DE3724900A1 - N-ALKYLNEOALKANAMIDES AND THE PREPARATIONS THEREOF - Google Patents

Abstract

N-lower alkyl neoalkanamides of 1 to 4 carbon atoms in the lower alkyl thereof, and of 5 to 14 carbon atoms in the neoalkanoyl group, e.g. N-methyl- and N-ethyl neodecanamides, are new compounds which have pestrepellent properties, being especially effective against insects such as cockroaches. They may be applied directly to surfaces to be treated or they may be incorporated in detergent compositions, such as laundry detergents, floor and wall cleaners, rug cleaners and shampoos, hair shampoos, and liquid and bar soaps, and have been found to be sufficiently substantive to the substrate being washed so as to impart insect repelling properties to it. In addition to insect repelling uses, the N-lower alkyl neoalkanamides are also useful components of perfumes.

Description

The invention relates to N-alkylneoalkanamides, which are new chemical compounds and insect repellent Have properties and as ingredients for perfumes are suitable. The invention relates in particular N-lower alkylneoalkanamides, especially N-methyl and N-ethyl-neodecanamides and neotridecanamides, which are particularly effective against insects such as cockroaches, if they hit the surfaces of objects to be protected or applied by areas. The The invention further relates to a wide variety of compositions and agents containing such N-alkylneoalkanamides, these compositions Can be perfumes or insect repellants, which, according to use, repel the active compounds to the insects deposit surfaces to be made.

Known insect repellants are toxic, others have an unpleasant smell or cause discoloration, so that their use is limited. Most known insect repellents are tertiary Amides, of which the N, N-diethyl-m-toluolamide, too Called "DEET", considered the most effective so far has been and is suitable for practically all purposes is.

The neoalkanamides according to the invention and in particular the N-methylneodecanamide and N-methylneotridecanamide are superior to DEET in terms of long-term effects. In addition, the neoalkanamides are in their repellent Property also against other insects like mosquitoes effective and show a much greater effectiveness towards Anopheles quadrimaculatus as DEET.  

The N-alkylneoalkanamides according to the invention which are used for Repelling insects used have alkyl residues with 1 to 4 carbon atoms, while the neoalkanoyl group 7 to 14 or 16 carbon atoms and preferably has 9 to 11 or 13 carbon atoms. Methylneodecanamide, which is particularly preferred is effective against cockroaches.

The invention further relates to particulate or liquid detergent compositions, shampoos for Carpets and upholstery, hair shampoos, detergents for hard surfaces, bar-like soaps and detergents containing N-alkylneoalkanamide as well as solutions and dispersions of the neoalkanamides in a liquid medium or dispersions in a particulate or powdery carrier to them on the areas to be protected. The invention also relates to methods of repelling insects by applying the neoalkanamides to the surface the objects or areas to be protected or near it. The insect repellants according to the invention Agents can also use insecticides used to keep the insects out of an area to expel and in the direction of insecticides too to lead. They can also be formulated with insecticides be so that after loss of the insect repellent Properties of the treated areas are still are insect-proof.

The perfumes according to the invention containing such N-Lower alkylneoalkanamides contain one or more lower alkylneoalkanamides with 1 to 4 carbon atoms in the lower alkyl radical and 5 to 14 carbon atoms in the neoalkanoyl group and at least one perfume component, selected from the group of ethereal  Oils, esters, ethers, aldehydes, alcohols, hydrocarbons, Ketones and lactones, the content of which Neoalkanamides in a range from 0.1 to 98% by weight lies.

Computer and hand research in the prior art have given no evidence that volatile primary and secondary amides as perfume or insect repellent Components are known; it was rather found that N-lower alkylneoalkanamides according to Invention are new and not obvious.

The closest prior art relates to U.S. Patent Application S.N. 7 16 871 of March 27, 1985 N-higher-alkylneoalkanamides, which, however, act as antistatic agents, but not because of their insect repellent Properties are used.

The alkylneoalkanamide composition according to the invention and the methods according to the invention relate to compounds whose alkyl group is 1 to 18 and preferably 1 to 4 and especially 1 or 2 carbon atoms such as methyl or contain ethyl. The neoalkanoyl group, the derived from any suitable neoalkanoic acid can, some of which are commercially available generally 5 or 7 to 14 carbon atoms such as Neodecanoyl, Neotridecanoyl or Neoheptanoyl, where Neodecanoyl is preferred. Among those available standing neoalkanoic acids are neopentane, neoheptane Neononan, Neodecan, Neododecan, Neotridecan and Neotetradecanoic acid available; the corresponding alkyl neoalkanamides such as methyl and ethyl neoalkanamides be made from such neoalkanoic acids. Usually the alkyl radicals are straight-chain; You can also be branched. The neoalkanamides can be in pure Form are available, but can also be from the commercially available  Products with technical purity are obtained, so that the amides made from these acids as Mixtures are present.

The amides of the invention have the following general ones formula

in which R, R 'and R' 'are alkyl radicals, the Sum of carbon atoms in a range from 5 to 12 lies; R ′ ′ ′ is an alkyl radical, preferably a lower alkyl radical with preferably 1 to 4 carbon atoms.

The figures show

FIG. 1 is an infrared absorption spectrum of N-Methyldeodecanamid;

Fig. 2 is an infrared spectrum of N-Ethylneodecanamid;

Fig. 3 is an infrared spectrum of N-Methylneoheptanamid;

Fig. 4 is an infrared spectrum of Methylneotridecanamid;

Fig. 5 is a graphical representation of the insect repellent effect against the time of N-methylneodecanamide compared to DEET.

For the production of the neoalkanamides according to the invention  a neoalkanoyl chloride slowly with the corresponding primary amine in ethyl ether and the reaction mixture then with distilled water, a dilute hydrochloric acid solution, a dilute one Sodium hydroxide solution and again with water until washed neutral pH. The ether is Steam bath and then removed under vacuum. The The end product obtained is water white to light amber in color and essentially pure. Alternatively you can the neoalkanoic acid also directly with the lower alkylamine implement.

The neoalkanoic acids such as neodecane, neotridecane, neoheptane and neopentanoic acid become more suitable by reaction branched alkenes with carbon monoxide under high pressure at elevated temperature in the presence of a aqueous acid catalyst obtained after the Koch reaction. This forms the carbonium ion, which with Carbon monoxide and the catalyst to form a complex is implemented, which is then used to generate the free acid is hydrolyzed using the following formula Has

For example, the total number of neodecanoic acid is on carbon atoms in R, R ′ and R ′ ′ 8; 31% the neodecanoic acid has a structure in which R 'and R ′ ′ is methyl and R is hexyl, while 67% the material at R ′ is a methyl radical and R ′ ′ is a Has an alkyl radical with a carbon atom content, which is larger than methyl and smaller than that of R,  where R has fewer carbon atoms than hexyl, but more as R '' has; in 2% of the formula-based connection R ′ and R ′ ′ have more carbon atoms than the methyl radical and less than the radical R, where R has fewer carbon atoms has as hexyl and more than the radicals R ′ and R ′ ′. The neoalkanoic acids for the preparation of the invention Amides can contain 7 to 16 carbon atoms, such as Neoheptan, neononan, neodecane, neododecane, neotridecane and neotetradecanoic acids. If the rest R 5 or has more carbon atoms, this is alkyl branches. Those for the production of the invention N-Lower alkylneoalkanamides used as the starting product Acylchloride can be derived from neoalkanoic acids and a suitable chlorinating agent such as phosphorus trichloride or optionally thionyl chloride can be obtained.

The insect repellent compounds according to the invention can use a wide variety of materials in their manufacture be added, for example a pulp in papermaking, basic mixes Rubber or polymer plastics, flakes or Chips in the manufacture of press plates, they can also injected into the insect repellent objects or introduced in some other way. Usually become the insect repellent compounds on surfaces of areas or objects either directly, in liquid solution or dispersion, in a powdery Carrier, in a detergent or cleaning composition, in a detergent for floor and walls, as a shampoo for upholstery or carpets, as a hair shampoo, as a liquid soap, in bar soap or used in any other compositions. Suitable compositions are, for example, insecticides and bactericidal washing or immersion baths for humans or animals, furniture polishes, floor waxes and polishes,  Ointments, cream and topical medication, Insecticides, fungicides, bactericides, fertilizers, Peat and potting soil, to name a few. In In some cases you can also see the items and compositions refresh again with active alkanamide components, to renew their insect repellent effect. The preparations according to the invention are usually direct or indirectly from the outside to the areas to be treated applied and later to maintain the insect repellent Effect continuously treated. The insect repellent N-alkylneoalkanamides such as N-methylneodecanamide or N-methyltridecanamide can on the surface to be treated is painted or can by washing the same with the active ingredient containing detergents are treated. The invention Connections are liquid at normal temperature or pasty and water-insoluble so that they are made Detergents or other preparations substantively tease the surfaces even if these connections then rinsed off; after a direct or indirect application on such surfaces remains a sufficient proportion of alkanamides and repels insects. Although different application rates of the various alkanamides for effective Insect repellent for a wide variety of insects from different surfaces and under different conditions are generally possible, the active ones Ingredients in an amount of 0.002 to 100, mostly from 0.01 to 5 and preferably in an amount of 0.1 to 2 g / m², for example to drive off cockroaches used while higher deposition rates of 10 up to 100 g / m² can be used for mosquitoes.

Since the insect repellent compounds according to the invention are volatile, they become in the environment of the application center  recognized by the insects that are not just one Contact with the treated items, but also avoid their proximity. Application of drugs on the wall of a cupboard also sells cockroaches from inside the closet so the cockroaches don't turn on the dishes and the kitchen appliances. Analogue a treatment of pantries or sideboards is enough with a furniture polish that the volatile according to the invention Contains funds to keep the cockroaches from entering to deter; it is also possible to use the shelves to lay out a paper which is an insect repellent Contains neoalkanamide. Washing textiles with a detergent containing the inventive insect repellent prevents the insects, to settle on the textiles or the carrier of these and stab the latter. Treating a Carpets with a carpet shampoo or detergent for floor coverings with the compounds according to the invention prevents insects from entering the rooms and nesting or egg laying in or under the Carpet. Washing floors and walls with a cleaning agent containing insect-repellent active ingredients causes the deposition of the invention insect repellent and prevents contact of the insects with the treated floor or wall surfaces and entry into rooms treated in this way. It is an essential advantage of the invention insect repellent compounds that despite their Volatility is very effective and permanent and for example 3 weeks or more of their repellent effect maintained. The compounds of the invention can together with insecticides for example with the against Cockroaches used boric acid powder are sprayed; in this way the cockroaches are sold immediately and then after volatilization  of the active ingredients upon their return from the insecticide destroyed.

The insect-repellent active compounds according to the invention can be used in many different ways However, they are best with detergents use, from which the neoalkanamides are surprising substantive on the treated or washed surfaces wind up. These cleaning agents work once in that they have an earlier insect infestation as well Stains and dirt that serves as food for the insects and it attracts, removes and repels the neoalkanamides leaves on the surface.

The essential component of the cleaning agents according to the invention is next to the insect repellent neoalkanamids a detergent substance such as soaps, preferably Sodium and / or potassium salts of higher C₁₀ to C₁₈ fatty acids or preferably anionic, non-ionic, amphoteric, ampholytic, zwitterionic or cationic Surfactants or mixtures thereof. Non-ionic and in particular anionic surfactants are preferred. These are in detail in "Surface Active Agents and Detergents", Volume II, pages 25-138, by Schwartz, Perry and Berch (1958) and by J. W. McCutchenon in "Detergents and Emulsifiers ".

Suitable anionic surfactants are soaps such as sodium, Potassium, ammonium or alkanolammonium salts, such as Triethanolamine salts; sulfates, Sulfonates, phosphates or phosphonates or salts of others suitable acids are used, but sulfates or sulfonates are preferred. This anionic Surfactants contain a lipophilic group with mostly 10 to 18 carbon atoms and preferably linear higher ones  Alkyl groups, albeit other lipophilic groups preferably having 12 to 16 carbon atoms such as branched chain Alkylbenzenes can be present. In some Cases of anionic surfactants may include lower polyalkoxy groups contained as with the ethoxylated higher Fatty alcohol sulfates e.g. B. triethoxylated lauryl alcohol sulfate. The number of ethoxy groups in these is low Surfactants generally in the range of 1 to 30 and preferably 1 to 10. Examples of suitable anionic Surfactants are fatty alcohol sulfonates such as sodium tridecyl sulfonate, Sodium salts of linear alkyl benzene sulfonates such as sodium tridecylbenzenesulfonate, olefin sulfonates and parraffinsulfonates. The anionic surfactants are mostly as a sodium salt, although for certain liquid compositions also potassium, ammonium and triethanolammonium salts are useful. The surfactant preferably contains a lipophilic alkyl radical 12 to 16 and preferably 12 to 13 carbon atoms.

Suitable non-ionic surfactants are usually condensation products of lipophilic compounds and lower alkylene oxides or polyalkoxy chains. Particularly preferred Lipophiles are higher fatty alcohols with 10 to 18 carbon atoms, however, alkylphenols such as octyl and nonylphenols can be used. The alkylene oxide is preferably ethylene oxide, usually 3 to 30 Moles of ethylene oxide present per mole of lipophilic group are.

The cleaning agents can contain suitable builders namely inorganic or organic, water-soluble or contain water-insoluble substances such as water-soluble ones inorganic salts including polyphosphates such as sodium tripolyphosphate, carbonates such as sodium carbonate, Bicarbonates such as sodium bicarbonate, borates such as borax  and silicates such as sodium silicate; also water-insoluble inorganic builders including Zeolites such as hydrated zeolite 4A, and water soluble organic builders such as citrates, gluconates, NTA and polyacetal carboxylates. If mild detergent are used, such as for treatment of the human body or sensitive textiles, the alkaline builders are reduced or left out entirely.

The cleaning agents can be a wide variety of additives contain, such as bentonite as a fabric softener, Perfumes and dyes Preventing redeposition of dirt like Sodium carboxymethyl cellulose, being in liquid compositions nor solvents or co-solvents can be used. Other additives are optical Brighteners, antistatic additives, bactericides, fungicides, Foamers, foam pressers, agents for improving the Flowability, suspending agents, antioxidants, antigelling agents, Means to increase dirt release and enzymes.

The cleaning agents according to the invention can be in particle form, as a powder, in tablets or pieces, as a liquid, Paste or gel, in capsules, as leaves, as Foam or aerosol or other suitable form be used.

Although the insect repellants according to the invention N-lower alkylneoalkanamides directly onto the objects it can be applied in many cases expedient and also more effective, the neoalkanamides in liquid solution or emulsion or as a liquid, particulate or use powdery dispersion. For this  the neoalkanamides in a suitable solvent like a lower alcohol e.g. B. ethanol or dissolved in an aqueous alcoholic medium; it can other solvents such as hydrocarbons, esters, Ketones, aldehydes and halogenated hydrocarbons are used such as isobutane or chlorinated or fluorinated lower hydrocarbons such as Dichlorofluoromethane, monofluorotrichloromethane and others Chlorofluoromethane, ethane and propane compounds. These compounds are liquefiable gases that are under Pressure in a dispensing container to be kept liquid can, for example, the areas to be treated to be able to spray better. The neoalkanamides can are also present in an aqueous or other emulsion, if a suitable emulsifier, a hydrotrope or a Surfactant is used. The neoalkanamides can too in particulate or powdered inert or active Materials such as silica, calcium carbonate, Clays, expanded polystyrene, wood chips and Sawdust. The neoalkanamides can also be active Components are dispersed, such as in detergent pellets in textile softening bentonites or in the boric acid used as a cockroach poison.

The insect-repellent preparations according to the invention can also be used in covering paper, wallpaper, wallpaper glue, carpets and floor coverings and documents incorporated for them will. You can use in floor wax, furniture polish and other surface treatment agents will. They can be used in certain areas such as warehouses or department stores using time-operated spray devices or other dispensers automatically be delivered; they can be sprayed from containers that are then used up with the products be loaded or refreshed again; you can  in absorbers and holding devices, for example can be applied to the underside of trash cans.

