CN110643046B - 一种提高聚磷腈弹性体分子量和产率的方法 - Google Patents
一种提高聚磷腈弹性体分子量和产率的方法 Download PDFInfo
- Publication number
- CN110643046B CN110643046B CN201810582092.7A CN201810582092A CN110643046B CN 110643046 B CN110643046 B CN 110643046B CN 201810582092 A CN201810582092 A CN 201810582092A CN 110643046 B CN110643046 B CN 110643046B
- Authority
- CN
- China
- Prior art keywords
- pdcp
- reaction
- solvent
- substitution
- yield
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 238000000034 method Methods 0.000 title claims abstract description 30
- 229920003221 poly(phosphazene) elastomer Polymers 0.000 title claims abstract description 25
- 238000006243 chemical reaction Methods 0.000 claims abstract description 67
- 239000000243 solution Substances 0.000 claims abstract description 55
- 239000002904 solvent Substances 0.000 claims abstract description 44
- 238000006467 substitution reaction Methods 0.000 claims abstract description 44
- 229920000642 polymer Polymers 0.000 claims abstract description 25
- 239000002994 raw material Substances 0.000 claims abstract description 19
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- 239000000178 monomer Substances 0.000 claims abstract description 17
- 238000009835 boiling Methods 0.000 claims abstract description 15
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 14
- UBIJTWDKTYCPMQ-UHFFFAOYSA-N hexachlorophosphazene Chemical compound ClP1(Cl)=NP(Cl)(Cl)=NP(Cl)(Cl)=N1 UBIJTWDKTYCPMQ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003960 organic solvent Substances 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 10
- 239000012190 activator Substances 0.000 claims abstract description 9
- 239000011230 binding agent Substances 0.000 claims abstract description 9
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- 238000003756 stirring Methods 0.000 claims abstract description 8
- 239000003999 initiator Substances 0.000 claims abstract description 7
- 239000012716 precipitator Substances 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims abstract description 5
- 239000011259 mixed solution Substances 0.000 claims abstract description 3
- 229920002632 poly(dichlorophosphazene) polymer Polymers 0.000 claims description 74
- 238000006116 polymerization reaction Methods 0.000 claims description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 20
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 18
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 239000013543 active substance Substances 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 239000008096 xylene Substances 0.000 claims description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 230000001376 precipitating effect Effects 0.000 claims description 5
- 239000012312 sodium hydride Substances 0.000 claims description 5
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 4
- 239000003208 petroleum Substances 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
- 238000001556 precipitation Methods 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 claims description 3
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 claims description 3
- 239000005662 Paraffin oil Substances 0.000 claims description 3
- 230000003213 activating effect Effects 0.000 claims description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 229920002545 silicone oil Polymers 0.000 claims description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 3
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 claims description 2
- 229910015900 BF3 Inorganic materials 0.000 claims description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 2
- 238000012662 bulk polymerization Methods 0.000 claims description 2
- PASHVRUKOFIRIK-UHFFFAOYSA-L calcium sulfate dihydrate Chemical compound O.O.[Ca+2].[O-]S([O-])(=O)=O PASHVRUKOFIRIK-UHFFFAOYSA-L 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 claims description 2
- 125000004122 cyclic group Chemical class 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 230000001939 inductive effect Effects 0.000 claims description 2
