Bleaching and dyeing; fluid treatment and chemical modification – Bleaching – Chemical
Reexamination Certificate
2001-03-26
2003-11-11
Gupta, Yogendra N. (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Bleaching
Chemical
C008S108100, C008S111000, C252S186100
Reexamination Certificate
active
06645254
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to an aromatic bleaching agent composition and more particularly to an aromatic bleaching agent composition comprising a 1-substituted-2,2,4-trimethylpentane-3-one derivative.
BACKGROUND OF THE INVENTION
In recent years, with the diversification and spread of hygienic materials, etc. and the appearance of new killer colon bacilli, including coliform bacillus O-157, the term “anti-bacterial” or “disinfectant” has spread even among general consumers. Under these circumstances, today, the presence of chlorine-based bleaching agents having bactericidal action is indispensable to extermination of bacteria, vicious microorganism, fungi and acari present close to human beings.
In order to meet the consumers' need for bleaching agent which can be used not only to remove stain such as spot, yellowing and darkening from daily clothing for the purpose of meeting their liking for cleanliness as in the foregoing circumstances as well as for colored or figured clothing, an oxygen-based bleaching agent appeared on the market. Today, it is also true that the main role of the oxygen-based bleaching agent is to allow the color of the clothing to look sharp or prevent the clothing from yellowing or darkening during daily washing in addition to the conventional concept of bleaching or germicidal action. This oxygen-based bleaching agent is blended with proper surface active agents or bleaching activators to provide various washing detergents or household detergents which are widely used.
These bleaching agents can be used for many purposes as mentioned above but are disadvantageous in that they give out an offensive stimulating odor during use. For example, an aqueous solution of sodium hypochlorite, which is a typical chlorine-based bleaching agent, gives out a peculiar offensive stimulating odor. A bleaching agent containing potassium percarbonate or potassium perborate, which is an oxygen-based bleaching agent, gives out a stink characteristic to various bases incorporated therein. In order to overcome these defects in compliance with the wishes of the consumers, studies have so far been made of masking agent and perfume for aromatizing these bleaching agents.
The perfume and masking agent to be used for these purposes are subjected to restriction of chemical structure so that they stay in a stable condition in the bleaching agent components and undergo no reaction with the bleaching agent components to prevent themselves from deteriorating the effect of the bleaching agent components and from being decomposed by the bleaching agent components and hence showing deterioration or modification that lowers the commercial value thereof. For examples, those having an ether structure free of unsaturated bond (see JP-B-3-43320 (The term “JP-B” as used herein means an “examined Japanese patent publication”)), those having specific alcohol and ester structures (see JP-B-3-29280 and JP-A-2-166200 (The term “JP-A” as used herein means an “unexamined published Japanese patent application”)), etc. are known for their effectiveness. Chemical structures which are subject to chemical change under some alkaline conditions of base or upon the oxidative effect of bleaching agent, i.e., unsaturated bond, alcohols, aldehydes and ketones have been normally considered inappropriate.
On the other hand, among ketones, 1-phenyl-2,2,4-trimethyl-3 pentanone is known as a 1-substituted-2,2,4-trimethylpentane-3-one derivative which can be blended as a perfume component to provide a metallic and green rosy fragrance (see JP-A-63-203609). Further, as a compound having a geranium-like, rosy and spicy rosinol-like fragrance there is known 1-cyclohexyl-2,2,4-trimethyl-3-pentanone (see JP-A-63-203643) It is described that these compounds can be used to aromatize quality mixed perfume, perfume, soap, shampoo, hair rinse, detergent, cosmetics, hair spray, aromatic, etc.
However, the above cited patents have neither reference to the chemical stability of these compounds nor suggestions to the fact that these ketones exhibit a high stability particularly to bleaching agent against the conventional recognition. More specifically, there are no suggestions to the fact that 1-substituted-2,2,4-trimethylpentane-3-one derivatives are unprecedentedly extremely rare ketones which stay in a chemically stable condition in both a chlorine-based bleaching agent and an oxygen-based bleaching agent without deteriorating the bleaching activity thereof and thus show no deterioration of fragrance and a high masking effect. Further, there are no suggestions to the fact that an aromatic bleaching agent composition containing 1-substituted-2,2,4-trimethylpentane-3-one derivative has a remarkably high commercial value.
SUMMARY OF THE INVENTION
As previously mentioned, the recent trend is that bleaching agent components are incorporated not only in specific bleaching agents but also in daily washing detergents, etc. Accordingly, there is a growing demand for the development of a chemically stable masking agent which can be used for these purposes without deteriorating the bleaching agent components or bases. Therefore, the development of such a masking agent is very useful particularly for the art of hygienic materials, detergents, etc.
It is therefore an object of the present invention to provide a chemically stable bleaching agent composition which can exert an excellent masking effect without deteriorating the bleaching agent base.
The inventors made extensive studies of a compound which exhibits an extremely high stability even in a bleaching agent having a strong oxidative effect. As a result, it was found that a 1-substituted-2,2,4-trimethylpentane-3-one derivative is extremely stable in such a bleaching agent and has a high masking effect and an aromatic bleaching agent composition comprising such a derivative incorporated therein has a remarkably high commercial value. The present invention has thus been worked out.
The present invention provides an aromatic bleaching agent composition comprising one or more 1-substituted-2,2,4-trimethylpentane-3-one derivatives represented by the following general formula (1):
wherein X represents a benzene ring or a cyclohexane ring; and R represents an arbitrary hydrogen atom on said ring or a methyl group which substitutes said hydrogen atom.
DETAILED DESCRIPTION OF THE INVENTION
It is known that ketones normally exhibit a high reactivity and thus undergo a polymerization reaction such as aldol reaction in the presence of an alkali. It is also known that when acted upon by a peracid, ketones undergo nucleophilic reaction that leads to Baeyer-Villiger oxidation resulting in the production of esters (
Synthesis
, pp. 1324-1347, 1995). However, the 1-substituted-2,2,4-trimethylpentane-3-one derivative to be used in the invention is present in an extremely stable condition even against the alkalinity of an aqueous solution of sodium hypochlorite or upon the oxidation by sodium hypochlorite or alkaline metal salt of percarbonic acid or perboric acid because of its structurally specific and high steric hindrance. The 1-substituted-2,2,4-trimethylpentane-3-one derivative doesn't modify or deactivate these bleaching agent components and thus exerts an excellent effect of masking the odor of the bleaching agent base. It can be thus said that an aromatic bleaching agent composition having such a 1-substituted-2,2,4-trimethylpentane-3-one derivative is very useful.
The synthesis of the 1-substituted-2,2,4-trimethylpentane-3-one derivative to be used in the invention can be accomplished by a process which comprises allowing a base such as hydroxide of alkaline metal (e.g., sodium hydroxide) or hydride of alkaline metal (e.g., hydrogenated sodium) to act on diisopropyl ketone, and then adding benzyl chloride to the material, as described in JP-A-63-203609 if R and X in the general formula (1) are hydrogen atom and benzene ring, respectively.
Alternatively, if R is a hydrogen atom and X is a cyclohexane ring, the synthesis of the 1-substituted-2,2,4-trimethylp
Aida Takashi
Hagiwara Toshimitsu
Matsuda Hiroyuki
Yoneyama Tsunehide
Gupta Yogendra N.
Hamlin D G
Sughrue & Mion, PLLC
Takasago International Corporation
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