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Polyurethane material containing polythioketal soft segment and capable of being degraded with active oxygen, and preparation method thereof

A technology of polyurethane material and polyketal thiol, which is applied in the field of polyurethane material degraded by active oxygen and its preparation, can solve the problems of non-degradation of polyurethane, tissue inflammatory response, slow process, etc., and achieve good biocompatibility effect

Active Publication Date: 2019-08-30
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most traditional polyurethanes do not degrade; degradable polyurethanes mainly rely on the hydrolysis of the ester bonds in the soft segment components. This process is slow and the degradation produces acidic substances, which can easily induce tissue inflammatory reactions, and the degradation process is not environmentally responsive.

Method used

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  • Polyurethane material containing polythioketal soft segment and capable of being degraded with active oxygen, and preparation method thereof
  • Polyurethane material containing polythioketal soft segment and capable of being degraded with active oxygen, and preparation method thereof
  • Polyurethane material containing polythioketal soft segment and capable of being degraded with active oxygen, and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Step 1: Under nitrogen protection, stir 300ml of anhydrous acetonitrile, 30g of bis(2-mercaptoethyl)ether, and 0.56g of p-toluenesulfonic acid evenly, heat to reflux, and dropwise add 18.76g of 2,2- Dimethoxypropane, continue to react for 16h after the dropwise addition. After the solvent was removed by rotary evaporation, it was precipitated in ethanol three times and dried to obtain the polyketal thioketal with double-terminated mercapto groups. Its molecular weight and H NMR spectrum are as follows: figure 2 As shown, the results indicated that the polyketalthioketal was successfully synthesized.

[0030] The second step: add 1 g of the polyketal thioketal prepared in the first step to the reactor and completely remove water, add 5 ml of N,N-dimethylformamide under nitrogen protection, add 121 mg of hexamethylene diisocyanate, and then separately Add 50 ul of catalyst triethylamine and 10 ul of dibutyltin dilaurate, and heat at 80°C under nitrogen protection for 4...

Embodiment 2

[0035] Step 1: Under nitrogen protection, stir 100ml of anhydrous acetonitrile, 30g of bis(2-mercaptoethyl)ether, and 0.56g of p-toluenesulfonic acid evenly, heat to reflux, and dropwise add 18.76g of 2,2- Dimethoxypropane, continue to react for 16h after the dropwise addition. After the solvent was removed by rotary evaporation, it was precipitated in ethanol three times and dried to obtain the polyketal thioketal with double-terminated mercapto groups.

[0036] Step 2: Add 0.5 g of the polyketal thioketal prepared in the first step to the reactor, then add 0.75 g of polyethylene glycol (molecular weight 2000), completely remove water, and add 5 ml of N,N-dimethyl 221 mg of 4,4'-dicyclohexylmethane diisocyanate was added, and then 50 ul of catalyst triethylamine and 10 ul of dibutyltin dilaurate were added, and the reaction was pre-polymerized by heating at 80°C for 4 hours under the protection of nitrogen.

[0037]The third step: the temperature is lowered to 70° C., 12.6 m...

Embodiment 3

[0041] Step 1: Under nitrogen protection, stir 100ml of anhydrous acetonitrile, 30g of bis(2-mercaptoethyl)ether, and 0.56g of p-toluenesulfonic acid evenly, heat to reflux, and dropwise add 18.76g of 2,2- Dimethoxypropane, continue to react for 16h after the dropwise addition. After the solvent was removed by rotary evaporation, it was precipitated in ethanol three times and dried to obtain the polyketal thioketal with double-terminated mercapto groups.

[0042] The second step: add 0.5g of polyketal thioketal prepared in the first step to the reactor, then add 0.5g of polyethylene glycol, completely remove water, add 5ml of N,N-dimethylformamide under nitrogen protection, Add 181.4 mg of 4,4'-dicyclohexylmethane diisocyanate, and then add catalyst triethylamine 50 ul and dibutyltin dilaurate 10 ul respectively, and heat reaction at 80° C. under nitrogen protection for 4 hours for pre-polymerization.

[0043] The third step: lower the temperature to 70° C., add 10.4 mg of 1,...

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Abstract

The invention relates to a polyurethane material containing a polythioketal soft segment and capable of being degraded with active oxygen, and a preparation method thereof, wherein the polyurethane material comprises a polythioketal soft segment and a saturated aliphatic diisocyanate hard segment. The preparation steps comprise: carrying out a reaction on excess bis(2-mercaptoethyl)ether and 2,2-dimethoxypropane to prepare polythioketal; carrying out a reaction on the polythioketal and diisocyanate or on the polythioketal, polyethylene glycol and diisocyanate, and carrying out one-pot additionto obtain a prepolymer; and carrying out a diol or diamine chain extension reaction to obtain polyurethane. According to the present invention, by using the one-pot method, the polythioketal or the polythioketal and the polyethylene glycol as the soft segment are polymerized into the polyurethane; the polyurethane obtained by copolymerizing with the polyethylene glycol has amphiphilicity, and thehydrophilic / hydrophobic chain segment ratio can be adjusted through the feeding ratio; and the polyurethane can be used for producing nanoparticles, tissue engineering scaffolds or hydrogels, and issuitable for physiological environments with high active oxygen content, and has good application prospects in the biomedical field.

Description

technical field [0001] The invention relates to polyurethane and a preparation method thereof, in particular to a polyurethane material degraded by active oxygen containing a polyketal thiol soft segment and a preparation method thereof. Background technique [0002] Inflammation, as a kind of human stress response, widely occurs in various tissue parts of the human body, mainly including inflammation caused by tissue defect or immune system imbalance. Inflammatory responses are mainly caused by reactive oxygen species secreted by M1 macrophages polarized to an inflammatory phenotype or by cells in a disordered state. Active oxygen in the physiological environment includes a series of highly reactive substances such as hydroxyl radicals, superoxide anion radicals, singlet oxygen or nitrogen peroxide compounds. The sites or cells that generate reactive oxygen species also differ depending on the type of inflammation. Active oxygen in inflammation is originally used to targe...

Claims

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Application Information

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IPC IPC(8): C08G18/65C08G18/52C08G18/32C08G18/66C08G18/48C08G75/04
CPCC08G18/4833C08G18/52C08G18/6529C08G18/6674C08G75/04
Inventor 高长有张昊岚
Owner ZHEJIANG UNIV
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