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Industrial Crops and Products 57 (2014) 1728
Contents lists available at ScienceDirect
Industrial Crops and Products
jo ur nal home p age: www.elsev ier .com/ locate / indcrop
orn oil based poly(ether amide urethane)
coatingaterialSynthesis, characterization and coating
properties
anawwer Alama,, Naser M. Alandisb
Research Center-College of Science, King Saud University, P.O.
Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry,
College of Science, King Saud University, P.O. Box 2455, Riyadh
11451, Saudi Arabia
r t i c l e i n f o
rticle history:eceived 23 November 2013eceived in revised form 9
March 2014ccepted 19 March 2014vailable online 7 April 2014
eywords:orn oil
a b s t r a c t
Polyetheramide (CPETA) resin was synthesized from N,N-bis
(2-hydroxy ethyl) corn oil fatty amide(HECFA) and catechol through
condensation polymerization. CPETA was further cured with
isophoronediisocyanate (IPDI) in different weight percentage (20,
25, 30, 35, 40 wt.%) to obtain poly(ether amideurethane) (CPETAU).
The structural elucidation of HECFA, CPETA and CPETAU was carried
out by FT-IR,1H NMR and 13C NMR spectroscopic techniques.
Physico-chemical and physico-mechanical propertiesof these resins
were investigated by standard methods. Thermal behavior was
assessed by thermogravi-metric analysis (TGA) and differential
scanning calorimetry (DSC). The corrosion resistance
performanceolyetheramiderethaneatechol
of CPETAU coatings on mild steel strips was investigated by
potentiodynamic polarization studies indifferent corrosive media
(3.5 wt.% HCl, 5.0 wt.% NaCl, tap water) at room temperature.
Amongst all thecompositions, CPETAU coatings showed good scratch
hardness (2.20 kg), impact resistance (150 lb/inch),gloss with
corrosion rate obtained as 1.377 102 (mm/year) and 2.359 103
(mm/year) in 3.5 wt.% HCland 5.0 wt.% NaCl solution, respectively.
CPETAU coatings can be safely used up to 250 C.
2014 Elsevier B.V. All rights reserved.. Introduction
Vegetable oils (VO) are one of the most important raw mate-ials
for chemical industry. VO can be transformed into variousroducts
used in different applications such as biodiesel, soaps,osmetics,
adhesives, inks, paints and coatings industries (Barnwalnd Sharma,
2005; Maisonneuve et al., 2013; Sharma and Kundu,006, 2008; Galia
et al., 2009). VO such as linseed, castor, soy-ean, argemone,
Pongamia glabra, Jatropha curcas, rubber seed,nnona squamosa,
sunflower and olive are used in the synthesisf different polymers
like alkyds, polyesteramides, polyurethanes,olyetheramides,
polyepoxies, and poly(amine-amides) (Alamt al., 2009a; Can et al.,
2006; Chen et al., 2011; Kumar et al.,010; Alam and Alandis, 2012a;
Alam et al., 2004, 2010; Alam andlandis, 2012b; Alam et al., 2008,
2009b). VOs are good chemicaleedstocks due to many advantages such
as presence of functionalroups for chemical transformations,
physical, chemical stability,educed toxicity, eco-friendliness,
biodegradability, and flexibil-
ty (Guner et al., 2006; Hojabri et al., 2009; Sharmin et al.,
2007;haudhari et al., 2013; Kumar et al., 2008). VOs are mainly
con-tituted by triglycerides, which are the products of
esterification
Corresponding author. Tel.: +966 554738803.E-mail address:
[email protected] (M. Alam).
ttp://dx.doi.org/10.1016/j.indcrop.2014.03.023926-6690/ 2014
Elsevier B.V. All rights reserved.reaction between a molecule of
glycerol and three molecules offatty acids. The properties and
reactivity of triglycerides stronglydepend on their composition
(Petrovic, 2008; Scala and Wool,2005).
Corn oil is extracted from the germ of corn (maize) and usedin
the field of biodiesel, soaps, paints and coatings
industries(Kadioglu et al., 2011; Perkin et al., 2005). Major
productionof corn oil occurs in USA, China, Brazil, Mexico,
Indonesia,India, France, Argentina, South Africa, and Ukrane (Saso
et al.,2013; Lu and Larock, 2006). Catechol (benzene-1,2 diol) isa
natural compound that was discovered by destructive dis-tillation
of the plant extract of Catechin. Catechol is widelyused in
coordination chemistry as chelating agent and pro-duction of
pesticides, fine chemicals, and others (Sedo et al.,2013; Hong et
al., 2013).
Polyurethanes are synthesized by the reaction of polyols
andisocyanates. Different isocyanates like
toluylene-2,4-diisocyanate(TDI), hexamethylene diisocyanate (HMDI),
isophorone diiscyanate(IPDI), and others are used for the synthesis
of polyurethane for dif-ferent applications (Petrovic, 2008;
Lligadas et al., 2010; Ducruetet al., 2013). PU finds versatility
application in the synthesis of dif-
ferent materials such as foams, coatings, adhesives, sealants
andelastomers.
In this research work we have developed polyetheramide
resin(CPETA) using N,N bis 2-hydroxyethyl corn oil fattyamide
(HECFA)
dx.doi.org/10.1016/j.indcrop.2014.03.023http://www.sciencedirect.com/science/journal/09266690http://www.elsevier.com/locate/indcrophttp://crossmark.crossref.org/dialog/?doi=10.1016/j.indcrop.2014.03.023&domain=pdfmailto:[email protected]/10.1016/j.indcrop.2014.03.023
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18 M. Alam, N.M. Alandis / Industrial Crops and Products 57
(2014) 1728
Scheme 1. Synthesis of HECFA.
Scheme 2. Synthesis of CPETA.
nthes
aftIrt
Scheme 3. Sy
nd catechol through condensation polymerization. CPETA wasurther
converted into polyurethane (CPETAU) by chemical reac-
ion between free hydroxyl groups of CPETA and NCO group ofPDI in
different percentages (25, 30, 35, 40 wt.%). The preparedesins were
characterized by FT-IR, 1H NMR and 13C NMR spec-roscopic
techniques. The physico-chemical characterizations ofis of
CPETAU.
these resins were performed by standard laboratory methods.The
thermal stability and curing behavior of these resins were
investigated by thermogravimetric analysis (TGA) and
differentialscanning calorimetry (DSC). The coatings of CPETAU were
preparedon mild steel strips of standard sizes to evaluate their
physico-mechanical behavior. The corrosion resistance performance
was
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M. Alam, N.M. Alandis / Industria
tudied by potentiodynamic polarization measurements at
roomemperature. The knowledge added in the above area would
beioneering and lead to great reliability of these materials for
tech-ological exploitation.
. Materials and methods
Corn oil (Afia International Company, Jeddah) was procuredrom
local market. The fatty acid composition of corn oil wasetermined
using methyl esters on Hewlett-Packard 5890 SeriesI gas
chromatography with FID detector. The fatty acid com-osition of
Corn oil was obtained as: linoleic acid 58.3%, oleiccid 26.1%,
palmitic acid 10.5%, linolenic 1.1%, stearic acid
2.1%.iethanolamine (Riedel-deHaen, Germany), Methanol, CatecholBDH
Chemicals, Ltd. Poole, England), Isophorone
diisocynate3-isocyanatomethyl-3,5,5-trimethylcyclohexylisocyanate)
(Acrosrganics, USA) were used as received.FT-IR spectra were taken
on FT-IR spectrophotometer (Prestige-
1, FT-IR-8400S, Shimadzu Corporation, Kyoto Japan) using
NaClell. 1H NMR and 13C NMR spectra were recorded on a JeolPX400
MHz using deuterated chloroform (CDCl3), deuteratedimethyl
sulphoxide(DMSO) as solvent and tetramethylsilaneTMS) as an
internal standard. Thermal analysis was carried outy TGA/DSC1
(Mettler Toledo AG, Analytical CH-8603, Schwerzen-ach,
Switzerland), in nitrogen atmosphere at heating rate of
0 C/min. The physico-chemical characteristics such as iodinealue
(ASTM D1959-97), hydroxyl value (ASTM D1957-86) andefractive index
were observed by standard methods. Scratch hard-ess (BS 3900),
impact test (IS:101 part 5 s1, 3,1988) and bend test
Fig. 1. 1H NMR specs and Products 57 (2014) 1728 19
values(1/8 inch conical mandrel, ASTM D3281-84), Pencil
hardness(Wolff-wilborn tester, sheen instruments, England) and
speculargloss of the coating was found 130 5 m measured at 45 by
Glossmeter (Model RSPT 20; digital instruments, Santa Barba, CA,
USA),Elcometer (Model 345; Elcometer instruments, Manchester,
UK).
