Weaver's historic accessible collection of synthetic dyes: a cheminformatics analysis

Abstract

We present the Max Weaver Dye Library, a collection of ∼98 000 vials of custom-made and largely sparingly water-soluble dyes. Two years ago, the Eastman Chemical Company donated the library to North Carolina State University. This unique collection of chemicals, housed in the College of Textiles, also includes tens of thousands of fabric samples dyed using some of the library's compounds. Although the collection lies at the core of hundreds of patented inventions, the overwhelming majority of this chemical treasure trove has never been published or shared outside of a small group of scientists. Thus, the goal of this donation was to make this chemical collection, and associated data, available to interested parties in the research community. To date, we have digitized a subset of 2700 dyes which allowed us to start the constitutional and structural analysis of the collection using cheminformatics approaches. Herein, we open the discussion regarding the research opportunities offered by this unique library.

Fig. 1. Distribution of the set of 2196 dyes according to their color as dyes for textile fibers.

Fig. 2. Distribution of different substructures present in the 2196 digitalized dyes.

Fig. 3. Top-3 dyes retrieved by similarity search using two probes, Disperse Orange 3 and Disperse Red 11, known to cause contact dermatitis.

Fig. 4. Distribution of dyes according to their molecular weight (A) and S log P (C). Boxplot of the MW (B) and S log P (D) are shown for all dyes as well as for each individual dye color. Stars on each boxplot represent the level of significance resulting from a pairwise comparison of the particular DYE color dataset versus all others colors from *moderately significant (0.01 < P-value < 0.05), **significant (0.001 < P-value < 0.01), to ***very significant (P-value < 0.001).

Fig. 5. Circular dendrograms obtained from the hierarchical clustering of the set of 2196 dyes represented in RDKIT descriptor space. Compound nodes & names are colored according to their color (A) and their molecular weight (B).

Fig. 6. Three different pairs of dyes identified as potential “color cliffs”, i.e., compounds with highly similar structures (Tanimoto coefficient ≥ 0.95 with MACCS fingerprints) but different colors.