CN108892786B - Lignin/surfactant composite nano particle and preparation method thereof - Google Patents
Lignin/surfactant composite nano particle and preparation method thereof Download PDFInfo
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Abstract
The invention belongs to the technical field of nano materials, and discloses lignin/surfactant composite nanoparticles with good dispersion in water and a preparation method thereof. The method comprises the following steps: (1) dispersing 100 parts by mass of lignin in alkali liquor, adjusting the pH of the system to 9-12, adding 10-25 parts by mass of epoxy chloropropane, and carrying out crosslinking reaction at 80-95 ℃ for 1-3 h to obtain high molecular weight lignin; (2) adding high molecular weight lignin, alkali and a surfactant into water to obtain a mixed solution with the pH of 9-12; (3) and adding acid into the mixed solution until the pH value of the solution is 4-6, and stirring to obtain the aqueous dispersion of the lignin/surfactant composite nanoparticles. The lignin/surfactant composite nanoparticles with excellent water dispersibility, which are prepared by the method, have the hydrodynamic radius of 40-500 nm, can be stably dispersed in water, and are easy to mix with other components.
Description
Technical Field
The invention belongs to the technical field of nano materials, and particularly relates to a lignin/surfactant composite nanoparticle with good dispersion in water and a preparation method thereof.
Background
Nanoparticles are very valuable materials, and most of the nanoparticles are prepared from inorganic materials, and the inorganic nanoparticles, especially those made of metal or mineral materials, can exist in the environment stably for a long time, and cause continuous damage to the environment. Moreover, since most inorganic materials do not have biocompatibility and biodegradability, which limits their applications in many fields, only a few inorganic nanoparticles can be applied to the fields of food, medicine, and cosmetics. The biomass material has the advantages that the traditional inorganic material does not have, such as reproducibility, biocompatibility, biodegradability and the like.
Lignin is the second most abundant natural polymer chemical after cellulose and is also the most abundant renewable aromatic substance. Nearly 7000 million tons of industrial lignin are produced worldwide each year, 90% of which are treated in a combustion manner, and only 10% are applied to high-valued products. The water insolubility of lignin is a major factor limiting its industrial processing and large-scale application. The method improves the dispersion performance of lignin in water, and the preparation of the water-dispersible lignin nanoparticles is an important way for improving the application value of the lignin. Water-dispersible lignin nanoparticles hold promise for applications such as biomass-based binders, stabilizers, additives, and the like. There are reports of lignin nanoparticles for enhancing the strength of phenolic resin foams (Composites Science and Technology,2012,72: 667-. In addition, the application of water-dispersed polymer nanoparticles in drug delivery systems has also been extensively studied (Nature,1998,392:5-10), which may also be a potential application of lignin nanoparticles. The lignin well dispersed in water can be conveniently mixed with other components, and is beneficial to developing more process technologies for utilizing the lignin.
The current methods for preparing water-dispersible lignin nanoparticles can be largely classified into solvent methods and physical methods. The solvent method is that some strong polar organic solvents such as ethylene glycol, tetrahydrofuran, dimethyl sulfoxide and the like are used for dissolving lignin and then slowly introducing the dissolved lignin into poor solvent of the lignin, namely water, so that the good solvent of the lignin is diluted and the dissolved lignin is separated out into nano-scale particles. The use of a large amount of organic solvent in the solvent method easily brings potential environmental hazards, and the application of the prepared lignin nanoparticles is also limited due to the residue of harmful organic solvent. The physical methods for preparing the lignin nanoparticles mainly comprise a high-pressure shearing method, a spray drying method, an ultrasonic method and the like, compared with a solvent method, the dependence on chemical reagents can be reduced to a great extent, the prepared lignin particles have the advantage of low toxicity, but the methods generally have the defects of strict operating conditions and high energy consumption, and the prepared lignin nanoparticles are easy to agglomerate and have poor water dispersion performance.
In view of the above, there is a need to develop a method for preparing water-dispersible lignin nanoparticles under mild operating conditions.
Disclosure of Invention
In order to overcome the disadvantages and shortcomings of the prior art, the primary object of the present invention is to provide a method for preparing lignin/surfactant composite nanoparticles with good dispersion in water.
In alkaline solution, phenolic hydroxyl and alcoholic hydroxyl of lignin are ionized to generate electrostatic repulsive force to expand and dissolve the lignin molecular skeleton. And then acid is added to change the pH value of the solution so as to protonate phenolic hydroxyl groups, carboxyl groups and the like of the lignin and shrink molecular frameworks, thereby clamping the surfactant molecules to form the composite particles. The hydrophilic group of the surfactant endows lignin particles with more negative charges, so that strong electrostatic repulsion action is generated among the lignin particles, and the lignin/surfactant composite nanoparticles are stably dispersed in water.
The invention also aims to provide the lignin/surfactant composite nanoparticles which are well dispersed in water and prepared by the method. The composite nano particle is a composite of lignin and a surfactant.
The purpose of the invention is realized by the following scheme:
a preparation method of lignin/surfactant composite nanoparticles well dispersed in water comprises the following steps:
(1) dispersing 100 parts by mass of lignin in alkali liquor, adjusting the pH of the system to 9-12, adding 10-25 parts by mass of epoxy chloropropane, and carrying out crosslinking reaction at 80-95 ℃ for 1-3 h to obtain high molecular weight lignin;
(2) adding high molecular weight lignin, alkali and a surfactant into water to obtain a mixed solution with the pH of 9-12;
(3) and adding acid into the mixed solution until the pH value of the solution is 4-6, and stirring to obtain the aqueous dispersion of the lignin/surfactant composite nanoparticles.
In the step (1), the alkali liquor can be sodium hydroxide solution, potassium hydroxide solution, ammonia water and the like.
In the step (1), the concentration of the lignin in the alkali liquor is preferably 20-40 wt%, and more preferably 30 wt%.
In step (1), the pH is preferably 10.
In the step (1), the reacted system can be dried by rotary evaporation to obtain the high molecular weight lignin.
In the step (2), the concentration of the lignin in the mixed solution is preferably 0.1-5 wt%.
In the step (2), the concentration of the surfactant in the mixed solution is preferably 0.01-2 wt%.
In the step (2), the surfactant is at least one of sodium oleate, sodium dodecyl benzene sulfonate and hexadecyl trimethyl ammonium bromide.
In the step (2), the alkali is one of sodium hydroxide, potassium hydroxide and ammonia water.
In the step (3), the acid is one of hydrochloric acid, sulfuric acid and nitric acid.
In order to further and better achieve the object of the present invention, the lignin in step (1) is preferably one of alkali lignin and enzymatic hydrolysis lignin.
In order to further and better achieve the aim of the invention, the alkali lignin is acid-out lignin powder which is one of wood pulp black liquor, bamboo pulp black liquor, wheat straw pulp black liquor, reed pulp black liquor, bagasse pulp black liquor, asparagus pulp black liquor, cotton stalk pulp black liquor and cotton pulp black liquor and is subjected to acid-out drying; the enzymatic hydrolysis lignin is lignin separated and extracted from residues of alcohol prepared by fermenting cellulose in plant raw materials.
In order to further achieve the object of the present invention, in the step (3), the stirring is a continuous stirring.
In order to further and better achieve the object of the present invention, the lignin/surfactant composite nanoparticle dispersion obtained in step (3) may be dialyzed to remove impurities such as free surfactant, salt, etc., to obtain a purified lignin/surfactant composite nanoparticle dispersion.
The invention also provides the lignin/surfactant composite nanoparticles with excellent water dispersibility prepared by the method. The composite nanoparticle has a hydrodynamic radius of 40-500 nm, is a complex formed by lignin particles and surfactant molecules, a hydrophobic chain of the surfactant is combined with a hydrophobic inner core of the lignin particles, and a hydrophilic group is arranged outside the lignin particles. The hydrophilic group of the surfactant forms strong electrostatic repulsion between the lignin particles, so that the lignin particles can be dispersed in water very stably without agglomerating into large particles. The excellent water dispersion performance enables the lignin to be easily and fully mixed with other various components, which is beneficial to high-value utilization of the lignin in various systems.
Compared with the prior art, the invention has the following advantages and beneficial effects:
(1) according to the invention, the high molecular weight lignin is obtained by a crosslinking method, so that the hydrophobicity of the lignin is improved, the hydrophobic chain of the surfactant can be more firmly combined with the hydrophobic core of the lignin, the lignin particles can be separated out at a higher pH value, the composite nanoparticles can be prepared in an aqueous solution only by using two reagents, namely alkali and the surfactant without any organic reagent, the nanocrystallization condition is mild, the operation is simple, and various functional groups of the lignin are reserved.
(2) The lignin/surfactant composite nanoparticles prepared by the method have the hydraulic diameter of 40-500 nm, and the particle size can be easily regulated and controlled by regulating the dosage of the lignin and the surfactant. The electrostatic repulsion effect brought by the surfactant molecules enables the composite nanoparticles to have excellent water dispersion performance, and aggregation and settlement can not occur after long-term storage.
(3) The invention prepares the lignin with poor solubility into the nano-scale composite particles which can be stably dispersed, overcomes the defects that the lignin is difficult to dissolve and disperse in water, and provides an important treatment method for the subsequent high-value utilization of the lignin.
Drawings
FIG. 1 is a transmission electron micrograph of a lignin/surfactant composite nanoparticle.
Fig. 2 is a particle size distribution diagram of the lignin/surfactant composite nanoparticles.
