CN116162439A - Preparation method of polydopamine modified polysiloxane organic silica gel film - Google Patents

Preparation method of polydopamine modified polysiloxane organic silica gel film Download PDF

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CN116162439A
CN116162439A CN202211586664.1A CN202211586664A CN116162439A CN 116162439 A CN116162439 A CN 116162439A CN 202211586664 A CN202211586664 A CN 202211586664A CN 116162439 A CN116162439 A CN 116162439A
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modified polysiloxane
organosilicon
polydopamine
dopamine
adhesive film
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施克炜
胡明亮
陈雁军
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Taihu Jinzhang Technology Co ltd
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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
    • C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
    • C09J183/04—Polysiloxanes
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/0666—Polycondensates containing five-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms
    • C08G73/0672—Polycondensates containing five-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only one nitrogen atom in the ring
    • 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
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/08—Macromolecular additives
    • 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
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
    • 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
    • C09J2483/00—Presence of polysiloxane
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/10—Energy storage using batteries

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)

Abstract

The invention discloses a preparation method of a polydopamine modified polysiloxane organic silicon adhesive film, which specifically comprises the following steps: s1, preparing an organosilicon prepolymer; s2, mixing the organosilicon prepolymer with dopamine hydrochloride and then carrying out polymerization reaction; s3, adding an inhibitor and triethylamine to perform dopamine polymerization reaction; and S4, casting the product obtained in the step S3 into a film to obtain the organic silicon film of the polydopamine modified polysiloxane. According to the organic silica gel membrane, dopamine and the organic silicon prepolymer are polymerized in situ, and before the poly-dopamine is polymerized, the poly-dopamine is dispersed in the organic silicon prepolymer, and after the poly-dopamine is polymerized, the poly-dopamine can be more uniformly dispersed in the organic silica gel solution, so that acting force among organic silica gel molecules is enhanced, and the organic silica gel membrane has good impact resistance and heat resistance.

