Tetra calcium phosphate based organophosphorus compositions and methods
Compositions and methods of their use to adhere a variety of materials together are disclosed herein. The compositions include at least tetra calcium phosphate, an effective amount of a compound that is structurally similar to phosphoserine, and can be mixed with an aqueous solution. The compositions provide adhesive and cohesive strength in both wet and dry environments and exhibit significant bond strength upon curing.
1. A method of repairing a hard surface comprising the steps of:
mixing a composition comprising an effective amount of tetra calcium phosphate and a compound of the formula
where A is O, CH 2 , or S; R is H, NH 2 , NHCO(CH 2 ) t CH 3 where t is 0 to 2, NH(CH 2 ) x CH 3 where x is 0 to 3, NR1R2 where R1 is (CH 2 ) y CH 3 and R2 is (CH 2 ) y CH 3 where y is 0 to 2, (CH 2 ) z CH 3 where z is 0 to 3, where m is 0 to 1, and where n is 0 to 3 and wherein the compound is present in an amount from about 10% to about 90% by weight based on the combined weight of the tetra calcium phosphate and the compound,
with sufficient aqueous medium to create a mixture;
applying the mixture to the hard surface to be repaired; and
allowing the mixture to cure.
2. The method of claim 1 wherein the hard surface is bone.
3. The method of claim 2 wherein the mixture is applied to a void in the bone to fill the void.
4. The method of claim 1 wherein the compound is present in an amount from about 15% to about 50% by weight based on the combined weight of the of the tetra calcium phosphate and the compound.
5. The method of claim 1 wherein the compound is present in an amount of about 20% to about 40% by weight based on the combined weight of the of the tetra calcium phosphate and the compound.
6. The method of claim 1 wherein the compound is selected from the group consisting of phosphoserine, carboxy ethyl phosphonate, phoshonoacetic acid, and mixtures thereof.
7. The method of claim 1 wherein R is H, or NH 2 .
8. The method of claim 1 wherein the compound is phosphoserine.
9. The method of claim 1 wherein the composition has a mean particle size of less than 1000 microns.
10. The method of claim 1 wherein the aqueous medium is a blood based product.
11. The method of claim 1 wherein the aqueous medium is water.
12. The method of claim 1 wherein the composition further includes an additive.
13. The method of claim 1 wherein the mixture has a tacky state for up to 12 minutes after mixing with the aqueous medium.
14. The method of claim 13 wherein the mixture during the tacky state has a separation strength in the range of about 10 kPa to about 250 kPa after mixing with the aqueous medium.
15. The method of claim 1 wherein the mixture composition has a putty state for up to 15 minutes after mixing with the aqueous medium.
16. A method of repairing bone structure comprising the steps of:
applying a composition comprising an effective amount of tetra calcium phosphate and a compound of the formula
where A is 0, CH 2 , or S; R is H, NH 2 , NHCO(CH 2 ) 1 CH 3 where t is 0 to 2, NH(CH 2 ) x CH 3 where x is 0 to 3, NR1R2 where R1 is (CH 2 ) y CH 3 and R2 is (CH 2 ) y CH 3 where y is 0 to 2, (CH 2 ) z CH 3 where z is 0 to 3, where m is 0 to 1, and where n is 0 to 3 and wherein the compound is present in an amount from about 10% to about 90% by weight based on the combined weight of the tetra calcium phosphate and the compound directly to the bone structure to be repaired; and
allowing the composition to harden by combining in situ with aqueous based bodily fluids.
17. The method of claim 16 wherein the compound is present in an amount from about 15% to about 50% by weight based on the weight of the of the tetra calcium phosphate and the compound.
18. The method of claim 16 wherein the compound is present in an amount of about 20% to about 40% by weight based on the combined weight of the of the tetra calcium phosphate and the compound.
19. The method of claim 16 wherein the compound is selected from the group consisting of phosphoserine, carboxy ethyl phosphonate, phoshonoacetic acid, and mixtures thereof.
20. The method of claim 16 wherein R is H, or NH 2 .
21. The method of claim 16 wherein the compound is phosphoserine.
22. The method of claim 16 wherein the composition has a mean particle size of less than 1000 microns.
23. The method of claim 16 wherein the composition further includes an additive.
24. A method of joining bone to another material comprising the steps of:
mixing a composition comprising an effective amount of tetra calcium phosphate and a compound of the formula
where A is 0, CH 2 , or S; R is H, NH 2 , NHCO(CH 2 ) t CH 3 where t is 0 to 2, NH(CH 2 ) x CH 3 where x is 0 to 3, NR1R2 where R1 is (CH 2 ) y CH 3 and R2 is (CH 2 ) y CH 3 where y is 0 to 2, (CH 2 ) z CH 3 where z is 0 to 3, where m is 0 to 1, and where n is 0 to 3 and wherein the compound is present in an amount from about 10% to about 90% by weight based on the combined weight of the tetra calcium phosphate and the compound, with sufficient aqueous medium to create a mixture;
applying the mixture to a surface of the bone;
placing the surface of the bone into contact with a material to be joined to the bone; and
allowing the mixture to cure.
25. The method of claim 24 wherein the other material is a soft tissue.
26. The method of claim 24 wherein the other material is a metal.
27. The method of claim 24 wherein the other material is a ceramic.
28. The method of claim 24 wherein the other material is a bioglass.
29. The method of claim 24 wherein the other material is bone.
30. The method of claim 24 wherein the mixture is allowed to cure without the application of external pressure.
31. The method of claim 1 wherein the mixture has a tacky state for up to 4 minutes after mixing with the aqueous medium.
32. The method of claim 1 wherein the mixture has a tacky state for up to 2 minutes after mixing with the aqueous medium.
33. The method of claim 1 wherein the mixture composition has a putty state for up to 8 minutes after mixing with the aqueous medium.
34. The method of claim 1 wherein the mixture composition has a putty state for up to 5 minutes after mixing with the aqueous medium.
35. The method of claim 13 wherein the mixture during the tacky state has a separation strength in the range of about 50 kPa to about 150 kPa after mixing with the aqueous medium.