CN116004216B - Ammonium salt composite complexing agent for fracturing and preparation method thereof - Google Patents
Ammonium salt composite complexing agent for fracturing and preparation method thereof Download PDFInfo
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Abstract
The invention belongs to the technical field of oilfield exploitation, and particularly relates to an ammonium salt composite complexing agent for fracturing and a preparation method thereof. The ammonium salt compound complexing agent for fracturing consists of a main agent and an auxiliary agent, wherein the auxiliary agent is an aqueous solution of a neutralization product of polycarboxylic acid and ammonia water, and the molecular structural formula of the main agent is as follows:
Description
Technical Field
The invention belongs to the technical field of oilfield exploitation, and particularly relates to an ammonium salt composite complexing agent for fracturing and a preparation method thereof.
Background
The exploitation difficulty of the oil field is increased gradually in the middle and later stages of exploitation. Unconventional oil and gas reservoirs are important directions of production increase, and the oil and gas reservoirs generally have the characteristics of deep burial, low permeability, high temperature and the like, and the fracturing reformation of the oil and gas reservoirs is an effective production increase measure. However, in the process of transformation, clay can absorb water into a crystal structure when meeting water, so that the volume of the clay is increased, thereby blocking stratum pore passages, clay substances are dispersed by external liquid or carried by produced liquid in the further migration process, bridge resistance or throttling points are formed at pore throats of capillaries, stratum pore passages are easily blocked, and then the permeability of the stratum is reduced, so that the production of an oil well is reduced. Therefore, an anti-swelling stabilizer must be added to the fracturing fluid to protect the formation from damage.
The mechanism of the anti-swelling stabilizer for protecting the stratum from damage is as follows: forming a hydrophobic surface on the clay surface, isolating the dipole of silicon oxygen bond or hydrogen oxygen bond of the clay crystal face to attract water molecules, thereby playing a role in preventing the hydration and expansion of the clay; and then the solution is utilized to generate ion rejection and polymerization condensation in a hydrated clay system, so that clay minerals are coalesced under the action of the intermolecular force, and the effect of preventing the dispersion and migration of clay is achieved.
The common inorganic salt anti-swelling agent has low price, but has large dosage and short action time, and can increase the mineralization degree of the water body.
CN101921366 discloses a clay anti-swelling agent for oil extraction and its preparation method, according to mass percentage, 50-90% diallyl ammonium chloride monomer and 10-50% triallyl amine monomer are dissolved in distilled water, the total mass percentage concentration of the two monomers is 20-80%, nitrogen is introduced into a reaction kettle, at 65-85 ℃, initiator is added, the initiator is ammonium persulfate, potassium persulfate or hydrogen peroxide, and the reaction is carried out for 4-6 hours, thus obtaining the clay anti-swelling agent for oil extraction with a polymer having a molecular structure of three branched chains and containing organic cations; the swelling inhibitor has strong clay inhibition, lasting swelling preventing effect, water flow scouring resistance and no damage to stratum, and can be used in water injection, acidification and well control fluid. However, the product of the patent is a polymer composition, has larger molecular weight, and is easy to form plugs in stratum pore passages, thereby blocking the stratum and affecting development.
Disclosure of Invention
The invention provides an ammonium salt composite complexing agent for fracturing and a preparation method thereof, aiming at the defects of the prior art. The ammonium salt compound complexing agent has the advantages of wide raw material sources and simple synthesis process; the anti-swelling effect is good; water-resistant.
The first object of the invention discloses an ammonium salt composite complexing agent for fracturing, which consists of a main agent and an auxiliary agent, wherein the auxiliary agent is an aqueous solution of a neutralization product of polycarboxylic acid and ammonia water, and the molecular structural formula of the main agent is as follows:
preferably, the polycarboxylic acid is one of malic acid, citric acid, nitrilotriacetic acid and ethylenediamine tetraacetic acid; more preferably, the polycarboxylic acid is nitrilotriacetic acid or ethylenediamine tetraacetic acid.
Preferably, the mass ratio of the main agent to the auxiliary agent is 1:5-8.
