CN114045139A - Electric corrosion resistant ultraviolet curing adhesive and preparation method thereof - Google Patents
Electric corrosion resistant ultraviolet curing adhesive and preparation method thereof Download PDFInfo
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- CN114045139A CN114045139A CN202111390159.5A CN202111390159A CN114045139A CN 114045139 A CN114045139 A CN 114045139A CN 202111390159 A CN202111390159 A CN 202111390159A CN 114045139 A CN114045139 A CN 114045139A
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- acrylate
- electric corrosion
- ultraviolet curing
- modified silicon
- constant temperature
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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
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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
- 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
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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
- C09J167/00—Adhesives based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Adhesives based on derivatives of such polymers
- C09J167/06—Unsaturated polyesters having carbon-to-carbon unsaturation
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Abstract
The invention discloses an electric corrosion resistant ultraviolet curing adhesive and a preparation method thereof, belonging to the technical field of curing adhesive design. The electric corrosion resistant ultraviolet curing adhesive comprises the following components in percentage by weight: 10-25% of acrylate oligomer, 15-30% of modified silicon-containing polyurethane acrylate, 10-25% of active monomer, 1-5% of coupling agent, 10-30% of diluent, 5-10% of photoinitiator and 1-10% of leveling agent. According to the invention, by adding the modified silicon-containing urethane acrylate, the adhesion amount of water molecules can be reduced, the problem of electric corrosion of the glue under the conditions of high temperature and high humidity is effectively solved, the adhesion performance is good, the required curing energy is low, the curing speed is high, and the glue is more green and environment-friendly.
Description
Technical Field
The invention relates to the technical field of curing adhesive design, in particular to an electric corrosion resistant ultraviolet curing adhesive and a preparation method thereof.
Background
The ultraviolet curing adhesive is also called UV adhesive and shadowless adhesive, is an acrylate adhesive which can be cured by ultraviolet rays/visible light, and has the characteristics of high efficiency, energy conservation, environmental protection and the like. However, with the development and development of technology, the requirements of LCD and TFT industries on panel adhesion are increasing, which puts higher demands on UV adhesives. The existing UV glue on the market needs to measure the performance of the glue through tests of shear strength, tensile strength, peeling strength, impact strength, elongation at break, aging performance and the like. The aging performance is divided into high and low temperature impact test, chemical resistance test, electric corrosion resistance test, rapid ultraviolet aging, mercury lamp aging, salt fog aging, and appearance and performance evaluation after aging, and the problem of electric corrosion resistance is mainly aimed at this time. In the manufacturing process, an automatic glue dispenser is generally adopted to uniformly coat UV glue on the STN glass tube pin; the exposure energy of the cold light source LED lamp is about 2000mJ/cm2The mercury lamp exposure is divided into an upper light source and a lower light source, the energy of the upper light source is 600-2The lower light source energy is about 1000mJ/cm2(ii) a Secondly, coating black silica gel on the integrated position of the circuit, wherein the main purpose is to protect the circuit; and finally, fixing the PIN PIN on the glass, and performing gap glue filling (UV glue) on the contact surface of the PIN PIN and the surface of the glass. After leveling, the UV glue and the black silica gel are contacted, and when the power-on test is carried out for 600-700h under the conditions of high temperature and high humidity (85 ℃, 85% RH), moisture in the air can enter gaps, so that the circuit corrosion is caused. After the circuit is corroded, the phenomena of short circuit, open circuit, dislocation and the like of glass display can be causedEven the use effect of the product is seriously affected by the bright lines, abnormal display and the like.
Therefore, the research on the UV adhesive capable of solving the problem of the electric corrosion is of great significance.
Disclosure of Invention
The invention aims to provide an electric corrosion resistant ultraviolet curing glue and a preparation method thereof, and mainly aims to improve the adhesive property of silica gel, reduce the required curing energy and effectively solve the electric corrosion problem of the glue under the conditions of high temperature and high humidity by adding modified silicon-containing urethane acrylate for formula blending.
