Research Article

Received: 4 May 2013 Revised: 28 October 2013 Accepted article published: 17 December 2013 Published online in Wiley Online Library:

(wileyonlinelibrary.com) DOI 10.1002/jsfa.6540

HPLC study of migration of terephthalic acid

and isophthalic acid from PET bottles into
edible oils
Amin Mousavi Khaneghah,a∗ Sara Limbo,b Shahram Shoeibic and
Somayeh Mazinanid

Abstract
BACKGROUND: Polyethylene terephthalate (PET) containers for food oil packaging were evaluated with a newly established
determination method for terephthalic acid (TPA) and isophthalic acid (IPA). The analysis of monomers, TPA and IPA that
migrate from PET bottles into oils was performed using high-pressure liquid chromatography with a diode array detector. Three
types of commercial oils (sunflower oil, canola oil and blended oil which included sunflower oil, soy bean oil and cottonseed oil)
were bottled in PET containers. These samples were incubated for 10 days at 49 ◦ C as accelerated test condition.

RESULTS: The means of recovery for this method varied from 70% to 72% and from 101% to 111% for TPA and IPA, respectively.
The results showed that the amounts of specific migration of TPA and IPA into the samples conform to European Union
legislation that identifies specific migration limits. More important, the results highlighted a different behavior of migration as
a function of the fatty acid profile.

CONCLUSION: Previous investigations have been performed with food simulants such as HB307 or 20% ethanol but our study
used real food samples and determined trace amounts of the migrated compounds. Further investigation will be needed to
better explain the influence of fatty acid conformation on migration of PET monomers.


c 2013 Society of Chemical Industry

Keywords: HPLC; isophthalic acid; oils; polyethylene terephthalate; specific migration; terephthalic acid

INTRODUCTION Various substances in plastics used as packaging materials, such

The evaluation of compliance with legislation on all additives,
monomers and starting substances in food contact materials is
an important activity in the food industry. Application of plastics
in food packaging has largely increased during the last decades
because of their availability and the enormous variety of these
materials. In the last few decades, the simple long-chain polymer
polyethylene terephthalate (PET) has become one of the most
common packaging polymers.1,2 PET has now established a strong
base in a number of room-temperature filling and storing food
applications (such as edible oils, some ketchups, peanut butter
and pourable dressings).3 PET is particularly suitable for food
packaging applications because of its chemical inertness. The
three major packaging applications of PET are as containers,
thin oriented films and semi-rigid sheets for thermoforming.4
In addition, incorporation of antioxidant stabilizers into PET
materials increases their application in the food area, particularly
for vegetable oil storage.5
PET is also one of the most promising materials for use as
recycled plastic materials intended to come into contact with
foods after an authorized recycling process. In relation to this,
the Panel on Food Contact Materials, Enzymes, Flavorings and
Processing of the European Food Safety Authority (EFSA) recently
pronounced a positive opinion on the safety of some processes
used to recycle post-consumer PET.
as additives and monomers, but also non-intentionally added
substances coming from the process or the environment, are
of safety concern because they can migrate from the package
into food, and also as a consequence of a consumer misuse.6
Interactions between food and container materials sometimes
occur in trace quantities, and such migration needs to be assessed
to ensure that it is minimal. Compounds that migrate readily
are usually low-molecular-weight and volatile compounds.6 – 8
Nevertheless, it is better that any interaction be absent or
extremely small.2 The term ‘migration’ is used to describe
∗ Correspondence to: Amin Mousavi Khaneghah, Department of Food Science
and Technology, Islamic Azad University, Science and Research Branch, PO Box
1435713715, Tehran, Iran. E-mail: Mousavi.amin@gmail.com
a Department of Food Science and Technology, Islamic Azad University, Science
and Research Branch, Tehran, Iran
b Department of Food Environmental and Nutritional Sciences, Università degli
Studi di Milano, Milan, Italy
c Food and Drug Control Laboratories (FDCLs), Deputy for Food and Drug, MOH,
Tehran, Iran
d Department of Food Science and Technology, Islamic Azad University, Science
and Research Branch, Sabezevar, Iran

