EP2180870A2 - Dental material - Google Patents

Dental material

Info

Publication number
EP2180870A2
EP2180870A2 EP08772586A EP08772586A EP2180870A2 EP 2180870 A2 EP2180870 A2 EP 2180870A2 EP 08772586 A EP08772586 A EP 08772586A EP 08772586 A EP08772586 A EP 08772586A EP 2180870 A2 EP2180870 A2 EP 2180870A2
Authority
EP
European Patent Office
Prior art keywords
polymeric
dental material
material according
guanidine derivative
oxyalkylenediamine
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.)
Withdrawn
Application number
EP08772586A
Other languages
German (de)
French (fr)
Inventor
Christa Hametner
Oskar Schmidt
Christoph Schmidt
Christine Diefenbach
Albert Erdrich
Theresa Puchalska
Karl Heinz Renz
Klaus Ruppert
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.)
Geopharma Produktions GmbH
Original Assignee
Geopharma Produktions GmbH
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 Geopharma Produktions GmbH filed Critical Geopharma Produktions GmbH
Publication of EP2180870A2 publication Critical patent/EP2180870A2/en
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
    • A61L24/0047—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material
    • A61L24/0073—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material with a macromolecular matrix
    • A61L24/0094—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material with a macromolecular matrix containing macromolecular fillers
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/70—Preparations for dentistry comprising inorganic additives
    • A61K6/71—Fillers
    • A61K6/76—Fillers comprising silicon-containing compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
    • A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
    • A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
    • A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
    • A61K6/891—Compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/90—Compositions for taking dental impressions

Definitions

  • the present invention relates to a polymeric dental material having microbiocidal activity.
  • polymeric dental materials in particular those based on (meth) acrylate, tend to form plaque with prolonged use and poor dental hygiene. Attempts have been made to reduce the harmful plaque formation and also the risk of infection by adding a biocidal active substance.
  • the biocidic agent is a polymeric condensation product formed from a guanidine derivative and an oxyalkylene diamine.
  • Such polymeric guanidine derivatives are e.g. from WO 01/85676 A1, AT 406 163 B and WO 06/047800.
  • biocidal active substance can be washed out of the dental material over time, whereby the plaque formation is favored again.
  • This object is achieved according to the invention with a polymeric dental material containing a siliceous filler which is modified with a polymeric guanidine derivative based on an alkylenediamine and / or an oxyalkylenediamine.
  • the invention is based on the surprising observation that these polymeric guanidine derivatives bind so strongly to silicates that they are practically no longer soluble in water, from the dental material can not be washed out, but still have the microbiocidal effect.
  • Silastic fillers for polymers are known per se. Now, when these fillers are modified with the polymeric guanidine derivative and incorporated into the polymer, they impart the plaque-inhibiting property to the polymer, although they are tightly bound to the siliceous filler.
  • a preferred embodiment of the polymeric dental material according to the invention is characterized in that a polymeric guanidine derivative is provided which contains the alkylenediamine and the oxyalkylenediamine in a molar ratio of between 4: 1 and 1: 4.
  • the amino groups of the alkylenediamine and / or the oxyalkylenediamine are preferably terminal, wherein for the preparation of the polymeric guanidine derivative as the alkylenediamine in the first place, a compound of the general formula
  • n is an integer between 2 and 10, in particular 6, is.
  • polymeric guanidine derivative for the preparation of the polymeric guanidine derivative can as oxyalkylene diamine a compound of the general formula
  • n is an integer between 2 and 5, in particular 2.
  • a polymeric dental material which is characterized in that a polyoxyalkylene guanidine based on triethylene glycol diamine (relative molecular mass: 148), of polyoxypropylene diamine (relative molecular mass: 230) and / or of polyoxyethylene diamine (relative molecular mass: 600) is used as the polymeric guanidine derivative. is provided.
  • silicate filler in which is provided as the polymeric guanidine derivative poly [2- (2-ethoxyethoxyethyl) guanidinium hydrochloride] having at least 3 guanidine residues.
  • the polymeric guanidine derivative has an average molecular weight in the range of 500 to 3,000.
  • the filler may be contained in an amount between 0.05 and 5.0 wt .-%.
