CN106519567A - Method for preparing shape-memory epoxy resin particles - Google Patents
Method for preparing shape-memory epoxy resin particles Download PDFInfo
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- CN106519567A CN106519567A CN201610901196.0A CN201610901196A CN106519567A CN 106519567 A CN106519567 A CN 106519567A CN 201610901196 A CN201610901196 A CN 201610901196A CN 106519567 A CN106519567 A CN 106519567A
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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
- C08L95/00—Compositions of bituminous materials, e.g. asphalt, tar, pitch
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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
- C08L2201/12—Shape memory
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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
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Civil Engineering (AREA)
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- Structural Engineering (AREA)
- Epoxy Resins (AREA)
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Abstract
The invention discloses shape-memory epoxy resin particles used for bituminous pavement and production method thereof. The method comprises the following steps: weighing hydrogenated epoxy resin, a flexibilizer and a curing agent according to the ratio of AL-3040 to PPGDGE to IPDA of (4-19): 1: 0.5, weighing 8-12% of an emulsifier, mutually dissolving AL-3040 and PPGDGE, reacting with stirring at the temperature of 50-70 DEG C for 60-180 s to obtain an oil phase; dissolving the emulsifier in distilled water, stirring the materials at the temperature of 50-70 DEG C and reacting the materials for 30-90 s to obtain a water phase; mutually dissolving the water phase and the oil phase, emulsifying the materials at the temperature of 50-70 DEG C for 60-150 s to obtain an oil-in-water emulsion; dissolving IPDA in distilled water, stirring the materials at the temperature of 30-60 DEG C for 30-90 s to obtain an IPDA aqueous solution; dropping the IPDA aqueous solution in the oil-in-water emulsion, stirring the materials at the temperature of 50-70 DEG C for 1-4 h, and filtering moisture to obtain the shape-memory epoxy resin particles. The result shows that the preparation speed is fast, the reaction condition is mild, the purity requirement of a reaction monomer is low, asphalt is doped in the shape-memory epoxy resin particles, so that the elasticity recovery performance of the asphalt can be effectively improved.
Description
Technical field：
The invention belongs to polymer particulate material preparing technical field, and in particular to a kind of shape memory epoxy resin particle
Preparation method.
Background technology：
Asphalt is a kind of typical responsive to temperature type material, and high temperature rut, cold cracking etc. draw because of environment temperature
The disease for rising always perplexs the subject matter of domestic and international road engineering circle.The appearance of rut seriously reduces surface layer and road surface knot
The bulk strength of structure, rainy day Pavement surface drainage be not smooth, or even as rut ponding causes vehicle drift to be slided, affects the safety of high speed traveling
Property；Cracks of Bituminous Pavement at Low-temperature can cause pavement structure depression of bearing force, cause road surface that check crack and pit occur, have a strong impact on car
Ride quality, hence it is evident that shorten the service life on road surface.
For can effectively solve the problem that the diseases such as the high temperature rut and cold cracking of bituminous paving, Chinese scholars are mixed for pitch
The high-temperature stability and cold cracking for closing material has carried out numerous studies.Studies in China worker has carried out wheel tracking test, creep examination
Test, circular track test and loading accelerated test etc., it is proposed that road asphalt pavement performance Study on Climate Division, have studied the car of bituminous paving
Rut prediction model, establishes the prediction model and pavement structure behavior equation of pavement temperature field；Foreign study worker have studied
Asphalt material weather is classified, and as representative, has carried out the list of ground surface material with U.S. AASHTO " mechanics Experience Design guide "
The experimental study high temperature rut such as axle, three axles, shearing, static load, dynamic load, reloading.At the same time, domestic and international researcher to by
The research that cold cracking problem is launched is mainly crack resistance at low-temperature evaluation, compound cryogenic property to be improved and cold performance test
Method is in terms of these three.Although these research contents serve certain positive role, but high temperature rut, the low temperature of bituminous paving
The disease still generally existing such as cracking, always numerous research workers endeavour the direction of exploratory development.
The content of the invention：
It is an object of the invention to provide a kind of preparation method of shape memory epoxy resin particle, the shape memory epoxy
Resin particle is capable of the stimulation of sense temperature, and responds this change, and its mechanics parameter is adjusted, pre- so as to be returned to which
The state for first setting.Shape memory epoxy resin particle is applied in asphalt, when bituminous paving temperature is higher than its glass
During glass transition temperature, particle is in rubbery state, after vehicular load disappears, band when which is returned to reset condition by pressured state
Gathering materials around dynamic, so that slow down the accumulation of deformation.The transfer of shapes temperature of shape memory epoxy resin particle is not high, and can
Transition temperature is adjusted by changing its chemical analysis and the degree of cross linking.Bituminous paving with different temperatures can be chosen properly
Shape memory epoxy resin particle.Its reaction speed in preparation process is fast, mild condition, it is less demanding to monomer purity and
Stable reaction is irreversible.
For reaching above-mentioned purpose, the present invention is adopted the following technical scheme that：
A kind of preparation method of shape memory epoxy resin particle, comprises the following steps：
1) by mol ratio be (4～19):1 hydrogenated epoxy resin is dissolved each other with toughener, the stirring reaction at 50～70 DEG C
60～180s, emulsifying agent is dissolved in distilled water, 30～90s of stirring reaction at 50～70 DEG C, wherein, hydrogenated epoxy resin with
The dissolve each other liquid that obtains of toughener is oil phase, and the liquid that emulsifying agent is obtained in being dissolved in distilled water is water phase；
2) water phase and oil phase are dissolved each other, in 50～70 DEG C of emulsified 60～150s, stable oil-in-water emulsion is obtained；
3) curing agent is dissolved in distilled water, stirs 30～90s at 30～60 DEG C, aqueous solution of curing agent is obtained；
4) by step 3) obtained in aqueous solution of curing agent dropwise instill step 2) obtained in oil-in-water emulsion, 50～
1～4h is stirred at 70 DEG C, is obtained the epoxy particles being molded, is then filtered moisture, obtain shape memory epoxy resin particle.
The present invention is further improved by, step 1) in, hydrogenated epoxy resin is weathe resistance epoxy resin, and the trade mark is
AL-3040, toughener are polypropylene glycol diglycidyl ether, and abbreviation PPGDGE, its molecular weight are 2500, and emulsifying agent is Arab
Gum powder.
The present invention is further improved by, step 2) in the emulsifying agent quality mutually added of water be hydrogenated epoxy resin and increasing
The 8%～12% of tough dose of gross mass.
The present invention be further improved by, step 3) in curing agent be isophorone diamine.
The present invention is further improved by, step 4) in, adopt to enter during shape memory epoxy resin particle with the following method
Capable：By step 4) obtained in solution filtered moisture using vacuum filter, finally at 40～80 DEG C vacuum drying 2～
4h。
The present invention is further improved by, step 4) in, curing agent is instilled equipped with emulsion by dropping funel
In there-necked flask, wherein, there-necked flask is incubated in being positioned over constant water bath box.
The present invention is further improved by, step 4) in, moisture is filtered using vacuum filtration bottle.
Compared with prior art, reacting the shape memory epoxy resin particle for preparing using interfacial polycondensation has following technology special
Point：
1) shape memory epoxy resin particle of the invention is easy to shaping, and reaction speed is fast, and reaction condition is gentle, its
Can be reacted under room temperature.
2) purity requirement of shape memory epoxy resin particle of the invention to reaction monomers is not high, and single to two kinds of reactions
The raw material proportioning of body is required also not sternly, therefore obtained shape memory epoxy resin is particle stabilized.
3) shape memory epoxy resin particle of the invention can be by changing between hydrogenated epoxy resin and toughener
Molecular weight than obtaining different glass transition temperatures, and after knowing the glass transition temperature of material by apply it to tool
In having the bituminous paving of different pavement temperatures.
4) shape memory epoxy resin particle of the invention is incorporated in pitch, considerably increases the elastic recovery of pitch
Performance.
Description of the drawings：
Fig. 1 Fig. 4 is the DSC figures of shape memory epoxy resin particle obtained in the present invention.
Fig. 5 is the FT-IR figures of shape memory epoxy resin particle obtained in the present invention.
Fig. 6 Fig. 9 is the FT-IR figures of shape memory epoxy resin particle obtained in the present invention.
Figure 10 shape memory epoxy resin particles obtained in the present invention are mixed in pitch, and the elastic recovery of pitch is carried
Rise degree figure.
Specific embodiment：
The particular content of the present invention is described in further detail with specific embodiment below in conjunction with the accompanying drawings.
