CN106397688A - Polymer-modified lignin dispersant and preparation method thereof - Google Patents
Polymer-modified lignin dispersant and preparation method thereof Download PDFInfo
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- CN106397688A CN106397688A CN201610763400.7A CN201610763400A CN106397688A CN 106397688 A CN106397688 A CN 106397688A CN 201610763400 A CN201610763400 A CN 201610763400A CN 106397688 A CN106397688 A CN 106397688A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F289/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds not provided for in groups C08F251/00 - C08F287/00
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
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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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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D17/00—Pigment pastes, e.g. for mixing in paints
- C09D17/003—Pigment pastes, e.g. for mixing in paints containing an organic pigment
Abstract
The invention discloses a polymer-modified lignin dispersant and a preparation method thereof. The preparation method comprises the following steps: firstly, a reaction is carried out for lignin, carbon disulfide and sodium hydroxide in order to obtain lignin sodium xanthogenate, and lignin diisopropyl xanthogenate is generated by oxidation with oxide and is used as a macro-molecular chain transferring agent; azodiisobutyronitrile is used as an initiator, at least two kinds of monomers of acrylic acid, methacrylic acid, and hydroxyethyl acrylate are added for a reaction in order to prepare grafted lignin derivatives, and the total mass of monomers which participated in the reaction is 80-150% of the mass of lignin diisopropyl xanthogenate; finally, after the reaction is completed, dried grafted lignin derivatives are dissolved in water, the pH value is adjusted to 8.0-9.0, and the polymer-modified lignin dispersant is obtained. The lignin dispersant has the advantages of good dispersion performance, and aqueous color paste prepared by the dispersant has good tinting strength and stability.
Description
Technical field
The present invention relates to a kind of pigment dispersant and preparation method thereof, more particularly, to a kind of polymer modification lignin divides
Powder and preparation method thereof, belongs to technical field of fine.
Background technology
Lignin is second largest Renewable resource in nature, is phenylpropanol containing oxo or it is derivative in a kind of molecular structure
The armaticity high polymer of thing construction unit.Lignin is processed to prepare the history of the existing many decades of dispersant, lignin
Dispersant is widely used to the fields such as pesticide, dyestuff, coating, weaving, and wherein lignosulfonates are lignin types
In main product.
Lignosulfonates rely on the Charge repulsion of pendant sulfonic acid radical ion, effectively can be distributed the group of preventing by stable particle
Poly-, the aromatic structure on its strand can form stronger absorption affinity to a lot of particle surfaces and play peptizaiton.Lignin
Although sulfonic acid dipersant is cheap, be widely used, its single varieties, impurity are many, molecular weight is less than normal, hydrophilic is too strong,
Dispersive property is general, and the aqueous color paste prepared as main dispersant using lignosulfonates, and often tinting strength, tinting power is low.
Industrial, lignin is mainly derived from " black liquor " of paper industry generation, due to the difference of paper-making pulping process, acid
Property and " black liquor " main component of obtaining of neutral pulping process be lignosulfonates, " black liquor " that alkaline pulp-making technique obtains is main
Composition is wanted to be alkaline lignin.Alkaline lignin is the same with lignin with lignosulfonates, and solvent is all benzyl third
Alkane derivatives, but due to reacting not exclusively in paper pulp, in the alkaline lignin in " black liquor " and lignosulfonates also
Containing hydroxy functional group hydrophilic in a large number, " black liquor " neutral and alkali lignin and lignosulfonates are modified, are to prepare height
The important channel of performance Lignin Dispersants.
In industrial application, the modification mode of lignin type is broadly divided into chemical functional modification and graft copolymerization
Modified.Conventional chemical functionalities modification mainly has sulfonation, acetalation, oxidizing process etc.；Grafting, copolymerization and modification is to use compound
Monomer carries out graft copolymerization to lignin monomer, thus introducing hydrophilic or oleophylic chain, improves the dispersion effect of Lignin Dispersants.
It is a kind of important coloring agent that granules of pigments is stably dispersed in the aqueous color paste formed in water-based system, dispersant
It is the important source material preparing aqueous color paste, dispersant directly affects the tinting strength, tinting power of mill base, storage to the dispersion effect of granules of pigments
The key propertys such as stability.At present lignin type is only applied in mill base industry on a small quantity, trace it to its cause mainly have with
Lower two aspects：1) poor to the dispersion effect of granules of pigments, lead to the tinting strength, tinting power of mill base relatively low；2) base material with a lot of mill base applications
Poor compatibility.
The derivant of lignin and lignin has radical reaction activity, under conditions of initiator exists, lignin
And its derivant can occur free radical graft copolymerization.Manufacture field in Lignin Dispersants, lignin is grafted
Modification is a kind of very effective approach, the United States Patent (USP) of such as Publication No. US7691982 describe a kind of to lignin grafting
The alkoxyl and anionic property functional group method to prepare dispersant.
The monomer such as graft acrylamide, acrylic acid, styrene on lignin macromolecular chain, can obtain some having property
The good polymer of energy.But the glycerol polymerization of routine cannot be avoided the situation of monomer autohemagglutination, because these monomers are causing
Also it is easy to autohemagglutination, the monomer of these autohemagglutinations often affects the dispersion effect of dispersant under agent effect.In recent years, research worker
Begin to focus on the controllable polymerization grafting mode of lignin, wherein RAFT (referred to as：RAFT) polymerization is nearest
A kind of activity/the controlling technology growing up during the last ten years, has controlled dividing using the Lignin Dispersants of this technology preparation
Sub- block structure, has preferable dispersive property to granules of pigments.But yet there are no using RAFT polymerization technique to wooden
Element carries out the report of graft modification.
Content of the invention
The present invention, in order to improve the dispersibility of Lignin Dispersants, expands it in the range in mill base field and raising property
Can, there is provided a kind of method that polymer modification based on RAFT living control polymerization technology is grafted lignin.
The present invention be employed technical scheme comprise that to solve its technical problem：
A kind of preparation method of polymer modification Lignin Dispersants, this preparation method comprises the steps：(1) it is first
Prepare lignin xanthate at ambient pressure as Macromolecular chain transfer agent, its preparation is as follows：Lignin by 8～20 parts of quality
It is hybridly prepared into the aqueous solution that lignin quality content is 40%～50% with water, subsequently by this lignin aqueous solution and 5～16
Enter in the reactor that the sodium hydroxide of part quality, the Carbon bisulfide of 5～10 parts of quality are put into agitator and temperature regulating device
Row chemical reaction, reaction temperature is 60～90 DEG C, and the response time is 4～8h, and reaction obtains lignin sodium xanthogenate after terminating；With
In above-mentioned lignin sodium xanthogenate, the peroxide of 10～20 parts of quality of Deca is reacted backward, and reaction terminates to obtain solid wood
Quality xanthate, wherein, lignin used is one of alkaline lignin or lignosulfonates；(2) secondly it is by
The lignin derivative of polymer modification graft process preparation grafting：Take gained solid lignin in 10 parts of quality step (1) yellow
Ortho esters and butanone are configured to lignin xanthate butanone solution, and this lignin xanthate butanone solution is loaded reactor
Interior, and put into the azodiisobutyronitrile of 0.02～0.08 part of quality, after logical nitrogen displacement air, it is warming up to 60～80 DEG C, add 8
The double bond reaction monomers of～15 parts of quality carry out chemical reaction, and the response time is 4～8h, and reaction obtains the wooden of grafting after terminating
Plain derivant；(3) be finally polymer modification Lignin Dispersants preparation：The lignin of gained grafting in step (2) is spread out
Biology is dried, and then the lignin derivative of this dried grafting is configured to aqueous solution, and adjust pH value be 8.0～
9.0, obtain polymer modification Lignin Dispersants.
In above-mentioned preparation method, further technical scheme is：Peroxide described in step (1) is hydrogen peroxide or mistake
Potassium sulfate, and the time for adding of this peroxide is 10～25min；Double bond reaction monomers described in step (2) are acrylic acid, first
In base acrylic acid and 2-(Acryloyloxy)ethanol at least two, preferably acrylic acid and methacrylic acid, and acrylic acid and methyl-prop
The mass ratio of olefin(e) acid is preferably 1:2～6, and the feeding sequence of acrylic acid and methacrylic acid is first to put into acrylic acid to put into first again
Base acrylate.
Disclosed herein as well is a kind of polymer modification Lignin Dispersants preparing gained by above-mentioned preparation method, should
Polymer modification Lignin Dispersants can be applicable to prepare aqueous color paste.
The method have the benefit that：The present invention adopts lignin to prepare Macromolecular chain transfer agent, and then passing through can
Inverse addition fracture chain tra nsfer (RAFT) polymerization technique prepares polymer modification lignin, wooden usually with this polymer modification
Prepared polymer modified lignin resin dispersant, using lignin as anchor fixed group, the monomer conduct such as acrylic acid in this dispersant
Solubilising groups, have preferably sterically hindered effect than common sodium lignin sulfonate, dispersion effect more preferably, and this dispersant use
Have the advantages that tinting strength, tinting power is high, stability is high, versatility is wide in preparing aqueous color paste.
Specific embodiment
With reference to embodiment, advantages of the present invention and distinguishing feature are expanded on further, but are not the limit to the present invention
Fixed, especially the data in embodiment is not intended to limit the consumption of each composition in invention.In embodiment used alkalescence lignin and
" black liquor " that lignosulfonates produce both from paper industry.
Dispersant prepares embodiment
Embodiment 1
The lignosulfonates of 10 parts of quality and water are hybridly prepared into the water that lignosulfonates mass content is 40%
Solution, then in the case of normal pressure leads to nitrogen, adds above-mentioned lignin sulfonic acid saline solution, the hydrogen of 5 parts of quality in reactor
The Carbon bisulfide of sodium oxide and 5 parts of quality carries out chemical reaction, and controlling reaction temperature is 70 DEG C, and the response time is 6h, subsequently uses
10min drips the hydrogen peroxide of 10 parts of quality.With 2-3 lignin xanthate of distilled water wash, place 45 DEG C of vacuum drying
Case is dried.Load the dried lignin xanthate of 10 parts of quality toward in flask, plus butanone prepares 50% lignin xanthan
The butanone solution of acid esters mass content, plus the azodiisobutyronitrile of 0.02 part of quality, after logical nitrogen displacement air, start to warm up to
60 DEG C, subsequently it is slowly added dropwise the acrylic monomerss of 2.5 parts of quality, after dripping, then the methacrylic acid list of 5.5 parts of quality of Deca
Body.The accumulative response time is 6h.Reaction is vacuum dried after terminating, and is subsequently added distilled water and prepares the wooden of effective point 40% of quality
Plain dispersant, and adjust pH value for 8.0 with sodium hydroxide solution.
Embodiment 2
The lignosulfonates of 20 parts of quality and water are hybridly prepared into the water that lignosulfonates mass content is 40%
Solution, then in the case of normal pressure leads to nitrogen, adds above-mentioned lignin sulfonic acid saline solution, the hydrogen of 16 parts of quality in reactor
The Carbon bisulfide of sodium oxide and 7 parts of quality carries out chemical reaction, and controlling reaction temperature is 60 DEG C, and the response time is 4h, subsequently uses
15min drips the hydrogen peroxide of 20 parts of quality.With 2-3 lignin xanthate of distilled water wash, place 45 DEG C of vacuum drying
Case is dried.Load the dried lignin xanthate of 10 parts of quality toward in flask, plus butanone prepares 50% lignin xanthan
The butanone solution of acid esters mass content, plus the azodiisobutyronitrile of 0.04 part of quality, after logical nitrogen displacement air, start to warm up to
80 DEG C, subsequently it is slowly added dropwise the acrylic monomerss of 3 parts of quality, after dripping, then the methacrylic acid monomer of 12 parts of quality of Deca.
