Startseite Design, synthesis, and characterization of novel copolymer gel particles for water-plugging applications
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Design, synthesis, and characterization of novel copolymer gel particles for water-plugging applications

  • Ding-Jun Zhang , Mei-Ju Zhang EMAIL logo , Zhan-Dong Luo und Sheng-Xiang Zhang
Veröffentlicht/Copyright: 18. September 2024
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e-Polymers
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Abstract

Multi-stage plugging represents a promising strategy for enhancing production and injection rates in medium-and low-permeability oilfields. Despite its potential, the efficacy of current plugging agents, particularly hydrophobically bonded water-soluble polyacrylamide-based gel microspheres, is hindered by notable drawbacks such as low stability and inadequate compressive strength. Therefore, a comprehensive understanding of water plugging mechanisms coupled with the optimization of gel microsphere properties is essential for advancing the development of gel-based plugging agents with superior characteristics or intelligent regulatory capabilities. The P(AA-AM-[PrSO3]Vim) ionic liquid copolymerized gel particles were designed and synthesized by using microfluidic technique and titration gel method with AM, acrylic acid (AA), 1-vinylimidazole (Vim) and 1,3-propylsulfonyl lactone (PrSO3) as the raw materials. The morphology and structure of the copolymer gel particles were characterized, and the effects of [PrSO3]Vim and cross-linker content on the water-absorbing properties and strength of the gel particles were investigated. When the amount of [PrSO3]Vim was 12%, the concentration of crosslinker was 1.5%, and the temperature was 40°C, the water absorption capacity reached the maximum value of 163 g·g−1. The strength of the P(AA–AM–[PrSO3]Vim) spherical gel particles was maximized at a [PrSO3]Vim content of 4%. Furthermore, the chemical and physical roles of the P(AA–AM–[PrSO3]Vim) spherical gel particles were studied in a typical water-plugging environment. This study provides experimental data and a theoretical basis for the application of functional spherical gel-plugging particles in current oilfield environments.

Keywords: functional ionic liquids; ionic liquids polymer; copolymerization reaction; green chemistry

1 Introduction

In recent years, oilfield operations have progressed into the middle and late stages of extraction. However, the main producing oilfields are now threatened with extraction problems such as formation of high water content, increased complexity of the oil core, and increased formation temperatures, which not only reduce the rate of extraction from oilfields but also cause environmental pollution and reduce the economic returns of oilfields (1,2). During the course of oilfield development, the internal environment of the formation becomes increasingly intricate due to prolonged water injection. To address these complexities, particularly in moderate and low permeability oilfields, it becomes imperative to modify deep water flow channels, implement deep multi-stage plugging, enhance water drive development efficacy, and augment the temperature resistance, salt tolerance, and stability of oil displacement polymers. Such interventions are crucial for augmenting oilfield production rates and ensuring sustainable development amidst evolving operational challenges (3,4). The prevailing plugging agents consist of hydrophobically bonded water-soluble polyacrylamide (PAM)-based gel microspheres, known for their notable attributes including high viscosity, favorable solubility, and cost-effectiveness. However, these gel plugging agents exhibit weaknesses such as poor stability and low compressive strength, primarily attributed to the presence of amide and carboxyl groups within the molecular chain. The susceptibility of the amide group to high-temperature hydrolysis and the salt sensitivity of the carboxyl group contribute to a decrease in the viscosity of the plugging agent (5). Consequently, the PAM-based gel plugging agent demonstrates inadequate resistance to temperature, salt, and shear, thus imposing limitations on its application environment (6,7). Utilizing acrylamide (AM) and acrylic acid (AA) as monomers along with the incorporation of a crosslinking agent inevitably imposes limitations on the temperature resistance, gel strength, and stability of the resulting gel plugging agent. Moreover, during application, as the temperature rises, the degradation of the gel accelerates, leading to a rapid decline in gel strength, ultimately compromising its plugging and regulatory efficacy. To enhance compressive strength, temperature resistance, salt tolerance, and overall stability across diverse deployment scenarios, researchers have advocated for the adoption of a copolymerization modification technique. This approach aims to imbue the gelling agent with specialized properties or intelligent regulatory capabilities, thereby surmounting the inherent limitations associated with conventional formulations. The integration of tough gel material with thermally stable rigid polymer chain units offers a promising avenue for fabricating microspherical plugging agents endowed with temperature-sensitive gels. This innovation enhances the temperature-controlled functionality of the plugging agents, thereby elevating their overall performance. Compared to conventional formulations, the comprehensive attributes encompassing physical and mechanical properties, shear resistance, and thermal stability of this novel plugging-agent material exhibit significant enhancements. Consequently, plugging agents derived from functional copolymerized gel-based microspheres have garnered considerable attention owing to their customizable and modifiable structures and properties (8), precipitating intensive research and development efforts (9,10,11). Functional groups integrated into the macromolecular chain of the gel present an effective means to tailor the high-temperature strength, temperature, salt, and shear resistances of the gel. This modulation is achieved by fine-tuning the chain structure, composition, and relative molecular mass of the polymer, while preserving the intrinsic properties of the gel (12). Leveraging this approach, a diverse array of copolymer gel-based water-plugging materials with varying compositions, structures, morphologies, and sizes have been developed. This includes the synthesis of microsphere plugging agents combined with thermosensitive gels, low-temperature hydrophobic materials, inorganic nanoparticles, and organic nanoparticles. Zhu et al. (13) prepared a viscosity-enhancing water-soluble hydrophobic polymer, by copolymerization of acrylamide and other raw materials with the introduction of hydrophobic monomers. Comparative analysis with the partially hydrolyzed PAM commonly employed revealed notable enhancements in shear resistance, salt resistance, temperature resistance, aging stability, and oil repellent properties in these copolymers, which have significantly increased the oilfield recovery on the basis of the original. Feng et al. (14) synthesized a two-tailed AM hydrophobic monomer (N-phenylethyl-N-tetradecylmethacrylamide) and copolymerized it with AM, AA, and other monomers via photoinitiated polymerization, forming a two-tailed AM hydrophobic conjugated water-soluble polymer double tailed hydrophobic associating polymer (DTHAP). Through experimental investigations, the optimal polymer content was determined. The elongation of the carbon chain within the two-tailed structure facilitated enhanced hydrophobic association between DTHAP molecules, thereby influencing its performance characteristics. Using AM and methacryloyloxyethyl-N,N-dimethylpropanesulfonic acid (DMCPS) as the basic raw materials, Wang (15) synthesized three types of novel amphiphilic hydrophobically modified water-soluble copolymers via micellar polymerization and soapless emulsion polymerization of two hydrophobic monomers (methyl styrene and docosyl polyoxyethylene methacrylate). The resultant copolymers demonstrated favorable attributes including good hydrophobicity, water solubility, and surface activity. Importantly, these copolymers retained their hydrophobic characteristics even under conditions of high shear rate and elevated temperature, rendering them widely applicable in the domain of oilfield exploitation.

Although polymer-gel microsphere plugging agents for petroleum development have been researched and developed to some extent, they are structurally complex and diverse with a high degree of functionalization. Moreover, the compositions and structures of polymer-gel microsphere plugging agents are designed for different water-plugging and regulating mechanisms, so their performances differ under different environmental conditions. Establishing constitutive relationships, intelligently regulating water plugging and dissection, and ensuring reservoir adaptability represent challenging endeavors. Despite significant advancements, the mechanisms governing water plugging and dissection of gel microspheres under diverse reservoir conditions remain incompletely elucidated. Ionic liquids have emerged as a novel green medium and functional material with commendable stability and temperature resistance, garnering substantial interest from researchers. Their designation as “green” media stems from their non-generation of volatile organic compounds during utilization (11), thereby showcasing remarkable potential for supplanting conventional technologies (16). During the preparation of gel microspheres, ionic liquids can be designed to stabilize the polymerization process and meet the requirements of green chemistry (17). When used as the reaction medium, ionic liquids achieve a fast polymerization rate under mild conditions, are widely applicable, and can be recycled many times in polymer synthesis (18). As functional materials, ionic liquids acquire special physicochemical properties through functionalized regulation of their anions and cations (19). Given their remarkable stability, temperature resistance, high functionality, design flexibility, and ease of modification of PAM-based gels, ionic liquids, and polymeric ionic liquids hold great promise as copolymerization monomers in the development of functional gel materials with enhanced performance. Through molecular structure modifications and utilization of diverse chemical components and structures, functional polymer gel microsphere plugging agents with outstanding properties can be synthesized (20,21). Hu et al. (22) employed the random copolymerization method in an ionic-liquid medium to copolymerize two monomers with different solubilities, resulting in the formation of poly(AM–co-AA) ionogels characterized by high toughness and stretchability. Jiao et al. (23) developed a mechanically strong, tough and shape-deformable poly(AM–co-vinylimidazole) [poly(AM–co-Vim)] hydrogel. Additionally, The ionic-liquid gel developed by Qu et al. (24), inherits the high hydrophobicity of the ionic liquid, ensuring stability in humid environments even during long-term operation under mechanical loading.

In this work, large-size spherical ionic-liquid copolymer gel particles with a regular shape and uniform size were designed and prepared through free-radical copolymerization using microfluidic technology. The primary constituents comprised AM and AA, while the functional monomer entailed 1-vinyl-3-propanesulfonic acid imidazolium endosulfonate [PrSO3]Vim. Notably, traditional organic solvents were supplanted with hydrophobic ionic liquids in the synthesis process. The structure and morphology of the particles were comprehensively scrutinized using suitable characterization techniques. The effects of different factors on the water absorption and strength of the gel plugging agent as well as the law of change with time were explored.

