IP Library Granted Patent US 11,760,830
Granted Patent B2
US 11,760,830 · App. 17/246,819 · Granted Sep 19, 2023

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 11,760,830
App. No.
17/246,819
Granted
Sep 19, 2023
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 (18)

1. A device comprising: (a) a polymeric implant, (b) a metal or ceramic material, and (c) a copolymer adhering the polymeric implant to the metal or ceramic material, wherein the copolymer is formed from (i) a first precursor comprising a methyl methacrylate monomer and (ii) a second precursor, wherein the second precursor is a macromonomer or oligomer containing ethylenically unsaturated end groups.

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. A method of adhering a polymeric implant to a metal or ceramic material comprising copolymerizing a mixture containing a first precursor comprising a methyl methacrylate monomer, a second precursor, and an initiator to form an adhesive copolymer, wherein the second precursor is a macromonomer or oligomer containing ethylenically unsaturated end groups.

9. The method of claim 8 , wherein the second precursor is a macromonomer or oligomer containing acrylic end groups.

10. The method of claim 9 , wherein the second precursor is a urethane-containing precursor.

11. The method of claim 10 , wherein the second precursor includes a urethane dimethacrylate monomer.

12. The method of claim 11 , 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.

13. The method of claim 8 , wherein the mixture further comprises an accelerator and an inhibitor.

14. The method of claim 8 , wherein the initiator comprises a free-radical initiator.

15. The method of claim 14 , wherein the free-radical initiator comprises a photoinitiator, a thermal initiator, or both.

16. The method of claim 14 , 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.

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 Jul 9, 2021
From: KOURTIS, LAMPROS; MYUNG, DAVID; CHANG, DANIEL; YU, BING; SUN, TIMOTHY; JAASMA, MICHAEL J.; HARTDEGEN, VERNON
To: BIOMIMEDICA, INC.
Reel/Frame 056803/0747 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 9, 2021
From: BIOMIMEDICA, INC.
To: HYALE SURGICAL, INC.
Reel/Frame 056803/0952 →
CHANGE OF NAME Recorded Jul 9, 2021
From: HYALE SURGICAL, INC.
To: HYALEX ORTHOPAEDICS, INC.
Reel/Frame 056813/0314 →
Continuity (7)
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 20210332179A1 · Oct 28, 2021