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CN112795347A - Ultraviolet light and moisture curable adhesive and preparation method thereof - Google Patents

Ultraviolet light and moisture curable adhesive and preparation method thereof Download PDF

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Publication number
CN112795347A
CN112795347A CN202110046542.2A CN202110046542A CN112795347A CN 112795347 A CN112795347 A CN 112795347A CN 202110046542 A CN202110046542 A CN 202110046542A CN 112795347 A CN112795347 A CN 112795347A
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Prior art keywords
stirring
moisture
acrylate
curable adhesive
silane
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Pending
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CN202110046542.2A
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Chinese (zh)
Inventor
黎达华
张银华
史襄桥
章锋
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Guangzhou Huitian New Material Co ltd
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Guangzhou Huitian New Material Co ltd
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Priority to CN202110046542.2A priority Critical patent/CN112795347A/en
Publication of CN112795347A publication Critical patent/CN112795347A/en
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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
    • C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
    • 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
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

The invention discloses an ultraviolet and moisture curable adhesive and a preparation method thereof, wherein the adhesive comprises the following components in parts by mass: 20-60% of silane-terminated oligomer, 10-40% of polyurethane acrylate oligomer, 5-40% of acrylate monomer, 0.5-5% of silane coupling agent, 0.5-5% of free radical photoinitiator and 0.5-5% of photoacid generator. The introduction of the photo-acid generator enables the ultraviolet light and moisture curing adhesive to have good storage stability, the silane-terminated polymer enables the adhesive composition to have good mechanical properties after being cured, and the adhesive composition has high and low temperature and high humidity resistance reliability, is not easy to crack due to colloid under the action of environmental stress, can be rapidly cured after being irradiated by ultraviolet light, has a good positioning effect on the bonding of a camera window, meets the requirement of a continuous and rapid production and assembly process, is integrally good in bonding strength after moisture curing is completed, and has excellent reliability.

Description

Ultraviolet light and moisture curable adhesive and preparation method thereof
Technical Field
The invention relates to the field of curing adhesion, in particular to an ultraviolet and moisture curable adhesive and a preparation method thereof.
Background
At present, in many electronic industry fields, such as the manufacture of security cameras, adhesives are generally used for bonding substrates and components such as plastics, glass, coated metals and the like. The security protection camera equipment requires that there is not atomizing, no steam in the long-term use in camera window, lens, the safety cover internal surface, and the dust infiltration, otherwise greatly influence the shooting effect of security protection camera lens. Most of the existing camera assembly and sealing use UV glue (ultraviolet light curing adhesive), and the existing camera assembly and sealing have the advantages of high curing speed, high assembly rhythm and high environmental protection property. However, due to the complex and special design and the opaque base parts such as glass fiber reinforced plastics, metals and the like, the ultraviolet radiation generated in the process of assembling the base parts with the lenses cannot reach the dark areas effectively, so that the conventional ultraviolet-curable adhesive cannot meet the requirements of actual production and application.
In addition, outdoor security protection camera is because of often being in the state that the sun is drenched with rain, and UV glues in the use, often exists through the cold and hot alternation of a period, produces stress concentration, and long-term accumulation can lead to sealed bonding inefficacy. The invasion of water vapor and dust into the interior of the camera cavity results in the reduction of the use quality and the service life of the camera.
The reactive alkoxysilane group-containing polymer undergoes condensation polymerization when contacted with moisture, and is an adhesive system having elasticity and capable of reducing the build-up of thermal cycling stress. Furthermore, adhesives based on alkoxysilane-crosslinked polymers exhibit, in their cured state, not only good adhesion properties to some substrates, in particular glass-metal substrates, but also very good mechanical properties. The prior art compositions based on silane-functional polymers generally have a low curing speed at room temperature under the action of moisture, and must be supplemented with basic, acidic or metal-containing catalysts, which, however, also limit the workability of the adhesive application and reduce the storage and use stability of the system.
Disclosure of Invention
The invention aims to provide an ultraviolet light and moisture curable adhesive and a preparation method thereof, so as to solve the problems in the background technology.
In order to achieve the purpose, the invention provides the following technical scheme: an ultraviolet light and moisture curable adhesive and a preparation method thereof, comprising the following components by mass:
20-60% of silane-terminated oligomer, 10-40% of polyurethane acrylate oligomer, 5-40% of acrylate monomer, 0.5-5% of silane coupling agent, 0.5-5% of free radical photoinitiator and 0.5-5% of photoacid generator.
Preferably, the silane terminated oligomer may be one or more of polyether polyurethane terminated at both ends with siloxane groups, polyether terminated at both ends with siloxane groups, and polyacrylate copolymer.
Preferably, the urethane acrylate oligomer is one of polyether urethane acrylate, polyester urethane acrylate and polybutadiene urethane acrylate.
Preferably, the silane coupling agent may be one or more of vinyltriethoxysilane, gamma- (2, 3-glycidoxy) propyltrimethoxysilane, gamma- (methacryloyloxy) propyltrimethoxysilane, vinyltrimethoxysilane and the like.
Preferably, the photoinitiator is used for crosslinking functional groups of the acrylate oligomer and the acrylate monomer, and the photoinitiator is one or more of benzoin ethers, alpha-hydroxyketone derivatives, alpha-aminoketone derivatives, benzil and derivatives thereof, and acylphosphine peroxide.
Preferably, the preparation method of the ultraviolet light and moisture curable adhesive comprises the following steps:
firstly preparing raw materials according to the proportion, putting the raw materials into a stirring kettle for stirring, then putting raw materials of urethane acrylate 3641AA, isobornyl acrylate and N, N-dimethylacrylamide into the kettle for pre-stirring after sampling and weighing, controlling the temperature at 40-50 ℃, setting the stirring speed at 50-70rpm, and the stirring time at 50-70 minutes, then putting SAX350 into the kettle for continuous stirring, setting the stirring speed at 110-130rpm, and the stirring time at 50-70 minutes, then adding 1173, TPO, 250 and VTMO into the kettle after weighing, setting the stirring speed at 110-130rpm, and the stirring time at 25-35 minutes, vacuumizing the obtained mixture in a vacuum stirring kettle, setting the vacuum degree at-0.1 MPa, the stirring speed at 110-130rpm, and the stirring time at 25-35 minutes, and after stirring, filtering the uniformly mixed mixture, and putting the mixture into a moisture-proof package for sealed storage.
The invention has the technical effects and advantages that: a novel UV and moisture curable adhesive composition is provided comprising an alkoxysilane polymer and a urethane acrylate, wherein the reactive alkoxysilane based polymer system undergoes a condensation reaction when exposed to water or moisture to form a polymer having good mechanical properties and elasticity. Has good adhesion to glass, metal and plastic, strong interfacial action, and excellent reliability under high-low temperature and high-humidity environments. The problem that the camera loses effectiveness due to the stress action in the long-term outdoor use process can be avoided;
the present invention is achieved by providing compositions based on siloxane-containing capped polymers and photoacid generators, urethane acrylate oligomers, acrylate monomers, coupling agents, and the like, without the addition of other catalysts for moisture curing alkoxysilanes.
The composition remains liquid for at least 24 hours even in the presence of moisture and cures only after exposure to ultraviolet light, and has a high initial bond strength after curing. Can satisfy camera window lens sealing bonding strength.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The invention provides an ultraviolet and moisture curable adhesive and a preparation method thereof, wherein the adhesive comprises the following components in parts by mass:
20-60% of silane-terminated oligomer, 10-40% of polyurethane acrylate oligomer, 5-40% of acrylate monomer, 0.5-5% of silane coupling agent, 0.5-5% of free radical photoinitiator and 0.5-5% of photoacid generator;
the silane-terminated oligomer is an oligomer having a siloxane group at a molecular terminal, and having at least one or more alkoxy groups bonded to a silicon atom at a molecular terminal. The two ends of the molecular chain can be both siloxane groups, or the siloxane groups can be only arranged at one end, and the other end can be other functional groups, such as (methyl) acrylate groups, ester groups and the like.
The reactive alkoxysilane group-containing polymer undergoes condensation polymerization when contacted with moisture, and is an adhesive system having elasticity and capable of reducing the build-up of thermal cycling stress. Furthermore, adhesives based on alkoxysilane-crosslinked polymers exhibit, in their cured state, not only good adhesion properties to some substrates, in particular glass-metal substrates, but also very good mechanical properties.
The silane terminated oligomer can be one or more of polyether polyurethane with both ends terminated by siloxane groups, polyether with both ends terminated by siloxane groups and polyacrylate copolymer.
The silane-terminated oligomer used in the present invention may be selected from SAX350, SAX750, MA451, MAX602, and the like, available from KANEKA, Japan; GENIOSIL series products GENIOSILSTP-E10 and GENIOSILSTP-E35 from wacker corporation.
The polyurethane acrylate oligomer is one of polyether polyurethane acrylate, polyester polyurethane acrylate and polybutadiene polyurethane acrylate. Polyether urethane acrylates are preferred due to compatibility issues with the silane terminated oligomers. The adhesive composition is mainly endowed with good initial bonding strength and high and low temperature resistance after being irradiated by ultraviolet light.
The urethane acrylate oligomer used in the present invention may be selected from CN8004, supplied by sandomar, 3641AA, 3641AJ, 3747AE, 3741AJ, and the like, supplied by demander.
The acrylate monomer is not particularly limited, and may be a monofunctional acrylate monomer, i.e., having one acrylate group in the molecule, or a multifunctional acrylate monomer, i.e., having two or more acrylate functional groups.
The monofunctional acrylate monomer includes, for example, 2-hydroxyethyl acrylate, isobornyl acrylate, lauryl acrylate, acryloylmorpholine, phenoxyethyl acrylate, N-dimethylacrylamide, tetrahydrofurfuryl acrylate, dicyclopentenyloxy acrylate, cyclotrimethylolpropane formal acrylate, 4-t-butylcyclohexyl acrylate, and the like.
The multifunctional acrylate monomer includes, for example, 1, 4-butanediol diacrylate, tricyclodecane dimethanol diacrylate, trimethylolpropane triacrylate, polyethylene glycol diacrylate, etc
These monofunctional acrylate monomer and polyfunctional acrylate monomer may be used alone or in combination of two or more monomers, or the monofunctional and polyfunctional monomers may be used in combination.
In a preferred embodiment of the present invention, the acrylate monomer is isobornyl acrylate, N-dimethylacrylamide or a combination thereof, and a combination of isobornyl acrylate and N, N-dimethylacrylamide is more preferred.
The silane coupling agents do not include those capable of acting as alkoxy condensation crosslinking catalysts in the presence of moisture and thereby catalyzing the curing of the composition, such as aminosilane coupling agents.
The silane coupling agent can be one or more of coupling agents such as vinyl triethoxysilane, gamma- (2, 3-epoxypropoxy) propyl trimethoxysilane, gamma- (methyl acryloyl oxygen) propyl trimethoxysilane and vinyl trimethoxysilane.
In a preferred embodiment of the present invention, the silane coupling agent is selected from VTMOA-171 from Meiji.
Photoinitiators are generally used to initiate photopolymerization of unsaturated monomers or oligomers. In the present invention, the photoinitiator is used to crosslink the functional groups of the acrylate oligomer and the acrylate monomer.
The photoinitiator is one or more of benzoin ethers, alpha-hydroxy ketone derivatives, alpha-amino ketone derivatives, benzil and derivatives thereof, and acyl phosphine peroxide. They may be used alone or in combination.
In a preferred embodiment of the invention, the photo radical initiator is a combination selected from 1173 and TPO from Ciba.
A photoacid generator is a compound that can be activated to release a strong acid by exposure to light radiation. The released acid catalyzes the hydrolysis and crosslinking of the moisture-curable groups contained in the above-described composition.
The adhesive composition does not contain any other catalyst for moisture curing, except for the photoacid generator. In particular, the explicit tablets exclude the use of catalysts based on organotin compounds or aminosilanes, which are commonly used in the prior art.
The photoacid generator may be an initiator for cationic curing, such as an arylsulfonium salt or an aryliodonium salt.
As the commercially available aryl sulfonium salt photoinitiator as the photoacid generator, UVI-6976, UVI-6974 and the like from the Dow chemical company can be mentioned
Commercially available aryliodonium salt photoinitiators as photoacid generators may be Irgacure250 from Pasteur, Rhodorsil2074 from Rhodia, and the like.
In a preferred embodiment of the invention, the photoacid generator is a cationic initiator belonging to the class of aryliodonium salts, selected from Irgacure250 from basf.
The method for testing the sealing and bonding airtightness of the camera lens comprises the following steps: and uniformly coating the adhesive into a glue dispensing groove of a cast aluminum metal lens base with a polyester coating, and covering a glass lens. The sample was then placed in a UV mercury lamp curing oven at 3000mJ/cm2And (5) energy curing, and finally assembling the camera sample piece and the back plastic cavity. Followed by high temperature and high humidity (85 ℃, 85 RH%) and high low temperature cycling (-40 ℃ x 1h, 80 ℃ x 1h, switching time 15 minutes, all as one cycle) aging tests. Most preferablyAnd (3) verifying the air tightness of the sealed bonding of the camera window and the glass lens: and completely immersing the assembled sample piece in water at 25 ℃, applying air with the pressure of 0.05MPa to the cavity in the camera sample piece by using the air pipe connector, observing whether bubbles are generated in the water, and if the bubbles are not generated, indicating that the air tightness test is passed, otherwise, not passing the air tightness test.
The method for testing the bonding strength of the glass and the PC comprises the following steps: the prepared adhesive is dotted on the lapping surface of a PC sheet with the thickness of 25mm multiplied by 100mm multiplied by 2mm through a needle cylinder, a glass sheet with the thickness of 25mm multiplied by 100mm multiplied by 2mm is lapped on the PC sheet, the lapping area is 12.5mm multiplied by 25mm, and the glue layer thickness is 0.2 mm. Then irradiating with ultraviolet light of 1000W UV mercury lamp with irradiation energy of 3000mJ/cm2. And then, carrying out tensile-shear strength test on the sample strip on an equipment universal electronic tensile machine, wherein the tensile speed is 10mm/min, and recording the test result.
Viscosity test method: the viscosities of the gum samples at 10rpm were tested according to GB/T2794 at 25. + -. 1 ℃ by a Brookfield DV-II + Pro rotational viscometer using a s51 spindle. And the adhesive compositions are considered to be storage stable with less than 100% increase in viscosity under the storage conditions.
Table 1: ingredient ratio table of examples and comparative examples
Figure BDA0002897490780000071
Figure BDA0002897490780000081
SAX 350: MS polymers (silane modified polyethers) provided by KANEKA corporation of japan.
MAX 602: acrylic resin modified MS polymers provided by KANEKA, Japan.
3641 AA: DYMAX provides polyether urethane acrylate oligomers.
EB 8413: urethane acrylate oligomers are available from Zhanxin corporation.
IBOA: isobornyl acrylate.
DMAA: n, N-dimethylacrylamide.
VTMO: vinyl trimethoxy silane.
KH 550: gamma-aminopropyltriethoxysilane.
KH 570: gamma-methacryloxypropyltrimethoxysilane.
1173: 2-hydroxy-2-methyl-1-phenyl-1-propanone.
TPO: diphenyl- (2,4, 6-trimethylbenzoyl) oxyphosphorus.
250: IRGACURE250, 4-isobutylphenyl-4' -methylphenyliodium hexafluorophosphate, supplied by BASF corporation.
DBTL: dibutyltin dilaurate.
Table 2: performance test results for UV and moisture curable adhesives
Figure BDA0002897490780000091
Figure BDA0002897490780000101
Note: CF is cohesive failure; MF is mixed destruction; AF is an interface destruction.
OK ═ viscosity increase < 100%, meeting storage stability criteria, NG ═ viscosity increase > 100%, failing storage stability criteria.
In table 2, the comparative examples and comparative examples can find that very small amounts of photoacid generated are sufficient to achieve subsequent moisture full cure. Even in the presence of moisture, the adhesive can be maintained for at least 7 days after dispensing, can not be cured as long as the adhesive is not irradiated by ultraviolet light, and has good dispensing operability and use stability.
In the aspect of adhesive property, compared with the traditional organic metal compound catalyzed moisture curing adhesive (such as a comparative example 1), the composition in the embodiment has good adhesive strength immediately after being irradiated by ultraviolet light, has good positioning effect on the camera window adhesion, and can well meet the requirement of a rapid, continuous and mass assembly production process thereof. In addition, after the ultraviolet light is irradiated and the moisture is cured for 1 day, the strength of the adhesive can meet the air tightness test of the sealing and bonding of the camera sample piece. After moisture curing for 7 days, the adhesive is basically and completely cured, and the overall bonding performance reaches the maximum.
Compared with a single ultraviolet curing adhesive (comparative example 2), the introduction of the silane functional polymer can well improve the high-low temperature resistance, high-temperature high-humidity resistance and adhesion to metal glass, PC and other plastics of the adhesive combination, and enhance the interface effect. Therefore, the camera window bonding device has a good sealing bonding effect.
Therefore, after the adhesive is used for a long time, the adhesive can withstand the influence of outdoor damp and heat and temperature alternation complex environmental conditions, cannot cause the sealing failure of a camera window, can solve the bonding and sealing problem of a high-definition outdoor security lens, has strong bonding capability, and is suitable for popularization and application.
The introduction of the photo-acid generator in the invention ensures that the ultraviolet light and moisture curing adhesive has good storage stability, and the silane-terminated polymer ensures that the adhesive composition has good mechanical property after curing, high and low temperature and high humidity reliability, and is not easy to generate colloid cracking under the action of environmental stress.
Can solidify rapidly after shining through the ultraviolet ray, bond to the camera window and have fine locate function, satisfy quick production assembly process in succession, later stage moisture solidification is accomplished, wholly has good adhesive strength, has excellent reliability.
Compared to the prior art, very low photoacid generator concentrations have been shown to be sufficient to achieve rapid skin formation and subsequent full cure. This is one of the advantages in view of the high cost of the corresponding photoacid generators. In addition, no other acidic, basic or metal-containing moisture curing catalysts are contained, except for a small amount of photoacid generator. In addition to the good improvement of the storage stability of the composition, it also allows for longer working times in humid environments.
Finally, it should be noted that: although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that modifications may be made to the embodiments or portions thereof without departing from the spirit and scope of the invention.

Claims (6)

1. The ultraviolet light and moisture curable adhesive is characterized by comprising the following components in parts by mass:
20-60% of silane-terminated oligomer, 10-40% of polyurethane acrylate oligomer, 5-40% of acrylate monomer, 0.5-5% of silane coupling agent, 0.5-5% of free radical photoinitiator and 0.5-5% of photoacid generator.
2. The UV-and moisture-curable adhesive according to claim 1, wherein the silane-terminated oligomer is one or more selected from the group consisting of polyether urethane terminated at both ends with siloxane groups, polyether terminated at both ends with siloxane groups, and polyacrylate copolymer.
3. The uv and moisture curable adhesive according to claim 1, wherein the urethane acrylate oligomer is one of polyether urethane acrylate, polyester urethane acrylate, and polybutadiene urethane acrylate.
4. The UV-and moisture-curable adhesive according to claim 1, wherein the silane coupling agent is one or more of vinyltriethoxysilane, gamma- (2, 3-glycidoxy) propyltrimethoxysilane, gamma- (methacryloyloxy) propyltrimethoxysilane, vinyltrimethoxysilane, etc.
5. The UV-and moisture-curable adhesive according to claim 1, wherein the photoinitiator is used for crosslinking functional groups of the acrylate oligomer and the acrylate monomer, and the photoinitiator is one or more of benzoin ethers, α -hydroxy ketone derivatives, α -amino ketone derivatives, benzil and derivatives thereof, and acylphosphine peroxide.
6. A preparation method of an ultraviolet light and moisture curable adhesive is characterized by comprising the following steps:
firstly preparing raw materials according to the proportion, putting the raw materials into a stirring kettle for stirring, then putting raw materials of urethane acrylate 3641AA, isobornyl acrylate and N, N-dimethylacrylamide into the kettle for pre-stirring after sampling and weighing, controlling the temperature at 40-50 ℃, setting the stirring speed at 50-70rpm, and the stirring time at 50-70 minutes, then putting SAX350 into the kettle for continuous stirring, setting the stirring speed at 110-130rpm, and the stirring time at 50-70 minutes, then adding 1173, TPO, 250 and VTMO into the kettle after weighing, setting the stirring speed at 110-130rpm, and the stirring time at 25-35 minutes, vacuumizing the obtained mixture in a vacuum stirring kettle, setting the vacuum degree at-0.1 MPa, the stirring speed at 110-130rpm, and the stirring time at 25-35 minutes, and after stirring, filtering the uniformly mixed mixture, and putting the mixture into a moisture-proof package for sealed storage.
CN202110046542.2A 2021-01-14 2021-01-14 Ultraviolet light and moisture curable adhesive and preparation method thereof Pending CN112795347A (en)

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Cited By (3)

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Publication number Priority date Publication date Assignee Title
CN114395361A (en) * 2021-12-20 2022-04-26 杭州之江有机硅化工有限公司 UV (ultraviolet) photocuring composition and application thereof
WO2022271590A1 (en) * 2021-06-22 2022-12-29 Dow Silicones Corporation Dual curable silicone composition
CN115807224A (en) * 2022-11-30 2023-03-17 湖北回天新材料股份有限公司 Metal surface composite treating agent and preparation method and application thereof

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CN103173137A (en) * 2011-12-22 2013-06-26 汉高股份有限公司 Ultraviolet-curable and moisture-curable adhesive composition
US20140242322A1 (en) * 2011-07-22 2014-08-28 H.B. Fuller Company One component, dual-cure adhesive for use in electronics
US20220033697A1 (en) * 2018-11-08 2022-02-03 Delo Industrie Klebstoffe Gmbh & Co. Kgaa Moisture-curable one-pack composition and method for joining, casting and coating using the composition

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140242322A1 (en) * 2011-07-22 2014-08-28 H.B. Fuller Company One component, dual-cure adhesive for use in electronics
CN103173137A (en) * 2011-12-22 2013-06-26 汉高股份有限公司 Ultraviolet-curable and moisture-curable adhesive composition
US20140303272A1 (en) * 2011-12-22 2014-10-09 Henkel (China) Company Limited An ultra-violet-curable and moisture-curable adhesive composition
US20220033697A1 (en) * 2018-11-08 2022-02-03 Delo Industrie Klebstoffe Gmbh & Co. Kgaa Moisture-curable one-pack composition and method for joining, casting and coating using the composition

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022271590A1 (en) * 2021-06-22 2022-12-29 Dow Silicones Corporation Dual curable silicone composition
CN114395361A (en) * 2021-12-20 2022-04-26 杭州之江有机硅化工有限公司 UV (ultraviolet) photocuring composition and application thereof
CN114395361B (en) * 2021-12-20 2023-04-14 杭州之江有机硅化工有限公司 UV (ultraviolet) photocuring composition and application thereof
CN115807224A (en) * 2022-11-30 2023-03-17 湖北回天新材料股份有限公司 Metal surface composite treating agent and preparation method and application thereof

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Application publication date: 20210514