CA1254347A - Polymeres et alliages a base de polyarylates derives de bis(hydroxyphenyl)fluorene - Google Patents

Polymeres et alliages a base de polyarylates derives de bis(hydroxyphenyl)fluorene

Info

Publication number: CA1254347A
Authority: CA; Canada
Prior art keywords: bis; hydroxyphenyl; fluorene; molar ratio; polyarylate
Prior art date: 1986-08-05
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

Application number

CA000515293A

Other languages

English (en)

Inventor

Phillip H. Parker

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Chevron USA Inc

Original Assignee

Chevron Research and Technology Co

Priority date (The priority date 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 date listed.)

1986-08-05

Filing date

1986-08-05

Publication date

1989-05-16

1986-08-05 Application filed by Chevron Research and Technology Co filed Critical Chevron Research and Technology Co

1986-08-05 Priority to CA000515293A priority Critical patent/CA1254347A/fr

1989-05-16 Application granted granted Critical

1989-05-16 Publication of CA1254347A publication Critical patent/CA1254347A/fr

Status Expired legal-status Critical Current

Links

229920001230 polyarylate Polymers 0.000 title claims abstract description 56
GUJZISPOCRVAMW-UHFFFAOYSA-N 2-[1-(2-hydroxyphenyl)-9h-fluoren-2-yl]phenol Chemical compound OC1=CC=CC=C1C1=CC=C(C=2C(=CC=CC=2)C2)C2=C1C1=CC=CC=C1O GUJZISPOCRVAMW-UHFFFAOYSA-N 0.000 title claims abstract description 28
239000000956 alloy Substances 0.000 title claims abstract description 21
229910045601 alloy Inorganic materials 0.000 title claims abstract description 21
229920000642 polymer Polymers 0.000 title abstract description 30
239000000203 mixture Substances 0.000 claims abstract description 85
229930185605 Bisphenol Natural products 0.000 claims abstract description 54
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 abstract description 37
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 32
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims abstract description 22
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 16
239000004793 Polystyrene Substances 0.000 claims abstract description 15
229920002223 polystyrene Polymers 0.000 claims abstract description 14
239000002952 polymeric resin Substances 0.000 claims abstract description 5
229920003002 synthetic resin Polymers 0.000 claims abstract description 5
-1 bis(hydroxyphenyl)fluorene compound Chemical class 0.000 claims description 30
125000004432 carbon atom Chemical group C* 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
229920001577 copolymer Polymers 0.000 claims description 17
150000002431 hydrogen Chemical class 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
238000006116 polymerization reaction Methods 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
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 abstract description 19
NSHCRPPLVZTBPG-UHFFFAOYSA-N anthracene;phenol Chemical class OC1=CC=CC=C1.OC1=CC=CC=C1.C1=CC=CC2=CC3=CC=CC=C3C=C21 NSHCRPPLVZTBPG-UHFFFAOYSA-N 0.000 abstract description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 12
238000000034 method Methods 0.000 description 11
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 10
239000003054 catalyst Substances 0.000 description 10
239000000243 solution Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 9
239000003960 organic solvent Substances 0.000 description 9
150000001875 compounds Chemical class 0.000 description 7
NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 6
SNPPMOSOWNHABX-UHFFFAOYSA-N 4-[9-(4-hydroxy-3,5-dimethylphenyl)fluoren-9-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C)C(O)=C(C)C=2)=C1 SNPPMOSOWNHABX-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
229920001519 homopolymer Polymers 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000012670 alkaline solution Substances 0.000 description 5
125000004464 hydroxyphenyl group Chemical group 0.000 description 5
238000000465 moulding Methods 0.000 description 5
150000002989 phenols Chemical class 0.000 description 5
229920000728 polyester Polymers 0.000 description 5
239000000047 product Substances 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
