CN110054740A - Lignin modification phenolic resin and preparation method thereof and recombinant material - Google Patents
Lignin modification phenolic resin and preparation method thereof and recombinant material Download PDFInfo
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- CN110054740A CN110054740A CN201910294077.7A CN201910294077A CN110054740A CN 110054740 A CN110054740 A CN 110054740A CN 201910294077 A CN201910294077 A CN 201910294077A CN 110054740 A CN110054740 A CN 110054740A
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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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J161/00—Adhesives based on condensation polymers of aldehydes or ketones; Adhesives based on derivatives of such polymers
- C09J161/04—Condensation polymers of aldehydes or ketones with phenols only
- C09J161/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
- C09J161/14—Modified phenol-aldehyde condensates
Abstract
The present invention provides a kind of preparation method of lignin modification phenolic resin, lignin modification phenolic resin and wood-based plate.It the described method comprises the following steps: lignin, phenol, sodium hydroxide and water being added in reaction kettle and stirred evenly, lignin dispersion liquid is obtained；KCl, choline chloride and phenol are added to the container with certain weight ratio, stir to get ionic catalysis liquid；Lignin dispersion liquid and ionic catalysis liquid are transferred in synthesis reactor, reaction obtains modified lignin resin mixed liquor；First formaldehyde is added to modified lignin resin mixed liquor, after carrying out the first reaction, sodium hydroxide and second batch formaldehyde is added, obtains phenol-formaldehyde resin modified intermediate after carrying out the second reaction；By FeCl3、CuCl2And MnCl2It is added to the container with water, stirs to get inorganic compounding dyeing liquor；And phenol-formaldehyde resin modified intermediate is warming up to 83~85 DEG C, when insulation reaction to viscosity reaches 150~170mPa.s, all inorganic compounding dyeing liquors are added and are reacted.Resin discoloration-resistant obtained is good, and glue-joint strength is high.
Description
Technical field
The present invention relates to a kind of lignin modification phenolic resin of resistance to phototropic and preparation methods, and in particular to is urged with ion
Change liquid modified alkali lignin, and substitutes part phenol, while adding inorganic dyeing liquor and preparing the lignin modification of resistance to phototropic phenolic aldehyde
Resin.
Background technique
Lignin, which is three kinds of benzene oxide units, has tridimensional network by what ehter bond and carbon-carbon bond were interconnected to form
Phenols macromolecule, be the natural organic matter for being only second to cellulose.The annual whole world by plant growth can produce hundred billion tons it is wooden
Element, people produce a large amount of lignin as waste, cause the serious waste of resource while using cellulose,
And pollute environment.Meanwhile lignin itself has methoxyl group, a variety of functional groups such as phenolic hydroxyl group and chemical bond, has very strong anti-
Activity is answered, to carry out chemical modification to it, realizes that comprehensive utilization provides possibility.But low industrial lignin respond is wood
The big obstacle of the one of quality modified-reaction, therefore, there is an urgent need to a kind of method of modifying that can improve lignin autoreactivity ability.
106810653 A of CN discloses a kind of method of biorefinery bagasse lignin-base phenolic resin, is assisted by microwave
The three-step approaches such as the degradation of lignin directional catalyzing, the preparation of low temperature revolving removal reaction dissolvent, phenolic resin are helped, using fluorographite
Alkene group assembled heteropoly acid salt class catalyst, 4- ethyl -phenol of the Catalytic lignin selected for high reaction activity, the catalyst cost
Height, reaction process is complicated, is difficult to apply in industrial production.
CN102528892A discloses a kind of bamboo redwood manufacturing method, and reactive dye are added in phenolic resin to bamboo
Material carries out impregnating by pressure dyeing processing, but the acid scarlet, acid blue, the acid yellow dye that use are influenced to be easy to take off by light
Color causes product colour to change.
In order to overcome the lignin modification phenolic resin of the prior art produce present in above-mentioned deficiency, and with the resin
The product COLOR FASTNESS PROBLEM of production, the present invention set about in terms of reducing production cost and against-sunshine color changing, propose a kind of new fast light change
Color lignin modification phenolic resin production method.
Summary of the invention
The technical problem to be solved in the present invention is to provide a kind of preparation method of lignin modification phenolic resin, utilization is specific
The ionic catalysis liquid and composite inorganic dyeing liquor of composition are modified lignin, polymerize and dye, thus to obtain resistance to phototropic,
The excellent lignin modification phenolic resin of adhesive property.
According to an aspect of the present invention, a kind of preparation method of lignin modification phenolic resin, including following step are provided
It is rapid:
It is stirred evenly Step 1: lignin, phenol, sodium hydroxide and water are added in reaction kettle, obtains lignin dispersion
Liquid；
Step 2: KCl, choline chloride and phenol are added to the container with certain weight ratio, stirring to transparent, obtain from
Muonic catalysis liquid；
Step 3: the lignin dispersion liquid and the ionic catalysis liquid are transferred in synthesis reactor, reaction is obtained
Modified lignin resin mixed liquor；
Step 4: first formaldehyde is added to the modified lignin resin mixed liquor, after carrying out the first reaction, hydroxide is added
Sodium and second batch formaldehyde obtain phenol-formaldehyde resin modified intermediate after carrying out the second reaction；
Step 5: by FeCl3、CuCl2And MnCl2It is added to the container, stirs by certain weight ratio and a certain amount of water
To inorganic compounding dyeing liquor；And
Step 6: the phenol-formaldehyde resin modified intermediate is warming up to 83~85 DEG C, insulation reaction to viscosity reaches 150~
When 170mPa.s, all inorganic compounding dyeing liquors are added, the reaction was continued is made the lignin modification phenolic resin.
In step 1, lignin, phenol, sodium hydroxide and water weight ratio be (20~40): (50~90): (2.7~
6.7): (80~120).
In step 2, the weight ratio of KCl, choline chloride and phenol are (10~30): (20~40): (80~120).
In step 3, the weight ratio of the lignin dispersion liquid and the ionic catalysis liquid is (80~120): (7~9).
Synthetic reaction carries out 2~3 hours at 80~85 DEG C.
In step 4, first reaction and second reaction carry out at 55~60 DEG C.Opposite modified lignin resin is mixed
The total weight of liquid is closed, formaldehyde additional amount is 25%~45%, and the weight ratio of first formaldehyde and second batch formaldehyde is (5~9): (1
~5), and the step addition amount of sodium hydroxide is 8%~16%.
In step 5, FeCl3、CuCl2、MnCl2Weight ratio with water is (80~120): (40~80): (10~30):
(800~1400).
According to another aspect of the present invention, a kind of lignin modification phenolic aldehyde tree prepared according to above-mentioned preparation method is provided
Rouge.
According to a further aspect of the invention, the recombinant material closed with above-mentioned modified phenol formaldehyde resin adhesive with pulping waste liquor is provided.
The beneficial effects of the invention are as follows phenol-formaldehyde resin modified prepared in accordance with the method for the present invention is low in cost, quality is steady
Fixed, solidification temperature is low, and resistance to photochromic is good, and glue-joint strength is high, can be widely used for the bonding of various recombinant materials.
Specific embodiment
The preparation method of the lignin modification phenolic resin provided according to the present invention is described in detail below.
(1) decentralized processing of the lignin in reaction solution
Lignin, phenol, sodium hydroxide and water are added in reaction kettle and stirred evenly, lignin dispersion liquid is obtained.This point
Scattered process is preferably stirred at 40~45 DEG C 30 minutes.
Specifically, the weight ratio of lignin, phenol, sodium hydroxide and water is (20~40): (50~90): (2.7~
6.7): (80~120), such as 30:70:4.7:100.
The effect of the decentralized processing step is that lignin is made to scatter as far as possible in alkaline solution, increase phenolic hydroxyl group with
The probability of formaldehyde reaction.
(2) ionic catalysis liquid synthesizes
Three kinds of KCl, choline chloride, phenol raw materials are pressed into (10~30): (20~40): (80~120), such as 20:30:
100 weight ratio is added to the container, and is stirred transparent to get ionic catalysis liquid to reaction solution.Wherein, container is preferably sealing.
Whipping temp is 60 DEG C~65 DEG C.
In this step, eutectic is prepared under conditions of above as mild as a dove using KCl, choline chloride and phenol as raw material
Ionic liquid, and as media processes lignin, so that lignin is degraded, show as connection ether bond rupture, methoxyl group is de-
It removes, the active group phenolic hydroxyl group of macromolecule internal shows reactivity, forms the phenolic structure comprising vacancy.
In above-mentioned ionic liquid, the complex system to form potassium ion, while the proton generated is complexed in potassium ion and phenol
Pyrogentisinic Acid has reacted catalytic action with formaldehyde, thus make to balance the direction movement to polycondensation reaction generation phenolic resin occurs,
The effect of choline chloride is to improve lignin reaction's activity, and the effect of phenol is that complex compound is formed with potassium ion, three's combination
Comprehensive function is that reaction balance is promoted to develop to the direction for forming resin.
(3) ionic catalysis liquid modified lignin resin
The product (i.e. lignin dispersion liquid and ionic catalysis liquid) of step (1) and (2) is transferred in synthesis reactor, instead
It should obtain modified lignin resin mixed liquor.Synthesis reactor is preferably equipped with stirring and condensing unit.Wherein, lignin dispersion liquid and from
Muonic catalysis liquid, weight ratio are preferably (80~120): (7~9), preferably 100:8.
Synthetic reaction can 80 DEG C~85 DEG C at a temperature of, heat preservation 2~3h carry out.
(4) preparation of lignin modification phenolic resin intermediate
First formaldehyde is added in the modified lignin resin mixed liquor obtained to step (3), and after carrying out the first reaction, hydrogen-oxygen is added
Change sodium and second batch formaldehyde, after carrying out the second reaction, obtains phenol-formaldehyde resin modified intermediate.
First reaction and second reaction carry out at 55~60 DEG C.Specifically, the first reaction is at 55~60 DEG C
It is lower to carry out 60 minutes.
Relative to the total weight of modified lignin resin mixed liquor, formaldehyde additional amount is 25%~45%, preferably 35%, hydroxide
The additional amount of sodium is 8%~16%, preferably 12%, and the weight ratio of first formaldehyde and second batch formaldehyde is (5~9): (1~
5), preferably 7:3.
For example, sodium hydroxide and second batch formaldehyde are separately added into, and by both substances preferably in 90~120 minutes
It is added dropwise to complete.
(5) preparation of inorganic compounding dyeing liquor
By FeCl3、CuCl2、MnCl2Three kinds of inorganic raw materials are added to the container by certain weight ratio and a certain amount of water, are stirred
It mixes to obtain inorganic compounding dyeing liquor.
Wherein, FeCl3、CuCl2、MnCl2Weight ratio with water is (80~120): (40~80): (10~30): (800~
1400), preferably 100:60:20:1000, i.e. 5:3:1:50.
Preferably, container is closed.And the whipping process be included in 50 DEG C~55 DEG C under conditions of stir 10 minutes.
(6) preparation of the lignin modification of resistance to phototropic phenolic resin
Phenol-formaldehyde resin modified intermediate made of step (4) is warming up to 83~85 DEG C, preferably insulation reaction 30min,
The inorganic compounding dyeing liquor of Overall Steps (5) is added when viscosity reaches 150~170mPa.s in 25 DEG C of beginning viscosimetrics, continues
The lignin modification of resistance to phototropic phenolic resin is made in reaction, preferably reaction 20min, cooling discharge.
Preferably, in step made above, the shape for the sodium hydrate aqueous solution that sodium hydroxide is 30% with weight ratio
Formula uses.
In the preparation process in accordance with the present invention, using potassium chloride, choline chloride and phenol as raw material in very mild conditions
Eutectic ionic liquid is prepared, as media processes lignin, sends out lignin by multiple actions such as its solvent, catalyst
Raw degradation, shows as connection ether bond rupture, methoxyl group removing, and the active group phenolic hydroxyl group of macromolecule internal shows reaction and lives
Property, form the phenolic structure comprising vacancy.
FeCl3It is yellowish-brown in itself in aqueous solution, while chromogenic reaction can occurs with phenol again, principle is FeCl3Can and
Complex reaction occurs for the substance containing enol structure (- C=C-OH), generates coloring matter.Phenolic hydroxyl group in phenol is exactly enol
Structure.Such as:
6PhOH+FeCl3→H3[Fe(OPh)6] (purple)+3HCl.
