Polymerizable resins containing a 1,3,5-hexahydro-1,3,5-triazine moiety, methods of making, and dental compositions containing the same

Patent metadata

Field	Value
Publication number	US-9526676-B2
Application number	US-201414527828-A
Country	US
Kind code	B2
Filing date	Oct 30, 2014
Priority date	Oct 30, 2013
Publication date	Dec 27, 2016
Grant date	Dec 27, 2016

Abstract

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).

First claim

We claim:

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.

Assignees

• Dentsply Int Inc
• Dentsply Sirona Inc

Inventors

• Jin Xiaoming

Classifications

• A61K6/887

  Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• C07D211/06

  having no double bonds between ring members or between ring members and non-ring members · CPC title

• C07D251/04 Primary

  having no double bonds between ring members or between ring members and non-ring members · CPC title

• C07F9/6521

  Six-membered rings · CPC title

• C07F9/65583

  each of the hetero rings containing nitrogen as ring hetero atom · CPC title