| Synthesis of phosphate monomers and bonding to dentin: esterification methods and use of phosphorus pentoxide. | |
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MedLine Citation:
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PMID: 18243472 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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OBJECTIVES: The aim of this study was to synthesize an acidic monomer using an alternative synthetic pathway and to evaluate the influence of the acidic monomer concentration on the microtensile bond strength to dentin. METHODS: The intermediary 5-hydroxypentyl methacrylate (HPMA) was synthesized through methacrylic acid esterification with 1,5-pentanediol, catalyzed by p-toluenesulfonic acid. To displace the reaction balance, the water generated by esterification was removed by three different methods: anhydrous sodium sulfate; molecular sieves or azeotropic distillation. In the next step, a phosphorus pentoxide (4.82 mmol) slurry was formed in cold acetone and 29 mmol of HPMA was slowly added by funnel addition. After the reaction ended, solvent was evaporated and the product was characterized by 1HNMR and FTIR. The phosphate monomer was introduced in a self-etch primer at concentrations of 0, 15, 30, 50, 70 and 100 wt%. Clearfil SE Bond was used as commercial reference. Microtensile bond strength to dentin was evaluated 24h after the bonding procedures, followed by fracture analysis (n=20). Data was submitted to ANOVA and Tukey's post hoc test. RESULTS: The highest yield was obtained (62%) when azeotropic distillation was used, while the reaction with molecular sieves was not feasible. The phosphoric moiety attachment to the monomer was successfully performed with a quantitative yield that reached around 100%. The acidic monomer concentration significantly affected the bond strength and the highest mean (55.1+/-12.8 MPa) was obtained when 50% of acidic monomer was used. CONCLUSION: The synthesis pathways described in the present study appear to be a viable alternative for developing phosphate monomers. |
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Authors:
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Fabrício Aulo Ogliari; Eduardo de Oliveira da Silva; Giana da Silveira Lima; Francine Cardozo Madruga; Sandrina Henn; Márcia Bueno; Marco Antônio Ceschi; Cesar Liberato Petzhold; Evandro Piva |
Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Journal of dentistry Volume: 36 ISSN: 0300-5712 ISO Abbreviation: J Dent Publication Date: 2008 Mar |
Date Detail:
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Created Date: 2008-02-25 Completed Date: 2008-06-02 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 0354422 Medline TA: J Dent Country: England |
Other Details:
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Languages: eng Pagination: 171-7 Citation Subset: D; IM |
Affiliation:
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Operative Dentistry Department, School of Dentistry, Federal University of Pelotas, RS, Brazil. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Acid Etching, Dental
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methods Analysis of Variance Animals Cattle Dental Bonding* Dental Stress Analysis Dentin Dentin Permeability Dentin-Bonding Agents* / chemical synthesis Esterification Magnetic Resonance Spectroscopy Materials Testing Methacrylates / chemical synthesis*, chemistry Molecular Structure Phosphorus Compounds / chemical synthesis, chemistry Resin Cements* / chemical synthesis Spectroscopy, Fourier Transform Infrared Tensile Strength |
| Chemical | |
Reg. No./Substance:
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0/Dentin-Bonding Agents; 0/Methacrylates; 0/Phosphorus Compounds; 0/Resin Cements; 1314-56-3/phosphorus pentoxide |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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