The corrosion resistance behavior of the CPETAU coated
mildsteel(MS) substrate by potentiodynamic polarization
measurementstudies using potentiostat analyzer of Gill AC (ACM
Instruments,UK) in different aggressive media: 3.5 wt.%HCl, 5.0
wt.% NaCl, andtap water (Cl ion 163.303 ppm) for evaluation of
their corro-sion resistance behavior. The corrosion inhibition
efficiency ofcoatings was assessed relative to bare mild steel
panels (Fe = 99.51%,Mn = 0.34%, C = 0.10%, P = 0.05%). The
potentiondynamic polariza-tion curves were prepared by polarizing
the working electrode at250 mV in relation to the free corrosion
potential at a scanningrate of 1 mV/s (exposed surface area 1 cm2).
The electrochemicalsystem was completed with a platinum counter
electrode, calomelas reference and coated mild steel as working
electrode. The mea-surements were performed in triplicate. The
inhibition efficiencyof the coating was determined using corrosion
current of bare mildsteel and coated mild steel (Alam and Alandis,
2012b).
IE(%) = I0corr Icorr
I0corr 100I0corr and Icorr are the corrosion current density of
bare mild steeland coated mild steel.
The average molecular weight (Mw and Mn) and polydis-persity
index (PDI; Mw/Mn) were measured by gel permeation
tra of corn oil.
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0 M. Alam, N.M. Alandis / Industria
hromatography (GPC) with HT-GPC Module 350A,Viscotek Hous-an,
TX, USA. Tetrahydrofuran (THF) was used as an eluent at a flowate
1.0 mL/min. Molecular weight calibration was performed
witholystyrene standard. The molecular weight observed of CUPETA5
is 8356 (Mw), 4645(Mn), and PDI, 1.79.
.1. Synthesis of N,N-bis(2-hydroxy ethyl) corn oil fatty
amideHECFA)
Diethanolamine (0.32 mol) and sodium methoxide (0.007 mol)ere
mixed in a round bottom flask fitted with a magnetic stir-er,
thermometer and dropping funnel. The contents were heatedt 120 C.
Corn oil (0.1 mol) was added drop wise into the reac-ion mixture
over a period of 1 hour. The progress of reaction wasonitored by
thin layer chromatography (TLC) at regular intervalsf time. After
completion of reaction, the product was dissolvedn diethyl ether,
and washed with 15% aqueous NaCl solutionnd dried over anhydrous
sodium sulfate. The ethereal solution ofECFA was filtered and
solvent was evaporated in rotary vacuumvaporator to obtain HECFA
(Alam and Alandis, 2012b).
.2. Synthesis of polyetheramide (CPETA)
HECFA (0.02 mol) and catechol (0.02 mol) were dissolved in
mix-
ure of xylene (50 mL) and ethyl methyl ketone (25 mL), and 1
mLilute sulfuric acid as a catalyst in four necked round bottom
flaskquipped with Dean Stark trap, nitrogen inlet tube,
thermometer,nd magnetic stirrer. The reaction mixture was heated at
105 C
Fig. 2. 13C NMR specs and Products 57 (2014) 1728
and refluxed until the theoretical amount of water was collected
inDean stark trap. The reaction was monitored by TLC and
hydroxylvalue determination at regular intervals of time. After
completion ofreaction, the solvent was evaporated in rotary vacuum
evaporatorunder reduced pressure to obtain CPETA.
