CN105384873A - Polynary high-molecular copolymer for oil extraction, and preparation method thereof - Google Patents
Polynary high-molecular copolymer for oil extraction, and preparation method thereof Download PDFInfo
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- CN105384873A CN105384873A CN201510915962.4A CN201510915962A CN105384873A CN 105384873 A CN105384873 A CN 105384873A CN 201510915962 A CN201510915962 A CN 201510915962A CN 105384873 A CN105384873 A CN 105384873A
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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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/36—Amides or imides
- C08F222/38—Amides
- C08F222/385—Monomers containing two or more (meth)acrylamide groups, e.g. N,N'-methylenebisacrylamide
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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
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
Abstract
A polynary high-molecular copolymer for oil extraction is characterized in that the copolymer is prepared through polymerizing the following monomers, by weight, 15-20 parts of acrylic acid, 10-15 parts of 2-acrylamido-2-methylpropanesulfonic acid, 20-30 parts of N,N'-methylenebisacrylamide and 12-22 parts of dimethyl-diallylammonium chloride, and the copolymer also comprises 0.3-1 part of a surfactant, 1.2-5 parts of tween 80, 0.2-0.5 parts of an initiator, 0.1-0.5 parts of a reaction promoter, 0.1-1 part of a chain transfer agent, 0.05-0.08 parts of a cross-linking inhibitor and a pH adjusting agent. The polynary high-molecular copolymer reduces sensitivity of molecules to high valence metal ions and inhibits amido group hydrolysis, so the copolymer has very strong temperature resistance; and AESO is mixed HABS to opposite generation of the surfactant insoluble in water, so the copolymer has very strong salt resistance.
Description
Technical field
The present invention relates to the displacement of reservoir oil multipolymer of oil recovery, be specifically related to a kind of oil recovery multicomponent high molecular multipolymer and preparation method thereof.
Background technology
Tertiary oil recovery is one of major measure improving oil recovery factor, and wherein polymer flooding oil process occupies critical role.Polymer oil-displacing agent is roughly divided into two large classes, i.e. natural polymer and artificial-synthetic copolymer.The mainly partially hydrolyzed polyacrylamide (HPAM) of a large amount of use at present and biological xanthan gum (Xanthan), wherein based on HPAM.HPAM is a kind of anionic polyelectrolyte, and the effect molecular chain because of electrostatic repulsion in fresh water presents the state comparatively stretched, and hydrodynamic volume is comparatively large, and tackifying ability is better.But, carboxyl on HPAM molecular chain is extremely responsive to salt, especially be easily separated when running into high volence metal ion, HPAM is facile hydrolysis when high temperature (temperature > 70 DEG C), after hydrolysis, in the oil reservoir that salinity is higher, normal generation is separated, and precipitation is formed to be accelerated, and causes solution viscosity significantly to reduce, thus HPAM does not possess the characteristic of temperature resistant antisalt, and may cause reservoir choke and injure stratum; And thermooxidative degradation can occur xanthan gum in high-temperature stratum, it is generally acknowledged the oil reservoir that can only be used in less than 60 DEG C, and xanthan gum anti-microbe ability is poor, expensive.
In order to obtain the good copolymer product of temperature resistant antisalt performance, current many experts and scholars have carried out a large amount of research work.Start with from the reason analyzing HPAM temperature resistant antisalt performance difference, reduce HPAM molecular chain curling, reduce molecule to the sensitivity of high volence metal ion, suppress amide group hydrolysis.Main solution one is and the function monomer copolymerization with temperature resistant antisalt performance structural unit, prepares temperature resistant antisalt multipolymer; Two is the hydrogen bond, statcoulomb power and the hydrophobic association equimolecular intermolecular forces that utilize between macro-radical, carries out Macromolecular self-assembly.Many investigators expand large quantifier elimination, set about from the thinking of Molecular Structure Design, the Heat Resistant and Salt Tolerant Polymer product such as multipolymer of design and synthesis multiplexed combination multipolymer, hydrophobic associated water-soluble polymer, amphoteric ion polymer and new molecular architecture.
