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Hydroxyl carborane derivative containing ether bond, and modified curing agent, preparation method and application thereof

A technology of hydroxycarborane and derivatives is applied in the field of solvent-based two-component polyurethane curing agents, which can solve the problems of limitation, difficult reaction, and high viscosity in preparation, and achieve the effects of fast drying speed, improved performance, and improved storage time.

Active Publication Date: 2021-07-13
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The introduction of carborane structure can significantly improve the properties of polyurethane materials such as high and low temperature resistance, flexibility, and adhesive strength. However, due to the presence of two active hydrogen atoms in o-carborane, the preparation viscosity is large and the reaction is difficult to control; carborane There are many studies on alkyl polyarylates, but the research and application of how to introduce carborane structure into isocyanate curing agent structure is relatively limited

Method used

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  • Hydroxyl carborane derivative containing ether bond, and modified curing agent, preparation method and application thereof
  • Hydroxyl carborane derivative containing ether bond, and modified curing agent, preparation method and application thereof
  • Hydroxyl carborane derivative containing ether bond, and modified curing agent, preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0052] Preparation of hydroxycarborane derivatives containing ether linkages:

[0053] Under an argon atmosphere, a diethyl ether solution of o-carborane (28 g) was put into a 2L reaction kettle, and the system was cooled to -40°C. Then, a hexane solution of n-butyllithium (13 g) was gradually added dropwise to the system, and kept stirring at -40° C. for 20 min. Dried methyl formate (6 mL) was added to the system, the temperature of the system was raised to 25° C., and stirring was continued for 12 h. Add 300 mL of dilute hydrochloric acid solution to quench the reaction, and continue stirring for 30 min. The mixture was taken out, and the organic phase was extracted with diethyl ether, and then the extracted organic phase was subjected to a rotary evaporator to remove residual water and diethyl ether components to obtain 26 g of o-carborane B-1 containing a monoaldehyde group.

[0054] Dissolve 26g of B-1 in methanol solution, cool the system temperature to 0°C, then add s...

Embodiment 2

[0058] Preparation of hydroxycarborane derivatives containing ether linkages:

[0059] Under an argon atmosphere, a diethyl ether solution of o-carborane (28 g) was put into a 2L reaction kettle, and the system was cooled to -40°C. Then, a hexane solution of n-butyllithium (13 g) was gradually added dropwise to the system, and kept stirring at -40° C. for 20 min. Dried methyl formate (6 g) was added to the system, the temperature of the system was raised to 25° C., and stirring was continued for 12 h. Add 300 mL of dilute hydrochloric acid solution to quench the reaction, and continue stirring for 30 min. The mixture was taken out, and the organic phase was extracted with diethyl ether, and then the extracted organic phase was subjected to a rotary evaporator to remove residual water and diethyl ether components to obtain 26 g of o-carborane B-1 containing a monoaldehyde group.

[0060] Dissolve 26g of B-1 in methanol solution, cool the system temperature to 0°C, then add so...

Embodiment 3

[0064] Preparation of hydroxycarborane derivatives containing ether linkages:

[0065] Under an argon atmosphere, a diethyl ether solution of o-carborane (28 g) was put into a 2L reaction kettle, and the system was cooled to -40°C. Then, a hexane solution of n-butyllithium (13 g) was gradually added dropwise to the system, and kept stirring at -40° C. for 20 min. Add the dried 2-(2-bromoethyl)-1,3-dioxolane (18g) into the system, raise the temperature of the system to 25°C, continue stirring for 12h, then add 2g of p-toluene to the organic phase Sulfonic acid, continue to stir the reaction for 1h. Add 300 mL of saturated ammonium chloride solution to quench the reaction, and continue stirring for 30 min. The mixture was taken out, the organic phase was extracted with diethyl ether, and then the product after the formylation reaction was removed by a rotary evaporator to remove residual water and diethyl ether components to obtain 36 g of o-carborane B-1 containing a monoalde...

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Abstract

The invention discloses a hydroxyl carborane derivative containing an ether bond, a modified curing agent a preparation method and application of the hydroxyl carborane derivative. The structural formula of the hydroxyl carborane derivative containing the ether bond is one of the following formulas, wherein in the formula, an R1 group is -CH2CH2-, or an R3 group is -CH3, -CH2CH2CH3, -CH(CH3)2 and -CH2Ph. The preparation method comprises the following steps: carrying out hydroformylation on o-carborane to prepare o-carborane B-1 containing a single aldehyde group; carrying out reduction hydroxylation on the aldehyde group to prepare o-carborane B-2 containing a hydroxyl group; carrying out ring-opening reaction on the hydroxyl and epoxide to generate the hydroxyl carborane derivative containing the ether bond; and dropwise adding the derivative into an isocyanate curing agent for modification to obtain the modified curing agent. The finally obtained modified curing agent is longer in storage time, and an obtained paint film has the characteristics of high drying speed, strong flexibility and the like after the modified curing agent is mixed with resin.

Description

technical field [0001] The invention belongs to the field of solvent-type two-component polyurethane curing agent, and in particular relates to a hydroxycarborane derivative containing an ether bond, a modified curing agent, a preparation method and application thereof. Background technique [0002] Polyurethane (PU) refers to the general designation of polymers containing a large number of carbamate (-NHCOO-) structures on the main chain, and is generally formed by the cross-linking reaction of polyisocyanate curing agent and polyol resin. The main chain structure of PU is generally composed of hard segment and soft segment. Among them, the soft segment is mostly a polyol resin component, and the hard segment is a polyisocyanate curing agent. Generally speaking, by changing the ratio of hard segments and soft segments in PU, the mechanical properties and high temperature resistance of PU can be adjusted. However, traditional PU still suffers from paint film cracking and pee...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C08G18/38C09D175/04
CPCC07F5/027C08G18/288C09D175/04
Inventor 黄洪黄金泽司徒粤
Owner SOUTH CHINA UNIV OF TECH