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Surface modification of polymers via surface active and reactive end groups

a technology of reactive end group and surface modification, which is applied in the direction of synthetic polymeric active ingredients, drug compositions, extracellular fluid disorder, etc., can solve the problems of difficult removal of organic solvent after removal, uncontrolled degradation process, and significant ablation tendency of base polymers

Inactive Publication Date: 2011-12-01
DSM IP ASSETS BV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0010]The present invention overcomes the aforementioned shortcomings by providing a method that can be applied to modify the polymeric surface without the shortcomings of the aforementioned wet chemical or physical irradiation pre-treatment of the surface to afford reactive bonding sites.

Problems solved by technology

The method lacks the chemical interaction of pre-formed substrate with the formed polymer and requires the use of organic solvent to facilitate diffusion of the monomers to the substrate and therefore poses the difficulty of removing the organic solvent afterwards.
This “grafting-from” method calls for a separate step of surface preparation and may not applicable to many radical inert polymer substrates.
The excitation with plasma is very surface specific, however, in addition to the requirement of vacuum, the ablation tendency of the base polymer may be significant.
Also, the contribution of the high-energy deep-UV radiation during a direct plasma exposure may lead to an uncontrolled degradation process.
In addition, the delicate topological feature of the surface may be damaged due to the exposure to the irradiation.
These “grafting-to” surface treatments involve harsh condition which may adversely affect the bulk properties and surface morphology.
However, there has been limited success due to the limited availability of reactive functional groups on the surface directly accessible to a surface modifier.

Method used

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  • Surface modification of polymers via surface active and reactive end groups
  • Surface modification of polymers via surface active and reactive end groups
  • Surface modification of polymers via surface active and reactive end groups

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0067]Using surface active and reactive diamine as an end capping agent, a polyurethane with amine terminated end groups can be prepared by a two-step method: I) First, isocyanate terminated polyurethane was prepared in DMAc solution from diisocyanate such as MDI, polyol such as PTMO, PEO, and polyol such as polycarbonate diol, silicone diol, and chain extender such as butane diol, ethylene diamine, ethanol amine, and other short chain diamine, diol, and amino alcohol. The stoichiometric ratio of NCO / H was kept more than 1 so that the polyurethane chain ends were terminated with isocyanate groups, II) Excess amount of surface active and reactive diamine was then added to the reaction mixture to allow the covalent attachment of these end groups at one site, leaving the other amine group for subsequent surface modification. The polymer thus prepared can be used as a coating or can be precipitated and dried for thermal processing such as extrusion, molding. Because of the surface activ...

example 2

[0070]Polyurethane with 10-undecen-1-ol end groups was first prepared. Tubing was extruded from the resin having the surface enriched with the vinyl end groups which were then reacted with an epoxy silane coupling agent to form a surface abundant with epoxide, the epoxide functional surface can serve as platform for immobilization of hydrophilic molecules such as PVP, PEO, PVA, PMA, polyelectrolytes, and other biomolecules bearing functional group reactive to epoxide to afford wet lubricity. Applying multifunctional hydrophilic molecules may also lock-in the surface with desired properties. Reaction may also take place with underlying reactive end groups due to the penetration / diffusion of surface modifying agents, these underlying end groups will serve as the reservoir for replenishing the surface in demand. Alternatively, the epoxy groups can react with polyamine to form an amine rich surface which can serve as platform for immobilization of biomolecules such as commercially avail...

example 3

[0073]Hydroxyl-functional surface active and reactive end groups capping agents can also be optimized and incorporated in polyurethanes as surface active and reactive end group. Examples of such compounds are 11-(9-decenyldimethylsilyl)undecan-1-ol and 11-(triallylsilyl)undecan-1-ol and 11-(triallylsilyl)undecan-1-ol. The synthesis of the molecules is described below:

Synthesis of 11-(9-decenyldimethylsilyl)undecan-1-ol

[0074]The title compound was synthesized as illustrated in FIG. 5. 10-undecen-1-ol (85 g, 0.5 mol) and p-toluenesulfonic acid monohydrate (0.38 g, 2 mmol) were dissolved in dichloromethane (150 mL) and cooled in ice / water bath under nitrogen. To this solution was then added 3,4-dihydro-2H-pyran (50.4 g, 0.6 mol) dropwise over an hour. After the addition, the solution was stirred for additional two hours in ice / water bath and turned into purple. The solution was then diluted with hexanes (300 mL), washed with aqueous sodium bicarbonate (150 mL×2), and dried over MgSO4. ...

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Abstract

Polymer surface modification method comprising the steps of first forming a surface of primary reactive end groups tethered to the polymer chain ends during fabrication of an article, and then modifying the reactive surface with bio-active molecules, hydrophilic and hydrophobic monomers, oligomers, or polymers to attain specific surface properties. Alternatively, a multifunctional coupling agent can be used to couple the primary reactive group to a second reactive group capable of reacting with a functional group associated with bio-active molecules, hydrophilic and hydrophobic monomers, oligomers, and polymers to attain specific surface properties. The invention involves bringing reactive endgroups to the surface with surface active spacer attached to the polymer chain end. The surface active spacer allows the migration and enrichment of reactive end groups to the surface during fabrication. The invention provides medical devices having a bio-interface with anti-thrombogenic properties, lubricity, selective adsorption, and antimicrobial properties.

Description

FIELD OF THE INVENTION[0001]This invention provides methods for modifying the surface properties of polymeric articles, by first forming a surface of reactive end groups tethered to the polymer chain ends during fabrication of an article, and subsequently reacting the reactive end group surface with bio-active molecules, hydrophilic and hydrophobic monomers, oligomers or polymers to attain specific surface properties. In an embodiment of the invention, a multifunctional coupling agent can be used to couple the primary reactive group to a second reactive group capable of reacting with a functional group associated with bio-active molecules, hydrophilic and hydrophobic monomers, oligomers and polymers to attain specific surface properties. This method of the invention involves bringing reactive end groups to the surface of the polymeric article with surface active spacers attached to the reactive end groups. The surface active spacers promote the migration and enrichment of reactive e...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K49/00B29C45/00A61P31/00A61P7/02C08G18/83A61K31/785
CPCC08J7/12C08G18/837C08G18/08C08J7/14A61P31/00A61P7/02A61K2800/61
Inventor WANG, SHANGERWARD, ROBERT S.TIAN, YUANJIANG, XUWEIMCCREA, KEITHCURTIN, SCOTT
Owner DSM IP ASSETS BV
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