ZA200605104B - Polymethylmethacrylate bone cement - Google Patents
Polymethylmethacrylate bone cement Download PDFInfo
- Publication number
- ZA200605104B ZA200605104B ZA200605104A ZA200605104A ZA200605104B ZA 200605104 B ZA200605104 B ZA 200605104B ZA 200605104 A ZA200605104 A ZA 200605104A ZA 200605104 A ZA200605104 A ZA 200605104A ZA 200605104 B ZA200605104 B ZA 200605104B
- Authority
- ZA
- South Africa
- Prior art keywords
- bone cement
- dye
- polymethylmethacrylate bone
- acid esters
- solid component
- Prior art date
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- 239000002639 bone cement Substances 0.000 title claims description 36
- 229920003229 poly(methyl methacrylate) Polymers 0.000 title claims description 29
- 239000004926 polymethyl methacrylate Substances 0.000 title claims description 29
- 239000000306 component Substances 0.000 claims description 40
- 239000000975 dye Substances 0.000 claims description 40
- 239000000178 monomer Substances 0.000 claims description 29
- 239000007788 liquid Substances 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 26
- 239000007787 solid Substances 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- 230000002209 hydrophobic effect Effects 0.000 claims description 9
- 239000000843 powder Substances 0.000 claims description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 7
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- 229920002319 Poly(methyl acrylate) Polymers 0.000 claims description 4
- 125000005396 acrylic acid ester group Chemical group 0.000 claims description 4
- -1 aliphatic alcohols Chemical class 0.000 claims description 4
- 239000004568 cement Substances 0.000 claims description 4
- 150000002888 oleic acid derivatives Chemical class 0.000 claims description 4
- 235000011837 pasties Nutrition 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 235000011187 glycerol Nutrition 0.000 claims description 3
- HBOQXIRUPVQLKX-BBWANDEASA-N 1,2,3-trilinoleoylglycerol Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/C\C=C/CCCCC)COC(=O)CCCCCCC\C=C/C\C=C/CCCCC HBOQXIRUPVQLKX-BBWANDEASA-N 0.000 claims description 2
- 235000000177 Indigofera tinctoria Nutrition 0.000 claims description 2
- 229930003779 Vitamin B12 Natural products 0.000 claims description 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 description 2
- 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 description 2
- 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 description 2
- 239000013078 crystal Substances 0.000 claims description 2
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical class CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 claims description 2
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 claims description 2
- 229940097275 indigo Drugs 0.000 claims description 2
- 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 description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N linoleic acid group Chemical class C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims description 2
- 229940107698 malachite green Drugs 0.000 claims description 2
- 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 description 2
- 229920000193 polymethacrylate Polymers 0.000 claims description 2
- 238000007348 radical reaction Methods 0.000 claims description 2
- 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 description 2
- 239000011715 vitamin B12 Substances 0.000 claims description 2
- 235000019163 vitamin B12 Nutrition 0.000 claims description 2
- 150000003722 vitamin derivatives Chemical class 0.000 claims description 2
- 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical group COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- 235000019483 Peanut oil Nutrition 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 210000000988 bone and bone Anatomy 0.000 description 3
- 229930002875 chlorophyll Natural products 0.000 description 3
- 235000019804 chlorophyll Nutrition 0.000 description 3
- 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 description 3
- 239000000312 peanut oil Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 235000019805 chlorophyllin Nutrition 0.000 description 2
- 229940099898 chlorophyllin Drugs 0.000 description 2
- 239000002872 contrast media Substances 0.000 description 2
- 239000004121 copper complexes of chlorophylls and chlorophyllins Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GONFBOIJNUKKST-UHFFFAOYSA-N 5-ethylsulfanyl-2h-tetrazole Chemical compound CCSC=1N=NNN=1 GONFBOIJNUKKST-UHFFFAOYSA-N 0.000 description 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 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004873 anchoring Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000004161 brilliant blue FCF Substances 0.000 description 1
- 229960001506 brilliant green Drugs 0.000 description 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 description 1
- 150000004651 carbonic acid esters Chemical class 0.000 description 1
- 229940106705 chlorophyll Drugs 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 239000004120 green S Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical class OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 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
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical class C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
PIO5S79 ZA
Polymethylmethacrylate Bone Cement
This invention relates to a polymethylmethacrylate bone cement.
