CN114409704A - Furyl flame retardant and preparation method thereof - Google Patents
Furyl flame retardant and preparation method thereof Download PDFInfo
- Publication number
- CN114409704A CN114409704A CN202210098256.5A CN202210098256A CN114409704A CN 114409704 A CN114409704 A CN 114409704A CN 202210098256 A CN202210098256 A CN 202210098256A CN 114409704 A CN114409704 A CN 114409704A
- Authority
- CN
- China
- Prior art keywords
- flame retardant
- phosphorus
- furyl
- epoxy resin
- containing compound
- 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.)
- Granted
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- 239000003063 flame retardant Substances 0.000 title claims abstract description 85
- -1 Furyl flame retardant Chemical compound 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims abstract description 52
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 claims abstract description 14
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 14
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000000463 material Substances 0.000 claims abstract description 14
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 14
- 239000011574 phosphorus Substances 0.000 claims abstract description 14
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 claims abstract description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 54
- 239000003822 epoxy resin Substances 0.000 claims description 33
- 229920000647 polyepoxide Polymers 0.000 claims description 33
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 17
- 238000005406 washing Methods 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 14
- 238000001914 filtration Methods 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 10
- 239000012043 crude product Substances 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 5
- BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 0.000 claims description 4
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 4
- UBIJTWDKTYCPMQ-UHFFFAOYSA-N hexachlorophosphazene Chemical compound ClP1(Cl)=NP(Cl)(Cl)=NP(Cl)(Cl)=N1 UBIJTWDKTYCPMQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000853 adhesive Substances 0.000 claims description 3
- 230000001070 adhesive effect Effects 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 3
- KUMNEOGIHFCNQW-UHFFFAOYSA-N diphenyl phosphite Chemical compound C=1C=CC=CC=1OP([O-])OC1=CC=CC=C1 KUMNEOGIHFCNQW-UHFFFAOYSA-N 0.000 claims description 3
- 229920001971 elastomer Polymers 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 239000005060 rubber Substances 0.000 claims description 3
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003172 aldehyde group Chemical group 0.000 claims description 2
- QPKOILOWXGLVJS-UHFFFAOYSA-N bis(2-methylpropoxy)-oxophosphanium Chemical compound CC(C)CO[P+](=O)OCC(C)C QPKOILOWXGLVJS-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 claims description 2
- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims description 2
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 claims description 2
- 239000005052 trichlorosilane Substances 0.000 claims description 2
- 239000002516 radical scavenger Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 7
- 239000002131 composite material Substances 0.000 abstract description 6
- 239000001257 hydrogen Substances 0.000 abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 6
- 125000000524 functional group Chemical group 0.000 abstract description 5
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 4
- YUWBVKYVJWNVLE-UHFFFAOYSA-N [N].[P] Chemical compound [N].[P] YUWBVKYVJWNVLE-UHFFFAOYSA-N 0.000 abstract description 4
- HIVGXUNKSAJJDN-UHFFFAOYSA-N [Si].[P] Chemical compound [Si].[P] HIVGXUNKSAJJDN-UHFFFAOYSA-N 0.000 abstract description 4
- 230000008901 benefit Effects 0.000 abstract description 4
- 150000002240 furans Chemical class 0.000 abstract description 4
- 230000002195 synergetic effect Effects 0.000 abstract description 4
- 125000003118 aryl group Chemical group 0.000 abstract description 3
- 230000003993 interaction Effects 0.000 abstract description 3
- 229920000642 polymer Polymers 0.000 abstract description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract description 2
- 229920013724 bio-based polymer Polymers 0.000 abstract description 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 229910052710 silicon Inorganic materials 0.000 abstract description 2
- 239000010703 silicon Substances 0.000 abstract description 2
- 239000011159 matrix material Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 description 14
- 238000002390 rotary evaporation Methods 0.000 description 11
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000002028 Biomass Substances 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical group C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000005055 methyl trichlorosilane Substances 0.000 description 2
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 241000609240 Ambelania acida Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910003849 O-Si Inorganic materials 0.000 description 1
- VWBYXJRDIQCSLW-UHFFFAOYSA-N O=[P](c1ccccc1)c1ccccc1 Chemical compound O=[P](c1ccccc1)c1ccccc1 VWBYXJRDIQCSLW-UHFFFAOYSA-N 0.000 description 1
- 229910003872 O—Si Inorganic materials 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000010905 bagasse Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000002541 furyl group Chemical group 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
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000005445 natural material 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
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 235000015099 wheat brans Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657172—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and one oxygen atom being part of a (thio)phosphinic acid ester: (X = O, S)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/65812—Cyclic phosphazenes [P=N-]n, n>=3
- C07F9/65815—Cyclic phosphazenes [P=N-]n, n>=3 n = 3
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/5399—Phosphorus bound to nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/544—Silicon-containing compounds containing nitrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/18—Fireproof paints including high temperature resistant paints
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- 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
- D01F1/00—General methods for the manufacture of artificial filaments or the like
- D01F1/02—Addition of substances to the spinning solution or to the melt
- D01F1/07—Addition of substances to the spinning solution or to the melt for making fire- or flame-proof filaments
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/02—Flame or fire retardant/resistant
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The invention discloses a furyl flame retardant and a preparation method thereof, belonging to the technical field of phosphorus-containing bio-based flame retardant materials. The invention takes furan compounds (5-hydroxymethyl furfural and furfuryl amine) as raw materials, and combines the furan compounds with flame retardant elements such as phosphorus, nitrogen, silicon and the like, and the prepared novel furyl flame retardant contains imino active functional groups, can form stronger interaction force with polymers, and further prepares the flame retardant bio-based polymer composite material with good compatibility. The furyl flame retardant has higher phosphorus content, or contains phosphorus-nitrogen or phosphorus-silicon flame retardant elements at the same time, can exert a synergistic flame retardant effect, has the advantage of high flame retardant efficiency, has the characteristics of large molecular weight, rich aromatic ring structure, imino active functional groups and the like, can form strong interaction such as covalent bonds or hydrogen bonds with a matrix, and has the effect of mechanical enhancement.
Description
Technical Field
The invention relates to a furyl flame retardant and a preparation method thereof, belonging to the technical field of phosphorus-containing bio-based flame retardant materials.
Background
With the progress of science and technology and the rapid development of society, polymer materials have become important components of practical materials. The polymer material is a material composed of compounds with relatively high molecular mass, mainly comprises plastics, rubber, fibers, coatings, adhesives and the like, and has the most remarkable characteristic of being mainly composed of hydrocarbon elements and generally having strong flammability and flammability. However, the field of application of polymeric materials is extensive and important, with serious consequences and losses in case of fire. Therefore, it must be modified for flame retardancy to ensure safety and reliability in use.
In recent years, a strategic arrangement of global sustainable development puts higher demands on research and development technologies of flame retardant materials, and green environment-friendly flame retardant materials are a necessary trend for development of the flame retardant field. The biomass material is a natural material with abundant reserves, and has wide sources, low price, environmental protection and lower toxicity. Therefore, the biomass renewable resources are fully utilized, so that the exploitation of fossil energy can be reduced, the environment can be protected, and the biomass renewable resources are widely concerned by the scientific research community and the industrial community. With the development of bio-based materials, the preparation of a green sustainable bio-based flame retardant from materials derived from biomass is one of the hot research directions in the field of flame retardation at present.
The bio-based furan cyclic compound is a compound containing oxygen five-membered heterocyclic ring, and has attracted attention because of having structural characteristics comparable to benzene ring. It is mainly derived from agricultural and sideline products such as bagasse, corncob, wheat bran, straw, sawdust and the like, and development and utilization of the crop byproducts not only relieve resource pressure, but also improve economic benefits. The furan compound has good reactivity, thermal stability and char formation, and has wide application prospect in the aspect of preparing flame retardants.
Disclosure of Invention
[ problem ] to
At present, research on the flame retardance of furan compounds is just started, and research on furan-based flame retardants is less.
[ solution ]
In order to solve the problems, the furan compounds (5-hydroxymethylfurfural and furfuryl amine) are used as raw materials and combined with flame-retardant elements such as phosphorus, nitrogen, silicon and the like, and the prepared novel furan-based flame retardant contains imino active functional groups, can form stronger interaction force with a polymer, and further can prepare a flame-retardant bio-based polymer composite material with good compatibility. The furyl flame retardant has higher phosphorus content, or simultaneously has phosphorus-nitrogen or phosphorus-silicon flame retardant elements, and can exert a synergistic flame retardant effect; the furyl flame retardant has higher molecular weight and rich aromatic ring structure, and is not easy to migrate and separate out.
The first object of the present invention is to provide a furan-based flame retardant having the structural formula of formula i:
wherein R is1Is at least one of the following structures:
R3is at least one of a linear, branched or cyclic alkyl group of C1 to C16;
R2is at least one of the following structures:
in one embodiment of the present invention, the synthetic route of the furan-based flame retardant is as follows:
it is a second object of the present invention to provide a method for preparing a furan-based flame retardant, comprising the steps of:
(1) dissolving 5-hydroxymethylfurfural and an acid-binding agent in an organic solvent, then dropwise adding a chlorine-containing compound, reacting for 2-12 h at 0-80 ℃, filtering after the reaction is finished, washing, separating liquid, and removing the solvent to obtain an intermediate;
(2) and adding the intermediate, furfuryl amine and a phosphorus-containing compound into a reactor, reacting for 2-24 hours at 50-100 ℃, filtering and washing a crude product after the reaction, and removing a solvent to obtain the furyl flame retardant.
In an embodiment of the present invention, the acid-binding agent in step (1) is at least one of triethylamine, pyridine, sodium hydroxide, and potassium hydroxide.
In one embodiment of the present invention, the chlorine-containing compound in step (1) is at least one of phosphorus oxychloride, cyanuric chloride, trichlorosilane containing a C1-C16 linear, branched or cyclic alkyl group, and hexachlorocyclotriphosphazene.
In one embodiment of the present invention, the organic solvent in step (1) is at least one of chloroform, dichloromethane, 1, 4-dioxane, tetrahydrofuran, acetonitrile, and N, N-dimethylformamide.
In one embodiment of the present invention, the molar ratio of the 5-hydroxymethylfurfural, the chlorine atom of the chlorine-containing compound and the acid-binding agent in step (1) is 1.0: (1.0-1.1): (1.0-1.1).
In one embodiment of the present invention, the washing in step (1) is washing the filtered filtrate with water, and the solvent removal is removing the solvent from the separated organic phase by rotary evaporation.
In one embodiment of the present invention, the dissolving in step (1) is stirring dissolving.
In one embodiment of the present invention, the phosphorus-containing compound in step (2) is at least one of 9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, diphenylphosphineoxide, diphenylphosphite, dimethylphosphite, diethylphosphite, and diisobutylphosphite.
In one embodiment of the present invention, the intermediate of step (2) has a molar ratio of aldehyde group, furfuryl amine and phosphorus-containing compound of 1.0: (1.0-1.1): (1.0-1.1).
In one embodiment of the present invention, the filtration in step (2) is to filter the reaction crude product, the washing is to wash with ethanol, and the solvent removal is to remove the solvent by rotary evaporation.
The third purpose of the invention is the application of the furyl flame retardant in the field of flame retardant materials.
In one embodiment of the invention, the application includes use in plastics, rubbers, fibers, coatings, adhesives, resins, and the like.
The fourth purpose of the invention is to provide a flame-retardant epoxy resin, the components of which comprise the furan-based flame retardant.
In one embodiment of the present invention, the preparation method of the flame retardant epoxy resin comprises the following steps:
and uniformly mixing the furyl flame retardant, the epoxy resin and the curing agent, pouring the mixture into a mold, and curing to obtain the flame-retardant epoxy resin.
In one embodiment of the present invention, the epoxy resin is a commercial bisphenol a type epoxy resin.
In one embodiment of the present invention, the curing agent is 4, 4' -diaminodiphenylmethane.
In one embodiment of the present invention, the amount of the furan-based flame retardant is 5% by mass of the epoxy resin.
In one embodiment of the present invention, the stoichiometric ratio (molar ratio) of the epoxy value of the epoxy resin to the amino active hydrogen of the curing agent is 1: 1.
in one embodiment of the invention, the curing is at 100 ℃ for 2 hours; 2 hours at 150 ℃; 180 ℃ for 2 hours.
[ advantageous effects ]
(1) The furan-based flame retardant disclosed by the invention has higher phosphorus content, or has phosphorus-nitrogen or phosphorus-silicon flame retardant elements at the same time, can simultaneously exert a synergistic flame retardant effect, and has the advantage of high flame retardant efficiency.
(2) The structure of the furyl flame retardant has the characteristics of multiple aromatic ring structures, imino active functional groups, large molecular weight and the like, can form covalent bond or hydrogen bond action with a polymer, and is not easy to migrate and separate out.
