CN103772605B - A kind of preparation method of cationic polymers - Google Patents
A kind of preparation method of cationic polymers Download PDFInfo
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- CN103772605B CN103772605B CN201410032388.3A CN201410032388A CN103772605B CN 103772605 B CN103772605 B CN 103772605B CN 201410032388 A CN201410032388 A CN 201410032388A CN 103772605 B CN103772605 B CN 103772605B
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Abstract
The invention discloses a kind of preparation method of cationic polymers.The structural formula of described cationic polymers is such as formula shown in I; The method comprises the steps: (1) 3-butene-1-ol and sodium hydroxide carry out being obtained by reacting 3-butene-1-ol sodium; (2) hexamethyl chloroguanide and described 3-butene-1-ol sodium carry out being obtained by reacting cationic monomer three (dimethylamino) methyl-3-butenyl ether hydrochloride, shown in II, (3) under emulsifying agent and initiator existent condition, namely acrylamide and described three (dimethylamino) methyl-3-butenyl ether hydrochloride obtain the cationic polymers shown in formula I through inverse emulsion polymerization.Cationic polymers prepared by the inventive method can be used as a kind of organic floculant, has good water solubility, the feature such as easy to use, is specially adapted to solve due to oil in water emulsion in the oily(waste)water of viscous crude field output, problem that admittedly outstanding thing clearance is low.In addition, it is few that this flocculation agent also has scum silica frost growing amount, the advantage that in scum silica frost, water ratio is low, oil length is high.
Description
Technical field
The present invention relates to a kind of preparation method of cationic polymers, belong to synthesis of polymer material field.
Background technology
Increase containing poly-concentration along with in Bohai Bay Oil viscous oil recovery degree and Produced Liquid, the sewage water yield, change of water quality are large, and viscous crude density is comparatively large, acid number is higher, profit density difference is little, emulsification is serious, requires higher, be difficult to be effectively addressed with general inorganic flocculation agent to processing technological flow and medicament.Under existing sewage treatment process first grade subsides cascade filtration flow path conditions, want to improve wastewater treatment efficiency, then must screen or develop with strong points, and effective flocculation agent, to ensure condensed oil sewage process re-injection up to standard.
Organic floculant, compared with inorganic flocculating agent, has the features such as throwing amount is little, flocculation ability is strong, deoiling effect is good, the scum silica frost amount of generation is few.The Study and Development work of organic floculant is just set about by the U.S., Japan and the industrially developed country such as European as far back as the beginning of the sixties, the sewage disposal of many refinerys all uses organic floculant.There is hundreds of family in the factory of organic floculant, and its product category is various, trade names are complete, have wide range of applications, and the synthesis of organic polymer coargulator has become the important subject of field of fine chemical.Current domestic industry flocculation agent is based on cationic polyacrylamide, molecular weight is higher, from hundreds of thousands of to millions of, belong to low electric charge, high molecular type flocculation agent, flocculating effect is good, but dissolution rate is comparatively slow in water, and general merchandise is sold with pulvis and emulsion, use more difficult, need to solve more special administration apparatus.
Summary of the invention
The object of this invention is to provide a kind of preparation method of cationic polymers.
Shown in formula I, the preparation method of cationic polymers, comprises the steps:
In formula I, when m is number-average degree of polymerization, being the natural number between 2888 ~ 4129, when n is number-average degree of polymerization, is the natural number between 7684 ~ 27280;
When m is weight average degree of polymerization, being the natural number between 4393 ~ 6397, when n is weight average degree of polymerization, is the natural number of 11686 ~ 44601;
The molecular vibrational temperature index of described cationic polymers is 1.5 ~ 1.7;
(1) 3-butene-1-ol and sodium hydroxide carry out being obtained by reacting 3-butene-1-ol sodium;
(2) hexamethyl chloroguanide and described 3-butene-1-ol sodium carry out being obtained by reacting cationic monomer three (dimethylamino) methyl-3-butenyl ether hydrochloride, shown in II,
(3) under emulsifying agent and initiator existent condition, namely acrylamide and described three (dimethylamino) methyl-3-butenyl ether hydrochloride obtain the cationic polymers shown in formula I through inverse emulsion polymerization.
