CN103254452A - Preparation method of lignin nanoparticle - Google Patents
Preparation method of lignin nanoparticle Download PDFInfo
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- CN103254452A CN103254452A CN2013101927871A CN201310192787A CN103254452A CN 103254452 A CN103254452 A CN 103254452A CN 2013101927871 A CN2013101927871 A CN 2013101927871A CN 201310192787 A CN201310192787 A CN 201310192787A CN 103254452 A CN103254452 A CN 103254452A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L97/00—Compositions of lignin-containing materials
- C08L97/005—Lignin
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H6/00—Macromolecular compounds derived from lignin, e.g. tannins, humic acids
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Abstract
The invention discloses a preparation method of a lignin nanoparticle and belongs to the chemical field of nanometer materials. The preparation method comprises the following steps of: dissolving a lignin raw material through an organic solvent; removing impurities; dropwise adding a proper amount of inorganic acid into filtrate to form lignin colloid; adding a cross-linking agent to perform cross-linking reaction with the lignin colloid; and adding water and stirring to dialyze to form lots of lignin nanoparticles of which the particle size is between 20nm to 200nm. The prepared lignin nanoparticle is excellent in dispersing performance and absorbing performance, and is expected to be applied to dispersing agents for wastewater treatment, dye, pesticide, water-coal-slurry systems and the like. The preparation method, disclosed by the invention, is simple and feasible; all the adopted solutions can be recovered, no adverse impacts are brought to the environment, and good application prospect is provided.
Description
Technical field
The present invention relates to the nano material chemical field, particularly a kind of preparation method of xylogen nano particle.
Background technology
Xylogen is the main component that constitutes the plant materials skeleton with Mierocrystalline cellulose, hemicellulose, and it mainly acts on is that Mierocrystalline cellulose is bonded together, for plant-growth provides support.The storage capacity of xylogen is only second to Mierocrystalline cellulose, is second biomass resource that enriches on the earth.The structure of xylogen is very complicated, is a kind of three-dimensional, amorphous high molecular polymer, and existing phenyl ring has carbochain again in its molecule, contains hydroxyl, aldehyde radical, ketone group, carboxyl etc. on the carbochain usually, also contains hydroxyl and a large amount of methoxyl groups on the phenyl ring.Industrial xylogen enters environment mainly as the by product of paper-making pulping industry and wood saccharification industry, as if recycling in addition not, will pollute environment.Therefore, no matter from the utilization of resources, still from environment protection, the research of xylogen and utilization all have been subjected to the attention of domestic and international researcher.
A large amount of research is carried out to xylogen in developed country in the world such as the U.S., Japan, Europe etc., particularly the U.S. in exploitation, utilize and accumulated rich experience aspect the xylogen.China recent years also increasing unit and researcher enters into the research and utilization ranks of xylogen, but also shoulders heavy responsibilities for the high added value development and use research of xylogen.
Nano material is the transitional region that is in cluster and macro object boundary, has significant surface effects, small-size effect and macro quanta tunnel effect.After material is made into nano particle, it will demonstrate many unusual characteristics, will take place significantly to change as its character of optics, calorifics, electricity, magnetics, mechanics and chemical aspect.As the minimizing along with size of particles, surface atom occupies ratio and increases sharply, but surface particle lacks the coordination of neighbour's atom, extremely unstable, be easy to be combined with other atom, show very high activity, so the specific surface area of the nano material of making is big, the surfactivity height can be widely used as various materials.Therefore; nano material is as a kind of emerge science technology that has the market application potential most; have a good application prospect at many industrial circles, as nano magnetic material, nano ceramic material, nano-sensor, functional materials, semiconductor material, nano catalytic material, environment protection industry, textile industry, mechanical industry etc.Though the existing long history of the research of xylogen at present mainly as low value-added product application, can be used for various field of fine chemical as industrial lignin is carried out suitable modification, as pesticide dispersing agent, slurries additive agent, water reducer and dye dispersant etc.Yet it utilizes scale but very limited, and up to the present, the recycling of the industrial lignin above 95% still rests on directly burning after concentrating, and causes the great wasting of resources.Therefore, xylogen is prepared into nano particle, will significantly increases it and use added value, be conducive to the utilization of environment protection and biomass resource simultaneously, meet the target of sustainable development, have positive environment and social effect.
