CN110054731A - A kind of preparation method of the maleimide copolymer of reversible soda acid mutagens color - Google Patents
A kind of preparation method of the maleimide copolymer of reversible soda acid mutagens color Download PDFInfo
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- CN110054731A CN110054731A CN201910388057.6A CN201910388057A CN110054731A CN 110054731 A CN110054731 A CN 110054731A CN 201910388057 A CN201910388057 A CN 201910388057A CN 110054731 A CN110054731 A CN 110054731A
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- reversible
- maleimide
- soda acid
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- mutagens color
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—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 carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/36—Amides or imides
- C08F222/40—Imides, e.g. cyclic imides
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/02—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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a single or double bond to nitrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—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 carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/36—Amides or imides
- C08F222/40—Imides, e.g. cyclic imides
- C08F222/408—Imides, e.g. cyclic imides substituted imides comprising other heteroatoms
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Abstract
The invention discloses a kind of preparation methods of the maleimide copolymer of reversible soda acid mutagens color, belong to Polymer Synthesizing and applied technical field.The above method includes: step 1: a certain proportion of maleimide (NMIs), diallyl dimethyl amine (MDAA) and azodiisobutyronitrile (AIBN) being taken to be placed in reaction vessel; then solvent is added; stirring, vacuumizes, and then reacts a period of time under nitrogen protection；Step 2: after reaction, the reaction product in above-mentioned steps 1 being transferred in bag filter and is dialysed, is then centrifuged, be dried in vacuo, obtain the polymer containing different functional groups maleimide.The present invention is prepared for the functional material of soda acid mutagens color, and through analyzing, copolymer has outstanding Reversible Cycle stability, with good application prospect.
Description
Technical field
The present invention relates to Polymer Synthesizing and applied technical fields, and in particular to a kind of Malaysia acyl of reversible soda acid mutagens color
The preparation method of imine copolymer.
Background technique
Invertible switch functional material is in data storage, sensor, color monitor, building and building, health care, storage
The practical application potentiality in the fields such as device keep its of increasing concern.Since the 1980s, the hair of invertible switch functional material
It opens up the switching characteristic sensitive to environmental response, stimulation and proposes great requirement.It is most in these invertible switch functional materials
Number contains organic principle, and reversible switching can be carried out under continued stimulus.However, some organic moieties may be toxic, solid-state like
Velocity variations are slow under state, and undergo aging and degradation by lasting outside stimulus (such as ultraviolet light irradiation).It is all these to ask
Topic significantly limits their practical application.Although producing stable reversible functional material to meet growing global need
It asks and has important practical significance, but remain the lot of challenges such as stability and cost in practical applications.
Summary of the invention
In view of the deficiency of the prior art, the object of the present invention is to provide a kind of Malaysia acyls of reversible soda acid mutagens color
The preparation method of imine copolymer.The technology of the present invention conjugated polymer has preferable stability characteristic, excellent hydrophobic performance
Deng and maleimide five-membered ring be greatly improved the thermal stability of polymer the characteristics of synthesized a kind of novel Malaysia acyl
Imine copolymer, and it is prepared for it functional material of soda acid mutagens color, through analyzing, copolymer has outstanding Reversible Cycle steady
It is qualitative, with good application prospect.
In order to solve the above technical problems, present invention offer technical solution is as follows:
The present invention provides a kind of preparation method of the maleimide copolymer of reversible soda acid mutagens color, comprising:
Step 1: take a certain proportion of maleimide, diallyl dimethyl amine and azodiisobutyronitrile to be placed in reaction vessel,
Then solvent is added, stirs, vacuumizes, then reacts a period of time under nitrogen protection；
Step 2: after reaction, the reaction product in above-mentioned steps 1 is transferred in bag filter and is dialysed, is then centrifuged,
Vacuum drying, obtains the polymer containing different functional groups maleimide.
In the step 1, the maleimide, diallyl dimethyl amine and azodiisobutyronitrile molar ratio are as follows: 1:1:
0.02。
Further, in the step 1, solvent DMF, dosage is the 1%-30% of monomer gross mass.
Further, in the step 1, reaction condition is 65-80 DEG C, reacts 10-20 h.
Further, in the step 2, the parameter of bag filter: 2000 g/mol, dialysis time 10-72h.
Further, in the step 2, centrifugal condition 5000-10000 r/min is centrifuged 2-10 min.
Further, in the step 2, it is dried in vacuo 30-60 DEG C of condition, dry 10-24 h.
The synthetic reaction equation of above-mentioned maleimide copolymer is as follows:
Wherein: R is cyclohexyl (CH), phenyl (Ph), 4- trifluoromethyl (TFMPh) or 2,4,6- trichlorophenyls (TCPh).
The invention has the following advantages:
In the present invention, copolymer is made into certain density solution, solvent DMF is formed and is had coloured clear solution, when to
When acid being added in liquid, the ketonic oxygen in polymer architecture can be combined with Hydrogen Proton, form enol-type structure, solution is made to become nothing
Color, when continuing that triethylamine is added into solution, amide proton can be combined with the nitrogen in diallyl dimethyl amine five-membered ring, carbonyl
Electronics transfer occurs for base oxygen, forms enolate formula structure, color is caused to be restored.
The technology of the present invention conjugated polymer has preferable stability characteristic, excellent hydrophobic performance etc. and maleimide
Amine five-membered ring is greatly improved the characteristics of thermal stability of polymer and has synthesized a kind of novel maleimide copolymer, is used in combination
Its functional material for being prepared for soda acid mutagens color, through analyzing, copolymer has outstanding Reversible Cycle stability, has preferable
Application prospect.
Detailed description of the invention
Fig. 1 is gel permeation chromatography (GPC) figure of the maleimide copolymer of 1-4 of embodiment of the present invention preparation；
Fig. 2 is the nucleus magnetic hydrogen spectrum figure of the maleimide copolymer of 1-4 of embodiment of the present invention preparation；
Fig. 3 is maleimide copolymer stability analysis figure prepared by the embodiment of the present invention 3.
Specific embodiment
It, below will knot to keep the embodiment of the present invention technical issues that need to address, technical solution and advantage clearer
Specific embodiments and the drawings are closed to be described in detail.But the present invention is limited to absolutely not these examples.It is as described below be only the present invention compared with
Good embodiment is only used to explain the present invention, and it cannot be understood as the limitations of the invention patent range.It should be understood that
, any modifications, equivalent replacements and improvementsmade within the spirit and principles of the invention, etc. should be included in this hair
Within bright protection scope.Therefore, the scope of protection of the patent of the invention shall be subject to the appended claims.
Agents useful for same is commercial product unless otherwise specified in following embodiment.
The invention proposes a kind of preparation method of the maleimide copolymer of reversible soda acid mutagens color, illustrate as
Under.
Embodiment 1
A kind of preparation method of the maleimide copolymer of reversible soda acid mutagens color, comprising:
Step 1: taking molar ratio is that N-cyclohexylmaleimide, diallyl dimethyl amine and the azodiisobutyronitrile of 1:1:0.02 is set
In reaction vessel, 1% DMF solution of above-mentioned three kinds of monomer gross mass is then added, is uniformly mixed, vacuumizes, then
65 DEG C under nitrogen protection, react 20 h；
Step 2: after reaction, the reaction product in above-mentioned steps 1 is transferred in bag filter and is dialysed, the parameter of bag filter:
2000 g/mol, dialysis time 10h；Then 10000 r/min are centrifuged 8 min, and 60 DEG C of 10 h of vacuum drying are obtained containing not
With the polymer of functional group's maleimide.
Embodiment 2
A kind of preparation method of the maleimide copolymer of reversible soda acid mutagens color, comprising:
Step 1: taking molar ratio is that phenyl maleimide, diallyl dimethyl amine and the azodiisobutyronitrile of 1:1:0.02 is placed in
In reaction vessel, 10% DMF solution of above-mentioned three kinds of monomer gross mass is then added, is uniformly mixed, vacuumizes, then
80 DEG C under nitrogen protection, react 10h；
Step 2: after reaction, the reaction product in above-mentioned steps 1 is transferred in bag filter and is dialysed, the parameter of bag filter:
2000 g/mol, dialysis time 72h；Then 5000 r/min are centrifuged 10 min, and 30 DEG C of 24 h of vacuum drying are obtained containing not
With the polymer of functional group's maleimide.
Embodiment 3
A kind of preparation method of the maleimide copolymer of reversible soda acid mutagens color, comprising:
Step 1: taking molar ratio is 4- trifluoromethyl maleimide, diallyl dimethyl amine and the azo two of 1:1:0.02
Isobutyronitrile is placed in reaction vessel, and 20% DMF solution of above-mentioned three kinds of monomer gross mass is then added, is uniformly mixed, and is taken out
Vacuum, reacts 15h by then under nitrogen protection 70 DEG C；
Step 2: after reaction, the reaction product in above-mentioned steps 1 is transferred in bag filter and is dialysed, the parameter of bag filter:
2000 g/mol, dialysis time 36h；Then 70000 r/min are centrifuged 8 min, and 40 DEG C of vacuum drying 16h are obtained containing not
With the polymer of functional group's maleimide.
Embodiment 4
A kind of preparation method of the maleimide copolymer of reversible soda acid mutagens color, comprising:
Step 1: taking molar ratio is 2,4,6- trichlorophenyl maleimides, diallyl dimethyl amine and the azo two of 1:1:0.02
Isobutyronitrile is placed in reaction vessel, and 30% DMF solution of above-mentioned three kinds of monomer gross mass is then added, is uniformly mixed, and is taken out
Vacuum, reacts 18h by then under nitrogen protection 75 DEG C；
Step 2: after reaction, the reaction product in above-mentioned steps 1 is transferred in bag filter and is dialysed, the parameter of bag filter:
2000 g/mol, dialysis time 48h；Then 80000 r/min are centrifuged 5min, 50 DEG C of 18 h of vacuum drying, obtain containing difference
The polymer of functional group's maleimide.
To the gel permeation chromatography of the maleimide copolymer of the reversible soda acid mutagens color of above-described embodiment 1-4 preparation
(GPC) it analyzes, sees Fig. 1.As can be seen from Figure, there is a peak in 4 kinds of polymer, this obtained polymer is one
Kind substance, without impurity or other polymers.In addition, obtained polymer appearance time is longer, illustrate the molecule of polymer
Amount is the level of oligomer, obtains the molecular weight ranges of 4 kinds of polymer after tested in 1400-2500g/mol, and molecular weight distribution
Close to 1.00, it was demonstrated that the present invention successfully prepares the maleimide copolymer of reversible soda acid mutagens color.
And the carry out nuclear-magnetism inspection of the maleimide copolymer to the reversible soda acid mutagens color of above-described embodiment 1-4 preparation
It surveys, as a result sees Fig. 2.Solvent for use is deuterated chloroform, and as shown in Figure 2, chemical shift is MDAA in 2.875 ppm and 3.783ppm
The absorption peak for the methyl being connected in structure with N element, the absorption for the methylene being connected at 3.25 to 4.32 ppm with N element
Peak.This demonstrate that there is the presence of MDAA in polymer.Chemical shift arrives 1.87ppm 1.04, is the cyclohexyl Central Asia at 3.85ppm
The absorption peak of methyl, phenyl, trifluoromethyl, trichlorophenyl chemical shift such as Fig. 2 h, i, j, arrived positioned at 6.86
7.98ppm place.Further prove that the present invention successfully prepares the maleimide copolymer of reversible soda acid mutagens color.
The cyclical stability of the maleimide copolymer of the reversible soda acid mutagens color of the preparation of above-described embodiment 4 is examined
It surveys, as a result sees Fig. 3.Fig. 3 is the uv-vis spectra after ten circulations, by can see in figure, after 10 circulations,
The absorbance of polymer illustrates that polymer has preferable stability there is no reducing.
In summary, novel maleimide copolymer prepared by the present invention has outstanding Reversible Cycle stability,
With good application prospect.
The above is a preferred embodiment of the present invention, it is noted that for those skilled in the art
For, without departing from the principles of the present invention, it can also make several improvements and retouch, these improvements and modifications
It should be regarded as protection scope of the present invention.
Claims (7)
1. a kind of preparation method of the maleimide copolymer of reversible soda acid mutagens color characterized by comprising
Step 1: taking a certain proportion of maleimide (NMIs), diallyl dimethyl amine (MDAA) and azodiisobutyronitrile
(AIBN) it is placed in reaction vessel, solvent is then added, stir, vacuumize, then react a period of time under nitrogen protection；
Step 2: after reaction, the reaction product in above-mentioned steps 1 is transferred in bag filter and is dialysed, is then centrifuged,
Vacuum drying, obtains the polymer containing different functional groups maleimide.
2. the preparation method of the maleimide copolymer of reversible soda acid mutagens color according to claim 1, feature exist
In, in the step 1, the maleimide, diallyl dimethyl amine and azodiisobutyronitrile molar ratio are as follows: 1:1:0.02.
3. the preparation method of the maleimide copolymer of reversible soda acid mutagens color according to claim 2, feature exist
In in the step 1, solvent DMF, dosage is the 1%-30% of monomer gross mass.
4. the preparation method of the maleimide copolymer of reversible soda acid mutagens color according to claim 3, feature exist
In in the step 1, reaction condition is 65-80 DEG C, reacts 10-20 h.
5. the preparation method of the maleimide copolymer of reversible soda acid mutagens color according to claim 1, feature exist
In, in the step 2, the parameter of bag filter: 2000-4000 g/mol, dialysis time 10-72h.
6. the preparation method of the maleimide copolymer of reversible soda acid mutagens color according to claim 5, feature exist
In in the step 2, centrifugal condition 5000-10000 r/min is centrifuged 2-10 min.
7. the preparation method of the maleimide copolymer of reversible soda acid mutagens color according to claim 6, feature exist
In, in the step 2,30-60 DEG C of condition of vacuum drying, dry 10-24 h.
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| CN201910388057.6A CN110054731B (en) | 2019-05-10 | 2019-05-10 | Preparation method of reversible acid-base discoloration maleimide copolymer |
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Inventor after: Zhang Shuxiang Inventor after: Di Congcong Inventor after: Zhao Yaodong Inventor after: Li Tianyu Inventor after: Zhang Luqing Inventor after: Zong Chuanyong Inventor after: Zhang Yabin Inventor after: Xu Lin Inventor before: Zhang Shuxiang Inventor before: Di Congcong Inventor before: Zhao Yaodong |
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