CN102604622A - Oil displacing agent containing imidazole ring quaternary ammonium salt polymer and preparation method - Google Patents
Oil displacing agent containing imidazole ring quaternary ammonium salt polymer and preparation method Download PDFInfo
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Abstract
The invention relates to an oil displacing agent containing an imidazole ring quaternary ammonium salt polymer for increasing the recovery ratio in oil fields and a preparation method. The polymer has good temperature resistance and salt tolerance capacity and shear resistance performance. The technical scheme of the oil displacing agent is as follows: the oil displacing agent comprises the following raw material monomers according to the mass percentage (gram is taken as the unit of mass): 59.5-79.5% of acrylamide AM, 20.4-39.5% of acrylic acid AA, and 0.1-1% of 1-allyl-3-oil acyloxy imidazole-1-ammonium bromide AOAB; the preparation method comprises the following steps of: firstly adding 10g of water in a flask, then adding 2.0g of AA and 1.1g of NaOH, adding 0.0453g of AOAB and 8.0g of AM after dissolving, adjusting pH to be 6-8, preparing into 10-20% of aqueous solution, and feeding nitrogen for 20min; then adding an initiator, continuously feeding the nitrogen for 10-20min, and reacting for 5-12h at the temperature of 30-70 DEG C; and finally, washing by using anhydrous ethyl alcohol, smashing and drying, and preparing the AM/AA/AOAB polymer. The polymer has better water solubility, temperature resistance, salt tolerance and shear resistance performance; and the indoor rock core flow test shows that the oil displacing agent can increase the recover rate of simulated crude oil by 8.9%.
Description
Technical field
The present invention relates to a kind of imidazole ring-containing QAS polymer oil-displacing agent and preparation method that oil recovery factor is improved in the oil field that be used for.
Background technology
At present, domestic and international most of oil field has all got into or has been about to get into tertiary phase (EOR).Usually, the oil field is used for the SEPIGEL 305 (HPAM) that the TOR polymer oil-displacing agent is mainly SEPIGEL 305 (PAM) and partly hydrolysed.Yet PAM or HPAM are at high shear forces, high salinity (Ca
2+, Mg
2+Deng), facile hydrolysis, degraded, chain curl etc. under the condition such as comparatively high temps, thereby the viscosity of PAM or HPAM sharply descended and do not reach the requirement of engineering construction.The polymer oil-displacing agent of therefore researching and developing special property such as a kind of anti-shearing, high temperature resistant, salt tolerant just seems particularly important.
Since the eighties in last century; Both at home and abroad a large amount of chemists has just launched the research (Sun Yuli to the polymer oil-displacing agent of heatproof, salt tolerant, property such as anti-shearing; Qian Xiaolin; Wu Wenhui. the progress of polymer displacement of reservoir oil tech. Speciality Petrochemicals progress .2005,7 (2), 26-29.).Wherein studying the most widely, polymer architecture mainly comprises: (1) suppresses the multipolymer of acrylamido hydrolysis, as:
N-vinyl pyrrolidone (NVP) multipolymer (Ling-ShuWan, et al. Copolymerization of acryl nitrile with
N-vinyL-2-pyrroL idone to improve the hem compatibility of polyacrylonitrile. Polymer. 2005. 46 (18): 7715-7723; Zhong Jingxing, etc. the solution property of AM/NVP copolymer. polymer material science and engineering. 2005,21 (4): 220-223),
