CN105906644B - A kind of furyl glycidol ether and its synthetic method and application - Google Patents
A kind of furyl glycidol ether and its synthetic method and application Download PDFInfo
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
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Abstract
The invention discloses a kind of furyl glycidol ether, and shown in structure such as formula (I), in formula (I), R is for C1~C12 alkyl or as shown in formula (II), in formula (II), n=1~10, R1For H, methyl or ethyl.The invention also discloses the preparation method of the furyl glycidol ether.Backbone is carried in the furyl glycidol ether, can assign epoxy resin excellent toughness, the Diels Alder reactions of furans and maleimide have thermal reversibility, the toughness of epoxy resin can be adjusted by being heat-treated.The furyl glycidol ether can be applied to the toughness reinforcing of epoxy resin.
Description
Technical field
The present invention relates to a kind of biological base epoxy, more particularly to a kind of furyl glycidol ether, synthetic method and
It is applied.
Background technology
Epoxy resin is one of most widely used thermosetting resin, and the annual yield in the whole world is at 2,000,000 tons or so at present,
Wherein bisphenol A type epoxy resin accounts for more than 85%.Bisphenol A epoxide resin is mainly by two kinds of raw materials of bisphenol-A and epoxychloropropane
It is made.However, studies have shown that ER albumen can be stimulated by accounting for the bisphenol-A of bisphenol A epoxide resin molecular mass more than 67%
Growth, androgen receptor albumen is damaged, threaten human health.Therefore American-European countries progressively puts into effect related decree, forbids
Bisphenol-A use is in children's container, food beverage containers etc..Moreover, becoming increasingly conspicuous with environmental problem and energy problem, double
For phenol A types epoxy resin as a kind of material dependent on fossil resource, it is non-renewable to the pollution of environment and its raw material
Also more and more paid close attention to by people.
Based on this, the friendly bio-based high polymer material of development environment, the particularly heat cured epoxy resin of bio-based shows
Obtain significant.Such high polymer material is reducing plastic industry to petrochemicals using renewable resource as primary raw material
While dependence, the pollution to environment in petroleum-based feedstock production process is decreased, has and saves petroleum resources and protection ring
The double effects in border, it is the important development direction of current high polymer material.Currently, the research master about bio-based high polymer material
It is confined to some days such as starch plastic, cellulosic-based material, poly butyric valeric acid copolyesters (PHBV), PLA (PLA)
Right macromolecule or thermoplastic, the research for biological based thermoset applications are then relatively fewer.
Recently, Giuseppe etc. has synthesized a kind of epoxy resin of furyl, because its structure is similar to bisphenol-A epoxy
Property, there are the very good mechanical properties different from general bio-based epoxy, receive significant attention, it is considered to be one kind of great potential
Biological base epoxy (Fengshuo Hu；John J.La Scala；Joshua M.Sadler and Giuseppe
R.Palmese, Macromolecules 2014,47 (10), 3332-3342.).
Application No. CN200810198162.5 Chinese patent literature also discloses that a kind of epoxy resin containing furan group
Preparation method, this epoxy is a kind of glycidyl amine epoxy containing furans, and its epoxide equivalent is small, and viscosity is low, processing characteristics
It is excellent, the introducing of furan nucleus, improve the mechanical property of material, heat endurance and chemical resistance.
Due to the rigidity of phenyl ring, cause that internal stress is larger, property is crisp, is also easy to produce crackle after bisphenol A type epoxy resin solidifies, from
And its application in some technical fields is limited, bisphenol A type epoxy resin usually needs toughening modifying in actual applications, tool
The furan type epoxy resin for having similar structure equally has Similar Problems.And above-mentioned application and research are not all carried out to this problem
Discuss and solve.
The content of the invention
The invention provides a kind of furyl glycidol ether and its synthetic method, and the furyl glycidol ether is with length
It chain structure, can assign epoxy resin excellent toughness, and different increasings can be obtained by changing the species for introducing long-chain and length
The epoxy resin of tough effect.
A kind of furyl glycidol ether, shown in structure such as formula (I)：
In formula (I), R is for C1~C12 alkyl or as shown in formula (II)：
In formula (II), n=1~10, R1For H, methyl or ethyl.
The invention also discloses the synthetic method of above-mentioned furans basic ring glycidol ether, comprise the following steps：
(1) maleic anhydride is dissolved in organic solvent A, adds primary amine and carry out amidation process, add after the completion of amidation process
Enter acyl chlorides, imidizate accelerator progress imidization reaction, obtain maleimide；
Described primary amine structure is R-NH2, in formula, R structure is identical with the description of formula (I)；
Described acyl chlorides is one in oxalyl chloride, acryloyl chloride, chloroacetic chloride, trichloro-acetic chloride, chlorobenzoyl chloride, chloracetyl chloride
Kind；
Described imidizate accelerator is at least one of sodium acetate, acetic anhydride, triethylamine, the concentrated sulfuric acid；Described
Organic solvent A is n-hexane, hexamethylene, ether, petroleum ether, dichloromethane, chloroform, ethyl acetate, tetrahydrofuran, dioxy
At least one of six rings, acetone, butanone；
The mol ratio of maleic anhydride and primary amine is 1: 0.5~20；The mol ratio of maleic anhydride and acyl chlorides is 1: 1~5；Malaysia
Acid anhydrides and the mass ratio of organic solvent A are 1: 1~100；
The temperature of amidation process is 0 DEG C~80 DEG C, and the reaction time be 1h~50h, imidization reaction temperature for 0 DEG C~
80 DEG C, the reaction time is 1h~500h；
(2) maleimide, furyl dimethyl carbinol glycidol ether and organic solvent B are mixed, reaction obtains furyl contracting
Water glycerin ether；
The organic solvent B is dichloromethane, chloroform, ethyl acetate, tetrahydrofuran, dioxane, ether, third
At least one of ketone, N, N '-dimethyl formamide, dimethyl sulfoxide (DMSO)；
The mol ratio of described maleimide and furyl dimethyl carbinol glycidol ether is 1: 0.5~10, maleimide
Mass ratio with organic solvent B is 1: 1~100；
Described reaction temperature is 0 DEG C~80 DEG C, and the reaction time is 0.5h~72h.
By the maleimide with long-chain and furan nucleus Diels-Alder reactions occur for the present invention, in furans basic ring
Backbone is introduced in oxygen tree alicyclic monomer, increases the toughness of epoxy resin.
Preferably, in step (1), described acyl chlorides is chloroacetic chloride, one kind in oxalyl chloride, acryloyl chloride, maleic acid
The mol ratio of acid anhydride and acyl chlorides is 1: 1~1.5.
Above-mentioned acyl chlorides has stronger reactivity, and boiling point is relatively low, and excessive acyl chlorides easily removes in post processing.
Preferably, in step (1), described imidizate accelerator is at least one of sodium acetate, triethylamine, horse
The mol ratio for coming acid anhydrides and imidizate accelerator is 1: 1~2.
Preferably, in step (1), described organic solvent A is in ether, dichloromethane, chloroform, tetrahydrofuran
At least one.
Above-mentioned solvent has preferable solubility for reactant, and water content is relatively low in solvent, beneficial to acyl chloride reaction
Progress.
Preferably, in step (1), the mol ratio of maleic anhydride and primary amine is 1: 1~1.2；Described acyl chlorides is oxalyl
The mol ratio of chlorine, maleic anhydride and acyl chlorides is 1: 1~1.5；Described imidizate accelerator is triethylamine, maleic anhydride and acyl
The mol ratio of imidization accelerator is 1: 1~2；Described organic solvent A is dichloromethane, maleic anhydride and organic solvent A
Mass ratio is 1: 2~10.
Under the preferable technical scheme, react and easily carry out and accessory substance is less in course of reaction, the yield of product compared with
Height, in post processing, the accessory substance and excess raw material of reaction are easy to remove, and purification is simple and convenient.
Preferably, in step (1), amidation process and imidization reaction temperature are 0 DEG C~30 DEG C.
The reaction condition is gentle, and accessory substance is few in product, is easily purified, and yield is high.
Preferably, in step (2), described organic solvent B is dichloromethane, chloroform, ethyl acetate, tetrahydrochysene furan
At least one of mutter.
Above-mentioned solvent has preferable dissolubility to reactant, and boiling point is relatively low, is easy to remove.
The invention also discloses application of the above-mentioned furyl glycidol ether in epoxy resin roughening.
The invention also discloses one kind to utilize above-mentioned furyl glycidol ether toughening-modifiedepoxy resin, with weight hundred
Divide than meter, including：
Furyl glycidol ether 40%~50%
Furyl dimethyl carbinol glycidol ether 30%~40%
IPD 10%~30%.
Its preparation method is：By the furyl glycidol ether, furyl dimethyl carbinol glycidol ether and different Fo Er of formula ratio
Ketone diamines solidifies 1h~3h at 50 DEG C~70 DEG C, solidifies 1h~3h at 70 DEG C~90 DEG C, solidify at 100 DEG C~140 DEG C 1h~
10h, obtain toughening-modifiedepoxy resin.
Furans base epoxy has good dielectricity, is more satisfactory electronic package material, but its toughness is not
Enough, the characteristics of impact resistance is poor, limits its application in Electronic Packaging.Toughening-modifiedepoxy resin can be applied to electricity
Sub- encapsulating material.Resin after toughness reinforcing improves its processing characteristics, has expanded the application of furans base epoxy.
Compared with prior art, beneficial effects of the present invention are：
Backbone is introduced in furyl dimethyl carbinol glycidol ether by Diels-Alder reactions, asphalt mixtures modified by epoxy resin can be assigned
The excellent toughness of fat, the species of long-chain and length are introduced by changing can obtain the epoxy resin of different toughening effects, simultaneously
The Diels-Alder of furans and maleimide reactions have thermal reversibility, can be by being heat-treated the tough performance to epoxy resin
It is adjusted.
Brief description of the drawings
Fig. 1 is the hydrogen nuclear magnetic resonance spectrogram of furyl dimethyl carbinol glycidol ether；
Fig. 2 is the hydrogen nuclear magnetic resonance spectrogram of N- hexyl maleimides prepared by embodiment 1；
Fig. 3 is the hydrogen nuclear magnetic resonance spectrogram of furyl glycidol ether prepared by embodiment 1.
Embodiment
Embodiment 1
(1) 100g maleic anhydrides, 1000g dichloromethane, 100g n-hexylamines are well mixed, reacted 8 hours at 30 DEG C,
150g oxalyl chlorides are added dropwise to reaction solution, react 168 hours at 30 DEG C, are finally added dropwise 150g triethylamines in reaction solution, 30
Reacted 24 hours at DEG C, with dichloromethane extraction three times, saturated common salt washing three times, dry, be evaporated under reduced pressure remove dichloromethane
Afterwards, N- hexyl maleimides are obtained；
The hydrogen nuclear magnetic resonance spectrogram for the N- hexyl maleimides being prepared is as shown in Figure 2；
(2) by 100g N- hexyls maleimide, 500g chloroforms and 150g furyl dimethyl carbinol glycidol ethers,
Reacted 24 hours at 30 DEG C, be evaporated under reduced pressure after removing chloroform and obtain the furyl glycidol ether as shown in formula (I), its
In R group be n-hexyl.
The yield of product is 70%, and the epoxide number of product is 0.45 (theoretical epoxy value is 0.475).
The hydrogen nuclear magnetic resonance spectrogram of furyl dimethyl carbinol glycidol ether is as shown in figure 1, product furyl glycidol ether
Hydrogen nuclear magnetic resonance spectrogram is as shown in Figure 3.
Embodiment 2
(1) 100g maleic anhydrides, 1000g dichloromethane, 100g n-hexylamines are well mixed, reacted 6 hours at 40 DEG C,
200g oxalyl chlorides are added dropwise to reaction solution, react 120 hours at 40 DEG C, are finally added dropwise 200g triethylamines in reaction solution, 40
Reacted 24 hours at DEG C, with dichloromethane extraction three times, saturated common salt washing three times, dry, be evaporated under reduced pressure remove dichloromethane
Afterwards, N- hexyl maleimides are obtained；
(2) by 100g N- hexyls maleimide, 500g chloroforms and 150g furyl dimethyl carbinol glycidol ethers,
Reacted 24 hours at 30 DEG C, be evaporated under reduced pressure after removing chloroform and obtain the furyl glycidol ether as shown in formula (I), its
In R group be n-hexyl.
The yield of product is 58%, and the epoxide number of product is 0.46 (theoretical epoxy value is 0.475).
Embodiment 3
(1) 100g maleic anhydrides, 700g acetone, 150g n-Decylamines are well mixed, reacted 8 hours at 40 DEG C, will
100g chloroacetic chlorides are added dropwise to reaction solution, react 240 hours at 40 DEG C, are finally added dropwise 150g acetic anhydrides in reaction solution, 40 DEG C
Lower reaction 50 hours, N- decyl maleimides are obtained after extracting, wash, dry, being evaporated under reduced pressure and remove solvent；
(2) by 100g N- decyls maleimide, 300g ethyl acetate and 100g furyl dimethyl carbinol glycidol ethers,
Reacted 24 hours at 50 DEG C, be evaporated under reduced pressure after removing ethyl acetate and obtain the furyl glycidol ether as shown in formula (I), its
In R group be positive decyl.
The yield of product is 55%, and the epoxide number of product is 0.41 (theoretical epoxy value is 0.419).
Embodiment 4
(1) 100g maleic anhydrides, 700g acetone, 150g n-Decylamines are well mixed, reacted 6 hours at 50 DEG C, will
120g chloroacetic chlorides are added dropwise to reaction solution, react 168 hours at 50 DEG C, are finally added dropwise 200g acetic anhydrides in reaction solution, 50 DEG C
Lower reaction 24 hours, N- decyl maleimides are obtained after extracting, wash, dry, being evaporated under reduced pressure and remove solvent；
(2) by 100g N- decyls maleimide, 300g ethyl acetate and 100g furyl dimethyl carbinol glycidol ethers,
Reacted 24 hours at 50 DEG C, be evaporated under reduced pressure after removing ethyl acetate and obtain the furyl glycidol ether as shown in formula (I), its
In R group be positive decyl.
The yield of product is 43%, and the epoxide number of product is 0.39 (theoretical epoxy value is 0.419).
Embodiment 5
(1) 100g maleic anhydrides, 1000g chloroforms, 100g (2- amino ethoxies) ethanol are well mixed, at 50 DEG C
Lower reaction 8 hours, is added dropwise to reaction solution by 200g phenyllacetyl chlorides, reacts 192 hours at 50 DEG C, be finally added dropwise in reaction solution
150g triethylamines, react 50 hours at 50 DEG C, N- ethoxy oxygen is obtained after extracting, wash, dry, being evaporated under reduced pressure and remove solvent
Ethyl maleimide；
(2) by 100g N- ethoxy oxygen ethyl maleimide, 300g acetone and 130g furyl dimethyl carbinol glycidols
Ether, reacted 24 hours at 60 DEG C, be evaporated under reduced pressure after removing acetone and obtain the furyl glycidol ether as shown in formula (I), its
In R group be ethoxy oxygen ethyl.
The yield of product is 48%, and the epoxide number of product is 0.46 (theoretical epoxy value is 0.471).
Embodiment 6
(1) 100g maleic anhydrides, 1000g chloroforms, 100g (2- amino ethoxies) ethanol are well mixed, at 40 DEG C
Lower reaction 10 hours, is added dropwise to reaction solution by 200g phenyllacetyl chlorides, reacts 204 hours at 40 DEG C, finally dripped in reaction solution
Add 200g triethylamines, reacted 36 hours at 40 DEG C, N- ethoxys are obtained after extracting, wash, dry, being evaporated under reduced pressure and remove solvent
Oxygen ethyl maleimide；
(2) by 100g N- ethoxy oxygen ethyl maleimide, 300g acetone and 130g furyl dimethyl carbinol glycidols
Ether, reacted 24 hours at 60 DEG C, be evaporated under reduced pressure after removing acetone and obtain the furyl glycidol ether as shown in formula (I), its
In R group be ethoxy oxygen ethyl.
The yield of product is 36%, and the epoxide number of product is 0.44 (theoretical epoxy value is 0.471).
Embodiment 7
(1) 100g maleic anhydrides, 800g butanone, 250g 14- amino -3,6,9, the 12- tetra- oxa- tetradecane -1- alcohol are mixed
Close uniform, reacted 16 hours at 60 DEG C, 120g acryloyl chlorides are added dropwise to reaction solution, react 336 hours at 60 DEG C, finally
150g acetic anhydrides are added dropwise in reaction solution, are reacted 48 hours at 60 DEG C, after extracting, wash, dry, being evaporated under reduced pressure and remove solvent
Obtain the oxa- myristyl maleimides of N- (14- hydroxyls) -3,6,9,12- tetra-；
(2) by the oxa- myristyl maleimides of 100g N- (14- hydroxyls) -3,6,9,12- tetra-, 400g tetrahydrofurans
And 80g furyl dimethyl carbinol glycidol ethers, reacted 48 hours at 60 DEG C, be evaporated under reduced pressure after removing tetrahydrofuran and obtain such as formula
(I) the furyl glycidol ether shown in, R group therein are (14- hydroxyls) -3,6,9,12- tetra- oxa- myristyl.
The yield of product is 34%, and the epoxide number of product is 0.35 (theoretical epoxy value is 0.359).
Embodiment 8
(1) 100g maleic anhydrides, 1000g butanone, 250g 14- amino -3,6,9, the 12- tetra- oxa- tetradecane -1- alcohol are mixed
Close uniform, reacted 16 hours at 60 DEG C, 150g acryloyl chlorides are added dropwise to reaction solution, react 336 hours at 60 DEG C, finally
150g acetic anhydrides are added dropwise in reaction solution, are reacted 48 hours at 60 DEG C, after extracting, wash, dry, being evaporated under reduced pressure and remove solvent
Obtain the oxa- myristyl maleimides of N- (14- hydroxyls) -3,6,9,12- tetra-；
(2) by the oxa- myristyl maleimides of 100g N- (14- hydroxyls) -3,6,9,12- tetra-, 400g tetrahydrofurans
And 80g furyl dimethyl carbinol glycidol ethers, reacted 48 hours at 60 DEG C, be evaporated under reduced pressure after removing tetrahydrofuran and obtain such as formula
(I) the furyl glycidol ether shown in, R group therein are (14- hydroxyls) -3,6,9,12- tetra- oxa- myristyl.
The yield of product is 36%, and the epoxide number of product is 0.35 (theoretical epoxy value is 0.359).
The method of testing of style is as follows in application examples and Comparison study example：
Glass transition temperature (Tg) method of testing is as follows：After sample solidification, smash, it is public with plum Teller-support benefit
The MET types differential scanning calorimeter test of department's production, N2Atmosphere, heating rate are 20 DEG C/min；
For tensile strength by stretching test machine determination, sample is I type samples, and size is long 36mm, wide at central parallel
2.5mm, thick 0.4mm, two head breadth 6.5mm, gauge length 20mm.
Application examples 1
Furyl glycidol ether, 15g furyl dimethyl carbinols glycidol ether and the 9g that 20g embodiments 1 are prepared are different
Isophoronediamine is well mixed, and is solidified 2 hours at first solidifying 2 hours, 90 DEG C at 60 DEG C, then 120 DEG C solidify 10 hours, obtain
The furans base epoxy of toughening modifying.Its glass transition is 65 DEG C, tensile strength 65MPa, impact strength 4.5KJ/m2。
Comparison study example 1
35g furyl dimethyl carbinols glycidol ether and 12g IPDs are well mixed, first solidification 2 is small at 60 DEG C
When, solidify 2 hours at 90 DEG C, then 120 DEG C solidify 10 hours, obtain furans epoxy resin.Its glass transition is 70 DEG C, stretching
Intensity 70MPa, impact strength 2.2KJ/m2。
Claims (10)
1. a kind of furyl glycidol ether, it is characterised in that shown in structure such as formula (I)：
In formula (I), R is for C1~C12 alkyl or as shown in formula (II)：
In formula (II), n=1~10, R1For H, methyl or ethyl.
2. a kind of synthetic method of furyl glycidol ether according to claim 1, it is characterised in that including following step
Suddenly：
(1) maleic anhydride is dissolved in organic solvent A, adds primary amine and carry out amidation process, acyl is added after the completion of amidation process
Chlorine, imidizate accelerator carry out imidization reaction, obtain maleimide；
Described primary amine structure is R-NH2, in formula, R structure is identical with the description of formula (I)；
Described acyl chlorides is one kind in oxalyl chloride, acryloyl chloride, chloroacetic chloride, trichloro-acetic chloride, chlorobenzoyl chloride, chloracetyl chloride；
Described imidizate accelerator is at least one of sodium acetate, acetic anhydride, triethylamine, the concentrated sulfuric acid；Described is organic
Solvent orange 2 A is n-hexane, hexamethylene, ether, petroleum ether, dichloromethane, chloroform, ethyl acetate, tetrahydrofuran, dioxy six
At least one of ring, acetone, butanone；
The mol ratio of maleic anhydride and primary amine is 1：0.5~20；The mol ratio of maleic anhydride and acyl chlorides is 1：1~5；Maleic anhydride
Mass ratio with organic solvent A is 1：1~100；
The temperature of amidation process is 0 DEG C~80 DEG C, and the reaction time is 1h~50h, and imidization reaction temperature is 0 DEG C~80
DEG C, the reaction time is 1h~500h；
(2) maleimide, furyl dimethyl carbinol glycidol ether and organic solvent B are mixed, it is sweet that reaction obtains furyl shrink
Oily ether；
The organic solvent B is dichloromethane, chloroform, ethyl acetate, tetrahydrofuran, dioxane, ether, acetone, N,
At least one of N '-dimethyl formamide, dimethyl sulfoxide (DMSO)；
The mol ratio of described maleimide and furyl dimethyl carbinol glycidol ether is 1：0.5~10, maleimide is with having
Solvent B mass ratio is 1：1~100；
Described reaction temperature is 0 DEG C~80 DEG C, and the reaction time is 0.5h~72h.
3. the synthetic method of furyl glycidol ether according to claim 2, it is characterised in that described in step (1)
Acyl chlorides be oxalyl chloride, acryloyl chloride, one kind in chloroacetic chloride, the mol ratio of maleic anhydride and acyl chlorides is 1：1~1.5.
4. the synthetic method of furyl glycidol ether according to claim 2, it is characterised in that described in step (1)
Imidizate accelerator be sodium acetate, at least one of triethylamine, maleic anhydride and the mol ratio of imidizate accelerator
For 1：1~2.
5. the synthetic method of furyl glycidol ether according to claim 2, it is characterised in that described in step (1)
Organic solvent A be ether, dichloromethane, chloroform, at least one of tetrahydrofuran.
6. the synthetic method of furyl glycidol ether according to claim 2, it is characterised in that in step (1), Malaysia
The mol ratio of acid anhydrides and primary amine is 1：1~1.2；Described acyl chlorides is oxalyl chloride, and the mol ratio of maleic anhydride and acyl chlorides is 1：1~
1.5；Described imidizate accelerator is triethylamine, and the mol ratio of maleic anhydride and imidizate accelerator is 1：1~2；Institute
The organic solvent A stated is dichloromethane, and the mass ratio of maleic anhydride and organic solvent A is 1：2~10.
7. the synthetic method of the furyl glycidol ether according to claim 2 or 6, it is characterised in that in step (1),
Amidation process and imidization reaction temperature are 0 DEG C~30 DEG C.
8. the synthetic method of furyl glycidol ether according to claim 2, it is characterised in that described in step (2)
Organic solvent B be chloroform, ethyl acetate, acetone, one kind in tetrahydrofuran.
A kind of 9. application of furyl glycidol ether according to claim 1 in Toughening Epoxy Resin.
10. one kind utilizes furyl glycidol ether toughening-modifiedepoxy resin according to claim 1, its feature exists
In, by weight percentage, including：
The furyl glycidol ether 40%~50% of claim 1
Furyl dimethyl carbinol glycidol ether 30%~40%
IPD 10%~30%.
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| WO2020024426A1 (en) * | 2018-07-30 | 2020-02-06 | 江苏澳盛复合材料科技有限公司 | Carbon fiber surface sizing agent and application thereof |
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| CN109183416B (en) * | 2018-07-24 | 2021-08-24 | 江苏澳盛复合材料科技有限公司 | Water-based carbon fiber sizing agent and preparation method and application thereof |
| CN109524056B (en) * | 2018-10-24 | 2022-11-11 | 苏州冰心文化用品有限公司 | Sequence macromolecule with anti-counterfeiting identification function and preparation method and application thereof |
| CN111234484B (en) * | 2020-01-17 | 2021-11-16 | 中国科学院宁波材料技术与工程研究所 | Full-bio-based degradable polylactic acid/starch composite material and preparation method thereof |
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