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WO1986003120A1 - Composition a base de silicone pour la preparation de moulages dentaires - Google Patents

Composition a base de silicone pour la preparation de moulages dentaires Download PDF

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Publication number
WO1986003120A1
WO1986003120A1 PCT/US1985/002280 US8502280W WO8603120A1 WO 1986003120 A1 WO1986003120 A1 WO 1986003120A1 US 8502280 W US8502280 W US 8502280W WO 8603120 A1 WO8603120 A1 WO 8603120A1
Authority
WO
WIPO (PCT)
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.)
Ceased
Application number
PCT/US1985/002280
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English (en)
Inventor
Toshiko Makiyama
Bernd Martin 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 WO1986003120A1 publication Critical patent/WO1986003120A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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 .

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (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

Compositions à base de silicone indiquées pour des moulages dentaires, durcissables par une réaction de polycondensation catalysée par un composé d'étain II. L'amélioration consiste à utiliser un catalyseur d'étain stabilisé par une amine, ce qui permet d'obtenir une composition présentant une longue durée de conservation avant l'utilisation/le durcissement. Cette composition remplace avantageusement les compositions de l'art antérieur, durcies par polyaddition, produisant des articles d'un meilleur fini et de surface uniforme. Sont également décrits un procédé de préparation de la composition et le durcissement permettant d'obtenir les articles façonnés.
PCT/US1985/002280 1984-11-22 1985-11-21 Composition a base de silicone pour la preparation de moulages dentaires Ceased WO1986003120A1 (fr)

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
BRPI8405939 1984-11-22

Publications (1)

Publication Number Publication Date
WO1986003120A1 true WO1986003120A1 (fr) 1986-06-05

Family

ID=4036831

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1985/002280 Ceased WO1986003120A1 (fr) 1984-11-22 1985-11-21 Composition a base de silicone pour la preparation de moulages dentaires

Country Status (3)

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

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0787766A1 (fr) * 1996-02-01 1997-08-06 Wacker-Chemie GmbH Caoutchouqes de silicone vulcanisant à température ambiante et réticulables par un mécanisme de condensation
EP0748621A3 (fr) * 1995-06-16 2000-03-08 GE Bayer Silicones GmbH & Co. KG Nouvelles compositions de catalyseurs/réticulants, leur procédé de préparation et utilisation
EP1228745A1 (fr) * 2001-02-05 2002-08-07 Heraeus Kulzer GmbH & Co.KG Utilisation d'un matériau silicone libre d'oxides de polyalkyléne et/ou des dérivés d'oxides de polyalkyléne comme empreinte
US20160136058A1 (en) * 2013-07-10 2016-05-19 Coltène/Whaledent Ag System for filling a root canal of a tooth and for covering pulp

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB841825A (en) * 1955-08-05 1960-07-20 Wacker Chemie Gmbh Process for the manufacture of elastomeric organo-polysiloxane products
US3950300A (en) * 1972-10-11 1976-04-13 Wacker-Chemie Gmbh Dental impression materials
FR2366334A1 (fr) * 1976-09-30 1978-04-28 Bayer Ag Composition pateuse pour la reticulation d'organopolysiloxanes en caoutchoucs de silicone
GB2026000A (en) * 1978-06-30 1980-01-30 G C Dental Ind Corp Dental silicone compositions and the method of using the same

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB841825A (en) * 1955-08-05 1960-07-20 Wacker Chemie Gmbh Process for the manufacture of elastomeric organo-polysiloxane products
US3950300A (en) * 1972-10-11 1976-04-13 Wacker-Chemie Gmbh Dental impression materials
FR2366334A1 (fr) * 1976-09-30 1978-04-28 Bayer Ag Composition pateuse pour la reticulation d'organopolysiloxanes en caoutchoucs de silicone
GB2026000A (en) * 1978-06-30 1980-01-30 G C Dental Ind Corp Dental silicone compositions and the method of using the same

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0748621A3 (fr) * 1995-06-16 2000-03-08 GE Bayer Silicones GmbH & Co. KG Nouvelles compositions de catalyseurs/réticulants, leur procédé de préparation et utilisation
EP0787766A1 (fr) * 1996-02-01 1997-08-06 Wacker-Chemie GmbH Caoutchouqes de silicone vulcanisant à température ambiante et réticulables par un mécanisme de condensation
US6172150B1 (en) 1996-02-01 2001-01-09 Wacker-Chemie Gmbh Room-temperature vulcanizing condensation-crosslinking silicone rubbers
EP1228745A1 (fr) * 2001-02-05 2002-08-07 Heraeus Kulzer GmbH & Co.KG Utilisation d'un matériau silicone libre d'oxides de polyalkyléne et/ou des dérivés d'oxides de polyalkyléne comme empreinte
US20160136058A1 (en) * 2013-07-10 2016-05-19 Coltène/Whaledent Ag System for filling a root canal of a tooth and for covering pulp

Also Published As

Publication number Publication date
BR8405939A (pt) 1986-06-17
EP0203149A1 (fr) 1986-12-03

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