Bisphenol polyether oligomers, methods of manufacture, and polycarbonates made therefrom

Abstract

A bisphenol polyether oligomer composition comprising greater than 90 wt. % of an oligomer of the formula wherein R a , R b , and R c are each independently a C 1-12 alkyl, C 1-12 alkoxy, or C 1-12 alkylarylene, each X a is independently a single bond, —O—, —S—, —S(O)—, —S(O) 2 —, —C(O)—, or a C 1-18 organic group, G is H or p, q, and t are each independently integers of 0 to 4, n is 1 to 10; and wherein the bisphenol polyether oligomer composition comprises: a total halide content of less than 1000 ppm, less than 1000 ppm of —CH 2 OH groups, less than 5 wt. % cyclic oligomers, and less than 100 ppm of a bisphenol of the formula wherein R a , R b , X a , p and q are the same as in the oligomer.

What is claimed is: 
     
         1 . A bisphenol polyether oligomer composition comprising greater than 90 wt. % of an oligomer of the formula 
       
         
           
           
               
               
           
         
       
       wherein
 R a , R b , and R c  are each independently a C 1-12  alkyl, C 1-12  alkoxy, or C 1-12  alkylarylene, 
 each X a  is independently a single bond, —O—, —S—, —S(O)—, —S(O) 2 —, —C(O)—, or a C 1-18  organic group, 
 G is H or 
 
       
         
           
           
               
               
           
         
         p, q, and t are each independently integers of 0 to 4, 
         n is 1 to 10; and 
       
       wherein the bisphenol polyether oligomer composition comprises:
 a total halide content of less than 1000 ppm, 
 less than 1000 ppm of —CH 2 OH groups, 
 less than 5 wt. % cyclic oligomers, and 
 less than 100 ppm of a bisphenol of the formula 
 
       
         
           
           
               
               
           
         
       
       wherein R a , R b , X a , p and q are the same as in the oligomer. 
     
     
         2 . The bisphenol polyether oligomer composition of  claim 1 , wherein the composition does not exhibit a half maximal inhibitory concentration (IC 50 ) less than 0.00025 M for alpha or beta in vitro estradiol receptors. 
     
     
         3 . The bisphenol polyether oligomer composition of  claim 1 , wherein the oligomer is of the formula 
       
         
           
           
               
               
           
         
       
       wherein G is H or 
       
         
           
           
               
               
           
         
       
       and the bisphenol is bisphenol A. 
     
     
         4 . The bisphenol polyether oligomer composition of  claim 1 , wherein the oligomer is a phthalimidine oligomer of the formula 
       
         
           
           
               
               
           
         
       
       wherein
 R a , R b , and R c  are each independently a C 1-12  alkyl, C 1-12  alkoxy, or C 1-12  alkylarylene, 
 R 3  is each independently a C 1-6  alkyl, 
 R 4  is hydrogen, C 1-6  alkyl, or a substituted or unsubstituted phenyl, 
 p, q, j, and t are each independently integers of 0 to 4, and 
 n is 1 to 10; and 
 
       wherein the bisphenol is of the formula 
       
         
           
           
               
               
           
         
       
       wherein R a , R b , R 3 , R 4 , p, q, and j are the same as defined for the phthalimidine oligomer. 
     
     
         5 . The bisphenol polyether oligomer composition of  claim 4 , wherein R 4  is methyl or phenyl, and p, q, j, and t are 0. 
     
     
         6 . The bisphenol polyether oligomer composition of  claim 1 , wherein the oligomer is a bisphenol A-phthalimidine polyether oligomer of the formula 
       
         
           
           
               
               
           
         
       
       wherein
 R a , R b , and R c  are each independently a C 1-12  alkyl, C 1-12  alkoxy, or C 1-12  alkylarylene, 
 R 3  is each independently a C 1-6  alkyl, 
 R 4  is hydrogen, C 1-6  alkyl, or a substituted or unsubstituted phenyl, 
 p, q, j, and t are each independently integers of 0 to 4, 
 α is 1 to 10 and β is 1 to 10, provided that α+β is 2 to 10, 
 G is H or 
 
       
         
           
           
               
               
           
         
       
       and
 A is 
 
       
         
           
           
               
               
           
         
       
       and 
       wherein the bisphenol is bisphenol A, a bisphenol of the formula (3b) 
       
         
           
           
               
               
           
         
       
       wherein R a , R b , R 3 , R 4 , p, q, and j are the same as defined for the bisphenol A-phthalimidine polyether oligomer, or a combination of bisphenol A and a bisphenol of formula (3b). 
     
