Materials Science for Energy Technologies 5 (2022) 311–323

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Materials Science for Energy Technologies

CHINESE ROOTS
GLOBAL IMPACT
journal homepage: www.keaipublishing.com/en/journals/materials-science-for-energy-technologies

Modification of PVC with captopril and complexation reaction for

preparing photostability and thermal stability of PVC
Taiseer Saleh a, Emad Yousif b, Emaad Al-Tikrity a, Muna Bufaroosha c,⇑, Amani Husain d,
Mohammed H. Al-Mashhadani b
a
Department of Chemistry, College of Science, Tikrit University, Tikrit 34001, Iraq
b
Department of Chemistry, College of Science, Al-Nahrain University, 64021 Baghdad, Iraq
c
Polymer Research Unit, College of Science, Al-Mustansiriyah University, Baghdad 10052, Iraq
d
Department of Chemistry, College of Science, UAE University, Al-Ain, UAE

a r t i c l e i n f o a b s t r a c t

Article history: Many chemical changes have been made to poly(vinyl chloride) (PVC) in order to enhance its photo-
Received 26 May 2022 stability features, the use of PVC in new applications, and the study of PVC-related phenomena. The
Revised 29 June 2022 chemical modification of PVC using captopril as a modifying agent is described in this paper. Infrared
Accepted 3 July 2022
spectroscopy and energy dispersive X-ray analysis was used to characterize the modified polymer.
Available online 7 July 2022
Metal salts (HgCl2, CoCl2, ZnCl2, NiCl2, and CdCl2) were used to react with the modified film and form
polymeric complexes. FTIR, weight loss percentage, AFM, EDX, and SEM approaches were used to analyze
Keywords:
polymeric films that had been exposed to UV radiation for 300 hrs. The modified PVC complexes films
PVC
Captopril
have shown excellent stability against photo-degradation even after 300 h of irradiation by UV light.
Photostability Thermogravimetry (TGA) was used to evaluate the thermal characteristics of the modified polymers,
Thermal stability which demonstrated that the synthesized polymer complexation showed good thermal stability.
Weight loss Ó 2022 The Authors. Publishing services by Elsevier B.V. on behalf of KeAi Communications Co. Ltd. This is
an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

1. Introduction produce the Bunte Salt [15] has also been proved to be effective.
Chemically modifying polymeric surfaces is one technique to attain
PVC (polyvinyl chloride) is one of the most widely used poly- this aim. Aromatic thiol compounds have long been known to be
mers around the world, hence it’s mostly utilized in the plastics the most effective nucleophiles for PVC modification [16–19].
industry. Despite the fact that it is a low-cost polymer, PVC has When the right reaction conditions are used, these chemicals
poor heat stability. While most PVC products require a molding may be integrated into the polymer with high conversions and
temperature over 180 °C, the polymer begins to deteriorate around no secondary reactions. Furthermore, this sort of reaction has been
120 °C. As a result, before the molding process, the polymer should proven to be stereoselective and may be carried out in solution,
be thermally stabilized because degradation causes the polymer to melt, suspension, or preferentially at the surface of a polymer film
be yellow due to the synthesis of unsaturated polyenes and the [20–24]. Captopril is a nontoxic, white, inexpensive aliphatic car-
generation of HCl gas [1]. Thus, before the molding process, labile boxylic acid with heteroatoms (nitrogen, oxygen, and sulfur). It
sites such as chlorine atoms should be substituted with more has a little sulfurous odor and a melting point of 103 °C to
stable units. Chemical modification [2–5], or just mixing different 104 °C [25]. Captopril is projected to function as an effective PVC
thermally stable chemicals [6,7] are all examples of this. The chem- addition due to its high heteroatom concentration (29.5 percent
ical modification of PVC in solution by nucleophilic replacement of by weight). Additionally, captopril is harmless and will not pollute
its chlorine atoms is well recognized [8–10]. PVC may be modified the environment after its use. All of these attempts to make cova-
easily with the formation of PVC–R while R is highly electronega- lently bonded PVC-plasticizer systems had one major flaw which is
tive atoms such as N, O, or S [11]. Nucleophilic substitution using they were commercially unviable. To be effective in this regard, the
thioethers and thiols has been shown to work well [12]. In addi- selected chemistry must be both economically and environmen-
tion, the use of dithiocarbamates [13], NaN3 [14], and Na2S2O3 to tally sustainable, as well as meet the following requirements such
as ease of preparation, quantitative coupling to the polymer, and
high plasticizer efficiency. The synthesis and characterization of
⇑ Corresponding author. PVC modified with captopril with a variety of metal salts utilizing
E-mail address: [email protected] (M. Bufaroosha).

