A curable dental composition comprising an addition-fragmentation agent and a curable dental resin is disclosed.
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1. A curable dental composition comprising: a) at least one dental resin comprising at least two ethylenically unsaturated groups;b) an addition-fragmentation agent comprising:1) a labile addition-fragmentation group; and2) at least two surface-binding functional groups; andc) optionally an inorgani
1. A curable dental composition comprising: a) at least one dental resin comprising at least two ethylenically unsaturated groups;b) an addition-fragmentation agent comprising:1) a labile addition-fragmentation group; and2) at least two surface-binding functional groups; andc) optionally an inorganic oxide filler,wherein the addition-fragmentation agent is of the formula: whereinR1, R2 and R3 are each independently Y-Q′-, a (hetero)alkyl group or a (hetero)aryl group with the proviso that at least two of R′, R2 and R3 is Yp-Q′-Q′ is a covalent bond or a linking group having a valence of p+1;Y is a surface-binding organic functional group;p is 1 or 2;X1 is independently —O— or —NR4—, where R4 is H or C1-C4 alkyl, andn is 0 or 1whereinY-Q′ is selected from a monophosphate, a phosphonate group, a phosphonic acid group, a hydroxamic acid group, a carboxylic acid group, and acetoacetate group, an anhydride group, an isonitrile group, a silyl group, a disulfide group, a thiol group, an amino group, a sulfinic acid group, a sulfonic acid group, a phosphine group, a phenolic group or a heterocyclic aromatic group. 2. The dental composition of claim 1 wherein Q′ is selected from —O—, —S—, —N(R4)—, —SO2—, —PO2—, —CO—, —OCO—, —R6—, —N(R4)—CO—N(R4)—, —N(R4)—CO—O—, —N(R4)—CO—N(R4)—CO—O—R6—, —CO—N(R4)—R6—, —R6—CO—O—R6—, —O—R6—, —S—R6—, —N(R4)—R6—, —SO2—R6—, —PO2—R6—, —CO—R6—, —OCO—R6—, —N(R4)—CO—R6—, —N(R4)—R6—CO—O—, and —N(R4)—CO—N(R4)—, wherein each R4 is hydrogen, a C1 to C4 alkyl group, or aryl group, each R6 is an alkylene group having 1 to 6 carbon atoms, a 5- or 6-membered cycloalkylene group having 5 to 10 carbon atoms, or a divalent arylene group having 6 to 16 carbon atoms, with the proviso that Q-Z does not contain peroxidic linkages. 3. The dental composition of claim 1 wherein Q′ is an alkylene of the formula —CrH2r—, where r is 1 to 10. 4. The dental composition of claim 1 wherein Q′ is a hydroxyl-substituted alkylene of the formula —CH2—CH(OH)—CH2—. 5. The dental composition of claim 1 wherein Q′ is an aryloxy-substituted alkylene, or an alkoxy-substituted alkylene. 6. The dental composition of claim 1 wherein the ethylenically unsaturated groups of the dental resin are (meth)acrylate groups. 7. The dental composition of claim 1 wherein the dental resin comprises an aromatic monomer having a refractive index of at least 1.50. 8. The dental composition of claim 1 wherein the dental resin is a low volume shrinkage resin. 9. The dental composition of claim 1 wherein the dental resin is an isocyanurate resin, a tricyclodecane resin, cyclic allylic sulfide resins; methylene dithiepane silane resins; and poly(meth)acryloyl-containing resins, or mixtures thereof. 10. The dental composition of claim 1 wherein the dental composition further comprises at least one other (meth)acrylate monomer is selected from the group consisting of ethoxylated bisphenol A dimethacrylate, 2-hydroxyethyl methacrylate, bisphenol A diglycidyl dimethacrylate, urethane dimethacrylate, triethlyene glycol dimethacrylate, glycerol dimethacrylate, ethylenegylcol dimethacrylate, neopentylglycol dimethacrylate (NPGDMA), polyethyleneglycol dimethacrylate, and mixtures thereof. 11. The dental composition of claim 1 wherein the inorganic oxide filler comprises nanoparticles. 12. The dental composition of claim 1 comprising a surface modified inorganic oxide filler. 13. A method of treating a tooth surface, the method comprising a) providing a curable dental resin of claim 1;b) placing the dental composition on a tooth surface in the mouth of a subject; andc) hardening the hardenable dental composition. 14. The curable dental composition of claim 1 comprising a universal dental restorative comprising: a) 15-30 wt % of a curable dental resin comprising at least two polymerizable, ethylenically unsaturated groups;b) 70-85 wt % of an inorganic filler;c) 0.1 to 10 parts by weight of the addition-fragmentation agent, relative to 100 parts by weight of a) and b),said curable composition further comprising an initiator and; <2% of stabilizers and pigments. 15. The curable dental composition of claim 1 comprising a flowable restorative composite comprising: a) 25-50 wt % of a curable dental resin comprising at least two polymerizable, ethylenically unsaturated groups;b) 50-75 wt % of an inorganic filler;c) 0.1 to 10 parts by weight of the addition-fragmentation agent relative to 100 parts by weight of a) and b);d) an initiator;e) <2% stabilizers and pigments,f) optionally 5-60 wt. % monomers having an acid-functional group; andg) an initiator. 16. The curable dental composition of claim 1 comprising a resin-modified glass-ionomer adhesive comprising: a) 10-25 wt. % of a partially (meth)acrylated poly(meth) acrylic acid;b) 5-20% of a hydroxyalkyl (meth)acrylate;c) 30-60% of fluoroaluminosilicate (FAS) acid reactive glass;d) 0-20% non-acid reactive fillers;e) 10-20% water;f) 0.1 to 10 wt. % of the addition-fragmentation agent, relative to 100 parts by weight of a) and b); andg) an initiator. 17. The curable dental composition of claim 1 further comprising a surface-modified inorganic filler of the formula: where Filler is an inorganic filler particle,R2 is Yp-Q′-, a (hetero)alkyl group or a (hetero)aryl group;Q′ is a covalent bond or an organic (hetero)hydrocarbyl linking group having a valence of p+1;Y′ is the residue of the surface-binding functional group Y;p is 1 or 2;X1 is independently —O— or —NR4—, where R4 is H or C1-C4 alkyl, andn is 0 or 1. 18. The curable dental composition of claim 17 wherein the Filler is silica. 19. The curable dental composition of claim 17 wherein the group Filler-Y′p— is of the formula Silica-O—Si(R7)2— wherein each R7 group is independently selected from the group of alkoxy, acetoxy, and halide.
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