CN108409964A - Using ionic liquid as poly ion liquid of skeleton and preparation method thereof - Google Patents
Using ionic liquid as poly ion liquid of skeleton and preparation method thereof Download PDFInfo
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- CN108409964A CN108409964A CN201810485172.0A CN201810485172A CN108409964A CN 108409964 A CN108409964 A CN 108409964A CN 201810485172 A CN201810485172 A CN 201810485172A CN 108409964 A CN108409964 A CN 108409964A
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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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0605—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0616—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only two nitrogen atoms in the ring
Abstract
The present invention provides a kind of using ionic liquid as poly ion liquid of skeleton and preparation method thereof.It is described using ionic liquid as the poly ion liquid of skeleton, which is characterized in that its structural formula is：Wherein, n is 10 15.It is above-mentioned using ionic liquid as the preparation method of the poly ion liquid of skeleton, which is characterized in that including：Using imidazoles and epoxychloropropane as raw material, poly (ECH MIM) is synthesized by opening；Then the aqueous solution of poly (ECH MIM) is mixed with the aqueous solution of neopelex, generates precipitation；It is precipitated finally by standing separation, drying sediment obtains the poly ion liquid using ionic liquid as skeleton.In view of in traditional poly ion liquid, ion is mainly hung in high polymer long chain in the form of a functional group, the high polymer with ion pair branch can be considered as, and what ion itself was combined with main chain, it is rarely reported by the poly ion liquid of skeleton of ionic liquid, which possesses certain researching value.
Description
Technical field
The present invention relates to a kind of novel poly ion liquids, specifically, referring to a kind of using ionic liquid as skeleton
The preparation method of novel poly ion liquid.
Background technology
Ionic liquid is that one kind is in a liquid state at normal temperatures, the salt being made of zwitterion.Ionic liquid is as a kind of liquid
Organic salt shows unique physicochemical properties：Vapour pressure is almost nil under room temperature；To organic and inorganic, organic metal substance
There is highly dissoluble；Thermal stability is high；The advantages that ionic conductivity is good.Ionic liquid is urged in green solvent, fine chemistry industry
The application aspects such as reaction, substance separation side, electricity analysis and emerging nanometer biotechnology cause the extensive concern of people.Polyion
Liquid is referred to as ion macromolecule, is a kind of interior macromolecule for including ionic liquid zwitterion pair of repetitive unit.Gather from
Ion in sub- liquid is fixed on segment, but still can maintain the property of itself, combines macromolecule and ionic liquid
The characteristic of both bodies.Poly ion liquid has extremely strong designability, other than the structure of zwitterion and type, macromolecule
The density of position and ion of the structure of chain with composition, ion pair on strand can be controlled.By to gather from
The structure of sub- liquid is designed, and can obtain large quantities of new function poly ion liquids, can apply to dispersant, phase turns
Move agent, adsorbent, release agent, ion conductive material, nanocomposite, bio-medical material etc..
In current poly ion liquid, ion is mainly hung in high polymer long chain in the form of a functional group, can be regarded
For the high polymer with ion pair branch, and what ion itself was combined with main chain, using ionic liquid as the poly ion liquid of skeleton
It is rarely reported.With deep and application technology the development of poly ion liquid theoretical research, the structure to poly ion liquid is needed
Fine design is carried out according to demand with performance, synthesizes the new type functional poly ion liquid material more haveing excellent performance.Design is closed
It to abundant poly ion liquid type, research structure property relationship and is opened by the poly ion liquid of skeleton of ionic liquid at novel
The application of function of Fa Qixin has positive effect.
It is found by being retrieved to existing literature, poly ion liquid is mainly polymerize by conventional free radical, and living radical is poly-
It closes, prepared by the methods of cationic polymerization.Green et al. exists《Macromolecular chemistry and physics》2011
2522-2528 pages of volume 212 of year has delivered " Alkyl-substituted N-Vinylimidazolium polymerized
ionic liquids：Thermal properties and ionic conductivities ", this article author is by ionic liquid
Monomer directly carries out free radical polymerization, has synthesized a series of imidazoles poly ion liquids with different length alkyl substituent.
