CN106188434A - A kind of preparation method of lignin base hydrogel - Google Patents
A kind of preparation method of lignin base hydrogel Download PDFInfo
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- CN106188434A CN106188434A CN201610549070.1A CN201610549070A CN106188434A CN 106188434 A CN106188434 A CN 106188434A CN 201610549070 A CN201610549070 A CN 201610549070A CN 106188434 A CN106188434 A CN 106188434A
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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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/56—Polymerisation initiated by wave energy or particle radiation by ultrasonic vibrations
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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
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
- C08J3/075—Macromolecular gels
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2351/00—Characterised by the use of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
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Abstract
The invention provides the preparation method of a kind of lignin base hydrogel, comprise the steps: that weighing sodium hydroxide is in small beaker, adding deionized water makes sodium hydroxide dissolve, it is placed in ice-water bath, pipette acrylic acid solution and be added dropwise over sodium hydroxide solution under being stirred continuously, after completion of the reaction, mixed liquor A is obtained；Weigh anhydride in small beaker, add ammonia and carry out ammoniation modified, after completion of the reaction, obtain mixed liquid B；Mixed liquor A is mixed with mixed liquid B, obtains mixed liquor C, add lignosulfonates, Ammonium persulfate. and N, N methylene-bisacrylamide, be stirred continuously, dissolve completely, obtain mixed liquor D；Mixed liquor D is sealed, ultrasonic reaction under constant temperature, take out product after having reacted and shred into bulk, processing by soaked in absolute ethyl alcohol；Product after immersion treatment is placed vacuum drying, pulverizes, obtain lignin base hydrogel, preserve.The lignin base hydrogel preparation method of the present invention, technological process is simple, easily operated, with low cost.
Description
Technical field
The present invention relates to the preparation method of a kind of lignin base hydrogel, relate generally to a kind of with sodium lignin sulfonate for grafting
Thing, utilizes the preparation method of ultrasonic method synthesis lignin base hydrogel.
Background technology
Lignosulfonates are that one of principal by product of paper-making pulping industry, only China the most just have millions of tons wooden
Element sulfonate produces, and a most little part is obtained by, therefore, and active development lignin sulfonic acid product salt, constantly
Widen its range of application, not only improve environmental protection, be also beneficial to the utilization of resource.About 50 benzene oxide unit groups on its molecule
Become is similar to spherical three-dimensional net structure body, and centre is the log quality three-dimensional net structure of unsulfonated, central periphery
Being dispersed with and be hydrolyzed and contain sulfonic side chain, outermost layer is formed electric double layer by sulfonic counter ion.On its molecular structure
Containing various functional groups such as hydroxyl, sulfonic group and methoxyl groups, with many kinds of substance, multiple modified-reaction can occur under certain condition
Such as sulfonating agent sulfonation, there are oxidizing, complexing of metal ion or grafting etc..At present, lignosulfonates are extensively used as glue
Stick, rubber reinforcing filler, surfactant, soil quality stabilizing agent, water treatment agent etc..
Hydrogel is to be formed by hydrophilic crosslinked polymer, water insoluble, but can be swelling in water, is that a class has three
Tie up cancellated functional material.It can absorb and reach deadweight hundreds times or even the moisture of thousands of times, and in certain pressure and temperature
Internal moisture can also be made under Du to be maintained, there is excellent weatherability and protect fluidity.In health care, construction material, agricultural
Gardening, food industry and the field such as petrochemical industry and environmental conservation are widely applied.At present, hydrogel is many with propylene
Acid, acrylamide are the copolymerizations such as monomer and natural polymer such as cellulose, each kind of starch, mineral.But, acrylamide
Material price is high and toxic, and it is particularly important for therefore finding suitable acrylamide sub.Maleic anhydride is work
Preparing the common used material of various types of resins in industry, relative to acrylamide, its material price and toxicity all decrease, and pass through ammonia
Modified acrylamide perfect can be replaced to prepare hydrogel as monomer.Meanwhile, connect with trade waste sodium lignin sulfonate
Branch copolymerization, can not only improve environment, and paper making waste huge profit is used, additionally it is possible to improve hydrogel property indices.
Summary of the invention
It is an object of the invention to use acrylic acid and ammonification maleic anhydride is primary raw material, graft copolymerization sulfomethylated lignin
Acid sodium, synthesizes lignin base hydrogel by ultrasonic method, and technique is green simple, and raw material is easy to get, with low cost and can repeat profit
With papermaking waste, reduce ambient pressure, be suitable to industrialized production.
Technical scheme is as follows:
The preparation method of a kind of lignin base hydrogel, comprises the steps:
Under step 1, room temperature, weighing sodium hydroxide, in small beaker, adds deionized water and makes sodium hydroxide fully dissolve,
To sodium hydroxide solution, sodium hydroxide solution is placed in ice-water bath, pipettes acrylic acid solution and be added dropwise under being stirred continuously
Sodium hydroxide solution, after completion of the reaction, obtains mixed liquor A, set aside for use；
Step 2, weigh anhydride in small beaker, add ammonia and carry out ammoniation modified, after completion of the reaction, obtain mixed liquid B,
Set aside for use；
The mixed liquid B that step 3, mixed liquor A step 1 obtained obtain with step 2 mixes, and obtains mixed liquor C, to mixing
Liquid C is sequentially added into lignosulfonates, Ammonium persulfate. and N,N methylene bis acrylamide, is stirred continuously, make sulfomethylated lignin
Hydrochlorate, Ammonium persulfate. and N,N methylene bis acrylamide dissolve completely, obtain mixed liquor D；
Step 4, the mixed liquor D that step 3 is obtained seal transfer ultrasonic cleaner in, under constant temperature ultrasonic instead
Should, take out product after having reacted and shred into bulk, processing by soaked in absolute ethyl alcohol；
Step 5, the product after immersion treatment is placed in vacuum drying oven drying, carries out pulverization process with pulverizer,
Obtain end product lignin base hydrogel, be positioned in exsiccator preservation.
In step 1, during preparation mixed liquor A, the mass fraction of the sodium hydroxide solution used is 0.42g/mL, is used
The volume ratio of acrylic acid solution and deionized water be 1:1, the concentration of the acrylic acid solution used is 14.57mol/L.
In step 2, during preparation mixed liquid B, described anhydride is maleic anhydride, the mass fraction of the ammonia used
It is 25%；Described maleic anhydride is 0.05～0.55g:2～10mL with the amount ratio of ammonia.
In step 3, when preparing mixed liquor C, the deionized water in mixed liquor A with the volume ratio of the ammonia in mixed liquid B is
5:2～10；When preparing mixed liquor D, the lignosulfonates that used, Ammonium persulfate., N,N methylene bis acrylamide are with mixed
The mass ratio closing the sodium hydroxide in liquid A is 0.01～0.11:0.0262～0.1575:0.0013～0.0262:2.1.
In step 3, the lignosulfonates used are sodium lignin sulfonate.
In step 4, described constant temperature is 50～60 DEG C, and ultrasonic time is 3h, with the time of soaked in absolute ethyl alcohol is
24h。
Beneficial effect:
The present invention is with acrylic acid, ammonification maleic anhydride as monomer, by adding sodium lignin sulfonate, cross-linking agent and drawing
Send out agent, utilize ultrasonic method to prepare lignin base hydrogel.Result display technological process is simple, easily operated, with low cost, also simultaneously
Achieve the greenization of synthesis technique and the efficient utilization of trade waste sodium lignin sulfonate.Prepared swelling behavior is inhaled
Attached functional, it is suitable for industrialized production.
Accompanying drawing explanation
Fig. 1 is the infrared figure of embodiment 4 sample；
Fig. 2 is the scanning electron microscope (SEM) photograph of embodiment 4 sample.
Detailed description of the invention
Below in conjunction with being embodied as example, the present invention will be further described, so that those skilled in the art are more fully understood that
The present invention, but the invention is not limited in following example.
Embodiment 1
Room temperature calls 2.1g sodium hydroxide in the following text in small beaker, adds 5ml deionized water and makes it fully dissolve, is placed in ice-water bath
In, accurately pipette 5ml 14.57mol/L acrylic acid solution under being stirred continuously, be dropwise slowly added to sodium hydroxide solution, weigh
0.05g maleic anhydride, in small beaker, adds the ammonia that 2ml mass fraction is 25% and carries out aminating reaction, fully react
After, by above-mentioned two small beaker solution mixing, it is sequentially added into 0.01g sodium lignin sulfonate, 0.0262g persulfuric acid the most in order
Ammonium, 0.0079g N,N methylene bis acrylamide, it is stirred continuously so that it is after dissolving completely, sealing transfer is put KQ-100B type and is surpassed
In sound wave washer, control water temperature, 50～60 DEG C of temperature, is taken out product and shreds frustillatum, with anhydrous after ultrasonic reaction 3h
Soak with ethanol 24h；Product after immersion treatment is placed in vacuum drying oven and dries to constant weight, carry out at pulverizing with pulverizer
Reason, then collects and places preservation in exsiccator.
Embodiment 2
Room temperature calls 2.1g sodium hydroxide in the following text in small beaker, adds 5ml deionized water and makes it fully dissolve, is placed in ice-water bath
In, accurately pipette 5ml 14.57mol/L acrylic acid solution under being stirred continuously, be dropwise slowly added to sodium hydroxide solution, weigh
0.15g maleic anhydride, in small beaker, adds the ammonia that 4ml mass fraction is 25% and carries out aminating reaction, fully react
After, by above-mentioned two small beaker solution mixing, it is sequentially added into 0.03g sodium lignin sulfonate, 0.0525g persulfuric acid the most in order
Ammonium, 0.0132g N,N methylene bis acrylamide, it is stirred continuously so that it is after dissolving completely, sealing transfer is put KQ-100B type and is surpassed
In sound wave washer, control water temperature, 50～60 DEG C of temperature, is taken out product and shreds frustillatum, with anhydrous after ultrasonic reaction 3h
Soak with ethanol 24h；Product after immersion treatment is placed in vacuum drying oven and dries to constant weight, carry out at pulverizing with pulverizer
Reason, then collects and places preservation in exsiccator.
Embodiment 3
Room temperature calls 2.1g sodium hydroxide in the following text in small beaker, adds 5ml deionized water and makes it fully dissolve, is placed in ice-water bath
In, accurately pipette 5ml 14.57mol/L acrylic acid solution under being stirred continuously, be dropwise slowly added to sodium hydroxide solution, weigh
0.45g maleic anhydride, in small beaker, adds the ammonia that 6ml mass fraction is 25% and carries out aminating reaction, fully react
After, by above-mentioned two small beaker solution mixing, it is sequentially added into 0.07g sodium lignin sulfonate, 0.1575g persulfuric acid the most in order
Ammonium, 0.0013g N,N methylene bis acrylamide, it is stirred continuously so that it is after dissolving completely, sealing transfer is put KQ-100B type and is surpassed
In sound wave washer, control water temperature, 50～60 DEG C of temperature, is taken out product and shreds frustillatum, with anhydrous after ultrasonic reaction 3h
Soak with ethanol 24h；Product after immersion treatment is placed in vacuum drying oven and dries to constant weight, carry out at pulverizing with pulverizer
Reason, then collects and places preservation in exsiccator.
Embodiment 4
Room temperature calls 2.1g sodium hydroxide in the following text in small beaker, adds 5ml deionized water and makes it fully dissolve, is placed in ice-water bath
In, accurately pipette 5ml 14.57mol/L acrylic acid solution under being stirred continuously, be dropwise slowly added to sodium hydroxide solution, weigh
0.25g maleic anhydride, in small beaker, adds the ammonia that 8ml mass fraction is 25% and carries out aminating reaction, fully react
After, by above-mentioned two small beaker solution mixing, it is sequentially added into 0.05g sodium lignin sulfonate, 0.0787g persulfuric acid the most in order
Ammonium, 0.0026g N,N methylene bis acrylamide, it is stirred continuously so that it is after dissolving completely, sealing transfer is put KQ-100B type and is surpassed
In sound wave washer, control water temperature, 50～60 DEG C of temperature, is taken out product and shreds frustillatum, with anhydrous after ultrasonic reaction 3h
Soak with ethanol 24h；Product after immersion treatment is placed in vacuum drying oven and dries to constant weight, carry out at pulverizing with pulverizer
Reason, then collects and places preservation in exsiccator.
In Fig. 1,3459cm-1For O-H stretching vibration absworption peak, 2953cm-1Place is C-H stretching vibration absworption peak, 1567cm-1Place is the C-N characteristic absorption peak of amide.The C=O absworption peak of acrylic acid and acrylamide occurs in 1719cm-1And occur in
1464cm-1Be COO in sodium acrylate-Anion absorption peak.This explanation maleic anhydride successfully by ammonia institute's ammonification and
Generate-COO-With-CONH2Group.Additionally, the sulfonic group-SO of sodium lignin sulfonate3H and Syringa oblata Lindl. group characteristic peak exist
1175cm-1And 1123cm-1Place is the most also found.This demonstrate that sodium lignin sulfonate and acrylic acid and ammonification maleic acid
Anhydride monomer the most successfully there occurs graft copolymerization, and the SL-P (AA-co-AMA) of synthesis is sodium lignin sulfonate, acrylic acid
Complex with ammonification maleic anhydride.
