WO1993017654A1 - Dental impression materials containing quadri-functional siloxane polymers - Google Patents

Dental impression materials containing quadri-functional siloxane polymers Download PDF

Info

Publication number
WO1993017654A1
WO1993017654A1 PCT/US1993/001930 US9301930W WO9317654A1 WO 1993017654 A1 WO1993017654 A1 WO 1993017654A1 US 9301930 W US9301930 W US 9301930W WO 9317654 A1 WO9317654 A1 WO 9317654A1
Authority
WO
Grant status
Application
Patent type
Prior art keywords
weight
dental impression
impression material
viscosity
percent
Prior art date
Application number
PCT/US1993/001930
Other languages
French (fr)
Inventor
Vincent Paradiso
Original Assignee
Vincent Paradiso
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

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K6/00Preparations for dentistry
    • A61K6/10Compositions for taking dental impressions

Abstract

Dental impression materials have improved tear strength and resist tearing upon removal from a set of teeth, especially form a dramatically undercut set of teeth. The dental impression materials incorporate a mono- and quadri-functional (MQ) siloxane component into a silicone-based dental impression material composition. A method of taking a dental impression uses the modified materials.

Description

DENTAL IMPRESSION MATERIALS CONTAINING QUADRI- FUNCTIONAL SILOXANE POLYMERS

BACKGROUND OF THE INVENTION

The present invention is based upon the discovery that dental impression materials can be produced which have increased tear strength by adding a mono- and quadri-functional siloxane polymer to the material prior to taking a dental impression.

The use of siloxane polymers in dental impression materials has been taught in the prior art. U.S. Patent Nos. 4,657,959 and 4,752,633 disclose dental impression materials which contain silicone polymers having mono- and di-functional silicon atoms. U.S. Patent No. 4,877,854 discloses many polyorganosiloxane polymers useful as dental impression materials. These dental impression materials have suffered from a low tear strength causing problems when removing the molding materials from a set of teeth, particularly teeth having severe undercuts.

The silicone polymers which have been used are based upon linear siloxane chains having functional end groups which enable cross-linking at the chain ends.

Little or no cross-linking takes place along the length of the chains.

In order to improved the tear strength of these prior impression materials, various fillers have been added, particularly hydrophobic fillers.

U.S. Patent No. 4,359,565 discloses the use of a diatomaceous earth filler in combination with a polydimethyl siloxane silicone polymer. The polydimethyl siloxanes disclosed container either vinyl end groups or dimethylhydridosilyl end groups. It is known that when impressions are made with siloxane materials, the final product has to date exhibited poor tear strength.

Vinylsiloxane systems have been used for impression materials since they are odorless, tasteless and dimensionally stable. Unfortunately, currently available vinylsiloxane impression materials also exhibit poor tear strength.

A need exists for a vinylsiloxane dental impression material having improved tear strength and a resistance to tearing upon removal from a set of teeth.

SUMMARY OF THE INVENTION;

The present invention overcomes the problems encountered by the prior art dental impression materials by providing a dental impression material having improved tear strength and a resistance to tearing upon removal from a set of teeth, especially from a dramatically undercut set of teeth. The present invention provides a dental impression material having improved tear strength and resistance by incorporating a mono- and quadri-functional (MQ) siloxane component into a silicone-based dental impression material composition. The dental impression materials of the present invention comprise:

(A) about 25% to about 90% by weight vinyl end-stopped linear siloxane polymer having a viscosity of from about 100 to about 1,500,000 cps at 25°C, or blends of such polymers;

(B) a siloxane resin containing mono- and quadri-functional silicon atoms, referred to as an MQ resin, present in an amount of up to about 75 percent by weight such that the total of Components (A) and (B) is from about 15% to about 90% of the total weight of the dental impression material;

(C) up to about 85% by weight at least one filler selected from the group consisting of silica, cornstarch, quartz, quartz flours, calcium silicate, calcium carbonate, calcium sulfate, pumice flours. crystoballite flours, hydrated alumina, diatomaceous earth, talc and precipitated and pyrogenically produced silicon dioxide;

(D) from about 1 percent to about 10 percent by weight methyl hydrogen polysiloxane cross-linking agent having a viscosity of less than about 500 cps at 25°C;

(E) platinum containing catalyst present in an amount of up to about 6% by weight; and

(F) up to about 4% by weight coloring agent. By incorporating an MQ component in accordance with the present invention, a dental impression material is provided which can cure quickly in a patient's mouth and form a strong and lasting impression of an intraoral structure which remains intact after removal.

DETAILED DESCRIPTION OF THE INVENTION;

The tear strength of a silicone composition can be increased by adding an MQ component to the composition. It is believed that the quadri-functionality of the MQ resins enables a great deal of cross-linking within a silicone composition. In strictly linear silicone polymers which react only at their end groups, very little cross-linking along the chain takes place. With an MQ polymer, however, a matrix of cross-links is provided which adds to the strength and durability of an entire composition.

The present invention relates to incorporating an MQ-containing siloxane component into a silicone polymer system, and using the system to take a dental impression of an intraoral structure. An intraoral structure is defined herein as a set of teeth, a single tooth, a set of dentures, a set of gums, a prosthetic device, or the like. The materials of the present invention may also be used as bite registration materials. A bite registration is also herein considered to be included as an impression of an intraoral structure.

According to a preferred embodiment of the present invention, the dental impression material comprises a siloxane composition having;

(A) about 25% to about 90% by weight vinyl end-stopped linear siloxane polymer having a viscosity of from about 100 to about 1,500,000 cps at 25ºC, or blends of such polymers;

(B) a siloxane resin containing mono- and quadri-functional silicon atoms, present in an amount of up to about 75 percent by weight such that the total of Components (A) and (B) is from about 15% to about 90% of the total weight of the siloxane composition;

(C) up to about 85% by weight at least one filler selected from the group consisting of silica, cornstarch, quartz, diatomaceous earth, talc and silica gel;

(D) from about 1 percent to about 10 percent by weight methyl hydrogen polysiloxane cross-linking agent having a viscosity of less than about 500 cps at 25ºC;

(E) platinum containing catalyst present in an amount of up to about 6% by weight; and

(F) up to about 4% by weight coloring agent.

Component (A) can generally be described as a siloxane polymer having functional end-stops. In a preferred embodiment, component (A) comprises a vinyl-dimethyl terminated polydimethylsiloxane. Other polyorganosiloxanes may also be used.

Depending upon what type of dental impression material is desired, the chain length of Component (A) may vary such that a wide variety of viscosities may be employed. For a mono-phasic material from which a final dental impression is taken in a single step, a low to medium viscosity impression material is desired. A medium viscosity or "medium body" impression material typically includes a polyorganosiloxane polymer for Component (A) which has a viscosity of from about 100 to about 100,000 cps at 25°C. Typical polymers which are readily available on the market include those having viscosities of 100, 200, 1,000, 2,000, 10,000, 60,000, 65,000 and 165,000 cps at 25°C. Any of these may be used for Component (A) of a medium body dental impression material.

Many of the medium body materials may be prepared and applied from a tray or from a syringe. To facilitate application of the heavier viscosity materials, such as those containing a 1,000 to 165,000 cps siloxane polymer for Component (A), preparation and application from a tray is preferred.

Thicker viscosity materials are called "tray weight" or "heavy body" materials and typically contain a polyorganosiloxane for Component (A) which has a viscosity of from about 1,000 to about 165,000 cps at 25°C. A viscosity of from about 10,000 to about 100,000 is preferred for component (A) in a heavy body material. Tray weight or heavy body materials are generally not preferred for taking a one-step impression since they provide much less detail than is usually desired.

Tray weight or heavy body materials are commonly used for two-step impression methods. According to a two-step method, a heavy body is used to take a preliminary impression of a tooth, set of teeth, or any portion of dentition. The impression material around the preparation is then relieved (slightly enlarged), e.g. by carving, and filled with a much lighter weight material as described below. The two-layer impression material is then reapplied to the dentition so as to form a two-layer impression having even greater detail around the preparation.

Putties may also be used for two-step impressions and are preferred in some cases. A putty-weight material may comprise a polyorganosiloxane for Component (A) having a viscosity of from about 100 to about 1,500,000 cps at 25ºC. The heavier viscosity polymers are preferably used for Component (A) when formulating a putty-weight material. A putty-weight impression material generally has a much higher filler content than any of the lighter weight materials.

Lighter viscosity compositions are used during the second step of a two-step impression process. These compositions provide the highest detail of the dental impression materials due to their fluidity. These lightweight materials are generally called "syringe weight" and contain very little filler. Syringe weight materials typically contain a polyorganosiloxane for Component (A) which has a viscosity of about 100 to about 65,000 cps at 25ºC. Syringe weight materials containing Component (A) having a viscosity of up to 65,000 cps at 25°C may be used but are not preferred. According to some preferred embodiments, the syringe weight material comprises Component (A) having a viscosity of 100 to 10,000 cps at 25°C.

The viscosity of any of the different weight compositions can be controlled by varying the viscosity of the silicone oil, the ratio of silicone oil to filler, the affinity of the filler for the silicone oil (oil absorption number) and the density and specific surface area of the filler.

As can be seen, the amounts and viscosities of Component (A) may vary depending upon the desired application of the dental impression material. In general, the lower viscosity of the polymer used, the higher the durometer of the cured material. Dental materials containing two or more polymers having different viscosities from each other may also be employed for Component (A).

