CN108467469A - A kind of photothermal conversion polyurethane energy storage thin-film material and preparation method thereof and film - Google Patents
A kind of photothermal conversion polyurethane energy storage thin-film material and preparation method thereof and film Download PDFInfo
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- CN108467469A CN108467469A CN201810067001.6A CN201810067001A CN108467469A CN 108467469 A CN108467469 A CN 108467469A CN 201810067001 A CN201810067001 A CN 201810067001A CN 108467469 A CN108467469 A CN 108467469A
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- 238000006243 chemical reaction Methods 0.000 title claims abstract description 64
- 238000004146 energy storage Methods 0.000 title claims abstract description 62
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 46
- 239000004814 polyurethane Substances 0.000 title claims abstract description 46
- 239000000463 material Substances 0.000 title claims abstract description 45
- 239000010408 film Substances 0.000 title claims abstract description 35
- 239000010409 thin film Substances 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 239000000975 dye Substances 0.000 claims abstract description 86
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 36
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 36
- 150000002009 diols Chemical class 0.000 claims abstract description 34
- 229920000728 polyester Polymers 0.000 claims abstract description 24
- 229920000570 polyether Polymers 0.000 claims abstract description 24
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 29
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 22
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 20
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 14
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 10
- -1 small molecule diol Chemical class 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 4
- 239000001000 anthraquinone dye Substances 0.000 claims description 4
- 239000000987 azo dye Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 4
- 229920000909 polytetrahydrofuran Polymers 0.000 claims description 4
- 238000001291 vacuum drying Methods 0.000 claims description 4
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 3
- 239000004970 Chain extender Substances 0.000 claims description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 2
- 229920000921 polyethylene adipate Polymers 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 229920001451 polypropylene glycol Polymers 0.000 claims description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 230000008859 change Effects 0.000 abstract description 23
- 239000012071 phase Substances 0.000 abstract description 19
- 239000011232 storage material Substances 0.000 abstract description 12
- 239000012782 phase change material Substances 0.000 abstract description 11
- 239000002994 raw material Substances 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 229920006264 polyurethane film Polymers 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 239000012074 organic phase Substances 0.000 abstract description 2
- 238000009825 accumulation Methods 0.000 abstract 1
- 238000005516 engineering process Methods 0.000 abstract 1
- 238000004513 sizing Methods 0.000 abstract 1
- 150000003384 small molecules Chemical class 0.000 abstract 1
- 230000009466 transformation Effects 0.000 abstract 1
- 238000010521 absorption reaction Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 239000007790 solid phase Substances 0.000 description 4
- 239000002131 composite material Substances 0.000 description 3
- 238000005338 heat storage Methods 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- 229920001030 Polyethylene Glycol 4000 Polymers 0.000 description 1
- 239000004353 Polyethylene glycol 8000 Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229940093429 polyethylene glycol 6000 Drugs 0.000 description 1
- 229940085678 polyethylene glycol 8000 Drugs 0.000 description 1
- 235000019446 polyethylene glycol 8000 Nutrition 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6603—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6607—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
- C08G18/3874—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing heterocyclic rings having at least one sulfur atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
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- 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
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- 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
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- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
- C08J2375/06—Polyurethanes from polyesters
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
- C08J2375/08—Polyurethanes from polyethers
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Abstract
The present invention relates to a kind of photothermal conversion polyurethane energy storage thin-film material in phase-changing energy storage material field and preparation method thereof and films.The photothermal conversion polyurethane energy storage thin-film material, by being prepared comprising following components：Polyethylene glycol, oligomer polyethers or polyester diol, diisocyanate, small molecule dihydric alcohol, double hydroxy dyes；The molecular weight of the polyethylene glycol is 2000~20000；The oligomer polyethers or the molecular weight of polyester diol are 500~3000；Double hydroxy dyes contain there are two free active hydroxyl groups, can absorb the visible light of 380~780nm；The polyurethane film of the present invention makes film have both photothermal conversion and thermal energy storage function, can effectively solve deformation, the leakage problem of organic phase change material by the heat accumulation characteristic of dyestuff and sizing phase-change material that covalent bond is keyed in；Polyurethane film phase transformation enthalpy provided by the invention is high, and performance is stablized, and synthesis technology is relatively easy, and raw material is easy to get, and has very wide application prospect.
Description
Technical Field
The invention relates to the field of phase change energy storage materials, in particular to a photothermal conversion polyurethane energy storage thin film material, a preparation method thereof and a thin film.
Background
At present, the problem of energy shortage is the biggest problem facing the current society, the development and utilization of new energy is an important way to solve the energy problem, clean and renewable energy sources such as solar energy, hydroenergy, tidal energy and the like are widely concerned, but the energy sources have the defects of intermittency, discontinuity, mismatching and the like, and can not provide energy continuously and stably, so that a phase change energy storage material is needed to realize the continuous supply of energy.
The use of heat energy is the most extensive in all forms of energy utilization, and most of the energy utilization processes meet the production and life of human beings through a way of heat energy conversion. However, there is a large amount of energy loss and serious waste of resources in the process of utilizing heat energy. In addition, the temporal and spatial mismatch of energy utilization also results in a waste of resources. Therefore, how to efficiently utilize heat energy is an effective way to solve the problems of large heat energy loss and low utilization rate. Solar energy utilization is one of the simplest, most direct and most effective ways, and has become a research hotspot for high-efficiency utilization of solar energy, but the direct utilization of solar energy is greatly limited due to the fact that the energy density of solar radiation reaching the earth surface is low and is influenced by natural factors such as seasons, climates, time and the like, and in order to solve the problems, an effective energy storage device is needed to store solar energy and release the solar energy when needed, so that the demand of people is met.
The solar energy utilization equipment comprises a solar radiation energy collection and conversion device and a thermal energy storage device. Materials that absorb solar radiation energy and convert it to thermal energy include inorganic materials, semiconductors, and organic dyes. The organic dye has double characteristics of light absorption and photothermal conversion, wherein the organic dye contains reactive groups, and can be easily combined with the phase-change material in a chemical bond mode, so that the problem of phase separation after photothermal conversion phase change is solved, and the material integrating light capture, photothermal conversion and energy storage can be prepared.
The phase change energy storage material is divided into an inorganic phase change material, an organic phase change material and a composite phase change material. The organic shape-stabilized phase change energy storage material has the advantages of stable shape, small volume change, no leakage, no corrosion and the like, and becomes one of the research hotspots of the phase change energy storage material. The polyethylene glycol is used as a raw material to synthesize the most representative polyurethane phase change energy storage material, for example, Mu Siyang and the like graft polystyrene acrylonitrile on the polyethylene glycol to prepare a novel solid-solid phase change material, the phase change enthalpy value is 68.3kJ/kg, and the novel solid-solid phase change material still maintains higher heat storage capacity and has better thermal stability after 1000 cycles. The Liu Zhineng and the like take PEG4000 as a phase change material, castor oil as a framework and MDI and HDI as connecting groups to synthesize the novel polyurethane solid-solid phase change material, wherein the phase change enthalpy value is 117.7J/g, and the novel polyurethane solid-solid phase change material has excellent thermal stability and reliability and has a great application prospect in the aspect of solar heat storage.
The characteristics of the dye on light absorption and light-heat conversion enable the research of the dye introduced into the phase-change material to be more and more extensive, and the Chinese patent with the publication number of CN 102532945A introduces a multi-block type high molecular organic shape-stabilized phase-change dye with polyethylene glycol as a soft segment and a hard segment, and the dye can be used for the light-heat conversion and storage of solar energy and can also be used for dyeing and printing. Chinese patent publication No. CN106047305A discloses a method for preparing a photothermal conversion type organic/inorganic composite energy storage material, in which polyethylene glycol is used as a phase change component, a dye is bonded to a silica support material in the form of a chemical bond, and the composite phase change material integrating photothermal conversion and energy storage is prepared, and has high energy storage density and high coating rate. However, the prepared energy storage material is powder, and the phase change material exists in the energy storage material in a coated form, so that the risk of leakage exists.
Disclosure of Invention
In order to solve the problems in the prior art, the invention provides a photothermal conversion polyurethane energy storage film material. In particular to a photothermal conversion polyurethane energy storage film material, a preparation method thereof and a film. The photothermal conversion polyurethane energy storage film is a polyurethane energy storage film integrating light capture, photothermal conversion and heat energy storage, the film takes polyethylene glycol, low-polymer polyester or polyether diol as a soft segment, and takes dihydroxyl dye, diisocyanate and micromolecule diol as a hard segment, wherein the dye can absorb visible light and carry out photothermal conversion, and the polyethylene glycol is a phase change energy storage component; the polyurethane film has the advantages that the polyurethane film has the photo-thermal conversion and the heat energy storage functions, the dye is input through the covalent bond, and the heat storage characteristic of the shaped phase-change material is realized, so that the film has the photo-thermal conversion and the heat energy storage functions, the problems of deformation and leakage of the organic phase-change material can be effectively solved, the synthesis process is relatively simple, and the application is convenient.
One of the purposes of the invention is to provide a photothermal conversion polyurethane energy storage film material, which is prepared from components including polyethylene glycol, oligomer polyether or polyester diol, diisocyanate, dihydroxyl dye and micromolecule diol, wherein the structural formula of the photothermal conversion polyurethane energy storage film material can be as follows:
wherein: r is a diisocyanate component, R2The oligomer diol component, Dye, n, is determined by the molecular weight of polyethylene glycol, and may be 2000-20000.
The invention also aims to provide a preparation method of the photothermal conversion polyurethane energy storage thin film material, which comprises the following steps:
(1) vacuum drying the polyethylene glycol and the oligomer polyether or polyester diol to remove water; specifically, the raw materials can be treated for 2 to 3 hours in a vacuum drying oven at the temperature of between 60 and 80 ℃ to remove the moisture contained in the raw materials;
(2) dissolving the treated polyethylene glycol and oligomer polyether or polyester diol and the diisocyanate in N, N-dimethylformamide according to the amount, wherein the components are fully dissolved by the amount of the N, N-dimethylformamide, and reacting at the temperature of 30-40 ℃ for 2-3 h in the nitrogen atmosphere to obtain a polyurethane prepolymer;
(3) dissolving the dihydroxy dye into a solvent according to the amount, adding the solvent in an amount that the dye is fully dissolved, adding the solvent into the polyurethane prepolymer, raising the temperature to 60-70 ℃ for reaction, wherein the reaction time can be 1-2 h; the solvent is selected from at least one of N, N-Dimethylformamide (DMF), acetone or dichloromethane;
(4) and finally, adding a micromolecular diol chain extender, raising the temperature to 80-90 ℃ for reaction, wherein the reaction time can be 2-3 h, and obtaining a polyurethane solution, namely the photothermal conversion polyurethane energy storage film material.
Further, the photothermal conversion polyurethane energy storage film material (polyurethane solution) can be poured into a polytetrafluoroethylene mold, the mold is dried, and specifically, the mold can be placed in a drying oven at 60-80 ℃ for drying for 8-10 hours, so that the photothermal conversion polyurethane energy storage film is obtained.
Wherein,
the molar ratio of the oligomer polyether or polyester diol to the polyethylene glycol is (0-15): 1, preferably (0 to 8): 1;
the molar ratio of the sum of the mole numbers of the polyethylene glycol, the oligomer polyether or the polyester diol to the mole number of the micromolecular diol is 1: (0.5 to 10), preferably 1: (0.7-5);
the molar ratio of the sum of hydroxyl groups in the polyethylene glycol, the oligomer polyether or the polyester diol to isocyanate groups in the diisocyanate is 1: (1 to 7), preferably 1: (2-5);
the molar ratio of the sum of hydroxyl groups in the polyethylene glycol, the oligomer polyether or polyester diol and the micromolecule diol to the isocyanate group in the diisocyanate is (1-2): 1, preferably (1 to 1.5): 1.
the molecular weight of the polyethylene glycol is 2000-20000, and is preferably 4000-10000;
the molecular weight of the oligomer polyether or polyester diol is 500-3000, preferably 1000-2500;
the diisocyanate is selected from at least one of 4, 4' -diphenylmethane diisocyanate (MDI), isophorone diisocyanate and toluene diisocyanate.
The oligomer polyether or polyester diol can be selected from at least one of polypropylene glycol, polytetrahydrofuran ether glycol, polybutylene adipate glycol and polyethylene adipate glycol;
the micromolecular dihydric alcohol is at least one selected from ethylene glycol, 1, 4-butanediol and 1, 6-hexanediol.
The amount of the dihydroxy dye accounts for 0.1-3%, preferably 0.2-1% of the total mass of the polyethylene glycol, the oligomer polyether or polyester diol, the diisocyanate and the micromolecule diol.
The dihydroxy dye is azo dye or anthraquinone dye containing two active hydroxy groups.
The azo dye can be selected from at least one of dye A, dye B, dye C and dye D;
wherein the structure of the dye A is structural formula (1):
in the formula (1), R is H, Cl, CN, NO2CONHR 'or COOR'; wherein R' is H,CnH2n+1N is not less than 1 and not more than 18, and n is an integer;
wherein the structure of the dye B is structural formula (2):
r in the formula (2) is H, Cl, CN, NO2OR ', CONHR ' OR COOR '; wherein R' is H, CnH2n+1N is not less than 1 and not more than 18, and n is an integer;
wherein the structure of the dye C is structural formula (3):
r in the formula (3) is CH2CH3、CH2CH2CN or CH2COOR'; wherein R' is H or CnH2n+1N is not less than 1 and not more than 18, and n is an integer;
wherein the structure of the dye D is structural formula (4):
r in the formula (4) is CH2CH3、CH2CH2CN or CH2COOR ', wherein R' is H, CnH2n+1And n is an integer of not less than 1 and not more than 18.
The anthraquinone dye can be selected from at least one of dye E, dye F, dye G and dye H;
wherein the structure of the dye E is structural formula (5):
r in the formula (5)1Is H, Cl, CH3、OCH3、OC2H5、OH、NHR'、CN、CONH2、COOCH3Or COOC2H5；R2Is H, Cl, CH3、OCH3、OC2H5、OH、NHR'、CN、CONH2、COOCH3Or COOC2H5(ii) a Wherein R' is H, CnH2n+1And n is an integer of not less than 1 and not more than 18. X is OH or NH2(ii) a k is an integer of 1-3;
wherein the structure of the dye F is structural formula (6):
r in the formula (6)1Is H, Cl, CH3、OCH3、OC2H5、OH、NHR'、CN、CONH2、COOCH3Or COOC2H5；R2Is H, Cl, CH3、OCH3、OC2H5、OH、NHR'、CN、CONH2、COOCH3Or COOC2H5(ii) a Wherein R' is H, CnH2n+1And n is an integer of not less than 1 and not more than 18. X is OH or NH2(ii) a k is an integer of 1-3;
wherein the structure of the dye G is represented by the structural formula (7):
r in the formula (7)1Is H, Cl, CH3、OCH3、OC2H5、OH、NHR'、CN、CONH2、COOCH3Or COOC2H5；R2、R3H, Cl is,CH3、OCH3、OC2H5、OH、NHR'、CN、CONH2、COOCH3Or COOC2H5(ii) a Wherein R' is H, CnH2n+1And n is an integer of not less than 1 and not more than 18.
Wherein the structure of the dye H is structural formula (8):
r in the formula (8)1Is H, Cl, CH3、OCH3、OC2H5、OH、NHR'、CN、CONH2、COOCH3Or COOC2H5；R2、R3Is H, Cl, CH3、OCH3、OC2H5、OH、NHR'、CN、CONH2、COOCH3Or COOC2H5. Wherein R' is H, CnH2n+1And n is an integer of not less than 1 and not more than 18.
The invention also aims to provide a photothermal conversion polyurethane energy storage film. The film can be prepared by a method comprising the following steps: and pouring the photothermal conversion polyurethane energy storage film material into a polytetrafluoroethylene mold, and drying the mold to obtain the photothermal conversion polyurethane energy storage film.
According to the photothermal conversion polyurethane energy storage film, the dye is connected into the polyurethane, the dye and the shaping phase change material are organically combined through the covalent bond, the film with proper hardness can be prepared by adjusting the raw material ratio, the visible light of 380-780 nm in sunlight can be trapped and subjected to photothermal conversion by changing the variety of the dye, the energy is stored through the polyethylene glycol, and the light trapping, the photothermal conversion and the energy storage are realized. Compared with the traditional doping type, the film has good durability, and the compatibility and the stability are greatly improved. The prepared film has high phase transition enthalpy value, stable performance, relatively simple synthesis process and easily obtained raw materials, has wide application prospect, and can be used in the fields of intelligent clothing, food packaging, agricultural greenhouses and the like.
Drawings
FIG. 1 is a DSC curve of a photothermal conversion polyurethane energy storage film of example 9;
FIG. 2 is a graph showing an ultraviolet absorption spectrum of dye B in example 9;
FIG. 3 is a photothermal conversion curve of the photothermal conversion polyurethane energy storage thin film of example 9;
FIG. 4 is a DSC curve of the cyclic thermal stability test of example 9.
Detailed Description
The present invention will be further described with reference to the following examples. However, the present invention is not limited to these examples.
The experimental procedures shown in the following examples are, unless otherwise specified, conventional in the art; the reagents and materials are commercially available, unless otherwise specified.
And (3) treating polyethylene glycol and oligomer polyether or polyester diol in a vacuum drying oven at 60-80 ℃ for 2-3 h for later use.
Example 1
Adding 10g of polyethylene glycol 2000, 10g of polyester glycol PBA2000 and 40mL of N, N-Dimethylformamide (DMF) into a four-neck flask, introducing nitrogen, heating to 40-50 ℃ for dissolution, then cooling to 35 ℃, adding 5.5g of 4, 4' -diphenylmethane diisocyanate (MDI) dissolved in 40mLN, N-Dimethylformamide (DMF) into the flask, and reacting for 1-2 hours under heat preservation. Then, 0.13g of dye B, wherein R is H (structure shown in Table 1), dissolved in 20mL of N, N-Dimethylformamide (DMF) is added into the reaction system, and the temperature is raised to 65 ℃ for reaction for 1-2H. And finally, adding 1.2g of 1, 4-butanediol into the system, heating to 85 ℃ after the addition is finished, and continuously reacting for 2-3 h to obtain a polyurethane solution. And (3) putting 10mL of solution into a polytetrahydrofuran mold with the thickness of 15cm multiplied by 10cm multiplied by 1cm, and drying in a drying oven at 60 ℃ to obtain the photothermal conversion polyurethane energy storage film.
Example 2
The other contents of this embodiment are the same as embodiment 1, except that: the amount of polyethylene glycol 6000 was 9.6g, the amount of PBA2000 was 16.8g, the amount of dye B was 0.16g, and R ═ H in dye B (see table 1 for structure).
Example 3
The other contents of this embodiment are the same as embodiment 1, except that: the amount of polyethylene glycol 8000 was 13.6g, that of PBA2000 was 16.6g, and that of dye B was 0.16g, where R ═ H (structure see table 1).
Example 4
The other contents of this embodiment are the same as embodiment 1, except that: the amount of polyethylene glycol 10000 was 14g, PBA2000 was 17.2g, and dye B was 0.18g, where R ═ H (structure shown in table 1).
Example 5
The other contents of this embodiment are the same as embodiment 1, except that: the dosage of polyethylene glycol 20000 is 14g, the dosage of PBA2000 is 18.6g, the dosage of dye B is 0.16g, and R in the dye B is H (structure shown in Table 1).
Example 6
The other contents of this embodiment are the same as embodiment 1, except that: the amount of polyethylene glycol 10000 was 10g, PBA2000 was 6g, MDI was 3g, dye B was 0.09g, R ═ H (structure shown in table 1) in dye B, and 1, 4-butanediol was 0.8 g.
Example 7
The other contents of this embodiment are the same as embodiment 1, except that: the dosage of polyethylene glycol 10000 is 10g, the dosage of PBA2000 is 3g, the dosage of MDI is 3.13g, the dosage of dye B is 0.08g, R ═ H (structure shown in table 1) in dye B, and the dosage of 1, 4-butanediol is 1.0 g.
Example 8
The other contents of this embodiment are the same as embodiment 1, except that: the amount of polyethylene glycol 10000 was 10g, PBA2000 was 2g, MDI was 2g, dye B was 0.06g, R ═ H (structure shown in table 1) in dye B, and 1, 4-butanediol was 0.55 g.
Example 9
10g of polyethylene glycol 10000 is put into a four-necked flask, nitrogen is introduced, 40mL of DMF is added to be dissolved at 40-50 ℃, the temperature is reduced to 35 ℃ after the polyethylene glycol 10000 is completely dissolved, 1.75g of MDI is weighed to be dissolved in 20mL of DMF, the mixture is added into the flask at one time to react for 1-2H, 0.065g of dye B is dissolved in 20mL of DMF, wherein R is H, the mixture is added into the flask after the R is completely dissolved, the temperature is increased to 65 ℃, the reaction is carried out for 1-2H, finally 0.55g of 1, 4-butanediol is added, the temperature is increased to 85 ℃, the reaction is continued for 2-3H, a polyurethane solution is obtained, 10mL of the solution is put into a polytetrahydrofuran mold with the thickness of 15cm multiplied by 10cm by 1cm, the solvent is evaporated to dryness at 60 ℃ in a drying oven, and the photothermal conversion polyurethane energy storage film.
The melting and crystallization temperatures and enthalpy values of the materials were determined according to GB/T19466.3-2004 and the results are shown in FIG. 1.
The absorption wavelength of the dye solution was determined according to GB/T19267.2-2008 and the results are shown in FIG. 2.
According to the literature: the synthesis and performance research of the Wangming photo-thermal conversion polyether-based shape-stabilized phase change energy storage material [ D ]. university of great graduates, 2013. the photo-thermal conversion and energy storage capacity of the film are measured, and the results are shown in FIG. 3.
FIG. 4 is a DSC of a material before and after the material is repeatedly irradiated with simulated sunlight for 100 times.
As can be seen from figure 1, the enthalpy values of the temperature rise and the temperature drop of the material are 116.20J/g and 104.65J/g respectively, the phase transition temperatures are 65.89 ℃ and 24.39 ℃, which shows that the material has high energy storage density and can achieve the effects of storing and releasing heat.
As can be seen from FIG. 2, the maximum absorption wavelength of dye B is 504nm, and the maximum molar absorption coefficient of the dye is calculated to be 31449 L.mol according to the formula of the absorption law of light-1·cm-1The dye has higher absorption intensity to light.
As can be seen from FIG. 3, as the illumination time is prolonged, the temperature of the film gradually rises, reaches a temperature rise platform in about 15min, and rapidly drops after the light source is removed, but a temperature drop platform appears at about 25 ℃, which shows that the material converts light energy into heat energy and stores the heat energy by using phase change components, and after the material leaves the light source, the heat energy is slowly released to form a temperature drop platform.
As can be seen from fig. 4, after the material is subjected to 100 times of illumination cooling cycle experiments, the phase change enthalpy value of the material is reduced, but the whole phase change enthalpy value is not more than 10%, and the phase change temperature is not changed greatly, which indicates that the prepared photothermal conversion energy storage material has good stability.
Example 10
The other contents of this embodiment are the same as embodiment 9, except that: the dye is A (structure shown in Table 1), and the dosage of the dye is 0.069 g.
Example 11
The other contents of this embodiment are the same as embodiment 9, except that: the dye B (structure shown in Table 1) was used in an amount of 0.066 g.
Example 12
The other contents of this embodiment are the same as embodiment 9, except that: the dye is E (structure shown in Table 1), and the dosage of the dye is 0.065 g.
Example 13
The other contents of this embodiment are the same as embodiment 9, except that: the dye is F (structure shown in Table 1) and its amount is 0.063 g.
Table 1 specific structural formula of dye used in example
Claims (10)
1. The photothermal conversion polyurethane energy storage film material is characterized by having the following structural formula:
wherein: r is a diisocyanate component, R2Is oligomer diol component, Dye is Dye,
n＝2000～20000。
2. the preparation method of the photothermal conversion polyurethane energy storage thin film material according to claim 1, which is characterized by comprising the following steps:
(1) vacuum drying polyethylene glycol, low polymer polyether or polyester diol to remove water;
(2) dissolving the treated polyethylene glycol, oligomer polyether or polyester diol and diisocyanate in N, N-dimethylformamide, and reacting at 30-40 ℃ in a nitrogen atmosphere to obtain a polyurethane prepolymer;
(3) dissolving a dihydroxy dye in a solvent, adding the solvent into the polyurethane prepolymer, and raising the temperature to 60-70 ℃ for reaction; the solvent is selected from at least one of N, N-dimethylformamide, acetone or dichloromethane;
(4) and finally, adding a micromolecular diol chain extender, raising the temperature to 80-90 ℃ for reaction to obtain a polyurethane solution, namely the photothermal conversion polyurethane energy storage film material.
3. The preparation method of the photothermal conversion polyurethane energy storage thin film material as claimed in claim 2, wherein:
the molar ratio of the oligomer polyether or polyester diol to the polyethylene glycol is (0-15): 1, preferably (0 to 8): 1;
the molar ratio of the sum of the mole numbers of the polyethylene glycol, the oligomer polyether or the polyester diol to the small molecule diol is 1: (0.5 to 10), preferably 1: (0.7-5).
4. The preparation method of the photothermal conversion polyurethane energy storage thin film material as claimed in claim 2, wherein:
the molar ratio of the sum of hydroxyl groups in the polyethylene glycol, the oligomer polyether or the polyester diol to isocyanate groups in the diisocyanate is 1: (1 to 7), preferably 1: (2-5);
the molar ratio of the sum of hydroxyl groups in the polyethylene glycol, the oligomer polyether or polyester diol and the micromolecule diol to the isocyanate group in the diisocyanate is (1-2): 1, preferably (1 to 1.5): 1.
5. the photothermal conversion polyurethane energy storage thin film material of claim 2, wherein:
the molecular weight of the polyethylene glycol is 2000-20000, and is preferably 4000-10000;
the molecular weight of the oligomer polyether or polyester diol is 500-3000, preferably 1000-2500;
the diisocyanate is selected from at least one of 4, 4' -diphenylmethane diisocyanate, isophorone diisocyanate and toluene diisocyanate.
6. The photothermal conversion polyurethane energy storage thin film material of claim 2, wherein:
the oligomer polyether or polyester diol is at least one selected from polypropylene glycol, polytetrahydrofuran ether glycol, polybutylene adipate glycol and polyethylene adipate glycol;
the micromolecular dihydric alcohol is at least one selected from ethylene glycol, 1, 4-butanediol and 1, 6-hexanediol.
7. The photothermal conversion polyurethane energy storage thin film material of claim 2, wherein:
the using amount of the dihydroxy dye accounts for 0.1-3%, preferably 0.2-1% of the total mass of the polyethylene glycol, the oligomer polyether or polyester diol, the diisocyanate and the micromolecule diol;
the dihydroxy dye is azo dye or anthraquinone dye containing two active hydroxy groups.
8. The photothermal conversion polyurethane energy storage film material of claim 7, wherein:
the azo dye is selected from at least one of dye A, dye B, dye C and dye D;
wherein the structure of the dye A is structural formula (1):
in the formula (1), R is H, Cl, CN, NO2CONHR 'or COOR'; wherein R' is H, CnH2n+1N is not less than 1 and not more than 18, and n is an integer;
wherein the structure of the dye B is structural formula (2):
r in the formula (2) is H, Cl, CN, NO2OR ', CONHR ' OR COOR '; wherein R' is H, CnH2n+1N is not less than 1 and not more than 18, and n is an integer;
wherein the structure of the dye C is structural formula (3):
r in the formula (3) is CH2CH3、CH2CH2CN or CH2COOR'; wherein R' is H or CnH2n+1N is not less than 1 and not more than 18, and n is an integer;
wherein the structure of the dye D is structural formula (4):
r in the formula (4) is CH2CH3、CH2CH2CN or CH2COOR ', wherein R' is H, CnH2n+1And n is an integer of not less than 1 and not more than 18.
9. The photothermal conversion polyurethane energy storage film material of claim 7, wherein:
the anthraquinone dye is selected from at least one of dye E, dye F, dye G and dye H;
wherein the structure of the dye E is structural formula (5):
r in the formula (5)1Is H, Cl, CH3、OCH3、OC2H5、OH、NHR'、CN、CONH2、COOCH3Or COOC2H5；R2Is H, Cl, CH3、OCH3、OC2H5、OH、NHR'、CN、CONH2、COOCH3Or COOC2H5(ii) a Wherein R' is H, CnH2n+1N is not less than 1 and not more than 18, and n is an integer; x is OH or NH2(ii) a k is an integer of 1-3;
wherein the structure of the dye F is structural formula (6):
r in the formula (6)1Is H, Cl, CH3、OCH3、OC2H5、OH、NHR'、CN、CONH2、COOCH3Or COOC2H5；R2Is H, Cl, CH3、OCH3、OC2H5、OH、NHR'、CN、CONH2、COOCH3Or COOC2H5(ii) a Wherein R' is H, CnH2n+1N is not less than 1 and not more than 18, and n is an integer; x is OH or NH2(ii) a k is an integer of 1-3;
wherein the structure of the dye G is represented by the structural formula (7):
r in the formula (7)1Is H, Cl, CH3、OCH3、OC2H5、OH、NHR'、CN、CONH2、COOCH3Or COOC2H5；R2、R3Is H, Cl, CH3、OCH3、OC2H5、OH、NHR'、CN、CONH2、COOCH3Or COOC2H5(ii) a Wherein R' is H, CnH2n+1N is not less than 1 and not more than 18, and n is an integer;
wherein the structure of the dye H is structural formula (8):
r in the formula (8)1Is H, Cl, CH3、OCH3、OC2H5、OH、NHR'、CN、CONH2、COOCH3Or COOC2H5；R2、R3Is H, Cl, CH3、OCH3、OC2H5、OH、NHR'、CN、CONH2、COOCH3Or COOC2H5(ii) a Wherein R' is H, CnH2n+1And n is an integer of not less than 1 and not more than 18.
10. The photothermal conversion polyurethane energy storage thin film material according to claim 1 or the film made of the photothermal conversion polyurethane energy storage thin film material obtained by the preparation method according to any one of claims 2 to 9, characterized by being prepared by a method comprising the steps of: and pouring the photothermal conversion polyurethane energy storage film material into a polytetrafluoroethylene mold, and drying the mold to obtain the photothermal conversion polyurethane energy storage film.
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