A compound (BHM) was synthesized that can stabilize monomers by inhibiting premature polymerization but that can serve as a monomer in the polymerization after the initiator system is activated. The structural formula of BHM (3,5-di-tert-butyl-4-hydroxybenzyl methacrylate) was confirmed by nuclear magnetic resonance analysis.
Get full access to this article
View all access options for this article.
References
1.
Knock, F.E., and Glenn, J.F.: Dental Material and Method, US Patent No. 2,558,139, June 26, 1951.
2.
Bowen, R.L.: Dental Filling Material Comprising Vinyl Silane Treated Fused Silica and a Binder Consisting of the Reaction of Bisphenol and Glycidyl Acrylate , US Patent No. 3,066,112, Nov 27, 1962.
3.
Bowen, R.L., and Argentar, H.: Diminishing Discoloration in Methacrylate Accelerator Systems, JADA75:918-923, 1967.
4.
Morris, R.C.; Rocklin, A.L.; and Sax, K.J.: Hydroxybenzyl Esters, US Patent No. 3,116,305, 1963 .
5.
Kleiner, E.K.: Procêdé de Preparation d'Anti-oxydants Polymères à Groupes Phénoliques Empêchés , French Patent No. 2,001,412, 1970.
6.
Coppinger, G.M. , and Campbell, T.W.: Reaction Between 2,6-Di-t-butyl-p-cresol and Bromine, J Am Chem Soc75:734-736, 1953.
7.
Bhacca, N.S.; Johnson, L.F. ; and Shoolery, J.N. (eds): NMR Spectra Catalog, Palo Alto, Calif: Varian Associates, 1962.
8.
Bible, R.H. : Interpretation of NMR Spectra, An Empirical Approach, New York: Plenum Press , 1965, pp 9-14.
9.
Jackman, L.M. , and Sternhell, S.: Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, 2nd ed, New York: Pergamon Press , 1969, pp 11-13, 48-49.
10.
Rummens, F.H.A. : The Chemical Shift: A Review, Organic Magnetic Resonance2:209-217, 1970.
11.
Bible, R.H. : Interpretation of NMR Spectra, An Empirical Approach, New York: Plenum Press , 1965, p 26.
12.
Natrella, M.G. : Experimental Statistics, NBS Handbook 91 , Washington, DC: US Government Printing Office, 1963, chap 6, pp 7-21 and list of errata.
13.
Mandel, J.: The Statistical Analysis of Experimental Data, New York : Interscience Publishers, 1967, pp 132-141.
14.
Jackman, L.M. , and Sternhall, S.: Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, 2nd ed, New York: Pergamon Press , 1969, pp 10, 11, 13.
15.
Eisenhart, C.: Realistic Evaluation of the Precision and Accuracy of Instrument Calibration Systems, J Res NBS67C:161-187, 1963.
16.
Tobin, W.W. : Antioxidants, in Modern Plastics Encyclopedia, New York: McGraw-Hill, Inc., 1970 -1971, pp 314-321.