CN107033354A - A kind of liquid cage-type silsesquioxane and preparation method thereof - Google Patents
A kind of liquid cage-type silsesquioxane and preparation method thereof Download PDFInfo
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- CN107033354A CN107033354A CN201710286906.8A CN201710286906A CN107033354A CN 107033354 A CN107033354 A CN 107033354A CN 201710286906 A CN201710286906 A CN 201710286906A CN 107033354 A CN107033354 A CN 107033354A
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- cage
- type silsesquioxane
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- aminoethylaminopropyl
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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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
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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
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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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
Abstract
The invention belongs to fine chemistry industry preparation field, disclose a kind of liquid cage-type silsesquioxane and preparation method thereof, liquid cage-type silsesquioxane is using aminoethylaminopropyl trimethoxy silane as raw material, pass through the aminoethylaminopropyl cage-type silsesquioxane of hydrolytic condensation composite solid state first, afterwards with small molecule N, the cage-type silsesquioxane of liquid is made in the reaction of the expoxy propane of N lignocaines 1,2.The present invention has synthesized aminoethylaminopropyl cage-type silsesquioxane by aminoethylaminopropyl trimethoxy silane, and the cage-type silsesquioxane of liquid is prepared on the basis of aminoethylaminopropyl cage-type silsesquioxane.Obtained liquid cage-type silsesquioxane greatly improves its compatibility and dispersiveness with epoxy resin, facilitate construction technology to be modified the solidified resin that the cage-type silsesquioxane of obtained liquid is used for epoxy resin, improve the hot property and mechanical property of epoxy resin.
Description
Technical field
The invention belongs to fine chemistry industry preparing technical field, more particularly to a kind of liquid cage-type silsesquioxane and its preparation
Method.
Background technology
Cage-type silsesquioxane (POSS) constitutes internal cage modle inorganic skeleton by Si and O, the organic group of external connection
Inorganic/organic Hybrid Materials with nanoscale.Due to inorganic/organic hybrid and the structure with external functional group is special
Levy, POSS can be used cooperatively with a variety of thermosetting resins, form the nanometer reinforced polymeric material of inorganic/organic hybrid.
The heat-resisting epoxy resin kind of high-performance, height, which is mainly those, to be had heat resistance skeleton or can improve crosslink density
Polyfunctional epoxy resin.Except the influence of epoxy resin self structure, the influence of curing agent species is another of its heat resistance
Key factor.In general, they or with stable chemical constitution or with increasing after polyfunctionality, with epoxy resin reaction
Cross linking of epoxy resin degree and stability, so as to improve its heat resistance.Amino cage-type silsesquioxane is that to possess heat resistance excellent
Different silicon cage group, can provide the crosslink density that other curing agent are extremely difficult to, greatly improve the resistance to of epoxy resin again
Heat and mechanical property.
The method of traditional modified epoxy is frequently with thermoplastic resin, rubber elastomer, TLCP, rigidity
Particle, organosilicon etc. are modified to epoxy resin, but these method of modifying, generally while a certain performance is improved, loss is another
Outer performance, such as rubber toughened usual reduction heat resistance.Substantial amounts of research, Frank have been carried out to POSS both at home and abroad for this
J.Feher et al. synthesizes a series of different structure POSS, the system research to POSS synthesis condition.Dong Xihua etc. utilizes ammonia third
Base cage modle siloxanes (OapPOSS) has done study on the modification to epoxy resin adhesive.But the cage model sesquialter silica reported at present
Alkane (POSS) is in solid-like pulverulence more, very poor with epoxy resin compatibility, it is difficult to dispersed.
In summary, the problem of prior art is present be：Prior art is generally while a certain performance is improved, and loss is another
Outer performance, and the product and the compatibility and bad dispersibility of epoxy resin of prior art preparation, the hot property of epoxy resin
And poor mechanical property.
The content of the invention
The problem of existing for prior art, the invention provides a kind of liquid cage-type silsesquioxane and its preparation side
Method.
