CN108130065B - It is a kind of for improving the nano-complex of high temperature flooding polymers long-time stability - Google Patents
It is a kind of for improving the nano-complex of high temperature flooding polymers long-time stability Download PDFInfo
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- CN108130065B CN108130065B CN201810060400.XA CN201810060400A CN108130065B CN 108130065 B CN108130065 B CN 108130065B CN 201810060400 A CN201810060400 A CN 201810060400A CN 108130065 B CN108130065 B CN 108130065B
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
- C09K8/588—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids characterised by the use of specific polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine
- C08F220/585—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine and containing other heteroatoms, e.g. 2-acrylamido-2-methylpropane sulfonic acid [AMPS]
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2208/00—Aspects relating to compositions of drilling or well treatment fluids
- C09K2208/10—Nanoparticle-containing well treatment fluids
Abstract
The present invention relates to a kind of for improving the nano-complex of high temperature flooding polymers long-time stability, belongs to technical field of oilfield chemistry.2- acrylamide-2-methyl propane sulfonic is added in hectorite nanometer disperse system, promote the stably dispersing performance of nanometer disperse system, again by the components addition system such as polyethyleneimine, acrylamide, using potassium peroxydisulfate as initiator, organic-inorganic nanocomposite object is synthesized.This compound has good dissolution and dispersion performance in water, there are many functional groups for band in its molecular structure, there is interaction well with acrylic amide flooding polymers molecule, be suitable for improving the auxiliary agent of stability as under flooding polymers long term high temperature aging.
Description
Technical field
The present invention relates to a kind of for improving the nano-complex of high temperature flooding polymers long-time stability, belongs to oil field
Learn technical field.
Background technique
Petroleum is indispensable one of the non-renewable resources of modern society, its exploitation and utilizes the hair to national economy
Exhibition plays an important role.With the continuous progress of oil exploitation, currently, most of China's developed field enters High water cut
Phase, only by tertiary oil recovery technology can constant rate of production, improve oil recovery factor.Chemical flooding is that China is main to be adopted three times
One of oil tech, in the implementation process of chemical flooding, water-soluble polymer is one of key chemical agent, passes through the thickening of polymer
Property expand displacing fluid swept volume, the purpose for increasing substantially oil recovery factor may be implemented.However, common displacement of reservoir oil polymerization
Object, such as acrylamide copolymer, are suitable only for low-temperature reservoir, under the extreme reservoir condition of high temperature and high salt, their thickening
Performance is remarkably decreased, in addition, the amide groups in polymer molecule gradually hydrolyzes and becomes carboxyl at high temperature, their dissolubility and
The tackifying ability of molecular backbone bad stability, polymer is remarkably decreased.Therefore, improve polymer at high temperature steady in a long-term
Property, expand its application field, it is extremely urgent.
In order to improve the temperature-resistant anti-salt performance of flooding polymers, people are often in the molecular structure of acrylamide copolymer
Upper introducing other function unit, such as sulfonic group, pyrrolidone-base, caprolactam base, phenyl etc., to improve polymer molecular chain
Rigidity and hydrolytic Resistance；There are also chain alkyl, long carbon fluorine chain section, polyoxyethylene segment, internal salt structures etc., to promote polymerization
Interaction between object strand.
Chinese patent document CN 102181010A discloses a kind of preparation method of Heat Resistant and Salt Tolerant Polymer, preparation method
It is as follows: by anionic monomer, acrylic sodium sulfonate, cationic monomer, acrylate, alpha-olefin and acrylamide be dissolved in from
In sub- water, surfactant is added, adjusts under the conditions of pH value of solution is 9~10,30~60 DEG C and leads to nitrogen 30 minutes, over cure is added
Hydrochlorate initiator reacts 12h under the conditions of 30~60 DEG C of temperature, and with acetone precipitation, washing, vacuum drying obtains white powder
Polymer, resulting polymers can be used on enhancing oil recovery in polymer flooding.
Chinese patent document CN 103320111A discloses a kind of synthetic method of quadripolymer oil displacement agent, the displacement of reservoir oil
Agent is the function prepared by acrylamide (AM), acrylic acid (AA), n-vinyl pyrrolidone (NVP), ethylenediamine and maleic anhydride
The quadripolymer that energy monomer (YEML) is constituted.Its synthetic method is that YEML monomer obtained is first added in flask, is added
AM, NVP, AA and NaOH lead to nitrogen 30min, initiator are then added, and continue logical 10~20min of nitrogen, at 30~60 DEG C of temperature
4~12h of lower reaction.It finally washed, crushed with dehydrated alcohol, drying obtained AM/AA/NVP/YEML quadripolymer, preparation
Polymer can be used to improve oil recovery factor.
