Synthesis, Characterization, and Applications of Anticorrosion Polyurethane Coating: The Effect of Bisphenol F
Corresponding email: gulzhakh@yandex.ru
Published at : 18 Sep 2024
Volume : IJtech
Vol 15, No 5 (2024)
DOI : https://doi.org/10.14716/ijtech.v15i5.7022
Yeligbayeva, G., Moldabayeva, G.Z., Azzam, K.M.A., Bekbayeva, L., Negim, E-.S., Shalash, M., Usman, A., 2024. Synthesis, Characterization, and Applications of Anticorrosion Polyurethane Coating: The Effect of Bisphenol F. International Journal of Technology. Volume 15(5), pp. 1258-1270
| Gulzhakhan Yeligbayeva | School of Petroleum Engineering, Satbayev University, 22 Satpayev Street, Almaty 050013, Kazakhstan |
| Gulnaz Zh. Moldabayeva | School of Petroleum Engineering, Satbayev University, 22 Satpayev Street, Almaty 050013, Kazakhstan |
| Khaldun M Al Azzam | Department of Chemistry, Faculty of Science, The University of Jordan, 11942 Amman, Jordan |
| Lyazzat Bekbayeva | National Nanotechnology Open Laboratory, Al-Faraby Kazakh National University, Almaty, Kazakhstan |
| El-Sayed Negim | 1. School of Petroleum Engineering, Satbayev University, 22 Satpayev Street, Almaty 050013, Kazakhstan 2. School of Materials Science and Green Technologies, Kazakh-British Technical University, St. |
| Marwan Shalash | Faculty of Pharmacy, Zarqa University, Zarqa 13110, Jordan |
| Anwar Usman | Department of Chemistry, Faculty of Science, Universiti Brunei Darussalam, Jalan Tungku Link, Gadong BE1410, Negara Brunei Darussalam |
Polyurethane
coatings were synthesized through polyaddition polymerization using various
polyols. These polyols included polypropylene glycol with different molecular
weights, such as PPG-2000, and PPG-1200, as well as 1,4- butanediol.
Additionally different contents of bisphenol F; namely 4.5, 11.5, and 24.2%, as
well as methylene diphenyl diisocyanate at an NCO/OH ratio of 2.0. The
prepolymer polyurethane films were analyzed to study their characteristics
using techniques such as Fourier transform infrared spectroscopy, viscosity measurements,
thixotropic index analysis, and mechanical property evaluations. The pot life
and dry times of polyurethane coating containing 11.5% bisphenol F were 90
minutes and 10 hours (time to touch), respectively, with full hardening
achieved at 28 hours. Furthermore, the coating exhibited excellent mechanical
properties: tensile strength of 80 N/m², elongation of 260%, adhesion strength
of 10 MPa (cross-hatch), hardness of 95, and a contact angle of 118°. These
properties, coupled with its strong adhesion (10 MPa) to metal surfaces,
contributed to its outstanding chemical and corrosion resistance. The coatings
obtained from the prepolymer polyurethane based on 11.5% bisphenol F exhibited
the highest mechanical properties and water, chemical, and corrosion resistance
followed by 4.5%, and 24.2%, respectively.
Bisphenol F; Coating; Corrosion; Polyurethane; Resistance
Currently, corrosion of metallic buildings is a major
global issue, and reducing corrosion losses has become one of the most
significant challenges in industrialized countries since these losses are
expected to be extremely costly. One of the most effective corrosion prevention
strategies is to protect metals using paint and polymer coatings, which have
been used effectively for many years and are still being utilized for
anticorrosion protection of metallic structures (Petrunin,
2022). Metal materials are commonly utilized for
However, it is well known that the
strength and durability of adhesion bonds at the metal/polymer interface play
an important role in determining the protective qualities of polymer coatings.
As a result, another major science and technology goal is the development of
ways to increase the adhesive properties of protective covering (Petrunin et al., 2021).
Polymers
are widely used for their superior mechanical qualities, resistance to organic
and inorganic solvents, and corrosion resistance (Arrieta,
Barrera, and Mendoza, 2022; Bekbayeva et al., 2022; Sun, You, and Teo, 2022).
Polyurethane prepolymers (PUAs) are widely used in different industrial
applications including coating, paint, waterproofing, concrete, anticorrosion,
and wear resistance (Kaur et al., 2022;
Patil et al., 2021; Negim et al., 2020; Xiang et al.,
2020; Alam et al., 2014; Tathe and Jagtap, 2014; Chaudhari et al.,
2013; Petrovic et al., 2013; Akintayo, Akintayo, and Ziegler, 2011).
The latter is attributed to its excellent mechanical characteristics,
weatherability, corrosion resistance, and adhesion (Liu
et al., 2021).
A
number of researchers have investigated different designs for the polyurethane
backbone based on the polymerization process, polyols, and isocyanates to
achieve high-performance anticorrosion coatings and good mechanical properties (Das and Mahanwar, 2020; Zhang, Tu, and Dai, 2012).
PUAs are formed through the polyaddition of polyols and isocyanates. Polyols
are crucial for enhancing adhesion strength and flexibility in coatings,
whereas isocyanates contribute significantly to improving their mechanical properties (Negim et al., 2020; Akindoyo et al., 2016;
Alagi et al., 2016). Furthermore, PUAs with urethane linkages
exhibit improved adhesion, abrasion resistance, hardness, and corrosion
resistance (Akindoyo et al., 2016).
Additionally, the polyol ratio can affect the surface smoothness, contact
angle, and crystallinity of PUAs (Negim et al., 2020) are different kinds of isocyanates are
classified into aliphatic and aromatic isocyanates. However, PUAs prepared from
aromatic isocyanates are more rigid and less expensive than those prepared from
aliphatic isocyanates (Negim et al., 2024;
Asriyanti et al., 2022; Xu et al., 2012).
Literature
review reveals that Ismail, Motawie, and Sadek, (2011)
prepared a polyurethane coating using polyols derived from soybean oil,
glycerol, and phthalic anhydride at ratios of 20%, 40%, and 60%, respectively.
Diphenylmethane diisocyanate was also used in the preparation process. The
findings demonstrated an improvement in the coatings' mechanical, physical, and
chemical qualities as well as their anticorrosive qualities (Serekpayeva et al., 2022). Tayde, Thorat, and Sonawane (2017) and Harjono, Sugita, and Mas’ud (2012) demonstrated that castor oil
or jatropha oil could be developed as a raw material for polyurethane coatings,
respectively. This behavior is associated with improved film strength and
higher resistance to chemicals due to the higher hydroxy content in the castor
oil as well as higher crosslinking density. However, a lower hydroxyl content
results in greater film elasticity. By using polyols prepared from castor oil
and ethanol amine in the preparation of the prepolymer polyurethane, Patil (2019) showed that polyurethane coatings have
a long-term protective effect on metal corrosion. On the other hand, bisphenol
A (Figure 1) is utilized as a chain extender for the production of polyurethane
due to its high oxidation stability, and the two side methyl groups of
bisphenol A hinder the crystallization of the hard segments (Xiang et al., 2020).
Figure 1 Chemical Structure of Bisphenol
A
The
hyperbranched polyester polyols used for polyurethane coating provide excellent
mechanical strength, chemical resistance, and thermal stability (Abdollahi and Khalili, 2024; Patil, 2018; Elsaid, Badr,
and Selim, 2013). In a study by Patil (2019),
it was demonstrated that polyurethane coatings based on polyol derived from
castor oil and diethanol amine provide long-lasting corrosion protection for
metal surfaces in the preparation of prepolymer polyurethanes. On the other
hand, bisphenol A used as a chain extender for the production of polyurethane
due to the high oxidation stability, and two side methyl groups of bisphenol A
hinder the crystallization of the hard segments (Xiang
et al., 2020). The hyper-branched polyester polyols for
polyurethane coating provide excellent mechanical strength, chemical
resistance, and thermal stability (Abdollahi and
Khalili, 2024).
This work investigates the development of prepolymer polyurethane coatings by reacting to four different polyols namely, PPG-2000, PPG-1200, and 1,4- butanediol, with different contents of bisphenol F and diphenylmethane diisocyanate (aromatic polyisocyanate) at NCO/OH ratio of 2. The obtained prepolymer polyurethane was characterized by FTIR and physicomechanical tests. The prepolymer polyurethane coatings were applied to mild steel panels and cured at room temperature. The pot life, hardness, impact resistance, flexibility, mechanical properties, adhesion properties, and chemical/corrosion resistance were investigated and measured utilizing standard methods.
Polypropylene
glycol (PPG, Mw = 2000 g/mol, OH number = 56 mg KOH/g, Korea
PTG, Korea), polypropylene glycol (PPG, Mw = 1200 g/mol, OH
number = 98 mg KOH /g, Korea PTG, Korea), and 1,4 butanediol (1,4-BD, Mw
= 90,12 g/mol, OH number = 1245 KOH mg/g, Sigma) were dried and degassed at 80oC,
and 1-2 mm Hg for 2 h before use. Dibutyltin dilaurate (DBTDL, Fluka),
diphenylmethane diisocyanate (MDI, Bayer AG), bisphenol F (BPF, Sigma), NaCl
(10%), NaOH (1 M), HCl (1 M), H2SO4 (1 M) and HNO3
(1 M) were obtained from Aldrich (St. Louis, MO, USA). Acetone, xylene,
toluene, benzene, butanol, isopropyl alcohol, chloroform, and cyclohexane were
obtained from Fluka (Charlotte, NC, USA). The titanium dioxide pigment used was
Tiona-595 (crystal, KSA), the rheological and anti-setting used was SR882 and
bntone 27 (Elementis, Malaysia), and the dispersing agent was Troysperse CD1
(Troy Co., Canada).
2.2. Synthesis of the
prepolymer polyurethane (PUA)
A 500 mL
round-bottom, with a three-necked separable flask with a thermometer, condenser
with a drying tube, and a mechanical stirrer was filled with polyols, including
PPG-2000, PPG-1200, and 1,4 butanediol (1,4-BD). In an oil bath maintained at a
constant temperature, the reaction was conducted in an N2
atmosphere. The diphenylmethane diisocyanate (MDI) was transferred to the
flask, and then the mixture was heated at 95oC for 1 h. Next,
bisphenol F (BPF) was added to the mixture, and the di-n-butylamine titration
technique (ASTM D 2572) was used to calculate the theoretical NCO value (ASTM, 2019).
The reaction then continued at the same temperature, and the samples formed a
viscous prepolymer. Figure 2 illustrates the chemical method used to prepare
the prepolymer, while Table 1 displays the preparation of samples with various
BPF amounts and constant NCO/OH ratio.
Table 1 Feed
compositions of the prepolymer polyurethane (PUA) with different contents of
polyols
|
PUA1 |
PUA2 |
PUA3 |
PUA4 |
|||||
|
|
Wt
(g) |
Wt
(%) |
Wt
(g) |
Wt
(%) |
Wt
(g) |
Wt
(%) |
Wt
(g) |
Wt
(%) |
|
Polyols,
OH |
||||||||
|
PPG-2000 |
12.8 |
23.2 |
12.8 |
28.5 |
12.8 |
36.6 |
12.8 |
51.4 |
|
PPG-1200 |
38.31 |
69.9 |
26.3 |
58.7 |
14.31 |
41.2 |
2.31 |
9.3 |
|
1,4 BD |
3.7 |
6.9 |
3.7 |
8.3 |
3.7 |
10.7 |
3.7 |
15.1 |
|
BPF |
0.0 |
0.0 |
2.01 |
4.5 |
4.0 |
11.5 |
6 |
24.2 |
|
Total |
54.81 |
100 |
44.81 |
100 |
34.81 |
100 |
24.81 |
100 |
|
Mole
of OH (gm/mole) |
0.0798 |
0.0798 |
0.0798 |
0.0798 |
||||
|
Isocyanate,
NCO |
||||||||
|
MDI |
39.9 |
39.9 |
39.9 |
|
39.9 |
|
||
|
Mole of NCO (gm/mole) |
0.1596 |
0.1596 |
0.1596 |
|
0.1596 |
|
||
|
NCO/OH |
2 |
2 |
2 |
|
2 |
|
||
Figure 2 The formation
of the prepolymer polyurethane (PUA). Please refer to section 2.2 for the
conditions used
2.3. Preparation of
polyurethane coatings (PUAC)
Figure 3 The
preparation of the polyurethane coatings (PUAC). Please refer to section 2.3
for the conditions used
Table 2 Anti-corrosion polyurethane coating (PUAC)
formulations
|
Raw materials |
Weight
percent |
|
Prepolymer PUA |
35 |
|
Rheological agent |
0.5 |
|
Titanium dioxide |
30 |
|
Anti-setting additive |
1.5 |
|
Dispersion agent |
0.03 |
|
Pigment |
10.22 |
|
Xylene |
15 |
|
Butanol |
6 |
|
Dibutyltin dilaurate
(DBTDL) |
1.75 |
2.4.
Film coating preparation
The coating samples
polyurethane coatings (PUAC) were applied to mild steel panels (70 mm × 200 mm)
according to ASTM D4147-93 and allowed to dry at ambient temperature for 7
days. For further analysis and measurement, the films were kept at room
temperature in a desiccator. The thickness of the samples ranged from 70
to 75 mm in the day case and from 80 to 90 mm in the wet
case according to Sheen – Ecotest Plus B FN2, type 121-17-00.
2.5. Characterization
The obtained PUA was
characterized by ALPHA Fourier transform infrared (FTIR) spectroscopy,
(Bruker). FTIR spectroscopy was used to identify the functional groups of PUA
(in liquid form). The viscosity (cps) of the epoxy resins and reactive dilutes
were measured at room temperature utilizing a Brookfield viscometer according
to ISO 12058-1 at speeds of 5 and 50 rpm (in liquid form).
The MTS 10/M
tensile testing equipment was used to quantify the tensile characteristics of
the PUA and PUAC films, at a crosshead speed of 50 mm/min. A 1-kN load cell was
utilized, and an average of at least four measurements was obtained. A CAHN
DCA-322 analyzer running at 25 °C with a water drop at a velocity of 100 lm/s
was used to quantify the contact angle that developed between the water
droplets and the sample's surface. To evaluate a product's resistance to
cracking and/or detachment from a metal substrate after it has been bent around
a cylindrical mandrel under typical circumstances, a cylindrical mandrel tester
(ASTM D522, 2001) was performed. A tubular impact tester (ASTM D2794, 2019) was
used to determine the impact resistance of the film, and an economic cross
hatch tester (ASTM D3359, 2001) was used to evaluate the adhesion of the used
coatings. For the adhesion strength measurements of the PUA and PUAC, pull-out
tests were conducted according to standard methods (En,1542, 1999). The corrosion
resistance of the coated panels was tested by salt (10% NaCl), base (1.0 M
NaOH), and acid (1.0 M HCl) addition, and a solvent resistance test (ASTM
D5402-93) and a water resistance test (D1647-89) were also conducted. During
each test, the samples were submerged in their respective solutions for a
duration of one week. The purpose of this procedure was to evaluate the
corrosion resistance, solvent resistance, and water resistance of the samples.
The dry times of the samples were also recorded, and this was done at an
ambient temperature of 25oC.
3.1. Fourier transform infrared (FTIR) spectrometer
analysis
Figure 4 FTIR spectrum of the prepolymer polyurethane
(PUA)
3.2. Viscosity
Figure 5 Viscosity and
TI of prepolymer polyurethane as a function of BPF
3.3.
Mechanical Properties
Table
3 shows that the tensile strength of the prepolymer polyurethane increased as
the content of BPF increased from 4.5% to 11.5%, while after 11.5%, the tensile
strength decreased. The prepolymer polyurethane, which contained 11.5%
bisphenol F (PUA3), demonstrated the highest tensile strength of 78.1 MPa. On
the other hand, PUA4 displayed the lowest tensile strength of 29.5 MPa.
Notably, these values are higher than the tensile strength obtained from the
polyurethane prepolymer that was modified with epoxy and 1,3-propanediol, as
reported by (Lutviasari et al., 2017).
However, PUA4 had greater elongation at break (140%) than PUA3 (125%), PUA2
(108%) and PUA1 (103%). The effect of BPF content on the hardness and contact
angle of the prepolymer polyurethane is presented in Table 1. The contact angle
increased as the content of BPF increased from 4.5% to 24.2% while the hardness
increased as the content of BPF increased from 4.5% to 11.5%. PUA4 had the
highest contact angle (140) and lowest hardness (55), while PUA3 had the
highest hardness (98) and PUA1 had the lowest contact angle (103) as in the
study reported by authors (Negim et al.,
2024). The decrease in the mechanical properties of the prepolymer is
attributed to the increase in the number of soft segments in the prepolymer
polyurethane upon increasing the BPF content to 24.2% (Rahman
et al., 2013).
Table 3 Mechanical
properties of the prepolymer polyurethane cast films
|
|
PUA1 |
PUA2 |
PUA3 |
PUA4 |
|
Tensile strength (MPa) |
32.7 |
45.9 |
78.1 |
29.5 |
|
Elongation (%) |
170 |
85 |
35 |
25 |
|
Hardness (shore A) |
65 |
73 |
98 |
55 |
|
Contact angle |
103 |
108 |
125 |
140 |
Keynotes to abbreviations: PUA1 = prepolymer
polyurethane containing 0.0% bisphenol F, PUA2 = prepolymer polyurethane
containing 4.5% bisphenol F, PUA3 = prepolymer polyurethane containing 11.5%
bisphenol F, and PUA4 = prepolymer polyurethane containing 24.2% bisphenol F
3.4.
