CN102553546B - High-molecule adsorption material - Google Patents
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Abstract
The invention relates to a high-molecule adsorption material, which is a polymer with a novel resin structure and is greatly different from the conventional phenylethylene crosslinked high-molecule adsorption resin. A main body structure of the high-molecule adsorption material is a network structural system consisting of an aromatic benzene ring and a methylene structure which are connected with each other. A preparation method comprises the following steps of: performing continuous pay-gram alkylation polymerization reaction on a derivative such as benzene-type aromatic hydrocarbon and the like and a precursor dichlorine methyl-type rigid cross-linking agent; and synthesizing a novel non-combustible adsorption material and non-phenylethylene type adsorption resin material. The material is high in polymerization reaction yield, and can be applied to fields of air purification, such as leakage treatment for dangerous chemical substances, adsorption and elimination of industrial poisonous and harmful substances, treatment for tail gas from a factory, effective and quick absorption and removal of oil pollution on a water surface and the like, research and development on relevant protection materials of personal safety protection devices and the like.
Description
Technical field
The present invention relates to a kind of preparation of polymer adsorbing material, and evaluation and the using method of using this sorbing material to purify to be subject to hazardous chemical (comprising: hazardous contaminant in air, poisonous and harmful industrial chemical TICs as benzene etc.) contaminated surface.
Background technology
The leakage of the hazardous chemical (as: agricultural chemicals and poisonous and harmful industrial chemical TICs etc.) causing due to reasons such as burst natural calamity, contingencies has in recent years become one of significant threat of public safety; In addition, terrorist's activity is in recent years increasing, and they may utilize hazardous chemical (as: poisonous and harmful industrial chemical TICs etc.) to implement surprise attack for dense population region.For the area people that is contaminted, place and object, carry out purified treatment fast and efficiently, become the most important means of support personnel's safety under above-mentioned form.Wherein, the jumbo sorbing material of high-ratio surface is effectively to carry out the critical material that contaminants associated purification removes, and is also the critical material of widely applying in the separated material of main part of post, has very important economic worth and realistic meaning.
Conventional sorbing material generally has active carbon, molecular sieve, silica gel and zeolite etc., wherein, active carbon is because of its flourishing pore structure and higher adsorption capacity, become that purposes is the widest, the maximum adsorbent of consumption, in the occupational protection equipment of China, also used and take the Pd/carbon catalyst that active carbon is carrier.But, due to the characteristic of material with carbon element self, there is inflammable and heat-proof quality, and adsorption process being an exothermic process, the heat of adsorption discharging in adsorption process is constantly accumulated, and may cause active carbon layer temperature to raise and locate combustion.General common active carbon autoignition temperature, between 300 ℃-450 ℃, has been added the active carbon autoignition temperature of catalyst and may be down between 150 ℃-300 ℃.In the high humidity environment using at protective equipment, active carbon can significantly reduce the adsorption capacity to pernicious gas because of adsorbed water, thereby significantly reduces the integrated protection performance of relevant equipment.Therefore, how to guarantee that under the prerequisite of protective materials correlative protection performance, exploring the nonflammable sorbing material of novel non-carbon has become a difficult problem in the urgent need to address in protective materials development process.
The beginning of this century, the U.S. starts to pay close attention to porous polymer resin material, and this is because porous polymer resin shows many excellent specific properties.Resin material functionalization technical maturity, is easy to carry out functionalization by grafting, modification, as realizes catalysis and anti-flaming function.Superhigh cross-linking resin has good hydrophobic performance, in storage and application process, can not lose efficacy because of the moisture in absorbed air, and in the process of desorption and regeneration, after use water vapour desorption, sorbing material can not contain a large amount of water does not need to dry and again adsorb and use.Although reported for work several several non-carbon adsorbing materials with high specific surface area at present abroad, various metals organic backbone (MOFs) material of preparing as people such as Matzger A.J., covalent bond organic backbone (COFs) material, conjugation capillary copolymer material (CMPs) etc., these materials all have that specific area is high (can be reached>=2000m
2/ g) and abundant microcellular structure, they are also very active in the perspective study in the fields such as the target release of hydrogen storage material, pharmaceutical carrier and medicine, electrode film material.But in general,, this class material raw materials used expensive (needing high purity reagent), synthesis condition harsh (needing anhydrous and oxygen-free operation), at present also in the laboratory early-stage Study stage, be also difficult to realize for the moment suitability for industrialized production more.
Compared with the above case, macroreticular resin and the equal hole of large net superhigh cross-linking resin, its technology of preparing and more ripe in the application of different field.The common pore-size distribution of macroreticular resin wide (containing big or middle, micropore), homeo-osmosis are poor, exist adsorptive selectivity low and in using or regenerating breakable shortcoming.And net greatly equal hole superhigh cross-linking resin, at aspects such as microcellular structures, than macroreticular resin, there is obvious improvement, but its preparation is more loaded down with trivial details, need be through the polymerization in advance of the monomers such as styrene, then the multistep reaction preparations such as additive-crosslinking under solution or height swelling, only have a kind of structure type of styrene at present.Traditional phenylethylene Linear Polymer and the general configuration of cross-linked adsorbing resin are as follows respectively:
Such polymeric adsorbent specific area is difficult to surpass 1000m
2/ g, widens its large-scale industry preparation and application and is subject to certain limitation.2002, founder professor Davankov of superhigh cross-linking resin once foretold: " up to the present, to be still superhigh cross-linking resin first be also unique representative to styrene type structure.But there is no doubt that: other many macromolecule resins, if its network structure has with like polystyrene superhigh cross-linking network class, form principle, also may have with polystyrene type superhigh cross-linking resin-phase like property ".But on document, yet there are no up to now, the report of relevant high-ratio surface preparation.
Summary of the invention
The present invention relates to the nonflammable polymer adsorbing material of a kind of novel non-styrene high-ratio surface, and the preparation method of this macromolecular material is provided and to hazardous contaminant simulant dimethoxy-methyl phosphate (DMMP), poisonous and harmful chemicals in air as absorption properties such as benzene.Meanwhile, also introduced evaluation or the using method of using this sorbing material absorption to remove to be subject to hazardous chemical (comprising: hazardous contaminant in air, poisonous and harmful industrial chemical as benzene etc.) contaminated surface.This nonflammable polymer adsorbing material, has verified the prophesy that above-mentioned Davankov teaches, and material specific area can reach 1300m
2more than/g, and there is the many merits such as pore-size distribution narrow (substantially concentrate on micropore and low side is mesoporous), and raw materials used cheap and easy to get, and technique is simple, is easy to large-scale industry preparation, has important theory and realistic meaning.
The agent structure of the nonflammable polymer adsorbing material of novel high-ratio surface in the present invention is the network struture system that fragrant phenyl ring and methylene structure are formed by connecting, by the arene derivatives such as benzene and precursor chloromethane base class rigidity crosslinking agent, continuous pay-Ke alkylated reaction occurs and form, chemical equation is as follows:
X in formula, y are 1～6.
This polymerisation is the pay-Ke alkylated reaction of a quasi-representative, normally the arene derivatives such as toluene, benzene is reacted at 20～200 ℃ with precursor dichloride methyl class crosslinking agent, with higher reaction yield, obtains resin product.Pore Characterization and Study on adsorption properties that such novel nonflammable sorbing material is carried out show: this type of material not only specific area is 1300m
2more than/g, and it is narrow to have pore-size distribution, substantially concentrates on micropore and low side is mesoporous, and aromatic hydrocarbons organic molecule is had to very high absorption property, and adsorption capacity is more than 400mg/g.
