US20120289608A1 - Bone cement and a method for producing same - Google Patents

Bone cement and a method for producing same Download PDF

Info

Publication number
US20120289608A1
US20120289608A1 US13/499,348 US201013499348A US2012289608A1 US 20120289608 A1 US20120289608 A1 US 20120289608A1 US 201013499348 A US201013499348 A US 201013499348A US 2012289608 A1 US2012289608 A1 US 2012289608A1
Authority
US
United States
Prior art keywords
bone cement
component
particles
cured
biodegradable
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US13/499,348
Other languages
English (en)
Inventor
Christoph Sattig
Elvira Dingeldein
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Aap Biomaterials GmbH and Co KG
Original Assignee
Aap Biomaterials GmbH and Co KG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Aap Biomaterials GmbH and Co KG filed Critical Aap Biomaterials GmbH and Co KG
Assigned to AAP BIOMATERIALS GMBH reassignment AAP BIOMATERIALS GMBH ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: DINGELDEIN, ELVIRA, SATTIG, CHRISTOPH
Publication of US20120289608A1 publication Critical patent/US20120289608A1/en
Abandoned legal-status Critical Current

Links

Images

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
    • A61L24/001—Use of materials characterised by their function or physical properties
    • A61L24/0036—Porous materials, e.g. foams or sponges
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
    • A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
    • A61K6/891—Compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
    • A61L24/001—Use of materials characterised by their function or physical properties
    • A61L24/0042—Materials resorbable by the body
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
    • A61L24/0047—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material
    • A61L24/0073—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material with a macromolecular matrix
    • A61L24/0084—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material with a macromolecular matrix containing fillers of phosphorus-containing inorganic compounds, e.g. apatite
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/40—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material
    • A61L27/44—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material having a macromolecular matrix
    • A61L27/46—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material having a macromolecular matrix with phosphorus-containing inorganic fillers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L27/56—Porous materials, e.g. foams or sponges
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L27/58—Materials at least partially resorbable by the body
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
    • A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
    • A61L2300/406—Antibiotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61L2430/00—Materials or treatment for tissue regeneration
    • A61L2430/02—Materials or treatment for tissue regeneration for reconstruction of bones; weight-bearing implants

