text:
|Publication number
|Publication type
|Application number
|Publication date
|Jul 18, 1995
|Filing date
|Oct 11, 1994
|Priority date
|Aug 8, 1986
|Fee status
|Publication number
|Robert J. Steltenkamp
|Original Assignee
|Colgate-Palmolive Co.
|Export Citation
|BiBTeX, EndNote, RefMan
|Patent Citations (10), Non-Patent Citations (3), Referenced by (6), Classifications (51), Legal Events (5)
|External Links: USPTO, USPTO Assignment, Espacenet
This application is a continuation of Ser. No. 07/969.904, filed Nov. 2, 1992, now abandoned, which is a continuation of Ser. No. 07/657,707, filed Feb. 19, 1991, now U.S. Pat. No. 5,182,305, which is a continuation-in-part of my U.S. patent application Ser. No. 07/612,747, filed Nov. 13, 1990, now U.S. Pat. No. 5,182,304, Ser. No. 07/267,141, filed Nov. 4, 1988, now U.S. Pat. No. 5,006,562 Ser. No. 07/609,290, filed Nov. 5, 1990, now abandoned, Ser. No. 07/264,936, filed Oct. 31, 1988, now U.S. Pat. No. 5,015,665, Ser. No. 07/071,305, filed Jul. 16, 1987, now U.S. Pat. No. 4,804,683, and Ser. No. 06/894,985, filed Aug. 8, 1986, now abandoned.
This invention relates to N-monosubstituted neoalkanamides wherein the substituent on the nitrogen is cyclic, such as aryl or cycloalkyl, which are novel chemical compounds that possess significant insect repelling properties. More particularly, this invention relates to such neoalkanamides which are of carbon atom contents in the range of 11 to 14 wherein the neoalkanoyl moiety is of 5 to 8 carbon atoms. The mentioned neoalkanamides, especially N-phenyl neoheptanamide, are effective in repelling insects, such as cockroaches, when applied to areas, locations, items, materials and structures, and to surfaces thereof, to protect them against insect infestation and damage. The present invention also relates to various compositions containing such N-substituted neoalkanamides, which compositions are employed as means for depositing such active compounds onto surfaces to be made repellent to insects, and it also relates to processes of using such compounds and compositions to repel insects.
Although some insects, such as bees, are considered to be useful to man (for plant pollination), many types of insects are classified as pests, and many efforts have been made to eradicate or at least control them. However, although effective poisons have been produced, various insects have developed resistences to them (possibly by "natural selection") and others have been able to detect and avoid poisons. Furthermore, many poisons have undesirable effects on human and other animal life, and therefore uses thereof have often been regulated or forbidden. Some insects, like the common German or house cockroach (Blattela germanica), cannot be eliminated entirely from many areas and therefore, realistically, efforts have been made control them, rather than to eradicate them. Also dead cockroaches left in areas that cannot be reached or cleaned, have been identified as a significant allergen in house dust. Results from recent studies by the National Institutes of Health indicate that 10-15 million people in the United States are allergic to cockroaches. Poisons are ineffective in these situations because dead cockroaches in unreachable areas emit the allergen. An effective repellent is the only feasible means to prevent such allergic reactions and if the repellent is applied to hard to-reach areas it can minimize the presence of dead insect bodies there Mosquito repellents have long been marketed and some chemicals that arc effective in repelling roaches have been discovered. Such chemicals may be applied to surfaces of walls, floors, cabinets, drawers, packages, containers, rugs, upholstery and carpeting, and in potential nesting places for insects, such as inside walls and between floors. Similarly, when such repellents are of low toxicity they may be applied to the human body and onto pets, zoo animals and livestock. However, some such repellent materials are toxic and others are foul smelling and discoloring, which adverse properties can seriously limit their utilities. Many of the useful insect repellents reported in the literature are-teriary amides and of these the one heretofore regarded as the most effective all-purpose insect repellent is N,N-diethyl-m-toluamide, which is often referred to as "DEET". However, the present neoalkanamides are superior to DEET in long lasting effectiveness, e.g. against roaches. Additionally, the invented neoalkanamides are also effective to repel other insects, as well as arachnids, including mosquitoes, black flies, carpenter ants and deer ticks. Except for the N-lower alkyl neoalkanamides described in the previously listed patent applications, of which this application is a continuation-in-part, such as N-methyl neodecanamide and N-methyl neotridecanamide, previously known repellents do not show the same potent and long lasting repellencies. In view of the relatively small number of useful insect repellents known, efforts continue to be made to discover additional repellents which would be of greater repellent actions and of longer lasting effects. Desirably, such compounds also would be of improved physical characteristics, such as of even better aroma, desirable volatility, non-staining character, even lower toxicity, improved stability, greater substantivity to substrates, and repellency against a broader group of insect types.
In accordance with the present invention there are provided insect repellent N-monosubstituted neoalkanamides in which the total number of carbon atoms is in the range of 11 to 14, and is in the range of 12 to 14 when the neoalkanoyl moiety is pivaloyl, and the substituent is a cyclic moiety of at least 5 carbon atoms and fort he substituted phenyl moieties is unsubstituted in the ortho position. At present the most preferred of such compounds for employment as an insect repellent, which is especially effective against cockroaches, is N-phenyl neoheptanamide. Also within the bounds of the invention are detergent compositions (both particulate and liquid), carpet and upholstery shampoos, human hair shampoos, hard surface cleaners, and soap and detergent bars comprising such N-substituted aryl and cycloalkyl neoalkanamide(s). Also useful are solutions and dispersions of such neoalkanamide(s) in liquid media or such neoalkanamides dispersed in a particulate or powdered carrier, which liquid or particulate products are suitable for application to an area, location or item from which insects are to be repelled. Also included in the invention are processes for repelling insects by applications of insect repelling amounts of the N-substituted neoalkanamides of this invention to or near a surface, area, location or item from which such insects are to be repelled. In some situations the present repellents may be used in conjunction with insecticides, to repel the insects from one area and toward the location of the insecticide. They may also be formulated with insecticides so that after the repellent effect is lost the treated area will still not be safe for insects. Additionally, compositions containing mixtures of the present repellents with other insect repellents are within the invention, as are mixtures of the invented neoalkanamides.
Computer and manual searches of the prior art have not resulted in the finding of any reports of N-cyclic substituted (such term is considered to be generic to both aryl and cycloalkyl) secondary neoalkanamides of this invention and no analogous N-cyclosubstituted amides were recognized to be useful as insect repellents. Such searches indicated that applicant's N-aryl and N-cycloalkyl neoalkanamides are novel and unobvious. The closest compounds to such N-cyclosubstituted neoalkanamides of this invention appear to be those described in U.S. Pat. Nos. 4,682,982 and 4,715,862, of Steltenkamp and Camara, in U.S. Pat. No. 4,804,290, and in U.S. patent application Ser. Nos. 07/612,747, now U.S. Pat. No. 5,182,304, 07/609,290, now abandoned, 07/267,141, now U.S. Pat. No. 5,006,562, 07/264,936, now U.S. Pat. No. 5,015,665, and 06/894,985, now abandoned, all of Steltenkamp, all of which applications have been cited as parents. However, the neoalkanamides described in the first two of the mentioned patents are employed as anti-static agents, not as insect repellents. In Ser. Nos. 07/354,545, now abandoned, and 06/894,983, now abandoned, of Steltenkamp and Eaton, N-lower alkyl neoalkanamides are utilized as components of perfumes. All such patents and applications (and especially those relating to insect repellents) are incorporated herein by reference.
The N-cyclosubstituted secondary neoalkanamides of this invention include those wherein the cyclic substituent is cycloaliphatic or aromatic, and preferably the cyclic moiety is a hydrocarbon (or hydrocarbyl). The neoalkanoyl moiety may be of to 8 carbon atoms and the aryl moiety, including any substituents thereon, which are preferably lower alkyl(s) of 1 to 3 carbon atoms, desirably in meta positions only (with none in the ortho positions and often also with none in the para position, either), will be of 5 to 9 carbon atoms. Among the cyclic substitutents that may be on the amido nitrogen are included cyclopentyl-, alkylcyclopentyl cyclohexyl-, alkylcyclohexyl, cycloheptyl- and alkylcyclopheptyl. The total number of carbon atoms in the N-substituted neoalkanamide, for good insect repellency, will be in the range of 11 to 14, with the proviso that when the neoalkanoyl moiety is pivaloyl that range is 12 to 14. Of the N-cyclosubstituted neoalkanamides of this invention the substituted neoheptanamides are preferred because they have been shown to be of longer lasting effectiveness in repelling insects from treated surfaces and areas, with N-phenyl neoheptanamide being 90% effective (the standard employed) against cockroaches for at least 25 days, by probit analysis.
The N-cyclosubstituted (or N-cyclic, for short) neoalkanamides may be made from the appropriate neoacids, such as pivalic acid, neohexanoic acid, neoheptanoic acid or neooctanoic acid or appropriate mixtures thereof, or the corresponding acid halides, such as the acid chlorides, may be employed. The amides are easily produced by reaction of such acid or acid chloride with the appropriate amine, such as aniline or 3-methyl toluidine. Pure neoalkanamides of the types described may be made but often the commercial or technical grade acids, which may be used, and the amides made from them, will be mixtures.
The invented amides are of the formula ##STR1## wherein R, R' and R" are alkyl groups, the sum of the carbon atoms contents of which is in the range of 3 to 6, and R"' is cyclic (cycloaliphatic or aromatic) of 5 to 9 carbon atoms, and the carbon atoms content of the amide is in the range of 11 to 14, with the provisos that when the neoalkanoyl moiety is pivaloyl the carbon atoms content will be at least 12 and when an aromatic moiety is substituted such substitution will not be in an ortho position, and preferably will be in meta position(s) only. Further details with respect to R, R' and R" will be given later, in conjunction with a description of neoalkanoic acids which may be employed as starting materials for the production of the neoalkanamides.
Infrared absorption spectra for some representative and preferred N-cyclosubstituted neoalkanamides of this invention are shown in the drawing, in which:
FIG. 1 is an infrared spectrograph of a sample of N-phenyl neoheptanamide, which is more preferred; and
FIG. 2 is an infrared spectrograph of a sample of N-(3-methylphenyl) neoheptanamide.
Both such N-substituted neoalkanamides are considered to be representative of the various other of the N-cyclic neoalkanamide insect repellents of this invention.
To make the neoalkanamides of this invention neoalkanoyl chloride reactant is slowly reacted, with mixing, with the appropriate primary cyclic amine, in a suitable medium, such as ethyl ether, hexane and/or water, producing the amide and hydrochloric acid, and the extent of reaction is monitored by infrared analyses of the reaction mix for presence of the acid chloride. Sodium hydroxide, triethylamine or other material capable of reacting with any hydrochloric acid produced as a result of the reaction that produces the neoalkanamide, may also be present to react with any excess of HCl, and thus drive the reaction. When the neoalkanoyl chloride has been completely consumed mixing is halted and the product is treated with solvent (hexane) and washed with dilute aqueous HCl twice. Then the organic medium, which is about neutral, is separated from the aqueous medium, is then dissolved in the minimum proportion of methanol and is crystallized from it by addition of cold water. The crystals are filtered off and are vacuum dried or they may be recrystallized. The reaction product obtained is water white to light amber in color and is essentially pure. In an alternative method, the neoalkanoic acid may be reacted directly with the lower alkylamine.
