Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof
Reexamination Certificate
2000-10-30
2002-04-16
Killos, Paul J. (Department: 1623)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acids and salts thereof
C560S190000, C549S233000, C549S252000
Reexamination Certificate
active
06372943
ABSTRACT:
TECHNICAL FIELD
The present invention relates to novel polyenepolycarboxylic acids, or derivatives thereof at their carboxyl group(s) or their salts (which may hereinafter be referred to as “polyenepolycarboxylic acids” simply), anr d more specifically, to such polyenepolyearboxylic acids having superior dispersing ability which are produced by microorganisms belonging to genus Talaromyces.
BACKGROUND ART
Heretofore, there have been used surface active agents, macromolecular polymers and the like as dispersants for industrial purposes in a variety of fields such as pigments, coatings, cosmetic articles, coated paper, dyes, ceramics, and building and civil engineering, and particularly in recent years such compounds have been generally used in the production of fine particles.
Since these compounds thus widely used as dispersants for industrial purposes are frequently synthetic organic compounds, such compounds mostly are inferior in safety, biodegradability and like characteristics though possessing excellent dispersing ability. Therefore, depending on the manner of use, there is a fear that such compounds may raise problems such as bad influence on living bodies, environmental pollution, and scattering of such compounds in the environment.
Attention is now focused on dispersants originating from natural products which exhibit superiority in both the biodegradability and safety and hence are friendly to the terrestrial environment. Examples of such dispersants include xanthan gum, which is a polysaccharide produced by a microorganism and which is widely used in various industrial fields, taking advantage of its viscosity. However, xanthan gum has poor dispersing ability with respect to inorganic or oleaginous ingredients used in pigments, coatings and the like though offering superior safety.
Other such dispersants include saccharic acids such as sodium gluconate, which are used in a part of industry but find a limited range of application as dispersants since situations and sorts of dispersoids to which they are applicable are limited.
Accordingly, it has been earnestly desired to provide a compound originating from a natural product which is capable of exhibiting superior dispersing ability irrespective of the sort of dispersoid be used.
DISCLOSURE OF INVENTION
A compound according to the present invention having attained the above object is characterized by polyenepolycarboxylic acids represented by the following formula (1):
(wherein n represents an integer of 0 to 5 and m represents an integer of 1 or 2, provided m is 1 when n is 0), or derivatives thereof at their carboxyl group(s) or their salts. Those compounds of the above formula (1) wherein m=1 and n=0; m=2 and n=1; m=2 and n=2 are preferred embodiments of the present invention.
A dispersant according to the present invention having attained the above object is characterized by containing polyenepolycarboxylic acid(s) represented by the above formula (1) wherein n represents an integer of 0 to 5, and m represents an integer of 1 or 2, or derivatives thereof at their carboxyl group(s), or their salts. Any of those compounds of the above formula (1) wherein m=2 and n=0; m 2 and n=1; m=2 and n=2 is a preferred embodiment of the present invention.
The polyenepolycarboxylic acids represented by the above formula (1) (wherein n represents an integer of 0 to 5 and m represents an integer of 1 or 2), or acid antydrides thereof or their s alts are prepared by the use of a culture solution obtained by cultivating a microorganism belonging to genus Talaromyces in a culture medium dand hence, such a preparation method is included in the scope of the invention. Also, the microorganisms that produce the polyenepolycarboxylic acids represented by the above formula (1) (wherein n rep resents an integer of 0 to 5 and m represents an integer of 1 or 2), or derivatives thereof at its carboxyl group(s) or their salts are included in the scope of the invention.
It is to be noted that for convenience the polyenepolycarboxylic acids represented by the above formula (1) (wherein n represents an integer of 0 to 5 and m represents an integer of 1 or 2), or derivatives thereof at their carboxyl group(s) or their salts will sometimes be referred to as “the compounds of the present invention” in the following description. Further, for simplification, the polyenepolycarboxylic acid of the above formula (1) wherein m=1 and n=0 will be referred to as “R0 compound”; the polyenepolycarboxylic acid of the above formula (1) wherein m=2 and n=0 as “S0 compounds”; the polyenepolycarboxylic acid of the above formula (1) wherein m=2 and n=1 as “S1 compound”; and the polyenepolycarboxylic acid of the above formula (1) wherein m=2 and n=2 as “S2 compound”. Similarly, those R0, S0, S1 and S2 compounds in which two carboxyl groups bonded to adjacent carbon atoms are entirely bonded together to form an acid anhydride will simply be referred to as “R0 anhydride”, “S0 anhydride”, “S1 anhyd ride”, and “S2 anhydride”, respectively. The structural formulae of these compounds are shown below.
BEST MODE FOR CARRYING OUT THE INVENTION
As a result of intensive study by the inventors of the present invention, it has been discovered that compounds produced by strain No. 10092 belonging to genus Talaromyces have superior dispersing ability with respect to various dispersoids in whether aqueous or non-aqueous systems. The present invention has been made based on this discovery.
The compounds represented by the above formula (1) wherein n is an integer of 1 to 5 and m is 1 or 2, or wherein n is 0 and m is 1 are novel compounds that were discovered by the inventors of the present invention for the first time. It should be noted that the compound of the formula (1) wherein n is 0 and m is 2 is known from, for example, Aldridge, D C et al, J. C. S. Perkin I, 1980, 2134 (isol, struet, nmr), which discloses an acid anhydride of a tricarboxylic acid represented by the following formula:
and describes that this compound is obtainable from Paecilomyces variotii, a sort of fungi. Another literature reference, Jabbar, A et al., Pharmazie, 1995, 50, 706 (isol, props), describes that an analogous compound can be isolated by Penicillium sp. These literature references, however, are silent on the dispersing ability of the aforementioned compounds.
Accordingly, the compounds of the formula (1) wherein n is an integer of 0 to 5 and m is 1 or 2 are within the scope of the present invention, so long as they are used as dispersants.
In the description of the instant application, the term “lower” means the number of carbon atoms from 1 to 6.
The compounds of the present invention include, in addition to the polyenepolycarboxylic acids represented by the formula (1), derivatives thereof at its carboxyl group(s) or their salts.
Examples of “derivatives thereof at their carboxyl groups” include compounds of the formula (1) wherein the carboxyl groups thereof are, either partially or entirely, salts, anhydrides, esters, amides or the like. These derivatives also include compounds of the formula (1) wherein the carboxyl groups thereof are, either partially or entirely, in combination of them. Specifically, examples of such derivatives include compounds of the formula (1) wherein part of the carboxyl groups is an ester, while the rest is an anhydride. The above expression “their salts” means salts of the for egoing derivatives, examples of which include compounds of the formula (1) wherein part of the carboxyl groups is a derivative as above, while the rest is a salt.
The “salts” as stated above are any common non-toxic salts without any particular limitation to specific sorts thereof. Examples of such salts include alkali metal salts (such as sodium salts and potassium salts), alkali earth metal salts (such as calcium salts and magnesium salts), ammonium; salts, organic base salts (such as trimethylamine salts, triethylamine salts, pyridine salts, picoline salts,
Kakiuchi Toshihito
Kasuga Shinobu
Okada Kazuki
Yamanishi Ryo
Fujisawa Pharmaceutical Co. Ltd.
Killos Paul J.
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