Dental composition
AssigneeDENTSPLY SIRONA Inc.
InventorsJoachim E Klee, Helmut Ritter, Sven Pohle, Oliver Elsner, Mareike Bardts
Life of this patent
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Abstract
A dental cement hardened by a cement reaction involving the specific polymerizable polyacidic polymer and optionally additional crosslinkable groups, has reduced shrinkage and improved mechanical properties, in particular with regard to flexural strength and fracture toughness. Moreover, the specific polymerizable polyacidic polymer of the present invention contains a high number of acidic groups which is not reduced by the presence of polymerizable moieties, whereby water solubility of the uncured polymer is not impaired by the presence of the polymerizable moieties.
Claims11
Dental cement composition comprising a polymerizable polyacidic polymer having repeating units in the polymer backbone, which are represented by the following formula (I), (II), and/or (III):
- wherein
- X represents O, S, or NR′, whereby R′ represents a hydrogen atom or a straight or branched C1-C6 alkyl group, C3-C6 cycloalkyl group, or C4-C8 cycloalkylalkyl group,
- Y represents a group of the following formula (IV)
- wherein each of L1, L2, L3 and L4,
- which are independent from each other represents a single bond, a straight or
- branched C1-C6 alkylene group, a straight or branched C alkenylene, or a straight or branched C1-C20 alkylene group which includes 1 to 8 atoms selected from oxygen and sulfur atoms,
- X′ represents O, S, or NR″, whereby R″ represents a hydrogen atom or a straight or branched C1-C6 alkyl group, C3-C6 cycloalkyl group, or C4-C8 cycloalkylalkyl group,
- m is 0 to 3, and
- n is 1 to 3, and
- wherein the dental cement composition further is a particulate glass comprising
- (a) 20-25% by weight of silica
- (b) 20-25% by weight of alumina
- (c) 18-21% by weight of CaO plus SrO
- (d) 13-18% by weight of zinc oxide
- (e) 14-18% by weight of P2O5
- (f) 4-7% by weight of fluoride,
- and wherein the content of Na2O is less than 1% by weight.
Process for preparing a polymerizable polyacidic polymer having repeating units in the polymer backbone which are represented by the following formula (I) and/or (II):
- wherein
- X represents O, S, or NR′, whereby R′ represents a hydrogen atom or a straight or branched C1-C6 alkyl group, C3-C6 cycloalkyl group, or C4-C8 cycloalkylalkyl group,
- Y represents a group of the following formula (IV)
- wherein each L1, L2, L3 and L4,
- which are independent from each other represents a single bond, a straight or
- branched C1-C6 alkylene group, a straight or branched C1-C6 alkenylene, or a straight or branched C1-C20 alkylene group which includes 1 to 8 atoms selected from oxygen and sulfur atoms,
- X′ represents O, S, or NR″, whereby R″ represents a hydrogen atom or a straight or branched C1-C6 alkyl group, C3-C6 cycloalkyl group, or C4-C8 cycloalkylalkyl group,
- m is 0 to 3, and
- n is 1 to 3,
- said process comprising the steps of
- (i) copolymerizing a mixture containing acrylic acid and one or more monomers selected from the group of maleic anhydride, itaconic anhydride, and
- (ii) reacting the reaction product of (i) with HXY, wherein
- X represents O, S, or NR′, whereby R′ represents a hydrogen atom or a straight or branched C1-C6 alkyl group, C3-C6 cycloalkyl group, or C4-C8 cycloalkylalkyl group,
- Y represents a group of the following formula (IV)
- wherein each of L1, L2, L3 and L4,
- which are independent from each other represents a single bond, a straight or branched C1-C6 alkylene group, a straight or branched C1-C6 alkenylene, or a straight or branched C1-C20 alkylene group which includes 1 to 8 atoms selected from oxygen and sulfur atoms,
- X′ represents O, S, or NR″, whereby R″ represents a hydrogen atom or a straight or branched C1-C6 alkyl group, C3-C6 cycloalkyl group, or C4-C8 cycloalkylalkyl group,
- m is 0 to 3, and
- n is 1 to 3.
Process for preparing a polymerizable polyacidic polymer having repeating units in the polymer backbone which are represented by the following formula (III)
- wherein
- X represents O, S, or NR′, whereby R′ represents a hydrogen atom or a straight or branched C1-C6 alkyl group, C3-C6 cycloalkyl group, or C4-C8 cycloalkylalkyl group,
- Y represents a group of the following formula (IV)
- wherein each L3 and L4
- which are independent from each other represents a single bond, a straight or branched C1-C6 alkylene group, a straight or branched C1-C6 alkenylene, or a straight or branched C1-C20 alkylene group which includes 1 to 8 atoms selected from oxygen and sulfur atoms,
- X′ represents O, S, or NR″, whereby R″ represents a hydrogen atom or a straight or branched C1-C6 alkyl group, C3-C6 cycloalkyl group, or C4-C8 cycloalkylalkyl group,
- m is 0 to 3, and
- n is 1 to 3,
- said process comprising the steps of reacting a carboxylic acid anhydride of YCOOH, wherein Y represents a group of the following formula (IV)
- wherein each of L1, L2, L3 and L4,
- which are independent from each other represents a single bond, a straight or
- branched C1-C6 alkylene group, a straight or branched C1-C6 alkenylene, or a straight or branched C1-C20 alkylene group which includes 1 to 8 atoms selected from oxygen and sulfur atoms,
- X′ represents O, S, or NR″, whereby R″ represents a hydrogen atom or a straight or branched C1-C6 alkyl group, C3-C6 cycloalkyl group, or C4-C8 cycloalkylalkyl group,
- m is 0 to 3, and
- n is 1 to 3
- with a polymer or copolymer containing repeating units of the following formula (V):
- wherein X represents O, S, or NR′, whereby R′ represents a hydrogen atom or a straight or branched C1-C6 alkyl group, C3-C6 cycloalkyl group, or C4-C8 cycloalkylalkyl group.
Dependencies are inferred from the claim text.