The present invention is achieved in that a kind of cage-type silsesquioxane of liquid, the cage-type silsesquioxane of the liquid
Structural formula it is as follows：
Another object of the present invention is to provide a kind of liquid cage-type silsesquioxane preparation method, the liquid cage model sesquialter
Siloxanes preparation method passes through the ammonia second of hydrolytic condensation composite solid state first using aminoethylaminopropyl trimethoxy silane as raw material
Base aminopropyl cage type sesquialter siloxane, afterwards with small molecule N, the cage modle of liquid is made in the reaction of N- lignocaines -1,2- expoxy propane
Silsesquioxane；Specifically include following steps：
Step one, deionized water, TBAH, isopropanol are added in round-bottomed flask, stirs and heats up, is added dropwise
Aminoethylaminopropyl trimethoxy silane, heats up after stirring, reaction；White powder is filtrated to get, is dried in vacuo, obtains solid-state
Aminoethylaminopropyl cage-type silsesquioxane；
Step 2, epoxychloropropane and diethylamine are added in flask, deionized water is slowly added dropwise；Reaction, then cools；
Sodium hydroxide wiring solution-forming soluble in water is added in reaction bulb, stirring is further continued for；Organic phase is separated with separatory funnel, through water
Wash, extract, drying process, be made N, N- lignocaine -1,2- expoxy propane；
Step 3, takes N, and N- lignocaine -1,2- expoxy propane is in four-hole boiling flask, heating, by the aminoethyl ammonia of synthesis
Propyl group cage-type silsesquioxane is dissolved in methanol；Then it is slowly dropped under agitation equipped with N, N- lignocaines -1,2-
In the four-hole boiling flask of expoxy propane, back flow reaction；Stop evaporation of solvent after reaction, baking removes residual solvent, obtains yellow sticky
Liquid, is described liquid cage-type silsesquioxane.
Further, step one is specifically included：10g deionized waters, 0.21g tetrabutylammonium hydroxides are added in round-bottomed flask
Ammonium, 31g isopropanols, stir and are warming up to 30 DEG C, are slowly added dropwise after 40.25g aminoethylaminopropyl trimethoxy silanes, stirring 5h
78 DEG C are warming up to, 19h is reacted.White powder is filtrated to get, 24h is dried in vacuo, the aminoethylaminopropyl cage modle times of solid-state is obtained
Half siloxanes.
Further, step 2 is specifically included：37g epoxychloropropane and 28.8g diethylamine are added in flask, is slowly added dropwise
12g deionized waters, react 6h at 29 DEG C, then cool to 22 DEG C, 16g sodium hydroxides are dissolved in into wiring solution-forming in 30.4ml water adds
Enter into reaction bulb, be further continued for stirring 40min；Organic phase is separated with separatory funnel, through washing, extraction, 80 DEG C of vacuum drying 24h
Processing, is made N, N- lignocaine -1,2- expoxy propane.
Further, step 3 is specifically included：5.08gN is taken, N- lignocaine -1,2- expoxy propane rises in four-hole boiling flask
The 1.76g aminoethylaminopropyl cage-type silsesquioxanes of synthesis are dissolved in 25.28g methanol, then in stirring bar by temperature to 70 DEG C
It is slowly dropped under part equipped with N, in the four-hole boiling flask of N- lignocaine -1,2- expoxy propane, 70 DEG C of back flow reaction 4h；Stop anti-
Evaporation of solvent after answering, removes residual solvent in 80 DEG C of bakings, obtains yellow thick liquid, is described liquid cage model sesquialter silica
Alkane.
Further, the liquid cage-type silsesquioxane chemical molecular formula synthetic route is specially：
Another object of the present invention is to provide a kind of rubber prepared using above-mentioned liquid cage-type silsesquioxane.
Advantages of the present invention and good effect are：Liquid cage-type silsesquioxane crosslinking agent prepared by the present invention has fine
Compatibility and dispersiveness, by adding UV-curable epoxy temperature tolerance, high rigidity made from cage-type silsesquioxane
The characteristics of, high temperature resistant temperature reaches more than 260 DEG C.
