Surgical adhesive systems for hard body tissues

• US 4,626,310 A
• Filed: 05/10/1985
• Issued: 12/02/1986
• Est. Priority Date: 02/10/1982
• Status: Expired due to Term

• Current Assignee: Henkel KGaA (Henkel AG & Co KGaA)
• Original Assignee: Henkel KGaA (Henkel AG & Co KGaA)
• Inventors: Ritter, Wolfgang
• Primary Examiner(s): Gallagher, John J.
• Application Number:
  US06/732,801
• Time in Patent Office: 571 Days
• Field of Search: 526/318.3
• US Class Current: 156/307.3
• CPC Class Codes: A61F 2/28 Bones joints A61F2/30
• CPC Class Codes: A61L 27/16 obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: C08F 299/04 from polyesters
• CPC Class Codes: C08L 33/06 of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical

Abstract

Surgical adhesive systems for the bonding of hard body tissues which contain as a polymerization initiating starter an organoboron compound and a resorbable (meth)acrylate component which is liquid to solid at room temperature and which consists of (meth)-acrylic acid esters with (meth)-acrylate groups on polyester oligomer chains from hydroxycarboxylic acids, preferably having 2 (meth)-acrylate groups in the α, ω positions on the oligomer chains, and wherein the polyester oligomers are preferably formed from monohydroxymonocarboxylic acids.

Claims

1. A method of bonding hard body tissues to each other or to a metal or to a synthetic material comprising the steps of:

(A) applying to one or both surfaces to be joined together a surgical bonding system comprising;

(a) a polymerization initiating starter component which contains at least one organoboron compound; and

(b) a polymerizable adhesive component which contains at least one resorbable (meth)-acrylate compound which is a (meth)-acrylic acid ester having more than one (meth)-acrylate group on a polyester oligomer chain that contains hydroxy-carboxylic acid segments; and

(B) joining together said surfaces.

2. A method in accordance with claim 1 wherein components (a) and (b) are mixed together before application.

3. A method in accordance with claim 1 wherein component (a) is applied first to at least one of the surfaces to be joined together and thereafter component (b) is applied to at least one of the surfaces to be joined together.

4. A method in accordance with claim 1 wherein the hard body tissues are bones.

5. A two-component surgical bonding system for the bonding of hard body tissues which comprises

(a) a polymerization initiating starter component which contains at least one organoboron compound;

and

(b) a polymerization adhesive component which contains at least one resorbable (meth)-acrylate compound which is a (meth)-acrylic acid ester having more than one (meth) acrylate group on a polyester oligomer chain that contains hydroxycarboxylic acid segments.

6. A surgical bonding system in accordance with claim 5 wherein at least one (meth)-acrylate group in the resorbable (meth)-acrylate compound is on a terminal position of the polyester oligomer chain.

7. A surgical bonding system in accordance with claim 5 wherein the resorbable (meth)-acrylate compound contains a (meth)-acrylate group in both the α

and the ω

position of the polyester oligomer chain.

8. A surgical bonding system in accordance with claim 5 wherein each hydroxycarboxylic acid segment in the polyester oligomer chain of the resorbable (meth)-acrylate compound contains from 2 to 10 carbon atoms.

9. A surgical bonding system in accordance with claim 5 wherein each hydroxycarboxylic acid segment contains from 2 to 6 carbon atoms.

10. A surgical bonding system in accordance with claim 8 wherein the hydroxycarboxylic acid segments are formed from at least one of the following acids:

glycolic acid, lactic acid, hydroxypropionic acid, hydroxybutyric acid, and hydroxybenzoic acid.

11. A surgical bonding system in accordance with claim 5 wherein the polyester oligomer chain in the resorbable (meth)-acrylate compound has a mean molecular weight in the range of about 200 to about 600.

12. A surgical bonding system in accordance with claim 11 wherein the polyester oligomer chain has a mean molecular weight in the range of about 300 to about 500.

13. A surgical bonding system in accordance with claim 5 wherein the resorbable (meth)-acrylate compound also contains at least one moiety derived from the following:

a difunctional alcohol, and a difunctional carboxylic acid or a functionally reactive derivative thereof.

14. A surgical bonding system in accordance with claim 13 wherein a mixture of a monofunctional compound and a difunctional compound is employed in the formation of the (meth)-acrylate compound, and wherein the monofunctional compound is used in quantities not over 50 mole percent of said mixture said monofunctional compound being a monofunctional alcohol, a monofunctional carboxylic acid or functionally reactive derivative thereof, or a monofunctional amine.

15. A surgical bonding system in accordance with claim 14 wherein the monofunctional compound is used in quantities not over 10 mole percent of said mixture.

16. A surgical bonding system in accordance with claim 5 wherein the resorbable (meth)-acrylate compound has a viscosity at room temperature of from about 2000 to about 70,000 mPas.

17. A surgical bonding system in accordance with claim 16 wherein the viscosity at room temperature is from about 3,000 to about 50,000 mPas.

18. A surgical bonding system in accordance with claim 5 wherein the starter component (a) does not self-ignite when exposed to air yet will initiate polymerization of polymerizable adhesive component (b) at mammalian body temperatures when exposed to air.

19. A surgical bonding system in accordance with claim 18 wherein the organoboron compound in starter component (a) contains at least one substituent group selected from the group consisting of alkyl and aryl groups, and which can also optionally contain at least one B-H bond.

20. A surgical bonding system in accordance with claim 19 wherein the starter component (a) contains at least one alkyl boron compound selected from the group consisting of a trialkyl boron compound and an alkyl boron hydride compound.

21. A surgical bonding system in accordance with claim 5 wherein polymerization initiating starter component (a) contains at least one of the following:

(i) a homogeneous mixture of an organic oligomer or polymer, and at least one organoboron compound which is activated by exposure to air and is compatible with polymerizable adhesive component (b) and is inert toward the organic oligomer or polymer;

(ii) at least one polymeric organoboron compound which has, on a stable polymer matrix, boron hydride groups or organoboron groups, or a mixture of such groups, which are stable in the presence of oxygen; and

(iii) at least one boronalkyl compound which contains boron hydride groups, or organoboron groups, or a combination thereof, on a fatty acid or fatty alcohol ester.

22. A surgical bonding system in accordance with claim 21 wherein in the homogeneous mixture in (i) the organic oligomer or polymer is a polymer based on a derivative of (meth)-acrylic acid.

23. A surgical bonding system in accordance with claim 22 wherein the derivative of (meth)-acrylic acid is an ester or amide thereof.

24. A two component surgical bonding system for the bonding of hard body tissues which comprises

(a) a polymerization initiating starter component which contains at least one organoboron compound;

and

(b) a polymerization adhesive component which contains at least one resorbable (meth)-acrylate compound which is a (meth)-acrylic acid ester having a (meth)-acrylate group on a polyester oligomer chain that contains hydroxycarboxylic acid segments and which also contains a moiety derived from a monocarboxylic acid or functionally reactive derivative thereof.

25. A two component surgical bonding system in accordance with claim 24 wherein the (meth)-acrylate group is obtained by reaction of the terminal carboxy group of the polyester oligomer chain with the glycidyl ester of (meth)-acrylic acid.