EP2291203A2 - Pâte de pmma - Google Patents
Pâte de pmmaInfo
- 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- Withdrawn
Links
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims abstract description 70
- 239000004926 polymethyl methacrylate Substances 0.000 claims abstract description 70
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000002639 bone cement Substances 0.000 claims abstract description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims description 11
- 239000011256 inorganic filler Substances 0.000 claims description 4
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 4
- 239000012766 organic filler Substances 0.000 claims description 4
- 239000003999 initiator Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 238000011049 filling Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 2
- 239000004568 cement Substances 0.000 description 26
- 238000012360 testing method Methods 0.000 description 14
- 239000000178 monomer Substances 0.000 description 10
- 239000000843 powder Substances 0.000 description 9
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 7
- 239000003242 anti bacterial agent Substances 0.000 description 5
- 229940088710 antibiotic agent Drugs 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 3
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 238000013001 point bending Methods 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 210000000988 bone and bone Anatomy 0.000 description 2
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- KOFBVFFPLADGGO-DUSUDKPKSA-N (3r,4s,5r,6r)-6-[(1r,2r)-1-amino-2-hydroxypropyl]oxane-2,3,4,5-tetrol Chemical compound C[C@@H](O)[C@@H](N)[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O KOFBVFFPLADGGO-DUSUDKPKSA-N 0.000 description 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 1
- 229930182566 Gentamicin Natural products 0.000 description 1
- 238000003109 Karl Fischer titration Methods 0.000 description 1
- KGZHFKDNSAEOJX-WIFQYKSHSA-N Ramoplanin Chemical compound C([C@H]1C(=O)N[C@H](CCCN)C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C)C(=O)N[C@H](C(=O)O[C@@H]([C@@H](C(N[C@@H](C(=O)N[C@H](CCCN)C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N1)[C@H](C)O)C=1C=CC(O)=CC=1)C=1C=CC(O)=CC=1)[C@@H](C)O)C=1C=CC(O)=CC=1)=O)NC(=O)[C@H](CC(N)=O)NC(=O)\C=C/C=C/CC(C)C)C(N)=O)C=1C=C(Cl)C(O)=CC=1)C=1C=CC(O)=CC=1)[C@@H](C)O)C=1C=CC(O[C@@H]2[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O[C@@H]2[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=CC=1)C1=CC=CC=C1 KGZHFKDNSAEOJX-WIFQYKSHSA-N 0.000 description 1
- 108010053950 Teicoplanin Proteins 0.000 description 1
- 108010059993 Vancomycin Proteins 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229960004821 amikacin Drugs 0.000 description 1
- LKCWBDHBTVXHDL-RMDFUYIESA-N amikacin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O LKCWBDHBTVXHDL-RMDFUYIESA-N 0.000 description 1
- 239000002647 aminoglycoside antibiotic agent Substances 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- DDTDNCYHLGRFBM-YZEKDTGTSA-N chembl2367892 Chemical compound CC(=O)N[C@H]1[C@@H](O)[C@H](O)[C@H](CO)O[C@H]1O[C@@H]([C@H]1C(N[C@@H](C2=CC(O)=CC(O[C@@H]3[C@H]([C@H](O)[C@H](O)[C@@H](CO)O3)O)=C2C=2C(O)=CC=C(C=2)[C@@H](NC(=O)[C@@H]2NC(=O)[C@@H]3C=4C=C(O)C=C(C=4)OC=4C(O)=CC=C(C=4)[C@@H](N)C(=O)N[C@H](CC=4C=C(Cl)C(O5)=CC=4)C(=O)N3)C(=O)N1)C(O)=O)=O)C(C=C1Cl)=CC=C1OC1=C(O[C@H]3[C@H]([C@@H](O)[C@H](O)[C@H](CO)O3)NC(C)=O)C5=CC2=C1 DDTDNCYHLGRFBM-YZEKDTGTSA-N 0.000 description 1
- 229960003405 ciprofloxacin Drugs 0.000 description 1
- 229960002227 clindamycin Drugs 0.000 description 1
- KDLRVYVGXIQJDK-AWPVFWJPSA-N clindamycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@H](C)Cl)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 KDLRVYVGXIQJDK-AWPVFWJPSA-N 0.000 description 1
- 229960002488 dalbavancin Drugs 0.000 description 1
- 108700009376 dalbavancin Proteins 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 210000000501 femur body Anatomy 0.000 description 1
- 210000002436 femur neck Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229940124307 fluoroquinolone Drugs 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229960002518 gentamicin Drugs 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229960003907 linezolid Drugs 0.000 description 1
- TYZROVQLWOKYKF-ZDUSSCGKSA-N linezolid Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCOCC1 TYZROVQLWOKYKF-ZDUSSCGKSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- -1 moxifloxaxin Chemical compound 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000003910 polypeptide antibiotic agent Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- 229950003551 ramoplanin Drugs 0.000 description 1
- 108010076689 ramoplanin Proteins 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 229960001608 teicoplanin Drugs 0.000 description 1
- 229960000707 tobramycin Drugs 0.000 description 1
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 1
- 229960003165 vancomycin Drugs 0.000 description 1
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
- KGPGQDLTDHGEGT-JCIKCJKQSA-N zeven Chemical compound C=1C([C@@H]2C(=O)N[C@H](C(N[C@H](C3=CC(O)=C4)C(=O)NCCCN(C)C)=O)[C@H](O)C5=CC=C(C(=C5)Cl)OC=5C=C6C=C(C=5O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@H](O5)C(O)=O)NC(=O)CCCCCCCCC(C)C)OC5=CC=C(C=C5)C[C@@H]5C(=O)N[C@H](C(N[C@H]6C(=O)N2)=O)C=2C(Cl)=C(O)C=C(C=2)OC=2C(O)=CC=C(C=2)[C@H](C(N5)=O)NC)=CC=C(O)C=1C3=C4O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O KGPGQDLTDHGEGT-JCIKCJKQSA-N 0.000 description 1
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.
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- General Health & Medical Sciences (AREA)
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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.
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)
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 |
ES2567413T3 (es) | 2012-05-16 | 2016-04-22 | Heraeus Medical Gmbh | Cemento óseo en forma de pasta |
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)
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 |
US7981945B2 (en) * | 2006-03-01 | 2011-07-19 | Poly-Med, Inc. | Antimicrobial, radiopaque, microfiber-reinforced, polymeric methacrylate bone cement |
US8575274B2 (en) * | 2006-07-17 | 2013-11-05 | Syracuse University | Multi-solution bone cements and methods of making the same |
-
2008
- 2008-06-30 DE DE102008064657A patent/DE102008064657A1/de not_active Withdrawn
-
2009
- 2009-06-13 WO PCT/EP2009/004272 patent/WO2010000384A2/fr active Application Filing
- 2009-06-13 EP EP09772084A patent/EP2291203A2/fr not_active Withdrawn
- 2009-06-13 JP JP2011515159A patent/JP2011526171A/ja active Pending
- 2009-06-13 US US13/001,890 patent/US20110112210A1/en not_active Abandoned
- 2009-06-13 CA CA2728880A patent/CA2728880A1/fr not_active Abandoned
- 2009-06-13 AU AU2009266110A patent/AU2009266110A1/en not_active Abandoned
Non-Patent Citations (1)
Title |
---|
See references of WO2010000384A3 * |
Also Published As
Publication number | Publication date |
---|---|
CA2728880A1 (fr) | 2010-01-07 |
US20110112210A1 (en) | 2011-05-12 |
AU2009266110A1 (en) | 2010-01-07 |
WO2010000384A2 (fr) | 2010-01-07 |
DE102008064657A1 (de) | 2010-04-08 |
WO2010000384A3 (fr) | 2010-09-30 |
JP2011526171A (ja) | 2011-10-06 |
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