CN110540618A - Preparation method of temperature-resistant salt-resistant copolymer - Google Patents
Preparation method of temperature-resistant salt-resistant copolymer Download PDFInfo
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Abstract
The invention belongs to the field of chemical synthesis, and relates to a preparation method of a temperature-resistant salt-resistant copolymer. The method comprises the following steps: sequentially adding water, an additive, acrylamide, a functional monomer and a template substance into a reactor, adding an inorganic base to adjust the pH value of a polymerization system, adding an initiator to initiate polymerization reaction, placing the polymerization system in an adiabatic environment, and stopping the reaction when the central temperature of the polymerization system is not increased to obtain a polymer colloid; crushing polymer colloid into colloidal particles, adding a hydrolytic agent for hydrolysis, drying, crushing and screening to obtain the polymer colloid; the template substance is polyacrylic acyloxy ethyl trimethyl ammonium chloride or polymethacrylamidopropyl trimethyl ammonium chloride, and the functional monomer is a sulfonic acid derivative containing terminal alkenyl and a sulfonate derivative thereof; the molar ratio of the template substance to the functional monomer is 0.1-1: 1; the molar ratio of the functional monomer to the acrylamide is 0.05-0.2: 1. The components of the invention are synergistic, and the temperature resistance and salt resistance of the obtained copolymer are obviously improved.
Description
Technical Field
The invention belongs to the field of chemical synthesis, and relates to a preparation method of a temperature-resistant salt-resistant copolymer.
Background
With continuous development of oil fields, the conditions for exploiting oil reservoirs are continuously worsened, oil field exploitation gradually enters second-class and third-class oil reservoir blocks with high temperature and high salt content, currently commonly adopted oil displacement agent polyacrylamide has the defect of poor temperature resistance and salt resistance, the application of the oil reservoirs is difficult to meet, and a large number of researchers modify polyacrylamide to obtain a temperature-resistant salt-resistant copolymer with more excellent performance. The introduction of temperature-resistant and salt-resistant monomers into the polymer structure is one of the common methods for improving the performance of the polymer at present, wherein the functional monomers of the sulfonic acid derivative containing terminal alkenyl and the sulfonate derivative thereof are most widely applied. The sulfonic acid group of the monomer is insensitive to the attack of cations, so that the polymer has good salt resistance, the tolerance of the polymer to calcium and magnesium ions can be improved by introducing the functional monomer, the precipitation is not easy to occur, and the viscosity retention rate is improved, so that the temperature resistance and salt resistance of the polymer can be improved by introducing the functional monomer containing the sulfonic acid group into the polymer, and the more complex oil reservoir conditions can be adapted. The introduction of sodium acrylate structural units into the copolymer can improve the solubility of the polymer, and simultaneously, due to the electrostatic repulsion effect between carboxyl groups, the chain molecular conformation of the polymer is more extended, and the viscosity of the polymer is increased under a certain range of conditions. The molecular structure design of the polymer determines that the polymer has good water solubility, viscosity increasing performance, temperature resistance and salt resistance. However, by adopting the traditional solution polymerization mode, the sequence distribution of the anion functional units is random, and the sequence distribution of the functional monomer units on the macromolecular chains is closely related to the solution performance.
The template polymerization method is an effective method for controlling the composition and sequence distribution of the copolymer, and the principle of the template polymerization method is that a polymer (template) which can interact with a monomer or a growing chain through hydrogen bonds, electrostatic bonding, electron transfer interaction, hydrophobic bonding, Van der Waals force and the like is put into a polymerization system in advance, the monomer is pre-assembled on the template, when the macromolecular chain free radical of the polymerization system meets the template, the pre-assembled monomer on the template is initiated to form a section of monomer block structural unit, and the steps are repeated to form the anionic copolymer with a block structure. Meanwhile, the cationic template is contained in the copolymer system synthesized by the method, the polymer has good solubility under the condition of certain molecular weight and cationic template content, physical crosslinking can be formed between the cationic template and macromolecular chain anionic monomer units through ionic bonds, a supermolecular network structure is constructed, and the solution performance of the polymer is greatly improved. Meanwhile, the complicated purification step of removing the template by a template polymerization method is avoided, the cost is saved, and the method has the value of industrial production.
Chinese patent application (CN102060965A) discloses a preparation method of partially hydrolyzed polyacrylamide with improved temperature and salt resistance. According to the method, a polyacrylamide monomer, a functional monomer and a template substance are mixed according to a mass ratio of 100: 1-10: 0.05-5, the polymerization starting temperature is controlled to be 0-15 ℃, the template substance and the functional monomer in the monomer are more obviously acted under the condition of the temperature, and a polyacrylamide product with a block structure is favorably formed. According to the method, a small amount of functional monomers are polymerized with acrylamide monomers under the action of template substances, and can interact with the template substances in the polymerization process, so that the self-competition rate is improved, and a more complete sequence block structure is obtained; the functional monomer is selected from one of acrylic acid, acrylic acid water-soluble derivative monomer, methacrylic acid water-soluble derivative monomer and the like. The obtained product is prepared into the concentration of 1500ppm in the saline water with the total mineralization of 30000ppm, can be well dissolved by stirring for two hours, and the viscosity of the product at 85 ℃ can reach 16.2 cp.
Disclosure of Invention
The invention mainly aims to provide a preparation method of a copolymer with higher temperature resistance and salt resistance.
In order to achieve the purpose, the invention adopts the following technical scheme:
One of the purposes of the invention is to provide a preparation method of a temperature-resistant and salt-resistant copolymer, which comprises the following steps: sequentially adding water, an additive, acrylamide, a functional monomer and a template substance into a reactor, adding an inorganic base to adjust the pH value of a polymerization system, adding an initiator to initiate polymerization reaction, placing the polymerization system in an adiabatic environment, and stopping the reaction when the central temperature of the polymerization system is not increased to obtain a polymer colloid; crushing polymer colloid into colloidal particles, adding a hydrolytic agent for hydrolysis, drying, crushing and screening to obtain the polymer colloid; the template substance is polyacrylic acyloxy ethyl trimethyl ammonium chloride or polymethacrylamidopropyl trimethyl ammonium chloride, and the functional monomer is a sulfonic acid derivative containing terminal alkenyl and a sulfonate derivative thereof; the molar ratio of the template substance to the functional monomer is (0.1-1) to 1; the molar ratio of the functional monomer to the acrylamide is 0.05-0.2: 1.
