EP0203149A1 - Silikonzusammensetzung zur herstellung von zahnabdruckmassen - Google Patents

Silikonzusammensetzung zur herstellung von zahnabdruckmassen

Info

Publication number
EP0203149A1
EP0203149A1 EP85906013A EP85906013A EP0203149A1 EP 0203149 A1 EP0203149 A1 EP 0203149A1 EP 85906013 A EP85906013 A EP 85906013A EP 85906013 A EP85906013 A EP 85906013A EP 0203149 A1 EP0203149 A1 EP 0203149A1
Authority
EP
European Patent Office
Prior art keywords
composition
catalyst
general formula
cst
tin
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Withdrawn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
EP85906013A
Other languages
English (en)
French (fr)
Inventor
Toshiko Makiyama
Bernd Martin Estrada de Servidao S/No. REIDL
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.)
Union Carbide Corp
Original Assignee
Union Carbide Corp
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 Union Carbide Corp filed Critical Union Carbide Corp
Publication of EP0203149A1 publication Critical patent/EP0203149A1/de
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • 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 dental composition based on polysiloxane, which rapidly cures by a condensation reaction at ambient temperature, comprising:
  • R, alkyl, and, optionally
  • filler material for the formation of a desired composition
  • talc paraffin
  • pyrogenic silica -2- calciu carbonate
  • quartz quartz
  • water starch and pigments.
  • the present invention relates to a hydroxysilicone composition with a combination of cross-linking agent/ catalyst which polymerizes through a condensation reaction, and is useful for the accurate molding of teeth.
  • This two- component system comprises two pastes, or a paste and a low-viscosity liquid which, after being mixed, vulcanize at ambient temperature, i.e., the paste of the first component containing hydroxysilane polymerizes after being mixed with the cross-linking agent/catalyst within 2-5 minutes at ambient temperature to provide an elastomeric article.
  • Si li cone compositions for dental impressions are well known and widely used.
  • they comprise dime hy lpolysiloxane with vinyl terminal groups, a catalyst based in platinum compounds and filler material, and are available at various consistencies, from non-fluid pastes to fluids.
  • the second member also consists of pastes or fluids comprising si lane terminal groups or internal silane functionality for cross-linking and elastomer formation.
  • the disadvantage of dental impressions obtained by polyaddition reactions and based on vinyl-si licone is the -3- re lease o ' f hydrogen gas which, after the introduction of the filler material in the composition, causes imperfections on the surface of the finished article.
  • the hydrogen gas is formed by reaction of the vinyl groups of dimethylpolysiloxane with the non- reacted Si-H groups of the cross-linking agent, since they are in excess, and the hydrogen gas formation is brought about by the mouth moisture, by the subsequent application of plaster and by the platinum catalyst.
  • the damaged surface of plaster has a large number of small craters, thus impairing the quality of the finished article.
  • German "Of fenlegunsschrif t" No. 2926405 describes a process to avoid these disadvantages.
  • palladium or palladium alloys of high commercial value are incorporated to the system, using the known hydrogen absorption by palladium.
  • compositions consist of two pastes, or a paste and a fluid, i.e., one base paste comprising hydroxyl silicone fluid with filler material and a cross-linking agent/catalyst paste or fluid containing tetraal yloxide silane with organic tin compounds as catalysts.
  • U. S. patents 4,360,354 and 4,1-37,249 describe the use of tin IV compounds as active catalysts for the promotion of condensation of the hydroxi-terminated dimethylpolysiloxane fluid.
  • Diorganopolysiloxanes capped with hydroxyl terminal groups may be cross-linked by a mixture containing a reaction product of esters of silicic acids with or-ganic tin IV compounds of the general formula
  • R is an alkyl radical and R' is a monovalent hydrocarbon radical.
  • These cross-linking agents/catalysts are based on well known stable tin IV compounds. Catalyst materials for the condensation of hydroxypolysiloxanes , and tetraalkyloxide si lanes based on tin II compounds are less known. The oxi dative instability of the tin II compounds with chemical structure such as
  • R* is a monovalent hydrocarbon radical
  • -5- Repeated exposure to air and moisture of the catalytic compounds of tin II causes a chemical decomposition into substances which no longer catalyse, nor cause polycondensa- tion of polysiloxanes containing hydroxyl groups.
  • the simple combination of tin II compounds with tetraalkyloxisilanes also inactivates the cat_alyst, even without exposure to air and or humidity.
  • tin II compounds such as tin bis (2-ethylhexoate)
  • tertiary amines such as tris-isooctyl amine and formulated with tetraalkyloxide silanes
  • the tin II compound becomes unexpectedly stable to oxidative decomposition by addition of small quantities of te tiary amines.
  • the stability deficiency of the tin II active catalyst was overcome in a simple manner, using a stabilizing agent for tin II, such as tertiary amines in general and, more specifically, longer chain alkyl tertiary amines, and preferably, tris-isooctyl- amine together with di- , tri- and tetraalkyloxide silanes and, most preferably, tetraethoxysilane.
  • a stabilizing agent for tin II such as tertiary amines in general and, more specifically, longer chain alkyl tertiary amines, and preferably, tris-isooctyl- amine together with di- , tri- and tetraalkyloxide silanes and, most preferably, tetraethoxysilane.
  • this invention relates, in particular, to dental compositions based on polysiloxanes curable at ambient temperature and cross-linkable by poly condensation reaction, containing:
  • R methoxy, ethoxy, propoxy, butoxy
  • R monovalent hydrocarbon, and stabilized from oxidative decomposition by a primary, secondary or tertiary amine of the general formula
  • hydroxysilicone compositions according to this invention are useful for the production of dental molds , such molds accurately reproducing tooth details through dental plaster molds.
  • the preparation of the mold consists of a thorough mixing of the base component with the cross-linking agent/ catalyst component, subsequent introduction of this mixture into the oral cavity, where solidification occurs, and the removal of the cured mold from the oral cavity.
  • the dental model is then obtained by filling the mold with plaster which, after curing, accurately reproduces the teeth forms.
  • compositions are:
  • the silicone fluid (a) is a dimethylpolysiloxane with hydroxyl terminal groups or internal hydroxyl functionality, with viscosity between 50 cst to several million cst, at 25°C, depending on the desired consistency of the composition.
  • the filler (b) may be quartz, calcium carbonate, metal silicates, precipitated or pyrogenic silica, talc, , vaseline or paraffin, starches or similar.
  • the cross- linking agent (c) is a di- , tri- or tetra- alkyloxisilane , particularly polydimethylsiloxane, which has alkyloxide functionality on at least two silicon atoms per molecule.
  • Ethyl orto-and/or polysilicates are particularly useful.
  • the ethyl polysilicates may have a Si0 2 content of up to 40%.
  • Siloxane copolymers of various molecular weights and trialkyloxisilyl or dialkyloxisyl terminal groups are well known.
  • the catalyst (d) is a tin II compound prepared from tin bis (2-ethylhexoate) stabilized with tertiary amine such as tri-isooctylamine. This stabilized tin II catalyst was unknown up to the present time.
  • the stabilized catalyst may be used in a fluid condition or formulated with inert fillers to produce a paste.
  • Colorants and pigments are used for differentiation between the base paste and the catalyst and as a control of the mixture uniformity. Inorganic and organic pigments are preferred. ⁇
  • the base paste was prepared by mixing 19% polydimethyl- siloxane with hydroxyl terminal groups, with a viscosity of 20000 cst at 25°C; 16.6% micronized talc; 7.6% calcium carbonate; 2% pyrogenic silica with a specific surface of
  • the cross-linking agent/catalyst was prepared mixing 45% ethyl polysilicate with a 35% SiO- content, 45% tin bis (2-ethylhexoate) , and 10% tri-isooctylamine.
  • the cross-linking agent/catalyst was put into a closed glass bottle and placed in an oven, kept at a constant temperature of 45°C+2°C, during 8 months. After this period of time, the procedure of this example was repeated, only modified by the fact that the cross-linking agent/catalyst aged in the oven was used and the evolution of the Shore A hardness did not change significantly.
  • the base paste was prepared as described in example 1.
  • a cross-linking agent/catalyst paste was prepared mixing 39.6 parts of 35% ethyl polysilicate, 39.6 parts of tin bis (ethylhexoate) , and 8.8 parts tri-isooctylamine and 10.6% of hydrophobic pyrogenic silica, and 1.4 of an inorganic pigment.
  • the cross- linking agent/catalyst fluid was prepared mixing 50 parts of ethyl polysi licate with 35% SiO- content , with 50 parts of tin bis ( 2-ethylhexoate ) , with no amine stabili zing agent .
  • the cross-linking agent/catalys t fluid thus prepared was placed in a closed glass bottle and kept at ambient temperature during one month .
  • the base paste was prepared according to examp le 1 , and 17 grams of the base paste were mixed with 15 drops of the cross-linking agent/catalyst fluid aged at ambient temperature , as s tated in this example .
  • the mixture was applied to a dental molding frame and introduced into the oral cavity of a person . Fi fteen minutes -11- after the introduction into the oral cavity there was no sign of siginificant hardening of the mixture.
  • the only difference in relation to procedure 1 was the lack of tri-isooctylamine as stabilizer of the cross-linking agent/ catalyst system.
  • this invention refers essentially to a composition for dental molds that cross- links by poly- condensation reaction at ambient temperature, the composi ⁇ tion comprising:
  • a cross-linking agent consisting of di- , tri- or tetra-alkyloxysiloxane or organopolysiloxane with at least two alkyloxide groups per molecule, most preferably ethyl orto-and/or polysilicate;
  • a catalyst to accelerate the condensation reaction consisting of a tin II compound, preferably tin bis(2-ethyl- hexoate) stabilized with a primary, secondary or tertiary amine, preferably a tertiary amine with long aliphatic chain and, most preferably, tri-isooctylamine;
  • hydrophobic pyrogenic or precipitated silica (e) hydrophobic pyrogenic or precipitated silica, paraffin wax, calcium carbonate, quartz, water, corn starch and pigments or other known filler materials ,or carriers.
  • the paste obtained in ( 2) above or (d) may be combined with the paste obtained in ( 1) above for the forma ⁇ tion of a mixture that cross-links (hardens ) within 2 to 5 minutes , forming a useful elastomer for dental impressions .

