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CN-116425946-B - Polyurethane material based on curcumin and preparation method and application thereof

CN116425946BCN 116425946 BCN116425946 BCN 116425946BCN-116425946-B

Abstract

The invention belongs to the technical field of high polymer materials, and discloses a polyurethane material based on curcumin, and a preparation method and application thereof. The polyurethane material based on curcumin is prepared from a curcumin chain extender and polyether amine modified curcumin. The curcumin chain extender and the polyether amine modified curcumin adopted by the invention both contain natural antibacterial and anti-inflammatory components curcumin, and the curcumin is taken as a main component for synthesizing the polyurethane material, so that the content of the antibacterial and anti-inflammatory components in the polyurethane material can be obviously improved, the curcumin content in the polyurethane material can reach about 30 percent, the transparency and mechanical properties of the material are not affected, and simultaneously, imine bonds in the polyether amine modified curcumin are reversible dynamic covalent bonds, and the slow release of the curcumin can be effectively controlled through the permeation of water molecules and the slow hydrolysis of the imine dynamic bonds.

Inventors

  • HOU HONGHAO
  • GAN YANCHANG

Assignees

  • 南方医科大学

Dates

Publication Date
20260505
Application Date
20230425

Claims (9)

  1. 1. The polyurethane material based on the curcumin is characterized in that the raw materials for preparing the polyurethane material based on the curcumin comprise a curcumin chain extender and polyether amine modified curcumin; The curcumin chain extender has a structural general formula shown in the following formula (1): (1); wherein R is the residue of a compound having one or more hydroxyl groups at the terminal or side chain; the structural general formula of the polyether amine modified curcumin is shown as the following formula (2): (2); Wherein n 1 is an integer from 1 to 50 and R 0 is H or a-CH 3 group.
  2. 2. The curcumin-based polyurethane material according to claim 1, wherein the curcumin chain extender is selected from one or more of the following compounds: 、 、 、 、 、 、 。
  3. 3. the curcumin-based polyurethane material according to claim 1, wherein the polyetheramine-modified curcumin is selected from one or more of the following compounds: 、 、 、 、 。
  4. 4. a process for the preparation of a curcumin based polyurethane material as claimed in any one of claims 1-3, characterized by comprising the steps of: Dissolving the curcumin chain extender in a polar solvent, mixing with dihydric alcohol, diisocyanate and HDI trimer, and reacting to obtain a curcumin polyurethane prepolymer; and mixing the polyether amine modified curcumin and the curcumin polyurethane prepolymer, and reacting to obtain the curcumin-based polyurethane material.
  5. 5. The method of claim 4, wherein the method of preparing the curcumin chain extender comprises the steps of: dissolving curcumin in a polar solvent, mixing with a compound with one or more hydroxyl groups at the tail end or side chains and an alkaline catalyst, and reacting to obtain the curcumin chain extender.
  6. 6. The preparation method according to claim 4, wherein the curcumin polyurethane prepolymer has a structural general formula shown in the following formula (4): (4); Wherein R 1 is the residue of one or more diisocyanates in TDI, HDI, MDI, IPDI, R 2 is the residue of dihydric alcohol, m 2 is an integer from 10 to 50, m 3 is an integer from 10 to 50, m 4 is an integer from 1 to 50, and E is a polyurethane repeating unit segment.
  7. 7. The preparation method of the polyether amine modified curcumin according to claim 4, comprising the following steps: Mixing curcumin and polyetheramine in a polar solvent, and reacting to obtain the polyetheramine modified curcumin.
  8. 8. Use of a curcumin-based polyurethane material according to any one of claims 1-3 in medical devices or food packaging.
  9. 9. A prosthesis comprising the curcumin-based polyurethane material as claimed in any one of claims 1 to 3.

Description

Polyurethane material based on curcumin and preparation method and application thereof Technical Field The invention belongs to the technical field of high polymer materials, and particularly relates to a polyurethane material based on curcumin, and a preparation method and application thereof. Background Thermoplastic Polyurethane (TPU) is a polymeric material polymerized by the co-reaction of diisocyanate, a macromolecular polyol and a chain extender, which consists of soft segments and hard segments, which are connected by covalent bonds along a linear macromolecular backbone, and which can be made from different original molecular components. TPU has very good stability, chemical resistance, rebound resilience and mechanical properties, has smaller compression set and is widely used in the construction, automotive, aerospace, shoemaking industries, adhesives, coatings, synthetic leather and medical industries. In recent years, bio-based TPU made with renewable molecular building blocks have been used in the biomedical field due to their high tunability, mechanical properties of responsiveness, controlled biodegradation, and formation of low toxic residues. But has higher requirements on the biocompatibility and antibacterial property of materials in the medical field, especially in the aspect of in vivo tissue engineering scaffolds. The polyurethane material with the antibacterial effect is mostly prepared by adding antibacterial agents into the polyurethane material for blending, wherein the added antibacterial agents are nano silver particles, nano zinc oxide, nano titanium oxide, quaternary ammonium salt, quaternary phosphonium salt, pyridine compounds, biguanides, alcohols, phenols, aldehydes, organic acids, halogen-containing compounds and the like. The antibacterial polyurethane material prepared by physically blending the antibacterial agent and polyurethane has the defects that the antibacterial agent has certain toxicity, the load of the antibacterial agent is low by the physical blending method, the release of the antibacterial agent is difficult to control, and the aim of long-acting antibacterial is not achieved. Disclosure of Invention The present invention aims to solve at least one of the technical problems in the prior art described above. Therefore, the polyurethane material based on the curcumin contains high-content natural antibacterial and anti-inflammatory component curcumin, can effectively control the slow release of the curcumin, and has long-acting antibacterial and anti-inflammatory effects. The first aspect of the invention provides a polyurethane material based on curcumin, which is prepared from the following raw materials of a chain extender of curcumin and polyether amine modified curcumin; The curcumin chain extender has a structural general formula shown in the following formula (1): a compound wherein R is a terminal or side chain containing one or more hydroxyl groups; the structural general formula of the polyether amine modified curcumin is shown as the following formula (2): Wherein n 1 is an integer from 1 to 50 and R 0 is H or a-CH 3 group. Preferably, the structural general formula of the curcumin-based polyurethane material is shown as the following formula (3): Wherein R 1 is diisocyanate, R 2 is dihydric alcohol, m 2 is an integer of 10-50, m 3 is an integer of 10-50, m 4 is an integer of 1-50, E is a polyurethane repeating unit chain segment, and F is polyether amine modified curcumin. Preferably, the curcumin chain extender is selected from one or more of the following compounds: preferably, the polyetheramine modified curcumin is selected from one or more of the following compounds: The second aspect of the invention provides a preparation method of the polyurethane material based on curcumin, comprising the following steps of dissolving the curcumin chain extender in a polar solvent, mixing with dihydric alcohol, diisocyanate and HDI trimer, and reacting to obtain curcumin polyurethane prepolymer; and mixing the polyether amine modified curcumin and the curcumin polyurethane prepolymer, and reacting to obtain the curcumin-based polyurethane material. Preferably, the preparation method of the curcumin-based polyurethane material comprises the following steps: Dissolving the curcumin chain extender in a polar solvent, adding dihydric alcohol and diisocyanate, stirring and reacting for 1-24 hours at 30-70 ℃, then adding HDI trimer, stirring and reacting for 3-24 hours at 40-60 ℃ to obtain a curcumin polyurethane prepolymer; Mixing the polyether amine modified curcumin and curcumin polyurethane prepolymer, and reacting to obtain the curcumin-based polyurethane material Preferably, the mass ratio of the curcumin chain extender in the curcumin polyurethane prepolymer is 0.5-40%. More preferably, the curcumin chain extender accounts for 10-20% of the curcumin polyurethane prepolymer by mass. Preferably, the preparation method of the curcumin chain extender compr