In the method, preferably, the molecular weight of the poly (acryloyloxyethyl trimethyl ammonium chloride) is 1000-20000; the molecular weight of the poly (methyl acrylamide propyl trimethyl ammonium chloride) is 1000-30000.
In the above method, preferably, the terminal alkenyl group-containing sulfonic acid derivative and sulfonate derivative thereof include: 2-acrylamido-2-methylpropanesulfonic acid and its sulfonates, vinylsulfonic acid and its sulfonates, and styrenesulfonic acid and its sulfonates.
In the above method, preferably, the additive is composed of EDTA-2Na, urea and sodium formate, the EDTA-2Na content is 0.002 wt% to 0.2 wt% of the acrylamide concentration, the urea content is 0.005 wt% to 10 wt% of the acrylamide concentration, and the sodium formate content is 0.001 wt% to 0.02 wt% of the acrylamide concentration.
In the above method, preferably, the initiator is a redox system composed of an oxidizing agent and a reducing agent, the oxidizing agent is a persulfate, and preferably, the persulfate is selected from one of potassium persulfate and ammonium persulfate; the reducing agent is sulfite, preferably, the sulfite is selected from one of sodium bisulfite, sodium sulfite and sodium metabisulfite; the mass ratio of the oxidant to the reducer is 1:1, and the addition amount of the oxidant or the reducer is 0.01 wt% -0.2 wt% of the concentration of acrylamide. In the scheme of the invention, the initiator is completely composed of the inorganic salt oxidant and the inorganic salt reducing agent, and the initiator is not only cheap but also high in initiating efficiency.
In the method, preferably, the concentration of the acrylamide is 10 wt% to 30 wt%, the pH value of the polymerization system is 5 to 7, and the initiation temperature is-5 ℃ to 30 ℃.
In the method, preferably, the hydrolyzing agent is added according to the hydrolysis degree, the hydrolysis degree is 5-25%, and the hydrolyzing agent is sodium hydroxide.
In the method, preferably, the hydrolysis temperature is 80-110 ℃, the hydrolysis time is 1.0-4.0 h, the drying temperature is 90-110 ℃, and the drying time is 40 min-3 h.
The second object of the present invention is to provide a temperature-resistant and salt-resistant copolymer prepared by the above preparation method.
Preferably, the copolymer has a viscosity average molecular weight of 1000 to 2500 ten thousand.
The monomer contains sulfonic acid groups and can show insensitivity to attack of cations, so that the polymer has good salt resistance, but only randomly distributed polymers can be obtained by a common polymerization method at present, and the influence of the block distribution of sulfonic functional monomers on the performance of the copolymer is rarely reported. According to the invention, poly (acryloyloxyethyl trimethyl ammonium chloride) or poly (methacrylamide) propyl trimethyl ammonium chloride is used as a template substance, a sulfonic acid derivative containing terminal alkenyl and a sulfonate derivative thereof are used as functional monomers to perform a polymerization reaction with acrylamide, and then the post-hydrolysis is performed, so that the obtained copolymer has good temperature and salt resistance, and further research shows that in the reaction process, the temperature and salt resistance of the obtained copolymer can be obviously influenced by the proportion of the template substance to the sulfonic acid derivative containing terminal alkenyl and the sulfonate derivative thereof, and the temperature and salt resistance of the obtained copolymer is optimal when the molar ratio of the template substance to the functional monomers is 0.1-1: 1. In addition, all the components of the invention are synergistic, and the temperature resistance and salt resistance of the prepared copolymer are obviously improved.
Detailed Description
It is to be understood that the following detailed description is exemplary and is intended to provide further explanation of the invention as claimed. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
It is noted that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of exemplary embodiments according to the invention. As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, and it should be understood that when the terms "comprises" and/or "comprising" are used in this specification, they specify the presence of the stated features, steps, operations, and/or combinations thereof, unless the context clearly indicates otherwise.
In order to make the technical solutions of the present invention more clearly understood by those skilled in the art, the technical solutions of the present invention will be described in detail below with reference to specific embodiments.
Example 1
Water, EDTA-2Na, urea, sodium formate, acrylamide, a functional monomer, namely 2-acrylamido-2-methylpropanesulfonic acid and a template, namely polymethacrylamidopropyl trimethyl ammonium chloride (the molecular weight of the template is 15000) are sequentially added into a reaction vessel, the concentration of acrylamide monomers in a polymerization system is controlled to be 25 wt%, the concentration of EDTA-2Na, the concentration of urea and the concentration of sodium formate are respectively 0.05 wt%, 2 wt% and 0.002 wt% of the concentration of acrylamide, the molar ratio of the content of 2-acrylamido-2-methylpropanesulfonic acid to the content of acrylamide monomers is 0.08:1, the molar ratio of a cationic template monomer unit to the 2-acrylamido-2-methylpropanesulfonic acid monomer is 0.2:1, inorganic base sodium hydroxide is added to adjust the pH value of the system to be 7.5, a persulfuric acid composite initiator consisting of potassium and sodium bisulfite is added at 5, the mass ratio of potassium persulfate to sodium bisulfite is 1:1, the content of potassium persulfate is 0.03 wt% of the total concentration of the monomers, the polymerization system is placed in an adiabatic environment, and the reaction is stopped when the central temperature of the polymerization system is raised to the maximum.
Crushing polymer colloid into 2-3 mm colloidal particles, adding a hydrolytic agent sodium hydroxide according to the hydrolysis degree of 15%, carrying out hydrolysis reaction for 2h at 95 ℃, hydrolyzing part of acrylamide units to form a sodium acrylate unit structure, drying for 1h at 95 ℃, crushing and screening to obtain the temperature-resistant salt-resistant copolymer containing the template. The temperature-resistant salt-resistant copolymer obtained in example 1 was tested in GB/T12005.10-92 using an Ubbelohde viscometer (0.55mm diameter tube) and had a viscosity average molecular weight of 1895 ten thousand.
The dry polymer powder obtained in example 1 was dissolved in saline water having a total mineralization of 5.5X 104mg/L and a total calcium/magnesium ion concentration of 5000mg/L at 30 ℃ to prepare a polymer solution having a concentration of 5000mg/L, a polymer dissolution time of 2.0 hours, a target polymer solution concentration of 2000mg/L, a viscosity of 88mPa at 25 ℃ and 7.34s-1, a viscosity of 54mPa s at 88 ℃ and 7.34s-1, a viscosity of 45mPa s at 95 ℃ and 7.34s-1, and a viscosity of 41mPa s at 100 ℃ and 7.34 s-1.
