WO1981001959A1 - Method for the preparation of dental protheses by photopolymerization of a plastic mass - Google Patents

Method for the preparation of dental protheses by photopolymerization of a plastic mass Download PDF

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Publication number
WO1981001959A1
WO1981001959A1 PCT/DE1981/000014 DE8100014W WO8101959A1 WO 1981001959 A1 WO1981001959 A1 WO 1981001959A1 DE 8100014 W DE8100014 W DE 8100014W WO 8101959 A1 WO8101959 A1 WO 8101959A1
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WO
WIPO (PCT)
Prior art keywords
mass
dental
bicyclo
color
exposure
Prior art date
Application number
PCT/DE1981/000014
Other languages
German (de)
English (en)
French (fr)
Inventor
P Jochum
O Gasser
Original Assignee
Espe Pharm Praep
P Jochum
O Gasser
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 Espe Pharm Praep, P Jochum, O Gasser filed Critical Espe Pharm Praep
Priority to DE8181900218T priority Critical patent/DE3162715D1/de
Priority to AT81900218T priority patent/ATE6736T1/de
Priority to JP50212781A priority patent/JPS58500900A/ja
Publication of WO1981001959A1 publication Critical patent/WO1981001959A1/de

Links

Classifications

    • 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

Definitions

  • polymerizable materials based on ethylenically unsaturated compounds are used to a large extent to produce the various dental prostheses, such as full crowns, veneering of metal crowns and the visible part of dental bridge constructions.
  • the plastic dental prosthetic items thus produced are preferred to the ceramic materials in many cases because of their lower price, easier processing and lower brittleness, especially since the ceramic dental prosthetic items also have a much higher hardness than the natural ones. Have tooth substance and therefore the respective counter bite is at risk of wear when used.
  • methyl methacrylate and di- or polyfunctional acrylic acid esters or methacrylic acid esters are mostly used as ethylenically unsaturated compounds, with the aim of reducing the shrinkage of the polymerization and increasing the mechanical strength as well as matching the color of the natural teeth, the monomers before the polymerization Fillers, dyes, fluorescent agents and the like can be added.
  • fillers are u. a. pre-pigmented polymethacrylate beads or other powdered organic polymers as well as inorganic fillers, in particular microfine fillers, such as fumed silica.
  • the polymerization and curing of the monomer preparations can in principle be carried out by adding the usual free radical formers as polymerization catalysts. Because of the high demands on color stability, only the polymerization in the heat using peroxides, e.g. Proven lauroyl or benzoyl peroxide. Due to the limited shelf life of the prepared mixture of monomer, fillers and auxiliary materials as well as the peroxides, these materials are usually made available to the dental technician as two-component systems. Here, one of the components consists of a peroxide-free monomer preparation and the other of a monomer-free peroxide preparation. The two components are then mixed immediately before processing.
  • peroxides e.g. Proven lauroyl or benzoyl peroxide.
  • the photoinitiators such as benzoin alkyl ethers or benzil monoketals, which respond to UV light, in particular with a wavelength of 320 to 400 nm, have inadequate color stability, particularly in the very light colorations required in crown and bridge materials, and lead in particular to the darker colorations required in some cases Monomer preparations only for insufficient hardening inside the molded articles produced therefrom.
  • the irradiation with UV light requires technically complex and therefore expensive lamps which have a relatively short lifespan.
  • DE-OS 29 14 537 describes such mixtures for the preparation of tooth crowns, benzil and benzoin alkyl ether being used as photoinitiators.
  • peroxides are additionally added to the polymerizable compositions.
  • this measure again decisively affects the shelf life of this preparation.
  • Better curing depths can be achieved with the 1,2-diketone compounds which respond to the short-wave portion of visible light at wavelengths of approx. 400 - 600 nm as photoinitiators, especially if they are used together with amines, such as in DE-OS 22 51 048 has been disclosed.
  • the object of the invention is therefore to provide a method for producing crowns and bridge constructions or the like dental prosthetic items made of plastics, which meets all requirements, in particular with regard to the color stability and coloring possibility of the dental prosthetic items and excludes the disadvantages and possible errors of the known two-component systems.
  • the strength properties of the plastic material are not reduced here, because only the initiator compounds are degraded during the post-exposure. Since the bleaching of these particular bicyclodiketones also occurs in the presence of light-stable pigments, the use of the method according to the invention makes it possible to produce colored dental prostheses which do not change their color even for years to come.
  • esters of acrylic and methacrylic acid have proven particularly useful as ethylenically unsaturated polymerizable monomers in the photopolymerizable compositions.
  • the (meth) acrylic esters of di- or polyfunctional alcohols as described, for example, in DE-OS 28 16 823 or DE-PS 19 21 869, are preferably used alone or in a mixture with other multifunctional or monofunctional (meth) acrylates used.
  • the known organic or inorganic fillers or mixtures thereof can be used.
  • Prepigmented polymethacrylate beads are preferred as organic fillers, while inorganic fillers are suitable Quartz or silicate glasses in finely ground form or mineral fillers such as calcium fluoride can be used. Particularly good results are obtained by using microfine fillers, such as pyrogenic silica, alone or together.
  • the constituents mentioned are also used in the usual amounts in the process according to the invention.
  • the fillers used can also be silanized in a known manner in order to improve the bond with the polymer.
  • a silane e.g. Trimethoxy- (3-methacryloxy-propy1) -silane used.
  • inhibitors such as e.g. p-Methoxyphenol can be added in the usual concentrations.
  • the color stability of the polymers under the influence of sunlight can be improved by adding known UV stabilizers. These stabilizers should no longer absorb to any appreciable extent above a wavelength of approx. 350 nm in order not to impair the light-curing process; suitable e.g. 2-hydroxy-4-methoxybenzophenone or ethyl 2-cyano-3,3-diphenyl acrylate.
  • bicyclo- [2.2.1] - heptanedione-2,3-initiators to be used according to the invention are used in amounts of 0.01% by weight to 1% by weight, preferably in a concentration of 0.05% by weight to 0.5 % By weight, in particular 0.1-0.3%, were added to the dental materials.
  • Examples of such bicyclo- [2.2.1] - heptanedione-2,3-compounds are norcampherquinone (bicyclo [2.2.1] -heptanedione-2,3), camphorquinone (1,7,7-trimethyl-bicyclo - [2.2.1] - heptanedione-2,3) and the tricyclo
  • camphorquinone has proven itself in the process according to the invention, which, together with the activating amine compounds, preferably causes rapid polymerization when the monomers are exposed in the dental materials and then relatively quickly after the polymerization by means of others Exposure can be bleached out.
  • Particularly suitable amine components are tertiary amines, which preferably carry substituted carbon hydrogen radicals. Tertiary amines with three hydroxy-substituted hydrocarbon groups, such as triethanolamine or its derivatives, are particularly preferred. The amines are added to the composition in concentrations of 0.1% by weight to 10% by weight, preferably 0.5% by weight to 5% by weight.
  • the diketone and optionally the amine are dissolved in the monomer and mixed with the other components in a simple manner, e.g. by stirring or kneading, and processed to a spreadable mass. Care must be taken to prevent light from entering the photosensitive dental material during manufacture and storage. By stirring with evacuation or processing with a roller mill or similar measures, a homogeneous, bubble-free material is produced and filled into opaque containers.
  • the tooth replacement part is preferably produced in a similar manner to the method according to DE-AS 15 16 456, in which the semi-liquid or plastic monomer mass is applied in layers to a base, each layer being cured by heat treatment before the next layer is applied.
  • a layer of the monomer composition of the desired coloring is applied to the bridge framework or a model tooth stump a suitable instrument, e.g. a brush or a spatula.
  • a denture part can be modeled that meets high cosmetic requirements.
  • an intense, visible light-emitting light source e.g. 75-watt halogen projector lamp
  • the exposure time for each layer is between 1 second and 20 seconds, in most cases approx. 5 seconds is sufficient.
  • the fully modeled dental prosthesis part is then optionally exposed to further irradiation while cooling, preferably to the light of a lamp which has a high output in the
  • the postexposure can also be carried out under vacuum; the post-exposure is preferably carried out at a pressure of ⁇ 10 mbar.
  • the bleaching ability through the aftertreatment is a special feature of the bicyclo- [2.2.1] -heptanedione-2,3-compounds used in the process according to the invention Series of 1, 2-diketone initiators for photopolymerization. This is clear from the results of the series of tests described below.
  • camphorquinone completely colorless according to the invention b) phenanthrenequinone canary yellow c) benzil strongly yellow c) ⁇ -naphthil strongly red e) P, P'-dichlorobenzene yellow f) acenaphtenquinone strongly red g) P, P'-dimethoxybenzil yellow h) diacetyl slightly yellow volatile, very unpleasant smell i) 3, 4-hexanedione slightly yellow very unpleasant smell j) 1, 2-cyclohexanedione no polymerization k) Furil strongly yellow l) 2-Naphtil strongly yellow m) p-Nitrobenzil no polymerization n) 4,4-Dimethylbenzil yellow
