Cleaning compositions for solid surfaces – auxiliary compositions – Cleaning compositions or processes of preparing – Specific organic component
Reexamination Certificate
2001-09-24
2003-05-27
Raymond, Richard L. (Department: 1624)
Cleaning compositions for solid surfaces, auxiliary compositions
Cleaning compositions or processes of preparing
Specific organic component
C514S563000, C562S571000
Reexamination Certificate
active
06569829
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a long chain N-acyl acidic amino acid or a salt thereof, and a simple process for producing the same. More specifically, the present invention relates to a long chain N-acyl acidic amino acid or a salt thereof, which has substantially no odor and can be applied even to non-perfume fields, which is diminished in a content of water soluble impurities such as inorganic salts and reaction by-products of free fatty acid, and which is suitable for the production of a detergent or a cosmetic composition, wherein the detergent prepared by incorporating it into a liquid detergent causes neither precipitation nor turbidity.
BACKGROUND ART
An amine or alkali metal salt of a long chain N-acyl acidic amino acid has been extensively used as a surface active agent and an antibacterial agent owing to its surface activity. Particularly, it is extensively used in detergents and cosmetic fields such as quasi-drugs and cosmetics, and in many cases comes in direct touch with the human body. Therefore, it is prohibitive to give users an unpleasant feeling. In such fields, it is frequently required that final products produce no turbidity, and the odor of the final products has an important value to the commodity. Therefore, in using the long chain N-acyl acidic amino acid or a salt thereof in such fields, it is desired to diminish impurities capable of causing turbidity of the final products and those capable of unfavorably affecting the odor of the final products to the utmost.
U.S. Pat. No. 3,758,525 discloses a process for producing a long chain N-acyl acidic amino acid, wherein an acidic amino acid and a long chain fatty acid halide are subjected to condensation reaction in the presence of an alkali using a mixed solvent of 15 to 80% by volume of a hydrophilic organic solvent and 85 to 20% by volume of water, and after the reaction is over, the reaction liquid is adjusted to pH 1, thereby precipitating a crude crystal of a long chain N-acyl acidic amino acid, which is separated by filtration and washed to remove the hydrophilic organic solvent, whereby a desired long chain N-acyl acidic amino acid is obtained. However, the long chain N-acyl acidic amino acid obtained according to said process contains inorganic salts because of insufficient removal thereof, and moreover, the process for separating the long chain N-acyl acidic amino acid as mentioned above is not industrially advantageous from a viewpoint of equipment and operation.
JP-A 51-13717 discloses a process, wherein a reaction liquid obtained by the reaction between an acidic amino acid and a long chain fatty acid halide in a mixed solvent of water and a hydrophilic organic solvent in the presence of an alkali, is adjusted to pH 1 to 6 using a mineral acid at a temperature of from 40° C. to a boiling point of said hydrophilic organic solvent, thereby separating into an aqueous layer and an organic layer containing a desired product, and the hydrophilic solvent is then removed from the organic layer to obtain a long chain N-acyl acidic amino acid. However, according to the process, a content of inorganic salts decreases only to a degree of 1 to 2%, and odoriferous substances originating in the solvent are insufficiently removed. In Examples thereof, it is specifically disclosed that most of the acetone is removed from the organic layer by means of vacuum-heating, and then the remaining acetone is removed in a manner such that water is added to the residue and air is blown to its liquid surface while stirring the liquid at 65° C. However, according to such a solvent removing method as blowing of air to the liquid surface, it is difficult to completely remove the remaining acetone or remove high boiling odoriferous substances mentioned below.
Further, in JP-A 3-284685 of the same applicant as that of U.S. Pat. No. 3,758,525 and JP-A 51-13717, acetone and its aldol-condensation products such as diacetone alcohol and mesityl oxide are named as substances, which remain in the long chain N-acyl acidic amino acid, and which causes an odor in the goods. And it is also disclosed therein that even when the process disclosed in JP-A 51-13717 is used, these odoriferous substances cannot be removed completely and as a result, these are left in the long chain N-acyl acidic amino acid and cause an odor of the products. On such a premise, it is further disclosed to remove these odoriferous substances and salts from an aqueous solution of a salt of the long chain N-acyl acidic amino acid by means of reverse osmosis membrane. However, the process is disadvantageous from a viewpoint of using an expensive membrane separation apparatus, and it cannot be said that the process is simple from an industrial point of view, because the process cannot be carried out without complicated operation control such as control of concentrations and control of membranes.
JP-A 50-5305 discloses that in subjecting an amino acid and a long chain fatty acid halide to condensation in the presence of an alkali, an aqueous lower alcohol is used as a reaction solvent, and as the aqueous lower alcohol, methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol and sec-butanol are specifically enumerated in a limited manner. However, all the above-mentioned alcohol are primary or secondary, and therefore in a step of making a pH of the liquid acidic, a dehydration-condensation reaction occurs between the formed long chain N-acyl acidic amino acid and said alcohol solvent, thereby resulting in the production of an ester. In addition, a dehydration-condensation reaction occurs also between said alcohol solvent and a free fatty acid by product through hydrolysis of the raw material of long chain fatty acid halide, thereby producing an ester. The thus produced ester is a compound which is difficult to separate and remove from the long chain N-acyl acidic amino acid.
JP-A 7-2747 also proposes a separation process using a membrane, which is, however, disadvantageous like in the process disclosed in JP-A 3-284685. In Comparative Example of JP-A 7-2747, it is disclosed to directly condense the obtained long chain N-acyl acidic amino acid-containing organic layer, and it is demonstrated that a free fatty acid remarkably increases in the course of said condensing, and the hydrophilic organic solvent is hardly removed.
JP-A 3-279354 discloses a reaction process wherein a mixed solvent of water and an hydrophilic organic solvent consisting of acetone and isopropanol is used to prevent the production of odoriferous components such as diacetone alcohol and mesityl oxide, which are greatly produced when acetone is used singly as the solvent. There is also disclosed a separation process wherein the acidified reaction liquid is subjected to crystallization separation to obtain crystals, which are then dissolved in a hydrophilic organic solvent, and an aqueous solution of a high concentration of sodium sulfate is added thereto, thereby separating into an organic layer and an aqueous layer. However, according to the process, there are left problems such that a step of re-dissolving the crystals once separated by crystallization is troublesome, it is inevitable for the goods to be contaminated with sodium sulfate as far as a large amount of sodium sulfate is used, and it is inevitable to treat a waste liquid containing a high concentration of sodium sulfate. Moreover, even when the mixed solvent of acetone and isopropanol is used as the hydrophilic organic solvent, it is not always sufficient to diminish diacetone and mesityl oxide to a degree such that any additional removal is not required, and as a result, it is still essential to remove these odoriferous components. In addition, with respect to removal of the organic solvent from the organic layer, an Example of said JP-A describes nothing but removal thereof by means of vacuum-heating as a specific removal means, and only describes a content of the acetone-condensation product in the long chain N-acyl acidic amino acid is a trace. It is not clear whether or not it is removed to a degree such
Tamura Yoshinaga
Yamamoto Shin-ichi
Yamawaki Yukio
Asahi Kasei Kabushiki Kaisha
Birch & Stewart Kolasch & Birch, LLP
Raymond Richard L.
Tucker Zachary C.
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