When using the insect repellent compound in A detergent contains the proportions of surfactant builder and neoalkanamide in a range of 1 or 5 to 35% by weight or 10 to 90% by weight and 0.2 to 10% by weight. Preferred detergents based on anionic or nonionic surfactants can still be water soluble Filler salts such as sodium sulfate and as an active component Contain N-methylneotridecanamide or neodecanamide. Particularly good cleaning agents contain 7 to 30 % By weight of surfactant, 20 to 75% by weight of builders, 0 to 50 % By weight of filler salts and 0.5 to 5% by weight of neoalkanamides.

When using liquid detergents with contains insect repellent neoalkanamides the same components may be present plus a liquid medium, but the surfactant is preferred is not soap. In some cases, common ones Emulsifiers, also hydrotropes such as sodium toluenesulfate and other common additives can be used. Liquid Detergents or detergents contain 2 to 25% surfactant, 5 to 50% by weight of builders, 2 to 10% by weight of neoalkanamide and 40 to 90% of liquid medium, mostly water. With a preferred liquid detergent composition are 3 to 20% anionic and / or non-ionic Surfactant, 10 to 20% builder salts such as water-soluble Products such as potassium pyrophosphate, sodium carbonate or Sodium polyacetal carboxylate and / or water-insoluble Builders such as sodium zeolite, and 0 to 20% water-soluble Filler salts such as sodium sulfate and 0.5 to 5% N-methylneodecanamide and / or N-ethylneodecanamide or other suitable neoalkanamides and the Rest of 50 to 90% consists of water, preferably desalinated water.  

Shampoos for upholstery and carpets can be 1 to 35, preferably 5 to 20% of a water soluble soap and / or surfactants, 0 to 40% builders and 0.2 up to 10% N-lower alkylneoalkanamides in an amount from 0.5 to 5% in a liquid, preferably aqueous Contain medium, which in an amount of 40 to 90 and preferably 70 to 90% is present. Alternatively the shampoo can also be in gel, paste or powder form are available.

When using the insect repellent preparations in hair shampoos for humans, these preferably consist of 2 to 25% soap and / or surfactants and 0.2 to 10% of mentioned neoalkanamides in an aqueous medium such as 40 to 90%, preferably demineralized water. The watery Medium can be up to half a co-solvent like a lower alcohol e.g. B. ethanol or a glycol contain; in general the proportion is such Co-solvent at 5 to 20%, based on the end product. Preferred shampoos contain 5 to 22% surfactant, 0 to 20% water-soluble filler salts, 0.5 to 5% N-lower alkyl neoalkanamides, preferably N-methyl or N-ethylneodecanamide and 50 to 90% preferably demineralized water.

Solid detergent in the form of pieces or flakes containing the insect repellant according to the invention Connections can also be used to wash people, Animals, household linen, carpets and / or for cleaning used by hard surfaces such as walls or floors will; these products in turn contain soap and / or Surfactants, builders, fillers and other additives, as mentioned above. The proportion of N-alkylneoalkanamides is in the range of 0.2 to 10%, while that Detergent makes up 15 to 95%. The soap bars  generally contain 2 to 20% water, the others Components are builders, fillers or others Additives; these range from 0.5 to 20% overall and in a range of 0.1 to 5% for the most individual components.

The cleaning agents mentioned can be used in any Way such as by spray drying, dry Mixing, by spray application and / or coating, by multiple dissolving and / or dispersing and / or Emulsifying, by grinding, extruding and pressing getting produced.

When the insect repellent compounds sprayed or applied in a carrier, the concentration should are sufficient to effectively drive away the insects.

The action time is greater when the active component themselves within an object, such as in a mattress or an absorbent sponge compared to spraying, dusting, Wiping or coating surfaces.

The concentration of insect repellent compounds in a liquid medium such as an aqueous medium together with a dispersing or emulsifying agent is usually in the range of 0.2 to 10 or 25 to 50%, but usually in a range from 0.5 to 10, such as 1 to 5% in the fight of cockroaches. In addition to water as a soluble medium can even lower alkanols such as ethanol, lower ketones such as acetone, lower hydrocarbons such as isobutane  and / or cyclopropane or chlorinated hydrocarbons be used.

When using the insect repellent compounds in powdery or particulate carriers, the Neoalkanamides liquid on powdered calcium carbonate, Silica, clay or boric acid or on granular ones Materials or on detergent particles or synthetic organic polymer beads with a preferred particle size from 125 µm to 2.4 mm diameter in concentrations from 0.2 to 10 or 25% and preferably 0.5 up to 5 or 10% applied to drive away cockroaches will.

The insect repellent compounds are generally on the surfaces to be treated with a concentration from 0.002 to 100 g / m² applied and remain on these areas, with application rates preferred in a range from 0.01 to 5 or 10 and in particular 0.1 to 2 g / m², for example 1 g / m² against Cockroaches can be applied. Concentrations outside this range is also possible, albeit sometimes with limited effectiveness. For detergents, which are used in an aqueous washing liquor such as water the concentration of active ingredient is generally in the range of 0.005 to 5% by weight, but can be used with hair shampoos or shampoos for carpets and upholstery higher and sometimes up to 25%.

With other surface treatment agents such as waxes or furniture polishes, the focus is essentially in the same range as for detergent compositions, can in some cases increase up to 25% will.  

The insect repellants according to the invention have significant advantages over other comparable ones Products. They are essentially non-toxic and therefore not dangerous for children or pets. They have a pleasant aromatic, sometimes fruity Odor, being N-methylneodecanamide and N-ethylneodecanamide apple-like or in terms of smell is peachy; consequently, they generally interfere not the aroma of the preparations in which they are used be, but even give these preparations a pleasant smell, so that expensive fragrances are no longer required. They are essentially colorless and can therefore be found in cleaning agents, Shampoos, polishes, sprayable products and other preparations in which the coloring plays a role plays, can be used with advantage. You are both as a contact agent as well as a gas repellent; they work against most insects, especially Cockroaches, the most difficult to keep away from the home are. The insect repellants according to the invention have a long lifespan of 2 weeks Cockroaches or more when applied topically. N-methylneodecanamide is opposite Anopheles quadrimaculatus 5 weeks active and at least a week longer as DEET. Against Aedes aegypti are the neoalkanamides more effective than DEET. They are in the different preparations such as cleaning agents, etc., stably regardless of the physical condition of these cleaning agents and stay above all from these funds highly substantive compared to the treated surface.

Experiments have shown that the N-alkylneoalkanamides according to the invention not only effective against cockroaches but also against other insects like flies, Fleas, lice, mosquitoes, bees, wasps, hornets,  Ants and other beetles as well as against arachnids like Spiders, ticks and mites.

Modify in the perfume preparations according to the invention the N-lower-alkylneoalkanamides smell of perfume, they are substantive to the areas on which the perfume is applied; they are also sufficient stable during storage and in contact with alkaline Substances and increase the effectiveness of flavors various other perfumed components. As a result The invention also relates to a novel liquid Perfume, which is used to perfume soaps and detergents is suitable, the perfume component being ethereal Oils, esters, ethers, aldehydes, alcohols, hydrocarbons, Ketones and lactones can exist, and the Content of the neoalkanamides in a range from 0.1 to 98% lies. The invention also relates to various Household products perfumed with this perfume are, such as soaps, detergents in any Form like particulate, liquid, gel-like, pasty or as a piece, also for abrasives, hair shampoos, Carpet and upholstery shampoos, floor care products, Furniture care products and masking paper. Furthermore, plastic objects contain the perfume according to the invention, such as pet care items, Feeding bowls, bed frames or care devices or items made of perfumed plastic or others Materials.

The normally liquid N-lower alkylneoalkanamides are sufficiently volatile and show a permanent Effect. They affect other perfume components and enhance or improve the aroma of such Components in the overall mix. The preferred N-ethylneodecanamide has a mild, somewhat rose-like aroma  with a slight plum-like or apple-like Fruitiness. The smell of a drop on a smell strip is still clearly noticeable after two weeks. N-methylneodecanamide has a light, fresh, fruity, pear-like aroma with a floral undertone; it is also on a smell strip after two weeks still noticeable. N-methylneoheptanamide has one green, fruity, wine-like smell that at least a day or two remains; Has N-methylneoheptamide a fresh, sour, camphor-like smell that also remains a day or two. The other N-lower- Alkylneoalkanamides are also aromatic and resistant and pull on the applied surfaces substantive on; they all have sufficient stability in numerous preparations and even in alkaline ones Preparations.

