Compositions and methods for adhesion to surfaces

1. A method of joining two or more bones, bone fragments, or bone segments with an injectable adhesive composition, the method comprising injecting the adhesive composition in a fluid state onto or into the bones, bone fragments, or bone segments to be joined;

wherein the adhesive composition comprises an organic phosphate compound, a multivalent metal salt selected from tetracalcium phosphate or tricalcium phosphate, and an aqueous medium, the injectable adhesive composition comprising about 10% to about 35% aqueous medium to provide for a viscosity between 100 cP and 10,000 cP when in the fluid state;

the multivalent metal salt is provided as a powder; and

the mean particle size of the powder particles is between 0.005 mm and 0.150 mm;

thereby joining two or more bones, bone fragments, or bone segments.

2. The method of claim 1 , further comprising preparing the bone, bone fragment, or bone segment prior to injecting the adhesive composition.

3. The method of claim 2 , wherein the preparing comprises milling, drilling, or reaming.

4. The method of claim 1 , wherein the adhesive composition hardens over time into a cement-like state in about 30 minutes.

5. The method of claim 1 , further comprising applying a compressive force to the bones, bone fragments, or bone segments to be joined prior to, during, and/or after injecting the adhesive composition.

6. The method of claim 4 , wherein the adhesive composition exhibits an adhesive strength in the cement-like state of between 100 kPa and 12,000 kPa.

7. The method of claim 1 , wherein multivalent metal salt is present within the adhesive composition in an amount between 30% and 75% (w/w) of the total weight.

8. The method of claim 1 , wherein the multivalent metal salt is tricalcium phosphate.

9. The method of claim 8 , wherein the tricalcium phosphate comprises α-tricalcium phosphate or β-tricalcium phosphate.

10. The method of claim 1 , wherein the multivalent metal salt is tetracalcium phosphate.

11. The method of claim 1 , wherein the organic phosphate compound is a compound of Formula (I) or a salt thereof:

wherein:

L is O, S, NH, or CH 2 ;

each of R 1a and R 1b is independently H, optionally substituted alkyl, or optionally substituted aryl;

R 2 is H, NR 4a R 4b , C(O)R 5 , or C(O)OR 5 ;

R 3 is H, optionally substituted alkyl, or optionally substituted aryl;

each of R 4a and R 4b is independently H, C(O)R 6 , or optionally substituted alkyl;

R 5 is H, optionally substituted alkyl, or optionally substituted aryl;

R 6 is optionally substituted alkyl or optionally substituted aryl; and

each of x and y is independently 0, 1, 2, or 3.

12. The method of claim 1 , wherein the organic phosphate compound comprises phosphoserine.

13. The method of claim 1 , wherein the organic phosphate compound is present within the adhesive composition in an amount between 10% and 90% (w/w) of the total weight.

14. The method of claim 1 , wherein the aqueous medium comprises water, saliva, saline, serum, plasma, or blood.

15. The method of claim 1 , wherein the adhesive composition further comprises an additive.

16. The method of claim 15 , wherein the additive comprises a salt, filler, formulation base, viscosity modifier, abrasive, coloring agent, flavoring agent, or polymer.

17. The method of claim 16 , wherein the polymer comprises poly(L-lactide), poly(D,L-lactide), polyglycolide, poly(ε-caprolactone), poly(teramethylglycolic-acid), poly(dioxanone), poly(hydroxybutyrate), poly(hydroxyvalerate), poly(lactide-co-glycolide), poly(glycolide-co-trimethylene carbonate), poly(glycolide-co-caprolactone), poly(glycolide-co-dioxanone-co-trimethylene-carbonate), poly(tetramethylglycolic-acid-co-dioxanone-co-trimethylenecarbonate), poly(glycolide-co-caprolactone-co-lactide-co-trimethylene-carbonate), poly(hydroxybutyrate-co-hydroxyvalerate), poly(methylmethacrylate), poly(acrylate), polyamines, polyamides, polyimidazoles, poly(vinyl-pyrrolidone), collagen, silk, chitosan, hyaluronic acid, gelatin, or a mixture thereof.

18. The method of claim 1 , wherein the mean particle size of the powder particles is between 0.060 mm and 0.150 mm.