Alkanolamine esters

The present paper describes several new classes of hindered phenyl bis- and tris-phosphites having di-benzo[d,f][1,3,2]dioxaphosphepin and dibenzo[d,g]-[1,3,2]dioxaphosphocin rings. The latter compounds exhibit superior effectiveness as processing stabilizers together with greater resistance to discoloration and hydrolysis. The di- and tri-alkanolamine esters are of particular interest because of their even greater resistance to hydrolysis at 50°C for extended time periods previously achievable only in the case of certain di-hindered phenyl phosphonites. 

SCHEME 1.6 Three routes to cationic derivatives including fatty acid to nitrile to alkyl amine (fop), fatty acid to alkanolamine ester (center), and olefin to alkyl bromide to alkyl dimethyl amine (bottom). 

Copper and many of its ciUoys resist corrosive attack by most organic compounds such as amines, alkanolamines, esters, glycols, ethers, ketones, alcohols, aldehydes, naphtha, gasoline, and most organic solvents. 

Esterquats with improved stability and biodegradability are prepared by quaternization of a fatty acid (partially hydrogenated tallow) alkanolamine ester with an alkylating agent (dimethyl sulfate) in the presence of nonionic emulsifiers [126] or cosmetic oils [159]. This procedure avoids problems associated with the use of lower alcohols as solvents in the reaction, such as low ignition point, poor emulsifying capacity for perfume oils, poor skin compatibility, and a defatting action on the skin. Formulations of a triethanolamine-based Coco esterquat, oil, and a Ci-Cg alcohol are useful in cosmetic and sunscreen formulations [160]. 

ALKANOLAMINES - ALKANOLAMINESFROMNITROALCOHOLS] (Vol2) -esters of lactate salts [HYDROXYCARBOXYLIC ACIDS] (Vol 13)... 

Reaction with Fatty Acids and Esters. Alkanolamines and long-chain fatty acids react at room temperature to give neutral alkanolamine soaps, which are waxy, noncrystaUine materials with widespread commercial appHcations as emulsifiers. At elevated temperatures, 140 —160°C, A/-aIkanolamides are the main products, at a 1 1 reaction ratio (7,8). 

Reaction with Acid Anhydrides. Below room temperature, acid anhydrides react with alkanolamines to produce amides, which partially rearrange to esters on warming to room temperature or slighdy above. 

On heating, an alkanolamine soap first dehydrates to the amide this is also obtained from the methyl ester of the fatty acid by heating with the alkanolamine at 60°C in the presence of a catalytic amount of sodium methoxide. Methanol is removed under partial vacuum. At higher temperature, the amide is dehydrated to an oxa2oline. 

In the lightening of petroleum hydrocarbon oil, esters of mercaptocarboxyhc acids can modify radical behavior during the distillation step (58). Thioesters of dialkanol and trialkanolamine have been found to be effective multihinctional antiwear additives for lubricants and fuels (59). Alkanolamine salts of dithiodipropionic acid [1119-62-6] are available as water-soluble extreme pressure additives in lubricants (60). 

Titanium chelates are formed from tetraalkyl titanates or haUdes and bi- or polydentate ligands. One of the functional groups is usually alcohoHc or enoHc hydroxyl, which interchanges with an alkoxy group, RO, on titanium to Hberate ROH. If the second function is hydroxyl or carboxyl, it may react similarly. Diols and polyols, a-hydroxycarboxyflc acids and oxaUc acid are all examples of this type. P-Keto esters, P-diketones, and alkanolamines are also excellent chelating ligands for titanium. 

ESTERS OF AMINOBENZOIC ACIDS AND ALKANOLAMINES a. Derivatives of Ethanolamine... 

A chance observation made some time prior to the full structural elucidation of cocaine in fact led to one of the more important lasses of local anesthetics. It was found that the simple ethyl e. ter of p-aminobenzoic acid, benzocaine (25), showed activity. 1-. a local anesthetic. It is of interest to note that this drug, I 1rst introduced in 1903, is still in use today. Once the struc-iiire of cocaine was established, the presence of an alkanolamine iiiniety in cocaine prompted medicinal chemists to prepare esters "I aminobenzoic acids with acyclic alkanolamines. Formula 26 11 presents the putative relationship of the target substances with cocaine. 

