CN112934206A - Modified lignin polyurethane adsorbent and preparation method thereof - Google Patents
Modified lignin polyurethane adsorbent and preparation method thereof Download PDFInfo
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- CN112934206A CN112934206A CN202110384461.3A CN202110384461A CN112934206A CN 112934206 A CN112934206 A CN 112934206A CN 202110384461 A CN202110384461 A CN 202110384461A CN 112934206 A CN112934206 A CN 112934206A
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
- B01J20/262—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon to carbon unsaturated bonds, e.g. obtained by polycondensation
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/24—Naturally occurring macromolecular compounds, e.g. humic acids or their derivatives
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28014—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their form
- B01J20/28042—Shaped bodies; Monolithic structures
- B01J20/28045—Honeycomb or cellular structures; Solid foams or sponges
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
- C08G18/6492—Lignin containing materials; Wood resins; Wood tars; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/04—Carbon
- C08K3/041—Carbon nanotubes
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G25/00—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents
- C10G25/003—Specific sorbent material, not covered by C10G25/02 or C10G25/03
Abstract
The invention relates to the technical field of bio-based high polymer materials, in particular to a modified lignin polyurethane adsorbent and a preparation method thereof, wherein (1) 15-45 parts of lignin, 100 parts of polyol and 2.25-6.75 parts of concentrated sulfuric acid are subjected to a dehydration reaction to obtain lignin polyol; (2) taking 25-35 parts of lignin polyol prepared in the step (1), stirring and mixing with 0.2-0.4 part of catalyst, 0.06-0.12 part of foaming agent and 0-2 parts of carbon nano tube, adding 20-25 parts of diisocyanate, stirring, foaming and curing to obtain the modified lignin polyurethane adsorbent, wherein when the adsorbent is compressed and deformed by 75%, the compression strength is 0.05-5Mpa, and the number of circulations is more than 100; the porosity is 75% -95%; the adsorption efficiency of the heavy oil is 5.2-12.6g/g, the problem that the adsorption effect of lignin-based adsorption materials on the heavy oil in the prior art is poor is solved, and the adsorption material has good mechanical property, oil absorption capacity and cycle performance, and has stable oil absorption capacity after five cycles.
Description
Technical Field
The invention relates to the technical field of bio-based high polymer materials, in particular to a modified lignin polyurethane adsorbent and a preparation method thereof.
Background
Polyurethane (PU) is an abbreviation for polyurethane, and a high molecular compound having a repeating unit of an amino acid ester bond in the main chain is collectively called polyurethane. Polyurethanes are generally obtained by reacting di-or poly-organic isocyanates with polyether polyols or polyester polyol compounds. PU has been developed for over 80 years and is a high molecular polymer with wide application. It is in the form of many products such as foams, synthetic leathers, rubbers, adhesives, waterproofing materials, fibers, elastomers, coatings, etc. The polyurethane material has excellent performance, wide application and various products, and particularly the polyurethane foam plastic has the most wide application. The polyurethane foam plastic has the advantages of porosity, small relative density and stable chemical property. There are many kinds of polyurethane classification methods, and various polyurethane foams can be classified according to the difference of raw materials, the change of formulation, the difference of preparation method and product characteristics.
Currently, there are three methods for efficiently separating oil and organic solvents from water using oil absorbing materials. The most common method is to use porous materials to absorb oil and organic solvents, which are usually characterized by super-hydrophobic surface, high adsorption rate, low preparation cost, large surface area, etc., and to meet the above characteristics, these porous materials are often prepared by methods of reducing surface energy using organic polymer materials, carbon materials, metal oxides, mineral materials, carbonized materials, etc., or increasing surface roughness using vapor deposition, etching, solid modification, phase separation, or original growth methods, etc.
In addition to the challenge of material preparation, the adsorption of high-viscosity crude oil is the biggest challenge in the field, about 40% of crude oil in the world is high-viscosity crude oil, the adsorption rate of the crude oil is very slow by a conventional adsorption material, and the adsorption is carried out by adopting the light and heat absorption characteristic of a carbon material, increasing the temperature and reducing the viscosity of heavy oil. According to patent CN110204780A, a preparation method of a durable super-hydrophobic polyurethane foam material is disclosed, firstly, polyurethane foam is coarsened; secondly, coarsening the foam to graft silane to obtain functional polyurethane foam; and thirdly, dipping the silane functionalized foam into an organosilane solution for reaction for a period of time, washing and drying to obtain the durable super-hydrophobic polyurethane foam material, so that the preparation of the durable super-hydrophobic polyurethane foam material by recycling waste does not utilize a biomass material (lignin) as a raw material, and does not belong to an environment-friendly adsorbent.
