CN109206663A - A kind of novel nitrogen-containing antimony organic fire retardant and preparation method thereof - Google Patents
A kind of novel nitrogen-containing antimony organic fire retardant and preparation method thereof Download PDFInfo
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- CN109206663A CN109206663A CN201710535528.2A CN201710535528A CN109206663A CN 109206663 A CN109206663 A CN 109206663A CN 201710535528 A CN201710535528 A CN 201710535528A CN 109206663 A CN109206663 A CN 109206663A
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- China
- Prior art keywords
- fire retardant
- organic fire
- oxygen index
- vertical combustion
- antimony organic
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Links
- 239000003063 flame retardant Substances 0.000 title claims abstract description 212
- 229910052787 antimony Inorganic materials 0.000 title claims abstract description 143
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 title claims abstract description 142
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims abstract description 138
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 108
- 238000006243 chemical reaction Methods 0.000 claims abstract description 106
- -1 aryl boric acid Chemical compound 0.000 claims abstract description 73
- ZBCREHCWCKXVMB-UHFFFAOYSA-N [Cl].C1(=CC=CC=C1)[Sb]C1=CC=CC=C1 Chemical compound [Cl].C1(=CC=CC=C1)[Sb]C1=CC=CC=C1 ZBCREHCWCKXVMB-UHFFFAOYSA-N 0.000 claims abstract description 55
- 239000004327 boric acid Substances 0.000 claims abstract description 55
- 239000003446 ligand Substances 0.000 claims abstract description 55
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 55
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 239000002994 raw material Substances 0.000 claims abstract description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 252
- 239000001257 hydrogen Substances 0.000 claims description 109
- 229910052739 hydrogen Inorganic materials 0.000 claims description 109
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 104
- MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 claims description 52
- 229940078494 nickel acetate Drugs 0.000 claims description 52
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 52
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 26
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 claims description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 3
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 claims description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 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
- 125000003963 dichloro group Chemical group Cl* 0.000 claims description 2
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 claims description 2
- 229910000396 dipotassium phosphate Inorganic materials 0.000 claims description 2
- 235000019797 dipotassium phosphate Nutrition 0.000 claims description 2
- 229910000402 monopotassium phosphate Inorganic materials 0.000 claims description 2
- 235000019796 monopotassium phosphate Nutrition 0.000 claims description 2
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 claims description 2
- DBJLJFTWODWSOF-UHFFFAOYSA-L nickel(ii) fluoride Chemical compound F[Ni]F DBJLJFTWODWSOF-UHFFFAOYSA-L 0.000 claims description 2
- PDXOPNHXAAQJJO-UHFFFAOYSA-N nickel;trifluoromethanesulfonic acid Chemical compound [Ni].OS(=O)(=O)C(F)(F)F PDXOPNHXAAQJJO-UHFFFAOYSA-N 0.000 claims description 2
- QCYXGORGJYUYMT-UHFFFAOYSA-N nickel;triphenylphosphane Chemical compound [Ni].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QCYXGORGJYUYMT-UHFFFAOYSA-N 0.000 claims description 2
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 claims description 2
- 235000011056 potassium acetate Nutrition 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 235000011181 potassium carbonates Nutrition 0.000 claims description 2
- 239000004323 potassium nitrate Substances 0.000 claims description 2
- 235000010333 potassium nitrate Nutrition 0.000 claims description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- 235000017550 sodium carbonate Nutrition 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 235000015424 sodium Nutrition 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 246
- 239000001301 oxygen Substances 0.000 abstract description 246
- 229910052760 oxygen Inorganic materials 0.000 abstract description 246
- 238000002485 combustion reaction Methods 0.000 abstract description 244
- 238000012360 testing method Methods 0.000 abstract description 101
- 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 abstract description 62
- 230000000694 effects Effects 0.000 abstract description 51
- 239000000654 additive Substances 0.000 abstract description 48
- 230000000996 additive effect Effects 0.000 abstract description 48
- 229910052736 halogen Inorganic materials 0.000 abstract description 5
- 150000002367 halogens Chemical class 0.000 abstract description 5
- 231100000053 low toxicity Toxicity 0.000 abstract description 3
- 239000002861 polymer material Substances 0.000 abstract description 3
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 129
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 106
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 102
- 150000002431 hydrogen Chemical class 0.000 description 92
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 54
- 239000003822 epoxy resin Substances 0.000 description 51
- 229920000647 polyepoxide Polymers 0.000 description 51
- 239000012299 nitrogen atmosphere Substances 0.000 description 50
- 238000002474 experimental method Methods 0.000 description 48
- 238000011056 performance test Methods 0.000 description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 14
- 239000000463 material Substances 0.000 description 8
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 8
- 239000007789 gas Substances 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- 231100000614 poison Toxicity 0.000 description 3
- 230000007096 poisonous effect Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000004079 fireproofing Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000779 smoke Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- IBKBIJITWRZZBB-UHFFFAOYSA-N azanylidynestibane Chemical compound [Sb]#N IBKBIJITWRZZBB-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 235000019504 cigarettes Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 239000003546 flue gas Substances 0.000 description 1
- 239000003721 gunpowder Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 description 1
- IPLJNQFXJUCRNH-UHFFFAOYSA-L nickel(2+);dibromide Chemical compound [Ni+2].[Br-].[Br-] IPLJNQFXJUCRNH-UHFFFAOYSA-L 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000002341 toxic gas Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
- C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
-
- 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
- C07F9/90—Antimony compounds
- C07F9/92—Aromatic compounds
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/22—Halogen free composition
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Fireproofing Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The present invention is a kind of novel nitrogen-containing antimony organic fire retardant and preparation method thereof.It is characterized in that, using there are commonly solvents as reaction dissolvent, using containing bridge nitrogen atom ligand diphenyl antimony chlorine and aryl boric acid cheap and easy to get as raw material, be catalyzed and reacted using nickel (II), high yield highly selective obtains novel nitrogen-containing antimony organic fire retardant (I).Test result shows that novel nitrogen-containing antimony organic fire retardant has reached national standard in terms of limit oxygen index and vertical combustion two important flame retardant property indexs, obtains excellent flame retardant effect.The fire retardant has many advantages, such as that Halogen, low toxicity, additive amount are few and good with polymer material compatibility.
Description
[technical field]
The present invention relates to flame retardant area, a kind of novel nitrogen-containing antimony organic fire retardant and its preparation side are related in particular to
Method.
[background technique]
The high speed development of modern information technologies has pushed the development of macromolecule polymer material.Currently, polymer-based material
It is widely used to the every field of national defense construction and national economy.However, most of polymerization macromolecule materials, such as general is poly-
Ethylene, polypropylene, polystyrene etc. be all it is inflammable or flammable, macromolecule material product burning release poisonous and harmful flue gas make
At fire tragedy just rising year by year.Statistics shows that the main reason for causing casualties in a fire is not fiery, is firing
These smog and poison gas released in burning, have seriously endangered the safety of people's life and property.Therefore, it is high poly- how to improve synthesis
The anti-flammability of object and natural high polymer material and inhibition smoke of gunpowder generation have become a urgent problem.
Fire retardant is also known as fire-proofing chemical or fireproof agent, is one of the important auxiliary agent for synthesizing high molecular material, function is to make to close
There is flame retardancy, self-extinguishment and smoke elimination at material.Fire retardant mainly includes phosphorus system, nitrogen system, silicon systems, halogen system, intumescent, inorganic
Filler etc..Inorganic fire retardants is exploitation and uses an earliest based flame retardant, but it there are many defects, which exists
It can give off poisonous gas when burning, smog and corrosive substance, seriously affect environment, when followed by additive amount is big, will affect material
The mechanical performance of material.Halogenated flame retardant is one of current organic fire-retardant maximum in the world.It is fire-retardant due to halogenated flame retardant
It is high-efficient, it is widely used in electronics and building industry, principal item is styrene and its copolymer, thermoplastic engineering plastic and epoxy
Resin.However, the application of halogenated flame retardant is extremely limited, mainly due to this with the continuous reinforcement of environmental protection
Based flame retardant can release poisonous and hazardous gas.Therefore, exploitation non-halogen organic flame retardants become the emphasis of research.
Fire retardant containing antimony is also using a more extensive based flame retardant, mainly includes that inorganic antimony fire retardant and antimony organic hinder
Fire agent, wherein three two ladders of oxidation are the inorganic antimony fire retardants using comparative maturity.Antimony organic fire retardant mainly has antimony triphenyl,
Triphenyl dibrominated antimony.Sb system fire retardant is generally used in compounding with other fire retardants, to enhance its flame retardant property.Nitrogenous flame ratardant
Because its have many advantages, such as colourless, Halogen, low toxicity, low cigarette, do not generate etchant gas and uvioresistant due to be widely used in fire proofing wood
Material field.The advantages of developing nitrogenous antimony organic fire retardant, can effectively utilizing nitrogenated flame retardant and Sb system fire retardant, greatly
Improve its flame retardant property.
[summary of the invention]
The purpose of the present invention is to provide a kind of novel nitrogen-containing antimony organic fire retardants and preparation method thereof.
To achieve the above object of the invention, the present invention proposes technical solution below:
A kind of preparation method of novel nitrogen-containing antimony organic (III) fire retardant (I), which is characterized in that contain bridge nitrogen atom
The diphenyl antimony chlorine and aryl boric acid of ligand are raw material, using there are commonly solvents as solvent is prepared, with common inorganic salts
As reaction promoter, using Ni (II) complex as catalyst, 8-12h is reacted under the conditions of 100-120 DEG C and obtains novel contain
Nitrogen antimony organic fire retardant (I), yield 75%-97%.
The fire retardant is a kind of novel nitrogen-containing antimony organic fire retardant, and structure formula (I) is as follows:
Wherein, R1、R2、R3、R4、R5Group be hydrogen, methyl, methoxyl group, ethyl, tert-butyl, ethyoxyl, isopropyl, cyano,
One or more of normal-butyl, phenyl；R6、R7、R8、R9、R10、R11、R12、R13Group is hydrogen, methyl, ethyl, isopropyl, uncle
One or more of butyl；R14、R15、R16、R17、R18Group is hydrogen, methyl, methoxyl group, ethyoxyl, ethyl, tert-butyl, different
One or more of propyl, cyano, formoxyl, acetyl group, normal-butyl, phenyl, vinyl, acetenyl.
A kind of novel nitrogen-containing antimony organic fire retardant, which is characterized in that R1、R2、R3、R4、R5Group is hydrogen, methyl, first
One or more of oxygroup, ethyl, tert-butyl, ethyoxyl, isopropyl, cyano, normal-butyl, phenyl.
A kind of novel nitrogen-containing antimony organic fire retardant, which is characterized in that R6、R7、R8、R9、R10、R11、R12、R13Group is
One or more of hydrogen, methyl, ethyl, isopropyl, tert-butyl.
A kind of novel nitrogen-containing antimony organic fire retardant, which is characterized in that R14、R15、R16、R17、R18Group is hydrogen, first
Base, methoxyl group, ethyl, tert-butyl, ethyoxyl, isopropyl, cyano, formoxyl, acetyl group, normal-butyl, phenyl, vinyl, second
One or more of alkynyl.
