CN105884980B - A kind of fluorine-containing hyperbranched multi-arm polyacrylamide polymer - Google Patents
A kind of fluorine-containing hyperbranched multi-arm polyacrylamide polymer Download PDFInfo
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Abstract
The invention discloses a kind of fluorine-containing hyperbranched multi-arm polyacrylamide polymers.Its structural formula is as shown in formula I, wherein core A is the hyperbranched polyglycidyl ether of end group hydroxyl；Arm B is the copolymer formed by acrylamide, sodium acrylate, fluorine-containing hydrophobic monomer and amphoteric ion choline function monomer；In copolymer, polyacrylamide segment, Sodium Polyacrylate segment, poly- fluorine-containing hydrophobic segment and poly- amphoteric ion choline function segment are sequentially connected, and the other end of polyacrylamide segment is grafted on core A.The fluorine-containing hyperbranched multi-arm polyacrylamide polymer of the present invention is copolymerized by hyperbranched polyglycidyl ether spherical shape parent nucleus, acrylamide, sodium acrylate, fluorine-containing hydrophobic monomer, amphoteric ion choline function monomer.The anti-shear performance of polymer can be improved in the spherical hyperbranched multi-arm structure of the 3 D stereo of Inventive polymers and fluorine-containing hydrophobic segment, and amphoteric ion choline function segment assigns the good anti-salt property of polymer.
Description
Technical field
The present invention relates to a kind of fluorine-containing hyperbranched multi-arm polyacrylamide polymers, belong to polymeric material field.
Background technology
Enhancing oil recovery in polymer flooding technology is one of the important measures of oil field sustainable development.The North Sea oil fields CAPtain,
The oil fields India Sanand and Venezuela, Russia, the U.S., etc. successfully carried out polymer displacement of reservoir oil, domestic grand celebration, triumph,
Henan, Bohai Bay Oil etc. have also carried out large-scale application, have been achieved for significant water-control oil-increasing effect at present.Polymer displacement of reservoir oil
System is core and the basis of polymer displacement of reservoir oil tech, and it is partially hydrolyzed polyacrylamide (PHPA) Type of Collective to be most widely used at present
Object.With going deep into for oil field development, the reservoir media of polymer displacement of reservoir oil tech application is also by preferably a kind of oil reservoir of condition, gradually
Change to two, three classes oil reservoir, therefore polyacrylamide polymer also gradually faces salt resistance, anti-shearing, anti-oxidant and heat resistanceheat resistant drop
The problem of performances such as solution cannot be satisfied demand.
On the basis of partially hydrolyzed polyacrylamide (PHPA), by improving molecular structure or introducing function segment, it can be obtained all
More modified products, as amphoteric ion polymer, the monomer modified polymer of temperature-resistant anti-salt, hydrophobic associated polymer, comb-shaped polymer,
Star-type polymer and polymer complex etc. are all greatly increased in heat-resistant salt-resistant performance.But due to big
More modified products, agent structure are still the linear chain structure of polyacrylamide, and under high shear conditions, structural instability is held
It is easily destroyed, viscosity is caused drastically to decline, finally influence polymer flooding effect.The linear chain structure for improving polymer is to improve polymer
The important channel of anti-shear performance.
Invention content
It is provided by the invention to contain the object of the present invention is to provide a kind of fluorine-containing hyperbranched multi-arm polyacrylamide polymer
The hyperbranched multi-arm polyacrylamide polymer of fluorine has stronger anti-shear performance and anti-salt property.
Present invention firstly provides a kind of preparation methods of the hyperbranched polyglycidyl ether (HPG) of end group hydroxyl, including
Following steps：
Glycidol carries out ring-opening polymerization under conditions of total initiation system to obtain the final product；
It is described to cause the mixture that system is 1,1,1- trimethylolpropanes and potassium methoxide altogether.
