JPH0586423B2 - - Google Patents
Info
- Publication number
- JPH0586423B2 JPH0586423B2 JP59014991A JP1499184A JPH0586423B2 JP H0586423 B2 JPH0586423 B2 JP H0586423B2 JP 59014991 A JP59014991 A JP 59014991A JP 1499184 A JP1499184 A JP 1499184A JP H0586423 B2 JPH0586423 B2 JP H0586423B2
- Authority
- JP
- Japan
- Prior art keywords
- polymerization
- acid
- iron
- reaction
- temperature
- 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
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 126
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 111
- 238000006116 polymerization reaction Methods 0.000 claims description 95
- 229920000728 polyester Polymers 0.000 claims description 65
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 64
- 229910052742 iron Inorganic materials 0.000 claims description 58
- 238000006243 chemical reaction Methods 0.000 claims description 47
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 38
- 239000000178 monomer Substances 0.000 claims description 36
- 238000005886 esterification reaction Methods 0.000 claims description 35
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 claims description 29
- 239000000376 reactant Substances 0.000 claims description 28
- 238000006640 acetylation reaction Methods 0.000 claims description 24
- 230000032050 esterification Effects 0.000 claims description 21
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 claims description 18
- 230000021736 acetylation Effects 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 16
- KAUQJMHLAFIZDU-UHFFFAOYSA-N 6-Hydroxy-2-naphthoic acid Chemical compound C1=C(O)C=CC2=CC(C(=O)O)=CC=C21 KAUQJMHLAFIZDU-UHFFFAOYSA-N 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 9
- XBNGYFFABRKICK-UHFFFAOYSA-N 2,3,4,5,6-pentafluorophenol Chemical compound OC1=C(F)C(F)=C(F)C(F)=C1F XBNGYFFABRKICK-UHFFFAOYSA-N 0.000 claims description 7
- MCDLETWIOVSGJT-UHFFFAOYSA-N acetic acid;iron Chemical group [Fe].CC(O)=O.CC(O)=O MCDLETWIOVSGJT-UHFFFAOYSA-N 0.000 claims description 7
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 6
- 150000002506 iron compounds Chemical class 0.000 claims description 4
- 150000001261 hydroxy acids Chemical class 0.000 claims description 3
- 230000000977 initiatory effect Effects 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 description 80
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 63
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 41
- 239000000835 fiber Substances 0.000 description 31
- 230000000052 comparative effect Effects 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
- -1 aromatic diols Chemical class 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 238000010926 purge Methods 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- 238000002474 experimental method Methods 0.000 description 11
- 239000011521 glass Substances 0.000 description 10
- 239000000155 melt Substances 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- 238000000113 differential scanning calorimetry Methods 0.000 description 8
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 7
- 238000011065 in-situ storage Methods 0.000 description 7
- 238000004821 distillation Methods 0.000 description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000001632 sodium acetate Substances 0.000 description 5
- 235000017281 sodium acetate Nutrition 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000001479 atomic absorption spectroscopy Methods 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 230000001747 exhibiting effect Effects 0.000 description 4
- 238000001125 extrusion Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 235000011056 potassium acetate Nutrition 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000009987 spinning Methods 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000006114 decarboxylation reaction Methods 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000002685 polymerization catalyst Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- 238000004804 winding Methods 0.000 description 3
- SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 description 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 2
- AULKDLUOQCUNOK-UHFFFAOYSA-N 3,5-dichloro-4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC(Cl)=C(O)C(Cl)=C1 AULKDLUOQCUNOK-UHFFFAOYSA-N 0.000 description 2
- XMEQDAIDOBVHEK-UHFFFAOYSA-N 3-bromo-4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(Br)=C1 XMEQDAIDOBVHEK-UHFFFAOYSA-N 0.000 description 2
- QGNLHMKIGMZKJX-UHFFFAOYSA-N 3-chloro-4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(Cl)=C1 QGNLHMKIGMZKJX-UHFFFAOYSA-N 0.000 description 2
- OMNHTTWQSSUZHO-UHFFFAOYSA-N 4-hydroxy-3,5-dimethylbenzoic acid Chemical compound CC1=CC(C(O)=O)=CC(C)=C1O OMNHTTWQSSUZHO-UHFFFAOYSA-N 0.000 description 2
- LTFHNKUKQYVHDX-UHFFFAOYSA-N 4-hydroxy-3-methylbenzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1O LTFHNKUKQYVHDX-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 2
- 239000012345 acetylating agent Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 150000005165 hydroxybenzoic acids Chemical class 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MWQVQEFJAIFHFZ-UHFFFAOYSA-N 2,3-dichloro-4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(Cl)=C1Cl MWQVQEFJAIFHFZ-UHFFFAOYSA-N 0.000 description 1
- QTHMEINNGLIDSU-UHFFFAOYSA-N 2,5-dichloro-4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC(Cl)=C(O)C=C1Cl QTHMEINNGLIDSU-UHFFFAOYSA-N 0.000 description 1
- DNUYOWCKBJFOGS-UHFFFAOYSA-N 2-[[10-(2,2-dicarboxyethyl)anthracen-9-yl]methyl]propanedioic acid Chemical compound C1=CC=C2C(CC(C(=O)O)C(O)=O)=C(C=CC=C3)C3=C(CC(C(O)=O)C(O)=O)C2=C1 DNUYOWCKBJFOGS-UHFFFAOYSA-N 0.000 description 1
- WIPYZRZPNMUSER-UHFFFAOYSA-N 2-chloro-4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1Cl WIPYZRZPNMUSER-UHFFFAOYSA-N 0.000 description 1
- 229910000619 316 stainless steel Inorganic materials 0.000 description 1
- GDBUZIKSJGRBJP-UHFFFAOYSA-N 4-acetoxy benzoic acid Chemical compound CC(=O)OC1=CC=C(C(O)=O)C=C1 GDBUZIKSJGRBJP-UHFFFAOYSA-N 0.000 description 1
- CHHQEMBTCQDAHF-UHFFFAOYSA-N 4-hydroxy-2,3-dimethoxybenzoic acid Chemical compound COC1=C(O)C=CC(C(O)=O)=C1OC CHHQEMBTCQDAHF-UHFFFAOYSA-N 0.000 description 1
- FFUMDYCIOSWRLV-UHFFFAOYSA-N 4-hydroxy-2,6-dimethylbenzoic acid Chemical compound CC1=CC(O)=CC(C)=C1C(O)=O FFUMDYCIOSWRLV-UHFFFAOYSA-N 0.000 description 1
- 150000005168 4-hydroxybenzoic acids Chemical class 0.000 description 1
- MIBYFOLNIIUGNA-UHFFFAOYSA-N 5-chloro-6-hydroxynaphthalene-2-carboxylic acid Chemical compound ClC1=C(O)C=CC2=CC(C(=O)O)=CC=C21 MIBYFOLNIIUGNA-UHFFFAOYSA-N 0.000 description 1
- NFTLBCXRDNIJMI-UHFFFAOYSA-N 6-acetyloxynaphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(OC(=O)C)=CC=C21 NFTLBCXRDNIJMI-UHFFFAOYSA-N 0.000 description 1
- XKFNZRZICQABOD-UHFFFAOYSA-N 6-hydroxy-5-methylnaphthalene-2-carboxylic acid Chemical compound OC(=O)C1=CC=C2C(C)=C(O)C=CC2=C1 XKFNZRZICQABOD-UHFFFAOYSA-N 0.000 description 1
- JHXIMYHYJSQGGB-UHFFFAOYSA-N 7-chloro-6-hydroxynaphthalene-2-carboxylic acid Chemical compound C1=C(O)C(Cl)=CC2=CC(C(=O)O)=CC=C21 JHXIMYHYJSQGGB-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 229920001634 Copolyester Polymers 0.000 description 1
- 102100023849 Glycophorin-C Human genes 0.000 description 1
- 101100229307 Homo sapiens GYPC gene Proteins 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000003811 acetone extraction Methods 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 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 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- 239000004301 calcium benzoate Substances 0.000 description 1
