CA2741016C - Method for the manufacture of poly(aryl ether ketone)s in the presence of sodium carbonate - Google Patents
Method for the manufacture of poly(aryl ether ketone)s in the presence of sodium carbonate Download PDFInfo
- Publication number
- CA2741016C CA2741016C CA2741016A CA2741016A CA2741016C CA 2741016 C CA2741016 C CA 2741016C CA 2741016 A CA2741016 A CA 2741016A CA 2741016 A CA2741016 A CA 2741016A CA 2741016 C CA2741016 C CA 2741016C
- Authority
- CA
- Canada
- Prior art keywords
- sodium carbonate
- particle size
- poly
- ether ketone
- size distribution
- 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.)
- Expired - Fee Related
Links
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 title claims abstract description 484
- 229910000029 sodium carbonate Inorganic materials 0.000 title claims abstract description 214
- 229920006260 polyaryletherketone Polymers 0.000 title claims abstract description 105
- 238000000034 method Methods 0.000 title claims abstract description 98
- 238000004519 manufacturing process Methods 0.000 title description 7
- 239000002245 particle Substances 0.000 claims abstract description 126
- 238000009826 distribution Methods 0.000 claims abstract description 59
- 229920002530 polyetherether ketone Polymers 0.000 claims abstract description 26
- 238000002360 preparation method Methods 0.000 claims abstract description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 66
- 125000003118 aryl group Chemical group 0.000 claims description 46
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 44
- 238000007873 sieving Methods 0.000 claims description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 32
- 229910001868 water Inorganic materials 0.000 claims description 32
- 239000011734 sodium Substances 0.000 claims description 30
- 239000006184 cosolvent Substances 0.000 claims description 21
- 235000015320 potassium carbonate Nutrition 0.000 claims description 21
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 18
- 239000011575 calcium Substances 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 229910052791 calcium Inorganic materials 0.000 claims description 11
- 238000005259 measurement Methods 0.000 claims description 11
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 10
- 238000000926 separation method Methods 0.000 claims description 4
- 235000017550 sodium carbonate Nutrition 0.000 abstract description 207
- 239000004696 Poly ether ether ketone Substances 0.000 abstract 1
- JUPQTSLXMOCDHR-UHFFFAOYSA-N benzene-1,4-diol;bis(4-fluorophenyl)methanone Chemical compound OC1=CC=C(O)C=C1.C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 JUPQTSLXMOCDHR-UHFFFAOYSA-N 0.000 abstract 1
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 68
- 239000000523 sample Substances 0.000 description 42
- 229920000642 polymer Polymers 0.000 description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 26
- 235000011182 sodium carbonates Nutrition 0.000 description 26
- 239000000843 powder Substances 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 22
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- LSQARZALBDFYQZ-UHFFFAOYSA-N 4,4'-difluorobenzophenone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 LSQARZALBDFYQZ-UHFFFAOYSA-N 0.000 description 18
- 239000012535 impurity Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 16
- -1 K2CO3) either alone Chemical compound 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000000047 product Substances 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
- LKFIWRPOVFNPKR-UHFFFAOYSA-N (2-fluorophenyl)-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=CC=C1F LKFIWRPOVFNPKR-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 235000011181 potassium carbonates Nutrition 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
