AU2003273331A1 - Compounds containing quaternary carbons and silicon containing groups, medical devices, and methods. - Google Patents
Compounds containing quaternary carbons and silicon containing groups, medical devices, and methods. Download PDFInfo
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- AU2003273331A1 AU2003273331A1 AU2003273331A AU2003273331A AU2003273331A1 AU 2003273331 A1 AU2003273331 A1 AU 2003273331A1 AU 2003273331 A AU2003273331 A AU 2003273331A AU 2003273331 A AU2003273331 A AU 2003273331A AU 2003273331 A1 AU2003273331 A1 AU 2003273331A1
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 title claims abstract description 14
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title abstract description 23
- 229910052710 silicon Inorganic materials 0.000 title abstract description 22
- 239000010703 silicon Substances 0.000 title abstract description 22
- 229920002635 polyurethane Polymers 0.000 claims abstract description 42
- 239000004814 polyurethane Substances 0.000 claims abstract description 42
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 12
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229920000642 polymer Polymers 0.000 claims description 133
- 125000003118 aryl group Chemical group 0.000 claims description 82
- 125000001931 aliphatic group Chemical group 0.000 claims description 62
- 229920006395 saturated elastomer Polymers 0.000 claims description 60
- 125000005842 heteroatom Chemical group 0.000 claims description 58
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 239000003054 catalyst Substances 0.000 claims description 23
- 125000002947 alkylene group Chemical group 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 229910003849 O-Si Inorganic materials 0.000 claims description 15
- 229910003872 O—Si Inorganic materials 0.000 claims description 15
- 239000012620 biological material Substances 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
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- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 5
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- -1 for example Chemical group 0.000 description 37
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- 125000000962 organic group Chemical group 0.000 description 21
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- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 8
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
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- 239000005056 polyisocyanate Substances 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
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- 150000001721 carbon Chemical group 0.000 description 6
- UCXUKTLCVSGCNR-UHFFFAOYSA-N diethylsilane Chemical compound CC[SiH2]CC UCXUKTLCVSGCNR-UHFFFAOYSA-N 0.000 description 6
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- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 5
- 238000002835 absorbance Methods 0.000 description 5
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 5
- 229910000077 silane Inorganic materials 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- 235000013877 carbamide Nutrition 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- 238000005649 metathesis reaction Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 238000002390 rotary evaporation Methods 0.000 description 4
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 description 3
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- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
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- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 3
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 229920003225 polyurethane elastomer Polymers 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
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- LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
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- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- YHFTXQZVDRPFNY-UHFFFAOYSA-N 6,6-dimethylundeca-1,10-diene Chemical compound C=CCCCC(C)(C)CCCC=C YHFTXQZVDRPFNY-UHFFFAOYSA-N 0.000 description 2
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- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- CZEPJJXZASVXQF-ZETCQYMHSA-N ethyl (2s)-2,6-diaminohexanoate Chemical compound CCOC(=O)[C@@H](N)CCCCN CZEPJJXZASVXQF-ZETCQYMHSA-N 0.000 description 1
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- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 210000003709 heart valve Anatomy 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
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- 238000002347 injection Methods 0.000 description 1
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- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- WABPQHHGFIMREM-UHFFFAOYSA-N lead(0) Chemical compound [Pb] WABPQHHGFIMREM-UHFFFAOYSA-N 0.000 description 1
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
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- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
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- 238000005191 phase separation Methods 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
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- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
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- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
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- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
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- 239000004945 silicone rubber Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
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- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
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- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61N—ELECTROTHERAPY; MAGNETOTHERAPY; RADIATION THERAPY; ULTRASOUND THERAPY
