CN105060445B - Positive ion organosilicone polyacrylamide flocculant and preparing method thereof - Google Patents
Positive ion organosilicone polyacrylamide flocculant and preparing method thereof Download PDFInfo
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Abstract
The invention discloses a positive ion organosilicone polyacrylamide flocculant and a preparing method thereof. The flocculant is obtained through induced polymerization with a compound initiator in the aqueous solution free radical micellar polymerization mode by means of a novel polymerizable organosilicone positive ion monomer (patent number: 201510384412.4). Due to the adoption of the novel polymerizable organosilicone positive ion monomer (patent number: 201510384412.4), the flocculant has high demulsification and degreasing performance and can adsorb organic matter in sewage efficiently. Organosilicone perssad enables interaction between polymer molecular chains to be improved, so that a stronger adsorption bridging effect is realized and higher flocculation capacity is obtained; meanwhile, the surface activity of a polymer can be improved, interaction with organic matter is sewage is improved, the hydrophilia of organic matter is reduced, demulsification and separation of organic matter contained in sewage are accelerated, and the flocculant can be widely applied to treatment of waste water with high organic content.
Description
Technical field
The present invention relates to a kind of organosilicon flocculant and preparation method thereof, particularly to a kind of cationic silicones polypropylene
The preparation method of amide flocculant.
Background technology
Organic polymer coargulator is that a class utilizes organic monomer to form through chemical polymerization or macromolecular compound copolymerization
Organic high molecular compound, makes it have charge neutrality characteristic owing to adding polar group on its macromolecular chain.Synthesize organic
High polymer coagulant can be divided into cationic, anionic, nonionic and amphoteric etc. multiple by institute's charged species.Cloudy from
Subtype have partially hydrolyzed polyacrylamide (PHPA), poly styrene sulfonate, polyacrylate etc..Nonionic have PAM, polyoxy second
Alkene, polyoxypropylene, polyvinyl alcohol etc..The flocculant flocculation of nonionic and anionic mainly act as main with bridging,
Therefore require that molecular weight very great talent is worked.
Negative charge is often carried on oil emulsion and particle surface in sewage, makes cationic flocculant be used as at oil-polluted water
Reason agent is extremely paid attention to.It can reduce oil droplet and the electric charge on suspended solid surface, reduces the stability of this system, also can be at oil droplet
And between suspended solids, produce bridging, it is allowed to into bulky grain and filters from water.Study at present and apply more organic sun
Ionic flocculant is mainly the copolymer of polyacrylamide and cationic monomer, base ammonia chloride-acrylamide as bright in dimethyl two
(PDADMA-AM) copolymer and (methyl) acryloyloxyethyl trimethyl ammonium chloride-acrylamide (DMC-AM) copolymer [3-6]
Deng.Charge density and the cationic degree of Organic Cationic Flocculant are the highest, and charge neutrality effect is the strongest, but cost is the highest.At present
In oil field, inorganic cation flocculant is modified or compounds and obtain by widely used flocculant mostly, organic
Although high polymer coagulant flocculating effect is good, but owing to price is higher, application is restricted.
Summary of the invention
It is an object of the invention to provide a kind of cationic silicones polyacrylamide flocculant.This flocculant introduces and can gather
Closing organosilicon cationic monomer, this organosilicon cationic monomer is to utilize dimethylaminoethyl acrylate or dimethylaminoethyl acrylate methyl
Prepared by the quaternary ammonium reaction of amino ethyl ester and halogenated silanes.This monomer utilizes the complexing between silicon and nitrogen to make flocculant
The Interaction enhanced of polymer molecule interchain, thus have higher adsorption bridging effect, therefore can obtain higher flocculation energy
Power；Meanwhile, the introducing of organosilicon radical can strengthen the surface activity of polymer, adds and mutual between Organic substance in sewage
Effect, reduces organic hydrophilic, accelerates breakdown of emulsion and separation that Organic substance contains sewage, and therefore the cation of the present invention is organic
Silicon polyacrylamide flocculant has efficient breaking milk and removing oil performance and to the absorption property of organic efficient in sewage.
Another object of the present invention is to provide the preparation method of a kind of cationic silicones polyacrylamide flocculant.Should
Preparation method is simple to operate, and raw material is cheap and easy to get, to equipment without particular/special requirement.
