DE2228609C2 - Biphenyloxybenzoesäure, deren Säurehalogenide und C↓1↓↓-↓↓3↓-Alkylester und ein Verfahren zu ihrer Herstellung - Google Patents
Biphenyloxybenzoesäure, deren Säurehalogenide und C↓1↓↓-↓↓3↓-Alkylester und ein Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2228609C2 DE2228609C2 DE2228609A DE2228609A DE2228609C2 DE 2228609 C2 DE2228609 C2 DE 2228609C2 DE 2228609 A DE2228609 A DE 2228609A DE 2228609 A DE2228609 A DE 2228609A DE 2228609 C2 DE2228609 C2 DE 2228609C2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- biphenyloxybenzoic
- preparation
- alkyl esters
- monomers
- 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
- 239000002253 acid Substances 0.000 title claims description 10
- QRCYYYQQMFCBHX-UHFFFAOYSA-N 2-(2-phenylphenoxy)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1C1=CC=CC=C1 QRCYYYQQMFCBHX-UHFFFAOYSA-N 0.000 title claims description 9
- 150000004820 halides Chemical class 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000000178 monomer Substances 0.000 description 16
- 229920000642 polymer Polymers 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 229920001470 polyketone Polymers 0.000 description 10
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical group C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical group CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 4
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000008378 aryl ethers Chemical class 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000009413 insulation Methods 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000010751 Ullmann type reaction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- -1 p-biphenylylbenzoyl Chemical group 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- VIGAGZWJPRGWLQ-UHFFFAOYSA-N 1-phenyl-2-phenylmethoxybenzene Chemical compound C=1C=CC=CC=1COC1=CC=CC=C1C1=CC=CC=C1 VIGAGZWJPRGWLQ-UHFFFAOYSA-N 0.000 description 1
- QSBDJCHYJZOIPJ-UHFFFAOYSA-N 2-(2-phenylphenoxy)benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1OC1=CC=CC=C1C1=CC=CC=C1 QSBDJCHYJZOIPJ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- YRLSATFFDLKHJM-UHFFFAOYSA-N 4-(4-phenylphenoxy)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CC=C(C=2C=CC=CC=2)C=C1 YRLSATFFDLKHJM-UHFFFAOYSA-N 0.000 description 1
- BICYPRAUNKSOIX-UHFFFAOYSA-N 4-(4-phenylphenoxy)benzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1OC1=CC=C(C=2C=CC=CC=2)C=C1 BICYPRAUNKSOIX-UHFFFAOYSA-N 0.000 description 1
- ZQWOMUCIRZYMCI-UHFFFAOYSA-N 4-ethyl-2-(2-phenylphenoxy)benzoic acid Chemical compound CCC1=CC=C(C(O)=O)C(OC=2C(=CC=CC=2)C=2C=CC=CC=2)=C1 ZQWOMUCIRZYMCI-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000009102 absorption Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- UBXYXCRCOKCZIT-UHFFFAOYSA-N biphenyl-3-ol Chemical group OC1=CC=CC(C=2C=CC=CC=2)=C1 UBXYXCRCOKCZIT-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- ZBYYWKJVSFHYJL-UHFFFAOYSA-L cobalt(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Co+2].CC([O-])=O.CC([O-])=O ZBYYWKJVSFHYJL-UHFFFAOYSA-L 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000010932 ethanolysis reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- FGEFZOKTQYNXIJ-UHFFFAOYSA-N ethyl 2-(2-phenylphenoxy)benzoate Chemical compound CCOC(=O)C1=CC=CC=C1OC1=CC=CC=C1C1=CC=CC=C1 FGEFZOKTQYNXIJ-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- LPIAMYJLLVJEQN-UHFFFAOYSA-N methyl 2-(2-phenylphenoxy)benzoate Chemical compound COC(=O)C1=CC=CC=C1OC1=CC=CC=C1C1=CC=CC=C1 LPIAMYJLLVJEQN-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
- B29C48/15—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor incorporating preformed parts or layers, e.g. extrusion moulding around inserts
-
- 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/127—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from carbon dioxide, carbonyl halide, carboxylic acids or their derivatives
-
- 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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/20—Polysulfones
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/307—Other macromolecular compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
- B29C48/03—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor characterised by the shape of the extruded material at extrusion
- B29C48/05—Filamentary, e.g. strands
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
- B29C48/03—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor characterised by the shape of the extruded material at extrusion
- B29C48/06—Rod-shaped
Landscapes
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Mechanical Engineering (AREA)
- Engineering & Computer Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyethers (AREA)
- Organic Insulating Materials (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11582471A | 1971-02-16 | 1971-02-16 | |
| US21846672A | 1972-01-17 | 1972-01-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2228609A1 DE2228609A1 (de) | 1973-12-13 |
| DE2228609C2 true DE2228609C2 (de) | 1984-10-31 |
Family
ID=26813605
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2228609A Expired DE2228609C2 (de) | 1971-02-16 | 1972-02-14 | Biphenyloxybenzoesäure, deren Säurehalogenide und C↓1↓↓-↓↓3↓-Alkylester und ein Verfahren zu ihrer Herstellung |
| DE2206836A Expired DE2206836C2 (de) | 1971-02-16 | 1972-02-14 | Polyketone und Verfahren zu ihrer Herstellung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2206836A Expired DE2206836C2 (de) | 1971-02-16 | 1972-02-14 | Polyketone und Verfahren zu ihrer Herstellung |
Country Status (10)
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1470049A (en) * | 1973-03-21 | 1977-04-14 | Rachem Corp | Splicing method and heat-recoverable article |
| EP0031198B2 (en) * | 1979-12-14 | 1992-11-04 | Imperial Chemical Industries Plc | Compositions of aromatic polyetherketones and glass and/or carbon fibres |
| DE3040849A1 (de) * | 1980-10-30 | 1982-06-09 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von diphenylaethern |
| US4359501A (en) | 1981-10-28 | 1982-11-16 | Albany International Corp. | Hydrolysis resistant polyaryletherketone fabric |
| US4698393A (en) * | 1983-03-31 | 1987-10-06 | Raychem Corporation | Preparation of poly(arylene ether ketones) |
| JPH0680113B2 (ja) * | 1983-03-31 | 1994-10-12 | レイケム・コーポレイション | 芳香族ポリマ−の製法 |
| US4709007A (en) * | 1983-03-31 | 1987-11-24 | Raychem Corporation | Preparation of aromatic polymers |
| US4721771A (en) * | 1983-03-31 | 1988-01-26 | Raychem Corporation | Preparation of aromatic polymers |
| US4912195A (en) * | 1983-03-31 | 1990-03-27 | Raychem Corporation | Preparation of aromatic polymers using a specified quantity of Lewis acid |
| US4879366A (en) * | 1983-03-31 | 1989-11-07 | Raychem Corporation | Preparation of aromatic oligomers |
| US4820571A (en) * | 1983-07-12 | 1989-04-11 | Asten Group, Inc. | High temperature industrial fabrics |
| GB8319510D0 (en) * | 1983-07-19 | 1983-08-17 | Bicc Plc | Insulated wires and cables |
| US4650228A (en) * | 1983-09-14 | 1987-03-17 | Raychem Corporation | Heat-recoverable coupling assembly |
| CA1248799A (en) * | 1984-02-23 | 1989-01-17 | Asten, Inc. | Abrasion and hydrolysis resistant joining wire and coil material for fabric seams |
| GB2190041A (en) * | 1986-03-11 | 1987-11-11 | Raychem Ltd | Reinforced polymer composite |
| US4841013A (en) * | 1986-09-18 | 1989-06-20 | Raychem Limited | Preparation of poly(arylene ether ketones) |
| GB8623511D0 (en) * | 1986-09-30 | 1986-11-05 | Raychem Ltd | Arylene cligomers |
| GB8725886D0 (en) * | 1987-11-04 | 1987-12-09 | Raychem Ltd | Poly(ar-lene ether ketones) |
| DE3829520A1 (de) * | 1988-08-31 | 1990-03-01 | Basf Ag | Verfahren zur herstellung von polyarylenetherketonen |
| JP6587042B1 (ja) | 2018-01-22 | 2019-10-09 | Dic株式会社 | ポリアリーレンエーテルケトン樹脂及びその製造方法、並びに成形品 |
-
1972
- 1972-02-14 DE DE2228609A patent/DE2228609C2/de not_active Expired
- 1972-02-14 DE DE2206836A patent/DE2206836C2/de not_active Expired
- 1972-02-15 IL IL38769A patent/IL38769A/xx unknown
- 1972-02-15 GB GB694772A patent/GB1383393A/en not_active Expired
- 1972-02-15 ES ES399817A patent/ES399817A1/es not_active Expired
- 1972-02-16 CH CH219972A patent/CH572952A5/xx not_active IP Right Cessation
- 1972-02-16 JP JP1631872A patent/JPS56451B1/ja active Pending
- 1972-02-16 BE BE779458A patent/BE779458A/xx not_active IP Right Cessation
- 1972-02-16 SE SE7201872A patent/SE411910B/xx unknown
- 1972-02-16 IT IT20630/72A patent/IT960659B/it active
- 1972-02-16 CA CA134,801A patent/CA1014696A/en not_active Expired
-
1975
- 1975-11-28 SE SE7513415A patent/SE411911B/sv not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| ES399817A1 (es) | 1975-06-16 |
| BE779458A (fr) | 1972-08-16 |
| CH572952A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-02-27 |
| SE411910B (sv) | 1980-02-11 |
| GB1383393A (en) | 1974-02-12 |
| IL38769A (en) | 1975-11-25 |
| CA1014696A (en) | 1977-07-26 |
| DE2206836A1 (de) | 1972-12-14 |
| DE2206836C2 (de) | 1983-03-17 |
| SE411911B (sv) | 1980-02-11 |
| DE2228609A1 (de) | 1973-12-13 |
| JPS56451B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-01-08 |
| IT960659B (it) | 1973-11-30 |
| IL38769A0 (en) | 1972-05-30 |
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