  • the photoinitiator system consisting of the specific bicycloheptanedione compounds and preferably an amine makes it possible for dental technicians to be provided with one-component systems which are resistant to dark storage and which have other advantages besides the color stability.
  • the plastic mass is applied to a metal base (e.g. made of gold or platinum alloy) by heating during the polymerization and subsequent cooling because of the different thermal expansion coefficients of metal and plastic, stresses and gaps at the connection point, which increase the strength reduce the number of dentures. Since the photopolymerization proceeds with a comparatively small increase in temperature, these phenomena hardly occur. In addition, incorrect dosing, inhomogeneous mixtures, as well as air pockets and similar mixing errors are avoided. Also, no residual quantities have to be discarded, so that the material according to the invention is very economical to use.
  • a powder mix is produced from
  • the liquid is placed in a laboratory kneader and the powder mixture is slowly added. After a kneading time of about 1 h, the mass obtained is further homogenized on a roller mill and then kneaded again under vacuum until a bubble-free, spreadable product is obtained which has a certain thixotropy. If the mass is colored lightly, as is required for the cutting area of tooth replacement parts (corresponding to the color Sll of the "Biodent" color ring from the company De Trey), it hardens after 20 seconds of exposure to the light of a commercially available, visible light-emitting lamp dental use (Elipar device, company ESPE) in a layer thickness of 8 mm.
  • a commercially available, visible light-emitting lamp dental use (Elipar device, company ESPE) in a layer thickness of 8 mm.
  • the compressive strength of the polymer is measured on test specimens of 2 x 2 x 4 mm, which are produced in suitable forms by primary exposure (20 sec.) Using the dental exposure device mentioned above.
  • the initially clearly yellow bodies are 60 min. exposed to light from a light source that emits the wavelength range between 400 and 500 nm with high intensity.
  • the moldings now obtained, which have the pure color of the selected coloring, have a compressive strength of 410 MPa after 24 hours of storage under water at 36 ° C.
  • Example 1 a crown and bridge material is produced which contains tricyclo [5.2.1.0 2,6 ] -decanedione-8,9 as the photoinitiator instead of camphorquinone, produced in a known manner by oxidation of the tricyclo [5.2.1.0 2.6 ] d-ecan-8-ons is colored with selenium dioxide and in a light toothbrush color (corresponding to the color Sll of the "Biodent" color ring from De Trey). The resulting material cures on exposure as described in Example 1 in a layer thickness of 7 mm (Elipar lamp, from ESPE). A cylindrical test specimen of 15 mm in diameter and 1.5 mm in thickness is produced in a suitable plastic mold by a primary exposure of 40 seconds. After a secondary exposure time of 1 hour under the light of a lamp that emits a high intensity in the range between 400 and 500 nm, the initially colored test specimen shows the pure color of the selected color.
  • Example 1 a crown and bridge material is produced which contains bicyclo- [2.2.1] -heptan-dione-2,3 (norcampherquinone) as the photoinitiator instead of camphor quinone and in a light tooth-cutting color (corresponding to the color Sll of the "Biodenf - Color ring by De Trey) is colored.
  • a test specimen produced as in Example 2 is initially colored yellow and, after the corresponding secondary exposure (1 hour), has the pure color of the chosen coloring.
  • Example 2 In the same way as in Example 1, a crown and bridge material is produced, in the preparation of which 360 mg of triethanolamine-tris-phenylurethane are added as an activator. The mass is colored in a dark brown, which is required for the production of the tooth necks for tooth replacement parts (corresponding to the color H32 of the "Biodenf color ring from De Trey).
  • Example 5 After 20 seconds of exposure, the material cures in a layer thickness of 4 mm. Its compressive strength is 430 MPa (measured as in Example 1).
  • Example 5
  • Example 4 materials are produced in the desired colors for the tooth neck, dentin and tooth cutting edge.
  • Example 4 The materials manufactured according to Example 4 are provided in the desired colors. The required colors are applied in layers to the bridge framework, which is provided with the usual retentions and coated with opaque. Each layer is polymerized by exposure as described in Example 5. The material behind the metal retentions also hardens.
  • Example 5 the bleaching is again carried out by post-exposure, possibly with a change of position of the bridge, in order to expose all parts to the light.
  • the veneers obtained in this way are notable for their color and abrasion resistance. In addition, their appearance is completely flawless cosmetically.