Above-mentioned patent realizes the promotion of polymer temperature-resistant anti-salt performance by introducing functional unit, in the process,
It often has the disadvantage that function monomer preparation process is cumbersome, there are the subsequent operations such as purification, increase product cost；With third
Acrylamide monomer is compared, and function monomer polymerization activity is poor, and polymer molecular weight is not high, in use process, the polymer that needs
Concentration is high；The introducing of hydrophobic type function monomer, interior salt form function monomer, reduces the solubility property of polymer, in use process,
The dissolution time of polymer increases, and insoluble matter ratio increases, and influences using and promoting for product.
Hectorite is a kind of Layered Lithium smectite-group clay synthesized by inorganic salts, and in aqueous solution, hectorite particle is in
Monodispersity is good discoid, and grain thickness is about 1nm, and diameter is about 30nm, and chemical formula is [(Si8(Mg5.34Li0.66)O20
(OH)4]Na0.66, hectorite particle is negatively charged.In aqueous solution, hectorite has very big specific surface area, and surface is contained largely
Oxygen atom and hydroxyl, therefore, the groups such as amide groups, carboxyl, sulfonic group in hectorite and acrylamide copolymer molecule have
There is good interaction.
However, the dispersion performance of hectorite nanometer system is very sensitive for the variation of external condition, it is few when having in solution
When measuring salt or polymer, hectorite nano particle will be coalesced and be settled；Studies have shown that hectorite granular absorption 2- acryloyl
After amine -2- methyl propane sulfonic acid, dispersibility is significantly improved, and nanometer point can be kept in macromolecule and ionic comonomer solution
Bulk state, and then the inorganic-organic composites with nanometer hectorite component can be prepared.
Summary of the invention
In view of the deficiencies of the prior art, the present invention provides a kind of for improving receiving for high temperature flooding polymers long-time stability
Rice compound.
Term explanation
Hectorite: also known as lithium magnesium silicate, the entitled Laponite of English, it is a kind of artificial synthesized trioctahedron lamellar gel
Material has extremely strong gel-forming property in aqueous systems, has excellent thixotropy, dispersibility, suspension and thickening property, commercially available production
Product.
Summary of the invention
The present invention selects 2- acrylamide-2-methyl propane sulfonic to modify hectorite nano particle, prepares in macromolecule and salt
The nanometer disperse system that can be stabilized in solution is further modified followed by the cationic character of polyethyleneimine
Hectorite particle, on this basis, by between the water-soluble monomers such as 2- acrylamide-2-methyl propane sulfonic, acrylamide
Copolymerization, prepares organic-inorganic nanocomposite object.By test, which has excellent dissolution and dispersion performance in the solution, adds
Enter in acrylic amide flooding polymers solution, their thickening and high-temperature long term stability energy can be significantly improved.
Detailed description of the invention
Technical scheme is as follows:
It is a kind of for improving the nano-complex of high temperature flooding polymers long-time stability:
(1) polyethyleneimine-hectorite nanometer disperse system preparation
It disperses hectorite in 2- acrylamide-2-methyl propane sulfonic solution, stirs 24~48h, prepare hectorite and receive
The polyethylenimine solution that concentration is 100~600g/L is then added drop-wise in hectorite nanometer disperse system by rice dispersion,
While be added dropwise while stir, and control pH be 1~6, be added dropwise stir 30min to get；The molecular weight of polyethyleneimine be 300~
The concentration of 20000,2- acrylamide-2-methyl propane sulfonic solution is 10~150g/L, hectorite and 2- acrylamide -2- methyl
The mass ratio of propane sulfonic acid is 1:(2~8), the mass ratio of hectorite and polyethyleneimine is 1:(0.1~5)；
(2) preparation of organic-inorganic nanocomposite object
Polyethyleneimine-hectorite nanometer disperse system and nonionic water-soluble monomers are added to equipped with blender, led to
In the wolf bottle of nitrogen pipe and thermometer, nitrogen 30min is stirred and is passed through, pH is controlled 2~6, potassium peroxydisulfate is then added,
60~90 DEG C are raised the temperature to, 1~10h is reacted, end of reaction is added NaOH solution for system pH and is adjusted to 8~9, and constant temperature is old
Change 0.5~1.5h, product is dry, crush to get；2- acrylamide-2-methyl propane sulfonic and nonionic water-soluble monomers
Mass ratio is 1:(0.1~5), the mass ratio of potassium peroxydisulfate and water-soluble monomer is 1:(100~1000).
, according to the invention it is preferred to, the molecular weight of polyethyleneimine is 1000~5000 in step (1)；
Preferably, the concentration of 2- acrylamide-2-methyl propane sulfonic solution is 25~100g/L, and polyethyleneimine amine concentration is
The mass ratio of 100~300g/L, hectorite and 2- acrylamide-2-methyl propane sulfonic is 1:(2~4), hectorite and polyethylene
The mass ratio of imines is 1:(0.2~2)；
Preferably, polyethylenimine solution is added drop-wise in hectorite nanometer disperse system, and pH is 1~4.
, according to the invention it is preferred to, nonionic water-soluble monomers described in step (2) are acrylamide, vinylpyridine
Pyrrolidone, Methacrylamide, N hydroxymethyl acrylamide, N- ethyl acrylamide, N, N- dimethacrylamide, N- isopropyl
One of base acrylamide, hydroxy-ethyl acrylate, hydroxypropyl acrylate or two or more mixtures；
Preferably, the mass ratio of 2- acrylamide-2-methyl propane sulfonic and nonionic water-soluble monomers be 1:(0.5~
1.5), the mass ratio of potassium peroxydisulfate and water-soluble monomer is 1:(100~500)；
Preferably, in polymerization process, pH is 3~5, and temperature is 70~85 DEG C, and the reaction time is 2~6h.
Excellent results of the invention are as follows:
1. raw material of the present invention is easy to get, process is simple and safe, and production cost is low.
2. with functional groups such as a large amount of hydroxyl, amino, amide groups in compound, therefore can polymerize with acrylic amide
Object generates good interaction, and then improves the performance steady in a long-term of polymer at high temperature.
3. the inorganic component with rigidity in compound, and the branched structure type polyethyleneimine amine component of rigidity, therefore,
Under reservoir conditions, Nanodispersion itself has good temperature-resistant anti-salt performance.
4. product of the present invention dissolution and dispersion performance it is excellent, powder product can simultaneously and acrylamide copolymer powder
It dissolves simultaneously, or is added in acrylamide copolymer solution and dissolves, it is easy to use.
5. product of the present invention post-processing is simple, continuous production easy to accomplish.
6. products of the present invention storage is convenient, meet the requirement in terms of environmental protection.
Detailed description of the invention
Fig. 1 is 1 polymer flooding experimental result of embodiment.
Specific embodiment
Experimental method used in following embodiments is conventional method unless otherwise specified.
The materials, reagents and the like used in the following examples is commercially available unless otherwise specified.
The present invention will be further described combined with specific embodiments below, but the scope of the present invention is not limited only to this.
Embodiment 1:
It is a kind of for improving the nano-complex of high temperature flooding polymers long-time stability, obtain as follows:
(1) polyethyleneimine-hectorite nanometer disperse system preparation
6g 2- acrylamide-2-methyl propane sulfonic is dissolved in 100mL water, 2g hectorite is then added, stirs 36h,
Prepare hectorite nanometer disperse system；2g polyethyleneimine (molecular weight 1800) is dissolved in 3mL water, polyethyleneimine is prepared
Amine aqueous solution；Polyethylenimine solution is added drop-wise in hectorite nanometer disperse system, is stirred when being added dropwise, control pH is 2, is added dropwise
Stirring 30min is finished, polyethyleneimine-hectorite nanometer disperse system is obtained；
(2) preparation of organic-inorganic nanocomposite object
The polyethyleneimine of above-mentioned preparation-hectorite nanometer disperse system and 5g acrylamide are added to equipped with stirring
In the wolf bottle of device, logical nitrogen pipe and thermometer, nitrogen 30min is stirred and is passed through, pH is controlled 4.5, and 20mg is then added
Potassium peroxydisulfate raises the temperature to 75 DEG C, reacts 4h, and NaOH solution is added by system pH and is adjusted to 9, constant temperature aging 1h will be produced
Object is dry, crushes to get nano-complex.
Embodiment 2:
As described in Example 1, except that 2- acrylamide-2-methyl propane sulfonic dosage is 8g.
Embodiment 3:
As described in Example 1, except that hectorite dosage is 3g.
Embodiment 4:
As described in Example 1, except that polyethyleneimine dosage is 3g.
Embodiment 5:
As described in Example 1, except that polyethyleneimine dosage is 1g.
Embodiment 6:
As described in Example 1, except that the molecular weight of polyethyleneimine is 4800.
