CN103992500B - A kind of Cr (III) ion is combined the preparation method of imprinted polymer adsorbent - Google Patents

A kind of Cr (III) ion is combined the preparation method of imprinted polymer adsorbent Download PDF

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CN103992500B
CN103992500B CN201410191076.7A CN201410191076A CN103992500B CN 103992500 B CN103992500 B CN 103992500B CN 201410191076 A CN201410191076 A CN 201410191076A CN 103992500 B CN103992500 B CN 103992500B
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iii
ion
combined
imprinted polymer
polymer adsorbent
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CN103992500A (en
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王学川
张斐斐
杨月
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Shaanxi University of Science and Technology
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Abstract

The invention discloses a kind of Cr (III) ion and be combined the preparation method of imprinted polymer adsorbent, this adsorbent with Cr (III) ion as template ion, collagen protein and acrylic compounds are bi-functional monomer, in polar solvent, with N, N methylene-bisacrylamide and little molecule cross-linking agents, azodiisobutyronitrile is that initiator causes preparation Cr (III) ion to be combined imprinted polymer adsorbent.Adsorbent prepared by the present invention has the adsorption selectivity of excellence to Cr (III) ion, and soon, elution efficiency is high, renewable recycling for absorption, elution rate.

Description

A kind of Cr (III) ion is combined the preparation method of imprinted polymer adsorbent
Technical field
The invention belongs to technical field of polymer composite materials, be specifically related to the compound print of a kind of Cr (III) ion The preparation method of mark polymer absorbant.
Background technology
In leather industry, in existing tanning agent, account for 70%~80% containing chrome tanning agent, so far, Due to chrome-tanned every premium properties, not yet there is any tanning agent can replace chrome tanning agent completely.Separately On the one hand, in the chrome tanning agent of tanning production, there are about the chromium residues of 1/3rd in chroming waste liquor, Not only waste resource but also environment is caused serious pollution.Due to chromic toxicity, the use of chromic salts is right Environment, people and animals cause high risks.Along with the reinforcement of mankind's environmental consciousness, solve the pollution of leather industry Problem is the most very urgent, especially pollution of chromium.
Molecular imprinting is that one is prepared and had a certain specific molecular (template molecule or microsphere) The process of the new polymers of Selective recognition ability, can be described generally as manufacturing identification " molecule key " Artificial lock technology.Molecular engram is the technology of a kind of advanced person during synthetic polymeric material, to not Same material has artificial receptor, and such as bonding point, in a lot of science and technology field, molecular engram is answered For molecular recognition process, such as Solid-Phase Extraction, chromatographic isolation, membrance separation, induction apparatus, drug release and Catalytic process etc..
As an important development direction of molecular imprinting, the molecular engram skill relevant with metal ion Art, i.e. ionic imprinting technique, with anions and canons as template ion, select and have interaction force with ion (usually electrostatic, be coordinated, the active force such as chelating) function monomer, select suitable cross-linking agent and poly- Conjunction method is polymerized in aqueous, remove just obtain after template ion have special groups arrangement, The ion imprinted polymer of fixed cavitation size and shape.
The engram technology development relevant with metal ion belongs to the forward position content in molecular imprinting, many Research is so far also in the elementary step.In metal ion molecular imprinting, two class contents are had to obtain relatively Many concerns: the metal ion engram technology with metal ion as template;Utilize metal ion and biomolecule Coordination promote, realize the molecular imprinting of biomacromolecule.
Summary of the invention
It is an object of the invention to provide that a kind of adsorption capacity is high, selectivity is good, adsorption and desorption speed is fast, Elution efficiency is high, and Cr (III) ion that regeneration capacity is strong is combined imprinted polymer adsorbent and preparation side thereof Method.
In order to achieve the above object, the technical solution used in the present invention comprises the following steps:
1) collagen protein and function monomer are dissolved in Cr (III) saline solution, are subsequently adding N, N-methylene Base bisacrylamide and initiator, and polyreaction 2-24h at 55 DEG C~60 DEG C, then to the reaction obtained System adds cross-linking agent, reacts 0.5-3.5h at 0 DEG C~50 DEG C, obtain reactant liquor;Wherein, Cr (III) Saline solution is mixed by solubility Cr (III) salt and polar organic solvent, Cr (III) saline solution In Cr (III) ion, the amino in collagen protein, function monomer, N, N-di-2-ethylhexylphosphine oxide acrylamide It is 1:(2~8 with the mol ratio of cross-linking agent): (2~10): (10~40): (0.5~2);
2) solid-liquid separation after being stood by reactant liquor, obtains polymer, by polymer desorbing, is dried, obtains Cr (III) ion is combined imprinted polymer adsorbent;Wherein, the method for desorbing is: by polymer body Long-pending than for (1:7)~the acetic acid of (1:10) and the mixed liquor of methanol and the salt of 0.1mol/L~2.0mol/L Acid is cleaned, and being finally washed till filtrate with distilled water is neutrality.
Described step 1) in function monomer be α-methacrylic acid or acrylamide.
Described step 1) in solubility Cr (III) salt be chromium acetate, chromic sulfate or chromic nitrate.
Described step 1) in polar organic solvent be dimethyl sulfoxide, water, acetone, methanol or N, Dinethylformamide.
Described step 1) in the mass concentration of Cr (III) saline solution be 10%~30%.
Described step 1) in initiator be that dibenzoyl peroxide, dilauroyl peroxide, azo two are different Butyronitrile or persulfate.
Described initiator accounts for collagen protein and the 1.0% of function monomer gross mass~3.0%.
Described cross-linking agent is glutaraldehyde, epoxychloropropane or Biformyl.
Described step 1) in cross-linking agent when being epoxychloropropane, regulate reaction system after adding cross-linking agent To alkalescence.
Described step 1) in polyreaction carry out under nitrogen protection;Step 2) in polymer first It is vacuum dried, grinds, sieves, then take 100~160 purpose polymers and carry out desorbing.
Compared with prior art, the beneficial effects of the present invention is:
The collagen protein that the present invention uses is a kind of typical polyampholyte, its surface contain amino, Carboxyl, hydroxyl isoreactivity functional group, it is possible to form complex with Cr (III), but collagen protein surface Contained active group quantity is limited, and Selective adsorption is the most poor.Therefore, the present invention utilizes ion Blotting synthesizes Cr (III) ion and is combined imprinted polymer adsorbent, and adopting in this way can be notable Increase the precordainment of adsorbent, identity and practicality, improve the adsorbance of chromium in chrome waste liquid, useless In liquid, the clearance of chromium reaches as high as 86.3%.So, Cr (III) ion that the present invention prepares is combined trace and gathers Compound adsorbent is high to Cr in chromate waste water (III) ionic adsorption selectivity, and Cr (III) is had identification Property absorption, the rate of adsorption is big, it is easy to industrialized production, overcome prior art exist adsorbent amount Greatly, halfway problem is adsorbed.
It addition, the Cr that the present invention prepares (III) ion is combined imprinted polymer adsorbent, chromate waste water is changed Having stronger adaptability, stable performance, recyclability is good, it is easy to reclaim, therefore, and Cr of the present invention (III) Ion is combined the production of imprinted polymer adsorbent and use process does not results in secondary pollution to environment, institute Cr (III) ion prepared is combined the absorption property of imprinted polymer adsorbent and is greatly improved.Meanwhile, this The solid waste that bright used collagen protein can produce from leather production process carries as raw material Taking out, therefore, raw material sources of the present invention are extensive, and nontoxic, with low cost.
Detailed description of the invention
Embodiment 1:
1) chromic nitrate is dissolved in dimethyl sulfoxide make mass concentration is 28% Cr (III) saline solution, It is subsequently adding collagen protein and α-methacrylic acid, stirs 2h under room temperature and make uniformly, to add N, N- Methylene-bisacrylamide and azodiisobutyronitrile are also passed through nitrogen 30min, seal, in the constant temperature of 60 DEG C Water-bath is reacted 24h, in the reaction system obtained, then adds glutaraldehyde, protect in sealed environment and nitrogen Protect down and react 3h in 30 DEG C, obtain reactant liquor;Wherein, Cr (III) in Cr (III) saline solution added Amino in ion, collagen protein, α-methacrylic acid, N, N-di-2-ethylhexylphosphine oxide acrylamide, glutaraldehyde Mol ratio is 1:2:4:20:0.5;The quality of the azodiisobutyronitrile added accounts for collagen protein and α-first The 1.0% of base acrylic acid gross mass;
2) solid-liquid separation after being stood by reactant liquor, obtains polymer;By polymer in 60 DEG C of vacuum drying, Then mill, sieve, take 100~160 purpose polymers and carry out desorbing, then in 60 DEG C in vacuum drying oven Dry, i.e. obtain Cr (III) ion and be combined imprinted polymer adsorbent;Wherein, desorbing method particularly includes: By 100~160 purpose polymers successively with the acetic acid that volume ratio is 1:9 and the mixed liquor of methanol, 1.0mol/L Hydrochloric acid cyclic washing, being finally washed till filtrate with distilled water is neutrality.
Embodiment 2:
1) chromic nitrate is dissolved in methanol makes Cr (III) saline solution that mass concentration is 28%, then add Enter collagen protein and α-methacrylic acid, stir 2h under room temperature and make uniformly, add N, N-di-2-ethylhexylphosphine oxide Acrylamide and azodiisobutyronitrile are also passed through nitrogen 30min, seal, anti-in the water bath with thermostatic control of 60 DEG C Answer 24h, in the reaction system obtained, then add glutaraldehyde, 30 DEG C of reaction 3.5h, obtain reactant liquor; Wherein, the amino in Cr (III) ion, collagen protein, α-first in Cr (III) saline solution added Base acrylic acid, N, N-di-2-ethylhexylphosphine oxide acrylamide, the mol ratio of glutaraldehyde are 1:4:8:10:0.8;Added The quality of the azodiisobutyronitrile entered accounts for collagen protein and the 3% of α-methacrylic acid gross mass;
2) solid-liquid separation after being stood by reactant liquor, obtains polymer;Polymer is vacuum dried at 60 DEG C, Then mill, sieve, take 100~160 purpose polymers and carry out desorbing, then in 60 DEG C in vacuum drying oven Dry, i.e. obtain Cr (III) ion and be combined imprinted polymer adsorbent;Wherein, desorbing method particularly includes: By acetic acid that 100~160 purpose polymers volume ratios are 1:9 and the mixed liquor of methanol, the salt of 0.5mol/L Acid cyclic washing, being finally washed till filtrate with distilled water is neutrality.
Embodiment 3:
1) chromic sulfate is dissolved in dimethyl sulfoxide make mass concentration is 30% Cr (III) saline solution, The collagen protein being subsequently adding and α-methacrylic acid, stir 2h and make uniformly, to add N under room temperature, N-methylene-bisacrylamide and azodiisobutyronitrile are also passed through nitrogen 30min, seal, in the perseverance of 60 DEG C Tepidarium is reacted 24h, in the reaction system obtained, then adds epoxychloropropane, and regulate pH value It is 10, at 50 DEG C, reacts 3.5h, obtain reactant liquor;Wherein, in Cr (III) saline solution added Amino in Cr (III) ion, collagen protein, α-methacrylic acid, N, N-di-2-ethylhexylphosphine oxide acrylamide, The mol ratio of epoxychloropropane is 1:4:10:20:0.8;The quality of the azodiisobutyronitrile added accounts for glue Former albumen and the 2.5% of α-methacrylic acid gross mass;
2) solid-liquid separation after being stood by reactant liquor, obtains polymer;Polymer is vacuum dried at 60 DEG C, Then mill, sieve, take 100~160 purpose polymers and carry out desorbing, then in 60 DEG C in vacuum drying oven Dry, i.e. obtain Cr (III) ion and be combined imprinted polymer adsorbent;Wherein, desorbing method particularly includes: By 100~160 purpose polymers successively with the acetic acid that volume ratio is 1:10 and the mixed liquor 1.0mol/L of methanol Hydrochloric acid cyclic washing, being finally washed till filtrate with distilled water is neutrality.
Embodiment 4:
1) chromium acetate is dissolved in methanol make mass concentration is 15% Cr (III) saline solution, then Add collagen protein and acrylamide, stir 2h under room temperature and make uniformly, add N, N-di-2-ethylhexylphosphine oxide third Acrylamide and azodiisobutyronitrile are also passed through nitrogen 30min, seal, and react in the water bath with thermostatic control of 60 DEG C 24h, then adds glutaraldehyde, in 50 DEG C under sealed environment and nitrogen are protected in the reaction system obtained Reaction 3.5h, obtains reactant liquor;Cr (III) ion in Cr (III) saline solution wherein, added, Amino in collagen protein, acrylamide, N, N-di-2-ethylhexylphosphine oxide acrylamide, the mol ratio of glutaraldehyde are 1: 2:10:20:1.0;The quality of the azodiisobutyronitrile added accounts for collagen protein and acrylamide gross mass 2%;
2) solid-liquid separation after being stood by reactant liquor, obtains polymer;Polymer is vacuum dried at 60 DEG C, Then mill, sieve, take 100~160 purpose polymers and carry out desorbing, then in 60 DEG C in vacuum drying oven Vacuum drying oven is dried, i.e. obtains Cr (III) ion and be combined imprinted polymer adsorbent;Wherein, desorbing Method particularly includes: by 100~160 purpose polymers successively with the acetic acid that volume ratio is 1:10 and methanol The hydrochloric acid cyclic washing of mixed liquor 1.0mol/L, being finally washed till filtrate with distilled water is neutrality.
Embodiment 5:
1) by soluble in water for chromium acetate make mass concentration is 10% Cr (III) saline solution, then add Enter collagen protein and acrylamide, stir 2h under room temperature and make uniformly, add N, N-methylene bisacrylamide Amide and dibenzoyl peroxide are also passed through nitrogen 30min, seal, and react in the water bath with thermostatic control of 55 DEG C 2h, then adds Biformyl in the reaction system obtained, anti-in 0 DEG C under sealed environment and nitrogen are protected Answer 2.0h, obtain reactant liquor;Wherein, Cr (III) ion, glue in Cr (III) saline solution added Amino in former albumen, acrylamide, N, N-di-2-ethylhexylphosphine oxide acrylamide, the mol ratio of Biformyl are 1:8: 2:40:2.0;The quality of the dibenzoyl peroxide added accounts for collagen protein and acrylamide gross mass 1.0%;
2) solid-liquid separation after being stood by reactant liquor, obtains polymer;Polymer is vacuum dried at 60 DEG C, Then mill, sieve, take 100~160 purpose polymers and carry out desorbing, then in 60 DEG C in vacuum drying oven Vacuum drying oven is dried, i.e. obtains Cr (III) ion and be combined imprinted polymer adsorbent;Wherein, desorbing Method particularly includes: mixed with the acetic acid that volume ratio is 1:7 and methanol successively by 100~160 purpose polymers Closing the hydrochloric acid cyclic washing of liquid 2.0mol/L, being finally washed till filtrate with distilled water is neutrality.
Embodiment 6:
1) chromic sulfate is dissolved in DMF make mass concentration is 20% Cr (III) Saline solution, the collagen protein being subsequently adding and α-methacrylic acid, stir 2h and make uniformly, then add under room temperature Enter N,N methylene bis acrylamide and dilauroyl peroxide and be passed through nitrogen 30min, sealing, in 57 DEG C Water bath with thermostatic control in react 16h, in the reaction system obtained, then add epoxychloropropane, and regulate PH value is 10, reacts 0.5h, obtain reactant liquor at 20 DEG C;Wherein, Cr (III) salt added is molten Amino in Cr (III) ion, collagen protein, α-methacrylic acid, N, N-methylene diene acyl in liquid Amine, the mol ratio of epoxychloropropane are 1:4:10:30:0.8;The quality of the dilauroyl peroxide added Account for collagen protein and the 1.0% of α-methacrylic acid gross mass;
2) solid-liquid separation after being stood by reactant liquor, obtains polymer;Polymer is vacuum dried at 60 DEG C, Then mill, sieve, take 100~160 purpose polymers and carry out desorbing, then in 60 DEG C in vacuum drying oven Dry, i.e. obtain Cr (III) ion and be combined imprinted polymer adsorbent;Wherein, desorbing method particularly includes: By 100~160 purpose polymers successively with the acetic acid that volume ratio is 1:8 and the mixed liquor 1.0mol/L of methanol Hydrochloric acid cyclic washing, being finally washed till filtrate with distilled water is neutrality.
Embodiment 7:
1) chromic nitrate is dissolved in acetone makes Cr (III) saline solution that mass concentration is 15%, then add Enter collagen protein and α-methacrylic acid, stir 2h under room temperature and make uniformly, add N, N-di-2-ethylhexylphosphine oxide Acrylamide and persulfate are also passed through nitrogen 30min, seal, and react 7h in the water bath with thermostatic control of 60 DEG C, Then in the reaction system obtained, add glutaraldehyde, 30 DEG C of reaction 3.5h, obtain reactant liquor;Wherein, Amino in Cr (III) ion, collagen protein, Alpha-Methyl propylene in Cr (III) saline solution added Acid, N, N-di-2-ethylhexylphosphine oxide acrylamide, the mol ratio of glutaraldehyde are 1:4:8:10:0.8;The mistake added The quality of sulfate accounts for collagen protein and the 3% of α-methacrylic acid gross mass;
2) solid-liquid separation after being stood by reactant liquor, obtains polymer;Polymer is vacuum dried at 60 DEG C, Then mill, sieve, take 100~160 purpose polymers and carry out desorbing, then in 60 DEG C in vacuum drying oven Dry, i.e. obtain Cr (III) ion and be combined imprinted polymer adsorbent;Wherein, desorbing method particularly includes: By acetic acid that 100~160 purpose polymers volume ratios are 1:9 and the mixed liquor of methanol, the salt of 0.5mol/L Acid cyclic washing, being finally washed till filtrate with distilled water is neutrality.
Persulfate in embodiment 7 can be Ammonium persulfate., potassium peroxydisulfate or sodium peroxydisulfate.

Claims (8)

1. Cr (III) ion is combined the preparation method of imprinted polymer adsorbent, it is characterised in that Comprise the following steps:
1) collagen protein and function monomer are dissolved in Cr (III) saline solution, are subsequently adding N, N-methylene Base bisacrylamide and initiator, and polyreaction 2-24h at 55 DEG C~60 DEG C, then to the reaction obtained System adds cross-linking agent, reacts 0.5-3.5h at 0 DEG C~50 DEG C, obtain reactant liquor;Wherein, Cr (III) Saline solution is mixed by solubility Cr (III) salt and polar organic solvent, Cr (III) saline solution In Cr (III) ion, the amino in collagen protein, function monomer, N, N-di-2-ethylhexylphosphine oxide acrylamide It is 1:(2~8 with the mol ratio of cross-linking agent): (2~10): (10~40): (0.5~2);Described step 1) In function monomer be α-methacrylic acid or acrylamide;Described cross-linking agent is glutaraldehyde, epoxy chlorine Propane or Biformyl;
2) solid-liquid separation after being stood by reactant liquor, obtains polymer, by polymer desorbing, is dried, obtains Cr (III) ion is combined imprinted polymer adsorbent;Wherein, the method for desorbing is: by polymer body Long-pending than for (1:7)~the acetic acid of (1:10) and the mixed liquor of methanol and the salt of 0.1mol/L~2.0mol/L Acid is cleaned, and being finally washed till filtrate with distilled water is neutrality.
Cr the most according to claim 1 (III) ion is combined the preparation side of imprinted polymer adsorbent Method, it is characterised in that: described step 1) in solubility Cr (III) salt be chromium acetate, chromic sulfate Or chromic nitrate.
Cr the most according to claim 1 (III) ion is combined the preparation side of imprinted polymer adsorbent Method, it is characterised in that: described step 1) in polar organic solvent be dimethyl sulfoxide, acetone, first Alcohol or DMF.
4. it is combined imprinted polymer adsorbent according to Cr (III) ion described in claim 1,2 or 3 Preparation method, it is characterised in that: described step 1) in the mass concentration of Cr (III) saline solution be 10%~30%.
Cr the most according to claim 1 (III) ion is combined the preparation side of imprinted polymer adsorbent Method, it is characterised in that: described step 1) in initiator be dibenzoyl peroxide, peroxidating 12 Acyl, azodiisobutyronitrile or persulfate.
Cr the most according to claim 5 (III) ion is combined the preparation side of imprinted polymer adsorbent Method, it is characterised in that: described initiator accounts for collagen protein and the 1.0% of function monomer gross mass~3.0%.
Cr the most according to claim 1 (III) ion is combined the preparation side of imprinted polymer adsorbent Method, it is characterised in that: described step 1) in cross-linking agent when being epoxychloropropane, after adding cross-linking agent Regulation reaction system is to alkalescence.
Cr the most according to claim 1 (III) ion is combined the preparation side of imprinted polymer adsorbent Method, it is characterised in that: described step 1) in polyreaction carry out under nitrogen protection;Step 2) Middle polymer is first vacuum dried, grinds, sieves, and then takes 100~160 purpose polymers and carries out desorbing.
CN201410191076.7A 2014-05-07 2014-05-07 A kind of Cr (III) ion is combined the preparation method of imprinted polymer adsorbent Expired - Fee Related CN103992500B (en)

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CN105148851B (en) * 2015-09-28 2018-10-19 太原理工大学 A kind of Preparation method and use of urea groups functionalization cadmium ion surface imprint adsorbent
CN105949389B (en) * 2016-05-12 2018-01-12 广东省稀有金属研究所 A kind of preparation method of germanium ion imprinted polymer
CN110339729A (en) * 2019-07-02 2019-10-18 昆明理工大学 A kind of preparation method and application of trivalent chromic ion trace composite membrane
CN112898455B (en) * 2021-01-25 2022-12-09 徐州工程学院 Chromium (VI) molecular imprinting material and preparation method and application thereof
CN115069223B (en) * 2022-06-30 2023-10-27 陕西科技大学 Chitosan ion imprinting gel for adsorbing Cd (II) as well as preparation method and application thereof

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