DE3024944A1 - 2-Phosphato-ethyl polymethacrylate addn. to dental cement compsn. - increases strength and adhesion to dentine and lowers solubility in water or lactic acid - Google Patents

2-Phosphato-ethyl polymethacrylate addn. to dental cement compsn. - increases strength and adhesion to dentine and lowers solubility in water or lactic acid

Info

Publication number
DE3024944A1
DE3024944A1 DE19803024944 DE3024944A DE3024944A1 DE 3024944 A1 DE3024944 A1 DE 3024944A1 DE 19803024944 DE19803024944 DE 19803024944 DE 3024944 A DE3024944 A DE 3024944A DE 3024944 A1 DE3024944 A1 DE 3024944A1
Authority
DE
Germany
Prior art keywords
cement
dental
phosphato
dentine
lactic acid
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
DE19803024944
Other languages
German (de)
Other versions
DE3024944C2 (en
Inventor
Abraham Antonius Dr. Driessen
Klaas de Prof. Heemstede Groot
Anthony Cornelis de Heiloo Visser
Joop Dr. Amsterdam Wolke
Koog van der Zaan
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Richter & Hoffmann Harvard Den
Original Assignee
Richter & Hoffmann Harvard Den
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 Richter & Hoffmann Harvard Den filed Critical Richter & Hoffmann Harvard Den
Priority to DE3024944A priority Critical patent/DE3024944C2/en
Publication of DE3024944A1 publication Critical patent/DE3024944A1/en
Application granted granted Critical
Publication of DE3024944C2 publication Critical patent/DE3024944C2/en
Expired legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00Preparations for dentistry
    • A61K6/40Primers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00Preparations for dentistry
    • A61K6/80Preparations for artificial teeth, for filling teeth or for capping teeth
    • A61K6/849Preparations for artificial teeth, for filling teeth or for capping teeth comprising inorganic cements
    • A61K6/86Al-cements
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00Preparations for dentistry
    • A61K6/80Preparations for artificial teeth, for filling teeth or for capping teeth
    • A61K6/849Preparations for artificial teeth, for filling teeth or for capping teeth comprising inorganic cements
    • A61K6/864Phosphate cements
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00Preparations for dentistry
    • A61K6/80Preparations for artificial teeth, for filling teeth or for capping teeth
    • A61K6/849Preparations for artificial teeth, for filling teeth or for capping teeth comprising inorganic cements
    • A61K6/871Quartz; SiO2
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00Preparations for dentistry
    • A61K6/80Preparations for artificial teeth, for filling teeth or for capping teeth
    • A61K6/849Preparations for artificial teeth, for filling teeth or for capping teeth comprising inorganic cements
    • A61K6/878Zirconium oxide

Abstract

In the prodn. of dental cements, consisting of a mixt. of metal oxides and stirring fluid, 1-15 (2-5)% (2-phosphato-ethyl) poly-methacrylate, (I), is added to the stirring fluid or cement powder. The metal oxides can be ZnO and/or MgO, Al oxide or SiO2. Main stirring fluid component can be H3PO4 or a polycarboxylic acid, e.g. an acrylic acid homo- or copolymer. The dental cements can be used to fix crowns, inlays, as sub-fillings in dental prostheses and as filling material. (I)-addn. improves adhesion to dentine, lowers solubility in water or lactic acid and prevents colouring material- and bacteria penetration in cement. Dental cement compressive- and tensile strength are improved.

Description

Die Erfindung betrifft ein Verfahren zur HerstellungThe invention relates to a method of manufacture

von Zahnzementen gemäß dem Oberbegriff des Anspruchs.of dental cements according to the preamble of the claim.

In der Zahnmedizin findet für verschiedene Verwendungszwecke eine Reihe von Zementen Anwendung, und zwar beispielsweise zum Befestigen von Kronen und Inlays sowie zahnorthopädischen Apparaten als Unterfüllung zum chutz der Zahnpulpa gegen chemische oder physikalische Angriffe unter einem anderen Füllungsmaterial oder auch als Füllmaterial für Zahnkavitäten selbst.In dentistry there is one for various purposes A range of cements used, for example for fastening crowns and inlays as well as orthodontic appliances as underfilling to protect the tooth pulp against chemical or physical attacks under another filling material or as a filling material for tooth cavities themselves.

Die Zemente bestehen in der Regel aus einer Mischung von Metalloxiden, die mit einer AnriThrflüssigkeit, die als Hauptbestandteile Phosphorsäure oder Polycarbonsäure enthält, zur Reaktion gebracht wird.The cements usually consist of a mixture of metal oxides, those with a mixing liquid, the main components of which are phosphoric acid or polycarboxylic acid contains, is made to react.

