CN103570868B - (甲基)丙烯酰胺丙基三甲基氯化铵与丙烯酰胺共聚物的水溶液聚合制法 - Google Patents
(甲基)丙烯酰胺丙基三甲基氯化铵与丙烯酰胺共聚物的水溶液聚合制法 Download PDFInfo
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- CN103570868B CN103570868B CN201310516086.9A CN201310516086A CN103570868B CN 103570868 B CN103570868 B CN 103570868B CN 201310516086 A CN201310516086 A CN 201310516086A CN 103570868 B CN103570868 B CN 103570868B
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- ammonium chloride
- trimethyl ammonium
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 238000010528 free radical solution polymerization reaction Methods 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- BIVYXWUIUTXTEO-UHFFFAOYSA-N dimethyl-[1-(prop-2-enoylamino)ethyl]-propylazanium;chloride Chemical compound [Cl-].CCC[N+](C)(C)C(C)NC(=O)C=C BIVYXWUIUTXTEO-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 229920006322 acrylamide copolymer Polymers 0.000 title claims abstract description 8
- 239000000178 monomer Substances 0.000 claims abstract description 73
- 239000003999 initiator Substances 0.000 claims abstract description 40
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 30
- 125000002091 cationic group Chemical group 0.000 claims abstract description 26
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 26
- 239000002738 chelating agent Substances 0.000 claims abstract description 23
- 229910021645 metal ion Inorganic materials 0.000 claims abstract description 23
- 239000007864 aqueous solution Substances 0.000 claims abstract description 18
- 239000002131 composite material Substances 0.000 claims abstract description 3
- 239000000376 reactant Substances 0.000 claims description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- 239000003638 chemical reducing agent Substances 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 19
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 239000000084 colloidal system Substances 0.000 claims description 11
- 239000008367 deionised water Substances 0.000 claims description 11
- 229910021641 deionized water Inorganic materials 0.000 claims description 11
- 238000007599 discharging Methods 0.000 claims description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims description 9
- 235000010265 sodium sulphite Nutrition 0.000 claims description 9
- OYINQIKIQCNQOX-UHFFFAOYSA-M 2-hydroxybutyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCC(O)C[N+](C)(C)C OYINQIKIQCNQOX-UHFFFAOYSA-M 0.000 claims description 8
- SCQOZUUUCTYPPY-UHFFFAOYSA-N dimethyl-[(prop-2-enoylamino)methyl]-propylazanium;chloride Chemical compound [Cl-].CCC[N+](C)(C)CNC(=O)C=C SCQOZUUUCTYPPY-UHFFFAOYSA-N 0.000 claims description 8
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 6
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 claims description 5
- 229910001379 sodium hypophosphite Inorganic materials 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 4
- 229920002401 polyacrylamide Polymers 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 230000033116 oxidation-reduction process Effects 0.000 claims description 3
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 claims description 2
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical group [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 claims description 2
- 239000004280 Sodium formate Substances 0.000 claims description 2
- 230000032683 aging Effects 0.000 claims description 2
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 claims description 2
- 235000019254 sodium formate Nutrition 0.000 claims description 2
- 150000002505 iron Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 13
- 230000008569 process Effects 0.000 abstract description 5
- 238000005516 engineering process Methods 0.000 abstract description 4
- 230000007062 hydrolysis Effects 0.000 abstract description 4
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 125000004185 ester group Chemical group 0.000 abstract description 3
- 238000007639 printing Methods 0.000 abstract description 3
- 238000004043 dyeing Methods 0.000 abstract description 2
- 229920006317 cationic polymer Polymers 0.000 abstract 1
- 230000007613 environmental effect Effects 0.000 abstract 1
- 238000005065 mining Methods 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 description 22
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical group [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 16
- 229920001577 copolymer Polymers 0.000 description 13
- 230000005070 ripening Effects 0.000 description 13
- 239000011734 sodium Substances 0.000 description 9
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 8
- 150000001768 cations Chemical class 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- UZNHKBFIBYXPDV-UHFFFAOYSA-N trimethyl-[3-(2-methylprop-2-enoylamino)propyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)NCCC[N+](C)(C)C UZNHKBFIBYXPDV-UHFFFAOYSA-N 0.000 description 5
- -1 acryloyl-oxy Chemical group 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GQOKIYDTHHZSCJ-UHFFFAOYSA-M dimethyl-bis(prop-2-enyl)azanium;chloride Chemical compound [Cl-].C=CC[N+](C)(C)CC=C GQOKIYDTHHZSCJ-UHFFFAOYSA-M 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- IOFGECNTUNGCMK-UHFFFAOYSA-N ethyl-dimethyl-(prop-2-enoyloxymethyl)azanium Chemical compound CC[N+](C)(C)COC(=O)C=C IOFGECNTUNGCMK-UHFFFAOYSA-N 0.000 description 2
- 230000037048 polymerization activity Effects 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000011837 N,N-methylenebisacrylamide Substances 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- AJXBTRZGLDTSST-UHFFFAOYSA-N amino 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)ON AJXBTRZGLDTSST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- DJZBBNTWXXOCDV-UHFFFAOYSA-O dimethyl-[(prop-2-enoylamino)methyl]-propylazanium Chemical compound CCC[N+](C)(C)CNC(=O)C=C DJZBBNTWXXOCDV-UHFFFAOYSA-O 0.000 description 1
- BGEJUBACEWTXRM-UHFFFAOYSA-O dimethyl-[1-(prop-2-enoylamino)ethyl]-propylazanium Chemical compound CCC[N+](C)(C)C(C)NC(=O)C=C BGEJUBACEWTXRM-UHFFFAOYSA-O 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 230000003311 flocculating effect Effects 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 230000015784 hyperosmotic salinity response Effects 0.000 description 1
- 239000010842 industrial wastewater Substances 0.000 description 1
- 238000012688 inverse emulsion polymerization Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000004531 microgranule Substances 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000019394 potassium persulphate Nutrition 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- FJWZLXNYQPQPQG-UHFFFAOYSA-M sodium hydrogen peroxide hydrogen sulfite Chemical compound OO.S([O-])(O)=O.[Na+] FJWZLXNYQPQPQG-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
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- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Paper (AREA)
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CN201310516086.9A CN103570868B (zh) | 2013-10-25 | 2013-10-25 | (甲基)丙烯酰胺丙基三甲基氯化铵与丙烯酰胺共聚物的水溶液聚合制法 |
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Families Citing this family (12)
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CN104292384B (zh) * | 2014-09-19 | 2017-02-08 | 中海油天津化工研究设计院有限公司 | 一种阳离子聚丙烯酰胺反相微乳液的制备方法 |
CN104497184B (zh) * | 2014-12-15 | 2019-03-22 | 中国科学院合肥物质科学研究院 | 一种高相对分子质量丙烯酰胺丙基三甲基氯化铵类阳离子单体均聚物的制备方法 |
CN105111366A (zh) * | 2015-07-08 | 2015-12-02 | 杭州市化工研究院有限公司 | 甲基丙烯酰胺丙基三甲基氯化铵与丙烯酰胺共聚物的水溶液聚合制备方法 |
CN106349427A (zh) * | 2016-08-29 | 2017-01-25 | 浙江大川新材料股份有限公司 | 一种am与dac共聚物的制备方法 |
CN108774294B (zh) * | 2018-06-28 | 2021-02-02 | 中科乐美环保科技有限公司 | 一种三元共聚阳离子聚丙烯酰胺的制备方法 |
CN109749014B (zh) * | 2019-01-25 | 2021-04-27 | 南京理工大学 | 高特征黏度聚甲基丙烯酰胺丙基三甲基氯化铵的制备方法 |
CN109912739B (zh) * | 2019-01-25 | 2021-05-04 | 南京理工大学 | 系列化特征黏度pmaptac的制备方法 |
CN109851712B (zh) * | 2019-01-25 | 2021-04-06 | 南京理工大学 | 高相对分子质量且阳离子度系列化p(dmc-am)的制备方法 |
CN110975847A (zh) * | 2019-12-23 | 2020-04-10 | 北京林业大学 | 一种热稳定性良好的磁性阳离子水凝胶复合吸附材料 |
CN114292406B (zh) * | 2021-12-29 | 2023-10-31 | 江苏富淼科技股份有限公司 | 一种起皱粘缸剂的制备方法 |
CN114478911B (zh) * | 2022-01-26 | 2022-09-16 | 四川大学 | 两性丙烯酸聚合物复鞣剂及其制备方法 |
CN114835852A (zh) * | 2022-04-24 | 2022-08-02 | 华南农业大学 | 具有无规结构的聚丙烯酰胺季铵盐及其制备方法和应用 |
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CN101319026A (zh) * | 2008-06-18 | 2008-12-10 | 江苏飞翔化工股份有限公司 | 松香施胶剂中辅助松香分散的阳离子聚合物的制备方法 |
CN102660250A (zh) * | 2012-04-17 | 2012-09-12 | 西南石油大学 | 一种阳离子疏水缔合聚合物驱油剂及其制备方法 |
CN103319651A (zh) * | 2013-05-28 | 2013-09-25 | 山东瑞特精细化工有限公司 | 阳离子聚丙烯酰胺p(am-dac)的合成方法 |
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US20040087717A1 (en) * | 2002-11-04 | 2004-05-06 | Ge Betz, Inc. | Modified polymeric flocculants with improved performance characteristics |
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CN101319026A (zh) * | 2008-06-18 | 2008-12-10 | 江苏飞翔化工股份有限公司 | 松香施胶剂中辅助松香分散的阳离子聚合物的制备方法 |
CN102660250A (zh) * | 2012-04-17 | 2012-09-12 | 西南石油大学 | 一种阳离子疏水缔合聚合物驱油剂及其制备方法 |
CN103319651A (zh) * | 2013-05-28 | 2013-09-25 | 山东瑞特精细化工有限公司 | 阳离子聚丙烯酰胺p(am-dac)的合成方法 |
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