Sample prepared by the present invention is analyzed after tested, and temperature during its thermal weight loss 5% is 380 DEG C, and glass transition temperature is 141
DEG C, tensile strength is 60MPa, and break-draw rate is 80%, and toughness is 1127Pa.
The present invention has synthesized aminoethylaminopropyl cage-type silsesquioxane by aminoethylaminopropyl trimethoxy silane, is
Improve the compatibility and dispersiveness of aminoethylaminopropyl cage-type silsesquioxane and epoxy resin, in aminoethylaminopropyl cage modle times
The cage-type silsesquioxane of liquid is prepared on the basis of half siloxanes.The cage-type silsesquioxane of obtained liquid is used for ring
The solidified resin of oxygen tree fat is modified, and improves the hot property and mechanical property of epoxy resin.
Brief description of the drawings
Fig. 1 is liquid cage-type silsesquioxane preparation method flow chart provided in an embodiment of the present invention.
Embodiment
In order to make the purpose , technical scheme and advantage of the present invention be clearer, with reference to embodiments, to the present invention
It is further elaborated.It should be appreciated that the specific embodiments described herein are merely illustrative of the present invention, it is not used to
Limit the present invention.
The application principle of the present invention is described in detail below in conjunction with the accompanying drawings.
As shown in figure 1, liquid cage-type silsesquioxane preparation method provided in an embodiment of the present invention, is specifically included：
S101:Deionized water, TBAH, isopropanol are added in round-bottomed flask, stirs and is warming up to 30 DEG C,
78 DEG C are warming up to after aminoethylaminopropyl trimethoxy silane, stirring 5h is slowly added dropwise, 19h is reacted.It is filtrated to get white powder,
24h is dried in vacuo, the aminoethylaminopropyl cage-type silsesquioxane of solid-state is obtained.
S102:Epoxychloropropane and diethylamine are added in flask, deionized water is slowly added dropwise, 6h is reacted at 29 DEG C, so
After cool to 22 DEG C, sodium hydroxide wiring solution-forming soluble in water is added in reaction bulb, be further continued for stir 40min.With a point liquid
Funnel separates organic phase, and through the post processing such as washing, extraction, dry, N, N- lignocaine -1,2- expoxy propane is made.
S103:N is taken, N- lignocaine -1,2- expoxy propane is warming up to 70 DEG C in four-hole boiling flask, by the ammonia second of synthesis
Base aminopropyl cage type sesquialter siloxane is dissolved in methanol, is then slowly dropped under agitation equipped with N, and N- lignocaines-
In the four-hole boiling flask of 1,2- expoxy propane, 70 DEG C of back flow reaction 4h.Stop evaporation of solvent after reaction, residue is gone in 80 DEG C of bakings
Solvent, obtains yellow thick liquid, is described liquid cage-type silsesquioxane.
Further, liquid cage-type silsesquioxane preparation method provided in an embodiment of the present invention, with aminoethylaminopropyl three
Methoxy silane is raw material, first by the aminoethylaminopropyl cage-type silsesquioxane of hydrolytic condensation composite solid state, afterwards with it is small
The cage-type silsesquioxane of liquid is made in molecule N, N- lignocaine -1,2 epoxy prapane reaction.Liquid cage-type silsesquioxane
Chemical molecular formula synthetic route is as follows：
The present invention has synthesized aminoethylaminopropyl cage-type silsesquioxane by aminoethylaminopropyl trimethoxy silane, is
Improve the compatibility and dispersiveness of aminoethylaminopropyl cage-type silsesquioxane and epoxy resin, in aminoethylaminopropyl cage modle times
The cage-type silsesquioxane of liquid is prepared on the basis of half siloxanes.The cage-type silsesquioxane of obtained liquid is used for ring
The solidified resin of oxygen tree fat is modified, and improves the hot property and mechanical property of epoxy resin.
The application principle of the present invention is further described with reference to specific embodiment.
Embodiment one：
(1) 10g deionized waters, 0.21g TBAHs, 31g isopropanols are added in 500ml round-bottomed flasks, is stirred
Mix and be warming up to 30 DEG C, 78 DEG C, reaction are warming up to after 40.25g aminoethylaminopropyl trimethoxy silanes, stirring 5h is slowly added dropwise
19h.White powder is filtrated to get, 24h is dried in vacuo, obtains the aminoethylaminopropyl cage-type silsesquioxane of solid-state.
(2) 18.5g epoxychloropropane and 14.4 diethylamine are added in 250ml round-bottomed flasks, 6g deionizations are slowly added dropwise
Water, reacts 6h at 29 DEG C, then cools to 22 DEG C, 8g sodium hydroxides are dissolved in into wiring solution-forming in 15.2ml water is added to reaction bulb
In, it is further continued for stirring 40min.Organic phase is separated with separatory funnel, through the post processing such as washing, extraction, dry, N, N- diethyls is made
Amino -1,2 epoxy prapane.
(3) 2.54gN is taken, N- lignocaine -1,2- expoxy propane is warming up to 70 DEG C in four-hole boiling flask, by synthesis
0.88g aminoethylaminopropyl cage-type silsesquioxanes are dissolved in 12.64g methanol, and dress is then slowly dropped under agitation
Have in N, the four-hole boiling flask of N- lignocaine -1,2- expoxy propane, 70 DEG C of back flow reaction 4h.Stop evaporation removing after reaction molten
Agent, removes residual solvent in 80 DEG C of bakings, obtains yellow thick liquid, is told liquid cage-type silsesquioxane.
By the liquid cage-type silsesquioxane of synthesis by epoxy resin E-51 mass 3% add, and with epoxy resin E-
51 are well mixed, and in 70 DEG C of pre-reaction 30min, then cool to room temperature.Add 5wt% light trigger diphenyl-(4- phenyl
Sulphur) phenyl sulfonium hexafluoro antimonate, irradiates 40s, resin is fully cured after being well mixed under uviol lamp.
Embodiment two：
(1) 10g deionized waters, 0.21g TBAHs, 31g isopropanols are added in 500ml round-bottomed flasks, is stirred
Mix and be warming up to 30 DEG C, 78 DEG C, reaction are warming up to after 40.25g aminoethylaminopropyl trimethoxy silanes, stirring 5h is slowly added dropwise
19h.White powder is filtrated to get, 24h is dried in vacuo, obtains the aminoethylaminopropyl cage-type silsesquioxane of solid-state.
(2) 18.5g epoxychloropropane and 14.4 diethylamine are added in 250ml round-bottomed flasks, 6g deionizations are slowly added dropwise
Water, reacts 6h at 29 DEG C, then cools to 22 DEG C, 8g sodium hydroxides are dissolved in into wiring solution-forming in 15.2ml water is added to reaction bulb
In, it is further continued for stirring 40min.Organic phase is separated with separatory funnel, through the post processing such as washing, extraction, dry, N, N- diethyls is made
Amino -1,2 epoxy prapane.
(3) 2.54gN is taken, N- lignocaine -1,2- expoxy propane is warming up to 70 DEG C in four-hole boiling flask, by synthesis
0.88g aminoethylaminopropyl cage-type silsesquioxanes are dissolved in 12.64g methanol, and dress is then slowly dropped under agitation
Have in N, the four-hole boiling flask of N- lignocaine -1,2- expoxy propane, 70 DEG C of back flow reaction 4h.Stop evaporation removing after reaction molten
Agent, removes residual solvent in 80 DEG C of bakings, obtains yellow thick liquid, is told liquid cage-type silsesquioxane.
By the liquid cage-type silsesquioxane of synthesis by epoxy resin E-51 mass 5% add, and with epoxy resin E-
51 are well mixed, and in 70 DEG C of pre-reaction 30min, then cool to room temperature.Add 5wt% light trigger diphenyl-(4- phenyl
Sulphur) phenyl sulfonium hexafluoro antimonate, irradiates 40s, resin is fully cured after being well mixed under uviol lamp.
