CA1107582A - Composite implant materials and process for preparing same - Google Patents

Composite implant materials and process for preparing same

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Publication number
CA1107582A
CA1107582A CA302,862A CA302862A CA1107582A CA 1107582 A CA1107582 A CA 1107582A CA 302862 A CA302862 A CA 302862A CA 1107582 A CA1107582 A CA 1107582A
Authority
CA
Canada
Prior art keywords
resins
sintered
sintered apatite
composite implant
apatite
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.)
Expired
Application number
CA302,862A
Other languages
French (fr)
Inventor
Atsushi Tomonaga
Hideki Aoki
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.)
Kureha Corp
Original Assignee
Kureha Corp
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 Kureha Corp filed Critical Kureha Corp
Application granted granted Critical
Publication of CA1107582A publication Critical patent/CA1107582A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61C—DENTISTRY; APPARATUS OR METHODS FOR ORAL OR DENTAL HYGIENE
    • A61C8/00—Means to be fixed to the jaw-bone for consolidating natural teeth or for fixing dental prostheses thereon; Dental implants; Implanting tools
    • A61C8/0012—Means to be fixed to the jaw-bone for consolidating natural teeth or for fixing dental prostheses thereon; Dental implants; Implanting tools characterised by the material or composition, e.g. ceramics, surface layer, metal alloy
    • A61C8/0016—Means to be fixed to the jaw-bone for consolidating natural teeth or for fixing dental prostheses thereon; Dental implants; Implanting tools characterised by the material or composition, e.g. ceramics, surface layer, metal alloy polymeric material
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61C—DENTISTRY; APPARATUS OR METHODS FOR ORAL OR DENTAL HYGIENE
    • A61C8/00—Means to be fixed to the jaw-bone for consolidating natural teeth or for fixing dental prostheses thereon; Dental implants; Implanting tools
    • A61C8/0012—Means to be fixed to the jaw-bone for consolidating natural teeth or for fixing dental prostheses thereon; Dental implants; Implanting tools characterised by the material or composition, e.g. ceramics, surface layer, metal alloy
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2/00—Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
    • A61F2/02—Prostheses implantable into the body
    • A61F2/28—Bones
    • 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
    • A61L27/02—Inorganic materials
    • A61L27/12—Phosphorus-containing materials, 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
    • 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
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2/00—Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
    • A61F2/02—Prostheses implantable into the body
    • A61F2/30—Joints
    • A61F2002/30001—Additional features of subject-matter classified in A61F2/28, A61F2/30 and subgroups thereof
    • A61F2002/30003—Material related properties of the prosthesis or of a coating on the prosthesis
    • A61F2002/3006—Properties of materials and coating materials
    • A61F2002/30065—Properties of materials and coating materials thermoplastic, i.e. softening or fusing when heated, and hardening and becoming rigid again when cooled
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2/00—Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
    • A61F2/02—Prostheses implantable into the body
    • A61F2/30—Joints
    • A61F2002/30001—Additional features of subject-matter classified in A61F2/28, A61F2/30 and subgroups thereof
    • A61F2002/30108—Shapes
    • A61F2002/30199—Three-dimensional shapes
    • A61F2002/30224—Three-dimensional shapes cylindrical
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2/00—Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
    • A61F2/02—Prostheses implantable into the body
    • A61F2/30—Joints
    • A61F2/3094—Designing or manufacturing processes
    • A61F2002/30968—Sintering
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2210/00—Particular material properties of prostheses classified in groups A61F2/00 - A61F2/26 or A61F2/82 or A61F9/00 or A61F11/00 or subgroups thereof
    • A61F2210/0071—Particular material properties of prostheses classified in groups A61F2/00 - A61F2/26 or A61F2/82 or A61F9/00 or A61F11/00 or subgroups thereof thermoplastic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2230/00—Geometry of prostheses classified in groups A61F2/00 - A61F2/26 or A61F2/82 or A61F9/00 or A61F11/00 or subgroups thereof
    • A61F2230/0063—Three-dimensional shapes
    • A61F2230/0069—Three-dimensional shapes cylindrical
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2310/00—Prostheses classified in A61F2/28 or A61F2/30 - A61F2/44 being constructed from or coated with a particular material
    • A61F2310/00005—The prosthesis being constructed from a particular material
    • A61F2310/00179—Ceramics or ceramic-like structures
    • A61F2310/00293—Ceramics or ceramic-like structures containing a phosphorus-containing compound, e.g. apatite

Abstract

ABSTRACT OF THE DISCLOSURE
Disclosed is a composite implant material comprising a sintered d apatite material and a thermoplastic or thermo-setting resin. Said composite material is prepared by forming a sintered apatite material and filling or impregnat-ing a thermoplastic or thermosetting resin into the pores or holes of the sintered apatite material, which have been formed during the formation of said sintered material or perforated after the formation thereof. Said composite implant material has controlled compatibility to bone as well as excellent physical strength.