Neoalkanoic acids, such as neoheptanoic acid and pivalic acid, are available from Exxon Chemical Americas, and such have been manufactured by reacting a suitable alkene, such as isobutylene or a branched C6, C7 or C8 alkylene feedstock , with carbon monoxide, under high pressure at elevated temperature, in the presence of aqueous acidic catalyst (Koch reaction). The general mechanism involved includes generation of carbonium ion, followed by complexation with carbon monoxide and the catalyst to form a "complex", which is subsequently hydrolyzed to generate the described free acid. The formula of the free neoalkanoic acid is ##STR2## In such neoalkanoic acids and in the neoalkanamides made from them or their acid chlorides R, R' and R" will be methyl in the pivalamides but will include one replacement ethyl for the neohexanamides and a replacement propyl (or isopropyl) or two replacement ethyls for the neoheptanamides. The neooctanamides may include three replacement ethyls or a replacement propyl (or isopropyl) and a replacement ethyl. Neoalkanoic acids mentioned herein and methods for manufacturing them are described in a bulletin entitled NeoAcids Properties, Chemistry and Applications (copyright 1982), Exxon Chemical Americas, hereby incorporated by reference. Acyl chloride starting materials for reactions to produce the invented neoalkanamides may be made from the neoalkanoic acids and suitable chlorating agents, such as phosphorus trichloride, and may be available from Lucidol Division of Pennwalt, Inc. and from White Chemical Corp.
Although it is possible for the insect repellents of this invention to be incorporated in various materials when such materials are being manufactured, as by being mixed in with pulp for making paper, rubber and synthetic organic polymeric plastic batches, and chips for the manufacture of pressed boards, and while the invented insect repellents may also be injected or otherwise inserted into the bodies of items to be made insect repellent, usually the insect repellents will be applied to surfaces of areas, structures or items to be made insect repellent, either by direct application of the insect repelling N-cycloalkyl or aryl neoalkanamide, in liquid solution or dispersion, or dispersed in a powdered carrier, or in a detergent composition, such as a laundry detergent, floor or wall cleaner, upholstery or rug shampoo, hair shampoo, liquid soap, bar soap, or in any other appropriate composition in which it may be usefully incorporated. Among such other appropriate compositions may be mentioned insecticidal and antibacterial washes or dips for humans, pets and farm animals, furniture polishes and finishes, floor waxes and finishes, ointments, salves and topical medicaments, insecticides, fungicides, bactericides, plant fertilizers, mulches and plant potting preparations, to name only a few. In some instances means will be provided for recharging such items and compositions with the active neoalkanamide component to renew the insect repellent effects. In the majority of instances the invented compositions will be applied directly or indirectly by external application to surfaces to be treated, and afterward such application will be made on a continuing basis to maintain a satisfactory degree of insect repellency. Thus, an insect repellent N-cycloalkyl or N-aryl neoalkanamide, such as N-phenyl neoheptanamide, may be painted onto a surface to be treated or it may be applied to such surface washing it (preferably without subsequent rinsing) with a detergent composition containing the active insect repellent. The invented compounds are usually relatively low melting solids or liquids or an in pasty condition at normal ambient temperatures and are water insoluble, so they tend to be relatively substantive to surfaces from detergent compositions and from other preparations, even if such compositions are rinsed off (although rinsing is often better omitted) and normally, after either direct or indirect application to such surfaces, a sufficient amount of the neoalkanamide should remain to be effectively insect repelling, while different application rates of the different neoalkanamides of this invention are desirably used for effective repelling of different insects from different surfaces under different conditions, it is generally considered that insect repellent effects are obtainable at surface concentrations of the active ingredient in the range of 0.002 to 100 g./sq. m. For economic reasons and for effectiveness against more insects there will normally be applied 0.1 or 0.2 to 10 g./sq. m., preferably 0.5 to 2 g./sq. m., e.g., 1 g./sq. m., when roach repellency is desired. Higher application rates, such as 10 to 100 g./sq. m., can be used against other insects, such as mosquitoes, and sometimes also against roaches.
Because the present insect repellents are sufficiently volatile their presences can be detected by insects in the air near a surface to which they have been applied, although evidence indicates that their efficacies are greatest as contact repellents. Therefore, not only are the surfaces repellent to insects, which wi avoid having their body parts contact such surfaces, but the vapors from the N-cyclic neolakanamides will tend to repel insects from th surrounding space. Thus, the application of the volatile repellent to walls of a china closet can repel roaches from the closet interior thereby preventing them from contacting, soiling and contaminating contained dishes, utensils and silverware. Similarly, coating of pantry surfaces, interior and/or exterior, with a furniture polish containing an invented sufficiently volatile repellent, or use of shelf paper containing such a repellent neoalkanamide can discourage roaches from entering the pantry and contaminating foods contained therein. Also, applying an invented neoalkanamide to clothing or washing clothing with detergent compositions containing an invented repellent may prevent insects from lighting on the clothing and its wearer, and from stinging or biting the wearer. Shampooing of a rug with a rug shampoo or carpet cleaner containing the invented repellent will discourage insects from entering the room and from nesting and laying their eggs in or under the rug. Washing of floors and walls with insect repellent detergent compositions formulated for such purpose, especially such compositions which are not to be rinsed off, will deposit thereon a substantive coating of the invented insect repellent and will discourage insects from contacting the floor and wall surfaces and from entering the treated rooms. It is an important feature of the invented insect repellents that although they are sufficiently volatile to be effective, their repellent properties are persistent because they do not evaporate quickly, often lasting as long as a month or more (even longer if incorporated interiorly in a product). The invented repellents may be formulated with insecticides, Such as by being sprayed onto the surfaces of insecticidal powders, e.g., boric acid powder, which is effective against roaches, By use of the neoalkanamide-boric acid composition immediate effectiveness in repelling the roaches is obtained and subsequently, after the repellent activity may have diminished, due to exhaustion by volatilization, any roaches that return to the area may be killed by the insecticide. It is recognized that a more normal practice is to incorporate an attractant with an insecticide but repellent-insecticide compositions also have utility.
It is apparent from the foregoing brief description that the invented insect repellents can be used in many compositions and can be applied in diverse ways. However, among the most useful products which can incorporate the invented neoalkanamides are detergent compositions, from which the neoalkanamides may be surprisingly substantive to the surfaces of washed items. Such detergent compositions operate in several ways to counter insect contamination of the washed item. They remove any earlier contamination, remove stains and soils, on which the insects might feed, and which could attract them, and leave behind the insect repelling neoalkanamide.
The primary component of the present detergent compositions, other than the insect repelling neoalkanamide, is an organic detergent material. Such material may be one of the soaps, preferably a sodium and/or potassium higher (C10-18) fatty acid soap, but is preferably a synthetic organic detergent, which may be of a anionic, nonionic, amphoteric, ampholytic, zwitterionic or cationic type, or may be a mixture of two or more detergents within one or more of such classifications. Preferably, the detergent will be a synthetic organic detergent of the anionic or nonionic type and often the anionic detergents will be most preferred. Descriptions of many such detergents are found in the well known text Surface Active Agents and Detergents, Vol. II, pages 25-138, by Schwartz, Perry and Berch, published in 1958 by Interscience Publishers, Inc. Such compounds are also described in a 1973 publication by John W. McCutcheon, entitled Detergents and Emulsifiers, and in subsequent annual issues of such title. Such publications are hereby incorporated by reference.
The anionic detergents employed may be any such suitable detergents (or soaps), but normally will be salts of alkali metals, such as sodium or potassium, or ammonium or lower alkanol-ammonium salts, e.g., triethanolamine salts. The anionic detergent may be a sulfate, sulfonate, phosphate or phosphonate or salt of other suitable detergent acid but usually will be a sulfate or sulfonate, which together may be designated as "sulf(on)ate". The anionic detergents will include a lipophilic group, which will normally have from 10 to 18 carbon atoms, preferably in linear higher alkyl arrangement, but other lipophilic groups may be present instead, preferably including 12 to 20 carbon atoms, such as branched chain alkyl benzene. In some cases the anionic detergents may include poly-lower alkoxy groups, as in ethoxylated higher fatty alcohol sulfates, e,g., triethoxylated lauryl alcohol sulfate. Normally the number of ethoxy groups in such detergents will be in the range of 1 to 30, preferably 1 to 10. As examples of suitable anionic detergents there may be mentioned: higher fatty alcohol sulfonates, such as sodium tridecyl sulfonate; sodium linear alkyl benzene sulfonates, e.g., sodium linear tridecylbenzene suflonate; olefin sulfonates; paraffin sulfonates; and dioctyl sulfosuccinates. All of the anionic detergents will preferably be sodium salts for most of the particulate detergent compositions of this invention but potassium, ammonium and triethanolammonium salts may be more desirable for some liquid compositions. Usually the detergent will preferably include a lipophilic alkyl moiety of 12 to 16 carbon atoms, often preferably of or averaging 12 to 13 carbon atoms, and preferably such alkyl will be linear.
The suitable nonionic detergents will normally be condensation products of lipophilic compounds or moieties and lower alkylene oxides or polyalkoxy moieties. Highly preferable lipophiles are higher fatty alcohols of 10 to 18 carbon atoms but alkyl phenols, such as octyl and nonyl phenols, may also be used. The alkylene oxide of preference is ethylene oxide and, normally from 3 to 30 moles of ethylene oxide will be present per mole of lipophile, but some such alkoxies may be propoxy and/or butoxy and/or isobutoxy.
In preferred embodiemnts of the invented detergent products, the built detergent compositions, in which builders are employed to improve the detergency of the synthetic organic detergent (or soap), there will be present a building proportion of a suitable builder. Builders used may be inorganic or organic, water soluble or water insoluble, or any mixtures thereof. Among such classes of builders may be mentioned water soluble inorganic salts, including: polyphosphates, e.g., sodium tripolyphosphate; carbonates, e.g., sodium carbonate; bicarbonates, e.g., sodium bicarbonate; borates, e.g., borax; and silicates, e.g., sodium silicate; water insoluble inorganic builders, including zeolites, e.g., hydrated Zeolite 4A; and water soluble organic builders, including titrates, gluconates, NTA, and polyacetal carboxylates. In some cases, as when mildness of the product to the human body or to delicate fabrics is important, alkaline builders and other "harsh" builders will be avoided, and in some cases no builders will be present at all.
