Alkyl phenol-formaldehyde compounds

Sorbitol and glycerine are commonly used as monomers for oxide addition. Various alkyl phenol-formaldehyde compounds are examples of polymeric acceptor compounds having a large number of unreacted hydroxyl groups. The extent of oxide polymerization can have a significant impact on performance and solubility of the dehazer or demulsifier in fuel and oil systems. 

Vulcanisation of elastomers effected by the incorporation in the compound of certain polymeric resins derived from the condensation of formaldehyde with 4-alkyl phenols. Most frequently used with butyl and EPDM compounds for enhanced heat resistance. 

Calixarenes are the products of condensation of p-alkyl-phenols and formaldehyde, which is the main route for the synthesis of these compounds. These starting materials are those used for production of bakelite, and indeed calixarenes were first made during a study of the formation of this material [28, 29]. The product isolated was assumed to be exclusively calix[4]arene. Later, after numerous studies, it was found that a mixture of calixarenes is actually formed on reaction of the corresponding ligsons, and the precise course of the reaction depends on many factors [26, 27, 30-33]. The basic variables relevant to the one-flask process in the presence of bases are as follows ... 

Hindered phenol—formaldehyde resins, that is, substituted compounds having at least the ortho positions of the phenyl blocked by alkyl groups, such as bulky branched alkyl groups, have been commercially employed as stabilizers and antioxidant additives in a wide variety of polymers [14-16[. 

Methylol-terminated para-alkyl-substituted phenol formaldehyde resin is used as the vulcanizing agent for compounds based on butyl and EPDM rubber. The alkyl group is usually octyl. It is commonly used to cure butyl rubber where superior heat resistance is needed. Therefore, this vulcanizing agent is commonly used as the curative to make butyl bladders for repetitive curing of tires. It is also sometimes used in dynamic vulcanization with a tin chloride activator to make thermoplastic vulcanizates (TPVs). 

A small amount of formaldehyde is reacted with alkylated phenols to make nonheat-reactive phenolic tackifiers, which are used to increase the building tack of rubber compounds. 

Methylphenol is converted to 6-/ f2 -butyl-2-methylphenol [2219-82-1] by alkylation with isobutylene under aluminum catalysis. A number of phenoHc anti-oxidants used to stabilize mbber and plastics against thermal oxidative degradation are based on this compound. The condensation of 6-/ f2 -butyl-2-methylphenol with formaldehyde yields 4,4 -methylenebis(2-methyl-6-/ f2 butylphenol) [96-65-17, reaction with sulfur dichloride yields 4,4 -thiobis(2-methyl-6-/ f2 butylphenol) [96-66-2] and reaction with methyl acrylate under base catalysis yields the corresponding hydrocinnamate. Transesterification of the hydrocinnamate with triethylene glycol yields triethylene glycol-bis[3-(3-/ f2 -butyl-5-methyl-4-hydroxyphenyl)propionate] [36443-68-2] (39). 2-Methylphenol is also a component of cresyHc acids, blends of phenol, cresols, and xylenols. CresyHc acids are used as solvents in a number of coating appHcations (see Table 3). 

Fig. 7-25. Main reactions of the phenolic /8-aryl ether structures during alkali (soda) and kraft pulping (Gierer, 1970). R = H, alkyl, or aryl group. The first step involves formation of a quinone methide intermediate (2). In alkali pulping intermediate (2) undergoes proton or formaldehyde elimination and is converted to styryl aryl ether structure (3a). During kraft pulping intermediate (2) is instead attacked by the nucleophilic hydrosulfide ions with formation of a thiirane structure (4) and simultaneous cleavage of the /3-aryl ether bond. Intermediate (5) reacts further either via a 1,4-dithiane dimer or directly to compounds of styrene type (6) and to complicated polymeric products (P). During these reactions most of the organically bound sulfur is eliminated as elemental sulfur.

Phenolic resins are prepared by condensation of phenolic compounds with aldehyde, commonly formaldehyde. Phenol was initially predominantly used to prepare phenolic resins, but subsequently, a greater variety of alkyl or aryl substituted phenols were explored to tailor the properties of resins by controlling functionality to meet diverse requirements of different coatings. An alkyl group substi-... 

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