2.3. Synthesis of poly(ether amide urethane) (CPETAU)
CPETA and IPDI (20, 25, 30, 35, 40 wt.%) in xylene and
ethylmethyl ketone (1:1) were placed in four neck round bottom
flaskfitted with cold water condenser, thermometer, nitrogen inlet
tubeand magnetic stirrer. The reaction was carried out under
stirringat 120 C. The reaction was monitored by TLC and hydroxyl
valuedetermination at regular intervals of time. The solvent was
evapo-rated in a rotary vacuum evaporator at reduced pressure to
obtainCPETAU.
3. Results and discussion
Schemes 13 illustrate the synthesis of HECFA by the
aminolysisreaction of corn oil and diethanolamine, CPETA synthesis
by con-densation polymerization reaction of HECFA and Catechol and
theformation of CPETAU by addition polymerization reaction
between
CPETA and IPDI, respectively. The proposed reaction schemes
andthe structures of the final product were confirmed by the
presenceof characteristics bands and peaks in FT-IR, 1H NMR and 13C
NMRspectra.
tra of corn oil.
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M. Alam, N.M. Alandis / Industria
.1. Spectral analysis
.1.1. Corn oilFT-IR (cm1): 3474; 3008( CCH
H C); 2926(CH2, asymmetrical); 2854(CH2, symmetrical);746(C O,
ester); 1654( CCH CH C ); 1238, 1163( CCOO C);100( CO CC CC).
1H NMR, CDCl3, , ppm: 5.265.27( CCH CH C);.23(>CHOCO CH2 C);
4.074.08(CCH2 COCO CH2 C);.70( CH CCH2 CCH ); 2.23( OCO CH2 );
1.941.98( CH2H CH ); 1.54( O CO CH2 CH2 CH2); 1.191.23( CH2
);.800.81(CH3) (Fig. 1).
13C NMR CDCl3, ppm: 172.56172.95(C O); 127.8930.04( CH CH );
68.92( OCH2 CHCHOCO CH2);1.55( CH2 CH2 CH2 CH CH 29.1229.38( CH2 );
27.197.21( CH2 CH3) 14.07( CH3) (Fig. 2).
.1.2. HECFAFT-IR (cm1): 3425(OH); 1623(C O, amide); 1464(C
N,
mide); 2926(CH2, asymmetrical); 2850; (CH2, sym-etrical); 3005(
CH CH ), 1H NMR, CDCl3, ppm:.80(CH3); 1.1461.251( CH2 ); 3.413.46(
CH2OH);
.2775.310( CH CH ); 4.80 ( CH2OH) (Fig. 3).
13C NMR, CDCl3, ppm: 14.0914.14(CH3); 22.302.10( CH2 );
60.3960.93( CH2OH); 127.92130.22( CHH ); 175.57(C O, amide) (Fig.
4).
Fig. 3. 1H NMR specs and Products 57 (2014) 1728 21
3.1.3. CPETAFT-IR (cm1): 3387(OH); 1275, 1097 ( C O C ,
ether);
1619(C O, amide); 1464(C N, amide); 2926(CH2,
asymmetrical);2855; (CH2, symmetrical); 3008( CH CH ); 3087, 1513,
1432,770, 745(aromatic ring).
1H NMR CDCl3, ppm: 0.850.89( CH3); 1.251.27( CH2 );2.012.04( CH2
, attached double bond) 3.763.82( CH2 ,attached amide nitrogen);
4.25( CH2 attached O)5.325.34( CH CH ); 6.836.84(aromatic ring)
(Fig. 5).
13C NMR, CDCl3 ppm: 14.21( CH3); 2229( CH2 ); 31( CH2attached to
amide carbonyl); 52( CH2 attached to amidenitrogen);
115,120,158(aromatic ring); 176.35(C O, amide)(Fig. 6).
3.1.4. CPETAUFT-IR (cm1): 3315(OH); 1241, 1094( C O C ,
ether);
1619(C O, amide); 1464(C N, amide); 2926(CH2,
asymmetrical);2855; (CH2, symmetrical); 3007( CH CH ),
1725(urethane NH);3007,1542,748( CH CH , aromatic ring).
