CN108456303B - Bio-based polyarylether resin containing furan ring structure and preparation method thereof - Google Patents
Bio-based polyarylether resin containing furan ring structure and preparation method thereof Download PDFInfo
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 229920005989 resin Polymers 0.000 title claims abstract description 38
- 239000011347 resin Substances 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 229920000090 poly(aryl ether) Polymers 0.000 title claims abstract description 9
- 229920006260 polyaryletherketone Polymers 0.000 claims abstract description 27
- 239000000178 monomer Substances 0.000 claims abstract description 23
- DNXDYHALMANNEJ-UHFFFAOYSA-N furan-2,3-dicarboxylic acid Chemical compound OC(=O)C=1C=COC=1C(O)=O DNXDYHALMANNEJ-UHFFFAOYSA-N 0.000 claims abstract description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 16
- 238000001035 drying Methods 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 238000009835 boiling Methods 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- 239000012043 crude product Substances 0.000 claims description 7
- 239000000047 product Substances 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 239000011261 inert gas Substances 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000003880 polar aprotic solvent Substances 0.000 claims description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 239000002841 Lewis acid Substances 0.000 claims description 4
- 238000007664 blowing Methods 0.000 claims description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 150000007517 lewis acids Chemical class 0.000 claims description 4
- 239000012046 mixed solvent Substances 0.000 claims description 4
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical group O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 230000002194 synthesizing effect Effects 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- 229910015900 BF3 Inorganic materials 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 2
- 229910052786 argon Inorganic materials 0.000 claims description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052734 helium Inorganic materials 0.000 claims description 2
- 239000001307 helium Substances 0.000 claims description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 2
- 239000011968 lewis acid catalyst Substances 0.000 claims description 2
- 238000003760 magnetic stirring Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 238000000967 suction filtration Methods 0.000 claims description 2
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 claims description 2
- 238000002061 vacuum sublimation Methods 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 7
- 239000002585 base Substances 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 10
- 239000003208 petroleum Substances 0.000 abstract description 9
- 229920006351 engineering plastic Polymers 0.000 abstract description 3
- LSQARZALBDFYQZ-UHFFFAOYSA-N 4,4'-difluorobenzophenone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 LSQARZALBDFYQZ-UHFFFAOYSA-N 0.000 abstract description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 abstract 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 5
- 238000007334 copolymerization reaction Methods 0.000 description 4
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- IAKOZHOLGAGEJT-UHFFFAOYSA-N 1,1,1-trichloro-2,2-bis(p-methoxyphenyl)-Ethane Chemical compound C1=CC(OC)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(OC)C=C1 IAKOZHOLGAGEJT-UHFFFAOYSA-N 0.000 description 1
- YWFPGFJLYRKYJZ-UHFFFAOYSA-N 9,9-bis(4-hydroxyphenyl)fluorene Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 YWFPGFJLYRKYJZ-UHFFFAOYSA-N 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical compound C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
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- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
- C08G65/4012—Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
- C08G65/4006—(I) or (II) containing elements other than carbon, oxygen, hydrogen or halogen as leaving group (X)
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
- C08G65/4012—Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
- C08G65/4031—(I) or (II) containing nitrogen
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
- C08G65/4093—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group characterised by the process or apparatus used
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- Chemical & Material Sciences (AREA)
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Abstract
The invention discloses a furan ring structure-containing bio-based polyarylether resin and a preparation method thereof, belonging to the technical field of polymer science. The furan ring structure-containing bio-based monomer furan-2, 5-di (4-fluorophenyl) ketone (BFBF) prepared by using bio-based derivative Furan Dicarboxylic Acid (FDAC) is subjected to nucleophilic substitution reaction with one or more of dihydric phenol monomer and dihalobenzophenone monomer to prepare the furan ring structure-containing bio-based homopolymerized or copolymerized polyaryletherketone resin. The biobased polyaryletherketone resin is introduced into the field of special engineering plastics, so that the variety of the polyaryletherketone resin is enriched, and the petroleum crisis is effectively coped with.
Description
Technical Field
The invention belongs to the technical field of polymer science, relates to a novel polyarylether resin and a preparation method thereof, and particularly relates to a furan ring structure-containing bio-based polyarylether resin and a preparation method thereof.
