JPS6333490B2 - - Google Patents
Info
- Publication number
- JPS6333490B2 JPS6333490B2 JP54500779A JP50077979A JPS6333490B2 JP S6333490 B2 JPS6333490 B2 JP S6333490B2 JP 54500779 A JP54500779 A JP 54500779A JP 50077979 A JP50077979 A JP 50077979A JP S6333490 B2 JPS6333490 B2 JP S6333490B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- molecular weight
- temperature
- copolyester
- acyloxybenzoic
- 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
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 18
- 229920001634 Copolyester Polymers 0.000 description 16
- 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 description 12
- 229920000728 polyester Polymers 0.000 description 12
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 7
- 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 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000003856 thermoforming Methods 0.000 description 4
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 238000003490 calendering Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- DZVDHXPXHBVBNZ-UHFFFAOYSA-N (4-acetyloxy-3-phenylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(OC(C)=O)C(C=2C=CC=CC=2)=C1 DZVDHXPXHBVBNZ-UHFFFAOYSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- -1 aromatic dicarboxylic acids Chemical class 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- UABHETFCVNRGNL-UHFFFAOYSA-N 2-butoxybenzoic acid Chemical compound CCCCOC1=CC=CC=C1C(O)=O UABHETFCVNRGNL-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- RYAQFHLUEMJOMF-UHFFFAOYSA-N 4-phenoxybenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CC=CC=C1 RYAQFHLUEMJOMF-UHFFFAOYSA-N 0.000 description 1
- MQZBJHMHKZVYHB-UHFFFAOYSA-N 4-propanoylbenzoic acid Chemical compound CCC(=O)C1=CC=C(C(O)=O)C=C1 MQZBJHMHKZVYHB-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical class C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 238000011282 treatment Methods 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
- C08G63/60—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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Artificial Filaments (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US90336978A | 1978-05-05 | 1978-05-05 | |
| US05/971,987 US4242496A (en) | 1978-12-21 | 1978-12-21 | Liquid crystal copolyesters containing phenylhydroquinone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55500215A JPS55500215A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-04-10 |
| JPS6333490B2 true JPS6333490B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-07-05 |
Family
ID=27129360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP54500779A Expired JPS6333490B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-05-05 | 1979-05-02 |
Country Status (3)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4529565A (en) * | 1983-08-31 | 1985-07-16 | Asahi Kasei Kogyo Kabushiki Kaisha | Polyester of substituted or unsubstituted phenoxyhydroquinone |
| US4536562A (en) * | 1985-01-04 | 1985-08-20 | Monsanto Company | Liquid crystalline polyesters |
| DE3517948A1 (de) * | 1985-05-18 | 1986-11-20 | Bayer Ag, 5090 Leverkusen | Thermotrope aromatische polyester mit hervorragenden mechanischen eigenschaften und guter verarbeitbarkeit, verfahren zu ihrer herstellung und ihre verwendung zur herstellung von formkoerpern, filamenten, fasern und folien |
| JPH01272630A (ja) * | 1988-04-26 | 1989-10-31 | Toray Ind Inc | 芳香族ポリエステル |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL129038C (nl) * | 1960-06-01 | 1970-01-15 | Gen Electric | Werkwijze ter bereiding van lineaire polyesters |
| US3637595A (en) * | 1969-05-28 | 1972-01-25 | Steve G Cottis | P-oxybenzoyl copolyesters |
| 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 |
| PH15509A (en) * | 1974-05-10 | 1983-02-03 | Du Pont | Improvements in an relating to synthetic polyesters |
| US4064108A (en) * | 1974-10-04 | 1977-12-20 | Teijin Limited | Novel polyesters prepared from mixture of hydroquinone and bisphenols |
| US4066620A (en) * | 1975-04-29 | 1978-01-03 | E. I. Du Pont De Nemours And Company | Copolyester capable of forming anisotropic melt and shaped articles thereof |
| US4075262A (en) * | 1975-08-12 | 1978-02-21 | E. I. Du Pont De Nemours And Company | Copolyesters capable of forming an anisotropic melt |
| 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 |
| US4159365A (en) * | 1976-11-19 | 1979-06-26 | E. I. Du Pont De Nemours And Company | Polyphenyl-1,4-phenylene terephthalates and fibers therefrom |
| 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 |
| US4140846A (en) * | 1978-05-04 | 1979-02-20 | Eastman Kodak Company | Liquid crystal copolyesters containing 4-carboxybenzenepropionic acid |
| US4153779A (en) * | 1978-06-26 | 1979-05-08 | Eastman Kodak Company | Liquid crystal copolyester containing a substituted phenylhydroquinone |
-
1979
- 1979-05-02 WO PCT/US1979/000289 patent/WO1979001034A1/en unknown
- 1979-05-02 JP JP54500779A patent/JPS6333490B2/ja not_active Expired
- 1979-12-04 EP EP19790900502 patent/EP0018973A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| WO1979001034A1 (en) | 1979-11-29 |
| JPS55500215A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-04-10 |
| EP0018973A1 (en) | 1980-11-26 |
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