In Fig. 2, there is substantial amounts of fold in hydrogel surface, and this is the addition due to sodium lignin sulfonate, in hydrogel network
Network is formed hydrone passage.And the fold on this surface makes hydrogel have bigger specific surface area, beneficially water absorbing capacity
The raising of power.
Embodiment 5
Room temperature calls 2.1g sodium hydroxide in the following text in small beaker, adds 5ml deionized water and makes it fully dissolve, is placed in ice-water bath
In, accurately pipette 5ml 14.57mol/L acrylic acid solution under being stirred continuously, be dropwise slowly added to sodium hydroxide solution, weigh
0.55g maleic anhydride, in small beaker, adds the ammonia that 10ml mass fraction is 25% and carries out aminating reaction, fully react
After, by above-mentioned two small beaker solution mixing, it is sequentially added into 0.11g sodium lignin sulfonate, 0.1312g persulfuric acid the most in order
Ammonium, 0.0262g N,N methylene bis acrylamide, it is stirred continuously so that it is after dissolving completely, sealing transfer is put KQ-100B type and is surpassed
In sound wave washer, control water temperature, 50～60 DEG C of temperature, is taken out product and shreds frustillatum, with anhydrous after ultrasonic reaction 3h
Soak with ethanol 24h；Product after immersion treatment is placed in vacuum drying oven and dries to constant weight, carry out at pulverizing with pulverizer
Reason, then collects and places preservation in exsiccator.
Claims (6)
1. the preparation method of a lignin base hydrogel, it is characterised in that comprise the steps:
Under step 1, room temperature, weighing sodium hydroxide, in small beaker, adds deionized water and makes sodium hydroxide fully dissolve, obtain hydrogen
Sodium hydroxide solution, is placed in sodium hydroxide solution in ice-water bath, pipettes acrylic acid solution and is added dropwise over hydrogen-oxygen under being stirred continuously
Change sodium solution, after completion of the reaction, obtain mixed liquor A, set aside for use；
Step 2, weigh anhydride in small beaker, add ammonia and carry out ammoniation modified, after completion of the reaction, obtain mixed liquid B, stand
Stand-by；
The mixed liquid B that step 3, mixed liquor A step 1 obtained obtain with step 2 mixes, and obtains mixed liquor C, to mixed liquor C
In be sequentially added into lignosulfonates, Ammonium persulfate. and N,N methylene bis acrylamide, be stirred continuously, make lignin sulfonic acid
Salt, Ammonium persulfate. and N,N methylene bis acrylamide dissolve completely, obtain mixed liquor D；
Step 4, mixed liquor D step 3 obtained seal in transfer ultrasonic cleaner, ultrasonic reaction under constant temperature, instead
Product should be taken out after completing and shred into bulk, process by soaked in absolute ethyl alcohol；
Step 5, the product after immersion treatment is placed in vacuum drying oven drying, carries out pulverization process with pulverizer, obtain
End product lignin base hydrogel, is positioned in exsiccator preservation.
2. according to the preparation method of a kind of lignin base hydrogel described in claim 1, it is characterised in that in step 1, preparation
During mixed liquor A, the mass fraction of the sodium hydroxide solution used is 0.42g/mL, the acrylic acid solution used and deionization
The volume ratio of water is 1:1, and the concentration of the acrylic acid solution used is 14.57mol/L.
3. according to the preparation method of a kind of lignin base hydrogel described in claim 1, it is characterised in that in step 2, preparation
During mixed liquid B, described anhydride is maleic anhydride, and the mass fraction of the ammonia used is 25%；Described maleic two
Anhydride is 0.05～0.55g:2～10mL with the amount ratio of ammonia.
4. according to the preparation method of a kind of lignin base hydrogel described in claim 1, it is characterised in that in step 3, preparation
During mixed liquor C, the deionized water in mixed liquor A is 5:2～10 with the volume ratio of the ammonia in mixed liquid B；Prepare mixed liquor D
Time, lignosulfonates, Ammonium persulfate., N,N methylene bis acrylamide and the sodium hydroxide in mixed liquor A used
Mass ratio is 0.01～0.11:0.0262～0.1575:0.0013～0.0262:2.1.
