Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B63/00—Lakes
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/0097—Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with dyes
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
  • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
  • C09C1/40—Compounds of aluminium
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
  • C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
  • C09C3/08—Treatment with low-molecular-weight non-polymer organic compounds

Definitions

• the present invention relates to a water-insoluble dye composition.
• caramel-based pigments are water-soluble, and when used in cosmetics and food pigments, it has been found that they are likely to cause problems such as elution in water and accompanying discoloration. Therefore, it is currently used only in very limited applications.
• the present invention provides a water-insoluble caramel colorant composition, and food, cosmetics, pharmaceuticals or agricultural chemicals containing the colorant composition, coating materials or printed markers, stationery, writing instruments, printing inks, inkjet inks, metallic inks, and paints. , plastic colorants, or color toners.
• the present inventors have found that a water-insoluble dye composition in which a caramel-based dye is coated, impregnated, complexed, or adsorbed on a metal or metal compound is soluble in water.
• the present inventors have found that the water-insoluble dye composition is insoluble and that the water-insoluble dye composition can be used as a coloring agent in a variety of applications, thereby completing the present invention.
• a water-insoluble dye composition according to 1, wherein the caramel dye and the metal or metal compound are in a weight ratio of caramel dye:metal or metal compound 0.1:99.9 to 90:10.
• the water-insoluble coloring matter composition according to 1 or 2 wherein the caramel coloring matter is caramel I, caramel II, caramel III, or caramel IV.
• caramel colorant used in the present invention is a mixture of multiple compounds produced by heating carbohydrates, but the production mechanism has not been completely elucidated, and it contains polymerized furan and tetramolecularly dehydrated glucose. It is believed that. By-products may include 4-methylimidazole and 2-acetyl-4-tetrahydroxybutyrimidazole. Caramel colorants are classified into caramel I colorant, caramel II colorant, caramel III colorant, and caramel IV colorant according to the manufacturing method, but all of them are readily soluble in water and insoluble in oils and fats and organic solvents. It is also stable against heat, light, and pH changes.
• Caramel-based pigments include caramel I pigment, caramel II pigment, caramel III pigment, and caramel IV pigment, but caramel I pigment refers to those made by heating only sugars. Caramel I pigment is more expensive than others, but is considered to be safer.
• Caramel II pigment is obtained by adding a sulfite compound to sugar and heating it.
• Caramel III pigment is obtained by adding an ammonium compound to sugars and heating them.
• Caramel IV dye is obtained by adding a sulfite compound and an ammonium compound to sugars and heating them.
• caramel colorants in general can be used, but caramel I colorant, caramel III colorant, and caramel IV colorant are particularly preferable in terms of safety, color development, and insolubility.
• metals, metal compounds Any metal or metal compound can be used as long as it has a supporting action for insolubilizing the caramel colorant. They are simple metals, metal oxides, metal hydroxides, and the like, and aluminum, aluminum oxides, and aluminum hydroxides can be preferably used.
• the metal elements in the metals or metal compounds used in the present invention include those belonging to Groups 1 to 15 of the periodic table, excluding those belonging to the first period and the second period. Among them, metal elements such as iron, cobalt, nickel, zinc, aluminum, and titanium can be used, and one or more metal elements selected from them can be used.
• Metals or metal compounds that have no effect on the human body are particularly preferred for use in foods and cosmetics, and aluminum, titanium, and zinc are particularly preferred in the embodiment of the present invention.
• metal hydroxides and oxides are preferably used as metals or metal compounds in order to further strengthen the physical adsorption of caramel-based pigments and metals or metal compounds, particularly aluminum hydroxide.
• titanium oxide and zinc oxide are preferably used. Physical adsorption with caramel pigments is better when alkali is added to chlorides such as aluminum chloride, titanium tetrachloride, and zinc chloride, and a slurry of aluminum hydroxide, titanium oxide, zinc hydroxide, etc. is used. Be strong and be favorable.
• the surface of the metal or metal compound is coated with a caramel-based dye.
• the definition of the coating and the particle size of the metal compound particles vary depending on the application, and the hue also varies depending on the particle size of the metal or metal compound particles. For example, it is preferably 100 nm to 20 ⁇ m for food and cosmetic applications, and 50 to 500 nm for other applications.
