Synthesis, Characterization and Curing Studies of Thermosetting Epoxy Resin with Amines

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1 7 Bull. Koran Chm. So., Vol., o. 8 Lakshmi. B t al. DI /bks Synthsis, Charatrization an Curing Stuis of Thrmostting Epoxy Rsin with Amins Lakshmi. B, Shivanana. K.,,* an Mahnra. K. * Dpartmnt of Stuis in Chmistry, Cntral Collg Campus, Bangalor Univrsity, Bangalor-56 Shulih Faulty of Chmistry, Thnion - Isral Institut of Thnology, Thnion City, Haifa -, Isral * shivanana_kn@yahoo.om Riv tobr, 9, Apt Jun, A nw hybri thrmostting malimio poxy ompoun -(-malimiophnyl) glyiylthr (-MPGE) is prpar by rating -(-hyroxyphnyl) malimi (HPM) with Epihlorohyrin by using bnzyltrimthylammonium hlori as a atalyst. Th rsulting ompoun posssss both th oxiran ring an malimi group. Th uring ration of ths malimiophnyl glyiylthr poxy ompoun (-MPGE) with amins as uring agnts suh as thylniamin (EDA), ithylntriamin (DETA) an trithylnttramin (TETA), aminothylpiprazin (AEP) an isophoroniamin, IPDA), ar stui. Inorporation of malimi groups in th pihlorohyrin provis yli imi strutur an high ross-linking nsity to th ur rsins. Th ur sampls xhibit goo thrmal stability, xllnt hmial (ai/alkali/solvnt) an watr absorption rsistan. Morphologial stuis by th SEM thniqu furthr onfirm th phas homognity nt work of th ur systms. Ky Wors: Amin, Epoxy rsin, Malmi, Curing, Epihlorohyrin Introution Epoxy rsins ar wily us in inustrial appliations owing to thir many attrativ proprtis, suh as xllnt hmial an solvnt rsistan, goo thrmal an ltrial proprtis. thr major appliations of poxy rsins inlu th manufatur of print iruit boars, omposits, tooling an asting, ahsivs an puttis. Civil nginring uss of poxy rsins inlu flooring, rak injtion, grouts, salants, paving an onrt flooring. Epoxis an b mploy in two-pak, ambint ur maintnan oatings. In many appliations amins, anhyris, fatty ais, arylis, polystrs, polyisoyanis an amis ar us as uring agnts to stuy th fft on th uring rat an rlat proprtis. At prsnt poxy rsins ar xtnsivly us in thnial appliations suh as oatings, omposits an as strutural ahsivs. Us of poxy rsins in high prforman strutural matrial is gtting mor an mor popular. Thr is a lot of sop an n for improving th proprtis of poxy rsins to b us in avan appliations. For xampl, poxy rsin with suprior thrmal stability is n for using as moling ompouns an napsulation matrials in avan ltroni omponnts. Gnrally, moifying poxy rsin with polyamis or imio ompouns - provis a onvnint approah of nhaning th thrmal stability of poxy rsins. Thrfor, poxy rsins wr ur with rativ polyimis, - polyami ai, 5 an imiomoifi uring agnts 6 to introu imi strutur into poxy rsin. Th thrmal stability of th abov mntion imio poxy rsins was signifiantly lvl up both in th initial omposition (IDT) an th intgral proural omposition (IPDT). 7 n th othr han, poxy rsins moifi with malimi ompouns also riv attrativ attntions, u to th similar uring onitions an prossing proprtis of th poxy rsins an malimis. Malimi-poxy rsins usually show appropriat proprtis btwn poxy an malimi rsins. Thus, both th intrross an th intrpntrating systms (IP) bas on bismalimis an poxy rsins wr prpar whih xhibit goo thrmal an mhanial proprtis Aitionally, sin imi groups oul provi har formation in th onns phas to improv polymrs flam rtarant proprtis, poxy rsins moifi with imi ompouns through hmial rations or physial blning hav bn rport to show goo flam rtarant proprtis. 8- In this papr w first synthsiz a malimi ompoun with a hyroxyl group. W obtain malimiophnyl glyiylthr poxy ompouns through a simpl aition ration btwn th oxiran group of pihlorohyrin an hyroxyl group of th malimi. Th rsulting malimiophnyl glyiylthr poxy ompoun possss (posssss) both oxiran ring an malimi rativ groups. Eah of th rativ groups might form ross-mlinking ntworks unr thrmal uring ration with uring agnts to bring about high ross-linking nsity. So it is onsir worthwhil to stuy th synthsis, haratrization an uring ration of th malimiophnyl glyiylthr poxy ompouns with iffrnt amins an to stuy proprtis of th ur rsin systms. Th ur sampls ar foun to hav goo thrmal stability, hmial rsistan an watr absorption rsistan. Th ur sampls xhibit homognity with no phas sparation whih was onfirm by sanning ltron mirosopy (SEM). Exprimntal Stion Matrials. Mali anhyri an -aminophnol wr purhas from S..Fin hmials. Th following amins wr us. Ethylniain (EDA), ithylntriamin (DETA), trithylnttramin (TETA), -(-aminothyl) piprazin (AEP)

