Sarcosinate surfactants

Dishwasher Rinse Aids are formulated from the Hamposyl sarco-sinates and low-foam nonionics. The sarcosinate surfactant raises the cloud point and solubility of the nonionic and increases wetting action without contributing added foam. 

N,N-Dimethyl-N-tallow-N-(3-sulfopropyl)-ammonium betaine N,N-Distearyl-N-methyl-N-(3-sulfopropyl)-ammonium betaine surfactant, biotechnology Stearoyl sarcosine surfactant, bleaches Lauramine oxide surfactant, body care... 

Tetraethylammonium perfluorooctyl sulfonate surfactant, fabric detergents Oleoyl sarcosine surfactant, fabric softeners Disodium distyrylbiphenyl disulfonate Myristamine oxide PEG-8 isostearate Stearamine oxide surfactant, fabrics... 

PEG-4 dioleate PEG-150 distearate PEG-40 hydrogenated castor oil PEG-60 hydrogenated castor oil PEG-100 hydrogenated castor oil PEG-75 oleate PEG-150 oleate Poloxamer 237 Polysorbate 20 Polysorbate 65 Polysorbate 85 Propylene glycol laurate Propylene glycol palmitate Sodium diphenyl ether disulfonate Stearoyl sarcosine surfactant, metalworking compounds Laureth-3... 

Sarcosinate surfactants are derived from natural fatty acids and an amino acid, sarcosine (A -methyl glycine). Typically the sarcosinate is used in the form of its sodium, potassium, or ammonium salt solution. A -Acyl sarcosinates are produced commercially by the Schotten-Baumann reaction of the sodium salt of sarcosine with the appropriate fatty acid chloride under carefully controlled conditions. The commercially available sarcosinate surfactants are cocoyl sarcosine, lauroyl sarcosine, myristoyl sarcosine, oleoyl sarcosine, stearoyl sarcosine, sodium cocoyl sarcosinate, sodium lauroyl sarcosinate, sodium myristoyl sarcosinate, ammonium lauroyl sarcosinate, TEA lauroyl sarcosinate, ammonium cocoyl sarcosinate, monoethanolamine cocoyl sarcosinate, and TEA oleoyl cocoyl sarcosinate. 

Sarcosinate surfactants have been widely used in personal wash, skin care, and hair care formulations as coactives. They are particularly useful in providing a rich, stable lather, especially in the presence of sebum. Lathers produced from other anionic and amphoteric surfactants are remarkably enhanced by the addition of sarcosinates. Maximum foaming and detergency are developed in the pH range 4-8. The adsorption of sarcosinates onto the hair results in manageability and reduced static buildup. Sarcosinate surfactants are easily... 

Results forthcoming from the literature do not always assist in building a picture of events. The observation [65] that 2- and 4-hydroxylation of biphenyl was competitively inhibited by polysorbate 80 in the hamster contrasts with the finding that in the rat, polysorbate 80 (2mM) had no effect on the linear microsomal demethylation of aminopyrine (also a Type V substrate) [66]. The question arises whether surfactants such as polysorbate 80 produce their effects by interaction as an alternative substrate or by perturbation of a membrane bound enzyme system. Commercial samples of polysorbate 80, Brij 35 and Triton X-100 all enhance the activity of a sarcosine dehydrogenase isolated from a strain of Pseudomonas, due to the presence of free oleic acid in these non-ionic surfactants. Deoxycholate and a sarcosine surfactant (N-dodecanoyl N-methyl glycine) inhibit activity [67]. Correlations between the CMC of the non-ionic surfactants and the concentrations required for enzyme activation are seen in Table 10.9. 

Levenol C-201 Levenol C-301 surfactant, extrusion Chemstat 182 Chemstat 192NCP Chemstat 273-E surfactant, eye care Jordapon ACI-30 G surfactant, eye creams Hetblend SE-100 surfactant, fabric care Rhodaterge 559L surfactant, fabric cleaners Stanfax 969 Stanfax 1045 surfactant, fabric detergents Alfonio 1618-5 Oleoyl sarcosine surfactant, fabric dyeing Isotao NC... 

