GB2172294A - Process for preparing poly(aryl ether ketones) - Google Patents
Process for preparing poly(aryl ether ketones) Download PDFInfo
- Publication number
- GB2172294A GB2172294A GB08605837A GB8605837A GB2172294A GB 2172294 A GB2172294 A GB 2172294A GB 08605837 A GB08605837 A GB 08605837A GB 8605837 A GB8605837 A GB 8605837A GB 2172294 A GB2172294 A GB 2172294A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloride
- bis
- carbonyl
- naphthalene
- diphenyl
- 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.)
- Withdrawn
Links
- -1 poly(aryl ether ketones Chemical class 0.000 title claims abstract description 28
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000002904 solvent Substances 0.000 claims abstract description 15
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 13
- 230000000269 nucleophilic effect Effects 0.000 claims abstract description 10
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims abstract description 8
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 claims abstract description 7
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 claims abstract description 7
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 24
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 10
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 6
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 125000006267 biphenyl group Chemical group 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 3
- FIPTYOFKSOWKTF-UHFFFAOYSA-N 1,2-diphenoxybenzene Chemical compound C=1C=CC=C(OC=2C=CC=CC=2)C=1OC1=CC=CC=C1 FIPTYOFKSOWKTF-UHFFFAOYSA-N 0.000 claims description 2
- JTPSHEWWGCFFLA-UHFFFAOYSA-N 1,2-diphenoxynaphthalene Chemical compound C=1C=C2C=CC=CC2=C(OC=2C=CC=CC=2)C=1OC1=CC=CC=C1 JTPSHEWWGCFFLA-UHFFFAOYSA-N 0.000 claims description 2
- JTNRGGLCSLZOOQ-UHFFFAOYSA-N 1,3-diphenoxybenzene Chemical compound C=1C=CC(OC=2C=CC=CC=2)=CC=1OC1=CC=CC=C1 JTNRGGLCSLZOOQ-UHFFFAOYSA-N 0.000 claims description 2
- UVGPELGZPWDPFP-UHFFFAOYSA-N 1,4-diphenoxybenzene Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1OC1=CC=CC=C1 UVGPELGZPWDPFP-UHFFFAOYSA-N 0.000 claims description 2
- FBPXUTVNRKEJNP-UHFFFAOYSA-N 1-phenoxy-2-(2-phenoxyphenyl)benzene Chemical group C=1C=CC=C(C=2C(=CC=CC=2)OC=2C=CC=CC=2)C=1OC1=CC=CC=C1 FBPXUTVNRKEJNP-UHFFFAOYSA-N 0.000 claims description 2
- RGCAQUUSBHVLJD-UHFFFAOYSA-N 1-phenoxy-4-(4-phenoxyphenyl)benzene Chemical group C=1C=C(C=2C=CC(OC=3C=CC=CC=3)=CC=2)C=CC=1OC1=CC=CC=C1 RGCAQUUSBHVLJD-UHFFFAOYSA-N 0.000 claims description 2
- DABOOAVTBIRGHP-UHFFFAOYSA-N 1-phenoxynaphthalene Chemical compound C=1C=CC2=CC=CC=C2C=1OC1=CC=CC=C1 DABOOAVTBIRGHP-UHFFFAOYSA-N 0.000 claims description 2
- AOOZVQGGMFGGEE-UHFFFAOYSA-N 4-phenoxybenzoyl chloride Chemical group C1=CC(C(=O)Cl)=CC=C1OC1=CC=CC=C1 AOOZVQGGMFGGEE-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 2
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims description 2
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 claims description 2
- IYRWEQXVUNLMAY-UHFFFAOYSA-N carbonyl fluoride Chemical compound FC(F)=O IYRWEQXVUNLMAY-UHFFFAOYSA-N 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 239000004020 conductor Substances 0.000 claims description 2
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 claims description 2
- 238000010292 electrical insulation Methods 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 2
- 238000000465 moulding Methods 0.000 claims description 2
- NFBOHOGPQUYFRF-UHFFFAOYSA-N oxanthrene Chemical compound C1=CC=C2OC3=CC=CC=C3OC2=C1 NFBOHOGPQUYFRF-UHFFFAOYSA-N 0.000 claims description 2
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 claims description 2
- 229920006260 polyaryletherketone Polymers 0.000 claims 6
- MOSLPKHPMJVHDM-UHFFFAOYSA-N 1,5-diphenoxynaphthalene Chemical compound C=1C=CC2=C(OC=3C=CC=CC=3)C=CC=C2C=1OC1=CC=CC=C1 MOSLPKHPMJVHDM-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 11
