Bioabsorbable compounds and compositions containing them

1. A compound of the formula:

HO—R x R x R x R x -(A)-R x R x R x R x —OH

wherein A is a group derived from a dihydroxy compound with a molecular weight of less than about 1000; R can be the same or different at each occurrence and comprises groups derived from a compound selected from the group consisting of glycolide, lactide, p-dioxanone, trimethylene carbonate, and combinations thereof; and x can be the same or different at each occurrence and is 0 or 1, provided that at least two R groups are present.

2. A compound as in claim 1 wherein A is a group derived from a polyalkylene oxide.

3. A compound as in claim 1 wherein A is a group derived from a polyethylene glycol compound having a molecular weight selected from the group consisting of about 200, about 400, about 600 and about 900.

4. A compound as in claim 1 wherein at least one R group is derived from glycolide and at least one other R group is derived from lactide.

5. A compound as in claim 1 having a formula selected from the group consisting of:

HO—R-(A)-R—OH,

HO—R—R-(A)-R—R—OH, and

HO—R—R—R-(A)-R—R—R—OH.

6. A method comprising reacting a compound of claim 1 with a diisocyanate.

7. A method as in claim 6 wherein the diisocyanate is selected from the group consisting of aromatic diisocyanates, aliphatic diisocyanates, and alicyclic diisocyanates.

8. A method as in claim 6 wherein the diisocyanate is selected from the group consisting of 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 2,2′-diphenylmethane diisocyanate, 2,4′-diphenylmethane diisocyanate, 4,4′-diphenylmethane diisocyanate, diphenyldimethylmethane diisocyanate, dibenzyl diisocyanate, naphthylene diisocyanate, phenylene diisocyanate, xylylene diisocyanate, 4,4′-oxybis(phenylisocyanate), tetramethylxylylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, lysine diisocyanate, 2-methylpentane-1,5-diisocyanate, 3-methylpentane-1,5-diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, isophorone diisocyanate, cyclohexane diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated diphenylmethane diisocyanate, hydrogenated trimethylxylylene diisocyanate, and 2,4,6-trimethyl 1,3-phenylene diisocyanate.

9. A method comprising reacting a compound of claim 1 with a succinimidyl ester selected from the group consisting of sulfosuccinimidyl esters and N-hydroxysuccinimidyl esters.

10. A compound of the formula:

OCN—Z—HNCOO—R x R x R x R x -(A)-R x R x R x R x —OOCNH—Z—NCO

wherein Z is an aromatic or aliphatic group; A is a group derived from a polyalkylene oxide with a molecular weight of less than about 1000; R can be the same or different at each occurrence and comprises groups derived from absorbable monomers selected from the group consisting of glycolide, lactide, p-dioxanone, trimethylene carbonate, and combinations thereof; and x can be the same or different at each occurrence and is 0 or 1, provided that at least two R groups are present.

11. A compound as in claim 10 wherein Z is selected from the group consisting of toluene, diphenylmethane, diphenyldimethylmethane, dibenzyl, naphthylene, phenylene, xylylene, oxybisphenyl, tetramethylxylylene, tetramethylene, hexamethylene, lysine, methylpentane, trimethylhexamethylene, isophorone, cyclohexane, hydrogenated xylylene, hydrogenated diphenylmethane, hydrogenated trimethylxylylene, trimethylphenylene, and combinations thereof.

12. A compound as in claim 10 wherein A is a group derived from a polyethylene glycol having a molecular weight selected from the group consisting of about 200, about 400, about 600 and about 900.

13. A compound of the formula:

Y—R x R x R x R x -(A)-R x R x R x R x —Y  (II)

wherein Y is a group providing electrophilic or nucleophilic functionality; A is a group derived from a dihydroxy compound with a molecular weight of less than about 1000; R can be the same or different at each occurrence and comprises groups derived from absorbable monomers selected from the group consisting of glycolide, lactide, p-dioxanone, trimethylene carbonate, and combinations thereof; and x can be the same or different at each occurrence and is 0 or 1, provided that at least two R groups are present.

14. A compound as in claim 13 wherein Y includes a group selected from the group consisting of —NH 2 , —SH, —OH, —PH 2 , —CO—NH—NH 2 , —CO 2 N(COCH 2 ) 2 , —CO 2 H, —CHO, —CHOCH 2 , —N═C═O, —SO 2 —CH═CH 2 , —N(COCH) 2 , —S—S—(C 5 H 4 N), and combinations thereof.

15. A compound as in claim 13 wherein Y comprises an isocyanate.

16. A two part adhesive system comprising a first composition including a compound of claim 13 and a second composition comprising a multifunctional compound.

17. A two part adhesive system comprising a first composition comprising a compound of claim 13 and a second composition comprising a polyamine compound.

18. A method comprising

providing a dispensing device having at least two chambers and at least one outlet;

providing a first composition including a compound of claim 13 in a first chamber of the dispensing device;

providing a second composition including a multifunctional compound in a second chamber of the dispensing device; and

dispensing the first and second compositions through the at least one outlet of the dispensing device.

19. A method as in claim 18 wherein the second composition comprises a polyamine compound.

20. A method as in claim 18 further comprising the step of mixing the first and second compositions prior to dispensing.

21. A compound of the formula:

HO—R x R x R x R x -(A)-R x R x R x R x —OH

wherein A is a group derived from a dihydroxy compound with a molecular weight of less than about 1000; R can be the same or different at each occurrence and comprises groups derived from a compound selected from the group consisting of glycolide, lactide, p-dioxanone, trimethylene carbonate, and combinations thereof; x can be the same or different at each occurrence and is 0 or 1, provided that at least two R groups are present; and wherein the compound has a viscosity of from about 1,000 to about 500,000 centipoise at a temperature of from about 0° C. to about 40° C.