Cleaning compositions for solid surfaces – auxiliary compositions – With oxygen – halogen – sulfur – or nitrogen containing or... – Ring in the component
Reexamination Certificate
2000-11-28
2002-12-03
Hardee, John (Department: 1751)
Cleaning compositions for solid surfaces, auxiliary compositions
With oxygen, halogen, sulfur, or nitrogen containing or...
Ring in the component
C512S022000, C560S231000
Reexamination Certificate
active
06489273
ABSTRACT:
BACKGROUND TO THE INVENTION
The present invention relates to a fragrance having a 2-cyclohexyl-1,1-dimethyl ethanol derivative represented by formula (1)
wherein R represents a hydrogen or an acetyl group, Me represents a methyl group, and n represents an integer from 0 to 3.
In addition, the present invention relates to a fragrance composition containing as an active component a fragrance comprising one or two or more types of 2-cyclohexyl-1,1-dimethyl ethanol derivative represented by the above formula (1). The present invention also relates to an aromatic bleaching composition containing this fragrance composition.
In recent years, with the increasing variety in various perfume products and sanitation products, there are a variety of expectations for fragrances useful for adding scents to these products. Fragrances that provide a pleasant scent, or fragrances that have a very distinctive and agreeable scent, have been sought. Furthermore, there has been increasing demand for fragrances that match the characteristics of individual products. At the same time, in terms of the properties of the fragrance itself, there is a need for fragrances that are chemically stable, while mixing well with other fragrances.
To satisfy these demands, it has always been very important for the fragrance industry to develop and provide fragrance materials that have both individual distinctive characteristics as well as an agreeably pleasing scent.
U.S. Pat. No. 4,006,218 discloses a 2-cyclohexyl-1,1-dimethyl ethanol compound. This compound is used together with an anti-microbial agent, such as cetyl pyridinium chloride, which is commonly used in anti-microbial compositions to increase the anti-microbial action. In addition, Japanese Laid-Open Patent Publication Number 2-31683 discloses 2-cyclohexyl-1,1-dimethyl ethanol as an active component of a pest repellent.
As disclosed in Japanese Examined Patent Publication Number 7-65067, the scent characteristic of 4-cyclohexyl-2-methyl-2-butanol is effective in developing a floral fragrance that is reminiscent of lily of the valley. Methods are disclosed for providing, improving, or modifying the floral fragrance by mixing the compound with other fragrances. Furthermore, Japanese Laid-Open Patent Publication Number 7-238297 discloses 2-cyclohexyl-2-propylesters as fragrance compounds.
However, there are no descriptions of the scent characteristics of 2-cyclohexyl-1,1-dimethylethanol compounds and their acetates and the like. In addition, there are no descriptions of methods for using these compounds as fragrance materials used in adding scent to various perfume products and sanitation materials.
OBJECTS AND SUMMARY OF THE INVENTION
It is an object of the present invention to provide a fragrance material that overcomes the foregoing problems.
It is a further object of the present invention to provide a fragrance material that is very pleasing and satisfies the requirements corresponding to the product characteristics, that has excellent stability in the product, and that can be mixed well with other fragrances.
It is still a further object of the present invention to provide a fragrance composition comprising this fragrance material as an active component.
It is another object of the present invention to provide a method for using this fragrance composition.
As a result of intensive research to attain the above objectives, the present inventors have discovered that 2-cyclohexyl-1,1-dimethyl ethanol derivatives have a pleasing and highly unique scent, are chemically stable, and have excellent harmony with other fragrances. The present invention includes each of the following embodiments:
(1) A fragrance comprising a 2-cyclohexyl-1,1-dimethyl ethanol derivative represented by formula (1)
wherein R represents a hydrogen atom or an acetyl group, Me represents a methyl group, and n represents an integer from 0 to 3;
(2) A fragrance composition comprising, as an active component, a fragrance material comprising one or more types of 2-cyclohexyl-1,1-dimethyl ethanol derivatives as described in the above item (1);
(3) An aromatic bleaching composition comprising a fragrance composition described in the above item (2).
The above, and other objects, features, and advantages of the present invention will become apparent from the following description read in conjunction with the accompanying drawings, in which like reference numerals designate the same elements.
DETAILED DESCRIPTION OF THE INVENTION
Each of the following compounds are concrete examples of the 2-cyclohexyl-1,1-dimethyl ethanol derivative represented by formula (1) in each of the above described embodiments:
2-cyclohexyl-1,1-dimethyl ethanol;
2-cyclohexyl-1,1-dimethyl ethyl acetate;
2-(2-methylcyclohexyl)-1,1-dimethyl ethanol;
2-(2-methylcyclohexyl)-1,1-dimethyl ethyl acetate;
2-(3-methylcyclohexyl)-1,1-dimethyl ethanol;
2-(3-methycyclohexyl)-1,1-dimethyl ethyl acetate;
2-(4-methylcyclohexyl)-1,1-dimethyl ethanol;
2-(4-methylcyclohexyl)-1,1-dimethyl ethyl acetate;
2-(2,3-dimethylcyclohexyl)-1,1-dimethyl ethanol;
2-(2,3-dimethylcyclohexyl)-1,1-dimethyl ethyl acetate;
2-(2,4-dimethylcyclohexyl)-1,1-dimethyl ethanol;
2-(2,4-dimethylcyclohexyl)-1,1-dimethyl ethyl acetate;
2-(2,5-dimethylcyclohexyl)-1,1-dimethyl ethanol;
2-(2,5-dimethylcyclohexyl)-1,1-dimethyl ethyl acetate;
2-(2,4,6-trimethylcyclohexyl)-1,1-dimethyl ethanol; and
2-(2,4,6-trimethylcyclohexyl)-1,1-dimethyl ethyl acetate.
Among the compounds given as examples above, as well as others generically embodied in the present invention, there may be a plurality of isomers, including stereoisomers and optical isomers, based upon the methyl group substitution(s) on the cyclohexane ring. Any of these isomers, or a mixture of several of these isomers are useful in the present invention.
The above described 2-cyclohexyl-1,1-dimethyl ethanol derivatives all have a distinctive green floral scent. It has been observed that alcohols have a fresher scent nuance, and acetates have more of a rose scent nuance.
The 2-cyclohexyl-1,1-dimethyl ethanol derivatives of the present invention can be manufactured by, for example, the Grignard reaction described in Shinjikken Kagaku Kouza (published by Maruzen Corp. Ltd.), volume 14: pages 512-514, acetylation reaction described in the same, volume 14: pages 1014-1016, and hydrogenation reaction described in the same, volume 15: pages 426-428, each of which is herein incorporated by reference. Stated more concretely, the 2-cyclohexyl-1,1-dimethyl ethanol derivatives of the present invention can be manufactured by following the following reaction steps.
wherein Me represents a methyl group, Ac represents an acetyl group, X represents a halogen, and n is an integer from 0 to 3.
In the manufacture method for the 2-cyclohexyl-1,1-dimethyl ethanol derivative of the present invention according to the above reactions, first, a Grignard reagent, that is prepared, in an ether solvent such as tetrahydrofuran, diethyl ether, or the like, from magnesium metal and the starting substance of a halogenated benzyl, represented by general formula (2), is reacted with acetone. Normally, the reaction temperature is at −10~50° C., and preferably at 0~30° C. As a result, a benzyl alcohol represented by the general formula (3) is obtained.
Next, by reducing the resulting benzyl alcohol (3) using hydrogen gas in the presence of a hydrogenation catalyst, an alcohol compound of the present invention represented by general formula (4) is obtained. This reaction can proceed without a solvent, but alcohol solvents such as ethanol or methanol and the like, hydrocarbon solvents such as hexane or heptane and the like, ester solvents such as ethyl acetate or butyl acetate and the like can be selected and used as appropriate. Examples of hydrogenation catalysts used in this reaction include Raney® nickel, ruthenium/silica, ruthenium/alumina, rhodium/silica, rhodium/alumina, palladium/carbon, and the like. The normal reaction temperature is 0~200° C., preferably 50~150° C. The normal hydrogen pressure is about 1×10
6
pa~2×10
7
pa
Aida Takashi
Matsuda Hiroyuki
Yamasaki Tetsuro
Darby & Darby
Hardee John
Takasago International Corporation
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