MODIFIED DIMETHYLACRYLATE MONOMER, METHOD FOR PREPARING THE SAME, AND POLYMERIC DENTAL COMPOSITE
A modified dimethylacrylate monomer is represented by the following formula (I): wherein R 11 and R 12 independently represent a C 1 to C 3 alkylene group or a phenylene group; X 1 and X 2 independently represent NHCO, CO, or a single bond; Y 1 and Y 2 independently represent a C 1 -C 10 alkylene group or a single bond; and Z 1 and Z 2 independently represent SiA 1 A 2 A 3 or H, with the proviso that, Z 1 and Z 2 cannot be H at the same time. A method for preparing the modified dimethylacrylate monomer and a polymeric dental composite are also disclosed.
1 . A modified dimethylacrylate monomer represented by the following formula (I):
wherein R 11 and R 12 independently represent a C 1 to C 3 alkylene group or a phenylene group; X 1 and X 2 independently represent NHCO, CO, or a single bond; Y 1 and Y 2 independently represent a C 1 -C 10 alkylene group or a single bond; and
Z 1 and Z 2 independently represent SiA 1 A 2 A 3 or H, with the proviso that, Z 1 and Z 2 cannot be H at the same time,
wherein A 1 , A 2 , and A 3 independently represent R 21 B or R 21 DR 22 , R 2 , represents a C 1 to CIO alkylene group or a single bond, B represents NCO, COOH, OH, or H, D represents NHCO, CO, COO, or CHCH, and R 22 represents H or a C 1 to C 5 alkyl group which is un-substituted or substituted with a hydroxyl group, with the proviso that, when R 22 is H, D cannot be NHCO or CO.
2 . The modified dimethylacrylate monomer of claim 1 , wherein R 11 and R 12 are a methylene group.
3 . The modified dimethylacrylate monomer of claim 1 , wherein A 1 , A 2 , and A 3 independently represent R 21 B or R 21 DR 22 , R 21 represents a C 1 to C 10 alkylene group or a single bond, B represents NCO, COOH, or H, D represents NHCO, CO, COO, or CHCH, and R 22 represents H or an un-substituted C 1 to C 5 alkyl group, with the proviso that, when R 22 is H, D cannot be NHCO or CO.
4 . The modified dimethylacrylate monomer of claim 1 , wherein X 1 , X 2 , Y 1 , and Y 2 are independently a single bond; Z 2 is H; and Z 1 is SiA 1 A 2 A 3 , and wherein A 1 , A 2 , and A 3 are independently R 21 B.
5 . The modified dimethylacrylate monomer of claim 4 , wherein R 21 is ethylene and B is H.
6 . The modified dimethylacrylate monomer of claim 1 , wherein X 1 , X 2 , Y 1 , and Y 2 are independently a single bond; Z 1 and Z 2 are independently SiA 1 A 2 A 3 ; and A 1 , A 2 , and A 3 are independently R 21 B.
7 . The modified dimethylacrylate monomer of claim 6 , wherein R 21 is ethylene and B is H.
8 . A method for preparing a modified dimethylacrylate monomer of claim 1 , comprising reacting a dimethylacrylate monomer represented by the following formula (II):
wherein R 11 and R 12 independently represent C 1 to C 3 alkylene or phenylene,
with a silane compound represented by the following formula (III):
SiA 1 A 2 A 3 A 4 (III)
wherein A 1 , A 2 , and A 3 independently represent R 21 B or R 21 DR 22 , and A 4 represents R 21 E, wherein R 21 is C 1 -C 10 alkylene or a single bond, B represents Cl, Br, NCO, COCl, COOH, OH, or H, D represents NHCO, CO, COO, or CHCH, E represents Cl, Br, NCO, COCl, COOH, OH, or H, and R 22 represents H or a C 1 to C 5 alkyl group which is un-substituted or substituted with a hydroxyl group, with the proviso that, when R 22 is H, D cannot be NHCO or CO.
9 . The method of claim 8 , wherein the reaction is conducted in the presence of an organic base having a pH ranging from 8 to 14.
10 . The method of claim 9 , wherein the reaction is conducted in the presence of a catalyst.
11 . A polymeric dental composite prepared by reacting a mixture, said mixture containing:
modified dimethylacrylate monomers as claimed in claim 1 ;
an inorganic filler; and
a photo-initiation system.
12 . The polymeric dental composite of claim 11 , wherein, based on the total weight of said mixture, said modified dimethylacrylate monomers are present in an amount ranging from 5 to 60 wt %.
13 . The polymeric dental composite of claim 11 , wherein, based on the total weight of said mixture, said inorganic filler is present in an amount ranging from 40 to 95 wt %.
14 . The polymeric dental composite of claim 13 , wherein said inorganic filler is selected from the group consisting of; quartz, silicon, silicon oxide, aluminum oxide, aluminum silicate, aluminum barium silicate, barium sulfate, barium glass, zirconium oxide, lithium aluminum silicate, and combinations thereof.
15 . The polymeric dental composite of claim 11 , wherein said photo-initiation system includes a photo-initiator and a reductant, and wherein, based on the total weight of said mixture, said photo-initiator is present in an amount ranging from 0.01 to 5 wt %, said reductant being present in an amount ranging from 0.01 to 5 wt %.
16 . The polymeric dental composite of claim 11 , wherein said mixture further includes dimethylacrylate monomers having the following formula (II):
wherein R 11 and R 12 independently represent a C 1 to C 3 alkylene group or a phenylene group.
17 . The polymeric dental composite of claim 16 , wherein, based on the total weight of said mixture, said dimethylacrylate monomers having the formula (II) are present in an amount ranging from 5 to 60 wt %.
18 . The polymeric dental composite of claim 11 , wherein said mixture further includes a polymerization inhibitor having an amount ranging from 0.01 to 5 wt % based on the total weight of said mixture.
19 . The polymeric dental composite of claim 18 , wherein said polymerization inhibitor is hydroquinone, hydroquinone monoethyl ether, or hydroquinone monomethyl ether.