# US 8,771,719 B2 · Synthesis of a bone-polymer composite material > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,771,719 B2 - Document ID: US8771719B2 - Status: Granted - Kind: B2 - Application number: 10/639,912 - Filed: 2003-08-12 - Published: 2004-07-29 - Granted: 2014-07-08 - Earliest claimed: 2002-08-12 - Assignees: Warsaw Orthopedic, Inc. - Applicants: Lawrence A. Shimp; John M. Winterbottom; Todd M. Boyce; David Knaack - Inventors: Lawrence A. Shimp; John M. Winterbottom; Todd M. Boyce; David Knaack - Web page: https://patentgrep.com/patent/US8771719B2 ## CPC - A61L 27/48: with macromolecular fillers - A61L 27/3608: {Bone, e.g. demineralised bone matrix [DBM], bone powder} - A61L 27/46: with phosphorus-containing inorganic fillers - C08L 89/00: Compositions of proteins; Compositions of derivatives thereof - A61L 2430/02: for reconstruction of bones; weight-bearing implants - A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K) - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) ## Abstract A method of producing a bone-polymer composite. The method comprises the steps of providing a plurality of bone particles, combining the bone particles with a polymer precursor, and polymerizing the polymer precursor. ## Claims ### Claim 1 A composition, comprising: a plurality of bone particles having a surface modified with a silane coupling agent; wherein the bone particles are about 51% to about 75% by weight of the composition, or the bone particles are about 76% to about 99% by weight of the composition; and a polymer precursor selected from a monomer, and a prepolymer, wherein: when the polymer precursor is polymerized, at least a portion of the bone particles are covalently attached to the polymerized polymer precursor, at least a portion of the interstitial and vascular structure of the bone particles is infiltrated by the polymerized polymer precursor, or both and the composition comprises a polymer matrix having at least about 60% of the bone particles being elongated and randomly orientated in the polymer matrix and the polymer matrix comprises a biodegradable polyurethane. ### Claim 2 (depends on 1) The composition of claim 1 wherein at least a portion of the bone particles are covalently linked to the polymer precursor. ### Claim 3 (depends on 1) The composition of claim 1, wherein at least a portion of the interstitial and vascular structure of the bone particles are infiltrated with the polymer precursor. ### Claim 4 (depends on 1) The composition of claim 1, wherein the bone particles are selected from the group consisting of nondemineralized bone particles, demineralized bone particles, and mixtures thereof. ### Claim 5 (depends on 1) The composition of claim 1 wherein the bone particles are obtained from a member of the group consisting of cortical bone, cancellous bone, cortico-cancellous bone, and mixtures thereof. ### Claim 6 (depends on 1) The composition of claim 1, wherein the bone particles are obtained from a member of the group consisting of autogenous bone, allogenic bone, xenogeneic bone, and mixtures thereof. ### Claim 7 (depends on 1) The composition of claim 1 wherein the bone particles are about 51% to about 75% by weight of the composition. ### Claim 8 (depends on 1) The composition of claim 1, wherein the bone particles are about 76% to about 99% by weight of the composition. ### Claim 9 (depends on 1) The composition of claim 1, wherein the silane coupling agent comprises an active group that is incorporated into the polymerized polymer precursor. ### Claim 10 (depends on 9) The composition of claim 9, wherein the active group is monofunctional or multifunctional. ### Claim 11 (depends on 1) The composition of claim 1, wherein the surfaces of the bone particles are further modified with a moiety selected from the group consisting of a biomolecule, a small molecule, a bioactive agent, a non-biologically active material, an inorganic material, a mineral, and any combination of the above to the bone particles. ### Claim 12 (depends on 1) The composition of claim 1, wherein the silane coupling agent is derivatized modified with a moiety selected from the group consisting of a biomolecule, a small molecule, a bioactive agent, a non-biologically active material, an inorganic material, a mineral, and any combination of the above. ### Claim 13 (depends on 11) The composition of claim 11, wherein the moiety is incorporated into the polymerized polymer precursor and linked to the polymerized polymer precursor by a member of covalent interactions, non-covalent interactions, and any combination of the above. ### Claim 14 (depends on 1) The composition of claim 1 wherein the bone particles include exposed collagen fibers at the surface. ### Claim 15 (depends on 14) The composition of claim 14, wherein the exposed collagen fibers are frayed. ### Claim 16 (depends on 14) The composition of claim 14, wherein the exposed collagen fibers are cross-linked. ### Claim 17 (depends on 14) The composition of claim 14, wherein the exposed collagen fibers are derivatized with a moiety selected from the group consisting of a biomolecule, a small molecule, a bioactive agent, a non-biologically active material, an inorganic molecule, a mineral, and any combination of the above. ### Claim 18 (depends on 1) The composition of claim 1 wherein the bone particles comprise a coating of calcium phosphate. ### Claim 19 (depends on 1) The composition of claim 1, wherein the polymerized polymer precursor is a polymer comprising one or more of biodegradable, nonbiodegradable, co-polymers of biodegradable polymers, co-polymers of nonbiodegradable polymers, and co-polymers of biodegradable and non-biodegradable polymers. ### Claim 20 (depends on 19) The composition of claim 19, wherein the polymer further comprises one or more of poly(phosphoesters), polysulfones, polyfumarates, polyphosphazines, poly(alkylene oxides), poly(arylates), poly(anhydrides), poly(hydroxy acids), polyesters, poly(ortho esters), polycarbonates, poly(propylene fumerates), poly(caprolactones), polyamides, polyamino acids, polyacetals, polylactides, polyglycolides, poly(dioxanones), polyhydroxybutyrate, polyhydroxyvalyrate, poly(vinyl pyrrolidone), biodegradable polycyanoacrylates, polysaccharides, tyrosine-based polymers, poly(pyrrole), poly(aniline), poly(thiophene), polystyrene, nonbiodegradable polyurethanes, polyureas, poly(ethylene vinyl acetate), polypropylene, polymethacrylate, polyethylene, poly(ethylene oxide), and mixtures, adducts, and copolymers thereof. ### Claim 21 (depends on 1) The composition of claim 1, wherein the plurality of bone particles are compressed together in a predetermined shape. ### Claim 22 (depends on 21) The composition of claim 21, wherein the compressed particles have a void volume not greater than 32%. ### Claim 23 (depends on 21) The composition of claim 21, further comprising a member of a biocompatible binder, filler, fiber, plasticizer, biostatic/biocidal agent, surface active agent, biomolecule, small molecule, bioactive agent, and any combination of the above. ### Claim 24 (depends on 21) The composition of claim 21, wherein the shape is selected from a shape selected from the group consisting of a bone, a section of a bone, sheet, particle, sphere, strand, coiled strand, capillary network, film, fiber, mesh, plate, disk, cone, pin, screw, tube, cup, tooth, tooth root, strut, wedge, portion of wedge, cylinder, threaded cylinder, and rod. ### Claim 25 (depends on 12) The composition of claim 12, wherein the moiety is incorporated in the polymerized polymer precursor and linked to the polymerized polymer precursor by a member of covalent interactions, non-covalent interactions, and any combinations of the above. ### Claim 26 (depends on 1) The composite of claim 1, wherein the silane coupling agent comprises one or more of N-beta-(Aminoethyl)-gamma-aminopropylmethyldiethoxysilane, N-beta-(Aminoethyl)-gamma-aminopropyltrimethoxysilane, gamma-Aminopropylmethyldiethoxysilane, gamma-Aminopropyltriethoxysilane, gamma-Aminopropyltrimethoxysilane, Bis(3-triethoxysilylpropyl)tetrasulfide, gamma-Chloropropyltriethoxysilane, gamma-Chloropropyltrimethoxysilane, gamma-Glycidopropyltrimethoxysilane, gamma-Mercaptopropyltrimethoxysilane, gamma-Methacryloxypropyltrimethoxysilane, Methyltriacetoxysilane, Methyltrimethoxysilane, Methyl tris-(butanone oxime)Silane, Methyl Oximino Silane, Methyl tris-(methyl ethyl ketoximo)Silane, Phenyl tris-(butanone oxime)Silane, Tetraethoxysilane, Tetra(methyl ethyl ketoximo)Silane, Tetramethoxysilane, Vinyltriethoxysilane, Vinyltrimethoxysilne, Vinyl tris-(butanone oxime)Silane, Vinyl Oximino Silane, or Vinyl tris-(methyl ethyl ketoximo)Silane.