Natural weathering of plasticized polyvinyl chloride (PVC) Stabilized

with Epoxidized Sunflower Oil.

FARID. HAMITOUCHE a,b, NADIA. LARDJANE a,b*, YVES. GROHENS c, HASSIBA. HABCHI.

LARIBI d, NAIMA. BELHANECHE. BENSEMRAb

aFaculty of Biological Sciences and Agronomic Sciences. Mouloud Mammeri University, Tizi-Ouzou,

ALGERIA

bLaboratoire des Sciences et Techniques de l’Environnement, Ecole Nationale Polytechnique, BP 182

El-Harrach, Algiers, ALGERIA

cUniversité de Bretagne-Sud, Institut de Recherche Dupuy De Lôme (iRDL), CNRS, UMR

6027,Centre de Recherche de St Maudé, B.P. 92116 - 56321 Lorient Cedex, FRANCE

dLaboratory of Chemical Engineering, Department of Process Engineering, Faculty of Technology,

University of Blida 1, ALGERIA

Abstract: - The aim of this work is to study the inﬂuence of the weathering conditions on the degradation level

of stabilized PVC. Epoxidized Sunflower oil (ESO) was used as a new biodegradable stabilizer for PVC.

Flexible plasticized formulations (40% plasticizer) were realized, the natural weathering of the PVC samples

was investigated. The samples were exposed in Tizi Ouzou (Algeria) for nine months. The samples were

characterized by Fourier transform infrared spectroscopy in order to follow the structural changes. Moreover,

the variation of the mass of the samples, the variation of density and mechanical properties (tensile and shore D

hardness) were taken into account. Samples were characterized in terms of morphology by SEM. The best

results were obtained with the formulation containing DINA and ESO compared to the traditional formulation

containing DOP and ESO.

Key-Words: - PVC, ESO, natural weathering, DINA, DOP.

Received: March 21, 2021. Revised: February 4, 2022. Accepted: March 2, 2022. Published: April 6, 2022.

1 Introduction

Poly Vinyl Chlorid (PVC), which will be the subject

of our study, has a long history of development

which began almost 100 years ago with the

patenting of the concepts of emulsion and

suspension polymerization, the development of the

industrial process for synthesizing vinyl chloride,

and patents on its plasticization, followed by the

development of stabilization about 75 years ago [1].

PVC is one of the most important and widely used

thermoplastics due to its many valuable properties

such as: low price, good processability, chemical

resistance and low flammability. It is approved for

use as films and seals for cork bottles in general

contact applications [2]. Phthalates are a class of

chemicals substances used as plasticizer for the

PVC. They have the particularity to confer certain

flexibility to plastics. They are found in products as

diverse as paints, synthetic inks and fragrances,

drugs, medical devices, food packaging, toys, etc. In

1973, 93% of plasticizers in PVC were phthalates.

The most commonly used are: di-ethylhexyl

phthalate (DEHP), di-isodecyl phthalate (DIDP) and

di-isononyl phthalate (DINP) [3, 4].

Phthalates are toxic substances that compromise

immune function, the endocrine and reproductive

systems, neural and physical development, as well

as the increased risk of cardiovascular disease [5-7].

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Stabilizers are indispensable to provide the

necessary stability of the PVC against heat, light

and weathering [8]. Indeed, When Polyvinyl

chloride (PVC) is exposed to high temperatures

and/or UV irradiation in the presence of oxygen,

free radical chain reactions take place leading to

scission and/or crosslinking of the polymer chains

and consecutively to a deterioration of the polymer's

physical structure [6-10]. The rate of thermal

degradation can be reduced by the addition of

thermostabilizers to a level which is acceptable from

a technological point of view [10-12]. Addition of

stabilizers to PVC may improve its photostability

[13-15]. Applicable stabilizers are heavy metal and

organotin compounds as well as organic co-

stabilizers, depending on the desired product

properties [16]. Lead is also considered to be an

endocrine disruptor and may affect the reproductive

function of both men and women. In the human

body, this metal is mainly found in the form of

inorganic compounds: on the one hand in the

respiratory system, in the form of aerosols

containing lead (absorption by the lungs) on the

other hand through food and drink (absorption from

intestine and the stomach). It is a cumulative

toxicant that can cause neurological and

hematological disorders known as lead poisoning.

The risk of lead poisoning is higher in young

children, especially 1 to 3 years old [17].