(3) The furyl flame retardant is derived from natural renewable resources, meets the requirement of sustainable development, and has good economic and ecological benefits.
Detailed Description
The following description of the preferred embodiments of the present invention is provided for the purpose of better illustrating the invention and is not intended to limit the invention thereto.
The test method comprises the following steps:
limiting Oxygen Index (LOI) test: according to the ASTM D2863-2010 standard, the flame retardant property of the flame-retardant epoxy resin composite material is tested by using an HC-2 oxygen index instrument, the size of a sample strip is 130.0mm x 6.5mm x 3.2mm, and the LOI is more than 27 percent, so that the flame-retardant epoxy resin composite material belongs to a flame-retardant material.
UL-94 vertical burning test: the flame retardant epoxy resin composite was tested for flame retardancy according to ASTM D3801 using an CZF-2 vertical flame tester, with the bar dimensions 130.0mm x 13.0mm x 3.2mm and the flame rating of V-0, V-1, V-2 or No Rating (NR).
And (3) testing tensile property: the tensile properties of the flame retardant epoxy resin composite were tested using a universal tester according to ASTM D3039-08.
Example 1
A process for preparing a furanyl flame retardant I comprising the steps of:
(1) dissolving 5-hydroxymethylfurfural and triethylamine in chloroform under stirring, then dropwise adding phosphorus oxychloride, reacting for 6 hours at 0 ℃, filtering after the reaction is finished, washing the filtrate part with deionized water, separating the liquid, and removing the solvent from the organic phase by using rotary evaporation to obtain an intermediate I; wherein the molar ratio of the 5-hydroxymethylfurfural to the triethylamine to the phosphorus oxychloride is 3.0: 3.0: 1.0;
(2) mixing the intermediate I, furfuryl amine and 9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide according to a molar ratio of 1.0: 3.0: 3.0, adding the mixture into a reactor, reacting for 12 hours at 70 ℃, filtering and washing a crude product after the reaction, removing the solvent by rotary evaporation to obtain a furyl flame retardant I,1H NMR(DMSO-d6,ppm):7.29,7.36,7.41,7.43,7.47,7.50,7.75and 8.00(24H,Ar-H),7.55(3H,O-CH＝C in furan ring),6.24,6.29,6.36and 6.39(12H,C-CH＝Cin furan ring),5.14(6H,CH2-O-P),5.0(3H, N-H),4.1(3H, N-CH-P)), structural formula (la) as follows:
the specific synthetic route is as follows:
example 2
A method for preparing a furan-based flame retardant II comprises the following steps:
(1) dissolving 5-hydroxymethylfurfural and pyridine in dichloromethane under stirring, then dropwise adding cyanuric chloride, reacting for 6 hours at 10 ℃, filtering after the reaction is finished, washing the filtrate part with deionized water, separating the liquid, and removing the solvent from the organic phase by rotary evaporation to obtain an intermediate II; wherein the molar ratio of the 5-hydroxymethylfurfural to the pyridine to the cyanuric chloride is 3.1: 3.1: 1.0;
(2) and (3) mixing the intermediate II, furfuryl amine and diphenyl phosphorus oxide according to a molar ratio of 1.0: 3.1: 3.1 adding the mixture into a reactor, reacting for 10 hours at the temperature of 80 ℃, filtering and washing a crude product after the reaction, removing the solvent by rotary evaporation to obtain a furyl flame retardant II,1H NMR(DMSO-d6,ppm):7.51and 7.77(30H,Ar-H),7.55(3H,O-CH＝C in furan ring),6.24,6.29,6.36and 6.39(12H,C-CH＝C in furan ring),5.17(6H,CH2-O),5.0(3H, N-H),4.1(3H, N-CH-P), structural formula as follows:
the specific synthetic route is as follows:
example 3
A method of preparing a furanyl flame retardant iii comprising the steps of:
(1) dissolving 5-hydroxymethylfurfural and triethylamine in tetrahydrofuran under stirring, then dropwise adding methyltrichlorosilane, reacting for 4 hours at 30 ℃, filtering after the reaction is finished, washing the filtrate part with deionized water, separating liquid, and removing the solvent from an organic phase by using rotary evaporation to obtain an intermediate III; wherein the molar ratio of the 5-hydroxymethylfurfural to the triethylamine to the methyltrichlorosilane is 3.15: 3.15: 1.0;
(2) reacting intermediate III, furfuryl amine anddimethyl phosphite according to a molar ratio of 1.0: 3.1: 3.1 adding the mixture into a reactor, reacting for 24 hours at the temperature of 60 ℃, filtering and washing a crude product after the reaction, removing the solvent by rotary evaporation to obtain the furyl flame retardant III,1H NMR(DMSO-d6,ppm):7.55(3H,O-CH＝C in furan ring),6.24,6.29,6.36and 6.39(12H,C-CH＝C in furan ring),4.9(6H,CH2-O-Si),5.0(3H,N-H),4.1(3H,N-CH-P),3.66(24H,CH3-O and CH2-N), structural formula as follows:
the specific synthetic route is as follows:
example 4
A method for preparing a furyl flame retardant IV comprises the following steps:
(1) dissolving 5-hydroxymethylfurfural and triethylamine in N, N-dimethylformamide under stirring, then dropwise adding hexachlorocyclotriphosphazene, reacting for 2 hours at 60 ℃, filtering after the reaction is finished, washing the filtrate with deionized water, separating the liquid, and removing the solvent from the organic phase by rotary evaporation to obtain an intermediate IV; wherein the molar ratio of the 5-hydroxymethylfurfural to the triethylamine to the hexachlorocyclotriphosphazene is 6.1: 6.1: 1.0;
(2) and (3) mixing the intermediate IV, furfuryl amine and diphenyl phosphite according to a molar ratio of 1.0: 6.15: 6.15 is added into a reactor to react for 8 hours at the temperature of 90 ℃, after the reaction, the crude product is filtered and washed by ethanol, and the solvent is removed by rotary evaporation to obtain the furyl flame retardant IV,1H NMR(DMSO-d6,ppm):7.21and 7.40(60H,Ar-H),7.55(6H,O-CH＝C in furan ring),6.24,6.29,6.36and 6.39(24H,C-CH＝C in furan ring),4.64(12H,CH2-O-P),5.0(6H, N-H),4.1(6H, N-CH-P), structural formula as follows:
the specific synthetic route is as follows:
comparative example 1
A process for preparing a furanyl flame retardant V comprising the following steps:
mixing 9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, furfuryl amine and furfural in a molar ratio of 1.0: 1.0: 1.0, adding the mixture into a reactor, reacting for 6 hours at 70 ℃ by using ethanol as a reaction solvent, filtering a crude product after the reaction, washing the crude product by using ethanol, removing the solvent by rotary evaporation to obtain a furyl flame retardant V,1H NMR(DMSO-d67.29,7.36,7.41,7.43,7.47,7.50,7.75and 8.00(8H, Ar-H),7.55(2H, O-CH ═ C in furan ring),6.29and 6.39(4H, C-CH ═ C in furan ring),5.0(1H, N-H),4.1(1H, N-CH-P), structural formula as follows:
the specific synthetic route is as follows:
example 5
The intermediates and the furyl flame retardants in examples 1, 2, 3, and 4, and the furyl flame retardant in comparative example 1 were used for epoxy resins, as follows:
uniformly mixing the intermediate or the furyl flame retardant with commercial bisphenol A type epoxy resin (the trade name is E-44) and a curing agent 4, 4' -diaminodiphenylmethane; then pouring the mixture into a mould for curing to obtain a flame-retardant epoxy resin cured product; wherein the using amount of the intermediate or the furan-based flame retardant is 5 percent of the mass of the epoxy resin; the stoichiometric ratio (molar ratio) of the epoxy value of the epoxy resin to the amino active hydrogen of the curing agent is 1: 1; the curing conditions were: 2 hours at 100 ℃; 2 hours at 150 ℃; 180 ℃ for 2 hours.
Comparative example 2
A method for preparing a cured bisphenol A epoxy resin comprises the following steps:
uniformly mixing commercial bisphenol A epoxy resin (brand: E-44) and curing agent 4, 4' -diaminodiphenylmethane according to the stoichiometric ratio of epoxy value to amino active hydrogen of 1:1, pouring the mixture into a mold, and curing to obtain a bisphenol A epoxy resin cured product; wherein the stoichiometric ratio (molar ratio) of the epoxy value of the epoxy resin to the amino active hydrogen of the curing agent is 1: 1; the curing conditions were: 2 hours at 100 ℃; 2 hours at 150 ℃; 180 ℃ for 2 hours.