2 Materials and methods

2.1 Materials

Anhydrous ethanol (C2H5OH, AR, purity ≥99%) from Tianjin Huihang Chemical Technology Co.; N-vinylimidazole (C5H6N2, AR, purity ≥99%) and 1,3-propanesulfonolactone (C3H6O3S, AR, purity ≥99%) from Shanghai Aladdin Biochemical Technology Co., AM (AR, purity ≥98%) from Tianjin Komeo Chemical Reagent Co.; AA (AR, purity ≥98%) from Shanghai McLean Biochemical Technology Co.; sodium hydroxide (NaOH, AR, purity ≥98%) from Tianjin Hengxing Chemical Reagent Manufacturing Co.; aluminum nitrate (Al(NO3)3, AR, purity ≥98%) from Shanghai Aladdin Biochemical Technology Co.; potassium persulfate (K2S2O4, AR, purity ≥98%) were purchased from Tianjin Guangfu Fine Chemical Research Institute; and tetrahydrofuran (C4H8O, AR, purity ≥99%) from Tianjin Fuyu Fine Chemical Co. (Tianjin; Shanghai, China) were obtained. Deionized water prepared in our laboratory was used in all experiments.

2.2 Methods

The structure and purity of the ionic-liquid monomer [PrSO3]Vim were analyzed by proton nuclear magnetic resonance (1HNMR) using a high-resolution nuclear magnetic resonance spectrometer (AV400MHz, Bruker Co., Germany) with D2O as the appearance deuterated reagent, standardized at 298 K. The prepared ionic-liquid [PrSO3]Vim monomers and P(AM–AA–[PrSO3]Vim) spherical gel particles were subjected to Fourier transform infrared spectroscopy (FTIR) using the potassium bromide compression method in a Fourier-exchange infrared spectrometer. The microscopic morphology of the P(AM–AA–[PrSO3]Vim) spherical gel particles was observed using scanning electron microscopy (SEM) (JSM-5600F, Gansu, China). Prior to SEM analysis, the surfaces and cross-sections of the gel particles were sprayed with gold to produce a stronger signal and improve the resolution of the SEM.

2.3 Experimental process

2.3.1 Preparation of the P(AM–AA–[PrSO3]Vim) gel blocking particles

Preparation of the P(AM–AA–[PrSO3]Vim) gel blocking particles.

  1. Synthesis of the functional ionic liquid: 1-vinyl-3-propylsulfonic acid imidazolium inner salt ([PrSO3]Vim).

The ionic liquids were synthesized with reference to a previous study (25). The solvent (tetrahydrofuran) and equimolar amounts of 1-vinylimidazole (Vim) and 1,3-propanesulfonate (PrSO3) were added to a nitrogen-protected three-necked flask with stirring and reacted for 24 h at 45℃ in a water bath, obtaining a white solid in the liquid. The product was pumped, filtered, and repeatedly washed with petroleum ether three times. After rotary evaporation and vacuum-drying for 24 h, a white solid powder was obtained. The powder was sealed and preserved in a sealed bottle in the dark. The preparative reaction is shown in Figure 1.

  1. Preparation of P(AM–AA–[PrSO3]Vim) spherical gel-plugging particles

Figure 1 Preparation route of 1-vinyl-3-propyl sulfonate imidazole from 1-vinylimidazole and 1,3-propanesulfonate.
Figure 1

Preparation route of 1-vinyl-3-propyl sulfonate imidazole from 1-vinylimidazole and 1,3-propanesulfonate.

Figure 2 Preparation of the (AM–AA–[PrSO3]Vim) spherical gel particles.
Figure 2

Preparation of the (AM–AA–[PrSO3]Vim) spherical gel particles.

In an ice water bath, a specified amount of AA and a small amount of distilled water were added to a beaker and stirred. A certain amount of sodium hydroxide was then slowly added to neutralize the system to 60%. After adding AM to the same amount as AA, the system concentration, i.e., the ratio of the solute to the whole system, was adjusted to 30% with distilled water. The prepared functional ionic-liquid 1-vinyl-3-propylsulfonic acid imidazolium inner salt was added at the levels shown in Table 1, followed by 1% of the cross-linker Al(NO3)3 and 1% of the initiator K2S2O4. The system was ultrasonicated to ensure an even reaction. The configured solution was then added dropwise into a centrifuge tube containing 1-butyl-3-dodecylimidazole hexafluorophosphate ([C12bim]PF6, a hydrophobic ionic liquid). The centrifuge tube was placed in a thermostatic oil bath at 90℃ for 5–8 min, allowing the reaction to proceed. The product was extracted from the tube and washed with anhydrous ethanol for several times, ventilated and dried for 3 h at room temperature. Finally, the air-dried product was placed in a constant-temperature drying oven, dried to constant weight, and sealed in a bag until required for analysis. The reaction flow is shown in Figure 2.

