CN110343242A - Photochromic hyperbranched azopolyamide of one kind and preparation method thereof - Google Patents
Photochromic hyperbranched azopolyamide of one kind and preparation method thereof Download PDFInfo
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- CN110343242A CN110343242A CN201910600051.0A CN201910600051A CN110343242A CN 110343242 A CN110343242 A CN 110343242A CN 201910600051 A CN201910600051 A CN 201910600051A CN 110343242 A CN110343242 A CN 110343242A
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
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Abstract
The present invention provides photochromic hyperbranched azopolyamide of one kind and preparation method thereof, with 4,4'- chrysoidine, trimesic acid is raw material, trimesic acid is converted to pyromellitic trimethylsilyl chloride first, then passes through low-temperature solution polycondensation synthesis of super branched azopolyamide using acid chloride groups and the reactivity of amino.The thermodynamic stability and excellent processing performance for making the optical activity of its existing azo group, and having polamides good, and using the photo-isomerisable characteristic and photic trans- suitable isomerization dynamics of UV-Vis spectral investigation synthesis azobenzene polymer.
Description
Technical field
The present invention relates to chemical high molecular materials to study preparation field, and in particular to a kind of photochromic hyperbranched azo
Polyamide and preparation method thereof.
Background technique
Dissaving polymer is a kind of highly branched poly- with three-dimensional dimension dendritic structure and a large amount of molecule internal pores
Object is closed, with its unique structure, excellent performance becomes the research hotspot of chemical field.With dendritic phase
There is no dendritic macromole regular than, the geometric shape of dissaving polymer, be in quasi-spherical molecule structure, molecular weight distribution compared with
Width, geometric isomer is more, but it have with dendritic similar characteristic, if viscosity is low, dissolubility height etc., furthermore it form a film
Property it is good, synthesis technology is simple, at low cost, is conducive to large-scale production, therefore there is dissaving polymer important theoretical research to anticipate
Justice simultaneously has broad application prospects.
Azo polymer is hot spot studied both at home and abroad at present as a kind of novel photoelectric information functional material, by
In its excellent photo-isomerisable, the optical activities such as Photo alignment make it in optical information storage, photoelectronics, molecular switch, liquid
The fields such as brilliant material, nonlinear optical material have vast application prospect.
Electrostatic in many factors for influencing the photic trans- suitable isomery effect of azobenzene polymer, between azobenzene group dipole
Interaction is one of principal element, it is known that azobenzene polymer photic trans- suitable isomery effect it is inefficient so that its light
It is also not significant enough to learn performance, and the machining property of known azobenzene polymer and thermal stability are poor, overcome these resistances
Hinder, just makes azobenzene polymer that there can be practical efficient purposes on photoelectric information functional material.
Summary of the invention
The object of the present invention is to provide a kind of with the photic of preferable optical property, thermal stability and machining property
The hyperbranched azopolyamide and preparation method thereof of discoloration.
The present invention provides a kind of photochromic hyperbranched azopolyamide, structural formula is as follows:
Wherein, the weight average molecular weight Mw=4250 of the hyperbranched azopolyamide, molecular weight distribution D=1.70.This hair
Bright another object is to provide a kind of preparation method of photochromic hyperbranched azopolyamide, includes the following steps:
S1: the thionyl chloride of trimesic acid and 100ml that concentration is 0.10mol is added in the first flask, then drips
Flask is carried out oil bath, flask is made to be to slowly warm up to 75 DEG C by the catalyst added, under the protection of catalyst, carries out 10 hours
Reaction after, the liquid in flask is cooled to room temperature, first air-distillation goes out the unreacted thionyl chloride of system, then depressurizes again
Distillation obtains pyromellitic trimethylsilyl chloride；
S2: under the conditions of ice bath and nitrogen atmosphere, pyromellitic trimethylsilyl chloride and lithium chloride are added in the second flask, and be dissolved in
In 2.0mL dry solvent n,N-dimethylacetamide, stirring dissolves it sufficiently, after reaction in 30 minutes, respectively plus
The bis- amido azobenzene of acid binding agent pyridine and suitable 4,4'- for entering 0.06mL, is stirred, after the reaction of 2 hours, by flask
It is taken out from ice bath, is placed in after reacting 12 hours under room temperature, reaction solution is poured under stiring by anhydrous methanol and water
It in the mixed liquor of composition, stands precipitation precipitating and obtains filter cake, gained filter cake uses methanol, water washing respectively, carries out centrifugation, together
After the method for sample separates 3 to 5 times, in pressure be 0.08kPa and temperature is dry 64 hours in 60 DEG C of vacuum ovens, is obtained
Hyperbranched azopolyamide.
Preferably, the catalyst is n,N-Dimethylformamide.
Preferably, the catalyst of the dropwise addition is 1ml.
Preferably, the quality for the trimesic acid being added in flask is 21 grams, the equal benzene being evaporated under reduced pressure
Three formyl chlorides are 26 grams.
Preferably, in the mixed liquor, the volumetric ratio of anhydrous methanol and water is 1:1.
Preferably, three formyl chloride of benzene being added in the second flask is 0.125 gram, the chlorine being added in the second flask
Changing lithium is 0.03 gram.
Preferably, the dosage of 4,4'-, the bis- amido azobenzene according to acid chloride groups in reactant pyromellitic trimethylsilyl chloride with
Amino molar ratio N in 4,4'- chrysoidine-COCl/N-NH2Amount determined.
Preferably, first flask and the second flask are three mouthfuls of burnings equipped with reflux condensing tube and HCl reception device
Bottle.
Preferably, first flask and the second flask can be the same three-necked flask.
Beneficial effects of the present invention:
The present invention provides a kind of photochromic hyperbranched azopolyamide, and azo group is introduced into dissaving polymer
The middle optical Response for forming the new functional hyperbranched azobenzene polymer of one kind and both having there is azobenzene chromophore, at the same it is hyperbranched big
The architectural characteristic of molecule assigns its special photoelectric properties, thermal stability and good machining property.
Detailed description of the invention
The present invention will be further described with reference to the accompanying drawings, but the embodiment in attached drawing is not constituted to any limit of the invention
System, for those of ordinary skill in the art, without creative efforts, can also obtain according to the following drawings
Other attached drawings.
Fig. 1 is the structural formula of photochromic hyperbranched azopolyamide of one kind of the invention and preparation method thereof；
Fig. 2 is monomer 4 of the invention, 4'- chrysoidine (AZDA), pyromellitic trimethylsilyl chloride (BTC), hyperbranched azo
Polyamide HBAPE5 infrared spectrum；
Fig. 3 is the gpc analysis result of HBAPE5 of the invention；
Fig. 4 is the thermal analysis curve of synthesis of super branched azopolyamide HBAPE5 of the invention；
The N- first that Fig. 5 is monomer AZDA of the invention, the concentration of polymer HBAPE2 and HBAPE5 are 1.0 × 10-5g/ml
Base pyrrolidones nmp solution, the ultraviolet-visible spectrum changed through λ=365nm ultraviolet light, absorption spectrum with light application time
Figure；
Fig. 6 is the At/A0~t curve of AZDA, HBAPE2 and HBAPE5 of the invention in nmp solution；
Fig. 7 is the photic trans cis Isomerization first order kinetics curve of HBAPE2 of the invention in different solvents；
Fig. 8 is AZDA, HBAPE2 and HBAPE5 of the invention photic trans cis Isomerization first order kinetics curve in NMP.
Specific embodiment
The invention will be further described with the following Examples.
The invention will be further described with the following Examples.Photochromic hyperbranched azo polyamides of the present embodiment
Amine, as shown in Figure 1, the structural formula of hyperbranched azopolyamide, the hyperbranched azopolyamide is macromolecular structure.It is described super
The optical activity of branching azopolyamide (following abbreviation HBAPE) existing azo group, and the heating power for having polamides good
Learn stability and excellent processing performance.
Photochromic hyperbranched azopolyamide is prepared by the following preparation method:
S1: in the three-necked flask equipped with reflux condensing tube and HCl reception device, it is 0.10mol's that 21 grams of concentration, which are added,
The thionyl chloride of trimesic acid and 100ml, is then added dropwise the n,N-Dimethylformamide of 1ml as catalyst, by flask into
Row oil bath makes flask be to slowly warm up to 75 DEG C,, will be in flask after the reaction for carrying out 10 hours under the protection of catalyst
Liquid is cooled to room temperature, and first air-distillation goes out the unreacted thionyl chloride of system, is then evaporated under reduced pressure to obtain 26 grams of equal benzene again
Three formyl chlorides (following abbreviation BTC).Pyromellitic trimethylsilyl chloride product is white crystal, and yield is about 98%.
S2: be added under the conditions of ice bath and nitrogen atmosphere, in three-necked flask 0.125 gram pyromellitic trimethylsilyl chloride and 0.03 gram
Lithium chloride, and be dissolved in the dry solvent n,N-dimethylacetamide of 2.0mL, stirring dissolved it sufficiently, by 30 minutes
After reaction, it is separately added into the acid binding agent pyridine and bis- amido azobenzene of suitable 4,4'- (following abbreviation AZDA) of 0.06mL, is carried out
Stirring, after the reaction of 2 hours, flask is taken out from ice bath, is placed in after reacting 12 hours under room temperature, by reaction solution
It is poured into the mixed liquor being made of anhydrous methanol and water under stiring, stands precipitation precipitating and obtain filter cake, gained filter cake is used respectively
Methanol, water washing carry out centrifugation, and after same method separates 3 to 5 times, in pressure be 0.08kPa and temperature is 60 DEG C true
Dry 64 hours, obtain hyperbranched azopolyamide in empty drying box.
Preferably, in the mixed liquor, the volumetric ratio of anhydrous methanol and water is 1:1.
Preferably, the dosage of 4,4'-, the bis- amido azobenzene according to acid chloride groups in reactant pyromellitic trimethylsilyl chloride with
Amino molar ratio N in 4,4'- chrysoidine-COCl/N-NH2Amount determined.It is as shown in Table 1:
Table one is acid chloride groups and amino molar ratio N in 4,4'- chrysoidine in three formyl chloride of benzene-COCl/N-NH2And
The number of the hyperbranched azopolyamide of synthesis:
As shown in Fig. 2, as can be seen that hyperbranched azopolyamide HBAPE5 is in 3339cm from spectrogram-1There are secondary acyls at place
The stretching vibration peak of amine N-H；In 1667cm-1There is the stretching vibration peak of amide Ⅰ carbonyl C=O in secondary amide in place；?
1519cm-1There is in-plane bending vibration peak of the amide II with N-H in place.4,4'- chrysoidine AZDA is in 3474cm-1With
3376cm-1There is the stretching vibration peak of primary amide N-H in place；Pyromellitic trimethylsilyl chloride BTC is in 1764cm-1There is C=O and stretches in place
Contracting vibration peak.Comprehensive Correlation can obtain that polymer has synthesized and fundamental reaction is complete.
As shown in figure 3, the weight average molecular weight Mw=4250 of HBAPE5, molecular weight distribution D=1.70.
As shown in figure 4, when temperature rises to about 300 DEG C, polyamide about weightlessness 10%, it can thus be appreciated that the polyamide tool of synthesis
There is preferable thermal stability.
Shown in Fig. 5, with the extension of light application time, the absorption peak of HBAPE2 and HBAPE5 in 386nm and 384nm is (trans-
π-π * the transition of azo group) gradually weaken, and the absorption peak (the n- π * transition of cis- azo group) near 510nm gradually increases
By force, and variation tendency is smaller and smaller to being no longer changed, and illustrates that trans- suitable isomerization reaction has occurred in system under ultraviolet lighting
And it is finally reached the balance (photostationary state) of cis-trans-isomer, compared with azo monomer, the maximum absorption wavelength of polymer is had occurred
Violet shift.HBAPE2 is at 343nm and 480nm in wavelength simultaneously, and HBAPE5 is that appearance etc. is inhaled at 340nm and 476nm in wavelength
Point illustrates that the cis-trans isomerization that azo primitive only has occurred under illumination condition reacts, and the generation without other side reactions.