- 235000010237 calcium benzoate Nutrition 0.000 description 1
- HZQXCUSDXIKLGS-UHFFFAOYSA-L calcium;dibenzoate;trihydrate Chemical compound O.O.O.[Ca+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 HZQXCUSDXIKLGS-UHFFFAOYSA-L 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- GHLITDDQOMIBFS-UHFFFAOYSA-H cerium(3+);tricarbonate Chemical compound [Ce+3].[Ce+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O GHLITDDQOMIBFS-UHFFFAOYSA-H 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- PNOXNTGLSKTMQO-UHFFFAOYSA-L diacetyloxytin Chemical compound CC(=O)O[Sn]OC(C)=O PNOXNTGLSKTMQO-UHFFFAOYSA-L 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium oxide Inorganic materials O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- YXEUGTSPQFTXTR-UHFFFAOYSA-K lanthanum(3+);trihydroxide Chemical compound [OH-].[OH-].[OH-].[La+3] YXEUGTSPQFTXTR-UHFFFAOYSA-K 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
- 239000011654 magnesium acetate Substances 0.000 description 1
- 235000011285 magnesium acetate Nutrition 0.000 description 1
- 229940069446 magnesium acetate Drugs 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002074 melt spinning Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IJFXRHURBJZNAO-UHFFFAOYSA-N meta--hydroxybenzoic acid Natural products OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- PVADDRMAFCOOPC-UHFFFAOYSA-N oxogermanium Chemical compound [Ge]=O PVADDRMAFCOOPC-UHFFFAOYSA-N 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002990 reinforced plastic Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- DPNUIZVZBWBCPB-UHFFFAOYSA-J titanium(4+);tetraphenoxide Chemical compound [Ti+4].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 DPNUIZVZBWBCPB-UHFFFAOYSA-J 0.000 description 1
- WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 description 1
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C08G63/065—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids the hydroxy and carboxylic ester groups being bound to aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/468,240 US4429105A (en) | 1983-02-22 | 1983-02-22 | Process for preparing a polyester of hydroxy naphthoic acid and hydroxy benzoic acid |
| US468,240 | 1983-02-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59157115A JPS59157115A (ja) | 1984-09-06 |
| JPH0586423B2 true JPH0586423B2 (US08063081-20111122-C00044.png) | 1993-12-13 |
Family
ID=23859000
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59014991A Granted JPS59157115A (ja) | 1983-02-22 | 1984-01-30 | ヒドロキシナフトエ酸とヒドロキシ安息香酸とのポリエステルの製法 |
Country Status (5)
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4574066A (en) * | 1984-02-27 | 1986-03-04 | Celanese Corporation | Process for the expeditious formation of a high strength shaped article of poly(6-oxy-2-naphthoate-4-oxybenzoate) |
| JPS6169866A (ja) * | 1984-09-12 | 1986-04-10 | Polyplastics Co | 複合材料組成物 |
| JP2664400B2 (ja) * | 1988-03-24 | 1997-10-15 | ポリプラスチックス 株式会社 | 溶融時に異方性を示すポリエステル樹脂及び樹脂組成物 |
| US5015723A (en) * | 1988-09-02 | 1991-05-14 | Sumitomo Chemical Company, Limited | Process for producing aromatic polyesters |
| JP2847188B2 (ja) * | 1988-11-04 | 1999-01-13 | 住友化学工業株式会社 | 芳香族ポリエステルの製造方法 |
| US5064930A (en) * | 1990-09-27 | 1991-11-12 | Eastman Kodak Company | Solid phase polyarylate process |
| IT1256918B (it) * | 1992-08-04 | 1995-12-27 | Mini Ricerca Scient Tecnolog | Procedimento per la produzione di poli acido lattico. |
| US5472658A (en) * | 1993-12-22 | 1995-12-05 | Holechst Celanese Corporation | Pre-stressing of heat treated liquid crystalline polymer fiber to improve modulus |
| US6114492A (en) * | 2000-01-14 | 2000-09-05 | Ticona Llc | Process for producing liquid crystal polymer |
| JP4972832B2 (ja) * | 2001-07-25 | 2012-07-11 | 東レ株式会社 | 液晶ポリエステル樹脂組成物の製造方法 |
| JP4681268B2 (ja) * | 2004-10-07 | 2011-05-11 | 上野製薬株式会社 | 全芳香族液晶ポリエステル樹脂の製造方法 |