In above-mentioned preparation method, described 1,1,1- trimethylolpropane, the potassium methoxide and the glycidol matter
Amount is than that can be 1：0.11~0.13：130~170, concretely 1：0.12：169；
The temperature of the ring-opening polymerization can be 90~100 DEG C, and the time can be 10~15 hours, such as in 95 DEG C of condition
Lower reaction 15 hours.
The hyperbranched polyglycidyl ether for the end group hydroxyl that the above method is prepared also belongs to the protection model of the present invention
It encloses.
The molecular formula of the hyperbranched polyglycidyl ether of the end group hydroxyl is (C3H8O3)m, between wherein m is 7~12
Integer, as m be 9；
The branch rate of the hyperbranched polyglycidyl ether of the end group hydroxyl can be 0.5~0.6, concretely 0.6.
Hyperbranched multi-arm polyacrylamide can be prepared by core of the hyperbranched polyglycidyl ether of the end group hydroxyl
Polymer, to improve the anti-shear performance of polymer.
Fluorine-containing hyperbranched multi-arm polyacrylamide polymer provided by the present invention, structural formula is as shown in formula I：
Wherein, core A is the hyperbranched polyglycidyl ether of the end group hydroxyl；
Arm B is to be total to by what acrylamide, sodium acrylate, fluorine-containing hydrophobic monomer and amphoteric ion choline function monomer were formed
Polymers；
In the copolymer, polyacrylamide segment, gathers fluorine-containing hydrophobic segment and poly- amphoteric ion at Sodium Polyacrylate segment
Choline function segment is sequentially connected, and the other end of the polyacrylamide segment is grafted on the core A.
In above-mentioned fluorine-containing hyperbranched multi-arm polyacrylamide polymer, the fluorine-containing hyperbranched multi-arm polyacrylamide
The viscosity average molecular weigh of Type of Collective object is 3,000,000~8,000,000, such as 8,000,000；
The core A, the polyacrylamide segment, the Sodium Polyacrylate segment, the poly- fluorine-containing hydrophobic segment and institute
The mass ratio for stating poly- amphoteric ion choline function segment can be 1：200~300：50~70：10~15：10~15, concretely
1：270：60~63：12~13：10~12,1：270：60：13：10 or 1：270：63：12：12.
In above-mentioned fluorine-containing hyperbranched multi-arm polyacrylamide polymer, the fluorine-containing hydrophobic monomer can be acrylic acid six
Fluorine butyl ester, Hexafluorobutyl mathacrylate, ten trifluoro monooctyl ester of methacrylic acid, dodecafluorhe-ptylacrylate, methacrylic acid ten
At least one of difluoro heptyl ester and trifluoroethyl methacrylate；
The amphoteric ion choline function monomer can be shown in methylacryloyl phosphocholine or formula III shown in formula II
Methacryl yl carboxylic acid choline：
In formula III, n is the number between 1~3.
The fluorine-containing hyperbranched multi-arm polyacrylamide polymer of the present invention can be prepared by the following method：
(1) under an inert atmosphere, the hyperbranched polyglycidyl ether of the end group hydroxyl and redox initiator into
Row reaction, obtains reaction solution 1；
(2) it is slowly added to the acrylamide monomer, sodium acrylate monomers, described successively into the reaction solution 1
Fluorine-containing hydrophobic monomer, the amphoteric ion choline function monomer carry out graft copolymerization to get the polymer.
In above-mentioned preparation method, in step (1), the redox initiator can be selected from following at least one：Nitric acid
Cerium ammonium, potassium peroxydisulfate, ammonium persulfate, sodium peroxydisulfate and hydrogen peroxide；
The redox initiator participates in reacting in the form of its aqueous solution, in the aqueous solution, the redox
The mass percent concentration of initiator can be 0.5%~2%, concretely 0.5%；
The mass ratio of the redox initiator and the hyperbranched polyglycidyl ether of the end group hydroxyl can be 1.5
~2.5：1, concretely 1.42~1.7：1、1.42：1 or 1.7：1；
The temperature of the reaction can be 30~50 DEG C, and the time can be 30~60min, such as react 30min at 40 DEG C.