  • the polymer is a curable plastic, preferably based on acrylate or methacrylate.
  • silicate filler is not only powdery SiO 2 , but also finely divided silicas and other silicates, especially those that are used today as fillers in plastics technology.
  • the binding of the polymeric guanidine derivative (active ingredient) to the siliceous filler, that is to say the carrier matrix, takes place by presentation of the matrix, which consists, for example, of fine Aerosil Types may exist and mixing a 1-30% Gew. - aqueous solution of the active ingredient at room temperature in a stirred tank.
  • the water can then be removed using conventional technologies, such as fluid bed dryers.
  • the matrix-bound active substance in this form is still very effective against microorganisms, but it is so strongly bound to the filler that it is virtually insoluble in water and can be washed out.
  • the described matrix fixation of the active ingredient thus prevents the migration of the active ingredient in aqueous media. Migration into fatty media is also not possible due to the insolubility of the polar agent.
  • dental materials in a broader sense are suitable, including materials used in the field of orthodontics or maxillofacial surgery or dental cosmetics / aesthetics.
  • materials used in the field of orthodontics or maxillofacial surgery or dental cosmetics / aesthetics are e.g. Filling composites, K & B veneering plastics (for crown and bridge), denture resins, dentin bonding, impression materials, impression trays, temporary K & B materials, implants, dental equipment, dental braces or ligaments, bone cements for maxillofacial surgery and applications for it.
  • Versyo.com is made from the following components with the appropriate weight fractions: a.) Urethane dimethacrylate 90.0 b.) Polyester arethane acrylate 15.0 c.) Oligoether tetraacrylate 13.5 d.) Trimethylopropane trimethacrylate 12.0 e.) Ethoxylated bis-GMA 7, 5 ⁇ f.) Pyrogenic SiO 2 10.5 g.) Photoinitiators / stabilizers 0.75 h.) Color pigments 0.009 The components are homogenized and then polymerized with a suitable light device.
  • Versyo.com + 0.5% bound active ingredient is prepared from the following components with the appropriate proportions by weight: a.) Urethane dimethacrylate 90.0 b.) Polyester urethane acrylate 15.0 c) oligoether tetraacrylate 13.5 d.) Trimethylopropane trimethacrylate 12.0 e.) Ethoxylated bis-GMA 7.5 f.) Pyrogenic SiO2 9.75 g.) Biocidal guanidine derivative 0.75 h.) Photoinitiators / stabilizers 0.75 i.) Color pigments 0.009
  • the bound active ingredient used according to the invention was used in the Versio.com acrylate mixture in use concentrations between 0.25 and 0.75 wt .-% and then the effectiveness of the test bacteria Streptococcus mutans DSM 20523 and Candida albicans DSM 1386 using the method JIS Z 2801 2000 tested on the plastic surface, the samples were eluted for up to 26 weeks at 37 ° C in ultrapure water with constant shaking in a ratio of 1: 1 (cm 2 xm 3 ).

Landscapes

  • Health & Medical Sciences (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Chemical & Material Sciences (AREA)
  • Plastic & Reconstructive Surgery (AREA)
  • Engineering & Computer Science (AREA)
  • Composite Materials (AREA)
  • Materials Engineering (AREA)
  • Surgery (AREA)
  • Inorganic Chemistry (AREA)
  • Dental Preparations (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

The invention relates to a polymeric dental material, characterized in that said polymeric material contains a silicate filler which is modified with a polymeric guanidine derivative on the basis of an alkylene diamine and/or an oxyalkylene diamine.

Description

Dentalwerkstoff Dental material
Die vorliegende Erfindung betrifft einen polymeren Dentalwerkstoff mit mikrobiozider Wirkung.The present invention relates to a polymeric dental material having microbiocidal activity.
