CN117106394A - Ultraviolet light curing adhesive for bonding membrane electrode of hydrogen fuel cell - Google Patents

Ultraviolet light curing adhesive for bonding membrane electrode of hydrogen fuel cell Download PDF

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Publication number
CN117106394A
CN117106394A CN202310197769.6A CN202310197769A CN117106394A CN 117106394 A CN117106394 A CN 117106394A CN 202310197769 A CN202310197769 A CN 202310197769A CN 117106394 A CN117106394 A CN 117106394A
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parts
acrylate
adhesive
trimethylbenzoyl
hydroxy
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CN117106394B (en
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刘秀棉
蒋文玲
丁龙奇
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Chongqing Zhongrun New Materials Co ltd
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Chongqing Zhongrun New Materials Co ltd
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    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/86—Inert electrodes with catalytic activity, e.g. for fuel cells
    • H01M4/8663—Selection of inactive substances as ingredients for catalytic active masses, e.g. binders, fillers
    • H01M4/8668—Binders
    • 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
    • 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
    • C09J11/02—Non-macromolecular additives
    • C09J11/04—Non-macromolecular additives inorganic
    • 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
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • 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
    • C09J153/00—Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
    • C09J153/02—Vinyl aromatic monomers and conjugated dienes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2203/00—Applications
    • C08L2203/20—Applications use in electrical or conductive gadgets
    • C08L2203/206—Applications use in electrical or conductive gadgets use in coating or encapsulating of electronic parts
    • 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
    • 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
    • C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
    • 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
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Fuel Cell (AREA)

Abstract

The application belongs to the technical field of membrane electrodes of hydrogen fuel cells, and particularly relates to an ultraviolet light curing adhesive for bonding membrane electrodes of hydrogen fuel cells, which comprises the following components: acrylic monomer, thermoplastic elastomer, tackifying resin, photoinitiator, thixotropic agent and silane coupling agent. The application provides an ultraviolet light curing adhesive which has better adhesive force, lower water absorption and better weather resistance for perfluorinated sulfonic acid resin films and PP and PE materials, and the adhesive can keep good peeling force and air tightness for a long time under high-temperature and high-humidity environments and realize batch automatic production.

Description

Ultraviolet light curing adhesive for bonding membrane electrode of hydrogen fuel cell
Technical Field
The application belongs to the technical field of membrane electrodes of hydrogen fuel cells, and relates to an ultraviolet light curing adhesive for bonding membrane electrodes of hydrogen fuel cells.
Background
The Membrane Electrode (MEA) is the most core component of the hydrogen fuel cell and consists of a cathode/anode catalytic layer, a proton exchange membrane and a cathode/anode diffusion layer 5. The diffusion layer plays roles of water management, material distribution, electron transfer and the like; the catalytic layer is a main place of electrochemical reaction, and relates to the generation of reaction, the transmission and emission of products and the like; the proton exchange membrane plays a role in transferring protons and preventing the short circuit of the cathode and the anode. Membrane Electrodes (MEA) are the core sites for a number of mass transport and electrochemical reactions, and their fabrication technology not only directly affects cell performance, but is also critical to reducing cell cost and increasing cell specific power and specific energy, and is symbolically known as the "heart" of a fuel cell.
The membrane electrode structure of the current proton exchange membrane fuel cell can be divided into two types according to the carrying mode of the catalytic layer, wherein one type is a GDE membrane electrode; the other is CCM membrane electrode. CCM (Catalyst-coated membrane) means a Catalyst coated membrane, and in the preparation process, the Catalyst is coated on two sides of a proton exchange membrane to form the CCM, and then a gas diffusion layer is hot-pressed on two sides of the CCM to form a membrane electrode. Compared with the GDE membrane electrode, the catalyst in the CCM membrane electrode is firmly combined with the proton membrane, is not easy to fall off, can effectively improve the interface resistance between the catalytic layer and the proton membrane, reduces the transmission resistance of protons on the interface, and has more excellent performance.
The preparation technology of CCM (Catalyst Coated Membrane ) membrane electrode is widely adopted at present, and is the main commercial preparation method at present. In the Membrane Electrode (MEA) manufacturing process, CCM needs to be bonded to a support material to achieve sealing and fixing effects. The Membrane Electrode (MEA) needs to be in a weakly acidic working environment with high temperature and high humidity for a long time and keeps good air tightness, so that an adhesive with low water absorption, high temperature and high humidity resistance, acid resistance and oxidation resistance is needed. Because the CCM consists of a catalyst layer and a proton exchange membrane, the membrane is generally a perfluorosulfonic acid resin membrane, and the support material is generally PET, PI, PEN, PP, PE and hydrocarbon polymers such as PC. The perfluorosulfonic acid resin film and the supporting material (except PC) have very low surface energy and are difficult to adhere, especially PP and PE, the traditional system has poor UV adhesive strength, high water absorption and poor boiling resistance, and can not keep good peeling force and air tightness in a long-term high-temperature and high-humidity environment.
The bonding performance of the CCM and the supporting material directly influences the production efficiency and the service life of the membrane electrode. Accordingly, it would be desirable to provide an adhesive suitable for use in a hydrogen fuel cell membrane electrode for bonding a CCM to a support material.
