CN102527339B - Organic porous gel absorbent, preparation method and application thereof - Google Patents
Organic porous gel absorbent, preparation method and application thereof Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 239000002250 absorbent Substances 0.000 title abstract 10
- 230000002745 absorbent Effects 0.000 title abstract 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 30
- SWVMLNPDTIFDDY-FVGYRXGTSA-N methyl (2s)-2-amino-3-phenylpropanoate;hydrochloride Chemical compound Cl.COC(=O)[C@@H](N)CC1=CC=CC=C1 SWVMLNPDTIFDDY-FVGYRXGTSA-N 0.000 claims abstract description 10
- 238000004065 wastewater treatment Methods 0.000 claims abstract description 10
- 239000003463 adsorbent Substances 0.000 claims description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 238000001556 precipitation Methods 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 4
- 239000008367 deionised water Substances 0.000 claims description 3
- 229910021641 deionized water Inorganic materials 0.000 claims description 3
- 235000019441 ethanol Nutrition 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 238000002390 rotary evaporation Methods 0.000 claims description 3
- 238000001291 vacuum drying Methods 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000000975 dye Substances 0.000 abstract description 38
- 238000001179 sorption measurement Methods 0.000 abstract description 23
- 238000004043 dyeing Methods 0.000 abstract description 8
- 239000002351 wastewater Substances 0.000 abstract description 8
- JCZLABDVDPYLRZ-AWEZNQCLSA-N biphenylalanine Chemical compound C1=CC(C[C@H](N)C(O)=O)=CC=C1C1=CC=CC=C1 JCZLABDVDPYLRZ-AWEZNQCLSA-N 0.000 abstract description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 6
- 229910052799 carbon Inorganic materials 0.000 abstract description 6
- 239000010842 industrial wastewater Substances 0.000 abstract description 6
- FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 abstract description 5
- 238000007639 printing Methods 0.000 abstract description 5
- 238000011084 recovery Methods 0.000 abstract description 5
- 230000003993 interaction Effects 0.000 abstract description 2
- 239000000499 gel Substances 0.000 description 32
- 239000000017 hydrogel Substances 0.000 description 14
- RBTBFTRPCNLSDE-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazin-5-ium Chemical compound C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 RBTBFTRPCNLSDE-UHFFFAOYSA-N 0.000 description 13
- 238000010521 absorption reaction Methods 0.000 description 13
- 229960000907 methylthioninium chloride Drugs 0.000 description 13
- 239000013078 crystal Substances 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 239000002594 sorbent Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000010919 dye waste Substances 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000007539 photo-oxidation reaction Methods 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
The invention relates to an organic porous gel absorbent for quick treatment of dye wastewater in printing and dyeing industry, a preparation method and application of the organic porous gel absorbent. The organic porous gel absorbent is 1,4-phenyl phenylalanine. The preparation method comprises the steps of preparing 1,4-phenyl phenylalanine methyl ester from phthaloyl chloride, L-phenylalanine methyl ester hydrochloride and triethylamine; and preparing the dyeing absorbent 1,4-phenyl phenylalanine from 1,4-phenyl phenylalanine methyl ester. The invention also relates to the application of the organic porous gel absorbent as a quick absorbent in dye wastewater treatment. The organic porous gel absorbent provided by the invention is a low-molecular-weight gel absorbent with an active carbon porous structure, and can rapidly and efficiently capture dyes in the industrial wastewater through phi-phi interaction, with the advantages of easy recovery and low cost. The dye adsorption can be conducted by simple operation at normal temperature, so that the organic porous gel absorbent has actual application value.
Description
Technical field
The present invention relates to adsorbent in a kind of technical field of textile industry and preparation method thereof, purposes, relate in particular to a kind of organic porous gel adsorbent for printing and dyeing industry fast processing waste water from dyestuff and preparation method thereof, purposes.
Background technology
Developing rapidly of textile and dyeing industry caused severe contamination to the water environment of China.According to incompletely statistics, annual dyestuff with the waste formation discharging has 60,000 tons.These waste water from dyestuff often contain multiple organic dyestuff and intermediate, the concentration height, and colourity is dark, strong toxicity, difficult degradation.They have constituted serious day by day threat to water ecological setting.Therefore the processing of dying industrial wastewater has become a current big problem of being badly in need of solution both at home and abroad.Industrial dye waste water treatment method commonly used has absorption method, Coagulation Method, oxidizing process, electrolysis, photooxidation and sonication etc.Absorption method wherein because easy to operate, energy consumption is low, dyestuff is removed the efficient height, it is good that it handles back water quality, is widely used in the dye wastewater treatment field.Industrial the most frequently used dye sorbent is active carbon at present.But active carbon adsorption is a kind of method of using early, and water-soluble organic dyestuff is very effective for removing, but the charcoal absorption time is longer, the regeneration difficulty, and post processing cost height makes its application limited.
Summary of the invention
The object of the present invention is to provide a kind of organic porous gel adsorbent for printing and dyeing industry fast processing waste water from dyestuff and preparation method thereof, purposes.Organic porous gel adsorbent of the present invention is a kind of low-molecular-weight gel adsorber with active carbon loose structure; This organogel adsorbent interacts by π-π, can catch the dyestuff in the industrial wastewater quickly and efficiently, and the adsorbent recovery easily, and is with low cost.The dyestuff adsorption process is carried out at normal temperatures, and is easy to operate, has actual application value.
The present invention realizes by following technical scheme,
The present invention relates to a kind of organic porous gel adsorbent, described adsorbent is 1,4-phenyl phenylalanine, and its structural formula is shown below:
The present invention also provides aforementioned organic porous gel preparation of adsorbent method, comprises the steps:
(a) get phthalyl chloride, L-phenylalanine methyl ester hydrochloride, triethylamine;
(b) with the anhydrous methylene chloride solution cooling of L-phenylalanine methyl ester hydrochloride, add triethylamine, add the anhydrous methylene chloride solution of paraphthaloyl chloride again, get reaction solution; Reaction solution is slowly risen to room temperature and stirring;
(c) rotary evaporation reactant liquor adds deionized water, filters collecting precipitation, gained precipitation ethyl alcohol recrystallization, and filtration is also dry in baking oven, gets product 1,4-phenyl phenyalanine methyl ester;
(d) add the 2M sodium hydroxide solution in the methanol solution of 1,4-phenyl phenyalanine methyl ester, reactant mixture is stirring reaction at room temperature, with the 3M hydrochloric acid solution reacting liquid pH value is transferred to less than 3, filter and collect precipitation and the vacuum drying of generating, obtain dye sorbent 1,4-phenyl phenylalanine.
Preferably, in the step (a), the mol ratio of described phthalyl chloride, L-phenylalanine methyl ester hydrochloride, triethylamine is 1: 2: 6.
Preferably,, in the step (b), described being cooled to is cooled to 0 ℃, and the time of described stirring is 12～16 hours.
Preferably, in the step (d), the described stirring reaction time is 20～24 hours.
The present invention also relates to aforementioned organic porous gel adsorbent purposes as quick adsorbent in dye wastewater treatment simultaneously.
The present invention has following beneficial effect: organic porous gel adsorbent of the present invention is a kind of low-molecular-weight gel adsorber with active carbon loose structure; This organogel adsorbent interacts by π-π, can catch the dyestuff in the industrial wastewater quickly and efficiently; Gel adsorber is intermolecular to be non-covalent interaction such as hydrogen bond, thus adsorbent reclaim easily, with low cost.The dyestuff adsorption process is carried out at normal temperatures, and is easy to operate, has actual application value; The organic porous gel preparation of adsorbent of the present invention method need not complicated synthesis step, is easy to industrial production in enormous quantities, products therefrom purity height, and good dispersion is suitable for industrialization waste water from dyestuff is handled.Organic porous gel adsorbent of the present invention can effectively be handled organic dyestuff industrial wastewaters such as containing methylene blue, crystal violet; Waste water from dyestuff mixed with gel adsorber after 30 seconds filter, the dyestuff clearance is higher than 98%.
Description of drawings
Fig. 1 is the final compound of embodiment 1 preparation
1The HNMR spectrogram;
Fig. 2 is the EI-MS spectrogram of the final compound of embodiment 1 preparation;
Fig. 3 is that gel adsorber is to the methylene blue adsorption process;
Fig. 4 is methylene blue ultraviolet-visible spectrogram (going up to before handling, down for handling the back) before and after adsorption treatment;
Fig. 5 is that gel adsorber is to crystal violet adsorption process comparison diagram;
Fig. 6 is crystal violet ultraviolet-visible spectrogram (going up to before handling, down for handling the back) before and after adsorption treatment;
Fig. 7 is comparison diagram before and after the adsorbent equipment absorption wastewater treatment
Fig. 8 is ultraviolet-visible spectrogram before and after the treatment of dyeing wastewater (going up to before handling, down for handling the back);
Fig. 9 is the gel adsorber removal process.
The specific embodiment
The present invention is described in detail below in conjunction with specific embodiment.Following examples will help those skilled in the art further to understand the present invention, but not limit the present invention in any form.Should be pointed out that to those skilled in the art, without departing from the inventive concept of the premise, can also make some distortion and improvement.These all belong to protection scope of the present invention.
Present embodiment prepares organic porous gel adsorbent and comprises the steps:
(a) get phthalyl chloride, L-phenylalanine methyl ester hydrochloride, triethylamine; The mol ratio of described phthalyl chloride, L-phenylalanine methyl ester hydrochloride, triethylamine is 1: 2: 6; Described raw material all can obtain from disclosed commercially available channel;
(b) the anhydrous methylene chloride solution with the L-phenylalanine methyl ester hydrochloride is cooled to 0 ℃, adds triethylamine, adds the anhydrous methylene chloride solution of paraphthaloyl chloride again, gets reaction solution; Reaction solution is slowly risen to room temperature and stirred 12～16 hours;
(c) rotary evaporation reactant liquor adds deionized water, filters collecting precipitation, gained precipitation ethyl alcohol recrystallization, filter and in baking oven drying 10 to 12 hours, 50 ℃ to 60 ℃ of baking temperatures get product 1,4-phenyl phenyalanine methyl ester;
(d) to 1, add the 2M sodium hydroxide solution in the methanol solution of 4-phenyl phenyalanine methyl ester, reactant mixture is stirring reaction 20～24 hours at room temperature, with the 3M hydrochloric acid solution reacting liquid pH value is transferred to less than 3, filter and collect precipitation and the vacuum drying of generating, obtain dye sorbent 1,4-phenyl phenylalanine;
1HNMR (400MHz, DMSO-d6, δ): δ=3.2 (d, 4H, CH2), 4.6 (s, 2H, CH), and 7.3 (q, 10H, Ar H), 7.8 (s, 4H, Ar H), 8.8 (d, 2H, NH), 12.8 (s, 2H, OH) ppm.
1The HNMR spectrogram as shown in Figure 1.EI-MS:C
26H
24O
6N
2Calcd:460.49; Found 460.17[M
+] the .EI-MS spectrogram as shown in Figure 2.The structure of compound is shown below:
Embodiment 2, organic porous gel adsorbent purposes
2.1 the absorption to methylene blue
At first 36.6mg gel adsorber powder is dissolved in the 1ml sodium hydroxide solution (2M), add 10ml hydrochloric acid solution (0.3M) again and make 11ml hydrogel (3.33mg/ml), in hydrogel, add 4ml methylene blue solution (0.1mg/ml) and mix the back and filter with the pin type filter, after treatment this adsorbent to the methylene blue adsorption rate up to 97.61%.Adsorption process is seen Fig. 3: xerogel adds hcl acidifying and becomes hydrogel after dissolving with sodium hydroxide solution; In hydrogel, add methylene blue and mix with gel; With the pin type filter hydrogel and dyestuff mixed liquor are filtered; Respectively the filtrate after the test water Gel Treatment (see Fig. 4: methylene blue characteristic absorption peak intensity is 0.0537 in the filtrate after hydrogel is handled with ultraviolet-visible spectrogram without the former dye solution of adsorption treatment, be 2.2443 without methylene blue characteristic absorption peak intensity in the former dye solution of adsorption treatment, must this gel adsorber be 97.61% to the adsorption rate of methylene blue).
2.2 the absorption to crystal violet
The 11ml hydrogel adsorbent (3.33mg/ml) of 2.1 steps preparations as described above adds 4ml crystal violet solution (0.1mg/ml) and mixes the back and filter with the pin type filter in hydrogel, after treatment this adsorbent to the methylene blue adsorption rate up to 97.98%.Adsorption process is seen Fig. 5: xerogel adds hcl acidifying and becomes hydrogel after dissolving with sodium hydroxide solution; In hydrogel, add crystal violet and mix with gel; With the pin type filter hydrogel and dyestuff mixed liquor are filtered; Respectively the filtrate after the test water Gel Treatment (see Fig. 6: crystal violet characteristic absorption peak intensity is 0.0305 in the filtrate after hydrogel is handled with ultraviolet-visible spectrogram without the former dye solution of adsorption treatment, be 1.5125 without crystal violet characteristic absorption peak intensity in the former dye solution of adsorption treatment, must this gel adsorber be 97.98% to the adsorption rate of crystal violet).
2.3 dynamic method is to printing and dyeing mill's wastewater treatment
The 11ml hydrogel adsorbent (3.33mg/ml) of 2.1 steps preparation is tiled in the sand core funnel as described above, pours 10ml printing and dyeing mill waste water in funnel filtration under diminished pressure.This adsorbent can reach 73.4% to dyestuff moment adsorption rate after treatment.Before and after the adsorbent equipment, wastewater treatment comparison diagram as shown in Figure 7 (left side: adsorbent equipment, in: before the wastewater treatment, the right side: after the wastewater treatment).The adsorption rate data utilize uv-vis spectra to record specifically to see Fig. 8, and (dyestuff characteristic absorption peak intensity is 0.0808 in the filtrate after hydrogel is handled, be 0.3034 without dyestuff characteristic absorption peak intensity in the former dye solution of adsorption treatment, must this gel adsorber be 73.4% to the adsorption rate of dyestuff).
The recycling of embodiment 3, organic porous gel adsorbent
The adsorbent that 500mg has been adsorbed methylene blue is dissolved in the 5ml sodium hydroxide solution, adds the 35ml chloroform again and extracts, and gets upper water solution, adds the hydrochloric acid solution acidifying and becomes gel, filter, and drying, the rate of recovery can reach 90%.Removal process is seen Fig. 9: after the 500mg dye sorbent was used for the absorption methylene blue dye, after dissolution of sodium hydroxide, chloroform extraction, hcl acidifying, filtration, drying, it was 450mg that quality is reclaimed in weighing, and the rate of recovery is 90%.
In sum, organic porous gel adsorbent of the present invention is a kind of low-molecular-weight gel adsorber with active carbon loose structure; This organogel adsorbent interacts by π-π, can catch the dyestuff in the industrial wastewater quickly and efficiently, and the adsorbent recovery easily, and is with low cost.The dyestuff adsorption process is carried out at normal temperatures, and is easy to operate, has actual application value.
Claims (6)
1. organic porous gel adsorbent is characterized in that the structural formula of described adsorbent is shown below:
2. a method for preparing organic porous gel adsorbent as claimed in claim 1 is characterized in that, comprises the steps:
(a) get paraphthaloyl chloride, L-phenylalanine methyl ester hydrochloride, triethylamine;
(b) with the anhydrous methylene chloride solution cooling of L-phenylalanine methyl ester hydrochloride, add triethylamine, add the anhydrous methylene chloride solution of paraphthaloyl chloride again, get reaction solution; Reaction solution is slowly risen to room temperature and stirring;
(c) rotary evaporation reactant liquor adds deionized water, filters collecting precipitation, gained precipitation ethyl alcohol recrystallization, and filtration is also dry in baking oven, gets product;
(d) add the 2M sodium hydroxide solution in the methanol solution of described product, reactant mixture is stirring reaction at room temperature, with the 3M hydrochloric acid solution reacting liquid pH value is transferred to less than 3, filters and collects precipitation and the vacuum drying of generating, and obtains described adsorbent.
3. preparation method as claimed in claim 2 is characterized in that, in the step (a), the mol ratio of described paraphthaloyl chloride, L-phenylalanine methyl ester hydrochloride, triethylamine is 1:2:6.
4. preparation method as claimed in claim 3 is characterized in that, in the step (b), described being cooled to is cooled to 0 ℃, and the time of described stirring is 12～16 hours.
5. preparation method as claimed in claim 3 is characterized in that, in the step (d), the described stirring reaction time is 20～24 hours.
Organic porous gel adsorbent as claimed in claim 1 in dye wastewater treatment as the quick purposes of adsorbent.
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| CN110025827B (en) * | 2019-03-27 | 2020-09-15 | 上海交通大学 | Water-retaining two-component hydrogel containing natural plant polysaccharide and preparation method and application thereof |
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| CN101298038A (en) * | 2008-03-13 | 2008-11-05 | 西南石油大学 | Gel adsorbing agent for wastewater treatment |
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| CN101298038A (en) * | 2008-03-13 | 2008-11-05 | 西南石油大学 | Gel adsorbing agent for wastewater treatment |
Non-Patent Citations (5)
| Title |
|---|
| Introducing chemical functionality in Fmoc-peptide gels for cell culture;Vineetha Jayawarna, et al.;《Acta Biomaterialia》;20090118;第5卷;第934-943页 * |
| JP特开2007-237097A 2007.09.20 |
| Vineetha Jayawarna, et al..Introducing chemical functionality in Fmoc-peptide gels for cell culture.《Acta Biomaterialia》.2009,第5卷第934-943页. |
| 低分子量凝胶的研究进展及展望;窦晓秋等;《科学技术与工程》;20110131;第11卷(第2期);第286-295页 * |
| 窦晓秋等.低分子量凝胶的研究进展及展望.《科学技术与工程》.2011,第11卷(第2期),第286-295页. |
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Effective date of registration: 20231215 Address after: 201401 5th Floor, Building 12, No. 88, Chengpu Road, Fengxian District, Shanghai Patentee after: Shanghai Kaihejiao Medical Technology Co.,Ltd. Address before: 200240 800 Dongchuan Road, Shanghai, Minhang District, Shanghai. Patentee before: SHANGHAI JIAO TONG University |