The aim of this work is to pursue the study of the

inﬂuence of the weathering conditions on the

degradation level of pasticized PVC. New

formulations based on PVC in order to preserve the

environment were realized, di-iso nonyl adipate

(DINA) was used as a substitute plasticizer for

phthalates and sunflower oil was used in order to

replace lead stabilizers.

2 Experimental

2.1. Materials

2.1.1. PVC resin

Shintech SE 1200 grade 1 is a PVC resin produced

by the American company INC-USA, polymerized

in suspension.

2.1.2. The plasticizers

The plasticizers (DOP and DINA) used in the

preparation of the different formulations are

provided by the general society of plasticizers

(Tunisia).

2.1.3. Epoxidized Sunflower Oil (ESO)

Commercial suspension PVC resin, Shentech 1200

(American company INC-USA), with K value 71.1

according to DIN 53 726 and Mn= 78700 was used.

Zn and Ca stearates complex (Reapak BCV/3037)

from IACN (Italy) and epoxidized soya bean oil

(ESBO) from Akdeniz Kimya A.S. (Turkey) are

commercial products used as received. Epoxidation

of sunflower oil was carried out at 50 °C in a 250 ml

three-necked flask fitted with a condenser, a

mechanical stirrer, and a thermometer; using the

peracetic acid prepared in situ by reacting 20 ml of

hydrogen peroxide (30 % V / V) and 20 ml of

commercial sunflower oil (100%) with an excess of

glacial acetic acid in the presence of Amberlite IR

120. The reaction medium is stirred and heated for 2

hours. Subsequently, we proceeded to the

decantation of the solution and removing the

aqueous phase, then washing the oily phase with

distilled water until the acid phase is purified (pH =

7) [18].

2.2. Preparation of PVC Films

The resin and the additives were mixed: 100 g of

PVC, 2 g of Zn and Ca stearates complex, 5 g of

ESO or ESBO, 1 g of stearic acid and 40 g of DOP

or DINA. The obtained mixture was then introduced

into a rotary two- roll mill (Lescuyer S.A, France)

heated at 140 ° C for 15 minutes. The mixture is

then placed between two trays of a tabletop press

(Fontigine BV, Holland) to obtain the desired

thickness (2 ± 0.1 mm).

2.3. Natural Weathering

The PVC samples were mounted on metallic plates

(Tizi-Ouzou, Algeria) placed facing southwards in a

45° angle with the plane of the earth as per ASTM

D1435-99 [19]. The PVC samples subjected to the

natural weathering exposure (November 2016- July

2017) were cut from a larger sheet measuring 100

mm x 100 mm. The exposure site is located at an

elevation of 153.40 m, its latitude North is 36 ° 43'

and longitude East 04° 1'. The samples were

periodically taken out and characterized. The rate of

variation of the mass was determined as a function

of time following the relation:

mt – m0

X 100

ζ (%) =

……………(1)

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Where m0 is the initial mass sample at the time t0

and mt is the mass of the sample at the time t (after

natural weathering).

2.4. Sample Characterization

2.4.1. Physical Properties

The density was measured according to the

ISO/ R1183, using DSM densimeter (Lhomargy

S.A, France).

2.4.2. Mechanical Properties

The tensile properties were measured using MTS

Criterion model 42 testing machine (MTS

Systemes, France), strained at a rate of 100 mm/min

according to T51-034 standard.The Shore D

hardness was measured using Exacta Bareiss Shore

D durometer (Prolabo, Germany) according to NFT

51-109 standard. The results from mechanical

testing are presented as average values of three

measurements for each type of sample. The

determination of the Residual thermal stability at

200 ± 1 °C was carried out according to the standard

ISO 182-2. The weight of the samples was 0.5 g.

The time required to the appearance of red colour in

the pH- paper is associated to the stability

determined by (pHs) expressed in minutes.

2.4.3. FTIR Analysis

The weathered PVC samples were analyzed

directly by FTIR spectroscopy in ATR mode by

using a Jasco FT/IR-4200 spectrophotometer

(Jasco Inc, Easton MD, USA). Spectra were

collected in the spectral range of 4000 to 400

cm-1, using 60 scans at a resolution of 8 cm-1.

2.4.4. Thermal Properties

2.4.4.1. Residual Thermal Stability

The determination of the Residual thermal stability

at 200 ± 1 °C was carried out according to the

standard ISO 182-2. The weight of the samples was

0.5 g. The time required to the appearance of red

colour in the pH- paper is associated to the stability

determined by (pHs) expressed in minutes.

