CN115477926B - Phase change material and preparation method thereof - Google Patents
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- 239000012782 phase change material Substances 0.000 title claims abstract description 40
- 238000002360 preparation method Methods 0.000 title abstract description 17
- 239000013078 crystal Substances 0.000 claims abstract description 25
- 239000002253 acid Substances 0.000 claims abstract description 13
- 238000003756 stirring Methods 0.000 claims description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- UUZYBYIOAZTMGC-UHFFFAOYSA-M benzyl(trimethyl)azanium;bromide Chemical class [Br-].C[N+](C)(C)CC1=CC=CC=C1 UUZYBYIOAZTMGC-UHFFFAOYSA-M 0.000 claims description 7
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 6
- NVNPLEPBDPJYRZ-UHFFFAOYSA-N 1-(bromomethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CBr)C=C1 NVNPLEPBDPJYRZ-UHFFFAOYSA-N 0.000 claims description 2
- OINMNSFDYTYXEQ-UHFFFAOYSA-M 2-bromoethyl(trimethyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCBr OINMNSFDYTYXEQ-UHFFFAOYSA-M 0.000 abstract description 19
- 229910052799 carbon Inorganic materials 0.000 abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 6
- 239000002245 particle Substances 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 238000005979 thermal decomposition reaction Methods 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 23
- 239000012071 phase Substances 0.000 description 22
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 16
- 230000008859 change Effects 0.000 description 13
- 239000000463 material Substances 0.000 description 9
- 238000010586 diagram Methods 0.000 description 5
- 238000013461 design Methods 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- 150000001449 anionic compounds Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000005669 field effect Effects 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 229910001412 inorganic anion Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000000634 powder X-ray diffraction Methods 0.000 description 2
- 238000001338 self-assembly Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 230000000666 effect on cation Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004146 energy storage Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005381 potential energy Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000011232 storage material Substances 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/06—Materials undergoing a change of physical state when used the change of state being from liquid to solid or vice versa
- C09K5/063—Materials absorbing or liberating heat during crystallisation; Heat storage materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/62—Quaternary ammonium compounds
- C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/14—Thermal energy storage
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Combustion & Propulsion (AREA)
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Abstract
The invention discloses a phase change material and a preparation method thereof, wherein R=H or F in the structural general formula of the phase change material, namely the molecular formula of the phase change material is C 10H16BF4 N or C 10H15BF5 N, and the phase change material is in a crystal structure; the phase change material is prepared by mixing tetrafluoroboric acid solution and BTAB or BTAB derivatives, and self-assembling by naturally volatilizing solvent. The phase change material disclosed by the invention has relatively high thermal decomposition temperature point and uniform crystal particles; meanwhile, the preparation process is simple, easy to operate, sufficient in raw material source, low in production cost, high in yield and good in repeatability.
Description
Technical Field
The invention relates to a material and a preparation method thereof, in particular to a phase change material and a preparation method thereof.
Background
Phase change materials (PCM-PHASE CHANGE MATERIAL) are materials that change their morphology by changing temperature and can also provide latent heat. When the crystal is subjected to external temperature, pressure and the like, the symmetry of the crystal point group in the same solid phase changes, namely the phase change of the crystal structure occurs. For temperature induced phase changes in the crystal structure, the symmetry of the crystal generally follows the higher symmetry at the high temperature phase and the lower symmetry at the low temperature phase. In general, from the high temperature phase to the low temperature phase, the symmetry of the crystal structure becomes low, and the loss of the symmetry manipulating element is called symmetry breaking. When the phase change occurs, the dielectric property, the thermal entropy change and the phase change of the crystal structure are all obviously abnormal.
Since the beginning of the new century, excessive use of petroleum and coal has resulted in serious pollution to the ecological environment and impairment of human health. The development of industrial new energy is urgently needed in China, and sustainable development is realized. The phase change material is used as an excellent energy storage material and is widely applied in the fields of aerospace, construction, military and the like. Phase change materials are classified according to material composition, and mainly include three types of inorganic, organic, and organic-inorganic. Among them, organic-inorganic hybrid phase change materials have attracted attention from many scholars in the field due to their advantages of simple synthesis, flexible and diverse structures, environmental friendliness, and the like.
With the progress of science and technology and the continuous improvement of theory, accurate molecular design can synthesize the phase change material with excellent performance. However, only by considering the efficient selection of molecular units and the efficient selection of intermolecular interactions, the intentional design of phase changes can be fully achieved. In the research of literature Tang,Y.Y.;Xie,Y.;Zeng,Y.L.;Liu,J.C.;He,W.H.;Huang,X.Q.;Xiong,R.G.Record enhancement of phase transition temperature realized by H/F substitution.Adv.Mater.2020,32,e2003530.Xu,Q.;Ye,L.;Liao,R.M.;An,Z.;Wang,C.F.;Miao,L.P.;Shi,C.;Ye,H.Y.;Zhang,Y.H/F substitution induced large increase of Tc in a 3D hybrid rare-earth double perovskite multifunctional compound.Chem.2022,28,e202103913. and the like, an organic-inorganic hybrid material is obtained through H/F substitution, and F atoms are introduced to increase the rotation potential energy of cations so as to improve the phase transition temperature. However, the phase transition temperature of the fluoride of the target product is still low, the performance is single, and the application range of the fluoride is severely limited.
Disclosure of Invention
The invention aims to: the invention aims to provide a high-temperature phase change material with uniform crystal particles formed by self-assembly; another object of the present invention is to provide a method for preparing a phase change material with simple operation, good reproducibility and high yield.
The technical scheme is as follows: the structural general formula of the phase change material is shown as formula (1), wherein R=H or F, and the phase change material has a crystal structure.
Preferably, at 296K, the crystal structure belongs to the monoclinic system.
Preferably, at 296K, the crystal structure belongs to the P2 1/n space group.
The preparation method of the phase change material comprises the following steps: slowly adding BTAB or BTAB derivatives into an organic solvent, stirring and dissolving, then adding tetrafluoroboric acid solution, fusing the two solutions, stirring uniformly, and standing to obtain the phase change material.
Preferably, the molar ratio of tetrafluoroboric acid to BTAB or BTAB derivatives is 1:1-1:2. the derivative of BTAB is prepared by reacting p-fluorobenzyl bromide and trimethylamine.
Preferably, the stirring time is 30-60min, the stirring temperature is 30-40 ℃, and the standing time is 2-3 weeks.
Preferably, the organic solvent is ethanol or acetonitrile.
The invention obtains two organic-inorganic hybrid phase change materials by adjusting organic cations, has no toxicity and low cost, and meets the requirements of green chemistry. Meanwhile, the high phase-change temperature material is successfully obtained through the finite field effect induced by the introduction of F atoms, and the application market of the material is widened. The discovery of the invention not only enriches the application content of the mixed material in the green energy field, but also provides a feasible way for exploring the multifunctional high-phase-change-temperature material.
The beneficial effects are that: compared with the prior art, the invention has the following remarkable advantages: (1) The phase change material has uniform crystal particles and good stability, belongs to the field of molecular ionic groups, has relatively high thermal decomposition temperature points, has uniform crystal particles, and can be used for synthesizing aerospace, building materials, clothing, military and other aspects to construct energy-saving equipment; (2) The preparation method is simple and easy to operate, the preparation method provided by the invention is synthesized by self-assembly through a solvent volatilization method at room temperature, the structural stability of the material is higher, the structural flexibility of the compound is good, the regulation and control are easy, the yield is high, the repeatability is good, the source of the adopted raw materials is sufficient, and the production cost is low.
Drawings
FIG. 1 is a design roadmap of the present invention;
FIG. 2 is a synthetic route diagram of a phase change compound of the present invention;
FIG. 3 is a unit cell diagram of the phase change compound of example 1 at 296K;
FIG. 4 is a graph showing the bottom-limit-area effect analysis of the phase change compound of example 1 at 296K;
FIG. 5 is an infrared spectrum of the phase change compound of example 1;
FIG. 6 is a powder PXRD diffraction pattern of the phase change compound of example 1;
FIG. 7 is a thermogravimetric TGA analysis of the phase change compound of example 1;
FIG. 8 is a differential scanning calorimetric diagram of the phase change compound of example 1.
Detailed Description
The technical scheme of the invention is further described below with reference to the accompanying drawings.
Example 1
The general structural formula of the phase change material is shown as formula (1), wherein R=H or F, and the phase change material has a crystal structure. I.e. its molecular formula is C 10H16BF4 N or C 10H15BF5 N.
The preparation of compound C 10H16BF4 N is as follows: at normal temperature, 1mol BTAB (BTAB =benzyltrimethylammonium bromide) is placed into a beaker, a proper amount of absolute ethyl alcohol is slowly added for stirring and dissolving, then 1mol of high-symmetry tetrafluoroboric acid solution is added for mutually fusing the two solutions, after stirring is carried out for 30 minutes at the temperature of 30 ℃, the solution is kept stand for 2 weeks at the room temperature, and the phase-change compound C 10H16BF4 N is obtained.
The preparation of compound C 10H15BF5 N is as follows: 20mmol of p-fluorobenzyl and 20mmol of trimethylamine were weighed into a flask and 40ml of acetonitrile solvent was added. The three are mixed uniformly and then reacted in an oil bath at 45 ℃ for 24 hours. Then spin-steaming at 50deg.C for 3h to obtain BTAB derivatives. And (3) at normal temperature, placing the derivative of 1mol BTAB into a beaker, slowly adding a proper amount of absolute ethyl alcohol, stirring and dissolving, then adding 1mol of highly symmetrical tetrafluoroboric acid solution to fuse the two solutions, stirring for 30 minutes at the temperature of 30 ℃, and standing for 2 weeks at the room temperature to obtain the phase-change compound C 10H15BF5 N.
Example 2
The general structural formula of the phase change material is shown as formula (1), wherein R=H or F, and the phase change material has a crystal structure. I.e. its molecular formula is C 10H16BF4 N or C 10H15BF5 N.
The preparation of compound C 10H16BF4 N is as follows: at normal temperature, 1.5mol BTAB (BTAB =benzyltrimethylammonium bromide) is placed into a beaker, a proper amount of absolute ethyl alcohol is slowly added for stirring and dissolving, then 1mol of high symmetry tetrafluoroboric acid solution is added for mutually fusing the two solutions, after stirring for 40 minutes at the temperature of 35 ℃, the solution is kept stand for 3 weeks at the room temperature, and the phase-change compound C 10H16BF4 N is obtained.
The preparation of compound C 10H15BF5 N is as follows: at normal temperature, 1.5mol of BTAB-derivative prepared in example 1 is placed into a beaker, a proper amount of absolute ethyl alcohol is slowly added for stirring and dissolving, then 1mol of highly symmetrical tetrafluoroboric acid solution is added for mutually fusing the two solutions, after stirring for 40 minutes at 35 ℃, the solution is left to stand for 3 weeks at room temperature, and the phase-change compound C 10H15BF5 N is obtained.
Example 3
The general structural formula of the phase change material is shown as formula (1), wherein R=H or F, and the phase change material has a crystal structure. I.e. its molecular formula is C 10H16BF4 N or C 10H15BF5 N.
The preparation of compound C 10H16BF4 N is as follows: at normal temperature, 2mol BTAB (BTAB =benzyltrimethylammonium bromide) is placed into a beaker, a proper amount of absolute ethyl alcohol is slowly added for stirring and dissolving, then 1mol of high-symmetry tetrafluoroboric acid solution is added for mutually fusing the two solutions, after stirring for 50 minutes at the temperature of 40 ℃, the solution is kept stand for 3 weeks at the room temperature, and the phase-change compound C 10H16BF4 N is obtained.
The preparation of compound C 10H15BF5 N is as follows: at normal temperature, 2mol of BTAB derivative prepared in example 1 is placed into a beaker, a proper amount of absolute ethyl alcohol is slowly added for stirring and dissolving, then 1mol of highly symmetrical tetrafluoroboric acid solution is added for mutually fusing the two solutions, after stirring for 50 minutes at 40 ℃, the solution is kept stand for 3 weeks at room temperature, and the phase-change compound C 10H15BF5 N is obtained.
Example 4
The general structural formula of the phase change material is shown as formula (1), wherein R=H or F, and the phase change material has a crystal structure. I.e. its molecular formula is C 10H16BF4 N or C 10H15BF5 N.
The preparation of compound C 10H16BF4 N is as follows: at normal temperature, 1.8mol BTAB (BTAB =benzyltrimethylammonium bromide) is placed into a beaker, a proper amount of absolute ethyl alcohol is slowly added for stirring and dissolving, then 1mol of high symmetry tetrafluoroboric acid solution is added for mutually fusing the two solutions, after stirring for 60 minutes at the temperature of 40 ℃, the solution is kept stand for 2 weeks at the room temperature, and the phase-change compound C 10H16BF4 N is obtained.
The preparation of compound C 10H15BF5 N is as follows: at normal temperature, 1.8mol of the derivative BTAB prepared in the embodiment 1 is placed into a beaker, a proper amount of absolute ethyl alcohol is slowly added for stirring and dissolving, then 1mol of high-symmetry tetrafluoroboric acid solution is added for mutually fusing the two solutions, the mixture is stirred for 60 minutes at the temperature of 40 ℃, and then the mixture is kept stand for 2 weeks at the room temperature, so that the phase-change compound C 10H15BF5 N is obtained.
FIG. 1 is a schematic diagram of the design of the present invention, and FIG. 2 is a schematic diagram of the synthesis of the phase change compound of the present invention.
The phase-change compound crystals prepared in example 1 were analyzed, and single crystals of a suitable size were selected under a microscope, and at room temperature, mo K. Alpha. Rays were monochromised with graphiteThe crystallographic parameters of the single crystal were determined on a Bruker Apex II CCD diffractometer and the results are shown in table 1. Semi-empirical absorption correction was performed using the SADABS method, unit cell parameters were determined using the least squares method, data reduction and structural analysis were accomplished using the SAINT and SHELXL packages, respectively, all non-hydrogen atoms were anisotropically refined using the full matrix least squares method, and the unit cell changes of the compounds are shown in FIG. 3. As can be seen from the figure, at 296K, the asymmetric unit of the compound consists of one cation and one anion. The B atom in the inorganic anion coordinates to 4F atoms, forming a slightly distorted tetrahedral BF 4 -. At 296K, both C 10H16BF4 N and C 10H15BF5 N belong to the monoclinic system, P2 1/N space group.
Crystallographic data for the compounds of table 1
FIG. 4 is a graph showing the analysis of the lower limit field effect of the compound of example 1 at 296K, wherein the closed plane composed of 4 inorganic anions has obvious space shrinkage after F substitution, which means that the constraint effect on cations is increased and the rotation space of cations is reduced, as shown in FIG. 4.
FIG. 5 is an infrared spectrum of the compound of example 1, which shows that there is a strong absorption peak at 2947cm -1, which is the absorption peak of-CH 3, as shown in FIG. 5.
Fig. 6 is a PXRD analysis characterization of the compound of example 1, from which it can be seen that the simulated diffraction peaks and the actual experimental diffraction peaks match, verifying the phase purity.
FIG. 7 is a thermogravimetric TGA analysis of the compound of example 1, as shown in FIG. 7, showing a very high stability of the compound. About 600K, the skeleton price in the compound starts to decompose; at 800 ℃, the compound completely collapsed.
FIG. 8 is a differential scanning calorimetry plot of the compounds of example 1, as shown in FIG. 8, with phase transition temperatures of 410.4K and 488.4K for the two compounds, respectively.
Claims (7)
1. A phase change material is characterized in that the general structural formula is shown as formula (1), wherein R=F, and the phase change material has a crystal structure
2. The phase change material of claim 1, wherein the crystal structure belongs to a monoclinic system at a temperature of 296K.
3. The phase change material of claim 1, wherein the crystal structure belongs to the P2 1/n space group at 296K.
4. A method of preparing a phase change material according to claim 1, comprising the steps of: slowly adding the benzyl trimethyl ammonium bromide derivative into ethanol or acetonitrile, stirring and dissolving, then adding tetrafluoroboric acid solution, fusing the two solutions, uniformly stirring, and standing to obtain the phase change material; the benzyl trimethyl ammonium bromide derivative is prepared by reacting p-fluorobenzyl bromide and trimethylamine.
5. The method for preparing a phase change material according to claim 4, wherein the molar ratio of tetrafluoroboric acid to the derivative of benzyltrimethylammonium bromide is 1:1-1:2.
6. The method of preparing a phase change material according to claim 4, wherein the stirring time is 30-60min and the stirring temperature is 30-40 ℃.
7. The method of preparing a phase change material according to claim 4, wherein the standing time is 2 to 3 weeks.
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| JP2005272366A (en) * | 2004-03-25 | 2005-10-06 | Koei Chem Co Ltd | Method for producing quaternary ammonium compound |
| CN103635582A (en) * | 2011-06-10 | 2014-03-12 | 先正达参股股份有限公司 | Methods for treating lignocellulosic material |
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| DE10305391A1 (en) * | 2003-02-11 | 2004-08-19 | Aventis Pharma Deutschland Gmbh | Preparation of 1-(pyridinyl)-1,1-dialkoxy-1-aminoethane derivatives involves reacting acetylpyridine tosyl oxime with mixture of alkali metal alkoxide or hydroxide or alkaline earth metal alkoxide or hydroxide with alcohol |
| JP2005145924A (en) * | 2003-11-19 | 2005-06-09 | Koei Chem Co Ltd | Quaternary ammonium salt |
| US7601871B2 (en) * | 2005-03-04 | 2009-10-13 | Honeywell International Inc. | Method for purifying quaternary onium salts |
| JP2011168576A (en) * | 2010-02-05 | 2011-09-01 | Rohm & Haas Co | Method of preparing organometallic compound |
| CN101845215B (en) * | 2010-04-02 | 2011-12-14 | 中国科学技术大学 | Preparation method based on brominated polyphenylether blending of hybrid anion exchange membrane |
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| JP2005272366A (en) * | 2004-03-25 | 2005-10-06 | Koei Chem Co Ltd | Method for producing quaternary ammonium compound |
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