AU2012260780B2 - Polymers with reduced estrogenic activity - Google Patents
Polymers with reduced estrogenic activity Download PDFInfo
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- AU2012260780B2 AU2012260780B2 AU2012260780A AU2012260780A AU2012260780B2 AU 2012260780 B2 AU2012260780 B2 AU 2012260780B2 AU 2012260780 A AU2012260780 A AU 2012260780A AU 2012260780 A AU2012260780 A AU 2012260780A AU 2012260780 B2 AU2012260780 B2 AU 2012260780B2
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- Prior art keywords
- polymer
- membrane
- group
- aromatic
- present
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 229920000642 polymer Polymers 0.000 title claims abstract description 141
- 230000001076 estrogenic effect Effects 0.000 title description 7
- 230000002829 reductive effect Effects 0.000 title description 6
- -1 aromatic diol Chemical class 0.000 claims description 85
- 238000000034 method Methods 0.000 claims description 59
- 239000012528 membrane Substances 0.000 claims description 40
- 229920000110 poly(aryl ether sulfone) Polymers 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 229920000515 polycarbonate Polymers 0.000 claims description 11
- 239000004417 polycarbonate Substances 0.000 claims description 11
- 238000000926 separation method Methods 0.000 claims description 9
- 235000013305 food Nutrition 0.000 claims description 8
- 239000004615 ingredient Substances 0.000 claims description 8
- 239000008280 blood Substances 0.000 claims description 7
- 210000004369 blood Anatomy 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 239000002351 wastewater Substances 0.000 claims description 4
- 235000013361 beverage Nutrition 0.000 claims description 3
- 238000005266 casting Methods 0.000 claims description 3
- 239000012510 hollow fiber Substances 0.000 claims description 3
- 238000009987 spinning Methods 0.000 claims description 3
- 239000002131 composite material Substances 0.000 claims description 2
- 238000001631 haemodialysis Methods 0.000 claims description 2
- 230000000322 hemodialysis Effects 0.000 claims description 2
- 238000012545 processing Methods 0.000 claims description 2
- 239000008213 purified water Substances 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- 239000000178 monomer Substances 0.000 abstract description 87
- 125000003118 aryl group Chemical group 0.000 description 69
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000000460 chlorine Substances 0.000 description 25
- 239000002904 solvent Substances 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 19
- 125000000217 alkyl group Chemical group 0.000 description 19
- GPAPPPVRLPGFEQ-UHFFFAOYSA-N 4,4'-dichlorodiphenyl sulfone Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 GPAPPPVRLPGFEQ-UHFFFAOYSA-N 0.000 description 17
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 17
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- 102100038595 Estrogen receptor Human genes 0.000 description 16
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 16
- 229910052736 halogen Inorganic materials 0.000 description 16
- 150000002367 halogens Chemical class 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 15
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 15
- 230000004044 response Effects 0.000 description 15
- 229910052801 chlorine Inorganic materials 0.000 description 14
- 238000006068 polycondensation reaction Methods 0.000 description 14
- IBRQUKZZBXZOBA-UHFFFAOYSA-N 1-chloro-3-(3-chlorophenyl)sulfonylbenzene Chemical compound ClC1=CC=CC(S(=O)(=O)C=2C=C(Cl)C=CC=2)=C1 IBRQUKZZBXZOBA-UHFFFAOYSA-N 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000003513 alkali Substances 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 12
- 238000005227 gel permeation chromatography Methods 0.000 description 12
- 125000005843 halogen group Chemical group 0.000 description 12
- 238000002957 GeneBLAzer Methods 0.000 description 11
- 108010038795 estrogen receptors Proteins 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 150000003457 sulfones Chemical class 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 10
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 150000001408 amides Chemical class 0.000 description 9
- 238000003556 assay Methods 0.000 description 9
- 238000005516 engineering process Methods 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 150000003949 imides Chemical class 0.000 description 9
- 239000003880 polar aprotic solvent Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 150000003568 thioethers Chemical class 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 108090000204 Dipeptidase 1 Proteins 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 102000006635 beta-lactamase Human genes 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000470 constituent Substances 0.000 description 8
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 8
- 230000007547 defect Effects 0.000 description 8
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical group C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 8
- 229920002492 poly(sulfone) Polymers 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 238000012546 transfer Methods 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 7
- 150000008041 alkali metal carbonates Chemical class 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000005600 alkyl phosphonate group Chemical group 0.000 description 6
- 150000008052 alkyl sulfonates Chemical class 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 6
- 230000027455 binding Effects 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 6
- 229940050176 methyl chloride Drugs 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 5
- 238000005345 coagulation Methods 0.000 description 5
- 230000015271 coagulation Effects 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 102000006255 nuclear receptors Human genes 0.000 description 5
- 108020004017 nuclear receptors Proteins 0.000 description 5
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 125000001453 quaternary ammonium group Chemical group 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- PLVUIVUKKJTSDM-UHFFFAOYSA-N 1-fluoro-4-(4-fluorophenyl)sulfonylbenzene Chemical compound C1=CC(F)=CC=C1S(=O)(=O)C1=CC=C(F)C=C1 PLVUIVUKKJTSDM-UHFFFAOYSA-N 0.000 description 4
- GIXXQTYGFOHYPT-UHFFFAOYSA-N Bisphenol P Chemical compound C=1C=C(C(C)(C)C=2C=CC(O)=CC=2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 GIXXQTYGFOHYPT-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- 229910004013 NO 2 Inorganic materials 0.000 description 4
- 108020005497 Nuclear hormone receptor Proteins 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 4
- 229960000956 coumarin Drugs 0.000 description 4
- 235000001671 coumarin Nutrition 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 108020001756 ligand binding domains Proteins 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 4
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 3
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical group OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
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- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
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- 238000004821 distillation Methods 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
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- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical group O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 3
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- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- 239000000556 agonist Substances 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
- C08G79/04—Phosphorus linked to oxygen or to oxygen and carbon
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- B01D71/66—Polymers having sulfur in the main chain, with or without nitrogen, oxygen or carbon only
- B01D71/68—Polysulfones; Polyethersulfones
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/20—Polysulfones
- C08G75/23—Polyethersulfones
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- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
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- Y10T428/2913—Rod, strand, filament or fiber
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Landscapes
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- Health & Medical Sciences (AREA)
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- Polyethers (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Polyurethanes Or Polyureas (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161489955P | 2011-05-25 | 2011-05-25 | |
| US61/489,955 | 2011-05-25 | ||
| US201161494567P | 2011-06-08 | 2011-06-08 | |
| US61/494,567 | 2011-06-08 | ||
| EP11182062.7 | 2011-09-20 | ||
| EP11182062 | 2011-09-20 | ||
| PCT/EP2012/059775 WO2012160172A1 (en) | 2011-05-25 | 2012-05-24 | Polymers with reduced estrogenic activity |
Publications (2)
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| AU2012260780A1 AU2012260780A1 (en) | 2013-11-28 |
| AU2012260780B2 true AU2012260780B2 (en) | 2015-12-17 |
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|---|---|---|---|
| AU2012260780A Ceased AU2012260780B2 (en) | 2011-05-25 | 2012-05-24 | Polymers with reduced estrogenic activity |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20140113093A1 (enExample) |
| EP (1) | EP2714772A1 (enExample) |
| JP (1) | JP5993941B2 (enExample) |
| KR (1) | KR101912484B1 (enExample) |
| CN (1) | CN103781822B (enExample) |
| AU (1) | AU2012260780B2 (enExample) |
| BR (1) | BR112013030102A2 (enExample) |
| SG (1) | SG194798A1 (enExample) |
| WO (1) | WO2012160172A1 (enExample) |
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|---|---|---|---|---|
| KR20130061132A (ko) | 2010-04-16 | 2013-06-10 | 발스파 소싱 인코포레이티드 | 패키징 용품을 위한 코팅 조성물 및 코팅 방법 |
| CN107434926B (zh) | 2011-02-07 | 2021-04-06 | 宣伟投资管理有限公司 | 容器和其它制品用涂料组合物和涂布方法 |
| US8686075B2 (en) * | 2011-08-22 | 2014-04-01 | Sabic Innovative Plastics Ip B.V. | Polysulfone compositions and methods for the manufacture and use thereof |
| CN104582671B (zh) | 2012-08-09 | 2018-06-29 | 威士伯采购公司 | 牙科材料和制备方法 |
| EP2882818B1 (en) | 2012-08-09 | 2020-05-06 | Swimc Llc | Stabilizer and coating compositions thereof |
| WO2014025997A1 (en) | 2012-08-09 | 2014-02-13 | Valspar Sourcing, Inc. | Compositions for containers and other articles and methods of using same |
| WO2014025400A1 (en) | 2012-08-09 | 2014-02-13 | Valspar Sourcing, Inc. | Developer for thermally responsive record materials |
| CN104540874B (zh) | 2012-08-09 | 2018-05-01 | 威士伯采购公司 | 聚碳酸酯 |
| US10526502B2 (en) | 2012-08-09 | 2020-01-07 | Swimc Llc | Container coating system |
| KR102368334B1 (ko) * | 2013-09-09 | 2022-03-02 | 바스프 에스이 | 막 적용을 위한 폴리아릴렌 에테르 술폰 폴리머 |
| US20150183929A1 (en) | 2013-12-30 | 2015-07-02 | Sabic Innovative Plastics Ip B.V | Bisphenol polyether oligomers, methods of manufacture, and polycarbonates made therefrom |
| CN106536624B (zh) | 2014-04-14 | 2019-11-19 | 宣伟投资管理有限公司 | 制备用于容器和其它制品的组合物的方法以及使用所述组合物的方法 |
| JP6379995B2 (ja) * | 2014-10-24 | 2018-08-29 | Nok株式会社 | 炭素膜用製膜原液およびこれを用いた中空糸炭素膜の製造方法 |
| TWI614275B (zh) | 2015-11-03 | 2018-02-11 | Valspar Sourcing Inc | 用於製備聚合物的液體環氧樹脂組合物 |
| US20230001362A1 (en) | 2019-12-05 | 2023-01-05 | Solvay Specialty Polymers Usa, Llc | Process for preparing a poly(aryl ether sulfone) (paes) polymer |
| KR20230119135A (ko) | 2020-12-18 | 2023-08-16 | 솔베이 스페셜티 폴리머즈 유에스에이, 엘.엘.씨. | Bpa 및 bps가 없는 바이오-기반 설폰 공중합체 |
| WO2023139133A1 (en) | 2022-01-19 | 2023-07-27 | Solvay Specialty Polymers Usa, Llc | Shaped article comprising a poly(aryl ether sulfone) (paes) polymer and method of making using melt processing |
| WO2025210172A1 (en) | 2024-04-05 | 2025-10-09 | Syensqo Specialty Polymers Usa, Llc | Polyarylethersulfone containing phosphorous and made from dihaloarylsulfone and alicyclic diol |
| WO2025210173A1 (en) | 2024-04-05 | 2025-10-09 | Syensqo Specialty Polymers Usa, Llc | Polyarylethersulfone containing phosphorous and made from dihaloarylsulfone and acyclic diol |
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| DE1619478C3 (de) * | 1966-06-03 | 1974-11-07 | Bayer Ag, 5090 Leverkusen | Verfahren zum Färben und Bedrucken von Fasersubstraten |
| BE699272A (enExample) * | 1966-06-04 | 1967-11-30 | ||
| US4156068A (en) * | 1976-01-21 | 1979-05-22 | Ici Americas Inc. | High molecular weight polyethersulfones |
| JPS5995905A (ja) * | 1982-11-22 | 1984-06-02 | Daicel Chem Ind Ltd | ポリスルホン樹脂半透膜の製造方法 |
| JPS5995904A (ja) * | 1982-11-24 | 1984-06-02 | Daicel Chem Ind Ltd | ポリスルホン樹脂半透膜の製法 |
| DE3342433A1 (de) * | 1983-11-24 | 1985-06-05 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von aromatischen polyaethern |
| CA1250693A (en) * | 1985-02-13 | 1989-02-28 | Amoco Corporation | Polyaryl ether sulphone polymers |
| JP2618650B2 (ja) * | 1987-09-11 | 1997-06-11 | 株式会社リコー | 感熱記録材料 |
| DE3823306A1 (de) * | 1988-07-09 | 1990-01-18 | Bayer Ag | Verwendung von homopolycarbonaten aus 3,3'-dihydroxydiphenylether zur modifizierung von folien aus thermoplasten |
| US4873371A (en) * | 1988-08-01 | 1989-10-10 | General Electric Company | Hydroxy-terminated arylene ethers, and method for making |
| JPH05329345A (ja) * | 1992-06-01 | 1993-12-14 | Nitto Denko Corp | ポリスルホン系膜及び逆浸透複合膜 |
| DE60027252T2 (de) * | 1999-11-02 | 2007-01-04 | Mitsubishi Gas Chemical Co., Inc. | Polycarbonatharz |
| US6576735B2 (en) * | 1999-11-02 | 2003-06-10 | Mitsubishi Gas Chemical Company, Inc. | Polycarbonate resin |
| DE10007272B4 (de) * | 2000-02-17 | 2005-04-07 | Membrana Gmbh | Blockcopolymere mit sulfonierten Polyethersulfoneinheiten |
| CA2402841C (en) * | 2000-03-22 | 2009-11-24 | Victrex Manufacturing Limited | Ion exchange materials |
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| US7229580B2 (en) * | 2003-05-05 | 2007-06-12 | Porogen Corporation | Preparation of porous poly(aryl ether) articles and use thereof |
| US8211576B2 (en) * | 2003-09-30 | 2012-07-03 | Sumitomo Chemical Company, Limited | Block copolymers and use thereof |
| CN1989174A (zh) * | 2004-07-22 | 2007-06-27 | 索维高级聚合物股份有限公司 | 聚砜聚醚嵌段共聚物，合成其的方法和由其制造的膜 |
| EP1524297A1 (en) * | 2004-12-22 | 2005-04-20 | Solvay Advanced Polymers, L.L.C. | Sulfone polymer composition |
| US20080143014A1 (en) * | 2006-12-18 | 2008-06-19 | Man-Wing Tang | Asymmetric Gas Separation Membranes with Superior Capabilities for Gas Separation |
| JP2010058096A (ja) * | 2008-09-08 | 2010-03-18 | Toray Ind Inc | 親水化ポリエーテルスルホン分離膜及びその製造方法 |
| EP2253367B1 (en) * | 2009-05-20 | 2014-11-19 | Gambro Lundia AB | Membranes having improved performance |
| US9018335B2 (en) * | 2010-12-29 | 2015-04-28 | Empire Technology Development Llc | Substances for use as bisphenol a substitutes |
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2012
- 2012-05-24 AU AU2012260780A patent/AU2012260780B2/en not_active Ceased
- 2012-05-24 JP JP2014511889A patent/JP5993941B2/ja not_active Expired - Fee Related
- 2012-05-24 KR KR1020137034276A patent/KR101912484B1/ko not_active Expired - Fee Related
- 2012-05-24 WO PCT/EP2012/059775 patent/WO2012160172A1/en not_active Ceased
- 2012-05-24 CN CN201280035491.2A patent/CN103781822B/zh not_active Expired - Fee Related
- 2012-05-24 EP EP12723207.2A patent/EP2714772A1/en not_active Withdrawn
- 2012-05-24 US US14/119,467 patent/US20140113093A1/en not_active Abandoned
- 2012-05-24 BR BR112013030102A patent/BR112013030102A2/pt not_active IP Right Cessation
- 2012-05-24 SG SG2013081955A patent/SG194798A1/en unknown
-
2013
- 2013-11-20 ZA ZA2013/08712A patent/ZA201308712B/en unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| SG194798A1 (en) | 2013-12-30 |
| KR101912484B1 (ko) | 2018-10-26 |
| EP2714772A1 (en) | 2014-04-09 |
| BR112013030102A2 (pt) | 2016-09-20 |
| US20140113093A1 (en) | 2014-04-24 |
| AU2012260780A1 (en) | 2013-11-28 |
| JP5993941B2 (ja) | 2016-09-21 |
| CN103781822A (zh) | 2014-05-07 |
| ZA201308712B (en) | 2015-06-24 |
| WO2012160172A1 (en) | 2012-11-29 |
| CN103781822B (zh) | 2016-08-17 |
| JP2014517863A (ja) | 2014-07-24 |
| KR20140034254A (ko) | 2014-03-19 |
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