CN109651961A - A kind of acrylate pressure sensitive adhesive, photo-thermal dual curable glue film and preparation method thereof - Google Patents
A kind of acrylate pressure sensitive adhesive, photo-thermal dual curable glue film and preparation method thereof Download PDFInfo
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- CN109651961A CN109651961A CN201811500024.8A CN201811500024A CN109651961A CN 109651961 A CN109651961 A CN 109651961A CN 201811500024 A CN201811500024 A CN 201811500024A CN 109651961 A CN109651961 A CN 109651961A
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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
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
-
- 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
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
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- 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
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
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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
- C09J7/10—Adhesives in the form of films or foils without carriers
-
- 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
- C09J7/38—Pressure-sensitive adhesives [PSA]
- C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C09J7/385—Acrylic polymers
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- 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
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
- C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/302—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention discloses a kind of acrylate pressure sensitive adhesives, it is 100:(20~50 by weight ratio): (30~50): (0.5~3.0): polyacrylate performed polymer, reactive diluent, organic solvent, photoinitiator and the crosslinking agent of (0.3~3.0), which are uniformly mixed, to be made, polyacrylate performed polymer is to dissolve butyl acrylate, methyl methacrylate, glycidyl methacrylate in organic solvent, and initiator is added, it is being passed through N2Under conditions of react be made；The invention also discloses a kind of photo-thermal dual curable glue films, including the use of adhesive layer prepared by above-mentioned acrylate pressure sensitive adhesive, and carry out photo-thermal crosslinking Treatment to it；The invention also discloses the preparation methods of above-mentioned photo-thermal dual curable glue film.Photo-thermal dual curable glue film prepared by the present invention has high-adhesion, preferably doing over again property, and can be realized photo-thermal dual curable, shortens curing time, improves production efficiency.
Description
Technical field
The present invention relates to electronics adhesive technology field more particularly to a kind of acrylate pressure sensitive adhesives, photo-thermal dual curable glue film
And preparation method thereof.
Background technique
With electronics, the fast development of communications industry, various electronic equipments, such as mobile phone, computer, TV, navigator and pen
Remember that the volume of this grade is more and more small, is intended to multifunction, lighting and highly integrated development, in order to meet the development trend,
It needs for multiple components of electronic equipment to be combined, especially be glued between each small parts of electronic equipment internal
Knot.
The bonding of each small parts of electronic equipment internal mainly uses ultra-thin PET double faced adhesive tape, electronics glue spots at present
Adhesive process and pressure-sensitive adhesive connection technology.
Using ultra-thin PET double faced adhesive tape bond when there are adhesion strengths it is low, doing over again property is poor the disadvantages of；
Although electronics glue spots adhesive process is it is possible to prevente effectively from the low problem of adhesion strength, doing over again property is poor, sets simultaneously
Standby investment is big；
It is not only thin but also small that in technical performance electronic product can accomplished pressure sensitive adhesive in design, and has very in accordance with function
The reliable cementability that can be required, wherein light-cured type acrylate pressure sensitive adhesive compared with other types of pressure sensitive adhesive because having ring
Protect, water-fast heat resistance is good and is favored, but the light-cured type acrylate pressure sensitive adhesive under the prior art is when in use still
There are the following problems:
(1) can only be solidified using light, when solidification, monomer volatile quantity is big, and curing depth is inadequate, and crosslink density is too small,
Adhesive strength is not high；
(2) to the undesirable material of photopermeability (such as polycarbonate, transparent polyvinyl chloride, acrylic resin and aluminium oxide)
For, it cannot solidify the short time.
Therefore, a kind of acrylate pressure sensitive adhesive, photo-thermal dual curable glue film and preparation method thereof are developed regarding to the issue above, no
But there is urgent researching value, it may have good economic benefit and commercial application potentiality, this is exactly that the present invention is accomplished
Power where and basis.
Summary of the invention
In order to overcome the defect of the prior art as indicated above, the present inventor has made intensive studies this, is paying
After a large amount of creative works, so as to complete the present invention.
Specifically, the technical problems to be solved by the present invention are: providing a kind of acrylate pressure sensitive adhesive, photo-thermal dual curable
The adhesive glue of glue film and preparation method thereof, preparation has high-adhesion, preferably doing over again property, and it is dual solid to can be realized photo-thermal
Change, disadvantage present in existing processes is solved with this.
In order to solve the above technical problems, the technical scheme is that
A kind of acrylate pressure sensitive adhesive, by polyacrylate performed polymer with reactive diluent, photoinitiator, crosslinking agent organic
It is uniformly mixed and is made in solvent, the polyacrylate performed polymer, reactive diluent, organic solvent, photoinitiator and crosslinking agent
Weight ratio be 100:(20~50): (30~50): (0.5~3.0): (0.3~3.0).
As an improvement the polyacrylate performed polymer is to dissolve mix monomer in organic solvent, and be added
Initiator is being passed through N2Under conditions of react be made, the mix monomer includes butyl acrylate, methyl methacrylate, first
The mixture of base Glycidyl Acrylate, weight ratio are (20~30): (20~40): (40~50), the mix monomer have
Solvent and the weight ratio of initiator are 100:(30~50): (0.6~1.2).
As an improvement the reactive diluent is isobornyl acrylate or/and trimethylolpropane tris acrylic acid
Ester；The organic solvent is one of ethyl acetate, toluene or its mixed solution.
As an improvement the photoinitiator is free radical polymerization photoinitiator.
As an improvement the free radical polymerization photoinitiator is 1- hydroxy cyclohexyl phenylketone and 2- hydroxyl -2- first
Base -1- phenylacetone is compounded according to the weight ratio of 1:3~1:5.
As an improvement the crosslinking agent is isocyanates, polyisocyanates, polyamine, one in glycidol ether
Kind is a variety of.
As an improvement the initiator is dibenzoyl peroxide and azodiisobutyronitrile, the diphenyl peroxide
Formyl and azodiisobutyronitrile weight ratio are 3:1~4:1.
A kind of photo-thermal dual curable glue film, including the use of adhesive layer prepared by above-mentioned acrylate pressure sensitive adhesive, the glue
Adhensive layer is folded between the first release layer and the second release layer, and the adhesive layer is with a thickness of 2~100um, the adhesive
Layer passes through photo-thermal crosslinking Treatment.
As an improvement first release layer and the second release layer are silicone release film, first release layer
It is 1/2-1/5 with the second release layer off-type force ratio.
A kind of preparation method of photo-thermal dual curable glue film, specific steps are as follows:
The preparation of S01, polyacrylate performed polymer
S01-1, according to the weight ratio mixes butyl acrylate, methyl methacrylate, glycidyl methacrylate
Mix monomer is formed, takes 1/2 mix monomer, and the dibenzoyl peroxide for accounting for initiator total amount 1/4 is dissolved in wherein, sufficiently
Dissolution；
S01-2, equipped with blender, condenser, nitrogen tube and dropping funel four-hole boiling flask in, be added 2/3 it is organic
Solvent, and the step S01-1 solution configured is added thereto, it is passed through nitrogen, stirs and is warming up to 80~100 DEG C, stirring rate
For 120~160r/min, 1~3h of isothermal reaction；
S01-3, the dibenzoyl peroxide for dripping remaining mix monomer in 1h and accounting for initiator total amount 1/2, then
1~2h of isothermal reaction；
S01-4, then successively remaining initiator dibenzoyl peroxide and two isobutyl of initiator azo is added dropwise in supplement again
Nitrile and remaining solvent, 1~2h of isothermal reaction is cooling after making the further fully reacting of unreacted monomer, when temperature drops to
Stop reaction after 30 DEG C, obtains polyacrylate performed polymer；
The preparation of S02, acrylate pressure sensitive adhesive
Polyacrylate performed polymer, reactive diluent, organic solvent, photoinitiator and crosslinking agent are stirred according to the weight ratio
Mix uniformly mixed, obtained acrylate pressure sensitive adhesive；
The preparation of S03, photo-thermal dual curable glue film
S03-1 will be coated on after the filtering of acrylate pressure sensitive adhesive made from step S02 through knife type coater or CED coating machine
In second release level；
S03-2, by the second of coated acrylate pressure sensitive adhesive it is release be placed in UV light instrument solidify 10s~
20s carries out photo-thermal crosslinking Treatment then at 130 DEG C of 2~4min that are heating and curing, and acrylate pressure sensitive adhesive forms adhesive layer, takes out,
It encloses the first release layer and winds, photo-thermal dual curable glue film is completed in preparation.
After above-mentioned technical proposal, compared with prior art, the present invention has the following advantages:
(1) acrylate pressure sensitive adhesive selects soft monomer of the butyl acrylate (BA) as pressure sensitive adhesive system in the present invention, selects
Methyl methacrylate (MMA) is used as hard monomer, selects glycidyl methacrylate (GMA) as functional monomer, by right
The control of soft monomer, hard monomer and the ratio of functional monomer improves the adhesion strength of acrylate pressure sensitive adhesive, sufficiently meets the later period
The preparation requirement of photo-thermal dual curable glue film.
(2) initiator used in the present invention selected to be easy to get, low toxicity and lower-cost oil soluble thermal initiators: peroxide
Change dibenzoyl (BPO) and azodiisobutyronitrile (AIBN), and is reacted in the preparation process mid-early stage of polyacrylate performed polymer
Main that BPO is added, the later period adds AIBN, improves the yield of reactant；
(3) present invention in photoinitiator using free radical photo-initiation: 1- hydroxy cyclohexyl phenylketone (184) and 2-
Hydroxy-2-methyl -1- phenylacetone (1173).Wherein, 184 be white or moon white crystalline powder, maximum absorption wavelength λmaxFor
246nm, 280nm and 333nm after 184 absorb luminous energy, are cracked and are generated benzoyl radical and hydroxy-cyclohexyl free radical, and two
Kind free radical activity is very high；1173 be yellowish transparency liquid, λmaxLuminous energy is absorbed for 245nm, 280nm, 331nm, 1173
Afterwards, benzoyl radical and Alpha-hydroxy isopropyl free radical are generated through cracking, is all to cause very high 184 He of free radical of activity
Without α-H on benzoyl ortho position in 1173 molecular structure, there is an excellent thermal stability, when photodissociation does not have substituted benzyl knot
Structure, yellowing resistance are excellent；UV light can be fully absorbed using the photoinitiator compounding of 184 and 1,173 two kind of different light absorption wavelength
Energy shortens curing time；
(4) photo-thermal dual curable glue film prepared by the present invention is easy to use, when in use can as needed to clung body into
Row initial stage bonding and positioning, and can be with easy removal, doing over again property is good, can according to circumstances select suitable UV to irradiate after positioning solid
Change or be heating and curing, shortens curing time；
(5) feed way in polyacrylate pre-polymerization production procedure has important influence to the conversion ratio of system,
The present invention can be very good control reaction temperature in such a way that initiator is added in batches, decrease or even eliminate oneself in reaction
Dynamic hastening phenomenon, obtains higher conversion ratio.
To sum up, the materials in the present invention, consumption proportion and preparation process are reasonable, and the photo-thermal dual curable glue film of preparation has
High-adhesion, preferably doing over again property, and can be realized photo-thermal dual curable, curing time is shortened, production efficiency is improved.
Detailed description of the invention
Fig. 1 is a kind of structural schematic diagram of photo-thermal dual curable glue film in the present invention；
In figure: the first release layer of 1-, 2- adhesive layer, the second release layer of 3-.
Specific embodiment
It in order to make the object, technical scheme and advantages of the embodiment of the invention clearer, below will be in the embodiment of the present invention
Technical solution be clearly and completely described.The person that is not specified actual conditions in embodiment, according to normal conditions or manufacturer builds
The condition of view carries out.Reagents or instruments used without specified manufacturer is the conventional production that can be obtained by commercially available purchase
Product.
Embodiment 1:
Prepare raw material according to following weight proportion:
Mix monomer: 25 parts of butyl acrylate
30 parts of methyl methacrylate
45 parts of glycidyl methacrylate；
Initiator: oxidation dibenzoyl and totally 1 part of azodiisobutyronitrile, and oxidation dibenzoyl: azodiisobutyronitrile=
3:1；
Organic solvent: 40 parts of mixed liquor of ethyl acetate and toluene, and ethyl acetate: toluene=1:1
The preparation of S01, polyacrylate performed polymer
S01-1, according to the weight proportion of the above raw material, by butyl acrylate, methyl methacrylate, methacrylic acid ring
Oxygen propyl ester is mixed to form mix monomer, takes 1/2 mix monomer, and the dibenzoyl peroxide for accounting for initiator total amount 1/4 is molten
In wherein, sufficiently dissolve；
S01-2, equipped with blender, condenser, nitrogen tube and dropping funel four-hole boiling flask in, be added 2/3 it is organic
Solvent, and the step S01-1 solution configured is added thereto, it is passed through nitrogen, stirs and is warming up to 90 DEG C, stirring rate is
140r/min, isothermal reaction 2h；
S01-3, the dibenzoyl peroxide for dripping remaining mix monomer in 1h and accounting for initiator total amount 1/2, then
Isothermal reaction 1.5h；
S01-4, it is then supplemented that remaining initiator dibenzoyl peroxide and azodiisobutyronitrile is added dropwise, and remaining
Solvent, isothermal reaction 1.5h is cooling after making the further fully reacting of unreacted monomer, stops after temperature drops to 30 DEG C anti-
It answers, obtains polyacrylate performed polymer；
Prepare raw material according still further to following weight proportion:
Polyacrylate performed polymer: 100 parts
Reactive diluent: 35 parts of isobornyl acrylate；
Organic solvent: 40 parts of mixed liquor of ethyl acetate and toluene, and ethyl acetate: toluene=1:1
Photoinitiator: 0.5 part, by free radical polymerization photoinitiator 1- hydroxy cyclohexyl phenylketone and 2- hydroxy-2-methyl-
1- phenylacetone compounds, and 1- hydroxy cyclohexyl phenylketone: 2- hydroxy-2-methyl -1- phenylacetone=1:4
Crosslinking agent: 0.3 part of isocyanates
The preparation of S02, acrylate pressure sensitive adhesive
According to above-mentioned weight proportion by polyacrylate performed polymer, reactive diluent, organic solvent, photoinitiator and crosslinking
Agent is uniformly mixed, and acrylate pressure sensitive adhesive is made；
The preparation of S03, photo-thermal dual curable glue film
S03-1 will be coated on after the filtering of acrylate pressure sensitive adhesive made from step S02 through knife type coater or CED coating machine
On second release layer, 3 face；
Second release layer 3 of coated acrylate pressure sensitive adhesive is placed in ultraviolet light solidification instrument and solidifies 15s by S03-2, then
In 130 DEG C of 3min that are heating and curing, photo-thermal crosslinking Treatment is carried out, acrylate pressure sensitive adhesive forms adhesive layer 2,2 thickness of adhesive layer
It for 50um, takes out, encloses the first release layer 1 and wind, the first release layer and the second release layer off-type force ratio are 1/2, preparation
Complete photo-thermal dual curable glue film.
Embodiment 2:
Prepare raw material according to following weight proportion:
Mix monomer: 20 parts of butyl acrylate
40 parts of methyl methacrylate
40 parts of glycidyl methacrylate；
Initiator: oxidation dibenzoyl and totally 0.6 part of azodiisobutyronitrile, and aoxidize dibenzoyl: azodiisobutyronitrile
=3:1；
Organic solvent: 30 parts of mixed liquor of ethyl acetate and toluene, and ethyl acetate: toluene=2:1
The preparation of S01, polyacrylate performed polymer
S01-1, according to the weight proportion of the above raw material, by butyl acrylate, methyl methacrylate, methacrylic acid ring
Oxygen propyl ester is mixed to form mix monomer, takes 1/2 mix monomer, and the dibenzoyl peroxide for accounting for initiator total amount 1/4 is molten
In wherein, sufficiently dissolve；
S01-2, equipped with blender, condenser, nitrogen tube and dropping funel four-hole boiling flask in, be added 2/3 it is organic
Solvent, and the step S01-1 solution configured is added thereto, it is passed through nitrogen, stirs and is warming up to 80 DEG C, stirring rate is
120r/min, isothermal reaction 1h；
S01-3, the dibenzoyl peroxide for dripping remaining mix monomer in 1h and accounting for initiator total amount 1/2, then
Isothermal reaction 1h；
S01-4, it is then supplemented that remaining initiator dibenzoyl peroxide and azodiisobutyronitrile is added dropwise, and remaining
Solvent, isothermal reaction 2h is cooling after making the further fully reacting of unreacted monomer, stop reaction after temperature drops to 30 DEG C,
Obtain polyacrylate performed polymer；
Prepare raw material according still further to following weight proportion:
Polyacrylate performed polymer: 100 parts
Reactive diluent: 20 parts of isobornyl acrylate；
Organic solvent: 35 parts of mixed liquor of ethyl acetate and toluene, and ethyl acetate: toluene=2:1
Photoinitiator: 0.5 part, by free radical polymerization photoinitiator 1- hydroxy cyclohexyl phenylketone and 2- hydroxy-2-methyl-
1- phenylacetone compounds, and 1- hydroxy cyclohexyl phenylketone: 2- hydroxy-2-methyl -1- phenylacetone=1:4
Crosslinking agent: 1 part of isocyanates
The preparation of S02, acrylate pressure sensitive adhesive
According to above-mentioned weight proportion by polyacrylate performed polymer, reactive diluent, organic solvent, photoinitiator and crosslinking
Agent is uniformly mixed, and acrylate pressure sensitive adhesive is made；
The preparation of S03, photo-thermal dual curable glue film
S03-1 will be coated on after the filtering of acrylate pressure sensitive adhesive made from step S02 through knife type coater or CED coating machine
On second release layer, 3 face；
Second release layer 3 of coated acrylate pressure sensitive adhesive is placed in ultraviolet light solidification instrument and solidifies 10s by S03-2, then
In 130 DEG C of 2min that are heating and curing, photo-thermal crosslinking Treatment is carried out, acrylate pressure sensitive adhesive forms adhesive layer 2,2 thickness of adhesive layer
It for 2um, takes out, encloses the first release layer 1 and wind, the first release layer and the second release layer off-type force ratio are 1/3, have been prepared
At photo-thermal dual curable glue film.
Embodiment 3:
Prepare raw material according to following weight proportion:
Mix monomer: 30 parts of butyl acrylate
20 parts of methyl methacrylate
50 parts of glycidyl methacrylate；
Initiator: oxidation dibenzoyl and totally 1.2 parts of azodiisobutyronitrile, and aoxidize dibenzoyl: azodiisobutyronitrile
=4:1；
Organic solvent: 50 parts of mixed liquor of ethyl acetate and toluene, and ethyl acetate: toluene=1:2
The preparation of S01, polyacrylate performed polymer
S01-1, according to the weight proportion of the above raw material, by butyl acrylate, methyl methacrylate, methacrylic acid ring
Oxygen propyl ester is mixed to form mix monomer, takes 1/2 mix monomer, and the dibenzoyl peroxide for accounting for initiator total amount 1/4 is molten
In wherein, sufficiently dissolve；
S01-2, equipped with blender, condenser, nitrogen tube and dropping funel four-hole boiling flask in, be added 2/3 it is organic
Solvent, and the step S01-1 solution configured is added thereto, it is passed through nitrogen, stirs and is warming up to 100 DEG C, stirring rate is
160r/min, isothermal reaction 3h；
S01-3, the dibenzoyl peroxide for dripping remaining mix monomer in 1h and accounting for initiator total amount 1/2, then
Isothermal reaction 2h；
S01-4, it is then supplemented that remaining initiator dibenzoyl peroxide and azodiisobutyronitrile is added dropwise, and remaining
Solvent, isothermal reaction 1h is cooling after making the further fully reacting of unreacted monomer, stop reaction after temperature drops to 30 DEG C,
Obtain polyacrylate performed polymer；
Prepare raw material according still further to following weight proportion:
Polyacrylate performed polymer: 100 parts
Reactive diluent: 25 parts of isobornyl acrylate；
Organic solvent: 30 parts of mixed liquor of ethyl acetate and toluene, and ethyl acetate: toluene=1:2
Photoinitiator: 1.5 parts, by free radical polymerization photoinitiator 1- hydroxy cyclohexyl phenylketone and 2- hydroxy-2-methyl-
1- phenylacetone compounds, and 1- hydroxy cyclohexyl phenylketone: 2- hydroxy-2-methyl -1- phenylacetone=1:4
Crosslinking agent: 0.3 part of isocyanates
The preparation of S02, acrylate pressure sensitive adhesive
According to above-mentioned weight proportion by polyacrylate performed polymer, reactive diluent, organic solvent, photoinitiator and crosslinking
Agent is uniformly mixed, and acrylate pressure sensitive adhesive is made；
The preparation of S03, photo-thermal dual curable glue film
S03-1 will be coated on after the filtering of acrylate pressure sensitive adhesive made from step S02 through knife type coater or CED coating machine
On second release layer, 3 face；
Second release layer 3 of coated acrylate pressure sensitive adhesive is placed in ultraviolet light solidification instrument and solidifies 20s by S03-2, then
In 130 DEG C of 4min that are heating and curing, photo-thermal crosslinking Treatment is carried out, acrylate pressure sensitive adhesive forms adhesive layer 2,2 thickness of adhesive layer
It for 100um, takes out, encloses the first release layer 1 and wind, the first release layer and the second release layer off-type force ratio are 1/4, preparation
Complete photo-thermal dual curable glue film.
Embodiment 4:
Prepare raw material according to following weight proportion:
Mix monomer: 30 parts of butyl acrylate
40 parts of methyl methacrylate
30 parts of glycidyl methacrylate；
Initiator: oxidation dibenzoyl and totally 0.8 part of azodiisobutyronitrile, and aoxidize dibenzoyl: azodiisobutyronitrile
=3.5:1；
Organic solvent: 45 parts of ethyl acetate, the preparation of S01, polyacrylate performed polymer
S01-1, according to the weight proportion of the above raw material, by butyl acrylate, methyl methacrylate, methacrylic acid ring
Oxygen propyl ester is mixed to form mix monomer, takes 1/2 mix monomer, and the dibenzoyl peroxide for accounting for initiator total amount 1/4 is molten
In wherein, sufficiently dissolve；
S01-2, equipped with blender, condenser, nitrogen tube and dropping funel four-hole boiling flask in, be added 2/3 it is organic
Solvent, and the step S01-1 solution configured is added thereto, it is passed through nitrogen, stirs and is warming up to 85 DEG C, stirring rate is
130r/min, isothermal reaction 1.5h；
S01-3, the dibenzoyl peroxide for dripping remaining mix monomer in 1h and accounting for initiator total amount 1/2, then
Isothermal reaction 1.3h；
S01-4, it is then supplemented that remaining initiator dibenzoyl peroxide and azodiisobutyronitrile is added dropwise, and remaining
Solvent, isothermal reaction 1.3h is cooling after making the further fully reacting of unreacted monomer, stops after temperature drops to 30 DEG C anti-
It answers, obtains polyacrylate performed polymer；
Prepare raw material according still further to following weight proportion:
Polyacrylate performed polymer: 100 parts
Reactive diluent: 50 parts of trimethylolpropane trimethacrylate；
Organic solvent: 50 parts of photoinitiators of ethyl acetate: 1.5 parts, by free radical polymerization photoinitiator 1- hydroxy-cyclohexyl
Benzophenone and 2- hydroxy-2-methyl -1- phenylacetone compound, and 1- hydroxy cyclohexyl phenylketone: 2- hydroxy-2-methyl -
1- phenylacetone=1:4
Crosslinking agent: 1 part of isocyanates
The preparation of S02, acrylate pressure sensitive adhesive
According to above-mentioned weight proportion by polyacrylate performed polymer, reactive diluent, organic solvent, photoinitiator and crosslinking
Agent is uniformly mixed, and acrylate pressure sensitive adhesive is made；
The preparation of S03, photo-thermal dual curable glue film
S03-1 will be coated on after the filtering of acrylate pressure sensitive adhesive made from step S02 through knife type coater or CED coating machine
On second release layer, 3 face；
Second release layer 3 of coated acrylate pressure sensitive adhesive is placed in ultraviolet light solidification instrument and solidifies 13s by S03-2, then
In 130 DEG C of 2.5min that are heating and curing, photo-thermal crosslinking Treatment is carried out, acrylate pressure sensitive adhesive forms adhesive layer 2, and adhesive layer 2 is thick
Degree is 25um, takes out, encloses the first release layer 1 and wind, and the first release layer and the second release layer off-type force ratio are 1/4, system
It is standby to complete photo-thermal dual curable glue film.
Embodiment 5:
Prepare raw material according to following weight proportion:
Mix monomer: 25 parts of butyl acrylate
35 parts of methyl methacrylate
40 parts of glycidyl methacrylate；
Initiator: oxidation dibenzoyl and totally 2 parts of azodiisobutyronitrile, and oxidation dibenzoyl: azodiisobutyronitrile=
3.3:1；
Organic solvent: 35 parts of toluene；
The preparation of S01, polyacrylate performed polymer
S01-1, according to the weight proportion of the above raw material, by butyl acrylate, methyl methacrylate, methacrylic acid ring
Oxygen propyl ester is mixed to form mix monomer, takes 1/2 mix monomer, and the dibenzoyl peroxide for accounting for initiator total amount 1/4 is molten
In wherein, sufficiently dissolve；
S01-2, equipped with blender, condenser, nitrogen tube and dropping funel four-hole boiling flask in, be added 2/3 it is organic
Solvent, and the step S01-1 solution configured is added thereto, it is passed through nitrogen, stirs and is warming up to 95 DEG C, stirring rate is
150r/min, isothermal reaction 2.5h；
S01-3, the dibenzoyl peroxide for dripping remaining mix monomer in 1h and accounting for initiator total amount 1/2, then
Isothermal reaction 1.8h；
S01-4, it is then supplemented that remaining initiator dibenzoyl peroxide and azodiisobutyronitrile is added dropwise, and remaining
Solvent, isothermal reaction 1.8h is cooling after making the further fully reacting of unreacted monomer, stops after temperature drops to 30 DEG C anti-
It answers, obtains polyacrylate performed polymer；
Prepare raw material according still further to following weight proportion:
Polyacrylate performed polymer: 100 parts
Reactive diluent: 25 parts of trimethylolpropane trimethacrylate；
Organic solvent: 30 parts of toluene；
Photoinitiator: 3 parts, by free radical polymerization photoinitiator 1- hydroxy cyclohexyl phenylketone and 2- hydroxy-2-methyl -1-
Phenylacetone compounds, and 1- hydroxy cyclohexyl phenylketone: 2- hydroxy-2-methyl -1- phenylacetone=1:4
Crosslinking agent: 0.3 part of isocyanates
The preparation of S02, acrylate pressure sensitive adhesive
According to above-mentioned weight proportion by polyacrylate performed polymer, reactive diluent, organic solvent, photoinitiator and crosslinking
Agent is uniformly mixed, and acrylate pressure sensitive adhesive is made；
The preparation of S03, photo-thermal dual curable glue film
S03-1 will be coated on after the filtering of acrylate pressure sensitive adhesive made from step S02 through knife type coater or CED coating machine
On second release layer, 3 face；
Second release layer 3 of coated acrylate pressure sensitive adhesive is placed in ultraviolet light solidification instrument and solidifies 18s by S03-2, then
In 130 DEG C of 3.5min that are heating and curing, photo-thermal crosslinking Treatment is carried out, acrylate pressure sensitive adhesive forms adhesive layer 2, and adhesive layer 2 is thick
Degree is 85um, takes out, encloses the first release layer 1 and wind, and the first release layer and the second release layer off-type force ratio are 1/5, system
It is standby to complete photo-thermal dual curable glue film.
Embodiment 6:
Prepare raw material according to following weight proportion:
Mix monomer: 20 parts of butyl acrylate
35 parts of methyl methacrylate
45 parts of glycidyl methacrylate；
Initiator: oxidation dibenzoyl and totally 2.5 parts of azodiisobutyronitrile, and aoxidize dibenzoyl: azodiisobutyronitrile
=4:1；
Organic solvent: 30 parts of ethyl acetate
The preparation of S01, polyacrylate performed polymer
S01-1, according to the weight proportion of the above raw material, by butyl acrylate, methyl methacrylate, methacrylic acid ring
Oxygen propyl ester is mixed to form mix monomer, takes 1/2 mix monomer, and the dibenzoyl peroxide for accounting for initiator total amount 1/4 is molten
In wherein, sufficiently dissolve；
S01-2, equipped with blender, condenser, nitrogen tube and dropping funel four-hole boiling flask in, be added 2/3 it is organic
Solvent, and the step S01-1 solution configured is added thereto, it is passed through nitrogen, stirs and is warming up to 100 DEG C, stirring rate is
156r/min, isothermal reaction 2.8h；
S01-3, the dibenzoyl peroxide for dripping remaining mix monomer in 1h and accounting for initiator total amount 1/2, then
Isothermal reaction 2h；
S01-4, it is then supplemented that remaining initiator dibenzoyl peroxide and azodiisobutyronitrile is added dropwise, and remaining
Solvent, isothermal reaction 1h is cooling after making the further fully reacting of unreacted monomer, stop reaction after temperature drops to 30 DEG C,
Obtain polyacrylate performed polymer；
Prepare raw material according still further to following weight proportion:
Polyacrylate performed polymer: 100 parts
Reactive diluent: 45 parts of trimethylolpropane trimethacrylate；
Organic solvent: 30 parts of ethyl acetate
Photoinitiator: 3.0 parts, by free radical polymerization photoinitiator 1- hydroxy cyclohexyl phenylketone and 2- hydroxy-2-methyl-
1- phenylacetone compounds, and 1- hydroxy cyclohexyl phenylketone: 2- hydroxy-2-methyl -1- phenylacetone=1:4
Crosslinking agent: 3.0 parts of isocyanates
The preparation of S02, acrylate pressure sensitive adhesive
According to above-mentioned weight proportion by polyacrylate performed polymer, reactive diluent, organic solvent, photoinitiator and crosslinking
Agent is uniformly mixed, and acrylate pressure sensitive adhesive is made；
The preparation of S03, photo-thermal dual curable glue film
S03-1 will be coated on after the filtering of acrylate pressure sensitive adhesive made from step S02 through knife type coater or CED coating machine
On second release layer, 3 face；
Second release layer 3 of coated acrylate pressure sensitive adhesive is placed in ultraviolet light solidification instrument and solidifies 20s by S03-2, then
In 130 DEG C of 4min that are heating and curing, photo-thermal crosslinking Treatment is carried out, acrylate pressure sensitive adhesive forms adhesive layer 2,2 thickness of adhesive layer
It for 90um, takes out, encloses the first release layer 1 and wind, the first release layer and the second release layer off-type force ratio are 1/5, preparation
Complete photo-thermal dual curable glue film.
It is viscous to steel plate (BASUS) that photo-thermal dual curable glue film obtained by above-described embodiment 1-6 is tested into the different UV times respectively
Put forth effort, adhesion force test method is JIS Z 0237, and test result is as shown in table 1:
Table 1: photo-thermal dual curable glue film performance test result obtained by embodiment 1-6
It should be appreciated that the purposes of these embodiments is merely to illustrate the present invention and is not intended to limit protection model of the invention
It encloses.In addition, it should also be understood that, after reading the technical contents of the present invention, those skilled in the art can make the present invention each
Kind change, modification and/or variation, all these equivalent forms equally fall within guarantor defined by the application the appended claims
Within the scope of shield.
Claims (10)
1. a kind of acrylate pressure sensitive adhesive, which is characterized in that by polyacrylate performed polymer and reactive diluent, photoinitiator, friendship
Join agent and be uniformly mixed in organic solvent and is made, it is the polyacrylate performed polymer, reactive diluent, organic solvent, light-initiated
The weight ratio of agent and crosslinking agent is 100:(20~50): (30~50): (0.5~3.0): (0.3~3.0).
2. a kind of acrylate pressure sensitive adhesive as described in claim 1, which is characterized in that the polyacrylate performed polymer is will to mix
It closes monomer dissolution in organic solvent, and initiator is added, be passed through N2Under conditions of react be made, the mix monomer includes
Butyl acrylate, methyl methacrylate, glycidyl methacrylate mixture, weight ratio be (20~30): (20~
40): (40~50), the weight ratio of the mix monomer, organic solvent and initiator are 100:(30~50): (0.6~1.2).
3. a kind of acrylate pressure sensitive adhesive as claimed in claim 2, which is characterized in that the reactive diluent is the different ice of acrylic acid
Piece ester or/and trimethylolpropane trimethacrylate；The organic solvent is that one of ethyl acetate, toluene or its mixing are molten
Liquid.
4. a kind of acrylate pressure sensitive adhesive as claimed in claim 3, which is characterized in that the photoinitiator is radical polymerization light combination
Initiator.
5. a kind of acrylate pressure sensitive adhesive as claimed in claim 4, which is characterized in that the free radical polymerization photoinitiator is 1-
Hydroxy cyclohexyl phenylketone and 2- hydroxy-2-methyl -1- phenylacetone are compounded according to the weight ratio of 1:3~1:5.
6. a kind of acrylate pressure sensitive adhesive as claimed in claim 5, which is characterized in that the crosslinking agent is isocyanates, polyisocyanate
One of cyanate, polyamine, glycidol ether are a variety of.
7. a kind of acrylate pressure sensitive adhesive as claimed in claim 6, which is characterized in that the initiator is dibenzoyl peroxide
And azodiisobutyronitrile, the dibenzoyl peroxide and azodiisobutyronitrile weight ratio are 3:1~4:1.
8. a kind of photo-thermal dual curable glue film, which is characterized in that prepared including the use of acrylate pressure sensitive adhesive as claimed in claim 7
Adhesive layer, the adhesive layer is folded between the first release layer and the second release layer, the adhesive layer with a thickness of 2~
100um, the adhesive layer pass through photo-thermal crosslinking Treatment.
9. a kind of photo-thermal dual curable glue film as claimed in claim 7, which is characterized in that first release layer and second from
Type layer is silicone release film, and first release layer and the second release layer off-type force ratio are 1/2-1/5.
10. the method for preparing photo-thermal dual curable glue film as claimed in claim 7, which is characterized in that the specific steps of preparation
Are as follows:
The preparation of S01, polyacrylate performed polymer
S01-1, according to the weight ratio, butyl acrylate, methyl methacrylate, glycidyl methacrylate are mixed to form
Mix monomer takes 1/2 mix monomer, and the dibenzoyl peroxide for accounting for initiator total amount 1/4 is dissolved in wherein, sufficiently molten
Solution；
S01-2, equipped with blender, condenser, nitrogen tube and dropping funel four-hole boiling flask in, 2/3 organic solvent is added,
And be added thereto the step S01-1 solution configured, it is passed through nitrogen, stirs and is warming up to 80~100 DEG C, stirring rate 120
~160r/min, 1~3h of isothermal reaction；
S01-3, the dibenzoyl peroxide for dripping remaining mix monomer in 1h and accounting for initiator total amount 1/2, then constant temperature
React 1~2h；
S01-4, then successively remaining initiator dibenzoyl peroxide and initiator azodiisobutyronitrile is added dropwise in supplement again, with
And remaining solvent, 1~2h of isothermal reaction, it is cooling after making the further fully reacting of unreacted monomer, after temperature drops to 30 DEG C
Stop reaction, obtains polyacrylate performed polymer；
The preparation of S02, acrylate pressure sensitive adhesive
Polyacrylate performed polymer, reactive diluent, organic solvent, photoinitiator and crosslinking agent are stirred according to the weight ratio mixed
It closes uniformly, acrylate pressure sensitive adhesive is made；
The preparation of S03, photo-thermal dual curable glue film
S03-1 will be coated on second through knife type coater or CED coating machine after the filtering of acrylate pressure sensitive adhesive made from step S02
In release level；
The second of coated acrylate pressure sensitive adhesive release be placed in UV light instrument is solidified 10s~20s by S03-2, then
In 130 DEG C of 2~4min that are heating and curing, photo-thermal crosslinking Treatment is carried out, acrylate pressure sensitive adhesive forms adhesive layer, takes out, and encloses the
One release layer is simultaneously wound, and photo-thermal dual curable glue film is completed in preparation.
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| CN113969111A (en) * | 2021-12-01 | 2022-01-25 | 湖北航天化学技术研究所 | Secondary curing UV pressure-sensitive adhesive and preparation method of secondary curing UV pressure-sensitive adhesive and explosion-proof membrane |
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| CN110423569A (en) * | 2019-08-14 | 2019-11-08 | 惠州合益创光学材料有限公司 | Rupture pressure disc and its preparation method and application in a kind of screen |
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| CN111846874B (en) * | 2020-07-17 | 2022-04-05 | 东莞华誉精密技术有限公司 | Automatic overturning and laminating process for front shell of mobile phone |
| CN112743947A (en) * | 2020-12-29 | 2021-05-04 | 潍坊同有新材料科技有限公司 | Photo-thermal dual-curing diaphragm composite material and preparation method thereof |
| CN112743947B (en) * | 2020-12-29 | 2022-08-16 | 潍坊同有新材料科技有限公司 | Photo-thermal dual-curing diaphragm composite material and preparation method thereof |
| CN113969111A (en) * | 2021-12-01 | 2022-01-25 | 湖北航天化学技术研究所 | Secondary curing UV pressure-sensitive adhesive and preparation method of secondary curing UV pressure-sensitive adhesive and explosion-proof membrane |
| WO2023098104A1 (en) * | 2021-12-01 | 2023-06-08 | 湖北航天化学技术研究所 | Secondary cured uv pressure-sensitive adhesive, and preparation methods for same and explosion-proof film |
| CN114381208A (en) * | 2022-01-13 | 2022-04-22 | 广州惠利电子材料有限公司 | Photo-thermal dual-curing adhesive |
| CN116525871A (en) * | 2023-06-29 | 2023-08-01 | 山东同有新材料科技有限公司 | Acrylic ester type hot-melt frame film and manufacturing method thereof |
| CN116525871B (en) * | 2023-06-29 | 2023-09-15 | 山东同有新材料科技有限公司 | Acrylic ester type hot-melt frame film and manufacturing method thereof |
| WO2024169178A1 (en) * | 2023-09-21 | 2024-08-22 | 南京斯瑞奇医疗用品有限公司 | Low-sensitization pressure-sensitive adhesive for medical dressing and preparation method therefor |
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