Preservatives quaternary ammonium salts

Recently, there has been much interest in developing water-soluble tributyltin biocides to lessen the costs of application, and to prevent fire hazards when treating material in confined spaces. Bis(tributyltin) oxide itself has a very low aqueous solubility ( 0.001%), but it may be made water-dispersible by the addition of certain (534, 535) quaternary ammonium salts. Formulations of this type, although currently under development as wood preservatives (534), have been used extensively in the United Kingdom for the treatment of stonework to eradicate fungal growths, algae, mosses, and lichens (535). 

Fig. 10.8 A where the R substituents are alkyl or heterocyclic radicals to give compounds such as cetyltrimethylammonium bromide (cetrimide), cetylpyridinium chloride and benzalkonium chloride. Inspection of the stmctures of these compounds (Fig. 10.8B) indicates the requirement for good antimicrobial activily of having a chain length in the range Cg to Cig in at least one of the R substituents. In the pyridinium compounds (Fig. 10.8C) three of the four covalent links may be satisfied by the nitrogen in a pyridine ring. Polymeric quaternary ammonium salts such as polyquatemium 1 are finding increasing use as preservatives.

Mousses are designed for hair styling and setting hair in position. Commonly, formulations are based on cationic conditioning polymers with quaternary ammonium salts, alcohols, perfumes, colorants, water, and preservatives. They may be in propellant, foam, or jelly form for direct application to hair after shampoo or cutting, see also Fibrous Protein Formulation Chemistry Proteins. 

Biocidal applications. The use of quaternary ammonium salts in disinfecting systems for household and industrial cleaners has been known for many years [95, 96]. Alkyl-benzyldimethyl quaternaries, alkyltrimethyl quaternaries, and dialkyldimethyl quaternaries are the more commonly used biocidal quaternary ammonium salts [16]. Recently, dialkyldimethyl quaternary ammonium salts have received renewed attention as potential wood preservatives to replace the heavy metal types [97]. Metal-free wood preservative formulations containing dialkyldimethyl ammonium salts with non-halide anions, such as carboxylates, borates, and carbonates, have been developed [98, 99]. 

Some of the chemical strategies used in weatherproofing have been applied to the preservation of cellulosics for indoor storage and display. The historical Wasa sails of 1628 were preserved by copolymerizing acrylates and styrene onto this material (36). Antimicrobial treatment of cotton goods by polymerization in situ of a urea-mercury compound with formaldehyde or immersion in a quaternary ammonium salt solution protected the fabric for up to three years storage provided it did not need to be laundered (37). 

The 2002 US Presidential Green Chemistry Challenge Awards (see Box 8.3) recognized the development of a copper-based environmentally advanced wood preservative as a replacement for chromated copper arsenate. The new preservative contains a copper(II) complex and a quaternary ammonium salt. Its introduction into the market coincides with a change of policy within the wood-preserving industry arsenic-based products should have been eliminated by the end of 2003. 

Addition of vinyllithium to 441 gives 442 as a mixture of syn and anti diols. The beauty of this synthesis is that both the syn and the -diol stereoisomers rearrange to the same tetra-hydrofuran product. Thus, acetal 443 undergoes a Prins pinacol rearrangement to tetra-hydrofuran 444 upon treatment with SnCU in nitromethane. The transformation proceeds with complete preservation of enantiomeric purity. Baeyer—Villiger reaction stereospecifically introduces the 3-hydroxy substituent, and conversion to the quaternary ammonium salt completes the target molecule 446. 

Classification Quaternary ammonium salt Properties Cationic Uses Preservative in cosmetics Ceteareth... 

Benzyl dimethyl (tetradecyl) ammonium, salt with 1,2-benzisothiazol-3(2H)-one 1,1-dioxide (1 1) N,N-Dimethyl-N-tetradecyl benzenemethanaminium saccharinate Myristyl dimethyl benzyl ammonium saccharinate Quatemium-3 Classification Quaternary ammonium salt Empiricai C23H42N C7H5NO3S Uses Preservative in cosmetics Trade Name Synonyms Rewoquat QA 100 t[Goldschmidt-Rewo GmbH]... 

