CN105131271A - Poly ionic liquid type alkaline indicator suitable for non-polar solvents, and preparation thereof - Google Patents
Poly ionic liquid type alkaline indicator suitable for non-polar solvents, and preparation thereof Download PDFInfo
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Abstract
The present invention provides a poly ionic liquid type alkaline indicator suitable for non-polar solvents, and a preparation method thereof. The preparation method is characterized by comprising: carrying out water and oxygen removing treatment on a reaction container; under nitrogen protection, adding o-phthalic anhydride and N,N-dimethylformamide to the reaction container; under nitrogen protection, adding ethylene glycol, and stirring; adding epichlorohydrin to the obtained solution, and carrying out a reaction under stirring; adding N-methylimidazole, and carrying out a reaction under stirring; adding the obtained mixture to acetone, stirring, and precipitating; dissolving the precipitate in deionized water, adding to a methyl blue aqueous solution in a dropwise manner, carrying out a reaction under stirring, and precipitating; repeatedly rinsing the obtained precipitate with deionized water, carrying out vacuum drying, adding to methylene chloride, and stirring to form a mixture; and filtering to obtain a filtrate, and carrying out vacuum drying to obtain the poly ionic liquid type alkaline indicator suitable for non-polar solvents. The polymer of the present invention can be used in the alkaline indication field of the non-polar solvents.
Description
Technical field
The present invention relates to a kind of basic indicator of chemical technology field, specifically, that relate to is a kind of preparation method in non-polar solvent with the poly ion liquid type indicator of alkaline deixis.
Background technology
Ionic liquid is a kind of in room temperature or close to the ionic compound be in a liquid state under room temperature.Before 100 years, ionic liquid is reported for the first time, and the application of ionic liquid covers numerous areas, as fine chemistry industry, separating-purifying, electrochemistry, solar cell, bio-medical etc.In recent years, the poly ion liquid developed by ionic liquid has attracted huge concern at polymer chemistry and material science.Poly ion liquid is the polymkeric substance on repeating unit with anions and canons electrolyte group.Poly ion liquid have ionic liquid low melting point, low-vapor pressure, good conductivity, good stability, recyclable, nontoxic pollution-free good characteristic and main polymer chain mechanical stability is good, processability is good, chemical compatibility is good, good endurance, excellent properties that space manipulative capability is strong.More than that, poly ion liquid has more very excellent ion interchangeability, by simple ion-exchange, can prepare large quantities of novel functional poly ionic liquid.The application of poly ion liquid is increasingly extensive, as dispersion agent, consisting of phase-transferring agent, sorbent material, separating agent, ion conductive material, nano composite material, bio-medical material etc.
The poly ion liquid type basic indicator being applicable to non-polar solvent refers to that in non-polar solvent (as methylene dichloride), have alkali causes variable color to reach the novel poly ion liquid of deixis.Original water soluble anion indicator (as Methylene blue) can only water-soluble and these polar solvents of methyl alcohol, even if the current research to poly ion liquid type basic indicator also mainly concentrates in the aqueous solution, methyl alcohol, these polar solvent environment of acetone, and there is not been reported to the poly ion liquid in non-polar solvent with alkaline deixis.Therefore how to utilize commercialization raw material, adopting simple method to prepare the poly ion liquid type basic indicator being applicable to non-polar solvent, will be very meaningful.
Through finding the literature search of prior art, poly ion liquid type basic indicator is able to preparation mainly through repeating unit deixis group being connected to main polymer chain and completes.The people such as JiangnaGuo have delivered " PlasticreusablepHindicatorstrips:preparationviaanion-exc hangeofpoly (ionicliquids) withanionicdyes " (by carrying out with anionic dyestuff the plasticity pH test paper that can be used repeatedly that anionresin prepares) " PolymerChemistry " the 4th volume in 2013 the 1309th page to 1312 pages, first this article author has synthesized cross-linked polymer, the polymkeric substance pH test paper that dye molecule not easily reveals has been synthesized utilizing with anionic dyestuff anionresin, it all has good alkaline indicating effect in the aqueous solution and some polar organic solvents.Owing to being still in the stage of development to the research of poly ion liquid basic indicator, the poly ion liquid type basic indicator being therefore specially adapted for non-polar solvent does not appear in the newspapers so far.
