CN114957576A - Preparation method and application of lignin-based phenolic resin - Google Patents
Preparation method and application of lignin-based phenolic resin Download PDFInfo
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- CN114957576A CN114957576A CN202210586953.5A CN202210586953A CN114957576A CN 114957576 A CN114957576 A CN 114957576A CN 202210586953 A CN202210586953 A CN 202210586953A CN 114957576 A CN114957576 A CN 114957576A
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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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/28—Chemically modified polycondensates
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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
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
- C08J5/243—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using carbon fibres
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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
- C08K7/00—Use of ingredients characterised by shape
- C08K7/02—Fibres or whiskers
- C08K7/04—Fibres or whiskers inorganic
- C08K7/06—Elements
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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
- C08J2361/00—Characterised by the use of condensation polymers of aldehydes or ketones; Derivatives of such polymers
- C08J2361/04—Condensation polymers of aldehydes or ketones with phenols only
- C08J2361/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
- C08J2361/14—Modified phenol-aldehyde condensates
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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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
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Abstract
The invention discloses a preparation method and application of lignin-based phenolic resin, which comprises the following steps: s1: mixing and reacting catalyst, phenol and lignin, and performing S2: adding formaldehyde into the mixture obtained in the step S1, and then mixing and reacting, S3: performing solid-liquid separation on the mixture obtained in the step S2; the catalyst is formic acid; the temperature of the mixing reaction in the step S1 is 110-130 ℃; in step S1, the mixing reaction time is 1.5-4 h. In the step S1, the mass ratio of the catalyst, phenol and lignin is 2-9: 1.3-4.5: 1, the lignin-based phenolic resin (LPF) synthesized by the method under the formic acid catalysis condition has good catalysis effect, reduces the corrosion to equipment and the environmental pollution, and has simple post-treatment.
Description
Technical Field
The invention relates to the technical field of organic synthesis, in particular to a preparation method and application of lignin-based phenolic resin.
Background
The phenolic resin has the advantages of good heat resistance, adhesion, flame retardance, corrosion resistance, electrical insulation, size stability, simple and convenient synthesis process and low cost, and is mainly applied to the application fields of molding compounds, plywood, friction materials, composite materials and the like. Meanwhile, carbon fiber/phenolic resin based composite materials have been widely used in the fields of aerospace, medical instruments, sporting goods, friction materials and the like due to their good thermal conductivity, excellent mechanical strength and modulus. Due to the shortage of petrochemical resources and environmental pollution in recent years, the substitution of renewable resources for preparing phenolic resins and the expansion of the application fields thereof become more and more important. Lignocellulose biomass is a rich renewable resource on the earth, can be converted into energy fuels and high value-added chemicals, and can obtain various renewable bio-based materials through biological, physical or chemical methods. Lignin is a crosslinked aromatic polymer composed of three different phenylpropane monomers, has a similar crosslinked network structure as phenolic resins, and thus can highly replace petroleum-derived phenols to prepare phenolic resins, which has been considered as an added value mode for lignin applications.
In the related technology, Enzymatic Hydrolysis (EHL) is used as a raw material to prepare the lignin modified phenolic resin, wherein the Enzymatic Hydrolysis (EHL) is obtained from a byproduct of preparing fuel ethanol by fermenting plant straws, better retains functional groups such as phenolic hydroxyl, methoxyl and the like, and can replace petrochemicals such as phenol and the like to be used for synthesizing high polymers. Because the crude lignin has large molecular weight, complex structure and large steric hindrance, the crude lignin is generally modified to obtain more active functional groups and more proper molecular weight before being used for preparing the lignin modified phenolic resin. However, the existing preparation process of preparing the modified phenolic resin by using the modified lignin has the problems of serious corrosion to equipment, poor reaction effect and the like.
Therefore, the development of the preparation method of the lignin-based phenolic resin which has high reaction activity, is easy to recover and can reduce the corrosion to equipment and the pollution to the environment has important significance.
