CA1054745A - Polymeres de type polyester a microstructure ordonnee, a poids moleculaire eleve et a faible viscosite - Google Patents

Polymeres de type polyester a microstructure ordonnee, a poids moleculaire eleve et a faible viscosite

Info

Publication number: CA1054745A
Authority: CA; Canada
Prior art keywords: glycol; bisphenol; polyester; chloride; hydroxyl
Prior art date: 1976-01-21
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

CA243977A

Other languages

English (en)

Inventor

Joseph A. Pawlak

Anthony L. Lemper

Victor A. Pattison

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.)

Occidental Chemical Corp

Original Assignee

Hooker Chemicals and Plastics Corp

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.)

1976-01-21

Filing date

1976-01-21

Publication date

1979-05-15

1976-01-21 Application filed by Hooker Chemicals and Plastics Corp filed Critical Hooker Chemicals and Plastics Corp

1976-01-21 Priority to CA243977A priority Critical patent/CA1054745A/fr

1979-05-15 Application granted granted Critical

1979-05-15 Publication of CA1054745A publication Critical patent/CA1054745A/fr

Status Expired legal-status Critical Current

Links

229920000728 polyester Polymers 0.000 title claims abstract description 35
229920000642 polymer Polymers 0.000 title abstract description 34
238000000034 method Methods 0.000 claims abstract description 49
150000004820 halides Chemical class 0.000 claims abstract description 32
230000008569 process Effects 0.000 claims abstract description 27
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 22
125000003118 aryl group Chemical group 0.000 claims abstract description 13
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 45
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 32
229930185605 Bisphenol Natural products 0.000 claims description 24
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims description 23
-1 haloalkylene Chemical group 0.000 claims description 22
238000006243 chemical reaction Methods 0.000 claims description 21
239000000203 mixture Substances 0.000 claims description 20
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 17
LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical group ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 13
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 12
229940117969 neopentyl glycol Drugs 0.000 claims description 12
229940106691 bisphenol a Drugs 0.000 claims description 10
238000010528 free radical solution polymerization reaction Methods 0.000 claims description 10
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 8
239000003054 catalyst Substances 0.000 claims description 7
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 description 6
125000002947 alkylene group Chemical group 0.000 claims description 5
125000000732 arylene group Chemical group 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000002877 alkyl aryl group Chemical group 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000002993 cycloalkylene group Chemical group 0.000 claims description 3
125000001188 haloalkyl group Chemical group 0.000 claims description 3
125000003106 haloaryl group Chemical group 0.000 claims description 3
125000005347 halocycloalkyl group Chemical group 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 claims description 2
206010058155 Heart alternation Diseases 0.000 claims description 2
125000006492 halo alkyl aryl group Chemical group 0.000 claims description 2
239000004615 ingredient Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
229910052799 carbon Inorganic materials 0.000 claims 1
239000002253 acid Substances 0.000 abstract description 8
238000006068 polycondensation reaction Methods 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
239000000243 solution Substances 0.000 description 35
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
238000007792 addition Methods 0.000 description 27