Description

5~2 FIELD OF THE INVENTION
The invention relates to composite implant materials, particularly composite materials of apatite useful for artificial prostheses in orthopedic and dental fields, and to a process for the preparation thereof.

BACKGROUND OF THE INVENTION
Various metallic, plastics and ceramic materials have hitherto been used as an implant material for a bone or tooth in the orthopedic and dental fields. However, these conventional materials are not satisfactory since they are poor in compatibility to bone in a human or animal body.
Apatite is represented by the formula Ca1O(PO4)6~OH,F,Cl)2 which may further contain 1 to 10~ of carbonate ion (CO3 ).
Such an apatite substance constitutes a main component of the minerals of bones and teeth in vertebrate and has chemical properties such as being soluble in an acid, -~ little or slightly soluble in water and highly stable in an alkali. It is known, on the other hand, that sintered apatite materials obtainable by sintering apatite at a high temperature have no toxicity and are excellent in compati-bility to bone in a human or animal body. Therefore, the sintered apatite materials have increasingly become of great interest in the orthopedic and dental fields. However, the sintered apatite materials have insufficient mechanical strength, paricularly low impact strength, and therefore, must be improved in strength in order to make it possible to employ them as an implant material for a part to which body weight is to be loaded, for example (see, H. Aoki et al, Ceramics, "Apatite as a Biomaterial", 10 [7] 1975, PP. 57-66).

~¢3 75~2 SUMMARY OF THE INVENTION
It has now been found that the use of a plastics material in combination with a sintered apatite material makes it possible not only to improve the strength inherent to the sintered apatite material but, also, to moderately control the compatibility of the sintered apatite material to bone, and; hence, composite materials of a sintered apatite material with a plastics material can provide very useful implant materials.
Thus, the principal object of the present invention is to provide composite implant materials which can avoid the above-mentioned drawbacks encountered with the conven-tional implant materials and are excellent in both physical and chemical properties.
According to the present invention, a composite implant material comprises a sintered apatite material and a thermoplastic or thermosetting resin, at least said sintered apatite material existing in a continuous phase and the respective phases of said sintered apatite material and said thermoplastic or thermosetting resin being exposed, in part, to the surface of said implant material.
- The present invention also provides a process for , preparing the composite implant material according to the invention, which process comprises forming a sintered apatite material and filling or impregnating a thermo-; plastic or thermosetting resin into the pores or holes of the sintered apatite material, which have been formed during the formation of said sintered apatite material or perforated into a desired configuration after the formation of said sintered apatite material.
. . .

, . . .

S~Z

BRIEF DESCRIPTION OF THE DRAWINGS
Figs. 1 through 3 schematically illustrat the embodiments of the arrangement of the sintered apatite material phase and the thermoplastic or thermosetting resin phase in the composite implant material formed into a columnar shape.
DESCRIPTION OF PREEERRED EMBODIMENTS
Apatite to be employed in the present invention may preferably be hydroxyapatite (Cal0(PO4)6(OH)2). Hydroxyapatite may contain a certain amount of whitlockite (Ca3(PO4)2), if desirable from the view point of the affinity to bone or the strength. The preparation and the sintering of apatite may be carried out, for example, by a method as described in the Japanese publication hereinbefore mentioned. The sintered apatite material may, thus, be obtained in a porous or dense state. The composition of the resulting sintered apatite material can be desirably controlled by appropriately selecting the composition of the starting material or the condition for the preparation or sintering of apatite. Likewise, the porosity of the resulting sintered apatite material can also be desirably controlled.
The thermoplastic or thermosetting resins usable for the present invention may be selected from those which are well known in the art. Examples of such resins include polyethylene, polypropylene, polymethyl methacrylate, polyurethane, polyester, acrylonitrile-butadiene-styrene resins, fluorocarbons, polyamides, polyacetals, polycarbonate, polysulfone, epoxy resins, silicone resins, diallyl phthalate resins and furan resins. These resins may contain reinforcing materials such as carbon, silicon carbide, glass, alumina, . . - , ' ~ ' - : ' :~lQ75~2 magnesia, zirconia, tungsten, molybdenum, stainless steel and the like, and other fillers. It is desirable that ; these resins and reinforcing materials be selected so as to provide desired properties, such as mechanical strength and stability, to the resulting composite material, according to the intended use thereof. However, it is important that they be selected in careful consideration of innocuity against a living body and of good processability.
Where the sintered apatite material is as dense as to have a porosity of not more than 20~, the resin may not be or very scarcely be impregnated into the sintered apatite material. However, where the sintered apatite material has a porosity above 20~, the resin may be directly impregnated into the pores of the sintered apatite material. That is - 15 to say, in the process of the present invention, the sintered apatite material may be formed into a porous state so that the resin may be impregnated into the pores to obtain a composite material. Alternatively, if the sintered apatite s material is so dense that the resin may not be impregnated, or if an additional amount of the resin is to be impregnated, or the resin is to be filled into the sintéred apatite material in a desired configuration, the sintered apatite material may be formed with a desired porosity, perforated into a desired configuration by mechanical perforation, or chemical treatment, or by perforation by means of an ultra-sonic wave vibration, laser, water jet or the like, and then, filled or impregnated with the resin into the pores or holes. Then, the resin may be hardened or cured by a conventional method.
In the resultant composite implant material according 5~?2 to the present invention, the sintered apatite material, thus, exist in a continuous phase, which is desirable since the sintered apatite material phase is exposed onto the major part of the surface of the composite implant material.
The embodiments of the arrangement of the sintered apatite material phase and the thermoplastic or thermosetting resin phase in a columnar shaped composite implant material according to the invention are schematically illustrated in the accompanying drawings. In the figures, 1 denotes the sintered apatite material phase and 2 denotes the resin phase. Naturally, the configuration of the composite implant material of the present invention is not limited to those as shown in these figures. For example, the resin may be filled or impregnated in various configurations according to the configurations of the pores or holes formed during the preparation of the sintered apatite material or perforated after the formation of the sintered apatite material.
The composite apatite materials according to the present invention are excellent in both physical and chemical properties. They can be obtained as a molded article in a prescribed shape and, hence, are very suitable as an implant material for orthopedic and dental uses. They can be safely buried in a human or animal body as a prosthesis for a bone or tooth damaged by an accident or by a disease such as bone tumor, dental carries or serious periodontic disease, and intimately bound to a vital tissue without any rejection phenomena while maintaining the high strength thereof.
Further, the composite implant materials according to the invention have a surprising advantage in that their , 51~2 compatibility to bone can be controlled as desired. Upon the use of an implant material for the replacement of a bone or tooth, particularly of a tooth root, it may be necessary to take out the buried implant material from the living body immediately when any troubles are found after --the implantation of the material. In such a case, it is very important that the implant material has a moderate affinity for bone, in order to make it possible to take out the implanted material as required.
The following example will further illustrate the present invention.
Example A. 74 g of purified Ca(OH)2 was stirred into 2 ~
of distilled water. To the obtained suspension, 2 ~ of a solution of about 70 g of 80% phosphoric acid in distilled water was slowly added, to adjust the pH value to approxi-mately 7.0, and they were reacted at 25C, for 1 hour with stirring. Then, the reaction mixture was allowed to stand at room temperature for 24 hours. The reaction product was then collected through centrifuging and dried. The obtained dry powder was microcrystalline calcium phosphate having a Ca/P ratio of about 1.6, which had a composition and construc-tion analogous to those of stoichiometrical hydroxyapatite having a Ca/P ratio of 1.67.
Then, the calcium phosphate powder was blended with an amount of Ca(OH)2 sufficient to supplement the deficiency of calcium as compared with stoichiometrical hydroxyapatite and they were reacted at 800C in the air.
The X-ray diffraction and the thermal analysis of the resultant powder proved that it was pure crystalline hydroxyapatite, ~1~75~:

stable even at a high temperature of up to 1400C.
B. The hydroxyapatite powder obtained as mentioned above was dressed into a grain size of 250 mesh and, then, press molded, under 1,000 kg/cm2, for 5 minutes, into a column of a diameter of 10 mm. The column was then sintered in the air, at 1300C, for 3 hours.
The sintered product thus obtained had a density corresponding to about 95~ of the theoretical density (which corresponds to a porosity of about 5%), a compressive strength of about 1,500 kg/cm2 and a flexural strength of 700 kg/cm2.
C. The sintered apatite column was perforated by means of ultrasonic wave vibration so as to obtain the holes of the shape and arrangement as seen in Fig. 1 with an ; opening percentage (a percentage of the volume of the holesto the whole volume) of about 30%. The perforated column was impregnated under vacuum, at 80C, for 30 minutes, with an epoxy resin havin~ a composition of, 100 parts by weight of an epoxy resin (Epon 828 available from Shell Chemical Co.), 90 parts by weight of a curing agent (methyl nadic anhydride~,
2 parts by weight of a curing accelerator (tri-(di-methylamino)-methylphenol), and the resin was cured at 160C, for 3 hours.
The columnar composite material thus obtained had a compressive strength and flexural strength approximately equivalent to those as mentioned in B, above. A block sample of a composite material of a size of lOxlOx5 mm, ; produced by the procedure as mentioned above, was dropped from a height of 10 m onto a concrete surface to prove the 5~2 excellent impact strength of the composite material of the invention. The sample was not broken at all. A sample of an article of the same size consisting of only the sintered apatite material produced as mentioned above was broken into three pieces in the above-mentioned test.
D. The composite column thus obtained was buried in a tooth extraction fovea of an adult dog as an artificial tooth root. Observation for a period of one month proved that the column was non-toxic and moderately bound to the mandibula of the dog.

Claims (8)

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:
1. A composite implant material usable as a prosthesis for a bone or tooth, comprising a perforated sintered apatite material having perforation holes formed therein in a desired configuration and a thermoplastic or thermosetting resin, at least said perforated sintered apatite material existing in a continuous phase, said resin being filled or impregnated into said holes, and the respective phases of said sintered apatite material and said resin being exposed, in part, to the surface of said implant material.
2. A composite implant material according to claim 1, wherein said sintered apatite material comprises hydroxy-apatite.
3. A composite implant material according to claim 1, wherein said thermoplastic or thermosetting resin is selected from the group consisting of polyethylene, poly-propylene, polymethyl methacrylate, polyurethane, polyester, acrylonitrile-butadiene-styrene resins, fluorocarbons, poly-amides, polyacetals, polycarbonate, polysulfone, epoxy resins, silicone resins, diallyl phthalate resins and furan resins.
4. A composite implant material according to claim 3, wherein said resin contains a reinforcing material selected from carbon, silicon carbide, glass, alumina, magnesia, zirconia, tungsten, molybdenum and stainless steel.
5. A process for preparing a composite implant material according to claim 1, comprising forming a sintered apatite material, perforating the sintered apatite material to form holes in a desired configuration therein, and filling or impregnating a thermoplastic or thermosetting resin into said holes.
6. A process according to claim 5, wherein said sintered apatite material is formed using hydroxyapatite.
7. A process according to claim 5, wherein said thermo-plastic or thermosetting resin is selected from the group consisting of polyethylene, polypropylene, polymethyl methacrylate, polyurethane, polyester, acrylonitrile-butadiene-styrene resins, fluorocarbons, polyamides, polyacetals, polycarbonate, polysulfone, epoxy resins, silicone resins, diallyl phthalate resins and furan resins.
8. A process according to claim 5, wherein said sintered apatite material is perforated by mechanical perforation or chemical treatment, or by perforation by means of ultrasonic wave, laser or water jet.
CA302,862A 1977-05-20 1978-05-08 Composite implant materials and process for preparing same Expired CA1107582A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP5755377A JPS53144194A (en) 1977-05-20 1977-05-20 Compound implanted material and making method thereof
JP57553/77 1977-05-20

Publications (1)

Publication Number Publication Date
CA1107582A true CA1107582A (en) 1981-08-25

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Family Applications (1)

Application Number Title Priority Date Filing Date
CA302,862A Expired CA1107582A (en) 1977-05-20 1978-05-08 Composite implant materials and process for preparing same

Country Status (5)

Country Link
US (1) US4222128A (en)
JP (1) JPS53144194A (en)
CA (1) CA1107582A (en)
DE (1) DE2821354C2 (en)
GB (1) GB1594428A (en)

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DE2821354A1 (en) 1978-11-23

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