CN102827366A - Polymeric adsorbent for removing formaldehyde and preparation method thereof - Google Patents
Polymeric adsorbent for removing formaldehyde and preparation method thereof Download PDFInfo
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- CN102827366A CN102827366A CN2012102535191A CN201210253519A CN102827366A CN 102827366 A CN102827366 A CN 102827366A CN 2012102535191 A CN2012102535191 A CN 2012102535191A CN 201210253519 A CN201210253519 A CN 201210253519A CN 102827366 A CN102827366 A CN 102827366A
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Abstract
The invention discloses a polymeric adsorbent for removing formaldehyde and a preparation method and applications of the polymeric adsorbent. The preparation method is to prepare the cross-linked melamine resin based on the property of the melamine that primaquine is contained and the periodic acid Schiff reaction can be carried out with the formaldehyde. The polymeric adsorbent is uniform in structure and is capable of achieving the purpose of absorbing the formaldehyde with a high adsorption quantity by absorbing through a hydrogen bond, enriching formaldehyde molecules, and carrying out the periodic acid Schiff reaction with the formaldehyde. The polymeric adsorbent has high absorption quantity of the formaldehyde, and is not needed to be regenerated frequently, so that the total cost is low. The polymeric adsorbent for absorbing the formaldehyde is beneficial for treating the pollution of the formaldehyde in a room and purifying the wastewater with formaldehyde contained. The polymeric adsorbent for removing the formaldehyde has the chemical structure shown as follows.
Description
Technical field
The present invention relates to a kind of crosslinked trimeric cyanamide polymeric adsorbent and preparation method and application.
Background technology
Formaldehyde is a kind of irritant gas, mainly stimulates respiratory tract, causes abnormal pulmonary function, and long-term contact can cause pulmonary emphysema, cancer etc.On " the carcinogenic communique " of issue in 2004, formaldehyde is listed in " clear and definite carcinogenic " material in IARC (iARC).The smell of formaldehyde is also little, and is limited to olfactory stimulation.When people came into the firm room of fitting up, the sharp aroma that smells mainly was the smell of isocyanic ester, free ammonia, benzene class etc., and the taste of formaldehyde has been covered by these smells, generally can't smell.
Indoor formaldehyde is mainly derived from the used artificial board of finishing.The sizing agent that artificial board is commonly used is urea-formaldehyde resin, resol and melamine formaldehyde resin.After fitting up end, these resins can slowly be degraded and long release formaldehyde.Research shows that the release period of formaldehyde generally can reach 3-15 in the wood-based plate.In addition, coating, paint, putty tackiness agent, plastic cement carpet, chemical fibre dress material etc. also are the important sources of indoor formaldehyde.
Along with interior decoration popularize the increase with the airtight degree in room day by day, formaldehyde pollutes more and more serious.According to environmental administration's statistics, in 1-6 month, the formaldehyde exceeding standard rate in the room reaches 80% after the house decoration, and meeting room and office are near l00%; Fitting up the house that concentration of formaldehyde exceeds standard after 3 years still reaches more than 50%.
Seriously polluted the healthy of people that influence of formaldehyde, countries in the world are all paid special attention to this.Developed country has just proposed the notion of " the buildings syndromes of causing a disease " in the seventies in 20th century, and from then on people begin to note and study pathogenesis and the control measures that indoor formaldehyde pollutes.World major country has all issued the rules that indoor formaldehyde concentration is limited the quantity of, and concentration of formaldehyde can not surpass prescribed value in the room after requiring to fit up.
Because present domestic popular is decoration and the very different present situation of finishing material excessively, causes the room air pollution situation very serious.Formaldehyde improvement method commonly used at present mainly is physisorphtion and chemiadsorption, introduces respectively below:
The physisorphtion physical adsorption mainly relies on intermolecular forces to work, and belongs to reversible adsorption.Present physical absorbent on the market mainly is the gac of vesicular structure.It belongs to non-polar adsorbent, and non-polar compound and low-pole compound are had adsorption effect preferably, and relatively poor to strong polar formaldehyde adsorption effect.People such as the Dong Chunxin of Northeast Normal University discover that the acticarbon of selling on the market promptly reaches absorption about 5 hours saturated, lose the ability of further absorbing formaldehyde, and this indoor formaldehyde to slow release does not have the effect of radical cure.People attempt to increase the polarity of activated carbon surface through with strong acid, strong oxidizer etc. gac being carried out surface-treated, improve adsorption effect.The adsorptive power of the gac after the modification increases, but the improvement that is used for indoor formaldehyde also is nowhere near, and is further improved.
For example, publication number is that the patent of CN101549281A discloses a kind of method of improving NACF PARA FORMALDEHYDE PRILLS(91,95) absorption property, and it is to utilize low-temperature plasma that NACF is carried out surface-treated.This method has improved running cost, and is limited but the adsorption rate of PARA FORMALDEHYDE PRILLS(91,95) improves.
Chemiadsorption domestic chemosorbent at present mainly is divided into two types:
(1) the coating type formaldehyde adsorbent it be that formaldehyde adsorbent is added in the coating, spread upon on the room wall then.The addition of polyamine is considerably less in this type coating, this be since polyamine can be in air gradually oxidation become dark matter, influence the finishing effect in room, so can not heavy addition.Therefore, this type coating only has adsorption effect to formaldehyde in the newly-decorated room; After the some months, along with after the adsorptive capacity of polyamine reaches capacity, indoor formaldehyde concentration will rise to a high position again.Here it is why the formaldehyde adsorbent of coating type had only the reason of some months effective period of indoor formaldehyde concentration.
For example: publication number is that this coating of patent of CN102391741A comprises citrus peel extract, emulsion, white titanium pigment etc. and adds in the coating, is used for absorbing formaldehyde, after formaldehyde absorption is saturated, promptly ceases to be in force automatically, and can not regenerate or change.
(2) it is to be sprayed onto in the room with the liquid absorbent that contains primary amine to spray the removing method, comes the temporary transient indoor formaldehyde of removing.This type sorbent material can reduce indoor formaldehyde concentration fast, but it is shorter to adsorb validity period, has often just lost efficacy after several days.Because the formaldehyde in the room slowly releases, this just needs long continuous several times to spray could really reach the removing effect.
To the problem of indoor formaldehyde concentration superelevation, it is big to develop adsorptive capacity, is difficult for losing efficacy, and the product of ability life-time service reaches the ideal regulation effect.
Summary of the invention
The purpose of this invention is to provide a kind of polymeric adsorbent of removing formaldehyde,, satisfy people's demand to overcome the above-mentioned defective that prior art exists.
The polymeric adsorbent of removing formaldehyde of the present invention is the three-dimensional netted macromole that is formed by melamine molecule and linking agent coupling, outward appearance structure spherical in shape, and the primary amine group that wherein comprises is a major function group of removing formaldehyde, its chemical structure fragment is following:
Preparing method of the present invention comprises the following steps:
(1) trimeric cyanamide, 0.5～5 parts by weight of cross-linking agent of 1 weight part are mixed with the additive of 0～1 weight part; Disperse at 10～70 ℃ of following supersound process 0.5～5h; Preferably, obtain the soup compound that trimeric cyanamide mixes at 20～40 ℃ of following supersound process 0.5～2h;
Described linking agent is selected from more than one in Tetra hydro Phthalic anhydride, phthalyl chloride, Succinic anhydried, chloro-acetyl chloride, oxyethane, epoxy chloropropane, formaldehyde, suceinic aldehyde, succinic chloride or the poly acryloyl chloride;
Described additive is selected from more than one of triethylene tetramine, TEPA, urea, guanidine, glycerine or tetramethylolmethane;
The parts by weight of component are:
1 part of trimeric cyanamide, 0.5～5 part of linking agent, 0～1 part of additive;
Preferably:
Trimeric cyanamide is 1 part, and linking agent is 0.5～3 part, 0～1 part of additive;
(2) soup compound is reacted 2～50h at 20～100 ℃, obtain the underflow of precrosslink;
Preferably, at 40～60 ℃ of reaction 1.5～4h;
(3) underflow with precrosslink is distributed in the oil phase, and 0～100 ℃ of reaction 2～30h collects gel resin pearl wherein then; Preferably, at 70～100 ℃ of reaction 6～14h;
Said oil phase is made up of organic solvent and suspension dispersive agent;
Weight ratio is: organic solvent: suspension dispersive agent=100: 1.2～2.5;
Organic solvent is selected from dichlorobenzene, hexanaphthene, octane or oil of mirbane etc.;
Suspension dispersive agent is selected from linear polystyrene, SE or linear TEB 3K;
Or suspension dispersive agent is selected from the multipolymer of linear polystyrene, SE and linear TEB 3K;
Floating dispersion agent is selected from the blend of linear polystyrene, SE and linear TEB 3K;
(4) with the described gel resin pearl of the 1 weight part resin column of packing into, carry out wash-out with the eluent of 5-30 weight part, it is resin dedicated to obtain absorbing formaldehyde.