Example 2
According to the polymerization method and steps in the embodiment 1, the molar ratio of the polymethacrylamidopropyl trimethyl ammonium chloride to the 2-acrylamido-2-methylpropanesulfonic acid monomer is changed to 0.1:1, so as to obtain the temperature-resistant and salt-resistant copolymer containing the template, and other steps are the same as those in the embodiment 1. The temperature-resistant salt-resistant copolymer obtained in example 2 was tested in GB/T12005.10-92 using an Ubbelohde viscometer (0.55mm diameter tube) and had a viscosity average molecular weight of 1942 ten thousand.
The dry polymer powder obtained in example 2 was dissolved in saline water having a total mineralization of 5.5X 104mg/L and a total concentration of calcium and magnesium ions of 5000mg/L at 30 ℃ to prepare a polymer solution having a concentration of 5000mg/L, a polymer dissolution time of 2.0 hours, a target polymer solution concentration of 2000mg/L, a viscosity of 70 mPas at 25 ℃ and 7.34s-1, a viscosity of 41 mPas at 88 ℃ and 7.34s-1, a viscosity of 32 mPas at 95 ℃ and 7.34s-1, and a viscosity of 19 mPas at 100 ℃ and 7.34 s-1.
Example 3
According to the polymerization method and steps in the embodiment 1, the molar ratio of the polymethacrylamidopropyl trimethyl ammonium chloride to the 2-acrylamido-2-methylpropanesulfonic acid monomer is changed to 0.4:1, so as to obtain the temperature-resistant and salt-resistant copolymer containing the template, and other steps are the same as those in the embodiment 1. The temperature-resistant salt-resistant copolymer obtained in example 3 was tested in GB/T12005.10-92 using an Ubbelohde viscometer (0.55mm pipe diameter) to give a viscosity average molecular weight of 1805 ten thousand.
The dry polymer powder obtained in example 3 was dissolved in saline water having a total mineralization of 5.5X 104mg/L and a total concentration of calcium and magnesium ions of 5000mg/L at 30 ℃ to prepare a polymer solution having a concentration of 5000mg/L, a polymer dissolution time of 3.0 hours, a target polymer solution concentration of 2000mg/L, a viscosity of 115 mPas at 25 ℃ and 7.34s-1, a viscosity of 68 mPas at 88 ℃ and 7.34s-1, a viscosity of 60 mPas at 95 ℃ and 7.34s-1, and a viscosity of 57 mPas at 100 ℃ and 7.34 s-1.
Example 4
According to the polymerization method and steps in the embodiment 1, the molar ratio of the polymethacrylamidopropyl trimethyl ammonium chloride to the 2-acrylamido-2-methylpropanesulfonic acid monomer is changed to 0.8:1, so as to obtain the temperature-resistant and salt-resistant copolymer containing the template, and other steps are the same as those in the embodiment 1. The temperature-resistant salt-resistant copolymer obtained in example 4 was tested in GB/T12005.10-92 using an Ubbelohde viscometer (0.55mm diameter tube) to give a viscosity average molecular weight of 1725 ten thousand.
The dry polymer powder obtained in example 4 was dissolved in saline water having a total mineralization of 5.5X 104mg/L and a total calcium/magnesium ion concentration of 5000mg/L at 30 ℃ to prepare a polymer solution having a concentration of 5000mg/L, a polymer dissolution time of 4.0 hours, a target polymer solution concentration of 2000mg/L, a viscosity of 130 mPas at 25 ℃ and 7.34s-1, a viscosity of 75 mPas at 88 ℃ and 7.34s-1, a viscosity of 72 mPas at 95 ℃ and 7.34s-1, and a viscosity of 69 mPas at 100 ℃ and 7.34 s-1.
example 5
According to the polymerization method and steps in the embodiment 1, the molar ratio of the poly (methacrylamidopropyltrimethylammonium chloride) to the 2-acrylamido-2-methylpropanesulfonic acid monomer is changed to 1:1, so as to obtain the temperature-resistant and salt-resistant copolymer containing the template, and other steps are the same as those in the embodiment 1. The temperature-resistant salt-resistant copolymer obtained in example 5 was tested in GB/T12005.10-92 using an Ubbelohde viscometer (0.55mm caliber), and had a viscosity average molecular weight of 1701 ten thousand.
The dry polymer powder obtained in example 5 was dissolved in saline water having a total mineralization of 5.5X 104mg/L and a total concentration of calcium and magnesium ions of 5000mg/L at 30 ℃ to prepare a polymer solution having a concentration of 5000mg/L, a polymer dissolution time of 5.0 hours, a target polymer solution concentration of 2000mg/L, a viscosity of 100 mPas at 25 ℃ and 7.34s-1, a viscosity of 58 mPas at 88 ℃ and 7.34s-1, a viscosity of 46 mPas at 95 ℃ and 7.34s-1, and a viscosity of 39 mPas at 100 ℃ and 7.34 s-1.
Example 6
According to the polymerization method and steps in the embodiment 1, the mole ratio of the polymethacrylamidopropyl trimethyl ammonium chloride to the 2-acrylamide-2-methyl propanesulfonic acid monomer is changed to 0.4:1, the molecular weight of the cationic template is changed to 1000, and the temperature-resistant and salt-resistant copolymer containing the template is obtained, and other steps are the same as the embodiment 1. The temperature-resistant salt-resistant copolymer obtained in example 6 was tested in GB/T12005.10-92 using an Ubbelohde viscometer (0.55mm diameter tube) and had a viscosity average molecular weight of 1982 ten thousand.
The dry polymer powder obtained in example 6 was dissolved in saline water having a total mineralization of 5.5X 104mg/L and a total concentration of calcium and magnesium ions of 5000mg/L at 30 ℃ to prepare a polymer solution having a concentration of 5000mg/L, a polymer dissolution time of 3.0 hours, a target polymer solution concentration of 2000mg/L, a viscosity of 73 mPas at 25 ℃ and 7.34s-1, a viscosity of 43 mPas at 88 ℃ and 7.34s-1, a viscosity of 35 mPas at 95 ℃ and 7.34s-1, and a viscosity of 28 mPas at 100 ℃ and 7.34 s-1.
