CN110423350A - A kind of high-fire resistance silicon substrate benzyne resin of low-temperature setting and its preparation method and application - Google Patents
A kind of high-fire resistance silicon substrate benzyne resin of low-temperature setting and its preparation method and application Download PDFInfo
- Publication number
- CN110423350A CN110423350A CN201910625516.8A CN201910625516A CN110423350A CN 110423350 A CN110423350 A CN 110423350A CN 201910625516 A CN201910625516 A CN 201910625516A CN 110423350 A CN110423350 A CN 110423350A
- Authority
- CN
- China
- Prior art keywords
- resin
- silicon substrate
- benzyne
- low
- fire resistance
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- 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
- C08G77/06—Preparatory processes
-
- 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
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions 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; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on 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; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/18—Fireproof paints including high temperature resistant paints
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Silicon Polymers (AREA)
Abstract
The invention belongs to resin technology fields, and in particular to a kind of high-fire resistance silicon substrate benzyne resin of low-temperature setting and preparation method thereof.The resin is with 1; 3,5- tri- acetylenylbenzenes, diacetylenic benzene, dimethyl dichlorosilane (DMCS) are primary raw material, under the protection of inert gas; using the synthetic method of Grignard Reagent, prepare and obtained a series of high-fire resistances using acetenyl as the silicon substrate benzyne resin of terminal groups.The resin is soluble in common solvent such as toluene, tetrahydrofuran etc.;Modest viscosity under room temperature, fusing point are low;Processing temperature is 20 DEG C -155 DEG C, has good processing performance;Solidification temperature is lower than 115 DEG C, and 5% decomposition temperature of resin cured matter can reach 684.8 DEG C, suitable for preparing high-performance composite materials matrix, high-temperaure coating and photoelectric material, can be applied to spacecraft and field of photovoltaic materials.
Description
Technical field
The invention belongs to resin technology fields, and in particular to the high-fire resistance silicon substrate benzyne resin of low-temperature setting a kind of and
Preparation method and application.
Background technique
High temperature resistant hybrid resin containing element silicon becomes research hotspot with its excellent heat resistance and dielectric properties.It introduces
The aryl polyyne resin of element silicon, special composition and molecular structure make it collect Characteristics of Organic and inorganic matter function in one
Body, the introducing of element silicon not only makes polymer have excellent heat resistance, and has excellent dielectric properties and refractory ceramics
Change performance.Can be used for preparing ceramic precursor, high-performance composite materials matrix, high temperature resistant ablator etc., spacecraft,
The fields such as photoelectric material have broad application prospects.It is solid in MgO that Itoh [1] has studied monosubstituted acetylenic monomer and silane containing hydrogen
Dehydrogenation coupling reaction under the catalytic condition of body catalyst, obtains siliceous aryne resin.5% point under the conditions of argon gas of the resin
Solution temperature is up to 860 DEG C, and 1000 DEG C of thermal decomposition residual rate is more than 90%, and heat resistance is very excellent;Its excellent high heat resistance
Cyclotrimerization of the performance between-hydrosilylation between Si -- H bond and-C ≡ CH, Ph-C ≡ CH and-CH ≡ CH with
And Diels-Alder reaction is formed by complex cross-linked network;Its disadvantage is that solidification temperature height, process window are relatively narrow.Yan Hao
[2] research is modified to poly- aryl polyyne using organosilan, using halogenated silanes and aryl ethane as raw material, has synthesized novelty
The aryl polyyne resin of structure;It is liquid or the solid of low melting point, resin cured matter fine heat-resisting performance under resin room temperature.Ginger
Vigorously [3] are catalyzed by zinc chloride using a diacetylenic benzene, bis- (dimethylamino) dimethylsilanes as raw material and realize single step silanization
Synthesize siliceous aryne resin;Resin product is in flow regime at normal temperature, and processing temperature is 40~180 DEG C, and process window is very
It is wide;But resin cured matter is in N25% decomposition temperature (T under atmosphered5) it is 587 DEG C, it need further to study heat-resisting to enhance its
Performance.
Summary of the invention
The purpose of the present invention is to provide high-fire resistance silicon substrate benzyne resin of a kind of low-temperature setting and preparation method thereof and
Using solving the problems, such as that resin cure temperature is excessively high, synthesized a kind of silicon substrate benzyne resin of novel high heat resistant.
The technical scheme is that
A kind of high-fire resistance silicon substrate benzyne resin of low-temperature setting, the high-fire resistance resin have the following structure, the former
It is the product structure formula (embodiment 1) that 1,3,5- tri- acetylenylbenzenes and dimethyl dichlorosilane (DMCS) react, the latter is a diacetylene
The product structure formula that the mixture of tri- acetylenylbenzene of base benzene and 1,3,5- is copolymerized with dimethyl dichlorosilane (DMCS) (is implemented
Example 2-4).
Or
The present invention also provides a kind of preparation methods of the high-fire resistance silicon substrate benzyne resin of above-mentioned low-temperature setting, mainly walk
Suddenly are as follows:
(1) under inert gas protection, the reaction of magnesium powder and bromoethane generates ethylmagnesium bromide Grignard Reagent;
(2) above-mentioned reaction product and alkynyl class monomer reaction generate acetenyl magnesium bromide Grignard Reagent;
(3) above-mentioned reaction product is reacted with dimethyl dichlorosilane (DMCS), obtains the silicon substrate benzyne resin that both ends are acetenyl sealing end.
The preparation method of the high-fire resistance silicon substrate benzyne resin of the low-temperature setting according to the present invention further contains alkynyl
The molar ratio of class monomer and dimethyl dichlorosilane (DMCS) is 1:1, the molar ratio difference of diacetylenic benzene and tri- acetylenylbenzene of 1,3,5-
For 0:1,2:1,5:1,10:1, the monomer of class containing alkynyl is a diacetylenic benzene and 1,3,5- tri- acetylenylbenzenes.
Further, the molar ratio of bromoethane and alkynyl in the investment monomer of class containing alkynyl is 1.1:1, and magnesium powder and investment are containing alkynyl
It is 1.0-1.3:1 that the molar ratio of alkynyl, which is ratio, in class monomer, and optimal feed ratio is 1.2:1.
The monomer of class containing alkynyl used is tri- acetylenylbenzene of a diacetylenic benzene and 1,3,5-
The preparation method of the high-fire resistance silicon substrate benzyne resin of the low-temperature setting according to the present invention contains alkynyl by adjusting
The input ratio of class monomer and silane adjusts molecular resin chain length, and controlling in polymer may participate in the close of curing reaction functional group
The content of silicon in degree, structure.
The value of m and n is controlled by the ingredient proportion of tri- acetylenylbenzene of diacetylenic benzene and 1,3,5- in the present invention
System, i.e., between diacetylenic benzene proportion it is bigger, the value of m is bigger.
Further, it synthesizes solvent used in alkynes Grignard Reagent and is generally tetrahydrofuran (THF), 2- methyltetrahydrofuran, first
Benzene.Preferably 2- methyltetrahydrofuran, because acetylenic monomer dissolubility in 2- methyltetrahydrofuran is good.
The present invention also provides a kind of high-fire resistance silicon substrate benzyne resin of low-temperature setting or above-mentioned preparation method systems
The high-fire resistance silicon substrate benzyne resin of the low-temperature setting obtained, is preparing high-performance composite materials matrix, high-temperaure coating and photoelectricity
Application on material.
The present invention also provides a kind of high-fire resistance silicon substrate benzyne resin of low-temperature setting or above-mentioned preparation method systems
The high-fire resistance silicon substrate benzyne resin of the low-temperature setting obtained, in the application of spacecraft and field of photovoltaic materials.
Silane used in studying is dimethyl dichlorosilane (DMCS).
Before reaction starts, used reagent will be dried, while the vapor in removing device and logical nitrogen guarantor
Shield.
The synthesis of ethylmagnesium bromide Grignard Reagent: being added to four-hole boiling flask for magnesium powder and 2- methyltetrahydrofuran, slowly drips
Add the mixed solution of bromoethane and 2- methyltetrahydrofuran.After dripping, 45 DEG C of isothermal reaction 2h.
