CN108070049A - A kind of preparation method of quaternary ammonium salt ionic liquid polymer - Google Patents

A kind of preparation method of quaternary ammonium salt ionic liquid polymer Download PDF

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Publication number
CN108070049A
CN108070049A CN201611003885.6A CN201611003885A CN108070049A CN 108070049 A CN108070049 A CN 108070049A CN 201611003885 A CN201611003885 A CN 201611003885A CN 108070049 A CN108070049 A CN 108070049A
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China
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liquid polymer
vinyl
quaternary ammonium
ammonium salt
ionic liquid
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CN201611003885.6A
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Chinese (zh)
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丁云杰
王涛
吕元
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中国科学院大连化学物理研究所
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Publication of CN108070049A publication Critical patent/CN108070049A/en

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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F212/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F212/02Monomers containing only one unsaturated aliphatic radical
    • C08F212/04Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F212/14Monomers containing only one unsaturated aliphatic radical containing one ring substituted by heteroatoms or groups containing heteroatoms
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F212/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F212/34Monomers containing two or more unsaturated aliphatic radicals
    • C08F212/36Divinylbenzene
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F214/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
    • C08F214/02Monomers containing chlorine
    • C08F214/14Monomers containing three or more carbon atoms
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G
    • C08J9/00Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G
    • C08J2325/00Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Derivatives of such polymers
    • C08J2325/18Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G
    • C08J2327/00Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers
    • C08J2327/02Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment
    • C08J2327/04Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms

Abstract

The invention discloses a kind of preparation methods of quaternary ammonium salt ionic liquid polymer, belong to materials synthesis and application field.The ion liquid polymer is polymerized by the chloromethyl compound containing vinyl, containing the compound of N element and other comonomers.Such ion liquid polymerization material has excellent thermal stability and chemical stability.Preparation method provided by the invention, simple for process, porous polymer aperture obtained and specific surface area are adjustable, of low cost, can be used as catalyst, catalyst carrier, seperation film, battery material, gas storage material etc..

Description

A kind of preparation method of quaternary ammonium salt ionic liquid polymer

Technical field

The invention belongs to polymer material fields, are related to a kind of preparation method of new quaternary ammonium salt ionic liquid polymer.

Background technology

In recent decades, porous organic polymer is in many necks such as catalysis, gas storage, biomedical and battery new materials Domain has been widely available application.Synthesizing new functional form organic polymer is paid high attention to be subject to researcher.Wherein, organic polymer The synthetic method of object there has been more standardization in today and explore, meanwhile, porous organic polymer is also to connect organic, metal Bridge between organic and macromolecular chemistry.

Ionic liquid is widely used as environmentally friendly solvent because of its unique physical and chemical performance, meanwhile, may be used also To promote the process of a variety of chemical reactions.However, expensive ionic liquid is unable to large-scale production, the synthesis of ionic liquid can produce Raw a variety of toxic wastes, while the separation of ionic liquid and product etc. is consumed energy high and is easily lost.These shortcomings all limit The development of ionic liquid.And a kind of effective ways for solving these problems are by supported ionic liquids.Ionic liquid is consolidated at present There are mainly two types of methods for loadization:One kind be by ionic liquid absorption on a solid carrier, and it is another it is more commonly used be to utilize Covalently bound mode by ionic liquid supported on a solid carrier.For example, Dae Yoon Chi et al. (Angew.Chem.2004,116,489;Adv.Synth.Catal.2006,348,1719) it is by using polystyrene resin Carrier, it is with the crosslinking agent of different carbon chain lengths that imidazole salts are immobilized on polymer, it is applied and is taken in nucleophilic fluorination reaction Obtained good catalytic activity and stability.

Although seeing that the research of ion liquid polymer is increasingly goed deep at present, current synthesis technology is complicated, and ionic liquid The stability of polymer also has much room for improvement, so the application of ion liquid polymer faces huge challenge.

The content of the invention

Disadvantages described above and improvement for the prior art need, and the present invention provides new quaternary ammonium salt ionic liquid polymer Preparation method, its object is to methods easy to use first to synthesize ion liquid polymer, by optimum synthesis raw material and Technique solves current ion liquid polymer production cost height, the problem of synthesis technology complexity.

It realizes there are two types of technical schemes:Because the material obtained by vinyl polymerization proves have by extensive There are very high thermal stability and chemical stability.Scheme one be by vinylated quaternary ammonium salt and other vinyl comonomers into Row polymerization obtains quaternary ammonium salt ionic liquid compound;Scheme second is that obtain the polymer containing halogen methyl by vinyl polymerization, Then it is crosslinked to obtain quaternary ammonium salt ionic liquid polymer with imidazoles, tertiary amine.

To achieve the above object, a kind of preparation method of the quaternary ammonium salt ionic liquid polymer provided according to the present invention, institute Stating quaternary ammonium salt ionic liquid polymer can prepare as follows.

At 20-100 DEG C of temperature, inert atmosphere, by the halomethyl compounds containing vinyl and the chemical combination containing N element Object is dissolved in organic solvent, and 1-48h is heated at 20-100 DEG C, then adds in vinyl comonomer and radical initiator, 20- 1-48h is reacted at 100 DEG C.After material takes out, washed using methanol, be dried in vacuo 1-48h at 20-100 DEG C, obtain ionic liquid Polymer.

It can be methanol, ethyl alcohol, dichloromethane, chloroform, tetrahydrofuran, benzene, toluene, N, N- bis- to polymerize solvent for use One or more in the protics such as methylformamide, N, N- dimethyl sulfoxide (DMSO)s or non-protonic solvent.It is described to contain vinyl Halomethyl compounds for p-chloromethyl styrene, allyl chloride, in bromometllylstyrene, allyl bromide, bromoallylene, allyl iodide It is one or more.The compound containing N element is imidazoles, benzimidazole, pyridine, bipyridyl, trimethylamine, triethylamine, three One or more in ethanolamine, tri-n-butylamine, triamylamine, trihexylamine, three heptyl amices, trioctylamine.The comonomer be styrene, One or more in the vinyl compounds such as divinylbenzene, vinylpyridine, vinyl naphthalene.The radical initiator is Cyclohexanone peroxide, dibenzoyl peroxide, tert-butyl hydroperoxide, one kind of azodiisobutyronitrile or azobisisoheptonitrile or It is a variety of.The molar ratio of halomethyl compounds and comonomer containing vinyl is 0.01-100, is preferably 0.1-10.Contain second The molar ratio of the halomethyl compounds of alkenyl and the compound containing N element is 0.01-100.Halomethylation containing vinyl The molar ratio for closing object and radical initiator is 0.01-100.

A kind of preparation method of the quaternary ammonium salt ionic liquid polymer provided according to the present invention, the quaternary ammonium salt ionic liquid Polymer can also be prepared as follows.

At 20-100 DEG C of temperature, inert atmosphere, by halomethyl compounds and vinyl comonomer containing vinyl React 1-48h.After material takes out, 1-48h is dried in vacuo at 20-100 DEG C.Resulting polymers are dissolved in containing N element chemical combination In the organic solvent of object, 1-48h is reacted at 20-100 DEG C.After material takes out, washed using methanol, be dried in vacuo at 20-100 DEG C 1-48h obtains ion liquid polymer.

It can be methanol, ethyl alcohol, dichloromethane, chloroform, tetrahydrofuran, benzene, toluene, N, N- bis- to polymerize solvent for use One or more in the protics such as methylformamide, N, N- dimethyl sulfoxide (DMSO)s or non-protonic solvent.It is described to contain vinyl Halomethyl compounds for p-chloromethyl styrene, allyl chloride, in bromometllylstyrene, allyl bromide, bromoallylene, allyl iodide It is one or more.The compound containing N element is imidazoles, benzimidazole, pyridine, bipyridyl, trimethylamine, triethylamine, three One or more in ethanolamine, tri-n-butylamine, triamylamine, trihexylamine, three heptyl amices, trioctylamine.The comonomer be styrene, One or more in the vinyl compounds such as divinylbenzene, vinylpyridine, vinyl naphthalene.The radical initiator is Cyclohexanone peroxide, dibenzoyl peroxide, tert-butyl hydroperoxide, one kind of azodiisobutyronitrile or azobisisoheptonitrile or It is a variety of.The molar ratio of halomethyl compounds and comonomer containing vinyl is 0.1-20, is preferably 0.1-10.Contain ethylene The molar ratio of the halomethyl compounds of base and the compound containing N element is 0.1-20.Halomethyl compounds containing vinyl Molar ratio with radical initiator is 0.01-10.

Since quaternary ammonium salt ion is embedded in polymer backbone, the chemical stability and thermal stability of polymer are added, together When also promote the dispersion degree of quaternary ammonium salt ion, be conducive to quaternary ammonium salt ionic liquid polymer catalyst, catalyst carrier, The application in the fields such as seperation film, gas storage material.

In the preparation process in accordance with the present invention, the molar ratio of the halomethyl compounds containing vinyl and comonomer can be adjusted Save the pore structure of porous polymer material;Change polymerization solvent for use, the pore size of porous polymer material can be adjusted.Change Become the species of the compound containing N element, different quaternary amine ion liquid polymers can be made.

The advantage of the invention is that:

(1) poromeric preparation method provided by the invention is Raolical polymerizable, and synthetic method is simple, generation Porous material room temperature under insoluble in the common organic solvent such as arene, alcohols, dichloromethane, tetrahydrofuran in addition Apparent Swelling will not wherein occur, there is higher chemical stability.

(2) quaternary ammonium salt ionic liquid polymer provided by the invention in pore passage structure and skeleton quaternary ammonium salt contain measurer There is controllability.The pore size of polymer can be regulated and controled, specific surface area, using as different purposes.

Description of the drawings

Fig. 1 is the ion liquid polymer in embodiment 113C solid state nmrs spectrogram (13C CP-MAS NMR)。

Fig. 2 is nitrogen adsorption-desorption isotherm of the ion liquid polymer in embodiment 1.

Fig. 3 is the ion liquid polymer in embodiment 213C solid state nmrs spectrogram (13C CP-MAS NMR)。

Fig. 4 is nitrogen adsorption-desorption isotherm of the ion liquid polymer in embodiment 2.

Fig. 5 is the ion liquid polymer in embodiment 313C solid state nmrs spectrogram (13C CP-MAS NMR)。

Fig. 6 is nitrogen adsorption-desorption isotherm of the ion liquid polymer in embodiment 3.

Fig. 7 is the ion liquid polymer in embodiment 413C solid state nmrs spectrogram (13C CP-MAS NMR)。

Fig. 8 is nitrogen adsorption-desorption isotherm of the ion liquid polymer in embodiment 4.

Fig. 9 is the ion liquid polymer in embodiment 513C solid state nmrs spectrogram (13C CP-MAS NMR)。

Figure 10 is nitrogen adsorption-desorption isotherm of the ion liquid polymer in embodiment 5.

Figure 11 is the ion liquid polymer in embodiment 613C solid state nmrs spectrogram (13C CP-MAS NMR)。

Figure 12 is nitrogen adsorption-desorption isotherm of the ion liquid polymer in embodiment 6.

Specific embodiment

Following embodiments carry out deeper into explanation the present invention, but do not limit invention which is intended to be protected.

Embodiment 1

Under 25 DEG C and inert gas shielding atmosphere, 1.5g is sequentially added into the kettle with polytetrafluoro liner to chloromethyl Styrene, 0.32g imidazoles and 30mL N in N '-dimethyl formamide solvent (DMF), are stirred for 24 hours at 100 DEG C, added in afterwards 1.5g divinylbenzene monomers after stirring evenly, are slowly added to 0.075g radical initiator azodiisobutyronitriles, stir 0.5h Afterwards, solvent thermal polymerization is for 24 hours at 100 DEG C.After reaction, washed with methanol, reaction product is dried in vacuo at 65 DEG C 10h is denoted as PSIS-1 to get ion liquid polymer.

Embodiment 2

Under 25 DEG C and inert gas shielding atmosphere, 1.5g is sequentially added into the kettle with polytetrafluoro liner to chloromethyl Styrene, 1.5g divinylbenzene monomers and 30mL N, after N '-dimethyl formamide solvent stirs evenly, are slowly added to 0.075g radical initiator azodiisobutyronitriles, after stirring 0.5h, solvent thermal polymerization is for 24 hours at 100 DEG C.After reaction, Reaction product is dried in vacuo 10h at 65 DEG C, obtains polymer.2.0g polymer is taken to be dissolved in containing the organic of 0.21g imidazoles In solution, stirred for 24 hours at 100 DEG C.It is washed with methanol, reaction product is dried in vacuo 10h at 65 DEG C, ionic liquid is obtained and gathers Object is closed, is denoted as PSIS-2.

Embodiment 3

In embodiment 3, in addition to 0.32g imidazoles is changed to 0.28g trimethylamines, remaining operation is same as Example 1, obtains To ion liquid polymer, PSIS-3 is denoted as.

Embodiment 4

In example 4, in addition to 0.32g imidazoles is changed to 0.48g triethylamines, remaining operation is same as Example 1, obtains To ion liquid polymer, PSIS-4 is denoted as.

Embodiment 5

In embodiment 5, in addition to 0.32g imidazoles is changed to 0.70g triethanolamines, remaining operation is same as Example 1, Ion liquid polymer is obtained, is denoted as PSIS-5.

Embodiment 6

In embodiment 6, in addition to 1.5g p-chloromethyl styrenes are changed to 0.69g chloropropenes, remaining operation and implementation Example 1 is identical, obtains ion liquid polymer, is denoted as PSIS-6.

Embodiment 7

In embodiment 6, in addition to 1.5g p-chloromethyl styrenes are changed to 1.45g p-chlorostyrenes, remaining operation with Embodiment 1 is identical, and reaction at this time cannot obtain polymer.Illustrate when the halomethyl compounds illustrated without using the present invention, no Quaternary ammonium salt ionic liquid polymer can be formed.

Claims (6)

1. a kind of preparation method of quaternary ammonium salt ionic liquid polymer, it is characterised in that:The ion liquid polymer is by containing The halomethyl compounds of vinyl trigger polymerization containing the compound of N element and other comonomers via radical initiator It forms;
The halomethyl compounds containing vinyl are p-chloromethyl styrene, allyl chloride, to bromometllylstyrene, allyl One or two or more kinds in bromide, allyl iodide;
The compound containing N element for imidazoles, benzimidazole, pyridine, bipyridyl, trimethylamine, triethylamine, triethanolamine, One or two or more kinds in tri-n-butylamine, triamylamine, trihexylamine, three heptyl amices, trioctylamine
The comonomer is one kind in the vinyl compounds such as styrene, divinylbenzene, vinylpyridine, vinyl naphthalene Or two kinds or more;
The molar ratio range of the halomethyl compounds of vinyl and the compound amount containing N element is 0.1-20, is preferably 1; The halomethyl compounds of vinyl are 0.1-20 with the molar ratio range of comonomer dosage, are preferably 1.
2. the preparation method of quaternary ammonium salt ionic liquid polymer according to claim 1, it is characterised in that:The free radical draws Hair agent is cyclohexanone peroxide, dibenzoyl peroxide, tert-butyl hydroperoxide, azodiisobutyronitrile or azobisisoheptonitrile One or two or more kinds, the halomethyl compounds of vinyl are 0.01-10 with the molar ratio range of radical initiator dosage.
3. the preparation method of quaternary ammonium salt ionic liquid polymer according to claim 1, it is characterised in that:It is divided into two kinds:
A kind of is first by the halomethyl compounds of vinyl with being stirred at the compound containing N element in organic solvent 20-100 DEG C 1-48h is mixed, adds at 20-100 DEG C of comonomer and radical initiator and reacts 1-48h;Material uses organic solvent after taking out It washs, 1-48h is dried at 20-100 DEG C and obtains ion liquid polymer;
Or, another kind is that first the halomethyl compounds of vinyl and comonomer exist in organic solvent through radical initiator 1-48h is reacted at 20-100 DEG C, drying 1-48h obtains polymer at 20-100 DEG C after material taking-up, dissolves a polymer in organic In solvent, add at 20-100 DEG C of the compound containing N element and stir 1-48h, after material takes out, using organic solvent washing, After at 20-100 DEG C dry 1-48h obtain ion liquid polymer.
4. the preparation method of quaternary ammonium salt ionic liquid polymer according to claim 3, organic solvent used in polymerization can be with For methanol, ethyl alcohol, dichloromethane, chloroform, tetrahydrofuran, benzene, toluene, N,N-dimethylformamide, N, N- dimethyl Asia One or two or more kinds in the protics such as sulfone or non-protonic solvent.
5. a kind of quaternary ammonium salt ionic liquid polymer that any the methods of claim 1-4 prepare.
6. the application of quaternary ammonium salt ionic liquid polymer, can be directly used for CO described in a kind of claim 52Cycloaddition reaction is urged Agent and catalyst carrier, solvent resistant nanofiltration separation membrane or CO2And H2Gas storage material.
CN201611003885.6A 2016-11-15 2016-11-15 A kind of preparation method of quaternary ammonium salt ionic liquid polymer CN108070049A (en)

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Application publication date: 20180525