• metal compounds also exhibit large changes in particle charge with pH changes in aqueous solutions. Therefore, by adjusting the pH of the aqueous dispersion of these two substances, the metal compound and the caramel-based pigment are physically adsorbed by electrical interaction, precipitated as a complex, and are insoluble in water.
• caramel-based pigments which have been limited to food and cosmetic applications, can be used as coloring materials equivalent to ordinary pigments as coating materials for foods, cosmetics, pharmaceuticals, or agricultural chemicals, or printing markers, stationery, and writing instruments. , printing ink, inkjet ink, metal ink, paint, plastic colorant, or color toner. Moreover, along with the insolubilization, an improvement in properties such as heat resistance and light resistance can be expected.
• the uses of the water-insoluble dye composition of the present invention are not limited to the uses described above.
• the caramel colorant:metal or metal compound 0.1:99.9 to 90:10.
• Method for producing water-insoluble dye composition As a method for producing the water-insoluble coloring matter composition of the present invention, a method of mixing a caramel-based coloring matter and a metal or a metal compound in a solvent is preferable because the most uniform water-insoluble coloring matter composition can be produced.
• a method for producing a water-insoluble dye composition by mixing each substance in a solvent, 1) first, a metal or metal compound is dissolved in a dilute aqueous acid solution to prepare a solution. 2) On the other hand, a caramel colorant or a preparation containing a caramel colorant is dissolved in water to prepare an aqueous solution. 3) Next, the above two liquids are mixed to prepare a mixed liquid. 4) Further, a pH adjuster is added to the mixed solution to adjust the pH to prepare a mixed solution containing the water-insoluble dye composition. 5) A method of filtering and drying the resulting mixture containing the water-insoluble dye composition can be mentioned.
• the metal or metal compound solution may be mixed with the caramel colorant-containing aqueous solution, or the caramel colorant may be mixed as it is in powder form.
• the metal or metal compound solution may be mixed with the caramel-based dye-containing aqueous solution, or these two liquids may be mixed little by little.
• the metal or metal compound solution may be a state in which the metal or metal compound is completely dissolved in the liquid, or the metal or metal compound is partially dissolved in the liquid and partially dispersed in the liquid. It's okay.
• the temperature for mixing may be room temperature or may be heated.
• the mixing temperature is preferably 10 to 60°C, more preferably 20 to 50°C.
• the pH range for mixing the metal or metal compound solution and the caramel colorant-containing aqueous solution is preferably 2.0 to 6.0, more preferably 3.0 to 5.0.
• Aqueous solutions such as sodium hydroxide and potassium hydroxide can be used as pH adjusters when adjusting the pH.
• the pH range of the mixed liquid when the pH adjuster is added is preferably 6.0 to 8.5 from the viewpoint of efficiently adsorbing and insolubilizing the metal or metal compound and the caramel colorant in the mixed liquid. It is more preferable to adjust to 0.5 to 8.0.
• the resulting mixture containing the water-insoluble dye composition can be filtered and dried to obtain the water-insoluble dye composition.
• the mixed solution is filtered through a filter such as Nutsche, and the wet cake is repeatedly washed with water. Since the filtrate is not colored and the wet cake is colored, it can be confirmed that the caramel-based coloring matter and the metal or metal compound are adsorbed.
• the resulting water-insoluble wet cake of the water-insoluble dye composition is dried at room temperature, by heating, in vacuum, under reduced pressure, or the like, to obtain a dry water-insoluble dye composition.
• the drying method and the dryer are not limited as long as they are ordinary methods and devices.
• the water-insoluble dye composition of the present invention can be used properly depending on the application whether it is a wet cake containing water or a dry dry water-insoluble dye composition.
• the wet cake can be used as it is, and when used in solvent-dispersed systems, it can be used after replacing the water-based with solvent-based.
• the dry water-insoluble dye composition can be used as it is, or it can be used after being redispersed in water, an organic solvent, a resin solution, or the like.
• stabilizer additive
• Stabilizers and additives can also be added to the water-insoluble dye composition of the present invention in order to further impart light resistance and heat resistance.
• the stabilizer and additive can be added to each or both of the metal hydroxide aqueous solution and the caramel-based pigment-containing aqueous solution, or they can be added to the prepared water-insoluble pigment composition.
• the water-insoluble dye composition of the present invention can be mixed with other resins, rubbers, additives, pigments, dyes, etc., if necessary, to form the final coating material for food, cosmetics, pharmaceuticals or agricultural chemicals, printing markers, stationery. , writing instruments, printing inks, inkjet inks, metal inks, paints, plastic coloring agents, color toners, etc. An example of the above application is shown below.