Description

Preparation method of polydopamine modified polysiloxane organic silica gel film
Technical Field
The invention relates to the technical field of preparation of organic silica gel films, in particular to a preparation method of a polydopamine modified polysiloxane organic silica gel film.
Background
The organosilicon polymer has the performances of reaction inertia, weather resistance and low surface energy, is widely applied, and has wide application prospect in the fields of cosmetics, textiles, medical materials, protective films and the like. In applications, silicone polymers are often required to meet more properties, such as mechanical properties, due to their requirements. In the traditional technology, filler is often added to modify the mechanical properties of the organosilicon polymer finished product, but because the particle size of the traditional filler is larger, the traditional filler is unevenly dispersed, such as nano silicon dioxide particles, the specific surface area of the traditional filler is higher, agglomeration is easy to occur, the traditional filler has important influence on the transparency and mechanical properties of an organosilicon adhesive film, and in addition, the raw materials with poor dispersibility can also cause the increase of processing difficulty.
Disclosure of Invention
Based on the technical problems in the background art, the invention provides a preparation method of a polydopamine modified polysiloxane organic silicon adhesive film, which has the advantages of small thermal expansion coefficient, strong impact resistance, high transparency and simple preparation process.
The invention provides a preparation method of a polydopamine modified polysiloxane organic silicon adhesive film, which specifically comprises the following steps:
s1, uniformly mixing vinyl-terminated organopolysiloxane, organic silicon resin and a cross-linking agent in a solvent to obtain an organic silicon prepolymer;
s2, mixing the organosilicon prepolymer in the step S1 with dopamine hydrochloride, and then adding a catalyst to perform polymerization reaction;
s3, adding an inhibitor into the reaction system in the step S2 to stop the reaction, and adding triethylamine to perform dopamine polymerization reaction;
and S4, removing the solvent from the product obtained in the step S3, performing vacuum defoaming, and then casting to form a film to obtain the organic silicon film of the polydopamine modified polysiloxane.
Preferably, in S1, the vinyl-terminated organopolysiloxane is methyl vinyl silicone rubber, and the vinyl-terminated polysiloxane has a vinyl content of 0.07mol% to 0.5mol%.
Preferably, in S1, the weight percentage of the vinyl-terminated organopolysiloxane, the silicone resin and the cross-linking agent in the total amount of the three is 60-80:20-40:1-2.
Preferably, in S1, the silicone resin is at least one or several of methylsilane, methylvinylsilane and methylphenylsilane.
Preferably, the cross-linking agent is at least one of methyl silicone oil, amino silicone oil, epoxy silicone oil and alcohol hydroxyl silicone oil.
Preferably, in S2, the weight ratio of the organosilicon prepolymer to the dopamine hydrochloride is 2-10:0.5-1.
Preferably, in the step S2, the catalyst is chloroplatinic acid, and the addition amount of the catalyst is 0.5% -1.0% of the weight of the organosilicon prepolymer.
Preferably, in S2, the reaction time is 0.5 to 5 hours and the reaction temperature is 60 to 70 ℃.
Preferably, in S3, the inhibitor is 3-methyl-1-butyn-3-ol, 1-alkynyl cyclohexanol, 3, 5-dimethyl-ethyn-3-ol, 3-methyl-1-penten-3-ol; the addition amount of the inhibitor is 0.05% -0.5% of the organosilicon prepolymer.
Preferably, in S3, the mass ratio of the triethylamine to the dopamine hydrochloride is 0.5-1.5:10; the polymerization time of the dopamine is 3-5h, and the reaction temperature is 50-70 ℃.
The beneficial effects are that: according to the invention, after the dopamine hydrochloride and the organosilicon prepolymer are fully mixed, active groups on dopamine molecules and the organosilicon prepolymer generate intermolecular acting force, so that the dopamine can be uniformly distributed among the prepolymer molecules, the dopamine can be oxidized and polymerized to form polydopamine in polymerized organosilicon glue solution, the polydopamine has higher viscosity, the intra-molecular cohesiveness of the organosilicon glue solution can be increased, and after a silica gel film is formed, the impact resistance after film formation can be obviously improved, and the molecules are difficult to disperse after being subjected to external force. Also, the polydopamine having viscosity can block the diffusion movement of the silica gel molecules when the ambient temperature increases, thereby reducing the thermal expansion coefficient.
Detailed Description
The technical scheme of the invention is described in detail through specific embodiments.
