Hindered amine light stabilizers

Abstract

A compound of the formula (I), wherein R 1 and R 2 independently of one another are hydrogen, C 1 -C 22 alkyl, —O., —OH, —CH 2 CN, C 1 -C 18 alkoxy, C 2 -C 18 alkoxy substituted by —OH; C 5 -C 12 cycloalkoxy, C 3 -C 6 alkenyl, C 3 -C 6 alkenyloxy, C 7 -C 9 phenylalkyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C 1 -C 4 alkyl; or C 1 -C 8 acyl; and R 3 and R 4 independently of one another are C 1 -C 22 alkyl or a group of the formula (1a), wherein R 0 has one of the meanings of R 1 and R 2 .

1 : A compound of formula (I) 
       
         
           
           
               
               
           
         
         wherein 
         R 1  and R 2  independently of one another are hydrogen, C 1 -C 22 alkyl, —O., —OH, —CH 2 CN, C 1 -C 18 alkoxy, C 2 -C 18 alkoxy substituted by —OH, C 5 -C 12 cycloalkoxy, C 3 -C 6 alkenyl, C 3 -C 6 alkenyloxy, C 7 -C 9 phenylalkyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C 1 -C 4 alkyl; or C 1 -C 8 acyl; and 
         R 3  and R 4  independently of one another are C 1 -C 22 alkyl or a group of formula (Ia) 
       
       
         
           
           
               
               
           
         
         wherein R 0  has one of the meanings of R 1  and R 2 . 
       
     
     
         2 : The compound according to  claim 1 , wherein
 R 1  and R 2  independently of one another are hydrogen, C 1 -C 8 alkyl, C 1 -C 18 alkoxy or cyclohexyloxy; and   R 3  and R 4  independently of one another are C 1 -C 6 alkyl.   
     
     
         3 : The compound according to  claim 1 , wherein the compound of the formula (I) is the compound (A) 
       
         
           
           
               
               
           
         
       
     
     
         4 : A composition comprising:
 an organic material susceptible to degradation induced by light, heat or oxidation, and   the compound according to  claim 1 .   
     
     
         5 : The composition according to  claim 4 , wherein the organic material is a thermoplastic polymer. 
     
     
         6 : The composition according to  claim 4 , wherein the organic material is a polyolefin, an acrylonitrile/butadiene/styrene, a polyvinyl chloride, a polymethylmethacrylate, a polyamide or a polyoxymethylene. 
     
     
         7 : The composition according to  claim 4 , wherein the organic material is a thermoplastic polyolefin. 
     
     
         8 : The composition according to  claim 4 , wherein the organic material is a thermoplastic polyethylene or polypropylene. 
     
     
         9 : The composition according to  claim 4 , further comprising a phenolic antioxidant and/or a phenolic phosphite. 
     
     
         10 : The composition according to  claim 9 , wherein the phenolic antioxidant is pentaerythritol tetrakis[3,5-di-tert-butyl-4-hydroxyphenylpropionate], octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)proprionate, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene, N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylene-diamide or 1,3,5-tris[3,5-di-tert-butyl-4-hydroxybenzyl]isocyanurate, 2,4-di-t-butylphenyl-3,5-di-t-butyl-4-hydroxybenzoate or bis(1,2,2,6,6-pentamethylpiperidin-4-yl)-butyl(3,5-di-t-butyl-4-hydroxybenzyl)malonate), and the phenolic phosphite is tris[2,4-di-tert-butylphenyl]phosphite. 
     
     
         11 : The composition according to  claim 4 , further comprising:
 a sterically hindered amine light stabilizer different from the compound of the formula (I), and/or   an UV-absorber.   
     
     
         12 : The composition according to  claim 11 , wherein the UV-absorber is present and is selected from the group consisting of a 2-(2′-hydroxyphenyl)benzotriazole, a 2-hydroxybenzophenone, an oxamide and a 2-(2-hydroxyphenyl)-1,3,5-triazine. 
     
     
         13 : The composition according to which  claim 4 , further comprising a filler and/or a pigment. 
     
     
         14 : An automotive interior or exterior trim material comprising the composition according to  claim 4 . 
     
     
         15 : The automotive interior or exterior trim material according to  claim 14 , which is a facing material for a roof, seat or dashboard. 
     
     
         16 : An agricultural article comprising the composition according to  claim 4 . 
     
     
         17 : The agricultural article according to  claim 16 , which is a greenhouse cover. 
     
     
         18 : A method for stabilizing an organic material against degradation induced by light, heat or oxidation, comprising incorporating into said organic material at least one compound of  claim 1 . 
     
     
         19 : A method for preparing a compound of  claim 1 , comprising reacting a compound of formula (II) 
       
         
           
           
               
               
           
         
         with pyrrolidine in an organic solvent, optionally in the presence of an organic or inorganic base.