Micro-nano material, product of covalent modification of hydrophilic substances for surface of micro-nano material, and preparation method

A covalent modification, micro-nano technology, applied in the preparation of organic compounds, carbamic acid derivatives, sulfonic acid, etc., can solve the problems of reducing reactivity and modification degree

Active Publication Date: 2017-03-22
CHONGQING FARSIGHTED BLUE DRAGON FBD BIOTECH CO LTD CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In order to ensure that the re-modification step after each layer of modification reaction has a sufficiently high degree of modification, there must be enough carboxyl groups in the modifier used in each modification reaction, but the electrostatic repulsion between these carboxyl groups will reduce the interaction between the modifier itself and the surface of the micro-nano material. Reactivity and degree of modification of reactive esters

Method used

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  • Micro-nano material, product of covalent modification of hydrophilic substances for surface of micro-nano material, and preparation method
  • Micro-nano material, product of covalent modification of hydrophilic substances for surface of micro-nano material, and preparation method
  • Micro-nano material, product of covalent modification of hydrophilic substances for surface of micro-nano material, and preparation method

Examples

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preparation example Construction

[0093] The invention also discloses a method for preparing the product of covalently modifying the surface of the micro-nano material with a hydrophilic substance, comprising the following steps:

[0094] a. Generate carboxyl active ester on the surface of the micro-nano material, that is, use the micro-nano material with carboxyl or / and potential carboxyl on the surface as the micro-nano material to be modified, and convert the carboxyl or / and potential carboxyl on its surface into an active ester; The micro-nano material refers to an organic polymer with a size of at least one dimension not exceeding 100 μm, a composite of an organic polymer and an organic or inorganic micro-nano material, and has two shapes; one is a particle and the particle size is less than 100 μm , which can be spherical and approximately spherical; the other is a thin film with a thickness of less than 100 μm but does not limit the area size of this thin film, including free thin films or thin films att...

Embodiment 1

[0202] Example 1. Preparation of Representative Type A1-1 Modifiers

[0203] 1-1. Synthesis of N,N-dimethylglycine active ester: in tetrahydrofuran (THF), saturated dimethylglycine (DMG) plus NHS and DCC (the molar ratio of the three is 1:1:1), and the reaction was stirred overnight at room temperature; The precipitate was filtered off, the supernatant was concentrated 20 times under reduced pressure, and ether was added to precipitate the precipitate; then dissolved in the minimum amount of hot THF, and ether was added to precipitate the precipitate. In N, N-dimethylglycine active ester (DMG-CO-NHS).

[0204] 1-2. Pentaethylene hexamine bis-Boc protected primary amine synthesis: pentaethylene hexamine is saturated dissolved in dimethylformamide (DMF), and double the molar amount of bis-tert-butyl pyrocarbonate (Boc-O-Boc ), stirred and reacted at room temperature for 60 minutes; added diethyl ether to precipitate a precipitate; redissolved in the minimum amount of DMF, added...

Embodiment 2

[0207] Example 2. Preparation of Representative Type A2-3 Modifiers

[0208] 2-1. Synthesis of active esters of N-Boc protected amino acids: straight-chain amino acids with amino groups within 6 carbons at the end (glycine, 3-aminopropionic acid, 4-aminobutyric acid, 5-aminopentanoic acid, 6-aminocaproic acid) 1) Saturated and dissolved in water at room temperature, adding twice the molar amount of bis-tert-butanol pyrocarbonate (Boc-O-Boc) saturated and dissolved in THF, stirring at room temperature for 2.0 hours; adding isopropanol until a large amount of precipitates precipitated; Re-dissolve to the minimum amount of DMF, add ether to precipitate the precipitate; repeat twice to obtain N-Boc protected amino acid. Finally, saturate the N-Boc protected amino acid dissolved in DMF, add DCC and NHS (molar ratio 1:1:1); stir at room temperature overnight. Filter off the precipitate, add ether to the supernatant to precipitate the precipitate; redissolve in the least amount of h...

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Abstract

The invention discloses a micro-nano material, a product of covalent modification of hydrophilic substances for the surface of the micro-nano material, and a preparation method. Carboxyl groups or potential carboxyl groups are contained on the surface of the micro-nano material and transformed into active esters; the product of covalent modification of the hydrophilic substances for the surface is obtained through taking a hydrophilic compound or / and a hydrophilic polymer containing aliphatic primary amines or / and aliphatic secondary amines as a modifier, forming amido bonds from the active esters for the surface and the hydrophilic compound or / and the hydrophilic polymer, and carrying out covalent modification; during preparation, enough carboxyl groups or potential carboxyl groups are generated on the surface of a polymeric material from monomers containing carboxyl groups or / and potential carboxyl groups and transformed into active esters, then amido bonds are formed from the active esters and a modifier with aliphatic primary amines and / or aliphatic secondary amines, potential facultative ionic groups and hydrophilic connection arms, and having a moderate volume, and covalent modification layers are obtained; and multilayer covalent modification is realized during a process of repeatedly generating the active esters on the surface of the product of covalent modification and then forming the amido bonds from the active esters and the hydrophilic modifier, and the surface of the micro-nano material is efficiently covered with the hydrophilic modifier having a medium volume, thus the non-specific adsorption of the modification product for biological molecules is remarkably reduced.

Description

technical field [0001] The invention relates to a micro-nano material, a product covalently modified with a hydrophilic substance on the surface and a preparation method; the essence belongs to biomedical micro-nano material and its surface modification technology. Background technique [0002] In the present invention, substances with a molecular weight of less than 500 Daltons are called compounds, and substances with a molecular weight of not less than 500 Daltons are called polymers. [0003] Modification of the surface of micro-nano materials with hydrophilic compounds / polymers can reduce their non-specific adsorption and enhance applications, such as polyethylene glycol (PEG), zwitterionic substances, hydrophilic natural biopolymers (heparin and albumin) etc.) to modify. Natural biopolymers are prone to non-specific adsorption on other biomolecules, and still have strong non-specific adsorption on hydrophobic small molecules. On the contrary, PEG and zwitterionic com...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F290/06C08F220/58C08F222/38C08F8/32C08F8/34C08G65/332C08G65/333C08G81/02C07C269/04C07C269/06C07C271/20C07C231/12C07C237/08C07C303/02C07C309/14
CPCC07C231/12C07C269/04C07C269/06C07C303/02C07D207/404C08F8/32C08F8/34C08F290/062C08G65/3328C08G65/33306C08G81/025C08F220/58C07C271/20C07C237/08C07C309/14
Inventor 廖飞龙高波杨海冯虎
Owner CHONGQING FARSIGHTED BLUE DRAGON FBD BIOTECH CO LTD CHINA
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