Es ist bekannt, dass polymere Dentalwerkstoffe, insbesondere solche auf (Meth)acrylat-Basis, bei längerer Verwendung und mangelhafter Zahnhygiene zur Plaque-Bildung neigen. Es ist versucht worden, durch Zugabe eines bioziden Wirkstoffes die schädliche Plaque-Bildung und auch die Infektionsgefahr zu vermindern. Bei dem bioziden Wirkstoff handelt es sich um ein polymeres Kondensationsprodukt, welche aus einem Guanidinderivat und einem Oxyalkylendiamin gebildet wird. Derartige polymere Guanidinderivate sind z.B. aus der WO 01/85676 Al, der AT 406.163 B und der WO 06/047800 bekannt.It is known that polymeric dental materials, in particular those based on (meth) acrylate, tend to form plaque with prolonged use and poor dental hygiene. Attempts have been made to reduce the harmful plaque formation and also the risk of infection by adding a biocidal active substance. The biocidic agent is a polymeric condensation product formed from a guanidine derivative and an oxyalkylene diamine. Such polymeric guanidine derivatives are e.g. from WO 01/85676 A1, AT 406 163 B and WO 06/047800.
Es hat sich allerdings gezeigt, dass der biozide Wirkstoff aus dem Dentalwerkstoff mit der Zeit herausgewaschen werden kann, wodurch die Plaque-Bildung wieder begünstigt wird.However, it has been found that the biocidal active substance can be washed out of the dental material over time, whereby the plaque formation is favored again.
Hier setzt nun die vorliegende Erfindung an und stellt sich die Aufgabe, einen polymeren Dentalwerkstoff zur Verfügung zu stellen, welcher den oben genannten Nachteil nicht aufweist.This is where the present invention is based and has as its object the provision of a polymeric dental material which does not have the above-mentioned disadvantage.
Diese Aufgabe wird erfindungsgemäß mit einem polymeren Dentalwerkstoff gelöst, der einen silikatischen Füllstoff enthält, der mit einem polymeren Guanidinderivat auf Basis eines Alkylendiamins und/oder eines Oxyalkylendiamins modifiziert ist. Die Erfindung beruht auf der überraschenden Beobachtung, dass diese polymeren Guanidinderivate so stark an Silikate binden, dass sie praktisch nicht mehr wasserlöslich sind, aus dem Dental werkstoff nicht mehr herausgewaschen werden können, trotzdem aber noch die mikrobiozide Wirkung aufweisen.This object is achieved according to the invention with a polymeric dental material containing a siliceous filler which is modified with a polymeric guanidine derivative based on an alkylenediamine and / or an oxyalkylenediamine. The invention is based on the surprising observation that these polymeric guanidine derivatives bind so strongly to silicates that they are practically no longer soluble in water, from the dental material can not be washed out, but still have the microbiocidal effect.
Silikatische Füllstoffe für Polymere sind an sich bekannt. Wenn nun diese Füllstoffe mit dem polymeren Guanidinderivat modifiziert und in das Polymer eingebracht werden, verleihen sie dem Polymer die Plaque-hemmende Eigenschaft, obwohl sie fest an den silikatischen Füllstoff gebunden sind.Silastic fillers for polymers are known per se. Now, when these fillers are modified with the polymeric guanidine derivative and incorporated into the polymer, they impart the plaque-inhibiting property to the polymer, although they are tightly bound to the siliceous filler.
Eine bevorzugte Ausführungsform des erfmdungsgemäßen polymeren Dentalwerkstoffs ist dadurch gekennzeichnet, dass ein polymeres Guanidinderivat vorgesehen ist, welches das Alkylendiamin und das Oxyalkylendiamin im Molverhältnis zwischen 4:1 und 1:4 enthält. Die Aminogruppen des Alkylendiamins und/oder des Oxyalkylendiamins sind bevorzugt endständig, wobei zur Herstellung des polymeren Guanidinderivates als Alkylendiamin in erster Linie eine Verbindung der allgemeinen FormelA preferred embodiment of the polymeric dental material according to the invention is characterized in that a polymeric guanidine derivative is provided which contains the alkylenediamine and the oxyalkylenediamine in a molar ratio of between 4: 1 and 1: 4. The amino groups of the alkylenediamine and / or the oxyalkylenediamine are preferably terminal, wherein for the preparation of the polymeric guanidine derivative as the alkylenediamine in the first place, a compound of the general formula
NH2(CH2)„NH2 NH 2 (CH 2 ) "NH 2
vorgesehen ist, in welcher n eine ganze Zahl zwischen 2 und 10, insbesondere 6, ist.is provided, in which n is an integer between 2 and 10, in particular 6, is.
