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Cellulose 6-aminocaproate and its synthesis method and application

A technology of aminocaproic acid and cellulose ester, applied in coating and other directions, can solve the problems of high viscosity of solution, inconvenient experimental operation, unsatisfactory effect of inhibiting non-specific adsorption of proteins, etc., and achieves low cost, wide source, inhibition of non-specific The effect of adsorption

Inactive Publication Date: 2016-08-17
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] A technical problem to be solved by the present invention is that according to the existing microfluidic chip surface modifying agent, the solution viscosity in the dynamic physical coating is large, which brings inconvenience to the experimental operation, and is not effective in inhibiting the non-specific adsorption of proteins. Ideal shortcoming, provide a new compound that can be used as a surface modifier for microfluidic chips - 6-aminocaproic acid cellulose ester, and provide a synthetic method for the surface modifier

Method used

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  • Cellulose 6-aminocaproate and its synthesis method and application
  • Cellulose 6-aminocaproate and its synthesis method and application
  • Cellulose 6-aminocaproate and its synthesis method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0029] 1. Synthesis of N-tert-butoxycarbonyl-6-aminocaproic acid

[0030] Add 1.60 (40 mmol) sodium hydroxide, 2.62 g (20 mmol) 6-aminocaproic acid, 4.37 g (20 mmol) di-tert-butyl dicarbonate, 10 mL distilled water, 10 mL 1,4- Dioxane, stirred at -10°C for 10 hours, after the reaction, slowly pour the reaction solution into a 100mL beaker, acidify the reaction solution with aqueous hydrochloric acid solution with a concentration of 2mmol / L to pH 2, and use ethyl acetate Repeated extraction of the resulting product 3 times, collecting the ethyl acetate extract, drying the ethyl acetate extract with anhydrous sodium sulfate, then evaporating and concentrating the ethyl acetate extract, adding petroleum ether to the concentrated extract for recrystallization, filtering, About 4.3 g of N-tert-butoxycarbonyl-6-aminocaproic acid was obtained as a white crystalline solid.

[0031] 2. N,N'-carbonyldiimidazole activates N-tert-butoxycarbonyl-6-aminocaproic acid

[0032] Add 4.27 g (1...

Embodiment 2

[0039]In the synthesis of N-tert-butoxycarbonyl-6-aminocaproic acid cellulose ester step 3 in Example 1, the fiber is taken according to the molar ratio of cellulose and N-tert-butoxycarbonyl-6-aminocaproic acid as 1:4 Element, dissolving cellulose and tetrabutylammonium fluoride trihydrate in dimethyl sulfoxide in a mass ratio of 1:6, reacting at room temperature under nitrogen protection for 15 minutes, pouring into the reaction solution obtained in step 2, and Under the protection of nitrogen, react at 50°C for 25 hours, precipitate the precipitate with ultrapure water, filter, and wash the precipitate with ethanol to obtain N-tert-butoxycarbonyl-6-aminocaproic acid cellulose. The other steps were the same as in Example 1 to obtain cellulose 6-aminocaproate, and the total average degree of substitution (DS) was calculated to be 0.72.

Embodiment 3

[0041] In the synthesis of N-tert-butoxycarbonyl-6-aminocaproic acid cellulose ester step 3 in Example 1, take the fiber according to the molar ratio of cellulose and N-tert-butoxycarbonyl-6-aminocaproic acid as 1:5 Element, dissolving cellulose and tetrabutylammonium fluoride trihydrate in dimethyl sulfoxide in a mass ratio of 1:6, reacting at room temperature under nitrogen protection for 15 minutes, pouring into the reaction solution obtained in step 2, and Under the protection of nitrogen, react at 90°C for 18 hours, precipitate the precipitate with ultrapure water, filter, and wash the precipitate with ethanol to obtain N-tert-butoxycarbonyl-6-aminocaproic acid cellulose ester. The other steps were the same as in Example 1 to obtain cellulose 6-aminocaproate, the total average degree of substitution (DS) of which was calculated to be 0.93.

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Abstract

The invention discloses 6-amino caproic acid cellulose ester as well as a synthetic method and application thereof. According to the 6-amino caproic acid cellulose ester, some hydroxyls of cellulose are substituted by a group as shown in the specification, and the total average degree of substitution of the group on each glucose unit ring is 0.6-1.2. The 6-amino caproic acid cellulose ester is synthesized from raw materials derived from a wealth of sources, the reaction conditions are gentle, the cost is low, the synthesized 6-amino caproic acid cellulose ester can be used as a surface modifying reagent for a polydimethylsiloxane micro-fluidic chip and physically adsorbed on the surface of a passage of the polydimethylsiloxane micro-fluidic chip to form a monomolecular film with positive charges, so that the surface hydrophilicity of the passage of the polydimethylsiloxane micro-fluidic chip can be improved, and nonspecific adsorption of protein on the surface of the passage of the micro-fluidic chip can be effectively inhibited, so high-efficiency reappearance and separation of analyte are realized.

Description

technical field [0001] The invention belongs to the technical field of microfluidic chip surface modification reagents, and specifically relates to cellulose 6-aminocaproate and its synthesis method and application. Background technique [0002] Cellulose esters are derivatives prepared from cellulose as an intermediate, and cellulose is a compound composed of hundreds or thousands of anhydroglucose units. This combination of anhydroglucose units is called poly-β-glucoside chains, and cellulose esters can be prepared by esterifying cellulose with specific carboxylic acids or anhydrides. The cellulose esters that are actually commercially used include: cellulose acetate, cellulose nitrate, cellulose acetate butyrate and cellulose sulfonate. These cellulose esters are widely used in industrial production. However, in today's most promising microfluidic analysis systems, the application of cellulose esters is greatly limited. [0003] The dynamic physical coating method is cu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B3/14C08J7/04
Inventor 党福全刘超
Owner SHAANXI NORMAL UNIV
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