Polymerizable resins containing a 1,3,5-hexahydro-1,3,5-triazine moiety, methods of making, and dental compositions containing the same
Disclosed herein are methods of making polymerizable resins containing a 1,3,5-hexahydro-1,3,5-triazine moiety and dental compositions comprising such novel hydrolytic stable, polymerizable resins derived from 1,3,5-triacryloyl-hexahydro-1,3,5-triazine (TAT).
1. A method of forming a hydrolytically-stable and water-soluble polymerizable resin containing a 1,3,5-hexahydro-1,3,5-triazine (TAT) moiety comprising:
reacting TAT in the presence of a Michael donor to yield mono-substituted TAT resin and di-substituted TAT resin present in a combined amount that is greater than a combined amount of tri-substituted resin TAT and remaining unreacted TAT; and
adding a (meth)acrylate resin to the mono-substituted TAT resin and di-substituted TAT resin.
2. The method of claim 1 , wherein the mono-and di-substituted TAT resins, respectively, have the following general formula:
wherein
X is H or CH 3 ,
R is CH 2 CH 2 -Y,
Y is —OR′, —SR′, —NHR″, —NR′R″, —NR′″, or R′—OCO—CH—CO—R′
R′ and R″ independently or the same are linear or branched linear alkyl having 1 to 18 carbon atoms with or without functional groups, and
R′″ is a cyclic alkyl having 2 to 18 carbon atoms or a heterocyclic compound.
3. The method of claim 2 , wherein functionalized R′ and R″ are of the general form R′(R″)-Z m , wherein m =1-3 and Z =—OH, —SH, —COOH, COOR′(R″)(R′″), —OPO(OH) 2 , —OPO(OR′)(OH), —PO(OH) 2 , —PO(OR′)(OH), —OSO 2 (OH), aromatics, or substituted aromatics.
4. The method claim 2 , wherein —NR′″ is imidazole or an imidazole derivative.
5. The method of claim 1 , wherein the hydrolysis stable polymerizable resin is reacted in the presence of a compound that yields a resin comprised of a TAT moiety with at least one acrylamide group.
6. The method of claim 1 , wherein the hydrolysis stable polymerizable resin is reacted in the presence of a compound that yields a resin comprised of a TAT moiety with at least one inorganic acidic group.
7. The method of claim 1 , wherein the hydrolysis stable polymerizable resin is reacted in the presence of a compound that yields a resin comprised of a TAT moiety with at least one imidazolium group.
8. The method of claim 1 , wherein the hydrolysis stable polymerizable resin is reacted in the presence of a compound that yields a resin comprised of a TAT moiety with at least one imidazole group.
9. The method of claim 1 further comprising adding a filler material after the step of reacting TAT with the Michael donor.