Zur Herstellung des polymeren Guanidinderivates kann als Oxyalkylendiamin eine Verbindung der allgemeinen FormelFor the preparation of the polymeric guanidine derivative can as oxyalkylene diamine a compound of the general formula
NH2[(CH2)2O)]n(CH2)2NH2 NH 2 [(CH 2 ) 2 O)] n (CH 2 ) 2 NH 2
vorgesehen werden, in welcher n eine ganze Zahl zwischen 2 und 5, insbesondere 2, ist.be provided, in which n is an integer between 2 and 5, in particular 2.
Insbesondere bevorzugt ist ein polymerer Dentalwerkstoffs, der dadurch gekennzeichnet ist, dass als polymeres Guanidinderivat ein Polyoxyalkylen-Guanidin auf Basis von Triethylenglykoldiamin (relative Molekularmasse: 148), von Polyoxypropylendiamin (relative Molekularmasse: 230) und/oder von Polyoxyethylendiamin (relative Molekularmasse: 600) vorgesehen ist.Particular preference is given to a polymeric dental material which is characterized in that a polyoxyalkylene guanidine based on triethylene glycol diamine (relative molecular mass: 148), of polyoxypropylene diamine (relative molecular mass: 230) and / or of polyoxyethylene diamine (relative molecular mass: 600) is used as the polymeric guanidine derivative. is provided.
Am besten eignet sich ein silikatischer Füllstoff, bei dem als das polymere Guanidinderivat Poly-[2-(2-ethoxy-ethoxyethyl)-guanidinium-hydrochlorid] mit mindestens 3 Guanidinresten vorgesehen ist.Most suitable is a silicate filler in which is provided as the polymeric guanidine derivative poly [2- (2-ethoxyethoxyethyl) guanidinium hydrochloride] having at least 3 guanidine residues.
Das polymere Guanidinderivat besitzt insbesondere eine mittlere Molekularmasse im Bereich von 500 bis 3.000.In particular, the polymeric guanidine derivative has an average molecular weight in the range of 500 to 3,000.
Der Füllstoff kann in einer Menge zwischen 0,05 und 5,0 Gew.-% enthalten sein.The filler may be contained in an amount between 0.05 and 5.0 wt .-%.
Das Polymer ist ein härtbarer Kunststoff, bevorzugt auf Acrylat- oder Methacrylat-Basis.The polymer is a curable plastic, preferably based on acrylate or methacrylate.
Als silikatischer Füllstoff eignet sich nicht nur pulverförmiges SiO2, sondern auch fein verteilte Kieselsäuren und andere Silikate, insbesondere jene, die heute als Füllstoffe in der Kunststofftechnik verwendet werden.As a silicate filler is not only powdery SiO 2 , but also finely divided silicas and other silicates, especially those that are used today as fillers in plastics technology.
Die Bindung des polymeren Guanidinderivates (Wirkstoff) an den silikatischen Füllstoff, also die Trägermatrix, erfolgt durch Vorlage der Matrix, die beispielsweise aus feinen Aerosil- Typen bestehen kann und Einmischen einer 1-30% Gew. -igen wässerigen Lösung des Wirkstoffes bei Raumtemperatur in einem Rührkessel. Das Wasser kann anschließend unter Anwendung herkömmlicher Technologien, wie bespielweise Wirbelschichttrocknern, entfernt werden.The binding of the polymeric guanidine derivative (active ingredient) to the siliceous filler, that is to say the carrier matrix, takes place by presentation of the matrix, which consists, for example, of fine Aerosil Types may exist and mixing a 1-30% Gew. - aqueous solution of the active ingredient at room temperature in a stirred tank. The water can then be removed using conventional technologies, such as fluid bed dryers.