Summary of the invention
The object of the invention is to the suitable solvents scope opening up poly ion liquid type basic indicator, use molecular designing, obtain a kind of solvable and there is the poly ion liquid type basic indicator of alkaline deixis in non-polar solvent.
The present invention is achieved by the following technical solutions, the present invention take ethylene glycol as initiator, Tetra hydro Phthalic anhydride and epoxy chloropropane monomer are raw material, utilize alternately ring-opening polymerization, synthesis is such as formula the linear polyester shown in (1), then N-Methylimidazole is grafted to polyester repeating unit, prepare such as formula the linear poly ion liquid (PIL-Cl) shown in (2), finally utilize PIL-Cl and Methylene blue group generation ion-exchange, thus to prepare such as formula the negatively charged ion shown in (3) be the linear poly ion liquid PIL-MB of Methylene blue.
Concrete technical scheme of the present invention is:
Be applicable to a poly ion liquid type basic indicator for non-polar solvent, it is characterized in that, its structural formula is as follows:
Wherein, n is 10-50.
The above-mentioned preparation method being applicable to the poly ion liquid type basic indicator of non-polar solvent, is characterized in that, comprise the following steps:
Step a: reaction vessel is dewatered deoxygenation process;
Step b: add Tetra hydro Phthalic anhydride and DMF under nitrogen protection in reaction vessel, stirs the DMF solution obtaining Tetra hydro Phthalic anhydride;
Step c: add ethylene glycol under nitrogen protection in the DMF solution of the Tetra hydro Phthalic anhydride in step b, stirs;
Steps d: epoxy chloropropane is joined in the solution that step c obtains, under agitation react;
Step e: remaining epoxy chloropropane in the mixture be obtained by reacting in removing step d, adds N-Methylimidazole, under agitation react;
Step f: the mixture be obtained by reacting in step e is added in acetone, stir, solid-liquid separation is precipitated;
Step g: by the resolution of precipitate that obtains in step f in deionized water, be added drop-wise in the Methylene blue aqueous solution, under agitation react, solid-liquid separation is precipitated;
Step h: the precipitate with deionized water obtained in step g repeatedly rinsed, vacuum-drying, joins in methylene dichloride, stirs and forms mixture.
Step I: filtered by the mixture obtained in step h, obtain filtrate, rotary evaporation removing dichloromethane solvent, vacuum-drying, obtains the poly ion liquid type basic indicator being applicable to non-polar solvent.
Preferably, the concentration of the DMF solution of the Tetra hydro Phthalic anhydride in described step b is 0.1-1 grams per milliliter.
Preferably, in described step c, the molecular fraction that described ethylene glycol accounts for Tetra hydro Phthalic anhydride is 1%-2%.
Preferably, in described steps d, described epoxy chloropropane and the mol ratio of Tetra hydro Phthalic anhydride are 1-1.3: 1.
Preferably, in described steps d, react under described stirring, its temperature is 95-120 DEG C, and its reaction times is 10-12 hour.
Preferably, the mol ratio of the Tetra hydro Phthalic anhydride in the DMF solution of the Tetra hydro Phthalic anhydride in the N-Methylimidazole added in described step e and step b is 1.1-1.5: 1.
Preferably, in described step e, react under described stirring, its temperature of reaction is 80-95 DEG C, and its reaction times is 4-6 days.
Preferably, in described step f, the volume ratio of the mixture obtained in described acetone and step e is 9-13: 1.
Preferably, in described step g, in described tropeolin-D and step f, the mol ratio of the TMSIM N imidazole group that gained precipitates in (PIL-Cl) is 1.2-1.8: 1.
Preferably, in described step g, react under described stirring, its temperature of reaction is 5-25 DEG C, and its reaction times is 10-20 hour.
Preferably, in described step h, described whipping temp is 5-40 DEG C, and its time is 5-10 hour.
Preferably, the precipitation in described step h after vacuum-drying and the ratio of methylene dichloride are 1g: 0.05-1L.
Principle of the present invention is the ring-opening reaction utilizing initiator ethylene glycol elder generation and Tetra hydro Phthalic anhydride generation acid anhydrides, acid anhydrides open-loop products and epoxy chloropropane carry out the ring-opening reaction of epoxy, epoxy addition product carries out the ring-opening reaction of acid anhydrides with Tetra hydro Phthalic anhydride again, repeated open loop is reacted, obtain polyester product, then by graft reaction, N-Methylimidazole is connected to polyester repeating unit, obtain the poly ion liquid PIL-Cl that negatively charged ion is chlorion, ion-exchange is carried out finally by tropeolin-D group and chlorion group, tropeolin-D group is connected on N-Methylimidazole group, prepare the poly ion liquid type basic indicator being applicable to non-polar solvent.The molecular structure that gained is applicable to the poly ion liquid type basic indicator of non-polar solvent can be measured by nuclear magnetic resonance spectrum.The alkaline deixis of poly ion liquid type basic indicator in non-polar solvent is measured by ultraviolet-visible pectrophotometer.And infrared spectra, gel permeation chromatography, differential scanning calorimetry, thermal weight loss etc. can be used as assistant analysis means.
The poly ion liquid type basic indicator being applicable to non-polar solvent prepared in accordance with the present invention, its low in raw material price, synthesizes easy, and reaction controllability is good.This polymkeric substance has good thermostability, can demonstrate obvious alkaline deixis in non-polar solvent.In view of it has good solvability and obvious alkaline indication action in non-polar solvent, this polymkeric substance can be used for the alkalescence instruction field in non-polar solvent.
Accompanying drawing explanation
Fig. 1 is the nuclear magnetic spectrogram being applicable to the poly ion liquid type basic indicator of non-polar solvent prepared by the present invention;
Wherein: figure a, b, c respectively corresponding embodiment 1, example 2, example 3 prepare the one dimension nucleus magnetic hydrogen spectrum collection of illustrative plates being applicable to the poly ion liquid type basic indicator of non-polar solvent.
Fig. 2 is the differential scanning calorimetry figure being applicable to the poly ion liquid type basic indicator of non-polar solvent prepared by the present invention.
Fig. 3 is the solvability test photo being applicable to the poly ion liquid type basic indicator of non-polar solvent prepared by the present invention.
Fig. 4 is the alkalescence instruction photo of the poly ion liquid type basic indicator being applicable to non-polar solvent under different Isopropylamine concentration prepared by the present invention.
Fig. 5 is the ultraviolet-visible spectrogram of poly ion liquid type basic indicator under different Isopropylamine concentration being applicable to non-polar solvent prepared by the present invention.
Fig. 6 is the hot weightless picture being applicable to the poly ion liquid type basic indicator of non-polar solvent prepared by the present invention.
Fig. 7 molecule measuring test result that to be the poly ion liquid type basic indicator being applicable to non-polar solvent prepared of embodiment 1-3 record through gel permeation chromatography and corresponding n value.
Embodiment
Below embodiments of the invention are elaborated: this example is implemented under premised on technical solution of the present invention, give detailed embodiment and concrete operating process, but protection scope of the present invention is not limited to following embodiment.
Embodiment 1
Be applicable to a poly ion liquid type basic indicator for non-polar solvent, its structural formula is such as formula shown in (3), and wherein, n is 18.
The above-mentioned preparation method being applicable to the poly ion liquid type basic indicator of non-polar solvent is:
Step a: to dewater deoxygenation process to 150 milliliters of there-necked flasks, the described deoxygenation that dewaters is treated to: fully dried 3 hours under 90 degrees Celsius by 150 of cleaning milliliters of there-necked flasks, takes out and is cooled to room temperature, pass into nitrogen;
Step b: under nitrogen protection, adds 29.60 grams of Tetra hydro Phthalic anhydrides and 50 milliliters of DMFs in there-necked flask, stirs and forms homogeneous solution;
Step c: add 0.13 gram of ethylene glycol (molecular fraction accounting for Tetra hydro Phthalic anhydride is molecular fraction 1%) in the solution obtained to step b under nitrogen protection, stirs;
Steps d: add 18.50 grams of epoxy chloropropane in the solution that step c obtains, carries out reaction 10 hour under stirring at 105 DEG C;
Step e: remaining epoxy chloropropane in the mixture adopting vacuumizing method removing step d to obtain, adds 24.63 grams of N-Methylimidazoles, carries out reaction 4 day under stirring at 90 DEG C;
Step f: added by the mixture obtained in step e (volume ratio of mixture and acetone is 1: 10) in acetone, stirs, and adopts the method for filtering to carry out solid-liquid separation and is precipitated;
Step g: by the resolution of precipitate that obtains in 0.34 gram of step f in 50 ml deionized water, slowly be added drop-wise in the Methylene blue aqueous solution containing 1 gram of Methylene blue and 400 ml deionized water, carry out reaction 15 hours under stirring at 10 DEG C, adopt the method for filtering to carry out solid-liquid separation and be precipitated;
Step h: the precipitate with deionized water obtained in step g repeatedly rinsed, vacuum-drying, obtains 0.62 gram of precipitation, joins in 150 milliliters of methylene dichloride, stirs 5 hours, obtain mixture at 20 DEG C.
Step I: filtered by the mixture obtained in step h, obtain filtrate, rotary evaporation removing dichloromethane solvent, vacuum-drying, obtains the poly ion liquid type basic indicator being applicable to non-polar solvent.
Embodiment 2
Be applicable to a poly ion liquid type basic indicator for non-polar solvent, its structural formula is such as formula shown in (3), and wherein, n is 21.
The above-mentioned preparation method being applicable to the poly ion liquid type basic indicator of non-polar solvent is:
Step a: to dewater deoxygenation process to 150 milliliters of there-necked flasks, the described deoxygenation that dewaters is treated to: fully dried 3 hours under 90 degrees Celsius by 150 of cleaning milliliters of there-necked flasks, takes out and is cooled to room temperature, pass into nitrogen;
Step b: under nitrogen protection, adds 27.00 grams of Tetra hydro Phthalic anhydrides and 50 milliliters of DMFs in there-necked flask, stirs and forms homogeneous solution;
Step c: add 0.18 gram of ethylene glycol (accounting for the molecular fraction 1.5% of Tetra hydro Phthalic anhydride) in the solution obtained to step b under nitrogen protection, stirs;
Steps d: add 16.88 grams of epoxy chloropropane in the solution that step c obtains, carries out reaction 10 hour under stirring at 100 DEG C;
Step e: remaining epoxy chloropropane in the mixture adopting vacuumizing method removing step d to obtain, adds 25 grams of N-Methylimidazoles, carries out reaction 4 day under stirring at 90 DEG C;
Step f: added by the mixture obtained in step e (volume ratio of mixture and acetone is 1: 10) in acetone, stirs, and adopts the method for filtering to carry out solid-liquid separation and is precipitated;
Step g: by the resolution of precipitate that obtains in 0.4 gram of step f in 50 ml deionized water, slowly be added drop-wise in the Methylene blue aqueous solution containing 1.2 grams of Methylene blues and 400 ml deionized water, carry out reaction 15 hours under stirring at 15 DEG C, adopt the method for filtering to carry out solid-liquid separation and be precipitated;
Step h: the precipitate with deionized water obtained in step g repeatedly rinsed, vacuum-drying, obtains 0.74 gram, joins in 150 milliliters of methylene dichloride, stirs 6 hours, obtain mixture at 20 DEG C.
Step I: filtered by the mixture obtained in step h, obtain filtrate, rotary evaporation removing dichloromethane solvent, vacuum-drying, obtains the poly ion liquid type basic indicator being applicable to non-polar solvent.
Embodiment 3
Be applicable to a poly ion liquid type basic indicator for non-polar solvent, its structural formula is such as formula shown in (3), and wherein, n is 25.
The above-mentioned preparation method being applicable to the poly ion liquid type basic indicator of non-polar solvent is:
Step a: to dewater deoxygenation process to 150 milliliters of there-necked flasks, the described deoxygenation that dewaters is treated to: fully dried 3 hours under 90 degrees Celsius by 150 of cleaning milliliters of there-necked flasks, takes out and is cooled to room temperature, pass into nitrogen;
Step b: under nitrogen protection, adds 30.00 grams of Tetra hydro Phthalic anhydrides and 50 milliliters of DMFs in there-necked flask, stirs and forms homogeneous solution;
Step c: add 0.2 gram of ethylene glycol (accounting for the molecular fraction 1.5% of Tetra hydro Phthalic anhydride) in the solution obtained to step b under nitrogen protection, stirs;
Steps d: add 18.75 grams of epoxy chloropropane in the solution that step c obtains, carries out reaction 10 hour under stirring at 100 DEG C;
Step e: remaining epoxy chloropropane in the mixture adopting vacuumizing method removing step d to obtain, adds 25 grams of N-Methylimidazoles, carries out reaction 5 day under stirring at 90 DEG C;
Step f: added by the mixture obtained in step e (volume ratio of mixture and acetone is 1: 10) in acetone, stirs, and adopts the method for filtering to carry out solid-liquid separation and is precipitated;
Step g: by the resolution of precipitate that obtains in 0.3 gram of step f in 50 ml deionized water, slowly be added drop-wise in the Methylene blue aqueous solution containing 0.9 gram of Methylene blue and 400 ml deionized water, carry out reaction 20 hours under stirring at 20 DEG C, adopt the method for filtering to carry out solid-liquid separation and be precipitated;
Step h: the precipitate with deionized water obtained in step g repeatedly rinsed, vacuum-drying, obtains 0.58 gram of precipitation, joins in 150 milliliters of methylene dichloride, stirs 7 hours, obtain mixture at 20 DEG C.
Step I: filtered by the mixture obtained in step h, obtain filtrate, rotary evaporation removing dichloromethane solvent, vacuum-drying, obtains the poly ion liquid type basic indicator being applicable to non-polar solvent.
Embodiment the results are shown in accompanying drawing:
Fig. 1 a, 1b, 1c respectively corresponding embodiment 1, example 2, example 3 prepare the one dimension nucleus magnetic hydrogen spectrum collection of illustrative plates being applicable to the poly ion liquid type basic indicator of non-polar solvent, wherein the peak at 3.84ppm place is the chemical shift of the primary carbon proton that imidazole group is connected with nitrogen; The peak at 4.67ppm place is the chemical shift of the secondary carbon proton be connected with ester group; The peak at 5.72ppm place is the chemical shift of the tertiary carbon proton that ester group is connected; The multiplet at 7ppm-8ppm place is the chemical shift of proton on phenyl ring and imidazole ring; 9.17ppm place unimodal is the chemical shift of the secondary carbon proton that imidazole ring is connected respectively with two nitrogen.Meanwhile, it has fignal center strongly within the scope of 1-1.5ppm, and the 1HNMR spectrogram of polyester and PIL-Cl is then presented within the scope of 1-1.5ppm without clear signal peak.In addition, all there is the fignal center corresponding with Methylene blue nuclear-magnetism at 7.02ppm, 7.28ppm, 7.54ppm etc.This demonstrate that the successful preparation of the poly ion liquid type basic indicator being applicable to non-polar solvent.
The differential scanning calorimetry spectrogram being applicable to the poly ion liquid type basic indicator of non-polar solvent prepared by the corresponding embodiment 1 of Fig. 2.
The solvability being applicable to the poly ion liquid type basic indicator of non-polar solvent prepared by the corresponding embodiment 1 of Fig. 3 tests photo.This figure shows that this polymkeric substance is insoluble to upper strata aqueous phase, and is only dissolved in lower floor's methylene dichloride phase.Can illustrate that this polymkeric substance changes the water-soluble of Methylene blue completely accordingly, then be dissolved in non-polar solvent.
The alkalescence instruction photo of the poly ion liquid type basic indicator being applicable to non-polar solvent under different Isopropylamine concentration prepared by the corresponding embodiment 1 of Fig. 4.This figure shows that the dichloromethane solution of this polymkeric substance is become colorless by blueness gradually when Isopropylamine concentration increases to 2.1mol/L from 0mol/L.Can illustrate that this polymkeric substance has fairly obvious alkaline deixis in non-polar solvent accordingly.
The ultraviolet-visible spectrogram of poly ion liquid type basic indicator under different Isopropylamine concentration being applicable to non-polar solvent prepared by the corresponding embodiment 1 of Fig. 5.Dichloromethane solution maximum absorption wavelength in Isopropylamine concentration increase process of this polymkeric substance does not almost change and maintains about 590nm, its absorbancy then increases along with Isopropylamine concentration the trend that aggregate performance goes out to reduce, therefore is become colorless from solution viewed from naked eyes by blueness.
The thermogravimetric curve being applicable to the poly ion liquid type basic indicator of non-polar solvent prepared by the corresponding embodiment 1 of Fig. 6.Curve weightlessness below 220 DEG C is less than 10, illustrates that this polymkeric substance has good thermostability.
The molecule measuring test result that the poly ion liquid type basic indicator being applicable to non-polar solvent prepared of the corresponding embodiment 1 of Fig. 7, example 2, example 3 records through gel permeation chromatography and corresponding n value.
Claims (10)
1. be applicable to a poly ion liquid type basic indicator for non-polar solvent, it is characterized in that, its structural formula is as follows:
Wherein, n is 10-50.
2. the preparation method being applicable to the poly ion liquid type basic indicator of non-polar solvent according to claim 1, is characterized in that, comprise the following steps:
Step a: reaction vessel is dewatered deoxygenation process;
Step b: add Tetra hydro Phthalic anhydride and DMF under nitrogen protection in reaction vessel, stirs the DMF solution obtaining Tetra hydro Phthalic anhydride;
Step c: add ethylene glycol under nitrogen protection in the DMF solution of the Tetra hydro Phthalic anhydride in step b, stirs;
Steps d: epoxy chloropropane is joined in the solution that step c obtains, under agitation react;
Step e: remaining epoxy chloropropane in the mixture be obtained by reacting in removing step d, adds N-Methylimidazole, under agitation react;
Step f: the mixture be obtained by reacting in step e is added in acetone, stir, solid-liquid separation is precipitated;
Step g: by the resolution of precipitate that obtains in step f in deionized water, be added drop-wise in the Methylene blue aqueous solution, under agitation react, solid-liquid separation is precipitated;
Step h: the precipitate with deionized water obtained in step g repeatedly rinsed, vacuum-drying, joins in methylene dichloride, stirs and forms mixture.
Step I: filtered by the mixture obtained in step h, obtain filtrate, rotary evaporation removing dichloromethane solvent, vacuum-drying, obtains the poly ion liquid type basic indicator being applicable to non-polar solvent.
3. be applicable to the preparation method of the poly ion liquid type basic indicator of non-polar solvent as claimed in claim 2, it is characterized in that, in described step c, the molecular fraction that described ethylene glycol accounts for Tetra hydro Phthalic anhydride is 1%-2%.
4. be applicable to the preparation method of the poly ion liquid type basic indicator of non-polar solvent as claimed in claim 2, it is characterized in that, in described steps d, described epoxy chloropropane and the mol ratio of Tetra hydro Phthalic anhydride are 1-1.3: 1.
5. be applicable to the preparation method of the poly ion liquid type basic indicator of non-polar solvent as claimed in claim 2, it is characterized in that, in described steps d, react under described stirring, its temperature is 95-120 DEG C, and its reaction times is 10-12 hour.
6. be applicable to the preparation method of the poly ion liquid type basic indicator of non-polar solvent as claimed in claim 2, it is characterized in that, the mol ratio of the Tetra hydro Phthalic anhydride in the DMF solution of the Tetra hydro Phthalic anhydride in the N-Methylimidazole added in described step e and step b is 1.1-1.5: 1.
7. be applicable to the preparation method of the poly ion liquid type basic indicator of non-polar solvent as claimed in claim 2, it is characterized in that, in described step e, react under described stirring, its temperature of reaction is 80-95 DEG C, and its reaction times is 4-6 days.
8. be applicable to the preparation method of the poly ion liquid type basic indicator of non-polar solvent as claimed in claim 2, it is characterized in that, in described step f, the volume ratio of the mixture obtained in described acetone and step e is 9-13: 1.
9. be applicable to the preparation method of the poly ion liquid type basic indicator of non-polar solvent as claimed in claim 2, it is characterized in that, in described step g, in described tropeolin-D and step f gained precipitate in the mol ratio of TMSIM N imidazole group be 1.2-1.8: 1.
10. be applicable to the preparation method of the poly ion liquid type basic indicator of non-polar solvent as claimed in claim 2, it is characterized in that, in described step g, react under described stirring, its temperature of reaction is 5-25 DEG C, and its reaction times is 10-20 hour.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108676173A (en) * | 2018-05-18 | 2018-10-19 | 东华大学 | Using ionic bond as poly ion liquid of skeleton and preparation method thereof |
| CN114018906A (en) * | 2021-09-28 | 2022-02-08 | 神美科技有限公司 | Test paper for detecting nitrite content and preparation method thereof |
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| CN102199280A (en) * | 2011-04-08 | 2011-09-28 | 浙江大学 | Fluoro-polyester resin and preparation method and application thereof |
| CN104151535A (en) * | 2014-08-09 | 2014-11-19 | 河北工业大学 | Segmented polyester copolymer and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102199280A (en) * | 2011-04-08 | 2011-09-28 | 浙江大学 | Fluoro-polyester resin and preparation method and application thereof |
| CN104151535A (en) * | 2014-08-09 | 2014-11-19 | 河北工业大学 | Segmented polyester copolymer and preparation method thereof |
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| GAOSHAN SI ET.AL: "Novel chromium complexes with a [OSSO]-type bis(phenolato) dianionic ligand mediate the alternating ring-opening copolymerization of epoxides and phthalic anhydride", 《POLYMER CHEMISTRY》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108676173A (en) * | 2018-05-18 | 2018-10-19 | 东华大学 | Using ionic bond as poly ion liquid of skeleton and preparation method thereof |
| CN108676173B (en) * | 2018-05-18 | 2020-12-18 | 东华大学 | Polyion liquid with ionic bond as framework and preparation method thereof |
| CN114018906A (en) * | 2021-09-28 | 2022-02-08 | 神美科技有限公司 | Test paper for detecting nitrite content and preparation method thereof |
| CN114018906B (en) * | 2021-09-28 | 2024-03-12 | 神美科技有限公司 | Test paper for detecting nitrite content and preparation method thereof |
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