Definitions

  • the invention relates to a bone cement and a method for producing same.
  • bone cements based on calcium phosphate or calcium sulfate, for example, are known. After they are applied in each case, a sufficient initial stability can be achieved with these bone cements. Of course, the hardened material* is very brittle, so that a sufficient permanent stability cannot be achieved for many cases of application.
  • Calcium phosphates are also known. Of course, in the case of calcium phosphate-based bone cements, there is a softening of the material even after a short time, so that in many cases, defect sites cannot be stabilized sufficiently rapidly, particularly in elderly patients. *presumably based on calcium sulfate, but this is not stated in the German text.—Translator's note.
  • acrylic-based bone cements are generally used, and not only in elderly patients. These have the advantage of a high rigidity even after a brief hardening or curing.
  • a connective-tissue type of layer is formed around the implanted acrylic-based cement; bone material does not grow into the bone cement, but an acrylic-based bone cement is usually very well tolerated.
  • Acrylic-based bone cements generally cannot be degraded by the body. Therefore, attempts have been made to improve the biocompatibility of these types of cements, for example, by addition of hydroxyapatite. These types of additives for the most part, of course, are only accessible at the surface of the cement, predominantly surrounded by acrylic and for the most part are not resorbable. Finally, the known additive of calcium compounds can usually only improve the growth of tissue on the bone cement, but the quantity of accessible particles is usually not sufficient to achieve or to promote a new formation of bone in direct contact.
  • the invention relates to an acrylic-based bone cement, in which the named disadvantages of known acrylic-based bone cements will be reduced.
  • an object of the invention is to provide a bone cement that is at least partially biodegradable and therefore natural bone tissue can grow through it.
  • the bone cement will be able to be better adapted in its strength to the strength of natural bone, whereby, in particular, the danger of fractures in the vertebral region will be reduced.
  • the object of the invention will be achieved by a bone cement, a cured bone cement, as well as by a method for mixing bone cement according to one of the independent claims.
  • the invention relates to a bone cement that is provided particularly for inserting prostheses, but also for closing or filling bone defects, depending on the indication in each case.
  • the bone cement comprises at least one polymerizable hydrophobic component, at least one hydrophilic component and biodegradable particles.
  • the hydrophilic component preferably comprises water, the biodegradable particles forming a suspension in water.
  • the aqueous, hydrophilic component does not mix with the hydrophobic component, so that the biodegradable particles remain behind in the pores formed by the hydrophilic component.
  • the biodegradable particles are thus freely accessible.
  • At least 50, preferably at least 80% of the biodegradable particles are contained in the hydrophilic component. A large portion of the particles is thus freely accessible. Unlike known bone cements with biodegradable particles as an additive, the particles are not sealed by the polymer matrix.
  • the hydrophobic component comprises an acrylate monomer, in particular, an acrylate monomer being understood as a compound that can be polymerized into a polyacrylic.
  • the latter involves an acrylic-based bone cement.
  • it may involve an acrylic acid ester, in particular methyl methacrylate.
  • Monomers or oligomers from which polyacrylates form are sufficiently known and are hydrophobic, at least in the unhardened state, so that when they are combined with water, usually they do not produce dispersions with a fine distribution.
  • acrylate-based bone cements In the hardened or cured state, acrylate-based bone cements usually reduce their hydrophobic properties and can in fact absorb water up to several percent of their weight. According to the invention, the hydrophobic properties need only be present in the unhardened state; therefore, a dissolution or a fine dispersion of the two components does not occur.
  • At least partially open-pore regions which are first filled with the hydrophilic component, are formed by the hydrophilic component.
  • the biodegradable particles, which are preferably contained in the hydrophilic component are predominantly accumulated in the pores, so that after curing, an at least partially open-pore cured acrylic cement is present, the pores of which are occupied by biodegradable material.
  • the inventors could thus provide an acrylic-based bone cement, which can be interspersed with natural bone material after its application.
  • the inventors have discovered that the addition of a hydrophilic component, in particular the addition of water, reduces the E-modulus and simultaneously increases the yield strength at break. In this way, in vertebroplasty and kyphoplasty or related applications, the danger of fractures of both cured bone cement and adjacent bone material can be reduced.
  • biodegradable particles are preferably contained in the hydrophilic component.
  • biodegradable particles are added together with an acrylic-based bone cement powder or, in fact, with the acrylate monomer, since the biodegradable particles would predominantly migrate into the hydrophilic component based on their properties alone.
  • the hydrophilic component preferably comprises water and a calcium carbonate, sulfate and/or phosphate.
  • Carbonate, sulfate, phosphate in this case are understood in the broadest sense, thus all compounds of sulfur, phosphorus and carbonates with calcium.
  • the hydrophilic component comprises hydroxyapatite.
  • the biodegradable material in particular the hydroxyapatite, is preferably present in nanoparticulate form, thus with an average particle size of less than 100 nm.
  • larger particles in particular having a size of up to 20 ⁇ m can also be used.
  • the particles are preferably present in a suspension, which, when mixed with the hydrophobic component, mostly sticks together and thus thread-like structures are formed, which lead to an interconnected structure.
  • a viscous suspension of nanoparticles has these properties to a particular extent.
  • nanoparticulate hydroxyapatite is also particularly suitable for accelerating the ingrowth of bone tissue.
  • the hydrophilic component contains a substance that starts a polymerization of the hydrophobic component, in particular an initiator.
  • the bone cement can be provided as a two-component system, in which the initiator is contained in the hydrophilic component.
  • dibenzoyl peroxide can be used as an initiator.
  • the hydrophobic component contains polymer particles.
  • bone cement is provided as a combination of monomer and powder.
  • the mixed bone cement can be provided with a paste-like consistency.
  • the polymer particles are usually partially dissolved during the curing and are bound in the forming polymer matrix. Due to the fact that the complete volume need not be polymerized, heating is also reduced during the curing.
  • the hydrophilic component reduces the evolution of heat during curing of the bone cement according to the invention, which presents an additional advantage of the bone cement according to the invention.
  • the bone cement contains an x-ray contrast agent.
  • the x-ray contrast agent in this case can be contained in the hydrophilic component and/or in the hydrophobic component.
  • the bone cement contains a pharmaceutically active substance, in particular an antibiotic.
  • the antibiotic is preferably contained in the hydrophilic component.
  • the bone cement contains between 10 and 50% biodegradable material, in particular biodegradable particles, between 20 and 80% of the polymerizable hydrophobic component, optionally between 10 and 60% polymer particles and between 2 and 30% water (unless otherwise indicated, the data are always in weight %).
  • the invention relates to a bone cement, in particular having one or more of the above features, which comprises a polymer component as well as a liquid that is immiscible with the polymer component.
  • the liquid involves water in particular.
  • biodegradable particles are contained in the liquid that is immiscible with the polymer component.
  • the biodegradable particles are present as a suspension in water.
  • the polymer component particularly involves a monomer or a prepolymer that hardens into a polymer matrix.
  • the polymer component usually also comprises polymer particles that are mixed in during mixing with the monomer.
  • the polymer component is immiscible with the suspension in which the biodegradable particles are contained. Due to the inclusion of drops of the suspension in this case, pores are formed, in which the biodegradable particles are freely accessed.
  • the invention relates to a bone cement, comprising 25 to 80% polymeric bone cement powder, 5 to 30% water, 10 to 70% biodegradable particles, as well as a monomer and an initiator.
  • the invention relates to a cured bone cement, in particular a bone cement that is cured from the above-described bone cement.
  • the cured bone cement comprises a polymer backbone with open pores that are filled at least partially with biodegradable material.
  • it involves a cured acrylate-based bone cement, whose polymer backbone comprises an acrylate, in particular a polymethylmethacrylate.
  • an acrylate-based bone cement which has in the cured state an E-modulus of less than 4500 MPa, preferably less than 2000 MPa, and particularly preferred, less than 1600 MPa, can be provided by the invention.
  • the E-modulus is measured in the initially cured state after a curing time of approximately five hours by application of ISO5833:2002 Annex F.
  • the desired rigidity can be adjusted via the ratio of hydrophobic and hydrophilic components with the bone cement according to the invention.
  • the bone cement according to the invention is thus relatively soft for an acrylate-based bone cement, which reduces the danger of subsequent fractures after treatment of vertebral bodies.
  • the cured bone cement has a porosity between 5 and 90, preferably between 10 and 50, and particularly preferred between 10 and 35% referred to the polymer backbone.
  • porosity is understood to be the calculated porosity, in which closed pores are also included in the porosity.
  • the hydrophilic component and the biodegradable material, which is found in the hydrophilic component are not included in the porosity.
  • porosity is particularly understood to be the calculated porosity, for which the volume of the hydrophobic component from which the polymer backbone is formed, is placed in a ratio with the volume of the hydrophilic component.
  • the cured bone cement has an average pore size between 5 ⁇ m and 5 mm, preferably between 20 and 200 ⁇ m.
  • the pore size can be controlled, among other things, by selection of the mixing method. It is also conceivable to reduce the pore size by additives that reduce the surface tension of water.
  • the polymer backbone is at least partially composed of a cross-linked polymer.
  • polymer particles of a partially cross-linked polymer can be used for producing the bone cement. After adding the monomer, portions that are not cross-linked are partially dissolved and can serve as a connecting link to the polymer matrix forming as the monomer*. Thus, particles are not only embedded, but are cross-linked to the molecular plane. *sic; forming from the monomer?—Translator's note.
  • the invention relates to a method for producing bone cement, wherein a polymerizable hydrophobic component is mixed with a hydrophilic component and biodegradable material.
  • At least partially open-pore regions which are first filled with the hydrophilic component, are formed by the hydrophilic component, which by definition is immiscible with the hydrophobic component.
  • the biodegradable material is preferably added and mixed together with the hydrophilic component as a suspension, in particular as a paste.
  • the paste is highly viscous and essentially dimensionally stable, such as a curd or fresh cheese, for example.
  • the viscosity can amount to between 1 and 100,000 Pa ⁇ s.
  • a suspension containing nanoparticles that have been produced in the suspension such as nanoparticulate hydroxyapatite for example, 20 to 40% particles in the suspension lead to the desired consistency.
  • the particle concentration usually must be higher in order to obtain the desired consistency.
  • Precipitated material containing particles that are clearly larger than 100 nm can therefore make necessary a particle fraction of 60% or more in the suspension.
  • hydrophilic component is neither sedimented nor independently separated from the hydrophobic component. Therefore, a “street”-like structure remains at least partially, which is filled with a particle suspension.
  • the biodegradable particles are highly accessible and promote the ingrowth into the cured cement.
  • both the degree of porosity as well as the size of the pores, and within certain limits, also the appearance of the pores, particularly the pores formed as channels, can be determined in advance.
  • the hydrophilic component present as the suspension preferably has a viscosity that is similar to the remaining bone cement.
  • the components can be mixed with one another by means of a statistical mixer, which leads to particularly good results when two pastes are employed.
  • At least two pastes are employed, a first paste containing the polymerizable hydrophobic component and the second paste containing the biodegradable material, an initiator and water.
  • the bone cement according to the invention can thus be used as a two-component system.
  • the first paste is preferably mixed with an accelerator, which accelerates the polymerization.
  • Dimethyl-p-toluidine is used as the accelerator.
  • a pre-polymerized, partially cross-linked polymer for example in the form of a pearl polymer, after mixing with the monomer, leads to the partial dissolution of the polymer particles and the formation of long-chain polymers of the acrylate monomer is accelerated. Simultaneously, partially dissolved or dissolved-out components of the polymer particles lead to a thickening of the mixture to produce the desired viscosity.
  • hydroquinone can be added, which prevents a premature polymerization due to radical scavenging.
  • a polymerizable metal salt is used for producing the hydrophobic component.
  • zirconium (meth)acrylate or barium (meth)acrylate can be used.
  • a metal acrylate, particularly a zirconium or barium acrylate, is preferably formed from the metal salt due to the presence of acrylic acid or methacrylic acid.
  • Cross-links can be provided via an acrylate, in particular a metal acrylate, which can be well dissolved in the hydrophobic component due to the good shielding of the metal atom. Both butylals and methylacrylates can be used.
  • the acrylate can be produced as a particulate prepolymer from an acetate by addition of methacrylic acid.
  • the acrylate can be produced from zirconium acetate.
  • the acetate can be precipitated by means of methacrylic acid, and the zirconium acrylate that forms can be used for producing the hydrophobic component.
  • acrylates such as, for example, aluminum acrylate, magnesium acrylate and calcium acrylate, can be used.
  • an x-ray contrast agent can likewise be bound in the polymer matrix.
  • an x-ray contrast agent can likewise be bound in the polymer matrix.
  • titanium acrylate is also conceivable, in particular for the additional provision of an x-ray contrast agent.
  • a bone cement can be produced as follows, by way of example.
  • an acrylate-based bone cement composed of a monomer and a polymeric bone cement powder are mixed.
  • a bone cement paste is formed in this way, as it can be used according to the prior art.
  • Another paste that is composed of a suspension of finely dispersed, distributed particles of hydroxyapatite, calcium carbonate, calcium sulfate and/or calcium phosphate are mixed and combined with the bone cement in a suitable mixing device.
  • a concentrated suspension containing hydroxyapatite, calcium carbonate, calcium sulfate and/or calcium phosphate can also be mixed directly with the polymer particles of the acrylate-based bone cement and the monomer.
  • a paste composed of an aqueous phase and finely dispersed, distributed particles of hydroxyapatite, calcium carbonate, calcium sulfate and/or calcium phosphate and dibenzoyl peroxide is mixed with a second paste.
  • a pharmacologically effective substance [is added]* is added.
  • the second paste contains methyl(meth) acrylate and/or butyl acrylate as the monomer, dimethyl-p-toluidine as an accelerator and optionally, an x-ray contrast agent. Further, the second paste contains a partially cross-linked PMMA pearl polymer.
  • the two pastes are mixed by means of a suitable mixer with or without a statistical mixing element and can then be introduced into defect sites by means of a syringe or by hand.
  • a suitable mixer with or without a statistical mixing element and can then be introduced into defect sites by means of a syringe or by hand.
  • *Text given in brackets does not appear in the original German text, but is added for clarity.—Translator's note.
  • the PMMA contained in the pearl polymer partially dissolves out from the beads or the beads swell and the otherwise very thin fluid methyl methacrylate is thickened.
  • other polymers in particular PMMA polymers, dissolved or swollen polymers, can be mixed in.
  • FIGS. 1 and 2 show schematically the histological findings for the femoral condyles of a sheep, which were produced as follows.
  • a defect approximately 15 cm deep and 10 mm diameter was made by means of a drill in the medial femoral condyle of both hind limbs of a sheep, and on one side the defect was filled with conventional acrylate-based bone cement, and on the other side with a bone cement according to the invention.
  • the animal was euthanized three months after the surgery.
  • the condyles were sawed into slabs and stained bone sections were prepared.
  • FIG. 1 shows the defect site of the animal that was filled with conventional acrylate-based bone cement
  • FIG. 2 shows the defect site that was filled with a bone cement according to an example of embodiment of the invention.
  • circle 1 of the same size is superimposed on the two images.
  • This circle 1 could also symbolize an implant, for example. It can be recognized in FIG. 1 that between circle 1 and natural bone material 2 , a region 3 is present that is penetrated at most to a small extent by natural bone material. In FIG. 2 , the natural bone material 2 , in contrast, extends up to circle 1 .
  • FIG. 3 shows a flow chart of a schematically presented production or mixing method.
  • the bone cement is mixed from two components, a hydrophobic component 4 and a hydrophilic component 5 .
  • the hydrophobic component comprises a PMMA pearl polymer, methyl methacrylate, dimethyl-p-toluidine as an accelerator and a contrast agent.
  • the hydrophilic component comprises an aqueous suspension containing hydroxyapatite, calcium carbonate, calcium sulfate and, in addition, comprises dibenzoyl peroxide, which is added as an initiator for the polymerization.
  • the two components are mixed in a statistical mixer and can then be applied.
  • FIGS. 4 to 6 show SEM photomicrographs of a cured bone cement according to the invention.
  • the light particles of hydroxyapatite which in particular involve nanocrystalline structures that are partially contiguous, are not bound or adhered in the polymer matrix, but that the hydroxyapatite particles are present freely accessible in the pores. It can be recognized in particular that the particles are not densely surrounded by the polymer matrix, but usually only fill a portion of the respective pores.
  • FIG. 6 shows another SEM photomicrograph, in which the polymer matrix is provided with the label “cement matrix” and a hydroxyapatite particle is provided with the label “Ostim”.
US13/499,348 2009-09-30 2010-09-30 Bone cement and a method for producing same Abandoned US20120289608A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE102009043550A DE102009043550A1 (de) 2009-09-30 2009-09-30 Knochenzement und Verfahren zu dessen Herstellung
DE102009043550.6 2009-09-30
PCT/EP2010/005951 WO2011038905A2 (de) 2009-09-30 2010-09-30 Knochenzement und verfahren zu dessen herstellung