Example 7
According to the polymerization method and steps in the example 1, the mole ratio of the cationic template monomer unit to the 2-acrylamide-2-methylpropanesulfonic acid monomer is changed to 0.1:1, the cationic template molecular weight is changed to 30000, and the temperature-resistant and salt-resistant copolymer containing the template is obtained, and other steps are the same as those in the example 1. The temperature-resistant salt-resistant copolymer obtained in example 7 was tested in GB/T12005.10-92 using an Ubbelohde viscometer (0.55mm diameter tube) and had a viscosity average molecular weight of 1954 ten thousand.
The dry polymer powder obtained in example 7 was dissolved in saline water having a total mineralization of 5.5X 104mg/L and a total concentration of calcium and magnesium ions of 5000mg/L at 30 ℃ to prepare a polymer solution having a concentration of 5000mg/L, a polymer dissolution time of 4.0 hours, a target polymer solution concentration of 2000mg/L, a viscosity of 105 mPas at 25 ℃ and 7.34s-1, a viscosity of 65 mPas at 88 ℃ and 7.34s-1, a viscosity of 62 mPas at 95 ℃ and 7.34s-1, and a viscosity of 58 mPas at 100 ℃ and 7.34 s-1.
Example 8
According to the polymerization method and steps in example 1, the mole ratio of 2-acrylamido-2-methylpropanesulfonic acid to acrylamide monomer was changed to 0.15:1, and the content of potassium persulfate was changed to 0.012 wt%, to obtain the template-containing temperature-resistant salt-resistant copolymer, and the other steps were the same as in example 1. The temperature-resistant salt-resistant copolymer obtained in example 8 was tested in GB/T12005.10-92 using an Ubbelohde viscometer (0.55mm diameter tube) to give a viscosity average molecular weight of 2305 ten thousand.
The dry polymer powder obtained in example 8 was dissolved in saline water at 30 ℃ and having a total mineralization of 5.5X 104mg/L and a total concentration of calcium and magnesium ions of 5000mg/L to prepare a polymer solution having a concentration of 5000mg/L, a polymer dissolution time of 2.5 hours, a target polymer solution concentration of 2000mg/L, a viscosity of 130 mPas at 25 ℃ and 7.34s-1, a viscosity of 78 mPas at 88 ℃ and 7.34s-1, a viscosity of 65 mPas at 95 ℃ and 7.34s-1, and a viscosity of 61 mPas at 100 ℃ and 7.34 s-1.
Example 9
According to the polymerization method and procedure in example 1, the molar ratio of 2-acrylamido-2-methylpropanesulfonic acid to acrylamide was changed to 0.2:1, and the content of potassium persulfate was changed to 0.012 wt%, to obtain a temperature-resistant and salt-resistant copolymer containing a template, and the other procedures were the same as in example 1. The temperature-resistant salt-resistant copolymer obtained in example 9 was tested in GB/T12005.10-92 using an Ubbelohde viscometer (0.55mm diameter tube) to give a viscosity average molecular weight of 1925 ten thousand.
The dry polymer powder obtained in example 9 was dissolved in saline water at 30 ℃ and having a total mineralization of 5.5X 104mg/L and a total concentration of calcium and magnesium ions of 5000mg/L to prepare a polymer solution having a concentration of 5000mg/L, a polymer dissolution time of 2.5 hours, a target polymer solution concentration of 2000mg/L, a viscosity of 120 mPas at 25 ℃ and 7.34s-1, a viscosity of 73 mPas at 88 ℃ and 7.34s-1, a viscosity of 69 mPas at 95 ℃ and 7.34s-1, and a viscosity of 65 mPas at 100 ℃ and 7.34 s-1. .
Example 10
According to the polymerization method and procedure in example 1, the temperature-resistant salt-resistant copolymer containing the template was obtained by changing the acrylamide concentration to 10 wt%, the EDTA-2Na content to 0.1 wt%, the sodium formate content to 0.001 wt%, and the potassium persulfate content to 0.2 wt%, and the other procedures were the same as in example 1. The temperature-resistant salt-resistant copolymer obtained in example 10 was tested in GB/T12005.10-92 using an Ubbelohde viscometer (0.55mm diameter tube) to give a viscosity average molecular weight of 1030 ten thousand.
The dry polymer powder obtained in example 10 was dissolved in saline water at 30 ℃ and having a total mineralization of 5.5X 104mg/L and a total concentration of calcium and magnesium ions of 5000mg/L to prepare a polymer solution having a concentration of 5000mg/L, a polymer dissolution time of 2.0 hours, a target polymer solution concentration of 2000mg/L, a viscosity of 59 mPas at 25 ℃ and 7.34s-1, a viscosity of 35 mPas at 88 ℃ and 7.34s-1, a viscosity of 20 mPas at 95 ℃ and 7.34s-1, and a viscosity of 15 mPas at 100 ℃ and 7.34 s-1.
Example 11
According to the polymerization method and steps in the example 1, the temperature-resistant salt-resistant copolymer containing the template is obtained by changing the acrylamide concentration to 20%, the EDTA-2Na content to 0.002 wt%, the urea content to 0.005 wt%, the oxidant potassium persulfate to ammonium persulfate, and the ammonium persulfate content to 0.025 wt%, and other steps are the same as those in the example 1. The temperature-resistant salt-resistant copolymer obtained in example 11 was tested in GB/T12005.10-92 using an Ubbelohde viscometer (0.55mm diameter tube) and had a viscosity average molecular weight of 1900 ten thousand.
The dry polymer powder obtained in example 11 was dissolved in saline water at 30 ℃ and having a total mineralization of 5.5X 104mg/L and a total concentration of calcium and magnesium ions of 5000mg/L to prepare a polymer solution having a concentration of 5000mg/L, a polymer dissolution time of 3.0 hours, a target polymer solution concentration of 2000mg/L, a viscosity of 100 mPas at 25 ℃ and 7.34s-1, a viscosity of 58 mPas at 88 ℃ and 7.34s-1, a viscosity of 46 mPas at 95 ℃ and 7.34s-1, and a viscosity of 40 mPas at 100 ℃ and 7.34 s-1.
