Method for producing compositions and complexes

Abstract

To provide a composition that can dye hair sufficiently even when using biological raw material, and a method for producing a complex included in the composition.SOLUTION: A composition includes dye particles derived from ink of a cephalopod organism, and a chitin derivative of biological origin. The dye particles and the chitin derivative form a complex. The complex is charged positive. The content of the dye particles is at most 24 times the content of the chitin derivative in terms of mass ratio.SELECTED DRAWING: Figure 3

Description

Technical Field

[0004] ,

[0001] The present invention relates to a method for producing a composition and a composite.

Background Art

[0002] Among the needs from the beauty industry such as beauty salons and beauty parlors, there are highly safe organic cosmetics. Especially regarding hair dyes, there are many reports of skin troubles caused by highly irritating drugs, so natural-derived low-irritant hair dyes and hair coloring materials are desired. As natural-derived coloring pigments, for example, mineral pigments such as clay, gardenia pigment, turmeric pigment, annatto pigment, copper chlorophyll sodium, paprika pigment, lac pigment, and other natural dyes are known.

[0003] Among the above-mentioned natural-derived pigments, bio-derived pigments are expected to cause less irritation to the human body because of their high biocompatibility. As bio-derived pigments, for example, squid ink pigment extracted and purified from the ink sac of squid can be mentioned. In order to use squid ink pigment in a wide range of applications, various attempts have been made so far. For example, Patent Document 1 discloses that squid ink pigment particles are refined to 100 nm or less and effectively used as a pigment or a dye.

[0004] Squid ink pigment particles are bio-derived edible black pigments and have excellent color fastness, light fastness, and heat resistance. Utilizing such functions of squid ink pigment particles, application development to organic cosmetics represented by hair coloring materials has been expected.

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0006] While bio-derived pigments such as squid ink possess resistance to discoloration, fading, and heat, and are highly biocompatible, they have not been used in organic cosmetics until now. One reason for this is that the surface of squid ink pigment is negatively charged, causing it to repel hair electrically and preventing sufficient dyeing.

[0007] Therefore, the object of the present invention is to provide a composition that can sufficiently dye hair even when using biologically derived raw materials, and a method for producing the complex contained in this composition. [Means for solving the problem]

[0008] Incidentally, examples of positively charged biological substances include chitin derivatives such as chitosan. Since chitin derivatives, which are polysaccharides, become colorless and transparent when dissolved in water, they have been used in organic cosmetics until now.

[0009] The present inventors have discovered that by using chemical synthesis techniques to bond a chitin derivative having both an amino group terminus and a positively charged (cationic) terminus with squid ink pigment particles, the surface of the squid ink pigment particles can be positively charged, and that these squid ink pigment particles can be applied to organic cosmetics such as hair dyes, thus completing the present invention. The gist of the present invention is as follows.

[0010] [1] A composition comprising pigment particles derived from the ink of cephalopods and a chitin derivative derived from an organism, The dye particles and the chitin derivative form a complex, A composition characterized in that the composite is positively charged. [2] The composition according to [1], wherein the dye particles are negatively charged. [3] The composition according to [1] or [2], wherein the chitin derivative is positively charged. [4] The composition according to any one of [1] to [3], wherein the chitin derivative has an amino group. [5] The composition according to any one of [1] to [4], wherein the cephalopod is a squid. [6] The composition according to any one of [1] to [5], wherein the chitin derivative is derived from a crustacean organism. [7] The composition according to any one of [1] to [6], wherein the amount of the pigment particles is 0.1 to 24 times the amount of the chitin derivative by mass. [8] A composition used for dyeing hair, as described in any one of items [1] to [7]. [9] A method for producing a composite in which dye particles and a chitin derivative are bound, The process includes a step of reacting the carboxyl group of the dye particles with the amino group of the chitin derivative using an activated esterification method. A method for manufacturing a composite, wherein the composite is positively charged. [Effects of the Invention]

[0011] According to the present invention, it is possible to provide a composition that can sufficiently dye hair even when using biologically derived raw materials, and a method for producing the complex contained in this composition. [Brief explanation of the drawing]

[0012] [Figure 1] This is a conceptual diagram for manufacturing the composite contained in the composition of the present invention. [Figure 2] These are photographs that serve as substitutes for drawings, showing the composition before and after electrophoresis. Figure 2(A) shows the composition of Production Example 1 before electrophoresis, and Figure 2(B) shows the composition of Production Example 1 after electrophoresis. Figure 2(C) shows the composition of Comparative Production Example 1 before electrophoresis, and Figure 2(D) shows the composition of Comparative Production Example 1 after electrophoresis. [Figure 3] These are photographic representations of the results of hair dyeing using the compositions of Examples 1 and 2 and Comparative Examples 1 and 2, along with the bleached hair before dyeing. [Modes for carrying out the invention]

[0013] <Composition> The composition of the present invention contains pigment particles derived from the ink of cephalopod organisms and a chitin derivative derived from organisms. Preferably, it contains a complex of negatively charged pigment particles and a chitin derivative having a site capable of binding to the pigment particles. In the present invention, it is preferable that a positively charged chitin derivative binds to the pigment particles and the complex is positively charged as a whole.

[0014] (Pigment particles) The pigment particles in the present invention are derived from the ink of cephalopod organisms. Examples of cephalopod organisms include squid, octopus, cuttlefish, and nautilus. Among them, squid is preferable from the viewpoints of easy availability, easy handling, and effective utilization of waste. Specifically, pigment particles extracted and purified from the ink sacs of Japanese flying squid, arrow squid, bigfin reef squid, red squid, and jumbo flying squid are included, but not limited thereto.

[0015] The main component of the pigment particles derived from the ink of cephalopod organisms is melanin pigment. Such pigment particles have excellent discoloration resistance, fade resistance, and heat resistance, and have been conventionally expected to be applied to hair dyeing. However, hair becomes negatively charged by being damaged by perms, hair coloring, ultraviolet rays, etc. Also, pigment particles extracted and purified from the ink sacs of cephalopod organisms are generally negatively charged. Then, due to electrostatic interaction, the hair and the pigment particles repel each other, and the pigment particles do not adsorb and penetrate into the hair. As a result, the hair does not get dyed with the pigment particles. Thus, it has been difficult to directly use the pigment particles derived from the ink of cephalopod organisms for hair dyeing. In the present invention, the surface of the pigment particles is positively charged by forming a complex with the chitin derivative described later. Then, the complex is positively charged as a whole. The positively charged complex and the negatively charged hair can be attracted by electrostatic interaction. As a result, the complex has excellent affinity and adsorptivity to the hair. In this way, the pigment particles can be adsorbed and penetrate into the hair by becoming a complex, and the hair can be dyed with the composition of the present invention.

[0016] (Chitin derivative) The chitin derivative in the present invention is derived from organisms. Since crustaceans are organisms rich in chitin, it is preferable that the chitin derivative is derived from crustaceans. Examples of crustaceans include crabs, shrimps, squids, daphnia, krill, and pill bugs. Among them, crabs are preferred from the viewpoints of easy availability, easy handling, and effective utilization of waste. Specifically, chitin extracted from the exoskeletons of snow crabs, red snow crabs, and king crabs can be mentioned, but it is not limited thereto.

[0017] The chitin derivative is a polysaccharide produced by chemical modification of chitin. Specific examples of chitin derivatives include chitosan, alkali chitin, N-allyl chitosan, N-alkyl chitosan, O-allyl chitosan, O-alkyl chitosan, sulfated chitosan, nitrated chitosan, carboxymethylated chitosan, tosylated chitosan, benzoylated chitosan, and phosphoric acid esterified chitin. Among them, chitosan is preferred.

[0018] Chitosan is a deacetylated product obtained by heating chitin in a concentrated alkaline solution (for example, an aqueous sodium hydroxide solution). When the deacetylation degree of pure chitin is set to 0% and the acetylation degree of pure chitosan is set to 100%, the deacetylation degree can be expressed as the percentage of chitosan units in a single polymer. When using chitosan, the deacetylation degree can be appropriately selected according to the solubility in the solvent and the use of the composite. In particular, as the chitin derivative, chitosan with a deacetylation degree of preferably 50% or more and 100% or less, more preferably 75% or more and 100% or less, and still more preferably 85% or more and 100% or less can be used. / / Note: There are no new line breaks added here as per the instruction.

[0019] From the viewpoint of being easily electrically bonded to pigment particles, it is preferable that the chitin derivative is positively charged. The aforementioned chitosan is a representative example of a positively charged chitin derivative. Chitosan is a polysaccharide in which -NHCOCH3 is converted to an amino group (-NH2) by deacetylation of chitin, and since the amino group is likely to carry a positive charge, it is positively charged.

[0020] Furthermore, it is preferable that the chitin derivative is transparent. By using a transparent chitin derivative, even if the chitin derivative binds to the pigment particles to form a complex, the hair will be more easily dyed by the color of the pigment particles.

[0021] (complex) The pigment particles and the chitin derivative form a complex. The bonds forming the complex can be chemical or electrical, and any known bond can be used without particular limitation. Furthermore, pigment particles extracted from cephalopods often contain not only melanin pigment but also proteins and other substances. Therefore, chitin derivatives may bind to the melanin pigment in the pigment particles, or they may bind to the proteins in the pigment particles.

[0022] Figure 1 shows a conceptual diagram for producing the complex contained in the composition of the present invention. Natural pigment particles extracted and purified from the ink sac of cephalopods (e.g., squid) generally have a negatively charged surface, as shown in Figure 1(A). By chemically or electrically bonding a positively charged chitin derivative to these particles, the surface of the pigment particles becomes positively charged, as shown in Figure 1(B). In Figure 1, chitosan is shown as a specific example of a chitin derivative. A specific example of a chemical bond is the amide bond formed between the carboxyl group of the pigment particle and the amino group of the chitin derivative. Details on how to form the amide bond will be described later.

[0023] As a result of the bonding between the pigment particles and the chitin derivative, the composite is positively charged. Therefore, the composite can adsorb to negatively charged substances and materials. In particular, adsorption can occur via the chitin derivative attachment sites present on the surface of the composite. The substances and materials to which the composite can adsorb are not particularly limited as long as they are negatively charged, and examples include human or animal hair or fibers.

[0024] Whether a complex is positively charged or not can be confirmed by subjecting the complex to electrophoresis. Electrophoresis is a phenomenon in which charged colloidal particles move in response to an applied electric field in a solution, and it is widely used in research to investigate the charge of colloidal particles. Alternatively, whether a complex is positively charged or not can also be confirmed by measuring its zeta potential. Specifically, this can be confirmed by the method described in the examples.

[0025] The pigment particle content is preferably 24 times or less by mass ratio to the chitin derivative content, more preferably 20 times or less, and even more preferably 15 times or less. By limiting the amount of pigment particles to a certain level relative to the chitin derivative, a sufficient amount of chitin derivative can be bound to the pigment particles. That is, even if the surface of the pigment particles is negatively charged, the positively charged chitin derivative can create a positively charged composite as a whole. As a result, the composite can be strongly adsorbed to hair, making it suitable for hair dyeing. The pigment particle content is preferably 0.1 times or more, more preferably 1 time or more, and even more preferably 3 times or more, in terms of mass ratio to the chitin derivative content. Having a certain amount of pigment particles relative to the chitin derivative allows for sufficient hair dyeing. Furthermore, the shade of the dyed hair can be adjusted by changing the ratio of pigment particles to chitin derivatives.

[0026] The composition of the present invention, containing such a complex, can be used particularly effectively for dyeing human or animal hair. Furthermore, known methods can be used without particular limitation for adsorbing and penetrating the complex into the hair.

[0027] When used for dyeing human or animal hair, the complex specifically adsorbs to the hair and does not penetrate the skin or scalp. In the complex contained in the composition of the present invention, both the pigment particles and the chitin derivative are of biological origin, so it causes almost no irritation to the skin or scalp and reduces damage to the hair.

[0028] <Method for manufacturing the composite> The composites contained in the composition of the present invention can be produced by chemically or electrically bonding pigment particles and a chitin derivative. The method of chemical bonding is not particularly limited. For example, it is preferable to bond them using an activated esterification method in order to increase reactivity. That is, it is preferable to react the carboxyl group of the pigment particle with the amino group of the chitin derivative to form an amide bond.

[0029] In the activated esterification method, the carboxyl groups of the pigment particles are activated with an activator, and then the activated pigment particles are condensed with a chitin derivative, thereby allowing the activated ester portion and the amino group portion to bond. The activation and condensation in the activated esterification method can be carried out in a suitable liquid medium. Examples of liquid media include water, aqueous buffers (e.g., acidic buffers), and organic solvents.

[0030] Examples of activators include N-hydroxysuccinimide (NHS), N-hydroxypolycarboxylic acid imides such as n-hydroxy-5-norbornene-2,3-dicarboxylic acid imide (HONB), N-hydroxytriazoles such as 1-hydroxybenzotriazole (HOBt), N-hydroxytriazines such as 3-hydroxy-4-oxo-3,4-dihydro-1,2,3-benzotriazine (HOOBt), 2-hydroxyimino-2-cyanoethyl acetate, and pentafluorophenol. Among these, NHS is preferred.

[0031] When NHS is used as an activator, the carboxyl groups of the dye particles first react with the NHS to produce an NHS ester. Next, the amino groups of the chitin derivative react with the NHS ester to form an amide bond, and the NHS is eliminated. As a result, a complex is obtained in which the dye particles and the chitin derivative are chemically bonded by an amide bond.

[0032] Examples of condensing agents include carbodiimide-based condensing agents such as diisopropylcarbodiimide (DIPC), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDAC), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC), and dicyclohexylcarbodiimide (DCC). Among these, WSC is preferred.

[0033] Pigment particles derived from the ink of cephalopods generally contain melanin pigment and protein. The carboxyl group activated by the activator may be one present in the melanin pigment or one present in the protein. Alternatively, carboxyl groups present in other components of the pigment particles may be activated.

[0034] The dye particles and the chitin derivative may be electrically bonded rather than chemically bonded. For example, negatively charged dye particles and positively charged chitin derivatives may be mixed and attracted to each other by electrostatic interaction.

[0035] <Application> The above-described complex can be suitably used as a hair dye or a pigment for hair dyes. When used as a pigment for hair dyeing, it may be used in combination with other natural dyes or pigments. Examples of natural pigments include mineral pigments such as clay, natural dye lakes such as madder lake and cochineal lake, azo pigments, phthalocyanine pigments, and metal powders. Examples of natural dyes include gardenia pigment, turmeric pigment, annatto pigment, copper chlorophyllin sodium, paprika pigment, and lac pigment.

[0036] Compositions using the above-mentioned complex as a hair dye or pigment for hair dyes may optionally contain oily components, surfactants, polymer compounds, vitamins, antioxidants, fragrances, bactericidal / preservatives, anti-inflammatory agents, UV absorbers, propellants, thickeners, etc. Various well-known or recognized components may be used as desired.

[0037] Examples of oily components include hydrocarbons, polyhydric alcohols, oils and fats, higher alcohols, higher fatty acids, alkyl glyceryl ethers, esters, and silicones. These can be blended individually or in combination of two or more types.

[0038] Examples of surfactants include cationic surfactants, nonionic surfactants, anionic surfactants, and amphoteric surfactants. These can be formulated individually or in combination of two or more types.

[0039] Examples of polymer compounds include cationic polymers, anionic polymers, amphoteric polymers, nonionic polymers, and natural polymers. Examples of cationic polymers include cationized cellulose derivatives such as polyquaternium-10, cationized guar gum, and diallyl quaternary ammonium salt / acrylamide copolymers such as polyquaternium-7. Examples of anionic polymers include carboxyvinyl polymers (carbomers). Examples of amphoteric polymers include diallyl quaternary ammonium salt / acrylic acid copolymers such as polyquaternium-39. Examples of nonionic polymers include cellulosic polymers such as methylcellulose, ethylcellulose, and hydroxyethylcellulose, polyvinylpyrrolidone polymers such as PVP and PVP / VA copolymers, and alginic acid polymers such as sodium alginate. Examples of natural polymers include plant-derived polymers such as gum arabic, xanthan gum, carrageenan, pectin, and agar, microbial polymers such as dextran and pullulan, animal-derived polymers such as collagen, casein, and gelatin, and alginic acid polymers such as sodium alginate.

[0040] When the complex is used as a hair dye or a pigment for hair dyes, the dosage form of the composition is not particularly limited, but examples include liquid, emulsion (water-in-oil emulsion, oil-in-water emulsion, multi-layer emulsion), powder, tablet, gel, foam, etc. In the case of a foam dosage form, it can be made foamy using a known foaming tool. Examples of known foaming tools include non-aerosol foamers, aerosol foamers, shakers, etc. In the case of an aerosol foamer, a known propellant and foaming agent can be used. In the case of a solid dosage form, a dispersant may be added to the hair dye composition.

[0041] Of these formulations, it is preferable that the formulation be in an emulsified or foamy state when used, from the viewpoint of excellent handling and improved hair dyeing performance by adhering closely to the hair, and from the viewpoint of formulation stability, it is more preferable that the formulation be in an emulsified state when used. [Examples]

[0042] The present invention will now be described in more detail with reference to examples, but the present invention is not limited to these examples.

[0043] [Manufacturing Example 1] Production of a composition containing a complex in which dye particles and a chitin derivative are chemically bonded. N-hydroxysuccinimide (NHS) was dissolved in an acidic buffer (Activation Buffer, manufactured by Dojin Chemical Laboratories, pH 4.4 to 4.6) to prepare an NHS solution with a concentration of 100 mM. Furthermore, a WSC solution was prepared by dissolving 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) in an acidic buffer (Activation Buffer, pH 4.4 to 4.6, manufactured by Dojin Chemical Laboratories) to a concentration of 100 mM. A suspension containing 50 g / L of pigment particles extracted from the ink sac of a cuttlefish was prepared. To 4 μL of this suspension, 100 μL of the above WSC solution, 100 μL of the above NHS solution, and 100 μL of acidic buffer (Activation Buffer, pH 4.4 to 4.6, manufactured by Dojin Chemical Laboratories) were added, and the mixture was allowed to stand at 20-25°C for 1 hour. In this way, the carboxyl groups of the pigment particles were converted into reactive NHS esters. Subsequently, 200 μL of a chitin derivative solution containing 10 g / L of chitosan extracted from the crab exoskeleton was added to adjust the final concentration of the pigment particles to approximately 0.4 g / L. The resulting solution was allowed to stand for 1 hour at a temperature between 20°C and 25°C, thereby bonding the NHS ester of the pigment particles with the amino group of the chitin derivative via amide bonds, forming a complex. In this way, a composition containing the complex was prepared. In this composition, the pigment particle content was 0.1 times the mass ratio of the chitin derivative content.

[0044] [Comparative Manufacturing Example 1] Manufacturing of a composition containing pigment particles The composition was prepared in the same manner as in Production Example 1, except that 200 μL of the solvent for the chitin derivative solution was used instead of 200 μL of the chitin derivative solution.

[0045] <Electrophoresis> The surface charge of the composite in Production Example 1 and the dye particles in Comparative Production Example 1 was confirmed by electrophoresis. The compositions obtained in Production Example 1 and Comparative Production Example 1 were each placed in cellulose tubes, and both ends were secured with clips. The cellulose tubes were submerged in an electrophoresis layer filled with Tris-acetate EDTA buffer. Two glass slides were placed on top to prevent the cellulose tubes from floating. Electrophoresis was performed by applying a voltage of 100V for 1 hour. Figure 2 shows the state before and after electrophoresis. As shown in Figure 2(A), the composite in Production Example 1 was uniformly dispersed in the cellulose tube before electrophoresis. As a result of electrophoresis, as shown in Figure 2(B), the black composite moved to the cathode side (right side in Figure 2(B)). On the other hand, in comparative production example 1, the dye was uniformly dispersed in the cellulose tube before electrophoresis, as shown in Figure 2(C). As a result of electrophoresis, as shown in Figure 2(D), the black dye particles migrated to the anode side (left side in Figure 2(D)). These results indicate that the dye particles in comparative manufacturing example 1 had a negatively charged surface, while the composite in manufacturing example 1 had a positively charged surface.

[0046] [Manufacturing Example 2] Production of a composition containing a composite in which dye particles and a chitin derivative are electrically bonded. 8 μL of the suspension used in Production Example 1 was mixed with 3.2 mL of water and stirred. Then, 400 μL of the chitin derivative solution used in Production Example 1 was added to adjust the final concentration of the pigment particles to approximately 0.1 g / L. The resulting solution was stirred to electrically attract the negatively charged pigment particles and the positively charged chitin derivative, forming a complex. In this way, a composition containing the complex was prepared. In this composition, the pigment particle content was 0.1 times the mass ratio of the chitin derivative content.

[0047] [Comparative Manufacturing Example 2] Manufacturing of a composition containing pigment particles The composition was prepared in the same manner as in Production Example 2, except that 400 μL of the solvent for the chitin derivative solution was used instead of 400 μL of the chitin derivative solution.

[0048] <Measuring Zeta Potential> The zeta potential of the composite in Production Example 2 and the dye particles in Comparative Production Example 2 was measured using the analytical instrument "Zetasizer Nano ZS ZEN3600" (Malvern), and the surface charge was confirmed. In the composition of Production Example 2, a positive value of +57.9 mV was obtained for the zeta potential of the complex. On the other hand, in the composition of comparative manufacturing example 2, a negative value of -26.3mV was obtained for the zeta potential of the dye particles. These results indicate that the dye particles in comparative manufacturing example 2 had a negatively charged surface, while the composite in manufacturing example 2 had a positively charged surface.

[0049] [Example 1] The suspension used in Production Example 1, an acidic buffer (Dojin Chemical Laboratories, Activation Buffer, pH 4.4 to 4.6), and the chitin derivative solution used in Production Example 1 were mixed in a volume ratio of 14:79:7 to adjust the final concentration of pigment particles to 7 g / L. The resulting solution was stirred to prepare the composition of Example 1. In the composition of Example 1, the amount of pigment particles was 10 times the amount of chitin derivative by mass. That is, the ratio of the mass of pigment particles to the mass of chitin derivative was 10:1.

[0050] [Example 2] The composition of Example 2 was prepared in the same manner as in Example 1, except that the mixing ratio of the suspension, the acidic buffer, and the chitin derivative solution was 7:36:7 by volume. The final concentration of the dye particles was 7 g / L. In the composition of Example 2, the amount of pigment particles was 5 times the amount of chitin derivative by mass. That is, the ratio of the mass of pigment particles to the mass of chitin derivative was 5:1.

[0051] [Comparative Example 1] The composition of Comparative Example 1 was prepared in the same manner as in Example 1, except that the mixing ratio of the suspension, the acidic buffer, and the chitin derivative solution was 7:43:0 by volume. The final concentration of the dye particles was 7 g / L. The composition of Comparative Example 1 did not contain a chitin derivative. That is, the ratio of the mass of the dye particles to the mass of the chitin derivative was 1:0.

[0052] [Comparative Example 2] The composition of Comparative Example 2 was prepared in the same manner as in Example 1, except that the mixing ratio of the suspension, the acidic buffer, and the chitin derivative solution was 35:208:7 by volume. The final concentration of the dye particles was 7 g / L. In the composition of Comparative Example 2, the amount of pigment particles was 25 times the amount of chitin derivative by mass. That is, the ratio of the mass of pigment particles to the mass of chitin derivative was 25:1.

[0053] <Hair dyeing test> 1.3 mL of the compositions obtained in Examples 1 and 2 and Comparative Examples 1 and 2 were applied to bleached hair. After being left at room temperature for 30 minutes, the compositions were rinsed off with water, and the hair dyeing process was observed. The results, along with those of the bleached hair before dyeing, are shown in Figure 3.

[0054] As shown in Figure 3, the composition of Comparative Example 1, which did not contain a chitin derivative, and the composition of Comparative Example 2, which contained an extremely small amount of chitin derivative relative to the pigment particles, were hardly able to dye the bleached hair. This is thought to be because the surface of the pigment particles or complex was negatively charged, and the pigment particles or complex and the negatively charged bleached hair were electrically repelled. On the other hand, in the compositions of Examples 1 and 2, which contained a certain amount of chitin derivatives relative to the pigment particles, bleached hair could be dyed black or brown. This is because the surface of the complex became positively charged, and the complex and the negatively charged bleached hair were electrically attracted to each other and strongly adsorbed. Furthermore, the composition of Example 1 was able to dye bleached hair black, and the composition of Example 2 was able to dye bleached hair brown. In other words, it was found that the shade of dyed hair can be adjusted by adjusting the mixing ratio of pigment particles and chitin derivatives.

Claims

1. A composition comprising pigment particles derived from the ink of cephalopods and chitosan derived from organisms, The dye particles and the chitosan form a complex, The amount of the pigment particles is 1 to 15 times the amount of chitosan by mass ratio. A composition characterized in that the composite is positively charged.

2. The composition according to claim 1, wherein the dye particles are negatively charged.

3. The composition according to claim 1 or 2, wherein the chitosan is positively charged.

4. The composition according to any one of claims 1 to 3, wherein the carboxyl group of the pigment particle and the amino group of the chitosan are bonded by an amide linkage.

5. The composition according to any one of claims 1 to 4, wherein the cephalopod is a squid.

6. The composition according to any one of claims 1 to 5, wherein the chitosan is derived from a crustacean organism.

7. A composition used for dyeing hair, according to any one of claims 1 to 6.

8. A method for producing a complex in which pigment particles and chitosan are bound together, The process includes a step of reacting the carboxyl group of the dye particles with the amino group of the chitosan using an activated esterification method. The amount of the pigment particles is 1 to 15 times the amount of chitosan by mass ratio. A method for manufacturing a composite, wherein the composite is positively charged.

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