CN109942819A - A kind of preparation method of straight chain ladder-like poly-phenyl silsesquioxane - Google Patents
A kind of preparation method of straight chain ladder-like poly-phenyl silsesquioxane Download PDFInfo
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Abstract
The invention belongs to technical field of organic synthesis, the present invention provides a kind of preparation methods of straight chain ladder-like poly-phenyl silsesquioxane, the following steps are included: phenyl silane and organic solvent are mixed, under the action of catalyst, polycondensation reaction occurs under the conditions of 40~80 DEG C, obtains straight chain ladder-like poly-phenyl silsesquioxane.In the present invention, phenyl silane hydrolyzes to form silanol under the catalytic action of catalyst, then the intermolecular polycondensation of silanol, forms straight chain ladder-like poly-phenyl silsesquioxane.The present invention only needs single step reaction that straight chain ladder-like poly-phenyl silsesquioxane can be obtained, and synthetic method is easier, and synthetic reaction condition is mild, reproducible, and yield is higher, and the period is short, is suitble to industrialized production.
Description
Technical field
The present invention relates to technical field of organic synthesis, and in particular to a kind of preparation of straight chain ladder-like poly-phenyl silsesquioxane
Method.
Background technique
Polyorganosilsesquioande (PSQ) refers to that molecular formula is (RSiO1.5)nPolysiloxanes, side chain " R " indicate and silicon
The connected various organic groups of atom, such as hydrogen, alkyl, aromatic radical, alkylene or other organic substituent groups.PSQ has reason
Mechanical performance, heat resistance and the electric property thought cause the great research interest of people, wherein polyphenylene silicon sesquialter oxygen
Alkane (PPSQ), especially trapezoidal PPSQ, structural formula are (C6H5SiO1.5)n, there is higher heat resistance, weatherability, chemically-resistant
Property, heatproof oxidation performance, electrical insulating property, optical transparence, waterproofness and anti-flammability, have a extensive future, can be widely applied to
The fields such as polymer modification, heat-insulating material, dielectric materials, coated coating and gas separation membrane.
Since the sixties in last century, Brown etc. has been put forward for the first time the preparation side of trapezium structure poly-phenyl silsesquioxane
Method, the hydrolysate of phenyl trichlorosilane is dissolved in toluene by they with high concentration (80~90%), and then at high temperature (250
DEG C) reflux 16h, obtained with stereoregularity ladderlike polymer PPSQ (Brown JF, Vogt J H, KatchmanA,
Et al.Double-chainpolymers of phenylsilsesquioxane.JAm Chem Soc, 1960,82:6194-
6195), but since its reaction temperature is higher and specific reaction mechanism reason, the trapezium structure synthesized by them is once by matter
It doubts；Late 1980s, Zhang Rongben etc. have been synthesized a series of with different side groups (hydrogen, benzene using " gradually coupling polymerization method "
Base, methyl, amino and photolytic activity base etc.) trapezoidal Polyorganosilsesquioande, but the phase needs using institute this method before the synthesis
" template molecule " organic diamine of meaning, complex synthetic route, higher cost (Yang J, Bai F, Zhang R, et
al.Temperature dependence of the fluorescence spectra of ladderlike
polyphenylsilsesquioxane and ladderlike 1,4-phenylene-bridged
Polyvinylsiloxane.Chinese J Polym Sci, 2002,20:15-23)；In Chinese patent CN201010190169
And Inorg.Chem.2018, the synthesis of the phenyl polysilsesquioxane with ring trapezium structure is reported in 57,3883 documents
Preparation method, but this method is complex and yield is relatively low, and synthesis cycle is long, somewhat expensive.
Summary of the invention
The purpose of the present invention is to provide a kind of preparation methods of straight chain ladder-like poly-phenyl silsesquioxane, using the present invention
The preparation method of offer can obtain that regularity is good and high performance poly-phenyl silsesquioxane, and preparation process is easy, reaction
Mild condition.
In order to achieve the above-mentioned object of the invention, the present invention the following technical schemes are provided:
The present invention provides a kind of preparation methods of straight chain ladder-like poly-phenyl silsesquioxane, comprising the following steps: by benzene
Base silane and organic solvent mixing occur polycondensation reaction, obtain straight chain trapezoidal polyphenyl base silicon sesquialter oxygen under the action of catalyst
Alkane；The temperature of the polycondensation reaction is 40~80 DEG C；
The straight chain ladder-like poly-phenyl silsesquioxane has structure shown in formula I:
Wherein, n=10~30.
Preferably, the amount ratio of the phenyl silane and organic solvent is 1g:5~20mL.
Preferably, the mass ratio of the phenyl silane and catalyst is 1:(0.004~0.1).
Preferably, the phenyl silane is preferably phenyl trichlorosilane, phenyltrimethoxysila,e or phenyl triethoxy
Silane；The organic solvent includes acetone, petroleum ether, acetonitrile, methylene chloride, chloroform, tetrahydrofuran, pyridine and dioxy six
One or more of ring.
Preferably, the catalyst include potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate, tetramethylammonium hydroxide and
One or more of tetraethyl ammonium hydroxide.
Preferably, the mixing carries out under agitation, and the speed of the stirring is 80~200rpm.
Preferably, the catalyst is added drop-wise to the mixed liquor of phenyl silane and organic solvent in the form of catalyst aqueous solution
In, the concentration of the catalyst aqueous solution is 0.005~0.02g/mL.
Preferably, the speed of the dropwise addition is 2~10mL/min.
Preferably, the time of the polycondensation reaction is 12~72h.
It preferably, further include precipitating, separation of solid and liquid, washing and drying after the completion of the polycondensation reaction.
The present invention provides a kind of preparation methods of straight chain ladder-like poly-phenyl silsesquioxane, comprising the following steps: by benzene
Base silane and organic solvent mixing, keep its evenly dispersed, under the action of catalyst, polycondensation reaction occur under the conditions of 40~80 DEG C,
Obtain straight chain ladder-like poly-phenyl silsesquioxane.In the present invention, phenyl silane hydrolyzes to form under the catalytic action of catalyst
Silanol, the then intermolecular polycondensation of silanol form straight chain ladder-like poly-phenyl silsesquioxane.The present invention only needs single step reaction
Straight chain ladder-like poly-phenyl silsesquioxane is obtained, compared with the prior art, synthetic method is easier, and uses organic molten
Agent boiling point is lower, and the poly-phenyl silsesquioxane derivative of high regularity can be obtained under mild reaction conditions, repeatability
Good, yield is higher, and the period is short, is suitble to industrialized production.Shown by the test result of embodiment using preparation provided by the invention
The straight chain ladder-like poly-phenyl silsesquioxane structural stability that method obtains is good, and yield is 96.2~98.3%；Products therefrom two
End is silicone hydroxyl, and the trapezium structure with high regularity can be by carrying out further reaction to silicone hydroxyl therein to prepare
The poly-phenyl silsesquioxane derivative of a variety of groups containing different function.
Detailed description of the invention
Fig. 1 is the FT-IR spectrogram of straight chain ladder-like poly-phenyl silsesquioxane prepared by embodiment 1；
Fig. 2 is straight chain ladder-like poly-phenyl silsesquioxane prepared by embodiment 11H NMR spectra；
Fig. 3 is the XRD spectra of straight chain ladder-like poly-phenyl silsesquioxane prepared by embodiment 1；
Fig. 4 is the MALDI-TOF MS spectrogram of straight chain ladder-like poly-phenyl silsesquioxane prepared by embodiment 1；
Fig. 5 is the TG spectrogram of straight chain ladder-like poly-phenyl silsesquioxane prepared by embodiment 1.
Specific embodiment
The present invention provides a kind of preparation methods of straight chain ladder-like poly-phenyl silsesquioxane, comprising the following steps: by benzene
Base silane and organic solvent mixing occur polycondensation reaction, obtain straight chain trapezoidal polyphenyl base silicon sesquialter oxygen under the action of catalyst
Alkane；The temperature of the polycondensation reaction is 40~80 DEG C；
The straight chain ladder-like poly-phenyl silsesquioxane has structure shown in formula I:
Wherein, n=10~30.
In the present invention, if without specified otherwise, all raw material components are commercially available quotient well known to those skilled in the art
Product.
In the present invention, the amount ratio of the phenyl silane and organic solvent is preferably 1g:5~20mL；The phenyl silicon
The mass ratio of alkane and catalyst is preferably 1:(0.004~0.1), more preferably 1:(0.008~0.02).The present invention is by phenyl silicon
The amount ratio of alkane, organic solvent and catalyst is limited to above range, is conducive to the rule for improving ladder-like poly-phenyl silsesquioxane
Whole degree, while also can be improved the yield of straight chain ladder-like poly-phenyl silsesquioxane.
