CN116333654A - Terpolymer adhesive tape type dry-wet dual-purpose adhesive and preparation method and application thereof - Google Patents

Terpolymer adhesive tape type dry-wet dual-purpose adhesive and preparation method and application thereof Download PDF

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Publication number
CN116333654A
CN116333654A CN202310350906.5A CN202310350906A CN116333654A CN 116333654 A CN116333654 A CN 116333654A CN 202310350906 A CN202310350906 A CN 202310350906A CN 116333654 A CN116333654 A CN 116333654A
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adhesive
terpolymer
tape type
type dry
wet dual
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朱世平
邱文莲
张祺
黄逸
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Chinese University of Hong Kong Shenzhen
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Chinese University of Hong Kong Shenzhen
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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
    • 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
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1807—C7-(meth)acrylate, e.g. heptyl (meth)acrylate or benzyl (meth)acrylate
    • 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
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • 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
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • C09J7/22—Plastics; Metallised plastics
    • C09J7/25—Plastics; Metallised plastics based on macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C09J7/255—Polyesters
    • 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
    • C09J2433/00—Presence of (meth)acrylic polymer
    • 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
    • C09J2467/00—Presence of polyester
    • C09J2467/006—Presence of polyester in the substrate
    • 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 Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesive Tapes (AREA)

Abstract

The application provides a terpolymer adhesive tape type dry-wet dual-purpose adhesive, and a preparation method and application thereof, and relates to the field of materials. The terpolymer adhesive tape type dry-wet dual-purpose adhesive is prepared from raw materials including benzyl acrylate, trimethyl acryloxyethyl ammonium bistrifluoromethane sulfonyl imide, poly (ethylene glycol) methyl ether acrylate and an initiator through free radical polymerization. The preparation method comprises the following steps: and mixing the raw materials to obtain a precursor solution, and then carrying out polymerization reaction to obtain the terpolymer adhesive tape type dry-wet dual-purpose adhesive. The terpolymer tape type dry-wet dual-purpose adhesive is used for bonding in air and underwater. The terpolymer tape type dry-wet dual-purpose adhesive provided by the application is simple in preparation raw materials, does not need to use a monomer material containing catechol functional groups, is simple in preparation process, and can realize instant strong adhesion to the surfaces of plastic substrates such as PET, PMMA, PTFE in air and underwater.

Description

Terpolymer adhesive tape type dry-wet dual-purpose adhesive and preparation method and application thereof
Technical Field
The application relates to the field of materials, in particular to a terpolymer adhesive tape type dry-wet dual-purpose adhesive, a preparation method and application thereof.
Background
Adhesives are widely used in our daily life and in industrial production, such as sticky notes and adhesive bandages. The combination of interfacial adhesion and bulk strength is critical to achieving high adhesion. Most commercial adhesives are liquid materials with excellent wetting and weaker cohesive strength before use; in use, the liquid adhesive is in sufficient contact with the substrate and cures to form a solid material with strong cohesion to bond the adherent objects together. Most commercial adhesives achieve an efficient and long-lasting bonding effect in a dry environment, such as 502 glue. However, achieving adhesion of adhesives to substrate surfaces in an underwater environment presents difficulties and challenges. This is because the hydration layer formed on the surface of the substrate blocks the effective contact with the adhesive, and the interaction between the two is difficult to form on a molecular level; in addition, water tends to become trapped in the adhesion interface, macroscopically reducing the contact area between the two, resulting in the interface being difficult to adhere. Indeed, in many applications, it is desirable that the adhesive be in contact with a non-dry surface or be immersed in an aqueous medium to adhere to a substrate, such as implantable medical devices, wound dressings, water-based energy devices, underwater sensors, underwater repair, and the marine industry. Therefore, developing adhesives that can be suitable for various underwater environments to meet different application scenarios has become a new research hotspot gradually.
Removal of the hydration layer is critical to achieving underwater adhesion and may be accomplished by absorbing or removing the aqueous layer. Materials for removing the water layer based on the absorption principle are mostly gel materials, including hydrogels and organogels. However, the gel-type adhesive has the problem of unstable material performance caused by easy evaporation or leakage of liquid. The adhesive for removing the water layer based on the hydrophobic principle is generally realized through hydrophobic components, most of materials are polymer materials without liquid or high-boiling point ionic liquid, the worry of unstable performance caused by the loss of liquid components can be avoided, and the adhesive has higher storage stability than gel adhesives. At present, catechol is used as a side chain to prepare the underwater adhesive, and the catechol has the characteristics of both a hydrophobic benzene ring and a hydrophilic hydroxyl group, so that the material has good adhesion effect, but the catechol has the problems of performance reduction and even failure caused by easy oxidation into a quinone structure, and the preparation cost is high.