Under alkaline condition, lignin graft is changed due to the conjugated structure of phenols after proton translocation, while by
Chromophore pine and cypress aldehyde radical and α carbonyl in lignin, the light wave that these groups generate cause all in visible light region
Solution is mostly in black or brown.
The inorganic composite catalyst agent that the present invention uses is adjusted using potassium, the difference of sodium ion ionic atmosphere by electrostatic interaction
The gather density of control electrification intermediate product reduces phenol adhesiveness, to control phenol xanthan molecule chain crosslinking degree so as to extend
Storage time keeps quality to stablize, and solidification temperature is low, and discoloration-resistant is good, and glue-joint strength is high.
It is had characteristics that using the lignin modification of resistance to phototropic phenolic resin made from method of the invention
Appearance: reddish brown uniform liquid；Solid content: >=40%；Free formaldehyde :≤0.5%；Free-phenol :≤
0.5%.
Meet GB/T14732-2006 " timber industry adhesive ureaformaldehyde, phenolic aldehyde, melamine resin " standard to want
It asks.
70 grams of A4 printing papers are impregnated with the resin, color fastness to light index reaches the " decoration of GB/T15104-2006 after solidification
Single-board-facing artificial plate " requirement of 6 grade standards.
The present invention is further illustrated below with reference to specific embodiment, but the solution of the present invention is without being limited thereto.
Embodiment
Embodiment 1
(1) decentralized processing of the lignin in reaction solution
In a kettle be added 100 kilograms of tap water, 70 kilograms of phenol, 30 kilograms of lignin, 30% sodium hydroxide it is molten
It 4.7 kilograms of liquid, is stirred to react at 40~45 DEG C 30 minutes, obtains lignin dispersion liquid.
(2) ionic catalysis liquid synthesizes
Three kinds of KCl, choline chloride, phenol raw material weight ratio 20:30:100 are added in the container of sealing, 60 DEG C~65
It is stirred under conditions of DEG C transparent to get ionic catalysis liquid to reaction solution.
(3) ionic catalysis liquid modified lignin resin
The product of step (1) and (2) is transferred to the synthetic reaction equipped with stirring and condensing unit with the weight ratio of 100:8
In device, and modified lignin resin mixed liquor is obtained after keeping the temperature 2h under the conditions of being warming up to 80 DEG C~85 DEG C.
(4) preparation of lignin modification phenolic resin intermediate
In the modified lignin resin mixed liquor that step (3) obtains, 80 kilograms of first formaldehyde is added, and (i.e. modified lignin resin is mixed
Close the 24.5% of liquid), 55~60 DEG C are warming up to, is reacted 60 minutes, 20 kilograms of sodium hydroxide solution of independent dropwise addition 30%
(12%) with 60 kilograms of second batch formaldehyde (i.e. the 10.5% of modified lignin resin mixed liquor), rate of addition is controlled, in 90 minutes
Above two substance is added dropwise to complete, phenol-formaldehyde resin modified intermediate is made.
(5) preparation of inorganic compounding dyeing liquor
By FeCl3、CuCl2And MnCl2Three kinds of inorganic raw materials and water are added in the container of sealing with weight ratio 5:3:1:50,
10 minutes are stirred under conditions of 50 DEG C~55 DEG C to get inorganic compounding dyeing liquor is arrived.
(6) lignin modification of resistance to phototropic phenolic resin is produced
Phenol-formaldehyde resin modified intermediate made of step (4) is warming up to 83~85 DEG C, and insulation reaction 30min, 25
DEG C start viscosimetric, when viscosity reaches 150~170mPa.s, be added Overall Steps (5) inorganic compounding dyeing liquor continue it is anti-
20min is answered, lignin modification phenolic resin is made in cooling discharge.
Following feature measurement is carried out to lignin modification phenolic resin made from embodiment 1:
Appearance: reddish brown uniform liquid；Solid content: 42.5%；Free formaldehyde: 0.21%；Free-phenol:
0.31%.
Meet GB/T14732-2006 " timber industry adhesive ureaformaldehyde, phenolic aldehyde, melamine resin " standard to want
It asks.
70 grams of A4 printing papers are impregnated with the resin, color fastness to light index reaches the " decoration of GB/T15104-2006 after solidification
Single-board-facing artificial plate " requirement of 6 grade standards.
500 grams of above-mentioned lignin modification phenolic resin are taken, 10% flour are added, according to 300g/m2Resin added, be applied to
With a thickness of the Eucalyptus veneer surface of 1.7mm, displayed 30 minutes after gluing, by 140 DEG C of temperature, unit pressure 1.5MPa, the time
The glued board that overall thickness is 17mm is hot pressed into according to 1mm/min.According to the requirement of a kind of glued board, according to GB/T17657-
It is 0.92MPa that 2013 " test methods of evaluating the properties of wood-based panels and surface decorated wood-based panels ", which detect glue-joint strength,.
Comparative example 1
Lignin modification phenolic resin is prepared in the same manner as in Example 1, the difference is that in ionic catalysis liquid
It is added without KCl.
Appearance: reddish brown uniform liquid；Solid content: 41.5%；Free formaldehyde: 0.25%；Free-phenol:
0.42%.
Meet GB/T14732-2006 " timber industry adhesive ureaformaldehyde, phenolic aldehyde, melamine resin " standard to want
It asks.
70 grams of A4 printing papers are impregnated with the resin, color fastness to light index reaches the " decoration of GB/T15104-2006 after solidification
Single-board-facing artificial plate " requirement of 6 grade standards.
500 grams of above-mentioned glue are taken, 10% flour are added, according to 300g/m2Resin added, be applied to a thickness of 1.7mm's
Eucalyptus veneer surface is displayed 30 minutes after gluing, and by 140 DEG C of temperature, unit pressure 1.5MPa, the time is according to 1mm/min heat
It is pressed into the glued board that overall thickness is 17mm.According to the requirement of a kind of glued board, according to GB/T17657-2013 " wood-based plate and decorations
Dough figurine makes foliation method for testing performance " " detection glue-joint strength be 0.68MPa.
Comparative example 2
Lignin modification phenolic resin is prepared in the same manner as in Example 1, the difference is that, it is added without inorganic multiple
Close dyeing liquor.
Appearance: reddish brown uniform liquid；Solid content: 41.2%；Free formaldehyde: 0.28%；Free-phenol:
0.35%.
Meet GB/T14732-2006 " timber industry adhesive ureaformaldehyde, phenolic aldehyde, melamine resin " standard to want
It asks.
70 grams of A4 printing papers are impregnated with the resin, color fastness to light index reaches the " decoration of GB/T15104-2006 after solidification
Single-board-facing artificial plate " requirement of 4 grade standards.
500 grams of above-mentioned glue are taken, 10% flour is added, according to the resin added of 300g/m2, are applied to a thickness of 1.7mm's
Eucalyptus veneer surface is displayed 30 minutes after gluing, and by 140 DEG C of temperature, unit pressure 1.5MPa, the time is according to 1mm/min heat
It is pressed into the glued board that overall thickness is 17mm.According to the requirement of a kind of glued board, according to GB/T17657-2013 " wood-based plate and decorations
Dough figurine makes foliation method for testing performance " " detection glue-joint strength be 0.89MPa.
Comparative example 3
Lignin modification phenolic resin is prepared in the same manner as in Example 1, the difference is that, complex staining liquid
The weight ratio that group becomes acid scarlet, acid blue, Indian yellow and sodium chloride is 1:1:1:1.
Appearance: reddish brown uniform liquid；Solid content: 42.5%；Free formaldehyde: 0.21%；Free-phenol:
0.31%.
Meet GB/T14732-2006 " timber industry adhesive ureaformaldehyde, phenolic aldehyde, melamine resin " standard to want
It asks.
70 grams of A4 printing papers are impregnated with the resin, color fastness to light index reaches the " decoration of GB/T15104-2006 after solidification
Single-board-facing artificial plate " requirement of 5 grade standards.
500 grams of above-mentioned glue are taken, 10% flour are added, according to 300g/m2Resin added, be applied to a thickness of 1.7mm's
Eucalyptus veneer surface is displayed 30 minutes after gluing, and by 140 DEG C of temperature, unit pressure 1.5MPa, the time is according to 1mm/min heat
It is pressed into the glued board that overall thickness is 17mm.According to the requirement of a kind of glued board, according to GB/T17657-2013 " wood-based plate and decorations
Dough figurine makes foliation method for testing performance " " detection glue-joint strength be 0.86MPa.