Landscapes

  • Health & Medical Sciences (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Plastic & Reconstructive 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)
  • Dental Prosthetics (AREA)
PCT/DE1981/000014 1980-01-17 1981-01-15 Method for the preparation of dental protheses by photopolymerization of a plastic mass WO1981001959A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
DE8181900218T DE3162715D1 (en) 1980-01-17 1981-01-15 Method for the preparation of dental protheses by photopolymerization of a plastic mass
AT81900218T ATE6736T1 (de) 1980-01-17 1981-01-15 Verfahren zur herstellung von zahnersatzteilen durch photopolymerisieren einer verformbaren masse.
JP50212781A JPS58500900A (ja) 1981-01-15 1981-06-12 プラスチツク被覆した糸格子の補強材およびその製造装置

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19803001616 DE3001616A1 (de) 1980-01-17 1980-01-17 Verfahren zur herstellung von zahnersatzteilen durch photopolymerisieren einer verformbaren masse
DE3001616 1980-01-17

Publications (1)

Publication Number Publication Date
WO1981001959A1 true WO1981001959A1 (en) 1981-07-23

Family

ID=6092315

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/DE1981/000014 WO1981001959A1 (en) 1980-01-17 1981-01-15 Method for the preparation of dental protheses by photopolymerization of a plastic mass

Country Status (5)

Country Link
US (1) US4351853A (en, 2012)
EP (1) EP0043825B1 (en, 2012)
JP (1) JPH0229647B2 (en, 2012)
DE (2) DE3001616A1 (en, 2012)
WO (1) WO1981001959A1 (en, 2012)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0150422A3 (en) * 1983-12-30 1986-06-04 Espe Fabrik Pharmazeutischer Praparate Gmbh Process for preparing gypsum models for dentistry
EP0374824A3 (de) * 1988-12-19 1991-04-17 THERA Patent GmbH & Co. KG Gesellschaft für industrielle Schutzrechte Dentalmassen, die bifunktionelle Acrylsäure- oder Methacrylsäureester enthalten
US5583164A (en) * 1988-12-19 1996-12-10 Espe Stiftung & Co. Produktions-Und Vertriebs Kg Dental compositions comprising bifunctional or polyfunctional acrylic-acid esters or methacrylic-acid esters
WO2022012915A1 (de) * 2020-07-16 2022-01-20 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e. V. Photopolymerisierbare zusammensetzung für die additive fertigung

