CN103087246B - A kind of containing ester group adsorbent resin with high specific surface area and preparation method thereof - Google Patents
A kind of containing ester group adsorbent resin with high specific surface area and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a kind of containing ester group adsorbent resin with high specific surface area and preparation method thereof, belong to high-molecular adsorption resin field.The particle diameter of resin of the present invention is 0.3-0.85mm, and water ratio is 55-65%, and specific surface area is greater than 600m
2/ g.Its preparation process is: 1) dispersion agent and NaCl are made into aqueous phase; 2) vinylbenzene, ester class linking agent, pore-creating agent, conditioning agent, initiator are made into organic phase; 3) aqueous phase and organic phase are successively added in reactor, be stirred to organic phase in aqueous phase, be separated into temperature reaction after appropriate particle size, obtain resin intermediate; 4) inertia swelling agent resin intermediate is fully swelling after, add lewis acid catalyst, temperature reaction, be then cooled to room temperature, steam swelling agent, wash and dry.Resin specific surface area of the present invention is high, large to Adsorption of Organic capacity, can effectively for improvement and the resource utilization of high content of salt organic waste water; And the preparation process of this resin is simple, its pore-creating agent and swelling agent all can reuses.
Description
Technical field
The present invention relates to preparation and preparation method thereof technical field, more particularly, relate to a kind of containing ester group adsorbent resin with high specific surface area and preparation method thereof.
Background technology
Resin absorption isolation technique has the advantages such as technique is simple, working cost is low, the renewable use of resin, environmental friendliness due to it, in recent years, in the improvement being widely used in wastewater from chemical industry and resource utilization, and the particularly organic chemical waste water of some difficult for biological degradation.Such as, the improvement of the waste water that salts contg is high, dissolved organic matter concentration is high, acid-basicity is strong is the study hotspot of resin method always.Adopt hydrophobic polymeric adsorbent to be difficult to the higher organism of planar water dissolubility, and the ion exchange resin adopting polarity stronger can be subject to the interference of salt.Studies have found that, adopt the Semi-polarity polymeric adsorbent containing ester group from the acid waste water of high content of salt, selective adsorption can be separated Sulfonates organism (Pan, B.J.; Zhang, W.M.; Pan, B.C.; Qiu, H.; ZhangQ.R.; Zhang, Q.X.; ZhengS.R.Environ.Sci.Technol.2008,42,7411 – 7416), its dominant mechanism is that ester group is protonated in acid condition, and forms electrostatic attraction with sulfonic group negatively charged ion.In addition, water soluble organic substance pollutent is mostly containing various polar group (e.g. ,-COOH ,-NH
2,-OH etc.), these groups can form hydrogen bond action with ester group, therefore, have higher adsorption selectivity containing ester group polymeric adsorbent to these water soluble organic substances.But the most specific surface area of this resinoid is lower, only has 500m
2about/g (e.g., ROHM AND HAAS popular commercial product A mberliteXAD-7).Resin specific surface area is low, directly affects the adsorptive capacity of resin, makes regeneration more frequent, thus adds working cost.
Rear crosslinking be improve resin specific surface area the method commonly used, traditional phenylethylene resin series skeleton by chloromethylation, the alkylating post-crosslinking reaction of fourier improve the specific surface area (DavankovV.A. of polymeric adsorbent; RogozhinS.V.; TsyurupaM.P.Polym.Sci.Polym.Symp, 1974,47:95-102), but the method is only limitted to styrene-divinylbenzene system resin matrix.
Summary of the invention
1. invent the technical problem that will solve
The present invention is directed to containing the generally lower defect of the Semi-polarity polymeric adsorbent specific surface area of ester group, provide a kind of containing ester group adsorbent resin with high specific surface area and preparation method thereof, by the present invention can synthesis ratio surface-area high, to Adsorption of Organic resin capacious.
2. technical scheme
For achieving the above object, technical scheme provided by the invention is:
One of the present invention is containing ester group adsorbent resin with high specific surface area, and its structural unit is as follows:
Wherein R is: H or CH
3.
The constitutional features of resin is opaque or translucent spherical beaded, and particle diameter is 0.3-0.85mm, and water ratio is 55-65%, and specific surface area is greater than 600m
2/ g.