If A0, At, A ∞ are respectively through λ=365nm ultraviolet light, before illumination (t=0), illumination t moment and illumination
In maximum absorption wavelength λ when to stable state (t=∞)maxThe absorbance at place.With λmaxThe absorbance value at place tracks suitable, anti-azobenzene
First component ratio, At/A0 indicate percentage contents of the trans-azobenzene primitive in stock blend in polymer architecture.With At/A0
It maps to light application time t, At/A0 value is smaller, i.e. isomery conversion ratio is bigger.As shown in fig. 6, the conversion of polymer isomerization reaction
Rate is much larger than the conversion ratio of monomer, is because forming the intermolecular hydrogen bonding declines after polyamide between solvent, isomerization is anti-
It should be easier to, isomerisation conversion increases.
It is ultraviolet if cis-trans isomerization reaction is that first order kinetics react according to principle of dynamics and langbobier law
Spectral absorbance changes, ln [(A0-A ∞)/(At-A ∞)]=Kp × t, with ln [(A0-A in a linear relationship with light application time
∞)/(At-A ∞)] it maps to time t, then the slope of straight line is isomerization reaction rate constant Kp.As shown in fig. 7, its is different
Descending structure reaction rate constant is Kp (THF) > Kp (C3H6O) > Kp (NMP), this is because with aprotic solvent pole
Property increase, between azobenzene polymer and aprotic solvent dipole-dipole effect increase, hinder its trans- clockwiseization, so as to cause
Kp becomes smaller.As shown in figure 8, the isomerization reaction speed ratio monomer that can obtain polymer from figure is big, this is because synthetic polymer
The intermolecular hydrogen bonding effect that N-H key is formed in the amide group of formation, solvent and polymer segment is than-NH2 in solvent and monomer
The hydrogen bond action of formation wants small, then hinders cis-trans isomerization movement that will reduce, isomerization reaction rate accordingly just will increase；Together
When HBAPE2 isomerization reaction speed ratio HBAPE5 it is big because in synthetic polymer azobenzene structure unit increase, surpass
The branched structure of branching molecule can provide a free volume in its intramolecule for azobenzene group, make azobenzene group phase
Mutually aggregation is difficult, and each azobenzene group efficiently separates it is avoided that or reducing azobenzene group electrostatic work occurring between each other
With and effective azobenzene group concentration is reduced, to improve photoisomerization reaction rate.It is described under specific illumination,
The rate of hyperbranched azopolyamide photoisomerization reaction can be realized the process of preferable optical storage and removing, pass through this light
Performance is learned, the hyperbranched azopolyamide has boundless prospect in the application of optical material.
Described with 4,4'- chrysoidine, trimesic acid acid is raw material, is synthesized by low-temperature solution polycondensation super
Branching azopolyamide, weightlessness 10% when temperature be about 300 DEG C, have preferable thermal stability.Ultra-violet analysis shows through λ=
365nm ultraviolet light, violet shift has occurred compared with monomer in the maximum absorption wavelength of polymer, while polymer is anti-along different
Structure reaction rate is bigger than the rate of monomer, and reduces with the polar increase of organic solvent.
Photochromic hyperbranched azopolyamide of the present invention and preparation method thereof is described in detail above, herein
In apply that a specific example illustrates the principle and implementation of the invention.The explanation of above example is only intended to sides
Assistant solves core of the invention thought；At the same time, for those skilled in the art, according to the thought of the present invention, specific
There will be changes in embodiment and application range, in conclusion the content of the present specification should not be construed as to of the invention
Limitation.
Claims (10)
1. a kind of photochromic hyperbranched azopolyamide, which is characterized in that its structural formula is as follows:
Wherein, the weight average molecular weight Mw=4250 of the hyperbranched azopolyamide, molecular weight distribution D=1.70.
2. a kind of preparation method of photochromic hyperbranched azopolyamide as described in claim 1, which is characterized in that system
Preparation Method includes the following steps:
S1: the trimesic acid and 100ml thionyl chloride that concentration is 0.10mol are added in the first flask, what is be then added dropwise urges
Flask is carried out oil bath, flask is made to be to slowly warm up to 75 DEG C by agent, under the protection of catalyst, carries out the reaction of 10 hours
Afterwards, the liquid in flask is cooled to room temperature, first air-distillation goes out the unreacted thionyl chloride of system, is then evaporated under reduced pressure to again
To pyromellitic trimethylsilyl chloride；
S2: under the conditions of ice bath and nitrogen atmosphere, pyromellitic trimethylsilyl chloride and lithium chloride are added in the second flask, and it is dry to be dissolved in 2.0mL
In dry solvent n,N-dimethylacetamide, stirring dissolves it sufficiently, after reaction in 30 minutes, is separately added into 0.06mL
Bis- amido azobenzene of acid binding agent pyridine and suitable 4,4'-, be stirred, after the reaction of 2 hours, by flask from ice bath
It takes out, is placed in after reacting 12 hours under room temperature, reaction solution is poured under stiring and is mixed by what anhydrous methanol and water formed
It closes in liquid, stands precipitation precipitating and obtain filter cake, gained filter cake uses methanol, water washing respectively, carries out centrifugation, same method
After separation 3 to 5 times, in pressure be 0.08kPa and temperature is dry 64 hours in 60 DEG C of vacuum ovens, obtains hyperbranched idol
Nitrogen polyamide.
3. a kind of photochromic hyperbranched azopolyamide as claimed in claim 2 and preparation method thereof, which is characterized in that
The catalyst is N,N-dimethylformamide.
4. a kind of photochromic hyperbranched azopolyamide as claimed in claim 2 and preparation method thereof, which is characterized in that
The catalyst of the dropwise addition is 1ml.
5. a kind of photochromic hyperbranched azopolyamide as claimed in claim 2 and preparation method thereof, which is characterized in that
The quality that the trimesic acid in the first flask is added is 21 grams, and the pyromellitic trimethylsilyl chloride being evaporated under reduced pressure is 26
Gram.
6. a kind of photochromic hyperbranched azopolyamide as claimed in claim 2 and preparation method thereof, which is characterized in that
In the mixed liquor, the volumetric ratio of anhydrous methanol and water is 1:1.
7. a kind of photochromic hyperbranched azopolyamide as claimed in claim 2 and preparation method thereof, which is characterized in that
Three formyl chloride of benzene being added in the second flask is 0.125 gram, and the lithium chloride being added in the second flask is 0.03 gram.
8. a kind of photochromic hyperbranched azopolyamide as claimed in claim 2 and preparation method thereof, which is characterized in that
The dosage of the bis- amido azobenzene of 4,4'- is according to acid chloride groups in reactant pyromellitic trimethylsilyl chloride and 4,4'- diamino azo
Amino molar ratio N in benzene-COCl/N-NH2Amount determined.
9. a kind of photochromic hyperbranched azopolyamide as claimed in claim 2 and preparation method thereof, which is characterized in that
First flask and the second flask are the three-necked flask equipped with reflux condensing tube and HCl reception device.
10. a kind of photochromic hyperbranched azopolyamide as claimed in claim 9 and preparation method thereof, feature exists
In first flask and the second flask can be the same three-necked flask.
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| CN112745731A (en) * | 2021-01-19 | 2021-05-04 | 敬青梅 | Hyperbranched polymer-containing waterborne antifouling composite coating and preparation method thereof |
| CN113354808A (en) * | 2020-03-06 | 2021-09-07 | 武汉纺织大学 | Spirooxazine-based photochromic polyamide material and preparation method thereof |
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Application publication date: 20191018 |