Surfa.cta.nts, Ai-Acylglutamates, sodium A/-lauroyl sarcosinate [137-16-6] and A/-acyl-alanine Na salt are used in the cosmetic field as nontoxic surfactants (237). Some of them (eg, A/-acylglutamic acid dibutylamide) are used as oil geUating agents to recover efduent oil in seas and rivers (238). 

The surfactant most commonly used is the anionic detergent sodium lauryl sulfate. Other surfactants that have been used include sodium dodecylbenzene sulfonate [25155-30-0] sodium A/-lauroyl sarcosinate or Gardol [137-16-6] and sodium cocomonoglyceride sulfonate [3694-90-4]. Cationic and nonionic surfactants are not used for several reasons, including incompatibiUty with the abrasive system and lack of high foaming capabiUty. 

Sodium lauryl sarcosinate is very similar to the lauryl sulfate class of detergents and surfactants. The sulfate group is replaced with the amino acid sarcosinic acid, and the ammonium group is replaced with a sodium atom. The result is a detergent that is milder on the skin and oral membranes, and can be used in toothpastes without causing irritation of the gums. 

Ong et al. [134] found that several hydrophilic anionic, non ionic, or cationic surfactants can alleviate the deleterious effect of magnesium stearate over-mixing on dissolution from capsules when added with the lubricant in a ratio as low as 1 5 (w/w). These successful surfactants were sodium A-lauroyl sarcosinate, sodium stearoyl-2-lactylate, sodium stearate, polox-amer 188, cetylpyridinium chloride, and sodium lauryl sulfate. The lipophilic surfactant glyceryl monostearate did not alleviate the magnesium stearate mixing effect. A reduction in thier particle size was shown to enhance effectiveness, particularly in the case of surfactants with low solubility and slow dissolution rate. 

Similarly, acylamino acids can be prepared with 100% atom utilization via palladium-catalyzed amidocarbonylation. " The method was used for the synthesis of a surfactant from sarcosine (Figure 9.8). 

TVAcylsarcosinates. Sodium IV-lauroylsarcosinate [7631-98-3] is a good soap-like surfactant. Table 4 gives trade names and properties. The amido group in the hydrophobe chain lessens the interaction with hardness ions. N-Acylosarcosinates have been used in dentifrices (qv) where they are claimed to inactivate enzymes that convert glucose to lactic acid in the mouth (57). They are prepared from a fatty acid chloride and sarcosine ... 

Because the sarcosinates have the ability to raise the cloud point of nonionic surfactants, this feature can be used to advantage in the formulation of dishwasher rinse aids. At the cloud point and up to 15C above it, foam generation is reduced and detergency is enhanced. By adjusting the cloud point of the formula to the use temperature, one can take full advantage of this performance feature. 

Fatty Acid—Sarcosine Condensates. These surfactants are prepared by the reaction of fatty acid chlorides with methyl glycine sodium lauroyl sarcosinate [137-16-6] is an example of this group. They are most effective at pH 5.5—6.0 for foaming activity in soft to moderately hard water. The action of these deteigents is gready reduced under severe hard water conditions. The sarcosinates exhibit compatibility with cationic surfactants and have been suggested for use in formulation of conditioning shampoos (7). 

N-Acylsarcosinates. Sodium AMauroylsarcosinatc is a good soaplike surfactant. The amido group in the hydrophobe chain lessens the interaction with hardness ions. A-Acylosarcosinates are prepared from a fatty acid chloride and sarcosine. 

Ci2 i4 olefin sulphonates are also used in personal care formulations since they are less aggressive than LAS and will not over-strip (i.e. degrease to leave an excessively dry or squeaky feel) the skin or hair although some care maybe required in formulating to compensate for a dry feel to the foam. AOS-based formulations are also more difficult to thicken than products based on alkyl sulphates or alkyl ether sulphates but use of alkanolamides or sarcosinates as secondary surfactants can overcome both problems and give a product more acceptable to the consumer. 

Salt is a by-product. Due to the stability of the amide group, the free acid can be formed and separated from the reaction mixture to give a salt-free product. The stability of the amide group also allows sarcosinates to be used in a wider range of chemical environments than isethionates (see below). Sarcosinates are stable under moderately acidic conditions but will degrade at low pH or with elevated temperature. The surfactants are moderately soluble at high pH and the sodium salts are supplied as a 30% solution. 

Applications. Sarcosinates show low irritation potential and are good foamers. Due to these properties they find applications in personal care products where synergistic effects with other surfactants may also be exploited. In combination with other anionics, sarcosinates will often detoxify the formulation and give improved foaming and skin feel. Sarcosinates are also used for their hydrotropic properties - the addition of sarcosinate to other anionics often gives a reduced Kraft point or a raised cloud point if combined with non-ionic surfactants. Lauroyl sarcosinate is used to formulate SLS-free toothpastes which are claimed to have improved taste profile. 

Sodium lauroyl sarcosine Sodium dioctyl sulfosuccinate Alkylarylsulfonate Sodium dodecyl sulfate9 Cationic surfactants... 

The encapsulation of magnetite particles into polystyrene particles was efficiently achieved by a miniemulsion process using oleoyl sarcosine acid [ 109] or the more efficient oleic acid as first surfactant system to handle the interface magnetite/styrene, and SDS to stabilize the interface styrene/water, thus creating a polymer-coated ferrofluid (Fig. 15b). Since the magnetite particles were very small (ca. 10 nm), each polymer particle was able to incorporate many inorganic nanoparticles. A content of 20 wt% could be incorporated in this way. 

America s Du Pont and 3M and Japan s Sanyo pay particular attention to the development of fluorine-based surfactants. Air Products with its acetylene derivatives Surfynol and W. R. Grace with its sarcosinates (Hampshire Chemicals) have also focused on well-defined segments of the business. With world demand exceeding two million tons, the market of surfactants for industry is of a nature to attract a large number of operators, raw material suppliers, processors of these raw materials into anionic, nonionic, and cationic derivatives, or downstream industries that use surfactants in various formulations. 

Sarcosinate specialty surfactants are currently made by acylation of naturally occurring amino acids with an acyl chloride. The use of a secondary amide for amidocarbonylation has been reported to give poor yields of amido acid since the corresponding oxazolone intermediate cannot be formed. Lin has demonstrated, however, that the amidocarbonylation of A-methylamine gives excellent yields of A-acyl sarcosinates (eq. (11)) when conducted in the presence of dicobalt octacarbonyl at 120°C with CO/H2 = 3 1. Sarcosinate selectivity is typically 95 %, at 92 % A-methylamine conversion. 

Use Surfactant, polymerization initiator, antienzyme agent, foamer synthesis of lauroyl peroxide, sodium A-lauroyl sarcosinate, and other sarcosi-nates. 

VanseaL. T. Vanderbilt] Sarcosinesor sarcosinates industrial surfactants, chelating agents for soaps, bath gels, shanq>oos, shaving creams, dentifiices, textile and leather processing. 

AI3-52409 Dodecanoic acid, chloride Dodecanoyl chlori.de n-Dodecanoyl chloride EINECS 203-941-7 HSDB 5567 Laurie xid chloride Lauroyl chloride. Surfactant, polymerization initiator, antienzyme agent, foamer synthesis of lauroyl peroxide, sodium lauroyl sarcosinate, other sarcosinates. Liquid mp = -17 bpis = 145 d = 0.9169 very soluble in Et20. Degussa-HIlls Corp. Elf Atochem N. Am. PPG Ind. 

The more complex Lamepon and Igepon type of amides, including the sarcosine (iV-methj lycine) [107-97-1] and A/-methyl taurine (AJ-methylarmno-ethanesulfonate) types shown in Table 4, are used primarily as specialty surfactants in shampoo and toothpaste formulations. These rather complex stmctures have limited use in very specialized applications. 

Acylated amino acids are known as anionic surfactants for a long time. Besides ether carboxylates mentioned above, sarcosinates (N-methylgycinates) is the most known type of mild "cryptoanionic" surfactants synthesised by direct reaction between saturated or unsaturated fatty acid halides and sarcosine in aqueous alkali [10, 11,74] ... 

A convenient source of sodium sarcosinate is sodium chloroacetate and methylamine. Before the 2" World War sarcosinates have been known as Medialan , useful as textile chemicals with recognised lesser sensitivity (as compared to soaps) to hydrolysis, compatibility with other surfactants, and higher stability in hard water. Some antistatic, lime soap dispersing, bacteriostatic and corrosion-preventive properties are other useful properties of sarcosinates. Sodium N-lauroyl sarcosinate show moderate compatibility with a range of cationic... 

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