CA1123993A - Melt processable thermotropic wholly aromatic polyester - Google Patents
Melt processable thermotropic wholly aromatic polyesterInfo
- Publication number
- CA1123993A CA1123993A CA309,912A CA309912A CA1123993A CA 1123993 A CA1123993 A CA 1123993A CA 309912 A CA309912 A CA 309912A CA 1123993 A CA1123993 A CA 1123993A
- Authority
- CA
- Canada
- Prior art keywords
- aromatic polyester
- wholly aromatic
- melt
- moiety
- approximately
- 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
Links
- 229920000728 polyester Polymers 0.000 title claims abstract description 85
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 79
- 239000000155 melt Substances 0.000 claims abstract description 21
- 238000006467 substitution reaction Methods 0.000 claims abstract description 5
- 239000007787 solid Substances 0.000 claims description 8
- 238000000465 moulding Methods 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000000945 filler Substances 0.000 claims description 3
- 239000012744 reinforcing agent Substances 0.000 claims description 3
- 229920001169 thermoplastic Polymers 0.000 claims 1
- 239000004416 thermosoftening plastic Substances 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 21
- 238000006116 polymerization reaction Methods 0.000 abstract description 17
- 238000002844 melting Methods 0.000 abstract description 15
- 230000008018 melting Effects 0.000 abstract description 15
- 238000010128 melt processing Methods 0.000 abstract description 7
- 239000002002 slurry Substances 0.000 abstract description 7
- 229920000642 polymer Polymers 0.000 description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- 239000000835 fiber Substances 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 14
- -1 isophthaloyl moiety Chemical group 0.000 description 14
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- 239000000376 reactant Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241000790917 Dioxys <bee> Species 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 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 4
- 239000002253 acid Substances 0.000 description 4
- 239000003570 air Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000006835 compression Effects 0.000 description 4
- 238000007906 compression Methods 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000001125 extrusion Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000007669 thermal treatment Methods 0.000 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 description 3
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 3
- 238000001746 injection moulding Methods 0.000 description 3
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000007790 solid phase Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002074 melt spinning Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical group C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000001911 terphenyls Chemical class 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- GRYSXUXXBDSYRT-WOUKDFQISA-N (2r,3r,4r,5r)-2-(hydroxymethyl)-4-methoxy-5-[6-(methylamino)purin-9-yl]oxolan-3-ol Chemical compound C1=NC=2C(NC)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1OC GRYSXUXXBDSYRT-WOUKDFQISA-N 0.000 description 1
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 1
- KZCDMIJHGSSDFO-UHFFFAOYSA-N 1-methyl-2-(2-methylphenyl)sulfonylbenzene Chemical compound CC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1C KZCDMIJHGSSDFO-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 125000005362 aryl sulfone group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000002844 continuous effect Effects 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- OYFJQPXVCSSHAI-QFPUQLAESA-N enalapril maleate Chemical compound OC(=O)\C=C/C(O)=O.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 OYFJQPXVCSSHAI-QFPUQLAESA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000007750 plasma spraying Methods 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
