Ethylene oxide with carboxyl groups

Surfactants are classified according to the ionic type of the hydrophilic group, being either anionic, cationic or nonionic. Most nonionic surfactants are made by reacting ethylene oxide with compounds containing an active hydrogen atom such as alcohols, carboxylic acids, phenols, amines or amides. 

These association reactions can be controlled. Acetone or acetonylacetone added to the solution of the polymeric electron acceptor prevents insolubilization, which takes place immediately upon the removal of the ketone. A second method of insolubiUzation control consists of blocking the carboxyl groups with inorganic cations, ie, the formation of the sodium or ammonium salt of poly(acryhc acid). Mixtures of poly(ethylene oxide) solutions with solutions of such salts can be precipitated by acidification. 

Carboxylic Acid Esters. In the carboxyflc acid ester series of surfactants, the hydrophobe, a naturally occurring fatty acid, is solubilized with the hydroxyl groups of polyols or the ether and terminal hydroxyl groups of ethylene oxide chains. 

It is well known that pMMA and pSty in THF follow ideal GPC behavior on many common GPC columns. However, many commercially important acrylate polymers contain a wide array of other monomers. In general, acrylic polymers composed of monomers that do not contain polar groups will yield well-behaved polymers, giving ideal GPC separations. Monomers that contain polar groups should prompt the analyst to carefully evaluate the possibility of adsorption of the analyte onto the column. The most common functionalities of concern are hydroxyl groups, amine groups, ethylene oxide units, and carboxylic acids. In many cases, such monomers can be tolerated. However, the acceptable level can vary considerably with even apparently minor changes in... 

The pendant hydroxy groups of ethylene oxide-propylene oxide copolymers of dihydroxy and trihydroxy alcohols may be sulfurized to obtain a sulfurized alcohol additive. This is effective as a lubricant in combination with oils and fats [387,533]. The sulfurized alcohols may be obtained by the reaction of sulfur with an unsaturated alcohol. Furthermore, fatty alcohols and their mixtures with carboxylic acid esters as lubricant components [1286] have been proposed. 

Oxidation is the first step for producing molecules with a very wide range of functional groups because oxygenated compounds are precursors to many other products. For example, alcohols may be converted to ethers, esters, alkenes, and, via nucleophilic substitution, to halogenated or amine products. Ketones and aldehydes may be used in condensation reactions to form new C-C double bonds, epoxides may be ring opened to form diols and polymers, and, finally, carboxylic acids are routinely converted to esters, amides, acid chlorides and acid anhydrides. Oxidation reactions are some of the largest scale industrial processes in synthetic chemistry, and the production of alcohols, ketones, aldehydes, epoxides and carboxylic acids is performed on a mammoth scale. For example, world production of ethylene oxide is estimated at 58 million tonnes, 2 million tonnes of adipic acid are made, mainly as a precursor in the synthesis of nylons, and 8 million tonnes of terephthalic acid are produced each year, mainly for the production of polyethylene terephthalate) [1]. 

Reduction of the carboxylic group of an AA and subsequent treatment with ethylene oxide afforded a dihydroxy derivative that cyclized in 70% sulfuric acid. From l-AAs morpholines with the (R)-configuration at the chiral center were obtained (Scheme 41) (80T409). Esters of AAs, after... 

Telechelic polymers, containing one or more end groups with the capacity to react with other molecules, are useful for synthesizing block and other copolymers [Fontanille, 1989 Hsieh and Quirk, 1996 Nuyken and Pask, 1989 Pantazis et al., 2003 Patil et al., 1998 Quirk et al., 1989, 1996 Rempp et al., 1988]. Living anionic polymers can be terminated with a variety of electrophilic reagents to yield telechelic polymers. For example, reaction with carbon dioxide, ethylene oxide, and allyl bromide yield polymers terminated with carboxyl, hydroxyl, and allyl groups, respectively. Functionalization with hydroxyl or carboxyl groups can also be achieved by reaction with a lactone or anhydride, respectively. Polymers with amine end... 

Living polymers usually require special reagents to achieve termination. Any electrophilic reagent that reacts with the carbanion active center and also allows preparation of polymers with desired terminal functionalities can be used for this purpose.168,174,181 Hydrogen-terminated polymers can be produced by proton donors, whereas carbon dioxide results in a carboxylate end group. Terminal alcohol functionalities can be formed through reaction with ethylene oxide and carbonyl compounds. 

Isophthalic acid 9, prepared by ethoxylating the phenolic group of 5-hydroxyisophtha-lic acid with ethylene oxide, was polymerized at 190°C using Bu2SnAc2 as the catalyst. The resulting carboxylic acid terminated hyperbranched polymer (not shown) was readily soluble in typical organic solvents. Due to a lower condensation temperature than that employed for the polymerization of diacid 8, evidence of anhydride bond formation was not observed. 

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