Table 1

Molar ratios of 1-vinyl-3-propyl sulfonate imidazole internal salt to (AA + AM)

Number 1 2 3 4 5
n([PrSO3]Vim): n(AA + AM) 4% 8% 12% 16% 20%

2.4 Testing and performance characterization

2.4.1 Density determination

To determine the apparent density, the diameter and weight of each sample in a group of randomly selected sample particles were measured and averaged to give the final diameter D (mm) and weight M (g). The apparent density ρ (g·mL−1) of the particles was then calculated as follows:

(1) ρ 1 = 6 M π D − 3

To determine the bulk density, the total mass of a number of randomly selected sample particles was recorded as m (g). A 10 mL measuring cylinder was filled with tetrahydrofuran and its volume was recorded as V 1 (mL). After placing the selected gel particles into the tetrahydrofuran, the new volume was recorded as V 2 (mL). The volume of the gel particles was computed as the volume difference ΔV = V 2 − V 1 and the bulk density ρ (g·mL−1) was calculated as follows:

(2) ρ 0 = m Δ V

2.4.2 Determination of water absorption

A selected number of gel particles was weighed on an electronic balance. The particles with a collective initial weight of m 0 (g) were loaded into a filter bag with a certain number of meshed particles. The bag was sealed at the mouth and its weight was recorded as m 1 (g). The bag was immersed in a water bath containing distilled water and brine at 20°C. At specified intervals, the water on the bag surface was controlled and the bag was weighed. Its weight was recorded as m 2 (g). Measurements were terminated at absorption–expansion equilibrium. Applying the same procedure, data were collected at 30°C, 40°C, 50°C, 60°C, and 70°C. The water absorption Q was then calculated as reported by Anal and Stevens (26).

(3) Q = m 2 − m 1 m 0

2.4.3 Strength measurements

The strengths of the gel particles after water absorption and expansion were determined using a strength tester constructed in our laboratory. Gel particles prepared at different concentrations were placed in distilled water at 20℃, 30℃, 40℃, 50℃, 60℃, or 70℃, removed after soaking for 4 h, and placed in the measuring instrument. The gel was touched with the lower end of the pressure bar and weights were added to the weight tray until the gel broke. The strength S (kPa) of the gel particles was computed as follows (27):

(4) S = G 1 + G 2 − f A

where G 1 is the gravity of the weights; G 2 is the total gravity of the weight table, connecting rod, and pressure rod, calculated as G 2 = m 0 g , where m 0 is the total initial mass (g), (mass of the weight table, connecting rod, and pressure rod); A is the cross-sectional area of the pressure rod (m2); g is the gravitational acceleration (9.8 m·s−2); and f is the friction force (N). The contact forces between the pressure rod and the surfaces and inner wall of the casing are negligible when the surfaces are sufficiently smooth.

3 Results

3.1 NMR analysis of the 1-vinyl-3-propylsulfonic acid imidazolium inner salt [PrSO3]Vim

Figure 3 illustrates the 1H NMR hydrogen spectrum of [PrSO3]Vim. The peak at δ 9.06 (Figure 3a) corresponds to the hydrogen in the –N–CH═N– group of the imidazolium ring, while the peaks at δ 7.59–7.76 (Figure 3b and c) represent the –CH═CH– groups of the imidazolium ring. Additionally, the peak at δ 7.10 (Figure 3d) is attributed to the direct attachment of the vinyl imidazolium ring to H (CH2═CH–N). Peaks at δ 5.40 and δ 5.76 (Figure 3e) signify the vinyl-terminated H (CH2═CH), while the δ 4.79 peak corresponds to the deuterated reagent D2O. Furthermore, the peak at δ 4.36 (Figure 3f) is ascribed to the characteristic peaks of methylene H (–CH2–) directly linked to the imidazole ring. Peaks at δ 2.91 and δ 2.31 represent the characteristic peaks of methylene H (–CH2–) at positions g and h in Figure 3, respectively, with the latter methylene being linked to the sulfonic acid moiety. The polymer structure determined by the NM mapping aligns with that of [PrSO3]Vim, thus corroborating its consistency.

Figure 3 Hydrogen nuclear magnetic spectrum of [PrSO3]Vim.
Figure 3

Hydrogen nuclear magnetic spectrum of [PrSO3]Vim.

3.2 FTIR characterization of the [PrSO3]Vim and poly(AM–AA–[PrSO3]Vim) gel particles

Figure 4 displays the FTIR spectra of the P(AM–AA–[PrSO3]Vim) copolymerized gel temporary blocking particles alongside the [PrSO3]Vim ionic-liquid monomer. In the FTIR spectrum of [PrSO3]Vim (black spectrum in Figure 4), the characteristic absorption band of O–H at 3,446 cm−1 indicates that the monomer was not completely purged of moisture; alternatively, the monomer absorbed moisture when exposed to air. The absorption peak at 3,137 cm−1 corresponds to C–H stretching vibrations on the imidazole ring, while the peak at 3,087 cm−1 represents the characteristic absorption band of the methylene group on the vinyl group. Peaks at 2,933 and 2,867 cm−1 denote the antisymmetric and symmetric stretching vibrations of methylene (–CH2–), respectively. The peak at 1,645 cm−1 is attributed to C═C vibrations, while peaks at 1,573 and 1,455 cm−1 arise from vibrations of the imidazole ring skeleton. Additionally, the peak at 1,230 cm−1 corresponds to stretching vibrations of the imidazole ring. The –SO3– stretching vibrations manifest at 1,174 and 1,054 cm−1. The combined analysis of the 1H NMR spectrum and the FTIR spectrum conclusively verifies the structure of the ionic-liquid [PrSO3]Vim monomer. Meanwhile, the FTIR spectrum of the P(AM–AA–[PrSO3]Vim) gel particles presents the characteristic band of free NH2 at 3,423 cm−1, the peak of –NH2 binding vibrations at 3,234 cm−1, the peaks of methylene stretching vibrations at 2,925 and 2,856 cm−1 and the characteristic band of the carbonyl group C═O at 1,677 cm−1. The peaks at 1,569 and 1,448 cm−1 belong to stretching vibrations of the imidazole ring. The peak at 1,677 cm−1 is the characteristic band of carbonyl C═O, the peaks at 1,569 and 1,448 cm−1correspond to the vibration band of the imidazole ring skeleton and the absorption peaks at 1,187 and 1,037 cm−1 are attributed to stretching vibrations of the imidazole ring and SO 3 − , respectively. These characterization results unequivocally demonstrate the copolymerization of [PrSO3]Vim with the AM and AA systems, resulting in the formation of P(AM–AA–[PrSO3]Vim) gel particles.

Figure 4 Infrared spectra of gel granules of the [PrSO3]Vim copolymer (black) and P(AM–AA–[PrSO3]Vim) (red). (a) P(AM-AA-[PrSO3]Vim) and (b) [PrSO3]Vim copolymer.
Figure 4

Infrared spectra of gel granules of the [PrSO3]Vim copolymer (black) and P(AM–AA–[PrSO3]Vim) (red). (a) P(AM-AA-[PrSO3]Vim) and (b) [PrSO3]Vim copolymer.

3.3 SEM characterization of the P(AM–AA–[PrSO3]Vim) gel particles

Panels (a) and (b) of Figure 5 depict surface and cross-sectional SEM images, respectively, of the P(AM–AA–[PrSO3]Vim) gel particles. The prepared gel particles exhibit high sphericity and possess smooth surfaces, characterized by a relatively uniform size distribution ranging from 2 to 3 mm. The internal morphology of the polymer-gel particles appears rough, featuring a relatively dense structure formed by the linkage of hydrophobic chains into a three-dimensional network with a regularly distributed pore structure. This internal configuration imparts the polymer with a high water absorption capacity and exceptional compressive strength.

Figure 5 SEM images of the P(AM–AA–[PrSO3]Vim) gel microspheres. (a) and (b) The surface and cross-sectional images, respectively, of the P(AM–AA–[PrSO3]Vim) gel particles.
Figure 5

SEM images of the P(AM–AA–[PrSO3]Vim) gel microspheres. (a) and (b) The surface and cross-sectional images, respectively, of the P(AM–AA–[PrSO3]Vim) gel particles.

3.4 Density variation in the P(AM–AA–[PrSO3]Vim) gel particles

Figure 6 plots the densities of the P(AM–AA–[PrSO3]Vim) gel particles as a function of [PrSO3]Vim content. Remarkably, the density of the P(AM–AA–[PrSO3]Vim) gel particles exhibits an increasing trend with rising [PrSO3]Vim content. Notably, the apparent density is observed to be smaller than the bulk density, primarily due to the non-spherical shape of the gel particles prepared using the titration gelation method, contrary to the assumption of complete sphericity in theoretical derivations. The ratio of apparent density to bulk density consistently exceeded 0.85 and reached a maximum of 0.94, indicating that the prepared polymer-gel particles were regularly shaped and uniformly sized. Consequently, it can be inferred that the polymer-gel particles assume a spherical and more uniform shape in the ionic-liquid medium compared to conventional media.

Figure 6 Relationships between P(AM–AA–[PrSO3]Vim) gel-particle densities and [PrSO3]Vim content. The higher and lower black lines plot the bulk and apparent densities, respectively, and the red line plots the ratio of apparent density to bulk density.
Figure 6

Relationships between P(AM–AA–[PrSO3]Vim) gel-particle densities and [PrSO3]Vim content. The higher and lower black lines plot the bulk and apparent densities, respectively, and the red line plots the ratio of apparent density to bulk density.

3.5 Effect of different factors on water absorption capacity of the P(AM–AA–[PrSO3]Vim) gel particles

3.5.1 Effect of [PrSO3]Vim dosage on water absorption capacity of the P(AM–AA–[PrSO3]Vim) gel particles

As depicted in Figure 7, the water absorption of the polymer gel particles exhibits a trend of initial increase followed by a decrease with the augmentation of [PrSO3]Vim addition. When the [PrSO3]Vim addition is below 12%, the water absorption of the polymer gel plugging agent particles demonstrates a rapid increase across different temperature ranges. Particularly, at a [PrSO3]Vim addition of 12%, a significantly elevated water absorption rate is observed across all temperature ranges. When the content of [PrSO3]Vim is low, it is positively correlated with the water absorption rate of the gel particles, on the one hand, the reason is that the change in the content of [PrSO3]Vim makes the polymerization degree of the polymer gel particles change, and the molecular chains with a certain cross-linking density form the structure with spatial geometry through spatial entanglement, so as to improve the water retention capacity of the gel particles; On the other hand, the synergistic effect of the nonionic group amide-CONH2 and the ionic group sulfonic acid group-SO3- enhanced the hydrophilicity of the gel particles, which lead to an increase in water absorption. It can also be seen from the figure that the water absorption of P(AM-AA-[PrSO3]Vim) polymer gel particles initially increases and then decreases with the rise in temperature, exhibiting optimal water absorption at 40°C, reaching up to 137 g·g−1. At lower temperatures, the bonding effect of the hydrophobic groups is relatively weak, and the movement of the molecular chains is sluggish, resulting in lower water absorption of the polymer gel plugging agent particles. With increasing temperature, the molecular chains within the three-dimensional network structure of the polymer gel particles gradually elongate, maximizing the bonding effect of the hydrophobic groups and consequently leading to higher water absorption. However, as the temperature surpasses 40°C, the water absorption rate diminishes. This decline can be attributed to the hydrolyzable nature of the materials used in the preparation of the polymer gel particles. With elevated temperatures, the hydrolysis rate accelerates, thereby reducing the water retention capacity and subsequently lowering the water absorption rate. Despite the decrease in water retention capacity, the polymer gel particles still demonstrate certain levels of water absorption and retention capabilities.

Figure 7 Relationship between water absorption and [PrSO3]Vim dosage in the polymer-gel particles at different temperatures.
Figure 7

Relationship between water absorption and [PrSO3]Vim dosage in the polymer-gel particles at different temperatures.

3.5.2 Effect of cross-linker dosage on water absorption of the P(AM–AA–[PrSO3]Vim) gel particles

Figure 8 illustrates the correlation between water absorption capacity and cross-linker amount in the P(AM–AA–[PrSO3]Vim) gel particles containing 12% [PrSO3]Vim at various temperatures. Across each temperature, the water absorption capacity of the P(AM–AA–[PrSO3]Vim) particles exhibited a tendency to first increase and then decrease with rising cross-linker content. The swelling and quantity of absorbed water reached their peak at a cross-linker content of 1.5%.

Figure 8 Relationship between water absorption and cross-linker amount in the P(AM–AA–[PrSO3]Vim) polymer-gel particles at different temperatures.
Figure 8

Relationship between water absorption and cross-linker amount in the P(AM–AA–[PrSO3]Vim) polymer-gel particles at different temperatures.

When the dosage is below 1.25%, the water absorption of the polymer gel plugging agent increases, albeit at lower overall levels. This phenomenon arises because it becomes more challenging for the polymer to form an ideal three-dimensional entangled mesh structure. With relatively high water solubility, the water absorption decreases, and the strength of the gel particles is significantly impacted. Upon absorbing water, the gel particles do not attain an elastic gel state but instead transform into non-strength dilute thick colloids. Conversely, when the cross-linking amount exceeds 1.5%, the cross-linking density becomes excessively large, resulting in the contraction of space within the network. Consequently, the structure becomes denser, leading to a reduction in its water-absorbing capacity.

3.5.3 Analysis of particle strength in the P(AA–AM–[PrSO3]Vim) gels

Figure 9 shows the relationship between the [PrSO3]Vim additions and the strength of the gel particles at 40℃. With increasing [PrSO3]Vim content, the strength of gel particles first increased and then decreased, and the strength was the best when the [PrSO3]Vim addition was 4%. This phenomenon arises because the addition of an appropriate amount of the third monomer [PrSO3]Vim improves the strength of the gel particles by the ion–dipole, dipole–dipole interactions and interchain hydrogen bonding in the structure of the polymer-gel particles. The inherent strength of the ionic liquid itself contributes to improving the product’s strength, as the functional ionic liquid containing an imidazole ring inherently possesses robust mechanical properties. Consequently, the addition of functional ionic liquid also bolsters the stability of the polymer gel particles. However, as the amount of [PrSO3]Vim increases, the sulfonic acid group content within the polymer gel particles rises, promoting the hydrolysis of the gel particles and subsequently increasing the solubility of the temporary plugging agent. This results in a corresponding decrease in compressive strength. Thus, the addition of [PrSO3]Vim in appropriate amounts can enhance the strength of polymer-gel plugging agent particles.

Figure 9 Relationship between gel-particle strength and [PrSO3]Vim dosage.
Figure 9

Relationship between gel-particle strength and [PrSO3]Vim dosage.

4 Discussion

1-Vinyl-3-propylsulfonic acid imidazolium inner salt ([PrSO3]Vim) functional ionic liquids were synthesized using a one-step method. Subsequently, Ionic liquid–AM-based copolymerized gel P(AM–AA–[PrSO3]Vim) plugging particles were then prepared via free-radical polymerization using microfluidic technology and the titration gel method. Varied concentrations of [PrSO3] Vim functional ionic liquids were used as auxiliary reinforcement materials. The water absorption capacity of the P(AM–AA–[PrSO3]Vim) copolymerized gel particles was related to the [PrSO3]Vim dosage and cross-linker concentration at different temperatures. When the [PrSO3]Vim dosage was 12% and the cross-linker concentration was 1.5%, the water absorption capacity was maximized at 40℃, reaching 163 g·g−1. From the relationship between the strength and [PrSO3]Vim content in the copolymerized gel particles at 40°C, a [PrSO3]Vim content of 4% was found to optimize the strength.

