EP2291203A2 - Pâte de pmma - Google Patents

Pâte de pmma

Info

Publication number
EP2291203A2
EP2291203A2 EP09772084A EP09772084A EP2291203A2 EP 2291203 A2 EP2291203 A2 EP 2291203A2 EP 09772084 A EP09772084 A EP 09772084A EP 09772084 A EP09772084 A EP 09772084A EP 2291203 A2 EP2291203 A2 EP 2291203A2
Authority
EP
European Patent Office
Prior art keywords
pmma
paste
methyl methacrylate
pmma paste
bone cements
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.)
Withdrawn
Application number
EP09772084A
Other languages
German (de)
English (en)
Inventor
Sebastian Vogt
Hubert Buechner
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.)
Heraeus Medical GmbH
Original Assignee
Heraeus Medical GmbH
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
Priority claimed from DE102008030312A external-priority patent/DE102008030312A1/de
Application filed by Heraeus Medical GmbH filed Critical Heraeus Medical GmbH
Publication of EP2291203A2 publication Critical patent/EP2291203A2/fr
Withdrawn legal-status Critical Current

Links

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
    • A61L24/0015—Medicaments; Biocides
    • 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
    • A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
    • A61L24/06—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials obtained 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
    • 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
    • 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
    • A61L2300/41—Anti-inflammatory agents, e.g. NSAIDs
    • 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
    • A61L2300/412—Tissue-regenerating or healing or proliferative agents
    • A61L2300/414—Growth factors
    • 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
    • A61L2300/43—Hormones, e.g. dexamethasone
    • 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 PMMA paste (polymethyl methacrylate paste), their use and containing them paste-like one-component bone cements or bicomponent bone cements.
  • PMMA paste polymethyl methacrylate paste
  • PMMA bone cements have been known for decades and are based on the fundamental work of Sir Charnley (Chamley, J .: Anchorage of the femoral head prosthesis of the shaft of the femur, J. Bone Joint Surg., 42 (1960) 28-30. ). The basic structure of the PMMA bone cements has remained basically the same since then.
  • PMMA bone cements consist of a liquid monomer component and a powder component.
  • the monomer component generally contains the monomer methyl methacrylate and an activator (N, N-dimethyl-p-toluidine) dissolved therein.
  • the powder component consists of one or more polymers which are prepared on the basis of methyl methacrylate and comonomers, such as styrene and methyl acrylate, by polymerization, preferably suspension polymerization, an X-ray opaque and the initiator dibenzoyl peroxide.
  • a plastically deformable dough is formed by swelling the polymers of the powder component in the methyl methacrylate.
  • the activator N 1 N-dimethyl-p-toluidine reacts with the dibenzoyl peroxide, which decomposes to form free radicals.
  • the radicals formed initiate the polymerization of the methyl methacrylate.
  • the viscosity of the cement paste increases until the dough solidifies and hardens.
  • PMMA bone cements Basic mechanical requirements for PMMA bone cements, such as 4-flexural strength, flexural modulus and compressive strength, are described in ISO 5833.
  • the property of the freedom from tackiness of the bone cement is of essential importance.
  • the term tack-free is defined in ISO5833.
  • the tackiness shows for conventional PMMA bone cements, the cement has reached the processing phase after mixing the components by swelling the polymers in the cement powder contained in the cement powder.
  • a PMMA bone cement must be tack-free so that the user can shape and apply the cement.
  • the PMMA bone cement must not stick to the gloves and application aids, such as mixing systems, jars or spatulas.
  • a disadvantage of the conventional PMMA bone cements for the cement producer is that both the powder component and the monomer component have to be prepared in double sterile packaging. This means that at least four sterile packaging materials are required for a bone cement pack.
  • a further disadvantage of the previous PMMA bone cements for the medical user is that the liquid monomer component must be mixed with the powder component immediately before the cement application in a mixing system or in crucibles. In this case, mixing errors can easily occur, which can adversely affect the cement quality. After mixing the monomer component with the powder component, depending on the type of cement, it is necessary to wait a certain time until the cement paste is tack-free and can be applied. Thereafter, the user has a more or less short processing time available in the total endoprostheses can be positioned or bone cavities as in kyphoplasty and vertebroplasty can be filled.
  • the viscosity of the cement dough changes due to the increasing swelling of the polymer particles in the monomer and the progressive polymerization of the monomer.
  • the relatively short processing time is a major disadvantage of the previous bone cements.
  • Particularly disadvantageous are short processing times in kyphoplasty and vertebroplasty. It would be desirable to have a cement, especially for vertebroplasty and kyphoplasty, in which the viscosity of the cement paste remains substantially constant over a period of several minutes during cement application.
  • the object of the invention is therefore to develop a PMMA paste which can be used as starting material for the production of paste-like PMMA bone cements, which can overcome the problems of the known PMMA bone cements.
  • the object of the invention is achieved by a PMMA paste according to claim 1. Advantageous embodiments emerge from the other claims.
  • the PMMA paste according to the invention is composed of a mixture
  • a methyl methacrylate which has a methacrylic acid content of less than 1% and a
  • methyl methacrylate is understood as meaning both pure methyl methacrylate and methyl methacrylate contaminated with small amounts of other monomers such as ethyl methacrylate, propyl methacrylate and styrene, provided that these impurities do not exceed a total content of 5%.
  • the polymethyl methacrylate is at least 80 percent by weight soluble in methyl methacrylate.
  • pastes with a proportion of methyl methacrylate greater than or equal to 50% by weight are autosterly. This means that methyl methacrylate causes a killing of microbial germs in the PMMA paste. Accordingly, preference is given to PMMA pastes in which a weight ratio of 10-50% of polymethyl methacrylate to 50-90% of methyl methacrylate is present.
  • the invention also relates to the use of the above-described PMMA pastes for the production of single-component paste-like bone cements and two-component bone cements.
  • the PMMA paste is mixed with organic and / or inorganic fillers and with radical initiators and / or accelerators for the production of one-component and two-component bone cements.
  • organic and inorganic fillers which do not swell in methyl methacrylate and have a methyl methacrylate uptake of less than 25% are mixed with the PMMA paste.
  • the PMMA paste according to the invention is used for the preparation of an agent for the fixation of total endoprostheses and revision endoprostheses.
  • PMMA paste according to the invention for the production of a self-hardening filling material for vertebroplasty, kyphoplasty and femoral neck suction.
  • the PMMA paste according to the invention can also be used for the production of local drug release systems. So it is z. For example, it is possible to form spherical or bean-shaped implants containing PMMA bone cement prepared from the PMMA paste of the present invention which can be used as local drug delivery systems.
  • antibiotics are, in particular, aminoglycoside antibiotics, glycopeptide antibiotics, fluoroquinolone antibiotics, lincosamide antibiotics and oxazolidinone antibiotics.
  • Preferred are gentamicin, tobramycin, amikacin, teicoplanin, vancomycin, ramoplanin, dalbavancin, moxifloxaxin, ciprofloxacin, lincosamine, clindamycin and linezolid.
  • the paste 2 was prepared analogously to the PMMA paste 1, but a PMMA having a molecular weight of about 700,000 g / mol and a Tg of 100-106 0 C was used.
  • the PMMA concentration was adjusted to 30%.
  • the paste 2 was prepared analogously to the PMMA paste 1, but a PMMA having a molecular weight of about 1200,000 g / mol and a Tg of 100-105 0 C was used.
  • the PMMA concentration was adjusted to 28%.
  • the cement paste was used to produce test specimens for determining the 4-point bending strength and the flexural modulus according to ISO5833 and for testing the Dynstat impact strength.
  • the 4-point flexural strength and the flexural modulus were tested after storage of the test specimens at room temperature after 24 hours and in addition after storage of the test specimens in water at 37 0 C for 24 and 48 hours.
  • the cement paste was used to produce test specimens for determining the 4-point bending strength and the flexural modulus according to ISO5833 and for testing the Dynstat impact strength. After testing the test specimens at room temperature after 24 hours and after storage of the test specimens in water at 37 ° C. for 24 and 48 hours, the 4-point flexural strength and flexural modulus were tested.
  • Paste A 30 g of Paste A were mixed with 30 g of Paste B using a double cartridge system with static mixer attached.
  • the resulting cement dough was immediately tack-free and could be molded over a period of about 7 minutes. This was followed within about 6 minutes, the curing of the cement.
  • the cement paste was used to produce test specimens for determining the 4-point bending strength and the flexural modulus according to ISO5833 and for testing the Dynstat impact strength.
  • the testing of the 4-point flexural strength and the flexural modulus was carried out after storage of the test specimens at room temperature in air and at 37 ° C. in water after 24 hours.

Landscapes

  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Surgery (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Materials For Medical Uses (AREA)

Abstract

La présente invention concerne une pâte de PMMA produite à partir d'une mélange de A méthylméthacrylate ayant une teneur en acide méthacrylique inférieure à 1% et une teneur en eau inférieure à 1%, et B au moins une polyméthylméthacrylate ayant une Tg supérieure à 65 °C et une masse molaire supérieure ou égale à 200000 g/ mol, la composante méthylméthacrylate étant d'une importance telle que la pâte de PMMA est autostérile et le rapport pondéral est de 10-50 % de B pour 50-90 % de A. La pâte de PMMA de l'invention peut être utilisée pour réalisation de ciments osseux pâteux à une ou à deux composantes.
EP09772084A 2008-06-30 2009-06-13 Pâte de pmma Withdrawn EP2291203A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102008030312A DE102008030312A1 (de) 2008-06-30 2008-06-30 PMMA-Paste
PCT/EP2009/004272 WO2010000384A2 (fr) 2008-06-30 2009-06-13 Pâte de pmma

Publications (1)

Publication Number Publication Date
EP2291203A2 true EP2291203A2 (fr) 2011-03-09

Family

ID=41008908

Family Applications (1)

Application Number Title Priority Date Filing Date
EP09772084A Withdrawn EP2291203A2 (fr) 2008-06-30 2009-06-13 Pâte de pmma

Country Status (7)

Country Link
US (1) US20110112210A1 (fr)
EP (1) EP2291203A2 (fr)
JP (1) JP2011526171A (fr)
AU (1) AU2009266110A1 (fr)
CA (1) CA2728880A1 (fr)
DE (1) DE102008064657A1 (fr)
WO (1) WO2010000384A2 (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102010005956B4 (de) * 2010-01-27 2011-09-01 Heraeus Medical Gmbh Dreikomponentenknochenzement und dessen Verwendung
US9265830B2 (en) * 2011-04-20 2016-02-23 Warsaw Orthopedic, Inc. Implantable compositions and methods for preparing the same
DE102011108574A1 (de) * 2011-07-27 2013-01-31 Heraeus Medical Gmbh Kit und Verfahren zur Herstellung von Knochenzement
CA2797904C (fr) 2011-12-20 2015-01-27 Heraeus Medical Gmbh Ciment osseux de type pate
DE102012001637A1 (de) * 2012-01-30 2013-08-01 Heraeus Medical Gmbh Pastenförmiger Knochenzement
DE102012001636A1 (de) * 2012-01-30 2013-08-01 Heraeus Medical Gmbh Pastenförmiger Knochenzement
EP2664349B1 (fr) * 2012-05-16 2016-02-03 Heraeus Medical GmbH Ciment osseux pâteux
DE102012014418A1 (de) * 2012-07-20 2014-01-23 Heraeus Medical Gmbh Pastenförmiger Knochenzement
FR3016641B1 (fr) * 2014-01-22 2020-02-21 Arkema France Procede d'impregnation pour un substrat fibreux fonctionnel, sirop monomere liquide pour le procede d'impregnation, sa methode de polymerisation et article structurel obtenu
DE102014105267A1 (de) 2014-04-14 2015-10-15 Heraeus Medical Gmbh Polymethylmethacrylat-Knochenzement

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5412967A (en) * 1977-06-30 1979-01-31 Kumahira Safe Co System for holding shelf horizontally in electrically driving file and like
US5461124A (en) * 1992-07-24 1995-10-24 Henkel Kommanditgesellschaft Auf Aktien Reactive systems and/or polymer composition for tissue contact with the living body
US5902839A (en) * 1996-12-02 1999-05-11 Northwestern University Bone cement and method of preparation
ITVI20010126A1 (it) * 2001-05-30 2002-11-30 Tecres Spa Cemento osseo radiopaco per uso ortopedico nonche' metodo di realizzazione
FR2870129A1 (fr) * 2004-05-14 2005-11-18 Ceravic Sas Soc Par Actions Si Ciment polymere pour la vertebroplastie percutanee
DE102006006510A1 (de) * 2006-02-10 2007-08-23 Heraeus Kulzer Gmbh Lokales Wirkstofffreisetzungssystem und ein Verfahren zu seiner Herstellung
WO2007106256A2 (fr) * 2006-03-01 2007-09-20 Poly-Med, Inc. Ciment osseux antimicrobien radiopaque à base de polymère de méthacrylate renforcé de microfibres
US8575274B2 (en) * 2006-07-17 2013-11-05 Syracuse University Multi-solution bone cements and methods of making the same

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2010000384A3 *

Also Published As

Publication number Publication date
CA2728880A1 (fr) 2010-01-07
WO2010000384A2 (fr) 2010-01-07
WO2010000384A3 (fr) 2010-09-30
JP2011526171A (ja) 2011-10-06
DE102008064657A1 (de) 2010-04-08
US20110112210A1 (en) 2011-05-12
AU2009266110A1 (en) 2010-01-07

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