CA2548206A1 - Dyed polymethyl methacrylate bone cement and process for its production - Google Patents
Dyed polymethyl methacrylate bone cement and process for its production Download PDFInfo
- Publication number
- CA2548206A1 CA2548206A1 CA002548206A CA2548206A CA2548206A1 CA 2548206 A1 CA2548206 A1 CA 2548206A1 CA 002548206 A CA002548206 A CA 002548206A CA 2548206 A CA2548206 A CA 2548206A CA 2548206 A1 CA2548206 A1 CA 2548206A1
- Authority
- CA
- Canada
- Prior art keywords
- bone cement
- polymethyl methacrylate
- methacrylate bone
- cement according
- coupling agent
- 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.)
- Granted
Links
- 239000002639 bone cement Substances 0.000 title claims abstract 15
- 229920003229 poly(methyl methacrylate) Polymers 0.000 title claims abstract 15
- 239000004926 polymethyl methacrylate Substances 0.000 title claims abstract 15
- 238000000034 method Methods 0.000 title claims 2
- 239000007822 coupling agent Substances 0.000 claims abstract 15
- 239000000975 dye Substances 0.000 claims abstract 12
- 239000002245 particle Substances 0.000 claims abstract 10
- 239000000203 mixture Substances 0.000 claims abstract 8
- 229920000642 polymer Polymers 0.000 claims abstract 8
- 239000000843 powder Substances 0.000 claims abstract 6
- 230000002209 hydrophobic effect Effects 0.000 claims abstract 5
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 3
- 239000002872 contrast media Substances 0.000 claims 3
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical class CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 claims 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims 2
- 125000005396 acrylic acid ester group Chemical group 0.000 claims 2
- -1 aliphatic alcohols Chemical class 0.000 claims 2
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical class CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims 2
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims 2
- 102000004169 proteins and genes Human genes 0.000 claims 2
- 108090000623 proteins and genes Proteins 0.000 claims 2
- 229910001928 zirconium oxide Inorganic materials 0.000 claims 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims 1
- UBEIMDKGOYBUKT-FLIQGJDUSA-N 1,2,3-trilinolenoylglycerol Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC UBEIMDKGOYBUKT-FLIQGJDUSA-N 0.000 claims 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims 1
- SGHZXLIDFTYFHQ-UHFFFAOYSA-L Brilliant Blue Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 SGHZXLIDFTYFHQ-UHFFFAOYSA-L 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 claims 1
- UPYKUZBSLRQECL-UKMVMLAPSA-N Lycopene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1C(=C)CCCC1(C)C)C=CC=C(/C)C=CC2C(=C)CCCC2(C)C UPYKUZBSLRQECL-UKMVMLAPSA-N 0.000 claims 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims 1
- FWCCXEACMBKDSC-HATLBPGASA-N OCCO.CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O.CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O.CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O Chemical compound OCCO.CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O.CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O.CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O FWCCXEACMBKDSC-HATLBPGASA-N 0.000 claims 1
- 239000005642 Oleic acid Substances 0.000 claims 1
- 235000019483 Peanut oil Nutrition 0.000 claims 1
- NKSOSPOXQKNIKJ-CLFAGFIQSA-N Polyoxyethylene dioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCOC(=O)CCCCCCC\C=C/CCCCCCCC NKSOSPOXQKNIKJ-CLFAGFIQSA-N 0.000 claims 1
- 235000019484 Rapeseed oil Nutrition 0.000 claims 1
- 235000019486 Sunflower oil Nutrition 0.000 claims 1
- 229930003779 Vitamin B12 Natural products 0.000 claims 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims 1
- 229960001506 brilliant green Drugs 0.000 claims 1
- HXCILVUBKWANLN-UHFFFAOYSA-N brilliant green cation Chemical compound C1=CC(N(CC)CC)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](CC)CC)C=C1 HXCILVUBKWANLN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000001746 carotenes Chemical class 0.000 claims 1
- 235000005473 carotenes Nutrition 0.000 claims 1
- 229930002875 chlorophyll Natural products 0.000 claims 1
- 235000019804 chlorophyll Nutrition 0.000 claims 1
- 229940106705 chlorophyll Drugs 0.000 claims 1
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 claims 1
- 235000019805 chlorophyllin Nutrition 0.000 claims 1
- 229940099898 chlorophyllin Drugs 0.000 claims 1
- MPMSMUBQXQALQI-UHFFFAOYSA-N cobalt phthalocyanine Chemical compound [Co+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 MPMSMUBQXQALQI-UHFFFAOYSA-N 0.000 claims 1
- FDJOLVPMNUYSCM-WZHZPDAFSA-L cobalt(3+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(1r,2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2 Chemical compound [Co+3].N#[C-].N([C@@H]([C@]1(C)[N-]\C([C@H]([C@@]1(CC(N)=O)C)CCC(N)=O)=C(\C)/C1=N/C([C@H]([C@@]1(CC(N)=O)C)CCC(N)=O)=C\C1=N\C([C@H](C1(C)C)CCC(N)=O)=C/1C)[C@@H]2CC(N)=O)=C\1[C@]2(C)CCC(=O)NC[C@@H](C)OP([O-])(=O)O[C@H]1[C@@H](O)[C@@H](N2C3=CC(C)=C(C)C=C3N=C2)O[C@@H]1CO FDJOLVPMNUYSCM-WZHZPDAFSA-L 0.000 claims 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 238000004043 dyeing Methods 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 235000011187 glycerol Nutrition 0.000 claims 1