238000005727 Friedel-Crafts reaction Methods 0.000 description 4
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
239000003513 alkali Substances 0.000 description 4
125000003118 aryl group Chemical group 0.000 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 description 4
150000005690 diesters Chemical class 0.000 description 4
230000009477 glass transition Effects 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
238000003756 stirring Methods 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
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
238000012696 Interfacial polycondensation Methods 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 3
239000003963 antioxidant agent Substances 0.000 description 3
MGIAHHJRDZCTHG-UHFFFAOYSA-N benzene-1,3-dicarboxylic acid;terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1.OC(=O)C1=CC=CC(C(O)=O)=C1 MGIAHHJRDZCTHG-UHFFFAOYSA-N 0.000 description 3
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 3
230000015556 catabolic process Effects 0.000 description 3
238000000113 differential scanning calorimetry Methods 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
238000010528 free radical solution polymerization reaction Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 3
229920000515 polycarbonate Polymers 0.000 description 3
239000004417 polycarbonate Substances 0.000 description 3
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
238000000967 suction filtration Methods 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
KKRWLAXGEZRCIW-UHFFFAOYSA-N 2-[1-(2-hydroxyphenyl)-9h-fluoren-2-yl]phenol;phenol Chemical compound OC1=CC=CC=C1.OC1=CC=CC=C1.OC1=CC=CC=C1C1=CC=C(C=2C(=CC=CC=2)C2)C2=C1C1=CC=CC=C1O KKRWLAXGEZRCIW-UHFFFAOYSA-N 0.000 description 2
ORCFBNUIUVJEJA-UHFFFAOYSA-N 5,6-bis(2-hydroxyphenyl)-2h-anthracen-1-one Chemical compound OC1=CC=CC=C1C1=CC=C(C=C2C(C=CCC2=O)=C2)C2=C1C1=CC=CC=C1O ORCFBNUIUVJEJA-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
238000005452 bending Methods 0.000 description 2
LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000001125 extrusion Methods 0.000 description 2
239000000835 fiber Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
238000001746 injection moulding Methods 0.000 description 2
239000010410 layer Substances 0.000 description 2
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000012046 mixed solvent Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
235000021317 phosphate Nutrition 0.000 description 2
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
239000004408 titanium dioxide Substances 0.000 description 2
HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
BEBDHNOMRSGJCE-UHFFFAOYSA-N (2-hydroxyphenyl)-dimethylsulfanium;chloride Chemical compound [Cl-].C[S+](C)C1=CC=CC=C1O BEBDHNOMRSGJCE-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
NGQTUWCDHLILAX-UHFFFAOYSA-N 2,2-dichloroethylbenzene Chemical compound ClC(Cl)CC1=CC=CC=C1 NGQTUWCDHLILAX-UHFFFAOYSA-N 0.000 description 1
KWWMNLQDGJZHSK-UHFFFAOYSA-N 4-anthracen-1-ylphenol Chemical compound C1=CC(O)=CC=C1C1=CC=CC2=CC3=CC=CC=C3C=C12 KWWMNLQDGJZHSK-UHFFFAOYSA-N 0.000 description 1
YJCZGDLWSLXOQL-UHFFFAOYSA-N 4-phenyl-2h-benzotriazol-5-amine Chemical compound NC1=CC=C2NN=NC2=C1C1=CC=CC=C1 YJCZGDLWSLXOQL-UHFFFAOYSA-N 0.000 description 1
LSTBDYVWQHHYHU-UHFFFAOYSA-N 9,9-dichlorofluorene Chemical compound C1=CC=C2C(Cl)(Cl)C3=CC=CC=C3C2=C1 LSTBDYVWQHHYHU-UHFFFAOYSA-N 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
238000012695 Interfacial polymerization Methods 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
229920004313 LEXAN™ RESIN 141 Polymers 0.000 description 1
101100109871 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) aro-8 gene Proteins 0.000 description 1
YHYITPYNGUZSNF-UHFFFAOYSA-N O=C(C1=CC(C(Cl)=O)=CC=C1)Cl.Cl.Cl Chemical compound O=C(C1=CC(C(Cl)=O)=CC=C1)Cl.Cl.Cl YHYITPYNGUZSNF-UHFFFAOYSA-N 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000003868 ammonium compounds Chemical group 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N anhydrous trimethylamine Natural products CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
150000004056 anthraquinones Chemical class 0.000 description 1
