This Article Abstract Full Text (PDF) Alert me when this article is cited Alert me if a correction is posted Citation Map Services Email this article to a friend Similar articles in this journal Similar articles in PubMed Alert me to new issues of the journal Add to Saved Citations Download to citation manager Request Permissions Request Reprints Add to My Marked Citations Citing Articles Citing Articles via HighWire Citing Articles via Google Scholar Citing Articles via Scopus Google Scholar Articles by Stansbury, J.W. Articles by Liu, D.-W. Search for Related Content PubMed PubMed Citation Articles by Stansbury, J.W. Articles by Liu, D.-W. Social Bookmarking                         What's this?

Preparation and Characterization of Cyclopolymerizable Resin Formulations

Dental and Medical Materials Group, Polymers Division, Bldg. 224/Rm. A-143, National Institute of Standards and Technology, Gaithersburg, Maryland 20899

B. Dickens

Dental and Medical Materials Group, Polymers Division, Bldg. 224/Rm. A-143, National Institute of Standards and Technology, Gaithersburg, Maryland 20899

D.-W. Liu

Dental and Medical Materials Group, Polymers Division, Bldg. 224/Rm. A-143, National Institute of Standards and Technology, Gaithersburg, Maryland 20899

An amine-catalyzed reaction between acrylates and formaldehyde has been used to convert mono-acrylates to difunctional monomers and di-acrylates to multifunctional oligomers by linking the acrylic double bonds together in 1,6-diene pairs. The resulting monomers and oligomers undergo efficient cyclopolymerization to high conversion with significantly less shrinkage than normally found for acrylates. In this study, a convenient single-step process was used with mixtures of mono- and di-acrylate starting materials to produce a series of resins with potential for effective cyclopolymerization. Incremental changes in the ethyl acrylate (EA) to ethoxylated bisphenol A diacrylate (EBPAD) ratio directly supplied cyclopolymerizable resins with a broad range of viscosities and product distributions. Those resins produced from reaction mixtures rich in EA have low viscosities because of high diluent monomer contents and limited oligomerization of EBPAD due to end-cap formation. Resin viscosity and average molecular weight of the oligomeric component of the resin were inversely related to the amount of EA used in the reaction. Through the choice of reactants and their ratio, this simple technique has the potential to provide cyclopolymerizable resins for use in a variety of dental polymer applications.

Key Words: cyclopolymerizable resins

REFERENCES

• Butler GB (1986). Cyclopolymerization. In: Encyclopedia of polymer science and engineering. Vol. 4. New York, NY: John Wiley and Sons, Inc., pp. 543-598.
• Butler GB, editor (1992). Cyclopolymerization and cyclocopolymerization. New York: Dekker.
• Colletti RF, Halley RJ, Mathias LJ (1991). Mechanism study of the base-catalyzed ether formation involving a-(hydroxymethyl)acrylates. Macromolecules 24:2043-2047. Feilzer AJ, DeGee AJ, Davidson CL (1987). Setting stress in composite resin in relation to configuration of the restoration. J Dent Res 66:1636-1639.
• Jensen ME, Chan DCN (1985). Polymerization shrinkage and microleakage. In: Posterior composite resin dental restorative materials. Vanherle G, Smith DC, editors. The Netherlands: Peter Szulc Publishing Co., pp. 243-262. Mathias LJ, Dickerson CW (1991). Acrylate-containing oligo(ether-ester) cross-linking agents with controlled molecular weight via end-group termination. Macromolecules 24:2048-2053.
• Mathias LJ, Kusefoglu SH (1987). New difunctional methacrylate ethers and acetals: Readily available derivatives of a-hydroxymethyl acrylates. Macromolecules 20:2039-2041.
• Mathias LJ, Kusefoglu SH (1988). Cyclopolymerization of the ether of methyl a-(hydroxymethyl)acrylate. Macromolecules 21:545-546.
• Stansbury JW (1990). Cyclopolymerizable monomers for use in dental resin composites. J Dent Res 69:844-848.
• Stansbury JW (1991). Difunctional and multifunctional monomers capable of cyclopolymerization. Macromolecules 25:2029-2035.
• Stansbury JW (1992). Synthesis and evaluation of novel multifunctional oligomers for dentistry. J Dent Res 71:434-437. Stansbury JW (1993). Observations related to the amine-catalyzed coupling reaction of aldehydes and acrylates. Macromolecules 26:2981-2982.
• Suliman AA, Boyer DB, Lakes RS (1993). Interferometric measurements of cusp deformation of teeth restored with composites. J Dent Res 72:1532-1536.
• Tsuda T., Mathias LJ (1993). Cyclopolymerization of a-(hydroxymethyl)acrylic acid ether dimer: Dependence of cyclopolymerizability on polymerization conditions. Polym Prep (Am Chem Soc, Div Polym Chem) 34(2):346-347.
• Wei SHY, Barkmeier WW (1992). Conference report: International symposium on adhesives in dentistry. J Dent Res 71:75-77.

Journal of Dental Research, Vol. 74, No. 4, 1110-1115 (1995)
DOI: 10.1177/00220345950740041201


CiteULike    Complore    Connotea    Del.icio.us    Digg    Reddit    Technorati    Twitter    What's this?

This article has been cited by other articles:

				R.R. Braga and J.L. Ferracane ALTERNATIVES IN POLYMERIZATION CONTRACTION STRESS MANAGEMENT Critical Reviews in Oral Biology & Medicine, May 1, 2004; 15(3): 176 - 184. [Abstract] [Full Text] [PDF]

This Article Abstract Full Text (PDF) Alert me when this article is cited Alert me if a correction is posted Citation Map Services Email this article to a friend Similar articles in this journal Similar articles in PubMed Alert me to new issues of the journal Add to Saved Citations Download to citation manager Request Permissions Request Reprints Add to My Marked Citations Citing Articles Citing Articles via HighWire Citing Articles via Google Scholar Citing Articles via Scopus Google Scholar Articles by Stansbury, J.W. Articles by Liu, D.-W. Search for Related Content PubMed PubMed Citation Articles by Stansbury, J.W. Articles by Liu, D.-W. Social Bookmarking                         What's this?