Dispersant for pigment

Abstract

The present invention addresses the problem of providing a novel dispersant capable of satisfactorily dispersing a pigment, a pigment dispersion composition containing a pigment and a dispersant, and a method for dispersing a pigment. Provided are an amide alcohol-containing dispersant for a pigment, a pigment dispersion composition containing a pigment and said dispersant, and a method for dispersing a pigment.

Description

Pigment dispersants

[0001] The present invention relates to a pigment dispersant, a pigment dispersion method using such a dispersant, a pigment dispersion composition, and a method for producing a pigment dispersion composition.

[0002] Pigments are used to impart desired colors or as reinforcing agents in various products, such as cosmetics, paints, plastic products, and rubber. To perform their functions, pigments must be well dispersed. However, in various compositions, pigments can aggregate or precipitate.

[0003] To address these problems, the use of dispersants has been proposed, including a combination of lower alkanolamide and phosphate ester as a carbon black dispersant for rubber (Patent Document 1), amides as dispersants for fine powder materials (Patent Document 2), and amide alcohols with specific structures as dispersants for solid particles (Patent Document 3). However, the dispersibility of pigments and the resulting color development have not always been sufficient.

[0004] It is known that the amide alcohol of formula (I) in the present application can be used as a cosmetic base such as a thickener, a gelling agent, a moisturizer, and a hair dye improving agent (Patent Document 4), and can be used to prepare a stable emulsion composition in combination with a carboxyl group-containing polymer (Patent Document 5).

[0005] Japanese Patent Laid-Open No. 2-35929 Japanese Patent Laid-Open No. 2000-513025 Japanese Patent Laid-Open No. 2002-346362 WO2017 / 213177 Japanese Patent Laid-Open No. 2019-85544

[0006] An object of the present invention is to provide a new dispersant capable of dispersing a pigment well, a dispersion containing the pigment and the dispersant, and a method for dispersing a pigment, and further to provide an agent capable of improving the color development of a pigment in a dispersion, a pigment dispersion composition having improved color development, and a method for improving the color development of a pigment.

[0007] Through extensive research, the present inventors discovered that by incorporating an amide alcohol into the dispersion of a pigment, the color tone of the resulting dispersion can be improved and sedimentation of the pigment can be suppressed. As a result of further research, the present inventors have completed the present invention.

[0008] That is, the present invention relates to the following [1] to [8]. [1] Formula (I) In the formula R １ is a C6 to C22 hydrocarbon group, R ２ is H or a C6 to C22 hydrocarbon group, R ３ [2] A pigment dispersant containing an amide alcohol represented by the formula (I), wherein R １ is an amide alcohol having a C6 to C22 unsaturated and / or branched hydrocarbon group.

[0009] [3] (1) Formula (I) Formula (I) In the formula R １ is a C6 to C22 hydrocarbon group, R ２ is H or a C6 to C22 hydrocarbon group, R ３ (2) dissolving an amide alcohol represented by the following formula (1): wherein R is a linear or branched C2 to C21 hydrocarbon group in a solvent to obtain a mixture, and (3) mixing the pigment with the dispersion medium together with the mixture obtained in step (1) to dissolve the pigment. [4] The method according to [3], wherein the solvent in step (1) is hexyldecanol, isostearyl alcohol, and / or octyldodecanol.

[0010] [5] (A) Formula (I) In the formula R １ is a C6 to C22 hydrocarbon group, R ２ is H or a C6 to C22 hydrocarbon group, R ３[6] A pigment dispersion composition comprising: (A) an amide alcohol represented by the formula (I): In the formula R １ is a C6 to C22 hydrocarbon group, R ２ is H or a C6 to C22 hydrocarbon group, R ３ (B) a solvent selected from hexyldecanol, isostearyl alcohol, and octyldodecanol; (C) a dispersion medium; and (D) a pigment.

[0011] [7] (1) Formula (I) Formula (I) In the formula R １ is a C6 to C22 hydrocarbon group, R ２ is H or a C6 to C22 hydrocarbon group, R ３ (1) dissolving an amide alcohol represented by the formula (I) in a solvent, wherein R is a linear or branched C2 to C21 hydrocarbon group, to obtain a mixture, and (2) mixing a pigment together with the mixture obtained in step (1) with a dispersion medium and any other components to disperse the pigment. [8] The pigment dispersion composition according to item [7], wherein the solvent is hexyldecanol, isostearyl alcohol, and / or octyldodecanol.

[0012] [9] Formula (I) In the formula R １ is a C6 to C22 hydrocarbon group, R ２ is H or a C6 to C22 hydrocarbon group, R ３

[10] The pigment dispersion composition according to any one of [5] to [9], wherein the pigment is finely divided titanium oxide or finely divided zinc oxide.

[11] The pigment dispersion composition according to any one of [5] to [9], wherein the pigment is a finely divided titanium oxide or finely divided zinc oxide.

[12] The pigment dispersion composition according to any one of [5] to [9], wherein the pigment is a coating composition.

[13] The pigment dispersion composition according to any one of [5] to [9], wherein the pigment is a cosmetic composition.

[0013]

[13] A pigment represented by the formula (I) In the formula R １ is a C6 to C22 hydrocarbon group, R ２ is H or a C6 to C22 hydrocarbon group, R ３ is a linear or branched C2 to C21 hydrocarbon group, and a dispersion medium, and dissolving the resulting pigment dispersion composition in the dispersion medium.

[0014] By using the amide alcohol of formula (I) of the present application to disperse a pigment, it is possible to improve the dispersibility of the pigment and / or suppress the precipitation of the pigment, thereby providing a pigment dispersion composition with stable dispersion. Furthermore, by using the amide alcohol of formula (I) of the present application, it is also possible to provide a pigment dispersion composition with improved color tone of the pigment dispersion.

[0015] FIG. 1 is a diagram showing a color tone evaluation of SI-treated iron oxide (yellow pigment). FIG. 2 is a diagram showing a color tone evaluation of untreated iron oxide (yellow pigment). FIG. 3 is a diagram showing a color tone evaluation of SI-treated iron oxide (red pigment). FIG. 4 is a diagram showing a color tone evaluation of untreated iron oxide (red pigment). FIG. 5 is a diagram showing a color tone evaluation of SI-treated titanium (white pigment). FIG. 6 is a diagram showing a color tone evaluation of untreated iron oxide (white pigment). FIG. 7 is a diagram showing a color tone evaluation of SI-treated iron oxide (black pigment). FIG. 8 is a diagram showing a color tone evaluation of untreated iron oxide (black pigment). FIG. 9 is a diagram showing a color tone evaluation of carbon black.

[0016] Photographs and microscope images showing the dispersion state of SI-treated iron oxide (yellow pigment). Photographs and microscope images showing the dispersion state of untreated iron oxide (yellow pigment). Photographs and microscope images showing the dispersion state of SI-treated iron oxide (red pigment). Photographs and microscope images showing the dispersion state of untreated iron oxide (red pigment). Photographs and microscope images showing the dispersion state of SI-treated titanium (white pigment). Photographs and microscope images showing the dispersion state of untreated iron oxide (white pigment). Photographs and microscope images showing the dispersion state of SI-treated iron oxide (black pigment). Photographs and microscope images showing the dispersion state of untreated iron oxide (black pigment). Photographs and microscope images showing the dispersion state of SI-treated talc (extender pigment). Photographs and microscope images showing the dispersion state of carbon black.

[0017] Photographs and microscope images showing the dispersion state of titanium dioxide microparticles. A diagram showing the SPF measurement results of a dispersion of titanium dioxide microparticles. A diagram showing the color tone evaluation of iron oxide and carbon black in an organic solvent. Photographs showing the color tone evaluation of each pigment in an aqueous solvent and the dispersion state of Blue No. 1.

[0018] <Amide Alcohol> The amide alcohol used in the present invention is represented by the following formula (I): In the formula R １ is a C6 to C22 hydrocarbon group, R ２ is H or a C6 to C22 hydrocarbon group, R ３ is a linear or branched C2 to C21 hydrocarbon group.

[0019] In one embodiment of the present invention, １ is a C12 to C22 hydrocarbon group, and R ２ is H and R ３ In one embodiment of the present invention, amide alcohols of formula (I) in which R １ is a C12 to C22 unsaturated hydrocarbon group, and R ２ is H and R ３In another embodiment of the present invention, from the viewpoint of a low melting point, an amide alcohol of formula (I) in which R １ is a C12 to C22 branched chain hydrocarbon group, and R ２ is H and R ３ Amido alcohols of formula (I) wherein is a C3 to C8 hydrocarbon group are preferred.

[0020] In a preferred embodiment of the present invention, the amide alcohol of formula (I) is The compound is N-oleylhydroxyhexanamide having the structure:

[0021] <Pigment> In this specification, the term "pigment" refers to a powder that is insoluble or poorly soluble in water and oil, and includes color pigments used for coloring, extender pigments used for improving physical properties, pearl pigments, etc. The pigment used in the present invention is not particularly limited and can be appropriately selected depending on the desired application. For example, the pigment used in the present invention may be a fine powder that functions as an ultraviolet scattering agent.