In the present invention, the phenyl silane is preferably three second of phenyl trichlorosilane, phenyltrimethoxysila,e or phenyl
Oxysilane.In the present invention, the organic solvent preferably includes acetone, petroleum ether, acetonitrile, methylene chloride, chloroform, four
One or more of hydrogen furans, pyridine and dioxane, more preferably pyridine, methylene chloride, tetrahydrofuran or acetonitrile.
In the present invention, the mixing of the phenyl silane and organic solvent preferably carries out under agitation, the stirring
Speed be preferably 80~200rpm, more preferably 100~150rpm.The present invention does not have special limit to the time of the stirring
Fixed, being uniformly mixed with phenyl silane with organic solvent is advisable.
In the present invention, the catalyst preferably includes potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate, tetramethyl hydrogen
One or more of amine-oxides and tetraethyl ammonium hydroxide, more preferably potassium hydroxide, tetraethyl ammonium hydroxide, tetramethyl hydrogen
Amine-oxides, potassium carbonate or sodium hydroxide.In the present invention, the catalyst can promote phenyl silane to hydrolyze to form silanol, into
And polycondensation obtains straight chain ladder-like poly-phenyl silsesquioxane, can shorten reaction time.
In the present invention, the catalyst is preferably added drop-wise to phenyl silane and organic solvent in the form of catalyst aqueous solution
Mixed liquor in, the concentration of the catalyst aqueous solution is preferably 0.005~0.02g/mL, more preferably 0.01~0.02g/
mL；The water is preferably distilled water or deionized water；The speed of the dropwise addition is preferably 2~10mL/min, more preferably 5~
10mL/min.The present invention will be in catalyst addition system by the way of being added dropwise, it is therefore an objective to keep hydrolysis uniform and stable
It carries out.
In the present invention, the temperature of the polycondensation reaction is preferably 40~80 DEG C, and more preferably 60~80 DEG C；The polycondensation
The time of reaction is preferably 12~72h, more preferably 24~48h, and the time of the polycondensation reaction is added dropwise out with catalyst
Beginning timing.
It in the present invention, further include precipitating, separation of solid and liquid, washing and drying after the completion of the polycondensation reaction.In the present invention
In, the precipitating is particularly preferred as pouring into reaction solution obtained by polycondensation reaction in precipitating reagent and stir, and is then allowed to stand, obtaining upper layer is
Colourless transparent solution, the product system that lower layer is white precipitate.In the present invention, the precipitating reagent is preferably water, dehydrated alcohol
Or anhydrous methanol, the water are preferably distilled water or deionized water.In the present invention, reaction solution obtained by the polycondensation reaction and heavy
The volume ratio of shallow lake agent is preferably 1:(5~50), more preferably 1:(5~20).The present invention promotes straight chain trapezoidal poly- using precipitating reagent
The precipitation of phenylsilsesquioxane.
In the present invention, the speed of the stirring is preferably 200~1000rpm when precipitating product, more preferably 500~
1000rpm；The time of the stirring is preferably 1~10h, more preferably 2~4h；The time of the standing is preferably 8~for 24 hours,
More preferably 8~12h.In the present invention, after the completion of the precipitating, products therefrom system is preferably carried out solid-liquid point by the present invention
From, washing and dry, straight chain ladder-like poly-phenyl silsesquioxane is obtained.In the present invention, the mode of the separation of solid and liquid is preferred
For vacuum filtration, the present invention does not require the vacuum degree of the vacuum filtration, is advisable with realizing to be separated by solid-liquid separation.In the present invention
In, the washing is particularly preferred as being washed repeatedly with water and dehydrated alcohol, and the water is preferably distilled water；The number of the washing
Preferably 3 times.In the present invention, the drying preferably carries out under vacuum conditions, and the temperature of the drying is preferably 60~120
DEG C, more preferably 80~100 DEG C；The time of the drying is preferably 8~for 24 hours, more preferably 10h.
In the present invention, the straight chain ladder-like poly-phenyl silsesquioxane is that both ends have hydroxyl, and centre is ordered ladder-like
Poly-phenyl silsesquioxane other function group can be further introduced into due to the hydroxyl with reactivity, obtain containing not
The poly-phenyl silsesquioxane derivative of congenerous group.
Below in conjunction with the embodiment in the present invention, the technical solution in the present invention is clearly and completely described.It is aobvious
So, described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.Based on the reality in the present invention
Example is applied, every other embodiment obtained by those of ordinary skill in the art without making creative efforts all belongs to
In the scope of protection of the invention.
Embodiment 1
(1) 19.84g phenyltrimethoxysila,e is added to reflux condensing tube, constant pressure funnel, temperature regulating device
In the 500mL three-necked flask of magnetic agitation, 300mL pyridine is added, stirs 20min under the speed of 100rpm, is warming up to 60
℃；Then 0.3g potassium hydroxide is dissolved in 30mL distilled water, obtains potassium hydroxide aqueous solution；Potassium hydroxide aqueous solution is delayed
Slowly it is added drop-wise in three-necked flask, time for adding 30min；12h is reacted after being added dropwise, and obtains shallow white reaction liquid；
(2) under agitation, the shallow white reaction liquid is poured into the dehydrated alcohol of 3L, in the speed of 600rpm
Lower stirring 30min, is then allowed to stand 1h, and obtaining upper layer is colourless transparent solution, and lower layer is the product system of white precipitate, this is produced
Objects system filters, and is washed three times repeatedly with distilled water and dehydrated alcohol, filtered product is placed in 60 DEG C of vacuum drying ovens and is done
Dry 10h obtains straight chain ladder-like poly-phenyl silsesquioxane, yield 97.3%.
Embodiment 2
(1) 21.16g phenyl trichlorosilane is added to reflux condensing tube, constant pressure funnel, temperature regulating device and magnetic
In the 500mL three-necked flask of power stirring, 100mL methylene chloride is added, stirs 10min under the speed of 160rpm, is warming up to 80
℃；Then 0.2g tetraethyl ammonium hydroxide is dissolved in 10mL distilled water, obtains tetraethyl ammonium hydroxide aqueous solution；By tetrem
Base ammonium hydroxide aqueous solution is slowly dropped in three-necked flask, time for adding 30min；It reacts for 24 hours, obtains shallow after being added dropwise
White reaction liquid；
(2) under agitation, the shallow white reaction liquid is poured into the anhydrous methanol of 2L, in the speed of 800rpm
Lower stirring 30min, is then allowed to stand 1h, and obtaining upper layer is colourless transparent solution, and lower layer is the product system of white precipitate, this is produced
Objects system filters, and is washed three times repeatedly with distilled water and dehydrated alcohol, filtered product is placed in 80 DEG C of vacuum drying ovens and is done
Dry 10h obtains straight chain ladder-like poly-phenyl silsesquioxane, yield 97.1%.
Embodiment 3
(1) 19.84g phenyltrimethoxysila,e is added to reflux condensing tube, constant pressure funnel, temperature regulating device
In the 500mL three-necked flask of magnetic agitation, 250mL tetrahydrofuran is added, 20min is stirred under the speed of 150rpm, heats up
To 70 DEG C；Then 0.08g tetramethylammonium hydroxide is dissolved in 10mL distilled water, obtains tetramethylammonium hydroxide aqueous solution；
Tetramethylammonium hydroxide aqueous solution is slowly dropped in three-necked flask, time for adding 30min；It is reacted after being added dropwise for 24 hours,
Obtain shallow white reaction liquid；
(2) under agitation, the shallow white reaction liquid is poured into the dehydrated alcohol of 2L, in the speed of 500rpm
Lower stirring 30min, is then allowed to stand 1h, and obtaining upper layer is colourless transparent solution, and lower layer is the product system of white precipitate, this is produced
Objects system filters, and is washed three times repeatedly with distilled water and dehydrated alcohol, filtered product is placed in 80 DEG C of vacuum drying ovens and is done
Dry 10h obtains straight chain ladder-like poly-phenyl silsesquioxane, yield 98.3%；
Embodiment 4
(1) 24.04g phenyl triethoxysilane is added to reflux condensing tube, constant pressure funnel, temperature regulating device
In the 500mL three-necked flask of magnetic agitation, 200mL acetonitrile is added, stirs 10min under the speed of 200rpm, is warming up to 60
℃；Then 0.2g potassium carbonate is dissolved in 10mL distilled water, obtains wet chemical；Wet chemical is slowly added dropwise
Into three-necked flask, time for adding 30min；It is reacted after being added dropwise for 24 hours, obtains shallow white reaction liquid；
(2) under agitation, the shallow white reaction liquid is poured into the anhydrous methanol of 1.5L, in the speed of 800rpm
Degree is lower to stir 30min, is then allowed to stand 1h, obtaining upper layer is colourless transparent solution, and lower layer is the product system of white precipitate, by this
Product system filters, and is washed three times repeatedly with distilled water and dehydrated alcohol, filtered product is placed in 80 DEG C of vacuum drying ovens
Dry 10h, obtains straight chain ladder-like poly-phenyl silsesquioxane, yield 95.5%.
Embodiment 5
(1) 24.04g phenyl triethoxysilane is added to reflux condensing tube, constant pressure funnel, temperature regulating device
In the 500mL three-necked flask of magnetic agitation, 200mL chloroform is added, 20min is stirred under the speed of 160rpm, heats up
To 80 DEG C；Then 0.2g sodium hydroxide is dissolved in 10mL distilled water, obtains sodium hydrate aqueous solution；Sodium hydroxide is water-soluble
Liquid is slowly dropped in three-necked flask, time for adding 30min；48h is reacted after being added dropwise, and obtains shallow white reaction liquid；
(2) under agitation, the shallow white reaction liquid is poured into the dehydrated alcohol of 5L, in the speed of 100rpm
Lower stirring 30min, is then allowed to stand 1h, and obtaining upper layer is colourless transparent solution, and lower layer is the product system of white precipitate, this is produced
Objects system filters, and is washed three times repeatedly with distilled water and dehydrated alcohol, filtered product is placed in 100 DEG C of vacuum drying ovens and is done
Dry 10h obtains straight chain ladder-like poly-phenyl silsesquioxane, yield about 96.2%.
Test example
Structural characterization and performance detection, acquired results are carried out to 1 gained straight chain ladder-like poly-phenyl silsesquioxane of embodiment
See Fig. 1~5.
FT-IR spectrogram is as shown in Figure 1, in 3072,3050,3014cm-1Absorption peak be the flexible vibration of C-H on aromatic rings
It is dynamic, in 1593,1433cm-1Absorption peak be aromatic rings on C-C stretching vibration, 724cm-1Place is C-H plain bending on aromatic rings
Vibration, 691cm-1Locate the plane internal deformation that absorption peak is phenyl ring C-C to vibrate, and in 1100cm-1And 1024cm-1Two suctions at place
The absorption peak that peak is Si-O-Si stretching vibration is received, in addition, in 3620cm-1Nearby there is the absorption peak of Si-OH, this proves to be made
Product be both ends have silicone hydroxyl high regularity ladder-like poly-phenyl silsesquioxane.
1HNMR spectrogram is as shown in Fig. 2, the packet peak in Fig. 2 at 6.5~8ppm corresponds to H, 5.58ppm in product on phenyl ring
Correspond to the chemical shift of H on product Si-OH.
XRD spectra is as shown in figure 3, there are two 2 θ=7.3 ° of apparent diffraction maximum and 2 θ=19.3 ° in Fig. 3, at 7.3 °
Diffraction maximum be apparent spike, the diffraction maximum at 19.3 ° is disperse peak；The spike of small angular region corresponds to 2 of ladder polymer
Width between main chainAnother corresponds to the thickness of ladder polymer compared with the peak of disperseIllustrate to produce
Object is for trapezium structure；In addition, peak at 7.3 ° is sharper, relative intensity is bigger, it is meant that trapezium structure regularity is higher.From figure
3 can see, and the spike intensity of the small angular region of product is obviously more much higher than the disperse peak intensity of big angular region, shows its trapezoidal skeleton
It is more complete, regularity is high, this is consistent with FTIR characterization result.
MALDI-TOF spectrogram as shown in figure 4, straight chain ladder-like poly-phenyl silsesquioxane synthesized by the present invention MAIDI-
The matrix of TOF contains a certain amount of sodium salt, can generate [M+Na]+Adduct ion, the knot of straight chain ladder-like poly-phenyl silsesquioxane
Structure formula is (Ph2Si2O3)nO2H4, repetitive unit Ph2Si2O3, relative molecular mass 258, therefore its molecular weight should be
n*258+36。
TG spectrogram as shown in figure 5, as seen from Figure 5, the thermal stability of straight chain ladder-like poly-phenyl silsesquioxane is very high,
Temperature of initial decomposition is about 473 DEG C, and the carbon left at 900 DEG C is 74.39%.
Straight chain trapezoidal polyphenyl base silicon sesquialter is prepared using method provided by the invention it can be seen from embodiment testing result
Oxygen alkane yield with higher, yield are 96.2~98.3%；And gained straight chain ladder-like poly-phenyl silsesquioxane has high rule
The trapezium structure of whole degree, product both ends are silicone hydroxyl, and structural stability is good, and have excellent thermal stability.
The above is only a preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
For member, various improvements and modifications may be made without departing from the principle of the present invention, these improvements and modifications are also answered
It is considered as protection scope of the present invention.
Claims (10)
1. a kind of preparation method of straight chain ladder-like poly-phenyl silsesquioxane, which comprises the following steps:
Phenyl silane and organic solvent are mixed, under the action of catalyst, polycondensation reaction occurs, obtains straight chain trapezoidal polyphenyl base silicon
Sesquioxyalkane；The temperature of the polycondensation reaction is 40~80 DEG C；
The straight chain ladder-like poly-phenyl silsesquioxane has structure shown in formula I:
Wherein, n=10~30.
2. preparation method according to claim 1, which is characterized in that the amount ratio of the phenyl silane and organic solvent is
1g:5~20mL.
3. preparation method according to claim 1, which is characterized in that the mass ratio of the phenyl silane and catalyst is 1:
(0.004~0.1).
4. preparation method according to claim 1, which is characterized in that the phenyl silane is phenyl trichlorosilane, phenyl
Trimethoxy silane or phenyl triethoxysilane；The organic solvent includes acetone, petroleum ether, acetonitrile, methylene chloride, trichlorine
One or more of methane, tetrahydrofuran, pyridine and dioxane.
5. preparation method according to claim 1, which is characterized in that the catalyst include potassium hydroxide, sodium hydroxide,
One or more of potassium carbonate, sodium carbonate, tetramethylammonium hydroxide and tetraethyl ammonium hydroxide.
6. preparation method according to claim 1, which is characterized in that the mixing carries out under agitation, described to stir
The speed mixed is 80~200rpm.
7. preparation method according to claim 1, which is characterized in that the catalyst is dripped in the form of catalyst aqueous solution
It is added in the mixed liquor of phenyl silane and organic solvent, the concentration of the catalyst aqueous solution is 0.005~0.02g/mL.
8. preparation method according to claim 7, which is characterized in that the speed of the dropwise addition is 2~10mL/min.
9. preparation method according to claim 1, which is characterized in that the time of the polycondensation reaction is 12~72h.
10. preparation method according to claim 1, which is characterized in that further include precipitating after the completion of the polycondensation reaction, solid
Liquid separation, washing and drying.
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Cited By (4)
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| CN110499004A (en) * | 2019-08-30 | 2019-11-26 | 北京理工大学 | While a kind of trapezoidal POSS modified ethenyl resin and preparation method thereof containing phenyl and vinyl |
| CN114031779A (en) * | 2021-11-01 | 2022-02-11 | 兰州瑞朴科技有限公司 | Phosphorus-containing ladder-shaped polysiloxane, preparation method thereof and application of phosphorus-containing ladder-shaped polysiloxane as flame-retardant synergist |
| CN114805812A (en) * | 2022-04-07 | 2022-07-29 | 苏州大学 | Trapezoidal phenyl polysilsesquioxane/polycaprolactone/trapezoidal phenyl polysilsesquioxane blend membrane and preparation method thereof |
| CN115058011A (en) * | 2022-06-21 | 2022-09-16 | 北京理工大学 | Porous polyphenyl silsesquioxane, and preparation method and application thereof |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110499004A (en) * | 2019-08-30 | 2019-11-26 | 北京理工大学 | While a kind of trapezoidal POSS modified ethenyl resin and preparation method thereof containing phenyl and vinyl |
| CN114031779A (en) * | 2021-11-01 | 2022-02-11 | 兰州瑞朴科技有限公司 | Phosphorus-containing ladder-shaped polysiloxane, preparation method thereof and application of phosphorus-containing ladder-shaped polysiloxane as flame-retardant synergist |
| CN114031779B (en) * | 2021-11-01 | 2023-02-28 | 兰州瑞朴科技有限公司 | Phosphorus-containing ladder-shaped polysiloxane, preparation method thereof and application of phosphorus-containing ladder-shaped polysiloxane as flame-retardant synergist |
| CN114805812A (en) * | 2022-04-07 | 2022-07-29 | 苏州大学 | Trapezoidal phenyl polysilsesquioxane/polycaprolactone/trapezoidal phenyl polysilsesquioxane blend membrane and preparation method thereof |
| CN115058011A (en) * | 2022-06-21 | 2022-09-16 | 北京理工大学 | Porous polyphenyl silsesquioxane, and preparation method and application thereof |
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