WO1986001113A1 - Materiau de remplacement d'os - Google Patents

Materiau de remplacement d'os Download PDF

Info

Publication number
WO1986001113A1
WO1986001113A1 PCT/NL1985/000033 NL8500033W WO8601113A1 WO 1986001113 A1 WO1986001113 A1 WO 1986001113A1 NL 8500033 W NL8500033 W NL 8500033W WO 8601113 A1 WO8601113 A1 WO 8601113A1
Authority
WO
WIPO (PCT)
Prior art keywords
polymeric material
mpa
biodegradable polymeric
ceramic
composition
Prior art date
Application number
PCT/NL1985/000033
Other languages
English (en)
Inventor
Gerrit Johannes Brinks
Jan Cornelis Brinks
Original Assignee
Gerrit Johannes Brinks
Jan Cornelis Brinks
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 Gerrit Johannes Brinks, Jan Cornelis Brinks filed Critical Gerrit Johannes Brinks
Publication of WO1986001113A1 publication Critical patent/WO1986001113A1/fr

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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
    • 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
    • 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

Definitions

  • This invention relates to a composition suitable for use as an impant material in human beings and animals to replace absent bone tissue, and comprising a biocompatible particulate ceramic material as a bone-replacing component and a biodegradable polymeric material.
  • a similar material is disclosed in NL-A-7704659.
  • the inorganic component or both the inorganic and the organic components are resorbable.
  • Other known materials consist virtually entirely of a calcium phosphate compound, for example, hydroxylapatite in the form of hard shapes which prior to use have to be subjected to all sorts of complicated operations, or of a mixture of a calcium phosphate compound with polymers which for example have to harden in the site of implantation, or of loose granulate of, for example, hydroxylapatite .
  • a composition suitable for use as an implant material in human beings and animals to replace absent bone tissue comprising a biocompatible, particulate ceramic material as a bone-replacing component and a biodegradable polymeric material, characterized in that the ceramic material is a non-resorbable material, and the biodegradable polymeric material functions as a binder for said ceramic material, the composition being an intimate mixture of, by weight,
  • the invention is based on the insight that, after the implantation of the composition according to the invention in the human or animal body the biodegradability of the polymeric material functioning as a binder will ensure that it is broken down in the course of time, and will disappear, leaving a microporous structure of the (bio)ceramic material into which new blood vessels and connective tissue can grow.
  • biodegradable polymeric materials suitable for use in the composition according to the invention are the reticulating polymers gelatin A or B, carboxymethyl " cellulose and dextran, which are all polymers of natural origin, but polyethylene glycol, for example, is also suitable Generally speaking, any biodegradable organic compound capable of forming a network or reticulation, and hence capable of functioning as a binder for the biocompatible ceramic material, and which further satisfies the general requirements as imposed in the pharmacopeias, for example, The Netherlands, European and North-American pharmacopeias is suitable for use as an adjuvant in the material according to the present invention.
  • gelatin A or B is a polymer made from skin or bones, and satisfies the requirements imposed in the various pharmacopeias. It is a mixture of protein molecules, is biocompatible and biodegradable, and is already being widely applied in injection compositions.
  • Carboxymethyl cellulose is a polysaccharide of vegetable origin with a molecular weight of l ⁇ -l ⁇ 6. in the form of the sodium salt this polymer is water-soluble. It satisfies the above requirements and is also frequently being used in injection compositions.
  • the polyethylene glycol is a white to off-white viscous composition with a molecular weight of 200-6000 and is also already, being used in pharmaceutical compositions.
  • biocompatible, non-resorbable ceramic material for use in the implant material according to this invention will naturally also have to satisfy the general requirements as defined in the pharmacopeias, in particular the above Netherlands, European and North-American pharmacopeias.
  • Ceramic materials of the above type which already have found application in practice as an implant material and are also suitable for use as a bone-replacing component in the implant material according to this invention are hydroxylapatite » referred to hereinbefore and, in general a calcium phosphate compound.
  • the hydroxylapatite is a white to off-white calcium phosphate compound having the chemical formula Ca o(P ⁇ )6(OH) _
  • the compound is a solid and consists of approximately spherica particles with a porosity of between 1 and 50%. Its particle size is about 0.07-0.2 mm.
  • the compound is normally purified by treatment with hydrogen peroxide, followed by intensive washing with distilled water. The compound is fully biocompati and not resorbable after implantation in human and animal bone tissues.
  • The.more general calcium phosphate compound refers to a compound which is available in the form of a white powder and can be represented by the generic chemical formula Ca x (H y PO z ) .nH2 ⁇ , in which x represents 1, 2 or 3, y is 0, 1 or 2 ; z is 3 or 4; m is 1 or 2; and n represents 0, 1 or 2.
  • the compound is a non-toxic, biocompatible material which is often being used as an adjuvant in the pharmaceutical industry and has recently been found to be suitable for use as an implant material.
  • Aluminum oxide with the chemical formula Al2 ⁇ 3.nH2 ⁇ also has known applications as an implant material, and is therefore suitable for use in the implant material accordi to the present invention.
  • any inorganic or ceramic compound that is biocompatible and non-resorbable and can be processed for preparing the implant material of the invention is suitable for this purpos
  • Further examples are Si ⁇ 2-nH2 ⁇ , GeO and GaS.
  • the particle size of the ceramic material should not be too large.
  • the particle size should not be larger than about 1.5 mm.
  • this material has a highly viscous consistency so that it is mouldable by kneading or modelling, but it can also be provided as a shaped material in the form of plates, rods or bars.
  • the material according to the invention can be used as such in the case of a bone defect where bone tissue is locally absent and this void is in a form corresponding to the shape of the material.
  • the plates, rods or bars are by themselves deformable or breakable.
  • the composition according to the invention comprises, by weight, 4-307, of biodegradable polymer and 15-307, water and balance bone-replacing ceramic component.
