CN110951262A - Preparation method of novel polysiloxane type hydrogen-absorbing polymer film material - Google Patents
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- C08J2483/00—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
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Abstract
The invention discloses a preparation method of a novel polysiloxane type hydrogen absorption polymer film material, which comprises the steps of crosslinking and curing polyvinyl siloxane resin containing a noble metal catalyst by a silanol condensation method at a certain temperature and for a certain time to obtain an elastic hydrogen absorption material; the invention uses the silanol condensation method to crosslink the vinyl resin to obtain the hydrogen-absorbing polymer, and because the silanol condensation reaction system is independent from the functional part (vinyl) and the catalytic part (Pd catalyst) of the hydrogen-absorbing polymer, the vinyl is not consumed in the curing reaction, and the saturated hydrogen absorption amount of the system is not reduced; in addition, because the Pd catalyst is not a silanol condensation reaction catalyst, the operation time of the system is only related to the time for adding the silanol condensation catalyst and the amount of the added catalyst, and the operation time of the system can be regulated and controlled according to the actual use condition, so that the practical use is facilitated.
Description
Technical Field
The invention relates to the chemical field of composite films, in particular to a preparation method of a novel polysiloxane type hydrogen absorption polymer film material.
Background
The room temperature irreversible hydrogen absorbent is a core functional component for controlling the atmosphere of a nuclear equipment closed system, and has important significance for the safety, reliability and service life of the nuclear equipment. The existing DEB-Pd/C composite hydrogen absorbent in the nuclear equipment in China can well and stably control the hydrogen concentration in a closed system to be lower than 100ppm, so that the storage environment of the equipment is improved to a great extent, and the storage reliability of the equipment is improved. However, the current method of placing the whole powder bag of the hydrogen absorbing agent in the application environment of narrow and complex space is greatly limited due to the difficulty of better adapting to the requirements of space position and shape. The hydrogen-absorbing polymer material which can be flexibly formed according to the use space position needs to be developed to meet the actual use requirement.
For the demand of polymer hydrogen absorption Materials, the currently reported method mainly adopts a method of compounding a polymer and a powder hydrogen absorption agent for preparation, and in the actual situation, due to the compatibility problem of the polymer and the hydrogen absorption agent and the influence of DEB on the mechanical property and curing molding of a polymer matrix, the method is difficult to obtain a hydrogen absorption polymer with excellent hydrogen absorption property and mechanical property (U.S. Pat. No. 5,5837158, Advanced Functional Materials 2018,28,7217085); we have previously reported a method (ZL201510673143.3) for preparing a polysiloxane-type hydrogen-absorbing polymer film material by hydrosilylation, but since the crosslinking reaction (hydrosilylation) in the curing reaction consumes more vinyl groups in the system and the vinyl groups are active groups for hydrogen reaction, it is difficult to obtain a material with high hydrogen absorption by this method, and in addition, because of the catalytic action of the noble metal Pd in the supported catalyst on the vinyl siloxane addition reaction, the mixed system often starts to cure before the Pt catalyst is added, so the operation time is short, which causes great difficulty for specific applications.
Disclosure of Invention
The present invention is directed to overcoming the deficiencies of the prior art and providing a method for preparing a novel siloxane hydrogen absorbing polymer composite based on a silanol condensation curing reaction, which solves at least one or more of the problems set forth above.
The purpose of the invention is realized by the following technical scheme:
a preparation method of a novel polysiloxane type hydrogen-absorbing polymer film material comprises the following steps:
a) preparation of a prepolymer: initiating polymerization by taking cyclosiloxane containing vinyl as a monomer under the action of a catalyst to obtain polyvinyl siloxane resin;
b) preparation of hydrogen-absorbing elastomer: fully mixing the obtained polyvinyl siloxane resin with noble metal-loaded powder and multifunctional silicate ester or silanol, heating at a certain temperature for a certain time for curing reaction, and finally obtaining the elastic hydrogen absorption material;
preferably, the vinyl-containing cyclosiloxane structure is as follows:
wherein R is1-R3Can be vinyl, methyl, hydrogen atom, alkoxy or any combination of the above groups.
Preferably, the catalyst in step a) is a basic catalyst or an acidic catalyst; the basic catalyst includes alkali metal hydroxide, quaternary ammonium (quaternary phosphine) hydroxide, etc., and the acidic catalyst includes sulfuric acid, trifluoromethanesulfonic acid, trifluoroacetic acid, acidic clay, sulfonic acid ion exchange resin, etc.
Preferably, the noble metal catalyst in step b) is Pt, Pd or Au; the load carrier is organic or inorganic porous substance, such as carbon black, SiO2，CaCO3，Al2O3Etc.; wherein the loading amount is 0-50%.
Preferably, the multifunctional silanol in step b) is a small molecule or a polymer molecule.
Preferably, the multifunctional group and silicate in step b) have the following structures:
wherein R is an alkyl group having 1 to 4 carbon atoms.
Preferably, the step b) increases the speed and degree of the curing reaction by adding a tin catalyst, wherein the tin catalyst is stannous octoate or dibutyltin dilaurate.
Preferably, the mixing in step b) is a manual stirring method or a mechanical stirring method.
Preferably, the reaction temperature in the step b) is 0-120 ℃, and the reaction time can be 0.5-120 h.
The invention has the beneficial effects that:
compared with the existing preparation method of the hydrogen-absorbing polymer, the invention uses the silanol condensation method to crosslink the vinyl siloxane resin to obtain the hydrogen-absorbing polymer, and because the silanol condensation reaction system is independent from the functional part (vinyl) and the catalytic part (Pd catalyst) of the hydrogen-absorbing polymer, the vinyl is not consumed in the curing reaction, and the saturated hydrogen-absorbing amount of the system is not reduced; in addition, because the Pd catalyst is not a silanol condensation reaction catalyst, the operation time of the system is only related to the time for adding the silanol condensation catalyst and the amount of the added catalyst, and the operation time of the system can be regulated and controlled according to the actual use condition, so that the practical use is facilitated.
Detailed Description
The technical solutions of the present invention are further described in detail below with reference to examples, but the scope of the present invention is not limited to the following.
Example 1
(1) Preparation of alkoxycyclotetrasiloxane
Wherein R is Si (OEt)3
20g of tetramethylcyclotetrasiloxane and 10ml of xylene were weighed into a 150ml round-bottom flask and bubbled with nitrogen for 15min to remove air from the system. Then, 10g of triethoxysilane and 0.1ml of the catalyst in the form of card were added and reacted at room temperature for 24 hours. After the reaction, adding activated carbon, stirring for 2h, filtering, and removing xylene under reduced pressure to obtain yellowish transparent liquid.
(2) Synthesis of alkoxy grafted polyvinyl methyl siloxane
100mL of tetramethyltetravinylcyclotetrasiloxane, 2mL of alkoxycyclotetrasiloxane and 0.2mL of hexamethyldisiloxane were weighed into a 250mL single-neck flask equipped with mechanical stirring, and then 0.1g of potassium hydroxide was added as a catalyst, and the reaction mixture was heated to 100 ℃ for reaction for 3 hours. And then adding 100mL of n-hexane to dissolve a reaction product, washing the obtained solution for three times by using deionized water, drying an organic phase by using magnesium sulfate after layering, and removing the solvent and low-molecular volatile matters in vacuum to obtain colorless transparent oily liquid.
(3) Preparation of composite hydrogen-absorbing polymer
2.0g of alkoxy-grafted polyvinyl methylsiloxane are weighed out, dissolved in 5ml of n-hexane and then 0.8g of Pd/C (5% by weight) and 0.05g of polysiloxane disiloxane (M)n24000, Sigma) was mechanically stirred well and then 15 μ was addedL dibutyltin dilaurate, stirring and mixing uniformly. The resulting black mixture was poured onto a glass plate, allowed to dissolve and then cured at room temperature for 2 days to obtain a black elastic composite film.
The obtained black elastic composite film (2.2g) was placed in a closed container (1L) filled with 146KPa pure hydrogen and tested at room temperature, and the pressure change conditions of the system at different times were as follows:
| time (hours) | 2 | 6 | 10 | 16 | 24 | 48 | 96 |
| Pressure (KPa) | 121 | 114 | 105 | 98 | 91 | 83 | 76 |
The hydrogen concentration of the resulting black film (0.2g) after exposure to a mixed gas (250mL of a 1% hydrogen-nitrogen mixture) over time was varied as follows:
| time per hour | 2 | 6 | 10 | 16 | 24 |
| Hydrogen gas concentration (%) | 0.7 | 0.3 | 0.1 | 0.05 | 0.02 |
Example 2
(1) Synthesis of silanol terminated polyvinyl methyl siloxane
100mL of tetramethyltetravinylcyclotetrasiloxane was measured and charged into a single-neck flask equipped with mechanical stirring, followed by 0.1g of potassium hydroxide. The reaction was heated to 100 ℃ for 3 h. And then adding 100mL of n-hexane to dissolve a reaction product, washing the obtained solution with dilute hydrochloric acid, then washing with deionized water for three times, drying an organic phase with magnesium sulfate after layering, and removing the solvent and low-molecular volatile matters in vacuum to obtain colorless transparent oily liquid.
(2) Preparation of composite hydrogen-absorbing polymer
2.0g of silanol terminated polyvinyl methyl siloxane was weighed, 5ml of n-hexane was added for dissolution, then 0.8g of Pd/C (5 wt%) and 0.03g of tetraethyl silicate were added, mechanically stirred well, 15. mu.L of dibutyltin dilaurate was added, stirred well and mixed well. The resulting black mixture was poured onto a glass plate, allowed to dissolve and then cured at room temperature for 2 days to obtain a black elastic composite film.
The resulting black film (2.2g) was placed in a closed container (1L) filled with 146KPa pure hydrogen and tested at room temperature, with the following pressure changes over the time frame:
| time (hours) | 2 | 6 | 10 | 16 | 24 | 48 | 96 |
| Pressure (KPa) | 102 | 90 | 86 | 75 | 72 | 68 | 65 |
The hydrogen concentration of the resulting black film (0.2g) after exposure to a mixed gas (250mL of a 1% hydrogen-nitrogen mixture) over time was varied as follows:
| time per hour | 2 | 6 | 10 | 16 | 24 |
| Hydrogen gas concentration (%) | 0.4 | 0.1 | 0.02 | 0.003 | 0.001 |
Example 3
Mixing the prepolymers 1:1 prepared in the embodiment 1 and the embodiment 2 to obtain a composite hydrogen absorbing material;
1.0g of alkoxy grafted polyvinyl methyl siloxane and 1.0g of silanol terminated polyvinyl methyl siloxane are weighed, 5ml of n-hexane is added for dissolution, 0.8g of Pd/C (5 wt%) is added, after mechanical stirring is carried out uniformly, 15 mu L of dibutyltin dilaurate is added, and stirring and mixing are carried out uniformly. The resulting black mixture was poured onto a glass plate, allowed to dissolve and then cured at room temperature for 2 days to obtain a black elastic composite film.
The resulting black film (2.2g) was placed in a closed container (1L) filled with 146KPa pure hydrogen and tested at room temperature, with the following pressure changes over the time frame:
| time (hours) | 2 | 6 | 10 | 16 | 24 | 48 | 96 |
| Pressure (KPa) | 105 | 93 | 88 | 76 | 71 | 67 | 63 |
The hydrogen concentration of the resulting black film (0.2g) after exposure to a mixed gas (250mL of a 1% hydrogen-nitrogen mixture) over time was varied as follows:
| time per hour | 2 | 6 | 10 | 16 | 24 |
| Hydrogen gas concentration (%) | 0.5 | 0.09 | 0.02 | 0.002 | 0.001 |
The foregoing is illustrative of the preferred embodiments of this invention, and it is to be understood that the invention is not limited to the precise form disclosed herein and that various other combinations, modifications, and environments may be resorted to, falling within the scope of the concept as disclosed herein, either as described above or as apparent to those skilled in the relevant art. And that modifications and variations may be effected by those skilled in the art without departing from the spirit and scope of the invention as defined by the appended claims.
Claims (9)
1. A preparation method of a novel polysiloxane type hydrogen-absorbing polymer film material is characterized by comprising the following steps: the method comprises the following steps:
a) preparation of a prepolymer: taking cyclosiloxane containing vinyl as a monomer, adding a catalyst to initiate polymerization to obtain polyvinyl siloxane resin;
b) preparation of hydrogen-absorbing elastomer: and fully mixing the obtained polyvinyl siloxane resin with noble metal-loaded powder and multifunctional silicate ester or silanol, heating and curing to obtain the elastic hydrogen absorbing material.
2. The method for producing a novel polysiloxane-based hydrogen absorbing polymer film material according to claim 1, wherein: the vinyl-containing cyclosiloxane structure is as follows:
wherein R is1-R3Is vinyl, methyl, hydrogen atom, alkoxy or any combination of the above groups.
3. The method for producing a novel polysiloxane-based hydrogen absorbing polymer film material according to claim 1, wherein: the catalyst in the step a) is a basic catalyst or an acidic catalyst.
4. The method for producing a novel polysiloxane-based hydrogen absorbing polymer film material according to claim 1, wherein: the noble metal catalyst in the step b) is Pt, Pd or Au; the load carrier is an organic or inorganic porous substance.
5. The method for producing a novel polysiloxane-based hydrogen absorbing polymer film material according to claim 1, wherein: the multifunctional silanol in the step b) is a small molecule or a polymer molecule.
6. The method for producing a novel polysiloxane-based hydrogen absorbing polymer film material according to claim 1, wherein: the multifunctional silicate in the step b) has the following structure:
wherein R is an alkyl group of 1 to 4 carbon atoms.
7. The method for producing a novel polysiloxane-based hydrogen absorbing polymer film material according to claim 1, wherein: the step b) is to increase the speed and the degree of the curing reaction by adding tin catalyst.
8. The method for producing a novel polysiloxane-based hydrogen absorbing polymer film material according to claim 1, wherein: the mixing in the step b) is a manual stirring method or a mechanical stirring method.
9. The method for preparing a novel polysiloxane type hydrogen absorbing polymer film material according to claim 1, wherein the reaction temperature in step b) is 0 ℃ to 120 ℃ and the reaction time is 0.5 to 120 h.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112321830A (en) * | 2020-11-09 | 2021-02-05 | 中国工程物理研究院总体工程研究所 | Organic silicon resin with hydrogen absorption function and preparation method thereof |
| CN112341822A (en) * | 2020-11-09 | 2021-02-09 | 中国工程物理研究院总体工程研究所 | Polymer film material with hydrogen absorption function and preparation method thereof |
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| CN1336856A (en) * | 1999-11-10 | 2002-02-20 | 信越化学工业株式会社 | Hydrogen storage composite formed article and method for preparing the same |
| CN105153449A (en) * | 2015-10-13 | 2015-12-16 | 中国工程物理研究院总体工程研究所 | High-molecular composite thin film capable of absorbing hydrogen and preparation method of high-molecular composite thin film |
| CN109384976A (en) * | 2018-11-23 | 2019-02-26 | 西南科技大学 | A kind of flexibility disappears the preparation method of hydrogen thin-film material |
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Patent Citations (4)
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| US5258435A (en) * | 1991-03-13 | 1993-11-02 | Bayer Aktiengesellschaft | Palladium-containing polymer composition and a process for its preparation |
| CN1336856A (en) * | 1999-11-10 | 2002-02-20 | 信越化学工业株式会社 | Hydrogen storage composite formed article and method for preparing the same |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112321830A (en) * | 2020-11-09 | 2021-02-05 | 中国工程物理研究院总体工程研究所 | Organic silicon resin with hydrogen absorption function and preparation method thereof |
| CN112341822A (en) * | 2020-11-09 | 2021-02-09 | 中国工程物理研究院总体工程研究所 | Polymer film material with hydrogen absorption function and preparation method thereof |
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