1H NMR, DMSO-d6, ppm: 0.850.87(CH3); 2.002.02( CH2 ,
attached double bond) 3.763.82( CH2 , attached amidenitrogen);
4.30( CH2 attached O) 5.315.33( CH CH );6.606.73(aromatic ring),
1.46(CH2, cyclic); 7.90( NH, urethane)(Fig. 7).
tra of HECFA.
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22 M. Alam, N.M. Alandis / Industrial Crops and Products 57
(2014) 1728
R spe
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Fig. 4. 13C NM
13C NMR, DMSO-d6, ppm: 14.49( CH3); 2229( CH2 );1( CH2 attached
to amide carbonyl); 52( CH2 attached to amideitrogen);
116,119,145(aromatic ring); 176.35(C O, amide); 153free NCO);
162(CO, urethane) (Fig. 8).
.2. Physico-chemical analysis
Table 1 indicates that hydroxyl and iodine values decreaserom
HECFA, CPETA and subsequently to CPETAU25, CPETAU30,PETAU35, and
CPETAU40. The following trend is correlated to
he reaction of HECFA with Catechol to form PETA resulting in
anncrease in molecular weight; the molecular weight of CPETAU
fur-her increases with increase in the amount of IPDI. The
hydroxylalues decrease because of the consumption in hydroxyl
groups of
able 1hysico-chemical characterization of resins.
Resin code* R. Index I. Viscosity
Corn Oil 1.4701 HECFA 1.4891 0.6581 CPETA 1.5050 0.6989 CPETAU25
1.512 0 0.7042 CPETAU 30 1.5196 0.7058 CPETAU 35 1.5230 0.7166
CPETAU40 1.5237 0.7195
Last numeral digit indicate the loading of IPDI.cid value of
corn oil: 5.91, Saponification value: 189, R. index Refractive
index, I. visalue.ctra of HECFA.
the resins by chemical reaction with free -NCO groups of IPDI
form-ing urethane linkages. As a result hydroxyl values decrease
and alsodecrease in iodine values is observed.
3.3. Physico-mechanical properties of coating
The coatings were cured at room temperature. The drying timesof
these coatings were found as 30 minutes. According to the
resultsfrom Table 2, it can be seen that scratch hardness values
werefound to increase up to CPETAU35 after that decrease in
scratch
hardness were observed it is likely that the additional NCO
group isliable to give too much cross linking. The optimum required
limit,as result film showed brittleness because besides urethane
forma-tion, there are other secondary reactions which predominate
such
S. Gravity H. Value I. Value
0.918 1270.938 6.87 720.944 4.56 380.950 3.63 320.956 3.25
300.961 2.93 290.963 2.57 25
cosity Inherent viscosity, S. gravity Specific gravity at 25 C,
I. value Iodine
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M. Alam, N.M. Alandis / Industrial Crops and Products 57 (2014)
1728 23
1 R spec
atchtopb
3
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Fig. 5. H NM
s allophanate formation. All the coatings passed 250 lb/in.
impactest, which showed good interaction between metal and
polymeroating due to the presence of polar groups such as carbonyl,
uret-ane group present in the polymeric chain. The coatings pass
bendest 1/8 in. on conical mandrel due to the presence of alkyl
chain ofil. The coatings showed gloss values between 66 and 75 at
45 andencil hardness test maximum 8H passed, showing good
bindingetween substrate and polymer coating.
.4. Corrosion tests
The potentiodynamic polarization studies of CPETAU coated MS
nd bare MS(blank) panels were carried out at room temperaturen
various corrosive media such as 5wt.%NaCl solution,
3.5wt.%HClolution and tap water for 380 h, 425 h and 144 h
immersionime, respectively. Fig. 9 shows the Tafel plots of bare
mild steel,
able 2hysico-mechanical characterization of coatings.
Resin code* S. Hardness (kg) I. Resistance (lb/inch)
CPETAU25 1.40 150 CPETAU30 1.80 150 CPETAU35 2.20 150 CPETAU40
2.00 150
Last numeral digit indicate the loading of IPDI in
percentage.oating thickness 80125 m.tra of CPETA.
CPETAU25, CPETAU30, CPETAU35, and CUPETAU40 coated MS in5 wt.%
NaCl solution after 380 h immersion. Table 3 illustrates
thecorrosion parameters for bare MS and coated MS with
CPETAUcoatings in 5 wt.% NaCl solution. It is mentioned that the
val-ues increased noticeably from CPETAU25, CPETAU30, CPETAU35,and
CPETAU40 coated MS. These results indicate that CPETAUcoatings can
act as protective layer on mild steel and improvethe overall
corrosion performance. The corrosion current valueswere found to
decrease with increase the amount of IPDI in CPETAresins likely
CPETAU25, CPETAU30, CPETAU35, and CPETAU40.The corrosion rate for
bare steel was found to be 2.676 mm/yearand it is minimized by
polymeric coating of CPETAU25,
CPETAU30, CPETAU35, and CPETAU40 to lower value 2.359 103
mm/year.
Fig. 10 shows the polarization curves of CPETAU coatedMS in
3.5wt.% HCl solution. For example (Table 3) the
Bend test (1/8 inch) Gloss (45) P. Hardness (pass)
Passes 66 2HPasses 70 3HPasses 73 8HPasses 75 6H
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24 M. Alam, N.M. Alandis / Industrial Crops and Products 57
(2014) 1728
Fig. 6. 13C NMR spectra of CPETA.
or7tC
TC
pen circuit potential, the corrosion potential, corrosion
cur-
ent density and corrosion rate changed from 485.08 mV,.580 101
mA/cm2 and 8.7862 mm/year for bare MS substrateo 82.748 mV, 1.182
103 mA/cm2, 1.377 102 mm/year forPETAU40, respectively. These
coatings confer barrier properties
able 3orrosion parameters for coated and bare mild steel strips
in different corrosive environm
Sample code Medium ECorr (mV) i Corr (mA/
Mild Steel 3.5 wt.% HCl 485.08 7.580 10CPETAU25 3.5 wt.% HCl
480.95 5.876 10CPEATU30 3.5 wt.% HCl 452.78 4.448 10CPEATU35 3.5
wt.% HCl 447.49 2.939 10CPEATU40 3.5 wt.% HCl 82.748 1.182 10Mild
Steel 5.0 wt.% NaCl 757.08 2.309 10CPTEAU25 5.0 wt.% NaCl 501.27
7.773 10CPETAU30 5.0 wt.% NaCl 446.65 2.967 10CPETAU35 5.0 wt.%
NaCl 357.45 3.351 10CPETAU40 5.0 wt.% NaCl 304.65 2.036 10Mild
Steel Tap water 638.42 2.217 10CPETAU25 Tap water 362.33 3.983
10CPETAU30 Tap water 333.46 7.917 10CPETAU35 Tap water 266.89 2.327
10CPEATU40 Tap water 227.00 5.955 10to MS panel. The intact organic
groups dispersed throughout the
coatings apparently serve to increase the hydrophobicity of
thecoatings, repelling water and corrosion ions and enhancing
cor-rosion protection properties, arising due to crosslinked
networkstructure of CPETAU.
ents.
cm2) Corrosion rate (mm/year) Inhibition efficiency (%)
1 8.7862 3 6.810 102 92.262 5.194 101 94.092 3.406 101 96.123
1.377 102 99.841 2.676 3 8.959 103 99.913 3.438 102 98.714 3.883
103 99.854 2.359 103 99.912 2.570 101 6 4.616 105 99.985 9.176 104
99.645 2.696 104 99.895 6.901 104 99.73
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M. Alam, N.M. Alandis / Industrial Crops and Products 57 (2014)
1728 25
Fig. 7. 1H NMR spectra of CPETAU.
CwmETdCtIcfi
3
fisg
Fig. 11 represents the Tafel plots of bare MS, CPETAU25,PETAU30,
CPETAU35, and CPETAU40 coated in tap water. Tapater contains
chloride ions which frequently show detrimental toetal substrate
(Akram et al., 2014). The observation showed thatcorr (638.42 vs
SCE for MS) showed a positive shift for coated MS.he value of Ecorr
for CPETAU40 was higher than CUPETA25, the Icorrecreased from bare
MS to CPETAU25, CPETAU30, CPETAU35, andPETAU40, respectively. The
corrosion rate for bare MS was foundo be higher than coated CPETAU.
The higher values of Ecorr, lowercorr and corrosion rate confirm
that the polymer film put off toorrosion, it means corrosion ion
did not penetrate the polymericlm of CPETAU.
.5. Thermal analysisDSC thermogram (Fig. 12) of corn oil shows
two endotherms,rst at 27.67 to 2.28 centered at 10.08, second
endothermtarting at 17.6632.25 centered at 24.52. Similarly, DSC
thermo-ram of HECFA also shows two endotherms from 36.36 to
26.97centered at 32.65, second starting from 26.97 to 3.32
cen-tered at 14.63. DSC thermogram (Fig. 13) of CPETAU35
showsendotherm starting at 120 C to 252 C centered at 218 C.
TGAthermogram shows the onset of degradation beyond this
temper-ature. This endothermic peak may be correlated to the
meltingphenomenon.
TGA thermogram (Fig. 14) of CPETA, CPETAU30, CPETAU35
andCPETAU40 reveal 5% weight loss at 250 C, 272 C, 285 C and 286
C,respectively. 10% weight loss in either case is observed at 286
C,317 C, 324 C and 328 C, respectively. In CPETA and CPETAU30,50%
weight loss occurs at 458 C and 476 C, respectively, whilein
CPETAU35 and CPETAU40, for 50% weight loss, the
degradationtemperatures were found to be comparable (overlapping)
as canbe seen in the thermogram, within the temperature range of
471to 475 C. In CPETAU30, CPETAU35, and CPETAU40, these
degra-dation temperatures were observed at higher values compared
to
CPETA. This difference in temperature is attributed to the
presenceof urethane linkages in CPETAU, which confer higher thermal
sta-bility. CPETAU35 and CPETAU40 resins can be safely used up
to250 C.
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26 M. Alam, N.M. Alandis / Industrial Crops and Products 57
(2014) 1728
Fig. 8. 13C NMR spectra of CPETAU.Fig. 9. Tafel plots of CPETAU
coated in 5 wt.% NaCl. Fig. 10. Tafel plots of CPETAU coated in 3.5
wt.% HCl.
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M. Alam, N.M. Alandis / Industrial Crops and Products 57 (2014)
1728 27
Fig. 11. Tafel plots CPETAU coated in tap water.
Fig. 12. DSC thermogram of corn oil and HECFA.
Fig. 13. DSC thermogram of CPETAU35.Fig. 14. TGA thermogram of
CPETA and CPETAU.
4. Conclusions
Corn oil based urethane modified polyetheramide coatingscured at
room temperature and an eco-friendly coating material.A new
combinations properties of amide, ether and urethane couldbe
achieved by this approach. Among all the resins, CPETAU35coatings
showed good scratch hardness, flexibility, gloss and cor-rosion
resistance performance. Thermal analysis reveals CPETAU35can be
safely used up to 250 C. The approach provides an alterna-tive
method to utilization of corn oil.
Acknowledgements
This project was supported by King Saud University, Deanshipof
Scientific Research, College of Science Research Center.
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Corn oil based poly(ether amide urethane) coating
materialSynthesis, characterization and coating properties1
Introduction2 Materials and methods2.1 Synthesis of
N,N-bis(2-hydroxy ethyl) corn oil fatty amide (HECFA)2.2 Synthesis
of polyetheramide (CPETA)2.3 Synthesis of poly(ether amide
urethane) (CPETAU)
3 Results and discussion3.1 Spectral analysis3.1.1 Corn oil3.1.2
HECFA3.1.3 CPETA3.1.4 CPETAU
3.2 Physico-chemical analysis3.3 Physico-mechanical properties
of coating3.4 Corrosion tests3.5 Thermal analysis
4 ConclusionsAcknowledgementsReferences
