CA2226131C - Preparation of polymeric materials having cell poliferation-promoting properties - Google Patents
Preparation of polymeric materials having cell poliferation-promoting properties Download PDFInfo
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- CA2226131C CA2226131C CA002226131A CA2226131A CA2226131C CA 2226131 C CA2226131 C CA 2226131C CA 002226131 A CA002226131 A CA 002226131A CA 2226131 A CA2226131 A CA 2226131A CA 2226131 C CA2226131 C CA 2226131C
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- 239000000463 material Substances 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title description 8
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- 239000000178 monomer Substances 0.000 claims abstract description 42
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- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims abstract description 30
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 32
- -1 alkali metal salt Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 13
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 12
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 8
- 239000011248 coating agent Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
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- 239000000919 ceramic Substances 0.000 claims description 4
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- 125000000542 sulfonic acid group Chemical group 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 229920002614 Polyether block amide Polymers 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
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- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- VWVRASTUFJRTHW-UHFFFAOYSA-N 2-[3-(azetidin-3-yloxy)-4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound O=C(CN1C=C(C(OC2CNC2)=N1)C1=CN=C(NC2CC3=C(C2)C=CC=C3)N=C1)N1CCC2=C(C1)N=NN2 VWVRASTUFJRTHW-UHFFFAOYSA-N 0.000 description 1
- ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
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- 239000002253 acid Substances 0.000 description 1
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- 229940072049 amyl acetate Drugs 0.000 description 1
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- 229940093499 ethyl acetate Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
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- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 125000005385 peroxodisulfate group Chemical group 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F246/00—Copolymers in which the nature of only the monomers in minority is defined
-
- 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
- A61L27/28—Materials for coating prostheses
- A61L27/34—Macromolecular 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
- A61L33/00—Antithrombogenic treatment of surgical articles, e.g. sutures, catheters, prostheses, or of articles for the manipulation or conditioning of blood; Materials for such treatment
- A61L33/06—Use of macromolecular materials
- A61L33/064—Use of macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F228/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Transplantation (AREA)
- Dermatology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Hematology (AREA)
- Surgery (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Medical Uses (AREA)
- Apparatus Associated With Microorganisms And Enzymes (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
- Prostheses (AREA)
- Paints Or Removers (AREA)
- Polymerisation Methods In General (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19700078A DE19700078A1 (de) | 1997-01-03 | 1997-01-03 | Herstellung von polymeren Materialien mit zellproliferationsbegünstigenden Eigenschaften |
| DE19700078.9 | 1997-01-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2226131A1 CA2226131A1 (en) | 1998-07-03 |
| CA2226131C true CA2226131C (en) | 2006-09-19 |
Family
ID=7816789
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002226131A Expired - Fee Related CA2226131C (en) | 1997-01-03 | 1998-01-02 | Preparation of polymeric materials having cell poliferation-promoting properties |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US6365692B1 (enExample) |