5 Conclusion

In summary, P(AM–AA–[PrSO3]Vim) copolymerized gel-plugging particles with high compressive strength, excellent stability, and intelligently controllable gel-plugging performance were designed and developed through microfluidic technology and the titration gel method, employing functional ionic liquids as the preparation medium. This high-performance plugging-agent, oil-repellant material is well-suited for enhancing oil well fracturing processes. The behavior and water-plugging performance of the spherical gel-plugging particles were thoroughly investigated across various transportation stages in a simulated environment. Moreover, the chemical and physical roles of the spherical gel-plugging particles were meticulously examined in a typical water-plugging environment. This study provides experimental data and a theoretical basis for the application of functional spherical gel-plugging particles in current oilfield environments.

  1. Funding information: The authors are grateful to the National Natural Science Foundation of China (Grant No. 52363010) and the Science Foundation of State Key Laboratory of Advanced Processing and Recycling of Non-ferrous Metals.

  2. Author contributions: All authors contributed to the study conception and design. Methodology, formal analysis, investigation, and writing-original draft preparation: Mei-Ju Zhang. Review, supervision, and funding acquisition: Ding-Jun Zhang. Data collection and material preparation: Zhan-Dong Luo and Sheng-Xiang Zhang. All authors commented on previous versions of the manuscript. All authors read and approved the final manuscript.

  3. Conflict of interest: No conflict of interest.

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Received: 2024-01-28
Revised: 2024-06-05
Accepted: 2024-07-11
Published Online: 2024-09-18

© 2024 the author(s), published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

Artikel in diesem Heft

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  3. Highly stretchable, durable, and reversibly thermochromic wrapped yarns induced by Joule heating: With an emphasis on parametric study of elastane drafts
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https://doi.org/10.1515/epoly-2024-0016
Schlagwörter für diesen Artikel
functional ionic liquids; ionic liquids polymer; copolymerization reaction; green chemistry
Creative Commons
BY 4.0

Artikel in diesem Heft

  1. Research Articles
  2. Flame-retardant thermoelectric responsive coating based on poly(3,4-ethylenedioxythiphene) modified metal–organic frameworks
  3. Highly stretchable, durable, and reversibly thermochromic wrapped yarns induced by Joule heating: With an emphasis on parametric study of elastane drafts
  4. Molecular dynamics simulation and experimental study on the mechanical properties of PET nanocomposites filled with CaCO3, SiO2, and POE-g-GMA
  5. Multifunctional hydrogel based on silk fibroin/thermosensitive polymers supporting implant biomaterials in osteomyelitis
  6. Marine antifouling coating based on fluorescent-modified poly(ethylene-co-tetrafluoroethylene) resin
  7. Preparation and application of profiled luminescent polyester fiber with reversible photochromism materials
  8. Determination of pesticide residue in soil samples by molecularly imprinted solid-phase extraction method
  9. The die swell eliminating mechanism of hot air assisted 3D printing of GF/PP and its influence on the product performance
  10. Rheological behavior of particle-filled polymer suspensions and its influence on surface structure of the coated electrodes
  11. The effects of property variation on the dripping behaviour of polymers during UL94 test simulated by particle finite element method
  12. Experimental evaluation on compression-after-impact behavior of perforated sandwich panel comprised of foam core and glass fiber reinforced epoxy hybrid facesheets
  13. Synthesis, characterization and evaluation of a pH-responsive molecular imprinted polymer for Matrine as an intelligent drug delivery system
  14. Twist-related parametric optimization of Joule heating-triggered highly stretchable thermochromic wrapped yarns using technique for order preference by similarity to ideal solution
  15. Comparative analysis of flow factors and crystallinity in conventional extrusion and gas-assisted extrusion
  16. Simulation approach to study kinetic heterogeneity of gadolinium catalytic system in the 1,4-cis-polyisoprene production
  17. Properties of kenaf fiber-reinforced polyamide 6 composites
  18. Cellulose acetate filter rods tuned by surface engineering modification for typical smoke components adsorption
  19. A blue fluorescent waterborne polyurethane-based Zn(ii) complex with antibacterial activity
  20. Experimental investigation on damage mechanism of GFRP laminates embedded with/without steel wire mesh under low-velocity-impact and post-impact tensile loading
  21. Preparation and application research of composites with low vacuum outgassing and excellent electromagnetic sealing performance
  22. Assessing the recycling potential of thermosetting polymer waste in high-density polyethylene composites for safety helmet applications
  23. Mesoscale mechanics investigation of multi-component solid propellant systems
  24. Preparation of HTV silicone rubber with hydrophobic–uvioresistant composite coating and the aging research
  25. Experimental investigation on tensile behavior of CFRP bolted joints subjected to hydrothermal aging
  26. Structure and transition behavior of crosslinked poly(2-(2-methoxyethoxy) ethylmethacrylate-co-(ethyleneglycol) methacrylate) gel film on cellulosic-based flat substrate
  27. Mechanical properties and thermal stability of high-temperature (cooking temperature)-resistant PP/HDPE/POE composites
  28. Preparation of itaconic acid-modified epoxy resins and comparative study on the properties of it and epoxy acrylates
  29. Synthesis and properties of novel degradable polyglycolide-based polyurethanes
  30. Fatigue life prediction method of carbon fiber-reinforced composites
  31. Thermal, morphological, and structural characterization of starch-based bio-polymers for melt spinnability
  32. Robust biaxially stretchable polylactic acid films based on the highly oriented chain network and “nano-walls” containing zinc phenylphosphonate and calcium sulfate whisker: Superior mechanical, barrier, and optical properties
  33. ARGET ATRP of styrene with low catalyst usage in bio-based solvent γ-valerolactone
  34. New PMMA-InP/ZnS nanohybrid coatings for improving the performance of c-Si photovoltaic cells
  35. Impacts of the calcinated clay on structure and gamma-ray shielding capacity of epoxy-based composites
  36. Preparation of cardanol-based curing agent for underwater drainage pipeline repairs
  37. Preparation of lightweight PBS foams with high ductility and impact toughness by foam injection molding
  38. Gamma-ray shielding investigation of nano- and microstructures of SnO on polyester resin composites: Experimental and theoretical study
  39. Experimental study on impact and flexural behaviors of CFRP/aluminum-honeycomb sandwich panel
  40. Normal-hexane treatment on PET-based waste fiber depolymerization process
  41. Effect of tannic acid chelating treatment on thermo-oxidative aging property of natural rubber
  42. Design, synthesis, and characterization of novel copolymer gel particles for water-plugging applications
  43. Influence of 1,1′-Azobis(cyclohexanezonitrile) on the thermo-oxidative aging performance of diolefin elastomers
  44. Characteristics of cellulose nanofibril films prepared by liquid- and gas-phase esterification processes
  45. Investigation on the biaxial stretching deformation mechanism of PA6 film based on finite element method
  46. Simultaneous effects of temperature and backbone length on static and dynamic properties of high-density polyethylene-1-butene copolymer melt: Equilibrium molecular dynamics approach
  47. Research on microscopic structure–activity relationship of AP particle–matrix interface in HTPB propellant
  48. Three-layered films enable efficient passive radiation cooling of buildings
  49. Electrospun nanofibers membranes of La(OH)3/PAN as a versatile adsorbent for fluoride remediation: Performance and mechanisms
  50. Preparation and characterization of biodegradable polyester fibers enhanced with antibacterial and antiviral organic composites
  51. Preparation of hydrophobic silicone rubber composite insulators and the research of anti-aging performance
  52. Surface modification of sepiolite and its application in one-component silicone potting adhesive
  53. Study on hydrophobicity and aging characteristics of epoxy resin modified with nano-MgO
  54. Optimization of baffle’s height in an asymmetric twin-screw extruder using the response surface model
  55. Effect of surface treatment of nickel-coated graphite on conductive rubber
  56. Experimental investigation on low-velocity impact and compression after impact behaviors of GFRP laminates with steel mesh reinforced
  57. Development and characterization of acetylated and acetylated surface-modified tapioca starches as a carrier material for linalool
  58. Investigation of the compaction density of electromagnetic moulding of poly(ether-ketone-ketone) polymer powder
  59. Experimental investigation on low-velocity-impact and post-impact-tension behaviors of GFRP T-joints after hydrothermal aging
  60. The repeated low-velocity impact response and damage accumulation of shape memory alloy hybrid composite laminates
  61. Exploring a new method for high-performance TPSiV preparation through innovative Si–H/Pt curing system in VSR/TPU blends
  62. Large-scale production of highly responsive, stretchable, and conductive wrapped yarns for wearable strain sensors
  63. Preparation of natural raw rubber and silica/NR composites with low generation heat through aqueous silane flocculation
  64. Molecular dynamics simulation of the interaction between polybutylene terephthalate and A3 during thermal-oxidative aging
  65. Crashworthiness of GFRP/aluminum hybrid square tubes under quasi-static compression and single/repeated impact
  66. Review Articles
  67. Recent advancements in multinuclear early transition metal catalysts for olefin polymerization through cooperative effects
  68. Impact of ionic liquids on the thermal properties of polymer composites
  69. Recent progress in properties and application of antibacterial food packaging materials based on polyvinyl alcohol
  70. Additive manufacturing (3D printing) technologies for fiber-reinforced polymer composite materials: A review on fabrication methods and process parameters
  71. Rapid Communication
  72. Design, synthesis, characterization, and adsorption capacities of novel superabsorbent polymers derived from poly (potato starch xanthate-graft-acrylamide)
  73. Special Issue: Biodegradable and bio-based polymers: Green approaches (Guest Editors: Kumaran Subramanian, A. Wilson Santhosh Kumar, and Venkatajothi Ramarao)
  74. Development of smart core–shell nanoparticles-based sensors for diagnostics of salivary alpha-amylase in biomedical and forensics
  75. Thermoplastic-polymer matrix composite of banana/betel nut husk fiber reinforcement: Physico-mechanical properties evaluation
  76. Special Issue: Electrospun Functional Materials
  77. Electrospun polyacrylonitrile/regenerated cellulose/citral nanofibers as active food packagings
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