Polymethylmethacrylate bone cements (PMMA bone cements) have been in broad use in medicine for decades for anchoring endoprostheses in bone (Klaus-Dieter Kuhn:
Knochenzemente fur die Endoprothetik: ein aktueller Vergleich der physikalischen und chemischen Eigenschaften handelsiblicher PMMA-Zemente. Springer Verlag Berlin
Heidelberg New York, 2001).
In general, polymethylmethacrylate bone cements are made up of a liquid monomer component and a powder component. The liquid monomer component consists of me- thylmethacrylate and an activator. N,N-dimethyl-p-toluidine is preferably used as activa- tor. The powder component consists of polymethylmethacrylate or polymethyl-co- acrylmethacrylate, an X-ray contrast agent, and a radical initiator. Zirconium dioxide and barium sulfate are customary X-ray contrast agents. Dibenzoylperoxide is preferably used as radical initiator. After mixing the monomer component and powder component, the bone cement hardens within a few minutes by radical polymerization of the mono- mer.
After mixing, customary polymethylmethacrylate bone cements are provided in the form of white to pale-yellow pasty masses. This occasionally makes a visual differentiation between bone cement and bone tissue difficult. However, it is desirable to be able to distinguish the bone cement from the surrounding bone tissue without any difficulty. For this reason, Heraeus
Kulzer has dyed its PMMA bone cements green with chlorophyll for the past approx. 30 years. However, chlorophyll is only very poorly soluble in the methylmethacrylate monomer used in this context. For this reason, refined peanut oil is added to improve 2 SSR/SJ/0S/2006022211
®
P10579 ZA the solubility. The refined peanut oil is free of proteins. However, as with any complex natural product, variations of composition are a problem. No alternatives to refined pea- nut oil have been identified thus far.
Regarding the dyeing of PMMA bone cements, not only the toxicological non- objectionability of the dye, but also the homogeneous distribution of the dye throughout the cement is important. For this reason, bone cements containing dye pigments in their monomer liquid or powder component have not been widely used thus far. In principle, dye pigments are associ- ated with the risk of the dye pigments being released and migrating from the cement matrix. For this reason, it is particularly important for the dye to be distributed homogeneously in the bone cement and firmly enclosed therein.
A need exists for developing a dyed PMMA bone cement. The liquid monomer compo- nent of the PMMA bone cement shall not contain any complex natural products as solu- bilizer for dyes that are insoluble or only poorly soluble in methylmethacrylate. The liquid monomer component shall contain a homogeneously distributed dye that is dissolved such as to be translucent.
The invention provides a bone cement having a liquid monomer component and a solid component, wherein the cement exhibits the following characteristics: - a dye/dye mixture that is insoluble or poorly soluble in methacrylic acid methyles- ter and a synthetically produced, protein-free, hydrophobic, low molecular or oli- gomeric solubilizer for the dye or dye mixture are dissolved in the monomer lig- uid, - the monomer liquid is translucent at room temperature; and - a dye/dye mixture that is insoluble or poorly soluble in methacrylic acid methyles- ter and a synthetically produced, protein-free, hydrophobic, low 3 SSR/SJ/0S/2006022211
P10579 ZA molecular or oligomeric solubilizer are homogeneously distributed in the polyme- thacrylate or polymethylacrylate of the solid component.
The solid component may be in the form of a powder. The solubilizer may be liquid or pasty at room temperature.
Preferably, 0.001-1.00 mass percent of a dye or dye mixture that is insoluble or poorly soluble in methacrylic acid methyl ester and 0.001-2.00 mass percent of a synthetically produced, protein-free, hydrophobic, low-molecular or oligomeric solubilizer for the dye or dye mixture are dissolved in the monomer liquid.
Preferably, 0.001-1.00 mass percent of a dye or dye mixture that is insoluble or poorly soluble in methacrylic acid methyl ester and 0.001-2.00 mass percent of a synthetically produced, protein-free, hydrophobic, low-molecular or oligomeric solubilizer that is liquid or pasty at room temperature are homogeneously dissolved in the polymethacrylate or polymethylacrylate of the powder component.