Background
The polyaryletherketone resin is a novel high-temperature-resistant high-performance engineering plastic, has the advantages of high heat-resistant grade, excellent mechanical property, electrical property and radiation resistance, chemical resistance, fatigue resistance, impact resistance, creep resistance, wear resistance, flame retardance and the like, and is widely applied to many high and new technical fields of aviation, electronic information, energy and the like. However, conventional polyaryletherketone resins have been developed based on non-renewable petroleum resources. With the annual increase of the crude oil consumption in the world and the gradual decline of the petroleum reserves, the shortage of petroleum resources is bound to become the limitation of the further development of high-performance engineering plastic polyaryletherketone resin. Therefore, the research and development of the bio-based polyaryletherketone resin have very important time significance and will become the inevitable trend of future development.
Furan dicarboxylic acid (FDCA) is a biobased diacid [ LewkowskiJ. Synthesis, chemistry and applications of 5-Hydroxymethyl-furfuel and Its derivatives chemistry Chemform.2001, 34(2):37 ], similar in structure to terephthalic acid (PTA), prepared by catalytic oxidation of the biomass derivative 5-Hydroxymethylfurfural (HMF) [ Willem P.Dijkman, Daphene E.Groothuis, MarcoW.Fraje.AngewamInt Ed.2014,53(25): 6515-. With the increasing maturity of bio-based furandicarboxylic acid production technologies, numerous studies have been attempted using furandicarboxylic acid instead of terephthalic acid, such as polyesters containing furan ring structures (PEF, PPF, PBF) [ Knoop R JI, Vogelzang W, Haveren J.journal of Polymer Science Part A: Polymer chemistry.2013,51(19): 4191) 4199, epoxy resins [ Deng J, Liu X, Li C, Jiang Y, Zhu J.RSC adv.2015,5(21): 30 15939], polyimides, and the like. The research results show that the introduction of the furan ring structure does not reduce the performance of the material, and the furan ring structure is obviously improved in some aspects.
The subject group is dedicated to the research of petroleum-based polyaryletherketone resin, develops a series of polyaryletherketone resin with excellent performance, and is widely applied to the industries of aerospace, electronic and electrical, petroleum exploitation and the like. In view of the above, the invention starts from furandicarboxylic acid, prepares bio-based and dihalo-benzophenone monomers containing furan ring structures, creatively utilizes the bio-based dihalo-benzophenone monomer containing furan ring structures furan-2, 5-bis (4-fluorophenyl) ketone (BFBF), develops a class of bio-based homopolymerization (or copolymerization) polyaryletherketone resin containing furan ring structures, and aims to prepare polyaryletherketone resin by using bio-based monomers instead of petroleum-based monomers so as to deal with petroleum crisis and environmental problems. At present, no public report is found.
Disclosure of Invention
The invention relates to a furan ring structure-containing bio-based polyaryletherketone resin and a preparation method thereof. The preparation method comprises the step of carrying out nucleophilic polycondensation reaction on furan-2, 5-di (4-fluorophenyl) ketone (BFBF) as a biological group monomer containing a furan ring structure and one or more of a dihydric phenol monomer and dihalobenzophenone to prepare the polyaryletherketone resin containing the furan ring structure and the biological group homopolymerization (or copolymerization).
