CN105111691A - Epoxy resin composition with high flexibility and hydrophobicity as well as preparation method of composition - Google Patents
Epoxy resin composition with high flexibility and hydrophobicity as well as preparation method of composition Download PDFInfo
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Abstract
The invention relates to epoxy resin composition with high flexibility and hydrophobicity as well as a preparation method of the composition. The composition comprises components in parts by mass as follows: 20-30 parts of epoxy resin I, 20-30 parts of epoxy resin with high flexibility and hydrophobicity, 2-8 parts of a curing agent, 0.05-0.3 parts of a curing accelerator and 30-55 parts of inorganic filler. An organic silicon material is grafted onto the epoxy resin through chemical reactions, flexibility and water resistance of an epoxy resin curing system are effectively improved, meanwhile, the problem that the compatibility of organic silicon with the epoxy resin is poor is solved, and the cold and hot impact resistance and the wet fastness of the epoxy resin composition can be substantially improved when the epoxy resin is applied to the epoxy resin composition.
Description
Technical field
The invention belongs to electronic package material field, relate to a kind of high-flexibility and hydrophobicity composition epoxy resin and preparation method thereof.
Background technology
Epoxy resin carries out polycondensation and obtained product by having the compound of epoxy group(ing) and multi-hydroxy or polyol compound, it is one of most widely used matrix resin in polymer matrix composite, there is high strength, excellent cohesiveness, chemical resistance, electrical insulation properties, mechanical property, and be easy to processing, shrinking percentage is low, coefficient of linear expansion is little and the advantage such as with low cost, is widely used in the encapsulation of the electronic devices and components such as voltage dependent resistor, ceramic condenser, diode, triode.
But because the toughness of pure epoxy resin is not enough, cause curing material crisp, the defect such as easily to crack, its application receives larger restriction, particularly requiring that cured article has field compared with high-flexibility as the encapsulation field of electronic devices and components.Based on this, Chinese scholars has carried out a large amount of study on the modification work to epoxy resin, summarizes many epoxy resin toughened methods.On the other hand, epoxy resin, as the important film forming matter of electronic package material, along with the continuous lifting of service requirements, requires that epoxy resin has stronger wet fastness.Therefore, for electronic package material field, the research of fragility and wet fastness aspect quietly becomes the important research content of this area.And organosilicon material has the advantages such as excellent wet fastness and low temperature flexibility.Therefore, by introducing flexible silicone segments in epoxy molecule chain, effectively can improve snappiness and the wet fastness of epoxy resin solidifying system, the internal stress of cured article can be reduced simultaneously.
Based on feature and the prior art of above electronic devices and components packaged material, the material with organosilicon structures is introduced in epoxy molecule chain by the method for chemical reaction by the present invention, thus improve snappiness and the wet fastness of epoxy resin solidifying system, solve the problem of common organosilicon material and epoxy resin compatibility difference simultaneously.Then, high-flexibility will be had and hydrophobic epoxy resin is used for composition epoxy resin, and then significantly the cold-hot impact of enhancing ring epoxy resin composition and wet fastness.
Summary of the invention
The object of the invention is to overcome the deficiencies in the prior art part, a kind of high-flexibility and hydrophobicity composition epoxy resin and preparation method thereof be provided, prepared composition epoxy resin technique is simple, administration measure.
The technical scheme that the present invention realizes its object is:
A kind of high-flexibility and hydrophobicity composition epoxy resin, its form component and mass fraction as follows:
The synthetic method of described high-flexibility and hydrophobicity epoxy resin is as follows:
(1) in the four-hole boiling flask that heating jacket, agitator, thermometer, distillation column and prolong are housed, add a certain amount of liquid-state epoxy resin, be warming up to more than 120 DEG C, open vacuum pump (vacuum tightness <-0.08MPa), stir 0.5h, the cut in extracted liquid epoxy resin;
(2) to adding active organosilicon and catalyzer except in the liquid-state epoxy resin of cut, if active organosilicon is liquid, adopt the mode dripped, dropwise in half an hour, then logical nitrogen protection, after it fully mixes, is slowly warming up to 140 ~ 170 DEG C, reaction 1 ~ 3h, is cooled to about 130 DEG C;
(3) add polyphenol and catalyzer, logical nitrogen protection, meanwhile, is adjusted between 140 ~ 170 DEG C by temperature, reaction 1 ~ 2h; Color becomes light yellow clear liquid, stopped reaction.