In recent years, report about the xylogen nano particle is existing, provide a kind of overcritical method of producing the xylogen nano particle as Chinese patent CN102002165A: black liquid obtains paper industry rugose wood element through the acid out precipitation, paper industry rugose wood element is again through twice alkali dissolution Acid precipitation, employed alkali lye and acid solution are respectively sodium hydroxide solution and hydrochloric acid soln, obtain the highly industry xylogen, refining paper industry xylogen is through after the cryodrying, dissolve with dioxane, the insoluble lignin recovery of centrifugation is reused, obtain the xylogen dioxane solution, use CO 2 supercritical equipment, adopt the super-critical anti-solvent legal system to be equipped with the nanometer xylogen.This method is taked expensive overcritical equipment, and complex treatment process, therefore is difficult to apply.[Kilpelainen I Ilkka such as Kilpelainen, Xie H Haibo, King A Alistair, et al. Dissolution of Wood in Ionic Liquids. Journal of Agricultural and Food Chemistry, 2007,55 (22): 9142-9148.] use 1-butyl-3-methyl chloride (BmimCl) the ionic liquid dissolving timber with good solubility property, successfully obtain nano level xylogen particle.Be the effectively auto-polymerization effect of xylogen self phenolic hydroxyl group in the shielding processing process of solvent with the ionic liquid, but ionic liquid is expensive, and is difficult for obtaining, therefore make the application of nanometer xylogen be difficult to promote.
Summary of the invention
The object of the present invention is to provide a kind of preparation method of xylogen nano particle.The preparation technology of this method is simple, and production cost is low, has effectively improved the added value of product of xylogen, is conducive to applying of this technology.
The present invention is achieved through the following technical solutions:
A kind of preparation method of xylogen nano particle carries out pre-treatment with the xylogen raw material earlier, removes the insolubles in the raw material, obtains raw material filtrate; In raw material filtrate, add mineral acid and be prepared into xylogen colloidal sol; Be 100: 1 ~ 2 to add linking agents according to xylogen colloidal sol and linking agent weight ratio at last, carried out crosslinking reaction 1 ~ 2 hour, with cross-linking agent separate out, drying obtains the xylogen nano particle; Described linking agent is by one or more mixing in the following material: acetaldehyde, propionic aldehyde, butyraldehyde, glutaraldehyde, hexanedial.
The concrete grammar of described xylogen raw materials pretreatment is: the xylogen raw material is dissolved in the organic solvent, the weight ratio of xylogen raw material and organic solvent is: 1: 18 ~ 20, be heated to 30 ~ 50 ℃ then, stir and xylogen was fully dissolved in 1 ~ 3 hour, remove by filter the insolubles in the raw material, obtain filtrate; Described xylogen raw material comprises alkali lignin and ethanol xylogen.
Described organic solvent comprises one or more mixing in methylene dichloride, ethylene glycol, propylene glycol, the glycerol.
The preparation of described xylogen colloidal sol: dropping inorganic acid and keeps stirring to pH=2 ~ 2.5 in the raw material filtrate, obtains the xylogen colloid, and described mineral acid comprises one or more mixing in sulfuric acid, hydrochloric acid, the phosphoric acid.
The temperature of crosslinking reaction of the present invention is 30 ~ 50 ℃, crosslinking reaction is cooled to room temperature after finishing, in the crosslinking reaction system, drip water, the continuous dialysis of cross-linking agent is come out, again with washing, can get the xylogen nano-particle material in 12 ~ 18 hours in 60 ~ 80 ℃ of following vacuum-dryings, the xylogen nano particle diameter is 20 ~ 200nm.
Xylogen nano-particle material of the present invention can be applicable to the aspects such as dispersion agent of systems such as wastewater treatment and dyestuff, agricultural chemicals, coal water slurry.
