Dental Composition

Abstract

A dental composition comprising one or more di- or polyepoxides; and (ii) a compound of formula (I): TIFF2022529600000020.tif74161

Description

[Technical Field]

[0001] The present invention relates to dental compositions containing specific primary amine compounds. The dental compositions of the present invention are adapted to form epoxide-amine addition polymers. Furthermore, the present invention relates to specific primary amine compounds for use in the treatment or prevention of endodontic disease. [Background technology]

[0002] Polymerizable dental compositions containing polymerizable compounds are known. Conventionally, polymerizable dental compositions have been provided for a wide range of applications and therefore must meet a variety of requirements. For example, the polymerizable dental composition can be a dental adhesive composition, a bonding agent, a pit and fissure sealant, a dental desensitizing composition, a pulp-capping composition, a dental composite, a dental glass ionomer cement, a dental cement, a dental root canal filling sealer composition, a root canal filling composition, or a dental infiltrant.

[0003] It is desirable for dental compositions to approximate the structure of natural teeth in terms of strength and appearance. Accordingly, the prior art has documented considerable efforts directed toward developing dental compositions with improved properties in terms of physical properties, biocompatibility, aesthetics, and handling.

[0004] U.S. Pat. No. 5,624,976 discloses a dental filling composition for sealing root canals, in which aniline, p-fluoroaniline, benzylamine, 1-aminoadamantane, α-phenylethylamine, dimethyl(amino)methyl)phosphine oxide and ethanolamine can be used as monoamine compounds.

[0005] Dental compositions selected from root canal filling compositions and pulp capping compositions are required to have high radiopacity in the hardened product, with the additional requirement that the composition does not require external irradiation for hardening. Moreover, it is desirable for the composition to adhere to the root canal wall to further improve the sealing of the root canal. Given that the shape of the root canal can change as a result of mastication and temperature changes, the hardened composition must tolerate such changes without compromising the sealing of the root canal.

[0006] Therefore, to provide such additional properties, root canal filling or pulp capping compositions contain radiopaque particulate fillers dispersed in a hardenable matrix. However, dispersion of radiopaque particulate fillers creates stability problems for the dispersion due to the high density of the filler and the low viscosity of the hardenable matrix.

[0007] Moreover, to harden the root canal filling or pulp capping composition in the absence of light, the composition is hardened by a thermal curing mechanism which may involve the step-growth polymerization of epoxide precursor compounds.

[0008] Prior art dental filling materials for root canals have relatively long setting times, high viscosity and discoloration.

[0009] Currently, the gold standard for dental root canal filling materials offering the best overall properties is AH Plus® (Dentsply DeTrey, Konstanz / Germany). The good overall properties of AH Plus® relate in particular to physical and mechanical properties, setting characteristics such as gel time, and handling properties such as flowability and viscosity. The good overall properties depend largely on the filling material composition used and the structure of the epoxide-amine addition polymer that forms during the setting process of the AH Plus® composition. The AH Plus® dental root canal filling composition consists of an amine paste and an epoxide paste. AH Plus® Epoxide Paste contains bisphenol A diglycidyl ether (EP, CAS: 25068-38-6) as its main component, and AH Plus® Amine Paste contains the diamine N,N'-dibenzyl-5-oxanonanediamine-1,9 (DA, CAS: 113506-22-2) and the monoamine 1-aminomonoadamantane (MA, CAS: 768-94-5) as its main components. The molecular structures of these three main components of AH Plus® are shown below.

[0010] [ka]

[0011] As can be seen from the above structure, the three main components of the AH Plus® composition—EP, DA, and MA—have mirror-symmetric molecular structures. In particular, the monoamine 1-aminoadamantane (MA) possesses a very high level of symmetry. Due to the fact that the addition polymerization process is a statistical polymerization process and that the monomers used in AH Plus® are primarily mirror-symmetric monomers, a large number of mirror-symmetric subunits form in the polymer structure during the polymerization process. These mirror-symmetric subunits have a significant effect on the properties of the resulting polymer. Aside from various diastereoisomers, the smallest possible mirror-symmetric subunits of the polymer are shown below; however, larger mirror-symmetric subunits in the polymer that form during curing of AH Plus® are also possible but are not shown. Generally, however, eight mirror-symmetric subunits are possible.

[0012] [ka]

[0013] The monomers EP, DA, and MA used in AH Plus® are relatively large monomers, and therefore the mirror-symmetric subunits constitute relatively large blocks of the final polymer. For this reason, the mirror-symmetric subunits have a significant effect on the physical and mechanical properties of the final polymer; in particular, viscosity and flowability depend on the mirror-symmetric subunits. As a result, the mirror-symmetric subunits contribute significantly to the overall properties of AH Plus. Summary of the Invention [Problem to be solved by the invention]

[0014] The object of the present invention is to provide a dental composition having excellent properties in terms of physical and mechanical properties, biocompatibility, aesthetics and ease of handling.

[0015] It is a further object of the present invention to provide a dental composition that has high radiopacity, high storage stability, low shrinkage and flexibility, a relatively short curing time, and can be cured in the absence of light.

[0016] Furthermore, it is an object of the present invention to provide a dental composition which has adjustable application and hardening times, suitable viscosity and does not exhibit discoloration problems.

[0017] It is a further object of the present invention to provide hardenable dental compositions selected from root canal filling and pulp capping compositions that are cost-effective, simple and available on an industrially relevant scale.

[0018] It is a further object of the present invention to provide dental compositions having comparable and / or improved overall properties compared to AH Plus® compositions. [Means for solving the problem]

[0019] Surprisingly, the object of the present invention is to (i) one or more di- or polyepoxides; (ii) a compound represented by the following formula (I):

[0020] [ka]

[0021] (In the formula, L is one or more fluorine atoms, hydroxyl groups, C 1-6 Alkoxy group, C 1-6 Alkylthio group, C 6-10 Aryl group, C 6-10 Aryloxy group, C 7-14 Aryl alkyl group or C 7-14 a linear or branched hydrocarbon group having 1 to 8 carbon atoms, optionally substituted by an arylalkoxy group; A 1 , A 2 and A 3At least one of the groups represents CH, and the remaining groups represent CR groups. 1 and; X 1 , X 2 , X 3 , Y 1 , Y 2 and Y 3 At least three of the groups represent CH2, and the remaining groups are CHR 2 group, CR 3 R 4 group or C=NR 5 It is a base; n is 0 or 1; R 1 is a fluorine atom, a hydroxyl group, an amino group, C 1-6 Alkyl group, C 1-6 Alkoxy group, C 1-6 Alkylthio group, C 6-10 Aryl group, C 6-10 Aryloxy group, C 7-14 Aryl alkyl group or C 7-14 is an arylalkoxy group; R 2 is a fluorine atom, a hydroxyl group, an amino group, C 1-6 Alkyl group, C 1-6 Alkoxy group, C 1-6 Alkylthio group, C 6-10 Aryl group, C 6-10 Aryloxy group, C 7-14 Aryl alkyl group or C 7-14 is an arylalkoxy group; R 3 and R 4 may be the same or different and independently represent a fluorine atom, C 1-6 Alkyl group, C 1-6 Alkoxy group, C 1-6 Alkylthio group, C 6-10 Aryl group, C 6-10 Aryloxy group, C 7-14 Aryl alkyl group or C 7-14 represents an arylalkoxy group, or R 3 and R 4 and may be joined together with the carbon atom to which they are attached to form a 3- to 6-membered saturated hydrocarbon ring; R5 is a hydroxyl group, an amino group, C 1-6 Alkyl group, C 1-6 Alkoxy group, C 6-10 Aryl group, C 6-10 Aryloxy group, C 7-14 Aryl alkyl group or C 7-14 is an arylalkoxy group; However, when n is 0, R 1 , R 2 , R 3 / R 4 and R 5 (At least one of Compounds of It has been found that the above-mentioned problems can be solved by the dental composition of the present invention, which comprises:

[0022] It has been surprisingly found that the use of an asymmetric primary amine monomer of formula (I) can provide dental compositions with comparable and / or improved overall properties compared to AH Plus® compositions. The use of an asymmetric primary amine monomer of formula (I) reduces the number of possible mirror-symmetric subunits from 8 to 3, thus reducing the number of mirror-symmetric subunits statistically forming in the final polymer by 62.5%. It has thus been surprisingly found that a 62.5% reduction in mirror-symmetric subunits in the final polymer of a hardened dental composition (which has a significant impact on the overall properties of the polymer) results in dental compositions with comparable and / or improved overall properties compared to AH Plus® compositions.

[0023] Additionally, the present invention provides a dental composition further comprising a radiopaque particulate filler.

[0024] Additionally, the present invention provides dental compositions that are root canal filling compositions or pulp capping compositions.

[0025] Additionally, the present invention provides dental compositions having a gel time of at most 20 hours.

[0026] Finally, the present invention relates to a compound of formula (I) below for use in the treatment or prevention of endodontic diseases:

[0027] [ka]

[0028] (In the formula, L is one or more fluorine atoms, hydroxyl groups, C 1-6 Alkoxy group, C 1-6 Alkylthio group, C 6-10 Aryl group, C 6-10 Aryloxy group, C 7-14 Aryl alkyl group or C 7-14 a linear or branched hydrocarbon group having 1 to 8 carbon atoms, optionally substituted by an arylalkoxy group; A 1 , A 2 and A 3 At least one of the groups represents CH, and the remaining groups represent CR groups. 1 and; X 1 , X 2 , X 3 , Y 1 , Y 2 and Y 3 At least three of the groups represent CH2, and the remaining groups are CHR 2 group, CR 3 R 4 group or C=NR 5 It is a base; n is 0 or 1; R 1 is a fluorine atom, a hydroxyl group, an amino group, C 1-6 Alkyl group, C 1-6 Alkoxy group, C 1-6 Alkylthio group, C 6-10 Aryl group, C 6-10 Aryloxy group, C 7-14 Aryl alkyl group or C 7-14 is an arylalkoxy group; R 2 is a fluorine atom, a hydroxyl group, an amino group, C 1-6 Alkyl group, C1-6 Alkoxy group, C 1-6 Alkylthio group, C 6-10 Aryl group, C 6-10 Aryloxy group, C 7-14 Aryl alkyl group or C 7-14 is an arylalkoxy group; R 3 and R 4 may be the same or different and independently represent a fluorine atom, C 1-6 Alkyl group, C 1-6 Alkoxy group, C 1-6 Alkylthio group, C 6-10 Aryl group, C 6-10 Aryloxy group, C 7-14 Aryl alkyl group or C 7-14 represents an arylalkoxy group, or R 3 and R 4 and may be joined together with the carbon atoms to which they are attached to form a 3- to 6-membered saturated hydrocarbon ring; R 5 is a hydroxyl group, an amino group, C 1-6 Alkyl group, C 1-6 Alkoxy group, C 6-10 Aryl group, C 6-10 Aryloxy group, C 7-14 Aryl alkyl group or C 7-14 is an arylalkoxy group; However, when n is 0, R 1 , R 2 , R 3 / R 4 and R 5 (At least one of The present invention provides a compound of the formula:

[0029] The present invention is based on the recognition that dental compositions containing a compound of formula (I) provide dental compositions with comparable and / or improved overall properties compared to AH Plus® compositions. Furthermore, the present invention is based on the recognition that dental compositions containing a compound of formula (I) provide dental compositions with superior properties in terms of physical and mechanical properties, biocompatibility, aesthetics, and handling, high radiopacity, high storage stability, low shrinkage and flexibility, a relatively short hardening time, and the ability to harden in the absence of light. Furthermore, the dental compositions of the present invention provide adjustable lamination and hardening times, suitable viscosity, and no discoloration problems. Finally, the present invention provides hardenable dental compositions selected from root canal filling compositions and pulp-capping compositions that are cost-effective, simple, and available on an industrially relevant scale.

[0030] The primary monoamine monomers of formula (I) of the present invention are adapted to serve as monomers that provide superior reactivity, resulting in dental compositions with superior hardening properties. Furthermore, the use of the primary monomers of formula (I) of the present invention results in polymers with a reduced number of mirror-symmetric subunits and comparable and / or improved overall properties compared to the final polymers of AH Plus® compositions. [Brief explanation of the drawings]

[0031] [Figure 1] 1 shows a summary of experimental results that are further disclosed in the Examples. DETAILED DESCRIPTION OF THE INVENTION

[0032] Detailed Description of the Preferred Embodiments The present invention relates to a dental composition containing a specific primary amine compound. The dental composition of the present invention is adapted to form an epoxide-amine addition polymer. The dental composition contains a di- or polyepoxide and a primary monoamine of formula (I) and / or other monoamines and / or secondary diamines and / or fillers. The dental composition of the present invention is polymerizable and forms a thermoplastic polymer upon polymerization.

[0033] Furthermore, the present invention relates to certain primary amine compounds for use in the treatment or prevention of endodontic disease.

[0034] The terms "polymerization" and "polymerizable" refer to the covalent combination of a large number of smaller molecules, e.g., monomers, to form a larger molecule, i.e., a macromolecule or polymer. Monomers can combine to form solely linear macromolecules, or they can combine to form three-dimensional macromolecules, commonly referred to as cross-linked polymers. For example, difunctional monomers form linear polymers, while monomers with at least three functional groups form cross-linked polymers, also known as networks. Higher conversion of polymerizable monomers can reduce the amount of multifunctional monomers and alleviate leaching problems.

[0035] The term "curing" refers to the polymerization of functional polymerizable compounds, such as monomers, oligomers, or even polymers, into a polymer network, preferably a crosslinked polymer network.

[0036] The term "hardenable" means that the dental composition polymerizes upon mixing.

[0037] "Working time" is the time measured between the initiation of the setting reaction when the polymer and modified particulate reactive filler are combined in the presence of water and the point at which the setting reaction has progressed to the point where further physical manipulation, such as spatulation or reshaping, for the intended dental or medical use can no longer be performed on the system.

[0038] "Setting time" is the time measured from the initiation of the setting reaction in the filled area to the point at which sufficient hardening has occurred to allow subsequent clinical or surgical treatment of the surface of the filled area. During the setting reaction, a polymerization reaction occurs due to the presence of polymerizable groups. In glass ionomer cements, in addition to the polymerization reaction, the setting reaction also involves the neutralization of, for example, acid groups of the polymerizable compound by a base in the form of a reactive particulate glass.

[0039] As used herein, the term "storage stable" means that the dental composition maintains its properties, particularly its application and setting times, even after extended storage periods, for example, about two years.

[0040] Compounds of formula (I) The dental composition of the present invention has the following formula (I):

[0041] [ka]

[0042] (In the formula, L is one or more fluorine atoms, hydroxyl groups, C 1-6 Alkoxy group, C 1-6 Alkylthio group, C 6-10 Aryl group, C 6-10 Aryloxy group, C 7-14 Aryl alkyl group or C 7-14 a linear or branched hydrocarbon group having 1 to 8 carbon atoms, optionally substituted by an arylalkoxy group; A 1 , A 2 and A 3 At least one of the groups represents CH, and the remaining groups represent CR groups. 1 and; X 1 , X 2 , X 3 , Y 1 , Y 2 and Y 3 At least three of the groups represent CH, and the remaining groups are CHR2 , C.R. 3 R 4 or C=NR 5 and; n is 0 or 1; R 1 is a fluorine atom, a hydroxyl group, an amino group, C 1-6 Alkyl group, C 1-6 Alkoxy group, C 1-6 Alkylthio group, C 6-10 Aryl group, C 6-10 Aryloxy group, C 7-14 Aryl alkyl group or C 7-14 is an arylalkoxy group; R 2 is a fluorine atom, a hydroxyl group, an amino group, C 1-6 Alkyl group, C 1-6 Alkoxy group, C 1-6 Alkylthio group, C 6-10 Aryl group, C 6-10 Aryloxy group, C 7-14 Aryl alkyl group or C 7-14 is an arylalkoxy group; R 3 and R 4 may be the same or different and independently represent a fluorine atom, C 1-6 Alkyl group, C 1-6 Alkoxy group, C 1-6 Alkylthio group, C 6-10 Aryl group, C 6-10 Aryloxy group, C 7-14 Aryl alkyl group or C 7-14 represents an arylalkoxy group, or R 3 and R 4 and may be joined together with the carbon atoms to which they are attached to form a 3- to 6-membered saturated hydrocarbon ring; R 5 is a hydroxyl group, an amino group, C 1-6 Alkyl group, C 1-6 Alkoxy group, C 6-10 Aryl group, C 6-10 Aryloxy group, C 7-14 Aryl alkyl group or C 7-14 is an arylalkoxy group; However, when n is 0, R 1 , R 2 , R 3 / R 4 and R 5 (At least one of This includes compounds of the formula:

[0043] In the compounds of formula (I), L is one or more fluorine atoms, hydroxyl groups, C 1-6 Alkoxy group, C 1-6 Alkylthio group, C 6-10 Aryl group, C 6-10 Aryloxy group, C 7-14 Aryl alkyl group or C 7-14 L represents a linear or branched hydrocarbon group having 1 to 8 carbon atoms, which may be substituted with an arylalkoxy group. Preferably, L represents a linear hydrocarbon group having 1 to 8 carbon atoms, more preferably, L represents a linear hydrocarbon group having 2 to 6 carbon atoms, even more preferably, L represents a linear hydrocarbon group having 2 to 4 carbon atoms, and most preferably, L represents a linear hydrocarbon group having 2 carbon atoms.

[0044] L is one or more fluorine atoms, hydroxyl groups, C 1-6 Alkoxy group, C 1-6 Alkylthio group, C 6-10 Aryl group, C 6-10 Aryloxy group, C 7-14 Aryl alkyl group or C 7-14 L may be substituted by an arylalkoxy group. Preferably, L is substituted by one or more fluorine atoms, hydroxyl groups, or is unsubstituted, more preferably, L is substituted by one or more hydroxyl groups, or is unsubstituted, and even more preferably, L is unsubstituted.

[0045] In a particularly preferred embodiment, L represents the following group:

[0046] [ka]

[0047] In the compound of formula (I), A 1 , A 2 and A 3 At least one of the groups represents CH, and the remaining groups represent CR groups. 1 Preferably, A 1 , A 2 and A 3 At least two or three of the groups represent CH, and the remaining groups are groups CR 1 and more preferably, A 1 , A 2 and A 3 At least three of these represent CH.

[0048] In the compound of formula (I), X 1 , X 2 , X 3 , Y 1 , Y 2 and Y 3 At least three of the groups represent CH, and the remaining groups are CHR 2 , C.R. 3 R 4 or C=NR 5 Preferably, X 1 , X 2 , X 3 , Y 1 , Y 2 and Y 3 At least four of the groups represent CH, and the remaining groups are CHR 2 , C.R. 3 R 4 or C=NR 5 and more preferably, X 1 , X 2 , X 3 , Y 1 , Y 2 and Y 3 At least five of the groups represent CH, and the remaining groups are CHR 2 , C.R. 3 R 4 or C=NR 5 and most preferably X 1 , X 2 , X 3 , Y 1 , Y2 and Y 3 At least six of these represent CH2.