- SURQXAFEQWPFPV-UHFFFAOYSA-L iron(2+) sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Fe+2].[O-]S([O-])(=O)=O SURQXAFEQWPFPV-UHFFFAOYSA-L 0.000 claims description 2
- WRUGWIBCXHJTDG-UHFFFAOYSA-L magnesium sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Mg+2].[O-]S([O-])(=O)=O WRUGWIBCXHJTDG-UHFFFAOYSA-L 0.000 claims description 2
- 229940061634 magnesium sulfate heptahydrate Drugs 0.000 claims description 2
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000004064 recycling Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 14
- 239000000047 product Substances 0.000 description 23
- 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 description 20
- 239000011734 sodium Substances 0.000 description 20
- 229910052708 sodium Inorganic materials 0.000 description 20
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 14
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 8
- 229920002627 poly(phosphazenes) Polymers 0.000 description 8
- 238000010992 reflux Methods 0.000 description 7
- 239000012266 salt solution Substances 0.000 description 7
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 238000001308 synthesis method Methods 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 5
- -1 methoxy, ethoxy, propoxy, butoxy Chemical group 0.000 description 5
- 238000007789 sealing Methods 0.000 description 5
- 230000002194 synthesizing effect Effects 0.000 description 5
- 238000013329 compounding Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000012643 polycondensation polymerization Methods 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- DZKXDEWNLDOXQH-UHFFFAOYSA-N 1,3,5,2,4,6-triazatriphosphinine Chemical compound N1=PN=PN=P1 DZKXDEWNLDOXQH-UHFFFAOYSA-N 0.000 description 1
- 229910015844 BCl3 Inorganic materials 0.000 description 1
- DLRBAQDATSXCER-UHFFFAOYSA-N C(C)C1=CC=C(C=C1)O.[Na] Chemical compound C(C)C1=CC=C(C=C1)O.[Na] DLRBAQDATSXCER-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 102000018779 Replication Protein C Human genes 0.000 description 1
- 108010027647 Replication Protein C Proteins 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
- C08G79/025—Polyphosphazenes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyethers (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Abstract
Description
Claims (7)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201810582092.7A CN110643046B (zh) | 2018-06-07 | 2018-06-07 | 一种提高聚磷腈弹性体分子量和产率的方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201810582092.7A CN110643046B (zh) | 2018-06-07 | 2018-06-07 | 一种提高聚磷腈弹性体分子量和产率的方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN110643046A CN110643046A (zh) | 2020-01-03 |
CN110643046B true CN110643046B (zh) | 2021-04-02 |
Family
ID=69008585
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201810582092.7A Active CN110643046B (zh) | 2018-06-07 | 2018-06-07 | 一种提高聚磷腈弹性体分子量和产率的方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN110643046B (zh) |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5161498A (zh) * | 1974-10-02 | 1976-05-28 | Horizons Research Inc | |
JPS62132935A (ja) * | 1985-12-04 | 1987-06-16 | Maruzen Petrochem Co Ltd | オルガノホスフアゼン重合体 |
JPH01236241A (ja) * | 1988-03-16 | 1989-09-21 | Idemitsu Petrochem Co Ltd | 硬化性ホスファゼン化合物の製造方法 |
EP0532396A1 (fr) * | 1991-09-11 | 1993-03-17 | Elf Atochem S.A. | Procédé de préparation de polydichlorophosphazènes à partir d'une composition précurseur à base d'hexachlorocyclotriphosphazène |
DE19743373A1 (de) * | 1997-09-30 | 1999-04-15 | Univ Heidelberg | ·3··2·P-Polyphosphazen |
CN102219911A (zh) * | 2011-04-28 | 2011-10-19 | 北京化工大学 | 一种可注射聚膦腈/明胶复合水凝胶及其制备方法 |
CN103242535A (zh) * | 2013-04-28 | 2013-08-14 | 四川大学 | 一种线型水溶性聚磷腈高分子粘胶共混改性阻燃剂 |
CN104628965A (zh) * | 2014-12-10 | 2015-05-20 | 高占虎 | 一种聚膦腈水凝胶制备方法 |
-
2018
- 2018-06-07 CN CN201810582092.7A patent/CN110643046B/zh active Active
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5161498A (zh) * | 1974-10-02 | 1976-05-28 | Horizons Research Inc | |
JPS62132935A (ja) * | 1985-12-04 | 1987-06-16 | Maruzen Petrochem Co Ltd | オルガノホスフアゼン重合体 |
