Polymeric adhesive for anchoring compliant materials to another surface

• US 20130103157A1
• Filed: 10/03/2012
• Published: 04/25/2013
• Est. Priority Date: 10/03/2011
• Status: Abandoned Application

• Current Assignee: Biomimedica, Inc
• Original Assignee: Biomimedica, Inc
• Inventors: Kourtis, Lampros, Myung, David, Chang, Daniel, Jaasma, Michael J., Hartdegen, Vernon, Yu, Bing, Sun, Timothy
• Application Number:
  US13/573,788
• Publication Number:
  US 20130103157A1
• Time in Patent Office: Days
• US Class Current: 623/18.11
• CPC Class Codes: A61B 17/56 Surgical instruments or methods for treatment of bones or joints; Devices specially adapted therefor
• CPC Class Codes: A61F 2/30 Joints
• CPC Class Codes: A61K 47/32 Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers , poly(meth)acrylates, or polyvinyl pyrrolidone
• CPC Class Codes: A61L 2300/406 Antibiotics
• CPC Class Codes: A61L 24/001 Use of materials characterised by their function or physical properties
• CPC Class Codes: A61L 24/0015 Medicaments; Biocides
• CPC Class Codes: A61L 24/043 Mixtures of macromolecular materials
• CPC Class Codes: A61L 24/06 obtained by reactions only involving carbon-to-carbon unsaturated bonds A61L24/043, A61L24/046 take precedence
• CPC Class Codes: A61L 2430/24 for joint reconstruction
• CPC Class Codes: A61M 5/19 having more than one chamber , e.g. including a manifold coupling two parallelly aligned syringes through separate channels to a common discharge assembly surgical glue applicators A61B17/00491
• CPC Class Codes: B65D 85/70 for materials not otherwise provided for
• CPC Class Codes: C08F 220/14 Methyl esters , e.g. methyl (meth)acrylate
• CPC Class Codes: C08F 220/343 in the form of urethane links
• CPC Class Codes: C08G 18/3206 aliphatic
• CPC Class Codes: C08G 18/4854 Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
• CPC Class Codes: C08G 18/6229 Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
• CPC Class Codes: C08G 18/6511 compounds of group C08G18/3203
• CPC Class Codes: C08G 18/6705 Unsaturated polymers not provided for in the groups C08G18/671, C08G18/6795, C08G18/68 or C08G18/69
• CPC Class Codes: C08G 18/728 Polymerisation products of compounds having carbon-to-carbon unsaturated bonds and having isocyanate or isothiocyanate groups or groups forming isocyanate or isothiocyanate groups
• CPC Class Codes: C08G 81/024 Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G
• CPC Class Codes: C08L 33/08 : Homopolymers or copolymers of acrylic acid esters
• CPC Class Codes: C08L 33/12 : Homopolymers or copolymers of methyl methacrylate
• CPC Class Codes: C09J 133/14 : of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
• CPC Class Codes: C09J 135/02 : Homopolymers or copolymers of esters C09J135/06, C09J135/08 take precedence
• CPC Class Codes: C09J 4/06 : Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
• CPC Class Codes: F01D 11/001 : for sealing space between stator blade and rotor
• CPC Class Codes: F01D 11/025 : Seal clearance control; Floating assembly; Adaptation means to differential thermal dilatations
• CPC Class Codes: F01D 5/082 : on the side of the rotor disc
• CPC Class Codes: F05D 2240/57 : Leaf seals
• CPC Class Codes: F05D 2260/14 : Preswirling

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

1. A composition of matter comprising a urethane dimethacrylate-methyl methacrylate copolymer comprising a plurality of first polymer regions based on urethane dimethacrylate and a plurality of second polymer regions based on methyl methacrylate.

2. The composition of claim 1 wherein the first polymer regions based on urethane dimethacrylate comprise about 60%-99% (w/w) of the copolymer and the second polymer regions based on methyl methacrylate comprise about 1%-40% (w/w) of the copolymer.

3. The composition of claim 1 wherein the first polymer regions based on urethane dimethacrylate comprise about 60%-80% (w/w) of the copolymer and the second polymer regions based on methyl methacrylate comprise from about 20%-40% (w/w) of the copolymer.

4. The composition of claim 1 wherein the first polymer regions based on urethane dimethacrylate comprise soft segments based on poly(tetramethyl) glycol, the soft segments having a molecular weight between about 100 Da and about 5000 Da.

5. The composition of claim 1 wherein the urethane dimethacrylate-methyl methacrylate copolymer defines a compressive modulus between about 30 MPa and about 2000 MPa.

6. The composition of claim 1 wherein the urethane dimethacrylate-methyl methacrylate copolymer defines a tensile modulus between about 30 MPa and 2000 MPa.

7. The composition of claim 1 wherein the urethane dimethacrylate-methyl methacrylate copolymer defines a failure strain between about 25% and about 200%.

8. The composition of claim 1 further comprising a radiopaque material.

9. A composition of matter comprising:

from about 60% (w/w) to about 99% (w/w) urethane dimethacrylate monomer;

from about 1% (w/w) to about 40% (w/w) methyl methacrylate monomer;

an initiator;

an accelerator; and

an inhibitor.

10. The composition of claim 9 wherein the composition comprises between 0% (w/w) to about 1% (w/w) initiator, between 0% (w/w) to about 1% (w/w) accelerator;

and between 0% (w/w) to about 0.1% (w/w) inhibitor.

11. The composition of matter of claim 9 comprising from about 60% (w/w) to about 80% (w/w) urethane dimethacrylate monomer and from about 20% (w/w) to about 40% (w/w) methyl methacrylate monomer.

12. The composition of matter of claim 9 further comprising from about 1% (w/w) to about 70% (w/w) poly(methyl methacrylate) powder.

13. The composition of claim 9 wherein the initiator comprises a photoinitiator.

14. The composition of claim 9 wherein the initiator comprises camphorquinone.

15. The composition of claim 9 wherein the initiator comprises a thermal initiator.

16. The composition of claim 9 wherein the initiator comprises a thermal initiator and a photoinitiator.

17. The composition of claim 9 wherein the initiator comprises benzoyl peroxide.

18. The composition of claim 9 wherein the accelerator comprises N,N-dimethyl-p-toluidine.

19. The composition of claim 9 wherein the inhibitor comprises hydroquinone.

20. The composition of claim 9 further comprising an additive configured to prevent an infection.

21. The composition of claim 9 further comprising an antibiotic.

22. The composition of claim 9 further comprising a radiopaque material.

23. The composition of claim 9 wherein the composition defines a viscosity between about 1 Pa·

s and about 5000 Pa·

s.

24. An adhesive kit comprising:

a first reservoir comprising a first mixture comprising at least one of a urethane dimethacrylate monomer and a methyl methacrylate monomer;

at least one of a photoinitiator and a thermal initiator; and

an inhibitor;

a second reservoir comprising a second mixture comprising at least one of a urethane dimethacrylate monomer and a methyl methacrylate monomer; and

an accelerator; and

an instruction for use;

wherein at least one of the first reservoir and the second reservoir comprises a urethane dimethacrylate monomer and at least one of the first reservoir and the second reservoir comprises a methyl methacrylate monomer.

25. The adhesive kit of claim 24 wherein both the first reservoir and the second reservoir comprise a urethane dimethacrylate monomer and a methyl methacrylate monomer.

26. The adhesive kit of claim 24 wherein the second reservoir further comprises an inhibitor.

27. The adhesive kit of claim 24 further comprising poly(methyl methacrylate).

28. The adhesive kit of claim 24 further comprising a third reservoir comprising a poly(methyl methacrylate) powder.

29. The adhesive kit of claim 28 wherein the first mixture, the second mixture and the poly(methyl methacrylate) define a component weight, and a weight of the poly(methyl methacrylate) powder comprises from about 1% to about 70% of the component weight.

30. The adhesive kit of claim 24 further comprising a polystyrene.

31. The adhesive kit of claim 24 further comprising a photoinitiator and a thermal initiator.

32. The adhesive kit of claim 24 wherein the first reservoir comprises a first chamber in a syringe and the second reservoir comprises a second chamber in the syringe, wherein the syringe is configured to combine the first mixture with the second mixture to create an adhesive mixture.

33. The adhesive kit of claim 32 further comprising a nozzle connected with the syringe configured to dispense the adhesive mixture.

34. The adhesive kit of claim 24 wherein the first reservoir and the second reservoir each comprise from about 60% (w/w) to about 80% (w/w) urethane dimethacrylate monomer.

35. The adhesive kit of claim 24 wherein the first reservoir and the second reservoir each comprise from about 20% (w/w) to about 40% (w/w) methyl methacrylate.