(4) cooling discharge, after cooling compressing tablet, can obtain high flexibility and hydrophobic epoxy resin, in light yellow clear shape; The epoxy equivalent (weight) scope of this epoxy resin is 500 ~ 1000g/eq, and softening point range is 85 ~ 100 DEG C, and range of viscosities is 800 ~ 2500mPas/150 DEG C.
Wherein, the mass fraction of described each component is:
And described epoxy resin I requires that softening temperature is 60 ~ 110 DEG C, oxirane value is 0.12 ~ 0.25eq/100g.
And described epoxy resin I comprises diglycidyl ether type epoxy resin, glycidyl ester type epoxy resin, preferred bisphenol A type epoxy resin.
And the epoxy equivalent (weight) scope of described high flexibility and hydrophobicity epoxy resin is 500 ~ 1000g/eq, and softening point range is 85 ~ 100 DEG C, and range of viscosities is 800 ~ 2500mPas/150 DEG C.
And, described liquid-state epoxy resin is at least one in following epoxy resin: diglycidyl ether type epoxy resin, glycidyl ester type epoxy resin, glycidyl amine type epoxy resin, cycloaliphatic epoxy resin and wire aliphatic epoxy resin, and oxirane value is not less than 0.5eq/100g; Described active organosilicon is at least one in phenylbenzene two silanol, dimethyl two silanol, end hydroxyalkyl groups polysiloxane compound (hydroxyl equivalent 300-800g/eq, molecular structural formula is shown below); Described polyphenol is at least one in dihydroxyphenyl propane, Bisphenol F, bisphenol S; Described catalyzer is the wherein one of methyltriphenylphospbromide bromide phosphorus, Ethyltriphenylphosphonium brimide, dibutyl tin dilaurate.
End hydroxyalkyl groups polysiloxane compound molecular structural formula
And described solidifying agent is at least one in organic acid or anhydrides.
And described curing catalyst is any one in imidazoles, imidazolines, trialkyl phosphorus, quaternary ammonium salt, quaternary phosphine salt, organic ureas;
And described mineral filler is at least one in silica flour, talcum powder, calcium carbonate, mica powder, wollastonite.
A kind of high-flexibility and hydrophobicity composition epoxy resin and preparation method thereof, is characterized in that: step is as follows:
Epoxy resin I, high-flexibility and hydrophobicity epoxy resin, solidifying agent, curing catalyst and mineral filler are carried out pre-mixing by mass fraction proportioning, and the time of pre-mixing is 5 ~ 20min, rotating speed 500 ~ 1000r/min; Then melting mixing is extruded, wherein extrusion temperature 70 ~ 150 DEG C, forcing machine rotating speed 1500 ~ 3000r/min, rate of feeding 900 ~ 2400r/min, then carries out pulverizing and sieving obtaining described composition epoxy resin.
The present invention has the following advantages:
(1) the present invention makes the synthesis technique of high-flexibility and hydrophobicity epoxy resin by oneself simply, administration measure.
(2) the present invention makes high-flexibility and hydrophobicity epoxy resin by oneself, adopts mass polymerization, and in building-up process, non-volatile part generates, and the feature of environmental protection is strong.
(3) organosilicon material is grafted on epoxy resin by chemical reaction by the present invention, effectively improve snappiness and the water tolerance of epoxy resin solidifying system, solve the problem of organosilicon and epoxy resin compatibility difference simultaneously, for composition epoxy resin, the wet fastness of the cold-hot impact of composition epoxy resin can be increased substantially.
Embodiment
Below in conjunction with specific embodiment, the invention will be further described, and following examples are descriptive, is not determinate, can not limit protection scope of the present invention with this.
Embodiment 1
A kind of high-flexibility and hydrophobicity composition epoxy resin, its preparation method is as follows:
Epoxy resin I, high-flexibility and hydrophobicity epoxy resin A, solidifying agent, curing catalyst and mineral filler are carried out pre-mixing by mass fraction proportioning, and the time of pre-mixing is 5 ~ 20min, rotating speed 500 ~ 1000r/min; Then melting mixing is extruded (extrusion temperature 70 ~ 150 DEG C, forcing machine rotating speed 1500 ~ 3000r/min, rate of feeding 900 ~ 2400r/min), then carries out pulverizing and sieving obtaining described composition epoxy resin.