2 Curing Stuis of Epoxy Rsin with Amins Bull. Koran Chm. So., Vol., o. 8 7 an 5-amino-,,-trimthylylohxanmthylamin (isophoroniamin, IPDA), an bnzyltrimthyl ammonium hlori (BTAC) wr suppli by Alrih Chmials. Dimthylformami (DMF), p-tolunsulphoni ai, tolun, soium biarbonat, thyl atat, H S, H,, C 6H 6, CH H, H an ah wr obtain from Mrk Chmials. Infrar sptra wr ror using iolt FT-IR sptromtr using KBr. Elmntal analyss wr arri out in Liqui Crystal Dpartmnt, Raman Rsarh Institut, Bangalor. Th H MR sptra of MIE ompoun is ror in Sophistiat Instrumnt Faility, Inian Institut of Sin, Bangalor. TGA an DSC for ur sampls is ror in ational Chmial Laboratory, Pun. Synthsis of -(-hyroxyphnyl) malimi (HPM). Exprimntal prour for th synthsis an haratrization of HPM is th sam as givn in prvious works, by th authors. Synthsis of -(-malimiophnyl) glyiylthr (-MP- GE). HPM (. mol, 8.7 g) was mix with g of pihlorohyrin (ECH) in a 5 ml -nk flask quipp with a stirrr, onnsr, an a nitrogn inlt. Aftr aing BTAC (.8 g,. mol) to th solution, th mixtur was stirr unr nitrogn for h at 6 o C. Exss ECH was rmov unr ru prssur an th soli rsiu was issolv in thyl atat, wash with watr an ri ovr MgS. Th prout was purifi by hromatography using a silia olumn an thyl atat/ tolun (: in vol.) to giv MPGE prout (yil 55%; mlting point, 5-5 o C; poxy quivalnt wight = 5). IR (KBr, m ) 75 (C= bning), 9 (oxiran-ring), 8, 7 (Ph- -), 75 (C- strthing), 69 (C=C), 75 (C= symmtri strthing), 78 (C= asymmtri strthing), 7 (C- H of imi group). H MR ( MHz, DMS- 6, ppm).7 an.87 (H, -() );.68 ( H,- CH()-);.-.6 (H, -Ph--); 6.87 (H, -CH=CH-); (H, aromati protons). Prparation of ur poxy rsins. Th ur poxy rsins wr obtain by thrmally uring of poxy rsin (-MPGE) with amins suh as thylniamin (EDA), ithylntriamin (DETA)trithylnttramin (TETA),-(-aminothyl) piprazin (AEP) an 5-amino-,,-trimthyl ylohxanmthylamin (isophoroniamin, IPDA) as uring agnts. Epoxy rsin (-MPGE) an th amins wr issolv in mthylthylkton to form a homognous solution. Aftr vaporating th solvnt at ambint th mixtur was ur with spifi uring onition to rsult in ur rsins. Th uring onitions ar list in Tabl. Moistur absorption an hmial rsistan masurmnts. Watr absorption an hmial rsistan tsts ar onut as xplain in th prvious works by th authors., Th hmial rsistan tsts wr arri out in aton H S, H,, C 6H 6, CH H, H an ah solutions. W us sam thiknss sampls for th tsts. An avrag of thr sampl raings is ror at room. Rsults an Disussions Prparation of -MPGE poxy ompoun. -(-Malimiophnyl) glyiylthr (-MPGE) was prpar from rating pihlorohyrin with -(-hyroxyphnyl)malimi (HPM) whih was synthsiz. aoring to Shm. Th first attmpt of synthsizing -MPGE was prform unr basi onitions by mploying KH as a atalyst. Th ru prout was analyz with thin layr hromatography whih show ompliat ompositions ontaining various by prouts. Th pur -MP- GE was obtain by mans of olumn hromatography with a low yil of lss than 5%. Th strong basi onition of th ration might aus th hyrolysis of th imi groups of HPM an -MPGE, thrfor, to rsult in mix by prouts. To ompnsat for this flaw, bnzyltrimthyl ammonium hlo- Tabl. Prparation an uring onitions an thrmal stability of ur systms valution with TGA an DSC unr air atmosphr Sl. o Systm Curing onitions Thrmal stability DSC ata IDT o C IPDT o C T o no C T o xo C -MPGE EDA 5 o C ( h), 7 o C ( h) MPGE DETA 5 o C ( h), 7 o C ( h) MPGE TETA 5 o C ( h), 7 o C ( h) MPGE AEP 5 o C ( h),7 o C ( h) MPGE IPDA 5 o C ( h), 7 o C ( h) H H Aton rt h H H H p-tsa, DMF / tolun o C H HPMA HPM HPM Cl-CH- KH, EtH, rt 8 h CH-CH-CH- Shm. Prparation of -malimiophnyl glyiyl thr of poxy ompoun

3 7 Bull. Koran Chm. So., Vol., o. 8 Lakshmi. B t al. % T C=C C C= 5 Phnyl m oxiran ring Ph Ph-- Figur. FT-IR sptrum of -(-malimiophnylglyiylthr) ppm Figur. H MR sptrum of MPGE. Exothrm ( o C) 8 6 -CH-CH-CH b a Rativity Stuis of -MPGE with amins b a EDA EDA DETA TETA AEP AEP IPDA 6 8 Tim in min Figur. Rativity stuis of -malimiophnylglyiyl thr of rsin with amins at room. Tabl. Rativity stuis ata of -malimiophnylglyiyl thr of poxy ompoun with amins Sl. o Systm Wight of -MPGE (g) Wight of amin (g) Curing Tim in min Exothrm ( o C) -MPGE EDA.5 5 ± 9 ±. -MPGE DETA.6 5 ± 5 ±. -MPGE TETA.76 8 ± 58 ±. -MPGE AEP. 5 ± ±.6 5 -MPGE IPDA.5 65 ± ±. ri (BTAC), whih was rport bing usful in th synthsis of glyiyl phosphinat ompouns without ausing hyrolysis of th phosphinat ompouns, -7 was utiliz in th synthsis of -MPGE. Th prout yil was signifiantly rais by about 75%. Th hmial strutur of -MPGE ompoun was assign on th basis of FT-IR, lmntal analysis an H MR stuis. Th absorption pak at aroun 95 m whih was obsrv in th FT-IR sptrum of -MPGE (Figur ) monstrats th formation of oxiran groups. Th absorption paks riving from th yli malimi group wr also obsrv at 78 (C= asymmtri strthing), 78 (C= symmtri strthing), an 75 (C- strthing), an 6 (C=C) m. thr spifi absorption bans at 7 (C=C-H), 5, 7 (Ph--), an 5 m (phnyl) gav mor vin to th obtain ompoun having th xpt hmial strutur. Furthr haratrization was prform with H MR analysis on th MIE ompoun whih also iniat th propos hmial strutur as shown in th Shm (Figur ). Th H MR signals obsrv ar assign as blow;.888 ppm an.678 ppm (H, -() );.8 ppm (H, -CH()-); 75 ppm (H,-Ph- -); 6.87 ppm (H,-CH=CH-); an ppm (H, aromati protons). Th hmial shifts of th absorption paks an th ara ratios of th pak intgration wr foun to b onsistnt with th xpt hmial strutur. Morovr, th xprimntal rsults of titration of poxy quivalnt wight also monstrat th sussful of synthsis of -MPGE ompoun. -MPGE is solubl in most of th inustrially solvnts, suh as aton, mthylthylkton, ttrahyrofuran,,-imthylatami, imthylsulfoxi, thyl atat, mthanol, thanol, -mthyl--pyrrolion an imthylformami. Th goo organo-solubility of -MPGE suggsts its goo prossibility assoiat with th urrnt inustrial prosss. Curing rations of -MPGE with amins. Th uring ration btwn -MPGE with amins is arri out with iffrnt amins suh as EDA, DETA, TETA, AEP an IPDA bas on thir hyrogn quivalnt wights. -MPGE rsin was takn on an aluminum foil of about m iamtr an th amin was a an mix thoroughly for a minut using a thin woon stik. In all th ass, th of th ration mixtur at iffrnt intrvals of tim was masur using an infrar gun an th ompltion of th uring pross is iniat whn th ration mixtur bam non-stiky to th woon stik. Th avrag of th thr riings is list in Tabl. Th poxi groups in th rsin rat with th amin to form a highly ross link, thr imnsional ntwork. Th uring pross onvrts th poxy rsin into a har, infusibl an rigi matrial. All th uring rations wr arri out at room (6 o C). Th mhanism of uring ration is givn in Shm. Th rativity ata (s Tabl an Figur ) larly iniats that th rativity trn inrass in th orr AEP > TETA > DETA > EDA > IPDA. Th rativity mainly pns on th natur of amino groups prsnt in th uring agnts. Ethylniamin has only primary amin group whras ithyln-

4 Curing Stuis of Epoxy Rsin with Amins Bull. Koran Chm. So., Vol., o H - H : : -CH- --C 6 H -- -H- -CH- --C 6 H : : -- -CH- --C 6 -CH- --C 6 H H - CH -CH-CH --C H 6 -CH- -C 6 H --H - -CH- --C 6 - -CH- -C 6 --H : : -CH- --C 6 Shm. Th ration mhanism of amin with oxiran ring H -CH- --C 6 - -CH- --C 6 -CH- --C 6 -CH- --C 6 H.. : -H C-CH- -. : --- -H C-CH- _ -H C-CH-. : - _.. : --- -H C-CH- Shm. Slf-aition ration of malimi groups of -MPGE ompoun triamin an trithylnttramin hav both primary an sonary amin groups. In th as of aminothylpiprazin, th inras in rativity may b xplain u to th umulativ ffts of primary, sonary an trtiary amino groups prsnt. Th slow rativity in th as of isophoroniamin may b baus of its aliyli haratr vn though it has a primary amino group. Th rsin is ross link by rativ moluls whih link aross th poxy units an bom part of th strutur. Ths ata larly iniat that th ur -MPGE with th uring agnts (EDA, DETA, TETA, AEP, an IPDA) show that th AEP is mor rativ whn ompar to th othr Hat Flow...5 b a Tmpratur ( o C) Figur. Dynami DSC thrmograms of th fiv systms a) -MPGE EDA, b) -MPGE DETA, ) -MPGE TETA. ) -MPGE AEP an ) -MPGE IPDA. amins. This an b possibly rit to th prsn of trtiary nitrogn atom in AEP (ats as atalyst), whih alrats th uring rat to a vry high valu as ompar to othr amins amins. - It is also wll known that both th oxiran group an malimi group rat with amin groups through slf aition rations (Shm ). Morovr, th malimi groups might rosslink through slf-aition ration unr hating. 9 Thrfor, whil uring -MPGE with uring agnts, all th thr abovmntion rations might our. In this work, th uring ompositions wr takn with th sam stoihiomtri amounts of th amin uring agnt an oxiran groups. Thrfor, most of th amin groups ar xpt to rat with oxiran groups at low rgion. Sin almost no amino group was lft

76 Bull. Koran Chm. So., Vol., o. 8 Lakshmi. B t al. Driv. Wight (% min) b a 5.5.5.5 H ah H EtH HS H 5 6 Tmpratur ( o C) Figur 5.

.5 H ah H EtH (a) -MPGE EDA (b) -MPGE DETA.5.5 HS H () -MPGE TETA () -MPGE AEP 5 5 5 5 Figur 8. Chmial/moistur absorption rsistan of -MPGE with DETA at room. () -MPGE IPDA Figur 6.

to rat with malimi group, only slf-aition ration ourr for malimio groups in th uring ration. Th rsulting prouts obtain wr thrfor suppos to hav high ross linking nsitis.

Th ynami sans wr prform at a hating rat of o C/min an th ata ar summariz in Tabl. From th figur it is lar that all th ur systms xhibit similar bhaviour.

Th pak at aroun to 5 o C is attribut to th xothrmi uring rations of th abov mntion poxy an amins systms an th maximum of th xothrmi pak obtain at - 6 o C.

5 76 Bull. Koran Chm. So., Vol., o. 8 Lakshmi. B t al. Driv. Wight (% min) b a H ah H EtH HS H 5 6 Tmpratur ( o C) Figur 5. Thrmogravimtri analysis (TGA) a) -MPGE EDA, b) -MPGE DETA, ) -MPGE TETA. ) -MPGE AEP an ) -MPGE IPDA Figur 7. Chmial/moistur absorption rsistan of -MPGE with EDA at room..5 H ah H EtH (a) -MPGE EDA (b) -MPGE DETA.5.5 HS H () -MPGE TETA () -MPGE AEP Figur 8. Chmial/moistur absorption rsistan of -MPGE with DETA at room. () -MPGE IPDA Figur 6. Fratur morphology analysis of ur malimiophnyl glyiylthr with iffrnt amins. a) -MPGE EDA, b) -MPGE DETA, ) -MPGE TETA, ) -MPGE AEP an ) -MPGE IPDA. to rat with malimi group, only slf-aition ration ourr for malimio groups in th uring ration. Th rsulting prouts obtain wr thrfor suppos to hav high ross linking nsitis. Diffrntial sanning alorimtri (DSC) stuis of ur systms. Dynami DSC thrmograms of th fiv systms (- MPGE EDA, -MPGE DETA, -MPGE TETA. - MPGE AEP an -MPGE IPDA) ar rprsnt in Figur. Th ynami sans wr prform at a hating rat of o C/min an th ata ar summariz in Tabl. From th figur it is lar that all th ur systms xhibit similar bhaviour. Th pak at 75 to 8 o C orrspons to th mlting point of th ur poxy systms. Th pak at aroun to 5 o C is attribut to th xothrmi uring rations of th abov mntion poxy an amins systms an th maximum of th xothrmi pak obtain at - 6 o C. At about o C, th ompltion of uring pross iniats th absn of xothrm paks in th post ur in poxy amin systms. vr all this iniats all fiv iffrnt -MPGE with amins systms show th similar bhaviors an also whih onforms th homognity of th ur systms. Thrmal proprtis of th ur systms. Th thrmal stability of th malimiophnyl rsin was invstigat with thrmogravimtri analysis (TGA) in air atmosphr (s Figur 5). Th thrmograms of th ur malimiophnyl glyiylthr larly iniat that th thrmal stability of ur rsins was improv with th inorporation of malimi groups into th Epihlorohyrin molul. 6-8 With th inorporation of th

6 Curing Stuis of Epoxy Rsin with Amins Bull. Koran Chm. So., Vol., o H ah H EtH HS H H ah H EtH HS H Figur 9. Chmial/moistur absorption rsistan of -MPGE with TETA at room Figur. Chmial/moistur absorption rsistan of -MPGE with IPDA at room H ah H EtH HS H Figur. Chmial/moistur absorption rsistan of -MPGE with AEP at room. malimi groups, th initial omposition (IDT) of th malimiophnyl glyiylthr poxy rsin was inras (s Tabl ). Th nhanmnt of th thrmal stability u to inorporation of malimi groups on malimiophnyl glyiylthr poxy rsins was thus monstrat. n th othr han, th intgral proural omposition (IPD) also systmatially inras with inorporation of malimi groups. Th high IPDT iniats that th ur malimiophnyl glyiyl poxy ompoun with our hosn amins suh as EDA, DETA, TETA, AEP, an IPDA shows goo thrmal stability. Morphology stuis of ur systms. Th morphology of fratur surfas of ur malimiophnylglyiyl poxy with amins (EDA, DETA, TETA, AEP, an IPDA) wr xamin using sanning ltron mirosop. All th abov mntion fiv systms xhibit similar morphology. From Figur 6 it is larly sn that th fratur surfas of th nat malimiophnylglyiylthr poxy ompoun with amin xhibit a homognous pattrn. All th ur sampls xhibit similar homognous ntwork an show no formation of istint omains, onfirming th formation of a homognous ntwork in all th malimiophnylglyiylthr poxy ur systms. Moistur an hmial rsistan masurmnts of ur systms. Th hmial an watr absorption urvs of th ur -MPGE EDA, -MPGE DETA -MPGE TETA, - MPGE AEP an -MPGE IPDA systms ar shown in Figurs 7-. Th goal of this stuy was to srib th intrations btwn th absorb moistur an poxy ntwork. Th transport of moistur through th poxy ntwork involvs ooprativ motion of watr moluls an -imnsional rsin ntwork. Th quilibrium watr absorption of both systms was almost.7% by wight. n of th major fators affting watr absorption is th prsn or absn of hyrophili groups in th ross-link ntwork. Thr ar sam typs of hyrophili groups in th prsnt systms. Thr ar also othr rlvant fators to onsir, notably fr volums, whih gnrally inrass with ross-link nsity baus of th vlopmnt of a rigi maromolular framwork. As shown in Figurs 7- initially thr is a sharp inras in watr absorption u to watr pntration into strutural fts an avitis on th surfa of sampls. Aftr som tim ( h) a slow pross of watr absorption rahs its quilibrium valu of.7% at room. In th as of hmial rsistan masurmnts th ur systms ar stui with ammonia (as sn in Figurs 7-). Sam trns in wight rution ar obsrv for all th systms. Initially th wight rution is fastr possibly u to washing som of th unrat poxy from surfa of th sampls. Th son stp is a slow wight rution whih an b u to washing som of th unrat poxy out of th bulk of th sampls. Th mor omplx th ntwork is, th longr it taks for ammonia to iffus into th systm to rah to quilibrium. Th wight rution in ammonia rah to its quilibrium valu of about.% aftr h immrsion. Th ai rsistan of th ur systms was tst in th onntrat H S, H,. In ths ass, all th ur systms show similar trn an th almost sam wight rution magnitu. As it is sn in Figurs 7-, thr is almost a total of -.% wight loss whih an probably b rlat to poxy rsins that ar not ontribut in th ntwork formation. This an b u to th

7 78 Bull. Koran Chm. So., Vol., o. 8 Lakshmi. B t al. Tabl. Th maximum moistur/ai/alkali/solvnt rsistan ontnt unr a givn onition of (5 o C) Sl. o Systm % Wight Gain % Wight loss H % ah H C H 5H C 6H 6 H S H -MPGEEDA MPGEDETA MPGETETA MPGEAEP MPGEIPDA fat that in th prsnt stuy w us low onntration of amins as uring agnt was us. Th plots of moistur absorption vs. squar root of tim wr onstrut (Figurs 7-) to not th saturation limits of th absorb moistur. From th figurs it is obsrv that initially th watr uptak inrass, an show a flat profil xhibiting Fikan typ bhavior. Th maximum moistur absorb unr a givn onition of an humiity in as of malimiophnylglyiyl poxy ompoun with th amins show a rasing trn. Th ur sampls wr foun to hav goo hmial rsistan (ai/alkali/solvnt) an watr absorption rsistan as ompar to traitional poxy amin ur systms. 9 This may b baus of th inorporation of malimi groups into th pihlorohyrin, whih provis a yli imi strutur an high ross-linking nsity to th ur rsins. Th maximum moistur/ai/alkali/solvnt rsistan ontnts unr a givn onition of in as of malimiophnyl glyiylthr poxy ompoun with our amins systms ar shown in th Tabl. Ths ata larly iniat that th ur malimiophnyl glyiylthr poxy ompoun with th uring agnts (EDA, DETA, TETA, AEP, an IPDA) show mor rsistan to watr absorption an othr hmials. Th AEP ur systm xhibit slightly high rsistant towars moistur/ai/alkali/solvnt absorption than othr amin ur systms. This may b u to this an possibly b rit to th prsn of trtiary nitrogn 9 (ats as atalyst), whih alrats th uring rat vry muh, rsulting in th high ross-link nsity ntwork whn ompar to othr amins. Conlusions Phnylmalimio group is sussfully inorporat into pihlorohyrin an th rsulting on a ompoun with both oxiran ring an malimio rativ groups. Th ur rsins ar obtain by thrmal uring of th malimiophnyl glyiylthr poxy ompoun with amins (EDA, DETA, TETA, AEP, an IPDA). Amins at as vry goo uring agnts in th as of malimiophnyl glyiyl thr poxy ompoun. Th highr rativity in th as of AEP an b xplain on th basis of trtiary amin group ating as a atalyst along with th primary an sonary amin groups prsnt in it. Th ur sampls xhibit goo thrmal stability an xllnt hmial (ai/alkali/solvnt) an watr absorption rsistan. Morphologial stuis by th SEM thniqu furthr onfirm (onfirm) th phas homognity ntwork of th ur systms. Rfrns. Jons, R. R., Ellis, B., Es.; Chmistry an Thnology of Epoxy Rsins; Lonon, Chapman an Hall: 99; p 56.. Hay, J..; Woofin, B.; Davis, M. High Prporm Polym. 996, 8, 5.. Ishikawa, S.; akatani, M.; Fukua, H.; Yamamoto, S. Jpn Patnt 996, 8, 5.. Agag, T.; Takihi, T. Polymr 999,, Gaw, K.; Kiki, M.; Kakimoto, M.; Imai, Y. Polymr 997, 8,. 6. Kim, W. G.; am, T. Y. J. Polym. Si. Part A: Polym. Chm. 996,, Park, S. J.; Kim, H. C.; L, H. I.; Suh, D. H. Maromoluls,, Kumar, A. A.; Alagar, M.; Rao, RMVGK. Polymr,, Musto, P.; Martuslli, E.; Ragosta, G.; Sarinzi, G. J. Appl. Polm. Si. 998, 69, 9.. Kumar, A. A.; Alagar, M.; Rao, RMVGK. J. Appl. Polym. Si., 8,.. Kumar, A. A.; Alagar, M.; Rao, RMVGK. J. Appl. Polym. Si., 8, 8.. Han, J. L.; Chn, Y. C.; Li, K. Y.; Hsih, K. H. J. Appl. Polym. Si. 998, 7, 59.. Whit, L. A.; Wbr, W. J.; Mathias, L. J. Polym. Bull., 6, 6.. Shibora, T.; kus, S.; Aoki, T.; Kato, H. US Patnt, 6,. 5. Vanaja, A. Ph. D Thsis, Bangalor Univrsity, Bangalor,. 6. Chuan-S, Wu.; Ying-Ling, Liu.; Kh-Ying, Hsu. Polymr,, Ashroft, W. R., Ellis, B., Es.; Chmistry an Thnology of Epoxy Rsin; Lonon, Chapman an Hall: 99; p Liu, Y. L.; Jng, R. J.; Chiu, Y. S. J. Polym. Si. Part A: Polym. Chm., 9, Shivanana, K..; Mahnra, K.. Int. Cong. of Chm. an Envi. 5, 7.. Gun-S, L.; Young-C, L. Myoung-S, G. Bull. Koran Chm. So.,, 9.. Shivanana, K..; Mahnra, K.. Ira. Poly. Jou. 7, 6(), Shivanana, K..; Mahnra, K.. Bull. Koran Chm. So. 6, 7,.. Shivanana, K..; Jagash, R.V.; Mahnra, K.. Journal of Molular Catalysis A Chmial. 6, 55.. Wu, S.; Liu, Y. L.; Chiu, Y. C.; Chiu, Y. S. Polym. Dgra. Stab.,. 5. Wang, C. S.; Shih, J. Y. Polymr 998, 9, Liu, Y, L.; Liu, Y, L.; Chiu, Y. S. J. Polym. Si. Part A: Polym. Chm., 56, Liu, Y. L.; Hsiu, G. H.; Chiu, Y. S.; Jng, R. J. J. Appl. Polym. Si. 996,, 957.

Preparation and Curing Studies of Maleimide Bisphenol A Based Epoxy Resins

1542 Bull. Korean Chem. Soc. 2006, Vol. 27, No. 10 S. K. N. Gowda and K. N. Mahendra Preparation and Curing Studies of Maleimide Bisphenol A Based Epoxy Resins Shivananda Kammasandra Nanjunda Gowda and