CN109851717A - A kind of preparation method and application of anionic PSSS/PSA microballoon - Google Patents
A kind of preparation method and application of anionic PSSS/PSA microballoon Download PDFInfo
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- CN109851717A CN109851717A CN201910057694.5A CN201910057694A CN109851717A CN 109851717 A CN109851717 A CN 109851717A CN 201910057694 A CN201910057694 A CN 201910057694A CN 109851717 A CN109851717 A CN 109851717A
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Abstract
The invention discloses a kind of preparation method and applications of anionic PSSS/PSA microballoon, belong to functional polymer material field.The present invention passes through radical polymerization, sodium p styrene sulfonate (SSS) is graft-polymerized in polystyrene primary amine microsphere surface in solution polymerization system, it is prepared for the composite particles that surface grafting has SSS, it is grafted particle PSSS/PSA, and it is used for absorption Pidolidone, theoretical reference is provided to prepare new function composite particles.
Description
Technical field
The present invention relates to a kind of preparation method and applications of anionic PSSS/PSA microballoon, belong to functional polymer material
Field.
Background technique
Pidolidone is the maximum amino acid of yield in the world at present, it be both protein or peptide structural amino acid it
One, and be free amino acid.Pidolidone both can be used as the metabolism that functional leaves participate in body, there is higher nutritive value；
It is the main composition of protein again, while has extensively in food, medicine, artificial process hides, cosmetics industry and industrial or agricultural
General purposes.The separation method of paddy amino acid has chemical resolution method, crystallisation, enzyme process, chromatography and partition method, and (including chirality is matched
The methods such as base exchange chromatography, high performance liquid chromatography, gas-chromatography and capillary electrophoresis) the applicable range of these types separation method
Narrow and process is complicated;And some chromatographies, although selective good and separative efficiency is high, (especially chiral ligands exchange color
Spectrometry), but it is all confined to analytical chemistry field, it still can not achieve quick, efficient, scale separation.Therefore, it is chiral right to realize
The efficient separating of body is reflected, this is an extremely challenging problem.
Summary of the invention
The present invention is intended to provide a kind of preparation method and application of anionic PSSS/PSA microballoon, the present invention pass through freedom
Sodium p styrene sulfonate (SSS) is graft-polymerized in polystyrene primary amine microsphere surface in solution polymerization system by base polymerization,
The composite particles that surface grafting has SSS are prepared for, i.e. grafting particle PSSS/PSA, and are used for absorption Pidolidone, for system
Standby new function composite particles provide theoretical reference.
In the present invention, primary amine resin has after being grafted again with sodium p styrene sulfonate (SSS) after being modified
Sulfonic acid functional group.In adsorption process, due in glutamic acid amino and carboxyl oxygen atom can deposit with the oxygen atom in sulfonate radical
In hydrogen bonding interaction, therefore the binding site with specific binding performance can be formed.Preparation process and absorption principle
It is as follows:
The present invention provides a kind of preparation methods of anionic PSSS/PSA microballoon, poly- in solution by radical polymerization
Sodium p styrene sulfonate (SSS) is graft-polymerized in polystyrene primary amine microsphere surface in zoarium system, being prepared for surface grafting has
The composite particles of SSS, i.e. grafting particle PSSS/PSA, specifically includes the following steps:
(1) activation processing of polystyrene primary amine resin microballoon:
50mL-100mLN, dinethylformamide solution, at 20-30 DEG C is added in 20g-40g dry primary amine resin microballoon
At a temperature of impregnate 12-14 hours after filter, be put into vacuum drying oven and be dried, can be by primary amine resin microsphere surface ammonia
Base activation；
(2) in primary amine resin microsphere surface graft polymerization sodium p styrene sulfonate:
The 0.1g-0.3g primary amine resin microballoon activated is added in four-hole boiling flask, and 40mL-45mL solvent, 0.2500- is added
0.3500gSSS, logical nitrogen 20-40min start to be heated up with water-bath agitating and heating, and 0.04- is added after temperature reaches 50 DEG C
0.08g initiator ammonium persulfate starts to react；6-10h uses the repeated multiple times washing of distilled water after reaction, then with distillation water logging
It is filtered after bubble 22-26h, 22-26h then is dried at 40-60 DEG C with vacuum drying oven, grafting particle PSSS/PSA is made.
Above-mentioned preparation method, in step (2), the solvent is the mixed solvent of first alcohol and water, and the volume ratio of the two is
5:1-5:3。
Above-mentioned preparation method in step (2), when with distilled water immersion, replaces 40-50mL distilled water every 4-6h.
In above-mentioned preparation method, the dosage of SSS is the 0.4-0.8% of all total mass of raw materiales；Initiator ammonium persulfate
Dosage is the 20-22% of monomer mass.
Above-mentioned preparation method, specifically includes the following steps:
(1) activation processing of polystyrene primary amine resin microballoon
100mLN, dinethylformamide solution, after impregnating 12h at room temperature are added in 30g dry primary amine resin microballoon
It filters, is put into vacuum drying oven and is dried, i.e., activate resin microsphere surface amino groups；
(2) in primary amine resin microsphere surface graft polymerization sodium p styrene sulfonate
The 0.2g primary amine resin microballoon activated is added in the four-hole boiling flask of 100mL, and 42mL solvent is added,
0.2887gSSS, logical nitrogen 30min start to be heated up with water-bath agitating and heating, and 0.0600g is added after temperature reaches 50 DEG C and draws
Hair agent ammonium persulfate starts to react；8h uses the repeated multiple times washing of distilled water after reaction, then is taken out afterwards for 24 hours with distilled water immersion
Then filter is dried at 50 DEG C for 24 hours with vacuum drying oven, grafting particle PSSS/PSA is made；
The solvent is the mixed solvent of first alcohol and water, and the volume ratio of the two is 5:2.
The present invention provides anionic PSSS/PSA microballoons made from above-mentioned preparation method.
The present invention provides application of the above-mentioned anionic PSSS/PSA microballoon in absorption Pidolidone.
In above-mentioned application, the Pidolidone standard solution of 0.1-1.0mol/L is prepared with volumetric flask, then measures 10-
The Pidolidone standard solution of 20mL is placed in conical flask, and anionic PSSS/PSA microballoon is added as adsorbent material, will bore
Shape bottle is placed in constant temperature oscillation case, is adsorbed at 20-50 DEG C；Suitable time gradient is set, is taken out every 10-30min
Conical flask stands centrifuging and taking supernatant, surveys its UV absorption intensity.
Beneficial effects of the present invention:
The relatively large functional material of grafting amount can be made by the investigation to influence factor each in preparation process in the present invention.
Since this material has a large amount of sulfonic acid groups, the oxygen in sulfonic acid group can be with the ammonia nitrogen and carboxyl oxygen meeting shape on L-Glu
At hydrogen bond, so this material can largely adsorb L-Glu, adsorbance is up to 110 ~ 130mg/g.
Detailed description of the invention
Fig. 1 is the infrared spectrogram of PSA/PSSS/PSA and MIP-PSSS/PSA in embodiment 1；
Fig. 2 is influence of the solvent to graft polymerization in embodiment 2；
Fig. 3 is influence of the initiator to graft polymerization in embodiment 3；
Fig. 4 is influence of the monomer dosage to grafting degree in embodiment 4；
Fig. 5 is influence of the reaction time to grafting degree in embodiment 5；
Fig. 6 is influence of the reaction temperature to grafting degree in embodiment 6；
Fig. 7 is PSSS/PSA under condition of different pH to glutamic acid absorption isotherm；
Fig. 8 is PSSS/PSA under different temperatures to the absorption isotherm of glutamic acid；
Fig. 9 is the repeat performance effect picture for being grafted microballoon PSSS/PSA.
Specific embodiment
The present invention is further illustrated below by embodiment, but is not limited to following embodiment.
The preparation and application of embodiment 1:PSSS/PSA
Preparation process specifically includes the following steps:
(1) activation processing of polystyrene primary amine resin microballoon:
The n,N-Dimethylformamide solution of 100mL is added in the primary amine resin microballoon of the drying of 30g, in 20-30 DEG C of temperature
It is filtered after lower immersion 12h, is put into vacuum drying oven and is dried, it can be by primary amine resin microsphere surface amino-reactive；
(2) in primary amine resin microsphere surface graft polymerization sodium p styrene sulfonate:
The 0.2g primary amine resin microballoon activated is added in four-hole boiling flask, and 42mL solvent (V is addedMethanol: VWater=5:2),
0.2887g (the 0.6235% of gross mass) SSS, logical nitrogen 30min starts to be heated up with water-bath agitating and heating, when temperature reaches 50
0.0600g initiator ammonium persulfate (the 20.78% of monomer mass) is added after DEG C to start to react；8h uses distilled water after reaction
Repeated multiple times washing, then (constantly change water) for 24 hours with distilled water immersion and filter afterwards, it is then dried with vacuum drying oven, temperature is
50 DEG C, for 24 hours, grafting particle PSSS/PSA is made in drying.
With the salt acid soak PSSS/PSA 8h of certain volume, react hydrochloric acid sufficiently with the amino of primary amine resin ball surface
Afterwards, it then is gone to titrate remaining hydrochloric acid with the NaOH of standard, the grafting degree of PSSS/PSA is calculated by formula.It can be made under the program
Grafting amount is 120mg/g.
Function grafting particle PSSS/PSA is used for the absorption to glutamic acid below
The Pidolidone standard solution of 0.25mg/g is prepared with volumetric flask, the Pidolidone standard solution for then measuring 20mL is placed in
In several conical flasks, grafting particle is separately added into as adsorbent material, conical flask is placed in constant temperature oscillation case, in certain temperature
It is adsorbed under degree.
The present embodiment characterizes above-mentioned products obtained therefrom: if Fig. 1 is three kinds of particles (PSA, PSSS/PSA and MIP-
PSSS/PSA infrared spectrogram), as can be seen that 1650cm from spectrogram-1There is the characteristic absorption peak of double bond at place, illustrates substrate not
Energy fully reacting, 3400cm-1Place is NH2Stretching vibration peak, 3750cm-1It is the stretching vibration peak of N-H, 1678cm-1Place is acyl
The stretching vibration absworption peak of amine carbonyl, 1576cm-1Place is that the in-plane bending of amide N-H absorbs vibration peak, the two peaks are selfed
The MBA to ally the communists in polymers；1460cm-1And 1410cm-1Place is respectively the characteristic absorption peak of methylene and methine, illustrates primary amine
Double bond in ball and monomer SSS has occurred polyaddition reaction, and 1190cm-1There is sulfonic group-SO at place3-Characteristic absorption peak it is bright
It is aobvious to reinforce, illustrate that monomer has successfully been grafted to primary amine microsphere surface.
Embodiment 2: influence of the solvent burden ratio to graft polymerization of the present invention
The technique of the present embodiment is same as Example 1, change polymerization process in solvent type and dosage, carried out five groups it is parallel
Experiment: the 1. mixed solvent of methanol and water: VMethanol:VWater=1:1；2. the mixed solvent of ethyl alcohol and water: VEthyl alcohol:VWater=1:1；3. methanol with
The mixed solvent of water: VMethanol:VWater=5:2；4. solvent is water, 5. solvent is methanol.
It is obtained from Fig. 2 result, solvent VMethanol:VWaterWhen=5:2, grafting degree is maximum, and reason may be in inorganic solvent water
In sulfonic degree of ionization it is smaller, and its hydrogen bond action is smaller in other organic solvent ethyl alcohol, but sodium p styrene sulfonate
It is insoluble in methanol, therefore water is added to increase its dissolubility, is then determined by experiment the ratio of methanol and water, last VMethanol: VWater=5:2 is
Optimum solvent.
Embodiment 3: influence of the initiator amount to graft polymerization of the present invention
The technique of the present embodiment is same as Example 1, changes the initiator amount in polymerization process, has carried out parallel laboratory test.
If Fig. 3 is shown, be graft-polymerized with the increase of initiator ammonium persulfate quality first increases and then decreases, works as ammonium persulfate
Be the 5.73% of 0.06g(monomer mass) when grafting degree maximum reason may be: 1) PSSS being grafted to early period on primary amine microballoon
Macromolecular chain, which is mutually wound, to be overlapped, and the fine and close polymer barrier layer (work of dynamical fusion barrier can be formed in primary amine microsphere surface
With), it hinders the diffusion of monomer SSS and makes the slack-off of rate of polymerization when the mass fraction of persulfate is more than 5.73%, polymerization speed
Rate is too fast, will form fine and close barrier layer in primary amine ball surface in the short time and the graft polymerization of SSS is caused to be obstructed, make to be grafted
Rate is slack-off, and grafting degree becomes smaller.2) amount of initiator, which crosses conference, makes the homopolymerization rate between monomer SSS accelerate and make monomer
The graft polymerization rate of SSS and primary amine microballoon are slack-off.The optimum evocating agent amount that graft polymerization is obtained by experiment is 0.0600g (single
The 5.73% of weight).
Embodiment 4: influence of the monomer dosage to graft polymerization of the present invention
The technique of the present embodiment is same as Example 1, changes the monomer dosage in polymerization process, has carried out parallel laboratory test.
As shown in figure 4, grafting degree is first with the increase of the mass fraction of monomer in solution in the case where other conditions are certain
It is slowly increased, reaction is reduced rapidly again after reaching maximum to a certain extent, when the mass fraction of SSS is 2.22%(solution quality
Percentage) when, grafting degree maximum (230.27mg/g) the reason is that with monomer mass increase (concentration of substrate becomes larger), body
The amino number activated in system is certain, can rapidly accelerate with monomer reaction, graft polymerization rate, grafting degree becomes larger, but works as SSS
When mass fraction increases to 2.22%, because graft polymerization reaction causes the amino in primary amine resin fewer and fewer very much fastly, it polymerize simultaneously
Object forms fine and close barrier layer on primary amine resin surface, keeps reaction rate slack-off, grafting degree becomes smaller.Graft polymerization is obtained by experiment
Best amount of monomer be 1.0464g (the 2.22% of solution quality percentage).
Embodiment 5: influence of the reaction time to graft polymerization of the present invention
The technique of the present embodiment is same as Example 1, changes the reaction time in polymerization process, has carried out parallel laboratory test.
As shown in figure 5, show that grafting degree increases with the extension of time first in the case where other conditions are certain,
When reaching 8h between when reacted, the grafting degree of grafting particle PSSS/PSA reaches maximum.Later as the increase in reaction time connects
Branch degree reduces instead, reason may be (1) time it is too short when reaction without carry out completely, there are also remaining substrate it is not anti-
It answers, grafting degree is caused to become smaller.Main chain when overlong time in reactive grafting starts to degrade again, so that grafting degree declines, so
The Best Times that this experiment is graft-polymerized are 8h.
Embodiment 6: influence of the reaction temperature to graft polymerization of the present invention
The technique of the present embodiment is same as Example 1, changes the reaction temperature in polymerization process, has carried out parallel laboratory test.
If Fig. 6 is shown, it is grafted the grafting degree of microballoon with the raising first increases and then decreases of temperature, at 50 DEG C, maximum grafting
It spends up to 230.27mg/g.When the temperature is low, it is slower to cause step, the free radical quantity of polystyrene primary amine microsphere surface compared with
It is few, thus grafting degree is low；The speed for causing step is accelerated as the temperature rises, and primary amine ball surface free radical quantity also increases
More, the quickening of graft polymerization reaction speed increases grafting degree.Two reactions vied each other can occur for the ammonium persulfate in system
(initiation reaction, pyrolysis), after temperature is more than 50 DEG C, rhermal decomposition rate is accelerated and makes the over cure for participating in initiation reaction
Sour ammonium molecular number is reduced, and keeps grafting rate slack-off, so the grafting degree for being grafted ball after temperature is more than 50 DEG C increases instead with temperature
And it reduces.The optimum temperature that graft polymerization is obtained by experiment is 50 DEG C.
Influence of the embodiment 7:pH value to grafting particle PSSS/PSA to glutamate molecule absorption property
The grafting particle PSSS/PSA of 0.02g is weighed respectively in the conical flask of 5 50ml, is posted label and is denoted as No. 1, No. 2,3
Number, No. 4, No. 5, then take 5 conical flask mark originals 1, original 2, original 3, original 4, original 5, be then respectively added in 5 100mL volumetric flasks
The Pidolidone solution 3mL of 1g/L through preparing is settled to scale with the aqueous solvent that pH is 2,4,5,7,9 respectively, corresponding
It is separately added into 20mL solution in conical flask, seals, constant temperature oscillation at 22 DEG C carries out adsorption reaction.All taken out after 1h, stand from
The heart surveys UV absorption intensity, calculates corresponding concentration and adsorbance, investigates PH and adsorbs glutamic acid to grafting microballoon PSSS/PSA
The influence of generation.
Show that grafting particle PSSS/PSA increases the equilibrium adsorption of Pidolidone with the increase of pH by Fig. 7, when pH=4
When, adsorbance reaches maximum, and adsorbance reduces with the increase of pH again later.This is because being grafted particle when pH is less than 4
Hydrogen bond action is smaller between PSSS/PSA and Pidolidone.When pH increases, and is greater than 4, the degree of ionization of sulfonic acid increases, with sulfonate radical
In the presence of hydrogen bond action becomes fainter, and suction-operated becomes smaller, and equilibrium adsorption capacity is caused to become smaller.So optimal adsorption pH is 4.
Embodiment 8: influence of the different temperatures to grafting particle PSSS/PSA to glutamate molecule absorption property
The present embodiment is identical with the application process of embodiment 7, changes different adsorption temps, investigates temperature to grafting particle
Influence of the PSSS/PSA to glutamate molecule absorption property.Temperature settings are as follows: 30 DEG C, 35 DEG C, 40 DEG C, 45 DEG C.
PSSS/PSA is as shown in Figure 8 to the absorption isotherm of stevioside sweet solution under different temperatures.It is grafted particle PSSS/
PSA reduces the adsorption capacity of glutamic acid aqueous solution with the raising of system temperature.As previously mentioned, driving particle PSSS/PSA
Hydrogen bond force between host-guest is mostly come to the active force of glutamic acid aqueous solution absorption.This absorption is generally heat release
Journey, as temperature gradually rises, this suction-operated all can obviously weaken so as to cause adsorbance reduction.The result shows that 30
DEG C when PSSS/PSA and glutamic acid aqueous solution molecule between active force it is most strong, adsorbance is maximum.
Embodiment 9: the repeat performance of grafting microballoon PSSS/PSA
Fig. 9 is grafting particle PSSS/PSA in the effect after 4 uses.
Grafting particle PSSS/PSA is obtained after 4 elutions by Fig. 9, adsorbance 111.6mg/g has good
Reusability, effective percentage be 93%.
Claims (8)
1. a kind of preparation method of anionic PSSS/PSA microballoon, it is characterised in that: poly- in solution by radical polymerization
Sodium p styrene sulfonate SSS is graft-polymerized in polystyrene primary amine microsphere surface in zoarium system, being prepared for surface grafting has SSS
Composite particles, i.e., grafting particle PSSS/PSA, specifically includes the following steps:
(1) activation processing of polystyrene primary amine resin microballoon:
50mL-100mLN, dinethylformamide solution, at 20-30 DEG C is added in 20g-40g dry primary amine resin microballoon
At a temperature of impregnate 12-14 hours after filter, be put into vacuum drying oven and be dried, can be by primary amine resin microsphere surface ammonia
Base activation；
(2) in primary amine resin microsphere surface graft polymerization sodium p styrene sulfonate:
The 0.1g-0.3g primary amine resin microballoon activated is added in four-hole boiling flask, and 40mL-45mL solvent, 0.2500- is added
0.3500gSSS, logical nitrogen 20-40min start to be heated up with water-bath agitating and heating, and 0.04- is added after temperature reaches 50 DEG C
0.08g initiator ammonium persulfate starts to react；6-10h uses the repeated multiple times washing of distilled water after reaction, then with distillation water logging
It is filtered after bubble 22-26h, 22-26h then is dried at 40-60 DEG C of vacuum drying oven, grafting particle PSSS/PSA is made.
2. the preparation method of anionic PSSS/PSA microballoon according to claim 1, it is characterised in that: in step (2),
The solvent is the mixed solvent of first alcohol and water, and the volume ratio of the two is 5:1-5:3.
3. the preparation method of anionic PSSS/PSA microballoon according to claim 1, it is characterised in that: in step (2),
When with distilled water immersion, 40-50mL distilled water is replaced every 4-6h.
4. the preparation method of anionic PSSS/PSA microballoon according to claim 1, it is characterised in that: the dosage of SSS
For the 0.4-0.8% of total mass of raw material；The dosage of initiator ammonium persulfate is the 20-22% of monomer mass.
5. the preparation method of anionic PSSS/PSA microballoon according to claim 1, it is characterised in that including following step
It is rapid:
(1) activation processing of polystyrene primary amine resin microballoon
100mLN, dinethylformamide solution, after impregnating 12h at room temperature are added in 30g dry primary amine resin microballoon
It filters, is put into vacuum drying oven and is dried, i.e., activate resin microsphere surface amino groups；
(2) in primary amine resin microsphere surface graft polymerization sodium p styrene sulfonate
The 0.2g primary amine resin microballoon activated is added in the four-hole boiling flask of 100mL, and 42mL solvent is added,
0.2887gSSS, logical nitrogen 30min start to be heated up with water-bath agitating and heating, and 0.0600g is added after temperature reaches 50 DEG C and draws
Hair agent ammonium persulfate starts to react；8h uses the repeated multiple times washing of distilled water after reaction, then is taken out afterwards for 24 hours with distilled water immersion
Then filter is dried at 50 DEG C for 24 hours with vacuum drying oven, grafting particle PSSS/PSA is made；
The solvent is the mixed solvent of first alcohol and water, and the volume ratio of the two is 5:2.
6. anionic PSSS/PSA microballoon made from a kind of described in any item preparation methods of claim 1 ~ 5.
7. a kind of application of anionic PSSS/PSA microballoon as claimed in claim 6 in absorption Pidolidone.
8. application according to claim 7, it is characterised in that: prepare the Pidolidone mark of 0.1-1.0mol/L with volumetric flask
Quasi- solution, the Pidolidone standard solution for then measuring 10-20mL are placed in conical flask, and anionic PSSS/PSA microballoon is added
As adsorbent material, conical flask is placed in constant temperature oscillation case, is adsorbed at 20-50 DEG C；Suitable time ladder is set
Degree takes out conical flask every 10-30min, stands centrifuging and taking supernatant, survey its UV absorption intensity.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111841513A (en) * | 2020-07-22 | 2020-10-30 | 中北大学 | Preparation method and application of functional microspheres capable of efficiently adsorbing cationic dye |
| CN113797899A (en) * | 2021-09-06 | 2021-12-17 | 肇庆医学高等专科学校 | Preparation method of P (Allyl-beta-CD)/PSA microspheres and application of P (Allyl-beta-CD)/PSA microspheres in adsorption of cinchonine |
-
2019
- 2019-01-22 CN CN201910057694.5A patent/CN109851717A/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| 余佳照等: "阴离子型PSSS/PSA微球的制备及对谷氨酸的吸附性能初探", 《精细化工中间体》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111841513A (en) * | 2020-07-22 | 2020-10-30 | 中北大学 | Preparation method and application of functional microspheres capable of efficiently adsorbing cationic dye |
| CN111841513B (en) * | 2020-07-22 | 2023-03-14 | 山西铁居环保科技有限公司 | Preparation method and application of functional microspheres capable of efficiently adsorbing cationic dye |
| CN113797899A (en) * | 2021-09-06 | 2021-12-17 | 肇庆医学高等专科学校 | Preparation method of P (Allyl-beta-CD)/PSA microspheres and application of P (Allyl-beta-CD)/PSA microspheres in adsorption of cinchonine |
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