Preparation of covalently colored polymer latex through miniemulsion polymerization based on a polymerizable dye

Abstract

A polymerizable red dye 1-(6-acrylamidohexylamino) anthraquinone (AHAQ) was synthesized and used to prepare colored polymer latexes using styrene and butyl acrylate as main monomers. Influences of the initiator and surfactant amounts, oil/aqueous phase ratio, and AHAQ content on the polymerization process, the particle size, and surface tension of the resulted latex were investigated, and the migration resistance and light fastness of the red latex films were determined. Results showed that the polymerization was carried out smoothly, and the miniemulsion polymerization mechanism was confirmed by monitoring the dimensions of oil phase before and after polymerization. The latex particle size can be adjusted by varying the surfactant amount, and when AHAQ content was 0.2-1 wt% of total monomers, the encapsulation efficiency and dye conversion could be achieved to 98.7 and 96.3%, respectively. The UV-vis spectra of AHAQ and its corresponding covalently colored polymer indicated that the maximum absorption peak was the same, meaning that the chemical structure of chromophore in AHAQ maintains unchanged after undergoing polymerization. The migration resistance and light fastness of the covalently colored latex films were much better than that of the correspondingly non-covalently colored ones.

Preparation of dyed polymer microspheres by a physical–chemical dual-binding method and their application in lateral flow immunoassay

“…The traditional preparation methods of dyed microspheres can be divided into two categories according to the combination of microspheres and dyes: (1) physical methods, including the swelling method [21][22][23] and embedding method; [24][25][26] (2) chemical methods, including the copolymerization method [27][28][29] and surface covalent bonding method. [30][31][32] The swelling method typically penetrates the dye into the polymer chain with the organic solvent, and then the dyes are immobilized aer selectively removing the swelling agent.…”

Preparation of Covalent and Solvent-resistance Colored Latex Particles and Its Application on Cotton Fabric

“…Compared with traditional colored latex particles prepared by encapsulation and mixing, the method of obtaining covalent colored latex particles [2,18] by chemical bonds between the colorants and different polymer compositions can efficiently settle the above problem. For example, Jin [19] fabricated covalent colored PU latexes with pendent chromophores on the PU backbone. By the covalent incorporation of chromophores with PU matrix, the covalent colored PU latex films showed superior light fastness compared with the corresponding non-covalent colored PU latex films.…”

Preparation and properties of a novel polymerizable amphiphilic anthraquinone derivative and its cationic colored copolymer latexes

“…We found that the latex stability and the light fastness of the latex lms were improved signicantly by covalently bonding chromophores on the polymer chains. [32][33][34] However, since the synthesized dyes had poor solubility both in water and in monomers such as styrene and acrylates, the migration of dye molecules from the monomer droplets to the latex particles was hindered during emulsion polymerization, which induced unstable polymerization, low dye conversion and insufficient color depth of the latexes. 35,36 In the present work, 4-((4-(p-toluidino)anthraquinone-1-yl) oxy)-N-(2-(methacryloyloxy)ethyl)-N,N-dimethylbutan-1-aminium bromide (TAQMAB), a polymerizable amphiphilic anthraquinone derivative with the functionalities of both dye and surfactant, was rst designed and synthesized, and then using 2,2 0azobis(2-methylpropionamide) dihydrochloride (AIBA) as initiator, the semi-continuous emulsion copolymerization of styrene (St), butyl acrylate (BA) and TAQMAB was carried out to fabricate covalently colored P(St-BA-TAQMAB) latexes.…”