Example 12
According to the polymerization method and steps in example 1, the acrylamide concentration was changed to 30%, the EDTA-2Na content was changed to 0.02 wt%, the urea content was changed to 10 wt%, the pH value was changed to 8.5, the sodium formate content was changed to 0.02 wt%, and the potassium persulfate content was changed to 0.04 wt%, to obtain the template-containing temperature-resistant salt-resistant copolymer, and the other steps were the same as in example 1. The temperature-resistant salt-resistant copolymer obtained in example 12 was tested in GB/T12005.10-92 using an Ubbelohde viscometer (0.55mm diameter tube) to give a viscosity average molecular weight of 1735 ten thousand.
The dry polymer powder obtained in example 12 was dissolved in saline water at 30 ℃ and having a total mineralization of 5.5X 104mg/L and a total concentration of calcium and magnesium ions of 5000mg/L to prepare a polymer solution having a concentration of 5000mg/L, a polymer dissolution time of 3.5 hours, a target polymer solution concentration of 2000mg/L, a viscosity of 85 mPas at 25 ℃ and 7.34s-1, a viscosity of 49 mPas at 88 ℃ and 7.34s-1, a viscosity of 39 mPas at 95 ℃ and 7.34s-1, and a viscosity of 32 mPas at 100 ℃ and 7.34 s-1.
Example 13
According to the polymerization method and steps in the example 1, the temperature resistance and salt tolerance copolymer containing the template is obtained by changing the initiation temperature to-5 ℃ and the pH value of the polymerization system to 5, and other steps are the same as those in the example 1. The temperature-resistant salt-resistant copolymer obtained in example 13 was tested in GB/T12005.10-92 using an Ubbelohde viscometer (0.55mm diameter tube) and had a viscosity average molecular weight of 1825 ten thousand.
The dry polymer powder obtained in example 13 was dissolved in saline water at 30 ℃ and having a total mineralization of 5.5X 104mg/L and a total concentration of calcium and magnesium ions of 5000mg/L to prepare a polymer solution having a concentration of 5000mg/L, a polymer dissolution time of 3.0 hours, a target polymer solution concentration of 2000mg/L, a viscosity of 96 mPas at 25 ℃ and 7.34s-1, a viscosity of 58 mPas at 88 ℃ and 7.34s-1, a viscosity of 42 mPas at 95 ℃ and 7.34s-1, and a viscosity of 37 mPas at 100 ℃ and 7.34 s-1.
Example 14
The polymerization process and procedure of example 1 were followed, except that the initiation temperature was changed to 16 deg.C, the reducing agent was changed to sodium sulfite, and the potassium persulfate content was changed to 0.02 wt%, to obtain a temperature-resistant salt-resistant copolymer containing a template, and the other procedures were the same as those of example 1. The temperature-resistant salt-resistant copolymer obtained in example 14 was tested in GB/T12005.10-92 using an Ubbelohde viscometer (0.55mm diameter tube) to give a viscosity average molecular weight of 1524 ten thousand.
The dry polymer powder obtained in example 14 was dissolved in saline water at 30 ℃ and having a total mineralization of 5.5X 104mg/L and a total concentration of calcium and magnesium ions of 5000mg/L to prepare a polymer solution having a concentration of 5000mg/L, a polymer dissolution time of 2.5 hours, a target polymer solution concentration of 2000mg/L, a viscosity of 75 mPas at 25 ℃ and 7.34s-1, a viscosity of 45 mPas at 88 ℃ and 7.34s-1, a viscosity of 35 mPas at 95 ℃ and 7.34s-1, and a viscosity of 29 mPas at 100 ℃ and 7.34 s-1.
Example 15
According to the polymerization method and steps in example 1, the initiation temperature was changed to 30 ℃, the pH of the polymerization system was changed to 10, the reducing agent was changed to sodium metabisulfite, and the potassium persulfate content was changed to 0.05 wt%, to obtain the template-containing temperature-resistant salt-resistant copolymer, and the other steps were the same as in example 1. The temperature-resistant salt-resistant copolymer obtained in example 15 was tested in GB/T12005.10-92 using an Ubbelohde viscometer (0.55mm diameter tube) and had a viscosity average molecular weight of 1325 ten thousand.
The dry polymer powder obtained in example 15 was dissolved in saline water at 30 ℃ and having a total mineralization of 5.5X 104mg/L and a total concentration of calcium and magnesium ions of 5000mg/L to prepare a polymer solution having a concentration of 5000mg/L, a polymer dissolution time of 2.0 hours, a target polymer solution concentration of 2000mg/L, a viscosity of 62 mPas at 25 ℃ and 7.34s-1, a viscosity of 39 mPas at 88 ℃ and 7.34s-1, a viscosity of 28 mPas at 95 ℃ and 7.34s-1, and a viscosity of 19 mPas at 100 ℃ and 7.34 s-1.
Example 16
The temperature and salt resistant copolymer containing the template was obtained by changing the hydrolysis temperature to 80 ℃ and the hydrolysis time to 4 hours according to the polymerization method and procedure of example 1, and the other procedures were the same as those of example 1. The temperature-resistant salt-resistant copolymer obtained in example 16 was tested in GB/T12005.10-92 using an Ubbelohde viscometer (0.55mm diameter tube) and had a viscosity average molecular weight of 1792 ten thousand.
The dry polymer powder obtained in example 16 was dissolved in saline water at 30 ℃ and having a total mineralization of 5.5X 104mg/L and a total concentration of calcium and magnesium ions of 5000mg/L to prepare a polymer solution having a concentration of 5000mg/L, a polymer dissolution time of 4.5 hours, a target polymer solution concentration of 2000mg/L, a viscosity of 81 mPas at 25 ℃ and 7.34s-1, a viscosity of 48 mPas at 88 ℃ and 7.34s-1, a viscosity of 40 mPas at 95 ℃ and 7.34s-1, and a viscosity of 32 mPas at 100 ℃ and 7.34 s-1.
Example 17
The temperature and salt resistant copolymer containing the template was obtained by changing the hydrolysis temperature to 110 ℃ and the hydrolysis time to 1 hour according to the polymerization method and procedure of example 1, and the other procedures were the same as those of example 1. The temperature-resistant salt-resistant copolymer obtained in example 17 was tested in GB/T12005.10-92 using an Ubbelohde viscometer (0.55mm caliber), and its viscosity-average molecular weight was 1858 ten thousand.
