Methods for producing and purifying 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine monomers and polycarbonates derived therefrom

Abstract

Disclosed herein is a method for producing a 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine. The method comprises forming a reaction mixture comprising at least one substituted or unsubstituted phenolphthalein compound, at least one substituted or unsubstituted primary hydrocarbyl amine, and an acid catalyst; and heating the reaction mixture to form 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine. An adduct of the 2-hydrocarbyl-3,3-bis(4-hydroxyaryl) phthalimidine is formed either by using an excess of the primary hydrocarbyl amine in the first heating step, or by isolating crude 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine after the heating step and then reacting with a further amount of the primary hydrocarbyl amine. The 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine has a formula: where R 1 is selected from the group consisting of a hydrogen and a hydrocarbyl group, and R 2 is selected from the group consisting of a hydrogen, a hydrocarbyl group, and a halogen.

1 . A polymer comprising structural units derived from a 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine prepared by a method comprising heating a reaction mixture comprising:
 (i) a primary hydrocarbyl amine of Formula (II),
   R 1 NH 2   (II), 
   (ii) a phenolphthalein compound of Formula (III),   
     
       
         
         
             
             
         
       
     
     wherein R 1  is selected from a group consisting of a hydrogen and a hydrocarbyl group, R 2  is selected from the group consisting of a hydrogen, a hydrocarbyl group, and a halogen, and R 3  is selected from the group consisting of a hydrogen and a hydrocarbyl group; and forming said 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine, wherein the hydrocarbyl group is selected from the group consisting of an alkyl group, a cycloalkyl group, and an aryl group;
 (B) forming an adduct of said 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine and said primary hydrocarbyl amine; 
 (C) precipitating said adduct; and 
 (D) decomposing said adduct to produce said 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine. 
 
   
   
       2 . The polymer of  claim 1 , wherein said polymer is selected from the group consisting of homopolymers and copolymers of a polycarbonate, a polyestercarbonate, a polyester, a polyesteramide, a polyimide, a polyetherimide, a polyamideimide, a polyether, a polyethersulfone, a polycarbonate—polyorganosiloxane block copolymer, a copolymer comprising aromatic ester, estercarbonate, and carbonate repeat units; and a polyetherketone. 
   
   
       3 . A polymer blend comprising at least one thermoplastic polymer and the polycarbonate of  claim 2 . 
   
   
       4 . The polymer blend of  claim 3 , wherein said at least one thermoplastic polymer is selected from the group consisting of vinyl polymers, acrylic polymers, polyacrylonitrile, polystyrenes, polyolefins, polyesters, polyurethanes, polyamides, polysulfones, polyimides, polyetherimides, polyphenylene ethers, polyphenylene sulfides, polyether ketones, polyether ether ketones, ABS resins, polyethersulfones, poly(alkenylaromatic) polymers, polybutadiene, polyacetals, polycarbonates, polyphenylene ethers, ethylene-vinyl acetate copolymers, polyvinyl acetate, liquid crystal polymers, ethylene-tetrafluoroethylene copolymer, aromatic polyesters, polyvinyl fluoride, polyvinylidene fluoride, polyvinylidene chloride, tetrafluoroethylene, polycarbonate—polyorganosiloxane block copolymers, copolymers comprising aromatic ester, estercarbonate, and carbonate repeat units mixtures; and blends comprising at least one of the foregoing polymers. 
   
   
       5 . An article comprising the polymer of  claim 1 . 
   
   
       6 . An article, comprising a polycarbonate comprising structural units derived from a 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine, prepared in accordance with a method comprising heating a reaction mixture comprising:
 (i) a primary hydrocarbyl amine of Formula (II),
   R 1 NH 2   (II), 
   (ii) a phenolphthalein compound of Formula (III),   
     
       
         
         
             
             
         
       
     
     wherein R 1  is selected from a group consisting of a hydrogen and a hydrocarbyl group, R 2  is selected from the group consisting of a hydrogen, a hydrocarbyl group, and a halogen, and R 3  is selected from the group consisting of a hydrogen and a hydrocarbyl group; and forming said 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine, wherein the hydrocarbyl group is selected from the group consisting of an alkyl group, a cycloalkyl group, and an aryl group; forming an adduct of said 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine and said primary hydrocarbyl amine; precipitating said adduct; and decomposing said adduct to produce said 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine, wherein the method for producing the polycarbonate is selected from the group consisting of a melt transesterification polymerization method and an interfacial polymerization method. 
   
   
       7 . A 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine prepared in accordance with the method comprising heating a reaction mixture comprising:
 (i) a primary hydrocarbyl amine of Formula (II),
   R 1 NH 2   (II) 
   (ii) a phenolphthalein compound of Formula (III),   
     
       
         
         
             
             
         
       
     
     wherein R 1  is selected from a group consisting of a hydrogen and a hydrocarbyl group, R 2  is selected from the group consisting of a hydrogen, a hydrocarbyl group, and a halogen, and R 3  is selected from the group consisting of a hydrogen and a hydrocarbyl group; and forming said 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine, wherein the hydrocarbyl group is selected from the group consisting of an alkyl group, a cycloalkyl group, and an aryl group; forming an adduct of said 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine and said primary hydrocarbyl amine; precipitating said adduct; and decomposing said adduct to produce said 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine, wherein the 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine has a phenolphthalein content of less than or equal to 1,500 parts per million. 
   
   
       8 . A 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine prepared in accordance with the method comprising heating a reaction mixture comprising:
 (i) a primary hydrocarbyl amine of Formula (II),
   R 1 NH 2   (II) 
   (ii) a phenolphthalein compound of Formula (III),   
     
       
         
         
             
             
         
       
     
     wherein R 1  is selected from a group consisting of a hydrogen and a hydrocarbyl group, R 2  is selected from the group consisting of a hydrogen, a hydrocarbyl group, and a halogen, and R 3  is selected from the group consisting of a hydrogen and a hydrocarbyl group; and forming said 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine, wherein the hydrocarbyl group is selected from the group consisting of an alkyl group, a cycloalkyl group, and an aryl group; forming an adduct of said 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine and said primary hydrocarbyl amine; precipitating said adduct; and decomposing said adduct to produce said 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine, wherein the 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine has a purity of 99.5% to 99.9% as determined by high performance liquid chromatography.