Typical preparation method is according to the mol ratio of metering (toluene or benzene: precursor dichloride methyl class rigidity crosslinking agent=1:1～20) evenly mix in solvent by two reactants, the arene derivatives such as toluene used, benzene can be phenmethylol, methyl phenyl ethers anisole, diphenyl ether, toluene, benzene, biphenyl, naphthalene etc., and chloromethane base class arene derivatives can be for dichloride methyl benzene, chloromethylbenzene, to chloromethyl methoxybenzene, dichloride methyl biphenyl, chloromethyl biphenyl, chloromethyl naphthalene, chloromethylbenzene methyl alcohol, xylylene dichlorides, dichloromethyl biphenyl etc.One or more for solvent in chlorobenzene, o-dichlorohenzene, carrene, chloroform, carbon tetrachloride, monochlorethane, dichloroethanes, trichloroethanes, dichloro-propane, cyclohexane or nitrobenzene etc.The catalyst adding is one or more in titanium tetrachloride, five vanadium chlorides, zinc chloride, zinc bromide, zinc acetate, trifluoroacetic acid zinc, alchlor, three fluosulfonic acid zinc, alchlor, three fluosulfonic acid aluminium, stannous chloride, butter of tin, anhydrous ferric trichloride, anhydrous ferric bromide, three fluosulfonic acid iron, boron trifluoride, boron chloride, Boron tribromide, perfluor triphenyl borine etc., and at 20～200 ℃, nitrogen protection reaction is 3～144 hours.After reaction finishes, be cooled to room temperature, filter, respectively with washing 1-48 hour such as the sulfuric acid solution of benzinum, a small amount of ether, a large amount of running water, dilution, distilled water, acetone, then at 40-180 ℃ vacuum drying 3-72 hour final products.
The pore structure of this material uniqueness and higher specific surface thereof are expected to be applied to contamination personnel, place and object and carry out purified treatment fast and efficiently, plant tail gas purifies, effective fast enriching of water oil stain is absorbed, in the fields such as research and development of the correlative protection materials such as air in closed space purification.
Accompanying drawing explanation
The N of Fig. 1 macromolecule resin
2adsorption-desorption curve (A-absorption, D-desorption), abscissa: relative pressure, ordinate: adsorbance.
The graph of pore diameter distribution of Fig. 2 macromolecule resin, abscissa: aperture, ordinate: differential pore volume.
The INFRARED ABSORPTION of Fig. 3 macromolecule resin material (FT-IR) figure, abscissa: temperature, ordinate: percent weight loss.
The aerial TG-DTA figure of Fig. 4 macromolecule resin material, abscissa: temperature, ordinate: percent weight loss.
The dynamic phenenyl absorbing amount temporal evolution of Fig. 5 macromolecule resin sample figure, abscissa: adsorption time, ordinate: phenenyl absorbing amount percentage.
The static DMMP adsorbance temporal evolution figure of Fig. 6 macromolecule resin sample, abscissa: adsorption time, ordinate: adsorbance percentage.
The specific embodiment
Hazardous chemical involved in the present invention, high malicious chemicals etc. are all equal to if no special instructions, not only comprise hazardous contaminant in air, also comprise poisonous industrial chemical.The nonflammable polymer adsorbing material of high-ratio surface provided by the invention, belong to a kind of superhigh cross-linking resin, there is good hydrophobic performance, in storage and application process, can not lose efficacy because of the moisture in absorbed air, and in the process of desorption and regeneration, after use water vapour desorption, sorbing material can not contain a large amount of water does not need to dry and again adsorb and use.This material can be rapidly remove hazardous chemical absorption, if by its with disinfectant powder as mixed uses in certain proportion such as atlapulgites, be expected obviously to improve the clear up performance of existing product to hazardous contaminant in air and hazard chemicals.
The preparation of the nonflammable polymer adsorbing material of high-ratio surface
Two reactants are added in the there-necked flask of 250ml according to the mol ratio (1mmol benzene and 1mmol chloromethylbenzene) of metering; add after the abundant swelling of 120ml nitrobenzene; the Using Aluminium Trichloride as Catalyst reaction that adds 0.2mmol; nitrogen protection reaction 3h at 40 ℃ of temperature, then react 12h under the temperature 60 C that raises.After reaction finishes, be cooled to room temperature, filter, respectively with washings such as a small amount of benzinum, a large amount of running water, 0.5mol/L hydrochloric acid solutions repeatedly, using again apparatus,Soxhlet's with acetone as the extractant cleaning product that refluxes, finally by 100 ℃ of vacuum drying 48 hours final products.
Two reactants are added in the there-necked flask of 500ml according to the mol ratio (1mmol toluene and 5mmol dichloride methyl biphenyl) of metering; add after the abundant swelling of 200m1 trichloroethanes; the trifluoroacetic acid zinc catalytic reaction that adds ferric trichloride and the 0.1mmol of 0.2mmol; nitrogen protection reaction 6h at 60 ℃ of temperature, then react 24h at 80 ℃ of the temperature of raising.After reaction finishes, be cooled to room temperature, filter, respectively with washings such as a small amount of benzinum, a large amount of running water, 0.5mol/L hydrochloric acid solutions repeatedly, using again apparatus,Soxhlet's with acetone as the extractant cleaning product that refluxes, finally by 120 ℃ of vacuum drying 24 hours final products.
Embodiment 3
Two reactants are added in the there-necked flask of 500ml according to the mol ratio (1mmol benzene and 8mmol chloromethylbenzene) of metering; add after 120ml nitrobenzene, 100ml chlorobenzene and the abundant swelling of 30ml cyclohexane; the three fluosulfonic acid iron, the boron chloride of 0.1mmol and the reaction of the stannic chloride catalysis of 0.1mmol that add 0.2mmol; nitrogen protection reaction 2h at 5 ℃ of temperature, then react 48h at 100 ℃ of the temperature of raising.After reaction finishes, be cooled to room temperature, filter, respectively with washings such as a small amount of benzinum, a large amount of running water, 0.5mol/L hydrochloric acid solutions repeatedly, using again apparatus,Soxhlet's with acetone as the extractant cleaning product that refluxes, finally by 160 ℃ of vacuum drying 48 hours final products.
The above-mentioned description to embodiment is can understand and apply the invention for the ease of those skilled in the art.Person skilled in the art obviously can easily make various modifications to these embodiment, and General Principle described herein is applied in other embodiment and needn't passes through performing creative labour.Therefore, the invention is not restricted to the embodiment here, those skilled in the art are according to announcement of the present invention, and the improvement of making for the present invention and modification all should be within protection scope of the present invention.
Fig. 1 has provided the N of macromolecule resin
2adsorption-desorption curve (A-absorption, D-desorption).By calculating the specific surface of the nonflammable sorbing material of this macromolecule, be 1391m
2/ g, pore-size distribution is narrow, and substantially concentrates on micropore and the mesoporous region of low side, as shown in Figure 2.Fig. 3 is the aerial thermogravimetric one differential thermal figure of macromolecule resin material, while testing, since about the 220 ℃ absorption that first an oxygen occur (reaction to a certain degree also may occur) process, to 340 ℃ of maximum weightening finishes of left and right sample, reach 10.28% in air; And the weightening finish process of sample, since ℃ left and right, 300 ℃ of left and right to 360, only increases weight 0.25% while testing in nitrogen.In air, sample after 340 ℃ of left and right reach maximum weight progressively burning weight loss finally to the complete (completenesss of combustion: 109.67%-10.28%=99.39%) of about 560 ℃ burnings.In whole process, there are two kinds of different variations in sample, first fusing before 340 ℃ of left and right, and example weight does not reduce, because the participation of oxygen is risen on the contrary to some extent; Subsequently in conjunction with (physics or chemistry or both all have) macromolecular material generation polymer segment of oxygen cracked, decompose, further burning generates gaseous products, weight progressively alleviates, to 560 ℃ of abundant cracking in left and right burning completely.These two processes are presented as two exothermic peaks on spectrogram: 332.7 ℃ and 520.5 ℃.In nitrogen atmosphere, only have first process to occur, and owing to not having oxygen to participate in, the product after polymer segment is cracked cannot burn completely, weightlessness 35.46% (as Fig. 4) only in test specification.Thermogravimetric curve shows no matter be at air or in nitrogen, this material has more stable performance 400 ℃ of left and right.These unique Performance Characteristicses have great importance in the application aspect chemical protection for such material.
Embodiment 4
Nonflammable polymer adsorbing material is for the adsorbance of dynamic benzene
Dynamic Adsorption refers under steady temperature, the adsorbent of certain mass and constant speed containing benzene air stream through fully contacting for a long time and reaching balance.Its assay method carries out in strict accordance with " phenenyl absorbing amount mensuration " method in the 81st page of the < < Chemical Agent Resistant Material inspection technology > > of China Weapon Industry Corporation science and technology and Quality Supervision Bureau, the establishment of China Arms Industry quality association.Cardinal principle is: under the experiment condition of regulation, the gas that contains certain benzene vapor concentration is passed through to constant weight sorbing material sample continuously, after sample absorption benzene vapor, increase quality, weight after increasing by mensuration, thus record sample Dynamic Adsorption amount in special time under a certain vapor concentration.This test is a crucial reference index evaluating China's chemical protection equipment correlative protection material protection performance.The dynamic benzene adsorbance that Fig. 5 has provided the nonflammable sorbing material of macromolecule of being prepared by embodiment mono-is worth over time.The nonflammable adsorbent of macromolecule resin class is very fast to the adsorption rate of dynamic benzene, approaches maximum adsorption value 45% about 50 minutes, meets the related request of protective materials for China's occupational protection equipment completely.
Nonflammable polymer adsorbing material is for the adsorbance of static sarin simulant DMMP
Static Adsorption refers to that the adsorbent of certain mass reaches balance with quantitative saturated vapor through fully contacting for a long time.Its assay method is mainly to measure with reference to standard GB/T 6287-1986 < < molecular sieve Static Water determining adsorption method > >: the adsorbent of certain mass is fully contacted with static sarin simulant DMMP gas, get the gravimetric method that different time is measured adsorbent weight value added.The static DMMP adsorbance that Fig. 6 has provided a kind of nonflammable sorbing material of macromolecule of being prepared by embodiment mono-is worth over time.The static DMMP adsorbance of the nonflammable adsorbent of macromolecule resin class, in 4 days that start, absorption gathers way comparatively fast, and prolongation in time also has a slowly increase process for continuity always.
Nonflammable polymer adsorbing material is for the absorption evaluation of floating on water greasy dirt benzene
For the ease of observing the absorption effect of material to floating on water greasy dirt benzene, first, getting 5ml benzene and be placed in the measuring cup of 10ml, add wherein the molten type dye of micro-reddish oil, rock and evenly obtain the red benzole soln of clear.In 25ml beaker, add about 15ml deionized water, be placed on the balance that precision is 0.0001g, peeling is made zero.With dropper, to the water surface, drip the red benzole soln of above-mentioned preparation, form one deck water oil stain.Now write down the weight of floating on water benzene: 2.4829g, slowly to the water surface, add nonflammable sorbing material, can observe the surface that water oil stain is adsorbed to rapidly light yellow resin and present red aggregation, until the water surface no longer includes floating red benzole soln.Now write down the gross weight that adds benzene and resin material after sorbing material: 2.7616g.By calculating, can learn this sorbing material to the absorption efficiency of benzene up to 2.4829/ (2.7616-2.4829)=890.89%.Utilize this principle also can evaluate this material for the absorption ability of other floating on water greasy dirts.
Claims (2)
1. a polymer adsorbing material, is characterized in that this macromolecular material with arene derivatives and precursor chloromethane base class arene derivatives, pay continuously-Ke polymerization alkylation occurs under the effect of catalyst and reacts and obtain, and its reaction equation is:
X in formula, y are 1～6;
Concrete operation step is:
By phenmethylol, methyl phenyl ethers anisole, diphenyl ether, toluene, benzene, one or more arene derivatives in biphenyl and naphthalene and dichloride methyl benzene, chloromethylbenzene, to chloromethyl methoxybenzene, dichloride methyl biphenyl, chloromethyl biphenyl, chloromethyl naphthalene, chloromethylbenzene methyl alcohol, one or more chloromethane base class rigidity crosslinking agents in xylylene dichlorides or dichloromethyl biphenyl be take metering mol ratio and in solvent, are mixed as 1: 1～20, add catalyst, in temperature, be at 20～200 ℃, to react 3～144 hours, through water, ethanol, acetone washs 1～48 hour successively, then at 40～180 ℃, be dried and form for 3～72 hours, the agent structure feature of this material is the network system being formed by connecting with different repetitives by fragrant phenyl ring and methylene structure,
Catalyst is one or more in titanium tetrachloride, five vanadium chlorides, zinc chloride, zinc bromide, zinc acetate, trifluoroacetic acid zinc, alchlor, three fluosulfonic acid zinc, alchlor, three fluosulfonic acid aluminium, stannous chloride, butter of tin, anhydrous ferric trichloride, anhydrous ferric bromide, three fluosulfonic acid iron, boron trifluoride, boron chloride, Boron tribromide, perfluor triphenyl borine;
Solvent is one or more in chlorobenzene, o-dichlorohenzene, carrene, chloroform, carbon tetrachloride, monochlorethane, dichloroethanes, trichloroethanes, dichloro-propane, cyclohexane or nitrobenzene.
2. according to polymer adsorbing material claimed in claim 1, it is characterized in that polymer adsorbing material is at room temperature placed and be difficult for adsorbed water, specific area is 1300m
2more than/g, pore-size distribution is narrow, substantially concentrates on micropore and low side is mesoporous, to the adsorption capacity of aromatic hydrocarbons, dimethoxy-methyl phosphate DMMP organic molecule, is more than 400mg/g.
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| CN103463931B (en) * | 2013-10-08 | 2015-06-10 | 交通运输部水运科学研究所 | Adsorption device used for processing diffusion and volatilization of dangerous chemicals in inland water transport |
| CN104689797B (en) * | 2013-12-06 | 2017-04-05 | 中国石油天然气股份有限公司 | A kind of self-crosslinking polymer oil absorption material and preparation method thereof |
| CN105439830B (en) * | 2014-08-27 | 2018-02-13 | 中国石油化工股份有限公司 | In the method for paraformaldehyde synthesizing polyoxymethylene dimethyl ethers |
| CN106243442B (en) * | 2016-07-28 | 2018-08-03 | 上海超高环保科技股份有限公司 | There is the composition of high filtration to substance containing benzene |
| CN111169059A (en) * | 2018-11-09 | 2020-05-19 | 万喜人家(北京)健康科技有限公司 | Preparation method and preparation equipment of mesh-hole high-polymer film forming material |
| CN111171649A (en) * | 2018-11-09 | 2020-05-19 | 万喜人家(北京)健康科技有限公司 | Preparation method and preparation equipment of shell water-based paint with mesh-hole polymer as film-forming material |
| CN113019211A (en) * | 2018-11-09 | 2021-06-25 | 万喜人家环保科技有限责任公司 | Preparation equipment of shell powder dry powder type coating |
| CN113856645B (en) * | 2021-09-13 | 2022-10-14 | 山东大学 | Tetraene silane-polystyrene adsorbent |
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