The dry polymer powder obtained in example 17 was dissolved in saline water at 30 ℃ and having a total mineralization of 5.5X 104mg/L and a total concentration of calcium and magnesium ions of 5000mg/L to prepare a polymer solution having a concentration of 5000mg/L, a polymer dissolution time of 3.5 hours, a target polymer solution concentration of 2000mg/L, a viscosity of 95 mPas at 25 ℃ and 7.34s-1, a viscosity of 55 mPas at 88 ℃ and 7.34s-1, a viscosity of 45 mPas at 95 ℃ and 7.34s-1, and a viscosity of 35 mPas at 100 ℃ and 7.34s-1
Example 18
The polymerization process and procedure of example 1 were followed, except that the drying temperature was changed to 90 ℃ and the drying time was changed to 2.5 hours, to obtain a temperature-resistant salt-resistant copolymer containing a template, which was the same as in example 1. The temperature-resistant salt-resistant copolymer obtained in example 18 was tested in GB/T12005.10-92 using an Ubbelohde viscometer (0.55mm diameter tube) to give a viscosity average molecular weight of 1888 ten thousand.
The dry polymer powder obtained in example 18 was dissolved in saline water at 30 ℃ and having a total mineralization of 5.5X 104mg/L and a total concentration of calcium and magnesium ions of 5000mg/L to prepare a polymer solution having a concentration of 5000mg/L, a polymer dissolution time of 3.5 hours, a target polymer solution concentration of 2000mg/L, a viscosity of 97 mPas at 25 ℃ and 7.34s-1, a viscosity of 56 mPas at 88 ℃ and 7.34s-1, a viscosity of 48 mPas at 95 ℃ and 7.34s-1, and a viscosity of 42 mPas at 100 ℃ and 7.34 s-1.
Example 19
The polymerization process and procedure of example 1 were followed, except that the drying temperature was changed to 110 ℃ and the drying time was changed to 40min, to obtain a temperature-resistant salt-resistant copolymer containing a template, which was the same as in example 1. The temperature-resistant salt-resistant copolymer obtained in example 19 was tested in GB/T12005.10-92 using an Ubbelohde viscometer (0.55mm diameter tube) to give a viscosity average molecular weight of 1758 ten thousand.
The dry polymer powder obtained in example 19 was dissolved in saline water at 30 ℃ and having a total mineralization of 5.5X 104mg/L and a total concentration of calcium and magnesium ions of 5000mg/L to prepare a polymer solution having a concentration of 5000mg/L, a polymer dissolution time of 3.0 hours, a target polymer solution concentration of 2000mg/L, a viscosity of 87 mPas at 25 ℃ and 7.34s-1, a viscosity of 49 mPas at 88 ℃ and 7.34s-1, a viscosity of 41 mPas at 95 ℃ and 7.34s-1, and a viscosity of 34 mPas at 100 ℃ and 7.34s-1
Example 20
The temperature-resistant salt-resistant copolymer containing the template was obtained by changing the degree of hydrolysis to 5% according to the polymerization method and procedure in example 1, and the other procedures were the same as in example 1. The temperature-resistant salt-resistant copolymer obtained in example 20 was tested in GB/T12005.10-92 using an Ubbelohde viscometer (0.55mm diameter tube) and had a viscosity average molecular weight of 1820 ten thousand.
The dry polymer powder obtained in example 20 was dissolved in saline water at 30 ℃ and having a total mineralization of 5.5X 104mg/L and a total concentration of calcium and magnesium ions of 5000mg/L to prepare a polymer solution having a concentration of 5000mg/L, a polymer dissolution time of 4.0 hours, a target polymer solution concentration of 2000mg/L, a viscosity of 75 mPas at 25 ℃ and 7.34s-1, a viscosity of 44 mPas at 88 ℃ and 7.34s-1, a viscosity of 36 mPas at 95 ℃ and 7.34s-1, and a viscosity of 30 mPas at 100 ℃ and 7.34 s-1.
Example 21
The temperature-resistant salt-resistant copolymer containing the template was obtained by changing the degree of hydrolysis to 30% according to the polymerization method and procedure in example 1, and the other procedures were the same as in example 1. The temperature-resistant salt-resistant copolymer obtained in example 21 was tested in GB/T12005.10-92 using an Ubbelohde viscometer (0.55mm diameter tube) to give a viscosity average molecular weight of 1832 ten thousand.
The dry polymer powder obtained in example 21 was dissolved in saline water at 30 ℃ and having a total mineralization of 5.5X 104mg/L and a total concentration of calcium and magnesium ions of 5000mg/L to prepare a polymer solution having a concentration of 5000mg/L, a polymer dissolution time of 2.5 hours, a target polymer solution concentration of 2000mg/L, a viscosity of 90 mPas at 25 ℃ and 7.34s-1, a viscosity of 50 mPas at 88 ℃ and 7.34s-1, a viscosity of 38 mPas at 95 ℃ and 7.34s-1, and a viscosity of 30 mPas at 100 ℃ and 7.34 s-1.
Example 22
According to the polymerization method and steps in the embodiment 1, the anionic functional monomer 2-acrylamide-2-methyl propanesulfonic acid is changed into vinyl sulfonic acid to obtain the temperature-resistant and salt-resistant copolymer containing the template, and other steps are the same as the embodiment 1. The temperature-resistant salt-resistant copolymer obtained in example 22 was tested in GB/T12005.10-92 using an Ubbelohde viscometer (0.55mm diameter tube) to give a viscosity average molecular weight of 1905 ten thousand.
The dry polymer powder obtained in example 22 was dissolved in saline water at 30 ℃ and having a total mineralization of 5.5X 104mg/L and a total concentration of calcium and magnesium ions of 5000mg/L to prepare a polymer solution having a concentration of 5000mg/L, a polymer dissolution time of 3.0 hours, a target polymer solution concentration of 2000mg/L, a viscosity of 91 mPas at 25 ℃ and 7.34s-1, a viscosity of 52 mPas at 88 ℃ and 7.34s-1, a viscosity of 41 mPas at 95 ℃ and 7.34s-1, and a viscosity of 38 mPas at 100 ℃ and 7.34 s-1.
Example 23
According to the polymerization method and steps in the embodiment 1, the anionic functional monomer 2-acrylamide-2-methyl propanesulfonic acid is changed into styrene sulfonic acid to obtain the temperature-resistant and salt-resistant copolymer containing the template, and other steps are the same as the embodiment 1. The temperature-resistant salt-resistant copolymer obtained in example 23 was tested in GB/T12005.10-92 using an Ubbelohde viscometer (0.55mm diameter tube) and had a viscosity average molecular weight of 1800 ten thousand.
