CN109868104B - Flexible epoxy adhesive and preparation method thereof - Google Patents
Flexible epoxy adhesive and preparation method thereof Download PDFInfo
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- CN109868104B CN109868104B CN201910149179.XA CN201910149179A CN109868104B CN 109868104 B CN109868104 B CN 109868104B CN 201910149179 A CN201910149179 A CN 201910149179A CN 109868104 B CN109868104 B CN 109868104B
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- 229920006332 epoxy adhesive Polymers 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 22
- 229920000570 polyether Polymers 0.000 claims abstract description 22
- 239000003822 epoxy resin Substances 0.000 claims abstract description 20
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 20
- 229920002635 polyurethane Polymers 0.000 claims abstract description 15
- 239000004814 polyurethane Substances 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 9
- 239000010703 silicon Substances 0.000 claims abstract description 9
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims abstract description 7
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 claims abstract description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229920005862 polyol Polymers 0.000 claims description 19
- 150000003077 polyols Chemical class 0.000 claims description 19
- 238000003756 stirring Methods 0.000 claims description 16
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 12
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 8
- 239000004593 Epoxy Substances 0.000 claims description 7
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 7
- KSCAZPYHLGGNPZ-UHFFFAOYSA-N 3-chloropropyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCCl KSCAZPYHLGGNPZ-UHFFFAOYSA-N 0.000 claims description 6
- YSWBFLWKAIRHEI-UHFFFAOYSA-N 4,5-dimethyl-1h-imidazole Chemical compound CC=1N=CNC=1C YSWBFLWKAIRHEI-UHFFFAOYSA-N 0.000 claims description 6
- 229920006335 epoxy glue Polymers 0.000 claims description 6
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 6
- 229960004889 salicylic acid Drugs 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- -1 3-cyclohexyldimethylamine Propylene oxide Chemical compound 0.000 claims 1
- GEQHKFFSPGPGLN-UHFFFAOYSA-N cyclohexane-1,3-diamine Chemical compound NC1CCCC(N)C1 GEQHKFFSPGPGLN-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 2
- 239000004843 novolac epoxy resin Substances 0.000 description 2
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
- 241000208829 Sambucus Species 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 235000008995 european elder Nutrition 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
Landscapes
- Adhesives Or Adhesive Processes (AREA)
- Epoxy Resins (AREA)
Abstract
The invention relates to a flexible epoxy adhesive and a preparation method thereof, wherein the flexible epoxy adhesive comprises a component A and a component B; the formula of the component A comprises the following components in parts by mass: 90-100 parts of TDI, 430-640 parts of polyether, 4000-5000 parts of epoxy resin and 40-100 parts of organic silicon; the formula of the component B is as follows: 80-100 parts of 1, 3-cyclohexyldimethylamine, 140-170 parts of epoxypropane butyl ether and 4-10 parts of catalyst. According to the invention, the organosilicon and polyurethane modified epoxy resin are adopted, so that the flexibility is increased, the impact resistance and the stripping resistance are improved, and the epoxy resin is ensured not to be crystallized at 0 ℃. The temperature resistance and the elongation at break of the cured product are greatly improved.
Description
Technical Field
The invention relates to an epoxy adhesive and a preparation method thereof, in particular to a flexible epoxy adhesive and a preparation method thereof.
Background
At present, in the market at home and abroad, in the aspect of improving the temperature resistance of the epoxy adhesive, four-functional group epoxy resin or novolac epoxy resin and polysulfone compounds are mostly adopted to be matched for use. The flexibility of the epoxy cured material is increased by adopting single rubber or polyurethane. The four-functional group epoxy resin has good temperature resistance, and has large activity and short storage period due to the amino group. The temperature resistance of the novolac epoxy resin is improved to a limited extent and is about 120 ℃. Most of the high-temperature-resistant glue on the market needs to be heated and cured, and the operation is complicated.
The unmodified epoxy adhesive has the advantages that a cured product is generally brittle and has poor stripping resistance, impact resistance and cracking resistance. The temperature range of use is limited, typically from 0 ℃ to 100 ℃. When the temperature is lower than 0 ℃, the epoxy resin is crystallized, the use operation is influenced, and when the temperature is higher than 100 ℃, the performance of the epoxy condensate is obviously reduced, and the epoxy condensate cannot be in a high-temperature working environment for a long time.