- 229910052742 iron Inorganic materials 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
- OGTSHGYHILFRHD-UHFFFAOYSA-N (4-fluorophenyl)-phenylmethanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=CC=C1 OGTSHGYHILFRHD-UHFFFAOYSA-N 0.000 description 9
- 230000001955 cumulated effect Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 241000220317 Rosa Species 0.000 description 8
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 229920001643 poly(ether ketone) Polymers 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 7
- 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 7
- 238000009621 Solvay process Methods 0.000 description 7
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 7
- 150000008041 alkali metal carbonates Chemical class 0.000 description 7
- 230000008901 benefit Effects 0.000 description 7
- 239000001569 carbon dioxide Substances 0.000 description 7
- 229910002092 carbon dioxide Inorganic materials 0.000 description 7
- 238000002296 dynamic light scattering Methods 0.000 description 7
- 238000000227 grinding Methods 0.000 description 7
- 229920001519 homopolymer Polymers 0.000 description 7
- 239000011777 magnesium Substances 0.000 description 7
- 230000014759 maintenance of location Effects 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 230000000717 retained effect Effects 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 229910001220 stainless steel Inorganic materials 0.000 description 7
- 239000010935 stainless steel Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 238000005070 sampling Methods 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- 108091006629 SLC13A2 Proteins 0.000 description 5
- 238000001354 calcination Methods 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000006482 condensation reaction Methods 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 description 5
- 230000000269 nucleophilic effect Effects 0.000 description 5
- 239000011591 potassium Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000004448 titration Methods 0.000 description 5
- 241001550224 Apha Species 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000002485 combustion reaction Methods 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 239000012039 electrophile Substances 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 238000010926 purge Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000012901 Milli-Q water Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 230000001186 cumulative effect Effects 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000004811 liquid chromatography Methods 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 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 2
- HLRVUOFDBXRZBI-UHFFFAOYSA-N 4-fluoro-4'-hydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(F)C=C1 HLRVUOFDBXRZBI-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- HVYBCWHAJRYTCH-UHFFFAOYSA-N [3-(4-hydroxybenzoyl)phenyl]-(4-hydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC(C(=O)C=2C=CC(O)=CC=2)=C1 HVYBCWHAJRYTCH-UHFFFAOYSA-N 0.000 description 2
- ADUODNZKKNUWBZ-UHFFFAOYSA-N [4-(4-hydroxybenzoyl)phenyl]-(4-hydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(C(=O)C=2C=CC(O)=CC=2)C=C1 ADUODNZKKNUWBZ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 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 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 235000010216 calcium carbonate Nutrition 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 239000011362 coarse particle Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- 230000004069 differentiation Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 2
- 239000012038 nucleophile Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 238000003921 particle size analysis Methods 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 230000035939 shock Effects 0.000 description 2
- 239000012086 standard solution Substances 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- HFCFFLWPIFNGCX-UHFFFAOYSA-N 2-isocyanato-4-methylthiophene Chemical compound CC1=CSC(N=C=O)=C1 HFCFFLWPIFNGCX-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 1
- 229910013470 LiC1 Inorganic materials 0.000 description 1
- 229920008285 Poly(ether ketone) PEK Polymers 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 241001625808 Trona Species 0.000 description 1
- 239000005083 Zinc sulfide Substances 0.000 description 1
- YRQUJUHGDAXPIQ-UHFFFAOYSA-N [4-(4-fluorobenzoyl)-4-phenylcyclohexa-1,5-dien-1-yl]-(4-fluorophenyl)methanone;[3-(4-fluorobenzoyl)phenyl]-(4-fluorophenyl)methanone Chemical group C1=CC(F)=CC=C1C(=O)C1=CC=CC(C(=O)C=2C=CC(F)=CC=2)=C1.C1=CC(F)=CC=C1C(=O)C1=CCC(C=2C=CC=CC=2)(C(=O)C=2C=CC(F)=CC=2)C=C1 YRQUJUHGDAXPIQ-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 238000004380 ashing Methods 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 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 1
- 239000012490 blank solution Substances 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000000567 combustion gas Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- IKJFYINYNJYDTA-UHFFFAOYSA-N dibenzothiophene sulfone Chemical compound C1=CC=C2S(=O)(=O)C3=CC=CC=C3C2=C1 IKJFYINYNJYDTA-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000009616 inductively coupled plasma Methods 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910052976 metal sulfide Inorganic materials 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 230000000399 orthopedic effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- WPFGFHJALYCVMO-UHFFFAOYSA-L rubidium carbonate Chemical compound [Rb+].[Rb+].[O-]C([O-])=O WPFGFHJALYCVMO-UHFFFAOYSA-L 0.000 description 1
- 229910000026 rubidium carbonate Inorganic materials 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000010187 selection method Methods 0.000 description 1
- 238000005029 sieve analysis Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000012421 spiking Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- WCTAGTRAWPDFQO-UHFFFAOYSA-K trisodium;hydrogen carbonate;carbonate Chemical compound [Na+].[Na+].[Na+].OC([O-])=O.[O-]C([O-])=O WCTAGTRAWPDFQO-UHFFFAOYSA-K 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- 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
- C08G65/4012—Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01D—COMPOUNDS OF ALKALI METALS, i.e. LITHIUM, SODIUM, POTASSIUM, RUBIDIUM, CAESIUM, OR FRANCIUM
- C01D7/00—Carbonates of sodium, potassium or alkali metals in general
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/06—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
-
- 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
- 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
- C08G65/4087—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 characterised by the catalyst used
-
- 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
- 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
- C08G65/4093—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 characterised by the process or apparatus used
-
- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/02—Condensation polymers of aldehydes or ketones with phenols only of ketones
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/34—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain
- C08G2261/344—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing heteroatoms
- C08G2261/3444—Polyethersulfones
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10809608P | 2008-10-24 | 2008-10-24 | |
| US10809708P | 2008-10-24 | 2008-10-24 | |
| US61/108,096 | 2008-10-24 | ||