N-replacement acryloyl or а-alkyl-substituted acrylamide.(2) have the multipolymer of the anionic group of strong hydrability; Like AMPS multipolymer (Hanbin Diao; Et al. High Performance Cross-Linked Poly (2-acrylamido-2-methylpropanesulfonic acid)-Based Proton Exchange Membranes for Fuel Cells. Macromolecules 2010; 43,6398 – 6405), the propenyl sulfonic acid copolymer (Zhang Chong is etc. the synthetic and performance evaluation of. temperature resistant antisalt polymer oil-displacing agent. oil and gas chemical industry. 2007; 24 (3): 228-231), vinyl sulfonic acid multipolymer, styrene sulfonic acid multipolymer (Jiguang Zhang; Matthew R. Dubay, Carl J. Houtman, and Steven J. Severtson. Sulfonated Amphiphilic Block Copolymers:Synthesis; Self-Assembly in Water; And Application as Stabilizer in Emulsion Polymerization. Macromolecules 2009,42,5080 – 5090).(3) but the multipolymer of complexing divalent-metal ion; As: acrylic amide, 3-acrylic amide-3 Methylbutanoic acid sodium and N-alkyl acrylamide terpolymer (Ou Yangjian; Deng. the solution properties of acrylic amide, 3-acrylic amide-3 Methylbutanoic acid sodium and N-alkyl acrylamide terpolymer research. the polymer circular. 2005. (1): 82-85) (4) have the functional group multipolymer of hydrophobic grouping, as the acrylic amide of 1933 years reports such as Hill with
N-4-ethylphenyl acrylic amide copolymerization parents' water-soluble polymerss.(5) comb-shaped polymer, star-type polymer, block polymer and network structure polymer etc.(6) QAS polymer (amphoteric ion copolymer) has been reported the serial amphoteric ion copolymer that utilized DMPS zwitter-ion function monomer and acrylic amide copolymerization like Han Yugui etc.(Han Yugui, Wang Qiuxia, He Shaoqun, Tan Yebang. the antiphase emulsifiable method preparation and the performance evaluation of water-soluble AM/DMPS ampholyte copolymer. Speciality Petrochemicals progress .2005,10,32-34).
Wherein, QAS polymer is one type of novel heatproof, the salt tolerant base polymer that developed recently gets up, because this base polymer is water-soluble, heatproof, salt resistant character well receive much concern.QAS polymer mainly contains following at present: and dimethyl diallyl ammonium chloride (DMDAAC) polymkeric substance (Cai Xinming, Liao Gang, Wang Wei. AM/AMPS/C
18Synthetic and the SOLUTION PROPERTIES research [J] of DMDAAC terpolymer. the Speciality Petrochemicals progress; 2005,6 (2): 15-18.), methylacryoyloxyethyl alkyl dimethyl ammonium chloride (DMAEMA); (Zhang Long; Synthetic and throwing out [J] Deng acrylic amide/Ethyl acrylate ammonium chloride multipolymer. polymer material science and engineering .1999,15,59-61; Song, B.K et al, Dispersion Polymerization of acrylamide with quaternary ammonium cationic comonomer in aqueous solution [J] .J Appl Polym Sci. 2003,87,1101-1108; Ryan Longenecker; Et al. Thermally Responsive 2-Hydroxyethyl Methacrylate Polymers:Soluble-Insoluble and Soluble-Insoluble-Soluble Transitions. Macromolecules. 2011; 44 (22), 8962 – 8971) etc.But the heatproof of these QAS polymers, salt tolerant, performance such as anti-shearing also can not satisfy the actual engineering construction needs in TOR far away.Therefore, still need research and develop out various novel structures in a large number, heatproof, salt tolerant, well behaved polymer oil-displacing agent such as anti-shearing.
In recent years, both at home and abroad the research of the quaternary ammonium salt of imidazole ring-containing is become one of focus of research gradually.[Shi Zeshi, military Tian Zhi, the safe history of gold, etc. imdazole derivatives or their salt [P]. Chinese patent: 1462270,2003-12-17; Gou defends army, Liu Xinqi. ion liquid sign and the application in organic synthesis [J] thereof. and Zhongzhou Univ.'s journal, 2007,2 (24): 116-118.], yet fewer for polymkeric substance that contains imidazole ring and oil-displacing agent research.Nursel P [Nursel P; Nurettin S; Et al. Synthesis and characteization of N-vinylimidazole-ethylmethacrylate copolymers and determination of monomer reactivity rations [J]. Europ Polym J; 2001; 37:2443-2451.] and Murat [Murat, Zuhal.K. Synthesis, characterization and electrical properties of iodinated poly (
N-vinylimidazole) [J]. Synthetic Metals, 1997,87:123-126.].In view of the advantageous property of quaternary ammonium salt aspect heatproof, salt tolerant; We intend performances such as the heatproof on polymer lateral chain, introducing the five-ring imidazoles quaternary ammonium salt structure that contains two nitrogen-atoms and strengthen polymkeric substance, salt tolerant; The electrostatic force of zwitterion in aqueous solutions of polymers that utilizes quaternary ammonium salt to produce waits viscosity and the rheological property that improves polymkeric substance, thereby prepares well behaved used for tertiary oil recovery polymer oil-displacing agents such as a kind of heatproof, salt tolerant.
Summary of the invention
The objective of the invention is to: have good heat-resistant salt-resistant ability in order to make polymkeric substance, can improve oil recovery factor preferably.The spy provides a kind of imidazole ring-containing QAS polymer oil-displacing agent and preparation method.
In order to reach above purpose, the present invention adopts following technical scheme:
A kind of imidazole ring-containing QAS polymer oil-displacing agent is by acrylic amide code name AM, vinylformic acid code name AA, the 1-allyl group-3-oil acyloxy AM/AA/AOAB ter-polymers that imidazoles-three kinds of structural units of 1-brometo de amonio code name AOAB constitute; Its structural formula is:
X in the formula, y, n is the polymerization degree, infrared spectrum is seen Fig. 1.The raw materials used monomer mass percentage ratio of this polymkeric substance is that quality is unit with the gram, AM59.5-79.5%, AA20.4-39.5%, AOAB0.1-1%; The method for making of monomer A OAB: in reactor drum, add 14.1g oleic acid, under agitation slowly add the 3.4g phosphorus trichloride, charge temperature is controlled at 10-15
oC finishes, and is warmed up to 55
oC divides sub-cloud liquid behind the insulation 2-6h, and upper strata liquid is removed responseless phosphorus trichloride through evaporation, and getting productive rate is the oleoyl chloride of 98-99.5%; It is for use with the tetrahydrofuran solvent dilution constant pressure funnel of packing into to go up the oleoyl chloride 5.0g that makes of step again; Add the 1.0g imidazoles at 50ml exsiccant single port flask; Dissolve with tetrahydrofuran solvent; Add 0.37-0.4gNaH again and make catalyzer, after under agitation above-mentioned liquid for use slowly being dripped off, using reflux again is 35 in temperature
oC reacts 6-10h, and reaction solution is used 2% caustic wash(ing) through washing, the saturated common salt washing, and dry filter makes behind the evaporating solvent
N-oily acyloxy imidazoles, productive rate 97-99.5%; In the 50ml flask, add above-mentioned
N-oily acyloxy imidazoles 5.0g adds the 1.8-2.1g allyl bromide 98 again, is 90 in stirring and temperature
oBehind the C refluxed 10h, reaction solution makes weak yellow liquid AOAB monomer after vacuumizing 1h and removing responseless allyl bromide 98.
The preparation method of this polymer oil-displacing agent: add the 10g deionized water earlier at the 250ml three-necked flask earlier; Add 2.0gAA and 1.1gNaOH more respectively; Wait to have dissolved postcooling to room temperature; Add again the above-mentioned preparation of 0.0453g AOAB and 8.0gAM, use NaOH solution to regulate pH to be 6-8, to be made into the monomer total mass percentage concentration 10-20% aqueous solution, logical nitrogen 20min; Add initiator ammonium persulfate solution and sodium sulfite solution then, ammonium persulphate and sodium sulfite anhy 96 mol ratio are 1:1, and the initiator add-on is the 0.1-0.5% of monomer total mass, continue to feed nitrogen 10-20min, and be 30-70 in temperature
oC is reaction 5-12h down; Using absolute ethanol washing at last three times, pulverize, is 40 in temperature
oC is oven dry down, makes the AM/AA/AOAB ter-polymers.
The application of this polymer oil-displacing agent is: it is the 1000mg/L aqueous solution that above-mentioned ter-polymers is mixed with concentration, and when shearing rate was 1.5r/min, AV was 176.4mPa.s, and total mineralization is 10000mg/L, simulating oil deposit temperature 65
oC; Simulated oil viscosity 72.48mPa.s, one dimension is filled out husky model,
Φ 25x500, water displacing oil; Mixed water injection water is with 1ml/min injection speed displacement simulation oil, and with injection speed 1ml/min, concentration is 1000mg/L, and IR is this polymers soln of 0.3PV, follow-up water 1ml/min, and water saturation reaches 98.5%.This polymkeric substance simulation improves oil recovery factor and can reach 7-10%.
The present invention has following beneficial effect: acrylic acid copolymer is directly used in (1), has introduced hydroxy-acid group, has increased the water-soluble of polymkeric substance; (2) five-ring of introducing in the polymer molecular chain that contains two nitrogen-atoms strengthens the rigidity of polymer molecular chain greatly, and the viscosity of polymkeric substance increases greatly; (3) thermostability that quaternary ammonium salt is stronger and electrostatic force have increased the heat-resistant salt-resistant property and the shear resistant of polymkeric substance.
Description of drawings
Fig. 1 is the infrared spectrum of AM/AA/AOAB polymkeric substance of the present invention.
Fig. 2 is the AV of AM/AA/AOAB polymers soln of the present invention and the relation of shearing rate.
Fig. 3 is the relation of AM/AA/AOAB polymers soln AV of the present invention and temperature.
Fig. 4 is the relation of AM/AA/AOAB polymers soln AV of the present invention and NaCl concentration.
Fig. 5 is AM/AA/AOAB polymers soln AV of the present invention and CaCl
2The relation of concentration.
Fig. 6 is AM/AA/AOAB polymers soln AV of the present invention and MgCl
2The relation of concentration.
Embodiment
The monomeric preparation of embodiment 1:AOAB
In reactor drum, add 14.1g oleic acid, under agitation slowly add the 3.4g phosphorus trichloride, charge temperature is controlled at 10
oC finishes, and is warmed up to 55
oC divides sub-cloud liquid behind the insulation 6h, and upper strata liquid is removed responseless phosphorus trichloride through evaporation, productive rate is 99.5% oleoyl chloride; It is for use with the tetrahydrofuran solvent dilution constant pressure funnel of packing into to go up the oleoyl chloride 5.0g that makes of step again; Add the 2.0g imidazoles at 50ml exsiccant single port flask; Dissolve with tetrahydrofuran solvent; Add 0.74gNaH again and make catalyzer, after under agitation above-mentioned liquid for use slowly being dripped off, use reflux 35 again
oC reacts 10h, and reaction solution is used 2% caustic wash(ing) through washing, the saturated common salt washing, and dry filter makes behind the evaporating solvent
N-oily acyloxy imidazoles, productive rate 98.3%; In the 50ml flask, add above-mentioned
N-oily acyloxy imidazoles 5.0g adds the 1.9g allyl bromide 98 again, and under agitation 90
oBehind the C backflow 10h, reaction solution makes weak yellow liquid AOAB monomer, productive rate 95% after vacuumizing 1h and removing responseless allyl bromide 98.