The adhesives are classified into glue type and tape type according to different bonding modes. Glue-type adhesives are generally composed of polymerizable or crosslinkable monomers or oligomers, with molecular level interfacial interactions occurring during underwater curing. Subsequently, the liquid forms a solid by polymerization/cross-linking. The glue type adhesive has high wettability to the surface of a substrate, generally has better interface bonding strength, but requires additional curing time when in use, can not be reused after curing, and is easy to leave residual glue when in debonding. In contrast, the adhesive tape type adhesive is made of a polymer with lower modulus, mainly realizes underwater adhesion through intermolecular interaction, and has the characteristics of instant adhesion and reusability. However, the adhesive tape type adhesive has lower wettability to the surface of the substrate than the adhesive tape type adhesive, and is easy to cause interface bonding failure. Therefore, development of the glue type adhesive focuses on design of chemical structure thereof to ensure stronger cohesive force; the design of the adhesive tape type adhesive is more focused on breaking the hydration layer on the surface of the substrate and realizing stronger interaction with the substrate.
Disclosure of Invention
The application aims to provide a terpolymer adhesive tape type dry-wet dual-purpose adhesive, and a preparation method and application thereof, so as to solve the problems.
In order to achieve the above purpose, the present application adopts the following technical scheme:
a terpolymer adhesive tape type dry-wet adhesive is prepared from benzyl acrylate, trimethyl acryloxyethyl ammonium bistrifluoromethane sulfonyl imide, poly (ethylene glycol) methyl ether acrylate and initiator through free radical polymerization.
The application also provides a preparation method of the terpolymer tape type dry-wet dual-purpose adhesive, which comprises the following steps:
and mixing the raw materials to obtain a precursor solution, and then carrying out polymerization reaction to obtain the terpolymer tape type underwater adhesive.
Preferably, the molecular weight of the poly (ethylene glycol) methyl ether acrylate is 1000 or less.
Preferably, the initiator comprises a photoinitiator or a thermal initiator;
the photoinitiator comprises one or more of 2, 2-diethoxyacetophenone, benzophenone, irgacure 184 and Irgacure 819, and the thermal initiator comprises 2, 2-azobisisobutyronitrile and/or benzoyl peroxide.
Preferably, the molar ratio of the benzyl acrylate to the trimethylacryloyloxyethyl ammonium bistrifluoromethane sulfonimide is (1-4): 1.
preferably, the ratio of the poly (ethylene glycol) methyl ether acrylate to the total molar amount of benzyl acrylate and the trimethylacryloyloxyethyl ammonium bis-trifluoromethanesulfonyl imide is (0.1-0.3): 1.
preferably, the ratio of the amount of the initiator to the total molar amount of the benzyl acrylate, the trimethylammonium acryloyloxyethyl bis-trifluoromethanesulfonyl imide, and the poly (ethylene glycol) methyl ether acrylate is 0.005 to 0.02:1.
preferably, the polymerization is carried out at normal temperature for a period of 0.5 to 4 hours, or at 60 to 70 ℃ for a period of 8 to 12 hours.
Preferably, the polymerization reaction is carried out in a mold;
the die comprises an upper base material, a PET release film, a gasket, a PET common film and a lower base material which are sequentially stacked, wherein the PET release film, the gasket and the PET common film form a containing space for containing the precursor liquid.
The application also provides application of the terpolymer tape type dry-wet dual-purpose adhesive, which is used for bonding in air and underwater.
