Polyester co-phosphonates

Abstract

Polyester co-polyphosphonates including of phosphonates covalently incorporated with polyesters and methods for making such polyester co-polyphosphonates are described herein. The polyester co-phosphonates and compositions prepared from these compounds exhibit an excellent combination of processing characteristics, mechanical and fire resistant properties.

1 .- 54 . (canceled) 
     
     
         55 . A random polyester co-phosphonate of Formula Ia, Ib, Ic, or combinations thereof: 
       
         
           
           
               
               
           
         
         wherein:
 each X is, independently, C 1-20  alkylene, C 2-20  alkenylene, C 2-20  alkynylene, C 5-20  cycloalkylene, or C 6-20  arylene; 
 each Z 1  is, independently, C 1-20  alkylene, C 2-20  alkenylene, C 2-20  alkynylene, C 5-20  cycloalkylene, or C 6-20  arylene; 
 each Ar is, independently, an aromatic group; 
 each n is, independently, an integer from 1 to about 100; 
 each m is, independently, an integer from 1 to about 20; and 
 each p is, independently, an integer from about 1 to about 100. 
 
       
     
     
         56 . The random polyester co-phosphonate of  claim 55 , wherein —O—Ar—O— is derived from a dihydroxy compound having one or more, optionally substituted aryl rings. 
     
     
         57 . The random polyester co-phosphonate of  claim 55 , wherein 
       
         
           
           
               
               
           
         
       
       is derived from a compound selected from the group consisting of adipic acid, terephthalic acid, isophthalic acid, naphthalene dicarboxylic acid, dimethyl terephthalate, dimethyl isophthalate, dimethyl naphthalate, and combinations thereof. 
     
     
         58 . The random polyester co-phosphonate of  claim 55 , wherein Z 1  is a C 1-20  alkylene. 
     
     
         59 . The random polyester co-phosphonate of  claim 55 , wherein —O—Ar—O— is derived from a bisphenol selected from the group consisting of resorcinol, hydroquinone, 4,4′-biphenol, 2,2-bis(4-hydroxyphenyl)propane, 3,3′-biphenol, 4,4′-dihydroxyphenyl ether, 4,4′dihydroxydiphenylsulfone, 9,9-dihydroxyphenyl fluorine, 1, I-bis(4-hydroxyphenyl)-3,3-dimethyl-5-methylcyclohexane, 4,4′-dihydroxybenzophenone, 4,4′-dihydroxyphenyl sulfide, 1-methyl-1-phenyl bis(4-hydroxyphenyl)methane, bis(3-hydroxyphenyl)methane, bis(4-hydroxyphenyl)methane, 9,9-bis(3-methyl-4-hydroxyphenyl)fluorene, 9,9-bis(3,5-dimethyl-4-hydroxyphenyl)fluorine, 1,4-bis[(4-hydroxyphenyl)-2-propyl]benzene, 1,4-bis[(4-hydroxyphenyl)-3,5 dimethylphenyl]-2-propyl]benzene, 4,4′-bis(4-hydroxyphenyl)diphenyl methane, 2,2-bis(4-hydroxyphenyl)hexafluoroisopropylidene, 1-trifluoromethyl-1-phenyl bis(4-hydroxyphenyl)methane, and combinations thereof. 
     
     
         60 . The random polyester co-phosphonate of  claim 55 , wherein X is naphthalene or phenyl, Z 1  is methylene, ethylene, propylene, butene, or pentene, and Ar is derived from resorcinol, hydroquinone, or bisphenol A. 
     
     
         61 . A random polyester co-phosphonate of Formula IV: 
       
         
           
           
               
               
           
         
         wherein:
 each X is, independently, C 1-20  alkylene, C 2-20  alkenylene, C 2-20  alkynylene, C 5-20  cycloalkylene, or C 6-20  arylene; 
 each Z 1  is, independently, C 1-20  alkylene, C 2-20  alkenylene, C 2-20  alkynylene, and C 5-20  cycloalkylene; 
 each Z 2  is, independently, C 1-20  alkylene, C 2-20  alkenylene, C 2-20  alkynylene, and C 5-20  cycloalkylene; 
 each n is, independently, an integer from 1 to about 100; and 
 each m is, independently, an integer from 1 to about 100. 
 
       
     
     
         62 . The random polyester co-phosphonate of  claim 61 , wherein 
       
         
           
           
               
               
           
         
       
       is derived from a compound selected from the group consisting of adipic acid, terephthalic acid, isophthalic acid, naphthalene dicarboxylic acid, dimethyl terephthalate, dimethyl isophthalate, dimethyl naphthalate, and combinations thereof. 
     
     
         63 . The random polyester co-phosphonate of  claim 61 , wherein Z 1  is a C 1-20  alkylene. 
     
     
         64 . The random polyester co-phosphonate of  claim 61 , wherein Z 2  is a C 1-20  alkylene. 
     
     
         65 . The random polyester co-phosphonate of  claim 61 , wherein X is naphthalene or phenyl and Z 1  and Z 2  are independently methylene, ethylene, propylene, butene, or pentene. 
     
     
         66 . A composition comprising at least one random polyester co-phosphonate selected from the group consisting of random polyester cophosphonates of Formula Ia, Ib, Ic, or combinations thereof: 
       
         
           
           
               
               
           
         
         wherein:
 each X is, independently, C 1-20  alkylene, C 2-20  alkenylene, C 2-20  alkynylene, C 5-20  cycloalkylene, or C 6-20  arylene; 
 each Z 1  is, independently, C 1-20  alkylene, C 2-20  alkenylene, C 2-20  alkynylene, C 5-2o  cycloalkylene, or C 6-20  arylene; 
 each Ar is, independently, an aromatic group; 
 each n is, independently, an integer from 1 to about 100; 
 each m is, independently, an integer from 1 to about 20; and 
 each p is, independently, an integer from about 1 to about 100; and 
 
         Formula IVa, IVb, or combinations thereof: 
       
       
         
           
           
               
               
           
         
         wherein:
 each X is, independently, C 1-20  alkylene, C 2-20  alkenylene, C 2-20  alkynylene, C 5-20  cycloalkylene, or C 6-20  arylene; 
 each Z 1  is, independently, C 1-20  alkylene, C 2-20  alkenylene, C 2-20  alkynylene, or C 5-20  cycloalkylene; 
 each Z 2  is, independently, C 1-20  alkylene, C 2-20  alkenylene, C 2-20  alkynylene, or C 5-2o  cycloalkylene; 
 each n is, independently, an integer from 1 to about 100; and 
 each m is, independently, an integer from 1 to about 100. 
 
       
     
     
         67 . The composition of  claim 66 , further comprising one or more additives selected from the group consisting of talc, silica, clays, chopped or continuous glass fiber, metal fibers, organic fibers, aramid fibers, carbon fibers, carbon nanofibers, ceramic fibers, surfactants, organic binders, polymeric binders, crosslinking agents, coupling agents, diluents, anti-dripping agents, fluorinated polyolefins, silicones, lubricants, mould release agents, pentaerythritol tetrastearate, nucleating agents, anti-static agents, conductive blacks, carbon black, graphite, graphene, graphene oxide, carbon nanotubes, carbon buckyballs, organic antistatics, polyalkylene ethers, alkylsulfonates, perfluoro sulfonic acid, perfluorbutane sulfonic acid potassium salt, polyamide-containing polymers, catalysts, colorants, inks, dyes, antioxidants, stabilizers, metal phosphinates, melamine cyanurate, melamine derivatives, flame retardants, or combinations thereof. 
     
     
         68 . The composition of  claim 66 , further comprising one or more engineering polymers. 
     
     
         69 . The composition of  claim 66 , further comprising one or more polymers selected from the group consisting of polycarbonates, epoxies derived polymers, polyepoxies, benzoxazines, polyacrylates, polyacrylonitriles, polyesters, poly(ethylene terephthalate), poly(trimethylene terephthalate), and poly(butylene terephthalate), unsaturated polyesters, polyamides, polystyrenes, polyureas, polyurethanes, polyphosphonates, polyphosphates, poly(acrylonitrile butadiene styrene)s, polyimides, polyarylates, poly(arylene ether)s, polyethylenes, polypropylenes, polyphenylene sulfides, poly(vinyl ester)s, polyvinyl chlorides, bismaleimide polymers, polyanhydrides, liquid crystalline polymers, and cellulose polymers. 
     