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000012066 reaction slurry Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000000646 scanning calorimetry Methods 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000012899 standard injection Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/78—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolycondensation products
- D01F6/84—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolycondensation products from copolyesters
-
- 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
- C08G63/60—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds
- C08G63/605—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds the hydroxy and carboxylic groups being bound to aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Artificial Filaments (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83214777A | 1977-09-12 | 1977-09-12 | |
| US877,917 | 1978-02-15 | ||
| US05/877,917 US4184996A (en) | 1977-09-12 | 1978-02-15 | Melt processable thermotropic wholly aromatic polyester |
| US832,147 | 1997-04-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1123993A true CA1123993A (en) | 1982-05-18 |
Family
ID=27125491
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA309,912A Expired CA1123993A (en) | 1977-09-12 | 1978-08-23 | Melt processable thermotropic wholly aromatic polyester |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4184996A (OSRAM) |
| EP (1) | EP0001340B1 (OSRAM) |
| JP (1) | JPS5450594A (OSRAM) |
| CA (1) | CA1123993A (OSRAM) |
| DE (1) | DE2861360D1 (OSRAM) |
Families Citing this family (111)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4161470A (en) * | 1977-10-20 | 1979-07-17 | Celanese Corporation | Polyester of 6-hydroxy-2-naphthoic acid and para-hydroxy benzoic acid capable of readily undergoing melt processing |
| US4188476A (en) * | 1979-04-06 | 1980-02-12 | E. I. Du Pont De Nemours And Company | Aromatic polyester consisting essentially of p-oxybenzoyl units, terephthaloyl units, 2,6-dioxynaphthalene or 2,6-dioxyanthraquinone units and m-oxybenzoyl or 1,3-dioxyphenylene units |
| US4337191A (en) * | 1979-11-05 | 1982-06-29 | Fiber Industries, Inc. | Polyester of para-hydroxy benzoic acid, 2,6-naphthalene dicarboxylic acid, terephthalic acid and methylhydroquinone exhibiting improved hydrolytic stability and which is capable of forming an anisotropic melt |
| US4299756A (en) * | 1980-03-10 | 1981-11-10 | Celanese Corporation | Polyester of phenyl-4-hydroxybenzoic acid, aromatic diol, and aromatic diacid capable of forming an anisotropic melt |
| US4279803A (en) * | 1980-03-10 | 1981-07-21 | Celanese Corporation | Polyester of phenyl-4-hydroxybenzoic acid and 4-hydroxybenzoic acid and/or 6-hydroxy-2-naphthoic acid capable of forming an anisotropic melt |
| US4489190A (en) * | 1980-06-11 | 1984-12-18 | Celanese Corporation | Blend of polyalkylene terephthalate and wholly aromatic polyester |
| US4460735A (en) * | 1980-07-03 | 1984-07-17 | Celanese Corporation | Blend of polycarbonate and wholly aromatic polyester |
| US4267289A (en) * | 1980-07-03 | 1981-05-12 | Celanese Corporation | Blend of wholly aromatic polyesters |
| US4460736A (en) * | 1980-07-03 | 1984-07-17 | Celanese Corporation | Blend of sulfone polymer and wholly aromatic polyester |
