Chemistry: natural resins or derivatives; peptides or proteins; – Proteins – i.e. – more than 100 amino acid residues – Scleroproteins – e.g. – fibroin – elastin – silk – etc.
Reexamination Certificate
1999-11-01
2001-06-05
Low, Christopher S. F. (Department: 1653)
Chemistry: natural resins or derivatives; peptides or proteins;
Proteins, i.e., more than 100 amino acid residues
Scleroproteins, e.g., fibroin, elastin, silk, etc.
C424S402000, C424S443000, C424S484000, C424S486000, C424S499000, C435S005000, C435S007920, C435S174000, C435S180000, C435S181000, C435S091500, C435S091500, C514S010100, C514S011400, C516S099000, C530S311000, C530S314000, C530S317000
Reexamination Certificate
active
06242573
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates a method of producing water-insolubilized regenerated collagen fiber, and more particularly, to a method of producing water-insolubilized regenerated collagen fiber, which can substantially maintain the color and the high knot tenacity inherent in the collagen and which also maintains chemically modifiable carboxyl groups of the collagen as it is without being chemically modified.
Among the protein fibers, the regenerated collagen fiber exhibits a high mechanical strength like silk, and, thus, is used in various fields. Particularly, the regenerated collagen fiber is a protein fiber maintaining a characteristic molecular structure derived from collagen and, thus, is close in drape, luster and feel to the human hair that is a natural protein fiber having complex fine structure. Such being the situation, it is attempted to use the regenerated collagen fiber as an animal hair-like fiber such as a fur, or the hair.
In general, the skin or bone of an animal is used as a raw material of the regenerated collagen. The regenerated collagen can be produced by treating these raw materials with an alkali or an enzyme to obtain a water-soluble collagen, followed by extruding and spinning the water-soluble collagen in an aqueous solution of an inorganic salt. Since the regenerated collagen fiber thus obtained is soluble in water, some treatments are applied in order to impart resistance to water to the collagen fiber. As a method for making the regenerated collagen fiber insoluble in water, it is known to the art to treat the water-soluble collagen fiber with an aldehyde compound such as formaldehyde or glutaric aldehyde. It is also known to treat the regenerated collagen fiber with metal salts such as various chromium salts, aluminium salts or zirconium salts to make the regenerated collagen fiber insoluble in water. In the case of using an aldehyde compound other than formaldehyde or a chromium salt, the resultant fiber is colored, resulting in limitation in the use of the treated collagen fiber for manufacturing hairs of various colors such as a white hair or a golden hair. In the case of using formaldehyde, it is certainly possible to obtain a colorless fiber. However, the treated fiber is not satisfactory in beauty.
A colorless treating method of a regenerated collagen fiber using an epoxy compound is proposed in Japanese Patent Disclosure (Kokai) No. 4-352804. In the case of using glycidyl ether of polyhydric alcohol that is described in this prior art as a particularly desirable compound, it is certainly possible to achieve a colorless treatment. However, the knot tenacity is lowered, with the result that a problem tends to be generated during manufacture of the hair decorative article such as the filling step or a sewing step included in the manufacturing process. Also, a colorless treatment can be achieved by some of the methods using the metal salts noted above. However, since the carboxyl groups, the reactive groups, in the collagen are sequestered by the metal salt, the carboxyl groups fail to be chemically modified further. As a result, it is impossible to impart a new function such as a permanent wave to the regenerated collagen fiber after the treatment.
BRIEF SUMMARY OF THE INVENTION
Accordingly, an object of the present invention is to provide a method of producing water-insolubilized regenerated collagen fiber, which can substantially maintain the color and the high knot tenacity inherent in the collagen and which also maintains chemically modifiable carboxyl groups of the collagen substantially intact without being modified.
As a result of an extensive research conducted in an attempt to achieve the above-noted object, the present inventors have found that it is possible to produce a water-insolubilized regenerated collagen fiber that can substantially maintain the color and the high knot tenacity inherent in the collagen by treating the regenerated collagen fiber with a monofunctional epoxy compound (an epoxy compound having only one epoxy group), arriving at the present invention. Particularly, in the case of using epihalohydrin as a monofunctional epoxy compound, it is possible to produce a water-insolubilized regenerated collagen fiber which can achieve permanent wave set by treating the regenerated collagen fiber with this epihalohydrin and a sulfur compound. Incidentally, the permanent wave treatment denotes a treatment to impart a desired shape, which can be maintained, to the hair by an oxidation-reduction reaction using chemicals, in a beauty saloon, at home, etc.
In the treatment of the regenerated collagen fiber with a monofunctional epoxy compound according to the present invention, the carboxyl groups of the collagen are not modified so as to be retained as they are, and thus various characteristics can be imparted to the thus treated regenerated collagen fiber by chemically modifying the carboxylic groups. In this case, a water-insolubilized collagen fiber exhibiting a color substantially equal to the original color of the collagen, that can be permanent-wave set, can be obtained by using a diamine compound having a disulfide linkage as a chemical modifying agent.
Accordingly, the present invention provides a method of producing water-insolubilized regenerated collagen fiber, which comprises treating a regenerated collagen fiber with a water insolubulizing agent comprising a monofunctional epoxy compound.
In a preferred embodiment of the present invention, the monofunctional epoxy compound is represented by formula (I):
where R denotes a substituent represented by R
1
-, R
2
—OCH
2
—or R
2
—COO—CH
2
—, R
1
denotes a hydrocarbon group having at least 2 carbon atoms, or CH
2
Cl, and each R
2
denote a hydrocarbon group having at least 4 atoms.
The present invention also provides a method of producing water-insolubilized regenerated collagen fiber, which comprises treating a regenerated collagen fiber with a water-insolubulizing agent comprising an epihalohydrin, and a sulfur compound.
Further, the present invention provides a method of producing a water-insolubilized regenerated collagen fiber, which comprises subjecting the water-insolubilized collagen fiber obtained by any of the methods noted above to an amidation reaction, in the presence of a condensing agent, with at least one diamine compound selected from the group consisting of a diamine having a disulfide linkage represented by formula (II):
H
2
N(CH
2
)
n
SS(CH
2
)
n
NH
2
(II)
where n denotes an integer of 1 to 4, or its salt, and a diamine having a disulfide linkage represented by formula (III):
H
2
NCH(OOR
1
)CH
2
SSCH
2
CH(OOR
2
)NH
2
(III)
where each of R
1
and R
2
independently represents an alkyl group having 1 to 4 carbon atoms or benzyl group.
Additional objects and advantages of the invention will be set forth in the description which follows, and in part will be obvious from the description, or may be learned by practice of the invention. The objects and advantages of the invention may be realized and obtained by means of the instrumentalities and combinations particularly pointed out hereinafter.
REFERENCES:
patent: 0548946A (1993-06-01), None
patent: 0 890 663 A2 (1999-01-01), None
Sung et al., Studies on Epoxy Compound Fixation, J. Biomed. Materials Res. (Applid Biomaterials), 33:177-186 (1996).
Goto Masaoki
Matsumura Kunihiko
Sakashita Shinichi
Christensen O'Connor Johnson & Kindness PLLC
Kaneka Corporation
Low Christopher S. F.
Tu Stephen
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