# US 2016/0256362 A1 · Stabilized Calcium Phosphate and Methods of Forming Same

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- Number: US 2016/0256362 A1
- Document ID: US20160256362A1
- Status: Published application
- Kind: A1
- Application number: 14/638,289
- Filed: 2015-03-04
- Published: 2016-09-08
- Earliest claimed: 2015-03-04
- Assignees: Modern Ideas LLC
- Applicants: Modern Ideas LLC
- Inventors: Sunny Skaria; Kenneth Berk
- Web page: https://patentgrep.com/patent/US20160256362A1

## CPC

- A61K 6/838: Phosphorus compounds, e.g. apatite
- A61K 6/20: Protective coatings for natural or artificial teeth, e.g. sealings, dye coatings or varnish
- A61K 6/62: Photochemical radical initiators
- A61K 6/69: Medicaments
- A61K 6/71: Fillers
- A61K 6/74: comprising phosphorus-containing compounds
- A61K 6/77: Glass
- A61K 6/887: Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- B05D 5/061: {Special surface effect}
- C01B 25/32: Phosphates of magnesium, calcium, strontium, or barium
- C09J 4/00: Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16}
- C08F 222/1065: {of alcohol terminated (poly)urethanes, e.g. urethane(meth)acrylates}
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- B05D: PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL (conveying articles or workpieces through baths of liquid B65G, e.g. B65G49/02)
- C01B: NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; {METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C}
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## Abstract

A method of forming a stabilized calcium phosphate moiety for use in dental or biomedical applications includes providing a solution or dispersion including a calcium salt and reacting an organic phosphate having a polymerizable methacrylate or vinyl group with the solution or dispersion in order to form the calcium phosphate moiety having at least one pendant polymerizable group and at least one organic functional group, which may be the same group. A polymerizable composite system having a stabilized calcium phosphate formed according to the method is also provided.

## Claims

### Claim 1

A method of forming a stabilized calcium phosphate for use in dental or biomedical applications, the method comprising:
providing a solution or dispersion including a calcium salt; and
reacting an organic phosphate having a polymerizable methacrylate or vinyl group with the solution or dispersion in order to form a calcium phosphate moiety having at least one pendant polymerizable group and at least one organic functional group.

### Claim 2 (depends on 1)

The method of claim 1, wherein the at least one pendant polymerizable group and the at least one organic functional group are the same group.

### Claim 3 (depends on 1)

The method of claim 1, wherein the calcium salt includes calcium chloride, calcium hydroxide, calcium nitrate, or a combination thereof.

### Claim 4 (depends on 1)

The method of claim 1, wherein the organic phosphate having the polymerizable methacrylate or vinyl group includes bis[2-(methacryloyloxy)ethyl] phosphate, methacryloxy ethyl phosphate, glycerol dimethacrylate phosphate, glycerol monomethacrylate phosphate, triethyleneglycol methacrylate phosphate, methacryloyloxy propyl phosphate, methacryloyloxy hexyl phosphate, vinyl phosphonic acid, allyl phosphonic acid, polyethylene glycol methcrylate phosphate, methacrylated aminomethyl phosphonic acid, methacrylate esters of glycerol phosphate, polycaprolactone methacrylate phosphate, or a combination thereof.

### Claim 5 (depends on 1)

The method of claim 1, further comprising adding one or more inorganic phosphate sources to the organic phosphate to form a mixture, wherein the reacting includes reacting the mixture with the solution or dispersion in order to form the calcium phosphate moiety.

### Claim 6 (depends on 4)

The method of claim 4, wherein the one or more inorganic phosphate sources includes phosphoric acid or its salt, ammonium phosphate, pyrophosphoric acid or its salt, or a combination thereof.

### Claim 7 (depends on 5)

The method of claim 5, wherein the phosphoric acid or its salt includes sodium salt of phosphoric acid.

### Claim 8 (depends on 1)

The method of claim 1, wherein the solution includes the calcium salt solubilized or dispersed in deionized water.

### Claim 9 (depends on 1)

The method of claim 1, wherein reacting the organic phosphate with the solution includes hydrolyzing the polymerizable methacrylate in order to form the calcium phosphate moiety.

### Claim 10 (depends on 1)

Stabilized calcium phosphate formed according to the method of claim 1.

### Claim 11 (depends on 1)

A polymerizable composite system for use in dental or biomedical applications, the system comprising:
stabilized calcium phosphate formed according to the method of claim 1; and
one or more monomers selected from the group consisting of acidic monomers, hydrophilic monomers, hydrophobic monomers, and combinations thereof.

### Claim 12 (depends on 11)

The polymerizable composite system of claim 11, wherein the one or more monomers includes urethane dimethacrylate, bis[2-(methacryloyloxy)ethyl] phosphate, 1,6 hexamethylene dimethacrylate, trimethylol propane triacrylate, hydroxyethyl methacrylate, polyethylene glycol methacrylate, triethylene glycol dimethacrylate, polyethylene glycol dimethacrylate, polylactic acid methacrylate, polycaprolactone methacrylate, bisphenol A glycidyl methacrylate, bisphenol A glycidyl diacrylate, bisphenol A ethoxylate dimethacrylate, bisphenol A dimethacrylate, bisphenol A diglycidyl ether or a combination thereof.

### Claim 13 (depends on 11)

The polymerizable composite system of claim 11, further comprising one or more polymers, oligomers, or a combination thereof.

### Claim 14 (depends on 13)

The polymerizable composite system of claim 13, wherein the one or more polymers and/or oligomers includes oligomeric polybutadiene diurethane dimethacrylate.

### Claim 15 (depends on 11)

The polymerizable composite system of claim 11, further comprising a photoinitiator system.

### Claim 16 (depends on 15)

The polymerizable composite system of claim 15, wherein the photoinitiator system includes camphorquinone and an amine or a triphosphene oxide.

### Claim 17 (depends on 11)

The polymerizable composite system of claim 11, further comprising a non-reactive filler.

### Claim 18 (depends on 17)

The polymerizable composite system of claim 17, wherein the non-reactive filler includes silica, barium glass, strontium glass, quartz, barium sulfate or combinations thereof.

### Claim 19 (depends on 11)

The polymerizable composite system of claim 11, further comprising a self-curing system having a reducing agent and an oxidizing agent.

### Claim 20 (depends on 11)

The polymerizable composite system of claim 11, further comprising a dual cure system.