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the process of mass transfer from a packaging material to its
contents, in particular when these are liquid or semi-liquid.9
Migration from packaging materials into products generally is
concerned with minor constituents that influence the quality of
the contained product by sensory or toxicological hazards.1,10,11
The toxicity of migrated monomers from PET packaging into
foods has been demonstrated by many investigations: isophthalic
acid (IPA) and terephthalic acid (TPA) are examples of migrant
compounds, and their harmful effects on laboratory animals have
been demonstrated. For this reason, the EFSA fixed levels of
IPA and TPA migration into foods from plastics of 5 and 7.5
mg kg−1 of food, respectively12 – 14 (Regulation 2011/10/EU).
PET is made by polymerizing ethylene glycol with TPA or by
transesterification with dimethyl terephthalate (DMT), commonly
using antimony trioxide as catalyst.1 A more recent development
in PET manufacturing is the modification of polymers by the
incorporation of IPA to generate a polymer. The presence of an
appropriate comonomer such as IPA or DMT slows down the rate
of crystallization, which allows the manufacture of thicker bottle
walls, sheets and films.4 There is also a requirement to extend the
rate of crystallization to restrict movement and deformation at
elevated temperatures, such as for oven-compatible food trays.15
In this case, a nucleating agent or promoter is employed to increase
the polymer’s molecular weight. On the other hand, TPA reacts
with ethylene glycol (EG) at a temperature between 240 and
260 ◦ C and a pressure between 300 and 500 kPa with the use of a
comonomer such as IPA to slow down the rate of crystallization,
thus allowing the manufacture of thicker bottle walls.2
The basic principle of the European Union (EU) legislation
on food contact materials and articles is expounded in the
framework of Regulation 1935/2004/EC, which states that ‘food
contact materials should not transfer to foodstuffs any of their
constituents in quantities that could endanger human health
or cause deterioration in the organoleptic characteristics of
the foodstuff’. This regulation defines the requirements for all
materials intended for food contact applications, and not just for
plastics. Within the framework of this regulation there is a specific
regulation for plastics (2011/10/EC) in which a list of authorized
substances is defined. In this list, monomers commonly used in
making PET and copolyesters for food packaging are established
with a specific migration limit (SML).4 Monomers which can migrate
from PET bottles into foodstuff are TPA, dimethyl terephthalate
(DMT), IPA, dimethyl isophthalate, EG,1,16 diethylene glycol (DEG)
and 1,4-bis(hydroxymethyl) cyclohexane. The principles behind
the regulatory rules followed by other countries are similar to
those of the EU. Migration tests of TPA, IPA and DMT from
PET containers, with food safety in view, have been different
in their basic forms, and analyses based on high-pressure liquid
chromatography (HPLC) have yielded equivocal results.17 – 21
The main purpose of this study was to investigate a new HPLC
diode array detection (DAD) method for determination of specific
migration of TPA and IPA from PET bottles into three different
types of oils (sunflower, canola and blended oil) after storage
under accelerated migration test conditions.
MATERIALS AND METHODS
Reagents and standard solutions
Commercial sunflower, canola and blended oils (containing
sunflower, soy and cottonseed oils) (with added butylated
hydroxytoluene as antioxidant at 100 mg kg−1 in all of the oils)
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packaged in 1 L PET bottles were purchased from Varamin Corp.,
Tehran, Iran.
The PET polymers used had been made by Varamin Corp.,
Tehran, Iran, and consisted of Bottle Grade- PARS PET-BG805
with DEG max content of 2.0%, by wt. Standards of TPA and IPA
were purchased from Fluka Chemical, trademarked Sigma-Aldrich
Corp., Switzerland. HPLC gradient-grade water, acetonitrile, and
methanol (HPLC grade) solvents were purchased from Merck
(Darmstadt, Germany).
Standards and calibration curves
A mixed stock standard solution of 240 ng mL−1 was prepared
from TPA and IPA that were dissolved in methanol and was stored
