JPH0428732B2 - - Google Patents
Info
- Publication number
- JPH0428732B2 JPH0428732B2 JP63308707A JP30870788A JPH0428732B2 JP H0428732 B2 JPH0428732 B2 JP H0428732B2 JP 63308707 A JP63308707 A JP 63308707A JP 30870788 A JP30870788 A JP 30870788A JP H0428732 B2 JPH0428732 B2 JP H0428732B2
- Authority
- JP
- Japan
- Prior art keywords
- capping agent
- monomer
- polymer
- nucleophilic
- electrophilic
- 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 - Lifetime
Links
- 229920000642 polymer Polymers 0.000 claims description 97
- 239000003795 chemical substances by application Substances 0.000 claims description 79
- 230000000269 nucleophilic effect Effects 0.000 claims description 49
- 239000000178 monomer Substances 0.000 claims description 44
- 238000006116 polymerization reaction Methods 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 31
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 24
- 150000004820 halides Chemical group 0.000 claims description 24
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 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 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 11
- 239000005711 Benzoic acid Substances 0.000 claims description 10
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 10
- 235000010233 benzoic acid Nutrition 0.000 claims description 10
- FJFCENCQWXKBSW-UHFFFAOYSA-N phenyl-(4-thiophen-2-ylphenyl)methanone Chemical compound C=1C=C(C=2SC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 FJFCENCQWXKBSW-UHFFFAOYSA-N 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 229920001519 homopolymer Polymers 0.000 claims description 6
- 238000012643 polycondensation polymerization Methods 0.000 claims description 6
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 5
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 5
- 238000011065 in-situ storage Methods 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical group ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims 2
- 244000028419 Styrax benzoin Species 0.000 claims 1
- 235000000126 Styrax benzoin Nutrition 0.000 claims 1
- 235000008411 Sumatra benzointree Nutrition 0.000 claims 1
- 229960002130 benzoin Drugs 0.000 claims 1
- 235000019382 gum benzoic Nutrition 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000012039 electrophile Substances 0.000 description 19
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 18
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 18
- 239000003607 modifier Substances 0.000 description 17
- 229910015900 BF3 Inorganic materials 0.000 description 10
- 239000012038 nucleophile Substances 0.000 description 10
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 9
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 150000002576 ketones Chemical class 0.000 description 7
- 238000010791 quenching Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000005917 acylation reaction Methods 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 230000000171 quenching effect Effects 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- -1 aromatic sulfone Chemical class 0.000 description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 5
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical group ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 4
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- ZSBDGXGICLIJGD-UHFFFAOYSA-N 4-phenoxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-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
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- BSILAEQTGTZMIW-UHFFFAOYSA-N bis(4-phenoxyphenyl)methanone Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1C(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 BSILAEQTGTZMIW-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000004581 coalescence Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000002939 deleterious effect Effects 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 description 2
- PSCMQHVBLHHWTO-UHFFFAOYSA-K indium(iii) chloride Chemical compound Cl[In](Cl)Cl PSCMQHVBLHHWTO-UHFFFAOYSA-K 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229920000090 poly(aryl ether) Polymers 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CFTSORNHIUMCGF-UHFFFAOYSA-N (1,1,1,3,3,3-hexafluoro-2-phenylpropan-2-yl)benzene Chemical compound C=1C=CC=CC=1C(C(F)(F)F)(C(F)(F)F)C1=CC=CC=C1 CFTSORNHIUMCGF-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- PYIFQWWZCFQJQJ-UHFFFAOYSA-N 1-benzhydryl-4-nitrobenzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 PYIFQWWZCFQJQJ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- DABOOAVTBIRGHP-UHFFFAOYSA-N 1-phenoxynaphthalene Chemical compound C=1C=CC2=CC=CC=C2C=1OC1=CC=CC=C1 DABOOAVTBIRGHP-UHFFFAOYSA-N 0.000 description 1
- VUJPBQLLLURKBZ-UHFFFAOYSA-N 2-chlorobenzene-1,4-disulfonyl chloride Chemical compound ClC1=CC(S(Cl)(=O)=O)=CC=C1S(Cl)(=O)=O VUJPBQLLLURKBZ-UHFFFAOYSA-N 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
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- 238000010420 art technique Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- ALIQZUMMPOYCIS-UHFFFAOYSA-N benzene-1,3-disulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC(S(Cl)(=O)=O)=C1 ALIQZUMMPOYCIS-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
- 230000001588 bifunctional effect Effects 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 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
- 238000001035 drying Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- NFBOHOGPQUYFRF-UHFFFAOYSA-N oxanthrene Chemical compound C1=CC=C2OC3=CC=CC=C3OC2=C1 NFBOHOGPQUYFRF-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920002493 poly(chlorotrifluoroethylene) Polymers 0.000 description 1
- 239000005023 polychlorotrifluoroethylene (PCTFE) polymer Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920005547 polycyclic aromatic hydrocarbon Polymers 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 238000007868 post-polymerization treatment Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 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
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyethers (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62988775A | 1975-11-07 | 1975-11-07 | |
| US629887 | 1975-11-07 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14502487A Division JPS6354429A (ja) | 1975-11-07 | 1987-06-09 | ケトンおよびスルホン重合体の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01245019A JPH01245019A (ja) | 1989-09-29 |
| JPH0428732B2 true JPH0428732B2 (fr) | 1992-05-15 |
Family
ID=24524906
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13313476A Granted JPS5284300A (en) | 1975-11-07 | 1976-11-05 | Ketone and sulfone polymer |
| JP14502487A Granted JPS6354429A (ja) | 1975-11-07 | 1987-06-09 | ケトンおよびスルホン重合体の製造方法 |
| JP30870788A Granted JPH01245019A (ja) | 1975-11-07 | 1988-12-06 | 重合体の製法 |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13313476A Granted JPS5284300A (en) | 1975-11-07 | 1976-11-05 | Ketone and sulfone polymer |
| JP14502487A Granted JPS6354429A (ja) | 1975-11-07 | 1987-06-09 | ケトンおよびスルホン重合体の製造方法 |
Country Status (5)
| Country | Link |
|---|---|
| JP (3) | JPS5284300A (fr) |
| CA (1) | CA1112393A (fr) |
| DE (1) | DE2650943A1 (fr) |
| FR (1) | FR2330712A1 (fr) |
| GB (1) | GB1567190A (fr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1112393A (fr) * | 1975-11-07 | 1981-11-10 | Klaus J. Dahl | Polymeres contenant des cetones et des sulfones |
| DE2730128C3 (de) * | 1976-07-08 | 1982-04-29 | Imperial Chemical Industries Ltd., London | Aromatische Polyäthersulfone und-ketone und deren Copolymere und Verfahren zu deren Herstellung |
| US4361693A (en) * | 1981-07-08 | 1982-11-30 | Raychem Corporation | Preparation of poly(arylene ketones) using thio- and dithiocarbonic acid derivatives |
| JPH0680113B2 (ja) * | 1983-03-31 | 1994-10-12 | レイケム・コーポレイション | 芳香族ポリマ−の製法 |
| ES8700677A1 (es) * | 1984-10-11 | 1986-11-16 | Raychem Corp | Metodo para la preparacion de un oligomero de arileno cetonao arileno sulfona |
| DE4424042A1 (de) | 1994-07-11 | 1996-01-18 | Basf Ag | Schwefeloxide und deren Halogenderivate als elektrophiles Endgruppenverschlußreagens bei der elektrophilen Synthese von Polyaryletherketonen |
| GB201409127D0 (en) * | 2014-05-22 | 2014-07-09 | Ketonex Ltd | Method |
| CN115010926B (zh) * | 2022-07-05 | 2023-06-20 | 中国科学院长春应用化学研究所 | 一种聚砜树脂及其制备方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5039399A (fr) * | 1973-07-12 | 1975-04-11 | ||
| JPS6354429A (ja) * | 1975-11-07 | 1988-03-08 | レイケム、コ−ポレ−ション | ケトンおよびスルホン重合体の製造方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2266022C2 (fr) * | 1971-02-16 | 1987-11-19 | Raychem Corp., Menlo Park, Calif., Us | |
| US3914298A (en) * | 1971-02-16 | 1975-10-21 | Raychem Corp | Biphenylyloxybenzoyl halides |
| GB1541568A (en) * | 1975-08-20 | 1979-03-07 | Ici Ltd | Aromatic polymers |
| DK158532C (da) * | 1987-07-14 | 1990-10-29 | Niro Atomizer As | Toerreapparat, der arbejder med fluid bed, og lejeplade dertil |
-
1976
- 1976-11-01 CA CA264,516A patent/CA1112393A/fr not_active Expired
- 1976-11-05 JP JP13313476A patent/JPS5284300A/ja active Granted
- 1976-11-05 GB GB4617376A patent/GB1567190A/en not_active Expired
- 1976-11-05 FR FR7633454A patent/FR2330712A1/fr active Granted
- 1976-11-08 DE DE19762650943 patent/DE2650943A1/de active Granted
-
1987
- 1987-06-09 JP JP14502487A patent/JPS6354429A/ja active Granted
-
1988
- 1988-12-06 JP JP30870788A patent/JPH01245019A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5039399A (fr) * | 1973-07-12 | 1975-04-11 | ||
| JPS6354429A (ja) * | 1975-11-07 | 1988-03-08 | レイケム、コ−ポレ−ション | ケトンおよびスルホン重合体の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1567190A (en) | 1980-05-14 |
| DE2650943A1 (de) | 1977-05-12 |
| JPS6354429A (ja) | 1988-03-08 |
| JPH01245019A (ja) | 1989-09-29 |
| DE2650943C2 (fr) | 1987-09-10 |
| JPS5284300A (en) | 1977-07-13 |
| FR2330712A1 (fr) | 1977-06-03 |
| CA1112393A (fr) | 1981-11-10 |
| JPS6260411B2 (fr) | 1987-12-16 |
| JPH0133487B2 (fr) | 1989-07-13 |
| FR2330712B1 (fr) | 1983-05-27 |
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