Wherein, the synthetic method of a kind of high-flexibility and hydrophobicity epoxy resin (A), step is as follows:
(1) in the 1L four-hole boiling flask that heating jacket, agitator, thermometer, distillation column and prolong are housed, add 650g127E, be warming up to 120 DEG C, open vacuum pump, stir 0.5 hour, close vacuum pump;
(2) then drip 8.89g and hold hydroxyalkyl groups polysiloxane compound, dropwise in half an hour, add 35.47g phenylbenzene two silanol and 2.08g dibutyl tin dilaurate afterwards, be warming up to 130 DEG C, after logical nitrogen mixes, be warming up to 140 ~ 170 DEG C, reaction 1 ~ 3h, is cooled to about 130 DEG C;
(3) add 190.3g dihydroxyphenyl propane and 0.57g dibutyl tin dilaurate, temperature is adjusted to 140 ~ 170 DEG C simultaneously, and nitrogen protection, after reaction 1 ~ 2h, stopped reaction;
(4) cooling discharge, through cooling compressing tablet, can obtain light yellow clear shape epoxy resin A.The equivalent of this epoxy resin is 630g/eq, and melt viscosity is 13mPas/180 DEG C, and softening temperature is 87 DEG C.
Embodiment 2
A kind of high-flexibility and hydrophobicity composition epoxy resin, its preparation method is as follows:
Epoxy resin I, high-flexibility and hydrophobicity epoxy resin B, solidifying agent, curing catalyst and mineral filler are carried out pre-mixing by mass fraction proportioning, and the time of pre-mixing is 5 ~ 20min, rotating speed 500 ~ 1000r/min; Then melting mixing is extruded (extrusion temperature 70 ~ 150 DEG C, forcing machine rotating speed 1500 ~ 3000r/min, rate of feeding 900 ~ 2400r/min), then carries out pulverizing and sieving obtaining described composition epoxy resin.
Wherein, the synthetic method of a kind of high-flexibility and hydrophobicity epoxy resin (B), step is as follows:
(1) in the 1L four-hole boiling flask that heating jacket, agitator, thermometer, distillation column and prolong are housed, add 630g127E, be warming up to 120 DEG C, open vacuum pump, stir 0.5 hour, close vacuum pump;
(2) then drip 12.77g and hold hydroxyalkyl groups polysiloxane compound, dropwise in half an hour, add 50.85g phenylbenzene two silanol and 2.08g dibutyl tin dilaurate afterwards, be warming up to 130 DEG C, after logical nitrogen mixes, be warming up to 140 ~ 170 DEG C, reaction 1 ~ 3h, is cooled to about 130 DEG C;
(3) add 184.5g dihydroxyphenyl propane and 0.55g dibutyl tin dilaurate, temperature is adjusted to 140 ~ 170 DEG C simultaneously, and nitrogen protection, after reaction 1 ~ 2h, stopped reaction;
(4) cooling discharge, through cooling compressing tablet, can obtain light yellow clear shape epoxy resin B.The equivalent of this epoxy resin is 730g/eq, and melt viscosity is 17mPas/180 DEG C, and softening temperature is 89 DEG C.
Comparative example:
Epoxy resin I, solidifying agent, curing catalyst, mineral filler are carried out pre-mixing by mass fraction proportioning, and the time of pre-mixing is 5 ~ 20min, rotating speed 500 ~ 1000r/min; Then melting mixing is extruded (extrusion temperature 70 ~ 150 DEG C, forcing machine rotating speed 1500 ~ 3000r/min, rate of feeding 900 ~ 2400r/min), then carries out pulverizing and sieving.
The proportioning of three groups of example composition components and the performance of coating curing thing as shown in table 1.
The cold-hot impact of table 1 epoxy composite component proportion and coating curing thing and wet fastness
| Component | Unit | Reference example | Embodiment 1 | Embodiment 2 |
| Epoxy resin I (E-12) | g | 50 | 35 | 35 |
| High-flexibility and hydrophobicity epoxy resin (A) | g | — | 15 | — |
| High-flexibility and hydrophobicity epoxy resin (B) | g | — | — | 15 |
| Solidifying agent: trimellitic acid 1,2-anhydride | g | 7 | 7 | 7 |
| Curing catalyst: imidazoles | g | 0.2 | 0.2 | 0.2 |
| Mineral filler: SiO 2 | g | 50 | 50 | 50 |
| Cold-hot impact | Individual | 20 | 60 | 80 |
| Coating water-intake rate (wet fastness) | ％ | 0.35 | 0.18 | 0.12 |
Form components description as follows:
Involved epoxy resin I is diglycidyl ether type epoxy resin, glycidyl ester type epoxy resin, preferred bisphenol A type epoxy resin; Require that softening temperature is 60 ~ 110 DEG C, oxirane value is 0.12 ~ 0.25eq/100g, account for 20 ~ 30 mass parts of encapsulating material total amount.
The epoxy equivalent (weight) scope of described high flexibility and hydrophobicity epoxy resin is 500 ~ 1000g/eq, and softening point range is 85 ~ 100 DEG C, and range of viscosities is 800 ~ 2500mPas/150 DEG C, accounts for 20 ~ 30 mass parts of encapsulating material total amount.
Designed solidifying agent is at least one in organic acid or anhydrides, accounts for 2 ~ 8 mass parts of encapsulating material total amount.
Involved curing catalyst is any one in imidazoles, imidazolines, trialkyl phosphorus, quaternary ammonium salt, quaternary phosphine salt, organic ureas, accounts for 0.05 ~ 0.3 mass parts of encapsulating material total amount.
Involved mineral filler is at least one in silica flour, talcum powder, calcium carbonate, mica powder, wollastonite.The median size of these mineral fillers is between 1 ~ 50 micron.When median size is less, easily cause resin combination viscosity to rise, cause its packaging process to be deteriorated; And when median size is larger, can cause again resin and filler distribution uneven, thus have influence on its physical and mechanical properties.The addition of this mineral filler accounts for 30 ~ 55 mass parts of composition epoxy resin gross weight.
Wherein, the synthetic method of the high flexibility that the present invention uses and hydrophobicity epoxy resin, step is as follows:
(1) in the four-hole boiling flask that heating jacket, agitator, thermometer, distillation column and prolong are housed, add a certain amount of liquid-state epoxy resin, be warming up to more than 120 DEG C, open vacuum pump (vacuum tightness <-0.08MPa), stir 0.5h, the cut in extracted liquid epoxy resin;
(2) to adding active organosilicon and catalyzer except in the liquid-state epoxy resin of cut, if active organosilicon is liquid, adopt the mode dripped, dropwise in half an hour, then logical nitrogen protection, after it fully mixes, is slowly warming up to 140 ~ 170 DEG C, reaction 1 ~ 3h, is cooled to about 130 DEG C;
(3) add polyphenol and catalyzer, logical nitrogen protection, meanwhile, is adjusted between 140 ~ 170 DEG C by temperature, reaction 1 ~ 2h; Color becomes light yellow clear liquid, stopped reaction.
(4) cooling discharge, after cooling compressing tablet, can obtain high flexibility and hydrophobic epoxy resin, in light yellow clear shape; The epoxy equivalent (weight) scope of this epoxy resin is 500 ~ 1000g/eq, and softening point range is 85 ~ 100 DEG C, and range of viscosities is 800 ~ 2500mPas/150 DEG C.
Wherein, the mass fraction of described each component is:
Described liquid-state epoxy resin is at least one in following epoxy resin: diglycidyl ether type epoxy resin, glycidyl ester type epoxy resin, glycidyl amine type epoxy resin, cycloaliphatic epoxy resin and wire aliphatic epoxy resin, and oxirane value is not less than 0.5eq/100g; Described active organosilicon is at least one in phenylbenzene two silanol, dimethyl two silanol, end hydroxyalkyl groups polysiloxane compound (hydroxyl equivalent 300-1000g/mol, molecular structural formula is shown below); Described polyphenol is at least one in dihydroxyphenyl propane, Bisphenol F, bisphenol S; Described catalyzer is the wherein one of methyltriphenylphospbromide bromide phosphorus, Ethyltriphenylphosphonium brimide, dibutyl tin dilaurate.
The using method of this high flexibility and hydrophobicity composition epoxy resin:
By in 160 ± 10 DEG C of baking ovens the electronic devices and components such as voltage dependent resistor, ceramic condenser of preheating 30min to immerse in previously prepared powder powder (composition epoxy resin provided by the invention), then be put in 160 DEG C ± 10 baking ovens and solidify 1 ~ 2h.
Testing performance index method involved in the present invention is as follows:
(1) the mensuration of epoxy equivalent (weight): according to ISO3001-1978 " mensuration of plastics-epoxy compounds-epoxy equivalent (weight) ";
(2) melt viscosity: use Brookfield cone-and-plate viscometer to measure the melt viscosity of phosphorous-containing polyester solidifying agent at different temperature;
(3) softening temperature: measure according to the method described in GB12007.6-89 " epoxy resin softening point measurement method ring and ball method ";
(4) water-intake rate: measure according to the method described in GB1738-79 " insullac paint film water-intake rate assay method ";
(5) cold-hot impact: be that the destructive test that ftractures is occurred in the environment of high temperature and low temperature successively alternation to the coating of electronic devices and components; The design temperature of high temperature and time length all can require to set according to difference, and low temperature is also like this; The resistance to high temperature of coating and a low temperature, be called a circulation; The cycle index of coating before cracking is more, and its cold-hot impact property is better.
Cold-hot impact condition involved in the present invention: high temperature is set as+125 DEG C, and low temperature is set as-40 DEG C, and a high temperature and a low temperature continuous time are 30min, voltage dependent resistor magnetic sheet used, diameter 20 Φ, often organizes experiment 10 prints.
Claims (10)
1. high-flexibility and a hydrophobicity composition epoxy resin, is characterized in that: its form component and mass fraction as follows:
The content of described epoxy resin I does not comprise high-flexibility and hydrophobicity epoxy resin;
The synthetic method of described high-flexibility and hydrophobicity epoxy resin is as follows:
(1) in flask, add a certain amount of liquid-state epoxy resin, be warming up to more than 120 DEG C, open vacuum pump, stir 0.5h, the cut in extracted liquid epoxy resin;
(2) to adding active organosilicon and catalyzer except in the liquid-state epoxy resin of cut, dropwise in half an hour, then logical nitrogen protection, after it fully mixes, is slowly warming up to 140 ~ 170 DEG C, and reaction 1 ~ 3h, is cooled to about 130 DEG C;
(3) add polyphenol and catalyzer, logical nitrogen protection, meanwhile, is adjusted between 140 ~ 170 DEG C by temperature, reaction 1 ~ 2h; Color becomes light yellow clear liquid, stopped reaction;
(4) cooling discharge, after cooling compressing tablet, namely obtains high flexibility and hydrophobic epoxy resin;
Wherein, the mass fraction of described each component is:
2. high-flexibility according to claim 1 and hydrophobicity composition epoxy resin, is characterized in that: described high flexibility and hydrophobic epoxy resin are light yellow clear shape; The epoxy equivalent (weight) scope of this epoxy resin is 500 ~ 1000g/eq, and softening point range is 85 ~ 100 DEG C, and range of viscosities is 800 ~ 2500mPas/150 DEG C.
3. high-flexibility according to claim 1 and hydrophobicity composition epoxy resin, is characterized in that: described epoxy resin I requires that softening temperature is 60 ~ 110 DEG C, oxirane value is 0.12 ~ 0.25eq/100g.
4. high-flexibility according to claim 1 and hydrophobicity composition epoxy resin, is characterized in that: described epoxy resin I comprises diglycidyl ether type epoxy resin, glycidyl ester type epoxy resin, preferred bisphenol A type epoxy resin.
5. high-flexibility according to claim 1 and hydrophobicity composition epoxy resin, it is characterized in that: described liquid-state epoxy resin is at least one in following epoxy resin: diglycidyl ether type epoxy resin, glycidyl ester type epoxy resin, glycidyl amine type epoxy resin, cycloaliphatic epoxy resin and wire aliphatic epoxy resin, oxirane value is not less than 0.5eq/100g; Described active organosilicon is at least one in phenylbenzene two silanol, dimethyl two silanol, end hydroxyalkyl groups polysiloxane compound; The hydroxyl equivalent of described end hydroxyalkyl groups polysiloxane compound is 300-800g/eq;
Described polyphenol is at least one in dihydroxyphenyl propane, Bisphenol F, bisphenol S;
Described catalyzer is the wherein one of methyltriphenylphospbromide bromide phosphorus, Ethyltriphenylphosphonium brimide, dibutyl tin dilaurate.
6. high-flexibility according to claim 1 and hydrophobicity composition epoxy resin, is characterized in that: described end hydroxyalkyl groups polysiloxane compound molecular structural formula is as follows:
7. high-flexibility according to claim 1 and hydrophobicity composition epoxy resin, is characterized in that: described solidifying agent is at least one in organic acid or anhydrides.
8. high-flexibility according to claim 1 and hydrophobicity composition epoxy resin, is characterized in that: described curing catalyst is any one in imidazoles, imidazolines, trialkyl phosphorus, quaternary ammonium salt, quaternary phosphine salt, organic ureas.
9. high-flexibility according to claim 1 and hydrophobicity composition epoxy resin, is characterized in that: described mineral filler is at least one in silica flour, talcum powder, calcium carbonate, mica powder, wollastonite.
10. a high-flexibility and hydrophobicity composition epoxy resin and preparation method thereof, is characterized in that: step is as follows:
Epoxy resin I, high-flexibility and hydrophobicity epoxy resin, solidifying agent, curing catalyst and mineral filler are carried out pre-mixing by mass fraction proportioning, and the time of pre-mixing is 5 ~ 20min, rotating speed 500 ~ 1000r/min; Then melting mixing is extruded, wherein extrusion temperature 70 ~ 150 DEG C, forcing machine rotating speed 1500 ~ 3000r/min, rate of feeding 900 ~ 2400r/min, then carries out pulverizing and sieving obtaining described composition epoxy resin.
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| CN106366293A (en) * | 2016-08-30 | 2017-02-01 | 天津凯华绝缘材料股份有限公司 | Synthesis method of epoxy resin with high weather fastness and flexibility |
| CN106398460A (en) * | 2016-08-30 | 2017-02-15 | 天津凯华绝缘材料股份有限公司 | High-weather-resistance and high-flexibility epoxy resin composition and preparation method thereof |
| CN106632995A (en) * | 2016-11-17 | 2017-05-10 | 中国人民解放军61489部队 | Modified epoxy resin seepage-prevention and leak-stopping grouting material and method for concrete in arctic-alpine area |
| CN107936890A (en) * | 2017-11-27 | 2018-04-20 | 嘉兴联合化学有限公司 | A kind of epoxy resin adhesive for the oxygen aging of resistance to atom and preparation method thereof |
| CN108467568A (en) * | 2018-02-27 | 2018-08-31 | 榛硕（武汉）智能科技有限公司 | A kind of organosilicon epoxy resin composite material and preparation method |
| CN109385241A (en) * | 2018-10-11 | 2019-02-26 | 中国科学院长春应用化学研究所 | A kind of silicon Graft Epoxy Resin adhesive |
| CN111534259A (en) * | 2020-04-02 | 2020-08-14 | 烟台德邦科技有限公司 | Moisture-resistant low-temperature-curing epoxy adhesive and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106366293A (en) * | 2016-08-30 | 2017-02-01 | 天津凯华绝缘材料股份有限公司 | Synthesis method of epoxy resin with high weather fastness and flexibility |
| CN106398460A (en) * | 2016-08-30 | 2017-02-15 | 天津凯华绝缘材料股份有限公司 | High-weather-resistance and high-flexibility epoxy resin composition and preparation method thereof |
| CN106632995A (en) * | 2016-11-17 | 2017-05-10 | 中国人民解放军61489部队 | Modified epoxy resin seepage-prevention and leak-stopping grouting material and method for concrete in arctic-alpine area |
| CN107936890A (en) * | 2017-11-27 | 2018-04-20 | 嘉兴联合化学有限公司 | A kind of epoxy resin adhesive for the oxygen aging of resistance to atom and preparation method thereof |
| CN107936890B (en) * | 2017-11-27 | 2020-09-29 | 嘉兴联合化学有限公司 | Epoxy resin adhesive resistant to atomic oxygen aging and preparation method thereof |
| CN108467568A (en) * | 2018-02-27 | 2018-08-31 | 榛硕（武汉）智能科技有限公司 | A kind of organosilicon epoxy resin composite material and preparation method |
| CN108467568B (en) * | 2018-02-27 | 2021-03-23 | 榛硕（武汉）智能科技有限公司 | Organic silicon epoxy resin composite material and preparation method thereof |
| CN109385241A (en) * | 2018-10-11 | 2019-02-26 | 中国科学院长春应用化学研究所 | A kind of silicon Graft Epoxy Resin adhesive |
| CN111534259A (en) * | 2020-04-02 | 2020-08-14 | 烟台德邦科技有限公司 | Moisture-resistant low-temperature-curing epoxy adhesive and preparation method thereof |
| CN111534259B (en) * | 2020-04-02 | 2022-05-17 | 烟台德邦科技股份有限公司 | Moisture-resistant low-temperature-curing epoxy adhesive and preparation method thereof |
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