IP Library Granted Patent US 12,139,574
Granted Patent B2
US 12,139,574 · App. 18/364,242 · Granted Nov 12, 2024

Polymeric adhesive for anchoring compliant materials to another surface

Inventors: Lampros Kourtis (Cambridge, MA); David Myung (Santa Clara, CA); Daniel Chang (Danville, CA); Bing Yu (Berkeley, CA); Timothy Sun (Berkeley, CA); Michael J. Jaasma (San Francisco, CA); Vernon Hartdegen (Collierville, TN)
Assignee: Hyalex Orthopaedics, Inc.
C08G18/6229A61F2/30A61K47/32A61L24/001A61L24/0015A61L24/043A61L24/06A61M5/19B65D85/70C08G18/3206C08G18/4854C08G18/6511C08G18/6705C08G18/728C08G81/024C08L33/08C08L33/12C09J4/06C09J133/14C09J135/02F01D5/082F01D11/001F01D11/025A61B17/56A61L2300/406A61L2430/24F05D2240/57F05D2260/14
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Quick Facts
Patent No.
US 12,139,574
App. No.
18/364,242
Granted
Nov 12, 2024
Kind
B2
Abstract

Methods, compositions, and kits for adhering polymers and other materials to another material, and in particular to bone or bone-like structures or surfaces. A composition of matter includes a urethane dimethacrylate-methyl methacrylate copolymer with a plurality of first polymer regions based on urethane dimethacrylate and a plurality of second polymer regions based on methyl methacrylate. The method includes placing an orthopedic joint implant having an attachment surface in a joint space, applying a first non-urethane-containing precursor, a second urethane-containing precursor, and a initiator to the attachment surface; contacting the first and second precursors and the initiator with the joint surface; and copolymerizing the first and second precursors and forming an adhesive copolymer and attaching the implant to the joint.

Claims (26)

1. A device comprising:

a polymeric implant;

at least one of a metal and a ceramic material; and

a copolymer adapted to adhere the polymeric implant to the metal or ceramic material, wherein the copolymer is formed from

(i) a first precursor comprising a first ethylenically unsaturated group,

(ii) a second precursor comprising a second ethylenically unsaturated group, and

(iii) a free-radical initiator adapted to initiate a covalent bond between the first ethylenically unsaturated group and the second ethylenically unsaturated group to thereby form a copolymer.

2. The device of claim 1 , wherein the second precursor is a macromonomer or oligomer containing acrylic end groups.

3. The device of claim 2 , wherein the second precursor is a urethane-containing precursor.

4. The device of claim 3 , wherein the second precursor includes a urethane dimethacrylate monomer.

5. The device of claim 4 , wherein the second precursor comprises a soft segment formed from polybutadiene, polyethylene oxide (PEO), hydroxy terminated butadiene, hydroxybutyl terminated polydimethylsiloxane (PDMS), hydroxyl terminated polyisobutylene, poly (1,6 hexyl 1,2 ethyl carbonate), polycarbonate, polyethylene adipate, polyhexamethylene carbonate glycol, polypropylene oxide (PPO), polytetramethylene adipate, poly(dimethylsiloxane), poly(tetramethylene oxide) (PTMO), or a mixture thereof.

6. The device of claim 1 , wherein the polymeric implant is an orthopedic joint implant comprising a polyurethane IPN or a polyurethane semi-IPN.

7. The device of claim 6 , wherein the polymeric implant is an orthopedic joint implant comprising a polyether urethane IPN or a polyether urethane semi-IPN.

8. The device of claim 1 , further comprising a thermal inhibitor.

9. A method of adhering a polymeric implant to a metal or ceramic material comprising: copolymerizing a mixture containing a first precursor comprising a first ethylenically unsaturated group, a second precursor comprising a second ethylenically unsaturated end group, and a free-radical initiator to form an adhesive copolymer.

10. The method of claim 9 , wherein the second precursor is a macromonomer or oligomer containing acrylic end groups.

11. The method of claim 10 , wherein the second precursor is a urethane-containing precursor.

12. The method of claim 11 , wherein the second precursor includes a urethane dimethacrylate monomer.

13. The method of claim 12 , wherein the second precursor comprises a soft segment formed from polybutadiene, polyethylene oxide (PEO), hydroxy terminated butadiene, hydroxybutyl terminated polydimethylsiloxane (PDMS), hydroxyl terminated polyisobutylene, poly (1,6 hexyl 1,2 ethyl carbonate), polycarbonate, polyethylene adipate, polyhexamethylene carbonate glycol, polypropylene oxide (PPO), polytetramethylene adipate, poly(dimethylsiloxane), poly(tetramethylene oxide) (PTMO), or a mixture thereof.

14. The method of claim 9 , wherein the mixture further comprises an accelerator and an inhibitor.

15. The method of claim 9 , wherein the free-radical initiator comprises a photoinitiator, a thermal initiator, or both.

16. The method of claim 9 , wherein the free-radical initiator comprises a photoinitiator, and wherein the method comprises projecting light onto the photoinitiator thereby activating the photoinitiator and copolymerize the mixture to form the adhesive copolymer.

17. The method of claim 16 , wherein projecting light includes projecting a blue light or a UV light.

18. The method of claim 16 , wherein the polymeric implant includes a semi-transparent material, and projecting light includes projecting light through at least a portion of the semi-transparent material.

19. The method of claim 9 , wherein the copolymer includes a plurality of first structural units corresponding to the first precursor and a plurality of second structural units corresponding to the second precursor, and the method further comprises at least one of forming a crosslink between at least two of the first structural units, forming a crosslink between at least two of the second structural units, and forming a crosslink between a first structural unit and a second structural unit.

20. The method of claim 9 , further comprising placing a thermal inhibitor into the joint space.

Assignments (4)
SECURITY INTEREST Recorded Feb 7, 2024
From: HYALEX ORTHOPAEDICS, INC.
To: CUSTOMERS BANK
Reel/Frame 066406/0253 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 1, 2023
From: KOURTIS, LAMPROS; MYUNG, DAVID; CHANG, DANIEL; YU, BING; SUN, TIMOTHY; JAASMA, MICHAEL J.; HARTDEGEN, VERNON
To: BIOMIMEDICA, INC.
Reel/Frame 065731/0227 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 1, 2023
From: BIOMIMEDICA, INC.
To: HYALE SURGICAL, INC.
Reel/Frame 065731/0297 →
CHANGE OF NAME Recorded Dec 1, 2023
From: HYALE SURGICAL, INC.
To: HYALEX ORTHOPAEDICS, INC.
Reel/Frame 065741/0581 →
Continuity (8)
Continuation 17246819 · May 3, 2021
Continuation 16688351 · Nov 19, 2019
Continuation 15668547 · Aug 3, 2017
Continuation 14877884 · Oct 7, 2015
Continuation 13573788 · Oct 3, 2012
Provisional Application 61672203 · Jul 16, 2012
Provisional Application 61542740 · Oct 3, 2011
Related Publication 20240076438A1 · Mar 7, 2024