[0022] Examples of pigments include, but are not limited to, the following: <Coloring pigments> Inorganic pigments: iron oxide (red iron oxide, yellow iron oxide, black iron oxide), carbon black, ultramarine, ferric iron oxide, chromium oxide, chromium hydroxide, manganese violet, titanium oxide, zinc oxide Organic pigments: red 2, blue 1, red 202, yellow 4, orange 201, green 201, red 201 <Pigments that function as ultraviolet absorbers and ultraviolet scattering agents> Inorganic pigments: finely divided titanium dioxide, finely divided zinc oxide, iron oxide, nickel oxide, manganese oxide, titanium phosphate, finely divided cerium oxide, cerium dioxide / calcium oxide complex, cerium phosphate, tin oxide, barium sulfate, barium oxide, magnesium oxide, aluminum oxide, tungstate, calcium tungstate, calcium phosphate, cobalt phosphate, calcium borate, zirconium oxide, silicon carbide, hydroxyapatite, hydrotalcite, talc, kaolin, diatomaceous earth, carbon black. Organic pigments: azo pigments, diazo pigments, bisazo pigments, phthalocyanine pigments, pigment yellow, pink. Pigment blue, Pigment red, fluorescein, benzotriazole pigments, cyanine pigments, amine pigments, naphthalene pigments, naphthalenesulfonic acid pigments, polyphenyl pigments, tetrahydrofuran pigments, sulfonic acid amino acid pigments, acrylamide pigments, anthraquinone pigments, ultramarine pigments, triphenylmethane pigments, aniline pigments, acetophenone pigments, allyl pigments, polymer pigments: polydimethylsiloxane, silicone pigments, polymethacrylate pigments, polyurethane pigments, epoxy pigments, polyvinyl alcohol, polyethylene pigments, polypropylene pigments

[0023] <Extender pigments> Inorganic pigments: mica, kaolin, talc, sericite, silicic acid, silicic anhydride, magnesium silicate, glass flake, synthetic phlogopite, clay, bentonite, bismuth oxychloride, synthetic fluorphlogopite, boron nitride, calcium carbonate, magnesium carbonate, aluminum silicate, alumina, alumina silica, zirconium oxide, magnesium oxide, aluminum oxide, barium sulfate, magnesium sulfate, zeolite, composite pigments of these, such as titanium oxide-coated mica, zinc oxide-coated mica, titanium oxide-zinc oxide-coated mica, iron oxide-coated mica, iron oxide-coated mica titanium, barium sulfate-titanium oxide-coated mica, iron oxide-coated synthetic phlogopite, chromium oxide-coated mica titanium, titanium oxide-coated glass powder, iron oxide-coated glass powder, titanium oxide-containing glass powder, iron oxide-containing glass powder Organic pigments: corn starch, silk powder, hemp cellulose powder, nylon, silicone, polyacrylic ester <Pearl pigments> Aluminum powder, bismuth oxychloride, red iron oxide-coated mica, iron oxide-coated mica titanium, titanium oxide / silicic anhydride composite-coated mica, glycol distearate, mica titanium, (PET / aluminum / epoxy resin) laminate, titanium oxide-coated borosilicate (Ca / Na), (PET / polymethyl methacrylate) laminate, modified acrylic resin. The pigment used in the present invention may be surface-treated with silicones such as methicone, dimethicone, and hydrogen dimethicone, amino acids, esters, metal soaps, etc.

[0024] <Pigment Dispersion Composition> The dispersant of the present invention can be used to disperse pigments in various compositions, such as cosmetic compositions, paint compositions, plastic compositions, etc. In one embodiment of the present invention, it is preferable to use the dispersant of the present invention in a composition containing an oil, particularly a cosmetic composition.

[0025] Cosmetics are materials that can be used in the manufacture of makeup products, body care products, skin care products, hair care products, fragrance products, etc., but are not limited to these. Makeup products include, but are not limited to, foundations such as liquid foundations, cream foundations, cushion foundations, and balm foundations, concealers, lip colors, lipsticks, lip balms, lip glosses, eyeliners, eyebrow products, mascara, eye shadows, blushers, highlighters, nail polishes, etc. Body care products include, but are not limited to, UV protection products, deodorant products, body skin care products, body fragrance products, and body cleansing products. Skin care products include, but are not limited to, cleansing products, facial cleansers, whitening cosmetics, UV protection cosmetics, and anti-aging products. Hair care products include, but are not limited to, hair sticks, hair styling waxes, hair treatments, one-day hair colorants, and hair glosses. Fragrance products include, but are not limited to, perfumes, eau de toilette, eau de cologne, eau de parfum, roll-on fragrances, stick-type solid perfumes, and the like.

[0026] In one embodiment of the present invention, the dispersant of the present invention is preferably used in a composition containing water and a water-soluble solvent such as a water-soluble organic solvent, or an oil-soluble solvent such as an oil-soluble organic solvent, particularly a paint composition. The paint composition is a material that can be used to manufacture, but is not limited to, writing instruments, painting supplies, paints for architectural applications, wax-containing laser printer toners, inkjet printer inks, etc. Examples of writing instrument products include, but are not limited to, capillary-type writing instruments such as water-based ballpoint pens and fountain pens, inks for oil-based ballpoint pens, pencils, mechanical pencil leads, colored pencils, markers, whiteboard pens, etc. Examples of painting supplies include, but are not limited to, watercolor paints, oil paints, acrylic paints, solid drawing materials, etc. In one embodiment of the present invention, the pigment dispersion composition is not an emulsion composition.

[0027] <Dispersion medium> The pigment dispersion composition of the present invention contains the dispersant of the present invention, a pigment, a solvent, and a dispersion medium, and the types of the pigment, solvent, and dispersion medium can be appropriately selected based on the desired application of the pigment dispersion composition. When the dispersant of the present invention is soluble in the dispersion medium, the pigment dispersion composition of the present invention does not need to contain a solvent.

[0028] In one embodiment of the present invention, when the pigment dispersion composition is a cosmetic composition, it is preferable to use an oil, a polyhydric alcohol, or an amphiphilic ester as the dispersion medium.

[0029] <Oil> The oil is not particularly limited as long as it is a component commonly used in cosmetics and the like. Examples include oils such as animal and vegetable oils, hydrocarbon oils, higher fatty acids, higher alcohols, ester oils, and silicone oils, and these can be used alone or in combination of two or more.

[0030] Examples of animal and vegetable fats and oils, or hydrogenated animal and vegetable fats and oils, include avocado oil, perilla oil, olive oil, cacao butter, kaya oil, apricot kernel oil, hardened oil, wheat germ oil, sesame oil, rice germ oil, rice bran oil, sugarcane wax, camellia oil, safflower oil, shea butter, Chinese ginger oil, cinnamon oil, soybean oil, tea seed oil, camellia oil, evening primrose oil, corn oil, rapeseed oil, germ oil, palm oil, palm kernel oil, castor oil, hardened castor oil, sunflower oil, grape oil, jojoba oil, macadamia nut oil, beeswax, cottonseed oil, cotton wax, Japan wax, montan wax, coconut oil, hardened coconut oil, peanut oil, lanolin, liquid lanolin, reduced lanolin, lanolin alcohol, hard lanolin, lanolin acetate, lanolin fatty acid isopropyl, and hexyl laurate.

[0031] Examples of hydrocarbon oils include dodecane, isododecane, ozokerite, squalane, squalene, ceresin, paraffin, isoparaffin, paraffin wax, liquid paraffin (mineral oil), pristane, polyisobutylene, polyisobutene, hydrogenated polyisobutene, microcrystalline wax, polyethylene wax, and petrolatum. Examples of higher fatty acids include lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, oleic acid, behenic acid, undecylenic acid, linoleic acid, linolenic acid, arachidonic acid, eicosapentaenoic acid (EPA), and docosahexaenoic acid (DHA). Examples of higher alcohols include hexyldecanol, isostearyl alcohol, octyldodecanol, myristyl alcohol, cetanol, stearyl alcohol, arachidyl alcohol, behenyl alcohol, and hydrogenated rapeseed oil alcohol.

[0032] Examples of ester oils include monoesters such as isononyl isononanoate and isotridecyl isononanoate, which are isononanoic acid esters; cetyl ethylhexanoate and hexyldecyl ethylhexanoate, which are 2-ethylhexanoic acid esters; isopropyl myristate, isocetyl myristate, and octyldodecyl myristate, which are myristate esters; ethyl isostearate, isopropyl isostearate, hexyldecyl isostearate, isostearyl isostearate, cholesteryl isostearate, and phytosteryl isostearate, which are isostearate esters; and milk oils. Examples of the oleic acid esters include isostearyl lactate and octyldodecyl lactate; oleic acid esters include oleyl oleate, phytosteryl oleate and octyldodecyl oleate; neopentanoic acid esters include isodecyl neopentanoate and isostearyl neopentanoate; palmitic acid esters include isopropyl palmitate and ethylhexyl palmitate; and others include ethylhexyl hydroxystearate, octyldodecyl neodecanoate, octyldodecyl ricinoleate, oleyl erucate, octyldodecyl erucate, and isopropyl lauroyl sarcosine.

[0033] Examples of diester oils include dipentaerythrityl hexaisononanoate, diisobutyl adipate, diisopropyl adipate, diethylhexyl succinate, neopentyl glycol diisononanoate, neopentyl glycol diethylhexanoate, neopentyl glycol dicaprate, diisostearyl malate, diisopropyl dilinoleate, ethylene glycol dioctanoate, octyldodecyl stearoyloxystearate, diisopropyl sebacate, di(cholesteryl / octyldodecyl) lauroyl glutamate, di(phytosteryl / octyldodecyl) lauroyl glutamate, etc. Examples of triester oils include triethylhexanoin, trimethylolpropane triethylhexanoate, caprylic / capric triglyceride, triisostearin, and trimethylolpropane triisostearate. Examples of tetraester oils include pentaerythrityl tetraethylhexanoate and pentaerythrityl tetraisostearate.

[0034] Examples of polyester oils include polyglycerin fatty acid esters such as polyglyceryl-2 isostearate, polyglyceryl-2 diisostearate, polyglyceryl-2 triisostearate, polyglyceryl-2 tetraisostearate, and polyglyceryl-2 dipolyhydroxystearate. Examples of high-viscosity ester oils include hydrogenated castor oil isostearate, hydrogenated castor oil dimer dilinoleate, (polyglyceryl-2 isostearate / dimer dilinoleate) copolymer, (phytosteryl / isostearyl / cetyl / stearyl / behenyl) dimer dilinoleate, dimer dilinoleyl bis(phytosteryl / behenyl / isostearyl) dimer dilinoleate, di(isostearyl / phytosteryl) dimer dilinoleate, hydrogenated dimer dilinoleyl rosin condensate, dimer dilinoleyl diisostearate, dimer dilinoleyl dimer dilinoleate, di(cholesteryl / behenyl / octyldodecyl) lauroyl glutamate, di(octyldodecyl / phytosteryl / behenyl) lauroyl glutamate, and myristoyl methylalanine (phytosteryl / decyltetradecyl).

[0035] Examples of silicone oils include dimethicone, dimethylpolysiloxane, methylphenylpolysiloxane, alkyl-modified organopolysiloxane, terminal-modified organopolysiloxane, fluorine-modified organopolysiloxane, amodimethicone, amino-modified organopolysiloxane, volatile silicone, alkyldimethicone, and cyclopentasiloxane.

[0036] <Polyhydric alcohols> Examples include pentylene glycol, 2-ethyl-1,3-hexanediol, 1,2-pentanediol, isopentyldiol, 1,3-butylene glycol, propane-1,2,3-triol, propane-1,2-diol, 1,2-heptanediol, 1,2-octanediol, 1,2-hexanediol, dipropylene glycol, and polypropylene glycol having an average molecular weight of 200 to 2000. <Amphiphilic esters> Examples include diethoxyethyl succinate, bisethoxydiglycol succinate, and bisethoxydiglycol cyclohexane-1,4-dicarboxylate.

[0037] In one embodiment of the present invention, when the pigment dispersion composition is an aqueous ink composition for a capillary-type writing instrument such as an aqueous ballpoint pen or a fountain pen, or a pigment dispersion composition for use therein, it is preferable to use water, a water-soluble organic solvent, or a mixture thereof as the dispersion medium. The water-soluble organic solvent is not particularly limited as long as it is a component commonly used in aqueous ballpoint pens, etc., and examples include hydroxyl group-containing water-soluble media such as ethylene glycol, diethylene glycol, propylene glycol, glycerin, propylene glycol monomethyl ether, and propylene glycol monomethyl ether acetate, and these can be used alone or in combination of two or more.

[0038] In one embodiment of the present invention, when the pigment dispersion composition is an oil-based ink composition for an oil-based ballpoint pen or the like, or a pigment dispersion composition for use therein, it is preferable to use an oil-soluble organic solvent as the dispersion medium. The oil-soluble organic solvent is not particularly limited as long as it is a component commonly used in oil-based ballpoint pens, etc., but examples include ethylene glycol monophenyl ether, benzyl alcohol, propylene glycol, dipropylene glycol, 1,3-butylene glycol, hexylene glycol, tetralin, propylene glycol monophenyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monomethyl ether acetate, tripropylene glycol monomethyl ether, N-methyl-2-pyrrolidone, etc., and these can be used alone or in combination of two or more.

[0039] In one embodiment of the present invention, when the pigment dispersion composition is an aqueous paint composition, it is preferable to use water, a water-soluble organic solvent, or a mixture thereof as the dispersion medium. The water-soluble organic solvent is not particularly limited as long as it is a component commonly used in aqueous paints, etc., but examples include hydroxyl group-containing water-soluble media such as alcohols, diols, and glycerin, and these can be used alone or in combination of two or more.

[0040] In one embodiment of the present invention, when the pigment dispersion composition is an oil paint composition, it is preferable to use an oil-based medium based on a drying oil as the dispersion medium. The drying oil is not particularly limited as long as it is a component commonly used in oil paints, but examples thereof include linseed oil, poppy oil, walnut oil, safflower oil, stand oil (heat-polymerized linseed oil), and turpentine oil (refined turpentine oil).

[0041] In one embodiment of the present invention, when the pigment dispersion composition is a solid drawing material composition such as a crayon, it is preferable to use an oil such as a wax (e.g., polyethylene), a solid oil, or a liquid oil as the dispersion medium. The wax may be any component commonly used in solid drawing materials, including petroleum waxes (e.g., microcrystalline wax and paraffin wax), synthetic waxes (e.g., polyethylene wax), and vegetable or animal waxes (e.g., carnauba wax, Japan wax, beeswax, and rice wax). The solid oil may be any component commonly used in solid drawing materials, including hardened palm kernel oil, petrolatum, coconut oil, cocoa butter, shea butter, mango butter, and avocado butter. The liquid oil may be any component commonly used in solid drawing materials, including animal oil, vegetable oil, mineral oil, silicone oil, and ester oil.

[0042] In one embodiment of the present invention, when the pigment dispersion composition is a paint composition for coating buildings or the like, the dispersion medium can be appropriately selected depending on the type of composition. In the case of water-based paints, in addition to water, polyhydric alcohols such as glycerin, ethylene glycol, 1,3-butylene glycol, and dipropylene glycol can be used. On the other hand, in the case of solvent-based or oil-based paints, organic solvents such as xylene, toluene, butyl acetate, isobutyl alcohol, mineral spirits, methyl isobutyl ketone, cyclohexanone, n-butanol, isopropanol, paraffinic hydrocarbons, and naphtha can be used.

[0043] In one embodiment of the present invention, when the pigment dispersion composition is a wax-containing toner composition for laser printers, wax, an organic solvent, a polyhydric alcohol, or the like is used as a dispersion medium. The wax may be any component used in conventional toners, including polyethylene wax, polypropylene wax, carnauba wax, beeswax, paraffin wax, and olefin-based wax. The organic solvent may be any component used in conventional toners, including toluene, xylene, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, n-butanol, isopropanol, propylene glycol monomethyl ether, butyl acetate, naphtha, and / or paraffin-based hydrocarbons. The polyhydric alcohol may be any component used in conventional toners, including glycerin, ethylene glycol, 1,3-butylene glycol, and dipropylene glycol.

[0044] In one embodiment of the present invention, when the pigment dispersion composition is an ink composition for inkjet printers, it is preferable to use water, a lower alcohol, or an organic solvent as the dispersion medium. The lower alcohol is not particularly limited as long as it is a component commonly used in inkjet printer inks, and examples thereof include methanol, ethanol, n-propanol, i-propanol, n-butanol, i-butanol, sec-butanol, and tert-butanol.The organic solvent is not particularly limited as long as it is a component commonly used in inkjet printer inks, and examples thereof include polyhydric alcohols such as ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, propylene glycol, 1,3-butanediol, 1,3-propanediol, 2-methyl-1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, glycerin, 1,2,6-hexanetriol, 2-ethyl-1,3-hexanediol, 1,2,4-butanetriol, 1,2,3-butanetriol, and petriol; ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol monobutyl ether, tetraethylene glycol polyhydric alcohol alkyl ethers such as glycol monomethyl ether and propylene glycol monoethyl ether; polyhydric alcohol aryl ethers such as ethylene glycol monophenyl ether and ethylene glycol monobenzyl ether; nitrogen-containing heterocyclic compounds such as N-methyl-2-pyrrolidone, N-hydroxyethyl-2-pyrrolidone, 2-pyrrolidone, 1,3-dimethylimidazolidinone and ε-caprolactam; amides such as formamide, N-methylformamide and N,N-dimethylformamide; amines such as monoethanolamine, diethanolamine, triethanolamine, monoethylamine, diethylamine and triethylamine; sulfur-containing compounds such as dimethyl sulfoxide, sulfolane and thiodiethanol; propylene carbonate, ethylene carbonate, γ-butyrolactone, methyl ethyl ketone, isopropyl alcohol; ethyl acetate, butyl acetate, naphtha and paraffin hydrocarbons.

[0045] <Solvent> The amide alcohol of the present invention is solid at room temperature, so it is preferable to dissolve it in advance. The solvent is not particularly limited as long as it can dissolve the amide alcohol, but a solvent that can maintain the amide alcohol in a dissolved state at room temperature after dissolution is preferred, such as a liquid oil. In one embodiment of the present invention, a higher alcohol that is liquid at room temperature is preferably used as the solvent for the amide alcohol of the present invention. In a preferred embodiment of the present invention, hexyldecanol, isostearyl alcohol, and / or octyldodecanol is preferably used as the solvent for the amide alcohol of the present invention. In one embodiment of the present invention, when the dispersion medium is an oil, an oil, a polyhydric alcohol, or an amphiphilic ester, a higher alcohol that is liquid at room temperature, such as hexyldecanol, isostearyl alcohol, or octyldodecanol, is preferably used as the solvent for the amide alcohol of the present invention.

[0046] In another embodiment of the present invention, when the dispersion medium contains a wax, higher alcohols that are liquid at room temperature, toluene, xylene, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, n-butanol, isopropanol, propylene glycol monomethyl ether, butyl acetate, naphtha, and / or paraffinic hydrocarbons may be used as the solvent.

[0047] <Other Ingredients> The cosmetic composition of the present invention may contain any ingredient commonly used in cosmetics. Examples of these additional ingredients include water; UV absorbers such as ethylhexyl methoxycinnamate, diethylaminohydroxybenzoyl hexyl benzoate, and octocrylene; quality-preserving ingredients such as antioxidants and preservatives; medicinal ingredients and active ingredients such as whitening agents, anti-wrinkle agents, and antioxidants; fragrances; water-soluble or oil-soluble dyes; surfactants such as PEG-30 glyceryl triisostearate and PEG-8 diisostearate; waxes such as candelilla wax, microcrystalline wax, beeswax, polyethylene wax, and ceresin; and thickeners such as dextrin palmitate. These can be combined as appropriate.

[0048] The coating composition of the present invention may contain any component generally used in coatings. Examples of additional components in ink compositions for writing instruments include pigments and dyes that can be used in combination as colorants. The dyes are not particularly limited as long as they are dyes that have been conventionally used in ballpoint pen ink compositions, and examples thereof include Rhodamine B base (C.I. 45170B), Soldan Red 3R (C.I. 21260), Methyl Violet 2B base (C.I. 42535B), Victoria Blue F4R (C.I. 42653B), Nigrosine base LK (C.I. 50415), and Valifath Yellow #3104 (C.I. 1), an oil-based dye manufactured by Orient Chemical Industry Co., Ltd. 3900A), Balifast Yellow #3105 (C.I. 18690), Orient Spirit Black AB (C.I. 50415), Balifast Black #3804 (C.I. 12195), Balifast Yellow #1109, Balifast Orange #2210, Balifast Red #1320, Balifast Blue #1605, Balifast Violet #1701, and oil-based dyes manufactured by Hodogaya Chemical Co., Ltd., such as Spiron Black GMHC Special, Spiron Yellow C-2GH, Spiron Red C-GH, Spiron Red C-BH, Spiron Blue BPNH, Spiron Blue C-RH, Spiron Violet C-RH, S.P.T. Orange 6, and S.P.T. Blue-111.

[0049] Another example of an additional component in a writing instrument ink composition is a resin component that may be added for purposes such as increasing viscosity, improving handwriting fixation, or further improving the dispersion stability of the pigment. The resin component is not particularly limited as long as it is a resin component conventionally used for such purposes, and examples include ketone resins, xylene resins, polyethylene oxide, rosin resins, rosin derivatives, terpene resins, coumarone-indene resins, polyvinyl butyral, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymers, polymethacrylate esters, polyacrylic acid-polymethacrylic acid copolymers, polyacrylic acid, styrene-maleic acid resins, and styrene-acrylic resins. Further additional components in a writing instrument ink composition include surfactants such as anionic, nonionic, and cationic surfactants, other resins, adhesives, rust inhibitors, lubricants, and preservatives. These can be combined as appropriate.

[0050] In the aqueous paint composition, as an additional component, a dye can be used in addition to a pigment as a coloring material. Other examples of additional ingredients in aqueous paint compositions include water-soluble preservatives and mildewcides for inhibiting decay and mildew growth (e.g., chloroacetamide, 2-pyridinethiol-1-oxide sodium salt, sodium dehydroacetate, sodium benzoate, sodium sorbate, potassium sorbate, 2-bromo-2-nitropropane-1,3-diol, 3-iodo-2-propynyl butylcarbamate, 1,2-benzisothiazolin-3-one, 5-chloro-2-methyl-4-isothiazolin-3-one, 2-methyl-4-isothiazolin-3-one thiabendazole, phenoxyethanol, sodium fluoride, 4-(2-nitrobutyl)morpholine, 1,3-dimorpholino-2-ethyl-2-nitripropane); defoamers, antifoaming agents, surfactants, and additional pigment dispersants.

[0051] As additional components in the oil paint composition, pigment dispersants and thickeners other than the dispersant of the present invention can be used to aid in dispersing the pigment, and examples of these include aluminum stearate, lecithin, bentonite, hydroxypropyl cellulose, carboxymethyl cellulose, polyurethane acrylate, acrylic acid ester polymers, silica, etc. Other examples of additional components in oil paint compositions include antioxidants (e.g., dibutylhydroxytoluene, tocopherol, ascorbic acid, propyl gallate) for improving the storage stability and drying acceleration of oil paints; drying accelerators (e.g., metal salts such as valtone naphthenate, manganese naphthenate, zirconium octanoate, calcium octanoate, iron(III) naphthenate, lithium naphthenate, etc.) for accelerating drying; preservatives and mildew inhibitors (e.g., phenoxyethanol, sodium sorbate, potassium sorbate, sodium dehydroacetate, chloroacetamide, 2-pyridinethiol-1-oxide sodium salt, 1,2-benzisothiazolin-3-one 5-chloro-2-methyl-4-isothiazolin-3-one dithiazine) for preventing spoilage and mold growth during storage; and defoamers, antifoaming agents, surfactants, etc. for preventing foam generation during the manufacturing process.

[0052] Additional components in paint compositions for painting buildings and the like include, from the viewpoint of preservation, antiseptic and antifungal components (e.g., phenoxyethanol, chloroacetamide, 1,2-benzisothiazolin-3-one, 5-chloro-2-methyl-4-isothiazolin-3-one, 2-methyl-4-isothiazolin-3-one, 2-bromo-2-nitropropane-1,3-diol, 3-iodo-2-propynyl butylcarbamate, thiabendazole, sodium fluoride); defoamers and antifoaming agents (e.g., dimethicone, methyl methyl fluoride) for suppressing bubbles generated during pigment dispersion and the painting process; dispersants for improving the dispersion stability of the pigment (for example, acrylic acid-methacrylic acid copolymer, polyether-modified polyurethane, polyesteramide, polycarboxylic acid resin); binder resins for imparting adhesion, flexibility, weather resistance, water resistance, etc. to the coating film (for example, acrylic, urethane, alkyd, silicone-modified resin, fluorine-based resin, epoxy resin); surfactants, ultraviolet absorbers, viscosity modifiers, drying accelerators.

[0053] Additional components in a toner composition containing wax include antioxidants, moisture-proofing agents, and preservative components (e.g., butylhydroxytoluene, butylhydroxyanisole, tris(2,4-di-tert-butylphenyl)phosphite, phenolic antioxidants, and propylene glycol); defoamers and antifoaming agents (e.g., dimethyl silicone, polydimethylsiloxane, polyoxyethylene-polyoxypropylene copolymers, fatty acid derivatives, and mineral oils); auxiliary dispersants (e.g., acrylic acid-methacrylic acid copolymers, polyether-modified polyurethanes, polyester amides, polycarboxylic acid resins, and styrene-maleic acid copolymers); binder resins for forming the structure of toner particles and ensuring performance (e.g., styrene-acrylic resins, polyester resins, polyurethane resins, epoxy resins, and phenolic resins); charge control agents (e.g., nigrosine derivatives, metal complex compounds, and organic sulfonates); external additives (e.g., silica and titanium oxide); surfactants; viscosity modifiers; and resin stabilizers.

[0054] Additional components in the inkjet printer composition include polymer compounds such as polyurethane-based dispersants (e.g., polyurethane diol), acrylic acid-based dispersants (e.g., acrylic acid methacrylic acid copolymer), polyester-based dispersants (e.g., polyethylene glycol), polycarboxylic acid-based dispersants (e.g., sodium polyacrylate), and epoxy-based dispersants (e.g., epoxy resin) for improving the fluidity of the ink and the dispersion stability of the pigment; and binder resins (e.g., polyurethane-based resins such as styrene-acrylic acid copolymer and polyurethane diol, polyester-based resins such as polyethylene terephthalate, epoxy resins, and phenolic resins) for improving the fixation and water resistance of the ink.

[0055] The present invention also provides a pigment dispersion composition comprising: (A) an amide alcohol of formula (I), (B) a solvent, (C) a dispersing medium, (D) a pigment, and optionally (E) other ingredients. The present invention also provides a pigment dispersion composition comprising: an amide alcohol dispersing medium of formula (I), a pigment, and optionally other ingredients. The pigment dispersion composition may be any of a variety of compositions, such as the above-mentioned cosmetic composition, coating composition, or plastic composition.

[0056] The content of each component in such a pigment dispersion composition is not particularly limited and can be appropriately selected depending on the intended use of the composition, the type of pigment, etc. In one embodiment of the present invention, the content of the amide alcohol of formula (I) in the pigment dispersion composition is, for example, 0.01 to 6 wt%, preferably 0.01 to less than 3 wt%, more preferably 0.1 to 2 wt%, and even more preferably 0.3 to 1 wt%. In another embodiment of the present invention, the content of the amide alcohol of formula (I) in the pigment dispersion composition is, for example, 0.1 to 5 wt%, preferably 0.1 to 3 wt%, and more preferably 0.3 to 1 wt%.

[0057] In yet another embodiment of the present invention, the content of the amido alcohol of formula (I) in the pigment dispersion composition is, for example, 0.01 to 6% by weight, preferably 0.1 to 5% by weight, and more preferably 1 to 4% by weight.

[0058] The ratio of the amide alcohol of formula (I) to the pigment in the pigment dispersion composition can also be selected appropriately depending on the intended use of the composition, the type of pigment, etc. In one embodiment of the present invention, the weight ratio of the amide alcohol of formula (I) to the pigment is, for example, 1:1 to 1:30, preferably 1:3 to 1:30, more preferably 1:5 to 1:30, and even more preferably 1:10 to 1:30. In another embodiment of the present invention, for example, in an emulsion composition such as a foundation, the weight ratio of the amide alcohol of formula (I) to the pigment is, for example, 1:3 to 1:30, preferably 1:7 to 1:30, more preferably 1:10 to 1:30, and even more preferably 1:15 to 1:30.

[0059] In yet another embodiment of the present invention, the weight ratio of the amide alcohol of formula (I) to the pigment is, for example, from 1:0.01 to 1:20, preferably from 1:0.1 to 1:15, and more preferably from 1:0.5 to 1:10.

[0060] While JP 2019-85544 A and the like teach combining an amide alcohol with a carboxyl group-containing polymer for emulsifying an emulsion composition, the carboxyl group-containing polymer is not necessary to obtain the pigment dispersion effect of the present invention, and therefore the pigment dispersion composition of the present invention may or may not contain a carboxyl group-containing polymer. In one aspect of the present invention, the pigment dispersion composition is free of a carboxyl group-containing polymer or contains less than 3 wt% of a carboxyl group-containing polymer. In another aspect of the present invention, when the pigment dispersion composition contains a carboxyl group-containing polymer, it is free of one or more polyglycerol fatty acid esters having hydroxyl groups or contains less than 3 wt% of a carboxyl group-containing polymer.

[0061] <Method for Dispersing Pigment> In one aspect of the present invention, a method for dispersing a pigment in a dispersion medium using an amide alcohol of formula (I) of the present invention is provided. Because the amide alcohol of formula (I) of the present invention is solid at room temperature, it is preferable to dissolve it in a solvent beforehand. Therefore, in a preferred aspect of the present invention, the method for dispersing a pigment includes: (1) dissolving the amide alcohol of formula (I) in a solvent to obtain a mixture; and (2) mixing the pigment together with the mixture obtained in step (1) with a dispersion medium to disperse the pigment. The mixing method can be appropriately selected depending on the type of dispersion medium, etc. In step (1), the amide alcohol of formula (I) and the solvent can be heated together to dissolve the mixture, or each can be heated separately to dissolve the mixture. In step (2), the mixing method can be appropriately selected depending on the type of dispersion medium, etc.

[0062] The solvent used in the present invention is not particularly limited as long as it can dissolve the amide alcohol, but a solvent that can dissolve the amide alcohol at room temperature is preferred, and examples thereof include liquid oils. In one embodiment of the present invention, it is preferred to use a higher alcohol that is liquid at room temperature as the solvent for the amide alcohol of formula (I) of the present invention. In a preferred embodiment of the present invention, it is preferred to use hexyldecanol, isostearyl alcohol, and / or octyldodecanol as the solvent for the amide alcohol of formula (I) of the present invention.

[0063] In addition, when the main dispersion medium in the pigment dispersion composition is a medium in which the amide alcohol of formula (I) is soluble, such as a lower alcohol such as ethanol, an alcohol that is liquid at room temperature, such as a polyhydric alcohol such as pentylene glycol, or an organic solvent such as acetone, from the viewpoint of simplifying the process, the pigment may be directly mixed with the amide alcohol of formula (I) and the dispersion medium without using step (1).

[0064] <Method for Producing a Pigment Dispersion Composition> In one aspect of the present invention, a method for producing a pigment dispersion composition using an amide alcohol of formula (I) of the present invention is provided. Because the amide alcohol of formula (I) of the present invention is solid at room temperature, it is preferably dissolved in a solvent in advance and mixed with the pigment. Therefore, in a preferred aspect of the present invention, the method for producing a pigment dispersion composition includes: (1) dissolving the amide alcohol of formula (I) in a solvent to obtain a mixture; and (2) mixing and dispersing the pigment together with the mixture obtained in step (1) with a dispersion medium and any other components. In step (1), the amide alcohol of formula (I) and the solvent may be heated together to dissolve the mixture, or each may be heated separately to dissolve the mixture. In step (2), the mixing method can be appropriately selected depending on the composition and application of the pigment dispersion composition.

[0065] In addition, when the main dispersion medium in the pigment dispersion composition is a medium in which the amide alcohol of formula (I) is soluble, such as a lower alcohol such as ethanol, an alcohol that is liquid at room temperature, such as a polyhydric alcohol such as pentylene glycol, or an organic solvent such as acetone, from the viewpoint of simplifying the process, the amide alcohol of formula (I) may be directly mixed with the dispersion medium without using step (1).

[0066] In one aspect, the present invention provides a pigment dispersion composition obtained by the above-mentioned method. The solvent, dispersion medium, and other components used in the method are as described above. In one aspect of the present invention, the pigment dispersion composition is preferably the above-mentioned cosmetic composition.

[0067] In one embodiment of the present invention, the pigment dispersion composition is a UV care cosmetic composition containing a fine powder that functions as an ultraviolet scattering agent as a pigment. In another embodiment of the present invention, the pigment dispersion composition is a paint composition, a toner composition, or a coating paint containing multiple types of pigments, for example, a color pigment and an extender pigment, as pigments.

[0068] The use of an amido alcohol of formula (I) in a writing instrument composition provides at least one of the following advantages: Improved dispersibility improves the ink's blackness, allowing for the development of thicker, clearer lines. Highly dispersible inks have uniformly dispersed particles, allowing for smooth flow from the pen tip to the paper. This results in a very smooth writing experience, enabling comfortable writing without any snagging. Good ink dispersion facilitates stable line thickness and color development during writing. Uniform particle distribution across the paper surface reduces color unevenness, resulting in consistently consistent handwriting. The risk of ink clogging is also reduced. Evenly dispersed particles reduce the likelihood of ink solidifying inside the pen or at the pen tip, ensuring stable writing, especially with fine-point pens or when not used for extended periods of time. Improved dispersibility also contributes to the ink's quicker drying. Evenly spreading ink across the paper accelerates drying, reducing the risk of hand smearing written characters. - Highly dispersible inks are resistant to long-term storage and temperature changes, and are less likely to separate or deteriorate. This is a major advantage in terms of maintaining the quality and reliability of writing instruments.

[0069] The use of an amide alcohol of formula (I) in an aqueous paint composition provides at least one of the following advantages: Fine, uniform dispersion of the pigment stabilizes light reflection and absorption, improving color development and making colors appear more vivid and bright. It also reduces color unevenness when applied, resulting in a more uniform and beautiful finish. Improved dispersibility also contributes to shelf life; by reducing pigment sedimentation, the components tend to remain stable without separation even during long-term storage. The fluidity of the paint improves when applied with a brush or paintbrush, allowing for smooth application and improving workability. After drying, the pigment is uniformly fixed to the binder, improving the adhesion and durability of the paint film. Efficient color development reduces the amount of pigment needed to achieve the same color, resulting in cost savings. For these reasons, pigment dispersibility in aqueous paints is an important factor that significantly affects their quality and ease of use.

[0070] The use of an amido alcohol of formula (I) in an oil paint composition provides at least one of the following advantages: Improved pigment dispersibility improves the color development of the oil paint. Uniform pigment dispersion improves the vividness and uniformity of the color obtained after application of the paint, reducing color unevenness. This allows for more accurate and vivid color expression. This effect is particularly noticeable when fine color adjustment is required. Improved pigment dispersibility improves the paint's application. Uniform pigment dispersion allows the oil paint to be applied more smoothly, resulting in smoother and more consistent brushstrokes. This reduces uneven application and pressure marks, reducing the effort and time required for creating artwork. It also allows for more precise application of fine details. Improved pigment dispersibility also contributes to improved drying of the oil paint. Uniform pigment dispersion results in an even coating of the oil paint as it dries, resulting in a more consistent drying time and more consistent coating hardening. This makes the time it takes to complete a painting more predictable and provides a stable working environment. Improved pigment dispersion prevents pigment settling and separation. Evenly dispersed pigments prevent pigment settling and maintain a uniform state even when stored for long periods. This reduces the need for remixing before storage or use, saving labor and ensuring the quality of the oil paint remains stable over time. Improved pigment dispersion also improves the paint's weather resistance and durability. Uniformly dispersed pigments work evenly within the paint film and are more resistant to external factors such as UV rays and temperature changes. This ensures that the colors of the painting remain vibrant and fade-resistant over time. Improved pigment dispersion also leads to increased efficiency in the manufacturing process. Properly dispersed pigments reduce the need for additional dispersion and mixing steps during paint production, reducing manufacturing costs. Furthermore, a smoother manufacturing process maintains consistently high product quality.

[0071] The use of an amide alcohol of formula (I) in a paint composition for application to buildings and the like provides at least one of the following advantages: Uniform dispersion of the pigment stabilizes light reflection and absorption, improves color development, and makes the painted surface appear vivid and bright. This results in a beautiful exterior appearance for the painted building, and the vividness of the color can be maintained for a long period of time. Improved pigment dispersibility reduces color unevenness during application, resulting in a uniform and beautiful finish. Furthermore, uniform pigment dispersion improves the fluidity of the paint, making application smoother and significantly improving workability. High pigment dispersibility also has a positive effect on the shelf life of the paint. Stable dispersion of the pigment by the dispersant suppresses pigment precipitation, allowing the paint to remain stable without separation even during long-term storage. This preserves the quality of the paint, and maintains high quality even when reused. Improved pigment dispersibility also has a positive effect on the performance of the paint after drying. By dispersing the pigments evenly and firmly fixing them to the binder, the adhesion and durability of the coating film are improved, and peeling and fading of the coating film are prevented.

[0072] The use of an amido alcohol of formula (I) in a wax-containing toner composition for a laser printer provides at least one of the following advantages: Uniform dispersion of the pigment improves the color reproducibility of the printed toner. Proper dispersion of the pigment shortens the drying time of the ink or toner and optimizes the viscosity of the toner, achieving uniform application during printing. This prevents color unevenness and uneven color development during printing, making it possible to obtain clear images. Improved pigment dispersibility also improves the storage stability of the toner. Stable dispersion of the pigment by the dispersant suppresses pigment precipitation and prevents pigment separation and aggregation even during long-term storage. This maintains the quality of the toner and ensures stable printing performance even after long-term use. Uniform dispersion of the wax molecules and pigment improves the fluidity of the toner, allowing it to be applied smoothly to the printed surface. This improves toner adhesion and improves the durability and wear resistance of printed materials.

[0073] The use of an amido alcohol of formula (I) in an ink composition for an inkjet printer provides at least one of the following advantages: Uniform dispersion of the pigment improves the color reproducibility of the ink produced by the inkjet printer. Appropriate dispersion of the pigment shortens the drying time of the ink, achieving uniform application during printing with an inkjet printer. This prevents uneven color and non-uniform color development during printing with an inkjet printer, making it possible to obtain clear images. Improved pigment dispersibility also improves the storage stability of the ink. Stable dispersion of the pigment by the dispersant suppresses pigment precipitation and prevents pigment separation and aggregation even during long-term storage. This maintains the quality of the ink even over long periods of use, ensuring stable printing performance. Uniform dispersion of pigment molecules improves the fluidity of the ink, allowing it to be smoothly supplied to the ink head of the inkjet printer. This results in uniform ink jetting, improving the durability and color development of printed products.

[0074] The present invention will be described in more detail below based on examples, but the present invention is not limited to these examples and various modifications are possible within the scope of the technical concept of the present invention. In this specification, % means % by weight unless otherwise specified.

[0075] [Test Example 1] [Sample Preparation Method] (1) Various dispersants were dissolved in hexyldecanol (product name: Lisonol 16SP, supplier: Kokyu Alcohol Kogyo Co., Ltd.) at a concentration of 3 wt. %. OLH was heated in a 90°C thermostatic bath, and oleic acid monoamide and cocamide MEA were heated in an 80°C thermostatic bath depending on their melting points. (2) The 3 wt. % dispersant-containing mixture prepared in (1) was mixed with each oil at a weight ratio of 1:2 to prepare a dispersion medium. The dispersant concentration relative to the total dispersion medium was 1 wt. %. For the comparative example without added dispersant, hexyldecanol and various oils were mixed at a weight ratio of 1:2. (3) 4.5 g of the dispersion medium prepared in (2) and 0.5 g of pigment were weighed into a colorimetric tube and heated in an 80°C thermostatic bath for 10 minutes. (4) The mixture was dispersed in a vortex mixer for 1 minute to obtain a slurry.

[0076] Details of the components used are shown below. <Dispersant>

[0077] chemical structure

[0078] In the chemical structure of Cocamide MEA, R is derived from coconut oil fatty acid, which is a mixture of saturated and unsaturated fatty acids such as lauric acid, which has 12 carbon atoms, and myristic acid, which has 14 carbon atoms, and is composed mainly of C11 to C13 straight-chain hydrocarbon groups. In this specification and drawings, N-oleylhydroxyhexanamide, which is the amide alcohol of formula (I) of the present invention, will be referred to as "OLH," oleic acid monoamide, which is a dispersant in a comparative example, will be referred to as "E-10," and Cocamide MEA will be referred to as "MEA."

[0079] <Dispersion medium: oil>

[0080] <Pigments>

[0081] [Evaluation] Color Difference Evaluation [1] Color Measurement Measurement was performed using a spectrophotometer SE7700 (Nippon Denshoku Industries Co., Ltd.) using the following procedure. (1) A color comparison tube was placed in the measurement section (reflection measurement) of the color difference meter. (2) The color comparison tube was covered with a cylindrical piece of black construction paper. (3) The color (lightness L) was measured at five points (left, right, top, bottom, and center) on the bottom of the color comparison tube. ＊ , chromaticity a ＊ b ＊ , saturation c ＊ ) (4) The average of the five points is the measurement value.

[0082] [2] Evaluation of color tone The color (lightness L ＊ , chromaticity a ＊ b ＊ The results of the change in color tone due to the addition of a dispersant for each of the above-mentioned pigments are shown in Figures 1 to 9. ＊ and characteristic color tone were evaluated. ＊ = {(ΔL ＊ ) ２ + (Δa ＊ ) ２ + (Δb ＊ ) ２} １／２ ΔE ＊ ΔE = 0.8 to 1.6: A slight color difference is noticeable when comparing adjacent images ＊ ΔE = 1.6 to 3.2: A level that is barely noticeable when comparing from a distance and is generally considered to be the same color ＊ = 3.2 to 6.5: A range that can be treated as the same color at the impression level. Yellow pigments that are sometimes the subject of complaints in the paint industry: Chromaticity b ＊ (Yellow 60 ⇔ -60 Blue) is measured and the yellowness is evaluated. The closer the value is to 60, the better. Red pigment: Chromaticity a ＊ (Red 60 ⇔ -60 Green) is measured and the redness is evaluated. The closer the value is to 60, the better. White pigment: Lightness L ＊ (white 100 ⇔ 0 black) and chromaticity b ＊ (Yellow 60 ⇔ -60 Blue) was measured to evaluate whiteness and yellowing. ＊ The closer the value is to 100, the better. ＊ The closer the value is to 0, the better. Black pigment: Lightness L ＊The blackness was evaluated by measuring the value (white 100 ⇔ black 0). The closer the value is to 0, the better. Note that since talc is an extender pigment, color tone was not evaluated.

[0083] Evaluation of dispersion stability The state of the slurry was observed visually and under a microscope the day after slurry preparation. In addition, the automatic area measurement function of a digital microscope VHX8000 (Keyence Corporation) was used to calculate the percentage of aggregated particles in the entire microscope image. The results are shown in Figures 10 to 19. The number in the upper right corner of the microscope image is the percentage of aggregates.

[0084] [Summary of Color Improvement Effect] The overall evaluation of the results obtained using the color difference meter is shown in Table A. ◯ means that the color improvement effect is very good, △ means that the color improvement effect is good, and × means that the color improvement effect is poor. More specifically, the difference x between the best chromaticity and the worst chromaticity among the additive-free and three additives was calculated, and the overall evaluation was carried out by rating ◯ for chromaticity that was in the range of [best chromaticity] to [that chromaticity - x / 3], △ for chromaticity that was in the range of [that chromaticity - x / 3] to [that chromaticity - 2x / 3], and × for chromaticity that was in the range of [that chromaticity - 2x / 3] to [worst chromaticity].

[0085]

[0086] From the above results, it can be seen that the amide alcohol of the present invention has the same color improvement effect as the conventional product MEA. In particular, it can be seen that the color improvement effect of SI-treated (hydrogen dimethicone-treated) pigments is particularly high.

[0087] [Summary of Dispersion Stability] The overall evaluation of dispersion stability by visual observation is shown in Table B. ◯ means that there is almost no particle settling and the dispersion stability is very excellent, △ means that there is little particle settling and the dispersion stability is excellent, and × means that all particles have settled and the dispersion stability is poor.

[0088]

[0089] The overall evaluation of the inhibition of aggregate formation as determined by microscope observation is shown in Table C. ◯ means very excellent inhibition of aggregate formation, △ means excellent inhibition of aggregate formation, and × means poor inhibition of aggregate formation. More specifically, the difference x between the aggregation rate with the least particle aggregation and the highest aggregation rate among the additive-free and three additives was determined, and the overall evaluation was performed by rating ◯ for a sample that showed a chromaticity within the range of [lowest aggregation rate] to [that rate - x / 3], △ for a sample that showed a chromaticity within the range of [that rate - x / 3] to [that rate - 2x / 3], and × for a sample that showed a chromaticity within the range of [that rate - 2x / 3] to [highest aggregation rate].

[0090] From the above results, it can be understood that the amido alcohol of formula (I) of the present invention exhibits good dispersion stability in various dispersions.

[0091] Test Example 2 Fine Powder Dispersion Composition Functioning as an Ultraviolet Scattering Agent Sample Preparation Method Using fine particle titanium oxide as the pigment, a slurry was prepared using the same ingredients and preparation method as in Test Example 1.

[0092] <Pigments>

[0093] [Evaluation] Evaluation of dispersion stability The state of the slurry was observed visually and under a microscope the day after the slurry preparation. The results are shown in Figure 20. From the appearance observation of the dispersion, it was found that the incorporation of the amide alcohol of the present invention's formula (I) suppressed particle sedimentation. From the microscope observation, it was found that it contributed to the uniform dispersion of titanium dioxide fine particles.

[0094] SPF measurement: 0.0385 g of the slurry was evenly applied to a PMMA resin plate, and after leaving it to stand in a cool, dark place for 15 minutes, the SPF value was measured using an SPF analyzer UV-2000S. The increase in SPF value is thought to be due to the dispersion stability of the amide alcohol of formula (I) of the present invention.

[0095] Test Example 3 Pigment Dispersion Composition for Oil-Based Ink Sample Preparation Method (1) The raw materials were weighed into a No. 5 screw tube and heated in a thermostatic bath at 80°C. (2) The mixture was dispersed in a vortex mixer for 1 minute to obtain a dispersion.

[0096] The formulation is shown below.

[0097] <Pigments>

[0098] <Dispersion medium> Ethanol, benzyl alcohol, acetone, and toluene were used. <Dispersant> The same dispersant as in Test Example 1 was used.

[0099] [Evaluation] As in Color Difference Evaluation Test Example 1, lightness L ＊ The blackness was evaluated by measuring (white 100 ⇔ black 0).

[0100] Test Example 4 Pigment Dispersion Composition for Water-Based Ink Sample Preparation Method (1) The raw materials were weighed into a No. 5 screw tube and heated in a thermostatic chamber at 80°C. (2) The mixture was dispersed in a vortex mixer for 1 minute to obtain a dispersion.

[0101] The formulation is shown below.

[0102] <Pigments>

[0103] <Dispersant> The same dispersant as in Test Example 1 was used.

[0104] [Evaluation] Color was measured in the same manner as in Color Difference Evaluation Test Example 1. Black pigment (iron oxide, carbon black): Lightness L ＊ (White 100 ⇔ 0 black) was measured and the blackness was evaluated. Blue pigment: Chroma c ＊ was measured to evaluate the vividness.

[0105] Evaluation of Dispersion Stability: For the blue pigments for which the improvement in color difference was slight, the state of the dispersions was visually observed the day after preparation. The results are shown in Figure 24. It can be seen that for all pigments, the addition of the amide alcohol of Formula (I) of the present invention to an aqueous dispersion medium (a solution of ethanol and water mixed at a weight ratio of 4:1) results in an improvement in color tone. Furthermore, the color development improvement effect was evaluated in terms of saturation, and a slight improvement was found, but visual evaluation of the dispersions confirmed that the color of the dispersions had become darker. It can be seen that pigment sedimentation was suppressed, resulting in a dispersion stabilization effect.

[0106] From the above results, it can be understood that the amide alcohol of formula (I) of the present invention exhibits a color development improving effect and / or good dispersion stability in various dispersions.

[0107] Examples of pigment dispersion compositions using the dispersant of the present invention are shown below. [Formulation Example 1] W / O Cream Foundation Composition Blend Amounts (wt%) 1. Hexyldecanol 10.0 2. Hexyl laurate 5.0 3. Polyglyceryl-2 dipolyhydroxystearate 3.0 4. Polyglyceryl-2 diisostearate 2.0 5. N-oleylhydroxyhexanamide 0.5 6. Titanium oxide / disodium stearoyl glutamate, aluminum hydroxide 8.3 7. Iron oxide / disodium stearoyl glutamate, aluminum hydroxide 1.7 8. Butylene Glycol 3.0 9. Pentylene glycol 3.0 10. Magnesium sulfate 2.0 11. Remaining water content <Manufacturing method> (1) Heat ingredients 1 and 5 to 80°C (2) Heat ingredients 2 to 4 to 75°C (3) Heat ingredients 8 to 11 to 75°C (4) Mix ingredients 1, 2, 6 and 7 and disperse at 75°C using a disperser (5) Add (3) to (4) and emulsify using a disperser (6) Cool slowly to room temperature while stirring to obtain a composition.

[0108] Formulation Example 2 Lip Gloss Composition Amounts (wt %) 1. Polyglyceryl-2 triisostearate 42.0 2. Hydrogenated castor oil isostearate 40.0 3. Octyldodecanol 10.0 4. Dextrin palmitate 5.0 5. Manganese violet 1.0 6. N-oleylhydroxyhexanamide 0.5 7. Tocopherol 0.1 <Manufacturing Method> (1) Heat ingredients 3 and 6. (2) Heat ingredients 1, 2, and 4 to 7. (3) Add (1) to (2) and dissolve uniformly with stirring. (4) Cool to obtain a composition.

[0109] [Formulation Example 3] UV Cream Composition (% by weight) 1. Isononyl isononanoate 42.0 2. Squalane 40.0 3. N-oleylhydroxyhexanamide 10.0 4. Polyglyceryl-2 isostearate 5.0 5. Zinc oxide / Dimethicone / Hydrogen dimethicone 1.0 6. Titanium oxide / Al hydroxide / Dimethicone / Hydrogen dimethicone 0.5 7. Pentylene glycol 0.1 8. Glycerin 5.0 9. Water / Sodium lactate 2.0 10. Remaining water <Manufacturing method> (1) Heat ingredients 1 to 4 (2) Heat ingredients 7 to 10 (3) Add ingredients 5 and 6 to (1) and stir while heating (4) Add (2) to (3) and stir while heating

[0110] Formulation Example 4 Eyeliner Composition Blend Amounts (wt%) 1. Carbon Black 25.0 2. Cyclopentasiloxane 20.0 3. Cyclopentasiloxane / Disteardimonium Hectorite / Propylene Carbonate 19.0 4. Cyclopentasiloxane / PEG / PPG-18 / 18 Dimethicone 10.0 5. Cetyl PEG / PEG-10 / 1 Dimethicone 3.0 6. N-Oleyl Hydroxyhexanamide 1.0 7. Water 16.3 8. Sodium Chloride 0.7 9. Cyclopentasiloxane / Trimethylsiloxysilicate 5.0 <Manufacturing Method> (1) Disperse raw materials 1 to 6 (2) Add raw materials 7 and 8 to (1) and disperse (3) Add raw material 9 to (2) and disperse (4) Obtain a composition

[0111] Formulation Example 5: Mascara Composition (% by weight) 1. Polyacrylate Emulsion 15.0 2. Ethylhexyl Palmitate 10.0 3. Hexyldecanol 10.0 4. Polyglyceryl-2 Isostearate / Dimer Dilinoleate Copolymer 10.0 5. Isododecane 6.0 6. Hydrogenated Castor Oil Dimer Dilinoleate 5.0 7. Paraffin Wax 5.0 8. Sorbitan Sesquiisostearate 4.0 9. Beeswax 3.0 10. Dextrin Palmitate 3.0 11. Carnauba Wax 2.0 12. N-Oleyl Hydroxyhexanamide 2.0 13. Ethylhexyl Methoxycinnamate 2.0 14. Stearic Acid 1.0 15. Glyceryl stearate 1.0 16. Black iron oxide 10.0 17. Water 11.0 <Production method> (1) Heat and dissolve ingredients 1 to 15. (2) Add ingredient 16 to (1) and disperse while heating. (3) Add ingredient 17 to (2) and disperse while heating. (4) Obtain a composition.

