CN115232035B - Di-tertiary amine bisamide sulfonic acid type surfactant and preparation method and application thereof - Google Patents
Di-tertiary amine bisamide sulfonic acid type surfactant and preparation method and application thereof Download PDFInfo
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- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/13—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
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- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
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- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
Abstract
The invention belongs to the technical field of fine chemical engineering, and relates to a di-tertiary amine bisamide sulfonic acid type surfactant and a preparation method thereof, wherein the molecular structural general formula of the di-tertiary amine bisamide sulfonic acid type surfactant is shown as formula W:
wherein R is H or CH 3 . The di-tertiary amine bisamide sulfonic acid type surfactant is prepared from the following raw materials in parts by mole: the molar ratio of the N-hydrogenated tallow-1, 3-propylene diamine, the alcohol solvent, the 1, 3-propane sultone and the acrylamide (or N, N-dimethylacrylamide) is 1: (13.00-26.00): (1.00-1.15): (2.00-2.15). The bis-tertiary amine bisamide sulfonic acid type surfactant disclosed by the invention has the advantages of easiness in obtaining synthetic raw materials, low production cost and simple production process, and can be used as a low-foam surfactant or an emulsifier.
Description
Technical Field
The invention relates to the technical field of fine chemical engineering, in particular to a di-tertiary amine bisamide sulfonic acid type surfactant, and a preparation method and application thereof.
Background
The disclosure of this background section is only intended to increase the understanding of the general background of the invention and is not necessarily to be construed as an admission or any form of suggestion that this information forms the prior art already known to those of ordinary skill in the art.
The surfactant is a compound which can obviously change the interface state of a solution system by adding a small amount of the surfactant, and is an amphiphilic molecule formed by connecting two groups or chain segments with diametrically opposite hydrophilic and hydrophobic properties at two ends of the same molecule through chemical bonds. The surfactant has good emulsifying, defoaming, wetting, washing, sterilizing, softening, antistatic and other properties, and is growing in the fields of industrial and civil applications due to its special properties.
Low foam surfactants are surfactants that exhibit low foam properties during spray cleaning or other use. The primary purpose of the low foam is to meet the production needs. In the production process of certain products, the generation of foam has an adverse effect, and thus low-foaming or bubble-free surfactant products are desired. For example, non-foaming or low-foaming industrial detergents are used as metal cleaners, metal degreasers, plastic cleaners, etc., and more typical applications are spray cleaners, spray degreasers, high-pressure water rinse additives, ultrasonic cleaners, etc.
For example, the use of low foaming surfactants in metal cleaning is described in the prior art as the use of dow chemical low foaming surfactants in metal cleaning, including polyethers, alkyl glucosides (APG) and alkyl polyether glucosides (AEG); the preparation method of the surfactant of the oleoyl amino acid salt series is also disclosed in the research: firstly, adding grease with the molar ratio of 1 (1.5-5) and amino acid salt or fatty acid with the molar ratio of 1 (1.05-1.5) into a normal pressure reactor with a heating, stirring and temperature regulating device; and then adding a catalyst, fully stirring, heating to control the reaction temperature to 130-190 ℃, reacting for 2-8 hours, finally cooling the reaction temperature to 60-90 ℃, and adding a neutralizing agent to adjust the pH value to 7-8 to obtain the product.
The inventors found that the research of the current low-foam surfactant is mostly focused on the aspects of surfactant formulation and composition, and that the surfactant with single component can play the role of the low-foam surfactant is not much, and the developed varieties are few.
Secondly, at present, sulfonate type surfactants are not developed in large variety and quantity, and are relatively expensive, which limits the wide application, especially the development of low foaming surfactants. In addition, the inventor finds that the existing surfactant still has the defects of low foaming property, poor emulsifying property and complex preparation process technology and method.
Disclosure of Invention
Aiming at the technical problems in the prior art, the invention discloses a di-tertiary amine bisamide sulfonic acid type surfactant and a preparation method thereof, and the prepared di-tertiary amine bisamide sulfonic acid type surfactant has good low foaming property and emulsifying property and simple preparation process, and solves the defects of poor foaming property and emulsifying property and complex preparation process and method of the surfactant in the prior art.