Solche Zemente haben sich seit Jahrzehnten in der zahnärztlichen Praxis gut bewährt. Sie zeichnen sich durch gute Verarbeitungseigenschaften, schnelles Abbinden und ausreichende Festigkeit aus und erfüllen oft Jahre oder Jahrzehnte lang ihre Aufgabe.Such cements have been used in dental practice for decades well proven. They are characterized by good processing properties, fast Setting and sufficient strength and often fulfilling years or decades long their task.

Nachteilig ist jedoch, daß die Zemente spröde sind, daß sie keine Kantenfestigkeit besitzen, daß sie nach ihrer Zusammensetzung schädigend auf die Pulpa einwirken können, daß sie meist nach einiger Zeit von den Nündflüssigkeiten, insbesondere den Milchsäurebakterien, angegriffen werden und daß sie keine genügende Haftung an der Zahnsubstanz oder an den zu befestigenden Metallen aufweisen.However, the disadvantage is that the cements are brittle that they are not Edge strength have that they are damaging to the composition according to their composition Pulp can act so that after some time it is usually removed from the nursing fluids, especially the lactic acid bacteria, are attacked and that they are insufficient Have adhesion to the tooth substance or to the metals to be attached.

Der Erfindung liegt die Aufgabe zu Grunde, die Eigenschaften dieser Zahnzemente zu verbessern.The invention is based on the object, the properties of these To improve dental cements.

Gelöst wird diese Aufgabe dadurch, daß erfindungsgemäß dem Zahnzement oder der Anrührflüssigkeit 1-15%, vorzugsweise 2-5% (2-Phosphato-ethyl)polymethacrylat zugesetzt wird.This object is achieved in that, according to the invention, the dental cement or the mixing liquid 1-15%, preferably 2-5% (2-phosphato-ethyl) polymethacrylate is added.

Untersuchungen an in dieser Weise hergestellten Zahnzementen haben ergeben, daß abgesehen von wesentlich verbesserten Druck- und Zugfestigkeiten, insbesondere die Haftungseigenschaften am Dentin verbessert worden sind bzw. überhaupt erst eine Haftung erreicht wurde, daß die Löslichkeit in Wasser bzw. in Milchsäure erheblich gesenkt und das Eindringen von Farbstoffen bzw. Bakterien in den Zement verhindert wird.Have investigations on dental cements produced in this way show that apart from significantly improved compressive and tensile strengths, in particular the adhesion properties to the dentin have been improved or even one in the first place Adhesion has been achieved that the solubility in water or in lactic acid is considerable and prevents the penetration of dyes or bacteria into the cement will.

Die Erfindung soll nachfolgend anhand von Beispielen erläutert werden.The invention is to be explained below on the basis of examples.

Zunächst ist die Herstellung des erfindungsgemäßen Zahnzementes beschrieben.First, the production of the dental cement according to the invention is described.

Bei der Herstellung des Polymers wird ausgegangen von einem 2-Hydroxyethylmethacrylat. Dieses wurde mit äquimolaren Mengen von Phosphorpentoxid in Diethyläther bei 5 bis lO0C zur Reaktion gebracht.The production of the polymer is based on a 2-hydroxyethyl methacrylate. This was with equimolar amounts of phosphorus pentoxide in diethyl ether at 5 to 10 ° C brought to reaction.

Nach einer Reinigung mittels herkömmlicher Methoden (wiederholtes Waschen mit Diethyläther) wurde eine viskose farblose Flüssigkeit erhalten. Dieses Produkt bestand aus einer Mischung von Mono- und Diester der Phosphorsäure. Nach einer Lösung in in Methanol wurden 0,2 Gew.-% Methyl- bis Isobutyrat als Polymerisationsauslöser zugesetzt. Die Polymerisation lief über 12 Stunden bei 600C. Das erhaltene Polymer wurde gefällt, in Diethyläther wiederholt aufgelöst und filtriert um unlösbaere Anteile zu entfernen.After cleaning using conventional methods (repeated Washing with diethyl ether) a viscous colorless liquid was obtained. This Product consisted of a mixture of mono- and diesters of phosphoric acid. To a solution in 0.2% by weight of methyl bis isobutyrate was found in methanol added as a polymerization trigger. The polymerization proceeded over 12 hours 600C. The polymer obtained was precipitated and repeatedly dissolved in diethyl ether and filtered to remove insoluble parts.

Zur Herstellung des Zahnzementes wurden Jeweils 2,5 bzw. 5 g dieses Polymers in 100 g der Zementflüssigkeit gelöst. Das Polymer kann aber auch in Form eines Salzes mit dem Zementpulver vermischt werden. Zementflüssigkeit und Zementpulver werden vom Zahnarzt in bekannter Weise gemischt und je nach Anwendungszweck eingesetzt.To produce the dental cement, 2.5 and 5 g of it were used in each case Polymer dissolved in 100 g of the cement liquid. But the polymer can also be in the form of a salt are mixed with the cement powder. Cement liquid and cement powder are mixed by the dentist in a known manner and used depending on the application.

Aus der nachfolgenden Tabelle 1 ist ersichtlich, daß mit steigendem Anteil des Polymers, die Eigenschaften des Zementes wesentlich verbessert werden.From the following table 1 it can be seen that with increasing Proportion of the polymer, the properties of the cement are significantly improved.

Tabelle 1 *)Brasilian test. Drucklfestig- Zugfestig- Haftung keit keit*) am Dentin MPa MPa MPa ZinkphosPhatzement -. 97,92,6 4,211,25 0,42 0,11 (standard) Zinkphosphatzement 110,6 + 2,8 3,60 + 0,84 1,83 + 0,22 (+ 2 1/2% polymer) Zinkphosphatzement (+ 5% polymer) 124,2 + 2,2 5,93 + 2,0 4,35 + 1,20 Carboxylatzement (standard) 78,8 + 5,7 1,8 + 0,76 2,31 + 0,76 Carboxylatzement (+ 2 1/296 polymer) 100,3 + 4,5 2,36 + o,48 2,97 + 0,32 Carboxylatzement (+ 5% polymer) 100,8 + 5,0 4,69 + 1,18t 4,06 + 0,57 Tabelle 2 Zinkphosphatzement Zinkphoshat- zement (standard) (+ 5% polymer) Löslichkeit (7 Tage: Rest. Wasser 37 0,1% c in %Gew.Verlust 0,1% 0% Angreifbar- keit (7 Std. in 1/50 N Milchsäure in mm Erosionstie- 4,6 + 0,61 0,2 + 0,04 fe Table 1 *) Brazil test. Compressive strength, tensile strength, adhesion ability *) on dentine MPa MPa MPa Zinc phosphate cement -. 97.92.6 4.211.25 0.42 0.11 (default) Zinc phosphate cement 110.6 + 2.8 3.60 + 0.84 1.83 + 0.22 (+ 2 1/2% polymer) Zinc phosphate cement (+ 5% polymer) 124.2 + 2.2 5.93 + 2.0 4.35 + 1.20 Carboxylate cement (standard) 78.8 + 5.7 1.8 + 0.76 2.31 + 0.76 Carboxylate cement (+ 2 1/296 polymer) 100.3 + 4.5 2.36 + o.48 2.97 + 0.32 Carboxylate cement (+ 5% polymer) 100.8 + 5.0 4.69 + 1.18t 4.06 + 0.57 Table 2 Zinc phosphate cement zinc phosphate cement (standard) (+ 5% polymer) solubility (7 days: rest. Water 37 0.1% c in% weight loss 0.1% 0% Vulnerable- ability (7 hours in 1/50 N lactic acid in mm depth of erosion - 4.6 + 0.61 0.2 + 0.04 fe

Claims (1)

Zahnzement Patentanspruch Verfahren zur Herstellung von Zahnzementen, bestehend aus einer Mischung von Metalloxiden, beispielsweise Zinkoxid und/oder Magnesiumoxid Aluminiumoxid, Siliziumoxid und einer Anrührflüssigkeit, deren Hauptbestandteil entweder Phosphorsäure oder eine Polycarbonsäure, wie ein Homopolymerisat oder Copolymerisat der Acrylsäure ist, dadurch gekennzeichnet, daß der Anrührflüssigkeit oder dem Zementpulver 1-15%, vorzugsweise 2-596 (2-Phosphato-ethyl)poly-methacrylat zugesetzt ird.Dental cement Patent claim Process for the production of dental cements, consisting of a mixture of metal oxides, for example zinc oxide and / or Magnesium oxide Aluminum oxide, silicon oxide and a mixing liquid, their main component either phosphoric acid or a polycarboxylic acid, such as a homopolymer or copolymer of acrylic acid, characterized in that the mixing liquid or the cement powder 1-15%, preferably 2-596 (2-phosphato-ethyl) poly-methacrylate is added.
DE3024944A 1980-06-27 1980-06-27 Dental cement Expired DE3024944C2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE3024944A DE3024944C2 (en) 1980-06-27 1980-06-27 Dental cement

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE3024944A DE3024944C2 (en) 1980-06-27 1980-06-27 Dental cement

Publications (2)

Publication Number Publication Date
DE3024944A1 true DE3024944A1 (en) 1982-02-11
DE3024944C2 DE3024944C2 (en) 1984-02-16

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Family Applications (1)

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Country Status (1)

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DE (1) DE3024944C2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0106442A2 (en) * 1982-08-24 1984-04-25 National Research Development Corporation Fluoride-containing compositions

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
NICHTS-ERMITTELT *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0106442A2 (en) * 1982-08-24 1984-04-25 National Research Development Corporation Fluoride-containing compositions
EP0106442A3 (en) * 1982-08-24 1985-05-29 National Research Development Corporation Fluoride-containing compositions
US4732617A (en) * 1982-08-24 1988-03-22 National Research Development Corporation Fluoride-containing compositions

Also Published As

Publication number Publication date
DE3024944C2 (en) 1984-02-16

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