- 229940097275 indigo Drugs 0.000 claims 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 claims 1
- 239000011261 inert gas Substances 0.000 claims 1
- 239000003999 initiator Substances 0.000 claims 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N linoleic acid group Chemical class C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims 1
- 229960004488 linolenic acid Drugs 0.000 claims 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims 1
- 235000021388 linseed oil Nutrition 0.000 claims 1
- 239000000944 linseed oil Substances 0.000 claims 1
- 229940107698 malachite green Drugs 0.000 claims 1
- FDZZZRQASAIRJF-UHFFFAOYSA-M malachite green Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 FDZZZRQASAIRJF-UHFFFAOYSA-M 0.000 claims 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 1
- 239000000312 peanut oil Substances 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 239000002600 sunflower oil Substances 0.000 claims 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 claims 1
- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 claims 1
- 239000011715 vitamin B12 Substances 0.000 claims 1
- 235000019163 vitamin B12 Nutrition 0.000 claims 1
- 150000003722 vitamin derivatives Chemical class 0.000 claims 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
-
- 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
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/14—Macromolecular materials
- A61L27/16—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
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
-
- 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
Abstract
A dyed polymethyl methacrylate bone cement is described which is characterised by at least the surface of the polymer particles of the powder component being coated partially or completely with a mixture of one or several dyes and a hydrophobic, low molecular or oligomeric organic coupling agent, such a quantity of coupling agent being present that the polymer particles can be visually recognised as not having swollen.
Claims (13)
1. Dyed polymethyl methacrylate bone cement of a liquid and a powder component characterised in that at least the surface of the polymer particles of the powder component is partially or completely coated with a mixture of one or several dyes and a hydrophobic low molecular or oligomeric organic coupling agent, such a quantity of coupling agent being present that the polymer particles are visually recognisable as not having swollen.
2. Dyed polymethyl methacrylate bone cement according to claim 1 additionally containing in the powder component barium sulphate and/or zirconium oxide characterised in that the surface of the x-ray contrast agent barium sulphate and/or zirconium oxide or the surface of all the components of the powder component is also partially or completely coated with a mixture of one or several dyes and a hydrophobic low molecular or oligomeric organic coupling agent.
3. Dyed polymethyl methacrylate bone cement according to any one of claims 1 and 2, characterised in that the dye or dyes are dissolved or suspended in the hydro-phobic, low molecular or oligomeric organic coupling agent.
4. Dyed polymethyl methacrylate bone cement according to any one of claims 1-3, characterised in that the mass ratio of dye/dyes to hydrophobic, low molecular or oligomeric organic coupling agent is 1.0 to 0.1 to 1.0 to 10Ø
5. Dyed polymethyl methacrylate bone cement according to any one of claims 1-4, characterised in that the oleic esters and/or elaidic acid esters and/or linoleic acid esters and/or linolenic acid esters of the aliphatic alcohols with 1 to 22 carbon at-oms or oligomers of these esters are present as coupling agents.
6. Dyed polymethyl methacrylate bone cement according to any one of claims 1-5, characterised in that methacrylic acid esters or acrylic acid esters of the aliphatic alcohols with 4 to 16 carbon atoms or oligomers of these methacrylic acid esters or acrylic acid esters with a molecular weight of less than 3,000 g/mole are present as coupling agents.
7. Dyed polymethyl methacrylate bone cement according to any one of claims 1-6, characterised in that oleic acid, elaidic acid, linolenic acid, glycerine trioleat, glycerine elaidinate, glycerine trilinolenate, ethylene glycol dioleinate, ethylene glycol dielaidinate, ethylene glycol trilinolenate and their oligomers are present as coupling agents.
8. Dyed polymethyl methacrylate bone cement according to any one of claims 1-7, characterised in that coupling agents are present which are produced syntheti-cally or partially synthetically and do not contain proteins or decomposition prod-ucts of proteins.