Disclosure of Invention
The present invention is directed to solving at least one of the problems of the prior art. Therefore, the invention provides a preparation method and application of lignin-based phenolic resin.
The preparation method of the lignin-based phenolic resin comprises the following steps:
s1: mixing the catalyst, the phenol and the lignin for reaction,
s2: adding formaldehyde to the mixture obtained in step S1,
s3: performing solid-liquid separation on the mixture obtained in the step S2;
the catalyst is formic acid;
the temperature of the mixing reaction in the step S1 is 110-130 ℃;
in step S1, the mixing reaction time is 1.5-4 h.
In step S1, the mass ratio of the phenol to the lignin of the catalyst is (2-9): 1.3-4.5: 1.
in the method provided by the invention, the mechanism is as follows:
in step S1, under the acidic condition provided by the catalyst, the α -site of the side chain of the lignin unit structure is cleaved to form a carbonium ion, and a nucleophilic substitution reaction occurs at the ortho-para position of phenol. The content of phenolic hydroxyl groups is increased, thereby improving the reactivity of lignin as a phenol substitute.
In step S2, formaldehyde firstly forms a carbocation structure under acidic conditions, then reacts with free phenol with high reactivity to form o-hydroxymethylphenol and p-hydroxymethylphenol, and then reacts with an ortho-para active site of hydroxyl in a lignin molecular structure and carbocation, because phenol is excessive, hydroxymethyl is condensed with the ortho-para active site of phenolic hydroxyl, lignin is connected with a resin molecular chain in a methylene structure in the process, and the steps are repeated to form the phenolic resin oligomer.
In step S3, the lignin-based phenolic resin can automatically realize layering under acidic conditions, specifically, the catalyst formic acid, unreacted phenol and other by-products are upper liquid phase, and the catalyst and the lignin-based phenolic resin can be layered at room temperature, thereby simply realizing separation and recovery of the catalyst. Meanwhile, the recovered formic acid is recycled through rotary evaporation and other modes.
The method for phenolizing lignin provided by the invention has at least the following beneficial effects:
1. the liquefied Phenolated Lignin (PL) obtained in step S1 of the present invention has higher reactivity, the lignin-based phenol-formaldehyde resin (LPF) synthesized by dripping formaldehyde into the mixed solution has the same core group as the ordinary phenol-formaldehyde resin (NR), the chemical shifts at 30.1-30.2 and 35.3-35.4ppm in nuclear magnetic detection correspond to the O-O' and P-O structures of the phenol-formaldehyde resin, respectively, and the intensity and chemical shift of the active sites and inactive sites in the aromatic carbon region are the same.
2. In the traditional technology, the effect of modifying and activating lignin by adopting inorganic strong acid and strong base is obvious, but the environment and equipment are seriously polluted by phenolated lignin catalyzed by the inorganic strong acid and strong base, and the inorganic acid is easily coated by resin after the viscosity of the system is increased due to resin polycondensation in the reaction, and the subsequent resin oxidation is caused; when oxalic acid or the like is used as the catalyst, it is necessary to co-operate with other slave catalysts. The invention liquefies lignin in formic acid/phenol solution, improves the reaction activity by degrading phenolated lignin under the catalysis of formic acid, has better catalytic effect than oxalic acid, avoids the use of solid catalyst, reduces the pollution to the environment, simultaneously uses formic acid as organic strong acid, can not dissolve with the product at the later stage of resin polycondensation, and can be separated by filtration, rotary evaporation and other modes.
3. The Phenolated Lignin (PL) has higher reaction activity, mainly takes para-position and ortho-position grafting as main phenolation, and is beneficial to direct synthesis of phenolic resin.
4. The method effectively solves the problem of resource waste of lignin, reduces the production cost of lignin phenolization, and is beneficial to the multidirectional development of related enterprises such as papermaking, biofuel and the like.
5. Under the conditions of temperature, time and proportioning, the molecular weight of the obtained phenolized lignin is 2009-2490 g/mol, so that the phenolized lignin is high in phenolic hydroxyl group content and low in molecular weight. Reaction conditions lower than the present invention result in insufficient reaction; the reaction conditions higher than the reaction conditions of the invention can cause self-polymerization of lignin, low phenolic hydroxyl content and increased molecular weight, and cause the reduction of phenolization effect, thereby influencing the synthesis of lignin-based phenolic resin.
6. The phenolic resin (LPF) prepared by the invention has the curing peak temperature of 124-130 ℃ which is lower than the curing temperature of 147 ℃ of NR, has high curing efficiency, and can keep the same tensile property and heat resistance as NR.
7. The bending strength of the carbon fiber reinforced lignin-based phenolic resin prepared by the invention is 152-366MPa, the interlaminar shear strength (ILSS) is 10-28MPa, and 83-75% of high residual carbon content is reserved at 800 ℃.
In some embodiments of the invention, in the step S1, the mass percentage of the formic acid is 85-88%.
In some embodiments of the present invention, in step S1, the temperature of the mixing reaction is 115-125 ℃.
In some embodiments of the present invention, in step S1, the mixing reaction time is 2.5 to 3.5 hours.
In some embodiments of the invention, in step S1, the mass ratio of the phenol to the lignin is 1.5 to 4: 1.
in some embodiments of the present invention, in the step S2, the temperature of the mixture is 65 to 75 ℃ when the formaldehyde is added.
In some embodiments of the present invention, in step S2, the temperature of the mixing reaction is 90-100 ℃.
In some embodiments of the present invention, in step S2, the mixing reaction time is 4-5 hours.
In some embodiments of the invention, step S3 further comprises adjusting the pH of the solid phase after the solid-liquid separation.
In some embodiments of the invention, the pH value of the adjusted solid phase is 5-6.
In some embodiments of the invention, the pH adjusting agent of the solid phase comprises one of sodium hydroxide and potassium hydroxide.
At the above pH, the resin is prevented from being oxidized due to excessive pH adjustment.
In some preferred embodiments of the present invention, the pH adjuster is sodium hydroxide having a concentration of 20 to 40%.
In a second aspect, the invention provides a composite material, and the raw material for preparing the composite material comprises the lignin-based phenolic resin.
In some embodiments of the present invention, the raw materials for preparing the composite material further include urotropin and carbon fiber cloth.
In some preferred embodiments of the present invention, the urotropin is urotropin with a mass percentage of 10%.
In some embodiments of the invention, the raw materials for preparing the composite material further comprise a solvent.
In some embodiments of the invention, the solvent comprises at least one of ethanol and acetone.
In some preferred embodiments of the present invention, the volume ratio of the ethanol to the acetone in the solvent is 4: 1.
in the mixed solvent of ethanol and acetone, the ethanol can ensure the dissolving effect of the solvent on the lignin-based resin, and the acetone is added to dissolve a complex lignin structure.
The third aspect of the invention provides a preparation method of the composite material, which comprises the following steps:
a1: mixing the lignin-based phenolic resin and the urotropine and then curing;
a2: and D, coating the cured resin obtained in the step A1 on the carbon fiber cloth and then curing.
In some embodiments of the invention, the solid to liquid ratio of the solvent to the lignin-based phenolic resin is 2.5 ml/g.
In some embodiments of the invention, step a1 further comprises desolventizing after said curing.
In some embodiments of the invention, the temperature of the desolventizing is 50-70 ℃.
In some embodiments of the present invention, the pressure of the desolventizing is-0.6 to 0.7 MPa.
When the desolventizing pressure is too high, the solvent is volatilized too fast, so that the viscosity of the resin is increased and the resin is easy to generate air pockets.
In some embodiments of the invention, step a1 further comprises adding the desolventized lignin-based phenolic resin to a mold.
In some preferred embodiments of the invention, the mold comprises a dumbbell mold.
In some preferred embodiments of the invention, the dumbbell mold has dimensions of 35mm × 2mm × 1 mm.
In some preferred embodiments of the present invention, the curing in step a1 includes a first curing, a second curing, a third curing, and a fourth curing.
The resin viscosity is increased along with the volatilization of the solvent, the solidification in the invention adopts progressive heating, which is beneficial to reducing the resin viscosity, and simultaneously avoids the generation of bubbles due to the fact that the temperature is too high, the solidification reaction is too fast, and the solvent is not easy to volatilize.
In some embodiments of the present invention, in step A1, the curing pressure is 4-5 MPa.
In some embodiments of the present invention, the temperature of the first curing is 75 to 85 ℃.
In some embodiments of the present invention, the time for the first curing is 0.5 to 0.75 h.
In some embodiments of the present invention, the temperature of the second curing is 85 to 95 ℃.
In some embodiments of the present invention, the time for the second curing is 1.5 to 1.75 hours.
In some embodiments of the present invention, the temperature of the third curing is 115-125 ℃.
In some embodiments of the present invention, the time for the third curing is 1 to 1.25 hours.
In some embodiments of the present invention, the temperature of the fourth curing is 145-155 ℃.
In some embodiments of the present invention, the fourth curing time is 1 to 1.25 hours.
In some embodiments of the present invention, in the step A2, the curing pressure is 4 to 5 MPa.
In some embodiments of the invention, in step a2, the carbon fiber cloth has a size of 80mm × 80 mm.
In some embodiments of the invention, in step a2, the carbon fiber cloth has a weight of 12 g.
In some embodiments of the present invention, in step a2, the cured resin is coated on a carbon fiber cloth to obtain a prepreg.
In some preferred embodiments of the present invention, step a2 further comprises stacking prepregs.
In some embodiments of the present invention, step a2 further comprises drying the stacked prepregs.
In some embodiments of the present invention, in the step A2, the drying temperature is 25-35 ℃.
In some embodiments of the present invention, in the step A2, the drying time is 22-26 h.
In some embodiments of the invention, step a2 further comprises removing ethanol by heating after the drying.
In some embodiments of the invention, the temperature for heating to remove ethanol in the step A2 is 60-70 ℃.
In some preferred embodiments of the present invention, the curing in step a2 includes a first curing, a second curing, and a third curing.
In some embodiments of the present invention, the temperature of the first curing is 85 to 95 ℃.
In some embodiments of the present invention, the time for the first curing is 1 to 1.25 hours.
In some embodiments of the present invention, the temperature of the second curing is 120 to 125 ℃.
In some embodiments of the present invention, the time for the second curing is 1 to 1.25 hours.
In some embodiments of the present invention, the temperature of the third curing is 145 to 155 ℃.
In some embodiments of the present invention, the time for the third curing is 4 to 4.25 hours.
In some preferred embodiments of the present invention, step a2 further includes cutting the cured composite material.
In some preferred embodiments of the present invention, in step a2, the size of the cut is 25mm × 5mm × 2 mm.
A third aspect of the invention proposes the use of a composite material as described above in an industrial part.
In some embodiments of the invention, the industrial part comprises one of a flame retardant part, a load bearing part, and a plastic film part.
Detailed Description
The concept and technical effects of the present invention will be clearly and completely described below in conjunction with the embodiments to fully understand the objects, features and effects of the present invention. It is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments, and those skilled in the art can obtain other embodiments without inventive effort based on the embodiments of the present invention, and all embodiments are within the protection scope of the present invention.