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DE3136484A1 (de) * 1981-09-15 1983-03-31 Kulzer & Co Gmbh, 6380 Bad Homburg "verfahren zur photopolymerisation von vinylverbindu ngen und photopolymerisierbares material"
IE54502B1 (en) * 1982-03-04 1989-10-25 Ici Plc Photopolymerisable compositions
DE3240907A1 (de) * 1982-11-05 1984-05-10 ESPE Fabrik pharmazeutischer Präparate GmbH, 8031 Seefeld Verfahren zur herstellung individueller gussteile
DE3316591C1 (de) * 1983-05-06 1990-05-31 Dieter 8581 Goldkronach Wunderlich Verfahren zur Herstellung von mit einem Verblendkunststoff überzogenen zahntechnischen Metallgerüsten
US4863977A (en) * 1983-11-16 1989-09-05 Dentsply Research & Development Corp. Process for preparing interpenetrating polymer network objects employing rubber-modified polymers
US5210109A (en) * 1983-11-16 1993-05-11 Dentsply Research & Development Corp. Interpenetrating polymer network compositions employing rubber-modified polymers
US4551486A (en) * 1983-11-16 1985-11-05 Dentsply Research & Development Corp. Interpenetrating polymer network compositions
US4711913A (en) * 1983-11-16 1987-12-08 Dentsply International Inc. Interpenetrating polymer network compositions employing rubber-modified polymers
US4604295A (en) * 1983-12-22 1986-08-05 Loctite Corporation Visible light absorbing peroxy-esters
DE3510611A1 (de) * 1985-03-23 1986-09-25 Bayer Ag, 5090 Leverkusen Beschichtungsmaterial fuer kollagenhaltige materialien
US4892478A (en) * 1988-03-21 1990-01-09 Dentsply Research & Development Corp. Method of preparing dental appliances
DE3837569A1 (de) * 1988-11-04 1990-05-10 Espe Stiftung Mit sichtbarem licht aushaertbare dentalmassen
ATE114241T1 (de) * 1990-11-17 1994-12-15 Heraeus Kulzer Gmbh Polymerisierbares dentalmaterial.
DE4110612C2 (de) * 1990-11-17 1995-10-19 Heraeus Kulzer Gmbh Polymerisierbares Dentalmaterial
US5833464A (en) * 1996-07-26 1998-11-10 Ivoclar A.G. Method for manufacturing a ceramic dental replacement
US6282013B1 (en) 1997-04-30 2001-08-28 Lasermed, Inc. System for curing polymeric materials, such as those used in dentistry, and for tailoring the post-cure properties of polymeric materials through the use of light source power modulation
AU1198199A (en) 1997-10-29 1999-05-17 Bisco, Inc. Dental composite light curing system
US6200134B1 (en) 1998-01-20 2001-03-13 Kerr Corporation Apparatus and method for curing materials with radiation
US6204302B1 (en) 1998-11-20 2001-03-20 Bisco, Inc. Photosensitizers for free radical polymerization initiation resins and method of making the same
SE530196C2 (sv) * 2004-09-30 2008-03-25 Nobel Biocare Ab Förfarande och anordning för att åstadkomma färgsättning eller nyansering av protetik samt sådan protetik
US20140134572A1 (en) * 2005-12-15 2014-05-15 Coltene Ag Polymeric Material for Taking a Dental Impression and Method Thereof
US9072572B2 (en) 2009-04-02 2015-07-07 Kerr Corporation Dental light device
US9066777B2 (en) * 2009-04-02 2015-06-30 Kerr Corporation Curing light device
DE102012001978A1 (de) * 2012-02-02 2013-08-08 Voco Gmbh Dentale Kompositmaterialien enthaltend tricyclische Weichmacher
JP2020529873A (ja) * 2017-02-22 2020-10-15 インター—メッド インク 倍音特徴を利用した歯科材料の加熱、染料の吸収、および材料特性
JP7153736B2 (ja) * 2018-09-26 2022-10-14 株式会社ジーシー 歯科用組成物

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DE1516456B1 (de) * 1966-03-14 1970-04-30 Williams Gold Refining Co Verfahren zur Herstellung von Zahnersatzteilen aus Kunststoff
FR2156760A1 (en, 2012) * 1971-10-18 1973-06-01 Ici Ltd
US3756827A (en) * 1972-01-25 1973-09-04 Du Pont L compounds and selected sensitizerss photopolymerizable compositions containing cyclic cis-alpha-dicarbony
DE2419887A1 (de) * 1973-04-24 1974-11-21 Ici Ltd Dentalmassen
EP0002831A2 (de) * 1978-01-03 1979-07-11 ESPE Fabrik Pharmazeutischer Präparate GmbH Opakes, photopolymerisierbares Zahnfüllmaterial

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FR893477A (fr) * 1942-04-20 1944-07-28 Reichsverband Deutscher Dentis Procédé de fabrication d'appareils de prothèse, en particulier de prothèse dentaire
GB1465897A (en) 1973-04-24 1977-03-02 Ici Ltd Dental compositions
US4024297A (en) * 1976-02-02 1977-05-17 Ppg Industries, Inc. Actinic light polymerizable coating compositions
JPS55102A (en) * 1978-03-15 1980-01-05 Sankin Ind Co Preparation of false tooth floor by photoohardening and photoohardening material
US4131729A (en) * 1978-04-21 1978-12-26 Espe Fabrik Pharmazeutischer Praparate Gmbh Dental compositions comprising acrylic esters of tricyclo [5.2.1.02,6 ] decane polymers

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1516456B1 (de) * 1966-03-14 1970-04-30 Williams Gold Refining Co Verfahren zur Herstellung von Zahnersatzteilen aus Kunststoff
FR2156760A1 (en, 2012) * 1971-10-18 1973-06-01 Ici Ltd
US3756827A (en) * 1972-01-25 1973-09-04 Du Pont L compounds and selected sensitizerss photopolymerizable compositions containing cyclic cis-alpha-dicarbony
DE2419887A1 (de) * 1973-04-24 1974-11-21 Ici Ltd Dentalmassen
EP0002831A2 (de) * 1978-01-03 1979-07-11 ESPE Fabrik Pharmazeutischer Präparate GmbH Opakes, photopolymerisierbares Zahnfüllmaterial

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0150422A3 (en) * 1983-12-30 1986-06-04 Espe Fabrik Pharmazeutischer Praparate Gmbh Process for preparing gypsum models for dentistry
EP0374824A3 (de) * 1988-12-19 1991-04-17 THERA Patent GmbH & Co. KG Gesellschaft für industrielle Schutzrechte Dentalmassen, die bifunktionelle Acrylsäure- oder Methacrylsäureester enthalten
US5583164A (en) * 1988-12-19 1996-12-10 Espe Stiftung & Co. Produktions-Und Vertriebs Kg Dental compositions comprising bifunctional or polyfunctional acrylic-acid esters or methacrylic-acid esters
WO2022012915A1 (de) * 2020-07-16 2022-01-20 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e. V. Photopolymerisierbare zusammensetzung für die additive fertigung

Also Published As

Publication number Publication date
EP0043825A1 (de) 1982-01-20
JPS56501869A (en, 2012) 1981-12-24
EP0043825B1 (de) 1984-03-21
US4351853A (en) 1982-09-28
JPH0229647B2 (en, 2012) 1990-07-02
DE3001616A1 (de) 1981-07-23
DE3162715D1 (en) 1984-04-26

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