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 229920001470 polyketone Polymers 0.000 description 9
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 150000004820 halides Chemical class 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- 229910015900 BF3 Inorganic materials 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 125000000777 acyl halide group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- ITVUPWDTDWMACZ-UHFFFAOYSA-N (4-phenoxyphenyl)-phenylmethanone Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 ITVUPWDTDWMACZ-UHFFFAOYSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-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
- JDTMUJBWSGNMGR-UHFFFAOYSA-N 1-nitro-4-phenoxybenzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=CC=C1 JDTMUJBWSGNMGR-UHFFFAOYSA-N 0.000 description 1
- QSBDJCHYJZOIPJ-UHFFFAOYSA-N 2-(2-phenylphenoxy)benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1OC1=CC=CC=C1C1=CC=CC=C1 QSBDJCHYJZOIPJ-UHFFFAOYSA-N 0.000 description 1
- SITZKEFXOJDPOC-UHFFFAOYSA-N 4-(4-phenoxybenzoyl)benzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 SITZKEFXOJDPOC-UHFFFAOYSA-N 0.000 description 1
- ADLJPSKGZARODT-UHFFFAOYSA-N 4-(4-phenoxyphenyl)benzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C(C=C1)=CC=C1OC1=CC=CC=C1 ADLJPSKGZARODT-UHFFFAOYSA-N 0.000 description 1
- OZCULFZQSHFJNI-UHFFFAOYSA-N 4-benzoylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C(=O)C1=CC=CC=C1 OZCULFZQSHFJNI-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- CKYFSKUCBDITLM-UHFFFAOYSA-N C1(=CC=CC=C1)C.C1(=CC=CC=C1)C1=CC=CC=C1.ClC1=CC=CC=C1.FC1=CC=CC=C1.C1(=CC=CC=C1)OC Chemical compound C1(=CC=CC=C1)C.C1(=CC=CC=C1)C1=CC=CC=C1.ClC1=CC=CC=C1.FC1=CC=CC=C1.C1(=CC=CC=C1)OC CKYFSKUCBDITLM-UHFFFAOYSA-N 0.000 description 1
- 101100000858 Caenorhabditis elegans act-3 gene Proteins 0.000 description 1
- 229910021532 Calcite Inorganic materials 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
- BSYGQMVKOODSKE-UHFFFAOYSA-N S(=O)(=O)(Cl)Cl.CC1=CC=CC=C1.S(=O)(=O)(Cl)Cl.ClC1=CC=CC=C1.S(=O)(=O)(Cl)Cl.C1=CC=CC=C1.COC1=CC=C(C(=O)Cl)C=C1.ClC1=CC=C(C(=O)Cl)C=C1.FC1=CC=C(C(=O)Cl)C=C1.C(C1=CC=CC=C1)(=O)Cl Chemical compound S(=O)(=O)(Cl)Cl.CC1=CC=CC=C1.S(=O)(=O)(Cl)Cl.ClC1=CC=CC=C1.S(=O)(=O)(Cl)Cl.C1=CC=CC=C1.COC1=CC=C(C(=O)Cl)C=C1.ClC1=CC=C(C(=O)Cl)C=C1.FC1=CC=C(C(=O)Cl)C=C1.C(C1=CC=CC=C1)(=O)Cl BSYGQMVKOODSKE-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- QXJJQWWVWRCVQT-UHFFFAOYSA-K calcium;sodium;phosphate Chemical compound [Na+].[Ca+2].[O-]P([O-])([O-])=O QXJJQWWVWRCVQT-UHFFFAOYSA-K 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000012764 mineral filler Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- NSNPSJGHTQIXDO-UHFFFAOYSA-N naphthalene-1-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)=CC=CC2=C1 NSNPSJGHTQIXDO-UHFFFAOYSA-N 0.000 description 1
- XNLBCXGRQWUJLU-UHFFFAOYSA-N naphthalene-2-carbonyl chloride Chemical compound C1=CC=CC2=CC(C(=O)Cl)=CC=C21 XNLBCXGRQWUJLU-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000012783 reinforcing fiber Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- 239000003017 thermal stabilizer Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
-
- 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
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/127—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from carbon dioxide, carbonyl halide, carboxylic acids or their derivatives
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Abstract
A process for preparing poly(aryl ether ketones) comprising reacting nucleophilic coreactants with electrophilic coreactants under Friedal Crafts polymerization conditions in a solvent comprising 1,2- dichlorethane. Preferably, diphenyl ether is reacted with terephthaloyl chloride and/or isophthaloyl chloride.