The improved tear strength and tear resistance of the dental impression materials of the present invention can be attributed to the incorporation of Component (B), a siloxane resin containing mono- and quadri-functional silicon atoms. These silicon atoms are considered mono- and quadri-functional based on the degree of functionality of methylsilicon or other organic substituent subunits. When clusters of quadri-functional silicon atoms are very small, almost all of the silicons are on the outer surface and thus have unattached SiOH groups sticking out. When these SiOH groups are capped off with Me3Si - or M units, an MQ resin results.

At the lower molecular weight end of MQ resins are tetrakis(trimethylsiloxy)silane, (Me3SiO) or M4Q, and tris(trimethylsiloxy)silanol, (Me3SiO)3SiOH or M3QOH. At the upper end of the weight range are gels. The most useful materials are those with a molecular weight range of from about 1,000 to about 10,000. A broader range of materials may also be used, for instance, materials in the molecular weight range of about 100 to about 100,00. The range of MW in the product, or polydispersity, is usually broad and somewhat dependent upon the method of preparation.

Based upon the total weight of the impression material. Component (B) may be present in an amount of up to about 75 parts by weight. Preferably, Component (B) is present in an amount of from about 1 to about 25 percent by weight, more preferably from about 5 to about 15 percent by weight. In a particularly preferred embodiment. Component (B) is present from about 5 to about 7 percent by weight. Component (B) preferably has a viscosity of from about 4,000 to about 6,000 cps at 25°C.

The combination of Components (A) and (B) should make up from about 15 to about 90 percent by weight of the total impression material formulation.

Component (C) is a filler which may be added to the dental impression material in an appropriate amount depending upon the viscosity desired. As discussed above with respect to Component (A), very little filler is added to provide a syringe weight material whereas a large amount of filler is added to provide a putty-weight material. Generally, the filler is added in amounts of up to about 85 percent by weight based upon the total weight of the material. For a syringe weight material, between about 5 and about 35 percent by weight Component (C) are added. For a putty-weight material, about 55 to about 85 percent by weight Component (C) is added. The amount of filler and the viscosity of Component (A) may be varied within their appropriate ranges to provide the various weight dental impression materials discussed herein.

The filler is generally selected from silica, silica gel, cornstarch, quartz, quartz flours, calcium silicate, calcium carbonate, calcium sulfate, pumice flours, crystoballite flours, hydrated alumina, diatomaceous earth, talc and precipitated and pyrogenically produced silicon dioxide and other fillers known to those of ordinary skill in the art. High surface area fillers, e.g. 100 m2/gm and higher, are preferred. One specific filler which may be used is in many of the compositions is Aerosil™ available from Degussa Company, Richfield Park, New Jersey.

Component (D) comprises a cross-linker containing hydride substituents off of a polysiloxane chain. Preferred cross-linkers include methyl hydrogen polysiloxanes, preferably linear methyl hydrogen polysiloxanes. The cross-linking agent preferably has a viscosity of less than about 250 cps at 25°C and more preferably from about 25 to about 75 cps at 25°C. Preferably, up to about 50 percent of the substituents off of the siloxane chain are hydride substituents.

Component (D) is preferably present in an amount of between 1 and about 10 percent by weight depending upon the viscosity and the desired degree of cross-linking. Greater amounts of cross-linker are employed with formulations for harder impression materials, e.g. bite registration materials. More preferably, from about 3 to about 8 percent by weight Component (D) is employed. In one embodiment, when about 3 to about 8 percent by weight Component (D) is employed, the cross-linker has a viscosity of about 40 centipoise at 25ºC.

Component (E) is a platinum catalyst used to catalyze the cross-linking of the siloxane components within the dental material. In a preferred embodiment. Component (E) is a vinyl-dimethyl terminated polydimethylsiloxane platinum complex. When mixed with the cross-linking agent and reactive polymers and fillers, the platinum catalyst allows the composition to cure relatively quickly such that the dental impression material does not need to remain within a patient's mouth for any extended period of time.

Since the platinum catalyst in the presence of cross-linker and reactive polymer and/or filler allows the composition to cure so quickly, it is separated from the cross-linking agent such that the dental impression material comprises two individual phases which are mixed just prior to use. The one phase contains the platinum catalyst while the other phase contains the cross-linking agent. Preferably, Components (A) and (C) are divided among the two phases such that the viscosities of the two phases are substantially similar. Component (B) is added to a first phase which contains the cross-linker whereas the platinum catalyst is incorporated into the second phase.

Component (E) is preferably present in an amount of up to about 6 percent by weight depending upon the available vinyl reactive units in components (A) and (B). The more vinyl present in the uncured material, the more catalyst and cross-linker necessary. In a preferred embodiment, the platinum catalyst is added such that approximately 20 ppm of platinum is available in the material. The platinum catalyst is preferably a platinum complex containing vinyl-dimethyl terminated polydimethylsiloxane and platinum supplied from a platinum tetrachloride salt.

Component (F) is a coloring agent which facilitates inspection of the detail provided by the impression material. The coloring agent is preferably present in an amount of up to about 4 percent by weight, about 0.2 to about 4 percent being a more preferred range. Typical coloring agents used for Component (F) include FDC colors and iron oxides.

In order to substantially equalize the viscosities between the two phases, usually more filler is added to the phase containing the cross-linking agent than to the phase containing the platinum catalyst. This is especially useful when the cross-linking agent has a low viscosity e.g., about 40 centipoise at 25°C. The increased amount of filler in the phase containing the low viscosity cross-linking agent tends to increase the viscosity of the phase. It is preferred to have substantially equal viscosities between the two phases in order to facilitate miscibility when mixed just prior to being applied on a patient's teeth. Most preferably, the two phases have identical viscosities.

Preferably, the two phases of a syringe weight material each have a viscosity in the range of from about 1 to about 125,000 cps at 25ºC. For medium and heavy weight materials, the viscosities for each phase are preferably from about 75,000 to about 250,000 and about 200,000 to about 800,000 cps at 25°C, respectively. Putty weight materials preferably have viscosities in the range of from about 750,000 to about 1,500,000 cps at 25°C. Of course, it is preferred that the two phases of any weight material have similar, if not almost identical, viscosities.

Although the present invention has been described in connection with preferred embodiments, it will be appreciated by those skilled in the art that additions, modifications, substitutions and deletions not specifically described may be made without departing from the spirit and scope of the invention defined in the appended claims.

Claims

WHAT IS CLAIMED IS:
1. A dental impression material comprising a first siloxane composition molded into an impression of an intraoral structure, said first siloxane composition comprising:
(A) about 25% to about 90% by weight vinyl end-stopped linear siloxane polymer having a viscosity of from about 100 to about 1,500,000 cps at 25°C, or blends of such polymers;
(B) a siloxane resin containing mono- and quadri-functional silicon atoms and having a molecular weight of from about 100 to about 100,000, said resin present in an amount of up to about 75 percent by weight such that the total of Components (A) and (B) is from about 15% to about 90% of the total weight of the dental impression material;
(C) up to about 85% by weight at least one filler selected from the group consisting of silica, cornstarch, quartz, quartz flours, calcium silicate, calcium carbonate, calcium sulfate, pumice flours, crystoballite flours, hydrated alumina, diatomaceous earth, talc and precipitated and pyrogenically produced silicon dioxide;
(D) from about 1 percent to about 10 percent by weight methyl hydrogen polysiloxane cross-linking agent having a viscosity of less than about 500 cps at 25°C;
(E) platinum containing catalyst present in an amount of up to about 6% by weight; and
(F) up to about 4% by weight coloring agent. 2. A dental impression material as defined in claim 1, wherein Component (B) is present in an amount of between about 1 and about 25 percent by weight.
3. A dental impression material as defined in claim 1, wherein Component (B) is present in an amount of between about 5 and about 15 percent by weight. 4. A dental impression material as defined in claim 1, wherein Component (B) is present in an amount of between about 5 and about 7 percent by weight. 5. A dental impression material as defined in claim 1, wherein Component (A) has a viscosity of between about 100 and about 1,000 cps at 25°C. 6. A dental impression material as defined in claim 1, wherein Component (A) has a viscosity of between about 1,000 and about 10,000 cps at 25ºC. 7. A dental impression material as defined in claim 1, wherein Component (A) has a viscosity of between about 10,000 and about 100,000 cps at 25°C. 8. A dental impression material as defined in claim 1, wherein Component (A) has a viscosity of between about 100,000 and about 1,500,000 cps at 25ºC. 9. A dental impression material as defined in claim 1, wherein Component (A) is a vinyl-dimethyl terminated polydimethylsiloxane. 10. A dental impression material as defined in claim 1, wherein Component (E) is a vinyl-dimethyl terminated polydimethylsiloxane platinum complex. 11. A dental impression material as defined in claim 1, wherein Component (F) is at least one FDC color.
12. A dental impression material as defined in claim 1, wherein Component (F) is at least one iron oxide material. 13. A dental impression material as defined in claim 1, further comprising a second siloxane composition having:
(A) about 25% to about 90% by weight vinyl end-stopped linear siloxane polymer having a viscosity of from about 100 to about 1,500,000 cps at 25°C, or blends of such polymers;
(B) a siloxane resin containing mono- and quadri-functional silicon atoms and having a molecular weight of from about 100 to about 100,000, said resin present in an amount of up to about 75 percent by weight such that the total of Components (A) and (B) is from about 15% to about 90% of the total weight of the dental impression material;
(C) up to about 85% by weight at least one filler selected from the group consisting of silica, cornstarch, quartz, quartz flours, calcium silicate, calcium carbonate, calcium sulfate, pumice flours, crystoballite flours, hydrated alumina, diatomaceous earth, talc and precipitated and pyrogenically produced silicon dioxide;
(D) from about 1 percent to about 10 percent by weight methyl hydrogen polysiloxane cross-linking agent having a viscosity of less than about 500 cps at 25ºC;
(E) platinum containing catalyst present in an amount of up to about 6% by weight; and
(F) up to about 4% by weight coloring agent, wherein said second siloxane composition is a coating on top of said first siloxane composition and wherein said second siloxane composition has a viscosity which is less than a viscosity of the first siloxane composition. 14. A method of taking a dental impression comprising:
applying a first dental impression material to an intraoral structure;
allowing said first dental impression material to substantially cure so as to maintain the impression of said intraoral structure when removed therefrom; and removing said first dental impression material from said intraoral structure to form a dental impression, wherein said first dental impression material comprises:
(A) about 25% to about 90% by weight vinyl end-stopped linear siloxane polymer having a viscosity of from about 100 to about 1,500,000 cps at 25°C, or blends of such polymers;
(B) a siloxane resin containing mono- and quadri-functional silicon atoms and having a molecular weight of from about 100 to about 100,000, said resin present in an amount of up to about 75 percent by weight such that the total of Components (A) and (B) is from about 15% to about 90% of the total weight of the dental impression material;
(C) up to about 85% by weight at least one filler selected from the group consisting of silica, cornstarch, quartz, quartz flours, calcium silicate, calcium carbonate, calcium sulfate, pumice flours, crystoballite flours, hydrated alumina, diatomaceous earth, talc and precipitated and pyrogenically produced silicon dioxide;
(D) from about 1 percent to about 10 percent by weight methyl hydrogen polysiloxane cross-linking agent having a viscosity of less than about 500 cps at 25°C; (E) platinum containing catalyst present in an amount of up to about 6% by weight; and
(F) up to about 4% by weight coloring agent. 15» A method as defined in claim 14, wherein said first dental impression material comprises a two-part system, said two-part system comprising;
part (I) Component (B), Component (D), a portion of Component (A) and a portion of Component (C); and part (II) comprises Component (E), and the remaining portions of Components (A) and (C), wherein said method includes the step of mixing parts (I) and (II) to form said first dental impression material prior to applying said first dental impression material to said intraoral structure. 16. A method as defined in claim 14, wherein said method further includes the step of applying a second dental impression material to said dental impression to from a two-layer dental impression material, said second dental impression material comprising:
(A) about 25% to about 90% by weight vinyl end-stopped linear siloxane polymer having a viscosity of from about 100 to about 1,500,000 cps at 25°C, or blends of such polymers;
(B) a siloxane resin containing mono- and quadri-functional silicon atoms and having a molecular weight of from about 100 to about 100,000, said resin present in an amount of up to about 75 percent by weight such that the total of Components (A) and (B) is from about 15% to about 90% of the total weight of the dental impression material;
(C) up to about 85% by weight at least one filler selected from the group consisting of silica, cornstarch, quartz, quartz flours, calcium silicate, calcium carbonate, calcium sulfate, pumice flours, crystoballite flours, hydrated alumina, diatomaceous earth, talc and precipitated and pyrogenically produced silicon dioxide;
(D) from about 1 percent to about 10 percent by weight methyl hydrogen polysiloxane cross-linking agent having a viscosity of less than about 500 cps at 25°C;
(E) platinum containing catalyst present in an amount of up to about 6% by weight; and
(F) up to about 4% by weight coloring agent, said second dental impression material having a viscosity which is less than a viscosity of said first dental impression material;
applying the two-layer dental impression material to said intraoral structure;
allowing said second dental impression material of said two-layer dental impression material to substantially cure so as to maintain the intraoral impression when removed from the oral cavity; and
removing said two-layer dental impression material from said intraoral structure to form a two-layer dental impression.
AMENDED CLAIMS
[received by the International Bureau on 20 July 1993 (20.07.93);
original claims 1,13 and 14 amended;
remaining claims unchanged (5 pages)] 1. A dental impression material comprising a first siloxane composition, said dental impression material being molded into an impression of an intraoral structure, said first siloxane composition comprising the reaction product of:
(A) about 25% to about 90% by weight vinyl end- stopped linear siloxane polymer having a viscosity of from about 100 to about 1,500,000 cps at 25°C, or blends of such polymers;
(B) up to about 75% by weight siloxane resin containing mono- and quadri-functional silicon atoms and having a molecular weight of from about 100 to about 100,000, said resin present in an amount effective to increase the tear strength of said dental impression material, wherein the total of Components (A) and (B) is from about 15% to about 90% of the total weight of the dental impression material, said siloxane resin increasing the tear strength of the impression material by providing a matrix of cross-links enabled by the quadri-functionality of the resin, wherein the matrix of cross-links adds to the strength and durability of the entire composition;
(C) up to about 85% by weight at least one filler selected from the group consisting of silica, cornstarch, quartz, quartz flours, calcium silicate, calcium carbonate, calcium sulfate, pumice flours, cristobalite flours, hydrated alumina, diatomaceous earth and talc;
(D) from about 1 percent to about 10 percent by weight methyl hydrogen polysiloxane cross-linking agent having a viscosity of less than about 500 cps at 25ºC;
(E) a catalytic amount of platinum containing catalyst; and
(F) up to about 4% by weight coloring agent.
2. A dental impression material as defined in claim 1, wherein Component (B) is present in an amount of between about 1 and about 25 percent by weight.
12. A dental impression material as defined in claim 1, wherein Component (F) is at least one iron oxide material. 13. A dental impression material as defined in claim 1, further comprising a second siloxane composition comprising the reaction product of:
(A1) about 25% to about 90% by weight vinyl end-stopped linear siloxane polymer having a viscosity of from about 100 to about 1,500,000 cps at 25°C, or blends of such polymers;
(B1) up to about 75% by weight siloxane resin containing mono- and quadri-functional silicon atoms and having a molecular weight of from about 100 to about 100,000, said resin present in an amount effective to increase the tear strength of said dental impression material, wherein the total of Components (A1) and (B1) is from about 15% to about 90% of the total weight of the dental impression material, said siloxane resin increasing the tear strength of the impression material by providing a matrix of cross- links enabled by the quadri-functionality of the resin, wherein the matrix of cross-links adds to the strength and durability of the entire composition;
(C1) up to about 85% by weight at least one filler selected from the group consisting of silica, cornstarch, quartz, quartz flours, calcium silicate, calcium carbonate, calcium sulfate, pumice flours, cristobalite flours, hydrated alumina, diatomaceous earth and talc;
(D1) from about 1 percent to about 10 percent by weight methyl hydrogen polysiloxane cross-linking agent having a viscosity of less than about 500 cps at 25ºC;
(F1) a catalytic amount of a platinum containing catalyst; and (F1) up to about 4% by weight coloring agent, wherein said second siloxane composition is a coating on top of said first siloxane composition and wherein said second siloxane composition has a
viscosity which is less than the viscosity of the first siloxane composition. 14. A method of taking a dental impression comprising:
applying a first dental impression material to an intraoral structure;
allowing said first dental impression material to substantially cure so as to maintain the impression of said intraoral structure when removed therefrom; and removing said first dental impression material from said intraoral structure to form a dental impression, wherein said first dental impression material comprises:
(A) about 25% to about 90% by weight vinyl end- stopped linear siloxane polymer having a viscosity of from about 100 to about 1,500,000 cps at 25°C, or blends of such polymers;
(B) a siloxane resin containing mono- and quadri- functional silicon atoms and having a molecular weight of from about 100 to about 100,000, said resin present in an amount of up to about 75 percent by weight such that the total of Components (A) and (B) is from about 15% to about 90% of the total weight of the dental impression material;
(C) up to about 85% by weight at least one filler selected from the group consisting of silica, cornstarch, quartz, quartz flours, calcium silicate, calcium carbonate, calcium sulfate, pumice flours, cristobalite flours, hydrated alumina, diatomaceous earth, talc and precipitated and pyrogenically produced silicon dioxide;
(D) from about 1 percent to about 10 percent by weight methyl hydrogen polysiloxane cross-linking agent having a viscosity of less than about 500 cps at 25ºC;
PCT/US1993/001930 1992-03-02 1993-03-02 Dental impression materials containing quadri-functional siloxane polymers WO1993017654A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US84478792 true 1992-03-02 1992-03-02
US844,787 1992-03-02

Publications (1)

Publication Number Publication Date
WO1993017654A1 true true WO1993017654A1 (en) 1993-09-16

Family

ID=25293632

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1993/001930 WO1993017654A1 (en) 1992-03-02 1993-03-02 Dental impression materials containing quadri-functional siloxane polymers

Country Status (1)

Country Link
WO (1) WO1993017654A1 (en)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996032088A1 (en) * 1995-04-13 1996-10-17 Dentsply International Inc. Improved polyvinylsiloxane impression material
WO1997040102A1 (en) * 1996-04-18 1997-10-30 A. Kettenbach Fabrik Chem. Erzeugnisse Dental-Spezialitäten Gmbh & Co. Kg Addition cross-linking, two-component silicone materials
WO1997049767A1 (en) * 1996-06-26 1997-12-31 Wacker-Chemie Gmbh Crosslinkable organopolysiloxane materials
US5830951A (en) * 1995-04-13 1998-11-03 Dentsply Detrey G.M.B.H. Polyvinylsiloxane impression material
WO1998053791A2 (en) * 1997-05-29 1998-12-03 Dentsply International Inc. Improved polyvinylsiloxane impression material
DE19730515A1 (en) * 1997-07-16 1999-01-21 Espe Dental Ag Impression material based on silicone
US5955513A (en) * 1995-04-13 1999-09-21 Dentsply Research & Development Corp. Very high viscosity polyvinylsiloxane impression material
US6552104B1 (en) 1995-04-13 2003-04-22 Dentsply Research & Development Corp. Method of making hydrophilic non-sweating polymerizable dental impression material
US6561807B2 (en) 1998-05-27 2003-05-13 Dentsply Research & Development Corp. Polyvinylsiloxane impression material
JP2005272844A (en) * 2004-03-23 2005-10-06 Wacker Chemie Gmbh Crosslinkable material based on organosilicon compound
EP1707179A1 (en) * 2005-03-31 2006-10-04 GC Corporation Impression material composition for recording occlusion
US8066512B2 (en) 2008-10-22 2011-11-29 Millstein Philip L Method for occlusal position measurement and recording
US20120225402A1 (en) * 2011-03-04 2012-09-06 Crivello James V Novel dental appliances and methods for their fabrication
US20130267628A1 (en) * 2010-12-13 2013-10-10 Bluestar Silicones France Silicone elastomer material suitable for use in particular for making dental impressions
KR101458797B1 (en) 2013-04-29 2014-11-07 (주) 베리콤 Dental Impression Materials of Improved Mechanical Properties
WO2017040726A1 (en) * 2015-09-03 2017-03-09 Centrix, Inc. One step gingiva retraction and impression material and method

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3950300A (en) * 1972-10-11 1976-04-13 Wacker-Chemie Gmbh Dental impression materials
US4035453A (en) * 1974-05-28 1977-07-12 Wacker-Chemie Gmbh Dental impression materials
US4222983A (en) * 1977-08-12 1980-09-16 Wacker-Chemie Gmbh Impression compositions and process for preparing impressions
US4609687A (en) * 1984-02-21 1986-09-02 Bayer Aktiengesellschaft Modified fillers for silicone dental pastes
US5064891A (en) * 1989-05-19 1991-11-12 Shin-Etsu Chemical Co., Ltd. Curable silicone compositions

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3950300A (en) * 1972-10-11 1976-04-13 Wacker-Chemie Gmbh Dental impression materials
US4035453A (en) * 1974-05-28 1977-07-12 Wacker-Chemie Gmbh Dental impression materials
US4222983A (en) * 1977-08-12 1980-09-16 Wacker-Chemie Gmbh Impression compositions and process for preparing impressions
US4609687A (en) * 1984-02-21 1986-09-02 Bayer Aktiengesellschaft Modified fillers for silicone dental pastes
US5064891A (en) * 1989-05-19 1991-11-12 Shin-Etsu Chemical Co., Ltd. Curable silicone compositions

Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5830951A (en) * 1995-04-13 1998-11-03 Dentsply Detrey G.M.B.H. Polyvinylsiloxane impression material
US5661222A (en) * 1995-04-13 1997-08-26 Dentsply Research & Development Corp. Polyvinylsiloxane impression material
US5955513A (en) * 1995-04-13 1999-09-21 Dentsply Research & Development Corp. Very high viscosity polyvinylsiloxane impression material
US5863965A (en) * 1995-04-13 1999-01-26 Dentsply Research & Development Corp. Polyvinylsiloxane impression material
WO1996032088A1 (en) * 1995-04-13 1996-10-17 Dentsply International Inc. Improved polyvinylsiloxane impression material
US6552104B1 (en) 1995-04-13 2003-04-22 Dentsply Research & Development Corp. Method of making hydrophilic non-sweating polymerizable dental impression material
US6313190B1 (en) 1996-04-18 2001-11-06 Kettenbach Gmbh & Co. Kg Addition cross-linking, two-component silicone material with high shore hardness and high modulus of elasticity
WO1997040102A1 (en) * 1996-04-18 1997-10-30 A. Kettenbach Fabrik Chem. Erzeugnisse Dental-Spezialitäten Gmbh & Co. Kg Addition cross-linking, two-component silicone materials
WO1997049767A1 (en) * 1996-06-26 1997-12-31 Wacker-Chemie Gmbh Crosslinkable organopolysiloxane materials
JP2009185303A (en) * 1996-06-26 2009-08-20 Wacker Chemie Ag Crosslinkable organopolysiloxane composition
US6348557B1 (en) * 1996-06-26 2002-02-19 Wacker-Chemie Gmbh Crosslinkable organopolysiloxane materials
WO1998053791A2 (en) * 1997-05-29 1998-12-03 Dentsply International Inc. Improved polyvinylsiloxane impression material
WO1998053791A3 (en) * 1997-05-29 1999-04-15 Dentsply Int Inc Improved polyvinylsiloxane impression material
US6121362A (en) * 1997-07-16 2000-09-19 Espe Dental Ag Silicone-based impression material
DE19730515A1 (en) * 1997-07-16 1999-01-21 Espe Dental Ag Impression material based on silicone
US6561807B2 (en) 1998-05-27 2003-05-13 Dentsply Research & Development Corp. Polyvinylsiloxane impression material
WO1999062461A1 (en) * 1998-06-01 1999-12-09 Dentsply International Inc. Very high viscosity polyvinylsiloxane impression material
JP2005272844A (en) * 2004-03-23 2005-10-06 Wacker Chemie Gmbh Crosslinkable material based on organosilicon compound
JP4612444B2 (en) * 2004-03-23 2011-01-12 ワッカー ケミー アクチエンゲゼルシャフトWacker Chemie AG Crosslinkable material to the organic silicon compound based
EP1707179A1 (en) * 2005-03-31 2006-10-04 GC Corporation Impression material composition for recording occlusion
JP2006282556A (en) * 2005-03-31 2006-10-19 Gc Corp Impression material composition for making bite
US8066512B2 (en) 2008-10-22 2011-11-29 Millstein Philip L Method for occlusal position measurement and recording
US8529254B2 (en) 2008-10-22 2013-09-10 Philip L. Millstein Method and apparatus for occlusal position measurement and recording
US9714345B2 (en) * 2010-12-13 2017-07-25 Bluestar Silicones France Sas Silicone elastomer material suitable for use in particular for making dental impressions
US20130267628A1 (en) * 2010-12-13 2013-10-10 Bluestar Silicones France Silicone elastomer material suitable for use in particular for making dental impressions
US8747109B2 (en) 2011-03-04 2014-06-10 James V. Crivello Dental appliances and methods for their fabrication
US20140315144A1 (en) * 2011-03-04 2014-10-23 James V. Crivello Novel dental appliances and methods for their fabrication
US20120225402A1 (en) * 2011-03-04 2012-09-06 Crivello James V Novel dental appliances and methods for their fabrication
US9795462B2 (en) 2011-03-04 2017-10-24 Ez Tray Llc Dental appliances and methods for their fabrication
KR101458797B1 (en) 2013-04-29 2014-11-07 (주) 베리콤 Dental Impression Materials of Improved Mechanical Properties
WO2017040726A1 (en) * 2015-09-03 2017-03-09 Centrix, Inc. One step gingiva retraction and impression material and method

Similar Documents

Publication Publication Date Title
US3436366A (en) Silicone potting compositions comprising mixtures of organopolysiloxanes containing vinyl groups
US3457214A (en) Low temperature vulcanizing composition and article made therefrom
US4087585A (en) Self-adhering silicone compositions and preparations thereof
US4831070A (en) Moldable elastomeric pressure sensitive adhesives
US4987169A (en) Method of preparing silicon compositions
US5907002A (en) Dental impression silicone composition
US5849812A (en) Addition-crosslinking polyether impression material
US4879339A (en) Storage stable and room temperature-curable organopolysiloxane composition
US5534609A (en) Polysiloxane compositions
US6512072B1 (en) Fast cure film forming formulation
US20020147275A1 (en) Two-step curable mixer-suitable materials
US4970252A (en) Oily paste composition
US5013772A (en) Method for the preparation of silicone rubber composition
US6677393B1 (en) Silicon-based impression compounds with improved non-sag properties
US4543063A (en) Elastomeric impression material for tooth and supporting structure duplication
US6552104B1 (en) Method of making hydrophilic non-sweating polymerizable dental impression material
US5955513A (en) Very high viscosity polyvinylsiloxane impression material
US4468202A (en) Method for making dental impressions
US5302632A (en) High consistency organosiloxane compositions comprising fluorinated and non-fluorinated polyorganosiloxanes
US6121362A (en) Silicone-based impression material
US3897376A (en) Room temperature vulcanizable silicone rubber composition
US3070566A (en) Horzsio
US5824736A (en) Fluorosilicone rubber composition
US4454288A (en) Surface treatment of inorganic fillers
US3950300A (en) Dental impression materials

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): JP

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
122 Ep: pct application non-entry in european phase