In above-mentioned preparation method, in step (2), the mol ratio of described hexamethyl chloroguanide and described 3-butene-1-ol sodium is 1:1;
The temperature of described reaction is 10 ~ 25 DEG C, and the time is 3 ~ 6 hours.
In above-mentioned preparation method, in step (3), the mol ratio of described acrylamide and described three (dimethylamino) methyl-3-butenyl ether hydrochloride can be 63 ~ 85:15 ~ 37, specifically can be 63:21,63:37 or 85:15.
In above-mentioned preparation method, in step (3), the solvent of described inverse emulsion polymerization reaction is the mixture of water and organic solvent;
Described water can be deionized water, and described organic solvent can be hexanaphthene;
The mass ratio of described water and described organic solvent can be 1:2.7;
Total add-on of described acrylamide and described three (dimethylamino) methyl-3-butenyl ether hydrochloride can be 44% of the aqueous phase quality that described inverse emulsion polymerization reacts, and described aqueous phase is the mixture of described water, described acrylamide and described three (dimethylamino) methyl-3-butenyl ether hydrochloride.
In above-mentioned preparation method, in step (3), described emulsifying agent is sorbitol anhydride oleate (Span-80) and/or sorbitan monooleate Soxylat A 25-7 (Tween-80);
The add-on of described emulsifying agent can be 10% of the oil phase quality of described inverse emulsion polymerization reaction, and described oil phase is the mixture of described organic solvent and described emulsifying agent.。
In above-mentioned preparation method, in step (3), described initiator is Potassium Persulphate/sodium bisulfite redox system, and the mass ratio of Potassium Persulphate and sodium bisulfite can be 3:1;
The add-on of described initiator can be 0.1 ~ 0.5% of described acrylamide and described three (dimethylamino) methyl-3-butenyl ether hydrochloride total mass, as 0.2%.
In above-mentioned preparation method, in step (3), the temperature of described inverse emulsion polymerization reaction can be 45 DEG C, and the time can be 4 hours.
In above-mentioned preparation method, in step (3), described phase emulsion polyreaction is carried out in atmosphere of inert gases.
Cationic polymers prepared by method provided by the invention can be any one in following 3 kinds:
1) cationic degree of described cationic polymers is 10.07%, and intrinsic viscosity is 855.9mL/g, and number-average molecular weight is 2.931 × 10
6g/mol, weight-average molecular weight is 4.792 × 10
6g/mol;
2) cationic degree of described cationic polymers is 18.76%, and intrinsic viscosity is 930.8mL/g, and number-average molecular weight is 2.612 × 10
6g/mol, weight-average molecular weight is 4.046 × 10
6g/mol;
3) cationic degree of described cationic polymers is 27.32%, and intrinsic viscosity is 983.4mL/g, and number-average molecular weight is 1.484 × 10
6g/mol, weight-average molecular weight is 2.257 × 10
6g/mol.
Cationic polymers prepared by method provided by the invention can be used as a kind of organic floculant, has good water solubility, the feature such as easy to use, is specially adapted to solve due to oil in water emulsion in the oily(waste)water of viscous crude field output, problem that admittedly outstanding thing clearance is low.In addition, it is few that this flocculation agent also has scum silica frost growing amount, the advantage that in scum silica frost, water ratio is low, oil length is high.
Accompanying drawing explanation
Fig. 1 is the hydrogen nuclear magnetic resonance spectrogram of three (dimethylamino) methyl-3-butenyl ether hydrochloride.
Fig. 2 is the hydrogen nuclear magnetic resonance spectrogram of cationic polymers MCF-1.
Fig. 3 is the hydrogen nuclear magnetic resonance spectrogram of cationic polymers MCF-2.
Fig. 4 is the hydrogen nuclear magnetic resonance spectrogram of cationic polymers MCF-3.
Fig. 5 is the GPC spectrogram of cationic polymers MCF-1 ~ MCF-3.
Embodiment
The experimental technique used in following embodiment if no special instructions, is ordinary method.
Material used in following embodiment, reagent etc., if no special instructions, all can obtain from commercial channels.
Multijaw cationic functional monomer three (dimethylamino) methyl-3-butenyl ether hydrochloride used in following embodiment 1-3 is prepared in accordance with the following methods:
(1) synthesis of hexamethyl chloroguanide
1. dimethylin-N, N-dimethyl chloride is for chlorine alkene imonium (C
5h
12cl
2n
2, 171.07g/mol) synthesis
Reaction equation is as follows:
Tetramethyl-urea (Chemical Reagent Co., Ltd., Sinopharm Group, the C of 1mol is added in two to 500mL there-necked flasks
5h
12n
2o, 116.16g/mol), the chloroform (Jinan chemical reagent work) of 200mL, under nitrogen protection, in reaction system, drip 2.1mol oxalyl chloride (Chemical Reagent Co., Ltd., Sinopharm Group, C
2h
2cl
2, 126.93g/mol) stir, oil bath reflux, react after 4 hours, be cooled to room temperature, underpressure distillation goes out concentrated solution, adds the anhydrous diethyl ether (Tianjin Bo Di Chemical Co., Ltd.) of 200mL, be cooled to 0 DEG C, the solid phase prod anhydrous diethyl ether of suction filtration gained repeatedly washs, vacuum-drying 24 hours, obtains white powder dimethylin-N, N-dimethyl chloride for chlorine alkene imonium, productive rate 83.9%.
2. hexamethyl chloroguanide (C
7h
18clN
3, 179.69g/mol) synthesis
Reaction equation is as follows:
In 250mL there-necked flask, add the dimethylin-N of 0.5mol, N-dimethyl chloride is for chlorine alkene imonium (C
5h
12cl
2n
2, 171.07g/mol), dimethyl amine (Chemical Reagent Co., Ltd., Sinopharm Group, the C of 0.6mol
2h
7n, 45.08g/mol) and 100mL anhydrous acetonitrile (Chemical Reagent Co., Ltd., Sinopharm Group, C
2h
3n, 41.05g/mol), after stirring at room temperature reacts 1 day, underpressure distillation obtains flaxen crude product, with anhydrous isopropyl alcohol (Tianjin chemical reagent one factory) washing, obtains white powdery solids, productive rate 78.6%.
(2) 3-butene-1-ol sodium (C
4h
7naO, 94.09g/mol) synthesis
Reaction equation is as follows:
3-butene-1-ol (Wuhan Fengfan Chemical Co., Ltd., the C of 2.1mol is added in the there-necked flask of 250mL
4h
8o, 72.11g/mol), the toluene (Chemical Reagent Co., Ltd., Sinopharm Group) of 150mL and the sodium hydroxide (Chemical Reagent Co., Ltd., Sinopharm Group, NaOH, 40.00g/mol) of 2.0mol, reflux divides water, goes out the water that reaction to the greatest extent generates.Reaction system concentrating under reduced pressure removing toluene, then with the unreacted 3-butene-1-ol of anhydrous diethyl ether washing removing, obtains white solid, yield 95.2%.
(3) three (dimethylamino) methyl-3-butenyl ether hydrochloride (C
11h
28cl
3n
3o, 324.72g/mol) synthesis
Reaction equation is as follows:
Under nitrogen protection, to the 3-butene-1-ol sodium (C of 0.5mol in the there-necked flask of 250mL
4h
7naO, 94.09g/mol), the ethylene dichloride (Ke Miou chemical reagent development centre, Tianjin) of 150mL and the hexamethyl chloroguanide (C of 0.5mol
7h
18clN
3179.69g/mol), stirring at room temperature reacts 6 hours, after reaction solution suction filtration, concentrating under reduced pressure is except desolventizing, and then add dehydrated alcohol (Tianjin chemical reagent two factory) suction filtration removing insolubles again, the crude product that underpressure distillation obtains, add tetrahydrofuran (THF) (Tianjin Bo Di Chemical Co., Ltd.) again, add concentrated hydrochloric acid (Yantai three and chemical reagent company limited) salify, suction filtration obtains white solid, vacuum-drying obtains monomer three (dimethylamino) methyl-3-butenyl ether hydrochloride, and yield is 85.5%.
The hydrogen nuclear magnetic resonance spectrogram of three (dimethylamino) methyl-3-butenyl ether hydrochloride of above-mentioned preparation as shown in Figure 1.
Analysis chart 1 is known, and structure is correct, obtains target compound.
The preparation of embodiment 1, cationic polymers MCF-1
Reaction equation is as follows:
By 22g acrylamide (Chemical Reagent Co., Ltd., Sinopharm Group) (C
3h
5nO, 71.08g/mol) be dissolved in 50mL deionized water obtain monomer solution with 18g tri-(dimethylamino) methyl-3-butenyl ether hydrochloride monomer, then monomer solution is added to containing 8.25gSpan-80(Jiangsu Hai'an Petrochemical Plant) and 6.75gTween-80(Jiangsu Hai'an Petrochemical Plant) 135g hexanaphthene (Chemical Reagent Co., Ltd., Sinopharm Group) in, at the emulsified 15min of high-shear homogeneous emulsifying machine, obtain emulsion.Above-mentioned emulsion is added in the 500mL four-necked bottle that agitator, thermometer, dropping funnel, ventpipe be housed, after stirring lower letting nitrogen in and deoxidizing 20min, drip the aqueous solution 10mL containing 0.06g Potassium Persulphate (Chemical Reagent Co., Ltd., Sinopharm Group) and 0.02g sodium bisulfite (Chemical Reagent Co., Ltd., Sinopharm Group), controlling temperature of reaction is 45 DEG C, stopped reaction after constant temperature 4h.Then add acetone precipitation, decompress filter, and with washing with acetone 2 times, suction filtration obtains granular product, vacuum-drying 12h at 50 DEG C.
Product prepared by the present embodiment represents with MCF-1, and productive rate is 90.23%, and cationic degree is 10.07%.
As shown in Figure 2, analyze this figure known, structure is correct for the hydrogen nuclear magnetic resonance spectrogram of product MCF-1.
The mensuration of intrinsic viscosity is carried out with reference to National Standard of the People's Republic of China GB12005.1-1989 polyacrylamide For Intrinsic Viscosity Measurements method, and recording intrinsic viscosity is 983.4mL/g.
As shown in Figure 5, GPC characterization result and polymkeric substance form as shown in table 1 the GPC spectrogram of product MCF-1.
The preparation of embodiment 2, cationic polymers MCF-2
16g acrylamide and 24g tri-(dimethylamino) methyl-3-butenyl ether hydrochloride monomer are dissolved in 50mL deionized water and obtain monomer solution, then monomer solution is added in the 135g hexanaphthene containing 8.25gSpan-80 and 6.75gTween-80, at the emulsified 10min of high-shear homogeneous emulsifying machine, obtain emulsion.Above-mentioned emulsion is added in the 500mL four-necked bottle that agitator, thermometer, dropping funnel, ventpipe be housed, after stirring lower letting nitrogen in and deoxidizing 20min, drip the aqueous solution 10mL containing 0.06g Potassium Persulphate and 0.02g sodium bisulfite, controlling temperature of reaction is 45 DEG C, stopped reaction after constant temperature 4h.Add acetone precipitation, decompress filter, washing with acetone 2 times, suction filtration obtains Powdered or granular product, vacuum-drying 12h at 50 DEG C.
Product prepared by the present embodiment represents with MCF-2, and productive rate is 86.01%, and cationic degree is 18.76%.
As shown in Figure 3, analyze this figure known, structure is correct for the hydrogen nuclear magnetic resonance spectrogram of product MCF-2.
The mensuration of intrinsic viscosity is carried out with reference to National Standard of the People's Republic of China GB12005.1-1989 polyacrylamide For Intrinsic Viscosity Measurements method, and recording intrinsic viscosity is 930.8mL/g.
As shown in Figure 5, GPC characterization result and polymkeric substance form as shown in table 1 the GPC spectrogram of product MCF-2.
The preparation of embodiment 3, cationic polymers MCF-3
11g acrylamide and 29g tri-(dimethylamino) methyl-3-butenyl ether hydrochloride monomer are dissolved in 50mL deionized water and obtain monomer solution, then monomer solution is added in the 135g hexanaphthene containing 8.25gSpan-80 and 6.75gTween-80, at the emulsified 15min of high-shear homogeneous emulsifying machine, obtain emulsion.Above-mentioned emulsion is added in the 500mL four-necked bottle that agitator, thermometer, dropping funnel, ventpipe be housed, after stirring lower letting nitrogen in and deoxidizing 20min, drip the aqueous solution 10mL containing 0.06g Potassium Persulphate and 0.02g sodium bisulfite, controlling temperature of reaction is 45 DEG C, stopped reaction after constant temperature 4h.Add acetone precipitation, decompress filter, washing with acetone 2 times, suction filtration obtains Powdered or granular product, vacuum-drying 12h at 50 DEG C.
Product prepared by the present embodiment represents with MCF-3, and productive rate is 81.95%, and cationic degree is 27.32%.
As shown in Figure 4, analyze this figure known, structure is correct for the hydrogen nuclear magnetic resonance spectrogram of product MCF-3.
The mensuration of intrinsic viscosity is carried out with reference to National Standard of the People's Republic of China GB12005.1-1989 polyacrylamide For Intrinsic Viscosity Measurements method, and recording intrinsic viscosity is 855.9mL/g.
As shown in Figure 5, GPC characterization result and polymkeric substance form as shown in table 1 the GPC spectrogram of product MCF-3.
The GPC characterization result of table 1 cationic polymers and polymkeric substance composition
The flocculating effect of embodiment 4, cationic polymers MCF-1-MCF-3
(1) crude oil
Test crude oil studies on asphaltene, saturated point, fragrance point and colloid be respectively 16.48wt%, 47.74wt%, 23.83wt% and 6.17wt%, reservoir temperature is 57 DEG C, and the apparent viscosity under 7.341/s is 70mPas.
(2) preparation of polymer-bearing waste-water is simulated
Bohai Sea oilfield injection is benefited well single well fluid lower floor water sample (filtering to remove the solid particulate in original water sample through 0.45 μm of cellulose microporosity filter membrane)+crude oil (crude oil namely in (1)), at 60 DEG C, high speed shear emulsification 15min under 10000r/min.The concentration measuring polymkeric substance in this Produced Liquid according to China National Offshore Oil Corporation (CNOOC) company standard Q/HS2032-2006 " performance index of offshore oilfield displacement of reservoir oil acrylic amide salt tolerant polymkeric substance and detection method " is 247.1mg/L.Bohai Sea oilfield injection is benefited well single well fluid lower floor water sample, and condition of water quality is as shown in table 2.
Draw a certain amount of lower floor with microsyringe and deviate from water in graduated cylinder, mix with 1:10 volume ratio with normal hexane again after dripping 5% hydrochloric acid of 2mL, after leaving standstill 10min, get upper layer of extraction liquid, measure oleaginousness with OilTech121A hand-held oil content analyzer.Simulated sewage initial oil content is 382.2mg/L.
Certain oil field simulated sewage water quality of table 2
(4) flocculation agent waste water dam
Weigh in the balance and get a certain amount of cationic polymers MCF-1-MCF-3(and be accurate to 0.01g), be placed in volumetric flask, shake up after being settled to scale, preparing massfraction is respectively the solution of 1% ~ 10%.The Wastewater Sample prepared is added, preheating 15min under 60 DEG C of waters bath with thermostatic control in the tool plug graduated centrifuge tube of 100 milliliters.The flocculant solution that quantitatively prepares is drawn in tool plug graduated centrifuge tube with microsyringe, put back to again after dandle 20 times in water bath with thermostatic control and leave standstill 15min, to measure before and after cationic polymers process oleaginousness and solid suspension content in water, result is as shown in table 3, and in table, the consumption of flocculation agent represents the amount of the flocculation agent added in every L Wastewater Sample.
Result shows, because oil-in-water drips with suspended solid all electronegative, along with the raising of cationic degree consumption, the flocculation ability of product increases, and oil removing and the effect except suspended solid strengthen.
Oleaginousness before and after table 3 sewage disposal and solid suspension content
Because cationic polymers provided by the invention has introducing that is hydrophobic and the multijaw type function monomer of high steric hindrance effect simultaneously, hydrophobicity makes the interaction of cationic polymers and oil droplet and suspended solids stronger on the one hand, on the other hand, high steric hindrance effect makes the chain rigidity of this polymkeric substance strengthen, structure in water is more unfolded, and bridging action increases.Above-mentioned reason enables cationic polymers and the non-polar component effect in sewage, strengthens the deoiling effect of polymkeric substance, thus enhances the application of flocculation agent in oily water treatment.
Claims (6)
1. the preparation method of cationic polymers shown in formula I, comprises the steps:
In formula I, when m is number-average degree of polymerization, being the natural number between 2888 ~ 4129, when n is number-average degree of polymerization, is the natural number between 7684 ~ 27280;
When m is weight average degree of polymerization, being the natural number between 4393 ~ 6397, when n is weight average degree of polymerization, is the natural number of 11686 ~ 44601;
(1) 3-butene-1-ol and sodium hydroxide carry out being obtained by reacting 3-butene-1-ol sodium;
(2) hexamethyl chloroguanide and described 3-butene-1-ol sodium react, and add concentrated hydrochloric acid salify, obtain cationic monomer three (dimethylamino) methyl-3-butenyl ether hydrochloride, shown in II,
The mol ratio of described hexamethyl chloroguanide and described 3-butene-1-ol sodium is 1:1;
The temperature of described reaction is 10 ~ 25 DEG C, and the time is 3 ~ 6 hours;
(3) under emulsifying agent and initiator existent condition, namely acrylamide and described three (dimethylamino) methyl-3-butenyl ether hydrochloride obtain the cationic polymers shown in formula I through inverse emulsion polymerization;
The temperature of described inverse emulsion polymerization reaction is 45 DEG C, and the time is 4 hours;
Described inverse emulsion polymerization reaction is carried out in atmosphere of inert gases.
2. preparation method according to claim 1, is characterized in that: in step (3), and the mol ratio of described acrylamide and described three (dimethylamino) methyl-3-butenyl ether hydrochloride is 63 ~ 85:15 ~ 37.
3. preparation method according to claim 1 and 2, is characterized in that: in step (3), and the solvent of described inverse emulsion polymerization reaction is the mixture of water and organic solvent;
Described water is deionized water, and described organic solvent is hexanaphthene;
The mass ratio of described water and described organic solvent is 1:2.7;
Total add-on of described acrylamide and described three (dimethylamino) methyl-3-butenyl ether hydrochloride is 44% of the aqueous phase quality that described inverse emulsion polymerization reacts, and described aqueous phase is the mixture of described water, described acrylamide and described three (dimethylamino) methyl-3-butenyl ether hydrochloride.
4. preparation method according to claim 3, is characterized in that: in step (3), and described emulsifying agent is sorbitol anhydride oleate and/or sorbitan monooleate Soxylat A 25-7;
The add-on of described emulsifying agent is 10% of the oil phase quality of described inverse emulsion polymerization reaction, and described oil phase is the mixture of described organic solvent and described emulsifying agent.
5. preparation method according to claim 1 and 2, is characterized in that: in step (3), and described initiator is Potassium Persulphate/sodium bisulfite redox system, and the mass ratio of Potassium Persulphate and sodium bisulfite is 3:1;
The add-on of described initiator is 0.1% ~ 0.5% of described acrylamide and described three (dimethylamino) methyl-3-butenyl ether hydrochloride total mass.
6. preparation method according to claim 1 and 2, is characterized in that: described cationic polymers is any one in following 3 kinds:
1) cationic degree of described cationic polymers is 10.07%, and intrinsic viscosity is 855.9mL/g, and number-average molecular weight is 2.931 × 10
6g/mol, weight-average molecular weight is 4.792 × 10
6g/mol;
2) cationic degree of described cationic polymers is 18.76%, and intrinsic viscosity is 930.8mL/g, and number-average molecular weight is 2.612 × 10
6g/mol, weight-average molecular weight is 4.046 × 10
6g/mol;
3) cationic degree of described cationic polymers is 27.32%, and intrinsic viscosity is 983.4mL/g, and number-average molecular weight is 1.484 × 10
6g/mol, weight-average molecular weight is 2.257 × 10
6g/mol.
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Address after: 100010 Beijing, Chaoyangmen, North Street, No. 25, No. Co-patentee after: CNOOC research institute limited liability company Patentee after: China Offshore Oil Group Co., Ltd. Address before: 100010 Beijing, Chaoyangmen, North Street, No. 25, No. Co-patentee before: CNOOC Research Institute Patentee before: China National Offshore Oil Corporation |
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