CN113736004A - 一种乙烯-乙烯醇共聚物及其制备方法和应用 - Google Patents
一种乙烯-乙烯醇共聚物及其制备方法和应用 Download PDFInfo
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- CN113736004A CN113736004A CN202111164617.3A CN202111164617A CN113736004A CN 113736004 A CN113736004 A CN 113736004A CN 202111164617 A CN202111164617 A CN 202111164617A CN 113736004 A CN113736004 A CN 113736004A
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- China
- Prior art keywords
- ethylene
- vinyl alcohol
- alcohol copolymer
- vinyl acetate
- acetate copolymer
- 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
- 229920000219 Ethylene vinyl alcohol Polymers 0.000 title claims abstract description 85
- 238000002360 preparation method Methods 0.000 title abstract description 14
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 claims abstract description 51
- 239000005038 ethylene vinyl acetate Substances 0.000 claims abstract description 50
- 238000006136 alcoholysis reaction Methods 0.000 claims abstract description 38
- 239000011831 acidic ionic liquid Substances 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 28
- 239000002904 solvent Substances 0.000 claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- 238000002156 mixing Methods 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 11
- 239000005977 Ethylene Substances 0.000 claims description 11
- 238000001914 filtration Methods 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- 238000001556 precipitation Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- QOHANVRCHGWPNG-UHFFFAOYSA-N 1-ethyl-3-methyl-2h-imidazole;sulfuric acid Chemical compound OS(O)(=O)=O.CCN1CN(C)C=C1 QOHANVRCHGWPNG-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 4
- IZZXUYYYPZPVJF-UHFFFAOYSA-N S(O)(O)(=O)=O.CN1CN(C=C1)CCCCCCCC Chemical compound S(O)(O)(=O)=O.CN1CN(C=C1)CCCCCCCC IZZXUYYYPZPVJF-UHFFFAOYSA-N 0.000 claims description 3
- FYWVMROQEMIMSK-UHFFFAOYSA-N butane-1-sulfonic acid;hydrogen sulfate;3-methyl-1h-imidazol-3-ium Chemical compound OS([O-])(=O)=O.C[N+]=1C=CNC=1.CCCCS(O)(=O)=O FYWVMROQEMIMSK-UHFFFAOYSA-N 0.000 claims description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims description 3
- 239000012567 medical material Substances 0.000 claims description 3
- 239000005022 packaging material Substances 0.000 claims description 3
- 239000004753 textile Substances 0.000 claims description 3
- 238000001291 vacuum drying Methods 0.000 claims description 3
- WEZFRVSBUPJHFG-UHFFFAOYSA-N 3-hexyl-1-methyl-1,2-dihydroimidazol-1-ium;hydrogen sulfate Chemical compound OS([O-])(=O)=O.CCCCCCN1C[NH+](C)C=C1 WEZFRVSBUPJHFG-UHFFFAOYSA-N 0.000 claims description 2
- 238000012662 bulk polymerization Methods 0.000 claims description 2
- 239000004035 construction material Substances 0.000 claims description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 2
- 239000004715 ethylene vinyl alcohol Substances 0.000 abstract description 39
- UFRKOOWSQGXVKV-UHFFFAOYSA-N ethene;ethenol Chemical compound C=C.OC=C UFRKOOWSQGXVKV-UHFFFAOYSA-N 0.000 abstract description 37
- 229910021645 metal ion Inorganic materials 0.000 abstract description 10
- 229910052751 metal Inorganic materials 0.000 abstract description 5
- 239000002184 metal Substances 0.000 abstract description 5
- 150000002500 ions Chemical group 0.000 abstract description 4
- 238000000746 purification Methods 0.000 abstract description 4
- 238000000926 separation method Methods 0.000 abstract description 4
- 230000000052 comparative effect Effects 0.000 description 22
- WXMVWUBWIHZLMQ-UHFFFAOYSA-N 3-methyl-1-octylimidazolium Chemical compound CCCCCCCCN1C=C[N+](C)=C1 WXMVWUBWIHZLMQ-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 8
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 239000002608 ionic liquid Substances 0.000 description 7
- 230000001376 precipitating effect Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- RVEJOWGVUQQIIZ-UHFFFAOYSA-N 1-hexyl-3-methylimidazolium Chemical compound CCCCCCN1C=C[N+](C)=C1 RVEJOWGVUQQIIZ-UHFFFAOYSA-N 0.000 description 5
- -1 Polyethylene Polymers 0.000 description 5
- 230000004888 barrier function Effects 0.000 description 4
- HVVRUQBMAZRKPJ-UHFFFAOYSA-N 1,3-dimethylimidazolium Chemical compound CN1C=C[N+](C)=C1 HVVRUQBMAZRKPJ-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- RZXDTJIXPSCHCI-UHFFFAOYSA-N hexa-1,5-diene-2,5-diol Chemical compound OC(=C)CCC(O)=C RZXDTJIXPSCHCI-UHFFFAOYSA-N 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 description 1
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 1
- XIYUIMLQTKODPS-UHFFFAOYSA-M 1-ethyl-3-methylimidazol-3-ium;acetate Chemical compound CC([O-])=O.CC[N+]=1C=CN(C)C=1 XIYUIMLQTKODPS-UHFFFAOYSA-M 0.000 description 1
- HZKDSQCZNUUQIF-UHFFFAOYSA-M 1-ethyl-3-methylimidazol-3-ium;hydrogen sulfate Chemical compound OS([O-])(=O)=O.CCN1C=C[N+](C)=C1 HZKDSQCZNUUQIF-UHFFFAOYSA-M 0.000 description 1
- AQCYTEFBYQAOEP-UHFFFAOYSA-M 1-hexyl-3-methylimidazol-3-ium;acetate Chemical compound CC([O-])=O.CCCCCC[N+]=1C=CN(C)C=1 AQCYTEFBYQAOEP-UHFFFAOYSA-M 0.000 description 1
- TVCNKZCRZIIOOR-UHFFFAOYSA-M 1-hexyl-3-methylimidazol-3-ium;hydrogen sulfate Chemical compound OS([O-])(=O)=O.CCCCCC[N+]=1C=CN(C)C=1 TVCNKZCRZIIOOR-UHFFFAOYSA-M 0.000 description 1
- OCKSGCYIEVTYRG-UHFFFAOYSA-M 1-methyl-3-octylimidazol-1-ium;acetate Chemical compound CC([O-])=O.CCCCCCCC[N+]=1C=CN(C)C=1 OCKSGCYIEVTYRG-UHFFFAOYSA-M 0.000 description 1
- 238000004483 ATR-FTIR spectroscopy Methods 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 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 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- RCNFOZUBFOFJKZ-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-hexyl-3-methylimidazol-3-ium Chemical compound CCCCCC[N+]=1C=CN(C)C=1.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F RCNFOZUBFOFJKZ-UHFFFAOYSA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- RRABSTHQUPQUTI-UHFFFAOYSA-M hydron;1-methyl-3-octylimidazol-1-ium;sulfate Chemical compound OS([O-])(=O)=O.CCCCCCCCN1C=C[N+](C)=C1 RRABSTHQUPQUTI-UHFFFAOYSA-M 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/12—Hydrolysis
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
Claims (10)
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114160107A (zh) * | 2021-12-15 | 2022-03-11 | 中国人民解放军96901部队23分队 | 肼类废水吸附剂及其制备方法 |
CN115433301A (zh) * | 2022-10-12 | 2022-12-06 | 中国科学院大连化学物理研究所 | 一种乙烯-乙烯醇共聚物及其制备方法和应用 |
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2021
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JPH0559116A (ja) * | 1991-01-18 | 1993-03-09 | Kuraray Co Ltd | エチレン−ビニルアルコール共重合体の製造方法 |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114160107A (zh) * | 2021-12-15 | 2022-03-11 | 中国人民解放军96901部队23分队 | 肼类废水吸附剂及其制备方法 |
CN115433301A (zh) * | 2022-10-12 | 2022-12-06 | 中国科学院大连化学物理研究所 | 一种乙烯-乙烯醇共聚物及其制备方法和应用 |
CN115433301B (zh) * | 2022-10-12 | 2024-02-02 | 中国科学院大连化学物理研究所 | 一种乙烯-乙烯醇共聚物及其制备方法和应用 |
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