| US61/108,097 | 2008-10-24 | ||
| US14020508P | 2008-12-23 | 2008-12-23 | |
| US61/140,205 | 2008-12-23 | ||
| PCT/EP2009/064011 WO2010046484A1 (en) | 2008-10-24 | 2009-10-23 | Method for the manufacture of poly(aryl ether ketone)s in the presence of sodium carbonate |
Publications (2)
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| CA2741016A1 CA2741016A1 (en) | 2010-04-29 |
| CA2741016C true CA2741016C (en) | 2016-10-18 |
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| CA2741016A Expired - Fee Related CA2741016C (en) | 2008-10-24 | 2009-10-23 | Method for the manufacture of poly(aryl ether ketone)s in the presence of sodium carbonate |
| CA2740697A Expired - Fee Related CA2740697C (en) | 2008-10-24 | 2009-10-23 | Improved process for preparing a poly(aryl ether ketone)using a high purity 4,4'-difluorobenzophenone |
| CA2740252A Expired - Fee Related CA2740252C (en) | 2008-10-24 | 2009-10-23 | High purity diphenyl sulfone, preparation and use thereof for the preparation of a poly(aryletherketone) |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
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| CA2740697A Expired - Fee Related CA2740697C (en) | 2008-10-24 | 2009-10-23 | Improved process for preparing a poly(aryl ether ketone)using a high purity 4,4'-difluorobenzophenone |
| CA2740252A Expired - Fee Related CA2740252C (en) | 2008-10-24 | 2009-10-23 | High purity diphenyl sulfone, preparation and use thereof for the preparation of a poly(aryletherketone) |
Country Status (8)
| Country | Link |
|---|---|
| US (7) | US8710171B2 (enExample) |
| EP (5) | EP2344565B1 (enExample) |
| JP (5) | JP5734858B2 (enExample) |
| CN (6) | CN102257034B (enExample) |
| AU (1) | AU2009306298A1 (enExample) |
| CA (3) | CA2741016C (enExample) |
| RU (1) | RU2011120794A (enExample) |
| WO (4) | WO2010046483A1 (enExample) |
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| CA2741016C (en) * | 2008-10-24 | 2016-10-18 | Solvay Advanced Polymers, L.L.C. | Method for the manufacture of poly(aryl ether ketone)s in the presence of sodium carbonate |
| CN101580583B (zh) * | 2009-06-26 | 2011-03-30 | 金发科技股份有限公司 | 采用四元共聚技术制备聚芳醚酮类共聚物的方法 |
| JP5646621B2 (ja) | 2009-07-24 | 2014-12-24 | インヴィスタ テクノロジーズ エスアエルエル | イオン性液体を用いた合成方法 |
| WO2013042343A1 (ja) * | 2011-09-21 | 2013-03-28 | 東レ株式会社 | 環式ポリフェニレンエーテルエーテルケトン組成物の回収方法およびそれを用いたポリフェニレンエーテルエーテルケトンの製造方法 |
| CN104870519B (zh) * | 2012-12-21 | 2017-11-24 | 东丽株式会社 | 环式聚苯醚醚酮组合物及线状聚苯醚醚酮的制造方法、聚苯醚醚酮的制造方法 |
| JP6221311B2 (ja) * | 2013-04-05 | 2017-11-01 | 東レ株式会社 | ポリフェニレンエーテルエーテルケトンの製造方法 |
| CN105358605A (zh) * | 2013-05-02 | 2016-02-24 | 巴斯夫欧洲公司 | 聚芳基醚砜共聚物 |
| WO2014177643A1 (de) | 2013-05-02 | 2014-11-06 | Basf Se | Polyarylethersulfoncopolymere |
| GB201311376D0 (en) * | 2013-06-26 | 2013-08-14 | Victrex Mfg Ltd | Polymetric Materials |
| GB2526243B (en) | 2014-02-24 | 2021-07-14 | Victrex Mfg Ltd | Polymeric materials |
| GB201409128D0 (en) * | 2014-05-22 | 2014-07-09 | Ketonex Ltd | Method |
| US20160053107A1 (en) | 2014-08-21 | 2016-02-25 | Ticona Llc | Composition Containing a Polyaryletherketone and Low Naphthenic Liquid Crystalline Polymer |
| MX2017002210A (es) | 2014-08-21 | 2017-05-22 | Ticona Llc | Composicion de poliariletercetona. |
| GB201415972D0 (en) | 2014-09-10 | 2014-10-22 | Ketonex Ltd | Process |
| CN107109222B (zh) * | 2014-12-19 | 2021-05-07 | 默克专利股份有限公司 | 双介晶化合物和介晶介质 |
| US20180009950A1 (en) * | 2015-01-23 | 2018-01-11 | Basf Se | Desalination of polyaryl ethers from a melt polymerization method |
| CN107428932B (zh) * | 2015-01-23 | 2021-06-01 | 巴斯夫欧洲公司 | 利用熔融萃取对聚芳基醚脱盐 |
| EP3222651A1 (de) | 2016-03-21 | 2017-09-27 | Basf Se | Entsalzung von polyarylethern mittels schmelzeextraktion |
| CN109843974B (zh) * | 2016-09-26 | 2022-05-27 | 威格斯制造有限公司 | 聚合物和其制造方法 |
