JPS6132332B2 - - Google Patents

Info

Publication number

JPS6132332B2

JPS6132332B2 JP3626277A JP3626277A JPS6132332B2 JP S6132332 B2 JPS6132332 B2 JP S6132332B2 JP 3626277 A JP3626277 A JP 3626277A JP 3626277 A JP3626277 A JP 3626277A JP S6132332 B2 JPS6132332 B2 JP S6132332B2

Authority

JP

Japan

Prior art keywords

polymer

bpa

bisphenol

pyridine

carbonate

Prior art date

1976-04-02

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

Links

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• 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 claims description 174
• 229920000642 polymer Polymers 0.000 claims description 97
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 84
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 82
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 41
• LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 claims description 40
• 229920001577 copolymer Polymers 0.000 claims description 39
• KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 27
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 24
• 229920000728 polyester Polymers 0.000 claims description 23
• YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 20
• 238000006243 chemical reaction Methods 0.000 claims description 19
• 239000011541 reaction mixture Substances 0.000 claims description 18
• 239000002904 solvent Substances 0.000 claims description 15
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
• 239000012429 reaction media Substances 0.000 claims description 12
• 238000012360 testing method Methods 0.000 claims description 12
• 238000000034 method Methods 0.000 claims description 11
• KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims description 11
• 229920000515 polycarbonate Polymers 0.000 claims description 10
• 239000004417 polycarbonate Substances 0.000 claims description 10
• 230000015572 biosynthetic process Effects 0.000 claims description 7
• 239000003795 chemical substances by application Substances 0.000 claims description 7
• 229910052757 nitrogen Inorganic materials 0.000 claims description 6
• 238000004260 weight control Methods 0.000 claims description 6
• 230000009477 glass transition Effects 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 239000003960 organic solvent Substances 0.000 claims description 5
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
• -1 bisphenol A diester Chemical class 0.000 claims description 4
• 230000006835 compression Effects 0.000 claims description 4
• 238000007906 compression Methods 0.000 claims description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
• 150000002989 phenols Chemical class 0.000 claims description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
• 238000000113 differential scanning calorimetry Methods 0.000 claims description 3
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
• 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
• 230000008859 change Effects 0.000 claims description 2
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims 2
• XGIAHMUOCFHQTI-UHFFFAOYSA-N Cl.Cl.Cl.Cl.CC Chemical compound Cl.Cl.Cl.Cl.CC XGIAHMUOCFHQTI-UHFFFAOYSA-N 0.000 claims 1
• 229910052786 argon Inorganic materials 0.000 claims 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 26
• 239000000243 solution Substances 0.000 description 24
• 239000000047 product Substances 0.000 description 23
• 239000000376 reactant Substances 0.000 description 13
• 239000000203 mixture Substances 0.000 description 12
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
• 230000000052 comparative effect Effects 0.000 description 9
• 150000002148 esters Chemical class 0.000 description 8
• 238000000465 moulding Methods 0.000 description 8
• 239000007787 solid Substances 0.000 description 7
• 238000010521 absorption reaction Methods 0.000 description 6
• 238000005299 abrasion Methods 0.000 description 5
• 238000004458 analytical method Methods 0.000 description 5
• 238000005119 centrifugation Methods 0.000 description 5
• 150000005690 diesters Chemical class 0.000 description 5
• 239000000178 monomer Substances 0.000 description 5
• 238000002360 preparation method Methods 0.000 description 5
• 238000003756 stirring Methods 0.000 description 5
• 238000005406 washing Methods 0.000 description 5
• QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 4
• 239000002253 acid Substances 0.000 description 4
• 229920005603 alternating copolymer Polymers 0.000 description 4
• 238000011088 calibration curve Methods 0.000 description 4
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
• 238000002474 experimental method Methods 0.000 description 4
• QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
• 239000007788 liquid Substances 0.000 description 4
• 238000005259 measurement Methods 0.000 description 4
• 238000001556 precipitation Methods 0.000 description 4
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• 238000013019 agitation Methods 0.000 description 3
• AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical group OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 3
• 238000001816 cooling Methods 0.000 description 3
• 238000010586 diagram Methods 0.000 description 3
• 238000001125 extrusion Methods 0.000 description 3
• 239000011521 glass Substances 0.000 description 3
• 238000002844 melting Methods 0.000 description 3
• 230000008018 melting Effects 0.000 description 3
• 239000002245 particle Substances 0.000 description 3
• 238000000746 purification Methods 0.000 description 3
• 239000002994 raw material Substances 0.000 description 3
• 238000000926 separation method Methods 0.000 description 3
• 239000000126 substance Substances 0.000 description 3
• WEHZNZTWKUYVIY-UHFFFAOYSA-N 3-oxabicyclo[3.2.2]nona-1(7),5,8-triene-2,4-dione Chemical compound O=C1OC(=O)C2=CC=C1C=C2 WEHZNZTWKUYVIY-UHFFFAOYSA-N 0.000 description 2
• OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 2
• XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
• CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical compound ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-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
• 150000007513 acids Chemical class 0.000 description 2
• 230000009471 action Effects 0.000 description 2
• WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
