Polyetherimide compositions and methods for the manufacture and use thereof

Abstract

This disclosure relates to polyetherimide compositions whose residual phenolic monomers exhibit little or no estradiol binding activity. Also disclosed are methods for making the disclosed polyetherimides and articles of manufacture comprising the disclosed polyetherimides.

1 . A polyetherimide composition, comprising:
 repeating units derived from one or more phenolic monomers, wherein each of the one or more phenolic monomers does not exhibit a half maximal inhibitory concentration (IC 50 ) less than 0.00025M for alpha or beta in vitro estradiol receptors, and   one or more residual phenolic monomers present at more than zero but less than or equal to 1,000 ppm   wherein when the residual phenolic monomer does not exhibit a half maximal inhibitory concentration (IC 50 ) less than 0.00025M for alpha or beta in vitro estradiol receptors.   
     
     
         2 . The polyetherimide composition of  claim 1 , wherein each of the one or more phenolic monomers does not exhibit a half maximal inhibitory concentration (IC 50 ) greater than or equal to 0.00025M for alpha or beta in vitro estradiol receptors. 
     
     
         3 . The polyetherimide composition of  claim 1 , wherein each of the one or more residual phenolic monomers does not exhibit a half maximal inhibitory concentration (IC 50 ) greater than or equal to 0.00025M for alpha or beta in vitro estradiol receptors. 
     
     
         4 . The polyetherimide composition of  claim 4 , wherein the phenolic monomer comprises a bisphenolic monomer, a mono phenolic monomer, or a combination thereof. 
     
     
         5 . The polyetherimide composition of  claim 1 , wherein the one or more phenolic monomer comprises resorcinol, hydroquinone, methyl hydroquinone, t-butyl hydroquinone, di-t-butyl hydroquinones (DTBHQ), biphenols, tetramethyl bisphenol-A, spiro biindane bisphenols (SBIBP), bis-(hydroxy aryl)-N-aryl isoindolinones or any combination thereof. 
     
     
         6 . The polyetherimide composition of  claim 1 , wherein the polyetherimide is end capped with phenol. 
     
     
         7 . The polyetherimide composition of  claim 1 , wherein the polyetherimide is a co-polyetherimide comprising repeating units derived from two or more phenolic monomers. 
     
     
         8 . The polyetherimide composition of  claim 1 , further comprising one or more additives and wherein each of the one or more additives does not exhibit a half maximal inhibitory concentration (IC 50 ) less than 0.00025M for alpha or beta in vitro estradiol receptors. 
     
     
         9 . The polyetherimide composition of  claim 8 , wherein the one or more additive comprises a stabilizer, antioxidant, colorant, impact modifier, flame retardant, anti drip additive, mold release additive, lubricant, plasticizer, mineral, reinforcement additive, or any combination thereof. 
     
     
         10 . The polyetherimide composition of  claim 8 , wherein the one or more additive comprises a phosphite and wherein when the phosphite, phosphonate or mixture thereof is subjected to conditions effective to provide one or more phosphite, or phosphonate hydrolysis product, each of the one or more phosphite or phosphonate hydrolysis products does not exhibit a half maximal inhibitory concentration (IC 50 ) less than 0.00025M for alpha or beta in vitro estradiol receptors. 
     
     
         11 . The polyetherimide composition of  claim 10 , wherein the phosphite comprises a diphenyl alkyl phosphite, phenyl dialkyl phosphite, trialkyl phosphite, dialkyl phosphite, triphenyl phosphite, diphenyl pentaerythritol diphosphite, or any combination thereof. 
     
     
         12 . The polyetherimide composition of  claim 11 , wherein the phosphite has a Mw greater than 200 Daltons. 
     
     
         13 . The polyetherimide composition of  claim 1 , further comprising:
 a) a Mw in the range of from 3,000 to 80,000 Daltons;   b) a phenolic end group content less than 20 meq/kg;   c) a chloride content less than 1000 ppm; and   d) a transition metal content less than 20 ppm.   e) a residual phenolic monomer at less than 100 ppm   
     
     
         14 . The polyetherimide composition of  claim 13  wherein the residual solvent content is less than 100 ppm. 
     
     
         15 . The polyetherimide composition of  claim 1  having a Tg from 200 to 320° C., a weight gain on immersion in water for 24 hrs at 23° C. of less than 3.5% and a coefficient of expansion from 30 to 50 ppm/° C. 
     
     
         16 . A polymer blend comprising:
 a) a first polymer component comprising at least one polyetherimide composition according to  claim 1 ; and   b) a second polymer component comprising a polycarbonate, polyester carbonate, polyarylate, polyphenylene ether, polyamide, polyphenylene sulfide, polyester, polysulfones, polyethersulfones, polyphenylene ether sulfones, polyolefin, or any combination thereof.   
     
     
         17 . An article of manufacture comprising a polyetherimide composition according to  claim 1 . 
     
     
         18 . A method for the manufacture of a polyetherimide, comprising:
 a) providing a phenolic monomer that does not exhibit a half maximal inhibitory concentration (IC 50 ) less than 0.00025M for alpha or beta in vitro estradiol receptors;   b) providing a bis phthalimide; and   c) reacting the phenolic monomer and the bis phthalimide under conditions effective to provide a polyetherimide comprising a residual phenolic monomer content of more than zero and less than 1,000 ppm,
 wherein the polyetherimide provided in step c) is further characterized in that the residual phenolic monomer does not exhibit a half maximal inhibitory concentration (IC 50 ) less than 0.00025M for alpha or beta in vitro estradiol receptors. 
   
     
     
         19 . The method of  claim 18 , wherein the phenolic monomer comprises a bisphenolic monomer, a mono phenolic monomer, or a combination thereof. 
     
     
         20 . The method of  claim 18 , wherein the one or more phenolic monomer comprises resorcinol, hydroquinone, methyl hydroquinone, t-butyl hydroquinone, di-t-butyl hydroquinones (DTBHQ), biphenols, tetramethyl bisphenol-A, spiro biindane bisphenols (SBIBP), bis-(hydroxy aryl)-N-aryl isoindolinones or any combination thereof. 
     
     
         21 . The method of  claim 18 , wherein the bis phthalimide is a bis halo phthalimide. 
     
     
         22 . The method of  claim 18 , further comprising the presence of 0.1 to 10 wt % of a phase transfer catalyst during the polymerization step c. 
     
     
         23 . The method of  claim 18 , wherein the reaction conditions effective to provide a polyetherimide comprise reacting the phenolic monomer and the phthalimide in the presence of an end capping agent. 
     
     
         24 . The method of  claim 23 , wherein the end capping agent comprises phenol. 
     
     
         25 . The method of  claim 18 , wherein after step c) the polyetherimide is compounded with one or more additives and wherein each of the one or more additives does not exhibit a half maximal inhibitory concentration (IC 50 ) less than 0.00025M for alpha or beta in vitro estradiol receptors. 
     
     
         26 . The method of  claim 25 , wherein the one or more additives comprises a stabilizer, antioxidant, colorant, impact modifier, flame retardant, anti drip additive, mold release additive, lubricant, plasticizer, mineral, reinforcement additive, or any combination thereof. 
     
     
         27 . The method of  claim 25 , wherein the one or more additives comprises a phosphite, phosphonate or mixture thereof and wherein when the phosphite, phosphonate or mixture thereof, is subjected to conditions effective to provide one or more phosphite or phosphonate hydrolysis product, each of the one or more phosphite or phosphonate products does not exhibit a half maximal inhibitory concentration (IC 50 ) less than 0.00025M for alpha or beta in vitro estradiol receptors. 
     
     
         28 . The method of  claim 27 , wherein the phosphite comprises a diphenyl alkyl phosphite, phenyl dialkyl phosphite, trialkyl phosphite, dialkyl phosphite, triphenyl phosphite, diphenyl pentaerythritol diphosphite, or any combination thereof. 
     
     
         29 . The method of  claim 28 , wherein the phosphite has a Mw greater than 200 Daltons. 
     
     
         30 . The method of  claim 18 , wherein the polyetherimide of step c) is melt processed to provide the polyetherimide in a pelletized form. 
     
     
         31 . The method of  claim 30 , wherein the pelletized polyetherimide is dried to provide a pelletized polyetherimide having a water content less than 100 ppm. 
     
     
         32 . A method for the manufacture of a polyetherimide, comprising:
 a) providing an aromatic bis(ether anhydride) derived from a phenolic monomer that does not exhibit a half maximal inhibitory concentration (IC 50 ) less than 0.00025M for alpha or beta in vitro estradiol receptors;   b) providing a diamine; and   c) reacting the aromatic bis(ether anhydride) the diamine under conditions effective to provide a polyetherimide comprising a residual phenolic monomer content less or more than zero and less than 1,000 ppm,
 wherein the polyetherimide provided in step c) is further characterized in that the residual phenolic monomer does not exhibit a half maximal inhibitory concentration (IC 50 ) less than 0.00025M for alpha or beta in vitro estradiol receptors. 
   
     
     
         33 . The method of  claim 32 , wherein the phenolic monomer comprises a bisphenolic monomer, a mono phenolic monomer, or a combination thereof. 
     
     
         34 . The method of  claim 32 , wherein the one or more phenolic monomer comprises resorcinol, hydroquinone, methyl hydroquinone, t-butyl hydroquinone, di-t-butyl hydroquinones (DTBHQ), biphenols, tetramethyl bisphenol-A, spiro biindane bisphenols (SBIBP), bis-(hydroxy aryl)-N-aryl isoindolinones or any combination thereof. 
     
     
         35 . The method of  claim 32 , wherein the diamine comprises m-phenylene diamine, p-phenylene diamine, diamino diphenyl sulfone, or a combination thereof. 
     
     
         36 . The method of  claim 32 , wherein after step c) the polyetherimide is compounded with one or more additive and wherein each of the one or more additives does not exhibit a half maximal inhibitory concentration (IC 50 ) less than 0.00025M for alpha or beta in vitro estradiol receptors. 
     
     
         37 . The method of  claim 36 , wherein the one or more additive comprises a stabilizer, antioxidant, colorant, impact modifier, flame retardant, anti drip additive, mold release additive, lubricant, plasticizer, mineral, reinforcement additive, or any combination thereof. 
     
     
         38 . The method of  claim 36 , wherein the one or more additive comprises a phosphite, phosphonate or mixture thereof and wherein when the phosphite, phosphonate or mixture thereof, is subjected to conditions effective to provide one or more phosphite or phosphonate hydrolysis product, each of the one or more hydrolysis products does not exhibit a half maximal inhibitory concentration (IC 50 ) less than 0.00025M for alpha or beta in vitro estradiol receptors. 
     
     
         39 . The method of  claim 38 , wherein the phosphite comprises a diphenyl alkyl phosphite, phenyl dialkyl phosphite, trialkyl phosphite, dialkyl phosphite, triphenyl phosphite, diphenyl pentaerythritol diphosphite, or any combination thereof. 
     
     
         40 . The method of  claim 39 , wherein the phosphite has a Mw greater than 200 Daltons. 
     
     
         41 . The method of  claim 32 , wherein the polyetherimide of step c) is melt processed to provide the polyetherimide in a pelletized form. 
     
     
         42 . The method of  claim 41 , wherein the pelletized polyetherimide is dried to provide a pelletized polyetherimide having a water content less than 100 ppm. 
     
     
         43 . The method of  claim 32  wherein the polyetherimide has a Tg from 200 to 320° C., a weight gain on immersion in water for 24 hrs at 23° C. of less than 3.5% and a coefficient of expansion from 30 to 50 ppm/° C.