CN105237678A - Partially hydrolyzed acrylamide water-soluble polymer with utlralong hydrophobic long chain, preparation method therefor and application thereof - Google Patents
Partially hydrolyzed acrylamide water-soluble polymer with utlralong hydrophobic long chain, preparation method therefor and application thereof Download PDFInfo
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Abstract
The invention discloses a partially hydrolyzed acrylamide water-soluble polymer with an utlralong hydrophobic long chain, a preparation method therefor and an application thereof. A structural formula of the partially hydrolyzed acrylamide water-soluble polymer is as shown in formula II. The preparation method for the polymer as shown in formula II provided by the invention comprises the following steps: (1) under an inert atmosphere, dissolving acrylamide and docosyl polyoxyethylene ether methacrylate into water to obtain a solution I; (2) under the inert atmosphere, dissolving acrylic acid into water to obtain a solution II, and adding NaOH into the solution II to regulate the pH value of the system to 6-7; and (3) mixing solutions I and II obtained in the steps (1) and (2), and adding an initiator into the mixed solution to carry out a polymerization reaction, thereby obtaining the polymer. According to the preparation method provided by the invention, raw materials are easily available, preparation is simple, yield is relatively high, use is safe and storage is convenient. The partially hydrolyzed acrylamide water-soluble polymer with the utlralong hydrophobic long chain can be directly used, and has an extensive potential utilization value in the fields of oil exploitation, paint, medicines, daily use chemicals and the like.
Description
Technical field
The present invention relates to a kind of partial hydrolysis acrylamide water-soluble polymers and preparation method thereof and application, be specifically related to a kind of partial hydrolysis acrylamide water-soluble polymers containing the hydrophobic long-chain of overlength and preparation method thereof and application, belong to water-soluble polymer synthesis technical field.
Background technology
Partially hydrolyzed polyacrylamide (HPAM) is widely used in tertiary oil recovery due to its good water soluble characteristic.Hydroxy-acid group in HPAM can improve hydrodynamic volume by coulomb repulsion, but increases along with the electrolytical of small-molecular-weight, and worse and worse, the further application of HPAM is subject to a definite limitation to the underground environment in oil field.In order to improve the salt tolerance of HPAM, investigators have done the effort of two aspects: one is be devoted to synthesize the polyacrylamide or partially hydrolyzed polyacrylamide with ultra-high molecular weight, can improve the hydrodynamic volume of individual molecule chain like this; Two is carry out modification to partially hydrolyzed polyacrylamide, such as introduces hydrophobic monomer or introduces ionic group.
Summary of the invention
The object of this invention is to provide a kind of partial hydrolysis acrylamide water-soluble polymers containing the hydrophobic long-chain of overlength and preparation method thereof and application; Containing the hydrophobic backbone of overlength in polymkeric substance provided by the present invention, three-dimensional reciprocal networks structure can be formed after polymkeric substance is water-soluble, there is very strong stability, therefore there is excellent hydrophobic association performance and crude oil wettability and thick-oil emulsified adhesive-reducing performance, have a wide range of applications potentiality in fields such as oil production, coating, medicine and daily use chemicals.
Partial hydrolysis acrylamide water-soluble polymers containing the hydrophobic long-chain of overlength provided by the present invention, its structural formula such as formula shown in II,
In formula II, m/ (m+n+a)=89% ~ 90%, n/ (m+n+a)=9.6 ~ 10%, a/ (m+n+a)=0.1% ~ 1.0%;
The weight-average molecular weight M of described partial hydrolysis acrylamide water-soluble polymers
wbe 1.0 × 10
6gmol
-1~ 3.5 × 10
6gmol
-1.
In formula II, m/ (m+n+a)=89.3% ~ 89.9%, n/ (m+n+a)=9.64 ~ 10%, a/ (m+n+a)=0.1% ~ 0.65%;
The weight-average molecular weight M of described partial hydrolysis acrylamide water-soluble polymers
wbe 1.216 × 10
6gmol
-1~ 3.188 × 10
6gmol
-1.