     
         7 . A polyether polycarbonate comprising repeating carbonate unit of the formula 
       
         
           
           
               
               
           
         
       
       wherein
 R a , R b , and R c  are each independently a C 1-18  alkyl, C 1-18  alkoxy or alkylarylene, 
 each occurrence of X a  is independently single bond, —O—, —S—, —S(O)—, —S(O) 2 —, —C(O)—, or a C 1-18  organic group, 
 p, q, and t are each independently integers of 0 to 4; and 
 n is 1 to 10. 
 
     
     
         8 . The polyether polycarbonate of  claim 7 , comprising from 5 to 500 of polycarbonate repeat units. 
     
     
         9 . The polyether polycarbonate of  claim 7 , wherein each thermolytic and hydrolytic degradation product of each of the repeating carbonate units in the polycarbonate does not exhibit a half maximal inhibitory concentration (IC 50 ) less than 0.00025 M for alpha or beta in vitro estradiol receptors. 
     
     
         10 . The polyether polycarbonate of  claim 7 , wherein the polycarbonate has a glass transition temperature of greater than 135° C. 
     
     
         11 . The polyether polycarbonate of  claim 7 , wherein the endcap is a phenoxy group. 
     
     
         12 . The polyether polycarbonate of  claim 7 , further having
 an Mw of 3,000 to 80,000 Daltons,   a phenolic end group content less than 20 meq/kg,   a total chloride content less than 50 ppm,   a transition metal content less than 50 ppm, and   a residual phenolic monomer content less than 100 ppm.   
     
     
         13 . The polyether polycarbonate of  claim 7 , wherein the repeating carbonate units are of the formula 
       
         
           
           
               
               
           
         
         wherein n is 1 to 10; 
       
       
         
           
           
               
               
           
         
         wherein n is 1 to 10; 
       
       
         
           
           
               
               
           
         
         wherein n is 1 to 10; 
       
       
         
           
           
               
               
           
         
         wherein R 4  is phenyl or methyl and n is 1 to 10; 
       
       
         
           
           
               
               
           
         
         
           wherein a is 1 to 10 and β is 1 to 10, provided that α+β is 2 to 10, and A is 
         
       
       
         
           
           
               
               
           
         
         or a combination comprising at least one of the foregoing repeating carbonate units. 
       
     
     
         14 . The polyether polycarbonate of  claim 7 , wherein
 the polycarbonate is a poly(ester carbonate) further comprising repeating ester units derived from a dicarboxylic acid monomer, and   the dicarboxylic acid monomer does not exhibit a half maximal inhibitory concentration (IC 50 ) less than 0.00025 M for alpha or beta in vitro estradiol receptors.   
     
     
         15 . The polyether polycarbonate of  claim 14 , wherein the dicarboxylic acid monomer is a isophthalic acid, terephthalic acid, a C 6-36  aliphatic dicarboxylic acid, a hydroxy benzoic acid, or a combination comprising at least one of the foregoing. 
     
     
         16 . A polyether polycarbonate composition comprising the polyether polycarbonate of  claim 7 , and further comprising one or more additives, wherein each additive does not exhibit a half maximal inhibitory concentration (IC 50 ) less than 0.00025 M for alpha or beta in vitro estradiol receptors. 
     
     
         17 . The polyether polycarbonate of  claim 16 , wherein the additive is a stabilizer, antioxidant, colorant, impact modifier, flame retardant, anti-drip additive, mold release additive, lubricant, plasticizer, mineral, reinforcement additive, or a combination comprising at least one of the foregoing. 
     
     
         18 . The polyether polycarbonate of  claim 16 , wherein the additive is a phosphorus compound, wherein each hydrolysis product of the phosphorous compound does not exhibit a half maximal inhibitory concentration (IC 50 ) less than 0.00025 M for alpha or beta in vitro estradiol receptors. 
     
     
         19 . The polyether polycarbonate of  claim 16 , wherein the additive is a phosphite, wherein each hydrolysis product of the phosphite is does not exhibit a half maximal inhibitory concentration (IC 50 ) less than 0.00025 M for alpha or beta in vitro estradiol receptors. 
     
     
         20 . The polyether polycarbonate composition of  claim 16 , further comprising a second polymer component comprising a non-polyether polycarbonate polymer. 
     
     
         21 . The polymer composition of  claim 20 , wherein the second polymer component comprises a polycarbonate, polyester, polyolefin, polyetherimide, styrene-acrylonitrile, acrylonitrile-butadiene-styrene, methyl methacrylate, methyl methacrylate-butadiene-styrene, styrene-maleic anhydride, styrene-butadiene-styrene, styrene-ethylene-butylene-styrene, polystyrene, or a combination comprising at least one of the foregoing. 
     
     
         22 . An article comprising the polyether polycarbonate composition of  claim 16 . 
     
     
         23 . A method of manufacture of an article comprises molding, extruding, or shaping the polyether polycarbonate composition of  claim 16  into an article.