Description
SPECIFICATION
Process for preparing poly(aryl ether ketones)
This invention is directed to an improved process for preparing poly(aryl ether ketones) by reacting a nucleophilic coreactant with an electrophilic coreactant under Friedel-Crafts polymerization conditions, wherein the improvement comprises carrying out the polymerization in a solvent comprising 1,2-dichloroethane.
The preparation of poly(aryl ether ketones) by Friedel-Crafts polymerization techniques is well known in the art. For example, U. S. Patent No. 3,065,205 describes the preparation of aromatic polyketones by Friedel-Crafts polymerization techniques using an organic solvent for the reaction. The solvents used are nitrobenzene, symmetrical tetrachloroethane, dichlorobenzene or carbon disulfide. Nitrobenzene is used as a solvent in all of the examples. The reaction mixture is stated as remaining homogeneous throughout the polymerization. However, the process described in U.S. Patent No. 3,065,205 produces polymers of very low molecular weights and inherent viscosities ranging from 0.13 to 0.18, as measured in concentrated sulfuric acid.
In describing the difficulty in preparing polyketones such as those described in U. S. Patent
No. 3,065,205, U.S. Patent No. 3,791,890 states the problem as the relatively intractable nature of the initial polymer-catalyst complex upon formation. The patent states the following in column 1, lines 10 to 20:
"Previous attempts to deal with the generally intractable state of the reaction product have
included polymerizing the monomers in the presence of a soluble solid material to permit
removing the product from the reaction medium and subsequently separating the soluble
material by leaching. However, none of these prior techniques has proved entirely satisfac tory." In U. S. Patent No. 3,791,890, an improved process is described in which polyketones are prepared in granular form in a two step process.In the first step diphenyl ether and at least one of terephthalic or isophthalic acid chlorides are reacted in the presence of o-dichlorobenzene, sym-tetrachloroethane, or dichloroethane as a solvent utilizing a Friedel-Crafts catalyst, such as aluminum chloride, at a temperature of from - 1 50C to OOC. All the examples use o-dichlorobenzene as the solvent. The patent states that an initial low reaction temperature is desirable to maintain control over the rate of reaction so that coagulation of the formed polyketone does not occur before dispersion can be effected.In the next step, the reaction mixture produced is dispersed into a fluid medium maintained at a temperature of at least 50"C. The fluid medium is described as any gas or liquid in which the polyketone formed is substantially unreactive at the temperature employed in the process. The dispersion into a heated fluid is stated to segregate the particles of polymer that are beginning to form in the initial reaction mixture and prevent the agglomeration of the particles into a gelatinous mass. A granular polyketone is thus recovered.
However, in this patent no viscosities for the polyketone are reported.
In U.S. Patent No. 3,668,057 describes the preparation of copolyketones with reduced viscosities of about 0.9 dl/g (as measured in concentrated sulfuric acid at 25"C) under Freidel-Crafts polymerization conditions with o-dichlorobenzene as solvent. However, polymers with reduced viscosities of about 0.9dl/g are boarderline with regard to toughness in same end-use applications. Copolyketones with high reduced viscosities are possible using hydrofluoric acid as the solvent and boron trifluoride as the catalyst. However, due to the toxicity of hydrofluoric acid/boron trifluoride it is not a system which is conductive to commercialization.
In the present invention a one step process to prepare high molecular weight poly(aryl ether ketones) has been discovered. It has been found that the use of 1,2-dichloroethane as a solvent in Friedel-Crafts polymerization process produces poly(aryl ether ketones) of high molecular weight in comparison to processes where solvents such as nitrobenzene and o-dichlorobenzene are utilized. The process of this invention prepares higher molecular weight (reduced viscosity) poly (aryl ether ketones) directly without the need of the dispersion step as required in U.S.
Patent No. 3,791,890.
The poly(aryl ether ketones) prepared by the process of this invention have reduced viscosities ranging from about 0.1 dl/g to about 3.0 dl/g, preferably from about 0.5 dl/g to about 2.0 dl/g., as measured in concentrated sulfuric acid at 25"C (concentration of 1g/100ml).
