A photosensitive cyclodextrin polymer and its nanoparticles

A cyclodextrin polymer and nanoparticle technology is applied in the field of functional polymer materials to achieve good photosensitivity

Inactive Publication Date: 2015-10-21
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, studies on photosensitive CD polymers and their assemblies have not been reported

Method used

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  • A photosensitive cyclodextrin polymer and its nanoparticles
  • A photosensitive cyclodextrin polymer and its nanoparticles
  • A photosensitive cyclodextrin polymer and its nanoparticles

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Embodiment 1, sulfonylated β-cyclodextrin (6-OTs-β-CD)

[0014] Add 50g (44mmol) of β-CD to 1L of water dissolved with 16g (400mmol) of NaOH, stir vigorously in an ice bath at 0°C, and slowly add 36g (187mmol) of p-toluenesulfonyl chloride (TsCl) to the system, resulting in a white Precipitation, reaction at 0 ° C for 2h. The insoluble matter was removed by suction filtration, and the pH of the filtrate was adjusted to 7.0 with 10% HCl by volume. The precipitate was recrystallized with deionized water and dried in vacuo to obtain monosulfonylated β-CD (6-OTs-β-CD).

Embodiment 2

[0015] Example 2, thiolated β-cyclodextrin (6-SH-β-CD)

[0016] Add 12g (9.3mmol) 6-OTs-β-CD and 12g (158mmol) thiourea into 480mL anhydrous DMF, and react at 75°C for 48h. After the reaction, cool to room temperature. Then add 1.4L of anhydrous ether and stir, the precipitate is filtered, and washed twice with acetone. The resulting product and 480mg Na 2 S 2 o 5 Dissolve in 400ml of 1mol / L NaOH and stir at room temperature for 30min. Acidify with 1mol / L HCl to pH = 3, then add 20mL trichlorethylene, and sonicate for 10min. The precipitate is filtered, recrystallized twice with water, and dried to obtain 6-SH-β-CD, which is a white powder.

Embodiment 3

[0017] Embodiment 3, poly 3,4-dihydroxycinnamic acid (PDHCA)

[0018] Add 43g (239mmol) of DHCA and 4g (48.8mmol) of sodium acetate into 100mL of acetic anhydride, pass through N2, react at 140°C for 1h, and at 200°C for 6h. The obtained product was washed twice with ethanol and deionized water twice, and dried at 50° C., and the obtained product was a brown powder.

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Abstract

The invention discloses a photosensitive cyclodextrin polymer and nanoparticles thereof, which belong to the field of functional polymer materials. According to the photosensitive cyclodextrin polymer and the nanoparticles thereof, a natural plant monomer 3,4-dihydroxy cinnamic acid (caffeic acid, DHCA) is used as a raw material, a homopolymer PDHCA (poly(3,4-dihydroxy cinnamic acid)) of the DHCA is prepared by a gradual condensation polymerization method; a Michael addition reaction is carried out on the homopolymer and thiolated beta-cyclodextrin (6-SH-beta-CD) to prepare a photosensitive graft polymer (PDHCA-g-CD) with CD as a pendant group; the cyclodextrin polymers are self-assembled into nanoparticles under certain conditions and are crosslinked and immobilized by ultraviolet light; the grafting rate, the particle size and the ultraviolet light crosslinking degree of CD are controlled by adjusting the feeding ratio. The polymer and the nanoparticles thereof disclosed by the invention have excellent adsorption inclusion property, biocompatibility and biodegradability and can be applied in such fields as drug slow release systems, tissue engineering, environmental protection, etc.

Description

technical field [0001] The invention discloses a photosensitive cyclodextrin polymer and its nano particles, belonging to the field of functional polymer materials. Background technique [0002] Cyclodextrin (CD for short) is a general term for a series of cyclic oligosaccharides produced by amylose under the action of cyclodextrin glucosyltransferase produced by Bacillus, usually containing 6-8 D(+) -Glucopyranose units, each glucose unit is combined with 1,4-glycosidic bonds to form a ring, referred to as α-, β- and γ-CD respectively. The CD molecule has a slightly conical hollow cylindrical three-dimensional ring structure. In its structure, the outer side is composed of secondary hydroxyl groups of C2 and C3 and primary hydroxyl groups of C6, which is hydrophilic; The shielding effect forms the hydrophobic region. Its internal cavity is hydrophobic and its external surface is hydrophilic, so that it can form clathrates and molecular assembly systems with many organic a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G81/02C08F120/04C08G63/91C08G63/688C08G63/06C08B37/16
Inventor 施冬健刘蓉瑾叶瑾陈明清段芳倪忠斌
Owner JIANGNAN UNIV
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