Texer et al. exists《Macromolecular Rapid Communications》2012 69-74 pages of volume 33 deliver
“Triblock Copolymer Based on Poly(propylene oxide)and Poly(1-[11-
Acryloylundecyl] -3-methyl-imidazolium bromide) ", this article author uses a kind of macromole evocating agent
PPO-diOH makes ionic liquid monomer at 60 c using hexamethyl trien-bromination copper complex as catalyst
Atom transfer radical polymerization (ATRP) occurs, has synthesized the poly ion liquid for being named as Poly (ILBr-b-PO-b-ILBr).
Zhang et al. exists《Polymer Chemistry》2016 5099-5112 pages of volume 7 delivered " Cationic
polymerization ofp-methylstyrene in selected ionic liquids and polymerization
Mechanism ", this article author carry out isobutylvinyl ether under 0 degree Celsius in a kind of ionic liquid [OMIM] [BF4]
Cationic polymerization has synthesized a series of poly ion liquids using a variety of aided initiatings.Using different polymerizations, can make
The different poly ion liquid of standby structure.However, in current poly ion liquid, ion is mainly hung in the form of a functional group
In in high polymer long chain, being considered as the high polymer with ion pair branch, and what ion itself was combined with main chain, with ionic liquid
Body is that the poly ion liquid of skeleton is rarely reported.
Invention content
The purpose of the present invention is to provide a kind of using ionic liquid as poly ion liquid of skeleton and preparation method thereof.
In order to achieve the above object, the present invention provides a kind of using ionic liquid as the poly ion liquid of skeleton, feature
It is, structural formula is：
Wherein, n 10-15.
The present invention also provides above-mentioned using ionic liquid as the preparation method of the poly ion liquid of skeleton, and feature exists
In, including：Using imidazoles and epoxychloropropane as raw material, poly (ECH-MIM) is synthesized (such as formula (1) institute by opening
Show)；Then the aqueous solution of poly (ECH-MIM) is mixed with the aqueous solution of neopelex (shown in formula (2)), is generated
Precipitation；It is precipitated finally by standing separation, drying sediment obtains using ionic liquid being the poly ion liquid of skeleton (such as formula (3)
It is shown).
The present invention also provides above-mentioned using ionic liquid as the preparation method of the poly ion liquid of skeleton, and feature exists
In, including：
Step a：Water removal deoxygenation processing is carried out to reaction vessel；
Step b：Ethyl alcohol, imidazoles and epoxychloropropane is added into reaction vessel under nitrogen protection, heating stirring is anti-
It answers, obtains poly (ECH-MIM)；
Step c：After the poly (ECH-MIM) that step b is obtained is cooled to room temperature, is dried in baking oven, obtain poly
(ECH-MIM)；
Step d：The poly (ECH-MIM) that step c is obtained is soluble in water, mixed with sodium dodecyl benzene sulfonate aqueous solution
It closes, generates precipitation；
Step e：The precipitation standing separation that step d is obtained, is dried to obtain the poly ion liquid using ionic liquid as skeleton.
Preferably, the molar ratio of imidazoles and epoxychloropropane is 1: 0.9-1.1 in the step b.
Preferably, the reaction temperature in the step b is 70-80 degrees Celsius, and the reaction time is 6-8 days.
Preferably, the drying temperature in the step c is 80-90 degrees Celsius, time 10-12 hour.
Preferably, in the step d, the molar ratio of poly (ECH-MIM) and neopelex is 1: 1.8-
2.2。
Preferably, in the step d poly (ECH-MIM) aqueous solution a concentration of 0.5-1mol/L, detergent alkylate
Sodium sulfonate concentration of aqueous solution is identical as the former.
Preferably, time of repose is 10-12 hours in the step e, and drying temperature is 80-90 degrees Celsius, time 10-
12 hours.
The principle of the present invention is, using ethyl alcohol as solvent, using imidazoles and epoxychloropropane as raw material, passes through opening
Synthesize poly (ECH-MIM).Then the aqueous solution of the aqueous solution of poly (ECH-MIM) and shown neopelex is mixed
It closes, by ion-exchange reactions, dodecyl benzene sulfonic acid anion is made to replace chlorion, generated using ionic liquid as the new of skeleton
The precipitation of type poly ion liquid.It is precipitated finally by standing separation, drying sediment obtains pure using ionic liquid as bone
The novel poly ion liquid of frame.Gained can be total to by the structure of the novel poly ion liquid of skeleton of ionic liquid by nuclear-magnetism
The hydrogen that shakes spectrum detection, infrared spectrum, gel permeation chromatography, differential scanning calorimetry, thermal weight loss etc. are used as assistant analysis means.
Compared with prior art, the beneficial effects of the invention are as follows：
It is prepared in accordance with the present invention using ionic liquid as the novel poly ion liquid of skeleton, in structure with traditional polyion
There are larger differences for liquid.In current poly ion liquid, ion is mainly hung in high polymer long chain in the form of a functional group,
Can be considered as the high polymer with ion pair branch, and what ion itself was combined with main chain, using ionic liquid as skeleton gather from
Sub- liquid is rarely reported.The present invention prepare using ionic liquid as the poly ion liquid of skeleton to abundant poly ion liquid type,
It research structure property relationship and develops its new application of function and has positive effect.
Description of the drawings
Fig. 1 be the present invention prepare using ionic liquid as the nuclear magnetic spectrogram of the novel poly ion liquid of skeleton；
Wherein, Fig. 1 a, b, c distinguish prepared by corresponding embodiment 1, example 2, example 3 using ionic liquid as skeleton it is novel gather from
The one-dimensional nucleus magnetic hydrogen spectrum figure of sub- liquid.
Fig. 2 be the present invention prepare using ionic liquid as Fourier's infrared spectrum of the novel poly ion liquid of skeleton.
Fig. 3 be the present invention prepare using ionic liquid as the differential scanning calorimetry spectrogram of the novel poly ion liquid of skeleton.
Fig. 4 be the present invention prepare using ionic liquid as the thermogravimetric curve of the novel poly ion liquid of skeleton.
Prepared by Fig. 5 corresponding embodiments 1, example 2, example 3 oozes by the novel poly ion liquid of skeleton of ionic liquid through gel
Saturating chromatographic molecular weight and its corresponding n values test result.
Specific implementation mode
Present invention will be further explained below with reference to specific examples.It should be understood that these embodiments are merely to illustrate the present invention
Rather than it limits the scope of the invention.In addition, it should also be understood that, after reading the content taught by the present invention, people in the art
Member can make various changes or modifications the present invention, and such equivalent forms equally fall within the application the appended claims and limited
Range.
Embodiment 1
It is a kind of using ionic liquid as the poly ion liquid of skeleton, shown in structural formula such as formula (3), n therein such as Fig. 5 institutes
Show.Described is by the preparation method of the poly ion liquid of skeleton of ionic liquid：
Step a：Water removal deoxygenation processing is carried out to 1000 milliliters of three-neck flasks, water removal deoxygenation processing is：It will be clean
1000 milliliters of three-neck flasks fully dried under 90 degrees Celsius 3 hours, taking-up is cooled to room temperature, and is passed through nitrogen；
Step b：Under nitrogen protection, 500mL ethyl alcohol, 540g imidazoles and 400g epoxychloropropane are added into flask,
After so that raw material is completely dissolved, in the case where 80 degrees Celsius of oil baths heat, persistently it is stirred to react 7 days, obtains poly (ECH-MIM)；
Step c：After the poly (ECH-MIM) that step b is obtained is cooled to room temperature (25 DEG C), it is transferred in culture dish.It will
Raw material is placed in vacuum drying oven and dries 12 hours for 90 degrees Celsius, obtains pure poly (ECH-MIM)；
Step d：The poly (ECH-MIM) that step c is obtained is dissolved in deionized water, the aqueous solution 50 of 0.8mol/L is configured
Milliliter, mixes with 100 milliliters of 0.8mol/L sodium dodecyl benzene sulfonate aqueous solutions, generates precipitation；
Step e：The mixture that step d is obtained stands 12 hours precipitation and separations, and 90 degrees Celsius are dried to obtain with ionic liquid
Body is the novel poly ion liquid of skeleton.
Embodiment 2
It is a kind of using ionic liquid as the poly ion liquid of skeleton, shown in structural formula such as formula (3), n therein such as Fig. 5 institutes
Show.Described is by the preparation method of the poly ion liquid of skeleton of ionic liquid：
Step a：Water removal deoxygenation processing is carried out to 500 milliliters of three-neck flasks, water removal deoxygenation processing is：By cleaning
500 milliliters of three-neck flasks are fully dried 3 hours under 90 degrees Celsius, and taking-up is cooled to room temperature, and is passed through nitrogen；
Step b：Under nitrogen protection, 200mL ethyl alcohol, 270g imidazoles and 200g epoxychloropropane are added into flask,
After so that raw material is completely dissolved, in the case where 80 degrees Celsius of oil baths heat, persistently it is stirred to react 7 days, obtains poly (ECH-MIM)；
Step c：After the poly (ECH-MIM) that step b is obtained is cooled to room temperature, it is transferred in culture dish.Raw material is set
It is dried 12 hours for 80 degrees Celsius in vacuum drying oven, obtains pure poly (ECH-MIM)；
Step d：The poly (ECH-MIM) that step c is obtained is dissolved in deionized water, the aqueous solution 20 of 0.8mol/L is configured
Milliliter, mixes with 40 milliliters of 0.8mol/L sodium dodecyl benzene sulfonate aqueous solutions, generates precipitation；
Step e：The mixture that step d is obtained stands 12 hours precipitation and separations, and 90 degrees Celsius are dried to obtain with ionic liquid
Body is the novel poly ion liquid of skeleton.
Embodiment 3
It is a kind of using ionic liquid as the poly ion liquid of skeleton, shown in structural formula such as formula (3), n therein such as Fig. 5 institutes
Show.Described is by the preparation method of the poly ion liquid of skeleton of ionic liquid：
Step a：Water removal deoxygenation processing is carried out to 250 milliliters of three-neck flasks, water removal deoxygenation processing is：By cleaning
250 milliliters of three-neck flasks are fully dried 3 hours under 90 degrees Celsius, and taking-up is cooled to room temperature, and is passed through nitrogen；
Step b：Under nitrogen protection, 100mL ethyl alcohol, 135g imidazoles and 100g epoxychloropropane are added into flask,
After so that raw material is completely dissolved, in the case where 80 degrees Celsius of oil baths heat, persistently it is stirred to react 7 days, obtains poly (ECH-MIM)；
Step c：After the poly (ECH-MIM) that step b is obtained is cooled to room temperature, it is transferred in culture dish.Raw material is set
It is dried 12 hours for 80 degrees Celsius in vacuum drying oven, obtains pure poly (ECH-MIM)；
Step d：The poly (ECH-MIM) that step c is obtained is dissolved in deionized water, the aqueous solution 10 of 0.8mol/L is configured
Milliliter, mixes with 20 milliliters of 0.8mol/L sodium dodecyl benzene sulfonate aqueous solutions, generates precipitation；
Step e：The mixture that step d is obtained stands 12 hours precipitation and separations, and 90 degrees Celsius are dried to obtain with ionic liquid
Body is the novel poly ion liquid of skeleton.
Sample result is shown in attached drawing
Fig. 1 a, 1b, 1c difference corresponding embodiment 1, example 2, example 3 prepare using ionic liquid as the novel polyion liquid of skeleton
The one-dimensional nucleus magnetic hydrogen spectrum figure of body.Peak wherein on imidazoles is in 7.0ppm and farther place；The hydrogen peak belonged on epoxychloropropane is located at
2-4ppm ranges；The peak of 7.0ppm or so belongs to benzene ring hydrogen；Peak between 1-2ppm belongs to dodecyl chain；2.5ppm
Peak belongs to hydroxyl, overlaps with solvent peak.
Fig. 2 corresponding embodiments 1 prepare using ionic liquid as Fourier's infrared spectrum of the novel poly ion liquid of skeleton.
Positioned at 1568cm-1、1443cm-1What is located is the vibration peak of imidazoles ring skeleton in poly ion liquid；Positioned at 3431cm-1Place is alcohol
The stretching vibration peak of hydroxyl O-H；Positioned at 3112cm-1What is located is the stretching vibration peak of C-H on imidazole ring；Positioned at 2836cm-1Place
The stretching vibration peak of C-H on imidazoles ring substituents；Positioned at 1170cm-1What is located is the in-plane bending vibration peak of c h bond on imidazole ring；
Positioned at 1104cm-1Place is alcoholic extract hydroxyl group C-O stretching vibration peaks.
Prepared by Fig. 3 corresponding embodiments 1 composes by the differential scanning calorimetry of the novel poly ion liquid of skeleton of ionic liquid
Figure.
Fig. 4 corresponding embodiments 1 prepare using ionic liquid as the thermogravimetric curve curve of the novel poly ion liquid of skeleton
It is less than 10 in 300 degrees Celsius or less weightless ratios, illustrates that the polymer has good thermal stability.
Prepared by Fig. 5 corresponding embodiments 1, example 2, example 3 oozes by the novel poly ion liquid of skeleton of ionic liquid through gel
A kind of molecular weight and its corresponding n values that saturating coefficients data measured by chromatography obtains, it was demonstrated that synthesis of novel poly ion liquid.
Claims (9)
1. a kind of using ionic liquid as the poly ion liquid of skeleton, which is characterized in that its structural formula is：
Wherein, n 10-15.
2. described in claim 1 using ionic liquid as the preparation method of the poly ion liquid of skeleton, which is characterized in that including：
Using imidazoles and epoxychloropropane as raw material, poly (ECH-MIM) is synthesized by opening；Then by poly (ECH-
MIM aqueous solution) is mixed with the aqueous solution of neopelex, generates precipitation；It precipitates, dries finally by standing separation
Sediment obtains the poly ion liquid using ionic liquid as skeleton.
3. described in claim 1 using ionic liquid as the preparation method of the poly ion liquid of skeleton, which is characterized in that including：
Step a：Water removal deoxygenation processing is carried out to reaction vessel；
Step b：Ethyl alcohol, imidazoles and epoxychloropropane is added into reaction vessel under nitrogen protection, heating is stirred to react, and is obtained
To poly (ECH-MIM)；
Step c：After the poly (ECH-MIM) that step b is obtained is cooled to room temperature, is dried in baking oven, obtain poly (ECH-
MIM)；
Step d：The poly (ECH-MIM) that step c is obtained is soluble in water, is mixed with sodium dodecyl benzene sulfonate aqueous solution, production
Raw precipitation；
Step e：The precipitation standing separation that step d is obtained, is dried to obtain the poly ion liquid using ionic liquid as skeleton.
4. as claimed in claim 3 using ionic liquid as the preparation method of the poly ion liquid of skeleton, which is characterized in that described
Step b in the molar ratio of imidazoles and epoxychloropropane be 1: 0.9-1.1.
5. as claimed in claim 3 using ionic liquid as the preparation method of the poly ion liquid of skeleton, which is characterized in that described
Step b in reaction temperature be 70-80 degrees Celsius, the reaction time be 6-8 days.
6. as claimed in claim 3 using ionic liquid as the preparation method of the poly ion liquid of skeleton, which is characterized in that described
Step c in drying temperature be 80-90 degrees Celsius, time 10-12 hour.
7. as claimed in claim 3 using ionic liquid as the preparation method of the poly ion liquid of skeleton, which is characterized in that described
Step d in, the molar ratio of poly (ECH-MIM) and neopelex is 1: 1.8-2.2.
8. as claimed in claim 3 using ionic liquid as the preparation method of the poly ion liquid of skeleton, which is characterized in that described
Step d in poly (ECH-MIM) aqueous solution a concentration of 0.5-1mol/L, sodium dodecyl benzene sulfonate aqueous solution concentration with before
Person is identical.
9. as claimed in claim 3 using ionic liquid as the preparation method of the poly ion liquid of skeleton, which is characterized in that described
Step e in time of repose be 10-12 hour, drying temperature be 80-90 degrees Celsius, time 10-12 hour.
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Cited By (1)
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