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2010/005951 A-371-Of-International WO2011038905A2 (de) 2009-09-30 2010-09-30 Knochenzement und verfahren zu dessen herstellung

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US14/527,872 Division US9993396B2 (en) 2009-09-30 2014-10-30 Bone cement and a method for producing same

Publications (1)

Publication Number Publication Date
US20120289608A1 true US20120289608A1 (en) 2012-11-15

Family

ID=43598317

Family Applications (2)

Application Number Title Priority Date Filing Date
US13/499,348 Abandoned US20120289608A1 (en) 2009-09-30 2010-09-30 Bone cement and a method for producing same
US14/527,872 Active US9993396B2 (en) 2009-09-30 2014-10-30 Bone cement and a method for producing same

Family Applications After (1)

Application Number Title Priority Date Filing Date
US14/527,872 Active US9993396B2 (en) 2009-09-30 2014-10-30 Bone cement and a method for producing same

Country Status (5)

Country Link
US (2) US20120289608A1 (de)
EP (1) EP2482861B1 (de)
DE (1) DE102009043550A1 (de)
ES (1) ES2593031T3 (de)
WO (1) WO2011038905A2 (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107469136A (zh) * 2016-06-07 2017-12-15 贺利氏医疗有限责任公司 糊状双组分聚甲基丙烯酸酯骨接合剂
US10471090B2 (en) 2016-05-19 2019-11-12 Heraeus Medical Gmbh Polymer solution for visco-supplementation

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102012014702A1 (de) 2012-07-25 2014-01-30 Heraeus Medical Gmbh Pastenförmiger Knochenzement

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1810300A (zh) * 2006-02-23 2006-08-02 北京茵普兰科技发展有限公司 微孔骨水泥和骨膏

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH611150A5 (de) * 1975-04-18 1979-05-31 Sulzer Ag
DE3314977A1 (de) * 1983-04-26 1984-10-31 ESPE Fabrik pharmazeutischer Präparate GmbH, 8031 Seefeld Verwendung von difunktionellen acrylsaeure- und methacrylsaeureestern zur herstellung von haertbaren knochenzementen
CH665357A5 (de) * 1985-07-05 1988-05-13 Werther Lusuardi Knochenzement.
RU2077329C1 (ru) 1993-07-21 1997-04-20 Акционерное общество закрытого типа "ОСТИМ" Средство для стимуляции роста костной ткани
DE4435680A1 (de) * 1994-10-06 1996-04-11 Merck Patent Gmbh Poröse Knochenersatzmaterialien
EP0734735B1 (de) * 1994-10-13 2002-01-16 Kuraray Co., Ltd. Zusammensetzung zum ausbessern von hartem gewebe auf basis von dimethacrylat-monomeren und versorgungseinheit dafür
RU2122520C1 (ru) 1996-10-31 1998-11-27 Акционерное общество закрытого типа "ОСТИМ" Способ получения суспензии гидроксиапатита
DE19939403B4 (de) * 1999-08-19 2004-02-12 fzmb Forschungszentrum für Medizintechnik und Biotechnologie e.V. Biologisch abbaubares Kompositmaterial
AU2000274383A1 (en) 2000-09-12 2002-03-26 Zakrytoe Aktsionernoe Obschestvo "Ostim" Preparation for treating diseases of bone tissues
ITMI20010089A1 (it) 2001-01-18 2002-07-18 Consiglio Nazionale Ricerche Metodo per l'ottenimento di un materiale composito polimero/ceramico bicompatibile avente una porosita' predeterminata
US20020115742A1 (en) 2001-02-22 2002-08-22 Trieu Hai H. Bioactive nanocomposites and methods for their use
DE10339953B3 (de) 2003-08-27 2005-04-21 Coripharm Medizinprodukte Gmbh & Co. Kg. Implantatmaterial für den Knochen-Knorpel-Ersatz und seine Verwendung
FR2870129A1 (fr) * 2004-05-14 2005-11-18 Ceravic Sas Soc Par Actions Si Ciment polymere pour la vertebroplastie percutanee
DE102004025030A1 (de) * 2004-05-18 2005-12-15 S&C Polymer Silicon- und Composite-Spezialitäten GmbH Nano-Apatit-Füllstoffe enthaltende härtbare Restaurationsmaterialien
US20060199876A1 (en) * 2005-03-04 2006-09-07 The University Of British Columbia Bioceramic composite coatings and process for making same
DE102005023094A1 (de) * 2005-05-13 2006-11-16 Nies, Berthold, Dr. Bioaktiver Knochenzement und seine Herstellung
DE112007003309B4 (de) * 2006-11-27 2013-02-07 Berthold Nies Knochenimplantat sowie Set zur Herstellung von Knochenimplantaten und seine Verwendung
JP5509098B2 (ja) * 2008-02-28 2014-06-04 ディーエフアイエヌイー・インコーポレーテッド 骨治療システムおよび方法
WO2010095001A1 (en) * 2009-02-19 2010-08-26 Yeditepe Universitesi Submicron monetite powders production
EP2498788B1 (de) * 2009-09-15 2019-01-09 University of Pittsburgh - Of the Commonwealth System of Higher Education Knochenersatzzusammensetzungen, herstellungsverfahren und klinische anwendungen

