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Polymeric substrates with fluoroalkoxycarbonyl groups for amine capture

A fluoroalkyl, polymer material technology

Inactive Publication Date: 2012-06-06
3M INNOVATIVE PROPERTIES CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This competing reaction can lead to incomplete or ineffective immobilization of amino-containing materials on the substrate
[0007] Although the azlactone functional group is more stable to hydrolysis, it is difficult to synthesize azlactones bonded to any polymerizable group other than vinyl

Method used

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  • Polymeric substrates with fluoroalkoxycarbonyl groups for amine capture
  • Polymeric substrates with fluoroalkoxycarbonyl groups for amine capture
  • Polymeric substrates with fluoroalkoxycarbonyl groups for amine capture

Examples

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example

[0141] These examples are illustrative only, and are not intended to limit the scope of the appended claims. All parts, percentages, ratios, etc. in the examples, as well as in the remainder of the specification, are by weight unless otherwise indicated. Solvents and other reagents used were obtained from Sigma-Aldrich Chemical Company, Milwaukee, Wisconsin unless otherwise indicated.

[0142] Acronym

[0143] initials or business name

preparation example 1

[0144] Preparation Example 1: Preparation of Oxyethyl Glutaryl Chloride Monomethacrylate

[0145] A solution of 2-hydroxyethyl methacrylate (57.0 g), glutaric anhydride (50.0 g) and phenothiazine (0.15 g) in dry THF (250 mL) was cooled in a glass reaction vessel with an ice / water bath . Triethylamine (46.0 g in 10 mL THF) was added dropwise to the stirred mixture. The mixture was allowed to warm to room temperature and stirred for 2 days. The solution was concentrated using a rotary evaporator and the remaining mixture was dissolved in CH 2 Cl 2 (250 ml). This solution was washed twice with 150 ml of 5% hydrochloric acid solution and twice with 100 ml of water. After washing, the solution was washed with MgSO 4 Dry, and remove the solvent with a rotary evaporator to yield 105.4 g of oxyethyl glutarate monomethacrylate as a pink liquid. A sample of this oxyethyl glutarate monomethacrylate (50.0 g) was dissolved in CH 2 Cl 2 (100ml). To this was added phenothiazine (...

preparation example 2

[0146] Preparation Example 2: Preparation of Hexafluoroisopropyl Ester of Glutaryl Chloride Monooxyethyl Methacrylate prepare

[0147] Hexafluoroisopropanol (8.6 g), CH 2 Cl 2(50 mL), and ethyldiisopropylamine (5.4 g) were slowly added to the stirred mixture of acid chloride from Preparative Example 1 (10.5 g) over several minutes. The resulting mixture was stirred for 2 hours and the volatiles were removed with a rotary evaporator. The residue was dissolved in methyl tert-butyl ether and filtered through a microfilter. Solvent was removed using a rotary evaporator to give 9.0 grams of oil. The oil was dissolved in hexane (20 mL) and filtered through a microfilter. The solvent was removed using a rotary evaporator to give 8.5 g of a clear beige liquid. The identity of the product was confirmed by proton and fluorine nuclear magnetic resonance (NMR).

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Abstract

Amino-containing materials can be attached to polymeric materials having a pendant amine capture group that includes a fluoroalkoxycarbonyl group. An amino-containing material can react with the pendant amine capture group by a nucleophilic substitution reaction. The product of the reaction is an alcohol and a pendant group that contains a carbonylimino group. The reaction results in the connection of the amino-containing material to the polymeric material. The polymeric materials are often disposed on a surface of a substrate and the connection of the amino-containing material to the polymeric material results in the immobilization of the amino-containing material on the substrate.

Description

[0001] priority statement [0002] This patent application claims priority to U.S. Provisional Patent Application Serial No. 60 / 871,294, filed December 21, 2006, and U.S. Serial No. 11 / 856,144, filed September 17, 2007, the disclosures of which are incorporated by reference Incorporated into this article. technical field [0003] Methods of attaching an amino-containing material to a polymeric material and securing the amino-containing material to a substrate are described. Background technique [0004] Amino-containing materials, such as amino-containing analytes, amino acids, DNA, RNA, proteins, cells, tissues, organelles, immunoglobulins, or fragments thereof, immobilized on the surface of a substrate can be used in numerous applications. For example, immobilized biological amino-containing materials can be used for medical diagnosis of diseases or genetic defects, for bioseparation or for detection of different biomolecules. Immobilization of amino-containing material...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F8/32
CPCC08F8/32Y10T436/25Y10T436/173845C08F20/00C08F20/22
Inventor 乔治·G·I·摩尔查尔斯·M·利尔拉胡尔·R·沙阿
Owner 3M INNOVATIVE PROPERTIES CO