In order to solve the problems, the invention adopts the following technical scheme:
an electric corrosion resistant ultraviolet curing adhesive comprises the following components: according to the weight percentage, 10-25% of acrylate oligomer, 15-30% of modified silicon-containing polyurethane acrylate, 10-25% of active monomer, 1-5% of coupling agent, 10-30% of diluent, 5-10% of photoinitiator and 1-10% of flatting agent, wherein the sum of the weight percentages of the components is 100%.
The acrylate oligomer is one or a combination of epoxy acrylate, polyester acrylate, polyether acrylate, polybutadiene acrylate, polyurethane acrylate and pure acrylate.
The structure of the modified silicon-containing polyurethane acrylate is as follows:
wherein n is 2-10, and R is one of methyl, ethyl, hydroxyl and ethoxy.
The preparation method of the modified silicon-containing polyurethane acrylate comprises the following steps:
(1) synthesis of intermediate I
And (3) adding the reactant B into a three-neck flask provided with a stirrer, a condenser tube, a drying tube and a dropping funnel, heating to 70 ℃, stirring, dropwise adding the reactant A, continuously reacting for 2 hours after dropwise adding for about 1 hour to obtain an intermediate I.
(2) Synthesis of modified silicon-containing urethane acrylate A
Adding the reactant C into a three-neck flask, adding dimethylbenzene, uniformly stirring, heating to 50 ℃, dropwise adding the intermediate I into a reaction system, completing the addition for about 40min, heating to 70 ℃, continuing to react for 2h to obtain a polyurethane prepolymer with a terminal-NCO group, adding the reactant D and triethylamine accounting for 0.1% of the mass of the reactant, and reacting at constant temperature for 12h to obtain the modified silicon-containing polyurethane acrylate A.
The active monomer is one or a combination of methacrylate, hydroxyethyl methacrylate, trimethylolpropane trimethacrylate, polypropylene glycol dimethacrylate, isooctyl acrylate, isobornyl acrylate, hydroxyalkyl (meth) acrylate and 2-phenoxyethyl acrylate.
The coupling agent is one of vinyl trimethoxy silane, 3- (phenylamino) propyl trimethoxy silane, gamma-glycidyl ether oxypropyl methyl diethoxy silane, vinyl trichlorosilane, gamma-glycidyl oxy propyl trimethoxy silane, gamma-methacryloxy propyl trimethoxy silane and triethoxymethyl silane.
The diluent is one or more of TPGDA, IDA, PDDA, HPA, BDDA, HEMA and NPGDA.
The photoinitiator is one or a mixture of more of OMBB, PBZ, CBP, TPO, EDB, ITX, 907, 184 and EDAB.
The flatting agent is one of phosphate modified acrylic acid, polybutyl acrylate, poly (2-ethylhexyl acrylate), ethyl acrylate, butyl acrylate and polysiloxane.
The preparation method of the electric corrosion resistant ultraviolet curing adhesive comprises the following steps: firstly, putting an acrylate oligomer, modified silicon-containing polyurethane acrylate and an active monomer into an oven, heating for 5 hours at a constant temperature of 65 ℃ for later use; then sequentially adding the heated acrylate oligomer, the modified silicon-containing polyurethane acrylate, the active monomer and the diluent into a reaction kettle, and stirring for 10min at the constant temperature of 50 ℃; then adding the coupling agent, the photoinitiator and the flatting agent in sequence, stirring for 30min at the constant temperature of 50 ℃, taking out the reaction kettle, placing the reaction kettle into an oven at the constant temperature of 65 ℃, standing for 30min, continuing stirring for 30min at the constant temperature of 50 ℃ by using a stirrer, standing and cooling to room temperature to obtain the nano-silver/nano-silver.
