CN101343254B - 一种含三嗪环的Gemini表面活性剂 - Google Patents
一种含三嗪环的Gemini表面活性剂 Download PDFInfo
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- CN101343254B CN101343254B CN200810055405XA CN200810055405A CN101343254B CN 101343254 B CN101343254 B CN 101343254B CN 200810055405X A CN200810055405X A CN 200810055405XA CN 200810055405 A CN200810055405 A CN 200810055405A CN 101343254 B CN101343254 B CN 101343254B
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- 239000004094 surface-active agent Substances 0.000 title claims abstract description 32
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims description 103
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 84
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 239000000243 solution Substances 0.000 claims description 28
- 238000004809 thin layer chromatography Methods 0.000 claims description 24
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 239000007864 aqueous solution Substances 0.000 claims description 17
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 14
- 238000010792 warming Methods 0.000 claims description 13
- 238000005406 washing Methods 0.000 claims description 11
- 238000010189 synthetic method Methods 0.000 claims description 10
- OTTPFCJTQXRWHO-UHFFFAOYSA-N 3-(2,3-dichloroanilino)cyclohex-2-en-1-one Chemical compound ClC1=CC=CC(NC=2CCCC(=O)C=2)=C1Cl OTTPFCJTQXRWHO-UHFFFAOYSA-N 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 abstract description 3
- 239000000693 micelle Substances 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- 239000013543 active substance Substances 0.000 description 81
- -1 alkyl bromine Chemical compound 0.000 description 30
- 238000002329 infrared spectrum Methods 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 8
- 230000002194 synthesizing effect Effects 0.000 description 8
- 239000002994 raw material Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- PXNKHKKOKWXIAQ-UHFFFAOYSA-N CCCCCCC(CC(CCS(=O)(=O)O)CC(CN)Cl)N Chemical compound CCCCCCC(CC(CCS(=O)(=O)O)CC(CN)Cl)N PXNKHKKOKWXIAQ-UHFFFAOYSA-N 0.000 description 5
- SYVACZOIOIZNGJ-UHFFFAOYSA-N CCCCCCC(CCCCCCl)N Chemical compound CCCCCCC(CCCCCCl)N SYVACZOIOIZNGJ-UHFFFAOYSA-N 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 150000002500 ions Chemical group 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000012512 characterization method Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 230000008034 disappearance Effects 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 238000002386 leaching Methods 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 125000006850 spacer group Chemical group 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- ACVJQOTXOFKLEZ-UHFFFAOYSA-N dodecane-1,6-diamine Chemical compound CCCCCCC(N)CCCCCN ACVJQOTXOFKLEZ-UHFFFAOYSA-N 0.000 description 2
- 244000144992 flock Species 0.000 description 2
- SYECJBOWSGTPLU-UHFFFAOYSA-N hexane-1,1-diamine Chemical compound CCCCCC(N)N SYECJBOWSGTPLU-UHFFFAOYSA-N 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical group C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical compound CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 description 1
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000002313 adhesive film Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 238000006065 biodegradation reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- DZVVLBSDPBGJEM-UHFFFAOYSA-N heptane;hydrate Chemical compound O.CCCCCCC DZVVLBSDPBGJEM-UHFFFAOYSA-N 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000016507 interphase Effects 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 238000003408 phase transfer catalysis Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
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CN200810055405XA CN101343254B (zh) | 2008-07-09 | 2008-07-09 | 一种含三嗪环的Gemini表面活性剂 |
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CN200810055405XA CN101343254B (zh) | 2008-07-09 | 2008-07-09 | 一种含三嗪环的Gemini表面活性剂 |
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CN101343254A CN101343254A (zh) | 2009-01-14 |
CN101343254B true CN101343254B (zh) | 2010-06-09 |
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CN200810055405XA Expired - Fee Related CN101343254B (zh) | 2008-07-09 | 2008-07-09 | 一种含三嗪环的Gemini表面活性剂 |
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Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101618300B (zh) * | 2009-08-05 | 2011-12-07 | 中北大学 | 一种三聚阴离子表面活性剂 |
CN102029125B (zh) * | 2010-10-19 | 2013-10-30 | 大连理工大学 | 双长链均三嗪类两性表面活性剂及其合成方法 |
CN102140335B (zh) * | 2011-01-17 | 2013-01-16 | 大连理工大学 | 一种含双长链均三嗪类两性表面活性剂的无碱驱油剂 |
CN102389744B (zh) * | 2011-09-09 | 2013-08-21 | 大连理工大学 | 一类均三嗪两性甜菜碱表面活性剂及其合成方法 |
CN102895912B (zh) * | 2012-10-24 | 2015-06-24 | 柳州爱格富食品科技股份有限公司 | 一种双子表面活性剂及其制备方法 |
CN103224472B (zh) * | 2013-04-07 | 2015-03-25 | 许昌学院 | 一种重金属捕集剂的制备方法 |
CN103819333A (zh) * | 2013-12-13 | 2014-05-28 | 陕西天洋投资有限公司 | 强力增油剂的制备方法 |
CN104525066B (zh) * | 2015-01-09 | 2016-06-01 | 福州大学 | 一种单分散固结胶束微粒的制备方法 |
CN105542045B (zh) * | 2016-01-15 | 2018-01-12 | 福州大学 | 一种结构固结的棒状胶束的制备方法 |
CN109971898B (zh) * | 2019-04-10 | 2021-06-22 | 温州大学 | 一种两性离子非金属鞣剂 |
CN113522158A (zh) * | 2021-07-19 | 2021-10-22 | 深圳建实科技有限公司 | 一种含松香结构的双子表面活性剂及其制备方法 |
CN116836123A (zh) * | 2023-06-21 | 2023-10-03 | 中北大学 | 一种含三嗪环阳离子Gemini表面活性剂及其应用 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5240499A (en) * | 1990-12-21 | 1993-08-31 | Hoechst Aktiengesellschaft | Surfactant triazine compounds and their use |
CN1935346A (zh) * | 2006-09-22 | 2007-03-28 | 西南石油大学 | 一种双酰胺双磺酸盐双子表面活性剂及其合成方法 |
CN101073757A (zh) * | 2007-04-02 | 2007-11-21 | 中国科学院理化技术研究所 | 一种不对称Gemini表面活性剂及其制备方法和应用 |
-
2008
- 2008-07-09 CN CN200810055405XA patent/CN101343254B/zh not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5240499A (en) * | 1990-12-21 | 1993-08-31 | Hoechst Aktiengesellschaft | Surfactant triazine compounds and their use |
CN1935346A (zh) * | 2006-09-22 | 2007-03-28 | 西南石油大学 | 一种双酰胺双磺酸盐双子表面活性剂及其合成方法 |
CN101073757A (zh) * | 2007-04-02 | 2007-11-21 | 中国科学院理化技术研究所 | 一种不对称Gemini表面活性剂及其制备方法和应用 |
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Assignee: Build bright industry (Zhuhai) Co., Ltd Assignor: Zhongbei Univ Contract record no.: 2012440000047 Denomination of invention: Gemini surfactant containing triazine ring Granted publication date: 20100609 License type: Exclusive License Open date: 20090114 Record date: 20120213 |
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