The synthesis of alkynyl magnesium bromide Grignard Reagent: be slowly added dropwise into ethylmagnesium bromide Grignard Reagent the monomer of class containing alkynyl and
The mixed solution of 2- methyltetrahydrofuran.After dripping, 82 DEG C of isothermal reaction 2h.
Under nitrogen protection, dimethyl dichlorosilane (DMCS), 45 DEG C of isothermal reaction 1h, 82 DEG C of isothermal reactions are added dropwise in Xiang Shangshu product
2h.Generate the silicon substrate benzyne resin of acetenyl sealing end.
Synthetic resin has a structure that
Or
After reaction terminates, glacial acetic acid is added and dilute hydrochloric acid, system gradually generate precipitating.Methyl tertiary butyl ether(MTBE) is added, stirs
Mix 10min.Troubled liquor is transferred to separatory funnel, appropriate amount of deionized water is added, precipitating disappears, and system becomes orange-yellow transparent
State.It shakes up, stratification, the liquid for releasing lower layer.It repeats the above steps washing 4~5 times, until neutral.
Anhydrous sodium sulfate dry 12h, filtering, vacuum distillation are added in above-mentioned product, finally obtains the thick tree of yellowish-brown
Rouge.
The formula and synthesis step of resin preparation of the present invention are following (in parts by weight): 6~8 parts of bromoethanes, 1~2
Part magnesium powder, 20~25 parts of 2- methyltetrahydrofurans, react 2h under the conditions of 40~50 DEG C, synthesize ethylmagnesium bromide Grignard Reagent;
Diacetylenic benzene and tri- acetylenylbenzene of 1,3,5- and the mixing of 55~65 parts of 2- methyltetrahydrofuran are molten between being added dropwise 3~5 parts later
Liquid synthesizes alkynyl magnesium bromide Grignard Reagent under the conditions of 82 DEG C;Then 5~8 parts of dimethyl dichlorosilane (DMCS)s and 10~15 parts are added dropwise
2- methyltetrahydrofuran reacts 1h under the conditions of 45 DEG C, then increases temperature to 2h is reacted under the conditions of 82 DEG C, and institute is finally prepared
State silicon substrate benzyne resin.
Compared to existing modified silicon-contained aryne resin, silicon substrate benzyne resin prepared by the present invention is had the following characteristics that
Dissolubility is good, and processing performance is good;Low-temperature setting, curing time are short;Resin cured matter is heat-resist.
The resin is soluble in common solvent, and modest viscosity under room temperature, fusing point is low, and processing performance is good.Solidification temperature is low
In 115 DEG C, 5% decomposition temperature of resin cured matter can reach 684 DEG C, suitable for preparing high-performance composite materials matrix, resistance to
High temperature coating and photoelectric material can be applied to spacecraft and field of photovoltaic materials.
Detailed description of the invention
The hydrogen nuclear magnetic resonance spectrogram of 1 resin of Fig. 1 embodiment;
The Fourier transform infrared spectroscopy figure of resin in Fig. 2 embodiment 1.
Specific embodiment
Below with reference to specific example, the present invention is described in detail, following embodiment facilitate those skilled in the art into
One step understands the present invention, but the invention is not limited in any way.It should be pointed out that coming to those skilled in the art
It says, without departing from the inventive concept of the premise, various modifications and improvements can be made.These belong to protection of the invention
Range.
