DE69731752T2 - Kombinatorisches verfahren zur herstellung von kaskadenpolymeroberflächen - Google Patents
Kombinatorisches verfahren zur herstellung von kaskadenpolymeroberflächen Download PDFInfo
- Publication number
- DE69731752T2 DE69731752T2 DE69731752T DE69731752T DE69731752T2 DE 69731752 T2 DE69731752 T2 DE 69731752T2 DE 69731752 T DE69731752 T DE 69731752T DE 69731752 T DE69731752 T DE 69731752T DE 69731752 T2 DE69731752 T2 DE 69731752T2
- Authority
- DE
- Germany
- Prior art keywords
- monomers
- substrate
- functionalities
- layer
- mixture
- 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.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 27
- 229920000642 polymer Polymers 0.000 title claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000000178 monomer Substances 0.000 claims abstract description 57
- 239000000758 substrate Substances 0.000 claims abstract description 48
- 239000000203 mixture Substances 0.000 claims abstract description 40
- 239000012948 isocyanate Substances 0.000 claims abstract description 23
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 23
- 239000010410 layer Substances 0.000 claims abstract description 16
- 239000002344 surface layer Substances 0.000 claims abstract description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 230000000295 complement effect Effects 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 5
- 125000005592 polycycloalkyl group Polymers 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 238000010511 deprotection reaction Methods 0.000 claims 2
- 239000000412 dendrimer Substances 0.000 description 13
- 229920000736 dendritic polymer Polymers 0.000 description 13
- 239000000463 material Substances 0.000 description 9
- 238000010276 construction Methods 0.000 description 8
- 238000000576 coating method Methods 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012216 screening Methods 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 239000000693 micelle Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 238000012804 iterative process Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000011253 protective coating Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 0 CCN(C)*(CCCCCC(C)=O)(CCC*C=[N+](C)[O-])CCC*C(C)=O Chemical compound CCN(C)*(CCCCCC(C)=O)(CCC*C=[N+](C)[O-])CCC*C(C)=O 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 229920000333 poly(propyleneimine) Polymers 0.000 description 1
- 229920005554 polynitrile Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- -1 polysiloxanes Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C40—COMBINATORIAL TECHNOLOGY
- C40B—COMBINATORIAL CHEMISTRY; LIBRARIES, e.g. CHEMICAL LIBRARIES
- C40B40/00—Libraries per se, e.g. arrays, mixtures
- C40B40/04—Libraries containing only organic compounds
- C40B40/14—Libraries containing macromolecular compounds and not covered by groups C40B40/06 - C40B40/12
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/71—Monoisocyanates or monoisothiocyanates
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/71—Monoisocyanates or monoisothiocyanates
- C08G18/718—Monoisocyanates or monoisothiocyanates containing silicon
-
- 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
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/002—Dendritic macromolecules
- C08G83/003—Dendrimers
-
- C—CHEMISTRY; METALLURGY
- C40—COMBINATORIAL TECHNOLOGY
- C40B—COMBINATORIAL CHEMISTRY; LIBRARIES, e.g. CHEMICAL LIBRARIES
- C40B50/00—Methods of creating libraries, e.g. combinatorial synthesis
- C40B50/08—Liquid phase synthesis, i.e. wherein all library building blocks are in liquid phase or in solution during library creation; Particular methods of cleavage from the liquid support
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/11—Compounds covalently bound to a solid support
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S977/00—Nanotechnology
- Y10S977/70—Nanostructure
- Y10S977/754—Dendrimer, i.e. serially branching or "tree-like" structure
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Structural Engineering (AREA)
- Engineering & Computer Science (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Polymerisation Methods In General (AREA)
- Medicinal Preparation (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US705905 | 1996-08-28 | ||
| US08/705,905 US5886126A (en) | 1996-08-28 | 1996-08-28 | Combinatorial method of forming cascade polymer surfaces |
| PCT/US1997/014914 WO1998008885A1 (en) | 1996-08-28 | 1997-08-25 | Combinatorial method of forming cascade polymer surfaces |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69731752D1 DE69731752D1 (de) | 2004-12-30 |
| DE69731752T2 true DE69731752T2 (de) | 2005-12-22 |
Family
ID=24835434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69731752T Expired - Fee Related DE69731752T2 (de) | 1996-08-28 | 1997-08-25 | Kombinatorisches verfahren zur herstellung von kaskadenpolymeroberflächen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5886126A (enExample) |
| EP (1) | EP0922062B1 (enExample) |
| JP (2) | JP2000516985A (enExample) |
| AT (1) | ATE283301T1 (enExample) |
| AU (1) | AU4235497A (enExample) |
| CA (1) | CA2264035C (enExample) |
| DE (1) | DE69731752T2 (enExample) |
| WO (1) | WO1998008885A1 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3866809B2 (ja) * | 1996-12-19 | 2007-01-10 | 松下電器産業株式会社 | 有機膜及びその製造方法 |