Technical scheme is as follows:
A kind of cationic silicones polyacrylamide flocculant, its structural formula is:
Wherein: R1 is H or CH3；R2, R3, R4 respectively H or organic group that carbon number is 1-10 or halogenated organyl group
Group；X is halogen.
A kind of cationic silicones polyacrylamide flocculant, utilizes polymerizable organosilicon cationic monomer, uses water-soluble
Liquid micellar free radical copolymerization mode, causes with composite initiator and is polymerized, and its reaction equation is as follows:
Wherein: wherein: R1 is H or CH3；R2, R3, R4 respectively H or organic group that carbon number is 1-10 or halo
Organic group；X is halogen.
The preparation method of cationic silicones polyacrylamide flocculant, comprises the following steps that
(1) by organosilicon cationic monomer, acrylamide, water by (20-30): (30-70): the mass ratio of 100 uniformly mixes
Close, prepare mixed solution.
(2) polymeric additive (dimethylaminoethyl acrylate (DA) or the methyl-prop that mass ratio is 0.5%-2% is added
Olefin(e) acid dimethylaminoethyl (DM)).
(3) it is stirred continuously under conditions of 25 DEG C of-35 DEG C of constant temperature, is passed through nitrogen with 25ml/min to 250ml/min simultaneously
30min-60min, discharges oxygen.
(4) adding mass ratio is that (initiator is potassium peroxydisulfate K to 0.05%-0.2% initiator2S2O8, azodiisobutyronitrile
AIBN and sodium sulfite NaHSO31:1:1 in mass ratio mixes).Stir, react 0.5h-2h.
(5) it is warming up to 70-80 DEG C, continues reaction 1h-5h, cooling discharging.
Currently preferred, in above-mentioned steps (1), the cationic monomer of addition, acrylamide, the mass ratio of water are (20-
30): (30-70): 100.
Currently preferred, the polymeric additive in above-mentioned steps (2) is dimethylaminoethyl acrylate (DA) or first
Base dimethylaminoethyl acrylate (DM).
Currently preferred, the polymeric additive mass ratio in above-mentioned steps (2) is 0.5%-2%.
Currently preferred, the initiator in above-mentioned steps (4) is potassium peroxydisulfate K2S2O8, azodiisobutyronitrile AIBN and
Sodium sulfite NaHSO31:1:1 in mass ratio mixes.
Currently preferred, the mass ratio of the initiator in above-mentioned steps (4) is 0.05%-0.2%.
Currently preferred, the optimum reacting time in above-mentioned steps (4) is 0.5h-2h.
Currently preferred, the optimal reaction temperature in above-mentioned steps (5) is 70 DEG C-80 DEG C, and optimum reacting time is 1h-
5h。
Wherein, above-mentioned organosilicon cationic monomer structure formula is:
Wherein: R1 is H or CH3；R2, R3, R4 respectively carbon atom is alkyl or the haloalkyl of 1-10；X is halogen.
Above-mentioned organosilicon cationic monomer is to utilize dimethylaminoethyl acrylate or (methyl) acrylate second
Prepared by the quaternary ammonium reaction of ester and halogenated silanes, its reaction equation is as follows:
Wherein: R1 is H or CH3；R2, R3, R4 respectively H or organic group that carbon number is 1-10 or halogenated organyl group
Group；X is halogen.
The preparation method of this polymerizable organosilicon cationic monomer, comprises the following steps that
(1) in the triangular flask of the jacketed equipped with backflow, add reaction dissolvent, be simultaneously introduced reactant 1 and halo silicon
Alkane, described reactant 1 is dimethylaminoethyl acrylate or (methyl) dimethylaminoethyl acrylate；
(2) adding a small amount of polymerization inhibitor, the concentration after its addition system is 20-100mg/L；
(3) by the magnetic agitation reaction 4～12h under the conditions of uniform temperature of the solution of step (2).
(4) the product decompression of the step (3) after reaction being terminated is distilled off solvent, obtains slightly yellow colloid substance, uses
Absolute ether or acetone soak extracted several times, remove impurity component, and vacuum drying obtains pressed powder.
Currently preferred, (methyl) dimethylaminoethyl acrylate in above-mentioned steps (1) and the proportioning of halogenated silanes
For 1:1～8:1 (mol ratio), most preferably 2:1～4:1.
Currently preferred, the reaction dissolvent in above-mentioned steps (1) is acetonitrile, acetone, ethanol, isopropanol and acetic acid second
Ester, preferably acetonitrile and ethyl acetate.
Currently preferred, the polymerization inhibitor in above-mentioned steps (2) can be hydroquinone, MEHQ, phenothiazine etc.,
Optium concentration is 20-100mg/L.
Currently preferred, the reaction temperature in above-mentioned steps (3) is 10-60 DEG C, and optimal reaction temperature is 35 DEG C-45
DEG C, the response time is 4～12h.
Accompanying drawing explanation
The present invention is further described with embodiment below in conjunction with the accompanying drawings.
Fig. 1 flocculant 30DMESi infrared spectrogram；
Fig. 2 flocculant oil removing Evaluation results.
Detailed description of the invention
Below in conjunction with instantiation, the present invention is further described, but institute of the present invention protection domain is not limited to this.
Raw materials used in example it is conventional commercial products.
Acrylamide (AM), technical grade, Shandong Bao Mo biochemical industry company limited；Dimethylaminoethyl Methacrylate
(DM), technical grade, Yantai spark Chemical Co., Ltd.；Dimethylamino ethyl acrylate (DA), technical grade, Yantai spark chemical industry has
Limit company；Potassium peroxydisulfate K2S2O8(KPS), analytical pure, Chinese Medicine Chemical Group；Sodium sulfite NaHSO3, analytical pure, in
State's medicine Chemical Group；Azodiisobutyronitrile AIBN, analytical pure, Chinese Medicine Chemical Group；Sodium formate, analytical pure, middle traditional Chinese medical science
Medicine Chemical Group；Trim,ethylchlorosilane: technical grade, Dongying Sheng Kai industry and trade Co., Ltd；Chlorotriethyl silane: technical grade,
Dongying Sheng Kai industry and trade Co., Ltd；Tributyl chlorosilane: technical grade, Dongying Sheng Kai industry and trade Co., Ltd；To benzene two
Phenol and phenothiazine, analytical reagent, Chinese Medicine group；Sodium chloride, dehydrated alcohol, acetone, acetonitrile and ether, analytical pure, sky
Jinshi City's chemical reagent factory.Nitrogen gas purity: 99.99%；Distilled water.
Embodiment 1
The preparation of polymerizable organosilicon cationic monomer: precise dimethylamino ethyl acrylate (DA) 7.86g
(0.05mol) in the triangular flask of the jacketed equipped with backflow, it is simultaneously introduced 3.93g (0.036mol) trim,ethylchlorosilane, adds
Enter 50ml acetonitrile, be subsequently adding 2mg hydroquinone of polymerization retarder (or phenothiazine).By above-mentioned solution magnetic force under the conditions of 45 DEG C
Stirring reaction 12h.Product decompression after reaction being terminated is distilled off solvent, obtains slightly yellow colloid substance, uses absolute ether
Or acetone soak extracted several times, remove impurity component, vacuum drying obtains organosilicon cationic monomer dimethyl [2-(acryloyl
Oxygen ethyl) ethyl]-trimethyl silane ammonium chloride (DAMSC) pressed powder.
The preparation of cationic silicones polyacrylamide flocculant: by dimethyl [2-(methylacryoyloxyethyl) second
Base]-triethyl silicane ammonium chloride (DMESC), acrylamide, water uniformly mixes by the mass ratio of 30:70:100, prepares mixing molten
Liquid.Add the polymeric additive (dimethylaminoethyl methacrylate (DM)) that mass ratio is 1.5%.Condition at 30 DEG C of constant temperature
Under be stirred continuously, be simultaneously passed through nitrogen 30min with 25ml/min, discharge oxygen.Adding mass ratio is that 0.05% initiator (causes
Agent is potassium peroxydisulfate K2S2O8, azodiisobutyronitrile AIBN and sodium sulfite NaHSO31:1:1 in mass ratio mixes).Stir
Mix uniformly, react 0.5h.It is warming up to 70-80 DEG C, continues reaction 2h, cooling discharging, obtain cationic silicones polyacrylamide
Flocculant (code name: 30DMESi).
Embodiment 2:
The preparation of polymerizable organosilicon cationic monomer: precise dimethylamino ethyl acrylate (DA) 7.86g
(0.05mol) in the triangular flask of the jacketed equipped with backflow, it is simultaneously introduced 3.93g (0.036mol) trim,ethylchlorosilane, adds
Enter 50ml acetonitrile, be subsequently adding 2mg hydroquinone of polymerization retarder (or phenothiazine).By above-mentioned solution magnetic force under the conditions of 45 DEG C
Stirring reaction 12h.Product decompression after reaction being terminated is distilled off solvent, obtains slightly yellow colloid substance, uses absolute ether
Or acetone soak extracted several times, remove impurity component, vacuum drying obtains organosilicon cationic monomer dimethyl [2-(acryloyl
Oxygen ethyl) ethyl]-trimethyl silane ammonium chloride (DAMSC) pressed powder.
The preparation of cationic silicones polyacrylamide flocculant: by dimethyl [2-(acrylyl oxy-ethyl) ethyl]-three
Methyl silane chlorinating ammonium (DAMSC), acrylamide, water are uniformly mixed by the mass ratio of 30:70:100, prepare mixed solution.Add
Enter the polymeric additive (dimethylamino ethyl acrylate (DA)) that mass ratio is 1.5%.Constantly stir under conditions of 30 DEG C of constant temperature
Mix, be passed through nitrogen 30min with 25ml/min simultaneously, discharge oxygen.Adding mass ratio is that (initiator is over cure to 0.05% initiator
Acid potassium K2S2O8, azodiisobutyronitrile AIBN and sodium sulfite NaHSO31:1:1 in mass ratio mixes).Stir,
Reaction 0.5h.It is warming up to 70-80 DEG C, continues reaction 2h, cooling discharging, obtain cationic silicones polyacrylamide flocculant
(code name: 30DAMSi).
Embodiment 3:
The preparation of polymerizable organosilicon cationic monomer: precise dimethylamino ethyl acrylate (DA) 15.72g
(0.10mol) in the triangular flask of the jacketed equipped with backflow, it is simultaneously introduced 3.93g (0.026mol) chlorotriethyl silane, adds
Enter 70ml ethyl acetate, be subsequently adding 2mg hydroquinone of polymerization retarder (or phenothiazine).By above-mentioned solution under the conditions of 40 DEG C
Magnetic agitation reaction 8h.Product decompression after reaction being terminated is distilled off solvent, obtains slightly yellow colloid substance, uses anhydrous second
Ether or acetone soak extracted several times, remove impurity component, and vacuum drying obtains organosilicon cationic monomer dimethyl [2-(propylene
Acyloxyethyl) ethyl]-triethyl silicane ammonium chloride (DAESC) pressed powder.
The preparation of cationic silicones polyacrylamide flocculant: by dimethyl [2-(acrylyl oxy-ethyl) ethyl]-three
Ethylsilane ammonium chloride (DAESC), acrylamide, water are uniformly mixed by the mass ratio of 30:70:100, prepare mixed solution.Add
Enter the polymeric additive (dimethylamino ethyl acrylate (DA)) that mass ratio is 1.5%.Constantly stir under conditions of 30 DEG C of constant temperature
Mix, be passed through nitrogen 30min with 25ml/min simultaneously, discharge oxygen.Adding mass ratio is that (initiator is over cure to 0.05% initiator
Acid potassium K2S2O8, azodiisobutyronitrile AIBN and sodium sulfite NaHSO31:1:1 in mass ratio mixes).Stir,
Reaction 0.5h.It is warming up to 70-80 DEG C, continues reaction 2h, cooling discharging, obtain cationic silicones polyacrylamide flocculant
(code name: 30DAESi).
Interpretation of result 1:
According to embodiment 1,2,3, prepare molecular weight respectively and be about 3,000,000, with different cationic monomers be
Row polyacrylamide flocculant, is shown in Table 1.
Table 1 cationic silicones polyacrylamide flocculant sample
Interpretation of result 2:
We have carried out infrared spectrum characterization to the product (30DMESi) in embodiment 1, and characterization result is shown in Table 2 and schemes
1。
The IR spectrum elucidation of table 2 30DMESi flocculant
Knowable to infrared spectrum analysis, sample presents the characteristic peak of cationic monomer and acrylamide copolymerization product.Product
Significantly increase the distinctive 958-987cm of quaternary ammonium salt-1N at wave number+(CH3) C-N stretching vibration, 1190cm-1At wave number
Si(CH3)3Bending vibration and 1671cm-1And 3434.9cm-1The characteristic peak of place's acrylamide.Analyzed from above, made
Standby PAMC contains required functional group, and the characteristic peak of each functional group all occurs in infrared spectrum, it was demonstrated that this
Product is object.
Interpretation of result 3:
We utilize spectrophotography, according to oil and gas industry standard SY/T 0530-93 to embodiment 1,2,3
The flocculant of middle acquisition carries out the evaluation of oil removing performance, and evaluation result is shown in Fig. 2.
Find out, after adding the flocculant of different model, binary drive water exit is had oil removing effect from evaluation result, and
Along with the increase of dosage, oil removal rate increases therewith, and water quality becomes clear.But, the flocculant deoiling effect of different model is different.Adding
When measuring identical, sample oil removal rate is: 30DAESi > 30DAMSi > 30DMESi.
Claims (5)
1. a cationic silicones polyacrylamide flocculant, its structural formula is as follows:
Wherein: R1For H or CH3；R2、R3、R4It is respectively alkyl or haloalkyl that carbon atom is 1-10；X is halogen.
2. a kind of cationic silicones polyacrylamide flocculant described in claim 1, utilize polymerizable organosilicon sun from
Sub-monomer, uses aqueous free radical micellar copolymerization mode, causes being polymerized with composite initiator, described organosilicon sun from
Sub-monomer is；
Wherein: R1For H or CH3；R2、R3、R4It is respectively alkyl or haloalkyl that carbon atom is 1-10；X is halogen.
3. a preparation method for the cationic silicones polyacrylamide flocculant described in claim 1 or 2, including step
As follows:
(1) by organosilicon cationic monomer, acrylamide, water by (20-30): (30-70): the mass ratio of 100 uniformly mixes, system
Obtain mixed solution；
(2) adding mass ratio is the polymeric additive of 0.5%-2%；
(3) it is stirred continuously under conditions of 25 DEG C of-35 DEG C of constant temperature, is passed through nitrogen with 25ml/min to 250ml/min simultaneously
30min-60min, discharges oxygen；
(4) adding mass ratio is that 0.05%-0.2% initiator stirs, and reacts 0.5h-2h；
(5) it is warming up to 70-80 DEG C, continues reaction 1h-5h, cooling discharging.
4. according to the preparation method of the cationic silicones polyacrylamide flocculant described in claim 3, it is characterised in that
Polymeric additive in step (2) is dimethylaminoethyl acrylate or dimethylaminoethyl methacrylate.
5. according to the preparation method of the cationic silicones polyacrylamide flocculant described in claim 3, it is characterised in that
Initiator in step (4) is potassium peroxydisulfate K2S2O8, azodiisobutyronitrile AIBN and sodium sulfite NaHSO3In mass ratio 1:
1:1 mixes.
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| CN105418815A (en) * | 2015-11-24 | 2016-03-23 | 宜兴市丰烨化学有限公司 | Acrylamide and ethylenediamine flocculating agent and preparation method thereof |
| CN105418816A (en) * | 2015-11-24 | 2016-03-23 | 宜兴市丰烨化学有限公司 | Acrylamide and ethyl alcohol flocculating agent and preparation method thereof |
| CN111848859B (en) * | 2020-08-14 | 2021-09-14 | 山东大学 | Micro-crosslinked cationic polyacrylamide flocculant and preparation method and application thereof |
| CN112322133A (en) * | 2020-12-03 | 2021-02-05 | 上海瑞君电泳涂料有限公司 | Thick film impact-resistant corrosion-resistant cathode electrophoretic coating and preparation process thereof |
| CN114276489B (en) * | 2022-03-03 | 2022-05-13 | 河南博源新材料有限公司 | Silicon-containing cationic polyacrylamide and application thereof |
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| CN101205300A (en) * | 2007-11-30 | 2008-06-25 | 北京化工大学 | Polyethylene polyamine organosilicon cationic polymer and method for making same |
| JP5621254B2 (en) * | 2009-12-24 | 2014-11-12 | 三菱レイヨン株式会社 | Oil-containing wastewater treatment method |
| CN101786647B (en) * | 2010-03-19 | 2012-05-23 | 常州友邦净水材料有限公司 | Accelerating sedimentation type flocculating agent for removing insoluble substances in polyaluminum chloride and preparation method thereof |
| CN102649830B (en) * | 2012-05-17 | 2013-11-27 | 陕西科技大学 | Preparation method of cation organic silicon modified polyacrylamide |
| JP6088386B2 (en) * | 2013-08-22 | 2017-03-01 | 株式会社日立製作所 | Water treatment method and organic acid flocculant |
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