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Dihydric alcohol containing acylhydrazone bond, dihydric alcohol containing acylhydrazone bond and disulfide bond, self-repairing polyurethane elastomer and preparation method thereof

A technology of polyurethane elastomer and polyurethane prepolymer is applied in the field of self-healing polyurethane elastomer and its preparation, and achieves the effects of simple preparation method, strong performance controllability and high self-healing efficiency

Active Publication Date: 2016-11-16
QINGDAO UNIV OF SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, there is no report in the relevant literature on the use of acylhydrazone bonds or the use of acylhydrazone bonds and disulfide bonds to prepare solvent-free bulk polymers that can achieve self-healing at room temperature.

Method used

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  • Dihydric alcohol containing acylhydrazone bond, dihydric alcohol containing acylhydrazone bond and disulfide bond, self-repairing polyurethane elastomer and preparation method thereof
  • Dihydric alcohol containing acylhydrazone bond, dihydric alcohol containing acylhydrazone bond and disulfide bond, self-repairing polyurethane elastomer and preparation method thereof
  • Dihydric alcohol containing acylhydrazone bond, dihydric alcohol containing acylhydrazone bond and disulfide bond, self-repairing polyurethane elastomer and preparation method thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0031] The preparation method of the dihydric alcohol containing acylhydrazone bond comprises the following steps: dissolving 20-30 parts by weight of hydroxyaldehyde in isopropanol, dissolving 10-20 parts by weight of dihydrazide compound in ice In the acetic acid, the isopropanol and glacial acetic acid are mixed in a weight part of 120-150 parts by weight, and reacted at 50°C-70°C to obtain a dihydric alcohol containing an acylhydrazone bond. In the mixed solution of isopropanol and glacial acetic acid, isopropanol: glacial acetic acid (weight ratio) = 1:2-1:5.

[0032] The present invention also provides dihydric alcohols containing acylhydrazone bonds and disulfide bonds, which are obtained by reacting the following raw materials in parts by weight: 20-40 parts of dithiolipid monomers, 40-60 parts of hydrazine hydrate and 20- 30 parts of hydroxy aldehydes, in parts by weight.

[0033] The dithiolipid monomers are 3,3'-dithiodipropionic acid dimethyl ester, 2,2'-dithiodia...

Embodiment 1

[0040] Embodiment 1: Preparation contains the dibasic alcohol of acylhydrazone bond

[0041] Dissolve 24.4g of p-hydroxybenzaldehyde (0.2mol-CHO) in 48.8g of isopropanol, and dissolve 17.4g of adipic acid dihydrazide (0.2mol of hydrazide group) in 87.0g of glacial acetic acid; mix the two The solution was mixed evenly and reacted at 70°C for 1 h under stirring at 250 rpm. Filtration under reduced pressure, the obtained product was washed with 150g ethanol (3 times, 50g each time) and 600g deionized water (3 times, 200g each time) successively under heating at 70°C, and dried to obtain a dihydrazone bond-containing Alcohol, that is, p-hydroxybenzaldehyde adipyl hydrazone. The product is light yellow solid powder. The productive rate is 96%, and its infrared spectrogram is as follows figure 1 As shown, the molecular structural formula of the product obtained is as follows:

[0042] .

Embodiment 2

[0043] Embodiment 2: Preparation contains the dibasic alcohol of acylhydrazone bond and disulfide bond

[0044] 1. Preparation of 3,3'-dithiobis(propionohydrazide)

[0045] Take 29.90 g of dimethyl 3,3'-dithiodipropionate and dissolve it in 60 g of methanol, then add 60 g of hydrazine hydrate, and stir at room temperature for 1 h. The product was filtered with quantitative filter paper under reduced pressure, and the obtained product was washed with 100 g of methanol, 100 g of deionized water, and 100 g of methanol in sequence, filtered, and dried to obtain 24.68 g of 3,3'-dithiobis(propionohydrazide). Yield 86%. The product is a white solid powder, and the molecular structural formula of 3,3'-dithiobis(propionohydrazide) is as follows:

[0046] .

[0047] 2. Preparation of dihydric alcohols containing acylhydrazone bonds and disulfide bonds

[0048] Get p-Hydroxybenzaldehyde 24.4g and dissolve in 48.8g isopropanol, get 3,3'-dithiobis(propionohydrazide) 23.8g that embodi...

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Abstract

The invention provides dihydric alcohol containing an acylhydrazone bond, dihydric alcohol containing an acylhydrazone bond and a disulfide bond, a self-repairing polyurethane elastomer and a preparation method thereof. The polyurethane elastomer is prepared from the dihydric alcohol containing the acylhydrazone bond or the dihydric alcohol containing the acylhydrazone bond and the disulfide bond and a polyurethane prepolymer. The dihydric alcohol containing the acylhydrazone bond is prepared from a dihydrazide monomer and hydroxy aldehyde. The dihydric alcohol containing the acylhydrazone bond and the disulfide bond is prepared from a dithio lipid monomer, hydrazine hydrate and hydroxy aldehyde. The polyurethane prepolymer is prepared from a polyester or polyether polyol monomer and diisocyanate. After the self-repairing polyurethane elastomer is mechanically damaged, the acylhydrazone bond or the disulfide bond on a crosslinked polymer molecular chain achieves material self-repairing through dynamic exchange reaction. The self-repairing crosslinked polyurethane elastomer material is simple in preparation, can achieve self repairing at room temperature, is high in repairing capability, short in repairing time and capable achieving many times of self repairing and has better mechanical properties.

Description

technical field [0001] The invention relates to a preparation method of a polyurethane elastomer, in particular to a dihydric alcohol containing an acylhydrazone bond, a dihydric alcohol containing an acylhydrazone bond and a disulfide bond, a self-repairing polyurethane elastomer and a preparation method thereof. Background technique [0002] Self-healing materials are a new type of material that can repair itself when an object is damaged. At present, polymer-based self-healing systems can be divided into two types: one is external aid self-healing, that is, microcapsules, liquid-core fibers or capillary networks loaded with repairing agents are embedded in the matrix material, and external damage causes microcapsules, liquid-cored fibers, etc. The core fiber and capillary network are broken, and the liquid repair agent is released into the crack and then solidifies, thereby completing the repair of the crack; one is intrinsic self-healing, which is to introduce reversible...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G18/48C08G18/10C08G18/38C08G18/66C07C249/16C07C251/86C07C319/22C07C323/60
CPCC07C249/16C07C251/86C07C319/22C07C323/60C08G18/10C08G18/4825C08G18/4829C08G18/6696C08G18/3819C08G18/3857
Inventor 魏燕彦白亚朋
Owner QINGDAO UNIV OF SCI & TECH
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