CN104327276A - Cross-linking type polyphosphazene-based organic dye selective adsorbent and preparation method thereof - Google Patents
Cross-linking type polyphosphazene-based organic dye selective adsorbent and preparation method thereof Download PDFInfo
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- CN104327276A CN104327276A CN201410470179.7A CN201410470179A CN104327276A CN 104327276 A CN104327276 A CN 104327276A CN 201410470179 A CN201410470179 A CN 201410470179A CN 104327276 A CN104327276 A CN 104327276A
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Abstract
The invention provides a cross-linking type polyphosphazene-based organic dye selective adsorbent and a preparation method thereof, and belongs to the technical field of adsorbent function materials. The preparation method of the adsorbent comprises the following steps: Step 1, in the presence of an acid-binding agent, hexachlorocyclotriphosphazene and comonomer undergo condensation polymerization in an organic solvent, so as to obtain a solution; and Step 2, solid products in the solution are separated, washed and dried, so as to obtain the adsorbent. The preparation process of the cross-linking type polyphosphazene-based organic dye selective adsorbent is simple and mild. The cross-linking type polyphosphazene-based organic dye selective adsorbent has unique capacity of selectively adsorbing and separating organic cationic dye and organic dye with proton H in the chemical structure, has high adsorption capacity, is suitable for sewage treatment in the field of environmental protection, and is beneficial to realize industrial production.
Description
Technical field
The present invention relates to a class organic dye adsorbent namely, specifically a class is based on the organic dye selective adsorbent of ring cross-linking type poly phosphazene.Such sorbent material has unique selective adsorption and separating power to the organic dye in Cationic organic dyes and chemical structure with proton H, and loading capacity is large.The invention further relates to the preparation method of described sorbent material.The invention belongs to sorbent material class technical field of function materials.
Technical background
In the past in many decades, organic dye has been widely used in the various fields such as papermaking, food, makeup, textiles, medicine, printing and leather.But most of organic dye all has toxicity and non-biodegradable, its unreasonable discharge can produce serious harm to environment and affect the health of the mankind.Therefore, how quickly and efficiently the organic dye be separated in waste water has become one of focus of current field of environment protection research.
The separation method that in the aqueous solution, organic dye is conventional has sedimentation, membrane sepn, ion-exchange, oxidation, adsorbent, biological treatment and photochemical catalysis etc., wherein adsorbent have efficiently, the advantage such as low cost, easy and simple to handle, recoverable, be the focus that industry member and academia pay close attention to always.All kinds of sorbent materials developed at present mainly comprise gac, potter's clay, zeolite, chitosan, red soil and wastes of crops etc.Although these traditional sorbent materials can organic dye in active adsorption aqueous phase, but scarcely possesses selective adsorption and the ability be separated.Realize not only there is environment protection significance to the selective adsorption of organic dye, and for detecting and identifying that specific dyestuff has practical significance.Therefore, exploration has selective adsorption and has important research value with the Novel adsorption agent material being separated organic dye function.
Synthetic polymer, because having excellent molecular structure designability, is considered to the optimal object of preparation selective adsorption agent material.By introducing specific functional group in polymer architecture, and there is host-guest interactions between dye molecule, as electrostatic attraction, hydrogen bond, pi-pi accumulation, hydrophobic interaction and soda acid interaction etc., the selective adsorption to organic dye in aqueous phase can be realized.Through finding the literature search of prior art, Britain's " materials chemistry magazine " periodical is in the 22nd volume in 2012 10055th ~ 10061 pages of (S.Deng, R.Wang, H.Xu, X.Jiang, J.Yin, Hybrid hydrogels of hyperbranched poly (ether amine) s (hPEAs) for selective adsorption of guest molecules and separation of dyes, Journal of Material Chemistry, 2012, 22, 10055-10061) report a kind of hyperbranched polyetheramine hybridized hydrogel, the selective adsorption to organic dye is realized by hydrophobic interaction.The U.S.'s " physical chemistry impurity, C collects " periodical is in the 114th volume in 2010 14377th ~ 14383 pages of (M.M.Ayad, A.A.El-Nasr, Adsorption of cationic dye (methylene blue) from water using polyaniline nanotubes base, Journal of Physical Chemistry C, 2010,114,14377-14383) report using polyaniline nanotube as sorbent material, utilize the amino in aniline and the electrostatic interaction between imino-and methylene blue positively charged ion, by methylene blue fractionation by adsorption from the aqueous solution.Although the synthetic polymer sorbent material reported above-mentioned can carry out selective adsorption effectively to organic dye and be separated, and preparation process is often comparatively loaded down with trivial details, and loading capacity is not high, limits its mass-producing application.
Summary of the invention
The object of the invention is to overcome the deficiencies in the prior art, provide a class based on organic dye selective adsorbent of ring cross-linking type poly phosphazene and preparation method thereof.The present invention is with hexachlorocyclotriphosphazene and bisphenols or the aromatic diamines comonomer method by an one-step polycondensation, and prepare the hybrid inorganic-organic sorbent material that a class has highly cross-linked structure, preparation process is simply gentle.Prepared sorbent material has unique selective adsorption and separating power to the organic dye in Cationic organic dyes and chemical structure with proton H, and loading capacity is large, be applicable to the sewage disposal of field of Environment Protection, be conducive to realizing suitability for industrialized production, have broad application prospects.
The present invention is achieved by the following technical solutions, and the present invention relates to the organic dye selective adsorbent of a class based on ring cross-linking type poly phosphazene, its chemical structure is as follows:
Wherein R is bisphenols or aromatic diamines comonomer structural unit.
The preparation method of described sorbent material, comprises the steps:
Step one, under the existence of acid binding agent, gets hexachlorocyclotriphosphazene and comonomer in organic solvent polycondensation occurs, obtains solution;
Step 2, the solid product in separation solution, washing is also dry, obtains sorbent material.
In step one, described acid binding agent is the one in triethylamine, Tributylamine, pyridine, salt of wormwood.
In step, described comonomer is bisphenols or aromatic diamines organic compound, such as bisphenol S, bisphenol AF, dihydroxyphenyl propane, bisphenol fluorene, curcumine, p-diaminodiphenyl, 4,4 '-diaminodiphenyl oxide, 4,4 '-diaminodiphenylmethane etc., but the present invention is not limited to the scope of above-mentioned citing.
In step one, the mol ratio of described hexachlorocyclotriphosphazene and comonomer is 1:3.
In step one, described organic solvent is acetonitrile, acetone, toluene, tetrahydrofuran (THF), N, the mixed solvent of one or more in N '-dimethyl methane amide.
In step one, described polycondensation actual conditions is: be under the ultrasonication of 50 ~ 300 watts at power, 30 ~ 60 DEG C of water-baths 3 ~ 8 hours.
Compared with prior art, the present invention has following beneficial effect: the preparation method of (1) sorbent material of the present invention is quick, simple and gentle; (2) sorbent material of the present invention has unique highly cross-linked hybrid inorganic-organic structure, gives thermostability and the chemical stability of its excellence.(3) nitrogen-atoms with lone-pair electron is rich in the structure of sorbent material of the present invention, interacted by soda acid, can effectively realize to the selective adsorption of the organic dye in Cationic organic dyes and chemical structure with proton H be separated, and loading capacity is large, has a good application prospect.
Accompanying drawing explanation
Fig. 1 is synthetic route and the chemical structure schematic diagram of the sorbent material that embodiment 1 obtains;
Fig. 2 is the Fourier transform infrared spectroscopy figure of the sorbent material that embodiment 1 obtains;
Fig. 3 is the electron scanning micrograph of the sorbent material that embodiment 1 obtains;
Fig. 4 is the digital photograph (a: before absorption of the organic dye in the obtained adsorbent aqueous phase of embodiment 1; B: adsorb after 48 hours).
Embodiment
Following instance will the invention will be further described by reference to the accompanying drawings.The present embodiment is implemented under premised on technical solution of the present invention, gives detailed embodiment and process, but protection scope of the present invention is not limited to following embodiment.The experimental technique of unreceipted actual conditions in the following example, usually conveniently condition, or according to the condition that manufacturer advises.
Embodiment 1
In the round-bottomed flask containing 0.40g hexachlorocyclotriphosphazene, 0.87g bisphenol S (mol ratio of hexachlorocyclotriphosphazene and bisphenol S is 1:3) and 100mL acetonitrile, add 1mL triethylamine, ultrasonic in the water-bath of 50 DEG C (power is 200W) reacts 3 hours.After reaction terminates, centrifugal except desolventizing, centrifuge speed 8000 revs/min, the time is 5 minutes.Use acetone and deionized water wash product 2 times respectively, then the dry hybrid inorganic-organic sorbent material obtaining white powder for 24 hours in 40 DEG C of vacuum drying ovens.
The implementation result of the present embodiment: Fig. 1 is synthetic route and the chemical structure schematic diagram of sorbent material.Under the condition of acid binding agent made by triethylamine, there is an one-step polycondensation reaction, obtain highly cross-linked organic-inorganic hybrid polymer sorbent material in hexachlorocyclotriphosphazene and bisphenol S, the hydrogenchloride simultaneously produced is absorbed by triethylamine and forms triethylamine hydrochloride.
Fig. 2 is the Fourier transform infrared spectroscopy figure of the sorbent material of preparation.As seen from the figure, 1585cm is positioned at
-1(a) and 1487cm
-1b the absorption peak of () is the characteristic peak of phenyl ring; 1290cm
-1(c) and 1181cm
-1d the absorption peak of () belongs to the stretching vibration of O=S=O; 1145cm
-1(e) and 881cm
-1f the absorption peak of () belongs to P=N and P-N respectively; 3250 ~ 3500cm
-1g () is the characteristic peak of phenolic hydroxyl group, disappear after polycondensation terminates; Meanwhile, at 934cm
-1h () place creates a new absorption peak, it is the characteristic peak of P-O-(Ph).Therefore, infrared spectrum demonstrates between hexachlorocyclotriphosphazene and bisphenol S and there occurs polycondensation.
Fig. 3 is the electron scanning micrograph of the sorbent material of preparation.As shown in the figure, the sorbent material of preparation has good ball-type microstructure, and particle diameter is comparatively homogeneous, and median size is about 550nm.
Fig. 4 for the sorbent material got successively prepared by 10mg join respectively starting point concentration be 100 μMs orange G, Ponceau S, tropeolin-D, fluorexon, rhodamine B, bismark brown Y, methylene blue and toluylene red the aqueous solution in, vibration absorption 48 hours, the digital photograph comparison diagram before and after absorption.Can find out, prepared sorbent material has selective adsorption behavior to bismark brown Y, toluylene red, methylene blue, rhodamine B and fluorexon, utilizes uv-visible absorption spectra analysis to obtain saturated extent of adsorption and is respectively 119.27,116.73,93.08,56.06 and 11.30mg g
-1, and to orange G, Ponceau S and tropeolin-D almost without absorption, prove the organic dye in the alternative Liquidity limit organic dye of this sorbent material and chemical structure with proton H.
Embodiment 2
In the round-bottomed flask containing 0.20g hexachlorocyclotriphosphazene, 0.58g bisphenol AF (mol ratio of hexachlorocyclotriphosphazene and bisphenol AF is 1:3) and 100mL acetonitrile, add 4mL triethylamine, ultrasonic in the water-bath of 50 DEG C (power is 200W) reacts 6 hours.After reaction terminates, centrifugal except desolventizing, centrifuge speed 8000 revs/min, the time is 5 minutes.Use acetone and deionized water wash product 2 times respectively, then the dry hybrid inorganic-organic sorbent material obtaining white powder for 24 hours in 40 DEG C of vacuum drying ovens.
Embodiment 3
In the round-bottomed flask containing 0.20g hexachlorocyclotriphosphazene, 0.60g bisphenol fluorene (mol ratio of hexachlorocyclotriphosphazene and bisphenol fluorene is 1:3) and 100mL acetonitrile, add 4mL triethylamine, ultrasonic in the water-bath of 50 DEG C (power is 200W) reacts 6 hours.After reaction terminates, centrifugal except desolventizing, centrifuge speed 8000 revs/min, the time is 5 minutes.Use acetone and deionized water wash product 2 times respectively, then the dry hybrid inorganic-organic sorbent material obtaining white powder for 24 hours in 40 DEG C of vacuum drying ovens.
Embodiment 4
In the round-bottomed flask containing 0.20g hexachlorocyclotriphosphazene, 0.64g curcumine (mol ratio of hexachlorocyclotriphosphazene and curcumine is 1:3) and 100mL acetonitrile, add 4mL triethylamine, ultrasonic in the water-bath of 50 DEG C (power is 200W) reacts 7 hours.After reaction terminates, centrifugal except desolventizing, centrifuge speed 8000 revs/min, the time is 5 minutes.Use acetone and deionized water wash product several times respectively, until centrifugal rear supernatant liquid is colourless, the then dry hybrid inorganic-organic sorbent material obtaining yellow powder for 24 hours in 40 DEG C of vacuum drying ovens.
Claims (7)
1. a class is based on the organic dye selective adsorbent of ring cross-linking type poly phosphazene, it is characterized in that, its chemical structure is as follows:
Wherein R is bisphenols or aromatic diamines comonomer structural unit.
2. the preparation method of the class organic dye selective adsorbent based on ring cross-linking type poly phosphazene according to claim 1, is characterized in that, comprise the steps:
Step one, under the existence of acid binding agent, gets hexachlorocyclotriphosphazene and comonomer in organic solvent polycondensation occurs, obtains solution;
Step 2, the solid product in separation solution, washing is also dry, obtains sorbent material.
3. a class according to claim 2 is based on the preparation method of the organic dye selective adsorbent of ring cross-linking type poly phosphazene, it is characterized in that, in step one, described acid binding agent is the one in triethylamine, Tributylamine, pyridine, salt of wormwood.
4. a class according to claim 2 is based on the preparation method of the organic dye selective adsorbent of ring cross-linking type poly phosphazene, it is characterized in that, in step one, described comonomer is bisphenols or aromatic diamines organic compound.
5. a class according to claim 2 is based on the preparation method of the organic dye selective adsorbent of ring cross-linking type poly phosphazene, it is characterized in that, in step one, the mol ratio of described hexachlorocyclotriphosphazene and comonomer is 1:3.
6. a class according to claim 2 is based on the preparation method of the organic dye selective adsorbent of ring cross-linking type poly phosphazene, it is characterized in that, in step, described organic solvent is acetonitrile, acetone, toluene, tetrahydrofuran (THF), N, the mixed solvent of one or more in N '-dimethyl methane amide.
7. a class according to claim 2 is based on the preparation method of the organic dye selective adsorbent of ring cross-linking type poly phosphazene, it is characterized in that, in step one, described polycondensation actual conditions is: be under the ultrasonication of 50 ~ 300 watts at power, 30 ~ 60 DEG C of water-baths 3 ~ 8 hours.
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| CN108129666A (en) * | 2018-01-15 | 2018-06-08 | 西北工业大学 | Multi-metal oxygen cluster basic ring crosslinked poly-phosphine nitrile hybrid high polymer material and preparation method |
| CN108525648A (en) * | 2018-04-09 | 2018-09-14 | 东华理工大学 | A kind of method of amination magnetism poly phosphazene adsorbent and preparation and separation and enriched uranium |
| CN111171324A (en) * | 2020-01-17 | 2020-05-19 | 北京东方雨虹防水技术股份有限公司 | Load metal type environment-friendly ring crosslinked porous polyphosphazene and preparation method and application thereof |
| CN111659360A (en) * | 2020-07-14 | 2020-09-15 | 中南大学 | Sheet-shaped hexachlorocyclotriphosphazene-p-phenylenediamine polycondensate adsorbing material and preparation method and application thereof |
| CN112973647A (en) * | 2020-12-02 | 2021-06-18 | 广东工业大学 | Polytannic acid-phosphazene coated magnetic 3D polymer micro-nano dye adsorbent and preparation method and application thereof |
| CN115672263A (en) * | 2022-12-02 | 2023-02-03 | 东莞理工学院 | Preparation method of halloysite nanotube composite material and application of halloysite nanotube composite material in uranium pollution treatment |
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Cited By (8)
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| CN108129666A (en) * | 2018-01-15 | 2018-06-08 | 西北工业大学 | Multi-metal oxygen cluster basic ring crosslinked poly-phosphine nitrile hybrid high polymer material and preparation method |
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| CN111171324A (en) * | 2020-01-17 | 2020-05-19 | 北京东方雨虹防水技术股份有限公司 | Load metal type environment-friendly ring crosslinked porous polyphosphazene and preparation method and application thereof |
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| CN112973647A (en) * | 2020-12-02 | 2021-06-18 | 广东工业大学 | Polytannic acid-phosphazene coated magnetic 3D polymer micro-nano dye adsorbent and preparation method and application thereof |
| CN115672263A (en) * | 2022-12-02 | 2023-02-03 | 东莞理工学院 | Preparation method of halloysite nanotube composite material and application of halloysite nanotube composite material in uranium pollution treatment |
| CN115672263B (en) * | 2022-12-02 | 2024-02-13 | 东莞理工学院 | Preparation method of halloysite nanotube composite material and application of halloysite nanotube composite material in uranium pollution treatment |
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