The invention has the following remarkable advantages:
the modified silicon-containing urethane acrylate can improve the compatibility with silica gel or organic silicon materials, and overcome the problem that the physical mixing method cannot achieve the expected effect. By introducing the organic silicon chain segment, the molecular molar volume is increased, the cohesive energy density is low, and the surface tension is reduced, so that the excellent hydrophobic property can be endowed to the organic silicon chain segment, and meanwhile, the chain segment has good compatibility with silica gel, and the adhesive force of the ultraviolet curing adhesive to the silica gel can be improved. And secondly, the dielectric constant can be improved by introducing carbonyl groups into side chains, so that the insulativity of the ultraviolet curing adhesive is enhanced. The benzene ring is adopted as the end capping treatment, so that the hydrophobic effect can be improved to a certain extent, water vapor is prevented from being condensed on the surface of the colloid, and the chemical property of the colloid is more stable from the structural angle of the benzene ring.
Drawings
FIG. 1 is a microscope image of a comparative example after an electrocorrosion test, wherein the local integrated circuit is peeled off at the marked position, i.e. electrocorrosion phenomenon.
FIG. 2 is a microscope image of an electro-corrosion test showing the integrated circuit without peeling off according to an embodiment.
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 the exemplary embodiments and descriptions thereof are only used for explaining the present invention and are not meant to limit the present invention.
The preparation method of the modified silicon-containing polyurethane acrylate comprises the following steps:
(1) synthesis of intermediate I
In a three-neck flask equipped with a stirrer, a condenser tube, a drying tube and a dropping funnel, hydroxyethyl acrylate is firstly added, the temperature is raised to 70 ℃, 3-aminopropyltriethoxysilane is stirred and dropwise added, and the addition amount of the hydroxyethyl acrylate and the 3-aminopropyltriethoxysilane is added according to the molar ratio of 1: 1. After about 1h of dropwise addition, the reaction was continued for 2h to obtain intermediate I.
(2) Synthesis of modified silicon-containing urethane acrylate A
Adding toluene-2, 4-diisocyanate and xylene into a three-neck flask according to the mass ratio of 1:1, stirring uniformly, heating to 50 ℃, dropwise adding the intermediate I into a reaction system, completing the addition for about 40min, heating to 70 ℃, continuing to react for 2h to obtain a polyurethane prepolymer with a terminal-NCO group, then adding p-methyl phenol and triethylamine accounting for 0.1% of the mass of the reaction, and reacting at constant temperature for 12h to obtain the modified silicon-containing polyurethane acrylate A.
According to1H NMR (delta, DMSO,300MHz) analysis with a chemical shift (delta) of 1.21(t,18H, CH2-CH 3); 1.85(m,8H, CH2-CH2-CH 2); 2.19(s,24H, C-CH 3); 2.35(t,8H, CH2-CH 2-C); 2.46(t,4H, CH2-CH 2-N); 3.76(t,8H, N-CH2-CH 2); 4.28(d,8H, CH-CH 2-OH); 7.36(d,2H, C ═ CH-C); 7.72(s,4H, C ═ CH-C); 9.86(s,8H, C-NH-C).
The successful synthesis of the modified silicon-containing urethane acrylate in which n is 3 and R is methyl is illustrated.
Examples and comparative examples: an ultraviolet curing adhesive with electric corrosion resistance.
The high temperature resistant UV adhesives of the examples and comparative examples were prepared according to the compositions and mass percentages shown in the following Table 1, and the units of the parts may be gram, kilogram, ton or other weight units. The specific preparation process comprises the following steps: firstly, putting an acrylate oligomer, modified silicon-containing polyurethane acrylate and an active monomer into an oven, heating for 5 hours at a constant temperature of 65 ℃ for later use; then sequentially adding the heated acrylate oligomer, the modified silicon-containing polyurethane acrylate, the active monomer and the diluent into a reaction kettle, and stirring for 10min at the constant temperature of 50 ℃; and then adding the coupling agent, the photoinitiator and the flatting agent in sequence, stirring for 30min at the constant temperature of 50 ℃, taking out the reaction kettle, placing the reaction kettle into an oven at the constant temperature of 65 ℃, standing for 30min, continuing stirring for 30min at the constant temperature of 50 ℃ by using a stirrer, standing and cooling to room temperature.
Testing of the R group of the modified silicon-containing urethane acrylate with methyl, PmThe number of carbon on the long chain of the modified silicon-containing urethane acrylate is m, and m is 3-10.
