CN116478649B - Wood adhesive based on biomass hyperbranched polyol-biomass polyacid, and preparation method and application thereof - Google Patents

Wood adhesive based on biomass hyperbranched polyol-biomass polyacid, and preparation method and application thereof Download PDF

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Publication number
CN116478649B
CN116478649B CN202310006290.XA CN202310006290A CN116478649B CN 116478649 B CN116478649 B CN 116478649B CN 202310006290 A CN202310006290 A CN 202310006290A CN 116478649 B CN116478649 B CN 116478649B
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biomass
anhydride
acid
polyol
hyperbranched polyol
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CN116478649A (en
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张莲鹏
金涛
刘砾
曾贺扬
石森磊
黄跃峰
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Southwest Forestry University
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Southwest Forestry University
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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
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27D—WORKING VENEER OR PLYWOOD
    • B27D1/00—Joining wood veneer with any material; Forming articles thereby; Preparatory processing of surfaces to be joined, e.g. scoring
    • B27D1/04—Joining wood veneer with any material; Forming articles thereby; Preparatory processing of surfaces to be joined, e.g. scoring to produce plywood or articles made therefrom; Plywood sheets
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27D—WORKING VENEER OR PLYWOOD
    • B27D1/00—Joining wood veneer with any material; Forming articles thereby; Preparatory processing of surfaces to be joined, e.g. scoring
    • B27D1/04—Joining wood veneer with any material; Forming articles thereby; Preparatory processing of surfaces to be joined, e.g. scoring to produce plywood or articles made therefrom; Plywood sheets
    • B27D1/08—Manufacture of shaped articles; Presses specially designed therefor
    • 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
    • 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
    • C08G63/123—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
    • C08G63/137—Acids or hydroxy compounds containing cycloaliphatic rings
    • 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
    • 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
    • C08G63/60—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds
    • 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
    • C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
    • C08G83/002—Dendritic macromolecules
    • C08G83/005—Hyperbranched macromolecules
    • 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
    • C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
    • C08G83/002—Dendritic macromolecules
    • C08G83/005—Hyperbranched macromolecules
    • C08G83/006—After treatment of hyperbranched macromolecules
    • 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

Abstract

The invention discloses a preparation method of a biomass hyperbranched polyol-biomass polyacid wood adhesive, which comprises the following steps: (1) preparing a biomass hyperbranched polyol; (2) Mixing the biomass hyperbranched polyol prepared in the step (1) with biomass polybasic acid, and carrying out polycondensation reaction to successfully prepare the wood adhesive; (3) adding a proper amount of aqueous solution to prepare the viscosity. The method effectively solves the problems of formaldehyde free and the like through simple preparation. Can effectively promote the development of biomass industry and provide a novel, green and environment-friendly wood adhesive.

Description

Wood adhesive based on biomass hyperbranched polyol-biomass polyacid, and preparation method and application thereof
Technical Field
The invention belongs to the technical field of macromolecules, and particularly relates to a wood adhesive based on biomass hyperbranched polyol-biomass polyacid, and a preparation method and application thereof.
Background
The artificial board yield in China is about 3 hundred million cubic meters per year. As one of the most widely used materials in our country, artificial boards are widely used in indoor decoration and furniture manufacturing. The adhesive plays a critical role in the wood-based panel industry, and consumes about 1500 ten thousand tons. However, most of the raw materials of the current commercial adhesives are from non-renewable resources, shortage of fossil resources and environmental problems caused by fossil-based products have a great influence on sustainable development of human beings. In addition, formaldehyde release is an unavoidable problem of most adhesives, and has bad influence on human body and environment. Therefore, the development of the sustainable, pollution-free and low-cost biomass adhesive is expected to replace the traditional adhesive to a certain extent.
Disclosure of Invention
The invention aims to provide a biomass adhesive with excellent bonding strength, which utilizes succinic anhydride and xylitol to form hyperbranched polyol and then crosslinks with biomass polybasic acid. The adhesive forms a compact hyperbranched crosslinked network, and is used for improving the bonding strength of the plywood when the adhesive is used for manufacturing the plywood.
The technical scheme of the invention is as follows:
the wood adhesive based on the biomass hyperbranched polyol-biomass polyacid is prepared from hyperbranched polyol and biomass polyacid, wherein the molar ratio of the hyperbranched polyol to the biomass polyacid is as follows: 1:0.6-1, the reaction time is 0.5-2h;
the hyperbranched polyol is prepared from anhydride and biomass polyol.
The invention relates to a preparation method of a biomass hyperbranched polyol-biomass polyacid wood adhesive, which comprises the following steps:
(1) Firstly, mixing succinic anhydride and xylitol (molar ratio 1:1) at room temperature, adding the mixture into a reactor, heating the mixture to 130 ℃ and continuously stirring the mixture for 2 hours to obtain hyperbranched polyol;
(2) Then, mixing hyperbranched polyol and biomass polybasic acid (molar ratio is 1:0.6-1), adding the mixture into a reactor, heating the mixture to 140 ℃, and continuously stirring the mixture for 0.5-2h to obtain a target adhesive;
(3) Finally, cooling the product to room temperature after the reaction is finished, and adding deionized water according to the solid content of 40-60% to completely dissolve the product.
The invention has the advantages that:
the biomass raw material is utilized, so that the problem of volatilization of toxic substances does not exist. Succinic anhydride, also known as succinic anhydride, is produced by dehydration of succinic acid. The natural source of succinic acid is amber, etc. which is obtained by burying resin of Pinus plant under ground for a long time, and is widely found in tissues of various plants and animals. Xylitol is a sweetener extracted from plant materials such as birch, oak, corncob, bagasse, etc., and has a wide distribution range in nature and is widely found in various fruits, vegetables and grains. Citric acid is present in the bones, muscles and blood of plants such as lemon, orange, pineapple and the like and animals, and is rich in reserves. Meanwhile, in the synthesis process of the adhesive, no catalyst is added, and the obtained adhesive has good water solubility.
Drawings
FIG. 1 is a schematic representation of the preparation of the hyperbranched polyol of the invention;
fig. 2 is a schematic illustration of the preparation of a biomass hyperbranched polyol-biomass polyacid-based wood adhesive of the invention.
Detailed Description
In order to better understand the present invention, the following specific examples will be used to describe the technical aspects of the present invention in detail, but the present invention is not limited thereto.
Example 1
The embodiment provides a preparation method of a wood adhesive based on biomass hyperbranched polyol-biomass polyacid, which comprises the following steps:
(1) 10g of succinic anhydride and 15.2g of xylitol are weighed at room temperature, and are mixed and continuously stirred for reaction for 2 hours at 130 ℃;
(2) The hyperbranched polyol prepared above and citric acid (11.52 g) were mixed and reacted at 140℃with continuous stirring for 1 hour;
(3) Cooling to room temperature after the reaction, and adding 16.32g of deionized water to completely dissolve the mixture.
(4) The hot pressing temperature of the plywood is 200 ℃, the hot pressing pressure is 1MPa, and the hot pressing time is 5min.
Example 2
The embodiment provides a preparation method of a wood adhesive based on biomass hyperbranched polyol-biomass polyacid, which comprises the following steps:
(1) 10g of succinic anhydride and 15.2g of xylitol are weighed at room temperature, and are mixed and continuously stirred for reaction for 2 hours at 130 ℃;
(2) The hyperbranched polyol prepared above and itaconic acid (15.36 g) are mixed and continuously stirred at 140 ℃ for reaction for 1 hour;
(3) Cooling to room temperature after the reaction, and adding 18.18g of deionized water to completely dissolve the mixture.
(4) The hot pressing temperature of the plywood is 200 ℃, the hot pressing pressure is 1MPa, and the hot pressing time is 5min.
Example 3
The embodiment provides a preparation method of a wood adhesive based on biomass hyperbranched polyol-biomass polyacid, which comprises the following steps:
(1) 10g of succinic anhydride and 15.2g of xylitol are weighed at room temperature, and are mixed and continuously stirred for reaction for 2 hours at 130 ℃;
(2) The hyperbranched polyol prepared above and citric acid (19.2 g) are mixed and continuously stirred at 140 ℃ for reaction for 1 hour;
(3) Cooling to room temperature after the reaction, and adding 20g of deionized water to completely dissolve the mixture.
(4) The hot pressing temperature of the plywood is 200 ℃, the hot pressing pressure is 1MPa, and the hot pressing time is 5min.
Example 4
The embodiment provides a preparation method of a wood adhesive based on biomass hyperbranched polyol-biomass polyacid, which comprises the following steps:
(1) 10g of succinic anhydride and 15.2g of xylitol are weighed at room temperature, and are mixed and continuously stirred for reaction for 2 hours at 130 ℃;
(2) The hyperbranched polyol prepared above and camphoric acid (19.2 g) were mixed and reacted at 140℃with continuous stirring for 0.5h;
(3) Cooling to room temperature after the reaction, and adding 20g of deionized water to completely dissolve the mixture.
(4) The hot pressing temperature of the plywood is 200 ℃, the hot pressing pressure is 1MPa, and the hot pressing time is 5min.
Example 5
The embodiment provides a preparation method of a wood adhesive based on biomass hyperbranched polyol-biomass polyacid, which comprises the following steps:
(1) 10g of succinic anhydride and 15.2g of xylitol are weighed at room temperature, and are mixed and continuously stirred for reaction for 2 hours at 130 ℃;
(2) The hyperbranched polyol prepared above and succinic acid (19.2 g) were mixed and reacted at 140℃with continuous stirring for 2 hours;
(3) Cooling to room temperature after the reaction, and adding 20g of deionized water to completely dissolve the mixture.
(4) The hot pressing temperature of the plywood is 200 ℃, the hot pressing pressure is 1MPa, and the hot pressing time is 5min.
Example 6
The embodiment provides a preparation method of a wood adhesive based on biomass hyperbranched polyol-biomass polyacid, which comprises the following steps:
(1) 10g of succinic anhydride and 15.2g of xylitol are weighed at room temperature, and are mixed and continuously stirred for reaction for 2 hours at 130 ℃;
(2) The hyperbranched polyol prepared above and camphoric acid (19.2 g) were mixed and reacted at 140℃with continuous stirring for 1 hour;
(3) Cooling to room temperature after the reaction, and adding 20g of deionized water to completely dissolve the mixture.
(4) The hot pressing temperature of the plywood is 210 ℃, the hot pressing pressure is 1MPa, and the hot pressing time is 5min.
Example 7
The embodiment provides a preparation method of a wood adhesive based on biomass hyperbranched polyol-biomass polyacid, which comprises the following steps:
(1) 10g of succinic anhydride and 15.2g of xylitol are weighed at room temperature, and are mixed and continuously stirred for reaction for 2 hours at 130 ℃;
(2) The hyperbranched polyol prepared above and fumaric acid (19.2 g) were mixed and reacted at 140℃with continuous stirring for 1 hour;
(3) Cooling to room temperature after the reaction, and adding 20g of deionized water to completely dissolve the mixture.
(4) The hot pressing temperature of the plywood is 220 ℃, the hot pressing pressure is 1MPa, and the hot pressing time is 5min.
The test of the bonding strength is carried out according to the relevant requirements in the national standard GB/T17657-2013, firstly, the sample is sawed into the same size (100 mm multiplied by 25 mm), slotting is carried out, and the area of the adhesive layer part is 25mm multiplied by 25mm. Respectively soaking the materials in water baths at 63+/-3 ℃ and 93+/-3 ℃ for 3 hours, taking out the materials, standing the materials for ten minutes at normal temperature, and then using an electronic universal mechanical tester for glue strength test. The test results are shown in Table 1:
table 1 properties of plywood made with different adhesives
Group number Dry shear strength/MPa 3h Hot Water (63 ℃ C.) soaking Wet Strength/MPa Soaking wet strength/MPa in boiling water (93 ℃ C.) for 3h
Example 1 1.91 1.14 1.21
Example 2 2.11 1.09 1.28
Example 3 1.97 1.34 1.35
Example 4 2.23 1.06 1.17
Example 5 2.07 1.39 1.37
Example 6 2.03 1.42 1.48
Example 7 2.14 1.59 1.53
The above examples are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above examples. Any other substitutions, modifications, combinations, and simplifications, which do not depart from the spirit and principles of the invention, are intended to be included within the scope of the invention.