| US4332759A (en) * | 1980-07-15 | 1982-06-01 | Celanese Corporation | Process for extruding liquid crystal polymer |
| US4325903A (en) * | 1980-07-15 | 1982-04-20 | Celanese Corporation | Processing of melt processible liquid crystal polymer by control of thermal history |
| US4318842A (en) * | 1980-10-06 | 1982-03-09 | Celanese Corporation | Polyester of 6-hydroxy-2-naphthoic acid, aromatic diol, and 1,4-cyclohexanedicarboxylic acid capable of undergoing melt processing |
| US4355152A (en) * | 1980-11-19 | 1982-10-19 | Celanese Corporation | Solvent resistant halogenated aromatic polyester fibers and process therefor |
| US4346209A (en) * | 1980-11-19 | 1982-08-24 | Celanese Corporation | Solvent resistant halogenated aromatic polyester fibers and process therefor |
| 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 |
| US4384016A (en) * | 1981-08-06 | 1983-05-17 | Celanese Corporation | Mutiaxially oriented high performance laminates comprised of uniaxially oriented sheets of thermotropic liquid crystal polymers |
| US4394498A (en) * | 1981-08-24 | 1983-07-19 | Celanese Corporation | Method for providing particulates of liquid crystal polymers and particulates produced therefrom |
| US4410683A (en) * | 1981-12-09 | 1983-10-18 | E. I. Du Pont De Nemours And Company | Aromatic, melt-processible (co)polyesters |
| US4408022A (en) * | 1981-12-15 | 1983-10-04 | Celanese Corporation | Blend of polyalkylene terephthalate and wholly aromatic polyester and process for producing the same |
| US4451611A (en) * | 1981-12-15 | 1984-05-29 | Celanese Corporation | Process for forming blend of polyalkylene terephthalate and wholly aromatic polyester which exhibits an anisotropic melt phase |
| US4424184A (en) | 1982-10-12 | 1984-01-03 | E. I. Du Pont De Nemours & Co. | Acceleration of yarn heat-strengthening process |
| JPS58502227A (ja) * | 1982-01-19 | 1983-12-22 | イ−・アイ・デユポン・デ・ニモアス・アンド・カンパニ− | 糸の熱強化方法の促進 |
| US4772089A (en) * | 1982-04-02 | 1988-09-20 | Polyplastics Co., Ltd. | Optical fiber cable and method for producing same |
| CA1228957A (en) * | 1982-06-21 | 1987-11-10 | Norman S. Anderson | Yarn which exhibits high tenacity comprised of thermotropic liquid crystalline polymer fibers, a reinforcing cord comprised thereof and a process of production thereof |
| US4375530A (en) * | 1982-07-06 | 1983-03-01 | Celanese Corporation | Polyester of 2,6-naphthalene dicarboxylic acid, 2,6-dihydroxy naphthalene, terephthalic acid, and hydroquinone capable of forming an anisotropic melt |
| US4473682A (en) * | 1982-07-26 | 1984-09-25 | Celanese Corporation | Melt processable polyester capable of forming an anisotropic melt comprising a relatively low concentration of 6-oxy-2-naphthoyl moiety, 4-oxybenzoyl moiety, 4,4'-dioxybiphenyl moiety, and terephthaloyl moiety |
| US4522974A (en) * | 1982-07-26 | 1985-06-11 | Celanese Corporation | Melt processable polyester capable of forming an anisotropic melt comprising a relatively low concentration of 6-oxy-2-naphthoyl moiety-4-benzoyl moiety, 1,4-dioxyphenylene moiety, isophthaloyl moiety and terephthaloyl moiety |
| US4468364A (en) * | 1983-04-28 | 1984-08-28 | Celanese Corporation | Process for extruding thermotropic liquid crystalline polymers |
| DE3325705A1 (de) * | 1983-07-16 | 1985-01-24 | Bayer Ag, 5090 Leverkusen | Mesomorphe aromatische polyester mit hoher zaehigkeitund verbesserter schmelzviskositaet, verfahren zu ihrer herstellung und ihre verwendung zur herstellung von formkoerpern, filamenten, fasern und folien |
| US4632798A (en) * | 1983-07-27 | 1986-12-30 | Celanese Corporation | Encapsulation of electronic components with anisotropic thermoplastic polymers |