Embodiment 2: the preparation of polymer A M/AA/AOAB
Proportioning by table 1 takes by weighing AA and NaOH earlier, puts into the 250mL three-necked flask and uses deionized water dissolving, is cooled to room temperature; Add AM and AOAB, after room temperature was dissolved it fully, using NaOH solution regulation system pH was 8; Logical nitrogen 20min adds pre-assigned sodium sulfite solution, stirs 5min; Add ammonium persulfate solution again, continue logical nitrogen 20min, at constant temperature 45
oBehind the C lower seal reaction 12h, with absolute ethyl alcohol washing of precipitate three times, precipitated powder is broken into granule, soaked in absolute ethyl alcohol 2 days is in temperature 40
oC got polymer A M/AA/AOAB down in dry 2 days:
Table 1 polymer manufacture medicine dosage
| Medicine | Dosage (g) |
| AOAB | 0.0453 |
| Deionized water | 40.0000 |
| AM | 8.0000 |
| AA | 2.0000 |
| NaOH | 1.1060 |
| NaHSO 3 | 0.0064 |
| (NH 4) 2S 2O 8 | 0.0137 |
Embodiment 3:AM/AA/AOAB copolymer structure characterizes
The infrared spectrum of the polymer A M/AA/AOAB that embodiment 2 is prepared is as shown in Figure 1.From figure, learn 2923cm
-1And 2846cm
-1Be C-H (CH
3With-CH
2-) stretching vibration ,-N-H (NH
2), stretching vibration peak is at 3430cm
-1The place ,-C=O stretching vibration peak is at 1665cm
-1
The mensuration of embodiment 4:AM/AA/AOAB multipolymer relative molecular weight
With reference to GB/T 12005.10-92 " Molecular Weight for Polyacrylamide mensuration viscosimetry ", under embodiment 2 conditions, prepare terpolymer AM/AA/AOAB, be mixed with the solution of 0.1wt%, 30 ± 0.1
oUnder the C, the intrinsic viscosity that uses one point method to record this terpolymer is 1205mL/g.Utilize experimental formula M=802 [η]
1.25, M is sticking all relative molecular mass, and [η] is intrinsic viscosity, and 802,1.25 are empirical constant.It is 5.693878 * 10 that calculating can get the sticking all relative molecular weight of polymkeric substance
6
The investigation of the embodiment 5:AM/AA/AOAB multipolymer property sheared
The polymer formulation of embodiment 2 preparations is become the 0.3wt% aqueous solution, is 35 in temperature
oC, shearing rate is from 170s
-1Rise to 510s
-1, again from 510s
-1Drop to 170s
-1Under the condition, measure the AV changing conditions of polymers soln, data such as Fig. 2.Can find from Fig. 2: at constant shearing rate 170s
-1Following for some time, it is constant that apparent viscosity of polymer is tending towards; When unexpected rising shearing rate arrives 510s
-1The time, AV reduces, and this meets superpolymer fluidic character, when shearing rate is got back to 170s again
-1The time, AV almost surely is held in the value under the shearing rate of beginning again, and AV is 120mPa.S, and the result shows that fully this polymkeric substance is 35
oHave tangible viscosity save power under the C high shear rate condition, anti-shear performance is better.
Embodiment 6:AM/AA/AOAB multipolymer temperature tolerance is investigated
Embodiment 2 polymer formulation are become the 0.3wt% aqueous solution, are 22-122 in temperature
oUnder the C, measure the AV changing conditions of polymers soln, data such as Fig. 3.Can find from Fig. 3: apparent viscosity of polymer rises with temperature, and AV reduces gradually.When temperature is elevated to 62
oIn the time of C, viscosity retention ratio can reach 97.8%, when temperature rises to 100 again
oIn the time of C, viscosity retention ratio is 87.8%, is elevated to 120 yet work as temperature
oDuring C, AV sharply descends, and viscosity retention ratio is about 58.6%.The result indicates that this polymkeric substance is 100
oHas tangible viscosity save power below the C.
Embodiment 7:AM/AA/AOAB multipolymer salt resistance is investigated
It is the 3000mg/L aqueous solution that the polymkeric substance of embodiment 2 preparation is made into concentration, and it is a certain amount of to get liquid, adds NaCl, the CaCl of different amounts respectively
2, MgCl
2, 30
oUnder the C, use the BROOKFIELDDV-II+pro viscometer, 61
#The AV of rotor measurement solution, data such as Fig. 4-shown in Figure 6.NaCl, CaCl
2And MgCl
2Total trend is the increasing with outer salt adding amount, polymers soln AV all descend.When NaCl concentration reached 14000mg/L, its viscosity was 68.4mP.s; Work as CaCl
2When concentration reached 1400mg/L, its viscosity was 58.7mPa.s.MgCl
2When concentration reached 1200mg/L, its viscosity was 67mP.s.The result shows that polymkeric substance has anti-salt property preferably.
Embodiment 8:AM/AA/AOAB multipolymer improves RF (EOR) laboratory experiment
It is the 1000mg/L aqueous solution that the polymer formulation of embodiment 2 preparation is become concentration, when shearing rate is 1.5r/min,
-AV is 176.4mPa.s, total mineralization 10000mg/L (MgCl
2, NaCl, CaCl
2), simulating oil deposit temperature, 65
oC; Simulated oil viscosity: 72.48mPas (65
oC, shearing rate 7.34 S
-1), the one dimension sand-packed model:
Φ 25x500, water displacing oil: mixed water injection water is with 1 mL/min injection speed displacement simulation oil, and injecting IR with 1 mL/min is 0.3 PV, the 1000mg/L polymers soln, and follow-up water 1 ml/min, water saturation reaches 98.5%.With compare with doing displacement of reservoir oil laboratory experiment with clear water under the condition, this polymkeric substance improves Simulation of Crude Oil RF can reach 8.9%.
Claims (3)
1. imidazole ring-containing QAS polymer oil-displacing agent is characterized in that: this polymer oil-displacing agent comprises acrylic amide code name AM, vinylformic acid code name AA, 1-allyl group-3-oil acyloxy AM/AA/AOAB ter-polymers that imidazoles-three kinds of structural units of 1-brometo de amonio code name AOAB constitute; Raw materials used monomer mass percentage ratio is that quality is unit with the gram, AM59.5-79.5%, AA20.4-39.5%, AOAB0.1-1%; The method for making of monomer A OAB: in reactor drum, add 14.1g oleic acid, under agitation slowly add the 3.4g phosphorus trichloride, charge temperature is controlled at 10-15
oC finishes, and is warmed up to 55
oC divides sub-cloud liquid behind the insulation 2-6h, and upper strata liquid is removed responseless phosphorus trichloride through evaporation, and getting productive rate is the oleoyl chloride of 98-99.5%; It is for use with the tetrahydrofuran solvent dilution constant pressure funnel of packing into to go up the oleoyl chloride 5.0g that makes of step again; Add the 2.0g imidazoles at 50ml exsiccant single port flask; Dissolve with tetrahydrofuran solvent; Add 0.7-0.9gNaH again and make catalyzer, after under agitation above-mentioned liquid for use slowly being dripped off, using reflux again is 35 in temperature
oC reacts 6-10h, and reaction solution is used 2% caustic wash(ing) through washing, the saturated common salt washing, and dry filter makes behind the evaporating solvent
N-oily acyloxy imidazoles, productive rate 97-99.5%; In the 50ml flask, add above-mentioned
N-oily acyloxy imidazoles 5.0g adds the 1.8-2.1g allyl bromide 98 again, is 90 in stirring and temperature
oBehind the C refluxed 10h, reaction solution makes weak yellow liquid AOAB monomer after vacuumizing 1h and removing responseless allyl bromide 98.
2. the preparation method of an imidazole ring-containing QAS polymer oil-displacing agent as claimed in claim 1; It is characterized in that: add the 10g deionized water earlier at the 250ml three-necked flask earlier, add 2.0gAA and 1.1gNaOH more respectively, wait to have dissolved postcooling to room temperature; The AOAB and the 8.0gAM that add the above-mentioned preparation of 0.0453g again; Use NaOH solution to regulate pH and be 6-8, being made into monomer total mass percentage concentration is the 10-20% aqueous solution, logical nitrogen 20min; Add initiator ammonium persulfate solution and sodium sulfite solution then, ammonium persulphate and sodium sulfite anhy 96 mol ratio are 1:1, and the initiator add-on is the 0.1-0.5% of monomer total mass, continue to feed nitrogen 10-20min, and be 30-70 in temperature
oC is reaction 5-12h down; Using absolute ethanol washing at last three times, pulverize, is 40 in temperature
oC is oven dry down, makes the AM/AA/AOAB ter-polymers.
