CN107778482A - The preparation and application of the triazine contracting terephthalaldehyde polyShiff base molysite of 2 chlorine, 4,6 diaminourea 1,3,5 - Google Patents
The preparation and application of the triazine contracting terephthalaldehyde polyShiff base molysite of 2 chlorine, 4,6 diaminourea 1,3,5 Download PDFInfo
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- CN107778482A CN107778482A CN201710876852.0A CN201710876852A CN107778482A CN 107778482 A CN107778482 A CN 107778482A CN 201710876852 A CN201710876852 A CN 201710876852A CN 107778482 A CN107778482 A CN 107778482A
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- terephthalaldehyde
- contracting
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- triazines
- molysite
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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
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
- C08G73/0644—Poly(1,3,5)triazines
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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
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
- C08G73/065—Preparatory processes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
Abstract
The invention discloses a kind of preparation and application of the triazine contracting terephthalaldehyde polyShiff base molysite of 2 chlorine, 4,6 diaminourea 1,3,5.（1）With terephthalaldehyde and the triazine contracting terephthalaldehyde of 2 chlorine, 4,6 diaminourea 1,3,5 for raw material, in N, N dimethylformamides, using glacial acetic acid as catalyst, it is heated to reflux, obtain the triazine contracting terephthalaldehyde contracting terephthalaldehyde polyShiff base of 2 chlorine, 4,6 diaminourea 1,3,5；（2）The triazine contracting terephthalaldehyde contracting terephthalaldehyde polyShiff base of 2 chlorine, 4,6 diaminourea 1,3,5 and ferric trichloride are raw material, in N, N dimethylformamide, it is heated to reflux, obtains 2 chlorine 4, the triazine contracting terephthalaldehyde contracting terephthalaldehyde polyShiff base molysite of 6 diaminourea 1,3,5.Raw material of the present invention is easy to get, cheap, prepares simplicity, gained polyShiff base and its molysite are respectively provided with good absorbing property.
Description
Technical field
The invention belongs to absorbing material field, more particularly to a kind of chloro- 4,6- diamino-1,3,5-triazines contractings of 2- are to benzene two
The preparation and application of formaldehyde polyShiff base molysite.
Background technology
Absorbing material is constantly in very important status in current military, it by the energy of electromagnetic wave absorption, from
And converted, energy attenuation in another form reaches stealthy purpose.For from loss mechanism, mainly there is resistance
Loss, dielectric loss and magnetic loss, but be difficult to there is a kind of material to meet all of above wave-absorbing mechanism simultaneously, therefore prepare compound
The absorbing material of type meets that some electromagnetic performances are a nowadays very important research directions as much as possible；From absorbing property
On from the point of view of, different absorbing material absorbing properties is also not quite similar, but widens frequency range and the enhancing of the following reflection losses of -10dB
The maximum of reflection loss is the common research direction of current scientist.
Organic absorbing material is easily-synthesized, light specific gravity, stability are good, is easy to the features such as regulation, is extremely potential one
Class absorbing material.N is easy to and transition-metal coordination in C=N double bonds in schiff bases, passes through and changes chain in conjugation schiff base structure
The approach such as length, heteroatomic species or the different type of substituent, thus it is possible to vary the reason of schiff bases and its metal complex
Change property.Document shows that conjugated compound has the potential for inhaling ripple.
Conduction high polymer is the insulating polymer of a kind of main chain altogether, is carried out by the method for chemistry or electrochemistry and dopant
Doping, change backbone structure, due to that can be led with big pi-electron conjugated system, its electrical conductivity in insulator, semiconductor and metal
Change between body.Its density is small, structure diversity, electromagnetic parameter is adjustable, stability is good, and numerous good characteristics have caused extensively
General attention.
The content of the invention
It is an object of the invention to provide a kind of chloro- 4, the 6- diamino-1,3,5-triazines contracting terephthalaldehyde polyShiff bases of 2-
The preparation method and application of molysite absorbing material.
