(19)
(11)EP 2 114 292 B1

(12)EUROPEAN PATENT SPECIFICATION

(45)Mention of the grant of the patent:
29.04.2020 Bulletin 2020/18

(21)Application number: 08730463.0

(22)Date of filing:  22.02.2008
(51)International Patent Classification (IPC): 
A61C 3/16(2006.01)
A61C 5/30(2017.01)
A61C 5/70(2017.01)
A61K 6/083(2006.01)
A61K 6/00(2020.01)
A61C 5/64(2017.01)
A61C 13/00(2006.01)
A61C 13/107(2006.01)
(86)International application number:
PCT/US2008/054666
(87)International publication number:
WO 2008/106366 (04.09.2008 Gazette  2008/36)

(54)

RESIN REINFORCED ZINC POLYCARBOXYLATE TEMPORARY CEMENT COMPOSITIONS AND RELATED KITS

TEMPORÄRE HARZVERSTÄRKTE ZINK-POLYCARBOXYLAT-ZEMENT-ZUSAMMENSETZUNGEN SOWIE ENTSPRECHENDE KITS

COMPOSITIONS DE CIMENT PROVISOIRE À BASE DE POLYCARBOXYLATE DE ZINC RENFORCÉES DE RÉSINE ET TROUSSES ASSOCIÉS


(84)Designated Contracting States:
AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MT NL NO PL PT RO SE SI SK TR

(30)Priority: 28.02.2007 US 680284

(43)Date of publication of application:
11.11.2009 Bulletin 2009/46

(73)Proprietor: Ultradent Products, Inc.
South Jordan, Utah 84095 (US)

(72)Inventors:
  • KENNARD, Gordon
    Cedar Hills, UT 84062 (US)
  • KAWAMOTO, Andy, T.
    Sandy, UT 84070 (US)
  • WAGNER, Jeff
    Sandy, UT 84094 (US)

(74)Representative: Grünecker Patent- und Rechtsanwälte PartG mbB 
Leopoldstraße 4
80802 München
80802 München (DE)


(56)References cited: : 
US-A- 5 154 613
US-A1- 2005 009 946
US-A1- 2006 035 997
US-B2- 7 166 651
US-A1- 2005 004 254
US-A1- 2006 035 997
US-B1- 6 291 548
  
      
    Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention).


    Description

    BACKGROUND OF THE INVENTION


    1. The Field of the Invention



    [0001] The present invention relates to dental restorations. More particularly, the invention relates to temporary cement compositions and related kits for temporarily bonding provisional dental restorative appliances.

    2. The Relevant Technology



    [0002] When a dental practitioner performs a procedure requiring the removal of a tooth or portion of a tooth, it is desirable to replace the tooth or tooth portion with a dental restorative appliance (e.g, a crown or bridge). Because permanent appliances typically take up to several weeks to prepare, the practitioner will sometimes fit a provisional appliance to replace the person's tooth until a permanent appliance is ready. The provisional appliance is intended to be a temporary prosthesis until a permanent appliance can be ordered and fabricated.

    [0003] Because the provisional appliance is only intended for temporary use, it would be an improvement in the art to provide a cement composition and related kits and methods that are specifically configured for temporarily bonding a provisional appliance in place. Such a temporary cement would provide sufficient compressive strength and bonding strength to allow the patient to engage in typical use of their teeth (e.g., biting, chewing, etc.) while also having sufficiently low bonding strength characteristics so as to facilitate easily removal of the provisional appliance by the practitioner when it is desired to replace the provisional appliance with a permanent appliance.

    [0004] US 2005/0009946 A1 discloses a composite resin for a temporary crown or inlay. US 2006/0035997 A1 discloses 3 acrylic and methacrylic acid ester-based polymeric materials containing as flexibilizing and brittleness reducing agents polyalkylene or polyalkyldiene compounds. US 5,154,613 discloses a dental cement for fixing a temporary dental prosthesis comprising plasticizers to increase flow properties of the cement.

    BRIEF SUMMARY OF THE INVENTION



    [0005] The subject-matter of the invention is defined by claim 1. The dependent claims describe preferred embodiments.

    [0006] The present invention is directed to two-part resin-reinforced cement compositions and kits for bonding a dental prosthetic appliance to a tooth. A first part includes an amine activator component and a zinc oxide filler, while a second part includes a polymerization initiator (e.g., benzoyl peroxide) and a polymerizable component having a structure including at least one acrylate or methacrylate group at one end and a carboxylic acid group at another end. Such a molecule may have a linear structure so as to have just two ends, or it may be branched, so as to have more than just two ends. The two parts are initially separate and then mixed together when it is desired to perform the temporary bonding. Upon mixing the components together, the amine component destabilizes the initiator, initiating curing of the pulymerizable component. The zinc oxide filler reacts with the carboxylic acid group of the polymerizable component to further cure the polycarboxylate temporary cement composition.

    [0007] The cement is a temporary cement composition used for temporarily bonding a provisional dental prosthetic appliance to a tooth. Such a temporary cement is advantageously relatively weak so as to allow easy removal of a provisional prosthetic and the composition. The bonding strength and, optionally, the compressive strength is reduced to a desirable level by inclusion of a plasticizer and, optionally, an un-reactive filler. The plasticizer is included so as to comprise between 15% and 70% by weight of the composition, preferably between about 25% and about 60% by weight of the composition, and more preferably between about 30% and about 40% by weight of the composition. In examples including an un-reactive filler, the un-reactive filler is preferably included so as to comprise between about 3% and about 30% by weight of the composition, more preferably between about 5% and about 25% by weight of the composition, and most preferably between about 7% and about 20% by weight of the composition. In one currently preferred embodiment, both a plasticizer and un-reactive filler are included so as to collectively comprise at least about 35%, more preferably at least about 40% by weight of the composition, which the inventors have found advantageously decreases bonding strength (and compressive strength if a plasticizer is included) of the composition as compared to a composition not including these components. For example, the plasticizer acts to reduce compressive and bonding strength as it weakens the cross-linked matrix structure of the resin reinforced zinc polycarboxylate cement, while the un-reactive filler (e.g., a ceramic) serves to reduce cost and provide a desired viscosity. The un-reactive filler may also act to increase compressive strength and/or decrease bonding strength as compared to a composition where all else is equal but without the un-reactive filler.

    [0008] Contrasted with typical cement compositions, which have compressive strengths of, for example, 100 MPa or more, the inventive temporary cement compositions have a compressive strength that is typically not greater than about 70 MPa, more preferably not greater than 60 MPa, more preferably not greater than about 30 MPa, and most preferably not greater than about 20 MPa. The inventive compositions have a relatively low bonding strength not greater than 3 MPa, preferably not greater than about 2.5 MPa, and more preferably between about 0.2 MPa and about 2 MPa, even more preferably between about 0.2 MPa and about 1 MPa. Such reduced bonding strength advantageously allows the practitioner to easily remove the temporary cement and a provisional appliance restoration when needed (e.g., once the permanent appliance is ready for installation).

    [0009] These and other advantages and features of the present invention will become more fully apparent from the following description and appended claims, or may be learned by the practice of the invention as set forth hereinafter.

    BRIEF DESCRIPTION OF THE DRAWINGS



    [0010] To further clarify the above and other advantages and features of the present invention, a more particular description of the invention will be rendered by references to specific embodiments thereof, which are illustrated in the appended drawings. It is appreciated that these drawings depict only typical embodiments of the invention and are therefore not to be considered limiting of its scope. The invention will be described and explained with additional specificity and detail through the use of the accompanying drawings in which:

    Figures 1A-1B illustrate exemplary systems including means for dispensing the inventive two-part temporary cement composition;

    Figure 2A illustrates a plurality of teeth, one of which is in need of restoration;

    Figure 2B shows the broken tooth of Figure 2A having been reduced and the resulting surface prepared in preparation for bonding a provisional dental prosthetic appliance;

    Figure 2C illustrates an exemplary mixed temporary cement composition being applied to the prepared tooth surface of Figure 2B;

    Figure 2D illustrates a provisional dental prosthetic appliance being positioned for bonding;

    Figure 2E illustrates the provisional dental appliance bonded to the broken tooth with the inventive temporary cement composition;

    Figure 3A illustrates the provisional dental appliance being removed from the broken tooth so as to allow placement and bonding of a permanent restoration; and

    Figure 3B illustrates the permanent restoration bonded to the broken tooth substrate.


    DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS


    I. Introduction



    [0011] The present invention is directed to a two-part resin-reinforced cement composition and related kits for bonding a dental prosthetic appliance to a tooth. The inventive composition is provided in two parts. A first part includes an amine activator component and a zinc oxide filler, while a second part includes a polymerization initiator (e.g., benzoyl peroxide) and a polymerizable component having a structure including at least one acrylate or methacrylate group at one end and a carboxylic acid group at another end. Such a molecule may have a linear structure so as to have just two ends, or it may be branched, so as to have more than just two ends. The two parts are initially separate, and are mixed together just prior to temporarily bonding the provisional restoration. Upon mixing, the amine component destabilizes the initiator, initiating curing of the polymerizable component. The zinc oxide reacts with the carboxylic acid group to further cure the polymerizable component.

    II. An Exemplary Two-Part Temporary Cement Composition



    [0012] The cement composition is provided in a chemical cure two part system. A chemical cure system is advantageous as it allows the cement composition to cure even when not accessible to curing light wavelengths (i.e., it can be quite difficult to effectively light cure through a temporary crown or other provisional appliance). The first part advantageously includes an amine activator component (e.g., a tertiary amine) and a zinc oxide filler. Exemplary amine activator components include 2,2-(p-Tolylimino)diethanol (P-TIDE), a tertiary amine available from Sigma Aldrich, located in St. Louis, Missouri. Other exemplary tertiary amines that may be used include, but are not limited to N, N-Dimethyl-p-toluidine (DMPT) or Ethyl 4-(Dimethylamino)Benzoate (EDMAB).

