CN101774964A - Synthesis of type of thermosensitive functionalized ion liquid - Google Patents
Synthesis of type of thermosensitive functionalized ion liquid Download PDFInfo
- Publication number
- CN101774964A CN101774964A CN200910243901A CN200910243901A CN101774964A CN 101774964 A CN101774964 A CN 101774964A CN 200910243901 A CN200910243901 A CN 200910243901A CN 200910243901 A CN200910243901 A CN 200910243901A CN 101774964 A CN101774964 A CN 101774964A
- Authority
- CN
- China
- Prior art keywords
- ion
- thermosensitive
- class
- temperature
- sensitive
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Landscapes
- Pyridine Compounds (AREA)
Abstract
The invention relates to a type of thermosensitive functionalized ion liquid. The type of thermosensitive functionalized ion liquid has the following structural general formula: A+B-, wherein, A+ is composed of cations such as pyridine; B- is composed of anions such as trifluoro-methyl-sulfamide ion (Tf2N-). The type of thermosensitive functionalized ion liquid is synthesized by neutralization reaction or ion exchange reaction. The novel ion liquid synthesized in the invention has available raw materials and low price and is easy to operate. The physical and chemical properties of the type of ion liquid change obviously along with change of temperature. The type of ion liquid can be used as thermosensitive materials such as thermosensitive paper, thermosensitive print, thermosensitive resistor, thermosensitive medium and the like, thermosensitive intelligentized control and thermosensitive pigment.
Description
Technical field:
The present invention relates generally to the synthetic and preparation of type of thermosensitive functionalized ion liquid, is mainly used in thermo-sensitive material, as: temperature-sensitive paper, temperature-sensitive printing, thermistor, thermal media etc., the intelligent control of temperature-sensitive, thermosensitive pigment may.
Background technology:
Ionic liquid is because advantages such as its difficult volatility, reusable edible, low pollution are considered green solvent, be widely used in fields such as separation, catalysis in recent years, also synthesized at present a large amount of functionalized ion liquids, but the temperature-sensitive functionalized ion liquid does not still have report so far, and the present invention has synthesized the temperature-sensitive functionalized ion liquid first.Synthetic novel ion liquid of the present invention, raw material conveniently is easy to get, and is cheap, and synthetic simple, easy handling.
Thermo-sensitive material is widely used in aspects such as thermo-paint, printing, textile garment in recent years, but a lot of thermo-sensitive materials are that temperature-sensitive is irreversible, temperature-sensitive ionic liquid among the present invention has the temperature-sensitive reversibility in certain temperature range, and temperature-sensitive indicated temperature wide ranges has better industrial application prospect.
The temperature-sensitive ionic liquid can be used as the surrogate of existing thermal recording medium.Thermal recording medium is widely used in facsimile printer system, various computer and other application scenario as recording medium.Development along with thermal recording medium, need the better more appearance of the thermo-sensitive material of best bright finish that has, existing thermal recording medium can not be satisfied the demand, as a kind of novel thermosensitive material, the temperature-sensitive ionic liquid has the advantage and the potential using value of himself uniqueness, its normal temperature majority down is liquid, can introduce needed various functional group to satisfy the requirement of thermal recording medium to smooth finish.In addition, the temperature-sensitive ionic liquid is made of zwitterion, has good electroconductibility, and for liquid has good flowability, the ion liquid flowability of the temperature-sensitive of some specific functions can vary with temperature and obvious variation takes place, and conductive capability also can change, be that variation has taken place resistance, this has just played the function of thermistor, and traditional thermal resistance does not have flowability, this advantage can be applied even more extensively in temperature-sensitive and be controlled automatically, senses variation of temperature by the variation that changes electric current, thereby the sensitivity of automatic control system is improved.Simultaneously, the temperature-sensitive ionic liquid also has very big using value in dyestuff, textile industry.
Because the temperature-sensitive ionic liquid has the advantage that many conventional thermo-sensitive materials do not possess, along with development of technology, the ion liquid potential using value of temperature-sensitive can be more and more obvious, the energy broader applications are in space flight, instrument, printing, weaving, food-processing, workers and peasants produce, and the temperature-sensitive ionic liquid that greater functionalityization can occur replaces existing heat-sensitive materials.
Summary of the invention:
The present invention designs and has synthesized type of thermosensitive functionalized ion liquid.