Prepare chloro- 4, the 6- diamino-1,3,5-triazines contracting terephthalaldehyde polyShiff base molysite absorbing materials of above-mentioned 2-
Concretely comprise the following steps：
(1) chloro- 4, the 6- diamino-1,3,5-triazines of 0.01mol (1.46g) 2-, 0.01mol (1.34g) are weighed to benzene two
Formaldehyde and 50mL analyze pure DMF (DMF) solution, are put into 250mL round-bottomed flasks, and 2~3 drop analyses are added dropwise
Pure glacial acetic acid (being used as catalyst), the lower magnetic agitation of nitrogen protection is simultaneously gradually heating to 140 DEG C, reacted 10 hours, molten in flask
Liquid is changed into pale red transparency liquid from colourless, and after stopping reaction, natural cooling is down to room temperature, and the reaction solution into flask adds dropwise
Enter 150mL deionized water, now there are a large amount of pale red Precipitations, filtered after standing 1~2 hour, take filter cake, use deionization
Water and absolute ethyl alcohol washing, to remove unreacted raw material and DMF solvent, dry in 60 DEG C of vacuum drying chamber, produce 2-
Chloro- 4,6- diamino-1,3,5-triazines contracting terephthalaldehyde polyShiff base light red solid powder (being designated as L9)；
(2) by chloro- 4, the 6- diamino-1,3,5-triazines contracting terephthalaldehyde polyShiff bases (L9) of 2- obtained by step (1)
Pure DMF (DMF) is analyzed with 10mL to dissolve, then is transferred in round-bottomed flask, and being warming up to 80 DEG C can all dissolve.
(3) chloro- 4, the 6- diamino-1,3,5-triazines contracting terephthalaldehyde polyShiff bases (L9) of 2- as obtained by step (1)
With FeCl3Mol ratio is to weigh FeCl at 1: 23, it is completely dissolved in 15mL and analyzes in pure DMF (DMF).
(4) will be slowly dropped into constant pressure funnel obtained by step (3) in the round-bottomed flask for filling step (2) gains, after
Continuous to be heated to reflux simultaneously magnetic agitation 8 hours, solution is changed into dark-brown from pale red in flask, after reaction stops, cooling down to room
Temperature, the solution in flask is added dropwise in water and recrystallized, to remove unreacted FeCl3, DMF
(DMF) filter after, standing 1~2 hour, and filter cake is washed with absolute methanol, obtained solid matter is put into 50 DEG C
In vacuum drying chamber, chloro- 4, the 6- diamino-1,3,5-triazines contracting terephthalaldehyde polyShiff base molysite (being designated as C9) of 2- are produced.
It is right in 2-18GHz frequency ranges using the U.S. (Hewlett-Packard) Agilent company N5230C type vector network analyzers
PolyShiff base compound and its iron complex carry out electromagnetic parameter (ε `, ε ``, μ `, μ ``) and tested, the results showed that the present invention
Chloro- 4, the 6- diamino-1,3,5-triazines contracting terephthalaldehyde polyShiff base molysite of 2- there is preferable absorbing property, can apply
In absorbing material field.
Present invention design has synthesized chloro- 4, the 6- diamino-1,3,5-triazines contracting terephthalaldehyde polyShiff base molysite of 2- and inhaled
Wave material.This conjugated poly-schiff base is because its molecule chain rigidity is strong, and intermolecular force is big, heat-resist, and raw material is easy to get, price
It is cheap, simplicity is prepared, reaction condition is gentle.
Brief description of the drawings
Fig. 1 is chloro- 4, the 6- diamino-1,3,5-triazines contracting terephthalaldehyde polyShiff bases of 2- in the embodiment of the present invention
(L9) infrared spectrum analysis figure.
Fig. 2 is the iron of chloro- 4, the 6- diamino-1,3,5-triazines contracting terephthalaldehyde polyShiff bases of 2- in the embodiment of the present invention
The infrared spectrum analysis figure of salt (C9).
Fig. 3 is chloro- 4, the 6- diamino-1,3,5-triazines contracting terephthalaldehyde polyShiff base electromagnetism of 2- in the embodiment of the present invention
The test result figure of parameter (ε `, ε ``, μ `, μ ``), wherein：A- complex dielectric permittivities real part ε ` and frequency graph of a relation；B- is situated between again
Electric constant imaginary part ε `` and frequency graph of a relation；C- complex permeability real part μ ` and frequency graph of a relation；D- complex permeability imaginary part μ ``
With the graph of a relation of frequency.
Fig. 4 be the embodiment of the present invention in the chloro- 4,6- diaminostilbenes of 2-, 3,5- triazine contracting terephthalaldehyde polyShiff base iron
The test result figure of salt electromagnetic parameter (ε `, ε ``, μ `, μ ``), wherein：A- complex dielectric permittivities real part ε ` and frequency graph of a relation；
B- complex dielectric permittivities imaginary part ε `` and frequency graph of a relation；C- complex permeability real part μ ` and frequency graph of a relation；D- complex permeability
Imaginary part μ `` and frequency graph of a relation.
Fig. 5 is the anti-of chloro- 4, the 6- diamino-1,3,5-triazines contracting terephthalaldehyde polyShiff bases of 2- in the embodiment of the present invention
Penetrate damage curve.
Fig. 6 is the iron of chloro- 4, the 6- diamino-1,3,5-triazines contracting terephthalaldehyde polyShiff bases of 2- in the embodiment of the present invention
The reflection loss curve of salt.
Embodiment
With reference to specific embodiment, the present invention is furture elucidated, but embodiment is not intended to limit protection scope of the present invention.
Embodiment：
Prepare the specific of chloro- 4, the 6- diamino-1,3,5-triazines contracting terephthalaldehyde polyShiff base molysite absorbing materials of 2-
Step is：
(1) chloro- 4, the 6- diamino-1,3,5-triazines of 0.01mol (1.46g) 2-, 0.01mol (1.34g) are weighed to benzene two
Formaldehyde and 50mL analyze pure DMF (DMF) solution, are put into 250mL round-bottomed flasks, and 3 drops are added dropwise and analyze pure ice
Acetic acid (is used as catalyst), and the lower magnetic agitation of nitrogen protection is simultaneously gradually heating to 140 DEG C, reacts 10 hours, in flask solution by
Colourless to be changed into pale red transparency liquid, after stopping reaction, natural cooling is down to room temperature, and the reaction solution into flask is added dropwise
150mL deionized water, now there is a large amount of pale red Precipitations, is filtered after standing 1 hour, takes filter cake, with deionized water and
Absolute ethyl alcohol washs, and to remove unreacted raw material and DMF solvent, is dried in 60 DEG C of vacuum drying chamber, it is chloro- to produce 2-
4,6- diamino-1,3,5-triazines contracting terephthalaldehyde polyShiff base light red solid powder (being designated as L9, yield 91%), its is red
External spectrum is shown in Fig. 1.
(2) by chloro- 4, the 6- diamino-1,3,5-triazines contracting terephthalaldehyde polyShiff bases (L9) of 2- obtained by step (1)
Pure DMF (DMF) is analyzed with 10mL to dissolve, then is transferred in round-bottomed flask, and being warming up to 80 DEG C can all dissolve.
(3) chloro- 4, the 6- diamino-1,3,5-triazines contracting terephthalaldehyde polyShiff bases (L9) of 2- as obtained by step (1)
With FeCl3Mol ratio is to weigh FeCl at 1: 23, it is completely dissolved in 15mL and analyzes in pure DMF (DMF).
(4) will be slowly dropped into constant pressure funnel obtained by step (3) in the round-bottomed flask for filling step (2) gains, after
Continuous to be heated to reflux simultaneously magnetic agitation 8 hours, solution is changed into dark-brown from pale red in flask, after reaction stops, cooling down to room
Temperature, the solution in flask is added dropwise in water and recrystallized, to remove unreacted FeCl3, DMF
(DMF) filter after, standing 1 hour, and filter cake is washed with absolute methanol, obtained solid matter is put into 50 DEG C of vacuum
In drying box, chloro- 4, the 6- diamino-1,3,5-triazines contracting terephthalaldehyde polyShiff base molysite (being designated as C9) of 2- are produced, its is red
External spectrum is shown in Fig. 2.
Synthetic route is：
The present invention uses the U.S. (Hewlett-Packard) Agilent company N5230C type vector network analyzers, in 2-18GHz frequency models
In enclosing, electromagnetic parameter (ε `, ε ``, μ `, μ ``) is carried out to polyShiff base compound and its iron complex and tested, as a result sees figure
3 and Fig. 4.Preparation of samples：Heating paraffin is melted, powder to be measured is added with 5: 5 ratio (volume ratio), is stirred and with surpassing
Sound wave disperses, and in press-in mould preheated in advance, the ring-type external diameter of coaxial sample is 7mm, internal diameter 3mm, thickness 2mm.
According to transmission line theory, reflection loss (RL) of the individual layer microwave absorbing coating in electromagnetic wave vertical incidence can be by following
Formula be calculated：
RL (dB)=201g | (Zin-Z0)/(Zin+Z0)|
In formula, Zin is the input impedance of microwave absorbing coating, Z0It is the wave impedance of free space, μrAnd εrRespectively microwave absorbing coating
Complex permeability and complex dielectric permittivity, d be material thickness, f is the frequency of incident electromagnetic wave, and c is the light velocity.RL values be equal to-
10dB means 90% microwave absorbability, so RL≤- 10dB generally is regarded as into a material if appropriate for as electromagnetic wave
One important evidence of absorbent.Thickness 2.5-5.0mm microwave absorbing coating by surveyed electromagnetic parameters and is obtained according to formula
Reflection loss curve in the range of 2-18GHz, is as a result shown in Fig. 5 and Fig. 6.It was found from figure, 2- chloro- 4 in the range of 2-18GHz,
6- diaminostilbenes, 3,5- triazine contracting terephthalaldehyde polyShiff bases and its molysite proportion of goods damageds respectively up to -3.725dB, -
11.26dB。
The research table of absorbing property is carried out to the polyShiff base compound and its molysite of synthesis using vector network analyzer
Bright, in the range of 2-18GHz, after polyShiff base compound is coordinated with metal salt, it inhales ripple electromagnetic property relative to polyShiff base
Compound is itself improved, and the reflection loss of molysite is substantially more much higher than polyShiff base compound itself.
Claims (2)
1. a kind of chloro- 4,6- diaminostilbenes of 2-, the synthesis side of 3,5- triazine contracting terephthalaldehyde polyShiff base molysite absorbing materials
Method, it is characterised in that concretely comprise the following steps：
(1) the chloro- 4,6- diaminostilbenes of 1.46 g 2- are weighed, 3,5- triazines, 1.34 g terephthalaldehydes and 50 mL analyses are pure
DMF solution, it is put into 250 mL round-bottomed flasks, 2 ~ 3 drops is added dropwise and analyze pure glacial acetic acid, under nitrogen protection
Magnetic agitation is simultaneously gradually heating to 140 DEG C, reacts 10 hours, and solution is changed into pale red transparency liquid from colourless in flask, stops
After reaction, natural cooling is down to room temperature, and 150 mL deionized water is added dropwise in the reaction solution into flask, now has a large amount of light
Red precipitate separates out, and is filtered after standing 1 ~ 2 hour, takes filter cake, washed with deionized water and absolute ethyl alcohol, done in 60 DEG C of vacuum
Dried in dry case, produce chloro- 4, the 6- diamino-1,3,5-triazines contracting terephthalaldehyde polyShiff base light red solid powder of 2-；
(2) by the chloro- 4,6- diaminostilbenes of 2- obtained by step (1), 3,5- triazines contracting terephthalaldehyde polyShiff base is with 10mL points
Pure DMF dissolving is analysed, then is transferred in round-bottomed flask, is warming up to 80 DEG C；
(3) the chloro- 4,6- diaminostilbenes of 2- as obtained by step (1), 3,5- triazines contracting terephthalaldehyde polyShiff base and FeCl3Rub
You are than being 1:2 weigh FeCl3, it is completely dissolved in 15mL and analyzes in pure DMF；
(4) it will be slowly dropped into constant pressure funnel obtained by step (3) in the round-bottomed flask for filling step (2) gains, and continue to add
Hot simultaneously magnetic agitation 8 hours of flowing back, solution is changed into dark-brown from pale red in flask, after reaction stops, cooling down to room temperature, by
Solution in flask, which is added dropwise in water, to be recrystallized, and is filtered after standing 1 ~ 2 hour, and filter cake is washed with absolute methanol
Wash, obtained solid matter is put into 50 DEG C of vacuum drying chambers, produce chloro- 4, the 6- diamino-1,3,5-triazines contractings of 2- to benzene
Dicarbaldehyde polyShiff base molysite.
2. the chloro- 4,6- diaminostilbenes of 2- according to claim 1,3,5- triazines contracting terephthalaldehyde polyShiff base and molysite
Application, it is characterised in that chloro- 4, the 6- diamino-1,3,5-triazines contracting terephthalaldehyde polyShiff base of the 2- and molysite inhale ripple
It is functional, -3.725 dB, -11.26 dB are reached respectively in 2-18 GHz range internal losses rate, can apply to absorbing material neck
Domain.
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| CN201710876852.0A CN107778482A (en) | 2017-09-25 | 2017-09-25 | The preparation and application of the triazine contracting terephthalaldehyde polyShiff base molysite of 2 chlorine, 4,6 diaminourea 1,3,5 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111234214A (en) * | 2020-04-02 | 2020-06-05 | 南昌航空大学 | Triazine-based Schiff base conjugated microporous polymer and preparation method thereof |
| CN117488307A (en) * | 2023-11-03 | 2024-02-02 | 东莞市德硕化工有限公司 | Metal surface treating agent and preparation method thereof |
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| CN111234214A (en) * | 2020-04-02 | 2020-06-05 | 南昌航空大学 | Triazine-based Schiff base conjugated microporous polymer and preparation method thereof |
| CN111234214B (en) * | 2020-04-02 | 2022-05-27 | 南昌航空大学 | Triazine-based Schiff base conjugated microporous polymer and preparation method thereof |
| CN117488307A (en) * | 2023-11-03 | 2024-02-02 | 东莞市德硕化工有限公司 | Metal surface treating agent and preparation method thereof |
| CN117488307B (en) * | 2023-11-03 | 2024-04-16 | 东莞市德硕化工有限公司 | Metal surface treating agent and preparation method thereof |
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