QEZIKGQWAWNWIR-UHFFFAOYSA-N antimony(3+) antimony(5+) oxygen(2-) Chemical compound [O--].[O--].[O--].[O--].[Sb+3].[Sb+5] QEZIKGQWAWNWIR-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
239000002585 base Substances 0.000 description 1
PYGSFJHAOJNADQ-UHFFFAOYSA-N benzene-1,3-dicarboxylic acid;phenol;terephthalic acid Chemical compound OC1=CC=CC=C1.OC1=CC=CC=C1.OC(=O)C1=CC=C(C(O)=O)C=C1.OC(=O)C1=CC=CC(C(O)=O)=C1 PYGSFJHAOJNADQ-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
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
239000012964 benzotriazole Substances 0.000 description 1
KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 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
FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
229950005499 carbon tetrachloride Drugs 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000005336 cracking Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
LERGDXJITDVDBZ-UHFFFAOYSA-N dioctyl benzene-1,3-dicarboxylate Chemical compound CCCCCCCCOC(=O)C1=CC=CC(C(=O)OCCCCCCCC)=C1 LERGDXJITDVDBZ-UHFFFAOYSA-N 0.000 description 1
OEIWPNWSDYFMIL-UHFFFAOYSA-N dioctyl benzene-1,4-dicarboxylate Chemical compound CCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC)C=C1 OEIWPNWSDYFMIL-UHFFFAOYSA-N 0.000 description 1
FHESUNXRPBHDQM-UHFFFAOYSA-N diphenyl benzene-1,3-dicarboxylate Chemical compound C=1C=CC(C(=O)OC=2C=CC=CC=2)=CC=1C(=O)OC1=CC=CC=C1 FHESUNXRPBHDQM-UHFFFAOYSA-N 0.000 description 1
HPGJOUYGWKFYQW-UHFFFAOYSA-N diphenyl benzene-1,4-dicarboxylate Chemical compound C=1C=C(C(=O)OC=2C=CC=CC=2)C=CC=1C(=O)OC1=CC=CC=C1 HPGJOUYGWKFYQW-UHFFFAOYSA-N 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
229920006351 engineering plastic Polymers 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
150000002531 isophthalic acids Chemical class 0.000 description 1
229910000464 lead oxide Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
150000002763 monocarboxylic acids Chemical class 0.000 description 1
YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
FFQLQBKXOPDGSG-UHFFFAOYSA-N octadecyl benzenesulfonate Chemical compound CCCCCCCCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 FFQLQBKXOPDGSG-UHFFFAOYSA-N 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
235000010292 orthophenyl phenol Nutrition 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 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
NKTOLZVEWDHZMU-UHFFFAOYSA-N p-cumyl phenol Natural products CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 1
239000008188 pellet Substances 0.000 description 1
238000005453 pelletization Methods 0.000 description 1
150000002976 peresters Chemical group 0.000 description 1
239000012071 phase Substances 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
239000006069 physical mixture Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000412 polyarylene Polymers 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
229920000139 polyethylene terephthalate Polymers 0.000 description 1
239000005020 polyethylene terephthalate Substances 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000000843 powder Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
229960005335 propanol Drugs 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
150000004023 quaternary phosphonium compounds Chemical class 0.000 description 1
238000011084 recovery Methods 0.000 description 1
239000011342 resin composition Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
150000004026 tertiary sulfonium compounds Chemical class 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000003609 titanium compounds Chemical class 0.000 description 1
STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
229940086542 triethylamine Drugs 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-O trimethylammonium Chemical compound C[NH+](C)C GETQZCLCWQTVFV-UHFFFAOYSA-O 0.000 description 1
QOQNJVLFFRMJTQ-UHFFFAOYSA-N trioctyl phosphite Chemical compound CCCCCCCCOP(OCCCCCCCC)OCCCCCCCC QOQNJVLFFRMJTQ-UHFFFAOYSA-N 0.000 description 1
IZYFBZDLXRHRLF-UHFFFAOYSA-N tritylphosphane;hydroiodide Chemical compound [I-].C=1C=CC=CC=1C(C=1C=CC=CC=1)([PH3+])C1=CC=CC=C1 IZYFBZDLXRHRLF-UHFFFAOYSA-N 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1

Landscapes

Polyesters Or Polycarbonates (AREA)

CA000515293A 1986-08-05 1986-08-05 Polymeres et alliages a base de polyarylates derives de bis(hydroxyphenyl)fluorene Expired CA1254347A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000515293A CA1254347A (fr)	1986-08-05	1986-08-05	Polymeres et alliages a base de polyarylates derives de bis(hydroxyphenyl)fluorene

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000515293A CA1254347A (fr)	1986-08-05	1986-08-05	Polymeres et alliages a base de polyarylates derives de bis(hydroxyphenyl)fluorene

Publications (1)

Publication Number	Publication Date
CA1254347A true CA1254347A (fr)	1989-05-16

Family

ID=4133678

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000515293A Expired CA1254347A (fr)	1986-08-05	1986-08-05	Polymeres et alliages a base de polyarylates derives de bis(hydroxyphenyl)fluorene

Country Status (1)

Country	Link
CA (1)	CA1254347A (fr)

1986
- 1986-08-05 CA CA000515293A patent/CA1254347A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2006-08-05	MKEX	Expiry

Publication	Publication Date	Title
US4584335A (en)	1986-04-22	5-keto-bis(hydroxyphenyl)anthracene polyarylate copolymers and alloys
US4612350A (en)	1986-09-16	Bis(hydroxyphenyl)fluorene polyarylate polymers and alloys
US3160602A (en)	1964-12-08	Process of producing aromatic polyesters
CA1173998A (fr)	1984-09-04	Procede d'obtention de carbonates de polyesters aromatiques et l'emploi pour la production d'articles moules par injection, de pellicules et d'enduits
US3946091A (en)	1976-03-23	Aromatic co-polyester articles showing reduced crazing
EP0036629B1 (fr)	1984-08-08	Polyestercarbonate traitable en fusion possédant une température élevée de transition vitreuse
EP0258504B1 (fr)	1991-11-06	Polymères de polyarylate de fluorène et compositions d'alliage à partir de ces polymères
KR0158882B1 (ko)	1999-01-15	1,1-비스-(4-하이드록시페닐)-알킬사이클로알칸을 기본으로 하는 폴리에스테르 및 폴리에스테르-카보네이트
US4342862A (en)	1982-08-03	Polyesters of trans-1,4-cyclohexanedicarboxylic acid and 2-phenylhydroquinone and modifications thereof
US4097431A (en)	1978-06-27	Aromatic copolyester composition
US4123454A (en)	1978-10-31	Thermoplastic copolyesters
JPH023807B2 (fr)	1990-01-25
US3720721A (en)	1973-03-13	Halogenated biphenols and methods for preparing the same
US3160603A (en)	1964-12-08	Wholly aromatic poly-p-phenylene chloroisophthalates
EP0279091B1 (fr)	1992-05-27	Polymères de polyarylate à base de phénolphtaléine, et composition d'alliage à partir de ceux-ci
CA1264891A (fr)	1990-01-23	Copolymeres et alliages a base de 5-ceto-bis (hydroxyphenyl)anthracene et de polyarylate
US4731433A (en)	1988-03-15	Aromatic copolyester derived from aromatic dicarboxylic acid component and aromatic diol component
US4064196A (en)	1977-12-20	Flame-retardant resin compositions
JPS629130B2 (fr)	1987-02-26
CA1274043A (fr)	1990-09-11	Polymeres de polyarylate de phenolphtaleine et melanges de ceux-ci
US4412057A (en)	1983-10-25	Process for manufacturing aromatic polyesters
EP0056149B1 (fr)	1986-06-11	Procédé de préparation de polyesters aromatiques
US3438938A (en)	1969-04-15	Polyester resins and preparation thereof
US4031063A (en)	1977-06-21	Polyester resin compositions
US3449295A (en)	1969-06-10	High molecular weight linear copolyesters of bisphenols and mixtures of ortho-phthalic and iso- and/or terephthalic acids