| EP (1) | EP0852237B1 (enExample) |
| JP (1) | JPH10195143A (enExample) |
| AT (1) | ATE219502T1 (enExample) |
| CA (1) | CA2226131C (enExample) |
| DE (2) | DE19700078A1 (enExample) |
| DK (1) | DK0852237T3 (enExample) |
| NO (1) | NO315706B1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19908318A1 (de) * | 1999-02-26 | 2000-08-31 | Michael Hoffmann | Hämokompatible Oberflächen und Verfahren zu deren Herstellung |
| US7056868B2 (en) * | 2001-07-30 | 2006-06-06 | Cabot Corporation | Hydrophobe associative polymers and compositions and methods employing them |
| FR2850107B1 (fr) * | 2003-01-17 | 2007-03-30 | L A R S Laboratoire D Applic E | Procede de traitement de surfaces polymeres |
| US20040208983A1 (en) * | 2003-04-16 | 2004-10-21 | Hill Gregory A. | Antimicrobial coatings for ophthalmic devices |
| US7968650B2 (en) | 2006-10-31 | 2011-06-28 | Johnson & Johnson Vision Care, Inc. | Polymeric compositions comprising at least one volume excluding polymer |
| WO2012092566A1 (en) * | 2010-12-30 | 2012-07-05 | Surmodics, Inc. | Cell attachment coatings and methods |
| US9631190B2 (en) | 2012-06-29 | 2017-04-25 | Surmodics, Inc. | Cell attachment coatings and methods using phosphorous-containing photoreagent |
| FR3013584B1 (fr) | 2013-11-22 | 2015-11-20 | L A R S Laboratoire D Applic Et De Rech Scient | Ligament prothetique biomimetique resorbable |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4056517A (en) * | 1971-12-28 | 1977-11-01 | Hoechst Aktiengesellschaft | Modacryl filaments and fibers and process for their manufacture |
| JPS5846242B2 (ja) * | 1980-07-30 | 1983-10-15 | 東ソー株式会社 | 重合体エマルションの製造方法 |
| HU187669B (en) * | 1982-03-31 | 1986-02-28 | Richter Gedeon Vegyeszet | Process for producing new copolymeres and salts |
| JPS6136309A (ja) * | 1984-07-30 | 1986-02-21 | Nippon Shokubai Kagaku Kogyo Co Ltd | 耐塩，耐光性吸水剤 |
| AU605217B2 (en) | 1987-05-12 | 1991-01-10 | Ecolab Inc. | Disinfectant polymeric coatings for hard surfaces |
| EP0290642B1 (de) * | 1987-05-12 | 1993-11-03 | Mittermayer, Christian, Dr. med. | Verfahren zur Besiedlung einer Polymeroberfläche mit menschlichen Gefässinnenhautzellen |
| JPH03501978A (ja) * | 1988-08-22 | 1991-05-09 | コモンウェルス・サイエンティフィック・アンド・インダストリアル・リサーチ・オーガニゼイション | 細胞の付着および増殖のための材料 |
| US5278200A (en) * | 1992-10-30 | 1994-01-11 | Medtronic, Inc. | Thromboresistant material and articles |
| TW228529B (enExample) * | 1992-12-23 | 1994-08-21 | Ciba Geigy | |
| US5783502A (en) * | 1995-06-07 | 1998-07-21 | Bsi Corporation | Virus inactivating coatings |
| US5756625A (en) * | 1996-10-11 | 1998-05-26 | Minnesota Mining And Manufacturing Company | Stabilized adhesive microspheres |
-
1997
- 1997-01-03 DE DE19700078A patent/DE19700078A1/de not_active Withdrawn
- 1997-11-19 DK DK97120234T patent/DK0852237T3/da active
- 1997-11-19 AT AT97120234T patent/ATE219502T1/de not_active IP Right Cessation
- 1997-11-19 EP EP97120234A patent/EP0852237B1/de not_active Expired - Lifetime
- 1997-11-19 DE DE59707555T patent/DE59707555D1/de not_active Expired - Fee Related
- 1997-12-26 JP JP9359951A patent/JPH10195143A/ja not_active Ceased
- 1997-12-30 US US09/001,143 patent/US6365692B1/en not_active Expired - Fee Related
- 1997-12-30 NO NO19976153A patent/NO315706B1/no not_active IP Right Cessation
-
1998
- 1998-01-02 CA CA002226131A patent/CA2226131C/en not_active Expired - Fee Related
-
2001
- 2001-11-15 US US09/999,295 patent/US6417000B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE19700078A1 (de) | 1998-07-09 |
| ATE219502T1 (de) | 2002-07-15 |
| NO315706B1 (no) | 2003-10-13 |
| NO976153L (no) | 1998-07-06 |
| DK0852237T3 (da) | 2002-10-14 |
| US6417000B1 (en) | 2002-07-09 |
| CA2226131A1 (en) | 1998-07-03 |
| EP0852237A2 (de) | 1998-07-08 |
| EP0852237A3 (de) | 1998-09-16 |
| JPH10195143A (ja) | 1998-07-28 |
| NO976153D0 (no) | 1997-12-30 |
| US6365692B1 (en) | 2002-04-02 |
| DE59707555D1 (de) | 2002-07-25 |
| EP0852237B1 (de) | 2002-06-19 |
| US20020068804A1 (en) | 2002-06-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |