A sulfonated aromatic stain resist chemical consisting of the condensation product of phenol sulfonic acid, dihydroxy diphenol sulfone, and formaldehyde was separated by semi-prep scale reverse phase high pressure liquid chromatography. Stain resistance activity was demonstrated in only two of the ten fractions that were isolated, with very slight activity in another two fractions. The active stain resist component is a low molecular weight condensation product of the sulfonic acid and sulfone with the phenolic groups converted to alkyl aryl ethers. The active component comprises only about 10% of the total weight of the stain resist chemical.Sulfonated aromatic compounds (SAC) are used in the textile industry to produce multicolor printed fabrics by preventing acid dyes from interacting with nylon and wool textiles. These materials are also extensively used to produce stain resistant carpeting by treating dyed carpet with SAC to provide resistance to staining by natural and synthetic food dyes and colorants [8]. SAC materials are normally applied at low pH to assure protonation of the sulfonic acid. At slightly acidic conditions, the treated nylon yellows, while under basic conditions, the treatment is ineffective [6]. During SAC treatment of the polyamide, only a small amount of the SAC is exhausted onto the polyamide. Several possible mechanisms for the resistance to staining of dyeing have been proposed. The sulfonic acid groups on the SAC will react with the polyamide amine groups to prevent the reaction between the acid dye and the basic amine groups. Harris and Hangey have proposed that SAC creates a ring dyeing effect that hinders dye diffusion by increasing the tortuosity of the diffusant [8]. Cook and Hajisharifi [2] proposed the electrical barrier effect created by the reacted SAC toward anionic dyes and colorants. In addition to the electrical barrier, Kamath et al.[9] demonstrated a &dquo;diffusion barrier&dquo; formation on the surface of nylon.We undertook this study to determine the chemical structure of the materials responsible for stain resistance. The particular SAC material we selected for this separation is chemically defined as a sulfonic acid substituted phenol-formaldehyde condensate, produced from reactions with 4,4'-dioxydiphenyl-sulfone, formaldehyde, and 4-hydroxybenzene sulfonic acid or naphthalene sulfonic acid or sodium sulfite or sodium hydrogen sulfite in molecular ratios of 1:0.7-1.1 or 0.7-0.2 [5]. It is available commercially from Mobay Chemical Co. under the trade name of Mesitol NBS.
DiscussionPhenolic resin technology is highly complex, dependant on reactant concentration, temperature, and pH. This is illustrated by the work of Sebenik and Lepanje [ 11 ].High pressure liquid chromatography (HPLC) has been used to separate and identify phenolic resins. Isocratic elution with different ratios ofdichloromethanedioxane-methanol as the mobile phase has successfully separated sixteen different components from laboratory-prepared phenolformaldehyde resins. Compounds such as pheno...