CN113354805B - Modified polyether amine nonionic surfactant, and preparation method and application thereof - Google Patents
Modified polyether amine nonionic surfactant, and preparation method and application thereof Download PDFInfo
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Abstract
The invention relates to the technical field of surfactants, in particular to a modified polyether amine nonionic surfactant, and a preparation method and application thereof. The invention provides a preparation method of a modified polyether amine nonionic surfactant, which comprises the steps of dissolving a polyether amine substance in an organic solvent A to obtain a polyether amine solution; dissolving reducing saccharide in water to obtain reducing saccharide aqueous solution; ultrasonically mixing the polyetheramine solution and the reducing saccharide aqueous solution, and heating and stirring for full reaction to obtain a crude product; and dissolving the crude product in an organic solvent B, and performing cooling recrystallization and rotary evaporation treatment to obtain the modified polyether amine nonionic surfactant. The surfactant obtained by the invention not only has the advantages of higher surface activity, foaming performance, foam stabilizing performance, emulsifying performance, wetting performance and the like than the traditional polyether nonionic surfactant, but also has simpler synthesis process, is suitable for industrial production and has wide application prospect.
Description
Technical Field
The invention relates to the technical field of surfactants, in particular to a modified polyether amine nonionic surfactant, and a preparation method and application thereof.
Background
Surfactants are a class of compounds that contain both hydrophilic and hydrophobic groups within the molecule. It can be aligned on the boundary (surface) surface of the solution. A small amount of surfactant can significantly reduce the surface tension of a solvent (usually water) or change the interfacial state between systems. As an important fine chemical product, the surfactant is rapidly developing, has rich varieties and large demand, and the application field of the surfactant is developed from the traditional fields of daily chemical industry, petroleum exploitation, food addition and the like to the novel high-tech fields of nano materials, medical materials, biotechnology and the like.
Traditional polyether amine nonionic surfactants are widely applied in the fields of spraying, epoxy resin curing agents, gasoline detergents and the like, but the surfactants have the defects of high Critical Micelle Concentration (CMC), and further improvement on foaming performance, foam stabilizing performance, wetting performance, emulsifying performance and the like.
Disclosure of Invention
In order to solve the technical problems, the technical idea of the invention is to synthesize modified polyetheramine nonionic surfactant molecules with a novel structure of a sugar amine Schiff base bond by modifying polyetheramine substances by reducing saccharide substances, so that the Critical Micelle Concentration (CMC) of the surfactant is remarkably reduced, and the foaming performance, foam stabilizing performance, wetting performance and emulsifying performance of the surfactant are improved.
The first purpose of the invention is to provide a modified polyether amine nonionic surfactant, the molecular structure of which is shown as the following formula:
wherein R is
The second purpose of the invention is to provide a method for preparing the modified polyether amine nonionic surfactant, which comprises the following steps:
dissolving the polyether amine substance in an organic solvent A to obtain a polyether amine solution;
dissolving reducing saccharide in water to obtain reducing saccharide aqueous solution;
ultrasonically mixing the polyetheramine solution and the reducing saccharide aqueous solution, and heating and stirring for full reaction to obtain a crude product;
and dissolving the crude product in an organic solvent B, and performing cooling recrystallization and rotary evaporation treatment to obtain the modified polyether amine nonionic surfactant.
The polyether amine substance and the reducing carbohydrate substance used in the invention are both existing compounds, can be prepared from commercially available products or can be prepared by the existing method.
As an embodiment of the invention, the polyetheramine is polyetheramine M2070 (the molecular structure is
)。
In one embodiment of the present invention, the molar ratio of the reducing saccharide substance to the polyether amine M2070 is 1 (1-3).
In one embodiment of the present invention, the temperature of the heating reaction is 50 to 100 ℃.
In one embodiment of the present invention, the heating reaction time is 6 to 48 hours.
In one embodiment of the present invention, the organic solvent a is at least one of methanol, ethanol, isopropanol, n-butanol, and isoamyl alcohol.
In one embodiment of the present invention, the organic solvent B is ethanol.
The third purpose of the invention is to provide the application of the modified polyether amine nonionic surfactant in daily chemical industry, textile washing, food, pesticide preparation and medicine preparation.
The fourth object of the present invention is to provide a detergent containing the modified polyetheramine-based nonionic surfactant.
The invention has the beneficial effects that:
1. the invention uses reducing saccharide substances to modify the polyetheramine substances, and synthesizes a novel glycosyl modified polyetheramine nonionic surfactant. The synthesized glycosyl modified polyether amine nonionic surfactant has a sugar amine Schiff base bond, and has higher surface activity (the critical micelle concentration is reduced to 10) than the traditional polyether amine nonionic surfactant-3Magnitude order) and has the advantages of no toxicity, environmental protection, easy biodegradation, mild property and the like, and is a surfactant with wide application prospect.
2. Compared with the traditional polyether amine nonionic surfactant, the modified polyether amine nonionic surfactant provided by the invention has the advantages that the emulsifying property, the foaming property and the wetting property are obviously improved.
3. The invention provides a preparation method of a modified polyether amine nonionic surfactant, which adopts one-step reaction, can separate crude products by cooling, layering and purifying, has simple preparation process and convenient operation, avoids toxic solvent in the whole process, and can conveniently realize industrial production. The yield of the modified polyether amine nonionic surfactant is generally over 40 percent and can reach 85 percent under the optimized condition, thereby meeting the basic requirements of industrial scale production.
4. The modified polyether amine nonionic surfactant prepared by the invention can be applied to the fields of daily chemical industry, textile washing, food, pesticide preparation, medicine preparation and the like, and meets the current use requirements of more excellent emulsifying property, foaming property and wetting property for the surfactant.
Drawings
FIG. 1 is a Fourier infrared spectrum of a polyetheramine M2070 and a pale yellow liquid obtained in example 1.
FIG. 2 is a Fourier infrared spectrum of a polyetheramine M2070 and a brown liquid obtained in example 3.
FIG. 3 is a gamma-c plot of the results of surface tension tests on the glucose-modified polyetheramine nonionic surfactants prepared in examples 1 and 3 and polyetheramine M2070.
Detailed Description
The present invention will be further described with reference to the following examples. It is to be understood that the following examples are illustrative only and are not intended to limit the scope of the invention, which is to be given numerous insubstantial modifications and adaptations by those skilled in the art in light of the teachings herein.
Example 1 (glucose-modified Polyetheramine nonionic surfactant)
Preparation of glucose-modified polyetheramine nonionic surfactant: 60g (about 30mmol) of polyetheramine M2070 are dissolved in 90mL of ethanol; 1.98g (10mmol) of glucose was dissolved in 50mL of water; and ultrasonically mixing the two solutions, adding the mixture into a 250mL three-neck flask, controlling the temperature to be 50 ℃, and stirring for reaction for 24 hours: it was observed that the solution gradually turned yellowish in color as the reaction proceeded. After the reaction is finished, the obtained crude product is added into ethanol for cooling and recrystallization, 10.06g of light yellow liquid (namely glucose modified polyether amine nonionic surfactant) is obtained through rotary evaporation treatment, and the yield of the glucose modified polyether amine nonionic surfactant is calculated to be 48%.
The results of NMR measurement of the pale yellow liquid obtained in example 1 are as follows:
1H NMR(400MHz,D2O)δ5.29(d,J＝3.7Hz,0.63H),4.70(d,J＝7.9Hz,1.13H),3.92(d,J＝43.6Hz,13.15H),3.77(s,124H),3.67(d,J＝33.5Hz,20.83H),3.55(s,8.74H),3.45(s,5.14H),1.25(dd,J＝9.9,6.8Hz,30.43H),1.12(d,J＝6.5Hz,1.92H)。
mass spectrometry results of the pale yellow liquid obtained in example 1, m/z: 2161.14 is molecular ion peak, which proves that the synthesized substance is glucose modified polyether amine non-ionic surfactant.
The Fourier infrared spectrum of the light yellow liquid obtained by the polyether amine M2070 and the example 1 is shown in the figure 1: wherein 1648cm-1Is a sugar amine Schiff base bond formed by the reaction of polyether amine M2070 and glucose, 3457cm-1The modified polyether amine nonionic surfactant is an OH bond of the modified polyether amine nonionic surfactant.
The specific reaction formula is as follows:
example 2 (glucose-modified Polyetheramine nonionic surfactant)
Preparation of glucose-modified polyetheramine nonionic surfactant: 40g (about 20mmol) of polyetheramine M2070 were dissolved in 100mL of isopropanol; 1.81g (10mmol) of D-anhydroglucose was dissolved in 50mL of water; and ultrasonically mixing the two solutions, adding the mixture into a 250mL three-neck flask, controlling the temperature to be 60 ℃, and stirring for reacting for 48 h: it was observed that the solution color turned slightly yellow as the reaction proceeded. After the reaction is finished, the obtained crude product is added into ethanol for cooling and recrystallization, 16.67g of light yellow liquid (glucose modified polyether amine nonionic surfactant) is obtained through rotary evaporation treatment, and the yield of the glucose modified polyether amine nonionic surfactant is calculated to be 80%.
Example 3 (lactose modified polyetheramine nonionic surfactant)
Preparation of lactose-modified polyetheramine nonionic surfactant: 40g (about 20mmol) of polyetheramine M2070 are dissolved in 100mL of ethanol; 3.80g (10mmol) lactose monohydrate was dissolved in 50mL water; ultrasonically mixing the two solutions, adding the mixture into a 250mL round-bottom flask, controlling the temperature to be 80 ℃, and stirring for reacting for 6 h: it was observed that the solution turned brown in color as the reaction proceeded. After the reaction is finished, the obtained crude product is added into ethanol for cooling and recrystallization, 8.34g of brown liquid (the lactose modified polyether amine nonionic surfactant) is obtained through rotary evaporation treatment, and the yield of the lactose modified polyether amine nonionic surfactant is calculated to be 40%.
The NMR test results of the brown liquid obtained in example 3 are as follows:
1H NMR(400MHz,DMSO)δ3.91(d,J＝196.6Hz,11.76H),3.54(s,14.25H),3.51(s,124H),3.43(d,J＝10.2Hz,20.03H),3.34(dd,J＝26.0,5.2Hz,16.74H),3.24(s,5.07H),1.04(d,J＝6.1Hz,29.62H)。
mass spectrometry results of brown liquid obtained in example 3 m/z: 2341.31 is a molecular ion peak, which proves that the synthesized substance is a lactose modified polyether amine nonionic surfactant.
The Fourier infrared spectra of the polyetheramine M2070 and the brown liquid obtained in example 3 are shown in FIG. 2: 1634cm in it-1Is a glucosamine Schiff base bond formed by the reaction of polyether amine M2070 and glucose, 3532cm-1The modified polyether amine nonionic surfactant is an OH bond of the modified polyether amine nonionic surfactant.
The specific reaction formula is as follows:
example 4 (lactose modified Polyetheramine nonionic surfactant)
Preparation of lactose-modified polyetheramine nonionic surfactant: 20g (about 10mmol) of polyetheramine M2070 were dissolved in 100mL of isopropanol; 3.80g (10mmol) lactose monohydrate was dissolved in 50mL water; and ultrasonically mixing the two solutions, adding the mixture into a 250mL round-bottom flask, controlling the temperature to be 80 ℃, and stirring to react for 24 hours: it was observed that the solution turned brown in color as the reaction proceeded. After the reaction is finished, the obtained crude product is added into ethanol for cooling and recrystallization, 17.71g of brown liquid (the lactose-modified polyether amine nonionic surfactant) is obtained after rotary evaporation post-treatment, and the yield of the lactose-modified polyether amine nonionic surfactant is calculated to be 85%.
Comparative example 1 (glucose-modified polyetheramine-based nonionic surfactant)
Preparation of glucose-modified polyetheramine nonionic surfactant: 20g (about 10mmol) of polyetheramine M2070 were dissolved in 90mL of ethanol; 1.98g (10mmol) of glucose was dissolved in 50mL of water; and ultrasonically mixing the two solutions, adding the mixture into a 250mL three-neck flask, controlling the temperature to be 120 ℃, and stirring for reacting for 72 hours: it was observed that the solution color changed to a yellowish brown color as the reaction proceeded. After the reaction is finished, the obtained crude product is added into ethanol for cooling and recrystallization, and is subjected to rotary evaporation treatment to obtain 4.56g of a yellow-brown liquid, and the yield of the glucose-modified polyether amine nonionic surfactant is calculated to be 21.9%. This is because the reaction temperature is too high and the reaction time is too long, which results in an increase in side reactions.
Comparative example 2 (lactose-modified polyetheramine nonionic surfactant)
Preparation of lactose-modified polyetheramine nonionic surfactant: 20g (ca. 10mmol) of polyetheramine M2070 are dissolved in 90mL of ethanol; 3.80g (10mmol) lactose monohydrate was dissolved in 50mL water; ultrasonically mixing the two solutions, adding the mixture into a 250mL round-bottom flask, controlling the temperature to be 120 ℃, and stirring for reacting for 72 hours: it was observed that the solution color turned to a tan color as the reaction proceeded. After the reaction is finished, the obtained crude product is added into ethanol for cooling and recrystallization, and is subjected to rotary evaporation treatment to obtain 3.17g of yellow brown liquid (the lactose-modified polyether amine nonionic surfactant), and the yield of the lactose-modified polyether amine nonionic surfactant is calculated to be 15.2%. Because the reaction temperature is too high, the reaction time is too long, and side reactions can occur.
Example 5 (surface tension test of surfactant)
Taking unmodified polyetheramine M2070 polyetheramine nonionic surfactant and the modified polyetheramine nonionic surfactants prepared in examples 1 and 3 as examples, the surface tension of the conventional polyetheramine nonionic surfactant and the modified polyetheramine nonionic surfactant of the present invention was tested.
Surface tension test method: the surface tension of the polyetheramine-based nonionic surfactant was measured at various concentrations by platinum plate method at 25.0. + -. 0.1 ℃ using a BZY-2 type surface tension meter. The instrument was calibrated with ultra pure water before measurement. The vessel containing the liquid was placed on the sample table directly under the platinum plate and the reading of the instrument was zeroed. And adjusting the sample stage to enable the solution to slowly rise until the bottom of the platinum plate just contacts with the surface of the solution, and recording the stable reading of the surface tension meter. The platinum gold plate is cleaned, then repeated measurement is carried out, 3 times of continuous measurement are carried out, an average value is taken as a measurement result, and the error of two times of continuous measurement is not more than 0.5 mN/m. The experimental data are shown in table 1 and fig. 3:
table 1 surface tension test results
When the solution reaches the critical micelle concentration (cmc), the surface tension of the solution is reduced to a minimum value, the surfactant concentration is increased, the surface tension of the solution is not reduced any more, but a large number of micelles are formed, and the surface tension of the solution is the minimum surface tension which can be reached by the surfactant. The critical micelle concentration (cmc), which can be a measure of the surfactant surface activity, indicates that the lower the concentration of such an active agent required to form micelles, the lower the concentration to achieve surface saturation adsorption. The lower the concentration required to modify the surface properties to effect wetting, emulsification, solubilization, foaming, etc.
As can be seen from Table 1 and FIG. 1, the critical micelle concentration (cmc) of the unmodified polyetheramine M2070 nonionic surfactant was 10-2mol·L-1While the critical micelle concentration (cmc) of the sugar-based modified polyetheramine nonionic surfactant of the present invention is reduced to 10-3mol·L-1Orders of magnitude. Specifically, the glucose-modified polyetheramine nonionic surfactant prepared in example 1 had a critical micelle concentration (cmc) of about 1/3 for the unmodified polyetheramine M2070 nonionic surfactant; the critical micelle concentration (cmc) of the lactose-modified polyetheramine nonionic surfactant prepared in example 3 was about 1/2 of the unmodified polyetheramine M2070 nonionic surfactant, and the above results demonstrate that the sugar-based modification significantly improves the surface properties of the polyetheramine nonionic surfactant (e.g., polyetheramine M2070 nonionic surfactant).
Example 6 (foaming and foam stabilizing test of surfactant)
Taking unmodified polyetheramine M2070 polyetheramine nonionic surfactant and the modified polyetheramine nonionic surfactants prepared in examples 1 and 3 as examples, the foaming property and the foam stability of the conventional polyetheramine nonionic surfactant and the modified polyetheramine nonionic surfactant of the present invention were verified and tested.
Foaming and foam stability test method of the surfactant: adding 10mL of 1g/L polyether amine nonionic surfactant solution into a 100mL measuring cylinder with a plug, violently shaking for 100 times within 1min, and representing the foamability by using the height of a foam layer when shaking stops, and representing the foamability by using the ratio of the height of the foam layer when shaking stops and standing for 5min to the height of the foam layer when shaking stops. The experimental data are shown in tables 2 and 3 (3 parallel experiments were performed):
TABLE 2 foam height at stop of shaking and foam height at 5min of standing results
| M2070 | Example 1 | Example 3 | |
| When the oscillation stops | 13mm | 40mm | 55mm |
| 5min | 5mm | 35mm | 51mm |
TABLE 3 foamability and foam stability test results
Compared with the unmodified polyether amine M2070 nonionic surfactant, the foaming property and the foam stability of the modified polyether amine nonionic surfactants prepared in the examples 1 and 3 are greatly improved (the foaming property is improved by 2.1 times compared with that of the M2070 in the example 1, the foaming property is improved by 3.2 times compared with that of the M2070 in the example 3, and the foam stability is improved by 1.3 times compared with that of the M2070 in the example 1 and is improved by 1.4 times compared with that of the M2070 in the example 3), wherein the performance of the polyether amine nonionic surfactant with lactose as the glycosyl in the example 3 can be improved to the greatest extent.
Example 7 (emulsification Performance test of surfactant)
Taking unmodified polyetheramine M2070 polyetheramine nonionic surfactant and the modified polyetheramine nonionic surfactants prepared in examples 1 and 3 as examples, the emulsifying performance of the conventional polyetheramine nonionic surfactant and the modified polyetheramine nonionic surfactant of the present invention was verified and tested.
The method for testing the emulsifying property of the surfactant comprises the following steps: pouring 40mL of surfactant aqueous solution with the mass fraction of 0.1% and 40mL of liquid paraffin oil into a 100mL stoppered measuring cylinder, covering a plug, keeping the temperature in a water bath at 25 ℃ for 5min, taking out, shaking vigorously for 5 times, placing the mixture into the water bath at 25 ℃ for standing for 1min, taking out, shaking vigorously for 5 times, repeating the same step for 5 times, standing, starting a stopwatch to time, and recording the time required for 10mL of bottom-layer aqueous phase to separate. Repeating the steps for three times, and calculating an average value. The experimental data are shown in table 4:
table 4 emulsifying Property test results of surfactants
| M2070 | Example 1 | Example 3 | |
| Time of diversion(s) | 239 | 742 | 816 |
Compared with the unmodified surfactant M2070 polyether amine nonionic surfactant, the water separation time of the modified polyether amine nonionic surfactant prepared in the embodiments 1 and 3 is obviously improved, and the longer the water separation time is, the better the emulsifying property is represented, so that the emulsifying property of the polyether amine nonionic surfactant is improved.
Example 8 (wetting Property test of surfactant)
Taking unmodified polyetheramine M2070 polyetheramine nonionic surfactant and the modified polyetheramine nonionic surfactants prepared in examples 1 and 3 as examples, the wetting properties of the conventional polyetheramine nonionic surfactant and the modified polyetheramine nonionic surfactant of the present invention were tested.
Wetting property test method: respectively preparing the surfactant into aqueous solutions with mass concentrations of 1, 5 and 10g/L, and testing the wettability of the surfactant by adopting a canvas settlement method: cutting standard fine canvas into circular pieces (the mass is 0.38-0.39 g) with the diameter of about 35 mm. Respectively putting the canvas into the prepared solution (the solution is contained in a container with the same size specification) according to the same steps, avoiding the canvas from contacting the wall of the container in the sedimentation process so as not to influence the sedimentation result, and recording the time for the canvas to be just completely immersed into the bottom of the container. The results of the experiment are shown in table 5:
TABLE 5 wetting Property test results for surfactants
The settling time of both examples 1 and 3 was reduced after modification, which means that the canvas sheet was more easily wetted, and thus the wetting properties of the modified polyetheramine nonionic surfactants prepared in examples 1 and 3 were significantly improved compared to the unmodified surfactant M2070.
In conclusion, compared with the traditional polyether amine nonionic surfactant, the modified polyether amine nonionic surfactant prepared by the invention has obviously improved emulsifying property, foam property and wetting property. Therefore, the modified polyether amine nonionic surfactant prepared by the invention can be applied to the fields of daily chemical industry, textile washing, food, pesticide preparation, medicine preparation and the like, and meets the current use requirements of more excellent emulsifying property, foaming property and wetting property for the surfactant.
The modified polyether amine nonionic surfactant prepared by the invention has excellent surface performance, so that the modified polyether amine nonionic surfactant can be used as a main component of a detergent to improve the decontamination performance of the existing detergent.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other modifications, changes, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be regarded as equivalent replacements within the protection scope of the present invention.
Claims (10)
1. A modified polyether amine nonionic surfactant is characterized in that the molecular structure is shown as the following formula:
wherein R = is
2. A process for preparing the modified polyetheramine nonionic surfactant of claim 1, comprising the steps of:
dissolving the polyether amine substance in an organic solvent A to obtain a polyether amine solution;
dissolving reducing saccharide in water to obtain reducing saccharide aqueous solution;
ultrasonically mixing the polyetheramine solution and the reducing saccharide aqueous solution, and heating and stirring for full reaction to obtain a crude product;
and dissolving the crude product in an organic solvent B, and performing cooling recrystallization and rotary evaporation treatment to obtain the modified polyether amine nonionic surfactant.
3. The method of claim 2, wherein the polyetheramine is polyetheramine M2070.
4. The method of claim 3, wherein the molar ratio of the reducing saccharide substance to the polyether amine M2070 is 1 (1-3).
5. The method according to any one of claims 2 to 4, wherein the temperature of the heating reaction is 50 to 100 ℃.
6. The method according to claim 2, wherein the heating reaction time is 6-48 h.
7. The method according to any one of claims 2, 3, 4 and 6, wherein the organic solvent A is at least one of methanol, ethanol, isopropanol, n-butanol and isoamyl alcohol.
8. The method according to claim 2, wherein the organic solvent B is ethanol.
9. The use of the modified polyetheramine nonionic surfactant of claim 1 in textile washing, food, pesticide preparation, pharmaceutical preparation.
10. A detergent characterized by containing the modified polyetheramine-based nonionic surfactant according to claim 1.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003049847A1 (en) * | 2001-12-11 | 2003-06-19 | Rhodia Chimie | Multiple emulsion comprising a gelled internal oil phase |
| CN105419765A (en) * | 2015-11-06 | 2016-03-23 | 西南石油大学 | Glycosyl anionic-nonionic surfactant and method for preparing same |
| CN106432710A (en) * | 2016-08-31 | 2017-02-22 | 天津悦泰石化科技有限公司 | Polyether glucosamine, preparation method and application of polyether glucosamine as main agent of gasoline detergent |
| CN106467725A (en) * | 2015-08-14 | 2017-03-01 | 中石化石油工程技术服务有限公司 | A kind of biomass drilling base liquid, its preparation method and its application |
| CN107670583A (en) * | 2017-10-10 | 2018-02-09 | 合肥工业大学 | A kind of glucosyl group Shuangzi nonionic surfactant, amphoteric surfactant and its synthetic method |
| WO2020247976A1 (en) * | 2019-06-03 | 2020-12-10 | Dropworks, Inc. | Systems and methods for stabilizing emulsions |
-
2021
- 2021-06-17 CN CN202110670410.7A patent/CN113354805B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003049847A1 (en) * | 2001-12-11 | 2003-06-19 | Rhodia Chimie | Multiple emulsion comprising a gelled internal oil phase |
| CN106467725A (en) * | 2015-08-14 | 2017-03-01 | 中石化石油工程技术服务有限公司 | A kind of biomass drilling base liquid, its preparation method and its application |
| CN105419765A (en) * | 2015-11-06 | 2016-03-23 | 西南石油大学 | Glycosyl anionic-nonionic surfactant and method for preparing same |
| CN106432710A (en) * | 2016-08-31 | 2017-02-22 | 天津悦泰石化科技有限公司 | Polyether glucosamine, preparation method and application of polyether glucosamine as main agent of gasoline detergent |
| CN107670583A (en) * | 2017-10-10 | 2018-02-09 | 合肥工业大学 | A kind of glucosyl group Shuangzi nonionic surfactant, amphoteric surfactant and its synthetic method |
| WO2020247976A1 (en) * | 2019-06-03 | 2020-12-10 | Dropworks, Inc. | Systems and methods for stabilizing emulsions |
Non-Patent Citations (1)
| Title |
|---|
| Belbekhouche, Sabrina et al.Pullulan-Based Polymer Surfactants for Vinyl Acetate Miniemulsion Polymerization: Kinetics and Colloidal Stability Investigations.《MACROMOLECULAR CHEMISTRY AND PHYSICS》.2015,第216卷(第18期),1879-1887. * |
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