|
Sign In to gain access to subscriptions and/or personal tools.
|
Adsorption of Benzoic Acid on Pure and Cupric Ion-modified Hydroxyapatite: Implications for Design of a Coupling Agent to Dental Polymer Composites
D.N. Misra
American Dental Association Health Foundation, Paffenbarger Research Center, National Bureau of Standards, Gaithersburg, Maryland 20899
The adsorption isotherms of benzoic acid on synthetic hydroxyapatite (containing about 1.5 monolayers of physisorbed water) were studied from ethanol, dimethylsulfoxide, p-dioxane, methylene chloride, and benzene to discern the role of solvent in the process. The adsorption is reversible from the first three solvents and follows the Langmuir plots. It is irreversible from the last two, and a constant amount of absorbent is removed from solutions above a certain concentration. The isotherms of potassium benzoate on the apatite from ethanol and dimethyl sulfoxide were reversible.
The isotherms of the acid on cupric ion-modified apatite surfaces from ethanol and benzene were identical with those obtained on the pure hydroxyapatite. This may demonstrate that any "surface chelation" with the cation may not be a significant factor for adsorption to occur.
The adsorptive behavior seems to depend upon the interplay of hydrogen-bonding among the solute, the solvent, and the hydrated apatite surface. The capability of a solvent to hydrogen-bond may determine whether adsorption from it will be reversible or irreversible. Based upon its compatibility with a solvent, the benzene ring is upright or lies flat on the surface. The adsorbed molecules rotate about the center of the carboxylate groups which are hydrogen-bonded to the surface. These factors should be considered in designing or selecting a suitable surface-active moiety for a coupling agent between tooth mineral and a restorative resin.
REFERENCES
- Adamson, A.W. (1960): Physical Chemistry of Surfaces, New York, NY: Interscience, (a) p. 574, (b) p. 465.
- Bladon, J.J. (1980): Adsorption of Aqueous n-Alkyl Carboxylic and Dicarboxylic Acids onto Hydroxyapatite Simulated by a Lattice Adsorption Model, J Colloid Interface Sci 78:175-190.[CrossRef]
- Bowen, R.L.; Cobb, E.N.; and Rapson, J.E. (1982): Adhesive Bonding of Various Materials to Hard Tooth Tissues. Improvement in Bond Strength to Dentin, J Dent Res 61:1070-1076.[Abstract/Free Full Text]
- Dry, M.E. and Beebe, R.A. (1960): Adsorption Studies on Bone Mineral and Synthetic Hydroxyapatite, J Phys Chem 64:1300-1304.[CrossRef]
- Kiselev, A.V. and Uvarov, A.V. (1967): Infrared Spectra and Electron Spin Resonance of Aluminum, Silicon and Titanium Oxides and of Adsorbed Substances, Surf Sci 6:399-421.
- Kresak, M.; Moreno, E.C.; Zahradnik, R.T.; and Hay, D.I. (1977): Adsorption of Amino Acids onto Hydroxyapatite, J Colloid Interface Sci 59:283-292.
- Loebenstein, W.V. (1973): Adsorption of Water on Tooth Components and Related Materials, J Dent Res 52:271-280.[Abstract/Free Full Text]
- Misra, D.N.; Bowen, R.L.; and Wallace, B.M. (1975): Adhesive Bonding of Various Materials to Hard Tooth Tissues. VIII. Nickel and Copper Ions on Hydroxyapatite. Role of Ion Exchange and Surface Nucleation, J Colloid Interface Sci 51:36-43.[CrossRef]
- Misra, D.N. and Bowen, R.L. (1977a): Adhesive Bonding of Various Materials to Hard Tooth Tissues. XII. Adsorption of N-(2-hydroxy-3-methacryloxypropyl)-N-phenylglycine (NPG-GMA) on Hydroxyapatite, J Colloid Interface Sci 61:14-20.[CrossRef]
- Misra, D.N. and Bowen, R.L. (1977b): Adhesive Bonding of Various Materials to Hard Tooth Tissues. 11. Chemisorption of an Adduct (of the Diglycidyl Ether of Bisphenol A with N-Phenylglycine) on Hydroxyapatite, J Phys Chem 80:842-846.
- Misra, D.N. and Bowen, R.L. (1978): Adhesive Bonding of Various Materials to Hard Tooth Tissues. X. Initial Rates of Adsorption of Nickel or Copper Ions on Hydroxyapatite Surface, J Biomed Mater Res 12:505-515.[CrossRef][Medline]
[Order article via Infotrieve]
- Misra, D.N. and Bowen, R.L. (1981a): Adsorptive Bonding to Hydroxyapatite. I. Adsorption of Anthranilic Acid - the Effect of Solvents. Search for Surface Bonding Groups for Coupling Agents to Teeth, Biomaterials 2:28-32.[CrossRef][Medline]
[Order article via Infotrieve]
- Misra, D.N. and Bowen, R.L. (1981b): Adsorption of N-(2-hydroxy-3-methacryloxypropyl)-N-phenylglycine (NPG-GMA) on Cupric Ion-Enriched Hydroxyapatite Surface to Improve Chemical Bonding between Dental Resins and Teeth, Biomaterials 2:78-82.
- Misra, D.N. (1984): Adsorption of N,N-Dimethyl-p-aminophenyl Acetic Acid on Hydroxyapatite. In: Adsorption on and Surface Chemistry of Hydroxyapatite, D.N. Misra, Ed., New York, NY: Plenum Publishing Corporation, pp. 105-114.
- Misra, D.N. (1985): Adsorption of Zirconyl Methacrylate, Zirconyl-2-Ethylhexanoate and their Respective Acids on Hydroxyapatite: Use of the Salts as Coupling Agents to Dental Polymer Composites, J Dent Res 64:1405-1408.[Abstract/Free Full Text]
- Nakabayashi, N.; Masuhara, E.; Mochida, E.; and Ohmori, I. (1978): Development of Adhesive Pit and Fissure Sealants Using a MMA Resin Initiated by a Tri-n-Butyl Borane Derivative, J Biomed Mater Res 12:149-165.[CrossRef][Medline]
[Order article via Infotrieve]
- Nakabayashi, N.; Takeyama, M.; and Masuhara, E. (1982a): Adhesion of Poly(Methyl Methacrylate) (PMMA) Rod onto Hard Tissues. In: Biomaterials 1980, G. D. Winter, D. F. Gibbons, and H. Plenk, Jr., Eds., New York, NY: John Wiley and Sons, pp. 689-694.
- Nakabayashi, N.; Kojima, K.; and Masuhara, E. (1982b): The Promotion of Adhesion by the Infiltration of Monomers into Tooth Substrates, J Biomed Mater Res 16:265-273.[CrossRef][Medline]
[Order article via Infotrieve]
- Platzer, N.A.J. (Ed.) (1969): Addition and Condensation Processes, Washington, DC: American Chemical Society.
- Ritchie, C.D. and Uschold, R.E. (1968): Acidity in Nonaqueous Solvents. VI. Further Studies of Weak Acids in Dimethyl Sulfoxide Solution, J Am Chem Soc 90:2821-2844.
- Rochester, C.H. (1980): Infrared Studies of Adsorption at the Solid/Liquid Interface, Progr Colloid & Polymer Sci 67:7-17.
- Rootare, H.M. and Craig, R.G. (1978): Vapor Phase Adsorption of Water on Hydroxyapatite, J Dent Res 56:1437-1448.
- Schildknecht, C.E. and Skeist, I. (1977): Polymerization Processes, New York, NY: John Wiley & Sons.
- Tabagua, I.D.; Tsurtsumiya, M.M.; and Izmailov, N.A. (1962): Dissociation Constants of Some Carboxylic Acids in Ethanol and its Mixtures with Water, OTr. Sukhumsk Gas Ped Inst 15:108-18 (through Chem Abstr 60:1437h).
- Tamamushi, B. (1983): Factors Influencing the Adsorption from Solution, R. H. Ottewill, C. H. Rochester, and A. L. Smith, Eds., New York, NY: Academic Press, pp. 79-86.
- Voegel, J.C. and Frank, R.M. (1981): Adsorption of Benzene Carboxylic Acids onto Hydroxyapatite and Human Enamel Powder, J Colloid Interface Sci 83:26-34.[CrossRef]
- Voegel, J.C.; Gilmeth, S.; and Frank, R.M. (1981): Phosphate and Calcium Ion Release during Benzene Polycarboxylic Acid Adsorption onto Apatites. their Possible Role during the Adsorption Process, J Colloid Interface Sci 84:108-113.[CrossRef]
- Zahradnik, R.T. and Moreno, E.C. (1975): Structural Features of Human Dental Enamel as Revealed by Isothermal Water Vapor Sorption, Arch Oral Biol 20:317-325.[CrossRef][Medline]
[Order article via Infotrieve]
Journal of Dental Research, Vol. 65, No. 5,
706-711 (1986)
DOI: 10.1177/00220345860650051601

CiteULike Complore Connotea Del.icio.us Digg Reddit Technorati Twitter What's this?
This article has been cited by other articles:

|
 |

|
 |
 
D.N. Misra
Adsorption of Low-molecular-weight Sodium Polyacrylate on Hydroxyapatite
Journal of Dental Research,
October 1, 1993;
72(10):
1418 - 1422.
[Abstract]
[PDF]
|
 |
|

|
 |

|
 |
 
D.N. Misra
Adsorption of 4-Methacryloxyethyl Trimellitate Anhydride (4-META) on Hydroxyapatite and its Role in Composite Bonding
Journal of Dental Research,
January 1, 1989;
68(1):
42 - 47.
[Abstract]
[PDF]
|
 |
|
|
|