• the water-insoluble dye composition of the present invention can be used as cosmetics.
• the cosmetics used are not particularly limited, and the water-insoluble dye composition of the present invention can be used in various types of cosmetics.
• the cosmetics may be of any type as long as they can effectively exhibit their functions.
• the cosmetics may be lotions, cream gels, sprays and the like.
• Examples of the cosmetics include skin care cosmetics such as face wash, makeup remover, lotion, serum, face pack, protective milky lotion, protective cream, whitening cosmetics, and UV protection cosmetics, foundation, white powder, makeup base, lipstick, eye makeup, Make-up cosmetics such as cheek rouge and nail enamel, hair care cosmetics such as shampoo, hair rinse, hair treatment, hair styling agents, permanent waving agents, hair dyes, and hair growth agents, body care cosmetics such as body wash cosmetics, deodorant cosmetics, and bath agents Cosmetics etc. can be mentioned.
• the amount of the water-insoluble dye composition of the present invention used in the cosmetics can be appropriately set according to the type of cosmetics.
• the content in the cosmetics is usually in the range of 0.1 to 99% by mass, and generally preferably in the range of 0.1 to 10% by mass.
• the amount is preferably in the range of 5 to 80% by mass, more preferably in the range of 10 to 70% by mass, and most preferably in the range of 20 to 60% by mass. is preferred.
• the amount of the water-insoluble dye composition of the present invention contained in the cosmetic product is within the above range, it is possible to effectively exhibit functions such as coloring properties, and to maintain the functions required of the cosmetic product. .
• the cosmetic may contain, in addition to the water-insoluble dye composition of the present invention, a carrier, pigment, oil, sterol, amino acid, moisturizer, powder, colorant, pH Regulators, fragrances, essential oils, cosmetic active ingredients, vitamins, essential fatty acids, sphingolipids, self-tanning agents, excipients, fillers, emulsifiers, antioxidants, surfactants, chelating agents, gelling agents, thickeners, Emollients, humectants, moisturizers, minerals, viscosity modifiers, rheology modifiers, keratolytics, retinoids, hormonal compounds, alpha hydroxy acids, alpha keto acids, antimycobacterials, antifungals, antibacterials, antivirals pain relievers, anti-allergic agents, antihistamines, anti-inflammatory agents, anti-irritants, antineoplastic agents, immune system boosters, immune system suppressants, anti-acne agents, anesthetics,
• a carrier pigment,
• the cosmetics can be prepared by mixing the water-insoluble pigment composition of the present invention and other cosmetic ingredients.
• Cosmetics containing the water-insoluble dye composition of the present invention can be used in the same manner as ordinary cosmetics, depending on the type of the cosmetic.
• the water-insoluble dye composition of the present invention can be used as inks and paints. However, the uses and compositions of inks and paints are described, but are not limited to these.
• the water-insoluble dye composition of the present invention may be dispersed only in a thermoplastic resin, but it can also be dispersed in a printing ink vehicle or paint vehicle containing a thermoplastic resin as an essential component.
• thermoplastic resins resins such as polyester resins, polyamide resins, styrene resins, acrylic resins, polyolefins, polyalkylene terephthalates, and polyvinyl chloride resins can be used as dispersing resins.
• the vehicle of the lithographic printing ink contains 20 to 50 (mass)% of resin such as rosin-modified phenolic resin, petroleum resin and alkyd resin, and 0 to 30 (mass) of animal and vegetable oil such as linseed oil, tung oil and soybean oil. %, n-paraffin, isoparaffin, naphthene, ⁇ -olefin, aromatic solvents at 10-60% (mass), and other additives such as solubilizers and gelling agents at several (mass)%. be done.
• resin such as rosin-modified phenolic resin, petroleum resin and alkyd resin
• animal and vegetable oil such as linseed oil, tung oil and soybean oil.
• other additives such as solubilizers and gelling agents at several (mass)%.
• rosins maleic acid resins, polyamide resins, vinyl resins, cyclized rubbers, chlorinated rubbers, ethylene-vinyl acetate copolymer resins, urethane resins, polyester resins, 10 to 50 (mass)% of one or more resin selected from alkyd resin, nitrocellulose, cellulose acetate, etc., 30 to 80 (mass) of solvent such as alcohol, toluene, n-hexane, ethyl acetate, cellosolve, butyl cellosolve, etc. % raw materials.
• solvent such as alcohol, toluene, n-hexane, ethyl acetate, cellosolve, butyl cellosolve, etc. % raw materials.
• Vehicles for paints include, for example, alkyd resins, epoxy resins, acrylic resins, polyurethane resins, polyester resins, melamine resins, urea resins, water-soluble resins, etc. 20 to 80 (mass)% of resins, hydrocarbons, alcohols, ketones It is manufactured from raw materials containing 10 to 60 (mass)% of solvent such as water.
• the water-insoluble dye composition of the present invention can also be used for plastic coloring applications.
• thermoplastic resins (plastics) for thermoforming such as injection molding and press molding, such as polyolefins such as polyethylene and polypropylene, and polyvinyl chloride resins, are used.
• the water-insoluble dye composition can be kneaded into these resins by a conventionally known method.
• the water-insoluble dye composition of the present invention can also be used for toner coloring applications.
• thermoplastic resins such as polyester resins, polyamide resins, styrene resins and acrylic resins, which are solid at room temperature and have film-forming properties, are used as dispersing resins.
• the toner for electrostatic image development produced using the water-insoluble dye composition of the present invention as a constituent component includes a one-component color magnetic toner (color toner for magnetic one-component development) containing a magnetic substance in the toner, and a magnetic toner containing a magnetic substance. It can be used as a non-magnetic one-component color toner (color toner for non-magnetic one-component development) that does not contain a carrier, or a color toner for a two-component color developer mixed with a carrier (color toner for two-component development).
• the one-component color magnetic toner can be composed of, for example, colorants, binder resins, magnetic powders, charge control agents (CCA), and other additives such as release agents, in the same manner as those commonly used.
• CCA charge control agents
• release agents in the same manner as those commonly used.
• the amount of the water-insoluble dye composition used in the toner for electrostatic charge image development is not particularly limited, but it is preferably used in a proportion of 0.5 to 25 parts by mass with respect to 100 parts by mass of the binder resin. It is more preferable that the amount is 4 to 10 parts by mass with respect to 100 parts by mass of the binder resin in order to make the charging performance of the binder more remarkable.
• thermoplastic resins any of the known and commonly used thermoplastic resins exemplified above can be used. Any of natural rubber, synthetic rubber, synthetic wax, etc. can be used.
• Example 1 46.4 g of aluminum (III) chloride hexahydrate (manufactured by Kanto Kagaku Co., Ltd.) was dissolved in 1000 mL of deionized water in a 2 L beaker. Subsequently, a 4.8% sodium hydroxide aqueous solution diluted from a 48% sodium hydroxide aqueous solution (manufactured by Kanto Kagaku Co., Ltd.) was added to adjust the pH to 4.0 to prepare an aluminum hydroxide slurry.
• aluminum (III) chloride hexahydrate manufactured by Kanto Kagaku Co., Ltd.
• caramel pigment I manufactured by Kanto Kagaku Co., Ltd.
• a 4.8% aqueous sodium hydroxide solution was added to adjust the pH to 7.0, followed by stirring for 30 minutes. .
• the filtered solid was dried in a vacuum dryer (740 mmHg) at 30° C. for 14 hours to obtain 15.3 g of powder (1).
• the resulting powder (1) exhibited a brown color similar to caramel color.
• dispersion liquid (1) After adding 10 mg of powder (1) and 1.0 g of water to a 10 mL vial, the mixture was stirred for 5 minutes to prepare dispersion liquid (1). When one drop of Dispersion (1) was dropped onto the filter paper, it was observed that the dropped portion turned brown in a circular shape, and then the colorless and transparent liquid spread concentrically. The portion that first turned brown in a circular shape was powder (1) that was insoluble in water, and then the portion where a transparent liquid spread concentrically was water, and powder (1) was insoluble in water. I found out.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Pigments, Carbon Blacks, Or Wood Stains (AREA)
• Inks, Pencil-Leads, Or Crayons (AREA)

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Publications (1)

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• 2022
  • 2022-09-15 JP JP2023551303A patent/JP7552927B2/ja active Active
  • 2022-09-15 WO PCT/JP2022/034506 patent/WO2023053983A1/ja not_active Ceased

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