WO2019034207A2 - Procédé de réalisation d'une couche biocompatible sur une surface d'implant - Google Patents

Procédé de réalisation d'une couche biocompatible sur une surface d'implant Download PDF

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Publication number
WO2019034207A2
WO2019034207A2 PCT/DE2018/100708 DE2018100708W WO2019034207A2 WO 2019034207 A2 WO2019034207 A2 WO 2019034207A2 DE 2018100708 W DE2018100708 W DE 2018100708W WO 2019034207 A2 WO2019034207 A2 WO 2019034207A2
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WO
WIPO (PCT)
Prior art keywords
layer
implant
implant surface
peek
biopolymer
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PCT/DE2018/100708
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German (de)
English (en)
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WO2019034207A3 (fr
Inventor
Albrecht Berg
Matthias Schnabelrauch
Jürgen Weisser
Andreas Pfuch
Oliver Beier
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Verein zur Förderung von Innovationen durch Forschung, Entwicklung und Technologietransfer e.V. (Verein INNOVENT e.V.)
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Publication of WO2019034207A2 publication Critical patent/WO2019034207A2/fr
Publication of WO2019034207A3 publication Critical patent/WO2019034207A3/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
    • A61L27/28—Materials for coating prostheses
    • A61L27/34—Macromolecular materials
    • 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
    • A61L27/14—Macromolecular materials
    • A61L27/18—Macromolecular materials 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
    • A61L2400/00—Materials characterised by their function or physical properties
    • A61L2400/18—Modification of implant surfaces in order to improve biocompatibility, cell growth, fixation of biomolecules, e.g. plasma treatment
    • 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
    • A61L2420/00—Materials or methods for coatings medical devices
    • A61L2420/02—Methods for coating medical devices
    • 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
    • A61L2420/00—Materials or methods for coatings medical devices
    • A61L2420/08—Coatings comprising two or more layers

Definitions

  • the implants used today are, in most cases, materials made of metals, metal alloys, plastics, ceramics and combinations of such materials. For example, since 1995, disc prostheses made of titanium alloys have been used. Especially for titanium implants, both very good fusion results and direct postoperative stability can be achieved. Histologically, at the contact point of the vertebral body and cage, contact osteogenesis occurs with adhesion of osteophytes to the titanium surface.
  • a major disadvantage of metal implants compared to natural bone is their relative hardness. While human bone has an E-modulus of 6-25 kN / mm 2 , titanium has a much higher modulus of elasticity of 105 kN / mm 2 .
  • PEEK polyetheretherketone
  • hydroxyapatite has very good biocompatibility and osteoconduction properties modified PEEK surfaces in vivo and in vitro with respect to cell adhesion, morphology, proliferation, differentiation and bone-implant-contact ratio remarkably improves with a hydroxyapatite coating.
  • Hydroxylapatite coatings are critically discussed in their clinical value due to the previously insufficiently clarified biological and mechanical long-term stability, despite experimentally proven benefits.
  • BLOEBAUM et al. Who studied explanted hip endoprosthesis elements, the release of HA particles from the ceramic-substrate composite can lead to foreign body reactions and osteolysis and hence failure of the prosthesis [Bloebaum, R.D .; Beeks, D .; Dorr, L.D .; Savory, CG .; DuPont, J.A .; Hofman, A.A .: Clin Orthop. 1994, 298, 19-26].
  • HA-coated implants proved to be more susceptible to the development of severe inflammation from bacterial contamination than pure titanium implants [Oosterbos, C.J.M .; Vogely, H.C .; Nijhof, M.W .; Fleer, A .; Verbout, A.J .; Tonino, A.J .: J Biomed Mater Res. 2002, 60, 339-342].
  • titanium and titanium dioxides are very well suited as PEEK coating material. Studies consistently show positive results regarding the significant increase in osteoblast adhesion and cell spreading.
  • Another method for surface modification is the plasma treatment of the PEEK surface.
  • the commonly used plasma modifications are O 2 plasma, NH 4 plasma, N 2 / O 2 plasma, CH O 1 plasma, NH 4 / Ar plasma, H 2 / Ar plasma.
  • Two-plasma-phase PEEK surfaces (microwave plasma in NhVAr, followed by microwave plasma in H 2 / Ar) and investigated the proliferation and differentiation of primary fibroblasts and osteoblasts [Briem, D .; Strametz, S .; Schröder K .; Meen, NM; Lehmann, W .; Linhart, W .; Ohl, A .; Rueger, JM: J. Mater. Be. Mater. Med. 2005, 16, 671-677].
  • the results showed that the osteogenic activity of the osteoblasts on the treated PEEK surface corresponded to the activity on the tissue culture polystyrene material (TCPS) and that the cell proliferation of the fibroblasts could be stimulated or suppressed.
  • TCPS tissue culture polystyrene material
  • Patent WO 2008/142302 A1 describes a method for the production of a fiber-reinforced PEEK implant with a shell made of a biodegradable polymer.
  • Patent GB 2 496 168 A and US Patent US 2009/0276053 A1 disclose a PEEK carbon reinforced joint sheath and a skeleton system support which are coated with a layer of hydroxyapatite.
  • the patent JP 2009-101318 A shows how the surface of a PEEK implant coated with phosphorylcholine groups to achieve the same effect of hydrophilization.
  • PEEK implants with a multilayer coating of carbon, nitrogen and silicon is described in EP 2 526 977 B1.
  • the layers are produced under an argon atmosphere by means of chemical vapor deposition (plasma).
  • Patent WO 2014/060591 A1 describes the coating of plastics (PEK, PEEK, polyarylsiloxanes) with bone substitute material (HA). By short Melting of the plastic surface leads to a penetration of the bone substitute material with the plastic.
  • EP 2 332 589 A2 describes a method for producing plastic implants (PEEK), in which the implant is coated with an intermediate layer of a non-porous metal and a bone growth promoting layer of metal (titanium, tantalum), porous metal or calcium phosphate.
  • a bone growth promoting layer of metal titanium, tantalum
  • porous metal calcium phosphate.
  • Various substances can be introduced into the cover layer, such as bone substrate, growth factors, bioactive substances and antibiotics.
  • the implant consists of a plastic foil, e.g. PEEK.
  • the implant may be coated on the bone-facing side with a metal (titanium) or titanium particles may be introduced into the implant surface.
  • the cartilage-facing side may be coated with a hydrogel.
  • Suitable coating materials are hard-degradable hydrophilic polymers, for example polyacrylic acid and derivatives thereof, such as polymethacrylic acid, polyacrylamide, polyacrylonitrile, polyacrylic esters,
  • Polyhydroxyethyl methacrylates polyvinylpyrrolidone (PVP), polyurethanes, high molecular weight polyvinyl alcohol.
  • the invention has for its object to provide a way whereby the positive properties of PEEK can be improved as implant material in terms of Einwachs , biocompatibility and resorbability of the coating.
  • the object is achieved with a method for producing a biocompatible layer on an implant surface of an implant consisting of polyetheretherketone by first providing the implant surface with hydroxyl groups by reduction of the keto group, then a coupling layer by means of a coupling reagent selected from the substance class of the mono-polyisocyanates is applied by attachment via urethane bonds to the hydroxyl groups of the implant surface and finally a biopolymer layer is made up by means of a modified biopolymer selected from the substance classes of polysaccharides and / or glycosaminoglycans, by attaching to the coupling layer via urethane and / or urea bonds.
