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  Diethyl methyl ammonium nitriles and detergents and cleaning agents containing said ammonium nitrilesRelated Patent Categories: Bleaching And Dyeing; Fluid Treatment And Chemical Modification Of Textiles And Fibers, Bleaching, Chemical, Sulfur CompoundsThe Patent Description & Claims data below is from USPTO Patent Application 20070245498. Brief Patent Description - Full Patent Description - Patent Application Claims
[0001] This invention relates to odor-neutral short-chain ammonionitriles, to their granules and to their use for enhancing the bleaching action of peroxygen compounds in the bleaching of colored stains both on textiles and on hard surfaces, and to washing and cleaning compositions which comprise these nitriles as bleach activators. [0002] Inorganic peroxygen compounds, especially hydrogen peroxide and solid peroxygen compounds which dissolve in water to release hydrogen peroxide, such as sodium perborate and sodium carbonate perhydrate, have been used for some time as oxidizing agents for disinfection and bleaching purposes. The oxidizing action of these substances depends greatly upon the temperature in dilute solutions; for example, sufficiently rapid bleaching of soiled textiles is achieved with hydrogen peroxide or perborate in alkaline bleaching liquors only at temperatures above about 80.degree. C. [0003] It is known that the oxidative action of peroxidic bleaches, such as perborates, percarbonates, persilicates and perphosphates, at low temperatures can be improved by adding precursors of bleaching peroxy acids, known as bleach activators. According to the prior art, many substances are known to be bleach activators. They are usually reactive organic compounds having an O-acyl or N-acyl group, which form the corresponding peroxy acids in alkaline solution together with a source for hydrogen peroxide. [0004] Representative examples of bleach activators are, for instance, N,N,N',N'-tetraacetylethylenediamine (TAED), glucose pentaacetate (GPA), xylose tetraacetate (TAX), sodium 4-benzoyloxybenzenesulfonate (SBOBS), sodium trimethylhexanoyloxybenzenesulfonate (STHOBS), tetraacetylglycoluril (TAGU), 1-phenyl-3-acetylhydantoin (PAH), sodium nonanoyloxybenzenesulfonate (NOBS) and sodium isononanoyloxy-benzenesulfonate (ISONOBS). An interesting group is that of cationic compounds which contain a quaternary ammonium group, since they are highly effective bleach activators. [0005] As a result of addition of these activators to an aqueous peroxide solution, perhydrolysis takes place with release of an organic peracid. This enhances the bleaching action of the solutions to such an extent that, even at temperatures between 40 and 60.degree. C., they have essentially the same effects as a peroxide solution alone at 95.degree. C. [0006] A major disadvantage of the bleaching activators mentioned is that they usually leave behind bulky leaving groups (for example phenolsulfonates) on completion of perhydrolysis, which are of no significance whatsoever for the bleaching process. [0007] From an ecological point of view, bleaching activators in which a highly reactive peracid but no leaving group is released in the perhydrolysis step are therefore of interest. This is achieved, for example, by a cyano group. This probably forms a peroxyimide acid in the perhydrolysis, which then acts as the bleaching agent. [0008] Examples thereof are ammonionitriles, characterized by the structural element [0009] Compounds of this type and their use as activators in bleaches are described in EP-A-303 520, EP-A-458 396 and EP-A-464 880. Ammonionitriles where two of the R.sup.1, R.sup.2 or R.sup.3 groups are a long-chain alkyl group are claimed in WO 03/078561. [0010] However, low molecular weight ammonionitriles having a total of not more than 12 carbon atoms are of particular interest, since they have excellent water solubility, are highly reactive and are simultaneously particularly weight-effective. The latter plays a particular role in volume-effective washing compositions with low dosage. There has therefore been no lack of attempts in the past to prepare such compounds. Numerous patent applications therefore describe the use of trimethylammonioacetonitriles of the formula where X.sup.- is an anion, for example chloride, sulfate, hydrogensulfate, methylsulfonate, ethanesulfonate, toluenesulfonate, benzenesulfonate or cumenesulfonate. Examples of the synthesis, granulation and use of these trimethylammonioacetonitriles can be found in WO 02/012175, WO 02/012427, DE 100 38 844 or EP 13 12 665. [0011] A serious disadvantage of all trimethylammonioacetonitriles is, however, that they release, under alkaline conditions, whether they be in the wash liquor or in the course of prolonged storage in an alkaline washing composition, traces of trimethylamine and hence a fishy odor which makes their use in the household sector impossible. There has therefore been no lack of attempts to prepare odor-free trimethylammonioacetonitriles, for example by exchange of the anion or by deodorization, as described in DE 102 24 509. [0012] Surprisingly, even the higher homolog (dimethylethylammonioacetonitrile tosylate) releases traces of trimethylamine under alkaline conditions. As a result of alkaline treatment, traces of trimethylamine can be detected even from N-methylmorpholinioacetonitrile methosulfate. The mechanism of the formation is unclear, but one of the methyl groups bonded to a nitrogen atom is probably transferred to ammonia which is released as a result of hydrolysis of the nitrile. Repeated methyl group transfer then forms traces of trimethylamine. [0013] It has now been found that, surprisingly, N-methylammonionitriles of the above-described type which have two ethyl substituents are effective bleach activators which do not form trimethylamine under alkaline conditions even though a methyl group resides on the nitrogen. [0014] The present invention thus provides compounds of the general formula where X.sup.- is an anion, for example chloride, bromide, sulfate, hydrogen-sulfate, methosulfonate, ethanesulfonate, toluenesulfonate, benzene-sulfonate or cumenesulfonate. Particular preference is given to the chloride, hydrogensulfate, sulfate, methosulfate and toluenesulfonate anions. [0015] The synthesis routes for the diethylmethylammonioacetonitriles of this invention will be illustrated with reference to a few general examples: [0016] 1. Diethylamine is initially charged together with a base, preferably alkali metal carbonate or alkali metal hydroxide, in a solvent, preferably in absolute ethanol or in a toluene/water mixture. At temperatures between 0 and 50.degree. C., preferably at from 10 to 30.degree. C., chloroacetonitrile is added dropwise. After from 1 to 50 hours of reaction time, the organic phase is removed and the aqueous phase is extracted with an organic solvent. The solvent is removed from the combined organic phases. The resulting crude product can be purified further by fractional distillation. The diethylaminoacetonitrile formed is taken up in water or an organic solvent and reacted with an alkylating agent such as methyl chloride, dimethyl sulfate or methyl p-toluenesulfonate at temperatures between 20 and 100.degree. C. to give the corresponding N-cyanomethylammonium salt. The salt can be obtained by conventional methods of workup, such as extraction, crystallization, suction filtration, washing of the crystal slurry on the suction filter and drying. It is possible to proceed analogously from ethylmethylamine, in which case the quaternization is performed with an ethyl derivative. [0017] 2. Diethylmethylamine and chloroacetonitrile are reacted in a suitable solvent, for example in acetone, at temperatures between 10 and 70.degree. C. for from 1 to 12 hours. The precipitate formed, the N-cyano-methylammonium chloride, is filtered off, washed with an organic solvent and dried. [0018] 3. Diethylamine, sodium cyanide and an aldehyde or a ketone, preferably formaldehyde in the form of a 36% formalin solution, are combined in a solvent, preferably an ethanol/water mixture or water. [0019] After a reaction time of from 1 to 12 hours at temperatures between 10 and 80.degree. C., preferably at from 10 to 30.degree. C., aqueous hydrochloric acid is added to the mixture. The aqueous phase is extracted with a suitable organic solvent, for example methylene chloride or diethyl ether. After drying over magnesium sulfate, the solvent is removed from the combined organic phases. The resulting crude product can be purified further by fractional distillation. The dialkylamino-acetonitrile formed is taken up in an organic solvent and reacted with an alkylating agent such as methyl chloride, dimethyl sulfate or alkyl arylsulfonate at temperatures between 20 and 100.degree. C. to give the corresponding N-cyanomethylammonium salt. The salt can be obtained by conventional methods of workup, such as extraction, crystallization, suction filtration, washing of the crystal slurry on the suction filter and drying. It is possible to proceed analogously from ethylmethylamine, in