Compared with the prior art, the beneficial effects of this application include:
the terpolymer adhesive tape type dry-wet dual-purpose adhesive provided by the application uses benzyl acrylate, trimethyl acryloyloxyethyl ammonium bistrifluoromethane sulfonyl imide and poly (ethylene glycol) methyl ether acrylate as monomers, does not need to be used for synthesizing complex catechol functional group-containing monomer materials, and can realize instant strong adhesion to the surfaces of plastic substrates such as PET, PMMA, PTFE in air and underwater. The terpolymer adhesive tape type dry-wet dual-purpose adhesive can form hydrogen bonds, pi-pi interactions, cation-pi interactions, hydrophobic interactions and the like with an adhesion substrate, and can keep good wetting of a plastic substrate under water and form a strong adhesion effect. Taking PET substrate as an example, 90-degree peeling test shows that the prepared underwater adhesive can adhere to the substrate by about 1100N/m after adhesion in air or water. In addition, the adhesive also has good adaptability to acid-base environment and high-salinity environment. The adhesive can be applied to pH=3, pH=11 and artificial seawater environments, and can still generate strong adhesion of 955, 968 and 948N/m with PET substrates. Meanwhile, the terpolymer adhesive tape type dry-wet dual-purpose adhesive also has good mechanical properties, and a tensile test shows that the copolymer can be stretched to be close to 14 times and reach the strength of 0.38MPa, so that the adhesive has high adhesion and better cohesive force, and can realize the effect of repeatable adhesion. It was found from the test that, for PET substrates, after 10 cycles of adhesion and peeling, adhesion to substrates of approximately 1100N/mm was still achieved. The dry-wet dual-purpose adhesive has long-term storage stability and unchanged adhesive force after being placed for several months under the environmental condition.
The preparation method of the terpolymer adhesive tape type dry-wet dual-purpose adhesive is simple in preparation process.
The terpolymer tape type dry-wet dual-purpose adhesive can be widely used for bonding in air and underwater.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present application, the drawings that are needed in the embodiments will be briefly described below, it being understood that the following drawings only illustrate certain embodiments of the present application and therefore should not be considered as limiting the scope of the present application.
FIG. 1 is a schematic view of a mold used in the examples;
fig. 2 is a 90 ° peel photograph of an example adhered PET substrate.
Detailed Description
The term as used herein:
"prepared from … …" is synonymous with "comprising". The terms "comprising," "including," "having," "containing," or any other variation thereof, as used herein, are intended to cover a non-exclusive inclusion. For example, a composition, step, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, step, method, article, or apparatus.
The conjunction "consisting of … …" excludes any unspecified element, step or component. If used in a claim, such phrase will cause the claim to be closed, such that it does not include materials other than those described, except for conventional impurities associated therewith. When the phrase "consisting of … …" appears in a clause of the claim body, rather than immediately following the subject, it is limited to only the elements described in that clause; other elements are not excluded from the stated claims as a whole.
When an equivalent, concentration, or other value or parameter is expressed as a range, preferred range, or a range bounded by a list of upper preferable values and lower preferable values, this is to be understood as specifically disclosing all ranges formed from any pair of any upper range limit or preferred value and any lower range limit or preferred value, regardless of whether ranges are separately disclosed. For example, when ranges of "1 to 5" are disclosed, the described ranges should be construed to include ranges of "1 to 4", "1 to 3", "1 to 2 and 4 to 5", "1 to 3 and 5", and the like. When a numerical range is described herein, unless otherwise indicated, the range is intended to include its endpoints and all integers and fractions within the range.
In these examples, the parts and percentages are by mass unless otherwise indicated.
"parts by mass" means a basic unit of measurement showing the mass ratio of a plurality of components, and 1 part may be any unit mass, for example, 1g may be expressed, 2.689g may be expressed, and the like. If we say that the mass part of the a component is a part and the mass part of the B component is B part, the ratio a of the mass of the a component to the mass of the B component is represented as: b. alternatively, the mass of the A component is aK, and the mass of the B component is bK (K is an arbitrary number and represents a multiple factor). It is not misunderstood that the sum of the parts by mass of all the components is not limited to 100 parts, unlike the parts by mass.
"and/or" is used to indicate that one or both of the illustrated cases may occur, e.g., a and/or B include (a and B) and (a or B).
A terpolymer adhesive tape type dry-wet adhesive is prepared from benzyl acrylate, trimethyl acryloxyethyl ammonium bistrifluoromethane sulfonyl imide, poly (ethylene glycol) methyl ether acrylate and initiator through free radical polymerization.
The structural formulas of the three monomers are shown as follows:
Figure BDA0004161553880000061
the structural formulas of benzyl acrylate (BzA), trimethylammoniumethoxyethylammonium bistrifluoromethane sulfonyl imide (AETATATISI) and poly (ethylene glycol) methyl ether acrylate (OEGA) respectively correspond to (a), (b) and (c) in sequence, and the monomers are arranged randomly after copolymerization.
The application also provides a preparation method of the terpolymer tape type dry-wet dual-purpose adhesive, which comprises the following steps:
and mixing the raw materials to obtain a precursor solution, and then carrying out polymerization reaction to obtain the ternary random copolymer adhesive tape type underwater adhesive.
