CN109180941A - A kind of preparation method of eight functional epoxy's POSS resin of hybrid inorganic-organic and the preparation method of carbon fibre reinforced composite - Google Patents
A kind of preparation method of eight functional epoxy's POSS resin of hybrid inorganic-organic and the preparation method of carbon fibre reinforced composite Download PDFInfo
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- CN109180941A CN109180941A CN201810968052.6A CN201810968052A CN109180941A CN 109180941 A CN109180941 A CN 109180941A CN 201810968052 A CN201810968052 A CN 201810968052A CN 109180941 A CN109180941 A CN 109180941A
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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
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
- C08J5/0405—Reinforcing macromolecular compounds with loose or coherent fibrous material with inorganic fibres
- C08J5/042—Reinforcing macromolecular compounds with loose or coherent fibrous material with inorganic fibres with carbon fibres
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2383/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
- C08J2383/04—Polysiloxanes
- C08J2383/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K7/00—Use of ingredients characterised by shape
- C08K7/02—Fibres or whiskers
- C08K7/04—Fibres or whiskers inorganic
- C08K7/06—Elements
Abstract
A kind of preparation method of eight functional epoxy's POSS resin of hybrid inorganic-organic and the preparation method of carbon fibre reinforced composite, belong to POSS resin making technique field.The method is as follows: organic solvent, tetramethylammonium hydroxide aqueous solution and 2-(3,4 epoxycyclohexyls being added into round-bottomed flask)-ethyl triethoxysilane or 2-(3,4 epoxycyclohexyls)-ethyl trimethoxy silane, it is stirred to react；After reaction, 70% solvent is evaporated using Rotary Evaporators, obtain colorless and transparent liquid.The transparency liquid and epoxy curing agent are mixed and stirred for uniformly infiltrating the fiber twined in transparency liquid to get POSS base epoxy composition, being transferred in mold, begin to warm up solidification to get carbon fibre reinforced composite.Advantages of the present invention: operating procedure is simple, and reaction condition is mild, and raw material is easy to get, at low cost, and yield is high.The carbon fibre reinforced composite of preparation has relatively high interlaminar shear strength at 200 DEG C.
Description
Technical field
The invention belongs to POSS resin making technique fields, and in particular to a kind of eight functional epoxy of hybrid inorganic-organic
The preparation method of POSS resin and the preparation method of carbon fibre reinforced composite.
Background technique
Polyhedral oligomeric sesquialter silane (abbreviation POSS) is a kind of compound of nanoscale cage structure, also known as cubic silicon
Alkane, general molecular formula are (RSiO1.5) n, basic structural unit is-Si-O-, and the scale of entire molecule is minimum between 1 ~ 3nm
Silicon particle.For its molecule using silicon oxygen skeleton as core, eight Si apexes connect organic substituent group, inorganic silicon oxygen skeleton energy
Enough assign that material is good heat-resisting and mechanical performance, peripheral organic group be designed as reactive group for example epoxy group, alkylene,
POSS and organic polymer can be carried out surface key and grafting, copolymerization by reactive group by silanol group, acryloxy etc.
Deng reaction, in conjunction with nanometer size effect, so that POSS modified high molecular polymer is with good performance.
Silsesquioxane has thermal stability, lower glass transition temperatures, highly-breathable, superior dielectric properties, good
Biocompatibility, low high-temperature behavior persistence and special surface property etc..Due to using silsesquioxane functional group's
It is active to generate copolymer with all kinds of high molecular weight reactives, nearly two silsesquioxane containing functional group and its organic polymer phases during the last ten years
Mutually modified research is more and more paid attention to and is flourished, and existing carbon fiber/epoxy resin composite material exists
150 DEG C or less have excellent mechanical property, have extensive use.But its performance is poor at high temperature, limits in electricity
The application of sub- device, aerospace etc..
Summary of the invention
The purpose of the present invention is to solve performance under current carbon fiber/epoxy resin composite material high temperature is poor, in turn
The problem of limiting application provides the preparation method and carbon fiber increasing of a kind of eight functional epoxy's POSS resin of hybrid inorganic-organic
The preparation method of strong composite material, the carbon fibre reinforced composite of preparation its interlaminar shear strength under 200 DEG C of hot conditions
Value may be up to 22.21Mpa.
To achieve the above object, the technical solution adopted by the present invention is as follows:
A kind of preparation method of eight functional epoxy's POSS resin of hybrid inorganic-organic, the method are specific as follows:
At room temperature, 10 ~ 1000mL organic solvent is added into round-bottomed flask, the tetramethyl that 3 ~ 15mL mass fraction is 3 ~ 20%
The 2-(3 of ammonium hydroxide aqueous solution and 5 ~ 100g, 4 epoxycyclohexyls)-ethyl triethoxysilane or 2-(3,4 epoxy hexamethylenes
Base)-ethyl trimethoxy silane, 6 ~ 200h is stirred to react at a temperature of 20 DEG C ~ 90 DEG C；After reaction, by 70% solvent benefit
It is evaporated with Rotary Evaporators, obtain colorless and transparent liquid, i.e. eight functional epoxy's POSS resin of hybrid inorganic-organic.
It is multiple that more than one eight functional epoxy's POSS resins of hybrid inorganic-organic for stating preparation are that matrix prepares fibre reinforced
The method of condensation material, the method are specific as follows:
Eight functional epoxy POSS resin of hybrid inorganic-organic and epoxy curing agent are mixed and stirred at 30 ~ 120 DEG C
It is even to get POSS base epoxy composition, twined 20 ~ 60 circle fibers are infiltrated 3 in POSS base epoxy composition ~
60min is transferred in mold, begins to warm up solidification, 10 DEG C/min of the rate of heat addition, pressurize 50 ~ 150Mpa at 140 DEG C, solidification
Temperature is 80 ~ 200 DEG C, and curing time is 3 ~ 15h to get carbon fibre reinforced composite.
The beneficial effect of the present invention compared with the existing technology is:
(1) present invention prepares eight functional epoxy's POSS resin of hybrid inorganic-organic, operating procedure letter using hydrolysis-condensation reaction
Single, reaction condition is mild, and raw material is easy to get, at low cost, and yield is high.
(2) eight functional epoxy's POSS resin chemical of the hybrid inorganic-organic composition prepared is clear, have unique structure with
Performance can apply the epoxy resin-base in carbon fibre reinforced composite.
(3) carbon fibre reinforced composite prepared has relatively high interlaminar shear strength at 200 DEG C.
Detailed description of the invention
Fig. 1 is the infrared spectrum of eight functional epoxy's POSS resin of hybrid inorganic-organic prepared by embodiment 1；
Fig. 2 is the mass spectrogram of eight functional epoxy's POSS resin of hybrid inorganic-organic prepared by embodiment 1；
Fig. 3 is eight functional epoxy's POSS resin structure figure of hybrid inorganic-organic prepared by the present invention；
Fig. 4 is the TG figure of eight functional epoxy's POSS resin of hybrid inorganic-organic prepared by embodiment 1.
Specific embodiment
Further description of the technical solution of the present invention with reference to the accompanying drawings and examples, and however, it is not limited to this,
All to be modified to technical solution of the present invention or equivalent replacement, range without departing from the spirit of the technical scheme of the invention should all
Cover within the protection scope of the present invention.
Method as described below is accordingly to be regarded as conventional method unless otherwise instructed.The material unless otherwise instructed can be from disclosure
Commercial sources obtain.Embodiment 1 ~ 6 is the preparation case of eight functional epoxy's POSS resin of hybrid inorganic-organic；Embodiment 7 ~ 11
For the preparation case of carbon fibre reinforced composite.
Specific embodiment 1: present embodiment record is a kind of eight functional epoxy's POSS resin of hybrid inorganic-organic
Preparation method, the method is specific as follows:
At room temperature, 10 ~ 1000mL organic solvent is added into round-bottomed flask, the tetramethyl that 3 ~ 15mL mass fraction is 3 ~ 20%
The 2-(3 of ammonium hydroxide aqueous solution and 5 ~ 100g, 4 epoxycyclohexyls)-ethyl triethoxysilane or 2-(3,4 epoxy hexamethylenes
Base)-ethyl trimethoxy silane, 6 ~ 200h is stirred to react at a temperature of 20 DEG C ~ 90 DEG C；After reaction, by 70% solvent benefit
It is evaporated with Rotary Evaporators, colorless and transparent liquid, i.e. eight functional epoxy's POSS resin of hybrid inorganic-organic are obtained, is produced
Rate is 89.4%.The present invention utilizes 2-(3,4 epoxycyclohexyls)-ethyl triethoxysilane or 2-(3,4 epoxycyclohexyls)-second
Base trimethoxy silane is monomer, and with tetrahydrofuran etc. for solvent, by hydrolysis-condensation reaction, being prepared for POSS is kernel, 8
The eight functional epoxy POSS resin of hybrid inorganic-organic (structure such as Fig. 3) that siloxane chain is arm, epoxy group is end group.
Specific embodiment 2: a kind of eight functional epoxy POSS tree of hybrid inorganic-organic described in specific embodiment one
The preparation method of rouge, the organic solvent is toluene, dimethylbenzene, ethylbenzene, acetone, butanone, tetrahydrofuran, methanol, ethyl alcohol, different
One or more of propyl alcohol.The polarity of solvent has very big influence to the hydrolysis and condensation of siloxanes, and siloxanes hydrolysis produces
Hydroxyl is given birth to, will form the progress that hydrogen bond hinders following condensation reaction between hydroxyl, the appropriate polarity for increasing solvent can weaken
Hydrogen bond action is conducive to the polarity of reaction；But if solvent polarity is excessive, it is condensed intermediate product poor solubility in a solvent,
It is unfavorable for continuing for condensation, therefore selects the above solvent, at low cost and yield is high.
Specific embodiment 3: a kind of eight functional epoxy of hybrid inorganic-organic prepared with specific embodiment one or two
POSS resin is the method that matrix prepares carbon fibre reinforced composite, and the method is specific as follows:
Eight functional epoxy POSS resin of hybrid inorganic-organic and epoxy curing agent are mixed and stirred at 30 ~ 120 DEG C
It is even to get POSS base epoxy composition, twined 20 ~ 60 circle fibers are infiltrated 3 in POSS base epoxy composition ~
60min is transferred in mold, begins to warm up solidification, 10 DEG C/min of the rate of heat addition, pressurize 50 ~ 150Mpa at 140 DEG C, solidification
Temperature is 80 ~ 200 DEG C, can select three temperature as cure stage wherein, and curing time is 3 ~ 15h to get fibre reinforced
Composite material.
Specific embodiment 4: a kind of method for preparing carbon fibre reinforced composite described in specific embodiment three,
The mass ratio of the eight functional epoxy POSS resin of hybrid inorganic-organic and epoxy curing agent is 100: 5 ~ 50.
Specific embodiment 5: a kind of method for preparing carbon fibre reinforced composite described in specific embodiment three,
The fiber is one of T300, T800, T1000, M40J, graphite fibre.
Specific embodiment 6: a kind of method for preparing carbon fibre reinforced composite described in specific embodiment three,
The epoxy curing agent is 3,3'- diethyl 4,4'- diaminodiphenyl-methane, triethylene tetramine, 4.4 diamino of DDM
One of base diphenyl-methane, dioctyl phthalate, m-phenylene diamine (MPD).
For traditional POSS since viscosity is too big, interfacial bonding is indifferent can not to be used as resin matrix.The present invention is in technique
On done certain innovation: (1) from the point of view of wellability, the present invention used in POSS contain certain solvent, solvent content 30%
~ 50%, resin Experimental is infiltrated by fiber and shows the imbibition characteristic for having excellent.(2) from the point of view of interface cohesion degree, at 140 DEG C
Pressurized deflation removes the solvent in resin, the i.e. close not starved again of composite material obtained.And DSC cure characteristic shows 180
It DEG C is exothermic maximum point.The composite material is at low cost, and simple process can be mass, it is most important that with hybrid inorganic-organic
Eight functional epoxy's POSS resins are that carbon fibre reinforced composite made of matrix has fabulous interlaminar shear strength at high temperature.
Main cause is that epoxy group POSS kernel is made of inorganic-Si-O-Si-, so having good heat resistance, TG curve is such as
Shown in Fig. 4, temperature when mass loss 5% is 423 DEG C.
Embodiment 1:
2-(3,4 epoxycyclohexyls that quality is 10g are sequentially added into round-bottomed flask)-ethyl triethoxysilane, 80mL be different
The tetramethylammonium hydroxide aqueous solution that propyl alcohol, 20mL dimethylbenzene and 5g mass fraction are 5%, is stirred to react 8h at 90 DEG C；Reaction
After, 70% solvent is evaporated using Rotary Evaporators, obtain colorless and transparent liquid, i.e. hybrid inorganic-organic eight
Functional epoxy's POSS resin；Product quality is 4.98g, yield 81.1%.
The infared spectrum of eight functional epoxy's POSS resin of hybrid inorganic-organic is as shown in Fig. 2, matter obtained in embodiment 1
Spectrum is as shown in Figure 1.
Embodiment 2:
2-(3,4 epoxycyclohexyls that quality is 10g are sequentially added into round-bottomed flask)-ethyl triethoxysilane, 80mL be different
The tetramethylammonium hydroxide aqueous solution that propyl alcohol, 20mL dimethylbenzene and 5g mass fraction are 5%, is stirred to react 48h at 30 DEG C；Instead
It is after answering, 70% solvent is evaporated using Rotary Evaporators, obtain colorless and transparent liquid, i.e. hybrid inorganic-organic
Eight functional epoxy's POSS resins；Product quality is 5.11g, yield 83.1%.
Embodiment 3:
2-(3,4 epoxycyclohexyls that quality is 10g are sequentially added into round-bottomed flask)-ethyl triethoxysilane, 80mL be different
The tetramethylammonium hydroxide aqueous solution that propyl alcohol, 20mL dimethylbenzene and 5g mass fraction are 8%, is stirred to react 100h at 30 DEG C；Instead
It is after answering, 70% solvent is evaporated using Rotary Evaporators, obtain colorless and transparent liquid, i.e. hybrid inorganic-organic
Eight functional epoxy's POSS resins；Product quality is 5.41g, yield 87.9%.
Embodiment 4:
2-(3,4 epoxycyclohexyls that quality is 20g are sequentially added into round-bottomed flask)-ethyl triethoxysilane, 40mL be different
The tetramethylammonium hydroxide aqueous solution that propyl alcohol, 60mL dimethylbenzene and 5g mass fraction are 8%, is stirred to react 48h at 30 DEG C；Instead
It is after answering, 70% solvent is evaporated using Rotary Evaporators, obtain colorless and transparent liquid, i.e. hybrid inorganic-organic
Eight functional epoxy's POSS resins；Product quality is 5.24g, yield 85.3%.
Embodiment 5:
2-(3,4 epoxycyclohexyls that quality is 10g are sequentially added into round-bottomed flask)-ethyl trimethoxy silane, 40mL be different
The tetramethylammonium hydroxide aqueous solution that propyl alcohol, 60mL dimethylbenzene and 5g mass fraction are 8%, is stirred to react 100h at 30 DEG C；Instead
It is after answering, 70% solvent is evaporated using Rotary Evaporators, obtain colorless and transparent liquid, i.e. hybrid inorganic-organic
Eight functional epoxy's POSS resins；Product quality is 5.34g, yield 87.0%.
Embodiment 6:
2-(3,4 epoxycyclohexyls that quality is 10g are sequentially added into round-bottomed flask)-ethyl trimethoxy silane, 100mL tetra-
The tetramethylammonium hydroxide aqueous solution that hydrogen furans and 5g mass fraction are 8%, is stirred to react 100h at 30 DEG C；After reaction,
70% solvent is evaporated using Rotary Evaporators, obtain colorless and transparent liquid, i.e. eight function ring of hybrid inorganic-organic
Oxygen POSS resin；Product quality is 5.49g, yield 89.4%.
The infared spectrum of eight functional epoxy's POSS resin of hybrid inorganic-organic is as shown in Fig. 2, matter obtained in embodiment 6
Spectrum is as shown in Figure 1.
