Polymeric adhesive for anchoring compliant materials to another surface
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.
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.