JPH0455210B2 - - Google Patents
Info
- Publication number
- JPH0455210B2 JPH0455210B2 JP58125630A JP12563083A JPH0455210B2 JP H0455210 B2 JPH0455210 B2 JP H0455210B2 JP 58125630 A JP58125630 A JP 58125630A JP 12563083 A JP12563083 A JP 12563083A JP H0455210 B2 JPH0455210 B2 JP H0455210B2
- Authority
- JP
- Japan
- Prior art keywords
- units
- mol
- polyester copolymer
- unit
- 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
Links
- 229920000728 polyester Polymers 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 claims description 2
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 229950011008 tetrachloroethylene Drugs 0.000 claims description 2
- CHAACYSLCZLAEN-UHFFFAOYSA-N 1,1,1,3-tetrafluoropropan-2-one Chemical compound FCC(=O)C(F)(F)F CHAACYSLCZLAEN-UHFFFAOYSA-N 0.000 claims 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 28
- 229920000642 polymer Polymers 0.000 description 26
- 238000010438 heat treatment Methods 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000012965 benzophenone Substances 0.000 description 14
- 239000000835 fiber Substances 0.000 description 14
- 238000006116 polymerization reaction Methods 0.000 description 14
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 13
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 13
- 239000000155 melt Substances 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000004804 winding Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 5
- -1 chloro- Chemical class 0.000 description 5
- 238000002074 melt spinning Methods 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- AJPXTSMULZANCB-UHFFFAOYSA-N chlorohydroquinone Chemical compound OC1=CC=C(O)C(Cl)=C1 AJPXTSMULZANCB-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 2
- 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 2
- 241000790917 Dioxys <bee> Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-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
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 125000004989 dicarbonyl group Chemical group 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000004745 nonwoven fabric Substances 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- BJNWFLGHFAIHAX-UHFFFAOYSA-N (4-acetyloxy-3-chlorophenyl) acetate Chemical compound CC(=O)OC1=CC=C(OC(C)=O)C(Cl)=C1 BJNWFLGHFAIHAX-UHFFFAOYSA-N 0.000 description 1
- AKOGNYJNGMLDOA-UHFFFAOYSA-N (4-acetyloxyphenyl) acetate Chemical compound CC(=O)OC1=CC=C(OC(C)=O)C=C1 AKOGNYJNGMLDOA-UHFFFAOYSA-N 0.000 description 1
- IBFMADKVGRNGDG-UHFFFAOYSA-N 1,3-dichloro-1,1,3,3-tetrafluoropropan-2-one;hydrate Chemical compound O.FC(F)(Cl)C(=O)C(F)(F)Cl IBFMADKVGRNGDG-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 102000002508 Peptide Elongation Factors Human genes 0.000 description 1
- 108010068204 Peptide Elongation Factors Proteins 0.000 description 1
- BSPZSNZSYCFYBF-UHFFFAOYSA-N acetic acid;2-phenylbenzene-1,4-diol Chemical compound CC(O)=O.CC(O)=O.OC1=CC=C(O)C(C=2C=CC=CC=2)=C1 BSPZSNZSYCFYBF-UHFFFAOYSA-N 0.000 description 1
- BBQAATXCGGCSCO-UHFFFAOYSA-N acetic acid;4-hydroxybenzoic acid Chemical compound CC(O)=O.OC(=O)C1=CC=C(O)C=C1 BBQAATXCGGCSCO-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- XCZKKZXWDBOGPA-UHFFFAOYSA-N phenyl-hydroquinone Natural products OC1=CC=C(O)C(C=2C=CC=CC=2)=C1 XCZKKZXWDBOGPA-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical class OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 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
- 239000000126 substance Substances 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- 238000012360 testing method 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
- C08G63/02—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
-
- 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
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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US398563 | 1982-07-15 | ||