JPH01236241A (ja) * | 1988-03-16 | 1989-09-21 | Idemitsu Petrochem Co Ltd | 硬化性ホスファゼン化合物の製造方法 |
EP0532396A1 (fr) * | 1991-09-11 | 1993-03-17 | Elf Atochem S.A. | Procédé de préparation de polydichlorophosphazènes à partir d'une composition précurseur à base d'hexachlorocyclotriphosphazène |
DE19743373A1 (de) * | 1997-09-30 | 1999-04-15 | Univ Heidelberg | ·3··2·P-Polyphosphazen |
CN102219911A (zh) * | 2011-04-28 | 2011-10-19 | 北京化工大学 | 一种可注射聚膦腈/明胶复合水凝胶及其制备方法 |
CN103242535A (zh) * | 2013-04-28 | 2013-08-14 | 四川大学 | 一种线型水溶性聚磷腈高分子粘胶共混改性阻燃剂 |
CN104628965A (zh) * | 2014-12-10 | 2015-05-20 | 高占虎 | 一种聚膦腈水凝胶制备方法 |
Also Published As
Publication number | Publication date |
---|---|
CN110643046A (zh) | 2020-01-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN102459143B (zh) | 取代的2-氟丙烯酸衍生物的制备 | |
CN101544555B (zh) | 聚醚酮、其单体以及其酚盐 | |
KR20110024847A (ko) | 지방족 폴리카보네이트의 연속 제조방법 | |
Liang et al. | Synthesis and characterization of benzoxazine-functionalized amine bridged bis (phenolate) lanthanide complexes and their application in the ring-opening polymerization of cyclic esters | |
WO2008075601A1 (ja) | ホスホニウム塩、アルキレンオキシド化合物重合触媒およびポリアルキレンオキシドの製造方法 | |
CN110643046B (zh) | 一种提高聚磷腈弹性体分子量和产率的方法 | |
US3636052A (en) | Hydroxyarylpolymethylenesulfonium zwitterions | |
CN103772214A (zh) | 制备乙胺丁醇和盐酸乙胺丁醇的方法 | |
KR20010093120A (ko) | 실일작용성 활성 양이온 중합체 | |
JP3942201B2 (ja) | フェニルポリシルセスキオキサンの製造方法 | |
CA2364343A1 (en) | Oligomeric silasesquioxanes and a process for preparing oligomeric silasesquioxanes | |
EP2519554B1 (en) | Polyarylene polymers and processes for preparing | |
CN109369956B (zh) | 一种聚氨酯泡沫复合阻燃剂及其制备方法 | |
CN106495977A (zh) | 一种利用微通道反应器制备派瑞林单体化合物的方法 | |
JP2850432B2 (ja) | 共重合体及びその製造方法 | |
CN112625160B (zh) | 一种端基功能化聚合物及利用炔铜进行Glaser偶联聚合反应的方法 | |
US9809523B2 (en) | Process for the high-yield preparation of P-(R)calix[9-20]arenes | |
Korshak et al. | Synthesis and properties of polycondensation polymers from compounds with asymmetric functional groups | |
CN110078922B (zh) | 一种利用钯催化的均相烯丙基取代反应合成聚砜的方法 | |
CN111072835B (zh) | 一种高软化点、用于提高橡胶抗湿滑性能的改性α-甲基苯乙烯树脂的合成方法 | |
Liu et al. | Knots for Molecular Strings of Beads | |
US3357931A (en) | Sulfonated polymeric phosphonitriles | |
Malanga et al. | Head‐to‐head polymers. XXIV. Synthesis of head‐to‐head polyisobutylene by Grignard coupling reaction | |
CN111777581B (zh) | 一种合成多联苯并呋喃及其衍生物的方法 | |
JPS62132935A (ja) | オルガノホスフアゼン重合体 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
TR01 | Transfer of patent right |
Effective date of registration: 20230417 Address after: 262709 Southwest corner of the intersection of Sanhao Road and Gongye Fourth Road, Tianliu Town, Shouguang City, Weifang City, Shandong Province Patentee after: Shandong YUENENG New Material Technology Co.,Ltd. Address before: 100029, No. 15 East Third Ring Road, Chaoyang District, Beijing Patentee before: BEIJING University OF CHEMICAL TECHNOLOGY |
|
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20230629 Address after: 262709 Southwest corner of the intersection of Sanhao Road and Gongye Fourth Road, Tianliu Town, Shouguang City, Weifang City, Shandong Province Patentee after: SHANDONG HANGXIANG NEW MATERIALS Co.,Ltd. Address before: 262709 Southwest corner of the intersection of Sanhao Road and Gongye Fourth Road, Tianliu Town, Shouguang City, Weifang City, Shandong Province Patentee before: Shandong YUENENG New Material Technology Co.,Ltd. |
|
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20240228 Address after: Room 401, Comprehensive Building of the Pilot Plant, South of Wenhua Street and East of Zhonghao Street, Haigang Development Zone, Leting County, Tangshan City, Hebei Province, China Patentee after: Hebei Kailuan Hangxiang New Materials Co.,Ltd. Country or region after: China Address before: 262709 Southwest corner of the intersection of Sanhao Road and Gongye Fourth Road, Tianliu Town, Shouguang City, Weifang City, Shandong Province Patentee before: SHANDONG HANGXIANG NEW MATERIALS Co.,Ltd. Country or region before: China |
|
TR01 | Transfer of patent right |