Jin Qingjun,Hu Yang,Shen Jie,Li Botian,Kan Chengyou
A novel green fluorescent dye, 4-hexylamino- N -(2-hydroxy-1-hydroxymethylethyl)-1,8-naphthalimide (AHHNA), was designed and synthesized, and then used as a chain extender to prepare a series of intrinsically green fluorescent polyurethane (PU) latexes. The chemical structure of AHHNA and the properties of the fluorescent PU latexes and their films were characterized. It was found that the UV–Vis and the fluorescent spectra of the PUs remained fairly consistent with AHHNA, and the fluorescence emitting capacity of 1,8-naphthalimide group was enhanced by covalently bonding AHHNA onto the PU chain. The amount of AHHNA used in the latex preparation had no obvious effect on the latex colloid properties including particle size, poly index, and zeta potential. Results showed that the color difference (Δ E ) and the extraction rate ( R
e ) of the intrinsically fluorescent PU latex film were 5.72% and 3.1%, respectively, while the Δ E and R
e of the extrinsically fluorescent PU latex film were 8.31% and 84.7%, respectively, indicating that the light fastness and the solvent fastness of the intrinsically fluorescent PU latex film were much better than those of the extrinsically fluorescent PU latex film.
In this study, three N ,4-dialkyl-substituted 1,8-naphthalimide fluorescent dyes (NPBA, NPHA, and NPOA) were synthesized in supercritical carbon dioxide (scCO 2 ) by reacting 4-bromo-1,8-naphthalic anhydride with three amines ( n -butylamine, n -hexylamine, and n -octylamine). The optimal reaction conditions and highest yields of these dyes were obtained. The yield of NPHA was 92% ± 0.57% using an organic solvent-free synthetic method. The results also indicate that the reaction time was gradually shortened by elongating the alkyl chain in the amines, and the required reaction pressure was 12 MPa or lower. Additionally, the dyeing of polyester fabrics with these three dyes was investigated using scCO 2 . The optimal dyeing time and temperature for NPBA were 70 min and 150 ℃, but they decreased at 10 gradients with the addition of two carbon atoms to the alkyl chain in the amines. The optimal dyeing pressure increased from 20 MPa to 24 MPa.
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