EP1926448A2 - Compositions, kits and methods for initiating or accelerating curing of endodontic filler or sealer compositions placed on a root canal - Google Patents
Compositions, kits and methods for initiating or accelerating curing of endodontic filler or sealer compositions placed on a root canalInfo
- Publication number
- EP1926448A2 EP1926448A2 EP06824994A EP06824994A EP1926448A2 EP 1926448 A2 EP1926448 A2 EP 1926448A2 EP 06824994 A EP06824994 A EP 06824994A EP 06824994 A EP06824994 A EP 06824994A EP 1926448 A2 EP1926448 A2 EP 1926448A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- curing
- composition
- sealer
- filler
- curing agent
- 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
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61C—DENTISTRY; APPARATUS OR METHODS FOR ORAL OR DENTAL HYGIENE
- A61C5/00—Filling or capping teeth
- A61C5/50—Implements for filling root canals; Methods or instruments for medication of tooth nerve channels
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61C—DENTISTRY; APPARATUS OR METHODS FOR ORAL OR DENTAL HYGIENE
- A61C5/00—Filling or capping teeth
- A61C5/40—Implements for surgical treatment of the roots or nerves of the teeth; Nerve needles; Methods or instruments for medication of the roots
Definitions
- the present invention relates to concentrated curing compositions for use in initiating or accelerating curing endodontic sealer and filler compositions placed in a person's root canal.
- the invention relates to kits that include a microdose container filled with a concentrated curing composition used to coat or impregnate a
- the root canal is typically cleaned using special root canal tools and irrigation devices. Following such a root canal procedure,
- gutta percha refers to a rubbery material derived from natural rubber and typically blended with zinc oxide. This particular rubbery material is preferred because it is compressible, flexible and relatively soft so that it can be used to fill voids within the exposed root canal.
- the gutta percha cones are typically impregnated with other materials such as radiopaque solids, zinc oxide, for its
- gutta percha Filling a root canal with gutta percha often requires inserting more than one gutta percha point or cone. Most root canals are narrow at the apical end and widen as they move up through the tooth. The first gutta percha point or cone is used to seal the apex and is often referred to as the master cone. Following placement of the
- gutta percha points can be added to fill the increasingly larger void of the root canal.
- flowable materials such as sealing resins
- sealing resins are inserted into the root canal along with the gutta percha points.
- One feature of most sealing resins is the need to harden or cure the resin.
- the sealing resin remains in a liquid state until polymerized by an initiator or curing agent. Because root canals are deep and narrow, photocuring a resin deep within the root canal is not possible.
- a chemical curing agent must be employed. The curing agent is typically mixed with the resin just prior to inserting the resin in the root canal, thereby giving the practitioner the greatest amount of time to work before the resin hardens.
- This inability to modify cure times once curing has been initiated can make certain steps of a root canal procedure difficult or impossible. For example, a practitioner may not have sufficient time to take an X-ray to determine whether the sealing material has successfully filled the entire root canal, including lateral canals and/or whether the gutta percha points have been properly positioned. Alternatively, the curing process may take too much time, thus wasting the patient's and the practitioner's time or making it necessary for the patient to return for a follow up procedure after the resin has fully hardened.
- compositions, kits and methods that can be employed to reliably cure a curable resin placed within a person's root canal while giving the practitioner flexibility to increase or decrease the time the practitioner has to work with the resin while carrying out the dental filling procedure.
- the present invention overcomes the above mentioned problems in the prior art by providing curing compositions, kits and methods that allow a practitioner to control the timing and/or extent of the curing of an endodontic filler or sealer composition within a person's root canal.
- the curing composition is provided in concentrated form so that only a small quantity of the curing composition is required to initiate curing, which typically involves free radical polymerization and/or cross linking of one or more curable resins contained within the filler or sealer composition.
- the curable resins may include monomers, dimers, trimers, oligomers or other polymerizable units having ethylenically unsaturated groups (e.g., acrylic acid, methacrylic acid, or esters thereof).
- a suitably sized implement such as an endodontic point or dental tool, is first coated or impregnated with the curable composition and then placed in the root canal containing the filler or sealer composition.
- coating or impregnating the implement is performed by the dental practitioner just prior to inserting the implement into the root canal.
- the practitioner dips the implement in a vial containing a curing composition in concentrated form (e.g., a curing agent in a solvent or other carrier liquid). Because curing agents can be toxic, the concentrated curing composition is advantageously pre-packaged in a microdose container.
- the curing agent may be pre-coated on or impregnated within the implement, thereby forming an activating implement (e.g., endodontic point or dental tool).
- an activating implement e.g., endodontic point or dental tool
- the endodontic point or dental tool initiates or accelerates polymerization of the sealer or filling material.
- the amount of curing agent pre-coated on or impregnated within the implement will typically be such that a desired level of curing will be attained (e.g., partial or total curing). Nevertheless, it is not so much the amount of curing agent but when the curing agent is first contacted with the filler or sealing composition within the root canal that is the main determining factor regarding the timing and/or extent of curing.
- the curing agent can be any one of a number of components used to cure sealer or filler compositions.
- the curing agent comprises one or more amines that initiate or accelerate polymerization of the sealer or filling composition by destabilizing a peroxide contained within the sealer or filler composition. The destabilized peroxide can then initiate free radical polymerization (e.g., of an acrylate- or methacrylate-based sealer of filler composition).
- the curing agent may comprise one or more peroxides that are initially stable when coated or impregnated onto the implement but which are destabilized by one or more amines contained within the sealer or filler composition.
- Other polymerizable sealer or filler compositions that can be initiated using an appropriate curing agent coated on or impregnated within an implement, such as an endodontic point or dental tool, include epoxy- or cationic-based compositions.
- a kit for use in initiating or accelerating curing of an endodontic filler or sealer composition may include one or more microdose containers, each including an appropriate quantity and/or concentration of curing composition. Because the curing agent can be toxic, particularly in the case of amines, a microdose container containing a very small quantity of the curing composition can be provided.
- microdose containers within the scope of the invention may contain from about 0.01 ml to about 1 ml of the curing composition, preferably from about 0.05 ml to about 0.5 ml, and more preferably from about 0.075 ml to about 0.25 ml. According to one embodiment, the microdose container contains about 0.1-0.15 ml of the curing composition.
- kits having differing concentrations and/or amounts of curing agent in order to provide different cure times.
- a dental practitioner can select an appropriate composition from the kit and dip an implement or substrate into the curing agent composition so as to form the activating implement or substrate just prior to use.
- the dental practitioner can control the cure time by selecting the proper curing agent composition.
- the kit may optionally include one or more implements (e.g., rigid elongated devices, such as plastic or metal rods) that may be coated and/or impregnated with the curing composition prior to inserting an implement within a filler or sealer composition within a root canal to initiate and/or accelerate curing thereof.
- kits within the scope of the invention may include one or more endodontic filler or sealer compositions and one or more microdose containers that contain appropriate amounts and/or concentrations of curing composition (e.g., to provide single or variable cure times).
- the endodontic filler or sealer composition may be pre-packaged within an appropriate container, such as a syringe.
- One or more syringe tips containing a cannula sufficiently narrow to be placed within a root canal may be provided with the kit.
- the filler or sealer compositions may include part of a curing system complementary to the curing composition. They may also comprise two-part chemical cure compositions that include an amount of curing agent when mixed so that only slow curing occurs.
- kits may also include one or more implements as previously discussed.
- kits are provided that include a plurality of implements that are pre-coated or impregnated with a curing agent.
- the implements may include different amounts of curing agent so as to provide different cure times.
- the kit may include endodontic cones that are intended to be sequentially placed into a root canal during a filling or sealing procedure.
- one or more cones that are to be placed first may include an amount of curing agent that only initiates slow curing of the filler or sealer composition.
- One or more cones that are to placed later may include an amount of curing agent that more rapidly cures the filler or sealer composition.
- a kit containing one or more master cones and one or more accessory cones can be used to select when or how fast to initiate the curing process.
- the master cone may be treated with a curing agent to initiate either slow or fast curing.
- Accessory cones designed to be placed into a root canal after the master cone can be treated with a curing agent.
- one or more accessory cones can be used to initiate faster curing.
- only the accessory cones will be treated such that the master cone does not itself initiate curing.
- the present invention also includes methods for performing an endodontic procedure.
- the methods of the present invention include performing a root canal on the tooth of a person or animal to prepare the root canal for a sealer or filling composition, placing a sealer or filler composition in the root canal, and initiating or accelerating the polymerization of the filler or sealer composition by placing an activating endodontic point or dental tool in contact with the sealer of filler composition.
- the method may employ and of the inventive compositions and/or kits disclosed herein to provide a desired rate or extent of curing of the filler or sealer compositions positioned within the root canal.
- compositions, kits and methods of the present invention allow a practitioner to better control when a sealer or filler composition is cured during the endodontic procedure and the time within which curing will occur.
- a practitioner can prepare and place a curable sealer or filling material in the root canal and wait for a desired amount of time before initiating or causing complete polymerization and/or cross linking.
- the practitioner can control the timing of curing by selecting when to place the activating endodontic point or dental tool in the sealer or filler material.
- the rate of polymerization can also be controlled.
- the present invention allows for complete curing along the entire root canal.
- One advantage of controlling cure timing is that the practitioner can choose to perform a step, such as taking X-rays, to determine proper placement of the filler or sealer material and/or endodontic point (e.g., a master cone). Because the practitioner can select when to cause curing of the sealer or filler material, the practitioner can cause very rapid curing after performing any necessary prep work. This allows subsequent procedures, such as restorative procedures, to be performed immediately following the sealing or filling procedure. For example, this feature can allow a patient to receive a root canal and a restorative post procedure in a single office visit.
- a step such as taking X-rays
- Figure 1 illustrates an exemplary tooth with its root prepared in an endodontic procedure for sealing and filling according to an exemplary embodiment of the 15 present invention
- Figure 2 illustrates placement of an endodontic point in the apex of the tooth of Figure 1;
- Figure 3 illustrates filling the root canal of the tooth of Figure 2 with an endodontic sealer or filler composition
- Figure 4 Illustrates the tooth of Figure 2 partially filled with a sealer or filler composition
- Figures 5A and 5B illustrate the act of dipping an endodontic cone into a microdose container that contains therein a microdose of a curing composition
- Figure 6 shows the tooth and filler or sealer composition of Figure 4 with a 25 pair of activating accessory endodontic points placed in the sealer or filler composition to initiate or accelerate curing.
- the invention encompasses compositions, kits and methods used to control the timing and/or extent of curing sealer and filler compositions placed in a root canal
- Curing compositions include a curing agent in concentrated form.
- An implement such as an endodontic point or dental tool can be coated or impregnated with the curing composition and then inserted into a filler or sealer composition positioned within a root canal.
- the endodontic point or dental instrument may be pre-coated or impregnated with a curing agent to form an
- the curing agent When contacted with a sealer or filler composition, the curing agent initiates or accelerates polymerization and/or cross linking of the sealer or filler composition.
- the timing when curing of the endodontic filler or sealer composition can be controlled by selecting when to contact the curable composition with the curing agent. Furthermore, the cure time can be further controlled by controlling the concentration and/or amount of curing agent that is coated on or impregnated within the implement.
- the curing composition can be used to initiate curing of a filler or sealer composition placed in a root canal.