Disclosure of Invention
The application aims to provide an ultraviolet light curing adhesive for bonding membrane electrodes of hydrogen fuel cells.
In one aspect, the application provides an ultraviolet light curing adhesive, which is characterized by comprising the following components: acrylic monomer, thermoplastic elastomer, tackifying resin, photoinitiator, thixotropic agent and silane coupling agent;
wherein the adhesive uses the thermoplastic elastomer as a main resin.
In some embodiments, the adhesive comprises the following components in parts by weight: 20-85 parts of acrylic acid monomer, 10-55 parts of thermoplastic elastomer, 5-25 parts of tackifying resin, 1-15 parts of photoinitiator, 1-10 parts of thixotropic agent and 0.1-8 parts of silane coupling agent; preferably, the composition comprises the following components in parts by weight: 30-80 parts of acrylic acid monomer, 10-50 parts of thermoplastic elastomer, 5-20 parts of tackifying resin, 1-10 parts of photoinitiator, 1-9 parts of thixotropic agent and 0.5-7 parts of silane coupling agent; preferably, the composition comprises the following components in parts by weight: 50-80 parts of acrylic acid monomer, 15-45 parts of thermoplastic elastomer, 5-15 parts of tackifying resin, 1-8 parts of photoinitiator, 1-5 parts of thixotropic agent and 0.5-5 parts of silane coupling agent; preferably, the composition comprises the following components in parts by weight: 60-75 parts of acrylic acid monomer, 15-30 parts of thermoplastic elastomer, 5-10 parts of tackifying resin, 1-6 parts of photoinitiator, 1-4 parts of thixotropic agent and 1-4 parts of silane coupling agent; preferably, the composition comprises the following components in parts by weight: 65-70 parts of acrylic acid monomer, 20-25 parts of thermoplastic elastomer, 7-9 parts of tackifying resin, 3-5 parts of photoinitiator, 1-3 parts of thixotropic agent and 1-3 parts of silane coupling agent.
In some embodiments, the acrylate monomer is selected from one or more of a monofunctional acrylate, a difunctional acrylate, a multifunctional acrylate.
In some embodiments, the monofunctional acrylate is selected from one or more of methyl acrylate, ethyl acrylate, isobornyl acrylate, tetrahydrofuranyl acrylate, cyclotrimethylolpropane methylacrylate, 2-phenoxyethyl acrylate, 4-t-butylcyclohexyl acrylate, benzyl acrylate, 3, 5-trimethylcyclohexane acrylate.
In some embodiments, the difunctional acrylate is selected from one or more of 1, 6-hexanediol diacrylate, dipropylene glycol diacrylate, pentanediol diacrylate, tricyclodecane dimethanol diacrylate.
In some embodiments, the multifunctional acrylate is selected from one or more of trimethylolpropane triacrylate, ethoxylated trimethylolpropane triacrylate, propoxylated trimethylolpropane triacrylate, pentaerythritol triallyl ether, tris (2-hydroxyethyl) isocyanuric acid triacrylate, and dipentaerythritol pentaacrylate.
In some embodiments, the acrylate monomer is selected from the group consisting of isobornyl acrylate in combination with 2-phenoxyethyl acrylate.
In some embodiments, the weight ratio of isobornyl acrylate to 2-phenoxyethyl acrylate is from 5 to 15:45-65; preferably, the weight ratio of the isobornyl acrylate to the 2-phenoxyethyl acrylate is 8-12:50-60; preferably, the weight ratio of the isobornyl acrylate to the 2-phenoxyethyl acrylate is 10:57-60.
In some embodiments, the thermoplastic elastomer is selected from one or more of SBS, SIS, SEBS, SEPS.
In some embodiments, the thermoplastic elastomer is selected from SBS and/or SIS.
In some embodiments, the combined weight ratio of SBS to SIS in the thermoplastic elastomer is 5-15:10-20; preferably, the combined weight ratio of SBS to SIS in the thermoplastic elastomer is 8-12:12-18; preferably, the combined weight ratio of SBS to SIS in the thermoplastic elastomer is 10:15.
In some embodiments, the tackifying resin is selected from one or more of terpene resins, petroleum resins, hydrogenated petroleum resins, chlorinated polyolefins, rosin resins, hydrogenated rosin resins.
In some embodiments, the tackifying resin is selected from chlorinated polyolefin or rosin resins.
In some embodiments, the photoinitiator is selected from one or more of 2-hydroxy-2-methyl-1-phenyl ketone, 1-hydroxy-cyclohexyl-phenyl ketone, benzophenone, benzoin methyl ether, benzoin ethyl ether, benzoin butyl ether, a-dimethoxy-a-phenylacetophenone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, ethyl 2,4, 6-trimethylbenzoyl phenyl phosphonate, 2-methyl-1- [ 4-methylthiophenyl ] -2-morpholino-1-propanone, 2-isopropylthiazone ketone (2, 4 isomer mixture), 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone, and the like; preferably, the photoinitiator is selected from the group consisting of 1-hydroxy-cyclohexyl-phenyl-methanone and (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide; preferably, the combined weight ratio of the 1-hydroxy-cyclohexyl-phenyl ketone and the (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide is: 2-8:1-5; preferably, the combined weight ratio of the 1-hydroxy-cyclohexyl-phenyl ketone and the (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide is: 3-5:1-4.