In an alternative embodiment, the poly (ethylene glycol) methyl ether acrylate has a molecular weight of 1000 or less to avoid polymer crystallization.
In an alternative embodiment, the initiator comprises a photoinitiator or a thermal initiator;
the photoinitiator comprises one or more of 2, 2-diethoxyacetophenone, benzophenone, irgacure 184 and Irgacure 819, and the thermal initiator comprises 2, 2-azobisisobutyronitrile and/or benzoyl peroxide.
In an alternative embodiment, the molar ratio of benzyl acrylate to the trimethylacryloyloxyethyl ammonium bis trifluoromethanesulfonyl imide is (1-4): 1.
alternatively, the molar ratio of the benzyl acrylate to the trimethylacryloyloxyethyl ammonium bis-trifluoromethanesulfonyl imide may be 1: 1. 2:1. 3: 1. 4:1 or (1-4): any value between 1.
In an alternative embodiment, the ratio of the poly (ethylene glycol) methyl ether acrylate to the total molar amount of benzyl acrylate and the trimethylacryloyloxyethyl ammonium bistrifluoromethane sulfonimide is (0.1-0.3): 1.
alternatively, the ratio of the poly (ethylene glycol) methyl ether acrylate to the total molar amount of benzyl acrylate and the trimethylacryloyloxyethyl ammonium bis-trifluoromethanesulfonyl imide may be 0.1: 1. 0.2: 1. 0.3:1 or (0.1-0.3): any value between 1.
In an alternative embodiment, the initiator is used in a ratio of 0.005 to 0.02 to the total molar amount of benzyl acrylate, the trimethylacryloyloxyethyl ammonium bistrifluoromethane sulfonimide, and the poly (ethylene glycol) methyl ether acrylate: 1.
alternatively, the ratio of the amount of the initiator to the total molar amount of the benzyl acrylate, the trimethylacryloxyethyl ammonium bistrifluoromethane sulfonimide, the poly (ethylene glycol) methyl ether acrylate may be 0.005: 1. 0.01: 1. 0.015: 1. 0.02:1 or 0.005-0.02: any value between 1.
In an alternative embodiment, the polymerization is carried out at ambient temperature for a period of time ranging from 0.5 to 4 hours or from 60 to 70 ℃ for a period of time ranging from 8 to 12 hours.
Alternatively, the polymerization reaction is carried out at normal temperature for any value of 0.5h, 1h, 1.5h, 2h, 2.5h, 3h, 3.5h, 4h or 0.5-4 h; or 60 ℃, 61 ℃, 62 ℃, 63 ℃, 64 ℃, 65 ℃, 66 ℃, 67 ℃, 68 ℃, 69 ℃, 70 ℃ or any value between 60 and 70 ℃ for any value of 8 hours, 9 hours, 10 hours, 11 hours, 12 hours or any value between 8 and 12 hours.
In an alternative embodiment, the polymerization is carried out in a mold;
the die comprises an upper base material, a PET release film, a gasket, a PET common film and a lower base material which are sequentially stacked, wherein the PET release film, the gasket and the PET common film form a containing space for containing the precursor liquid.
The application also provides application of the terpolymer tape type dry-wet dual-purpose adhesive, which is mainly used for underwater bonding and can also be used for bonding in air.
Embodiments of the present application will be described in detail below with reference to specific examples, but it will be understood by those skilled in the art that the following examples are only for illustration of the present application and should not be construed as limiting the scope of the present application. The specific conditions are not noted in the examples and are carried out according to conventional conditions or conditions recommended by the manufacturer. The reagents or apparatus used were conventional products commercially available without the manufacturer's attention.
First, a mold used in the embodiment of the present application will be described.
As shown in FIG. 1, the mold comprises an upper substrate, a PET release film, a gasket, a PET common film and a lower substrate which are sequentially laminated, wherein the upper substrate and the lower substrate are both made of glass, the gasket is made of silica gel, is square, and has a thickness of 0.2-1.5mm; the PET release film, the gasket and the PET common film form a containing space for containing the precursor liquid.
Example 1
The embodiment provides a terpolymer tape type dry-wet dual-purpose adhesive, which is prepared by the following steps:
(1) Mixing monomer I benzyl acrylate (BzA), monomer II trimethyl acryloyloxyethyl ammonium bistrifluoromethane sulfonimide (AETATISI) and monomer III poly (ethylene glycol) methyl ether acrylate (OEGA), adding reagent IV2, 2-diethoxyacetophenone, and fully and uniformly mixing;
the molar ratio of the monomer I to the monomer II is 4:1; the amount of the monomer III is 0.1 mole ratio of the total amount of the monomer I and the monomer II; the molar ratio of reagent IV was 0.01 of the total of monomer I, monomer II and monomer III.