Patent CN1814637A discloses a kind of preparation method of temperature-tolerant anti-salt polyacrylamide, introduce three kinds of heat-resistant salt-resistant monomers and acrylamide copolymerization, synthesize acrylamide/2-acrylamide-2-methylpro panesulfonic acid/methacrylic acid/dimethyl diallyl ammonium chloride tetrapolymer, the heat-resistant salt-resistant multipolymers such as acrylamide/2-acrylamide and-2-methyl propane sulfonic acid/methylene-succinic acid/acrylyl oxy-ethyl-trimethyl salmiac tetrapolymer, the heat-resistant salt-resistant performance of the product that these polymkeric substance improve really, but salinity can only be met lower than 10000mg/L, temperature is lower than under the condition of 65 DEG C, the application demand under higher temperature and salinity condition can not be met.
Summary of the invention
The present invention, in order to solve the shortcoming of polymkeric substance in heat-resistant salt-resistant performance in oil field, provides a kind of oil recovery multicomponent high molecular multipolymer and preparation method thereof.
Technical scheme of the present invention is a kind of oil recovery multicomponent high molecular multipolymer, it is characterized in that: formed by the monomer polymerization of following parts by weight: 15 ~ 20 parts, vinylformic acid, 2-acrylamide-2-methylpro panesulfonic acid 10 ~ 15 parts, N, N '-methylene-bisacrylamide 20 ~ 30 parts, dimethyl-diallyl ammonium chloride 12 ~ 22 parts; Also comprise following auxiliary: 0.3 ~ 1 part, tensio-active agent, tween 80 1.2 ~ 5 parts, initiator 0.2 ~ 0.5 part, reaction promotor 0.1 ~ 0.5 part, chain-transfer agent 0.1 ~ 1 part, anti-linking agent 0.05 ~ 0.08 part, pH adjusting agent;
Described tensio-active agent is the mixture of aliphatic alcohol polyoxyethylene sulfonate (AESO) and heavy alkylbenzene sulfonate (HABS);
Described initiator is oxidation/azo or Potassium Persulphate;
Described reaction promotor organic amine or thiazole compound;
Described chain-transfer agent is propylene glycol or butyleneglycol;
Described anti-linking agent is urea or thiocarbamide;
N, N '-methylene-bisacrylamide has symmetrical amide structure, the polymkeric substance ratio formed after being polymerized with vinylformic acid, 2-acrylamide-2-methylpro panesulfonic acid, dimethyl-diallyl ammonium chloride before polymkeric substance disclosed in prior art increases intermolecular hydrogen bond action, Supramolecular self assembly structure can be formed under finite concentration in aqueous, reduce HPAM molecular chain curling, reduce molecule to the sensitivity of high volence metal ion, suppress amide group hydrolysis.
Further, the weight ratio of described tensio-active agent aliphatic alcohol polyoxyethylene sulfonate (AESO) and heavy alkylbenzene sulfonate (HABS) is 2:8, with S-WAT/sodium bisulfite mixture for sulphonating agent, react with AES under high temperature, condition of high voltage, generate alkyl polyoxyethylene ether sulfonate (AESO), wider, cheap, the superior performance in heavy alkylbenzene sulfonate (HABS) source; Sulfonate ion in HABS calcium ions and magnesium ions in water is combined, and generates water-fast ionogenic surfactant, and the surfactant concentration causing water-oil interface to adsorb declines, and oil water interfacial tension raises; In AESO, sulfonate ion calcium ions and magnesium ions in water is combined, and also make sulfonate radical in AESO molecule water insoluble, but in AESO molecule, polyoxyethylene group is very well water-soluble, and can contend with water-fast tensio-active agent generation.
Further, the molecular weight ranges of described multipolymer is 1000 ~ 3,000 ten thousand.
Prepare a method for oil recovery multicomponent high molecular polymkeric substance as claimed in claim 1, it is characterized in that:
(1) by the monomeric acrylic 15 ~ 20 parts of following components by weight percent, 2-acrylamide-2-methylpro panesulfonic acid 10 ~ 15 parts, N, N '-methylene-bisacrylamide 20 ~ 30 parts, dimethyl-diallyl ammonium chloride 12 ~ 22 parts are soluble in water, be mixed with the aqueous solution, in obtained aqueous solution, the volumetric molar concentration of each monomer component is: vinylformic acid 0.2 ~ 0.28mol/L, 2-acrylamide-2-methylpro panesulfonic acid 0.045 ~ 0.072mol/L, N, N '-methylene-bisacrylamide 0.12 ~ 0.19mol/L, dimethyl-diallyl ammonium chloride 0.07 ~ 0.13mol/L; Add the pH value of pH adjusting agent regulator solution to 9;
(2) in step (1) obtained aqueous solution, initiator is added, parts by weight are 0.2 ~ 0.5 part, then 70 ~ 90 DEG C are warming up to, add anti-linking agent 0.05 ~ 0.08 part, reaction promotor 0.1 ~ 0.5 part, react 3.5 ~ 4.5 hours, then add chain-transfer agent 0.1 ~ 1 part, Temperature fall is to room temperature;
(3) polymkeric substance that step (2) obtains is added 0.3 ~ 1 part, tensio-active agent, tween 80 1.2 ~ 5 parts, mixing speed is 3000r/min, time 1 ~ 3min, then obtains multicomponent high molecular polymkeric substance according to claim 1.
Wherein, the weight ratio of described tensio-active agent aliphatic alcohol polyoxyethylene sulfonate (AESO) and heavy alkylbenzene sulfonate (HABS) is 2:8.
Wherein, the molecular weight ranges of described multipolymer is 1000 ~ 3,000 ten thousand.
Beneficial effect of the present invention is: 1, poly-molecular polymer of the present invention, monomer comprises N, N '-methylene-bisacrylamide, N, N '-methylene-bisacrylamide has symmetrical amide structure, with vinylformic acid, 2-acrylamide-2-methylpro panesulfonic acid, the polymkeric substance ratio formed after dimethyl-diallyl ammonium chloride polymerization before polymkeric substance disclosed in prior art increases intermolecular hydrogen bond action, Supramolecular self assembly structure can be formed in aqueous under finite concentration, reduce the curling of HPAM molecular chain, reduce molecule to the sensitivity of high volence metal ion, suppress amide group hydrolysis, whole polymkeric substance is made to have very strong temperature tolerance,
2, tensio-active agent is made up of aliphatic alcohol polyoxyethylene sulfonate (AESO) and heavy alkylbenzene sulfonate (HABS) mixing, in AESO molecule, polyoxyethylene group is very well water-soluble, can be contended with water-fast tensio-active agent generation, makes whole polymkeric substance have very strong salt tolerance.
Embodiment
By the following examples the present invention is specifically described.
Embodiment one: by the monomeric acrylic 15 parts of following components by weight percent, 2-acrylamide-2-methylpro panesulfonic acid 10 parts, N, N '-methylene-bisacrylamide 30 parts, dimethyl-diallyl ammonium chloride 20 parts are dissolved in the water of 1000 parts, be mixed with the aqueous solution, in obtained aqueous solution, the volumetric molar concentration of each monomer component is: vinylformic acid 0.2mol/L, 2-acrylamide-2-methylpro panesulfonic acid 0.045mol/L, N, N '-methylene-bisacrylamide 0.12mol/L, dimethyl-diallyl ammonium chloride 0.07mol/L; Add the pH value of pH adjusting agent (sodium carbonate or salt of wormwood) regulator solution to 9; Initiator azo-bis-isobutyrate hydrochloride (AIBA) is added in step (1) obtained aqueous solution, parts by weight are 0.2 part, then 70 DEG C are warming up to, add 0.05 part, anti-linking agent urea, reaction promotor triethylene diamine 0.3 part, react 4 hours, then add chain-transfer agent propylene glycol 0.5 part, Temperature fall is to room temperature; The polymkeric substance that step (2) obtains is added 0.3 part, tensio-active agent (AESO:HABS=2:8), tween 80 1.2 parts, mixing speed is 3000r/min, time 1min, then obtain multicomponent high molecular polymkeric substance according to claim 1, the molecular weight ranges of the multipolymer obtained is 1000 ~ 3,000 ten thousand.
Embodiment two: by the monomeric acrylic 20 parts of following components by weight percent, 2-acrylamide-2-methylpro panesulfonic acid 15 parts, N, N '-methylene-bisacrylamide 20 parts, dimethyl-diallyl ammonium chloride 12 parts are dissolved in the water of 1000 parts, be mixed with the aqueous solution, in obtained aqueous solution, the volumetric molar concentration of each monomer component is: vinylformic acid 0.28mol/L, 2-acrylamide-2-methylpro panesulfonic acid 0.072mol/L, N, N '-methylene-bisacrylamide 0.19mol/L, dimethyl-diallyl ammonium chloride 0.11mol/L; Add the pH value of pH adjusting agent (sodium carbonate or salt of wormwood) regulator solution to 9; Initiator azo-bis-isobutyrate hydrochloride (AIBA) is added in step (1) obtained aqueous solution, parts by weight are 0.2 part, then 70 DEG C are warming up to, add 0.05 part, anti-linking agent urea, reaction promotor triethylene diamine 0.3 part, react 4 hours, then add chain-transfer agent propylene glycol 0.5 part, Temperature fall is to room temperature; The polymkeric substance that step (2) obtains is added 0.3 part, tensio-active agent (AESO:HABS=2:8), tween 80 1.2 parts, mixing speed is 3000r/min, time 1min, then obtain multicomponent high molecular polymkeric substance according to claim 1, the molecular weight ranges of the multipolymer obtained is 1000 ~ 3,000 ten thousand.
Embodiment three: by the monomeric acrylic 18 parts of following components by weight percent, 2-acrylamide-2-methylpro panesulfonic acid 12 parts, N, N '-methylene-bisacrylamide 25 parts, dimethyl-diallyl ammonium chloride 18 parts are dissolved in the water of 1000 parts, be mixed with the aqueous solution, in obtained aqueous solution, the volumetric molar concentration of each monomer component is: vinylformic acid 0.25mol/L, 2-acrylamide-2-methylpro panesulfonic acid 0.060mol/L, N, N '-methylene-bisacrylamide 0.15mol/L, dimethyl-diallyl ammonium chloride 0.096mol/L; Add the pH value of pH adjusting agent (sodium carbonate or salt of wormwood) regulator solution to 9; Initiator azo-bis-isobutyrate hydrochloride (AIBA) is added in step (1) obtained aqueous solution, parts by weight are 0.2 part, then 70 DEG C are warming up to, add 0.05 part, anti-linking agent urea, reaction promotor triethylene diamine 0.3 part, react 4 hours, then add chain-transfer agent propylene glycol 0.5 part, Temperature fall is to room temperature; The polymkeric substance that step (2) obtains is added 0.3 part, tensio-active agent (AESO:HABS=2:8), tween 80 1.2 parts, mixing speed is 3000r/min, time 1min, then obtain multicomponent high molecular polymkeric substance according to claim 1, the molecular weight ranges of the multipolymer obtained is 1000 ~ 3,000 ten thousand.
Comparative example: with reference to a kind of oil field of patent of invention embodiment in heat-resistant salt-resistant multipolymer and preparation method thereof (CN102372818B), the preparation method of embodiment one:
The N,N-DMAA of the acrylamide of 69.3 parts and 5.7 parts is dissolved in 422 parts of water, makes acrylamide and the total massfraction of N,N-DMAA two kinds of monomers be 15%; Reconcile pH value to 8 ~ 10 with 2 parts of sodium hydroxide solutions, pour monomer solution into reaction vessel, make bath temperature be 5 DEG C, logical nitrogen deoxygenation 30 minutes; Then 0.003% composite initiation system is added: the potassium persulfate solution 0.23 part of 0.15%, the sodium sulfite solution 0.13 part of 0.09%, 0.6% methacrylic acid N, N-dimethylaminoethyl 0.3 part; React after 30 minutes, be warmed up to 30 DEG C, continue constant temperature polyreaction after 4 hours, stopped reaction, by the colloidal product obtained, add the sodium hydroxide solution 157.6g that concentration is 5%, at 80 DEG C, be hydrolyzed 1 hour, then vacuum-drying, pulverizes, namely obtains heat-resistant salt-resistant multipolymer KWKY-PAD.
Reaching about 20000mg/L (wherein calcium ions and magnesium ions concentration is greater than 500mg/L) in salinity, under high temperature and high salinity condition that temperature reaches more than 65 DEG C, each performance perameter of product obtained in testing example, as following table:
| Sequence number | Degree of hydrolysis/% | Molecular weight | Apparent viscosity/mPas | Viscosity retention ratio/% |
| Embodiment 1 | 5.2 | 1742 ten thousand | 19.3 | 90.2 |
| Embodiment 2 | 7.1 | 1997 ten thousand | 18.8 | 89.8 |
| Embodiment 3 | 5.5 | 2010 ten thousand | 19.8 | 92.1 |
| Comparative example | 14.3 | 1200 ten thousand | 12.1 | 71.2 |
| Commercially available HAMP | 48.3 | 2800 | 6.9 | 26.2 |
Degree of hydrolysis: test by GB/T12005.6-89 partially hydrolyzed polyacrylamide degree of hydrolysis measuring method;
Molecular weight: measure (viscosimetry) by GB/T12005.10-92 Molecular Weight for Polyacrylamide and measure intrinsic viscosity, and calculate by [η]=3.73 × 10-4Mw0.66;
Apparent viscosity: at 95 DEG C, salt solution total mineralization 45073mg/L, Ca
2++ Mg
2+: 1500mg/L polymer concentration solution under 1956mg/L, adopts Brookfield viscometer, shearing rate 7.34s
-1lower test;
Viscosity retention ratio: salt solution total mineralization 45073mg/L, Ca
2++ Mg
2+: under 1956mg/L, 1500mg/L polymer concentration solution constant temperature at 95 DEG C is after aging 30 days, adopts Brookfield viscometer, shearing rate 7.34s
-1lower test.
Above one embodiment of the present of invention have been described in detail, but described content being only preferred embodiment of the present invention, can not being considered to for limiting practical range of the present invention.All equalizations done according to the present patent application scope change and improve, and all should still belong within patent covering scope of the present invention.
Claims (6)
1. multicomponent high molecular multipolymer is used in an oil recovery, it is characterized in that: formed by the monomer polymerization of following parts by weight: 15 ~ 20 parts, vinylformic acid, 2-acrylamide-2-methylpro panesulfonic acid 10 ~ 15 parts, N, N '-methylene-bisacrylamide 20 ~ 30 parts, dimethyl-diallyl ammonium chloride 12 ~ 22 parts; Also comprise following auxiliary: 0.3 ~ 1 part, tensio-active agent, tween 80 1.2 ~ 5 parts, initiator 0.2 ~ 0.5 part, reaction promotor 0.1 ~ 0.5 part, chain-transfer agent 0.1 ~ 1 part, anti-linking agent 0.05 ~ 0.08 part, pH adjusting agent;
Described tensio-active agent is the mixture of aliphatic alcohol polyoxyethylene sulfonate (AESO) and heavy alkylbenzene sulfonate (HABS);
Described initiator is oxidation/azo or Potassium Persulphate;
Described reaction promotor organic amine or thiazole compound;
Described chain-transfer agent is propylene glycol or butyleneglycol;
Described anti-linking agent is urea or thiocarbamide.
2. a kind of oil recovery multicomponent high molecular multipolymer according to claim 1, is characterized in that: the weight ratio of described tensio-active agent aliphatic alcohol polyoxyethylene sulfonate (AESO) and heavy alkylbenzene sulfonate (HABS) is 2:8.
3. a kind of oil recovery multicomponent high molecular multipolymer according to claim 1, is characterized in that: the molecular weight ranges of described multipolymer is 1000 ~ 3,000 ten thousand.
4. prepare a method for oil recovery multicomponent high molecular polymkeric substance as claimed in claim 1, it is characterized in that:
(1) by the monomeric acrylic 15 ~ 20 parts of following components by weight percent, 2-acrylamide-2-methylpro panesulfonic acid 10 ~ 15 parts, N, N '-methylene-bisacrylamide 20 ~ 30 parts, dimethyl-diallyl ammonium chloride 12 ~ 22 parts are soluble in water, be mixed with the aqueous solution, in obtained aqueous solution, the volumetric molar concentration of each monomer component is: vinylformic acid 0.2 ~ 0.28mol/L, 2-acrylamide-2-methylpro panesulfonic acid 0.045 ~ 0.072mol/L, N, N '-methylene-bisacrylamide 0.12 ~ 0.19mol/L, dimethyl-diallyl ammonium chloride 0.07 ~ 0.13mol/L; Add the pH value of pH adjusting agent regulator solution to 9;
(2) in step (1) obtained aqueous solution, initiator is added, parts by weight are 0.2 ~ 0.5 part, then 70 ~ 90 DEG C are warming up to, add anti-linking agent 0.05 ~ 0.08 part, reaction promotor 0.1 ~ 0.5 part, react 3.5 ~ 4.5 hours, then add chain-transfer agent 0.1 ~ 1 part, Temperature fall is to room temperature;
(3) polymkeric substance that step (2) obtains is added 0.3 ~ 1 part, tensio-active agent, tween 80 1.2 ~ 5 parts, mixing speed is 3000r/min, time 1 ~ 3min, then obtains multicomponent high molecular polymkeric substance according to claim 1.
5. a kind of method preparing oil recovery multicomponent high molecular polymkeric substance as claimed in claim 1 according to claim 4, is characterized in that: the weight ratio of described tensio-active agent aliphatic alcohol polyoxyethylene sulfonate (AESO) and heavy alkylbenzene sulfonate (HABS) is 2:8.
6. a kind of method preparing oil recovery multicomponent high molecular polymkeric substance as claimed in claim 1 according to claim 4, is characterized in that: the molecular weight ranges of described multipolymer is 1000 ~ 3,000 ten thousand.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112279962A (en) * | 2019-07-25 | 2021-01-29 | 中国石油化工股份有限公司 | Terpolymer used as thick oil displacement agent and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1814637A (en) * | 2005-01-31 | 2006-08-09 | 大连广汇化学有限公司 | Method for preparing temperature-resistant and anti-salt type polyacrylamide |
| CN101935522A (en) * | 2010-08-18 | 2011-01-05 | 江南大学 | Preparation of long-chain alkyl acyl benzene sulfonic acid sodium salt and application thereof in enhancing oil recovery rate |
-
2015
- 2015-12-09 CN CN201510915962.4A patent/CN105384873A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1814637A (en) * | 2005-01-31 | 2006-08-09 | 大连广汇化学有限公司 | Method for preparing temperature-resistant and anti-salt type polyacrylamide |
| CN101935522A (en) * | 2010-08-18 | 2011-01-05 | 江南大学 | Preparation of long-chain alkyl acyl benzene sulfonic acid sodium salt and application thereof in enhancing oil recovery rate |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112279962A (en) * | 2019-07-25 | 2021-01-29 | 中国石油化工股份有限公司 | Terpolymer used as thick oil displacement agent and preparation method thereof |
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