CN110577486B - Rosin-based CO 2 /N 2 Response type surfactant and preparation method and application thereof - Google Patents
Rosin-based CO 2 /N 2 Response type surfactant and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses rosin-based CO 2 /N 2 The response type surfactant is introduced by maleinization reaction of maleopimaric acid and N, N-dimethyl-1, 3-propane diamine to react with CO 2 The reacted tertiary amine group and epoxy propanol are subjected to esterification reaction to introduce a hydrophilic group, and the prepared MPANG has good surface activity. Dissolving MPANG in water, and introducing CO into water 2 The aqueous solution shows weak acidity, so that tertiary amine is protonated to form tertiary amine salt and has positive charge to become cationic surfactant MPANGH + (ii) a Introduction of N 2 Drive out CO 2 Thereafter, the positively charged tertiary amine salt is deprotonated back to the original tertiary amine state. The invention also discloses the emulsifying property of the surfactant, and CO is introduced 2 The emulsion becomes better after being changed into the cationic surfactant, and the obtained emulsion has better emulsifying property to CO 2 /N 2 Also has good responsiveness. In addition, emulsions stabilized with either nonionic or cationic surfactants can be greatly reduced in surfactant usage, provided charged particles are present.
Description
Technical Field
The invention belongs to the technical field of green surfactants, and particularly relates to rosin-based CO 2 /N 2 A response type surfactant, a preparation method and application thereof.
Background
The traditional emulsion stabilized by amphiphilic compounds is a thermodynamically unstable system, and the cost is increased due to the fact that a large amount of amphiphilic compounds are required to be added to the emulsion to exist stably for a long time; the Pickering emulsion is an emulsion stabilized by solid particles, is a thermodynamic stable system and has better stability; there are generally two types of particles, including asymmetric surfaces, known as amphiphilic Janus particles, and symmetric surfaces, which are organic or inorganic particles with or without grafted functional groups. In addition, ionic surfactants can also be transferred to oppositely charged particles by electrostatic attraction to render the particles surface active to make Pickering emulsions.
With the development of intelligence, smart responsive surfactants capable of reversibly switching between having and not having surface activity under external stimuli have attracted a wide range of attention, and particles adsorbed by these responsive surfactants can respond to external stimuli such as pH, CO 2 Light, heat, and magnetic fields, etc. CO 2 2 Is widely welcomed as an environmental-friendly, nontoxic, cheap and easily removable stimulating factor.
However, in the existing reports, most of CO 2 The responsive surfactants are also prepared from conventional petroleum-based and commercialized surfactants, which not only are harmful to the environment, but also greatly limit the types of surfactants. With the increasing awareness of environmental protection, the development of green and environmentally friendly CO is urgently needed 2 The responsive surfactant replaces petrochemical resources with natural resources. The invention patent with the application number of ' 201810988241.X ' discloses ' rosin-based CO 2 /N 2 Responsive surfactant, its preparation method and application ", its product MPAGN prepared can not be dissolved in water, has no surface activity, only when CO is introduced 2 Then the surfactant is changed into a tertiary amine salt ionic surfactant which can be dissolved in water and has surface activity. The invention is further improved on the basis of the prior art, the prepared product is a water-soluble surfactant with surface activity, and the application range of the rosin-based responsive surfactant can be further expanded.
Disclosure of Invention
The invention aims to provide rosin-based CO 2 /N 2 A responsive surfactant for preparing CO from rosin as raw material and its preparing process and application 2 Responsive surfactants, and their use in emulsions, study the mechanism by which ionic and nonionic surfactants stabilize emulsions in the presence of charged particles.
In order to achieve the purpose, the invention provides the following technical scheme:
rosin-based CO 2 /N 2 The responsive surfactant, abbreviated as MPANG, has the following structural formula:
introducing CO into the aqueous solution of MPANG 2 Later, the nonionic surfactant MPANG will protonate to the cationic surfactant MPANGH + (ii) a Redirected MPANGH + Introducing N into the aqueous solution of 2 Deprotonation of the polymer to convert it back to the nonionic surfactant MPANG, which can be repeated several times; MPANG to CO 2 /N 2 The response process is as follows:
it is a second object of the present invention to provide the rosin-based CO mentioned above 2 /N 2 The preparation method of the response type surfactant comprises the following steps:
(1) performing addition reaction on rosin and maleic anhydride to prepare maleopimaric acid; wherein the mass ratio of the rosin to the maleic anhydride is 1 (1-1.5), for example, the ratio can be 1:1,1:1.1,1:1.2,1:1.3,1:1.4,1: 1.5; acetic acid is used as a solvent, and the reaction temperature is 120-140 ℃, such as 120 ℃, 130 ℃ and 140 ℃; the reaction time is 3-6 h, such as 3h, 4h, 5h and 6h, and the maleopimaric acid is obtained.
(2) Maleopimaric acid and N, N-dimethyl-1, 3-propane diamine are subjected to imidization reaction to generate MPAN, and the chemical formula of the MPAN is shown as the following formula; wherein the mass ratio of the maleopimaric acid to the N, N-dimethyl-1, 3-propane diamine is 1 (1-1.5), for example, the ratio can be 1:1,1:1.1,1:1.2,1:1.3,1:1.4,1: 1.5; ethanol is used as a solvent, and the reaction temperature is 60-80 ℃, such as 60 ℃,70 ℃ and 80 ℃; the reaction time is 4-6 h, such as 4h, 5h, 6 h:
(3) MPAN in Anhydrous BEsterifying alcohol solvent with epoxypropanol in the presence of triethylamine as catalyst to obtain MPANG (rosinyl CO) 2 /N 2 A responsive surfactant; wherein the mass ratio of MPAN to epoxypropanol is 1 (1-1.2), for example, the ratio is 1:1,1:1.1,1: 1.2; the amount of triethylamine catalyst is 0.5-2 wt% of the total mass of reactants, such as 0.5%, 1%, 1.5%, 2%; ethanol is used as a solvent, and the reaction temperature is 60-80 ℃, such as 60 ℃,70 ℃ and 80 ℃; the reaction time is 8-12 h, such as 8h,10h and 12 h.
It is a third object of the present invention to provide the rosin-based CO mentioned above 2 /N 2 The application of the response type surfactant as an emulsifier in the preparation of response type emulsion. And the mechanism of stabilizing the emulsion by ionic and nonionic surfactants is researched under the condition of the existence of charged particles.
MPANG with CO addition 2 /N 2 The conductivity of the solution can be cyclically changed to prove that the surfactant is applied to CO 2 /N 2 Has good responsiveness.
Dissolution of MPANG into CO 2 The emulsion has good emulsifying property after the aqueous solution is changed into the cationic bicarbonate compared with nonionic, has good stability, and is filled with N at 40-60 ℃, such as 40 ℃, 50 ℃ and 60 DEG 2 The stable emulsion can be broken immediately, and CO is introduced again after breaking 2 The stable emulsion can be formed again after shearing, and the particle size is basically consistent with that of the previous time. In addition, the water phase after demulsification can be used for emulsifying a new oil phase after being collected, and the particle size is basically consistent with that of the first emulsification, so that the response type surfactant can be recycled.
0.1-1 wt% such as 0.1 wt%, 0.5 wt%, 1 wt% etc. of charged nanoparticles dispersed in MPANG and MPANGH with different concentrations + In the aqueous solution, the equal volume of the aqueous phase and the oil phase is subjected to high shearing at 8000-15000 rpm, such as 8000rpm, 11000rpm,15000rpm, and the like for 3-10 min, such as 3min,5min,8min,10min, and the like to prepare the emulsion. MPANGH capable of reacting with cation when nanoparticle is negatively charged, such as silica, hectorite, etc + The surfactant required for stabilizing the emulsion is used by the Pickering emulsion obtained by electrostatic attractionThe amount can be greatly reduced compared with the common emulsion (without charged particles); when the nanoparticles are positively charged, such as alumina, calcium carbonate, etc., they can be used in combination with cationic MPANGH + A novel emulsion is obtained through electrostatic repulsion, after a cationic surfactant forms a common emulsion, charged particles are dispersed among emulsion drops, the emulsion is stabilized through electrostatic repulsion, the dosage of the surfactant required by the emulsion can be greatly reduced compared with the common emulsion, and the rule is also suitable for other positively charged particles, the cationic surfactant, other negatively charged particles and anionic surfactant, for example, aluminum oxide is dispersed into cetyl trimethyl ammonium bromide solution, and silicon dioxide is dispersed into lauryl sodium sulfate solution. However, when an emulsion is prepared by dispersing charged particles (whether positive or negative) in a nonionic surfactant MPANG, the charged particles are dispersed between emulsion droplets after the nonionic surfactant forms an emulsion, and the emulsion is stabilized by electrostatic repulsion between the charged particles, the amount of the surfactant required for stabilizing the emulsion by the charged particles can be greatly reduced, and other nonionic surfactants are also suitable, such as silica dispersed in Tween 80 solution.
The raw material of the surfactant prepared by the invention is natural rosin, which accords with the concept of green sustainable development, and the ternary phenanthrene skeleton structure of the rosin, CO, is introduced 2 /N 2 Responsive tertiary amines, surfactants of this kind in CO 2 /N 2 Under stimulation, the catalyst can be reversibly converted between a nonionic surfactant and a cationic surfactant, and CO is introduced 2 The emulsion prepared by the cationic surfactant has better emulsifying property to CO 2 /N 2 Has good responsiveness and the surfactant can be recycled.
The amount of surfactant required to stabilize the emulsion can be greatly reduced when either nonionic or cationic surfactants are added to the charged nanoparticles.
Compared with the prior art, the invention has the beneficial effects that:
(1) the invention combines the structural characteristics of rosin, and through imidization,the esterification and other methods synthesize rosinyl CO 2 /N 2 A responsive surfactant MPANG; dissolving MPANG in water, introducing CO into water 2 Form H 2 CO 3 Protonating MPAGN to form cationic tertiary amine carbonate MPANGH + Introduction of N 2 Post CO 2 Is discharged, MPANGH + Returning to the original tertiary amine state MPANG, this process may be repeated.
(2) Introducing CO into MPAGN aqueous solution 2 MPANGH converted to cationic form + Then, due to the effect of electrostatic repulsion, MPANGH + The emulsifying property of the emulsion is far better than that of MPANG, and the obtained emulsion is also CO-resistant 2 /N 2 Has good responsiveness and can be used for leading MPANGH to be converted at 40-60 DEG C + Introducing N into the stabilized emulsion 2 The emulsion is immediately broken after the emulsion is broken, and CO is introduced again after the emulsion is broken 2 The stable emulsion can be formed again after shearing, and the particle size is basically consistent with that of the previous time. In addition, the water phase after demulsification can be used for emulsifying a new oil phase after being collected, and the particle size is basically consistent with that of the first emulsification, so that the responsive surfactant can be recycled.
(3) Cation MPANGH + The preparation method can be combined with nano silicon dioxide with negative electricity in water through electrostatic action to prepare Pickering emulsion under the condition of high shearing, also can be combined with nano aluminum oxide with positive electricity in water to stabilize emulsion through electrostatic repulsion between a surfactant and charged particles, when the charged particles exist, the amount of the nonionic surfactant required for stabilizing the emulsion can be greatly reduced, after the nonionic surfactant forms the traditional emulsion, the charged particles are dispersed among emulsion drops, and the emulsion is stabilized through the electrostatic repulsion between the charged particles, so that no matter what type of surfactant exists, only the charged particles exist, and the amount of the surfactant required for preparing the emulsion can be greatly reduced.
Drawings
FIG. 1 shows MPANG 1 H NMR spectrum;
FIG. 2MPANG with CO 2 /N 2 Cyclic variation of post conductivity with alternating passes (pure water for comparison);
FIG. 3 is an appearance diagram of the emulsion obtained in example 4;
FIG. 4 is an appearance diagram of the emulsion obtained in example 5.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to the following embodiments of the present invention, and it should be understood that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
Rosin-based CO 2 /N 2 Responsive polymerizable surfactants, abbreviated as MPANG, of MPANG 1 The H NMR spectrum is shown as 1 in FIG. 1 1 The H NMR spectrum shows that the prepared product is the target product. The structural formula is as follows:
example 2
Rosin-based CO 2 /N 2 The synthesis of the responsive surfactant comprises the following steps:
100g (0.33mol, the total amount of abietic acid, neoabietic acid and palustric acid is calculated as 80 percent, 0.265mol) masson pine rosin, 35g (0.357mol) maleic anhydride and 40g acetic acid react for 4 hours at 140 ℃, 100g glacial acetic acid is added after cooling, and the mixture is cooled, crystallized and filtered to obtain the maleopimaric acid.
10g maleopimaric acid is added into a reactor and dissolved in ethanol, and the mixture is stirred for 0.5h at 85 ℃. Dissolving 2.55g N, N-dimethyl-1, 3-propane diamine in ethanol solvent, dropwise adding into the reactor, stirring for 5 hr, cooling, separating white crystal, vacuum filtering, and drying to obtain MPAN
Adding 10g of MPAN into a reactor, dissolving the MPAN into ethanol, stirring the mixture at 85 ℃ for 0.5h, dissolving 2.36g of epoxy propanol into solvent ethanol, dropwise adding the epoxy propanol into the reactor, adding triethylamine (the amount of the triethylamine accounts for 1 wt% of the total mass of reactants) after the dropwise adding is finished, continuously stirring the mixture for 8h, evaporating the solvent, and purifying a crude product by a chromatographic column (methanol: dichloromethane 2:8) to obtain the product MPANG.
The intermediate MPAN is prepared through imidization, and then the target product is prepared through esterification reaction of the intermediate MPAN and epoxy propanol; through the design of the step, the prepared intermediate MPAN has high yield and good purity, and has better economic benefit.
Example 3
Judging the resulting MPANG vs CO by reversible conversion of the conductivity of the MPANG solution 2 /N 2 The responsiveness of (c). CO 2 2 Dissolving in aqueous solution to form H 2 CO 3 The weak acid solution causes protonation of the tertiary amine group to form the charged cationic surfactant MPANGH + The conductivity was increased to about 104.5. mu.s/cm. When N is introduced at 60 DEG C 2 Drive out CO 2 Thereafter, the weak acidity of the solution disappears and the charged cationic surfactant deprotonates back to the original tertiary amine group state, reducing the conductivity back to the original value when the CO is again introduced 2 Thereafter, the conductivity again increased to about 104.5. mu.s/cm, and this process was repeated several times to show that MPANG was responsible for CO 2 /N 2 Has good responsiveness. MPANG to CO 2 /N 2 The response process is as follows:
example 4
7mL of MPANG or MPANGH with different concentrations + Adding 7mL liquid paraffin into the water solution, and high-shearing at 1100rpm for 5min to obtain two kinds of emulsions, as shown in FIG. 3, (A) is emulsion prepared from MPANG with different concentrations, and (B) is MPANG with different concentrations + The obtained emulsion has bottle mouth with figure of MPANG or MPANGH in water solution + Concentration of (4) (mmol/L); as can be seen from FIG. 3, MPANGH + Compared with MPANG, the emulsion has strong emulsifying property and better emulsion stability, and can be used for increasing the emulsion viscosity to MPANG at 60 deg.C + Introducing N into the stable emulsion 2 The stable emulsion will standDemulsifying at once, introducing CO again 2 The stable emulsion can be formed again after shearing, and the particle size is basically consistent with that of the previous time. In addition, the water phase after the emulsion breaking can be collected to emulsify a new oil phase, the particle size is basically consistent with that of the first emulsification, so that the obtained emulsion is also CO-resistant 2 /N 2 Has good responsiveness and the surfactant can be recycled.
Example 5
0.5 wt% nano alumina dispersed in 7mL of MPANG or MPANGH with different concentrations + Adding 7mL liquid paraffin into the water solution, and high shearing at 1100rpm for 5min to obtain two kinds of emulsion, as shown in FIG. 4, (C) is 0.5 wt% Al 2 O 3 Emulsions (D) of 0.5% by weight Al dispersed in MPANG aqueous solutions of different concentrations 2 O 3 Dispersed in MPANGH of different concentrations + The emulsion is prepared from water solution, and the number on the bottle mouth is MPANG or MPANGH + Concentration of (4) (mmol/L); the amount of surfactant required to stabilize the emulsion in the presence of nano-alumina was greatly reduced compared to the emulsion obtained in example 4.
Ionic surfactants and charged particles of the same charge can also stabilize emulsions. The droplet size of Pickering emulsions stabilized with ionic surfactant and oppositely charged particles is much larger than that stabilized with surfactant alone, however, the droplet size of emulsions stabilized with ionic surfactant and similarly charged particles is comparable to that stabilized with surfactant alone because these particles do not participate in the formation of the emulsion but are dispersed in the continuous phase, the mechanism of stabilization being the electrostatic repulsion between the ionic surfactant and the similarly charged particles dispersed between the emulsions.
It has also been found that the amount of surfactant used can be greatly reduced even in the presence of charged particles when the emulsion is stabilized with a nonionic surfactant, the mechanism of stabilization being by electrostatic repulsion between the charged particles dispersed between the emulsions.
Although the present description is described in terms of embodiments, not every embodiment includes only a single embodiment, and such description is for clarity only, and those skilled in the art should be able to integrate the description as a whole, and the embodiments can be appropriately combined to form other embodiments as will be understood by those skilled in the art. Therefore, the above description is only a preferred embodiment of the present application, and is not intended to limit the scope of the present application; all changes which come within the meaning and range of equivalency of the claims are to be embraced within their scope.
Claims (7)
1. Rosin-based CO 2 /N 2 The responsive surfactant, abbreviated as MPANG, has the following structural formula:
2. the rosin-based CO of claim 1 2 /N 2 A responsive surfactant characterized by: introducing CO into the aqueous solution of MPANG 2 Thereafter, MPANG will protonate to cationic MPANG + (ii) a Redirected MPANGH + Introducing N into the aqueous solution of 2 ，MPANGH + Deprotonation back to MPANG; MPANG to CO 2 /N 2 The response process is as follows:
3. the rosin-based CO of claim 1 2 /N 2 The preparation method of the response type surfactant is characterized by comprising the following steps: the method comprises the following steps:
(1) performing addition reaction on rosin and maleic anhydride to prepare maleopimaric acid;
(2) maleopimaric acid and N, N-dimethyl-1, 3-propane diamine are subjected to imidization reaction to generate MPAN, and the structural formula of MPAN is as follows:
(3) MPAN and epoxypropanol are subjected to esterification reaction in an absolute ethyl alcohol solvent to obtain MPANG, namely rosin-based CO 2 /N 2 A responsive surfactant.
4. The production method according to claim 3, characterized in that: in the step (1), the mass ratio of rosin to maleic anhydride is 1 (1-1.5), acetic acid is used as a solvent, the reaction temperature is 120-140 ℃, the reaction time is 3-6 hours, the mixture is added into acetic acid after the reaction is finished and cooled, and the mixture is cooled, crystallized and filtered to obtain the maleopimaric acid.
5. The production method according to claim 3, characterized in that: in the step (2), the mass ratio of the maleopimaric acid to the N, N-dimethyl-1, 3-propane diamine is 1 (1-1.5), ethanol is used as a solvent, the reaction temperature is 60-80 ℃, and the reaction time is 4-6 h.
6. The production method according to claim 3, characterized in that: in the step (3), the mass ratio of MPAN to epoxypropanol is 1 (1-5), triethylamine is used as a catalyst, the mass of triethylamine is 0.5-2 wt% of the total mass of reactants, the reaction temperature is 60-80 ℃, and the reaction time is 8-12 h.
7. The rosin-based CO of claim 1 2 /N 2 The application of the response type surfactant as an emulsifier in the preparation of response type emulsion.
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| CN111109300B (en) * | 2019-12-20 | 2021-05-11 | 广东省石油与精细化工研究院 | PH-responsive rosin/nanoparticle Pickering emulsion and preparation method thereof |
| CN111992132B (en) * | 2020-07-21 | 2022-03-08 | 宁德师范学院 | Composite emulsifier with acid-base regulation and control performance, emulsion and preparation method of composite emulsifier |
| CN112675317B (en) * | 2020-12-24 | 2023-03-14 | 广东药科大学 | CO2/N2 switch type fluorescent liquid-liquid phase separation nano liquid drop and preparation method thereof |
| CN112940070B (en) * | 2021-02-05 | 2023-05-12 | 华侨大学 | Rosin-based dicarboxylate surfactant, preparation method and application thereof |
| CN113735933B (en) * | 2021-09-13 | 2022-10-18 | 中国林业科学研究院林产化学工业研究所 | PH-responsive rosin-based surfactant, preparation method thereof and pseudo-gemini surfactant constructed by same |
| CN114891517B (en) * | 2022-04-29 | 2023-06-23 | 盐城工学院 | Rosin-based CO 2 /N 2 Responsive microemulsion, and preparation method and application thereof |
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