| US06/398,563 US4381389A (en) | 1982-07-15 | 1982-07-15 | Optically anisotropic melt forming copolyesters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5924721A JPS5924721A (ja) | 1984-02-08 |
| JPH0455210B2 true JPH0455210B2 (en]) | 1992-09-02 |
Family
ID=23575856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58125630A Granted JPS5924721A (ja) | 1982-07-15 | 1983-07-12 | 光学的異方性をもつ熔融物を生成するポリエステル共重合体 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4381389A (en]) |
| EP (1) | EP0103371B1 (en]) |
| JP (1) | JPS5924721A (en]) |
| CA (1) | CA1192336A (en]) |
| DE (1) | DE3369336D1 (en]) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014065422A1 (ja) | 2012-10-26 | 2014-05-01 | 三菱瓦斯化学株式会社 | ハロゲン化シアンの製造方法、シアン酸エステル化合物及びその製造方法、並びに樹脂組成物 |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4447592A (en) * | 1983-06-13 | 1984-05-08 | E. I. Du Pont De Nemours And Company | Anisotropic melt polyesters of 6-hydroxy-2-naphthoic acid |
| DE3415530A1 (de) * | 1984-04-26 | 1985-10-31 | Bayer Ag, 5090 Leverkusen | Thermotrope aromatische polyester hoher steifigkeit und zaehigkeit, verfahren zu ihrer herstellung und ihre verwendung zur herstellung von formkoerpern, filamenten, fasern und folien |
| US4500699A (en) * | 1984-06-26 | 1985-02-19 | E. I. Du Pont De Nemours And Company | Optically anisotropic melt forming copolyesters |
| EP0166830B1 (en) * | 1984-07-04 | 1989-10-04 | Celanese Corporation | Non-woven articles comprised of thermotropic liquid crystal polymer fibers and method of production thereof |
| JPS6128059A (ja) * | 1984-07-10 | 1986-02-07 | ヘキスト・セラニーズ・コーポレーション | サ−モトロピツク液晶ポリマ−繊維よりなる不織製品およびその製法 |
| DE3427886A1 (de) * | 1984-07-28 | 1986-01-30 | Bayer Ag, 5090 Leverkusen | Thermotrope aromatische polyester mit hoher steifigkeit, verfahren zu ihrer herstellung und ihre verwendung zur herstellung von formkoerpern, filamenten, fasern und folien |
| EP0206023A3 (en) * | 1985-06-17 | 1988-08-10 | Sumitomo Chemical Company, Limited | A method of manufacturing fiber-reinforced composite materials |
| JPH0699876B2 (ja) * | 1985-09-04 | 1994-12-07 | 住友化学工業株式会社 | 高強度ロ−プ |
| US5097001A (en) * | 1988-10-11 | 1992-03-17 | Richard Layton | Hydroquinone poly(iso-terephthalates) containing residues of p-hydroxybenzoic acid |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US4226970A (en) * | 1979-07-23 | 1980-10-07 | E. I. Du Pont De Nemours And Company | Polyesters derived from diketodiols and aromatic dicarboxylic acids and filaments thereof |
| US4269965A (en) * | 1979-09-17 | 1981-05-26 | E. I. Du Pont De Nemours And Company | Aromatic polyester which forms optically anisotropic melts and filaments thereof |
| US4232143A (en) * | 1979-09-17 | 1980-11-04 | E. I. Du Pont De Nemours And Company | Polyester which exhibits anisotropy in the melt containing p-oxybenzoyl units and 4,4'-dioxybenzophenone units or methyl and chloro derivatives thereof |
| US4232144A (en) * | 1979-09-17 | 1980-11-04 | E. I. Du Pont De Nemours And Company | Polyester which exhibits anisotropy in the melt containing p-oxybenzoyl units and 4-oxy-3'-carbonylbenzophenone units or methyl and chloro derivatives of said units |
| US4335232A (en) * | 1981-07-07 | 1982-06-15 | E. I. Du Pont De Nemours And Company | Optically anisotropic melt forming polyesters |
-
1982
- 1982-07-15 US US06/398,563 patent/US4381389A/en not_active Expired - Lifetime
-
1983
- 1983-07-12 JP JP58125630A patent/JPS5924721A/ja active Granted
- 1983-07-14 DE DE8383304097T patent/DE3369336D1/de not_active Expired
- 1983-07-14 CA CA000432421A patent/CA1192336A/en not_active Expired
- 1983-07-14 EP EP83304097A patent/EP0103371B1/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014065422A1 (ja) | 2012-10-26 | 2014-05-01 | 三菱瓦斯化学株式会社 | ハロゲン化シアンの製造方法、シアン酸エステル化合物及びその製造方法、並びに樹脂組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5924721A (ja) | 1984-02-08 |
| US4381389A (en) | 1983-04-26 |
| EP0103371B1 (en) | 1987-01-21 |
| EP0103371A1 (en) | 1984-03-21 |
| DE3369336D1 (en) | 1987-02-26 |
| CA1192336A (en) | 1985-08-20 |
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