The dry polymer powder obtained in example 23 was dissolved in saline water having a total mineralization of 5.5X 104mg/L and a total calcium/magnesium ion concentration of 5000mg/L at 30 ℃ to prepare a polymer solution having a concentration of 5000mg/L, a polymer dissolution time of 3.3 hours, a target polymer solution concentration of 2000mg/L, a viscosity of 92 mPas at 25 ℃ and 7.34s-1, a viscosity of 59 mPas at 88 ℃ and 7.34s-1, a viscosity of 49 mPas at 95 ℃ and 7.34s-1, and a viscosity of 45 mPas at 100 ℃ and 7.34 s-1.
Example 24
According to the polymerization method and steps in example 1, polymethacrylamidopropyltrimethylammonium chloride was replaced by polyacryloyloxyethyltrimethylammonium chloride, the molar ratio of the polymethacrylamidopropyltrimethylammonium chloride to the 2-acrylamido-2-methylpropanesulfonic acid monomer was 0.2:1, the molar ratio of the 2-acrylamido-2-methylpropanesulfonic acid to the acrylamide monomer was changed to 0.15:1, and the amount of potassium persulfate was changed to 0.015 wt%, so as to obtain a template-containing temperature-resistant and salt-resistant copolymer, and the other steps were the same as in example 1. The temperature-resistant salt-resistant copolymer obtained in example 24 was tested in GB/T12005.10-92 using an Ubbelohde viscometer (0.55mm diameter tube) to give a viscosity average molecular weight of 2215 ten thousand.
The dry polymer powder obtained in example 24 was dissolved in saline water at 30 ℃ and having a total mineralization of 5.5X 104mg/L and a total calcium/magnesium ion concentration of 5500mg/L to prepare a 5000mg/L polymer solution having a polymer dissolution time of 2.5 hours, a target polymer solution concentration of 2000mg/L, a viscosity of 125 mPas at 25 ℃ and 7.34s-1, a viscosity of 75 mPas at 88 ℃ and 7.34s-1, a viscosity of 68 mPas at 95 ℃ and 7.34s-1, and a viscosity of 59 mPas at 100 ℃ and 7.34 s-1.
Comparative example 1
According to the polymerization method and steps in the embodiment 1, the molar ratio of the polymethacrylamidopropyl trimethyl ammonium chloride to the 2-acrylamido-2-methylpropanesulfonic acid monomer is changed to 0.01:1, so as to obtain the temperature-resistant and salt-resistant copolymer containing the template, and other steps are the same as those in the embodiment 1. The temperature-resistant and salt-resistant copolymer obtained in comparative example 1 was tested in GB/T12005.10-92 using a Ubbelohde viscometer (0.55mm diameter tube) to obtain a viscosity average molecular weight of 2000 ten thousand.
The dry polymer powder obtained in comparative example 1 was dissolved in saline water having a total mineralization of 5.5X 104mg/L and a total calcium/magnesium ion concentration of 5000mg/L at 30 ℃ to prepare a polymer solution having a concentration of 5000mg/L, a polymer dissolution time of 1.5 hours, a target polymer solution concentration of 2000mg/L, a viscosity of 35 mPas at 25 ℃ and 7.34s-1, a viscosity of 15 mPas at 88 ℃ and 7.34s-1, a viscosity of 10 mPas at 95 ℃ and 7.34s-1, and a viscosity of 5 mPas at 100 ℃ and 7.34 s-1.
Comparative example 2
According to the polymerization method and steps in the example 1, the mole ratio of the polymethacrylamidopropyl trimethyl ammonium chloride to the 2-acrylamido-2-methylpropanesulfonic acid monomer is changed to 0.4:1, the mole ratio of the 2-acrylamido-2-methylpropanesulfonic acid to the total mole number of the monomers is changed to 0.001:1, the potassium persulfate content is changed to 0.012 wt%, and the temperature-resistant and salt-resistant copolymer containing the template is obtained, and other steps are the same as the example 1. The temperature-resistant and salt-resistant copolymer obtained in comparative example 2 of GB/T12005.10-92 was tested using a Ubbelohde viscometer (0.55mm diameter) to obtain a viscosity average molecular weight of 2415 ten thousand.
The dry polymer powder obtained in comparative example 2 was dissolved in saline water having a total mineralization of 5.5X 104mg/L and a total calcium/magnesium ion concentration of 5000mg/L at 30 ℃ to prepare a polymer solution having a concentration of 5000mg/L, a polymer dissolution time of 3.5 hours, a target polymer solution concentration of 2000mg/L, a viscosity of 61 mPas at 25 ℃ and 7.34s-1, a viscosity of 30 mPas at 88 ℃ and 7.34s-1, a viscosity of 22 mPas at 95 ℃ and 7.34s-1, and a viscosity of 15 mPas at 100 ℃ and 7.34 s-1.
Comparative example 3
The polymerization process and procedure of example 1 were followed to change the degree of hydrolysis to 0.05% to obtain a temperature-resistant salt-resistant copolymer containing a template, and the other procedures were the same as in example 1. The temperature-resistant and salt-resistant copolymer obtained in comparative example 3 was tested in GB/T12005.10-92 using a Ubbelohde viscometer (0.55mm diameter tube) to obtain a viscosity average molecular weight of 1800 ten thousand.
The dry polymer powder obtained in comparative example 3 was dissolved in saline water having a total mineralization of 5.5X 104mg/L and a total calcium/magnesium ion concentration of 5000mg/L at 30 ℃ to prepare a polymer solution having a concentration of 5000mg/L, a polymer dissolution time of 5.5 hours, a target polymer solution concentration of 2000mg/L, a viscosity of 42 mPas at 25 ℃ and 7.34s-1, a viscosity of 25 mPas at 88 ℃ and 7.34s-1, a viscosity of 20 mPas at 95 ℃ and 7.34s-1, and a viscosity of 14 mPas at 100 ℃ and 7.34 s-1.
Comparative example 4
According to the polymerization method and steps in the embodiment 1, the anionic functional monomer 2-acrylamide-2-methyl propanesulfonic acid is changed into N-ethyl acrylamide to obtain the temperature-resistant and salt-resistant copolymer containing the template, and other steps are the same as the embodiment 1. The temperature-resistant and salt-resistant copolymer obtained in comparative example 4 was tested in GB/T12005.10-92 using a Ubbelohde viscometer (0.55mm diameter tube) to obtain a viscosity average molecular weight of 2001 ten thousand.
