CN110922926B - Low-temperature cured single-component transparent epoxy glue and preparation method and application thereof - Google Patents
Low-temperature cured single-component transparent epoxy glue and preparation method and application thereof Download PDFInfo
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- CN110922926B CN110922926B CN201911256647.XA CN201911256647A CN110922926B CN 110922926 B CN110922926 B CN 110922926B CN 201911256647 A CN201911256647 A CN 201911256647A CN 110922926 B CN110922926 B CN 110922926B
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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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/66—Mercaptans
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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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/10—Transparent films; Clear coatings; Transparent materials
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention discloses a low-temperature cured single-component transparent epoxy glue and a preparation method and application thereof, wherein the glue is prepared from the following raw materials in percentage by weight: 15-35% of aliphatic epoxy resin, 25-45% of polyurethane modified epoxy resin, 25-45% of polythiol curing agent, 2.5-4.5% of accelerator and 1.4-2.2% of stabilizer. The low-temperature cured single-component transparent epoxy glue disclosed by the invention has the following characteristics: low-temperature rapid curing (can meet the curing condition of 10min @80 ℃); the single component is convenient to use; good flexibility and cold and hot shock aging resistance; colorless and transparent, and does not yellow after aging; the operation time is long, and the use can be continued for 5 days. The low-temperature cured single-component transparent epoxy glue can be effectively used for bonding transparent materials or bonding the transparent materials with opaque metal, ceramic and resin, and the glue layer is colorless and transparent and does not influence the transmission of optical signals.
Description
Technical Field
The invention relates to the field of electronic glue, in particular to single-component transparent epoxy glue with cold and heat shock aging resistance, heat and humidity aging resistance and low-temperature curing performance, and a preparation method and application thereof.
Background
More and more electronic devices are now equipped with displays, while many control elements are implemented inside the glass cover of the display, such as the optical fingerprint of the next generation of mobile phones. The glue for assembling the components is required to be transparent after being cured, and is not atomized or yellowed after being aged by damp and heat, so that the light transmittance and the appearance are influenced. Also, because some components attached to the object to be bonded may not be able to withstand too high a temperature, it is necessary that the glue be cured quickly at a low temperature. In addition, the glue must have certain toughness after being cured and can resist cold and hot impact aging. Moreover, if the single-component polyurethane foam can be prepared into a single component, premixing of the AB component is not needed during use, and the use is more convenient and faster. Therefore, there is an increasing demand for one-component transparent glues that can be cured at low temperatures that simultaneously satisfy the above conditions.
At present, most of glue with good transparency and without atomization and yellowing after aging adopts an organic silicon resin system, mainly because the glue has the characteristics of transparency and aging resistance and flexibility, but the glue has a fatal defect that the glue cannot be reinforced by adding filler because the glue is required to be transparent, the bonding strength is not high under the condition, the glue cannot meet the requirement for bonding structural parts with high bonding force, and the glue has limitation in use. In order to obtain the single-component transparent glue with high cohesive force, an epoxy resin system is preferably selected. In the prior art, the most common bisphenol A epoxy resin in the epoxy resin is not resistant to yellowing, mainly because methyl groups on two sides in a bisphenol A structure fall off after aging, so that the colloid is yellow. There is also a class of epoxy resins that do not contain bisphenol a structures, commonly referred to as aliphatic epoxy resins, which remain stable in molecular structure, transparent in colloid, and non-yellowing in color upon aging, and thus are widely used in transparent high strength adhesives. However, glues made with aliphatic epoxy resins alone are hard and brittle and do not resist thermal shock aging.
Disclosure of Invention
The purpose of the invention is as follows: the invention is completed in view of the current situation that the market demands for single-component transparent glue with cold and heat shock aging resistance, damp and heat aging resistance and low-temperature curing are gradually increased and the glue which actually meets the conditions is few. Aiming at the problems in the prior art, the invention provides a low-temperature cured single-component transparent epoxy glue, which solves the following problems of single-component transparent glue: (1) the bonding strength of the transparent organic silicon glue is not high; (2) the transparent epoxy glue has poor toughness and is not resistant to cold and hot shock aging; (3) the transparent epoxy glue turns yellow or the transparency is reduced after humid heat aging. The following purposes are achieved: the single-component transparent epoxy glue cured at low temperature is provided, and has the following characteristics: (1) single components; (2) the colloid is colorless and transparent; (3) low-temperature rapid curing (can meet the curing condition of 10min @80 ℃); (4) the colloid has good flexibility and can resist cold and hot impact of-40 ℃ to 85 ℃ for 200 times; (5) the colloid does not turn yellow and the transparency does not decrease after aging for 1000h at the high temperature of 85 ℃ and the humidity of 85 percent; (6) the operation time is long, and the use can be continued for 5 days; (7) the adhesive can be used for bonding transparent glass or transparent resin materials, and can also be used for bonding transparent materials and non-transparent materials such as metal, ceramic, resin and the like.
In order to solve the above problems, the present invention is repeatedly tested and tested, and the final technical solution is as follows: aliphatic epoxy resin and polyurethane modified epoxy resin are mixed, polythiol is used as a curing agent, and a certain amount of stabilizing agent is matched to prepare glue meeting the requirements.
Based on the technical scheme, the detailed solution of the invention is as follows:
the low-temperature cured single-component transparent epoxy glue is prepared from the following raw materials in percentage by weight: 15-35% of aliphatic epoxy resin, 25-45% of polyurethane modified epoxy resin, 25-45% of polythiol curing agent, 2.5-4.5% of accelerator and 1.4-2.2% of stabilizer.
Wherein the aliphatic epoxy resin is selected from one of 3, 4-epoxycyclohexylmethyl formate-3 ', 4' -epoxycyclohexylmethyl adipate, bis ((3, 4-epoxycyclohexyl) methyl) adipate and poly [ (2-oxiranyl) -1, 2-cyclohexanediol ] 2-ethyl-2- (hydroxymethyl) -1, 3-propanediol ether.
Wherein the polyurethane modified epoxy resin is selected from one of EPU-133T, SL-3413 or 102-C.
Wherein the polythiol curing agent is one selected from pentaerythritol tetrakis (3-mercaptopropionate) (PETMP), trimethylolpropane tris (3-mercaptopropionate) (TMPMP), ethylene glycol bis (3-mercaptopropionate) (GDMP), pentaerythritol tetrakis (thioglycolate) ester (PETMA), or trimethylolpropane tris (3-Thioglycolate) (TMPMA).
Wherein the promoter is selected from one of PN-23J, MY-24, EH-4360S, EH-3615S or EH-4070S.
Wherein the stabilizer is selected from ICAM-8402, HSCHEM-3200, or VT-1010.
The preparation method of the single-component transparent epoxy glue cured at low temperature comprises the following steps: mixing aliphatic epoxy resin, polyurethane modified epoxy resin, polythiol curing agent and stabilizing agent, uniformly stirring them, adding accelerating agent, secondary stirring, uniformly mixing them, vacuum-pumping and defoaming so as to obtain the invented product.
The low-temperature cured single-component transparent epoxy glue is applied to bonding of transparent materials or bonding of transparent materials and opaque materials, and the glue layer is colorless and transparent and does not influence transmission of optical signals.
Wherein the transparent material comprises transparent glass or a transparent resin material, and the non-transparent material comprises metal, ceramic, or resin.
The bisphenol A epoxy resin which is most commonly used in the epoxy resin is not adopted in the invention, mainly because methyl groups on two sides in a bisphenol A structure can fall off after aging, so that the colloid is yellow. But epoxy resins not having a bisphenol a structure, generally called aliphatic epoxy resins, which are stable in molecular structure, transparent in colloid, and not yellow in color upon aging, are widely used in transparent high-strength adhesives. However, the glue water made of the aliphatic epoxy resin is hard and brittle, and does not resist cold and hot shock aging, so that the polyurethane modified epoxy resin is added with other components for toughening, the resin structure of the glue water has the epoxy group for providing bonding capability, the polyurethane chain segment for providing flexibility, and the glue water has good intermiscibility with the aliphatic epoxy resin.
Has the advantages that: compared with the prior art, the invention has the following advantages:
the low-temperature cured single-component transparent epoxy glue disclosed by the invention contains 15-35% of aliphatic epoxy resin and 25-45% of polyurethane modified epoxy resin. Because the epoxy resin has excellent bonding performance for various metal materials and non-metal materials, and is called as a universal adhesive, the adhesive of the invention has high bonding strength and is suitable for bonding various materials. And because of the toughening effect of the polyurethane modified epoxy resin, the glue disclosed by the invention is good in toughness and resistant to cold and hot shock. And the two epoxy resins keep stable structure when aging, so that the glue disclosed by the invention is high in transparency, free from yellowing and resistant to damp-heat aging.
The low-temperature cured single-component transparent epoxy glue disclosed by the invention contains 25-45% of polythiol curing agent and 2.5-4.5% of accelerator. Because the composition of the polythiol and the accelerator is a low-temperature rapid curing agent of the epoxy resin, the glue disclosed by the invention has the characteristic of low-temperature rapid curing.
The low-temperature cured single-component transparent epoxy glue disclosed by the invention contains 1.3-2.2% of a stabilizer. Because the invention carries out a great deal of tests on the types and the adding amount of the stabilizer and selects the optimal scheme, the glue can ensure enough operable time even if the glue is made into a single component.