229940073584 methylene chloride Drugs 0.000 description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
239000000306 component Substances 0.000 description 18
229940086542 triethylamine Drugs 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 13
239000002904 solvent Substances 0.000 description 13
VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 11
239000000047 product Substances 0.000 description 11
239000012153 distilled water Substances 0.000 description 10
239000001294 propane Substances 0.000 description 10
239000000376 reactant Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
238000001556 precipitation Methods 0.000 description 5
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
238000010533 azeotropic distillation Methods 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
238000009833 condensation Methods 0.000 description 4
230000005494 condensation Effects 0.000 description 4
150000002009 diols Chemical class 0.000 description 4
238000001035 drying Methods 0.000 description 4
230000009477 glass transition Effects 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
230000009257 reactivity Effects 0.000 description 4
238000010992 reflux Methods 0.000 description 4
238000005406 washing Methods 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229920005603 alternating copolymer Polymers 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000004305 biphenyl Substances 0.000 description 3
150000001805 chlorine compounds Chemical class 0.000 description 3
238000000113 differential scanning calorimetry Methods 0.000 description 3
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
150000002334 glycols Chemical class 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
238000006116 polymerization reaction Methods 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
ZLYYJUJDFKGVKB-OWOJBTEDSA-N (e)-but-2-enedioyl dichloride Chemical compound ClC(=O)\C=C\C(Cl)=O ZLYYJUJDFKGVKB-OWOJBTEDSA-N 0.000 description 2
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
230000008901 benefit Effects 0.000 description 2
235000010290 biphenyl Nutrition 0.000 description 2
PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000001273 butane Substances 0.000 description 2
235000019437 butane-1,3-diol Nutrition 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
238000011088 calibration curve Methods 0.000 description 2
238000006482 condensation reaction Methods 0.000 description 2
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
239000000835 fiber Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000005227 gel permeation chromatography Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229920006158 high molecular weight polymer Polymers 0.000 description 2
125000001145 hydrido group Chemical group *[H] 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
239000000155 melt Substances 0.000 description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
229920001897 terpolymer Polymers 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
GVSYDCGFYSVNAX-UHFFFAOYSA-N 1,2-dihexylbenzene Chemical class CCCCCCC1=CC=CC=C1CCCCCC GVSYDCGFYSVNAX-UHFFFAOYSA-N 0.000 description 1
IPNQEKDRLAFQKQ-UHFFFAOYSA-N 1,2-dimethylcyclohexane-1,2-diol Chemical compound CC1(O)CCCCC1(C)O IPNQEKDRLAFQKQ-UHFFFAOYSA-N 0.000 description 1
IICHVFLQUNQPON-UHFFFAOYSA-N 1,2-dimethylcyclopentane-1,2-diol Chemical compound CC1(O)CCCC1(C)O IICHVFLQUNQPON-UHFFFAOYSA-N 0.000 description 1
229940058015 1,3-butylene glycol Drugs 0.000 description 1
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
PCMIWASLPQNSCD-UHFFFAOYSA-N 1-cyclohexyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C1CCCCC1 PCMIWASLPQNSCD-UHFFFAOYSA-N 0.000 description 1
ZAJYARZMPOEGLK-UHFFFAOYSA-N 1-ethyl-2-propan-2-ylbenzene Chemical compound CCC1=CC=CC=C1C(C)C ZAJYARZMPOEGLK-UHFFFAOYSA-N 0.000 description 1