The poly(aryl ether ketones) may be prepared by reacting:
(a) a mixture of substantially equimolar amounts of
(i) at least one electrophilic aromatic diacyl halide of the formula
YOC-Ar-COY where -Ar- is a divalent aromatic radical such as phenylene, diphenylether-4,4'-diyl, diphenyl 4,4'-diyl, naphthalene-diyl, and the like, Y is halogen such as chlorine, bromine or iodine with chlorine being preferred, and COY is an aromatically bound acyl halide group, which diacyl halide is polymerizable with at least one aromatic compound of (a)(ii), and
(ii) at least one aromatic nucleophilic compound of the formula
H-Ar'-H where -Ar'- is a divalent aromatic radical such as diphenylether-4,4'-diyl, 2,7-dibenzofuranediyl, diphenyl-4,4'-diyl, diphenylmethane-4,4'-diyl, naphthalene-diyl, phenanthrenediyl, and the like, and
H is an aromatically bound hydrogen atom, which compound is polymerizable with at least one diacyl halide of (a)(i), and
(b) at least one aromatic monoacyl halide of formula
H-Ar"-COY where -Ar"- is a divalent aromatic radical such as diphenylether-4,4'-diyl, diphenylmethane -4,4'diyl, naphthalene-diyl, diphenyl-4,4'-diyl, 2,7-dibenzofuranediyl, and the like, and H is an aromatically bound hydrogen atom, Y is as defined above, and COY is an aromatically bound acyl halide group, which monoacyl halide is self-polymerizable, and
(c) a combination of (a) and (b).
Specifically, the polyketones may be prepared by reacting one or more of the following nucleophilic coreactants: diphenyl sulfide, dibenzofuran, thianthrene, phenoxathin, phenodioxin, diphenylene, diphenyl, dibenzodioxine, xanthone, 4,4'-diphenoxybiphenyl, 2,2'-diphenoxybiphenyl, 1,2-diphenoxybenzene, 1,3-diphenoxybenzene, 1,4-diphenoxybenzene, 1-phenoxynaphthalene, 1 ,2-diphenoxynaphthalene, diphenyl ether, 1 ,5-diphenoxynapthalene.
Similarly, the following electrophilic aromatic coreactant candidates for polyketone formation may be useful: terephthaloyl chloride, isophthaloyl chloride, thio-bis(4,4'-benzoyl chloride), benzophenone-4,4'-di(carbonyl chloride), oxy-bis(4,4'-benzoyl chloride), oxy-bis(3 ,3'-benzoyl chloride), diphenyl-3,3'-di(carbonyl chloride), carbonyl-bis(3,3'-benzoyl chloride), sulfonyl-bis(4,4'-benzoyl chloride), sulfonyl-bis(3,3'-benzoyl chloride), sulfonyl-bis(3,4'-benzoyl chloride), thio-bis(3,4'-benzoyl chloride), diphenyl-3,4'-di(carbonyl chloride), oxy-bis[4,4'-(2-chlorobenzoyl chloride)], naphthalene-1 ,6-di(carbonyl chloride), naphthalene-1 ,7-di(carbonyl chloride), naphthalene-1 ,5-di(carbonyl chloride), naphthalene-2,6-di(carbonyl chloride), oxy-bis[7,7'-naphthalene-2,2'-di(carbonyl chloride)], thio-bis[8,8'-naphthalene-2,2'-di(carbonyl chloride)], 7,7'-binaphthyl-2,2'-di(carbonyl chloride), diphenyl-4,4'-di(carbonyl chloride), carbonyl bis[7,7'-naphthalene-2,2'-di(carbonyl chloride)], sulfonyl-bis[6,6'-naphthalene-2,2'-di(carbonyl chloride)], dibenzofuran-2,7-di(carbonyl chloride) and the like, or the combination of any of the above.
In addition to the electrophilic aromatic coreactants carbonyl chloride (phosgene), carbonyl dibromide, carbonyl difluoride or oxalyl chloride may be used.
Examples of compounds corresponding to the formula H-Ar"-COY include p-phenoxybenzoyl chloride, p-biphenyloxybenzoyl chloride, 4-(p-phenoxyphenyl) benzoyl chloride, 4-(p-phenoxybenzoyl) benzoyl chloride, 4(p-phenoxyphenoxy) benzoyl chloride 3-chlorocarbinyl dibenzofuran, 1naphthoyl chloride, 2-naphthoyl chloride, and the like.
Preferably, diphenyl ether is reacted with terephthaloyl chloride and/or isophthaloyl chloride.
The preferred Friedel-Crafts catalysts are aluminum chloride, antimony pentachloride and ferric chloride. Other Friedel-Crafts catalysts, such as aluminum bromide, boron trifluoride, zinc chloride, antimony trichloride, ferric bromide and stannic chloride, can also be used.
The reaction may be carried out over a range of temperatures of from about 0 C. to about 160"C. In general, it is preferred to carry out the reaction at a temperature in the range of between 0 and 30"C. However, in some cases it is advantageous to carry out the reaction at temperatures above 30"C. or below 0 C. The reaction is generally carried out at ambient pressure. However, in some instances it may be advantageous to carry out the reaction at pressures greater than atmospheric or at subatmospheric pressures.
The reaction is carried out in a solvent system containing at least 50 percent by weight of 1,2-dichloroethane.
The reaction may be carried out in the presence of a capping agent as described in U. S.
Patent Application Serial No. (D-14604) filed on an even date as this application in the name of
L. M. presca and titled, "A Method For Stabilizing Poly(Aryl Ether Ketones)", commonly assigned.
Said application is directed to a method of stabilizing poly(aryl ether ketones) by reacting nucleophilic coreactants with electrophilic coreactants under heterogeneous Friedel-Crafts polymerization conditions by adding a nucleophilic and/or electrophilic capping agent during polymeri zation.
The nucleophilic capping agents are of the general formula:
wherein x is a covalent bond, -0-, -S-, or -CR2- wherein each R is independently hydrogen, an alkyl or fluoroalkyl group, preferably of 1 to 10 carbons, phenyl or an electron withdrawing group substituted phenyl. Preferably, x is a covalent bond, or 0, y is NO2,
or if x is a covalent bond, y can also be hydrogen as well as any of the foregoing,
z is halogen, alkyl or alkoxy
Specific examples of appropriate nucleophilic capping agents are
4-nitrodiphenyl ether
4-phenoxybenzophenone
4-phenoxydiphenyl sulfone
anisole
fluorobenzene
chlorobenzene
biphenyl
toluene.
acetyl chloride
The electrophilic capping agents correspond to the formula
where w=halogen, alkyl, alkoxy, nitro,
Specific examples of these end capping agents include the following
benzoyl chloride
p-fluorobenzoyl chloride
p-chlorobenzoyl chloride
p-methoxybenzoyl chloride
benzene sulfonyl chloride
p-chlorobenzene sulfonyl chloride
p-methylbenzene sulfonyl chloride
4-benzoyl-benzoyl chloride
The capping agents may be added anytime during or after the polymerization reaction but preferably are added with the reactants at the beginning of the polymerization reaction.
The polymer of this invention may include mineral fillers such as carbonates including chalk, calcite and dolomite; silicates including mica, talc, wollastonite; silicon dioxide; glass spheres' glass powders; aluminum; clay; quartz; and the like. Also, reinforcing fibers such as fiberglass, carbon fibers, and the like may be used. The polymers may also include additives such as titanium dioxide; thermal stabilizers, ultraviolet light stabilizers, plasticizers, and the like.
The polymers of this invention may be fabricated into any desired shape, i.e., moldings, coatings, films or fibers. They are particularly desirable for use as electrical insulation for electrical conductors.
EXAMPLES
The following examples serve to give specific illustrations of the practice of this invention but they are not intended in any way to limit the scope of this invention.
Example I
A 2 liter, 3 neck, round bottom flask was equipped with a mechanical stirrer, a nitrogen inlet, condenser and a thermometer. The flask was charged with 14.21 g (0.07 moles) of terephthaloyl chloride, 6.09 9 (0.030 moles) of isophthaloyl chloride, 17.01 9 (0.100 moles) of diphenyl ether and 700 mls of 1,2-dichloroethane. This solution was cooled to 5"C in an ice water bath.
Aluminum chloride (34.76 g, 0.260 moles) was added in portions while maintaining the temperature below 10 C. The resulting reaction mixture was held at 5"-10"C for 6 hours. After 30 minutes a precipitate formed. At the end of 6 hours the ice bath was removed and the reaction mixture was allowed to warm to ambient temperatures (--25"C) where it was held for an additional 16 hours. The reaction mixture was poured into 3 liters of ice water containing 100 ml of concentrated hydrochloric acid. The resulting three phase system was heated to --85"C to distill the 1,2-dichloroethane.The polymer was isolated by filtration, washed with water (2X500 ml) and methanol (2X500 ml) and dried in a vacuum oven at 100"C. The product had a reduced viscosity of 1.62 dl/g as measured in concentrated sulfuric acid at 25"C and a concentration of 9/100 ml.
Comparative Examples A-M
Example 1 was repeated using a variety of solvents, including those well known to be useful in Friedel-Crafts reactions. The results are summarized in Table 1.
TABLE 1
Reduced
Viscosity
of Final
Example Solvent Polymer (dl/g)
A Carbon Disulfide 0.06
B 1,1,1-Trichloroethane 0.07
C Methylene Chloride 0.50
D Methylene Chloride' 0.92
E Carbon Tetrachloride 0.07
F Trichloroethylene 0.17
G Nitrobenzene 0.18
H O-Dichlorobenzene 0.31
O-Dichlorobenzene2 0.47
J O-Dichlorobenzene3 0.51
K 1,2,4-Trichlorobenzene 0.09
L Trichlorofluoromethane 0.05
M 1,1 ,2-Trichlorotrifluoroethane 0.04 '1% excess of diphenyl ether was used 2Four hours at 80"C instead of 16 hours at 25"C 3Six hours at 80"C instead of 16 hours at 25"C Although relatively high molecular weight polymers can be prepared using methylene chloride, this solvent participates in the reaction resulting in alkylation of the polymer backbone as a major side product. Excess diphenyl ether is needed to obtain high molecular weight product because of this side reaction which consumes diphenyl ether and disrupts the reaction stoichiometry. These alkylated side products lead to polymer instability at elevated temperatures.
Examples 2-7
Example 1 was repeated except that a capping agent was added to control the molecular weight of polymer. The stoichiometry of the primary reactants is shown in the equation:
0 9 0 Cl-C + 04) +2X oC-Ct c-c Act 3 1.2 dichloroethane 5"-25"C ocAoococ3Rowco Reduced viscosity as a function of the end capping agent concentration is shown in Table 2.
TABLE 2
Terephthaloyl
Chloride/ Isophthaloyl Reduced
Example Chloride X Viscosity
2 90/10 .003 1.21
3 100/0 .003 1.46
4 95/5 .005 .83
5 95/5 .015 .58
6 95/5 .025 .54
7 90/10 .025 .49
8 100/0 .025 .55
9 90/10 .050 .36
10 90/10 .050 .36
11 100/0 .050 .39
12 100/0 .050 .39
Claims (11)
1. A process for preparing a poly(aryl ether ketone) by reacting nucleophilic coreactants with electrophilic coreactants under Friedel-Crafts polymerization conditions, wherein the process is carried out in a solvent comprising 1,2-dichloroethane.
2. A process as claimed in claim 1 wherein the poly(aryl ether ketone) is prepared by reacting one or more of the following nucleophilic coreactants: diphenyl sulfide, dibenzofuran, thianthrene, phenoxathin, phenodioxin, diphenylene, diphenyl, 4,4'-diphenoxybiphenyl, 2,2'-diphenoxylbiphenyl, 1 ,2-diphenoxybenzene, 1 ,3-diphenoxybenzene, 1 ,4-diphenoxybenzene, 1-phenoxy- naphthalene, 1 ,2-diphenoxynaphthalene, diphenyl ether, or 1 ,5-diphenoxynaphthalene.
3. A process as claimed in claim 1 or claim 2 wherein the poly(aryl ether ketone) is prepared by reacting one or more of the following electrophilic coreactants: phosgene, carbonyl difluoride, terephthaloyl chloride, isophthaloyl chloride, thio-bis(4,4'-benzoyl chloride), benzophenone-4,4'-di(carbonyl chloride), oxy-bis(4,4'-benzoyl chloride), oxy-bis(3,3'-benzoyl chloride), diphenyl-3,3'-di(carbonyl chloride), carbonyl-bis(3,3'-benzoyl chloride), sulfonyl-bis(4,4'-benzoyl chloride), sulfonyl-bis(3,3'-benzoyl chloride), sulfonyl-bis(3,4'-benzoyl chloride), thio-bis(3,4'-benzoyl chloride), diphenyl-3,4'-di(carbonyl chloride), diphenyl-4,4'-di(carbonyi chloride), oxy-bis[4,4'-(2-chlorobenzoyl chloride)], naphthalene-1 ,5-di(carbonyl chloride), naphthalene-1 ,6-di(carbonyl chloride), naphthalene-1,7-di(carbonyl chloride), naphthalene-2,6'-di(carbonyl chloride), oxy-bis[7,7'-naphthalene-2,2'-di(carbonyl chloride)], thio-bis[8,8'-naphthalene-2,2'-di(carbonyl chloride)], 7,7'-binaphthyl-2'-di(carbonyl chloride), carbonyl-bis[7,7'-naphthalene-2,2'-di(carbonyl chloride)], sulfonyl-bis[6,6'-naphthalene-2,2'-di(carbo- nyl chloride)], or dibenzofuran-2,7-di(carbonyl chloride).
4. A process as claimed in claim 1 wherein the reactant and/or coreactant is selected from 4-phenoxybenzoyl chloride, 1-phenoxy-1-naphthalene carbonyl chloride, 4-phenoxy-4'-chlorocarbonyl diphenyl or 4-phenoxy-3'-chlorocarbonyl diphenyl ether.
5. A process as claimed in claim 1 wherein diphenyl ether is reacted with terephthaloyl chloride and/or isophthaloyl chloride.
6. A process as claimed in any one of the preceding claims wherein the process is carried out in the presence of a Freidel-Crafts catalyst selected from aluminium chloride, antimony pentachloride or ferric chloride.
7. A process as claimed in any one of the preceding claims wherein the process is carried out at a temperature of from about 0 C to about 25"C.
8. A process as claimed in claim 1 substantially as hereinbefore described in any one of
Examples 1 to 7.
9. A poly(aryl ether ketone) whenever prepared by a process as claimed in any one of the preceding claims.
10. Mouldings, coatings, films or fibers whenever made from a poly(aryl ether ketone) as claimed in claim 9.
11. Electrical insulation for electrical conductors whenever comprising a poly(aryl ether ketone) as claimed in claim 9.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71011985A | 1985-03-11 | 1985-03-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB8605837D0 GB8605837D0 (en) | 1986-04-16 |
| GB2172294A true GB2172294A (en) | 1986-09-17 |
Family
ID=24852705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08605837A Withdrawn GB2172294A (en) | 1985-03-11 | 1986-03-10 | Process for preparing poly(aryl ether ketones) |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS61211336A (en) |
| CA (1) | CA1246297A (en) |
| DE (1) | DE3607902A1 (en) |
| GB (1) | GB2172294A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1989004848A1 (en) * | 1987-11-17 | 1989-06-01 | Raychem Limited | Preparation of poly(arylene ether ketones) |
| US4918237A (en) * | 1989-03-13 | 1990-04-17 | E. I. Du Pont De Nemours And Company | Process for the manufacture of 1,4-bis(4-phenoxybenzoyl)benzene with certain metal-containing catalysts |
| EP0315441A3 (en) * | 1987-11-04 | 1990-07-18 | Raychem Limited | Poly(arylene ether ketones) |
| EP0390325A3 (en) * | 1989-02-27 | 1991-08-21 | Imperial Chemical Industries Plc | Polyarylketones |
| GB2364319A (en) * | 2000-07-06 | 2002-01-23 | Gharda Chemicals Ltd | Melt processable polyether ether ketone polymer |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991013929A1 (en) * | 1990-03-16 | 1991-09-19 | Asahi Kasei Kogyo Kabushiki Kaisha | Noncrystalline polymers and production thereof |
| CN103665368B (en) * | 2013-11-28 | 2017-01-11 | 张家港祥成医用材料科技有限公司 | Method for low-temperature synthesis of polyaryletherketone resin on nanometer/micrometer-scale inorganic seedbed |
| ES2829265T3 (en) * | 2017-05-16 | 2021-05-31 | Arkema France | Method for making 1,4-bis (4-phenoxybenzoyl) benzene at an elevated temperature |
| EP3404011B1 (en) * | 2017-05-18 | 2020-08-26 | Arkema France | Dissociation of a 1,4-bis(4-phenoxybenzoyl)benzene-lewis acid-complex in an aqueous solution |
| EP3404012B1 (en) | 2017-05-18 | 2020-09-09 | Arkema France | Ripening of 1,4-bis (4-phenoxybenzoyl)benzene |
| KR102262524B1 (en) | 2017-11-16 | 2021-06-07 | 한화솔루션 주식회사 | Method for preparing poly ether ketone ketone |
| EP3650433B1 (en) | 2018-11-09 | 2024-04-24 | Arkema France | Method for manufacturing 1,4-bis (4-phenoxybenzoylbenzene) at an elevated temperature |
| CN119524818A (en) * | 2025-01-23 | 2025-02-28 | 陕西煤基特种燃料研究院有限公司 | A COP@SiO2 solid phase adsorbent based on oil dearomatization, a solid phase extraction column based thereon, and a preparation method and application thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1250225A (en) * | 1968-02-05 | 1971-10-20 | ||
| GB1340709A (en) * | 1970-06-10 | 1973-12-12 | Du Pont | Process for producing crystalline copolyketone films and insulated electrical conductors |
| GB1387303A (en) * | 1971-02-16 | 1975-03-12 | Raychem Corp | Polymers |
| GB2138433A (en) * | 1983-03-31 | 1984-10-24 | Raychem Corp | Preparation of poly (arylene ether ketones) |
| EP0135938A2 (en) * | 1983-09-29 | 1985-04-03 | Mitsubishi Kasei Corporation | Process for producing aromatic polyether ketones and polythioether ketones |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3791890A (en) * | 1972-02-18 | 1974-02-12 | Du Pont | Granualr polyketone preparation |
-
1986
- 1986-02-28 CA CA000503032A patent/CA1246297A/en not_active Expired
- 1986-03-10 GB GB08605837A patent/GB2172294A/en not_active Withdrawn
- 1986-03-10 DE DE19863607902 patent/DE3607902A1/en not_active Ceased
- 1986-03-10 JP JP5073786A patent/JPS61211336A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1250225A (en) * | 1968-02-05 | 1971-10-20 | ||
| GB1340709A (en) * | 1970-06-10 | 1973-12-12 | Du Pont | Process for producing crystalline copolyketone films and insulated electrical conductors |
| GB1387303A (en) * | 1971-02-16 | 1975-03-12 | Raychem Corp | Polymers |
| GB2138433A (en) * | 1983-03-31 | 1984-10-24 | Raychem Corp | Preparation of poly (arylene ether ketones) |
| EP0124276A2 (en) * | 1983-03-31 | 1984-11-07 | RAYCHEM CORPORATION (a Delaware corporation) | Preparation of aromatic polymers |
| EP0135938A2 (en) * | 1983-09-29 | 1985-04-03 | Mitsubishi Kasei Corporation | Process for producing aromatic polyether ketones and polythioether ketones |
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| Title |
|---|
| WO A1 84/03891 * |
| WO A1 84/03892 * |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0315441A3 (en) * | 1987-11-04 | 1990-07-18 | Raychem Limited | Poly(arylene ether ketones) |
| US4990589A (en) * | 1987-11-04 | 1991-02-05 | Raychem Limited | Poly(arylene ether ketones) |
| WO1989004848A1 (en) * | 1987-11-17 | 1989-06-01 | Raychem Limited | Preparation of poly(arylene ether ketones) |
| US5145938A (en) * | 1987-11-17 | 1992-09-08 | Raychem Limited | Preparation of poly(arylene ether ketones) |
| EP0390325A3 (en) * | 1989-02-27 | 1991-08-21 | Imperial Chemical Industries Plc | Polyarylketones |
| US4918237A (en) * | 1989-03-13 | 1990-04-17 | E. I. Du Pont De Nemours And Company | Process for the manufacture of 1,4-bis(4-phenoxybenzoyl)benzene with certain metal-containing catalysts |
| GB2364319A (en) * | 2000-07-06 | 2002-01-23 | Gharda Chemicals Ltd | Melt processable polyether ether ketone polymer |
| GB2364319B (en) * | 2000-07-06 | 2003-01-15 | Gharda Chemicals Ltd | Melt processible polyether ether ketone polymer |
| US6566484B2 (en) | 2000-07-06 | 2003-05-20 | Gharda Chemicals Ltd. | Melt processible polyether ether ketone polymer |
| US6881816B2 (en) | 2000-07-06 | 2005-04-19 | Gharda Chemicals Ltd. | Melt processible polyether ether ketone polymer |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61211336A (en) | 1986-09-19 |
| DE3607902A1 (en) | 1986-09-11 |
| GB8605837D0 (en) | 1986-04-16 |
| CA1246297A (en) | 1988-12-06 |
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