Various adjuvants may be present in the detergent compositions of this invention to improve various characteristics of such products. Thus, for example, bentonite may be employed as a fabric softener, perfumes and colorants may be added for their aesthetic effects, soil anti-redeposition agents may be employed, such as sodium carboxymethyl cellulose, and solvents or co-solvents may be present, as in liquid compositions. Among other adjuvants there may be mentioned fluorescent brighteners, antistatic agents, antibacterial agents, fungicides, foaming agents, anti-foams, flow promoters, suspending agents, antioxidants, anti-gelling agents, soil release promoting agents, stabilizers and enzymes.
The detergent compositions of this invention may be in particulate, powder, tablet, bar, liquid, paste, gel, capsule, leaf, foam or "aerosol" or other suitable form, as may be best suited for the purpose intended. Methods for manufacturing products in such forms are well known in the art of processing soaps and detergents, and need not be further mentioned here.
While it is possible to apply the present insect repellin N-cycloalkyl and N-aryl neoalkanamides directly to surfaces and items to be made insect repellent, it is often more convenient and also more efficacious to utilize the repellent neoalkanamide as a liquid solution, emulsion or dispersion, or as a particulate or powder product. To make such solutions the neoalkanamide may be dissolved in any suitable solvent, such as a lower alcohol, e.g., ethanol, or an aqueous alcoholic medium. Of course, other solvents may also be employed, such as hydrocarbons, esters, ketones, aldehydes and halogenated hydrocarbons. Among the hydrocarbons and halogenated hydrocarbons there may be mentioned isobutane, other lower hydrocarbons and the chlorofluorinated lower hydrocarbons, such as dichlorodifluoromethane, monofluorotrichloromethane and other chlorofluoro-methanes, -ethanes and -propanes. Such compounds include the liquefiable gases, which can be maintained in liquid state in pressurized dispensing containers, for ready application, as sprays or in other suitable forms, to locations which are to be made insect repellent. The invented neoalkanamides may also be in aqueous or other emulsion form, when a suitable emulsifier, hydrotrope or surface active agent is utilized, too. Such neoalkanamides may also be dispersed in particulate or powdered inert or active materials. Among such inert materials may be mentioned silica, calcium carbonate, clay, expanded polystyrene, wood chips and sawdust. Also, the neoalkanamides may be dispersed in active materials, such as detergent composition beads, bentonite (a fabric softener) and boric acid (a roach poison).
Other modes of use of the invented insect repellents, some of which have already been mentioned, include incorporation in materials which are intended for use at or near sites from which the insects are to be excluded. Thus, the repellents may be incorporated in shelf papers, wallpapers, wallpaper glues, rugs and carpeting, and carpet padding. They may be formulated in floor waxes, furniture polishes and other preparations that are intended for applications to surfaces in the areas to be treated. They may be automatically dispensed in certain areas, such as storerooms and warehouses, by timer-operated sprayers or other dispensers, and they may be renewably charged to containers, from which they may be vaporized, such as absorbers and other holders, which may be attached to under sides of garbage can covers or may be concealed in wall mounted "vaporizers".
The detergent compositions of this invention, including those that are useful for washing hard surfaces, such as floors, and also soft surfaces, such as those of carpets, laundry, and human hair, will include an insect repelling proportion of N-cycloalkyl or aryl neoalkanamide or a mixture of such neoalkanamides, which proportion is sufficient so that enough of the neoalkanamide is retained on the washed surface, after washing of it with the detergent composition, to repel insects from such surface, and such detergent composition will also include a detersive proportion of soap or synthetic organic detergent (or any suitable mixture thereof). The neoalkanamide is preferably one wherein the cyclic substituent is aromatic, e.g., phenyl or alkylphenyl, but may also be cyclohexyl, substituted cyclohexyl, cyclopentyl, cylcoheptyl or alkyl or other derivative thereof. As was previously mentioned, the cyclic substituent will be of 5 to 9 carbon atoms and the neoalkanoyl moiety will be of 5 to 8 carbon atoms, with the total carbon atoms content being 11 to 14, except for the pivalamides (or trimethyl acetamides), wherein at least 12 carbons should be present. Such carbon atom contents may be those for pure compounds or averages for mixed neoalkanamides.
In particulate built laundry detergent compositions of the invention the active detergent component will usually be synthetic organic detergent selected from the group consisting of anionic, nonionic, amphoteric, ampholytic, and zwitterionic detergents and mixtures thereof, and the builder will be water soluble inorganic or organic builder or water insolubleinorganic builder. The proportions of synthetic organic detergent(s), builder(s), and neoalkanamide(s) to make an effective insect repellent particulate synthetic organic detergent composition will be 1 or 5 to 35%, 10 to 90%, and 0.2 to 10%, respectively. Preferred compositions of such type will have the synthetic organic detergent selected from the group consisting of anionic and nonionic detergents, and mixtures thereof, may contain water soluble filler salt(s), such as sodium sulfate, and will contain a N-aryl or N-cycloalkyl neoheptanamide, such as N-phenyl neoheptanamide or N-(3-methylphenyl) neoheptanamide or a mixture thereof. The proportions of such components for best effects in floor cleaning compositions and other cleaners for hard surfaces will often desirably be 1 to 30% of synthetic organic detergent, 10 to 50% of builder, 0 to 50% of filler and 0.2 to 10% of the repellent.
When liquid detergents containing the invented insect repellent neoalkanamide(s) are made, the same components may be used, plus a liquid medium, but the detergent will preferably be non-soap. Sometimes a conventional emulsifying agent, such as an Emcol�, sold by Witco Chemical Co., Inc., will be employed, in emulsifying proportion. Also, hydrotropes, such as sodium toluene sulfate, and other functional and aesthetic adjuvants, such as have been employed in liquid detergent compositions, and/or fillers, may be included, or not. In the built liquid detergents the synthetic organic detergent content will be in the range of 2 to 25%, the builder content will be in the range of 5 to 40%, the neoalkanamide content will be in the range of 0.2 to 10%, and the liquid medium content, preferably aqueous, will be in the range of 40 to 90%. More preferably, the built liquid detergent compositions of the invention will comprise 3 to 20% of a synthetic organic detergent which is anionic and/or nonionic, 10 to 30% of builder salt(s) for such detergent(s), which may be water soluble, such as potassium pyrophosphate, sodium carbonate, or sodium polyacetal carboxylate, and/or water insoluble, such as sodium zeolite, 0 to 20% of water soluble filler salt, such as sodium sulfate, 0.5 to 5% of one or more of a previously named N-aromatic or cycloalkyl neoheptanamide or other suitable neoalkanamide of the invention, and 50 to 90% of water, preferably deionized water.
When an insect repelling shampoo for use on upholstery, rugs and carpets is to be made, it may comprise 1 to 35%, preferably 5 to 20%, of a detergent selected from the group consisting of water soluble soap(s) and synthetic organic detergent(s), 0 to 40% of builder(s) for the soap and/or detergent, often preferably 0%, and 0.2 to 10% of N-aryl or N-cycloalkyl neoalkanamide, preferably 0.5 to 5%, all being of the types previously mentioned, in a liquid medium, preferably aqueous, the percentage of which may be in the range of 40 to 90%, preferably 70 to 90%, with water being 50 to 90% of the composition, preferably 70 to 90%. Alternatively, the shampoo may be in gel, paste or powder form.
When the present insect repellents are used in shampoos intended for washing human hair on the head and for making the hair repellent of insects, the shampoos will preferably comprise 2 to 25% of soap and/or the previously described synthetic organic detergent(s), and 0.2 to 10% of N-aryl or N-cycloalkyl neoalkanamide, in an aqueous medium, such as 40 to 90% of water, preferably deionized water. The aqueous medium may include up to half thereof of a cosolvent, such as a lower alkanol, e.g., ethanol, or a glycol, but normally the percentage of such cosolvent will be limited to 5 to 20% of the final product. In more preferred embodiments of the shampoos for human hair, there will be present 5 to 22% of synthetic organic detergent, 0 to 20% of water soluble filler salt, 0.5 to 5% of N-aryl or N-cycloalkyl neoalkanamide or mixture thereof, preferably N-phenyl neoheptanamide, N-(3-methylphenyl) neoheptanamide or N-(4-methylphenyl) neoheptanamide (of which the first is most preferred), and 50 to 90% of water, preferably deionized.
Solid or bar or cake insect repellent detergent products can also be made, which may be used for washing persons, animals, laundry, rugs, and/or hard surfaces, such as walls and floors, to make them insect repellent. Such products can comprise "N-cyclic neoalkanamide" (which term will henceforth be used to signify N-aryl neoalkanamides and N-cycloalkyl neoalkanamides) repellent with soap and/or synthetic organic detergent, or may also include builders, fillers and other adjuvants, previously referred to herein. The proportion of N-cyclic neoalkanamide in such products will normally be from 0.2 to 10%, and that of the detersive material will be from 15 to 95%. Such bars will normally be of a moisture content in the range of 2 to 20% and the balance will be of builder(s) and/or filler(s) and/or adjuvant(s), when such are present, Normally, the adjuvant(s) content of the various detergent products will be in the range of 0.5 to 20%, total, with individual adjuvants being in the range of 0.1 to 5%, in most cases.
The various detergent compositions described above may be prepared by processes that are well known in the art and need not be described at length herein. Such processes include spray drying, dry mixing, spray applying and/or coating, agglomerating, sequential dissolving and/or dispersing and/or emulsifying, milling, plodding and pressing.
When the invented insect repellent is to be sprayed or applied in a carrier, such as a liquid or particulate material or medium, the concentration of it therein will be an insect repelling proportion, so that when applied to a surface of a material to be treated (or into the interior or other portion thereof) by spraying, dusting, rubbing, wiping, pouring, depositing or other mechanism, the repellent applied will be in such quantity and/or concentration that it will be effective in repelling insects or a particular type of insect, so that such insect(s) will stay away from the treated location. Such repelling is due to the insect being reluctant to contact the repellent and also in some measure is due to the repellent effect of the vapor from the repellent, which is at least partially volatile, although it may last for as long as a month or more, as normally applied, using the application concentrations that were previously given. The staying power of the repellent may be increased by formulating it with a less volatile carrier, such as a paraffin wax or petrolatum, and when that is done one may find it desirable to increase the amount of the N-cyclic neoalkanamide present (within the ranges previously recited) to ensure that enough will volatilize to be effectively insect repellent. Also, the repellent lasting power is increased when it is incorporated in the body of an article, such as in a mattress or absorbent sponge, rather than only on a surface that is exposed to the air (and again, one may wish to employ more of the invented repellent in such cases).
The concentration of the repellent chemical(s) in a liquid medium, such as an aqueous medium, in which a dispensing agent or emulsifier may be employed, too, will often be in the range of 0.5 to 10%, e.g., about 1% or 5%, for roach repellency. The liquid medium may be water, lower alkanol, such as ethanol, lower ketone, such as acetone, lower hydrocarbon, such as isobutane, cyclopropane or mixture thereof, or halogenated lower hydrocarbon, such as chlorofluorinated, fluorinated or chlorinated lower hydrocarbons, e.g., Propellants 11 and 12. The Various "lower" compounds are of 1 to 4 carbon atoms per molecule, preferably 1 or 2 carbon atoms, and in the case of those that are normally in the gaseous state, they are under sufficient pressure to maintain them in liquid state.
Similar concentrations of the invented repellents may be employed in powdered or particulate carriers. Thus, the invented neoalkanamides may be applied, as by spraying of liquid droplets, onto powdered calcium carbonate, silica, clay or boric acid, onto grains of such materials, or onto detergent composition particles or synthetic organic polymer beads (preferably of particle sizes between 125 microns and 2.4 mm. in diameters), in concentrations in the range of 0.2 to 0 or 25%, preferably 0.5 to 5 or 10%, for roach repellents.
In insect repelling processes or treatments in which the invented repellents are employed they will normally be applied to surfaces to be treated at concentrations such that 0.002 to 100 g./sq. m. initially remain on such surfaces after treatment, with such application rate preferably being 0.01, 0.1 or 0.2 to 5 or 10 g./sq. m. and more preferably 0.5 to 2 g./sq. m., e.g., 1 g./sq. m. for most effective and efficient action against roaches. Concentrations outside such ranges may sometimes also be of at least partial effectiveness. When the repellent is in a detergent composition which is employed in an aqueous washing medium, such as water, the wash water will usually contain from 0.05 to 5 or 10% of the detergent composition, but in some applications, such as shampooing of human hair or of carpets or rugs with foam preparations, the concentration may be greater, sometimes being as high as 25%.
When the repellents are incorporated in and applied to surfaces in other media or preparations, such as waxes or furniture polishes, the concentrations thereof will usually be in the same ranges as for detergent compositions, but may be increased, if desired, in some such instances to as high as 25%.
The invented repellents possess various significant advantages over various other repellent materials available. Like the N-lower alkyl neoalkanamides they are essentially non-toxic and therefore are not hazardous to children or pets that might come into contact with them, after application. They are pleasantly aromatic and therefore do not usually adversely affect the aromas of preparations into which they are formulated. They are substantially colorless and therefore can be employed in detergents, shampoos, polishes, sprays, and various compositions and preparations wherein the imparting of color would not be acceptable. They are effective both as contact and vapor repellents and are superior in repelling action to various commercial insect repellents, especially against German cockroaches, which are considered to be the most difficult household insect pest to control. The present repellents are long lasting, with tests having shown some of them, especially N-phenyl neoheptanamide, to be effective to repel roaches for more than three weeks after topical application. They are also considered to be effective repellents against mosquitoes (Anopheles quadrimaculatus and Aedes aegypti). They are sufficiently stable to be able to maintain their insect repelling properties despite being incorporated in various soap, detergent, polish, wax, insecticide, cosmetic, and coating preparations, in liquid, paste, gel, foam, powder, particulate or solid bar form, or in aqueous or other solvent solutions, emulsions or dispersions, and they are substantive to surfaces to which they are applied from such media.
Experimental work to date has proven conclusively that members of the class of the invented N-cyclic neoalkanamides are superior insect repellents, being especially effective against the common household pest, the German cockroach, and evaluations of such compounds indicate that they will also be effective repellents against other insects, such as those in the group of flies, fleas, lice, mosquitoes, bees, wasps, hornets, ants, beetles and other roaches, such as the American cockroach, and against arachnids, such as spiders, ticks and mites. Because to date data on N-cyclic neoheptanamides are the most complete and are very convincing of the superior insect repelling activity of such N-cyclic neoalkanamides against German cockroaches, and because such data were obtained from controlled tests, conducted in connection with entomological research at a major university, such data will constitute the primary insect repellency results that will be reported in the examples given below.
The following examples illustrate but do not limit the invention. Unless otherwise stated, all parts are by weight and all temperatures are in � C.
N-(3-methylphenyl) neoheptanamide was made from m-toluidine and neoheptanoyl chloride (which can be made by chlorinating neoheptanoic acid with PCl) in a reaction conducted in a glass flask equipped with a stirrer, a thermometer and an addition funnel (a dropping funnel), and connected to a condenser equipped with a Drierite� desiccant tube. The flask was placed in an ice bath and was charged with 90.8 grams of m-toluidine, and 85.7 grams of triethyl amine (which functioned to remove from the reaction mixture any HC1 that was produced.). Then 109.8 grams of neoheptanoyl chloride (obtainable from Pennwalt's Lucidol Div.) were added dropwise to the flask, while mixing was continued, with intermediate additions of 300 ml. portions of distilled water (after 30 minutes) and hexane (after an additional five minutes). Samples were analyzed for acid chloride content by infrared absorption analysis and the reaction was considered complete and mixing was discontinued after 75 minutes, when all the neoheptanoyl chloride had been added and no acid chloride remained in the mix. After such completion of the reaction the flask contents were allowed to come to room temperature. The mixture was then transferred to a 6-liter separatory funnel with the aid of another 300 ml. of hexane and was washed twice with dilute aqueous HCl to a pH of 6.5, to separate the N-(3-methylphenyl) neoheptanamide from the triethyl amine chloride, after which the hexane layer was drawn off and the solvent was evaporated off. The resulting product was then dissolved in 300 ml. of methanol (about the minimum amount needed for solution) and two liters of cold distilled water were added to such solution, with stirring, which resulted in precipitation of solid N-(3-methylphenyl) neoheptanamide. Such was filtered out from the accompanying liquid and was dried under vacuum. The resulting product was obtained in 68% yield. After recrystallization it was found to have a melting point of 62�-64� C. Its infrared transmission spectrum is shown in FIG. 2.
N-phenyl neoheptanamide, of a melting point of 64.65� C., made in the same manner as described above, with the only changes in the procedure being in the use of 0.85 g. mole of aniline (79 g.) instead of 0.85 g. mole (90.8 g.) of m-toluidine. The product, N-phenyl neoheptanamide, is obtainable in about 70% yield (it is expected that yields will approach 90% as the process is improved further), with the product being at least 95% pure (99% purity is obtainable, but is not usually cost efficient), like the purity of N-(3-methylphenyl) neoheptanamide, the making of which was described above. The product's infrared spectrograph is shown in FIG. 1.
In reactions like the neoheptanoyl chloride reactions described above in this example other N-cyclic neoalkanamides of this invention are made, including N-phenyl neohexanamide, N-phenyl neooctanamide, N-cyclohexyl neohexanamide, N-cyclohexyl neoheptanamide, N-(3,5-dimethyl) cyclohexyl pivalamide, N-(3-methylphenyl) pivalamide, N-(3-methylphenyl) neoheptanamide, N-(3-ethylphenyl pivalamide, and N-(3,5-dimethylphenyl) pivalamide, using equivalent gram-molar weights of the appropriate cyclic substituted primary amines, triethyl amine and neoalkanoyl chlorides. The products are obtained in essentially the same types of yields and of essentially the same purity as the N-phenyl neoheptanamide and N-(3-methylphenyl) neoheptanamide previously described.
The compounds for which manufacturing methods are described in Example 1 are made but the starting materials which act as sources of the neoalkanoyl moieties are the corresponding neoalkanoic acids instead of the acid chlorides, and no triethyl amine is employed. In such reactions, in which the neoalkanoic acids are reacted with about a 10% excess, over stoichiometric proportion, of the cyclic substituted amines, the reaction is desirably conducted in a closed system and the flask is equipped with a heating mantle, a magnetic stirrer, a source of nitrogen gas with means for conveying it to below the surface of the reaction mixture, and a thermometer and thermostatic control to regulate the temperature of the reaction mixture, which, is held at about 240� C. for about five hours. The reaction products are separated and washed and have solvent removed from them in the same manner as described in Example 1. The products resulting are of infrared spectrographs like those of samples of the corresponding products of Example 1.
The N-(3-methylphenyl neoheptanamide made by the "neoheptanoyl chloride" process of Example 1 was tested for cockroach repellency, using 50 male German cockroaches in the test, which is a modification of the method described by Goodhue and Tissol in J. Econ. Entomol. 45:133-134 (1952). In such modified method two ml. of a 1% solution of the N-(3-methylphenyl) neoheptanamide were applied to the entire inside surface (188 sq. cm.) of an unwaxed 237ml. Dixi� ice cream carton, with two 1.5 cm. diameter holes cut in opposite sides of the cup, at the lip, which deposited approximately 1 g./sq. meter of the N-cyclic neoalkanamide. Control cups were treated with acetone only and both cups were dried in a fume hood for an hour. Both the experimental and control cups were placed at opposite sides of plastic test cages (51�28�20 cm.) to which the roaches had been acclimated by a previous 2-day occupancy. Food and water were available to the roaches between the cups. The side walls of the containers were coated with a Teflon� emulsion to prevent the roaches from climbing them. The test site was kept on an alternating 12 hours light-12 hours dark cycle at 27� C. and midway through each photophase the numbers of roaches resting on the inner walls of each cup were recorded, after which the insects were disturbed and the positions of the cups were reversed. The test continued for 25 days or until an equal number of roaches was found in both cups. By probit analysis the number of days of 90% effectiveness (9 times as many of the roaches in the untreated cup as in the treated cup), which is considered to be a standard for successful repellency, was determined. The more days of 90% or more repellency the better the insect repellent. By this test N-(3-methylphenyl) neoheptanamide was rated over 25 (days 90% or more effectiveness) against male German cockroaches (Blatella germanica). Similar results were also noted for N-phenyl neoheptanamide, with the rating for it being 24.8. Both such N-cyclic neoalkanamides are also repellent of American cockroaches and various other insects and arachnids, including mosquitoes, black flies, carpenter ants and deer ticks. It should be noted that in another testing of N-(3-methylphenyl) neoheptanamide for insect repellency the rating thereof was less than 25 days, so the N-phenyl neoheptanamide may be considered to be the more effective of these repellents.
The other N-cyclic neoalkanamides mentioned in Examples 1 and 2 are also repellent of cockroaches, as can be shown by the laboratory test described. What is even more important is that they are all insect repellents, which is surprising, because all the N-substituted neoalkanamides previously known to be insect repellents were not cyclic or aromatic in structure and it had been thought that they had to be in liquid state, under ambient conditions, to be insect repellent. Furthermore, it is surprising that the present N-cyclic neoalkanamides, in rather narrow total carbon atom content ranges and of certain molecular structures, are effective, while outside such ranges and of different structures (ortho-substituted) aryls are not repellent.
In the described tests results are the same whether the repellents are made by the direct condensation method, from neoalkanoic acids or from neoalkanoyl chlorides.
Instead of applying the repellents to the test surfaces in acetone solution they may be sprayed onto such surfaces by means of "aerosol" or pressurized sprays in a 50:50 mixture of isobutane and cyclobutane or a 60:40 mixture of Freon 12 and Freon 11 (dichloridifluoromethane and trichloromonofluoromethane, respectively) or in other pressurized solvents. Instead of applying the solutions as 1% solutions, as in the tests reported earlier in this example, concentrations in the range of 0.5 to 30% may often be used, depending to some extent on the solubility of the repellents in the solvent system employed, for example, 15% in the Freon system, 20% in the hydrocarbon system, 5% in ethanol, and 25% in methyl ethyl ketone. Aqueous systems may also be used, preferably with emulsifiers or suitable surface active agents being present to hold the repellent in homogeneous suspension as colloidal droplets, with its concentration usually being somewhat lower than for the organic solvent solutions, e.g., 3%, 5% and 7%. All such liquid systems may be applied with the aids of cloths, pads, spray cans and nozzles, or gels or pastes can also be used, and applications may be to test surfaces or to actual areas, locations and items from which insects and arachnids are to be repelled.
In practical tests, on actual kitchen floors, counters, drainboards and walls, and in kitchen cabinets and dishwashers, and under refrigerators, in roach-infested apartments, significantly fewer roaches will be observed on surfaces to which or near which the invented repellents are applied than on control surfaces, and fewer roaches are found on the bottoms and shelves of cabinets and pantries when walls thereof are treated with the invented repellents, especially when the repellent is N-phenyl neoheptanamide, N-(3-methylphenyl) heptanamide or a 50:50 mixture thereof, indicating that the repellents are vapor-effective too, as well as contact-effective. When floors, walls, counters, sinks, cabinets, appliances, windows, doors, rugs and carpets in a house or apartment are treated with preferred embodiments of the invented repellents, e.g., N-phenyl neoheptanamide and/or N-(3-methylphenyl) neoheptanamide, the incidence of cockroach infestation is reduced, compared to control apartments where no repellent is applied. However, because of the initial presence of the pests in the premises, control of them may take as long as a week, a month or more, and sometimes can require several applications of the repellent. In some instances the application rates are desirably increased to as high as 10 g./sq. m. but in other instances such rates may be dropped to 0.01 g./sq. m. or lower. Of course, results are usually better with the higher application rates.
N-(3-methylphenyl) neoheptanamide, dissolved at a suitable concentration, e.g., 10%, in acetone, is applied to a cotton stocking so that 1 g./ of the neoalkanamide is on 280 sq. cm. of stocking. Two hours after treatment of the stocking (during which period the acetone volatilizes off) the stocking is pulled over a previously installed nylon stocking on the arm of a human test subject and that so-covered arm is inserted into a cage of adult mosquitoes of a type against which DEET is an effective repellent. Two such species are Aedes aegypti and Anopheles quadrimaculatus. If fewer than five mosquitoes bite the subject through the stocking during a one-minute exposure the test is repeated 24 hours later, and if fewer than five mosquitoes then bite the subject the test is repeated weekly thereafter until five bites are received within a one-minute exposure period. The degree of repellency of a treatment chemical or composition is measured by the number of days from application of the chemical to the stocking until five mosquitoes bite the test arm within the one-minute exposure period. The described test is an Agricultural Research Service (U.S.D.A.) screening test and is that which is employed by the U.S.D.A. Insects Affecting Man and Animals Research Laboratory, at Gainesville, Fla.
In the described test against Aedes aegypti DEET is rated 22 and N-methyl neodecanamide (MNDA), a standard for N-lower alkyl neoalkanamides, is rated 15, and when the test mosquito is Anopheles quadrimaculatus the ratings are 29 and 36, respectively. The present N-cyclic neoalkanamides such as N-phenyl neoheptanamide and N-(3-methylphenyl) neoheptanamide, are considered to be about equivalent to the DEET and MNDA standards, in mosquito repellency, as may be measured by the described test.
In actual use on the human body, to which they are applied, dissolved in a suitable solvent, in a skin lotion or cream, or in an "aerosol" spray, the N-cyclic neoheptanamides will be about equivalent to DEET, giving at least an hour's protection against Aedes aegypi and Anopheles quadrimaculatus when 0.3 g. is applied to a human forearm. Similar results are obtainable with other N-cyclic neoalkanamides of the types described in Examples 1 and 2.
______________________________________Component Percent______________________________________Sodium linear tridecyl benzene sulfonate 20.0Sodium tripolyphosphate 40.0Sodium carbonate 10.0Sodium bicarbonate 10.0Borax 5.0Enzyme blend (proteolytic + amylolytic in 1.0powdered carrier)Sodium carboxymethylcellulose 0.5Fluorescent brightener 1.0N-(3-methylphenyl) neoheptanamide 2.0Water 10.5 100.0______________________________________
All of the components of the detergent composition except the enzyme powder and repellent are mixed together in a crutcher slurry, which is spray dried to hollow globular bead form, of particle sizes in the range of No's. 10 to 100, U.S. Sieve Series. Subsequently, the enzyme powder is blended with the spray dried beads and the melted insect repellent is sprayed onto the mixture, while it is being tumbled, to form a uniform composition. In place of the N-(3-methylphenyl) neoheptanamide there may be substituted N-phenyl neoheptanamide or others of the previously mentioned N-cyclic neoalkanamides of this invention and an insect repellent detergent composition will result, which can impart insect repellent properties to washed laundry. Also, the proportion of the active insect repellent may be increased to 4%, for example, to improve such insect repellency.
______________________________________Component Percent______________________________________Sodium linear C12-14 alkylbenzene sulfonate 10.0Sodium tripolyphosphate 40.0Sodium carbonate 20.0Sodium sulfate, anhydrous 27.0N-phenyl neoheptanamide 3.0 100.0______________________________________
The detergent, builder and filler powders are mixed together and the N-phenyl neoheptanamide, in melted state, is sprayed onto the powder mix while mixing is continued.
The resulting powder is dissolved in water and is used to wash linoleum, vinyl tile and ceramic tile floors in areas of homes wherein German or American cockroaches had been seen. After repeated washings, without rinsing, over a period of a month, sightings of the roaches are significantly fewer in almost all cases and many times none are seen. However, if such treatment is discontinued the roaches are often seen again. Also, when the cleaner is rinsed off the floor some repellency can be noted, but it is at a reduced level. Similar results are obtainable when the N-phenyl neoheptanamide is replaced in the cleaner formula by N-(3-methylphenyl) neoheptanamide or is used in mixture with it or with N-methyl neodecanamide, using about equal proportions of each such repellent. Also, similar results are obtainable when others of the cyclic neoalkanamides of the invention are employed and when the amounts thereof present are varied within the described range, 0.2 to 10%, so that the amount of the insect repellent applied to the surface treated is in the range of 0.002 to 100 g./sq. m., preferably being in the range of 0.2 to 10 g./sq. m.
______________________________________Component Percent______________________________________Silex (finely divided silica powder) 97.5Sodium linear dodecyl benzene sulfonate 2.0N-phenyl neoheptanamide 0.5 100.0______________________________________
______________________________________Component Percent______________________________________*Nonionic detergent 1.0Sodium linear dodecyl benzene sulfonate 2.0Sodium cumene sulfonate 5.0Sodium carbonate 5.0Sodium bicarbonate 1.0Fluorescent brightener 0.02Dye 0.01N-phenyl neoheptanamide and/or 1.0N-(3-methylphenyl) neoheptanamideWater (deionized) 84.97 100.0______________________________________ *Condensation product of 1 mole of higher fatty alcohol mixture averaging 10 carbon atoms, with 5 moles of ethylene oxide.
______________________________________Component Percent______________________________________Sodium salt of lauric monoethanolamide sulfosuccinate 30.0Mixed lipolytic, proteolytic and amylolytic enzymes 2.0Sodium tripolyphosphate 20.0Sodium hexametaphosphate 5.0Sodium monophosphate 3.5Sodium bicarbonate 20.0Urea 8.0*Micro-Cel � 10.0N-phenyl neoheptanamide 1.5 100.0______________________________________ *Finely divided hydrated synthetic calcium silicate (JohnsManville Products Corp.)
This product should be diluted 1:30 with water before use. One hundred grams will suffice to clean about ten square meters of soiled carpeting.
______________________________________Component Percent______________________________________*Sulframin OBS 10.0Aqueous ammonia (28%) 30.0Water 58.5N-phenyl neoheptanamide 1.5 100.0______________________________________ *Linear alkylaryl sulfonic acid (Witco Chemical Corp.)
Before use this upholstery cleaner is mixed 1:3, by volume, with Stoddard solvent.
______________________________________Component Percent______________________________________Ammonium monoglyceride sulfate 22.0Hydroxypropyl methyl cellulose 1.0Polyacrylamide 1.0N-phenyl neoheptanamide 1.0Deionized water 75.0 100.0______________________________________
______________________________________Component Amount (as indicated)______________________________________Yellow ceresin wax 2.0 ouncesYellow beeswax 2.0 ouncesStearic acid 2.0 ouncesWhite petrolatum 4.0 ouncesWhite mineral oil 8.0 fluid ouncesWater 6.0 fluid ouncesBorax 0.3 ounceTriethanolamine 0.5 fluid ounce______________________________________
The ceresin, beeswax, petrolatum, stearic acid and white mineral oil are melted together by heating to 71� C. The borax is dissolved in hot water and the triethanolamine is added to the solution, with the temperature being raised to 71� C. The aqueous solution is poured into the melted wax mixture with stirring and stirring is continued as the mixture is removed from the heat. When it begins to thicken there are added to it 10 grams of N-phenyl neoheptanamide or N-(3-methylphenyl) neoheptanamide or 5 grams of each of such neoalkanamides.
______________________________________Component Parts______________________________________Glyceryl monostearate 50.0Oleic acid 30.0Mineral oil 15.0Lanolin 10.0Triethanolamine 12.0Sodium lauryl sulfate 10.0Preservative 10.0Water (deionized) 980.0N-phenyl neoheptanamide 12.0______________________________________
______________________________________Component Percent______________________________________*Higher fatty acid soap chips 88.0N-phenyl neoheptanamide 1.0Titanium dioxide 1.0Preservative (stannic chloride) 0.2Water 9.8 100.0______________________________________ *80:20 tallow:coco sodium soap
Instead of soap bars and cakes, soap-synthetic bars can be made by substituting sodium coco-monoglyceride sulfate for up to 25% of the soap content of the formula. Similarly, by employing a suitable plasticizer, all-synthetic detergent bars can be made.
Preservative, titanium dioxide, repellent and some water are milled with the dried soap chips (which contain about 8% water), the product resulting is plodded and the bar made is cut to lengths and pressed to cake shape. Laundry bars can be made by adding 20 to 40% of builder salt, such as sodium tripolyphosphate and/or sodium carbonate to the formula, usually with an increase in the moisture content to improve plasticity during processing. Framed laundry bars and synthetic laundry bars can also be made and the content of the insect repellent will sometimes be increased in such bars, up to about 5%.
______________________________________Component Percent______________________________________*Propellant 12 45.5*Propellant 11 45.5Mineral oil 4.0N-phenyl neoheptanamide 5.0 100.0______________________________________ *dichlorodifluoromethane *trichloromonofluoromethane
The mineral oil and insect repellent are dissolved in the pressurized propellant mixture and such mixture is pressure filled into a dispensing container equipped with a spray nozzle designed for optimum spraying of the repellent solution.
______________________________________Component Percent______________________________________Clay, powdered 99.0N-(4-methylphenyl) neoheptanamide 1.0 100.0______________________________________
______________________________________Component Percent______________________________________Montan based ester wax 6.0Polyethylene wax 4.0Non-oxidized microcrystalline wax 5.0Tall oil fatty acids 0.2Aqueous potassium hydroxide solution (43%) 0.5N,N-diethylaminoethanol 1.0Methyl carbitol 1.0N-cyclohexyl neooctanamide 2.0Water 80.3 100.0______________________________________
______________________________________Component Parts______________________________________Carnauba wax 5.0Beeswax 5.0Ceresin wax 5.0Silicone oil (DC 200) 5.0Stoddard solvent 40.0Sodium soap (75:25 tallow:coco) 2.0Water 130.0______________________________________
A wax-silicone concentrate is made by heating the Stoddard solvent to a temperature of about 52� C. and gradually adding to it the pre-melted waxes and silicone oil with agitation. Concurrently, the soap is dissolved in the water at a temperature of about 90� C., after which the hot soap solution is admixed with the wax dispersion, under vigorous agitation. The mixture is then cooled rapidly to room temperature and 385 parts of water, 71 parts of naphtha and 15 parts of N-(3,5-dimethylphenyl) pivalamide (dissolved in the naphtha) are slowly added to it. 71 Parts of Propellant 12 are then pressure loaded into dispensing containers after pre-loading of the balance of the composition.
Rolls of shelf paper are sprayed on both sides thereof with N-(3-methylphenyl) neohexanamide, dissolved in a volatile solvent (acetone) and are re-rolled after volatilization off of the solvent. The proportion of repellent is regulated to be about 2%, although in some instances as little as 0.1% may be employed. The shelf paper has a long "shelf life" prior to use because loss of the repellent by volatilization is inhibited by the rolling of the paper. In a modification of this example the N-cyclic neoalkanamide repellent is added to the paper pulp during the manufacturing process but care must be taken not to drive off the repellent during any drying operations.
A 2% .concentration of N- {3-methylcyclohexyl) neohexanamide in a sponge is made by injecting the N-cyclic neoalkanamide into the interior of an open celled polyurethane form, of flat cylindrical shape, which is inserted in a perforated holder affixed to the interior of the lid of a "step-on" kitchen waste container.
______________________________________Component Percent______________________________________Boric acid 98.0N-phenyl neoheptanamide 2.0 100.0______________________________________
The various products of Examples 5-21 are all effective in repelling insects, especially German and American cockroaches. However, they represent only a few of the many compositions and articles of manufacture within the present invention,
The invention described herein is a significant one because mankind has long been in need of effective insect repellents and such compounds have been comparatively rare. Also, among the invented compounds are several which are as effective as or more effective than the previously known best commercial repellents. The invention is unobvious because the art prior to this invention and those of the mentioned parent applications did not teach that secondary neoalkanamides would be insect repellents of long lasting effects. Neither does any art teach any equivalence or interchangeability of aromatic or cyclic substituents on such amide nitrogen for insect repellency. In fact, applicant has discovered that such equivalency does not exist, except for some types of compounds. Note that while it is important that the total number of carbon atoms in the insect repellent secondary amide of this invention should be in the range of 11 to 14, even 11-carbon compounds are ineffective if the neoalkanoyl moiety is pivaloyl. If substituents on the ring of the cyclic compound are in ortho position(s), as in N-(2-methylphenyl) neoheptanamide, the compound will be ineffective as a longer lasting insect repellent. Also, while the inventor previously thought that to be effective insect repellents his secondary amides should normally be in liquid state, he has now discovered some normally solid secondary amides that are usefully effective. In short, except for rather closely related compounds of the types described by applicant, it appears that the insect repellency of his described N-cyclic neoalkanamides wasn't generally predictable and hence his described discoveries are unobvious.
The invention has been described with respect to various illustrations and embodiments thereof but is not to be limited to them because it is evident that one of skill in the art will be able to utilize substitutes and equivalents without departing from the invention.
|Cited Patent
|Filing date
|Publication date
|Feb 14, 1977
|May 8, 1979
|Wilkinson Sword Limited
|Acyclic carboxamides having a physiological cooling effect
|Apr 25, 1980
|Oct 20, 1981
|Wilkinson Sword Limited
|Acyclic carboxamides having a physiological cooling effect
|Jun 21, 1988
|Jan 30, 1990
|Fidia S.P.A.
|Organic amide compounds derived from nitrogenous lipids
|Sep 29, 1986
|Feb 20, 1990
|Nelson Research & Development Co.
|Compositions comprising N,N-dialkylalkanamides
|Oct 30, 1989
|Jul 31, 1990
|Eli Lilly And Company
|Feb 19, 1991
|Jan 26, 1993
|Colgate-Palmolive Co.
|N-aryl and n-cycloakyl neoalkanamide insect repellents
|Mar 13, 1980
|Sep 24, 1981
|Henkel Kgaa
|Deodorant cosmetic compsn. e.g. sprays and sticks - contg. alpha-branched alkanoic acid derivs. and opt. antioxidant
|Nov 14, 1985
|May 21, 1987
|Bayer Ag
|Herbicidal composition containing photosynthesis-inhibitor-type herbicide in combination with pivalamides
|Title not available
|Title not available
|Chemical Abstracts 86:139083y (1977).
|Lwowski, W. et al., "Cyclisierung von Alkanoylnitrenen," Justus Liebigs Annalen der Chemie, 1977, pp. 8-19.
|Lwowski, W. et al., Cyclisierung von Alkanoylnitrenen, Justus Liebigs Annalen der Chemie, 1977, pp. 8 19.
|Citing Patent
|Filing date
|Publication date
|Jun 10, 1996
|Mar 11, 1997
|Colgate-Palmolive Company
|Insect repelling compositions comprising mixtures of an N-alkyl neoalkanamide and DEET
|Apr 8, 1998
|Apr 25, 2000
|Collins; Daniel R.
|Method for treating garments with insect repellent
|Sep 10, 1998
|Sep 4, 2001
|Arizona Board Of Regents
|Long-acting, chemical-resistant skin emollients, moisturizers, and strengtheners
|Oct 27, 2005
|Jul 28, 2009
|Georgia-Pacific Chemicals Llc
|Non-aqueous coating formulation of low volatility
|Mar 28, 2008
|Nov 18, 2014
|Contech Enterprises Inc.
|Compounds, compositions and methods for repelling blood-feeding arthropods and deterring their landing and feeding
|Oct 27, 2005
|May 3, 2007
|Georgia-Pacific Resins, Inc.
|Non-aqueous coating formulation of low volatility
|U.S. Classification
|514/629, 564/190, 564/215, 554/35, 514/919, 514/623, 564/204, 564/188, 564/191, 514/625, 564/189, 564/192, 564/217, 514/627, 514/624, 514/628
|International Classification
|Cooperative Classification
|European Classification
|Jan 19, 1999
|Fee payment
Year of fee payment: 4
|Jan 16, 2003
|Fee payment
Year of fee payment: 8
|Jan 31, 2007
|Maintenance fee reminder mailed
|Jul 18, 2007
|Lapse for failure to pay maintenance fees
|Sep 4, 2007
|Expired due to failure to pay maintenance fee
Effective date: 20070718


text:
Verified ID
Email addressVerified
Phone number▒▒▒▒▒▒▒▒▒▒ 77
Reviewed4 Reviews
Offline IDDriver License
About Me
- Work
- ABC Radio,Australia
- Richard's Airbnb Symbol
Hey, I'm Richard!
Darwin, Australia · Member since September 2012
Hi I'm Richard. I am an inveterate traveller, especially thro Asia, Australia, Sri Lanka, America and now Europe from AUG-DEC 2015. I'm a former actor turned radio host with 19 years radio for ABC in Australia- Started in rock station Triple J, now in contemporary music and talk interviews based in Darwin .I lived in Chengdu, China for 2 years where I edited a magazine and worked helping to relocate expatriates. Also did voice overs for Chinese TV /video and radio.Huge music collector-Love a great band, rap, rock,dub,jazz, classical music: I don't care really. An art gallery,cinema, bookshop, restaurant, or late night bar...oh and food - did I mention food?

subset: commoncrawl


text:
11 grieving families at heart of oil spill
NEW ORLEANS (AP) - Nearly two weeks after 11 people died in an oil rig explosion, there's been barely a mention of their names as the catastrophe plays out on a worldwide stage.
Michelle Jones lost her 28-year-old husband, Gordon, in the explosion and says it seems the victims have been forgotten.
She and other victims' family members aren't casting blame; they understand the environmental impact is the reason why the spill has gotten so much attention and their loved ones, so little.
Had it been a plane crash or a tornado strike, grieving families and friends could at least go the place where their loved ones died.
Not so with this disaster. The Deepwater Horizon oil rig was 50 miles south of the Louisiana coast. The final resting place of the 11 -- who came from Louisiana, Mississippi and Texas -- is a watery, inaccessible grave.


text:
Reviewed By Paul P (Tell City, IN) —4/17/2016 5:52 AM
This is my second Rim-Pro-Tec Wheel Shield. Works good
Reviewed By Wayne B (Tiverton, RI) Reviewed for a 2013 Porsche Boxster —2/3/2016 7:54 AM
While I like this brush, I have had issues with the quality of this item in the past. Fortunately Zymol stands behind their products and promptly sent me another one after the head on mine cracked. Other than having to send them the failed item before they would honor their warranty, I rate them favorably. The brush itself is great for getting into those hard to reach areas.
Most car cleaning products are fairly simple to use. But, even still, you want to make sure you're using them properly to get the most effective clean for your car. Check out this article when you want some helpful tips on how to speed shine your car, truck or SUV.
Know before you buy! Read customer reviews about Detailing Tools or ask our Product Experts.


text:
Write a review for a chance to win a $1,000 gift card. See details.
'Swept Off My Feet' Leg & Foot Massage Oil
Product not available
Want a consultation with an expert?
Chat with a beauty stylist or call 1.800.7beauty.
Nourish and protect your legs and feet with Swept Off My Feet leg and foot massage oil by essie. The rich formula is blended with vitamin E and essential fatty acids to help hydrate dry skin.
- 8.4 oz.
- By essie.
Paraffinum Liquidum / Mineral Oil, Isohexadecane, Dimethicone, Isononyl Isononanoate, Brassica Campestris Oleifera Oil / Rapeseed Seed Oil, Prunus Armeniaca Kernel Oil / Apricot Kernel Oil, Hydrogenated Butylene/Ethylene/Styrene Copolymer, Hydrogenated Ethylene/Propylene/Styrene Copolymer, Tocopheryl Acetate, Passiflora Incarnata / Passiflora Incarnata Seed Oil, Parfum / Fragrance, Glyceryl Linoleate, Limonene, Glyceryl Oleate, Rosa Canina Fruit Oil, Linalool, Glyceryl Linolenate, Carrot Oil / Beta-Carotene, Citral (D159199/3).
Ingredients are subject to change at the manufacturer's discretion. For the most complete and up-to-date list of ingredients, refer to the product packaging.
'Swept Off My Feet' Leg & Foot Massage Oil
Write a review for a chance to win a $1,000 gift card. See details.


text:
Kelvin Hughes
Kelvin Hughes Announce Saab AIS Deal
Kelvin Hughes is now able to supply both Automatic Information Systems (AIS) and Voyage Data Recorders (VDR), as part of its fully compliant integrated bridge systems (IBS). Saab Transponder Tech, following an original equipment manufacture (OEM) agreement between Saab and Kelvin Hughes, will supply the AIS. AIS systems are being made compulsory as part of the changes to SOLAS V, which go into effect in July 2002. The systems are designed to work in tandem with a ship's radar system to improve the identification and location of other vessels. Kelvin Hughes had several criteria that were important when selecting a third party AIS supplier including early type approval and hardware availability. This OEM contract enables Kelvin Hughes to supply a complete range of fully compliant hardware for all compulsory equipment onboard new builds or for retrofits. With both AIS and VDRs becoming mandatory for certain vessels under the changes to SOLAS V in July 2002, Kelvin Hughes is perfectly positioned to supply a fully compliant IBS.
Gould Named Managing Director of Kelvin Hughes
Russell Gould has been appointed managing director of Kelvin Hughes Ltd, part of the Specialty Engineering Division of Smiths Group plc. Russell joined Kelvin Hughes in 1985 as a graduate engineer responsible for the development of new navigation products. In 1995 he became head of radar techniques and was appointed engineering and operations director in 2001. For the past 5 years he has been the Company's commercial business director.
Kelvin Hughes Signs Contract
Kelvin Hughes is to supply its Nucleus3 radar and C.Plath gyrocompass to Wightlink. The St. Helen will be the first Wightlink ferry to be fitted with the Kelvin Hughes Nucleus3 5000 ATA radar system. The Nucleus3 5000 radar system, which has the ability to automatically track up to 50 targets at any one time, is ideally suited for use in high-speed craft and commercial shipping up to 10,000 tons. AIS compatible to meet future regulations
Russian Type Approval for SVDR
Kelvin Hughes Ltd. achieved Type Approval Certification from "Russian Maritime Register of Shipping" and "Ministry of Transport of the Russian Federation" for MantaDigital Simplified Voyage Data Recorder – SVDR. Interest has increased in the SVDR and the comprehensive options offered by Kelvin Hughes. Fixed installation costs and extensive replay facilities support the offering of both fixed and float-free data capsules
Kelvin Hughes Launched ETD for Radar
Kelvin Hughes has recently launched "Enhanced Target Detection" (ETD) as an enhancement to its MantaDigital range of wide-screen radars. This new facility enhances the display of slow-moving or stationary targets without interfering with the normal radar appearance or operation. ETD, the latest innovation in the MantaDigital range provided by Kelvin Hughes, treats stationary and moving returns differently, highlighting the moving ones by displaying them in a different color
SharpEye Radar Installed and Commissioned on SAS Drakensberg
Kelvin Hughes, a company in the design and supply of navigation and security surveillance systems, has announced the installation and commissioning of a SharpEye radar system on the South African Navy's fleet replenishment ship, SAS Drakensberg. In addition to X and S Band SharpEye radars the system includes IMO compliant displays and a dedicated tactical display with Kelvin Hughes Advanced Agile Tracker for helicopter approach and control.
SharpEye Radar for Trinidad & Tobago CG Patrol Craft
Kelvin Hughes, a designer and supplier of navigation and security surveillance systems, announced the installation of its new SharpEye upmast radar system on four new vessels commissioned by the Trinidad and Tobago Defence Force. The Damen Stan Patrol 5009 Coastal Patrol Vessels are all now fitted with a Kelvin Hughes Advanced Surveillance System incorporating a SharpEye X-Band radar, located upmast in a carbon composite housing with a stealth profile
Nautis Simulator Delivered to SMIT Australia
VSTEP delivers a Nautis DNV Class A FMB simulator to Seafood and Maritime Industries Training (SMIT) in Darwin, Australia for specialized ship handling, maneuvering and Radar training of coxswains. SMIT focuses on training of maritime personnel aboard fishing and recreational vessels. The company selected a Nautis DNV Class A Full Mission Bridge simulator, which allows specialized navigation and ship handling training of coxswains and maritime personnel alike in full compliance with the
Saab TransponderTech AB Receives Orders From Saab Rousemont Marine and Consilium
Saab TransponderTech has together with its partner Saab Rousemont Marine received orders from Daewoo shipyard in Korea to supply Daewoo Hull Numbers 5178 / 5179 - Oak Maritime 105K TDW Crude Oil Tankers with AIS. These are the first AIS orders for newbuildings in Korea directly placed by a shipyard, and more are to come in the near future. Also, Consilium Marine has ordered five AIS transponders for National Iranian Tanker Company to be built at Dalian New Shipyard in China
ECDIS Ltd. Unveils Vstep Nautis Bridge Simulator
ECDIS Ltd unveil Vstep Nautis Full Mission Bridge Simulator primarily for Bridge Team training but fitted with 4 ECDIS systems. UK based ECDIS training and consultancy company ECDIS Ltd unveiled the simulator at the opening of the facility by MP George Hollingbery in Southampton. The Bridge Simulator is to accompany the six smaller NAUTIS simulators already used for visual channels during the IMO 1.27 Model ECDIS Course
Ocean Signal, AMI Marine Partner
Communication and safety at sea specialist Ocean Signal and manufacturer of marine electronic equipment AMI Marine have formed a new partnership to collaborate on product development for the large commercial vessel sector. Combining the specialist knowledge and extensive technical background of
VTS Radar Systems Chosen for Port of Marseille Fos
A world leader in the design and supply of navigation and security surveillance systems, Kelvin Hughes has been contracted by French company AVON Communications to supply five of its SBS-700 radar systems for integration with the Marseille Fos Port Vessel Traffic Management System (VTMS).
SharpEye Radar for Qatari Coastguard Patrol Boats
Kelvin Hughes is to supply its SharpEye S-band radar together with its new 12kW radar for 17 patrol boats currently being built at ARES Shipyard, Turkey for Qatar's Coast and Borders Security Department. All the electronic equipment for the vessels - which include 24m, 34
Kelvin Hughes to Supply Radar for Oman Coast Guard
Kelvin Hughes has been contracted by Rodman Polyships to supply X and S band SharpEye radar systems for a range of new vessels being supplied to the Royal Oman Police Coast Guard (ROPCG). With its advanced target detection capability
Infrared Systems Protect UK Navy Ships at Sea
International manufacturer of panoramic infrared thermal imaging systems HGH Infrared Systems was selected by the British Navy to incorporate its Spynel-S 3500 into an integrated Compact Combat System (C2S) for situational awareness and ship-based protection against small fast inshore attack
Maritime Security Experts Convene in San Diego
Maritime security experts from federal, state and local jurisdictions are meeting in San Diego this week as part of Maritime Security 2015 West. Attendees from Turkey, Japan, United Arab Emirates, France, U.K., and New Zealand joined participants from across the U.S
Port of Vitória Orders Hi-res Radars
Navigation and security surveillance systems company Kelvin Hughes announced it has been contracted to supply two of its SBS-900-2 SharpEye radar systems for the Porto de Vitória in Brazil. The equipment will be provided through Spain's Indra.
TU Varna Opens Maritime Simulator Wing
New simulator wing features DNV certified VSTEP Dynamic Positioning and Full Mission Bridge Simulators and type approved ECDIS classroom. The simulation center of the Technical University of Varna officially opened its new simulation wing on May 21, 2015
Safebridge Adds Kelvin Hughes ECDIS Training
Online simulation training specialist Safebridge will launch a new training course for Kelvin Hughes MantaDigital Electronic Chart Display and Information Systems (ECDIS). Kelvin Hughes Marine Systems, a supplier of ships' bridge systems
SharpEye Radar Ordered for NZ Frigates Upgrade
As part of the Lockheed Martin Canada prime contract for the Frigate Systems Upgrade project, a contract has been awarded to Kelvin Hughes to supply SharpEye radars and with an Agile Tracker to the New Zealand (NZ) Ministry of Defense.
Safety is Job One
Maritime safety products and systems can entail everything from a sophisticated integrated bridge system down to cleaning products for the galley. Here are a few recent introductions that appear particularly topical in the never-ending push for safer ships and crews. Free Fallin'
Seagull Maritime Response on Safety, Security
Key areas of concern for seafarer safety and security in both marine and offshore operations have triggered the release of six new and one supplementary titles from computer-based training specialist Seagull Maritime. Third quarter 2014 releases include specific emphasis on the offshore
Kelvin Hughes Debuts Port Security Products
Kelvin Hughes is displaying its new combined camera and radar Single Mast Solution (SMS) at SMM 2014 in Hamburg from September 9-12. The company is also demonstrating the associated CxEye display software which provides intuitive command and control for the system.
ChartCo Debuts Improved Navigation Data Software
ChartCo, a division of Kelvin Hughes, recently announced the release of a new version of its PassageManager data management software. This latest release - PassageManager 5.1 - will be on display at SMM and incorporates a number of new features and improvements. New Features
ChartCo Acquires Regs4ships
Maritime digital data services company ChartCo acquired Regs4ships, the supplier of digital regulatory information, consultancy and training. ChartCo, part of the Kelvin Hughes Group, created a range of digital services in 1998 in anticipation of the move from paper to digital charts and


text:
We believe that advising on M&A transactions is more than providing just legal advice. Understanding the logic and dynamics of the industry sector in which the client and other participants operate is a prerequisite for success....
VJT & Partners' highly-rated employment lawyers have a wealth of experience in all aspects of contentious and non-contentious employment matters. We are acknowledged for understanding our clients' business needs and...
We are well aware that the effective management and resolution of disputes is of critical importance to companies from a corporate risk management point of view. The strategic objectives of our clients are always on our mind...
Understanding our clients' underlying technical and technological ideas and objectives, while providing clear, concise and practical advice lies at the heart of our work. The phenomenon of convergence and the rapid...
VJT & Partners can now provide its great experience to clients in the international environment of aviation because its expertise covers many aspects of aviation law from civil and commercial matters to regulatory issues.
VJT & Partners' immigration lawyers handle all aspects of business immigration cases, advising medium to high-net worth foreign individuals and multinational corporations.
We draft commercial contracts to ensure that they withstand even the most intense scrutiny from the courts in the event of a dispute. We place emphasis on both accurate and practical contractual language...
VJT & Partners advises on a wide variety of competition investigations including cartels and abuse of dominance. We often analyse and provide legal advice on exclusivity, non-compete, tying and bundling matters...
Due to the unique and rigorous requirements of the Hungarian Data Protection Act, global companies regularly face unexpected challenges in cases where technical data processors are involved, personal data is transferred outside...
Our lawyers have solid experience in a broad range of financing transactions including project, film, acquisition and property finance. We have particular strength in structuring sophisticated transactions for private equity companies...
Intellectual property is a key asset for businesses especially for clients operating in the information technology and communications sectors. Our lawyers have experience in handling IP related disputes, drafting IP related...
Restructuring, rationalising or streamlining a business: considering the potential benefits that an outsourced function can bring is always on clients' agendas. We assist our clients in realising these benefits and in minimising...
We have been at the forefront of the Hungarian private equity industry for many years. Our experience in this field has proved to be crucial to providing clients with a bespoke service from initial investment through to exit...
VJT & Partners has long-standing and successful client relationships with major market players in the most heavily regulated industries, particularly the financial services and communications sectors...
Insolvency and corporate restructuring require a comprehensive understanding of the different areas of law and the associated commercial elements. We provide integrated legal advice covering all aspects of insolvency...
Understanding our clients' underlying technical and technological ideas and objectives, while providing clear, concise and practical advice lies at the heart of our work. The phenomenon of convergence and the rapid proliferation of innovative services inspire our Information, Communications & Technology (ICT) team to continue to build unique expertise in a wide range of technology matters.
Our lawyers have particularly strong track record in commercial IT arrangements such as software licensing, call centre and hosting services as well as hardware procurement, online and e-commerce matters such as setting up web-shops. We also regularly advise on sector-specific regulatory issues concerning communications services such as licensing, interconnection and carrier-pre selection.
Our technology lawyers have been providing legal advice for a world's leading IT services provider on information technology and Business Process Outsourcing (BPO) agreements for more than a decade. We also boast one of the most experienced data protection and privacy teams in Hungary. Our transactional experience stands out as a significant number of M&A and private equity transactions handled by our corporate team require specialist technology experience.
Main Contact: János Tamás Varga
János Tamás has developed real expertise and experience across a wide range of practices, transactions and legal matters with cross-border elements over the last 18 years. His experience includes acting for both service providers and customers on a wide range of outsourcing transactions. He has advised market leading Information Technology Outsourcing (ITO) services providers on their biggest Hungarian projects in the financial services, telecommunications, energy and utility industries, and he also advises leading financial services providers as customers of BPO service providers.
+36 1 501 9900
Contact: Gábor Hacsi
Gábor leads VJT & Partners' technology practice. His experience includes drafting and negotiating technology outsourcing deals, cloud computing-based deals for both customers and suppliers in a range of industries, including IT and insurance. In the past decade he has built up a firm knowledge and experience in advising clients on data protection matters as well. In major transactions he regularly advises clients on the transfer/assignment of copyrights and other IP rights.
+36 1 501 9900
Legal 500 EMEA, 2014
The 'extremely reliable' and 'practical' team at VJT & Partners attracts particular praise for its expertise in data protection and outsourcing. 2012 saw it advise a global internet corporation on documentation relating to guest network services, and ING Insurance on data processing and marketing issues.
Chambers Europe, 2014
Premier area of expertise centred around outsourcing, with a solid client base. Handles a wide array of data protection, privacy and advertising matters, and maintains robust knowledge of IT-related regulations. Additional areas of capability include handling transactions across the sector and advising on telecoms and media issues.
Sources say: "The firm can really accommodate the business needs of the client. The lawyers are easy to work with and are always thoroughly prepared for negotiations."
"The entire team was great, very keen to understand our projects and with quick turnaround."
Managing partner János Tamás Varga is highlighted by clients for his "knowledge and understanding of the processes and policies of multinational companies," and his "insight into IT."
Legal 500 EMEA, 2013
VJT & Partners' team is 'punctual', 'business-oriented' and 'attentive to details'. It advises technology clients on data protection and online media, and has 'outstanding experience' in outsourcing. It continued to advise […] on matters ranging from data transfer to global employment. János Tamás Varga is 'an outstanding lawyer' with 'sector-specific expertise'.
Legal 500 EMEA, 2012
János Tamás Varga's 'professional' team at VJT & Partners 'focuses on the key issues'. Recent work has included large outsourcings and data protection matters as well as advice to […] on Hungary's new media legislation.
Chambers Europe, 2012
This compact local firm is a strong contender in IT and media work, and has a particularly solid reputation in data protection and online regulatory matters.
KEY INDIVIDUAL Commentators are impressed with János Tamás Varga's technical prowess and understanding of complex issues.
Legal 500 EMEA, 2011
The 'very competent' TMT team at VJT & Partners […] is 'responsive and client oriented'. János Tamás Varga leads the team and is noted for his 'good business acumen and proven industry knowledge'.
Chambers Europe, 2011
This firm acts on a diverse range of TMT matters, with particular expertise in data protection and IT. It represents […] on day-to-day data issues, commercial agreements and IT outsourcing projects. The sale of […] has been a major IT deal for the team, which also assists […] with its media interests.
KEY INDIVIDUAL János Tamás Varga 'contributes specialist knowledge and awareness of the industry,' say clients.


text:
Extent of Dental Disease in Children Has Not Decreased
GAO-08-1176T: Published: Sep 23, 2008. Publicly Released: Sep 23, 2008.
Additional Materials:
- Highlights Page:
- Full Report:
- Accessible Text:
(202) 512-7022
Office of Public Affairs
(202) 512-4800
In recent years, concerns have been raised about the adequacy of dental care for low-income children. Attention to this subject became more acute due to the widely publicized case of Deamonte Driver, a 12-year-old boy who died as a result of an untreated infected tooth that led to a fatal brain infection. Deamonte had health coverage through Medicaid, a joint federal and state program that provides health care coverage, including dental care, for millions of low-income children. Deamonte had extensive dental disease and his family was unable to find a dentist to treat him. GAO was asked to examine the extent to which children in Medicaid experience dental disease, the extent to which they receive dental care, and how these conditions have changed over time. To examine these indicators of oral health, GAO analyzed data, by insurance status, from two nationally representative surveys of the Department of Health and Human Services (HHS): the National Health and Nutrition Examination Survey (NHANES) and the Medical Expenditure Panel Survey (MEPS). This statement summarizes the resulting report being released today, Medicaid: Extent of Dental Disease in Children Has Not Decreased, and Millions Are Estimated to Have Untreated Tooth Decay (GAO-08-1121). In commenting on a draft of the report, HHS acknowledged the challenge of providing dental services to children in Medicaid, and cited the agency's related activities.
Dental disease remains a significant problem for children aged 2 through 18 in Medicaid. Nationally representative data from the 1999 through 2004 NHANES surveys--which collected information about oral health through direct examinations--indicate that about one in three children in Medicaid had untreated tooth decay, and one in nine had untreated decay in three or more teeth. Projected to 2005 enrollment levels, GAO estimates that 6.5 million children aged 2 through 18 in Medicaid had untreated tooth decay. Children in Medicaid remain at higher risk of dental disease compared to children with private health insurance; children in Medicaid were almost twice as likely to have untreated tooth decay. Receipt of dental care also remains a concern for children aged 2 through 18 in Medicaid. Nationally representative data from the 2004 through 2005 MEPS survey--which asks participants about the receipt of dental care for household members--indicate that only one in three children in Medicaid ages 2 through 18 had received dental care in the year prior to the survey. Similarly, about one in eight children reportedly never sees a dentist. More than half of children with private health insurance, by contrast, had received dental care in the prior year. Children in Medicaid also fared poorly when compared to national benchmarks, as the percentage of children in Medicaid who received any dental care--37 percent--was far below the Healthy People 2010 target of having 66 percent of low-income children under age 19 receive a preventive dental service. Survey data on Medicaid children's receipt of dental care showed some improvement; for example, use of sealants went up significantly between the 1988 through 1994 and 1999 through 2004 time periods. Rates of dental disease, however, did not decrease, although the data suggest the trends vary somewhat among different age groups. Younger children in Medicaid--those aged 2 through 5--had statistically significant higher rates of dental disease in the more recent time period as compared to earlier surveys. By contrast, data for Medicaid adolescents aged 16 through 18 show declining rates of tooth decay, although the change was not statistically significant.
Jul 7, 2016
Drug Shortages:Certain Factors Are Strongly Associated with This Persistent Public Health ChallengeGAO-16-595: Published: Jul 7, 2016. Publicly Released: Jul 7, 2016.
Jun 23, 2016
Defense Health Care:Availability and Quality Measurement of Women's Health Care Services in U.S. Military HospitalsGAO-16-596: Published: Jun 23, 2016. Publicly Released: Jun 23, 2016.
Jun 20, 2016
Federal Autism Activities:Agencies Are Encouraging Early Identification and Providing Services, and Recent Actions Could Improve CoordinationGAO-16-446: Published: May 20, 2016. Publicly Released: Jun 20, 2016.
Jun 15, 2016
Food and Drug Administration:Comprehensive Strategic Planning Needed to Enhance Coordination between Medical Product CentersGAO-16-500: Published: May 16, 2016. Publicly Released: Jun 15, 2016.
Medical Product Oversight:FDA Needs More Strategic Planning to Guide Its Scientific InitiativesGAO-16-432: Published: May 16, 2016. Publicly Released: Jun 15, 2016.
Jun 9, 2016
Medicare Fee-For-Service:Opportunities Remain to Improve Appeals ProcessGAO-16-366: Published: May 10, 2016. Publicly Released: Jun 9, 2016.
Jun 7, 2016
VA Health Care:Improvements Needed for Management and Oversight of Sole-Source Affiliate Contract DevelopmentGAO-16-721T: Published: Jun 7, 2016. Publicly Released: Jun 7, 2016.
Jun 3, 2016
VA's Health Care Budget:In Response to a Projected Funding Gap in Fiscal Year 2015, VA Has Made Efforts to Better Manage Future BudgetsGAO-16-584: Published: Jun 3, 2016. Publicly Released: Jun 3, 2016.
Jun 1, 2016
Medicare:Utilization and Expenditures for Complex Wheelchair AccessoriesGAO-16-640R: Published: Jun 1, 2016. Publicly Released: Jun 1, 2016.
May 24, 2016
Medicare Program:Continued Action Required to Address Weaknesses in Provider and Supplier Enrollment ControlsGAO-16-703T: Published: May 24, 2016. Publicly Released: May 24, 2016.
Looking for more? Browse all our products here