9. Dyed polymethyl methacrylate bone cement according to any one of claims 1-7, characterised in that refined peanut oil, hardened linseed oil, hardened rapeseed oil and sunflower oil are present as coupling agents.
10. Dyed polymethyl methacrylate bone cement according to any one of claims 1-9, characterised in that the coupling agent contains free radical polymerisable dou-ble bonds.
11. Dyed polymethyl methacrylate bone cement according to any one of claims 1-10, characterised in that the mixtures of coupling agent and the dye or the dyes are soluble in methyl methacrylate.
12. Dyed polymethyl methacrylate bone cement according to any one of claims 1-11, characterised in that chlorophyll, chlorophyllin, indigo, malachite green, crystal violet, brilliant blue, brilliant green, copper phthalocyanin, cobalt phthalocyanin, carotene, vitamin B12 and derivatives derived therefrom are present as dyes.
13. Process for dyeing the polymer particles of the powder component of PMMA
bone cement characterised in that the polymer particles or mixtures of polymer particles and the x-ray contrast agent or mixtures of polymer particles, the x-ray contrast agent and the initiator are coated with a liquid or paste-type mixture of the dye or the dyes and the coupling agent by mixing in a temperature range of 0 °C to 50 °C in the presence of air or inert gas in such a way that the layer thickness of the mixture on the coated particles is less than 2 µm and that the coated particles are not caked together.
bone cement characterised in that the polymer particles or mixtures of polymer particles and the x-ray contrast agent or mixtures of polymer particles, the x-ray contrast agent and the initiator are coated with a liquid or paste-type mixture of the dye or the dyes and the coupling agent by mixing in a temperature range of 0 °C to 50 °C in the presence of air or inert gas in such a way that the layer thickness of the mixture on the coated particles is less than 2 µm and that the coated particles are not caked together.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005032110.0 | 2005-07-07 | ||
| DE102005032110A DE102005032110B3 (en) | 2005-07-07 | 2005-07-07 | Colored polymethyl-methacrylate cement to anchor endoprostheses in orthopoedic surgery incorporates a mixture of one or more dyes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2548206A1 true CA2548206A1 (en) | 2007-01-07 |
| CA2548206C CA2548206C (en) | 2010-07-06 |
Family
ID=36746200
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2548206A Expired - Fee Related CA2548206C (en) | 2005-07-07 | 2006-05-25 | Dyed polymethyl methacrylate bone cement and process for its production |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US7569621B2 (en) |
| EP (1) | EP1741455B1 (en) |
| JP (1) | JP4809144B2 (en) |
| CN (1) | CN100586488C (en) |
| AT (1) | ATE531399T1 (en) |
| AU (1) | AU2006202371B2 (en) |
| BR (1) | BRPI0602636B8 (en) |
| CA (1) | CA2548206C (en) |
| DE (1) | DE102005032110B3 (en) |
| DK (1) | DK1741455T3 (en) |
| ES (1) | ES2375725T3 (en) |
| PL (1) | PL1741455T3 (en) |
| PT (1) | PT1741455E (en) |
| ZA (1) | ZA200605568B (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005033210B4 (en) * | 2005-06-22 | 2008-04-30 | Heraeus Kulzer Gmbh | Polymethylmethacrylate bone cement |
| US8415406B2 (en) * | 2005-07-22 | 2013-04-09 | Howmedica Osteonics Corp. | Setting time indicator for acrylic bone cement |
| US20070021526A1 (en) * | 2005-07-22 | 2007-01-25 | Howmedica Osteonics Corp. | Setting time indicator for acrylic bone cement |
| US7754005B2 (en) * | 2006-05-02 | 2010-07-13 | Kyphon Sarl | Bone cement compositions comprising an indicator agent and related methods thereof |
| DE102007050762B3 (en) * | 2007-10-22 | 2009-05-07 | Heraeus Medical Gmbh | Paste polymethyl methacrylate bone cement and its use |
| KR101031864B1 (en) * | 2009-11-06 | 2011-05-02 | (주)인젝타 | Polymer -based bone cement using duality of paste-powder and loading apparatus thereof |
| DE102012022134A1 (en) * | 2012-11-13 | 2014-05-15 | Heraeus Medical Gmbh | Polymethylmethacrylate bone cement |
| ES2773544T3 (en) | 2013-04-08 | 2020-07-13 | Inossia Ab | Acrylic cements for bone augmentation |
| CN105440921A (en) * | 2015-12-30 | 2016-03-30 | 曲少春 | Paint with good light transmission and preparation method of paint |
| DE102016209988A1 (en) * | 2016-06-07 | 2017-12-07 | Heraeus Medical Gmbh | Paste-like two-component polymethyl methacrylate bone cement |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2511122B2 (en) * | 1975-03-14 | 1977-06-08 | PRE-PRODUCT FOR THE PREPARATION OF BONE CEMENT | |
| DE2905878A1 (en) * | 1979-02-16 | 1980-08-28 | Merck Patent Gmbh | IMPLANTATION MATERIALS AND METHOD FOR THEIR PRODUCTION |
| DE3245956A1 (en) * | 1982-12-11 | 1984-06-14 | Beiersdorf Ag, 2000 Hamburg | SURGICAL MATERIAL |
| US5258420A (en) * | 1987-07-30 | 1993-11-02 | Pfizer Hospital Products Group, Inc. | Bone cement for sustained release of substances |
| US4900546A (en) * | 1987-07-30 | 1990-02-13 | Pfizer Hospital Products Group, Inc. | Bone cement for sustained release of substances |
| US6743438B2 (en) * | 1993-10-26 | 2004-06-01 | Pbh, Inc. | Colored contact lenses and method of making same |
| WO1996039107A1 (en) * | 1995-06-06 | 1996-12-12 | Merck & Co., Inc. | Bisphosphonate cement composition to prevent aseptic loosening of orthopedic implant devices |
| DE19641775A1 (en) * | 1996-08-22 | 1998-02-26 | Merck Patent Gmbh | Process for the production of active ingredient-containing bone cements |
| SK15222000A3 (en) * | 1998-04-14 | 2001-03-12 | Hassan Jomaa | Use of organophosphoric compounds for the therapeutic and preventative treatment of infections |
| US6642285B1 (en) * | 1999-02-02 | 2003-11-04 | Robert Mathys Stiftung | Implant comprising calcium cement and hydrophobic liquid |
| ES2269973T3 (en) * | 2003-02-13 | 2007-04-01 | Synthes Ag Chur | INJECTABLE MIXTURE TO REPLACE A BEAR FABRIC. |
| US20060062825A1 (en) * | 2004-04-19 | 2006-03-23 | Maria Maccecchini | Method of implanting a sterile, active agent-coated material and composition made according to same |
| DE102005033210B4 (en) * | 2005-06-22 | 2008-04-30 | Heraeus Kulzer Gmbh | Polymethylmethacrylate bone cement |
-
2005
- 2005-07-07 DE DE102005032110A patent/DE102005032110B3/en not_active Expired - Fee Related
-
2006
- 2006-05-20 ES ES06010459T patent/ES2375725T3/en active Active
- 2006-05-20 AT AT06010459T patent/ATE531399T1/en active
- 2006-05-20 DK DK06010459.3T patent/DK1741455T3/en active
- 2006-05-20 PT PT06010459T patent/PT1741455E/en unknown
- 2006-05-20 PL PL06010459T patent/PL1741455T3/en unknown
- 2006-05-20 EP EP06010459A patent/EP1741455B1/en not_active Not-in-force
- 2006-05-25 CA CA2548206A patent/CA2548206C/en not_active Expired - Fee Related
- 2006-06-02 AU AU2006202371A patent/AU2006202371B2/en not_active Ceased
- 2006-06-23 CN CN200610095919A patent/CN100586488C/en not_active Expired - Fee Related
- 2006-07-05 BR BRPI0602636A patent/BRPI0602636B8/en not_active IP Right Cessation
- 2006-07-06 JP JP2006186643A patent/JP4809144B2/en not_active Expired - Fee Related
- 2006-07-06 ZA ZA200605568A patent/ZA200605568B/en unknown
- 2006-07-07 US US11/483,339 patent/US7569621B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| ZA200605568B (en) | 2007-09-26 |
| CN1891306A (en) | 2007-01-10 |
| JP2007014778A (en) | 2007-01-25 |
| PT1741455E (en) | 2012-02-01 |
| US7569621B2 (en) | 2009-08-04 |
| BRPI0602636A (en) | 2007-03-06 |
| CN100586488C (en) | 2010-02-03 |
| DE102005032110B3 (en) | 2006-08-17 |
| BRPI0602636B8 (en) | 2021-06-22 |
| ATE531399T1 (en) | 2011-11-15 |
| US20070031469A1 (en) | 2007-02-08 |
| JP4809144B2 (en) | 2011-11-09 |
| AU2006202371B2 (en) | 2008-08-21 |
| EP1741455B1 (en) | 2011-11-02 |
| AU2006202371A1 (en) | 2007-01-25 |
| BRPI0602636A8 (en) | 2017-12-12 |
| PL1741455T3 (en) | 2012-03-30 |
| ES2375725T3 (en) | 2012-03-05 |
| BRPI0602636B1 (en) | 2018-05-22 |
| DK1741455T3 (en) | 2012-02-06 |
| EP1741455A2 (en) | 2007-01-10 |
| CA2548206C (en) | 2010-07-06 |
| EP1741455A3 (en) | 2010-01-13 |
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