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1 Thermal Analysis During Setting of Zinc Oxide-Eugenol Cements H. M. EL-TAHAWI and R. G. CRAIG School of Dentistry, University of Michigan, Ann Arbor, Michigan 4814, USA Characteristic thermal transitions of inc oxide and eugenol materials ere compared ith those of inc eugenolate. It has been accepted traditionally that the setting of inc oxide-eugenol (ZOE) cements is the result of the formation of inc eugenolate crystals.1 A recent study pointed out that at least seven hours elapsed before inc eugenolate crystals precipitated from a clear solution of inc acetate in eugenol.2 Accelerated ZOE, hoever, set in as short a time as three minutes.3 Electron microscopy, electron diffraction,2 and X-ray diffraction4 studies indicated that a set ZOE mix may contain less than 2% inc eugenolate. Even that lo concentration is doubtful because the studies did not identify clearly hether the diffraction patterns ere due to a crystalline or amorphous phase. Differential thermal analysis of set commercial ZOE did not sho the characteristic transition of inc eugenolate on melting.5 These studies suggest that the setting of ZOE cements may not be because of the formation of a inc eugenolate phase. Various studies on the same system indicated that the addition of o-ethoxybenoic acid,6 large amounts of inc acetate dihydrate (accelerator),3 or inc eugenolate poder to standard ZOE mixes improved the mechanical properties of the hardened mass. The purpose of this investigation as to establish the characteristic thermal transitions of ZOE materials, to compare them to those of inc eugenolate, and to study the effect of adding o-ethoxybenoic acid, large amounts of accelerator, and rosin on the formation of inc eugenolate. This investigation as presented at the 48th General Meeting of the TADR, Ne York, NY, March 19, 197. Received for publication April 13, Materials and Methods One commercial* cement dispensed as poder and liquid and several laboratory prepared mixes ere used in this investigation. The materials used to prepare various cement compositions ere as follos: inc oxide (ZnO),t eugenol (E),: inc acetate dehydrate (ZnAc), rosin,ll and o-ethoxybenoic acid (EBA).# Zinc eugenolate as prepared by dissolving inc acetate in eugenol to form a clear solution. After centrifuging, the clear liquid as left to stand and inc eugenolate as precipitated from the solution. The precipitate as ashed from the eugenol several times ith methanol and dried at 45 C. Differential thermal analysis as done at from 25 to 5 C for the various mixes. The analysis as conducted in a nitrogen atmosphere and a heating rate of 25 C/ minute as used. Glass beads ere used as a reference material in all instances, except for inc eugenolate in inc oxide mixtures. Zinc oxide as used as a reference material in these instances. chromelalumel thermocouples ere used. The curves shoed uncorrected temperatures but those reported in the text are corrected values. The relative humidity of the room during mixing as about 25%. Results Thermograms of inc oxide, 1% inc eugenolate, and 8 % inc eugenolate in inc oxide are shon in Figure 1. It can be seen * S.S. White Co., Philadelphia, Pa. Analytical reagent, Mallinckrodt, St. Louis, Mo. t U.S.P., Boler Chem. Co., Detroit, Mich. Reagent grade, J.T. Baker Chem. Co., Phillipsburg, NJ. Supplied by Kerr Mfg. Co., Romulus, Mich. # City Chem. Corp., Ne York, NY. DuPont 9 differential thermal analyer. E.I. Du- Pont de Nemours & Co. (Inc.), Instrument Product Division, Wilmington, Del.

2 Vol 5 No. 2 THERMAL ANALYSIS OF ZOE 431 xo _Zn or Commerical pdr r -j a: a _ oi AT C FIG 2.-Differential temperature (AT) vs concentration of inc eugenolate. used in preparing the laboratory mixes are shon in Figure 3. Eugenol as characteried by one transition, an endotherm indicating boiling at 253 C. Zinc acetate dehydrate shoed endotherms at 15, 111,.5 usp,1 (E) 1 2 e FIG 1. Zinc oxide, inc eugenolate, and 8% inc eugenolate in inc oxide. Ed A Ic/div that ithin the range of temperature used inc oxide had no transitions. Zinc eugenolate as characteried by to endothermic and one exothermic transitions; the endotherms ere at 226 C* and at 251 C, and the exothermic transition as at 348 C. The same transitions ere detected easily at concentrations of 2% inc eugenolate in inc oxide. Belo this concentration only the endotherm characteristic of inc eugenolate melting (251 C) as detectable. The differential temperature (AT) vs the concentration of inc eugenolate in inc oxide is shon in Figure 2. The same sample eight (.5 gm) as used for all the indicated concentrations, and the 251 C endotherm as used to obtain the curve. Differential thermograms of the reactants * All temperature values are corrected temperatures. _ EdJ ic/div Rosin 1 I~~~~ FIG 3. Components used to prepare ZOE and EBA cements.

