RA11-Jatropha Curcas Oil

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Progress in Organic Coatings 74 (2012) 596602

Contents lists available at SciVerse ScienceDirect

Progress in Organic Coatings

journal homepage: www.elsevier .com/ locate /porgcoat

Preparation and characterization ofJatropha Curcas oil based alkyd resin suitable

for surface coating

Monalisha Boruah, Pronob Gogoi, Binoy Adhikari, Swapan Kumar Dolui

Department of Chemical Sciences, TezpurUniversity, Napaam, Assam 784028, India

a r t i c l e i n f o

Article history:

Received18 March2011

Receivedin revised form 13 February 2012Accepted 15 February 2012

Available online 4 March 2012

Keywords:

Jatropha Curcas oil

Alkyd resin

Renewable resources

Surface coating

a b s t r a c t

Jatropha Curcas oil was extracted from Jatropha seeds by solvent extraction method. Three different

alkyd resins have been developed fromJatropha Curcas oil by varying the amount ofphthalic and maleic

anhydride. The prepared resins are cured by using methyl-ethyl ketone peroxide (MEKP) as initiator and

Co-octoate as an accelerator at 120 C. The characterizations ofthe resins for structure establishment is

carried out using Fourier transform infrared (FTIR) and proton nuclear magnetic resonance (1H NMR)

spectroscopic techniques. The concomitant properties of the cured resins such as acid value, saponifi-

cation value, viscosity, molecular weight, etc. are also evaluated by standard methods. The cured resins

have been tested for chemical resistance, pencil hardness, adhesion, thermal stability and gloss and it

can be concluded that the resins may find potential applications in surface coating purposes.

2012 Elsevier B.V. All rights reserved.

1. Introduction

The uses of renewable resources in different fields of applica-

tions of polymers have been proliferating day by day because of

increased worldwide awareness of environmental concerns and

depletion of world oil pool. Naturally renewable resources possess

many advantages such as availability of feedstock, environment

friendly nature and low cost [13]. The vast forest resources and

farm lands in India yield a large variety of oil-bearing seeds. A

numberof seed oils have been used in thesynthesis of various poly-

meric resins like polyester, epoxy, polyurethane, polyester amide,

etc. [1,47]. Major seed oils used traditionally for preparation of

suchresins are linseed, castor, soyabean,sunflower,safflower,tung,

coconut, etc. These resinshave been used in differentfields of appli-

cations such as paint, coating, adhesives, binder for composites,etc.

Non-traditionaloils such as nahar oil, rubberseed oil, jatropha seed

oil, mahua-oil, melon seedoil, annona squmosa, African mahogany

seed oil, African locust bean seed oil, etc. are not exploited much in

the preparation of alkyd resins [1,2,813]. The products based onvegetableoils are developedkeeping twocriteriain mind. First,the

products must meet the technical andindustrial standardsof dura-

bility, fastness to exposure, resistance to chemicals, etc. Secondly,

the products must also meet all ecologically relevant standards

[14].

Dutta et al. synthesized and characterized polyester resin based

on Nahar seed oil. Three different polyester resins were developed

Correspondingauthor. Tel.: +91 9957198489.

E-mail address: [email protected](S.K. Dolui).

froma purified vegetable oil.The performance characteristicsof the

polyester resins were improved by blending with other commer-

cial resins. They also reported the use of these polyester resins as

binder materialfor industrialstoving paint[8]. Guner et al.reported

thepreparation of various polymers fromtriglycerideoils. The pres-

ence of oil/fatty acid chain in the polymer structure improves some

physical properties of polymer in terms of flexibility, adhesion and

resistance to water and chemicals. These polymers were reported

to be biodegradable and biocompatible [15]. Aigbodion et al. stud-

ied the utilization of maleinized rubber seed oil and its alkyd resin

as binders in water-borne coatings. The rubberseed oil was treated

withdifferentamounts of maleic anhydrideand evaluatedas binder

in non-polluting coating and also used to prepare alkyd resin. The

incorporationof maleic anhydrideinto rubber seedoil increases the

acid value and saponification value but decreases the iodine value.

The alkyd films were highly resistant to acid, brine and water but

only fairly resistant to alkali while maleinized rubber seed oil films

exhibited poor chemical resistance [9]. Kumar et al. made anevalu-

ation of Jatropha Curcasas multipurpose oilseed crop forindustrialuses. Jatropha is a drought-resistant shrub or tree, which is widely

distributed in the wildor semi-cultivatedareas in Central andSouth

America, Africa, and South-East Asia [16,17]. The first commercial

applications ofJatropha were reported from Lisbon, where the oil

imported from Cape Verde was used for soap production and for

lamps.The Jatropha oilwas blended with Palmbiodiesel to improve

oxidation stability needed for South Asian and South East-Asian

countries [18]. Akintayo et al. studied the Characteristics and com-

position of Jatropha Curcas oils and cakes. From their study, the

fatty acid composition of Jatropha Curcas oilwas foundas: palmitic

acid, 19.9%, stearic acid, 6.8%, oleic acid, 41.3%, linoleic acid, 31.4%,

0300-9440/$ seefrontmatter 2012 Elsevier B.V. All rights reserved.

doi:10.1016/j.porgcoat.2012.02.007
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M. Boruah et al. / Progress in Organic Coatings 74 (2012) 596602 597

linolenic acid,3.0%, saturatedacids, 26.3%, unsaturated acids, 72.7%,

etc. [19]. Odetoye et al. reported the utilization of Jatropha Cur-

cas Linnaeus (JCL) seed oil in the preparation of four sets of alkyd

resin (35%, 50%, 60% and 75% oil formulations) using a two-stage

alcoholysispolyesterification method. The alkyds were tested for

solubility, viscosity, colour, drying performance, solidification time

and film characteristics,e.g. thickness, hardness, adhesion and flex-

ibility, etc. They also evaluated the properties of the alkyds and

compared the properties with those of the commercial standards

[20].

Jatropha Curcas is a versatile plant with several and poten-

tial uses such as biodiesel, medicine, cosmetics, etc. This oil has

also been used for making soap commercially in many countries.

In addition, several parts of the Jatropha plant have medical and

cosmetic uses [21]. Jatropha Curcas is becoming the future source

of biodiesel for India and other countries. Among the various oil

seeds, Jatropha Curcas has been found more suitable for biodiesel

production on the basis of various characteristics. The cultivation

of Jatropha is possible under stress condition and the oil of these

species having various characteristics is more suitable for biodiesel

production [22]. Different stages of Jatropha seeds are shown in

Fig. 1.

It has been found from these analyses that although Jatropha

Curcas oil is exploited for different potential applications, it has

not yet attracted much interest in surface coating industries. In

this paper, an attempt has been made to synthesize alkyd resins of

different compositions from Jatropha Curcas oil. Physico-chemical

properties of alkyd resins are evaluated to assess the suitability of

Jatropha oil as potential raw material for the preparation of alkyd

resin.

2. Experimental

2.1. Materials

Phthalic anhydride (Aldrich), maleic anhydride (Aldrich) and

lead monoxide (S.D. Fine Chem. Ltd.) were commercial grade

reagent and used without further purification. Methyl-ethyl ketone

peroxide and cobalt-octoate (Aldrich), glycerol and phenolph-

thalein (Qualigen fine chemicals) were used as received. All the

solvents were purified before using by standard method. Jatropha

seed was collected from Sonitpur, Assam (India) and the oil was

collected from the seeds by solvent extraction method. The purifi-

cation was done by alkali refining technique.

2.2. Instruments and methods

The FT-IR spectra of the resins were recorded by FT-IR Nico-

let 410 using KBr pellet. 1

H NMR spectra were obtained by JEOL400MHz NMRspectrometer using CDCl3 as the solvent. The ther-

mogravimetric analysis was done with the thermogravimetric

analyser TGA-50, Shimadzu at the heating rate of 10C/min under

N2 atmosphere. The pencil hardness was determined in scale of

6B to 6H of a standard set of pencils by dragging the pencil along

the films using a pencil hardness tester. The relative amount of

scratching is reported as the pencil number which offers the least

scratching. Gloss was determined by using a 60 Gloss meter.

Viscosity was determined by Brookfield viscometer, RVT model

(#spindle 3, RPM 20) at room temperature .The physical proper-

ties of the resins such as acid value, saponification value, drying

time and adhesion were determined by standard methods [23].

Also, molecular weight of the oil and resins were determined by

GPC technique.

Table 1

Compositions of the prepared resins.

Resins Compositions Oil (g) MA (g) PA (g) Glycerol (g)

Resin 1 100% PA 32.68 0 17.774 9.34

Resin 2 50% PA & 50% MA 32.68 5.883 8.887 9.34

Resin 3 75% M A & 25% PA 32.68 8.825 4.443 9.34

2.3. Synthesis of alkyd resin from Jatropha Curcas oil

A three necked round bottom flask equipped with a mechan-

ical stirrer, a thermometer and a nitrogen gas inlet was charged

with 32.68g (0.04 mol) of Jatropha Curcas oil, 7.36g (0.08mol) of

glycerol and 0.05 weight percent (with respect to the oil) of PbO

with continuous stirring. The mixture was heated continuously

up to (225230) C for 4560min until it formed monoglyceride,

confirmed by solubility in methanol (resin:methanol = 1:3, v/v) at

ambient temperature. Then the reaction mixture was cooled to

125 C and 0.12mole of acid anhydride in the form of fine powder

with 1.98g of excess glycerol (27%) was added. Now, the reaction

temperature was raised to 230C until it reached acid value in the

range of 2030. The compositions of the three different resins are

shown in Table 1.

2.4. Curing of alkyd resins

The synthesized resins were cured employing the processes

mentionedherein. 1 g of each batch of resin wastakenin a petridish

and mixed with 0.04g of MEKP an initiator (4phr) and 0.02g of

cobalt-octoate as accelerator and after 10min of continuous mix-

ing it was uniformly coated over glass plates and heated at 80C in

oven and further the temperature was increased to 120 C. At dif-

ferenttime interval,the filmwas taken outof the oven andchecked

for hardening of the resin on pressing by finger tip. The curing time

of the resins are shown in Table 3.

2.5. Chemical resistance

A fixed amount of these resins 0.5 g were coated on glass plates

and kept in 250 mLbeakers containing 200mLof different chemi-

cals, viz. 10% aqueous hydrochloric acid (v/v) solution, 1% aqueous

sodium hydroxide (w/v) solution, 10% aqueous sodium chloride

solution and distilled water for 3 days at room temperature.

3. Results and discussion

3.1. Synthesis of alkyd resin from Jatropha Curcas oil

The alkyd resins were synthesized by employing commonly

used alcoholysis process where raw vegetable oil undergoes trans-

esterification when heated with glycerol at 220 C resulting in a

Table 2

Characteristic peaks in FT-IR spectra of resins.

Absorption bands (cm1 ) Functional groups

34663477 O H stretching vibration

2925 Unsaturated C H stretching vibration

2856 CH2asymmetric and symmetric

vibration

17311733 C O stretching vibration

15891647 C C stretching vibration of C C

aliphatic and C C aromatic band

11281165 a nd 1 2691279 C O C s tretching v ibrations a ttached

with aliphatic and aromatic moiety

983985 C C stretching vibration

726743 Out of plane aromatic C H bending

vibration


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598 M. Boruahet al./ Progress in Organic Coatings 74 (2012) 596602

Fig. 1. Jatropha Curcas seeds at different stages: (a) Jatropha Curcas plant with fruits, (b) ripe Jatropha fruits and (c) dry Jatropha seeds.

mixture of mono and diglyceride oil. Then esterification was car-

ried out with the addition of phthalic acid or maleic anhydride at

210 C. Lead monoxide (PbO) is used as catalyst during thereaction.

Scheme 1 represents the general reactions involved in synthesis ofalkyd resins.

This resinification reaction is free from theuse of anysolventsto

shun certain limitations associatedwith it like removal, health haz-

ards, flammability, etc. Nitrogen gas was used as the inert blanket,

which facilitates the removal of water produced during conden-

sation reaction in the second step. The extent of reaction was

monitored by measuring the acid value at different intervals of

time. The reaction was stopped as soon as the desired level of acid

value was attained (Table 4).

3.2. Spectroscopic analysis of resins

The alkyd resins of different compositions were characterized

using FT-IR,1

H NMRspectroscopic techniques.The FT-IR spectrum of the oil is shown in Fig. 2. Characteristic

peaks are found at 3468cm1 due to O H stretching vibration and

at 28562924cm1 is due to aliphatic C H stretching vibration.

Peaks for C O stretching vibration of triglyceride ester appears at

1744cm1, for C C stretching vibration at 1655cm1 and that for

C H bending vibration is found at1456cm1. Also, peakat 1162is

Fig. 2. FT-IR spectrum of theoil.

dueto C O C stretching vibration ofester andthatat 719cm1 is

due to the methylene rocking vibration.

TheFT-IRspectraldata(Fig. 3) of theresins indicate thepresence

of important linkages, viz. ester group, olefinic double bonds andothercharacteristicpeaks as listed in Table 2. The polyesterification

reaction is confirmed by FT-IR analysis. In Jatropha oil, the peak for

>C O band appears at 1744 cm1, whereas in case of synthesized

resins, peaks for >C O bandappear at17311733cm1, indicating

some modification around the carbonyl group. IR absorption peak

forunsaturation offattyacidappearsat 1589cm1 and for aromatic

unsaturation at 1590 cm1. The characteristics peaks of the resins

are shown in Table 2.1H NMRspectrum of the oil has been shown in Fig. 4. Peaks at

0.870.89 ppm are due to the protons of terminal methyl group.

For all the protons of internal CH2 groups present in the fatty

acid chain peaks arise at 1.60ppm. Characteristic peaks at

2.012.05ppm are for allylic protons of CH2, at 2.302.32ppm

Fig. 3. FT-IR spectra of resins (a) Resin 1, (b) Resin 2 and (c) Resin 3.


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Scheme 1. Step 1: Schematic route of formationof mono- anddi-glycerides. Step 2: Schematic route of formation of alkyd resin.

for -protons of ester groups and at 2.752.78 ppm for CH2 of

double allylic protons. Peaks at 4.154.28 ppm are for protons of

glyceride moiety and 5.325.35 ppm are for the protons of the

CH CH moiety.

1H NMRspectra of the resins are shown in Figs. 57 which sup-

port the proposed structure. Peaks at 0.850.89 ppm appear for

the protons of terminal methyl group of the fatty acid chains and

that at 1.60 ppm may be due to protons of CH2group attached

Table 3

Curingtimes of theresins.

Curing time (h) Resin 1 Resin 2 Resin 3

Jatropha Curcas oil based alkyd resins 9 h at 120 C 6 h at 120 C 4 h at 120 C

Nahar oil based alkyd resins 9 h at 175 C 7 h at 150 C 6 h at 150 C


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Table 4

Physical properties of Jatropha oil based alkyd resins.

Serial no. Properties Resin 1 Resin 2 Resin 3

1 Acid value (mg of KOH/g) 23 25 44

2 Saponification value (mg KOH/g) 383 392 399

3 Viscosity (centipoise) 33 45 65

4 Volatile matter (%) 3.25 3.80 4.18

5 Physical appearance Dark brown Dark brown Dark brown

Transparent Transparent Transparent

Fig. 4. 1H NMRspectrum of theoil.

Fig. 5. 1H NMRspectrum of Resin 1.

Fig. 6. 1H NMRspectrum of Resin 2.

next to the above terminal methyl group. Peaks at 1.211.29ppm

are observed for protons of all the internal CH2 groups present

in the fatty acid chain. For protons of unsaturated carbons, the

characteristic peaks appear at 5.335.35 ppm and the same for

methyleneprotonsof glycerol moiety arefound at3.544.79ppm.

The protons for CH ofsame glycerolmoiety are observedat very

high value of 6.286.86 ppm. It may be due to the deshielding

effect by the anhydride group possessing one unsaturation unit

(MA) or aromatic ring (PA) which are absent in the1 H NMRspec-

trum of the oil. The PA containing resin (Resin 1) shows aromatic

protons at 7.547.83.

3.3. Curing of alkyd resin

The curing times of synthesized resins are listed in Table 3. The

curing time decreases continuously with the increase of MA con-

tent in resins. Resin 3 shows the lowest curing time (4h at 120C)

whereas the curing time for Resin 1 is 9 h and that for Resin 2 is

6h at same temperature. This may be due to the fact that with

the increase of MA content in resin, the degree of unsaturation

increases, which causes decrease in the curing time. The unsatura-

tion is the main component forcrosslinking reaction by free radical

mechanism [24].

Nahar oil based alkyd resins, which have already been used in

various paint industries, show similar curing time. PA (100%) con-

taining resin shows the highest curing time (9h at 175 C) and it

tends to decrease with increase of MA. At same temperature, 50%PA & 50% MA containing resin shows curing time 7 h and 25% PA &

75% MA containing resin shows curing time 6 h [8].

3.4. Physical properties of resins

The physical properties of the alkyd resins are given in Table 4.

The acid value increases from 23 to 44 with increase in MA

Fig. 7. 1

H NMRspectrum of Resin 3.


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Table 5

Molecularweights and polydispersity index of theoil and resins.

Sample Numberaverage

molecular weight (Mn)

Weight average

molecular weight (Mw)

Polydispersity

index (PDI)

Oil 1457 1512 1.03

Resin 1 1504 1736 1.15

Resin 2 1 716 2043 1.09

Resin 3 1 919 2590 1.34

content. The resinification reaction was deliberately stopped at ear-

lier stage to avoid undesirable gel formation. The moderate acid

values of all synthesized resins support their moderate reactivity

for surface coating applications. The saponification values of the

resins are found to be in the range 383399. The saponification

value decreases as the amount of phthalic anhydride decreases.

Resin 3 exhibits the maximum viscosity. The viscosity tends to

increase as the amount of maleic anhydride content increases due

to highermolecular weightof theresin. Theamount of volatile mat-

teris low(3.254.18) forall theresins andhencethe resinsmay find

suitability in non-polluting coating applications [9]. The molecu-

lar weights (Mw) and polydispersity index of the oil and resin are

given in Table 5. In case ofthe resins, theMw tends to increase with

increase in MA content.

3.5. Physical properties of the cured alkyd resins

Physical properties of the cured films are given in Table 6.The

pencil hardness value is the highest for the Resin 1 with phthalic

anhydridedue to the presence of rigid aromatic moietyin the poly-

mer chain [24,25]. The adhesion characteristics of all the resins are

very good due to the presence of polar ester bonds [3]. The gloss

property of the resins is also found to be good. These results indi-

cate the potential of these resins for surface coating applications

[26].

For comparison, the physical properties of the cured films of

Nahar oil based alkyd resins are given in Table 6 [8]. It can be seen

that theperformance of the cured resinsof both the oils are similar.

3.6. Chemical resistance

The performance properties of cured resins under different

chemical environments are given in Table 7. For this, equal amount

of each cured film was dipped into the solvents and after a fixed

time period, weight loss was measured. More the weight loss, less

the resin is resistant to the respective solvent and vice versa.

Fig. 8. TGA thermogramof resins: (a) Resin 1, (b) Resin 2 and (c) Resin 3.

It was found that resins are highly resistant to dilute HCl, aque-

ous NaCl solution and distilled water. Resin 1, based on phthalic

anhydride is fairlyresistantto alkali, which may be dueto the pres-ence of rigid aromatic moiety. Butresinswith maleic anhydride are

notso resistantto alkali. This poor alkaliresistanceof theresins may

be due to the presence of alkali hydrolysable ester group [3].

The performance properties of Nahar oil based alkyd resins

under different chemical environments are given in Table 7 [8].

Chemical resistances of both types of resins are found to be similar.

3.7. Thermal analysis

The thermostability of the cured resins has been studied by

thermogravimetric analysis (TGA) under N2 atmosphere. The TGA

traces of the cured resins are given in Fig. 8. The initial 12% weight

loss is attributed to the loss of moisture. This has been confirmed

from the isothermal heating of polymers at 150 C for 12h, whichindicates a same amount of weight loss without any change in

chemical structure as confirmed by FT-IR spectroscopy. The initial

decomposition of all the resins approximately starts at 330C. The

overall thermal stabilityof theresins arein theorderResin3 > Resin

2 > Resin 1 (Fig. 8). The high MA content in Resin 3 causes increase

in crosslinking density thereby improving the thermostability of

the cured resins. However, the amount of residue at 600 C is very

Table 6

The pencil hardness, adhesion and gloss characteristics of the cured resins.

Alkyd type Resins Pencil hardness Adhesion (100%) Gloss (60)

Resin 1 H 100 85

Jatropha Curcas oil based Resin 2 2B 100 80

Resin 3 HB 100 77

Resin 1 H 100 85

Nahar oil based Resin 2 HB 100 81

Resin 3 2B 100 70

Table 7

Chemical resistance of the alkyd resins.

Alkyd type Resins 10%HCl (aq) 1%NaOH (aq) 10% NaCl (aq) Distilled water

Resin 1 Excellent Fair Excellent Excellent

Jatropha Curcas oil based Resin 2 Excellent Poor Excellent Excellent

Resin 3 Excellent Poor Excellent Excellent

Resin 1 Excellent Fair Excellent Excellent

Nahar oil based Resin 2 Excellent Poor Excellent Excellent

Resin 3 Excellent Poor Excellent Excellent


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low and almost equivalent for all the resins. Thus, Jatropha Curcas

oil modified polyester resins bear very good thermostability under

the nitrogen atmosphere.

4. Conclusion

In conclusion, alkyd resins based on renewable Jatropha Curcas

oiland containing mixtures of maleicanhydride andphthalicanhy-

dride in differentrations have been successfullysynthesized. It wasfound that theamount ofmaleic anhydrideused plays an important

role in tuning the properties of these resins. The structures of the

resins are confirmed by FT-IR and1 H NMRspectra. The resins pos-

sess gratifying gloss, hardness, adhesion and chemical resistance

properties, which make them suitable for surface coating, binder

for composite, etc. Moreover, the thermostability of the resins is

quite high and the initial decomposition of these resins does not

occur until at nearly 330 C. This study reveals that Jatropha Cur-

cas oil can potentially be used as a raw material for the coatings

industry.

Acknowledgement

The authors express their gratitude and thanks to the authority

of Tezpur University for providing facilities to carry out this work.

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RA11-Jatropha Curcas Oil