Described eluent is the aqueous solution of yellow soda ash, sodium hydroxide or ammonia etc., and weight concentration is 3～15%;
The resin bead that the present invention obtains is yellow or brown beadlet, and smooth in appearance is stable to the formaldehyde adsorptive capacity in the aqueous solution, surpasses 130mg/g.
The absorbing formaldehyde resin that the present invention obtains can be applied to absorption of formaldehyde in the purification, air of formaldehyde-containing wastewater etc.
Absorbing formaldehyde disclosed by the invention is resin dedicated, is to be the condensation polymer type polyamines resin of raw material with the trimeric cyanamide.Trimeric cyanamide once was added in the interior wall coating, used as the indoor formaldehyde scavenging agent; But because trimeric cyanamide solubleness in water soluble paint is little, cause addition limited, a large amount of formaldehyde between being difficult to new clothes are repaired the house are effectively removed.This is that the present invention uses the polycondensation method to be made into the reason that resin particle uses.
The present invention is that the utilization trimeric cyanamide contains uncle's ammonia, has the characteristic of carrying out schiff's reaction with formaldehyde, prepares crosslinked melamine resin.Its even structure, itself can pass through adsorption by hydrogen bond, and the enrichment formaldehyde molecule through carrying out schiff's reaction with formaldehyde, reaches the purpose of the absorbing formaldehyde of high adsorption capacity then.
Evidence, the present invention can effectively solve the evil of present indoor formaldehyde pollution, is beneficial to the health that ensures huge numbers of families, has bigger benefit for office work personnel and pregnant woman, children, and remarkable social benefit and environmental benefit are arranged.
The present invention is a kind of trimeric cyanamide condensation-type adsorbent resin of high functional group content, and the formaldehyde adsorptive capacity is high, does not need frequent regeneration, and overall cost is low.Use absorbing formaldehyde resin of the present invention, help to carry out the improvement of the formaldehyde pollution in the room and the purification of formaldehyde-containing wastewater.
Description of drawings
Fig. 1 is the infared spectrum of the product of embodiment 1 acquisition.
Fig. 2 is the electromicroscopic photograph of the product of embodiment 1 acquisition.
Embodiment
Following embodiment further specifies of the present invention, rather than limits scope of the present invention.
A. trimeric cyanamide 21g mixes with the poly acryloyl chloride (about molecular weight 1000) of 33g, is controlled at 20 ℃ of following supersound process 0.5 hour, the soup compound that obtains mixing;
B. with above-mentioned soup compound 60 ℃ of reaction 3h under agitation, obtain the underflow of precrosslink;
C. the linear polystyrene with 200mL orthodichlorobenzene, 120mL YLENE, 12g molecular weight 50,000 mixes as oil phase; With the underflow 30g of the precrosslink that obtains in the step (b), add oil phase and mix 90 ℃ of controlled polymerization temperature; Stirring reaction 8 hours; Suction filtration also soaks with methyl alcohol, uses water washing then, obtains gel resin pearl 43g;
D. measure the gel resin pearl 20g that obtains in the step (c) pack into ion exchange column, with the aqueous hydrochloric acid wash-out of 500 gram 0.5mol/L, and then water is washed till near neutral, obtains the resin bead 17g that PARA FORMALDEHYDE PRILLS(91,95) has special adsorptive power.This resin outward appearance is light color or reddish-brown globosity; Diameter 0.3-1.2mm; Water cut is 50%, can be under neutrality or alkaline condition formaldehyde and other small molecule aldehydes in absorbed air and the aqueous solution, and under acidic conditions, can the aldehydes that adsorb be discharged; Again carry out next round absorption then, reach reusable effect.
Infared spectrum such as Fig. 1.
Embodiment 2
A. trimeric cyanamide 28g mixes with TEPA 12g, Tetra hydro Phthalic anhydride 65g, spends following supersound process 0.5 hour, the soup compound that obtains mixing 20;
B. the soup compound with above-mentioned processing is controlled at 40 ℃ of left and right sides stirring reaction 4h, obtains the underflow of precrosslink;
Step (c) changes 70 ℃ of controlled polymerization temperature into, stirring reaction 14 hours.
Step (d) is with embodiment 1.
Embodiment 3
Step b, c, d are with embodiment 2; Step a changes the triethylene tetramine with trimeric cyanamide 30g and 10g into, and linking agent is the LUTARALDEHYDE of 40g, adds 50mLN simultaneously, and dinethylformamide is a solvent, and other is with embodiment 2.
Embodiment 4
Trimeric cyanamide mixes with TEPA, uses suceinic aldehyde precrosslink then, at 70 ℃ of reversed-phase polymerizations, uses the sodium chloride aqueous solution wash-out then.
