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 of the formula: whereinR1, R2 and R3 are each independently Zm-Q-, Yp-Q′-, a (hetero)alkyl group or a (hetero)aryl group with the provi
1. A curable dental composition comprising: a) at least one dental resin comprising at least two ethylenically unsaturated groups;b) an addition-fragmentation agent of the formula: whereinR1, R2 and R3 are each independently Zm-Q-, Yp-Q′-, a (hetero)alkyl group or a (hetero)aryl group with the proviso that at least one of the R1, R2 and R3 is Zm-Q-, and with the proviso that at least one of the R1, R2 and R3 is Yp-Q′-Q is a covalent bond or a linking group, having a valence of m+1;Q′ is a covalent bond or a linking group, having a valence of p+1;Z is an ethylenically unsaturated polymerizable group,Y is a functional group that bonds to, or etches a dental structure on which the addition-fragmentation agent is disposed;m is 1 to 6;p is 1 or 2;each X1 is independently —O— or —NR4—, where R4 is H or C1-C4 alkyl, andn is 0 or 1; andc) optionally an inorganic oxide filler. 2. The dental composition of claim 1 wherein at least on of R1, R2 and R3 of the addition-fragmentation agent contain both Zm-Q- and Yp-Q′-, where Q is a covalent bond or a linking group, having a valence of m+1;Q′ is a covalent bond or a linking group, having a valence of p+1;Z is an ethylenically unsaturated polymerizable group,m is 1 to 6;p is 1 or 2; andY is a functional group that bonds to, or etches a dental structure on which the addition-fragmentation agent is disposed. 3. The dental composition of claim 2 wherein Z of the addition-fragmentation agent comprises a vinyl, vinyloxy, (meth)acryloxy, (meth)acrylamido, styrenic and acetylenic functional groups. 4. The dental composition of claim1 wherein Q is selected from —O—, —S—, —NR4—, —SO2—, —PO2—, —CO—, —OCO—, —R6—, —NR4—CO—NR4—, —NR4—CO—O—, —NR4—CO—NR4—CO—O—R6—, —CO—NR4—R6—,—R6—CO—O—R6—, —O—R6—S—R6—, —NR4—R6—,—SO2—R6—, —PO2—R6—,—CO—R6—, —OCO—R6—, —NR4—CO—R6—, —NR4—R6—CO—O—, and —NR4—CO—NR4—, 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. 5. The dental composition of claim 1 wherein Q and/or Q′ is an alkylene. 6. The dental composition of claim 1 wherein Q and/or Q′ is a hydroxyl-substituted alkylene. 7. The dental composition of claim 1 wherein the ethylenically unsaturated groups of the dental resin are (meth)acrylate groups. 8. 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. 9. The dental composition of claim 1 wherein the hardened dental composition exhibits a stress deflection no greater than 0.6. 10. The dental composition of claim 1 wherein the dental composition further comprises at least one other (meth)acrylate monomer is selected from 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. The curable dental composition of claim 12 comprising a surface-modified inorganic oxide filler of the formula: whereFiller is an inorganic oxide filler particle,R2 and R3 are each independently Zm-Q-, Yp-Q′-, a (hetero)alkyl group or a (hetero)aryl group;Q is a covalent bond or a linking group, having a valence of m +1;Q′ is a covalent bond or an or a linking group, having a valence of p +1;Z is an ethylenically unsaturated polymerizable group,Y′ is the residue of the functional group Y;m is 1 to 6;p is 1 or 2;X1 is independently —O- or —NR4—, where R4 is H or C1-C4 alkyl, andn is 0 or 1. 14. A method of treating a tooth surface, the method comprising a) providing a curable dental composition of claim 1;b) placing the dental composition on a tooth surface in the mouth of a subject; andc) curing the curable dental composition. 15. 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 of claim 1, relative to 100 parts by weight of a) and b),said curable composition further comprising an initiator and;<2%, stabilizers, or pigments. 16. 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, andf) optionally 5-60 wt. %% monomers having a acid- functional group. 17. 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; andf) 0.1 to 10 wt. % of the addition-fragmentation agent, relative to 100 parts by weight of a) and b). 18. The curable dental composition of claim 1 comprising a dental adhesive comprising: a) 30-8-wt. % mono (meth)acrylate) monomers;b) 1-10 wt. % polyfunctional (meth)acrylate monomers;c) 5-60 wt. % monomers having a acid- functional group;d) 0-10, poly(meth)acrylic acid methacrylate monomers;e) 0.1 to 10 wt. % of the addition-fragmentation agent, relative to 100 parts by weight of a) to d);f) an initiator,g) 0-30% inorganic filler, relative to 100 parts by weight of a) to d);h) 0 to 25 wt. % solvent relative to 100 parts by weight of a) to d);i) 0 to 25 wt. % water relative to 100 parts by weight of a) to d); and <2% stabilizers and pigments.
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