in the dark at refrigerator temperature (4 ◦ C). Calibration standard
solutions were prepared on the day of use at concentrations of
120, 60, 24, 12 and 6 ng mL−1 and calibration graphs were plotted
using these concentrations of standard solutions.
The detection limit was defined as the concentration
corresponding to a peak height three times the baseline noise
level.
Recovery studies were carried out by spiking selected samples of
oils with the blended standard solution (mix of TPA and IPA) at three
concentrations (240, 750 and 1000 µg kg−1 ). The spiked samples,
as well as the controls, were analyzed in triplicate experiments.
Recovery rates (percent) were calculated by comparing peak area
in the chromatogram with the peak area calculated from the
standard calibration curves.
Fatty acid profiles of the oils
For determination of the fatty acid profile, a transmethylation
technique followed by gas chromatography–flame ionization
detection (GC-FID) determination (AOAC 969.22) was used as
a practical method. The gas chromatograph system (model
6890N, Agilent Technologies, Germany) was equipped with flame
ionization detector and HP88 column (100 m × 250 mm × 0.2 m.
The temperature of the column was from 170 to 190 ◦ C in 5 min
by 0.5 ◦ C min−1 , at which temperature it remained for 20 min; the
detector temperature was 250 ◦ C; the speed of helium as carrier
gas was 0.7 mL min−1 ; the pressure was 10 psı and the volume of
sample injection was 1 µL. Results are expressed as g kg−1 .
Migration testing
Experiments were performed on PET bottles which contained the
three oils (as mentioned above). The oils, which had been stored
in PET bottles at room temperature for about 3 months in the
factory, were poured into glass containers and they passed the
test condition (49 ± 2 ◦ C for 10 days), so they served as blank
samples for each type of oil.
The samples were kept in an incubator at 49 ◦ C for 10 days
to obtain accelerated migration conditions. The temperature was
controlled and the data were recorded by a data logger (LASCAR,
UK). A mixture of methanol (1 mL), chloroform (3 mL) and NaOH
(1 mL) was used for the extraction of migrated monomers from
1 g of oil sample. After centrifugation (Heraeus Biofuge Stratos,
Thermo Scientific, USA) at RCF = 4637 × g and at −3 ◦ C for 20
min, the separated samples were analyzed by HPLC with DAD for
determination of migrants.
HPLC analysis
Standards and the monomers in the samples were separated
and quantified using an HPLC system (model 1200, Agilent
J Sci Food Agric (2014)
Food safety (packaging, migration, oil)
Technologies, Germany) equipped with an Agilent G1311A
quaternary pump and Agilent G1315A diode array detector. The
wavelength used for the detection of monomers was 242 nm. The
column was a Knauer C18 AQ column (250 mm, 5 µm particle
diameter and 4.6 mm internal diameter). The column temperature
was kept at 30 ◦ C using an Agilent G1316A oven. The two mobile
phases used for gradient HPLC elution were (A) H2 O buffered
with 0.1 trifluoroacetic acid/acetonitrile (90:10, v/v) and (B) H2 O
buffered with 0.1 trifluoroacetic acid/acetonitrile (60:40, v/v) with
the following proportions: A–B 90–10, 83–17, 75–25 and 60–40
at 0, 3, 6 and 12 min, respectively. The gradient and elution
conditions employed in this work are shown in Table 1. The flow
rate was 1 mL min−1 and the volume of injection was 10 µL.
Differential scanning calorimetry (DSC) measurements
The melting point temperature and the percentage of crystallinity
were determined for the granules which were used in PET bottle
making. The samples were analyzed by DSC (model DSC822,
Mettler Toledo, USA). According to the temperature program each
sample was heated from 25 to 200 ◦ C with a heating rate of
10 ◦ Cmin−1 and from 200 to 280 ◦ C with a heating rate of 5
◦
C min−1 . The measured heats of fusion were compared with
published values.1,3,22 – 24
Statistical analysis
Experiments on five selected PET bottles containing each type of oil
sample were performed three times. Statistical analysis was done
with SPSS version 11.5 (SPSS Inc., Chicago, IL, USA) and Minitab
version 11.12 (Minitab Inc., State College, PA, USA). The standard
calibration curves were plotted using Excel 2007 (Microsoft, USA).
The significance level was P < 0.05.
RESULTS AND DISCUSSION
The two common monomers from PET plastic packaging are TPA
and IPA Hence simultaneously analysis of these two components
would be of interest.
In general, HPLC chromatograms showed good detection sensi-
tivity. The reproducibility of separation was validated by three indi-
vidual injections of each concentration of standard solution. Quan-
titative parameters of the proposed method, such as linearity range
of detection within the range of 6–120 ng mL−1 , and limit of detec-
tion (LOD) = 6 ng mL−1 based on a signal-to-noise ratio higher than
3, were evaluated. The liner regression equations had determina-
tion coefficients (R2 ) equal to 0.9978 for TPA and 0.9998 for IPA.
TPA recoveries varied in the range of 70–72% for all the tested
oils. Also the mean recoveries for IPA varied in the range of
101–110%.
Figure 1. HPLC chromatogram of blended oil extracted for a real sample.
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Table 1. Result of specific migration of TPA from PET
containers into different types of oil (µg kg−1 )
Type of oil Sample 1 Sample 2 Sample 3 Sample 4
Canola 34.42 ± 0.27a 36.36 ± 0.59a 33.56 ± 0.10 a 37.20 ± 0.11a
Sunflower 21.32 ± 0.20a 23.48 ± 0.24c 22.42 ± 0.21b 23.68 ± 0.15c
Blended 29.83 ± 0.33c 28.65 ± 0.30ab 29.16 ± 0.20b 28.19 ± 0.17a
Values are expressed as mean ± standard deviation (n = 3).
Means in each row with different letters (a, b, c) are significantly different
(P < 0.05) from each other.
Table 2. Result of specific migration of IPA from PET containers into
different types of oil (µg kg−1 )
Type of oil Sample 1 Sample 2 Sample 3 Sample 4
Canola 8.09 ± 0.23bc 7.85 ± 0.10 b 7.22 ± 0.15a 8.26 ± 0.20bc
Sunflower 5.31 ± 0.12a 5.76 ± 0.32ab 6.22 ± 0.12bc 6.48 ± 0.29c
Blended 6.54 ± 0.28a 6.33 ± 0.32a 6.80 ± 0.33a 6.67 ± 0.31a
Values are expressed as mean ± standard deviation (n = 3).
Means in each row with different letters (a, b, c) are significantly
different (P < 0.05) from each other.
An HPLC chromatogram of blended oil extract for a real sample
is shown in Fig. 1. The results obtained from the chromatograms
indicate that the retention times of the two compounds were
between 9 and 11 min and peaks of solvents were eluted in
about 2–4 min. Run time for the analysis of TPA and IPA was
35 min, but all peaks appeared before 12 min, which represents
a short operating time. TPA and IPA in each type of oil in the
partitioned extract were well separated from each other and from
the backgrounds in the spiked oils. The HPLC chromatogram of
the extracted sample in Fig. 1 indicates that the extraction solvent
did not critically interfere with the detection of the monomers.
Samples without treatment were stored by maintaining the oil
bottles from production until time of purchase (about 3 month)
at room temperature (25 ◦ C with relative humidity about 65%);
probably, a slight migration of monomers occurred which could
not be measured by common methods.
Amounts of the specific migration from PET bottles into the
different types of oils are shown in Tables 1 and 2. The highest
levels of migration were 37.20 ± 0.11 µg kg−1 and 8.26 ± 0.20 µg
kg−1 for TPA and IPA, respectively, in canola oil samples. The lowest
levels of migration were 21.32 ± 0.20 µg kg−1 and 5.31 ± 0.12 µg
kg−1 for TPA and IPA, respectively, in sunflower oil samples.
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Begley and Hollifield17 studied the migration of monomers into
olive oil by microwave heating. They stored the PET films and
bottles containing 1.5 and 1.7 µg kg−1 of terephthalic acid with
food simulants (3% acetic acid and 15% ethanol) at 40 ◦ C for 10
days. They used an HPLC method with a LOD equal to 0.4 µg
mL−1 . There was no evidence of migration.17 Lee reported that
EG and TPA could be detected but not any other monomers.21
They found contents from 0.32 to 1.23 mg kg−1 and from 0.51
to 13.64 mg kg−1 when testing for EG and TPA, respectively.
However, in the same report it was mentioned that no measurable
quantities of migrated PET monomers were found in the food-
simulating solvents. Park et al. reported that no migration was
detected from 56 PET containers that had been in contact with
four food simulants (water, 4% acetic acid, 20% alcohol, and
n-heptane) under different conditions.2 They used HPLC with
a single-wavelength UV detector for determining the possible
migrated compounds. With the selected method the LOD was 0.1
µg mL−1 . Farhodi et al. studied the migration of di-(2-ethylhexyl)
phthalate from PET bottles used in dough (yogurt diluted with
water) by 3% acetic acid as simulant and they showed that the
amount of the migrated compound was within the migration limit
regulations of the EU. The results of our study showed that the
amounts of migration of TPA and IPA in the samples conformed
to the EU SML. In fact, the EU established SMLs for TPA and IPA of
7.5 and 5 mg kg−1 , respectively. In our study migration of TPA and
IPA were lower than the established limits set by the EU.
Another consideration concerns the relationship between the
migration behavior and oil composition in terms of acidic profile.
The fatty composition of the oils is listed below:
• sunflower oil: palmitic acid 75.5 (g kg−1 ), oleic acid 233.7 (g
kg−1 ) and linoleic acid 617.6 (g kg−1 );
• canola oil: palmitic acid 50.7 (g kg−1 ), oleic acid 560.1 (g kg−1 )
and linoleic acid 209.4 (g kg−1 );
• blended oil: palmitic acid 94.3 (g kg−1 ), oleic acid 238.0 (g kg−1 )
and linoleic acid 580.0 (g kg−1 ).
According to the migration data in Tables 1 and 2, the highest
levels of migrated TPA and IPA into oils were found in canola oil, in
which the oleic acid content was more than double with respect to
sunflower and blended oils. This fact suggests a strong effect of the
type of fatty acid on PET monomer migration. Probably, the olefinic
conformation of cis-monounsaturated fatty acids influences the
chain packing and the chain–chain interactions in such a way that
diffusion of the monomers could be facilitated. The reason of this
correlation between amount of migration and fatty acids profile
might be explained by future research.
Characteristics of the PET samples obtained by the DSC test
are shown in Table 3. The initial (onset) and end temperatures of
melting (termination), and also the melting point (peak) showed
lower values in comparison with other investigations (Table 3).
According to these data, the percentage of crystallinity was lower
than mentioned in published references and the direct effect of
decreasing crystallinity on the increasing migration phenomenon
has to be further tested. Consequently, the extent of the specific
migration of monomers is rather high in comparison with previous
investigations done by others.1,3,22 – 24
CONCLUSION
This study was undertaken to quantify the migration of the harmful
compounds TPA and IPA into three different edible oils (canola,
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Table 3. Characteristics of PET samples obtained by the DSC test
Type of Onset Termination Melting point
materials (◦ C) (◦ C) (peak) (◦ C)
H (mW ◦ C)
Granules 233.23 241.95 236.75 −62.56
Milled granules 231.42 240.68 236.33 −54.22
sunflower and blended oils) by means of an HPLC–DAD system.
The migration was related to the fatty acid composition of the
oil: if the concentration of monounsaturated acid was high, the
migration of TPA and IPA was high too. Previous investigations
have been performed with food simulants such as HB307 or 20%
ethanol,25 and the results showed that there was no evidence of
migration. Our study used real food samples and determined trace
amounts of the migrated compounds. The amounts of migrated
monomers from PET packaging into the oils were below the limit
specified by EU legislation for TPA (7.5 mg kg−1 ) and for IPA (5
mg kg−1 ), so the PET containers can be considered in compliance
with the EC Regulation. The conditions used in the accelerated
test (49 ± 2 ◦ C for 10 days) were similar to the FDA protocol, but in
actual conditions, and especially in tropical regions, the conditions
of storage for oil products packed in PET bottles may be more
severe, so it is necessary to control and improve the distribution
chains and the conditions of storage to guarantee product safety.
Further investigation will be needed to better explain the
influence of fatty acid conformation on migration of PET
monomers.
ACKNOWLEDGMENT
The authors are grateful to the staff of Packaging and Toxicology
Labs, Food and Drug Control Labs, for their helpful cooperation
during this project.
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