Anthraquinone-derived monomers

Temperature [SCH 92], pH [KAT 95], electricity [TAN 82] and light [SUZ 90] responsive polymers are of interest to researchers for a long time. 

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The phenolics include anthocyanins, anthraquinones, benzofurans, chromones, chromenes, coumarins, flavonoids, isoflavonoids, lignans, phenolic acids, phenylpropanoids, quinones, stilbenes and xanthones. Some phenolics can be very complex in structure through additional substitution or polymerization of simpler entities. Thus xanthones can be prenylated and flavonoids, lignans and other phenolics can be glycosylated. Condensed tannins involve the polymerization of procyaninidin or prodelphinidin monomers and hydrolysable tannins involve gallic acid residues esterified with monosaccharides. As detailed in this review, representatives of some major classes of plant-derived phenolics are potent protein kinase inhibitors. 

Photo-CIDNP experiments using anthraquinones as photosensitizers for oxidation of a variety of uracil- and thymine-derived cyclobutane dimers, e.g. c,s-l, t,s-l, c,a-1, t,a-l, and c,s-2, 4, and 5, demonstrated the existence of both Pyr +oPyr and its dissociation product, the monomer radical cation Pyr + [6, 7]. 

This new zeolite-catalyzed ring-shift isomerization could provide a new route to anthracene and its derivatives [Song, 1996], which are valuable chemicals in demand, from phenanthrene, which is rich in liquids from coal. Selective partial hydrogenation of phenanthrene would be needed as the first step. Possible applications of sym-OHAn include the manufacturing of anthracene (for dyestuffs and fine chemicals), anthraquinone (pulping agent), and pyromellitic dianhydride (the monomer for polyimides such as Du Pont s Kapton) [Song and Schol rt, 1993]. Fundamental research is needed to clarify the mechanisms and reaction pathways. 

The photosensitive layers of early plates were composed of acrylate/methacrylate and acrylated cellulose acetate mixtures. Other printing plates contained polyamides or nylon derivatives as binders. Generally, printing plates contain a mixture of reactive monomers and multifunctional oligomers (pre-polymers), polymeric binders, and photoinitiators with exceptional cure depth. The original photoinitiators were benzoin derivatives. Later, anthraquinone and other systems were used. 

Determination of intermediates in dye synthesis (anthraquinone and derivatives), azo dyes in intermediates, products, coloring solutions and industrial effluents. Determination of aggregation number of textile dyes. Determination of food colors (e.g., of tartrazine type) in soft drinks Determination of monomers (aldehydes, acrylamide, acrylonitrile, isocyanates, methyl methacrylate, styrene, vinyl acetate) in final products and industrial effluents. Determination of initiators (azodiisobutyinitrile, benzoyt peroxide, cyclohexylperoxydicarbonate, laurylperoxide), inhibitors (hydroquinones, butylated hydroxyanisole, 4-f-butyl phenolsulphide, AAphenyt- -naphthylamine) and organo-tin stabilizers in PVC plastics... 

Several 2-substituted derivatives of anthraquinones were also compared in photoactivity, subject to the nature of the light source, the amine co-synergist and the type of the monomer used. All were found to be effective triplet state initiators. The anthraquinones, however, with electron withdrawing substituents were more active. This suggests that electron transfer is also an important part of the process of initiation. In addition, when halogen substituents are present, upon irradiation they give rise to halogen radicals and further enhance the polymerization rate. ... 

Andrieux, C. P., Audebert, R, and Saveant, J. M., Studies of modified electrodes starting from pyrrole monomers derivated by anthraquinone, phenothiazine or anthracene moieties on the nitrogen or in the 3-position, synthesis, cyclic voltammetry and a study of charge-transfer reactions, Synth. Metals, 35, 155-158 (1990). 

The mesogenic acrylate monomers were prepared by procedures described in the literature (phenylbenzoate-, phenylcyclohexane-, biphenyl-derivatives, azo dye monomer ). The anthraquinone monomer was synthesized by Dr Etzbach, BASF, Ludwigshafen. 

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