In this context, the invention also encompasses the use of copolymers produced by po- lymerization of acrylic acid esters and/or methacrylic acid esters and styrene or styrene derivatives.
Bone cements according to the invention can, in addition, contain agents such as anti- biotics - or be free of such agents. ltis also feasible to use two synthetically produced, protein-free, hydrophobic, low mo- lecular or oligomeric solubilizers in order to be able to dissolve a dye in the monomer liquid.
It is useful for the dye/dye mixture and the synthetically produced, protein-free, hydro- phobic, low molecular or oligomeric solubilizer to form soluble adducts with the dye/dye mixture in the monomer liquid. 4 SSR/SJ/0S/2006022211
PL0S79 ZA
Also included in the scope of the invention is adduct formation based on non-polar interactions and the formation of adducts by addition of amino groups or thiol groups to double bonds in terms of a Michael addition is particularly. Also included in the scope of the invention is the formation of adducts by covalent linking by means of the formation of carbonic acid amides, carbonic acid esters, ethers, azomethines, and chelates.
In addition, it is useful that oleic acid 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 atoms or oligomers of these oleic acid esters are preferred as solubilizer.
It is useful 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 with a molecu- lar mass of less than 3,000 g/mol are preferred as solubilizers. Also included in the scope of the invention is the use of maleic acid esters, fumaric acid esters, itaconic acid esters, and sorbic acid esters as solubilizer.
Furthermore, it is useful that glycerine trioleate, glycerine trilinolate, glycerine trilinole- nate, and glycerine trielaidinate are preferred as solubilizer. Also included in the scope of the invention is the use of mixed glycerine esters of these unsaturated fatty acids.
It is also useful for the solubilizer to contain double bonds that can be polymerized by radical reaction. One or more double bonds can be present in the solubilizer. The par- ticular advantage is that the solubilizer participates in the radical polymerization of the methylmethacrylate during the hardening of the PMMA bone cement and thus is incor- porated into the polymer chains thus generated. This effectively precludes any migration of the solubilizer from the cured PMMA bone cement.
Preferred dyes are chlorophyll, indigo, malachite green, crystal violet, copper phthalo- cyanine, cobalt phthalocyanine, vitamin B12, and derivatives thereof. Other green, blue, violet or red dyes approved for use in medicine can be used as well. Particularly pre- 5 SSR/SJ/0S/2006022211
P10379 ZA ferred is the use of chlorophyllin (E141), Brilliant green BS (E142), and Brilliant blue (E133).
The invention will now be described by way of the following non-limiting examples.
Example 1
A total of 1.00 g copper chlorophyllin (dye E141) and 1.00 g oleic acid ethyl ester (Ph.Eur., Fluka) and 18.00 g methylmethacrylate (Fluka) are mixed under stirring for 10 minutes in a 100 ml Erlenmeyer flask. This produces a dark green, clear solution. Then, 980 g methylmethacrylate are added to this solution. This produces a translucent solu- tion that is strongly green in color. The solution is then transferred to 20 ml vials and the vials are sealed by melting. The vials are provided to serve as monomer component for a PMMA bone cement.
Example 2
Dibenzoylperoxide was added to a green methyimethacrylate solution prepared accord- ing to Example 1, and polymerized at 60 °C in water under vigorous stirring to form polymer beads. The beaded polymer thus produced is then mixed with 30.0 mass per- cent zirconium dioxide and 1.0 mass percent dibenzoylperoxide and provided as pow- der component for a PMMA bone cement.
It is to be appreciated, that the invention is not limited to any particular embodiment as hereinbefore generally described or illustrated. 6 SSR/SJ/0S/2006022211
Claims (14)
1. A polymethylmethacrylate bone cement with a liquid monomer component and a solid component, wherein the cement exhibits the following characteristics: - a dye/dye mixture that is insoluble or poorly soluble in methacrylic acid methyles- ter and a synthetically produced, protein-free, hydrophobic, low molecular or oli- gomeric solubilizer for the dye or dye mixture are dissolved in the monomer lig- uid; - the monomer liquid is translucent at room temperature; and - a dye/dye mixture that is insoluble or poorly soluble in methacrylic acid methyles- ter and a synthetically produced, protein-free, hydrophobic, low molecular or oligomeric solubilizer are homogeneously distributed in the polyme- thacrylate or polymethylacrylate of the solid component.
2. A polymethylmethacrylate bone cement as claimed in claim 1, wherein the dye/dye mixture is present at a concentration of 0.001-1.00 mass percent and the solubilizer is present at a concentration of 0.001-2.00 mass percent in the monomer liquid or, respectively, in the polymethacrylate or polymethylacrylate.
3. A polymethylmethacrylate bone cement as claimed in claim 1, wherein the solubi- lizer is liquid at room temperature.
4, A polymethylmethacrylate bone cement as claimed in claim 1, wherein the solubi- lizer is pasty at room temperature.
5. A polymethylmethacrylate bone cement with a liquid monomer component and a solid component as claimed in any one of the claims 1-4, wherein the dye/dye mixture and the synthetically produced, protein-free, hydrophobic, low molecular or oligomeric solubilizer form soluble adducts with the dye/dye mixture in the monomer liquid. 7 SSR/SJ/0S/2006022211
P105379 ZA
6. A polymethyimethacrylate bone cement with a liquid monomer component and a solid component as claimed in any one of the claims 1-5, wherein oleic acid 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 atoms or oligomers of these oleic acid esters are used as solubilizer.
7. A polymethylmethacrylate bone cement with a liquid monomer component and a solid component as claimed in any one of the claims 1-5, wherein methacrylic acid esters or acrylic acid esters of the aliphatic alcohols with 4 to 16 carbon at- oms or oligomers of these methacrylic acid esters or acrylic acid esters with a molecular mass of less than 3,000 g/mol are used as solubilizers.
8. A polymethylmethacrylate bone cement with a liquid monomer component and a solid component as claimed in any one of the claims 1-5, wherein glycerine trioleate, glycerine trilinolate, glycerine trilinolenate, and glycerine trielaidinate are used as solubilizer.
9. A polymethylmethacrylate bone cement with a liquid monomer component and a solid component as claimed in any one of the claims 1-8, wherein the solubilizer contains double bonds that can be polymerized by radical reaction.
10. A polymethylmethacrylate bone cement with a liquid monomer component and a solid component as claimed in any one of the claims 1-9, wherein compounds se- lected from the group including: chlorophyliin, indigo, malachite green, crystal violet, copper phthalocyanine, cobalt phthalocya- nine, vitamin B12, and derivatives thereof are used as dyes.
11. A polymethylmethacrylate bone cement with a liquid monomer component and a solid component as claimed in any one of the claims 1-10, wherein the solid com- ponent is in the form of a powder. 8 SSR/SJ/0S/2006022211
P10579 ZA
12. A polymethylmethacrylate bone cement with a liquid monomer component and a solid component according to the invention, as hereinbefore generally described.
13. A polymethylmethacrylate bone cement with a liquid monomer component and a solid component as specifically described in the aforegoing examples.
14. A polymethylmethacrylate bone cement with a liquid monomer component and a solid component including any new and inventive integer or combination of integers, substantially as herein described. DATED AT PRETORIA THIS 21°" DAY OF JUNE 2006. HAHN & HAHN INC. APPLICANT'S ATTORNEYS 9 SSR/SJ/0S/2006022211
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005029218 | 2005-06-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200605104B true ZA200605104B (en) | 2007-12-27 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200605104A ZA200605104B (en) | 2005-06-22 | 2006-06-21 | Polymethylmethacrylate bone cement |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN100579587C (en) |
| ZA (1) | ZA200605104B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2773544T3 (en) * | 2013-04-08 | 2020-07-13 | Inossia Ab | Acrylic cements for bone augmentation |
-
2006
- 2006-06-21 ZA ZA200605104A patent/ZA200605104B/en unknown
- 2006-06-21 CN CN200610094667A patent/CN100579587C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1883717A (en) | 2006-12-27 |
| CN100579587C (en) | 2010-01-13 |
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