Polydyes

Fluorescein has a carboxyl and phenol hydroxyl group. These groups were used to poly-condense fluorescein with Me2SnCl2 via IF reactions to generate polydye, 100.230... 

An interesting variant of the polycondensation approach involved the use of fluorescent dyes as the difunctional organic monomers. Thus, soluble, high molecular weight titanium polydyes (e.g., 4/ = 5.3 x 10 by lightscattering measurements for the titanium polymer derived from the diphenol monomer bromophenol blue) were synthesized in yields that depended on the reaction conditions and the dye used. Structural characterization was... 

Another attraction for including dyes into polymers is the (potential) permanent, nonleaching nature of such polymer-containing dyes. This would allow a material that contains a polydye to remain colored for longer times even in solids such as plastics. Migration and loss of colorants occurs even in solids such as plastics. The ability to retain color or other important additive properties is especially important in marine coatings apphcations, where leaching and subsequent loss is aided by the ever present aqueous environment. 

Other related dyes were also successfully incorporated as polydyes including nigro-sine, 6. 

Indigo Carmine has also been incorporated as a polydye, 7. 

The structure of the polydye formed from titanocene dichloiide and Eriochrome Black T is given as 8. 

The polydyes were generally soluble in dipolar aprotic liquids such as HMPA, DMF, DMSO, and TEP. Polydye solutions were used to impregnate a number of items including plastics (polyethylene, polycarbonate, polypropylene, poly(vinyl chloride), polystyrene, nylon 6,6, and SAN), cloth (cotton, denim, and 50-50% polyester fabric), paper, films, and coatings. 

A similar polydye, 10, was formed from the reaction of Ru(bipy)2Cl2 and N,N -bis(3-aminophenyl)-3,4,9,10-perylenetetracarboxylic diimide. This product was formed in 85% yield and had a DP of 33,000 by light-scattering photometry. 

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