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Polyesteramide Urethane and Alumina-Filled Coating Characterization, Notas de estudo de Engenharia de Produção

Universidade de Araraquara (UNIARA)Engenharia de Produção

An explanation for the changes in scratch hardness, impact resistance, flexibility, and chemical resistance of polyesteramide and alumina-filled polyesteramide coatings with the addition of tdi. The synthesis, preparation, and testing of these coatings are discussed, along with the comparison of their ftir and 1h–nmr spectra. The physicochemical characteristics of peau and apeau are also presented.

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StudiesonUrethane-ModifiedAlumina-Filled
PolyesteramideAnticorrosiveCoatingsCuredatAmbient
Temperature
SHARIFAHMAD,S.M.ASHRAF,ABULHASNAT,S.YADAV,A.JAMAL
MaterialsResearchLaboratory,DepartmentofChemistryJamiaMilliaIslamia,NewDelhi110025,India
Received14July2000;accepted11December2000
Publishedonline10September2001;DOI10.1002/app.2029
ABSTRACT: Coatingspreparedfrompolyesteramideresinsynthesizedfromlinseedoil,
arenewableresource,havebeenfoundtoshowimprovedphysicomechanicaland
anticorrosivecharacteristics.Thesepropertiesarefurtherimprovedwhenaluminumis
incorporatedinthepolyesteramideresin.Thecoatingsofthisresinaregenerally
obtainedbybakingatelevatedtemperatures.Withaviewtowardtheuseoflinseedoil,
asaprecursorforthesynthesisofpolyesteramideresinsandtocuretheircoatingsat
ambienttemperature,toluylenediisocyanate(TDI)wasincorporatedintopolyesteram-
ideandalumina-filledpolyesteramideinvaryingproportionstoobtainurethane-mod-
ifiedresins.Thelatterresinswerefoundtocureatroomtemperature.Thebroad
structuralfeaturesoftheurethane-modifiedpolyesteramideandalumina-filledpoly-
esteramidewereconfirmedbyFTIRand
1
H–NMRspectroscopies.Scratchhardness;
impactresistance;bendingresistance;speculargloss;andresistancetoacid,alkali,and
organicsolventsofthecoatingsoftheseresinsweredeterminedbystandardmethods.
Physicomechanicalandanticorrosiveproperties,speculargloss,andthermalstability
oftheurethane-modifiedalumina-filledpolyesteramidecoatingswerefoundtobeat
higherlevelsamongtheseresins.ItwasfoundthatTDIcouldbeincorporatedin
polyesteramideuptoonly6wt%,suchthatabovethisloadingitspropertiesstartedto
deteriorate,whereasalumina-filledpolyesteramidecouldtakeupto10wt%TDI.
Explanationisprovidedfortheincreaseinscratchhardnessandimpactresistance
above6and10wt%additionofTDIinpolyesteramideandalumina-filledpolyester-
amide,respectively,aswellasforthedecreaseinflexibilityandresistancetosolvents,
acid,andalkaliofcoatingsoftheseresinsabovetheselimitsofTDIaddition.©2001John
Wiley&Sons,Inc.JApplPolymSci82:1855–1865,2001
Keywords:coatings;polyesteramide;alumina;urethane;curing
INTRODUCTION
Polyesteramideresinsareamide-modifiedalkyds
thathaveimprovedcharacteristicsovernormal
alkydsintermsofhardness,easeofdrying,and
watervaporresistance.
1–3
Generally,polyesteram-
idecoatingsareobtainedbybakingatandabove
175°C.
4,5
Toimprovethephysicomechanicaland
anticorrosivecharacteristicsofbakedcoatings,we
incorporatedaluminuminthebackboneofthepoly-
mer.
6
Wefoundthattheaforementionedproperties
ofthecoatingswereenhancedappreciablyinthe
caseofalumina-filledpolyesteramides.
6
Curingof
thepolyesteramideatelevatedtemperatureisa
multistepprocessandisalsoenergyconsuming.It
is,therefore,desirabletodevelopasimplecuring
routeoperativeatambienttemperaturetoproduce
Correspondenceto:S.Ahmad([email protected]).
Contractgrantsponsor:ARDB(MinistryofDefense,In-
dia);contractgrantnumber:Aero/RD-134/110/106/934.
JournalofAppliedPolymerScience,Vol.82,1855–1865(2001)
©2001JohnWiley&Sons,Inc.
1855
pf3
pf4
pf5
pf8
pf9
pfa

