WO1996032970A1 - Adhesion promotion of orthopaedic implants - Google Patents
Adhesion promotion of orthopaedic implants Download PDFInfo
- Publication number
- WO1996032970A1 WO1996032970A1 PCT/US1996/005079 US9605079W WO9632970A1 WO 1996032970 A1 WO1996032970 A1 WO 1996032970A1 US 9605079 W US9605079 W US 9605079W WO 9632970 A1 WO9632970 A1 WO 9632970A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- coupling agent
- cement
- acrylate
- silane
- exposed
- Prior art date
Links
- 239000007943 implant Substances 0.000 title claims abstract description 14
- 239000004568 cement Substances 0.000 claims abstract description 32
- 238000000034 method Methods 0.000 claims abstract description 27
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 23
- 239000011248 coating agent Substances 0.000 claims abstract description 12
- 238000000576 coating method Methods 0.000 claims abstract description 11
- 239000000919 ceramic Substances 0.000 claims abstract description 4
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 4
- 150000004706 metal oxides Chemical class 0.000 claims abstract description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 4
- 239000007822 coupling agent Substances 0.000 claims description 26
- 229910000077 silane Inorganic materials 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- -1 alkoxy silane Chemical compound 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000005647 linker group Chemical group 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 238000002525 ultrasonication Methods 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical group CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 238000007598 dipping method Methods 0.000 claims description 2
- 230000002708 enhancing effect Effects 0.000 claims description 2
- YFCGLJNSEZMEQA-UHFFFAOYSA-N ethenyl-tris(2-methoxyethyl)silane Chemical compound COCC[Si](CCOC)(CCOC)C=C YFCGLJNSEZMEQA-UHFFFAOYSA-N 0.000 claims 1
- 239000006087 Silane Coupling Agent Substances 0.000 abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 18
- 239000004926 polymethyl methacrylate Substances 0.000 description 18
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 17
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 8
- 229910001069 Ti alloy Inorganic materials 0.000 description 7
- 210000000988 bone and bone Anatomy 0.000 description 5
- 229910001092 metal group alloy Inorganic materials 0.000 description 5
- 230000035882 stress Effects 0.000 description 5
- 229910045601 alloy Inorganic materials 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- 239000002639 bone cement Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 229910000684 Cobalt-chrome Inorganic materials 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000010952 cobalt-chrome Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- MWGMEGAYPPQWFG-UHFFFAOYSA-N [SiH4].OC(=O)C=C Chemical compound [SiH4].OC(=O)C=C MWGMEGAYPPQWFG-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 230000008512 biological response Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000001356 surgical procedure Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 2
- 238000002604 ultrasonography Methods 0.000 description 2
- 0 CC(C(OCCOC(NCCCS(C)=*=C)=O)=O)=C Chemical compound CC(C(OCCOC(NCCCS(C)=*=C)=O)=O)=C 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 229910001182 Mo alloy Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- AHGFXGSMYLFWEC-UHFFFAOYSA-N [SiH4].CC(=C)C(O)=O Chemical compound [SiH4].CC(=C)C(O)=O AHGFXGSMYLFWEC-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 210000001624 hip Anatomy 0.000 description 1
- 210000004394 hip joint Anatomy 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 210000004197 pelvis Anatomy 0.000 description 1
- 238000004393 prognosis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- 230000003442 weekly effect Effects 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
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/28—Materials for coating prostheses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Definitions
- This invention relates to the treatment of orthopaedic implant alloys to improve the adhesion to acrylate cements.
- PMMA bone cement was first used by Manchester orthopaedic surgeon, John Charnley, to fix an artificial hip joint into the bone of the femur and the pelvis. It has since been shown that PMMA bone cement is a highly effective way of securing the artificial prostheses into the living bone and joint replacement using this technique has become a commonplace and highly successful operative procedure.
- the paper discloses that the mechanism of aseptic loosening is initiated with debonding at the femoral stem-cement interface.
- the debonding becomes associated with the production of cracks within the cement mantle surrounding the prosthesis as the cement undergoes a fatigue fracture process.
- the gradual accumulation of this fatigue damage weakens the cement increasing its susceptibility to gross mechanical failure and also produces paniculate cement debris which stimulates an adverse biological response at the cement-bone interface further diminishing the integrity of the fixation.
- the outcome of this vicious circle of deterioration is a painful and unstable joint which demands the revision of the prosthesis.
- U.S. 4281420 AND 4365359 disclose the use of silane coupling agents for adhesion promotion of implant alloys in a process which comprises the application of a thin layer, 0.001 to 0.002 inches, of PMMA to the alloy surface either in the presence of a silane coupling agent or after application of silane coupling agent.
- the PMMA layer is annealed at 80°C to 170°C, generally at 160°C, cooled slowly, and the resulting prosthetic device is then ready for use and is fixed to bone with PMMA bone cement.
- the present invention provides alternative method for adhesion promotion of acrylate cement to implant alloys.
- a method of treating a medical implant having an exposed metallic, metal oxide or ceramic surface to enhance the adhering of acrylate cement thereto which comprises coating at least a portion of the exposed surface with a coupling agent consisting essentially of alkoxy silane having at least one polymerizable vinyl group.
- a coupling agent consisting essentially of alkoxy silane having at least one polymerizable vinyl group.
- coating refers to the deposition of a coating agent on the surface of the implant. It is understood that the coating may be continuous or discontinuous.
- a method of enhancing the adhesion of acrylate cement to a metallic surface which comprises treating the metallic surface with a coupling agent which is an alkoxy-silane having at least one addition-polymerisation group and applying to the treated surface the acrylate cement, in which the acrylate cement is not annealed.
- the invention also provides a metallic prosthetic element comprising a surface having an outer "layer" of an alkoxy silane having at least one addition- polymerisation group, the outer layer having been cured. This "layer" may be continuous or discontinuous.
- Each R 3 generally contains no more than 20 carbon atoms, preferably no more than 18.
- R 3 may optionally be substituted in available positions and/or interrupted by nitrogen, oxygen or sulphur atoms.
- the linking group X provides a chain of at least 4 atoms between the polymerizable moiety and the silane group.
- Preferred silanes are selected from:
- a general method of implanting a metallic surgical prosthesis in accordance with the invention comprises the steps of;
- the prosthesis is stored at ambient temperature for at least one day (i.e., about 24 hours), more preferably at least one week, prior to implantation to allow curing.
- the coating of step (a) should be carried out by contacting, particularly dipping the prosthesis in a dilute alcoholic solution of the silane.
- the coating may be uniform or applied pattern-wise.
- the concentration range should be 0.001 to 10%, w/v and the residence time 1 minute to 2 hours.
- a typical treatment comprises 10 minutes residence in a 1% w/v solution.
- the silane treatment may be carried out in the presence of ultrasound, e.g., in a conventional ultrasound cleaning bath, in order to promote interaction between the silane and the metal surface.
- ultrasound e.g., in a conventional ultrasound cleaning bath
- the prosthetic element is rinsed in clean solvent and dried and cured at elevated temperatures, preferably above 50°C.
- the final heat treatment to cure is typically 120°C for 15 minutes. The higher the temperature, generally the shorter the time required.
- the prosthesis is cleaned prior to step (a) by ultrasonic treatment in ethanol or similar cleaning solvents, e.g., for 1 minute to 2 hours, typically 10 minutes.
- ultrasonic treatment in ethanol or similar cleaning solvents, e.g., for 1 minute to 2 hours, typically 10 minutes.
- the invention will now be illustrated by the following Examples in which all experiments were performed with metal alloy lap-shear specimens treated in an identical manner to prepared metal implants. Samples were machined to flat oblong specimens (dimensions 51mm x 4mm) to enable lap-shear experiments to be performed.