The invention further discloses a preparation method of the ammonium salt composite complexing agent for fracturing, which comprises the following specific steps:
(1) Preparation of the Main agent
Adding 1,4 cyclohexanedione, 1-methylpiperazine and 20wt% formic acid aqueous solution into a high-pressure reaction kettle, heating to 180-190 ℃, carrying out heat preservation reaction, cooling to below 40 ℃ after the reaction is finished, extracting with chloroform, and carrying out reduced pressure distillation to obtain viscous liquid; dissolving the viscous liquid with an organic solvent, transferring to a four-neck flask, adding dodecyl bromide, heating for reflux reaction, and distilling under reduced pressure to obtain a viscous solid which is a main agent crude product after the reaction is finished; recrystallizing the main agent crude product with ethyl acetate, and drying at 105 ℃ for 4-6h to obtain the main agent.
(2) Preparation of side agent
The polycarboxylic acid and 10wt% ammonia water are mixed and dissolved uniformly according to a certain molar ratio to obtain the side agent.
(3) Preparation of the product
And uniformly mixing and dissolving the main agent and the auxiliary agent to obtain the ammonium salt composite complexing agent for fracturing.
Preferably, in the step (1), the 1-methylpiperazine, formic acid and dodecyl bromide are used in an amount of 1.8 to 2.2 molar parts, 2 to 4 molar parts and 3.2 to 4 molar parts, respectively, based on 1 molar part of 1,4 cyclohexanedione; more preferably, the 1-methylpiperazine, formic acid, dodecyl bromide are used in an amount of 1.9 to 2.1 mole parts, 3 to 4 mole parts, 3.4 to 3.8 mole parts, respectively, based on 1 mole part of 1,4 cyclohexanedione.
Preferably, in the step (1), the incubation time is 12-24 hours.
Preferably, in the step (1), the mass ratio of chloroform to 1,4 cyclohexanedione is 5-10:1.
preferably, in the step (1), the organic solvent is one of ethanol, propanol, isopropanol, butanol and isobutanol, and more preferably one of ethanol and isobutanol.
Preferably, in the step (1), the mass ratio of the organic solvent to the 1,4 cyclohexanedione is 50 to 60:1.
preferably, in the step (1), the heating reflux reaction time is 24-48h.
Preferably, in the step (1), the mass ratio of the ethyl acetate to the 1,4 cyclohexanedione is 30-40:1.
preferably, in the step (2), the polycarboxylic acid is one of malic acid, citric acid, nitrilotriacetic acid and ethylenediamine tetraacetic acid; more preferably, it is one of nitrilotriacetic acid and ethylenediamine tetraacetic acid.
Preferably, in the step (2), the molar ratio of the polycarboxylic acid to 10wt% of aqueous ammonia is 1:2-4.
Preferably, in the step (3), the mass ratio of the main agent to the auxiliary agent is 1:5-8.
The reaction equation for synthesizing the main agent of the ammonium salt compound complexing agent is as follows:
the invention relates to an ammonium salt compound complexing agent for fracturing, which consists of a main agent and an auxiliary agent. Each molecule of the main agent contains 4 quaternary ammonium cations, the quaternary ammonium cations can enable negative charges on the surface of clay to be adsorbed and neutralized, repulsive force between crystal layers is reduced, and clay particles are prevented from being moved due to electrostatic repulsive force, so that an anti-swelling effect is achieved, each molecule contains 4 dodecyl groups which are hydrophobic groups, the surface of clay is changed from hydrophilic to lipophilic after adsorption, infiltration of water molecules to clay particles can be effectively prevented, and hydration swelling of clay is controlled; the auxiliary agents are all ammonium salts of polybasic acid, the radius of ammonium ions is 286pm, the auxiliary agents are very close to the structural holes 280pm of clay, the auxiliary agents are easy to enter the hole spaces and are not easy to release, and the combination is firm. The quaternary ammonium salt and ammonium ions can lead the product molecules to be complexly adsorbed on the exchange points of the clay in a network form, and are adsorbed on the surface of the clay through the actions of intermolecular force, hydrogen bond force and the like, thereby preventing the damage to hydrocarbon reservoirs caused by hydration expansion and dispersion migration of water-sensitive minerals in a hypotonic reservoir.
Compared with the prior art, the invention has the following advantages and beneficial effects:
(1) The ammonium salt composite complexing agent for fracturing is liquid, consists of a main agent and an auxiliary agent, wherein the main agent is solid, the auxiliary agent is liquid, and the raw materials are widely available and the synthesis and preparation process is simple;
(2) The ammonium salt composite complexing agent for fracturing is convenient to use, small in dosage and high in oil reservoir adaptability, and can meet the development requirement of oil fields;
(3) The ammonium salt compound complexing agent for fracturing has the advantage of high anti-swelling rate, the anti-swelling rate reaches more than 90% under the condition of using the concentration of 2wt%, and the anti-swelling rate can reach more than 80% after washing.
