Materials leading to improved dental composites and dental composites made therefrom

1. An uncured dental composite material comprising:

(i) a composition comprising at least one compound of the Formula I:

E 1 —R 1 n —O—R 2 —Q—R 3 —O—R 4 m —E 2   I

wherein:

Q is selected from the group consisting of:

(a) a carbocyclic ring containing 5 or 6 carbon atoms with up to 3 C 1-3 alkyl substituents on the ring;

(b) S—R 5 —T wherein S and T are each independently carbocyclic rings containing 5 or 6 carbon atoms with up to 3 C 1-3 alkyl substituents on the ring, and R 5 is a covalent bond or an alkylene group containing 1, 2, 3 or 4 carbon atoms; and

(c) a carbocyclic fused ring system containing two fused rings containing a total of 8 to 10 carbon atoms with up to 4 C 1-3 alkyl substituents on the fused ring system;

R 2 and R 3 are each independently selected from the group consisting of a covalent bond and an alkylene group containing 1, 2, 3, or 4 carbon atoms;

R 1 is a repeat unit of the formula

R 4 is a repeat unit of the formula

E 1 and E 2 are each independently

wherein R 6 is H (acryloyl) or CH 3 (methacryloyl); and

n and m are each independently an integer greater than 0;

a is independently an integer from 3 to 6;

a′ is independently an integer from 3 to 6; and

provided that neither R 2 nor R 3 is a covalent bond bonded directly to an aromatic ring; and

provided that the degree of polymerization of the at least one compound is between 2 and 30;

(ii) at least one compound of the Formula II

wherein:

each R 7 is independently hydrogen or methyl;

each R 8 is an alkylene having 2 to 14 carbon atoms, or an alkenylene having 2 to 8 carbon atoms, or a divalent alicyclic hydrocarbon having 5 to 14 carbon atoms, or a phenylene, which is optionally substituted with halogen or an alkyl group having 1 to 5 carbon atoms;

each R 9 is independently selected from the group consisting of hydrogen, acetyl, methyl, ethyl, C 3-6 linear alkyl, C 3-6 branched alkyl, and benzyl;

R 10 is independently selected from the group consisting of hydrogen, methyl, ethyl, C 3-6 linear alkyl, C 3-6 branched alkyl, phenyl, and benzyl; and

each A is a repeating unit of the formula:

wherein:

each R 11 is independently an alkylene having 2 or 3 carbon atoms,

each R 12 is independently an alkylene having 2 to 7 carbon atoms,

each R 13 is independently an alkylene having 2 to 5 carbon atoms,

p is an integer of 1 to 10,

and q is an integer of 1 to 10;

(iii) at least one polymerization initiator compound; and

(iv) at least one filler.

2. The uncured dental composite material of claim 1 , wherein the weight ratio of the at least one compound of the Formula Ito the at least one compound of Formula II is in the range from about 1:99 to about 25:75.

3. The uncured dental composite material of claim 1 , wherein Q is 1,4-cyclohexylene; R 2 and R 3 are each methylene, a=a′=5, E 1 =E 2 , R 6 is methyl, and the degree of polymerization is between 2 and 6.

4. The uncured dental composite material of claim 1 , wherein the compound of Formula II is:

5. The uncured dental composite material of claim 1 further comprising at least one photoinitiating accelerator, an activator, a pigment, a radiopaquing agent, a stabilizer, and an antioxidant.

6. A dental restoration article that is made by forming and curing the uncured dental composite material of claim 1 .