Coating properties
3.4.1. Drying time and mechanical properties
Table 4 illustrates how the BPF concentration affects the polyurethane coating's drying and mechanical characteristics. The pot life and dry time of polyurethane coating containing 0.0% bisphenol F (PUAC1) were 90 minutes, 10 h (set to touch), and 28 h (dry hard), while the pot life and dry time of the coating decreased with increasing BPF content from 4.5% to 11.5%.
However, the highest content of BPF (24.2%) was associated with the longest pot life and dry time than polyurethane coating based on castor oil (Tayde, Thorat, and Sonawane, 2017) and shorter than polyurethane coating made from soybean oil (Ismail, Motawie, and Sadek, 2011).
Moreover, the BPF content increased from 4.5% to 11.5%, leading to an improvement in the mechanical characteristics of the polyurethane coating, such as tensile strength, elongation at break, adhesion hardness, flexibility, and contact angle. The polyurethane coating, which contains 11.5% bisphenol F (PUAC3), exhibited superior mechanical properties compared to the polyurethane coatings with 24.2% bisphenol F (PUAC4), 4.5% bisphenol F (PUAC2), and 0.0% bisphenol F (PUAC1). The increase in the mechanical properties is due to the rigidity of the soft segment from BPF and the hydrogen bonding between the N–H and C=O groups (Negim et al., 2011). Generally, different factors affect the mechanical properties of coatings, including the type of polyurethane, the presence of polyols, the reaction process, and other additives (Kant et al., 2024). The interaction between the polarity of the benzene ring in the BPF and the polarity of the urethane groups resulted in greater adhesion strength in PUAC2, PUAC3, and PUAC4 than in PUAC1. PUAC3 exhibited the highest adhesion (10 MPa), while PUAC1 exhibited the lowest adhesion (6 MPa) which is higher than obtained by the authors (Tayde, Thorat, and Sonawane, 2017; Rahman et al., 2013). However, 100% of all the samples passed the adhesion test (crosshatch). The polyurethane coating films had hydrophobic properties, as indicated by a contact angle greater than 90o (Ma et al., 2023; Rahman et al., 2013). The coating films showed good flexibility according to the conical-Mandrel test. This is attributed to the 100% adhesion of all the coating films to the surface, as indicated by the adhesion (pall-off test) and cross-hatching (George, Suraj, and Thomas, 2023). In addition, all the samples had an impact resistance of 1 kg at a height of 1 m, which was accredited to the good adhesion of the coating on the surface of the metal (Mayer, Dmitruk, and Pach, 2018).
3.4.2.
Chemical and corrosion resistances
Polyurethane
polymers were prepared by polyaddition polymerization, using various polyols
such as PPG-2000 and PPG-1200, along with different amounts of bisphenol F
(4.5%, 11.5%, and 24.2%), and diphenylmethane diisocyanate. The NCO/OH ratio
used for the polymerization process was 2.0. The obtained polyurethane
prepolymers based on 11.5% bisphenol F
as a polyol exhibited better physical and mechanical properties than did
4.5% and 24.2% bisphenol F because of the hydrogen bonds resulting from
interactions that contributed to
the dipolar nature of the benzene rings from bisphenol F and diphenylmethane
diisocyanate as well as between C=O and N–H. Furthermore, a polyurethane
coating with an 11.5% bisphenol F content, based on prepolymer polyurethane,
demonstrated outstanding mechanical properties, as well as excellent chemical
and corrosion resistance. This can be attributed to the coating's exceptional
adhesion (10 MPa) to the metal surface. Future studies should focus on understanding
the durability of Bisphenol F-containing anticorrosion polyurethane (PU)
coatings, investigating their long-term stability under various environmental
conditions, examining the mechanisms of aging and deterioration, and exploring
the development of eco-friendly, sustainable PU coatings using bio-based raw
ingredients. The future study aims to explore the
recycling and reusing of PU coatings with Bisphenol F to promote sustainability
and reduce environmental impact. It also assesses the toxicity and
environmental impact of these coatings to ensure they meet safety standards and
regulations. Future research can enhance their performance, expand their use in
anticorrosion and high-performance coatings.
This research was carried out with the financial support of the Science
Committee of the Ministry of Science and Higher Education of the Republic of
Kazakhstan (BR21881822 Development of technological solutions for optimizing
geological and technical operations when drilling wells and oil production at
the late stage of field exploitation, 2023–2025).
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