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Aromatic terminal hydroxyl chain extender containing acylhydrazone bond, self-repairing polyurethane and preparation method thereof

A hydroxyl-terminated chain extender and aromatic technology, which are used in the field of self-healing polyurethane and its preparation, self-repairing polyurethane, and aromatic hydroxyl-terminated chain extender, can solve the problem that repair units are not easy to uniformly disperse, unfavorable for long-term use of materials, and loss of self-repair. Repair function and other problems, to achieve the effect of good physical and mechanical properties, high self-repairing efficiency, and good mechanical properties

Active Publication Date: 2017-10-10
QINGDAO UNIV OF SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the self-healing type with external aid has the following problems: (1) it can only achieve a limited number of self-repairing of micro-cracks, and the self-repairing function will be lost when the repairing agent inside the material is released; (2) the tiny gaps generated after the repairing agent is released will It becomes a new defect of the material, which is not conducive to the long-term use of the material; (3) the repair units such as microcapsules, liquid core fibers and capillary network in the self-healing material are not easy to disperse evenly, and are prone to agglomeration, which affects the repair effect to a certain extent
However, the use of polyester polyols in self-healing polyurethane systems has not been reported yet.

Method used

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  • Aromatic terminal hydroxyl chain extender containing acylhydrazone bond, self-repairing polyurethane and preparation method thereof
  • Aromatic terminal hydroxyl chain extender containing acylhydrazone bond, self-repairing polyurethane and preparation method thereof
  • Aromatic terminal hydroxyl chain extender containing acylhydrazone bond, self-repairing polyurethane and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 11

[0030] Example 1.1: Preparation of an aromatic hydroxyl-terminated chain extender containing an acylhydrazone bond

[0031] Take 23.23g of 4-hydroxy-4-methyl-2-pentanone and dissolve in 50.00g of deionized water, and dissolve 19.42g of terephthalic acid dimethylhydrazide in 70.00g of glacial acetic acid. After mixing the two evenly, react at 70°C for 2h under stirring at 250rpm. Filtrate under reduced pressure, and vacuum-dry the resulting product to obtain an aromatic hydroxyl-terminated chain extender containing an acylhydrazone bond. The molecular structure is as shown in formula (1), named 4-hydroxy-4-methyl-2-pentanone Terephthalic acid diformylhydrazone, the product is a white solid powder. Obtain product 33.20g, productive rate 85%, its infrared spectrogram is as image 3 As shown, its NMR spectrum is shown as Figure 4 shown.

[0032]

Embodiment 12

[0033] Example 1.2: Preparation of an aromatic hydroxyl-terminated chain extender containing an acylhydrazone bond

[0034] Dissolve 13.81g of 2,5-dihydroxybenzaldehyde in 90.00g of isopropanol, and dissolve 16.82g of 3,5-dihydroxyphenylhydrazide in 30.00g of glacial acetic acid. Mix the two evenly and react at 50° C. for 4 hours under stirring at 250 rpm. Filtrate under reduced pressure, and vacuum-dry the obtained product to obtain an aromatic hydroxyl-terminated chain extender containing an acylhydrazone bond. The molecular structural formula is shown in formula (2), and it is named as 2,5-dihydroxybenzaldehyde Dihydroxybenzoylhydrazone, the product is light yellow solid powder. The product was obtained in 23.72 g, yield 82.3%.

[0035]

Embodiment 13

[0036] Example 1.3: Preparation of an aromatic hydroxyl-terminated chain extender containing an acylhydrazone bond

[0037] Dissolve 27.62g of salicylic acid in 70.00g of deionized water, and dissolve 42.00g of 3,5-dihydroxyphenylhydrazide in 50.00g of glacial acetic acid. Mix the two evenly and react at 65° C. for 2.5 hours under stirring at 250 rpm. Filtrate under reduced pressure, and vacuum-dry the obtained product to obtain an aromatic hydroxyl-terminated chain extender containing an acylhydrazone bond. , the product is light yellow solid powder. 44.68 g of the product was obtained with a yield of 77.5%.

[0038]

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Abstract

On the basis of the current situation of self-repairing polyurethane materials, the invention provides an aromatic terminal hydroxyl chain extender containing an acylhydrazone bond, self-repairing polyurethane prepared by using the aromatic terminal hydroxyl chain extender and a preparation method of the self-repairing polyurethane. Compared with dihydric alcohol containing an acylhydrazone bond, the aromatic terminal hydroxyl chain extender containing the acylhydrazone bond has the advantages that the molecular structure of the aromatic terminal hydroxyl chain extender has the large pi bond of a hydrazide benzene ring and the pi-pi conjugative effect of the pi bond of carbon-oxygen double bonds, and accordingly the chain extender is stable in structure. The prepared self-repairing polyurethane has the advantages that the molecular chain of the polyurethane contains the reversible acylhydrazone bond, can achieve self-repairing under room temperature, and is high in repairing efficiency and good in mechanical performance. The preparation of the self-repairing polyurethane has the advantages that the method is simple, raw materials are products which are commercially produced, and the prepared polyurethane is high in performance controllability and promising in application prospect.

Description

technical field [0001] The invention belongs to the field of polymer materials, in particular to self-healing polyurethane, in particular to an aromatic hydroxyl terminal chain extender containing an acylhydrazone bond, self-healing polyurethane and a preparation method thereof. Background technique [0002] Polymer materials are widely used in high-tech fields such as aviation, aerospace, electronics, and machinery because of their excellent performance. However, materials will inevitably be damaged during use, among which microcracks are the main form of material microscopic damage, and the generation of microcracks will lead to a decrease in the mechanical properties of materials and reduce the service life of materials. The self-healing function is to imitate the self-healing mechanism of biological damage to realize self-healing of the micro-cracks inside the material, avoid further damage to the material, prolong the service life of the material, and provide a new meth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G18/66C08G18/48C08G18/44C08G18/42C08G18/40C08G18/12C07C249/16C07C251/76C07C251/80C07C251/86C07C281/04
CPCC07C249/16C07C251/76C07C251/80C07C251/86C07C281/04C08G18/12C08G18/4018C08G18/4277C08G18/428C08G18/44C08G18/48C08G18/4825C08G18/4833C08G18/4854C08G18/66C08G18/3823
Inventor 魏燕彦马小越
Owner QINGDAO UNIV OF SCI & TECH
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