[0049] Preferably, X 1 , X 2 , X 3 , Y 1 , Y 2 and Y 3 at least three, or at least four, or at least five of the groups represent CH, and the remaining groups are CHR 2 , C.R. 3 R 4 and more preferably the remaining groups are CHR 2 It is based on.

[0050] In a preferred embodiment, the compound of formula (I) is A 1 , A 2 and A 3 represents CH, and X 1 , X 2 , X 3 , Y 1 , Y 2 and Y 3 is a compound that represents CH2.

[0051] In the compounds of formula (I), n is 0 or 1. Preferably, n is 1. However, in one embodiment, the compounds of formula (I) are those in which n is 0. If n is 0, then R 1 , R 2 , R 3 / R 4 and R 5 At least one of the following is present.

[0052] In the compounds of formula (I), R 1 is a fluorine atom, a hydroxyl group, an amino group, C 1-6 Alkyl group, C 1-6 Alkoxy group, C 1-6 Alkylthio group, C 6-10 Aryl group, C 6-10 Aryloxy group, C 7-14 Aryl alkyl group or C 7-14 An arylalkoxy group. Preferably, R 1is a fluorine atom, a hydroxyl group, an amino group, C 1-6 Alkyl group, C 1-6 is an alkoxy group, and more preferably, R 1 is a fluorine atom, a hydroxyl group, an amino group, C 1-6 alkyl group, and more preferably R 1 is a fluorine atom, a hydroxyl group, C 1-6 alkyl groups, in particular R 1 is a hydroxyl group.

[0053] In the compounds of formula (I), R 2 is a fluorine atom, a hydroxyl group, an amino group, C 1-6 Alkyl group, C 1-6 Alkoxy group, C 1-6 Alkylthio group, C 6-10 Aryl group, C 6-10 Aryloxy group, C 7-14 Aryl alkyl group or C 7-14 An arylalkoxy group. Preferably, R 2 is a fluorine atom, a hydroxyl group, an amino group, C 1-6 Alkyl group, C 1-6 is an alkoxy group, and more preferably, R 2 is a fluorine atom, a hydroxyl group, an amino group, C 1-6 alkyl group, and more preferably R 2 is a fluorine atom, a hydroxyl group, C 1-6 alkyl groups, in particular R 2 is a hydroxyl group.

[0054] In the compounds of formula (I), R 3 and R 4 may be the same or different and independently represent a fluorine atom, C 1-6 Alkyl group, C 1-6 Alkoxy group, C 1-6 Alkylthio group, C 6-10 Aryl group, C 6-10 Aryloxy group, C 7-14 Aryl alkyl group or C 7-14 represents an arylalkoxy group, or R 3and R 4 may be linked together with the carbon atom to which they are attached to form a 3- to 6-membered saturated hydrocarbon ring.

[0055] In the compounds of formula (I), R 5 is a hydroxyl group, an amino group, C 1-6 Alkyl group, C 1-6 Alkoxy group, C 6-10 Aryl group, C 6-10 Aryloxy group, C 7-14 Aryl alkyl group or C 7-14 It represents an arylalkoxy group. Preferably, R 5 is C 1-6 Alkyl group, C 6-10 Aryl group or C 7-14 represents an arylalkyl group, and more preferably, R 5 is C 1-6 Alkyl group or C 6-10 represents an aryl group, and more preferably R 5 is C 1-6 represents an alkyl group.

[0056] In a particularly preferred embodiment, the compound of formula (I) is:

[0057] [ka]

[0058] One or more di- or polyepoxides The dental compositions of the present invention include one or more di- or polyepoxides. The one or more di- or polyepoxides can be any di- or polyepoxide suitable for dental use and / or known in the art.

[0059] In a specific embodiment, the one or more di- or polyepoxides have the following formula (II):

[0060] [ka]

[0061] (In the formula, Q is an (m+1)-valent organic group, R 6 , R 7 and R 10 may be the same or different and independently represent a hydrogen atom or C 1-6 represents an alkyl group, R 8 , R 9 and R 11 may be the same or different and independently represent a hydrogen atom or C 1-6 represents an alkyl group, m is an integer from 1 to 3. is a compound of

[0062] In the compound of formula (II), Q represents an (m+1)-valent organic group. Preferably, Q represents a divalent organic group or a trivalent organic group, and more preferably, Q represents a divalent organic group.

[0063] The (m+1)-valent organic group can be a group having a total of 1 to 40 carbon atoms, preferably 2 to 20 carbon atoms. The organic group can contain an aliphatic, alicyclic, or aromatic moiety, or a combination of two or more of such moieties. The organic group may further contain one or more functional groups connecting two or more aliphatic, alicyclic, or aromatic moieties, such as an amide group, an ester group, a urethane group, a urea group, a keto group, an ether group, a thioether group, a carbonate group, or a tertiary amino group. Additionally, the organic group may contain a hydroxyl group, a halogen atom, a C 1-6 Alkyl group, C 1-6 Alkoxy group, C 1-6 Alkylthio group, C 6-10 Aryl group, C 6-10 Aryloxy group, C 7-14 Aryl alkyl group or C 7-14 It may be substituted with one or more substituents selected from arylalkoxy groups.

[0064] Preferably, the (m+1)-valent organic group can include an alicyclic or aromatic moiety, and more preferably, the (m+1)-valent organic group can include an aromatic moiety.

[0065] In a preferred embodiment, Q represents the following group:

[0066] [ka]

[0067] In the compound of formula (III), m is an integer of 1 to 3. Preferably, m is an integer of 1 to 2, and more preferably, m is 1.

[0068] In the compound of formula (II), R 6 , R 7 and R 10 may be the same or different and independently represent a hydrogen atom or C 1-6 It represents an alkyl group. Preferably, R 6 , R 7 and R 10 represents a hydrogen atom. In a particularly preferred embodiment, R 6 , R 7 and R 10 All three represent hydrogen atoms.

[0069] In the compound of formula (II), R 8 , R 9 and R 11 may be the same or different and independently represent a hydrogen atom or C 1-6 Furthermore, in compounds of formula (II), more than one R 8 If there is more than one R 8 In compounds of formula (II), more than one R 9 If there is more than one R 9 In compounds of formula (II), more than one R 11 If there is more than one R 11 may be different. Preferably, R8 , R 9 and R 11 represents a hydrogen atom. In a particularly preferred embodiment, the R 8 , R 9 and R 11 All of the parts are hydrogen atoms.

[0070] In a particularly preferred embodiment, the compound of formula (II) is bisphenol A diglycidyl ether (CAS: 25068-38-6) or bis-[4-(2,3-epoxypropoxy)phenyl]-methane (CAS: 9003-36-5).

[0071] Further ingredients Aliphatic Polyamines The dental compositions of the present invention may further comprise an aliphatic polyamine, which can be any aliphatic polyamine suitable for dental use and / or known in the art.

[0072] In a specific embodiment, the aliphatic polyamine has the following structure:

[0073] [ka]

[0074] (In the formula, R 12 is hydrogen or substituted or unsubstituted C 1-18 Alkyl groups, substituted or unsubstituted C 3-18 Cycloalkyl group or substituted or unsubstituted C 7-18 is an arylalkyl group, R 13 is a bifunctional substituted or unsubstituted C1-C 18 an alkylene group or a substituted or unsubstituted cycloalkylene group; A' is a moiety derived from a compound capable of addition reaction with an amine, such as a di- or polyepoxide; c is an integer) The compound is selected from the group consisting of:

[0075] In the aliphatic polyamine of the above structure, preferably, R 12 is hydrogen, substituted or unsubstituted C 3-18 Cycloalkyl group or C 7-18 More preferably, R 12 is a substituted or unsubstituted C 3-18 Cycloalkyl group or substituted or unsubstituted C 7-18 It is preferably an arylalkyl group. 12 is a substituted or unsubstituted C 7-18 In a particularly preferred embodiment, R 12 is unsubstituted C 7-18 It is an arylalkyl group.

[0076] In the aliphatic polyamine of the above structure, preferably, R 13 is a bifunctional substituted or unsubstituted C1-C 18 is an alkylene group, and more preferably, R 13 is a bifunctional unsubstituted C1-C 18 It is an alkylene group.

[0077] In the aliphatic polyamine of the above structure, A' is a moiety derived from a compound capable of addition reacting with an amine, such as a di- or polyepoxide. Preferably, A' is a moiety derived from the addition reaction of a di- or polyepoxide of formula (II) with an amine. More preferably, A' is a moiety derived from the addition reaction of an amine with a compound of formula (II) that is a diepoxide.

[0078] In a preferred embodiment, A' is a moiety derived from the addition reaction of an amine with a compound of formula (II) that is a diepoxide, and in the compound of formula (II), Q represents the following structure:

[0079] [ka]

[0080] In the aliphatic polyamine having the above structure, c is an integer. Preferably, c is an integer of 1 to 10, more preferably c is an integer of 2 to 8, and even more preferably c is an integer of 4 to 6.

[0081] filling material The dental composition of the present invention may further comprise a filler. The filler in the dental composition of the present invention can be any filler suitable for dental use and / or known in the art.

[0082] In a specific embodiment, the filler of the present invention is a radiopaque particulate filler. The radiopaque filler of the present invention can be any radiopaque filler suitable for dental applications and / or known in the art.

[0083] Radiopaque fillers typically have an average particle size of 0.005 to 100 μm, preferably 0.01 to 40 μm, as measured, for example, by using an electron microscope or conventional laser diffraction particle size measurement techniques such as those embodied by a MALVERN Mastersizer S or MALVERN Mastersizer 2000 instrument. The radiopaque particulate filler may also be a multimodal radiopaque particulate filler, representing a mixture of two or more radiopaque particulate fractions having different average particle sizes. The radiopaque particulate filler may also be a mixture of particles of different chemical compositions.

[0084] The radiopaque filler in the form of a particulate filler or nanofiller can be selected from any of the following metals, alloys, organometallic complexes, oxides, sulfates, carbonates, halides, oxyhalides, subnitrates, tungstates, and carbides: zinc, ytterbium, yttrium, gadolinium, zirconium, strontium, tungsten, tantalum, thorium, niobium, barium, bismuth, molybdenum, and lanthanum, iodine, and inorganic iodides, alone or in combination. In a preferred embodiment, the radiopaque filler is selected from any of the following: bismuth trioxide, bismuth carbonate, bismuth oxide chloride, bismuth subnitrate, zirconium oxide, barium sulfate, barium tungstate, and calcium tungstate, alone or in combination. In a more preferred embodiment, the radiopaque filler is selected from barium tungstate and calcium tungstate, alone or in combination. Preferably, the radiopaque filler is calcium tungstate.

[0085] The dental composition of the present invention preferably contains 1 to 85 wt %, more preferably 40 to 85 wt %, and even more preferably 40 to 70 wt % of the radiopaque particulate filler based on the weight of the entire composition.

[0086] The viscosity and thixotropy of the uncured composition and the physical properties of the cured composition can be controlled by varying the size and surface area of ​​the filler.

[0087] The filler may be surface-treated with one or more silanizing agents. Preferred silanizing agents include those having at least one polymerizable double bond and at least one group that readily hydrolyzes with water. Examples of such silanizing agents include 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropyldimethoxymonochlorosilane, 3-methacryloxypropyldichloromonomethoxysilane, methacryloxypropyltrichlorosilane, 3-methacryloxypropyldichloromonomethylsilane, 3-methacryloxypropylmonochlorodimethylsilane, or 2,3-epoxypropyltrimethoxysilane, aminopropyltrimethoxysilane, mercaptopropyltrimethoxysilane, and mixtures thereof.

[0088] Aliphatic mono- and diamines The dental composition of the present invention may further comprise an aliphatic mono- and / or diamine, which can be any aliphatic mono- and / or diamine suitable for dental applications and / or known in the art.

[0089] In a preferred embodiment, the dental composition of the present invention comprises a monoamine selected from the group consisting of benzylamine, 1-aminoadamantane, α-phenylethylamine, dimethyl(aminomethyl)phosphine oxide, and ethanolamine.

[0090] In a preferred embodiment, the dental composition of the present invention comprises a diamine selected from the group consisting of N,N'-dibenzylethylenediamine, N,N'-dibenzyl-3,6-dioxaoctanediamine-1,8, N,N'-dibenzyl-5-oxanonanediamine-1,9 (CAS: 113506-22-2), N,N'-dibenzyl-(2,2,4)trimethylhexamethylenediamine, N,N'-dibenzyl-(2,2,4)trimethylhexamethylenediamine, N,N'-dibenzylcyclohexylenediamine, and N,N'-dibenzyl-xylylenediamine.

[0091] In particularly preferred embodiments, the dental compositions of the present invention comprise one or more primary aliphatic diamines. Preferably, the dental compositions comprise one primary aliphatic diamine.