Der in dieser Form matrixgebundene Wirkstoff ist nach wie vor sehr wirksam gegen Mikroorganismen, ist aber so stark an den Füllstoff gebunden, dass er praktisch nicht mehr wasserlöslich ist und herausgewaschen werden kann. Die beschriebene Matrixfixierung des Wirkstoffes verhindert somit die Migration des Wirkstoffes in wässerige Medien. Eine Migration in fetthaltige Medien ist aufgrund der Unlöslichkeit des polaren Wirkstoffes ebenfalls nicht möglich.The matrix-bound active substance in this form is still very effective against microorganisms, but it is so strongly bound to the filler that it is virtually insoluble in water and can be washed out. The described matrix fixation of the active ingredient thus prevents the migration of the active ingredient in aqueous media. Migration into fatty media is also not possible due to the insolubility of the polar agent.
Zur antimikrobiellen Ausrüstung gemäß der Erfindung eignen sich Dentalmaterialien im weiteren Sinn einschließlich im Bereich der Orthodontie oder Kieferchirurgie öder Dentalkosmetik/-ästhetik eingesetzter Materialien. Beispiele sind z.B. Füllungskomposite, K & B -Verblendkunststoffe (für Krone und Brücke), Prothesenkunststoffe, Dentin-Bondings, Abformmaterialien, Abformlöffel, temporäre K&B-Materialien, Implantate, Dental-Geräte, Zahnklammern oder -bänder, Knochenzemente für die Kieferchirurgie und Applikationen dafür.For the antimicrobial equipment according to the invention, dental materials in a broader sense are suitable, including materials used in the field of orthodontics or maxillofacial surgery or dental cosmetics / aesthetics. Examples are e.g. Filling composites, K & B veneering plastics (for crown and bridge), denture resins, dentin bonding, impression materials, impression trays, temporary K & B materials, implants, dental equipment, dental braces or ligaments, bone cements for maxillofacial surgery and applications for it.
Mit den nachfolgenden Beispielen werden bevorzugte Ausführungsformen der Erfindung noch näher beschrieben.The following examples describe preferred embodiments of the invention in more detail.
Beispiel:Example:
Dentalmaterial: ProthesenkunststoffVERSYO.COM von Heraeus Kulzer GmbH, wie in USDental Material: Denture plasticVERSYO.COM from Heraeus Kulzer GmbH, as in US
6,881,360 B2 beschrieben.6,881,360 B2.
A. Herstellung von VERSYO.COM und VERSYO.COM + 0,5% gebundener WirkstoffA. Preparation of VERSYO.COM and VERSYO.COM + 0.5% bound drug
Versyo.com wird aus folgenden Komponenten mit den entsprechenden Gewichtsanteilen hergestellt: a.) Urethandimethacrylat 90,0 b.) Polyesterarethanacrylat 15,0 c.) Oligoethertetraacrylat 13,5 d.) Trimethylopropantrimethacrylat 12,0 e.) Ethoxyliertes Bis-GMA 7,5 ■ f.) Pyrogenes SiO2 10,5 g.) Photoinitiatoren/Stabilisatoren 0,75 h.) Farbpigmente 0,009 Die Komponenten werden homogenisiert und anschließend mit einem geeigneten Lichtgerät polymerisiert.Versyo.com is made from the following components with the appropriate weight fractions: a.) Urethane dimethacrylate 90.0 b.) Polyester arethane acrylate 15.0 c.) Oligoether tetraacrylate 13.5 d.) Trimethylopropane trimethacrylate 12.0 e.) Ethoxylated bis-GMA 7, 5 ■ f.) Pyrogenic SiO 2 10.5 g.) Photoinitiators / stabilizers 0.75 h.) Color pigments 0.009 The components are homogenized and then polymerized with a suitable light device.