    [0013] The amine activator component is preferably included in an amount ranging from about 0.01% to about 3% by weight of the composition, more preferably between about 0.05% to about 2% by weight, and most preferably between about 0.1% and about 1% by weight of the composition.

    [0014] The zine oxide reactive filler is believed to react with the carboxylic acid group of the polymerizable component(s) within the composition so as to form a zinc polycarboxylate chelate structure. For this reason, the zinc oxide is initially separate from the polymerizable component(s) including an acrylate/methacrylate group at one end and a carboxylic acid group at another end. The total zinc oxide content (i.e., both sides together) is preferably in an amount ranging from about 3% to about 50% by weight, more preferably in an amount ranging from about 5% to about 30% by weight, and most preferably in an amount ranging from about 10% to about 20% by weight.

    [0015] The second part of the two-part composition includes a polymerization initiator (e.g., a peroxide) and a polymerizable component having a structure including at least one acrylate and/or methacrylate group at one end (e.g., a HEMA group) and a carboxylic acid group at another end. The initiator (e.g., benzoyl peroxide, 2-butanone peroxide, lauroyl peroxide, tert-butyl peroxide) is preferably included in an amount ranging from about 0.01% to about 3% by weight of the composition, more preferably between about 0.05% to about 2% by weight, and most preferably between about 0.1% and about 1% by weight of the composition.

    [0016] Examples of such polymerizable components include, but are not limited to mono-2-(methacryloyloxy)ethyl succinate (HEMA Succinate), available from Sigma Aldrich, located in St. Louis, Missouri; and 1,2-benzenedicarboxylic acid mono(2-((2-methyl-1-oxo-2-propenyh)oxy)ethyl) ester phthalic acid 2-hydroxyethyl ester methacrylate (also known as 2-hydroxyethylmethacrylate/phthalic anhydride, available from Esstech, located in Essington, Pennsylvania.

    [0017] Mono-2-(methacryloyloxy)ethyl succinate has the structure shown below:

    and 2-hydroxyethylmethacrylatelphthalic anhydride has the structure shown below:



    [0018] The composition may advantageously include additional polymerizable components, one or more of which may advantageously be capable of cross-linking during polymerization. Examples of such polymerizable components include various diacrylates and/or dimethacrylates, specific examples of which include bisphenol-A glycidyl methacrylate (Bis-GMA), diurethane dimethacrylate (DUDMA), tri-ethylene glycol dimethacrylate (TEGDMA), hydroxyethyl methacrylate (HEMA) and/or glycerol di-methacrylate (GDMA). Cross-linking during polymerization results in increased overall bonding and compressive strength as compared to examples including no cross-linking polymerizable components. Because these cross-linking polymerizable components tend to have relatively high viscosities, it may be advantageous to also include one or more non-cross-linking low viscosity polymerizable components (e.g., hydroxypropylmethacrylate - HPMA) that act as thinning agents so as to reduce the overall viscosity of the part in which it is included and/or the overall composition. In addition, one or more of the polymerizable components may be phosphated so as to increase adhesion of the composition to the tooth tissue.

    [0019] The composition is characterized as having relatively low bonding strength as compared to permanent bonding cements. In some embodiments, compressive strength may also be reduced as compared to permanent bonding cements. Decreased strength (bonding, and, advantageously, compressive) is achieved through inclusion of a significant fraction of plasticizer and, optionally, unreactive filler within the composition. Un-reactive ceramic filler may actually increase compressive strength, while decreasing bonding strength. Plasticizers (e.g., a hydrocarbon such as polybutadiene or a polysorbate such as TWEEN-80) advantageously decrease both compressive and bonding strength.

    [0020] Preferably, a temporary cement composition according to the invention has a compressive strength that is not greater than about 70 MPa, more preferably not greater than about 60 MPa, more preferably not greater than about 30 MPa, and most preferably not greater than about 20 MPa. Compressive strengths within the range of about 15-30 MPa have been found to provide sufficient strength so as to withstand chewing, biting and other forces typically encountered by a provisional dental restoration, while not being so strong as to present difficulties when replacing a provisional restoration with a permanent one.

    [0021] The temporary cement composition has a bonding strength that is not greater than 3 MPa, preferably not greater than about 2.5 MPa, and more preferably not greater than about 2 MPa. Bonding strengths between about 0.2 MPa and about 2 MPa, even more preferably between about 0.2 MPa and about 1 MPa have been found to provide sufficient strength so as to withstand chewing, biting and other forces typically encountered by a provisional dental restoration, while not being so strong as to present difficulties when replacing a provisional restoration with a permanent one.

    [0022] Plasticizers are selected from glycerin, HERCOLYN-D, a hydrogenated methyl ester of rosin marketed by Hercules Chemical Company, aliphatic straight chain hydrocarbons such as polybutadiene, cetyl alcohol, and/or TWEEN-80, a polysorbate. Because of their hydrophobic characteristics, an aliphatic hydrocarbon (e.g., polybutadiene) is particularly preferred as it minimizes absorption of saliva and/or water from within the mouth. Any plasticizer is included in an amount ranging from 15% to 70% by weight of a temporary cement composition, preferably between about 25% to about 60% by weight, and more preferably between about 30% and about 40% by weight of the temporary cement composition.

    [0023] Exemplary un-reactive fillers include, but are not limited to ceramic fillers (e.g. any of various ceramic fillers sold under the trade name ZEODENT) available from J. M. Huber Corporation. Preferably any un-reactive filler is included in an amount ranging from about 3% to about 30% by weight of the composition, more preferably between about 5% to about 25% by weight, and most preferably between about 7% and about 20% by weight of the composition. In one embodiment, the strength reducing plasticizer and/or un-reactive filler collectively comprise at least about 35% by weight of the composition, more preferably at least about 40% by weight of the composition.

    [0024] The second part may further advantageously include water. Water is required by the zinc oxide chelating reaction in which the zinc becomes integrated within the polycarboxylate matrix, and rather than relying on water theoretically available from saliva within the patient's mouth, the water may be directly provided within the second part of the composition. This is further advantageous as the zinc oxide reaction is believed to occur mostly after the polymerization reaction has already been completed, requiring water from saliva to diffuse through the polymerized material in order to participate in the zinc oxide reaction, which can weaken the strength of the polymerization bonds, and/or which can result in an insufficient quantity of water being made available for the reaction. Including water within the composition avoids these disadvantages by shortening overall curing time and improving efficiency and reliability of the cement composition. Water may be included within a range of about 0.05% to about 5% by weight of the composition, more preferably about 0.1% to about 2% by weight, and most preferably about 0.15% to about 0.5% by weight of the composition.

    [0025] Additional components, for example, a rheology modifying component (e.g., fumed silica), colorants, flavorants, inhibitors (e.g., BHT), and other components may additionally be included. The inclusion of a colorant (e.g., a dye or pigment) within one or both parts (e.g., yellow within part 1 and blue within part 2) so as to give each part a color different from the other part is advantageous as it provides a visual indicator that the two parts have been homogeneously mixed together. Examples of suitable pigments include Suncroma yellow iron oxide, available from Sun Chemical located in Parsippany. New Jersey: V-9117 deep tan, V-9115 buff, and 41130A blue spersastain, available from Ferro Corporation, located in Cleveland. Ohio. Additional colorants (e.g., dyes and/or pigments) will be apparent to one skilled in the art.

    III. Examples


    Example 1



    [0026] An exemplary two-part temporary cement composition may be formed by mixing together equal weights of first and second parts as described below:
    Part A:
    P-TIDE 0.5%
    BisGMA 10%
    DUDMA 8%
    Zinc Oxide 25%
    Tween 80 55%
    Fumed silica 1.5%
    Part B:
    Benzoyl Peroxide 0.5%
    HEMA Succinate 8%
    ZEODENT 113 45%
    TEGDMA 8%
    Water 1.5%
    Glycerin 30%
    GDMA (phosphated) 7%

    Example 2



    [0027] An exemplary two-part temporary cement composition may be formed by mixing together equal weights of first and second parts as described below:
    Part A:
    P-TIDE 0.5%
    BisGMA 10%
    TEGDMA 8%
    Zinc Oxide 10%
    Tween 80 70%
    Fumed silica 1.5%
    Part B:
    Benzoyl Peroxide 0.5%
    2-hydroxyethylmethacrylate/ anhydride 10%
    ZEODENT 113 37%
       
    GDMA 8%
    HPMA 10%
    Water 4.5%
    HERCOLYN-D 30%

    Example 3



    [0028] An exemplary two-part temporary cement composition was formed by mixing together equal weights of first and second parts as described below:
    Part A:
    P-TIDE 0.5%
    BisGMA 34%
    TEGDMA 15%
    Zinc Oxide 29%
    ZEODENT 113 19%
    Suncroma yellow iron oxide pigment 0.075%
    V-9117 deep tan pigment 0.05
    V-9115 buff pigment 0.0125
    Fumed silica 2%
    Part B:
    Benzoyl Peroxide 0.4%
    HEMA Succinate 12%
    GDMA (phosphated) 2%
    HPMA 10%
    Polybutadiene 66.57%
    Water 0.5%
    Fumed Silica 7%
    41130A blue spersastain pigment 0.035%
    Almond oil flavorant 1.5%


    [0029] The temporary cement composition was tested and found to have a compressive strength of about 17 MPa and a bonding strength of about 0.6 MPa. Compressive strength was measured by placing the mixed two-part composition into a cylindrical mold and allowed to cure. After curing, the sample was removed from the mold and sanded with sand paper to reduce the cylinder to a cylinder having dimensions of 2.15 mm in height and 2.35 mm in diameter. An INSTRON compressive strength measuring device was used to crush the sample so as to test compressive strength. Bonding strength was measured by performing a simulated "crown pull" test. The crown pull test was performed by shaping a human tooth into a conical shape. Using the cement composition to be tested, a corresponding metal simulated "crown" was cemented onto the tooth. The INSTRON device was used to pull the crown off the tooth so as to test bonding strength. The fracturing occurred within the cement composition (i.e., not at the interface between the simulated metal "crown" and the cement. In measuring both compressive and bonding strength, each test was performed multiple times and the results averaged. In addition, each sample was soaked in water for 24 hours before being broken.

    Example 4



    [0030] An exemplary two-part temporary cement composition was formed by mixing together equal weights of first and second parts as described below:
    Part A:
    P-TIDE 0.5%
    BisGMA 34%
    TEGDMA 15%
    Zinc Oxide 29%
    ZEODENT 113 19%
    Suncroma yellow iron oxide pigment 0.075%
    V-9117 deep tan pigment 0.05
    V-9115 buff pigment 0.0125
    Fumed silica 2%
    Part B:
    Benzoyl Peroxide 0.4%
    HEMA Succinate 12%
    GDMA (phosphated) 2%
    HPMA 10%
    Polybutadiene 56.57%
    Cetyl Alcohol 10%
    Water 0.5%
    Fumed Silica 7%
    41130A blue spersastain pigment 0.035%
    Almond oil flavorant 1.5%


    [0031] The temporary cement composition was tested and found to have a compressive strength of about 29 MPa and a bonding strength of about 0.8 MPa. In measuring compressive strength and bonding strength, the same mcthology as described in conjunction with Example 3 was used.

    IV. Exemplary Methods of Use



    [0032] Figure 1A illustrates an exemplary system 100 including a first syringe 102a and a second syringe 102b in which the two-part composition is contained. First syringe 102a contains first part 104a of the composition, while second syringe 102b contains second part 104b of the composition. As shown, quantities of each part may be dispensed and mixed on the surface of mixing pad 106 (e.g., with a mixing stick or other suitable tool).

    [0033] Figure 1B illustrates an alternative exemplary combination dispensing and mixing system 100' including a first syringe barrel 102a' and a second syringe barrel 102b' which are integrally connected side by side. Such an apparatus may be injection molded. First barrel 102a' contains first part 104a of the composition, while second syringe 102b' contains second part 104b of the composition. As shown, quantities of each part may be dispensed in an already mixed state as composition 104 from mixing and dispensing tip 105' onto pad 106.

    [0034] Figure 2A is a perspective view of several of a person's teeth including one broken tooth 220 in need of restoration. As shown in Figure 2B, the broken tooth 220 may be reduced and prepared as necessary (e.g., insertion of a post and build up of core material around the post) and the surface may be prepared (e.g., etched and primed) for bonding a provisional dental appliance. As shown in Figures 2C-2D, mixed temporary cement composition 104 may be applied to the prepared tooth surface 222 and/or the corresponding surface 224 of provisional appliance 250a. As shown in Figure 2E, provisional appliance 250a is bonded to tooth substrate 220 with temporary cement 104.

    [0035] Because of its relatively low bonding strength, temporary cement 104 advantageously allows for easy removal of provisional appliance 250a and replacement with a permanent appliance once the permanent appliance has been prepared and is ready for installation. As shown in Figure 3A, pliers or other means may be used to pull off provisional appliance 250a. Because of the relatively low bonding strength of temporary cement composition 104, separation easily and cleanly occurs at the bonding interface 222. The permanent appliance 250b may then be bonded using a permanent bonding cement (Figure 3B).

    [0036] The described embodiments are to be considered in all respects only as illustrative and not restrictive. The scope of the invention is, therefore, indicated by the appended claims rather than by the foregoing description.


    Claims

    1. A two-part resin-reinforced temporary cement composition for temporarily bonding a provisional dental prosthetic appliance to a tooth comprising:

    a first part including an amine activator component and zinc oxide; and

    a second part including a polymerization initiator that is destabilized when mixed with the amine activator component, the second part further including a polymerizable component having a structure including at least one of an acrylate or methacrylate group at one end and a carboxylic acid group at another end, the second part being initially separate from the first part,

    wherein at least one of the first or second parts further comprises a plasticizer selected from glycerin, a hydrogenated methyl ester of rosin, cetyl alcohol, a polysorbate, and/or an aliphatic hydrocarbon in an amount of 15% to 70% by weight of the temporary cement composition so as to reduce the bonding strength of the temporary cement to a value not greater than 3MPa, said bonding strength being measured by performing a simulated "crown pull" test on a conically shaped human tooth onto which a metal simulated "crown" is cemented using the temporary cement composition, wherein an INSTRON device is used to pull the crown off the tooth so as to test the bonding strength.


     
    2. The two-part resin-reinforced temporary cement composition of claim 1, wherein the zinc oxide comprises between 3 percent and 50 percent by weight of the composition.
     
    3. The two-part resin-reinforced temporary cement composition of claim 1, further comprising an un-reactive filler.
     
    4. The two-part resin-reinforced temporary cement composition of claim 1, wherein the polymerizable component having a structure including at least one of an acrylate or methacrylate group at one end and a carboxylic acid group at another end comprises mono-2-(methacryloyloxy)ethyl succinate and/or 2-hydroxyethylmethacrylate/phthalic anhydride having the structure


     
    5. The two-part resin-reinforced temporary cement composition of claim 1, further comprising at least one cross-linking polymerizable component.
     
    6. The two-part resin-reinforced temporary cement of claim 5, wherein the cross-linking polymerizable component comprises at least one member selected from the group consisting of bisphenol-A glycidyl methacrylate, Bis-GMA; diurethane dimethacrylate, DUDMA; triethylene glycol dimethacrylate, TEGDMA; hydroxyethyl methacrylate, HEMA; and glycerol dimethacrylate, GDMA.
     
    7. The two-part resin-reinforced temporary cement composition of claim 5, wherein at least one of the cross-linking polymerizable components is phosphated.
     
    8. The two-part resin-reinforced temporary cement composition of claim 6, further comprising hydroxypropylmethyacrylate, HPMA.
     
    9. The two-part resin-reinforced temporary cement composition of claim 1, further comprising water.
     
    10. The two-part resin-reinforced temporary cement composition of claim 1, further comprising at least one colorant.
     
    11. The two-part resin-reinforced temporary cement composition of claim 1, wherein the aliphatic hydrocarbon is polybutadiene.
     
    12. The two-part resin-reinforced temporary cement composition of claim 3, wherein the plasticizer and the un-reactive filler collectively comprise at least 35 percent by weight of the composition.
     
    13. The two-part resin-reinforced temporary cement composition of claim 3, wherein the un-reactive filler comprises between 3 percent and 30 percent by weight of the composition.
     
    14. The two-part resin-reinforced temporary cement composition of claim 1, wherein the temporary cement has a compressive strength that is not greater than 70 MPa measured by the following method:
    The mixed two-part composition is placed into a cylindrical mold and allowed to cure. After curing, the sample was removed from the mold and sanded with sand paper to reduce the cylinder to a cylinder having dimensions of 2.15 mm in height and 2.35 mm in diameter. An INSTRON compressive strength measuring device is used to crush the sample so as to test compressive strength.
     
    15. The two-part resin-reinforced temporary cement composition of claim 1, wherein the temporary cement has a bonding strength that is not greater than 2.5 MPa, said bonding strength being measured by performing a simulated "crown pull" test on a conically shaped human tooth onto which a metal simulated "crown" is cemented using the temporary cement composition, wherein an INSTRON device is used to pull the crown off the tooth so as to test the bonding strength.
     
    16. A kit for temporarily bonding a provisional dental prosthetic appliance to a tooth comprising:

    a two-part resin-reinforced temporary cement composition as recited in any of claims 1 to 15; and

    a provisional dental prosthetic appliance.


     


    Ansprüche

    1. Zweiteilige harzverstärkte temporäre Zementzusammensetzung zum temporären Befestigen einer provisorischen Zahnprothesevorrichtung an einem Zahn, umfassend:

    einen ersten Teil, der eine Aminaktivatorkomponente und Zinkoxid einschließt; und

    einen zweiten Teil, der einen Polymerisationsinitiator einschließt, der destabilisiert wird, wenn er mit der Aminaktivatorkomponente gemischt wird, wobei der zweite Teil ferner eine polymerisierbare Komponente mit einer Struktur einschließt, die mindestens eine aus einer Acrylat- oder Methacrylatgruppe an einem Ende und eine Carbonsäuregruppe am anderen Ende einschließt, wobei der zweite Teil anfangs vom ersten Teil getrennt ist,

    wobei mindestens einer aus dem ersten oder zweiten Teil ferner einen Weichmacher umfasst, ausgewählt aus Glyzerin, einem hydrogenierten Methylester von Rosin, Cetylalkohol, einem Polysorbat und/oder einem aliphatischen Kohlenwasserstoff, in einer Menge von 15 % bis 70 % bezogen auf das Gewicht der temporären Zementzusammensetzung, um so die Haftfestigkeit des temporären Zements auf einen Wert nicht größer als 3 MPa zu reduzieren, wobei die Haftfestigkeit durch Ausführen eines simulierten "Kronenziehungs"-Tests an einem konisch geformten menschlichen Zahn ausgeführt wird, auf welchen eine simulierte Metall-"Krone" unter Verwendung der temporären Zementzusammensetzung zementiert wird, wobei ein INSTRON-Gerät verwendet wird, um die Krone vom Zahn abzuziehen, um so die Haftfestigkeit zu testen.


     
    2. Zweiteilige harzverstärkte temporäre Zementzusammensetzung nach Anspruch 1, wobei das Zinkoxid zwischen 3 Prozent und 50 Prozent bezogen auf das Gewicht der Zusammensetzung umfasst.
     
    3. Zweiteilige harzverstärkte temporäre Zementzusammensetzung nach Anspruch 1, ferner umfassend einen nicht reaktiven Füllstoff.
     