- the following metal alloys were used: Ti alloy - (Ti6A14V)
- each sample Prior to treatment each sample was cleaned in ethanol for 10 minutes under ultrasonication. Once degreased, samples were rinsed in a clean solution of ethanol and dried at room temperature. At this stage same samples were surface treated with coupling agent. Treatment with coupling agent was performed in an ultrasonic bath using the required concentration of coupling agent in ethanol or methanol. After rinsing the treated sample in clean alcohol and drying at room temperature, samples were placed in an oven at 105-120°C for 15 minutes. Treated samples were then ready for application of PMMA cement. PMMA cement was applied in order to demonstrate the superior adhesion achieved by the present invention.
- the cement used was PMMA and activator with MMA monomer. Two samples were overlapped by 1cm and bonded together with the PMMA cement keeping the cement thickness between samples constant (approximately 0.5mm).
- Lap-shear specimens under test were fitted between the lower clamp and the moving cross-head of an Instron tester.
- the cross-head on the Instron (model 1026) was set to drive upwards at 5mm/min, using a 500kg load cell.
- Example 1 A series of Ti alloy samples were tested for interface shear strength; Three types of samples were employed. a) untreated sample (control) b) sample surface treated with a 1% solution of methacryloxypropyl trimethoxy silane. c) sample surface treated with a 1% solution of aminopropyltriethoxy silane.
- Example 2 The following types of sample were prepared using Ti alloy: (1) untreated control, (2) sample surface treated with 1% solution of methacryloxypropyl trimethoxy silane in accordance with the invention,
- Example 3 A series of experiments were conducted to prove the stability of the silane coating once applied to the prosthetic element.
- Ti alloy specimens were surface treated with 1% methacrylate silane as in Example 1 and placed in a desiccator, open to a normal laboratory environment, but with the lid in place to prevent the samples accumulating dust. Samples were
- Example 4 Lap-shear tests were conducted on different metal samples untreated and surface treated with methacryloxypropyl trimethoxysilane as in Example 1. The results are reported in the following Table.
- Silane (A) is designed with a longer organic chain between the silane end group and acrylate functionality, and Silane (B) contains three acrylate groups, rather than the single group present in MA used in the previous Examples.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Transplantation (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Materials For Medical Uses (AREA)
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP96912714A EP0820315A1 (en) | 1995-04-13 | 1996-04-12 | Adhesion promotion of orthopaedic implants |
JP8531815A JPH11503937A (en) | 1995-04-13 | 1996-04-12 | Methods for improving adhesion to orthopedic implants |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB9507910.9A GB9507910D0 (en) | 1995-04-13 | 1995-04-13 | Adhesion promotion of orthopaedic implants |
GB9507910.9 | 1995-04-13 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1996032970A1 true WO1996032970A1 (en) | 1996-10-24 |
Family
ID=10773174
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1996/005079 WO1996032970A1 (en) | 1995-04-13 | 1996-04-12 | Adhesion promotion of orthopaedic implants |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP0820315A1 (en) |
JP (1) | JPH11503937A (en) |
GB (1) | GB9507910D0 (en) |
WO (1) | WO1996032970A1 (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1156053A2 (en) * | 2000-05-18 | 2001-11-21 | National Starch and Chemical Investment Holding Corporation | Adhesion promoters which are silanes comprising carbamate- or urea-groups, and a group with donor or acceptor functionality |
WO2003025077A2 (en) * | 2001-09-19 | 2003-03-27 | Coripharm Gmbh & Co | Bone coupling agent, layered adhesive system and method for producing the same |
KR100642970B1 (en) * | 1998-06-11 | 2006-11-13 | 존슨 앤드 존슨 비젼 케어, 인코포레이티드 | Biomedical devices with hydrophilic coatings |
US20110065824A1 (en) * | 2009-09-15 | 2011-03-17 | Fujifilm Corporation | Curable composition for imprints |
US10011617B2 (en) | 2014-09-26 | 2018-07-03 | The Chemours Company Fc, Llc | Isocyanate derived organosilanes |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6276266B2 (en) | 2012-08-08 | 2018-02-07 | スリーエム イノベイティブ プロパティズ カンパニー | Photovoltaic device with encapsulated barrier film |
KR20150041058A (en) | 2012-08-08 | 2015-04-15 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | Diurethane (meth)acrylate-silane compositions and articles including the same |
JP6296877B2 (en) * | 2014-03-31 | 2018-03-20 | 株式会社松風 | Novel sulfur-containing silane coupling agent and dental composition containing the same |
JP6220723B2 (en) * | 2014-03-31 | 2017-10-25 | 株式会社松風 | Novel silane coupling agent and dental composition containing the same |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3919773A (en) * | 1973-12-20 | 1975-11-18 | Sybron Corp | Direct moldable implant material |
EP0017937A2 (en) * | 1979-04-11 | 1980-10-29 | Kanebo, Ltd. | Bonding compositions to the hard tissue of human body |
US4365359A (en) * | 1979-02-15 | 1982-12-28 | Raab S | PMMA Coated bone connective prostheses and method of forming same |
DE4416857C1 (en) * | 1994-05-13 | 1995-06-29 | Fraunhofer Ges Forschung | Hydrolysable and polymerisable silane(s) useful in coating, adhesive and moulding compsns. or composites |
-
1995
- 1995-04-13 GB GBGB9507910.9A patent/GB9507910D0/en active Pending
-
1996
- 1996-04-12 JP JP8531815A patent/JPH11503937A/en active Pending
- 1996-04-12 EP EP96912714A patent/EP0820315A1/en not_active Withdrawn
- 1996-04-12 WO PCT/US1996/005079 patent/WO1996032970A1/en not_active Application Discontinuation
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3919773A (en) * | 1973-12-20 | 1975-11-18 | Sybron Corp | Direct moldable implant material |
US4365359A (en) * | 1979-02-15 | 1982-12-28 | Raab S | PMMA Coated bone connective prostheses and method of forming same |
EP0017937A2 (en) * | 1979-04-11 | 1980-10-29 | Kanebo, Ltd. | Bonding compositions to the hard tissue of human body |
DE4416857C1 (en) * | 1994-05-13 | 1995-06-29 | Fraunhofer Ges Forschung | Hydrolysable and polymerisable silane(s) useful in coating, adhesive and moulding compsns. or composites |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100642970B1 (en) * | 1998-06-11 | 2006-11-13 | 존슨 앤드 존슨 비젼 케어, 인코포레이티드 | Biomedical devices with hydrophilic coatings |
EP1156053A2 (en) * | 2000-05-18 | 2001-11-21 | National Starch and Chemical Investment Holding Corporation | Adhesion promoters which are silanes comprising carbamate- or urea-groups, and a group with donor or acceptor functionality |
EP1156053A3 (en) * | 2000-05-18 | 2003-08-27 | National Starch and Chemical Investment Holding Corporation | Adhesion promoters which are silanes comprising carbamate- or urea-groups, and a group with donor or acceptor functionality |
KR100700121B1 (en) * | 2000-05-18 | 2007-03-28 | 내쇼날 스타치 앤드 케미칼 인베스트멘트 홀딩 코포레이션 | Adhesion promoters containing silane, carbamate or urea, and donor or acceptor functionality |
WO2003025077A2 (en) * | 2001-09-19 | 2003-03-27 | Coripharm Gmbh & Co | Bone coupling agent, layered adhesive system and method for producing the same |
WO2003025077A3 (en) * | 2001-09-19 | 2003-08-28 | Coripharm Gmbh & Co | Bone coupling agent, layered adhesive system and method for producing the same |
US20110065824A1 (en) * | 2009-09-15 | 2011-03-17 | Fujifilm Corporation | Curable composition for imprints |
US10011617B2 (en) | 2014-09-26 | 2018-07-03 | The Chemours Company Fc, Llc | Isocyanate derived organosilanes |
Also Published As
Publication number | Publication date |
---|---|
EP0820315A1 (en) | 1998-01-28 |
JPH11503937A (en) | 1999-04-06 |
GB9507910D0 (en) | 1995-05-31 |
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