- A61N1/00—Electrotherapy; Circuits therefor
- A61N1/02—Details
- A61N1/04—Electrodes
- A61N1/05—Electrodes for implantation or insertion into the body, e.g. heart electrode
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/61—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6204—Polymers of olefins
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Radiology & Medical Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Polyurethanes Or Polyureas (AREA)
- Materials For Medical Uses (AREA)
- Prostheses (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41172502P | 2002-09-17 | 2002-09-17 | |
| US60/411,725 | 2002-09-17 | ||
| US49078003P | 2003-07-29 | 2003-07-29 | |
| US60/490,780 | 2003-07-29 | ||
| PCT/US2003/029153 WO2004026936A1 (en) | 2002-09-17 | 2003-09-16 | Compounds containing quaternary carbons and silicon-containing groups, medical devices, and methods. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2003273331A1 true AU2003273331A1 (en) | 2004-04-08 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2003273331A Abandoned AU2003273331A1 (en) | 2002-09-17 | 2003-09-16 | Compounds containing quaternary carbons and silicon containing groups, medical devices, and methods. |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20040054210A1 (enExample) |
| EP (1) | EP1539850B1 (enExample) |
| JP (1) | JP2005538799A (enExample) |
| AT (1) | ATE406397T1 (enExample) |
| AU (1) | AU2003273331A1 (enExample) |
| CA (1) | CA2499347A1 (enExample) |
| DE (1) | DE60323243D1 (enExample) |
| WO (1) | WO2004026936A1 (enExample) |
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| US7101956B2 (en) * | 2001-11-14 | 2006-09-05 | Medtronic, Inc. | Compounds containing quaternary carbons, medical devices, and methods |
| WO2004026933A1 (en) * | 2002-09-17 | 2004-04-01 | Medtronic, Inc. | Polymers with soft segments containing silane-containing groups, medical devices, and methods |
| US6984700B2 (en) * | 2002-09-17 | 2006-01-10 | Medtronic, Inc. | Compounds containing silicon-containing groups, medical devices, and methods |
| WO2006057582A1 (en) * | 2004-11-24 | 2006-06-01 | St. Jude Medical Ab | Attachment of tubing in a cardiac lead |
| DE102006031866A1 (de) * | 2006-07-10 | 2008-01-17 | Webasto Ag | Brennstoffzellensystem und Verfahren zum Beeinflussen des Wärmehaushaltes eines Brennstoffzellensystems |
| US20090326077A1 (en) * | 2008-06-27 | 2009-12-31 | Cardiac Pacemakers, Inc. | Polyisobutylene urethane, urea and urethane/urea copolymers and medical devices containing the same |
| US9574043B2 (en) * | 2009-01-12 | 2017-02-21 | University Of Massachusetts Lowell | Polyisobutylene-based polyurethanes |
| EP2467174B1 (en) | 2009-08-21 | 2018-09-26 | Cardiac Pacemakers, Inc. | Crosslinkable polyisobutylene-based polymers and medical devices containing the same |
| US8374704B2 (en) | 2009-09-02 | 2013-02-12 | Cardiac Pacemakers, Inc. | Polyisobutylene urethane, urea and urethane/urea copolymers and medical leads containing the same |
| US8644952B2 (en) * | 2009-09-02 | 2014-02-04 | Cardiac Pacemakers, Inc. | Medical devices including polyisobutylene based polymers and derivatives thereof |
| WO2012087480A1 (en) | 2010-12-20 | 2012-06-28 | Cardiac Pacemakers, Inc. | Lead having a conductive polymer conductor |
| JP2015535538A (ja) | 2012-11-21 | 2015-12-14 | ユニバーシティー オブ マサチューセッツＵｎｉｖｅｒｓｉｔｙ ｏｆ Ｍａｓｓａｃｈｕｓｅｔｔｓ | 高強度ポリイソブチレンポリウレタン |
| US10526429B2 (en) | 2017-03-07 | 2020-01-07 | Cardiac Pacemakers, Inc. | Hydroboration/oxidation of allyl-terminated polyisobutylene |
| CN110997746B (zh) | 2017-08-17 | 2021-12-28 | 心脏起搏器股份公司 | 用于增强的耐久性的光交联聚合物 |
| EP3740253B1 (en) | 2018-01-17 | 2023-08-16 | Cardiac Pacemakers, Inc. | End-capped polyisobutylene polyurethane |
Family Cites Families (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3948829A (en) * | 1973-04-05 | 1976-04-06 | Hitco | Strippable, thin, protective coating |
| US4208506A (en) * | 1977-07-25 | 1980-06-17 | Bausch & Lomb Incorporated | Polyparaffinsiloxane shaped article for use in biomedical applications |
| US4316973A (en) * | 1979-09-10 | 1982-02-23 | The University Of Akron | Novel telechelic polymers and processes for the preparation thereof |
| US4276394A (en) * | 1979-09-10 | 1981-06-30 | The University Of Akron | Novel telechelic polymers, block copolymers and processes for the preparation thereof |
| US4568732A (en) * | 1985-01-09 | 1986-02-04 | The University Of Akron | Continuous telechelic polymer process |
| AT385040B (de) * | 1985-03-15 | 1988-02-10 | Lim Kunststoff Tech Gmbh | Verfahren zur herstellung von polyurethanen, insbesondere von polyurethanelastomeren, sowie verfahren zur radikalischen polymerisation |
| US4647643A (en) * | 1985-11-08 | 1987-03-03 | Becton, Dickinson And Company | Soft non-blocking polyurethanes |
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-
2003
- 2003-09-16 EP EP03755831A patent/EP1539850B1/en not_active Expired - Lifetime
- 2003-09-16 CA CA002499347A patent/CA2499347A1/en not_active Abandoned
- 2003-09-16 JP JP2004537881A patent/JP2005538799A/ja active Pending
- 2003-09-16 US US10/663,926 patent/US20040054210A1/en not_active Abandoned
- 2003-09-16 DE DE60323243T patent/DE60323243D1/de not_active Expired - Lifetime
- 2003-09-16 AU AU2003273331A patent/AU2003273331A1/en not_active Abandoned
- 2003-09-16 WO PCT/US2003/029153 patent/WO2004026936A1/en not_active Ceased
- 2003-09-16 AT AT03755831T patent/ATE406397T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005538799A (ja) | 2005-12-22 |
| WO2004026936A1 (en) | 2004-04-01 |
| US20040054210A1 (en) | 2004-03-18 |
| CA2499347A1 (en) | 2004-04-01 |
| DE60323243D1 (de) | 2008-10-09 |
| ATE406397T1 (de) | 2008-09-15 |
| EP1539850B1 (en) | 2008-08-27 |
| EP1539850A1 (en) | 2005-06-15 |
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| MK5 | Application lapsed section 142(2)(e) - patent request and compl. specification not accepted |