The obtained cured flame-retardant epoxy resin is tested, and the test results are as follows:
table 1 test results of example 5and comparative example 2
As seen from table 1: the oxygen index of the epoxy resin obtained after the furan-based flame retardant obtained in the embodiments 1 to 4 is cured is more than 30.0%, and the epoxy resin can reach the V-0 level of the UL-94 vertical burning test, and has more excellent flame retardant effect compared with the epoxy resin obtained after the intermediate obtained in the embodiments 1 to 4 is cured. In contrast, the oxygen index of the cured epoxy resin of the target product obtained in the comparative example 1 is lower than 30.0%, and the UL-94 vertical burning test is V-1 grade, because the furan-based flame retardant obtained in the examples 1 to 4 has a higher phosphorus content in the molecular structure, or contains phosphorus-nitrogen or phosphorus-silicon flame retardant elements at the same time, the synergistic flame retardant effect can be exerted. In comparative example 2, the cured product of bisphenol A epoxy resin E-44 currently used had an oxygen index of 24.0%, and the UL-94 vertical burning test was not rated, indicating that it was a flammable material.
It can also be seen from table 1: the epoxy resin of the cured furyl flame retardant obtained in the examples 1 to 4 has higher mechanical strength (54.2 to 56.5MPa), and the tensile strength and the elongation at break of the epoxy resin are slightly improved compared with the epoxy resin of the intermediate obtained in the corresponding examples 1 to 4 and the target product obtained in the comparative examples 1 to 2, because the furyl flame retardant obtained in the examples 1 to 4 contains a plurality of active imino functional groups in the molecular structure, can participate in the curing reaction of the epoxy resin, and further leads to the increase of the crosslinking density of the cured epoxy resin, so that the furyl flame retardant shows higher mechanical strength.
Claims (10)
1. A furyl flame retardant is characterized in that the structural formula is as shown in formula I:
wherein R is1Is at least one of the following structures:
R3is at least one of a linear, branched or cyclic alkyl group of C1 to C16;
R2is at least one of the following structures:
2. a method of preparing the furan-based flame retardant of claim 1, comprising the steps of:
(1) dissolving 5-hydroxymethylfurfural and an acid-binding agent in an organic solvent, then dropwise adding a chlorine-containing compound, reacting for 2-12 h at 0-80 ℃, filtering after the reaction is finished, washing, separating liquid, and removing the solvent to obtain an intermediate;
(2) and adding the intermediate, furfuryl amine and a phosphorus-containing compound into a reactor, reacting for 2-24 hours at 50-100 ℃, filtering and washing a crude product after the reaction, and removing a solvent to obtain the furyl flame retardant.
3. The method according to claim 2, wherein the acid scavenger in step (1) is at least one of triethylamine, pyridine, sodium hydroxide and potassium hydroxide; the chlorine-containing compound is at least one of phosphorus oxychloride, cyanuric chloride, trichlorosilane containing C1-C16 linear chain, branched chain or cyclic alkyl and hexachlorocyclotriphosphazene.
4. The method according to claim 2, wherein the phosphorus-containing compound in step (2) is at least one of 9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, diphenylphosphineoxide, diphenylphosphite, dimethylphosphite, diethylphosphite, and diisobutylphosphite.
5. The method of claim 2, wherein the molar ratio of the 5-hydroxymethylfurfural, the chlorine atoms of the chlorine-containing compound and the acid-binding agent in step (1) is 1.0: (1.0-1.1): (1.0-1.1).
6. The method according to claim 2, wherein the intermediate of step (2) has a molar ratio of aldehyde group, furfuryl amine and phosphorus-containing compound of 1.0: (1.0-1.1): (1.0-1.1).
7. Use of a furan-based flame retardant according to claim 1 in the field of flame retardant materials.
8. Use according to claim 7, characterized in that said use comprises use in plastics, rubber, fibres, coatings, adhesives, resins.
9. A flame retardant epoxy resin comprising the furan-based flame retardant of claim 1.
10. The flame retardant epoxy resin as claimed in claim 9, wherein the preparation method of the flame retardant epoxy resin comprises the following steps:
and uniformly mixing the furyl flame retardant, the epoxy resin and the curing agent, pouring the mixture into a mold, and curing to obtain the flame-retardant epoxy resin.
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