Water-soluble polymers provided by the invention can be any one in following 4 kinds:
1) be polymkeric substance shown in formula II, in formula II, m/ (m+n+a)=89.90%, n/ (m+n+a)=10.00%, a/ (m+n+a)=0.10%; Weight-average molecular weight M
wbe 2.373 × 10
6gmol
-1;
2) be polymkeric substance shown in formula II, in formula II, m/ (m+n+a)=89.92%, n/ (m+n+a)=9.80%, a/ (m+n+a)=0.28%; Weight-average molecular weight M
wbe 2.74610
6gmol
-1;
3) be polymkeric substance shown in formula II, in formula II, m/ (m+n+a)=89.79%, n/ (m+n+a)=9.75%, a/ (m+n+a)=0.46%; Weight-average molecular weight M
wbe 3.188 × 10
6gmol
-1;
4) be polymkeric substance shown in formula II, in formula II, m/ (m+n+a)=89.71%, n/ (m+n+a)=9.64%, a/ (m+n+a)=0.65%; Weight-average molecular weight M
wbe 1.216 × 10
6gmol
-1.
Invention further provides the preparation method containing the partial hydrolysis acrylamide water-soluble polymers of the hydrophobic long-chain of overlength shown in formula II, comprise the steps:
(1) under an inert atmosphere, acrylamide and beheneth methacrylic ester (BEM) are dissolved in the water;
(2) under an inert atmosphere, vinylformic acid is soluble in water, and add pH value to 6 ~ 7 of NaOH regulation system;
(3) solution mixing step (1) and step (2) obtained, and add initiator, namely obtain polymkeric substance shown in formula II through polyreaction.
In above-mentioned preparation method, in step (1), the molar feed ratio of described acrylamide can be 89% ~ 90%, and the molar feed ratio of described beheneth methacrylic ester can be 0.5% ~ 1.0%;
Described molar feed ratio is a kind of ratio of feed intake mole number and monomer molar sum of monomer, and described monomer is described acrylamide, described beheneth methacrylic ester and described vinylformic acid.
The structural formula of beheneth methacrylic ester that the inventive method uses such as formula shown in I,
In above-mentioned preparation method, in step (2), described acrylic acid molar feed ratio can be 10%;
Described molar feed ratio is a kind of ratio of feed intake mole number and monomer molar sum of monomer, and described monomer is described acrylamide, described beheneth methacrylic ester and described vinylformic acid.
In above-mentioned preparation method, in step (3), in the system that step (1) and step (2) are mixed to get, the total concn of described monomer can be 1 ~ 2molL
-1, described monomer is described acrylamide, described beheneth methacrylic ester and described vinylformic acid.
In above-mentioned preparation method, in step (3), described initiator can be Potassium Persulphate or ammonium persulphate;
In the system that step (1) and step (2) are mixed to get, the add-on of described initiator can be 0.1 ~ 0.5mmolL
-1, specifically can be 0.11mmolL
-1;
Before described polyreaction, described method also comprises water bath with thermostatic control reaction system being placed in 20 ~ 28 DEG C, carries out the logical nitrogen deoxygenation step of 0.2 ~ 1 hour, as being placed in the water bath with thermostatic control of 25 DEG C, and letting nitrogen in and deoxidizing 0.5h.
In above-mentioned preparation method, in step (3), the temperature of described polyreaction is 40 ~ 80 DEG C, and the time can be 4 ~ 8 hours, as polyreaction 6h at 60 DEG C.
In above-mentioned preparation method, in step (3), after described polyreaction, described method also comprises the step precipitated the system after described polyreaction with acetone, what obtain after described polyreaction is the homogeneous mucus of oyster white, and this mucus precipitates in sewage acetone, then after filtration, through solid vacuum-drying, obtain the product of outer appearnce like white powder through pulverizing.
Partial hydrolysis acrylamide water-soluble polymers containing the hydrophobic long-chain of overlength shown in formula II provided by the invention can be used for preparing heavy crude thinner or crude oil wetting agent.
The hydrophobic monomer (BEM) that the present invention uses is surfactant monomer, and itself has surfactivity, can produce all (being total to) polyreactions under certain initiation conditions simultaneously.The novel partial hydrolysis acrylamide copolymer obtained is hydrophobic associated polymer (HAWP), containing the hydrophobic backbone of overlength in structure, can form three-dimensional reciprocal networks structure, have very strong stability after polymkeric substance is water-soluble.This makes it possess excellent heat resistance, has a wide range of applications potentiality in fields such as oil production, coating, medicine and daily use chemicals.
Do not need in polyreaction of the present invention to add emulsifying agent, therefore avoid in product and mix tensio-active agent and make product purity inadequate.In order to improve the heat-resistant salt-resistant of polymkeric substance, also introduce both sexes polymerization single polymerization monomers, its chemistry of this betaine type amphoteric monomer and Heat stability is good, hydratability are by force and be not subject to the impact of solution ph.
In sum, the present invention has the following advantages:
1, outstanding hydrophobic performance:
Containing the hydrophobic backbone of overlength in partial hydrolysis acrylamide water-soluble polymers provided by the invention, there is very strong hydrophobic association ability.
2, excellent heat resistance:
There is charged carboxylate radical in partial hydrolysis acrylamide water-soluble polymers provided by the invention, and contain the larger hydrophobic backbone of overlength of steric hindrance, the heat resistance of polymkeric substance can be improved.
3, in preparation method provided by the invention, polymeric reaction condition is gentle, and monomer conversion is high, and product last handling process is simple to operation.
4, the raw material of preparation method provided by the invention be easy to get, prepare simple, productive rate is higher, use safety, convenient storage.
5, the partial hydrolysis acrylamide water-soluble polymers containing the hydrophobic long-chain of overlength provided by the invention can directly use, and has potential utility value widely in fields such as oil production, coating, medicine and daily use chemicals.
Accompanying drawing explanation
Fig. 1 is the partial hydrolysis acrylamide water-soluble polymers containing the hydrophobic long-chain of overlength prepared by the embodiment of the present invention 1
1h-NMR spectrogram.
Fig. 2 is the change curve between the aqueous solutions of polymers of different concns in embodiment 6 and the contact angle of crude oil.
Embodiment
The experimental technique used in following embodiment if no special instructions, is ordinary method.
Material used in following embodiment, reagent etc., if no special instructions, all can obtain from commercial channels.
The specification of the raw material used in following embodiment is as follows:
Acrylamide, analytical pure, Tianjin Ke Miou chemical reagent company limited; Vinylformic acid, analytical pure, traditional Chinese medicines Group Co., Ltd; Beheneth methacrylic ester (BEM), purity is 50%, Sigma-Aldrich company; Sodium hydroxide, analytical pure, Tianjin Guang Cheng chemical reagent company limited; Potassium Persulphate (KPS), analytical pure, traditional Chinese medicines Group Co., Ltd; Acetone, analytical pure, Tianjin Fu Yu Fine Chemical Co., Ltd.
Embodiment 1, preparation contain the partial hydrolysis acrylamide water-soluble polymers of the hydrophobic long-chain of overlength
(1) 3.192 (0.045mol) acrylamides are taken and 0.150g (0.05mmol) hydrophobic monomer beheneth methacrylic ester is soluble in water.
(2) 0.36g (0.005mol) vinylformic acid is taken soluble in water, and with NaOH regulator solution pH value to 6 ~ 7.By the acrylic acid solution mixing of step (1) gained solution after neutralization, add and be equipped with in nitrogen tube, prolong and the there-necked flask with the 100mL of stirring magneton, under room temperature, logical nitrogen gas stirring is to dissolving completely;
(3) add initiator potassium persulfate (KPS) in the system obtained to step (2), be placed in the water bath with thermostatic control of 25 DEG C after stirring, letting nitrogen in and deoxidizing 0.5h; Relative to polymerization system volume, the add-on of Potassium Persulphate is 0.11mmolL
-1;
(4) system polyreaction 6h at 60 DEG C in step (3), after reaction terminates, obtains the homogeneous mucus of oyster white;
(5) using anhydrous propanone as precipitation solvent, the mucus obtained in step (3) is poured in acetone and precipitates, filter, by solid vacuum-drying, pulverize, obtain the partial hydrolysis acrylamide water-soluble polymers containing the hydrophobic long-chain of overlength shown in formula II.
Outward appearance is white powder, and quality is 3.505g, productive rate >=94%.
In formula II, m/ (m+n+a)=89.9%, n/ (m+n+a)=10%, a/ (m+n+a)=0.1%, records weight-average molecular weight M with multi-angle laser scattering of light
w=2.373 × 10
6gmol
-1.
Polymkeric substance prepared by the present embodiment
1h-NMR as shown in Figure 1, through qualification, proves that the product obtained is the partial hydrolysis acrylamide water-soluble polymers containing the hydrophobic long-chain of overlength.
Embodiment 2, preparation contain the partial hydrolysis acrylamide water-soluble polymers of the hydrophobic long-chain of overlength
Preparation method is in the same manner as in Example 1, difference is: in step (1), the charging capacity of acrylamide is 3.184g (0.0449mol), and the charging capacity of hydrophobic monomer beheneth methacrylic ester is 0.45g (0.15mmol); In step (2), acrylic acid charging capacity is 3.36g (0.005mol).
Containing the modified propylene acid amides water-soluble polymers powdery 3.724g of the hydrophobic long-chain of overlength shown in the formula of obtaining II, productive rate >=93%.
In formula II, m/ (m+n+a)=89.92%, n/ (m+n+a)=9.80%, a/ (m+n+a)=0.28%, weight-average molecular weight M
w=2.746 × 10
6gmol
-1.
Embodiment 3, preparation contain the partial hydrolysis acrylamide water-soluble polymers of the hydrophobic long-chain of overlength
Preparation method is in the same manner as in Example 1, difference is: in step (1), the charging capacity of acrylamide is 3.177g (0.04735mol), the charging capacity of hydrophobic monomer beheneth methacrylic ester is 0.75g (0.25mmol), and in step (2), acrylic acid charging capacity is 0.36g (0.005mol).
Containing the modified propylene acid amides water-soluble polymers powdery 3.946g of the hydrophobic long-chain of overlength shown in the formula of obtaining II, productive rate >=92%.
In formula II, m/ (m+n+a)=89.79%, n/ (m+n+a)=9.75%, a/ (m+n+a)=0.46%, weight-average molecular weight M
w=3.188 × 10
6gmol
-1.
Embodiment 4, preparation contain the partial hydrolysis acrylamide water-soluble polymers of the hydrophobic long-chain of overlength
Preparation method is in the same manner as in Example 1, difference is: in step (1), acrylamide charging capacity is 3.1702g (0.0447mol), the charging capacity of hydrophobic monomer beheneth methacrylic ester is 1.05g (0.35mmol), and in step (2), vinylformic acid charging capacity is 0.36g (0.005mol).
Containing the modified propylene acid amides water-soluble polymers powdery 4.028g of the hydrophobic long-chain of overlength shown in the formula of obtaining II, productive rate >=91%.
In formula II, m/ (m+n+a)=89.71%, n/ (m+n+a)=9.64%, a/ (m+n+a)=0.65%, weight-average molecular weight M
w=1.216 × 10
6gmol
-1.
Experimental example 5, heat resistance are tested
That embodiment 1 is prepared carries out heat resistance test containing the partial hydrolysis acrylamide water-soluble polymers of the hydrophobic long-chain of overlength, experiment condition and step as follows:
This experiment MettlerToledoSDTA-851 type thermal analyzer measures the thermal weight loss character of polymkeric substance.
Sample is loaded crucible and compacting and hangs on thermogravimetric analysis balance and weigh, carry out intensification test.