| WO2018086873A1 (en) | 2016-11-11 | 2018-05-17 | Solvay Specialty Polymers Usa, Llc | Polyarylether ketone copolymer |
| CN110177823B (zh) | 2016-11-11 | 2023-04-28 | 索尔维特殊聚合物美国有限责任公司 | 聚芳醚酮共聚物 |
| WO2018115035A1 (en) | 2016-12-21 | 2018-06-28 | Solvay Specialty Polymers Usa, Llc | Poly(ether ketone ketone) polymers, corresponding synthesis methods and polymer compositions and articles made therefrom |
| CN114716665B (zh) | 2016-12-21 | 2024-01-09 | 索尔维特殊聚合物美国有限责任公司 | 聚(醚酮酮)聚合物、相应的合成方法和聚合物组合物以及由其制成的制品 |
| JP7271422B2 (ja) * | 2016-12-21 | 2023-05-11 | ソルベイ スペシャルティ ポリマーズ ユーエスエー， エルエルシー | ビス（ベンゾイル）ベンゼンを含むモノマー組成物中の金属の濃度を低減させるための方法 |
| US11780962B2 (en) | 2016-12-21 | 2023-10-10 | Solvay Specialty Polymers Usa, Llc | Poly(ether ketone ketone) polymers, corresponding synthesis methods and polymer compositions and articles made therefrom |
| WO2018115033A1 (en) | 2016-12-21 | 2018-06-28 | Solvay Specialty Polymers Usa, Llc | Poly(ether ketone ketone) polymers, corresponding synthesis methods and polymer compositions and articles made therefrom |
| US11851526B2 (en) | 2017-06-30 | 2023-12-26 | Solvay Specialty Polymers Usa, Llc | Poly(ether ketone ketone) polymer powder having a low volatiles content |
| US11773218B2 (en) | 2017-12-20 | 2023-10-03 | Solvay Specialty Polymers Usa, Llc | Method of making a PEEK-PEmEK copolymer and copolymer obtained from the method |
| WO2019243433A1 (en) * | 2018-06-21 | 2019-12-26 | Solvay Specialty Polymers Usa, Llc | Poly(ether ketone ketone) (pekk) polymer and composites |
| CN109061026B (zh) * | 2018-09-05 | 2020-12-25 | 九江天赐高新材料有限公司 | 一种对合成的peek样品进行分析检测的方法 |
| WO2020095115A2 (en) | 2018-11-09 | 2020-05-14 | Arkema France | Method for the recovery of compounds deriving from the synthesis of aryl ether ketones |
| US10731001B2 (en) | 2018-11-09 | 2020-08-04 | Arkema France | Method for the recovery of compounds deriving from the synthesis of poly aryl ether ketone polymers |
| EP3650095B1 (en) | 2018-11-09 | 2025-09-03 | Arkema France | Method for the recovery of compounds deriving from the synthesis of aryl ether ketones by evaporation with a rotor |
| CN109725087B (zh) * | 2019-03-16 | 2021-05-14 | 丁立平 | 一种测定纺织品中三种痕量多卤代苯酚的气相色谱-质谱联用法 |
| US11845832B2 (en) | 2019-06-20 | 2023-12-19 | Solvay Specialty Polymers Usa, Llc | Method of making a PEEK-PEoEK copolymer and copolymer obtained from the method |
| EP3986971B1 (en) | 2019-06-20 | 2023-08-09 | Solvay Specialty Polymers USA, LLC. | Polymer-metal junction comprising peek-peoek copolymer compositions, in contact with a metal substrate |
| WO2020254096A1 (en) | 2019-06-20 | 2020-12-24 | Solvay Specialty Polymers Usa, Llc | Peek-peodek copolymer and method of making the copolymer |
| WO2021001132A1 (en) | 2019-07-01 | 2021-01-07 | Solvay Specialty Polymers Usa, Llc | PEEK-PEoEK COPOLYMER POWDER AND METHOD OF PREPARING THE POWDER |
| WO2021008983A1 (en) | 2019-07-12 | 2021-01-21 | Solvay Specialty Polymers Usa, Llc | Fiber reinforced thermoplastic matrix composite material |
| EP4132993A1 (en) | 2020-04-06 | 2023-02-15 | Solvay Specialty Polymers USA, LLC. | Polyarylether ketone polymers |
| US12319785B2 (en) | 2020-09-02 | 2025-06-03 | Idemitsu Kosan Co., Ltd. | Method for producing aromatic polyether, and potassium carbonate used in same |
| TW202219111A (zh) * | 2020-09-02 | 2022-05-16 | 日商出光興產股份有限公司 | 聚醚醚酮之製造方法 |
| WO2022117604A1 (en) * | 2020-12-03 | 2022-06-09 | F. Hoffmann-La Roche Ag | Detection of an analyte of interest by cross spray esi mass spectrometry |
| CN113563578B (zh) * | 2021-08-16 | 2023-12-26 | 吉林省中研高分子材料股份有限公司 | 一种制备聚（芳基醚酮）的方法及聚（芳基醚酮） |
| CN113912799B (zh) * | 2021-09-16 | 2022-05-10 | 吉林省中研高分子材料股份有限公司 | 聚醚醚酮及其制备方法 |
| CN114230785B (zh) * | 2021-11-17 | 2023-03-03 | 吉林省中研高分子材料股份有限公司 | 一种耐辐射的聚醚醚酮聚合物及其制备方法 |
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