CN106957384A - A kind of preparation method of the material of highly sensitive intelligent control humidity - Google Patents
A kind of preparation method of the material of highly sensitive intelligent control humidity Download PDFInfo
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- CN106957384A CN106957384A CN201710167306.XA CN201710167306A CN106957384A CN 106957384 A CN106957384 A CN 106957384A CN 201710167306 A CN201710167306 A CN 201710167306A CN 106957384 A CN106957384 A CN 106957384A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
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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
- C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
- C09K9/02—Organic tenebrescent materials
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- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
- D01D5/00—Formation of filaments, threads, or the like
- D01D5/0007—Electro-spinning
- D01D5/0015—Electro-spinning characterised by the initial state of the material
- D01D5/003—Electro-spinning characterised by the initial state of the material the material being a polymer solution or dispersion
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- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/28—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D01F6/36—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds comprising unsaturated carboxylic acids or unsaturated organic esters as the major constituent
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- D—TEXTILES; PAPER
- D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
- D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
- D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
- D04H1/70—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres characterised by the method of forming fleeces or layers, e.g. reorientation of fibres
- D04H1/72—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres characterised by the method of forming fleeces or layers, e.g. reorientation of fibres the fibres being randomly arranged
- D04H1/728—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres characterised by the method of forming fleeces or layers, e.g. reorientation of fibres the fibres being randomly arranged by electro-spinning
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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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/145—Heterocyclic containing oxygen as the only heteroatom
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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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/1466—Heterocyclic containing nitrogen as the only heteroatom
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Abstract
The invention discloses a kind of preparation method of the material of highly sensitive intelligent control humidity, comprise the following steps：The first step, synthesizes hydroxyethylindol；Second step, the synthesis of nitrogen ethoxy spiro-pyrans；3rd step, the synthesis of acrylated spiro-pyrans monomer；4th step, the synthesis of spiro-pyrans base co-polymer；5th step, electrostatic spinning prepares material.Intelligent adjustment humidity material prepared by a kind of preparation method of the material of highly sensitive intelligent control humidity of the present invention can under ultraviolet light or the moisture under dark condition in automatic storage air, then it is automatic by among water release to air again under visible light or when daytime, and sensitivity is very high, so as to reach the effect of Intelligent adjustment humidity.
Description
Technical field
The present invention relates to humidity regulation Material Field, especially a kind of preparation side of the material of highly sensitive intelligent control humidity
Method.
Background technology
Global warming and due to being located in inland and latitude, the central and west regions weather of Inner Mongolia Autonomous Region
Increasingly dry, desert distribution area accounts for 37.8% or so of the national desert gross area, tend to expansionization development.And the gas dried
Waiting can not only cause many places of human body function uncomfortable, such as mouth parched and tongue scorched, respiratory system immunity degradation, nose is bleeding, eye
It is astringent etc.；But also serious influence can be caused to the ecological environment of local or even surrounding cities.Therefore, research and develop a kind of
The new method and new material of effective regulation and control air humidity have more and more important meaning.
On humidity adjusting material, domestic and foreign scholars have carried out multifaceted research.At present, had a large amount of on humidity tune
The scientific achievement of material is saved, but most of researchs are main using the hygroscopicity of material as major function, lack to water release
Effective ways, and for controlling the exploitation of the intellectual material of suction-moisture releasing performance to be also rarely reported using environmental stimuli.Except this
In addition, most of methods and techniques for preparing hygroscopic material all have that step is various, technology of preparing is complicated, be unfavorable for realizing big face
The weak points such as product preparation are so as to be difficult to meet practical application.
The content of the invention
In order to overcome defect of the prior art, there is provided a kind of preparation method of the material of highly sensitive intelligent control humidity.
The present invention is realized by following proposal：
A kind of preparation method of the material of highly sensitive intelligent control humidity, comprises the following steps：
The first step, synthesizes hydroxyethylindol；
Second step, the synthesis of nitrogen ethoxy spiro-pyrans；
3rd step, the synthesis of acrylated spiro-pyrans monomer；
4th step, the synthesis of spiro-pyrans base co-polymer；
5th step, electrostatic spinning prepares material.
The first step comprises the following steps, by 2,3,3- tri-methyl indoles and ethylene bromohyrin according to molal weight ratio 1：1
Ratio be added in reaction dissolvent and reacted, flow back 12 hours, after reaction terminates, solvent evaporated, obtained solid
Product is washed repeatedly with absolute ether, finally gives white solid i.e. hydroxyethylindol.
In the first step, the reaction dissolvent is acetonitrile, and the evaporation is to be evaporated solvent using Rotary Evaporators.
The second step comprises the following steps, the hydroxyethylindol that the first step is synthesized and 5- nitrosalicylaldehydes and catalyst
Piperidines compares 1 with molal weight：1：1 ratio back flow reaction 3 hours in ethanol；
After reaction terminates, room temperature is cooled to, suction filtration, gained filter cake is washed with methanol, gained solid obtains nitrogen after drying
Ethoxy spiro-pyrans.
3rd step comprises the following steps, nitrogen ethoxy spiro-pyrans, acryloyl chloride and the triethylamine that second step is synthesized
Compare 1 with molal weight：1：1 ratio is reacted 12 hours using tetrahydrofuran as reaction dissolvent at 0 DEG C；
After reaction terminates, deionized water is added into reaction product and product is extracted with ethyl acetate, finally by gained
Extracted products carry out column chromatography purification.
The column chromatography purification is to use ethyl acetate：The molal weight ratio of petroleum ether is 1：4 mixture is used as expansion
Agent.
4th step comprises the following steps, the acrylated spiro-pyrans monomer and methyl methacrylate that the 3rd step is synthesized
Ester, azodiisobutyronitrile compare 1 with molal weight：9：0.5 ratio is added in dry DMF, at 60 DEG C
Lower reaction 24 hours；
After reaction terminates, room temperature is cooled to, and gained mixture is put into ethanol solution and suction filtration, suction filtration three is repeated
Secondary, it is spiro-pyrans base co-polymer that the solid of gained, which is dried,.
5th step comprises the following steps, and the spiro-pyrans base co-polymer that the 4th step is synthesized is dissolved in N, N- dimethyl formyls
In amine solvent, stirring makes polymer solution viscosity uniform for 12 hours, and solution then is carried out into electrostatic spinning, the membrane material of gained respectively
Material is intelligent humidifying material.
The mass percent of the spiro-pyrans base co-polymer in the solution is 25-45%.
The spinning distance of the electrostatic spinning is 15cm, and voltage is 15kV.
Beneficial effects of the present invention are：
Intelligent adjustment humidity material prepared by a kind of preparation method of the material of highly sensitive intelligent control humidity of the present invention
Can under ultraviolet light or the moisture under dark condition in automatic storage air, then under visible light or when daytime
It is automatic by among water release to air again, and sensitivity is very high, so as to reach the effect of Intelligent adjustment humidity.
Brief description of the drawings
Fig. 1 is the reaction scheme figure of spiro-pyrans base co-polymer of the present invention.
Embodiment
The preferred embodiment of the invention is further illustrated with reference to specific embodiment：
A kind of preparation method of the material of highly sensitive intelligent control humidity, comprises the following steps：
The first step, synthesizes hydroxyethylindol；
As shown in (1) in Fig. 1, the first step comprises the following steps, and 2,3,3- tri-methyl indoles and ethylene bromohyrin are pressed
Compare 1 according to molal weight：1 ratio, which is added in reaction dissolvent, is reacted, and is flowed back 12 hours, after reaction terminates, by solvent
Evaporate, obtained solid product is washed repeatedly with absolute ether, finally give white solid i.e. hydroxyethylindol.
In the first step, the reaction dissolvent is acetonitrile, and the evaporation is to be evaporated solvent using Rotary Evaporators.
As shown in (2) in Fig. 1, second step, the synthesis of nitrogen ethoxy spiro-pyrans；The second step comprises the following steps, will
The hydroxyethylindol of first step synthesis is with 5- nitrosalicylaldehydes and catalyst piperidines with molal weight ratio 1：1：1 ratio is in ethanol
Middle back flow reaction 3 hours；
After reaction terminates, room temperature is cooled to, suction filtration, gained filter cake is washed with methanol, gained solid obtains nitrogen after drying
Ethoxy spiro-pyrans.
As shown in (3) in Fig. 1, the 3rd step, the synthesis of acrylated spiro-pyrans monomer；3rd step includes following step
Suddenly, nitrogen ethoxy spiro-pyrans, acryloyl chloride and triethylamine second step synthesized is with molal weight ratio 1：1：1 ratio is with tetrahydrochysene
Furans is reaction dissolvent, is reacted 12 hours at 0 DEG C；
After reaction terminates, deionized water is added into reaction product and product is extracted with ethyl acetate, finally by gained
Extracted products carry out column chromatography purification.
The column chromatography purification is to use ethyl acetate：The molal weight ratio of petroleum ether is 1：4 mixture is used as expansion
Agent.
As shown in (3) in Fig. 1, the 4th step, the synthesis of spiro-pyrans base co-polymer；4th step comprises the following steps, will
The acrylated spiro-pyrans monomer and methyl methacrylate, azodiisobutyronitrile of 3rd step synthesis are with molal weight ratio 1：9：
0.5 ratio is added in dry DMF, is reacted 24 hours at 60 DEG C；
After reaction terminates, room temperature is cooled to, and gained mixture is put into ethanol solution and suction filtration, suction filtration three is repeated
Secondary, it is spiro-pyrans base co-polymer that the solid of gained, which is dried,.
5th step, electrostatic spinning prepares material.
5th step comprises the following steps, and the spiro-pyrans base co-polymer that the 4th step is synthesized is dissolved in N, N- dimethyl formyls
In amine solvent, stirring makes polymer solution viscosity uniform for 12 hours, and solution then is carried out into electrostatic spinning, the membrane material of gained respectively
Material is intelligent humidifying material.The mass percent of the spiro-pyrans base co-polymer in the solution is 25-45%.The Static Spinning
The spinning distance of silk is 15cm, and voltage is 15kV.
The present invention realizes the preparation of material substrate using electrostatic spinning technique, and Electrospinning is simple, easy to operate, cost
It is low, and suitable for the production of large area material, it has also become a kind of effective side for preparing surface roughness and morphology controllable material
Method.And electrical spinning method can prepare the tunica fibrosa of porous easily there is provided sufficient water space, be effectively
Adjust humidity and basic condition is provided.And what the Intelligent adjustment of humidity mainly used spiro-pyrans organic molecule to realize.Spiro-pyrans
Class compound is the photosensitive organic compound that a class receives much concern, also most representative.Spiro-pyrans class compound is in different wave length
Light excites lower generation C-O keys to be broken and cause the structure change of open loop-closed loop, when the surface for being connected with spiro-pyrans class compound (SP)
When material is by ultraviolet light, the C-O keys fracture in molecule on loop coil is changed into polar molecule, generates the merocyanine of open loop
Compound (MC), the merocyanine compound can be with bivalent metal ion, H+, amino acid and DNA are combined causes the movement of absorption spectrum
And then realize corresponding color change；And C-O keys are reconnected after radiation of visible light, the closed loop molecule of nonpolar state is become again simultaneously
Recover original color.Such photosensitive organic compound has sensitivity higher, fast to ultraviolet-sensitive and electron transfer speed
The features such as.Reversible transition between polarity can occur under ultraviolet-visible light irradiation and be nonpolar due to spiro-pyrans molecule, and then
Occurs the change of wetability, so such photosensitive organic molecule can realize the intelligent control to humidity.
The effect of the present invention is further detailed with four specific embodiments below.
(1) spiro-pyrans base co-polymer is dissolved in DMF solvent with the ratio that mass ratio is respectively 35%
In, stirring makes polymer solution viscosity uniform in 12 hours.These solution are then subjected to electrostatic spinning respectively, spinning distance is
15cm, voltage is 15kV.
Resulting membrane material is pale red, and the fiber group for finding that material is about 2 μm by diameter is amplified by ESEM
Into ultra violet lamp 15 minutes, its surface contact angle reduces 8 °, humidity reduction by 6%.15 points are irradiated to it with visible ray again
Clock, contact angle and humidity return to original numerical value, are repeated 5 times and obtain same result.The membrane area and mould tested
It is 1.6m to intend spatial volume ratio2/m3。
(2) spiro-pyrans base co-polymer is dissolved in DMF solvent with the ratio that mass ratio is respectively 30%
In, stirring makes polymer solution viscosity uniform in 12 hours.These solution are then subjected to electrostatic spinning respectively, spinning distance is
15cm, voltage is 15kV.
Resulting membrane material is pale red, finds that material is about 1.7 μm of fiber groups by diameter by ESEM amplification
Into ultra violet lamp 15 minutes, its surface contact angle reduces 14 °, humidity reduction by 10%.15 points are irradiated to it with visible ray again
Clock, contact angle and humidity return to original numerical value, are repeated 5 times and obtain same result.The membrane area and mould tested
It is 1.6m to intend spatial volume ratio2/m3。
(3) spiro-pyrans base co-polymer is dissolved in DMF solvent with the ratio that mass ratio is respectively 25%
In, stirring makes polymer solution viscosity uniform in 12 hours.These solution are then subjected to electrostatic spinning respectively, spinning distance is
15cm, voltage is 15kV.
Resulting membrane material be pale red, by ESEM amplify find material by a diameter of 500nm fiber and
2.5-5.0 μm of microballoon composition, ultra violet lamp 15 minutes, its surface contact angle reduces 23 °, humidity reduction by 15%.Use again
Visible ray irradiates 15 minutes to it, and contact angle and humidity return to original numerical value, are repeated 5 times and obtain same result.
The membrane area tested is 1.6m with simulation spatial volume ratio2/m3。
In summary, the intelligence tune prepared by a kind of preparation method of the material of highly sensitive intelligent control humidity of the invention
Save humidity material can under ultraviolet light or the moisture under dark condition in automatic storage air, then under visible light or
It is automatic by among water release to air again when daytime, and sensitivity is very high, so as to reach the work of Intelligent adjustment humidity
With.
Although having done more detailed elaboration to technical scheme and having enumerated, it will be appreciated that for ability
For field technique personnel, modification is made to above-described embodiment or equivalent alternative solution is used, this is to those skilled in the art
It is it is clear that these modifications or improvements without departing from theon the basis of the spirit of the present invention, belong to the present invention for member
Claimed scope.
Claims (10)
1. a kind of preparation method of the material of highly sensitive intelligent control humidity, it is characterised in that comprise the following steps：
The first step, synthesizes hydroxyethylindol；
Second step, the synthesis of nitrogen ethoxy spiro-pyrans；
3rd step, the synthesis of acrylated spiro-pyrans monomer；
4th step, the synthesis of spiro-pyrans base co-polymer；
5th step, electrostatic spinning prepares material.
2. a kind of preparation method of the material of highly sensitive intelligent control humidity according to claim 1, it is characterised in that：Institute
State the first step to comprise the following steps, by 2,3,3- tri-methyl indoles and ethylene bromohyrin according to molal weight ratio 1：1 ratio is added
Reacted, flowed back 12 hours into reaction dissolvent, after reaction terminates, solvent is evaporated, obtained solid product is with anhydrous
Ether washing is multiple, finally gives white solid i.e. hydroxyethylindol.
3. a kind of preparation method of the material of highly sensitive intelligent control humidity according to claim 2, it is characterised in that：
In the first step, the reaction dissolvent is acetonitrile, and the evaporation is to be evaporated solvent using Rotary Evaporators.
4. a kind of preparation method of the material of highly sensitive intelligent control humidity according to claim 1, it is characterised in that：Institute
Second step is stated to comprise the following steps, the hydroxyethylindol that the first step is synthesized and 5- nitrosalicylaldehydes and catalyst piperidines with mole
Mass ratio 1：1：1 ratio back flow reaction 3 hours in ethanol；
After reaction terminates, room temperature is cooled to, suction filtration, gained filter cake is washed with methanol, gained solid obtains nitrogen hydroxyl second after drying
Base spiro-pyrans.
5. a kind of preparation method of the material of highly sensitive intelligent control humidity according to claim 1, it is characterised in that：Institute
State the 3rd step to comprise the following steps, nitrogen ethoxy spiro-pyrans, acryloyl chloride and the triethylamine that second step is synthesized are with molal weight
Than 1：1：1 ratio is reacted 12 hours using tetrahydrofuran as reaction dissolvent at 0 DEG C；
After reaction terminates, deionized water is added into reaction product and product is extracted with ethyl acetate, finally by the extraction of gained
Product carries out column chromatography purification.
6. a kind of preparation method of the material of highly sensitive intelligent control humidity according to claim 5, it is characterised in that：Institute
It is to use ethyl acetate to state column chromatography purification：The molal weight ratio of petroleum ether is 1：4 mixture is used as solvent.
7. a kind of preparation method of the material of highly sensitive intelligent control humidity according to claim 1, it is characterised in that：Institute
State the 4th step to comprise the following steps, the acrylated spiro-pyrans monomer and methyl methacrylate, azo two that the 3rd step is synthesized
Isobutyronitrile compares 1 with molal weight：9：0.5 ratio is added in dry DMF, and 24 are reacted at 60 DEG C
Hour；
After reaction terminates, room temperature is cooled to, and gained mixture is put into ethanol solution and suction filtration, suction filtration is repeated three times,
It is spiro-pyrans base co-polymer that the solid of gained, which is dried,.
8. a kind of preparation method of the material of highly sensitive intelligent control humidity according to claim 1, it is characterised in that：Institute
State the 5th step to comprise the following steps, the spiro-pyrans base co-polymer that the 4th step is synthesized is dissolved in DMF solvent,
Stirring makes polymer solution viscosity uniform for 12 hours, solution then is carried out into electrostatic spinning respectively, the membrane material of gained is intelligence
Can humidity adjusting material.
9. a kind of preparation method of the material of highly sensitive intelligent control humidity according to claim 8, it is characterised in that：Institute
The mass percent of spiro-pyrans base co-polymer in the solution is stated for 25-45%.
10. a kind of preparation method of the material of highly sensitive intelligent control humidity according to claim 8, it is characterised in that：
The spinning distance of the electrostatic spinning is 15cm, and voltage is 15kV.
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| US20100119761A1 (en) * | 2006-11-28 | 2010-05-13 | Arkema France | Optical 3d memory comprising a block copolymer containing a photoactive monomer having a photoisomerable group |
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