Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From carboxylic acid or derivative thereof
Reexamination Certificate
1999-08-11
2001-09-18
Nutter, Nathan M. (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From carboxylic acid or derivative thereof
Reexamination Certificate
active
06291634
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to novel polyamino acid derivatives. More specifically, the present invention relates to novel polyamino acid derivatives which are useful as a chelating agent for metallic ions such as Ca, Mg, Fe or Cu. The present invention further relates to the use of polyamino acid derivatives, inclusive of such novel polyamino acid derivatives, as 1) a pigment dispersant for paints or inks, 2) a surface-treating agent for a powder used in paints, inks, resin composite materials or toiletries, 3) a humectant in toiletries, or 4) a rust-proofing agent.
2. Discussion of the Background Art
Polyamino acid derivatives obtained by condensing amino acids or derivatives thereof through heat polymerization in such that the amino acids or derivatives thereof are bound through the peptide linkage, have been so far known. For example, polyaspartates have been used as a humectant in toiletries.
An amino acid itself contains both a carboxyl group and an amino group in the molecule, having ampholytic properties. However, since amino acids are bound, as just described, through the peptide linkage in a polyamino acid known so far, properties inherent in amino acids, for example, ampholytic properties, have been lost.
Meanwhile, it is disclosed in JP-A-9-194448 that amino acid derivatives (diamine-type polyamino acids) in which two molecules of an amino acid are bound to one molecule of a dihaloalkane or epichlorohydrin are useful as a highly biodegradable chelating agent. Further, it is disclosed in U.S. Pat. No. 3,989,636 that a copolymer of glycine or aspartic acid and epichlorohydrin (degree of polymerization n=2 to 3) has a chelating activity.
Thus, those compounds in which two or three amino acid molecules are bound through other than the peptide linkage are indeed known, but no higher-molecular compounds have actually produced and examined upon the properties thereof. And, none of the polyamino acid derivatives already known have been applied as any agents other than the chelating agent.
SUMMARY OF THE INVENTION
Under these circumstances of the background art, it is an object of the present invention to provide novel polyamino acid derivatives that can find a wide variety of uses. It is another object of the present invention to provide the novel uses of known polyamino acids.
In view of the above, the present inventors have assiduously conducted investigations, and have consequently found that a novel polyamino acid derivative characterized in that at least four amino acid molecules are bound by crosslinking groups through the nitrogen atoms of the amino groups, is excellent in dispersing activity when it is used as a pigment dispersant for paints, inks or the like, excellent in dispersing activity and providing a good touch when it is used as a surface-treating agent for a powder, excellent in chelating force when it is used as a chelating agent for metallic ions, excellent in providing a moistness to the hair or the skin when it is used in toiletries, and excellent in rust-proofing force for a metal, and that a polyamino acid derivative which has the same chemical structure as the above-mentioned novel amino acid derivative except that the number of amino acids is less than 4 and of which the use has been unknown other than as a chelating agent, is also useful as a pigment dispersant, a surface-treating agent, a toiletry ingredient or a rust-proofing agent. Such findings have led to the completion of the invention.
Accordingly, the present invention relates to novel polyamino acid derivatives characterized in that at least four amino acid molecules are bound by crosslinking groups through the nitrogen atoms of the amino groups, and to the novel uses of polyamino acid derivatives including the novel polyamino acid derivatives.
DETAILED DESCRIPTION OF THE INVENTION
The invention will be described in detail below.
First, the novel polyamino acid derivatives per se of the present invention will be described.
The novel polyamino acid derivatives of the present invention are, as has been described above, polyamino acid derivatives in which at least four amino acid molecules are bound by crosslinking groups through the nitrogen atoms of the amino groups.
As such polyamino acid derivatives, for example, those polyamino acid derivatives in which the crosslinking groups are alkylene groups which may have a hydroxyl group on, and/or an ether linkage in, the carbon chain, can be mentioned. Among such alkylene groups, a simple alkylene group is represented by Formula (1) below. An alkylene group having a hydroxyl group on the carbon chain is represented by, for example, Formula (2) below. And, an alkylene group having an ether linkage in the carbon chain is represented by, for example, Formula (3) below. According to the present invention, an alkylene group having an ether linkage in the carbon chain refers to an alkylene group of the structure in which some of the carbon atoms in the carbon chain of the alkylene group is or are replaced with oxygen atom(s).
wherein k in Formula (1) is an integer of from 1 to 10, and A in Formula (3) is, e.g., a group represented by any one of Formulas (4) to (6) below.
wherein j in Formula (4) is an integer of from 1 to 10, and m in Formula (6) is an integer of from 1 to 15.
Next, it will be described how to produce the novel polyamino acid derivatives of the present invention.
The novel polyamino acid derivatives of the present invention can be obtained, for example, by reacting epichlorohydrin and/or a polyepoxy compound or a dihaloalkane with an amino acid.
The polyepoxy compound used in the synthetic reaction of a novel polyamino acid of the present invention can be a compound having two or more oxirane groups. Specific examples of the epoxy compound include aliphatic polyepoxy compounds such as ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, glycerin triglycidyl ether, glycerin diglycidyl ether, sorbitol polyglycidyl ether, pentaerythritol polyglycidyl ether, diglycerin polyglycidyl ether and hexanediol diglycidyl ether; and aromatic polyepoxy compounds such as hydroquinone diglycidyl ether, bisphenol A diglycidyl ether and epoxy novolak. These can be used either singly or in combination of two or more thereof. Further, the polyepoxy compound can be a commercial product. It can also be formed by heating a polyol compound having two or more hydroxyl groups and epichlorohydrin in the presence of a basic catalyst such as sodium hydroxide.
Examples of the amino acid to be used in the synthsis of the novel polyamino acid derivatives of the present invention include acidic amino acids such as glutamic acid and aspartic acid; basic amino acids such as lysine, arginine and ornithine; and neutral amino acids such as glycine, alanine, &bgr;-alanine, &ggr;-aminobutyric acid, valine, leucine, isoleucine, serine, threonine, phenylglycine, phenylalanine and tryptophan. These amino acids can be used either singly or in combination of two or more thereof.
When a basic amino acid is used in producing a novel polyamino acid derivative of the present invention, a polyamino acid derivative of a higher molecular weight can more easily be obtained because a basic amino acid has a larger number of free amino groups per a molecule. When an acidic or neutral amino acid is used in producing a novel polyamino acid derivative, a novel polyamino acid derivative of a higher molecular weight can be obtained, when it is used in combination with a basic amino acid.
The amino acid to be used for the synthesis of the novel polyamino acid derivatives of the present invention can be an L-isomer, a D-isomer or a racemic modification. Among them, a racemic modification or an L-isomer is preferable because it can easily be obtained industrially,and of the two, an L-isomer is more preferable in view of the biodegradability of the product.
The reaction of epichlorohydrin and/or a polyepoxy compound with an amino acid (synthetic reaction of the novel polyamino
Tabohashi Tatsuru
Tanaka Hiroyuki
Ajinomoto Co. Inc.
Nutter Nathan M.
Oblon & Spivak, McClelland, Maier & Neustadt P.C.
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