36. The adhesive kit of claim 24 wherein the at least one initiator comprises a photoinitiator comprising between 0% (w/w) and about 1% (w/w) camphorquinone.

37. The adhesive kit of claim 24 wherein the at least one initiator comprises a thermal initiator comprising between 0% (w/w) and about 1% (w/w) benzoyl peroxide.

38. The adhesive kit of claim 24 wherein the accelerator comprises between 0% (w/w) and about 1% (w/w) N,N-dimethyl-p-toluidine.

39. The adhesive kit of claim 24 wherein the inhibitor comprises between 0% (w/w) an about 0.1% (w/w) hydroquinone.

40. The adhesive kit of claim 24 further comprising an additive configured to prevent an infection.

41. The adhesive kit of claim 24 further comprising an antibiotic.

42. The adhesive kit of claim 24 further comprising a radiopaque material.

43. The adhesive kit of claim 24 wherein the first mixture defines a viscosity between about 1 Pa·

s and 5000 Pa·

s.

44. A method of attaching an orthopedic joint implant to a joint comprising:

placing an orthopedic joint implant in a joint space, the orthopedic joint implant having a bearing surface and an attachment surface adapted to attach the orthopedic joint implant to a joint surface of a joint;

applying a first non-urethane-containing precursor, a second urethane-containing precursor, and a first initiator to the attachment surface of the orthopedic joint implant;

contacting the first precursor, the second precursor, and the first initiator with the joint surface; and

copolymerizing the first non-urethane-containing precursor with the second urethane-containing precursor and forming an adhesive copolymer comprising a non-urethane-containing portion based on the first precursor and a urethane-containing portion based on the second precursor to thereby attach the orthopedic joint implant to the joint.

45. The method of claim 44 wherein the first precursor comprises a first chemical functional group, the second precursor comprises a second chemical functional group, and the first initiator comprises a free-radical initiator, and copolymerizing comprises forming a covalent bond between the first functional group and the second functional group in response to the free-radical initiator.

46. The method of claim 44 above wherein the first precursor comprises a first ethylenically unsaturated group and the second precursor comprises a second ethylenically unsaturated group and copolymerizing comprises forming a covalent bond between the first ethylenically unsaturated group and the second ethylenically unsaturated group in response to a free-radical initiator.

47. The method of claim 44 above wherein the first precursor comprises first precursor molecules each comprising an acrylic group, and copolymerizing comprises covalently bonding a plurality of first precursor molecules through the acrylic groups.

48. The method of claim 44 above wherein the second precursor comprises second precursor molecules comprising two acrylic groups, and copolymerizing comprises covalently bonding a plurality of second precursor molecules through the acrylic groups.

49. The method of claim 44 above wherein the copolymer comprises a plurality of first structural units corresponding to the first non-urethane-containing precursor and a plurality of second structural units corresponding to the second urethane-containing precursor, 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.

50. The method of claim 44 wherein the first precursor comprises a methyl methacrylate monomer and the second precursor comprises a urethane dimethacrylate monomer, and copolymerizing comprises forming a urethane dimethacrylate-methyl methacrylate copolymer.

51. The method of claim 44 further comprising mixing the first non-urethane-containing precursor, the second urethane-containing precursor and the first initiator prior to the applying step.

52. The method of claim 44 wherein the first initiator comprises a photoinitiator, the method further comprising projecting light on the photoinitiator to activate the photoinitiator;

and copolymerizing the first non-urethane-containing precursor with the second urethane-containing precursor and forming an adhesive copolymer to thereby attach the orthopedic joint implant to the joint in response to the activated photoinitiator.

53. The method of claim 52 wherein copolymerizing the first precursor with the second precursor comprises projecting light for a time period less than about 2 minutes.

54. The method of claim 52 wherein projecting light comprises projecting light discontinuously.

55. The method of claim 52 wherein projecting light comprises projecting a blue light.

56. The method of claim 52 wherein projecting light comprises projecting a UV light.

57. The method of claim 52 wherein the orthopedic joint implant comprises a semi-transparent material, and projecting the light comprises project the light through at least a portion of the semi-transparent material.

58. The method of claim 44 further comprising placing a thermal inhibitor in the joint space.

59. The method of claim 44 wherein the first initiator comprises a thermal initiator further comprising:

polymerizing a portion of the first non-urethane-containing precursor in response to the thermal initiator to form a non-urethane-containing oligomeric molecule.

