a group  
                     
 R 8  is C 1 -C 12 alkyl, C 3 -C 18 alkenyl, C 3 -C 20 alkyl which is interrupted by one or more O and/or substituted by OH or R 8  is C 1 -C 4 alkyl which is substituted by —P(O)(OR 14 ) 2 ,  
 R 9  and R 10  are C 1 -C 6 alkyl or R 9  and R 10  together are pentamethylene or 3-oxapentamethylene,  
 R 11  is C 1 -C 12 alkyl, C 2 -C 5 alkenyl or phenyl,  
 R 14  is C 1 -C 14 alkyl,  
 R 15  is C 2 -C 8 alkylene, C 4 -C 50 alkylene which is interrupted by one or more 0, or is a group  
                     
 R 16  is C 2 -C 8 alkylene, C 2 -C 6 oxaalkylene or C 2 -C 6 thiaalkylene and R 18  is C 4 -C 8 alkylene or C 4 -C 12 alkylene which is interrupted by one or more O.  
 
     
     
         3 . An organic material according to  claim 1 , wherein the triazine compound (b) is a compound of the formula I in which n is 1, 2 or 4, R 1  and R 2  independently of one another are H or CH 3 , R 3  and R 4  independently of one another are H, CH 3  or C 1 , R 5  and R 6  are hydrogen, 
 R 7 , if n is 1, is a) C 1 -C 14 alkyl which is substituted by one or more of the groups OH, C 1 -C 15 alkoxy, allyloxy, phenoxy, furyloxy,                           —COOR 8 , —CON(R 9 )(R 10 ) and/or by —OCOR 11 ,    b) C 6 -C 45 alkyl which is interrupted by one or more O and can be substituted by OH or/and glycidyloxy,    c) glycidyl or    d) hydroxycyclohexyl,    and if n is 2, R 7  is C 6 -C 12 alkenylene, 2-butenylene-1,4, xylylene, C 3 -C 20 alkylene which is interrupted by one or more O or substituted by OH, or R 7  is a group —CH 2 CH(OH)CH 2 O—R 15 —OCH 2 CH(OH)CH 2 —, —CO—R 16 —CO—, —CH 2 —COO—R 18 —OOC—CH 2 — or                          and if n is 4, R 7  is                          R 8  is C 4 -C 10 alkyl, oleyl, C 3 -C 20 alkyl which is interrupted by one or more O and/or substituted by OH, or R 8  is —CH 2 P(O)(OR 14 ) 2 ,    R 9  and R 10  are C 2 -C 6 alkyl    R 11  is C 6 -C 10 alkyl, C 2 -C 3 alkenyl    R 14  is C 1 -C 14 alkyl,    R 15  is C 2 -C 8 alkylene, C 10 -C 45 alkylene which is interrupted by more than one 0, or is a group                          R 16  is C 4 -C 8 alkylene and R 18  is C 4 -C 8 alkylene.    
     
     
         4 . An organic material according to  claim 1 , wherein the component (b) is a compound of the formula I in which n is 1 or 2 and, if n is 0.1, R 7  is a group —CH 2 CH(OH)CH 2 —OR 2 , in which R 21  is C 1 -C 18 alkyl, allyl, phenyl, furyl, C 6 -C 12 alkanoyl or C 3 -C 5 alkenoyl and, if n is 2, R 7  is a group —CH 2 CH(OH)CH 2 O—R 15 —OCH 2 CH(OH)CH 2 — in which R 15  is as defined in  claim 1 .  
     
     
         5 . An organic material according to  claim 1 , wherein the component (b) is a compound of the formula I in which R 1  and R 2  are hydrogen or methyl, R 3  and R are hydrogen, chlorine or methyl and R 5  and R 6  are hydrogen.  
     
     
         6 . An organic material according to  claim 1 , wherein the component (a) is a compound containing at least one group of the formula  
       
         
           
           
               
               
           
         
       
       in which R is hydrogen or methyl.  
     
     
         7 . An organic material according to  claim 6 , wherein R is hydrogen.  
     
     
         8 . An organic material according to  claim 6 , wherein the component (a) is one of the following compounds: 
 Di-(2,2,6,6-tetramethylpiperidin-4-yl) succinate,    Di-(2,2,6,6-tetramethylpiperidin-4-yl) sebacate,    Di-(1,2,2,6,6-pentamethylpiperidin-4-yl) sebacate,    Di-(1,2,2,6,6-pentamethylpiperidin-4-yl) butyl-(3,5-di-tert-butyl-4-hydroxybenzyl)-malonate,    Di-(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate,    Tetra-(2,2,6,6-tetramethylpiperidin-4-yl) butane-1,2,3,4-tetracarboxylate,    Tetra-(1,2,2,6,6-pentamethylpiperidin-4-yl) butane-1,2,3-,4-tetracarboxylate,    N-(2,2,6,6-Tetramethylpiperidin-4-yl)-o-aminopropionic acid dodecyl ester,    N-(1-Octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-N′-dodecyl-oxalamide    N-(2,2,6,6-Tetramethylpiperidin-4-yl)-x-dodecylsuccinimide,    2,2,4,4-Tetramethyl-7-oxa-3,20-diaza-21-oxo-dispiro[5.1.11.2]heneicosane,    8-Acetyl-3-dodecyl-1,3,8-triaza-7,7,9,9-tetrarethylspiro[4.5]decane-2,4-dione,    20-(Dodecyloxycarbonylethyl)-2,2,4,4-tetramethyl-7-oxa-3,20-diaza-21-oxo-dispiro-[5.1.11.2]heneicosane,    or a compound of the formulae                                                                  
     
     
         9 . An organic material according to  claim 1 , which contains 0.01 to 5% by weight of the component (a) and 0.02 to 5% by weight of the component (b), relative to the material.  
     
     
         10 . An organic material according to  claim 9 , which contains 0.02 to 2% by weight of the component (a) and 0.05 to 3% by weight of the component (b).  
     
     
         11 . An organic material according to  claim 1 , wherein the material is an organic polymer.  
     
     
         12 . An organic polymer according to  claim 11 , which, in addition to the components (a) and (b) also contains further stabilizers, fillers, reinforcing agents, pigments, dyes, plasticizers, solvents, lubricants, flow-control agents, fluorescent brighteners, nucleating agents, antistatic agents or fire-retarding agents.  
     
     
         13 . An organic polymer according to  claim 11 , wherein the polymer is a coating binder.  
     
     
         14 . An organic material according to  claim 1 , wherein the material is a radiation-curable coating material.  
     
     
         15 . A radiation-curable coating material containing a hydroxyphenyltriazin of formula I as defined in  claim 1  in the absence of a sterically hindered amine.  
     
     
         16 . A process for stabilizing organic material against damage caused by light, heat and oxygen by the addition of the components (a) and (b) as defined in  claim 1 .  
     
     
         17 . A compound of the formula Ia  
       
         
           
           
               
               
           
         
         in which n is 1 to 4,  
         R 1  and R 2  independently of one another are H, OH, C 1 -C 12 alkyl, cyclohexyl or trifluoromethyl,  
         R 3  and R 4  independently of one another are H, OH, C 1 -C 12 alkyl, cyclohexyl, C 1 -C 18 alkoxy or halogen and, in the event that n=1, can also be a radical —OR 7 ,  
         R 5  and R 6  independently of one another are H, C 1 -C 12 alkyl or halogen,  
         R 7 , if n is 1, is a) C 1 -C 12 alkyl which is substituted by phenoxy (which is unsubstituted or substituted by C 1 -C 18 alkyl, C 1 -C 18 alkoxy or halogen) or by a group —COOR 8 , —CONH 2 , —CONHR 9 , —CON(R 9 )(R 10 ), —NH 2 , NHR 9 , —N(R 9 )(R 10 ) or —O—CO—R 22 ,  
         b) C 4 -C 50 alkyl which is interrupted by more than one O and can be substituted by OH or/and glycidyloxy,  
         c) glycidyl or a group  
         
           
             
             
                 
                 
             
           
         
         d) cyclohexyl substituted by OH or —COR 11    
         e) a group —CH 2 CH(OH)CH 2 OR 21    
         f) a group —SO 2 —R 13 ,  
         g) a group —CO—R 12    
         and if n is 2, R 7  is  
         a) C 2 -C 12 alkylene,  
         b) C 4 -C 12 alkenylene,  
         c) xylylene,  
         d) C 3 -C 20 alkylene which is interrupted by one or more 0 and/or substituted by OH,  
         e) a group —CH 2 CH(OH)CH 2 O—R 15 —OCH 2 CH(OH)CH 2 —, —(CH 2 ) m —COO—R 18 —OOC—(CH 2 ) m — (wherein m is 1-3) or  
         
           
             
             
                 
                 
             
           
         
         and if n is 3, R 7  is a group  
         
           
             
             
                 
                 
             
           
         
          (wherein m is 1-3),  
         and if n is 4, R 7  is a group  
         
           
             
             
                 
                 
             
           
         
          (wherein m is 1-3),  
         R 8  is C 3 -C 20 alkyl which is interrupted by one or more O, N or S and can be substituted by OH, or R 8  is C 1 -C 4 alkyl which is substituted by —P(O)(OR 14 ) 2 , —N(R.) 10 ), or —OCOR 11  and/or OH, or R 8  is C 3 -C 18 alkenyl, glycidyl or C 7 -C 11 phenylalkyl,  
         R 9  and R 10  independently are C 1 -C 12 alkyl, C 3 -C 12 alkoxyalkyl, C 4 -C 16 dialkylaminoalkyl or C 5 -C 12 cycloalkyl, or R 9  and R 10  together are C 3 -C 9 alkylene or C 3 -C 9 -oxaalkylene or C 3 -C 9 azaalkylene,  
         R 11  is C 1 -C 18 alkyl, C 2 -C 18 alkenyl or phenyl,  
         R 12  is a group —R 24 —COOH or —NH—R 17 —NCO,  
         R 13  is C 1 -C 12 alkyl, C 6 -C 12 aryl or C 7 -C 14 alkaryl  
         R 14  is C 1 -C 12 alkyl or phenyl  
         R 15  is C 2 -C 10 alkylene, C 4 -C 50 alkylene which is interrupted by one or more 0, or R 15  is phenylene or a group -phenylene-X-phenylene in which X is —O—, —S—, —SO 2 —, —CH 2 — or —C(CH 3 ) 2 — 
         R 17  is C 2 -C 10 alkylene, phenylene, tolylene, diphenylenemethane or a group  
         
           
             
             
                 
                 
             
           
         
         R 18  is C 2 -C 10 alkylene or C 4 -C 20 alkylene which is interrupted by one or more O.  
         R 19  is C 3 -C 12 alkanetriyl,  
         R 20  is C 4 -C 12 alkanetetryl,  
         R 21  is H, C 1 -C 18 alkyl, C 3 -C 18 alkenyl, phenyl, phenyl substituted by C 1 -C 12 alkyl, C 1 -C 12 alkoxy or halogen, or R 21  is C 2 -C 19 alkanoyl, benzoyl, C 3 -C 18 alkenoyl, furyl or a group  
         
           
             
             
                 
                 
             
           
         
         R 22  is C 2 -C 5 alkenyl,  
         R 23  is C 2 -C 10 alkylene, phenylene or a group  
         
           
             
             
                 
                 
             
           
         
          wherein X is O, S, SO 2 , CH 2  or C(CH 3 ) 2 , and  
         R 24  is C 2 -C 14 alkylene, vinylene or o-phenylene.  
       
     
     
         18 . A compound of the formula Ia according to  claim 17 , 
 in which n is 1 or 2,    R 1  and R 2  independently of one another are H, OH, C 1 -C 12 alkyl or halogenomethyl,    R 3  and R 4  independently of one another are H, OH, C 1 -C 12 alkyl, C 1 -C 18 alkoxy or halogen and, in the event that n=1, can also be a radical —OR 7 ,    R 5  and R 6  independently of one another are H, C 1 -C 12 alkyl or halogen,    R 7  is C 1 -C 12 alkyl which is substituted by phenoxy which is unsubstituted or substituted by C 1 -C 18 alkyl, C 1 -C 18 alkoxy or halogen, C 1 -C 12 alkyl which is substituted by —COOR 8 , —CONH 2 , —CONHR 9 , —CON(R 9 )(R 10 ), —NH 2 , —NHR 9  or —N(R 9 )(R 10 ), C 6 -C 20 alkyl which is interrupted by more than one O and is substituted by OH, glycidyl, cyclohexyl substituted by OH or —OCOR 11 , a group —CH 2 CH(OH)CH 2 OR 19  or —SO 2 R 13 , if n is 1, and, if n is 2, is C 2 -C 12 alkylene, C 4 -C 12 alkenylene, xylylene, C 3 -C 20 alkylene which is interrupted by O and/or substituted by OH, or a group CH 2 CH(OH)CH 2 O—R 15 —OCH 2 CH(OH)CH 2 — or —(CH 2 ) m —COO—R 18 —OOC—(CH 2 ) m — in which m is 1-3,    R 8  is C 3 -C 20 alkyl which is interrupted by O, N or S and/or substituted by OH, C 1 -C 4 alkyl which is substituted by —P(O)(OR 14 ) 2 , —N(R 9 )(R 10 ) or —OCOR 11  and/or —OH, C 3 -C 18 alkenyl, glycidyl or C 7 -C 11 phenylalkyl,    R 9  and R 10  independently of one another are C 1 -C 12 alkyl, C 3 -C 12 alkoxyalkyl, C 4 -C 16 dialkylaminoalkyl or C 5 -C 12 cycloalkyl, or R 9  and R 10  together are C 3 -C 9 alkylene or C 3 -C 9 oxaalkylene or C 3 -C 9 azaalkylene,    R 11  is C 1 -C 18 alkyl, C 2 -C 16 alkenyl or phenyl,    R 13  is C 1 -C 12 alkyl, C 6 -C 12 aryl or C 7 -C 14 alkaryl,    R 14  is C 1 -C 12 alkyl or phenyl,    R 15  is C 2 -C 10 alkylene, phenylene or a group -phenylene-X-phenylene in which X is —O—, —S—, —SO 2 —, —CH 2 — or —C(CH 3 ) 2 ,    R 18  is C 2 -C 10 alkylene or C 4 -C 20 alkylene which is interrupted by O, and    R 19  is C 1 -C 18 alkyl, phenyl, phenyl which is substituted by C 1 -C 12 alkyl, C 1 -C 12 alkoxy or halogen, C 2 -C 12 alkanoyl, benzoyl or C 3 -C 5 alkenoyl.    
     
     
         19 . A compound according to  claim 17  of the formula Ia in which n is 1 to 4, R 1  and R 2  independently of one another are H, OH or C 1 -C 4 alkyl, R 3  and R 4  independently of one another are H, OH, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen or a radical —OR 7 , R 5  and R 6  independently of one another are H or C 1 -C 4 alkyl, 
 R 7 , if n is 1, is C 1 -C 6 alkyl which is substituted by —COOR 8 , —COONHR 9 , —CON(R 9 )(R 10 ) or —OCOR 22 , or R 7  is glycidyl, hydroxycyclohexyl or a group —CH 2 CH(OH)CH 2 OR 21 , and if n is 2, R 7  is C 4 -C 12 alkylene, C 4 -C 6 alkenylene, xylylene, C 3 -C 20 alkylene which is interrupted by one or more O and/or substituted by OH, or R 7  is a group —CH 2 CH(OH)CH 2 O—R 15 —OCH 2 CH(OH)CH 2 —, —CH 2 —COO—R 18 —OOCCH 2 — or  
                     