A kind of preparation method containing ester group adsorbent resin with high specific surface area of the present invention, the steps include:
1) under normal temperature, dispersion agent and NaCl are dissolved in the water, are made into aqueous phase, wherein percent mass hundred concentration of dispersion agent and NaCl is respectively 0.5-1% and 5-10%;
2) organic phase is made up of vinylbenzene, ester class linking agent, pore-creating agent, conditioning agent, initiator, wherein vinylbenzene and ester group linking agent anabolic reaction thing, and both mass ratioes are: 1:1-1:3; The mass ratio of pore-creating agent and reactant is: 1:1-4:1; The mass ratio of conditioning agent and reactant is: 0-1:10; The mass ratio of initiator and reactant is: 1:150-1:50, above-mentioned organic phase is mixed, dissolves completely to initiator;
3) poured in reactor by aqueous phase, then pour in reactor by organic phase, the volume ratio of aqueous phase and organic phase is 1:2-2:1; Pass into nitrogen purging reactor 5-10 minute, close nitrogen after purging and start to stir, stirring velocity is 100-250rpm, makes organic phase in aqueous phase, be dispersed into the oil droplet of 300-900 μm, be warming up to 50-75 DEG C, react 2 hours, then continue to be warming up to 80-95 DEG C, react after 5-15 hour and stop heating, keep being stirred to temperature and reduce to room temperature, then continuing progressively raised temperature, steam pore-creating agent, obtaining resin intermediate through washing also drying;
4) above-mentioned resin intermediate is proceeded in reactor, after heated inert solvent is fully swelling, add the lewis acid catalyst of 10-30% resin intermediate quality, be warming up to 75-125 DEG C, react after 2-15 hour and stop heating, keep being stirred to temperature and drop to room temperature, then progressively raised temperature is continued, steam swelling agent, washing resin is also dried, and obtains containing ester group adsorbent resin with high specific surface area.
Containing a preparation method for ester group adsorbent resin with high specific surface area, dispersion agent described in step 1) is one or both the mixture in gelatin, polyvinyl alcohol, methylcellulose gum, Natvosol or methylhydroxypropylcellulose.
Containing the preparation method of ester group adsorbent resin with high specific surface area, step 2) described in ester group linking agent be one or both mixture in diethyleneglycol dimethacrylate(DEGDMA), allyl methacrylate(AMA), cyamelide allyl ester or allyl itaconates; Step 2) in pore-creating agent be one in isopropylcarbinol, primary isoamyl alcohol, toluene, dimethylbenzene, enanthol or hexalin; Step 2) in conditioning agent be diethylene glycol dimethyl ether, pentan-thiol, toluene dichloride, divinylbenzene, 2, the mixture of one or more in two (allyloxymethyl)-butane-1 alcohol of 2-or oleic acid, the effect of conditioning agent improves crosslinked homogeneity, can add a certain amount of as required or not add, in the present invention, the mass ratio of conditioning agent and reactant is: 0-0.1; Step 2) in initiator be one or both mixture in benzoyl peroxide, Diisopropyl azodicarboxylate or azo-bis-iso-dimethyl.
Containing a preparation method for ester group adsorbent resin with high specific surface area, the swelling agent of inertia described in step 3) is the one in tetracol phenixin, zellon, oil of mirbane, 1,2-ethylene dichloride or sym.-tetrachloroethane; Lewis acid catalyst in step 3) is the one in aluminum chloride, zinc dichloride, tin tetrachloride, Indium-111 chloride, iron trichloride or trimethylchlorosilane.
3. beneficial effect
Adopt technical scheme provided by the invention, compared with existing known technology, there is following unusual effect:
The present invention utilizes vinylbenzene and ester group linking agent to synthesize polymeric adsorbent compared with low specific surface area, residual suspended double bond in recycling resin matrix and the alkylating post-crosslinking reaction of phenyl ring generation fourier in resin matrix, obtain of the present invention containing ester group adsorbent resin with high specific surface area, the specific surface area of this resin is greater than 600m
2/ g, its physical strength is higher than general ester group polymeric adsorbent.This resin can be used for high content of salt, the improvement of organic chemical waste water of highly water-soluble and resource utilization.A kind of preparation method's step containing ester group adsorbent resin with high specific surface area of the present invention is simple, and required equipment is simple and easy, and desired raw material cheaply, is easily purchased, and the pore-creating agent in synthesis and swelling agent all can reuses.
Accompanying drawing explanation
Fig. 1 is that the Fourier containing ester group adsorbent resin with high specific surface area in embodiment 1 changes infrared spectrum;
Fig. 2 is containing the aperture of ester group adsorbent resin with high specific surface area and differential pore volume distribution plan in embodiment 1.
Embodiment
For understanding content of the present invention further, the present invention is described in detail in conjunction with the accompanying drawings and embodiments.
embodiment 1
In 1000 milliliters of four-hole boiling flasks, add 252g deionized water, 1.4g gelatin, 26.5gNaCl, stir and be heated to 35 DEG C, dissolving completely to gelatin and NaCl, close and stir standing 5 minutes.After 25g vinylbenzene, 75g diethyleneglycol dimethacrylate(DEGDMA), 250g toluene, 9g divinylbenzene (mass percent 80%), 1g pentan-thiol, 2g benzoyl peroxide are mixed, add in four-hole boiling flask.Pass into nitrogen purging 5 minutes, close nitrogen, start to stir, stirring velocity is 150rpm, after the oil droplet that organic phase is dispersed into 300-900 μm of particle diameter in aqueous phase, is warming up to 72 DEG C, reacts 2 hours, continues to be warming up to 85 DEG C, reacts 10 hours.Stop heating, keep being stirred to temperature and reduce to room temperature.Then continue to heat up, steam toluene, washing, discharging obtains resin intermediate.55 DEG C of vacuum-dryings are after 6 hours, and it is swelling to add 5 times of 1,2-ethylene dichloride to resin intermediate quality, after swelling 5 hours, adds the Aluminum chloride anhydrous of 25% resin intermediate quality, stirs after 1 hour, be warming up to 84 DEG C, react 10 hours.Stop heating, keep being stirred to temperature and reduce to room temperature.Continue to heat up, steam ethylene dichloride, washing, discharging, 55 DEG C of vacuum-drying 6 hours, obtain of the present invention containing ester group adsorbent resin with high specific surface area.
Show after testing, should be light yellow, semi-transparent spheres containing the outward appearance of ester group adsorbent resin with high specific surface area, particle diameter be 0.3-0.85mm, and water content is 61.5%, and mean pore size is 2.4nm, and specific surface area is 746.5m
2/ g.The Fourier transform infrared spectrogram of gained resin, as in Fig. 1, figure at 3000cm
-1and 1450cm
-1place has the charateristic avsorption band of hydrogen and phenyl ring on phenyl ring respectively, proves the existence of phenyl ring in resin matrix.1730 and 1160cm
-1place has the carbon oxygen base charateristic avsorption band of carbonyl and ester group respectively, proves the existence of ester group in resin matrix.At 710-900cm
-1two replacement charateristic avsorption bands that place is phenyl ring, prove that the cinnamic phenyl ring in resin matrix there occurs further substitution reaction.The aperture of gained resin and differential pore volume graph of a relation, the aperture as shown resin in Fig. 2, figure is mainly distributed in about 2nm.
embodiment 2
In 1000 milliliters of four-hole boiling flasks, add 400g deionized water, 3g gelatin, 22gNaCl, stir and be heated to 35 DEG C, dissolving completely to gelatin and NaCl, close and stir standing 5 minutes.After 50g vinylbenzene, 50g diethyleneglycol dimethacrylate(DEGDMA), 100g primary isoamyl alcohol, 1.2g benzoyl peroxide are mixed, add in four-hole boiling flask.Pass into nitrogen purging 5 minutes, close nitrogen, start to stir, stirring velocity is 150rpm, after the oil droplet that organic phase is dispersed into 300-900 μm of particle diameter in aqueous phase, is warming up to 72 DEG C, reacts 2 hours, continues to be warming up to 85 DEG C, reacts 10 hours.Stop heating, keep being stirred to temperature and reduce to room temperature.Then continue to heat up, steam primary isoamyl alcohol, washing, discharging obtains resin intermediate.55 DEG C of vacuum-dryings are after 6 hours, and it is swelling to add 5 times of 1,2-ethylene dichloride to resin intermediate quality, after swelling 5 hours, adds the Anhydrous Ferric Chloride of 20% resin intermediate quality, stirs after 1 hour, be warming up to 84 DEG C, react 10 hours.Stop heating, keep being stirred to temperature and reduce to room temperature.Continue to heat up, steam ethylene dichloride, washing, discharging, 55 DEG C of vacuum-drying 6 hours, obtain of the present invention containing ester group adsorbent resin with high specific surface area.
Show after testing, should be light brown, opaque spheroid containing the outward appearance of ester group adsorbent resin with high specific surface area, particle diameter be 0.3-0.85mm, and water content is 58.3%, and mean pore size is 2.9nm, and specific surface area is 655.7m
2/ g.
embodiment 3
In 1000 milliliters of four-hole boiling flasks, add 250g deionized water, 1.8g gelatin, 20gNaCl, stir and be heated to 35 DEG C, dissolving completely to gelatin and NaCl, close and stir standing 5 minutes.After 35g vinylbenzene, 65g allyl methacrylate(AMA), 400g dimethylbenzene, two (allyloxymethyl)-butane-1 alcohol of 5g2,2-, 0.5g benzoyl peroxide, 1.1g Diisopropyl azodicarboxylate are mixed, add in four-hole boiling flask.Pass into nitrogen purging 5 minutes, close nitrogen, start to stir, stirring velocity is 150rpm, after the oil droplet that organic phase is dispersed into 300-900 μm of particle diameter in aqueous phase, is warming up to 72 DEG C, reacts 2 hours, continues to be warming up to 85 DEG C, reacts 10 hours.Stop heating, keep being stirred to temperature and reduce to room temperature.Then continue to heat up, steam dimethylbenzene, washing, discharging obtains resin intermediate.55 DEG C of vacuum-dryings, after 6 hours, add 5 times to the tetrachloroethane of resin intermediate quality, after swelling 5 hours, add the Aluminum chloride anhydrous of 30% resin intermediate quality, stir after 1 hour, are warming up to 120 DEG C, react 10 hours.Stop heating, keep being stirred to temperature and reduce to room temperature.Continue to heat up, steam tetrachloroethane, washing, discharging, 55 DEG C of vacuum-drying 6 hours, obtain of the present invention containing ester group adsorbent resin with high specific surface area.
Show after testing, should be light yellow, semi-transparent spheres containing the outward appearance of ester group adsorbent resin with high specific surface area, particle diameter be 0.3-0.85mm, and water content is 64.2%, and mean pore size is 1.6nm, and specific surface area is 793.6m
2/ g.
embodiment 4
In 1000 milliliters of four-hole boiling flasks, add 245g deionized water, 2g gelatin, 13gNaCl, stir and be heated to 35 DEG C, dissolving completely to gelatin and NaCl, close and stir standing 5 minutes.After 45g vinylbenzene, 55g allyl methacrylate(AMA), 200g toluene, two (allyloxymethyl)-butane-1 alcohol of 5g2,2-, 0.5g benzoyl peroxide, 0.9g Diisopropyl azodicarboxylate are mixed, add in four-hole boiling flask.Pass into nitrogen purging 5 minutes, close nitrogen, start to stir, stirring velocity is 150rpm, after the oil droplet that organic phase is dispersed into 300-900 μm of particle diameter in aqueous phase, is warming up to 72 DEG C, reacts 2 hours, continues to be warming up to 85 DEG C, reacts 10 hours.Stop heating, keep being stirred to temperature and reduce to room temperature.Then continue to heat up, steam toluene, washing, discharging obtains resin intermediate.55 DEG C of vacuum-dryings are after 6 hours, and it is swelling to add 5 times of 1,2-ethylene dichloride to resin intermediate quality, after swelling 5 hours, adds the Anhydrous Ferric Chloride of 20% resin intermediate quality, stirs after 1 hour, be warming up to 84 DEG C, react 10 hours.Stop heating, keep being stirred to temperature and reduce to room temperature.Continue to heat up, steam ethylene dichloride, washing, discharging, 55 DEG C of vacuum-drying 6 hours, obtain of the present invention containing ester group adsorbent resin with high specific surface area.
Show after testing, should be light brown, opaque spheroid containing the outward appearance of ester group adsorbent resin with high specific surface area, particle diameter be 0.3-0.85mm, and water content is 60.2%, and mean pore size is 2.5nm, and specific surface area is 711.8m
2/ g.
embodiment 5
In 2000 milliliters of four-hole boiling flasks, add 445g deionized water, 4g gelatin, 1g Natvosol, 50gNaCl, stir and be heated to 35 DEG C, dissolving completely to gelatin and NaCl, close and stir standing 5 minutes.After 95g vinylbenzene, 100g allyl methacrylate(AMA), 360g toluene, two (allyloxymethyl)-butane-1 alcohol of 10g2,2-, 1.3g Diisopropyl azodicarboxylate are mixed, add in four-hole boiling flask.Pass into nitrogen purging 5 minutes, close nitrogen, start to stir, stirring velocity is 150rpm, after the oil droplet that organic phase is dispersed into 300-900 μm of particle diameter in aqueous phase, is warming up to 72 DEG C, reacts 2 hours, continues to be warming up to 85 DEG C, reacts 10 hours.Stop heating, keep being stirred to temperature and reduce to room temperature.Then continue to heat up, steam toluene, washing, discharging obtains resin intermediate.55 DEG C of vacuum-dryings are after 6 hours, and it is swelling to add 5 times of 1,2-ethylene dichloride to resin intermediate quality, after swelling 5 hours, adds the Anhydrous Ferric Chloride of 10% resin intermediate quality, stirs after 1 hour, be warming up to 84 DEG C, react 10 hours.Stop heating, keep being stirred to temperature and reduce to room temperature.Continue to heat up, steam ethylene dichloride, washing, discharging, 55 DEG C of vacuum-drying 6 hours, obtain of the present invention containing ester group adsorbent resin with high specific surface area.
Show after testing, should be light brown, opaque spheroid containing the outward appearance of ester group adsorbent resin with high specific surface area, particle diameter be 0.3-0.85mm, and water content is 59.5%, and mean pore size is 2.8nm, and specific surface area is 673.7m
2/ g.
embodiment 6
In 2000 milliliters of four-hole boiling flasks, add 500g deionized water, 3.5g gelatin, 1g Natvosol, 40gNaCl, stir and be heated to 35 DEG C, dissolving completely to gelatin and NaCl, close and stir standing 5 minutes.By 90g vinylbenzene, 20g allyl methacrylate(AMA), 90g allyl itaconates, 360g toluene, 10g divinylbenzene (mass percent 80%), 8g2, after two (allyloxymethyl)-butane-1 alcohol of 2-, 1g pentan-thiol, 1g diethylene glycol dimethyl ether, 1.9g Diisopropyl azodicarboxylate mix, add in four-hole boiling flask.Pass into nitrogen purging 5 minutes, close nitrogen, start to stir, stirring velocity is 150rpm, after the oil droplet that organic phase is dispersed into 300-900 μm of particle diameter in aqueous phase, is warming up to 72 DEG C, reacts 2 hours, continues to be warming up to 85 DEG C, reacts 10 hours.Stop heating, keep being stirred to temperature and reduce to room temperature.Then continue to heat up, steam toluene, washing, discharging obtains resin intermediate.55 DEG C of vacuum-dryings are after 6 hours, and it is swelling to add 5 times of 1,2-ethylene dichloride to resin intermediate quality, after swelling 5 hours, adds the Aluminum chloride anhydrous of 20% resin intermediate quality, stirs after 1 hour, be warming up to 84 DEG C, react 10 hours.Stop heating, keep being stirred to temperature and reduce to room temperature.Continue to heat up, steam ethylene dichloride, washing, discharging, 55 DEG C of vacuum-drying 6 hours, obtain of the present invention containing ester group adsorbent resin with high specific surface area.
Show after testing, should be faint yellow, semi-transparent spheres containing the outward appearance of ester group adsorbent resin with high specific surface area, particle diameter be 0.3-0.85mm, and water content is 60.9%, and mean pore size is 1.9nm, and specific surface area is 738.5m
2/ g.