    4. Zweiteilige harzverstärkte temporäre Zementzusammensetzung nach Anspruch 1, wobei die polymerisierbare Komponente mit einer Struktur, die mindestens eine aus einer Acrylat- oder Methacrylatgruppe an einem Ende und eine Carbonsäuregruppe am anderen Ende einschließt, Mono-2-(methacryloyloxy)ethylsuccinat und/oder 2-Hydroxyethylmethacrylat/Phthalsäureanhydrid mit der Struktur

    umfasst.
     
    5. Zweiteilige harzverstärkte temporäre Zementzusammensetzung nach Anspruch 1, ferner umfassend mindestens eine vernetzende polymerisierbare Komponente.
     
    6. Zweiteiliger harzverstärkter temporärer Zement nach Anspruch 5, wobei die vernetzende polymerisierbare Komponente mindestens ein Mitglied umfasst, ausgewählt aus der Gruppe, bestehend aus Bisphenol-A-Glycidylmethacrylat, Bis-GMA; Diurethandimethacrylat, DUDMA; Triethylenglycoldimethacrylat, TEGDMA; Hydroxyethylmethacrylat, HEMA; und Glycerindimethacrylat, GDMA.
     
    7. Zweiteilige harzverstärkte temporäre Zementzusammensetzung nach Anspruch 5, wobei mindestens eine der vernetzenden polymerisierbaren Komponenten phosphatiert ist.
     
    8. Zweiteilige harzverstärkte temporäre Zementzusammensetzung nach Anspruch 6, ferner umfassend Hydroxypropylmethacrylat, HPMA.
     
    9. Zweiteilige harzverstärkte temporäre Zementzusammensetzung nach Anspruch 1, ferner umfassend Wasser.
     
    10. Zweiteilige harzverstärkte temporäre Zementzusammensetzung nach Anspruch 1, ferner umfassend mindestens ein Färbemittel.
     
    11. Zweiteilige harzverstärkte temporäre Zementzusammensetzung nach Anspruch 1, wobei es sich bei dem aliphatischen Kohlenwasserstoff um Polybutadien handelt.
     
    12. Zweiteilige harzverstärkte temporäre Zementzusammensetzung nach Anspruch 3, wobei der Weichmacher und der nicht reaktive Füllstoff zusammen mindestens 35 Prozent bezogen auf das Gewicht der Zusammensetzung umfassen.
     
    13. Zweiteilige harzverstärkte temporäre Zementzusammensetzung nach Anspruch 3, wobei der nicht reaktive Füllstoff zwischen 3 Prozent und 30 Prozent bezogen auf das Gewicht der Zusammensetzung umfasst.
     
    14. Zweiteilige harzverstärkte temporäre Zementzusammensetzung nach Anspruch 1, wobei der temporäre Zement eine Druckfestigkeit aufweist, die nicht größer als 70 MPa ist, gemessen durch das folgende Verfahren:
    Die gemischte zweiteilige Zusammensetzung wird in eine zylindrische Form gegeben und man lässt sie aushärten. Nach dem Aushärten wurde die Probe aus der Form entfernt und mit Schmirgelpapier geschmirgelt, um den Zylinder zu einem Zylinder zu reduzieren, der Ausmaße von 2,15 mm Höhe und 2,35 mm Durchmesser aufweist. Ein INSTRON-Gerät zur Messung der Druckfestigkeit wird verwendet, um die Probe zu zerbrechen, um so die Druckfestigkeit zu testen.
     
    15. Zweiteilige harzverstärkte temporäre Zementzusammensetzung nach Anspruch 1, wobei der temporäre Zement eine Haftfestigkeit aufweist, die nicht größer als 2,5 MPa ist, wobei die Haftfestigkeit durch Ausführen eines simulierten "Kronenziehungs"-Tests an einem konisch geformten menschlichen Zahn ausgeführt wird, auf welchen eine simulierte Metall-"Krone" unter Verwendung der temporären Zementzusammensetzung zementiert wird, wobei ein INSTRON-Gerät verwendet wird, um die Krone vom Zahn abzuziehen, um so die Haftfestigkeit zu testen.
     
    16. Kit zum temporären Befestigen einer provisorischen Zahnprothesevorrichtung an einem Zahn, umfassend:

    eine zweiteilige harzverstärkte temporäre Zementzusammensetzung wie in einem der Ansprüche 1 bis 15 aufgeführt; und

    eine provisorische Zahnprothesevorrichtung.


     


    Revendications

    1. Composition en deux parties de ciment temporaire renforcé de résine pour la liaison de manière temporaire d'un appareil prothétique dentaire provisoire à une dent comprenant :

    une première partie comprenant un composant activateur amine et de l'oxyde de zinc ; et

    une seconde partie comprenant un initiateur de polymérisation qui est déstabilisé lorsqu'il est mélangé avec le composant activateur amine, la seconde partie comprenant en outre un composant polymérisable ayant une structure incluant au moins l'un d'un groupe acrylate ou méthacrylate à une extrémité et d'un groupe acide carboxylique à une autre extrémité, la seconde partie étant initialement séparée de la première partie,

    où au moins l'un de la première ou de la seconde partie comprend en outre un agent plastifiant sélectionné parmi la glycérine, un ester de méthyle hydrogéné de colophane, de l'alcool de cétyle, un polysorbate, et/ou un hydrocarbure aliphatique en une quantité de 15 % à 70 % en poids de la composition de ciment temporaire afin de réduire la force de liaison du ciment temporaire à une valeur non supérieure à 3 MPa, ladite force de liaison étant mesurée en effectuant un test de « traction en couronne » simulée sur une dent humaine de forme conique sur laquelle une « couronne » métallique simulée est cimentée en utilisant la composition de ciment temporaire, un dispositif INSTRON étant utilisé pour extraire la couronne de la dent afin de tester la force de liaison.


     
    2. Composition en deux parties de ciment temporaire renforcé de résine selon la revendication 1, l'oxyde de zinc comprenant entre 3 pour cent et 50 pour cent en poids de la composition.
     
    3. Composition en deux parties de ciment temporaire renforcé de résine selon la revendication 1, comprenant en outre une charge non réactive.
     
    4. Composition en deux parties de ciment temporaire renforcé de résine selon la revendication 1, le composant polymérisable ayant une structure incluant au moins l'un d'un groupe acrylate ou méthacrylate à une extrémité et d'un groupe acide carboxylique à une autre extrémité comprenant du succinate de mono-2-(méthacryloyloxy)éthyle et/ou du méthacrylate de 2-hydroxyéthyle/anhydride phtalique ayant la structure


     
    5. Composition en deux parties de ciment temporaire renforcé de résine selon la revendication 1, comprenant en outre au moins un composant polymérisable de réticulation.
     
    6. Ciment temporaire renforcé de résine en deux parties selon la revendication 5, le composant polymérisable de réticulation comprenant au moins un élément sélectionné dans le groupe constitué du méthacrylate glycidylique de bisphénol-A, Bis-GMA ; du diméthacrylate de diuréthane, DUDMA ; du diméthacrylate de triéthylène glycol, TEGDMA ; du méthacrylate d'hydroxyéthyle, HEMA ; et du diméthacrylate de glycérol, GDMA.
     
    7. Composition en deux parties de ciment temporaire renforcé de résine selon la revendication 5, au moins l'un des composants polymérisables de réticulation étant phosphaté.
     
    8. Composition en deux parties de ciment temporaire renforcé de résine selon la revendication 6, comprenant en outre du méthylacrylate d'hydroxypropyle, HPMA.
     
    9. Composition en deux parties de ciment temporaire renforcé de résine selon la revendication 1, comprenant en outre de l'eau.
     
    10. Composition en deux parties de ciment temporaire renforcé de résine selon la revendication 1, comprenant en outre au moins un colorant.
     
    11. Composition en deux parties de ciment temporaire renforcé de résine selon la revendication 1, l'hydrocarbure aliphatique étant le polybutadiène.
     
    12. Composition en deux parties de ciment temporaire renforcé de résine selon la revendication 3, l'agent plastifiant et la charge non réactive comprenant de manière collective au moins 35 pour cent en poids de la composition.
     
    13. Composition en deux parties de ciment temporaire renforcé de résine selon la revendication 3, la charge non réactive comprenant entre 3 pour cent et 30 pour cent en poids de la composition.
     
    14. Composition en deux parties de ciment temporaire renforcé de résine selon la revendication 1, le ciment temporaire ayant une force de compression qui n'est pas supérieure à 70 MPa mesurée selon le procédé suivant :
    la composition mixte en deux parties est placée dans un moule cylindrique et laissée à durcir. Après le durcissement, on a retiré l'échantillon du moule et poncé avec du papier de verre pour réduire le cylindre jusqu'à un cylindre ayant les dimensions de 2,15 mm de hauteur et de 2,35 mm de diamètre. On a utilisé un dispositif INSTRON de mesure de la force de compression pour écraser l'échantillon afin de tester la force de compression.
     
    15. Composition en deux parties de ciment temporaire renforcé de résine selon la revendication 1, le ciment temporaire ayant une force de liaison qui n'est pas supérieure à 2,5 MPa, ladite force de liaison étant mesurée en effectuant un test de « traction en couronne » simulée sur une dent humaine de forme conique sur laquelle une « couronne » métallique simulée est cimentée en utilisant la composition de ciment temporaire, un dispositif INSTRON étant utilisé pour extraire la couronne de la dent afin de tester la force de liaison.
     
    16. Kit de liaison temporaire d'un appareil prothétique dentaire provisoire à une dent comprenant :

    une composition en deux parties de ciment temporaire renforcé de résine telle qu'énoncée selon l'une quelconque des revendications 1 à 15 ; et

    un appareil prothétique dentaire provisoire.


     




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    Cited references

    REFERENCES CITED IN THE DESCRIPTION



    This list of references cited by the applicant is for the reader's convenience only. It does not form part of the European patent document. Even though great care has been taken in compiling the references, errors or omissions cannot be excluded and the EPO disclaims all liability in this regard.

    Patent documents cited in the description