The N-alkylneoalkanamides can be used as a component in the Fragrance mixtures together with any known Perfume components, fixatives, solvents, extenders, Stabilizers and additives are used such as essential oils, esters, ethers, aldehydes, alcohols, Hydrocarbons, ketones and lactones, however also other products such as pyrrons and pyrroles.

Preferred components of the olfactory direction rose, lily, tropical fruit and flower / wood / amber are citrus, evergreen, jasmine, lily, rose, ylang-ylang in the essential oils; phenoxyethyl isobutyrate, benzyl acetate, p-tert-butylcyclohexyl acetate, guaiacaholzacetate, linalyl acetate, dimethylbenzylcarbinyl acetate, phenylethyl acetate, linalyl benzoate, benzyl format, ethyl methylphenyl glycidate, allylcyclohexane propylpropylate, stallyl; benzyl ethyl ether and aldehydes are alkyl aldehydes with 8 to 18 carbon atoms, bourgeonal, citral, citronellal, citronellyl, oxyacetaldehyde, cyclamenaldehyde, hydroxyzitronellal and lilial. Anethole, citronellol, eugenol, geraniol, linalol, phenylethyl alcohol and terpineol are used as alcohols. Possible hydrocarbons are balsams and terpenes and ketones are ionones, α- isomethylionone and methylcedryl ketone. Α- Alkyl lactones with 8 to 14 carbon atoms in the alkyl radical can be used as lactones. An example of the pyrrones is a hydroxy-lower alkylpyrrone with 1 to 4 carbon atoms in the alkyl radical; an example of the pyrroles is benzopyrrole.

The components mentioned above are preferably used in the perfumes according to the invention, but other perfume components are also used, such as lemon oil, lime oil, orange oil, bergamot oil, oils of sweet oranges, petitgrain, bigara oil, rosemary oil, dimethylanthranilate, indole, methylanthranilate, jasmine oil, patchouli oil, Vetiver bourbon oil, vanillin, ethyl vanillin, coumarin, 3-methylnonan- 3-yl acetate, methylionone, synthetic lily oil and rose oil, 3-methylnonan-3-oil, α- amyl cinnamic acid aldehyde, methyl salicylate, amyl salicylate, lavandin, isobyl ethyl acetate , neryl acetate, nerol, d-limonene, Cuminsäurealdehyd, linalyl propionate, Nerolidylacetat, Nerolidylformat, α-pinene, Isobutylinalool, methyl naphthyl ketone, Linalylisobutyrat, Paracresylcaprylat, Paracresylphenylacetat, sandalwood oil, coriander oil, sassafras oil, cassia oil, angelica root oil, Peruvian balsam, clover oil, Maceöl, menthol and almond oil .

In addition to the aroma components, fixatives can also be used like musk, civet, castoreum, ambergria, gum, benzoin, Musk ambrette, musk ketone, musk xylene, oleoresin orris root,  resinous benzoin siam and resinous Opopanax and numerous other resins, gums, synthetic Types of musk and other fixatives can be used. Furthermore, other perfume components such as alcohol and other suitable solvents and media as well Preservatives, antioxidants, stabilizers and viscosity and volatility modifiers be used.

The perfumes according to the invention can contain 0.1 to 98% N-lower Alkylneoalkanamides contain while the rest others Flavorings and perfume ingredients, like solvents, liquid media and / or particulate or powdery raw materials such as wood particles, base materials and clays. The perfume is preferably in liquid Condition, especially in a lower alcoholic Solvents like ethanol before and the concentration of N-lower alkylneoalkanamides is in one range from 1 to 60%, preferably from 2 to 30 and in particular in the range of 5 to 15 such as 10%. The The proportion of fixatives is less than that of the aroma components and is usually in the range of 0.1 to 5%. The proportion of the solvent can range from Fluctuate from 20 to 95% and preferably from 50 to 90% and can be used with some perfumes that are used as concentrates be completely omitted if, for example the perfume to a product or to a composition and not a common handkerchief perfume is given.

Although the proportions of the different aroma components fluctuate and the individual components make up 0.01 to 30% can and sometimes certain representatives of this Components are omitted from the wording  can, at least in the perfume formulations an ester, at least one aldehyde and at least one Alcohol present. The proportion of each of these products from the respective class is at least 1%, and wherein at least one component of such Class in an amount of at least 5% and usually at least 10% is present. In other cases, however one or more of the three typical representatives of this Flavor classes may be omitted, such as in the preferred floral / woody / amber perfumes that 5 to 40% Zitrenellol, 5 to 30% Geraniol and 2 to Contain or preferably 40% phenylethyl alcohol 5 to 20 or 5 to 25 and 2 to 15% or for example 8 or 10 or 5%. The total content of aroma components except for the N-methylneoalkanamide is usually in a range from 5 to 99% and preferably from 50 up to 90%, with the high proportions in the mostly solution-free Concentrates occur.

The percentage of perfume in the various household products and other products according to the invention with the concentrates usually used without solvents in a range of 0.1 to 10 and preferably from 0.5 to 5 and mostly at 1 to 3%, the content of lower alkylneoalkanamides usually in one Range from 0.01 to 5, preferably 0.1 to 2 and usually 0.2 to 1%. Perfuming odor improvers or air freshening sprays, the perfume content increased to 5 to 25 and even up to 50% in some cases, the perfume concentrate can also be used undiluted.

The perfumes according to the invention can be used in a wide variety of ways Household products and in numerous other compositions and objects are used, such as  for cleaning agents of all kinds Type, means of repelling insects, insecticides, Paper products, textiles, surface treatment agents and plastic objects. The insect repellant Agents can be liquid, gel-like, pasty, are powdery or in any other suitable form; the same applies to insecticides used with the invention Agents are perfumed, although insecticides generally in a liquid solvent or dissolved in a liquefied gas or in an emulsion occur. Wear the N-lower alkyl neoalcanamides So with the different household products and objects both for perfuming and for repelling of insects.

example 1

N-methylneodecanamide was prepared from methylamine and neodecanoyl chloride in a 1 liter three-necked flask with stirrer, thermometer and dropping funnel and condenser with a drying tube attached. The flask in an ice bath was charged with 31 g of methylamine, 7 ml of diethyl ether and 59 g of triethylamine, the latter serving to remove HCl formed during the reaction. 190.5 g of neodecanoyl chloride were then added dropwise over the course of an hour, after which the reaction mixture was allowed to warm to room temperature. The reaction mixture was then washed twice with deionized water in a 2 liter separatory funnel to separate the N-methylneodecanamide from the triethylamine chloride; it was then washed once with 5% hydrochloric acid and then with 5% aqueous sodium hydroxide solution and finally with distilled water until the washings were neutral to Lakmus. The ether was then removed from the mixture on a steam bath and then in a vacuum rotary evaporator. N-Methylneodecanamide was obtained in practically stoichiometric yield; after distillation at 235 ° C. under 760 mm Hg, it was a pure water-white product with the infrared spectrum shown in FIG. 1.

In the same way, N-ethylneodecanamide, N-methylneotridecanamide, N-ethylneotridecanamide, N-methylneoheptanamide and N-ethylneoheptanamide were prepared, molar amounts of the corresponding alkylamines such as ethylamine, methylamine, ethylamine, methylamine or ethylamine, triethylamine and neoalkanoylchloride, Neotridecanoyl chloride, neotridecanoyl chloride, neoheptanoyl chloride or neoheptanoyl chloride are used. The same volume of 700 ml diethyl ether was also used, using the same equipment and reaction and purification conditions. The products were obtained essentially in stoichiometric yields. Some of their infrared spectra are shown in Figs. 2-4.

Example 2

The six compounds were prepared according to Example 1, but using the corresponding neoalkanoic acids instead of the acid chlorides; no triethylamine was used. In these reactions, in which the stoichiometric proportions of the neoalkanoic acid and the alkylamines and diethyl ether were used as the reaction solvent, a 1 l three-necked flask was also used, but in a closed system to avoid alkylamine losses. The flask had a heating mantle, a magnetic stirrer, a nitrogen feed that reached below the surface of the reaction mixture, and a thermometer and thermostat to regulate the reaction temperature, which was kept at 240 ° C. for 5 hours. The reaction products were isolated, washed and freed of ether analogously to Example 1. The infrared spectra of the products are shown in FIGS. 1 to 4.

Example 3

The N-methylneodecanamide prepared according to Example 1 was opposed to its insect repellent effect Cockroaches examined, taking 1 g substance in 10 ml acetone dissolved and in a bowl with an inner surface of 188.5 cm² was pivoted so that after evaporation of the acetone 0.0189 g of the N-methylneodecanamide evenly on the inside surface of the bowl in a concentration with 1.0 g m² was distributed. There were four openings cut at the same distance on the edges of the bowl, so that it is possible for the insects to be examined was under the upside down and on a flat surface crawling lying shell. It became an identical one Control bowl made, but only the equal amount of acetone was applied alone. Each Shell was centered in the middle of one half divisible rectangular area into a box 100 cockroaches were. The box was with a clear pane sealed to prevent the cockroaches from crawling out. The box was originally in the dark, however a 100 watt Light bulb, about 50 cm above the box, attached. All the cockroaches trying to avoid the light crawled under one of the overturned bowls. The difference in numbers showing cockroaches crawling under the two shells the repellent effect. After a minute of lighting a cutting disc was placed in the box,  to separate the test area from the control area whereupon the shells removed and the cockroaches in each Department were counted. The number of cockroaches in the control area corresponds to the percentage effectiveness of the insect repellent. After two days it was found that N-methylneodecanamide was 100% effective compared to the control attempt. After two days became N-methylneodecanamide (NMNDA) with DEET and opposite another good cockroach repellent MGK-874 tested, with NMNDA 9 times and 19 times more effective than the other insect repellent preparations. Five days after application of the preparations showed a similar test that NMNDA was even more effective and this comparatively better effectiveness even after Showed 14 days. After 21 days, neither had the trial product nor the comparison products a repellent Effect.

Fig. 5 shows a graphical representation of the comparative effectiveness in percent of N-methylneodecanamide compared to DEET in the rejection of cockroaches. The number of cockroaches collected under the DEET-treated bowl is recorded for each of the specified days after application of the preparations. The comparable effectiveness of the compound NMNDA to be investigated in percent corresponds to the number of cockroaches hiding under the shell prepared with DEET, for 100 insects used. If the experiment was modified, only the inner parts of the floor, i.e. the upper area of the inverted shell, were coated with the various experimental and comparison products at the same concentration of 1 g / m². The results gave the same effect as in the contact experiments described above, but the absolute effectiveness of the products was expected to be lower due to the lower amounts of the applied preparation and the fact that the preparations were not on the lower and inner surface of the dishes, which were from the cockroaches are preferably occupied, so that the repellent effect was only due to the evaporation and mostly because of the contact.

The test results are the same and independent of whether the insect repellent compounds through direct condensation of neoalkanoic acids or from neoalkanoyl chlorides were obtained. Similar results can be with other Neoalkanamiden according to the invention obtained as with N-ethylneodecanamide, N-butylneodecanamide, N-methylneotridecanamide, N-ethylneotridecanamide, N-methyl and N-ethyl-neoheptanamide, -neononanamide, -neoundecanamide and -neododecanamide. The best insect repellent Effect was obtained with the neoalkanamides, the liquid and sufficient under normal conditions are volatile so that the fumes from the insects are perceived and act as a deterrent.

The insect repellants can also come from spray containers or as an aerosol with a mixture of isobutane / Cyclobutane (50:50) or dichlorodifluoromethane and trichloromonofluoromethane (60:40) or with others pressurized solvents are sprayed, with concentrations ranging from 2 to 30% depending on Extent of solubility of the compounds in the solvent can be used, such as 15% Chlorofluoromethane or 20% in a hydrocarbon system, 5% in ethanol and 25% in methyl ethyl ketone. In aqueous systems with preferably emulsifiers or suitable surfactants to achieve a homogeneous The concentrations are usually somewhat in suspension lower than organic solvents, namely  for example at 3, 5 and 7%. All liquid systems can be applied with cloths, swabs, spray cans and nozzles will; gels or pastes can also be used will.

During practical tests on kitchen floors, counters, Drain boards, walls, in kitchen cupboards and dishwashers, under ice cabinets and in cockroach infestations Apartments were significantly less cockroaches in the areas found with the insect repellant according to the invention Agents were treated compared to corresponding ones Control areas. There were fewer Scraping on the floors and boards of cabinets and Pantry found if the walls of the inventive Funds had been treated, namely especially with N-methylneodecanamide and N-methylneotridecanamide, which is not about contact but also act on the gas phase. Treatment of floors, Walls, counters, pouring basins, cupboards, windows and Doors or carpets in a house or apartment clearly shows that treatment with N-methylneodecanamide, N-ethylneodecanamide or N-methyltridecanamide Cockroach infestation is significantly reduced. Because of the original presence of the vermin however, one or two weeks and in some cases the insect repellent must be applied several times will. In some cases, the application rates increased up to 10 g / m² while in other cases could be reduced to 0.01 g / m² or lower.  

Example 4

Analogously to Example 1, N-methylneotridecanamide (NMNTDA) was prepared from neotridecanoyl chloride and methylamine with the stoichiometric use of the two reactants. The starting material for the neotridecanoyl chloride was a neotridecanoic acid in the form of a mixture of neo acids with 12 to 14 carbon atoms, an acid number of 273 and a specific density at 20 ° C. of 0.9117 g / cm³. The reaction product was purified analogously to Example 1 and gave the spectrum shown in FIG. 4.

The N-methylneotridecanamide so produced had one weak pleasant tobacco-like smell and showed proved to be exactly the same in a test analogous to Example 3 good or even better than N-methylneodecanamide Cockroaches; it had 100% effectiveness 14 days after 25 days an effectiveness of about 60%, while for N-methylneodecanamide values of 11 Days and 17 days were measured.

The essentially the same synthesized N-methylneodecanamide was less effective than N-methylneotridecanamide.

Example 5

N-methylneodecanamide (NMNDA) was at a suitable concentration from Z. B. 10% dissolved in acetone and with a Concentration of 1 g applied to 280 cm² of a stocking, which after two hours than all of the acetone had evaporated through a nylon stocking on her arm was touched on a test person, whereupon the so covered Arm placed in a cage with adult mosquitoes which are rejected by DEET, namely the Species Aedes aegypti and Anopheles quadrimaculatus.  

If less than 5 mosquitoes pass through the subject the stocking with a one-minute dwell time of the arm Bite in the mosquito cage, the test was completed 24 hours later repeated and then again with less than five Mosquito bites repeated weekly until inside five stitches were obtained in one minute. The extent The rejection by the products was considered the number of Days determined from the time of application until reaching of five mosquito bites when the Arm of the test subject was reached within one minute will.

At Aedes aegypti, DEET was 22 days and reached a value of 15 days with NMNDA during with Anopheles quadrimaculatus the values 29 and 36 Days. As a result, the N-lower alkylneoalkanamide acts regarding the rejection of mosquitoes like DEET.

In practical use on the human body Apply an appropriate solution in a skin lotion or a cream or in an aerosol spray NMNDA acts like DEET and gives at least one Hour protection against Aedes aegypti and Anopheles quadrimaculatus when applying 0.3 g to the forearm of a human. Similar results will be obtained with others Alkyl neoalkanamides such as N-ethylneodecanamide, N-methylneotridecanamide, N-ethylneotridecanamide, N-methylneononamide and N-ethylneoundecanamide and mixtures thereof receive.  

Example 6

It became a detergent of the following composition produced:

Ingredients% by weight

Linear sodium tridecylbenzenesulfonate 20.0 sodium tripolyphosphate 40.0 sodium carbonate 10.0 sodium bicarbonate 10.0 borax 5.0 proteolytic and amylolytic
Enzyme on carrier powder 1.0 sodium carboxymethyl cellulose 0.5 optical brightener 1.0 N-methylneodecanamide 2.0 water 10.5 100.0

All ingredients except enzyme powder and the insect repellent were in a crutcher Slurry mixed and into hollow beads with a particle size corresponding to a 10 to 100 US Standard sieve spray dried. Then that was  Enzyme powder mixed in and the insect repellent Liquid sprayed into a circulating drum. Instead of NMNDA can also be used by N-methylneotridecanamide will. The textiles washed with this detergent show a better insect repellent effect than that laundry washed with comparative products.

Example 7

An abrasive was made from the following ingredients produced:

Ingredients% by weight

Finely divided SiO₂ powder 97.5 linear sodium dodecylbenzenesulfonate 2.0 N-ethylneodecanamide 0.5 100.0

Example 8

It became a liquid all-purpose cleaner of the following Composition made:

Ingredients% by weight

Non-ionic surfactant *) 1.0 linear sodium dodecylbenzenesulfonate 2.0 sodium cumene sulfonate 5.0 sodium carbonate 5.0 sodium bicarbonate 1.0 optical brightener 0.02 dye 0.01 N-methylneononanamide or
N-methylneodecanamide 1.0 demineralized water 84.97 100.0

*) The non-ionic surfactant was a condensation product from 1 mole of a higher fatty alcohol mixture 10 carbon atoms and 5 moles on average Ethylene oxide.  

Example 9

It became a liquid all-purpose cleaner of the following Composition made:

Ingredients% by weight

Linear sodium dodecylbenzenesulfonate 3.7 Sodium sulfate 3.3 Soda ash 4.0 Sodium bicarbonate 2.0 Non-ionic surfactant *) 2.0 Isopropyl alcohol 1.8 Distilled coconut oil fatty acids 0.5 Dye as a 0.1% aqueous solution 0.6 Perfume 0.8 Softened water 80.3 N-methylneotridecanamide 1.0

*) The non-ionic surfactant was a condensation product from 1 mole of a mixture of higher fatty alcohols with 9 up to 11 carbon atoms with 6 moles of ethylene oxide.

The pH value of the insect-repellent liquid all-purpose cleaner was made up with either sulfuric acid or soda 10.5 ± 0.2 set. The cleaner obtained had one excellent insect repellent effect and thus cleaned surfaces and objects or the surfaces those of this product in concentrated or diluted form had contained one on the surface small proportion of N-methylneotridecanamide and were thus insect repellent.  

Example 10

It became a liquid detergent based on Pine oil produced as follows:

Ingredients% by weight

Sodium paraffin sulfonate 6.8 isopropanol 7.0 surfactant *) 4.0 pine oil 10.0 N-methylneotridecanamide 10.0 sodium sulfate 3.8 demineralized water 58.4 100.0

*) The surfactant was a condensation product from one mole of a higher fatty alcohol mixture with average 12 to 13 carbon atoms and 6.5 moles Ethylene oxide (Neodol 23-6.5).

By using this agent as a cleaner in concentrated or diluted form remains on the Surface of the insect repellent up to 3 weeks effective.

Example 11

The following were used to make a carpet cleaner Components selected:  

Ingredients% by weight

Sodium salt of lauric acid mono-
ethanol sulfosuccinate 30.0 enzyme mixture with lipolytic,
proteolytic and amylolytic
Enzymes 2.0 sodium tripolyphosphate 20.0 sodium hexametaphosphate 5.0 sodium monophosphate 3.5 sodium bicarbonate 20.0 urea 8.0 calcium silicate 10.0 N-methylneoundecanamide       100.0

The calcium silicate was a hydrated synthetic Product (Micro-Cel).

This concentrate was proportionate before use Diluted 1: 3 with water, 100 g being sufficient to about Treat 10 square meters of carpet.

Example 12

It became an upholstery cleaner of the following Composition made:  

Ingredients% by weight

Anionic surfactant 10.0 Aqueous ammonia (28%) 30.0 Water 58.5 N-methylneodecanamide 1.5 100.0

Linear alkylarylsulfonic acid (sulframine OBS) is used.

Before using this upholstery cleaner, it was in a volume ratio of 1: 3 with a solvent diluted according to Stoddard.

Example 13

The following were used to make a hair shampoo Ingredients used:

Ingredients% by weight

Ammonium monoglycerol sulfate 22.0 hydroxypropylmethyl cellulose 1.0 polyacrylamide 1.0 N-methylneodecanamide 1.0 demineralized water 75.0 100.0

Example 14

It became a skin cream of the following composition produced:

Ingredients Quantity

Yellow ceresin wax 56.5 g Yellow beeswax 56.5 g Stearic acid 56.5 g Petrolatum, white 113.0 g White mineral oil 240.0 ml Water 180.0 ml Borax 8.4 g Triethanolamine 15.0 ml

All components except for the borax dissolved in the hot water and the triethanolamine were melted at 71 ° C. using the hot borax solution is stirred and after cooling at Thicken with 10 g of N-methylneodecanamide.  

Example 15

A body lotion made from the following ingredients produced:

Components parts by weight in g

Glycerol monostearate 50.0 Oleic acid 30.0 Mineral oil 15.0 Lanolin 10.0 Triethanolamine 12.0 Sodium lauryl sulfate 10.0 Preservative 10.0 Desalinated water 980.0 N-ethyl neonanamide 12.0

Example 16

There was a bar soap from the following components produced:

Ingredients% by weight

Soap 88.0 N-methylneoundecanamide 1.0 titanium dioxide 1.0 tin chloride as preservative 0.2 water 9.8 100.0

A tallow / coconut sodium soap (80:20) was used as the soap. used.  

Instead of soap bars, you can also use soap bars synthetic surfactant can be prepared by instead of up to 25% of the soap, coconut monoglyceride sulfate used. Analog can also be used accordingly softened, fully synthetic surfactants for manufacturing of soap bars can be used.

Preservative, titanium dioxide, the insect repellent Component and water were dried with the Soap flakes, containing about 8% water, worked through and stranded and then cut into soap bars and pressed. Laundry soap for textiles can be added from 20 to 40% by weight of builders such as sodium tripolyphosphate and / or sodium carbonate are produced, wherein one usually improves the moisture content Plasticity increased during processing. Composed Detergent pieces and synthetic textile detergent pieces can also be produced, the content of insect repellent can be increased by up to 5% can.

Example 17

It became an anti-repellent spray from the following Ingredients manufactured:

Ingredients% by weight

Dichlorodifluoromethane 55.5 trichloromonofluoromethane 45.5 mineral oil 4.0 N-methylneodecanamide 5.0 100.0

The mineral oil and the N-methylneodecanamide were in the pressurized blowing agent mixture dissolved in filled an aerosol container.

Example 18

For the production of a powdery insect repellent 99% powdered clay with 1% N-methylneodecanamide were used mixed.

Example 19

The following were used to make a floor wax Components used:

Ingredients parts by weight

Montanester wax 6.0 polyethylene wax 4.0 non-oxidized micro-
crystalline wax 5.0 tall oil fatty acid 0.2 aqueous potassium hydroxide solution
(43%) 0.5 N, N-diethylaminoethanol 1.0 methyl carbitol 1.0 N-propylneoheptanamide 2.0 water 80.3
100.0

Example 20

To produce a furniture polish, the uses the following components:  

Ingredients parts by weight

Carnauba Wax 5.0 Beeswax 5.0 Ceresin Wax 5.0 Silicone Oil (DC 200) 5.0 Stoddard Solvent 40.0 Sodium Soap
(75: 25 tallow / coconut soap) 2.0 water 130.0

A wax / silicone concentrate was made by heating the Stoddard solvent gradually to about 52 ° C Add the previously melted waxes and the Silicone oil produced with stirring. At the same time, the Soap dissolved in water at a temperature of 90 ° C and then hot with the wax dispersion with vigorous Stir mixed. The mixture was then quickly opened Cooled to room temperature and with 385 parts of water, 71 Parts of naphtha and 15 parts of N-methylneodecanamide slowly transferred. 71 parts of dichlorodifluoromethane were used as Blowing agent used to mix this in one Dispensing container to bring.

Example 21

This was used on both sides for the production of lay-out paper with liquid N-methylneodecanamide in a volatile Sprayed solvent such as acetone, followed by the webs Evaporation of the solvent was rolled up again. The share of insect repellent is reduced to 2% set, although in some cases only 0.1% can be used. This topping paper has a long life Storage time before use because of a loss Active substance by evaporation by rolling up the Paper web is prevented.  

In another case the insect repellent became Neoalkanamide during the manufacture of the paper pulp added, but care should be taken must that in the training and paper production insect repellant does not evaporate on drying.

Example 22

It became an insect repellent for trash cans prepared by using N-methylneodecanamide in 2% Solution used to impregnate a sponge; The neodecanamide was used in the interior of a flat cylindrical polyurethane foam molded in an open holder on the inside of the lid a common kitchen waste container with a foldable Lid was attached.

Example 23

For the production of an insect repellent insecticide 98% by weight of boric acid were mixed with N-methylneodecanamide.

The numerous products according to Examples 5 to 23 are excellent in its effect as an insect repellent Medium and especially against cockroaches. The Possible uses and uses of the However, compositions according to the invention are varied.

Example 24

It was from the N-alkylneoalkanamides according to the invention made a perfume of the following composition:  

Ingredients% by weight

p-tert-Butylcyclohexyl acetate 12.0 N-ethylneodecanamide 10.0 linalool 10.0 geraniol 10.0 benzyl salicylate 10.0 benzyl acetate 10.0 citronellol 8.0 terpineol 8.0 α- isomethyl ions 6.0 linalyl acetate 5.0 phenylethyl alcohol 5.0 methyl cedryl ketone 3.0 ionone ( α / β ) 1.0 hydroxycitronellal methyl
anthranilat - Schiff'sche Base 1,0 Ambreinverbindung (CEFE No. 2)
[Colgate] 1.0 100.0

The individual components were mixed together obtained a perfume with a forest / flower / amber aroma has been. The one contained in the fragrance composition Neodecanamide had a harmonizing effect and strengthened the smell; apparently it also strengthens the perfume and makes it more permanent. It became similar achieved good effects if instead of N-ethylneodecanamide now N-ethyl neodecanamide or other N-lower Alkylneodecanamides or mixtures thereof are used were. In particular, this results in N-methylneodecanamide a harmonization and a floral smell in harmony with the other perfume ingredients, whereby the aroma is enhanced.  

Example 25

It became a perfume using the following Components made:

Ingredients% by weight

Styrallyl propionate 20.0 N-ethyl neodecanamide 15.0 α- decalactone 10.0 anethole 10.0 benzyl acetate 10.0 ethyl methylphenyl glycidate 5.0 benzyl format 5.0 dimetol (Givaudan) 5.0 hydroxyethylpyrrone in 1%
Solution in diethyl phthalate 5.0 allylcyclohexane propionate 5.0 α -nonalactone 5.0 linalyl benzoate 4.0 ylang ylang extract 1.0 100.0

The components were mixed together and gave a tropical fruity aroma, which for household product such as detergents, soaps and suitable for cosmetics was. The N-ethyl neodecanamide enhances the aroma and improves substantivity and permanence; it also contributes to a natural fruity and less lactonic smell. Instead of the N-ethylneodecanamide can also other N-lower-alkylneoalkanamides such as N-methyldecanamide, N-ethylneoundecanamide, N-ethylneononanamide, N-n-propylheoptanamide and N-isopropylneotetradecanamide be used. Each of the  Neoalkanamide mentioned has a different smell note and all have different stabilities, substantivities, Dwell times and fragrance notes; however they are all suitable for perfumes and contribute to the properties the total fragrance grade of the perfume compounds or the ready-to-use products, the so-called handkerchief perfumes at by dissolving in 5 parts of ethanol can be obtained.

Example 26

It was a perfume made from the following ingredients produced:

Ingredients% by weight

Zitronellol 25.0 phenylethyl alcohol 25.0 N-ethylneodecanamide 10.0 geraniol 10.0 phenoxyethyl isobutyrate 3.9 linalool 3.0 p-tert-butylcyclohexyl acetate 3.0 geranyl acetate 2.0 eugenol 2.0 phenylethyl acetate 2.0 benzyl acetate 2.0 α / β- ionon 2.0 lauryl aldehyde (10% solution in
Diethyl phthalate 2.0 α / isomethyl ionone 2.0 dimethylbenzylcarbinylacetate 1.0 guaiacholzacetate 1.0 Rose-Oxide R (10% solution in
Diethyl phthalate) 1.0 ylan ylang 1.0 undecylene aldehyde (10% solution in
Diethyl phthalate) 1.0 damascenone, 1% solution in
Diethyl phthalate [Firmenich] 1.0 Citral 1.0 100.0

The above ingredients were mixed together to get a perfume with a rose-like character, where the N-ethylneodecanamide the fruit ester effect the rose scent in a sugary jam-like Brings quality while the ionones are suppressed. In addition, the perfume is strengthened and his Substantivity and constancy increased.  

Example 27

It was a perfume made from the following ingredients produced:

Ingredients% by weight

Hydroxyzitronellal (synthetic) 28.0 N-methylneodecanamide 20.0 cyclamaldehyde 1.0 geraniol 20.0 citronellol 15.0 Brahmanol 10 (dragoco) 5.0 phenylethyl alcohol 3.0 heliotropin 2.0 indole (10% solution in diethyl phthalate) 2.0 α / β- ionon 1.0 α -nonalactone 1.0 Lilial (Givaudan) 1.0 citronellyloxyacealdehyde 0.5 Bourgeonal (Naarden) 0.5 100.0

The perfume was created by mixing the individual ingredients received and had a lily-like fragrance. Due to the presence of N-methylneodecanamide the overall fragrance is made sweeter and more natural, especially when drying; the composition was reinforced and the substantivity on the substrates increased, the resistance after application or Commitment. When installing this perfume in household products such as detergents, cleaning agents, polishing agents and Shampoos it shows a pleasant fragrance, is substantive, resistant and stable and also has insect repellent  Properties as they are especially for Carpet shampoos, surface cleaning agents for walls and floors, for cosmetic lotions and fragrances are desired.

If other lower alkyl neoalkanamides instead of N-methylneodecanamides are used, such as N-ethylneodecanamide, N-butylneooctanamide and N-methylneotridecanamide, similar effects will be obtained.

Example 28

A detergent consisting of the following ingredients became produced:

Ingredients% by weight

Linear sodium tridecylbenzenesulfonate 20.0 sodium tripolyphosphate 37.0 sodium carbonate 10.0 sodium bicarbonate 10.0 borax 5.0 enzyme mixture (proteolytic and
amylolytically on a powder carrier) 1.0 sodium carboxymethyl cellulose 0.5 optical brightener 1.0 perfume (according to Example 24) 5.0 water 10.5 100.0

All components of this detergent with the exception of Enzyme powder and perfume were mixed in mixed in an aqueous slurry and hollow Spray-dried detergent pellets, their particle size  in a range of 10 to 100 U.S. mesh sieves lay. The enzyme powder was then spray-dried with the Beads mixed and perfumed in liquid State sprayed onto the mixture while this was circulated in a mixer. Through the N-alkylneoalkanamide was washed with this detergent Laundry more insect repellent than the usual Laundry detergents.

The N-lower-alkylneoalkanamides according to the invention can be used in a variety of other perfume formulations be used and show because of their sufficient Liquid, good substantivity and their adherence on the treated surfaces even when applied excellent effects from dilute liquid media, without significantly changing the smell; furthermore, the components according to the invention are stable and even alkali-resistant and are up to two weeks or more effective. Modify and reinforce them the other perfume components and thus result in one final smell with enhanced aroma and enhanced Effect.