  • the use of less water in the composition increases the risk of the composition being less easy to handle and process, because the binder function of the biodegradable polymeric material is suboptimal.
  • composition according to the invention may incorporate more biodegradable polymeric materia
  • the implant material has such a viscosity that it can be introduced by means of an injection syringe.
  • the invention also relates to a method of producing the composition for use as an implant material, said method being characterized in that a gelled mixture, prepared from the biodegradable polymeric material and water is intimately mixed with the ceramic component, using a high-power, low-spe kneader at a temperature of no more than 60°C, and subjecting the mixture thus produced to an- elevated pressure of at least 10 Mpa at room temperature for at least about 5 minutes.
  • a gelled mixture prepared from the biodegradable polymeric material and water is intimately mixed with the ceramic component, using a high-power, low-spe kneader at a temperature of no more than 60°C, and subjecting the mixture thus produced to an- elevated pressure of at least 10 Mpa at room temperature for at least about 5 minutes.
  • This biodegradable polymeric material e.g. gelatin, carboxymethyl cellulose, or dextran
  • a 807 ethanol solution in water has first been treated with a 807. ethanol solution in water and dried at 110-120°C.
  • the treatment with a 807, ethanol solution in water is given because when a less concentrated solution is used, e.g. a 707, ethanol solution in water, the polymeric material may swell unduly
  • a gel material is formed, which may take about 2 hours. This process step is completed by homogenizing the gel (material B) .
  • material A is slowly added to material B in discrete portions with careful stirring, mixing or kneading.
  • a temperature of up to 60°C is permissible, operation at elevated temperature being generally beneficial inasmuch as it facilitates kneading by decreasing the viscosit Taking this circumstance into account, therefore, the mixing operation is preferably carried out at elevated temperature.
  • the product produced by the mixing operation described already exhibits a certain coherence, but is in many cases nevertheless too brittle.
  • the ultimate composition, produced by mixing with the bone- replacing component is subjected, in a mould, to an elevated pressure of at least about 10 MPa for at least about 5 minutes to produce an end product of sufficient coherence.
  • this pressure stage the amount of the pressure and the time for which the pressure is applied are important parameters. It has been found that this stage can be carried out at room temperature, and further that when a given pressur is used it is possible to determine a duration for this treatment after which no appreciable changes in the nature of the material under pressure take place any longer. It can be assumed that the interaction between the particles of ceramic material and the biodegradable polymer, which partly causes the formation of an adsorption bond between the polymer and the ceramic particles, no longer has any effect, or that the bonding process is completed. The product thus obtained is then ready to be packaged and subsequently sterilized, whereafter it can be used.
  • the amount of the pressure to be used depends partly upon the nature of the biodegradable adjuvant used. Thus when gelatin is used a preferred pressure range is from 10 to 30 MPa, and in the case of carboxymethyl cellulose a pressure of 75-150 MPa.
  • the amount of the pressure to be applied is also selecte with a view to the desired consistency of the implant material
  • a pressure of about 455 MPa is used, a product is obtaine which is excellently suitable for being shaped into the implant material in the form of plates, rods or bars.
  • a pressure of less than about 150 MPa ensures the production of a product having a good plasticity.
  • a pressure is used with a value in the intermediate range of about 150-455 M the plastic properties of the resulting product are not unequivocal or insufficiently so, and such a product is less suitable for use in practice.
  • the composition according to the invention is highly viscous and kneadable and can easily be applied with a spatula Accordingly, it is ready for use as an implant material. Owing to the selection of the formulation, the composition according to the invention is hydrophilic and slowly absorbs wound fluid from its surroundings. Owing to the relatively low concentration of polymer, there is a direct contact between the ceramic material and wound fluid, while yet, owing to the pressure step, the ceramic particles, for example apatite particles, are densely packed.
  • the implant material according to the invention which has a specific mass ranging from 1.2 x 10 3 and 3.5 x 10 3 kg/m 3 is a product having a greatly improved processabilit , which amply satisfies the requirements imposed thereon in practice.
  • fields of application are surgery, traumatology, implantology, orthopedics, paradontology, dental surgery and general dentistry.
  • Example III 74 g calcium phosphate (anhydrous) was treated in the manner described in Example I with H2O2 in distilled water. 4 g of the sodium compound of carboxymethyl cellulose was sprinkled onto 22 cm 3 distilled water having a temperature of 60°C. After 2 hours the gel was homogenized. The remainder of the procedure was similar to Example I, except- that the pressure applied was about 152 MPa.
  • Example III
  • the mass thus obtained was introduced into a disinfected mould and pressed for 5 minutes using room temperature and a pressure of 110 MPa.
  • the resulting plates exhibited a brittle fracture when pressed with a spatula.
  • Example V Similarly to Example IV, 2 g carboxymethyl cellulose was sprinkled onto 4.3 cm 3 of distilled water, and 13.7 g hydroxylapatite was mixed with the gel.
  • Example VI apex restoration.
  • Example VII use in capping dental implants.
  • Example VI In the same manner as in Example VI, a clinical examinat was made, but now regarding the capping of dental implants. Evaluation etc. was as in Example VI.
  • Example II 87. gelatin
  • CMC Example III
  • Example VIII filling alveolus after extraction.
  • Example II In the same way as in Examples VI and VII a clinical examination was made, but now into the applicability for filling the alveolus after extraction. Three patients took part in the examination. In one patient the product of Example I (87, gelatin) was used, and in two patients the product of Example III.
  • Example IX In one case in which the product of Example III was used, the results were even so good (as regards maintaining and building jaw bone) that after 6 months a dental implant could be, and was, placed in the site of implantation and hence in the newly-formed bone tissue. Evaluation after a total period of 12 months gave the desired clinical and radiological picture.
  • Example IX Example IX

