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Rapeseed oil gallate-amide-urethane coating material: Synthesis and evaluation of coating properties

  • Manawwer Alam EMAIL logo , Mohammad Altaf and Naushad Ahmad
Published/Copyright: February 15, 2022
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e-Polymers
From the journal e-Polymers Volume 22 Issue 1

Abstract

The present manuscript describes the synthesis of urethane (ROGAU) coating material from Rapeseed oil (RO), Gallic acid (GA) and Toluylene-2,4-diisocyanate [TDI], for the first time. The reaction was accomplished in the following steps: (i) amidation of RO, producing diol fatty amide, HERA, followed by (ii) gallation reaction of HERA with GA, resulting in RO-based gallate amide (ROGA). The structural elucidation by FTIR and NMR confirmed the insertion of amide and ester moieties in the ROGA backbone. To add applicational value to ROGA, it was then derivatized by urethanation reaction with TDI to develop ambient temperature-cured ROGAU, as a corrosion protective coating material. ROGAU coatings were scratch resistant, well-adherent, and flexible to a considerable extent and showed good corrosion resistance performance toward saline medium (3.5 wt% NaCl). ROGAU coatings can be safely used up to 200°C.

Keywords: rapeseed oil; gallic acid; polyurethane; coatings

1 Introduction

The environmental concerns, fast depleting petroleum resources, and high costs of petro-based chemicals have led to the growing interests in polymeric resins derived from sustainable resources such as starch, cellulose, chitosan, cashewnut shell liquid, and others. Natural polymers are advantageous as they are biodegradable, renewable, biocompatible, eco-friendly, and cost-effective (1,2,3). Vegetable oil (VO)-based resins (epoxies, polyols, polyurethanes, polyesteramides) have attracted great attention as VO are cost effective, easily available, and eco-friendly (4,5,6). VO-based polyesteramide resins (PEAs) contain amide, ester, and long fatty alkyl chains in their backbone. They have been obtained from several VOs such as linseed, soybean, castor, Pongamia glabra, Jatropha, Musea ferrea, and many others by first transforming these VO into their respective fatty amide diols, followed by esterification reaction of the obtained fatty amide diols with maleic anhydride, phthalic anhydride, tartaric acid, citric acid, succinic acid, malonic acid, and others (4,7,8).

Rapeseed oil (RO) is produced in China, Canada, Ukraine, Australia, and India (9). It comprises the following fatty acids: oleic (64.5%), linoleic (18.3%), linolenic (6.8%), gadoleic (1.3%), and erucic (0.8%) along with other saturated fatty acids (10). RO has been transformed into alkyd, epoxies, polyols, and polyurethanes by chemical transformations (10,11,12,13). Interestingly, no research work has yet been reported on the synthesis of RO-based gallate amide and polyurethane therefrom, although RO has functional attributes for the same.

Gallic acid (GA), 3,4,5 trihydroxy benzoic acid, is a phenolic acid, a plant-derived flavonoid, and exhibits anti-inflammatory effects, antibacterial activities, and wound healing efficiency (14,15,16). Found in gallnuts, tea leaves, oak bark, and other plants, it is used in pharmaceutical industry, inks and dyes, photography, and paper industry. GA has been used to prepare bio-based epoxy resin by glycidylation of GA through allylation followed by epoxidation and also as a curing agent of epoxy resin (17,18,19). Epoxidized GA was then treated with amine curing agents, and the performance was compared with that of commercial epoxy resin by Tarzia et al. (18). Ma et al. synthesized GA-based curing agent, with the plurality of double bonds, which served as a curing agent for acrylated soybean oil coatings (14). Karaseva et al. prepared GA-based epoxy resin reinforced with carbon nanotubes with good thermal stability relative to pure epoxy resin (19). Patel et al. have used GA-derived flame-retardant crosslinking agent for polyurethane (PU) coatings (20).

PU forms homogenous and well-adherent coatings and acts as a protective sheath dissuading the contact of the metal substrate with corrosive ions. PU coatings contain heteroatoms, oxygen, and nitrogen, in their backbone, that interact with d-orbitals (vacant) of metal forming co-ordinate bonds, thus enabling corrosion protections against corrodents through barrier action (21,22). Thus, the introduction of gallate and urethane in VO coatings is expected to be feasible for corrosion protection. Although GA has been used as a curing and crosslinking agent, literature reports on the use of GA as a raw material for the development of corrosion protective coatings are not available to the best of our knowledge. In previous works, GA has been used as a “green corrosion inhibitor” (23,24). This article presents the preparation of RO-based gallate amide urethane (ROGAU) using RO and GA for the first time by three steps: (i) base catalyzed amidation of RO rendering HERA diol, (ii) gallation of HERA diol, producing ROGA, and (iii) ROGA was further treated with TDI forming urethane, ROGAU. ROGAU yielded ambient cured corrosion protective coatings, which were tested by standard methods as presented in this article. The aim of this study is to introduce gallate and urethane moieties in RO backbone and study their effect on structure, morphology, physico-mechanical performance, hydrophobicity, and corrosion resistance of coatings.

2 Experimental

2.1 Materials

Rape seed oil (RO), diethanolamine, sodium metal, sodium chloride (Winlab Limited, Berkshire, UK), GA (J.T. Baker Chemical Co. Phillipsburg, New Jersey, USA), toluene 2–4 diisocyanate (TDI) (80% tech, Acros Organics, New Jersey, USA), and toluene (BDH Chemicals Ltd. Poole, England) were obtained.

2.2 Synthesis of N,N-bis(2-hydroxyethyl) RO fatty amide (HERA)

HERA was prepared according to our previously published articles (25,39).

2.3 Synthesis of RO-based gallate-amide (ROGA)

HERA (1 mol) was placed in a four-necked flat-bottomed conical flask equipped with a nitrogen inlet tube and a thermometer. The temperature of the magnetic stirrer was maintained at 50°C, and GA (1 mol) was added in small amounts to the flask containing HERA. The contents were mixed thoroughly, and then the temperature was further increased to 150°C and thus maintained for 5 h. The reaction was monitored by recording FTIR spectra and acid value (AV) determination at regular intervals of time. The desired low AV and appearance of characteristic absorption bands in the FTIR spectrum confirmed the formation of ROGA.

2.4 Synthesis of RO-based gallate-amide-urethane (ROGAU)

TDI was added to the cooled flask containing ROGA (30%, 35%, 40%, and 45% w/w on the weight of HERA) dropwise under continuous stirring, and after adding TDI, the reaction temperature was increased up to 60°C. The urethanation reaction was closely monitored by recording FTIR spectra at regular intervals. The reaction was continued at this temperature until the FTIR spectrum indicated the formation of urethane.

2.5 Characterization

2.5.1 Structural elucidation and morphology analysis

The structural elucidation and morphology analysis of the synthesized material were performed by the following methods:

  1. Fourier transformation infrared spectroscopy (FTIR): FTIR spectrophotometer (Spectrum 100, Perkin Elmer Cetus Instrument, Norwalk, CT, USA).

  2. Nuclear magnetic resonance (NMR): 1H NMR and 13C-NMR (JEOL DPX400MHz, Japan) using deuterated chloroform (CDCl3) and dimethyl sulfoxide (DMSO) as solvents and tetramethylsilane (TMS) as an internal standard.

  3. Thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC): TGA and DSC (Mettler Toledo AG, Analytical CH-8603, Schwerzenbach, Switzerland) were performed to study the thermal stability of ROGA and ROGAU.

  4. Field-emission scanning electron microscopy: FE SEM, JSM 7600F, JEOL, Japan.

  5. Energy-dispersive X-ray spectroscopy: EDX, Oxford, UK. Acid value: AV (ASTM D555-61).

2.5.2 Preparation of coatings and their performance evaluation

Carbon steel (CS) strips (composition (Fe, 99.51%; Mn, 0.34%; C, 0.10%; P, 0.05%) of standard sizes (70 mm × 25 mm × 1 mm and 25 mm × 25 mm × 1 mm) were prepared by polishing with different grades of silicon carbide paper, washing with double distilled water, and degreasing with methanol and acetone, followed by drying at room temperature.

ROGAU (40% solutions in toluene, w/v) was applied by brush on clean CS panels. The coated panels were left undisturbed to dry at room temperature for 2 weeks. The curing reaction/drying of coatings was monitored by recording FTIR spectra at regular intervals of time, and the dried panels were then subjected to the following tests by standard methods.

2.5.3 Physico-mechanical

Thickness measurements (ASTM D 1186-B), scratch hardness (BS 3900), crosshatch (ASTM D3359-02), pencil hardness test (ASTM D3363-05), impact test (IS:101 (Part 5/Sec-1)-1988), flexibility/bending test (ASTM D3281-84), gloss (Gloss meter, Model: KSJ MG6-F1, KSJ Photoelectrical Instruments Co., Ltd Quanzhou, China), and contact angle measurements (CAM200 Attention goniometer) were performed by standard methods.

Corrosion resistance: Test specimens were attended as a working electrode. An exposed surface area of 1.0 cm2 was fixed by PortHoles electrochemical sample mask, with Pt electrode as counter electrode and 3 M KCl-filled Ag electrode as a reference electrode (Auto lab Potentiostat/galvanostat, PGSTAT204-FRA32, with NOVA 2.1 software; Metrohom Autolab B.V. Kanaalweg 29-G, 3526 KM, Utrecht, Switzerland).

3 Results and discussions

RO was derivatized into fatty amide diol by base-catalyzed amidation reaction forming HERA (Scheme 1). HERA has one amide, two hydroxyl groups, and an alkyl chain; GA has three hydroxyl groups, a benzene ring, and a carboxylic acid group. HERA was esterified with GA-producing ROGA (Scheme 2). The synthesis of ROGA was carried out without any solvent. The free hydroxyl groups of ROGA were treated with the isocyanate group of TDI-forming urethane (ROGAU; Scheme 3), which formed ambient-cured coatings on CS panels.

Scheme 1 Synthesis of HERA.
Scheme 1

Synthesis of HERA.

Scheme 2 Synthesis of ROGA.
Scheme 2

Synthesis of ROGA.

Scheme 3 Synthesis of ROGAU.
Scheme 3

Synthesis of ROGAU.

3.1 Spectral analysis

The structures of HERA, ROGA, and ROGAU were confirmed by FTIR and NMR analyses.

3.1.1 FTIR (υ, cm−1)

FTIR spectrum of RO (Figure 1a) reveals the presence of characteristic absorption bands for –C═C–H str (3008.00 cm−1), –CH2– (assym), –CH3– (assym) (2923.25 cm−1), –CH2– (sym), –CH3– (sym) (2854.05 cm−1), –C═O (ester) (1747.39 cm−1), –C═C– (1654.39 cm−1), –C–C(═O)–O (1238.86 and 1163.49 cm−1), and –O–C–C– (1119.83 cm−1).

Figure 1 FTIR spectra of: (a) RO and HERA, (b) ROGA and ROGAU, and (c) Curing of ROGAU.
Figure 1

FTIR spectra of: (a) RO and HERA, (b) ROGA and ROGAU, and (c) Curing of ROGAU.

FTIR spectrum of HERA (Figure 1a) shows absorption bands as observed in RO at 3008.12 cm−1 (C═C), 2853.34 and 2923.73 cm−1 (–CH3, –CH2 stretching), 1614.99 cm−1 (>C═O amide), 1466.50–1366.08 cm−1 (–CH3, –CH2 bending), and 3391.33 cm−1 (–OH).

Here, the absorption band characteristic for the ester functional group as observed in RO at 1745 cm−1 is absent, while a new band is evident at 1614.99 cm−1 due to the amide functional group; this confirms the amidation reaction that consumes ester groups of RO-producing HERA.

FTIR spectrum of ROGA (Figure 1b) shows absorption bands at 3305.67 cm−1 (–OH, broad), 3,008.28 cm−1 (C═C), 2853.99 and 2925.08 cm−1 (–CH3, –CH2 stretching), 1737.16 cm−1 (>C═O ester), 1614.36 cm−1 (>C═O amide), 1467.29–1361.12 cm−1 (–CH3, –CH2 bending), 1361.12 cm−1 (phenolic –C–OH of GA), 1259.36–1,064.79 cm−1 (–(C═O)–O–C, –C–O–), 1556.86, 771.97, and 720.56 cm−1 (Ar–C═C–H; Ar = aromatic ring), as typical for the functional groups present in VO-based PEA. The hydroxyl band is broad owing to the plurality of hydrogen-bonded hydroxyl groups from HERA and GA.

FTIR spectrum of ROGAU (Figure 1b) also reveals the presence of some of the absorption bands as in ROGA, at 3287.37 cm−1 (–OH and –NHurethane), 3005.95 cm−1 (C═C), 2856.40 and 2926.17 cm−1 (–CH3, –CH2 stretching), 2272.79 cm−1 (–NCO), 1732.37 cm−1 (>C═O ester), 1610.86 cm−1 (>C═O amide), 1471.56–1365.25 cm−1 (–CH3, –CH2 bending), 1365.25 cm−1 (phenolic –C–OH of GA), 1226.88–1059.67 cm−1 (–(C═O)–O–C, –C–O–), and 1537.98 and 764.91 cm−1 (Ar–C═C–H). New bands are visible between 1,500 and 1,400 cm−1 due to amide of urethane.

3.1.2 1H NMR (CDCl3, δ, ppm)

RO: 5.26–5.29 ppm (–HC═HC–), 4.09–4.24 ppm (–CH 2–CH–glycerolic), 2.70–2.73 ppm (–CH 2 flanked by –CH═CH), 2.23–2.27 ppm (–CH 2 attached to >C═O ester), 1.21–1.98 ppm (–CH 2 chain), and 0.81–0.92 ppm (–CH 3) (Figure 2a).

Figure 2 1H NMR spectra of (a) RO (b) HERA, (c) ROGA and ROGAU.
Figure 2

1H NMR spectra of (a) RO (b) HERA, (c) ROGA and ROGAU.

HERA: 5.30–5.40 ppm (–CH═CH–), 4.34 ppm (–OH), 3.7 ppm (–CH 2–OH), 3.43–3.49 ppm (–CH 2–N–), 2.71–2.73 ppm (–CH═CH–CH 2–CH═CH–), 2.32–2.34 ppm (–CH 2–C(═O) –N–), 1.96–2.01 ppm (–CH–CH 2–CH═CH–), 1.15–1.56 ppm (–CH 2–), and 0.83 ppm (–CH 3) (Figure 2b).

ROGA: 6.89–6.33 ppm (Ar–H GA ), 6.18–6.17 ppm (Ar–OH GA ), 5.26–5.39 ppm (–CH═CH–), 4.03–4.17 ppm (–CH 2–O–C(═O)–), 3.52–3.62 ppm (–N–CH 2 –CH2 –O–C(═O)–), 3.40–3.46 ppm (–N–CH 2 –CH2 –OH), 3.256–3.306 ppm (–N–CH2 –CH 2 –OH), 2.50–2.72 ppm (–CH═CH–CH 2 –CH═CH–), 2.07–2.17 ppm (–CH 2 –C(═O)–N–), 1.08–1.92 ppm (–CH 2 –), and 0.87 ppm (–CH 3) (Figure 2c).

ROGAU: 8.24 ppm (–NH–), 7.07–7.20 ppm (Ar–H TDI), 6.36–6.93 ppm (Ar–H GA ), 6.22–6.23 ppm (Ar–OH GA ), 5.26 ppm (–CH═CH–), 4.15 ppm (–CH 2 –O–C(═O)–), 3.28–3.53 ppm (–N–CH 2 –CH 2 –O–C(═O)–), 2.68 ppm (–CH═CH–CH 2 –CH═CH–), 2.36–2.48 ppm (–CH 2 –C(═O)–N–), 1.17–1.77 ppm (CH 2 ), and 0.83 ppm (–CH 3 ) (Figure 2c).

3.1.3 13C NMR (CDCl3, δ, ppm)

RO: 172.68–173.08 ppm (>C═O), 129.67–130.11 ppm (–CH═CH–), 62.08 and 68.92 ppm (–CH2 –O–, –CH–O– glycerolic), 34.0–22.74 ppm (–CH2chain), and 14.11–14.15 ppm (–CH3) (Figure 3a).

Figure 3 13C NMR spectra of (a) RO, (b) HERA, (c) ROGA and ROGAU.
Figure 3

13C NMR spectra of (a) RO, (b) HERA, (c) ROGA and ROGAU.

HERA: 175.70 ppm (>N–C═O), 129.78–130.03 ppm (–CH═CH–), 60.39–61.19 ppm (>N–CH2 CH2 –OH), 52.26–50.53 ppm (>N–CH2CH2 –OH), 34.0–22.0 ppm (CH2chain), and 15.28–14.12–14.16 ppm (–CH3) (Figure 3b).

ROGA: 175.75 ppm (>N–C═O), 172.35 ppm (>C═Oester), 145.23–146.42 ppm (Ar GA, (m)–C–OH), 133.21 ppm (Ar GA, (p)–C–OH), 129.62–126.97 ppm (–CH═CH–), 118.34 ppm (Ar GA > C–C═O), 107.06–108.72 ppm (Ar GA, (HO)–C–C–C–(C═O)–), 58.89–59.37 ppm (>N–CH2 CH2 –OH), 51.01–48.32 ppm (>N–CH2CH2 –OH), 34.87–20 ppm (CH2chain), and 13.94 ppm (–CH3) (Figure 3c).

ROGAU: 175–173.05 ppm (>C═Oester,amide), 154–158 ppm (>C═Ourethane), 147.11–146.79 ppm (Ar GA,(m)–C–OH), 133.64 ppm (Ar GA,(p)–C–OH), 128–124.74  ppm (–CH═CH–), 118.91 ppm (Ar GA, >C–C═O), 107.59 ppm (Ar GA, (HO)–C–C–C–(C═O)–), 60.72–59.45 ppm (>N–CH2 CH2 –OH), 51.08–48.87 ppm (>N–CH2CH2 –OH), 34.46–20.56 ppm (CH2,chain), 17.30–17.58 ppm (–CH3,TDI), and 14.40 ppm (–CH3) (Figure 3c). The additional peaks appear between 137 and 124 ppm due to aromatic carbons of TDI (26).

On closer observation, it is distinct that the peak due to carbon attached to the –OH group (>N–CH2 CH2 –OH between 58 and 60 ppm) in HERA is also dominant in ROGA, while the same peak appears very much depressed in ROGAU, thus confirming the consumption of OH groups of ROGA during urethanation reaction with isocyanate; peaks of carbon attached to hydroxyl of GA appear unchanged during urethanation. Spectral analyses show that GA has been incorporated in ROGA through esterification reaction between hydroxyl of HERA and carboxylic hydroxyl of GA, and subsequently in ROGAU too, as confirmed by the presence of additional absorption bands and peaks of GA in ROGA and ROGAU, thus confirming the development of RO gallate amide and gallate amide urethane (10,11,27,28,29,30,31).

3.2 Coating properties

3.2.1 Curing/drying of coatings

Curing/drying of VO-based PU coating occurs by the reaction of free-NCO groups of polymer chains with atmospheric moisture, followed by auto-oxidation at double bonds (30). ROGAU was applied on CS panels and FTIR (Figure 1c) spectra were recorded at the intervals of 5 min, 2 h, and 1 day to study the curing/drying reaction of the coating material. Curing of ROGAU was closely monitored by the change in the absorption band intensity of –NCO of ROGAU in FTIR, after application over CS panel for drying/curing. In freshly prepared ROGAU, –NCO band appeared as an intense band at 2270.60 cm−1, along with the other bands at 3287.37 cm−1 (–OH), 3005.95 cm−1 (H–C═C–), 1732.37 cm−1 (>C═O ester), and 1620.16 cm−1 (>C═O amide). In ROGAU (2 h), –NCO appeared as a suppressed band showing much diminished –NCO band compared to ROGAU (5 min), and finally in ROGAU (1 day), –NCO band appears as a suppressed hump. These results clearly confirm the participation of –NCO in drying/curing reaction.

The free-NCO groups react with atmospheric moisture forming (unstable) carbamic acid that dissociates into an amine-terminated backbone, liberating carbon dioxide (Scheme 4). The amine-terminated prepolymer reacts with either free-NCO of TDI or the free-NCO moiety of another ROGAU chain producing urea linkages, and thus, the curing reactions occur at room temperature facilitated by atmospheric moisture (32). Further curing proceeds by crosslinking due to double bonds (auto-oxidation).

Scheme 4 Curing mechanism.
Scheme 4

Curing mechanism.

3.2.2 Physico-mechanical analysis

Coatings of ROGAU-30, ROGAU-35, and ROGAU-40, with thickness of 130 µm and gloss 60°, were prepared on CS panels at ambient temperature and were then subjected to morphology analysis and performance evaluation tests.

All coatings passed impact resistance (26.786 kg·cm−1), bending test (0.317 cm conical mandrel bend test), and cross-hatch (95%) adhesion test, which showed that coatings are well adhered to CS panels. This is because of the presence of polar hydroxyl, amide, and urethane functional groups in ROGAU backbone conferred by GA and TDI that introduce amide, three (additional) hydroxyl groups, and urethane groups, respectively. Scratch hardness and pencil hardness of coatings varied from 1.8 kg, 1H (ROGAU-30), 2.0 kg, 3H (ROGAU-35), and 1.5 kg, 2H (ROGAU-40) with the increased content of urethane by increasing the inclusion of TDI from 30, 35, to 40 wt% due to increased crosslinking within the polymeric chains. At ROGAU-40, with higher TDI content, i.e., 40 wt%, the physico-mechanical properties of coatings deteriorated due to stiffness caused by higher aromatic and urethane content. Thus, ROGAU-35, with 35 wt% TDI, which is considered as the optimum loading of TDI, showed the best physico-mechanical performance, and hence, ROGAU-35 was subjected to morphology, hydrophobicity, and corrosion resistance tests as discussed in proceeding sections.

Morphology of ROGAU studied by SEM (Figure 4a) reveals homogeneity and intactness of ROGAU matrix, without any cracks, pinholes, or bubbles. SEM (Figure 4b) after immersion in 3.5% NaCl solution (w/w) for 9 days shows that the coating is well adhered to the substrate, without any loss in integrity or texture but with few crystals of NaCl salt deposited on the surface.

Figure 4 SEM image of (a) ROGAU-coated and (b) ROGAU-coated CS after immersion.
Figure 4

SEM image of (a) ROGAU-coated and (b) ROGAU-coated CS after immersion.

The water contact angle of ROGAU coating (Figure 5) was found to be 80°, which is indicative of the wetting nature of ROGAU coating surface. Hydrophobicity is an important aspect of coatings as the hydrophobic nature of coatings facilitates their corrosion resistance performance in corrosive media such as water, acid, alkali, and salt solutions. The ROGAU contact angle less than 90° suggests that this coating material holds immense scope for further modification with a view to improve the hydrophobicity characteristic of coating.

Figure 5 Contact angle of ROGU-coated CS.
Figure 5

Contact angle of ROGU-coated CS.

3.3 Corrosion resistance

3.3.1 EIS study

Nyquist plots of ROGAU were obtained at various times (1, 3, 5, 7, and 9 days) of immersion in a solution of 3.5 wt% NaCl as displayed in Figure 6a. Only one type of equivalent circuit model fitted in the impedance spectra, (which have commonly been proposed for coating systems), were employed to interpret impedance response. The equivalent circuit values displayed Rs electrolyte resistance, Cc coating capacitance, and R ct charge transfer resistance in Table 1. The values of EIS parameters and the size of the capacitive loop behavior of coatings showed that as the immersion time increases, the size of the capacitive loop decreases. The variation of the values of Cc and R ct is extracted from the impedance diagram with immersion time. Cc decreases with the immersion time up to 7 days and then it slightly increases in the presence of chloride ions on coated panel, whereas R ct decreases with time; after 9 days of immersion, no sign of substrate corrosion was observed. The values of ROGAU showed higher impedance at the lowest frequency region, which is the characteristic for the shielding ability of coating, and the resistance to corrosive ions seems to decrease with the increase in corrosive ion exposure time due to possible permeation of ions to the coating surface. Figure 6b, bode plot of ROGAU, also shows a high-frequency region with a high-phase angle initially, whereas the time of exposure increases, which can be attributed only to the intact and well-adhered coating surface. The low-phase angle value at low frequency indicates diffusion of corrosive ions toward ROGAU coating with metal interface possibly through inherent micro-porosity of the ROGAU coating surface, while the higher phase angle value and high-frequency range are indicative of the intactness of ROGAU coating (33). After 11 days of exposure in the corrosive medium, the phase angle value remained between 80 and 90, and it supported the negligible value of delamination of ROGAU coating due to its cross-linked structure, which acts as a barrier on MS surface coating (34,35).

Figure 6 (a) EIS spectra of ROGAU-coated CS and (b) Bodetheta plot of ROGAU-coated CS.
Figure 6

(a) EIS spectra of ROGAU-coated CS and (b) Bodetheta plot of ROGAU-coated CS.

Table 1

Presents the electrochemical impedance (EIS) parameter for ROGAU coating under 3.5 wt% NaCl solution at room temperature

Immersion time (days) R s (Ω) R ct (kΩ) Coating capacitance (pF) χ 2
1 180 109 563 1.41
3 133 136 556 1.40
5 121 184 527 1.30
7 129 131 518 1.11
9 135 61.5 568 1.21

3.3.2 Polarization study

Corrosion resistance performance of ROGAU-coated panels was examined electrochemically using potentiodynamic polarization (PDP) for a period of 9 days in 3.5 wt% NaCl solution at room temperature (Figure 7). Corrosion parameters such as corrosion potential (E corr), corrosion current (I corr), corrosion rate (CR), and linear polarization resistance (LPR) were derived from Tafel plots as presented in Table 2. The measured value of corrosion current (I corr) of ROGAU after 9 days immersion is 3.007 × 10−7. CR increases and LPR of the coated panel decreases during immersion periods. On comparing the value of Icorr of ROGAU-coated panels with immersion periods, it is clearly observed that the corrosion current of ROGAU-coated specimens is almost two to three orders of magnitude less than the bare MS (36). The occurrence of significantly low Icorr for ROGAU-coated specimen indicates the existence of protective barrier film that prevents the entrance of electrolyte into ROGAU coating and MS boundary. Accordingly, the CR values are also decreased with immersion time in the presence of chloride ions. The application of ROGAU coating offers effective corrosion protection to the MS substrate by developing a good protective layer that separates the metal surface from corrosive environments and renders efficient barrier property to the coating surface to hamper the diffusion of corrosive electrolytes (37).

Figure 7 Tafel plot of ROGAU-coated CS.
Figure 7

Tafel plot of ROGAU-coated CS.

Table 2

The Tafel parameters for ROGAU coating under 3.5 wt% NaCl solution at room temperature

Immersion time (days) E corr (V) I corr (A·cm−2) CR (mm·year−1) LPR (Ω)
1 −0.011 9.383 × 10−8 1.094 × 10−3 3.350 × 105
3 −0.018 1.085 × 10−7 1.260 × 10−3 3.309 × 105
5 −0.032 5.423 × 10−7 1.095 × 10−3 3.647 × 105
7 −0.046 1.379 × 10−7 1.602 × 10−3 2.582 × 105
9 −0.103 3.007 × 10−7 3.494 × 10−3 1.314 × 105

3.3.3 Thermogravimetric analysis and differential scanning calorimetry

TGA thermograms of ROGA and ROGAU (Figure 8) showed first 10 wt% degradation around 200°C, followed by 50 wt% loss from 350°C to 375°C. In DSC thermograms of ROGA and ROGAU (Figure 9), first endotherm appeared between 100°C and 125°C in ROGA and ROGAU due to evaporation of the trapped solvent. The second broad endothermic event was observed in both ROGA and ROGAU from 150°C to 300°C. Similar decomposition events were also observed in DTG thermogram (Figure 8). Slight variation in thermal stability of ROGA and ROGAU is observed from 200°C to 325°C; ROGA showed higher thermal stability relative to ROGAU, while ROGAU exhibited higher percent weight loss (based on percent weight loss vs temperature); therefore there is a scope for further improvement in thermal stability of ROGAU. Generally, urethane bonds degrade at temperatures above 200°C by three decomposition pathways, first generating isocyanate and alcohol moieties, second yielding olefins and primary amines, and third resulting in secondary amine and carbon dioxide. The slightly low thermal stability of ROGAU compared to ROGA was due to the presence of urethane bonds in the former; therefore, there is a scope for further improvement in the thermal stability of ROGAU (38). Thermal stability in ROGA is conferred by amide, ether groups, and alkyl chains of HERA (39). 75 wt% degradation occurred in both ROGA and ROGAU around 425°C. TGA thermograms revealed that ROGA and ROGAU showed comparable thermal stability. Both ROGA and ROGAU may be safely used up to 200°C.

Figure 8 TGA/DTG thermogram of ROGA and ROGAU.
Figure 8

TGA/DTG thermogram of ROGA and ROGAU.

Figure 9 DSC thermogram of ROGA and ROGAU.
Figure 9

DSC thermogram of ROGA and ROGAU.

4 Conclusion

The substitution of sustainable resource-based polymers in place of petro-based chemicals has attracted attention due to health and environmental hazards posed by the latter. This article reports the synthesis of RO gallate amide-based polyurethane for the first time. Coatings showed good physico-mechanical and corrosion resistance performance. However, the hydrophobicity (contact angle less than 90°) and thermal stability (by TGA) results indicate that the coating material holds immense scope for further modification to improve hydrophobicity and thermal stability of coatings to be employed as high-performance coatings, which can be accomplished in our future research work. The coatings can be safely employed up to 200°C. The approach describes a new pathway to utilize vegetable oils by gallation and subsequent urethanation reaction and can be applied on nonedible, nonmedicinal, and abundantly available seed oils as a small step toward sustainable development.

Acknowledgements

The authors are grateful to the Researchers Supporting Project no. RSP-2021/113, King Saud University, Riyadh, Saudi Arabia, for the support.

  1. Funding information: Researchers Supporting Project no. RSP-2021/113, King Saud University, Riyadh, Saudi Arabia.

  2. Author contributions: Manawwer Alam: writing – original draft, methodology, formal analysis; Mohammad Altaf: formal analysis, visualization; Naushad Ahmad: formal analysis resources; writing – review and editing.

  3. Conflict of interest: The authors state no conflict of interest.

References

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Received: 2021-08-19
Revised: 2021-12-15
Accepted: 2021-12-15
Published Online: 2022-02-15

© 2022 Manawwer Alam et al., published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

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  3. The effect of different structural designs on impact resistance to carbon fiber foam sandwich structures
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  7. Fabrication of flexible conductive silk fibroin/polythiophene membrane and its properties
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  14. Preparation and electroactuation of water-based polyurethane-based polyaniline conductive composites
  15. Rapeseed oil gallate-amide-urethane coating material: Synthesis and evaluation of coating properties
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https://doi.org/10.1515/epoly-2022-0021
Keywords for this article
rapeseed oil; gallic acid; polyurethane; coatings
Creative Commons
BY 4.0

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  3. The effect of different structural designs on impact resistance to carbon fiber foam sandwich structures
  4. Hyper-crosslinked polymers with controlled multiscale porosity for effective removal of benzene from cigarette smoke
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