Embodiment 1
90s is preheated at a temperature of 50 DEG C after AL-3040 is mixed with PPGDGE in beaker, oil phase, wherein AL- is obtained
3040 and PPGDGE mol ratio is 19:1, weigh quality is AL-3040 and PPGDGE gross masses 9% gum arabic powder
In beaker, appropriate distilled water is added, 95s is preheated under conditions of 50 DEG C, is obtained water phase, water phase is mixed with oil phase, number is used
Aobvious high-shear homogenizer is instilled curing agent in beaker, is added appropriate distilled water with the rotating speed emulsification 60s of 4000r/min, and stirring is equal
It is even, during the stirring that the there-necked flask with dropping funel is arranged on water bath heat preservation case is arranged, emulsion is moved into there-necked flask
In, aqueous solution of curing agent is moved in dropping funel, the inorganic speed-adjustable stir device of digital display DC is opened, is stirred with the rotating speed of 500r/min
The emulsion in there-necked flask is mixed, while aqueous solution of curing agent is instilled there-necked flask with the speed of 1 drop/s by dropping funel
In；The epoxy particles being molded are filtered moisture with bottle,suction by stirring 1h, obtain shape memory epoxy resin particle, its glass
It is 47.5 DEG C to change transition temperature, compares the pitch do not mixed, and mixes the asphalt elasticity recoverability of shape memory epoxy resin particle
Improve 22.15%.Wherein, curing agent is isophorone diamine, referred to as IPDA, belongs to a kind of normal temperature cure agent, and solidifies
The consumption of agent is determined according under conditions of the quantitative responses such as the reactive hydrogen in the epoxide group in hydrogenated epoxy resin and curing agent
, as 0.5mol.
Embodiment 2
100s is preheated at a temperature of 60 DEG C after AL-3040 is mixed with 0.01PPGDGE in beaker, oil phase is obtained, its
The mol ratio of middle AL-3040 and PPGDGE is 9:1, weigh quality is AL-3040 and PPGDGE gross masses 9.5% Arab
Gum powder in beaker adds appropriate distilled water, preheats 100s, obtain water phase, water phase and oil phase are mixed under conditions of 60 DEG C
Close, with digital display high-shear homogenizer with the rotating speed emulsification 65s of 5000r/min, curing agent is instilled in beaker, appropriate distillation is added
Water, stirs, and during the stirring that the there-necked flask with dropping funel is arranged on water bath heat preservation case is arranged, emulsion is moved into
In there-necked flask, aqueous solution of curing agent is moved in dropping funel, open the inorganic speed-adjustable stir device of digital display DC, with 600r/min
Rotating speed stirring there-necked flask in emulsion, while by dropping funel by aqueous solution of curing agent with the instillation of the speed of 1 drop/s
In there-necked flask；The epoxy particles being molded are filtered moisture with bottle,suction by stirring 2h, obtain shape memory epoxy resin
Grain, its glass transition temperature are 30 DEG C, compare the pitch do not mixed, and the asphalt elasticity for mixing shape memory epoxy resin particle is returned
Renaturation can improve 25.12%.Wherein, curing agent is isophorone diamine, referred to as IPDA, belongs to a kind of normal temperature cure agent,
And the consumption of curing agent is the condition according to quantitative responses such as the reactive hydrogens in the epoxide group in hydrogenated epoxy resin and curing agent
Lower determination, as 0.5mol.
Embodiment 3
2min is preheated at a temperature of 65 DEG C after AL-3040 is mixed with PPGDGE in beaker, oil phase is obtained, wherein,
The mol ratio of AL-3040 and PPGDGE is 5.7:1, weigh quality is AL-3040 and PPGDGE gross masses 8% Arabic tree
Rubber powder in beaker adds appropriate distilled water, preheats 120s, obtain water phase, water phase is mixed with oil phase under conditions of 60 DEG C,
With digital display high-shear homogenizer with the rotating speed emulsification 70s of 6000r/min, curing agent is instilled in beaker, appropriate distilled water is added, is stirred
Mix uniform, during the stirring that the there-necked flask with dropping funel is arranged on water bath heat preservation case is arranged, emulsion is moved into three mouthfuls
In flask, aqueous solution of curing agent is moved in dropping funel, open the inorganic speed-adjustable stir device of digital display DC, turning with 700r/min
Emulsion in speed stirring there-necked flask, while instill three mouthful by aqueous solution of curing agent with the speed of 1 drop/s by dropping funel
In flask；The epoxy particles being molded are filtered moisture with bottle,suction by stirring 3h, obtain shape memory epoxy resin particle, its
Glass transition temperature is 20 DEG C, compares the pitch do not mixed, and mixes the asphalt elasticity recovery of shape memory epoxy resin particle
22.23% can be improved.Wherein, curing agent is isophorone diamine, referred to as IPDA, belongs to a kind of normal temperature cure agent, and solid
The consumption of agent is according to true under conditions of the quantitative responses such as the reactive hydrogen in the epoxide group in hydrogenated epoxy resin and curing agent
Fixed, as 0.5mol.
Embodiment 4
160s is preheated at a temperature of 70 DEG C after AL-3040 is mixed with PPGDGE in beaker, oil phase is obtained, wherein
The mol ratio of AL-3040 and PPGDGE is 4:1, weigh quality is AL-3040 and PPGDGE gross masses 10% Arabic tree
Rubber powder in beaker adds appropriate distilled water, preheats 160s, obtain water phase, water phase is mixed with oil phase under conditions of 70 DEG C,
With digital display high-shear homogenizer with the rotating speed emulsification 60s of 7000r/min, curing agent is instilled in beaker, appropriate distilled water is added, is stirred
Mix uniform, during the stirring that the there-necked flask with dropping funel is arranged on water bath heat preservation case is arranged, emulsion is moved into three mouthfuls
In flask, aqueous solution of curing agent is moved in dropping funel, open the inorganic speed-adjustable stir device of digital display DC, turning with 800r/min
Emulsion in speed stirring there-necked flask, while instill three mouthful by aqueous solution of curing agent with the speed of 1 drop/s by dropping funel
In flask；The epoxy particles being molded are filtered moisture with bottle,suction by stirring 4h, obtain shape memory epoxy resin particle, its
Glass transition temperature is 10 DEG C, compares the pitch do not mixed, and mixes the asphalt elasticity recovery of shape memory epoxy resin particle
19.8% can be improved.Wherein, curing agent is isophorone diamine, referred to as IPDA, belongs to a kind of normal temperature cure agent, and solidifies
The consumption of agent is determined according under conditions of the quantitative responses such as the reactive hydrogen in the epoxide group in hydrogenated epoxy resin and curing agent
, as 0.5mol.
As shown in Fig. 1 to 10, Fig. 1 to Fig. 4 is obtained shape memory epoxy resin under the conditions of 1 embodiment 4 of embodiment
The DSC figures of particle；Wherein, the differential scanning calorimeter (DSC) for being used is Germany's NETZSCH cph60DSC200F3 type differentials
Scanning calorimeter.The glass transition temperature of shape memory epoxy resin particle can be obtained by the glass transition temperature in figure
Degree, AL-3040 are different from the formula of PPGDGE, and the glass transition temperature for obtaining is also different, and with PPGDGE contents
Increase, the glass transition temperature of the shape memory epoxy resin particle of invention reduces.Fig. 5 is 1 embodiment of embodiment, 4 condition
Infrared spectrogram (FT-IR) figure of lower obtained shape memory epoxy resin particle；Wherein, the infrared spectrometer for being used is moral
State Bruker company's T ensor II.387 type infrared spectrometers.It can be seen that the shape memory epoxy resin particle for preparing in figure
In 910cm-1Neighbouring peak vanishes, illustrate that the shape memory epoxy resin particle invented is complete in respective condition of cure
All solidstate.Fig. 6 Fig. 9 is the ESEM of obtained shape memory epoxy resin particle under the conditions of 1 embodiment 4 of embodiment
(SEM) figure；Wherein, the ESEM for being used is Jeol Ltd. JSM-7200F type ESEMs.Can be with from figure
Find out that the shape of shape memory epoxy resin particle obtained in the present invention is more uniform, most of circle for standard.Figure 10 is
Obtained lifting degree of the shape memory epoxy resin particle to asphalt elasticity recoverability under the conditions of 1 embodiment 4 of embodiment,
What abscissa was represented is sample specimens number (being respectively 1-4 from embodiment 1- embodiment 4), and what ordinate was represented is to pitch bullet
The improvement (unit is %) of property recoverability.It can be seen that shape memory epoxy resin particle pair obtained in the present invention
The elastic recovery of pitch has significant improvement, and the shape memory epoxy resin particle of different formulations to pitch bullet
The improvement of property recoverability is different.
Claims (7)
1. a kind of preparation method of shape memory epoxy resin particle, it is characterised in that comprise the following steps：
1) by mol ratio be (4～19):1 hydrogenated epoxy resin is dissolved each other with toughener, at 50～70 DEG C stirring reaction 60～
180s, emulsifying agent is dissolved in distilled water, 30～90s of stirring reaction at 50～70 DEG C, wherein, hydrogenated epoxy resin and toughness reinforcing
The dissolve each other liquid that obtains of agent is oil phase, and the liquid that emulsifying agent is obtained in being dissolved in distilled water is water phase；
2) water phase and oil phase are dissolved each other, in 50～70 DEG C of emulsified 60～150s, stable oil-in-water emulsion is obtained；
3) curing agent is dissolved in distilled water, stirs 30～90s at 30～60 DEG C, aqueous solution of curing agent is obtained；
4) by step 3) obtained in aqueous solution of curing agent dropwise instill step 2) obtained in oil-in-water emulsion, at 50～70 DEG C
1～4h of lower stirring, obtains the epoxy particles being molded, then filters moisture, obtain shape memory epoxy resin particle.
2. a kind of preparation method of epoxy particles according to claim 1, it is characterised in that step 1) in, hydrogenation
Epoxy resin is weathe resistance epoxy resin, and the trade mark is AL-3040, and toughener is polypropylene glycol diglycidyl ether, referred to as
PPGDGE, its molecular weight are 2500, and emulsifying agent is gum arabic powder.
3. a kind of method for preparing epoxy particles according to claim 1, it is characterised in that step 2) in water mutually add
Plus emulsifying agent quality be the 8%～12% of hydrogenated epoxy resin and toughener gross mass.
4. a kind of method for preparing epoxy particles according to claim 1, it is characterised in that step 3) in solidification
Agent is isophorone diamine.
5. a kind of method for preparing epoxy particles according to claim 1, it is characterised in that step 4) in, shape
Adopt what is carried out with the following method during memory epoxy particles：By step 4) obtained in solution filtered water using vacuum filter
Divide, finally 2～4h of vacuum drying at 40～80 DEG C.
6. a kind of method for preparing epoxy particles according to claim 1, it is characterised in that step 4) in, solidification
Agent is instilled in the there-necked flask equipped with emulsion by dropping funel, and wherein, there-necked flask is positioned in constant water bath box
It is incubated.
7. a kind of method for preparing epoxy particles according to claim 1, it is characterised in that step 4) in, adopt
Vacuum filtration bottle filters moisture.
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Cited By (8)
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|---|---|---|---|---|
| CN107353657A (en) * | 2017-08-25 | 2017-11-17 | 南京林业大学 | A kind of method of modifying for improving pitch shape-memory properties |
| CN107418233A (en) * | 2017-08-23 | 2017-12-01 | 南京林业大学 | Improve the method for modifying of mist sealing emulsified asphalt shape-memory properties |
| CN108047653A (en) * | 2017-12-21 | 2018-05-18 | 河南省科学院化学研究所有限公司 | A kind of Toughening Modification of Epoxy micro-sphere material |
| CN108129605A (en) * | 2017-12-21 | 2018-06-08 | 河南省科学院化学研究所有限公司 | A kind of impact resistance epoxide resin microballoon material |
| CN108164657A (en) * | 2018-01-15 | 2018-06-15 | 河南省科学院化学研究所有限公司 | A kind of shape memory epoxy foam |
| CN108947330A (en) * | 2018-08-02 | 2018-12-07 | 西安邮电大学 | A kind of shape memory epoxy resin modified asphalt mixture and preparation method thereof |
| CN109233205A (en) * | 2018-08-31 | 2019-01-18 | 王雪峰 | A kind of preparation method of triple shape memory epoxy resin composite materials |
| CN116178975A (en) * | 2023-03-10 | 2023-05-30 | 南京林业大学 | Preparation method of hydrogenated epoxy resin modified emulsified asphalt |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107418233A (en) * | 2017-08-23 | 2017-12-01 | 南京林业大学 | Improve the method for modifying of mist sealing emulsified asphalt shape-memory properties |
| CN107418233B (en) * | 2017-08-23 | 2019-12-06 | 南京林业大学 | modification method for improving shape memory performance of emulsified asphalt for fog sealing layer |
| CN107353657A (en) * | 2017-08-25 | 2017-11-17 | 南京林业大学 | A kind of method of modifying for improving pitch shape-memory properties |
| CN108047653A (en) * | 2017-12-21 | 2018-05-18 | 河南省科学院化学研究所有限公司 | A kind of Toughening Modification of Epoxy micro-sphere material |
| CN108129605A (en) * | 2017-12-21 | 2018-06-08 | 河南省科学院化学研究所有限公司 | A kind of impact resistance epoxide resin microballoon material |
| CN108164657A (en) * | 2018-01-15 | 2018-06-15 | 河南省科学院化学研究所有限公司 | A kind of shape memory epoxy foam |
| CN108947330A (en) * | 2018-08-02 | 2018-12-07 | 西安邮电大学 | A kind of shape memory epoxy resin modified asphalt mixture and preparation method thereof |
| CN109233205A (en) * | 2018-08-31 | 2019-01-18 | 王雪峰 | A kind of preparation method of triple shape memory epoxy resin composite materials |
| CN116178975A (en) * | 2023-03-10 | 2023-05-30 | 南京林业大学 | Preparation method of hydrogenated epoxy resin modified emulsified asphalt |
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| CN106519567B (en) | 2018-12-04 |
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