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-9944611-B2
Application number	US-201615352772-A
Country	US
Kind code	B2
Filing date	Nov 16, 2016
Priority date	Oct 30, 2013
Publication date	Apr 17, 2018
Grant date	Apr 17, 2018

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 hydrolytically-stable, polymerizable resins derived from a 1,3,5-hexahydro-1,3,5-triazine.

First claim

I claim:

1. A method of forming a hydrolytically-stable, water-soluble polymerizable resin containing a 1,3,5-hexahydro-1,3,5-triazine moiety, the method comprising:
reacting the 1,3,5-hexahydro-1,3,5-triazine moiety in the presence of a Michael donor under conditions selected to yield mono-substituted and di-substituted 1,3,5-hexahydro-1,3,5-triazine resin present in a combined amount that is greater than a combined amount of tri-substituted 1,3,5-hexahydro-1,3,5-triazine and unreacted 1,3,5-hexahydro-1,3,5-triazine moiety;
wherein the Michael donor is selected from the group consisting of a secondary amine and a thiol and the Michael donor is hydroxyl-terminated.

2. The method of claim 1 , wherein the mono- and di-substituted 1,3,5-hexahydro-1,3,5-triazine resins, respectively, have the following general formula:

wherein
X is H or CH 3 ,
R is CH 2 CH 2 —Y,
Y is —SR′, —NR′R or —NR′″;
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 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 of claim 1 , wherein the hydrolytically-stable, water-soluble polymerizable resin comprises at least one acrylamide group.

5. The method of claim 1 , wherein the hydrolytically-stable, water-soluble polymerizable resin comprises at least one inorganic acidic group.

6. The method of claim 1 , wherein the hydrolytically-stable, water-soluble polymerizable resin comprises at least one imidazolium group.

7. The method of claim 1 , wherein the hydrolytically-stable, water-soluble polymerizable resin comprises at least one imidazole group.

8. The method of claim 1 further comprising adding a phosphoric acid to the Michael donor of the mono- and di-substituted 1,3,5-hexahydro-1,3,5-triazine resin after the step of reacting the 1,3,5-hexahydro-1,3,5-triazine moiety with the Michael donor.

9. A method of forming a hydrolytically-stable, water-soluble polymerizable resin containing a 1,3,5-hexahydro-1,3,5-triazine moiety, the method comprising:
reacting the 1,3,5-hexahydro-1,3,5-triazine moiety in the presence of a Michael donor under conditions selected to yield mono-substituted and di-substituted 1,3,5-hexahydro-1,3,5-triazine resin present in a combined amount that is greater than a combined amount of tri-substituted 1,3,5-hexahydro-1,3,5-triazine and unreacted 1,3,5-hexahydro-1,3,5-triazine moiety;
wherein the Michael donor is imidazole.

10. The method of claim 9 further comprising converting the imidazole of the mono- and di-substituted 1,3,5-hexahydro-1,3,5-triazine resin to an imidazolium after the step of reacting the 1,3,5-hexahydro-1,3,5-triazine moiety with the Michael donor.

11. The method of claim 10 , wherein the step of converting the imidazole of the mono- and di-substituted 1,3,5-hexahydro-1,3,5-triazine resin to an imidazolium comprises reacting the mono- and di-substituted 1,3,5-hexahydro-1,3,5-triazine resin with bromohexane.

12. The method of claim 10 , wherein the step of converting the imidazole of the mono- and di-substituted 1,3,5-hexahydro-1,3,5-triazine resin to an imidazolium comprises reacting the mono- and di-substituted 1,3,5-hexahydro-1,3,5-triazine resin with bromododecane.

13. A method of forming a hydrolytically-stable, water-soluble polymerizable resin containing a 1,3,5-hexahydro-1,3,5-triazine moiety, the method comprising:
reacting the 1,3,5-hexahydro-1,3,5-triazine moiety in the presence of a Michael donor under conditions selected to yield mono-substituted and di-substituted 1,3,5-hexahydro-1,3,5-triazine resin present in a combined amount that is greater than a combined amount of tri-substituted 1,3,5-hexahydro-1,3,5-triazine and unreacted 1,3,5-hexahydro-1,3,5-triazine moiety;
wherein the Michael donor is a thiol.

14. The method of claim 13 , wherein the mono- and di-substituted 1,3,5-hexahydro-1,3,5-triazine resins, respectively, have the following general formula:

wherein
X is H or CH 3 ,
R is CH 2 CH 2 —Y,
Y is —SR′; and
R′ is a linear or branched linear alkyl having 1 to 18 carbon atoms with or without functional groups.

15. The method of claim 14 , wherein R′ is of the general form R′—Z m , wherein m=1-3 and Z═—OH, —SH, —COOH, COOR′, —OPO(OH) 2 , —OPO(OR′)(OH), —PO(OH) 2 , —PO(OR′)(OH),
—OSO 2 (OH), aromatics, or substituted aromatics.

16. The method of claim 9 , wherein the mono- and di-substituted 1,3,5-hexahydro-1,3,5-triazine resins, respectively, have the following general formula:

wherein
X is H or CH 3 ,
R is CH 2 CH 2 —Y, and
Y is imidazole.

17. The method of claim 9 , wherein the hydrolytically-stable, water-soluble polymerizable resin comprises at least one acrylamide group.

Assignees

• 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

• C07F9/65583

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

• C07F9/6521

  Six-membered rings · CPC title

• C07D251/04 Primary

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