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Bioactive Dental Composites for Lasting Care

Introduction

Dental care has evolved significantly in recent years, yet traditional composites still present limitations when it comes to long-term durability and biological compatibility. Our patented bioactive dental composite offers a breakthrough in restorative dentistry, combining strength, aesthetics, and bioactivity to ensure longer-lasting restorations that promote oral health. This innovative material is designed to improve both patient outcomes and dental practice efficiency, offering a new gold standard in dental care.

Current Limitations in Dental Composites

While conventional dental composites provide an effective means for filling cavities and restoring damaged teeth, they often lack bioactivity. This means that although they fill a space, they do not actively contribute to the healing or health of the surrounding tissues. Over time, these composites may also degrade, requiring repairs or replacements that can be costly and inconvenient for both patients and practitioners.

Additionally, composites that do not bond well to the tooth structure can leave gaps where bacteria can enter, leading to further decay and complications. For the dental industry to move forward, bioactive materials that interact positively with oral tissues and enhance overall oral health are essential.

Why Choose Bioactive Dental Composites?

Our bioactive dental composite technology offers an innovative solution by combining the structural benefits of traditional composites with the bioactive properties that promote healing and remineralization. This composition actively releases beneficial ions, such as calcium and phosphate, which encourage the repair and regeneration of tooth tissue while helping to prevent further decay.

This bioactivity reduces the need for repeat dental procedures and promotes long-term patient satisfaction by strengthening the bond between the composite and the tooth. The material is also aesthetically pleasing, offering a natural appearance that blends seamlessly with the patient’s existing teeth.

For dental practitioners, this bioactive composite simplifies procedures, reducing the likelihood of recurrent issues and enhancing the quality of care provided. It’s a win for both dentists and patients, as it increases efficiency while improving oral health outcomes.

Key Benefits

  • Promotes Healing: Actively releases ions that support the regeneration and remineralization of tooth tissue.
  • Durable and Aesthetic: Combines long-lasting strength with a natural appearance.
  • Enhanced Bonding: Provides a better bond to the tooth structure, reducing the risk of future decay.
  • Patient Satisfaction: Improves outcomes and reduces the need for future dental repairs or replacements.

Empower Dental Health with Bioactive Composites

Licensing this bioactive dental composite technology offers dental practices a chance to lead with advanced materials that deliver superior results. By improving oral health, promoting healing, and ensuring long-lasting durability, these composites offer a pathway to better patient care and greater efficiency in dental procedures.

Please see terms and conditions
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.

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 (—PO3H2) 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, YbF3, 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:
Figure US10485735-20191126-C00013
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, NO2 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, NO2;
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:
Figure US10485735-20191126-C00014
wherein R is 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, NO2 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, NO2 or any combination thereof, or combination with any of —OH, —COOH, —PO3H2, 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, (CH2)p, (CF2)q, (CHF)q, C═O, C═C, C═C, benzyl, phenyl, F, Cl, Br, I, NO2, —COOH, —PO3H2 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, (CH2)p, (CF2)q, (CHF)q, C═O, C═C, C═C, benzyl, phenyl, F, Cl, Br, I, NO2, —COOH, —PO3H2 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:
Figure US10485735-20191126-C00015
wherein R is 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, NO2 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, (CH2)p, (CF2)q, (CHF)q, C═O, C═C, C═C, benzyl, phenyl, F, Cl, Br, I, NO2 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, (CH2)p, (CF2)q, (CHF)q, C═O, C═C, C═C, benzyl, phenyl, F, Cl, Br, I, NO2, —COOH, —PO3H2 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, (CH2)p, (CF2)q, (CHF)q, C═O, C═C, C═C, benzyl, phenyl, F, Cl, Br, I, NO2, —COOH, —PO3H2 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:
Figure US10485735-20191126-C00016
wherein R is 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, NO2 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, (CH2)p, (CF2)q, (CHF)q, C═O, C═C, C═C, benzyl, phenyl, F, Cl, Br, I, NO2 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 R1, R1′, R2, 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, NO2, —COOH, —PO3H2 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, (CH2)p, (CF2)q, (CHF)q, C═O, C═C, C═C, benzyl, phenyl, F, Cl, Br, I, NO2, —COOH, —PO3H2 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.
11. The dental composition of claim 1, wherein the monomer includes a calcium binding group selected from the group consisting of phosphonic, phosphoryl, carboxylic, sulfonic, hydroxyl, amino, as well as their salt, and combination or mixtures thereof.
12. The dental composition of claim 1, wherein the hydrolytically stable resin is effective to resist hydrolysis.
13. The dental composition of claim 1, wherein the bioactive filler has similar chemical composition with tooth, including calcium, or phosphate, or fluoride or combination and mixtures thereof, thus the calcium and phosphate in saliva can remineralize on the filler or composite.
14. The dental composition of claim 1, wherein the coupling agent includes a polymerizable double bond and a calcium binding group selected from the group consisting of a phosphorus group, a carboxylic acid, an amino group, a hydroxyl group, a sulfonic group, and/or their salt form.

15. The dental com-position of claim 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 the structure the general structure:
Figure US10485735-20191126-C00017
wherein R is selected from the group consisting of O, S, N, H, (CH2)p, (CF2)q, or 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 X′ are independently selected from the group consisting of CH2, O, S, or N; where the number of a orb can independently be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10;
wherein the phosphorous group can be replaced by carboxylic, sulfonic, hydroxyl or amine groups; wherein the number of phosphonic group and C═C double bonds can be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10.
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Title

Compositions and methods for bioactive dental composites

Inventor(s)

Tongxin Wang, Lawrence C. Chow

Assignee(s)

Howard University

Patent #

10485735

Patent Date

November 26, 2019

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