Detailed Description
The endpoints and any values of the ranges disclosed herein are not limited to the precise range or value, and are understood to encompass values approaching those ranges or values. For numerical ranges, one or more new numerical ranges may be found between the endpoints of each range, between the endpoint of each range and the individual point value, and between the individual point value, in combination with each other, and are to be considered as specifically disclosed herein.
Example 1 (1) preparation of Main agent
0.05mol of 1,4 cyclohexanedione, 0.09mol of 1-methylpiperazine and 0.1mol of 20wt% formic acid water solution are added into a high-pressure reaction kettle, the temperature is raised to 180 ℃, the reaction is kept for 12 hours, after the reaction is completed, the temperature is reduced to below 40 ℃, the chloroform is used for extraction, and the viscous liquid is obtained through reduced pressure distillation.
The viscous liquid is dissolved by 280g of propanol and transferred into a four-necked flask, 0.16mol of dodecyl bromide is added, the mixture is heated and refluxed for 24 hours, and after the reaction is finished, the viscous solid is obtained by reduced pressure distillation, and is a main agent crude product.
The main agent crude product is recrystallized by 168g of ethyl acetate and dried for 4 hours at 105 ℃ to obtain the main agent.
(2) Preparation of side agent
1mol of malic acid and 2mol of 10wt% ammonia water are mixed and dissolved uniformly to obtain the side agent.
(3) Preparation of the product
Mixing and dissolving 10g of main agent and 80g of auxiliary agent uniformly to obtain the ammonium salt compound complexing agent L for fracturing 1 。
Example 2 (1) preparation of Main agent
0.05mol of 1,4 cyclohexanedione, 0.11mol of 1-methylpiperazine and 0.12mol of 20wt% formic acid water solution are added into a high-pressure reaction kettle, the temperature is raised to 190 ℃, the reaction is kept for 16 hours, after the reaction is completed, the temperature is reduced to below 40 ℃, the chloroform is used for extraction, and the reduced pressure distillation is carried out, so that viscous liquid is obtained.
The viscous liquid is dissolved by 336g of butanol, transferred into a four-necked flask, added with 0.2mol of dodecyl bromide, heated and refluxed for 48 hours, and distilled under reduced pressure after the reaction is finished to obtain a viscous solid which is a main agent crude product.
The crude product of the main agent is recrystallized by 178g of ethyl acetate and dried for 6 hours at 105 ℃ to obtain the main agent.
(2) Preparation of side agent
1mol of citric acid and 3mol of 10wt% ammonia water are mixed and dissolved uniformly to obtain the side agent.
(3) Preparation of the product
Mixing and dissolving 10g of main agent and 75g of auxiliary agent uniformly to obtain the ammonium salt compound complexing agent L for fracturing 2 。
EXAMPLE 3 preparation of the Main agent (1)
0.05mol of 1,4 cyclohexanedione, 0.092mol of 1-methylpiperazine and 0.14mol of 20wt% formic acid water solution are added into a high-pressure reaction kettle, the temperature is raised to 182 ℃, the reaction is kept for 15 hours, after the reaction is finished, the temperature is reduced to below 40 ℃, the chloroform is used for extraction, and the reduced pressure distillation is carried out, so that viscous liquid is obtained.
The viscous liquid is dissolved by 295g of propanol and transferred into a four-necked flask, 0.17mol of dodecyl bromide is added, the mixture is heated and refluxed for 28 hours, and after the reaction is finished, the viscous solid is obtained by reduced pressure distillation and is a main agent crude product.
The above crude main agent was recrystallized from 189g of ethyl acetate and dried at 105℃for 5 hours to obtain a main agent.
(2) Preparation of side agent
1mol of nitrilotriacetic acid and 3mol of 10wt% ammonia water are mixed and dissolved uniformly to obtain the side agent.
(3) Preparation of the product
Mixing and dissolving 10g of main agent and 70g of auxiliary agent uniformly to obtain the ammonium salt compound complexing agent L for fracturing 3 。
Example 4 (1) preparation of Main agent
0.05mol of 1,4 cyclohexanedione, 0.105mol of 1-methylpiperazine and 0.15mol of 20wt% formic acid water solution are added into a high-pressure reaction kettle, the temperature is raised to 185 ℃, the reaction is kept for 24 hours, after the reaction is completed, the temperature is reduced to below 40 ℃, 31g of chloroform is used for extraction, and the viscous liquid is obtained through reduced pressure distillation.
The viscous liquid is dissolved by 296g of propanol and transferred into a four-necked flask, 0.192mol of dodecyl bromide is added, the mixture is heated and refluxed for 36 hours, and after the reaction is finished, the viscous solid is obtained by reduced pressure distillation and is a main agent crude product.
The main agent crude product is recrystallized by 192g of ethyl acetate and dried for 4 hours at 105 ℃ to obtain the main agent.
(2) Preparation of side agent
1mol of ethylenediamine tetraacetic acid and 4mol of 10wt% ammonia water are mixed and dissolved uniformly to obtain the auxiliary agent.
(3) Preparation of the product
Mixing and dissolving 10g of main agent and 65g of auxiliary agent uniformly to obtain the ammonium salt compound complexing agent L for fracturing 4 。
EXAMPLE 5 preparation of the Main agent (1)
0.05mol of 1,4 cyclohexanedione, 0.095mol of 1-methylpiperazine and 0.17mol of 20wt% formic acid water solution are added into a high-pressure reaction kettle, the temperature is raised to 186 ℃, the reaction is kept for 18 hours, after the reaction is finished, the temperature is reduced to below 40 ℃, the chloroform is used for extraction, and the reduced pressure distillation is carried out, so that viscous liquid is obtained.
The viscous liquid is dissolved by 313g of isobutanol, transferred into a four-necked flask, added with 0.175mol of dodecyl bromide, heated and refluxed for 30 hours, and distilled under reduced pressure after the reaction is finished to obtain a viscous solid which is a main agent crude product.
The main agent crude product is recrystallized by 204g of ethyl acetate and dried for 6 hours at 105 ℃ to obtain the main agent.
(2) Preparation of side agent
1mol of malic acid and 2mol of 10wt% ammonia water are mixed and dissolved uniformly to obtain the side agent.
(3) Preparation of the product
Mixing and dissolving 10g of main agent and 63g of auxiliary agent uniformly to obtain the ammonium salt compound complexing agent L for fracturing 5 。
Example 6 (1) preparation of Main agent
0.05mol of 1,4 cyclohexanedione, 0.102mol of 1-methylpiperazine and 0.18mol of 20wt% formic acid water solution are added into a high-pressure reaction kettle, the temperature is raised to 183 ℃, the reaction is carried out for 20 hours under the heat preservation, after the reaction is finished, the temperature is reduced to below 40 ℃, 48g of chloroform is used for extraction, and the viscous liquid is obtained through reduced pressure distillation.
The viscous liquid is dissolved by 305g of ethanol and transferred into a four-necked flask, 0.19mol of dodecyl bromide is added, the mixture is heated and refluxed for 36 hours, and after the reaction is finished, the viscous solid is obtained by reduced pressure distillation, and is a main agent crude product.
The main agent crude product is recrystallized by 217g of ethyl acetate and dried for 5 hours at 105 ℃ to obtain the main agent.
(2) Preparation of side agent
1mol of citric acid and 3mol of 10wt% ammonia water are mixed and dissolved uniformly to obtain the side agent.
(3) Preparation of the product
Mixing and dissolving 10g of main agent and 60g of auxiliary agent uniformly to obtain the ammonium salt compound complexing agent L for fracturing 6 。
EXAMPLE 7 (1) preparation of the Main agent
0.05mol of 1,4 cyclohexanedione, 0.098mol of 1-methylpiperazine and 0.19mol of 20wt% formic acid water solution are added into a high-pressure reaction kettle, the temperature is raised to 187 ℃, the reaction is kept for 20 hours, after the reaction is completed, the temperature is reduced to below 40 ℃, 50g of chloroform is used for extraction, and the viscous liquid is obtained through reduced pressure distillation.
The viscous liquid is dissolved by 308g of ethanol, transferred into a four-necked flask, added with 0.18mol of dodecyl bromide, heated and refluxed for 48 hours, and distilled under reduced pressure after the reaction is finished to obtain a viscous solid which is a main agent crude product.
And recrystallizing the main agent crude product by using 220g of ethyl acetate, and drying at 105 ℃ for 4 hours to obtain the main agent.
(2) Preparation of side agent
1mol of nitrilotriacetic acid and 3mol of 10wt% ammonia water are mixed and dissolved uniformly to obtain the side agent.
(3) Preparation of the product
Mixing and dissolving 10g of main agent and 55g of auxiliary agent uniformly to obtain the ammonium salt compound complexing agent L for fracturing 7 。
Example 8 (1) preparation of Main agent
0.05mol of 1,4 cyclohexanedione, 0.1mol of 1-methylpiperazine and 0.2mol of 20wt% formic acid aqueous solution are added into a high-pressure reaction kettle, the temperature is raised to 185 ℃, the reaction is kept for 24 hours, after the reaction is completed, the temperature is reduced to below 40 ℃, the chloroform is used for extraction, and the reduced pressure distillation is carried out, so that viscous liquid is obtained.
The viscous liquid is dissolved by 300g of isobutanol, transferred into a four-necked flask, added with 0.18mol of dodecyl bromide, heated and refluxed for 48 hours, and distilled under reduced pressure after the reaction is finished to obtain a viscous solid which is a main agent crude product.
The main agent crude product is recrystallized by 224g of ethyl acetate and dried for 6 hours at 105 ℃ to obtain the main agent.
(2) Preparation of side agent
1mol of ethylenediamine tetraacetic acid and 4mol of 10wt% ammonia water are mixed and dissolved uniformly to obtain the auxiliary agent.
(3) Preparation of the product
Mixing and dissolving 10g of main agent and 50g of auxiliary agent uniformly to obtain the ammonium salt compound complexing agent L for fracturing 8 。
Example 9 evaluation of the anti-swelling Property of the anti-swelling agent
Taking 2g of anti-swelling agent, adding 100g of distilled water, and shaking uniformly to obtain an anti-swelling agent solution.
Weighing 0.50g of sodium bentonite, loading into a 10mL centrifuge tube, adding 10mL of anti-swelling agent solution, shaking thoroughly, standing at room temperature for 2h, loading into a centrifuge, centrifuging at 1500r/min for 15min, and reading the volume V of the swelled sodium bentonite 1 。
Distilled water is used to replace the anti-swelling agent solution, and the volume V of sodium bentonite after swelling 2 。
Volume V of sodium bentonite after swelling by kerosene instead of anti-swelling agent solution 0 。
The calculation method of the anti-swelling rate comprises the following steps:
。
a comparative sample was made with an anti-swelling agent produced by a company.
The results of the anti-swelling agent anti-swelling rate test are shown in Table 1.
As can be seen from table 1:
the ammonium salt compound complexing agent L for fracturing 1 、L 2 、L 3 、L 4 、L 5 、L 6 、L 7 、L 8 Has an anti-swelling ratio of more than 90%, wherein L 8 Up to 96.8%; the comparative sample had an anti-swelling rate of 85.6% which is significantly lower than the present invention.
Example 10 evaluation of Water-washing resistance of anti-swelling agent
The supernatant in the centrifuge tube after centrifugation in example 9 was discarded, 10mL of distilled water was added, and after shaking up sufficiently, the mixture was allowed to stand for 2 hours, and the mixture was put into a centrifuge, subjected to centrifugal separation at a rotational speed of 1500r/min for 15 minutes, and the above operation was repeated twice to read the volume of sodium bentonite after expansion. The calculation was the same as in example 9.
A comparative sample was made with an anti-swelling agent produced by a company.
The results of the water-washing resistance test of the anti-swelling agent are shown in Table 1.
TABLE 1 results of anti-swelling and Water-washing resistance test
As can be seen from table 1:
the ammonium salt compound complexing agent L for fracturing 1 、L 2 、L 3 、L 4 、L 5 、L 6 、L 7 、L 8 The water washing anti-swelling rate of (2) is more than 80 percent, wherein L 8 Up to 86.4%; the water-washing anti-swelling rate of the comparative sample is 70.2%, which is obviously lower than that of the ammonium salt compound complexing agent for fracturing, provided by the invention, and has strong water-washing resistance.
The preferred embodiments of the present invention have been described in detail above, but the present invention is not limited thereto. Within the scope of the technical idea of the invention, a number of simple variants of the technical solution of the invention are possible, including combinations of the individual technical features in any other suitable way, which simple variants and combinations should likewise be regarded as being disclosed by the invention, all falling within the scope of protection of the invention.
Claims (7)
1. The ammonium salt composite complexing agent for fracturing is characterized by comprising a main agent and an auxiliary agent, wherein the auxiliary agent is an aqueous solution of a neutralization product of polycarboxylic acid and ammonia water, and the molecular structural formula of the main agent is as follows:
the polybasic carboxylic acid is one of malic acid, citric acid, nitrilotriacetic acid and ethylenediamine tetraacetic acid;
the mass ratio of the main agent to the auxiliary agent is 1:5-8.
2. The preparation method of the ammonium salt composite complexing agent for fracturing according to claim 1, which is characterized by comprising the following specific steps:
(1) Preparation of the Main agent
Adding 1,4 cyclohexanedione, 1-methylpiperazine and 20wt% formic acid aqueous solution into a high-pressure reaction kettle, heating to 180-190 ℃, carrying out heat preservation reaction, cooling to below 40 ℃ after the reaction is finished, extracting with chloroform, and carrying out reduced pressure distillation to obtain viscous liquid; dissolving the viscous liquid with an organic solvent, transferring to a four-neck flask, adding dodecyl bromide, heating for reflux reaction, and distilling under reduced pressure to obtain a viscous solid which is a main agent crude product after the reaction is finished; recrystallizing the main agent crude product with ethyl acetate, and drying at 105 ℃ for 4-6h to obtain a main agent;
(2) Preparation of side agent
Uniformly mixing and dissolving polybasic carboxylic acid and 10wt% ammonia water according to a certain molar ratio to obtain a side agent;
(3) Preparation of the product
And uniformly mixing and dissolving the main agent and the auxiliary agent to obtain the ammonium salt composite complexing agent for fracturing.
3. The method for preparing an ammonium salt compound complexing agent for fracturing according to claim 2, wherein in the step (1), the 1-methylpiperazine, formic acid and dodecyl bromide are used in an amount of 1.8-2.2 mol parts, 2-4 mol parts and 3.2-4 mol parts, respectively, based on 1mol part of 1,4 cyclohexanedione.
4. The method for preparing an ammonium salt compound complexing agent for fracturing according to claim 3, wherein the dosages of 1-methylpiperazine, formic acid and dodecyl bromide are respectively 1.9-2.1 mol parts, 3-4 mol parts and 3.4-3.8 mol parts based on 1mol part of 1,4 cyclohexanedione.
5. The method for preparing the ammonium salt composite complexing agent for fracturing according to claim 2, wherein in the step (1), the heat preservation reaction time is 12-24 hours.
6. The method for preparing the ammonium salt composite complexing agent for fracturing according to claim 2, wherein in the step (1), the heating reflux reaction time is 24-48h.
7. The method for preparing the ammonium salt composite complexing agent for fracturing according to claim 2, wherein in the step (2), the molar ratio of the polycarboxylic acid to 10wt% of ammonia water is 1:2-4.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102504797A (en) * | 2011-11-22 | 2012-06-20 | 西安石油大学 | Multifunctional clean fracturing fluid |
| CN104194766A (en) * | 2014-09-12 | 2014-12-10 | 西安石油大学 | Clean fracturing fluid and preparation method thereof |
| CN112646559A (en) * | 2019-10-10 | 2021-04-13 | 中国石油化工股份有限公司 | Sand carrying fluid with functions of improving flow resistance of thickened oil and stabilizing clay |
| CN114805440A (en) * | 2022-05-09 | 2022-07-29 | 寿光新海能源技术有限公司 | Clay stabilizer and preparation method thereof |
| CN114853944A (en) * | 2022-05-09 | 2022-08-05 | 寿光新海能源技术有限公司 | Anti-swelling clay stabilizer and preparation method thereof |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102504797A (en) * | 2011-11-22 | 2012-06-20 | 西安石油大学 | Multifunctional clean fracturing fluid |
| CN104194766A (en) * | 2014-09-12 | 2014-12-10 | 西安石油大学 | Clean fracturing fluid and preparation method thereof |
| CN112646559A (en) * | 2019-10-10 | 2021-04-13 | 中国石油化工股份有限公司 | Sand carrying fluid with functions of improving flow resistance of thickened oil and stabilizing clay |
| CN114805440A (en) * | 2022-05-09 | 2022-07-29 | 寿光新海能源技术有限公司 | Clay stabilizer and preparation method thereof |
| CN114853944A (en) * | 2022-05-09 | 2022-08-05 | 寿光新海能源技术有限公司 | Anti-swelling clay stabilizer and preparation method thereof |
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