In above-mentioned preparation method, in step (2), the acrylamide monomer is in the form of acrylamide monomer aqueous solution
It being added, the mass percent concentration of the acrylamide monomer aqueous solution can be 25~35%, concretely 31%；
The sodium acrylate monomers are added in the form of sodium acrylate monomers aqueous solution, the sodium acrylate monomers aqueous solution
Mass percent concentration can be 15~25%, concretely 21%；
The fluorine-containing hydrophobic monomer is added in the form of emulsion, the emulsion using lauryl sodium sulfate and water into
Row is prepared, and in the emulsion, the mass percent concentration of the fluorine-containing hydrophobic monomer can be 4~12%, and concretely 8.3%
~10%, 8.3% or 10%；
The amphoteric ion choline function monomer is added in the form of amphoteric ion choline function monomer aqueous solution, institute
The mass concentration for stating amphoteric ion choline function monomer aqueous solution can be 6~12%, concretely 8.3%；
The hyperbranched polyglycidyl ether of the end group hydroxyl, the acrylamide monomer, the sodium acrylate monomers,
The mass ratio of the fluorine-containing hydrophobic monomer and the amphoteric ion choline function monomer can be 1：250~350：50~80：10~
30：5~15, concretely 1：300：70：115：12；
The temperature of the graft copolymerization can be 45~75 DEG C, and the time can be 5~10h, such as react 6h at 55 DEG C.
The method further includes the withering step of reaction system to step (2), such as at 60~80 DEG C (70
DEG C) baking oven in be dried.
The fluorine-containing hyperbranched multi-arm polyacrylamide polymer of the present invention can be used as oil displacement agent for the field polymers displacement of reservoir oil
In, configuration concentration range can be 1200~3000mg/L, such as 1750mg/L.
The fluorine-containing hyperbranched multi-arm polyacrylamide polymer of the present invention is by hyperbranched polyglycidyl ether spherical shape parent nucleus, third
Acrylamide, sodium acrylate, fluorine-containing hydrophobic monomer, amphoteric ion choline function monomer are copolymerized.The present invention is fluorine-containing hyperbranched
Polymerization can be improved in the spherical hyperbranched multi-arm structure of the 3 D stereo of multi-arm polyacrylamide polymer and fluorine-containing hydrophobic segment
The anti-shear performance of object, amphoteric ion choline function segment assign the good anti-salt property of polymer.
Description of the drawings
Fig. 1 is the thickening property figure of hyperbranched multi-arm polyacrylamide polymer prepared by the present invention.
Fig. 2 is the anti-salt property figure of hyperbranched multi-arm polyacrylamide polymer prepared by the present invention.
Fig. 3 is the anti-shear performance figure of hyperbranched multi-arm polyacrylamide polymer prepared by the present invention.
Specific implementation mode
Experimental method used in following embodiments is conventional method unless otherwise specified.
The materials, reagents and the like used in the following examples is commercially available unless otherwise specified.
Methylacryloyl phosphorylcholine-monomer employed in following embodiments is drug Co., Ltd of Sigma of the U.S.
Product, reagent abridge MPC, CAS accession number is 67881-98-5.
The product of drug Co., Ltd of Sigma of the methacryl yl carboxylic acid choline U.S. employed in following embodiments,
Reagent abbreviation CBMA, CAS accession number is 24249-95-4, wherein n=1.
Hexafluorobutyl mathacrylate employed in following embodiments is to avenge good fluorine chemistry of silicones Products, reagent abbreviation
HFBMA, CAS registration number are 36405-47-7.
Embodiment 1, the polyglycidyl ether HPG for preparing end group richness hydroxyl
1,1,1- trimethylolpropane (TMP) (0.187g, 1.39mmol) is added in three-necked flask, is then added dropwise
The methanol solution (potassium methoxide containing 22mg) of the 20wt% potassium methoxides of 0.11mL reacts 20min, methanol is removed in vacuum, adds nothing
Water dioxane 20mL.Temperature rises to 95 DEG C, is slowly added to very much the glycidol (about 10h completions) of 25mL (31.6g).It is added
After, a large amount of methanol is added in the reaction was continued 5h, and excessively cationic pillar removes K+, with a large amount of acetone precipitation methanol solution
White solid HPG is obtained, suction filtration, vacuum freezedrying obtain product HPG (m=8~10), and molecular formula is (C3H8O3)m, wherein m is 9,
Branch rate is 0.6.
Embodiment 2 prepares fluorine-containing hyperbranched multi-arm polyacrylamide polymer
By 30mg HPG, 85mL H2O is placed in three-necked flask, stirring and dissolving, nitrogen deoxygenation 45min is passed through, then in nitrogen
Ammonium ceric nitrate aqueous solution (50mg ammonium ceric nitrates are dissolved in 10mL) is added under gas shielded, 30min is stirred to react at 40 DEG C, to reaction solution
In be slowly added to acrylamide aqueous solution (9.0g acrylamides are dissolved in 20mL water), aqueous sodium acrylate solution (2.1g third successively
Olefin(e) acid sodium is dissolved in 8mL water), Hexafluorobutyl mathacrylate monomer emulsion (450mg Hexafluorobutyl mathacrylates monomers breast
Change is dissolved in 5mL water, and emulsifier is lauryl sodium sulfate 450mg), acryloyl group phosphorylcholine-monomer aqueous solution (360mg third
Enoyl- phosphorylcholine-monomer is dissolved in 4mL water), then it is warming up to 55 DEG C of reaction 6h.Gained reaction solution is placed in 70 DEG C of baking ovens
Interior drying goes moisture removal to get the fluorine-containing hyperbranched multi-arm polyacrylamide polymers of 1#, and viscosity average molecular weigh is about 8,000,000.
In the fluorine-containing hyperbranched multi-arm polyacrylamide polymers of 1# manufactured in the present embodiment, HPG, polyacrylamide segment,
The mass ratio of Sodium Polyacrylate segment, polymethylacrylic acid hexafluoro butyl ester segment and polypropylene acyl group phosphocholine segment is 1：
270：60：13：10.
Embodiment 3 prepares fluorine-containing hyperbranched multi-arm polyacrylamide polymer
By 35mg HPG, 85mL H2O is placed in three-necked flask, stirring and dissolving, nitrogen deoxygenation 45min is passed through, then in nitrogen
Ammonium ceric nitrate aqueous solution (50mg ammonium ceric nitrates are dissolved in 10mL water) is added under gas shielded, is stirred to react 30min at 40 DEG C, to anti-
It answers and is slowly added to acrylamide aqueous solution (10.5g acrylamides are dissolved in 23.4mL water), aqueous sodium acrylate solution in liquid successively
(2.45g sodium acrylate is dissolved in 9.4mL water), Hexafluorobutyl mathacrylate monomer emulsion (525mg methacrylic acid hexafluoros
Butyl ester monomer is emulsifiable in 5.8mL water, and emulsifier is lauryl sodium sulfate 525mg), acryloyl group carboxylic acid choline monomer is water-soluble
Liquid (420mg acryloyl group carboxylic acid choline monomers are dissolved in 4.6mL water) is then warming up to 55 DEG C of reaction 6h.By gained reaction solution
Being placed in drying in 70 DEG C of baking ovens goes moisture removal to get the fluorine-containing hyperbranched multi-arm polyacrylamide polymers of 2#, viscosity average molecular weigh
About 8,000,000.
In the fluorine-containing hyperbranched multi-arm polyacrylamide polymers of 2# manufactured in the present embodiment, HPG, polyacrylamide segment,
The mass ratio of Sodium Polyacrylate segment, polymethylacrylic acid hexafluoro butyl ester segment and polyacrylamide yl carboxylic acid choline segment is 1：
270：63：12：12.
The performance test of embodiment 4, fluorine-containing hyperbranched multi-arm polyacrylamide polymer
The performance of the 1# and the fluorine-containing hyperbranched multi-arm polyacrylamide polymers of 2# of the invention prepared is evaluated, is evaluated
Method and result are as follows, and wherein unaltered portion hydrolyzed polyacrylamide (i.e. " general polymer ") is industrialization product, quotient
Product model FP6050, is purchased from SNF companies of France, and structure is linear straight chain type.
(1) thickening property：A certain amount of polymer is taken, under 45 DEG C of water bath conditions, various concentration is prepared with deionized water
Polymer solution, the relationship of test polymer viscosity and concentration evaluates the thickening property of polymer, and the results are shown in Figure 1, and
It is compared with unaltered portion hydrolyzed polyacrylamide performance.
As shown in Figure 1, with the increase of concentration, 1# and the fluorine-containing hyperbranched multi-arm polyacrylamide polymers aqueous solutions of 2#
Viscosity dramatically increases, and as a concentration of 1500mg/L, viscosity can be up to 85.0 and 95.0mPas respectively, far above under concentration
The 51.7mPas of unaltered portion hydrolyzed polyacrylamide.
(2) anti-salt property：A certain amount of polymer is taken, is 9374.12mg/L mines with salinity under 45 DEG C of water bath conditions
Change water, ion group is as (unit mg/L)：Na++K+(3091.96)、Ca2+(276.17)、Mg2+(168.68)、CO3 2-
(14.21)、HCO3 -(311.48)、SO4 2-(85.29)、Cl-(5436.34), the relationship of test polymer viscosity and concentration, evaluation
The anti-salt property of polymer, the results are shown in Figure 2, and is compared with unaltered portion hydrolyzed polyacrylamide performance.
As shown in Figure 2, the fluorine-containing dissaving polymers of 1# and 2# still maintain higher in 9374.12mg/L mineralized waters
Viscosity.In concentrated water, when polymer concentration is 1500mg/L, 1# and the hyperbranched multi-arm polyacrylamide polymers of 2#
Viscosity is respectively 27.3 and 30.6mPas, far above unaltered portion hydrolyzed polyacrylamide under comparable sodium
10.1mPa·s。
(3) anti-shear performance：It is the polymer solution of 1500mg/L to take aimed concn, with the 1 grade of shearing of Rhein blender
20s measures the apparent viscosity before and after polymeric shear, calculates viscosity retention ratio, the results are shown in Figure 3, and and unaltered portion
Hydrolyzed polyacrylamide performance is compared.
From the figure 3, it may be seen that in concentrated water, after 1# and the fluorine-containing dissaving polymer solution of 2# are clipped, viscosity retains
Rate is maintained at 60% or more, is higher than 40% or so of unaltered portion hydrolyzed polyacrylamide.
(4) Oil Displacing Capacity：It is the polymer solution of 1750mg/L, one grade of shearing 20s of Waring blenders to take aimed concn
It is spare afterwards.Use for laboratory artificial core, gas permeability are respectively 500,2000 and 4000mD from top to bottom.With Bohai Sea oil field
Simulation oil is compounded after comprehensive oil sample dehydration with kerosene, 65 DEG C of viscosity are 70mPas.First carry out water drive, moisture content is up to 98% or more
When turn polymer flooding.Polymer and water drive velocity are 3m/d, and polymer solution injected slurry volume is 0.3PV.The experimental results showed that
The oil-recovering rate of 1# and the fluorine-containing dissaving polymer solution of 2# can be improved 10 than unaltered portion hydrolyzed polyacrylamide~
15%, it can be seen that the fluorine-containing dissaving polymer of the present invention has preferable oil-displacement capacity.