Patent CN109575351A discloses a lignin-based polyurethane foam with excellent elastic function and a preparation method thereof. The method comprises the following steps: preparing lignin-based polyoxyethylene ether by taking lignin as a raw material; mixing lignin polyoxyethylene ether and polyethylene glycol, heating to 60-80 ℃, adding a surfactant, water, an amine catalyst and a tin catalyst, and uniformly mixing; and adding isocyanate, stirring uniformly, and foaming to obtain the lignin-based polyurethane foam with excellent elastic function, so that the problems of low lignin reaction activity, uncontrollable performance and poor rebound resilience of the traditional lignin-based polyurethane foam product are solved, and the lignin-based polyurethane obtained by the method is not applied to the absorption of low-viscosity oil and can not absorb heavy oil.
Disclosure of Invention
The invention aims to overcome the defect that the lignin-based adsorbing material in the prior art has poor heavy oil adsorption effect, mainly researches the preparation of the lignin-based polyurethane adsorbing material, heavy oil adsorption and cycle performance and oil absorption foam, can be successfully prepared by the method, and has better mechanical property, oil absorption capacity and cycle performance and stable oil absorption capacity after five cycles. In addition to this, the material can achieve the lowest impact on the environment through degradation due to the introduction of biomass feedstock (lignin).
In order to achieve the purpose, the invention adopts the technical scheme that:
a preparation method of a modified lignin polyurethane adsorbent comprises the following steps:
(1) according to the weight portion, performing dehydration reaction on 15-45 parts of lignin, 100 parts of polyol and 2.25-6.75 parts of concentrated sulfuric acid to obtain lignin polyol;
(2) according to the weight portion, 25-35 portions of lignin polyol prepared in the step (1) are taken, mixed with 0.2-0.4 portion of catalyst, 0.06-0.12 portion of foaming agent and 0-2 portions of carbon nano tube, stirred and mixed, 20-25 portions of diisocyanate are added, stirred, foamed and cured, and the modified lignin polyurethane adsorbent is obtained.
The biomass product lignin partially replaces petroleum-based polyol, a urethane bond is generated through the reaction of isocyanate and hydroxyl to obtain cross-linked polyurethane, the balance of the generation rate of gel and gas is obtained through the adjustment of a foaming agent and a catalyst, lignin-based polyurethane foam is obtained in the process of generating gas while gelling, and the preparation of the lignin-based polyurethane adsorbent is realized through the photo-thermal effect of a carbon nano tube.
The lignin comprises one or more of alkali lignin, organic solvent lignin, Kraft lignin, lignosulfonate and enzymatic hydrolysis lignin.
The polyalcohol comprises one or more of polyethylene glycol 600, polyethylene glycol 400, polytetrahydrofuran 600, glycerol, ethylene glycol, propylene glycol, pentaerythritol and butanediol.
Preferably, the lignin is organic solvent lignin, the polyol is a mixture of polyethylene glycol 400 and glycerol, and further preferably, the mass ratio of the polyol to the polyethylene glycol 400 to the glycerol is 4: 1. The organic solvent lignin has a complete lignin structure, has high surface hydroxyl content, is easy to modify, has high reaction activity with lignin and isocyanate due to the combination of the polyethylene glycol 400 and the glycerol, and has a molecular weight suitable for preparing the high-resilience lignin-based polyurethane foam.
The reaction temperature of the step (1) is 120-160 ℃, and the time is 0.5-2 hours.
The preferred reaction temperature is 130 ℃ and 150 ℃ and the time is 0.8-1.2 h. The modification degree is low when the reaction temperature is low, and the phenolic hydroxyl group of lignin is not completely reacted. The reaction temperature is high, the polyol has a re-condensation reaction, and lumps appear in the polyol. The modification degree is low when the time is short, and the phenolic hydroxyl group of the lignin is not completely reacted. Over time, a re-coagulation reaction occurs, and lumps appear in the polyol.