  • an SiO x coating takes place by means of chemical vapor deposition at atmospheric pressure (atmospheric pressure plasma: APCVD - atmospheric pressure plasma chemical vapor deposition or CCVD - combustion chemical vapor deposition), which represents a novel method for PEEK surface coating. It acts as a pre-activation for the covalent fixation of the biopolymer or oligoester layer and as the first functionalization step of the PEEK surface.
  • the layer thickness of the SiO x layer may be between 10 and 1000 nm, preferably between 10 and 200 nm.
  • the individual components are present separately from one another.
  • Non-crosslinkable components based on biopolymers and biopolymer derivatives include: dextran, chitosan, sodium alginate, hyaluronic acid, chondroitin sulfate, levan, cellulose and polyglycerol as a synthetic product. These biopolymers can carry additional functional groups such as amino groups, ammonium groups with different chain lengths of the substituents (CrCl 6 ), carboxymethyl, carboxyethyl groups and hydroxypropyl functionalities.
  • aminodextran aminolevan, aminohyaluronic acid, carboxyethyldextran, hydroxypropylchitosan, trimethylaminochitosan, aminocellulose, carboxymethylhyaluronic acid, methylaminoalginate.
  • a first formulation is a monomer of the general structural formula
  • R is a substituent selected from a group comprising hyaluronic acids, sodium alginates, dextranes, aminodextranes, chitosans, levans, chondroitin sulfates and polyglycerols;
  • Z is a member selected from the group comprising -O-, -NH-, -O-CH 2 -CH 2 -NH-CO-O-, -O-CH 2 -CH 2 -NH-CO-NH -, - O-CH 2 - CH (OH) -CH 2 -O- and -NH-CH (CH 3 ) 2 -CO-NH-; and R is a substituent selected from H and CH 3 .
  • S is a molecule selected from a group comprising ethylene glycol, diethylene glycol, triethylene glycol, 1, 6-hexanediol, 1, 8-octane
  • the significantly improved cell adhesion of the MC3T3-E1 cells (bone precursor cells) on the coated PEEK surfaces compared to the uncoated PEEK surfaces was demonstrated in an adhesion test on the basis of the number of adherent cells. Cell numbers were counted by DAPI staining of the nuclei of the adherent cells using a fluorescence microscope. An increase in cell adhesion on the coated PEEK surfaces of up to 32% was found. In addition, it was found that the nonspecific protein absorption on the modified PEEK surfaces was reduced by up to 28%.
  • the actual SiO x coating is carried out, for example, with the following parameters of the same plasma system:
  • Plasma source-substrate distance 10 mm
  • the SiO x layer may contain antimicrobial agents such as zinc oxide.
  • the proportion of active ingredient is adjusted so that the non-cytotoxic properties of the bonding agent layer are preserved compared to the bone cells.
  • the addition of 0.01% DABCO (1, 4-diazabicyclo [2.2.2] octane) is carried out as a catalyst.
  • the PEEK blanks are pivoted at 23 ° C on a rotary table at about 130 rpm.
  • the PEEK discs are washed three times with acetone, dried in air or in a nitrogen stream and used directly for further reaction.
  • the biopolymer layers are applied by placing them in 10% (w / v) aqueous solutions of the biopolymers (exceptions being the aminocellulose 0.5% (w / v) and the hyaluronic acid derivatives 1% (w / v)) overnight in the refrigerator at 4 ° C.
  • Organosoluble biopolymers such as a modified hydroxypropyl chitosan or levan derivatives are dissolved in anhydrous DMSO.
  • the PEEK discs are washed several times with distilled water and dried in a stream of nitrogen.
  • the coated PEEK discs are stored in the desiccator in the dark.
  • Exemplary Embodiment 4 Enrichment of the Implant Surface with Hydroxyl Groups: To generate hydroxyl groups on the PEEK surface to improve the adhesion of the coupling layer, the following procedure is performed.
  • the cleaned PEEK discs are placed in a 2% sodium borohydride solution (w / v) in dimethyl sulfoxide (1.35 ml per round plate) and stirred for 3 h at 120 ° C. with a KPG stirrer.
  • the PEEK discs are dried for three hours at 50 mbar and 40 ° C in a vacuum oven. After drying, the hydroxyl-containing PEEK discs are stored in a desiccator.
  • the further coating takes place according to the embodiments 2 and 3.
  • the PEEK discs are colonized with 200 ⁇ M MC3T3-E1 cell suspension with a density of 40000 Z / ml (»8000 Z / well, 25000 Z / cm 2 ).
  • the primary suspension is estimated from the approximate density of the preculture bottle.
  • a corresponding cell suspension is prepared by diluting an aliquot Primary suspension to a volume of cell culture medium produced.
  • the cells are added over a 40 ⁇ cell strainer.
  • the cell suspension is controlled by means of a cell counter (Scepter) and corrected by adding primary suspension or nutrient medium.
  • the cell suspension is added to the wells using a multipipette with a sterile Combitip advanced 2.5 ml at medium filling speed in meandering application.
  • the cell suspension is shaken before each refill of the Combitip.
  • the 96-well plate is shaken on a shaker for 4 min at 1000 rpm and emptied by everting, which is lightly tapped on pulp. Subsequently, 200 ⁇ 70% (v / v) ethanol in TBS is placed in each well in TBS and the cells are fixed in the refrigerator for 20 min.

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

Abstract

L'invention concerne un procédé de réalisation d'une couche biocompatible sur une surface d'implant en polyétheréthercétone. L'invention a pour but d'offrir une possibilité d'amélioration des propriétés positives du PEEK en tant que matériau d'implant en termes d'ostéointégration, de biocompatibilité et de résorbabilité du revêtement. A cet effet, l'invention concerne un procédé de réalisation d'une couche biocompatible sur une surface d'implant en polyétheréthercétone, caractérisé en ce que : la surface d'implant est tout d'abord dotée de groupes hydroxyle par réduction du groupe céto ou par application d'un revêtement de SiOx; ensuite une couche de couplage est appliquée à l'aide d'un réactif de couplage sélectionné dans la classe de substances des mono-polyisocyanates, une liaison aux groupes hydroxyle de la surface d'implant s'effectuant par l'intermédiaire de liaisons uréthane; et enfin une couche de biopolymère est appliquée à l'aide d'un biopolymère modifié, sélectionné dans les classes de substances des polysaccharides et/ou des glycosaminoglycanes, une liaison à la couche de couplage s'effectuant par l'intermédiaire de liaisons uréthane et/ou urée. En outre, les oligo-ester-méthacrylates ainsi que les oligo-ester-uréthaneméthacrylates sont réticulés sur la surface d'implant à l'aide de photoinitiateurs.
PCT/DE2018/100708 2017-08-14 2018-08-13 Procédé de réalisation d'une couche biocompatible sur une surface d'implant WO2019034207A2 (fr)

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DE102017118508.9 2017-08-14
DE102017118508.9A DE102017118508B4 (de) 2017-08-14 2017-08-14 Verfahren zur Herstellung einer biokompatiblen Schicht auf einer Implantatoberfläche

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Cited By (5)

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CN112869897A (zh) * 2021-01-14 2021-06-01 南京医科大学附属口腔医院 一种氧化锆种植体表面处理方法
CN113398329A (zh) * 2021-06-08 2021-09-17 广西民族大学 一种聚醚醚酮人工骨骼的表面改性方法
CN113750290A (zh) * 2020-06-03 2021-12-07 深圳先进技术研究院 聚醚醚酮复合植入物及其制备方法和应用
CN114230843A (zh) * 2022-01-11 2022-03-25 季华实验室 一种聚醚醚酮表面改性方法
CN117731832A (zh) * 2024-02-19 2024-03-22 上海珀利医用材料有限公司 一种医用聚醚醚酮复合材料及其制备方法和应用

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CN114989475B (zh) * 2022-05-30 2023-07-18 浙江大学 一种生物功能化表面改性的聚醚醚酮材料的制备方法和产品应用
CN115400267B (zh) * 2022-10-10 2023-03-03 吉林大学 一种负载迷迭香酸的聚醚醚酮复合材料的制备方法和应用

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113750290A (zh) * 2020-06-03 2021-12-07 深圳先进技术研究院 聚醚醚酮复合植入物及其制备方法和应用
WO2021243979A1 (fr) * 2020-06-03 2021-12-09 深圳先进技术研究院 Implant composite de polyéther-éther-cétone, méthode de préparation associée et application associée
CN112869897A (zh) * 2021-01-14 2021-06-01 南京医科大学附属口腔医院 一种氧化锆种植体表面处理方法
CN112869897B (zh) * 2021-01-14 2022-01-25 南京医科大学附属口腔医院 一种氧化锆种植体表面处理方法
CN113398329A (zh) * 2021-06-08 2021-09-17 广西民族大学 一种聚醚醚酮人工骨骼的表面改性方法
CN113398329B (zh) * 2021-06-08 2023-03-14 广西民族大学 一种聚醚醚酮人工骨骼的表面改性方法
CN114230843A (zh) * 2022-01-11 2022-03-25 季华实验室 一种聚醚醚酮表面改性方法
CN117731832A (zh) * 2024-02-19 2024-03-22 上海珀利医用材料有限公司 一种医用聚醚醚酮复合材料及其制备方法和应用
CN117731832B (zh) * 2024-02-19 2024-05-10 上海珀利医用材料有限公司 一种医用聚醚醚酮复合材料及其制备方法和应用

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