JP2022500525A - ポリアリーレンエーテル - Google Patents
ポリアリーレンエーテル Download PDFInfo
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- JP2022500525A JP2022500525A JP2021513831A JP2021513831A JP2022500525A JP 2022500525 A JP2022500525 A JP 2022500525A JP 2021513831 A JP2021513831 A JP 2021513831A JP 2021513831 A JP2021513831 A JP 2021513831A JP 2022500525 A JP2022500525 A JP 2022500525A
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- JP
- Japan
- Prior art keywords
- polyarylene ether
- compound
- mol
- mixture
- polyarylene
- 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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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims abstract description 253
- 229920000412 polyarylene Polymers 0.000 title claims abstract description 170
- 150000001875 compounds Chemical class 0.000 claims abstract description 88
- 239000000203 mixture Substances 0.000 claims abstract description 72
- -1 ether sulfone Chemical class 0.000 claims abstract description 69
- 238000000034 method Methods 0.000 claims abstract description 65
- 238000004519 manufacturing process Methods 0.000 claims abstract description 51
- KLDXJTOLSGUMSJ-UNTFVMJOSA-N (3s,3ar,6s,6ar)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol Chemical compound O[C@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-UNTFVMJOSA-N 0.000 claims abstract description 23
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 claims abstract description 22
- 229960002479 isosorbide Drugs 0.000 claims abstract description 22
- 239000000835 fiber Substances 0.000 claims abstract description 18
- 239000010408 film Substances 0.000 claims abstract description 11
- 238000000576 coating method Methods 0.000 claims abstract description 10
- 239000006260 foam Substances 0.000 claims abstract description 6
- 239000012528 membrane Substances 0.000 claims description 65
- 150000002009 diols Chemical class 0.000 claims description 34
- 150000003457 sulfones Chemical class 0.000 claims description 17
- 150000002576 ketones Chemical class 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 230000001588 bifunctional effect Effects 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 235000013305 food Nutrition 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 239000002798 polar solvent Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000010839 body fluid Substances 0.000 claims description 4
- 210000000476 body water Anatomy 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 abstract description 22
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 125
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 50
- 239000002904 solvent Substances 0.000 description 38
- 229940126062 Compound A Drugs 0.000 description 36
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 30
- 229920000642 polymer Polymers 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 229910000027 potassium carbonate Inorganic materials 0.000 description 25
- 125000000524 functional group Chemical group 0.000 description 22
- NSGDYZCDUPSTQT-UHFFFAOYSA-N N-[5-bromo-1-[(4-fluorophenyl)methyl]-4-methyl-2-oxopyridin-3-yl]cycloheptanecarboxamide Chemical compound Cc1c(Br)cn(Cc2ccc(F)cc2)c(=O)c1NC(=O)C1CCCCCC1 NSGDYZCDUPSTQT-UHFFFAOYSA-N 0.000 description 20
- 238000009833 condensation Methods 0.000 description 19
- 230000005494 condensation Effects 0.000 description 19
- 239000002245 particle Substances 0.000 description 18
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 13
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 12
- 125000001309 chloro group Chemical group Cl* 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- 239000002585 base Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 239000002202 Polyethylene glycol Substances 0.000 description 8
- 150000001491 aromatic compounds Chemical class 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- 229920002492 poly(sulfone) Polymers 0.000 description 8
- 238000009987 spinning Methods 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 7
- 238000006068 polycondensation reaction Methods 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 6
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- 101100062433 Arabidopsis thaliana DHDPS1 gene Proteins 0.000 description 5
- 239000004695 Polyether sulfone Substances 0.000 description 5
- 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 5
- 230000001276 controlling effect Effects 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 229920006393 polyether sulfone Polymers 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- 238000000108 ultra-filtration Methods 0.000 description 5
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 4
- 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 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000011324 bead Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 238000001523 electrospinning Methods 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 229920012287 polyphenylene sulfone Polymers 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 238000001471 micro-filtration Methods 0.000 description 3
- 238000001728 nano-filtration Methods 0.000 description 3
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical class O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- BRPSWMCDEYMRPE-UHFFFAOYSA-N 4-[1,1-bis(4-hydroxyphenyl)ethyl]phenol Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=C(O)C=C1 BRPSWMCDEYMRPE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 150000001348 alkyl chlorides Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- IMHDGJOMLMDPJN-UHFFFAOYSA-N biphenyl-2,2'-diol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- 238000000502 dialysis Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 230000004907 flux Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 239000012510 hollow fiber Substances 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 230000001788 irregular Effects 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000008267 milk Substances 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
- 210000004080 milk Anatomy 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 2
- 125000004957 naphthylene group Chemical group 0.000 description 2
- 239000004745 nonwoven fabric Substances 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- 229910021642 ultra pure water Inorganic materials 0.000 description 2
- 239000012498 ultrapure water Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 1
- KPRRZWRPYOEXGI-UHFFFAOYSA-N 1,3,5-tris[(4-chlorophenyl)sulfonyl]benzene Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(S(=O)(=O)C=2C=CC(Cl)=CC=2)=CC(S(=O)(=O)C=2C=CC(Cl)=CC=2)=C1 KPRRZWRPYOEXGI-UHFFFAOYSA-N 0.000 description 1
- QWXCUYQKJWUGJS-UHFFFAOYSA-N 1,3-bis[(4-chlorophenyl)sulfonyl]benzene Chemical group C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=CC(S(=O)(=O)C=2C=CC(Cl)=CC=2)=C1 QWXCUYQKJWUGJS-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 1
- JAYCNKDKIKZTAF-UHFFFAOYSA-N 1-chloro-2-(2-chlorophenyl)benzene Chemical group ClC1=CC=CC=C1C1=CC=CC=C1Cl JAYCNKDKIKZTAF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- MAQOZOILPAMFSW-UHFFFAOYSA-N 2,6-bis[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=C(CC=3C(=CC=C(C)C=3)O)C=C(C)C=2)O)=C1 MAQOZOILPAMFSW-UHFFFAOYSA-N 0.000 description 1
- VXHYVVAUHMGCEX-UHFFFAOYSA-N 2-(2-hydroxyphenoxy)phenol Chemical class OC1=CC=CC=C1OC1=CC=CC=C1O VXHYVVAUHMGCEX-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- WUQYBSRMWWRFQH-UHFFFAOYSA-N 2-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=CC=C1O WUQYBSRMWWRFQH-UHFFFAOYSA-N 0.000 description 1
- YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical class C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 description 1
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 1
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical class C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 1
- QIOCFZAEFQTCSO-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C=2C=C(C)C(O)=C(C)C=2)(C(F)(F)F)C(F)(F)F)=C1 QIOCFZAEFQTCSO-UHFFFAOYSA-N 0.000 description 1
- RQTDWDATSAVLOR-UHFFFAOYSA-N 4-[3,5-bis(4-hydroxyphenyl)phenyl]phenol Chemical compound C1=CC(O)=CC=C1C1=CC(C=2C=CC(O)=CC=2)=CC(C=2C=CC(O)=CC=2)=C1 RQTDWDATSAVLOR-UHFFFAOYSA-N 0.000 description 1
- IQNDEQHJTOJHAK-UHFFFAOYSA-N 4-[4-[2-[4,4-bis(4-hydroxyphenyl)cyclohexyl]propan-2-yl]-1-(4-hydroxyphenyl)cyclohexyl]phenol Chemical compound C1CC(C=2C=CC(O)=CC=2)(C=2C=CC(O)=CC=2)CCC1C(C)(C)C(CC1)CCC1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 IQNDEQHJTOJHAK-UHFFFAOYSA-N 0.000 description 1
- BOCLKUCIZOXUEY-UHFFFAOYSA-N 4-[tris(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 BOCLKUCIZOXUEY-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G65/40—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 from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
- C09D171/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C09D171/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C09D171/12—Polyphenylene oxides
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D181/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur, with or without nitrogen, oxygen, or carbon only; Coating compositions based on polysulfones; Coating compositions based on derivatives of such polymers
- C09D181/06—Polysulfones; Polyethersulfones
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- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
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- D01F6/765—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from other polycondensation products from polyarylene sulfides
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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Landscapes
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- Organic Chemistry (AREA)
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- Life Sciences & Earth Sciences (AREA)
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- Polyethers (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Paints Or Removers (AREA)
Abstract
Description
A) 少なくとも1種の三官能価以上の化合物と、
B) イソソルビド、イソマンニド、イソイジドまたはそれらの混合物と
を重合形態で含むポリアリーレンエーテルであって、ポリアリーレンエーテルスルホンまたはポリアリーレンエーテルケトンである、ポリアリーレンエーテルが開示されている。
化合物Aは、少なくとも1種の三官能価以上の化合物であり、
化合物Bは、イソソルビド、イソマンニド、イソイジドまたはそれらの混合物であり、
ジオールC1は、化合物Bではない、2個のヒドロキシ基を有する少なくとも1種の化合物であり、
化合物C2は、少なくとも1種のジクロロジアリールスルホンもしくはジクロロジアリールケトン、またはそれらの混合物を含む少なくとも1種(least one)の化合物であり、
出発化合物は、重合される前には、化合物A、B、C2、および存在する場合、ジオールC1であり、
化合物Dは、ポリマー鎖中の反応性基に対して反応性がある1個の官能基を有する少なくとも1種の化合物であり、
溶媒Lは、少なくとも1種の溶媒である。
− ジヒドロキシベンゼン、とりわけヒドロキノンおよびレゾルシノール;
− ジヒドロキシナフタレン、とりわけ1,5−ジヒドロキシナフタレン,1,6−ジヒドロキシナフタレン、1,7−ジヒドロキシナフタレンおよび2,7−ジヒドロキシナフタレン;
− ジヒドロキシビフェニル、とりわけ4,4’−ビフェノールおよび2,2’−ビフェノール;
− ビスフェニルエーテル、とりわけビス(4−ヒドロキシフェニル)エーテルおよびビス(2−ヒドロキシフェニル)エーテル;
− ビスフェニルプロパン、とりわけ2,2−ビス(4−ヒドロキシフェニル)プロパン、2,2−ビス(3−メチル−4−ヒドロキシフェニル)プロパンおよび2,2−ビス(3,5−ジメチル−4−ヒドロキシ−フェニル)プロパン;
− ビスフェニルメタン、とりわけビス(4−ヒドロキシフェニル)メタン;
− ビスフェニルスルホン、とりわけビス(4−ヒドロキシフェニル)スルホン;
− ビスフェニルスルフィド、とりわけビス(4−ヒドロキシフェニル)スルフィド;
− ビスフェニルケトン、とりわけビス(4−ヒドロキシフェニル)ケトン;
− ビスフェニルヘキサフルオロプロパン、とりわけ2,2−ビス(3,5−ジメチル−4−ヒドロキシフェニル)ヘキサフルオロプロパン;および
− ビスフェニルフルオレン、とりわけ9,9−ビス(4−ヒドロキシフェニル)フルオレン。
(式中、記号t、q、Q、T、Y、ArおよびAr1の定義は、以下の通りである:
r:0または1であり
t、q:互いに独立して、0または1または2または3であり
Q、T、Y:互いに独立して、各場合において、化学結合、または−O−、−S−、−SO2−、S=O、C=O、−N=N−および−CRaRb−(式中、RaおよびRbは、互いに独立して、各場合において、水素原子またはC1〜C12−アルキル、C1〜C12−アルコキシ、C3〜C12−シクロアルキルもしくはC6〜C18−アリール基である)から選択される基であり、Q、TおよびYの少なくとも1個は、−SO2−または−CO−であり、
Z:ISOSO、ISOMAまたはISOIDに由来する基であり、
ArおよびAr1:互いに独立して、6〜18個の炭素原子を有するアリーレン基である)
を含むことが好ましくあり得る。
a)少なくとも1種の三官能価以上の化合物(化合物A)、および
b)イソソルビド、イソマンニド、イソイジドまたはそれらの混合物(化合物B)
を
c)少なくとも1種のジクロロジアリールスルホンもしくはジクロロジアリールケトン、またはそれらの混合物を含む少なくとも1種の二官能価化合物(化合物C2)と
反応させる工程を含む方法により有利なことに製造され得る。
反応時間: 反応混合物が、190℃で維持されている間の時間。
DCDPS: 4,4’−ジクロロジフェニルスルホン
DHDPS 4,4’−ジヒドロキシジフェニルスルホン
BP: 4,4’−ジヒドロキシビフェニル
ISOSO: イソソルビド
THPE 1,1,1−トリスヒドロキシフェニルエタン(trishydroxyphenylethan)
NMP: N−メチル−2−ピロリドン
PVP: ポリビニルピロリドン
PEG: ポリエチレングリコール(polyethylene glycole)