Further preferably, the reaction temperature is 140 ℃ and the reaction time is 1 h.
The catalyst comprises one or more of stannous octoate, dibutyltin dilaurate, tetrabutyl titanate, pyridine, triethylamine and triethylene diamine. Organotin-based catalysis is helpful in catalyzing gel reactions and is not conducive to catalyzing gas generation reactions. Tertiary amine catalysts are beneficial for catalyzing gas generating reactions but not for catalyzing gel reactions. The foaming reaction requires a balance of the gel reaction and the gas zencheng rate.
The foaming agent comprises one or more of water, trichloromethane, dichloromethane, n-pentane, acetone and tetrahydrofuran.
Preferably, the catalyst is dibutyltin dilaurate and the blowing agent is water. The reaction of water and isocyanate is very violent, so on the premise of taking green environment-friendly water as a foaming agent, if a tertiary amine catalyst is adopted, a large amount of gas is generated in a foaming reaction before gel is generated, foam grows up firstly, and then the gel is not faded, and dibutyltin dilaurate is adopted as the catalyst, so that the gas generation rate and the gel reaction can reach balance. The diisocyanate comprises any one or the combination of more than two of diphenylmethane diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, p-phenylene diisocyanate, 1, 5-naphthalene diisocyanate, toluene diisocyanate and dicyclohexyl diisocyanate.
In the step (2), the stirring speed before the diisocyanate is added is 300-500r/min, and the stirring speed after the diisocyanate is added is 8000-12000 r/min. The stirring speed is too low, the components cannot be uniformly dispersed, and the reaction is insufficient. The stirring speed is too high, and the friction heat generation of the stirring head influences the reaction process, so that the heat is dispersed unevenly, and the reaction speed is unbalanced.
The invention also provides the modified lignin polyurethane adsorbent obtained by the preparation method, when the modified lignin polyurethane adsorbent is compressed and deformed by 75%, the compression strength is 0.05-5Mpa, and the number of circulations is more than 100; the porosity is 75% -95%; the thermal decomposition starting temperature is 235-265 ℃, and the thermal decomposition final temperature is 450-500 ℃; the adsorption capacity of the heavy oil is 5.2-12.6 g/g.
Compared with the prior art, the invention has the following beneficial effects:
(1) the preparation method of the polyurethane adsorbent is simple and convenient to operate, lignin is used as a raw material, and the obtained adsorption material is good in thermal stability, stable in mechanical property and high in resilience, and can meet the requirement of high adsorption efficiency on heavy oil under actual application conditions.
(2) The lignin-based polyurethane adsorbent obtained by the invention has a very good photo-thermal effect, can absorb sunlight to reduce the viscosity of crude oil, has high adsorption efficiency on heavy oil, overcomes the problem of poor heavy oil adsorption effect of lignin-based polyurethane adsorption materials in the prior art, can be degraded, and reduces the influence degree on the environment.
Drawings
FIG. 1 is a schematic diagram of the synthesis process of the modified lignin polyurethane adsorbent of the present invention.
FIG. 2 is a graph showing the effect of adsorption of heavy oil by the modified lignin polyurethane adsorbent in example 1.
FIG. 3 is a graph of the cyclic compression of the modified lignin polyurethane adsorbent of example 1.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention. Those skilled in the art should understand that they can make modifications and equivalents without departing from the spirit and scope of the present invention, and all such modifications and equivalents are intended to be included within the scope of the present invention.
The synthetic process schematic diagram of the modified lignin polyurethane adsorbent is shown in figure 1, lignin and polyol are subjected to liquefaction reaction under the action of sulfuric acid, and diisocyanate is added to be stirred and foamed to obtain the final polyurethane foaming agent.
Example 1
(1) Respectively weighing 15 parts of enzymatic hydrolysis lignin, 100 parts of polyol (polyethylene glycol 400/glycerol, 80/20) and 2.25 parts of 98% sulfuric acid in parts by weight, placing the mixture in a three-neck flask, mechanically stirring the mixture under the protection of nitrogen, heating the mixture to 140 ℃, reacting the mixture for 1 hour, and removing water to obtain lignin polyol;
respectively weighing 25 parts by weight of lignin-based polyol prepared in the step (1), 0.25 part of dibutyltin dilaurate, 0.08 part of water and 0.15 part of carbon nano tube in a beaker, dispersing and stirring uniformly by ultrasound, adding 20 parts of hexamethylene diisocyanate at a stirring speed of 400r/min, stirring rapidly, pouring into a mold, standing and foaming at room temperature at a stirring speed of 10000r/min, curing, and demolding to obtain the lignin-based polyurethane foam.