2.4.4.2. Thermogravimetric Analysis.

Thermogravimetric analysis leads to evaluate the

mass loss, thermal stability and rate of

decomposition that a sample undergoes during heat

treatment as a function of temperature. The

thermograms of the various samples were recorded

using a LINSEIS STA PT 1600 type

thermogravimetric device, controlled by a

microcomputer. The mass loss is measured using a

thermobalance under an inert nitrogen atmosphere

in a temperature range of 20 to 700 ° C with a

heating rate of the order of 20 ° C / min.

2.4.5. Morphology Analysis

The PHILIPS ESEMXL30 scanning electron

microscope with tungsten filament was used. It is

coupled with a complete system of

microanalysis EDS-X (Energy Dispersive of X-

Rays, Belgium). The surfaces were prepared by

cutting the samples (5 mm, Rotation: n x 360°).

A wet mod at 10 mbar H2O vapor at the voltage

of 20 KV was chosen for observation; the signal

was recorded using a detector for bakscaterred

electrons.

3 Results and discussion

3.1. Variation of mass

According to the mass variation results (table

1), It can be noted a significant increase in mass

variation rate as a function of natural ageing

time, which explains penetration of water in the

different sample; this is due to the quantities of

rainfalls measured in the area (table 2).

Table 1. Mass variation as a function of natural

weathering time

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Table 2. Climatic data of the study region (Tizi

ouzou, Algeria).

3.2. Variation of Physical and Mechanical

Properties

Table 3 shows that the density increases in the case

of the three considered formulations, which explain

the loss of the plasticizer.

Table 3. Variations of density as a function of

natural weathering time.

Figures 1, 2 and 3 indicate the mechanical

properties of the PVC sample as function of natural

weathering time. We can see a decline in the

elongation rate during the 09th month of the natural

ageing. These variations may be due to an eventual

loss of plasticizer which reduced the flexibility of

the samples and/or to the structural modiﬁcations

that occurred in the polymer backbone upon aging

[20]. The decrease of the stress at break induced by

the weathering is generalized at all PVC

formulations, these results are in agreement with

those obtained in similar studies [21-23]. They show

that chain scission reactions occurred during the

exposure of the samples to natural weathering.

However, the shore D hardness decrease during the

third months of the natural ageing in the case of the

samples containing DOP; this is due probably to the

absorption of water (525,3 mm/year) which

conferred to the samples a light plasticization [24].

For the samples Containing DINA, the shore D

hardnes increased during the period of the natural

weathering, which indicate the loss of the

plasticizer. The total inﬂuence of weathering can be

considered as a composite effect of solar UV

radiation, moisture and temperature. The climatic

data of the study region (Tizi ouzou, Algeria) are

presented in table 2. Numerous studies indicate that

this change is linked to the thermal decomposition

and photooxidation of PVC [20]; and to the

chemical changes in the surface and internal

oxidation [25].

FIG.1 Evolution of the elongation at break as a

function of natural weathering time.

FIG.2 Evolution of the stress at break as a

function of natural weathering time.

Density (g/cm3)

Time

(months)

P (DOP, ESO)

P (DOP, ESBO)

P (DINA, ESO)

1,2 ± 0,000

1,16 ± 0,000

1,22 ± 0,000

1,2 ± 0,000

1,22 ± 0,000

1,2 ± 0,000

1,24 ± 0,000

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FIG.3 Evolution of the shore D hardness as a

function of natural weathering time.

3.3. FTIR Analysis

In order to explain the PVC aging results, the

samples were analyzed by infrared spectroscopy.

The different additives containing in the different

samples of PVC were characterized (table 4) [26-

29].

Table 4 Characteristic bands of the additives

present in PVC film

The results of the FTIR analysis show the:

- Appearance of a new bands at 1627 cm-1

and 1667 cm-1 due to the formation of

conjugated double bonds. Our results

corroborates with those fond by

Chaochanchaikul and al., which indicates

that the polyene contents of PVC were

found to increase with increasing

weathering time [30].

- Appearance of a new bands at 1889 cm-1 in

the case of the samples containing DINA

and ESO due to the formation of

conjugated double bonds (figure 4);

- Appearance of a new band between 3200

and 3500 cm due to hydroxyl compounds

(alcohols, carboxylic acids, hydroperoxides)

which are associated with chain scissions

that occurred during aging of the samples;

- Disappearance of the band at 3455 related to

the chain scissions after three months of

natural weathering in the case of the

samples containing DOP and ESBO, and

after six months for the formulation

containing DOP, ESO and DINA, ESO;

- increase of the absorbance ratios (table 5) of

the new bands formed during aging

A1627/A1426 and A1654/ A1426 , in the

case of samples containing DOP, ESBO and

DINA, ESO, which is due to an increase of

the concenration of conjugated double

bonds and thus indicates that the

dehydrochlorination of PVC occurred [20].

- Decrease of the absorbance ratios A1726/

A1436, 1466/1436 and A1337/ A1436 and

A1130 /A1436 with time of aging. The

decrease can be explained by the loss of

additive.

FIG.4 FTIR spectra of PVC samples containing

ESO and DINA after various times of natural

weathering.

n°

Wave

number [cm-1]

Assignment

Additive

1726

1466

1337

1130

C = O (ester)

CH2 (methyl, methylene)

CO2 - (carboxylic acid salts)

C-O-C

ESO, ESBO, DOP and DINA

ESO, ESBO, Zn and Ca stearates complex,

DOP and DINA

Zn and Ca stearates complex

ESO, ESBO

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Table 5 Variations of absorbance ratios as a

function of time of natural weathering.

3.4. Thermal Properties

3.4.1. Residual Thermal Stability

The residual thermal stability varied as a function of

the weathering time in the case of all the considered

formulations. The thermal stability of samples

plasticized by DOP is relatively greater compared to

samples plasticized by DINA (table 6). This

difference can be explained by the amount of heat

stabilizers still active in the sample. In fact, during

the preparation of the formulations, a certain amount

of stabilizers is consumed following chemical

reactions with the HCl released by the PVC and is

transformed into an inactive form (ZnCl2, CaCl2, -

CHCl-CHOH-). Therefore, the determination of the

residual thermal stability provides information on

the amount of thermal stabilizer still active in the

PVC sample. It is known that the plasticizer allows

better homogenization of the constituents of the

formulation and, consequently, better efficiency of

the stabilizing system. Thus, the obtained results

show that because of its linear structure and its low

viscosity, the DINA allowed the best

homogenization of the constituents of the

formulation and the best efficiency of the stabilizing

system, hence the smaller amount of active thermal

stabilizers and the lowest residual thermal stability.

On the other hand, DOP contains steric hindrance

linked to the presence of an aromatic ring in its

structure, resulting in less efficient homogenization

of the constituents of the formulation, less efficiency

of the stabilizing system and a greater quantity of

still active thermal stabilizers, which resulted in the

increase in residual thermal stability. In addition, it

can be noted that the residual thermal stability

decreased in the case of all the considered

formulations, which suggests that the phenomena of

degradation of the thermal stabilizers was occurred

[3, 31, 32].

Table 6 Variation of residual thermal stability

at 200°C as function of natural weathering time.

3.4.2. Thermogravimetric Analysis (TGA)

The derivatograms recorded under a nitrogen

atmosphere (Figure 5) for plasticized simples after

nine months of natural weathering are similar. The

mass loss was recorded at 205 °C for the samples

plasticized by DOP and 208 °C in the case of the

samples plasticized by DINA, the mass loss

accelerated at 286-450 °C. The first stage (200-250)

corresponds to the dehydrochlorination of the

polymer [33, 32]. In the first step the temperature of

maximum weight loss is important in the case of the

samples plasticized with DINA compared to the

samples containing DOP, this result leads to say that

the formulation based on DINA and ESO is more

stable. The peak at 450 is produced by PVC

decomposition [34].

3.5. Visual Observation

After various time of natural weathering (figure

6), a gradual change in colour can be observed

in the case of the three plasticized samples

probably related to the degradation,

dehydrochlorination of PVC, and dust buildup

on samples during natural weathering [35].

Furthermore, there is a considerable change for

samples containing the DINA and epoxidized

00 months

03 months

06 months

09 months

DOP, ESBO

1726/1436

1466/1436

1337/1436

7.828

0.934

2.460

1.000

0.747

2.315

0.767

0.863

2.390

0.815

0.684

1130/1436

1618/1436

1654/1436

2341/1436

2368/1436

3455/1436

1.131

1.043

0.660

1.130

1.347

0.313

1.217

1.821

0.136

0.231

1.445

0.434

0.510

0.434

DOP, ESO

1726/1436

1466/1436

1337/1436

1.297

0.650

0.505

2.830

1.000

0.648

2.67

0.829

0.975

1.844

0.333

0.688

1130/1436

1618/1436

1654/1436

2341/1436

2368/1436

3455/1436

0.650

0.648

0.507

0.804

0.945

1.14

2.207

0.682

0.182

0.207

0.243

1.333

1.000

0.511

DINA, ESO

1726/1436

1466/1436

1337/1436

2.730

0.915

2.781

1.096

0.866

2.505

0.811

0.905

2.109

0.619

0.523

1130/1436

1618/1436

1654/1436

1984/1436

2341/1436

2368/1436

3455/1436

0.866

0.278

0.296

0.509

0.545

1.23

1.811

0.529

0.576

0.117

0.165

0.211

0.523

0.519

0.571

0.333

0.285

0.271

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sunflower, which shows the degradation of the

polymer by the phenomenon of photo oxidation

[36].

FIG.5 ATG and DTG curves recorded under a

nitrogen atmosphere for the PVC samples after nine

months of natural weathering.

FIG.6 Photographs of the samples as function of

time of natural weathering.

3.6. Analysis by Scanning Electron

Microscopy

Analysis of the plasticized samples by scanning

electron microscopy (figure 7) reveals holes at

various locations that are due to the migration

and degradation of additives. In addition, the

obtained results can be explained with the fact

that the area of degradation in PVC consists of

two layers. The surface layer which is subjected

to oxidation grows old because of tear of

macromolecular chains. Below the surface layer

down to some depth, the hydrogen chloride is

eliminated and conjugation polyene chain’s

dominate [37].

FIG.7 Scanning electron microscopy

analysis of the PVC samples containing DOP,

ESO or ESBO after various time of the natural

weathering.

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FIG.8 Scanning electron microscopy analysis of the

PVC samples containing DINA and ESO after

various time of the natural weathering.

4 Conclusions

The results from this study showed a

modification of the mechanical properties after

natural weathering. The results show that chain

scission reactions occurred during the exposure

of the samples to natural weathering;

The FTIR spectra reveals the appearance of a

new bands at 1627 cm-1 and 1667 cm-1 due to

the formation of conjugated double bonds and

appearance of a new band between 3200 and

3500 cm due to hydroxyl compounds (alcohols,

carboxylic acids, hydroperoxides) which are

associated with chain scissions that occurred

during aging of the samples. The absorbance

ratios of the new bands formed during aging

A1627/A1426 and A1654/ A1426 increase in

the case of samples containing DOP, ESBO and

DINA, ESO, which is due to an increase of the

concenration of conjugated double bonds and

thus indicates that the dehydrochlorination of

PVC occurred. This result is confirmed by

Thermogravimetric Analysis (TGA) and

Residual Thermal Stability;

Analysis of the plasticized samples taken after

various time of natural weathering by scanning

electron microscopy reveals holes at various

locations that are due to the migration and

degradation of additives;

Finally, it seems that ESO-based formulations offer

very interesting prospects.

ACKNOWLEDGMENTS

This work was supported by DGRSDT (Direction

Générale de la Recherche Scientifique et du

Développement Technologique, Algeria).

The authors would like to express their gratitude to

Mr Abdekrim Limane from Mouloud Mammeri

University of Tizi Ouzou (Algeria) and Mrs Noura

Arezki from professional formation center of Beni

Douala (TiziOuzou, Algeria) for their help.

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Farid Hamitouche, Nadia Lardjane,

Yves Grohens, Hassiba Habchi Laribi,

Naima Belhaneche Bensemra

E-ISSN: 2224-3496

425

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Contribution of individual authors to the

creation of a scientific article (ghostwriting

policy)

FARID HAMITOUCHE: Carried out the practical

part of this work;

NADIA LARDJANE: Supervised the PhD

student Farid Hamitouche during the realization of

his work and the preparation of the article;

YVES GROHANS: Contributed in the preparation

of the article taking into account these relevant

remarks;

HASSIBA LARIBI-HABCHI: Supervised the PhD

student Farid hamitouche during the realization of

his work;

NAIMA. BELHANECHE-BENSEMRA:

She is the laboratory director; she contributed in the

supervision of the PhD student Farid Hamitouche

and the preparation of the article.

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(Attribution 4.0 International, CC BY 4.0)

This article is published under the terms of the Creative

Commons Attribution License 4.0

https://creativecommons.org/licenses/by/4.0/deed.en_US

WSEAS TRANSACTIONS on ENVIRONMENT and DEVELOPMENT

DOI: 10.37394/232015.2022.18.41

Farid Hamitouche, Nadia Lardjane,

Yves Grohens, Hassiba Habchi Laribi,

Naima Belhaneche Bensemra

E-ISSN: 2224-3496

426

Volume 18, 2022