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Studies on Urethane-Modified Alumina-Filled

Polyesteramide Anticorrosive Coatings Cured at Ambient

Temperature

SHARIF AHMAD, S. M. ASHRAF, ABUL HASNAT, S. YADAV, A. JAMAL

Materials Research Laboratory, Department of Chemistry Jamia Millia Islamia, New Delhi 110 025, India

Received 14 July 2000; accepted 11 December 2000 Published online 10 September 2001; DOI 10.1002/app.

ABSTRACT: Coatings prepared from polyesteramide resin synthesized from linseed oil, a renewable resource, have been found to show improved physicomechanical and anticorrosive characteristics. These properties are further improved when aluminum is incorporated in the polyesteramide resin. The coatings of this resin are generally obtained by baking at elevated temperatures. With a view toward the use of linseed oil, as a precursor for the synthesis of polyesteramide resins and to cure their coatings at ambient temperature, toluylene diisocyanate (TDI) was incorporated into polyesteram- ide and alumina-filled polyesteramide in varying proportions to obtain urethane-mod- ified resins. The latter resins were found to cure at room temperature. The broad structural features of the urethane-modified polyesteramide and alumina-filled poly- esteramide were confirmed by FTIR and 1 H–NMR spectroscopies. Scratch hardness; impact resistance; bending resistance; specular gloss; and resistance to acid, alkali, and organic solvents of the coatings of these resins were determined by standard methods. Physicomechanical and anticorrosive properties, specular gloss, and thermal stability of the urethane-modified alumina-filled polyesteramide coatings were found to be at higher levels among these resins. It was found that TDI could be incorporated in polyesteramide up to only 6 wt %, such that above this loading its properties started to deteriorate, whereas alumina-filled polyesteramide could take up to 10 wt % TDI. Explanation is provided for the increase in scratch hardness and impact resistance above 6 and 10 wt % addition of TDI in polyesteramide and alumina-filled polyester- amide, respectively, as well as for the decrease in flexibility and resistance to solvents, acid, and alkali of coatings of these resins above these limits of TDI addition. © 2001 John Wiley & Sons, Inc. J Appl Polym Sci 82: 1855–1865, 2001

Key words: coatings; polyesteramide; alumina; urethane; curing

INTRODUCTION

Polyesteramide resins are amide-modified alkyds

that have improved characteristics over normal

alkyds in terms of hardness, ease of drying, and

water vapor resistance.1–3^ Generally, polyesteram-

ide coatings are obtained by baking at and above

175°C.4,5^ To improve the physicomechanical and

anticorrosive characteristics of baked coatings, we

incorporated aluminum in the backbone of the poly-

mer.^6 We found that the aforementioned properties

of the coatings were enhanced appreciably in the

case of alumina-filled polyesteramides.^6 Curing of

the polyesteramide at elevated temperature is a

multistep process and is also energy consuming. It

is, therefore, desirable to develop a simple curing

route operative at ambient temperature to produce

Correspondence to: S. Ahmad ([email protected]). Contract grant sponsor: ARDB (Ministry of Defense, In- dia); contract grant number: Aero/RD-134/110/106/934. Journal of Applied Polymer Science, Vol. 82, 1855–1865 (2001) © 2001 John Wiley & Sons, Inc.

