CN109985566B - Mixed system containing fatty acid type surfactant and preparation method thereof - Google Patents
Mixed system containing fatty acid type surfactant and preparation method thereof Download PDFInfo
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Abstract
The invention relates to the field of surfactants, and discloses a mixed system containing a fatty acid type surfactant, which comprises long-chain fatty acid with 11-16 carbon atoms, N, N, N ', N' -tetramethyldiamine and water, wherein the molar ratio of the long-chain fatty acid to the N, N, N ', N' -tetramethyldiamine is 45-205: 100. In another aspect, the present invention discloses a method for preparing a mixed system containing a fatty acid type surfactant, which comprises mixing a long-chain fatty acid having 11 to 16 carbon atoms, N' -tetramethyldiamine and water until the solid is dissolved. In addition, the invention also discloses a mixed system prepared by the method. The mixed system of the present invention can be stably preserved without crystallization even if the long-chain fatty acid is present at a relatively high concentration. Moreover, the formula and the preparation method of the invention are simple and easy to popularize and apply.
Description
Technical Field
The invention relates to the field of surfactants, in particular to a mixed system containing fatty acid type surfactants and a preparation method thereof.
Background
Fatty acid and sodium salt of fatty acid are a kind of surfactant with wide application range, and relates to civil use, oil exploitation, chemical industry and other aspects. The fatty acid surfactant has wide source and low cost, and can be obtained from animal and vegetable fat in large quantity. And the soap used in daily life and chemical production is the fatty acid surfactant, which is healthy and environment-friendly.
Surfactants exist in a variety of aggregated forms in a stable formulation, including true solutions (required below the critical micelle concentration CMC), micelles, worm-like micelles, and lamellar vesicles. The characters reflected in the formula are dilute solution, viscous solution and gel. The aggregation form of the surfactant can be changed by adjusting the components, content and concentration of the formula, so that different properties of the mixture can be realized. Conventional fatty acid surfactants are mostly in the form of their sodium salts. The sodium salt of fatty acid is solid at normal temperature and is easy to phase separate when being miscible with water (the sodium salt of fatty acid is a white solid precipitate, and the upper layer is a clear solution), so that a stable solution system cannot be formed. In recent years, the positive charge quaternary ammonium salt and organic amine are used for solubilizing the fatty acid surfactant, but the obtained solubilizing system can just neutralize the fatty acid to form a stable miscible system only when the molar ratio of the fatty acid to the quaternary ammonium salt (or the organic amine) is 1: 1.
Document Douliez, j.p.; navailes, l.; phase behavior of systems that neutralize Fatty acids with diamines was studied by Nallet, F.Self-Assembly of Fatty Acid-Alkylbodiamine salts.Langmuir 2006,22, 622-. Compared with quaternary ammonium salt and monoamine solubilized fatty acid, diamine solubilized fatty acid has more advantages, a mixed system of various mole ratios of fatty acid to diamine can be obtained, and the composition range of the formula is expanded. However, solubilization of fatty acid-type surfactants with diamines presents an inevitable problem, namely phase-separated crystallization of fatty acids. For example, in Langmuir 2006,22,622-627, when hexadecanoic acid and diamines such as ethylenediamine, butanediamine, hexanediamine, etc. are mixed at a molar ratio of 0.5-2, a fatty acid concentration of 1% (fatty acid/water mass%) can give a mixed solution aggregated in lamellar vesicles. However, even at a low concentration of 1% after standing at room temperature for one day, white crystalline solids appeared in the samples, i.e., crystallization occurred, and the performance properties were impaired. Thus, this disadvantage severely limits the large-scale industrial application of diamine-solubilized fatty acid systems.
Disclosure of Invention
The invention aims to overcome the problem of easy crystallization in the prior art and provide a mixed system containing fatty acid type surfactant and a preparation method thereof.
In order to achieve the above object, the present invention provides, in one aspect, a mixed system containing a fatty acid type surfactant, the mixed system containing a long-chain fatty acid having 11 to 16 carbon atoms, N '-tetramethyldiamine, and water, wherein the molar ratio between the long-chain fatty acid and the N, N' -tetramethyldiamine is 45 to 205: 100.
In another aspect, the present invention provides a method for preparing a mixed system containing a fatty acid-type surfactant, which comprises mixing a long-chain fatty acid having 11 to 16 carbon atoms, N '-tetramethyldiamine and water until the solid is dissolved, wherein the molar ratio between the long-chain fatty acid and the N, N' -tetramethyldiamine is 45 to 205: 100.
In addition, the invention also provides a mixed system prepared by the method.
The mixed system (miscible system) of the present invention can be stably preserved without crystallization even if the long-chain fatty acid is present at a relatively high concentration (at a weight ratio to water of up to 5: 100). Moreover, the formula and the preparation method of the invention are simple and easy to popularize and apply.
Drawings
FIG. 1 is a graph of Differential Scanning Calorimetry (DSC) measurements of a mixed system according to one embodiment of the invention;
FIG. 2 is a chart showing the results of DSC measurement of the mixed system obtained in comparative example 1.
Detailed Description
The endpoints of the ranges and any values disclosed herein are not limited to the precise range or value, and such ranges or values should be understood to encompass values close to those ranges or values. For ranges of values, between the endpoints of each of the ranges and the individual points, and between the individual points may be combined with each other to give one or more new ranges of values, and these ranges of values should be considered as specifically disclosed herein.
The mixed system containing the fatty acid type surfactant comprises a long-chain fatty acid with 11-16 carbon atoms, N, N, N ', N' -tetramethyldiamine and water, wherein the molar ratio of the long-chain fatty acid to the N, N, N ', N' -tetramethyldiamine is 45-205:100, preferably 50-200: 100.
According to the present invention, since the use concentration of the long-chain fatty acid can be increased by blending a specific long-chain fatty acid and a diamine, the weight ratio of the long-chain fatty acid to water may be as high as 5:100, and preferably, the weight ratio of the long-chain fatty acid to water is in the range of 0.1 to 5: 100.
According to the present invention, the long-chain fatty acid is a fatty acid having 11 to 16 carbon atoms, preferably a straight-chain fatty acid including a saturated straight-chain fatty acid and/or an unsaturated straight-chain fatty acid, and more preferably, the long-chain fatty acid is at least one selected from the group consisting of undecanoic acid, 10-undecylenic acid (undecylenic acid), dodecanoic acid (lauric acid), tridecanoic acid, tetradecanoic acid (myristic acid), pentadecanoic acid, and hexadecanoic acid (palmitic acid).
The N, N, N ', N' -tetramethyldiamine can be a common di-tertiary amine, and according to a preferred embodiment of the invention, the N, N, N ', N' -tetramethyldiamine has a formula of (CH)3)2N-(CH2)n-N(CH3)2The diamine is shown, wherein n is 2-10.
More preferably, the N, N, N ', N' -tetramethyldiamine is selected from N, N, N ', N' -tetramethyl-1, 2-ethylenediamine (TMEDA, (CH)3)2N-(CH2)2-N(CH3)2) N, N, N ', N' -tetramethyl-1, 3-propanediamine (TMPDA, (CH)3)2N-(CH2)3-N(CH3)2) N, N, N ', N' -tetramethyl-1, 4-butanediamine (TMBDA, (CH)3)2N-(CH2)4-N(CH3)2) And N, N, N ', N' -tetramethyl-1, 6-hexanediamine (TMHDA, (CH)3)2N-(CH2)6-N(CH3)2) At least one of (1).
The method for preparing the mixed system containing the fatty acid type surfactant comprises the step of mixing long-chain fatty acid with 11-16 carbon atoms, N, N, N ', N' -tetramethyldiamine and water until solid is dissolved, wherein the molar ratio of the long-chain fatty acid to the N, N, N ', N' -tetramethyldiamine is 45-205:100, preferably 50-200: 100.
In the present invention, since the use concentration of the long-chain fatty acid can be increased by blending a specific long-chain fatty acid and a diamine, the weight ratio of the long-chain fatty acid to water may be as high as 5:100, and preferably, the weight ratio of the long-chain fatty acid to water is in the range of 0.1 to 5: 100.
According to the present invention, the long-chain fatty acid is a fatty acid having 11 to 16 carbon atoms, preferably a straight-chain fatty acid including a saturated straight-chain fatty acid and/or an unsaturated straight-chain fatty acid, and more preferably, the long-chain fatty acid is at least one selected from the group consisting of undecanoic acid, 10-undecylenic acid (undecylenic acid), dodecanoic acid (lauric acid), tridecanoic acid, tetradecanoic acid (myristic acid), pentadecanoic acid, and hexadecanoic acid (palmitic acid).
The N, N, N ', N' -tetramethyldiamine can be a common di-tertiary amine, and according to a preferred embodiment of the invention, the N, N, N ', N' -tetramethyldiamine has a formula of (CH)3)2N-(CH2)n-N(CH3)2The diamine is shown, wherein n is 2-10.
More preferably, the N, N, N ', N' -tetramethyldiamine is selected from N, N, N ', N' -tetramethyl-1, 2-ethylenediamine (TMEDA, (CH)3)2N-(CH2)2-N(CH3)2) N, N, N ', N' -tetramethyl-1, 3-propanediamine (TMPDA, (CH)3)2N-(CH2)3-N(CH3)2) N, N, N ', N' -tetramethyl-1, 4-butanediamine (TMBDA, (CH)3)2N-(CH2)4-N(CH3)2) And N, N, N ', N' -tetramethyl-1, 6-hexanediamine (TMHDA, (CH)3)2N-(CH2)6-N(CH3)2) At least one of (1).
In the present invention, the mixing conditions are not particularly limited as long as the long-chain fatty acid is dissolved to form a miscible system. The solution can be accelerated by adopting a mode of standing for a long time, keeping constant temperature after heating, repeatedly heating and cooling, or a physical mode of vortex oscillation, stirring and the like. Preferably, the mixing is carried out at a temperature of 50-90 ℃.
In the present invention, the mixing may be carried out in various conventional manners, and the order of mixing the components is not particularly limited, but in order to avoid volatilization of N, N '-tetramethyldiamine as much as possible and reduce the loss of raw materials, a long-chain fatty acid may be brought into contact with N, N' -tetramethyldiamine, and then water may be introduced.
Further preferably, the mixing mode is as follows: firstly, long-chain fatty acid is contacted with N, N, N ', N' -tetramethyl diamine, then water is introduced, and the mixture is placed at 50-90 ℃ until the solid is dissolved;
or, the mixing mode is as follows: firstly, long-chain fatty acid is contacted with N, N, N ', N' -tetramethyl diamine, then water is introduced, the temperature is raised to 50-90 ℃, the temperature is kept for more than 10min, then the temperature is lowered to room temperature or 0 ℃, the temperature is kept for more than 10min, and the temperature is raised and lowered repeatedly until the solid is dissolved. Unless otherwise stated, "room temperature" is generally in the range of 15 to 25 ℃.
In the above preferred mixing mode, there is no special requirement for the duration of the constant temperature, and the duration can be long or short, and the experimenter can adjust and control according to the actual experimental requirements, but considering that the time is shortened as much as possible, the preparation efficiency is improved, the time of the constant temperature is usually below 72h, and each repetition stage can be the same or different.
In addition, the invention also provides a mixed system prepared by the method.
The fatty acid type surfactant is widely applied to the fields of chemical environmental protection, daily necessities such as laundry detergent (emulsifier and/or stabilizer), tertiary oil recovery (oil displacement agent) and the like, the undecylenic acid can be applied to the fields of medicinal preparations, coating paste for treating onychomycosis and the like, and the mixed system containing the fatty acid type surfactant is not easy to crystallize and can be stably stored, so the fatty acid type surfactant can better play a role in the application.
The present invention will be described in detail below by way of examples.
In the following examples, 10-undecylenic acid was purchased from echiei (shanghai) chemical industry development limited; dodecanoic acid (lauric acid), tetradecanoic acid (myristic acid), hexadecanoic acid (palmitic acid) were purchased from national pharmaceutical group chemicals, ltd; TMEDA, TMPDA, TMBDA, TMHDA, Ethylenediamine (EDA), Propylenediamine (PDA) and N, N' -dimethyl-1, 3-propylenediamine (DMPDA) were purchased from Aladdin reagent.
Examples 1 to 45
Weighing fatty acid according to the dosage shown in the table 1, placing the fatty acid into a sample bottle, adding diamine by using a micro liquid transfer gun, and then adding deionized water; and (3) sealing, heating to a certain temperature (specifically shown in the column of 'temperature' in table 1), keeping the temperature for a certain time (specifically shown in the column of 'constant temperature time' in table 1) until the solid is completely dissolved, and thus obtaining a mixed system sample.
The mixing pattern is shown in Table 1 by the mixing pattern column "1, constant temperature". In table 1, "molar ratio" means a molar ratio between the fatty acid and the diamine, and "weight ratio" means a weight ratio between the fatty acid and water.
Examples 46 to 50
Weighing fatty acid according to the dosage shown in the table 1, placing the fatty acid into a sample bottle, adding diamine by using a micro liquid transfer gun, and then adding deionized water; heating to a certain temperature (see the column of 'temperature' in table 1), keeping constant temperature for a certain time (see the column of 'constant temperature time' in table 1), cooling to room temperature of about 20 deg.C, keeping constant temperature for 10min, and repeatedly heating and cooling for multiple times (see the column of 'constant temperature time' in table 1).
Example 51
Weighing fatty acid according to the dosage shown in the table 1, placing the fatty acid into a sample bottle, adding diamine by using a micro liquid transfer gun, and then adding deionized water; heating to a certain temperature (see the column of 'temperature' in table 1), keeping constant temperature for a certain time (see the column of 'constant temperature time' in table 1), cooling to about 0 deg.C, keeping constant temperature for 10min, and repeatedly heating and cooling for multiple times (see the column of 'constant temperature time' in table 1).
Examples 52 to 56
According to the dosage shown in the table 1, the weighed fatty acid, diamine and deionized water are simultaneously transferred into a sample bottle, and the sample bottle is sealed and heated to a certain temperature (specifically shown in the column of 'temperature' in the table 1) for a certain time (specifically shown in the column of 'constant temperature time' in the table 1) until the solid is completely dissolved, so that a mixed system sample is obtained. This mixing pattern is indicated in table 1 by "2, constant temperature" in the column "mixing pattern".
Comparative example 1
A mixed system containing a fatty acid type surfactant was prepared in the same manner as in example 12, except that the diamine was replaced with the amine-based substance shown in Table 1.
Comparative example 2
A mixed system containing a fatty acid type surfactant was prepared in the same manner as in example 34, except that the diamine was replaced with the amine-based substance shown in Table 1.
Comparative example 3
A mixed system containing a fatty acid type surfactant was prepared in the same manner as in example 34, except that the diamine was replaced with the amine-based substance shown in Table 1.
Comparative example 4
A mixed system containing a fatty acid type surfactant was prepared in the same manner as in example 55, except that the diamine was replaced with the amine-based substance shown in Table 1.
Comparative example 5
A mixed system containing a fatty acid type surfactant was prepared in the same manner as in example 37, except that the diamine was replaced with the amine-based substance shown in Table 1.
TABLE 1
Test example 1
(1) The samples obtained in the above examples and comparative examples were left at room temperature (around 20 ℃ C.) for 24 hours, 72 hours, 1 week, 1 month, and 3 months, and then observed for crystal formation. The observations are shown in table 2 under the column "properties" (showing the properties of each sample at various time points), with visually observed viscosity grades in parentheses:
viscosity is comparable to water: 0
Slightly greater viscosity than water: +
Semi-fluid gel: ++
(2) Phase transition signals (fatty acids) of samples prepared in examples and comparative examples after being left for 3 months were measured at a temperature increase rate of 2 ℃/min using a Differential Scanning Calorimeter (DSC) to determine whether phase separation occurred. Wherein, 10-undecylenic acid and dodecanoic acid which are not subjected to phase separation in an aqueous solution system have no phase transition peak at the temperature of more than 0 ℃; the myristic acid has a phase change peak (peak value at 14 ℃) at 8-16 ℃; hexadecanoic acid had a peak phase transition (peak at 37 ℃) between 33 ℃ and 39 ℃. In the sample without crystallization phase separation, the phase transition peak temperature detected by DSC is equal to or lower than the peak temperature, and the 10-undecylenic acid and the lauric acid which are separated out by phase separation have phase transition peaks at the temperature of more than 0 ℃; the tetradecanoic acid and hexadecanoic acid system which is separated out by phase separation will have a phase transition peak with higher temperature. Thus, the presence or absence of fatty acid crystals was judged. The DSC results of the mixed systems prepared in example 12 and comparative example 1 are shown in FIG. 1 and FIG. 2, respectively. Fig. 1 shows an uncrystallized mixed palmitic acid and TMEDA system, and fig. 2 shows a comparative mixed crystallized palmitic acid and EDA system. The results of DSC measurements of the other examples and comparative examples are shown in Table 2.
TABLE 2
From the above results, it can be seen that the use of N, N' -tetramethyldiamine allows the mixed system of the present invention to be stored stably without crystal precipitation even when left to stand for 3 months, even when the fatty acid is used at a higher concentration (as high as 5:100 in terms of weight ratio to water) than other diamines.
The preferred embodiments of the present invention have been described above in detail, but the present invention is not limited thereto. Within the scope of the technical idea of the invention, many simple modifications can be made to the technical solution of the invention, including combinations of various technical features in any other suitable way, and these simple modifications and combinations should also be regarded as the disclosure of the invention, and all fall within the scope of the invention.
Claims (17)
1. A mixed system containing a fatty acid type surfactant, characterized in that the mixed system contains a long-chain fatty acid having 11 to 16 carbon atoms, N, N, N ', N' -tetramethyldiamine and water, wherein the molar ratio of the long-chain fatty acid to the N, N, N ', N' -tetramethyldiamine is 45 to 205: 100.
2. The mixed system according to claim 1, wherein the molar ratio between the long chain fatty acid and the N, N' -tetramethyldiamine is 50-200: 100.
3. The hybrid system according to claim 1, wherein the weight ratio between the long chain fatty acids and the water is comprised between 0.1 and 5: 100.
4. The mixed system according to any of claims 1-3, wherein the long chain fatty acid is a straight chain fatty acid.
5. The mixing system according to any one of claims 1-3, wherein the long chain fatty acid is selected from at least one of undecanoic acid, 10-undecenoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, and hexadecanoic acid.
6. The hybrid system according to any one of claims 1 to 3, wherein the N, N, N ', N' -tetramethyldiamine has the formula (CH)3)2N-(CH2)n-N(CH3)2And n is 2-10.
7. The hybrid system according to any one of claims 1 to 3, wherein the N, N, N ', N' -tetramethyldiamine is at least one selected from the group consisting of N, N, N ', N' -tetramethyl-1, 2-ethylenediamine, N, N, N ', N' -tetramethyl-1, 3-propanediamine, N, N, N ', N' -tetramethyl-1, 4-butanediamine, and N, N, N ', N' -tetramethyl-1, 6-hexanediamine.
8. A method for producing a mixed system containing a fatty acid type surfactant, which comprises mixing a long-chain fatty acid having 11 to 16 carbon atoms, N, N, N ', N' -tetramethyldiamine and water until a solid is dissolved, wherein the molar ratio of the long-chain fatty acid to the N, N, N ', N' -tetramethyldiamine is 45 to 205: 100.
9. The method of claim 8, wherein the molar ratio between the long chain fatty acid and the N, N' -tetramethyldiamine is 50-200: 100.
10. The method of claim 8, wherein the weight ratio between the long chain fatty acids and water is 0.1-5: 100.
11. The method of any one of claims 8-10, wherein the long chain fatty acid is a straight chain fatty acid.
12. The method of any one of claims 8-10, wherein the long chain fatty acid is selected from at least one of undecanoic acid, 10-undecenoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, and hexadecanoic acid.
13. The method of any one of claims 8-10, wherein the N, N' -tetramethyldiamine has the formula (CH)3)2N-(CH2)n-N(CH3)2And n is 2-10.
14. The method of any one of claims 8-10, wherein the N, N ' -tetramethyldiamine has a structural formula selected from at least one of N, N ' -tetramethyl-1, 2-ethylenediamine, N ' -tetramethyl-1, 3-propanediamine, N ' -tetramethyl-1, 4-butanediamine, and N, N ' -tetramethyl-1, 6-hexanediamine.
15. The method of claim 8, wherein the mixing is performed at a temperature of 50-90 ℃.
16. The method according to any one of claims 8-10, wherein the mixing is performed by: firstly, long-chain fatty acid is contacted with N, N, N ', N' -tetramethyl diamine, then water is introduced, and the mixture is placed at a constant temperature of 50-90 ℃ until the solid is dissolved;
or, the mixing mode is as follows: firstly, long-chain fatty acid is contacted with N, N, N ', N' -tetramethyl diamine, then water is introduced, the mixture is heated to 50-90 ℃ and is kept at the constant temperature for more than 10min, then the mixture is cooled to room temperature or 0 ℃ and is kept at the constant temperature for more than 10min, and the temperature is repeatedly increased and decreased for a plurality of times until the solid is dissolved.
17. A mixed system made by the method of any one of claims 8-16.
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| CN109985564A (en) * | 2017-12-29 | 2019-07-09 | 中国石油化工股份有限公司 | The mixed system and preparation method thereof of fatty acid type surfactant |
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| CN1550257A (en) * | 2003-05-16 | 2004-12-01 | Surfactant package and water in hydrocarbon emulsion using same | |
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