In conjunction with the explanation and practice of the invention disclosed here, the other embodiment of the present invention is for those skilled in the art
It all will be readily apparent and understand.Illustrate and embodiment is regarded only as being exemplary, true scope of the invention and purport are equal
It is defined in the claims.
Claims (10)
1. a kind of preparation method of lignin modification phenolic resin, which comprises the following steps:
It is stirred evenly Step 1: lignin, phenol, sodium hydroxide and water are added in reaction kettle, obtains lignin dispersion liquid；
Step 2: KCl, choline chloride and phenol are added to the container with certain weight ratio, stirring obtains ion and urges to transparent
Change liquid；
Step 3: the lignin dispersion liquid and the ionic catalysis liquid are transferred in synthesis reactor, reaction is modified
Lignin mixed liquor；
Step 4: be added first formaldehyde to the modified lignin resin mixed liquor, after carrying out the first reaction, be added sodium hydroxide and
Second batch formaldehyde obtains phenol-formaldehyde resin modified intermediate after carrying out the second reaction；
Step 5: by FeCl3、CuCl2And MnCl2It is added to the container by certain weight ratio and a certain amount of water, stirs to get nothing
Machine complex staining liquid；And
Step 6: the phenol-formaldehyde resin modified intermediate is warming up to 83~85 DEG C, insulation reaction to viscosity reaches 150~
When 170mPa.s, all inorganic compounding dyeing liquors are added, the reaction was continued is made the lignin modification phenolic resin.
2. preparation method according to claim 1, wherein in step 1, lignin, phenol, sodium hydroxide and water weight
Amount is than being (20~40): (50~90): (2.7~6.7): (80~120).
3. preparation method according to claim 1, in step 2, the weight ratio of KCl, choline chloride and phenol be (10~
30): (20~40): (80~120).
4. preparation method according to claim 1, in step 3, the lignin dispersion liquid and the ionic catalysis liquid
Weight ratio is (80~120): (7~9).
5. preparation method according to claim 1, in step 3, synthetic reaction carries out 2~3 hours at 80~85 DEG C.
6. preparation method according to claim 1, in step 4, first reaction and second reaction are 55~60
It is carried out at DEG C.
7. preparation method according to claim 1, in step 4, the total weight of the relatively described modified lignin resin mixed liquor,
Formaldehyde additional amount is 25%~45%, and addition amount of sodium hydroxide is the 8%~16% of the modified lignin resin mixed liquor weight, and
The weight ratio of first formaldehyde and second batch formaldehyde is (5~9): (1~5).
8. preparation method according to claim 1, in step 5, FeCl3、CuCl2、MnCl2Weight ratio with water is (80
~120): (40~80): (10~30): (800~1400).
9. a kind of lignin modification phenolic resin of preparation method preparation according to any one of claim 1 to 8.
10. a kind of recombinant material is closed with modified phenol formaldehyde resin adhesive with pulping waste liquor according to claim 9.
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| CN111170796A (en) * | 2020-02-22 | 2020-05-19 | 太尔化工（南京）有限公司 | Process for preparing agricultural slow-release nitrogen fertilizer by regenerating powdery amino resin |
| CN112175557A (en) * | 2020-09-24 | 2021-01-05 | 江苏锋芒复合材料科技集团有限公司 | Adhesive for ultra-wide grinding belt |
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| CN111170796A (en) * | 2020-02-22 | 2020-05-19 | 太尔化工（南京）有限公司 | Process for preparing agricultural slow-release nitrogen fertilizer by regenerating powdery amino resin |
| CN111170796B (en) * | 2020-02-22 | 2022-09-16 | 太尔化工（南京）有限公司 | Process for preparing agricultural slow-release nitrogen fertilizer by regenerating powdery amino resin |
| CN112175557A (en) * | 2020-09-24 | 2021-01-05 | 江苏锋芒复合材料科技集团有限公司 | Adhesive for ultra-wide grinding belt |
| CN114454280A (en) * | 2022-02-15 | 2022-05-10 | 浙江农林大学 | Method for adjusting chromatic aberration of wood veneer |
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