1855

coatings of improved physicomechanical and anti-

corrosive properties compared to high-temperature

baked coatings of polyesteramide and alumina-

filled polyesteramide. It was previously reported

that toluylene diisocyanate (TDI) can be used for

curing aromatic polyesteramide at room tempera-

ture.7,

The presence of a urethane linkage in the poly-

esteramide has been found to considerably en-

hance the performance of these coatings in terms

of adhesion, toughness, weather resistance, and

chemical/solvent resistance.^9 Polyurethane resins

as a class are well recognized for their excellent

adhesion, ambient-temperature curing, flexibil-

ity, weather resistance, and resistance to solvent

and chemical attack.^10 In our earlier work we

attempted to prepare alumina-filled polyesteram-

ide from linseed oil, used as a precursor of renew-

able nature. In this work we have attempted to

obtain urethane-modified polyesteramide using

TDI with the double objective of using a precursor

obtained from a renewable resource and of en-

hancing the physicomechanical and anticorrosive

properties of the coatings of these resins through

curing at room temperature. A survey of the lit-

erature reveals that modifications of polyesteram-

ide by butylated melamine formaldehyde,^11 sty-

rene,^12 and also by metals^6 have been attempted.

However, no work has been reported on the mod-

ification of alumina-filled polyesteramide synthe-

sized from a vegetable oil by urethane.13–15^ We

report our findings on the above investigations in

this communication.

EXPERIMENTAL

Materials

Oil was extracted from linseed (procured from a

local market) through Soxhlet apparatus. Petro-

leum ether was used as a solvent. The fatty acid

composition of the oil was determined by gas chro-

matography (GC; 111/8 s.s. column, FID detector)

(Table I). Phthalic acid, sodium methoxide, alu-

minum hydroxide, xylene, toluylene-2,4 diisocya-

nate (Merck, India and Germany), and diethanol-

amine (S.D. Fine Chemicals, India) were of ana-

lytical grade.

Synthesis

Synthesis of Polyesteramide (PEA) and Alumina-

Filled Polyesteramide (APEA)

PEA and APEA were prepared according to a

previously reported method.^6

Synthesis of Urethane-Modified Polyesteramide

(PEAU) and Alumina-Filled Polyesteramide

(APEAU)

Polyesteramide and alumina-filled polyesteram-

ide were dissolved in xylene and treated with

varying amounts of toluylene-2,4 diisocyanate in

a four-neck round-bottom flask fitted with a ni-

trogen inlet, a thermometer, and a stirrer. The

extents of loading of TDI (in wt %) in PEA and

APEA are provided in Table II. The reaction was

carried out under stirring at 145 6 5°C. The

progress of the reaction was monitored by thin

layer chromatography (TLC) as well as by hy-

droxyl value determination. The solvent was re-

moved from PEAU and APEAU in a rotatory vac-

uum evaporator.

Characterization

PEAU and APEAU were characterized by FTIR

and 1 H–NMR spectroscopies. FTIR spectra of

these polymers were taken on Perkin–Elmer 1750

FTIR spectrophotometer (Perkin Elmer Cetus In-

Table I Characterization of Oil, HELA, PEA, and APEA

Characteristic Linseed Oil HELA PEA APEA

Acid value (mg KOH) 8.3 — 7.0 6. Hydroxyl value (%) 0.3 — 7.87 14. Saponification value 160 136 128 118 Iodine value 181 86 48 20 Specific gravity 0.896 0.926 0.938 0. Refractive index 1.478 1.497 1.507 1. Inherent viscosity (dL/g) — — 0.652 0. Linoleic acid (%) 14 — — — Linolenic acid (%) 44 — — — Oleic acid (%) 20 — — —

1856 AHMAD ET AL.

OH group of carboxyl on interaction with

Al(OH) 3. The above observation confirms the in-

corporation of alumina in APEA. The 1 H–NMR

peak of the CH 2 group adjacent to ester in PEA is

sharp and pronounced ( d 2.0 ppm). This peak is

suppressed and shifted slightly downfield ( d

2.29 –2.30 ppm) in APEA because of the presence

of aluminum in the chain. The peak for CH 2 at-

tached to amide is observed at d 1.58 ppm in PEA

as well as in APEA. The peak for the aliphatic

chain is observed at d 1.29 ppm for PEA. In the

case of APEA it is present at d 1.25 ppm. These

observations broadly confirm the structures of

PEA and APEA, as shown in Figure 5(a) and (b).

Comparison of PEA and PEAU Structures

Spectra for PEAU are more spread than those for

PEA in the range of 3500–3150 cm^21 , showing the

overlap of OH and NH groups. In the case of PEA

the peak is suppressed and appears as a shoulder at

3460 cm^21 , indicating the presence of the OH group

only. In PEAU, the NH deformation mode appears

at 1557 cm^21. In addition to the terminal methyl

group peak of aliphatic chain at d 0.9 ppm, 1 H–

NMR spectra of PEAU show the presence of the

methyl group of TDI at d 2.1–2.24 ppm. The pres-

ence of CAO of ester, CON, benzene ring, and

aliphatic chain are confirmed by the appearance of

their peaks in the spectra (Table IV). These obser-

vations broadly confirm the structures of PEA and

PEAU, proposed in Figure 5(a) and (c), respectively.

The peak of carboxyl OH at d 7.9 ppm in PEA does

not appear in PEAU. This also verifies the interac-

tion of TDI with carboxyl-terminated PEA and dis-

appearance of the carboxyl group.^16

Comparison of APEA and APEAU Structures

Perusal of Table IV reveals that APEA shows a

broad peak spread between 3650 and 3120 cm^21

(centered at 3455 cm^21 ). APEAU shows well-re-

solved peaks in this range at 3600, 3460, 3300,

and 3150 cm^21. The broadness in the APEA peak

may be attributed to the presence of alcoholic OH

and OH attached to aluminum. NH stretching

peak of the urethane group in APEAU appears at

3460 and 3300 cm^21. The CAO peak in APEA

appears at 1760 cm^21 , whereas in APEAU this

peak shows at 1727 cm^21. The CAO peaks in

PEAU (1724 cm^21 ) and in APEAU (1727 cm^21 )

could be related to the presence of the urethane

group in the chain. We also notice that the 1 H–

Table III NMR peak of CAO in APEAU is shifted upfield

Film Properties of Ambient Cured Polyesteramide Urethane and Alumina-Filled Polyesteramide Urethane

ResinCode

Drying Time

(min)

ScratchHardness

(kg)

Impact Resistance

[lbs/in.(passes)]

Glossat 60°C

Bending

Corrosion Resistance

a

Dry toTouch

Dry toHard

H

O 2

(10 days)

NaOH (5%) (3 h)

HCl (5%)(10 days)

NaCl (3.5%)

(10 days)

Xylene(10 days)

PEAU-

Passes

b^

d^

a^

b^

a^

c

PEAU-

Passes

e^

a^

c^

c^

e

PEAU-

Passes

e^

a^

c^

c^

e

PEAU-

Fails

e^

a^

c^

c^

e

APEAU-

Passes

e^

a^

c^

c^

e

APEAU-

Passes

e^

b^

e^

d^

e

APEAU-

Passes

e^

c^

e^

d^

e

APEAU-

Passes

e^

c^

e^

d^

e

APEAU-

Passes

e^

c^

e^

d^

e

a^

a^

5

film completely removed; b

5

film cracked and partially removed; c

5

loss in gloss; d

5

slight loss in gloss; e

5

unaffected.

b^

Passes

5

coatings adhesion test shows on visible damage.

1858 AHMAD ET AL.

(from d 2.3 to d 2.28 –2.31 ppm). This trend is

similar to that for the CAO peak in IR spectra of

the two polymers. We also find that this peak in

APEA is suppressed, whereas in APEAU it is

highly pronounced. The intensity of this peak in

PEAU and APEAU is almost similar to, but much

higher than, that in APEA. These features may be

ascribed to the presence of the urethane CAO

group. In 1 H–NMR spectra of APEAU we observe

a peak at d 2.61–2.65 ppm as in PEAU. This peak

is not observed either in PEA or APEA. We at-

tribute this peak to CH 2 adjacent to the urethane

carbonyl group. We also observed the IR peaks for

the benzene ring, CON group, COOOC group,

and the 1 H–NMR peaks of the aliphatic chain,

terminal methyl group of the aliphatic chain, and

methyl group of TDI (Table IV). These observa-

tions broadly confirm the proposed structure of

APEAU as given in Figure 5(d).

Physicochemical Characteristics of PEAU and

APEAU

Tables I and II give the values of some physical

and chemical characteristics of PEAU and

APEAU along with those of PEA and APEA. We

notice that on incorporation of TDI the acid value,

hydroxyl value, saponification value, and iodine

value all decrease from the respective values in

PEA and APEA. This indicates the increase in

molar mass on incorporation of TDI in PEA and

APEA. The increase in molar mass is also ob-

served from the increase in values of viscosity and

specific gravity of PEAU and APEAU. Table II

also shows the values of physical and chemical

Figure 1 FT-IR of PEA (– – –) and APEA (——).

Figure 2 FT-IR of PEAU (– – –) and APEAU (——).

POLYESTERAMIDE ANTICORROSIVE COATINGS 1859

little secondary reaction of TDI with urethane

groups present on polymer chains. It is worth men-

tioning that the APEAU does not form lumpy ag-

gregates, indicating that network formation and ge-

lation do not occur in this case, even above 10 wt %

addition of TDI, although only its viscosity in-

creases to the extent of loss of flow property.

When left at room temperature PEAU coatings

will be cured through the secondary reaction of

the moisture with the terminal NCO groups on

PEAU polymeric chains18,19^ (ASTM type 2).

It has been observed that scratch hardness of

PEAU coatings increases even above 6 wt % load-

ing of TDI. However, above this loading the coat-

ings fail the bending test; even chemical proper-

ties of the coatings improve only up to 6 wt %

loading of TDI, beyond which concentration dete-

rioration is noticed, such that the coatings are

increasingly subject to chemical attack.

The scratch hardness depends on the cohesive

force between the polymer chains and, hence, as the

size of the PEAU chains increases, the cohesive

force between the PEAU polymeric chains also in-

creases, thus enhancing the scratch hardness of the

coatings with the increased loading of TDI. Beyond

6 wt % addition of TDI, although the size of the

polymer chain still increases, thus generating an

increase in scratch hardness, because of the second-

ary reaction of TDI with the amide groups present

on PEAU chains additional crosslinks start to form

between the neighboring polymeric chain apart

from terminal crosslinks formed between the neigh-

boring chains through moisture curing.^18 The addi-

tional crosslinks formed through amide groups pro-

duce stiffening in the chains, which not only causes

the coatings to fail the bending test but also lowers

the chemical resistance of these coatings, as has

been observed (Table III).

In the case of APEAU we notice the same ef-

fect, that viscosity, scratch hardness, impact re-

sistant, and flexibility all increase with the in-

creased loading of TDI. In this case we found that

these properties were higher than those in PEAU.

This may essentially be ascribed to the higher

molar mass and higher chain length of APEAU,

as exhibited by higher viscosity and specific grav-

ity of APEAU condensates.

We have observed that immobility of APEAU

condensate above 10 wt % loading of TDI makes it

unbrushable. It is interesting to note in this case

that, although the viscosity of APEAU condensate

at this loading of TDI is extremely high, no lumpy

Figure 4^1 H-NMR spectra of APEAU.

POLYESTERAMIDE ANTICORROSIVE COATINGS 1861

aggregate formation (gelation) occurs, unlike in

the case of PEAU. We presume that because of

the presence of only the urethane group in the

polymer chains, the secondary reaction of TDI

with this group is negligible,^17 resulting in non-

formation of crosslinks with the urethane groups

present on the polymeric chains; thus gelation of

the condensate does not occur as in the case of

PEAU. On curing of APEAU resins the crosslinks

between the polymer chain will be found only at

the terminal isocyanate groups of the polymeric

chains initiated by reaction with moisture.^18 Be-

cause of this behavior coatings of APEAU resin

will be more flexible. We have actually observed

that APEAU coatings pass the bending test up to

10 wt % loading of TDI. The improved resistivity

of these coating to chemical attack can also be

attributed to lesser stiffness or stresses in these

films because of higher flexibility.

Specular Gloss of PEAU and APEAU Coatings

Table V shows the values of gloss of PEAU and

APEAU coatings with 6 wt % loading of TDI at

various temperatures. We notice that at ambient

Figure 5 (a) Synthesis of polyesteramide (PEA); (b) synthesis of alumina filled poly- esteramide (PEA); (c) synthesis of polyesteramide urethane (PEAU); (d) synthesis of alumina filled polyesteramide urethane (APEAU).

1862 AHMAD ET AL.

Table IV

FTIR and

(^1) H–NMR Values for Polymeric Resins

Functional

Group

PEA

PEAU

APEA

APEAU

IR (cm

2

1 H–NMR

(PPM)

IR (cm

2

1 H–NMR

(PPM)

IR (cm

2

1 H–NMR

(PPM)

IR (cm

21

1 H–NMR

(PPM)

OH (alcoholic)

3460 (shoulder)

d^

centeredat 3285

d^

d^

5.3 (higherintensity)

d^

OH (carboxyl)

d^

N

O

H

(deformation)

C

A

O (ester)

d^

2.3 (CH

2

adjacentto ester)

d^

2.29–2.37(CH

2

adjacentto ester)

d^

2.23 (CH

2

adjacent toester)

d^

C

A

O (amide)

1.58 (CH

2

prominentpeakattachedto amide)

d^

1.58(CH

2

attachedto amide)

d^

1.58 (CH

2

attached toamidegroup)

d^

1.58 (CH

2

attachedto amide)

C

A

C

d^

2.0 (CH

2

attachedto C

A

C)

(CH

2

attachedto C

A

C)

d^

2.0 (CH

2

attached toC

A

C)

pronounced

d^

2.02 (CH

2

attachedto C

A

C)

C

O

N

d^

d^

3.43 (broadandsuppressedpeak)

C

O

O

O

C

1305 and 1280

Benzene ring

d^

d^

d^

(attributed tobenzene ring702, 750)

d^

Aliphatic chain

d^

d^

d^

d^

Terminal

methyl

d^

d^

d^

d^

Methyl group

of TDI

d^

d^

2.2–2.26(closelyspacedpeaks)

1864 AHMAD ET AL.

to the above limit. The physicomechanical

and chemical characteristics of APEAU

coatings are much better than those of

PEAU or APEA coatings. The specular

gloss of APEAU coatings is the highest

among the resin studies.

This work was funded by ARDB (Ministry of Defense, India) through Grant No. Aero/RD-134/110/106/934.

REFERENCES

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  10. Saunders, K. J. Organic Polymer Chemistry, 2nd ed.; Chapman & Hall: New York, 1981; pp. 366,
  12. Nylen, P.; Sunderland, E. Modern Surface Coat- ings; Wiley: London, 1965; p. 218.

Table V Performance of Polyesteramide Urethane and Alumina-Filled Polyesteramide Urethane at Different Temperatures

Temperature (°C)

PEAU

(Gloss at 60°)

APEAU

(Gloss at 60°)

50 130 160 75 130 160 100 130 160 125 130 160 150 100 (turns brownish)

200 70 110 (turns brownish) 225 65 110 250 Turns black 103 275 — 97 300 — Turns black

POLYESTERAMIDE ANTICORROSIVE COATINGS 1865