Compositions and methods for bioactive dental composites

Patent metadata

Field	Value
Publication number	US-10485735-B2
Application number	US-201414895771-A
Country	US
Kind code	B2
Filing date	Jun 6, 2014
Priority date	Jun 7, 2013
Publication date	Nov 26, 2019
Grant date	Nov 26, 2019

Abstract

Described herein are compositions and methods which produce hydrolytically stable resin monomers, bioactive fillers, phosphorus coupling agent and surface coating method, which can be combined to produce new generation dental composites; compositions comprising the same, as well as methods of making and using the same are also described.

First claim

What is claimed is:

1. A dental composition comprising:
a hydrolytically stable resin, the hydrolytically stable resin including a monomer lacking an ester or amide bond between a polymerizable double bond;
a bioactive filler; and
a coupling agent, the coupling agent lacking a hydrolysable ester bond, wherein the coupling agent has FA (fluoroapatite) or calcium phosphate binding groups, comprising phosphorus binding groups selected from the group consisting of phosphonic acid group (—PO 3 H 2 ) as well as its salt and combinations and mixtures thereof.

2. The dental composition according to claim 1 , wherein the bioactive filler includes at least one material selected from the group consisting of FA (fluorapatite), HA (hydroapatite), FHA (fluorhydroxyapatite), ACP (amorphous calcium phosphate), TCP (tricalcium phosphate), TTCP (tetracalcium phosphate), DCP (dicalcium phosphate), MCP (monocalcium phosphate), bioglass, quartz, glass, silicate, Ba/Sr/silicate glass, metal oxides, YbF 3 , and mixtures thereof.

3. The dental composition of claim 1 , wherein the filler can be used as major filler or minor filler.

4. The dental composition of claim 1 , wherein the coupling agent includes a material selected from the group consisting of phosphorus group, carboxylic acid group, hydroxyl group, amino group, sulfonic acid group, as well as their salt, and combination and mixtures thereof.

5. A dental composition comprising:
a hydrolytically stable resin, the hydrolytically stable resin including a monomer lacking an ester or amide bond between a polymerizable double bond;
a bioactive filleri and
a coupling agent, the coupling agent lacking a hydrolysable ester bond, wherein the coupling agent has the structure the general structure:

wherein the number of phosphonic groups and C═C double bonds independently can be 1, 2, 3, 4, 5, 6, 7, 8, 9, and/or 10,
wherein R, R1 and/ or R2 are each independently selected from the group consisting of B, C, Si, O, S, N, P, H, (CH2) p , (CF2) q , (CHF) q , C═O, C═C, C═C, benzyl, phenyl, F, Cl, Br, I, NO 2 and any combination thereof, where p and q are independently 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20;
wherein X, and/or X′ are each independently selected from the group consisting of B, C, Si, O, S, N, P, H, (CH2) p , (CF2) q , (CHF) q , C═O, C═C, C═C, benzyl, phenyl, F, Cl, Br, I, NO 2 ;
wherein the number of a and b can each independently be 1, 2, 3, 4, 5, 6, 7, 8, 9, and/ or 10;
wherein the phosphorus group can be replaced by carboxylic, sulfonic, hydroxyl or amine group.

6. The dental composition of claim 1 , wherein the filler can be coated after preparation of filler or with preferable method to combine surface coating and ball milling into one single step.