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1810300A (zh) * 2006-02-23 2006-08-02 北京茵普兰科技发展有限公司 微孔骨水泥和骨膏

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CN 1810300 A; 2006; English Machine Translation, provided by Espacenet on 10/7/2013 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10471090B2 (en) 2016-05-19 2019-11-12 Heraeus Medical Gmbh Polymer solution for visco-supplementation
CN107469136A (zh) * 2016-06-07 2017-12-15 贺利氏医疗有限责任公司 糊状双组分聚甲基丙烯酸酯骨接合剂
AU2017201842B2 (en) * 2016-06-07 2018-08-02 Heraeus Medical Gmbh Pasty two-component polymethacrylate bone cement
US10507261B2 (en) 2016-06-07 2019-12-17 Heraeus Medical Gmbh Pasty two-component polymethacrylate bone cement

Also Published As

Publication number Publication date
EP2482861B1 (de) 2016-09-07
EP2482861A2 (de) 2012-08-08
WO2011038905A2 (de) 2011-04-07
US9993396B2 (en) 2018-06-12
DE102009043550A1 (de) 2011-05-19
US20150051305A1 (en) 2015-02-19
WO2011038905A3 (de) 2011-07-07
ES2593031T3 (es) 2016-12-05

Similar Documents

Publication Publication Date Title
EP1592463B1 (de) Injizierbare knochenersatzmischung
He et al. Bone cements for percutaneous vertebroplasty and balloon kyphoplasty: Current status and future developments
Ishikawa Calcium phosphate cement
US20190216973A1 (en) Organophosphorous, multivalent metal compounds, & polymer adhesive interpenetrating network compositions & methods
US20040044096A1 (en) Reduced exothermic bone replacement cement
JP2010522591A (ja) ポリマー系をベースとするインプラント材料およびその使用
WO2009129316A2 (en) Minimally invasive treatment of vertebra (mitv) using a calcium phosphate combination bone cement
US9993396B2 (en) Bone cement and a method for producing same
US10426866B2 (en) Ternary mixture for a bone cement and method for its realisation
Moussi et al. Injectable macromolecule-based calcium phosphate bone substitutes
JP5886313B2 (ja) 生体材料およびそれを得る方法
JP5605618B2 (ja) 骨再生材料キット、ペースト状骨再生材料、骨再生材料及び骨接合材
AU2017278315A1 (en) Settable bone void filler
TWI465266B (zh) 用於骨水泥之添加劑及包含有該添加劑的骨水泥
Weiss et al. Injectable composites for bone repair
KR20040062946A (ko) 세포를 포함하는 주사가능한 칼슘염 골충전제
Daculsi et al. Multiphasic Biomaterials: A Concept for Bone Substitutes Developed in the" Pays de la Loire"

Legal Events

Date Code Title Description
AS Assignment

Owner name: AAP BIOMATERIALS GMBH, GERMANY

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:SATTIG, CHRISTOPH;DINGELDEIN, ELVIRA;SIGNING DATES FROM 20120515 TO 20120525;REEL/FRAME:028357/0649

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION