CN118085214B - Preparation method of polyurethane association type thickener - Google Patents
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- CN118085214B CN118085214B CN202410487480.2A CN202410487480A CN118085214B CN 118085214 B CN118085214 B CN 118085214B CN 202410487480 A CN202410487480 A CN 202410487480A CN 118085214 B CN118085214 B CN 118085214B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/288—Compounds containing at least one heteroatom other than oxygen or nitrogen
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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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/43—Thickening agents
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Abstract
The invention discloses a preparation method of a polyurethane associative thickener, and relates to the technical field of thickener preparation. The method comprises the following steps: adding polyethylene glycol into a reaction kettle filled with inert gas, heating the reaction kettle for dehydration, then adding a proper amount of catalyst and diisocyanate, and starting stirring to fully and uniformly mix; heating the reaction kettle for reaction, adding a synergist into the reaction kettle, continuing to perform heat preservation reaction, and vacuum drying the precipitate after the reaction is finished to obtain white solid, namely the polyurethane associated thickener. The invention effectively solves the problem of difficult dispersion caused by excessive viscosity of the thickener, and has wide application scene.
Description
Technical Field
The invention relates to the technical field of thickener preparation, in particular to a preparation method of polyurethane associative thickener.
Background
With the enhancement of environmental protection and health consciousness of people, water-based paint and other paint with low VOC content are unprecedented. However, the main body of the aqueous coating is a mixture of an aqueous dispersion of pigment and an aqueous dispersion of polymer, and when the effective volume of the dispersed phase is less than 55%, the viscosity is substantially close to that of the aqueous dispersion medium, and other auxiliaries are required to increase the emulsion viscosity, so that an aqueous thickener is produced. The thickening agent is a rheological additive, and after the thickening agent is added, the thickening agent can not only thicken the paint, but also endow the paint with excellent mechanical property and physical and chemical stability. The existing thickening agents for the water-based paint mainly comprise four types: an inorganic thickener; a cellulosic thickener; acrylic thickeners and polyurethane associative thickeners.
Polyurethane associative thickeners are typically formed by condensation polymerization of an oligomeric polyol such as polyether, polyester, and the like with a polyisocyanate. The polyurethane associative thickener is prepared by condensation polymerization of diisocyanate and polyethylene glycol and then end capping with long-chain alcohol or amine by adopting the same chemical reaction principle. The diisocyanate and the long-chain alcohol or amine provide an association group part, and the polyethylene glycol chain segment provides a hydrophilic part, so that the water solubility of the polymer is ensured.
The Chinese patent with the publication number of CN102101908B discloses a water-soluble polyurethane associative thickener and application thereof, wherein polyethylene glycol and a surface active substance with a plurality of ethoxy structures as a blocking agent are dehydrated, diisocyanate and a diisocyanate polycondensate as a chain extender are added at one time under the protection of inert gas, and the reaction is carried out in an organic solvent to obtain the water-soluble polyurethane associative thickener with a branched structure, which has strong thickening capability, environmental protection and wide application range. The invention adopts the surface active substances with a plurality of ethoxy structures as the end capping agent for reaction, has larger molecular weight, stable reaction and convenient industrialized production; the diisocyanate and the chain extender are added in a one-time manner, so that uncertainty of products caused by adding water step by step can be avoided.
The Chinese patent with the publication number of CN101096475B discloses a preparation method of a polyurethane thickener, which comprises the steps of putting screened polyethylene glycol into a four-neck flask for vacuum decompression dehydration treatment, introducing nitrogen for oxygen-expelling treatment after dehydration is qualified, adding a catalyst, fully stirring uniformly, dropwise adding an inert solution of diisocyanate at a proper temperature, generating a polyurethane prepolymer through polymerization of a polymer free radical solution, adding a chain extender for chain extension polymerization after the prepolymer is reacted, then adding a blocking agent for hydrophobic modification, and decompressing and desolventizing an inert solvent to obtain the thickener after the polymerization is complete and the content of free isocyanate is lower than the index range.