This experiment test carries out in high pure nitrogen atmosphere, and nitrogen flow is about 50mL.min
-1.Range of measuring temp is 25-600 DEG C, and the temperature rise rate of test process is 20 DEG C of .min
-1.
Learn after tested, the partial hydrolysis acrylamide water-soluble polymers containing the hydrophobic long-chain of overlength prepared by embodiment 1 has higher thermostability, and the thermal degradation temperature of main polymer chain is increased to 420 DEG C.
Experimental example 6, crude oil wettability are tested
That embodiment 2 and embodiment 3 are prepared carries out the test of crude oil wettability containing the partial hydrolysis acrylamide water-soluble polymers of the hydrophobic long-chain of overlength, experiment condition and step as follows:
The CONTACTANGLESYSTEMOCA contact angle measurement that this experiment adopts German DATAPHYSICS to produce is measured.
This experiment acetone cleans up slide glass, is coated with one deck crude oil, leaves standstill 12h, make crude oil spread on the surface of slide glass equably, measure the wettability of polymers soln and crude oil on its surface.
Fig. 2 is the change curve between the aqueous solutions of polymers of different concns and the contact angle of crude oil, PAAB-2 and PAAB-3 in figure represents the polymkeric substance of embodiment 2 and embodiment 3 preparation respectively.
As shown in Figure 2, the partial hydrolysis acrylamide water-soluble polymers containing the hydrophobic long-chain of overlength that prepared by embodiment 2 and embodiment 3 at room temperature has good crude oil wettability; When the concentration of the aqueous solution is 0.1mg/mL, test shows that the contact angle of sample and crude oil is 25 °, and when concentration of aqueous solution is increased to 1.75mg/mL, contact angle can drop to 14 °.
Experimental example 7, reducing thick oil viscosity are tested
That embodiment 2 and embodiment 3 are prepared carries out reducing thick oil viscosity test containing partial hydrolysis acrylamide water-soluble polymers PAAB-2 and PAAB-3 of the hydrophobic long-chain of overlength, experiment condition and step as follows:
This experiment adopts BrookfieldDV-II+ viscometer (rotor is SC4-31) to measure emulsion of crude oil viscosity under reservoir conditions; Experimental viscosity value probe temperature is 50 DEG C, and shearing rate is 10.2s
-1.
This experiment changes the concentration of polymkeric substance and volume, is mixed to get milk sap with crude oil, probes into the concentration of synthesized PAAB series polymer solution and different water-oil ratio to the impact of Reducing Viscosity by Emulsifying for Crude Oil character.
Table 1 is the viscosity of crude change under adding of different concns aqueous solutions of polymers, and when table 2 is different volumes profit proportioning, the viscosity B coefficent of crude oil, wherein PAAB-2 represents polymkeric substance prepared by embodiment 2, and PAAB-3 represents polymkeric substance prepared by embodiment 3.
From table 1 and table 2, polymkeric substance prepared by the present invention has good thick-oil emulsified adhesive-reducing ability.When not adding polymkeric substance, viscosity of thickened oil is 1400mPa.s, and when polymer concentration reaches 1.75g/L, embodiment 2 viscosity of thickened oil is 101mPa.s, and embodiment 3 viscosity of thickened oil is 93mPa.s; When water-oil ratio (volume ratio) is for 3:2, embodiment 2 viscosity of thickened oil is 165mPa.s, and embodiment 3 viscosity of thickened oil is 151mPa.s.
