CN104059228B - 一种双酚a型聚硫酸(氨)酯类化合物及其合成方法 - Google Patents
一种双酚a型聚硫酸(氨)酯类化合物及其合成方法 Download PDFInfo
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- CN104059228B CN104059228B CN201310509899.5A CN201310509899A CN104059228B CN 104059228 B CN104059228 B CN 104059228B CN 201310509899 A CN201310509899 A CN 201310509899A CN 104059228 B CN104059228 B CN 104059228B
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- bisphenol
- ammonia
- sulfuric acid
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 title claims abstract description 147
- 229930185605 Bisphenol Natural products 0.000 title claims abstract description 67
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 title claims abstract description 53
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 150000002148 esters Chemical class 0.000 title claims abstract description 38
- 229910021529 ammonia Inorganic materials 0.000 title claims abstract description 27
- 150000001875 compounds Chemical class 0.000 title claims abstract description 26
- 238000010189 synthetic method Methods 0.000 title claims description 12
- 230000004224 protection Effects 0.000 claims abstract description 41
- 239000005935 Sulfuryl fluoride Substances 0.000 claims abstract description 31
- 229940106691 bisphenol a Drugs 0.000 claims abstract description 31
- 229910001882 dioxygen Inorganic materials 0.000 claims abstract description 29
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 claims abstract description 29
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- -1 dioxygen sulfuryl fluoride compounds Chemical class 0.000 claims abstract description 16
- 150000004985 diamines Chemical class 0.000 claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims abstract description 11
- 125000004665 trialkylsilyl group Chemical group 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 16
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 229940031826 phenolate Drugs 0.000 claims description 10
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 claims description 7
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 6
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 229940043279 diisopropylamine Drugs 0.000 claims description 5
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 5
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
- 150000003053 piperidines Chemical class 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 150000001265 acyl fluorides Chemical class 0.000 claims 1
- 150000003927 aminopyridines Chemical class 0.000 claims 1
- 239000003049 inorganic solvent Substances 0.000 claims 1
- 229910001867 inorganic solvent Inorganic materials 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- 229920000728 polyester Polymers 0.000 abstract description 13
- 239000002994 raw material Substances 0.000 abstract description 11
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 238000005516 engineering process Methods 0.000 abstract description 4
- 230000005662 electromechanics Effects 0.000 abstract description 3
- 230000002194 synthesizing effect Effects 0.000 abstract description 3
- 238000003912 environmental pollution Methods 0.000 abstract description 2
- 239000011261 inert gas Substances 0.000 abstract description 2
- 229920002521 macromolecule Polymers 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract 1
- 238000004377 microelectronic Methods 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 description 43
- 229920000642 polymer Polymers 0.000 description 28
- DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000000463 material Substances 0.000 description 14
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- 238000002329 infrared spectrum Methods 0.000 description 9
- 229910052710 silicon Inorganic materials 0.000 description 9
- 239000010703 silicon Substances 0.000 description 9
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 9
- 229940095054 ammoniac Drugs 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000003513 alkali Substances 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- DOJJVTGTRZSDLJ-UHFFFAOYSA-N bisphenol A sulfate Chemical compound C=1C=C(OS(O)(=O)=O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 DOJJVTGTRZSDLJ-UHFFFAOYSA-N 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 238000013019 agitation Methods 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000004417 polycarbonate Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 230000018109 developmental process Effects 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000012973 diazabicyclooctane Substances 0.000 description 3
- 229920006351 engineering plastic Polymers 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229920000402 bisphenol A polycarbonate polymer Polymers 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000276498 Pollachius virens Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 230000006750 UV protection Effects 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 150000004651 carbonic acid esters Chemical class 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000012567 medical material Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 230000036314 physical performance Effects 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 210000004994 reproductive system Anatomy 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
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- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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AU2016282673B2 (en) | 2015-06-22 | 2020-11-12 | The Scripps Research Institute | Polymerization of silyl- and fluoro-containing monomers |
WO2019201254A1 (zh) * | 2018-04-16 | 2019-10-24 | 白银图微新材料科技有限公司 | 硫酸(胺)酯类连接子聚合物的聚合方法 |
US11127976B2 (en) * | 2019-02-26 | 2021-09-21 | Robert Bosch Gmbh | Sulfur-based polyester electrolytes for high voltage lithium ion batteries |
CN110407722A (zh) * | 2019-07-24 | 2019-11-05 | 江苏国泰超威新材料有限公司 | 一种双氟磺酰双酚苯基酯的制备方法 |
CN112495198A (zh) * | 2019-09-12 | 2021-03-16 | 白银图微新材料科技有限公司 | 聚硫酸(氨)酯聚合物制备膜技术与应用 |
CN110922598B (zh) * | 2019-12-19 | 2022-04-19 | 乌海图微新材料科技有限公司 | 一种苯二酚衍生物型聚硫酸酯的合成方法 |
CN110922597B (zh) * | 2019-12-19 | 2022-05-06 | 乌海图微新材料科技有限公司 | 一种双酚s衍生物型聚硫酸酯的合成方法 |
CN111072966B (zh) * | 2019-12-19 | 2022-06-14 | 乌海图微新材料科技有限公司 | 一种哌嗪类聚硫酰胺树脂及其合成方法 |
CN111040165A (zh) * | 2019-12-26 | 2020-04-21 | 白银图微新材料科技有限公司 | 聚磺酸酯类聚合物及其聚合方法 |
CN111116914A (zh) * | 2019-12-26 | 2020-05-08 | 白银图微新材料科技有限公司 | 聚硫酸(氨)酯聚合物为原料制备磺化聚硫酸(氨)酯的合成方法 |
US20230330628A1 (en) * | 2021-02-01 | 2023-10-19 | Soochow University | Porous crosslinked material, preparation and application thereof |
CN114149586B (zh) * | 2021-11-01 | 2024-01-26 | 白银图微新材料科技有限公司 | 一种扩链聚硫酸酯及其制备方法 |
CN113881072B (zh) * | 2021-11-02 | 2023-09-19 | 乌海图微新材料科技有限公司 | 一种分子量可控的聚硫酸酯交联方法 |
CN114752032B (zh) * | 2022-04-01 | 2023-12-22 | 内蒙古图微新材料科技有限公司 | 聚硫酸酯的扩链方法 |
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CN1305935C (zh) * | 2005-03-17 | 2007-03-21 | 吉林大学 | 电活性聚芳醚酮(砜)系列聚合物及其制备方法 |
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