Example 1:
the embodiment provides a preparation method of lignin-based phenolic resin, which comprises the following specific steps:
adding lignin (6g) and phenol (24g) into a three-hole bottle, adding 85% formic acid aqueous solution (40mL), stirring and dissolving, stirring the mixed solution at 120 ℃ for 3h, cooling to 70 ℃, dropwise adding 6.35g of formaldehyde into the mixed solution, heating to 95 ℃ to react for 3h, cooling to room temperature, pouring out and recycling formic acid supernatant, titrating residual formic acid to pH 5-6 with 10% sodium hydroxide, and drying at 80 ℃ to obtain 24.3g of 20LPF, wherein the yield is 75%.
Example 2:
the embodiment provides a preparation method of a composite material, which comprises the following specific steps:
A1. 5g of 20LPF obtained in example 1 was dissolved in 25ml of a mixed solvent (ethanol: acetone ═ 4:1), 0.5g of urotropin was added and stirred uniformly, the solvent was removed under vacuum at 60 ℃ and the resulting resin was put into a dumbbell mold (35 mm. times.2 mm. times.1 mm), precured at 80 ℃ for 0.5h, cured at 4MPa at 90 ℃ for 1h, then at 120 ℃ for 1h and finally at 150 ℃ for 1 h. And (4) carrying out tensile property test on the sample bars according to the national standard GB/T1040-2006.
A2. The phenolic resin obtained in step A1 was coated on a carbon fiber cloth (80 mm. times.80 mm, about 12g) to prepare a prepreg. Stacking 10 layers of prepregs, naturally drying at 30 ℃ for 24h, and further heating to 60 ℃ to remove residual ethanol. The composite was made in a vulcanizer using compression molding technology, cured at 90 ℃ for 1h at 4MPa, then cured at 120 ℃ for 1h, and finally cured at 150 ℃ for 4 h. The composite material plate is cut into 60mm multiplied by 15mm multiplied by 2mm, the bending performance test is carried out according to the national standard GB/T1449-2005, and the interlaminar shear strength (ILSS) test is carried out according to the national standard GB/T30969-2014 after the composite material plate is cut into a sample strip of 25mm multiplied by 5mm multiplied by 2 mm.
Example 3:
this example provides a method for preparing a lignin-based phenolic resin, which differs from example 1 in that the mass of lignin is 9g, the mass of phenol is 21g, and other conditions are the same, thus obtaining 30 LPF.
Example 4:
this example provides a method for producing a composite material, and differs from example 2 in that 20LPF in example 2 is replaced by 30LPF, and the other conditions are the same.
Example 5:
this example provides a method for preparing a lignin-based phenolic resin, which differs from example 1 in that the mass of lignin is 12g, the mass of phenol is 18g, and other conditions are the same, thus obtaining 40 LPF.
Example 6:
this example provides a method for producing a composite material, and differs from example 2 in that 20LPF in example 2 is replaced by 40LPF, and the remaining conditions are the same.
Example 7:
this example provides a method for preparing a lignin-based phenolic resin, which differs from example 1 in that the mass of lignin is 15g, the mass of phenol is 15g, and other conditions are the same, thus obtaining 40 LPF.
Example 8:
this example provides a method for preparing a composite material, and the difference between this example and example 2 is that 20LPF was replaced by 50LPF in example 2, and the rest conditions are the same.
Test example 1
This test example 1 was subjected to performance tests on 20LPF, 30LPF, 40LPF and 50LPF, and the test results are shown in table 1.
TABLE 1 LPF Performance testing
The tensile strength of the phenolic resin prepared by the method is 41-70MPa, the Young modulus is 2.49-4.19GPa, and the elongation at break is 3.11-4.03%.
Test example 2
This test example 2 was subjected to performance tests on 20LPF, 30LPF, 40LPF and 50LPF, and the test results are shown in table 2.
Table 1 performance testing of composites
The bending strength of the composite material prepared by the invention is 152-366MPa, and the interlaminar shear strength (ILSS) is 10-28 MPa.
While the embodiments of the present invention have been described in detail, the present invention is not limited to the embodiments, and various changes can be made without departing from the spirit of the present invention within the knowledge of those skilled in the art. Furthermore, the embodiments of the present invention and the features of the embodiments may be combined with each other without conflict.
Claims (10)
1. The preparation method of the lignin-based phenolic resin is characterized by comprising the following steps:
s1: mixing the catalyst, the phenol and the lignin for reaction,
s2: adding formaldehyde into the mixture obtained in the step S1, mixing and reacting,
s3: performing solid-liquid separation on the mixture obtained in the step S2;
the catalyst is formic acid;
the temperature of the mixing reaction in the step S1 is 110-130 ℃;
in the step S1, the mixing reaction time is 1.5-4 h;
in the step S1, the mass ratio of the phenol to the lignin of the catalyst is 2-9: 1.3-4.5: 1.
2. the method for producing a lignin-based phenolic resin according to claim 1, wherein the mixing temperature in step S1 is 115-125 ℃.
3. The method for producing a lignin-based phenolic resin according to claim 1, wherein the temperature of the mixing reaction in step S2 is 90 to 100 ℃.
4. The method for producing a lignin-based phenolic resin according to claim 1, further comprising adjusting the pH of the solid phase after the solid-liquid separation in step S3.
5. The method for producing a lignin-based phenolic resin according to claim 4, wherein in step S3, the pH value after the adjustment is 5 to 6.
6. A composite material, characterized in that the raw material for preparing the composite material comprises the lignin-based phenolic resin obtained by the preparation method of any one of claims 1 to 5.
7. The composite material of claim 6, wherein the raw materials for preparing the composite material further comprise urotropin and carbon fiber cloth.
8. The composite material according to claim 6, wherein the raw material for preparing the composite material further comprises a solvent, preferably the solvent comprises at least one of ethanol and acetone.
9. A method of preparing a composite material according to any one of claims 6 to 8, comprising the steps of:
a1: mixing the lignin-based phenolic resin and the urotropine;
a2: and D, coating the resin obtained in the step A1 on the carbon fiber cloth and then curing.
10. Use of a composite material according to claims 6 to 8 in industrial parts.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB841749A (en) * | 1957-04-16 | 1960-07-20 | Udic Sa Lausanne | Lignin-modified phenolic resins |
| JP2007247123A (en) * | 2006-03-20 | 2007-09-27 | Gun Ei Chem Ind Co Ltd | Method for producing carbon fiber and activated carbon fiber |
| CN102585128A (en) * | 2012-01-21 | 2012-07-18 | 山东圣泉化工股份有限公司 | Preparation method of phenolic resin bonding agents for automobile felts |
| CN104250361A (en) * | 2013-06-26 | 2014-12-31 | 中国科学院化学研究所 | Lignin modified phenolic resin, foam thereof, preparation method of resin, and preparation method of foam |
| CN105431466A (en) * | 2013-06-26 | 2016-03-23 | 植物材料工业公司 | Phenolic resin obtained by polycondensation of formaldehyde, phenol and lignin |
-
2022
- 2022-05-27 CN CN202210586953.5A patent/CN114957576A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB841749A (en) * | 1957-04-16 | 1960-07-20 | Udic Sa Lausanne | Lignin-modified phenolic resins |
| JP2007247123A (en) * | 2006-03-20 | 2007-09-27 | Gun Ei Chem Ind Co Ltd | Method for producing carbon fiber and activated carbon fiber |
| CN102585128A (en) * | 2012-01-21 | 2012-07-18 | 山东圣泉化工股份有限公司 | Preparation method of phenolic resin bonding agents for automobile felts |
| CN104250361A (en) * | 2013-06-26 | 2014-12-31 | 中国科学院化学研究所 | Lignin modified phenolic resin, foam thereof, preparation method of resin, and preparation method of foam |
| CN105431466A (en) * | 2013-06-26 | 2016-03-23 | 植物材料工业公司 | Phenolic resin obtained by polycondensation of formaldehyde, phenol and lignin |
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