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United States Patent (19) 11 4,187,251 Schleppnik 45) Feb United States Patent (19) 11 4,187,251 Schleppnik 45) Feb. 5, 1980 (54) MALODOR COUNTERACTANTS Primary Examiner-Norman Morgenstern 76 Inventor: Alfred A. Schleppnik, No. 1 Hanley 57) ABSTRACT Downs, St. Louis, Mo. 631 7 The compounds represented by the structural formula (21) Appl. No.: 908,423 (22 Filed: May 22, 1978 Related U.S. Application Data 63) Continuation-in-part of Ser. No. 771,753, Dec. 16, 1976, abandoned. 51) Int. Cl.’.............................................. C07C 49/43 52 U.S. Cl. ................. ... 260/586 R; 424/76 wherein 58) Field of Search .................................... 260/586 R A, B and C each independently represent hydrogen or lower alkyl having from 1 to 4 carbon atoms, 56) References Cited provided that the sum of the carbon atoms in A, B PUBLICATIONS and C is no more than 5, Pishnamazzade et al., "C.A.”76: 139986p (1972). R represents alkyl having from 1 to 4 carbons, Pishnamazzade et al., "C.A."74: 53119e (1971). have been found to be particularly useful in composi Heymes et al., "Ann. Chim (Paris)", 1968+ 3, pp. tions and methods for counteracting malodors. Novel 543-554. compounds are also disclosed. Cantrell, “J. Org. Chem.", 32(5), pp. 1669-1672 (1967). Groves et al. "J. Chem. Soc. C''', 1968(17), 2215-2217. 2 Claims, No Drawings 4,187,251 1 2 notorious classes of lower carboxylic acids, thiols, thio MALODOR COUNTERACTANTS phenols, phenols, lower amines, phosphines and arsines. The compounds 4-cyclohexyl-4-methyl-2-pentanone CROSS-REFERENCES TO RELATED has heretofore been found to possess the ability to coun APPLICATIONS m 5 teract such malodors. This application is a continuation-in-part of applica The following compounds have been described in the literature: tion Ser. No. 771,753, filed Dec. 16, 1976, now aban cyclohexyl methyl ketone-R. P. Mariella & R. R. doned. w Raube, JACS 74; 518 (1952) FIELD OF THE INVENTION O cyclohexyl ethyl ketone-C. Hell & O. Schaal, Ber. 42; This invention relates to the art of treatment of offen 2230 (1909) sive odors, more particularly, to compositions and cyclohexyl isopropyl ketone-E. P. Burrows, F. J. Welch & H. S. Mosher, JACS 82; 880 (1960) methods to counteract certain malodors. cyclohexyl n-propylketone-G. Darzens & H. Rost, DESCRIPTION OF THE PRIOR ART 15 Compt. rend. 153; 772 (1911) The art of perfumery began, perhaps in the ancient cyclohexyl n-butyl ketone-E. P. Burrows, F. J. Welch cave dwellings of prehistoric man. From its inception, & H. S. Mosher, JACS 82; 880 (1960) and until comparatively recently, the perfumer has uti 2-methylcyclohexyl methyl ketone-A. Heymes, M. lized natural perfume chemicals of animal and vegetable Dvolaitzky & J. Jacques, Ann. chim. (Paris) 3; 543 origin. Thus, natural perfume chemicals such as the 20 (1968) essential oils, for example, oil of rose and oil of cloves, 3-methylcyclohexyl methyl ketone-M. Mousseron, R. and animal secretions such as musk, have been manipu Granger & J. Claret, Bull, so, chim, 598 (1947) lated by the perfumer to achieve a variety of fragrances. 4-methylcyclohexyl methyl ketone-N. Duford & E. In more recent years, however, research perfume chem Flamand, Canad. J. Chem, 46, 1073 (1968) ists have developed synthetic materials having charac 25 teristics particularly desired in the art. These synthetic SUMMARY OF THE INVENTION aroma chemicals have added a new dimension to the The present invention provides compounds and com ancient art of the perfumer, since the compounds pre positions which are especially useful in view of their pared are usually of a stable chemical nature, are inex ability to counteract malodors. Furthermore, novel pensive as compared with the natural perfume chemi 30 methods are provided, i.e. the use of such compounds cals and lend themselves more easily to manipulation and compositions to counteract malodors. Still further, than the natural perfume chemicals since such natural certain of these compounds are novel. perfume chemicals are usually a complex mixture of The compounds which exhibit this surprising ability substances which defy chemical analysis. In contrast 35 to counteract malodors are represented by the follow thereto, the synthetic aroma chemicals possess a known ing structural formula: chemical structure and may therefore be manipulated by the perfumer to suit specific needs. Such needs vary A. (1) over a very wide spectrum. Accordingly, there is a great need in the art of fragrance compositions for com 40 pounds possessing specific olfactory characteristics. Heretofore a major effort in the art of perfumery has been directed to providing means of treating odors that are offensive to the human sense of smell. Such odors encompass a variety of odors such as bathroom-odor, 45 wherein kitchen-odor, body-odor, cigar smoke-odor, etc. Many A, B and C each independently represent hydrogen, a products have been developed in an attempt to over lower alkyl having from 1 to 5 carbon atoms (preferably come these odors. So-called "room fresheners" or from 1 to 4 carbons or from 1 to 3 carbons), provided "room deodorants' are illustrative of such products. that the sum of the carbon atoms in A, B and C is no In general these products have provided a masking 50 more than 7 (preferably no more than 6, especially no effect by one of two mechanisms. The maskant fra more than 5), and grance is provided either to suppress the offensive odor R represents an alkyl having from 1 to 6 carbon by providing a more pleasing aroma in large quantities atoms (preferably from 1 to 5, especially from 1 to or by providing an aroma that blends with the offensive 4). odor to provide a different and more desirable aroma. 55 In the above formula, especially preferred are those Unfortunately, in both instances a large amount of fra compounds wherein A, B and C independently repre grance must be utilized which in itself often proves to sent hydrogen, methyl, ethyl or propyl; the sum of the be offensive. Furthermore, the offensive odor is usually carbon atoms in A, B and C is no more than 5 and R1 still detectable at the levels of maskant fragrances that represents methyl, ethyl, propyl or butyl. are reasonably tolerable. Accordingly, compositions 60 and methods for counteracting such offensive odors DESCRIPTION OF THE PREFERRED which would substantially eliminate such odors without EMBODIMENTS the above-noted disadvantages are particularly desir The term "counteract' as used herein means the ef able. fect on the human sense of smell and/or the malodor Particularly noxious odors are caused by compounds 65 resulting in alleviating the offensiveness of the malodor which have a pronounced tendency to either donate or to the human sense of smell. It is not intended that this accept protons. Such compounds will hereinafter be term be limited to any particular mechanism by which referred to as "malodors." They include the olfactory such a result may be obtained. 4,187,251 3. 4. The compounds useful in this invention can prefera tions, etc., medicated hair care products containing bly be prepared as illustrated by the following equation: such ingredients as S-Selenium-sulfide, coal tar, salicy lates, etc., or shampoos, or foot care products such as foot powders, liquids or colognes, after shaves and body A A (I) 5 lotions, or soaps and synthetic detergents such as bars, B + RCC1-G B O liquids, foams or powders; in odor control such as dur 21 ing manufacturing processes, such as in the textile fin C C ishing industry and the printing industry (inks and pa Rl 10 per); in effluent control such as in processes involved in pulping, stock yard and meat processing, Sewage treat A (II) ment, or garbage disposal, or in product odor control as B in textile finished goods, rubber finished goods, car -O + H2 cat. G fresheners, etc.; in agricultural and pet care products C 15 such as dog and hen house effluents, and domestic ani Rl mal and pet care products such as deodorants, shampoo A or cleaning agents, or animal litter materials; in large B scale closed air systems such as auditoriums, and sub OH ways and transport systems. C 20 The amount of any such compound to be utilized has R been found to be independent, in general, of the particu A (III) lar malodor involved. Likewise, the concentration of the malodor in the air containing it has been found to B oxidation not effect the effective amount of the compound uti C lized. An amount effective to counteract the malodor R1 should be used. The amount of any such compound A however depends on the medium in which the com B pound is used, the temperature, humidity, air volume O 30 21 and air circulation. In general, such compounds are C effective when present in air (containing the malodor) Rl at levels as low as 0.01 mg/cubic meter of air. Of In the above equations, A, B, C and Rhave the same course, depending on the structure of the particular meanings as set forth above. 35 compound used, some compounds are more active than As shown in equation (I) a substituted or unsubsti others. Any concentration above this amount will gen tuted benzene is acylated, preferably under Friedel erally be effective. However, from a practical point of Crafts conditions, with an acyl chloride to form the view, more than about 1.0 to 2.0 mg/cubic meter of air corresponding phenyl-alkyl ketone. As shown in equa is probably unnecessary. tion (II) this phenyl-alkyl ketone is hydrogenated over a 40 Novel compounds useful in the present invention are suitable catalyst, preferably a rhodium metal-containing 4-ethylcyclohexyl methyl ketone and 4-isopropylcy catalyst, to form the corresponding alkylated cyclohex clohexyl methyl ketone.
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