In some embodiments, the thixotropic agent is selected from one or more of fumed silica, polyamide wax, hydrogenated castor oil; preferably, the thixotropic agent is selected from fumed silica.
In some embodiments, the silane coupling agent is selected from one or more of vinyl trimethoxysilane, vinyl triethoxysilane, gamma-aminopropyl triethoxysilane, gamma-glycidoxypropyl trimethoxysilane, gamma-methacryloxypropyl trimethoxysilane, N- (beta-aminoethyl) -gamma-aminopropyl trimethyloxy silane; preferably, the silane coupling agent is selected from gamma-methacryloxypropyl trimethoxysilane.
On the other hand, the application also provides a preparation method of the adhesive, which comprises the following steps:
(1) Adding acrylic acid monomer, thermoplastic elastomer and tackifying resin into a kettle of a power mixer which is heated and can be vacuumized, and heating to dissolve solids;
(2) After the solid is dissolved, stopping heating, adding the photoinitiator, the thixotropic agent and the silane coupling agent, keeping out of the sun, continuously stirring to completely dissolve the photoinitiator, uniformly dispersing the thixotropic agent, and finally carrying out vacuum defoaming to obtain the ultraviolet light curing adhesive.
In some embodiments, in step (1), the heating temperature at which the solid is dissolved is: 65-70 ℃.
In still another aspect, the application also provides an application of the adhesive in the field of hydrogen fuel cells;
in some embodiments, the hydrogen fuel cell field includes the preparation of membrane electrodes.
In summary, the present application includes at least one of the following beneficial technical effects:
(1) The application provides an ultraviolet light curing adhesive which has better adhesive force, lower water absorption and better weather resistance for perfluorinated sulfonic acid resin films and PP and PE materials, and the adhesive can keep good peeling force and air tightness for a long time under high-temperature and high-humidity environments and realize batch automatic production.
(2) The ultraviolet light curing adhesive provided by the application is prepared by taking an acrylic ester monomer as a diluent, taking a thermoplastic elastomer as a main resin, taking tackifying resin as an adhesion promoter to improve the adhesion to a perfluorinated sulfonic acid resin film, PP and PE, adding a proper amount of thixotropic agent to enable the adhesive solution to have a certain thixotropic property, facilitating sizing, enabling gas-phase white carbon black to be dispersed more uniformly and stably through a silane coupling agent, and initiating curing through a photoinitiator.
Detailed Description
The technical solution of the present application is further illustrated by the following specific examples, which do not represent limitations on the scope of the present application. Some insubstantial modifications and adaptations of the application based on the inventive concept by others remain within the scope of the application.
Example 1 an ultraviolet light curing adhesive for Hydrogen Fuel cell Membrane electrode bonding
The composition formula of the embodiment is as follows: 10 parts of IBOA (isobornyl acrylate), 57 parts of PHEA (2-phenoxyethyl acrylate), 25 parts of SBS (block copolymer of styrene and butadiene), 8 parts of chlorinated polyolefin, 4 parts of 1-hydroxy-cyclohexyl-phenyl ketone, 2 parts of (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, 2 parts of fumed silica and 1.2 parts of gamma-methacryloxypropyl trimethoxysilane.
The preparation method of the embodiment comprises the following steps:
firstly, adding IBOA (isobornyl acrylate), PHEA (2-phenoxyethyl acrylate), SBS (block copolymer of styrene and butadiene) and chlorinated polyolefin into a kettle of a power mixer which is heated and can be vacuumized, and keeping the temperature at 65-70 ℃ to dissolve solids; stopping heating, adding 1-hydroxy-cyclohexyl-phenyl ketone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, gas-phase white carbon black and gamma-methacryloxypropyl trimethoxy silane, continuously stirring to completely dissolve the 1-hydroxy-cyclohexyl-phenyl ketone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, uniformly dispersing the gas-phase white carbon black, and finally carrying out vacuum defoaming to obtain the ultraviolet light curing adhesive. In the above preparation, attention was paid to light shielding after adding 1-hydroxy-cyclohexyl-phenyl-methanone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide.
Example 2 an ultraviolet light curing adhesive for Hydrogen Fuel cell Membrane electrode bonding
The composition formula of the embodiment is as follows: 10 parts of IBOA (isobornyl acrylate), 57 parts of PHEA (2-phenoxyethyl acrylate), 25 parts of SIS (styrene-isoprene block copolymer), 8 parts of chlorinated polyolefin, 4 parts of 1-hydroxy-cyclohexyl-phenyl ketone, 2 parts of (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, 2 parts of fumed silica and 1.2 parts of gamma-methacryloxypropyl trimethoxysilane.
