CN108404809B - A kind of application of star-like carboxylic acid group's zwitterionic surfactant as dispersing agent - Google Patents
A kind of application of star-like carboxylic acid group's zwitterionic surfactant as dispersing agent Download PDFInfo
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- CN108404809B CN108404809B CN201810272213.8A CN201810272213A CN108404809B CN 108404809 B CN108404809 B CN 108404809B CN 201810272213 A CN201810272213 A CN 201810272213A CN 108404809 B CN108404809 B CN 108404809B
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- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
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Abstract
A kind of application the invention discloses star-like carboxylic acid group's zwitterionic surfactant as dispersing agent.The dispersing agent is prepared by following steps: quantitative trimethylolpropane-three (3- aziridinyl propionic ester) reaction solution being added dropwise in the reaction flask equipped with long-chain fat primary amine ethanol solution and acidic catalyst and carries out first step aziridine ring-opening reaction；Quantitative chloromethanes (or benzyl chloride) reaction solution is added into reaction solution again and carries out second step quaternary ammonium reaction, products therefrom is a kind of star-like dispersing agent of both sexes for dispersing nanoparticles.Star-like amphoteric dispersant prepared by the present invention, introduces carboxylic acid ion on its strand, and the combination of dispersant molecule and nano particle can be enable fully dispersed in water, enhances the repulsive interaction between graphene particle, increases its dispersion effect.Quaternary ammonium salt cationic is introduced on dispersant molecule chain simultaneously, increases the hydration capability and thermal stability of dispersing agent.
Description
Technical field
The invention belongs to dispersing agent preparation technical fields, and in particular to a kind of star-like carboxylic acid group's zwitterionic surfactant
Application as dispersing agent.
Background technique
Dispersing agent is widely used in each neck as a kind of auxiliary agent that can be improved and improve solid or liquid material dispersion performance
Domain.More multi-field middle needs prepare the material containing partial size smaller particle, particularly with nano material, imitate with quantum size
Answer, small-size effect, skin effect and macro quanta tunnel effect, in catalytic performance, photoelectric properties, magnetoelectric effect and thermal resistance and
Fusing point etc. shows excellent performance.But nano particle is since partial size is small, large specific surface area, is easy to cause reunion, thus
Lose its specific function having.Seriously hinder the industrial applications of nano material.Therefore, often pass through machinery in the prior art
Stirring, ultrasonic disperse or the method for adding auxiliary agent improve the dispersion effect of nano material in the solution.Wherein, mechanical stirring is simple
It is easy, but disadvantage is off the easy secondary agglomeration of nano particle after stirring；Ultra-sonic dispersion method can effectively disperse nanometer
Grain makes it keep dispersion stabilization within a certain period of time, but the application of this method in practical projects, process is complicated, at
This is excessively high, has implemented certain difficulty.
Dispersing agent is added generally also into the material containing nano material to improve the dispersion performance of nano material, but tradition
Dispersing agent performance it is poor, though the dispersion stabilization of nano particle can be maintained, dispersion the retention time it is limited, and tradition dispersion
The pervasive performance of agent is poor, cannot reach good stably dispersing effect eventually, it is suppressed that the use of micro-powder or nano-powder.
Currently, SDS, CMC, CTAB and PVP are most popular dispersing agents, the using effect of these dispersing agents has certain be directed to
Property, if SDS dispersing agent only has preferable stably dispersing effect to nano-titanium dioxide suspension, CMC is only outstanding to nano-graphene
Supernatant liquid has preferable stably dispersing effect, and the dispersion effect and stably dispersing time to other nano particles are poor；Therefore, it now needs
Researching and developing a kind of with broad spectrum activity and can be effectively improved the dispersing agent of nano particle dispersion stabilization.
Summary of the invention
One of the objects of the present invention is to provide a kind of star-like dispersions of the both sexes for dispersing nanoparticles of structure novel
Agent.The second object of the present invention is to provide the preparation method of the dispersing agent.
In order to achieve the above objectives, the present invention uses following technological means:
A kind of application of star-like carboxylic acid group's zwitterionic surfactant as dispersing agent, the dispersion applied to nano particle
In, the structural formula of compound are as follows:
Wherein, R1It is long aliphatic chain, carbon atom number is 12~18 in carbochain.
The mass ratio of dispersing agent and nano particle is 5:25.
The nano particle is nano silica, nanometer calcium carbonate, nano zine oxide and nano aluminium oxide.
The preparation method of star-like carboxylic acid group's zwitterionic surfactant the following steps are included:
(the 3- aziridinyl third of trimethylolpropane-three is added into long-chain fat primary amine ethanol solution and acidic catalyst
Acid esters) reaction solution progress aziridine ring-opening reaction, in 50~80 DEG C of 6~8h of reaction；
It sodium chloroacetate aqueous solution is added under weak basic condition, in Xiang Shangshu reactant carries out carboxyl and replace and quaternary ammoniated anti-
It answers, in 70~90 DEG C of 10~16h of reaction；Insoluble matter is removed after reaction, and concentration of reaction solution is purified with toluene column chromatography
Product is isolated, constant weight is dried under vacuum to and just obtains product.
In aziridine ring-opening reaction, trimethylolpropane-three (3- aziridinyl propionic ester) and long-chain fat primary amine rub
You are than being 1:3.
In aziridine ring-opening reaction, the acidic catalyst is the phosphate aqueous solution that mass fraction is 85%, is used
Amount is the 1% of total mass of raw material.
Replace in carboxyl in quaternary ammonium reaction, weak basic condition pH=9~10, reaction solution is adjusted to alkalescent with NaOH.
Replace in carboxyl in quaternary ammonium reaction, the amount of the substance of sodium chloroacetate is (the 3- ethylene imine of trimethylolpropane-three
Base propionic ester) 6 times.
The invention has the following advantages that
(1) present invention introduces a large amount of carboxylic acid ions on dispersant molecule chain, on the one hand, carboxylate group has fine
Water solubility, the combination of molecule and graphene can be enable fully dispersed in water；On the other hand, sulfonate ion increases
Repulsive interaction between Zeta potential and nanoparticle.
(2) present invention introduces quaternary ammonium salt cationic on dispersant molecule chain, increases the aquation of star-like amphoteric dispersant
Ability and thermal stability.
(3) dispersant molecule structure of the invention is hub-and-spoke configuration, increases the steric restriction effect between graphene particle.
Therefore star-like amphoteric dispersant dispersion effect of the invention is more efficient, and dispersion stabilization is good.
Specific embodiment
The present invention adopts the following technical scheme:
A kind of star-like dispersing agent of both sexes for dispersing nanoparticles, the structural formula of the surfactant are as follows:
Wherein, R1It is long aliphatic chain, carbon atom number is 12~18 in carbochain.
The method for preparing a kind of star-like dispersing agent of above-mentioned both sexes for dispersing nanoparticles, steps of the method are:
Trimethylolpropane-three is added dropwise in the reaction flask equipped with long-chain fat primary amine ethanol solution and acidic catalyst
(3- aziridinyl propionic ester) reaction solution carries out first step aziridine ring-opening reaction, wherein (the 3- aziridinyl of hydroxymethyl-propane-three
Propionic ester) and long-chain fat primary amine molar ratio be 1:3, in 50~70 DEG C of 6~8h of reaction；Again by above-mentioned reaction solution NaOH tune
To alkalescent (pH=9~10), sodium chloroacetate aqueous solution is added dropwise and carries out the substitution of second step carboxyl and quaternary ammonium reaction, wherein chloroethene
The amount of the substance of sour sodium is 6 times of trimethylolpropane-three (3- aziridinyl propionic ester), 70~90 DEG C of 10~16h of reaction.Instead
Insoluble matter is removed after answering, concentration of reaction solution is isolated and purified with product with toluene column chromatography, is dried under vacuum to constant weight just
Obtain product.It is as follows to synthesize equation:
Wherein, R1It is long aliphatic chain, carbon atom number is 12~18 in carbochain.
Below by the technical scheme in the embodiment of the invention is clearly and completely described.Obviously, described implementation
Example is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, the common skill in this field
Art personnel every other embodiment obtained without creative efforts belongs to the model that the present invention protects
It encloses.
Embodiment 1
(1) in the dodecyl primary amine ethanol solution (34.69g, wherein containing dodecyl primary for being 80% equipped with mass fraction
Amine 27.75g, 0.15mol) and acidic catalyst (85%H3PO4, 0.50g), 50 DEG C are warming up to, it is 70% that mass fraction, which is added dropwise,
Trimethylolpropane-three (3- aziridinyl propionic ester) ethanol solution (35.42g, wherein (the 3- a word used for translation third containing trimethylolpropane-three
Piperidinyl propionic ester) 21.25g, 0.05mol), time for adding 40min.After being added dropwise, it is warming up to 70 DEG C of reaction 6h.
(2) above-mentioned reaction solution is adjusted to alkalescent (pH=9~10) with NaOH, the monoxone that mass fraction is 80% is added dropwise
Sodium water solution (43.68g, wherein 34.94g containing sodium chloroacetate, 0.30mol), time for adding 60min, in 70 DEG C of reaction 16h；
Insoluble matter is removed after reaction, and concentration of reaction solution is isolated and purified with product with toluene column chromatography, is dried under vacuum to constant weight
Obtain product.
The structural formula of 1 products therefrom of embodiment are as follows:
1H NMR (300MHz, DMSO): δ 4.35 (s, 24H), 3.94 (s, 6H), 3.63~3.68 (m, 18H), 3.22 (s,
6H), 2.69 (t, 6H), 1.69~1.71 (m, 8H), 1.26~1.29 (s, 54H), 0.83~0.88 (m, 12H) ppm.
13C NMR (300MHz, DMSO): δ 175.4,173.1,65.9~66.4,58.8,56.2,53.2~53.5,
35.7,31.9,29.3~29.6,26.8,22.7,14.1,7.0ppm.
Dispersion performance test:
Using commercially available nano zine oxide, preparation of nano zinc oxide suspension.Clean reagent bottle is chosen, weighs difference respectively
The dispersing agent and 25mg nano zine oxide of the preparation of 5mg embodiment 1 are weighed, water 10mL is added, is stirred under the revolving speed of 3000r/min
15min, then the ultrasound 10min under the power of 100W, and the dispersion liquid is poured into 10mL rub oral examination tube, obtain nano zine oxide
Dispersion liquid.And do blank test.
The test of dispersion particle diameter distribution: it takes in above-mentioned nano zinc oxide fluid dispersion on laser granularity distribution tester
Particle diameter distribution is tested, average grain diameter 95nm illustrates that dispersion effect is good.Under similarity condition, the average grain diameter of blank sample is
346nm。
Delamination and settling height to above-mentioned nano zinc oxide fluid dispersion carry out apparent observation in different time periods,
Complete to start timing since stirring, observed for the third time after second observation, 4h after observation, 2h after 30min for the first time and 8h after the 4th
Secondary observation.By observation in different time periods it can be seen that above-mentioned nano zinc oxide fluid dispersion is equal after 30min, 2h and 4h
Do not occur sedimentation phenomenon, slight sedimentation phenomenon occurs in hour after 8h, and settling height is than 4.1%.And blank sample is stood less than 30min
There have been serious sedimentation phenomenons, and settling height is than 47.6%.
Embodiment 2
(1) in the octadecyl primary amine ethanol solution (50.53g, wherein containing octadecyl primary for being 80% equipped with mass fraction
Amine 40.43g, 0.15mol) and acidic catalyst (85%H3PO4, 0.60g), 50 DEG C are warming up to, it is 70% that mass fraction, which is added dropwise,
Trimethylolpropane-three (3- aziridinyl propionic ester) ethanol solution (35.42g, wherein (the 3- a word used for translation third containing trimethylolpropane-three
Piperidinyl propionic ester) 21.25g, 0.05mol), time for adding 40min.After being added dropwise, it is warming up to 50 DEG C of reaction 8h.
(2) above-mentioned reaction solution is adjusted to alkalescent (pH=9~10) with NaOH, the monoxone that mass fraction is 80% is added dropwise
Sodium water solution (43.68g, wherein 34.94g containing sodium chloroacetate, 0.30mol), time for adding 60min, in 90 DEG C of reaction 10h；
Insoluble matter is removed after reaction, and concentration of reaction solution is isolated and purified with product with toluene column chromatography, is dried under vacuum to constant weight
Obtain product.
The structural formula of 2 products therefrom of embodiment are as follows:
1H NMR (300MHz, DMSO): δ 4.35 (s, 24H), 3.94 (s, 6H), 3.63~3.68 (m, 18H), 3.22 (s,
6H), 2.69 (t, 6H), 1.69~1.71 (m, 8H), 1.26~1.29 (s, 90H), 0.83~0.88 (m, 12H) ppm.
13C NMR (300MHz, DMSO): δ 175.4,173.1,65.9~66.4,58.8,56.2,53.2~53.5,
35.7,31.9,29.3~29.6,26.8,22.7,14.1,7.0ppm.
Dispersion performance test:
Using commercially available nano aluminium oxide, preparation of nano aluminum oxide suspension.Clean reagent bottle is chosen, weighs difference respectively
The dispersing agent and 25mg nano aluminium oxide of the preparation of 5mg embodiment 2 are weighed, water 10mL is added, is stirred under the revolving speed of 3000r/min
15min, then the ultrasound 10min under the power of 100W, and the dispersion liquid is poured into 10mL rub oral examination tube, obtain nano aluminium oxide
Dispersion liquid.And do blank test.
The test of dispersion particle diameter distribution: it takes in above-mentioned nano aluminium oxide dispersion liquid on laser granularity distribution tester
Particle diameter distribution is tested, average grain diameter 93nm illustrates that dispersion effect is good.Under similarity condition, the average grain diameter of blank sample is
375nm。
Delamination and settling height to above-mentioned nano aluminium oxide dispersion liquid carry out apparent observation in different time periods,
Complete to start timing since stirring, observed for the third time after second observation, 4h after observation, 2h after 30min for the first time and 8h after the 4th
Secondary observation.By observation in different time periods it can be seen that above-mentioned nano aluminium oxide dispersion liquid is equal after 30min, 2h and 4h
Do not occur sedimentation phenomenon, slight sedimentation phenomenon occurs in hour after 8h, and settling height is than 4.8%.And blank sample is stood less than 30min
There have been serious sedimentation phenomenons, and settling height is than 53.0%.
Embodiment 3
(1) in the myristyl primary amine ethanol solution (40.03g, wherein containing myristyl primary for being 80% equipped with mass fraction
Amine 32.03g, 0.15mol) and acidic catalyst (85%H3PO4, 0.50g), 50 DEG C are warming up to, it is 70% that mass fraction, which is added dropwise,
Trimethylolpropane-three (3- aziridinyl propionic ester) ethanol solution (35.42g, wherein (the 3- a word used for translation third containing trimethylolpropane-three
Piperidinyl propionic ester) 21.25g, 0.05mol), time for adding 40min.After being added dropwise, it is warming up to 60 DEG C of reaction 7h.
(2) above-mentioned reaction solution is adjusted to alkalescent (pH=9~10) with NaOH, the monoxone that mass fraction is 80% is added dropwise
Sodium water solution (43.68g, wherein 34.94g containing sodium chloroacetate, 0.30mol), time for adding 60min, in 80 DEG C of reaction 14h；
Insoluble matter is removed after reaction, and concentration of reaction solution is isolated and purified with product with toluene column chromatography, is dried under vacuum to constant weight
Obtain product.
The structural formula of 3 products therefrom of embodiment are as follows:
Dispersion performance test:
Using commercially available nano silica, preparation of nano silica suspension.Clean reagent bottle is chosen, is weighed respectively
The dispersing agent and 25mg nano silica for weighing the preparation of 5mg embodiment 3 respectively, are added water 10mL, in the revolving speed of 3000r/min
Lower stirring 15min, then the ultrasound 10min under the power of 100W, and the dispersion liquid is poured into 10mL rub oral examination tube, obtain nanometer
Silica dispersions.And do blank test.
The test of dispersion particle diameter distribution: it takes in above-mentioned nano silicon dioxide dispersion in laser granularity distribution tester
Upper test particle diameter distribution, average grain diameter 72nm illustrate that dispersion effect is good.Under similarity condition, the average grain diameter of blank sample is
335nm。
Delamination and settling height to above-mentioned nano silicon dioxide dispersion carry out apparent sight in different time periods
Examine, complete to start timing since stirring, observed for the third time after second observation, 4h after observation, 2h after 30min for the first time and 8h after the
Four observations.By observation in different time periods it can be seen that above-mentioned nano silicon dioxide dispersion is in 30min, 2h and 4h
Do not occur sedimentation phenomenon afterwards, slight sedimentation phenomenon occurs in hour after 8h, and settling height is than 8.4%.And blank sample stand less than
30min is there have been serious sedimentation phenomenon, and settling height is than 70.5%.
Embodiment 4
(1) in the cetyl primary amine ethanol solution (45.29g, wherein containing cetyl primary for being 80% equipped with mass fraction
Amine 36.23g, 0.15mol) and acidic catalyst (85%H3PO4, 0.50g), 50 DEG C are warming up to, it is 70% that mass fraction, which is added dropwise,
Trimethylolpropane-three (3- aziridinyl propionic ester) ethanol solution (35.42g, wherein (the 3- a word used for translation third containing trimethylolpropane-three
Piperidinyl propionic ester) 21.25g, 0.05mol), time for adding 40min.After being added dropwise, it is warming up to 60 DEG C of reaction 7h.
(2) above-mentioned reaction solution is adjusted to alkalescent (pH=9~10) with NaOH, the monoxone that mass fraction is 80% is added dropwise
Sodium water solution (43.68g, wherein 34.94g containing sodium chloroacetate, 0.30mol), time for adding 60min, in 80 DEG C of reaction 12h；
Insoluble matter is removed after reaction, and concentration of reaction solution is isolated and purified with product with toluene column chromatography, is dried under vacuum to constant weight
Obtain product.
The structural formula of 4 products therefrom of embodiment are as follows:
Dispersion performance test:
Using commercially available nano calcium oxide, preparation of nano calcium oxide suspension.Clean reagent bottle is chosen, weighs difference respectively
The dispersing agent and 25mg nano calcium oxide of the preparation of 5mg embodiment 3 are weighed, water 10mL is added, is stirred under the revolving speed of 3000r/min
15min, then the ultrasound 10min under the power of 100W, and the dispersion liquid is poured into 10mL rub oral examination tube, obtain nano calcium oxide
Dispersion liquid.And do blank test.
The test of dispersion particle diameter distribution: it takes in above-mentioned nano calcium oxide dispersion liquid on laser granularity distribution tester
Particle diameter distribution is tested, average grain diameter 80nm illustrates that dispersion effect is good.Under similarity condition, the average grain diameter of blank sample is
385nm。
Delamination and settling height to above-mentioned nano calcium oxide dispersion liquid carry out apparent observation in different time periods,
Complete to start timing since stirring, observed for the third time after second observation, 4h after observation, 2h after 30min for the first time and 8h after the 4th
Secondary observation.By observation in different time periods it can be seen that above-mentioned nano calcium oxide dispersion liquid is equal after 30min, 2h and 4h
Do not occur sedimentation phenomenon, slight sedimentation phenomenon occurs in hour after 8h, and settling height is than 3.0%.And blank sample is stood less than 30min
There have been serious sedimentation phenomenons, and settling height is than 63.5%.
The above content is further detailed description of the invention, and it cannot be said that a specific embodiment of the invention only
It is limited to this, for those of ordinary skill in the art to which the present invention belongs, without departing from the inventive concept of the premise, also
Several simple deduction or replace can be made, the present invention is all shall be regarded as belonging to by the claims submitted and determines protection
Range.
Claims (7)
1. a kind of application of star-like carboxylic acid group's zwitterionic surfactant as dispersing agent, which is characterized in that be applied to nanometer
In the dispersion of particle, the structural formula of compound are as follows:
Wherein, R1It is long aliphatic chain, carbon atom number is 12~18 in carbochain；
The preparation method of star-like carboxylic acid group's zwitterionic surfactant the following steps are included:
Trimethylolpropane-three (3- aziridinyl propionic ester) is added into long-chain fat primary amine ethanol solution and acidic catalyst
Reaction solution carries out aziridine ring-opening reaction, in 50~80 DEG C of 6~8h of reaction；
Sodium chloroacetate aqueous solution is added under weak basic condition, in Xiang Shangshu reactant and carries out carboxyl substitution and quaternary ammonium reaction,
In 70~90 DEG C of 10~16h of reaction；Remove insoluble matter after reaction, concentration of reaction solution is purified point with toluene column chromatography
Product is separated out, constant weight is dried under vacuum to and just obtains product.
2. a kind of application of the star-like carboxylic acid group's zwitterionic surfactant according to claim 1 as dispersing agent,
It is characterized in that, the mass ratio of dispersing agent and nano particle is 5:25.
3. a kind of application of the star-like carboxylic acid group's zwitterionic surfactant according to claim 1 as dispersing agent, institute
Stating nano particle is nano silica, nanometer calcium carbonate, nano zine oxide and nano aluminium oxide.
4. a kind of application of the star-like carboxylic acid group's zwitterionic surfactant according to claim 1 as dispersing agent,
It is characterized in that, in aziridine ring-opening reaction, trimethylolpropane-three (3- aziridinyl propionic ester) and long-chain fat primary amine rub
You are than being 1:3.
5. a kind of application of the star-like carboxylic acid group's zwitterionic surfactant according to claim 1 as dispersing agent,
It is characterized in that, in aziridine ring-opening reaction, the acidic catalyst is the phosphate aqueous solution that mass fraction is 85%, is used
Amount is the 1% of total mass of raw material.
6. a kind of application of the star-like carboxylic acid group's zwitterionic surfactant according to claim 1 as dispersing agent,
It is characterized in that, replaces in carboxyl in quaternary ammonium reaction, weak basic condition pH=9~10, reaction solution is adjusted to alkalescent with NaOH.
7. a kind of application of the star-like carboxylic acid group's zwitterionic surfactant according to claim 1 as dispersing agent,
It is characterized in that, replaces in carboxyl in quaternary ammonium reaction, the amount of the substance of sodium chloroacetate is (the 3- a word used for translation third of trimethylolpropane-three
Piperidinyl propionic ester) 6 times.
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| CN114664497A (en) * | 2022-04-14 | 2022-06-24 | 北京化工大学 | Modified silver nanowire dispersion liquid, preparation method thereof and preparation method of transparent conductive electrode |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999035120A1 (en) * | 1998-01-09 | 1999-07-15 | Witco Corporation | Novel quaternary ammonium compounds, compositions containing them, and uses thereof |
| CN101450295A (en) * | 2008-12-15 | 2009-06-10 | 南京金杉汽车工程塑料有限责任公司 | Efficient zwitterionic gemini surfactant and synthesis method thereof |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999035120A1 (en) * | 1998-01-09 | 1999-07-15 | Witco Corporation | Novel quaternary ammonium compounds, compositions containing them, and uses thereof |
| CN101450295A (en) * | 2008-12-15 | 2009-06-10 | 南京金杉汽车工程塑料有限责任公司 | Efficient zwitterionic gemini surfactant and synthesis method thereof |
Non-Patent Citations (1)
| Title |
|---|
| 两亲性超支化聚(酯-胺)的溶液聚集行为;唐黎明等;《高分子材料科学与工程》;20060930;第22卷(第5期);前言、第2节 * |
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