The preparation method of a kind of novel nitrogen-containing antimony organic fire retardant, which is characterized in that contain bridge nitrogen atom ligand
Diphenyl antimony chlorine and aryl boric acid be raw material, using there are commonly solvents as preparing solvent, using common inorganic salts as
Reaction promoter, using Ni (II) complex as catalyst, high yield highly selective obtains novel nitrogen-containing antimony organic fire retardant
(I)。
A kind of preparation method of novel nitrogen-containing antimony organic fire retardant, which is characterized in that the novel nitrogen-containing antimony organic
Fire retardant preparation promotor used be potassium nitrate, potassium acetate, potassium carbonate, sodium carbonate, cesium carbonate, sodium bicarbonate, potassium hydrogen phosphate,
One of potassium dihydrogen phosphate, potassium tert-butoxide, sodium tert-butoxide, sodium acetate.
A kind of preparation method of novel nitrogen-containing antimony organic fire retardant, which is characterized in that the novel nitrogen-containing antimony organic
Fire retardant preparation catalyst used be nickel acetate, nickel chloride, nickel fluoride, nickelous bromide, trifluoromethanesulfonic acid nickel, nickel acetylacetonate and
One of dichloro two (triphenylphosphine) nickel.
A kind of preparation method of novel nitrogen-containing antimony organic fire retardant, which is characterized in that the novel nitrogen-containing antimony organic
Fire retardant prepares reaction condition are as follows: reacts 8-12h under nitrogen protection.
A kind of preparation method of novel nitrogen-containing antimony organic fire retardant, which is characterized in that the novel nitrogen-containing antimony organic
In fire retardant preparation, recrystallization solvent for use for one of methylene chloride, ethyl acetate, n-hexane, petroleum ether and ethyl alcohol or
It is several.
A kind of novel nitrogen-containing antimony organic fire retardant provided by the present invention have Halogen, low toxicity, additive amount it is few and with polymerize
The advantages that object material compatibility is good.Have during novel nitrogen-containing antimony organic fire retardant provided by the present invention and Epoxy burns
Have the advantage that apparent sex character is good, anti-dissolved drip performance is good and stability is good.
[Detailed description of the invention]
It is a kind of preparation approach of novel nitrogen-containing antimony organic fire retardant provided by the invention shown in attached drawing 1.
[specific embodiment]
The synthesis path of novel nitrogen-containing antimony organic fire retardant provided by the present invention refers to attached drawing 1.
Diphenyl antimony chlorine, aryl boric acid, Raney nickel and promotor containing bridge nitrogen atom ligand are added to reactor
In, backfill nitrogen 3 times is vacuumized, then solvent is added in reactor, reacts 8-12h.Solvent is removed under reduced pressure after completion of the reaction,
It is recrystallized to give target product.
Below with reference to specific preparating example, the present invention will be further described:
Embodiment 1
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R5、R6、
R7、R8、R9、R10、R11、R12、R13Group is hydrogen), 9mmol aryl boric acid (R14、R15、R16、R17、R18Group is hydrogen), 5mol%
Nickel acetate, the sodium carbonate of 2 equivalents vacuumize backfill nitrogen three times, 40ml toluene are added under nitrogen atmosphere, anti-at 120 DEG C
Answer 12h.Toluene is removed under reduced pressure after reaction, is recrystallized to give target product, yield 90% with ethyl acetate and n-hexane.
Nitrogenous antimony organic fire retardant obtained by above-described embodiment 1 is added in epoxy resin and carries out oxygen index (OI) test and hangs down
Direct combustion burns level estimate, is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, batten size 100mm × 6.5mm
× 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen index and
The performance test specific experiment of vertical combustion grade the result is as follows:
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 2
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R5、R6、
R7、R8、R9、R10、R11、R12、R13Group is hydrogen), 9mmol aryl boric acid (R14、R15、R17、R18Group is hydrogen, R16For methyl),
5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumize backfill nitrogen three times, 40ml toluene are added under nitrogen atmosphere, 120
10h is reacted at DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target product, yield with ethyl acetate and n-hexane
It is 92%.
Nitrogenous antimony organic fire retardant obtained by above-described embodiment 2 is added in epoxy resin and carries out oxygen index (OI) test and hangs down
Direct combustion burns level estimate, is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, batten size 100mm × 6.5mm
× 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen index and
The performance test specific experiment of vertical combustion grade the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 21.92 | 24.89 | 27.87 | 29.89 | 32.99 | 34.69 | 37.25 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 3
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R5、R6、
R7、R8、R9、R10、R11、R12、R13Group is hydrogen), 9mmol aryl boric acid (R14、R15、R17、R18Group is hydrogen, R16For ethyl),
5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumize backfill nitrogen three times, 40ml toluene are added under nitrogen atmosphere, 120
8h is reacted at DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target product with ethyl acetate and n-hexane, yield is
93%.
Nitrogenous antimony organic fire retardant obtained by above-described embodiment 3 is added in epoxy resin and carries out oxygen index (OI) test and hangs down
Direct combustion burns level estimate, is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, batten size 100mm × 6.5mm
× 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen index and
The performance test specific experiment of vertical combustion grade the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.03 | 25.23 | 27.87 | 29.91 | 32.91 | 34.74 | 36.89 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 4
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R5、R6、
R7、R8、R9、R10、R11、R12、R13Group is hydrogen), 9mmol aryl boric acid (R15、R16、R17、R18Group is hydrogen, R14For methyl),
5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumize backfill nitrogen three times, 40ml toluene are added under nitrogen atmosphere, 120
8h is reacted at DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target product with ethyl acetate and n-hexane, yield is
95%.