| US7250534B1 (en) | 1999-07-27 | 2007-07-31 | University Of South Florida | Performance of energy storage devices: potential areas for dendritic chemistry involvement |
| US7448258B2 (en) * | 1999-10-29 | 2008-11-11 | Avery Dennison Corporation | High throughput screening for moisture barrier characteristics of materials |
| EP1326892A2 (en) | 2000-10-12 | 2003-07-16 | University of Rochester | Compositions that inhibit proliferation of cancer cells |
| US20020146684A1 (en) * | 2001-04-09 | 2002-10-10 | Meldal Morten Peter | One dimensional unichemo protection (UCP) in organic synthesis |
| DE10158149A1 (de) * | 2001-11-28 | 2003-06-18 | Bayer Ag | Silangruppen enthaltende Polymere |
| WO2003065997A2 (en) | 2002-02-06 | 2003-08-14 | Vicor Technologies, Inc. | Anti-infarction molecules |
| AU2003253580A1 (en) * | 2002-02-26 | 2003-11-17 | University Of Minnesota | Variants of nedd4l associated with hypertension and viral budding |
| EP1575992A4 (en) | 2002-08-05 | 2007-02-21 | Univ Rochester | CHEMICAL PROTEINS FROM PROTEIN TRANSDUCATING DOMAIN / DEAMINASE, RELATED COMPOUNDS AND THEIR USES |
| US20050106068A1 (en) * | 2003-11-18 | 2005-05-19 | Abdul Malik | Sol-gel dendron separation and extraction capillary column |
| US8076090B2 (en) | 2005-04-05 | 2011-12-13 | Corning Incorporated | Label free biosensors and cells |
| AU2005332058B2 (en) | 2005-05-19 | 2011-12-01 | The Government Of The United States Of America, As Represented By The Secretary, Department Of Health And Human Services, Centers For Disease Control And Prevention | Functional epitopes of Streptococcus pneumoniae PsaA antigen and uses thereof |
| EP2392645A1 (en) | 2005-10-14 | 2011-12-07 | MUSC Foundation For Research Development | Targeting PAX2 for the induction of DEFB1-mediated tumor immunity and cancer therapy |
| US8080534B2 (en) * | 2005-10-14 | 2011-12-20 | Phigenix, Inc | Targeting PAX2 for the treatment of breast cancer |
| ES2625109T3 (es) * | 2005-10-25 | 2017-07-18 | Starpharma Pty Limited | Compuestos macromoleculares que tienen estequiometría controlada |
| EP2560001B1 (en) | 2006-09-21 | 2016-04-13 | University of Rochester | Compositions and methods related to protein displacement therapy for myotonic distrophy |
| US8999317B2 (en) | 2006-11-01 | 2015-04-07 | University Of Rochester | Methods and compositions related to the structure and function of APOBEC3G |
| WO2008098182A1 (en) | 2007-02-08 | 2008-08-14 | University Of Utah Research Foundation | Methods and compositions related to inhibition of viral entry |
| WO2010019963A2 (en) * | 2008-08-15 | 2010-02-18 | Georgetown University | Na channels, disease, and related assays and compositions |
| US20120070443A1 (en) | 2008-12-02 | 2012-03-22 | University Of Utah Research Foundation | Pde1 as a target therapeutic in heart disease |
| WO2011022502A1 (en) | 2009-08-18 | 2011-02-24 | Georgetown University | Boronic acid compositions and methods related to cancer |
| JP2013507365A (ja) | 2009-10-07 | 2013-03-04 | サンフォード−バーナム メディカル リサーチ インスティテュート | 血餅結合脂質化合物に関する方法および組成物 |
| CA2784145A1 (en) | 2009-12-18 | 2011-06-23 | Sanford-Burnham Medical Research Institute | Methods and compositions related to clot-binding compounds |
| CA2868735C (en) | 2011-03-28 | 2020-02-25 | University Of Utah Research Foundation | D-peptide conjugates comprising a membrane localizing potency-enhancing cargo molecule for inhibiting hiv entry |
| US12025615B2 (en) | 2017-09-15 | 2024-07-02 | Arizona Board Of Regents On Behalf Of Arizona State University | Methods of classifying response to immunotherapy for cancer |
| WO2021067550A1 (en) | 2019-10-02 | 2021-04-08 | Arizona Board Of Regents On Behalf Of Arizona State University | Methods and compositions for identifying neoantigens for use in treating and preventing cancer |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5610268A (en) * | 1992-01-13 | 1997-03-11 | Dsm N.V. | Dendritic macromolecule and the preparation thereof |
| US5414075A (en) * | 1992-11-06 | 1995-05-09 | Bsi Corporation | Restrained multifunctional reagent for surface modification |
-
1996
- 1996-08-28 US US08/705,905 patent/US5886126A/en not_active Expired - Lifetime
-
1997
- 1997-08-25 CA CA002264035A patent/CA2264035C/en not_active Expired - Fee Related
- 1997-08-25 WO PCT/US1997/014914 patent/WO1998008885A1/en not_active Ceased
- 1997-08-25 EP EP97940611A patent/EP0922062B1/en not_active Expired - Lifetime
- 1997-08-25 AU AU42354/97A patent/AU4235497A/en not_active Abandoned
- 1997-08-25 JP JP10511785A patent/JP2000516985A/ja active Pending
- 1997-08-25 DE DE69731752T patent/DE69731752T2/de not_active Expired - Fee Related
- 1997-08-25 AT AT97940611T patent/ATE283301T1/de not_active IP Right Cessation
-
2006
- 2006-03-17 JP JP2006075728A patent/JP2006188717A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP0922062B1 (en) | 2004-11-24 |
| JP2006188717A (ja) | 2006-07-20 |
| EP0922062A1 (en) | 1999-06-16 |
| ATE283301T1 (de) | 2004-12-15 |
| CA2264035C (en) | 2007-10-23 |
| DE69731752D1 (de) | 2004-12-30 |
| WO1998008885A1 (en) | 1998-03-05 |
| CA2264035A1 (en) | 1998-03-05 |
| EP0922062A4 (en) | 1999-11-10 |
| JP2000516985A (ja) | 2000-12-19 |
| AU4235497A (en) | 1998-03-19 |
| US5886126A (en) | 1999-03-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |