JPH06502668A - テレフタル酸、2,6−ナフタレンジカルボン酸及びハイドロキノンからのポリエステル - Google Patents
テレフタル酸、2,6−ナフタレンジカルボン酸及びハイドロキノンからのポリエステルInfo
- Publication number
- JPH06502668A JPH06502668A JP4500968A JP50096892A JPH06502668A JP H06502668 A JPH06502668 A JP H06502668A JP 4500968 A JP4500968 A JP 4500968A JP 50096892 A JP50096892 A JP 50096892A JP H06502668 A JPH06502668 A JP H06502668A
- Authority
- JP
- Japan
- Prior art keywords
- polyester
- mol
- acid
- component
- aromatic
- 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.)
- Granted
Links
- 229920000728 polyester Polymers 0.000 title claims description 59
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 title claims description 28
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 title claims description 26
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 title claims description 12
- -1 aromatic diol Chemical class 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 22
- 238000002844 melting Methods 0.000 claims description 14
- 230000008018 melting Effects 0.000 claims description 14
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 4
- 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 4
- 150000002366 halogen compounds Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- 229920006380 polyphenylene oxide Polymers 0.000 claims description 4
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 claims description 4
- 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 3
- XCZKKZXWDBOGPA-UHFFFAOYSA-N 2-phenylbenzene-1,4-diol Chemical compound OC1=CC=C(O)C(C=2C=CC=CC=2)=C1 XCZKKZXWDBOGPA-UHFFFAOYSA-N 0.000 claims description 3
- 229920000049 Carbon (fiber) Polymers 0.000 claims description 3
- 239000004677 Nylon Substances 0.000 claims description 3
- 239000004734 Polyphenylene sulfide Substances 0.000 claims description 3
- 239000004793 Polystyrene Substances 0.000 claims description 3
- 239000004917 carbon fiber Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- AJPXTSMULZANCB-UHFFFAOYSA-N chlorohydroquinone Chemical compound OC1=CC=C(O)C(Cl)=C1 AJPXTSMULZANCB-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 150000002009 diols Chemical class 0.000 claims description 3
- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 claims description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229920001778 nylon Polymers 0.000 claims description 3
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 claims description 3
- 239000004417 polycarbonate Substances 0.000 claims description 3
- 229920000515 polycarbonate Polymers 0.000 claims description 3
- 229920000069 polyphenylene sulfide Polymers 0.000 claims description 3
- 229920002223 polystyrene Polymers 0.000 claims description 3
- 150000003457 sulfones Chemical class 0.000 claims description 3
- OFRAHNPFMRGJFL-UHFFFAOYSA-N 2-(2-phenylethyl)benzene-1,4-diol Chemical compound OC1=CC=C(O)C(CCC=2C=CC=CC=2)=C1 OFRAHNPFMRGJFL-UHFFFAOYSA-N 0.000 claims description 2
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 claims description 2
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 claims description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 238000000227 grinding Methods 0.000 claims description 2
- 239000010445 mica Substances 0.000 claims description 2
- 229910052618 mica group Inorganic materials 0.000 claims description 2
- 238000005453 pelletization Methods 0.000 claims description 2
- 229920012287 polyphenylene sulfone Polymers 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 239000003607 modifier Substances 0.000 claims 2
- 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 claims 1
- 229920002292 Nylon 6 Polymers 0.000 claims 1
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 claims 1
- 150000001463 antimony compounds Chemical class 0.000 claims 1
- ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical compound OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 claims 1
- 239000003000 extruded plastic Substances 0.000 claims 1
- 239000002991 molded plastic Substances 0.000 claims 1
- DFFZOPXDTCDZDP-UHFFFAOYSA-N naphthalene-1,5-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1C(O)=O DFFZOPXDTCDZDP-UHFFFAOYSA-N 0.000 claims 1
- WPUMVKJOWWJPRK-UHFFFAOYSA-N naphthalene-2,7-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 WPUMVKJOWWJPRK-UHFFFAOYSA-N 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 229920001643 poly(ether ketone) Polymers 0.000 claims 1
- 229920001601 polyetherimide Polymers 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001261 hydroxy acids Chemical class 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920002492 poly(sulfone) Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UOFDVLCOMURSTA-UHFFFAOYSA-N 2-(2-carboxyphenoxy)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1C(O)=O UOFDVLCOMURSTA-UHFFFAOYSA-N 0.000 description 1
- REFDOIWRJDGBHY-UHFFFAOYSA-N 2-bromobenzene-1,4-diol Chemical compound OC1=CC=C(O)C(Br)=C1 REFDOIWRJDGBHY-UHFFFAOYSA-N 0.000 description 1
- ZPXGNBIFHQKREO-UHFFFAOYSA-N 2-chloroterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(Cl)=C1 ZPXGNBIFHQKREO-UHFFFAOYSA-N 0.000 description 1
- SBBQDUFLZGOASY-OWOJBTEDSA-N 4-[(e)-2-(4-carboxyphenyl)ethenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1\C=C\C1=CC=C(C(O)=O)C=C1 SBBQDUFLZGOASY-OWOJBTEDSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- ODPYDILFQYARBK-UHFFFAOYSA-N 7-thiabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2SC2=C1 ODPYDILFQYARBK-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920001634 Copolyester Polymers 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 229920004142 LEXAN™ Polymers 0.000 description 1
- 239000004418 Lexan Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 239000004974 Thermotropic liquid crystal Substances 0.000 description 1
- 229920004738 ULTEM® Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 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
- 238000013459 approach Methods 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000001142 dicarboxylic acid group Chemical group 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000010309 melting process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000005209 naphthoic acids Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229920003208 poly(ethylene sulfide) Polymers 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 125000004151 quinonyl group Chemical group 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 150000003504 terephthalic acids Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229910000634 wood's metal Inorganic materials 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
- C08G63/78—Preparation processes
-
- 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
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
- C08G63/185—Acids containing aromatic rings containing two or more aromatic rings
- C08G63/187—Acids containing aromatic rings containing two or more aromatic rings containing condensed aromatic rings
- C08G63/189—Acids containing aromatic rings containing two or more aromatic rings containing condensed aromatic rings containing a naphthalene ring
-
- 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
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/19—Hydroxy compounds containing aromatic rings
- C08G63/191—Hydroquinones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
- C08L67/03—Polyesters derived from dicarboxylic acids and dihydroxy compounds the dicarboxylic acids and dihydroxy compounds having the carboxyl- and the hydroxy groups directly linked 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)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Artificial Filaments (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.(A)35〜60モル%のテレフタル酸繰返し単位及び65〜40モル%の 2,6−ナフタレンジカルボン酸繰返し単位を含んで成る酸成分並びに (B)少なくとも90モル%のハイドロキノン繰返し単位を含んで成る芳香族ジ オール成分を含んで成り、酸成分及び芳香族ジオール成分の全モル%が各100 モル%であり、かつペンタフルオロフェノール中に不溶性で450℃より低い融 点を有する全芳香族非置換ポリエステル。 2.酸成分がテレフタル酸40〜50モル%及び2,6−ナフタレンジカルボン 酸60〜50モル%の繰返し単位から成る請求の範囲第1項に記載のポリエステ ル。 3,芳香族ジオール成分がハイドロキノン100モル%の繰返し単位から成る請 求の範囲第1項に記載のポリエステル。 4.酸成分及び芳香族ジオール成分が対称的である請求の範囲第1項に記載のポ リエステル。 5.酸成分が20モル%以下の少なくとも一種の他の芳香族ジカルボン酸を含む 請求の範囲第1項に記載のポリエステル。 6.酸成分が10モル%以下の少なくとも一種の他の芳香族ジカルボン酸を含む 請求の範囲第5項に記載のポリエステル。 7.ジカルボン酸がイソフタル酸、4,4′−ジフェニルジカルボン酸、1,5 −ナフタレンジカルボン酸、2,6−ナフタレンジカルボン酸、2,7−ナフタ レンジカルボン酸、4,4′−オキシジ安息香酸及びトランス−4,4′−スチ ルベン−ジカルボン酸から成る群から選ばれたものである請求の範囲第6項に記 載のポリエステル。 8.芳香族ジオール成分が10モル%以下の少なくとも一種の他の芳香族ジオー ルを含む請求の範囲第1項に記載のポリエステル。 9.芳香族ジオール成分が5モル%以下の少なくとも一種の他の芳香族ジオール を含む請求の範囲第8項に記載のポリエステル。 10.他の芳香族ジオール成分がビスフェノールA、4,4′−ジヒドロキシジ フェニルスルホン、2−メチルヒドロキノン、2−クロロヒドロキノン、2−( フェニルエチル)ヒドロキノン、2−フェニルヒドロキノン、2−シクロヘキシ ルヒドロキノン及び4,4′−ビフェノールから成る選ばれたものである請求の 範囲第9項に記載のポリエステル。 11.(i)請求の範囲第1項のポリエステル5〜95重量%及び(ii)少な くとも一種の性質改良剤95〜5重量%から成る組成物。 12.成分(i)が10〜90重量%の量で存在し、そして成分(ii)が90 〜10重量%の量で存在する請求の範囲第11項に記載の組成物。 13.性質改良剤が6,6−ナイロン、ナイロン−6、ポリ(エ−テルイミド) 、ポリフェニレンオキサイド、ポリフェニレンオキサイド/ポリスチレンブレン ド、別のポリエステル、ポリフェニレンスルフィド、ポリフェニレンスルフィド /スルホンブレンド、ポリ(エステル−カーボネイト)、ポリカーボネート、ポ リスルホンエーテル、ポリ(エーテル−ケトン)、リン化合物、ハロゲン化合物 、ハロゲン化合物とアンチモン化合物との組み合わせ、タルク、マイカ。、ガラ ス繊維又は炭素繊維である請求の範囲第11項に記載の組成物。 14.請求の範囲第1項のポリエステルを含んで成る成型プラスチック。 15.請求の範囲第1項のポリエステルを含んで成る押出プラスチック。 16.請求の範囲第1項のポリエステルを含んで成る繊維。 17.請求の範囲第1項のポリエステルを含んで成るフィルム。 18.(a)重合条件下に、(A)35〜60モル%のテレフタル酸及び65〜 40モル%の2,6−ナフタレンジカルボン酸を含んで成る酸成分並びに(B) 少なくとも90モル%のハイドロキノンを含んで成る芳香族ジオール成分(但し 、酸成分及び芳香族ジオール成分の全モル%はそれぞれ100モル%である)を 混合することによって、ペンタフルオロフエノールに不溶性で450℃より低い 融点のポリエステルを製造し、 (b)前記ポリエステルを粉砕又はペレット化し、(c)部分真空又は窒素バー ジ下に200〜400℃の温度で(b)の粒状ポリエステルを加熱し、反応副生 物を除去し、ポリエステルの分子量を増大させることを含んで成る全芳香族ポリ エステルの製造方法。 19.工程(c)を300〜400℃の温度で行う請求の範囲第18項に記載の 方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/614,320 US5221730A (en) | 1990-11-16 | 1990-11-16 | Polyesters from terephthalic acid, 2,6-naphthalenedicarboxylic acid and hydroquinone |
US614,320 | 1990-11-16 | ||
PCT/US1991/008395 WO1992008750A1 (en) | 1990-11-16 | 1991-11-15 | Polyesters from terephthalic acid, 2,6-naphthalenedicarboxylic acid and hydroquinone |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH06502668A true JPH06502668A (ja) | 1994-03-24 |
JP3121012B2 JP3121012B2 (ja) | 2000-12-25 |
Family
ID=24460743
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP04500968A Expired - Lifetime JP3121012B2 (ja) | 1990-11-16 | 1991-11-15 | テレフタル酸、2,6−ナフタレンジカルボン酸及びハイドロキノンからのポリエステル |
Country Status (8)
Country | Link |
---|---|
US (1) | US5221730A (ja) |
EP (1) | EP0557384B1 (ja) |
JP (1) | JP3121012B2 (ja) |
AT (1) | ATE151087T1 (ja) |
CA (1) | CA2094375C (ja) |
DE (1) | DE69125501T2 (ja) |
DK (1) | DK0557384T3 (ja) |
WO (1) | WO1992008750A1 (ja) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0637642B1 (en) * | 1993-01-07 | 2002-02-13 | Unitika Ltd. | Binder fiber and nonwoven fabric produced therefrom |
US5646077A (en) * | 1993-01-07 | 1997-07-08 | Unitika Ltd | Binder fiber and nonwoven fabrics using the fiber |
US5710237A (en) * | 1994-09-06 | 1998-01-20 | E. I. Du Pont De Nemours And Company | Liquid crystalline polyester resin |
US5614599A (en) * | 1994-10-31 | 1997-03-25 | The Dow Chemical Company | Stilbene-based polyester and polycarbonate compositions |
US6150473A (en) * | 1998-12-14 | 2000-11-21 | General Electric Company | Polyetherimide resin/polyester resin blends having improved properties |
US6403684B1 (en) | 1998-12-16 | 2002-06-11 | General Electric Company | Polyetherimide resin/polyester resin blends having improved visual clarity |
US6503964B2 (en) * | 2000-01-11 | 2003-01-07 | Cool Options, Inc. | Polymer composition with metal coated carbon flakes |
JP2014525501A (ja) | 2011-08-29 | 2014-09-29 | ティコナ・エルエルシー | 高流動性液晶ポリマー組成物 |
KR20140059825A (ko) | 2011-08-29 | 2014-05-16 | 티코나 엘엘씨 | 고유동성 액정 중합체 조성물 |