Step b, c, d are with embodiment 2; Step a changes into: trimeric cyanamide 28g is mixed with suceinic aldehyde 35g with TEPA tetraethylene pentamine 8g, obtain composite mixture after ultrasonic.
Embodiment 5
Step b, c, d are with embodiment 2; The trimeric cyanamide that step a changes into 30g mixes with the urea of 15g, and at room temperature supersound process is 0.5 hour, adds weight concentration then and be 37% formalin 36 grams, then supersound process 20 minutes at room temperature.
Embodiment 6
Step a, b, d are with embodiment 2; Step c changes into: the linear TEB 3K of 200mL orthodichlorobenzene, 140mL sherwood oil, 14g molecular weight 20,000 is mixed, fully stir, as oil phase.With the underflow 30g of the precrosslink that obtains among the step b, mix with the oil phase for preparing in advance then, 60 ℃ of controlled polymerization temperature, stirring reaction 14 hours, suction filtration and washing obtain gel resin pearl 85g.
Embodiment 7
Step b, c are with embodiment 6; Step a changes into: trimeric cyanamide 28g is mixed with Succinic anhydried 27g, and ultra-sonic dispersion 0.5 hour obtains reaction mixture; Steps d changes into: measure the gel resin pearl 20g that obtains among the step c pack into ion exchange column, with 130 grams, 95% alcohol immersion three hours, wash-out then, next reusable heat washing obtains the resin bead 17g that PARA FORMALDEHYDE PRILLS(91,95) has special adsorptive power.
Embodiment 8
Step b, d are with embodiment 6; Step a changes into: trimeric cyanamide 28g mixed with tetramethylolmethane 9g, adds poly acryloyl chloride 38g then, and ultra-sonic dispersion 0.5 hour, 60 ℃ of reaction 1.5h obtain lightly crosslinked underflow then; Step c changes into: the linear polystyrene of 100mL orthodichlorobenzene, 100mL ethylbenzene, 6g molecular weight 50,000 is mixed, fully stir, as oil phase.Measure the lightly crosslinked underflow 30g that obtains among the step b, mix with the oil phase for preparing in advance, 80 ℃ of controlled polymerization temperature, stirring reaction 8 hours, 100 ℃ were reacted 2 hours then, and suction filtration and washing obtain gel resin pearl 25g.
Embodiment 9
Trimeric cyanamide is mixed with glycerine, use poly acryloyl chloride precrosslink then, it uses the sodium chloride aqueous solution wash-out then at the high temperature reversed-phase polymerization.
Step b, c, d are with embodiment 8; Step a changes into: with trimeric cyanamide and the 8g glycerine mixed of 28g, use poly acryloyl chloride 40g precrosslink then, at room temperature 0.5 hour membrane filtration of supersound process obtains premixed soup compound.
Embodiment 10
Step b, c, d are with embodiment 8; Step a changes into: the trimeric cyanamide of 28g is mixed with the polyethylene polyamine of 10g, add poly acryloyl chloride 75g then, at room temperature supersound process is 0.5 hour, and membrane filtration obtains prepolymerized soup compound.
Embodiment 11
Trimeric cyanamide mixes with polyethylene polyamine, then with epoxy chloropropane in advance and succinic chloride as mixed cross-linker, 40 ℃ of reversed-phase polymerizations then.
Step b, d are with embodiment 10; A changes into step: the trimeric cyanamide of 28g is mixed with the polyethylene polyamine of 10g, add poly acryloyl chloride 55g then, after ultrasonic 20 minutes of the normal temperature of control, add succinic chloride 28g, continued then ultrasonic 10 minutes.Step c changes into: the linear polystyrene of 200mL orthodichlorobenzene, 150mL hexanaphthene, 10g molecular weight 50,000 is mixed, fully stir, as oil phase.With the lightly crosslinked underflow 30g that obtains among the step b, mix with the oil phase for preparing in advance, 100 ℃ of controlled polymerization temperature, stirring reaction 6 hours, suction filtration and washing obtain gel resin pearl 26g.
Embodiment 12
Step a, b, d are with embodiment 10; Step c changes into: the linear polystyrene of 100mL orthodichlorobenzene, 120mL sherwood oil, 2g molecular weight 50,000, the linear TEB 3K of 2g molecular weight 20,000 are mixed, fully stir, as oil phase.With the lightly crosslinked underflow 30g that obtains among the step b, mix with the oil phase for preparing in advance, 80 ℃ of controlled polymerization temperature, stirring reaction 12 hours, suction filtration and washing obtain gel resin pearl 21g.
Embodiment 13
Step b, c, d are with embodiment 12; Step a changes into: trimeric cyanamide 28g is mixed with Tetra hydro Phthalic anhydride 15g and succinic chloride 14g, and ultra-sonic dispersion 0.5 hour obtains reaction mixture.
Embodiment 14
Adopt the method for the indoor quality air standard code of GB GB/T18883-2002, the performance of the absorbing formaldehyde of the product of embodiment 1～13 is detected, be converted into the adsorptive capacity that every gram is removed resin, the result is following:
Table 1 resin sample is to the s-adsorption of formaldehyde in the air
Claims (9)
1. remove the polymeric adsorbent of formaldehyde, it is characterized in that the chemical structure fragment is following:
2. the preparation method of the polymeric adsorbent of removing formaldehyde according to claim 1 is characterized in that, comprises the following steps:
(1) with trimeric cyanamide, linking agent and additive blending dispersion, obtains the soup compound that trimeric cyanamide mixes;
Described linking agent is selected from more than one in Tetra hydro Phthalic anhydride, phthalyl chloride, Succinic anhydried, chloro-acetyl chloride, oxyethane, epoxy chloropropane, formaldehyde, suceinic aldehyde, succinic chloride or the acrylate chloride;
Described additive is selected from more than one of triethylene tetramine, TEPA, urea, guanidine, glycerine or tetramethylolmethane;
(2) soup compound is reacted h, obtain the underflow of precrosslink;
(3) underflow with precrosslink is distributed in the oil phase, and gel resin pearl is wherein collected in reaction then;
(4) with the described gel resin pearl resin column of packing into, carry out wash-out with eluent, it is resin dedicated to obtain absorbing formaldehyde.
3. method according to claim 2 is characterized in that, in the step (1), the weight of each component is: trimeric cyanamide 1 weight part, linking agent 0.5～5 weight part, additive 0～1 weight part.
4. method according to claim 2 is characterized in that, in the step (2), soup compound at 20～100 ℃ of reaction 2～50h, is obtained the underflow of precrosslink.
5. method according to claim 2 is characterized in that, in the step (3), the underflow of precrosslink is distributed in the oil phase 0～100 ℃ of reaction 2～30h.
6. method according to claim 5 is characterized in that said oil phase is made up of organic solvent and suspension dispersive agent; Weight ratio is: organic solvent: suspension dispersive agent=100: 1.2～2.5;
Organic solvent is selected from dichlorobenzene, hexanaphthene, octane or oil of mirbane;
Suspension dispersive agent is selected from linear polystyrene, SE or linear TEB 3K;
Or suspension dispersive agent is selected from the multipolymer of linear polystyrene, SE and linear TEB 3K;
Or suspension dispersive agent is selected from the blend of linear polystyrene, SE and linear TEB 3K.
7. according to the described method of claim 2, it is characterized in that described eluent is the aqueous solution of yellow soda ash, sodium hydroxide or ammonia, weight concentration is 3～15%.
8. according to the described method of claim 7, it is characterized in that,, carry out wash-out with the eluent of 5-30 weight part with the described gel resin pearl of the 1 weight part resin column of packing into.
9. the application of the polymeric adsorbent of removing formaldehyde according to claim 1 is characterized in that, is used for the purification of formaldehyde-containing wastewater, the absorption of air formaldehyde.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104762041A (en) * | 2015-03-26 | 2015-07-08 | 北京林业大学 | Modified urea resin adhesive and preparation method thereof |
| CN105413658A (en) * | 2015-12-09 | 2016-03-23 | 广东南海普锐斯科技有限公司 | Formaldehyde purification porous adsorption film and preparation method thereof |
| CN111234291A (en) * | 2020-03-06 | 2020-06-05 | 郑州峰泰纳米材料有限公司 | Preparation method of melamine formaldehyde resin flame-retardant foam |
| CN115304760A (en) * | 2022-07-21 | 2022-11-08 | 中南大学 | Polyamine-formaldehyde adsorption material and preparation and application thereof |
| CN115722276A (en) * | 2022-11-15 | 2023-03-03 | 江苏美亚科泽过滤技术有限公司 | Granular multi-effect adsorbent composition and preparation method thereof |
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| CN115304760A (en) * | 2022-07-21 | 2022-11-08 | 中南大学 | Polyamine-formaldehyde adsorption material and preparation and application thereof |
| CN115304760B (en) * | 2022-07-21 | 2023-09-26 | 中南大学 | Polyamine formaldehyde adsorption material and preparation and application thereof |
| CN115722276A (en) * | 2022-11-15 | 2023-03-03 | 江苏美亚科泽过滤技术有限公司 | Granular multi-effect adsorbent composition and preparation method thereof |
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Application publication date: 20121219 |