Claims (5)
1., containing an ester group adsorbent resin with high specific surface area, it is characterized in that its structural unit is as follows:
Wherein R is: H or CH
3;
Should be containing preparation method's step of ester group adsorbent resin with high specific surface area:
1) under normal temperature, dispersion agent and NaCl are dissolved in the water, are made into aqueous phase, wherein percent mass hundred concentration of dispersion agent and NaCl is respectively 0.5-1% and 5-10%;
2) organic phase is made up of vinylbenzene, ester group linking agent, pore-creating agent, conditioning agent, initiator, wherein vinylbenzene and ester group linking agent anabolic reaction thing, and both mass ratioes are: 1:1-1:3; The mass ratio of pore-creating agent and reactant is: 1:1-4:1; The mass ratio of conditioning agent and reactant is: 0-1:10; The mass ratio of initiator and reactant is: 1:150-1:50, above-mentioned organic phase is mixed, dissolves completely to initiator;
3) poured in reactor by aqueous phase, then pour in reactor by organic phase, the volume ratio of aqueous phase and organic phase is 1:2-2:1; Pass into nitrogen purging reactor 5-10 minute, close nitrogen after purging and start to stir, stirring velocity is 100-250rpm, makes organic phase in aqueous phase, be dispersed into the oil droplet of 300-900 μm, be warming up to 50-75 DEG C, react 2 hours, then continue to be warming up to 80-95 DEG C, react after 5-15 hour and stop heating, keep being stirred to temperature and reduce to room temperature, then continuing progressively raised temperature, steam pore-creating agent, obtaining resin intermediate through washing also drying;
4) above-mentioned resin intermediate is proceeded in reactor, after heated inert swelling agent is fully swelling, add the lewis acid catalyst of 10-30% resin intermediate quality, be warming up to 75-125 DEG C, react after 2-15 hour and stop heating, keep being stirred to temperature and drop to room temperature, then progressively raised temperature is continued, steam swelling agent, washing resin is also dried, and obtains containing ester group adsorbent resin with high specific surface area.
2. one according to claim 1 is containing ester group adsorbent resin with high specific surface area, and it is characterized in that the particle diameter of resin is 0.3-0.85mm, water ratio is 55-65%, and specific surface area is greater than 600m
2/ g.
3. one according to claim 1 is containing ester group adsorbent resin with high specific surface area, it is characterized in that step 1) described in dispersion agent be one or both mixture in gelatin, polyvinyl alcohol, methylcellulose gum, Natvosol or methylhydroxypropylcellulose.
4. one according to claim 3 is containing ester group adsorbent resin with high specific surface area, it is characterized in that step 2) described in ester group linking agent be one or both mixture in diethyleneglycol dimethacrylate(DEGDMA), allyl methacrylate(AMA), cyamelide allyl ester or allyl itaconates; Step 2) in pore-creating agent be one in isopropylcarbinol, primary isoamyl alcohol, toluene, dimethylbenzene, enanthol or hexalin; Step 2) in conditioning agent be the mixture of one or more in diethylene glycol dimethyl ether, pentan-thiol, toluene dichloride, divinylbenzene, 2,2-two (allyloxymethyl)-butane-1 alcohol or oleic acid; Step 2) in initiator be one or both mixture in benzoyl peroxide, Diisopropyl azodicarboxylate or azo-bis-iso-dimethyl.
5. one according to claim 4 is containing ester group adsorbent resin with high specific surface area, it is characterized in that step 4) described in inertia swelling agent be one in tetracol phenixin, zellon, oil of mirbane, 1,2-ethylene dichloride or sym.-tetrachloroethane; Step 4) in lewis acid catalyst be one in aluminum chloride, zinc dichloride, tin tetrachloride, Indium-111 chloride, iron trichloride or trimethylchlorosilane.
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| CN104826615A (en) * | 2015-04-30 | 2015-08-12 | 衡水利得绿色生物科技有限公司 | Adsorption resin for crystallization of stevioside |
| CN107376874A (en) * | 2017-08-18 | 2017-11-24 | 江苏海普功能材料有限公司 | Heavy metal absorbent and preparation method thereof |
| CN114671970B (en) * | 2022-03-29 | 2023-10-27 | 中国科学院广州能源研究所 | Method for removing sugarcane molasses pigment by using ultra-high crosslinking adsorption resin |
| CN118580405B (en) * | 2024-08-06 | 2024-10-11 | 江苏金杉新材料有限公司 | Adsorption resin with porous structure and preparation method thereof |
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