Piperidine-based stabilizers and polymers end-capped with the same

Abstract

The invention relates to piperidine-based compounds of formula (I) that are used to improve UV, thermal, and thermo-oxidative stability of high performance aromatic polymers in a blend or as end-cappers of the same polymers.

1 - 15 : (canceled) 
     
     
         16 . An end-capper stabilizer compound (EC) of formula (I): 
       
         
           
           
               
               
           
         
         wherein: 
         R k  is selected from the group consisting of —H, aliphatic groups, and alkoxy groups, and 
         R j  groups are equal to or different from each other and from R k  and are independently selected from aliphatic groups, and 
         Y is a monovalent group selected from a first group consisting of a halogen, a carboxylic ester, an acid halide, an anhydride, an amide, and a thioester or from a second group consisting of a hydroxyl, an amine, a carboxylic acid, a thiol, and any protected derivative thereof, and 
         A is a divalent group of the general formula (II): 
       
       
         
           
           
               
               
           
         
         wherein: 
         n is 0, 1 or 2, and 
         R i  are independently in an ortho or meta position and selected from the group consisting of —H, —NO 2 , alkyl groups, perfluorinated groups, aryl groups, aryl amine groups, aryl ether groups, aryl sulfone groups, aryl thioether groups, and fused aryl ring systems, and 
         Q is a divalent group selected from the group consisting of a bond, —CH 2 —, —O—, —C≡C—, —CH═CH—, —C(CH 3 ) 2 —, —NH—, —S—, —C(Cl) 2 —, —C(F) 2 —, —C(CF 3 ) 2 —, —N(CH 3 )—, —C(═CCl 2 )—, —SO 2 — and (cyclo)alkyl groups. 
       
     
     
         17 . The end-capper stabilizer compound (EC) according to  claim 16 , wherein said divalent group A is 
       
         
           
           
               
               
           
         
       
     
     
         18 . A method for making the end-capper stabilizer compound (EC) according to  claim 16 , comprising the step of reacting compounds of formulae (III) and (IV) together in the presence of a base; 
       
         
           
           
               
               
           
         
         wherein: 
         R k  is selected from the group consisting of —H, aliphatic groups, and alkoxy groups, and 
         R j  groups are equal to or different from each other and from R k  and are independently selected from aliphatic groups, and 
         Z is a halogen, and 
         Y is a monovalent group selected from a first group consisting of a halogen, a carboxylic ester, an acid halide, an anhydride, an amide, and a thioester or from a second group consisting of a hydroxyl, an amine, a carboxylic acid, a thiol, and any protected derivative thereof, and 
         A is a divalent group of the general formula (II): 
       
       
         
           
           
               
               
           
         
         wherein: 
         n is 0, 1 or 2, and 
         R i  are independently in an ortho or meta position and selected from the group consisting of —H, —NO 2 , alkyl groups, perfluorinated groups, aryl groups, aryl amine groups, aryl ether groups, aryl sulfone groups, aryl thioether groups, and fused aryl ring systems, and 
         Q is a divalent group selected from the group consisting of a bond, —CH 2 —, —O—, —C≡C—, —CH═CH—, —C(CH 3 ) 2 —, —NH—, —S—, —C(F) 2 —, —C(CF 3 ) 2 —, —N(CH 3 )—, —C(═CCl 2 )—, —SO 2 — and (cyclo)alkyl groups. 
       
     
     
         19 . The method of  claim 18 , wherein the reaction is carried out in a polar aprotic solvent. 
     
     
         20 . An end capped polymer (EP) comprising recurring units and at least two chain ends, wherein at least one of the chain ends comprises formula (V): 
       
         
           
           
               
               
           
         
         wherein: 
         R k  is selected from the group consisting of —H, aliphatic groups, and alkoxy groups, and 
         R j  groups are equal to or different from each other and from R k  and are independently selected from aliphatic groups, and 
         X is a divalent group selected from the group consisting of —O—, —(C═O)—NH—, —(C═O)—, —(C═O)—O—, —(C═O)—S—, —NH— and —S—, and 
         A is a divalent group of the general formula (II): 
       
       
         
           
           
               
               
           
         
         wherein: 
         n is 0, 1 or 2, and 
         R i  are independently in an ortho or meta position and selected from the group consisting of —H, —NO 2 , alkyl groups, perfluorinated groups, aryl groups, aryl amine groups, aryl ether groups, aryl sulfone groups, aryl thioether groups, and fused aryl ring systems, and 
         Q is a divalent group selected from the group consisting of a bond, —CH 2 —, —O—, —C≡C—, —CH═CH—, —C(CH 3 ) 2 —, —NH—, —S—, —C(F) 2 —, —C(CF 3 ) 2 —, —N(CH 3 )—, —C(═CCl 2 )—, —SO 2 — and (cyclo)alkyl groups. 
       