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Transplantation (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Dermatology (AREA)
  • Medicinal Chemistry (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Composite Materials (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Materials For Medical Uses (AREA)

Abstract

Une composition est utile comme matériau pour implants chez des êtres humains et des animaux, afin de remplacer un tissu osseux absent. Le matériau comprend un matériau céramique particulaire biocompatible comme composant de remplacement du tissu osseux, et un matériau polymère biodégradable. Le matériau céramique n'est pas résorbé, et le matériau polymère biodégradable agit comme liant dudit matériau céramique, la composition étant formée d'un mélange intime de 4-30% en poids dudit matériau polymère, 15-30% d'eau et le reste de matériau céramique. Ce mélange intime est pétrissable et a une consistance à viscosité élevée. La composition est préparée en mélangeant intimement un mélange gélifié composé du matériau polymère biodégradable et d'eau avec le composant céramique à l'aide d'un malaxeur à grand puissance et à vitesse réduite, à une température ne dépassant pas 60oC, et un soumettant le mélange ainsi obtenu à une pression élevée d'au moins 10 MPa à la température ambiante pendant au moins 5 minutes environ.
PCT/NL1985/000033 1984-08-17 1985-08-15 Materiau de remplacement d'os WO1986001113A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NL8402534A NL8402534A (nl) 1984-08-17 1984-08-17 Materiaal, geschikt voor toepassing als implantatiemateriaal bij mens en dier ter vervanging van afwezig botweefsel, alsmede werkwijze ter bereiding van het materiaal.
NL8402534 1984-08-17

Publications (1)

Publication Number Publication Date
WO1986001113A1 true WO1986001113A1 (fr) 1986-02-27

Family

ID=19844336

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/NL1985/000033 WO1986001113A1 (fr) 1984-08-17 1985-08-15 Materiau de remplacement d'os

Country Status (3)

Country Link
EP (1) EP0191086A1 (fr)
NL (1) NL8402534A (fr)
WO (1) WO1986001113A1 (fr)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2601593A1 (fr) * 1986-07-16 1988-01-22 Du Pin Cellulose Materiau hydrophile biocompatible, procede de fabrication et applications
FR2606282A1 (fr) * 1986-11-12 1988-05-13 Ecole Nale Sup Ceramique Indle Composition durcissable pour le comblement des cavites osseuses
WO1988003417A1 (fr) * 1986-11-03 1988-05-19 Material Consultants Oy Materiau biocomposite a usage chirurgical et procede de production dudit materiau
EP0298501A2 (fr) * 1987-07-10 1989-01-11 Asahi Kogaku Kogyo Kabushiki Kaisha Composition pour la fabrication d'un matériau durcissable du type phosphate de calcium et procédé pour la production d'un tel matériau
EP0323632A1 (fr) * 1987-12-28 1989-07-12 Asahi Kogaku Kogyo Kabushiki Kaisha Composition pour la fabrication d'un matériau durcissable du type phosphate de calcium et procédé pour la production d'un tel matériau
EP0329239A2 (fr) * 1988-02-16 1989-08-23 Giancarlo Foresti Préparation chirurgicale à activité ostéotropique
US5180426A (en) * 1987-12-28 1993-01-19 Asahi Kogaku Kogyo K.K. Composition for forming calcium phosphate type setting material and process for producing setting material
DE4216496A1 (de) * 1992-05-19 1993-11-25 Werner Prof Dr Med Sattel Plombenkörper zum Einsetzen in eine Knochenhöhle, insbesondere in den Markraum eines Röhrenknochens
FR2715853A1 (fr) * 1994-02-08 1995-08-11 Centre Nat Rech Scient Composition pour bio-matériau; procédé de préparation.
FR2737663A1 (fr) * 1995-08-07 1997-02-14 Centre Nat Rech Scient Composition pour bio-materiau, procede de preparation
WO1998044964A1 (fr) * 1997-04-04 1998-10-15 Bioxid Oy Composition biocompatible, procedes permettant de la preparer et ses utilisations
US8048443B2 (en) 2005-12-16 2011-11-01 Cerapedics, Inc. Pliable medical device and method of use
US9265857B2 (en) 2010-05-11 2016-02-23 Howmedica Osteonics Corp. Organophosphorous, multivalent metal compounds, and polymer adhesive interpenetrating network compositions and methods
US11235086B2 (en) 2018-02-22 2022-02-01 Cerapedics, Inc. Processes for coating inorganic particles with a peptide or protein useful for improving cellular activity related to bone growth

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2518153A1 (de) * 1975-04-18 1976-10-28 Sulzer Ag Zur verankerung von implantaten im knochen dienende mischung
FR2350826A1 (fr) * 1976-05-12 1977-12-09 Battelle Institut E V Materiau de remplacement des os, d'assemblage des os et d'ancrage des protheses et procede pour sa fabrication
FR2364644A1 (fr) * 1976-09-20 1978-04-14 Inst Nat Sante Rech Med Nouveau materiau de prothese osseuse et son application
FR2374040A1 (fr) * 1976-12-17 1978-07-13 Scheicher Hans Agent de recouvrement et/ou de remplissage d'imperfections osseuses et son procede de fabrication
GB2032777A (en) * 1978-10-09 1980-05-14 Merck Patent Gmbh Bioresorbable masses containing collagen
EP0115549A1 (fr) * 1983-02-03 1984-08-15 Ethicon, Inc. Pâte pour l'hémostase et pour le soulagement temporaire des défauts dans le traumatisme des os

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2518153A1 (de) * 1975-04-18 1976-10-28 Sulzer Ag Zur verankerung von implantaten im knochen dienende mischung
FR2350826A1 (fr) * 1976-05-12 1977-12-09 Battelle Institut E V Materiau de remplacement des os, d'assemblage des os et d'ancrage des protheses et procede pour sa fabrication
FR2364644A1 (fr) * 1976-09-20 1978-04-14 Inst Nat Sante Rech Med Nouveau materiau de prothese osseuse et son application
FR2374040A1 (fr) * 1976-12-17 1978-07-13 Scheicher Hans Agent de recouvrement et/ou de remplissage d'imperfections osseuses et son procede de fabrication
GB2032777A (en) * 1978-10-09 1980-05-14 Merck Patent Gmbh Bioresorbable masses containing collagen
EP0115549A1 (fr) * 1983-02-03 1984-08-15 Ethicon, Inc. Pâte pour l'hémostase et pour le soulagement temporaire des défauts dans le traumatisme des os

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4904258A (en) * 1986-07-16 1990-02-27 La Cellulose Du Pin Biocompatible, hydrophilic material, method of manufacture and uses of same
EP0256906A1 (fr) * 1986-07-16 1988-02-24 La Cellulose Du Pin Matériau hydrophyle biocompatible, et son procédé de fabrication
FR2601593A1 (fr) * 1986-07-16 1988-01-22 Du Pin Cellulose Materiau hydrophile biocompatible, procede de fabrication et applications
WO1988003417A1 (fr) * 1986-11-03 1988-05-19 Material Consultants Oy Materiau biocomposite a usage chirurgical et procede de production dudit materiau
FR2606282A1 (fr) * 1986-11-12 1988-05-13 Ecole Nale Sup Ceramique Indle Composition durcissable pour le comblement des cavites osseuses
EP0298501A2 (fr) * 1987-07-10 1989-01-11 Asahi Kogaku Kogyo Kabushiki Kaisha Composition pour la fabrication d'un matériau durcissable du type phosphate de calcium et procédé pour la production d'un tel matériau
EP0298501A3 (en) * 1987-07-10 1989-06-14 Asahi Kogaku Kogyo Kabushiki Kaisha Composition for forming calcium phosphate type hardening material and process for producing such hardening material
US5281404A (en) * 1987-12-28 1994-01-25 Asahi Kogaku Kogyo K.K. Composition for forming calcium phosphate type setting material and process for producing setting material
US5180426A (en) * 1987-12-28 1993-01-19 Asahi Kogaku Kogyo K.K. Composition for forming calcium phosphate type setting material and process for producing setting material
EP0323632A1 (fr) * 1987-12-28 1989-07-12 Asahi Kogaku Kogyo Kabushiki Kaisha Composition pour la fabrication d'un matériau durcissable du type phosphate de calcium et procédé pour la production d'un tel matériau
EP0329239A3 (fr) * 1988-02-16 1990-08-08 Giancarlo Foresti Préparation chirurgicale à activité ostéotropique
EP0329239A2 (fr) * 1988-02-16 1989-08-23 Giancarlo Foresti Préparation chirurgicale à activité ostéotropique
DE4216496A1 (de) * 1992-05-19 1993-11-25 Werner Prof Dr Med Sattel Plombenkörper zum Einsetzen in eine Knochenhöhle, insbesondere in den Markraum eines Röhrenknochens
US5717006A (en) * 1994-02-08 1998-02-10 Centre National De La Recherche Scientifique (C.N.R.S.) Composition for biomaterial; preparation process
FR2715853A1 (fr) * 1994-02-08 1995-08-11 Centre Nat Rech Scient Composition pour bio-matériau; procédé de préparation.
WO1995021634A1 (fr) * 1994-02-08 1995-08-17 Centre National De La Recherche Scientifique (C.N.R.S.) Composition pour bio-materiau; procede de preparation
AU693517B2 (en) * 1994-02-08 1998-07-02 Centre National De La Recherche Scientifique (C.N.R.S.) Biomaterial composition and method for preparing same
WO1997005911A1 (fr) * 1995-08-07 1997-02-20 Centre National De La Recherche Scientifique (Cnrs) Composition pour bio-materiau, procede de preparation
FR2737663A1 (fr) * 1995-08-07 1997-02-14 Centre Nat Rech Scient Composition pour bio-materiau, procede de preparation
AU707039B2 (en) * 1995-08-07 1999-07-01 Centre National De La Recherche Scientifique (Cnrs) Composition for a biomaterial, process of preparation
US6001394A (en) * 1995-08-07 1999-12-14 Centre National De La Recherche Scientifique (C.N.R.S.) Biomaterial composition and method for preparing same
WO1998044964A1 (fr) * 1997-04-04 1998-10-15 Bioxid Oy Composition biocompatible, procedes permettant de la preparer et ses utilisations
US8048443B2 (en) 2005-12-16 2011-11-01 Cerapedics, Inc. Pliable medical device and method of use
US9101694B2 (en) 2005-12-16 2015-08-11 Cerapedics Inc. Pliable medical device and method of use
US9265857B2 (en) 2010-05-11 2016-02-23 Howmedica Osteonics Corp. Organophosphorous, multivalent metal compounds, and polymer adhesive interpenetrating network compositions and methods
US10286102B2 (en) 2010-05-11 2019-05-14 Howmedica Osteonics Corp Organophosphorous, multivalent metal compounds, and polymer adhesive interpenetrating network compositions and methods
US11235086B2 (en) 2018-02-22 2022-02-01 Cerapedics, Inc. Processes for coating inorganic particles with a peptide or protein useful for improving cellular activity related to bone growth

Also Published As

Publication number Publication date
EP0191086A1 (fr) 1986-08-20
NL8402534A (nl) 1986-03-17

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