3. imidazole ring-containing QAS polymer oil-displacing agent according to claim 1; It is characterized in that: the application of this polymer oil-displacing agent: it is the 1000mg/L aqueous solution that the ter-polymers of above-mentioned preparation is mixed with concentration; When shearing rate is 1.5r/min; AV is 176.4mPa.s, and total mineralization is 10000mg/L, simulating oil deposit temperature 65
oC; Simulated oil viscosity 72.48mPa.s, one dimension is filled out husky model,
Φ 25x500, water displacing oil; Mixed water injection water is with 1ml/min injection speed displacement simulation oil, and with injection speed 1ml/min, concentration is 1000mg/L, and IR is this polymers soln of 0.3PV, follow-up water 1ml/min, and water saturation reaches 98.5%; This polymkeric substance simulation improves oil recovery factor and can reach 7-10%.
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| CN103570865A (en) * | 2012-07-27 | 2014-02-12 | 中国石油化工股份有限公司 | Acrylamide series terpolymer, preparation method, and applications thereof |
| CN103570867A (en) * | 2012-07-27 | 2014-02-12 | 中国石油化工股份有限公司 | Acrylamide series terpolymer, preparation method, and applications thereof |
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| CN103242818A (en) * | 2013-05-03 | 2013-08-14 | 西南石油大学 | AM (acrylamide)/NaAA (sodium acrylic acid)/AMPL (N-allyl morpholinium) ternary copolymer oil displacement agent and synthesis method thereof |
| CN104099080A (en) * | 2014-07-24 | 2014-10-15 | 西南石油大学 | Water-soluble quadripolymer oil displacement agent and preparation method thereof |
| CN104099080B (en) * | 2014-07-24 | 2017-01-11 | 西南石油大学 | Water-soluble quadripolymer oil displacement agent and preparation method thereof |
| CN104327278B (en) * | 2014-10-24 | 2017-02-15 | 中海油天津化工研究设计院有限公司 | Hydrophobic associated polymer oil-displacing agent containing chitosan and preparation method of hydrophobic associated polymer oil-displacing agent |
| CN104327278A (en) * | 2014-10-24 | 2015-02-04 | 中国海洋石油总公司 | Hydrophobic associated polymer oil-displacing agent containing chitosan and preparation method of hydrophobic associated polymer oil-displacing agent |
| CN104371691A (en) * | 2014-10-27 | 2015-02-25 | 西南石油大学 | Hydrophobically associating polymer sulfonate oil-displacing agent and synthesizing method thereof |
| CN104371691B (en) * | 2014-10-27 | 2017-02-15 | 西南石油大学 | Hydrophobically associating polymer sulfonate oil-displacing agent and synthesizing method thereof |
| CN106749891A (en) * | 2016-11-21 | 2017-05-31 | 中国石油大学(北京) | It is applicable amphoteric ion copolymer of drilling fluid filtrate reducing and its preparation method and application and drilling fluid and its application |
| CN106749836A (en) * | 2016-11-21 | 2017-05-31 | 中国石油大学(北京) | It is suitable to copolymer of filtrate reducing and its preparation method and application and drilling fluid and its application with temperature resistance anticalcium ability |
| CN106749891B (en) * | 2016-11-21 | 2018-03-20 | 中国石油大学(北京) | It is applicable amphoteric ion copolymer of drilling fluid filtrate reducing and its preparation method and application and drilling fluid and its application |
| CN113683725A (en) * | 2021-09-03 | 2021-11-23 | 东营科创生物化工有限公司 | Oil-water dual-response type active polymer and preparation method thereof |
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