| US20100184348A1 (en) * | 2006-12-20 | 2010-07-22 | Imerys Pigments, Inc. | Spunlaid Fibers Comprising Coated Calcium Carbonate, Processes For Their Production, and Nonwoven Products |
| ATE525182T1 (de) | 2007-06-03 | 2011-10-15 | Imerys Pigments Inc | Gesponnene fasern mit beschichtetem kalziumkarbonat, verfahren zu ihrer herstellung und vliesprodukte |
| US20110059287A1 (en) * | 2008-01-21 | 2011-03-10 | Imerys Pigments, Inc. | Fibers comprising at least one filler, processes for their production, and uses thereof |
| EP2245077B1 (en) * | 2008-01-21 | 2018-06-06 | Imerys Pigments, Inc. | Monofilament fibers comprising ground calcium carbonate |
| US20100035045A1 (en) * | 2008-01-21 | 2010-02-11 | Imerys Pigments, Inc. | Fibers comprising at least one filler and processes for their production |
| US10156303B2 (en) | 2010-12-22 | 2018-12-18 | Ticona Llc | High temperature conduit having a complex, three-dimensional configuration |
| US20130052447A1 (en) | 2011-08-29 | 2013-02-28 | Ticona Llc | Liquid Crystalline Polymer Composition Containing a Fibrous Filler |
| TW201313884A (zh) | 2011-08-29 | 2013-04-01 | Ticona Llc | 液晶聚合物之固態聚合 |
| US20130053531A1 (en) | 2011-08-29 | 2013-02-28 | Ticona Llc | Method for Minimizing Process Disruptions During Formation of a Liquid Crystalline Polymer |
| US9096794B2 (en) | 2011-08-29 | 2015-08-04 | Ticona Llc | High flow liquid crystalline polymer composition |
| CN103764793B (zh) | 2011-08-29 | 2016-09-14 | 提克纳有限责任公司 | 高流动液晶聚合物组合物 |
| WO2013032977A1 (en) | 2011-08-29 | 2013-03-07 | Ticona Llc | Heat-resistant liquid crystalline polymer composition having a low melting temperature |
| JP2014525500A (ja) | 2011-08-29 | 2014-09-29 | ティコナ・エルエルシー | 低溶融粘度液晶ポリマーの溶融重合 |
| US8778221B2 (en) | 2011-08-29 | 2014-07-15 | Ticona Llc | Aromatic amide compound |
| WO2013032967A1 (en) | 2011-08-29 | 2013-03-07 | Ticona Llc | Cast molded parts formed form a liquid crystalline polymer |
| TW201319023A (zh) | 2011-08-29 | 2013-05-16 | Ticona Llc | 具改良低剪切黏度之熱向性液晶聚合物 |
| US8852730B2 (en) | 2011-08-29 | 2014-10-07 | Ticona Llc | Melt-extruded substrate for use in thermoformed articles |
| US8618239B2 (en) | 2011-09-30 | 2013-12-31 | Ticona Llc | Solid-stage polymerization system for a liquid crystalline polymer |
| JP6152114B2 (ja) | 2011-10-31 | 2017-06-21 | ティコナ・エルエルシー | レーザーダイレクトストラクチャード基板を形成する際に使用するための熱可塑性組成物 |
| WO2013074476A1 (en) | 2011-11-15 | 2013-05-23 | Ticona Llc | Low naphthenic liquid crystalline polymer composition |
| WO2013074470A2 (en) | 2011-11-15 | 2013-05-23 | Ticona Llc | Fine pitch electrical connector and a thermoplastic composition for use therein |
| US8906259B2 (en) | 2011-11-15 | 2014-12-09 | Ticona Llc | Naphthenic-rich liquid crystalline polymer composition with improved flammability performance |
| KR101996106B1 (ko) | 2011-11-15 | 2019-07-03 | 티코나 엘엘씨 | 치수 공차가 작은 성형 부품에 사용하기 위한 저-나프텐 액정 중합체 조성물 |
| TWI464244B (zh) | 2011-11-15 | 2014-12-11 | Ticona Llc | 用於高壓電子組件之液晶聚合物組合物 |
| KR102098411B1 (ko) | 2011-11-15 | 2020-04-07 | 티코나 엘엘씨 | 콤팩트 카메라 모듈 |
| US20130119317A1 (en) | 2011-11-15 | 2013-05-16 | Ticona Llc | Method for Forming a Liquid Crystalline Thermoplastic Composition |
| TWI464245B (zh) | 2012-06-27 | 2014-12-11 | Ticona Llc | 超低黏度之液晶聚合物組合物 |
| US9206300B2 (en) | 2013-06-07 | 2015-12-08 | Ticona Llc | High strength thermotropic liquid crystalline polymer |
| WO2019099090A1 (en) | 2017-11-15 | 2019-05-23 | Exxonmobil Chemical Patents Inc. | Liquid crystalline polyester compositions and methods |
| CA3095475A1 (en) | 2018-03-29 | 2019-10-03 | Atex Technologies, Inc. | Small diameter, high strength, low elongation, creep resistant, abrasion resistant braided structure |