Embodiment 1
1.73g magnesium powder (0.072mol) and 10mL2- methyltetrahydrofuran are added to four-hole boiling flask, 7.19g is slowly added dropwise
Bromoethane (0.066mol) and 10mL2- methyltetrahydrofuran.After dripping, 45 DEG C of isothermal reaction 2h.It is slowly added dropwise 3.0g's
1,3,5- tri- acetylenylbenzene (0.02mol) and 50mL2- methyltetrahydrofuran mixed solution, 82 DEG C of isothermal reaction 2h.It is added dropwise
2.30g dimethyl dichlorosilane (DMCS) (0.02mol) and 30mL2- methyltetrahydrofuran, 45 DEG C of isothermal reaction 1h are warming up to 82 DEG C of constant temperature
React 2h.2mL glacial acetic acid and 2mL dilute hydrochloric acid are added dropwise again, stirs 0.5h.Methyl tertiary butyl ether(MTBE) is added as solvent, addition is gone
Ionized water is washed five to eight times.With the dry 10h of anhydrous sodium sulfate, after filtering, vacuum distillation obtains pale brown chromoresin, has one
Fixed mobility, resin viscosity are moderate.1H-NMR result :-Si-CH3Chemical shift is in 0.4~0.5ppm ,-C ≡ CH chemical shift
In 3.09ppm ,-Si-H chemical shift is in 4.5ppm;FT-IR result: 3296cm-1- C ≡ CH stretching vibration peak is belonged to,
2964cm-1Belong to-Si-CH3 stretching vibration peak, 2165cm-1Belong to the stretching vibration peak of-C ≡ C- He-Si-H.It is resulting
Resin-soluble is in toluene.Program curing are as follows: 115 DEG C/1h, 130 DEG C/1h, 150 DEG C/2h, 170 DEG C/2h, 200 DEG C/2h.Resin
After solidification, the blocks of solid of bright black densification is obtained.5% decomposition temperature of resin cured matter is 560.2 DEG C, and 800 DEG C of residual rates are
90.2%.
Embodiment 2
4.032g magnesium powder (0.168mol) and 10mL2- methyltetrahydrofuran are added to four-hole boiling flask, are slowly added dropwise
16.78g bromoethane (0.154mol) and 10mL2- methyltetrahydrofuran.After being added dropwise, 45 DEG C of isothermal reaction 2h.It is slowly added dropwise
Tri- acetylenylbenzene of 1,3,5- (0.02mol) and 40mL2- methyl tetrahydro of diacetylenic benzene (0.04mol) and 3.00g between 5.04g
Furans mixed solution, 82 DEG C of isothermal reaction 2h.6.90g dimethyl dichlorosilane (DMCS) (0.06mol) and 30mL2- methyl tetrahydro furan is added dropwise
It mutters, 45 DEG C of isothermal reaction 1h are warming up to 82 DEG C of isothermal reaction 2h.Other steps finally obtain yellowish-brown chromoresin with embodiment 1,
Resin is in medium-viscosity state at room temperature.
1H-NMR result and FT-IR result are the same as embodiment 1.Resulting resin-soluble is in toluene.Program curing are as follows: 115
DEG C/1h, 130 DEG C/1h, 150 DEG C/2h, 170 DEG C/2h, 200 DEG C/2h.After resin solidification, the bulk for obtaining bright black densification is solid
Body.5% decomposition temperature of resin cured matter is 562.4 DEG C, and 800 DEG C of residual rates are 88.4%.
Embodiment 3
7.488g magnesium powder (0.312mol) and 10mL2- methyltetrahydrofuran are added to four-hole boiling flask, are slowly added dropwise
31.59g bromoethane (0.286mol) and 10mL2- methyltetrahydrofuran.After dripping, 45 DEG C of isothermal reaction 2h.It is slowly added dropwise
Tri- acetylenylbenzene of 1,3,5- (0.02mol) and 50mL2- methyl tetrahydro of diacetylenic benzene (0.1mol) and 3.00g between 12.60g
Furans mixed solution, 82 DEG C of isothermal reaction 2h.13.804g dimethyl dichlorosilane (DMCS) (0.12mol) and 30mL2- methyl tetrahydro is added dropwise
Furans, 45 DEG C of isothermal reaction 1h are warming up to 82 DEG C of isothermal reaction 2h.Other steps finally obtain dark brown viscous with embodiment 1
Shape resin.
1H-NMR result and FT-IR result are the same as embodiment 1.Resulting resin-soluble is in toluene.Program curing are as follows: 115
DEG C/1h, 130 DEG C/1h, 150 DEG C/2h, 170 DEG C/2h, 200 DEG C/2h.After resin solidification, the bulk for obtaining bright black densification is solid
Body.5% decomposition temperature of solidfied material is 575.7 DEG C, and 800 DEG C of residual rates are 86.7%.
Embodiment 4
13.248g magnesium powder (0.552mol) and 10mL2- methyltetrahydrofuran are added to four-hole boiling flask, are slowly added dropwise
55.134g bromoethane (0.506mol) and 10mL2- methyltetrahydrofuran.After dripping, 45 DEG C of isothermal reaction 2h.Slowly drop
Add tri- acetylenylbenzene of 1,3,5- (0.02mol) and 50mL2- methyl four of diacetylenic benzene (0.2mol) and 3.00g between 25.20g
Hydrogen furans mixed solution, 82 DEG C of isothermal reaction 2h.25.30g dimethyl dichlorosilane (DMCS) (0.22mol) and 30mL2- methyl tetrahydro is added dropwise
Furans, 45 DEG C of isothermal reaction 1h are warming up to 82 DEG C of isothermal reaction 2h.Other steps finally obtain brown color viscosity flow with embodiment 1
State resin.
1H-NMR result and FT-IR result are the same as embodiment 1.Resulting resin-soluble is in toluene.Program curing are as follows: 115
DEG C/1h, 130 DEG C/1h, 150 DEG C/2h, 170 DEG C/2h, 200 DEG C/2h.After resin solidification, the bulk for obtaining bright black densification is solid
Body.5% decomposition temperature of solidfied material is 684.4 DEG C, and 800 DEG C of residual rates are 92.7%.
The above, only presently preferred embodiments of the present invention, practical range not for the purpose of limiting the invention, Fan Yibenfa
Variation and modification carried out by shape described in bright claim, construction, feature and spirit should be included in right of the invention and want
It asks in range.
[bibliography]
[1]Itoh M.Anovel synthesis of a highly heat-resistant organosilicon
polymer using base catalysts[J].Catalysis Surveys from Japan.1999,3(1):61-69.
[2] synthesis and performance [J] petrochemical industry of the novel siliceous aryl polyyne resin of Yan Hao, Qi Huimin, Huang Farong
.2004,33(9):880-884.
[3] Jiang Huan, Deng Shifeng, Ruan Xiangzheng zinc chloride catalyze and synthesize siliceous aryne resin [J] polymer material science with
Engineering .2017,33 (11): 18-21,28.
Claims (8)
1. a kind of high-fire resistance silicon substrate benzyne resin of low-temperature setting, which is characterized in that the high-fire resistance resin has as follows
Structure, the former is the product structure formula that 1,3,5- tri- acetylenylbenzenes and dimethyl dichlorosilane (DMCS) react or the latter is a diethyl
The product structure formula that the mixture of tri- acetylenylbenzene of alkynyl benzene and 1,3,5- is copolymerized with dimethyl dichlorosilane (DMCS):
Or
2. a kind of preparation method of the high-fire resistance silicon substrate benzyne resin of low-temperature setting described in claim 1, which is characterized in that its
Key step are as follows:
(1) under inert gas protection, ethylmagnesium bromide Grignard Reagent is generated by the reaction of magnesium powder and bromoethane;
(2) above-mentioned reaction product and diacetylenic benzene and 1, the reaction of 3,5- tri- acetylenylbenzenes, generate acetenyl magnesium bromide;
(3) above-mentioned reaction product is reacted with chlorosilane, generates the polyyne base silicon substrate benzene resin that both ends are acetenyl sealing end.
3. the preparation method of the high-fire resistance silicon substrate benzyne resin of low-temperature setting according to claim 2, it is characterised in that: contain
The molar ratio of alkynyl class monomer and dimethyl dichlorosilane (DMCS) is 1:0.5~1, the molar ratio of diethynylbenzene and tri- ethynylbenzene of 1,3,5-
For 0:1,2:1,5:1,10:1.
4. the preparation method of the high-fire resistance silicon substrate benzyne resin of low-temperature setting according to claim 2, it is characterised in that: bromine
The molar ratio of alkynyl is 1.1:1 in ethane and acetylenic monomer, and the molar ratio of alkynyl is 1.0-1.3:1 in magnesium powder and acetylenic monomer.
5. the preparation method of the high-fire resistance silicon substrate benzyne resin of low-temperature setting according to claim 2, it is characterised in that: logical
The input ratio of alkynyl class monomer and silane is overregulated, molecular resin chain length is adjusted, controlling in polymer may participate in curing reaction
The content of silicon in the density of functional group, structure.
6. the preparation method of the high-fire resistance silicon substrate benzyne resin of low-temperature setting according to claim 2, it is characterised in that: close
Tetrahydrofuran, 2- methyltetrahydrofuran, toluene are generally at solvent used in alkynes Grignard Reagent.
7. described in the high-fire resistance silicon substrate benzyne resin or claim any one of 2-6 of low-temperature setting described in a kind of claim 1
Preparation method made from low-temperature setting high-fire resistance silicon substrate benzyne resin, preparing high-performance composite materials matrix, resistance to height
Application on warm coating and photoelectric material.
8. described in the high-fire resistance silicon substrate benzyne resin or claim any one of 2-6 of low-temperature setting described in a kind of claim 1
Preparation method made from low-temperature setting high-fire resistance silicon substrate benzyne resin, can be answered in spacecraft and field of photovoltaic materials
With.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910625516.8A CN110423350B (en) | 2019-07-11 | 2019-07-11 | Low-temperature cured high-heat-resistance silicon-based phenylalkyne resin and preparation method and application thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910625516.8A CN110423350B (en) | 2019-07-11 | 2019-07-11 | Low-temperature cured high-heat-resistance silicon-based phenylalkyne resin and preparation method and application thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
CN110423350A true CN110423350A (en) | 2019-11-08 |
CN110423350B CN110423350B (en) | 2022-07-01 |
Family
ID=68409233
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201910625516.8A Active CN110423350B (en) | 2019-07-11 | 2019-07-11 | Low-temperature cured high-heat-resistance silicon-based phenylalkyne resin and preparation method and application thereof |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN110423350B (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111333844A (en) * | 2020-01-06 | 2020-06-26 | 华东理工大学 | Preparation method of high-heat-resistance silicon oxide alkyne hybrid resin |
CN113354821A (en) * | 2020-03-06 | 2021-09-07 | 华东理工大学 | High-modulus silicon-containing aryne resin, composite material and preparation method thereof |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1355974A1 (en) * | 2000-11-10 | 2003-10-29 | Commissariat A L'Energie Atomique | Poly (ethynylene phenylene ethynylene polysiloxene (silylene)) and methods for preparing same |
JP2005012138A (en) * | 2003-06-23 | 2005-01-13 | Mitsui Chemicals Inc | High purity metal diffusion barrier film |
CN1709928A (en) * | 2005-07-05 | 2005-12-21 | 华东理工大学 | Aryne resin containing silicone |
CN102585240A (en) * | 2012-02-28 | 2012-07-18 | 华东理工大学 | Aryne resin containing boron and silicon and preparation method thereof |
CN108752374A (en) * | 2018-04-28 | 2018-11-06 | 华东理工大学 | Siliceous aryl propargyl ether resin and its synthesis, ternary resin and its preparation, composite material and its preparation of ethynyl phenyl sealing end |
-
2019
- 2019-07-11 CN CN201910625516.8A patent/CN110423350B/en active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1355974A1 (en) * | 2000-11-10 | 2003-10-29 | Commissariat A L'Energie Atomique | Poly (ethynylene phenylene ethynylene polysiloxene (silylene)) and methods for preparing same |
JP2005012138A (en) * | 2003-06-23 | 2005-01-13 | Mitsui Chemicals Inc | High purity metal diffusion barrier film |
CN1709928A (en) * | 2005-07-05 | 2005-12-21 | 华东理工大学 | Aryne resin containing silicone |
CN102585240A (en) * | 2012-02-28 | 2012-07-18 | 华东理工大学 | Aryne resin containing boron and silicon and preparation method thereof |
CN108752374A (en) * | 2018-04-28 | 2018-11-06 | 华东理工大学 | Siliceous aryl propargyl ether resin and its synthesis, ternary resin and its preparation, composite material and its preparation of ethynyl phenyl sealing end |
Non-Patent Citations (2)
Title |
---|
FAN WANG,等: "Synthesis and Characterization of Poly(dimethylsilylene ethynylenephenyleneethynylene) Terminated with Phenylacetylene", 《POLYMER BULLETIN》 * |
张玲玲,等: "含硅氢基团甲基芳炔树脂的合成及表征", 《过程工程学报》 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111333844A (en) * | 2020-01-06 | 2020-06-26 | 华东理工大学 | Preparation method of high-heat-resistance silicon oxide alkyne hybrid resin |
CN111333844B (en) * | 2020-01-06 | 2022-08-09 | 华东理工大学 | Preparation method of high-heat-resistance silicon oxide alkyne hybrid resin |
CN113354821A (en) * | 2020-03-06 | 2021-09-07 | 华东理工大学 | High-modulus silicon-containing aryne resin, composite material and preparation method thereof |
CN113354821B (en) * | 2020-03-06 | 2023-11-14 | 华东理工大学 | High-modulus silicon-containing aryne resin, composite material and preparation method thereof |
Also Published As
Publication number | Publication date |
---|---|
CN110423350B (en) | 2022-07-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN110423350A (en) | A kind of high-fire resistance silicon substrate benzyne resin of low-temperature setting and its preparation method and application | |
EP0745614B1 (en) | Synthesis of siloxane-functional telechelic hydrocarbon polymers | |
CN102585239B (en) | Novel high temperature resistant phenylboronic acid-siloxane-imino linear polymer and preparation method thereof | |
CN109369918A (en) | A kind of high boron content Si-B-C-N presoma and preparation method thereof | |
KR20140024244A (en) | Hydrosilicone resin and preparation process thereof | |
CN105968366A (en) | Liquid borosilicate resin and preparation method and application thereof | |
CN101875727B (en) | Method for preparing carborane-siloxane polymer under catalysis of Lewis acid | |
CN110423352B (en) | Preparation method of high-temperature-resistant organic silicon material containing carborane structure | |
CN106957433B (en) | Photo/thermal double-crosslinking hyperbranched polycarbosilane benzocyclobutene resin and preparation method thereof | |
CN111333844B (en) | Preparation method of high-heat-resistance silicon oxide alkyne hybrid resin | |
CN100497407C (en) | Aryne resin containing silicone | |
CN102234375B (en) | Polyphenylacetylene silicon oxide borane and preparation method thereof | |
CN102226000B (en) | Novel boron silicon alkyne hybrid high temperature resistant resin and preparation method thereof | |
CN108707234A (en) | A kind of silicon boron azane ceramic forerunner polymer containing borazine, preparation method and applications | |
CN101134816A (en) | Sesquialter siloxane polyaryne hybrid resin and preparation method and use thereof | |
CN101381463B (en) | Polymer with backbone chain having silicon-aromatic bispropargyl ether structure and preparation method thereof | |
CN101139442B (en) | Organic-inorganic hybrid resin containing sesquialter siloxane and preparation method and use thereof | |
CN115368572A (en) | Synthetic method of fluorine-containing temperature-resistant silicone resin | |
CN102010510A (en) | Novel high-temperature resistant phenylacetylene terminated poly (acetenyl-silane) and preparation method thereof | |
CN101709062A (en) | Novel silazane-diacetylene aniline silane and preparation method thereof | |
CN101693766B (en) | Hyper-branched silicon-contained aryne polymer and preparation method thereof | |
CN114573821B (en) | Liquid hyperbranched polycarbosilane, preparation method and application thereof | |
CN103319520B (en) | The preparation method of many benzocyclobutenes functionalized silane and resin thereof | |
CN113336951B (en) | Borosilicate-acetylene hybrid copolymer resin, cured product, and preparation method and application thereof | |
CN109722033B (en) | Preparation method of dianthranyl diphenyl ether vinyl silicone rubber |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |