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Alkoxy silicane functionalized betaine zwitterionic compound and preparation method and application thereof

A technology of alkoxysilane function and alkoxysilane function, which is applied in the field of betaine-type zwitterionic compounds and their preparation, can solve the problems of limited types of zwitterionic compounds, achieve improved protein adsorption resistance, and improve biocompatibility Excellent performance and antifouling ability

Inactive Publication Date: 2013-08-21
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the current product range of zwitterionic compounds is very limited
Zwitterionic compounds designed and prepared especially for the application requirements of biological materials and material surface modification have not been reported yet.

Method used

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  • Alkoxy silicane functionalized betaine zwitterionic compound and preparation method and application thereof
  • Alkoxy silicane functionalized betaine zwitterionic compound and preparation method and application thereof
  • Alkoxy silicane functionalized betaine zwitterionic compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Under nitrogen protection, put 212.5 grams (1.0mol) of chloromethyltriethoxysilane, 10l.0 grams (1.0mol) of triethylamine, and 100 grams of toluene in a reflux device, thermometer, and dropping funnel. In the four-necked flask, start a strong stirrer at a speed of 150 rpm, dropwise add 102.0 g (1.0 mol) of 3-dimethylaminopropylamine within 20 minutes, raise the temperature to 120°C, and reflux for 6 hours; The system was cooled down to room temperature, the product was suction filtered to remove the amine salt precipitate, and the filtrate was purified by vacuum distillation to obtain the corresponding intermediate 3-dimethylaminopropylaminomethyltriethoxysilane.

[0038] Dissolve 1.0 mol of the intermediate 3-dimethylaminopropylaminomethyltriethoxysilane in 100 grams of toluene, and add 1,3-propane sultone dropwise at room temperature. The total amount added is 1.0 mol. The addition time was 30 minutes; after the dropwise addition was completed, the reaction was refluxed...

Embodiment 2

[0041] Under the protection of nitrogen, put 255.0 grams (1.2mol) of chloromethyltriethoxysilane, 10l.0 grams (1.0mol) of triethylamine, and 100 grams of toluene in a container with a reflux device, a thermometer and a dropping funnel. In the four-necked flask, start a strong stirrer at a speed of 150 rpm, dropwise add 102.0 g (1.0 mol) of 3-dimethylaminopropylamine within 20 minutes, raise the temperature to 100°C, and reflux for 7 hours; The system was cooled down to room temperature, the product was suction filtered to remove the amine salt precipitate, and the filtrate was purified by vacuum distillation to obtain the corresponding intermediate 3-dimethylaminopropylaminomethyltriethoxysilane.

[0042] Dissolve 1.0 mol of the intermediate 3-dimethylaminopropylaminomethyltriethoxysilane in 100 grams of toluene, add γ-butyrolactone dropwise at room temperature, the total dropping amount is 1.0 mol, and the dropping time is 40 Minutes; after the dropwise addition, reflux react...

Embodiment 3

[0045] Under nitrogen protection, put 182.7 grams (1.0mol) of γ-chloropropylmethyldimethoxysilane, 151.5 grams (1.5mol) of triethylamine, and 100 grams of toluene in a dropping funnel with a reflux device and a thermometer. In a four-neck flask, start a strong stirrer at a speed of 150 rpm, add 102.0 grams (1.0 mol) of 3-dimethylaminopropylamine dropwise within 20 minutes, raise the temperature to 120 ° C, and reflux for 6 hours; The reaction system was lowered to room temperature, the product was suction filtered to remove the amine salt precipitate, and the filtrate was purified by vacuum distillation to obtain the corresponding intermediate 3-dimethylaminopropylaminopropylmethyldimethoxysilane.

[0046] Dissolve 1.0 mol of the intermediate 3-dimethylaminopropylaminopropylmethyldimethoxysilane in 100 grams of toluene, and add 1,3-propane sultone dropwise at room temperature, with a total dropwise amount of 1.0 mol , the dropwise addition time is 30 minutes; after the dropwis...

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Abstract

The invention discloses an alkoxy silane functionalized betaine zwitterionic compound and a preparation method thereof. A structural formula of the compound is shown as a formula (i), and the compound has the characteristics of both a zwitterionic compound and a silane coupling agent. The preparation method comprises the following steps of: reacting chlorine-containing alkoxy silane, tertiary amine-containing diamine compounds and triethylamine with heating under the protection of nitrogen to obtain a tertiary amine-containing silane intermediate; and reacting sultone or alkyl lactone with the tertiary amine-containing silane intermediate under the anhydrous condition to obtain the alkoxy silane functionalized betaine zwitterionic compound. Hydrolysable groups of which the structure is similar to that of the silane coupling agent in molecules of the compound are connected with the surface of a material by a covalent bond, so that the compound can be fixed on the surface of the selected material perpetually; and the method for modifying the surface of the material by using the compound has the advantages that: the process is simple, the cost is low, and the method is suitable for large-scale production, and the compound has obvious superiority on the surface treatment of large-scale parts and equipment.

Description

technical field [0001] The present invention relates to novel zwitterionic compounds, in particular to a novel alkoxysilane-functionalized betaine-type zwitterionic compound capable of modifying or modifying the surface or interface of different materials and a preparation method thereof. Background technique [0002] The adsorption of proteins on the surface of materials is a very common phenomenon, which has attracted close attention from academia and industry. In many cases, protein adsorption can cause many undesired results. For example, cell adsorption and proliferation caused by non-specific adsorption of proteins on biomedical materials such as biosensors; thrombus or infection caused by artificial materials; biofouling blockage of separation and purification membranes of biological products; adhesion of fouling organisms on marine ships, increasing navigational resistance Wait. At the molecular level, these problems all have one clear commonality: proteins rapidly...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/18C08L83/06C08K13/02C08K5/544C08K5/548C08K3/26C08K3/36
Inventor 刘云鸿李光吉尹以高
Owner SOUTH CHINA UNIV OF TECH
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