Polysulfone compositions and methods for the manufacture and use thereof
| Title: | Polysulfone compositions and methods for the manufacture and use thereof |
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| Patent Number: | 8,686,075 |
| Publication Date: | April 01, 2014 |
| Appl. No: | 13/564342 |
| Application Filed: | August 01, 2012 |
| Abstract: | This disclosure relates generally to polysulfone compositions whose residual phenolic monomers or phenolic degradation products exhibit little or no estradiol binding activity. Also disclosed are methods for making the disclosed polysulfones and articles of manufacture comprising the disclosed polysulfones. |
| Inventors: | Gallucci, Robert R. (Mt. Vernon, IN, US); Mahood, James A. (Evansville, IN, US); Odle, Roy R. (Mt. Vernon, IN, US); Dimond, Steve (Bedford, NH, US); Lutz, Eric Lee (Mt. Vernon, IN, US) |
| Assignees: | SABIC Innovative Plastics IP B.V. (Bergen op Zoom, NL) |
| Claim: | 1. A polysulfone composition comprising: a molecular weight in the range of from 10,000 to 120,000 Daltons; a phenolic end group content less than 20 meq/kg; a chloride content less than 20 ppm; a transition metal content less than 20 ppm; repeating units derived from reacting one or more phenolic monomers with a dihalo diaryl sulfone; 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 wherein when the polysulfone composition has more than zero to 1,000 ppm of one or more residual phenolic monomers or is subjected to conditions effective to provide one or more phenolic degradation products, each of the one or more residual phenolic monomers or phenolic degradation products does not exhibit a half maximal inhibitory concentration (IC 50) less than 0.00025M for alpha or beta in vitro estradiol receptors. |
| Claim: | 2. The polysulfone composition of claim 1 , wherein the one or more phenolic monomers comprises a bisphenolic monomer, a mono phenolic monomer, or a combination thereof. |
| Claim: | 3. The polysulfone composition of claim 1 , wherein the one or more phenolic monomers comprises resorcinol, hydroquinone, methyl hydroquinone, t-butyl hydroquinone, di-t-butyl hydroquinones, biphenols, tetramethyl bisphenol-A, Spiro biindane bisphenols, bis-(hydroxy aryl)-N-aryl isoindolinones, or any combination thereof. |
| Claim: | 4. A polysulfone composition comprising: repeating units derived from reacting one or more phenolic monomers with a dihalo diaryl sulfone; 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; wherein when the polysulfone composition has more than zero to 1,000 ppm of one or more residual phenolic monomers or is subjected to conditions effective to provide one or more phenolic degradation products, each of the one or more residual phenolic monomers or phenolic degradation products does not exhibit a half maximal inhibitory concentration (IC 50) less than 0.00025M for alpha or beta in vitro estradiol receptors; and wherein the polysulfone is end capped with phenol. |
| Claim: | 5. The polysulfone composition of claim 1 , wherein the polysulfone composition is a polyphenylene ether sulfone. |
| Claim: | 6. The polysulfone composition of claim 1 , wherein the polysulfone composition is a co-polysulfone composition comprising repeating subunits derived from a reaction of two or more phenolic monomers and the dihalo diaryl sulfone. |
| Claim: | 7. The polysulfone composition of claim 1 , further comprising one or more additives, 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. |
| Claim: | 8. The polysulfone composition of claim 7 , 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. |
| Claim: | 9. The polysulfone composition of claim 7 , wherein the one or more additives comprises a phosphite and wherein when the phosphite is subjected to conditions effective to provide one or more phosphite hydrolysis products, each of the one or more phosphite hydrolysis products does not exhibit a half maximal inhibitory concentration (IC 50) less than 0.00025M for alpha or beta in vitro estradiol receptors. |
| Claim: | 10. The polysulfone composition of claim 9 , wherein the phosphite comprises a diphenyl alkyl phosphite, phenyl dialkyl phosphite, trialkyl phosphite, dialkyl phosphite, triphenyl phosphite, diphenyl pentaerythritol diphosphite, or any combination thereof. |
| Claim: | 11. The polysulfone composition of claim 9 , wherein the phosphite has a molecular weight greater than 200 Daltons. |
| Claim: | 12. A polysulfone composition comprising: a molecular weight in the range of from 10,000 to 120,000 Daltons; a phenolic end group content less than 20 meq/kg; a chloride content less than 20 ppm; a transition metal content less than 20 ppm; a residual phenolic monomer content less than 100 ppm; repeating units derived from reacting one or more phenolic monomers with a dihalo diaryl sulfone; 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 wherein 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. |
| Claim: | 13. A polymer blend comprising: a) a first polymer component comprising at least one polysulfone composition according to claim 1 ; and b) a second polymer component comprising a polycarbonate, polyester carbonate, polyarylate, polyphenylene ether, polyamide, polyphenylene sulfide, polyester, styrene acrylonitrile, acrylonitrile butadiene styrene, methyl methacrylate, methacrylate butadiene styrene, styrene maleic anhydride, acrylic rubber, styrene butadiene styrene, styrene ethylene butadiene styrene, polystyrene, polyolefin, polyetherimide, polyetherimide sulfone, or any combination thereof. |
| Claim: | 14. An article of manufacture comprising a polysulfone composition according to claim 1 . |
| Claim: | 15. A method comprising: a) providing one or more phenolic monomers 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 dihalo diaryl sulfone; and c) reacting the one or more phenolic monomers and the dihalo diaryl sulfone under conditions effective to provide a polysulfone; wherein the polysulfone comprises: a molecular weight in the range of from 10,000 to 120,000 Daltons; a phenolic end group content less than 20 meq/kg; a chloride content less than 20 ppm; a transition metal content less than 20 ppm; and wherein when the polysulfone has more than zero to 1,000 ppm of one or more residual phenolic monomers or is subjected to conditions effective to provide one or more phenolic degradation products, each of the one or more residual phenolic monomers or phenolic degradation products does not exhibit a half maximal inhibitory concentration (IC 50) less than 0.00025M for alpha or beta in vitro estradiol receptors. |
| Claim: | 16. The method of claim 15 , wherein the one or more phenolic monomers comprises a bisphenolic monomer, a mono phenolic monomer, or a combination thereof. |
| Claim: | 17. The method of claim 15 , wherein the one or more phenolic monomers comprises resorcinol, hydroquinone, methyl hydroquinone, t-butyl hydroquinone, di-t-butyl hydroquinones, biphenols, tetramethyl bisphenol-A, spiro biindane bisphenols, bis-(hydroxy aryl)-N-aryl isoindolinones, or any combination thereof. |
| Claim: | 18. The method of claim 15 , wherein the dihalo diaryl sulfone comprises dichloro diphenyl sulfone. |
| Claim: | 19. The method of claim 15 , wherein the polysulfone is a polyphenylene ether sulfone. |
| Claim: | 20. The method of claim 15 , wherein the reaction conditions effective to provide a polysulfone comprise reacting the one or more phenolic monomers and dihalo diaryl sulfone in the presence of an end capping agent. |
| Claim: | 21. A method comprising: a) providing one or more phenolic monomers 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 dihalo diaryl sulfone; and c) reacting the one or more phenolic monomers and the dihalo diaryl sulfone under conditions effective to provide a polysulfone; wherein when the polysulfone has more than zero to 1,000 ppm of one or more residual phenolic monomers or is subjected to conditions effective to provide one or more phenolic degradation products, each of the one or more residual phenolic monomers or phenolic degradation products does not exhibit a half maximal inhibitory concentration (IC 50) less than 0.00025M for alpha or beta in vitro estradiol receptors; and wherein the polysulfone is end capped with phenol. |
| Claim: | 22. The method of claim 15 , wherein the polysulfone 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. |
| Claim: | 23. The method of claim 22 , 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. |
| Claim: | 24. The method of claim 22 , wherein the one or more additives comprises a phosphite and wherein when the phosphite is subjected to conditions effective to provide one or more phosphite hydrolysis products, each of the one or more phosphite hydrolysis products does not exhibit a half maximal inhibitory concentration (IC 50) less than 0.00025M for alpha or beta in vitro estradiol receptors. |
| Claim: | 25. The method of claim 24 , wherein the phosphite comprises a diphenyl alkyl phosphite, phenyl dialkyl phosphite, trialkyl phosphite, dialkyl phosphite, triphenyl phosphite, diphenyl pentaerythritol diphosphite, or any combination thereof. |
| Claim: | 26. The method of claim 24 , wherein the phosphite has a molecular weight greater than 200 Daltons. |
| Claim: | 27. The method of claim 15 , wherein the polysulfone is melt processed to provide the polysulfone in a pelletized form. |
| Claim: | 28. The method of claim 27 , wherein the pelletized polysulfone has a water content less than 100 ppm. |
| Claim: | 29. The polysulfone composition of claim 1 , wherein the dihalo diaryl sulfone comprises dichloro diphenyl sulfone. |
| Claim: | 30. The polysulfone composition of claim 1 , wherein the repeating units are derived from reacting the one or more phenolic monomers with the dihalo diaryl sulfone in the presence of an end capping agent. |
| Claim: | 31. The polysulfone composition of claim 1 , wherein the polysulfone is melt processed to provide the polysulfone in a pelletized form. |
| Claim: | 32. The polysulfone composition of claim 31 , wherein the pelletized polysulfone has a water content less than 100 ppm. |
| Claim: | 33. The polysulfone composition of claim 4 , wherein the one or more phenolic monomers comprises a bisphenolic monomer, a mono phenolic monomer, or a combination thereof. |
| Claim: | 34. The polysulfone composition of claim 4 , wherein the one or more phenolic monomers comprises resorcinol, hydroquinone, methyl hydroquinone, t-butyl hydroquinone, di-t-butyl hydroquinones, biphenols, tetramethyl bisphenol-A, spiro biindane bisphenols, bis-(hydroxy aryl)-N-aryl isoindolinones, or any combination thereof. |
| Claim: | 35. The polysulfone composition of claim 4 , wherein the polysulfone composition is a polyphenylene ether sulfone. |
| Claim: | 36. The polysulfone composition of claim 4 , wherein the polysulfone composition is a co-polysulfone composition comprising repeating subunits derived from a reaction of two or more phenolic monomers and the dihalo diaryl sulfone. |
| Claim: | 37. The polysulfone composition of claim 4 , further comprising one or more additives, 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. |
| Claim: | 38. The polysulfone composition of claim 37 , 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. |
| Claim: | 39. The polysulfone composition of claim 37 , wherein the one or more additives comprises a phosphite and wherein when the phosphite is subjected to conditions effective to provide one or more phosphite hydrolysis products, each of the one or more phosphite hydrolysis products does not exhibit a half maximal inhibitory concentration (IC 50) less than 0.00025M for alpha or beta in vitro estradiol receptors. |
| Claim: | 40. The polysulfone composition of claim 39 , wherein the phosphite comprises a diphenyl alkyl phosphite, phenyl dialkyl phosphite, trialkyl phosphite, dialkyl phosphite, triphenyl phosphite, diphenyl pentaerythritol diphosphite, or any combination thereof. |
| Claim: | 41. The polysulfone composition of claim 39 , wherein the phosphite has a molecular weight greater than 200 Daltons. |
| Claim: | 42. A polymer blend comprising: a) a first polymer component comprising at least one polysulfone composition according to claim 4 ; and b) a second polymer component comprising a polycarbonate, polyester carbonate, polyarylate, polyphenylene ether, polyamide, polyphenylene sulfide, polyester, styrene acrylonitrile, acrylonitrile butadiene styrene, methyl methacrylate, methacrylate butadiene styrene, styrene maleic anhydride, acrylic rubber, styrene butadiene styrene, styrene ethylene butadiene styrene, polystyrene, polyolefin, polyetherimide, polyetherimide sulfone, or any combination thereof. |
| Claim: | 43. An article of manufacture comprising a polysulfone composition according to claim 4 . |
| Claim: | 44. The polysulfone composition of claim 4 , wherein the dihalo diaryl sulfone comprises dichloro diphenyl sulfone. |
| Claim: | 45. The polysulfone composition of claim 4 , wherein the repeating units are derived from reacting the one or more phenolic monomers with the dihalo diaryl sulfone in the presence of an end capping agent. |
| Claim: | 46. The polysulfone composition of claim 4 , wherein the polysulfone is melt processed to provide the polysulfone in a pelletized form. |
| Claim: | 47. The polysulfone composition of claim 4 , wherein the pelletized polysulfone has a water content less than 100 ppm. |
| Claim: | 48. The polysulfone composition of claim 12 , wherein the one or more phenolic monomers comprises a bisphenolic monomer, a mono phenolic monomer, or a combination thereof. |
| Claim: | 49. The polysulfone composition of claim 12 , wherein the one or more phenolic monomers comprises resorcinol, hydroquinone, methyl hydroquinone, t-butyl hydroquinone, di-t-butyl hydroquinones, biphenols, tetramethyl bisphenol-A, spiro biindane bisphenols, bis-(hydroxy aryl)-N-aryl isoindolinones, or any combination thereof. |
| Claim: | 50. The polysulfone composition of claim 12 , wherein the polysulfone composition is a polyphenylene ether sulfone. |
| Claim: | 51. The polysulfone composition of claim 12 , wherein the polysulfone composition is a co-polysulfone composition comprising repeating subunits derived from a reaction of two or more phenolic monomers and the dihalo diaryl sulfone. |
| Claim: | 52. The polysulfone composition of claim 12 , further comprising one or more additives, 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. |
| Claim: | 53. The polysulfone composition of claim 52 , 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. |
| Claim: | 54. The polysulfone composition of claim 42 , wherein the one or more additives comprises a phosphite and wherein when the phosphite is subjected to conditions effective to provide one or more phosphite hydrolysis products, each of the one or more phosphite hydrolysis products does not exhibit a half maximal inhibitory concentration (IC 50) less than 0.00025M for alpha or beta in vitro estradiol receptors. |
| Claim: | 55. The polysulfone composition of claim 54 , wherein the phosphite comprises a diphenyl alkyl phosphite, phenyl dialkyl phosphite, trialkyl phosphite, dialkyl phosphite, triphenyl phosphite, diphenyl pentaerythritol diphosphite, or any combination thereof. |
| Claim: | 56. The polysulfone composition of claim 54 , wherein the phosphite has a molecular weight greater than 200 Daltons. |
| Claim: | 57. A polymer blend comprising: a) a first polymer component comprising at least one polysulfone composition according to claim 12 ; and b) a second polymer component comprising a polycarbonate, polyester carbonate, polyarylate, polyphenylene ether, polyamide, polyphenylene sulfide, polyester, styrene acrylonitrile, acrylonitrile butadiene styrene, methyl methacrylate, methacrylate butadiene styrene, styrene maleic anhydride, acrylic rubber, styrene butadiene styrene, styrene ethylene butadiene styrene, polystyrene, polyolefin, polyetherimide, polyetherimide sulfone, or any combination thereof. |
| Claim: | 58. An article of manufacture comprising a polysulfone composition according to claim 12 . |
| Claim: | 59. The polysulfone composition of claim 12 , wherein the dihalo diaryl sulfone comprises dichloro diphenyl sulfone. |
| Claim: | 60. The polysulfone composition of claim 12 , wherein the repeating units are derived from reacting the one or more phenolic monomers with the dihalo diaryl sulfone in the presence of an end capping agent. |
| Claim: | 61. The polysulfone composition of claim 12 , wherein the polysulfone is melt processed to provide the polysulfone in a pelletized form. |
| Claim: | 62. The polysulfone composition of claim 12 , wherein the pelletized polysulfone has a water content less than 100 ppm. |
| Claim: | 63. The method of claim 15 , wherein the polysulfone is a co-polysulfone comprising repeating subunits derived from a reaction of two or more phenolic monomers and the dihalo diaryl sulfone. |
| Claim: | 64. A polymer blend comprising: a) a first polymer component comprising at least one polysulfone made according to the method of claim 15 ; and b) a second polymer component comprising a polycarbonate, polyester carbonate, polyarylate, polyphenylene ether, polyamide, polyphenylene sulfide, polyester, styrene acrylonitrile, acrylonitrile butadiene styrene, methyl methacrylate, methacrylate butadiene styrene, styrene maleic anhydride, acrylic rubber, styrene butadiene styrene, styrene ethylene butadiene styrene, polystyrene, polyolefin, polyetherimide, polyetherimide sulfone, or any combination thereof. |
| Claim: | 65. An article of manufacture comprising a polysulfone made according to the method of claim 15 . |
| Claim: | 66. The method of claim 21 , wherein the one or more phenolic monomers comprises a bisphenolic monomer, a mono phenolic monomer, or a combination thereof. |
| Claim: | 67. The method of claim 21 , wherein the one or more phenolic monomers comprises resorcinol, hydroquinone, methyl hydroquinone, t-butyl hydroquinone, di-t-butyl hydroquinones, biphenols, tetramethyl bisphenol-A, Spiro biindane bisphenols, bis-(hydroxy aryl)-N-aryl isoindolinones, or any combination thereof. |
| Claim: | 68. The method of claim 21 , wherein the polysulfone composition is a polyphenylene ether sulfone. |
| Claim: | 69. The method of claim 21 , wherein the polysulfone composition is a co-polysulfone composition comprising repeating subunits derived from a reaction of two or more phenolic monomers and the dihalo diaryl sulfone. |
| Claim: | 70. The method of claim 21 , further comprising one or more additives, 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. |
| Claim: | 71. The method of claim 70 , 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. |
| Claim: | 72. The method of claim 70 , wherein the one or more additives comprises a phosphite and wherein when the phosphite is subjected to conditions effective to provide one or more phosphite hydrolysis products, each of the one or more phosphite hydrolysis products does not exhibit a half maximal inhibitory concentration (IC 50) less than 0.00025M for alpha or beta in vitro estradiol receptors. |
| Claim: | 73. The method of claim 72 , wherein the phosphite comprises a diphenyl alkyl phosphite, phenyl dialkyl phosphite, trialkyl phosphite, dialkyl phosphite, triphenyl phosphite, diphenyl pentaerythritol diphosphite, or any combination thereof. |
| Claim: | 74. The method of claim 72 , wherein the phosphite has a molecular weight greater than 200 Daltons. |
| Claim: | 75. A polymer blend comprising: a) a first polymer component comprising at least one polysulfone made according to the method of claim 21 ; and b) a second polymer component comprising a polycarbonate, polyester carbonate, polyarylate, polyphenylene ether, polyamide, polyphenylene sulfide, polyester, styrene acrylonitrile, acrylonitrile butadiene styrene, methyl methacrylate, methacrylate butadiene styrene, styrene maleic anhydride, acrylic rubber, styrene butadiene styrene, styrene ethylene butadiene styrene, polystyrene, polyolefin, polyetherimide, polyetherimide sulfone, or any combination thereof. |
| Claim: | 76. An article of manufacture comprising a polysulfone made according to the method of claim 21 . |
| Claim: | 77. The method of claim 21 , wherein the dihalo diaryl sulfone comprises dichloro diphenyl sulfone. |
| Claim: | 78. The method of claim 21 , wherein the reaction conditions effective to provide a polysulfone comprise reacting the one or more phenolic monomer and dihalo diaryl sulfone in the presence of an end capping agent. |
| Claim: | 79. The method of claim 21 , wherein the polysulfone is melt processed to provide the polysulfone in a pelletized form. |
| Claim: | 80. The method of claim 21 , wherein the pelletized polysulfone has a water content less than 100 ppm. |
| Current U.S. Class: | 524/147 |
| Patent References Cited: | 3634355 January 1972 Barr 4008203 February 1977 Jones 4108837 August 1978 Johnson et al. 4175175 November 1979 Johnson et al. 4503168 March 1985 Hartsing, Jr. 4689134 August 1987 Culkin et al. 6124399 September 2000 El-Hibri 7273919 September 2007 Steiger et al. 7393914 July 2008 Moore et al. 7705190 April 2010 Brunelle 7902316 March 2011 Johnson et al. 2007/0066738 March 2007 Gallucci et al. 2007/0292703 December 2007 Ikuta et al. |
| Primary Examiner: | Szekely, Peter |
| Attorney, Agent or Firm: | Ballard Spahr, LLP |
| Accession Number: | edspgr.08686075 |
| Database: | USPTO Patent Grants |
| Language: | English |
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