Chemical Properties
Light yellowv to yellow solid
Uses
1,3-Bis(3-aminophenoxy)benzene(10526-07-5) is an intermediate compound used in the production of synthetic materials, such as PI (polyimide) films and polyimide materials.
Application
1,3-Bis(3-aminophenoxy)benzene (APB,10526-07-5) is a diamine intermediate compound that can be used as a raw material for organic synthesis or as a component of polymer monomers. Studies have shown that APB reacts with p-benzoquinone to synthesise a novel oligomeric compound. The polymer also adheres to metals and becomes non-wetting when cured with heat. With a moisture absorption of only 0.1% by weight, it is a potential moisture barrier insulator for electronic components[1].
Preparation
1,3-Bis(3-aminophenoxy)benzene(10526-07-5) is a reactive monomer commonly utilized in the synthesis of polyurethane coatings. This compound is processed at 200 degrees Celsius and has a viscosity of 1.5-2.0 centipoise at 25 degrees Celsius. Its chemical structure consists of three amine groups that are ether linked to a benzene ring with one hydroxyl group on the phenoxy side chain. The monomer can be synthesized via acylation reaction or polymerization process, typically through heating with a catalyst. The resulting product is thermally stable and resistant to heat up to 250 degrees Celsius.
Synthesis
In the 500mL four neck flasks that have agitator, reflux exchanger and dean stark trap, add the 3-amino phenol of 71.5g (0.655mol), 49 quality % aqueous sodium hydroxide solutions, 250gDMI and the 50g toluene of 53.5g (0.655mol).Flask contents is heated to 180 ℃ and stir and to feed nitrogen simultaneously, and azeotropic is removed toluene and water.Subsequently, the flask inclusion is cooled to room temperature and transfers in the 600mL autoclave that has agitator.
Subsequently, add 1 of 34g (0.298mol), 3-two fluorobenzene; Seal this reactor; To wherein being blown into nitrogen; After this, autoclave is heated to 200 ℃; And order is reflected to be carried out under 200 ℃ 53 hours.After this, cool off this autoclave, by the reaction mixture of high efficiency liquid chromatography (after this abbreviating HPLC as) analysis part.The result is 1,3-Bis(3-aminophenoxy)benzene is 82% (with respect to 1,3-two fluorobenzene).
References
[1] K. KALEEM; S. E; F Chertok. Quinone–amine polymers. II.? 1,3-bis(3-aminophenoxy) benzene-p-benzoquinone oligomers[J]. Journal of Polymer Science Part A: Polymer Chemistry, 1989. DOI:10.1002/pola.1989.080270312.