| DE3338805A1 (de) * | 1983-10-26 | 1985-05-15 | Basf Ag, 6700 Ludwigshafen | Vollaromatische polyester |
| US4742149A (en) * | 1983-11-30 | 1988-05-03 | Dart Industries, Inc. | Production of melt consistent aromatic polyesters |
| JPS60188421A (ja) * | 1984-03-09 | 1985-09-25 | Agency Of Ind Science & Technol | 共重合ポリエステル |
| US6045906A (en) | 1984-03-15 | 2000-04-04 | Cytec Technology Corp. | Continuous, linearly intermixed fiber tows and composite molded article thereform |
| US4719250A (en) * | 1984-06-18 | 1988-01-12 | Hoechst Celanese Corporation | Encapsulation of electronic components |
| DE3480010D1 (en) * | 1984-07-04 | 1989-11-09 | Celanese Corp | Non-woven articles comprised of thermotropic liquid crystal polymer fibers and method of production thereof |
| JPS6197418A (ja) * | 1984-10-18 | 1986-05-15 | Nippon Ester Co Ltd | ポリアリレ−ト繊維 |
| US4673724A (en) * | 1984-12-07 | 1987-06-16 | Toyo Boseki Kabushiki Kaisha | Polymeric whisker and production of the same |
| JPH0635687B2 (ja) * | 1985-12-03 | 1994-05-11 | 日本エステル株式会社 | ポリエステル繊維 |
| DE3609805A1 (de) | 1986-03-22 | 1987-09-24 | Basf Ag | Verfahren zur herstellung von formkoerpern aus fluessig-kristallinen polymeren |
| JPH0713130B2 (ja) * | 1986-04-01 | 1995-02-15 | 三井石油化学工業株式会社 | 芳香族ポリエステル |
| JPH0749472B2 (ja) * | 1986-09-26 | 1995-05-31 | ポリプラスチックス株式会社 | コポリエステルの製造方法 |
| JP2559380B2 (ja) * | 1986-10-22 | 1996-12-04 | ポリプラスチックス株式会社 | 液晶性ポリマ− |
| JP2517568B2 (ja) * | 1986-11-13 | 1996-07-24 | ポリプラスチックス株式会社 | 分子鎖末端が封止された液晶性コポリエステル |
| US4746694A (en) * | 1987-07-06 | 1988-05-24 | Hoechst Celanese Corporation | Melt processable polyester capable of forming an anisotropic melt comprising a relatively low concentration of 6-oxy-2-naphthoyl moiety, 4-oxybenzoyl moiety, 2,6-dioxynaphthalene moiety, and terephthaloyl moiety |
| ATE86266T1 (de) * | 1987-10-05 | 1993-03-15 | Polyplastics Co | Harz mit ausgezeichneter waermebestaendigkeit und anisotropischen eigenschaften in der schmelze. |
| US4891261A (en) * | 1988-02-29 | 1990-01-02 | Aluminum Company Of America | Thermoplastic stock shape and method for making the same |
| JPH0830112B2 (ja) * | 1988-10-24 | 1996-03-27 | ポリプラスチックス株式会社 | 溶融時に光学的異方性を示すポリエステル樹脂及び樹脂組成物 |
| JPH0830111B2 (ja) * | 1988-10-24 | 1996-03-27 | ポリプラスチックス株式会社 | 溶融時に光学的異方性を示すポリエステル樹脂及び樹脂組成物 |
| 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 |
| JP2823873B2 (ja) * | 1988-12-27 | 1998-11-11 | ポリプラスチックス株式会社 | 流動性改良液晶性ポリエステル樹脂組成物 |
| JPH02276819A (ja) * | 1988-12-29 | 1990-11-13 | Kawasaki Steel Corp | 芳香族ポリエステルおよび芳香族ポリエステルアミドならびにそれらを用いた繊維、樹脂組成物 |
| USH1187H (en) | 1989-08-28 | 1993-05-04 | Shell Oil Company | Polymer blends |
| US5393848A (en) * | 1990-01-16 | 1995-02-28 | Hoechst Celanese Corp. | Process for forming improved liquid crystalline polymer blends |
| US5053246A (en) * | 1990-03-30 | 1991-10-01 | The Goodyear Tire & Rubber Company | Process for the surface treatment of polymers for reinforcement-to-rubber adhesion |
| KR930005104B1 (ko) * | 1990-08-30 | 1993-06-15 | 한국과학기술연구원 | 액정 폴리에스테르 펄프상 단섬유 |
| US5135990A (en) * | 1990-10-05 | 1992-08-04 | General Electric Company | Polyetherimide-liquid crystalline polymer blends |
| US5221730A (en) * | 1990-11-16 | 1993-06-22 | Eastman Kodak Company | Polyesters from terephthalic acid, 2,6-naphthalenedicarboxylic acid and hydroquinone |
| US5237038A (en) * | 1990-11-16 | 1993-08-17 | Eastman Kodak Company | Polyesters from terephthalic acid, 2,6-naphthalenedicarboxylic acid, hydroquinone and 4,4'-biphenol |
| KR950001643B1 (ko) * | 1991-08-07 | 1995-02-27 | 한국과학기술연구원 | 현장 복합 성형품 제조용 조성물 및 그 성형품 |
| US5654045A (en) * | 1992-12-21 | 1997-08-05 | Hoechst Celanese Corp. | Multiaxially reinforced LCP sheet |
| CA2263603A1 (en) | 1996-09-11 | 1998-03-19 | Kenneth Earl Stevens | Polymeric multilayer heat exchangers containing a barrier layer |
| WO1998010926A1 (en) | 1996-09-11 | 1998-03-19 | Dupont Canada Inc. | Heat exchangers containing liquid crystalline polymer layers |
| US6036711A (en) * | 1998-02-18 | 2000-03-14 | United States Surgical Corporation | Reusable cannula |
| US6379795B1 (en) | 1999-01-19 | 2002-04-30 | E. I. Du Pont De Nemours And Company | Injection moldable conductive aromatic thermoplastic liquid crystalline polymeric compositions |
| US6364008B1 (en) | 1999-01-22 | 2002-04-02 | E. I. Du Pont De Nemours And Company | Heat exchanger with tube plates |
| WO2000079206A1 (en) | 1999-06-22 | 2000-12-28 | Dupont Canada Inc. | Heat exchanger formed from tubes joined by simultaneous extrusion thermal bonding |
| EP1342045B1 (en) | 2000-10-06 | 2004-08-11 | E.I.Du pont de nemours and company | Heat exchanger made from bendable plastic tubing |
| JP2005518076A (ja) * | 2002-02-13 | 2005-06-16 | デュポン カナダ インコーポレイテッド | 低剪断歪み下の燃料電池セパレータープレートの製造方法 |
| JP2004013054A (ja) | 2002-06-11 | 2004-01-15 | Sumitomo Chem Co Ltd | 高耐熱ラベル |
| US20040113129A1 (en) * | 2002-07-25 | 2004-06-17 | Waggoner Marion G. | Static dissipative thermoplastic polymer composition |
| US20050082720A1 (en) * | 2003-01-23 | 2005-04-21 | Bloom Joy S. | Moldings of liquid crystalline polymer powders |
| US6974606B2 (en) * | 2003-05-23 | 2005-12-13 | Northrop Grumman Corporation | Thermoplastic coating for composite structures |
| CA2538761A1 (en) * | 2005-03-08 | 2006-09-08 | Anthony Joseph Cesaroni | Method for sealing heat exchanger tubes |
| US7547849B2 (en) * | 2005-06-15 | 2009-06-16 | E.I. Du Pont De Nemours And Company | Compositions useful in electronic circuitry type applications, patternable using amplified light, and methods and compositions relating thereto |
| US20080081882A1 (en) * | 2006-10-02 | 2008-04-03 | Dong Tian | Polyester binder for flooring products |
| US8519053B2 (en) * | 2006-10-02 | 2013-08-27 | Armstrong World Industries, Inc. | PVC/polyester binder for flooring |
| US20100184348A1 (en) * | 2006-12-20 | 2010-07-22 | Imerys Pigments, Inc. | Spunlaid Fibers Comprising Coated Calcium Carbonate, Processes For Their Production, and Nonwoven Products |
| EP2150385B8 (en) | 2007-06-03 | 2012-03-21 | Imerys Pigments, Inc. | Spunlaid fibers comprising coated calcium carbonate, processes for their production, and nonwoven products |
| US20090017309A1 (en) * | 2007-07-09 | 2009-01-15 | E. I. Du Pont De Nemours And Company | Compositions and methods for creating electronic circuitry |
| US8475924B2 (en) | 2007-07-09 | 2013-07-02 | E.I. Du Pont De Nemours And Company | Compositions and methods for creating electronic circuitry |
| US20110052913A1 (en) * | 2008-01-21 | 2011-03-03 | Mcamish Larry | Monofilament fibers comprising at least one filler, and processes for their production |
| US20110059287A1 (en) * | 2008-01-21 | 2011-03-10 | Imerys Pigments, Inc. | Fibers comprising at least one filler, processes for their production, and uses thereof |
| US20100035045A1 (en) * | 2008-01-21 | 2010-02-11 | Imerys Pigments, Inc. | Fibers comprising at least one filler and processes for their production |
| JP5520493B2 (ja) | 2008-10-20 | 2014-06-11 | 古河電気工業株式会社 | 多層絶縁電線及びそれを用いた変圧器 |
| US20100193950A1 (en) * | 2009-01-30 | 2010-08-05 | E.I.Du Pont De Nemours And Company | Wafer level, chip scale semiconductor device packaging compositions, and methods relating thereto |
| KR20140117696A (ko) | 2009-09-02 | 2014-10-07 | 후루카와 덴키 고교 가부시키가이샤 | 다층 절연 전선 및 그것을 이용한 변압기 |
| EP2655846A1 (en) | 2010-12-22 | 2013-10-30 | Ticona LLC | High temperature conduit having a complex, three-dimensional configuration |
| US8852730B2 (en) | 2011-08-29 | 2014-10-07 | Ticona Llc | Melt-extruded substrate for use in thermoformed articles |
| KR20140057629A (ko) | 2011-08-29 | 2014-05-13 | 티코나 엘엘씨 | 방향족 아마이드 화합물 |
| WO2013032981A1 (en) | 2011-08-29 | 2013-03-07 | Ticona Llc | High flow liquid crystalline polymer composition |
| US20130053531A1 (en) | 2011-08-29 | 2013-02-28 | Ticona Llc | Method for Minimizing Process Disruptions During Formation of a Liquid Crystalline Polymer |
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| WO2013032975A1 (en) | 2011-08-29 | 2013-03-07 | Ticona Llc | Thermotropic liquid crystalline polymer with improved low shear viscosity |
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| WO2013032974A1 (en) | 2011-08-29 | 2013-03-07 | Ticona Llc | Solid-state polymerization of a liquid crystalline polymer |
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| US9353263B2 (en) | 2011-11-15 | 2016-05-31 | Ticona Llc | Fine pitch electrical connector and a thermoplastic composition for use therein |
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| US8932483B2 (en) | 2011-11-15 | 2015-01-13 | Ticona Llc | Low naphthenic liquid crystalline polymer composition |
| WO2013074475A1 (en) | 2011-11-15 | 2013-05-23 | Ticona Llc | Liquid crystalline polymer composition for high voltage electronic components |
| TW201336665A (zh) | 2011-11-15 | 2013-09-16 | Ticona Llc | 形成液晶熱塑性組合物之方法 |
| TWI464245B (zh) | 2012-06-27 | 2014-12-11 | Ticona Llc | 超低黏度之液晶聚合物組合物 |
| JP6625050B2 (ja) | 2013-06-07 | 2019-12-25 | ティコナ・エルエルシー | 高強度サーモトロピック液晶ポリマー |
| WO2019191580A1 (en) | 2018-03-29 | 2019-10-03 | Atex Technologies, Inc. | Small diameter, high strength, low elongation, creep resistant, abrasion resistant braided structure |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2600376A (en) * | 1949-11-26 | 1952-06-17 | Eastman Kodak Co | Polmesters of hydroxybenzoic acids |
| US3039994A (en) * | 1960-05-11 | 1962-06-19 | Universal Oil Prod Co | Polyesters of hydroxybenzoic acids |
| US3778410A (en) * | 1972-09-28 | 1973-12-11 | Eastman Kodak Co | Process for preparing a final copolyester by reacting a starting polyester with an acyloxy aromatic carboxylic acid |
| US3975487A (en) * | 1973-08-20 | 1976-08-17 | The Carborundum Company | Process for spinning high modulus oxybenzoyl copolyester fibers |
| US3884876A (en) * | 1973-08-31 | 1975-05-20 | Carborundum Co | Partially crosslinked linear aromatic polyesters |
| US3890256A (en) * | 1974-06-07 | 1975-06-17 | Eastman Kodak Co | Copolyester prepared by contacting acyloxy benzoic acid with a polyester of ethylene glycol and dicarboxylic acid |
| US4083829A (en) * | 1976-05-13 | 1978-04-11 | Celanese Corporation | Melt processable thermotropic wholly aromatic polyester |
| US4067852A (en) * | 1976-05-13 | 1978-01-10 | Celanese Corporation | Melt processable thermotropic wholly aromatic polyester containing polybenzoyl units |
-
1978
- 1978-02-15 US US05/877,917 patent/US4184996A/en not_active Expired - Lifetime
- 1978-08-23 CA CA309,912A patent/CA1123993A/en not_active Expired
- 1978-09-05 JP JP10819778A patent/JPS5450594A/ja active Granted
- 1978-09-11 EP EP78300373A patent/EP0001340B1/en not_active Expired
- 1978-09-11 DE DE7878300373T patent/DE2861360D1/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US4184996A (en) | 1980-01-22 |
| EP0001340A1 (en) | 1979-04-04 |
| JPS633891B2 (OSRAM) | 1988-01-26 |
| EP0001340B1 (en) | 1981-11-25 |
| DE2861360D1 (en) | 1982-01-28 |
| JPS5450594A (en) | 1979-04-20 |
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| MKEX | Expiry |