Viscosity of crude change under the adding of table 1 different concns aqueous solutions of polymers
| Polymer concentration (g/L) | Add PAAB-2 | Add PAAB-3 |
| 0 | 1440 | 1440 |
| 0.5 | 332 | 299 |
| 0.75 | 288 | 255 |
| 1 | 181 | 170 |
| 1.5 | 126 | 129 |
| 1.75 | 101 | 93 |
When table 2 different volumes profit proportioning, the viscosity B coefficent of crude oil
| Different water-oil ratio | Add PAAB-2 | Add PAAB-3 |
| Viscous crude | 1440 | 1440 |
| 1:4 | 532 | 497 |
| 2:3 | 442 | 434 |
| 1:1 | 332 | 299 |
| 3:2 | 165 | 151 |
Claims (10)
1. containing the partial hydrolysis acrylamide water-soluble polymers of the hydrophobic long-chain of overlength, its structural formula such as formula shown in II,
In formula II, m/ (m+n+a)=89% ~ 90%, n/ (m+n+a)=9.6 ~ 10%, a/ (m+n+a)=0.1% ~ 1.0%;
The weight-average molecular weight M of described partial hydrolysis acrylamide water-soluble polymers
wbe 1.0 × 10
6gmol
-1~ 3.5 × 10
6gmol
-1.
2. contain the preparation method of the partial hydrolysis acrylamide water-soluble polymers of the hydrophobic long-chain of overlength shown in formula II, comprise the steps:
(1) under an inert atmosphere, acrylamide and beheneth methacrylic ester are dissolved in the water;
(2) under an inert atmosphere, vinylformic acid is soluble in water, and add pH value to 6 ~ 7 of NaOH regulation system;
(3) solution mixing step (1) and step (2) obtained, and add initiator, namely obtain polymkeric substance shown in formula II through polyreaction.
3. preparation method according to claim 2, it is characterized in that: in step (1), the molar feed ratio of described acrylamide is 89% ~ 90%, and the molar feed ratio of described beheneth methacrylic ester is 0.1% ~ 1.0%;
Described molar feed ratio is a kind of ratio of feed intake mole number and monomer molar sum of monomer, and described monomer is described acrylamide, described beheneth methacrylic ester and described vinylformic acid.
4. the preparation method according to Claims 2 or 3, is characterized in that: in step (2), and described acrylic acid molar feed ratio is 9.6 ~ 10%;
Described molar feed ratio is a kind of ratio of feed intake mole number and monomer molar sum of monomer, and described monomer is described acrylamide, described beheneth methacrylic ester and described vinylformic acid.
5. the preparation method according to any one of claim 2-4, is characterized in that: in step (3), and in the system that step (1) and step (2) are mixed to get, the total concn of described monomer is 1 ~ 2molL
-1, described monomer is described acrylamide, described beheneth methacrylic ester and described vinylformic acid.
6. the preparation method according to any one of claim 2-5, is characterized in that: in step (3), and described initiator is Potassium Persulphate or ammonium persulphate;
In the system that step (1) and step (2) are mixed to get, the add-on of described initiator is 0.1 ~ 0.5mmolL
-1;
Before described polyreaction, described method also comprises water bath with thermostatic control reaction system being placed in 20 ~ 28 DEG C, carries out the logical nitrogen deoxygenation step of 0.2 ~ 1 hour.
7. the preparation method according to any one of claim 2-6, is characterized in that: in step (3), and the temperature of described polyreaction is 40 ~ 80 DEG C, and the time is 4 ~ 8 hours.
8. the preparation method according to any one of claim 2-7, is characterized in that: in step (3), after described polyreaction, described method also comprises the step precipitated the system after described polyreaction with acetone.
9. the partial hydrolysis acrylamide water-soluble polymers containing the hydrophobic long-chain of overlength shown in formula II is preparing the application in heavy crude thinner or crude oil wetting agent.
10. heavy crude thinner or a crude oil wetting agent, its activeconstituents is the partial hydrolysis acrylamide water-soluble polymers containing the hydrophobic long-chain of overlength shown in formula II.
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Address after: 100010 Beijing, Chaoyangmen, North Street, No. 25, No. Applicant after: China Offshore Oil Group Co., Ltd. Applicant after: CNOOC research institute limited liability company Address before: 100010 Beijing, Chaoyangmen, North Street, No. 25, No. Applicant before: China National Offshore Oil Corporation Applicant before: CNOOC Research Institute |
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Application publication date: 20160113 |