Preparation method of biomimetic mussel adhesive based on synthesis of oxetane derivatives

A technology for oxetane and derivatives is applied in the field of preparation of biomimetic mussel glue, can solve the problems of biomimetic mussel glue biocompatibility, high adhesion strength and difficult to achieve unification, etc., and achieves a simple and efficient synthesis method and biological High compatibility and the effect of breaking through technical bottlenecks

Inactive Publication Date: 2013-09-11
QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The purpose of the present invention is to provide a new preparation method of bionic mussel glue with high strength and certain biocompatibility, to solve the biocompatibility (especially in vivo) and high viscosity of existing bionic mussel glue. Difficult to achieve unification in terms of attached strength

Method used

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  • Preparation method of biomimetic mussel adhesive based on synthesis of oxetane derivatives
  • Preparation method of biomimetic mussel adhesive based on synthesis of oxetane derivatives
  • Preparation method of biomimetic mussel adhesive based on synthesis of oxetane derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033]

[0034] Add oxetane monomer to the 50ml reaction bottle MO (3.9g 0.03mol), CMO (0.25g 0.93mmol) and dichloromethane (5mL), through argon for 30min, add BF with a syringe 3 ﹒ Et 2 O (19uL), react at 0°C for 6 hours under the protection of argon, add absolute ethanol (2mL) to terminate the reaction, drop the concentrated reaction solution into absolute ethanol (100mL) under stirring, and dissolve the precipitate repeatedly Precipitated three times and dried to obtain the copolymer I m (3.3g) (M n =25KDa M w / M n =1.7).

[0035] Add the prepared copolymer in the 50ml reaction bottle I m , tetrahydrofuran (6mL), boron tribromide (0.7g 2.8mmol), and react under the protection of argon for 10 hours. The concentrated reaction solution was dropped into n-hexane (50mL) under stirring, and the precipitate was dissolved and precipitated three times, and dried to obtain the polymer Ⅱm (2.8g). polymer Ⅱm Dissolve in 5mL of absolute ethanol, add 0.05g of ferric c...

Embodiment 2

[0038]

[0039] Add oxetane monomer to the 50ml reaction bottle MO (3.9g 0.03mol), HCBO (4.0g 0.0075mol) and dichloromethane (10mL), through argon for 30min, add BF with a syringe 3 ﹒ Et 2 O (19uL), react at 0°C for 6 hours under the protection of argon, add absolute ethanol (2mL) to terminate the reaction, drop the concentrated reaction solution into absolute ethanol (100mL) under stirring, and dissolve the precipitate repeatedly Precipitated three times and dried to obtain the copolymer I HB (6.3g) (M n =24KDa M w / M n =1.9).

[0040] Add the prepared copolymer in the 50ml reaction bottle I HB , tetrahydrofuran (15mL), concentrated hydrochloric acid (2mL), and reacted for 10 hours under the protection of argon. The concentrated reaction solution was dropped into n-hexane (50mL) under stirring, and the precipitate was dissolved and precipitated three times, and dried to obtain the polymer II HB (5.1g). polymer II HB Dissolve in 8mL of absolute ethanol, a...

Embodiment 3

[0043]

[0044] Add oxetane monomer to the 50ml reaction bottle HO (5.58g 0.03mol), MHCBO (3.92g 0.0075mol) and dichloromethane (10mL), through argon for 30min, add BF with a syringe 3 ﹒ Et 2 O (19uL), react at 0°C for 6 hours under the protection of argon, add absolute ethanol (2mL) to terminate the reaction, drop the concentrated reaction solution into absolute ethanol (100mL) under stirring, and dissolve the precipitate repeatedly Precipitated three times and dried to obtain the copolymer I HBM (7.6g) (M n =20KDa M w / M n =2.0 ).

[0045] Add the prepared copolymer in the 50ml reaction bottle I HBM , tetrahydrofuran (15mL), concentrated hydrochloric acid (2mL), and reacted for 10 hours under the protection of argon. The concentrated reaction solution was dropped into n-hexane (50mL) under stirring, and the precipitate was dissolved and precipitated three times, and dried to obtain the polymer II HBM (5.9g). polymer II HBM Dissolve in 8mL of absolute...

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Abstract

The invention relates to a preparation method of a biomimetic mussel adhesive based on the synthesis of oxetane derivatives. The preparation method comprises the following main steps: preparing a phenolic hydroxy protected polymer with a catechol side-chain structure through ring-opening copolymerization of two oxetane derivative monomers; carrying out deprotection on the polymer so as to obtain a catechol structure containing polymer; and after the catechol structure containing polymer is dissolved, adding a certain amount of a crosslinking agent into the polymer, and uniformly mixing so as to obtain the biomimetic mussel adhesive. The method has the characteristics that: 1) the synthesis method is simple and efficient, and raw materials and reagents used in the process of reaction are cheap and easily available, thereby facilitating the amplification of an operating process and industrial production; and 2) the bonding strength is over 5 MPa, so that an effect that a synthetic polymer simulates the attachment protein properties of natural mussels is successfully achieved, and a purpose of integrating certain biocompatibility and high adhesion strength is reached; therefore, the method provides is a novel synthesis technique of biomimetic mussel adhesives and provides a new way for developing novel bionic polymer materials based on the effective protein components of shellfish.

Description

[0001] technical field [0002] The invention relates to a method for preparing bionic mussel glue, in particular to a method for preparing bionic mussel glue with higher strength and better biocompatibility by using oxetane derivatives. [0003] Background technique [0004] Mussels have a strong adhesive ability, and the adhesive proteins secreted by them can adhere to almost all substrate materials, even including polytetrafluoroethylene, and this natural adhesion does not exist in the underwater or wet environment of synthetic adhesives. Defects with poor performance, and will not cause human immune response, so it has a wide range of applications in waterproof sealants and adhesives in the field of national defense and marine engineering, and medical adhesives for bonding soft and hard tissues in the field of biomedicine. The application prospect has attracted much attention. [0005] The study found that there is a large amount of 3, 4-dihydroxyphenylalanine (DOPA) i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/32C08G65/22C08J3/24C09J171/02
Inventor 万晓波贾明辰穆有炳
Owner QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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