Embodiment three：
(1) 10g deionized waters, 0.21g TBAHs, 31g isopropanols are added in 500ml round-bottomed flasks, is stirred
Mix and be warming up to 30 DEG C, 78 DEG C, reaction are warming up to after 40.25g aminoethylaminopropyl trimethoxy silanes, stirring 5h is slowly added dropwise
19h.White powder is filtrated to get, 24h is dried in vacuo, obtains the aminoethylaminopropyl cage-type silsesquioxane of solid-state.
(2) 18.5g epoxychloropropane and 14.4 diethylamine are added in 250ml round-bottomed flasks, 6g deionizations are slowly added dropwise
Water, reacts 6h at 29 DEG C, then cools to 22 DEG C, 8g sodium hydroxides are dissolved in into wiring solution-forming in 15.2ml water is added to reaction bulb
In, it is further continued for stirring 40min.Organic phase is separated with separatory funnel, through the post processing such as washing, extraction, dry, N, N- diethyls is made
Amino -1,2 epoxy prapane.
(3) 2.54gN is taken, N- lignocaine -1,2- expoxy propane is warming up to 70 DEG C in four-hole boiling flask, by synthesis
0.88g aminoethylaminopropyl cage-type silsesquioxanes are dissolved in 12.64g methanol, and dress is then slowly dropped under agitation
Have in N, the four-hole boiling flask of N- lignocaine -1,2- expoxy propane, 70 DEG C of back flow reaction 4h.Stop evaporation removing after reaction molten
Agent, removes residual solvent in 80 DEG C of bakings, obtains yellow thick liquid, is told liquid cage-type silsesquioxane.
By the liquid cage-type silsesquioxane of synthesis by epoxy resin E-51 mass 8% add, and with epoxy resin E-
51 are well mixed, and in 70 DEG C of pre-reaction 30min, then cool to room temperature.Add 5wt% light trigger diphenyl-(4- phenyl
Sulphur) phenyl sulfonium hexafluoro antimonate, irradiates 40s, resin is fully cured after being well mixed under uviol lamp.
The mechanical property of liquid cage-type silsesquioxane modified epoxy
| Component | E-51 epoxy resin | Embodiment one | Embodiment two | Embodiment three |
| Tensile strength (MPa) | 55 | 60 | 70 | 78 |
| Toughness (Pa) | 1024 | 1125 | 1127 | 1196 |
The hot property of liquid cage-type silsesquioxane modified epoxy
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all essences in the present invention
Any modifications, equivalent substitutions and improvements made within refreshing and principle etc., should be included in the scope of the protection.
Claims (7)
1. a kind of cage-type silsesquioxane of liquid, it is characterised in that the structural formula of the cage-type silsesquioxane of the liquid is such as
Under：
2. a kind of liquid cage-type silsesquioxane preparation method as claimed in claim 1, it is characterised in that the liquid cage modle times
Half siloxanes preparation method passes through the ammonia of hydrolytic condensation composite solid state first using aminoethylaminopropyl trimethoxy silane as raw material
Ethylaminopropyl cage-type silsesquioxane, afterwards with small molecule N, the cage of liquid is made in the reaction of N- lignocaines -1,2- expoxy propane
Type silsesquioxane；Specifically include following steps：
Step one, deionized water, TBAH, isopropanol are added in round-bottomed flask, stirs and heats up, ammonia second is added dropwise
Base aminopropyl trimethoxysilane, heats up after stirring, reaction；White powder is filtrated to get, is dried in vacuo, obtains the ammonia second of solid-state
Base aminopropyl cage type sesquialter siloxane；
Step 2, epoxychloropropane and diethylamine are added in flask, deionized water is slowly added dropwise；Reaction, then cools；By hydrogen
Sodium oxide molybdena wiring solution-forming soluble in water is added in reaction bulb, is further continued for stirring；Organic phase is separated with separatory funnel, through washing,
Extraction, drying process, are made N, N- lignocaine -1,2- expoxy propane；
Step 3, takes N, and N- lignocaine -1,2- expoxy propane is in four-hole boiling flask, heating, by the aminoethylaminopropyl of synthesis
Cage-type silsesquioxane is dissolved in methanol；Then it is slowly dropped under agitation equipped with N, N- lignocaine -1,2- epoxies
In the four-hole boiling flask of propane, back flow reaction；Stop evaporation of solvent after reaction, baking removes residual solvent, obtains yellow thick liquid,
As described liquid cage-type silsesquioxane.
