semi-permanent tattoos

Abstract

The present disclosure relates to semi-permanent tattoos, e.g., genipin-based ink compositions. In some embodiments, the ink compositions include genipin present in an amount of about 10% to about 20% w / w of the composition, a solvent present in an amount of about 65% to about 80% w / w of the composition, and one or more of a thickener, a humectant, and a film-forming agent present in an amount of 0.01% to about 10% w / w of the composition. In some embodiments, the compositions further include a preservative.

Description

[Technical Field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims priority to U.S. Provisional Patent Application No. 63 / 037,381, filed June 10, 2020, which is incorporated herein by reference in its entirety.

[0002] The present invention relates to semi-permanent tattoos, and more particularly to genipin-based ink compositions and the application of such compositions to the skin using a pen-like applicator. [Background technology]

[0003] Temporary or semi-permanent tattoos or body inks have been used throughout human history to decorate the body. Generally, temporary or semi-permanent tattoos are transferred to the skin by directly exposing the skin to the tattoo ink for a specified incubation period. The quality of the transferred image and its duration on the skin can depend on the ink distribution profile in the outer layer of the skin, called the stratum corneum. Current manufacturing processes for pre-made tattoo designs include the use of flexographic or gravure printing, stencils, and inkjet printers. However, due to the barrier properties of the stratum corneum, many current methods require significant end-user supervision during the tattoo application process to ensure adequate ink delivery to the skin for proper color development. Summary of the Invention

[0004] Provided herein are compositions comprising a semi-permanent colorant, a solvent, and a thickener. Also provided herein are compositions comprising a semi-permanent colorant, a solvent, and a film-forming agent.

[0005] In some embodiments, the semi-permanent coloring agent is present in an amount of about 10% to about 20% w / w of the composition. In some embodiments, the semi-permanent coloring agent is present in an amount of about 12% to about 16% w / w of the composition. In some embodiments, the semi-permanent coloring agent is present in an amount of about 14% w / w of the composition. In some embodiments, the semi-permanent coloring agent is genipin.

[0006] In some embodiments, the semi-permanent coloring agent is present in an amount of about 5% to about 15% w / w of the composition. In some embodiments, the semi-permanent coloring agent is present in an amount of about 9% to about 11% w / w of the composition. In some embodiments, the semi-permanent coloring agent is present in an amount of about 10% w / w of the composition. In some embodiments, the semi-permanent coloring agent is genipin.

[0007] In some embodiments, the solvent is present in an amount of about 65% to about 80% w / w of the composition. In some embodiments, the solvent is present in an amount of about 72% to about 76% w / w of the composition. In some embodiments, the solvent is present in an amount of about 75% to about 7680 w / w of the composition. In some embodiments, the solvent is present in an amount of about 74% w / w of the composition. In some embodiments, the solvent is present in an amount of about 77% w / w of the composition. In some embodiments, the solvent comprises water, methanol, ethanol, isopropanol, diethylene glycol monoethyl ether, or a combination thereof.

[0008] In some embodiments, the solvent is a combination of water and ethanol. In some such embodiments, water is present in an amount of about 25% to about 30% w / w of the composition. In some such embodiments, water is present in an amount of about 28% w / w of the composition. In some such embodiments, ethanol is present in an amount of about 40% to about 50% w / w of the composition. In some such embodiments, ethanol is present in an amount of about 45% to about 47% w / w of the composition. In some such embodiments, ethanol is present in an amount of about 46% w / w of the composition.

[0009] In some embodiments, the solvent is a combination of water and ethanol. In some such embodiments, water is present in an amount of about 25% to about 35% w / w of the composition. In some such embodiments, water is present in an amount of about 30% w / w of the composition. In some such embodiments, ethanol is present in an amount of about 40% to about 55% w / w of the composition. In some such embodiments, ethanol is present in an amount of about 45% to about 50% w / w of the composition. In some such embodiments, ethanol is present in an amount of about 48% w / w of the composition.

[0010] In some embodiments, the composition further comprises a thickening agent. In some embodiments, the thickening agent is present in an amount of about 0.01% to about 0.3% w / w of the composition. In some embodiments, the thickening agent is present in an amount of about 0.05% to about 0.2% w / w of the composition. In some embodiments, the thickening agent is present in an amount of about 0.12% w / w of the composition. In some embodiments, the thickening agent comprises hydroxyethyl cellulose, xanthan gum, arabinogalactan, aluminum starch octenylsuccinate, xanthan gum, sclerotium gum, tragacanth gum, pectin, karaya gum, gum arabic, agar, guar gum, carrageenan, locust bean gum, alginate, arginine, gelatin, tara gum, ghatti gum, gellan gum, konjac gum, cassia gum, spruce gum, chicle gum, dammar, curdlan gum, pullulan, hydroxypropyl cellulose, hydroxypropyl methylcellulose, ethyl cellulose, soybean hemicellulose, sodium carboxymethylcellulose, or combinations thereof.

[0011] In some embodiments, the thickening agent is a combination of hydroxyethyl cellulose and xanthan gum. In some such embodiments, the hydroxyethyl cellulose is present in an amount of about 0.01% to about 0.1% w / w of the composition. In some such embodiments, the hydroxyethyl cellulose is present in an amount of about 0.04% to about 0.08% w / w of the composition. In some such embodiments, the hydroxyethyl cellulose is present in an amount of about 0.06% w / w of the composition. In some such embodiments, the xanthan gum is present in an amount of about 0.01% to about 0.1% w / w of the composition. In some such embodiments, the xanthan gum is present in an amount of about 0.04% to about 0.08% w / w of the composition. In some such embodiments, the xanthan gum is present in an amount of about 0.06% w / w of the composition.

[0012] In some embodiments, the composition further comprises a film-forming agent. In some embodiments, the film-forming agent is present in an amount of about 0.1% to about 10% w / w of the composition. In some embodiments, the film-forming agent is present in an amount of about 5% to about 10% w / w of the composition. In some embodiments, the film-forming agent is present in an amount of about 4% to about 6% w / w of the composition. In some embodiments, the film-forming agent is present in an amount of about 6% to about 9% w / w of the composition. In some embodiments, the film-forming agent is present in an amount of about 5% w / w of the composition. In some embodiments, the film-forming agent is present in an amount of about 7.55% w / w of the composition. In some embodiments, the film-forming agent comprises a volatile silicone resin, polyvinylpyrrolidone, acrylate, acrylamide, copolymer, isododecane resin, or a combination thereof. In some embodiments, the film former is selected from the group consisting of polymethylsilsesquioxane, trimethylsiloxysilicate, polypropylsilsesquioxane, dimethicone, cyclopentasiloxane, dimethiconol crosspolymer, polysilicone-6, polysilicone-8, polysilicone-11, polysilicone-14, acrylate copolymer, styrene / acrylate copolymer, polyvinylpyrrolidone, acrylates / C12-22 alkyl methacrylate copolymer, acrylates / polytrimethylsiloxymethacrylate copolymer, polyvinylpyrrolidone / vinyl acetate (VP / VA) copolymer, VP / acrylate copolymer, polyvinylpyrrolidone / vinyl acetate (VP / VA) ... and / or a combination thereof.

[0013] In some embodiments, the film-forming agent is a combination of polymethylsilsesquioxane and an acrylate / C12-22 alkyl methacrylate copolymer. In some embodiments, the polymethylsilsesquioxane is present in an amount of about 1% to about 5% w / w of the composition. In some embodiments, the polymethylsilsesquioxane is present in an amount of about 2% w / w of the composition. In some embodiments, the acrylate / C12-22 alkyl methacrylate copolymer is present in an amount of about 1% to about 5% w / w of the composition. In some such embodiments, the acrylate / C12-22 alkyl methacrylate copolymer is present in an amount of about 3% w / w of the composition.

[0014] In some embodiments, the film-forming agent is a combination of an acrylate copolymer, polyvinylpyrrolidone, and a styrene / acrylate copolymer. In some such embodiments, the acrylate copolymer is present in an amount of about 0.1% to about 10% w / w of the composition. In some such embodiments, the acrylate copolymer is present in an amount of about 0.1% to about 1% w / w of the composition. In some such embodiments, the acrylate copolymer is present in an amount of about 0.25% w / w of the composition. In some such embodiments, the polyvinylpyrrolidone is present in an amount of about 0.1% to about 10% w / w of the composition. In some such embodiments, the polyvinylpyrrolidone is present in an amount of about 0.5% to about 1.5% w / w of the composition. In some such embodiments, the polyvinylpyrrolidone is present in an amount of about 1% w / w of the composition. In some such embodiments, the styrene / acrylate copolymer is present in an amount of about 0.1% to about 10% w / w of the composition. In some such embodiments, the styrene / acrylate copolymer is present in an amount of about 5% to about 7% w / w of the composition, hi some such embodiments, the styrene / acrylate copolymer is present in an amount of about 6% w / w of the composition.

[0015] In some embodiments, the composition further comprises a humectant. In some embodiments, the humectant is present in an amount of about 0.1% to about 10% w / w of the composition. In some embodiments, the humectant is present in an amount of about 1% to about 10% w / w of the composition. In some embodiments, the humectant is present in an amount of about 2% to about 6% w / w of the composition. In some embodiments, the humectant is present in an amount of about 0.5% to about 1.5% w / w of the composition. In some embodiments, the humectant is present in an amount of about 4% w / w of the composition. In some embodiments, the humectant is present in an amount of about 1% w / w of the composition. In some embodiments, the moisturizer includes aloe vera gel, lithium chloride, allantoin, urea, dicyanamidoglycerol, lactic acid, propylene glycol, polyethylene glycol, dipropylene glycol, polypropylene glycol, polyethylene glycol and its derivatives, propanediol, hexylene glycol, 1,3-butylene glycol, 1,2,6-hexanetriol, ethoxylated glycerol, propoxylated glycerol, glyceryl triacetate, sorbitol, hydroxypropyl sorbitol, xylitol, maltitol, hyaluronic acid, Tremella extract, sodium lactate, sodium L-pyroglutamate urea, pyrrolidone carboxylic acid, or a combination thereof. In some embodiments, the moisturizer is glycerin. In some embodiments, the moisturizer is propanediol.

[0016] In some embodiments, the composition further comprises a preservative. In some embodiments, the preservative is present in an amount of about 0.1% to about 5% w / w of the composition. In some embodiments, the preservative is present in an amount of about 2% to about 4% w / w of the composition. In some embodiments, the preservative is present in an amount of about 0.5% to about 1.5% w / w of the composition. In some embodiments, the preservative is present in an amount of about 3% w / w of the composition. In some embodiments, the preservative is present in an amount of about 1.05% w / w of the composition. In some embodiments, the preservative is ascorbic acid, ascorbate, palmitate, citric acid, benzoate, benzoic acid, propionate, propionic acid, sorbate, sorbic acid, salicylic acid, salicylate, hexa-2,4-dienoic acid, hexa-2,4-dienoate, formaldehyde, formaldehyde-releasing agents, formic acid and its salts, 3-acetyl-6-methylpyran-2,4-(3H)-dione and its salts, 3,3'-dibromo-4,4'-hexamethylenedioxydibenzamidine and its salts, thiomersal, phenylmercury salts, undec-10-enoic acid and its salts, 1,3-bis(2-ethylhexyl)hexa Hydro-5-methyl-5-pyrimidine, 5-bromo-5-nitro-1,3-dioxane, bronopol, 2,4-dichlorobenzyl alcohol, 1-(4-chlorophenyl)-3-(3,4-dichlorophenyl)urea, chlorocresol, chloroxylenol, 5-chloro-2-(2,4-dichlorophenoxy)phenol, N,N”-methylenebis[N'-[3-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]urea], polyaminopropyl biguanide, methenamine, quaternium-15, climbazole, DMDM ​​hydantoin, benzyl alcohol, 1-hydroxy-4-methyl-6-(2,4,4-Trimethylpentyl)-2-pyridone, piroctone olamine, bromochlorophene, o-cymen-5-ol, chlorophene, chloroacetamine, methylchloroisothiazolinone, methylisothiazolinone, phenoxyisopropanol, chlorhexidine, chlorhexidine diacetate, chlorhexidine digluconate, chlorhexidine dihydrochloride, dimethyloxazolidine, behentrimonium chloride, cetrimonium bromide, cetrimonium chloride, laurtrimonium bromide, laurtrimonium chloride, steartrimonium bromide, steartrimonium chloride, diazolidinyl urea, hexamidine, hexamidine diisethionate, hexamidine paraben, glutaral, 7-ethylbicyclooxazolidine, chlorphenesin, sodium hydroxymethylglycine, silver chloride, salt Benzethonium chloride, benzalkonium chloride, benzalkonium bromide, benzalkonium saccharinate, benzyl hemiformal, iodopropynyl butylcarbamate, biphenyl-2-ol and its salts, zinc pyrithione, erythorbate, nitrous acid, ethylenediaminetetraacetic acid (EDTA), butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), caprylic acid, dilauryl thiodipropionate, erythorbic acid, guaiac butter, methylparaben, sulfite, bisulfite, metabisulfite, propylparaben, stannous chloride, sulfur dioxide, thiodipropionic acid, isothiazolinone, parabens, phenoxyethanol, ethylhexylglycerin, glycol, tocopherol, 1,2-hexanediol, or combinations thereof.

[0017] In some embodiments, the preservative comprises a combination of phenoxyethanol and ethylhexylglycerin. In some such embodiments, the phenoxyethanol and ethylhexylglycerin are present in the composition in a ratio of about 9:1 phenoxyethanol:ethylhexylglycerin. In some such embodiments, the combination of phenoxyethanol and ethylhexylglycerin is present in an amount of about 0.1% to about 2% w / w of the composition. In some such embodiments, the combination of phenoxyethanol and ethylhexylglycerin is present in an amount of about 1% w / w of the composition.

[0018] In some embodiments, the preservative comprises 1,2-hexanediol. In some embodiments, the 1,2-hexanediol is present in an amount of about 1% to about 3% w / w of the composition. In some embodiments, the 1,2-hexanediol is present in an amount of about 2% w / w of the composition.

[0019] In some embodiments, where the preservative comprises a combination of phenoxyethanol and ethylhexylglycerin, the preservative further comprises EDTA. In some embodiments, the EDTA is present in an amount of about 0.01% to about 0.5% w / w of the composition. In some embodiments, the EDTA is present in an amount of about 0.05% w / w of the composition.

[0020] Also provided herein is a method of making an ink composition, the method including: (i) combining a thickener with a first solvent to form a first solution; (ii) combining genipin with a second solvent to form a second solution; and (iii) combining the first solution and the second solution to form the ink composition.

[0021] In some embodiments, the methods described herein further include adding a film-forming agent, a preservative, or a combination thereof to the ink composition.

[0022] Also provided herein is a method of making an ink composition, the method including: (i) combining a thickener and a humectant with a first solvent to form a first solution; (ii) combining genipin and a first film-forming agent with a second solvent to form a second solution; and (iii) combining the first solution and the second solution to form the ink composition.

[0023] In some embodiments, the methods described herein further include adding a second film-forming agent, a preservative, or a combination thereof to the ink composition.

[0024] In some embodiments, the first solution is incubated at a temperature of about 70° C. to about 120° C. In some embodiments, the first solution is incubated at a temperature of about 90° C. to about 95° C. In some embodiments, the first solution is stirred.

[0025] In some embodiments, the thickening agent is dissolved in the first solution prior to combining the first and second solutions.

[0026] In some embodiments, the second solution is incubated at a temperature of about 30° C. to about 60° C. In some embodiments, the second solution is incubated at a temperature of about 40° C. to about 50° C. In some embodiments, the second solution is stirred.

[0027] In some embodiments, the first solution is cooled to a temperature of about 20°C to about 50°C. In some embodiments, the first solution is cooled to a temperature of about 40°C. In some embodiments, the second solution is cooled to a temperature of about 20°C to about 50°C. In some embodiments, the second solution is cooled to a temperature of about 40°C.

[0028] In some embodiments, the ink composition is agitated.

[0029] In some embodiments, the ink composition is cooled to a temperature of about 20°C to about 30°C. In some embodiments, the ink composition is cooled to a temperature of about 25°C.

[0030] In some embodiments, the ink composition is cooled before adding the film-forming agent, preservative, or a combination thereof to the ink composition.

[0031] In some embodiments, the thickening agent and first solvent are present in the first solution in a ratio of thickening agent:first solvent of about 1:500 to about 4:500, hi some embodiments, the thickening agent and first solvent are present in the first solution in a ratio of thickening agent:first solvent of about 2:500.

[0032] In some embodiments, the first solvent comprises water, methanol, ethanol, isopropanol, diethylene glycol monoethyl ether, or a combination thereof, hi some embodiments, the first solvent comprises water.

[0033] In some embodiments, the thickening agent comprises hydroxyethyl cellulose, xanthan gum, arabinogalactan, aluminum starch octenyl succinate, xanthan gum, sclerotium gum, tragacanth gum, pectin, karaya gum, gum arabic, agar, guar gum, carrageenan, locust bean gum, alginate, arginine, gelatin, tara gum, ghatti gum, gellan gum, konjac gum, cassia gum, spruce gum, chicle gum, dammar, curdlan gum, pullulan, hydroxypropyl cellulose, hydroxypropylmethylcellulose, ethylcellulose, soybean hemicellulose, sodium carboxymethylcellulose, or a combination thereof. In some embodiments, the thickening agent is a combination of hydroxyethyl cellulose and xanthan gum. In some embodiments, the combination of hydroxyethyl cellulose and xanthan gum is present in a 1:1 hydroxyethyl cellulose:xanthan gum ratio.

[0034] In some embodiments, the thickening agent, humectant, and first solvent are present in the first solution in a ratio of thickening agent:humectant:first solvent of about 1:15:234 to about 1:62:187.

[0035] In some embodiments, the thickening agent and first solvent are present in the first solution in a ratio of thickening agent:humectant:first solvent of about 1:31:218.

[0036] In some embodiments, the moisturizer comprises aloe vera gel, lithium chloride, allantoin, urea, dicyanamidoglycerol, lactic acid, propylene glycol, polyethylene glycol, dipropylene glycol, polypropylene glycol, polyethylene glycol and its derivatives, hexylene glycol, 1,3-butylene glycol, 1,2,6-hexanetriol, ethoxylated glycerol, propoxylated glycerol, glyceryl triacetate, sorbitol, hydroxypropyl sorbitol, xylitol, maltitol, hyaluronic acid, Tremella extract, sodium lactate, sodium L-pyroglutamate urea, and pyrrolidone carboxylic acid, or a combination thereof. In some embodiments, the moisturizer is glycerin.

[0037] In some embodiments, the genipin and second solvent are present in the second solution in a ratio of genipin:second solvent of about 4:25 to about 3:5. In some embodiments, the genipin and second solvent are present in the second solution in a ratio of genipin:second solvent of about 3:10.

[0038] In some embodiments, the second solvent comprises water, methanol, ethanol, isopropanol, diethylene glycol monoethyl ether, or a combination thereof, hi some embodiments, the second solvent comprises ethanol.

[0039] In some embodiments, the genipin, first film-forming agent, and second solvent are present in the second solution in a ratio of genipin:film-forming agent:second solvent of about 57:16:177 to about 57:4:189.

[0040] In some embodiments, the genipin, first film-forming agent, and second solvent are present in the second solution in a ratio of genipin:film-forming agent:second solvent of about 57:8:185.

[0041] In some embodiments, the first film-forming agent is polymethylsilsesquioxane, trimethylsiloxysilicate, polypropylsilsesquioxane, dimethicone, cyclopentasiloxane, dimethiconol crosspolymer, polysilicone-6, polysilicone-8, polysilicone-11, polysilicone-14, acrylates / C12-22 alkyl methacrylate copolymer, acrylates / polytrimethylsiloxymethacrylate copolymer, polyvinylpyrrolidone / vinyl acetate (VP / VA) copolymer, VP / dimethiconyl acrylate / polycarbamyl In some embodiments, the first film-forming agent is selected from the group consisting of VP / polyglycol ester, VP / dimethylaminoethyl methacrylate copolymer, VP / dimethylaminoethyl methacrylate / polycarbamyl polyglycol ester, VP / eicosene copolymer, VP / hexadecene copolymer, VP / methacrylamide / vinylimidazole copolymer, VP / polycarbamyl polyglycol ester, VP / VA copolymer, polyester-1, polyester-2, polyester-3, polyester-4, polyester-5, polyester-7, polyester-8, polyester-10, or combinations thereof. In some embodiments, the first film-forming agent is polymethylsilsesquioxane.

[0042] In some embodiments, the first solution and the second solution are present in the ink composition in a ratio of first solution:second solution of about 1:4 to about 1:1.

[0043] In some embodiments, the first solution and the second solution are present in the ink composition in a ratio of about 1:2 first solution:second solution.

[0044] In some embodiments, the film-forming agent is present in an amount of about 1% to about 10% w / w of the ink composition. In some embodiments, the film-forming agent is present in an amount of about 2% to about 6% w / w of the ink composition. In some embodiments, the film-forming agent comprises a volatile silicone resin, polyvinylpyrrolidone, acrylate, acrylamide, copolymer, isododecane resin, or a combination thereof. In some embodiments, the film-forming agent is polymethylsilsesquioxane, trimethylsiloxysilicate, polypropylsilsesquioxane, dimethicone, cyclopentasiloxane, dimethiconol crosspolymer, polysilicone-6, polysilicone-8, polysilicone-11, polysilicone-14, acrylates / C12-22 alkyl methacrylate copolymer, acrylates / polytrimethylsiloxymethacrylate copolymer, polyvinylpyrrolidone / vinyl acetate (VP / VA) copolymer, VP / dimethiconyl acrylate / polycarbamyl / poly In some embodiments, the film-forming agent is selected from the group consisting of polymethylsilsesquioxane, acrylates / C12-22 alkyl methacrylate copolymer, and combinations thereof.

[0045] In some embodiments, the second film-forming agent is present in an amount of about 1% to about 5% w / w of the ink composition. In some embodiments, the second film-forming agent is present in an amount of about 3% w / w of the ink composition. In some embodiments, the second film-forming agent is selected from the group consisting of polymethylsilsesquioxane, trimethylsiloxysilicate, polypropylsilsesquioxane, dimethicone, cyclopentasiloxane, dimethiconol crosspolymer, polysilicone-6, polysilicone-8, polysilicone-11, polysilicone-14, acrylates / C12-22 alkyl methacrylate copolymer, acrylates / polytrimethylsiloxymethacrylate copolymer, polyvinylpyrrolidone / vinyl acetate (VP / VA) copolymer, and VP / dimethiconyl acrylate / polycarbamyl. In some embodiments, the second film former comprises acrylates / C12-22 alkyl methacrylate copolymer, VP / polyglycol ester, VP / dimethylaminoethyl methacrylate copolymer, VP / dimethylaminoethyl methacrylate / polycarbamyl polyglycol ester, VP / eicosene copolymer, VP / hexadecene copolymer, VP / methacrylamide / vinylimidazole copolymer, VP / polycarbamyl polyglycol ester, VP / VA copolymer, polyester-1, polyester-2, polyester-3, polyester-4, polyester-5, polyester-7, polyester-8, polyester-10, or a combination thereof. In some embodiments, the second film former is an acrylates / C12-22 alkyl methacrylate copolymer.

[0046] In some embodiments, the preservative is present in an amount of about 0.1% to about 5% w / w of the ink composition. In some embodiments, the preservative is present in an amount of about 2% to about 4% w / w of the ink composition. In some embodiments, the preservative is present in an amount of about 3% w / w of the ink composition. In some embodiments, the preservative is ascorbic acid, ascorbate, palmitate, citric acid, benzoate, benzoic acid, propionate, propionic acid, sorbate, sorbic acid, salicylic acid, salicylate, hexa-2,4-dienoic acid, hexa-2,4-dienoate, formaldehyde, formaldehyde-releasing agents, formic acid and its salts, 3-acetyl-6-methylpyran-2,4-(3H)-dione and its salts, 3,3'-dibromo-4,4'-hexamethylenedioxydibenzamidine and its salts, thiomersal, phenylmercury salts, undec-10-enoic acid and its salts, 1,3-bis(2-ethylhexyl)hexa Hydro-5-methyl-5-pyrimidine, 5-bromo-5-nitro-1,3-dioxane, bronopol, 2,4-dichlorobenzyl alcohol, 1-(4-chlorophenyl)-3-(3,4-dichlorophenyl)urea, chlorocresol, chloroxylenol, 5-chloro-2-(2,4-dichlorophenoxy)phenol, N,N”-methylenebis[N'-[3-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]urea], polyaminopropyl biguanide, methenamine, quaternium-15, climbazole, DMDM ​​hydantoin, benzyl alcohol, 1-hydroxy-4-methyl-6-(2,4,4-Trimethylpentyl)-2-pyridone, piroctone olamine, bromochlorophene, o-cymen-5-ol, chlorophene, chloroacetamine, methylchloroisothiazolinone, methylisothiazolinone, phenoxyisopropanol, chlorhexidine, chlorhexidine diacetate, chlorhexidine digluconate, chlorhexidine dihydrochloride, dimethyloxazolidine, behentrimonium chloride, cetrimonium bromide, cetrimonium chloride, laurtrimonium bromide, laurtrimonium chloride, steartrimonium bromide, steartrimonium chloride, diazolidinyl urea, hexamidine, hexamidine diisethionate, hexamidine paraben, glutaral, 7-ethylbicyclooxazolidine, chlorphenesin, sodium hydroxymethylglycine, silver chloride, salt The preservative may be selected from the group consisting of benzethonium chloride, benzalkonium chloride, benzalkonium bromide, benzalkonium saccharinate, benzyl hemiformal, iodopropynyl butylcarbamate, biphenyl-2-ol and its salts, zinc pyrithione, erythorbate, nitrous acid, ethylenediaminetetraacetic acid (EDTA), butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), caprylic acid, dilauryl thiodipropionate, erythorbic acid, guaiac butter, methylparaben, sulfite, bisulfite, metabisulfite, propylparaben, stannous chloride, sulfur dioxide, thiodipropionic acid, isothiazolinone, parabens, phenoxyethanol, ethylhexylglycerin, glycol, tocopherol, 1,2-hexanediol, or a combination thereof. In some embodiments, the preservative may be a combination of phenoxyethanol and ethylhexylglycerin.

[0047] In some embodiments, the phenoxyethanol and ethylhexylglycerin are present in the composition in a ratio of about 9:1 phenoxyethanol:ethylhexylglycerin. In some embodiments, the combination of phenoxyethanol and ethylhexylglycerin is present in an amount of about 0.1% to about 2% w / w of the ink composition. In some embodiments, the combination of phenoxyethanol and ethylhexylglycerin is present in an amount of about 1% w / w of the ink composition.

[0048] In some embodiments, the preservative comprises 1,2-hexanediol. In some embodiments, the 1,2-hexanediol is present in an amount of about 1% to about 3% w / w of the ink composition. In some embodiments, the 1,2-hexanediol is present in an amount of about 2% w / w of the ink composition.

[0049] Also provided herein are ink compositions prepared by any of the methods described herein.

[0050] As used herein, "temporary colorant" refers to a colorant that, if placed on or penetrates the skin, diffuses from the skin or can be washed away, for example, by water, soap, and / or isopropanol.

[0051] As used herein, "color" refers to wavelengths of electromagnetic radiation visible to the human eye.

[0052] As used herein, "colorant" refers to a substance that changes the color of reflected or transmitted light as a result of wavelength-selective absorption.

[0053] Reference to the term "about" has its ordinary meaning in the context of a composition to allow for reasonable variation in amounts that can achieve the same effect, and herein also refers to values ​​plus or minus 10% of the provided value. For example, "about 20" means or includes an amount from 18 to 22, inclusive.

[0054] The details of one or more embodiments of the invention are set forth in the description below. Other features, objects, and advantages of the invention will become apparent from the description, and from the claims. DETAILED DESCRIPTION OF THE INVENTION

[0055] This document provides ink compositions, such as genipin-based ink compositions, that can be applied to skin as semi-permanent tattoos. Accordingly, the ink compositions are formulated so that the ink is safe for contact with skin and maintains stability or skin transferability throughout the product's shelf life. The longevity of a semi-permanent tattoo, or the residence time of a semi-permanent colorant on the skin, can be limited by the natural skin desquamation process and the thickness of each layer of skin (the thickness of the epidermis can depend on the region of the body). In some embodiments, the ink compositions described herein can be suitable for application to skin using a pen-like applicator.

[0056] In some embodiments, the ink compositions provided herein comprise a semi-permanent colorant, a solvent, and a thickener. In some embodiments, the ink compositions provided herein comprise a semi-permanent colorant, a solvent, and a humectant. In some embodiments, the ink compositions provided herein comprise a semi-permanent colorant, a solvent, a thickener, and a humectant. In some embodiments, the composition further comprises a film former. In some embodiments, the ink compositions provided herein comprise a semi-permanent colorant, a solvent, and a film former.

[0057] As used herein, a "semi-permanent colorant" refers to a colorant that penetrates one or more layers of the skin and cannot be removed from the skin without physical destruction or natural desquamation. For example, a semi-permanent colorant may penetrate the stratum corneum and react with other molecules, such as other colorant molecules and / or other molecules present in the stratum corneum, immobilizing the semi-permanent colorant within the stratum corneum. For example, a semi-permanent colorant may crosslink with collagen found in the stratum corneum. In some embodiments, a semi-permanent colorant may react with other molecules, such as other colorant molecules and / or other molecules present in the stratum corneum, to form molecules that are too large to diffuse out of the stratum corneum. In some embodiments, in which a semi-permanent colorant penetrates the stratum corneum, the residence time of the colorant is determined by the natural skin desquamation process. In some embodiments, a semi-permanent colorant cannot be washed off, for example, with water, soap, and / or isopropanol. In some embodiments, a semi-permanent colorant comprises a natural or synthetic pigment or dye. In some embodiments, the semi-permanent colorant can include a colorant precursor, for example, a molecule such as genipin that develops color upon reaction with one or more other molecules.

[0058] In some embodiments, the semi-permanent colorant (e.g., genipin) is present in an amount of about 0.1% to about 25% w / w of the composition, e.g., about 0.1% to about 24%, about 0.1% to about 22%, about 0.1% to about 20%, about 0.1% to about 18%, about 0.1% to about 16%, about 0.1% to about 14%, about 0.1% to about 12%, about 0.1% to about 10%, about 0.1% to about 8%, about 0.1% to about 6%, about 0.1% to about 4%, about 0.1 In some embodiments, the semi-permanent colorant (e.g., genipin) is present in an amount of about 5% to about 15%, about 10% to about 15%, about 10% to about 20%, about 15% to about 20%, about 8% to about 12%, about 10% to about 14%, about 12% to about 16%, about 14% to about 18%, or about 16% to about 20% w / w of the composition. In some embodiments, the semi-permanent coloring agent (e.g., genipin) is present in an amount of about 12% to about 16% w / w of the composition. In some embodiments, the semi-permanent coloring agent (e.g., genipin) is present in an amount of about 9% to about 11% w / w of the composition. In some embodiments, the semi-permanent coloring agent (e.g., genipin) is present in an amount of about 1%, about 2%, about 3%, about 4%, about 4.5%, about 5%, about 5.5%, about 6%, about 6.5%, about 7%, about 7.5%, about 8%, about 8.5%, about 9%, about 9.5%, about 10%, about 10.5%, about 11%, about 11.5%, about 12%, about 12.5%, about 13%, about 13.5%, about 14%, about 15%, about 16%, about 17%, about 18%, about 19%, about 20%, about 21%, about 22%, about 23%, about 24%, or about 25% w / w of the composition. In some embodiments, the semi-permanent coloring agent (e.g., genipin) is present in an amount of about 14% w / w of the composition. In some embodiments, the semi-permanent coloring agent (eg, genipin) is present in an amount of about 10% w / w of the composition.

[0059] In some embodiments, the semi-permanent colorant comprises a colorant precursor. In some embodiments, the colorant precursor is genipin. Thus, in some embodiments, the semi-permanent colorant is genipin. In some embodiments, the semi-permanent colorant is purified genipin.

[0060] As used herein, "genipin" refers to genipin extract, partially purified genipin extract, and / or purified genipin, as further described herein. Genipin is derived from an iridoid glycoside called geniposide, which is present in nearly 40 plant species. Additionally, genipin is a precursor to gardenia blue, which undergoes free radical polymerization and / or oligomerization reactions upon exposure to amine groups to form a blue colorant (see, e.g., Touyama et al., Chem. Pharm. Bull. 42:668-673, 1994 and Touyama et al., Chem. Pharm. Bull. 42(8):1571-1578, 1994, both incorporated herein by reference in their entireties). Upon contact with skin, genipin can react with amines in the skin to produce polymer-based and / or oligomer-based blue colors in situ. Because polymeric and / or oligomeric blue colorants are too large to penetrate the skin at relevant concentrations, the penetration profile of genipin may determine the color density profile of the stratum corneum. For example, the average molecular weight of polymeric and / or oligomeric blue colorants has been reported to be 8,900±600 daltons, and polymeric and / or oligomeric blue colorants may contain 40 to 44 monomer units (see, e.g., Touyama et al., Chem. Pharm. Bull. 42:668-673, 1994). In some embodiments, the average molecular weight of a blue colorant, such as polymerized and / or oligomerized genipin produced from exposure of genipin present in the compositions described herein to an amine, may range from about 500 daltons to about 15,000 daltons. In some embodiments, the average molecular weight of polymerized and / or oligomerized genipin may range from about 500 daltons to about 15,000 daltons. In some embodiments, genipin of different molecular weights (e.g., including polymerized and / or oligomerized genipin) can be produced from exposure of genipin present in the compositions described herein to amines. For example, in some embodiments, polymerized and / or oligomerized genipin can have an average molecular weight of about 500 daltons to about 15,000 daltons.In some embodiments, polymerized and / or oligomerized genipin can have an average molecular weight of about 500 to about 1000 daltons, about 500 to about 1500 daltons, about 1000 to about 2000 daltons, about 1500 to about 2500 daltons, about 2000 to about 3500 daltons, 3500 to about 5000 daltons, 5000 to about 6500 daltons, about 6000 to about 8300 daltons, or about 8300 to about 9500 daltons, and combinations thereof.

[0061] The presence of amines, such as those endogenously present in plant extracts or exogenously introduced amines, in genipin solutions can pose shelf-life stability challenges. For example, over time, reactive precursors can develop into blue semi-permanent colorants (e.g., polymerized and / or oligomerized genipin) before application to the skin, limiting the penetration of the semi-permanent colorant into the stratum corneum. Penetration of genipin into deeper layers of the stratum corneum can allow subsequent color development and retention of the polymer-based and / or oligomer-based blue semi-permanent colorant in the skin, potentially leading to increased longevity of the semi-permanent tattoo. Subsequently, the longevity of the semi-permanent tattoo, or the residence time of the semi-permanent colorant in the skin, can be limited by natural skin desquamation processes. In some embodiments, purified genipin has a purity of greater than about 85% w / w of the genipin composition. For example, purified genipin has a purity of greater than about 86%, about 88%, about 90%, about 92%, about 94%, about 96%, about 98%, about 99%, or about 99.5% w / w of the genipin composition.

[0062] Non-limiting examples of solvents include water, methanol, ethanol, isopropanol, and diethylene glycol monoethyl ether. In some embodiments, the solvent is a volatile solvent, e.g., the solvent can evaporate or vaporize at room temperature. Non-limiting examples of volatile solvents include water, methanol, ethanol, and isopropanol. In some embodiments, the solvent is selected to have a low toxicity profile when used as described herein. For example, the solvent can be selected so that the amount of any residual solvent remaining after the ink composition has dried on the applicator does not result in a toxic amount upon contact with a human skin surface.