Versyo.com + 0,5% gebundener Wirkstoff wird aus folgenden Komponenten mit den entsprechenden Gewichtsanteilen hergestellt: a.) Urethandimethacrylat 90,0 b.) Polyesterurethanacrylat 15,0 c) Oligoethertetraacrylat 13,5 d.) Trimethylopropantrimethacrylat 12,0 e.) Ethoxyliertes Bis-GMA 7,5 f.) Pyrogenes SiO2 9,75 g.) Biozides Guanidinderivat 0,75 h.) Photoinitiatoren/Stabilisatoren 0,75 i.) Farbpigmente 0,009Versyo.com + 0.5% bound active ingredient is prepared from the following components with the appropriate proportions by weight: a.) Urethane dimethacrylate 90.0 b.) Polyester urethane acrylate 15.0 c) oligoether tetraacrylate 13.5 d.) Trimethylopropane trimethacrylate 12.0 e.) Ethoxylated bis-GMA 7.5 f.) Pyrogenic SiO2 9.75 g.) Biocidal guanidine derivative 0.75 h.) Photoinitiators / stabilizers 0.75 i.) Color pigments 0.009
B. Bestimmung der Produkteigenschaften mit/ohne gebundenen Wirkstoff:B. Determination of product properties with / without bound active substance:
Ergebnis: Durch die Zugabe des gebundenen Guanidinderivates werden Produkteigenschaften wie Biegefestigkeit, E-Modul und Viskosität nicht verändert. C. Bestimmung der Zytotoxizität mit/ohne gebundenen Wirkstoff:Result: By adding the bound guanidine derivative, product properties such as flexural strength, modulus of elasticity and viscosity are not changed. C. Determination of cytotoxicity with / without bound drug:
Probenbezeichnung Bewertung gemäß USP25NF Supplement 2 <87> nach 48h nach 72h nach 96hSample designation according to USP25NF Supplement 2 <87> after 48h after 72h after 96h
Versyo.com ohne 0 0 0 ZusatzVersyo.com without 0 0 0 Addition
Versyo.com mit 0 0 0 0,25% WirkstoffVersyo.com with 0 0 0 0.25% active ingredient
Versyo.com mit 0,5% 0 0 0 WirkstoffVersyo.com with 0.5% 0 0 0 active ingredient
Versyo.com mit 0-1 0 0-1 0,75% WirkstoffVersyo.com with 0-1 0 0-1 0.75% active ingredient
Bewertungsschema nach USP 25:Evaluation scheme according to USP 25:
0 keine Zelltoxizität0 no cell toxicity
1 geringe Zelltoxizität, nicht mehr als 20% geschädigte, runde Zellen1 low cell toxicity, no more than 20% damaged, round cells
2 leichte Zelltoxizität, nicht mehr als 50% geschädigte, runde Zellen2 mild cell toxicity, no more than 50% damaged, round cells
3 mäßige Zelltoxizität, nicht mehr als 70% geschädigte, runde Zellen3 moderate cell toxicity, no more than 70% damaged, round cells
4 schwere Zelltoxizität, nalizu vollständige Zellzerstörung4 severe cell toxicity, resulting in complete cell destruction
Ergebnis: Durch die Zugabe von gebundenem Wirkstoff auf Guanidinbasis wird die Zytotoxizität von Versyo.com nicht signifikant erhöht.Result: The addition of Guanidine-based bound drug does not significantly increase Versyo.com's cytotoxicity.
D. Mikrobiologische WirksamkeitD. Microbiological activity
Der erfmdungsgemäß verwendete gebundene Wirkstoff wurde in die Versio.com Acrylatmischung in Anwendungskonzentrationen zwischen 0,25 und 0,75 Gew.-% eingesetzt und anschließend die Wirksamkeit mit den Testkeimen Streptococcus mutans DSM 20523 und Candida albicans DSM 1386 unter Anwendung des Verfahrens JIS Z 2801:2000 an der Kunststoffoberfläche getestet, wobei die Proben bis zu 26 Wochen lang bei 37°C in Reinstwasser unter ständigem Schütteln in einem Verhältnis von 1:1 (cm2xm3) eluiert wurden.The bound active ingredient used according to the invention was used in the Versio.com acrylate mixture in use concentrations between 0.25 and 0.75 wt .-% and then the effectiveness of the test bacteria Streptococcus mutans DSM 20523 and Candida albicans DSM 1386 using the method JIS Z 2801 2000 tested on the plastic surface, the samples were eluted for up to 26 weeks at 37 ° C in ultrapure water with constant shaking in a ratio of 1: 1 (cm 2 xm 3 ).
Die Ergebnisse der bioziden Wirksamkeit sind in Tabelle 1 und 2, die der Migration in Reinstwasser in Tabelle 3 dargestellt.The results of the biocidal efficacy are shown in Tables 1 and 2, those of the migration in ultrapure water in Table 3.
Die Berechnung der Reduktionszahlen (R- Werte) erfolgte nach folgender Formel: The calculation of the reduction numbers (R values) took place according to the following formula:
R: Wert der antimikrobiellen Aktivität, ReduktionszahlR: value of antimicrobial activity, reduction number
A: Lebendkeimzahl an den Teststück direkt nach dem BeimpfenA: live germ count on the test piece immediately after inoculation
B: Lebendkeimzahl am wirkstofffreien Vergleichsmuster nach 24h InkubationB: Live count on the drug-free comparison sample after 24 h incubation
C: Lebendkeimzahl an wirkstoffhältigen Teststück nach 24h InkubationC: Lebendkeimzahl of drug-containing test piece after 24h incubation
Tabelle 1: Antimikrobielle Wirkung auf Streptococcus mutans nach 4 bis 26 Wochen EluationTable 1: Antimicrobial effect on Streptococcus mutans after 4 to 26 weeks of elution
Tabelle 2: Antimikrobielle Wirkung auf Candida albicans nach 2 bis 22 Wochen Eluation Table 2: Antimicrobial effect on Candida albicans after 2 to 22 weeks of elution
Tabelle 3: Eluation - Migration von Füllstoff in Reinstwasser (bei 37°C) Table 3: Eluation - migration of filler in ultrapure water (at 37 ° C)

Claims

Patentansprüche: claims:
1. Polymerer Dentalwerkstoff, dadurch gekennzeichnet, dass er einen silikatischen Füllstoff enthält, der mit einem polymeren Guanidinderivat auf Basis eines Alkylendiamins und/oder eines Oxyalkylendiamins modifiziert ist.1. Polymeric dental material, characterized in that it contains a siliceous filler which is modified with a polymeric guanidine derivative based on an alkylenediamine and / or an oxyalkylenediamine.
2. Polymerer Dentalwerkstoff nach Anspruch 1, dadurch gekennzeichnet, dass ein polymeres Guanidinderivat vorgesehen ist, welches das Alkylendiamin und das Oxyalkylendiamin im Molverhältnis zwischen 4:1 und 1:4 enthält.2. Polymeric dental material according to claim 1, characterized in that a polymeric guanidine derivative is provided which contains the alkylenediamine and the oxyalkylenediamine in a molar ratio between 4: 1 and 1: 4.
3. Polymerer Dentalwerkstoff nach einem der Ansprüche 1 bis oder 2, dadurch gekennzeichnet, daß die Aminogruppen des Alkylendiamins und/oder des Oxyalkylendiamins endständig sind.3. Polymeric dental material according to any one of claims 1 to or 2, characterized in that the amino groups of the alkylenediamine and / or oxyalkylenediamine are terminal.
4. Polymerer Dental Werkstoff nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, daß zur Herstellung des polymeren Guanidinderivates als Alkylendiamin eine Verbindung der allgemeinen Formel4. Polymeric dental material according to one of claims 1 to 3, characterized in that for the preparation of the polymeric guanidine derivative as alkylene diamine a compound of the general formula
NH2(CH2)nNH2 NH 2 (CH 2 ) n NH 2
vorgesehen ist, in welcher n eine ganze Zahl zwischen 2 und 10, insbesondere 6, ist.is provided, in which n is an integer between 2 and 10, in particular 6, is.
5. Polymerer Dentalwerkstoff nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, daß zur Herstellung des polymeren Guanidinderivates als Oxyalkylendiamin eine Verbindung der allgemeinen Formel5. Polymeric dental material according to one of claims 1 to 3, characterized in that for the preparation of the polymeric guanidine derivative as oxyalkylenediamine a compound of the general formula
NH2[(CH2)2O)]n(CH2)2NH2 NH 2 [(CH 2 ) 2 O)] n (CH 2 ) 2 NH 2
vorgesehen ist, in welcher n eine ganze Zahl zwischen 2 und 5, insbesondere 2, ist.is provided, in which n is an integer between 2 and 5, in particular 2.
6. Polymerer Dentalwerkstoff nach einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, dass als polymeres Guanidinderivat ein Polyoxyalkylen-Guanidin auf Basis von Triethylenglykoldiamin (relative Molekularmasse: 148), von Polyoxypropylendiamin (relative Molekularmasse: 230) und/oder von Polyoxyethylendiamin (relative Molekularmasse: 600) vorgesehen ist. 6. Polymeric dental material according to one of claims 1 to 5, characterized in that the polymeric guanidine derivative is a polyoxyalkylene guanidine based on triethylene glycol diamine (relative molecular mass: 148), of polyoxypropylenediamine (relative molecular mass: 230) and / or of polyoxyethylene diamine (relative molecular mass : 600) is provided.
7. Polymerer Dentalwerkstoff nach einem der Ansprüche 1 bis 6, dadurch gekennzeichnet, dass als das polymere Guanidinderivat Poly-[2-(2-ethoxy-ethoxyethyl)- guanidinium-hydrochlorid] mit mindestens 3 Guanidinresten vorgesehen ist.7. Polymeric dental material according to one of claims 1 to 6, characterized in that is provided as the polymeric guanidine derivative poly [2- (2-ethoxy-ethoxyethyl) - guanidinium hydrochloride] with at least 3 guanidine radicals.
8. Polymerer Dentalwerkstoff nach einem der Ansprüche 1 bis 7, dadurch gekennzeichnet, dass die mittlere Molekularmasse des polymeren Guanidinderivates im Bereich 500 bis 3.000 liegt.8. Polymeric dental material according to one of claims 1 to 7, characterized in that the average molecular weight of the polymeric guanidine derivative is in the range 500 to 3,000.
9. Polymerer Dentalwerkstoff nach einem der Ansprüche 1 bis 8 auf Acrylat- oder Methacrylat-Basis.9. Polymeric dental material according to one of claims 1 to 8 based on acrylate or methacrylate.
10. Polymerer Dentalwerkstoff nach Anspruch 9, dadurch gekennzeichnet, dass der Füllstoff in einer Menge zwischen 0,05 und 5,0 Gew.-% enthalten ist.10. Polymeric dental material according to claim 9, characterized in that the filler is contained in an amount between 0.05 and 5.0 wt .-%.
11. Verwendung eines polymeren Dentalwerkstoffes zur Herstellung von Materialien für die Orthodontie, Kieferchirurgie und Dentalkosmetik/-ästhetik, insbesondere Füllungskomposite, K & B -Verblendkunststoffe für Kronen und Brücken, Prothesenkunststoffe, Dentin- Bondings, Abformmaterialien, Abformlöffel, temporäre K&B-Materialien, Implantate, Dental-Geräte, Zahnklammern oder -bänder, Knochenzemente für die Kieferchirurgie und Applikationen dafür. 11. Use of a polymeric dental material for the production of materials for orthodontics, maxillofacial surgery and dental cosmetics / aesthetics, in particular filling composites, K & B veneering resins for crowns and bridges, denture plastics, dentine bonding, impression materials, impression trays, temporary K & B materials, implants , Dental devices, dental braces or straps, bone cements for oral surgery and applications therefor.
EP08772586A 2007-07-16 2008-07-16 Dental material Withdrawn EP2180870A2 (en)

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AT0111707A AT505563B1 (en) 2007-07-16 2007-07-16 DENTAL MATERIAL
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DE102009052725A1 (en) * 2009-11-12 2011-05-19 B. Braun Melsungen Ag Use of polyoxyalkylenediamine-based polyguanidine derivatives for medical articles
DE102009052721A1 (en) 2009-11-12 2011-05-26 B. Braun Melsungen Ag Use of polymeric or oligomeric active ingredients for medical articles
AR079639A1 (en) 2009-12-17 2012-02-08 Colgate Palmolive Co COMPOSITION OF ANTI-EROSIVE TOOTHPASTE
BR112012017707B1 (en) 2010-01-29 2021-11-09 Colgate-Palmolive Company COMPOSITION FOR ORAL HYGIENE FOR CARE OF SENSITIVE ENAMEL
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WO2017182536A1 (en) 2016-04-20 2017-10-26 Ineos Styrolution Group Gmbh Antimicrobially active, non-leaching thermoplastic molding compounds
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