[0092] Preferably, the primary aliphatic diamine has the following formula (III):

[0093] [ka]

[0094] (In the formula, Q' is a substituted or unsubstituted C 3-20 Alkylene group or substituted or unsubstituted C 3-20 represents a cycloalkylene group, and 3-20 Alkylene groups and substituted C 3-20 The cycloalkylene group may contain one or more fluorine atoms, hydroxyl groups, C 1-6 Alkyl group, C 3-12 Cycloalkyl groups, C 1-6 Alkoxy group, C 1-6 Alkylthio group, C 6-10 Aryl group, C 6-10 Aryloxy group, C 7-14 Aryl alkyl group or C 7-14 (optionally substituted by an arylalkoxy group) is a compound of

[0095] In the compound of formula (III), preferably, Q′ is a substituted or unsubstituted C 3-20 More preferably, Q' represents a substituted cycloalkylene group, and even more preferably, Q' represents a substituted cycloalkylene group, wherein the substituents are one or more C 1-6 Alkyl group, C 3-12 represents a substituted cycloalkylene which may be a cycloalkyl group.

[0096] In a particularly preferred embodiment, the dental composition of the present invention comprises a primary aliphatic diamine selected from the group consisting of octahydro-4,7-methano-1H-indenedimethylamine (CAS: 68889-71-4) and isophoronediamine (CAS: 2855-13-2).

[0097] Further optional ingredients In addition to the above components, the dental composition of the present invention may contain further optional components. The dental composition of the present invention can optionally contain any additives suitable for dental use and / or known in the art.

[0098] For example, the dental composition of the present invention may contain water or any solvent known in the art, and preferably contains 5 to 20 wt % of water or any solvent known in the art, based on the total weight of the composition.

[0099] Optionally, the dental composition may further comprise a stabilizer and / or a pigment.

[0100] Preferably, the dental composition of the present invention is a root canal filling composition or a pulp capping composition, more preferably a root canal filling composition.

[0101] The dental composition of the present invention has a gelation time of at most 20 hours. Preferably, the dental composition of the present invention has a gelation time of at most 18 hours, and more preferably, the dental composition of the present invention has a gelation time of at most 15 hours.

[0102] Furthermore, the present invention provides a compound of formula (I) for use in the treatment or prevention of endodontic disease.

[0103] [ka]

[0104] During the ceremony, L is one or more fluorine atoms, hydroxyl groups, C 1-6 Alkoxy group, C 1-6 Alkylthio group, C 6-10 Aryl group, C 6-10 Aryloxy group, C 7-14 Aryl alkyl group or C 7-14 a linear or branched hydrocarbon group having 1 to 8 carbon atoms, optionally substituted by an arylalkoxy group; A 1 , A 2 and A 3 At least one of the groups represents CH, and the remaining groups represent CR groups. 1 and; X 1 , X 2 , X 3 , Y 1 , Y 2 and Y 3 At least three of the groups represent CH, and the remaining groups are CHR 2 group, CR 3 R 4 or C=NR 5 and; n is 0 or 1; R 1 is a fluorine atom, a hydroxyl group, an amino group, C 1-6 Alkyl group, C 1-6 Alkoxy group, C 1-6 Alkylthio group, C 6-10 Aryl group, C 6-10 Aryloxy group, C 7-14 Aryl alkyl group or C 7-14 is an arylalkoxy group; R 2 is a fluorine atom, a hydroxyl group, an amino group, C 1-6 Alkyl group, C 1-6 Alkoxy group, C 1-6 Alkylthio group, C 6-10 Aryl group, C 6-10 Aryloxy group, C 7-14 Aryl alkyl group or C 7-14 is an arylalkoxy group; R 3 and R 4may be the same or different and independently represent a fluorine atom, C 1-6 Alkyl group, C 1-6 Alkoxy group, C 1-6 Alkylthio group, C 6-10 Aryl group, C 6-10 Aryloxy group, C 7-14 Aryl alkyl group or C 7-14 represents an arylalkoxy group, or R 3 and R 4 and may be joined together with the carbon atoms to which they are attached to form a 3- to 6-membered saturated hydrocarbon ring; R 5 is a hydroxyl group, an amino group, C 1-6 Alkyl group, C 1-6 Alkoxy group, C 6-10 Aryl group, C 6-10 Aryloxy group, C 7-14 Aryl alkyl group or C 7-14 is an arylalkoxy group; However, when n is 0, R 1 , R 2 , R 3 / R 4 and R 5 At least one of the following is present.

[0105] The present invention will now be further illustrated by the following examples.

[0106] Example material Rimantadine (1-(1-adamantyl)ethylamine) hydrochloride was purchased from abcr and converted to the free base by stirring in a mixture of diethyl ether and sodium hydroxide solution (2N) followed by extraction with diethyl ether. Removal of the solvent under reduced pressure afforded the free rimantadine base in quantitative yield. Bisphenol A diglycidyl ether (Araldite GY 250, CAS 25068-38-6) and bisphenol F diglycidyl ether (Araldite GY 285, CAS 9003-36-5). TCD diamine (3(4),8(9)-di(aminomethyl)trichloro[5.2.1.0(2.6)]decane, CAS 68889-71-4) was purchased from Oxea GmbH. Isophoronediamine (IPDA) was purchased from Sigma-Aldrich. N,N'-Dibenzyl-5-oxanonanediamine-1,9 (OPC-91) was obtained from AMB LIFE & SIENCE ApS. CaWO4 (1 μm and 6 μm, Grade B) particles were purchased from Starck HC GmbH. Aerosil 200 was provided by CSC Jakle Chemie. SICOVIT® (Yellow 10 E 172) was purchased from Simon und Werner GmbH. All other chemicals were purchased from common chemical suppliers.

[0107] Gel time [Method] The amine paste and epoxide paste were mixed on a mixing plate using a spatula (m Amine / m Epoxide The mixing ratio is given for each application. Mixing was applied for 30 seconds until a homogeneous paste-paste mixture was achieved. The mass of each individual paste was measured by a balance with an accuracy of ±0.0001 g. Approximately 6 g of the paste-paste mixture was transferred to a glass vial (10 mL) equipped with a round-cut plastic lid and a glass rod. The glass rod must be in contact with the paste mixture. The vial was placed in a climate chamber at 37 °C (t0) (temperature controlled [ΔT = ±1 °C]) and a relative humidity of 30-50%. Gelation was achieved when the glass rod could no longer be rotated (tgelation ).

[0108] Paste Mixing See AH Plus® AH Plus Amine Paste (Batch No.: 1901000196) was compared with AH Plus Epoxide Paste (Batch No.: 1812100076). Amine / m Epoxide =0.86207. The mixed paste exhibited a gel time of less than 16 hours (method described above), a flow of 23±0 mm (ISO 6876:2012) and a film thickness of 20±8 μm (ISO 6876:2012).

[0109] Paste A1 Preparation of Epoxide Paste A1 (SAR3-08-01) Bisphenol A diglycidyl ether (7.7205 g), bisphenol F diglycidyl ether (0.9766 g), CaWO4 Grade B (16.9399 g), CaWO4 (1 μm) (4.2365 g), and SICOVIT® (Yellow 10 E172) (0.0438 g) were added, and high-speed mixing was applied (2150 rpm for 1 minute). Aerosil® 200 (0.0850 g) was added, and a high-speed mixer run was performed (2150 rpm for 1 minute). The paste was manually mixed with a spatula to disperse filler residue from the container wall, and another high-speed mixer run was performed (2150 rpm for 1 minute) to obtain a homogeneous, pale yellow paste. Density (T=23°C): 2.7277 g / mL (measured by helium pycnometer).

[0110] Preparation of Amine Paste A1 (SAR3-06-01) Rimantadine (1-(1-adamantyl)ethylamine) (1.4835 g), N,N'-dibenzyl-5-oxanonanediamine-1,9 (OPC-91) (3.3351 g), and isophoronediamine (IPDA) (0.1983 g) were transferred to a high-speed mixer vessel and mixed at 2150 rpm for 5 minutes. CaWO (1 μm) (4.8203 g) and CaWO Grade B (19.2703 g) were added, and high-speed mixing was applied (2150 rpm, 1000 mBar for 5 minutes). Aerosil® 200 (0.5847 g) and Baysilone M500 (0.3189 g) were added, and the paste was mixed manually with a spatula to disperse filler residue from the container walls, followed by another high-speed mixer run (1 min at 2150 rpm) to obtain a homogeneous white paste. Density (T=23°C): 3.0609 g / mL (measured by helium pycnometer).

[0111] Mixture of Paste A1 (SAR3-06-01 + SAR3-08-01) Amine paste A1 and epoxide paste A1 were compared. Amine / m Epoxide =0.89112. The mixed paste exhibited a gel time of less than 16 hours (SAR3-25-1), a flow of 23.3 ± 0.5 mm, and a film thickness of 27 ± 5 μm (all in accordance with ISO 6876:2012).

[0112] Paste A2 Preparation of Epoxide Paste A2 (SAR3-07-01) Bisphenol A diglycidyl ether (6.5473 g), bisphenol F diglycidyl ether (0.8571 g), CaWO4 Grade B (22.5025 g) and SICOVIT® (Yellow 10 E172) (0.0423 g) were added and high speed mixing was applied (1 minute at 2150 rpm). 200After adding 0.0844 g of cellulose, a high-speed mixer run was performed (1 minute at 2150 rpm). The paste was manually mixed with a spatula to disperse any filler residue from the container walls, followed by another high-speed mixer run (1 minute at 2150 rpm) to obtain a homogeneous, pale yellow paste. Density (T=23°C): 2.9568 g / mL (measured by helium pycnometer).

[0113] Preparation of Amine Paste A2 (SAR3-05-01) Rimantadine (1-(1-adamantyl)ethylamine) (1.3287 g), N,N'-dibenzyl-5-oxanonanediamine-1,9 (OPC-91) (2.9887 g), and isophoronediamine (IPDA) (0.1983 g) were transferred to a high-speed mixer vessel and mixed at 2150 rpm for 5 minutes. CaWO4 Grade B (24.5983 g) was added, and high-speed mixing was applied (2150 rpm, 1000 mBar for 5 minutes). Aerosil® 200 (0.5849 g) and Baysilone M500 (0.3165 g) were added, and the paste was mixed manually with a spatula to disperse any filler residue from the vessel wall. Another high-speed mixer run was then performed (2150 rpm for 1 minute) to obtain a homogeneous white paste. Density (T=23°C): 3.2928 g / mL (measured by helium pycnometer).

[0114] Mixture of Paste A2 (SAR3-05-01 + SAR3-07-01) Amine paste A2 and epoxide paste A2 were compared. Amine / m Epoxide =0.89797. The mixed paste exhibited a gel time of less than 16 hours (SAR3-24-02), a flow of 22.7 ± 0.5 mm, and a film thickness of 20 ± 2 μm (all in accordance with ISO 6876:2012).

[0115] Paste A3 Preparation of Epoxide Paste A3 (SAR3-171-01) Bisphenol A diglycidyl ether (7.7238 g), bisphenol F diglycidyl ether (0.9798 g), CaWO4 Grade B (16.9416 g), CaWO4 (1 μm) (4.2352 g) and SICOVIT® (Yellow 10 E172) (0.0425 g) were added and high speed mixing was applied (1 minute at 2150 rpm). 200 After adding 0.0843 g of cellulose acetate, a high-speed mixer run was performed (1 minute at 2150 rpm). The paste was manually mixed with a spatula to disperse filler residue from the container walls, followed by another high-speed mixer run (1 minute at 2150 rpm) to obtain a homogeneous, pale yellow paste. Density (T=23°C): 2.7255 g / mL (measured by helium pycnometer).

[0116] Preparation of Amine Paste A3 (SAR3-172-01) Rimantadine (1-(1-adamantyl)ethylamine) (1.4856 g), N,N'-dibenzyl-5-oxanonanediamine-1,9 (OPC-91) (3.3376 g), and 3(4),8(9)-di(aminomethyl)trichloro[5.2.1.0(2.6)]decane (TCD diamine) (0.1909 g) were transferred to a high-speed mixer and mixed at 2150 rpm for 5 minutes. CaWO4 Grade B (2.4096 g) and CaWO4 (1 μm) (21.6828 g) were added, and high-speed mixing was applied (2150 rpm, 1000 mBar) for 5 minutes. Aerosil® 200 (0.6325 g) and Baysilone M500 (0.2685 g) were added and the paste was mixed manually with a spatula to disperse filler residue from the container wall, followed by another high-speed mixer run (1 min at 2150 rpm) to obtain a homogeneous white paste. Density (T=23°C): 3.1421 g / mL (measured by helium pycnometer).

[0117] Paste A3 mixture (SAR3-171-01 + SAR3-172-01) Amine Paste A3 and Epoxide Paste A3 were compared. Amine / m Epoxide= 0.86742. The mixed pastes exhibited a gel time of less than 16 hours (SAR4-15-01), a flow of 21.0 ± 0.0 mm (SAR4-16-02), and a film thickness of 8 ± 2 μm (SAR4-16-01), all in accordance with ISO 6876:2012.

[0118] Paste A4 Preparation of Epoxide Paste A4 (SAR3-173-01) Bisphenol A diglycidyl ether (8.6969 g), CaWO4 Grade B (19.0581 g), CaWO4 (1 μm) (2.1156 g) and SICOVIT® (Yellow 10 E172) (0.0437 g) were added and high speed mixing was applied (1 minute at 2150 rpm). 200 After adding 0.0850 g of cellulose acetate, a high-speed mixer run was performed (1 minute at 2150 rpm). The paste was manually mixed with a spatula to disperse any filler residue from the container walls, followed by another high-speed mixer run (1 minute at 2150 rpm) to obtain a homogeneous, pale yellow paste. Density (T=23°C): 2.6902 g / mL (measured by helium pycnometer).

[0119] Preparation of Amine Paste A4 (SAR3-174-01) Rimantadine (1-(1-adamantyl)ethylamine) (1.4824 g), N,N'-dibenzyl-5-oxanonanediamine-1,9 (OPC-91) (3.3362 g), and 3(4),8(9)-di(aminomethyl)trichloro[5.2.1.0(2.6)]decane (TCD diamine) (0.1912 g) were transferred to a high-speed mixer and mixed at 2150 rpm for 5 minutes. CaWO4 Grade B (4.8162 g) and CaWO4 (1 μm) (19.2744 g) were added, and high-speed mixing was applied (2150 rpm, 1000 mBar) for 5 minutes. Aerosil® 200 (0.5413 g) and Baysilone M500 (0.3596 g) were added and the paste was mixed manually with a spatula to disperse filler residue from the container wall, followed by another high-speed mixer run (1 min at 2150 rpm) to obtain a homogeneous white paste. Density (T=23°C): 3.1541 g / mL (measured by helium pycnometer).

[0120] Paste A4 mixture (SAR3-173-01 + SAR3-174-01) Amine Paste A4 and Epoxide Paste A4 were compared. Amine / m Epoxide = 0.85292. The mixed pastes exhibited a gel time of less than 16 hours (SAR4-15-02), a flow of 21.3 ± 0.5 mm (SAR4-17-02), and a film thickness of 8 ± 2 μm (SAR4-17-01), all in accordance with ISO 6876:2012.

[0121] Paste A5 (comparison) Preparation of Epoxide Paste A5 (SAR3-173-01) Bisphenol A diglycidyl ether (8.6969 g), CaWO4 Grade B (19.0581 g), CaWO4 (1 μm) (2.1156 g) and SICOVIT® (Yellow 10 E172) (0.0437 g) were added and high speed mixing was applied (1 minute at 2150 rpm). 200After adding 0.0850 g of cellulose acetate, a high-speed mixer run was performed (1 minute at 2150 rpm). The paste was manually mixed with a spatula to disperse any filler residue from the container walls, followed by another high-speed mixer run (1 minute at 2150 rpm) to obtain a homogeneous, pale yellow paste. Density (T=23°C): 2.6902 g / mL (measured by helium pycnometer).

[0122] Preparation of Amine Paste A5 (SAR3-175-01) 3-Aminoadamantan-1-ol (1.4824 g), N,N'-dibenzyl-5-oxanonanediamine-1,9 (OPC-91) (3.3362 g), and 3(4),8(9)-di(aminomethyl)trichloro[5.2.1.0(2.6)]decane (TCD diamine) (0.1912 g) were transferred to a high-speed mixer and mixed at 2150 rpm for 5 min. CaWO4 Grade B (4.8162 g) and CaWO4 (1 μm) (19.2744 g) were added, and high-speed mixing was applied (2150 rpm, 1000 mBar, 5 min). Aerosil® 200 (0.5413 g) and Baysilone M500 (0.3596 g) were added and the paste was mixed manually with a spatula to disperse filler residue from the container wall, followed by another high-speed mixer run (1 min at 2150 rpm) to obtain a homogeneous white paste. Density (T=23°C): 3.1541 g / mL (measured by helium pycnometer).

[0123] Paste A5 mixture (SAR3-173-01 + SAR3-175-01) Amine Paste A5 and Epoxide Paste A5 were compared. Amine / m Epoxide =0.85292. The mixed paste exhibited a gel time of 18 hours, a flow of 13.0±0.5 mm, and a film thickness of 97±2 μm (none of which met the requirements of ISO 6876:2012).

Claims

1. (i) one or more di- or polyepoxides; (ii) a compound represented by the following formula (I): 【Chemistry 14】 (In the formula, L is the following group: 【Chemistry 15】 represents; A 1 , A 2 and A 3 represents CH, and X 1 , X 2 , X 3 , Y 1 , Y 2 and Y 3 is CH 2 represents; n is 1) Compounds of A dental composition comprising:

2. The one or more di- or polyepoxides have the following formula (II): 【Chemistry 16】 (In the formula, Q is an (m+1)-valent organic group; R 6 , R 7 and R 10 may be the same or different and independently represent a hydrogen atom or C 1-6 represents an alkyl group, R 8 , R 9 and R 11 may be the same or different and independently represent a hydrogen atom or C 1-6 represents an alkyl group, m is an integer from 1 to 3.

2. The dental composition of claim 1, wherein the compound is

3. The following structure: 【Chemistry 17】 (In the formula, R 10 is hydrogen or a C 1-6 alkyl group; R 12 is hydrogen or substituted or unsubstituted C 1-18 alkyl group, substituted or unsubstituted C 3-18 a cycloalkyl group or a substituted or unsubstituted C 7-18 is an arylalkyl group, R 13 is a bifunctional substituted or unsubstituted C 1 ~C 18 an alkylene group or a substituted or unsubstituted cycloalkylene group; A' is a moiety derived from the addition reaction of a di- or polyepoxide of formula (II) with an amine; c is an integer) 3. The dental composition of claim 2, further comprising an aliphatic polyamine selected from the compounds of formula (I).

4. The dental composition of any one of claims 1 to 3, further comprising a radiopaque particulate filler.

5. The dental composition according to any one of claims 1 to 4, which is a root canal filling composition or a pulp-capping composition.

6. The dental composition according to any one of claims 1 to 5, which has a gel time of at most 20 hours.

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