In conclusion dissaving polymer of the present invention be demonstrated by the thickening better than unaltered portion hydrolyzed polyacrylamide,
Salt resistance, anti-shearing and Oil Displacing Capacity, can be used as polymer oil-displacing agent.
Claims (1)
1. a kind of fluorine-containing hyperbranched multi-arm polyacrylamide polymer, structural formula is as shown in formula I：
Wherein, core A is the hyperbranched polyglycidyl ether of end group hydroxyl；
The molecular formula of the hyperbranched polyglycidyl ether of the end group hydroxyl is (C3H8O3)m, wherein m be 7~12 between it is whole
Number；
The branch rate of the hyperbranched polyglycidyl ether of the end group hydroxyl is 0.5~0.6；
The hyperbranched polyglycidyl ether of the end group hydroxyl is prepared according to the method included the following steps：
Glycidol carries out ring-opening polymerization under conditions of total initiation system to obtain the final product；
It is described to cause the mixture that system is 1,1,1- trimethylolpropanes and potassium methoxide altogether；
The mass ratio of the 1,1,1- trimethylolpropanes, the potassium methoxide and the glycidol is 1：0.11~0.13：130
~160；
The temperature of the ring-opening polymerization is 90~100 DEG C, and the time is 10~15 hours；
Arm B is the copolymerization formed by acrylamide, sodium acrylate, fluorine-containing hydrophobic monomer and amphoteric ion choline function monomer
Object；
In the copolymer, polyacrylamide segment, gathers fluorine-containing hydrophobic segment and poly- amphoteric ion choline at Sodium Polyacrylate segment
Function segment is sequentially connected, and the other end of the polyacrylamide segment is grafted on the core A；
The viscosity average molecular weigh of the fluorine-containing hyperbranched multi-arm polyacrylamide polymer is 3,000,000~8,000,000；
The core A, the polyacrylamide segment, the Sodium Polyacrylate segment, the fluorine-containing hydrophobic segment and described poly- of gathering
The mass ratio of amphoteric ion choline function segment is 1：200~300：50~70：10~15：10~15；
The fluorine-containing hydrophobic monomer be hexafluorobutyl acrylate, Hexafluorobutyl mathacrylate, ten trifluoro monooctyl ester of methacrylic acid,
At least one of dodecafluorhe-ptylacrylate, dodecafluoroheptyl methacrylate and trifluoroethyl methacrylate；
The amphoteric ion choline function monomer is glycine betaine shown in methylacryloyl phosphocholine or formula III shown in formula II
Class monomer：
In formula III, n is the number between 1~3.
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| CN101519473A (en) * | 2009-03-31 | 2009-09-02 | 山东大学 | Method for preparing fluorine-containing modified amphoteric water-soluble polymer |
| EP2604636A1 (en) * | 2011-12-15 | 2013-06-19 | Stichting Dutch Polymer Institute | Enhanced oil recovery using polyacrylamides |
| CN104844766A (en) * | 2015-05-18 | 2015-08-19 | 中国海洋石油总公司 | Hyperbranched multi-arm polyacrylamide polymer and preparation method thereof |
| CN105542070A (en) * | 2015-12-29 | 2016-05-04 | 四川光亚聚合物化工有限公司 | Hydrophobic association polymer and preparation method thereof |
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| CN101519473A (en) * | 2009-03-31 | 2009-09-02 | 山东大学 | Method for preparing fluorine-containing modified amphoteric water-soluble polymer |
| EP2604636A1 (en) * | 2011-12-15 | 2013-06-19 | Stichting Dutch Polymer Institute | Enhanced oil recovery using polyacrylamides |
| CN104844766A (en) * | 2015-05-18 | 2015-08-19 | 中国海洋石油总公司 | Hyperbranched multi-arm polyacrylamide polymer and preparation method thereof |
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