CN101428206A - Double-tail quaternary ammonium salt cation surface active agent and preparation method thereof - Google Patents
Double-tail quaternary ammonium salt cation surface active agent and preparation method thereof Download PDFInfo
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- CN101428206A CN101428206A CNA2008101310264A CN200810131026A CN101428206A CN 101428206 A CN101428206 A CN 101428206A CN A2008101310264 A CNA2008101310264 A CN A2008101310264A CN 200810131026 A CN200810131026 A CN 200810131026A CN 101428206 A CN101428206 A CN 101428206A
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- -1 quaternary ammonium salt cation Chemical class 0.000 title claims abstract description 9
- 239000004094 surface-active agent Substances 0.000 title abstract description 14
- 238000002360 preparation method Methods 0.000 title abstract description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 32
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 12
- 150000001350 alkyl halides Chemical class 0.000 claims abstract description 10
- 238000004821 distillation Methods 0.000 claims abstract description 10
- 239000000843 powder Substances 0.000 claims abstract description 10
- 239000007787 solid Substances 0.000 claims abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
- 238000003756 stirring Methods 0.000 claims abstract description 9
- 238000001291 vacuum drying Methods 0.000 claims abstract description 8
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000001301 oxygen Substances 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 239000003093 cationic surfactant Substances 0.000 claims description 17
- 230000006837 decompression Effects 0.000 claims description 7
- 235000015110 jellies Nutrition 0.000 claims description 7
- 239000008274 jelly Substances 0.000 claims description 7
- 238000001556 precipitation Methods 0.000 claims description 7
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 4
- 238000001914 filtration Methods 0.000 abstract description 2
- 150000002500 ions Chemical class 0.000 abstract description 2
- 238000005406 washing Methods 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 238000004458 analytical method Methods 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 238000005481 NMR spectroscopy Methods 0.000 abstract 1
- 238000010183 spectrum analysis Methods 0.000 abstract 1
- 101000637835 Homo sapiens Serum amyloid A-4 protein Proteins 0.000 description 13
- 102100032016 Serum amyloid A-4 protein Human genes 0.000 description 13
- 238000005303 weighing Methods 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 239000003899 bactericide agent Substances 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 3
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical class ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000693 micelle Substances 0.000 description 2
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 2
- NHLUVTZJQOJKCC-UHFFFAOYSA-N n,n-dimethylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCN(C)C NHLUVTZJQOJKCC-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 1
- HNTGIJLWHDPAFN-UHFFFAOYSA-N 1-bromohexadecane Chemical compound CCCCCCCCCCCCCCCCBr HNTGIJLWHDPAFN-UHFFFAOYSA-N 0.000 description 1
- YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 description 1
- CLWAXFZCVYJLLM-UHFFFAOYSA-N 1-chlorohexadecane Chemical compound CCCCCCCCCCCCCCCCCl CLWAXFZCVYJLLM-UHFFFAOYSA-N 0.000 description 1
- HOBGCONPBCCQHM-UHFFFAOYSA-N 2-(methylamino)ethane-1,1-diol Chemical compound CNCC(O)O HOBGCONPBCCQHM-UHFFFAOYSA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000012271 agricultural production Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000013335 mesoporous material Substances 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 238000005065 mining Methods 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
- 230000002794 monomerizing effect Effects 0.000 description 1
- LPUQAYUQRXPFSQ-DFWYDOINSA-M monosodium L-glutamate Chemical compound [Na+].[O-]C(=O)[C@@H](N)CCC(O)=O LPUQAYUQRXPFSQ-DFWYDOINSA-M 0.000 description 1
- 235000013923 monosodium glutamate Nutrition 0.000 description 1
- 239000004223 monosodium glutamate Substances 0.000 description 1
- BDDIUTHMWNWMRJ-UHFFFAOYSA-N octane;hydrobromide Chemical compound Br.CCCCCCCC BDDIUTHMWNWMRJ-UHFFFAOYSA-N 0.000 description 1
- 239000003129 oil well Substances 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000006916 protein interaction Effects 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a twin-tailed quaternary ammonium salt positive ion surface active agent and a preparation method thereof. The preparation method comprises the following steps sequentially: (1), adding measured acetonitrile, and dimethyl long chain alkyl tertiary amine and corresponding alkyl halide according to a certain proportion into a three neck distilling flask; (2) keeping supplying nitrogen for 10-20 minutes until oxygen is removed; and (3) continuing magnetic force stirring reaction at a temperature of 78-83 DEG C for 15-18 hours. After the reaction is complete, solvent is removed by reduced pressure distillation; pale yellow colloidal materials obtained, and acetone which is added into the materials deposit at a low temperature, and are subjected to filtration, washing by acetone twice, and vacuum drying which can produce white powdered solid. If the white powder is applied to element analysis and nuclear magnetic resonance spectral analysis, the analysis results are consistent with target products. The method has the advantages of cheap and easily attainable raw material, mild reaction condition, complete reaction, and high reaction yield, and can also be applied in common solvents such as ethyl acetate, ethanol and the like.
Description
Technical field
The present invention relates to the preparation of a kind of pair of tail quaternary ammonium salt cationic surfactant and the method for purifying and belong to class long-chain fat quaternary ammonium salt derivative and preparation method thereof.
Background technology
In recent years, (growth rate of C-SAA) is more faster than anion and nonionic in drawing together property of cationic surface agent.The polar group of C-SAA is positively charged, thus easier on electronegative surface absorption form adsorbed film and present particular performances: solid hydrophobic surfaceization, sterilization, antistatic, softness etc.These performances have not only constituted the application foundation of C-SAA in traditional application; and its application is constantly widened, in new and high technologies such as new material that development in recent years is got up, washing agent, cosmetics, food, medicine, the energy, mining, weaving, printing and dyeing, agricultural, environmental protection, water conservancy, building, microelectronics, biology, obtained to use widely.The surfactant (SAA) that have the title of " industrial monosodium glutamate " will be a kind of inexorable trend with combining of new and high technology, also be a kind of needs of SAA field development itself.
Cationic surfactant is except that the fundamental property with general surfactant, because of hydrophilic group has positive charge, has special Interfacial Adsorption performance, can be used as softening agent, bactericide, scale preventative, corrosion inhibiter, antistatic additive, emulsifying agent etc., be widely used in the oil development process, C-SAA is widely used in drilling well in oil field development, well cementation, recover the oil, collection is defeated to wait each production link, mainly is used as: shale, the mud stone inhibitor, corrosion inhibiter, AS FILTRATION LOSS CONTROLLER, bactericide, oilwell water shutoff agent, clearly, wax-proofing agent, flocculant, scale preventative, demulsifier, foaming agent, the thickened oil recovery emulsifying agent; C-SAA is mainly used in field of new: C-SAA microemulsion prepares new material, C-SAA Prepared by Sol Gel Method new material, and C-SAA template is synthesized new material, the surface modification of inorganic powder; The application of C-SAA in life science and biological technical field: since C-SAA can with protein interaction and can permeate through cell membranes, thereby be used as anti-microbial agents for a long time.C-SAA can be used to the manufacturing of various vaccines to the coagulation ability of polysaccharide, as purification meningococcin surface antigen etc.; C-SAA is being mainly reflected on the membrane separation technique on the new separation technology, because C-SAA easily is adsorbed on electronegative film surface, makes film surface-hydrophobicized, thereby influences film character and film separation process.
Traditional single head base list alkane chain surfactant is because the separation tendency that ion head elementary charge repels or aquation causes is arranged surfactant and loosened on the surface of the aqueous solution, and surface-active is not high.And the cationic surfactant of two tail single head bases because two hydrophobic tail bases are connected on the same stature base, makes that such surfactant hydrophobic effect is strong shown in Figure of description 1a, arranges closely in solution surface.Compare with corresponding conventional surfactant, two tail single head base cationic surfactants show high surface, low critical micelle concentration (cmc), low solubility and stronger good performances such as tackifying ability.They can be widely used as emulsifying agent, bactericide, dispersant, defoamer and detergent etc.
For the synthetic and purifying of this kind surfactant, current people mainly adopt following synthetic method:
1), hydramine synthetic method (Sun Baoxing, Li Li, fine chemistry industry, 1990,63-67), this method be earlier with long-chain fatty alcohol with the two long chain tertiary amine of methylamine prepared in reaction, make product with the chloromethanes quaterisation again.But this method need be used catalyst when the preparation tertiary amine, increased cost, and also need supercharging when quaterisation, has brought difficulty for technical management and industrial equipment.
2), esterquat method (Mansur S.Mohammadi, Colloids and Surfaces A:Physicochem.Eng.Aspects, 288,96-102), this method makes the tertiary amine that contains ester group with the dihydroxy ethyl methylamine with the long-chain fat acid reaction, and then with chloromethanes or the quaternized target product that obtains of dimethyl suflfate.But this method yield is not high, and reactions steps is many, is difficult for shortcomings such as purifying.
Therefore, it is few to need to seek a kind of step, and easily purifying has the synthetic route that can improve feed stock conversion, simultaneously the two tail quaternary surfactants that are synthesized is selected purified reagent efficiently, improves the efficient of purifying.
Summary of the invention
One of purpose of the present invention is to provide the method for preparation, purification and the sign of this quaternary ammonium salt cationic surfactant.This preparation method is simple to operate, and raw material is cheap and easy to get, and the reaction condition gentleness is easy to control, and equipment is not had specific (special) requirements.
Another object of the present invention is to synthesize a series of novel two tail quaternary ammonium salt cationic surfactants with this technology.This type of surfactant has high surface-active, and the performance of strong tackify and good aspects such as sterilization is particularly suitable for the emulsion polymerisation of cationic monomer and synthesizing of mesoporous material when using as emulsifying agent.In addition, can also be used for being used in tertiary oil recovery in the industrial and agricultural production and as tackifier as bactericide and anticorrisive agent.
For reaching above technical purpose, the invention provides following technical scheme.
1, a kind of quaternary ammonium salt cationic surfactant, its structural formula is as follows:
Wherein: R=C
8H
17, C
12H
25, C
16H
33, C
18H
37X=Cl, Br;
This cationic surfactant is the white powder solid, belongs to quaternary ammonium salt cationic surfactant.
2, a kind of preparation method of quaternary ammonium salt cationic surfactant, with the long-chain fat tertiary amine, its structural formula is:
R=-C wherein
8H
17,-C
12H
25,-C
16H
33,-C
18H
37Carry out quaternary ammonium reaction with alkyl halide and make, the alkyl halide skeleton symbol is: RX, wherein R=-C
8H
17,-C
12H
25,-C
16H
33,-C
18H
37, X=Cl, Br.
3, the synthetic quaternary ammonium reaction that mainly utilizes long-chain dimethyl tertiary amine and alkyl halide of this cationic surfactant.
R=-C wherein
8H
17,-C
12H
25,-C
16H
33,-C
18H
37Carry out quaternary ammonium reaction with alkyl halide and make, the alkyl halide skeleton symbol is: RX, wherein R=-C
8H
17,-C
12H
25,-C
16H
33,-C
18H
37, X=Cl, Br.
This reacts raw materials used long-chain dimethyl tertiary amine, and is homemade, and technical pure is commercially available.Alkyl halide, homemade, technical pure, commercially available.
4, the preparation method of this quaternary ammonium salt cationic surfactant may further comprise the steps successively:
(1) in three neck distillation flasks of reflux condensing tube are housed, add the acetonitrile of metering, add dimethyl long-chain alkyl tertiary amine and corresponding alkyl halide simultaneously according to a certain percentage;
(2) logical nitrogen 10-20 minute, get rid of oxygen;
(3) at 78-83 ℃ of condition lower magnetic force stirring reaction 15～18h.
5, this method reacts completely, the reaction condition gentleness.Compared with prior art, the present invention has following beneficial effect:
(1) the method raw material is cheap and easy to get, and the reaction condition gentleness is easy to operate, carries out safety, the purity height.
(2) quaternary ammonium salt cationic surfactant provided by the invention has lower surface tension.
(3) quaternary ammonium salt cationic surfactant provided by the invention has lower critical micelle concentration (cmc).
The specific embodiment
Embodiment 1
Accurately take by weighing dimethyl octylame 3.14g (0.020mol) in the triangular flask of the strap clamp cover that backflow is housed, add n-octane bromide 4.05g (0.021mol) under the room temperature, add acetonitrile 20ml, behind the feeding nitrogen 10min, at 83 ℃ of condition lower magnetic force stirring reaction 15～18h.Decompression distillation removed and desolvates after reaction finished, and obtained little yellow jelly matter, added acetone, and precipitation is filtered also and used acetone washed twice, vacuum drying to obtain white powder solid (DC more at low temperatures
8MAB).
Embodiment 2
Accurately take by weighing dimethyl lauryl amine 4.26g (0.020mol) in the triangular flask of the strap clamp cover that backflow is housed, add bromo n-dodecane 5.23g (0.021mol) under the room temperature, add acetonitrile 20ml, behind the feeding nitrogen 20min, at 83 ℃ of condition lower magnetic force stirring reaction 15～18h.Decompression distillation removed and desolvates after reaction finished, and obtained little yellow jelly matter, added acetone, and precipitation is filtered also and used acetone washed twice, vacuum drying to obtain white powder solid (DC more at low temperatures
12MAB).
Embodiment 3
Accurately take by weighing dimethyl cetylamine 5.38g (0.020mol) in the triangular flask of the strap clamp cover that backflow is housed, add bromo hexadecane 6.41g (0.021mol) under the room temperature, add acetonitrile 20ml, behind the feeding nitrogen 20min, at 78 ℃ of condition lower magnetic force stirring reaction 15～18h.Decompression distillation removed and desolvates after reaction finished, and obtained little yellow jelly matter, added acetone, and precipitation is filtered also and used acetone washed twice, vacuum drying to obtain white powder solid (DC more at low temperatures
16MAB).
Embodiment 4
Accurately take by weighing dimethyl octylame 3.14g (0.020mol) in the triangular flask of the strap clamp cover that backflow is housed, add chloro normal octane 3.12g (0.021mol) under the room temperature, add acetonitrile 20ml, behind the feeding nitrogen 15min, at 80 ℃ of condition lower magnetic force stirring reaction 15～18h.Decompression distillation removed and desolvates after reaction finished, and obtained little yellow jelly matter, added acetone, and precipitation is filtered also and used acetone washed twice, vacuum drying to obtain white powder solid (DC more at low temperatures
8MAC).
Embodiment 5
Accurately take by weighing dimethyl lauryl amine 4.26g (0.020mol) in the triangular flask of the strap clamp cover that backflow is housed, add chloro n-dodecane 4.3g (0.021mol) under the room temperature, add acetonitrile 20ml, behind the feeding nitrogen 20min, at 80 ℃ of condition lower magnetic force stirring reaction 15～18h.Decompression distillation removed and desolvates after reaction finished, and obtained little yellow jelly matter, added acetone, and precipitation is filtered also and used acetone washed twice, vacuum drying to obtain white powder solid (DC more at low temperatures
12MAC).
Embodiment 6
Accurately take by weighing dimethyl cetylamine 5.38g (0.020mol) in the triangular flask of the strap clamp cover that backflow is housed, add chloro hexadecane 5.47g (0.021mol) under the room temperature, add acetonitrile 20ml, behind the feeding nitrogen 20min, at 80 ℃ of condition lower magnetic force stirring reaction 15～18h.Decompression distillation removed and desolvates after reaction finished, and obtained little yellow jelly matter, added acetone, and precipitation is filtered also and used acetone washed twice, vacuum drying to obtain white powder solid (DC more at low temperatures
16MAC).
Claims (2)
1. quaternary ammonium salt cationic surfactant is characterized in that chemical constitution is as follows:
Wherein: R=C
8H1
7, C
12H
25, C
16H
33Or C
18H
37X=Cl, Br.
2. method for preparing the described a kind of quaternary ammonium salt cationic surfactant of claim 1, the synthetic quaternary ammonium reaction that mainly utilizes long-chain dimethyl tertiary amine and alkyl halide of this cationic surfactant,
R=C wherein
8H
17, C
12H
25, C
16H
33Or C
18H
37, it is characterized in that may further comprise the steps:
(1) in three neck distillation flasks of reflux condensing tube are housed, add the acetonitrile of metering, add dimethyl long-chain alkyl tertiary amine and corresponding alkyl halide simultaneously according to a certain percentage;
(2) logical nitrogen 10-20 minute, get rid of oxygen, prevent that amine is oxidized;
(3) at 78-83 ℃ of condition lower magnetic force stirring reaction 15～18h;
(4) decompression distillation removed and desolvates after reaction finished, and obtained little yellow jelly matter, added acetone, and precipitation is filtered also and used the acetone washed twice more at low temperatures, and vacuum drying obtains the white powder solid.
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| CN200710049744.2 | 2007-08-13 | ||
| CNA2008101310264A CN101428206A (en) | 2007-08-13 | 2008-08-12 | Double-tail quaternary ammonium salt cation surface active agent and preparation method thereof |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102351719A (en) * | 2011-10-08 | 2012-02-15 | 中国日用化学工业研究院 | Dialkyl dimethyl quaternary ammonium salt and preparation method thereof |
| CN102675130A (en) * | 2011-11-04 | 2012-09-19 | 江苏泰特尔化工有限公司 | Phase-transfer catalyst quaternary ammonium salt and preparation method thereof |
| CN103191671A (en) * | 2013-04-17 | 2013-07-10 | 重庆理工大学 | Trimeric quaternary ammonium salt type cationic surface active agent and preparation method thereof |
| CN103821011A (en) * | 2014-02-13 | 2014-05-28 | 苏州联胜化学有限公司 | Environment-friendly acrylic fiber dye leveler, preparation method and applications thereof |
| CN109456199A (en) * | 2018-11-15 | 2019-03-12 | 广东菲安妮皮具股份有限公司 | A kind of preparation method of leather high-effective cationic surfactant |
| CN112403684A (en) * | 2020-11-25 | 2021-02-26 | 河南资环检测科技有限公司 | Synthesis method and application of xanthic acid-quaternary ammonium salt ionic liquid |
| CN112457202A (en) * | 2020-12-10 | 2021-03-09 | 山东泰和水处理科技股份有限公司 | Synthesis process of dialkyl dimethyl ammonium chloride |
-
2008
- 2008-08-12 CN CNA2008101310264A patent/CN101428206A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102351719A (en) * | 2011-10-08 | 2012-02-15 | 中国日用化学工业研究院 | Dialkyl dimethyl quaternary ammonium salt and preparation method thereof |
| CN102351719B (en) * | 2011-10-08 | 2014-07-02 | 中国日用化学工业研究院 | Dialkyl dimethyl quaternary ammonium salt and preparation method thereof |
| CN102675130A (en) * | 2011-11-04 | 2012-09-19 | 江苏泰特尔化工有限公司 | Phase-transfer catalyst quaternary ammonium salt and preparation method thereof |
| CN103191671A (en) * | 2013-04-17 | 2013-07-10 | 重庆理工大学 | Trimeric quaternary ammonium salt type cationic surface active agent and preparation method thereof |
| CN103191671B (en) * | 2013-04-17 | 2015-07-08 | 重庆理工大学 | Trimeric quaternary ammonium salt type cationic surface active agent and preparation method thereof |
| CN103821011A (en) * | 2014-02-13 | 2014-05-28 | 苏州联胜化学有限公司 | Environment-friendly acrylic fiber dye leveler, preparation method and applications thereof |
| CN109456199A (en) * | 2018-11-15 | 2019-03-12 | 广东菲安妮皮具股份有限公司 | A kind of preparation method of leather high-effective cationic surfactant |
| CN112403684A (en) * | 2020-11-25 | 2021-02-26 | 河南资环检测科技有限公司 | Synthesis method and application of xanthic acid-quaternary ammonium salt ionic liquid |
| CN112457202A (en) * | 2020-12-10 | 2021-03-09 | 山东泰和水处理科技股份有限公司 | Synthesis process of dialkyl dimethyl ammonium chloride |
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Application publication date: 20090513 |