Referring to GB/T8813-3When the compression deformation is 75%, the compression rate is 50mm/min, and the cycle number of the cyclic compression test is 100; the porosity measuring method adopts a mercury intrusion instrument IV9500 to measure the porosity; the thermal decomposition starting temperature and the thermal decomposition final temperature are measured by adopting a thermogravimetric analyzer METTLER TOLEDO at a temperature range of 100-800 ℃ and a temperature rise rate of 10 ℃/min under a nitrogen atmosphere.
In a sun light (1.00KW @2) Crude oil adsorption capacity was measured. As shown in FIG. 2, in the absence ofDuring illumination, the adsorption material does not adsorb heavy oil, a large amount of crude oil can be adsorbed within 6 minutes after illumination, crude oil is released after illumination is removed, and the adsorption material can be recycled.
The compressive strength of the foam obtained by the test was 0.05MPa, the cycle efficiency after 100 cycles was 98%, and as shown in FIG. 3, the compressive strength of the material was not substantially changed after 100 cycles. The porosity of the material is 81 percent, the thermal decomposition starting temperature is 246 ℃, and the thermal decomposition final temperature is 495 ℃; the polyurethane has heavy oil adsorption performance, and the crude oil adsorption capacity is 6.40 g/g.
Example 2
The preparation method according to the example 1, wherein 15 parts of the enzymatic hydrolysis lignin is replaced by 30 parts of the enzymatic hydrolysis lignin to obtain the lignin-based polyurethane foam, and the performance tests of the same method show that the compressive strength is 0.08MPa, the cycle efficiency after 100 cycles is 98.75%, the porosity is 83%, the thermal decomposition starting temperature is 253 ℃, and the thermal decomposition final temperature is 500 ℃; the polyurethane has heavy oil adsorption performance, and the crude oil adsorption capacity is 6.27 g/g.
Example 3
The preparation method according to example 1, in which 15 parts of enzymatically hydrolyzed lignin was replaced with 45 parts of enzymatically hydrolyzed lignin, yielded a lignin-based polyurethane foam having characteristics of hardness and friability, which may be due to an excessive amount of lignin as a crosslinking point. The performances of the material are tested by the same method, the compressive strength is more than 2MPa, the material is crushed after deformation of 75 percent, the porosity is 60 percent, the thermal decomposition initial temperature is 258 ℃, and the thermal decomposition final temperature is 512 ℃.
Example 4
The procedure is as in example 1, replacing 0.25 part of dibutyltin dilaurate by 0.5 part of dibutyltin dilaurate. During the foaming reaction, the rate of the gelling reaction is significantly faster than the rate of gas generation, and the resulting foam has large cells and a rigid and brittle foam.
Example 5
The preparation process of example 1 was followed, wherein 0.08 parts of water was replaced by 0.1 parts of water as blowing agent. During the foaming reaction, water reacts with isocyanate to form polyurea, and the amount of water determines the amount of gas generated during the foam forming process, the amount of water increases, the amount of gas generated increases, the foam cells are large, and the foam matrix has uneven color due to the color difference between polyurethane and polyurea.
Example 6
The preparation process according to example 1 was followed in which the rotation speed of 10000r/min was replaced by 8000r/min, and the reaction was started at a low rotation speed when the dispersion of the raw materials became difficult to be uniform, so that the resulting foam was not uniform, and there were places where solid foam was generated, and there were places where viscous liquid state was generated, and it was not a foam material having a stable shape.
Comparative example 1
The preparation method according to example 1, in which water was replaced with chloroform, during the reaction, the viscosity of the mixed liquid of polyol and isocyanate started to rise at an early stage, the temperature was slowly raised, but the boiling point of chloroform was not reached, so the gel reaction was faster than the gas generation rate, and during the preparation of the sample, the sample was first changed from a liquid state to a solid state, and then a large amount of gas was generated, but the shape of the sample was not changed.
Comparative example 2
The preparation according to example 1, in which dibutyltin dilaurate was replaced by triethylenediamine, generated a large amount of gas without gelation during the reaction, and the sample volume rapidly increased, followed by gas evolution and foam collapse. The remaining mass then exothermically and changes from a viscous liquid to a solid, hard and brittle.
Claims (9)
1. The preparation method of the modified lignin polyurethane adsorbent is characterized by comprising the following steps:
(1) according to the weight portion, 15-45 parts of lignin, 100 parts of polyalcohol and 2.25-6.75 parts of concentrated sulfuric acid are subjected to liquefaction reaction to obtain lignin polyalcohol;
(2) according to the weight portion, 25-35 portions of lignin polyol prepared in the step (1) are taken, mixed with 0.2-0.4 portion of catalyst, 0.06-0.12 portion of foaming agent and 0-2 portions of carbon nano tube, stirred and mixed, 20-25 portions of diisocyanate are added, stirred, foamed and cured, and the modified lignin polyurethane adsorbent is obtained.
2. The method for preparing the modified lignin polyurethane adsorbent of claim 1, wherein the lignin comprises one or more of alkali lignin, organosolv lignin, Kraft lignin, lignosulfonate, or enzymatic lignin.
3. The preparation method of the modified lignin polyurethane adsorbent of claim 1, wherein the polyol comprises one or more of polyethylene glycol 600, polyethylene glycol 400, polytetrahydrofuran 600, glycerol, ethylene glycol, propylene glycol, pentaerythritol and butanediol.
4. The method for preparing the modified lignin polyurethane adsorbent of claim 1, wherein the reaction temperature in step (1) is 120-160 ℃ and the time is 0.5-2 hours.
5. The method for preparing the modified lignin polyurethane adsorbent of claim 1, wherein the catalyst comprises one or more of stannous octoate, dibutyltin dilaurate, tetrabutyl titanate, pyridine, triethylamine and triethylenediamine.
6. The preparation method of the modified lignin polyurethane adsorbent of claim 1, wherein the foaming agent comprises one or more of water, chloroform, dichloromethane, n-pentane, acetone and tetrahydrofuran.
7. The method of claim 1, wherein the diisocyanate comprises any one or a combination of two or more of diphenylmethane diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, p-phenylene diisocyanate, 1, 5-naphthalene diisocyanate, toluene diisocyanate, and dicyclohexyl diisocyanate.
8. The method for preparing the modified lignin polyurethane adsorbent as claimed in claim 1, wherein in the step (2), the stirring speed before adding the diisocyanate is 300-500r/min, and the stirring speed after adding the diisocyanate is 8000-12000 r/min.
9. The modified lignin polyurethane adsorbent obtained by the preparation method according to any one of claims 1 to 8, wherein when the modified lignin polyurethane adsorbent is compressed and deformed by 75%, the compression strength is 0.05-5Mpa, and the number of circulations is more than 100; the porosity is 75% -95%; the adsorption capacity of the heavy oil is 5.2-12.6 g/g.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114409921A (en) * | 2022-02-22 | 2022-04-29 | 华南农业大学 | Modified lignin polyol and preparation method of polyurethane hot melt adhesive thereof |
| CN114470298A (en) * | 2021-12-21 | 2022-05-13 | 中国科学院宁波材料技术与工程研究所 | Antibacterial nano silver/lignin polyurethane dressing and one-step preparation method thereof |
| CN114957969A (en) * | 2022-04-27 | 2022-08-30 | 哈尔滨工业大学 | Acetylated lignin modification-based polyurethane oil absorption foam and preparation method and application thereof |
| CN116554497A (en) * | 2023-06-08 | 2023-08-08 | 齐鲁工业大学(山东省科学院) | Method for preparing polyalcohol and bio-based polymer material by using lignin |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114470298A (en) * | 2021-12-21 | 2022-05-13 | 中国科学院宁波材料技术与工程研究所 | Antibacterial nano silver/lignin polyurethane dressing and one-step preparation method thereof |
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| CN116554497A (en) * | 2023-06-08 | 2023-08-08 | 齐鲁工业大学(山东省科学院) | Method for preparing polyalcohol and bio-based polymer material by using lignin |
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Application publication date: 20210611 |