title: Synthesis of phosphate monomers and bonding to dentin: esterification methods and use of phosphorus pentoxide.
abstract: OBJECTIVE
  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.
  
  
  CONCLUSIONS
  The synthesis pathways described in the present study appear to be a viable alternative for developing phosphate monomers.
authors.affiliation: Operative Dentistry Department, School of Dentistry, Federal University of Pelotas, RS, Brazil.
authors.forename: Fabrício Aulo
authors.initials: FA
authors.lastname: Ogliari
authors.forename: Eduardo de Oliveira
authors.initials: Ede O
authors.lastname: da Silva
authors.forename: Giana da Silveira
authors.initials: Gda S
authors.lastname: Lima
authors.forename: Francine Cardozo
authors.initials: FC
authors.lastname: Madruga
authors.forename: Sandrina
authors.initials: S
authors.lastname: Henn
authors.forename: Márcia
authors.initials: M
authors.lastname: Bueno
authors.forename: Marco Antônio
authors.initials: MA
authors.lastname: Ceschi
authors.forename: Cesar Liberato
authors.initials: CL
authors.lastname: Petzhold
authors.forename: Evandro
authors.initials: E
authors.lastname: Piva
mesh_terms: D000134:Acid Etching, Dental / Q000379:methods; D000704:Analysis of Variance; D000818:Animals; D002417:Cattle; D001840:Dental Bonding; D003799:Dental Stress Analysis; D003804:Dentin; D003806:Dentin Permeability; D017220:Dentin-Bonding Agents / Q000138:chemical synthesis; D004951:Esterification; D009682:Magnetic Resonance Spectroscopy; D008422:Materials Testing; D008689:Methacrylates / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D017553:Phosphorus Compounds / Q000138:chemical synthesis / Q000737:chemistry; D019279:Resin Cements / Q000138:chemical synthesis; D017550:Spectroscopy, Fourier Transform Infrared; D013718:Tensile Strength
chemical_list: D017220:Dentin-Bonding Agents; D008689:Methacrylates; D017553:Phosphorus Compounds; D019279:Resin Cements; C012500:phosphorus pentoxide