Embodiment 7:
As described in Example 1, except that acrylamide dosage is 8g.
Embodiment 8:
As described in Example 1, except that nonionic water-soluble monomers are 5g vinyl pyrrolidone.
Embodiment 9:
As described in Example 1, except that nonionic water-soluble monomers are 1.5g vinyl pyrrolidone and 3.5g third
Acrylamide.
Embodiment 10:
As described in Example 1, except that nonionic water-soluble monomers be 1.5g vinyl pyrrolidone and 3.5g N,
N- dimethacrylamide.
Embodiment 11:
As described in Example 1, except that potassium peroxydisulfate dosage is 40mg.
Embodiment 12:
As described in Example 1, except that polymerization reaction pH is 3.5.
Performance evaluation
In order to investigate the ability that 1~12 product of embodiment promotes flooding polymers long-time stability, is tested, surveyed as follows
Examination carries out in simulation mineralized water, and ion concentration and total salinity are as shown in table 1, and experimental result is as shown in table 2.
The test of polymer solution apparent viscosity:
With mineralized water compound concentration be 0.2% flooding polymers solution (Tianjin Bo Hong petrochemical industry Co., Ltd,
BHKY-3), as a comparison case, being separately added into concentration in the comparative example is 0.01% embodiment 1~12, as embodiment solution.
By each sample solution age 90 days at 90 DEG C, with polymer solution before and after the test aging of Brookfield DV3T type viscosimeter
Viscosity, test revolving speed be 6r/min.
It can be seen from the results that embodiment has been obviously improved the thickening property of flooding polymers, before aging viscosity by
20.4mPas increases to 26.8~39.2mPas；Viscosity retention ratio after high temperature ageing also increases to 49.2% by 32.4%~
60.4%.
1 mineralized water of table composition
| Ion composition | Na+ | Ca2+ | Mg2+ | Cl- | Total mineral degree |
| Content (mg/L) | 9250 | 375 | 125 | 10250 | 20000 |
2 Evaluation results of table
| Sample number into spectrum | Initial viscosity (mPas) | Viscosity (mPas) after aging | Viscosity retention ratio |
| Embodiment 1 | 32.6 | 17.2 | 52.8% |
| Embodiment 2 | 36.1 | 18.2 | 50.4% |
| Embodiment 3 | 38.5 | 20.8 | 54.0% |
| Embodiment 4 | 39.2 | 19.3 | 49.2% |
| Embodiment 5 | 30.3 | 16.4 | 54.1% |
| Embodiment 6 | 30.9 | 16.2 | 52.4% |
| Embodiment 7 | 35.5 | 17.5 | 49.3% |
| Embodiment 8 | 26.8 | 16.2 | 60.4% |
| Embodiment 9 | 30.7 | 17.7 | 57.6% |
| Embodiment 10 | 29.8 | 17.5 | 58.7% |
| Embodiment 11 | 28.1 | 15.0 | 53.4% |
| Embodiment 12 | 31.8 | 16.9 | 53.1% |
| Comparative example 1 | 20.4 | 6.6 | 32.4% |
The polymer prepared using embodiment 1 after aging 90 days, carries out improving recovery ratio laboratory experiment, will be obtained poly-
The polymer solution that object is configured to 0.2% with mineralized water is closed, which is injected into (fill out sand tube sectional area in one-dimensional sandpack column
4.91cm2, length 30cm) and initial oil saturation is 75%, water drive to moisture content 98%, (crude oil used at 90 DEG C, shearing speed
Rate 7.34s-1Under the conditions of viscosity be 61.5mPas) injection rate is 1mL/min, after injecting the aqueous solutions of polymers of 0.35PV, after
Continuous water drive to moisture content reaches 98%, measures recovery ratio and improves 15.6%.