5. according to the preparation method of a kind of lignin base hydrogel described in claim 1, it is characterised in that in step 3, made
Lignosulfonates be sodium lignin sulfonate.
6. according to the preparation method of a kind of lignin base hydrogel described in claim 1, it is characterised in that in step 4, described
Constant temperature be 50～60 DEG C, ultrasonic time is 3h, is 24h with the time of soaked in absolute ethyl alcohol.
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108314868A (en) * | 2018-03-21 | 2018-07-24 | 中南林业科技大学 | A kind of lignin composite hydrogel and preparation method thereof |
| CN110092921A (en) * | 2019-05-22 | 2019-08-06 | 陕西科技大学 | A kind of preparation method of the regulatable high-intensity wood quality hydrogel of mechanical property |
| CN110372832A (en) * | 2019-06-17 | 2019-10-25 | 江苏大学 | A kind of preparation method and application of lignin-base macromolecule resin adsorbent |
| CN110746557A (en) * | 2019-10-29 | 2020-02-04 | 中国林业科学研究院林产化学工业研究所 | Lignin composite hydrogel with high elasticity and fatigue strength resistance and preparation method thereof |
| CN111261878A (en) * | 2020-01-23 | 2020-06-09 | 同济大学 | Catalyst slurry containing aqueous gel, catalyst layer and fuel cell electrode produced therefrom |
| CN111410752A (en) * | 2019-01-04 | 2020-07-14 | 华南农业大学 | Hydrogel nanocomposite and preparation method and application thereof |
| CN113509907A (en) * | 2021-03-09 | 2021-10-19 | 大连工业大学 | Preparation of lignin-based composite hydrogel and application of lignin-based composite hydrogel in heavy metal ion adsorption and luminescent materials |
| CN113751492A (en) * | 2021-09-10 | 2021-12-07 | 华南农业大学 | Method for repairing organic contaminated soil by using magnetic lignin hydrogel to activate persulfate |
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2016
- 2016-07-12 CN CN201610549070.1A patent/CN106188434A/en active Pending
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108314868A (en) * | 2018-03-21 | 2018-07-24 | 中南林业科技大学 | A kind of lignin composite hydrogel and preparation method thereof |
| CN111410752A (en) * | 2019-01-04 | 2020-07-14 | 华南农业大学 | Hydrogel nanocomposite and preparation method and application thereof |
| CN111410752B (en) * | 2019-01-04 | 2021-11-26 | 华南农业大学 | Hydrogel nanocomposite and preparation method and application thereof |
| CN110092921A (en) * | 2019-05-22 | 2019-08-06 | 陕西科技大学 | A kind of preparation method of the regulatable high-intensity wood quality hydrogel of mechanical property |
| CN110092921B (en) * | 2019-05-22 | 2022-05-03 | 陕西科技大学 | Preparation method of high-strength lignin hydrogel with adjustable mechanical properties |
| CN110372832A (en) * | 2019-06-17 | 2019-10-25 | 江苏大学 | A kind of preparation method and application of lignin-base macromolecule resin adsorbent |
| CN110372832B (en) * | 2019-06-17 | 2021-09-10 | 江苏大学 | Preparation method and application of lignin-based polymeric resin adsorbent |
| CN110746557A (en) * | 2019-10-29 | 2020-02-04 | 中国林业科学研究院林产化学工业研究所 | Lignin composite hydrogel with high elasticity and fatigue strength resistance and preparation method thereof |
| CN111261878A (en) * | 2020-01-23 | 2020-06-09 | 同济大学 | Catalyst slurry containing aqueous gel, catalyst layer and fuel cell electrode produced therefrom |
| CN113509907A (en) * | 2021-03-09 | 2021-10-19 | 大连工业大学 | Preparation of lignin-based composite hydrogel and application of lignin-based composite hydrogel in heavy metal ion adsorption and luminescent materials |
| CN113509907B (en) * | 2021-03-09 | 2024-03-22 | 大连工业大学 | Preparation of lignin-based composite hydrogel and application of lignin-based composite hydrogel in heavy metal ion adsorption and luminescent materials |
| CN113751492A (en) * | 2021-09-10 | 2021-12-07 | 华南农业大学 | Method for repairing organic contaminated soil by using magnetic lignin hydrogel to activate persulfate |
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