Landscapes

  • Health & Medical Sciences (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Dental Preparations (AREA)
EP85906013A 1984-11-22 1985-11-21 Silikonzusammensetzung zur herstellung von zahnabdruckmassen Withdrawn EP0203149A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
BR8405939A BR8405939A (pt) 1984-11-22 1984-11-22 Composicao de silicone para moldagens dentarias,curavel por condensacao,processo para formacao da composicao,processo para formacao de um artigo de moldagem e artigo elastomerico formado da composicao
BR8405939 1984-11-22

Publications (1)

Publication Number Publication Date
EP0203149A1 true EP0203149A1 (de) 1986-12-03

Family

ID=4036831

Family Applications (1)

Application Number Title Priority Date Filing Date
EP85906013A Withdrawn EP0203149A1 (de) 1984-11-22 1985-11-21 Silikonzusammensetzung zur herstellung von zahnabdruckmassen

Country Status (3)

Country Link
EP (1) EP0203149A1 (de)
BR (1) BR8405939A (de)
WO (1) WO1986003120A1 (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0748621B1 (de) * 1995-06-16 2003-09-03 GE Bayer Silicones GmbH & Co. KG Neue Katalysator/Vernetzer-Kompositionen, ein Verfahren zu deren Herstellung und deren Verwendung
DE19603628A1 (de) * 1996-02-01 1997-08-07 Wacker Chemie Gmbh Bei Raumtemperatur vulkanisierende, kondensationsvernetzende Siliconkautschuke
DE10105357A1 (de) * 2001-02-05 2002-08-29 Heraeus Kulzer Gmbh & Co Kg Verwendung einer polyalkylenpolyoxidfreien und/oder polyalkylenoxidderivatfreien, bei Raumtemperatur durch Kondensation aushärtenden Silikonmasse
EP2823800B1 (de) * 2013-07-10 2019-08-21 Coltène/Whaledent AG System zur Füllung eines Zahnwurzelkanals und zur Überdeckung von Pulpa

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3127363A (en) * 1955-08-05 1964-03-31 Process for the manufacture of elasto-
US3950300A (en) * 1972-10-11 1976-04-13 Wacker-Chemie Gmbh Dental impression materials
DE2644193C2 (de) * 1976-09-30 1987-03-12 Bayer Ag, 5090 Leverkusen Vernetzer und Härtungskatalysatoren enthaltende pastöse Massen als Komponente für bei Raumtemperatur vulkanisierbare Polysiloxanelastomere
JPS591241B2 (ja) * 1978-06-30 1984-01-11 而至歯科工業株式会社 歯科用シリコ−ン組成物およびその使用法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO8603120A1 *

Also Published As

Publication number Publication date
WO1986003120A1 (en) 1986-06-05
BR8405939A (pt) 1986-06-17

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Inventor name: REIDL, BERND, MARTINESTRADA DE SERVIDAO, S/NO.

Inventor name: MAKIYAMA, TOSHIKO