Claims (4)

1. A wood adhesive based on biomass hyperbranched polyol-biomass polyacid is characterized in that: the preparation method is characterized by comprising the steps of preparing hyperbranched polyol and biomass polybasic acid, wherein the molar ratio of the hyperbranched polyol to the biomass polybasic acid is as follows: 1:0.6-1, the reaction time is 0.5-2h;
the hyperbranched polyol is prepared from anhydride and biomass polyol;
the anhydride is any one of maleic anhydride, succinic anhydride, phthalic anhydride, methyltetrahydrophthalic anhydride, trimellitic anhydride, chlorendic anhydride, tetrabromophthalic anhydride and tetrachloro-benzene dicarboxylic anhydride;
the biomass polyol is any one of glycerol, erythritol, xylitol, mannitol, sorbitol and maltitol;
the biomass polybasic acid is any one of oxalic acid, fumaric acid, succinic acid, itaconic acid, glutamic acid, malic acid, tartaric acid, camphoric acid and citric acid;
the wood adhesive is prepared by the following preparation method:
(1) Mixing anhydride and biomass polyol according to a molar ratio of 1:1 at room temperature, adding the mixture into a reactor, and continuously stirring the mixture for 2 hours at the temperature of 130 ℃ to obtain hyperbranched polyol;
(2) Mixing the hyperbranched polyol obtained in the step (1) with biomass polybasic acid according to the molar ratio of 1:0.6-1, and placing the mixture in a reactor for reaction for 0.5-2h;
(3) After the reaction is finished, the product is cooled to room temperature, and deionized water is added according to the solid content of 40-60% to completely dissolve the product.
2. A method of preparing the wood adhesive of claim 1, comprising the steps of:
(1) Mixing anhydride and biomass polyol according to a molar ratio of 1:1 at room temperature, adding the mixture into a reactor, and continuously stirring the mixture for 2 hours at the temperature of 130 ℃ to obtain hyperbranched polyol;
(2) Mixing the hyperbranched polyol obtained in the step (1) with biomass polybasic acid according to the molar ratio of 1:0.6-1, and placing the mixture in a reactor for reaction for 0.5-2h;
(3) After the reaction is finished, the product is cooled to room temperature, and deionized water is added according to the solid content of 40-60% to completely dissolve the product.
3. The method for preparing the wood adhesive according to claim 2, wherein the acid anhydride is succinic anhydride;
the biomass polyol is xylitol;
the biomass polybasic acid is citric acid.
4. A three-ply plywood characterized by comprising the steps of:
and A, drying: drying the poplar veneer until the water content is lower than 9%;
b, sizing: double-sided gluing with the adhesive according to any one of claims 1 to 3, with a single-sided gluing quantity of 150g/m 2 No aging is required;
c, blank assembly: based on vertical texture mode
D, hot pressing: the hot pressing temperature is 200-220 ℃, the hot pressing pressure is 1MPa, and the hot pressing time is 5min.
CN202310006290.XA 2023-01-04 2023-01-04 Wood adhesive based on biomass hyperbranched polyol-biomass polyacid, and preparation method and application thereof Active CN116478649B (en)

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997002138A1 (en) * 1995-06-30 1997-01-23 Eastman Chemical Company Method of bonding wood materials using a copolyester
US5698061A (en) * 1993-12-16 1997-12-16 Eastman Chemical Company Method of bonding wood materials using a copolyester
CN103320078A (en) * 2013-05-23 2013-09-25 济南大学 Plant-based polyester polyol-chitosan adhesive, and preparation method and application thereof
FR2995549A1 (en) * 2012-09-19 2014-03-21 Arc Nucleart Method for treating substrate in wood material utilized for e.g. door, involves performing heat treatment for esterification of glycerol and citric acid, where material includes wood brought upto temperature between specific ranges
CN108641673A (en) * 2018-05-10 2018-10-12 北京盛大华源科技有限公司 A kind of preparation method of plywood without formaldehyde release
CN112831036A (en) * 2020-12-30 2021-05-25 中国林业科学研究院林业新技术研究所 Plant glycosyl polyester adhesive as well as preparation method and application thereof
CN114517072A (en) * 2022-03-10 2022-05-20 天津元汇科技有限公司 Water-soluble degradable biomass hyperbranched citric acid polyester adhesive and application thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130324644A1 (en) * 2012-05-31 2013-12-05 Bioamber Inc. Bio-derived polyester for use in composite panels, composite articles and methods of producing such articles

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5698061A (en) * 1993-12-16 1997-12-16 Eastman Chemical Company Method of bonding wood materials using a copolyester
WO1997002138A1 (en) * 1995-06-30 1997-01-23 Eastman Chemical Company Method of bonding wood materials using a copolyester
FR2995549A1 (en) * 2012-09-19 2014-03-21 Arc Nucleart Method for treating substrate in wood material utilized for e.g. door, involves performing heat treatment for esterification of glycerol and citric acid, where material includes wood brought upto temperature between specific ranges
CN103320078A (en) * 2013-05-23 2013-09-25 济南大学 Plant-based polyester polyol-chitosan adhesive, and preparation method and application thereof
CN108641673A (en) * 2018-05-10 2018-10-12 北京盛大华源科技有限公司 A kind of preparation method of plywood without formaldehyde release
CN112831036A (en) * 2020-12-30 2021-05-25 中国林业科学研究院林业新技术研究所 Plant glycosyl polyester adhesive as well as preparation method and application thereof
CN114517072A (en) * 2022-03-10 2022-05-20 天津元汇科技有限公司 Water-soluble degradable biomass hyperbranched citric acid polyester adhesive and application thereof

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