The used xylogen source of the present invention comprises softwood, pourous wood and draft class plant, comprises dragon spruce, Pinus massoniana Lamb, tamarack, birch, Eucalyptus, poplar, wheat straw, straw, maize straw, bagasse, reed etc.Its separation means comprises the ethanol cooking process, alkaline cooking, and the xylogen of acquisition is respectively ethanol xylogen and alkali lignin.The xylogen of above-mentioned different material, different separation means gained can be bought from market, also can prepare voluntarily according to disclosed document.
The present invention has the following advantages:
(1) usually the source is extensive for raw material wood of the present invention, comprises softwood, pourous wood and draft class plant, comprises dragon spruce, Pinus massoniana Lamb, tamarack, birch, Eucalyptus, poplar, and wheat straw, straw, maize straw, bagasse, reed etc. are easy to obtain.
(2) organic solvent of the suitable environmental protection of the present invention prepares the xylogen nano particle, and as the dialysis agent, reagent is all recyclable, and is pollution-free with water, and the product no solvent residue is for potential market has been opened in the high value utilization of xylogen.
(3) Zhi Bei nano level xylogen particle has nanometer size effect, and every performance is greatly improved, and as dispersing property, absorption property, reactive behavior etc., has improved the potential range of application of xylogen greatly.
Description of drawings
Fig. 1 is the SEM figure of embodiment 1 gained nanometer xylogen particle;
Fig. 2 is the SEM figure of embodiment 2 gained nanometer xylogen particles;
Fig. 3 is the SEM figure of embodiment 3 gained nanometer xylogen particles;
Fig. 4 is the SEM figure of embodiment 4 gained nanometer xylogen particles;
Embodiment
The invention will be further described by reference to the accompanying drawings below by embodiment.
Embodiment 1
The preparation method of xylogen nano particle of the present invention comprises the steps:
(1) pre-treatment of xylogen raw material: the ethanol xylogen of getting 10 parts of quality is dissolved in 180 parts of glycerol organic solvents it, is heated to 30 ℃, stirs xylogen fully to be dissolved in 2 hours, removes by filter the insolubles in the raw material, obtains filtrate.
(2) preparation of xylogen colloidal sol: get 10 parts of quality above-mentioned steps (1) gained filtrate, to wherein dripping hydrochloric acid is to pH=2, maintenance is stirred, and obtains the xylogen colloid with certain speed.
(3) crosslinking reaction: get gained xylogen colloid in 50 parts of quality steps (2), heating in water bath to 40 ℃, to the glutaraldehyde that wherein drips 0.5 part of quality as linking agent, stirred 2 hours, xylogen colloid and glutaraldehyde generation crosslinking reaction, question response is cooled to room temperature after finishing, to wherein dripping water, the continuous dialysis of cross-linking agent is come out, wash with water again, can get the xylogen nano-particle material in 12 hours in 60 ℃ of following vacuum-dryings, as shown in Figure 1, the xylogen nano particle is irregularly shaped, and its particle size dispersion is more even, and particle diameter is in 50 ~ 200nm.
Embodiment 2
(1) pre-treatment of xylogen raw material: the alkali lignin of getting 15 parts of quality is dissolved in 270 parts of ethylene glycol and propylene glycol (60/40) organic solvent it, be heated to 50 ℃, stir and xylogen was fully dissolved in 1 hour, remove by filter the insolubles in the raw material, obtain filtrate.
(2) preparation of xylogen colloidal sol: get 30 parts of quality above-mentioned steps (1) gained filtrate,, keep stirring to wherein dripping sulfuric acid and hydrochloric acid to pH=2.5 with certain speed, obtain the xylogen colloid.
(3) crosslinking reaction: get gained xylogen colloid in 100 parts of quality steps (2), heating in water bath to 30 ℃, to the acetaldehyde that wherein drips 1 part of quality and butyraldehyde (1:1), stirred 1.5 hours, xylogen colloid and linking agent generation crosslinking reaction, question response is cooled to room temperature after finishing, to wherein dripping distilled water, the continuous dialysis of cross-linking agent is come out, use distilled water wash again, can get the xylogen nano-particle material in 18 hours in 80 ℃ of following vacuum-dryings, as shown in Figure 2, the xylogen nano particle is irregularly shaped, and its particle size dispersion is more even, and its grain diameter is in 20 ~ 200nm.
Embodiment 3
(1) pre-treatment of xylogen raw material: the alkali lignin of getting 20 parts of quality is dissolved in 400 parts of methylene dichloride and ethylene glycol (20/80) organic solvent it, be heated to 40 ℃, stir and xylogen was fully dissolved in 1 hour, remove by filter the insolubles in the raw material, obtain filtrate.
(2) preparation of xylogen colloidal sol: get 15 parts of quality above-mentioned steps (1) gained filtrate, to wherein dripping hydrochloric acid and phosphoric acid are to pH=2.2, maintenance is stirred, and obtains the xylogen colloid with certain speed.
(3) crosslinking reaction: get gained xylogen colloid in 50 parts of quality steps (2), heating in water bath to 40 ℃, to the butyraldehyde that wherein drips 0.5 part of quality and hexanedial (1:1) linking agent, stirred 1 hour, xylogen colloid and linking agent generation crosslinking reaction, question response is cooled to room temperature after finishing, to wherein dripping water, the continuous dialysis of cross-linking agent is come out, wash with water again, can get the xylogen nano-particle material in 16 hours in 70 ℃ of following vacuum-dryings, as shown in Figure 3, the xylogen nano particle is irregularly shaped, and its particle size dispersion is more even, and its grain diameter is in 20 ~ 200nm.
Embodiment 4
(1) pre-treatment of xylogen raw material: the ethanol xylogen of getting 10 parts of quality is dissolved in 180 parts of ethylene glycol, propylene glycol and glycerol (40:40:20) organic solvent it, be heated to 40 ℃, stir and xylogen was fully dissolved in 1.5 hours, remove by filter the insolubles in the raw material, obtain filtrate.
(2) preparation of xylogen colloidal sol: get 10 parts of quality above-mentioned steps (1) gained filtrate,, keep stirring to wherein dripping sulfuric acid and phosphoric acid to pH=2.0 with certain speed, obtain the xylogen colloid.
(3) crosslinking reaction: get gained xylogen colloid in 50 parts of quality steps (2), heating in water bath to 45 ℃, to the acetaldehyde that wherein drips 0.5 part of quality and glutaraldehyde cross-linking agent, stirred 2 hours, xylogen colloid and linking agent generation crosslinking reaction, question response is cooled to room temperature after finishing, to wherein dripping distilled water, the continuous dialysis of cross-linking agent is come out, use distilled water wash again, can get the xylogen nano-particle material in 18 hours in 70 ℃ of following vacuum-dryings, as shown in Figure 4, the xylogen nano particle is irregularly shaped, and its particle size dispersion is more even, and its grain diameter is in 80 ~ 200nm.
Embodiment 5
(1) pre-treatment of xylogen raw material: the ethanol xylogen of getting 20 parts of quality is dissolved in 350 parts of glycerol organic solvents it, is heated to 30 ℃, stirs xylogen fully to be dissolved in 2 hours, removes by filter the insolubles in the raw material, obtains filtrate.
(2) preparation of xylogen colloidal sol: get 20 parts of quality above-mentioned steps (1) gained filtrate, to wherein dripping hydrochloric acid is to pH=2.1, maintenance is stirred, and obtains the xylogen colloid with certain speed.
(3) crosslinking reaction: get gained xylogen colloid in 50 parts of quality steps (2), heating in water bath to 50 ℃, to the acetaldehyde that wherein drips 0.5 part of quality, propionic aldehyde and hexanedial (1:1:1) linking agent, stirred 2 hours, xylogen colloid and linking agent generation crosslinking reaction, question response is cooled to room temperature after finishing, to wherein dripping distilled water, the continuous dialysis of cross-linking agent is come out, use distilled water wash again, can get the xylogen nano-particle material in 15 hours in 65 ℃ of following vacuum-dryings, its grain diameter is in 80 ~ 180nm.
Embodiment 6
(1) pre-treatment of xylogen raw material: get the alkali lignin of 10 parts of quality and the ethanol xylogen of 10 parts of quality it is dissolved in 360 parts of methylene dichloride, ethylene glycol, propylene glycol (10/50/40) organic solvent, be heated to 45 ℃, stir and xylogen was fully dissolved in 2.5 hours, remove by filter the insolubles in the raw material, obtain filtrate.