The preparation method of the embodiment comprises the following steps: firstly, adding IBOA (isobornyl acrylate), PHEA (2-phenoxyethyl acrylate), SIS (styrene-isoprene segmented copolymer) and chlorinated polyolefin into a kettle of a power mixer which is heated and can be vacuumized, and keeping the temperature at 65-70 ℃ to dissolve solids; stopping heating, adding 1-hydroxy-cyclohexyl-phenyl ketone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, gas-phase white carbon black and gamma-methacryloxypropyl trimethoxy silane, continuously stirring, completely dissolving the 1-hydroxy-cyclohexyl-phenyl ketone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, uniformly dispersing the gas-phase white carbon black, and finally carrying out vacuum defoaming to obtain the ultraviolet light curing adhesive. In the above preparation, attention was paid to light shielding after adding 1-hydroxy-cyclohexyl-phenyl-methanone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide.
Example 3 an ultraviolet light curing adhesive for Hydrogen Fuel cell Membrane electrode bonding
The composition formula of the embodiment is as follows: 10 parts of IBOA (isobornyl acrylate), 57 parts of PHEA (2-phenoxyethyl acrylate), 25 parts of SIS (styrene-isoprene block copolymer), 8 parts of rosin resin, 4 parts of 1-hydroxy-cyclohexyl-phenyl ketone, 2 parts of (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, 2 parts of fumed silica and 1.2 parts of gamma-methacryloxypropyl trimethoxysilane.
The preparation method of the embodiment comprises the following steps: firstly, adding IBOA (isobornyl acrylate), PHEA (2-phenoxyethyl acrylate), SIS (styrene-isoprene block copolymer) and rosin resin into a kettle of a power mixer which is heated and can be vacuumized, and keeping the temperature at 65-70 ℃ to dissolve solids; stopping heating, adding 1-hydroxy-cyclohexyl-phenyl ketone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, gas-phase white carbon black and gamma-methacryloxypropyl trimethoxy silane, continuously stirring, completely dissolving the 1-hydroxy-cyclohexyl-phenyl ketone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, uniformly dispersing the gas-phase white carbon black, and finally carrying out vacuum defoaming to obtain the ultraviolet light curing adhesive. In the above preparation, attention was paid to light shielding after adding 1-hydroxy-cyclohexyl-phenyl-methanone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide.
Example 4 an ultraviolet light curing adhesive for Hydrogen Fuel cell Membrane electrode bonding
The composition formula of the embodiment is as follows: 10 parts of IBOA (isobornyl acrylate), 60 parts of PHEA (2-phenoxyethyl acrylate), 20 parts of SIS (styrene-isoprene block copolymer), 10 parts of chlorinated polyolefin, 4 parts of 1-hydroxy-cyclohexyl-phenyl ketone, 2 parts of (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, 2 parts of fumed silica and 1.2 parts of gamma-methacryloxypropyl trimethoxysilane.
The preparation method of the embodiment comprises the following steps: firstly, adding IBOA (isobornyl acrylate), PHEA (2-phenoxyethyl acrylate), SIS (styrene-isoprene segmented copolymer) and chlorinated polyolefin into a kettle of a power mixer which is heated and can be vacuumized, and keeping the temperature at 65-70 ℃ to dissolve solids; stopping heating, adding 1-hydroxy-cyclohexyl-phenyl ketone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, gas-phase white carbon black and gamma-methacryloxypropyl trimethoxy silane, continuously stirring, completely dissolving the 1-hydroxy-cyclohexyl-phenyl ketone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, uniformly dispersing the gas-phase white carbon black, and finally carrying out vacuum defoaming to obtain the ultraviolet light curing adhesive. In the above preparation, attention was paid to light shielding after adding 1-hydroxy-cyclohexyl-phenyl-methanone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide.
Example 5 an ultraviolet light curing adhesive for Hydrogen Fuel cell Membrane electrode bonding
The composition formula of the embodiment is as follows: 10 parts of IBOA (isobornyl acrylate), 57 parts of PHEA (2-phenoxyethyl acrylate), 10 parts of SBS (block copolymer of styrene and butadiene), 15 parts of SIS (styrene-isoprene block copolymer), 8 parts of rosin resin, 4 parts of 1-hydroxy-cyclohexyl-phenyl ketone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, 2 parts of gas-phase white carbon black and 1.2 parts of gamma-methacryloxypropyl trimethoxysilane.
The preparation method of the embodiment comprises the following steps: firstly, adding IBOA (isobornyl acrylate), PHEA (2-phenoxyethyl acrylate), SBS (block copolymer of styrene and butadiene), SIS (styrene-isoprene block copolymer) and rosin resin into a kettle of a power mixer which is provided with a heating and vacuumizing function, and keeping the temperature at 65-70 ℃ to dissolve solids; stopping heating, adding 1-hydroxy-cyclohexyl-phenyl ketone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, gas-phase white carbon black and gamma-methacryloxypropyl trimethoxy silane, continuously stirring, completely dissolving the 1-hydroxy-cyclohexyl-phenyl ketone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, uniformly dispersing the gas-phase white carbon black, and finally carrying out vacuum defoaming to obtain the ultraviolet light curing adhesive. In the above preparation, attention was paid to light shielding after adding 1-hydroxy-cyclohexyl-phenyl-methanone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide.
TABLE 1 formulation of the components of the above examples 1-5
Effect example 1
In order to further characterize the performance of the ultraviolet light curing adhesive prepared by the technical scheme provided by the application, the effect example is to measure the relevant performance of the ultraviolet light curing adhesive obtained in the above examples 1-5 respectively, and specifically comprises the following steps:
water absorption (%): curing the photo-curing adhesive into a sample with phi of 20 mm and 3mm, firstly baking the sample in an oven at 50 ℃ for 24 hours, taking out the sample, putting the sample into a dryer for cooling to room temperature, weighing the sample by an analytical balance and recording m 1 Decocting in boiling water for 2 hr, taking out, sucking surface water with filter paper, weighing with analytical balance, and recording m 2 The water absorption was (m) 2 -m 1 )/m 1 ％。
Peel strength (N/cm): the substrate was perfluorosulfonic acid resin film/PP, and the test sample was prepared and tested to test 180 degree peel strength according to GB/T2792-2014. The test of 'double 85, 168 hours' is that the sample prepared according to GB/T2792-2014 is put into a high temperature and high humidity box with 85 ℃ and 85% humidity, taken out after 168 hours and put into a constant temperature chamber with 25 ℃ for 24 hours, and 180-DEG peel strength is tested according to GB/T2792-2014.
The construction performance is as follows: the bonding of the electrode film is simulated, no flow occurs everywhere during the gluing, and bubbles are easy to be eliminated.
The relevant performance indexes of the adhesives of examples 1 to 5 obtained by the above method were as follows:
table 2 table of the relevant properties of the respective adhesives of examples 1 to 5
It can be seen from table 2 that the ultraviolet light curing adhesive prepared by using the thermoplastic elastomer as the main resin and using the tackifying resin as the adhesion promoter has good adhesion to the perfluorosulfonic acid resin film and the polyolefin film with low surface energy. For the adhesive, good air tightness is derived from good adhesiveness, the good adhesiveness is reflected in good peeling strength, the peeling strength obtained by the formula and the method provided by the embodiment of the application is basically unchanged after double 85 and 168 hours, which indicates that the adhesive provided by the application has high-temperature and high-humidity resistance and good adhesiveness, and the measured water absorption rate is very low after boiling in boiling water, which indicates that the boiling resistance is good. Therefore, according to the data in Table 2, it can be seen that the ultraviolet light curing adhesive provided by the application has better adhesion force, lower water absorption, better weather resistance and boiling resistance to perfluorinated sulfonic acid resin films and PP and PE materials, and can be used in high-temperature and high-humidity environments for a long time.
Comparative example 1
Based on example 1, this comparative example differs from example 1 in that: the components SBS (block copolymer of styrene and butadiene), chlorinated polyolefin in example 1 were replaced with urethane acrylate, the other conditions being kept identical, in particular as follows:
the composition formula of the comparative example is: 10 parts of IBOA (isobornyl acrylate), 57 parts of PHEA (2-phenoxyethyl acrylate), 33 parts of polyurethane acrylate, 4 parts of 1-hydroxy-cyclohexyl-phenyl ketone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, 2 parts of gas-phase white carbon black and 1.2 parts of gamma-methacryloxypropyl trimethoxysilane.
The preparation method comprises the following steps: firstly, adding IBOA (isobornyl acrylate), PHEA (2-phenoxyethyl acrylate) and polyurethane acrylate into a kettle of a power mixer which is heated and can be vacuumized, and keeping the temperature at 65-70 ℃ to dissolve solids; stopping heating, adding 1-hydroxy-cyclohexyl-phenyl ketone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, gas-phase white carbon black and gamma-methacryloxypropyl trimethoxy silane, continuously stirring to completely dissolve the 1-hydroxy-cyclohexyl-phenyl ketone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, uniformly dispersing the gas-phase white carbon black, and finally carrying out vacuum defoaming to obtain the ultraviolet light curing adhesive. In the above preparation, attention was paid to light shielding after adding 1-hydroxy-cyclohexyl-phenyl-methanone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide.
Comparative example 2
Based on example 1, this comparative example differs from example 1 in that: the consumption of the component gas phase white carbon black is 0 part, and other conditions are kept consistent, specifically as follows:
the composition formula of the comparative example is: 10 parts of IBOA (isobornyl acrylate), 57 parts of PHEA (2-phenoxyethyl acrylate), 25 parts of SBS (block copolymer of styrene and butadiene), 8 parts of chlorinated polyolefin, 4 parts of 1-hydroxy-cyclohexyl-phenyl ketone, 2 parts of (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, 0 part of fumed silica and 1.2 parts of gamma-methacryloxypropyl trimethoxysilane.
The preparation method comprises the following steps: firstly, adding IBOA (isobornyl acrylate), PHEA (2-phenoxyethyl acrylate), SBS (block copolymer of styrene and butadiene) and chlorinated polyolefin into a kettle of a power mixer which is heated and can be vacuumized, and keeping the temperature at 65-70 ℃ to dissolve solids; stopping heating, adding 1-hydroxy-cyclohexyl-phenyl ketone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide and gamma-methacryloxypropyl trimethoxy silane, continuously stirring to completely dissolve the 1-hydroxy-cyclohexyl-phenyl ketone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, and finally vacuum defoaming to obtain the ultraviolet light curing adhesive. In the above preparation, attention was paid to light shielding after adding 1-hydroxy-cyclohexyl-phenyl-methanone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide.
Comparative example 3
Based on example 1, this comparative example differs from example 1 in that: the consumption of the component gas phase white carbon black is 10 parts, and other conditions are kept consistent, specifically as follows:
the composition formula of the comparative example is: 10 parts of IBOA (isobornyl acrylate), 57 parts of PHEA (2-phenoxyethyl acrylate), 25 parts of SBS (block copolymer of styrene and butadiene), 8 parts of chlorinated polyolefin, 4 parts of 1-hydroxy-cyclohexyl-phenyl ketone, 2 parts of (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, 10 parts of gas-phase white carbon black and 1.2 parts of gamma-methacryloxypropyl trimethoxysilane.
The preparation method comprises the following steps: firstly, adding IBOA (isobornyl acrylate), PHEA (2-phenoxyethyl acrylate), SBS (block copolymer of styrene and butadiene) and chlorinated polyolefin into a kettle of a power mixer which is heated and can be vacuumized, and keeping the temperature at 65-70 ℃ to dissolve solids; stopping heating, adding 1-hydroxy-cyclohexyl-phenyl ketone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide and gamma-methacryloxypropyl trimethoxy silane, continuously stirring to completely dissolve the 1-hydroxy-cyclohexyl-phenyl ketone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, uniformly dispersing gas-phase white carbon black, and finally vacuum defoaming to obtain the ultraviolet light curing adhesive. In the above preparation, attention was paid to light shielding after adding 1-hydroxy-cyclohexyl-phenyl-methanone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide.
Comparative example 4
Based on example 1, this comparative example differs from example 1 in that: the amount of the chlorinated polyolefin component is 0 part, and other conditions are kept consistent, specifically as follows:
the composition formula of the comparative example is: 10 parts of IBOA (isobornyl acrylate), 57 parts of PHEA (2-phenoxyethyl acrylate), 25 parts of SBS (block copolymer of styrene and butadiene), 0 part of chlorinated polyolefin, 4 parts of 1-hydroxy-cyclohexyl-phenyl ketone, 2 parts of (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, 2 parts of fumed silica and 1.2 parts of gamma-methacryloxypropyl trimethoxysilane.
The preparation method comprises the following steps: firstly, adding IBOA (isobornyl acrylate), PHEA (2-phenoxyethyl acrylate) and SBS (block copolymer of styrene and butadiene) into a kettle of a power mixer which is heated and can be vacuumized, and keeping the temperature at 65-70 ℃ to dissolve solids; stopping heating, adding 1-hydroxy-cyclohexyl-phenyl ketone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide and gamma-methacryloxypropyl trimethoxy silane, continuously stirring to completely dissolve the 1-hydroxy-cyclohexyl-phenyl ketone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, uniformly dispersing gas-phase white carbon black, and finally vacuum defoaming to obtain the ultraviolet light curing adhesive. In the above preparation, attention was paid to light shielding after adding 1-hydroxy-cyclohexyl-phenyl-methanone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide.
Comparative example 5
Based on example 1, this comparative example differs from example 1 in that: the amount of the component SBS (block copolymer of styrene and butadiene) was 55 parts, the other conditions being kept identical, in particular as follows:
the composition formula of the comparative example is: 10 parts of IBOA (isobornyl acrylate), 57 parts of PHEA (2-phenoxyethyl acrylate), 55 parts of SBS (block copolymer of styrene and butadiene), 8 parts of chlorinated polyolefin, 4 parts of 1-hydroxy-cyclohexyl-phenyl ketone, 2 parts of (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, 2 parts of fumed silica and 1.2 parts of gamma-methacryloxypropyl trimethoxysilane.
The preparation method comprises the following steps: firstly, adding IBOA (isobornyl acrylate), PHEA (2-phenoxyethyl acrylate), SBS (block copolymer of styrene and butadiene) and chlorinated polyolefin into a kettle of a power mixer which is heated and can be vacuumized, and keeping the temperature at 65-70 ℃ to dissolve solids; stopping heating, adding 1-hydroxy-cyclohexyl-phenyl ketone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, gas-phase white carbon black and gamma-methacryloxypropyl trimethoxy silane, continuously stirring to completely dissolve the 1-hydroxy-cyclohexyl-phenyl ketone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, uniformly dispersing the gas-phase white carbon black, and finally carrying out vacuum defoaming to obtain the ultraviolet light curing adhesive. In the above preparation, attention was paid to light shielding after adding 1-hydroxy-cyclohexyl-phenyl-methanone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide.
Comparative example 6
Based on example 1, this comparative example differs from example 1 in that: the component SBS (block copolymer of styrene and butadiene) in example 1 was replaced with urethane acrylate, i.e., SBS (block copolymer of styrene and butadiene) 0 parts, urethane acrylate 25 parts, with the other conditions remaining the same, specifically as follows:
the composition formula of the comparative example is: 10 parts of IBOA (isobornyl acrylate), 57 parts of PHEA (2-phenoxyethyl acrylate), 0 part of SBS (block copolymer of styrene and butadiene), 25 parts of polyurethane acrylate, 8 parts of chlorinated polyolefin, 4 parts of 1-hydroxy-cyclohexyl-phenyl ketone, 2 parts of (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, 2 parts of gas-phase white carbon black and 1.2 parts of gamma-methacryloxypropyl trimethoxysilane.
The preparation method comprises the following steps: firstly, adding IBOA (isobornyl acrylate), PHEA (2-phenoxyethyl acrylate) and chlorinated polyolefin into a kettle of a power mixer which is heated and can be vacuumized, and keeping the temperature at 65-70 ℃ to dissolve solids; stopping heating, adding polyurethane acrylic ester, 1-hydroxy-cyclohexyl-phenyl ketone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide and gamma-methacryloxypropyl trimethoxy silane, continuously stirring to completely dissolve the 1-hydroxy-cyclohexyl-phenyl ketone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, uniformly mixing all materials, adding gas phase white carbon black, continuously stirring to uniformly disperse the gas phase white carbon black, and finally performing vacuum defoaming to obtain the ultraviolet light curing adhesive. In the above preparation, attention was paid to light shielding after adding 1-hydroxy-cyclohexyl-phenyl-methanone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide.
Table 3 the component formulations of the above comparative examples 1-6:
effect example 2
The results of further measuring the properties of the uv curable adhesives obtained in comparative examples 1 to 6 according to the method of measuring the properties of each uv curable adhesive obtained in examples 1 to 5 in effect example 1 are shown in table 2, and are specifically as follows:
TABLE 4 Table of the relevant Properties of the adhesives of example 1 and comparative examples 1-6
It can be seen from table 4 that the photo-curing adhesive using the general urethane acrylate prepolymer as the main resin has poor adhesion to two substrates, and even if the adhesion of the tackifying resin is improved, the adhesion is far lower than that of the adhesive obtained in the embodiment of the application, and the water absorption is high, the water boiling resistance is poor, and the peeling force is seriously reduced after high temperature and high humidity. Secondly, in the adhesive formulation provided by the application, the amount of thixotropic agent is also critical and plays a critical role in the properties of the final adhesive, such as: when the dosage of the thixotropic agent is 0, the thixotropic agent has no thixotropy, has good fluidity, can flow when being coated with glue, and when the dosage of the thixotropic agent is too much, the viscosity and the thixotropy are too large, so that the glue cannot be coated; in addition, experiments prove that in the adhesive formula system provided by the application, because the acrylate monomer has limited solubility on the thermoplastic elastomer, the adhesive with better performance in all aspects is wanted to be obtained, and the dosage of the thermoplastic elastomer is also critical.
It will be understood that the application has been described in terms of several embodiments, and that various changes and equivalents may be made to these features and embodiments by those skilled in the art without departing from the spirit and scope of the application. In addition, many modifications may be made to adapt a particular situation or material to the teachings of the application without departing from the essential scope thereof. Therefore, it is intended that the application not be limited to the particular embodiment disclosed, but that the application will include all embodiments falling within the scope of the appended claims.

Claims (10)

1. The ultraviolet light curing adhesive is characterized by comprising the following components: acrylic monomer, thermoplastic elastomer, tackifying resin, photoinitiator, thixotropic agent and silane coupling agent;
wherein the adhesive uses the thermoplastic elastomer as a main resin.
2. The adhesive of claim 1, comprising the following components in parts by weight: 20-85 parts of acrylic acid monomer, 10-55 parts of thermoplastic elastomer, 5-25 parts of tackifying resin, 1-15 parts of photoinitiator, 1-10 parts of thixotropic agent and 0.1-8 parts of silane coupling agent;
preferably, the composition comprises the following components in parts by weight: 30-80 parts of acrylic acid monomer, 10-50 parts of thermoplastic elastomer, 5-20 parts of tackifying resin, 1-10 parts of photoinitiator, 1-9 parts of thixotropic agent and 0.5-7 parts of silane coupling agent.
3. The adhesive of any of claims 1-2, wherein the acrylate monomer is selected from one or more of a monofunctional acrylate, a difunctional acrylate, a polyfunctional acrylate;
preferably, the mono-functional acrylate is selected from one or more of methyl acrylate, ethyl acrylate, isobornyl acrylate, tetrahydrofuran acrylate, cyclotrimethylol propane methylacrylate, 2-phenoxyethyl acrylate, 4-tert-butylcyclohexyl acrylate, benzyl acrylate and 3, 5-trimethylcyclohexane acrylate;
preferably, the difunctional acrylate is selected from one or more of 1, 6-hexanediol diacrylate, dipropylene glycol diacrylate, pentanediol diacrylate, tricyclodecane dimethanol diacrylate;
preferably, the multifunctional acrylate is selected from one or more of trimethylolpropane triacrylate, ethoxylated trimethylolpropane triacrylate, propoxylated trimethylolpropane triacrylate, pentaerythritol triallyl ether, tris (2-hydroxyethyl) isocyanuric acid triacrylate, and dipentaerythritol pentaacrylate;
preferably, the acrylate monomer is selected from the group consisting of isobornyl acrylate in combination with 2-phenoxyethyl acrylate; preferably, the weight ratio of the isobornyl acrylate to the 2-phenoxyethyl acrylate is 5-15:45-65; preferably, the weight ratio of the isobornyl acrylate to the 2-phenoxyethyl acrylate is 8-12:50-60.