[0112] Formulation Example 6 Nail Polish Composition Ingredients (wt%) 1. Butyl acetate 32.0 2. Ethyl acetate 23.0 3. Nitrocellulose 15.0 4. Trimethylpentanyl diisobutyrate 10.0 5. Diacetone alcohol 5.0 6. Isopropanol 5.0 7. Stearalkonium bentonite 3.0 8. N-oleylhydroxyhexanamide 2.0 9. Mica 2.0 10. Camphor 1.0 11. Purified water 1.0 12. Red No. 202 0.8 13. Tocopherol 0.2 <Production method> (1) Mix 1 to 3 and 8 and disperse uniformly while stirring. (2) Add 4 to 7 in order and stir to form a uniform base. (3) Disperse pigments 9 and 12 in advance, add to (2) and mix uniformly. (4) Add 10, 11, and 13 in order and stir. (5) After filtering and cooling, a nail polish composition was obtained.

[0113] Formulation Example 7 Oil-based ink composition Blending amounts (wt %) 1. Ethanol 35.0 2. Benzyl alcohol 30.0 3. Iron oxide 20.0 4. Alkyd resin 14.5 5. N-oleylhydroxyhexanamide 0.5 <Production method> (1) Heat raw materials 1 to 5 (2) Dissolve (1) uniformly while stirring (3) Cool to obtain a composition.

[0114] Formulation Example 8 Water-based ink composition Blending amounts (wt%) 1. Ethanol 68.0 2. Water 15.0 3. Polyvinyl alcohol 10.0 4. Carbon black 5.0 6. N-oleylhydroxyhexanamide 1.5 7. Methylparaben 0.5 <Manufacturing method> (1) Heat ingredients 1 and 6 (2) Mix ingredients 2 to 5 and 7 (3) Add (2) little by little to (1) while stirring to obtain a uniform dispersion (4) Cool to room temperature while stirring to obtain a composition

[0115] Formulation Example 9 Composition for Inkjet Printer (Black Pigment Ink) Composition Blend Amounts (wt %) 1. Carbon Black MA-7 (pigment, manufactured by Mitsubishi Chemical Corporation) 5.0 2. Styrene-acrylic acid copolymer 1.0 3. Anionic resin emulsion 10.0 (as solids concentration) 4. Glycerin 10.0 5. Surfynol 465 (dispersant, manufactured by Air Product and Chemicals, Inc.) 1.0 6. Lauryl sulfobetaine (dispersant) 0.5 7. N-oleylhydroxyhexanamide (dispersant) 1.0 8. Remaining amount of ion-exchanged water <Manufacturing method> (1) Mix the pigment, dispersant, and water, and disperse the mixture in a sand mill (manufactured by Yaskawa Corporation) with glass beads (diameter 1.7 mm, 1.5 times the amount (weight) of the mixture) for 2 hours. (2) Remove the glass beads to obtain a pigment dispersion. (3) Mix the solvent excluding the pigment and dispersant to obtain an ink solvent, and gradually drop the ink solvent into the pigment dispersion while stirring, and stir at room temperature for 20 minutes. (4) Gradually drop the anionic resin emulsion dispersion, and stir and mix for 10 minutes at room temperature. (5) Filter through a 5 μm membrane filter to obtain an ink composition for inkjet printers.

[0116] Formulation Example 10 Toner composition for laser printers (black) Composition blending amounts (wt %) 1. Carbon black MA-100 (manufactured by Mitsubishi Chemical Corporation) 8.0 2. Refined carnauba wax No. 1 powder (manufactured by Nippon Wax Co., Ltd.) 5.0 3. Nichigo Polyester W-0223 (amorphous polyester resin, manufactured by Nippon Synthetic Chemical Industry Co., Ltd.) 85.0 4. Charge control agent T-77 (manufactured by Hodogaya Chemical Co., Ltd.) 1.0 5. N-oleylhydroxyhexanamide 1.0 <Production Method> (1) Preliminary mixing was performed using a Henschel mixer (FM10B manufactured by Mitsui Miike Chemical Engineering Co., Ltd.), followed by kneading using a twin-screw kneader (PCM-30 manufactured by Ikegai Corporation). (2) The above composition was melt-mixed using a Labo Plastomill Model 4M150 (manufactured by Toyo Seiki Seisakusho) at a jacket temperature of 150°C and a residence time of 3 minutes. (3) The molten resin was cooled to room temperature. (4) The mixture was finely pulverized using a supersonic jet pulverizer Labojet (manufactured by Nippon Pneumatic Mfg. Co., Ltd.). (5) The mixture was classified using an air classifier (MDS-I manufactured by Nippon Pneumatic Mfg. Co., Ltd.) to obtain toner particles with a particle size D50 of 8 μm. (6) 0.5 parts of colloidal silica (Aerosil R972, manufactured by Nippon Aerosil Co., Ltd.) was mixed with 100 parts of the toner particles using a sample mill to obtain a toner composition.

[0117] Formulation Example 11 Exterior Wall Paint Composition (wt%) 1. Toluene 40.0 2. Alkyd Resin 30.0 3. Titanium Oxide 15.0 4. Talc 5.0 5. Butyl Acetate 4.0 6. N-Oleyl Hydroxyhexanamide 3.0 7. Iron Oxide 2.0 8. Zirconium Naphthenate 1.0 <Manufacturing Method> (1) Add 6 to Raw Material 1 and heat. (2) Add Raw Materials 3, 4, and 7 to (1) in order and disperse with a disperser for 60 minutes. (3) Mix Raw Materials 2 and 5 separately and heat. (4) Add (2) to (3) and mix uniformly. (5) Add Raw Material 8 and mix uniformly with stirring to obtain a composition.

[0118] By employing the amide alcohol of formula (I), the present invention can provide a pigment dispersant, a pigment dispersion method, a pigment dispersion composition, and a method for producing a pigment dispersion composition.

Claims

1. Formula (I) In the formula R １ is a C6 to C22 hydrocarbon group, R ２ is H or a C6 to C22 hydrocarbon group, R ３ A pigment dispersant comprising an amide alcohol represented by the formula: wherein R is a linear or branched C2 to C21 hydrocarbon group.

2. The amide alcohol is represented by the formula (I), １ 2. The pigment dispersant according to claim 1, wherein is an amide alcohol which is a C6 to C22 unsaturated and / or branched hydrocarbon group.

3. (1) Formula (I) Formula (I) In the formula R １ is a C6 to C22 hydrocarbon group, R ２ is H or a C6 to C22 hydrocarbon group, R ３ (2) dissolving an amide alcohol represented by the following formula (1): wherein R is a linear or branched C2 to C21 hydrocarbon group in a solvent to obtain a mixture; and (3) mixing the pigment together with the mixture obtained in step (1) with a dispersion medium to dissolve the pigment.

4. The method according to claim 3, wherein the solvent in step (1) is hexyldecanol, isostearyl alcohol and / or octyldodecanol.

5. (A) Formula (I) In the formula R １ is a C6 to C22 hydrocarbon group, R ２ is H or a C6 to C22 hydrocarbon group, R ３ (B) a solvent; (C) a dispersion medium; and (D) a pigment, wherein the pigment dispersion composition does not contain a carboxyl group-containing polymer.

6. (A) Formula (I) In the formula R １ is a C6 to C22 hydrocarbon group, R ２ is H or a C6 to C22 hydrocarbon group, R ３ (B) a solvent selected from hexyldecanol, isostearyl alcohol, and octyldodecanol; (C) a dispersion medium; and (D) a pigment.

7. (1) Formula (I) In the formula R １ is a C6 to C22 hydrocarbon group, R ２ is H or a C6 to C22 hydrocarbon group, R ３ is a linear or branched C2 to C21 hydrocarbon group, in a solvent to obtain a mixture; (2) mixing and dispersing a pigment together with the mixture obtained in step (1) with a dispersion medium and any other components.

8. The pigment dispersion composition according to claim 7, wherein the solvent is hexyldecanol, isostearyl alcohol and / or octyldodecanol.

9. Formula (I) In the formula R １ is a C6 to C22 hydrocarbon group, R ２ is H or a C6 to C22 hydrocarbon group, R ３ is a linear or branched C2 to C21 hydrocarbon group; a dispersion medium; and a pigment, wherein the pigment dispersion composition is not an emulsion composition containing an aqueous phase and an oil phase.

10. The pigment dispersion composition according to any one of claims 5 to 9, wherein the pigment is finely powdered titanium oxide or finely powdered zinc oxide.

11. The pigment dispersion composition according to any one of claims 5 to 9, which is a coating composition.

12. The pigment dispersion composition according to any one of claims 5 to 9, which is a cosmetic composition.

13. A pigment comprising a compound represented by formula (I) In the formula R １ is a C6 to C22 hydrocarbon group, R ２ is H or a C6 to C22 hydrocarbon group, R ３ is a linear or branched C2 to C21 hydrocarbon group, and a dispersion medium, and dissolving the resulting pigment dispersion composition in the dispersion medium.

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