Disclosure of Invention
The invention aims to provide a flexible epoxy adhesive which comprises a component A and a component B, wherein the component A comprises the following formula in parts by mass:
the formula of the component A is as follows:
the formula of the component B is as follows:
80-110 parts of 1, 3-cyclohexyldimethylamine
140-170 parts of epoxypropane butyl ether
4-10 parts of a catalyst.
Preferably, the component A comprises the following formula in parts by mass:
the formula of the component B is as follows:
the mass ratio of the component A to the component B in the flexible epoxy adhesive is 1.5-2.5: 1, and preferably 2: 1.
The invention further provides that the polyether polyol is selected from at least one of polyether polyol 3050, polyether polyol 3010 and polyether polyol 2070;
wherein 3050, 3010, 2070 represent the functionality and the size of the molecular weight.
Wherein, when the polyether polyol is polyether 3050 and polyether 3010, the effect is best.
The invention further provides that the epoxy resin is selected from at least one of bisphenol A resin E51 and bisphenol A resin E44.
Wherein E51 and E44 conventionally represent epoxy values.
The organic silicon has high activity, particles are easy to generate during reaction, and the reaction rate and the reaction temperature need to be properly controlled during the preparation process.
The invention further provides that the organic silicon is selected from at least one of gamma-chloropropyltriethoxysilane and N-phenyl-gamma-aminopropyltrimethoxysilane; gamma-chloropropyltriethoxysilane is preferred.
The gamma-chloropropyltriethoxysilane has high thermal stability and high temperature resistance, and can effectively improve the flexibility of a cured product.
The invention further provides that the catalyst is selected from the group consisting of dimethylimidazole, salicylic acid, tris- (dimethylaminomethyl) phenol;
preferably, the catalyst is a mixture of dimethylimidazole and salicylic acid;
more preferably, the catalyst is 1:1 dimethylimidazole and salicylic acid.
The invention provides a preferable scheme, the flexible epoxy glue comprises a component A and a component B, and the component A comprises the following formula in parts by mass:
the formula of the component B is as follows:
or the flexible epoxy glue comprises a component A and a component B, wherein the component A comprises the following formula in parts by mass:
the formula of the component B is as follows:
further provides a preferable scheme, the flexible epoxy glue comprises a component A and a component B, and the component A comprises the following formula in parts by mass:
the formula of the component B is as follows:
another object of the present invention is to provide a method for preparing the above flexible epoxy adhesive, wherein the method for preparing the component a comprises the following steps:
1) mixing polyether polyol and toluene diisocyanate, stirring at the temperature of 70-90 ℃ for 3-5 h at the rotating speed of 150-250 rpm, cooling to 25-35 ℃, and adding organic silicon to prepare modified polyurethane;
2) heating epoxy resin to 70-90 ℃, adding the modified polyurethane prepared in the step 1), maintaining the temperature, stirring at a rotating speed of 150-250 rpm for 3-5 h, and cooling to room temperature to obtain the epoxy resin-modified polyurethane;
the preparation method of the component B comprises the following specific steps: mixing epoxypropane butyl ether and 1, 3-cyclohexyldimethylamine, stirring at the temperature of 70-90 ℃ for 3.5-5.5 h at the rotating speed of 200-300 rpm, adjusting the temperature to 30-50 ℃, adding a catalyst, and uniformly stirring to obtain the catalyst.
The invention further provides a preparation method of the component A, which comprises the following steps:
1) mixing polyether polyol and toluene diisocyanate, stirring at the temperature of 75-85 ℃ at the rotating speed of 180-220 rpm for 3.5-4.5 h, cooling to 28-32 ℃, and adding organic silicon to prepare modified polyurethane;
2) heating epoxy resin to 75-85 ℃, adding the modified polyurethane prepared in the step 1), maintaining the temperature, stirring at the rotating speed of 180-220 rpm for 3.5-4.5 h, and cooling to room temperature to obtain the epoxy resin modified polyurethane;
the preparation method of the component B comprises the following specific steps: mixing epoxypropane butyl ether and 1, 3-cyclohexyldimethylamine, stirring at the temperature of 75-85 ℃ at the rotating speed of 230-270 rpm for 4.2-4.7 h, adjusting the temperature to 35-45 ℃, adding a catalyst, and uniformly stirring to obtain the catalyst.