4. The adhesive of any one of claims 1-2, wherein the thermoplastic elastomer is selected from one or more of SBS, SIS, SEBS, SEPS; preferably, the thermoplastic elastomer is selected from SBS and/or SIS; preferably, the combined weight ratio of SBS to SIS in the thermoplastic elastomer is 5-15:10-20; preferably, the combined weight ratio of SBS to SIS in the thermoplastic elastomer is 8-12:12-18.
5. The adhesive of any of claims 1-2, wherein the tackifying resin is selected from one or more of terpene resins, petroleum resins, hydrogenated petroleum resins, chlorinated polyolefins, rosin resins, hydrogenated rosin resins; preferably, the tackifying resin is selected from chlorinated polyolefin or rosin resins.
6. The adhesive of any one of claims 1-2, wherein the photoinitiator is selected from one or more of 2-hydroxy-2-methyl-1-phenyl ketone, 1-hydroxy-cyclohexyl-phenyl ketone, benzophenone, benzoin methyl ether, benzoin ethyl ether, benzoin butyl ether, a-dimethoxy-a-phenylacetophenone, (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, ethyl 2,4, 6-trimethylbenzoyl phenyl phosphonate, 2-methyl-1- [ 4-methylthiophenyl ] -2-morpholino-1-propanone, 2-isopropylthiazone ketone (2, 4 isomer mixture), 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone, and the like; preferably, the photoinitiator is selected from the group consisting of 1-hydroxy-cyclohexyl-phenyl-methanone and (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide; preferably, the combined weight ratio of the 1-hydroxy-cyclohexyl-phenyl ketone and the (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide is: 2-8:1-5; preferably, the combined weight ratio of the 1-hydroxy-cyclohexyl-phenyl ketone and the (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide is 3-5:1-4.
7. The adhesive of any one of claims 1-2, wherein the thixotropic agent is selected from one or more of fumed silica, polyamide wax, hydrogenated castor oil; preferably, the thixotropic agent is selected from fumed silica.
8. The adhesive of any of claims 1-2, wherein the silane coupling agent is selected from one or more of vinyl trimethoxysilane, vinyl triethoxysilane, gamma-aminopropyl triethoxysilane, gamma-glycidoxypropyl trimethoxysilane, gamma-methacryloxypropyl trimethoxysilane, N- (beta-aminoethyl) -gamma-aminopropyl trimethylethoxysilane; preferably, the silane coupling agent is selected from gamma-methacryloxypropyl trimethoxysilane.
9. A method of preparing an adhesive according to any one of claims 1 to 8, comprising the steps of:
(1) Adding acrylic acid monomer, thermoplastic elastomer and tackifying resin into a kettle of a power mixer which is heated and can be vacuumized, and heating to dissolve solids;
(2) After the solid is dissolved, stopping heating, adding the photoinitiator, the thixotropic agent and the silane coupling agent, keeping away from light, continuously stirring to completely dissolve the photoinitiator, uniformly dispersing the thixotropic agent, and finally carrying out vacuum defoamation to obtain the ultraviolet light curing adhesive;
preferably, in the step (1), the heating temperature for dissolving the solid is: 65-70 ℃.
10. Use of the adhesive according to any one of claims 1-8 in the field of hydrogen fuel cells;
preferably, the hydrogen fuel cell field includes the preparation of membrane electrodes.
CN202310197769.6A 2023-02-27 2023-02-27 Ultraviolet light curing adhesive for bonding membrane electrode of hydrogen fuel cell Active CN117106394B (en)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140343186A1 (en) * 2011-12-19 2014-11-20 darbond technology co., ltd Ultraviolet cured optic binder
CN107987760A (en) * 2017-11-15 2018-05-04 江门保实捷化工有限公司 A kind of novel environment friendly adhesive and its preparation method and application
CN112358835A (en) * 2020-11-04 2021-02-12 苏州赛伍应用技术股份有限公司 Adhesive composition, easy-to-pull adhesive tape and preparation method and application thereof
CN112852309A (en) * 2021-02-24 2021-05-28 东莞市博翔电子材料有限公司 Adhesive for power battery aluminum plastic film and processing technology thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140343186A1 (en) * 2011-12-19 2014-11-20 darbond technology co., ltd Ultraviolet cured optic binder
CN107987760A (en) * 2017-11-15 2018-05-04 江门保实捷化工有限公司 A kind of novel environment friendly adhesive and its preparation method and application
CN112358835A (en) * 2020-11-04 2021-02-12 苏州赛伍应用技术股份有限公司 Adhesive composition, easy-to-pull adhesive tape and preparation method and application thereof
CN112852309A (en) * 2021-02-24 2021-05-28 东莞市博翔电子材料有限公司 Adhesive for power battery aluminum plastic film and processing technology thereof

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