The technical scheme of the invention is as follows:
a furan ring structure-containing bio-based polyarylether resin has the following chemical structure:
wherein m is more than or equal to 1, and n is more than or equal to 0;
one or a combination of two or more of them; wherein, R, R1、R2、R3、R4、R5、R6、R7、R8The structure is as follows: H. f, Cl, Br, I, CN, NH2、Cr+1H2r+2、CrH2r+1、CrH2r+1COOH、OCrH2r+1、CF3、One or more than two of the (a) and (b) are mixed, and r is more than or equal to 1; r, R1、R2、R3、R4、R5、R6、R7And R8The same or different;
A preparation method of furan ring structure-containing bio-based polyarylether resin comprises the following polymerization reaction formula and steps:
wherein m is more than or equal to 1, n is more than or equal to 0, and X is F, Cl, Br or I;
one or a combination of two or more of them; wherein, R, R1、R2、R3、R4、R5、R6、R7、R8The structure is as follows: H. f, Cl, Br, I, CN, NH2、Cr+1H2r+2、CrH2r+1、CrH2r+1COOH、OCrH2r+1、CF3、One or more than two of the (a) and (b) are mixed, and r is more than or equal to 1; r, R1、R2、R3、R4、R5、R6、R7And R8The same or different;
the specific synthesis steps are as follows:
under the protection of inert gas, containing furan ring structureOf a dihalogen monomer ofStructural dihydric phenol monomer, containingMixing a structural double-halogen monomer with alkali, adding a strong polar aprotic solvent and an azeotropic solvent, carrying out water treatment on a reaction system at the temperature of 110-150 ℃, removing the azeotropic solvent after reacting for 0.5-3 h, heating the reaction system to 160-200 ℃, reacting for 5-10 h, slowly pouring a viscous solution into a settling agent to obtain a fibrous substance, filtering, boiling for 10-24 h with boiling water, drying at the temperature of 100-150 ℃ for 10-24 h, and drying at the temperature of 90-150 ℃ under a vacuum condition to constant weight to obtain a crude polyaryletherketone resin product containing the furan ring structure bio-group homopolymerization or copolymerization; dissolving a crude polyaryletherketone resin product in a good solvent, wherein the mass ratio of the crude product to the good solvent is 1: 5-1: 35, filtering, settling filtrate in a settling agent, and sequentially filtering, drying by blowing and drying in vacuum to obtain the refined furan ring structure-containing bio-based polyaryletherketone resin;
wherein the molar ratio of the phenolic hydroxyl group to the halogen is 1: 0.9-1: 1.1, and the molar ratio of the alkali to the phenolic hydroxyl group is 1: 1.2-1: 2.2; the volume ratio of the azeotropic solvent to the mixed solvent is 1: 1-1: 3.
The structure containing furan ringThe reaction formula and the preparation method of the double-halogen monomer are as follows:
wherein, X has the structure: F. one of Cl, Br and I;
firstly, synthesizing a furan diformyl chloride intermediate, namely adding bio-based furan dicarboxylic acid and thionyl chloride into a reaction vessel with magnetic stirring according to the mass ratio of 0.2: 1-1: 1, and simultaneously adding a small amount of strong polar aprotic solvent DMF (1% of the volume of the thionyl chloride), wherein the reaction temperature is as follows: 60-100 ℃, reaction time: 2-6 hours. After the reaction is finished, cooling the system to room temperature, removing redundant thionyl chloride, and carrying out vacuum sublimation to obtain a white furan diformyl chloride FDCC crystal;
and secondly, under the protection of inert gas, taking the furan ring structure-containing bio-based intermediate FDCC and fluorobenzene as raw materials, taking Lewis acid as a catalyst, and reacting in a low-boiling-point organic solvent to prepare the target monomer. Wherein the mol ratio of FDCC to fluorobenzene is 1: 2-1: 5, the volume ratio of the low-boiling-point organic solvent to FDCC is 1: 3-1: 5, and the mol ratio of the Lewis acid catalyst to FDCC is 1: 2-1: 5; the reaction temperature is 25-100 ℃, and the reaction time is 10-24 h; after the reaction is finished, the mixture is settled in a settling agent, and the furan ring structure-containing bio-based dihalobenzophenone monomer BFBF is obtained after suction filtration, purification and drying.
Wherein, the inert gas is one of nitrogen, argon and helium.
The Lewis acid is one or the mixture of more than two of boron trichloride, boron tribromide, boron trifluoride and aluminum trichloride.
The low boiling point organic solvent is one or the mixture of more than two of chloroform, dichloromethane, dichloroethane and acetonitrile.
The alkali is one or more of potassium carbonate, cesium carbonate, sodium hydroxide and potassium hydroxide.
The strong polar aprotic solvent is one or a mixture of more than two of N, N-dimethylformamide, N-dimethylacetamide, dimethyl sulfoxide, N-methylpyrrolidone and sulfolane.
The azeotropic solvent is one or more of toluene, xylene and chlorobenzene.
The good solvent is one or a mixture of more than two of N, N-dimethylformamide, N-dimethylacetamide, dimethyl sulfoxide, N-methylpyrrolidone, sulfolane and chloroform.
The settling agent is one or more of methanol, ethanol, isopropanol, acetone and water.
The invention has the beneficial effects that: the bio-based monomer furan dicarboxylic acid is used for designing and synthesizing a bio-based dihalobenzophenone monomer containing a furan ring structure, and then a series of excellent-performance bio-based homopolymerization (or copolymerization) polyaryletherketone resins containing the furan ring structure are prepared. The resin not only effectively deals with the petroleum crisis, but also can be regulated and controlled to obtain the target resin with high temperature resistance, dissolubility, easy processing and excellent mechanical property so as to meet the actual requirement.
Drawings
FIG. 1 is a 1H-NMR spectrum of a furan ring structure-containing bio-based polyaryletherketone resin PFBEK.
FIG. 2 is a 1H-NMR spectrum of a furan ring structure-containing bio-based polyaryletherketone resin PFBEK.
FIG. 3 is FT IR spectrum of furan ring structure-containing bio-based polyaryletherketone resins PFBEK and PFDEK.
Detailed Description
The following examples further illustrate the preparation method and properties of the furan ring structure-containing bio-based polyaryletherketone resin of the present invention, but do not represent the limitation of the present patent.
EXAMPLE 1 preparation of PFBEK
Under the protection of nitrogen atmosphere, a furan ring structure-containing bio-based monomer BFBF (10mmol,3.1227g), 9, 9-bis (4-hydroxyphenyl) fluorene BPF (10mmol,3.5042g) and anhydrous potassium carbonate K are added into a three-neck flask with mechanical stirring2CO3(14mmol,1.9023g) was dissolved in 4ml of sulfolaneReacting 1ml of N-methyl pyrrolidone and 10ml of toluene in a mixed solvent at 125-160 ℃ for 4h, evaporating the toluene in the mixed system, then heating to 195 ℃ for reaction for 10h, pouring the viscous solution into hot water to obtain a white fibrous polymer, boiling the fibrous polymer in boiling water for 8-12 h, and drying to constant weight to obtain a white furan ring structure-containing bio-based polyaryletherketone resin PFBEK crude product. Dissolving the crude product in chloroform according to a certain proportion, filtering, settling the filtered solution in absolute ethyl alcohol, and then sequentially filtering, drying by blowing and drying in vacuum to obtain the refined target product PFBEK with the yield of 99.9%. The nuclear magnetic and infrared characteristics of PFBEK are shown in the attached figures 1 and 2, and the heat resistance characteristics are shown in the table 1.
The structural formula is as follows:
EXAMPLE 2 preparation of polymer PFDEK
Under the protection of nitrogen atmosphere, a furan ring structure-containing bio-based monomer BFBF (10mmol,3.1227g), phthalazinone biphenyl DHPZ (10mmol,2.3824g) and anhydrous potassium carbonate K are added into a three-neck flask with mechanical stirring2CO3(14mmol,1.9023g) is dissolved in a mixed solvent of 3ml of sulfolane, 2ml of N, N-dimethylacetamide and 10ml of toluene, the mixture reacts for 4 hours at 125-160 ℃, the toluene in the mixed system is evaporated, then the temperature is raised to 195 ℃ for reaction for 10 hours, finally the viscous solution is poured into hot water to obtain a white fibrous polymer, the fibrous polymer is boiled by boiling water for 8-12 hours, and then the fibrous polymer is dried to constant weight to obtain a white crude product of the furan ring structure-containing bio-based polyaryletherketone resin PFDEK. And dissolving the crude product in chloroform according to a certain proportion, filtering, settling the filtered solution in absolute ethyl alcohol, and sequentially filtering, drying by blowing and drying in vacuum to obtain a refined target product PFDEK with the yield of 99.9%. The nuclear magnetic and infrared characterization of PFDEK is shown in fig. 3 and fig. 2, and the thermal performance test data is shown in table 1.
TABLE 1 thermal performance test of furan ring structure-containing bio-based polyaryletherketone resin PFBEK and PFDEK
And (6) obtaining the result.