(2) Placing the PET release film and the common PET film on two sides of a gasket, placing a glass sheet, and clamping to obtain a die;
(3) Injecting the precursor liquid obtained in the step (1) into the die in the step (2), and carrying out polymerization reaction for 2h under the irradiation of 8W ultraviolet light;
(4) And after the reaction is finished, the material and the PET film are connected together and taken out, so that the terpolymer tape type underwater adhesive is obtained.
A 90 ° peel photograph of the resulting terpolymer tape type underwater adhesive adhered PET substrate is shown in fig. 2.
Example 2
The embodiment provides a terpolymer tape type dry-wet dual-purpose adhesive, which is prepared by the following steps:
(1) Mixing monomer I benzyl acrylate (BzA), monomer II trimethyl acryloyloxyethyl ammonium bistrifluoromethane sulfonimide (AETATISI) and monomer III poly (ethylene glycol) methyl ether acrylate (OEGA), adding reagent IV2, 2-diethoxyacetophenone, and fully and uniformly mixing;
the molar ratio of the monomer I to the monomer II is 2:1; the amount of the monomer III is 0.1 mole ratio of the total amount of the monomer I and the monomer II; the molar ratio of reagent IV was 0.01 of the total of monomer I, monomer II and monomer III.
(2) Placing the PET release film and the common PET film on two sides of a gasket, placing a glass sheet, and clamping to obtain a die;
(3) Injecting the precursor liquid obtained in the step (1) into the die in the step (2), and carrying out polymerization reaction for 1h under 36W ultraviolet irradiation;
(4) And after the reaction is finished, the material and the PET film are connected together and taken out, so that the terpolymer tape type underwater adhesive is obtained.
Example 3
The embodiment provides a terpolymer tape type dry-wet dual-purpose adhesive, which is prepared by the following steps:
(1) Mixing monomer I benzyl acrylate (BzA), monomer II trimethyl acryloyloxyethyl ammonium bistrifluoromethane sulfonimide (AETATISI) and monomer III poly (ethylene glycol) methyl ether acrylate (OEGA), adding reagent IV2, 2-diethoxyacetophenone, and fully and uniformly mixing;
the molar ratio of the monomer I to the monomer II is 1:1; the amount of the monomer III is 0.15 mole ratio of the total amount of the monomer I and the monomer II; the molar ratio of reagent IV was 0.01 of the total of monomer I, monomer II and monomer III.
(2) Placing the PET release film and the common PET film on two sides of a gasket, placing a glass sheet, and clamping to obtain a die;
(3) Injecting the precursor liquid obtained in the step (1) into the die in the step (2), and carrying out polymerization reaction for 0.5h under the irradiation of 100W ultraviolet light;
(4) And after the reaction is finished, the material and the PET film are connected together and taken out, so that the terpolymer tape type underwater adhesive is obtained.
Comparative example 1
Binary copolymer 1
(1) Mixing monomer I benzyl acrylate (BzA) with monomer II trimethyl acryloyloxyethyl ammonium bistrifluoromethane sulfonimide (AETATISS I), adding reagent IV2, 2-diethoxyacetophenone, and fully and uniformly mixing;
the molar ratio of the monomer I to the monomer II is 3:2; the molar ratio of reagent IV was 0.03 of the total amount of monomer I and monomer II.
(2) Placing the PET release film and the common PET film on two sides of a gasket, placing a glass sheet, and clamping to obtain a die;
(3) Injecting the precursor liquid obtained in the step (1) into the die in the step (2), and carrying out polymerization reaction for 4 hours under 8W ultraviolet irradiation;
(4) And after the reaction is finished, the material and the PET film are connected together and taken out, so that the binary copolymer adhesive tape type adhesive is obtained.
The Young modulus of the obtained binary copolymer tape adhesive is about 600MPa, the wettability to an adhesion surface is poor, and adhesion is carried out in air or under water, so that adhesion force is not generated to a PET substrate.
Comparative example 2
Binary copolymer 2
(1) Mixing monomer I benzyl acrylate (BzA) and monomer III poly (ethylene glycol) methyl ether acrylate (OEGA), adding reagent IV2, 2-diethoxyacetophenone, and fully and uniformly mixing;
the amount of the monomer III is 0.15 mole ratio of the monomer I; the molar ratio of reagent IV was 0.01 for monomer I.
(2) Placing the PET release film and the common PET film on two sides of a gasket, placing a glass sheet, and clamping to obtain a die;
(3) Injecting the precursor liquid obtained in the step (1) into the die in the step (2), and carrying out polymerization reaction for 2h under 8W ultraviolet irradiation;
(4) And after the reaction is finished, the material and the PET film are connected together and taken out, so that the binary copolymer adhesive tape type adhesive is obtained.
The obtained binary copolymer adhesive tape type adhesive does not contain cation-pi interaction, and the adhesion force generated by adhesion in air or under water to a PET substrate is 454N/m, which is lower than that of the proposed ternary copolymer adhesive tape type adhesive.
It should be noted that: adhesion was characterized using a 90 ° peel test calculated as force divided by tape width.
Finally, it should be noted that: the above embodiments are only for illustrating the technical solution of the present application, and not for limiting the same; although the present application has been described in detail with reference to the foregoing embodiments, it should be understood by those of ordinary skill in the art that: the technical scheme described in the foregoing embodiments can be modified or some or all of the technical features thereof can be replaced by equivalents; such modifications and substitutions do not depart from the spirit of the corresponding technical solutions from the scope of the technical solutions of the embodiments of the present application.
Furthermore, those skilled in the art will appreciate that while some embodiments herein include some features but not others included in other embodiments, combinations of features of different embodiments are meant to be within the scope of the present application and form different embodiments. For example, in the claims below, any of the claimed embodiments may be used in any combination. The information disclosed in this background section is only for enhancement of understanding of the general background of the application and should not be taken as an acknowledgement or any form of suggestion that this information forms the prior art already known to a person skilled in the art.

Claims (10)

1. A terpolymer adhesive tape type dry-wet dual-purpose adhesive is characterized by being prepared from raw materials including benzyl acrylate, trimethyl acryloxyethyl ammonium bistrifluoromethane sulfonyl imide, poly (ethylene glycol) methyl ether acrylate and an initiator through free radical polymerization.
2. A method for preparing the terpolymer tape type dry-wet dual-purpose adhesive according to claim 1, which is characterized by comprising the following steps:
and mixing the raw materials to obtain a precursor solution, and then carrying out polymerization reaction to obtain the terpolymer adhesive tape type dry-wet dual-purpose adhesive.
3. The method according to claim 2, wherein the molecular weight of the poly (ethylene glycol) methyl ether acrylate is 1000 or less.
4. The method of preparation according to claim 2, wherein the initiator comprises a photoinitiator or a thermal initiator;
the photoinitiator comprises one or more of 2, 2-diethoxyacetophenone, benzophenone, irgacure 184 and Irgacure 819, and the thermal initiator comprises 2, 2-azobisisobutyronitrile and/or benzoyl peroxide.
5. The method according to claim 2, wherein the molar ratio of the benzyl acrylate to the trimethylammonium acryloyloxyethyl bis (trifluoromethanesulfonyl) imide is (1-4): 1.
6. the method according to claim 2, wherein the ratio of the poly (ethylene glycol) methyl ether acrylate to the total molar amount of the benzyl acrylate and the trimethylammonium acryloyloxyethyl bistrifluoromethane sulfonyl imide is (0.1 to 0.3): 1.
7. the method according to claim 2, wherein the ratio of the amount of the initiator to the total molar amount of the benzyl acrylate, the trimethylammonioethyl acrylamide bistrifluoromethane sulfonimide, and the poly (ethylene glycol) methyl ether acrylate is 0.005 to 0.02:1.
8. the preparation method according to claim 2, wherein the polymerization is carried out at normal temperature for 0.5 to 4 hours or at 60 to 70 ℃ for 8 to 12 hours.
9. The method of any one of claims 2 to 8, wherein the polymerization reaction is performed in a mold;
the die comprises an upper base material, a PET release film, a gasket, a PET common film and a lower base material which are sequentially stacked, wherein the PET release film, the gasket and the PET common film form a containing space for containing the precursor liquid.
10. Use of the terpolymer tape type dry-wet dual-purpose adhesive according to claim 1, which is characterized by being used for air and underwater bonding.
CN202310350906.5A 2023-03-29 2023-03-29 Terpolymer adhesive tape type dry-wet dual-purpose adhesive and preparation method and application thereof Pending CN116333654A (en)

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