WO2013032974A1 (en) | 2011-08-29 | 2013-03-07 | Ticona Llc | Solid-state polymerization of a liquid crystalline polymer |
JP2014525499A (ja) | 2011-08-29 | 2014-09-29 | ティコナ・エルエルシー | 低い融解温度をもつ耐熱性液晶ポリマー組成物 |
WO2013032971A1 (en) | 2011-08-29 | 2013-03-07 | Ticona Llc | Melt-extruded substrate for use in thermoformed articles |
US9057016B2 (en) | 2011-08-29 | 2015-06-16 | Ticona Llc | Melt polymerization of low melt viscosity liquid crystalline polymers |
WO2013032975A1 (en) | 2011-08-29 | 2013-03-07 | Ticona Llc | Thermotropic liquid crystalline polymer with improved low shear viscosity |
KR20140057629A (ko) | 2011-08-29 | 2014-05-13 | 티코나 엘엘씨 | 방향족 아마이드 화합물 |
WO2013032967A1 (en) | 2011-08-29 | 2013-03-07 | Ticona Llc | Cast molded parts formed form a liquid crystalline polymer |
CN113912988A (zh) | 2013-06-07 | 2022-01-11 | 提克纳有限责任公司 | 高强度热致液晶聚合物 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3030335A (en) * | 1959-01-02 | 1962-04-17 | Gen Electric | Aromatic polycarbonate reaction products |
US3036990A (en) * | 1960-06-01 | 1962-05-29 | Gen Electric | Wholly aromatic polyesters from hydroquinone, isophthalic and terephthalic acid reactants |
US3160604A (en) * | 1961-06-01 | 1964-12-08 | Mbltino fo | |
DE1769930A1 (de) * | 1967-09-05 | 1971-09-16 | Sun Oil Co | Lineare Polyester,die Naphthalin-2,6-dicarboxylat und Terephthalat enthalten |
US3637595A (en) * | 1969-05-28 | 1972-01-25 | Steve G Cottis | P-oxybenzoyl copolyesters |
US4156070A (en) * | 1977-08-08 | 1979-05-22 | Eastman Kodak Company | Liquid crystal copolyesters prepared from an aromatic dicarboxylic acid, a substituted hydroquinone and resorcinol |
US4146702A (en) * | 1977-08-08 | 1979-03-27 | Eastman Kodak Company | Liquid crystal copolyesters prepared from an aromatic dicarboxylic acid, a substituted hydroquinone and a m-acyloxybenzoic acid |
US4169933A (en) * | 1977-08-08 | 1979-10-02 | Eastman Kodak Company | Liquid crystal copolyesters containing terephthalic acid and 2,6-naphthalenedicarboxylic acid |
US4184996A (en) * | 1977-09-12 | 1980-01-22 | Celanese Corporation | Melt processable thermotropic wholly aromatic polyester |
US4181792A (en) * | 1978-03-20 | 1980-01-01 | Eastman Kodak Company | Liquid crystal copolyesters containing terephthalic acid, isophthalic acid, 2,6-naphthalenedicarboxylic acid and hydroquinone |
US4201856A (en) * | 1978-05-08 | 1980-05-06 | Eastman Kodak Company | Liquid crystal copolyesters containing terephthalic acid, 2,6-naphthalenedicarboxylic acid, hydroquinone and resorcinol |
US4380598A (en) * | 1981-02-12 | 1983-04-19 | Union Carbide Corporation | Flame retardant polyarylate compositions |
US5025082A (en) * | 1988-08-24 | 1991-06-18 | Mitsubishi Kasei Corporation | Aromatic polyester, aromatic polyester-amide and processes for producing the same |
-
1990
- 1990-11-16 US US07/614,320 patent/US5221730A/en not_active Expired - Lifetime
-
1991
- 1991-11-15 DK DK91920391.9T patent/DK0557384T3/da active
- 1991-11-15 WO PCT/US1991/008395 patent/WO1992008750A1/en active IP Right Grant
- 1991-11-15 CA CA002094375A patent/CA2094375C/en not_active Expired - Fee Related
- 1991-11-15 AT AT91920391T patent/ATE151087T1/de active
- 1991-11-15 DE DE69125501T patent/DE69125501T2/de not_active Expired - Lifetime
- 1991-11-15 JP JP04500968A patent/JP3121012B2/ja not_active Expired - Lifetime
- 1991-11-15 EP EP91920391A patent/EP0557384B1/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
CA2094375A1 (en) | 1992-05-17 |
EP0557384B1 (en) | 1997-04-02 |
EP0557384A1 (en) | 1993-09-01 |
DK0557384T3 (da) | 1997-10-13 |
DE69125501D1 (de) | 1997-05-07 |
JP3121012B2 (ja) | 2000-12-25 |
WO1992008750A1 (en) | 1992-05-29 |
ATE151087T1 (de) | 1997-04-15 |
CA2094375C (en) | 1997-10-14 |
DE69125501T2 (de) | 1997-08-14 |
US5221730A (en) | 1993-06-22 |
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