3 432 EL-TAHAWI AND CRAIG 251, and 355 C. The o-ethoxybenoic acid had an endotherm at 311 C. The thermogram of rosin shoed endotherms at 84 and 393 C. Differential thermograms of unaccelerated mixes of inc oxide and eugenol containing no accelerators ere obtained at various periods of time from the start of mixing. Up to 96 hours the only transition obtained as that characteristic of the boiling of eugenol, and the mix had not set. Thermograms of commercial ZOE mixes during and after setting are shon in Figure 4. During setting the mixture shoed to endothermic transitions characteristic of the boiling points of ater and eugenol. Thermograms of older mixtures indicated a decrease in both endotherms and the simultaneous appearance of to exotherms. A thermogram of a 3-minute-old* mixture shoed no endotherms, but exotherms ere obtained at 353 and 373 C. Thermograms of laboratory prepared ZOE that contained.6% inc acetate are shon in Figure 5. It can be seen that this compound had transitions typical of the commercial product used. The effect of inc acetate concentration on thermograms of ZOE is shon in Figure 6. As the concentration of inc acetate as increased an endotherm starts to appear in I- x FIG 5.-Laboratory Lob Prep 3 Min 23.6 E -.6 Zn Ac 75.8 Zn J Dent Res March-April 1971 Lab Prep 3 Min Tc prepared ZOE mixes E 5c di _ 2.4 Zn Ac 5c/div 74 Zn 1c/div x Commercial 23.6 Liq 76.4 Pdr 3 Mins I io li Tc * Time recorded hen run started. 2c/div. FIG 4.-Commercial ZOE cement. Commercial 23.6 Liq 76.4 Pdr 15 Miss -l TC1 FIG 6.-Effect of inc acetate concentration on thermograms of ZOE laboratory mixes.

4 Vol 5 No. 2 the region of the melting of inc eugenolate. The to exotherms at higher temperatures also ere replaced by one exotherm. When mix containing a 5.6% inc acetate as analyed after 24 hours, an endotherm appeared at the temperature characteristic of the melting of inc eugenolate. The effect of rosin on the reaction beteen inc acetate, inc oxide, and eugenol is shon in Figure 7. The endotherms typical of ZOE mixes ith high accelerator concentration ere flattened. Differential thermograms of mixes containing o-ethoxybenoic acid are shon in Figure 8. A liquid of 62.5% o-ethoxybenoic acid and 37.5% eugenol, by volume, had an endotherm at 285 C, hich as higher than the boiling point of eugenol and loer than that of o-ethoxybenoic acid. Thermograms of the product of the reaction beteen o-ethoxybenoic acid and inc oxide had three endotherms at 9, 35, and 425 C. In addition to these transitions, a thermogram of the reaction product beteen inc oxide, eugenol, and o-ethoxybenoic acid shoed an endotherm at the temperature characteristic of the inc eugenolate melting point; the loer endotherm found for o-ethoxybenoic acid and inc oxide as shifted to 125 C. Discussion Thermograms of inc oxide shoed no transitions ithin the temperature range of interest and therefore could be used as a standard ith mixes of inc oxide and inc FIG 7.-Effect of rosin on the thermograms of ZOE laboratory mixes. rx THERMAL ANALYSIS OF ZOE 433 FIG 8.-ZOE cements containing EBA. eugenolate. The thermograms of inc eugenolate in Figure 1 had to endotherms and one exotherm; the first endotherm as a solid-solid transition and the second at 251 C as the melting transition. The melting point of inc eugenolate is reported as 245 C.' The exotherm for inc eugenolate is interpreted to be a result of decomposition. The sensitivity of the thermal analysis in detecting inc eugenolate as estimated to be.1 % from Figure 2 and using the assumption that a peak one-eighth inch from the base line could be detected at the highest sensitivity. Eugenol had one endothermic transition at 253 C, hich is in agreement ith the boiling point of 255 C. The endotherms characteristic of inc acetate dehydrate ere due to loss of moisture, loss of ater of hydration, melting, and degradation, respectively. The o-ethoxybenoic acid had one endotherm, hich indicated boiling. The to endotherms in the thermograms

