CN117801750A - Preparation and use method of formaldehyde-free synthetic resin adhesive - Google Patents
Preparation and use method of formaldehyde-free synthetic resin adhesive Download PDFInfo
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- CN117801750A CN117801750A CN202310573397.2A CN202310573397A CN117801750A CN 117801750 A CN117801750 A CN 117801750A CN 202310573397 A CN202310573397 A CN 202310573397A CN 117801750 A CN117801750 A CN 117801750A
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- Prior art keywords
- resin adhesive
- tannic acid
- synthetic resin
- glucose
- maleic anhydride
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- Granted
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- 239000000853 adhesive Substances 0.000 title claims abstract description 54
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 54
- 229920003002 synthetic resin Polymers 0.000 title claims abstract description 24
- 239000000057 synthetic resin Substances 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims abstract description 27
- 239000008103 glucose Substances 0.000 claims abstract description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 27
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000001263 FEMA 3042 Substances 0.000 claims abstract description 25
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 claims abstract description 25
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 claims abstract description 25
- 229940033123 tannic acid Drugs 0.000 claims abstract description 25
- 235000015523 tannic acid Nutrition 0.000 claims abstract description 25
- 229920002258 tannic acid Polymers 0.000 claims abstract description 25
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 238000007731 hot pressing Methods 0.000 claims abstract description 8
- 229920005989 resin Polymers 0.000 claims abstract description 6
- 239000011347 resin Substances 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 5
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims abstract description 4
- 238000012673 precipitation polymerization Methods 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 20
- 229920006026 co-polymeric resin Polymers 0.000 claims description 16
- 239000008367 deionised water Substances 0.000 claims description 12
- 229910021641 deionized water Inorganic materials 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 8
- 239000011120 plywood Substances 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 6
- 239000003381 stabilizer Substances 0.000 claims description 5
- 239000003292 glue Substances 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- 238000002791 soaking Methods 0.000 claims 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract description 3
- 238000004513 sizing Methods 0.000 abstract description 3
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- 239000000376 reactant Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000002028 Biomass Substances 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- 241000219000 Populus Species 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- -1 glucose modified melamine-formaldehyde Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
Classifications
-
- 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
- C09J167/00—Adhesives based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Adhesives based on derivatives of such polymers
- C09J167/06—Unsaturated polyesters having carbon-to-carbon unsaturation
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- C08G63/56—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds other than from esters thereof
- C08G63/58—Cyclic ethers; Cyclic carbonates; Cyclic sulfites ; Cyclic orthoesters
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention discloses a preparation and use method of formaldehyde-free synthetic resin adhesive, which comprises the following preparation raw materials: tannic acid, maleic anhydride and glucose, wherein the tannic acid and the maleic anhydride are subjected to precipitation polymerization reaction, and then glucose is added into the reaction product to carry out copolycondensation in water to prepare the resin. The synthetic resin adhesive is used for adhesion, the synthetic resin adhesive is subjected to double-sided sizing for 320g/m < 2 >, the hot pressing temperature is 200 ℃, the pressure is 1.0MPa, and the hot pressing time is 6 minutes. Compared with the prior art, the adhesive is free from formaldehyde, and has good binding force, water resistance and stable color.
Description
Technical Field
The invention discloses a preparation and use method of a formaldehyde-free synthetic resin adhesive, and relates to the technical field of synthetic resin adhesives.
Background
In order to reduce environmental pollution and protect human health, related field personnel are beginning to develop green environment-friendly adhesive. Researchers have found that glucose, which can be made by hydrolyzing starch or cellulose, is a renewable biomass material. Tannic acid is a water extract of plants, which belongs to the natural plant ingredients. The raw materials of the invention are widely available, cheap and easy to obtain, and provide advantages for the environment-friendly biomass adhesive.
In the prior art, patent CN108587539A discloses a preparation method of a glucose modified melamine-formaldehyde resin wood adhesive, which is prepared by taking glucose, melamine and formaldehyde as raw materials and adding a stabilizer, and carrying out methylation and polycondensation reaction. Patent CN101974301a discloses a preparation method of biomass oil-phenol-formaldehyde copolycondensation resin wood adhesive. The invention firstly refines and purifies biomass oil, and then sulfur, alkali catalyst and urea are added to prepare the adhesive with the substitution rate of 60-75%.
The prior art still needs to add formaldehyde to participate in copolycondensation, and can not avoid the problem of releasing formaldehyde, so how to prepare an adhesive without applying formaldehyde is a problem to be solved.
Summary of the invention
The invention aims to provide a preparation and use method of a formaldehyde-free synthetic resin adhesive, and aims to prepare an adhesive which does not apply formaldehyde at all.
In order to achieve the technical purpose and the technical effect, the invention is realized by the following technical scheme:
a preparation and use method of formaldehyde-free synthetic resin adhesive comprises the following raw materials: tannic acid, maleic anhydride and glucose, wherein the tannic acid and the maleic anhydride are subjected to precipitation polymerization reaction, and then glucose is added into the reaction product to carry out copolycondensation in water to prepare the resin.
Further, the preparation steps specifically include:
step 1, tannic acid reacts with maleic anhydride at 90 ℃, and the tannic acid reacts with the maleic anhydride at 90 ℃ for 5-9 hours.
And 2, adding glucose for mixing reaction after the step 1 is completed, adding a stabilizer, and finally obtaining the glucose-tannic acid-maleic anhydride copolymer resin adhesive.
Further, the mass ratio of the glucose to the tannic acid is 1:1, wherein the mole ratio of maleic anhydride to tannic acid is 30:1, the theoretical solid content of the resin is 50-80% after the stabilizer is added.
Further, the step 1 specifically includes: adding 3.4g of tannic acid and 5.88g of maleic anhydride, and placing the mixture in a stirrer at 90 ℃ for reaction for 8 hours;
molar ratio: tannic acid: maleic anhydride 10:300.
further, the step 2 specifically includes: adding 3.4g of glucose into a reactor, and adding deionized water according to the solid content of 60% to uniformly mix the glucose and the deionized water;
mass ratio: glucose: tannic acid is 1:1.
further, the step further includes step 3: and (3) continuously placing the mixture in the step (2) in a stirrer at 90 ℃ for reaction for 6 hours, and cooling to room temperature to obtain the prepared glucose-tannic acid-maleic anhydride copolymer resin adhesive.
The invention further aims to disclose a using method of the formaldehyde-free synthetic resin adhesive, wherein the synthetic resin adhesive is used for adhesion, the synthetic resin adhesive is subjected to double-sided sizing of 320g/m < 2 >, the hot pressing temperature is 200 ℃, the pressure is 1.0MPa, and the hot pressing time is 6 minutes.
Furthermore, the synthetic resin adhesive is used for plywood, the dry shearing strength of the bonding plate is more than or equal to 1.5MPa, the wet strength of the bonding plate after being soaked in water at 63+/-3 ℃ for 3 hours is more than or equal to 1.1MPa, the wet strength of the bonding plate after being boiled in water for 3 hours is more than or equal to 0.9MPa, the bonding plate is more than or equal to the standard requirement of glue for class II plywood with the bonding strength of more than or equal to 0.70MPa in national standard GB/T98462015, and the soaked samples have no glue opening phenomenon.
The beneficial effects are that:
compared with the prior art, the adhesive is free from formaldehyde, and has good binding force, water resistance and stable color.
Of course, it is not necessary for any one product to practice the invention to achieve all of the advantages set forth above at the same time.
Detailed Description
In order to more clearly describe the technical scheme of the embodiment of the present invention, the embodiment will be described in detail.
Example 1
The invention relates to a preparation method of a glucose-tannic acid-maleic anhydride copolymer resin adhesive, which comprises the following steps:
step 1, adding reactants of 1.7g of tannic acid and 2.94g of maleic anhydride into a reactor, and placing the reactants into a stirrer at 90 ℃ for reaction for 8 hours;
step 2, further adding 1.7g of glucose into the reactor, and adding deionized water according to the solid content of 60%, so that the glucose and the deionized water are uniformly mixed;
and 3, continuously placing the mixture in a stirrer at 90 ℃ for reaction for 6 hours, and cooling the mixture to room temperature to obtain the prepared glucose-tannic acid-maleic anhydride copolymer resin adhesive.
Example 2
The invention relates to a preparation method of a glucose-tannic acid-maleic anhydride copolymer resin adhesive, which comprises the following steps:
step 1, adding 8.5g of tannic acid reactant and 14.7g of maleic anhydride reactant into a reactor, and placing the mixture into a stirrer at 90 ℃ for reaction for 8 hours;
step 2, adding 8.5g of glucose into a reactor, and adding deionized water according to the solid content of 50% to uniformly mix the glucose and the deionized water;
and 3, continuously placing the mixture in a stirrer at 90 ℃ for reaction for 6 hours, and cooling the mixture to room temperature to obtain the prepared glucose-tannic acid-maleic anhydride copolymer resin adhesive.