 and if n is 3, R 7  is a group  
                     
 and if n is 4, R 7  is a group  
                     
 R 8  is C 3 -C 20 alkyl which is interrupted by one or more O and can be substituted by OH or R 8  is C 1 -C 4 alkyl which is substituted by —P(O)(OR 14 ) 2  or R 8  is C 3 -C 18 alkenyl,  
 R 9  and R 10  independently are C 1 -C 8 alkyl or cyclohexyl or R 9  and R 10  together are pentamethylene or 3-oxapentamethylene,  
 R 14  is C 1 -C 14 alkyl,  
 R 15  is C 2 -C 8 alkylene, C 4 -C 50 alkylene which is interrupted by one or more 0, or R 15  is a group -phenylene-X-phenylene- in which X is —O—, —CH 2 — or —C(CH 3 ) 2 —,  
 R 18  is C 4 -C 8 alkylene or C 4 -C 12 alkylene which is interrupted by one or more 0,  
 R 21  is H, C 4 -C 18 alkyl, allyl, phenyl, furyl, C 5 -C 19 alkanoyl or C 3 -C 5 alkenoyl and R 22  is C 2 -C 5 alkenyl.  
 
     
     
         20 . A compound according to  claim 17  of the formula Ia in which n is 1 or 2, R 1  and R 2  independently of one another are H or CH 3 , R 3  and R 4  independently of one another are H, CH 3  or C 1 , R 5  and R 6  are hydrogen, 
 R 7 , if n is 1, is C 1 -C 4 alkyl which is substituted by —COOR 8 , —CON(R 9 )(R 10 ) or —O—COR 22 , or R 7  is glycidyl, 2-hydroxycyclohexyl or a group —CH 2 CH(OH)CH 2 OR 21 ,  
 and if n is 2, R 7  is C 6 -C 12 alkenylene, 2-butene-1,4-ylene, xylylene or C 3 -C 20 alkylene which is interrupted by one or more O and/or substituted by OH, or R 7  is a group —CH 2 CH(OH)CH 2 O—R 18 —OCH 2 CH(OH)CH 2 —, —CH 2 —COO—R 18 —OOCCH 2 — or  
                     
 and if n is 4, R 7  is a group  
                     
 R 8  is C 3 -C 20 alkyl which is interrupted by one or more O and can be substituted by OH or R 8  is —CH 2 P(O)(OR 14 ) 2  or oleyl  
 R 9  and R 10  are C 2 -C 6 alkyl  
 R 15  is C 2 -C 8 alkylene, C 10 -C 45 alkylene which is interrupted by one or more 0 or is a group  
                     
 R 18  is C 4 -C 8 alkylene,  
 R 21  is H, C 4 -C 15 alkyl, allyl, phenyl, furyl, C 5 -C 12 alkanoyl or C 3 -C 5 alkenoyl  
 and R 22  is C 2 -C 3 alkenyl.  
 
     
     
         21 . A compound according to  claim 17  of the formula Ia in which n is 2.  
     
     
         22 . A process for stabilizing organic material, in particular organic polymers, against damage caused by light, heat and-oxygen, by the addition of an o-hydroxyphenyl triazine, which comprises adding at least one compound of the formula Ia according to  claim 15 .  
     
     
         23 . An organic material containing at least one compound of the formula Ia according to  claim 17  as a stabilizer against damage caused by light, heat and oxygen.  
     
     
         24 . An organic polymer as a material according to  claim 23 .  
     
     
         25 . An organic material according to  claim 23 , containing 0.01 to 10% by weight of a compound of the formula Ia, relative to the material.  
     
     
         26 . A polycarbonate according to  claim 24 .  
     
     
         27 . An organic material according to  claim 23  which is a radiation-curable coating material.  
     
     
         28 . The use of the compounds of  claim 17  of the formula Ia as a stabilizer for organic materials, in particular for organic polymers.  
     
     
         29 . Use according to  claim 28  as a stabilizer for polycarbonates.  
     
     
         30 . The use of the compounds of  claim 17  of the formula Ia as stabilizer for radiation-curable coating material.