     
     
         21 . The end capped polymer (EP) according to  claim 20 , wherein said divalent group A is 
       
         
           
           
               
               
           
         
       
     
     
         22 . A method for making the end capped polymer (EP) according to  claim 20  comprising the step of reacting an end-capper stabilizer compound (EC) of formula (I): 
       
         
           
           
               
               
           
         
         wherein: 
         R k  is selected from the group consisting of —H, aliphatic groups, and alkoxy groups, and 
         R j  groups are equal to or different from each other and from R k  and are independently selected from aliphatic groups, and 
         Y is a monovalent group selected from a first group consisting of a halogen, a carboxylic ester, an acid halide, an anhydride, an amide, and a thioester or from a second group consisting of a hydroxyl, an amine, a carboxylic acid, a thiol, and any protected derivative thereof, and 
         A is a divalent group of the general formula (II): 
       
       
         
           
           
               
               
           
         
         wherein: 
         n is 0, 1 or 2, and 
         R i  are independently in an ortho or meta position and selected from the group consisting of —H, —NO 2 , alkyl groups, perfluorinated groups, aryl groups, aryl amine groups, aryl ether groups, aryl sulfone groups, aryl thioether groups, and fused aryl ring systems, and 
         Q is a divalent group selected from the group consisting of a bond, —CH 2 —, —O—, —C≡C—, —CH═CH—, —C(CH 3 ) 2 —, —NH—, —S—, —C(F) 2 —, —C(CF 3 ) 2 —, —C(═CCl 2 )—, —SO 2 — and (cyclo)alkyl groups, 
         with at least: 
         a polymer comprising at least one reactive chain end, or 
         a monomer comprising at least one reactive group, 
         wherein the at least one reactive chain end or the at least one reactive group is able to react with the monovalent group Y of the general structural formula (I). 
       
     
     
         23 . The method according to  claim 22 , wherein the at least one reactive chain end or the at least one reactive group is selected from a first group consisting of a halogen, a carboxylic ester, an acid halide, an anhydride, an amide, and a thioester or from a second group consisting of a hydroxyl, an amine, a carboxylic acid, a thiol, and any protected derivative thereof. 
     
     
         24 . The method according to  claim 23 , wherein the at least one reactive chain end or the at least one reactive group is a halogen and the monovalent group Y of the end-capper stabilizer compound (EC) is a hydroxyl. 
     
     
         25 . A polymer composition (C) comprising at least one end-capper stabilizer compound (EC) according to  claim 16  and at least one polymer (P*). 
     
     
         26 . The polymer composition (C) according to  claim 25 , wherein the polymer (P*) is selected from the group consisting of polyolefins, polyesters, polyethers, polyketones, poly(etherketone)s, poly(ethersulfone)s, polyamides, polyurethanes, polystyrenes, polyacrylates, polymethacrylates, polyacetals, polytetrafluoroethylene, polyvinylidene fluoride, polyacrylonitriles, polybutadienes, acrylonitrile butadiene styrene, styrene acrylonitrile, acrylate styrene acrylonitrile, cellulosic acetate butyrate, cellulosic polymers, polyimides, polyamideimides, polyetherimides, polyphenylsulfides, polyphenylene oxides, polyvinylchlorides, polyvinylbutyrates, polycarbonates, epoxy resins, polysiloxanes, and polyketimines. 
     
     
         27 . The polymer composition (C) according to  claim 25 , wherein the polymer composition (C) further comprises at least one ingredient selected from the group consisting of dyes, pigments, fillers, UV stabilizers, light stabilizers, optical brighteners, and mixtures thereof. 
     
     
         28 . A method for stabilizing a polymer comprising adding at least one stabilizing compound (EC) according to  claim 16  to at least one polymer (P*). 
     
     
         29 . The method of  claim 28 , wherein the at least one stabilizing compound (EC) acts as an acid scavenger for the at least one polymer (P*). 
     
     
         30 . An article comprising the polymer composition (C) according to  claim 25 . 
     
     
         31 . A polymer composition (C) comprising at least one end capped polymer (EP) of  claim 20  and at least one polymer (P*). 
     
     
         32 . A method for stabilizing a polymer comprising adding at least one end capped polymer (EP) according to  claim 20  to at least one polymer (P*). 
     
     
         33 . The method of  claim 32 , wherein the at least one end capped polymer (EP) acts as an acid scavenger for the at least one polymer (P*).