https://doi.org/10.1016/j.mset.2022.07.001
2589-2991/Ó 2022 The Authors. Publishing services by Elsevier B.V. on behalf of KeAi Communications Co. Ltd.
This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).
T. Saleh, E. Yousif, E. Al-Tikrity et al. Materials Science for Energy Technologies 5 (2022) 311–323

reflux are shown in this study, and these compounds may be 2.5. Measurement of PVC functional group indices
employed as efficient inhibitors of PVC photodegradation.
After photodegradation of PVC, residues containing carbonyl
and alkene fragments are formed. The increase of peak absorptions
2. Experimental produced by photo-irradiation for made fragments may be tracked
utilizing FTIR and calculate the indices regarding to the unaffected
2.1. Materials peak by radiation such as C–H peak [26]. Equation (1) was used to
obtain the indices of carbonyl and alkene fragments (Is), where As
Petkim Petrokimya company provided the PVC (Istanbul, Tur- and Ar are the intensity of the functional and reference groups,
key). Aldrich provided captopril, all metal salts, and solvents, respectively.
which were utilized without additional (Schemes 1 and 2)
purification. IS ¼ AS =Ar ð1Þ

2.2. Instrument 2.6. Measurement of PVC weight loss

A Shimadzu FTIR 8300 spectrophotometer was used to record Due to the removal of volatile compounds, PVC photodegrada-
the FT-IR spectra. A TESCAN FE-SEM MIRA3 system was used to tion causes weight loss [27]. Equation (2) may be used to compute
capture the scanning electron microscopy (SEM) pictures. A Veeco the weight loss (percentage) from the weight of the sample pre-
device was used to obtain the atomic force microscopy (AFM) pic- (Wpre) and post-irradiation (Wpost).
tures. The PVC films were exposed to UV radiation using the

Weight loss ð%Þ ¼ W pre X W post =W pre X 100 ð2Þ
weather-meter QUV accelerator.

2.3. Preparation of PVC-ligand film (modified PVC film) 3. Results and discussions

A glass plate (4 * 4 cm2) comprising 20 holes with a thickness of 3.1. Synthesis of modified polymer
about 40 mm was poured with 5 g of PVC dissolved in 100 mL of
THF as the solvent. By keeping the plate at 25 °C for 18 h, the sol- The reaction between PVC film and captopril in THF as solvent
vent was eliminated. The films were dried for 18 h in a vacuum under reflux for 3 h gave a new compound as a film. The reaction
oven at 25 °C, then dissolved in THF 0.5 g of captopril added and began with a nucleophilic attack by sulfur atoms on the carbon
refluxed for 3 h with stirring. The resulting homogeneous solution in the polymeric chain transporting the chlorine atom, followed
was put into the same glass plate. by chloride anion exit as a suitable leaving group. [28–31]. FTIR
of PVC + Captopril shows a peak at 2972 cm1 consisting of the –
CH2, and –CH asymmetric stretching vibration at the same time
2.4. Preparation of PVC-ligand-M(II) complex films the spectrum shows a peak at 3656 cm1 assigned to –OH of car-
boxyl group in captopril, the spectrum shows disappearing of –
A 0.3 g of synthesized modified polymer (PVC-L) dissolved in SH group absorption at 2565 cm1, a peak appears at
5 mL of THF and 0.0421 g of cadmium chloride (dissolved in pyri- 1733.89 cm1 consisting to the C = O carbonyl group in carboxyl
dine) were mixed, refluxed for 3 h and the obtained solution was (asymmetric) another peak at 1639.39 cm1 belong to C = O in
poured in the glass plate. amide and at 1431 for C = O (symmetric) from amide group.

Scheme 1. Synthesis of modified PVC film.

Scheme 2. Synthesis of PVC-L-M(II) complexes.

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Fig. 1 shows FTIR spectra of Captopril unit and the modified poly- quency of the asymmetric carbonyl group shifted to lower, signify-
mer (PVC-L). ing that the bonding occurs between the metal and the hydroxyl
group oxygen of carboxylic acid of the ligand. The difference [Dv
3.2. Preparation of PVC-ligand–metal complexes films (asym-sym)] between the asymmetric (asym) and symmetric
(sym) vibration frequency of carbonyl of the carboxyl group was
In recent times, scientists have investigated altering PVC chem- more than 260 cm1, which means the ligand was asymmetry
ical structure by attaching aromatic and/or heterocyclic moieties bidentate. New peaks appear in FTIR data for complexes assigned
via halogen displacement reactions [32]. The removal of facial to v (Ni–C), v (Cd–O), v (Hg–O), (Co–C) and v (Zn–O) as shown in
chlorine from PVC is considered to increase the possibility of ligand Table 1 and Fig. 2.
simplicity binding to the PVC matrix [33]. When halogen is used as
a displacement agent, SN2 is thought to be the process for produc- 3.3. Investigation of PVC photodegradation through FTIR
ing modified PVC by aromatic or heterocyclic compounds. The spectrophotometry
modified polymer (PVC-L) dissolved in THF and a metal chloride
were mixed, refluxed for 3 h and obtained solution was poured Aldehydes, ketones, and alkenes are the most prevalent oxy-
in the glass plate. FTIR of final films shows the broadness of the genated products obtained after irradiation of PVC by UV light.
carboxylic group peak for the ligand change, and the vibration fre- After irradiation, carbonyl-containing fragments are frequently

Fig. 1. FTIR spectra of a) starting compound Captopril (L) b) modified PVC-L.

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Table 1
FTIR data of modified polymer (PVC-L) and polymeric complexes (PVC-L-M).

Compounds Wave number cm1

C = O (sym) C = O (asym) Dv(asym-sym) MO
PVC-L 1431 1639 208 –
PVC-L-Hg 1431 1722 291 380
PVC-L-Co 1431 1724 293 400
PVC-L-Zn 1431 1722 291 410
PVC-L-Ni 1431 1722 291 405
PVC-L-Cd 1431 1722 291 420

Fig. 2. FTIR spectra for PVC-ligand-Cd(II) complex film.

2
1.8
1.6
PVC
1.4
1.2 PVC-L
I C=O

1 PVC-L-Ni
0.8 PVC-L-Co
0.6 PVC-L-Cd
0.4
PVC-L-Hg
0.2
PVC-L-Zn
0
0 50 100 150 200 250 300
Irradiaon Time (h)

Fig. 3. IC=O indices versus Irradiation time of PVC films.

detectable using an FTIR pattern. As a result, PVC films were of PVC advances. As a result, throughout the irradiation process,
exposed to UV light for various durations of time and the FTIR FTIR technique was utilized to investigate the development of
spectra were then collected. The FTIR spectra of the blank and the intensity of these peaks C = O (1710 cm1) and C = C
modified PVC after irradiation shows the production of carbonyl (1612 cm1). In comparison to the C–H bending vibration bonds
and alkene fragments develops more noticeable as the irradiation (1331 cm1), the absorptions of these groups have risen signifi-

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1.6

1.4

1.2 PVC
PVC-L
I C=C 1
PVC-L-Ni
0.8
PVC-L-Co
0.6
PVC-L-Cd
0.4
PVC-L-Hg
0.2
PVC-L-Zn
0
0 50 100 150 200 250 300
Irradiaon Time (h)
Fig. 4. IC=C indices versus Irradiation time of PVC films.

2.5

2
PVC
Weight Loss%

1.5 PVC-L
PVC-L-Ni
1 PVC-L-Co
PVC-L-Cd
0.5
PVC-L-Hg
PVC-L-Zn
0
0 50 100 150 200 250 300
Irradiaon Time (h)

Fig. 5. Weight Loss (%) versus Irradiation time of PVC films.

cantly with irradiation time, while C–H group is unaffected by UV and the PVC films were removed from the chamber after 300 h.
radiation. During irradiation, the indices of C = O (IC=O) and C = C The data shows that the modified PVC film loses more weight than
(IC=C) fragments of modified PVC film and complexes were calcu- the modified film that interacts with metal salts, which loses the
lated using Equation (1). Figs. 3 and 4 depict the changes in IC=O least amount of weight. The acquired results demonstrated that
and IC=C for modified PVC under UV light, respectively. For modified the modified PVC sample lost weight when compared to modified
PVC, the alterations in the IC=O and IC=C were clearly higher in com- PVC samples that had been exposed to metals, particularly the
parison to complexes, but it is still better than blank PVC. The novel PVC-L-Hg. As shown in Fig. 5, these results are in good accord with
synthesized polymeric complexes served as PVC photo stabilizers prior work in which various ligands were utilized to change PVC
by reducing the production of tiny groups having carbonyl and structure and used as photo stabilizers [34–36].
alkene fragments.

3.5. Atomic force microscopy (AFM) to investigate surface morphology

3.4. Investigation of PVC photo degradation through weight loss of PVC

During the irradiation process, the PVC films were weighed. The The surface morphology of modified PVC and polymeric com-
measurements were taken every 50 h with an analytical balance, plex PVC films was investigated using atomic force microscopy

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Fig. 6. AFM images of a) PVC-L, b) PVC-L-Cd, c) PVC-L-Ni, d) PVC-L-Hg, e) PVC-L-Zn, f) PVC-L-Co.

(AFM). AFM may be used to determine the properties and rough- with metals enhanced the stability of the modified films consider-
ness of the film surface. Bond breaking occurs during long-term ably. The irradiation films of five synthesized complexes have a
irradiation of modified PVC, resulting in a rough and fragmented smoother surface than the blank modified PVC film. The modified
surface [37,38]. Fig. 6 shows topographic AFM images of the films’ PVC-L, PVC-L-Hg, PVC-L-Ni, PVC-L-Zn, PVC-L-Cd, and PVC-L-Co
surface after 300 h of irradiation. The interaction of modified film films had roughness factors of 16.39, 10.46, 7.24, 5.41,3.52, and

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Fig. 6 (continued)

2.51, respectively. In addition, this increases the Rq superior to that facet-chain period, and polymer concentration, according to a
seen with several previous PVC additions [40–44]. number of researchers [49].

3.7. Light microscopic images to investigate surface morphology of PVC

3.6. Scanning electron Microscope (SEM) to investigate surface
morphology of PVC When comparing pre-irradiation and post-irradiation pho-
tographs of the surface of PVC films, imperfections would be seen
The impact of UV irradiation on the surface morphology of in the microscopic images as described in Fig. 8. After irradiation,
changed films was investigated using Scanning Electron Micro- the number of fractures, black stains, and grooves becomes more
scope (SEM) [45]. This technique was used to analyze the surface evident. The release of HCl as a result of PVC degradation causes
morphology of changed films; the SEM topography was thoroughly the black patches to emerge [50]. In comparison to the modified
explored to investigate the effects of UV light exposure on PVC film film, the surface of the modified film containing Zn(II), Hg(II), Cd
samples as an effective tool for diagnosing particle size and shape (II), Ni(II) was practically smooth, with fewer grooves or fractures
[46,47]. Fig. 7 depicts the SEM images of modified PVC with capto- and a notable shift in color. The surface of the blend containing
pril (PVC-L) and its complexation with different metals (PVC-L-M) Co(II) has some dark patches and abnormalities; it’s unclear why
after irradiation by UV light for 300 h. As a result of the interaction/ this film has more grooves and a darker hue; it might be related
coordination that occurred between the modified films and Co(II), to the pace at which volatiles are eliminated during the photo
Hg(II), Zn(II), Cd(II), and Ni(II) ions as a result of pass-linking, we degradation process.
can fairly assume that this roughness at the film surface is due to
this interaction/ coordination. However, a number of circular holes 3.8. Energy dispersive X-Ray analysis (EDX)
were discovered on the surface, which was most likely caused by
the fast evaporation of THF, which had been used as a solvent in The Energy Dispersive X-ray (EDX) method was used to investi-
the film-making process. The pore size was altered as a result of gate the modified polymer elemental composition. Fig. 9 shows the
the difference or variation in what is called deriving forces during EDX charts of modified PVC films and their complexes. The Cl peak
phase separation [48]. The form of the honeycomb is heavily reli- in the modified film has sufficient modification due to the substi-
ant on a variety of parameters, including the solvent type, polymer tution interaction of chlorine atoms with S in the thiol group.

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Fig. 7. SEM of a)PVC-L, b)PVC-L-Cd,c) PVC-L-Ni, d) PVC-L-Hg, e) PVC-L-Zn, f) PVC-L-Co.

EDX also demonstrates the existence of metals in complex poly- film in Fig. 10 reveals that this film lost about 56.33 percent of
meric films. its weight at 240.31 °C, which may be because the adsorbed sol-
TGA/DSC measures temperature-related material properties vent on the compound was removed. Afterward, it exhibits a
like mass loss, melting points, and other phase transition tech- weight loss of 24.51 percent at a rapid stage at 446.81 °C. The
niques that can be used to investigate the weight loss of polymers weight change of the compound at 600 °C is about 80.83%. TGA
by raising the temperature. The DSC/TGA curve for modified PVC curve of PVC-L-Cd shows that the film lost 67.31 % from its weight

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Fig. 7 (continued)

at 269.31 °C, another peak showed 20.47% weight loss at 445.74 °C, 289.54 °C, weight change at 600 °C was 53.55%. PVC-L-Zn shows
weight change at 600 °C is 87.78%, for PVC-L-Ni a peak shows a weight loss of 51.01% up to 259.71 °C. After that, in one step
62.97% weight loss at 254.99 °C and 28.69% weight loss at and up to 463.56 °C, it loses another 14.52% of its weight. At
443.33 °C, at 600 °C, the weight change is 91.66 %, while PVC-L- 600 °C the weight change of this film is about 65.53%, PVC-L-Co
Hg TGA curve shows one peak of weight loss 46.45% at shows that it has lost about 57.16% of its weight at 273.41 °C.

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Fig. 8. Microscope images of a) PVC-L, b) PVC-L-Cd, c) PVC-L-Ni, d) PVC-L-Hg, e) PVC-L-Zn, f) PVC-L-Co.

The film then loses about 23.97% of its weight at 445.82 °C. The showed good photo-degradation resistance. Thermogravimetry
weight change amount of the compound at 600 °C is about 81.12%. (TGA) was used to assess the modified polymers’ thermal proper-
ties, which showed that the synthesized modified polymer com-
4. Conclusions plexation was thermally stable, as proven by the starting
breakdown temperatures.
To conclude, in this research, it describes the chemical modifi-
cation of PVC utilizing captopril as a modifying agent. The modified CRediT authorship contribution statement
polymer was characterized using infrared spectroscopy and energy
dispersive X-ray analysis. To react with the modified film and cre- Taiseer Saleh: Conceptualization. Emad Yousif: Conceptualiza-
ate polymeric complexes, metal salts were utilized. Polymeric films tion. Emaad Al-Tikrity: Writing – original draft. Muna Bufa-
that had been exposed to UV radiation for 300 h were analyzed roosha: Writing – review & editing. Amani Husain: Writing –
using FTIR, weight loss percentage, AFM, EDX, and SEM methods. review & editing. Mohammed H. Al-Mashhadani: Writing – orig-
Even after 300 h of UV irradiation, the modified PVC complexes inal draft.

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Fig. 9. EDX for: a) PVC-L, b) PVC-L-Cd, c) PVC-L-Zn, d) PVC-L-Hg.

Fig. 10. TGA analysis: a) PVC-L b) PVC-L-Cd c) PVC-L-Ni d) PVC-L-Hg e) PVC-L-Zn f) PVC-L-Co.

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Further reading
from arborescent graft polystyrenes via the breath figures method, Polymer
107 (2016) 273–281. [39] E. Yousif, A. Hasan, G.A. El-Hiti, Spectroscopic, physical and topography of
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