Polymeric adhesive for anchoring compliant materials to another surface

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.

What is claimed is: 
     
         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.