The invention has simple production process and high efficiency, and can be produced and applied in large scale. The low-temperature cured single-component transparent epoxy glue can be effectively used for bonding transparent materials (glass or resin) or bonding the transparent materials with opaque metal, ceramic and resin, and the glue layer is colorless and transparent and does not influence the transmission of optical signals.
Detailed Description
The technical solution of the present invention will be described below with reference to specific examples.
The starting materials and reagents used in the present invention are commercially available. The specific raw materials used in examples 1 to 6 and comparative examples 1 to 2 are as follows:
TABLE 1
The raw materials and the amounts (wt%) used in examples 1 to 3 and comparative example 1 are shown in Table 2;
TABLE 2
The raw materials and amounts (wt%) used in examples 4 to 6 and comparative example 2 are shown in Table 3:
TABLE 3
Embodiment 1-6 preparation of single-component transparent epoxy glue cured at low temperature:
mixing aliphatic epoxy resin, polyurethane modified epoxy resin, polythiol curing agent and stabilizer according to the proportion in the table 2 and the table 3, uniformly stirring, adding accelerator, performing secondary stirring, uniformly mixing, and performing vacuum-pumping defoaming to complete the preparation.
Comparative example 1
The difference between the comparative example 1 and the example 3 is that the aliphatic epoxy resin TTA-3150 is replaced by bisphenol A epoxy resin E-03 with equal amount, other materials and mixture ratio are not changed, and the preparation method is also not changed.
Comparative example 2
The difference between the comparative example 2 and the example 6 is that the polyurethane modified epoxy resin is not added as a toughening agent, namely the polyurethane modified epoxy resin 102-C is replaced by the same amount of aliphatic epoxy resin TTA-3150, other materials and mixture ratio are not changed, and the preparation method is also not changed.
Test example
The single-component transparent epoxy glue obtained in examples 1 to 6 and comparative examples 1 to 2 was subjected to the basic performance test of table 4 below and the aging performance test of table 5 below:
TABLE 4 basic Performance test
TABLE 5 aging resistance test
| Serial number | Test items | Test method |
| 1 | Aging by moist heat | Adhesion, light transmittance and yellowness index after 1000h of high temperature and humidity (85 ℃/85% RH) |
| 2 | Cold and hot shock aging | Testing the cohesive force, the light transmittance and the yellow index after 200 times of cold and hot alternating impact at the temperature of between 40 ℃ below zero and 85 DEG C |
The results of the basic performance tests are shown in table 6:
TABLE 6 basic Performance test data List
| Examples | Curing conditions | Adhesive force | Operational time | Light transmittance after curing | Yellowness index after curing |
| Example 1 | 7min@80℃ | 6.0mPa | 9 days | 99.1％ | 1.2 |
| Example 2 | 7min@80℃ | 7.1mPa | 9 days | 99.3％ | 1.1 |
| Example 3 | 6min@80℃ | 8.4mPa | 7 days | 99.2％ | 0.9 |
| Comparative example 1 | 6min@80℃ | 8.3mPa | 7 days | 96.1％ | 3.2 |
| Example 4 | 9min@80℃ | 8.8mPa | 15 days | 99.0％ | 0.8 |
| Example 5 | 7min@80℃ | 7.9mPa | 9 days | 99.1％ | 1.0 |
| Example 6 | 5min@80℃ | 7.7mPa | 5 days | 99.2％ | 1.1 |
| Comparative example 2 | 5min@80℃ | 8.9mPa | 5 days | 99.1％ | 0.9 |
And (3) data analysis: in comparison with Table 6, the results of the basic performance tests of examples 1 to 6 and comparative examples 1 to 2 are compared, and it can be seen that: (1) the light transmittance of the glue prepared in the comparative example 1 after curing is lower than that of other glue, and the yellow index is higher than that of other glue, because the bisphenol A epoxy resin is adopted in the formula of the comparative example 1, and the aliphatic epoxy resin is adopted in the formula of the examples 1-6, the light transmittance of the aliphatic epoxy resin is better, and the aliphatic epoxy resin is more resistant to yellowing; (2) the difference between the basic performance test data of the glue prepared in the comparative example 2 and the data of the glue prepared in the examples 1-6 is very small, and even the adhesion is slightly higher, mainly because the glue prepared in the comparative example 2 has higher body strength after being cured under the condition of no toughening, the adhesion is better, and the side effect of the lack of the toughening agent in the formula can be only reflected in the subsequent aging resistance test.
The aging resistance test is shown in Table 7:
TABLE 7 aging resistance test data List
And (3) data analysis: in comparison with Table 7, it can be seen from the comparison of the aging property test results of examples 1 to 6 and comparative examples 1 to 2 that: (1) compared with other cases, the light transmittance of the glue prepared in the comparative example 1 is reduced more, the yellow index is increased more, and the aging resistance is poor, because the formula of the comparative example 1 contains bisphenol A epoxy resin; (2) the difference between the light transmittance and the yellow index of the glue prepared in the comparative example 2 and those of the glue prepared in the examples 1-6 after cold-hot alternating impact aging is very small, but the adhesive force is reduced very much, and the adhesive force is much lower than that of the glue prepared in the other examples, mainly because the glue prepared in the comparative example 2 is brittle after being cured and has higher stress at a bonding part under the condition of no toughening, and the bonding part is easy to fall off after cold-hot alternating impact, so that the adhesive force is reduced.
The preferred embodiments of the present invention have been described in detail, however, the present invention is not limited to the specific details of the above embodiments, and various simple modifications may be made to the technical solution of the present invention within the technical idea of the present invention, and these simple modifications are within the protective scope of the present invention.
It should be noted that the various technical features described in the above embodiments can be combined in any suitable manner without contradiction, and the invention is not described in any way for the possible combinations in order to avoid unnecessary repetition.
In addition, any combination of the various embodiments of the present invention is also possible, and the same should be considered as the disclosure of the present invention as long as it does not depart from the spirit of the present invention.
Claims (6)
1. The low-temperature cured single-component transparent epoxy glue is characterized by being prepared from the following raw materials in percentage by weight: 15-35% of alicyclic epoxy resin, 25-45% of polyurethane modified epoxy resin, 25-45% of polythiol curing agent, 2.5-4.5% of accelerator and 1.4-2.2% of stabilizer; the alicyclic epoxy resin is selected from one of 3, 4-epoxycyclohexylmethyl formate-3 ', 4' -epoxycyclohexylmethyl ester, bis ((3, 4-epoxycyclohexyl) methyl) adipate, or poly [ (2-oxiranyl) -1, 2-cyclohexanediol ] 2-ethyl-2- (hydroxymethyl) -1, 3-propanediol ether; the polyurethane modified epoxy resin is selected from one of EPU-133T, SL-3413 or 102-C; the stabilizer is selected from one of ICAM-8402, HSCHEM-3200, or VT-1010.
2. The low-temperature-curing one-component transparent epoxy glue according to claim 1, wherein the polythiol curing agent is one selected from pentaerythritol tetrakis (3-mercaptopropionate), trimethylolpropane tris (3-mercaptopropionate), ethylene glycol bis (3-mercaptopropionate), pentaerythritol tetrakis (mercaptoacetate), and trimethylolpropane tris (3-mercaptoacetate).
3. The low temperature curing one-part transparent epoxy glue of claim 1, wherein the accelerator is selected from one of PN-23J, MY-24, EH-4360S, EH-3615S, or EH-4070S.
4. The preparation method of the low-temperature-curing single-component transparent epoxy glue disclosed by claim 1 is characterized by comprising the following steps of:
mixing alicyclic epoxy resin, polyurethane modified epoxy resin, polythiol curing agent and stabilizing agent, uniformly stirring them, adding accelerating agent, secondary stirring, uniformly mixing them, vacuum-pumping and defoaming so as to obtain the invented product.
5. The use of the low temperature curing one-component transparent epoxy glue of claim 1 in the bonding of transparent materials or the bonding of transparent materials and opaque materials.
6. The low-temperature-curing one-component transparent epoxy glue according to claim 1, wherein the transparent material comprises a transparent glass or transparent resin material, and the non-transparent material comprises a metal, a ceramic, or a resin.
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| CN106753138A (en) * | 2017-01-06 | 2017-05-31 | 上海汉司实业有限公司 | A kind of LED single-component epoxy insulation crystal-bonding adhesive and preparation method |
| CN108164979A (en) * | 2017-12-25 | 2018-06-15 | 科化新材料泰州有限公司 | A kind of polyurethane modified epoxy resin composition for semiconductor packages |
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| JP2005272647A (en) * | 2004-03-25 | 2005-10-06 | Aisin Chem Co Ltd | Structural adhesive composition |
| CN102167962B (en) * | 2011-03-22 | 2013-04-10 | 深圳市飞世尔实业有限公司 | Photocuring adhesive used for adhering optic glass lenses and preparation method thereof |
| CN104403277B (en) * | 2014-12-25 | 2018-06-08 | 无锡嘉联电子材料有限公司 | A kind of preparation method of LED encapsulation high-performance epoxy resin composition |
| EP3350275B1 (en) * | 2015-09-15 | 2020-10-21 | 3M Innovative Properties Company | An adhesive composition and an article manufactured therefrom |
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| CN106753138A (en) * | 2017-01-06 | 2017-05-31 | 上海汉司实业有限公司 | A kind of LED single-component epoxy insulation crystal-bonding adhesive and preparation method |
| CN108164979A (en) * | 2017-12-25 | 2018-06-15 | 科化新材料泰州有限公司 | A kind of polyurethane modified epoxy resin composition for semiconductor packages |
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