Synonyms N,N-Dimethyl-N-9-octadecenylbenzenemethanaminium chloride Oleyl benzyl dimethyl ammonium chloride Oleyl dimethyl benzyl ammonium chloride Classification Quaternary ammonium salt Empirical C27H48N Cl Properties M.w. 422.14 cationic Toxicology TSCA listed Uses Preservative in cosmetics conditioner, antistat for clear hair rinses conditioner in pharmaceuticals in food-pkg. adhesives Regulatory FDA 21CFR 175.105, 178.1010 Trade Name Synonyms AM M ONYX KP [Stepan http //www.stepan.com], AM MONYX LKP t[Stepan http //www.stepan.com], Cycloton 7LUF t[Rhodia HPCII http //www.rhodia-hpcii.com], Empigen BCJ-50 t[Huntsman Surf. Sciences... 

Tallow trimethyl ammonium chloride. See Tallowtrimonium chloride Tallow trimethyl ammonium methosulfate. See Tallowtrimonium methosulfate Tallow trimethylene diamine. See Tallowaminopropylamine Tallowtrimonium chloride CAS 8030-78-2 7491-05-2 68002-61-9 EINECS/ELINCS 232-447-4 Synonyms Quaternary ammonium compds., tallow alkyl trimethyl, chlorides Tallow trimethyl ammonium chloride Trimethyl tallow ammonium chloride Classification Quaternary ammonium salt Formula [R-N(CH3)3]" Cr, R rep. alkyl groups derived from tallow Properties Cationic Toxicology TSCA listed Uses Antistat, preservative, surfactant in cosmetics dispersant external antistat for plastics emulsifier in corrosion inhibitor formulations for oil field brines and HCI acidizing systems textile softener, dyeing aid ... 

Surface active compounds are often effective to potentiate the activity of the microbiddes. It is observed that the lower the content of volatile organic carbon in a paint the more important is the formulation of a preservative to transport the active ingredient to the location within the multiphase system where it is needed. Frequently, an optimum balance of membrane-activity and reactivity of the second active ingredient against microorganisms in complex matrices has to be found. It can be demonstrated that surface active compounds [II, 18.] like e.g. quaternary ammonium salts, fatty amine derivatives, ethoxylated alcohols or dodecylbenzene sulfonic add potentiates the activity of bactericides like BIT, MIT. 

Emulsions often contain additives that are subject to biodegradation. The destruction of biodegradable stabilizers and rheology modifiers will lead to degradation of performance properties at best and complete destabilization of the emulsion at worst. Sometimes emulsifiers with biocidal properties such those based on quaternary ammonium salts can be used in the formulations. If that is not possible, then a small amount of biocide may be required to preserve the integrity of the emulsion. When oxidative degradation is an issue, then antioxidants will also have to be part of the formulation. 

Classification Polymeric quaternary ammonium salt Uses Antistat, film-former in cosmetics, pharmaceuticals preservative in soft lens prods. 

Commonly used preservative agents include organic acids such as benzoic acid and salts, the parabens, (alkyl esters ofp-hydroxybenzoic acid), sorbic acid and salts, phenolic compounds, quaternary ammonium compounds, alcohols, and mercurials such as thimerosal in 0.001-0.004% concentration. 

The antimicrobial efficacy of the amine-formaldehyde reaction products essentially corresponds to the formaldehyde content of these compounds. Known exceptions are HTA, hexahydro-oxadiazines and octahydro-s-tetrazines, which derive from ammonia respectively certain alkylolhydrazines (Paulus, 1980) here the detection of formaldehyde by the Taimenbaum methods gives a negative result, which means that these substances have no significant antimicrobial effect at neutral to alkaline pH they release formaldehyde in acidic media only. This pH dependency is broken off, if, for example, HTA is quatemized (Jacobs et al., 1916). In contrast to HTA the quaternary hexaminium salts release formaldehyde widely independent of pH and therefore may be used as preservatives also for media of neutral to alkaline pH. They are not comparable with the surface active conventional quaternary ammonium compounds (QACs see Section 16.1)... 

Creosote and chromated copper arsenate (CCA) have been widely used as preservatives for antibacterial treatment of wood. In spite of their excellence in this property, they have some drawbacks in toxicity. Therefore, less toxic and environmentally-benign chemicals are expected to be used. Quaternary alkylammonium salts are, thus, one of the candidates for the anti-microbial treatment of wood. In this study of wood-inorganic composites, trimethoxysilylpropyldimethyloctadecyl ammonium chloride (TMSAC), shown below, was used as a property enhancer to add an anti-bacterial property to wood (Tanno, 1997). 

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