In order to achieve the above object, the technical scheme of the present invention is as follows:
in a first aspect of the present invention, there is provided a bis-tertiary amine bisamide sulfonic acid type surfactant having a molecular structural formula represented by formula W:
in the formula W, R is H or CH 3 。
When R is H, formula W1 is:
when R is CH 3 In the case where formula W2 is:
in a second aspect of the present invention, there is provided a method for preparing the bis-tertiary amine bisamide sulfonic acid type surfactant according to the first aspect, wherein the method comprises the following steps:
mixing N-hydrogenated tallow-1, 3-propylene diamine, an alcohol solvent and 1, 3-propane sultone for reaction to obtain a reaction intermediate M, gradually adding acrylamide (or N, N-dimethylacrylamide) into the reaction intermediate M, and mixing for reaction to obtain W;
the structural formula of the reaction intermediate M is as follows:
C 18 H 37 NHCH 2 CH 2 CH 2 NHCH 2 CH 2 CH 2 5O 3 H。
the reaction route is as follows:
wherein R is H or CH 3 。
In a third aspect of the present invention there is provided the use of a bis-tertiary amine bisamide sulfonic acid surfactant of the first aspect as a low foaming surfactant or emulsifier.
The specific embodiment of the invention has the following beneficial effects:
(a) According to the invention, hydrophilic sulfonic acid groups, amide groups and amine groups are connected with lipophilic groups with a certain carbon chain length in a certain mode, so that the novel surfactant with a chemical structure is formed. Experiments show that the di-tertiary amine bisamide sulfonic acid type surfactant prepared by the invention has good low foaming property, emulsifying property and surface property.
(b) In the prior art, for the sulfonate type surfactant, the adopted sulfonating agent is chlorosulfonic acid, concentrated sulfuric acid, fuming sulfuric acid or sulfur trioxide, and the sulfonating reaction temperature is higher, the preparation process is complex, and the process danger and corrosiveness are higher. The preparation method of the di-tertiary amine bisamide sulfonic acid type surfactant is very simple in process, can be completed by sequentially feeding, mixing and stirring at a lower reaction temperature, does not need high-temperature reaction, greatly reduces energy consumption, reduces operation difficulty of operators, and reduces production cost.
(c) The main raw material of the bis-tertiary amine bisamide sulfonic acid type surfactant is N-hydrogenated tallow-1, 3-propylene diamine, and the raw material is cheap, and the production raw material cost is low.
Drawings
The accompanying drawings, which are included to provide a further understanding of the invention and are incorporated in and constitute a part of this specification, illustrate embodiments of the invention and together with the description serve to explain the invention.
FIG. 1 is a FTIR spectrum of reaction intermediate M after recrystallization and purification.
FIG. 2 is a NMR chart of the reaction intermediate M after recrystallization and purification.
FIG. 3 is a MS spectrum of the reaction intermediate M after recrystallization and purification.
FIG. 4 is a FTIR spectrum of the product W1 after recrystallization and purification.
FIG. 5 is a NMR chart of the product W1 after recrystallization and purification.
FIG. 6 is a MS spectrum of the product W1 after recrystallization and purification.
FIG. 7 is a FTIR spectrum of the product W2 after recrystallization and purification.
FIG. 8 is a graph showing the logarithmic relationship between the surface tension and the concentration of the product W1 after recrystallization and purification.
FIG. 9 is a graph showing the logarithmic relationship between the surface tension and the concentration of the product W2 after recrystallization and purification.
Detailed Description
It should be noted that the following detailed description is illustrative and is intended to provide further explanation of the present application. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs.
It is noted that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of example embodiments in accordance with the present application. As used herein, the singular is also intended to include the plural unless the context clearly indicates otherwise, and furthermore, it is to be understood that the terms "comprises" and/or "comprising" when used in this specification are taken to specify the presence of stated features, steps, operations, devices, components, and/or combinations thereof.
In one embodiment of the invention, a di-tertiary amine bisamide sulfonic acid type surfactant is provided, and the molecular structural general formula of the surfactant is shown as formula W:
in the formula W, R is H or CH 3 。
In one embodiment of the present invention, there is provided a method for preparing the above-mentioned bis-tertiary amine bisamide sulfonic acid type surfactant (formula W), which comprises the following steps:
mixing N-hydrogenated tallow-1, 3-propylene diamine, an alcohol solvent and 1, 3-propane sultone for reaction to obtain a reaction intermediate M, gradually adding acrylamide (or N, N-dimethylacrylamide) into the reaction intermediate M, and mixing for reaction to obtain a di-tertiary amine bisamide sulfonic acid type surfactant W;
wherein the structural formula of the reaction intermediate M is as follows: c (C) 18 H 37 NHCH 2 CH 2 CH 2 NHCH 2 CH 2 CH 2 SO 3 H。
In a specific embodiment, the molar ratio of N-hydrogenated tallow-1, 3-propylene diamine, alcoholic solvent, 1, 3-propane sultone, acrylamide (or N, N-dimethylacrylamide) is 1: (13.00-26.00): (1.00-1.15): (2.00-2.15).
In a specific embodiment, the alcoholic solvent is a low carbon number alcohol, such as ethanol or isopropanol.
In a specific embodiment, the reaction temperature for preparing the reaction intermediate M is 60-80 ℃ and the reaction time is 3-5 hours;
in a specific embodiment, acrylamide (or N, N-dimethylacrylamide) is mixed with the reaction intermediate M at a reaction temperature of 65-75℃for a reaction time of 2-4 hours.
In a preferred embodiment, the preparation method of the bis-tertiary amine bisamide sulfonic acid type surfactant specifically comprises the following steps:
adding N-hydrogenated tallow-1, 3-propylene diamine into a three-neck flask, adding an alcohol solvent, heating, stirring and dissolving, gradually adding 1, 3-propane sultone, and stirring at 60-80 ℃ for reaction for 3-5h after the addition is finished to obtain a reaction intermediate M; then gradually adding acrylamide (or N, N-dimethylacrylamide) into the reaction intermediate M, and stirring and reacting for 2-4 hours at 65-75 ℃ to obtain the di-tertiary amine bisamide sulfonic acid type surfactant W.
In one embodiment of the present invention, there is provided the use of the above-described bis-tertiary amine bisamide sulfonic acid surfactant as a low-foaming surfactant or emulsifier. For example, in industrial cleaners, the production of foam can be detrimental to the control of the manufacturing process and can cause material spillage and environmental pollution problems. For example, in the application of anionic emulsified asphalt, the generation of foam is detrimental to the production and transportation of anionic emulsified asphalt.
In the invention, N-hydrogenated tallow-1, 3-propylene diamine is used as a main reaction raw material of the di-tertiary amine bisamide sulfonic acid type surfactant, and sulfonic acid groups, amide groups and amino groups are introduced into the designed molecular structure of the surfactant by adding raw materials such as 1, 3-propane sultone, acrylamide (or N, N-dimethylacrylamide) and the like in the synthesis step of the di-tertiary amine bisamide sulfonic acid type surfactant, so that the low foaming property, the emulsifying property and the surface property are improved.
In order to enable those skilled in the art to more clearly understand the technical solutions of the present application, the technical solutions of the present application will be described in detail below with reference to specific examples and experimental examples.
Example 1
(1) Preparation of a bis-tertiary amine bisamide sulfonic acid type surfactant represented by formula W1:
1) 326.0g N-hydrogenated tallow-1, 3-propylene diamine and 1100g of isopropyl alcohol were placed in a three-necked flask, and the mixture was heated and dissolved by stirring. Then 128.2g of 1, 3-propane sultone was gradually added, and the mixture was stirred at 70℃for 4 hours to obtain a reaction intermediate M.
The synthetic intermediate M is distilled off the solvent, and then is subjected to infrared, nuclear magnetism and mass spectrometry analysis and detection after being subjected to recrystallization, separation and purification for 3 times by adopting methanol as the solvent.
Infrared analysis (fig. 1): 3464cm -1 (Peak 1) is the stretching vibration peak of O-H in sulfonic acid group, 3026cm -1 (Peak 2) is a secondary amine N-H stretching vibration peak, 2920cm -1 (peak 3) an asymmetric stretching vibration absorption peak of methylene group, 2854cm -1 (peak 4) is symmetrical stretching vibration peak of methylene, 1465cm -1 (peak 5) an asymmetric flexural vibration absorption peak of methylene, 1213cm -1 (peak 6) C-N telescopic vibration absorption peak 1176cm -1 (peak 7) is a symmetrical telescopic vibration absorption peak of sulfonic acid group S=O, 1041cm -1 (peak 8) is an asymmetric telescopic vibration absorption peak of sulfonic acid group S=O, 723cm -1 (peak 9) is a vibration in the methylene basal plane, 605cm -1 (peak 10) is a stretching vibration absorption peak of S-O, 534cm -1 (peak 11) is a bending vibration absorption peak of O-H in the sulfonic acid group.
Nuclear magnetic analysis (fig. 2): 1 H NMR(400MHz,CD 3 OD),δ:0.875-0.910(3H,t,J＝7.0Hz,-CH 3 ),1.219-1.363(30H,s,CH 3 (CH 2 ) 15 CH 2 CH 2 -),1.540-1.647(2H,m,CH 3 (CH 2 ) 15 CH 2 CH 2 -),1.863-1.916(2H,m,-NHCH 2 CH 2 CH 2 NH-),2.005-2.156(2H,m,-CH 2 CH 2 CH 2 SO 3 H),2.847-3.024(8H,m,-CH 2 NHCH 2 CH 2 CH 2 NHCH 2 -),3.468-3.476(2H,t,J＝1.6Hz,-CH 2 SO 3 H)ppm.
mass spectrometry (fig. 3): HRMS (ESI) (positive) M/z: [ M+H ]] + Calcd for C 24 H 53 N 2 O 3 S,449.3777；Found 449.3799。
2) 147.2g of acrylamide is gradually added into the reaction intermediate M, and stirred and reacted for 3 hours at 70 ℃ to obtain the di-tertiary amine bisamide sulfonic acid type surfactant shown in the formula W1.
The solvent of the synthesized product (formula W1) is distilled off, and then the synthesized product is subjected to infrared, nuclear magnetism and mass spectrometry analysis and detection after being subjected to recrystallization, separation and purification for 3 times by adopting methanol as the solvent.
FTIR analysis (see fig. 4): 3445cm -1 (peak 1) is the stretching vibration peak of O-H in the sulfonic acid group, 3209cm -1 (peak 2) is an amide N-H stretching vibration peak, 2918cm -1 (peak 3) asymmetric stretching vibration absorption peak of methylene, 2851cm -1 (peak 4) symmetrical stretching vibration peak of methylene, 1678cm -1 (peak 5) amide C=O stretching vibration absorption peak 1470cm -1 (peak 6) asymmetric flexural vibration of methylene, 1213cm -1 (peak 7) symmetrical telescopic vibration absorption peak of sulfonic acid group S=O, 1184cm -1 (peak 8) is a symmetrical telescopic vibration absorption peak of sulfonic acid group S=O, 1040cm -1 (peak 9) asymmetric stretching vibration absorption peak of sulfonic acid group S=O, 725cm -1 (peak 10) is the vibration absorption peak of the vibration in the methylene basal plane, 608cm -1 (peak 11) is a stretching vibration absorption peak of S-O, 525cm -1 (peak 12) is the flexural vibration absorption peak of O-H in the sulfonic acid group.
NMR analysis (see fig. 5): 1 H NMR(400MHz,CDCl 3 ),δ:0.862-0.896(3H,t,J＝6.8Hz,-CH 3 ),1.256(32H,s,CH 3 (CH 2 ) 16 CH 2 -),1.740(4H,m,-NCH 2 CH 2 CH 2 N-and-CH 2 CH 2 CH 2 SO 3 H),2.196(6H,m,CH 3 (CH 2 ) 16 CH 2 -and-NCH 2 CH 2 CH 2 N-),2.984(6H,t,2×-CH 2 CH 2 CONH 2 and-CH 2 CH 2 CH 2 SO 3 H),3.190(6H,t,-CH 2 CH 2 CH 2 SO 3 H and 2×-CH 2 CH 2 CONH 2 )ppm.
mass spectrometry (see fig. 6): HRMS (ESI) (positive) M/z: [ M+H ] + ] + Calcd for C 30 H 63 N 4 O 5 S,591.4519；Found 591.4480.
The reaction equation is as follows:
example 2
(1) Preparation of bis-tertiary amine bisamide sulfonic acid type surfactant represented by formula W2:
1) 326.0g N-hydrogenated tallow-1, 3-propylene diamine and 1100g of isopropyl alcohol were placed in a three-necked flask, and the mixture was heated and dissolved by stirring. Then 128.2g of 1, 3-propane sultone was gradually added, and the mixture was stirred at 70℃for 4 hours to obtain a reaction intermediate M.
2) 205.2g of N, N-dimethylacrylamide were gradually added to the reaction intermediate M and reacted at 70℃with stirring for 3h. Thus obtaining the di-tertiary amine bisamide sulfonic acid type surfactant shown in the formula W2.
The solvent of the synthesized product (formula W2) is distilled off, and then the synthesized product is subjected to infrared analysis and detection after 3 times of recrystallization, separation and purification by adopting methanol as the solvent.
FTIR analysis (see fig. 7): 3460cm -1 (peak 1) is the stretching vibration peak of O-H in sulfonic acid group, 2918cm -1 (peak 2) asymmetric stretching vibration absorption peak of methylene, 2853cm -1 (peak 3) symmetrical stretching vibration peak of methylene, 1641cm -1 (peak 4) amide C=O stretching vibration absorption peak 1470cm -1 (peak 5) asymmetric flexural vibration of methylene, 1213cm -1 (peak 6) symmetrical telescopic vibration absorption peak of sulfonic acid group S=O, 1163cm -1 (peak 7) is a symmetrical telescopic vibration absorption peak of sulfonic acid group S=O, 1038cm -1 (peak 8) is an asymmetric stretching vibration absorption peak of sulfonic acid group S=O, 721cm -1 (peak 9) is the vibration absorption peak of the vibration in the methylene basal plane, 608cm -1 (peak 10) is a stretching vibration absorption peak of S-O, 525cm -1 (peak 11) is the flexural vibration absorption peak of O-H in the sulfonic acid group.
The reaction equation is as follows:
experimental example 1
The foam inhibition performance of the bis-tertiary amine bisamide sulfonic acid type surfactants prepared in example 1 (formula W1) and example 2 (formula W2) was measured before and after purification, respectively.
The testing method comprises the following steps: at room temperature, 10mL of sodium dodecyl benzene sulfonate (LBS) with mass fraction of 0.5% and a certain amount of sample are poured into a 100mL cylinder with stopper, the stopper is plugged, and the total volume V of foam recorded immediately after 20 times of intense shaking is taken 1 . The bubble suppression value P was calculated according to the following formula, and its size reflects the bubble suppression capability of the sample.
P＝(V 0 -V 1 )/V 0
Wherein V is 0 Total foam volume immediately after shaking in the blank test, mL; v (V) 1 To total foam volume immediately after shaking when the sample was added, mL.
Experimental results: the bis-tertiary amine bisamide sulfonic acid type surfactants prepared in example 1 (formula W1) and example 2 (formula W2) were compared with OP-10, and the foam inhibition properties before and after purification of each product and OP-10 are shown in tables 1-2.
TABLE 1 foam inhibition Properties of samples and OP-10 before purification
TABLE 2 foam inhibition Properties of samples and OP-10 after purification
The experimental results show that: the bis-tertiary amine bisamide sulfonic acid type surfactant prepared in example 2 (formula W2) has a certain foam inhibition capability before and after purification.
Experimental example 2
This experimental example was conducted to determine the emulsifying ability of the bis-tertiary amine bisamide sulfonic acid type surfactants prepared in example 1 (formula W1) and example 2 (formula W2), before and after purification of the products.
The testing method comprises the following steps: at room temperature, 20mL of a sample with the mass fraction of 0.1% and OP-10 aqueous solution and 20mL of liquid paraffin are poured into a 100mL cylinder with a stopper, the stopper is plugged, the sample is vigorously shaken for 5 times and then is left for 1min, and the time for separating 10mL of water is recorded after repeating for 5 times.
Experimental results: the bis-tertiary amine bisamide sulfonic acid type surfactants prepared in example 1 (formula W1) and example 2 (formula W2) were compared with OP-10, and the emulsifying capacity of each product before and after purification and OP-10 are shown in Table 3.
TABLE 3 emulsifying capacity of the surfactants
The experimental results show that: the bis-tertiary amine bisamide sulfonic acid surfactants prepared in example 1 (after purification) and example 2 (before purification) all have good emulsifying ability.
Experimental example 3
This experimental example was conducted on the foaming property and foam stability of the bis-tertiary amine bisamide sulfonic acid type surfactants prepared in example 1 (formula W1) and example 2 (formula W2), and the foaming property and foam stability of the purified products were measured.
The testing method comprises the following steps: 80mL of the purified product aqueous solution with a concentration of 0.001mol/L was prepared for use. 20mL of the prepared solution is placed in a 100mL measuring cylinder with a plug, and the temperature is kept constant for 10min in a water bath kettle with the constant temperature of 25 ℃. Shaking the above solution for 20 times, standing in water bath, standingI.e. the initial height of the foam (H 0 ) The method comprises the steps of carrying out a first treatment on the surface of the After 5min the foam height (H 5 ) The method comprises the steps of carrying out a first treatment on the surface of the The time (t 1/2 I.e., half-life). The procedure was repeated 3 times and the average was taken.
Experimental results: the bis-tertiary amine bisamide sulfonic acid surfactants prepared in example 1 (formula W1) and example 2 (formula W2) were compared with sodium dodecylbenzenesulfonate, and the foamability and foam stability of each product after purification and sodium dodecylbenzenesulfonate are shown in table 4.
Table 4 foamability and foam stability of the surfactants
The experimental results show that: the bis-tertiary amine bisamide sulfonic acid type surfactants prepared in example 1 (formula W1) and example 2 (formula W2) had inferior foaming property and superior foam stability after purification, compared with sodium dodecylbenzenesulfonate. The surfactant prepared in example 1 (formula W1) and example 2 (formula W2) is a low foaming surfactant.
Experimental example 4
In this experimental example, the surface tension test was performed on the surfactants prepared in example 1 (formula W1) and example 2 (formula W2), and the surface tension and Critical Micelle Concentration (CMC) of the purified products were measured.
The measuring method comprises the following steps: preparing a series of surfactant aqueous solutions with different concentrations by adopting a K100 type full-automatic surface tension meter (Germany) for measurement, measuring the surface tension by adopting a hanging piece method, and drawing a surface tension-log c curve to obtain CMC and the surface tension (gamma) under the CMC CMC )。
Experimental results: the surface tension versus concentration log graphs of the surfactants prepared in example 1 (formula W1) and example 2 (formula W2) are shown in fig. 8 and 9. As can be seen, the CMC of example 1 (formula W1) was 1.7X10 -5 mol/L, surface tension at CMC (gamma CMC ) 45.40mN/m. The CMC of example 2 (formula W2) was 1.62X10 -5 mol/L, surface tension at CMC (gamma CMC ) Is 43.80mN/m.
Comparative example 1
In this comparative example, a surfactant having the following structure was synthesized from N-hydrogenated tallow-1, 3-propylenediamine, acrylamide, sodium bisulphite, epichlorohydrin:
the foam volume of the purified sample (0.1 g) was 72mL and the foam inhibition value P was 0.14, as measured by the foam inhibition test method. The foam volume of the purified sample (0.05 g) was 81mL and the foam inhibition value P was 0.04. Thus, the foam inhibition performance is poor.
The above description is only of the preferred embodiments of the present invention and is not intended to limit the present invention, but various modifications and variations can be made to the present invention by those skilled in the art. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (9)
1. A di-tertiary amine bisamide sulfonic acid type surfactant is characterized in that the molecular structural general formula of the surfactant is shown as formula W:
in the formula W, R is H or CH 3 。
2. The process for preparing a bis-tertiary amine bisamide sulfonic acid surfactant according to claim 1, wherein the process comprises the steps of:
mixing N-hydrogenated tallow-1, 3-propylene diamine, an alcohol solvent and 1, 3-propane sultone for reaction to obtain a reaction intermediate M, gradually adding acrylamide or N, N-dimethylacrylamide into the reaction intermediate M, and mixing for reaction to obtain a di-tertiary amine bisamide sulfonic acid type surfactant W;
the structural formula of the reaction intermediate M is as follows:
C 18 H 37 NHCH 2 CH 2 CH 2 NHCH 2 CH 2 CH 2 SO 3 H。
3. the preparation method according to claim 2, wherein the mixed reaction temperature for preparing the reaction intermediate M is 60-80 ℃ and the reaction time is 3-5 hours;
the mixed reaction temperature of the acrylamide or the N, N-dimethylacrylamide and the reaction intermediate M is 65-75 ℃ and the reaction time is 2-4h.
4. The method of claim 2, wherein the molar ratio of N-hydrogenated tallow-1, 3-propanediol, alcoholic solvent, 1, 3-propane sultone, acrylamide or N, N-dimethylacrylamide is 1: (13.00-26.00): (1.00-1.15): (2.00-2.15).
5. The method according to claim 2, wherein the alcohol solvent is low-carbon ethanol or isopropanol.
6. The preparation method as claimed in claim 2, comprising the following steps:
adding N-hydrogenated tallow-1, 3-propylene diamine into a three-neck flask, adding an alcohol solvent, heating, stirring and dissolving, gradually adding 1, 3-propane sultone, and stirring at 60-80 ℃ for reaction for 3-5h after the addition is finished to obtain a reaction intermediate M; gradually adding acrylamide or N, N-dimethylacrylamide into the reaction intermediate M, and stirring and reacting for 2-4 hours at 65-75 ℃ to obtain the di-tertiary amine bisamide sulfonic acid type surfactant W.
7. The method for preparing a bis-tertiary amine bisamide sulfonic acid surfactant according to claim 2, wherein the method further comprises: separating and purifying the product; evaporating the solvent from the synthesized product, and recrystallizing with organic solvent to obtain the final product.
8. The method for preparing a bis-tertiary amine bisamide sulfonic acid surfactant as claimed in claim 7, wherein the organic solvent is methanol.
9. Use of a bis-tertiary-amine bisamide sulfonic acid type surfactant according to claim 1 or a bis-tertiary-amine bisamide sulfonic acid type surfactant prepared by the method according to claims 2 to 8 as a low foaming surfactant or emulsifier.
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Citations (5)
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| CN107383391A (en) * | 2017-04-13 | 2017-11-24 | 山东大学 | A kind of secondary amide double quaternary ammonium salt type hydroxypropyl azochlorosulfonate acid sodium asphalt emulsifier and preparation method thereof |
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| CN106947093A (en) * | 2017-04-13 | 2017-07-14 | 山东大学 | A kind of primary amide double quaternary ammonium salt type hydroxypropyl azochlorosulfonate acid sodium asphalt emulsifier and preparation method thereof |
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| CN107383391A (en) * | 2017-04-13 | 2017-11-24 | 山东大学 | A kind of secondary amide double quaternary ammonium salt type hydroxypropyl azochlorosulfonate acid sodium asphalt emulsifier and preparation method thereof |
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