Alkyl imidazolines

Many of the surfactants made from ethyleneamines contain the imidazoline stmcture or are prepared through an imidazoline intermediate. Various 2-alkyl-imidazolines and their salts prepared mainly from EDA or monoethoxylated EDA are reported to have good foaming properties (292—295). Ethyleneamine-based imida zolines are also important intermediates for surfactants used in shampoos by virtue of their mildness and good foaming characteristics. 2- Alkyl imidazolines made from DETA or monoethoxylated EDA and fatty acids or their methyl esters are the principal commercial intermediates (296—298). They are converted into shampoo surfactants commonly by reaction with one or two moles of sodium chloroacetate to yield amphoteric surfactants (299—301). The ease with which the imidazoline intermediates are hydrolyzed leads to arnidoamine-type stmctures when these derivatives are prepared under aqueous alkaline conditions. However, reaction of the imidazoline under anhydrous conditions with acryflc acid [79-10-7] to make salt-free, amphoteric products, leaves the imidazoline stmcture essentially intact. Certain polyamine derivatives also function as water-in-oil or od-in-water emulsifiers. These include the products of a reaction between DETA, TETA, or TEPA and fatty acids (302) or oxidized hydrocarbon wax (303). The amidoamine made from lauric acid [143-07-7] and DETA mono- and bis(2-ethylhexyl) phosphate is a very effective water-in-od emulsifier (304). 

ANEDCO AC-163 is an Amino Ethyl Alkyl Imidazoline Concentrate Suggested Uses ... 

LONZA, INC. Tertiary Amines Alkyl Imidazoline Amines ... 

Amino ethyl alkyl imidazoline ANEDCO Anedco... 

Another class of amphoteric are the N-alkyl amino propionates having the structure R-NHCH2CH2COOH. The NH group is reactive and can react with another acid molecule (e.g., acrylic) to form an amino dipropionate R-N(CH2CH2COOH)2. An alkyl imidazoline-based product can also be produced by reacting alkyl imidozo-line with a chloro acid, but the imidazoHne ring will break down during formation of the amphoteric. 

In the selection of an appropriate corrosion inhibitor, an important consideration is the problem of adverse competition with other additives designed to adsorb on the liquid-metal interface. Extreme pressure and/or antiwear agents compete for the same sites as the corrosion inhibitor. Eatty amines are good corrosion inhibitors in this type of environment. However, their adverse effect on the performance of ZDDP additives often prohibits their use. Half esters or amides of dodecylsuccinic acid, phosphate esters or thiophosphates are frequently employed. A combination of inhibitors is sometimes used, for example, fatty carboxylic acids or the dimer/trimer analogues of the unsaturated acids, e.g. oleic, used in conjunction with an amine such as an ethanolamine or alkyl amine, or amide such as alkyl imidazoline and sarcosines, Eig. 6.7. Shorter chain carboxylic acid and amines are used as volatile corrosion inhibitors. 

Yelvamine. [Rhone-Poulenc/Textile Rubber] Alkyl imidazoline deriv. softener fw hair rinses, leather, textiles. 

Chem. Descrip. Hydroxyethyl alkyl imidazoline Uses Adhesion promoter in solv.-based paints and varnishes dispersant wetting agent foaming agent corrosion inhibitor in min. oils and soivs., aq. systems friction modifier in automatic transmission fluids Properties Gardner 15 max. clear Iiq. sol. in ethanol, xylene, trichloroethylene, wh. spirit, paraffin oil, and dilute sulfuric, hydrochloric, phosphoric and acetic acids disp. in water m.w. 360 dens. 930 kg/m vise. 300 mPa-s- pour pt. 3 C clear pt. 28 C flash pt. > 100 C pH 10-11 (1% aq.) surf. tens. 28 mN/m (0.1%) Draves wetting 250 s (0.1%) Ross-Miies foam 180 mm (initial, 0.05%, 50 C) cationic 90% act. 

Chem. Descrip. 1-Hydroxyethyl 2-alkyl imidazoline Uses Surfactant, wetting agent, emulsifier, detergent, thickener, corrosion inhibitor, antistat for agric. emulsions, industrial cleaners, paints/ coatings, plastics, and petroleum applies. 

Nearly all hair care products incorporate one or more cationic conditioning agents, where the latter can be either cationic surfactants or cationic polymers. The cationic surfactants can be further divided into four major classes, i.e. alkylamines, ethoxylated amines, alkyl imidazolines, and quaternaries. The quaternaries are the most widely used in the personal care industry because of their strong affinity to the hair fibre surface. 

The synthesis of these surfactants involves several steps. The first step is the preparation of a substituted imidazoline, usually l-(hydroxyethyl)-2-alkyl imidazoline, starting from fatty acids or fatty acid methyl esters and aminoethylethanolamine (AEEA) (Figure 15.15). For the production of betaines, the choice of fatty material is in most cases hydrogenated coco fatty acid. The distribution composition of fatty acid chain lengths, given above in Table 15.2, is typical also for cocoam-phoacetates. 

The process is outlined in Figure 6.7 it is based on the thermal decomposition of indene carboxylic acids in the presence of amines such as monazolines, a range of commercially available detergents (l-hydroxyethyl-2-alkyl-imidazolines). 

Carboxy amphoteric surfactants based on fatty alkyl imidazolines (imidazolinium surfactants) make up a large part of the amphoteric surfactants. Materials of this surfactant class are based on the imidazolines obtained by the condensation of fatty acids or their esters with aminoethyl ethanol amine. 

Imidazolinium betaines were initially described by Mannheimer, who obtained them from the reaction of fatty alkyl imidazolines with sodium chloroacetate [30,31]. 

Carboxyamphoteric surfactants based on fatty alkyl imidazolines ( imidazolinium surfactants) make up a large part of the amphoteric surfactants. The very divergent interpretation of their chemical structure is partly attributable to little-developed analytical procedures in the past, but is also a consequence of special processing methods by different manufacturers. Materials of this surfactant class are based on the imidazolines obtained by the condensation of fatty acids, or their esters, with AEEA. In Figures 12.4 and 12.5, a summary of the synthesis of amphoteric surfactants based on imidazolines [4,8] is presented. 

Imidazolinium betaines were initially obtained from the reaction of fatty alkyl imidazolines with sodium chloroacetate [10,11]. Their preparation in this manner, however, is not practiced. They can be prepared by the reaction of imidazoline with acrylic acid (Figure 12.11). The corresponding carboxyl ethyl betaine may be obtained, in —65% yield, by the electrophilic addition of acrylic acid on tertiary amine [35] (Figure 12.12). 

Nitrogen derivatives can be made directly from fatty acids and esters by reaction with polyamines and alcoholamines. Reaction of fatty acids with polyamines such as diethylenetriamine or aminoethylethanolamine leads to the formation of amidoamines, which can be cyclized through further condensation to give alkyl imidazolines [12-15]. Condensation with dimethylaminopropylamine affords alkylamidodimethylaminopropy-lamines, which are popular precursors to betaines and amine oxides (Figure 2.2). While imidazolines and amidoamine derivatives have lost ground to esterquats in fabric... 

Cation SF-10 [Sanyo Chem. Ind.j Chem. Descrip. Alkyl imidazoline type quat. compd. 

Chem. Descrip. 1-Hydroxyethyl 2-alkyl imidazoline Ionic Nature Cationic... 

Chem. Descrip. Methyl alkyl imidazoline sodium salt Ionic Nature Amphoteric CAS 7098343-6... 

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