Detailed Description
The present invention will be described in further detail with reference to examples, but the embodiments of the present invention are not limited thereto.
The materials referred to in the following examples are commercially available.
Example 1
(1) Preparing 100 parts by mass of acid-out lignin powder from wood pulp black liquor into an aqueous solution with the concentration of 20 wt% and the pH value of 12 by using sodium hydroxide, adding 15 parts by mass of epoxy chloropropane, carrying out crosslinking reaction for 2 hours at 95 ℃, and carrying out rotary evaporation and drying on the reaction solution to obtain the high-molecular-weight lignin.
(2) Adding 1 part by mass of the high molecular weight lignin into 100 parts by mass of water, adding a proper amount of sodium hydroxide to adjust the pH of the solution to 9 so as to completely dissolve the lignin, adding 0.4 part by mass of sodium dodecyl benzene sulfonate, and continuously stirring so as to completely dissolve the sodium dodecyl benzene sulfonate to obtain a mixed solution.
(3) And (3) dropwise adding hydrochloric acid into the mixed solution until the pH value of the solution is 4, and continuously stirring to obtain the dispersion liquid of the lignin/sodium dodecyl benzene sulfonate composite nanoparticles.
Example 2
(1) Preparing 100 parts by mass of enzymatic hydrolysis lignin into an aqueous solution with the concentration of 30 wt% and the pH value of 10 by using ammonia water, adding 20 parts by mass of epoxy chloropropane, carrying out crosslinking reaction for 2 hours at 90 ℃, and carrying out rotary evaporation and drying on the reaction solution to obtain the high molecular weight lignin.
(2) Adding 0.5 mass part of the high molecular weight lignin into 100 mass parts of water, adding a proper amount of ammonia water to adjust the pH value of the solution to 12 so as to completely dissolve the lignin, adding 0.5 mass part of sodium oleate and 0.5 mass part of sodium dodecyl benzene sulfonate, and continuously stirring so as to completely dissolve the sodium oleate and the sodium dodecyl benzene sulfonate to obtain a mixed solution.
(3) And dropwise adding sulfuric acid into the mixed solution until the pH value of the solution is 6, and continuously stirring to obtain the dispersion liquid of the lignin/sodium oleate-sodium dodecyl benzene sulfonate composite nanoparticles.
Example 3
(1) Preparing 100 parts by mass of acid-out lignin powder from the bamboo pulp black liquor into an aqueous solution with the concentration of 40 wt% and the pH value of 9 by using sodium hydroxide, adding 10 parts by mass of epoxy chloropropane, carrying out cross-linking reaction at 95 ℃ for 3 hours, and carrying out rotary evaporation and drying on the reaction solution to obtain the high-molecular-weight lignin.
(2) Adding 5 parts by mass of the high molecular weight lignin into 100 parts by mass of water, adding a proper amount of sodium hydroxide to adjust the pH of the solution to 11 so as to completely dissolve the lignin, adding 2 parts by mass of sodium oleate, and continuously stirring so as to completely dissolve the sodium oleate to obtain a mixed solution.
(3) And dropwise adding sulfuric acid into the mixed solution until the pH value of the solution is 5, and continuously stirring to obtain the lignin/sodium oleate composite nanoparticle dispersion liquid.
Example 4
(1) Preparing acid-out lignin powder from wheat straw pulp black liquor by 100 parts by mass into aqueous solution with the concentration of 35 wt% and the pH value of 11 by using potassium hydroxide, adding 10 parts by mass of epoxy chloropropane, carrying out cross-linking reaction for 3 hours at 90 ℃, and carrying out rotary evaporation on reaction liquid to obtain the high-molecular-weight lignin.
(2) Adding 2 parts by mass of the high molecular weight lignin into 100 parts by mass of water, adding a proper amount of potassium hydroxide to adjust the pH of the solution to 11.5 to completely dissolve the lignin, adding 0.6 part by mass of sodium dodecyl benzene sulfonate, and continuously stirring to completely dissolve the sodium dodecyl benzene sulfonate to obtain a mixed solution.
(3) And (3) dropwise adding nitric acid into the mixed solution until the pH value of the solution is 5, and continuously stirring to obtain the dispersion liquid of the lignin/sodium dodecyl benzene sulfonate composite nanoparticles.
Example 5
(1) Preparing 100 parts by mass of acid-out lignin powder from wood pulp black liquor into an aqueous solution with the concentration of 30 wt% and the pH value of 10 by using sodium hydroxide, adding 25 parts by mass of epoxy chloropropane, carrying out crosslinking reaction for 1h at 95 ℃, and carrying out rotary evaporation on the reaction solution to obtain the crosslinked lignin.
(2) Adding 0.1 part by mass of the high molecular weight lignin into 100 parts by mass of water, adding a proper amount of sodium hydroxide to adjust the pH of the solution to 12.8 so as to completely dissolve the lignin, adding 0.01 part by mass of hexadecyl trimethyl ammonium bromide, and continuously stirring so as to completely dissolve the hexadecyl trimethyl ammonium bromide to obtain a mixed solution.
(3) And (3) dropwise adding hydrochloric acid into the mixed solution until the pH value of the solution is 4, and continuously stirring to obtain the dispersion liquid of the lignin/hexadecyl trimethyl ammonium bromide composite nanoparticles.
Description of the effects of the examples:
the effects will be described by taking example 1 as an example.
FIG. 1 is a transmission electron micrograph of the product of example 1 taken by transmission electron microscopy. It can be seen that the nanoparticles are in the form of irregular fragments with a particle size of about 40 nm. FIG. 2 is a particle size distribution diagram of the product of example 1 measured by a dynamic light scattering instrument, and the result shows that the average hydraulic diameter of the nanoparticle is only 70nm, which illustrates that the lignin/surfactant composite nanoparticle can be prepared by the method. The slight difference in particle size data is due to the difference in the measurement methods of the two instruments.
Table 1 shows the sulfur content of the product of example 1 and the raw alkali lignin after dialysis to remove free sodium dodecylbenzene sulfonate, from which it can be seen that the sulfur content of the product of this example is significantly higher than that of the raw alkali lignin, which indicates that sodium dodecylbenzene sulfonate is successfully and firmly compounded with lignin to form nanoparticles.
TABLE 1 Sulfur content of Lignin feedstock versus nanoparticles of example 1
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (9)
1. A preparation method of lignin/surfactant composite nanoparticles is characterized by comprising the following steps:
(1) dispersing 100 parts by mass of lignin in alkali liquor, adjusting the pH of the system to 9-12, adding 10-25 parts by mass of epoxy chloropropane, and carrying out crosslinking reaction at 80-95 ℃ for 1-3 h to obtain high molecular weight lignin;
(2) adding high molecular weight lignin, alkali and a surfactant into water to obtain a mixed solution with the pH of 9-12;
(3) adding acid into the mixed solution until the pH value of the solution is 4-6, and stirring to obtain aqueous dispersion of the lignin/surfactant composite nanoparticles;
in the step (2), the surfactant is at least one of sodium oleate, sodium dodecyl benzene sulfonate and hexadecyl trimethyl ammonium bromide.
2. The method for preparing lignin/surfactant composite nanoparticles according to claim 1, wherein: in the step (1), the alkali liquor is sodium hydroxide solution, potassium hydroxide solution or ammonia water.
3. The method for preparing lignin/surfactant composite nanoparticles according to claim 1, wherein: in the step (1), the concentration of the lignin in the alkali liquor is 20-40 wt%.
4. The method for preparing lignin/surfactant composite nanoparticles according to claim 1, wherein: in the step (1), the pH is 10.
5. The method for preparing lignin/surfactant composite nanoparticles according to claim 1, wherein: in the step (2), the concentration of the lignin in the mixed solution is 0.1-5 wt%.
6. The method for preparing lignin/surfactant composite nanoparticles according to claim 1, wherein: in the step (2), the concentration of the surfactant in the mixed solution is 0.01-2 wt%.
7. The method for preparing lignin/surfactant composite nanoparticles according to claim 1, wherein: the lignin in the step (1) is at least one of alkali lignin and enzymatic hydrolysis lignin; in the step (2), the alkali is at least one of sodium hydroxide, potassium hydroxide and ammonia water; in the step (3), the acid is at least one of hydrochloric acid, sulfuric acid and nitric acid.
8. The method for preparing lignin/surfactant composite nanoparticles according to claim 7, wherein: the alkali lignin is acid-out lignin powder which is prepared by acid-out drying one of wood pulp black liquor, bamboo pulp black liquor, wheat straw pulp black liquor, reed pulp black liquor, bagasse pulp black liquor, asparagus pulp black liquor, cotton stalk pulp black liquor and cotton pulp black liquor; the enzymatic hydrolysis lignin is lignin separated and extracted from residues of alcohol prepared by fermenting cellulose in plant raw materials.
9. A lignin/surfactant composite nanoparticle, characterized by being obtained by the preparation method according to any one of claims 1 to 8.
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| CN109627466A (en) * | 2018-12-12 | 2019-04-16 | 天津科技大学 | A kind of preparation method of lignin nano spherical particle |
| CN113651963B (en) * | 2021-07-16 | 2022-05-24 | 华南理工大学 | Hyperbranched lignin-based cationic starch multifunctional composite flocculant and preparation and application thereof |
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| CN104147977A (en) * | 2014-07-09 | 2014-11-19 | 华南理工大学 | Lignin-based anion-cation type high-molecular surface active agent and preparation method thereof |
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