- the curing composition can be used to accelerate curing of a filler or sealer composition placed in a root canal that has already begun to cure but which is curing slowly to provide adequate time for the endodontist to perform desired and/or necessary procedures prior to final cure.
- Curing compositions within the scope of the invention preferably contain one or more curing agents in concentrated form.
- the concentrated form allows a small amount of the curing composition to quickly initiate and/or accelerate curing of a filler or sealer composition within a root canal.
- An appropriate curing agent is selected to initiate or accelerate polymerization of the particular sealer or filler composition being used to fill and/or seal the root canal.
- the curing agent may be one part of a curing system that is capable of polymerizing the sealer or filler composition. Generally, any component of a curing system can be used as the curing agent so long as that compound can initiate and/or accelerate polymerization of the sealer or filler composition.
- the curing agent may be selected to initiate curing of any polymerizable sealant or filler composition, including but not limited to, acrylic acid- and/or methacrylic acid-based compositions, acrylate- and/or methacrylate-based compositions, epoxy-based compositions, and cationic- based compositions.
- the curing agent can be coated on or impregnated within an implement, such as an endodontic cone or dental tool, either prior to or just before use.
- an implement such as an endodontic cone or dental tool
- the curing agent causes polymerization and/or cross linking of the sealer or filler composition.
- the curing agent of the present invention can be a chemical initiator or it can be an additive that works with a chemical initiator to initiate or accelerate polymerization of the sealer or filler composition.
- Chemical initiators are compounds that induce polymerization and/or cross linking (e.g., free radical polymerization and/or cross linking) of the polymerizable material.
- Additives are compounds that react with initiators in order to cause the initiators to induce polymerization and/or cross linking.
- Examples of chemical initiators that induce free radical polymerization and/or cross linking include a wide range of peroxides, other per compounds, and other free radical generators.
- Exemplary peroxides include benzoyl peroxide, 2-butanone peroxide, lauroyl peroxide and tert-butyl peroxide.
- Peroxides are typically stable, or can be made stable, until it is desired to initiate free radical polymerization and/or cross linking.
- An additive is used to destabilize the peroxide, causing free radicals to be generated that are able to then induce polymerization and/or cross linking of the curable composition (e.g., by means of free radical induced polymerization and/or cross linking of ethylenically unsaturated groups contained in the polymerizable units).
- additives that can be used to destabilize peroxide initiators include a wide variety of amines (i.e., amino compounds).
- amino compounds include dimethylamino ethyl methacrylate, triethyl amine, 2- dimethylamino ethanol, diethylamino ethyl methacrylate, trihexyl amine, N 5 N- dimethyl-p-toluidine (also referred to as DMPT), N-methylethanolamine, 2,2'(p- tolyimino) diethanol (also referred to as P-TIDE), and derivatives thereof.
- DMPT N- dimethyl-p-toluidine
- P-TIDE 2,2'(p- tolyimino) diethanol
- the curing composition applied to a substrate or implement and then inserted into the curable resin to initiate or accelerate curing comprises an amine or other additive that is able to react with and destabilize a peroxide or other initiator that is already mixed within the curable resin within the root canal.
- the curing composition applied to a substrate or implement and then inserted into the curable resin to initiate or accelerate curing comprises a peroxide or other initiator that is able to react with and become destabilized by an amine or other additive that is already mixed within the curable resin within the root canal.
- the curing agent, whether an initiator or additive, is preferably contained in high concentration within the curing composition, typically as a solution or suspension together with an appropriate solvent or carrier liquid.
- the curing agent may have a concentration in a range of about 25% to 100% by weight of the curing composition, preferably from about 35% to about 75% by weight, and most preferably from about 45% to about 55% by weight.
- Any appropriate solvent or other carrier liquid can be mixed with the curing agent to yield a curing composition having a desired concentration of curing agent.
- a solvent or other carrier is typically selected that does not itself react with the curing agent.
- the solvent may be non-reactive or it may itself be capable of polymerizing.
- the curing composition is preferably fluid and non-viscous to facilitate fast diffusion of the curing composition into the curable composition.
- non- polymerizable solvents and other carriers examples include water, methanol, ethanol, isopropyl alcohol, propylene glycol, 1,3 -propanediol, glycerin, polyethylene glycol, polypropylene glycol, actone, toluene, xylene, ethyl acetate, DMSO, DMF, and acetonitrile.
- An examples of a polymerizable solvent or carrier is triethylene glycol dimethacrylate (TEG-DMA).
- the curing composition can pre-coated on or impregnated within an implement, such as an endodontic cone, to form an activating dental implement or substrate.
- the curing composition that is pre-coated on or impregnated in the implement may simply include a curing agent and solvent or other carrier liquid, as discussed above.
- the curing composition may further include one or more polymerizable materials in order to improve adhesion of the curing agent to the substrate, particularly in the case where the substrate is hydrophobic, such as gutta percha, or otherwise has a tendency to repel the curing agent.
- the curing agent may optionally include a preservative such as a free-radical scavegener, which is especially advantageous in the case where the solvent or carrier is capable of free radical polymerization.
- a free radical scavenger that can be used to prevent premature polymerization of a polymerizable solvent or carrier is butylated hydroxytoluene (BHT). Another is butylated hydroxyanisole (BHA).
- the activating substrate or implement of the present invention is an endodontic point.
- Figure 1 depicts a tooth 10 that has been subjected to a root canal procedure such that a substrate can be inserted therein.
- the tooth 10 includes a root canal 12 in tooth root 14.
- Root canal 12 includes root canal portions 16a and 16b.
- Root canal portions 16a and 16b terminate at apexes 18a and 18b, respectively to create root openings 20a and 20b.
- Lateral canals 22 extend into root 14 from root canal 12.
- An opening 24 in the crown of the tooth provides access to root canal 12.
- the substrate of the present invention is sized and configured to be inserted through opening 24 and into root canal 12.
- the substrate is configured to be inserted into the pulp chamber 26.
- the substrate of the present invention can be sized and configured to be at least partially placed in the root canal portions 16a or 16b.
- substrates that can be inserted into root canal 12 have a diameter between about 0.1 and 1.1 mm for human teeth. Animals however, can have much larger root canals, such as up to about 20 mm.
- the substrate of the present invention is an endodontic point.
- Figure 2 shows endodontic points 28a and 28b inserted into apexes 18a and 18b respectively.
- endodontic points 28a and 28b can be coated or impregnated with a curing agent according to the present invention.
- Endodontic points 28a and 28b can be made of gutta percha and are used for their typical benefit, which is to plug or seal root openings 20a and 20b in root canals 16a and 16b respectively.
- endodontic points 28a and 28b as a substrate according to the present invention has the added benefit of not requiring additional materials or tools to be placed in the root canal.
- This aspect of the invention can be particularly beneficial where the substrate needs to be placed near apex 18 since root canal 16a and 16b can be very narrow at the apex.
- Endodontic points 28a and 28b shown in Figure 2 are master points and can be used as a substrate according to the present invention.
- accessory cones such as endodontic points 38a and 38b can also be used as a substrate.
- accessory cones are typically used to seal lateral canals 22, where the master cones are used to plug the opening in the apex.
- only the accessory cones are activating so that curing is not initiated or accelerated until placement of the accessory cones. This allows a dentist or endodontist to take one or more X-rays to ensure proper placement of the filler or sealer and the master cone(s) prior to initiating or accelerating curing. It is also within the scope of the invention to use a master cone that is treated to initiate either fast or slow curing.
- a dental tool or other device can be used as a substrate.
- syringe 30, shown in Figure 3 e.g., an outer surface of cannula 34
- the substrate can be another dental tool such as an endodontic file (not shown) or thin piece of plastic or other material (not shown) so long as the substrate is sized and configured to be placed into at least a portion of a root canal.
- an endodontic file not shown
- thin piece of plastic or other material not shown
- activating implements are made by dipping the implement or substrate into a composition that includes the curing agent.
- the curing agent is mixed with one or more of a polymer or a solvent, and the substrate is dipped into the polymer or solvent.
- the polymer or solvent can be used as a carrier for coating or impregnating the substrate.
- the substrate is dipped directly into pure curing agent.
- any coating or impregnation method can be used to apply the curing agent to the substrate, using a carrier can be particularly effective.
- using a carrier can provide an appropriate distribution of the curing agent over the substrate.
- a dental tool such as a metal tool
- a polymeric mixture can be used that has a viscous or adhesive property that causes the polymeric mixture to adhere to the dental tool.
- a gutta percha point is used, a solvent can be used that can penetrate the gutta percha and impregnate it. Nevertheless, dental tools and gutta percha endodontic points can be coated using a polymeric material instead of, or in addition to, a solvent.
- a second advantage of using a carrier such as a solvent or polymer to deliver the curing agent is that mixing the curing agent allows the concentration of the curing agent to be controlled.
- the cure time depends on the concentration of the curing agent in the sealer or filler composition. This is accomplished by making the curing agent the limiting reagent or choosing a curing agent that can accelerate the reaction.
- the curing agent is an amine that destabilizes a peroxide in the sealer or filler material. The concentration of the amine in the sealer or filler material determines in large part the magnitude of the cure time.
- Coating or impregnating the substrate by dipping the substrate directly in a curing agent liquid such as P-TIDE or DMPT results in cure times of less than about 30 seconds.
- a curing agent liquid such as P-TIDE or DMPT
- the cure time can be extended to any desired amount of time.
- Suitable polymers useful as a carrier for the curing agent include acrylate based polymers such as methacrylates and di-acrylates.
- the polymers used as a carrier for the curing agent are similar or identical to the polymers used in the sealer or filling material.
- a solvent is typically used to impregnate an endodontic point or dental tool.
- An example of a solvent suitable for using in the present invention is toluene.
- the curing agent is an amine that is included in a polymeric material and the concentration of amine is between about 0.1 and about 35% of the polymeric mixture.
- concentration of curing agent will depend on the curing agent selected.
- P-TIDE is typically used in a range of between about 5% and 35%, and more preferably in a range of about 20% - 25% of the coating.
- a coating having P-TIDE in a concentration of about 20% to about 25% causes the sealer or filler material in the root canal to cure in about 2-4 minutes.
- DMPT is used with the solvent toluene, preferably in a concentration of about 0.1% to about 20%, and more preferably in a concentration of about l%-2%.
- DMPT in a concentration of about 2% in toluene and impregnated on an endodontic point causes curing in about 8 minutes when placed in a sealer or filler in a root canal.
- any portion of the substrate can be coated or impregnated.
- the entire length of the point is coated or impregnated since gutta percha points may be completely inserted into the root canal.
- a dental tool on the other hand is typically only partially inserted into the root canal. Thus, only a portion of the dental tool is typically coated or impregnated so as to not waste the active agent.
- the activating endodontic points and dental tools of the present invention can be coated or impregnated during manufacture.
- a curing agent composition can be provided to the dental practitioner who then mixes and/or dips a substrate in the curing agent composition to prepare the activating endodontic point or dental tool just before use.
- the endodontic sealer and filler compositions used with the inventive curing compositions and activating implements or substrates according to the invention include at least one chemical curable resin material.
- the curable resin is initially in a liquid or shapeable form.
- sealer or filler composition 32 is placed in root canals 16a and 16b. Sealer or filler composition 32 fills root canals 16 such that root canals 16 and lateral canals 22 are sealed off from each other and opening 24. Sealing root canals 16 and lateral canals 22 help prevents bacteria and other microbes from entering root canal 12 or lateral canals 22 and spreading infection or decay within tooth root 14.
- any polymerizable material capable of sealing a root canal can be used with the present invention.
- suitable primary polymerizable resins include a wide range of acrylic acid- and methacrylic acid-containing compounds, acrylates, methacrylates, alkylhydroxy methacrylates, alkylamino methacrylates, exopy-based compositions, cationic-based compositions, and derivatives thereof. More specific examples of polymerizable materials include glycidyl dimethacrylate, 2-hydroxy ethyl methacrylate, 3 -hydroxy propyl methacrylate, 4-hydroxy butyl methacrylate, triethylene glycol dimethacrylate, and polyethylene glycol dimethacrylate.
- An example of an epoxy-based endodontic sealant resin that can be catalyzed using activating endodontic points or tools according to the invention is AH 26, available from Dentsply.
- the polymerizable resin includes an oxyphosphorus alkyl methacrylate, such as bis glycerol dimethacrylate phosphate.
- an oxyphosphorus alkyl methacrylate such as bis glycerol dimethacrylate phosphate.
- examples of other oxyphosphorus alkyl methacrylates within the scope of the invention include bis 2-hydroxy ethyl methacrylate phosphate, phosphate ester of p- hydroxyphenyl methacrylamide, phosphate ester of 3-hydroxy propyl methacrylate, and phosphate ester of 4-hydroxy butyl methacrylate.
- the oxyphosphorus group increases the adhesiveness and water solubility ⁇ i.e., hydrophiliciry) of the resulting resin.
- Diluent monomer suitable for use in the present invention include urethane dimethacrylate, p-hydroxyphenyl methaciylamide, butane diol dimethacrylate, and bisphenol-A-diglycidyl dimethacrylate ("Bis-GMA").
- the primary polymerizable resins are preferably included in a concentration ranging from about 1% to about 90% by weight of the composition, more preferably from about 10% to about 80% by weight, and most preferably from about 20% to about 70% by weight of the composition.
- the diluent monomers may be included in amounts of up to about 95% by weight of the composition, preferably in a range from about 10% to about 80%, and more preferably in a range from about 30% to about 70% by weight of the composition.
- the filler and sealer compositions may include other components or adjuvents as desired to yield compositions having desired properties. Examples include fillers, such as radiopaque fillers, and non-chemically triggered curing initiators that do not themselves initiate polymerization or cross linking absent application of an appropriate curing stimulus (e.g., light or heat).
- the filler or sealer compositions may be heat curable, photo curable, dual curable, or use any other curing process or combination of curing processes to initiate or accelerate curing.
- the curing system typically includes two or more parts that are initially kept separate but which are mixed together to initiate curing.
- one part of the system includes constituents of the resin sealer or filling together with one part of the chemical cure system (e.g., one or more peroxide compounds), while another part includes constituents of the resin sealing with the other half of the chemical cure system (e.g., an amino compound).
- the present invention deviates from such systems in one of several ways.
- a single component chemical curable composition is provided that includes only one part of a two-part chemical cure system.
- the other part of the two-part chemical cure system is provided by the curing composition, as discussed above, and introduced into the curable composition in concentrated form by means of an implement coated or impregnated with the curing agent comprising the other part of the curing system. In this way, curing is not initiated until an activating implement coated or impregnated with the curing agent is contacts with the curable composition.
- curing of a chemical or dual cure composition may already have begun but can be accelerated using an activating implement.
- a two-part chemical cure composition is provided and mixed together prior to placement into the root canal, except that a deficient amount of one part of the curing system is provided so that only partial or slow curing of the composition occurs.
- Curing of the composition may thereafter be accelerated by introducing an additional quantity of the initially deficient part of the curing system ⁇ i.e., curing agent) by means of the activating implement or substrate.
- the curable compositions may be cured in ways other than by chemical curing.
- a photoinitiator is included in order to permit photocuring of at least an upper or more exposed portion of the curable composition within a root canal.
- photoinitiators include camphor quinone, benzoin methyl ether, 2-hydroxy-2-methyl-l -phenyl- 1-propanone, diphenyl 2,4,6-trimethylbenzoyl phosphine oxide, benzoin ethyl ether, benzophenone, 9,10-anthraquinone, and derivatives thereof.
- photoinitiators are preferably included in an amount in a range from about 0.05% to about 5% by weight of the composition, more preferably in a range from about 0.1% to about 2% by weight, and most preferably in a range from about 0.2% to about 1% by weight of the composition.
- the polymerizable resin is advantageously stable in the presence of the photoinitiator absent the application of radiant energy.
- inventions and dental tools of the present invention can be advantageously used in an endodontic procedure to control the cure times of the endodontic sealer or filler composition.
- Figures 1-4 illustrate a tooth in various steps of an endodontic procedure.
- Figure 1 shows tooth 10 with root canal 12 that has been prepared using known endodontic techniques.
- master endodontic points 28a and 28b are placed in root openings 20a and 20b respectively.
- a procedure involving "tug back" is preferably performed.
- One of ordinary skill in the art of endodontics will know when there is sufficient tug back to confirm an adequate seal of the apexes 18a and 18b by master endodontic cones 28a and 28b. Sufficient tug back indicates that the fit between the gutta percha cone and the apex is sufficiently tight to adequately seal the apex and prevent flow of sealer or filling material into the surrounding bone tissue.
- Figure 3 depicts syringe 30 having a narrow diameter cannula 34 attached to tip 36 of syringe 30 used to insert sealer or filling material into root canal 12. Due to the narrow opening of the cannula 34, and because typical sealer or filling materials are often viscous, it can be advantageous for syringe 30 to be attached to a high pressure hydraulic injection system. Examples of high pressure hydraulic syringes or systems are set forth in U.S. Patent No. 6,425,885, which is assigned to Ultradent, Inc. Examples of narrow cannulas sized for entry into a root canal are set forth in U.S. Pat. No. 6,079,979, which is assigned to Ultradent Products, Inc.
- the tip of the cannula 34 is initially placed within the root canal 12 near one of the apexes 18a or 18b and sealer or filling material 32 ( Figure 4) is injected into root canal 12. As the resinous material begins and continues to fill up the root canal portion 16b, the cannula 34 is slowly raised or withdrawn. This manner of filling the root canal 12 with resinous material minimizes or eliminates the formation of air pockets or bubbles as the resin is progressively placed within the root canal 12. This procedure greatly improves the ability of the resin to initially purge most or all of the air from within the root canal 12. As shown in Figure 4, accessory points 38a and 38b are inserted into root canal 12 to seal the root and/or deliver sealing material 30.
- One or both accessory points 38a and 38b can be treated with a curing agent to initiate or accelerate curing.
- the sealer or filler composition is placed in root canal 12 by first dipping the endodontic points in a resin and then inserting the point into the root canal. When the endodontic point is dipped, resin is coated thereon and is carried into the root canal with the endodontic point.
- some or all of the sealer or filler composition is introduced into the root canal using a master cone.
- some or all of the sealer of filler composition can be introduced into the root canal using one or more accessory cones.
- the endodontic cones can be treated to initiate curing.
- the accessory cones may be treated with a curing agent and used to initiate curing.
- the master cone may be treated so as to initiate curing after insertion of the composition-laden accessory cone(s).
- Controlling the curing time of an endodontic sealer or filling material according to the present invention is accomplished by either (i) selecting when to place an activating implement, such as endodontic point or dental tool, in the curable sealer or filling material, and/or (ii) selecting an activating endodontic point or dental tool with a predetermined amount or concentration of curing agent.
- an activating implement such as endodontic point or dental tool
- the first aspect of controlling curing according to the present invention enables a practitioner to delay curing of the sealer of filler composition by choosing when to place the activating implement in contact with the sealer or filler composition 32.
- accessory endodontic points or cones 38a and 38b are used by the practitioner to control curing of the endodontic sealer or filler composition.
- sealer or filler composition 32 contains little or no of the curing agent needed to initiate curing when it is placed in the root canal.
- the master endodontic cones 28a and 28b are not activating and therefore do not initiate or accelerate curing.
- the practitioner can have any amount of time to place the sealer or filler material 32.
- the practitioner has time to perform other desired procedures. For example, the practitioner can take X-rays of tooth 10 to determine whether the master endodontic points 28a and 28b have properly sealed the apex and/or whether the sealer or filler material has been properly placed in root canal 12 and/or lateral canals 22.
- an activating implement is form in situ by dipping a substrate into a microdose container containing a small amount of a concentrated curing composition.
- An exemplary microdose container 50 is depicted in Figure 5A.
- the container 50 includes an elongate chamber 52 that has an interior diameter that accommodates insertion therein of an endodontic cone 54 (e.g., gutta percha) or other similarly sized implement (not shown) that can be inserted into a root canal.
- a lid 56 is provided for initially sealing the curing composition prior to use. Wings 58 may be provided to enhance grip and control of the relatively small sized container 50 by the practitioner.
- the lid 56 may be a screw cap that is able to screw over corresponding threads of the container 50.
- the activating implement is formed by removing lid 56 and inserting endodontic cone 54 or other implement into the elongate chamber in order to coat the surface of the endodontic cone 54 or other implement with the curing composition.
- an activating implement is inserted into the root canal in order to initiate or accelerate curing of the sealing resin contained in the root canal.
- activating accessory endodontic points 38a and 38b can be placed in root canal 12 as shown in Figure 6.
- the curing agent coated on or impregnated within accessory endodontic points 38a and 38b comes into contact with the sealer or filler composition and initiates curing. Because the practitioner has already had time to perform necessary procedures, sufficient curing agent can be included such that accessory points 38a and 38b cause sealer or filling material 32 to cure very rapidly.
- the accessory points can be made according to any of the methods described above.
- the accessory points can be pre-coated or impregnated during manufacture, or they can be activated just prior to use.
- a dental tool such as syringe 30 can be used to initiate or increase curing of the sealer or filler material.
- the practitioner can dip a syringe cannula 34 in a curing material and then place the coated syringe in contact with the sealer or filler composition.
- the activating dental tool can be an endodontic file or other narrow gauge structure that is able to be inserted at least partially into a root canal.
- the activating dental tool can be an implement or substrate that is simply a piece of plastic or other material that is made activating by applying a curing agent thereto. At least a portion of the plastic or other material is sized and configured to be placed in the root canal of a person or animal such that it can be inserted into the root canal and placed in contact with the sealer or filler composition.
- the circumstances of the procedure will determine which activating endodontic point or dental tool the practitioner will use.
- One advantage of a dental tool such as a piece of plastic is that it can be used at anytime without regard to its use in the dental procedure.
- placement of an endodontic point is sometimes determined according to the needs of the procedure.
- using an activating endodontic point can be advantageous because the endodontic point is intended to permanently remain in the cured product.
- kits for use in initiating or accelerating curing of an endodontic filler or sealer composition may include one or more microdose containers, each containing an appropriate quantity and/or concentration of curing composition.
- a dental practitioner can select an appropriate composition from the kit and dip an implement or substrate into the curing agent composition so as to form the activating implement or substrate just prior to use. The dental practitioner can control the cure time by selecting the proper curing agent composition.
- one or more containers containing one or more different quantities and/or concentrations of curing composition are provided together with one or more implements (e.g., gutta percha cones and/or rigid elongated devices, such as narrow plastic or metal rods, able to fit into a root canal).
- the one or more implements may be coated and/or impregnated with the curing composition by the practitioner just prior to inserting an implement within a filler or sealer composition placed within a root canal to initiate and/or accelerate curing thereof.
- kits within the scope of the invention may include one or more endodontic filler or sealer compositions and one or more microdose containers that contain appropriate amounts and/or concentrations of curing composition (e.g., to provide single or variable cure times).
- the endodontic filler or sealer composition may be pre-packaged within an appropriate container, such as a syringe.
- One or more syringe tips containing a cannula sufficiently narrow to be placed within a root canal may optionally be provided with the kit.
- the curing composition may include, as the "curing agent", one part of a multi-part curing system.
- the filler or sealer compositions may include another part of the multi-part curing system complementary to the curing agent within the curing composition.
- kits may also comprise two-part chemical cure compositions that include a deficient amount of curing agent when mixed so that only slow or incomplete curing occurs. The curing composition is then used to merely accelerate rather than initiate curing.
- kits may optionally include one or more implements as previously discussed.
- kits may be provided that include a plurality of implements that are pre-coated or impregnated with a curing agent.
- the implements may include different amounts of curing agent so as to provide different cure times.
- the kit may include endodontic cones that are intended to be sequentially placed into a root canal during a filling or sealing procedure.
- one or more cones that are to be placed first may include an amount of curing agent that only initiates slow curing of the filler or sealer composition.
- One or more cones that are to placed later may include an amount of curing agent that more rapidly cures the filler or sealer composition.
- a kit containing one or more master cones and one or more accessory cones can be used to select when or how fast to initiate the curing process.
- the master cone may be treated with a curing agent to initiate either slow or fast curing.
- Accessory cones designed to be placed into a root canal after the master cone can be treated with a curing agent.
- one or more accessory cones can be used to initiate faster curing.
- only the accessory cones will be treated such that the master cone does not itself initiate curing.
- the plurality of activating endodontic points and/or dental tools can have different concentrations of the curing agents and are included in a kit.
- the endodontic points or dental tools have different concentrations of curing agent that correspond to different cure times.
- the dental practitioner can select an activating endodontic point or dental tool that provides the proper cure time for that particular procedure.
- the present invention provides the practitioner with the ability to select any desired curing time during the procedure. If the practitioner needs 1 minute, 10 minutes, 2 hours or any other amount of time, the practitioner can select an activating endodontic point or dental tool with a curing agent in a concentration that provides the desired cure time.
- the endodontic filling or sealing composition will be a chemical cure composition having an initial cure time of about 15 minutes or more (e.g. EndoREZ®, which is sold by Ultradent Products, Inc.).
- the activating implements are preferably formulated so as to reduce the cure time to about 5 minutes or less.
- the activating endodontic points and dental tools of the present invention can provide convenience. For example, a practitioner may want to use an activating master endodontic point even though curing would begin as soon as the sealer or filler composition is placed in the root canal. In this embodiment, the practitioner can eliminate the need to mix the sealer or filler composition, thus making the endodontic procedure more convenient. Furthermore, the practitioner can be provided with a set of activating endodontic points that give the practitioner a selection of different concentrations of curing agent and thus different cure times.
- the present invention is also not limited with respect to use of a single activating endodontic point or dental tool during an endodontic procedure.
- an activating master endodontic point can be used with an activating accessory endodontic point.
- the master endodontic point can initiate relatively slow curing and the accessory endodontic point can be used to accelerate curing.
- a master endodontic point, an accessory endodontic point, and/or a dental tool can be used to cure the sealer or filling material.
- Each activating point or tool can be coated and/or impregnated with the same or differing concentrations of curing agent and can be placed in contact with the same or different portions of the sealer or filling material.
- the present invention also includes using more than one type of curing system.
- a chemical curing system can be used in conjunction with a heat curing system or a light curing system.
- the coating provides for better adhesion between the curing agent and a gutta percha cone. Diluting the curing agent in the acrylate resin also gives the coating a desired cure time.
- the acrylate resin coating used in the formulas of examples 2-5 is prepared by first preparing a prepolymer mixture according to the following formula: Krasol LBH 2000 (linear polybutadiene polymer with hydroxyl end groups) 80.499% Dabc LBH 2000 (tin catalyst) 0.001%
- the prepolymer formed using the foregoing components is used to form an acrylate resin coating according to the following formula:
- the prepolymer and the 2-hydroxyethyl acrylate are allowed to react to completion and are then directly mixed with the polyethylene glycol diacrylate to form the Acrylate Resin Coating.
- an endodontic point was coated or impregnated with the curing composition and then placed in an acrylate-based sealer or filler composition in order to initiate curing.
- the acrylate-based sealer or filler composition included benzoyl peroxide as an initiator.
- the amount of sealer or filler composition used in the study was similar to the amount that would occupy a typical root canal.
- a curing composition used to coat an endodontic cone was made by mixing together the following components:
- An endodontic cone made from gutta percha was coated or impregnated with the foregoing curing composition.
- the curing composition was solidified using light initiated curing.
- the coated endodontic cone was placed into a quantity of filler or sealer composition constituting a typical amount found within a root canal.
- the amine curing agent caused the sealer or filler composition to cure in about 2 minutes at 37 0 C.
- a curing composition used to coat an endodontic cone was made by mixing together the following components: Acrylate Coating 97.5%
- An endodontic cone made from gutta percha was coated or impregnated with the foregoing curing composition.
- the curing composition was solidified using light initiated curing.
- the coated endodontic cone was placed into a quantity of filler or sealer composition constituting a typical amount found within a root canal.
- the amine curing agent caused the sealer or filler composition to cure in about 8 minutes at 37 0 C.
- Example 4 A curing composition used to coat an endodontic cone was made by mixing together the following components:
- Irgacure 0.5% An endodontic cone made from gutta percha was coated or impregnated with the foregoing curing composition.
- the curing composition was solidified using light initiated curing.
- the coated endodontic cone was placed into a quantity of filler or sealer composition constituting a typical amount found within a root canal.
- the amine curing agent caused the sealer or filler composition to cure in about 18 minutes at 37 0 C.
- the activating endodontic cone made according to this example gave inconsistent results.
- a curing composition used to coat an endodontic cone was made by mixing together the following components: Toluene 90.0%
- An endodontic cone made from gutta percha was impregnated with the foregoing composition by briefly immersing the endodontic cone in the solution and then allowing the solvent to volatize. The endodontic cone was then placed in the sealer or filler composition, which caused curing in about 3 minutes at 37 0 C. The P- TIDE degraded over time, thus reducing the effectiveness of the activating endodontic cone over a periods of several months.
- An endodontic cone was impregnated with the following curing composition by immersing the endodontic cone in the composition.
- the endodontic cone was placed in a sealer or filler composition, which accelerated to initial curing time from 15 minutes to 5 minutes at 37 0 C.
- An endodontic cone is impregnated with the following curing composition by immersing the endodontic cone in the composition.
- the endodontic cone is placed in a sealer or filler composition in order to accelerate curing.
- TEG-DMA 74.9%
- An endodontic cone was impregnated with the following curing composition by immersing the endodontic cone in the composition.
- Methyl Hydroquinone (stabilizer) 0.03% The endodontic cone was placed into EndoREZ and was able to accelerate the curing time from 15-30 minutes down to 3-5 minutes.
- An endodontic cone was impregnated with the following curing composition by immersing the endodontic cone in the composition.
- the endodontic cone was placed into EndoREZ and was able to accelerate the curing time from 15-30 minutes down to 3-5 minutes.
- An endodontic cone was impregnated with the following curing composition by immersing the endodontic cone in the composition.
- the endodontic cone was placed into EndoREZ and was able to accelerate the curing time from 15-30 minutes down to about 3 minutes.
- An endodontic cone was impregnated with the following curing composition by immersing the endodontic cone in the composition.
- the endodontic cone was placed into EndoREZ and was able to accelerate the curing time from 15-30 minutes down to about 3 minutes.
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- General Health & Medical Sciences (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Surgery (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
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- Dental Tools And Instruments Or Auxiliary Dental Instruments (AREA)
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP13004624.6A EP2684537A1 (en) | 2005-09-21 | 2006-09-15 | Compositions, kits, and methods for initiating or accelerating curing of endodontic filler or sealer compositions placed on a root canal |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/232,062 US7828550B2 (en) | 2005-09-21 | 2005-09-21 | Activating endodontic points and dental tools for initiating polymerization of dental compositions |
US11/530,787 US7863349B2 (en) | 2005-09-21 | 2006-09-11 | Compositions, kits and methods for initiating or accelerating curing of endodontic filler or sealer compositions placed on a root canal |
PCT/US2006/036298 WO2007038051A2 (en) | 2005-09-21 | 2006-09-15 | Compositions, kits and methods for initiating or accelerating curing of endodontic filler or sealer compositions placed on a root canal |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP13004624.6A Division EP2684537A1 (en) | 2005-09-21 | 2006-09-15 | Compositions, kits, and methods for initiating or accelerating curing of endodontic filler or sealer compositions placed on a root canal |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1926448A2 true EP1926448A2 (en) | 2008-06-04 |
EP1926448A4 EP1926448A4 (en) | 2010-02-17 |
Family
ID=37900246
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP06824994A Ceased EP1926448A4 (en) | 2005-09-21 | 2006-09-15 | Compositions, kits and methods for initiating or accelerating curing of endodontic filler or sealer compositions placed on a root canal |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP1926448A4 (en) |
AU (1) | AU2006295136B2 (en) |
WO (1) | WO2007038051A2 (en) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5177121A (en) * | 1981-02-13 | 1993-01-05 | Minnesota Mining And Manufacturing Company | Dentin and enamel adhesive |
EP1375619A1 (en) * | 2002-06-28 | 2004-01-02 | Centrix, Inc. | Contact cure dental post cement and method of placing a dental post |
US20050196726A1 (en) * | 2002-04-23 | 2005-09-08 | Fischer Dan E. | Hydrophilic endodontic sealing compositions and methods for using such compositions |
-
2006
- 2006-09-15 AU AU2006295136A patent/AU2006295136B2/en not_active Ceased
- 2006-09-15 EP EP06824994A patent/EP1926448A4/en not_active Ceased
- 2006-09-15 WO PCT/US2006/036298 patent/WO2007038051A2/en active Application Filing
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5177121A (en) * | 1981-02-13 | 1993-01-05 | Minnesota Mining And Manufacturing Company | Dentin and enamel adhesive |
US20050196726A1 (en) * | 2002-04-23 | 2005-09-08 | Fischer Dan E. | Hydrophilic endodontic sealing compositions and methods for using such compositions |
EP1375619A1 (en) * | 2002-06-28 | 2004-01-02 | Centrix, Inc. | Contact cure dental post cement and method of placing a dental post |
Non-Patent Citations (1)
Title |
---|
See also references of WO2007038051A2 * |
Also Published As
Publication number | Publication date |
---|---|
WO2007038051A3 (en) | 2009-04-30 |
AU2006295136A1 (en) | 2007-04-05 |
AU2006295136B2 (en) | 2013-01-17 |
WO2007038051A2 (en) | 2007-04-05 |
AU2006295136A2 (en) | 2008-05-22 |
EP1926448A4 (en) | 2010-02-17 |
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