A special application of the ether carboxylic acid in metalworking has been described by Schuster [46] a boric acid ester has been produced by condensation of boric acid, alkanolamine, and alkyl ether carboxylic acid, eventually combined with a fatty acid. This condensation product gives less Ca soap precipitation, good anticorrosion effect, better removability of residues, and cleaner apparatus than the condensation product using only fatty acid. 

Surfactants are also prepared by the reaction of glycerol derivatives RC02 [CH2CH(0H)CH20] H (R = C6 16 alkyl, n = 1-5) with P4O10 at 60-80°C with subsequent neutralization of the resulting phosphate ester acids with aqueous alkali or alkanolamine solution at 50-70°C [10]. 

Amine salts of acrylate ester polymers, which are physiologically acceptable and useful as surfactants, are prepared by transesterifying alkyl acrylate polymers with 4-morpholinethanol or alkanolamines and fatty alcohols or alkoxyl-ated alkylphenols and neutralizing with phosphoric acid. This polymer salt (pH of a 10% aqueous solution = 5.1) was used as an emulsifying agent for oils and waxes [70]. 

The development of monoalkyl phosphate as a low skin irritating anionic surfactant is accented in a review with 30 references on monoalkyl phosphate salts, including surface-active properties, cutaneous effects, and applications to paste and liquid-type skin cleansers, and also phosphorylation reactions from the viewpoint of industrial production [26]. Amine salts of acrylate ester polymers, which are physiologically acceptable and useful as surfactants, are prepared by transesterification of alkyl acrylate polymers with 4-morpholinethanol or the alkanolamines and fatty alcohols or alkoxylated alkylphenols, and neutralizing with carboxylic or phosphoric acid. The polymer salt was used as an emulsifying agent for oils and waxes [70]. Preparation of pharmaceutical liposomes with surfactants derived from phosphoric acid is described in [279]. Lipid bilayer vesicles comprise an anionic or zwitterionic surfactant which when dispersed in H20 at a temperature above the phase transition temperature is in a micellar phase and a second lipid which is a single-chain fatty acid, fatty acid ester, or fatty alcohol which is in an emulsion phase, and cholesterol or a derivative. 

Adhesives, 1 501-502, 524-553. See also Adhesion Pressure-sensitive adhesives (PSAs) acrylic ester polymers, 1 390 alkanolamines from olefin oxides and ammonia, 2 135... 

Marine coatings Organic coatings for corrosion control Paint acrylic ester polymers, 7 388-389 adhesion, 7 90-92 advanced ceramic, 7 704-705 alkanolamines from olefin oxides and ammonia, 2 136 alkyd resins, 2.T67-168 amino acid resin applications, 2 635—637 anticorrosion, 25 134 anticorrosion metallic, 7 713-714... 

Water Hyacinth. Water hyacinth (Eichornia crassipes Solms) has been killed by 0.1% solution of the alkanolamine salt of 2,4-D in Indonesia (54), or in the Philippines by the isopropyl ester in as low as 0.1% solutions (39). In the southern United States, 2,4-D has been widely used to kill this plant. This plant is of relatively minor importance in Puerto Rico. It tends to choke up river mouths and is removed to improve drainage. A single application of the isopropyl ester of 2,4-D has given excellent results on a small scale. 

Ester quats with one, two, or three fatty acid ester moieties exist in the molecule, but the dominating type are the diester quats, i.e., products that contain two fatty acid ester chains and two short alkyl groups. These are synthesized by reaction of two moles of fatty acid with one mole of alkanolamine using an acid catalyst under conditions where water is stripped off The fatty... 

Alkoxylation with, for example, propylene oxide (PO). Preferred amine is triethanolamine, or ammonia and other alkanolamines used amine can also be quaternized Best example is triethanol with 14.9 PO units Contains vinyl ester acetal functionalities besides some unreacted vinyl alcohol monomer units. Preferred aldehyde is butyraldehyde Backbone, for example, polyalkylene glycol, polyalkyl-eneimine, polyether, or polyurethane, and active functional side groups made from grafting VP or VCap to backbone using radical initiators TBA (tributylammonium groups)... 

Alkanolamides are produced by condensation of fatty esters or acids with an alkanolamine. The monoalkanolamides account for 30% of market while diethanolamides account for the bulk of the rest with the balance being made up of a few specialised materials. 

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