Claims (10)
2. A preparation method of furan ring structure-containing bio-based polyarylether resin is characterized by comprising the following polymerization reaction formula and steps:
wherein m is more than or equal to 1, and X is any one of F, Cl, Br and I;
the specific synthesis steps are as follows:
under the protection of inert gas, containing furan ring structureOf a dihalogen monomer ofMixing a structural dihydric phenol monomer with alkali, adding a strong polar aprotic solvent and an azeotropic solvent, carrying out water treatment on a reaction system at the temperature of 110-150 ℃, removing the azeotropic solvent after reacting for 0.5-3 h, heating the reaction system to 160-200 ℃, reacting for 5-10 h, slowly pouring a viscous solution into a settling agent to obtain a fibrous substanceFiltering, boiling in boiling water for 10-24 h, drying at 100-150 ℃ for 10-24 h, and drying at 90-150 ℃ under vacuum condition to constant weight to obtain a furan ring structure-containing bio-based copolymerized polyaryletherketone resin crude product; dissolving a crude polyaryletherketone resin product in a good solvent, wherein the mass ratio of the crude product to the good solvent is 1: 5-1: 35, filtering, settling filtrate in a settling agent, and sequentially filtering, drying by blowing and drying in vacuum to obtain the refined furan ring structure-containing bio-based polyaryletherketone resin;
wherein the molar ratio of the phenolic hydroxyl group to the halogen is 1: 0.9-1: 1.1, the molar ratio of the alkali to the phenolic hydroxyl group is 1: 1.2-1: 2.2, and the volume ratio of the azeotropic solvent to the mixed solvent is 1: 1-1: 3.
firstly, synthesizing a furan diformyl chloride intermediate: adding bio-based furandicarboxylic acid and thionyl chloride into a reaction container with magnetic stirring according to the mass ratio of 0.2: 1-1: 1, and simultaneously adding a strong polar aprotic solvent DMF which is 1% of the volume of the thionyl chloride, wherein the reaction temperature is as follows: 60-100 ℃, reaction time: 2-6 hours; after the reaction is finished, cooling the system to room temperature, removing redundant thionyl chloride, and carrying out vacuum sublimation to obtain a white furcellstructured bio-based intermediate furyldimethylchloride FDCC crystal;
under the protection of inert gas, taking a furan ring structure-containing bio-based intermediate FDCC and fluorobenzene as raw materials, taking Lewis acid as a catalyst, and reacting in a low-boiling-point organic solvent to prepare a target monomer; wherein the mol ratio of FDCC to fluorobenzene is 1: 2-1: 5, the volume ratio of the low-boiling-point organic solvent to FDCC is 1: 3-1: 5, and the mol ratio of the Lewis acid catalyst to FDCC is 1: 2-1: 5; the reaction temperature is 25-100 ℃, and the reaction time is 10-24 h; after the reaction is finished, the product is settled in a settling agent, and is subjected to suction filtration, purification and drying to obtain the product.
5. The method according to claim 4, wherein the base is one or more of potassium carbonate, cesium carbonate, sodium hydroxide, and potassium hydroxide.
6. The method according to claim 5, wherein the strongly polar aprotic solvent is one or a mixture of two or more of N, N-dimethylformamide, N-dimethylacetamide, dimethylsulfoxide, N-methylpyrrolidone, and sulfolane.
7. The process according to claim 4 or 6, wherein the azeotropic solvent is one or a mixture of two or more of toluene, xylene and chlorobenzene.
8. The method according to claim 7, wherein the good solvent is one or a mixture of two or more of N, N-dimethylformamide, N-dimethylacetamide, dimethylsulfoxide, N-methylpyrrolidone, sulfolane and chloroform.
9. The method according to claim 4, 6 or 8, wherein the settling agent is one or more of methanol, ethanol, isopropanol, acetone and water.
10. The method of claim 9, wherein the inert gas is one of nitrogen, argon, helium; the Lewis acid is one or the mixture of more than two of boron trichloride, boron tribromide, boron trifluoride and aluminum trichloride; the low boiling point organic solvent is one or the mixture of more than two of chloroform, dichloromethane, dichloroethane and acetonitrile.
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"Preparation of Poly(ether ketone)s Derived from 2,5-Furandicarboxylic Acid via Nucleophilic Aromatic Substitution Polymerization";Yusuke Kanetaka et al;《Journal of Polymer Science,Part A:Polymer Chemistry》;20160622;第54卷(第19期);第3094-3101页 * |
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