[0063] In some embodiments, the solvent is present in an amount of about 1% to about 95% w / w of the composition, e.g., about 10% to about 95%, about 20% to about 95%, about 30% to about 95%, about 40% to about 95%, about 50% to about 95%, about 60% to about 95%, about 70% to about 95%, about 80% to about 95%, about 1% to about 20%, about 1% to about 30%, about 1% to about 40%, about 1% to about 50%, about 1% to about 60%, about 1% to about 70%, about 1% to about 80%, or about 1% to about 90% w / w of the composition. In some embodiments, the solvent is present in an amount of about 50% to about 75%, about 55% to about 80%, about 60% to about 85%, about 65% to about 90%, about 55% to about 75%, about 60% to about 80%, about 65% to about 85%, about 70% to about 90%, about 75% to about 95%, about 60% to about 70%, about 65% to about 75%, about 70% to about 80%, or about 75% to about 85% w / w of the composition. For example, the solvent may be present in an amount of about 60% to about 65%, about 62% to about 67%, about 65% to about 70%, about 68% to about 72%, about 70% to about 75%, about 72% to about 76%, about 75% to about 80%, about 77% to about 82%, about 80% to about 85%, about 82% to about 87%, about 85% to about 90%, about 87% to about 92%, or about 90% to about 95% w / w of the composition. In some embodiments, the solvent is present in an amount of about 76% to about 79% w / w of the composition. In some embodiments, the solvent is present in an amount of about 77% to about 78% w / w of the composition. In some embodiments, the solvent is present in an amount of about 72% to about 76% w / w of the composition. In some embodiments, the solvent is present in an amount of about 69% to about 71% w / w of the composition. In some embodiments, the solvent is present in an amount of about 70% to about 71% w / w of the composition. In some embodiments, the solvent is present in an amount of about 50%, about 55%, about 60%, about 65%, about 66%, about 67%, about 68%, about 69%, about 70%, about 71%, about 72%, about 73%, about 74%, about 75%, about 76%, about 77%, about 78%, about 79%, about 80%, about 85%, about 90%, or about 95% w / w of the composition. In some embodiments, the solvent is present in an amount of about 77% w / w of the composition. In some embodiments, the solvent is present in an amount of about 74% w / w of the composition. In some embodiments, the solvent is present in an amount of about 71% w / w of the composition.

[0064] In some embodiments, the solvent is a combination of two or more solvents, such as two or more of water, methanol, ethanol, isopropanol, and diethylene glycol monoethyl ether. In some embodiments, each solvent is independently present in an amount of about 5% to about 80% w / w of the composition. For example, each solvent can be independently present in an amount of about 5% to about 10%, about 5% to about 20%, about 5% to about 30%, about 5% to about 40%, about 5% to about 50%, about 5% to about 60%, about 5% to about 70%, about 70% to about 80%, about 60% to about 80%, about 50% to about 80%, about 40% to about 80%, about 30% to about 80%, about 20% to about 80%, or about 10% to about 80% w / w of the composition. In some embodiments, the solvent is present in an amount of about 15% to about 25%, about 20% to about 30%, about 25% to about 35%, about 30% to about 40%, about 35% to about 45%, about 40% to about 50%, about 45% to about 50%, or about 50% to about 60% w / w of the composition. For example, each solvent can be independently present in an amount of about 15%, about 16%, about 17%, about 18%, about 19%, about 20%, about 21%, about 22%, about 23%, about 24%, about 25%, about 26%, about 27%, about 28%, about 29%, about 30%, about 31%, about 32%, about 33%, about 34%, about 35%, about 36%, about 37%, about 38%, about 39%, about 40%, about 41%, about 42%, about 43%, about 44%, about 45%, about 46%, about 47%, about 48%, about 49%, about 50%, about 51%, about 52%, about 53%, about 54%, or about 55% w / w of the composition.

[0065] In some embodiments, the solvent is a combination of water and ethanol. In some embodiments, water is present in an amount of about 15% to about 40% w / w of the composition, and ethanol is present in an amount of about 30% to about 55% w / w of the composition. For example, water is present in an amount of about 20% to about 30%, about 25% to about 35%, about 25% to about 30%, or about 28% to about 32% w / w of the composition, and ethanol is present in an amount of about 35% to about 45%, about 40% to about 50%, about 40% to about 55%, about 45% to about 55%, about 45% to about 50%, about 40% to about 45%, about 42% to about 47%, or about 45% to about 50% w / w of the composition. In some embodiments, water is present in an amount of about 25% to about 30% w / w of the composition, and ethanol is present in an amount of about 40% to about 50% w / w of the composition. In some embodiments, water is present in an amount of about 28% to about 32% w / w of the composition, and ethanol is present in an amount of about 45% to about 50% w / w of the composition. In some embodiments, water is present in an amount of about 15% to about 25%, about 18% to about 22%, or about 19% to about 21% w / w of the composition, and ethanol is present in an amount of about 45% to about 55%, about 48% to about 52%, or about 49% to about 51% w / w of the composition. In some embodiments, water is present in an amount of about 15%, about 16%, about 17%, about 18%, about 19%, about 20%, about 21%, about 22%, about 23%, about 24%, about 25%, about 26%, about 27%, about 28%, about 29%, about 30%, about 31%, about 32%, about 33%, about 34%, or about 35% w / w of the composition, and ethanol is present in an amount of about 40%, about 41%, about 42%, about 43%, about 44%, about 45%, about 46%, about 47%, about 48%, about 49%, about 50%, about 51%, about 52%, about 53%, about 54%, or about 55% w / w of the composition. In some embodiments, water is present in an amount of about 28% w / w of the composition and ethanol is present in an amount of about 46% w / w of the composition. In some embodiments, water is present in an amount of about 30% w / w of the composition and ethanol is present in an amount of about 48% w / w of the composition. In some embodiments, water is present in an amount of about 21% w / w of the composition and ethanol is present in an amount of about 50% w / w of the composition.

[0066] As used herein, "thickener" refers to an agent that increases the viscosity of a liquid. In some embodiments, the thickener increases the viscosity of a liquid without substantially changing other properties of the liquid. Non-limiting examples of thickeners include starch, gums (e.g., natural and synthetic gums), cellulose, and arabinogalactan. Non-limiting examples of starches include starch aluminum octenyl succinate. Non-limiting examples of gums include xanthan gum, sclerotium gum, tragacanth gum, pectin, karaya gum, gum arabic, agar, guar gum, carrageenan, locust bean gum, alginate, arginine, gelatin, tara gum, ghatti gum, gellan gum, konjac gum, cassia gum, spruce gum, chicle gum, dammar, curdlan gum, and pullulan. Non-limiting examples of cellulosics include hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methylcellulose, ethyl cellulose, soybean hemicellulose, and sodium carboxymethyl cellulose.

[0067] In some embodiments, the thickening agent is present in an amount of about 0.01% to about 1% w / w of the composition, e.g., about 0.01% to about 0.05%, about 0.01% to about 0.1%, about 0.01% to about 0.15%, about 0.01% to about 0.2%, about 0.01% to about 0.3%, about 0.01% to about 0.4%, about 0.01% to about 0.5%, about 0.01% to about 0.6%, about 0.01% to about 0.7%, about 0.01% to about 0. In some embodiments, the thickener is present in an amount of about 0.05% to about 0.25%, about 0.05% to about 0.2%, about 0.1% to about 0.2%, or about 0.1% to about 0.15% w / w of the composition. In some embodiments, the thickener is present in an amount of about 0.05% to about 0.25%, about 0.05% to about 0.2%, about 0.1% to about 0.2%, or about 0.1% to about 0.15% w / w of the composition. In some embodiments, the thickener is present in an amount of about 0.05% to about 0.2% w / w of the composition. In some embodiments, the thickening agent is present in an amount of about 0.01%, about 0.05%, 0.06%, about 0.07%, about 0.08%, about 0.09%, about 0.10%, about 0.11%, about 0.12%, about 0.13%, about 0.14%, about 0.15%, about 0.16%, about 0.17%, about 0.18%, about 0.19%, about 0.2%, about 0.22%, about 0.24%, about 0.26%, about 0.28%, about 0.3%, about 0.4%, about 0.5%, about 0.6%, about 0.8%, about 0.9%, or about 1% w / w of the composition. In some embodiments, the thickening agent is present in an amount of about 0.12% w / w of the composition.

[0068] In some embodiments, the thickening agent is a combination of two or more thickening agents, such as arabinogalactan, aluminum starch octenylsuccinate, xanthan gum, sclerotium gum, tragacanth gum, pectin, karaya gum, gum arabic, agar, guar gum, carrageenan, locust bean gum, alginate, arginine, gelatin, tara gum, ghatti gum, gellan gum, konjac gum, cassia gum, spruce gum, chicle gum, dammar, curdlan gum, pullulan, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methylcellulose, ethyl cellulose, soybean hemicellulose, and sodium carboxymethyl cellulose. In some embodiments, each thickening agent is independently present in an amount of about 0.01% to about 0.5% w / w of the composition. For example, each thickener may be present in an amount of about 0.01% to about 0.05%, about 0.01% to about 0.1%, about 0.01% to about 0.15%, about 0.01% to about 0.2%, about 0.01% to about 0.25%, about 0.01% to about 0.3%, about 0.01% to about 0.35% w / w of the composition, about 0.01% to about 0.4%, about 0.01% to about 0.4% of the composition, about 0.01% to about 0.5% of the composition, about 0.01% to about 0.6% of the composition, about 0.01% to about 0.7% of the composition, about 0.01% to about 0.8% of the composition, about 0.01% to about 0.9% of the composition, about 0.01% to about 0.10% of the composition, about 0.01% to about 0.15% of the composition, about 0.01% to about 0.25%, about 0.01% to about 0.25%, about 0.01% to about 0.35% w / w of the composition, about 0.01% to about 0.4% of the composition, about 0.01% to about 0.5% of the composition, about 0.01% to about 0.6% of the composition, about 0.01% to about 0.7% of the composition, about 0.01% to about 0.8% of the composition, about 0.01% to about 0.9% of the composition, about 0.01% to about 0.15% of the composition, about 0.01% to about 0.25%, about 0.01% to about 0.35% w / w of the composition, about 0.01% to about 0.4 They may be present independently in an amount of about 0.45%, about 0.45% to about 0.5%, about 0.4% to about 0.5%, about 0.35% to about 0.5%, about 0.3% to about 0.5%, about 0.25% to about 0.5%, about 0.2% to about 0.5%, about 0.15% to about 0.5%, about 0.1% to about 0.15%, or about 0.05% to about 0.15% w / w. In some embodiments, each thickening agent is independently present in an amount of about 0.01% to about 0.04%, about 0.02% to about 0.06%, about 0.03% to about 0.07%, 0.04% to about 0.08%, about 0.06% to about 0.1%, or about 0.08% to about 0.12%, or about 0.1% to about 0.14% w / w of the composition.For example, each thickening agent may be independently present in an amount of about 0.01%, about 0.02%, about 0.03%, about 0.04%, about 0.05%, about 0.06%, about 0.07%, about 0.08%, about 0.09%, about 0.1%, about 0.11%, about 0.12%, about 0.13%, about 0.14%, about 0.15%, about 0.16%, about 0.17%, about 0.18%, about 0.19%, about 0.2%, about 0.22%, about 0.24%, about 0.26%, about 0.28%, about 0.3%, about 0.4%, about 0.5%, about 0.6%, about 0.8%, about 0.9%, or about 1% w / w of the composition.

[0069] In some embodiments, the thickening agent is a combination of hydroxyethyl cellulose and xanthan gum, in which the hydroxyethyl cellulose is present in an amount of about 0.01% to about 0.5% w / w of the composition, and the xanthan gum is present in an amount of about 0.01% to about 0.5% w / w of the composition. In some embodiments, the hydroxyethyl cellulose is present in an amount of about 0.01% to about 0.04%, about 0.02% to about 0.06%, about 0.03% to about 0.07%, about 0.04% to about 0.08%, about 0.06% to about 0.1%, about 0.08% to about 0.12%, or about 0.1% to about 0.14% w / w of the composition, and the xanthan gum is present in an amount of about 0.01% to about 0.04%, about 0.02% to about 0.06%, about 0.03% to about 0.07%, 0.04% to about 0.08%, about 0.06% to about 0.1%, about 0.08% to about 0.12%, or about 0.1% to about 0.14% w / w of the composition. In some embodiments, the hydroxyethyl cellulose is present in an amount of about 0.04% to about 0.08% w / w of the composition, and the xanthan gum is present in an amount of about 0.04% to about 0.08% w / w of the composition. In some embodiments, the hydroxyethyl cellulose is present in an amount of about 0.01%, about 0.02%, about 0.03%, about 0.04%, about 0.05%, about 0.06%, about 0.07%, about 0.08%, about 0.09%, about 0.1%, about 0.11%, about 0.12%, about 0.13%, about 0.14%, about 0.15%, about 0.16%, about 0.17%, about 0.18%, about 0.19%, or about 0.2% w / w of the composition. In some embodiments, the hydroxyethyl cellulose is present in an amount of about 0.06% w / w of the composition, and the xanthan gum is present in an amount of about 0.01%, about 0.02%, about 0.03%, about 0.04%, about 0.05%, about 0.06%, about 0.07%, about 0.08%, about 0.09%, about 0.1%, about 0.11%, about 0.12%, about 0.13%, about 0.14%, about 0.15%, about 0.16%, about 0.17%, about 0.18%, about 0.19%, or about 0.2% w / w of the composition. In some embodiments, the hydroxyethyl cellulose is present in an amount of about 0.06% w / w of the composition, and the xanthan gum is present in an amount of about 0.06% w / w of the composition.

[0070] As used herein, "humectant" refers to a substance that attracts water. For example, a humectant can attract water and provide moisture to the skin. Non-limiting examples of humectants include polyhydric alcohols, such as polyalkylene glycols (e.g., alkylene polyols and their derivatives), alphahydroxy acids, sugars, aloe vera gel, lithium chloride, allantoin, urea, and dicyanamide. Non-limiting examples of polyhydric alcohols include glycerol, lactic acid, propylene glycol, propanediol, polyethylene glycol, dipropylene glycol, polypropylene glycol, polyethylene glycol and its derivatives, hexylene glycol, 1,3-butylene glycol, 1,2,6-hexanetriol, ethoxylated glycerol, propoxylated glycerol, glyceryl triacetate, sorbitol, hydroxypropyl sorbitol, xylitol, maltitol, hyaluronic acid, tremella extract, sodium lactate, sodium urea L-pyroglutamate, and pyrrolidone carboxylic acid.

[0071] In some embodiments, the humectant is present in an amount of about 0.1% to about 20% w / w of the composition (e.g., about 0.1% to about 1%, about 0.1% to about 5%, about 0.1% to about 10%, about 0.1% to about 15%, about 15% to about 20%, about 10% to about 20%, about 5% to about 20%, or about 1% to about 20% w / w of the composition). In some embodiments, the humectant is present in an amount of about 0.5% to about 2%, about 0.5% to about 5%, about 1% to about 10%, about 1% to about 5%, about 2% to about 7%, about 5% to about 10%, about 7% to about 12%, or about 10% to about 15% w / w of the composition. In some embodiments, the humectant is present in an amount of about 0.5% to about 1.5% w / w of the composition. In some embodiments, the humectant is present in an amount of about 2% to about 6% w / w of the composition. In some embodiments, the humectant is present in an amount of about 0.1%, about 0.5%, about 1%, about 1.5%, about 2%, about 2.5%, about 3%, about 3.5%, about 4%, about 4.5%, about 5%, about 5.5%, about 6%, about 6.5%, about 7%, about 7.5%, about 8%, about 8.5%, about 9%, about 9.5%, about 10%, about 11%, about 12%, about 13%, about 14%, about 15%, about 16%, about 17%, about 18%, about 19%, or about 20% w / w of the composition. In some embodiments, the humectant is present in an amount of about 4% w / w of the composition. In some embodiments, the humectant is present in an amount of about 1% w / w of the composition.

[0072] In some embodiments, the humectant is propanediol. In some embodiments, the propanediol is present in an amount of about 0.1% to about 20% w / w of the composition. For example, about 0.1% to about 1%, about 0.1% to about 5%, about 0.1% to about 10%, about 0.1% to about 15%, about 15% to about 20%, about 10% to about 20%, about 5% to about 20%, or about 1% to about 20% w / w of the composition. In some embodiments, the propanediol is present in an amount of about 0.5% to about 2%, about 0.5% to about 5%, about 1% to about 10%, about 1% to about 5%, about 2% to about 7%, about 5% to about 10%, about 7% to about 12%, or about 10% to about 15% w / w of the composition. In some embodiments, the propanediol is present in an amount of about 0.5% to about 1.5% w / w of the composition. In some embodiments, the propanediol is present in an amount of about 2% to about 6% w / w of the composition. In some embodiments, the propanediol is present in an amount of about 0.1%, about 0.5%, about 1%, about 1.5%, about 2%, about 2.5%, about 3%, about 3.5%, about 4%, about 4.5%, about 5%, about 5.5%, about 6%, about 6.5%, about 7%, about 7.5%, about 8%, about 8.5%, about 9%, about 9.5%, about 10%, about 11%, about 12%, about 13%, about 14%, about 15%, about 16%, about 17%, about 18%, about 19%, or about 20% w / w of the composition. In some embodiments, the propanediol is present in an amount of about 4% w / w of the composition. In some embodiments, the propanediol is present in an amount of about 1% w / w of the composition.

[0073] In some embodiments, the humectant is glycerin. In some embodiments, glycerin is present in an amount of about 0.1% to about 20% w / w of the composition. For example, about 0.1% to about 1%, about 0.1% to about 5%, about 0.1% to about 10%, about 0.1% to about 15%, about 15% to about 20%, about 10% to about 20%, about 5% to about 20%, or about 1% to about 20% w / w of the composition. In some embodiments, glycerin is present in an amount of about 1% to about 10%, about 1% to about 5%, about 2% to about 7%, about 5% to about 10%, about 7% to about 12%, or about 10% to about 15% w / w of the composition. In some embodiments, glycerol is present in an amount of about 2% to about 6% w / w of the composition. In some embodiments, glycerol is present in an amount of about 1%, about 1.5%, about 2%, about 2.5%, about 3%, about 3.5%, about 4%, about 4.5%, about 5%, about 5.5%, about 6%, about 6.5%, about 7%, about 7.5%, about 8%, about 8.5%, about 9%, about 9.5%, about 10%, about 11%, about 12%, about 13%, about 14%, about 15%, about 16%, about 17%, about 18%, about 19%, or about 20% w / w of the composition. In some embodiments, glycerol is present in an amount of about 4% w / w of the composition.

[0074] As used herein, "film-forming agent" refers to a compound that can form a continuous film on the skin. In some embodiments, the film-forming agent is a compound that forms a continuous film on the skin when dry. Non-limiting examples of film-forming agents include volatile silicone resins, polyvinylpyrrolidone, acrylates, acrylamide copolymers, and isododecane resins. Non-limiting examples of volatile silicone resins include polymethylsilsesquioxane, trimethylsiloxysilicate, polypropylsilsesquioxane, dimethicone, cyclopentasiloxane, dimethiconol crosspolymer, polysilicone-6, polysilicone-8, polysilicone-11, and polysilicone-14. Non-limiting examples of copolymers include acrylate copolymer, styrene / acrylate copolymer, acrylate / C12-22 alkyl methacrylate copolymer, acrylate / polytrimethylsiloxymethacrylate copolymer, polyvinylpyrrolidone / vinyl acetate (VP / VA) copolymer, VP / dimethiconyl acrylate / polycarbamyl / polyglycol ester, VP / dimethylaminoethyl methacrylate copolymer, VP / dimethylaminoethyl methacrylate / polycarbamyl polyglycol ester, VP / eicosene copolymer, VP / hexadecene copolymer, VP / methacrylamide / vinylimidazole copolymer, VP / polycarbamyl polyglycol ester, VP / VA copolymer, polyester-1, polyester-2, polyester-3, polyester-4, polyester-5, polyester-7, polyester-8, and polyester-10.

[0075] In some embodiments, the film-forming agent is present in an amount of about 0.1% to about 20% w / w of the composition. For example, about 0.1% to about 1%, about 0.1% to about 5%, about 0.1% to about 10%, about 0.1% to about 15%, about 15% to about 20%, about 10% to about 20%, about 5% to about 20%, or about 1% to about 20% w / w of the composition. In some embodiments, the film-forming agent is present in an amount of about 1% to about 10%, about 1% to about 5%, about 2% to about 7%, about 5% to about 10%, about 7% to about 12%, or about 10% to about 15% w / w of the composition. In some embodiments, the film-forming agent is present in an amount of about 4% to about 6% w / w of the composition. In some embodiments, the film-forming agent is present in an amount of about 6% to about 9% w / w of the composition. In some embodiments, the film-forming agent is present in an amount of about 1%, about 1.5%, about 2%, about 2.5%, about 3%, about 3.5%, about 4%, about 4.5%, about 5%, about 5.5%, about 6%, about 6.5%, about 7%, about 7.5%, about 8%, about 8.5%, about 9%, about 9.5%, about 10%, about 11%, about 12%, about 13%, about 14%, about 15%, about 16%, about 17%, about 18%, about 19%, or about 20% w / w of the composition. In some embodiments, the film-forming agent is present in an amount of about 5% w / w of the composition. In some embodiments, the film-forming agent is present in an amount of about 7.5% w / w of the composition.

[0076] In some embodiments, the film former is a combination of two or more film formers, such as polymethylsilsesquioxane, trimethylsiloxysilicate, polypropylsilsesquioxane, dimethicone, cyclopentasiloxane, dimethiconol crosspolymer, polysilicone-6, polysilicone-8, polysilicone-11, polysilicone-14, acrylate copolymer, styrene / acrylate copolymer, polyvinylpyrrolidone, acrylate / C12-22 alkyl methacrylate copolymer, acrylate / polytrimethylsiloxymethacrylate copolymer, polyvinylpyrrolidone / vinyl acetate (VP / VA) copolymer, VP / acrylate copolymer, polyvinylpyrrolidone / vinyl acetate (VP / VA) ... Two or more of methiconyl / polycarbamyl / polyglycol ester, VP / dimethylaminoethyl methacrylate copolymer, VP / dimethylaminoethyl methacrylate / polycarbamyl polyglycol ester, VP / eicosene copolymer, VP / hexadecene copolymer, VP / methacrylamide / vinylimidazole copolymer, VP / polycarbamyl polyglycol ester, VP / VA copolymer, polyester-1, polyester-2, polyester-3, polyester-4, polyester-5, polyester-7, polyester-8, and polyester-10. In some embodiments, each film-forming agent is independently present in an amount of about 0.1% to about 15% w / w of the composition, e.g., about 0.1% to about 1%, about 0.1% to about 5%, about 0.1% to about 10%, about 10% to about 15%, about 5% to about 15%, or about 1% to about 15% w / w of the composition. In some embodiments, each film-forming agent is present in an amount of about 0.1% to about 2%, about 0.5% to about 2%, about 1% to about 10%, about 1% to about 5%, about 2% to about 7%, about 5% to about 10%, about 7% to about 12%, or about 10% to about 15% w / w of the composition. For example, about 0.1%, about 0.25%, about 0.5%, about 0.75%, about 1%, about 1.5%, about 2%, about 2.5%, about 3%, about 3.5%, about 4%, about 4.5%, about 5%, about 5.5%, about 6%, about 6.5%, about 7%, about 7.5%, about 8%, about 8.5%, about 9%, about 9.5%, about 10%, about 11%, about 12%, about 13%, about 14%, about 15%, about 16%, about 17%, about 18%, about 19%, or about 20% w / w of the composition.

[0077] In some embodiments, the film-forming agent is a combination of polymethylsilsesquioxane and an acrylate / C12-22 alkyl methacrylate copolymer, in which the polymethylsilsesquioxane is present in an amount of about 0.5% to about 10% w / w of the composition, and the acrylate / C12-22 alkyl methacrylate copolymer is present in an amount of about 0.5% to about 10% w / w of the composition. For example, the polymethylsilsesquioxane is present in an amount of about 0.05% to about 1%, about 0.05% to about 5%, about 0.05% to about 8%, about 8% to about 10%, about 5% to about 10%, about 1% to about 10%, or about 1% to about 5% w / w of the composition, and the acrylates / C12-22 alkyl methacrylate copolymer is present in an amount of about 0.05% to about 1%, about 0.05% to about 5%, about 0.05% to about 8%, about 8% to about 10%, about 5% to about 10%, about 1% to about 10%, or about 1% to about 5% w / w of the composition. In some embodiments, the polymethylsilsesquioxane is present in an amount of about 1% to about 5% w / w of the composition, and the acrylates / C12-22 alkyl methacrylate copolymer is present in an amount of about 1% to about 5% w / w of the composition. In some embodiments, the polymethylsilsesquioxane is present in an amount of about 0.5%, about 1%, about 1.5%, about 2%, about 2.5%, about 3%, about 3.5%, about 4%, about 4.5%, about 5%, about 5.5%, about 6%, about 6.5%, about 7%, about 7.5%, about 8%, about 8.5%, about 9%, about 9.5%, or about 10% w / w of the composition, The acrylate / C12-22 alkyl methacrylate copolymer is present in an amount of about 0.5%, about 1%, about 1.5%, about 2%, about 2.5%, about 3%, about 3.5%, about 4%, about 4.5%, about 5%, about 5.5%, about 6%, about 6.5%, about 7%, about 7.5%, about 8%, about 8.5%, about 9%, about 9.5%, or about 10% w / w of the composition. In some embodiments, the polymethylsilsesquioxane is present in an amount of about 2% w / w of the composition and the acrylate / C12-22 alkyl methacrylate copolymer is present in an amount of about 3% w / w of the composition.

[0078] In some embodiments, the film-forming agent is a combination of an acrylate copolymer, polyvinylpyrrolidone, and a styrene / acrylate copolymer, in which the acrylate copolymer is present in an amount of about 0.1% to about 10% w / w of the composition, the polyvinylpyrrolidone is present in an amount of about 0.1% to about 10% w / w of the composition, and the styrene / acrylate copolymer is present in an amount of about 0.1% to about 10% w / w of the composition. In some embodiments, the acrylate copolymer is present in an amount of about 0.1% to about 1%, about 0.1% to about 5%, about 0.1% to about 8%, about 8% to about 10%, about 5% to about 10%, or about 1% to about 10% w / w of the composition; the polyvinylpyrrolidone is present in an amount of about 0.1% to about 1%, about 0.1% to about 5%, about 0.1% to about 8%, about 8% to about 10%, about 5% to about 10%, or about 1% to about 10% w / w of the composition; and the styrene / acrylate copolymer is present in an amount of about 0.1% to about 1%, about 0.1% to about 5%, about 0.1% to about 8%, about 8% to about 10%, about 5% to about 10%, or about 1% to about 10% w / w of the composition. In some embodiments, the acrylate copolymer is present in an amount of about 0.1% to about 1% w / w of the composition, the polyvinylpyrrolidone is present in an amount of about 0.5% to about 1.5% w / w of the composition, and the styrene / acrylate copolymer is present in an amount of about 5% to about 7% w / w of the composition. In some embodiments, the acrylate copolymer is present in an amount of about 0.1%, about 0.25%, about 0.5%, about 1%, about 1.5%, about 2%, about 2.5%, about 3%, about 3.5%, about 4%, about 4.5%, or about 5% w / w of the composition, and the polyvinylpyrrolidone is present in an amount of about 0.25%, about 0.5%, about 1%, about 1.5%, about 2%, about 2.5%, about 3%, about 3.5%, or about 5% w / w of the composition. The styrene / acrylate copolymer is present in an amount of about 1%, about 1.5%, about 2%, about 2.5%, about 3%, about 3.5%, about 4%, about 4.5%, about 5%, about 5.5%, about 6%, about 6.5%, about 7%, about 7.5%, about 8%, about 8.5%, about 9%, about 9.5%, or about 10% w / w of the composition.In some embodiments, the acrylate copolymer is present in an amount of about 0.25% w / w of the composition, the polyvinylpyrrolidone is present in an amount of about 1% w / w of the composition, and the styrene / acrylate copolymer is present in an amount of about 6% w / w of the composition.

[0079] In some embodiments, the ink composition can further comprise a preservative. As used herein, "preservative" refers to an agent that protects against decay, discoloration, and / or spoilage. Non-limiting examples of preservatives include ascorbic acid, ascorbate, palmitate, citric acid, benzoate, benzoic acid, propionate, propionic acid, sorbate, sorbic acid, salicylic acid, salicylate, hexa-2,4-dienoic acid, hexa-2,4-dienoate, formaldehyde, formaldehyde-releasing agents, formic acid and its salts, 3-acetyl-6-methylpyran-2,4-(3H)-dione and its salts, 3,3'-dibromo-4,4'-hexamethylenedioxydibenzamidine and its salts, thiomersal, phenylmercury salts, undec-10-enoic acid and its salts, 1,3-bis(2-ethylhexyl)hexahydroxybenzoate, methylparaben ... 5-methyl-5-pyrimidine, 5-bromo-5-nitro-1,3-dioxane, bronopol, 2,4-dichlorobenzyl alcohol, 1-(4-chlorophenyl)-3-(3,4-dichlorophenyl)urea, chlorocresol, chloroxylenol, 5-chloro-2-(2,4-dichlorophenoxy)phenol, N,N'-methylenebis[N'-[3-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]urea], polyaminopropyl biguanide, methenamine, quaternium-15, climbazole, DMDM ​​hydantoin, benzyl alcohol, 1-hydroxy-4-methyl-6-(2,4,4-Trimethylpentyl)-2-pyridone, Piroctone Olamine, Bromochlorophene, o-Cymen-5-ol, Chlorphen, Chloroacetamine, Methylchloroisothiazolinone, Methylisothiazolinone, Phenoxyisopropanol, Chlorhexidine, Chlorhexidine Diacetate, Chlorhexidine Digluconate, Chlorhexidine Dihydrochloride, Dimethyloxazolidine, Behentrimonium Chloride, Cetrimonium Bromide, Cetrimonium Chloride, Lautrimonium Bromide, Lautrimonium Chloride, Steartrimonium Bromide, Steartrimonium Chloride, Diazolidinyl Urea, Hexamidine, Hexamidine Diisethionate, Hexamidine Paraben, Glutaral, 7-Ethylbicyclooxazolidine, Chlorphenesin, Hydroxymethylglycinate Sodium, silver chloride, benzethonium chloride, benzalkonium chloride, benzalkonium bromide, benzalkonium saccharinate, benzyl hemiformal, iodopropynyl butylcarbamate, biphenyl-2-ol and its salts, zinc pyrithione, erythorbate, nitrous acid, ethylenediaminetetraacetic acid (EDTA), butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), caprylic acid, dilauryl thiodipropionate, erythorbic acid, guaiac butter, methylparaben, sulfite, bisulfite, metabisulfite, propylparaben, stannous chloride, sulfur dioxide, thiodipropionic acid, isothiazolinone, parabens, phenoxyethanol, ethylhexylglycerin, glycol, and tocopherol.

[0080] In some embodiments, the preservative is present in an amount of about 0.05% to about 10% w / w of the composition. For example, it may be about 0.05% to about 0.1%, about 0.05% to about 0.5%, about 0.05% to about 1%, about 0.05% to about 2%, about 0.05% to about 3%, about 0.05% to about 4%, about 0.05% to about 5%, about 0.05% to about 6%, about 0.05% to about 7%, about 0.05% to about 8%, about 0.05% to about 9%, about 9% to about 10%, about 8% to about 10%, about 7% to about 10%, about 6% to about 10%, about 5% to about 10%, about 4% to about 10%, about 3% to about 10%, about 2% to about 10%, about 1% to about 10%, about 0.5% to about 10%, or about 0.1% to about 10% w / w of the composition. In some embodiments, the preservative is present in an amount of about 1% to about 5% w / w of the composition. In some embodiments, the preservative is present in an amount of 0.1% to about 2%, 0.5% to about 2.5%, about 1% to about 3%, about 1.5% to about 3.5%, about 2% to about 4%, about 2.5% to about 4.5%, or about 3% to about 5% w / w of the composition. In some embodiments, the preservative is present in an amount of about 0.5% to about 1.5%, about 0.5% to about 1.0%, about 1.5% to about 2%, about 1% to about 2%, about 0.5% to about 2%, or about 0.8% to about 2% w / w of the composition. For example, about 0.05% to about 0.4%, about 0.05% to about 0.2%, about 0.2% to about 0.5%, about 0.15% to about 0.25%, or about 0.1% to about 0.3% w / w of the composition. In some embodiments, the preservative is present in an amount of about 0.01%, about 0.05%, about 0.1%, about 0.5%, about 1%, about 1.5%, about 2%, about 2.5%, about 3%, about 3.5%, about 4%, about 4.5%, about 5%, about 5.5%, or about 6% w / w of the composition. In some embodiments, the preservative is present in an amount of about 3% w / w of the composition. In some embodiments, the preservative is present in an amount of about 1% w / w of the composition.

[0081] In some embodiments, the preservative is a combination of two or more preservatives, such as two or more of ascorbic acid, ascorbate, palmitate, citric acid, benzoate, benzoic acid, propionate, propionic acid, sorbate, sorbic acid, salicylic acid, salicylate, hexa-2,4-dienoic acid, hexa-2,4-dienoate, formaldehyde, formaldehyde-releasing agents, formic acid and its salts, 3-acetyl-6-methylpyran-2,4-(3H)-dione and its salts, 3,3'-dibromo-4,4'-hexamethylenedioxydibenzamidine and its salts, thiomersal, phenylmercury salts, undecanoic acid, methyl ... Carboxylic acid and its salts, 1,3-bis(2-ethylhexyl)hexahydro-5-methyl-5-pyrimidine, 5-bromo-5-nitro-1,3-dioxane, bronopol, 2,4-dichlorobenzyl alcohol, 1-(4-chlorophenyl)-3-(3,4-dichlorophenyl)urea, chlorocresol, chloroxylenol, 5-chloro-2-(2,4-dichlorophenoxy)phenol, N,N'-methylenebis[N'-[3-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]urea], polyaminopropane Lopirbiguanide, methenamine, quaternium-15, climbazole, DMDM ​​hydantoin, benzyl alcohol, 1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2-pyridone, piroctone olamine, bromochlorophene, o-cymen-5-ol, chlorophene, chloroacetamine, methylchloroisothiazolinone, methylisothiazolinone, phenoxyisopropanol, chlorhexidine, chlorhexidine diacetate, chlorhexidine digluconate, chlorhexidine dichloride Benzyl alcohol, dimethyl oxazolidine, behentrimonium chloride, cetrimonium bromide, cetrimonium chloride, lauttrimonium bromide, lauttrimonium chloride, steartrimonium bromide, steartrimonium chloride, diazolidinyl urea, hexamidine, hexamidine diisethionate, hexamidine paraben, glutaral, 7-ethylbicyclooxazolidine, chlorphenesin, sodium hydroxymethylglycine, silver chloride, benzethonium chloride, benzalkonium chloride, benzalkonium bromide, benzalkonium saccharinate,benzyl hemiformal, iodopropynyl butylcarbamate, biphenyl-2-ol and its salts, zinc pyrithione, erythorbate, nitrous acid, ethylenediaminetetraacetic acid (EDTA), sodium lignosulfonate, butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), caprylic acid, dilauryl thiodipropionate, erythorbic acid, guaiac butter, methylparaben, sulfite, bisulfite, metabisulfite, propyl gallate, propylparaben, stannous chloride, sulfur dioxide, thiodipropionic acid, isothiazolinone, parabens, phenoxyethanol, ethylhexylglycerin, glycol, and tocopherol. In some embodiments, each preservative is independently present in an amount of about 0.01% to about 8% w / w of the composition. For example, about 0.01% to about 0.05%, about 0.01% to about 0.1%, about 0.01% to about 0.5%, about 0.01% to about 1%, about 0.01% to about 2%, about 0.01% to about 3%, about 0.01% to about 4%, about 0.01% to about 5%, about 0.01% to about 6%, about 0.01% to about 7%, about 7% to about 8%, about 6% to about 8%, about 5% to about 8%, about 4% to about 8%, about 3% to about 8%, about 2% to about 8%, about 1% to about 8%, about 0.5% to about 8%, or about 0.1% to about 8% w / w of the composition. In some embodiments, each preservative is independently present in an amount of about 0.05% to about 8% w / w of the composition. For example, about 0.05% to about 0.1%, about 0.05% to about 0.5%, about 0.05% to about 1%, about 0.05% to about 2%, about 0.05% to about 3%, about 0.05% to about 4%, about 0.05% to about 5%, about 0.05% to about 6%, about 0.05% to about 7%, about 7% to about 8%, about 6% to about 8%, about 5% to about 8%, about 4% to about 8%, about 3% to about 8%, about 2% to about 8%, about 1% to about 8%, about 0.5% to about 8%, or about 0.1% to about 8% w / w of the composition. In some embodiments, each preservative is independently present in an amount of about 1% to about 5% w / w of the composition. In some embodiments, each preservative is independently present in an amount of about 0.025% to about 0.1%, about 0.1% to about 2%, 0.5% to about 2.5%, about 1% to about 3%, about 1.5% to about 3.5%, about 2% to about 4%, about 2.5% to about 4.5%, or about 3% to about 5% w / w of the composition. In some embodiments, each preservative is present in an amount of about 0.5% to about 1.5%, about 1% to about 2%, about 2% to about 4.5%, or about 3% to about 5% w / w of the composition.Each preservative is independently present in an amount of about 0.5% to about 1.0%, about 1.5% to about 2%, about 1% to about 2%, about 0.5% to about 2%, or about 0.8% to about 2% w / w. In some embodiments, each preservative is independently present in an amount of about 0.01%, about 0.05%, about 0.1%, about 0.5%, about 1%, about 1.5%, about 2%, about 2.5%, about 3%, about 3.5%, about 4%, about 4.5%, about 5%, about 5.5%, or about 6% w / w of the composition.

[0082] In some embodiments, the preservative includes a combination of phenoxyethanol and ethylhexylglycerin. In some embodiments, the preservative further includes 1,2-hexanediol (e.g., the preservative is a combination of phenoxyethanol, ethylhexylglycerin, and 1,2-hexanediol). In some embodiments, the preservative further includes EDTA (e.g., the preservative is a combination of phenoxyethanol, ethylhexylglycerin, and EDTA). In some embodiments, the phenoxyethanol is present in an amount of about 0.1% to 5% w / w of the composition, the ethylhexylglycerin is present in an amount of about 0.01% to about 3% w / w of the composition, and the 1,2-hexanediol is present in an amount of about 0.1% to about 5% w / w of the composition. In some embodiments, phenoxyethanol is from about 0.1% to about 0.5%, from about 0.1% to about 1%, from about 0.1% to about 2%, from about 0.1% to about 3%, from about 0.1% to about 4%, from about 4% to about 5%, from about 3% to about 5%, from about 2% to about 5%, from about 1% to about 5%, from about 0.5% to about 5%, from about 0.5% to about 1%, or from about 0.5% to about 1% of the composition. and ethylhexylglycerin is present in an amount of about 0.01% to about 0.1%, 0.01% to about 0.5%, 0.01% to about 1%, about 0.01% to about 2%, about 2% to about 3%, about 1% to about 3%, or about 2.5% to about 4.5% w / w of the composition. and 1,2-hexanediol is present in an amount of about 0.1% to about 3%, about 0.05% to about 3%, about 0.05% to about 0.15%, about 0.05% to about 1%, 0.5% to about 2.5%, about 1% to about 3%, about 1.5% to about 3.5%, about 2% to about 4%, about 2.5% to about 4.5%, or about 3% to about 5% w / w of the composition. about 1%, about 0.1% to about 2%, about 0.1% to about 3%, about 0.1% to about 4%, about 4% to about 5%, about 3% to about 5%, about 2% to about 5%, about 1% to about 5%, 0.5% to about 2.5%, about 1% to about 3%, about 1.5% to about 3.5%, about 2% to about 4%, about 2.5% to about 4.5%, or about 3% to about 5% w / w.In some embodiments, phenoxyethanol is present in an amount of about 0.5%, about 0.6%, about 0.7%, about 0.8%, about 0.9%, about 1%, about 1.1%, about 1.2%, about 1.3%, about 1.4%, about 1.5%, about 2%, about 2.5%, about 3%, about 3.5%, about 4%, or about 4.5% w / w of the composition, and ethylhexylglycerin is present in an amount of about 0.01%, about 0.05%, about 0.06%, about 0.07%, about The 1,2-hexanediol is present in an amount of about 0.5%, about 1%, about 1.5%, about 2%, about 2.5%, about 3%, about 3.5%, about 4%, about 4.5%, about 5%, about 5.5%, or about 6% w / w of the composition.

[0083] In some embodiments, the preservative further comprises EDTA (e.g., the preservative is a combination of phenoxyethanol, ethylhexylglycerin, and EDTA). In some embodiments, the phenoxyethanol is present in an amount of about 0.1% to 5% w / w of the composition, the ethylhexylglycerin is present in an amount of about 0.01% to about 3% w / w of the composition, and the EDTA is present in an amount of about 0.01% to about 2% w / w of the composition. In some embodiments, phenoxyethanol is present in an amount of about 0.1% to about 0.5%, about 0.1% to about 1%, about 0.1% to about 2%, about 0.1% to about 3%, about 0.1% to about 4%, about 4% to about 5%, about 3% to about 5%, about 2% to about 5%, about 1% to about 5%, about 0.5% to about 5%, about 0.5% to about 1%, about 0.5% to about 2.5%, about 1% to about 3%, about 1.5% to about 3.5%, about 2% to about 4%, or about 2.5% to about 4.5% w / w of the composition, and ethylhexylglycerin is present in an amount of about 0.01% to about 0.1%, 0.01% to about 0.5%, 0.01% to about 1%, about 0.01% to about 2%, or about 2% w / w of the composition. about 1% to about 3%, about 1% to about 3%, about 0.1% to about 3%, about 0.05% to about 3%, about 0.05% to about 0.15%, about 0.05% to about 1%, 0.5% to about 2.5%, about 1% to about 3%, about 1.5% to about 3.5%, about 2% to about 4%, about 2.5% to about 4.5%, or about 3% to about 5% w / w, The TA is present in an amount of about 0.01% to about 0.05%, about 0.01% to about 0.1%, about 0.01% to about 0.5%, about 0.01% to about 1%, about 0.1% to about 1.5%, about 1.5% to about 2%, about 1% to about 2%, about 0.5% to about 2%, 0.1% to about 2%, or about 0.05% to about 2% w / w of the composition.In some embodiments, phenoxyethanol is present in an amount of about 0.5%, about 0.6%, about 0.7%, about 0.8%, about 0.9%, about 1%, about 1.1%, about 1.2%, about 1.3%, about 1.4%, about 1.5%, about 2%, about 2.5%, about 3%, about 3.5%, about 4%, or about 4.5% w / w of the composition, and ethylhexylglycerin is present in an amount of about 0.01%, about 0.05%, about The EDTA is present in an amount of about 0.01%, about 0.05%, about 0.1%, about 0.5%, about 1%, about 1.5%, or about 2% w / w of the composition.

[0084] In some embodiments, the phenoxyethanol and ethylhexylglycerin are present in the composition in a ratio of about 9:1 phenoxyethanol:ethylhexylglycerin (e.g., EUXYL® PE9010).

[0085] In some embodiments, the EDTA is disodium EDTA.

[0086] In some embodiments, the preservative further comprises sodium lignosulfonate.

[0087] In some embodiments, the ink composition may further comprise one or more temporary colorants. In some embodiments, the one or more temporary colorants are present in an amount of about 0.1% to about 10% w / w of the composition. For example, about 0.1% to about 1%, about 0.1% to about 5%, about 0.1% to about 8%, about 8% to about 10%, about 5% to about 10%, or about 1% to about 10% w / w of the composition. In some embodiments, the one or more temporary colorants are present in an amount of about 2% to about 3% w / w of the composition. In some embodiments, the one or more temporary colorants are present in an amount of about 2.5% w / w of the composition.In some embodiments, the one or more temporary colorants are iron oxide black (Fe3O4), iron oxide (FeO), carbon, logwood, ochre, cinnabar (HgS), cadmium red (CdSe), iron(III) oxide (Fe2O3), naphthol-AS pigment, disazodiarylide, disazopyrazolone, cadmium selenosulfide, cadmium yellow (CdS, CdZnS), curcuma yellow, chrome yellow (PbCrO4), disazodiarylide, chromium oxide (Cr2O3), malachite [Cu2(CO3)(OH)] 2], Ferrocyanide, Ferricyanide, Lead Chromate, Monoazo Pigments, Cu / Al Phthalocyanine, Cu Phthalocyanine, Azure Blue, Cobalt Blue, Cu-Phthalocyanine, Manganese Violet (Manganese Ammonium Pyrophosphate), Aluminum Salts, Quinacridone, Dioxazine / Carbazole, White Lead (Lead Carbonate), Titanium Dioxide (TiO2), Barium Sulfate (BaSO4), Zinc Oxide, Anthraquinone Dyes and Derivatives, Annatto, Caramel, β-Carotene, Bismuth Citrate, Copper Disodium EDTA Thorium, Copper Sodium Copper Chlorophyllin Potassium, Dihydroxyacetone, Bismuth Oxychloride, Guaiazulene, Henna, Iron Ammonium Ferrocyanide, Iron Ferrocyanide, Chromium Hydroxide Green, Chromium Oxide Green, Guanine, Lead Acetate, Pyrophyllite, Mica, Silver, Titanium Dioxide, Aluminum Powder, Bronze Powder, Copper Powder, Ultramarine, Manganese Violet, Zinc Oxide, Luminescent Zinc Sulfide, D&C Black No. 2 and No. 3, FD&C Blue No. 1 (e.g., Acid Blue 9), D&C Blue In some embodiments, the temporary colorant is selected from the group consisting of D&C Blue No. 4, D&C Brown No. 1, FD&C Green No. 3, D&C Green Nos. 5, 6, and 8, D&C Orange Nos. 4, 5, 10, and 11, FD&C Red No. 4, D&C Red Nos. 6, 7, 17, 21, 22, 27, 28, 30, 32, 33, 34, 36, and 40, D&C Violet No. 2, Ext. D&C Violet No. 2, FD&C Yellow Nos. 5 and 6, D&C Yellow Nos. 7, 8, 10, and 11, and Ext. D&C Yellow No. 7. In some embodiments, the temporary colorant does not contain an amine group. In some embodiments, the temporary colorant is D&C Black No. 2.

[0088] In some embodiments, the compositions provided herein comprise: genipin present in an amount of about 10% to about 20% w / w of the composition; a solvent present in an amount of about 65% to about 80% w / w of the composition; and a thickening agent present in an amount of about 0.01% to about 0.3% w / w of the composition. In some embodiments, the solvent is a combination of water and ethanol. In some such embodiments, the water is present in an amount of about 25% to about 30% w / w of the composition, and the ethanol is present in an amount of about 40% to about 50% w / w of the composition. In some embodiments, the thickening agent is a combination of hydroxyethyl cellulose and xanthan gum. In some such embodiments, the hydroxyethyl cellulose is present in an amount of about 0.01% to about 0.1% w / w of the composition, and the xanthan gum is present in an amount of about 0.01% to about 0.1% w / w of the composition.

[0089] In some embodiments, the composition further comprises a humectant present in an amount of about 1% to about 10% w / w of the composition, hi some embodiments, the humectant is glycerol.

[0090] In some embodiments, the composition further comprises a film-forming agent present in an amount of about 0.1% to about 10% w / w of the composition. In some embodiments, the film-forming agent is a combination of polymethylsilsesquioxane and an acrylate / C12-22 alkyl methacrylate copolymer. In some such embodiments, the polymethylsilsesquioxane is present in an amount of about 1% to about 5% w / w of the composition, and the acrylate / C12-22 alkyl methacrylate copolymer is present in an amount of about 1% to about 5% w / w of the composition.

[0091] In some embodiments, the composition further comprises a humectant present in an amount of about 0.1% to about 5% w / w of the composition. In some embodiments, the preservative includes a combination of phenoxyethanol and ethylhexylglycerin. In some embodiments, the preservative includes a combination of phenoxyethanol, ethylhexylglycerin, and 1,2-hexanediol. In some such embodiments, the phenoxyethanol and ethylhexylglycerin are both present in the composition in an amount of about 0.1% to about 2% w / w of the composition. In some such embodiments, the phenoxyethanol and ethylhexylglycerin are present in the composition in a ratio of about 9:1 phenoxyethanol:ethylhexylglycerin. In some such embodiments, the 1,2-hexanediol is present in an amount of about 1% to about 3% w / w of the composition.

[0092] In some embodiments, the compositions provided herein comprise: genipin present in an amount of about 10% to about 20% w / w of the composition; a solvent present in an amount of about 65% to about 80% w / w of the composition; and a humectant present in an amount of about 1% to about 10% w / w of the composition. In some embodiments, the solvent is a combination of water and ethanol. In some embodiments, water is present in an amount of about 25% to about 30% w / w of the composition. In some such embodiments, ethanol is present in an amount of about 40% to about 50% w / w of the composition. In some embodiments, the humectant is glycerol.

[0093] In some embodiments, the composition further comprises a thickening agent present in an amount of about 0.01% to about 0.3% w / w of the composition. In some embodiments, the thickening agent is a combination of hydroxyethyl cellulose and xanthan gum. In some such embodiments, the hydroxyethyl cellulose is present in an amount of about 0.01% to about 0.1% w / w of the composition, and the xanthan gum is present in an amount of about 0.01% to about 0.1% w / w of the composition.

[0094] In some embodiments, the composition further comprises a film-forming agent present in an amount of about 0.1% to about 10% w / w of the composition. In some embodiments, the film-forming agent is a combination of polymethylsilsesquioxane and acrylates / C12-22 alkyl methacrylate copolymer. In some such embodiments, the polymethylsilsesquioxane is present in an amount of about 1% to about 5% w / w of the composition, and the acrylates / C12-22 alkyl methacrylate copolymer is present in an amount of about 1% to about 5% w / w of the composition. In some embodiments, the composition further comprises a humectant present in an amount of about 1% to about 10% w / w of the composition. In some embodiments, the humectant is glycerol.

[0095] In some embodiments, the composition further comprises a humectant present in an amount of about 0.1% to about 5% w / w of the composition. In some embodiments, the preservative includes a combination of phenoxyethanol and ethylhexylglycerin. In some embodiments, the preservative includes a combination of phenoxyethanol, ethylhexylglycerin, and 1,2-hexanediol. In some such embodiments, the phenoxyethanol and ethylhexylglycerin are both present in the composition in an amount of about 0.1% to about 2% w / w of the composition. In some such embodiments, the phenoxyethanol and ethylhexylglycerin are present in the composition in a ratio of about 9:1 phenoxyethanol:ethylhexylglycerin. In some such embodiments, the 1,2-hexanediol is present in an amount of about 1% to about 3% w / w of the composition.

[0096] In some embodiments, the compositions provided herein comprise: genipin present in an amount of about 12% to about 16% w / w of the composition; a solvent present in an amount of about 72% to about 76% w / w of the composition; and a thickening agent present in an amount of about 0.05% to about 0.20% w / w of the composition. In some embodiments, the solvent is a combination of water and ethanol. In some such embodiments, the water is present in an amount of about 25% to about 30% w / w of the composition, and the ethanol is present in an amount of about 45% to about 47% w / w of the composition. In some embodiments, the thickening agent is a combination of hydroxyethyl cellulose and xanthan gum. In some such embodiments, the hydroxyethyl cellulose is present in an amount of about 0.04% to about 0.08% w / w of the composition, and the xanthan gum is present in an amount of about 0.04% to about 0.08% w / w of the composition.

[0097] In some embodiments, the composition further comprises a film-forming agent present in an amount of about 4% to about 6% w / w of the composition. In some embodiments, the film-forming agent is a combination of polymethylsilsesquioxane and an acrylate / C12-22 alkyl methacrylate copolymer. In some such embodiments, the polymethylsilsesquioxane is present in an amount of about 1% to about 5% w / w of the composition, and the acrylate / C12-22 alkyl methacrylate copolymer is present in an amount of about 1% to about 5% w / w of the composition.

[0098] In some embodiments, the composition further comprises a humectant present in an amount of about 2% to about 6% w / w of the composition, hi some embodiments, the humectant is glycerol.

[0099] In some embodiments, the composition further comprises a preservative present in an amount of 2% to about 4% w / w of the composition. In some embodiments, the preservative includes a combination of phenoxyethanol and ethylhexylglycerin. In some embodiments, the preservative includes a combination of phenoxyethanol, ethylhexylglycerin, and 1,2-hexanediol. In some such embodiments, the phenoxyethanol and ethylhexylglycerin are both present in the composition in an amount of about 0.1% to about 2% w / w of the composition. In some such embodiments, the phenoxyethanol and ethylhexylglycerin are present in the composition in a ratio of about 9:1 phenoxyethanol:ethylhexylglycerin. In some such embodiments, the 1,2-hexanediol is present in an amount of about 1% to about 3% w / w of the composition.

[0100] In some embodiments, the compositions provided herein comprise: genipin present in an amount of about 12% to about 16% w / w of the composition; a solvent present in an amount of about 72% to about 76% w / w of the composition; and a humectant present in an amount of about 2% to about 6% w / w of the composition. In some embodiments, the solvent is a combination of water and ethanol. In some such embodiments, water is present in an amount of about 25% to about 30% w / w of the composition, and ethanol is present in an amount of about 45% to about 47% w / w of the composition. In some embodiments, the humectant is glycerol.

[0101] In some embodiments, the composition further comprises a thickening agent present in an amount of about 0.05% to about 0.20% w / w of the composition. In some embodiments, the thickening agent is a combination of hydroxyethyl cellulose and xanthan gum. In some such embodiments, the hydroxyethyl cellulose is present in an amount of about 0.04% to about 0.08% w / w of the composition, and the xanthan gum is present in an amount of about 0.04% to about 0.08% w / w of the composition.

[0102] In some embodiments, the composition further comprises a film-forming agent present in an amount of about 4% to about 6% w / w of the composition. In some embodiments, the film-forming agent is a combination of polymethylsilsesquioxane and an acrylate / C12-22 alkyl methacrylate copolymer. In some such embodiments, the polymethylsilsesquioxane is present in an amount of about 1% to about 5% w / w of the composition, and the acrylate / C12-22 alkyl methacrylate copolymer is present in an amount of about 1% to about 5% w / w of the composition.

[0103] In some embodiments, the composition further comprises a preservative present in an amount of 2% to about 4% w / w of the composition. In some embodiments, the preservative includes a combination of phenoxyethanol and ethylhexylglycerin. In some embodiments, the preservative includes a combination of phenoxyethanol, ethylhexylglycerin, and 1,2-hexanediol. In some such embodiments, the phenoxyethanol and ethylhexylglycerin are both present in the composition in an amount of about 0.1% to about 2% w / w of the composition. In some such embodiments, the phenoxyethanol and ethylhexylglycerin are present in the composition in a ratio of about 9:1 phenoxyethanol:ethylhexylglycerin. In some such embodiments, the 1,2-hexanediol is present in an amount of about 1% to about 3% w / w of the composition.

[0104] In some embodiments, the compositions provided herein comprise: genipin present in an amount of about 14% w / w of the composition; a solvent present in an amount of about 74% w / w of the composition; and a thickening agent present in an amount of about 0.12% w / w of the composition. In some embodiments, the solvent is a combination of water and ethanol. In some such embodiments, the water is present in an amount of about 28% w / w of the composition, and the ethanol is present in an amount of about 46% w / w of the composition. In some embodiments, the thickening agent is a combination of hydroxyethyl cellulose and xanthan gum. In some embodiments, the hydroxyethyl cellulose is present in an amount of about 0.06% w / w of the composition, and the xanthan gum is present in an amount of about 0.06% w / w of the composition.

[0105] In some embodiments, the composition further comprises a film-forming agent present in an amount of about 5% w / w of the composition. In some embodiments, the film-forming agent is a combination of polymethylsilsesquioxane and acrylates / C12-22 alkyl methacrylate copolymer. In some such embodiments, the polymethylsilsesquioxane is present in an amount of about 2% w / w of the composition, and the acrylates / C12-22 alkyl methacrylate copolymer is present in an amount of about 3% w / w of the composition. In some embodiments, the composition further comprises a humectant present in an amount of about 4% w / w of the composition. In some embodiments, the humectant is glycerol.

[0106] In some embodiments, the composition further comprises a preservative present in an amount of 3% w / w of the composition. In some embodiments, the preservative includes a combination of phenoxyethanol and ethylhexylglycerin. In some embodiments, the preservative includes a combination of phenoxyethanol, ethylhexylglycerin, and 1,2-hexanediol. In some such embodiments, phenoxyethanol and ethylhexylglycerin are both present in the composition in an amount of about 1% w / w of the composition. In some such embodiments, phenoxyethanol and ethylhexylglycerin are present in the composition in a ratio of about 9:1 phenoxyethanol:ethylhexylglycerin. In some such embodiments, 1,2-hexanediol is present in an amount of about 2% w / w of the composition.

[0107] In some embodiments, the compositions provided herein comprise: genipin present in an amount of about 14% w / w of the composition; a solvent present in an amount of about 74% w / w of the composition; and a humectant present in an amount of about 4% w / w of the composition. In some embodiments, the solvent is a combination of water and ethanol. In some such embodiments, the water is present in an amount of about 28% w / w of the composition, and the ethanol is present in an amount of about 46% w / w of the composition. In some embodiments, the humectant is glycerol.

[0108] In some embodiments, the composition further comprises a thickener present in an amount of about 0.12% w / w of the composition. In some embodiments, the thickener is a combination of hydroxyethyl cellulose and xanthan gum. In some such embodiments, the hydroxyethyl cellulose is present in an amount of about 0.06% w / w of the composition, and the xanthan gum is present in an amount of about 0.06% w / w of the composition.

[0109] In some embodiments, the composition further comprises a film-forming agent present in an amount of about 5% w / w of the composition. In some embodiments, the film-forming agent is a combination of polymethylsilsesquioxane and an acrylate / C12-22 alkyl methacrylate copolymer. In some such embodiments, the polymethylsilsesquioxane is present in an amount of about 2% w / w of the composition, and the acrylate / C12-22 alkyl methacrylate copolymer is present in an amount of about 3% w / w of the composition.

[0110] In some embodiments, the composition further comprises a preservative present in an amount of 3% w / w of the composition. In some embodiments, the preservative includes a combination of phenoxyethanol and ethylhexylglycerin. In some embodiments, the preservative includes a combination of phenoxyethanol, ethylhexylglycerin, and 1,2-hexanediol. In some such embodiments, phenoxyethanol and ethylhexylglycerin are both present in the composition in an amount of about 1% w / w of the composition. In some such embodiments, phenoxyethanol and ethylhexylglycerin are present in the composition in a ratio of about 9:1 phenoxyethanol:ethylhexylglycerin. In some such embodiments, 1,2-hexanediol is present in an amount of about 2% w / w of the composition.

[0111] In some embodiments, the compositions provided herein comprise: genipin present in an amount of about 5% to about 15% w / w of the composition; a solvent present in an amount of about 65% to about 85% w / w of the composition; and a film-forming agent present in an amount of about 5% to about 10% w / w of the composition.

[0112] In some embodiments, the compositions provided herein comprise: genipin present in an amount of about 9% to about 11% w / w of the composition; a solvent present in an amount of about 75% to about 80% w / w of the composition; and a film-forming agent present in an amount of about 6% to about 9% w / w of the composition.

[0113] In some embodiments, the solvent is a combination of water and ethanol. In some such embodiments, the water is present in an amount of about 25% to about 35% w / w of the composition, and the ethanol is present in an amount of about 45% to about 50% w / w of the composition. In some embodiments, the film-forming agent is a combination of an acrylate copolymer, polyvinylpyrrolidone, and a styrene / acrylate copolymer.

[0114] In some embodiments, the composition further comprises a humectant present in an amount of about 0.5% to about 1.5% w / w of the composition, hi some embodiments, the humectant is propanediol.

[0115] In some embodiments, the composition further comprises a preservative present in an amount of 0.5% to about 1.5% w / w of the composition. In some embodiments, the preservative includes a combination of phenoxyethanol and ethylhexylglycerin. In some embodiments, the preservative includes a combination of phenoxyethanol, ethylhexylglycerin, and EDTA. In some such embodiments, the phenoxyethanol and ethylhexylglycerin are both present in the composition in an amount of about 0.1% to about 2% w / w of the composition. In some such embodiments, the phenoxyethanol and ethylhexylglycerin are present in the composition in a ratio of about 9:1 phenoxyethanol:ethylhexylglycerin. In some such embodiments, EDTA is present in an amount of about 0.05% w / w of the composition.

[0116] In some embodiments, the compositions provided herein comprise: genipin present in an amount of about 10% w / w of the composition; a solvent present in an amount of about 77% w / w of the composition; and a film-forming agent present in an amount of about 7.5% w / w of the composition.

[0117] In some embodiments, the solvent is a combination of water and ethanol. In some such embodiments, the water is present in an amount of about 30% w / w of the composition and the ethanol is present in an amount of about 48% w / w of the composition. In some embodiments, the film-forming agent is a combination of an acrylate copolymer, polyvinylpyrrolidone, and a styrene / acrylate copolymer.

[0118] In some embodiments, the composition further comprises a humectant present in an amount of about 1% w / w of the composition, hi some embodiments, the humectant is propanediol.

[0119] In some embodiments, the composition further comprises a preservative present in an amount of about 1.05% w / w of the composition. In some embodiments, the preservative includes a combination of phenoxyethanol and ethylhexylglycerin. In some embodiments, the preservative includes a combination of phenoxyethanol, ethylhexylglycerin, and EDTA. In some such embodiments, the phenoxyethanol and ethylhexylglycerin are both present in the composition in an amount of about 1% w / w of the composition. In some such embodiments, the phenoxyethanol and ethylhexylglycerin are present in the composition in a ratio of about 9:1 phenoxyethanol:ethylhexylglycerin. In some such embodiments, the EDTA is present in an amount of about 0.05% w / w of the composition.

[0120] Also provided herein are methods of producing ink compositions, such as any of the ink compositions described herein. For example, such methods can include (i) combining a thickener with a first solvent to form a first solution, (ii) combining genipin with a second solvent to form a second solution, and (iii) combining the first and second solutions to form the ink composition. In some embodiments, a method of producing an ink composition as described herein includes (i) combining a thickener and a humectant with a first solvent to form a first solution, (ii) combining genipin and a film-forming agent (e.g., a first film-forming agent) with a second solvent to form a second solution, and (iii) combining the first and second solutions to form the ink composition. In some embodiments, the methods described herein further include iv) adding a film-forming agent (e.g., a first or second film-forming agent) and / or a preservative to the ink composition.

[0121] In some embodiments, the first solvent is any of the solvents described herein. In some embodiments, the second solvent is any of the solvents described herein. In some embodiments, the first solvent and the second solvent are different.

[0122] In some embodiments, the first solvent is water. In some embodiments, the second solvent is ethanol.

[0123] In some embodiments, the thickening agent (e.g., any of the thickening agents described herein) and the first solvent are present in the first solution in a ratio of thickening agent:first solvent of about 1:500 to about 4:500, hi some embodiments, the thickening agent and the first solvent are present in the first solution in a ratio of thickening agent:first solvent of about 2:500.

[0124] In some embodiments, the thickening agent is a combination of hydroxyethyl cellulose and xanthan gum. In some embodiments, the combination of hydroxyethyl cellulose and xanthan gum is present in a ratio of hydroxyethyl cellulose:xanthan gum of about 2:1 to about 1:2. In some embodiments, the combination of hydroxyethyl cellulose and xanthan gum is present in a ratio of hydroxyethyl cellulose:xanthan gum of about 1:1.

[0125] In some embodiments, the thickening agent, humectant (e.g., any of the humectants described herein), and first solvent are present in the first solution in a ratio of thickening agent:humectant:first solvent of about 1:15:234 to about 1:62:187. In some embodiments, the thickening agent and first solvent are present in the first solution in a ratio of thickening agent:humectant:first solvent of about 1:31:218.

[0126] In some embodiments, the humectant is glycerin.

[0127] In some embodiments, the first solution is incubated at a temperature of about 70°C to about 120°C, such as about 70°C to about 75°C, about 70°C to about 80°C, about 70°C to about 85°C, about 70°C to about 90°C, about 70°C to about 95°C, about 70°C to about 100°C, about 70°C to about 105°C, about 70°C to about 110°C, about 70°C to about 115°C, about 115°C to about 120°C, about 110°C to about 120°C, about 105°C to about 120°C, about 100°C to about 120°C, about 95°C to about 120°C, about 90°C to about 120°C, about 85°C to about 120°C, about 80°C to about 120°C, or about 75°C to about 120°C. In some embodiments, the first solution is incubated at a temperature of about 80°C to about 105°C, about 85°C to about 100°C, or about 90°C to about 95°C.

[0128] In some embodiments, the first solution is stirred.

[0129] In some embodiments, the first solution is incubated and / or stirred until the thickening agent dissolves.

[0130] In some embodiments, the genipin and second solvent are present in the second solution in a ratio of genipin:second solvent of about 4:25 to about 3:5. In some embodiments, the genipin and second solvent are present in the second solution in a ratio of genipin:second solvent of about 3:10.

[0131] In some embodiments, the genipin, first film-forming agent (e.g., any of the film-forming agents described herein), and second solvent are present in the second solution in a ratio of about 57:16:177 to about 57:4:189 genipin:film-forming agent:second solvent. In some embodiments, the genipin, first film-forming agent, and second solvent are present in the second solution in a ratio of about 57:8:185 genipin:film-forming agent:second solvent. In some embodiments, the first film-forming agent is polymethylsilsesquioxane.

[0132] In some embodiments, the second solution is incubated at a temperature of about 30°C to about 60°C, for example, about 30°C to about 35°C, about 30°C to about 40°C, about 30°C to about 45°C, about 30°C to about 50°C, about 30°C to about 55°C, about 55°C to about 60°C, about 50°C to about 60°C, about 45°C to about 60°C, about 40°C to about 60°C, or about 35°C to about 60°C. In some embodiments, the second solution is incubated at a temperature of about 35°C to about 55°C, about 35°C to about 45°C, about 40°C to about 50°C, or about 45°C to about 55°C.

[0133] In some embodiments, the second solution is stirred.

[0134] In some embodiments, the second solution is incubated and / or stirred until the genipin dissolves.

[0135] In some embodiments, the temperature of the first solution is cooled. In some embodiments, the temperature of the first solution is cooled to about 20°C to about 50°C. For example, about 20°C to about 25°C, about 20°C to about 30°C, about 20°C to about 35°C, about 20°C to about 40°C, about 20°C to about 45°C, about 45°C to about 50°C, about 40°C to about 50°C, about 35°C to about 50°C, about 30°C to about 50°C, or about 25°C to about 50°C. In some embodiments, the temperature of the first solution is cooled to about 35°C to about 45°C. For example, about 35°C, about 36°C, about 37°C, about 38°C, about 39°C, about 40°C, about 41°C, about 42°C, about 43°C, about 44°C, or about 45°C.

[0136] In some embodiments, the temperature of the second solution is cooled. In some embodiments, the temperature of the second solution is cooled to about 20°C to about 50°C. For example, about 20°C to about 25°C, about 20°C to about 30°C, about 20°C to about 35°C, about 20°C to about 40°C, about 20°C to about 45°C, about 45°C to about 50°C, about 40°C to about 50°C, about 35°C to about 50°C, about 30°C to about 50°C, or about 25°C to about 50°C. In some embodiments, the temperature of the second solution is cooled to about 35°C to about 45°C. For example, about 35°C, about 36°C, about 37°C, about 38°C, about 39°C, about 40°C, about 41°C, about 42°C, about 43°C, about 44°C, or about 45°C.

[0137] In some embodiments, the first solution and the second solution are present in the ink composition in a ratio of first solution:second solution of about 1:4 to about 1:1. In some embodiments, the first solution and the second solution are present in the ink composition in a ratio of first solution:second solution of about 1:2.

[0138] In some embodiments, combining the first and second solutions to form the ink composition comprises stirring, hi some embodiments, the ink composition is stirred until the ink composition is clear and free of any visible suspended particles.

[0139] In some embodiments, the ink composition is cooled to about room temperature. In some embodiments, the ink composition is cooled to about 20°C to about 30°C. In some embodiments, the ink composition is cooled to about 25°C.

[0140] In some embodiments, the ink composition is cooled before adding a film-forming agent (e.g., the first or second film-forming agent) and / or a preservative to the ink composition. In some embodiments, adding a film-forming agent (e.g., the first or second film-forming agent) and / or a preservative to the ink composition further comprises agitating the ink composition.

[0141] In some embodiments, the film-forming agent (e.g., any of the film-forming agents described herein) is present in an amount of about 1% to about 10% w / w of the ink composition. In some embodiments, the film-forming agent is present in an amount of about 2% to about 6% w / w of the ink composition. In some embodiments, the film-forming agent is selected from the group consisting of polymethylsilsesquioxane, acrylate / C12-22 alkyl methacrylate copolymer, and combinations thereof.

[0142] In some embodiments, the second film-forming agent (e.g., any of the film-forming agents described herein) is present in an amount of about 1% to about 5% w / w of the ink composition. In some embodiments, the second film-forming agent is present in an amount of about 3% w / w of the ink composition. In some embodiments, the first film-forming agent and the second film-forming agent are different.

[0143] In some embodiments, the second film-forming agent is an acrylate / C12-22 alkyl methacrylate copolymer.

[0144] In some embodiments, the preservative (e.g., any of the preservatives described herein) is present in an amount of about 0.1% to about 5% w / w of the ink composition. In some embodiments, the preservative is present in an amount of about 2% to about 4% w / w of the ink composition. In some embodiments, the preservative is present in an amount of about 3% w / w of the ink composition.

[0145] In some embodiments, the preservative comprises a combination of phenoxyethanol and ethylhexylglycerin. In some embodiments, the phenoxyethanol and ethylhexylglycerin are present in the composition in a ratio of about 9:1 phenoxyethanol:ethylhexylglycerin. In some embodiments, the combination of phenoxyethanol and ethylhexylglycerin is present in an amount of about 0.1% to about 2% w / w of the ink composition. In some embodiments, the combination of phenoxyethanol and ethylhexylglycerin is present in an amount of about 1% w / w of the ink composition.

[0146] In some embodiments, the preservative comprises 1,2-hexanediol. In some embodiments, the 1,2-hexanediol is present in an amount of about 1% to about 3% w / w of the ink composition. In some embodiments, the 1,2-hexanediol is present in an amount of about 2% w / w of the ink composition.

[0147] In some embodiments, a method of making an ink composition as described herein includes: i) combining genipin with a first solvent to form a genipin solution; ii) combining a film-forming agent (e.g., a first film-forming agent) with a second solvent to form a solution (e.g., a first solution or a subsequent solution); and iii) combining the genipin solution with a solution (e.g., the first solution or a subsequent solution) to form the ink composition. In some embodiments, the methods described herein can further include adding one or more of a film-forming agent (e.g., a second or third film-forming agent), a humectant (e.g., a first humectant), a preservative (e.g., a first preservative), and a temporary colorant (e.g., a first temporary colorant) to the genipin solution, the solution (e.g., the first solution or a subsequent solution), or the ink composition. In some embodiments, the methods described herein include adding one or more of a film-forming agent (e.g., a second or third film-forming agent), a humectant (e.g., a first humectant), and a preservative (e.g., a first humectant) to a solution (e.g., a first solution) to form a second solution (or a third solution, a fourth solution, etc., or a subsequent solution).

[0148] In some embodiments, the first solvent is any of the solvents described herein. In some embodiments, the second solvent is any of the solvents described herein. In some embodiments, the first solvent and the second solvent are different.

[0149] In some embodiments, the first solvent comprises ethanol. In some embodiments, the first solvent comprises ethanol and water. In some embodiments, the second solvent comprises water.

[0150] In some embodiments, the genipin and first solvent are present in the genipin solution in a ratio of about 4:25 to about 3:5 genipin:first solvent. In some embodiments, the genipin and first solvent are present in the genipin solution in a ratio of about 1:5 genipin:first solvent.

[0151] In some embodiments, the genipin solution is stirred. In some embodiments, the genipin solution is stirred until the genipin is dissolved.

[0152] In some embodiments, the film-forming agent (e.g., a first film-forming agent) and the second solvent are present in solution at a ratio of film-forming agent:second solvent of about 1:40 to about 1:120. In some embodiments, the film-forming agent and the second solvent are present in solution at a ratio of film-forming agent:second solvent of about 1:80.

[0153] In some embodiments, the film-forming agent (e.g., the first film-forming agent) is any of the film-forming agents described herein. In some embodiments, the film-forming agent comprises an acrylate copolymer.

[0154] In some embodiments, the solution (e.g., the first solution) is stirred. In some embodiments, the solution (e.g., the first solution) is stirred until the film-forming agent (e.g., the first film-forming agent) is dispersed.

[0155] In some embodiments, a second film-forming agent is combined with the first solution to form a second solution. In some embodiments, the second film-forming agent and the first solution are present in the second solution in a ratio of second film-forming agent:first solution of about 1:10 to about 1:40. In some embodiments, the second film-forming agent and the first solution are present in the second solution in a ratio of second film-forming agent:first solution of about 1:21.

[0156] In some embodiments, the second film-forming agent is any of the film-forming agents described herein, hi some embodiments, the second film-forming agent comprises polyvinylpyrrolidone.

[0157] In some embodiments, the second solution is stirred.

[0158] In some embodiments, a third film-forming agent is combined with the second solution to form a third solution. In some embodiments, the third film-forming agent and the second solution are present in the third solution in a ratio of about 1:2 to about 1:10 third film-forming agent:second solution. In some embodiments, the third film-forming agent and the second solution are present in the third solution in a ratio of about 3:11 third film-forming agent:second solution.

[0159] In some embodiments, the third film-forming agent is any of the film-forming agents described herein, hi some embodiments, the third film-forming agent comprises a styrene / acrylate copolymer.

[0160] In some embodiments, the third solution is stirred.

[0161] In some embodiments, the humectant is combined with a solution (e.g., the first solution, the second solution, or the third solution) to form a fourth solution. In some embodiments, the humectant is combined with the third solution to form the fourth solution. In some embodiments, the humectant and the solution (e.g., the third solution) are present in the fourth solution at a humectant:solution ratio of about 1:10 to about 1:40. In some embodiments, the humectant and the solution (e.g., the third solution) are present in the fourth solution at a humectant:solution ratio of about 1:28.

[0162] In some embodiments, the humectant is any of the humectants described herein, hi some embodiments, the humectant comprises propanediol.

[0163] In some embodiments, the fourth solution is stirred.

[0164] In some embodiments, the preservative is combined with a solution (e.g., the first solution, the second solution, the third solution, or the fourth solution) to form a fifth solution. In some embodiments, the preservative is combined with the fourth solution to form the fifth solution. In some embodiments, the preservative and the solution (e.g., the fourth solution) are present in the fifth solution at a preservative:solution ratio of about 1:10 to about 1:40. In some embodiments, the preservative and the solution (e.g., the fourth solution) are present in the fifth solution at a preservative:solution ratio of about 1:28.

[0165] In some embodiments, the preservative is any of the preservatives described herein. In some embodiments, the preservative comprises a combination of phenoxyethanol and ethylhexylglycerin. In some embodiments, the preservative comprises a combination of phenoxyethanol, ethylhexylglycerin, and EDTA. In some embodiments, the phenoxyethanol and ethylhexylglycerin are combined with the solution (e.g., the fourth solution) before the EDTA is combined with the solution. In some embodiments, the solution (e.g., the fourth solution) is stirred between combining the phenoxyethanol and ethylhexylglycerin with the solution (e.g., the fourth solution) and combining the EDTA with the solution (e.g., the fourth solution).

[0166] In some embodiments, the phenoxyethanol and ethylhexylglycerin are present in the composition in a ratio of about 9:1 phenoxyethanol:ethylhexylglycerin.

[0167] In some embodiments, the fifth solution is stirred.

[0168] In some embodiments, the genipin solution and the solution (e.g., the first solution, the second solution, the third solution, the fourth solution, or the fifth solution) are present in the ink composition at a genipin solution:solution ratio of about 1:6 to about 1:1. In some embodiments, the genipin solution and the solution (e.g., the first solution, the second solution, the third solution, the fourth solution, or the fifth solution) are present in the ink composition at a genipin solution:solution ratio of about 1:2.

[0169] In some embodiments, combining the genipin solution and the second solution to form the ink composition includes stirring, hi some embodiments, the ink composition is stirred until the ink composition is clear and free of any visible suspended particles.

[0170] In some embodiments, a temporary colorant (e.g., any of the temporary colorants described herein) is combined with the ink composition. In some embodiments, the temporary colorant is present in an amount of about 0.1% to about 10% w / w of the ink composition. In some embodiments, the temporary colorant is present in an amount of about 2.5% w / w of the ink composition. In some embodiments, the temporary colorant comprises D&C Black No. 2.

[0171] Also provided herein are compositions prepared by any of the methods described above. [Example]

[0172] The present invention will be further described in detail by specific examples.The following examples are provided for illustrative purposes, and are intended to illustrate the topical compositions and methods described herein, and are not intended to limit the present invention in any way.Many variations suggest themselves and are completely within the intended scope.Those skilled in the art will easily recognize various non-critical parameters that can be changed or modified to produce essentially the same results.

[0173] Example 1. Ink composition 0.03 g of hydroethylcellulose (e.g., NATROSOL® 250HHR CS), 0.03 g of xanthan gum (e.g., KELTROL® CG), and 2 g of glycerol were added to 14.2 g of water (Phase A) and mixed at a temperature of approximately 90°C to 95°C until the hydroethylcellulose and xanthan gum were completely dissolved. The temperature was then reduced to 40°C.

[0174] 7 g of genipin (e.g., genipa plant extract) and 1 g of polymethylsilsesquioxane (e.g., GRANSIL™ PSQ) were added to 22.8 g of ethanol (Phase B) and mixed at a temperature of approximately 40°C to 50°C. Decomposition of genipin should be avoided. After the genipin was completely suspended in the solution, the temperature was reduced to 40°C.

[0175] Phase A and Phase B were mixed until the solution was clear and free of any visible suspended particles. The ink mixture was then allowed to come to room temperature.

[0176] 1.5 g of acrylates / C12-22 alkyl methacrylate copolymer (e.g., ALLIANZ™ OPT polymer), 0.5 g of a combination of phenoxyethanol and ethylhexylglycerin (e.g., EUXYL® PE9010), and 1 g of 1,2-hexanediol (e.g., OPTIPHEN® HD) were added to the ink mixture and mixed until a homogeneous solution was obtained. The final amounts are shown in Table 1. [Table 1]

[0177] Example 2. Ink composition Genipin and ethanol were mixed together until the genipin dissolved and a clear amber solution was obtained (Phase A). The solution was stirred at 500 rpm on an IKA mixer for 15 minutes.

[0178] An acrylate copolymer (e.g., CARBOPOL® Aqua SF1) was added to the water (Phase B). The mixture was mixed at 500 rpm for 5-7 minutes.

[0179] Phase C was added to Phase B with continuous mixing until the powder was dispersed. The mixture was stirred at 500 rpm for 5-7 minutes.

[0180] Phase D was added to Phase B+C with continuous mixing until the mixture was homogenous. The mixture of Phases B+C+D was stirred at 500 rpm for 5-7 minutes.

[0181] Phase E was added to Phases B+C+D with continuous mixing until the mixture was homogenous. The mixture of Phases B+C+D+E was stirred at 500 rpm for 5-7 minutes.

[0182] Phase F was added to Phases B+C+D+E with continuous mixing until the mixture was homogenous. The mixture of Phases B+C+D+E+F was stirred at 500 rpm for 5-7 minutes.

[0183] Phase G was added to Phases B+C+D+E+F with continuous mixing until the mixture was homogenous. The Phase B+C+D+E+F+G mixture was stirred at 500 rpm for 5-7 minutes.

[0184] Phase B+C+D+E+F+G was added to Phase A with continuous mixing until the mixture was homogenous. The Phase B+C+D+E+F+G+A mixture was stirred at 500 rpm for 10-15 minutes.

[0185] Phase H was added to Phases B+C+D+E+F+G+A. The mixture of Phases B+C+D+E+F+G+A+H was stirred at 800-1000 rpm for 10 minutes until the mixture was homogenous. [Table 2]

[0186] Other embodiments Embodiment 1 is a composition comprising a semi-permanent colorant, a solvent, and a thickener.

[0187] Embodiment 2 is the composition of embodiment 1, wherein the semi-permanent colorant is present in an amount of about 10% to about 20% w / w of the composition.

[0188] Embodiment 3 is the composition of embodiment 1 or 2, wherein the semi-permanent colorant is present in an amount from about 12% to about 16% w / w of the composition.

[0189] Embodiment 4 is the composition of any one of embodiments 1-3, wherein the semi-permanent colorant is present in an amount of about 14% w / w of the composition.

[0190] Embodiment 5 is the composition of any one of embodiments 1-4, wherein the semi-permanent colorant is genipin.

[0191] Embodiment 6 is the composition of any one of embodiments 1-5, wherein the solvent is present in an amount of about 65% to about 80% w / w of the composition.

[0192] Embodiment 7 is the composition of any one of embodiments 1-6, wherein the solvent is present in an amount of about 72% to about 76% w / w of the composition.

[0193] Embodiment 8 is the composition of any one of embodiments 1-7, wherein the solvent is present in an amount of about 74% w / w of the composition.

[0194] Embodiment 9 is the composition of any one of embodiments 1-8, wherein the solvent comprises water, methanol, ethanol, isopropanol, diethylene glycol monoethyl ether, or a combination thereof.

[0195] Embodiment 10 is the composition of any one of embodiments 1-9, wherein the solvent is a combination of water and ethanol.

[0196] Embodiment 11 is the composition of any one of embodiments 1-10, wherein the water is present in an amount of about 25% to about 30% w / w of the composition.

[0197] Embodiment 12 is the composition of any one of embodiments 1-11, wherein the water is present in an amount of about 28% w / w of the composition.

[0198] Embodiment 13 is the composition of any one of embodiments 1-12, wherein the ethanol is present in an amount of about 40% to about 50% w / w of the composition.

[0199] Embodiment 14 is the composition of any one of embodiments 1-13, wherein the ethanol is present in an amount of about 45% to about 47% w / w of the composition.

[0200] Embodiment 15 is the composition of any one of embodiments 1-14, wherein the ethanol is present in an amount of about 46% w / w of the composition.

[0201] Embodiment 16 is the composition of any one of embodiments 1-15, wherein the thickening agent is present in an amount from about 0.01% to about 0.3% w / w of the composition.

[0202] Embodiment 17 is the composition of any one of embodiments 1-16, wherein the thickening agent is present in an amount from about 0.05% to about 0.2% w / w of the composition.

[0203] Embodiment 18 is the composition of any one of embodiments 1-17, wherein the thickening agent is present in an amount of about 0.12% w / w of the composition.

[0204] Embodiment 19 is the composition of any one of embodiments 1-18, wherein the thickening agent comprises hydroxyethylcellulose, xanthan gum, arabinogalactan, aluminum starch octenylsuccinate, xanthan gum, sclerotium gum, tragacanth gum, pectin, karaya gum, gum arabic, agar, guar gum, carrageenan, locust bean gum, alginate, arginine, gelatin, tara gum, ghatti gum, gellan gum, konjac gum, cassia gum, spruce gum, chicle gum, dammar, curdlan gum, pullulan, hydroxypropyl cellulose, hydroxypropyl methylcellulose, ethyl cellulose, soybean hemicellulose, sodium carboxymethylcellulose, or combinations thereof.

[0205] Embodiment 20 is the composition of any one of embodiments 1-19, wherein the thickening agent is a combination of hydroxyethyl cellulose and xanthan gum.

[0206] Embodiment 21 is the composition of embodiment 19 or 20, wherein the hydroxyethyl cellulose is present in an amount from about 0.01% to about 0.1% w / w of the composition.

[0207] Embodiment 22 is the composition of any one of embodiments 19-21, wherein the hydroxyethyl cellulose is present in an amount from about 0.04% to about 0.08% w / w of the composition.

[0208] Embodiment 23 is the composition of any one of embodiments 19-22, wherein the hydroxyethyl cellulose is present in an amount of about 0.06% w / w of the composition.

[0209] Embodiment 24 is the composition of any one of embodiments 19-23, wherein the xanthan gum is present in an amount from about 0.01% to about 0.1% w / w of the composition.

[0210] Embodiment 25 is the composition of any one of embodiments 19-24, wherein the xanthan gum is present in an amount from about 0.04% to about 0.08% w / w of the composition.

[0211] Embodiment 26 is the composition of any one of embodiments 19-25, wherein the xanthan gum is present in an amount of about 0.06% w / w of the composition.

[0212] Embodiment 27 is the composition of any one of embodiments 1-26, wherein the composition further comprises a film-forming agent.

[0213] Embodiment 28 is the composition of any one of embodiments 1-27, wherein the film forming agent is present in an amount from about 0.1% to about 10% w / w of the composition.

[0214] Embodiment 29 is the composition of any one of embodiments 1-28, wherein the film forming agent is present in an amount of about 4% to about 6% w / w of the composition.

[0215] Embodiment 30 is the composition of any one of embodiments 1-29, wherein the film forming agent is present in an amount of about 5% w / w of the composition.

[0216] Embodiment 31 is the composition of any one of embodiments 1-30, wherein the film-forming agent comprises a volatile silicone resin, polyvinylpyrrolidone, acrylate, acrylamide, copolymer, isododecane resin, or a combination thereof.

[0217] Embodiment 32 is the composition of any one of embodiments 1-31, wherein the film former is selected from the group consisting of polymethylsilsesquioxane, trimethylsiloxysilicate, polypropylsilsesquioxane, dimethicone, cyclopentasiloxane, dimethiconol crosspolymer, polysilicone-6, polysilicone-8, polysilicone-11, polysilicone-14, acrylates / C12-22 alkyl methacrylate copolymer, acrylates / polytrimethylsiloxymethacrylate copolymer, polyvinylpyrrolidone / vinyl acetate (VP / VA) copolymer, and VP / dimethiconyl acrylate. and / or VP / polycarbamyl / polyglycol ester, VP / dimethylaminoethyl methacrylate copolymer, VP / dimethylaminoethyl methacrylate / polycarbamyl polyglycol ester, VP / eicosene copolymer, VP / hexadecene copolymer, VP / methacrylamide / vinylimidazole copolymer, VP / polycarbamyl polyglycol ester, VP / VA copolymer, polyester-1, polyester-2, polyester-3, polyester-4, polyester-5, polyester-7, polyester-8, polyester-10, or combinations thereof.

[0218] Embodiment 33 is the composition of any one of embodiments 1-32, wherein the film former is a combination of polymethylsilsesquioxane and an acrylate / C12-22 alkyl methacrylate copolymer.

[0219] Embodiment 34 is the composition of embodiment 32 or 33, wherein the polymethylsilsesquioxane is present in an amount from about 1% to about 5% w / w of the composition.

[0220] Embodiment 35 is the composition of any one of embodiments 32-34, wherein the polymethylsilsesquioxane is present in an amount of about 2% w / w of the composition.

[0221] Embodiment 36 is the composition of any one of embodiments 32-35, wherein the acrylates / C12-22 alkyl methacrylate copolymer is present in an amount from about 1% to about 5% w / w of the composition.

[0222] Embodiment 37 is the composition of any one of embodiments 32-36, wherein the acrylates / C12-22 alkyl methacrylate copolymer is present in an amount of about 3% w / w of the composition.

[0223] Embodiment 38 is the composition of any one of embodiments 1-37, wherein the composition further comprises a moisturizer.

[0224] Embodiment 39 is the composition of any one of embodiments 1-38, wherein the humectant is present in an amount from about 1% to about 10% w / w of the composition.

[0225] Embodiment 40 is the composition of any one of embodiments 1-39, wherein the humectant is present in an amount from about 2% to about 6% w / w of the composition.

[0226] Embodiment 41 is the composition of any one of embodiments 1-40, wherein the humectant is present in an amount of about 4% w / w of the composition.

[0227] Embodiment 42 is the composition of any one of embodiments 1-41, wherein the moisturizer comprises aloe vera gel, lithium chloride, allantoin, urea, dicyanamidoglycerol, lactic acid, propylene glycol, polyethylene glycol, dipropylene glycol, polypropylene glycol, polyethylene glycol and its derivatives, hexylene glycol, 1,3-butylene glycol, 1,2,6-hexanetriol, glycerol ethoxylate, glycerol propoxylate, glyceryl triacetate, sorbitol, hydroxypropyl sorbitol, xylitol, maltitol, hyaluronic acid, Tremella extract, sodium lactate, sodium urea L-pyroglutamate, and pyrrolidone carboxylic acid, or a combination thereof.

[0228] Embodiment 43 is the composition of any one of embodiments 1-42, wherein the humectant is glycerin.

[0229] Embodiment 44 is the composition of any one of embodiments 1 to 43, wherein the composition further comprises a preservative.

[0230] Embodiment 45 is the composition of embodiment 44, wherein the preservative is present in an amount from about 0.1% to about 5% w / w of the composition.

[0231] Embodiment 46 is the composition of embodiment 44 or 45, wherein the preservative is present in an amount of about 2% to about 4% w / w of the composition.

[0232] Embodiment 47 is the composition of any one of embodiments 44-46, wherein the humectant is present in an amount of about 3% w / w of the composition.

[0233] Embodiment 48 is the composition of any one of embodiments 44 to 47, wherein the preservative is selected from the group consisting of ascorbic acid, ascorbate, palmitate, citric acid, benzoate, benzoic acid, propionate, propionic acid, sorbate, sorbic acid, salicylic acid, salicylate, hexa-2,4-dienoic acid, hexa-2,4-dienoate, formaldehyde, formaldehyde-releasing agents, formic acid and its salts, 3-acetyl-6-methylpyran-2,4-(3H)-dione and its salts, 3,3'-dibromo-4,4'-hexamethylenedioxydibenzamidine and its salts, thiomersal, phenylmercury salts, undec-10-enoic acid and its salts, 1,3-bis(2 -ethylhexyl)hexahydro-5-methyl-5-pyrimidine, 5-bromo-5-nitro-1,3-dioxane, bronopol, 2,4-dichlorobenzyl alcohol, 1-(4-chlorophenyl)-3-(3,4-dichlorophenyl)urea, chlorocresol, chloroxylenol, 5-chloro-2-(2,4-dichlorophenoxy)phenol, N,N"-methylenebis[N'-[3-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]urea], polyaminopropyl biguanide, methenamine, quaternium-15, climbazole, DMDM ​​hydantoin, benzyl alcohol, 1-hydroxy-4-methyl-6-(2,4,4-Trimethylpentyl)-2-pyridone, piroctone olamine, bromochlorophene, o-cymen-5-ol, chlorophene, chloroacetamine, methylchloroisothiazolinone, methylisothiazolinone, phenoxyisopropanol, chlorhexidine, chlorhexidine diacetate, chlorhexidine digluconate, chlorhexidine dihydrochloride, dimethyloxazolidine, behentrimonium chloride, cetrimonium bromide, cetrimonium chloride, laurtrimonium bromide, laurtrimonium chloride, steartrimonium bromide, steartrimonium chloride, diazolidinyl urea, hexamidine, hexamidine diisethionate, hexamidine paraben, glutaral, 7-ethylbicyclooxazolidine, chlorphenesin, sodium hydroxymethylglycine, silver chloride, salt Benzethonium chloride, benzalkonium chloride, benzalkonium bromide, benzalkonium saccharinate, benzyl hemiformal, iodopropynyl butylcarbamate, biphenyl-2-ol and its salts, zinc pyrithione, erythorbate, nitrous acid, ethylenediaminetetraacetic acid (EDTA), butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), caprylic acid, dilauryl thiodipropionate, erythorbic acid, guaiac butter, methylparaben, sulfite, bisulfite, metabisulfite, propylparaben, stannous chloride, sulfur dioxide, thiodipropionic acid, isothiazolinone, parabens, phenoxyethanol, ethylhexylglycerin, glycol, tocopherol, 1,2-hexanediol, or combinations thereof.

[0234] Embodiment 49 is the composition of any one of embodiments 44-48, wherein the preservative is a combination of phenoxyethanol and ethylhexylglycerin.

[0235] Embodiment 50 is the composition of embodiment 49, wherein the phenoxyethanol and ethylhexylglycerin are present in the composition in a ratio of about 9:1 phenoxyethanol:ethylhexylglycerin.

[0236] Embodiment 51 is the composition of embodiment 49 or 50, wherein the combination of phenoxyethanol and ethylhexylglycerin is present in an amount from about 0.1% to about 2% w / w of the composition.

[0237] Embodiment 52 is the composition of any one of embodiments 49-51, wherein the combination of phenoxyethanol and ethylhexylglycerin is present in an amount of about 1% w / w of the composition.

[0238] Embodiment 53 is the composition of any one of embodiments 49-52, wherein the preservative comprises 1,2 hexanediol.

[0239] Embodiment 54 is the composition of any one of embodiments 49-53, wherein the 1,2 hexanediol is present in an amount from about 1% to about 3% w / w of the composition.

[0240] Embodiment 55 is the composition of any one of embodiments 49-54, wherein the 1,2 hexanediol is present in an amount of about 2% w / w of the composition.

[0241] Embodiment 56 is a method of making an ink composition, the method including: i. combining a thickener with a first solvent to form a first solution; ii. combining genipin with a second solvent to form a second solution; and iii. combining the first solution and the second solution to form the ink composition.

[0242] Embodiment 57 is the method of embodiment 56, further comprising adding a film-forming agent, a preservative, or a combination thereof to the ink composition.

[0243] Embodiment 58 is a method of making an ink composition, the method including: i. combining a thickener and a humectant with a first solvent to form a first solution; ii. combining genipin and a first film-forming agent with a second solvent to form a second solution; and iii. combining the first solution and the second solution to form the ink composition.

[0244] Embodiment 59 is the method of embodiment 58, further comprising adding a second film-forming agent, a preservative, or a combination thereof to the ink composition.

[0245] Embodiment 60 is the method of any one of embodiments 56 to 59, wherein the first solution is incubated at a temperature of about 70°C to about 120°C.

[0246] Embodiment 61 is the method of any one of embodiments 56 to 59, wherein the first solution is incubated at a temperature of about 90°C to about 95°C.

[0247] Embodiment 62 is the method of any one of embodiments 56 to 61, wherein the first solution is stirred.

[0248] Embodiment 63 is the method of any one of embodiments 56-62, wherein the thickening agent is dissolved in the first solution before combining the first and second solutions.

[0249] Embodiment 64 is the method of any one of embodiments 56 to 63, wherein the second solution is incubated at a temperature of about 30°C to about 60°C.

[0250] Embodiment 65 is the method of any one of embodiments 56 to 64, wherein the second solution is incubated at a temperature of about 40°C to about 50°C.

[0251] Embodiment 66 is the method of any one of embodiments 56 to 65, wherein the second solution is stirred.

[0252] Embodiment 67 is the method of any one of embodiments 60-66, wherein the first solution is cooled to a temperature of about 20°C to about 50°C.

[0253] Embodiment 68 is the method of any one of embodiments 60-67, wherein the first solution is cooled to a temperature of about 40°C.

[0254] Embodiment 69 is the method of any one of embodiments 65-68, wherein the second solution is cooled to a temperature of about 20°C to about 50°C.

[0255] Embodiment 70 is the method of any one of embodiments 65-69, wherein the first solution is cooled to a temperature of about 40°C.

[0256] Embodiment 71 is the method of any one of embodiments 5670, wherein the ink composition is agitated.

[0257] Embodiment 72 is the method of any one of embodiments 65 to 68, wherein the ink composition is cooled to a temperature of about 20°C to about 30°C.

[0258] Embodiment 73 is the method of any one of embodiments 65 to 69, wherein the ink composition is cooled to a temperature of about 25°C.

[0259] Embodiment 74 is the method of embodiment 72 or 73, wherein the ink composition is cooled before adding the film-forming agent, the preservative, or a combination thereof to the ink composition.

[0260] Embodiment 75 is the method of any one of embodiments 55 to 74, wherein the thickener and first solvent are present in the first solution in a ratio of thickener:first solvent of about 1:500 to about 4:500.

[0261] Embodiment 76 is the method of any one of embodiments 56 to 75, wherein the thickener and first solvent are present in the first solution in a ratio of thickener:first solvent of about 2:500.

[0262] Embodiment 77 is the method of any one of embodiments 56 to 75, wherein the first solvent comprises water, methanol, ethanol, isopropanol, diethylene glycol monoethyl ether, or a combination thereof.

[0263] Embodiment 78 is the method of any one of embodiments 56 to 75, wherein the first solvent comprises water.

[0264] Embodiment 79 is the method of any one of embodiments 56 to 78, wherein the thickening agent comprises hydroxyethylcellulose, xanthan gum, arabinogalactan, aluminum starch octenylsuccinate, xanthan gum, sclerotium gum, tragacanth gum, pectin, karaya gum, gum arabic, agar, guar gum, carrageenan, locust bean gum, alginate, arginine, gelatin, tara gum, ghatti gum, gellan gum, konjac gum, cassia gum, spruce gum, chicle gum, dammar, curdlan gum, pullulan, hydroxypropyl cellulose, hydroxypropyl methylcellulose, ethylcellulose, soybean hemicellulose, sodium carboxymethylcellulose, or combinations thereof.

[0265] Embodiment 80 is the method of any one of embodiments 56-79, wherein the thickening agent is a combination of hydroxyethyl cellulose and xanthan gum.

[0266] Embodiment 81 is the method of embodiment 80, wherein the combination of hydroxyethyl cellulose and xanthan gum is present in a ratio of 1:1 hydroxyethyl cellulose:xanthan gum.

[0267] Embodiment 82 is the method of any one of embodiments 58-81, wherein the thickening agent, humectant, and first solvent are present in the first solution in a ratio of thickening agent:humectant:first solvent of about 1:15:234 to about 1:62:187.

[0268] Embodiment 83 is the method of any one of embodiments 58 to 82, wherein the thickener and first solvent are present in the first solution in a ratio of thickener:humectant:first solvent of about 1:31:218.

[0269] Embodiment 84 is the method of any one of embodiments 58 to 83, wherein the moisturizer comprises aloe vera gel, lithium chloride, allantoin, urea, dicyanamidoglycerol, lactic acid, propylene glycol, polyethylene glycol, dipropylene glycol, polypropylene glycol, polyethylene glycol and its derivatives, hexylene glycol, 1,3-butylene glycol, 1,2,6-hexanetriol, ethoxylated glycerol, propoxylated glycerol, glyceryl triacetate, sorbitol, hydroxypropyl sorbitol, xylitol, maltitol, hyaluronic acid, Tremella extract, sodium lactate, sodium urea-L-pyroglutamate, and pyrrolidone carboxylic acid, or a combination thereof.

[0270] Embodiment 85 is the method of any one of embodiments 58-84, wherein the humectant is glycerin.

[0271] Embodiment 86 is the method of any one of embodiments 56-85, wherein the genipin and second solvent are present in the second solution in a ratio of genipin:second solvent of about 4:25 to about 3:5.

[0272] Embodiment 87 is the method of any one of embodiments 56-86, wherein the genipin and second solvent are present in the second solution in a ratio of about 3:10 genipin:second solvent.

[0273] Embodiment 88 is the method of any one of embodiments 56-87, wherein the second solvent comprises water, methanol, ethanol, isopropanol, diethylene glycol monoethyl ether, or a combination thereof.

[0274] Embodiment 89 is the method of any one of embodiments 56 to 88, wherein the second solvent comprises ethanol.

[0275] Embodiment 90 is the method of any one of embodiments 58-89, wherein the genipin, first film-forming agent, and second solvent are present in the second solution in a ratio of genipin:film-forming agent:second solvent of about 57:16:177 to about 57:4:189.

[0276] Embodiment 91 is the method of any one of embodiments 58-90, wherein the genipin, the first film-forming agent, and the second solvent are present in the second solution in a ratio of about 57:8:185 genipin:film-forming agent:second solvent.

[0277] Embodiment 92 is the method of any one of embodiments 58 to 91, wherein the first film-forming agent is selected from the group consisting of polymethylsilsesquioxane, trimethylsiloxysilicate, polypropylsilsesquioxane, dimethicone, cyclopentasiloxane, dimethiconol crosspolymer, polysilicone-6, polysilicone-8, polysilicone-11, polysilicone-14, acrylates / C12-22 alkyl methacrylate copolymer, acrylates / polytrimethylsiloxymethacrylate copolymer, polyvinylpyrrolidone / vinyl acetate (VP / VA) copolymer, VP / dimethiconyl acrylate copolymer, polyvinylpyrrolidone / vinyl acetate (VP / VA) ... and / or a combination thereof.

[0278] Embodiment 93 is the method of embodiment 92, wherein the first film-forming agent is polymethylsilsesquioxane.

[0279] Embodiment 94 is the method of any one of embodiments 56 to 93, wherein the first solution and the second solution are present in the ink composition in a ratio of first solution:second solution of about 1:4 to about 1:1.

[0280] Embodiment 95 is the method of any one of embodiments 56 to 94, wherein the first solution and the second solution are present in the ink composition in a ratio of about 1:2 of first solution:second solution.

[0281] Embodiment 96 is the method of any one of embodiments 57 and 60-95, wherein the film-forming agent is present in an amount of from about 1% to about 10% w / w of the ink composition.

[0282] Embodiment 97 is the method of any one of embodiments 57 and 60-96, wherein the film-forming agent is present in an amount of from about 2% to about 6% w / w of the ink composition.

[0283] Embodiment 98 is the method of any one of embodiments 57 and 60-97, wherein the film-forming agent comprises a volatile silicone resin, polyvinylpyrrolidone, acrylate, acrylamide, copolymer, isododecane resin, or a combination thereof.

[0284] Embodiment 99 is the method of any one of embodiments 57 and 60-98, wherein the film former is selected from the group consisting of polymethylsilsesquioxane, trimethylsiloxysilicate, polypropylsilsesquioxane, dimethicone, cyclopentasiloxane, dimethiconol crosspolymer, polysilicone-6, polysilicone-8, polysilicone-11, polysilicone-14, acrylates / C12-22 alkyl methacrylate copolymer, acrylates / polytrimethylsiloxymethacrylate copolymer, polyvinylpyrrolidone / vinyl acetate (VP / VA) copolymer, VP / dimethiconyl acrylate copolymer, polyvinylpyrrolidone / vinyl acetate (VP / VA) ... and / or a combination thereof.

[0285] Embodiment 100 is the method of any one of embodiments 57 and 60-99, wherein the film-forming agent is selected from the group consisting of polymethylsilsesquioxane, acrylates / C12-22 alkyl methacrylate copolymer, and combinations thereof.

[0286] Embodiment 101 is the method of any one of embodiments 59 to 95, wherein the second film-forming agent is present in an amount of from about 1% to about 5% w / w of the ink composition.

[0287] Embodiment 102 is the method of any one of embodiments 59 to 101, wherein the second film-forming agent is present in an amount of about 3% w / w of the ink composition.

[0288] Embodiment 103 is the method of any one of embodiments 59 to 102, wherein the second film former is selected from the group consisting of polymethylsilsesquioxane, trimethylsiloxysilicate, polypropylsilsesquioxane, dimethicone, cyclopentasiloxane, dimethiconol crosspolymer, polysilicone-6, polysilicone-8, polysilicone-11, polysilicone-14, acrylates / C12-22 alkyl methacrylate copolymer, acrylates / polytrimethylsiloxymethacrylate copolymer, polyvinylpyrrolidone / vinyl acetate (VP / VA) copolymer, VP / dimethiconyl acrylate copolymer, and the like. and / or a combination thereof.

[0289] Embodiment 104 is the method of any one of embodiments 59-103, wherein the second film-forming agent is an acrylate / C12-22 alkyl methacrylate copolymer.

[0290] Embodiment 105 is the method of any one of embodiments 57 and 59-104, wherein the preservative is present in an amount of from about 0.1% to about 5% w / w of the ink composition.

[0291] Embodiment 106 is the method of any one of embodiments 57 and 59-105, wherein the preservative is present in an amount of about 2% to about 4% w / w of the ink composition.

[0292] Embodiment 107 is the method of any one of embodiments 57 and 59-106, wherein the humectant is present in an amount of about 3% w / w of the ink composition.

[0293] Embodiment 108 is the method of any one of embodiments 57 and 59 to 107, wherein the preservative is ascorbic acid, ascorbate, palmitate, citric acid, benzoate, benzoic acid, propionate, propionic acid, sorbate, sorbic acid, salicylic acid, salicylate, hexa-2,4-dienoic acid, hexa-2,4-dienoate, formaldehyde, formaldehyde-releasing agents, formic acid and its salts, 3-acetyl-6-methylpyran-2,4-(3H)-dione and its salts, 3,3'-dibromo-4,4'-hexamethylenedioxydibenzamidine and its salts, thiomersal, phenylmercury salts, undec-10-enoic acid and its salts, 1,3-bis(2-methyl-2-propanol)-2,4-dione ... (2-Ethylhexyl)hexahydro-5-methyl-5-pyrimidine, 5-bromo-5-nitro-1,3-dioxane, bronopol, 2,4-dichlorobenzyl alcohol, 1-(4-chlorophenyl)-3-(3,4-dichlorophenyl)urea, chlorocresol, chloroxylenol, 5-chloro-2-(2,4-dichlorophenoxy)phenol, N,N"-methylenebis[N'-[3-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]urea], polyaminopropyl biguanide, methenamine, quaternium-15, climbazole, DMDM ​​hydantoin, benzyl alcohol, 1-hydroxy-4-methyl-6-(2,4,4-Trimethylpentyl)-2-pyridone, piroctone olamine, bromochlorophene, o-cymen-5-ol, chlorophene, chloroacetamine, methylchloroisothiazolinone, methylisothiazolinone, phenoxyisopropanol, chlorhexidine, chlorhexidine diacetate, chlorhexidine digluconate, chlorhexidine dihydrochloride, dimethyloxazolidine, behentrimonium chloride, cetrimonium bromide, cetrimonium chloride, laurtrimonium bromide, laurtrimonium chloride, steartrimonium bromide, steartrimonium chloride, diazolidinyl urea, hexamidine, hexamidine diisethionate, hexamidine paraben, glutaral, 7-ethylbicyclooxazolidine, chlorphenesin, sodium hydroxymethylglycine, silver chloride, salt Benzethonium chloride, benzalkonium chloride, benzalkonium bromide, benzalkonium saccharinate, benzyl hemiformal, iodopropynyl butylcarbamate, biphenyl-2-ol and its salts, zinc pyrithione, erythorbate, nitrous acid, ethylenediaminetetraacetic acid (EDTA), butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), caprylic acid, dilauryl thiodipropionate, erythorbic acid, guaiac butter, methylparaben, sulfite, bisulfite, metabisulfite, propylparaben, stannous chloride, sulfur dioxide, thiodipropionic acid, isothiazolinone, parabens, phenoxyethanol, ethylhexylglycerin, glycol, tocopherol, 1,2-hexanediol, or combinations thereof.

[0294] Embodiment 109 is the method of any one of embodiments 57 and 59-108, wherein the preservative comprises a combination of phenoxyethanol and ethylhexylglycerin.

[0295] Embodiment 110 is the method of any one of embodiments 57 and 59-109, wherein the phenoxyethanol and ethylhexylglycerin are present in the composition in a ratio of about 9:1 phenoxyethanol:ethylhexylglycerin.

[0296] Embodiment 111 is the method of any one of embodiments 57 and 59-110, wherein the combination of phenoxyethanol and ethylhexylglycerin is present in an amount of from about 0.1% to about 2% w / w of the ink composition.

[0297] Embodiment 112 is the method of any one of embodiments 57 and 59-111, wherein the combination of phenoxyethanol and ethylhexylglycerin is present in an amount of about 1% w / w of the ink composition.

[0298] Embodiment 113 is the method of any one of embodiments 57 and 59-112, wherein the preservative comprises 1,2 hexanediol.

[0299] Embodiment 114 is the method of any one of embodiments 57 and 59-113, wherein the 1,2 hexanediol is present in an amount from about 1% to about 3% w / w of the ink composition.

[0300] Embodiment 115 is the method of any one of embodiments 57 and 59-114, wherein the 1,2 hexanediol is present in an amount of about 2% w / w of the ink composition.

[0301] Embodiment 116 is an ink composition prepared by the method of any one of embodiments 56-115.

[0302] While the present invention has been described in conjunction with a detailed description thereof, it should be understood that the foregoing description is illustrative and is not intended to limit the scope of the invention, which is defined by the scope of the appended claims. Other aspects, advantages, and modifications are within the scope of the following claims.

Claims

1. Semi-permanent colorants and a solvent; a film-forming agent; and a tattooing composition for application to skin, comprising: The semi-permanent colorant is a colorant that penetrates one or more layers of the skin and cannot be removed from the skin without physical destruction or natural desquamation of the skin; A composition wherein the film-forming agent is a combination of an acrylate copolymer, polyvinylpyrrolidone, and a styrene / acrylate copolymer.

2. 10. The composition of claim 1, wherein the semi-permanent colorant is present in an amount of 5% to 15% w / w of the composition.

3. 3. The composition of claim 1, wherein the semi-permanent coloring agent is genipin.

4. A composition according to any one of claims 1 to 3, wherein the solvent is present in an amount of from 65% to 85% w / w of the composition.

5. The composition of any one of claims 1 to 4, wherein the solvent comprises water, methanol, ethanol, isopropanol, diethylene glycol monoethyl ether, or a combination thereof.

6. the solvent comprises water in an amount of 25% to 35% w / w of the composition; and / or 6. The composition of any one of claims 1 to 5, wherein the solvent comprises ethanol in an amount of 40% to 55% w / w of the composition.

7. A composition according to any preceding claim, wherein the film-forming agent is present in an amount of from 5% to 10% w / w of the composition.

8. the acrylate copolymer is present in an amount of 0.1% to 10% w / w of the composition; and / or the polyvinylpyrrolidone is present in an amount of 0.1% to 10% w / w of the composition; and / or A composition according to any preceding claim, wherein the styrene / acrylate copolymer is present in an amount of from 0.1% to 10% w / w of the composition.

9. The composition of any one of claims 1 to 8, wherein the composition further comprises a moisturizer.

10. The composition of any one of claims 1 to 9, wherein the composition further comprises a preservative.

11. 11. The composition of claim 10, wherein the preservative comprises a combination of phenoxyethanol and ethylhexylglycerin.

12. 12. The composition of claim 10, wherein the preservative comprises EDTA.

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