PWP 純粋な水の浸透度
MWCO 分子量のカットオフ
一般手順
撹拌器、ディーン−スターク−トラップ、窒素導入口および温度制御器(control)を備えた容器中、モノマーおよび本発明による実験に関してはさらにTHPEならびに炭酸カリウムをNMP中、窒素雰囲気下で懸濁した。撹拌下で、この混合物を1時間以内に190℃まで加熱した。反応中に形成した水を、蒸留により連続的に除去した。補う溶媒の潜在的喪失をモニタリングした。窒素をこの混合物にパージし、この混合物を縮合時間の間、190℃で維持する。この時間の後、窒素下でNMPを加えて、混合物を室温まで冷却した(1時間以内)。形成した塩化カリウムを除去するため、反応混合物をろ過した。次に、得られたポリマー溶液を水中に沈殿させて、得られたポリマービーズを分離し、次に、熱水(85℃)で20時間、抽出した。次に、ビーズを120℃で24時間、減圧して(<100mbar)乾燥した。
以下の細目を用いる一般手順に従いこの製造を行った:
580.06g(2.02mol)のDCDPS、292.28g(2.00mol)のISOSO、304.05g(2.20mol)の炭酸カリウム(32.4μmの体積平均粒子サイズ)を1050mlのNMP中に懸濁した。
1950mlのNMPを加えて、この混合物を冷却した。
以下の細目を用いる一般手順に従いこの製造を行った:
435,047g(1,515mol)のDCDPS、219.21g(1.50mol)のISOSOおよび269.51g(1.95mol)の炭酸カリウム(8.7μmの体積平均粒子サイズ)を790mlのNMP中に懸濁した。
1460mlのNMPを加えて、この混合物を冷却した。
以下の細目を用いる一般手順に従いこの製造を行った:
435,047g(1,515mol)のDCDPS、212,852g(1,4565mol)のISOSO、9.19g(0.03mol)のTHPE、269.51g(1.95mol)の炭酸カリウム(8.7μmの体積平均粒子サイズ)を790mlのNMP中に懸濁した。
1460mlのNMPを加えて、この混合物を冷却した。
以下の細目を用いる一般手順に従いこの製造を行った:
435,047g(1,515mol)のDCDPS、210,441g(1.44mol)のISOSO、12,254g(0.04mol)のTHPEおよび269.51g(1.95mol)の炭酸カリウム(8.7μmの体積平均粒子サイズ)を790mlのNMP中に懸濁した。
1460mlのNMPを加えて、この混合物を冷却した。
以下の細目を用いる一般手順に従いこの製造を行った:
432.91g(1,5075mol)のDCDPS、219.21g(1.50mol)のISOSO、269.51g(1.95mol)の炭酸カリウム(8.7μmの体積平均粒子サイズ)を790mlのNMP中に懸濁した。
1460mlのNMPを加えて、この混合物を冷却した。
以下の細目を用いる一般手順に従いこの製造を行った:
432.91g(1,5075mol)のDCDPS、219.21g(1.50mol)のISOSO、269.51g(1.95mol)の炭酸カリウム(8.7μmの体積平均粒子サイズ)を650mlのNMP中に懸濁した。
1600mlのNMPを加えて、この混合物を室温まで冷却した。
以下の細目を用いる一般手順に従いこの製造を行った:
432.91g(1,5075mol)のDCDPS、153.48g(1.05mol)のISOSO、112.63g(0.45mol)のDHDPS、269.51g(1.95mol)の炭酸カリウム(8.7μmの体積平均粒子サイズ)を650mlのNMP中に懸濁した。
1600mlのNMPを加えて、この混合物を冷却した。
以下の細目を用いる一般手順に従いこの製造を行った:
432.91g(1,5075mol)のDCDPS、175.37g(1.20mol)のISOSO、75.08g(0,3mol)のDHDPS、269.51g(1.95mol)の炭酸カリウム(8.7μmの体積平均粒子サイズ)を650mlのNMP中に懸濁した。
1600mlのNMPを加えて、この混合物を冷却した。
以下の細目を用いる一般手順に従いこの製造を行った:
432.91g(1,5075mol)のDCDPS、153.48g(1.05mol)のISOSO、101.36g(0.405mol)のDHDPS、9.19g(0.03mol)のTHPE、269.51g(1.95mol)の炭酸カリウム(8.7μmの体積平均粒子サイズ)を650mlのNMP中に懸濁した。
1600mlのNMPを加えて、この混合物を冷却した。
以下の細目を用いる一般手順に従いこの製造を行った:
432.91g(1,5075mol)のDCDPS、175.37g(1.20mol)のISOSO、63.82g(0.255mol)のDHDPS、9.19g(0.03mol)のTHPEおよび269.51g(1.95mol)の炭酸カリウム(8.7μmの体積平均粒子サイズ)を650mlのNMP中に懸濁した。
1600mlのNMPを加えて、この混合物を冷却した。
以下の細目を用いる一般手順に従いこの製造を行った:
432.91g(1,5075mol)のDCDPS、218.18g(1,493mol)のISOSO、1.37g(0.0045mol)のTHPEおよび269.51g(1.95mol)の炭酸カリウム(8.7μmの体積平均粒子サイズ)を650mlのNMP中に懸濁した。
1600mlのNMPを加えて、この混合物を冷却した。
以下の細目を用いる一般手順に従いこの製造を行った:
432.91g(1,5075mol)のDCDPS、201.67g(1.38mol)のISOSO、24.51g(0.08mol)のTHPEおよび269.51g(1.95mol)の炭酸カリウム(8.7μmの体積平均粒子サイズ)を650mlのNMP中に懸濁した。
1600mlのNMPを加えて、この混合物を冷却した。
以下の細目を用いる一般手順に従いこの製造を行った:
577.16g(2.01mol)のDCDPS、146.14g(1.00mol)のISOSO、186.21g(1.00mol)のBPおよび317.88g(2.30mol)の炭酸カリウム(32.7μmの体積平均粒子サイズ)を1050mlのNMP中に懸濁した。
1500mlのNMPを加えて、この混合物を冷却した。
以下の細目を用いる一般手順に従いこの製造を行った:
577.16g(2.01mol)のDCDPS、204.59g(1.40mol)のISOSO、111.73g(0.60mol)のBPおよび317.88g(2.30mol)の炭酸カリウム(32.7μmの体積平均粒子サイズ)を1050mlのNMP中に懸濁した。
1500mlのNMPを加えて、この混合物を冷却した。
以下の細目を用いる一般手順に従いこの製造を行った:
577.16g(2.01mol)のDCDPS、146.14g(1.00mol)のイソソルビド、175.04g(0.94mol)のBP、12.25g(0.04mol)のTHPEおよび317.88g(2.30mol)の炭酸カリウム(32.7μmの体積平均粒子サイズ)を1050mlのNMP中に懸濁した。
1500mlのNMPを加えて、この混合物を冷却した。
以下の細目を用いる一般手順に従いこの製造を行った:
577.16g(2.01mol)のDCDPS、204.59g(1.40mol)のISOSO、100.55g(0.54mol)のBP、12.25g(0.04mol)のTHPEおよび317.88g(2.30mol)の炭酸カリウム(32.7μmの体積平均粒子サイズ)を1050mlのNMP中に懸濁した。
1500mlのNMPを加えて、この混合物を冷却した。
得られたポリマーを、ろ過した反応混合物を液滴に分割して、沈殿用浴にこの液滴を移送することによって単離した。沈殿溶媒は、室温で脱塩水とした。沈殿高さは、0.5mとした。処理能力は、約2.5l/時であった。次に、そのようにして得られたビーズを85℃で20時間、水で抽出した(水の処理能力は160l/時)。この後、ビーズをガラス転移温度(Tg)未満の温度において減圧下で乾燥し、残留水分を0.5質量%未満にした。
キャスト溶液および膜の製造:
磁気撹拌器を備える3つ口フラスコの中に、78mlのNMP、5gのPVP(Luvitec(登録商標)K40)および17gのポリアリーレンエーテルを加えた。均一な濁りのない高粘度溶液が得られるまで、穏やかな撹拌下でこの混合物を60℃に加熱した。この溶液を室温で一晩、脱気した。この後、膜溶液を60℃で2時間、再加熱して、キャスト用ナイフ(300ミクロン)を使用し、5mm/分の速度で操作したErichsenコーティング機器を使用し、60℃でガラスプレートにキャストした。この膜フィルムを30秒間、休ませた後、25℃で10分間、水浴中に浸漬した。
直径60mmを有する圧力セルを使用して、膜のPWPを超純水(Millipore UFシステムによりろ過した塩不含水)を使用して試験した。その後の試験において、1000から1,000,000g/molの範囲の分子量(Mw)に及ぶ様々なPEG標準品の溶液(水中のPEG/PEOが0.1質量%の濃度)を0.15barの圧力でろ過した。フィードおよび透過液のGPC測定により、分子量カットオフを決定した。GPC測定に関して、得られたまま/製造したままの溶液を使用した。固定相としてヒドロキシル化PMMAを有する2本のカラム、およびRI検出器システムを使用し、0.8mL/分の流速において、35℃でGPC測定を行った。
Claims (16)
- A)少なくとも1種の三官能価以上の化合物と、
B)イソソルビド、イソマンニド、イソイジドまたはそれらの混合物と
を重合形態で含むポリアリーレンエーテルであって、ポリアリーレンエーテルスルホンまたはポリアリーレンエーテルケトンである、ポリアリーレンエーテル。 - A)少なくとも1種の三官能価化合物
を含む、請求項1に記載のポリアリーレンエーテル。 - A)少なくとも1種のトリオール
を含む、請求項1または2に記載のポリアリーレンエーテル。 - A)1,1,1−トリスヒドロキシフェニルエタン
を含む、請求項1から3のいずれか一項に記載のポリアリーレンエーテル。 - B)イソソルビド
を含む、請求項1から4のいずれか一項に記載のポリアリーレンエーテル。 - 化合物Bではない、2個のヒドロキシ基を有する少なくとも1種の化合物、ジオールC1)を含む、請求項1から5のいずれか一項に記載のポリアリーレンエーテル。
- A)ポリアリーレンエーテルに含まれる化合物AおよびBならびにジオールC1の総量に対して、0.5から5mol%の少なくとも1種の三官能価以上の化合物
を含む、請求項1から6のいずれか一項に記載のポリアリーレンエーテル。 - 一般式II
t、q:互いに独立して、0、1、2または3であり、
Q、T、Y:互いに独立して、各場合において、化学結合、または−O−、−S−、−SO2−、S=O、C=O、−N=N−および−CRaRb−(式中、RaおよびRbは、互いに独立して、各場合において、水素原子またはC1〜C12−アルキル、C1〜C12−アルコキシもしくはC6〜C18−アリール基である)から選択される基であり、Q、TおよびYの少なくとも1個は、−SO2−または−CO−であり、
Z:イソソルビド、イソマンニド、イソイジドに由来する基であり、
ArおよびAr1:互いに独立して、6〜18個の炭素原子を有するアリーレン基である)
の少なくとも1個の単位を含む、請求項1から7のいずれか一項に記載のポリアリーレンエーテル。 - ポリアリーレンエーテルを製造する方法であって、
a)少なくとも1種の三官能価以上の化合物、および
b)イソソルビド、イソマンニド、イソイジドまたはそれらの混合物
を
c)少なくとも1種のジクロロジアリールスルホン、ジクロロジアリールケトンまたはそれらの混合物を含む二官能価化合物
と反応させる工程を含む、方法。 - 非プロトン性極性溶媒の存在下、共沸混合物を形成する化合物の非存在下でモノマーを反応させる工程を含む、請求項9に記載の方法。
- コーティング、フィルム、繊維、発泡体、膜または成形物品の製造において、請求項1から8のいずれか一項に記載のまたは請求項9もしくは10に記載の方法から得られたポリアリーレンエーテルを使用する方法。
- 膜の製造における、請求項11に記載の使用する方法。
- 請求項1から8のいずれか一項に記載のまたは請求項9もしくは10に記載の方法から得られたポリアリーレンエーテルを含む繊維。
- 請求項1から8のいずれか一項に記載のまたは請求項9もしくは10に記載の方法から得られたポリアリーレンエーテルを含む膜。
- 請求項14に記載の膜を含む物品。
- 水、体液または食品生産における液体と接触して、請求項14に記載の膜または請求項15に記載の物品を使用する方法。
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CN104903383B (zh) | 2012-11-09 | 2017-12-29 | 索尔维特殊聚合物美国有限责任公司 | 聚亚芳基醚砜 |
KR101704475B1 (ko) * | 2014-08-25 | 2017-02-10 | 주식회사 삼양사 | 내열성 및 내화학성이 우수한 폴리술폰 공중합체 및 그 제조방법 |
EP3088442A1 (en) * | 2015-04-30 | 2016-11-02 | Solvay Specialty Polymers USA, LLC. | Polymer compositions based on a bio-sourced polyarylene ether sulfone |
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