The dry polymer powder obtained in comparative example 4 was dissolved in saline water having a total mineralization of 5.5X 104mg/L and a total calcium/magnesium ion concentration of 5000mg/L at 30 ℃ to prepare a polymer solution having a concentration of 5000mg/L, a polymer dissolution time of 3.5 hours, a target polymer solution concentration of 2000mg/L, a viscosity of 45 mPas at 25 ℃ and 7.34s-1, a viscosity of 21 mPas at 88 ℃ and 7.34s-1, a viscosity of 16 mPas at 95 ℃ and 7.34s-1, and a viscosity of 10 mPas at 100 ℃ and 7.34 s-1.
Comparative example 5
The polymerization process and procedure of example 1 were followed to replace poly (methacrylamidopropyltrimethylammonium chloride) with poly (oxyethylene) to obtain a temperature-resistant and salt-tolerant template-containing copolymer, and the other procedures were the same as in example 1. The temperature-resistant and salt-resistant copolymer obtained in comparative example 5 was tested in GB/T12005.10-92 using a Ubbelohde viscometer (0.55mm caliber) to obtain a viscosity average molecular weight of 1854 ten thousand.
The dry polymer powder obtained in comparative example 5 was dissolved in saline water having a total mineralization of 5.5X 104mg/L and a total calcium/magnesium ion concentration of 5500mg/L at 30 ℃ to prepare a polymer solution having a concentration of 5000mg/L, a polymer dissolution time of 3.0 hours, a target polymer solution concentration of 2000mg/L, a viscosity of 37 mPas at 25 ℃ and 7.34s-1, a viscosity of 18 mPas at 88 ℃ and 7.34s-1, a viscosity of 12 mPas at 95 ℃ and 7.34s-1, and a viscosity of 7 mPas at 100 ℃ and 7.34 s-1.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (10)
1. A preparation method of a temperature-resistant salt-resistant copolymer is characterized by comprising the following steps: sequentially adding water, an additive, acrylamide, a functional monomer and a template substance into a reactor, adding an inorganic base to adjust the pH value of a polymerization system, adding an initiator to initiate polymerization reaction, placing the polymerization system in an adiabatic environment, and stopping the reaction when the central temperature of the polymerization system is not increased to obtain a polymer colloid; crushing polymer colloid into colloidal particles, adding a hydrolytic agent for hydrolysis, drying, crushing and screening to obtain the polymer colloid; the template substance is polyacrylic acyloxy ethyl trimethyl ammonium chloride or polymethacrylamidopropyl trimethyl ammonium chloride, and the functional monomer is a sulfonic acid derivative containing terminal alkenyl and a sulfonate derivative thereof; the molar ratio of the template substance to the functional monomer is 0.1-1: 1; the molar ratio of the functional monomer to the acrylamide is 0.05-0.2: 1.
2. The method according to claim 1, wherein the molecular weight of the poly (acryloyloxyethyl trimethyl ammonium chloride) is 1000 to 20000; the molecular weight of the poly (methyl acrylamide propyl trimethyl ammonium chloride) is 1000-30000.
3. The method according to claim 1, wherein the terminal alkenyl group-containing sulfonic acid derivative and the sulfonate derivative thereof comprise: 2-acrylamido-2-methylpropanesulfonic acid and its sulfonates, vinylsulfonic acid and its sulfonates, and styrenesulfonic acid and its sulfonates.
4. The method of claim 1, wherein the additive comprises EDTA-2Na, urea, and sodium formate, wherein the EDTA-2Na is present in an amount of 0.002 wt% to 0.2 wt% based on the acrylamide concentration, the urea is present in an amount of 0.005 wt% to 10 wt% based on the acrylamide concentration, and the sodium formate is present in an amount of 0.001 wt% to 0.02 wt% based on the acrylamide concentration.
5. The preparation method according to claim 1, wherein the initiator is a redox system composed of an oxidant and a reducing agent, the oxidant is a persulfate, preferably, the persulfate is one selected from potassium persulfate and ammonium persulfate; the reducing agent is sulfite, preferably, the sulfite is selected from one of sodium bisulfite, sodium sulfite and sodium metabisulfite; the mass ratio of the oxidant to the reducer is 1:1, and the addition amount of the oxidant or the reducer is 0.01 wt% -0.2 wt% of the concentration of acrylamide.
6. The preparation method according to claim 1, wherein the acrylamide concentration is 10 wt% to 30 wt%, the pH value of the polymerization system is 5 to 7, and the initiation temperature is-5 ℃ to 30 ℃.
7. The preparation method according to claim 1, wherein the hydrolysis agent is added according to the degree of hydrolysis, wherein the degree of hydrolysis is 5-25%, and the hydrolysis agent is sodium hydroxide.
8. The preparation method according to claim 1, wherein the hydrolysis temperature is 80-110 ℃, the hydrolysis time is 1.0-4.0 h, the drying temperature is 90-110 ℃, and the drying time is 40 min-3 h.
9. The method of claim 1, wherein the polymer has a viscosity average molecular weight of 1000 to 2500 ten thousand.
10. The temperature-resistant and salt-resistant copolymer prepared by the preparation method of claims 1-8.
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| CN102060965A (en) * | 2009-11-11 | 2011-05-18 | 中国科学院理化技术研究所 | Preparation method of partially hydrolyzed polyacrylamide with improved temperature and salt resisting performances |
| CN104628943A (en) * | 2013-11-15 | 2015-05-20 | 中国石油化工股份有限公司 | Acrylamide copolymer, as well as preparation method and application thereof |
| US20180215852A1 (en) * | 2015-07-20 | 2018-08-02 | Sintef | Inverse Ugelstad Particles |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102060965A (en) * | 2009-11-11 | 2011-05-18 | 中国科学院理化技术研究所 | Preparation method of partially hydrolyzed polyacrylamide with improved temperature and salt resisting performances |
| CN104628943A (en) * | 2013-11-15 | 2015-05-20 | 中国石油化工股份有限公司 | Acrylamide copolymer, as well as preparation method and application thereof |
| US20180215852A1 (en) * | 2015-07-20 | 2018-08-02 | Sintef | Inverse Ugelstad Particles |
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