7. The dental composition of claim 1 , wherein the monomer has greater water resistance than BisGMA and TEGDMA.

8. The dental composition of claim 1 , wherein the monomer has the general structure:

wherein R is selected from the group consisting of B, C, Si, O, S, N, P, H, (CH 2 ) p , (CF 2 ) q , (CHF) q , C═O, C═C, C═C, benzyl, phenyl, F, Cl, Br, I, NO 2 or any combination thereof, where p and q can each independently be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20;
wherein Y, Z, Y′ and/ or Z′ are each independently selected from the group consisting of B, C, Si, O, S, N, P, H, (CH2)p, (CF2)q, (CHF)q, C═O, C═C, C═C, benzyl, phenyl, F, Cl, Br, I, NO 2 or any combination thereof, or combination with any of —OH, —COOH, —PO 3 H 2 , where p and q can each independently be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20;
wherein R1, R1′, R2, and/or R2′ are each independently selected from the group consisting of B, C, Si, O, S, N, P, H, (CH 2 ) p , (CF 2 ) q , (CHF) q , C═O, C═C, C═C, benzyl, phenyl, F, Cl, Br, I, NO 2 , —COOH, —PO 3 H 2 or any combination thereof, where p and q can each independently be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20; and
wherein R3, R4, R3′, and/or R4′ are each independently selected from the group consisting of B, C, Si, O, S, N, P, H, (CH 2 ) p , (CF 2 ) q , (CHF) q , C═O, C═C, C═C, benzyl, phenyl, F, Cl, Br, I, NO 2 , —COOH, —PO 3 H 2 or any combination thereof, where p and q can each independently be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20.

9. The dental composition of claim 1 , wherein the monomer has the general structure:

wherein R is selected from the group consisting of B, C, Si, O, S, N, P, H, (CH 2 ) p , (CF 2 ) q , (CHF) q , C═O, C═C, C═C, benzyl, phenyl, F, Cl, Br, I, NO 2 and any combination thereof, where p and q can each independently be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20;
wherein X, Y, X′ and/or Y′ are each independently selected from the group consisting of B, C, Si, O, S, N, P, H, (CH 2 ) p , (CF 2 ) q , (CHF) q , C═O, C═C, C═C, benzyl, phenyl, F, Cl, Br, I, NO 2 and any combination thereof, where p and q can each independently be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20;
wherein R1, R1′, R2, and/or R2′ are each independently selected from the group consisting of B, C, Si, O, S, N, P, H, (CH 2 ) p , (CF 2 ) q , (CHF) q , C═O, C═C, C═C, benzyl, phenyl, F, Cl, Br, I, NO 2 , —COOH, —PO 3 H 2 and any combination thereof, where p and q can each independently be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20; and
wherein R3, R4, R3′, and/or R4′ are each independently selected from the group consisting of B, C, Si, O, S, N, P, H, (CH 2 ) p , (CF 2 ) q , (CHF) q , C═O, C═C, C═C, benzyl, phenyl, F, Cl, Br, I, NO 2 , —COOH, —PO 3 H 2 and any combination thereof, where p and q can each independently be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20.

10. The dental composition of claim 1 , wherein the monomer has the general structure:

wherein R is selected from the group consisting of B, C, Si, O, S, N, P, H, (CH 2 ) p , (CF 2 ) q , (CHF) q , C═O, C═C, C═C, benzyl, phenyl, F, Cl, Br, I, NO 2 or any combination thereof, where p and q can each independently be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20;
wherein X, Y, Z, X′, Y′, and/or Z′ are each independently selected from the group consisting of B, C, Si, O, S, N, P, H, (CH 2 ) p , (CF 2 ) q , (CHF) q , C═O, C═C, C═C, benzyl, phenyl, F, Cl, Br, I, NO 2 or any combination thereof, where p and q can each independently be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20;
wherein R 1 , R1′, R2, and/or R2′ are each independently selected from the group consisting of B, C, Si, O, S, N, P, H, (CH 2 ) p , (CF 2 ) q , (CHF) q , C═O, C═C, C═C, benzyl, phenyl, F, Cl, Br, I, NO 2 , —COOH, —PO 3 H 2 or any combination thereof, where p and q can each independently be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20; and
wherein R3, R4, R3′, and/or R4′ are each independently selected from the group consisting of B, C, Si, O, S, N, P, H, (CH 2 ) p , (CF 2 ) q , (CHF) q , C═O, C═C, C═C, benzyl, phenyl, F, Cl, Br, I, NO 2 , —COOH, —

Assignees

• Wang Tongxin
• Chow Lawrence C
• Univ Howard

Inventors

• Wang Tongxin
• Chow Lawrence C

Classifications

• A61K6/887

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

• A61K6/75 Primary

  Apatite · CPC title

• A61K6/0085 Primary

  Human Necessities · mapped topic

• C08L33/08

  Homopolymers or copolymers of acrylic acid esters · CPC title

• C08L33/10

  Homopolymers or copolymers of methacrylic acid esters · CPC title