     
         70 . An article of manufacture comprising:
 at least one random polyester co-phosphonate selected from the group consisting of random polyester cophosphonates of Formula Ia, Ib, Ic, or combinations thereof:   
       
         
           
           
               
               
           
         
         wherein:
 each X is, independently, C 1-20  alkylene, C 2-20  alkenylene, C 2-20  alkynylene, C 5-20  cycloalkylene, or C 6-20  arylene; 
 each Z 1  is, independently, C 1-20  alkylene, C 2-20  alkenylene, C 2-20  alkynylene, C 5-20  cycloalkylene, or C 6-20  arylene; 
 each Ar is, independently, an aromatic group; 
 each n is, independently, an integer from 1 to about 100; 
 each m is, independently, an integer from 1 to about 20; and 
 each p is, independently, an integer from about 1 to about 100; and 
 
         Formula IVa, IVb, or combinations thereof: 
       
       
         
           
           
               
               
           
         
         wherein:
 each X is, independently, C 1-20  alkylene, C 2-20  alkenylene, C 2-20  alkynylene, C 5-20  cycloalkylene, or C 6-20  arylene; 
 each Z 1  is, independently, C 1-20  alkylene, C 2-20  alkenylene, C 2-20  alkynylene, or C 5-20  cycloalkylene; 
 each Z 2  is, independently, C 1-20  alkylene, C 2-20  alkenylene, C 2-20  alkynylene, or C 5-20  cycloalkylene; 
 each n is, independently, an integer from 1 to about 100; and 
 each m is, independently, an integer from 1 to about 100. 
 
       
     
     
         71 . The article of manufacture of  claim 70 , further comprising one or more additives selected from the group consisting of talc, silica, clays, chopped or continuous glass fiber, metal fibers, organic fibers, aramid fibers, carbon fibers, carbon nanofibers, ceramic fibers, surfactants, organic binders, polymeric binders, crosslinking agents, coupling agents, diluents, anti-dripping agents, fluorinated polyolefins, silicones, lubricants, mould release agents, pentaerythritol tetrastearate, nucleating agents, anti-static agents, conductive blacks, carbon black, graphite, graphene, graphene oxide, carbon nanotubes, carbon buckyballs, organic antistatics, polyalkylene ethers, alkylsulfonates, perfluoro sulfonic acid, perfluorbutane sulfonic acid potassium salt, polyamidecontaining polymers, catalysts, colorants, inks, dyes, antioxidants, stabilizers, metal phosphinates, melamine cyanurate, melamine derivatives, flame retardants, or combinations thereof. 
     
     
         72 . The article of manufacture of  claim 70 , further comprising one or more engineering polymers. 
     
     
         73 . The article of manufacture of  claim 70 , further comprising one or more polymers selected from the group consisting of polycarbonates, epoxies derived polymers, polyepoxies, benzoxazines, polyacrylates, polyacrylonitriles, polyesters, poly(ethylene terephthalate), poly(trimethylene terephthalate), and poly(butylene terephthalate), unsaturated polyesters, polyamides, polystyrenes, polyureas, polyurethanes, polyphosphonates, polyphosphates, poly(acrylonitrile butadiene styrene)s, polyimides, polyarylates, poly(arylene ether)s, polyethylenes, polypropylenes, polyphenylene sulfides, poly(vinyl ester)s, polyvinyl chlorides, bismaleimide polymers, polyanhydrides, liquid crystalline polymers, and cellulose polymers. 
     
     
         74 . The article of manufacture of  claim 70 , wherein the article is selected from the group consisting of injection molded articles, bottles, extruded sheets, films, tarpaulin, canoes, liquid crystal displays, holograms, filters, dielectric films, insulation for wires, insulating tapes, packaging materials, protective materials, films, and moldings. 
     
     
         75 . The article of manufacture of  claim 70 , wherein the article is selected from fibers, fabrics, yarns, woven and non-woven goods. 
     
     
         76 . The article of manufacture of  claim 70 , wherein the article is household furnishings. 
     
     
         77 . The article of manufacture of  claim 70 , wherein the article is selected from the group consisting of carpet, upholstery, fabrics, clothing, ropes, and belts.