60. The method of claim 44 further wherein the first initiator comprises a thermal initiator, the method further comprising:

polymerizing a portion of the first non-urethane-containing precursor in response to the thermal initiator to form a non-urethane-containing oligomeric molecule;

wherein copolymerizing comprises copolymerizing the non-urethane-containing oligomeric molecule with the second precursor in response to the thermal initiator.

61. The method of claim 44 wherein the first initiator comprises a photoinitator, further comprising:

placing a second initiator comprising a thermal initiator in the joint space; and

projecting light on the photoinitiator to activate the photoinitiator;

wherein copolymerizing comprises copolymerizing a first portion of the first non-urethane-containing precursor with a first portion of the second urethane-containing precursor in response to the activated photoinitiator and copolymerizing a second portion of the first non-urethane-containing precursor with a second portion of the second urethane-containing precursor in response to the thermal initiator, thereby forming an adhesive copolymer comprising a non-urethane-containing portion based on the first precursor and a urethane-containing portion based on the second precursor.

62. The method of claim 44 further comprising placing a reaction accelerator in the joint space.

63. The method of claim 44 further comprising priming the attachment surface of the implant with an organic solution prior to the contacting step.

64. The method of claim 44 wherein comprising priming the attachment surface of the implant with an acetone solution prior to the contacting step.

65. The method of claim 44 further comprising swelling the orthopedic joint implant with a solvent prior to the applying step.

66. The method of claim 44 further comprising forming an IPN or semi-IPN between the adhesive copolymer and the orthopedic joint implant.

67. The method of claim 44 further comprising removing a biological material from the joint prior to the contacting step.

68. The method of claim 44 further comprising interdigitating the adhesive copolymer in at least one of a feature on the attachment surface of the orthopedic joint implant and a feature on the joint surface.

69. The method of claim 44 wherein interdigitating comprises interdigitating the adhesive copolymer with at least one of a bump, a depression, a groove, a pore, and a space.

70. The method of claim 44 further comprising interdigitating the adhesive copolymer with cancellous bone.

71. The method of claim 44 wherein the attachment surface of the orthopedic joint implant comprises a polyurethane IPN or polyurethane semi-IPN, the method further comprising forming a non-covalent interaction between the adhesive copolymer and the polyurethane IPN or polyurethane semi-IPN.

72. The method of claim 71 wherein forming a non-covalent interaction comprises forming at least one of an absorption interaction, a crystallite formation, an entanglement, a hydrogen bond, a hydrophobic interaction, an ionic interaction, a pi-bond stacking, and a van der Waals interaction.

73. The method of claim 44 wherein the orthopedic joint implant comprises a water-swellable IPN or a water-swellable semi-IPN, the method further comprising interpenetrating a portion of the adhesive copolymer with the water-swellable IPN or water-swellable semi-IPN.

74. The method of claim 44 wherein the orthopedic joint implant comprises an IPN or semi-IPN having a first phase domain, the method further comprising choosing a second precursor comprising a second phase domain configured to interfacially adhere to the first phase domain.

75. The method of claim 74 further comprising forming a chemical bond between the first phase domain and the second phase domain.

76. The method of claim 74 further comprising forming a hydrogen bond between the first phase domain and the second phase domain.

77. The method of claim 44 wherein the orthopedic joint implant comprises an IPN or semi-IPN based on a polyether urethane comprising a hard segment based on methylene diphenyl diisocyanate, the method further comprising choosing a second precursor comprising a hard segment based on methylene diphenyl diisocyanate.

78. The method of claim 44 wherein the orthopedic joint implant comprises an IPN or semi-IPN based on a polyether urethane comprising a soft segment based on poly(tetramethyl)glycol, the method further comprising choosing a second precursor comprising a soft segment based on poly(tetramethyl)glycol.

79. A method of attaching a first portion of a bone to a second portion of a bone, comprising:

applying a first non-urethane containing precursor, a second urethane-containing precursor, and a first initiator to the attachment surface of the orthopedic joint implant; and

copolymerizing the first non-urethane-containing precursor with the second urethane-containing precursor and forming an adhesive copolymer to thereby attach the first portion of the bone to the second portion of the bone.

80. The method of claim 79 wherein forming an adhesive comprises forming a biodegradable adhesive.

81. The method of claim 79 wherein applying a second urethane-containing precursor comprises applying a precursor based on a lysine diisocyanate.