The accumulative response time is 4h.Reaction terminates rear dry resin, is subsequently added distilled water and prepares the lignin that quality effectively divides 40%
Dispersant, and adjust pH value for 8.0 with sodium hydroxide solution.
Embodiment 3
The alkaline lignin of 15 parts of quality and water are hybridly prepared into the aqueous solution that alkaline lignin quality content is 50%,
Then normal pressure lead to nitrogen in the case of, add in reactor above-mentioned alkalescence lignin aqueous solution, the sodium hydroxide of 8 parts of quality and
The Carbon bisulfide of 10 parts of quality carries out chemical reaction, and controlling reaction temperature is 90 DEG C, and the response time is 5h, is subsequently dripped with 25min
Add the hydrogen peroxide of 12 parts of quality.With 2-3 lignin xanthate of distilled water wash, place 45 DEG C of vacuum drying ovens and be dried.
Load the dried lignin xanthate of 10 parts of quality toward in flask, plus butanone prepares 50% lignin xanthate quality
The butanone solution of content, the azodiisobutyronitrile of 0.08 part of quality, after logical nitrogen displacement air, start to warm up to 75 DEG C, subsequently
It is slowly added dropwise the acrylic monomerss of 2 parts of quality, after dripping, then the methacrylic acid monomer of 6 parts of quality of Deca.During accumulative reaction
Between be 7h.Reaction terminates rear dry resin, is subsequently added distilled water and prepares the Lignin Dispersants that quality effectively divides 40%, is used in combination
It is 8.0 that sodium hydroxide solution adjusts pH value.
Embodiment 4
The alkaline lignin of 10 parts of quality and water are hybridly prepared into the aqueous solution that alkaline lignin quality content is 40%,
Then, in the case of normal pressure leads to nitrogen, above-mentioned alkalescence lignin aqueous solution, the sodium hydroxide of 10 parts of quality are added in reactor
Carry out chemical reaction with the Carbon bisulfide of 7 parts of quality, controlling reaction temperature is 60 DEG C, the response time is 8h, is subsequently dripped with 15min
Add the potassium peroxydisulfate of 12 parts of quality.With 2-3 lignin xanthate of distilled water wash, place 45 DEG C of vacuum drying ovens and do
Dry.Load the lignin xanthate of 10 parts of dried quality toward in flask, plus butanone prepares 50% lignin xanthate
The butanone solution of mass content, the azodiisobutyronitrile of 0.06 part of quality, after logical nitrogen displacement air, start to warm up to 70 DEG C,
Subsequently it is slowly added dropwise the acrylic monomerss of 3 parts of quality, after dripping, then the methacrylic acid monomer of 6 parts of quality of Deca.Accumulative anti-
It is 4h between seasonable.Reaction terminates rear dry resin, is subsequently added distilled water and prepares the Lignin Dispersants that quality effectively divides 40%,
And adjust pH value for 9.0 with sodium hydroxide solution.
Embodiment 5
By the lignosulfonates of 8 parts of quality and water be hybridly prepared into lignosulfonates mass content be 45% water-soluble
Liquid, then in the case of normal pressure leads to nitrogen, adds above-mentioned lignin sulfonic acid saline solution, the hydrogen-oxygen of 10 parts of quality in reactor
Change sodium and the Carbon bisulfide of 10 parts of quality carries out chemical reaction, controlling reaction temperature is 80 DEG C, the response time is 7h, subsequently uses
15min drips the hydrogen peroxide of 12 parts of quality.With 2-3 lignin xanthate of distilled water wash, place 45 DEG C of vacuum drying
Case is dried.Load the lignin xanthate of 10 parts of dried quality toward in flask, plus butanone prepares 50% lignin xanthan
The butanone solution of acid esters mass content, the azodiisobutyronitrile of 0.06 part of quality, after logical nitrogen displacement air, start to warm up to 70
DEG C, subsequently it is slowly added dropwise the acrylic monomerss of 3 parts of quality, after dripping, then the methacrylic acid monomer of 7 parts of quality of Deca,
The hydroxyethyl acrylate monomers of 5 parts of quality of Deca afterwards.The accumulative response time is 4h.Reaction terminates rear dry resin, adds distillation
Water prepares the Lignin Dispersants that quality effectively divides 40%, and adjusts pH value for 8.5 with sodium hydroxide solution.
Application Example
The general commercial sodium lignin sulfonate of the Lignin Dispersants of 5 embodiment preparations and 2 purchases is used for phthalein
Cyanines are blue to starch dispersion grinding test, illustrates effect, the formula composition of Application Example and grinding as 7 Application Examples
State is as shown in table 1 below：
Table 1. Application Example 1-6 formula composition and grinding state
As shown in table 1, through the general commercial of 5 embodiment Lignin Dispersants provided by the present invention all relatively purchases
The dispersive property of sodium lignin sulfonate is good, the phthalocyanine blue mill base of the general commercial sodium lignin sulfonate preparation of purchase, and state is glued
Thick it is difficult to disperse.
Tested and assessed by mill base prepared by above-mentioned Application Example 1,2,3,4,5,7 and analyzed, according to HG/T
3951-2007 Appendix B tests the relative color strength of the aqueous color paste of Application Example 1,2,3,4,5,7 preparation, with application implementation
Example 7 prepares mill base on the basis of mill base, and its tinting strength, tinting power is 100%；By range estimation, observe aqueous color paste airtight placement 90 at 25 DEG C
After it, have or not the situation occurring that obvious granules of pigments precipitation, flocculation etc. have a strong impact on stability, " √ " represents that range estimation is without exception,
"×" represents that obvious granules of pigments precipitation, flocculation situation in range estimation；Swashed with the MS2000 of Malvern Instr Ltd. of Britain
Light micron grain size instrument tests the particle diameter distribution of the aqueous color paste of Application Example 1,2,3,4,5,7 preparation, in test result, D50
The minimum grain size that in the surveyed granule of expression, 50% particle can be transferred through；With NDJ-1 type rotating cylinder viscometer, using No. 3 rotors, survey
Examination viscosity under 30r/min for the mill base；Grinding property of the finger test of mill base and coating is the crucial examination judging mill base and paint compatibility
Test, it is by after uniform to mill base and coating mixing, using wet film maker, mixed mill base is existed with coating compound blade coating
On cardboard, before film is quick-drying, ground in film local with finger, after dried coating film, compare finger grind part and other
A kind of method of partial color distinction, then thinks mill base and coating in the case of seeing obvious aberration after generally referring to grind
Poor compatibility, no substantially aberration then thinks that the compatibility is good, and by Application Example 1-5, the aqueous color paste of 7 preparations and industry apply
Material, water-based industrial paint account for after paint film gross mass 1% ratio mix homogeneously according to pigment, carry out finger and grind experiment, assessment mill base and work
Industry coating, the compatibility of water-based industrial paint.Its characterization result is as shown in table 2：
Table 2. Application Example prepares the test result of mill base
For the ordinary skill in the art, specific embodiment is simply exemplarily described to the present invention,
Obviously the present invention implements and is not subject to the restrictions described above, as long as employ method of the present invention design entering with technical scheme
The improvement of the various unsubstantialities of row, or the not improved design by the present invention and technical scheme directly apply to other occasions
, all within protection scope of the present invention.
Claims (8)
1. a kind of preparation method of polymer modification Lignin Dispersants is it is characterised in that comprise the steps：
(1) preparation of Macromolecular chain transfer agent：The lignin of 8～20 parts of quality and water are hybridly prepared into lignin quality content
Aqueous solution for 40%～50%, subsequently by the sodium hydroxide of this lignin aqueous solution and 5～16 parts of quality, 5～10 parts of quality
Carbon bisulfide put into agitator and temperature regulating device reactor in carry out chemical reaction, reaction temperature is 60～90
DEG C, the response time is 4～8h, and reaction obtains lignin sodium xanthogenate after terminating；Drip then in above-mentioned lignin sodium xanthogenate
Plus 10～peroxide of 20 parts of quality reacted, and reaction terminates to obtain solid lignin xanthate, wherein, used wooden
Element is one of alkaline lignin or lignosulfonates；
(2) preparation of the lignin derivative being grafted：Take gained solid lignin xanthate and fourth in 10 parts of quality step (1)
Ketone is configured to lignin xanthate butanone solution, this lignin xanthate butanone solution is loaded in reactor, and puts into
The azodiisobutyronitrile of 0.02～0.08 part of quality, after logical nitrogen displacement air, is warming up to 60～80 DEG C, adds 8～15 parts of matter
The double bond reaction monomers of amount carry out chemical reaction, and the response time is 4～8h, and the lignin that reaction obtains after terminating being grafted derives
Thing；
(3) preparation of polymer modification Lignin Dispersants：The lignin derivative of gained grafting in step (2) is done
Dry, then the lignin derivative of this dried grafting is configured to aqueous solution, and adjusts pH value for 8.0～9.0, gathered
Polymer modified Lignin Dispersants.
2. polymer modification Lignin Dispersants according to claim 1 preparation method it is characterised in that：Step (1)
Described in peroxide be hydrogen peroxide or potassium peroxydisulfate, and the time for adding of this peroxide be 10～25min.
3. polymer modification Lignin Dispersants according to claim 1 preparation method it is characterised in that：Step (2)
Described in double bond reaction monomers be acrylic acid, in methacrylic acid and 2-(Acryloyloxy)ethanol at least two.
4. polymer modification Lignin Dispersants according to claim 3 preparation method it is characterised in that：Step (2)
Described in double bond reaction monomers be acrylic acid and methacrylic acid.
5. polymer modification Lignin Dispersants according to claim 4 preparation method it is characterised in that：Step (2)
Described in acrylic acid and methacrylic acid mass ratio be 1:2～6.
6. polymer modification Lignin Dispersants according to claim 5 preparation method it is characterised in that：Step (2)
The feeding sequence of middle double bond reaction monomers is first to put into acrylic acid to put into methacrylate again.
7. in a kind of claim 1 to 6, preparation method described in any claim is prepared the polymer modification lignin of gained and is divided
Powder.
8. application in preparing aqueous color paste for the polymer modification Lignin Dispersants described in a kind of claim 7.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108384028A (en) * | 2018-02-05 | 2018-08-10 | 中国林业科学研究院林产化学工业研究所 | A kind of synthetic method of lignin xanthate macromolecular RAFT agent |
| CN110078938A (en) * | 2019-05-23 | 2019-08-02 | 中国林业科学研究院林产化学工业研究所 | A kind of water-soluble lignin base chain-transferring agent and preparation method thereof |
| CN111303949A (en) * | 2018-04-16 | 2020-06-19 | 李智 | Preparation method of modified asparagus coal water slurry additive |
| CN114933785A (en) * | 2022-04-29 | 2022-08-23 | 上海昶法新材料有限公司 | Modified lignin/PBAT biodegradable plastic and preparation method thereof |
| CN115160512A (en) * | 2022-08-19 | 2022-10-11 | 安徽农业大学 | Lignin-based thermoplastic elastomer with rapid repair function and preparation method thereof |
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| CN111303949A (en) * | 2018-04-16 | 2020-06-19 | 李智 | Preparation method of modified asparagus coal water slurry additive |
| CN110078938A (en) * | 2019-05-23 | 2019-08-02 | 中国林业科学研究院林产化学工业研究所 | A kind of water-soluble lignin base chain-transferring agent and preparation method thereof |
| CN114933785A (en) * | 2022-04-29 | 2022-08-23 | 上海昶法新材料有限公司 | Modified lignin/PBAT biodegradable plastic and preparation method thereof |
| CN115160512A (en) * | 2022-08-19 | 2022-10-11 | 安徽农业大学 | Lignin-based thermoplastic elastomer with rapid repair function and preparation method thereof |
| CN115160512B (en) * | 2022-08-19 | 2024-01-30 | 安徽农业大学 | Lignin-based thermoplastic elastomer with rapid repair function and preparation method thereof |
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