Yellow mixtures form on adding essentially colorless N,N-dimethyl-p-toluidine (DMPT) to colorless methacrylate monomers containing phthalate, isophthalate, or terephthalate diester groups. The color-causing interactions between the amines and monomers were investigated using ultraviolet spectroscopy. Equations were derived for predicting interactions between formulation ingredients and DMPT that would lead to undesired color.
Barton, J.A. , JR.; Burns, C.L.; Chandler , H.H.; and Bowen, R.L.: An Experimental Radiopaque Composite Material , J Dent Res52: 731-739, 1973.
3.
Chandler, H.H. ; Bowen, R.L.; Paffenbar-Ger , G.C.; and Mullineaux, A.L.: Clinical Evaluation of a Radiopaque Composite Restorative Material after Three and a Half Years, J Dent Res52: 1128-1137, 1973 .
4.
Argentar, H. , and Bowen, R.L.: Unpublished results.
5.
Bowen, R.L., and Argentar, H.: Tertiary Aromatic Amine Accelerators with Molecular Weights Above 400, J Dent Res51: 473-482, 1972.
6.
Bowen, R.L., and Argentar, H.: Tertiary Aromatic Amine Accelerators in Dental Compositions, US Patent No. 3,740,850, June 26, 1973.
7.
Kosower, E.M.: Reactions Through Charge-Transfer Complexes, in Cohen, S.G.; Streit-Wieser, A., Jr.; and Taft, R.S. (eds) : Progress in Physical Organic Chemistry, Vol 3, New York: Interscience Publishers, 1965.
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Levanon, H., and Navon, G.: The Spectrum and Stability of Oxygen Iodide Charge-Transfer Complex , J Phys Chem73: 1861-1868, 1969 .
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Labudde, R.A. , and Tamres, M.: Linear Regression Models in the Study of Charge-Transfer Complexation, J Phys Chem74: 4009-4014, 1970.
12.
Lutskii, A.E. , and Gol'berkova , A.S.: The Absorption Spectra of Disubstituted Benzenes with Similarly Directing Functional Groups. VI. Phthalic Acids and Their Methyl Esters, J Gen Chem (USSR) 33: 1591-1596, 1963 .
13.
Kloffper, W. , and Willicks, W.: Spektroskopische Untersuchungen an polymeren Donator-Acceptor-Komplexen und Synthese von polymeren Elektronendonatoren , Makromol Chem115: 156-177, 1968.
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16.
Reichardt, C.: Empirical Parameters of the Polarity of Solvents , Angew Chem (Eng)4: 29-40, 1965.
17.
Carrión, J.P.; Donzel, B.; Deranleau, D.; Esko, K.; Moser, P.; and Schwyzer, R.: Inter- and Intramolecular Charge Transfer Complexes in Polypeptides , in Beyerman, H.C.; Van Delinoe, A.; and Van Denbrink, W.M. (eds) : Peptides, Amsterdam , The Netherlands: North-Holland Publishing Co., 1967.
18.
Carrión, J.P. ; Deranleau, D.A.; Donzel , B.; Esko, K.,; Moser, P.; and Schwyzer, R.: Elektronen-Donator-Acceptor-Komplexe bei Polypeptiden II. Problemstellung und orientierunde Versuche mit Acceptoren des neuen Phthalimid Typs, Helv Chim Acta51 :459-481, 1968.
19.
Finar, I.L.: Organic Chemistry, The Fundamental Principles, 4th ed, Vol 1, New York: John Wiley & Sons, Inc., 1963, p 771.
20.
McDaniel, D.H. , and Brown, H.C.: An Extended Table of Hammett Substituent Constants Based on the Ionization of Substituted Benzoic Acids , J Org Chem23: 420-427, 1958.
21.
Herzberg, G.:. Atomic Spectra and Atomic Structure, New York: Dover Publications, 1944, pp 8-9.
22.
Anonymous: ASTM Metric Practice Guide, National Bureau of Standards Handbook 102, Washington, DC: US Government Printing Office, 1967.
Schaefer, J.P. , and Miraglia, T.J.: Ionization Constants of 3,5-Dimethyl 4-Substituted Benzoic Acids, J Am Chem Soc86: 64-67, 1964.
25.
Leffler, J.E. , and Grunwald, E.: Rates and Equilibria of Organic Reactions , New York: John Wiley & Sons, Inc., 1963.
26.
Wells, P.R. : Linear Free Energy Relationships, Chemical Reviews63: 171-219, 1963.
27.
Kravtsov, D.N. , and Faingor, B.A.: Charge-Transfer Complexes of Mercurated Dimethylanilines with Trinitrobenzene, Izv Akad Nauk SSSR, Ser Khim1968 (2) : 289-296 Chem Abst 69: 66717v, 1968.
28.
Barlatier, A.; Meyer, R.; and Vincent, E.J.: Interactions Moleculaires Entre L'-Hexafluorobenzene et Differentes Bases Aromatiques, C R Acad Sci (Paris) C:273, 789-792, 1971.
29.
Beaumont, T.G. , and Davis, K.M.C.: Multiple Charge Transfer Bands in Complexes of Hexafluorobenzene with Aromatic Amines, Nature218: 865, 1968.
30.
Charton, M. : The Estimation of Hammett Substituent Constants , J Org Chem28: 3121-3124, 1963 .
31.
Chowdhury, M.: Absorption Maxima of Some Molecular Complexes , J Phys Chem66: 353-354, 1962.
32.
Computer program LMREG written in BASIC language supplied by Honeywell, Inc. was used.
33.
Afifi, A.A., and Azen, S.P.: Statistical Analysis : A Computer Oriented Approach, New York: Academic Press, Inc., 1972 , pp 107-117.
34.
Ku, H.H. : Notes on the Use of Propagation of Error Formulas , J Res NBS (Engineering and Instrumentation)70C: 263-273, 1966.
35.
Antonucci, J.M. , and Argentar, H.: Unpublished results.
36.
Phillips, R.W. : Skinner's Science of Dental Materials, 7th ed, Philadelphia: W. B. Saunders Co., 1973, pp 219-220, 232-233.
37.
O'Driscoll, K.F.; Konen, T.P.; and Connolly , K.M.: Kinetics of Polymerization of Styrene Initiated by Substituted Benzoyl Peroxides. IV. Decomposition Induced by Substituted Diethylanilines, J Poly Sci (A-1) 5: 1789-1795, 1967 .
38.
Ayrey, G.: Uses of Isotopes in Addition Polymerization, Chem Rev63: 645-667, 1963.
39.
Bowen, R.L., and Antonucci, J.M.: Dimethacrylate Monomers of Aromatic Diethers, J Dent Res54: 599-604, 1975.
40.
Antonucci, J.M. , and Bowen, R.L.: Dimethacrylate Monomers of Aromatic Ether-Esters , J Dent Res54 (Special Issue A) : Abstract No. L441, 1975.
