Functional high performance colorants

Abstract

This work deals with organic colorants with anti-corrosion and antimicrobial properties. This work has 4 parts. 1. A series of pigments were prepared by reacting azobarbituric acid with nickel chloride or zinc chloride, and the resulting pigments were analyzed and tested. Special attention was paid to the commercial Pigment Yellow 150. The manufacturers of this pigment describe it as a complex of Ni2+ and azobarbituric acid with the addition of melamine. In this work, a new production process was developed, which is protected by patent CZ 304515 B6 20140611, and the pigment produced by this process is in the portfolio of Synthesia as. under the name Versal Yellow 9GP. 2. Perylene pigments were prepared by reacting perylenetetracarboxylic dianhydride with methylamine (Pigment Red 179 2,9-dimethylanthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetraone) or with 3,5-dimethylaniline (Pigment Red 149 2,9-bis(3,5-dimethylphenyl)anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetraone) or with 2-phenethylamine (Pigment Black 31 2,9-diphenethylanthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetraone). As it turned out that the prepared pigments (ad. 1, ad. 2) do not have anti-corrosion or antimicrobial properties, additives with these properties were subsequently synthesized in this work. 3. A number of anti-corrosion inhibitors (pigments) were prepared by reacting perylenetetracarboxylic acid dianhydride with magnesium chloride or zinc chloride. Testing has shown that magnesium perylene-3,4,9,10-tetracarboxylate exhibits excellent anti-corrosion properties. This corrosion inhibitor is protected by patent CZ 308991 (2020). Furthermore, a series of magnesium complexes with azo ligands, prepared by the diazo-coupling reaction of anthranilic acid with 5-methyl-2-phenyl-3-pyrazolone (yellow, (E)-2-((5-hydroxy-3-methyl-1-phenyl- 1H-pyrazol-4-yl)diazenyl)benzoic acid), anthranilic acids with naphthol AS-PH (red, (E)-2-((3-((3-ethoxyphenyl)carbamoyl)-2-hydroxynaphthalen-1-yl )diazenyl)benzoic acid), anthranilic acid with 2-naphthol (red, (E)-2-((2-hydroxynaphthalen-1-yl)diazenyl)benzoic acid) and 2-amino-5-nitrophenol with naphthol AS-PH (black, (E)-N-(3-ethoxyphenyl)-3-hydroxy-4-((2-hydroxy-4-nitrophenyl)diazenyl)-2-naphthamide). Yellow (complex of magnesium and (E)-2-((5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)diazenyl)benzoic acid proved to be the most effective anti-corrosion agent. 4. Furthermore, a number of antimicrobial compounds (dyes) were prepared and tested in this work. From a chemical point of view, these antimicrobial compounds are derivatives of perylenediimide prepared by the reaction of perylenetetracarboxylic acid dianhydride or naphthalenetetracarboxylic acid dianhydride with N,N-dimethyl-1,3-propanediamine. This is followed by alkylation with iodomethane or 2-bromoethanol. Thus, highly effective antimicrobial dyes were prepared. Red 3,3'-(1,3,8,10-tetraoxo-1,3,8,10-tetrahydroanthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline- 2,9-diyl)bis(N,N,N-trimethylpropane-1-aminium) diiodide and 3,3'-(1,3,8,10-tetraoxo-1,3,8,10-tetrahydroanthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-2,9-diyl)bis(N-(2-hydroxyethyl)-N,N-dimethylpropane-1-aminium) dibromide. Furthermore, shade-free, highly effective compounds, 3,3'-(1,3,6,8-tetraoxo-1,3,6,8-tetrahydrobenzo[lmn][3,8]phenanthroline-2,7-diyl)bis(N,N,N-trimethylpropan-1-aminium) diiodide and 3,3'-(1,3,6,8-tetraoxo-1,3,6,8-tetrahydrobenzo[lmn][3,8]phenanthroline-2,7-diyl)bis(N-(2-hydroxyethyl)-N,N-dimethylpropan-1-aminium) dibromide.