TABLE 1 (the content units in the tables are in parts by weight)
Experimental example: measurement experiment of ultraviolet curing adhesive performance
In order to evaluate the electric corrosion performance of the above examples 1 to 4 and comparative examples 1 to 4, the adhesion performance test and the electric corrosion test of the uv curable adhesive were performed by the following experiments.
1. Adhesion Performance test
Clamping the PIN PIN on a glass substrate, coating ultraviolet light curing glue on the front and back sides of the contact surface of the PIN PIN and the glass by using a glue dispenser, placing the coated PIN PIN and the glass into an ultraviolet light curing tester for light curing, and controlling the curing energy to be 1200mJ/cm2(ii) a The glass substrate is taken out, put into a water bath kettle and boiled for 12h at constant temperature of 100 ℃, then a tension meter is adopted to carry out tension test, 15 tension test experiments are carried out on each embodiment and comparative example, and the average value is taken for recording.
2. Electrocorrosion test
Coating a layer of black silica gel on the step of the glass substrate, clamping the PIN PIN on the glass substrate after the natural surface is dried, coating ultraviolet light curing glue on the front and back surfaces of the contact surface of the PIN PIN and the glass by using a glue dispenser, placing the glass substrate in an ultraviolet light curing tester for light curing, wherein the curing energy isControlling the amount to 1000mJ/cm2(ii) a Taking out the glass substrate, putting the glass substrate into a constant temperature and humidity box, and carrying out an electrifying test on the glass by externally connecting an electrode under the conditions of 85 ℃ and 85% RH, wherein the test period is 700 h. And taking out the glass substrate, tearing off the attached ultraviolet curing glue and black silica gel, wiping the contact position of the ultraviolet curing glue and the black silica gel back and forth for a plurality of times by using dust-free cloth, observing the electric corrosion degree by using a metallographic microscope, and respectively showing pictures of the first comparative example and the first example after the electric corrosion test as shown in figures 1 and 2.
TABLE 2
As can be seen from Table 2, the adhesion and the electric corrosion resistance of comparative example No. III are the worst, and the tensile value and the electric corrosion resistance effect after boiling in water for 12h are lower than those of other examples. On the whole, after the test, the tensile value after the water boiling for 12 hours in the examples is 4.3-4.9 kg, and the electric corrosion resistance effect is excellent, while the tensile value after the water boiling in the comparative examples is 1.9-3.1 kg, wherein the electric corrosion resistance performance of the comparative example I and the comparative example IV is general, and the electric corrosion resistance performance of the comparative example II and the comparative example III is poor. The main reason is that the third comparative example has no modified silicon-containing urethane acrylate, so that the adhesion and the electric corrosion resistance are seriously reduced; secondly, the second comparative example reduces the amount of P5 and properly increases the amount of polyester acrylate, so that the experimental result is substantially the same as that of the third comparative example. Experiments show that the modified silicon-containing polyurethane acrylate can play a significant role in the electrical corrosion performance, can ensure the adhesiveness of the colloid, and is low in required curing energy, high in curing speed and more environment-friendly.
Finally, it should be noted that: the above embodiments describe the present invention in detail, but they are only examples and do not limit the scope of the invention. All equivalent modifications and substitutions made by the present specification are within the scope of the present invention and are included in the patent protection scope of the present invention.
Claims (9)
1. The electric corrosion resistant ultraviolet curing adhesive is characterized by comprising the following components in percentage by weight: 10-25% of acrylate oligomer, 15-30% of modified silicon-containing polyurethane acrylate, 10-25% of active monomer, 1-5% of coupling agent, 10-30% of diluent, 5-10% of photoinitiator and 1-10% of leveling agent, wherein the sum of the weight percentages of the components is 100%.
2. The ultraviolet curing glue capable of resisting electric corrosion according to claim 1, wherein the acrylate oligomer is one or a combination of epoxy acrylate, polyester acrylate, polyether acrylate, polybutadiene acrylate, polyurethane acrylate and pure acrylate.
3. The ultraviolet-curable adhesive capable of resisting electric corrosion according to claim 1, wherein the modified silicon-containing urethane acrylate has the following structure:
wherein n =2-10, and R is one of methyl, ethyl, hydroxyl and ethoxy.
4. The ultraviolet light curing glue capable of resisting electric corrosion according to claim 1, wherein the active monomer is one or a combination of methacrylate, hydroxyethyl methacrylate, trimethylolpropane trimethacrylate, polypropylene glycol dimethacrylate, isooctyl acrylate, isobornyl acrylate, hydroxyalkyl (meth) acrylate and 2-phenoxyethyl acrylate.
5. The ultraviolet curing glue capable of resisting electrolytic corrosion according to claim 1, wherein the coupling agent is one of vinyltrimethoxysilane, 3- (phenylamino) propyltrimethoxysilane, gamma-glycidoxypropylmethyldiethoxysilane, vinyltrichlorosilane, gamma-glycidoxypropyltrimethoxysilane, gamma-methacryloxypropyltrimethoxysilane and triethoxymethylsilane.
6. The ultraviolet-curable glue capable of resisting electric corrosion according to claim 1, wherein the diluent is one or more of TPGDA, IDA, PDDA, HPA, BDDA, HEMA and NPGDA.
7. The ultraviolet curing glue capable of resisting electric corrosion according to claim 1, wherein the photoinitiator is one or a mixture of OMBB, PBZ, CBP, TPO, EDB, ITX, 907, 184 and EDAB.
8. The ultraviolet curing adhesive of claim 1, wherein the leveling agent is one of phosphate ester modified acrylic acid, polybutyl acrylate, poly 2-ethylhexyl acrylate, ethyl acrylate, butyl acrylate and polysiloxane.
9. The method for preparing the ultraviolet curing adhesive with the electric corrosion resistance according to any one of claims 1 to 8, wherein the method comprises the following steps: firstly, putting an acrylate oligomer, modified silicon-containing polyurethane acrylate and an active monomer into an oven, heating for 5 hours at a constant temperature of 65 ℃ for later use; then sequentially adding the heated acrylate oligomer, the modified silicon-containing polyurethane acrylate, the active monomer and the diluent into a reaction kettle, and stirring for 10min at the constant temperature of 50 ℃; then adding the coupling agent, the photoinitiator and the flatting agent in sequence, stirring for 30min at the constant temperature of 50 ℃, taking out the reaction kettle, placing the reaction kettle into an oven at the constant temperature of 65 ℃, standing for 30min, continuing stirring for 30min at the constant temperature of 50 ℃ by using a stirrer, standing and cooling to room temperature to obtain the nano-silver/nano-silver.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115678487A (en) * | 2022-12-30 | 2023-02-03 | 烟台泰盛精化科技有限公司 | Ultraviolet light curing adhesive and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1974580A (en) * | 2006-12-06 | 2007-06-06 | 华南理工大学 | Prepn process of acrylate modified gamma-aminopropyl triethoxysilane |
| CN107011852A (en) * | 2017-05-23 | 2017-08-04 | 句容耀皮节能玻璃科技发展有限公司 | A kind of mould proof photocuring vehicle glass renovation agent and preparation method thereof |
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2021
- 2021-11-23 CN CN202111390159.5A patent/CN114045139A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1974580A (en) * | 2006-12-06 | 2007-06-06 | 华南理工大学 | Prepn process of acrylate modified gamma-aminopropyl triethoxysilane |
| CN107011852A (en) * | 2017-05-23 | 2017-08-04 | 句容耀皮节能玻璃科技发展有限公司 | A kind of mould proof photocuring vehicle glass renovation agent and preparation method thereof |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115678487A (en) * | 2022-12-30 | 2023-02-03 | 烟台泰盛精化科技有限公司 | Ultraviolet light curing adhesive and preparation method thereof |
| CN115678487B (en) * | 2022-12-30 | 2023-04-07 | 烟台泰盛精化科技有限公司 | Ultraviolet light curing adhesive and preparation method thereof |
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