which case the quaternization is performed with an ethyl derivative. [0020] The invention also provides for the use of these ammonionitriles as bleach activators in bleaching washing and cleaning compositions. In a particular embodiment, the inventive diethylmethylammonioacetonitrile is used in the form of a granule in washing and cleaning compositions. Such granules may contain from 5 to 95% by weight, but preferably from 20 to 90% by weight, of the inventive diethylmethylammonioacetonitrile. As further constituents, such a granule may comprise a further bleach activator. Preference is given here to decanoyloxybenzoic acid, sodium nonanoyloxybenzenesulfonate, tetraacetylethylenediamine or 1,5-diacetyl-2,4-dioxo-1,3,5-hexahydrotriazine. In addition, granulating aids and/or coating materials may be employed for the formation of the granule. [0021] The term "bleaches" here is understood to mean both the bleaching of soil on the textile surface and the bleaching of soil in the wash liquor which has been detached from the textile surface. For the bleaching of stains on hard surfaces, the same applies mutatis mutandis. Further potential applications are within the personal care sector, for example in the bleaching of hair and for the improvement in the effectiveness of denture-cleaning compositions. In addition, the inventive complexes find use in commercial laundries, in wood- and paper-bleaching, the bleaching of cotton and in disinfectants. [0022] The invention further relates to a process for cleaning textiles and also hard surfaces, especially of dishwave, using the cationic nitriles mentioned in aqueous solution optionally comprising further washing composition or cleaning composition constituents, in particular peroxygen-based oxidizing agents, and also to washing or cleaning compositions for hard surfaces, especially cleaning compositions for dishes, preference being given to those for use in machine processes, which comprise such cationic nitriles. [0023] The inventive use consists substantially in creating conditions in the presence of hard surfaces contaminated with colored stains or of a correspondingly soiled textile, under which a peroxidic oxidizing agent and the cationic nitrile can react with one another, with the aim of obtaining more strongly oxidizing conversion products. Such conditions are present especially when the reaction partners meet one another in aqueous solution. This can be done by separately adding the peroxygen compound and the cationic nitrile to a solution optionally containing washing or cleaning composition. However, the process according to the invention becomes particularly advantageous with the use of a washing composition or cleaning composition for hard surfaces, which comprises the cationic nitrites and optionally a peroxygen-containing oxidizing agent. The peroxygen compound may also be added to the solution separately in substance or as a preferably aqueous solution or suspension when a peroxygen-free washing or cleaning composition is used. [0024] The inventive washing and cleaning compositions, which may be present in the form of granules, pulverulent or tableted solids, in the form of other shaped bodies, homogeneous solutions or suspensions, may, apart from the bleach-boosting active ingredient mentioned and a peroxygen compound, in principle comprise all known ingredients which are customary in such compositions. The inventive compositions may in particular comprise builder substances, surfactants, peroxygen compounds, additional peroxygen activators or organic peracids, water-miscible organic solvents, sequestrants, thickeners, preservatives, pearlescents, emulsifiers and enzymes, and also special additives having color care or fiber care action. Further assistants such as electrolytes, pH regulators, silver corrosion inhibitors, foam regulators and colorants and fragrances are possible. Continue reading... Full patent description for Diethyl methyl ammonium nitriles and detergents and cleaning agents containing said ammonium nitriles Brief Patent Description - Full Patent Description - Patent Application Claims Click on the above for other options relating to this Diethyl methyl ammonium nitriles and detergents and cleaning agents containing said ammonium nitriles patent application. ###  How KEYWORD MONITOR works... a FREE service from FreshPatents1. Sign up (takes 30 seconds). 2. Fill in the keywords to be monitored. 3. Each week you receive an email with patent applications related to your keywords. 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