CN110452385A - A kind of incomplete polycondensation cage type phenyl silsesquioxane of alkali metal containing sodium and preparation method thereof - Google Patents
A kind of incomplete polycondensation cage type phenyl silsesquioxane of alkali metal containing sodium and preparation method thereof Download PDFInfo
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Abstract
The present invention provides incomplete polycondensation cage type phenyl silsesquioxanes of a kind of alkali metal containing sodium and preparation method thereof, belong to metal-hybrid inorganic-organic materials technical field.The incomplete polycondensation cage type phenyl silsesquioxane thermal stability of alkali metal containing sodium provided by the invention is high, its gathered around under conditions of keeping cage structure there are three with high reaction activity group, respectively two Si-OH and Si-ONa further can react to obtain the POSS derivative of more multifunction by sealing angle.Preparation method provided by the invention is easy to operate simultaneously, and synthesis cycle is short, and yield is high, reproducible, is suitble to industrial mass production.
Description
Technical field
The present invention relates to metal-hybrid inorganic-organic materials technical field, in particular to a kind of alkali metal containing sodium it is endless
Full reduced poly- cage type phenyl silsesquioxane and preparation method thereof.
Background technique
Incomplete polycondensation cage type phenyl silsesquioxane has incomplete polycondensation cagelike structure and multiple active groups, kind
Class, number are various, and have regular structure, nano-scale, excellent compatibility and modifiability, become molecule knot
Good selection in structure design and material modification, is one of the hot spot of current organic-inorganic materials science field research.
Due to there is the presence of metallic element to impart its certain special property in metallasesquioxanes, especially it is being catalyzed
Utilization in terms of agent, however metallasesquioxanes at this stage are the sesquialter silicon containing Si-OH with incomplete polycondensation mostly
Oxygen alkane is prepared as raw material, and it is expensive, and yield is lower, and Si-OH is more unstable, is easy autohemagglutination, this gives metal sesquialter
The application of siloxanes brings very big limitation.And due to the incomplete polycondensation cage type phenyl silsesquioxane of alkali metal containing have compared with
Strong reactivity and higher mutability, these features make its more difficult synthesis and separation.
Summary of the invention
In view of this, it is an object of that present invention to provide a kind of incomplete polycondensation cage type phenyl silsesquioxanes of alkali metal containing sodium
Alkane and preparation method thereof.The incomplete polycondensation cage type phenyl silsesquioxane reactivity of alkali metal containing sodium provided by the invention
Height, thermal stability is high, and structural stability is good, and preparation method is easy to operate, and synthesis cycle is short, and yield is high.
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 incomplete polycondensation cage type phenyl silsesquioxanes of alkali metal containing sodium, have shown in Formulas I
Structure:
The present invention provides the preparation method of the incomplete polycondensation cage type phenyl silsesquioxane of above-mentioned alkali metal containing sodium, packets
Include following steps:
Phenyl trialkoxysilane, the alkaline matter containing metallic sodium, organic solvent and water are mixed, it is anti-to carry out cyclic polycondensation
It answers, obtains the incomplete polycondensation cage type phenyl silsesquioxane of alkali metal containing sodium.
Preferably, the phenyl trialkoxysilane is phenyltrimethoxysila,e and/or phenyl triethoxysilane.
Preferably, the alkaline matter containing metallic sodium is one or more of sodium hydroxide, sodium ethoxide and sodium methoxide.
Preferably, the organic solvent is tetrahydrofuran, methanol, ethyl alcohol, acetone, isopropanol, chloroform, methylene chloride, first
One or more of benzene and benzene.
Preferably, the molar ratio of the phenyl trialkoxysilane, the alkaline matter containing metallic sodium and water is (0.5~1):
(0.4~0.7): (0.8~1.8).
Preferably, the amount ratio of the phenyl trialkoxysilane and organic solvent is (0.8~1) g:(1.5~7) mL.
Preferably, the temperature of the cyclic polycondensation reaction is 55~70 DEG C, the time is 12~for 24 hours.
It preferably, further include being post-processed to the cyclic polycondensation reaction liquid, after described after the cyclic polycondensation reaction
Processing the following steps are included:
The cyclic polycondensation reaction liquid is successively filtered, washed and dried, the endless full reduced of alkali metal containing sodium is obtained
Poly- cage type phenyl silsesquioxane solid.
Preferably, the temperature of the drying is 180~200 DEG C.
The present invention provides a kind of incomplete polycondensation cage type phenyl silsesquioxanes of alkali metal containing sodium, have shown in Formulas I
Structure.The incomplete polycondensation cage type phenyl silsesquioxane of alkali metal containing sodium provided by the invention is in the item for keeping cage structure
It is gathered around under part there are three the group with high reaction activity, respectively two Si-OH and Si-ONa can further pass through envelope
React to obtain cage modle polysilsesquioxane (POSS) derivative of more multifunction in angle；Alkali metal containing sodium provided by the invention simultaneously
Incomplete polycondensation cage type phenyl silsesquioxane thermal stability it is high.Embodiment the result shows that, alkali metal containing provided by the invention
The incomplete polycondensation cage type phenyl silsesquioxane of sodium T in thermogravimetric analysis95%It is 386.4 DEG C, 800 DEG C of carbon lefts are
72.18%, there is very high thermal stability.
The present invention provides the preparation method of the incomplete polycondensation cage type phenyl silsesquioxane of above-mentioned alkali metal containing sodium, this
Method is easy to operate, and synthesis cycle is short, and yield is high, reproducible, is suitble to industrial mass production.
Detailed description of the invention
Fig. 1 is the FT-IR spectrogram of Na-Ph-POSS prepared by embodiment 1；
Fig. 2 is Na-Ph-POSS's prepared by embodiment 11H NMR spectra；
Fig. 3 is the MALDI-TOF-MS spectrogram of Na-Ph-POSS prepared by embodiment 1；
Fig. 4 is the TG spectrogram of Na-Ph-POSS prepared by embodiment 1.
Specific embodiment
The present invention provides a kind of incomplete polycondensation cage type phenyl silsesquioxanes of alkali metal containing sodium, have shown in Formulas I
Structure:
The incomplete polycondensation cage type phenyl silsesquioxane of alkali metal containing sodium provided by the invention is keeping cage structure
Under the conditions of gather around there are three the group with high reaction activity, respectively two Si-OH and Si-ONa can be used as presoma
Compound (such as more chlorine metallic compounds, polyvalent metal of (such as presoma of unfilled corner closed loop method) and many active functional groups
Alkoxide and alkoxy silane etc.) reaction, form POSS derivative.Meanwhile alkali metal containing sodium provided by the invention is endless full reduced
Poly- cage type phenyl silsesquioxane has good thermal stability high and structural stability.
The present invention provides the preparation method of the incomplete polycondensation cage type phenyl silsesquioxane of above-mentioned alkali metal containing sodium, packets
Include following steps:
Phenyl trialkoxysilane, the alkaline matter containing metallic sodium, organic solvent and water are mixed, it is anti-to carry out cyclic polycondensation
It answers, obtains the incomplete polycondensation cage type phenyl silsesquioxane of alkali metal containing sodium.
In the present invention, the phenyl trialkoxysilane is preferably three ethoxy of phenyltrimethoxysila,e and/or phenyl
Base silane；The alkaline matter containing metallic sodium is preferably one or more of sodium hydroxide, sodium ethoxide and sodium methoxide；It is described
Organic solvent be preferably one of tetrahydrofuran, methanol, ethyl alcohol, acetone, isopropanol, chloroform, methylene chloride, toluene and benzene or
It is several；The water is preferably distilled water, and in the present invention, the effect of the water is the alkoxy made in phenyl trialkoxysilane
Hydrolysis, and then promote cyclic polycondensation reaction.
The present invention preferably mixes under normal temperature conditions, and the mixed mode is preferably stirred, the stirring
Revolving speed be preferably 30~100r/min, more preferably 50~80r/min.In the present invention, the phenyl trialkoxysilane,
The molar ratio of alkaline matter and water containing metallic sodium is preferably (0.5~1): (0.4~0.7): (0.8~1.8), more preferably
(0.6~0.8): (0.5~0.6): (1~1.5)；The amount ratio of the phenyl trialkoxysilane and organic solvent is preferably
(0.8~1) g:(1.5~7) mL, more preferably 0.9g:(3~5) mL.
In the present invention, the temperature of the cyclic polycondensation reaction is preferably 55~70 DEG C, and more preferably 60~65 DEG C；It is described
The time of cyclic polycondensation reaction is preferably 12~for 24 hours, more preferably 18~20h.The present invention preferably carries out under stirring conditions
The cyclization polycondensation reaction, the revolving speed of the stirring is preferably 30~100r/min, more preferably 50~80r/min.
In the present invention, when the phenyl trialkoxysilane is phenyl triethoxysilane, the cyclization polycondensation is anti-
The reaction equation answered is as shown in formula a:
The present invention further preferably includes post-processing to the cyclic polycondensation reaction liquid after the cyclic polycondensation reaction,
The post-processing preferably includes following steps:
The cyclic polycondensation reaction liquid is successively filtered, washed and dried, the endless full reduced of alkali metal containing sodium is obtained
Poly- cage type phenyl silsesquioxane solid.
In the present invention, the filtering preferably filters；In the present invention, the washing with detergent preferably with it is described at
Organic solvent used is identical when ring polycondensation reaction, and the present invention does not have special requirement to the mode of the washing, uses this field
Mode of washing known to technical staff.In the present invention, the mode of the drying is preferably air blast drying, the drying
Temperature is preferably 180~200 DEG C；The present invention does not have special requirement to the time of the drying, can make the moisture in solid
It completely removes.
Preparation method of the present invention is from a wealth of sources using phenyl trialkoxysilane as starting material, at low cost；Reaction
Process is easy to operate, mild condition, reproducible, has the advantages that yield is high, synthesis cycle is short.
Below with reference to embodiment to the incomplete polycondensation cage type phenyl silsesquioxane of alkali metal containing sodium provided by the invention
And preparation method thereof be described in detail, but they cannot be interpreted as limiting the scope of the present invention.
Embodiment 1
100mL acetone is added in the three-necked flask with reflux condensing tube, temperature regulating device and magnetic stirring apparatus, In
2gNaOH, 1mL distilled water and 15.6g phenyl triethoxysilane are added under 30r/min stirring, is warming up to 55 DEG C, reaction
16h has white solid generation, forms suspension, suspension is filtered, and using a large amount of acetone washings, 180 DEG C of air blast are dried, most
The incomplete polycondensation cage type phenyl silsesquioxane (being denoted as Na-Ph-POSS) of alkali metal containing sodium is obtained afterwards, and yield is about
82.6%.
Examination of infrared spectrum is carried out to gained Na-Ph-POSS, gained spectrogram is as shown in Figure 1, gained spectral data are as follows: FT-
IR (KBr, cm-1): 3712,3676 (- ONa), 3050~3070 (C-H), 1714 (Ph), 1594 (Ph), 1429 (Ph), 1000~
1100(Si-O).In Fig. 1,3712cm-1And 3676cm-1For the absorption peak of sodium oxygen key, 3050~3070cm-1It is stretched for C-H on phenyl ring
Contracting vibration absorption peak, 1714cm-1, 1594cm-1And 1429cm-1For phenyl ring skeletal vibration absorption peak, 1000~1100cm-1It is Si-
O key chattering absorption peak.As seen from Figure 1, the incomplete polycondensation cage type phenyl silsesquioxane of present invention gained alkali metal containing sodium
Contain Si-OH and Si-ONa active group in alkane.
Nuclear magnetic resonance spectroscopy test is carried out to gained Na-Ph-POSS, gained spectrogram is as shown in Fig. 2, gained spectral data
For1HNMR(CDCl3, δ, ppm): 6.0~8.0 (Ph, Si-OH).In Fig. 2, on phenyl ring and in Si-OH at 6.0~8.0ppm
Hydrogen Proton signal peak.As shown in Figure 2, raw material phenyl triethoxysilane1Occur at 3.9ppm (a) in H NMR spectra-
CH2And-the CH occurred at 1.3ppm (b)3Hydrogen Proton signal peak disappear completely in the 1HNMR spectrogram of product Na-Ph-POSS
It loses, shows that phenyl triethoxysilane hydrolysis is complete.
MALDI-TOF-MS (Matrix Assisted Laser Desorption time-of-flight mass spectrometry) matter is carried out to gained Na-Ph-POSS
Spectrum analysis, acquired results are as shown in Figure 3.Only in 952.9 (Na-Ph-POSS+H in Fig. 3+) there is single peak, Er Qieyu
The theoretical molecular weight (952) of Na-Ph-POSS matches, and shows that products therefrom of the present invention is single.
Thermogravimetric analysis is carried out under nitrogen atmosphere to gained Na-Ph-POSS, gained TG spectrogram is as shown in Figure 4.Na- in Fig. 4
The T of Ph-POSS95%It is 386.4 DEG C, 800 DEG C of carbon lefts are 72.18%, show that it, with very high thermal stability, meets general
The processing request of polymer.
Embodiment 2
500mL ethyl alcohol is added to equipped with the three-necked flask with reflux condensing tube, temperature regulating device and magnetic stirring apparatus
In, 7g sodium ethoxide, 8mL distilled water and 78.3g phenyl triethoxysilane are added under 50r/min stirring, is warming up to 60
DEG C, 18h is reacted, there is solid generation, suspension is formed, suspension is filtered, a large amount of ethanol washings, 190 DEG C of air blast drying, finally
The incomplete polycondensation cage type phenyl silsesquioxane of alkali metal containing sodium is obtained, yield is about 81.2%.
It is total that examination of infrared spectrum, nuclear-magnetism are carried out to the incomplete polycondensation cage type phenyl silsesquioxane of gained alkali metal containing sodium
Hydrogen spectrum of shaking test, MALDI-TOF-MS mass spectral analysis and thermogravimetric analysis, acquired results are similar to Example 1.
Embodiment 3
1000mL acetone is added to equipped with three mouthfuls of burnings with reflux condensing tube, temperature regulating device and magnetic stirring apparatus
In bottle, 28g sodium methoxide, 30mL distilled water and 313.2g phenyl triethoxysilane, heating are added under 80r/min stirring
To 65 DEG C, reaction for 24 hours, there is solid generation, forms suspension, suspension is filtered, a large amount of acetone washings, 180 DEG C of air blast drying,
The incomplete polycondensation cage type phenyl silsesquioxane of alkali metal containing sodium is finally obtained, yield is about 80.3%.
It is total that examination of infrared spectrum, nuclear-magnetism are carried out to the incomplete polycondensation cage type phenyl silsesquioxane of gained alkali metal containing sodium
Hydrogen spectrum of shaking test, MALDI-TOF-MS mass spectral analysis and thermogravimetric analysis, acquired results are similar to Example 1.
Embodiment 4
By 88mL acetone, 12mL methanol is added to equipped with reflux condensing tube, temperature regulating device and magnetic stirring apparatus
In three-necked flask, 1g NaOH, 1.8mL distilled water and 13.2g phenyltrimethoxysila,e are added under 30r/min stirring,
70 DEG C are warming up to, 12h is reacted, there is solid generation, suspension is formed, suspension is filtered, a large amount of acetone and methanol washing, 200
DEG C air blast drying, finally obtains the incomplete polycondensation cage type phenyl silsesquioxane of alkali metal containing sodium, yield is about 83.6%.
It is total that examination of infrared spectrum, nuclear-magnetism are carried out to the incomplete polycondensation cage type phenyl silsesquioxane of gained alkali metal containing sodium
Hydrogen spectrum of shaking test, MALDI-TOF-MS mass spectral analysis and thermogravimetric analysis, acquired results are similar to Example 1.
Embodiment 5
By 200mL acetone, 20mL isopropanol is added to equipped with reflux condensing tube, temperature regulating device and magnetic stirring apparatus
500mL three-necked flask in, 3g NaOH, 3.60mL distilled water and 26.5g phenyl front three are added under 40r/min stirring
Oxysilane, heating make to flow back in system, and the reaction was continued 20h has solid generation, form suspension, suspension is filtered,
A large amount of acetone and isopropanol washing, 180 DEG C of air blast drying, finally obtain the incomplete polycondensation cage type phenyl sesquialter of alkali metal containing sodium
Siloxanes, yield are about 76.6%.
It is total that examination of infrared spectrum, nuclear-magnetism are carried out to the incomplete polycondensation cage type phenyl silsesquioxane of gained alkali metal containing sodium
Hydrogen spectrum of shaking test, MALDI-TOF-MS mass spectral analysis and thermogravimetric analysis, acquired results are similar to Example 1.
As seen from the above embodiment, the incomplete polycondensation cage type phenyl silsesquioxane of alkali metal containing sodium provided by the invention
In contain Si-OH and Si-ONa active group, thermal stability is high, and preparation method is easy to operate, and synthesis cycle is short, and yield is high.
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 incomplete polycondensation cage type phenyl silsesquioxane of alkali metal containing sodium, which is characterized in that have and tied shown in Formulas I
Structure:
2. the preparation method of the incomplete polycondensation cage type phenyl silsesquioxane of alkali metal containing sodium described in claim 1, special
Sign is, comprising the following steps:
Phenyl trialkoxysilane, the alkaline matter containing metallic sodium, organic solvent and water are mixed, cyclic polycondensation reaction is carried out,
Obtain the incomplete polycondensation cage type phenyl silsesquioxane of alkali metal containing sodium.
3. preparation method according to claim 2, which is characterized in that the phenyl trialkoxysilane is phenyl trimethoxy
Base silane and/or phenyl triethoxysilane.
4. preparation method according to claim 2, which is characterized in that the alkaline matter containing metallic sodium is hydroxide
One or more of sodium, sodium ethoxide and sodium methoxide.
5. preparation method according to claim 2, which is characterized in that the organic solvent is tetrahydrofuran, methanol, second
One or more of alcohol, acetone, isopropanol, chloroform, methylene chloride, toluene and benzene.
6. preparation method according to claim 2, which is characterized in that the phenyl trialkoxysilane, containing metallic sodium
The molar ratio of alkaline matter and water is (0.5~1): (0.4~0.7): (0.8~1.8).
7. preparation method according to claim 2, which is characterized in that the phenyl trialkoxysilane and organic solvent
Amount ratio is (0.8~1) g:(1.5~7) mL.
8. preparation method according to claim 2, which is characterized in that the temperature of the cyclization polycondensation reaction is 55~70
DEG C, the time be 12~for 24 hours.
9. preparation method according to claim 2, which is characterized in that further include to described after the cyclization polycondensation reaction
Cyclic polycondensation reaction liquid is post-processed, it is described post-processing the following steps are included:
The cyclic polycondensation reaction liquid is successively filtered, washed and dried, the incomplete polycondensation cage of alkali metal containing sodium is obtained
Shape phenyl silsesquioxane solid.
10. preparation method according to claim 9, which is characterized in that the temperature of the drying is 180~200 DEG C.
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| CN115873382A (en) * | 2021-09-29 | 2023-03-31 | 广东中塑新材料有限公司 | Polybutylene terephthalate composition and preparation method thereof |
| CN116572603A (en) * | 2023-07-13 | 2023-08-11 | 浙江葆润应用材料有限公司 | Composite heat insulation material and application thereof |
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Application publication date: 20191115 |