Example 1
The preparation method of the polydopamine modified polysiloxane organic silica gel film specifically comprises the following steps:
s1, uniformly mixing methyl vinyl silicone rubber 110-1, methyl vinyl silane and hydroxyl silicone oil in a solvent to obtain an organosilicon prepolymer; the weight ratio of the 110-1 silicon rubber to the methyl vinyl silane to the hydroxyl silicone oil is 70:29:1;
s2, mixing the organosilicon prepolymer in the step S1 with dopamine hydrochloride, adding chloroplatinic acid, and reacting for 4.5 hours at 65 ℃; the weight ratio of the organosilicon prepolymer to the dopamine hydrochloride is 10:1; the addition amount of the chloroplatinic acid is 0.5% of the weight of the 110-1 silicone rubber;
s3, adding 1-alkynyl cyclohexanol in the reaction system of S2, wherein the addition amount is 0.05% of the weight of the organosilicon prepolymer, stopping the reaction, adding triethylamine, and reacting for 4 hours at 60 ℃; the mass ratio of the triethylamine to the dopamine hydrochloride is 1:10;
and S4, removing the solvent from the product obtained in the step S3, performing vacuum defoaming, and then casting to form a film to obtain the organic silicon film of the polydopamine modified polysiloxane.
Example 2
The preparation method of the polydopamine modified polysiloxane organic silica gel film specifically comprises the following steps:
s1, uniformly mixing methyl vinyl silicone rubber 110-2, methyl vinyl silane and hydroxyl silicone oil in a solvent to obtain an organosilicon prepolymer; the weight ratio of the 110-2 silicon rubber to the methylsilane to the epoxy silicone oil is 75:23:2;
s2, mixing the organosilicon prepolymer in the step S1 with dopamine hydrochloride, adding chloroplatinic acid, and reacting for 4.5 hours at 65 ℃; the weight ratio of the organosilicon prepolymer to the dopamine hydrochloride is 10:2; the addition amount of the chloroplatinic acid is 0.7% of the weight of 110-2 silicone rubber;
s3, adding 3-methyl-1-pentene-3-ol into the reaction system in the S2, wherein the addition amount is 0.1% of the weight of the organosilicon prepolymer, stopping the reaction, adding triethylamine, and reacting for 4 hours at 60 ℃; the mass ratio of the triethylamine to the dopamine hydrochloride is 1:10;
and S4, removing the solvent from the product obtained in the step S3, performing vacuum defoaming, and then casting to form a film to obtain the organic silicon film of the polydopamine modified polysiloxane.
Example 3:
the preparation method of the polydopamine modified polysiloxane organic silica gel film specifically comprises the following steps:
s1, uniformly mixing methyl vinyl silicone rubber 110-3, methyl vinyl silane and hydroxyl silicone oil in a solvent to obtain an organosilicon prepolymer; the weight ratio of the 110-3 silicon rubber to the methylsilane to the epoxy silicone oil is 60:38:2;
s2, mixing the organosilicon prepolymer in the step S1 with dopamine hydrochloride, adding chloroplatinic acid, and reacting for 4.5 hours at 65 ℃; the weight ratio of the organosilicon prepolymer to the dopamine hydrochloride is 10:5; the addition amount of the chloroplatinic acid is 0.5% of the weight of 110-3 silicone rubber;
s3, adding 3-methyl-1-butine-3-alcohol into the reaction system in the S2, wherein the addition amount is 0.05% of the weight of the organosilicon prepolymer, stopping the reaction, adding triethylamine, and reacting for 4 hours at 60 ℃; the mass ratio of the triethylamine to the dopamine hydrochloride is 1:10;
and S4, removing the solvent from the product obtained in the step S3, performing vacuum defoaming, and then casting to form a film to obtain the organic silicon film of the polydopamine modified polysiloxane.
Example 4
The preparation method of the polydopamine modified polysiloxane organic silica gel film specifically comprises the following steps:
s1, uniformly mixing methyl vinyl silicone rubber 110-1, methyl vinyl silane and hydroxyl silicone oil in a solvent to obtain an organosilicon prepolymer; the weight ratio of the 110-1 silicon rubber to the methyl vinyl silane to the hydroxyl silicone oil is 65:34:1;
s2, mixing the organosilicon prepolymer in the step S1 with dopamine hydrochloride, adding chloroplatinic acid, and reacting for 4.5 hours at 65 ℃; the weight ratio of the organosilicon prepolymer to the dopamine hydrochloride is 10:0.5; the addition amount of the chloroplatinic acid is 1% of the weight of the 110-1 silicone rubber;
s3, adding 1-alkynyl cyclohexanol in the reaction system of S2, wherein the addition amount is 0.15% of the weight of the organosilicon prepolymer, stopping the reaction, adding triethylamine, and reacting for 4 hours at 60 ℃; the mass ratio of the triethylamine to the dopamine hydrochloride is 1:10;
and S4, removing the solvent from the product obtained in the step S3, performing vacuum defoaming, and then casting to form a film to obtain the organic silicon film of the polydopamine modified polysiloxane.
Comparative example 1
The preparation method of the organic silicon adhesive film specifically comprises the following steps:
s1, uniformly mixing methyl vinyl silicone rubber 110-1, methyl vinyl silane and hydroxyl silicone oil in a solvent to obtain an organosilicon prepolymer; the weight ratio of the 110-1 silicon rubber to the methyl vinyl silane to the hydroxyl silicone oil is 70:29:1;
s2, reacting the organosilicon prepolymer in the step S1 with chloroplatinic acid at 65 ℃ for 4.5 hours; the addition amount of the chloroplatinic acid is 0.5% of the weight of the 110-1 silicone rubber;
s3, adding 1-alkynyl cyclohexanol in the reaction system of S2, wherein the addition amount is 0.05% of the weight of the organosilicon prepolymer, and stopping the reaction;
and S4, removing the solvent from the product obtained in the step S3, performing vacuum defoaming, and then casting to form a film to obtain the organic silicon adhesive film.
Comparative example 2
The preparation method of the polydopamine modified polysiloxane organic silica gel film specifically comprises the following steps:
s1, uniformly mixing methyl vinyl silicone rubber 110-1, methyl vinyl silane and hydroxyl silicone oil in a solvent to obtain an organosilicon prepolymer; the weight ratio of the 110-1 silicon rubber to the methyl vinyl silane to the hydroxyl silicone oil is 70:29:1;
s2, mixing the organosilicon prepolymer in the step S1 with silicon dioxide nano particles, adding chloroplatinic acid, and reacting for 4.5 hours at 65 ℃; the weight ratio of the organosilicon prepolymer to the silicon dioxide is 10:1; the addition amount of the chloroplatinic acid is 0.5% of the weight of the 110-1 silicone rubber;
s3, adding 1-alkynyl cyclohexanol in the reaction system of S2, wherein the addition amount is 0.05% of the weight of the organosilicon prepolymer, and stopping the reaction;
and S4, removing the solvent from the product obtained in the step S3, performing vacuum defoaming, and then casting to form a film to obtain the organic silicon film of the polydopamine modified polysiloxane. .
The polyimide films prepared in examples 1 to 4 and comparative examples 1 to 2 were tested for properties:
optical performance test:
the light transmittance and haze of the above silicone adhesive film were measured according to ASTM D1003.
And (3) hardness detection:
the hardness (A) of the organosilicon adhesive film is detected by using GB 2411-1980 method for testing Shore hardness of plastics.
And (3) thermal expansion coefficient detection:
the coefficient of thermal expansion of the above-mentioned silicone films was measured using ISO 11359-2-1999 Plastic thermodynamic analysis (TMA) part 2, determination of coefficient of linear thermal expansion and glass transition temperature.
Elongation at break detection:
the elongation at break (%) of the above-mentioned silicone adhesive film was measured by using GB/T1701-2001 "determination of tensile Strength and elongation at break of hard rubber".
After the performance test, the test results are shown in the following table:
Figure BDA0003991885400000071
compared with the comparative example 1, the optical performance of the polymer dopamine tiny particles formed in the glue solution is slightly reduced due to the polymerization of the dopamine, compared with the filler commonly used in the field, such as the organic silica gel film prepared in the comparative example 2, the light transmittance is obviously improved, and meanwhile, the organic silica gel film prepared in the invention is lower in haze. Therefore, the organic silica gel film obtained by the preparation method can meet the requirement on optical performance.
From the mechanical property aspect, the organic silicon adhesive film of the polydopamine modified polysiloxane prepared by the invention can strengthen intermolecular acting force and cohesive force in the adhesive body, so that the organic silicon adhesive films prepared in examples 1-4 have higher hardness and elongation at break.
From the thermodynamic property, the organic silica gel membrane molecules prepared in the examples 1-4 contain a certain amount of polydopamine which has rich amino, imino and other active groups, have higher adhesiveness, and can avoid the molecules from performing dispersion movement under the condition of heating, so that the thermal expansion coefficient of the molecules is reduced, and the heat resistance of the molecules is improved.
The foregoing is only a preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art, who is within the scope of the present invention, should make equivalent substitutions or modifications according to the technical scheme of the present invention and the inventive concept thereof, and should be covered by the scope of the present invention.

Claims (10)

1. The preparation method of the polydopamine modified polysiloxane organic silica gel film is characterized by comprising the following steps of:
s1, uniformly mixing vinyl-terminated organopolysiloxane, organic silicon resin and a cross-linking agent in a solvent to obtain an organic silicon prepolymer;
s2, mixing the organosilicon prepolymer in the step S1 with dopamine hydrochloride, and then adding a catalyst to perform polymerization reaction;
s3, adding an inhibitor into the reaction system in the step S2 to stop the reaction, and adding triethylamine to perform dopamine polymerization reaction;
and S4, removing the solvent from the product obtained in the step S3, performing vacuum defoaming, and then casting to form a film to obtain the organic silicon film of the polydopamine modified polysiloxane.
2. The method for producing a polydopamine-modified polysiloxane silicone adhesive film according to claim 1, wherein in S1, the vinyl-terminated organopolysiloxane is methyl vinyl silicone rubber, and the vinyl content of the vinyl-terminated polysiloxane is 0.07mol% to 0.5mol%.
3. The method for preparing a polydopamine modified polysiloxane organosilicon adhesive film according to claim 1, wherein in S1, the weight percentage of the vinyl terminated organopolysiloxane, the organosilicon resin and the cross-linking agent in the total amount of the three is 60-80:10-30:1-2.
4. The method for preparing a polydopamine modified polysiloxane organosilicon adhesive film according to claim 1, wherein in S1, the organosilicon resin is at least one or more of methylsilane, methylvinylsilane and methylphenylsilane.
5. The method for producing a polydopamine-modified polysiloxane silicone adhesive film according to claim 1, wherein in S1, the crosslinking agent is at least one of methyl silicone oil, amino silicone oil, epoxy silicone oil, and alcoholic hydroxyl silicone oil.
6. The method for preparing a polydopamine modified polysiloxane organosilicon adhesive film according to claim 1, wherein in S2, the weight ratio of the organosilicon prepolymer to dopamine hydrochloride is 1:2-10.
7. The method for preparing a polydopamine modified polysiloxane organosilicon adhesive film according to claim 1, wherein in S2, the catalyst is chloroplatinic acid, and the catalyst is added in an amount of 0.5% -1.0% by weight of the organosilicon prepolymer.
8. The method for preparing a polydopamine modified polysiloxane silicone adhesive film according to claim 1, wherein in S2, the reaction time is 0.5-5h, and the reaction temperature is 60-70 ℃.
9. The method for producing a polydopamine-modified polysiloxane silicone adhesive film according to claim 1, characterized in that in S3, the inhibitor is 3-methyl-1-butyn-3-ol, 1-alkynyl cyclohexanol, 3, 5-dimethyl-ethyn-3-ol, 3-methyl-1-penten-3-ol; the addition amount of the inhibitor is 0.05% -0.5% of the organosilicon prepolymer.
10. The method for preparing a polydopamine modified polysiloxane organosilicon adhesive film according to claim 1, wherein in S3, the mass ratio of triethylamine to dopamine hydrochloride is 0.5-1.5:10; the polymerization time of the dopamine is 3-5h, and the reaction temperature is 50-70 ℃.
CN202211586664.1A 2022-12-09 2022-12-09 Preparation method of polydopamine modified polysiloxane organic silica gel film Pending CN116162439A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116948525A (en) * 2023-07-03 2023-10-27 广州大学 Organosilicon coating and preparation method and application thereof
CN117567747A (en) * 2024-01-16 2024-02-20 深圳先进电子材料国际创新研究院 Surfactant for underfill, and preparation method and application thereof
CN117820705A (en) * 2023-12-22 2024-04-05 深圳市锦联科技有限公司 Organic silicon heat conduction gasket and preparation method thereof

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116948525A (en) * 2023-07-03 2023-10-27 广州大学 Organosilicon coating and preparation method and application thereof
CN117820705A (en) * 2023-12-22 2024-04-05 深圳市锦联科技有限公司 Organic silicon heat conduction gasket and preparation method thereof
CN117567747A (en) * 2024-01-16 2024-02-20 深圳先进电子材料国际创新研究院 Surfactant for underfill, and preparation method and application thereof
CN117567747B (en) * 2024-01-16 2024-04-09 深圳先进电子材料国际创新研究院 Surfactant for underfill, and preparation method and application thereof

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