Phenolic resins sulfonation

Sulfonated chromium humate, sulfonated phenolic resin. [1716]... 

Electrical charge density is increased, such as sulfonated phenolic resin, carboxymethylcellulose, and hydrolyzed polyacrylonitrile... 

Tests showed that a fluid loss additive on a base of a sulfonated tannic-phenolic resin is effective for fluid loss control at high temperature and pressure, and it exhibits good resistance to salt and acid [868]. 

Demulsifying agent Solution of a sulfonic acid, a phenolic resin, and alcohol 5 to 15... 

N. Huang. Synthesis of fluid loss additive of sulfonate tannic-phenolic resin. Oil Drilling Prod Technol, 18(2) 39-42,106-107, 1996. 

While "conventional positive photoresists" are sensitive, high-resolution materials, they are essentially opaque to radiation below 300 nm. This has led researchers to examine alternate chemistry for deep-UV applications. Examples of deep-UV sensitive dissolution inhibitors include aliphatic diazoketones (61-64) and nitrobenzyl esters (65). Certain onium salts have also recently been shown to be effective inhibitors for phenolic resins (66). A novel e-beam sensitive dissolution inhibition resist was designed by Bowden, et al a (67) based on the use of a novolac resin with a poly(olefin sulfone) dissolution inhibitor. The aqueous, base-soluble novolac is rendered less soluble via addition of -10 wt % poly(2-methyl pentene-1 sulfone)(PMPS). Irradiation causes main chain scission of PMPS followed by depolymerization to volatile monomers (68). The dissolution inhibitor is thus effectively "vaporized", restoring solubility in aqueous base to the irradiated portions of the resist. Alternate resist systems based on this chemistry have also been reported (69,70). 

Materials. Epoxy novolac, DEN-431, obtained from Dow Chemical Co. was selected as the epoxy component. A 3,3 -diazidodiphenyl sulfone synthesized in our laboratory (5) was used as the azide compound. Poly(/7-vinyl phenol) obtained from Maruzen Oil Co. was used as the phenolic resin matrix. The coating solvent was cyclohexanone. The developer used in this study was 0.1 N tetramethylammonium hydroxide aqueous solution. 

ButylatedPhenols and Cresols. Butylated phenols and cresols, used primarily as oxidation inhibitors and chain terminators, are manufactured by direct alkylation of the phenol using a wide variety of conditions and acid catalysts, including sulfuric acid, -toluenesulfonic acid, and sulfonic acid ion-exchange resins (110,111). By use of a small amount of catalyst and short residence times, the first-formed, ortho-alkylated products can be made to predominate. For the preparation of the 2,6-substituted products, aluminum phenoxides generated in situ from the phenol being alkylated are used as catalyst. Reaction conditions are controlled to minimize formation of the thermodynamically favored 4-substituted products (see Alkylphenols). The most commonly used is -/ -butylphenol [98-54-4] for manufacture of phenolic resins. The tert- butyl group leaves only two rather than three active sites for condensation with formaldehyde and thus modifies the characteristics of the resin. 

Ferromagnetic phenol-formaldehyde sulfonic acid cation-exchange resin has been synthesized by heating a mixture of phenolsulfonic acid and formalin containing magnesium ferrite at 65 °C for 3 h. 

The sulfonic acid resins such as Dowex-50 and Amberlyst-15 have been used to promote the alkylation of the more active aromatic rings but attempts to increase their acidity generally resulted in the degradation of the solid. 2 The more strongly acidic perfluorinated resin sulfonic acid, Nafion-H,2>3 has, however, been used to promote the alkylation of benzene and other aromatic compounds. Nafion-H catalyzed the vapor phase reaction between toluene and methanol. When nm at 185°C a 12% yield of the isomeric xylenes was obtained with the ortho isomer the major product. 0 Methylation of phenol at 205°C over this catalyst gave, at 63% conversion. 37% anisole and 10% of a mixture of the ortho and para cresols in a 2 1 ratio. Reaction of anisole with methanol under these conditions resulted in a 14% selectivity to the methyl anisoles at 40% conversion, with the ortho and para isomers formed in nearly equal amounts. ... 

The LEC experiment can be performed on ion exchange resins. Sulfonated PS beads were used to absorb the transition metal cation ions. The beads of low crosslinking (4-8% divinylbenzene) gave narrow and more symmetric chromatographic peaks. A variety of cations, from + 1 to + A valency, were loaded onto the resin numerous compounds such as phenols, alcohols, sugars, nucleic... 

Phenolic compounds sulfonate very easily. Phenol reacts to the extent of 94 per cent when heated with an equimolar quantity of concentrated acid for 2 hr at 100 C. The cresols react less completely with considerable variation in isomers. These phenolic sulfonates find application for preparing tanning agents and ion-exchange resins. Chlorinated phenols are sulfonated in the preparation of dye intermediates. ... 

Other resins, such as resorcinol and cashew nut resins, other acidic catalysts, such as p-toluene sulfonic acid and other aggregates, such as asbestos, glass flakes, and slag microfibers (PMF) have been substituted for the original ingredients but basically the formulations for the relatively widely used phenolic resin mortars have not changed radically during more than a half century of satisfactory use. 

Hydrobenzyl alcohol groups as well as sulfonic acid groups on the carbon a to the aromatic rings of some of the phenylpropane units of the random polymer react in the presence of strong mineral acids with the aromatic nuclei of other phenylpropane units. This reaction, leading to diphenylmethanes, is of the same type as the formation of phenolic resins from phenol and formaldehyde. Lignin also reacts with formaldehyde and can be cross-linked by it in the same manner as that of synthetic polyphenohc resins. 

---