Embodiment 7:
By the resulting eight functional epoxy POSS resin of 20g hybrid inorganic-organic of embodiment 1 and 2.5g 3,3'- diethyl at 90 DEG C
Base 4,4'- diaminodiphenyl-methane are mixed and stirred for uniformly enclosing winding 20 to get POSS base epoxy composition
T300 carbon fiber infiltrates 5min in POSS base epoxy composition, is transferred in mold, begins to warm up, the rate of heat addition 10
DEG C/min, in 140 DEG C of pressurization 100Mpa, solidification temperature is 140 DEG C, and curing time is 10h to get carbon fiber reinforced plastic
Material.Molding thickness about 2mm, resin content about 30%.Its interlaminar shear strength 20.32Mpa is surveyed at 200 DEG C.
Embodiment 8:
By the resulting eight functional epoxy POSS resin of 20g hybrid inorganic-organic of embodiment 1 and 4.7g 3,3'- diethyl at 80 DEG C
Base 4,4'- diaminodiphenyl-methane are mixed and stirred for uniformly enclosing winding 25 to get POSS base epoxy composition
T300 carbon fiber infiltrates 10min in POSS base epoxy composition, is transferred in mold, begins to warm up, the rate of heat addition 10
DEG C/min, in 140 DEG C of pressurization 100Mpa, solidification temperature is 160 DEG C, and curing time is 8h to get carbon fibre reinforced composite.
Molding thickness about 2mm, resin content about 30%.Its interlaminar shear strength 22.21Mpa is surveyed at 200 DEG C.
Embodiment 9:
By the resulting eight functional epoxy POSS resin of 20g hybrid inorganic-organic of embodiment 1 and 7.2g 3,3'- diethyl at 70 DEG C
Base 4,4'- diaminodiphenyl-methane are mixed and stirred for uniformly enclosing winding 30 to get POSS base epoxy composition
T300 carbon fiber infiltrates 15min in POSS base epoxy composition, is transferred in mold, begins to warm up, the rate of heat addition 10
DEG C/min, in 140 DEG C of pressurization 100Mpa, solidification temperature is 180 DEG C, and curing time is 7h to get carbon fibre reinforced composite.
Molding thickness about 2mm or so, resin content about 30%.Its interlaminar shear strength 17.22Mpa is surveyed at 200 DEG C.
Embodiment 10:
By the resulting eight functional epoxy POSS resin of 20g hybrid inorganic-organic of embodiment 1 and 8.3g 3,3'- diethyl at 60 DEG C
Base 4,4'- diaminodiphenyl-methane are mixed and stirred for uniformly enclosing winding 35 to get POSS base epoxy composition
T300 carbon fiber infiltrates 20min in POSS base epoxy composition, is transferred in mold, begins to warm up, the rate of heat addition 10
DEG C/min, in 140 DEG C of pressurization 100Mpa, solidification temperature is 190 DEG C, and curing time is 6h to get carbon fibre reinforced composite.
Molding thickness about 2mm or so, resin content about 30%.Its interlaminar shear strength 19.76Mpa is surveyed at 200 DEG C.
Embodiment 11:
By the resulting eight functional epoxy POSS resin of 20g hybrid inorganic-organic of embodiment 1 and 9.6g 3,3'- diethyl at 50 DEG C
Base 4,4'- diaminodiphenyl-methane are mixed and stirred for uniformly enclosing winding 40 to get POSS base epoxy composition
T300 carbon fiber infiltrates 30min in POSS base epoxy composition, is transferred in mold, begins to warm up, the rate of heat addition 10
DEG C/min, in 140 DEG C of pressurization 100Mpa, solidification temperature is 200 DEG C, and curing time is 5h to get carbon fibre reinforced composite.
Molding thickness about 2mm or so, resin content about 30%.Its interlaminar shear strength 18.69Mpa is surveyed at 200 DEG C.
Claims (6)
1. a kind of preparation method of eight functional epoxy's POSS resin of hybrid inorganic-organic, it is characterised in that: the method is specifically such as
Under:
At room temperature, 10 ~ 1000mL organic solvent is added into round-bottomed flask, the tetramethyl that 3 ~ 15mL mass fraction is 3 ~ 20%
The 2-(3 of ammonium hydroxide aqueous solution and 5 ~ 100g, 4 epoxycyclohexyls)-ethyl triethoxysilane or 2-(3,4 epoxy hexamethylenes
Base)-ethyl trimethoxy silane, 6 ~ 200h is stirred to react at a temperature of 20 DEG C ~ 90 DEG C；After reaction, by 70% solvent benefit
It is evaporated with Rotary Evaporators, obtain colorless and transparent liquid, i.e. eight functional epoxy's POSS resin of hybrid inorganic-organic.
2. a kind of preparation method of eight functional epoxy's POSS resin of hybrid inorganic-organic according to claim 1, feature
Be: the organic solvent is toluene, in dimethylbenzene, ethylbenzene, acetone, butanone, tetrahydrofuran, methanol, ethyl alcohol, isopropanol
It is one or more of.
3. a kind of eight functional epoxy's POSS resin of hybrid inorganic-organic using claims 1 or 2 preparation prepares carbon fiber as matrix
Enhance the method for composite material, it is characterised in that: the method is specific as follows:
Eight functional epoxy POSS resin of hybrid inorganic-organic and epoxy curing agent are mixed and stirred at 30 ~ 120 DEG C
It is even to get POSS base epoxy composition, twined 20 ~ 60 circle fibers are infiltrated 3 in POSS base epoxy composition ~
60min is transferred in mold, begins to warm up solidification, 10 DEG C/min of the rate of heat addition, pressurize 50 ~ 150Mpa at 140 DEG C, solidification
Temperature is 80 ~ 200 DEG C, and curing time is 3 ~ 15h to get carbon fibre reinforced composite.
4. a kind of method for preparing carbon fibre reinforced composite according to claim 3, it is characterised in that: described has
The mass ratio of eight functional epoxy POSS resin of machine-inorganic hybridization and epoxy curing agent is 100: 5 ~ 50.
5. a kind of method for preparing carbon fibre reinforced composite according to claim 3, it is characterised in that: the fibre
Dimension is one of T300, T800, T1000, M40J, graphite fibre.
6. a kind of method for preparing carbon fibre reinforced composite according to claim 3, it is characterised in that: the ring
Oxygen resin curing agent is 3,3'- diethyl 4,4'- diaminodiphenyl-methane, triethylene tetramine, 4.4 diamino hexichol first of DDM
One of alkane, dioctyl phthalate, m-phenylene diamine (MPD).
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| CN110483781A (en) * | 2019-09-10 | 2019-11-22 | 哈尔滨工业大学 | A kind of preparation method of polyhydroxy propyl POSS |
| KR102164845B1 (en) * | 2020-04-29 | 2020-10-13 | (주)필스톤 | Polyhedral Oligomeric Silsesquioxane Having Epoxy Functional Group and Method Of Manufacturing |
| CN115404043A (en) * | 2022-09-29 | 2022-11-29 | 安田信邦（厦门）电子科技有限公司 | High-toughness high-thermal-stability flame-retardant electronic packaging adhesive and preparation method thereof |
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| 任亚国: "环氧基倍半硅氧烷（POSS）的合成及其酯化性能研究", 《中国优秀硕士学位论文全文数据库工程科技I辑》 * |
| 赵容等: "环氧基笼型倍半硅氧烷的合成研究", 《热固性树脂》 * |
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| CN109853234A (en) * | 2019-03-12 | 2019-06-07 | 深圳华力兴新材料股份有限公司 | It is a kind of to improve the method for carbon fiber insulation performance, modified carbon fiber and application thereof |
| CN109853234B (en) * | 2019-03-12 | 2022-01-04 | 深圳华力兴新材料股份有限公司 | Method for improving insulating property of carbon fiber, modified carbon fiber and application thereof |
| CN110483781A (en) * | 2019-09-10 | 2019-11-22 | 哈尔滨工业大学 | A kind of preparation method of polyhydroxy propyl POSS |
| KR102164845B1 (en) * | 2020-04-29 | 2020-10-13 | (주)필스톤 | Polyhedral Oligomeric Silsesquioxane Having Epoxy Functional Group and Method Of Manufacturing |
| CN115404043A (en) * | 2022-09-29 | 2022-11-29 | 安田信邦（厦门）电子科技有限公司 | High-toughness high-thermal-stability flame-retardant electronic packaging adhesive and preparation method thereof |
| CN115404043B (en) * | 2022-09-29 | 2024-01-12 | 安田信邦（厦门）电子科技有限公司 | High-toughness high-thermal-stability flame-retardant electronic packaging adhesive and preparation method thereof |
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