CN107200787A - A kind of imidazoles alginate ionic liquid and its synthetic method - Google Patents
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Abstract
The invention discloses a kind of imidazoles alginate ionic liquid and its synthetic method.The structure of the ionic liquid is as shown in shown below:Wherein R1、R3For H atom, alkyl (carbon chain lengths 1~20) or substituted hydrocarbon radical;R2For H atom or methyl;[Alg]‑For marine alga acid radical anion.The ionic liquid synthesized in the present invention is water-soluble and the state of clear is presented, and such ionic liquid can effectively play the characteristic of its marine alga acid radical anion, has important application in terms of material carrier, metal adsorption.Its synthetic method is mainly characterized by:Raw material is easily prepared, and cost is relatively low;The material of reaction condition and process green, nonpollution environment and harmful to human is produced;Synthetic method is simple, products pure no coupling product, and purification process is simple, is adapted to high-volume large-scale production.
Description
Technical field
The present invention relates to new material technology field, more particularly to a kind of imidazoles alginate ionic liquid and its synthesis
Method.
Background technology
Ionic liquid is with anion to be combined the low temperature or room temperature molten salt that are formed by the cation of different structure.Ion
Liquid possesses many excellent physicochemical properties, such as difficult volatilization, thermally-stabilised, wider electrochemical window and liquid phase are interval
Turn into the popular domain of research in recent years Deng so that ionic liquid, catalyzing and synthesizing, extract and separate, gas are absorbed, analysis is surveyed
There is important application in terms of examination, electrochemistry.Functionalized design is carried out to the zwitterion building stone of ionic liquid, can be with
Obtain the functionalized ion liquid for having the two characteristic concurrently.
Glyoxaline ion liquid is an important branch in ionic liquid, and this has benefited from low caused by glyoxaline cation
Fusing point, low viscosity, the advantage of high stability, field of ionic liquid was most for the report of this class ionic liquid in recent years, closed
It is theoretical gradually perfect into gradually ripe with research method.
Natural seaweed hydrochlorate is a kind of natural polymerses, in marine organisms marine alga, belongs to a kind of polysaccharide.
Sodium alginate is most common unitary alginate, can be dissolved in water, forms viscous aqueous solution, and heating can promote sodium alginate
Dissolving, obtains light yellow transparent solution.Sodium alginate has very strong sequestering, and stable complexing can be formed for metal ion
Thing.It therefore, it can as a kind of important metal absorbent.Sodium alginate contains more rich-COO—, with very high ion
Function of exchange, can be reacted with other materials, obtain different alginate derivatives.Sodium alginate can and Ca2+、
Co2+、Cu2+、Fe2+、Zn2+Deng divalent metal crosslinking, a kind of " egg-box " (egg-box) structure, this kind of alginic acid are formed
Salt is a kind of good hydrogel, with the function of keeping moisture, carry material.
The content of the invention
In order to solve the above technical problems, the present invention provides a kind of imidazoles alginate ionic liquid and its synthetic method.
The present invention's, including
A kind of imidazoles alginate ionic liquid, the structural formula of imidazoles alginate ion is as follows:
Wherein R1、R3For H atom, alkyl (carbon chain lengths 1~20) or substituted hydrocarbon radical;R2For H atom or methyl;[Alg]—
For marine alga acid radical anion.
Alkyl (carbon chain lengths 1~20) or substituted hydrocarbon radical can be methyl, ethyl, propyl group, butyl, amyl group, hexyl, pungent
Base, decyl, dodecyl, myristyl, cetyl, octadecyl, pi-allyl, acetonyl, cyanoethyl, ethyl acetate base,
Any one in acetenyl.
A kind of synthetic method of imidazoles alginate ionic liquid, comprises the following steps:According to imidazolium hydroxide:
Brand-new alginic acid=1:1~1.1 mol ratio mixes the two in a solvent, stirs, and centrifugation takes out clear after reaction terminates
Liquid, and remove solvent, you can obtain imidazoles alginate ionic liquid.
Above-mentioned use solvent can be the one or more such as water, dichloroethanes, isopropanol, preferably water or isopropanol.
Reaction temperature is room temperature to 75 DEG C, preferably room temperature;Reaction time is 1~72 hour.
The imidazoles alginate ionic liquid that the present invention is provided is specially:1,3- methylimidazole alginate ionic liquids
Body [C1Mim] [Alg], 1- methyl -3- ethyl imidazol(e) alginate ionic liquids [C2Mim] [Alg], 1- methyl -3- butyl imidazoles
Alginate ionic liquid [C4Mim] [Alg], 1- methyl -3- hexyl imidazolium alginate ionic liquids [C6mim][Alg]、1-
Methyl -3- octylimidazole alginate ionic liquids [C8Mim] [Alg], 1- methyl -3- decyl imidazoles alginate ionic liquids
[C10Mim] [Alg], 1- methyl -3- dodecyl imidazole alginate ionic liquids [C12Mim] [Alg], 1- methyl -3- 14
Alkyl imidazole alginate ionic liquid [C14Mim] [Alg], 1- methyl -3- cetyl imidazoles alginate ionic liquids
[C16Mim] [Alg], 1- methyl -3- octadecyl imidazoles alginate ionic liquids [C18Mim] [Alg], 1- methyl -3- allyls
Base imidazoles alginate ionic liquid [Amim] [Alg], 1- methyl -3- acetonyl imidazoles alginate ionic liquids
[MeCOCH2Mim] [Alg], 1- methyl -3- cyanoethyl imidazoles alginate ionic liquids [NCCH2Mim] [Alg], 1- methyl -3-
Ethyl acetate base imidazoles alginate ionic liquid [CH3CH2OOCCH2Mim] [Alg], 1- methyl -3- acetenyl imidazoles alginic acids
Ionic liquid [HCCH2Mim] [Alg], 1- ethyl -3- butyl imidazole alginate ionic liquids [C2C4Im] [Alg], 1- third
Base -3- butyl imidazole alginate ionic liquids [C3C4Im] [Alg], 1,3- dibutyl imidazoles alginate ionic liquids
[C4C4Im] [Alg], 1- butyl -3- amyl group imidazoles alginate ionic liquids [C4C5Im] [Alg], 1- butyl -3- hexyl imidazoliums
Alginate ionic liquid [C4C6Im] [Alg], 1,2,3- tri-methylimidazolium alginate ionic liquids [C1mmim][Alg]、1,
2- dimethyl -3- ethyl imidazol(e) alginate ionic liquids [C2Mmim] [Alg], 1,2- dimethyl -3- propyl imidazole alginic acids
Ionic liquid [C3Mmim] [Alg], 1,2- dimethyl -3- butyl imidazole alginate ionic liquids [C4mmim][Alg]。
The beneficial effects of the invention are as follows:
(1) marine alga acid ion is incorporated into ionic liquid so that product has the excellent of ionic liquid and alginate concurrently
Benign matter, with wide Research Prospects.
(2) imidazoles alginate ionic liquid belongs to the crossing domain of natural polymer and ionic liquid, is ionic liquid
The impressive progress of body industrial applications.
(3) this synthetic method raw material is easily prepared, and cost is relatively low;Reaction condition and process green, nonpollution environment and
The material of harmful to human is produced;Synthetic method is simple, products pure no coupling product, and purification process is simple, is adapted to high-volume scale
Production.
(4) imidazoles alginate ionic liquid has tempting application prospect, especially pharmaceutical carrier, water tariff collection,
The fields such as heavy metal ion adsorbed and functional polymer preparation have important application potentiality.
Embodiment
With reference to specific embodiment, the present invention is expanded on further.It should be understood that these embodiments are merely to illustrate the present invention
Rather than limitation the scope of the present invention.In addition, it is to be understood that after instruction content of the invention has been read, those skilled in the art
The present invention can be made various changes or modifications, these equivalent form of values equally fall within what the application appended claims were limited
Scope.
Example 1:1,3- methylimidazole alginate ionic liquids [C1mim][Alg].2.26g will be contained
The aqueous isopropanol of (0.020mol) 1,3- methylimidazole hydroxide and the brand-new containing 3.52g (0.020mol) alginic acid
The aqueous solution (solvent swelling state) is mixed, and after stirring 1 hour at room temperature, is carried out centrifugal treating to it and is taken out clear liquid, is removed after solvent
Obtain 1,3- methylimidazole alginate ionic liquids [C1Mim] [Alg], it is light yellow solid at room temperature.
Example 2:1- methyl -3- ethyl imidazol(e) alginate ionic liquids [C2mim][Alg].2.56g will be contained
The aqueous isopropanol of (0.020mol) 1- methyl -3- ethyl imidazol(e) hydroxide is with containing 3.52g (0.020mol) alginic acid
The brand-new aqueous solution (solvent swelling state) is mixed, and after stirring 1 hour at room temperature, is carried out centrifugal treating to it and is taken out clear liquid, is removed molten
1- methyl -3- ethyl imidazol(e) alginate ionic liquids [C is obtained after agent2Mim] [Alg], it is light yellow solid at room temperature.
Example 3:1- methyl -3- butyl imidazole alginate ionic liquids [C4mim][Alg].3.12g will be contained
The aqueous isopropanol of (0.020mol) 1- methyl -3- butyl imidazole hydroxide is with containing 3.52g (0.022mol) alginic acid
The brand-new aqueous solution (solvent swelling state) is mixed, and after stirring 2 hours at room temperature, is carried out centrifugal treating to it and is taken out clear liquid, is removed molten
1- methyl -3- butyl imidazole alginate ionic liquids [C is obtained after agent4Mim] [Alg], it is light yellow solid at room temperature.
Example 4:1- methyl -3- hexyl imidazolium alginate ionic liquids [C6mim][Alg].3.69g will be contained
The aqueous isopropanol of (0.020mol) 1- methyl -3- hexyl imidazolium hydroxide is with containing 3.52g (0.022mol) alginic acid
The brand-new aqueous solution (solvent swelling state) is mixed, and after stirring 4 hours at room temperature, is carried out centrifugal treating to it and is taken out clear liquid, is removed molten
1- methyl -3- hexyl imidazolium alginate ionic liquids [C is obtained after agent6Mim] [Alg], it is thick pale yellow at room temperature
Liquid.
Example 5:1- methyl -3- octylimidazole alginate ionic liquids [C8mim][Alg].4.25g will be contained
The aqueous isopropanol of (0.020mol) 1- methyl -3- octylimidazole hydroxide is with containing 3.52g (0.022mol) alginic acid
The brand-new aqueous solution (solvent swelling state) is mixed, and after stirring 8 hours at room temperature, is carried out centrifugal treating to it and is taken out clear liquid, is removed molten
1- methyl -3- octylimidazole alginate ionic liquids [C is obtained after agent8Mim] [Alg], it is thick pale yellow at room temperature
Liquid.
Example 6:1- methyl -3- decyl imidazoles alginate ionic liquids [C10mim][Alg].4.81g will be contained
The aqueous isopropanol of (0.020mol) 1- methyl -3- decyl imidazolium hydroxides is with containing 3.52g (0.020mol) alginic acid
The brand-new aqueous solution (solvent swelling state) is mixed, and after stirring 12 hours at room temperature, is carried out centrifugal treating to it and is taken out clear liquid, is removed molten
1- methyl -3- decyl imidazoles alginate ionic liquids [C is obtained after agent10Mim] [Alg], it is clear yellow viscous liquid at room temperature
Body.
Example 7:1- methyl -3- dodecyl imidazole alginate ionic liquids [C12mim][Alg].5.37g will be contained
The aqueous isopropanol of (0.020mol) 1- methyl -3- dodecyl imidazole hydroxide is with containing 3.87g (0.022mol) marine alga
The brand-new aqueous solution (solvent swelling state) mixing of acid, after stirring 24 hours at room temperature, carries out centrifugal treating to it and takes out clear liquid, remove
Go after solvent to obtain 1- methyl -3- dodecyl imidazole alginate ionic liquids [C12Mim] [Alg], it is yellow at room temperature
Color solid.
Example 8:1- methyl -3- myristyl imidazoles alginate ionic liquids [C14mim][Alg].5.93g will be contained
The aqueous isopropanol of (0.020mol) 1- methyl -3- myristyl imidazolium hydroxides is with containing 3.87g (0.022mol) marine alga
The brand-new aqueous solution (solvent swelling state) mixing of acid, after stirring 24 hours at room temperature, carries out centrifugal treating to it and takes out clear liquid, remove
Go after solvent to obtain 1- methyl -3- myristyl imidazoles alginate ionic liquids [C14Mim] [Alg], it is yellow at room temperature
Color solid.
Example 9:1- methyl -3- cetyl imidazoles alginate ionic liquids [C16mim][Alg].6.49g will be contained
The aqueous isopropanol of (0.020mol) 1- methyl -3- cetyl imidazolium hydroxides is with containing 3.87g (0.022mol) marine alga
The brand-new aqueous solution (solvent swelling state) of acid is mixed, and after being stirred 48 hours at 75 DEG C, is carried out centrifugal treating to it and is taken out clear liquid, remove
Go after solvent to obtain 1- methyl -3- cetyl imidazoles alginate ionic liquids [C16Mim] [Alg], it is yellow at room temperature
Color solid.
Example 10:1- methyl -3- octadecyl imidazoles alginate ionic liquids [C18mim][Alg].7.05g will be contained
The aqueous isopropanol of (0.020mol) 1- methyl -3- octadecyl imidazolium hydroxides is with containing 3.87g (0.022mol) marine alga
The brand-new aqueous solution (solvent swelling state) of acid is mixed, and after being stirred 72 hours at 75 DEG C, is carried out centrifugal treating to it and is taken out clear liquid, remove
Go after solvent to obtain 1- methyl -3- octadecyl imidazoles alginate ionic liquids [C18Mim] [Alg], it is yellow at room temperature
Color solid.
Example 11:1- methyl -3- allyl imidazole alginate ionic liquids [Amim] [Alg].2.80g will be contained
The aqueous isopropanol of (0.020mol) 1- methyl -3- allyl imidazole hydroxide is with containing 3.52g (0.022mol) alginic acid
The brand-new aqueous solution (solvent swelling state) mixing, at room temperature stir 8 hours after, centrifugal treating is carried out to it and clear liquid is taken out, remove
1- methyl -3- allyl imidazole alginate ionic liquids [Amim] [Alg] are obtained after solvent, it is that yellow is consolidated at room temperature
Body.
Example 12:1- methyl -3- acetonyl imidazoles alginate ionic liquids [MeCOCH2mim][Alg].It will contain
The aqueous isopropanol of 3.12g (0.020mol) 1- methyl -3- acetonyl imidazolium hydroxides is with containing 3.87g (0.022mol) seas
The brand-new aqueous solution (solvent swelling state) mixing of alginic acid, after stirring 24 hours at room temperature, carries out centrifugal treating to it and takes out clear liquid,
1- methyl -3- acetonyl imidazoles alginate ionic liquids [MeCOCH is obtained after removing solvent2Mim] [Alg], it is at room temperature
It is light yellow solid.
Example 13:1- methyl -3- cyanoethyl imidazoles alginate ionic liquids [NCCH2mim][Alg].2.78g will be contained
The aqueous isopropanol of (0.020mol) 1- methyl -3- cyanoethyl imidazolium hydroxides is with containing 3.87g (0.022mol) alginic acid
The brand-new aqueous solution (solvent swelling state) mixing, at room temperature stir 24 hours after, centrifugal treating is carried out to it and clear liquid is taken out, remove
Formed after solvent and obtain 1- methyl -3- cyanoethyl imidazoles alginate ionic liquids [NCCH2Mim] [Alg], it is at room temperature
Light yellow solid.
Example 14:1- methyl -3- ethyl acetate base imidazoles alginate ionic liquids [CH3CH2OOCCH2mim][Alg]。
By the aqueous isopropanol containing 3.72g (0.020mol) 1- methyl -3- ethyl acetate base imidazolium hydroxides with containing 3.87g
The brand-new aqueous solution (solvent swelling state) mixing of (0.022mol) alginic acid, after stirring 24 hours at room temperature, is carried out at centrifugation to it
Manage and take out clear liquid, remove after solvent, obtain 1- methyl -3- ethyl acetate base imidazoles alginate ionic liquids
[CH3CH2OOCCH2Mim] [Alg], it is yellow viscous liquid at room temperature.
Example 15:1- methyl -3- acetenyl imidazoles alginate ionic liquids [HCCH2mim][Alg].2.52g will be contained
The aqueous isopropanol of (0.020mol) 1- methyl -3- acetenyl imidazolium hydroxides is with containing 3.87g (0.022mol) alginic acid
The brand-new aqueous solution (solvent swelling state) mixing, at room temperature stir 48 hours after, centrifugal treating is carried out to it and clear liquid is taken out, remove
1- methyl -3- acetenyl imidazoles alginate ionic liquids [HCCH is obtained after solvent2Mim] [Alg], it is yellow at room temperature
Thick liquid.
Example 16:1- ethyl -3- butyl imidazole alginate ionic liquids [C2C4im][Alg].3.41g will be contained
The aqueous isopropanol of (0.020mol) 1- ethyl -3- butyl imidazole hydroxide is with containing 3.87g (0.022mol) alginic acid
The brand-new aqueous solution (solvent swelling state) is mixed, and after stirring 12 hours at room temperature, is carried out centrifugal treating to it and is taken out clear liquid, is removed molten
1- ethyl -3- butyl imidazole alginate ionic liquids [C is obtained after agent2C4Im] [Alg], it is yellow solid at room temperature.
Example 17:1- propyl group -3- butyl imidazole alginate ionic liquids [C3C4im][Alg].3.69g will be contained
The aqueous isopropanol of (0.020mol) 1- propyl group -3- butyl imidazole hydroxide is with containing 3.87g (0.022mol) alginic acid
The brand-new aqueous solution (solvent swelling state) is mixed, and after stirring 12 hours at room temperature, is carried out centrifugal treating to it and is taken out clear liquid, is removed molten
1- propyl group -3- butyl imidazole alginate ionic liquids [C is obtained after agent3C4Im] [Alg], it is yellow solid at room temperature.
Example 18:1,2- dibutyl imidazoles alginate ionic liquids [C4C4im][Alg].3.97g will be contained
The aqueous isopropanol of (0.020mol) 1,2- dibutyl imidazolium hydroxides and the brand-new containing 3.87g (0.022mol) alginic acid
The aqueous solution (solvent swelling state) is mixed, and after stirring 24 hours at room temperature, is carried out centrifugal treating to it and is taken out clear liquid, is removed after solvent
Obtain 1,2- dibutyl imidazoles alginate ionic liquids [C4C4Im] [Alg], it is light yellow solid at room temperature.
Example 19:1- butyl -3- amyl group imidazoles alginate ionic liquids [C4C5im][Alg].4.25g will be contained
The aqueous isopropanol of (0.020mol) 1- butyl -3- amyl group imidazolium hydroxides is with containing 3.87g (0.022mol) alginic acid
The brand-new aqueous solution (solvent swelling state) is mixed, and after stirring 24 hours at room temperature, is carried out centrifugal treating to it and is taken out clear liquid, is removed molten
1- butyl -3- amyl group imidazoles alginate ionic liquids [C is obtained after agent4C5Im] [Alg], it is light yellow solid at room temperature.
Example 20:1- butyl -3- hexyl imidazolium alginate ionic liquids [C4C6mim][Alg].4.53g will be contained
The aqueous isopropanol of (0.020mol) 1- butyl -3- hexyl imidazolium hydroxide is with containing 3.87g (0.022mol) alginic acid
The brand-new aqueous solution (solvent swelling state) is mixed, and after stirring 24 hours at room temperature, is carried out centrifugal treating to it and is taken out clear liquid, is removed molten
1- butyl -3- hexyl imidazolium alginate ionic liquids [C is obtained after agent4C6Mim] [Alg], it is yellow solid at room temperature.
Example 21:1,2,3- tri-methylimidazolium alginate ionic liquids [C1mmim][Alg].2.56g will be contained
The aqueous isopropanol of (0.020mol) 1,2,3- tri-methylimidazolium hydroxide is with containing the new of 3.87g (0.022mol) alginic acid
The aqueous solution (solvent swelling state) mixing processed, after stirring 12 hours at room temperature, carries out centrifugal treating to it and takes out clear liquid, remove solvent
After obtain 1,2,3- tri-methylimidazolium alginate ionic liquids [C1Mmim] [Alg], it is light yellow solid at room temperature.
Example 22:1,2- dimethyl -3- ethyl imidazol(e) alginate ionic liquids [C2mmim][Alg].2.84g will be contained
The aqueous isopropanol of (0.020mol) 1,2- dimethyl -3- ethyl imidazol(e) hydroxide is with containing 3.87g (0.022mol) marine alga
The brand-new aqueous solution (solvent swelling state) mixing of acid, after stirring 12 hours at room temperature, carries out centrifugal treating to it and takes out clear liquid, remove
Go after solvent to obtain 1,2- dimethyl -3- ethyl imidazol(e) alginate ionic liquids [C2Mmim] [Alg], it is yellow at room temperature
Color solid.
Example 23:1,2- dimethyl -3- propyl imidazole alginate ionic liquids [C3mmim][Alg].3.12g will be contained
The aqueous isopropanol of (0.020mol) 1,2-dimethyl-3- propyl imidazole hydroxide is with containing 3.87g (0.022mol) marine alga
The brand-new aqueous solution (solvent swelling state) mixing of acid, after stirring 24 hours at room temperature, carries out centrifugal treating to it and takes out clear liquid, remove
Go after solvent to obtain 1,2- dimethyl -3- propyl imidazole alginate ionic liquids [C3Mmim] [Alg], it is yellow at room temperature
Color solid.
Example 24:1,2- dimethyl -3- butyl imidazole alginate ionic liquids [C4mmim][Alg].3.41g will be contained
The aqueous isopropanol of (0.020mol) 1,2- dimethyl -3- butyl imidazole hydroxide is with containing 3.87g (0.022mol) marine alga
The brand-new aqueous solution (solvent swelling state) mixing of acid, after stirring 24 hours at room temperature, carries out centrifugal treating to it and takes out clear liquid, remove
Go after solvent to obtain 1,2- dimethyl -3- butyl imidazole alginate ionic liquids [C4Mmim] [Alg], it is yellow at room temperature
Color solid.
Described above is only the preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
For member, without departing from the technical principles of the invention, some improvement and modification can also be made, these improvement and modification
Also it should be regarded as protection scope of the present invention.
Claims (9)
1. a kind of imidazoles alginate ionic liquid, it is characterised in that:The structural formula of the imidazoles alginate ion is:
Wherein R1、R3For H atom, alkyl or substituted hydrocarbon radical;R2For H atom or methyl;[Alg]—For marine alga acid radical anion.
2. a kind of imidazoles alginate ionic liquid according to claim 1, it is characterised in that:Described alkyl is
Carbon chain lengths are 1~20 alkyl.
3. a kind of imidazoles alginate ionic liquid according to claim 1, it is characterised in that:Described substitution hydrocarbon
Base is methyl, ethyl, propyl group, butyl, amyl group, hexyl, octyl group, decyl, dodecyl, myristyl, cetyl, octadecane
Any one in base, pi-allyl, acetonyl, cyanoethyl, ethyl acetate base, acetenyl.
4. a kind of synthetic method of imidazoles alginate ionic liquid, it is characterised in that comprise the following steps:By imidazoles hydrogen
Oxide is with brand-new alginic acid according to 1:1~1.1 mol ratio is mixed in a solvent, is stirred, and reaction terminates rear centrifuging and taking
Go out clear liquid, and remove solvent, you can obtain imidazoles alginate ionic liquid.
5. a kind of synthetic method of imidazoles alginate ionic liquid according to claim 4, it is characterised in that:It is molten
Agent can select any one or a few in water, dichloroethanes, isopropanol.
6. a kind of synthetic method of imidazoles alginate ionic liquid according to claim 5, it is characterised in that:Institute
The solvent stated is water or isopropanol.
7. a kind of synthetic method of imidazoles alginate ionic liquid according to claim 4, it is characterised in that:Instead
Answer temperature for room temperature to 75 DEG C.
8. a kind of synthetic method of imidazoles alginate ionic liquid according to claim 7, it is characterised in that:Instead
It is room temperature to answer temperature.
9. a kind of synthetic method of imidazoles alginate ionic liquid according to claim 4, it is characterised in that:
Mixed in solvent, the time for stirring and reacting is 1~72 hour.
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CN114606508A (en) * | 2022-03-16 | 2022-06-10 | 四川大学 | Environment-friendly ionic liquid degreasing fluid and using method thereof |
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CN109942395B (en) * | 2019-03-29 | 2021-09-21 | 四川大学 | Curcumin ionic liquid and application thereof |
CN114606508A (en) * | 2022-03-16 | 2022-06-10 | 四川大学 | Environment-friendly ionic liquid degreasing fluid and using method thereof |
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