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Characterization study of polyAMPS@BMA core-shell particles using two types of RAFT agents

Published Online: 25 Jul 2021
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Received: 19 May 2021
Accepted: 24 Jun 2021
Journal Details
License
Format
Journal
First Published
16 Apr 2011
Publication timeframe
4 times per year
Languages
English
Abstract

The study and application of reversible addition-fragmentation chain transfer (RAFT) polymerization have been widely reported in the literature because of its high compatibility with numerous monomers, reaction conditions, and low polydispersity index. The effect of RAFT agents on the characteristics of the final product is greatly needed to be explored. Our present study aimed to compare the influence of two different types of RAFT agents on the characteristics of the water-soluble polymer (2-acrylamido-2-methylpropane sulfonic acid) (polyAMPS) and their polyAMPS@butyl methacrylate (BMA) core-shell particles. Different analytical techniques including scanning electron microscopy (SEM), fourier transform infrared spectroscopy (FTIR), energy dispersive X-ray analysis (EDX), X-ray diffraction (XRD), and thermogravimetric analysis (TGA) were used to ascertain the final morphological, structural, and thermal properties of the resultant products. It was found that RAFT agents have shown a clear influence on the final properties of the resultant polyAMPS and their core-shell particles such as particle size, shape, size distribution, and thermal behavior. This study confirms that RAFT agents can control the final properties of the polymers and their core-shell particles.

Keywords

Introduction

Polymers became the center of research over the past few decades due to their good adaptability [1, 2] and various potential applications in the field of medical [3, 4], pharmaceutical [5], and other industrial applications [6, 7]. The prerequisite for complete control over the application of polymers is the “polymerization process”. The advantages and shortcomings of polymerization process are dependent on its low versatility or compatibility over different monomer, solvent system, provided conditions and suitable initiators [8]. One of the most prominent polymerizations include controlled/living radical polymerization (CLRP). Among all other CLRP, the most advance type of polymerization which uses thiocarbonylthio functionality, provides relatively high versatility over a provided condition (solvent, temperature, pH and initiator), functional and nonfunctional monomers to yield desire material with complex architectures, narrow molecular weight distributions, and pre-determined molecular weights [9]. This thiocarbonylthio functionality is provided by reversible addition-fragmentation chain-transfer (RAFT) agents, which leads to RAFT polymerization. Since the invention of RAFT polymerization, numerous RAFT agents have been synthesized and reported [10].

RAFT polymerizations have been used in the synthesis of various polymeric architectures, such as star [11], brush [11], linear [12], dendrimer [13], core-shell [14], and graft [15], along with different conditions, namely, solution, suspension, emulsion, and miniemulsion polymerizations [16]. Dispersity is one of the prominent parameters that affects the properties of polymers. Control over dispersity can be attained by mixing two RAFT agents with adequately dissimilar chain-transfer behaviors in different ratios, affording polymers with monomodal molecular weight distributions over a broad dispersity range [17]. Henkel and Vana [18] studied the effect of RAFT agents on the mechanical and the microstructure behavior of poly(butyl acrylate). For this purpose, a photoinitiated polymerization of 1,4-butanediol diacrylate and butyl acrylate was conducted in the absence and presence of RAFT agents. It was found that RAFT-based polymers have lower Young's moduli and high swelling degree. Moreover, kinetic differential scanning calorimetry studies illustrated that the gel point was retarded with enlarging the content of RAFT agent [18]. Masuda and Takai [19] studied the effect of RAFT agent content on the microstructure and properties of poly(N-isopropylacrylamide) (PNIPAAm) gels. A millimeter-sized cylinder was synthesized from PNIPAAm gels. Swelling and deswelling behaviors were studied, and we found that a cylinder with high “RAFT agent content” showed fast deswelling properties [19]. The various multi-arm RAFT agents have been used in stereolithographic 3D printing. Further, it was widely found that changing the functionality and content of RAFT agents result in obtaining control over material mechanical behavior in a broad span [20]. Application of RAFT polymerization instead of free radical polymerization produced major variations in the mechanical, uptake behaviors and thermal properties, which seem to reflect the improvement in polymer uniformity and mobility frequently related with controlled polymerization [21].

The application and properties of core-shell nanomaterials can be promisingly controlled by the right selection of shell or core materials according to the environment/condition and applications. A vast study of core-shell material “as sensing” device have been reported, i.e., as optical sensors, gas adsorptive sensors, electrochemical sensors, and wearable sensing devices. These devices have various potential uses in food analysis and biological, industrial, environmental, and clinical applications. Moreover, numerous synthetic approaches with various prominent properties of core-shell materials, such as high ion transport properties, high conductivities, and high surface area have been studied. [22]

Although the synthesis of RAFT agents and their use in the preparation has already been reported [23, 24], to our knowledge, their effect on the final characteristics of the prepared water-soluble polymer (2-acrylamido-2-methylpropane sulfonic acid) (polyAMPS) and their core-shell particles has not been reported. Hence, considering various advantages of RAFT polymerization, this effort was made to determine their role in controlling the thermal stability, particle size distribution, crystallinity, and average particle size of the resultant core-shell particles with polyAMPS as a shell and butyl methacrylate (BMA) as a core.

Experimental section
Materials

Potassium persulfate, sodium hydride, magnesium turnings, and carbon disulfide were purchased from Daejung, Korea. 4-vinylbenzyl chloride, 4,4′-azobis(4-cyanovaleric acid) (ABCA), dimethylformamide (DMF), BMA, 2-acrylamido-2-methylpropane sulfonic acid (AMPS), iodine, magnesium sulfate, potassium persulfate (K2S2O8), n-hexane, diethyl ether, bromobenzene, dimethyl sulfoxide, petroleum ether, and tetra hydrofuran were purchased from Sigma-Aldrich. Pyrroles and silica gel were the products of Unichem, USA.

Instruments used

The FTIR analysis was done via Thermo Fisher Scientific model NICOLET iS5. Scanning electron microscopic and energy dispersive X-ray analyses were done via field-emission scanning electron microscopy (SEM), JEOL Japan, model JSM5910, with an acceleration voltage of 30 KV. X-ray diffraction (XRD) pattern was recorded via an X-ray diffractometer (model JDX-3532), JEOL Japan, by using Ni-filtered Cu Kα radiation and a wavelength of 1.5418 Å. Thermogravimetric analysis was done with TGA instrument from PerkinElmer (USA), model TGA 4000.

Preparation of RAFT agents

In the study, two different RAFT agents 4-vinylbenzyl pyrrolecarbodithioate and 4-vinylbenzyl dithiobenzoate (4VP and 4VD, respectively) were separately prepared using the reported protocols with some modifications [24]. Briefly, for the preparation of 4VP, 6.02 g of NaH was mixed in 160.00 ml of DMF, followed by stepwise addition of 10.02 g/20 ml of pyrrole, 9.01 ml/20 ml CS2, and 22.2/20 ml of 4-vinylbenzyl chloride, which were all dissolved in DMF. The mixture was stirred for 12 h. For the isolation of 4VP, the resultant product was washed with diethyl ether and distilled water (1:1), followed by extraction via column chromatography, in which petroleum ether was used as a mobile phase. The petroleum ether was separated through vacuum distillation, and the final product, 4VP, was stored at −18 °C in an inert environment. For the synthesis of 4VD, 3.301 g of magnesium turning was dissolved in 14 ml/40 ml bromobenzene (in tetrahydrofuran), and to initiate this reaction, 0.1 g of iodine was added. CS2 [7.91 ml/5 mL (in tetrahydrofuran)] and 4-vinylbenzyl chloride [7.19 mL/5 ml (in tetrahydrofuran)] were added in a stepwise manner after stirring for 12 h. The same isolation process was followed for 4VD. Structures of these two RAFT agents are given in Figure 1.

Fig. 1

Structures of the as-prepared RAFT agents. RAFT, reversible addition-fragmentation chain-transfer.

Preparation of polyAMPSi and polyAMPSii

For the preparation of water-soluble polymer poly(2-acrylamido-2-methylpropane sulfonic acid) (polyAMPSi), the previously reported method was adopted with certain minor modifications [23]. Briefly, for the synthesis of polyAMPSi, a known amount of AMPS monomer, 4VP (25:1), and ABCA were added to 25 ml of dimethyl sulfoxide under an oxygen-free environment. The reacting flask was deoxygenated with nitrogen gas purging and vacuum pump followed by fitting it to water bath for 12 h at 333 K. After 12 h at 333 K, a brownish color polyAMPSi was prepared which was stored at 268 K in an inert environment. The same protocol was used for polyAMPSii but 4VP was replaced with 4VD.

Preparation of core-shell particles

For the preparation of CSi, 25 ml of BMA was slowly added to 1 g/300 ml of polyAMPSi solution in distilled water, followed by addition of potassium persulfate (K2S2O8) solution (1 g/15 ml). The whole setup was oxygen-free; this was ensured through the usage of an overhead condenser and magnetic stirrer, which was later fitted in a water bath for 12 h at 333 K. The same protocol was used for preparation of CSii but polyAMPSi was replaced with polyAMPSii.

Characterizations

FTIR analysis was carried out to confirm the presence of various functional groups. TGA analysis was used to study the control of RAFT agents over thermal properties (stability). XRD was done to determine the effect on the semicrystalline nature of the obtained CS particles. The SEM study was used to study the morphology and influence of RAFT agents on the particle size of the obtained CS particles.

Results and discussion
FTIR analysis of polyAMPS and core-shell particles

The FTIR analysis given in Figure 2 reveals the successful preparation of polyAMPSi and polyAMPSii, which is confirmed by the presence of various characteristic peaks, such as asymmetric and symmetric vibrations of −SO2 at 1,031 cm−1 and 1,210 cm−1, N-H and C=O vibrations at 1,538 cm−1 and 1,665 cm−1, and −CH3 and −CH2 asymmetric and symmetric stretching at 2,996 and 2,913 cm−1, respectively. These peaks are found in the structure of polyAMPS, and the data are in agreement with the literature [25, 26].

Fig. 2

FTIR spectra of the as-prepared polyAMPSi and polyAMPSii. polyAMPS, poly(2-acrylamido-2-methylpropane sulfonic acid).

The CSi and CSii were synthesized with the application of as-prepared polyAMPSi and polyAMPSii. FTIR was carried out to evaluate their structure, and different characteristic peaks have been obtained, which are listed in Table 1 along with their specific regions and corresponding species. Figure 3 represents the two spectra of CSi and CSii. No major differences have been found in these graphs, which confirms that RAFT agents have no affect or influence on the core-shell structure.

Identifying characteristic peaks of CSi and CSii particles.

S. No.Wave number (cm−1)Functional groupBelonging moleculeReferences
1.1,633C=O
2.1,583N–H (bending)
3.1,364C–NpolyAMPS[25]
4.1,190 and 1,039O=S=O (asymmetric and symmetric stretching)
5.603C–S stretching
6.3,333Vibration of bonded and non-bonded OH groupsH2ODisperse medium
7.2,957Stretching CH
8.1,726C=O stretchingBMA[27]
9.1,240C–O–C stretching

BMA, butyl methacrylate; polyAMPS, poly(2-acrylamido-2-methylpropane sulfonic acid).

Fig. 3

FTIR spectra of the CS particles.

The wave numbers axis in the FTIR spectrum of synthesized CSi and CSii is given in Figure 3, which indicates the presence of various functional groups due to the presence of their corresponding characteristic peaks. A peak present at 1,586 cm−1 illustrates the bending vibration of N-H, while peaks at 1,190 cm−1 and 1,039 cm−1 correspond to symmetric and asymmetric stretching of −SO2; moreover, other peaks at 1,633 cm−1, 1,364 cm−1, and 603 cm−1 illustrate the existence of C=O, C−N, and C−S, respectively. All these functional groups confirmed the existence of polyAMPS in CSi and CSii. Other peaks at 2,957 cm−1, 1,726 cm−1, and 1,240 cm−1 correspond to stretching vibration of functional groups of BMA, which are C−H, C−O−C, and C=O, respectively. Functional groups with their respective peak regions are listed in Table 1.

Thermogravimetric analysis of polyAMPS and core-shell particles

For studying the influence of RAFT agents on thermal degradation of their respective synthesized polymer, both polyAMPSi and polyAMPSii were analyzed via thermogravimetry, and a temperature increase rate of 30 °C/min was adjusted. The obtained thermogram gave two major degradations: (a) the one between 125 °C and 200 °C illustrates thermal degradation of sulfonic acid moiety [26, 28] (b) and the second one at 200–300 °C corresponds to polyAMPS chain burning. Initially, there is not much difference in the degradation rates of the two RAFT agents, but it appears at higher temperatures in later stages of thermogravimetric analysis. The degradation rate and extent in polyAMPSii are higher than those in polyAMPSi. A clear difference in thermal stability appears in the prepared polyAMPS after 230 °C, and it was observed that polyAMPSii lost its 70% weight at 243 °C compared to at 308 °C for polyAMPSi. After 300 °C, the thermal degradation is very small and the weight of the polyAMPSi and polyAMPSii remains stable. The thermogram given in Figure 4 and Table 2 shows relative high stability of polyAMPSi, which is surely due to the application of pyrrole-based RAFT agents, as reported by Stace et al. [29], as the dithiocarbamate-based RAFT agents are thermally more stable than other RAFT agents, which is basically due to presence of pyrrole and bidentate legends (SC(=S)N) [30]. These factors increase crystallinity along with thermal stability [29, 30].

Fig. 4

Comparing TGA results of polyAMPS. polyAMPS, poly(2-acrylamido-2-methylpropane sulfonic acid).

Comparative analysis of thermal degradation with respect to temperature.

PolymerTemperature (°C) with weight reduction
20%50%70%
polyAMPSi177242308
polyAMPSii131232243

polyAMPS, poly(2-acrylamido-2-methylpropane sulfonic acid).

Due to relatively high thermal stability of polyAMPSi, the corresponding CSi also showed high thermal stability, which is also elaborated by Figure 5 and Table 3. The thermogram showed three key weight decreases: the first one at 40–190 °C corresponds to complete dehydration [28]; the second degradation occurs in the range of 190–290 °C, which is specific for sulfonic acid groups in polyAMPS which produce sulfur oxide gases (SO2 and SO3) [26, 31]; and the third degradation was between 300 °C and 450 °C, which shows increased weight degradation of 76.757% for CSi and 76.269% for CSii. This major weight lost was due to deesterification [32], depolymerization, and denaturing of BMA [33], in which blazing of a hydro-carbon chain occurred and turned out into carbon monoxide, carbon dioxide, and traces of water vapor [34, 35]. Another major factor that enhances thermal stability of CSi was its relative high degree of crystallinity [36] since SC(=S)N (present in 4VP) has the capacity of being a bidentate legend [30]. A relative more pronounced XRD peak (Figure 6) supports this evidence.

Fig. 5

Comparative TGA results of CS particles.

Comparative analysis of thermal degradation with respect to temperature.

Core-shell particlesTemperature (°C) with weight reduction
25%50%75%92%
CSi340368392446
CSii302333352374

Fig. 6

Comparing XRD results of polymeric CS particles. XRD, X-ray diffraction.

XRD analysis of the core-shell particles

The XRD study revealed three major peaks: the first one was a more pronounced peak at 2θ = 18.82°, corresponding to a high degree of amorphous nature of both core-shell polymeric particles [37, 38], and the second and third peaks at 2θ = 37° and 45° a very small amount of crystallinity. The relative study revealed high crystallinity in CSi with respect to CSii, which is due to the presence of bidentate legends (SC(=S)N) in CSii [30].

EDX analysis of core-shell particles

In the EDX study, both core-shell polymeric particles confirmed the presence of all the expected elements with the abundance trend of C>O>S>K. The atomic and weight percentages with their corresponding species are illustrated in Figure 7. The comparative study revealed the resultant relative high carbon content in CSi, which is due to three main reasons: high degree of crystallinity, branching, and monomer conversion capacity in CSi [24].

Fig. 7

EDX result of polymeric core-shell particles.

Fig. 8

SEM images (highlighting spherical particles and crystals) of CSi. SEM, scanning electron microscopy.

Fig. 9

SEM images (highlighting spherical particles and crystals) of CSii. SEM, scanning electron microscopy.

SEM analysis
Analyzing article shape

The microscopic analysis of the resultant polyAMPS@BMA core-shell particles was nonuniform. Through SEM study a small portion of crystallinity and large amorphous nature with spherical particles shapes have been observed. Three different particle shapes have been obtained: spherical, spheroidal, and agglomerated. The shapes of the crystals are needle-like and block-like, with a diameter range from ~10 nm to 300 nm, which is due to crosslinking [39]. This irregular shape of resultant polyAMPS@BMA core-shell particles provided the advantage of high surface area for various purposes. The relative analysis concluded a high agglomeration in CSii. Particle size distributions (PSDs) are discussed in the following section.

Analyzing PSD and core-shell morphology

ImageJ (Java-based image processing program developed at the NIH, USA) software was used to analyze PSD and average particles size. From Figure 10 (left), it can be observed that the sizes of particles for CSi are between 200 nm and 500 nm, with an average size of 316 nm. Relative maximum particles have sizes ranging from 300 to 350 nm, followed by 250–300 nm. Relatively small amounts have sizes between 450 nm and 500 nm. The same software was used for CSii, for which particle sizes were distributed between 200 nm and 600 nm as illustrated in Figure 10 (right). Relative high numbers of particles were between 350 nm and 400 nm, with an average particle size of 392 nm. The reason behind average small particle sizes of CSi was the application of 4VP, since it has the capacity of hyper-branching, which results in smaller particle sizes. [24]

Fig. 10

Histograms of PSD of polymeric CS particles, where the histogram for CSi is on the left and for CSii is on the right. PSD, particle size distribution.

Figure 11 shows the scanning electron micrograph images of both core-shell particles. Since SEM analysis was done in bulk form without treatment with any chemical species, a prominent number of particles were found in agglomerated foam. Non-agglomerated and spherical particles are highlighted with white arrows. Core-shell morphologies have also been confirmed for SEM images. The white blurred portion of each spherical particle illustrates the shell, while the gray inner portion is the core of particles.

Fig. 11

Core-shell morphologies of obtained particles.

Conclusion

The basic purpose of this study was to evaluate the effect of RAFT agents on the net characteristics of the polyAMPS and their resultant core-shell particles. FTIR, XRD, EDX, and SEM studies confirmed the successful synthesis of the RAFT agents, polyAMPS, and polyAMPS@BMA particles. FTIR, XRD, and EDX studies authenticate that with the changing of RAFT agents, the structural properties of the resultant core-shell particles are less affected. The thermal properties, particle sizes, and yields are prominently influenced. Overall, it has been concluded that hyper-branched ability and crystallinity are the major factors that make the RAFT agents to influence the particle size, shape, size distribution, and thermal behavior of obtained polymers.

Fig. 1

Structures of the as-prepared RAFT agents. RAFT, reversible addition-fragmentation chain-transfer.
Structures of the as-prepared RAFT agents. RAFT, reversible addition-fragmentation chain-transfer.

Fig. 2

FTIR spectra of the as-prepared polyAMPSi and polyAMPSii. polyAMPS, poly(2-acrylamido-2-methylpropane sulfonic acid).
FTIR spectra of the as-prepared polyAMPSi and polyAMPSii. polyAMPS, poly(2-acrylamido-2-methylpropane sulfonic acid).

Fig. 3

FTIR spectra of the CS particles.
FTIR spectra of the CS particles.

Fig. 4

Comparing TGA results of polyAMPS. polyAMPS, poly(2-acrylamido-2-methylpropane sulfonic acid).
Comparing TGA results of polyAMPS. polyAMPS, poly(2-acrylamido-2-methylpropane sulfonic acid).

Fig. 5

Comparative TGA results of CS particles.
Comparative TGA results of CS particles.

Fig. 6

Comparing XRD results of polymeric CS particles. XRD, X-ray diffraction.
Comparing XRD results of polymeric CS particles. XRD, X-ray diffraction.

Fig. 7

EDX result of polymeric core-shell particles.
EDX result of polymeric core-shell particles.

Fig. 8

SEM images (highlighting spherical particles and crystals) of CSi. SEM, scanning electron microscopy.
SEM images (highlighting spherical particles and crystals) of CSi. SEM, scanning electron microscopy.

Fig. 9

SEM images (highlighting spherical particles and crystals) of CSii. SEM, scanning electron microscopy.
SEM images (highlighting spherical particles and crystals) of CSii. SEM, scanning electron microscopy.

Fig. 10

Histograms of PSD of polymeric CS particles, where the histogram for CSi is on the left and for CSii is on the right. PSD, particle size distribution.
Histograms of PSD of polymeric CS particles, where the histogram for CSi is on the left and for CSii is on the right. PSD, particle size distribution.

Fig. 11

Core-shell morphologies of obtained particles.
Core-shell morphologies of obtained particles.

Comparative analysis of thermal degradation with respect to temperature.

Core-shell particlesTemperature (°C) with weight reduction
25%50%75%92%
CSi340368392446
CSii302333352374

Identifying characteristic peaks of CSi and CSii particles.

S. No.Wave number (cm−1)Functional groupBelonging moleculeReferences
1.1,633C=O
2.1,583N–H (bending)
3.1,364C–NpolyAMPS[25]
4.1,190 and 1,039O=S=O (asymmetric and symmetric stretching)
5.603C–S stretching
6.3,333Vibration of bonded and non-bonded OH groupsH2ODisperse medium
7.2,957Stretching CH
8.1,726C=O stretchingBMA[27]
9.1,240C–O–C stretching

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