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WO1995007067A1 - Mordant liquide destine a lier des produits d'obturation a des tissus dentaires (email et dentine) - Google Patents

Mordant liquide destine a lier des produits d'obturation a des tissus dentaires (email et dentine) Download PDF

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Publication number
WO1995007067A1
WO1995007067A1 PCT/BY1993/000004 BY9300004W WO9507067A1 WO 1995007067 A1 WO1995007067 A1 WO 1995007067A1 BY 9300004 W BY9300004 W BY 9300004W WO 9507067 A1 WO9507067 A1 WO 9507067A1
Authority
WO
WIPO (PCT)
Prior art keywords
mordant
glycerophosphoric acid
dental
solution
filling material
Prior art date
Application number
PCT/BY1993/000004
Other languages
English (en)
Inventor
Aleksei D. Sidorik
Nikolai N. Grinchik
Original Assignee
Byelocorp Scientific, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Byelocorp Scientific, Inc. filed Critical Byelocorp Scientific, Inc.
Priority to PCT/BY1993/000004 priority Critical patent/WO1995007067A1/fr
Publication of WO1995007067A1 publication Critical patent/WO1995007067A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/30—Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives

Definitions

  • This invention relates to liquid mordants, more particularly to compounds useful for binding filling materials to dental tissues (enamel and dentin) .
  • Bond strength is composed of three types of bonds; mechanical retention, adhesion (i.e. electrical and intermolecular interactions) and chemical bonds between the filing material and tooth.
  • M.G. Buonocore disclosed a use of a surface treatment of 85 percent phosphoric acid to determine the effect on adhesion.
  • Buonocore "A Simple Method of Increasing the Adhesion of Acrylic Filling Materials to Enamel Surfaces," Journal of Dental Research, 34, 849-53 (1955) .
  • Buonocore describes an increased adhesion of acrylic filling materials to enamel using a phosphoric acid solution.
  • One disadvantage associated with the use of phosphoric acid in adhesion of dental fillings to tissue is that the acid typically is used in conjunction with other compositions, requiring a multi-step preparatory process. Furthermore, some of these compositions can be very toxic to the pulpa of a tooth.
  • 4,521,550, 4,588,756, 4,659,751 and 4,964,911 disclose the pretreatment of dental tissues with an acid or a salt solution with a low pH.
  • U.S. Patent 4,588,756 discloses that the preferred acid is nitric acid, but also describes that phosphoric acid or other acids might also be effective.
  • NPG N- phenylglycine
  • NGT-GMA N-(p-tolyl)glycine and glycidyl methacrylate
  • PMDM 2-hydroxyethyl methacrylate
  • BTDA-HEMA 3,3' ,4,4'-benzophenonetetracarboxylic dianhydride and 2- hydroxyethyl methacrylate
  • Phosphoric acid also is corrosive and difficult to use, especially when it is necessary to etch both the enamel and dentin of a tooth.
  • phosphoric acid is thought to be capable of penetrating into the dentin canaliculi to a substantial depth and injuring the dental pulpa.
  • phosphoric acid is usually not used on the dentin.
  • phosphoric acid is usually left on the dental enamel for sixty seconds.
  • a mordant capable of bonding dental filling materials and dental tissues. It is another object of this invention to provide a mordant which forms a chemical bond with dental tissue and filling materials and is resistant to water and mouth liquid. It is a further object of this invention to provide for improving the adhesion of dental filling materials to tissue which has a relatively low toxicity. It is another object of this invention to provide a mordant capable of etching enamel and dentin, without substantial damage to the dental pulpa. It is a further object of this invention to provide a process for adhering dental filling materials to tissue.
  • the invention also includes a method for treating dental tissue comprising forming a cavity for receiving a filling material; applying a liquid mordant comprising a solution of about 20% to 55% by weight glycerophosphoric acid in a solvent to an application area in the cavity consisting of (i) dental enamel or (ii) dental enamel and dentin; washing the application area; drying the application area; and adding a filling material to the cavity.
  • Both the alpha and beta isomers of glycerophosphoric acid can be active as a mordant, and a solution containing both isomers can be used with the invention. While not wishing to be bound by theory, it is believed that glycerophosphoric acid improves the bond strength of filling materials in two ways: 1) by changing the relief of the etching surface and 2) by causing tooth surfaces to become chemically bound with polymerizable filling materials (acrylic resins, polyacrylic cements, composite materials, etc.).
  • the glycerophosphoric acid of this invention allows bonding of filling materials to dental tissue with increased bond strength, lower toxicity, greater resistance to water and mouth liquids, and better affinity with dental tissues ("biochemical affinity") when compared with presently known methods of increasing bond strength.
  • Figure 1 is a cross-sectional view of a decayed tooth which has been bored in preparation for filling with a mordant of the invention.
  • Figure 2 is a cross-sectional view of a decayed tooth which is drilled at a 45° angle ⁇ in preparation for filling with a mordant of the invention.
  • Figure 3 is a cross-section of a tooth portion having a hook inserted in a filling material adhered with a mordant of the invention, useful for testing the bond strength of the filling.
  • a cavity is prepared for filling using conventional means in which a tooth is drilled, and then the area to be filled is cleaned and sterilized.
  • the tooth often is treated with one or more mordant solutions intended to increase the bond strength between a filling material to be added to the cavity and the surrounding dental tissue, though this step may not be necessary where mineral cements are employed as the filling material.
  • the filling material is added to the cavity.
  • the liquid mordant of the present invention comprises solution of about 20 to 55% by weight of glycerophosphoric acid in a suitable solvent. Distilled water is the most preferred solvent. In addition to glycerophosphoric acid and solvent, other suitable components can also be employed in the mordant, such as gelatinizing additives or other additives which do not interfere substantially with the adhesive qualities of the mordant.
  • the most preferred embodiment of the invention comprises a 30% by weight solution of glycerophosphoric acid in distilled water.
  • the solution is capable of increasing the strength of the bond between filling materials and dental tissues by providing a chemical link between the filling material and dental tissues.
  • Glycerophosphoric acid has a relatively low toxicity to healthy dental tissue, and therefore is desirable for this purpose. As compared with phosphoric acid, glycerophosphoric acid is less toxic for several reasons. First, glycerophosphoric acid is not as strong as phosphoric acid. Also, due to its high ability to absorb moisture, glycerophosphoric acid does not penetrate deeply into the dentin canaliculi and therefore is not as injurious to the dental pulpa. In addition, glycerophosphoric acid need only be applied to the cavity area for shorter periods of time to be effective, as compared to phosphoric acid.
  • glycerophosphoric acid has a relatively good ability to absorb moisture, it can be used for etching not only enamel, but also dentin without danger of significantly damaging the dental pulpa.
  • the dentin canaliculi can contain microorganisms which decay the dentin and pulpa.
  • a glycerophosphoric acid solution is applied to the dentin surface, the solution absorbs fluid from the canaliculi, and the fluid flows onto the dentin surface. The fluid washes the microorganisms out of the canaliculi and decreases the levels of harmful bacteria in the dentin. Since the fluid flow is directed from the dentin to the surface, glycerophosphoric acid should not penetrate significantly into the canaliculi or cause significant injury to the pulpa.
  • R and R 1 each are molecules of a filling material.
  • One active bonding site is at the acidic groups which bind with the calcium atoms of dental tissue. This reaction is believed to occur relatively quickly and substantially completely due to its biochemical affinity with dental tissues. The reaction can take place in about thirty seconds in preferred embodiments, and its speed and completeness can contribute to lower toxicity of the mordant.
  • the calcium salt which results from the reaction is substantially insoluble, and resists both water and mouth liquids.
  • the alcohol radical is believed to be highly reactive and capable of bonding with many suitable filling resins.
  • suitable filling resins may be, for example, polyacrylic cements, acrylic resins (including cyanaerylic polymers) , epoxy resins, and polyurethane resins.
  • suitable filling materials believed to be capable of bonding with the alcohol radical are polycarboxylic cements, acryloxide, and filling resins sold under the trade names Evicrol (in Czechoslovakia) , Vivadent (in Germany) , Carêtt (in the Ukraine) , and Microrest (in Japan) .
  • the bonds produced at the alcohol radical can be ether bonds or ester bonds, depending on the composition of the filling material, as shown below:
  • the glycerophosphoric acid of the present invention can be produced by methods known to one skilled in the art.
  • One method of producing glycerophosphoric acid comprises heating a mixture of concentrated (76%) solution of orthophosphoric acid in water with glycerin at a 1:1 molar ratio. At the boiling temperature of the mixture, which typically is approximately 178°C, the combination will yield a golden-colored syrupy liquid, which is subsequently diluted to a 30% solution by weight by the addition of distilled water. The color is believed to be caused by small amounts of impurities present in glycerin. When very pure (distilled) glycerin is used, the final product is practically colorless. If gelatinized additives are included, they preferably are added after dilution of the glycerophosphoric acid to the desired concentration.
  • Glycerophosphoric acid also can be produced by heating a mixture of crystalline phosphoric acid and glycerin to a temperature of 110°C.
  • Each of these processes yields a mixture of alpha and beta isomers of glycerophosphoric acid, each of which is equally active in increasing the bond strength of dental fillings.
  • the mordant comprises both isomers.
  • the isomers can be separated, and only one isomer can be employed in the composition. Where the mordant contains only one isomer, a mixture of a and ⁇ isomers can be produced using the processes described above, and can then be separated.
  • a suitable compound used for separation of the isomers is barium nitrate, which reacts with ⁇ glycerophosphoric acid to produce the hard soluble salt 2C 3 H 7 0 6 PBa.Ba(N0 3 ) 2 .
  • a decayed tooth can be treated according to the invention as follows. First, a caries cavity can be drilled, as shown in Figure 1, with the area drilled 4 extending through the enamel 1 and into the dentin 2, but not to the pulpa 3. Where only the enamel portion of the tooth is to be treated with glycerophosphoric acid, it may be desirable to increase the contact area of the acid to the tissue by drilling the dental cavity at 45 degrees a as shown in Figure 2.
  • ethyl alcohol which sometimes is used for treatment of decay cavities as an antiseptic and drying agent.
  • the alcohol can dehydrogenate the dental canaliculi.
  • Ethyl alcohol has a relatively high ability to absorb moisture and induces the same processes in the dentin canaliculi as glycerophosphoric acid. If an ethyl alcohol pretreatment is followed by glycerophosphoric acid application to the dentin, there is a possibility that glycerophosphoric acid may flow into dry canaliculi and injure the pulpa.
  • a mordant comprising a solution of glycerophosphoric acid is applied to the dental tissue.
  • a solution containing a concentration of approximately 30% by weight glycerophosphoric acid is applied to dental tissue.
  • the solution preferably is a mixture of the alpha and beta isomers of glycerophosphoric acid.
  • the amount of solution should be sufficient to apply a thin layer covering the whole surface being etched, and typically is ⁇ about 1 to 3 drops.
  • the solution can be applied by a brush, cotton ball, or a dentist's ordinary tools, such as a spatula or probe.
  • a suitable bonding time is then permitted to elapse, preferably about 30 seconds.
  • the cavity can then be washed out, preferably by water, such as through use of a water jet.
  • the dental cavity can then be dried, such as by an air jet.
  • glycerophosphoric acid can be reapplied, preferably for a shorter period than the initial application, and more preferably for about 10 seconds. The cavity can then be washed out and dried, as with the first application.
  • etching of dental tissues with glycerophosphoric acid solution in this manner can result in a greater bond strength of acrylic resin, polyacrylic, and other filling composites to dental tissues.
  • a suitable filling material can be added to the cavity and permitted to bond with the dental tissue using the mordant.
  • Example 1 An amount of 30% glycerophosphoric acid solution sufficient to apply a thin layer covering the whole surface being etched was applied to a tooth surface that had been prepared for filling using conventional drilling means. After application of the solution, a total of thirty seconds passed, and the surface was washed out using a water flow and dried by an air jet. Next, the tooth was filled with acryloxide, a filling composite produced by Kharkov Factory of Medical Plastics and Dentistry Materials, the Ukraine.
  • the acryloxide was made by combining (a) a powder composition comprised of methylmethacrylate, buthylmethacrylate, powdered quartz, benzoyl peroxide, sodium benzolsulfonate, titanium dioxide, and pigments, and (b) a liquid comprised of methylmethacrylate, methacrylic acid and ED-16 epoxy resin adduct, dimethylparatolundin, ethyl alcohol and hydroxinone.
  • a hook 1 was embedded into the filling material 2, after which the tooth 3 was chemically hardened, or cured, for a period of 8 to 10 minutes. The specimen was then kept in water for three days.
  • the bond strength of the filling to the tooth then was measured by extracting the filling material from the tooth surface using the hook.
  • the force used to disrupt the filling material was considered a measure of the bond strength.
  • the bond strength was 21.5 ⁇ 1.4 kg/cm 2 .
  • Example 2 An amount of 30% glycerophosphoric acid solution sufficient to apply a thin layer covering the whole surface being etched was applied to a tooth surface that had been prepared for filling using conventional drilling means. After application of the solution, a total of about thirty seconds passed, and the surface was washed out using a water flow and dried by air jet. Next, the tooth was filled with a polycarboxylate cement, a commercial product of the Kharkov Factory of Medical Plastics and Dentistry Materials, the Ukraine.
  • the polycarboxylate cement was made from a powder comprised of (a) zinc oxide thermally treated by heating to about 1000 °C, with a relatively small amount of magnesium oxide, and (b) a liquid consisting of concentrated water solution of polyacrylic acid.
  • a hook such as is depicted in Figure 3, was embedded into the filling material after which the tooth was cured for a period of 8 to 10 minutes. The specimen was then kept in water for three days.
  • the bond strength was measured by detaching the filling material from the tooth surface, in the same manner as Example 1, for a series of trials.
  • the bond strength was determined to be 22 ⁇ 1.3 kg/cm 2 .
  • Comparative Example 1 A tooth surface was filled with acryloxide, using no mordant. After curing, the specimen was kept in water for three days. The bond strength then was measured by detaching the filling material from the tooth surface in the same manner as Example 1 for a series of trials. The bond strength was determined to be 1.4 ⁇ 0.9 kg/cm 2 ,
  • Comparative Example 2 A tooth surface was filled with polycarboxylate cement, using no mordant. After curing, the specimen was kept in water for three days. The bond strength then was measured by detaching the filling material from the tooth surface in the same manner as Example 1 for a series of trials. The bond strength was determined to be 2.1 ⁇ 0.8 kg/cm 2 .

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  • Health & Medical Sciences (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dental Preparations (AREA)

Abstract

Mordant liquide qui comprend une solution d'acide glycérophosphorique dans un solvant, et procédé de traitement de tissus dentaires à l'aide dudit mordant liquide. Ledit mordant comprend de préférence une solution contenant d'environ 20 à 55 % en poids d'acide glycérophosphorique dans de l'eau distillée. L'acide glycérophosphorique modifie le relief de la surface à attaquer du tissu dentaire, ce qui donne à la liaison une plus grande résistance qu'avec les procédés classiques, tout en maintenant une toxicité réduite.
PCT/BY1993/000004 1993-09-10 1993-09-10 Mordant liquide destine a lier des produits d'obturation a des tissus dentaires (email et dentine) WO1995007067A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/BY1993/000004 WO1995007067A1 (fr) 1993-09-10 1993-09-10 Mordant liquide destine a lier des produits d'obturation a des tissus dentaires (email et dentine)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/BY1993/000004 WO1995007067A1 (fr) 1993-09-10 1993-09-10 Mordant liquide destine a lier des produits d'obturation a des tissus dentaires (email et dentine)

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WO1995007067A1 true WO1995007067A1 (fr) 1995-03-16

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS53113843A (en) * 1977-03-15 1978-10-04 Kuraray Co Ltd Adhesive for rigid tissue
US4802950A (en) * 1988-04-12 1989-02-07 Croll Theodore P Enamel-bonding etchant and procedure
JPH05117157A (ja) * 1991-09-04 1993-05-14 Kao Corp 象牙質知覚過敏予防・治療剤及びこれを含有する口腔用組成物
US5244651A (en) * 1991-09-04 1993-09-14 Kao Corporation Method of desensitizing hypersensitive dentin

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS53113843A (en) * 1977-03-15 1978-10-04 Kuraray Co Ltd Adhesive for rigid tissue
US4802950A (en) * 1988-04-12 1989-02-07 Croll Theodore P Enamel-bonding etchant and procedure
JPH05117157A (ja) * 1991-09-04 1993-05-14 Kao Corp 象牙質知覚過敏予防・治療剤及びこれを含有する口腔用組成物
US5244651A (en) * 1991-09-04 1993-09-14 Kao Corporation Method of desensitizing hypersensitive dentin

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Week 7845, Derwent World Patents Index; Class A81, AN 78-81153A *
DATABASE WPI Section Ch Week 9324, Derwent World Patents Index; Class A96, AN 93-191438 *

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