You can be independent of the numerous products according to Examples 6 to 23 and 28 still varied Be used as an insect repellent and are particularly suitable for such products that are difficult to perfume. For example are those at perfume concentrations corresponding to 0.3% with N-methylneodecanamide or 0.3% with N-ethylneodecanamide in chlorinated powdery abrasives themselves after two weeks of storage at an elevated temperature of 49 ° C excellent, pleasant smells of good Color stability. The same excellent stabilities in terms of smell and color are also evident  Neoalkanamidamide concentrations of 0.2% in one Detergent based on synthetic surfactants Phosphate builders and at 1% in a toilet soap. The proportions of the perfume are usually at 2 to 20 times or 5 to 10 times the proportion N-lower alkyl neoalkanamides in this product. There these products generally do not work at temperatures up to 49 ° C, the storage tests show that even volatile constituents are still effective maintained, which means that the products with the Alkanamides are stable much longer at room temperature are.

Claims (33)

1. N-lower alkylneoalkanamides, whose alkyl radicals 1 to 4 Carbon atoms and their neoalkanoyl group 7 to 14 Has carbon atoms. 2. N-lower alkylneoalkanamides according to claim 1, characterized characterized in that the lower alkyl radical 1 to 2 Carbon atoms and the neoalkanoyl group 9 to 11 Contains carbon atoms. 3. N-lower alkylneoalkanamides according to claim 2, characterized characterized in that the neoalkanoyl group neodecanoyl is. 4. N-lower alkylneoalkanamides according to claim 1, characterized characterized in that the lower alkyl radical 1 to 2 Carbon atoms and the neoalkanoyl group about 13 Has carbon atoms.   5. N-methylneodecanamide. 6. N-ethylneodecanamide. 7. N-methylneotridecanamide. 8. N-ethylneotridecanamide. 9. Detergent for hard or soft surfaces to this to make insect repellent, characterized by that it's a soap or a synthetic organic detergent substance in a detergent Proportion and N-alkylneoalkanamide in an insect repellent Contains amount whose alkyl radical 1 to 4 Carbon atoms and its neoalkanoyl group 7 to 14 Has carbon atoms. 10. Particulate textile detergent according to claim 9, characterized in that it contains 1 to 35% by weight of a anionic, non-ionic, amphoteric, ampholytic or zwitterionic surfactants, 10 to 90% by weight Builders and 0.2 to 10% by weight of one or more Contains N-lower alkylneoalkanamides. 11. Detergent according to claim 10, characterized in that there is 7 to 30 wt .-% of anionic and / or non-ionic surfactants, 20 to 75 wt .-% water-soluble and / or water-insoluble builders, 0 to 50 % By weight of water-soluble filler salts and 0.5 to 5% by weight N-lower alkylneoalkanamides having 1 to 2 carbon atoms contains in the lower alkyl radical. 12. Liquid detergent according to claim 9, characterized characterized in that it contains N-lower-neoalkanamides, whose neoalkanoyl group has 9 to 11 carbon atoms  having. 13. Detergent according to claim 12, characterized in that it is 3 to 20 wt .-% anionic and / or nonionic Surfactants, 10 to 30 wt .-% water-soluble and / or water-insoluble builders, 0 to 20% by weight water-soluble filler salts, 0.5 to 5% by weight Contains N-methyldecanamide and 50 to 90 wt .-% water. 14. Shampoo according to claim 9 with insect repellent Properties, characterized in that 2 to 25 % By weight of an anionic, nonionic, amphoteric, ampholytic and / or zwitterionic surfactants and 0.2 to 10 wt .-% of one or more N-lower alkylneoalkanamides contains in an aqueous medium. 15. Carpet shampoo, characterized in that it is 1 to 32 % By weight of a water-soluble soap, anionic, non-ionic amphoteric, ampholytic and / or zwitterionic surfactants, 0.2 to 10 wt .-% or several N-lower-alkylneoalkanamides and 0 to 40% by weight Contains builders in a liquid medium. 16. Solid insect repellent detergent in Bar shape, characterized in that it is soap and / or surfactants and N-alkylneoalkanamides in one contains insect repellent amount, the alkyl group 1 up to 18 carbon atoms and their neoalkanoyl group 7 has up to 14 carbon atoms. 17. Detergent piece according to claim 16, characterized in that that it is anionic, non-ionic, amphoteric, ampholytic and / or zwitterionic surfactants and Contains N-alkylneoalkanamides, the alkyl group of 1 to 4 Carbon atoms and their neoalkanoyl group 9 to 11  Has carbon atoms. 18. soap bar according to claim 16, characterized in that it's a soap made from a mixture of higher fatty acids with 10 to 18 carbon atoms and N-alkylneoalkanamides contains whose alkyl group contains 1 to 4 carbon atoms and their neoalkanoyl group 9 to 11 carbon atoms having. 19. Insect repellent composition, characterized in that they alkylneoalkanamides, the alkyl radical 1 up to 18 carbon atoms and their neoalkanoyl group 7 has up to 14 carbon atoms in a liquid Contains medium dispersed or dissolved. 20. Composition according to claim 19, characterized in that the alkyl radical of the N-alkylneoalkanamides 1 to 2 Carbon atoms and the neoalkanoyl group of these 9 to Contains 11 carbon atoms and that the N-alkylneoalkanamide with a concentration of 0.2 to 25% by weight is dispersed in an aqueous medium. 21. A composition according to claim 20, characterized in that the N-alkylneoalkanamide in a liquid solvent with a concentration of 0.2 to 25% by weight is solved. 22. A composition according to claim 21, characterized in that it N-methyl or N-ethyl neodecanamide in an amount of 0.5 to 10% by weight in a liquid solvent contains which is a gaseous under normal conditions Hydrocarbon or halogenated hydrocarbon is under sufficient pressure Room temperature is liquid.   23. Procedure to insect areas or objects to make, characterized in that one these areas or objects or nearby applies the same N-alkylneoalkanamides whose Alkyl radical 1 to 18 carbon atoms and their Neoalakanoylgruppe has 7 to 14 carbon atoms. 24. The method according to claim 23, characterized in that the alkyl radical of the neoalkanamide 1 to 2 carbon atoms and the neoalkanoyl group neodecanoyl is. 25. The method according to claim 23, characterized in that the neoalkanamide is applied with a cleaning agent which contains a soap or a surfactant, and that the N-lower alkylneoalkanamides have 1 to 4 carbon atoms have in the lower alkyl radical and Neoalkanoyl group has 9 to 11 carbon atoms. 26. The method according to claim 23, characterized in that the N-alkylneoalkanamides in an amount of 0.2 to 10 g / m² be applied. 27. Perfume, characterized in that there are one or more Contains N-lower alkylneoalkanamides, the lower Alkyl radical 1 to 4 carbon atoms and their neoalkanoyl group Has 5 to 14 carbon atoms, and at least one perfume component from the group of essential oils, esters, ethers, aldehydes, alcohols, Contains hydrocarbons, ketones and lactones, where the content of neoalkanamides in a range of 0.1 up to 98% by weight.   28. Perfume according to claim 27, characterized in that it is in liquid form and the neoalkanoyl group the N-lower alkylneoalkanamides have 7 to 14 carbon atoms has and the content of neoalkanamides in the Perfume ranges from 1 to 60% by weight. 29. Perfume according to claim 28, characterized in that the lower alkyl radicals of the N-neoalkanamides 1 to 2 Carbon atoms and the neoalkanoyl group 9 to 11 Have carbon atoms, and that the N-neoalkanamides present in the perfume in an amount of 2 to 30% by weight. 30. Perfume according to claim 29, characterized in that it N-methyl and / or N-ethyl neoalkanamide in one amount contains from 5 to 15 wt .-%. 31. Perfume according to claim 27 to 30, characterized in that that there is at least 1 wt .-% of ester, aldehyde or contains alcohol from the fragrance class. 32. Perfume according to claim 30, characterized in that it Contains N-ethylneodecanamide, while the rest contain 5 to 40 % By weight citronellol, 5 to 30% by weight geraniol and 2 to 40 % By weight is phenylethyl alcohol. 33. Use of a perfume according to claim 27 to 32, in an amount of 0.1 to 10% by weight for a particulate Detergent, soap bar, liquid textile detergent, Cleaning agent for hard surfaces, Shampoo for hair, upholstery and carpets, for floors and furniture polish, for insect repellents, Insecticides or abrasives.