Claims (6)
1. it is a kind of for improving the nano-complex of high temperature flooding polymers long-time stability, it obtains as follows:
(1) polyethyleneimine-hectorite nanometer disperse system preparation
It disperses hectorite in 2- acrylamide-2-methyl propane sulfonic solution, stirs 24~48h, prepare hectorite nanometer point
The polyethylenimine solution that concentration is 100~600g/L is then added drop-wise in hectorite nanometer disperse system by granular media system, side drop
Edged stirring, and control pH be 1~6, be added dropwise stirring 30min to get；The molecular weight of polyethyleneimine be 300~
The concentration of 20000,2- acrylamide-2-methyl propane sulfonic solution is 10~150g/L, hectorite and 2- acrylamide -2- methyl
The mass ratio of propane sulfonic acid is 1:(2~8), the mass ratio of hectorite and polyethyleneimine is 1:(0.1~5)；
(2) preparation of organic-inorganic nanocomposite object
Polyethyleneimine-hectorite nanometer disperse system and nonionic water-soluble monomers are added to equipped with blender, logical nitrogen pipe
In the wolf bottle of thermometer, nitrogen 30min is stirred and is passed through, pH is controlled 2~6, and potassium peroxydisulfate is then added, will be warm
Degree is increased to 60~90 DEG C, reacts 1~10h, and end of reaction is added NaOH solution for system pH and is adjusted to 8~9, constant temperature aging 0.5
~1.5h, product is dry, crush to get；The mass ratio of 2- acrylamide-2-methyl propane sulfonic and nonionic water-soluble monomers
For 1:(0.1~5), the mass ratio of potassium peroxydisulfate and water-soluble monomer is 1:(100~1000)；
The nonionic water-soluble monomers are acrylamide, vinyl pyrrolidone, Methacrylamide, N- methylol propylene
Amide, N- ethyl acrylamide, N, N- dimethacrylamide, n-isopropyl acrylamide, hydroxy-ethyl acrylate, acrylic acid hydroxyl
One of propyl ester or two or more mixtures.
2. according to claim 1 for improving the nano-complex of high temperature flooding polymers long-time stability, feature
It is, the molecular weight of polyethyleneimine is 1000~5000 in step (1).
3. according to claim 1 for improving the nano-complex of high temperature flooding polymers long-time stability, feature
It is, the concentration of 2- acrylamide-2-methyl propane sulfonic solution is 25~100g/L in step (1), and polyethyleneimine amine concentration is
The mass ratio of 100~300g/L, hectorite and 2- acrylamide-2-methyl propane sulfonic is 1:(2~4), hectorite and polyethylene
The mass ratio of imines is 1:(0.2~2).
4. according to claim 1 for improving the nano-complex of high temperature flooding polymers long-time stability, feature
It is, polyethylenimine solution is added drop-wise in hectorite nanometer disperse system in step (1), and pH is 1~4.
5. according to claim 1 for improving the nano-complex of high temperature flooding polymers long-time stability, feature
Be, in step (2) mass ratio of 2- acrylamide-2-methyl propane sulfonic and nonionic water-soluble monomers be 1:(0.5~
1.5), the mass ratio of potassium peroxydisulfate and water-soluble monomer is 1:(100~500).
6. according to claim 1 for improving the nano-complex of high temperature flooding polymers long-time stability, feature
It is, in step (2) polymerization process, pH is 3~5, and temperature is 70~85 DEG C, and the reaction time is 2~6h.
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| CN111333792B (en) * | 2020-04-07 | 2022-09-16 | 中国石油大学(华东) | Modified nano hectorite anti-collapse agent and fluid loss additive as well as preparation method and application thereof |
| CN111648752A (en) * | 2020-04-29 | 2020-09-11 | 思达威(北京)能源科技有限公司 | Oil displacement monitoring method, application and oil field exploitation method |
| CN115677923B (en) * | 2022-10-26 | 2024-01-26 | 中海油田服务股份有限公司 | Pre-crosslinked gel particle plugging agent and preparation method and application thereof |
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| CN104357026A (en) * | 2014-05-30 | 2015-02-18 | 中国石油化工集团公司 | Treating agent for zwitter-ion inorganic-organic monomer polymer drilling fluid and preparation method of treating agent |
| CN105289553A (en) * | 2015-12-04 | 2016-02-03 | 中国石油大学(华东) | Method for preparing rapid high-efficiency absorbent used for heavy metal ions |
| CN105999283A (en) * | 2016-05-05 | 2016-10-12 | 东华大学 | Preparation method for adriamycin-loaded polyethyleneimine-hyaluronic acid-modified hectorite-coated gold nanoparticles |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104357026A (en) * | 2014-05-30 | 2015-02-18 | 中国石油化工集团公司 | Treating agent for zwitter-ion inorganic-organic monomer polymer drilling fluid and preparation method of treating agent |
| CN105289553A (en) * | 2015-12-04 | 2016-02-03 | 中国石油大学(华东) | Method for preparing rapid high-efficiency absorbent used for heavy metal ions |
| CN105999283A (en) * | 2016-05-05 | 2016-10-12 | 东华大学 | Preparation method for adriamycin-loaded polyethyleneimine-hyaluronic acid-modified hectorite-coated gold nanoparticles |
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