Nitrogenous antimony organic fire retardant obtained by above-described embodiment 4 is added in epoxy resin and carries out oxygen index (OI) test and hangs down
Direct combustion burns level estimate, is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, batten size 100mm × 6.5mm
× 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen index and
The performance test specific experiment of vertical combustion grade the result is as follows:
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 5
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R5、R6、
R7、R8、R9、R10、R11、R12、R13Group is hydrogen), 9mmol aryl boric acid (R14、R15、R17、R18Group is hydrogen, R16For tertiary fourth
Base), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml toluene is added under nitrogen atmosphere,
8h is reacted at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target product with ethyl acetate and n-hexane, produces
Rate is 94%.
Nitrogenous antimony organic fire retardant obtained by above-described embodiment 5 is added in epoxy resin and carries out oxygen index (OI) test and hangs down
Direct combustion burns level estimate, is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, batten size 100mm × 6.5mm
× 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen index and
The performance test specific experiment of vertical combustion grade the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.13 | 25.07 | 28.02 | 29.99 | 32.95 | 34.69 | 36.59 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 6
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R5、R6、
R7、R8、R9、R10、R11、R12、R13Group is hydrogen), 9mmol aryl boric acid (R14、R16、R17、R18Group is hydrogen, R16For methoxy
Base), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml toluene is added under nitrogen atmosphere,
10h is reacted at 120 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target product with ethyl acetate and n-hexane, produces
Rate is 85%.
Nitrogenous antimony organic fire retardant obtained by above-described embodiment 6 is added in epoxy resin and carries out oxygen index (OI) test and hangs down
Direct combustion burns level estimate, is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, batten size 100mm × 6.5mm
× 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen index and
The performance test specific experiment of vertical combustion grade the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 21.92 | 25.09 | 28.11 | 29.79 | 32.97 | 34.78 | 36.36 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 7
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R5、R6、
R7、R8、R9、R10、R11、R12、R13Group is hydrogen), 9mmol aryl boric acid (R15、R16、R17、R18Group is hydrogen, R14For ethyl),
5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumize backfill nitrogen three times, 40ml toluene are added under nitrogen atmosphere, 120
10h is reacted at DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target product, yield with ethyl acetate and n-hexane
It is 75%.
Nitrogenous antimony organic fire retardant obtained by above-described embodiment 7 is added in epoxy resin and carries out oxygen index (OI) test and hangs down
Direct combustion burns level estimate, is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, batten size 100mm × 6.5mm
× 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen index and
The performance test specific experiment of vertical combustion grade the result is as follows:
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 8
Diphenyl antimony chlorine (R of the 0.6mol containing bridge nitrogen atom ligand is added in 500mL reaction tube1、R2、R3、R4、R5、
R6、R7、R8、R9、R10、R11、R12、R13Group is hydrogen), 0.9mol aryl boric acid (R14、R16、R17、R18Group is hydrogen, R16It is different
Propyl), 3mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 200ml first is added under nitrogen atmosphere
Benzene reacts 8h at 120 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target with ethyl acetate and n-hexane and produces
Object, yield 97%.
Nitrogenous antimony organic fire retardant obtained by above-described embodiment 8 is added in epoxy resin and carries out oxygen index (OI) test and hangs down
Direct combustion burns level estimate, is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, batten size 100mm × 6.5mm
× 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen index and
The performance test specific experiment of vertical combustion grade the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 21.96 | 25.15 | 28.20 | 29.83 | 32.96 | 34.91 | 36.65 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 9
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R5、R6、
R7、R8、R9、R10、R11、R12、R13Group is hydrogen), 9mmol aryl boric acid (R14、R16、R17、R18Group is hydrogen, R16For acetyl
Base), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml toluene is added under nitrogen atmosphere,
10h is reacted at 120 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target product with ethyl acetate and n-hexane, produces
Rate is 78%.
Nitrogenous antimony organic fire retardant obtained by above-described embodiment 9 is added in epoxy resin and carries out oxygen index (OI) test and hangs down
Direct combustion burns level estimate, is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, batten size 100mm × 6.5mm
× 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen index and
The performance test specific experiment of vertical combustion grade the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 21.90 | 25.18 | 28.20 | 29.91 | 32.96 | 34.92 | 36.52 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 10
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R5、R6、
R7、R8、R9、R10、R11、R12、R13Group is hydrogen), 9mmol aryl boric acid (R14、R15、R17、R18Group is hydrogen, R16Be positive fourth
Base), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml toluene is added under nitrogen atmosphere,
8h is reacted at 120 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target product with methylene chloride and n-hexane, produces
Rate is 88%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 10 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 11
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R5、R6、
R7、R8、R9、R10、R11、R12、R13Group is hydrogen), 9mmol aryl boric acid (R14、R16、R17、R18Group is hydrogen, R16For ethylene
Base), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml toluene is added under nitrogen atmosphere,
8h is reacted at 120 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target product with ethyl acetate and n-hexane, produces
Rate is 77%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 11 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 21.97 | 25.53 | 28.01 | 29.88 | 33.02 | 34.81 | 36.51 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 12
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R4、R5、R6、R7、
R8、R9、R10、R11、R12、R13Group is hydrogen, R3For methyl) 9mmol aryl boric acid (R14、R16、R17、R18Group is hydrogen, R16For second
Alkynyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml toluene is added under nitrogen atmosphere,
8h is reacted at 120 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target product with ethyl acetate and n-hexane,
Yield is 80%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 12 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 21.93 | 25.02 | 27.63 | 29.87 | 33.05 | 34.77 | 36.31 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 13
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R4、R5、R6、R7、
R8、R9、R10、R11、R12、R13Group is hydrogen, R3For tert-butyl), 9mmol aryl boric acid (R14、R16、R17、R18Group is hydrogen, R16
For phenyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml first is added under nitrogen atmosphere
Benzene reacts 8h at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target with ethyl acetate and n-hexane and produces
Object, yield 85%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 13 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 21.94 | 25.12 | 27.65 | 29.78 | 33.04 | 34.73 | 36.32 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 14
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R4、R5、R6、R7、
R8、R9、R10、R11、R12、R13Group is hydrogen, R3For methoxyl group), 9mmol aryl boric acid (R14、R16、R17、R18Group is hydrogen, R16
For formoxyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml is added under nitrogen atmosphere
Toluene reacts 8h at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target with ethyl acetate and n-hexane
Product, yield 83%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 14 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.03 | 25.22 | 27.68 | 29.81 | 32.99 | 34.69 | 36.29 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 15
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R5、R6、R7、
R8、R9、R10、R11、R12、R13Group is hydrogen, R4For methyl), 9mmol aryl boric acid (R14、R16、R17、R18Group is hydrogen, R15For
Methyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml toluene is added under nitrogen atmosphere,
10h is reacted at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target product with methylene chloride and n-hexane,
Yield is 88%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 15 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406-1993 standard using oxygen index instrument, batten size 100mm × 6.5mm
× 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen index and
The performance test specific experiment of vertical combustion grade the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.05 | 25.02 | 27.66 | 29.73 | 33.07 | 34.69 | 36.32 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 16
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R5、R6、R7、
R8、R9、R10、R11、R12、R13Group is hydrogen, R4For ethyl), 9mmol aryl boric acid (R14、R16、R17、R18Group is hydrogen, R15For
Methyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml toluene is added under nitrogen atmosphere,
8h is reacted at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target product with methylene chloride and n-hexane,
Yield is 90%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 16 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.05 | 25.02 | 27.66 | 29.73 | 33.07 | 34.69 | 36.32 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 17
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R6、R7、
R8、R9、R10、R11、R12、R13Group is hydrogen, R5For ethyl), 9mmol aryl boric acid (R14、R16、R17、R18Group is hydrogen, R15For
Methoxyl group), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml first is added under nitrogen atmosphere
Benzene reacts 8h at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target with methylene chloride and n-hexane and produces
Object, yield 92%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 17 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.13 | 25.05 | 27.71 | 29.83 | 33.17 | 34.88 | 36.44 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 18
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R6、R7、
R8、R9、R10、R11、R12、R13Group is hydrogen, R5For methyl), 9mmol aryl boric acid (R14、R16、R17、R18Group is hydrogen, R15For
Isopropyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml first is added under nitrogen atmosphere
Benzene reacts 8h at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target with methylene chloride and n-hexane and produces
Object, yield 85%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 18 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.06 | 25.12 | 27.77 | 29.74 | 33.14 | 34.75 | 36.33 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 19
Add diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand in 100mL reaction tube1、R2、R3、R4、R5、R6、
R7、R8、R9、R10、R11、R12、R13Group is hydrogen), 9mmol aryl boric acid (R14、R16、R17、R18Group is hydrogen, R15Be positive fourth
Base), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml toluene is added under nitrogen atmosphere,
8h is reacted at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target product with methylene chloride and n-hexane, produces
Rate is 86%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 19 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.10 | 25.07 | 27.65 | 29.86 | 33.21 | 34.69 | 36.31 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 20
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R5、R6、
R7、R8、R9、R10、R11、R12、R13Group is hydrogen), 9mmol aryl boric acid (R14、R16、R17、R18Group is hydrogen, R15For acetyl
Base), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml toluene is added under nitrogen atmosphere,
10h is reacted at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target product with methylene chloride and n-hexane, produces
Rate is 87%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 20 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.12 | 25.08 | 27.66 | 29.68 | 33.02 | 34.71 | 36.51 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 21
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R5、R6、R7、
R8、R9、R10、R11、R12、R13Group is hydrogen, R5For methyl), 9mmol aryl boric acid (R14、R16、R17、R18Group is hydrogen, R15For
Methyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml toluene is added under nitrogen atmosphere,
10h is reacted at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target product with methylene chloride and n-hexane,
Yield is 78%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 21 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.23 | 25.18 | 27.76 | 29.78 | 33.12 | 34.81 | 36.61 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 22
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R5、R7、
R8、R9、R10、R11、R12、R13Group is hydrogen, R6For methyl), 9mmol aryl boric acid (R14、R15、R16、R18Group is hydrogen, R17For
Methyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml toluene is added under nitrogen atmosphere,
10h is reacted at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target product with ethyl acetate and n-hexane,
Yield is 83%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 22 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.22 | 25.19 | 27.78 | 29.75 | 33.13 | 34.82 | 36.68 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 23
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R5、R6、
R8、R9、R10、R11、R12、R13Group is hydrogen, R7For methyl), 9mmol aryl boric acid (R14、R15、R16、R18Group is hydrogen, R17For
Methyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml toluene is added under nitrogen atmosphere,
10h is reacted at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target product with ethyl acetate and n-hexane,
Yield is 88%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 23 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.24 | 25.21 | 27.79 | 29.77 | 33.15 | 34.83 | 36.78 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 24
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R5、R6、
R8、R9、R10、R11、R12、R13Group is hydrogen, R7For ethyl), 9mmol aryl boric acid (R14、R15、R16、R18Group is hydrogen, R17For
Methyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml toluene is added under nitrogen atmosphere,
10h is reacted at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target product with ethyl acetate and n-hexane,
Yield is 92%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 24 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.27 | 25.23 | 27.74 | 29.79 | 33.17 | 34.86 | 36.71 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 25
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R5、R6、
R8、R9、R10、R11、R12、R13Group is hydrogen, R7For isopropyl), 9mmol aryl boric acid (R14、R15、R16、R18Group is hydrogen, R17
For methyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml first is added under nitrogen atmosphere
Benzene reacts 10h at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target with ethyl acetate and n-hexane and produces
Object, yield 90%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 25 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.28 | 25.25 | 27.78 | 29.81 | 33.19 | 34.83 | 36.74 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 26
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R5、R6、
R8、R9、R10、R11、R12、R13Group is hydrogen, R7For tert-butyl), 9mmol aryl boric acid (R14、R15、R16、R18Group is hydrogen, R17
For methyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml first is added under nitrogen atmosphere
Benzene reacts 10h at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target with ethyl acetate and n-hexane and produces
Object, yield 87%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 26 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.31 | 25.15 | 27.81 | 29.83 | 33.21 | 34.85 | 36.80 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 27
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R5、R6、
R7、R9、R10、R11、R12、R13Group is hydrogen, R8For isopropyl), 9mmol aryl boric acid (R14、R15、R16、R18Group is hydrogen, R17
For methyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml first is added under nitrogen atmosphere
Benzene reacts 10h at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target with ethyl acetate and n-hexane and produces
Object, yield 84%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 27 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.11 | 25.19 | 27.84 | 29.85 | 33.11 | 34.95 | 36.83 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 28
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R5、R6、
R7、R9、R10、R11、R12、R13Group is hydrogen, R8For methyl), 9mmol aryl boric acid (R14、R15、R16、R18Group is hydrogen, R17For
Methyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml toluene is added under nitrogen atmosphere,
10h is reacted at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target product with ethyl acetate and n-hexane,
Yield is 85%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 28 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.18 | 25.13 | 27.86 | 29.75 | 33.14 | 34.97 | 36.66 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 29
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R5、R6、
R7、R9、R10、R11、R12、R13Group is hydrogen, R8For ethyl), 9mmol aryl boric acid (R14、R15、R16、R18Group is hydrogen, R17For
Methyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml toluene is added under nitrogen atmosphere,
10h is reacted at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target product with ethyl acetate and n-hexane,
Yield is 91%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 29 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.15 | 25.23 | 27.76 | 29.78 | 33.16 | 34.92 | 36.71 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 30
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R5、R6、
R7、R9、R10、R11、R12、R13Group is hydrogen, R8For ethyl), 9mmol aryl boric acid (R14、R15、R17、R18Group is hydrogen, R16For
Tert-butyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml first is added under nitrogen atmosphere
Benzene reacts 10h at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target with ethyl acetate and n-hexane and produces
Object, yield 86%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 30 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.17 | 25.25 | 27.66 | 29.88 | 33.18 | 34.72 | 36.61 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 31
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R5、R6、
R7、R9、R10、R11、R12、R13Group is hydrogen, R8For isopropyl), 9mmol aryl boric acid (R14、R15、R17、R18Group is hydrogen, R16
For tert-butyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml is added under nitrogen atmosphere
Toluene reacts 10h at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target with ethyl acetate and n-hexane
Product, yield 91%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 31 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.19 | 25.35 | 27.76 | 29.78 | 33.28 | 34.82 | 36.32 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 32
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R5、R6、
R7、R9、R10、R11、R12、R13Group is hydrogen, R8For methyl), 9mmol aryl boric acid (R14、R15、R17、R18Group is hydrogen, R16For
Tert-butyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml first is added under nitrogen atmosphere
Benzene reacts 10h at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target with ethyl acetate and n-hexane and produces
Object, yield 93%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 32 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.23 | 25.38 | 27.79 | 29.75 | 33.24 | 34.86 | 36.52 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 33
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R5、R6、
R8、R9、R10、R11、R12、R13Group is hydrogen, R7For methyl), 9mmol aryl boric acid (R14、R15、R17、R18Group is hydrogen, R16For
Tert-butyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml first is added under nitrogen atmosphere
Benzene reacts 10h at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target with ethyl acetate and n-hexane and produces
Object, yield 88%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 33 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 34
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R5、R6、
R8、R9、R10、R11、R12、R13Group is hydrogen, R7For ethyl), 9mmol aryl boric acid (R14、R15、R17、R18Group is hydrogen, R16For
Tert-butyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml first is added under nitrogen atmosphere
Benzene reacts 10h at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target with ethyl acetate and n-hexane and produces
Object, yield 86%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 34 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.35 | 25.49 | 27.68 | 29.79 | 33.35 | 34.78 | 36.33 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 35
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R5、R7、
R8、R9、R10、R11、R12、R13Group is hydrogen, R6For ethyl), 9mmol aryl boric acid (R14、R15、R17、R18Group is hydrogen, R16For
Tert-butyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml first is added under nitrogen atmosphere
Benzene reacts 10h at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target with ethyl acetate and n-hexane and produces
Object, yield 86%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 35 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.45 | 25.69 | 27.78 | 29.99 | 33.75 | 34.88 | 37.03 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 36
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R5、R7、
R8、R9、R10、R11、R12、R13Group is hydrogen, R6For methyl), 9mmol aryl boric acid (R14、R15、R17、R18Group is hydrogen, R16For
Tert-butyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml first is added under nitrogen atmosphere
Benzene reacts 10h at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target with ethyl acetate and n-hexane and produces
Object, yield 84%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 36 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.41 | 25.62 | 27.74 | 29.92 | 33.76 | 34.81 | 37.01 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 37
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R5、R7、
R8、R9、R10、R11、R12、R13Group is hydrogen, R6For isopropyl), 9mmol aryl boric acid (R14、R15、R17、R18Group is hydrogen, R16
For tert-butyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml is added under nitrogen atmosphere
Toluene reacts 10h at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target with ethyl acetate and n-hexane
Product, yield 88%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 37 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.43 | 25.52 | 27.71 | 29.93 | 33.56 | 34.81 | 37.07 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 38
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R4、R5、R7、
R8、R9、R10、R11、R12、R13Group is hydrogen, R6For isopropyl), 9mmol aryl boric acid (R14、R15、R17、R18Group is hydrogen, R16
For tert-butyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml is added under nitrogen atmosphere
Toluene reacts 10h at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target with ethyl acetate and n-hexane
Product, yield 85%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 38 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.45 | 25.72 | 27.81 | 29.96 | 33.59 | 34.85 | 37.17 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 39
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R4、R5、R6、R7、
R8、R9、R10、R11、R12、R13Group is hydrogen, R3For methyl), 9mmol aryl boric acid (R14、R15、R17、R18Group is hydrogen, R16For
Tert-butyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml first is added under nitrogen atmosphere
Benzene reacts 10h at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target with ethyl acetate and n-hexane and produces
Object, yield 88%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 39 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.47 | 25.52 | 27.84 | 29.97 | 33.19 | 34.75 | 36.97 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 40
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R4、R5、R6、R7、
R8、R9、R10、R11、R12、R13Group is hydrogen, R3For ethyl), 9mmol aryl boric acid (R14、R15、R17、R18Group is hydrogen, R16For
Tert-butyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml first is added under nitrogen atmosphere
Benzene reacts 10h at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target with ethyl acetate and n-hexane and produces
Object, yield 93%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 40 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.41 | 25.57 | 27.94 | 29.98 | 33.29 | 34.79 | 36.98 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 41
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R4、R5、R6、R7、
R8、R9、R10、R11、R12、R13Group is hydrogen, R3For methoxyl group), 9mmol aryl boric acid (R14、R15、R17、R18Group is hydrogen, R16
For tert-butyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml is added under nitrogen atmosphere
Toluene reacts 10h at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target with ethyl acetate and n-hexane
Product, yield 90%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 41 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.31 | 25.58 | 27.97 | 30.08 | 33.39 | 34.89 | 36.99 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 42
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R4、R5、R6、R7、
R8、R9、R10、R11、R12、R13Group is hydrogen, R3For methoxyl group), 9mmol aryl boric acid (R14、R15、R17、R18Group is hydrogen, R16
For methyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml first is added under nitrogen atmosphere
Benzene reacts 10h at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target with ethyl acetate and n-hexane and produces
Object, yield 90%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 42 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.39 | 25.68 | 27.99 | 30.28 | 33.49 | 34.99 | 37.29 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 43
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R4、R5、R6、R7、
R8、R9、R10、R11、R12、R13Group is hydrogen, R3For methoxyl group), 9mmol aryl boric acid (R14、R15、R17、R18Group is hydrogen, R16
For acetyl group), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml is added under nitrogen atmosphere
Toluene reacts 10h at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target with ethyl acetate and n-hexane
Product, yield 78%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 43 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.49 | 25.67 | 27.96 | 30.29 | 33.46 | 34.91 | 37.20 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 44
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R4、R5、R6、R7、
R8、R9、R10、R11、R12、R13Group is hydrogen, R3For methoxyl group), 9mmol aryl boric acid (R14、R15、R17、R18Group is hydrogen, R16
For normal-butyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml is added under nitrogen atmosphere
Toluene reacts 10h at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target with ethyl acetate and n-hexane
Product, yield 84%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 44 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.59 | 25.77 | 27.99 | 30.39 | 33.56 | 34.98 | 37.22 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 45
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R4、R5、R6、R7、
R8、R9、R10、R11、R12、R13Group is hydrogen, R3For methoxyl group), 9mmol aryl boric acid (R14、R15、R17、R18Group is hydrogen, R16
For isopropyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml is added under nitrogen atmosphere
Toluene reacts 10h at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target with ethyl acetate and n-hexane
Product, yield 89%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 45 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.55 | 25.72 | 27.91 | 30.37 | 33.52 | 34.93 | 37.21 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 46
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R5、R6、R7、
R8、R9、R10、R11、R12、R13Group is hydrogen, R4For methoxyl group), 9mmol aryl boric acid (R14、R15、R17、R18Group is hydrogen, R16
For isopropyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml is added under nitrogen atmosphere
Toluene reacts 10h at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target with ethyl acetate and n-hexane
Product, yield 89%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 46 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.56 | 25.74 | 27.93 | 30.39 | 33.54 | 34.96 | 37.26 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 47
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R5、R6、R7、
R8、R9、R10、R11、R12、R13Group is hydrogen, R4For ethyl), 9mmol aryl boric acid (R14、R15、R17、R18Group is hydrogen, R16For
Isopropyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml first is added under nitrogen atmosphere
Benzene reacts 10h at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target with ethyl acetate and n-hexane and produces
Object, yield 87%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 47 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.57 | 25.72 | 27.95 | 30.42 | 33.56 | 34.97 | 37.28 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 48
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R5、R6、R7、
R8、R9、R10、R11、R12、R13Group is hydrogen, R4For tert-butyl), 9mmol aryl boric acid (R14、R15、R17、R18Group is hydrogen, R16
For isopropyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml is added under nitrogen atmosphere
Toluene reacts 10h at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target with ethyl acetate and n-hexane
Product, yield 87%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 48 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.59 | 25.62 | 28.28 | 30.72 | 33.88 | 35.28 | 37.67 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 49
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R5、R6、R7、
R8、R9、R10、R11、R12、R13Group is hydrogen, R4For tert-butyl), 9mmol aryl boric acid (R14、R15、R17、R18Group is hydrogen, R16
For methyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml first is added under nitrogen atmosphere
Benzene reacts 10h at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target with ethyl acetate and n-hexane and produces
Object, yield 87%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 49 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.52 | 25.60 | 28.21 | 30.63 | 33.81 | 35.10 | 37.27 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
Embodiment 50
Diphenyl antimony chlorine (R of the 6mmol containing bridge nitrogen atom ligand is added in 100mL reaction tube1、R2、R3、R5、R6、R7、
R8、R9、R10、R11、R12、R13Group is hydrogen, R4For tert-butyl), 9mmol aryl boric acid (R14、R15、R17、R18Group is hydrogen, R16
For tert-butyl), 5mol% nickel acetate, the sodium carbonate of 2 equivalents vacuumizes backfill nitrogen three times, 40ml is added under nitrogen atmosphere
Toluene reacts 10h at 100 DEG C.Toluene is removed under reduced pressure after reaction, is recrystallized to give target with ethyl acetate and n-hexane
Product, yield 95%.
Will nitrogenous antimony organic fire retardant obtained by above-described embodiment 50 be added epoxy resin in carry out oxygen index (OI) test and
Vertical combustion level estimate is measured according to GB/T 2406.1-2008 standard using oxygen index instrument, and batten size 100mm ×
6.5mm × 3mm is measured according to UL94 standard using Vertical combustion instrument, and batten is having a size of 125mm × 13mm × 3mm.Limit oxygen refers to
Several and vertical combustion grade performance test specific experiment the result is as follows:
| Additive amount % | 0.01 | 0.05 | 0.10 | 0.15 | 0.20 | 0.25 | 0.30 |
| Oxygen index (OI) % | 22.50 | 25.23 | 28.25 | 30.33 | 33.71 | 35.13 | 37.57 |
| Combustion rating V | V-1 | V-1 | V-1 | V-0 | V-0 | V-0 | V-0 |
Test result shows novel nitrogen-containing antimony organic fire retardant in two important anti-flammabilitys of limit oxygen index and vertical combustion
National standard can be had reached in terms of index, obtain good flame retardant effect, and dosage is few, be worthy of further application.
The embodiments described above only express several embodiments of the present invention, and the description thereof is more specific and detailed, but simultaneously
Limitations on the scope of the patent of the present invention therefore cannot be interpreted as.It should be pointed out that for those of ordinary skill in the art
For, without departing from the inventive concept of the premise, various modifications and improvements can be made, these belong to guarantor of the invention
Protect range.Therefore, the scope of protection of the patent of the invention shall be subject to the appended claims.
Claims (5)
1. the present invention is a kind of novel nitrogen-containing antimony organic fire retardant and preparation method thereof, the novel nitrogen-containing antimony organic fire retardant
Structure formula (I) is as follows:
Substituent group shown in structure formula (I) is characterized in that, the R1、R2、R3、R4、R5Group is hydrogen, methyl, methoxyl group, second
One or more of base, tert-butyl, ethyoxyl, isopropyl, cyano, normal-butyl, phenyl；The R6、R7、R8、R9、R10、R11、
R12、R13Group is one or more of hydrogen, methyl, ethyl, isopropyl, tert-butyl；The R14、R15、R16、R17、R18Group
For hydrogen, methyl, methoxyl group, ethyl, tert-butyl, ethyoxyl, isopropyl, cyano, formoxyl, acetyl group, normal-butyl, phenyl, second
One or more of alkenyl, acetenyl.
2. a kind of preparation method of novel nitrogen-containing antimony organic fire retardant according to claim 1, which is characterized in that contain bridge-type
The diphenyl antimony chlorine and aryl boric acid of nitrogen atom ligand are raw material, using there are commonly solvents as solvent is prepared, with common
Inorganic salts are as reaction promoter, using Ni (II) complex as catalyst, react 8-12h under the conditions of 100-120 DEG C and obtain
Novel nitrogen-containing antimony organic fire retardant (I).
3. a kind of preparation method of novel nitrogen-containing antimony organic fire retardant according to claim 2, which is characterized in that described novel
Nitrogenous antimony organic fire retardant prepares solvent and is selected from tetrahydrofuran (THF), toluene (Toluene), acetone (Acetone), acetonitrile
(CH3CN), one of N,N-dimethylformamide (DMF).
4. a kind of preparation method of novel nitrogen-containing antimony organic fire retardant according to claim 2, which is characterized in that described novel
Nitrogenous antimony organic fire retardant preparation catalyst used is nickel acetate, nickel chloride, nickel fluoride, trifluoromethanesulfonic acid nickel, acetylacetone,2,4-pentanedione
One of nickel and dichloro two (triphenylphosphine) nickel.
5. a kind of preparation method of novel nitrogen-containing antimony organic fire retardant according to claim 2, which is characterized in that described novel
Nitrogenous antimony organic fire retardant preparation promotor used is potassium nitrate, potassium acetate, potassium carbonate, sodium carbonate, cesium carbonate, bicarbonate
One of sodium, potassium hydrogen phosphate, potassium dihydrogen phosphate, potassium tert-butoxide, sodium tert-butoxide, sodium acetate.
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| CN108410013A (en) * | 2017-11-13 | 2018-08-17 | 汝城县三鑫电化有限公司 | A kind of organic fire-retardant and preparation method thereof |
| CN113402419A (en) * | 2021-06-16 | 2021-09-17 | 湖南大学 | Method for synthesizing diarylmethane derivative |
| CN113402559A (en) * | 2021-06-15 | 2021-09-17 | 湖南大学 | Cyclic organic antimony compound and preparation method thereof |
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| CN113402419A (en) * | 2021-06-16 | 2021-09-17 | 湖南大学 | Method for synthesizing diarylmethane derivative |
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