3. liquid cage-type silsesquioxane preparation method as claimed in claim 2, it is characterised in that step one is specifically included：
Deionized water, TBAH, isopropanol are added in round-bottomed flask, three's mass ratio is 8-15:0.18-0.24:25-
35, stir and be warming up to 30 DEG C, 78 are warming up to after aminoethylaminopropyl trimethoxy silane 40.25g, stirring 5h is slowly added dropwise
DEG C, react 19h；White powder is filtrated to get, 24h is dried in vacuo, obtains the aminoethylaminopropyl cage-type silsesquioxane of solid-state.
4. liquid cage-type silsesquioxane preparation method as claimed in claim 2, it is characterised in that step 2 is specifically included：
37g epoxychloropropane and 28.8g diethylamine are added in flask, 12g deionized waters are slowly added dropwise, 6h is reacted at 29 DEG C, then
22 DEG C are cooled to, 16g sodium hydroxides are dissolved in into wiring solution-forming in 30.4ml water is added in reaction bulb, be further continued for stirring 40min；
Organic phase is separated with separatory funnel, through washing, extraction, 80 DEG C of vacuum drying 24h processing, N, N- lignocaine -1,2- rings is made
Ethylene Oxide.
5. liquid cage-type silsesquioxane preparation method as claimed in claim 2, it is characterised in that step 3 is specifically included：
5.08gN is taken, N- lignocaine -1,2- expoxy propane is warming up to 70 DEG C in four-hole boiling flask, by the 1.76g aminoethyl ammonia of synthesis
Propyl group cage-type silsesquioxane is dissolved in 25.28g methanol, is then slowly dropped under agitation equipped with N, N- diethylaminos
In the four-hole boiling flask of base -1,2- expoxy propane, 70 DEG C of back flow reaction 4h；Stop evaporation of solvent after reaction, gone in 80 DEG C of bakings
Residual solvent, obtains yellow thick liquid, is described liquid cage-type silsesquioxane.
6. liquid cage-type silsesquioxane preparation method as claimed in claim 2, it is characterised in that the liquid cage model sesquialter
Siloxanes chemical molecular formula synthetic route is specially：
7. rubber prepared by the liquid cage-type silsesquioxane described in a kind of utilization claim 1.
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| CN107698740A (en) * | 2017-11-02 | 2018-02-16 | 合众（佛山）化工有限公司 | A kind of low form epoxy hardener and its epoxide terrace paint based on POSS |
| CN109456486A (en) * | 2018-11-02 | 2019-03-12 | 东华大学 | A kind of multi-functional high temperature resistant POSS nano molecular material and preparation method thereof |
| CN110746606A (en) * | 2019-11-14 | 2020-02-04 | 北京林业大学 | Preparation method of cage-like silsesquioxane cross-linking agent containing epoxy group |
| CN114181655A (en) * | 2021-12-02 | 2022-03-15 | 深圳斯多福新材料科技有限公司 | Environment-friendly MS glue without stannate and preparation method thereof |
| CN114381091A (en) * | 2022-01-14 | 2022-04-22 | 滁州杰事杰新材料有限公司 | Epoxy resin composite material with excellent magnetic property and preparation method thereof |
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| CN114181655A (en) * | 2021-12-02 | 2022-03-15 | 深圳斯多福新材料科技有限公司 | Environment-friendly MS glue without stannate and preparation method thereof |
| CN114381091A (en) * | 2022-01-14 | 2022-04-22 | 滁州杰事杰新材料有限公司 | Epoxy resin composite material with excellent magnetic property and preparation method thereof |
| CN114381091B (en) * | 2022-01-14 | 2023-06-16 | 滁州杰事杰新材料有限公司 | Epoxy resin composite material with excellent magnetic performance and preparation method thereof |
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Application publication date: 20170811 |