• 150000008064 anhydrides Chemical class 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
• 150000007942 carboxylates Chemical class 0.000 description 2
• 230000015556 catabolic process Effects 0.000 description 2
• 238000006731 degradation reaction Methods 0.000 description 2
• 238000004821 distillation Methods 0.000 description 2
• 230000000694 effects Effects 0.000 description 2
• 230000001747 exhibiting effect Effects 0.000 description 2
• 230000002349 favourable effect Effects 0.000 description 2
• 238000010438 heat treatment Methods 0.000 description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
• 239000012535 impurity Substances 0.000 description 2
• 239000011261 inert gas Substances 0.000 description 2
• 238000002329 infrared spectrum Methods 0.000 description 2
• 238000001746 injection moulding Methods 0.000 description 2
• 238000006116 polymerization reaction Methods 0.000 description 2
• 239000000843 powder Substances 0.000 description 2
• 239000002244 precipitate Substances 0.000 description 2
• 239000002243 precursor Substances 0.000 description 2
• AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
• 239000011877 solvent mixture Substances 0.000 description 2
• 238000001228 spectrum Methods 0.000 description 2
• 229950011008 tetrachloroethylene Drugs 0.000 description 2
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
• 230000004580 weight loss Effects 0.000 description 2
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
• ZNJRONVKWRHYBF-UHFFFAOYSA-N 2-[2-[2-(1-azatricyclo[7.3.1.05,13]trideca-5,7,9(13)-trien-7-yl)ethenyl]-6-methylpyran-4-ylidene]propanedinitrile Chemical group O1C(C)=CC(=C(C#N)C#N)C=C1C=CC1=CC(CCCN2CCC3)=C2C3=C1 ZNJRONVKWRHYBF-UHFFFAOYSA-N 0.000 description 1
• WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
• 229910000619 316 stainless steel Inorganic materials 0.000 description 1
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
• 101710134784 Agnoprotein Proteins 0.000 description 1
• DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
• 229910002808 Si–O–Si Inorganic materials 0.000 description 1
• 239000001361 adipic acid Substances 0.000 description 1
• 235000011037 adipic acid Nutrition 0.000 description 1
• PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 1
• 230000002411 adverse Effects 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
• 238000013459 approach Methods 0.000 description 1
• 239000012300 argon atmosphere Substances 0.000 description 1
• 230000005540 biological transmission Effects 0.000 description 1
• 229920000402 bisphenol A polycarbonate polymer Polymers 0.000 description 1
• 229910052799 carbon Inorganic materials 0.000 description 1
• 125000005587 carbonate group Chemical group 0.000 description 1
• 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
• 150000001805 chlorine compounds Chemical class 0.000 description 1
• 238000004587 chromatography analysis Methods 0.000 description 1
• 239000011248 coating agent Substances 0.000 description 1
• 238000000576 coating method Methods 0.000 description 1
• 150000001875 compounds Chemical class 0.000 description 1
• 238000000748 compression moulding Methods 0.000 description 1
• 238000009833 condensation Methods 0.000 description 1
• 230000005494 condensation Effects 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• 239000013078 crystal Substances 0.000 description 1
• 230000007423 decrease Effects 0.000 description 1
• 230000006866 deterioration Effects 0.000 description 1
• 238000002845 discoloration Methods 0.000 description 1
• 239000006185 dispersion Substances 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• 239000012153 distilled water Substances 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 238000004817 gas chromatography Methods 0.000 description 1
• 239000003502 gasoline Substances 0.000 description 1
• FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
• DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
• 230000002779 inactivation Effects 0.000 description 1
• 239000012442 inert solvent Substances 0.000 description 1
• 238000002347 injection Methods 0.000 description 1
• 239000007924 injection Substances 0.000 description 1
• 230000003993 interaction Effects 0.000 description 1
• 238000011835 investigation Methods 0.000 description 1
• 238000002955 isolation Methods 0.000 description 1
• 238000011005 laboratory method Methods 0.000 description 1
• 238000002789 length control Methods 0.000 description 1
• 239000007791 liquid phase Substances 0.000 description 1
• 238000011068 loading method Methods 0.000 description 1
• 238000000691 measurement method Methods 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• NZZGQZMNFCTNAM-UHFFFAOYSA-N naphthalene-2,6-dicarbonyl chloride Chemical compound C1=C(C(Cl)=O)C=CC2=CC(C(=O)Cl)=CC=C21 NZZGQZMNFCTNAM-UHFFFAOYSA-N 0.000 description 1
• 239000012299 nitrogen atmosphere Substances 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 239000012074 organic phase Substances 0.000 description 1
• QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 description 1
• 230000000704 physical effect Effects 0.000 description 1
• 230000008569 process Effects 0.000 description 1
• 230000002035 prolonged effect Effects 0.000 description 1
• 238000010926 purge Methods 0.000 description 1
• 238000010791 quenching Methods 0.000 description 1
• 230000000171 quenching effect Effects 0.000 description 1
• 238000011084 recovery Methods 0.000 description 1
• 238000003303 reheating Methods 0.000 description 1
• 238000011160 research Methods 0.000 description 1
• 238000006748 scratching Methods 0.000 description 1
• 230000002393 scratching effect Effects 0.000 description 1
• 239000000741 silica gel Substances 0.000 description 1
• 229910002027 silica gel Inorganic materials 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 239000003381 stabilizer Substances 0.000 description 1
• 229910001220 stainless steel Inorganic materials 0.000 description 1
• 239000010935 stainless steel Substances 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• 238000003860 storage Methods 0.000 description 1
• 239000000758 substrate Substances 0.000 description 1
• 238000009864 tensile test Methods 0.000 description 1
• 238000012546 transfer Methods 0.000 description 1
• 238000001721 transfer moulding Methods 0.000 description 1

Cited By (1)