The invention has at least the following beneficial effects:
1. the invention adopts the organic silicon and polyurethane modified epoxy resin, which not only can increase the flexibility and improve the shock resistance and stripping resistance, but also can ensure that the epoxy resin is not crystallized at 0 ℃ and is a flowing liquid. The temperature resistance of the cured material is improved by at least 40%, and the elongation at break is improved by more than 2 times.
2. The components have synergistic effect, so that the temperature resistance of the component A is improved, and the temperature resistance of the component B is also obviously improved; moreover, the components are compatible with each other, so that the reaction activity is further provided.
Detailed Description
The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
Polyether polyols were obtained from dow chemical and epoxy resins from sambucus group in the following examples.
Example 1
The embodiment provides a flexible epoxy adhesive, which consists of a component A and a component B; the formula of the component A comprises the following components in parts by mass:
the formula of the component B is as follows:
example 2
The embodiment provides a flexible epoxy adhesive, which consists of a component A and a component B; the formula of the component A comprises the following components in parts by mass:
the formula of the component B is as follows:
example 3
The embodiment provides a flexible epoxy adhesive, which consists of a component A and a component B; the formula of the component A comprises the following components in parts by mass:
the formula of the component B is as follows:
example 4
The embodiment provides a flexible epoxy adhesive, which consists of a component A and a component B; the formula of the component A comprises the following components in parts by mass:
the formula of the component B is as follows:
example 5
This example provides a flexible epoxy adhesive differing from example 1 in that the organosilicon gamma-chloropropyltriethoxysilane is replaced with N-phenyl-gamma-aminopropyltrimethoxysilane.
Example 6
The embodiment provides a preparation method of a flexible epoxy adhesive, wherein the preparation method of the component A comprises the following steps:
1) mixing polyether polyol and toluene diisocyanate, stirring at the temperature of 80 ℃ at the rotating speed of 200rpm for 4 hours, cooling to 28-32 ℃, and adding organic silicon to prepare modified polyurethane;
2) heating epoxy resin to 80 ℃, adding the modified polyurethane prepared in the step 1), maintaining the temperature, stirring at the rotating speed of 200rpm for 4 hours, and cooling to room temperature to obtain the modified polyurethane;
the preparation method of the component B comprises the following specific steps: mixing epoxypropane butyl ether and 1, 3-cyclohexyldimethylamine, stirring at the temperature of 80 ℃ and the rotation speed of 250rpm for 4.5h, adjusting the temperature to be below 40 ℃, adding a catalyst, and stirring uniformly to obtain the catalyst.
Comparative example 1
This comparative example provides a flexible epoxy adhesive that differs from example 1 in that toluene diisocyanate and polyether polyol are not added; prepared by the same method as in example 6.
Test example 1
The epoxy adhesives prepared in the examples 1-5 and the comparative example 1 are detected by a GB/T7124 adhesive shear strength determination method and a GB/T2567-:
TABLE 1
Test example 2
The examples 1 to 5, comparative example 1 and the commercially available epoxy resins were stored at 0 ℃ for comparison.
After 60min, the component A of the comparative example 1 and the commercial epoxy resin obviously becomes crystalline, loses the flowability and is inoperable; the epoxy resin provided in examples 1-5 remained as it was.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.
Claims (6)
1. The flexible epoxy adhesive is characterized by comprising a component A and a component B; the formula of the component A comprises the following components in parts by mass:
90-100 parts of toluene diisocyanate
3050215-235 parts of polyether polyol
3010215-235 parts of polyether polyol
Bisphenol A resin E515000 parts
90-110 parts of gamma-chloropropyltriethoxysilane,
the formula of the component B is as follows:
90-100 parts of 1, 3-cyclohexyldimethylamine
110-120 parts of epoxypropane butyl ether
1.5-2.5 parts of dimethyl imidazole
1.5-2.5 parts of salicylic acid.
2. The flexible epoxy adhesive according to claim 1, wherein the mass ratio of the component A to the component B is 1.5-2.5: 1.
3. The flexible epoxy adhesive according to claim 2, wherein the mass ratio of the component A to the component B is 2: 1.
4. The flexible epoxy glue of claim 1, wherein the mass ratio of the dimethyl imidazole to the salicylic acid is 1: 1.
5. The flexible epoxy glue according to claim 1, wherein the component A comprises the following formula in parts by mass:
100 parts of toluene diisocyanate
470 parts of polyether polyol
5000 parts of epoxy resin
Organosilicon 100 parts
The polyether polyol is polyether polyol 3050 and polyether polyol 3010, and the mass ratio of the polyether polyol 3050 to the polyether polyol 3010 is 1: 1; the epoxy resin is bisphenol A resin E51, and the organic silicon is gamma-chloropropyltriethoxysilane;
the formula of the component B is as follows:
100 parts of 1, 3-cyclohexyldimethylamine
Propylene oxide butyl ether 115 parts
2 parts of dimethyl imidazole
And 2 parts of salicylic acid.
6. The preparation method of the flexible epoxy glue of any one of claims 1 to 5, characterized in that the preparation method of the component A comprises the following steps:
1) mixing polyether polyol and toluene diisocyanate, stirring at the temperature of 70-90 ℃ for 3-5 h at the rotating speed of 150-250 rpm, cooling to 25-35 ℃, and adding organic silicon to prepare modified polyurethane;
2) heating epoxy resin to 70-90 ℃, adding the modified polyurethane prepared in the step 1), maintaining the temperature, stirring at a rotating speed of 150-250 rpm for 3-5 h, and cooling to room temperature to obtain the epoxy resin-modified polyurethane;
the preparation method of the component B comprises the following specific steps: mixing an epoxy diluent and 1, 3-cyclohexanediamine, stirring at the temperature of 70-90 ℃ for 3.5-5.5 h at the rotating speed of 200-300 rpm, adjusting the temperature to 30-50 ℃, adding a catalyst, and uniformly stirring to obtain the catalyst.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910149179.XA CN109868104B (en) | 2019-02-28 | 2019-02-28 | Flexible epoxy adhesive and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201910149179.XA CN109868104B (en) | 2019-02-28 | 2019-02-28 | Flexible epoxy adhesive and preparation method thereof |
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| CN109868104A CN109868104A (en) | 2019-06-11 |
| CN109868104B true CN109868104B (en) | 2021-06-29 |
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| CN115011297B (en) * | 2022-07-15 | 2023-01-20 | 北京新风航天装备有限公司 | Adhesive for ceramic material and preparation method thereof |
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|---|---|---|---|---|
| US5139857A (en) * | 1990-12-07 | 1992-08-18 | Corning Incorporated | Composite article composed of rigid components with different coefficients of thermal expansion |
| CN102898611A (en) * | 2012-09-11 | 2013-01-30 | 苏州市胶粘剂厂有限公司 | Preparation method for organic silicon polyurethane adhesive |
| CN104726047A (en) * | 2015-03-31 | 2015-06-24 | 吉林大学 | Room-temperature cured high-temperature-resistant epoxy resin plugging material and preparation method thereof |
| CN104927755A (en) * | 2015-07-14 | 2015-09-23 | 黑龙江省科学院石油化学研究院 | Normal-temperature solidification instant-high-temperature-resistant high-flexibility epoxy adhesive and preparing method thereof |
| CN105255418A (en) * | 2015-11-04 | 2016-01-20 | 无锡嘉联电子材料有限公司 | Preparation method of high-transparency flexible epoxy resin adhesive |
-
2019
- 2019-02-28 CN CN201910149179.XA patent/CN109868104B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5139857A (en) * | 1990-12-07 | 1992-08-18 | Corning Incorporated | Composite article composed of rigid components with different coefficients of thermal expansion |
| CN102898611A (en) * | 2012-09-11 | 2013-01-30 | 苏州市胶粘剂厂有限公司 | Preparation method for organic silicon polyurethane adhesive |
| CN104726047A (en) * | 2015-03-31 | 2015-06-24 | 吉林大学 | Room-temperature cured high-temperature-resistant epoxy resin plugging material and preparation method thereof |
| CN104927755A (en) * | 2015-07-14 | 2015-09-23 | 黑龙江省科学院石油化学研究院 | Normal-temperature solidification instant-high-temperature-resistant high-flexibility epoxy adhesive and preparing method thereof |
| CN105255418A (en) * | 2015-11-04 | 2016-01-20 | 无锡嘉联电子材料有限公司 | Preparation method of high-transparency flexible epoxy resin adhesive |
Non-Patent Citations (1)
| Title |
|---|
| 聚氨酯改性室温固化环氧结构胶粘剂的研究;李祥新等;《粘接》;20061215;第27卷(第06期);全文 * |
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