5 434 EL-TAHAWI AND CRAIG of rosin ere because of melting and vaporiation. When differential thermograms of a ZOE formulation containing no accelerator ere determined at times of up to 96 hours after the start of mixing, the only transition obtained as that typical of the boiling point of eugenol. This indicates that the reaction beteen inc oxide and eugenol alone produced neither inc eugenolate nor any byproduct that had transitions ithin the temperature range used. Thermograms of the commercial cement used during setting had to endotherms due to the loss of ater and eugenol. These to endotherms disappeared after 15 minutes from the start of mixing and to exotherms ere obtained. The exotherms ere at somehat higher temperatures (5 and 25 C) than the temperature for inc eugenolate decomposition. The thermograms of the set cement ere in general agreement ith those reported by Brauer, Termini, and Bruns5; hoever, the curves reported had large increases in AT at temperatures just above room temperature. This increase as probably a result of setting the heat programmer at too high an initial value ith respect to starting temperature of the sample and is an artifact rather than a real part of the thermogram. A laboratory cement that contained.6% inc acetate had transitions typical of the commercial product. Thermograms of both the commercial and laboratory prepared cements ere obtained at periods of up to to eeks and the curves ere the same. The data presented in Figures 4 and 5 indicate that inc eugenolate crystals do not form during or after setting of conventional ZOE cements; hoever, it does indicate the formation of an amorphous phase characteried by an exothermic transition near the decomposition temperature of inc eugenolate. It should be emphasied that this phase is not characteried by either the solid-solid transition or the melting of crystalline inc eugenolate. Increase in the concentration of inc acetate had to effects on the thermograms of conventional ZOE mixes. The to exotherms of set conventional ZOE ere replaced by one exotherm characteristic of the inc eugenolate, and an endotherm characteristic of the melting of crystalline inc eugenolate as obtained. The endotherm J Dent Res March-April 1971 as more prominent in the thermogram of the mixes 24 hours after setting. These changes suggest the formation of crystalline inc eugenolate in ZOE mixes that contain high concentrations of inc acetate, and may explain the finding that the compressive strength of ZOE as increased as a direct function of inc acetate concentration.2-3 The observations that crystalline inc eugenolate forms as a result of the reaction beteen inc acetate and eugenol in a ZOE mix and does not form as a result of the reaction beteen inc oxide and eugenol of the same clinical consistency, may be based on the different solubility of inc acetate dehydrate and inc oxide in eugenol. The effect of rosin on the endotherms of ZOE mixes ith high concentrations of inc acetate shoed that rosin interfered ith the formation of crystalline inc eugenolate. This may be because of the solution of rosin in eugenol, or the effect of rosin on the precipitation of crystalline inc eugenolate, or both. Differential thermograms of o-ethoxybenoic acid-zoe cements had endotherms characteristic of the melting of crystalline inc eugenolate. Thus the addition of o-ethoxybenoic acid to the system encouraged the formation of crystalline inc eugenolate. The formation of crystalline inc eugenolate in o-ethoxybenoic acid-zoe mixes may be because of the higher solubility of inc oxide in o-ethoxybenoic acid. The solution of a inc salt in a liquid brings inc ions in contact ith eugenol to form inc eugenolate. The observation that crystalline inc eugenolate improves the compressive strength of ZOE2 cements may explain the efficiency of o-ethoxybenoic acid in improving the strength. Conclusions The experimental evidence furnished by this investigation leads to the folloing conclusions: (1) The setting of unaccelerated ZOE mixes, or those accelerated ith concentrations of less than 1 % inc acetate, did not result in the formation of more than trace amounts, if any, of crystalline inc eugenolate. Hence, the setting of these ZOE cements as not due to the formation of such a crystalline phase. (2) Set ZOE mixes had to exotherms in the region of the exotherm for inc eu-

6 Vol 5 No. 2 THERMAL ANALYSIS OF ZOE 435 genolate, hich may indicate the formation of an amorphous inc eugenolate. (3) The presence of large amounts of inc acetate in ZOE mixes caused the formation of an appreciable amount of crystalline inc eugenolate. (4) The addition of o-ethoxybenoic acid to the system resulted in the formation of crystalline inc eugenolate and hence improved the mechanical properties. (5) The addition of rosin to o-ethoxybenoic acid-zoe cements interfered ith the formation of crystalline inc eugenolate. References 1. COPELAND, H.I.; BRAUER, G.M.; SWEENEY, W.T.; and FORZIATI, A.F.: Setting Reaction of Zinc Oxide and Eugenol, J Res Nat Bur Stand 55:133-38, EL-TAHAWI, HTM.: Relationship of Eugenolate Formation to the Setting Mechanism of Zinc Oxide Eugenol Cements, IADR Dental Materials Group Microfilm, Houston, Texas, March MOHAMMED, H.M.: Effect of Some Accelerators on the Setting Time of Zinc Oxide Eugenol Reaction Product, thesis, Northestern University, April NORLING, B.K., and GREENER, E.H.: X-ray Diffraction Studies of the ZnO-Eugenol Reaction, IADR Dental Materials Group Microfilm, San Francisco, California, March BRAUER, G.M.; TERMINI, D.J.; and BRuNs, C.L.: Characteriation of Components of Dental Materials and Components of Tooth Structure by Differential Thermal Analysis, J Dent Res 49:1-11, BRAUER, G.M.; WHITE, E.E.; and MOSHONAS, M.G.: The Reaction of Metal Oxides ith O-ethoxybenoic Acid and Other Chelating Agents, J Dent Res 37:547-56, 1958.

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