CN103145568A - Cardanol cationoid quaternary ammonium salt and preparation method thereof - Google Patents
Cardanol cationoid quaternary ammonium salt and preparation method thereof Download PDFInfo
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- CN103145568A CN103145568A CN2013100848088A CN201310084808A CN103145568A CN 103145568 A CN103145568 A CN 103145568A CN 2013100848088 A CN2013100848088 A CN 2013100848088A CN 201310084808 A CN201310084808 A CN 201310084808A CN 103145568 A CN103145568 A CN 103145568A
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Abstract
The present invention relates to a kind of Cardanol cationoid quaternary ammonium salts and preparation method thereof of lower formula (I). R1, R2, R3 are respectively identical or different in formula (I), independently selected from methyl, ethyl or propyl; X is halogen. The preparation method is that: anacardol is carried out reacting obtained anacardol intermediate first with formaldehyde, then anacardol intermediate, tertiary amine and epoxyhalopropane are reacted and are made. The Cardanol cationoid quaternary ammonium salt of the invention has excellent surface-active, and preparation is simple, raw material sources are extensive, and yield is higher.
Description
Technical field
The present invention relates to a kind of tensio-active agent and preparation method thereof, relate more specifically to a kind of cardanol quaternary ammonium salt cationic and preparation method thereof, belong to the organic chemical synthesis field.
Background technology
Cardanol (Cardanol), a kind of active single component phenol from extracted from cashew nut shell liquid, it has the activity of petroleum phenol, it is a kind of monohydroxy phenols biomass material that connects a chain alkyl on position between phenolic hydroxyl group, it has multiple good characteristic, as extensive, renewable, the low toxicity and biodegradable etc. of originating.In concrete the application, its alternative petroleum phenol is used for the industrial surface activity agent of development of new, can be applicable to the fields such as daily use chemicals, food, pharmacy, chemical industry and oil production.
Have above-mentioned good characteristic and property of many uses just because of cardanol, people have shown keen interest to its exploitation, and its chemical modification has been carried out a large amount of research, to try hard to expand its range of application.
Disclose take saturated cardanol as raw material in CN102206336 A, synthesized a series of non-ionic type polyether surfactants with following formula (a) structure: wherein, n=2-30, side chain are the straight chain saturated alkyl of 15 carbon.
The people such as Bruce (Tymal J H P, Bruce I E.
Synthesis and characterization of polyethoxylate surfactants derived from phenolic lipids. Journal of surfactants and detergents, 2003,6 (3): 294-297)Disclose take unsaturated cardanol as raw material, synthesized the nonionic surface active agent with following formula (b) structure:
N=5-30 wherein, the performance test result of study shows, when n=13-14, has very strong surfactivity and biological degradability.
Disclose saturated cardanol polyoxyethylene ether take the bibliographical information of patent CN102206336 A in CN101941926 A as raw material, with the thionamic acid reaction, synthesized the nonionic surface active agent of following formula (c) structure:
N=2-25 wherein.
The people such as Wang Jun (Wang Jun, Liu Changhuan, Li Cuiqin etc.,
Synthetic and the surface properties of cashew nut based surfactants. applied chemistry, 2011,22 (2): 48-51) take unsaturated cardanol, oxyethane and Mono Chloro Acetic Acid as raw material, synthesized the nonionic surface active agent of following formula (d) structure-cardanol polyoxyethylene ether carboxylic acid sodium by two-step reaction: by its surface-active result of study is shown, this tensio-active agent has surfactivity, foaming properties and wettability preferably.
CN102728272 A discloses with saturated cardanol and formaldehyde, secondary amine and chloroparaffin reaction, has synthesized the tensio-active agent of following formula (e) structure:
By studies show that, this tensio-active agent has higher surfactivity.
CN102824876 A discloses with cardanol and epoxy compounds, reactive tertiary amine, has synthesized the cationic surfactant of following formula (f) structure.By its properties of Aqueous Solution result of study is shown, this tensio-active agent has surfactivity, lathering property and bactericidal property preferably.
These above-mentioned documents are all take the cardanol or derivatives thereof as starting raw material, utilize cardanol hydroxyl activity and orientation effect, by common are the machine building-up reactions, have synthesized a series of tensio-active agents.And major part is all anionic or nonionic surface active agent, and be the list tensio-active agent, only there is CN102728272 A to synthesize a class list cationic surfactant, although be the orientation effect that utilizes phenolic hydroxyl group equally, introduce cation group on the phenolic hydroxyl group ortho position, but the preparation process of this tensio-active agent is complicated, needs through two-step reaction, the treating processes of while product is relative complex also, causes productive rate not high; And the tensio-active agent for preparing is list.
Simultaneously, along with day by day widening of cardanol Application Areas,, cardanol derivative that have excellent properties novel for obtaining still has the demand of needing badly, and this is also important topic and the emphasis of the research aspect of deeply becoming more meticulous of current cardanol.
Summary of the invention
Technical problem solved by the invention is: provide a kind of novel cardanol cationic quaternary ammonium Salt And Preparation Method, in preparation process, utilize activity and the orientation effect of phenolic hydroxyl group, two step synthesis has obtained described cationic quaternary ammonium salt, avoid on the one hand polystep reaction to cause the defective of the low and product purifying technique complexity of the yield of the finished product, overcome on the other hand the defective on the list surfactant properties.
The technical solution adopted in the present invention is:
The invention provides a kind of cationic quaternary ammonium salt of cardanol of novel following formula (I) structure:
In formula (I): R
1, R
2, R
3Identical or different separately, be independently selected from methyl, ethyl or propyl group; X is halogen, for example can be F, Cl, Br or I.
The invention provides the preparation method of the cationic quaternary ammonium salt of above-mentioned formula (I) cardanol: at first cardanol and formaldehyde are reacted and make the cardanol intermediate, then with cardanol intermediate, tertiary amine (II) NR
1R
2R
3(hereinafter to be referred as " tertiary amine ") and epoxyhalopropane (hereinafter to be referred as " epoxyhalopropane ") react and make, wherein R
1, R
2, R
3Described as defined above, its reaction formula is as follows:
Particularly, described preparation method comprises the steps:
(1). cardanol and formaldehyde are joined in reactor for 2:1 according to the molar fraction ratio, pass into rare gas element, adding volume fraction is 40% solvent hexanaphthene, reacts 5h under reflux conditions, reaction mixture is underpressure distillation 6h under 60 ℃, 300 Pa, obtains the cardanol intermediate;
(2). cardanol intermediate, tertiary amine and epoxyhalopropane are added in reactor, pass into rare gas element, add lower alcohol, reaction obtains mixture;
(3). with the mixture underpressure distillation that step (2) obtains, remove reaction solvent and unreacting material, obtain solid;
(4). the solid organic solvent washing with step (3) obtains, filter, obtain white solid, drying under reduced pressure, obtain the cationic quaternary ammonium salt of cardanol of the present invention subsequently.
In order to describe in more detail preparation method of the present invention, following feature in each step and/or key element are described, but are appreciated that this is not is any restriction that the present invention is made, and only be used for the use that exemplifies.
In described step (2):
Described rare gas element can be nitrogen;
Described lower alcohol is C
1-C
6Alcohol, as methyl alcohol, ethanol, n-propyl alcohol, Virahol, propyl carbinol, sec-butyl alcohol, isopropylcarbinol, the trimethyl carbinol, Pentyl alcohol, n-hexyl alcohol etc., the ratio of the volume of its volume and three kinds of reaction raw materials (being cardanol, tertiary amine and epoxyhalopropane) is 2-4:1, for example can be 2:1,3:1 and 4:1.
The mol ratio of described cardanol, tertiary amine and epoxyhalopropane can be selected in wide region, but in order to react completely, can make tertiary amine and epoxyhalopropane excessive, for example the mol ratio of cardanol, tertiary amine and epoxyhalopropane can be 1:1-5:1-5, for example can be 1:1-4:1-4,1:2-3:2-3;
Temperature of reaction in this step is 40-70 ℃, for example 40 ℃, 45 ℃, 50 ℃, 55 ℃, 60 ℃, 65 ℃ and 70 ℃.Reaction times as 5-10 h, for example can be 5 h, 6 h, 7 h, 8 h, 9 h and 10 h for reaction is completed the needed time.
In described step (3):
The temperature of described underpressure distillation is 50-70 ℃, is for example 50 ℃, 55 ℃, 60 ℃, 65 ℃ and 70 ℃;
The pressure of described underpressure distillation is 100-400 Pa, is for example 100 Pa, 150 Pa, 200 Pa, 250 Pa, 300 Pa, 350 Pa and 400 Pa.
In described step (4):
Described washing does not limit especially with organic solvent, as long as it is lysate in a large number, can exemplify letones, Ester, ether material, aromatic hydrocarbon substance etc. to indefiniteness, for example can be acetone, butanone, ethyl acetate, ethyl formate, methyl acetate, butylacetate, ether, methyl ethyl ether, tetrahydrofuran (THF), chloroform, perhaps any two kinds of multiple mixtures in them; Available described organic solvent washing repeatedly, exemplarily as 1-4 time, for example 1 time, 2 times, 3 times and 4 times.
The pressure of described drying under reduced pressure is 100-400 Pa, is for example 100 Pa, 150 Pa, 200 Pa, 250 Pa, 300 Pa, 350 Pa or 400 Pa;
The temperature of described drying under reduced pressure is 50-70 ℃, is for example 50 ℃, 55 ℃, 60 ℃, 65 ℃ or 70 ℃.
The beneficial effect that the present invention has is: the cationic quaternary ammonium salt of cardanol of the present invention has excellent surfactivity, and its preparation method is simple, raw materials cost is lower, reactions steps is simple, and product is purified easily.The cationic quaternary ammonium salt useful as surfactants of described cardanol of the present invention has good prospect on industrial application.
Description of drawings
Fig. 1 is the building-up reactions equation of cardanol intermediate;
Fig. 2 is the infrared spectra schematic diagram of cardanol intermediate;
Fig. 3 is the infrared spectra schematic diagram of the cationic quaternary ammonium salt of cardanol in embodiment 1,2 and 3;
Fig. 4 is the relation curve schematic diagram of surface tension and concentration during 25 ℃ of cardanol cationic quaternary ammonium salt brine solution in embodiment 1,2 and 3;
Fig. 5 is the infrared spectra schematic diagram of the cationic quaternary ammonium salt of cardanol in embodiment 4;
Fig. 6 is the relation curve schematic diagram of surface tension and concentration during 25 ℃ of cardanol cationic quaternary ammonium salt brine solution in embodiment 4;
Fig. 7 is the infrared spectra schematic diagram of the cationic quaternary ammonium salt of cardanol in embodiment 5;
Fig. 8 is the relation curve schematic diagram of surface tension and concentration during 25 ℃ of cardanol cationic quaternary ammonium salt brine solution in embodiment 5;
Fig. 9 is (I) and (f) the relation curve schematic diagram of surface tension and concentration during 25 ℃ of two kinds of cationic quaternary ammonium salt brine solutions in embodiment 6.
Embodiment
The present invention is described in detail below by specific embodiment:
Add 30g(0.1mol in the reactor of water trap is housed) cardanol and 30mL hexanaphthene, pass into N
2Stir, under 50 ℃, slowly drip the formalin 4.12g of volume fraction 37%, dropwise, be warming up to 85 ℃, back flow reaction 5h.After reaction finished, underpressure distillation 6h under 60 ℃, 300 Pa obtained the cardanol intermediate, and yield is 98%, reaction equation such as Fig. 1.The infrared spectra of cardanol intermediate is seen Fig. 2.Be 3356cm in wave number
-1The charateristic avsorption band of phenolic hydroxyl group has appearred in the place, is 3012cm in wave number
-1Place and 1654cm
-1The charateristic avsorption band of C=C on the side chain has appearred in the place, is about 2950 cm in wave number
-1With 2821 cm
-1The place has occurred-CH
2-charateristic avsorption band, wave number is about 1510 cm
-1The place is the charateristic avsorption band of phenyl ring.
Add 15 g cardanol intermediates (0.025 mol) in reactor, Trimethylamine 99 ethanolic soln 14 g of 5.5 g epoxy chloropropane (0.06 mol) and mass concentration 33% (Trimethylamine 99 is 0.075 mol) and 10 g dehydrated alcohols pass into N
2Stir, isothermal reaction 6 h in the time of 50 ℃, stopped reaction.60 ℃, 266.6 Pa underpressure distillation, desolventizing and unreacted Trimethylamine 99 and epoxy chloropropane get the lightpink solid with reaction mixture.This solid obtains white solid with 45 mL washing with acetone three times; With this solid dry 8 h under 65 ℃, 266.6 Pa vacuum conditions, obtain the white solid powder, active matter content is 85%.Its infrared absorpting light spectra adopts drop-volume method to measure the synthetic surface tension of cationic quaternary ammonium salt aqueous solution in the time of 25 ℃ that obtains under this condition as shown in Figure 3, and its surface tension is seen Fig. 4 with the variation relation curve of concentration.
Infrared spectra Fig. 2 of Fig. 3 and cardanol intermediate relatively can find out, Fig. 3 is 1048 cm in wave number
-1With 1301 cm
-1The charateristic avsorption band of quaternary ammonium salt has appearred in the place, is 1095 cm in wave number
-1The strong charateristic avsorption band of ehter bond C-O-C has appearred in the place, is 1140 cm in wave number
-1The charateristic avsorption band of alcoholic extract hydroxyl group C-O has appearred in the place, and wave number is 1265 cm
-1The charateristic avsorption band of the phenolic hydroxyl group C-O of place disappears, and the characteristic peak of phenyl ring and alkyl still exists.The result demonstration of Fig. 4, in the time of 25 ℃, the micelle-forming concentration cmc of cationic quaternary ammonium salt is 4.85 mmol/L, the surface tension γ of the aqueous solution under this concentration
cmcBe 29.5 mN/m.
Embodiment 3
Adding 15 g cardanol intermediates (0.025 mol), 6.6 g epoxy chloropropane (0.075 mol) and mass concentration in reactor is 33% Trimethylamine 99 methanol solution 14 g (Trimethylamine 99 is 0.075 mol) and 9.6 g anhydrous methanols, passes into N
2Stir, isothermal reaction 6 h in the time of 50 ℃, stopped reaction.Reaction mixture is 60 ℃, 266.6 Pa underpressure distillation, and desolventizing and unreacted Trimethylamine 99 and epoxy chloropropane get the lightpink solid.This solid with 45 mL washing with acetone three times, is obtained white solid; With this solid dry 10 h under 65 ℃, 266.6 Pa vacuum conditions, obtain the white solid powder, active matter content is 83%.Its infrared absorption spectrum is seen Fig. 3 (with embodiment 1).Surface tension when adopting drop-volume method to measure 25 ℃ of the synthetic cationic quaternary ammonium salt aqueous solution that obtains under this condition, its surface tension is seen Fig. 4 (with embodiment 1) with the variation relation curve of concentration.
Embodiment 4
Adding 15 g cardanol intermediates (0.025 mol), 7.9 g epoxy chloropropane (0.01 mol) and mass concentration in reactor is 33% Trimethylamine 99 n-propyl alcohol solution 27 g (Trimethylamine 99 is 0.15 mol) and the anhydrous n-propyl alcohol of 11 g, passes into N
2Stir, isothermal reaction 10 h in the time of 65 ℃, stopped reaction.Reaction mixture is 60 ℃, 266.6 Pa underpressure distillation, and desolventizing and unreacted Trimethylamine 99 and epoxy chloropropane get the lightpink solid.This solid with 45 mL washing with acetone three times, is obtained white solid; With this solid dry 8 h under 65 ℃, 266.6 Pa vacuum conditions, obtain the white solid powder, active matter content is 87%.Its infrared absorption spectrum is seen Fig. 3 (with embodiment 1).Surface tension when adopting drop-volume method to measure 25 ℃ of the synthetic cationic quaternary ammonium salt aqueous solution that obtains under this condition, its surface tension is seen Fig. 4 (with embodiment 1) with the variation relation curve of concentration.
Adding 15 g cardanol intermediates (0.025 mol), 5.5 g epoxy chloropropane (0.06 mol) and mass concentration in reactor is 33% triethylamine ethanolic soln 23 g (triethylamine is 0.075 mol) and 10 g dehydrated alcohols, passes into N
2Stir, isothermal reaction 6 h in the time of 50 ℃, stopped reaction.Reaction mixture is 60 ℃, 266.6 Pa underpressure distillation, and desolventizing and unreacted triethylamine and epoxy chloropropane get the lightpink solid.This solid with 45 mL washing with acetone three times, is obtained white solid; With this solid dry 8 h under 65 ℃, 266.6 Pa vacuum conditions, obtain the white solid powder, active matter content is 82%.Its infrared absorption spectrum is seen Fig. 5.Surface tension when adopting drop-volume method to measure 25 ℃ of the synthetic cationic quaternary ammonium salt aqueous solution that obtains under this condition, its surface tension is seen Fig. 6 with the variation relation curve of concentration.
The infrared spectrogram of Fig. 5 and cardanol intermediate relatively can find out, Fig. 5 is 1050 cm in wave number
-1With 1309 cm
-1The charateristic avsorption band of quaternary ammonium salt has appearred in the place, is 1087 cm in wave number
-1The strong charateristic avsorption band of ehter bond C-O-C has appearred in the place, is 1142 cm in wave number
-1The charateristic avsorption band of alcoholic extract hydroxyl group C-O has appearred in the place, and wave number is 1265 cm
-1The charateristic avsorption band of the phenolic hydroxyl group C-O of place disappears, and the characteristic peak of phenyl ring and alkyl still exists.The result demonstration of Fig. 6, in the time of 25 ℃, the micelle-forming concentration cmc of cationic quaternary ammonium salt is 4.75 mmol/L, the surface tension γ of the aqueous solution under this concentration
cmcBe 29.12 mN/m.
Embodiment 6
Adding 15 g cardanol intermediates (0.025 mol), 5.5 g epoxy chloropropane (0.06 mol) and mass concentration in reactor is 33% tripropyl amine ethanolic soln 33 g (tripropyl amine is 0.075 mol) and 10 g dehydrated alcohols, passes into N
2Stir, isothermal reaction 6 h in the time of 50 ℃, stopped reaction.Reaction mixture is 90 ℃, 266.6 Pa underpressure distillation, and desolventizing and unreacted tripropyl amine and epoxy chloropropane get the lightpink solid.This solid with 45 mL washing with acetone three times, is obtained white solid; With this solid dry 8 h under 65 ℃, 266.6 Pa vacuum conditions, obtain the white solid powder, active matter content is 78%.Its infrared absorption spectrum is seen Fig. 7.Surface tension when adopting drop-volume method to measure 25 ℃ of the synthetic cationic quaternary ammonium salt aqueous solution that obtains under this condition, its surface tension is seen Fig. 8 with the variation relation curve of concentration.
The infrared spectrogram of Fig. 7 and cardanol intermediate relatively can find out, Fig. 7 is 1048 cm in wave number
-1With 1303 cm
-1The charateristic avsorption band of quaternary ammonium salt has appearred in the place, is 1092 cm in wave number
-1The strong charateristic avsorption band of ehter bond C-O-C has appearred in the place, is 1142 cm in wave number
-1The charateristic avsorption band of alcoholic extract hydroxyl group C-O has appearred in the place, and wave number is 1265 cm
-1The charateristic avsorption band of the phenolic hydroxyl group C-O of place disappears, and the characteristic peak of phenyl ring and alkyl still exists.The result demonstration of Fig. 8, in the time of 25 ℃, the micelle-forming concentration cmc of cationic quaternary ammonium salt is 4.78 mmol/L, the surface tension γ of the aqueous solution under this concentration
cmcBe 29.17 mN/m.
Embodiment 7
When adopting 25 ℃ of the aqueous solution of the cationic quaternary ammonium salt of the list with similar structures (f) of reporting in the cationic quaternary ammonium salt of cardanol (I) synthetic in embodiment 2 and the patent CN102824876 A of 2012, surfactivity contrasts, prepare the surfactant soln of a series of concentration, surface tension when adopting drop-volume method to measure 25 ℃ of its aqueous solution the results are shown in Figure 9.The result demonstration of Fig. 9, the micelle-forming concentration cmc of the cationic quaternary ammonium salt (I) that in the time of 25 ℃, this patent synthesizes is 4.78 mmol/L, the surface tension γ of the aqueous solution under this concentration
cmcBe 29.17 mN/m; The micelle-forming concentration cmc of the cationic quaternary ammonium salt of list (f) is 4.6 mmol/L, the surface tension γ of the aqueous solution under this concentration
cmcBe 39.28 mN/m.The surfactivity of the cationic quaternary ammonium salt of cardanol (I) that this patent is synthetic is better than the cationic quaternary ammonium salt of list (f).
Claims (9)
1. cationic quaternary ammonium salt of cardanol: structural formula is as shown in the formula (I):
R wherein
1, R
2, R
3Identical or different separately, be independently selected from methyl, ethyl or propyl group; X is halogen.
2. the cationic quaternary ammonium salt of cardanol as claimed in claim 1, it is characterized in that: X is F, Cl, Br or I.
3. the preparation method of the cationic quaternary ammonium salt of the described cardanol of claim 1 is characterized in that: at first cardanol and formaldehyde are reacted and make the cardanol intermediate, then with cardanol intermediate, tertiary amine N R
1R
2R
3React with epoxyhalopropane and make, wherein R
1, R
2, R
3Identical or different separately, be independently selected from methyl, ethyl or propyl group.
4. the preparation method of the cationic quaternary ammonium salt of cardanol as claimed in claim 3, is characterized in that, comprises the steps:
Cardanol and formaldehyde are joined in reactor for 2:1 according to the molar fraction ratio, pass into rare gas element, adding volume fraction is 40% solvent hexanaphthene, reacts 5h under reflux conditions, reaction mixture is underpressure distillation 6h under 60 ℃, 300 Pa, obtains the cardanol intermediate;
Cardanol intermediate, tertiary amine and epoxyhalopropane are added in reactor, pass into rare gas element, add lower alcohol, reaction obtains mixture;
With the mixture underpressure distillation that step (2) obtains, remove reaction solvent and unreacting material, obtain solid;
Solid organic solvent washing with step (3) obtains filters, and obtains white solid, and drying under reduced pressure, namely obtain the cationic quaternary ammonium salt of cardanol of the present invention subsequently.
5. the preparation method of the cationic quaternary ammonium salt of cardanol as claimed in claim 4, it is characterized in that: the described lower alcohol in step (2) is C
1-C
6Alcohol, its volume is (2～4) with the ratio of the volume of three kinds of reaction raw materials: 1, temperature of reaction is 40-70 ℃, the reaction times is 7-10 h.
6. preparation method as described in claim 4 or 5, it is characterized in that: the mol ratio of cardanol intermediate, tertiary amine and epoxyhalopropane is 1:(1-5): (1-5).
7. preparation method as described in claim 4 or 5 is characterized in that: the temperature of underpressure distillation described in step (3) is that 50-70 ℃, pressure are 100-400 Pa.
8. preparation method as described in claim 4 or 5 is characterized in that: washing described in step (4) is one or several mixture in acetone, butanone, ethyl acetate, ethyl formate, methyl acetate, butylacetate, ether, methyl ethyl ether, tetrahydrofuran (THF), chloroform with organic solvent.
9. the cationic quaternary ammonium salt of the described cardanol of claim 1 is as the purposes of tensio-active agent.
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| CN103396306A (en) * | 2013-08-22 | 2013-11-20 | 东北石油大学 | Cardanol Gemini polyoxyethylene ether carboxylate and preparation method thereof |
| CN103920416A (en) * | 2014-05-12 | 2014-07-16 | 江南大学 | Cardanol phenolic-group non-ionic type dimeric surfactant and synthetic method thereof |
| CN104844466A (en) * | 2015-04-02 | 2015-08-19 | 江西科技师范大学 | Cardanol group cationic quaternary ammonium salt, preparation method and application thereof |
| CN105295882A (en) * | 2015-10-27 | 2016-02-03 | 东北石油大学 | Surfactant oil displacing system forming micro emulsion in low critical micelle concentration |
| CN107892671A (en) * | 2017-11-10 | 2018-04-10 | 上海邦高化学有限公司 | Cardanol derivative and application thereof |
| CN112500299A (en) * | 2020-11-27 | 2021-03-16 | 华东理工大学 | Cardanol quaternary ammonium salt type cationic surfactant and application thereof |
| US11008297B2 (en) * | 2017-05-15 | 2021-05-18 | Rowan University | Bio-based, multi-aromatic compounds, and methods of making and using same |
| CN115716779A (en) * | 2022-11-28 | 2023-02-28 | 南京工业大学 | Cardanol-based bisphenol as well as preparation method and application thereof |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103396306A (en) * | 2013-08-22 | 2013-11-20 | 东北石油大学 | Cardanol Gemini polyoxyethylene ether carboxylate and preparation method thereof |
| CN103920416A (en) * | 2014-05-12 | 2014-07-16 | 江南大学 | Cardanol phenolic-group non-ionic type dimeric surfactant and synthetic method thereof |
| CN104844466A (en) * | 2015-04-02 | 2015-08-19 | 江西科技师范大学 | Cardanol group cationic quaternary ammonium salt, preparation method and application thereof |
| CN105295882A (en) * | 2015-10-27 | 2016-02-03 | 东北石油大学 | Surfactant oil displacing system forming micro emulsion in low critical micelle concentration |
| US11008297B2 (en) * | 2017-05-15 | 2021-05-18 | Rowan University | Bio-based, multi-aromatic compounds, and methods of making and using same |
| EP3625200A4 (en) * | 2017-05-15 | 2021-08-04 | Rowan University | Bio-based, multi-aromatic compounds, and methods of making and using same |
| CN107892671A (en) * | 2017-11-10 | 2018-04-10 | 上海邦高化学有限公司 | Cardanol derivative and application thereof |
| CN112500299A (en) * | 2020-11-27 | 2021-03-16 | 华东理工大学 | Cardanol quaternary ammonium salt type cationic surfactant and application thereof |
| CN112500299B (en) * | 2020-11-27 | 2023-07-07 | 华东理工大学 | Cardanol-based quaternary ammonium salt type cationic surfactant and application thereof |
| CN115716779A (en) * | 2022-11-28 | 2023-02-28 | 南京工业大学 | Cardanol-based bisphenol as well as preparation method and application thereof |
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Application publication date: 20130612 |