Ionic liquid among the present invention is by heterogeneous ring compound and derivatives thereof such as triarylmethane compound, Material of Fluoran, spiro-pyrans class, furans, pyridines, thiophene-based, Schiff bases, polymer class and derivative thereof and imidazoles, pyroles, pyrazoles, azole, thiazoles, indoles, pyrazine class, pyridazine class, quinoline, morpholine class, quinazoline ditosylate salt, piperazines, piperidines, oxazole class, oxazoline, oxazines classes, also comprises positively charged ion and chlorion (Cl such as quaternaries cation, phosphine class, ethers, aldehydes, ketone, hydro carbons, ester class and derivative thereof
-), bromide anion (Br
-), iodide ion (I
-), tetrafluoroborate ion (BF
4 -), hexafluorophosphoricacid acid ions (PF
6 -), trifluoromethyl sulphamide ion (Tf
2N
-), trifluoromethane sulfonic acid radical ion (CF
3SO
3 -), hexafluoro-antimonic acid radical ion (SbF
6 -), sulfate ion (SO
4 2-), carbonate (CO
3 2-), bicarbonate radical (HCO
3 -), nitrate ion (NO
3 -), carboxylate radical (RCOO
-) and fluoroform butyrate ion (CF
3CF
2CF
2CF
2SO
3 -) wait negatively charged ion to constitute, be liquid or solid state at normal temperatures.
Embodiment:
The present invention illustrates with following example, but the present invention is not limited to following examples, under the scope of described aim, changes and implements to be included in the technical scope of the present invention before and after not breaking away from.
Embodiment 1
Experimental installation is doubted pipe, mechanical stirrer and mercurythermometer by a four-hole boiling flask, returned cold and is formed.The 100.12g methyl ethyl diketone is dissolved in adds behind the 200mL dehydrated alcohol in the four-hole boiling flask, then 81.081g formaldehyde being mixed mutually with the 50mL dehydrated alcohol and insert in the dropping funnel, is 25% ammoniacal liquor with the 37.36mL massfraction and insert in the dropping funnel equally after the 25mL dehydrated alcohol mixes again.Open mechanical stirrer, under agitation formaldehyde solution and ammonia soln are slowly splashed in the methyl ethyl diketone solution, dripped off complete in 60 minutes with dropping funnel.And reacted temperature in the mercurythermometer Indicator Reaction device at normal temperatures and pressures 24 hours.With gained liquid 35 ℃ of dryings 40 hours in vacuum drying oven, obtain 3,5-diacetyl-1,4-dihydropyridine at last.Take by weighing 3.3022g (0.02mol) 3,5-diacetyl-1, the 4-dihydropyridine is inserted in the there-necked flask, and adds the 50mL dehydrated alcohol.Insert in the dropping funnel after taking by weighing the 4.3905g fluoroboric acid simultaneously and being dissolved in the 50mL dehydrated alcohol, open whipping appts, temperature of reaction is set is 35 ℃ and with a thermometer indicates temperature.After reaction was carried out 12 hours, vacuum rotary steam was removed the second alcohol and water in the product under 35 ℃ of conditions, at last with gained liquid in 35 ℃ in vacuum drying oven dry 24 hours, products therefrom is 3,5-diacetyl-1,4 dihydropyridine tetrafluoroborate ion liquid.Take by weighing an amount of 3,5-diacetyl-1,4-dihydropyridine tetrafluoroborate ion liquid is mixed with 1.0 * 10
-4The mol/L ethanolic soln is got this solution of 10mL then and is placed two 25mL colorimetric cylinders of A, B, respectively adds 2 saturated NaOH ethanolic solns in the colorimetric cylinder, and the A colorimetric cylinder is placed water-bath, and the B colorimetric cylinder places under the normal temperature and pressure conditions.A is heated to 40 ℃-100 ℃ respectively, and the temperature interval is 5 ℃, observes solution colour and changes, and the result shows A, and the liquid color difference is along with the rising of A colorimetric cylinder temperature becomes more and more obvious in B two colorimetric cylinders.
Embodiment 2
Experimental installation as above.Take by weighing 3.3022g (0.02mol) 3,5-diacetyl-1, the 4-dihydropyridine is inserted in the there-necked flask, and adds the 50mL dehydrated alcohol.Insert in the dropping funnel after taking by weighing 1.9189g hydrochloric acid simultaneously and being dissolved in the 50mL dehydrated alcohol, open whipping appts, temperature of reaction is set is 35 ℃ and with a thermometer indicates temperature.After reaction is carried out 12 hours; vacuum rotary steam is removed the second alcohol and water in the product under 35 ℃ of conditions, and with gained liquid under 35 ℃ in vacuum drying oven dry 24 hours, products therefrom was 3 at last; 5-diacetyl-1,4-dihydropyridine four hydrochloride ionic liquids.Take by weighing an amount of 3,5-diacetyl-1,4-dihydropyridine tetrafluoro hydrochloride ionic liquid is mixed with 1.0 * 10
-4The mol/L ethanolic soln is got this solution of 10mL then and is placed two 25mL colorimetric cylinders of A, B, respectively adds 2 saturated NaOH ethanolic solns in the colorimetric cylinder, and the A colorimetric cylinder is placed water-bath, and the B colorimetric cylinder places under the normal temperature and pressure conditions.A is heated to 40 ℃-100 ℃ respectively, and the temperature interval is 5 ℃, observes solution colour and changes, and the result shows A, and the liquid color difference is along with the rising of A colorimetric cylinder temperature becomes more and more obvious in B two colorimetric cylinders.
Embodiment 3
Experimental installation as above.Take by weighing 3.3022g (0.02mol) 3,5-diacetyl-1, the 4-dihydropyridine is inserted in the there-necked flask, and adds the 50mL dehydrated alcohol.Insert in the dropping funnel after taking by weighing 2.3059g phosphoric acid simultaneously and being dissolved in the 50mL dehydrated alcohol, open whipping appts, temperature of reaction is set is 35 ℃ and with a thermometer indicates temperature.After reaction was carried out 12 hours, vacuum rotary steam was removed the second alcohol and water in the product under 35 ℃ of conditions, and with gained liquid 35 ℃ of dryings 24 hours in vacuum drying oven, products therefrom is 3,5-diacetyl-1,4-dihydropyridine tetrafluoroborate ion liquid at last.Take by weighing an amount of 3,5-diacetyl-1,4-dihydropyridine phosphate ion liquid dosage becomes 1.0 * 10
-4The mol/L ethanolic soln is got this solution of 10mL then and is placed two 25mL colorimetric cylinders of A, B, respectively adds 2 saturated NaOH ethanolic solns in the colorimetric cylinder, and the A colorimetric cylinder is placed water-bath, and the B colorimetric cylinder places under the normal temperature and pressure conditions.A is heated to 40 ℃-100 ℃ respectively, and the temperature interval is 5 ℃, observes solution colour and changes, and the result shows A, and the liquid color difference is along with the rising of A colorimetric cylinder temperature becomes more and more obvious in B two colorimetric cylinders.
Claims (4)
1. type of thermosensitive functionalized ion liquid, such ionic liquid has following general structure: A
+B
-, A wherein
+It is a cationoid, be made of following material: heterogeneous ring compound and derivatives thereof such as triarylmethane compound, Material of Fluoran, spiro-pyrans class, furans, pyridines, thiophene-based, Schiff bases, polymer class and derivative thereof and imidazoles, pyroles, pyrazoles, azole, thiazoles, indoles, pyrazine class, pyridazine class, quinoline, morpholine class, quinazoline ditosylate salt, piperazines, piperidines, oxazole class, oxazoline, oxazines class also comprise quaternaries cation, phosphine class, ethers, aldehydes, ketone, hydro carbons, ester class and derivative thereof; Described B
-Be following negatively charged ion: chlorion (Cl
-), bromide anion (Br
-), iodide ion (I
-), tetrafluoroborate ion (BF
4 -), hexafluorophosphoricacid acid ions (PF
6 -), trifluoromethyl sulphamide ion (Tf
2N
-), trifluoromethane sulfonic acid radical ion (CF
3SO
3 -), hexafluoro-antimonic acid radical ion (SbF
6 -), sulfate ion (SO
4 2-), carbonate (CO
3 2-), bicarbonate radical (HCO
3 -), nitrate ion (NO
3 -), carboxylate radical (RCOO
-) and fluoroform butyrate ion (CF
3CF
2CF
2CF
2SO
3 -) in one or more.
2. temperature-sensitive functionalized ion liquid according to claim 1, it is active or have the group of temperature-sensitive function and mineral ions such as argentiferous, copper, mercury, cobalt, ferronickel, manganese in the grafting in ionic liquid in grafting on its ion that it has temperature-sensitive.
3. according to claim 1, the positively charged ion that a kind of temperature-sensitive ionic liquid is adopted can be A
+In one or more.
4. according to claim 1,2 described, such method for synthesizing ionic liquid is mainly finished by neutralization reaction and ion exchange reaction.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200910243901A CN101774964A (en) | 2009-12-25 | 2009-12-25 | Synthesis of type of thermosensitive functionalized ion liquid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200910243901A CN101774964A (en) | 2009-12-25 | 2009-12-25 | Synthesis of type of thermosensitive functionalized ion liquid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101774964A true CN101774964A (en) | 2010-07-14 |
Family
ID=42511578
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200910243901A Pending CN101774964A (en) | 2009-12-25 | 2009-12-25 | Synthesis of type of thermosensitive functionalized ion liquid |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101774964A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102250039A (en) * | 2011-05-16 | 2011-11-23 | 浙江大学 | Ionic liquid of N-methyl piperazine salt and preparation method thereof |
| CN108456780A (en) * | 2018-03-12 | 2018-08-28 | 沈阳农业大学 | A kind of method of ion liquid abstraction Cu in waste water ion |
| CN114518177A (en) * | 2022-02-14 | 2022-05-20 | 四川大学 | Glass thermometer based on eutectic composition of ionic liquid |
-
2009
- 2009-12-25 CN CN200910243901A patent/CN101774964A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102250039A (en) * | 2011-05-16 | 2011-11-23 | 浙江大学 | Ionic liquid of N-methyl piperazine salt and preparation method thereof |
| CN108456780A (en) * | 2018-03-12 | 2018-08-28 | 沈阳农业大学 | A kind of method of ion liquid abstraction Cu in waste water ion |
| CN114518177A (en) * | 2022-02-14 | 2022-05-20 | 四川大学 | Glass thermometer based on eutectic composition of ionic liquid |
| CN114518177B (en) * | 2022-02-14 | 2022-08-02 | 四川大学 | Glass thermometer based on eutectic composition of ionic liquid |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101774964A (en) | Synthesis of type of thermosensitive functionalized ion liquid | |
| CN101665677B (en) | Thermosensitive chromotropic material and manufacturing method and application thereof | |
| CN105646924A (en) | Monovalent anion selective ion exchange membrane and preparation method thereof | |
| CN105037062A (en) | Alcohol-based ternary deep-eutectic solvent and preparation method thereof | |
| CN105733554B (en) | A kind of reversible thermochromic composite and preparation method thereof | |
| CN104497710A (en) | New thermochromic ink | |
| CN105801595B (en) | The method that one kind catalysis prepares 4,5 dihydropyran [c] 1-benzopyran derivatives | |
| CN101538427A (en) | Temperature-sensing color-changing material and application thereof in electric kettle | |
| CN103145696B (en) | Organic ligand and metal organic frame based on Cu(II) ion, as well as synthesis method and application thereof | |
| CN111098374A (en) | Preparation method of reversible thermochromic functional wood | |
| CN105418511A (en) | 1-butyl-3-methylimidazole naphthoic formate ionic liquid and preparation method and application thereof | |
| CN106238098B (en) | A kind of preparation method and its catalyst for preparing of 1,2,4,5- tetra- substituted ramification of imidazole | |
| CN101688063B (en) | Aqueous synthesis of perylene pigments | |
| CN101162219A (en) | Pigment from mangrove kenaelia candel ph indicator | |
| CN106188937B (en) | A kind of compound liquid rare earth heat stabilizer | |
| CN101768433B (en) | Thermochromic organic cobalt phosphonate material Cox[R(PO3)m]y(H2O)z | |
| CN105820047A (en) | Three isomorphic complexes based on aromatic dicarboxylic acid ligand and synthesis method thereof | |
| CN108103582A (en) | A kind of low-temp reversible thermochromic crystals material, preparation method and the usage | |
| CN108559452A (en) | A kind of preparation method of phase-change thermal storage off-color material | |
| CN106188949B (en) | A kind of liquid-type rare earth complex heat stabilizer | |
| CN105622066B (en) | A kind of preparation method of micro emulsion-hydro-thermal method synthesis thermistor powder body material | |
| CN103951702B (en) | 1,1 '-dialkyl group-3, the preparation method of salt compound in 3 '-(2-phosphate-1,3-propylidene) imidazoles | |
| CN107827850A (en) | A kind of acid-base indicator and its preparation method and application | |
| CN103834220A (en) | Chromotropic paint | |
| PL89207B1 (en) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C12 | Rejection of a patent application after its publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20100714 |