Example 3
The invention relates to a preparation method of a glucose-tannic acid-maleic anhydride copolymer resin adhesive, which comprises the following steps:
step 1, adding reactants of 6.8g of tannic acid and 11.76g of maleic anhydride into a reactor, and placing the mixture into a stirrer at 90 ℃ for reaction for 8 hours;
step 2, adding 6.8g of glucose into a reactor, and adding deionized water according to the solid content of 70% to uniformly mix the glucose and the deionized water;
and 3, continuously placing the mixture in a stirrer at 90 ℃ for reaction for 6 hours, and cooling the mixture to room temperature to obtain the prepared glucose-tannic acid-maleic anhydride copolymer resin adhesive.
Example 4
The invention relates to a preparation method of a glucose-tannic acid-maleic anhydride copolymer resin adhesive, which comprises the following steps:
step 1, adding reactants of 5.1g of tannic acid and 8.82g of maleic anhydride into a reactor, and placing the mixture into a stirrer at 90 ℃ for reaction for 8 hours;
step 2, further adding 5.1g of glucose into a reactor, and adding deionized water according to the solid content of 80% to uniformly mix the glucose and the deionized water;
and 3, continuously placing the mixture in a stirrer at 90 ℃ for reaction for 6 hours, and cooling the mixture to room temperature to obtain the prepared glucose-tannic acid-maleic anhydride copolymer resin adhesive.
Example 5
In connection with the specific implementations described in examples 1-4, to verify the performance characteristics of the synthetic glucose-tannic acid-maleic anhydride copolymer resin adhesive, the following tests were performed:
the glucose-tannic acid-maleic anhydride copolymer resin adhesive prepared in the embodiment is used for pressing a three-layer plywood by using a poplar veneer with the thickness of 2mm, and the physical and mechanical properties of the board are tested according to the requirements of national standard GB/T17657-2013 method for testing the physical and chemical properties of artificial boards and veneer artificial boards, and the water resistance of the board is mainly tested. The method comprises the following specific steps: the synthesized glucose-tannic acid-maleic anhydride copolymer resin adhesive is applied according to the sizing amount of 320g/m 2 The double-sided glue is applied to a single-layer poplar board, the hot pressing temperature is 200 ℃, the hot pressing is carried out for 6 minutes, then the board is cut into 36 test pieces, the dry strength and the wet strength of the board are respectively tested in 3 parts (the test pieces are soaked in water at 63 ℃ for 3 hours), the water resistance (the test pieces are soaked in boiling water for 3 hours) and the like, and the test results are shown in the following table:
table 1 results of adhesive bonding performance test for different reaction conditions:
according to the water resistance requirement of GB/T9846-2015 common plywood on plywood, the performance data of the glucose-tannic acid-maleic anhydride copolymer resin adhesive disclosed by the invention is higher than the national standard requirement.
The above is only an example portion of the application and is not intended to limit the application in any way. Any simple modification, equivalent variation and modification of the above embodiments still fall within the scope of the protection of the technical solution of this application.
Claims (8)
1. The preparation method of the formaldehyde-free synthetic resin adhesive is characterized by comprising the following raw materials: tannic acid, maleic anhydride, and glucose;
and (3) carrying out precipitation polymerization reaction on the tannic acid and the maleic anhydride, and then adding glucose into water for copolycondensation to prepare the resin.
2. The method for preparing formaldehyde-free synthetic resin adhesive according to claim 1, wherein the preparing step specifically comprises:
step 1, tannic acid reacts with maleic anhydride at 90 ℃, and the tannic acid reacts with the maleic anhydride at 90 ℃ for 5-9 hours;
and 2, adding glucose for mixing reaction after the step 1 is completed, adding a stabilizer, and finally obtaining the glucose-tannic acid-maleic anhydride copolymer resin adhesive.
3. The method for preparing formaldehyde-free synthetic resin adhesive according to claim 2, wherein the mass ratio of glucose to tannic acid is 1:1, wherein the mole ratio of maleic anhydride to tannic acid is 30:1, the theoretical solid content of the resin is 50-80% after the stabilizer is added.
4. The method for preparing formaldehyde-free synthetic resin adhesive according to claim 3, wherein the step 1 specifically comprises: adding 3.4g of tannic acid and 5.88g of maleic anhydride, and placing the mixture in a stirrer at 90 ℃ for reaction for 8 hours;
molar ratio: tannic acid: maleic anhydride 10:300.
5. the method for preparing formaldehyde-free synthetic resin adhesive according to claim 3, wherein the step 2 specifically comprises: adding 3.4g of glucose into a reactor, and adding deionized water according to the solid content of 60% to uniformly mix the glucose and the deionized water;
mass ratio: glucose: tannic acid is 1:1.