| TWI740515B (zh) | 2019-12-23 | 2021-09-21 | 長春人造樹脂廠股份有限公司 | 液晶高分子膜及包含其之積層板 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5477691A (en) * | 1977-10-20 | 1979-06-21 | Celanese Corp | Polyester composed of 66hydroxyy 22naphtoic acid and pphydroxy benzoic acid* which enable melt processing to be easy |
| JPS5594930A (en) * | 1979-01-10 | 1980-07-18 | Sumitomo Chem Co Ltd | Preparation of aromatic polyester by improved bulk polymerization process |
| JPS56136818A (en) * | 1980-03-10 | 1981-10-26 | Celanese Corp | Anisotropic melt formable polyester of phenyl-4-hydroxybenzoic acid and 4-hydroxybenzoic acid and/or 6-hydroxy-2-naphthoic acid |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2740768A (en) * | 1954-06-17 | 1956-04-03 | Goodyear Tire & Rubber | Production of polyesters using basic ferric acetate as catalyst |
| FR1324085A (fr) * | 1961-05-01 | 1963-04-12 | Ici Ltd | Polyesters dont la tendance à la formation de couleur est supprimée |
| US3975487A (en) * | 1973-08-20 | 1976-08-17 | The Carborundum Company | Process for spinning high modulus oxybenzoyl copolyester fibers |
| US4219461A (en) | 1979-04-23 | 1980-08-26 | Celanese Corporation | Polyester of 6-hydroxy-2-naphthoic acid, para-hydroxy benzoic acid, aromatic diol, and aromatic diacid capable of readily undergoing melt processing |
| US4256624A (en) | 1979-07-02 | 1981-03-17 | Celanese Corporation | Polyester of 6-hydroxy-2-naphthoic acid, aromatic diol, and aromatic diacid capable of undergoing melt processing |
| JPS5657821A (en) * | 1979-10-18 | 1981-05-20 | Sumitomo Chem Co Ltd | Preparation of aromatic polyester |
| US4337190A (en) | 1980-07-15 | 1982-06-29 | Celanese Corporation | Polyester of 6-hydroxy-2-naphthoic acid and meta-hydroxy benzoic acid capable of readily undergoing melt processing |
| US4359569A (en) | 1980-10-17 | 1982-11-16 | E. I. Du Pont De Nemours And Company | Aromatic polyester and filaments |
| US4355134A (en) | 1981-06-04 | 1982-10-19 | Celanese Corporation | Wholly aromatic polyester capable of forming an anisotropic melt phase at an advantageously reduced temperature |
| US4355133A (en) | 1981-07-27 | 1982-10-19 | Celanese Corporation | Polyester of 6-hydroxy-2-naphthoic acid, 4-hydroxy benzoic acid, 1,4-cyclohexanedicarboxylic acid, and aromatic diol capable of readily undergoing melt processing to form articles possessing high impact properties |
| US4370466A (en) | 1981-09-28 | 1983-01-25 | E. I. Du Pont De Nemours And Company | Optically anisotropic melt forming polyesters |
| US4395536A (en) * | 1981-11-17 | 1983-07-26 | Celanese Corporation | Preparation of aromatic copolyesters via in situ esterification with isopropenyl esters of an alkyl acid |
-
1983
- 1983-02-22 US US06/468,240 patent/US4429105A/en not_active Expired - Lifetime
-
1984
- 1984-01-24 CA CA000445955A patent/CA1219992A/en not_active Expired
- 1984-01-30 JP JP59014991A patent/JPS59157115A/ja active Granted
- 1984-01-31 DE DE8484300598T patent/DE3470165D1/de not_active Expired
- 1984-01-31 EP EP84300598A patent/EP0117086B1/en not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5477691A (en) * | 1977-10-20 | 1979-06-21 | Celanese Corp | Polyester composed of 66hydroxyy 22naphtoic acid and pphydroxy benzoic acid* which enable melt processing to be easy |
| JPS5594930A (en) * | 1979-01-10 | 1980-07-18 | Sumitomo Chem Co Ltd | Preparation of aromatic polyester by improved bulk polymerization process |
| JPS56136818A (en) * | 1980-03-10 | 1981-10-26 | Celanese Corp | Anisotropic melt formable polyester of phenyl-4-hydroxybenzoic acid and 4-hydroxybenzoic acid and/or 6-hydroxy-2-naphthoic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1219992A (en) | 1987-03-31 |
| EP0117086A3 (en) | 1985-08-21 |
| US4429105A (en) | 1984-01-31 |
| EP0117086B1 (en) | 1988-03-30 |
| EP0117086A2 (en) | 1984-08-29 |
| JPS59157115A (ja) | 1984-09-06 |
| DE3470165D1 (en) | 1988-05-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |