CN108837772A - Dimeric surfactant worm-like micelle systems with pH response - Google Patents
Dimeric surfactant worm-like micelle systems with pH response Download PDFInfo
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- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
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Abstract
Dimeric surfactant worm-like micelle systems with pH response.The invention discloses a kind of electrostatic to construct dimeric surfactant and its rheologic behavio(u)r, belongs to surfactant science and applied technical field.The synthesis of surfactant of the invention includes with stearic acid, thionyl chloride, N1,N1Dimethyl -1,3- propane diamine is starting material, N- (3- (dimethylamino) propyl) stearmide is synthesized, finally with the amide and phthalic acid according to molar ratio 2:1 compounding, obtains the vermiculate glues of final high viscoelasticity.Raw material sources are wide, biorenewable, environmentally protective, and biological degradability is high, enrich the type for the oligo surfactant that renewable resource is raw material, can be widely used in the research of surfactant self-organizing system.
Description
Technical field
The present invention relates to the dimeric surfactant worm-like micelle systems responded with pH, especially a kind of electrostatic is constructed
The dimeric surfactant with pH response constructed by vermiculate glues, belong to surfactant science and application technology and lead
Domain.
Background technique
Surfactant is that a kind of addition minute quantity can significantly decrease the surface tension of solution and be formed in body phase
One substance of orderly molecule aggregate, is made of hydrophobic grouping and hydrophilic radical.Surfactant is because of its amphiphilic nature, both
It can be adsorbed on interface, and ordered aggregation can be formed in certain density solution, therefore have and soak, emulsify, is solubilized,
The performances such as washing, dispersion.In the solution can self-organizing form various orderly molecular aggregates, such as spherical micelle, rod-shaped micelle, compacted
Shellac beam, vesica and liquid crystal etc..The pattern of surfactant aggregates, formation condition and Related Mechanism are always that surface is living
Property agent scientific domain concern and research emphasis.Wherein worm micella occupies an important position in research in recent years.When worm glue
When interfascicular is intertwine with each other with the increase of concentration, dynamic reticular structure will form, and its aqueous solution has viscoplasticity
Matter.Exactly because its this unique property, so that it leads in medicine controlled releasing, bioengineering, microfluid, cosmetics, coating etc.
Domain is widely used.
" quasi- " oligo surfactant is that one kind prepares amphipathic compound that is simple, haveing excellent performance, passes through non-covalent bond phase
It is to constitute the highest method of oligo surfactant efficiency that " quasi- " oligo surfactant is constructed in interaction, avoids many and diverse conjunction
At reaction, and there is lower cmc, higher vicidity, richer self assembly behavior and unique rheological behaviour.This two
The formation for being conducive to worm micella on close molecular structure of compounds is expected to that viscoelasticity stream can be self-assembled under lower dosage
Body.Therefore by non-covalent bond effect construct the research of " quasi- " oligo surfactant self assembly behavior with theoretical research with
Practical value.
Vermiculate glues constructed by dimeric surfactant with pH response refers to the table for the vermiculate glues to be formed
Micelle volume containing the group (such as carboxyl, phenolic hydroxyl group or amido) with pH response in the active agent molecule structure of face, phase
Answer mechanism i.e. by with H+Or OH-Effect causes the variation of surfactant molecule hydrophilic lipophilic balance or participates in micella from group
The structure change of the counter ion of dress leads to vermiculate glues structural damage or reconstruct, to realize that system macroscopic view is viscoelastic
It is controllable to change.
The preparation method of pH response type oligo surfactant is still with by based on complicated synthetic reaction at present, and mesh
Before have pH response type surfactant reported in the literature response not rapid enough, the vermiculate glues viscosity of formation is not high.
Summary of the invention
The present invention high viscoelastic vermiculate glues in order to obtain, enhances the focusing energy of oligomeric ionic surfactant
Power, the present invention have constructed Shuangzi surface with the simple electrostatic attraction of phthalic acid by the enuatrol with 18 chain lengths and have lived
Property agent, form high viscoplasticity vermiculate glues, and its response speed is very fast, the moment viscoplasticity that pH changes is immediately therewith
Variation.
The first purpose of the invention is to provide a kind of dimeric surfactant that electrostatic is constructed, structure is as follows：
It is to provide a kind of preparation method of high viscoelastic vermiculate glues in second purpose of invention, the method is
With N1,N1Dimethyl -1,3- propane diamine, stearic acid are starting material, synthesize N- (3- (dimethylamino) propyl) stearmide,
Finally with N- (3- (dimethylamino) propyl) stearmide and phthalic acid according to molar ratio 2:1 compounding obtains final
With pH response high viscoelasticity vermiculate glues.
In one embodiment of the invention, the preparation method is specially：Life is reacted with thionyl chloride with stearic acid
At stearyl chloride, N1,N1Dimethyl -1,3- propane diamine and stearyl chloride are according to molar ratio 2：1 mixing, generates N- (3- (dimethyl
Amino) propyl) stearmide.N- (3- (dimethylamino) propyl) stearmide and phthalic acid are according to molar ratio 1:2 is mixed
It closes, generates the dimeric surfactant that the final electrostatic with PH response is constructed.
In one embodiment of the invention, the N1,N1The molar ratio of dimethyl -1,3- propane diamine and stearyl chloride
It is 1:1~1:2.
In one embodiment of the invention, the N1,N1Dimethyl -1,3- propane diamine and stearyl chloride substitution reaction
Condition be 60 DEG C~85 DEG C reaction 8-12 hours.
In one embodiment of the invention, N- (3- (dimethylamino) propyl) stearmide and O-phthalic
Acid is according to molar ratio 2:1 is uniformly mixed, and obtains the dimeric surfactant that final electrostatic is constructed.
In one embodiment of the invention, the specific reaction equation of the preparation method is as follows：
The synthetic route for the dimeric surfactant that electrostatic is constructed：
The dimeric surfactant constructed third object of the present invention is to provide the electrostatic with PH response passes through
The solution viscoelasticity of rheology verifying is with pH situation of change.
In one embodiment of the invention, the range of pH regulation is 4-10.
In one embodiment of the invention, it is monotonicallyd increase up in 10 processes with pH by 4, solution appears similar to
The same low viscosity solution of water, high-viscosity gel shape liquid, the heterogeneous suspended liquid status of low viscosity.
Fourth object of the present invention is to have expanded stearic application category.China is large agricultural country, stearic acid yield
Position is at the forefront in the world, and the present invention is renewable resource, environmentally protective stearic acid provides and is widely applied potentiality.
In one embodiment of the invention, the application be applied to environmental area, field of textiles, oilfield exploitation,
Chemical field prepares drug field, industry cleaning link, household chemicals.It in these areas, all can be in need using uniform enough
The high viscoelastic solution of response type scene, for example, the cleaning agent of paint, pharmaceutical preparation etc., accurate device and machine,
To improve " active water " displacement of reservoir oil used in recovery ratio in Petroleum Production, it is considered as " earth cleaning ".
Beneficial effects of the present invention：
(1) dimeric surfactant that electrostatic of the invention is constructed is stearic using stearic 18 carbon as hydrophobic chain
Sour source is wide, and biorenewable is environmentally protective, and biological degradability is high, enriches the biological primary surface that renewable resource is raw material
The type of activating agent can be widely used in the research of surfactant self-organizing system.Using hard with 18 chain lengths
Resin acid is as raw material.If select short carbon chain saturated fatty acid be used as starting material, the self-assembly ability of surfactant and gather
The viscoelasticity energy for the surfactant that collection pattern does not have overlength chain stearic acid as raw material and formed is superior.Specifically, we compare
Under same concentrations (300mM), ten in 12 carbon chain lengths, 14 carbon chain lengths, 16 carbon chain lengths and the present invention
The static rheological data of eight carbon chain lengths compare, it has been found that the surfactant that overlength chain stearic acid is formed as raw material
Viscoplasticity is up to 9.4 × 103Pas, and the surfactant zero-shear viscosity that 12,14,16 carbon chain lengths are formed
Within the scope of 200-1000Pas.
(2) present invention is with stearic acid, N1,N1Dimethyl -1,3- propane diamine is that starting material has synthesized electrostatic is constructed two
Poly- surfactant is the highest method of efficiency, many and diverse synthetic reaction, Er Qiechun is avoided compared to traditional synthesis process
Change process is relatively easy.Final step, which only needs to be added in sample bottle by charge ratio, in the present invention can construct dimerization surface-active
Agent greatly improves yield (100%)；And traditional chemical synthesis route needs repeated recrystallize that can just obtain purer production
Object, yield are lower (about 20%).
(3) present invention mixes N- (3- (dimethylamino) propyl) stearmide with phthalic acid, by original position
A kind of false Gemini surface active agent in situ is successfully prepared with reaction.This vacation Gemini surface active agent shows strong viscoelastic
Property, and it is sensitive to the change in elevation of pH.Under continuous pH variation, the form table of false Gemini surface active agent solution aggregation
Reveal and changes from low viscosity solution, to extremely viscoplasticity vermiculate glues, the continuous morphology to disappear to aggregation.High viscoplasticity intelligence
The research of energy vermiculate glues will actively promote oil field fracturing fluid, fluid drag-reduction agent and temperature resisting agent.In the solution that the present invention obtains
In, solution viscosity is up to 9.4 × 103PaS, and other common vermiculate glues viscoplasticity mostly arrive model between several hundred tens
In enclosing.
(4) there is dimeric surfactant of the invention sensitive pH response performance and the reversible of soda acid double responsiveness to open
It closes, when a small amount of acid or alkali is added dropwise into original solution, solution viscoplasticity changes immediately, and other common sound
Answering property vermiculate glues needs could regulate and control solution viscoplasticity for a long time under agitation.Under continuous pH variation, false Shuangzi
The morphologic appearance of surfactant solution aggregation goes out to disappear from low viscosity solution to extremely viscoplasticity vermiculate glues to aggregation
The continuous morphology of mistake changes, and can realize conducting repeated adhesion elastic endless.To make the economy, quick, low energy consumption invertible switch type stream
Body is expected to obtain more extensive biologic applications.
(5) tertiary amine of two moles of phthalate electrostatical binding protonations of the present invention, forms the structure of dimerization, hydrophobic body
Product further increases, so that Packing parameter P is easier to fall within the scope of 1/2-1/3, is more likely formed long and soft vermiculate glues,
Vermiculate glues, which is mutually wound tridimensional network, makes solution show the viscoplasticity similar to polymer.
(6) it is soft to can be widely applied to cosmetics, mineral flotation agent, textile fabric to dimeric surfactant of the invention
The numerous areas such as agent and antistatic agent and pigment dispersing agent.
Detailed description of the invention
Fig. 1 is the nuclear magnetic resonance 1HNMR spectrogram of N- (3- (dimethylamino) propyl) stearmide；
Fig. 2 is the outside drawing of dimeric surfactant solution PH=4.8,6.5,8.2 at 40 DEG C that electrostatic is constructed；
Fig. 3 is that the static rheological of dimeric surfactant solution PH=4.0,6.5,8.0 at 40 DEG C that electrostatic is constructed is bent
Line chart.
Specific embodiment
Embodiment 1：Dimerization quaternary surfactant synthetic route
The dimeric surfactant that electrostatic is constructed, structural formula are as follows：
The synthetic route for the dimeric surfactant that electrostatic is constructed is as follows：
The preparation method for the dimeric surfactant that electrostatic is constructed is first with stearic acid and thionyl chloride according to molar ratio 1：
2 mixing, generate stearyl chloride.Stearyl chloride and N1,N1Dimethyl -1,3- propane diamine is according to molar ratio 1：2 mixing, generate N-
(3- (dimethylamino) propyl) stearmide.N- (3- (dimethylamino) propyl) stearmide and phthalic acid press charge
Than 2:1 mixing, generates the dimeric surfactant that final electrostatic is constructed.
Embodiment 2：The synthesis of stearyl chloride
Stearic acid (142g 0.5mol) is added in 500ml single port bottle, thionyl chloride (60g 0.5mol) is slowly dripped
Be added in single port bottle, reacted 4 hours at 10 DEG C, after reaction, organic layer is washed with deionized water, after with magnesium sulfate drying have
Machine layer, finally vacuum distillation obtains stearyl chloride sterling.Yield 71%, yield=raw material mole/product molar amount.
Embodiment 3：The synthesis of N- (3- (dimethylamino) propyl) stearmide
By N1,N1Dimethyl -1,3- propane diamine (21.0g, 0.2mol), stearyl chloride (60g, 0.2mol), ethyl alcohol
(200g) is put into 500ml single port bottle, stirs 10 hours after adding at 70 DEG C.Sufficiently after reaction, revolving removes solvent, uses
Ethyl alcohol both obtains N- (3- (dimethylamino) propyl) stearmide with re-crystallizing in ethyl acetate three times).Yield 70%.
Embodiment 4：Dimeric surfactant is constructed
By N- (3- (dimethylamino) propyl) stearmide (0.111g, 3 × 10-4Mol), phthalic acid
(0.0249g, 1.5 × 10-4Mol), ultrapure water (1.864g, 0.104mol) is added in the vial of 10ml.Then it sufficiently stirs
It mixes, obtains the clear solution of dimeric surfactant.
Embodiment 5：The nuclear magnetic resonance of N- (3- (dimethylamino) propyl) stearmide1HNMR spectrum and property
The final product nuclear magnetic resonance 1HNMR spectrum that embodiment 3 obtains is shown in Fig. 1.
According to Fig. 1 nuclear magnetic resoance spectrum map analysis, final product N- (3- (dimethylamino) propyl) stearmide DMSO
Dissolution measures 1HNMR spectrum.In Fig. 1 δ=2.50, at δ=3.30 be DMSO solvent peak.Remaining proton is displaced δ：7.73
(s,1H),3.04(s,2H),2.24(s,2H),2.15(t,6H),2.03(t,2H),1.48(t,4H),1.24(s,28H),
0.85(s,3H).The data cases analysis handled from spectrogram, it can be seen that final product is consistent with design object product.
The dimeric surfactant that electrostatic is constructed is one kind that multiple surfactant molecules are formed by connecting by electrostatic
Novel surfactant.The rheological behavior of aqueous surfactant solution and the micelle type in its aqueous solution are closely related.It is single
The conventional surfactant of the single tail of head often forms spherical micelle in weak solution, such micella contributes not the viscosity of aqueous solution
Greatly.The dimeric surfactant that electrostatic is constructed has two hydrophobic carbochains, when changing spacer group chain length, hydrophobic carbon chain lengths
Dimeric surfactant shows a plurality of types of aggregate structures.
2C18PMA-PA is by C18PMA and phthalic acid are with molar ratio 2：The dimerization surface-active that 1 electrostatic attraction is formed
It is that two stearate radicals form side by side that the hydrophobic part of the surfactant of the agent structure, which is approximately considered,.Fig. 2 show different dense
The 2C of degree18The steady state shearing rheological behaviour of PMA-PA, can significantly observe, the system table when concentration reaches 50mM or more
Apparent shear thinning behavior is revealed；The 2C when concentration reaches 300mM18The shear viscosity of PMA-PA is up to 9.4 ×
103Pa.s；It can be seen that N- (3- (dimethylamino) propyl) stearmide and compounding for phthalic acid are available high viscous
The solution of degree.
Above data explanation, N- (3- (dimethylamino) propyl) stearmide occur in aqueous solution with phthalic acid
Positive and negative charge attracts each other, and forms " quasi- " dimeric surfactant, and the surfactant is similar with traditional surfactant,
Molecule easily forms cylindrical-shaped structure, is conducive to surfactant and is self-assembly of vermiculate glues in aqueous solution, with concentration
Increase is mutually wound three-dimensional network-like structure, macroscopically shows viscosity increase.2C18PMA-PA system is in scope of experiment
Do not occur 0 maximum value of η, indicates that the vermiculate glues is still increasing with surfactant concentration increase.
To (pH=4.0) when a drop concentrated hydrochloric acid being added dropwise in constructed dimeric surfactant solution (2mL), solution viscosity
Moment decline is many, and ten times are had dropped in 10s.Molten when if a drop NaOH concentrated solution being added dropwise into solution (pH=8.0)
Tertiary amine is all precipitated in liquid 10s, and system moment becomes heterogeneous suspended liquid status.Fig. 3 is illustrated under equimolar concentration
Static rheological curve graph under pH=4.0,6.5,8.0 (150mmol/L).Illustrate C18PMA and PA is with molar ratio 2:1 electrostatic attraction
The oligo surfactant for the non-covalent bond connection constructed has very sensitive pH stimulating responsive, and its viscosity change is non-
Chang Mingxian.After acid adding, and then alkali is added dropwise into the solution that peracid is added dropwise, viscosity is returned to original viscosity shape in viscosity decline
State (high viscoelastic solution).5 times so on circulate, solution viscosity not a bit decrease or reduction.
Although the present invention has been described by way of example and in terms of the preferred embodiments, it is not intended to limit the invention, any to be familiar with this skill
The people of art can do various change and modification, therefore protection model of the invention without departing from the spirit and scope of the present invention
Enclosing subject to the definition of the claims.
Claims (10)
1. a kind of dimeric surfactant that electrostatic is constructed, which is characterized in that its structure is as follows：
2. the dimeric surfactant that a kind of electrostatic according to claim 1 is constructed, which is characterized in that be with pH response
High viscoelasticity vermiculate glues.
3. the method for preparing the dimeric surfactant that electrostatic of any of claims 1 or 2 is constructed, which is characterized in that with N1,N1-
Dimethyl -1,3- propane diamine, stearic acid are starting material, N- (3- (dimethylamino) propyl) stearmide are synthesized, by N- (3-
(dimethylamino) propyl) stearmide and phthalic acid obtain dimeric surfactant.
4. according to the method described in claim 3, it is characterized in that, the N1,N1Dimethyl -1,3- propane diamine and stearyl chloride
Molar ratio be 1:(1~2).
5. the method according to claim 3 or 4, which is characterized in that the N1,N1Dimethyl -1,3- propane diamine and tristearin
Acyl chlorides substitution reaction condition is 60 DEG C~85 DEG C, is reacted 8-12 hours.
6. according to the method described in claim 3, it is characterized in that, the N- (3- (dimethylamino) propyl) stearmide with
Phthalic acid is according to molar ratio 2:1 is uniformly mixed, and obtains the dimeric surfactant that final electrostatic is constructed.
7. regulating and controlling the method for the viscoelasticity for the dimeric surfactant that electrostatic of any of claims 1 or 2 is constructed, feature exists
In changing the viscoelasticity of dimeric surfactant by addition acid or alkali in the range of pH 4-10.
8. the dimeric surfactant that electrostatic of any of claims 1 or 2 is constructed is in medicine controlled releasing, microfluid, cosmetics, coating
In application.
9. the coating that the dimeric surfactant constructed using electrostatic of any of claims 1 or 2 is prepared, pharmaceutical carrier,
Detergent or cosmetics.
10. the mineral flotation agent being prepared using the dimeric surfactant that electrostatic of any of claims 1 or 2 is constructed is spun
Textured fiber softening agent, antistatic agent or pigment dispersing agent.
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Cited By (6)
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| CN109851521A (en) * | 2019-01-07 | 2019-06-07 | 江南大学 | A kind of dimeric surfactant foam response system with pH response |
| CN110433729A (en) * | 2019-08-22 | 2019-11-12 | 江南大学 | A kind of stable emulsion with pH response performance |
| CN113413830A (en) * | 2021-07-07 | 2021-09-21 | 江南大学 | Amphiphilic-strong-polarity intelligent switching multi-responsiveness emulsion and preparation thereof |
| CN113735933A (en) * | 2021-09-13 | 2021-12-03 | 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 |
| CN114671778A (en) * | 2022-04-01 | 2022-06-28 | 江南大学 | Wormlike micelle formed by surfactant and constructed by acid-base interaction and preparation thereof |
| CN115044363A (en) * | 2022-06-17 | 2022-09-13 | 山东大学 | Preparation method of wormlike micelle-based rare earth element-containing compound luminescent fluid |
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| CN113413830A (en) * | 2021-07-07 | 2021-09-21 | 江南大学 | Amphiphilic-strong-polarity intelligent switching multi-responsiveness emulsion and preparation thereof |
| CN113413830B (en) * | 2021-07-07 | 2022-08-02 | 江南大学 | Amphiphilic-strong-polarity intelligent switching multi-responsiveness emulsion and preparation thereof |
| CN113735933A (en) * | 2021-09-13 | 2021-12-03 | 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 |
| CN114671778A (en) * | 2022-04-01 | 2022-06-28 | 江南大学 | Wormlike micelle formed by surfactant and constructed by acid-base interaction and preparation thereof |
| CN114671778B (en) * | 2022-04-01 | 2023-08-08 | 江南大学 | Vermiform micelle formed by surfactant constructed through acid-base interaction and preparation thereof |
| CN115044363A (en) * | 2022-06-17 | 2022-09-13 | 山东大学 | Preparation method of wormlike micelle-based rare earth element-containing compound luminescent fluid |
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