Synthesis of Novel Reactive Disperse Silicon-Containing Dyes and Their Coloring Properties on Silicone Rubbers

Molecules. 2018 Jan 9;23(1):127. doi: 10.3390/molecules23010127.

Abstract

Novel red and purple reactive disperse silicon-containing dyes were designed and synthesized using p-nitroaniline and 6-bromo-2,4-dinitro-aniline as diazonium components, the first condensation product of cyanuric chloride and 3-(N,N-diethyl)amino-aniline as coupling component, and 3-aminopropylmethoxydimethylsilane, 3-aminopropylmethyldimethoxysilane, and 3-aminopropyltrimethoxysilane as silicone reactive agents. These dyes were characterized by UV-Vis, ¹H-NMR, FT-IR, and MS. The obtained reactive disperse silicon-containing dyes were used to color silicone rubbers and the color fastness of the dyes were evaluated. The dry/wet rubbing and washing fastnesses of these dyes all reached 4-5 grade and the sublimation fastness was also above 4 grade, indicating outstanding performance in terms of color fastness. Such colored silicone rubbers showed bright and rich colors without affecting its static mechanical properties.

Keywords: coloring; reactive disperse dyes; silicone group; silicone rubber.

MeSH terms

  • Aniline Compounds / chemistry*
  • Color
  • Coloring Agents / chemical synthesis*
  • Molecular Structure
  • Propylamines / chemistry*
  • Proton Magnetic Resonance Spectroscopy / methods
  • Silanes / chemistry*
  • Silicone Elastomers / chemistry*
  • Spectrophotometry / methods
  • Spectroscopy, Fourier Transform Infrared / methods
  • Structure-Activity Relationship

Substances

  • Aniline Compounds
  • Coloring Agents
  • Propylamines
  • Silanes
  • Silicone Elastomers
  • 3-aminopropyltrimethoxysilane
  • 4-nitroaniline