(2) preparation of xylogen colloidal sol: get 15 parts of quality above-mentioned steps (1) gained filtrate, to wherein dripping hydrochloric acid and sulfuric acid are to pH=2.0, maintenance is stirred, and obtains the xylogen colloid with certain speed.
(3) crosslinking reaction: get gained xylogen colloid in 100 parts of quality steps (2), heating in water bath to 35 ℃, to the acetaldehyde that wherein drips 1 part of quality, glutaraldehyde and hexanedial (1:2:1) linking agent, stirred 2 hours, xylogen colloid and linking agent generation crosslinking reaction, question response is cooled to room temperature after finishing, to wherein dripping distilled water, the continuous dialysis of cross-linking agent is come out, use distilled water wash again, can get the xylogen nano-particle material in 12 hours in 80 ℃ of following vacuum-dryings, its grain diameter is in 20 ~ 160nm.
Claims (8)
1. the preparation method of an xylogen nano particle is characterized in that: earlier the xylogen raw material is carried out pre-treatment, remove the insolubles in the raw material, obtain raw material filtrate; In raw material filtrate, add mineral acid and be prepared into xylogen colloidal sol; Be 100: 1 ~ 2 to add linking agents according to xylogen colloidal sol and linking agent weight ratio at last, carried out crosslinking reaction 1 ~ 2 hour, with cross-linking agent separate out, drying obtains the xylogen nano particle; Described linking agent is by one or more mixing in the following material: acetaldehyde, propionic aldehyde, butyraldehyde, glutaraldehyde, hexanedial.
2. the preparation method of xylogen nano particle according to claim 1, it is characterized in that: described xylogen preprocessing method of raw materials is: the xylogen raw material is dissolved in the organic solvent, the weight ratio of xylogen raw material and organic solvent is 1: 18 ~ 20, be heated to 30 ~ 50 ℃ then, stir and xylogen was fully dissolved in 1 ~ 3 hour, remove by filter the insolubles in the raw material, obtain filtrate; Described xylogen raw material comprises alkali lignin and ethanol xylogen.
3. the preparation method of xylogen nano particle according to claim 2, it is characterized in that: described organic solvent comprises one or more mixing in methylene dichloride, ethylene glycol, propylene glycol, the glycerol.
4. the preparation method of xylogen nano particle according to claim 1, it is characterized in that: the preparation of described xylogen colloidal sol: dropping inorganic acid is to pH=2 ~ 2.5 in the raw material filtrate, and keep stirring, obtain the xylogen colloid, described mineral acid comprises one or more mixing in sulfuric acid, hydrochloric acid, the phosphoric acid.
5. the preparation method of xylogen nano particle according to claim 1, it is characterized in that: the temperature of described crosslinking reaction is 30 ~ 50 ℃, crosslinking reaction is cooled to room temperature after finishing, in the crosslinking reaction system, drip water, the continuous dialysis of cross-linking agent is come out, wash with water again, can get the xylogen nano-particle material in 12 ~ 18 hours in 60 ~ 80 ℃ of following vacuum-dryings.
6. the preparation method of xylogen nano particle according to claim 5, it is characterized in that: described xylogen nano particle diameter is 20 ~ 200nm.
7. the preparation method of xylogen nano particle according to claim 1 is characterized in that: described xylogen source comprises softwood, pourous wood and draft class plant.
8. the preparation method of xylogen nano particle according to claim 7 is characterized in that: described xylogen source comprises dragon spruce, Pinus massoniana Lamb, tamarack, birch, Eucalyptus, poplar, wheat straw, straw, maize straw, bagasse, reed.
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Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015089456A1 (en) | 2013-12-12 | 2015-06-18 | Solenis Technologies, L.P. | Lignin nanoparticle dispersions and methods for producing and using the same |
| CN106562933A (en) * | 2016-11-10 | 2017-04-19 | 广西大学 | Preparation method for lignin drug sustained release microspheres |
| CN106582549A (en) * | 2016-11-10 | 2017-04-26 | 广西大学 | Preparing method for monodisperse lignin microspheres |
| CN108420751A (en) * | 2018-04-12 | 2018-08-21 | 北京林业大学 | A kind of preparation method of the nano lignin particle with uvioresistant effect |
| CN109012609A (en) * | 2018-07-17 | 2018-12-18 | 北京林业大学 | A kind of lignin nanosphere environment-friendly preparation method thereof |
| CN109068654A (en) * | 2016-02-05 | 2018-12-21 | 马克斯-普朗克科学促进学会 | Lignin material as agriculture pharmaceutical carrier |
| WO2019081819A1 (en) * | 2017-10-26 | 2019-05-02 | Aalto University Foundation Sr | Aqueous lignin dispersions and methods of preparing the same |
| CN109847714A (en) * | 2019-04-04 | 2019-06-07 | 岭南师范学院 | A kind of preparation method of bagasse microballoon |
| CN110128733A (en) * | 2019-06-10 | 2019-08-16 | 浙江工业大学 | A method of nano lignin composite particles are prepared using micro passage reaction |
| WO2020109671A1 (en) | 2018-11-29 | 2020-06-04 | Aalto University Foundation Sr | Lignin particle based hydrogel and the method for preparation of lignin colloidal particles by solvent evaporation process |
| CN111484587A (en) * | 2019-01-25 | 2020-08-04 | 石河子大学 | Method for preparing lignin-based phenolic resin |
| CN112543782A (en) * | 2018-06-27 | 2021-03-23 | 维也纳科技大学 | Method for producing lignin particles |
| CN115386102A (en) * | 2022-08-19 | 2022-11-25 | 广州大学 | Phosphorized lignosulfonate nanoparticle and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015089456A1 (en) | 2013-12-12 | 2015-06-18 | Solenis Technologies, L.P. | Lignin nanoparticle dispersions and methods for producing and using the same |
| US10035928B2 (en) | 2013-12-12 | 2018-07-31 | Solenis Technologies, L.P. | Lignin nanoparticle dispersions and methods for producing and using the same |
| CN109068654A (en) * | 2016-02-05 | 2018-12-21 | 马克斯-普朗克科学促进学会 | Lignin material as agriculture pharmaceutical carrier |
| CN106562933A (en) * | 2016-11-10 | 2017-04-19 | 广西大学 | Preparation method for lignin drug sustained release microspheres |
| CN106582549A (en) * | 2016-11-10 | 2017-04-26 | 广西大学 | Preparing method for monodisperse lignin microspheres |
| US11524974B2 (en) | 2017-10-26 | 2022-12-13 | Aalto University Foundation Sr | Aqueous lignin dispersions and methods of preparing the same |
| WO2019081819A1 (en) * | 2017-10-26 | 2019-05-02 | Aalto University Foundation Sr | Aqueous lignin dispersions and methods of preparing the same |
| CN108420751A (en) * | 2018-04-12 | 2018-08-21 | 北京林业大学 | A kind of preparation method of the nano lignin particle with uvioresistant effect |
| CN112543782A (en) * | 2018-06-27 | 2021-03-23 | 维也纳科技大学 | Method for producing lignin particles |
| CN109012609A (en) * | 2018-07-17 | 2018-12-18 | 北京林业大学 | A kind of lignin nanosphere environment-friendly preparation method thereof |
| WO2020109671A1 (en) | 2018-11-29 | 2020-06-04 | Aalto University Foundation Sr | Lignin particle based hydrogel and the method for preparation of lignin colloidal particles by solvent evaporation process |
| CN111484587A (en) * | 2019-01-25 | 2020-08-04 | 石河子大学 | Method for preparing lignin-based phenolic resin |
| CN109847714A (en) * | 2019-04-04 | 2019-06-07 | 岭南师范学院 | A kind of preparation method of bagasse microballoon |
| CN110128733A (en) * | 2019-06-10 | 2019-08-16 | 浙江工业大学 | A method of nano lignin composite particles are prepared using micro passage reaction |
| CN110128733B (en) * | 2019-06-10 | 2021-07-27 | 浙江工业大学 | Method for preparing nano lignin composite particles by using microchannel reactor |
| CN115386102A (en) * | 2022-08-19 | 2022-11-25 | 广州大学 | Phosphorized lignosulfonate nanoparticle and preparation method and application thereof |
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