CN105001266A - 阻燃剂三羟甲基硫化膦笼状亚磷酸酯化合物的制备方法 - Google Patents
阻燃剂三羟甲基硫化膦笼状亚磷酸酯化合物的制备方法 Download PDFInfo
- Publication number
- CN105001266A CN105001266A CN201510404613.6A CN201510404613A CN105001266A CN 105001266 A CN105001266 A CN 105001266A CN 201510404613 A CN201510404613 A CN 201510404613A CN 105001266 A CN105001266 A CN 105001266A
- Authority
- CN
- China
- Prior art keywords
- phosphine sulfide
- caged
- warming
- preparation
- trishydroxymethyl phosphine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000003063 flame retardant Substances 0.000 title claims abstract description 28
- -1 phosphite compound Chemical class 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- VGMSVGFQEIYLCS-UHFFFAOYSA-N OC(O)(O)[PH2]=S Chemical compound OC(O)(O)[PH2]=S VGMSVGFQEIYLCS-UHFFFAOYSA-N 0.000 title abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 35
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 35
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 13
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- 238000000746 purification Methods 0.000 claims abstract description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims abstract 5
- JMXMXKRNIYCNRV-UHFFFAOYSA-N bis(hydroxymethyl)phosphanylmethanol Chemical compound OCP(CO)CO JMXMXKRNIYCNRV-UHFFFAOYSA-N 0.000 claims description 45
- 238000010792 warming Methods 0.000 claims description 30
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- 238000009413 insulation Methods 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 15
- 238000003756 stirring Methods 0.000 claims description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 12
- 238000010521 absorption reaction Methods 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 238000001291 vacuum drying Methods 0.000 claims description 8
- 238000005406 washing Methods 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 241000272517 Anseriformes Species 0.000 claims description 2
- 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 7
- 229920000728 polyester Polymers 0.000 abstract description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052698 phosphorus Inorganic materials 0.000 abstract description 4
- 239000011574 phosphorus Substances 0.000 abstract description 4
- 239000003822 epoxy resin Substances 0.000 abstract description 3
- 229920000647 polyepoxide Polymers 0.000 abstract description 3
- 229920000098 polyolefin Polymers 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000005580 one pot reaction Methods 0.000 abstract 1
- 239000004814 polyurethane Substances 0.000 abstract 1
- 229920002635 polyurethane Polymers 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 18
- 239000012065 filter cake Substances 0.000 description 12
- 238000000354 decomposition reaction Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000003610 charcoal Substances 0.000 description 5
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- QCJQWJKKTGJDCM-UHFFFAOYSA-N [P].[S] Chemical compound [P].[S] QCJQWJKKTGJDCM-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229920006305 unsaturated polyester Polymers 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000019504 cigarettes Nutrition 0.000 description 1
- 238000009841 combustion method Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000005713 exacerbation Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- ZOGYOOUMDVKYLM-UHFFFAOYSA-N phosphane phosphorous acid Chemical compound P.OP(O)O ZOGYOOUMDVKYLM-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000002341 toxic gas Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Landscapes
- Fireproofing Substances (AREA)
Abstract
Description
添加量% | LOI% | 滴落情况 | 成炭性 |
0 | 21 | 快滴落 | 不成炭 |
10 | 25 | 缓滴落 | 不成炭 |
20 | 31 | 不滴落 | 成炭 |
30 | 36 | 不滴落 | 成炭 |
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510404613.6A CN105001266B (zh) | 2015-07-07 | 2015-07-07 | 阻燃剂三羟甲基硫化膦笼状亚磷酸酯化合物的制备方法 |
Applications Claiming Priority (1)
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CN201510404613.6A CN105001266B (zh) | 2015-07-07 | 2015-07-07 | 阻燃剂三羟甲基硫化膦笼状亚磷酸酯化合物的制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN105001266A true CN105001266A (zh) | 2015-10-28 |
CN105001266B CN105001266B (zh) | 2018-02-02 |
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CN201510404613.6A Active CN105001266B (zh) | 2015-07-07 | 2015-07-07 | 阻燃剂三羟甲基硫化膦笼状亚磷酸酯化合物的制备方法 |
Country Status (1)
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3155703A (en) * | 1959-02-10 | 1964-11-03 | Rohm & Haas | Bicyclic phosphites and phosphates |
EP0666266A1 (de) * | 1994-02-08 | 1995-08-09 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von Trismethylolalkanphosphit |
CN101230274A (zh) * | 2007-12-27 | 2008-07-30 | 南京师范大学 | 环状膦酸酯或环状磷酸酯阻燃剂的制备方法 |
-
2015
- 2015-07-07 CN CN201510404613.6A patent/CN105001266B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3155703A (en) * | 1959-02-10 | 1964-11-03 | Rohm & Haas | Bicyclic phosphites and phosphates |
EP0666266A1 (de) * | 1994-02-08 | 1995-08-09 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von Trismethylolalkanphosphit |
CN101230274A (zh) * | 2007-12-27 | 2008-07-30 | 南京师范大学 | 环状膦酸酯或环状磷酸酯阻燃剂的制备方法 |
Non-Patent Citations (3)
Title |
---|
D. A. ALLISON, ET AL.: ""NMR PARAMETERS AND BONDING IN METAL, CHALCONIDE, BORANE AND CARBONIUM DERIVATIVES OF POLYCYCLIC PHOSPHORUS LIGANDS"", 《PHOSPHORUS》 * |
严慧等: "环状磷酸酯阻燃剂Antiblaze的合成", 《南京师范大学学报(工程技术版)》 * |
朱春华: "乙基双环亚磷酸酯的新工艺合成", 《精细化工原料及中间体》 * |
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CN105001266B (zh) | 2018-02-02 |
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TR01 | Transfer of patent right |
Effective date of registration: 20210421 Address after: 313018 No. 188 Liangshan Road, Linghu Town, Nanxun District, Huzhou City, Zhejiang Province Patentee after: Zhejiang Rui hi tech materials Limited by Share Ltd. Address before: 215011, Su Da Science Park, Binhe Road, 1701 hi tech Zone, Jiangsu, Suzhou Patentee before: SUZHOU KINGMAN CHEMICAL TECHNOLOGY Co.,Ltd. |
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PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Preparation method of flame retardant trimethyl sulfurized phosphine cage shaped phosphite compounds Granted publication date: 20180202 Pledgee: Zhejiang Nanxun Rural Commercial Bank branch Linghu Limited by Share Ltd. Pledgor: Zhejiang Rui hi tech materials Limited by Share Ltd. Registration number: Y2024330000544 |