CN110563864A - Acrylate monomer, synthesis method thereof and UV (ultraviolet) moisture dual-curing hot melt adhesive film - Google Patents
Acrylate monomer, synthesis method thereof and UV (ultraviolet) moisture dual-curing hot melt adhesive film Download PDFInfo
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- CN110563864A CN110563864A CN201910802960.2A CN201910802960A CN110563864A CN 110563864 A CN110563864 A CN 110563864A CN 201910802960 A CN201910802960 A CN 201910802960A CN 110563864 A CN110563864 A CN 110563864A
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- acrylate monomer
- adhesive film
- hot melt
- melt adhesive
- containing acrylate
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 61
- 239000000178 monomer Substances 0.000 title claims abstract description 59
- 239000004831 Hot glue Substances 0.000 title claims abstract description 31
- 238000001308 synthesis method Methods 0.000 title abstract description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 49
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 49
- 239000010703 silicon Substances 0.000 claims abstract description 49
- 238000006243 chemical reaction Methods 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 17
- -1 sodium alkoxide Chemical class 0.000 claims abstract description 14
- 239000011734 sodium Substances 0.000 claims abstract description 11
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 11
- 239000003960 organic solvent Substances 0.000 claims abstract description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 42
- 238000001723 curing Methods 0.000 claims description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 15
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 14
- 238000001035 drying Methods 0.000 claims description 14
- 238000005406 washing Methods 0.000 claims description 14
- 238000001914 filtration Methods 0.000 claims description 13
- 238000010438 heat treatment Methods 0.000 claims description 8
- PUGOMSLRUSTQGV-UHFFFAOYSA-N 2,3-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OCC(OC(=O)C=C)COC(=O)C=C PUGOMSLRUSTQGV-UHFFFAOYSA-N 0.000 claims description 7
- 239000002994 raw material Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 4
- 230000002194 synthesizing effect Effects 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 3
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims 4
- 238000003786 synthesis reaction Methods 0.000 claims 4
- 238000006845 Michael addition reaction Methods 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 4
- 239000012535 impurity Substances 0.000 abstract description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
- 230000007935 neutral effect Effects 0.000 description 11
- 238000000746 purification Methods 0.000 description 11
- 238000002390 rotary evaporation Methods 0.000 description 11
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 238000010030 laminating Methods 0.000 description 9
- 239000002313 adhesive film Substances 0.000 description 8
- 238000004806 packaging method and process Methods 0.000 description 7
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 7
- 230000032683 aging Effects 0.000 description 5
- 238000013008 moisture curing Methods 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 238000012512 characterization method Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000005464 sample preparation method Methods 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 238000003848 UV Light-Curing Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000012943 hotmelt Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 238000004383 yellowing Methods 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 238000003475 lamination Methods 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035939 shock Effects 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical group CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000032798 delamination Effects 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000000156 glass melt Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000009863 impact test Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- 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
- C08F30/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F30/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F30/08—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
-
- 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
Landscapes
- 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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention belongs to the technical field of preparation of acrylate monomers, and particularly relates to an acrylate monomer and a synthesis method thereof, and a UV (ultraviolet) moisture dual-curing hot melt adhesive film. The hyperbranched silicon-containing acrylate monomer is prepared by KH550, triacrylate and sodium alkoxide in an organic solvent by using amino double bond Michael addition reaction in one step, can stably control the reaction temperature and speed, has the advantages of simple reaction, controllable process, high product purity and the like, is very suitable for preparing a UV (ultraviolet) moisture dual-curing hot melt adhesive film, can reduce impurities in the UV moisture dual-curing hot melt adhesive film, and improves the performance of the hot melt adhesive film.
Description
Technical Field
The invention belongs to the technical field of preparation of acrylate monomers, and particularly relates to an acrylate monomer and a synthesis method thereof, and a UV (ultraviolet) moisture dual-curing hot melt adhesive film.
Background
the hot-melt optical adhesive film is popular in recent years, is suitable for the lamination of screens with various sizes, and is simple in processing process and easy to disassemble reversely. The hot-melt optical adhesive film can reduce the bonding threshold of the touch screen and the liquid crystal module thereof and improve the bonding yield.
the traditional optical packaging is generally synthesized by conventional acrylate monomers (such as methyl acrylate, ethyl acrylate, 2-methyl methacrylate, 2-ethyl methacrylate and the like) and other auxiliary materials (such as a photoinitiator, a coupling agent, a catalyst, an antioxidant, a light stabilizer and the like), and the curing of shadow parts shielded at the corners of a screen with an overlarge size is incomplete, so that the UV irradiation intensity of a touch screen frame or a place with colored ink at the edge is weak, the peeling strength in the field of black edges is insufficient, delamination can be generated after long-term use, the defect rate is high, the rework is complex, and the traditional optical packaging is difficult to be suitable for the automatic packaging of an overlarge display screen with 60-90 inches.
disclosure of Invention
The invention aims to provide an acrylate monomer, a synthesis method thereof and a UV (ultraviolet) and moisture dual-curing hot melt adhesive film.
In order to solve the technical problems, the invention provides a hyperbranched silicon-containing acrylate monomer, which has a structural formula as follows:
wherein
R1Is CH2-CH2-Si(OMe)3。
Further, R2Is H or CH3。
In a second aspect, the invention also provides a method for synthesizing a hyperbranched silicon-containing acrylate monomer, comprising: mixing KH550, triacrylate and sodium alkoxide in an organic solvent; heating for reaction; filtering and washing; and drying and purifying to obtain the hyperbranched silicon-containing acrylate monomer.
Further, the reaction formula of the heating reaction is as follows:
further, the molar ratio of the KH550 to the triacrylate to the sodium alkoxide is 1: 1-3: 0.005-0.01.
Further, the organic solvent includes: one or more of THF, dichloromethane, dioxane and ethyl formate.
Further, the triacrylate comprises any one of glycerol triacrylate, trimethylolpropane triacrylate, or a mixture of both.
In a third aspect, the invention further provides a UV moisture dual-curing hot melt adhesive film, which is suitable for being prepared by using the hyperbranched silicon-containing acrylate monomer as a main raw material.
The hyperbranched silicon-containing acrylate monomer and the synthesis method thereof have the beneficial effects that the hyperbranched silicon-containing acrylate monomer is synthesized by the UV moisture dual-curing hot melt adhesive film in an organic solvent through KH550, triacrylate and sodium alkoxide, and the hyperbranched silicon-containing acrylate monomer is prepared by one-step amino double bond Michael addition reaction, so that the reaction temperature and the reaction speed can be stably controlled, the method has the advantages of simple reaction, controllable process, high product purity and the like, is very suitable for preparing the UV moisture dual-curing hot melt adhesive film, can reduce impurities in the UV moisture dual-curing hot melt adhesive film, and improves the performance of the hot melt adhesive film so as to be suitable for UV and moisture dual curing.
Additional features and advantages of the invention will be set forth in the description which follows, and in part will be obvious from the description, or may be learned by practice of the invention. The objectives and other advantages of the invention will be realized and attained by the structure particularly pointed out in the written description and claims hereof as well as the appended drawings.
In order to make the aforementioned and other objects, features and advantages of the present invention comprehensible, preferred embodiments accompanied with figures are described in detail below.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, and it is obvious that the drawings in the following description are some embodiments of the present invention, and other drawings can be obtained by those skilled in the art without creative efforts.
FIG. 1 is a flow chart of a process for preparing a hyperbranched silicon-containing acrylate monomer of the invention;
FIG. 2 is an infrared spectrum of a hyperbranched silicon-containing acrylate monomer of the invention;
FIG. 3 shows the CDCl of the hyperbranched silicon-containing acrylate monomer of the invention3Hydrogen spectra in solution;
FIG. 4 is a GPC chart of a hyperbranched silicon-containing acrylate monomer of the invention in THF solution.
Detailed Description
To make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions of the present invention will be clearly and completely described below with reference to the accompanying drawings, and it is apparent that the described embodiments are some, but not all embodiments of the present invention. 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.
Interpretation of custom nouns or English abbreviations:
UV: ultraviolet rays;
KH 550: KH550 type silane coupling agent with CAS number 919-30-2;
THF: tetrahydrofuran, a heterocyclic organic compound;
EVA resin: from nonpolar, crystalline vinyl monomers (C)2H4) And a strongly polar, noncrystalline vinyl acetate monomer (CH)3COOC2H3) A thermoplastic resin obtained by high-pressure bulk polymerization in the presence of an initiator;
POE resin: a polymer blend comprised of octene and a polyolefin resin, the continuous phase and the dispersed phase exhibiting two phase separation;
Triacrylate: acrylates containing three functional groups, such as glycerol triacrylate, trimethylolpropane triacrylate (TMPTA), or mixtures of the two;
trimethylolpropane triacrylate: i.e., TMPTA, having the formula (CH)2=CHCOOCH2)3-CCH2CH3。
Example 1
this example 1 provides a hyperbranched silicon-containing acrylate monomer, whose structural formula is:
wherein R is1Is CH2-CH2-Si(OMe)3;R2is H or CH3。
Example 2
FIG. 1 is a flow chart of the preparation process of the hyperbranched silicon-containing acrylate monomer of the invention.
As shown in fig. 1, based on example 1, this example 2 provides a method for synthesizing a hyperbranched silicon-containing acrylate monomer, including: mixing KH550, triacrylate and sodium alkoxide in an organic solvent; heating for reaction; filtering and washing; and drying and purifying to obtain the hyperbranched silicon-containing acrylate monomer. Specifically, the reaction product can be washed by adding a proper amount of dichloromethane, the pH value of the washing value is neutral, then anhydrous magnesium sulfate is added for drying, and the hyperbranched silicon-containing acrylate monomer is obtained through rotary evaporation and purification.
For the content of the components of the hyperbranched silicon-containing acrylate monomer and the specific implementation process, reference is made to the relevant discussion in example 1, which is not repeated here.
Wherein the reaction formula of the heating reaction (i.e. the amino double bond Michael addition reaction) is as follows:
Controlling the molar ratio of KH550, triacrylate and sodium alkoxide to be 1: 1-3: 0.005-0.01, and the reaction can be completed by keeping the heating temperature at about 50 ℃ and the reaction time at about 48 hours.
Alternatively, the molar ratio of the KH550 to the triacrylate to the sodium alkoxide can also be 1: 2: 0.007-0.008. Optionally, the organic solvent includes but is not limited to one or more of THF, dichloromethane, dioxane, ethyl formate; the organic solvent can make the heating temperature of the reactants more uniform and more stable, and is convenient to control the reaction rate.
Optionally, the triacrylate includes, but is not limited to, any one of glycerol triacrylate, trimethylolpropane triacrylate, or a mixture of both.
alternatively, the sodium alkoxide includes, but is not limited to, sodium methoxide, sodium ethoxide, and the like.
Example 3
based on example 1 or 2, this example 3 provides a UV moisture dual-curing hot melt adhesive film, which is suitable for being prepared by using the hyperbranched silicon-containing acrylate monomer as the main raw material.
of course, the hot melt adhesive film also needs to be added with other raw materials such as resin, photoinitiator, coupling agent, catalyst, antioxidant and light stabilizer during the preparation process, and all the materials are conventional materials and are not listed in detail here.
Specifically, the hot melt adhesive film can be used as a hot melt optical adhesive film, can be cured in the environment of UV light and/or moisture, is used for packaging an oversized touch screen, and effectively solves the problem that the black edge field cannot be completely cured.
For the content of the components of the hyperbranched silicon-containing acrylate monomer and the specific implementation process, reference is made to the relevant discussion in example 1 or 2, which is not described in detail herein.
In summary, the hyperbranched silicon-containing acrylate monomer, the synthesis method thereof, and the hot melt adhesive film in embodiments 1 to 3 are prepared by synthesizing the hyperbranched silicon-containing acrylate monomer in an organic solvent through KH550, triacrylate, and sodium alkoxide, and performing michael addition reaction on amino double bonds, so that the reaction temperature and speed can be stably controlled, and the hyperbranched silicon-containing acrylate monomer has the advantages of simple reaction, controllable process, high product purity, and the like, is very suitable for preparing a UV moisture dual-cured hot melt adhesive film, can reduce impurities in the UV moisture dual-cured hot melt adhesive film, and improves the performance of the hot melt adhesive film.
Example 4
1 part by mol of KH550 and 1 part by mol of trimethylolpropane triacrylate, and 0.01 part by mol of sodium ethoxide were added and mixed in a solvent solution at room temperature. Then the temperature was raised to 50 ℃ to react for 48 hours. And after the reaction is finished, filtering, adding a proper amount of dichloromethane for washing, adding anhydrous magnesium sulfate for drying under the condition that the pH value of the solution is neutral, and performing rotary evaporation and purification to obtain the hyperbranched silicon-containing acrylate monomer.
Example 5
1 part by mol of KH550 and 1 part by mol of trimethylolpropane triacrylate, and 0.005 part by mol of sodium ethoxide were added and mixed in a solvent solution at room temperature. Then the temperature was raised to 50 ℃ to react for 48 hours. And after the reaction is finished, filtering, adding a proper amount of dichloromethane for washing, adding anhydrous magnesium sulfate for drying under the condition that the pH value of the solution is neutral, and performing rotary evaporation and purification to obtain the hyperbranched silicon-containing acrylate monomer.
Example 6
1 part by mol of KH550 and 2 parts by mol of trimethylolpropane triacrylate, and 0.01 part by mol of sodium ethoxide were added and mixed in a solvent solution at room temperature. Then the temperature was raised to 50 ℃ to react for 48 hours. And after the reaction is finished, filtering, adding a proper amount of dichloromethane for washing, adding anhydrous magnesium sulfate for drying under the condition that the pH value of the solution is neutral, and performing rotary evaporation and purification to obtain the hyperbranched silicon-containing acrylate monomer.
Example 7
1 part by mol of KH550 and 2 parts by mol of trimethylolpropane triacrylate, and 0.009 parts by mol of sodium ethoxide were added and mixed in a solvent solution at room temperature. Then the temperature was raised to 50 ℃ to react for 48 hours. And after the reaction is finished, filtering, adding a proper amount of dichloromethane for washing, adding anhydrous magnesium sulfate for drying under the condition that the pH value of the solution is neutral, and performing rotary evaporation and purification to obtain the hyperbranched silicon-containing acrylate monomer.
Example 8
1 part by mol of KH550 and 3 parts by mol of trimethylolpropane triacrylate, and 0.01 part by mol of sodium ethoxide were added and mixed in a solvent solution at room temperature. Then the temperature was raised to 50 ℃ to react for 48 hours. And after the reaction is finished, filtering, adding a proper amount of dichloromethane for washing, adding anhydrous magnesium sulfate for drying under the condition that the pH value of the solution is neutral, and performing rotary evaporation and purification to obtain the hyperbranched silicon-containing acrylate monomer.
example 9
1 part by mol of KH550 and 3 parts by mol of trimethylolpropane triacrylate, and 0.0075 parts by mol of sodium ethoxide were added and mixed in a solvent solution at room temperature. Then the temperature was raised to 50 ℃ to react for 48 hours. And after the reaction is finished, filtering, adding a proper amount of dichloromethane for washing, adding anhydrous magnesium sulfate for drying under the condition that the pH value of the solution is neutral, and performing rotary evaporation and purification to obtain the hyperbranched silicon-containing acrylate monomer.
Example 10
1 part by mole of KH550 and 3 parts by mole of trimethylolpropane triacrylate, and 0.005 part by mole of sodium methoxide were added and mixed in a solvent solution at room temperature. Then the temperature was raised to 50 ℃ to react for 48 hours. And after the reaction is finished, filtering, adding a proper amount of dichloromethane for washing, adding anhydrous magnesium sulfate for drying under the condition that the pH value of the solution is neutral, and performing rotary evaporation and purification to obtain the hyperbranched silicon-containing acrylate monomer.
Example 11
1 part by mol of KH550 and 3 parts by mol of glycerol triacrylate, and 0.007 part by mol of sodium methoxide were added and mixed in a solvent solution at room temperature. Then the temperature was raised to 50 ℃ to react for 48 hours. And after the reaction is finished, filtering, adding a proper amount of dichloromethane for washing, adding anhydrous magnesium sulfate for drying under the condition that the pH value of the solution is neutral, and performing rotary evaporation and purification to obtain the hyperbranched silicon-containing acrylate monomer.
Example 12
1 part by mole of KH550 and 2.5 parts by mole of glycerol triacrylate, and 0.006 part by mole of sodium methoxide were added and mixed in a solvent solution at room temperature. Then the temperature was raised to 50 ℃ to react for 48 hours. And after the reaction is finished, filtering, adding a proper amount of dichloromethane for washing, adding anhydrous magnesium sulfate for drying under the condition that the pH value of the solution is neutral, and performing rotary evaporation and purification to obtain the hyperbranched silicon-containing acrylate monomer.
Example 13
1 part by mole of KH550 and 1.5 parts by mole of glycerol triacrylate, and 0.008 part by mole of sodium methoxide were added and mixed in a solvent solution at room temperature. Then the temperature was raised to 50 ℃ to react for 48 hours. And after the reaction is finished, filtering, adding a proper amount of dichloromethane for washing, adding anhydrous magnesium sulfate for drying under the condition that the pH value of the solution is neutral, and performing rotary evaporation and purification to obtain the hyperbranched silicon-containing acrylate monomer.
Example 14
FIG. 2 is an infrared spectrum of a hyperbranched silicon-containing acrylate monomer of the invention.
FIG. 3 shows the CDCl of the hyperbranched silicon-containing acrylate monomer of the invention3Hydrogen spectrum in solution.
FIG. 4 is a GPC chart of a hyperbranched silicon-containing acrylate monomer of the invention in THF solution.
As shown in fig. 2 to 4, in this example 14, the hyperbranched silicon-containing acrylate monomer obtained in example 4 is characterized by an infrared spectrum (fig. 2), a hydrogen spectrum (fig. 3) and a GPC spectrum (fig. 4).
(1) Referring to FIG. 2, it can be seen from the infrared spectrum that 1270cm on the abscissa-1and 985cm-1Respectively, the stretching vibration peaks of amido bond and acrylic ester C-O, and 1730cm-1、1630cm-1、1180cm-1And 800cm-1Are characteristic absorption peaks for acrylate functionality. Wherein the depth is 1080cm-1Is the result of the overlap of characteristic peaks of the Si-O-C and ester functional groups.
(2) Referring to fig. 3, it can be found by hydrogen spectroscopy that three sets of characteristic absorption peaks with the abscissa of 5.80-6.56ppm verify the acrylate structure on the hyperbranched silicon-containing acrylate monomer.
peak 1(δ ═ 5.76 to 6.80ppm, CH2CHCOO-) and peak (2+3+4+5) [ delta ] 4.07-4.47ppm, OC (OCH)2CH2)3]By integrating the peak areas, it can be calculated that the ratio of the peak areas is 1.19/4, relative to the ratio of the structural formulae of the two monomers before reaction is 3/4, which means that 39.7% of the acrylate structure is reacted onto the hyperbranched silicon-containing acrylate monomer. Peak 9(δ 1.43-1.75ppm, NCH) is present2CH2CH2Si) and peak 10(δ 0.46-0.71ppm,CH2CH2Si) which indicates Si-O-C in the structural formula2H5There was a small amount of hydrolysis.
(3) referring to FIG. 4, the average number average molecular weight of the hyperbranched silicon-containing acrylate is 3308g/mol, and the dispersity is 1.59, as seen from the GPC pattern of the hyperbranched silicon-containing acrylate in THF solution.
Therefore, the hyperbranched silicon-containing acrylate monomer prepared by the method can be used as a monomer to participate in the early photocuring reaction, and can continue the crosslinking reaction under the later-stage moisture condition, so that the adhesive strength of the adhesive film at the black edge of the display screen is improved.
Example 15
In this embodiment 15, hot melt adhesive films (films prepared by tape casting) are respectively prepared by using the hyperbranched silicon-containing acrylate monomers obtained in the embodiments 4 to 9 as main raw materials, and then performance tests are performed, wherein the specific operation processes are as follows:
(1) And (5) testing the bonding strength.
the sample preparation method comprises the following steps: laminating according to the mode of ultrawhite glass/hot melt adhesive film/polyethylene glycol terephthalate film, wherein half area is shielded by black adhesive tape, and vacuumizing is carried out in a laminator at the temperature of 80 ℃ to finish prepressing lamination. One sample was cured under irradiation with a UV mercury lamp. After the other sample was cured by irradiation of a UV mercury lamp, the moisture curing was continued at a temperature of 23. + -. 1 ℃ and a relative humidity of 50. + -. 5% RH.
And (3) testing conditions are as follows: the temperature is 23 +/-5 ℃, and the relative humidity is 50 +/-20% RH.
And (3) performance characterization: the test was carried out according to GB/T2790-1995 test method for 180 ℃ peel strength of adhesives for Flexible versus rigid materials.
(2) and (5) performing constant temperature and humidity test.
The sample preparation method comprises the following steps: the hot melt adhesive film is clamped by two pieces of ultra-white glass with black frames, the laminating machine with 80 ℃ is vacuumized to complete prepressing and laminating, and UV curing and moisture curing are carried out firstly.
and (3) testing conditions are as follows: the temperature is 85 ℃, the humidity is 85 percent, and the time is 500 h.
And (3) performance characterization: the yellowing index (Delta YI) is tested according to GB 2409-80 national standard 'test method for yellow index of plastics'.
(3) And (4) performing a cold and hot impact test.
The sample preparation method comprises the following steps: laminating according to the mode of a glass cover plate/a hot melt adhesive film/a sensor, vacuumizing a laminating machine at the temperature of 80 ℃ to finish prepressing and laminating, and performing UV curing and then moisture curing.
And (3) testing conditions are as follows: 30min/90 ℃ at-40 ℃ and 30min X200 cycles.
And (3) performance characterization: the appearance was observed.
(4) Ultraviolet aging yellowing test.
The sample preparation method comprises the following steps: laminating according to the mode of a glass cover plate/a hot melt adhesive film/a sensor, vacuumizing a laminating machine at the temperature of 80 ℃ to finish prepressing and laminating, and performing UV curing and then moisture curing.
And (3) testing conditions are as follows: UVA-340nm, UVB-313nm, 60 +/-5 ℃ and 15kwh/m2。
And (3) performance characterization: the yellowing index (Delta YI) is tested according to GB 2409-80 national standard 'test method for yellow index of plastics'.
The test results are shown in table 1: the curing energy and the moisture curing time of the UV and moisture dual-curing hot melt adhesive film prepared by the invention can be adjusted, the adhesive film can be cured in the shaded shadow part through moisture, and the adhesive film has excellent bonding strength, humidity and heat aging resistance, cold and heat shock resistance and ultraviolet aging resistance.
TABLE 1 results of testing the Properties of the Hot-melt adhesive films
In conclusion, the acrylate monomer, the synthesis method thereof and the UV and moisture dual-curing hot melt adhesive film of the invention, the method takes triacrylate as a raw material, utilizes amino double bond Michael addition reaction to prepare a synthesized hyperbranched silicon-containing acrylate monomer in one step, further prepares a hot melt adhesive film suitable for UV and/or moisture dual curing, facilitates the adhesive film to be cured under the condition of no UV light irradiation and under the condition of sustainable moisture and heat, improves the peel strength of the black edge part of the touch screen, can provide effective protection for the touch screen in the field with the black edge, ensures that the adhesive film is completely cured in the shielded shadow part, solves the packaging problem of the touch screen, can realize curing by UV and/or moisture, and also has excellent performances in the aspects of bonding strength, moisture and heat aging resistance, cold and hot shock resistance, ultraviolet aging resistance and the like, the packaging requirements of various touch screens can be met, and the packaging requirements of the touch screens with the oversized sizes are particularly suitable.
in light of the foregoing description of the preferred embodiment of the present invention, many modifications and variations will be apparent to those skilled in the art without departing from the spirit and scope of the invention. The technical scope of the present invention is not limited to the content of the specification, and must be determined according to the scope of the claims.
Claims (8)
1. A hyperbranched silicon-containing acrylate monomer has a structural formula as follows:
Wherein
R1Is CH2-CH2-Si(OMe)3。
2. The hyperbranched silicon-containing acrylate monomer of claim 1,
R2Is H or CH3。
3. A method for synthesizing hyperbranched silicon-containing acrylate monomer is characterized by comprising the following steps:
Mixing KH550, triacrylate and sodium alkoxide in an organic solvent;
Heating for reaction;
Filtering and washing; and
drying and purifying to obtain the hyperbranched silicon-containing acrylate monomer.
4. The method of synthesis according to claim 3,
The reaction formula of the heating reaction is as follows:
5. The method of synthesis according to claim 3,
the molar ratio of the KH550 to the triacrylate to the sodium alkoxide is 1: 1-3: 0.005-0.01.
6. The method of synthesis according to claim 3,
The organic solvent includes: one or more of THF, dichloromethane, dioxane and ethyl formate.
7. The method of synthesis according to claim 3,
The triacrylate comprises any one or a mixture of glycerol triacrylate and trimethylolpropane triacrylate.
8. A UV moisture dual-curing hot melt adhesive film is characterized in that,
The hot melt adhesive film is suitable for being prepared by using the hyperbranched silicon-containing acrylate monomer as claimed in claim 1 as a main raw material.
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US20070264440A1 (en) * | 2004-10-06 | 2007-11-15 | Kansai Paint Co., Ltd. | Active Energy Ray-Curable Coating Composition and Method for Forming Coating Film |
CN101665561A (en) * | 2009-09-10 | 2010-03-10 | 恒昌涂料(惠阳)有限公司 | Siloxane modified urethane acrylate hyperbranched oligomer and preparation method thereof and multi-curing coating obtained therefrom |
CN106928467A (en) * | 2017-04-19 | 2017-07-07 | 珠海飞扬新材料股份有限公司 | A kind of synthetic method of acrylate of ultraviolet light polymerization and application |
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US20070264440A1 (en) * | 2004-10-06 | 2007-11-15 | Kansai Paint Co., Ltd. | Active Energy Ray-Curable Coating Composition and Method for Forming Coating Film |
CN101665561A (en) * | 2009-09-10 | 2010-03-10 | 恒昌涂料(惠阳)有限公司 | Siloxane modified urethane acrylate hyperbranched oligomer and preparation method thereof and multi-curing coating obtained therefrom |
CN106928467A (en) * | 2017-04-19 | 2017-07-07 | 珠海飞扬新材料股份有限公司 | A kind of synthetic method of acrylate of ultraviolet light polymerization and application |
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