However, the thickener prepared in the presently disclosed technology has a problem that excessive viscosity at the same concentration and temperature may cause difficulty in dispersion in an aqueous system.
Disclosure of Invention
In view of the problems identified in the background and the deficiencies of the prior art, it is an object of the present invention to provide a process for the preparation of polyurethane associative thickeners.
The aim of the invention is achieved by the following scheme:
the preparation method of the polyurethane associative thickener comprises the following operation steps:
step one: adding 80-120 parts of polyethylene glycol into a reaction kettle filled with inert gas according to parts by mass, heating the reaction kettle to dehydrate for 2-4 hours, then adding a proper amount of catalyst and 2-10 parts of diisocyanate, and starting stirring to fully and uniformly mix;
step two: and (3) heating the reaction kettle for 2-8h, adding 5-12 parts of synergistic agent into the reaction kettle, continuously preserving heat for 4-10h, and vacuum drying the precipitate after the reaction is finished to obtain white solid, namely the polyurethane associative thickener.
Preferably, the polyethylene glycol in the first step has a molecular weight of 300-30000g/mol.
Preferably, the dehydration temperature of the reaction kettle in the first step is 90-120 ℃, and the dehydration is carried out until the water content is not higher than 0.5%.
Preferably, the catalyst in the first step is used in an amount of 0.1 to 0.8wt% based on the total mass of polyethylene glycol and diisocyanate.
Preferably, the catalyst in the first step is at least one of stannous octoate, dibutyl tin dilaurate, dibutyl tin maleate and zinc octoate.
Preferably, the diisocyanate in the step one is at least one selected from isophorone diisocyanate (IPDI), toluene Diisocyanate (TDI), methylcyclohexyl diisocyanate (HTDI), hexamethylene Diisocyanate (HDI), 4 '-diphenylmethane diisocyanate (MDI), 4' -dicyclohexylmethane diisocyanate (HMDI), 2, 6-diisocyanate methylhexanoate (LDI), xylylene Diisocyanate (XDI), tetramethylxylylene diisocyanate (TMXDI) and naphthalene-1, 5 diisocyanate (NDI).
Preferably, the dehydration temperature of the reaction in the first step is 50-120 ℃.
Preferably, the reaction temperature of the reaction kettle in the second step is 60-120 ℃.
Preferably, the preparation method of the synergist in the second step comprises the following steps:
According to the mass parts, 12-24 parts of mercaptoglycerol, 6-10 parts of 1-methyl-5- (ethylene oxide-2-yl) -1H-pyrazole, 200-300 parts of ethanol and 2-5 parts of sodium ethoxide are slowly added into a reaction kettle, nitrogen is introduced, and the temperature is raised to 60-75 ℃ for reaction for 100-130min; adding 2-6 parts of N-vinyl caprolactam, and reacting at 60-75 ℃ for 60-100min; evaporating the ethanol to obtain the synergist.
Compared with the prior art, the invention has the following beneficial effects:
1. the mercapto glycerol reacts with the epoxy compound 1-methyl-5- (oxiran-2-yl) -1H-pyrazole to generate mercapto-epoxy, and the mercapto (SH) in the mercapto glycerol attacks carbon atoms in the epoxy group, resulting in ring opening of the epoxy group. After ring opening, the mercapto group in the mercaptoglycerol can replace one oxygen atom in the epoxy group to form a new thioether bond, so as to form the compound containing the pyrazole ring. The compound has a blocking effect in the polyurethane thickener, and reduces the viscosity under the same condition so as to improve the dispersibility.
2. The mercaptoglycerol and N-vinyl caprolactam undergo a mercapto-vinyl addition reaction to form a compound containing caprolactam groups. This compound helps to enhance the dispersibility and stability of the polyurethane thickener in water systems while the presence of glycerol can still enhance the dispersibility of the molecules in water.
Detailed Description
In view of the shortcomings in the prior art, the inventor of the present invention has long studied and put forward a technical solution of the present invention, and the technical solution, the implementation process and principle thereof will be further explained as follows.
Example 1: the preparation method of the polyurethane associative thickener comprises the following operation steps:
Step one: adding 80g of polyethylene glycol into a reaction kettle filled with inert gas, heating the reaction kettle to dehydrate for 2 hours, then adding a proper amount of catalyst and 2g of diisocyanate, and starting stirring to fully and uniformly mix;
step two: and (3) heating the reaction kettle for reaction for 2 hours, adding 5g of synergist into the kettle, continuing to perform heat preservation reaction for 4 hours, and vacuum drying the precipitate after the reaction is finished to obtain white solid, namely the polyurethane associative thickener.
In the first step, the molecular weight of polyethylene glycol is 2000g/mol.
And in the first step, the dehydration temperature of the reaction kettle is 90 ℃, and the dehydration is carried out until the water content is not higher than 0.5%.
The dosage of the catalyst in the first step is 0.1 weight percent of the total mass of the polyethylene glycol and the diisocyanate.
The catalyst in the first step is stannous octoate.
The diisocyanate in the first step is selected from isophorone diisocyanate (IPDI).
The dehydration temperature of the reaction in the first step is 50 ℃.
And in the second step, the reaction temperature of the reaction kettle is 60 ℃.
The preparation method of the synergist in the second step comprises the following steps:
12g of mercaptoglycerol, 6g of 1-methyl-5- (ethylene oxide-2-yl) -1H-pyrazole, 200g of ethanol and 2g of sodium ethoxide are slowly added into a reaction kettle, nitrogen is introduced, and the temperature is raised to 60 ℃ for reaction for 100min; 2g of N-vinyl caprolactam is added, and the reaction is carried out for 60min at 60 ℃; evaporating the ethanol to obtain the synergist.
Example 2: the preparation method of the polyurethane associative thickener comprises the following operation steps:
Step one: adding 100g of polyethylene glycol into a reaction kettle filled with inert gas, heating the reaction kettle to dehydrate for 3 hours, then adding a proper amount of catalyst and 5g of diisocyanate, and starting stirring to fully and uniformly mix;
Step two: and (3) heating the reaction kettle for reaction for 4 hours, adding 7g of synergist into the reaction kettle, continuously preserving heat for reaction for 6 hours, and vacuum drying the precipitate after the reaction is finished to obtain white solid, namely the polyurethane associative thickener.
The molecular weight of polyethylene glycol in the first step is 4000g/mol.
And in the first step, the dehydration temperature of the reaction kettle is 100 ℃, and the dehydration is carried out until the water content is not higher than 0.5%.
The catalyst in the first step is used in an amount of 0.3wt% of the total mass of the polyethylene glycol and the diisocyanate.
The catalyst in the first step is dibutyl tin dilaurate.
The diisocyanate in the first step is selected from Toluene Diisocyanate (TDI).
The dehydration temperature of the reaction in the first step is 70 ℃.
And in the second step, the reaction temperature of the reaction kettle is 80 ℃.
The preparation method of the synergist in the second step comprises the following steps:
16g of mercaptoglycerol, 8g of 1-methyl-5- (ethylene oxide-2-yl) -1H-pyrazole, 235g of ethanol and 3g of sodium ethoxide are slowly added into a reaction kettle, nitrogen is introduced, and the temperature is raised to 65 ℃ for reaction for 110min; adding 3g N-vinyl caprolactam at 65 ℃ for reaction for 75min; evaporating the ethanol to obtain the synergist.
Example 3: the preparation method of the polyurethane associative thickener comprises the following operation steps:
step one: adding 100g of polyethylene glycol into a reaction kettle filled with inert gas, heating the reaction kettle to dehydrate for 3 hours, then adding a proper amount of catalyst and 4g of diisocyanate, and starting stirring to fully and uniformly mix;
Step two: and (3) heating the reaction kettle for reaction for 4 hours, adding 7g of synergist into the reaction kettle, continuously preserving heat for reaction for 6 hours, and vacuum drying the precipitate after the reaction is finished to obtain white solid, namely the polyurethane associative thickener.
In the first step, the molecular weight of polyethylene glycol is 6000g/mol.
And in the first step, the dehydration temperature of the reaction kettle is 100 ℃, and the dehydration is carried out until the water content is not higher than 0.5%.
The dosage of the catalyst in the first step is 0.6wt% of the total mass of the polyethylene glycol and the diisocyanate.
The catalyst in the first step is dibutyl tin maleate.
The diisocyanate in step one is selected from methylcyclohexyl diisocyanate (HTDI).
The dehydration temperature of the reaction in the first step is 90 ℃.
And in the second step, the reaction temperature of the reaction kettle is 100 ℃.
The preparation method of the synergist in the second step comprises the following steps:
adding 20g of mercaptoglycerol, 8g of 1-methyl-5- (ethylene oxide-2-yl) -1H-pyrazole, 250g of ethanol and 4g of sodium ethoxide into a reaction kettle slowly, introducing nitrogen, heating to 70 ℃, and reacting for 120min; adding 5g N-vinyl caprolactam at 70 ℃ for reacting for 85min; evaporating the ethanol to obtain the synergist.
Example 4: the preparation method of the polyurethane associative thickener comprises the following operation steps:
Step one: 120g of polyethylene glycol is added into a reaction kettle filled with inert gas, the temperature of the reaction kettle is raised for dehydration for 4 hours, then a proper amount of catalyst and 10g of diisocyanate are added, and stirring is started for full and uniform mixing;
step two: and (3) heating the reaction kettle for reaction for 8 hours, adding 12g of synergist into the reaction kettle, continuously carrying out heat preservation reaction for 10 hours, and vacuum drying the precipitate after the reaction is finished to obtain white solid, namely the polyurethane associative thickener.
In the first step, the molecular weight of polyethylene glycol is 8000g/mol.
And in the first step, the dehydration temperature of the reaction kettle is 120 ℃, and the dehydration is carried out until the water content is not higher than 0.5%.
The dosage of the catalyst in the first step is 0.8 weight percent of the total mass of the polyethylene glycol and the diisocyanate.
The catalyst in the first step is zinc octoate.
The diisocyanate in the first step is selected from Hexamethylene Diisocyanate (HDI).
The dehydration temperature of the reaction in the first step is 120 ℃.
And in the second step, the reaction temperature of the reaction kettle is 120 ℃.
The preparation method of the synergist in the second step comprises the following steps:
slowly adding 24g of mercaptoglycerol, 10g of 1-methyl-5- (ethylene oxide-2-yl) -1H-pyrazole, 300g of ethanol and 5g of sodium ethoxide into a reaction kettle, introducing nitrogen, heating to 75 ℃, and reacting for 130min; adding 6g N-vinyl caprolactam at 75 ℃ for reacting for 100min; evaporating the ethanol to obtain the synergist.
Comparative example 1: the preparation method of the polyurethane associative thickener comprises the following operation steps:
Step one: adding 80g of polyethylene glycol into a reaction kettle filled with inert gas, heating the reaction kettle to dehydrate for 2 hours, then adding a proper amount of catalyst and 2g of diisocyanate, and starting stirring to fully and uniformly mix;
step two: and (3) heating the reaction kettle for reaction for 2 hours, adding 5g of synergist into the kettle, continuing to perform heat preservation reaction for 4 hours, and vacuum drying the precipitate after the reaction is finished to obtain white solid, namely the polyurethane associative thickener.
In the first step, the molecular weight of polyethylene glycol is 2000g/mol.
And in the first step, the dehydration temperature of the reaction kettle is 90 ℃, and the dehydration is carried out until the water content is not higher than 0.5%.
The dosage of the catalyst in the first step is 0.1 weight percent of the total mass of the polyethylene glycol and the diisocyanate.
The catalyst in the first step is stannous octoate.
The diisocyanate in the first step is selected from isophorone diisocyanate (IPDI).
The dehydration temperature of the reaction in the first step is 50 ℃.
And in the second step, the reaction temperature of the reaction kettle is 60 ℃.
The preparation method of the synergist in the second step comprises the following steps:
12g of mercaptoglycerol, 200g of ethanol and 2g of sodium ethoxide are slowly added into a reaction kettle, nitrogen is introduced, and the temperature is raised to 60 ℃ for reaction for 100min; adding 2g N-vinyl caprolactam, and reacting at 60 ℃ for 60min; evaporating the ethanol to obtain the synergist.
Comparative example 2: the preparation method of the polyurethane associative thickener comprises the following operation steps:
Step one: adding 80g of polyethylene glycol into a reaction kettle filled with inert gas, heating the reaction kettle to dehydrate for 2 hours, then adding a proper amount of catalyst and 2g of diisocyanate, and starting stirring to fully and uniformly mix;
step two: and (3) heating the reaction kettle for reaction for 2 hours, adding 5g of synergist into the kettle, continuing to perform heat preservation reaction for 4 hours, and vacuum drying the precipitate after the reaction is finished to obtain white solid, namely the polyurethane associative thickener.
In the first step, the molecular weight of polyethylene glycol is 2000g/mol.
And in the first step, the dehydration temperature of the reaction kettle is 90 ℃, and the dehydration is carried out until the water content is not higher than 0.5%.
The dosage of the catalyst in the first step is 0.1 weight percent of the total mass of the polyethylene glycol and the diisocyanate.
The catalyst in the first step is stannous octoate.
The diisocyanate in the first step is selected from isophorone diisocyanate (IPDI).
The dehydration temperature of the reaction in the first step is 50 ℃.
And in the second step, the reaction temperature of the reaction kettle is 60 ℃.
The preparation method of the synergist in the second step comprises the following steps:
12g of mercaptoglycerol, 6g of 1-methyl-5- (ethylene oxide-2-yl) -1H-pyrazole, 200g of ethanol and 2g of sodium ethoxide are slowly added into a reaction kettle, nitrogen is introduced, and the temperature is raised to 60 ℃ for reaction for 160min, thus obtaining the synergist.
Example evaluation:
the polyurethane associative thickeners obtained in the above examples and comparative examples were subjected to a thickening experiment in pure acrylic emulsion, and the specific procedure is as follows:
the polyurethane associative thickener was prepared as a 3% mass solution from a mixed solution of ethylene glycol and distilled water (mass ratio 1:1), and the solution was accelerated by an ultrasonic cleaner to serve as a thickener for pure acrylic emulsion (solid content 50%, viscosity 0.1 pa.s).
100G of the pure acrylic emulsion was taken and added with the polyurethane associative thickener solution described in the example in an amount of 0.1wt% in sequence, and the emulsion was tested for zero shear viscosity by means of a TA-instrument Inc. ARG-2 stress control rheometer (temperature 20-30 ℃ C., shear rate variation range 0-1000 1/s) and the results are shown in Table 1:
table 1: test results for each example and comparative example
As can be seen from the test data of the above examples and comparative examples, the present invention effectively reduces the viscosity of the emulsion under the same conditions, thereby avoiding the problem of difficult dispersion caused by too high viscosity.
It should be understood that the above embodiments are merely for illustrating the technical concept and features of the present invention, and are intended to enable those skilled in the art to understand the present invention and implement the same according to the present invention without limiting the scope of the present invention. All equivalent changes or modifications made in accordance with the spirit of the present invention should be construed to be included in the scope of the present invention.
Claims (8)
1. The preparation method of the polyurethane associative thickener is characterized by comprising the following steps: the operation steps are as follows:
step one: adding 80-120 parts of polyethylene glycol into a reaction kettle filled with inert gas according to parts by mass, heating the reaction kettle to dehydrate for 2-4 hours, then adding a proper amount of catalyst and 2-10 parts of diisocyanate, and starting stirring to fully and uniformly mix;
Step two: heating the reaction kettle for 2-8h, adding 5-12 parts of synergistic agent into the kettle, continuously preserving heat for 4-10h, and vacuum drying the precipitate after the reaction is finished to obtain white solid, namely the polyurethane associative thickener;
the preparation method of the synergist in the second step comprises the following steps:
According to the mass parts, 12-24 parts of mercaptoglycerol, 6-10 parts of 1-methyl-5- (ethylene oxide-2-yl) -1H-pyrazole, 200-300 parts of ethanol and 2-5 parts of sodium ethoxide are slowly added into a reaction kettle, nitrogen is introduced, and the temperature is raised to 60-75 ℃ for reaction for 100-130min; adding 2-6 parts of N-vinyl caprolactam, and reacting at 60-75 ℃ for 60-100min; evaporating the ethanol to obtain the synergist.
2. The method for preparing a polyurethane associative thickener according to claim 1, wherein: the molecular weight of polyethylene glycol in the first step is 300-30000g/mol.
3. The method for preparing a polyurethane associative thickener according to claim 1, wherein: the dehydration temperature of the reaction kettle in the first step is 90-120 ℃, and the dehydration is carried out until the water content is not higher than 0.5%.
4. The method for preparing a polyurethane associative thickener according to claim 1, wherein: the dosage of the catalyst in the first step is 0.1-0.8wt% of the total mass of the polyethylene glycol and the diisocyanate.
5. The method for preparing a polyurethane associative thickener according to claim 1, wherein: the catalyst in the first step is at least one of stannous octoate, dibutyl tin dilaurate, dibutyl tin maleate and zinc octoate.
6. The method for preparing a polyurethane associative thickener according to claim 1, wherein: the diisocyanate in the first step is at least one selected from isophorone diisocyanate (IPDI), toluene Diisocyanate (TDI), methylcyclohexyl diisocyanate (HTDI), hexamethylene Diisocyanate (HDI), 4 '-diphenylmethane diisocyanate (MDI), 4' -dicyclohexylmethane diisocyanate (HMDI), 2, 6-diisocyanate methylhexanoate, xylylene Diisocyanate (XDI) and naphthalene-1, 5-diisocyanate (NDI).
7. The method for preparing a polyurethane associative thickener according to claim 1, wherein: the dehydration temperature of the reaction in the first step is 50-120 ℃.
8. The method for preparing a polyurethane associative thickener according to claim 1, wherein: and in the second step, the reaction temperature of the reaction kettle is 60-120 ℃.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101676332A (en) * | 2008-09-19 | 2010-03-24 | 罗门哈斯公司 | Thickener composition and method for thickening aqueous systems |
| CN113817131A (en) * | 2020-06-20 | 2021-12-21 | 万华化学集团股份有限公司 | Polyurethane thickener with dispersing function and preparation method and application thereof |
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| US5023309A (en) * | 1987-09-18 | 1991-06-11 | Rheox, Inc. | Water dispersible, modified polyurethane thickener with improved high shear viscosity in aqueous systems |
| KR101924770B1 (en) * | 2011-01-20 | 2018-12-04 | 바스프 에스이 | Dendritic polyether-polyurethane thickeners |
| CN114621397B (en) * | 2020-12-11 | 2024-04-09 | 万华化学集团股份有限公司 | Thickener for no-wash hand-washing liquid system and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101676332A (en) * | 2008-09-19 | 2010-03-24 | 罗门哈斯公司 | Thickener composition and method for thickening aqueous systems |
| CN113817131A (en) * | 2020-06-20 | 2021-12-21 | 万华化学集团股份有限公司 | Polyurethane thickener with dispersing function and preparation method and application thereof |
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