6. the method for preparing a formaldehyde-free synthetic resin adhesive according to claim 4 or 5, wherein the steps further comprise step 3: and (3) continuously placing the mixture in the step (2) in a stirrer at 90 ℃ for reaction for 6 hours, and cooling to room temperature to obtain the prepared glucose-tannic acid-maleic anhydride copolymer resin adhesive.
7. The method of using a formaldehyde-free synthetic resin adhesive according to any one of claims 1 to 6, wherein the synthetic resin adhesive is used for adhesion, the synthetic resin adhesive is applied with a double-sided size of 320g/m2, the hot pressing temperature is 200 ℃, the pressure is 1.0MPa, and the hot pressing time is 6 minutes.
8. The method for using the formaldehyde-free synthetic resin adhesive according to claim 7, wherein the synthetic resin adhesive is used for plywood, the dry shear strength of the adhesive plate is not less than 1.5MPa, the wet strength of the adhesive plate after 3 hours of water soaking at 63+/-3 ℃ is not less than 1.1MPa, the wet strength of the adhesive plate after 3 hours of boiling water boiling is not less than 0.9MPa, the adhesive standard requirement of class II plywood with the adhesive strength of not less than 0.70MPa in national standard GB/T9846 2015 is met, and the immersed sample has no glue opening phenomenon.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310573397.2A CN117801750B (en) | 2023-05-22 | 2023-05-22 | Preparation and use method of formaldehyde-free synthetic resin adhesive |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310573397.2A CN117801750B (en) | 2023-05-22 | 2023-05-22 | Preparation and use method of formaldehyde-free synthetic resin adhesive |
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| Publication Number | Publication Date |
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| CN117801750A true CN117801750A (en) | 2024-04-02 |
| CN117801750B CN117801750B (en) | 2024-08-20 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN118388364A (en) * | 2024-04-25 | 2024-07-26 | 昆明冶金高等专科学校 | Boiling water-resistant adhesive prepared from biomass polyamine, flame retardant and application |
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|---|---|---|---|---|
| GB928451A (en) * | 1958-06-12 | 1963-06-12 | Polygram Casting Co Ltd | Improvements in thermosetting material |
| WO2011042610A1 (en) * | 2009-10-08 | 2011-04-14 | Upm-Kymmene Wood Oy | Bio-adhesive and wood board |
| JP2015160366A (en) * | 2014-02-27 | 2015-09-07 | ホクシン株式会社 | Fiberboard and production method thereof |
| WO2015153617A1 (en) * | 2014-03-31 | 2015-10-08 | E. I. Du Pont De Nemours And Company | Condensed tannin-based foams |
| US20150321958A1 (en) * | 2012-06-29 | 2015-11-12 | Ursa Insulation, S.A. | Formaldehyde-free binder and use for mineral wool insulation products |
| CN113769155A (en) * | 2021-08-12 | 2021-12-10 | 中国人民解放军海军军医大学 | Biological adhesive based on biological engineering protein and preparation method thereof |
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2023
- 2023-05-22 CN CN202310573397.2A patent/CN117801750B/en active Active
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB928451A (en) * | 1958-06-12 | 1963-06-12 | Polygram Casting Co Ltd | Improvements in thermosetting material |
| WO2011042610A1 (en) * | 2009-10-08 | 2011-04-14 | Upm-Kymmene Wood Oy | Bio-adhesive and wood board |
| US20150321958A1 (en) * | 2012-06-29 | 2015-11-12 | Ursa Insulation, S.A. | Formaldehyde-free binder and use for mineral wool insulation products |
| JP2015160366A (en) * | 2014-02-27 | 2015-09-07 | ホクシン株式会社 | Fiberboard and production method thereof |
| WO2015153617A1 (en) * | 2014-03-31 | 2015-10-08 | E. I. Du Pont De Nemours And Company | Condensed tannin-based foams |
| CN113769155A (en) * | 2021-08-12 | 2021-12-10 | 中国人民解放军海军军医大学 | Biological adhesive based on biological engineering protein and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| ZHAO, ZY 等: "Effects of Sulfuric Acid on the Curing Behavior and Bonding Performance of Tannin-Sucrose Adhesive", POLYMERS, vol. 10, no. 6, 30 June 2018 (2018-06-30), pages 1 - 13 * |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN118388364A (en) * | 2024-04-25 | 2024-07-26 | 昆明冶金高等专科学校 | Boiling water-resistant adhesive prepared from biomass polyamine, flame retardant and application |
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