Polymer additives with improved permanence and surface affinity

Abstract

Novel stabilizers that are comprised of known polymer additive moieties chemically bound to hyperbranched and/or dendritic polymers or copolymers, and novel stabilizers comprised of known polymer additive moieties chemically bound to amphiphilic copolymers exhibit superior permanence in an organic substrate as well as high surface affinity.

What is claimed is:  
     
         1 . A permanent or surface-active hyperbranched or dendritic stabilizer comprised of at least one polymer additive moiety and at least one hyperbranched or dendritic polymer moiety.  
     
     
         2 . A stabilizer according to  claim 1  which is a hyperbranched or dendritic polymer or copolymer of the formula (I)  
       
         
           
             
               
                 
                   
                     
                       
                         ( 
                         
                           
                             
                               additive 
                             
                           
                           
                             
                               moiety 
                             
                           
                         
                         ) 
                       
                       x 
                     
                      
                     
                       
                         — 
                          
                         
                           ( 
                           L 
                           ) 
                         
                       
                       y 
                     
                      
                     
                       
                         — 
                          
                         
                           ( 
                           
                             
                               
                                 
                                   hyperbranched 
                                    
                                   
                                       
                                   
                                    
                                   or 
                                 
                               
                             
                             
                               
                                 
                                   dendritic 
                                    
                                   
                                       
                                   
                                    
                                   polymer 
                                 
                               
                             
                             
                               
                                 
                                   or 
                                    
                                   
                                       
                                   
                                    
                                   copolymer 
                                    
                                   
                                       
                                   
                                    
                                   moiety 
                                 
                               
                             
                           
                           ) 
                         
                       
                       z 
                     
                   
                 
                 
                   
                     ( 
                     I 
                     ) 
                   
                 
               
             
           
           
           
               
           
         
         where  
         x and y are each independently greater than or equal to 1,  
         z is 1 to 5, and  
         L is independently of each other a direct bond or a chemical linking group,  
         with the proviso that the reaction product of the self-condensation product of 3,5-dihydroxybenzoic acid and 4-hydroxyphenylmethyl carbinol benzotriazole is excluded.  
       
     
     
         3 . A stabilizer according to  claim 2  in which the additive moiety is selected from the group consisting of antioxidant, ultraviolet light absorber, hindered amine light stabilizer, hydroxylamine stabilizer, nitrone stabilizer, amine oxide stabilizer, benzofuranone stabilizer and organic phosphorus stabilizer moieties.  
     
     
         4 . A stabilizer according to  claim 2  in which x is greater than one and comprising two different additive moieties.  
     
     
         5 . A stabilizer according to  claim 4  in which the two different additive moieties are the ultraviolet light absorber and hindered amine light stabilizer moieties.  
     
     
         6 . A stabilizer according to  claim 2  in which the hyperbranched or dendritic moiety comprises a multi-functional monomer selected from dimethylolpropionic acid and α,α-bis(hydroxymethyl)butyric acid.  
     
     
         7 . A stabilizer according to  claim 2  in which the linking group L is —OCO— or —COO— or is a hydrocarbylene comprising the groups —OCO— or —COO—.  
     
     
         8 . A process for the preparation of a compound of formula (I)  
       
         
           
             
               
                 
                   
                     
                       
                         ( 
                         
                           
                             
                               additive 
                             
                           
                           
                             
                               moiety 
                             
                           
                         
                         ) 
                       
                       x 
                     
                      
                     
                       
                         — 
                          
                         
                           ( 
                           L 
                           ) 
                         
                       
                       y 
                     
                      
                     
                       
                         — 
                          
                         
                           ( 
                           
                             
                               
                                 
                                   hyperbranched 
                                    
                                   
                                       
                                   
                                    
                                   or 
                                 
                               
                             
                             
                               
                                 
                                   dendritic 
                                    
                                   
                                       
                                   
                                    
                                   polymer 
                                 
                               
                             
                             
                               
                                 
                                   or 
                                    
                                   
                                       
                                   
                                    
                                   copolymer 
                                    
                                   
                                       
                                   
                                    
                                   moiety 
                                 
                               
                             
                           
                           ) 
                         
                       
                       z 
                     
                   
                 
                 
                   
                     ( 
                     I 
                     ) 
                   
                 
               
             
           
           
           
               
           
         
         which comprises reacting an additive compound of formula (a)  
         (additive moiety) p -(G) q   (a)  
         with a fully formed hyperbranched or dendritic polymer or copolymer,  
         with a partially formed hyperbranched or dendritic polymer or copolymer, or  
         with components of a hyperbranched or dendritic polymer or copolymer,  
         where  
         x and y are each independently greater than or equal to 1,  
         z is 1 to 5, and  
         L is independently of each other a direct bond or a chemical linking group,  
         p and q are independently greater than or equal to 1, and  
         G is independently a reactive functional group (RFG) or a hydrocarbylene comprising  
         at least one reactive functional group.  
       
     
     
         9 . A process according to  claim 8  which comprises reacting a carboxy-functional additive with poly(ethylene glycol)monomethyl ether and dimethylolpropionic acid.  
     
     
         10 . A stabilized composition comprising 
 (i) an organic material subject to the deleterious effects of heat, light or oxidation, and    (ii) an effective stabilizing amount of a stabilizer according to  claim 1 .    
     
     
         11 . A process for stabilizing an organic material against the deleterious effect of heat, light or oxidation, which comprises incorporating therein or applying thereto at least one permanent or surface-active hyperbranched or dendritic stabilizer according to  claim 1 .  
     
     
         12 . A permanent or surface active amphiphilic polymer stabilizer comprised of at least one polymer additive moiety and at least one amphiphilic copolymer moiety.  
     
     
         13 . A stabilizer according to  claim 12  of the formula (II)  
       
         
           
             
               
                 
                   
                     
                       
                         ( 
                         
                           
                             
                               additive 
                             
                           
                           
                             
                               moiety 
                             
                           
                         
                         ) 
                       
                       t 
                     
                      
                     
                       
                         — 
                          
                         
                           ( 
                           L 
                           ) 
                         
                       
                       u 
                     
                      
                     
                       
                         — 
                          
                         
                           ( 
                           
                             
                               
                                 
                                   diblock 
                                    
                                   
                                       
                                   
                                    
                                   amphiphilic 
                                 
                               
                             
                             
                               
                                 moiety 
                               
                             
                           
                           ) 
                         
                       
                       v 
                     
                   
                 
                 
                   
                     ( 
                     II 
                     ) 
                   
                 
               
             
           
           
           
               
           
         
         where t, u and v are independently greater than or equal to 1, and  
         L is independently of each other a direct bond or a chemical linking group.  
       
     
     
         14 . A stabilizer according to  claim 13  in which t, u and v are each 1 and the amphiphilic copolymer moiety is selected from C 18 H 37 (OCH 2 CH 2 ) 2 — and CH 3 CH 2 (CH 2 CH 2 ) 13 CH 2 CH 2 (OCH 2 CH 2 ) 2.5 — and the linking group L comprises an ester group.  
     
     
         15 . A stabilized composition comprising 
 (i) an organic material subject to the deleterious effects of heat, light or oxidation, and    (ii) an effective stabilizing amount of a stabilizer compound of formula (II) according to  claim 12 .    
     
     
         16 . A process for stabilizing an organic material against the deleterious effect of heat, light or oxidation, which comprises incorporating therein or applying thereto at least one permanent or surface active amphiphilic polymer stabilizer according to  claim 12.