Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...
Reexamination Certificate
2000-11-09
2002-11-26
Carr, Deborah D. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Fatty compounds having an acid moiety which contains the...
Reexamination Certificate
active
06486333
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to a functional alcohol releasing substance which gradually releases a functional alcohol and to a composition such as of a detergent or softening agent, which contains the functional alcohol releasing substance.
2. Description of the Related Art
In a fragrance, a desired aroma is created by blending a large number of aromatic components so-called top note, middle note and base note having different volatility. During the use of the fragrance, components having higher volatility vaporize in priority and, as a result, the aroma of the fragrance changes with the lapse of time, thus posing a problem in that the aroma cannot be maintained constantly for a prolonged period of time. A gel-like aromatic composition in which a fragrance is included in microcapsules and dispersed in a gel base material is known as a means for solving such a problem (JP-A-63-260567; the term“JP-A” as used herein means an “unexamined published Japanese patent application”). Though this method is effective in gel-like preparations, the desired effect cannot be obtained in the case of liquid preparations having low viscosity due to generation of floating and precipitation of microcapsules.
In addition to the above, a precursor of fragrance raw material in which a sugar and an amino acid are added to a fragrance raw material and a technique for gradually releasing the fragrance raw material by allowing an enzyme to act upon the precursor have been disclosed (JP-A-4-170961). This method, however, has problems in that its effect in the actual use system varies depending on the presence or absence of the hydrolyzing enzyme and, when the precursor and hydrolyzing enzyme are simultaneously blended in a product system, hydrolysis progresses in the product. It also poses the same problems in volatile antibacterial and antifungal agents, so that it is difficult to maintain their effects. In addition, even a nonvolatile substance, e.g. in the case of a water-soluble substance, cannot maintain its effect due to its washing with water.
On the other hand, WO 96/38528 discloses a betaine ester quaternary ammonium salt derivative which can gradually release a fragrance raw material alcohol. However, this betaine ester quaternary ammonium salt is apt to cause side reactions at the time of synthesis and has a considerably high hydrolyzing rate even in a neutral to weakly acidic aqueous solution, so that it has a disadvantage of poor blending stability.
SUMMARY OF THE INVENTION
An object of the invention is to provide a functional substance releasing compound which can be stably blended independent of the form and use of preparations and can gradually release a functional substance constantly for a prolonged period of time in an actual use system.
The invention is a substance which is a betaine ester of a functional alcohol, in which it has an amido bond in its molecule and releases the functional alcohol, and a composition containing the same.
The term betaine ester as used herein means a structure in which a free acid as the hydration product of betaine and an alcohol are esterificated.
DETAILED DESCRIPTION OF THE INVENTION
As the functional alcohol releasing substance of the invention, a compound represented by a general formula (I) (to be referred to as betaine ester (I) hereinafter) can be exemplified:
wherein each of R
1
, R
2
and R
3
independently represents hydrogen atom or a straight- or branched-chain alkyl or alkenyl group having from 1 to 30 carbon atoms, Y represents a straight- or branched-chain alkylene group having from 1 to 4 carbon atoms, Z is a group represented by —R
5
(OA) n— (wherein R
5
is a straight- or branched-chain alkylene group having from 1 to 30 carbon atoms, and A is a straight- or branched-chain alkylene group having from 2 to 4 carbon atoms, and n is a number of from 0 to 10), R
4
represents a residue in which one OH is removed from a functional alcohol having at least one hydroxyl group in its molecule, illustratively, R
4
represents a saturated or unsaturated aliphatic hydrocarbon group or aromatic hydrocarbon group having from 1 to 11 carbon atoms, or an alkadienyl group, alkatrienyl group, aryl group, arylalkyl group or monocyclic, bicyclic or tricyclic terpene hydrocarbon group, each having from 12 to 30 carbon atoms, wherein a part of the hydrogen atoms on the hydrocarbon group of R
4
may be substituted by a halogen atom or hydroxyl group, the methylene group in the hydrocarbon group of R
4
may be substituted by carbonyl group, amido bond, oxygen atom or sulfur atom, the methyl group may be substituted by formyl group or —CONH
2
, the carbon-carbon double bond may be substituted by epoxy group and, when isomers are present in R
4
, it may be a mixture of isomers, and X
−
represents an anion.
In this case, the alkyl group, alkenyl group and alkylene group may have a substituent group, and examples of the substituent group include an aryl group such as phenyl group, an alkoxy group such as methoxy group or ethoxy group and an aryloxy group such as phenoxy group.
The betaine ester (I) can be obtained for example by allowing a compound represented by a general formula (III) (to be referred to as compound (III) hereinafter) to react with a compound represented by a general formula (IV) (to be referred to as compound (IV) hereinafter) in the presence of a solvent:
wherein R
1
, R
2
, R
3
, R
4
, X, Y and Z are as defined in the foregoing.
Examples of the solvent to be used include diethyl ether, acetone and chloroform which are selected in response to the solubility of each material. The reaction temperature can be selected within the range of from 15 to 100° C. depending on the boiling point of the solvent used and is preferably from 25 to 50° C., more preferably from 40 to 45° C. Regarding the blending ratio of the compound (III) and compound (IV), it is desirable to use excess amount of the compound (IV) in order to increase the reaction ratio and facilitate purification of the product, and it is preferably within the range of from 1:1 to 1:1.2 by molar ratio for practical purpose.
The compound (III), when the number of carbons of the acyl group represented by R
3
CO— is 8 or more, can be quantitatively obtained by heat-melting the corresponding fatty acid at 160 to 180° C. in an atmosphere of nitrogen and slowly adding a compound represented by a general formula (V) dropwise thereto, thereby effecting dehydration condensation. Also, when the number of carbons of the acyl group represented by R
3
CO— is less than 8, it can be obtained by allowing an acid anhydride or acid chloride of the corresponding fatty acid to react with the compound of general formula (V).
In this formula, R
1
, R
2
and Z are as defined in the foregoing.
The compound (IV) can be obtained by condensing a compound represented by a general formula (VI) with an alcohol represented by a general formula (VII) in the presence of amine as a base.
In the above formulae, R
4
, X and Y are as defined in the foregoing, and B represents a halogen atom.
Among compounds of the betaine ester (I), particularly preferred is a compound represented by a general formula (II) (to be referred to as betaine ester (II) hereinafter).
In this formula, R
1
, R
2
, R
3
, R
4
, n and X
−
are as defined in the foregoing, R
6
represents hydrogen atom or methyl group, a is 1 or 2.
In the betaine ester (II), each of R
1
and R
2
is preferably a group having from 1 to 4 carbon atoms, more preferably methyl group. R
3
is preferably a group having from 1 to 22 carbon atoms. Preferably, n is from 0 to 3. Examples of the anion represented by X
−
include halogen ions, sulfate ion, hydrogensulfate ion and perchlorate ion, of which chlorine ion is preferred.
Also, the following can be cited as illustrative examples of the group represented by R
4
.
(1) Saturated or unsaturated, substituted or unsubstituted aliphatic hydrocarbon group having from 1 to 11 carbon atoms:
A reside in which one hydroxyl group is removed from an aliphatic alcohol such
Gema Takami
Hirayama Ryoichi
Katayama Atsushi
Murayama Koichi
Tanaka Shigeyoshi
Carr Deborah D.
Kao Corporation
Oblon & Spivak, McClelland, Maier & Neustadt P.C.
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