KZFJKZOIPUWQJU-UHFFFAOYSA-N 1-hexyl-2-propan-2-ylbenzene Chemical compound CCCCCCC1=CC=CC=C1C(C)C KZFJKZOIPUWQJU-UHFFFAOYSA-N 0.000 description 1
JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 description 1
WIFDRXSVRSCMMY-UHFFFAOYSA-N 2,6-dichloro-4-[(3,5-dichloro-4-hydroxyphenyl)methyl]phenol Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1CC1=CC(Cl)=C(O)C(Cl)=C1 WIFDRXSVRSCMMY-UHFFFAOYSA-N 0.000 description 1
BLDLRWQLBOJPEB-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfanylphenol Chemical compound OC1=CC=CC=C1SC1=CC=CC=C1O BLDLRWQLBOJPEB-UHFFFAOYSA-N 0.000 description 1
RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 1
HYYFAYFMSHAWFA-UHFFFAOYSA-N 2-cyclohexylethylbenzene Chemical compound C1CCCCC1CCC1=CC=CC=C1 HYYFAYFMSHAWFA-UHFFFAOYSA-N 0.000 description 1
VNAWKNVDKFZFSU-UHFFFAOYSA-N 2-ethyl-2-methylpropane-1,3-diol Chemical compound CCC(C)(CO)CO VNAWKNVDKFZFSU-UHFFFAOYSA-N 0.000 description 1
JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
BZVMGPSXJDFUPI-UHFFFAOYSA-N 3-[2-(3-carboxyphenyl)propan-2-yl]benzoic acid Chemical compound C=1C=CC(C(O)=O)=CC=1C(C)(C)C1=CC=CC(C(O)=O)=C1 BZVMGPSXJDFUPI-UHFFFAOYSA-N 0.000 description 1
LAIMYEJOJSIPQW-UHFFFAOYSA-N 3-[3-(3-carboxyphenyl)heptan-3-yl]benzoic acid Chemical compound C=1C=CC(C(O)=O)=CC=1C(CC)(CCCC)C1=CC=CC(C(O)=O)=C1 LAIMYEJOJSIPQW-UHFFFAOYSA-N 0.000 description 1
XWEBTVZIZWEJOO-UHFFFAOYSA-N 3-chlorosulfonylbenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(S(Cl)(=O)=O)=C1 XWEBTVZIZWEJOO-UHFFFAOYSA-N 0.000 description 1
MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
WVDRSXGPQWNUBN-UHFFFAOYSA-N 4-(4-carboxyphenoxy)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CC=C(C(O)=O)C=C1 WVDRSXGPQWNUBN-UHFFFAOYSA-N 0.000 description 1
SQJQLYOMPSJVQS-UHFFFAOYSA-N 4-(4-carboxyphenyl)sulfonylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1S(=O)(=O)C1=CC=C(C(O)=O)C=C1 SQJQLYOMPSJVQS-UHFFFAOYSA-N 0.000 description 1
OTFAWEIFBPUXOH-UHFFFAOYSA-N 4-(4-chlorosulfonylphenyl)benzenesulfonyl chloride Chemical compound C1=CC(S(=O)(=O)Cl)=CC=C1C1=CC=C(S(Cl)(=O)=O)C=C1 OTFAWEIFBPUXOH-UHFFFAOYSA-N 0.000 description 1
RQCACQIALULDSK-UHFFFAOYSA-N 4-(4-hydroxyphenyl)sulfinylphenol Chemical compound C1=CC(O)=CC=C1S(=O)C1=CC=C(O)C=C1 RQCACQIALULDSK-UHFFFAOYSA-N 0.000 description 1
JGEQBQZIGJPCSP-UHFFFAOYSA-N 4-[(4-carboxyphenyl)-dichloromethyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(Cl)(Cl)C1=CC=C(C(O)=O)C=C1 JGEQBQZIGJPCSP-UHFFFAOYSA-N 0.000 description 1
VTDMBRAUHKUOON-UHFFFAOYSA-N 4-[(4-carboxyphenyl)methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CC1=CC=C(C(O)=O)C=C1 VTDMBRAUHKUOON-UHFFFAOYSA-N 0.000 description 1
MIFGCULLADMRTF-UHFFFAOYSA-N 4-[(4-hydroxy-3-methylphenyl)methyl]-2-methylphenol Chemical compound C1=C(O)C(C)=CC(CC=2C=C(C)C(O)=CC=2)=C1 MIFGCULLADMRTF-UHFFFAOYSA-N 0.000 description 1
BATCUENAARTUKW-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)-diphenylmethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BATCUENAARTUKW-UHFFFAOYSA-N 0.000 description 1
RSSGMIIGVQRGDS-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)-phenylmethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C1=CC=CC=C1 RSSGMIIGVQRGDS-UHFFFAOYSA-N 0.000 description 1
OLZBOWFKDWDPKA-UHFFFAOYSA-N 4-[1-(4-carboxyphenyl)ethyl]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1C(C)C1=CC=C(C(O)=O)C=C1 OLZBOWFKDWDPKA-UHFFFAOYSA-N 0.000 description 1
WJTQZEKXTKIYOW-UHFFFAOYSA-N 4-[2-(4-carboxyphenyl)-3-methylbutan-2-yl]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1C(C)(C(C)C)C1=CC=C(C(O)=O)C=C1 WJTQZEKXTKIYOW-UHFFFAOYSA-N 0.000 description 1
XZRZTOJUXFSPMZ-UHFFFAOYSA-N 4-[2-(4-carboxyphenyl)butan-2-yl]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1C(C)(CC)C1=CC=C(C(O)=O)C=C1 XZRZTOJUXFSPMZ-UHFFFAOYSA-N 0.000 description 1
PKECBVSFYYXVOV-UHFFFAOYSA-N 4-[2-(4-carboxyphenyl)pentan-2-yl]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1C(C)(CCC)C1=CC=C(C(O)=O)C=C1 PKECBVSFYYXVOV-UHFFFAOYSA-N 0.000 description 1
XKACUVXWRVMXOE-UHFFFAOYSA-N 4-[2-(4-carboxyphenyl)propan-2-yl]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1C(C)(C)C1=CC=C(C(O)=O)C=C1 XKACUVXWRVMXOE-UHFFFAOYSA-N 0.000 description 1
NNDRYYQCGFNWDX-UHFFFAOYSA-N 4-[3-(4-carboxyphenyl)heptan-3-yl]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1C(CC)(CCCC)C1=CC=C(C(O)=O)C=C1 NNDRYYQCGFNWDX-UHFFFAOYSA-N 0.000 description 1
YZYGDZRBLOLVDY-UHFFFAOYSA-N 4-[cyclohexyl-(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C1CCCCC1 YZYGDZRBLOLVDY-UHFFFAOYSA-N 0.000 description 1
JYJUMAFOXPQPAU-UHFFFAOYSA-N 4-chlorosulfonylbenzoyl chloride Chemical compound ClC(=O)C1=CC=C(S(Cl)(=O)=O)C=C1 JYJUMAFOXPQPAU-UHFFFAOYSA-N 0.000 description 1
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
LLQHSBBZNDXTIV-UHFFFAOYSA-N 6-[5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-4,5-dihydro-1,2-oxazol-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC1CC(=NO1)C1=CC2=C(NC(O2)=O)C=C1 LLQHSBBZNDXTIV-UHFFFAOYSA-N 0.000 description 1
229920001634 Copolyester Polymers 0.000 description 1
AQZGPSLYZOOYQP-UHFFFAOYSA-N Diisoamyl ether Chemical compound CC(C)CCOCCC(C)C AQZGPSLYZOOYQP-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
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OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
238000007707 calorimetry Methods 0.000 description 1
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MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
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238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000000498 cooling water Substances 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
WMPOZLHMGVKUEJ-UHFFFAOYSA-N decanedioyl dichloride Chemical compound ClC(=O)CCCCCCCCC(Cl)=O WMPOZLHMGVKUEJ-UHFFFAOYSA-N 0.000 description 1
230000007423 decrease Effects 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
150000005218 dimethyl ethers Chemical class 0.000 description 1
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
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239000011888 foil Substances 0.000 description 1
239000000727 fraction Substances 0.000 description 1
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125000005843 halogen group Chemical group 0.000 description 1
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IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
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TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 1
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238000012986 modification Methods 0.000 description 1
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NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
FJKUZZHKEDNPDN-UHFFFAOYSA-N naphthalene-2,7-disulfonyl chloride Chemical compound C1=CC(S(Cl)(=O)=O)=CC2=CC(S(=O)(=O)Cl)=CC=C21 FJKUZZHKEDNPDN-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
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GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000002103 osmometry Methods 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
BNIXVQGCZULYKV-UHFFFAOYSA-N pentachloroethane Chemical compound ClC(Cl)C(Cl)(Cl)Cl BNIXVQGCZULYKV-UHFFFAOYSA-N 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
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238000012545 processing Methods 0.000 description 1
TURAMGVWNUTQKH-UHFFFAOYSA-N propa-1,2-dien-1-one Chemical compound C=C=C=O TURAMGVWNUTQKH-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000012086 standard solution Substances 0.000 description 1
GFKSKVCFBACPGK-UHFFFAOYSA-N terephthalic acid;hydrochloride Chemical compound Cl.OC(=O)C1=CC=C(C(O)=O)C=C1 GFKSKVCFBACPGK-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
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ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Polyesters Or Polycarbonates (AREA)

CA243977A 1976-01-21 1976-01-21 Polymeres de type polyester a microstructure ordonnee, a poids moleculaire eleve et a faible viscosite Expired CA1054745A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA243977A CA1054745A (fr)	1976-01-21	1976-01-21	Polymeres de type polyester a microstructure ordonnee, a poids moleculaire eleve et a faible viscosite

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA243977A CA1054745A (fr)	1976-01-21	1976-01-21	Polymeres de type polyester a microstructure ordonnee, a poids moleculaire eleve et a faible viscosite

Publications (1)

Publication Number	Publication Date
CA1054745A true CA1054745A (fr)	1979-05-15

Family

ID=4105020

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA243977A Expired CA1054745A (fr)	1976-01-21	1976-01-21	Polymeres de type polyester a microstructure ordonnee, a poids moleculaire eleve et a faible viscosite

Country Status (1)

Country	Link
CA (1)	CA1054745A (fr)

1976
- 1976-01-21 CA CA243977A patent/CA1054745A/fr not_active Expired

Publication	Publication Date	Title
US3271368A (en)	1966-09-06	Sulfonate-thiocarbonate copolymers
US3701815A (en)	1972-10-31	Thermoplastic siloxane-polyester block copolymers
EP0237593B1 (fr)	1990-07-04	Copolymère de polysulfone-éther aromatique/polythioéther-sulfone et procédé pour sa préparation
CA1133185A (fr)	1982-10-05	Polyester-polycarbonate aromatique
US3772250A (en)	1973-11-13	Branched aromatic polyesters containing cyanuryl nucleus radicals
US4275186A (en)	1981-06-23	Oligomer extended polyarylethers
JPS6096619A (ja)	1985-05-30	リン‐改質ポリエステルカーボネート樹脂
US4330662A (en)	1982-05-18	Ordered copolyestercarbonate resins
US4829143A (en)	1989-05-09	Modified poly(aryl ether ketones) derived from biphenol
US4720537A (en)	1988-01-19	Branched copolyetherketones
US4278787A (en)	1981-07-14	Alternating copolyestercarbonate resins
US4552947A (en)	1985-11-12	Heat-resisting aromatic polyester and process for preparing the same
US4051107A (en)	1977-09-27	Microstructured high molecular weight-low viscosity polyester polymers
US2971944A (en)	1961-02-14	Maleimide polymers
EP0010840B1 (fr)	1985-12-04	Polyester-polycarbonate aromatique et procédé pour sa préparation
US4049629A (en)	1977-09-20	Solution polycondensation method
CA1054745A (fr)	1979-05-15	Polymeres de type polyester a microstructure ordonnee, a poids moleculaire eleve et a faible viscosite
US4782132A (en)	1988-11-01	Process for producing a copolyester
EP0015828B1 (fr)	1983-07-13	Polyarylates résistant à la fissuration sous contrainte et procédé de préparation
US4051106A (en)	1977-09-27	High molecular weight copolyester resins having a high degree of alternating structure
US4973650A (en)	1990-11-27	Polyarylsulfone derived from 1,4"-(bishalophenylsulfone)terphenyl
US3278640A (en)	1966-10-11	Segmented copolyester comprising aromatic and aliphatic polyester segments
US3274290A (en)	1966-09-20	Rigid, segmented copolyesters having recurring aromatic sulfonate ester units
JPH0536452B2 (fr)	1993-05-31
JPS61500555A (ja)	1986-03-27	コポリエ−テルイミドの製造方法