WO2017004100A1 - Encapsulated particles comprising nicotinamide riboside - Google Patents

Encapsulated particles comprising nicotinamide riboside Download PDF

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Publication number
WO2017004100A1
WO2017004100A1 PCT/US2016/039924 US2016039924W WO2017004100A1 WO 2017004100 A1 WO2017004100 A1 WO 2017004100A1 US 2016039924 W US2016039924 W US 2016039924W WO 2017004100 A1 WO2017004100 A1 WO 2017004100A1
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WIPO (PCT)
Prior art keywords
skin care
care agent
core
stable skin
encapsulated
Prior art date
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PCT/US2016/039924
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English (en)
French (fr)
Inventor
Jiten Odhavji Dihora
Taotao Zhu
Todd Laurence Underiner
Jesus Velazquez
Jessica Elizabeth LEON
Original Assignee
The Procter & Gamble Company
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Publication of WO2017004100A1 publication Critical patent/WO2017004100A1/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/602—Glycosides, e.g. rutin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0241—Containing particulates characterized by their shape and/or structure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0241—Containing particulates characterized by their shape and/or structure
    • A61K8/025—Explicitly spheroidal or spherical shape
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0241—Containing particulates characterized by their shape and/or structure
    • A61K8/0283—Matrix particles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/11—Encapsulated compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/25—Silicon; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/26—Aluminium; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • A61K8/673—Vitamin B group
    • A61K8/675—Vitamin B3 or vitamin B3 active, e.g. nicotinamide, nicotinic acid, nicotinyl aldehyde
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/413—Nanosized, i.e. having sizes below 100 nm
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers

Definitions

  • the present disclosure is directed generally to an encapsulated cosmetic agent. More specifically, the present disclosure is directed to encapsulated nicotinamide riboside particles for use as a skin care agent.
  • Skin conditions include some of the most common disorders treated in the developing world, and treating such conditions has led to a booming skin care industry that generates billions of dollars in sales each year.
  • Different skin conditions are associated with widely varied triggers, biological mechanisms, environmental factors, and clinical manifestations.
  • intrinsic factors related to the biochemical changes within the skin typically result in visible signs of skin aging such as wrinkling and other forms of roughness (including increased pore size, flaking and skin lines) and/or uneven skin pigmentation (e.g., age spots or melasma).
  • lifestyle choices and exposure to the environment may allow extrinsic factors such as ultraviolet radiation, pollution (e.g., engine exhaust, cigarette smoke, smog), wind, heat, low humidity, harsh surfactants, abrasives, and the like to damage the skin, leading to undesirable skin appearance.
  • pollution e.g., engine exhaust, cigarette smoke, smog
  • wind heat
  • low humidity e.g., low humidity
  • harsh surfactants e.g., abrasives, and the like
  • a multitude of cosmetic skin care products have been developed that contain skin care agents tailored to treat common skin conditions.
  • Vitamin B 3 compounds such as niacin and its derivatives.
  • U.S. Pat. No. 4,096,240 refers to niacin as effective in skin lightening.
  • U.S. Patent No. 8,106,184 discloses treating skin or epithelial cells with a nicotinoyl riboside or derivative compound that increases the level of intracellular nicotinamide adenine dinucleotide NAD+ to treat skin afflictions or skin conditions such as disorders or diseases associated with or caused by inflammation, sun damage or natural aging.
  • 2005/0267023 discloses methods and compositions for modulating the life span of a cell or its resistance to stress, for example, by contacting the cell with nicotinamide riboside to stimulate the NAD+ salvage pathway in the cell.
  • PCT Pub. No. WO 2015/066382 (“Deren-Lewis”) relates to methods of using nicotinamide riboside to promote the increase of intracellular levels of (NAD+) in cells and tissues for improving cell and tissue survival.
  • Deren- Lewis discloses the use of topical nicotinamide riboside compositions for treating a variety of skin conditions by modulating the NAD+ pathway.
  • NR nicotinamide riboside
  • Many cosmetic compositions include water, and NR tends to hydrolyze in the presence of water. The rate and amount of hydrolysis depends on the amount of water present, the length of time the NR is exposed to the water and the temperature. See, "Kinetic a-Deuterium Isotope Effects for Enzymatic and Nonenzymatic Hydrolysis of Nicotinamide- -Riboside” by Ferraz, et al., Department of Chemistry, Indiana University, Archives of Biochemistry and Biophysics, Vol. 191, No. 2, pp. 431-436, 1978.
  • the NR may be substantially degraded or no longer present.
  • US 2012/0015004 (“Mironov”) relates to encapsulated nutrient salts for use in high-acid beverages.
  • Mironov does not recognize the skin care benefits that NR can provide, nor that NR hydrolyses when incorporated into an aqueous compositions.
  • the stable encapsulated skin care agent comprises a plurality of encapsulated NR particles.
  • Each particle includes a core surrounded by a shell, wherein the core comprises nicotinamide riboside (NR) and shell comprises an encapsulation agent.
  • the encapsulation agent is water impermeable and/or water insoluble, such that the NR contained in the core is not hydrolyzed by any water present in the surrounding environment.
  • the encapsulated particles may include multiple shells and/or cores.
  • the encapsulated particles herein may be made by applying a water insoluble encapsulating agent to a plurality of NR particles using a fluidized bed coater.
  • FIG. 1 is an illustration an encapsulated particle in a single-core, single-shell configuration.
  • FIG. 2 is an illustration of an encapsulated particle in a single-core, multiple-shell configuration.
  • FIG. 3 is an illustration of an encapsulated particle in a multiple-core, single-shell configuration.
  • compositions herein can comprise, consist essentially of, or consist of, the essential components as well as optional ingredients described herein.
  • consisting essentially of means that the composition or component may include additional ingredients, but only if the additional ingredients do not materially alter the basic and novel characteristics of the claimed compositions or methods.
  • the singular forms "a,” “an,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise.
  • Apply or “application”, as used in reference to a composition, means to apply or spread the compositions of the present invention onto a human skin surface such as the epidermis.
  • Aqueous composition refers to a composition that contains at least 20% water.
  • Cosmetic means providing a desired visual effect on an area of the human body.
  • the visual cosmetic effect may be temporary, semi-permanent, or permanent.
  • Cosmetic agent means any substance, as well any component thereof, intended to be rubbed, poured, sprinkled, sprayed, introduced into, or otherwise applied to a mammalian body or any part thereof to provide a cosmetic effect.
  • Cosmetic agents may include substances that are Generally Recognized as Safe (“GRAS”) by the U.S. Food and Drug Administration, food additives, and materials used in non-cosmetic consumer products including over-the-counter medications.
  • the compositions herein may optionally include one or more cosmetic agents in addition to nicotinamide riboside.
  • cosmetic agents may be incorporated in a cosmetic composition comprising a dermatologically acceptable carrier suitable for topical application to skin.
  • Effective amount means the amount of encapsulated nicotinamide riboside sufficient to provide the desired skin benefit (e.g., improve the appearance of a hyperpigmented spot) over the course of a treatment period.
  • Encapsulated means that at least 80% of the surface area of a nicotinamide riboside particle is covered by an encapsulating agent. For example, at least 85%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97, 98%, 99%, and ideally 100% of the surface area of an encapsulated NR particle is covered by an encapsulating agent.
  • Water impermeable refers to a material through which water and other fluids cannot pass without catastrophic failure of the material (e.g., rupturing, tearing, breaking, melting, or dissolving).
  • GRAS Generally recognized as safe
  • GRAS refers to a material that complies with Sections 201(s) and 409 of the Federal Food, Drug, and Cosmetic Act, and the U.S. Food and Drug Administration's implementing regulations in 21 CFR 170.3 and 21 CFR 170.30, which require the premarket review and approval by the FDA of any use of a food substance, unless the substance is generally recognized, among qualified experts, as having been adequately shown to be safe under the conditions of its intended use either through scientific procedures or, for a substance used in food before 1958, through experience based on common use in food.
  • Skin care agent means a cosmetic agent for regulating and/or improving a skin condition.
  • Some nonlimiting examples of regulating and/or improving a skin condition include improving skin appearance and/or feel by providing a smoother, more even appearance and/or feel; increasing the thickness of one or more layers of the skin; improving the elasticity or resiliency of the skin; improving the firmness of the skin; reducing the oily, shiny, and/or dull appearance of skin; improving the hydration status or moisturization of the skin; improving the appearance of fine lines and/or wrinkles; improving skin exfoliation or desquamation; plumping the skin; improving skin barrier properties; improving skin tone; reducing the appearance of spots, redness or skin blotches; and/or improving the brightness, radiancy, or translucency of skin.
  • Skin care agents may incorporated in topical compositions for directed application to a target skin area, or incorporated into an ingestible composition such as a beverage and delivered to a target skin portion via the digestive and circulatory systems of the body.
  • “Stable” means that a composition or ingredient retains a desired level of potency for the duration of predetermined expiration period, as defined by generally accepted pharmaceutical or cosmetological protocols (e.g., good manufacturing practices (“GMP”), or as promulgated by various trade conventions such as, for example, the United States Pharmacoepia Convention.
  • GMP good manufacturing practices
  • a stable, encapsulated NR particle may exhibit less than 20% hydrolysis of the NR contained in the core of the particle (e.g., less than 15%, 10%, 5%, 4%, 3%, 2%, or even less than 1%) when placed in an aqueous solution at between 15 and 40 °C + 2 °C (e.g., 16 °C, 18°C, 20 °C, 22 °C, 24 °C, 26 °C, 28 °C, 30 °C, 32 °C, 34 °C, 36 °C, 38 °C, 40 °C, + 2 °C) for at least 1 hour (e.g., at least 2 hours, 5 hours, 8 hours, 12 hours, or even at least 24 hours).
  • the encapsulated skin care agent herein may be stable in an aqueous composition at 15 - 40 °C for more than 1 day, 2 days, 3 days, 4 days, 5 days, 6 days, 7 days or even for more than 2weeks, 1 month, 2 months, 3 months, 4 months, 5 months, or even more than 6 months. Stability may be determined according to the Hydrolysis Test described in more detail below.
  • Treatment period means the length of time and/or frequency that the encapsulated skin care agent is used.
  • the treatment period may be a predetermined length of time and/or frequency, but need not necessarily be so.
  • Water insoluble refers to a material that does not readily dissolve in water (e.g., has a water solubility at 25-50 °C of less than 200 millimoles/liter, less than 100 millimoles/liter, less than 50 millimoles/liter or even less than 10 millimoles/liter).
  • the encapsulated cosmetic agent herein is a stable NR-containing particle.
  • the stable NR-containing particle The stable
  • NR-containing particle includes NR, and any optional additional ingredients, coated with an encapsulating agent to provide encapsulated particles in a core-shell configuration, for example, as illustrated in FIGS. 1, 2 and 3, which are described in more detail below.
  • the shell may be 5% to 80% (e.g., 10% to 40%) of the weight of the particle and have a total shell thickness of 10 nanometers ("nm") to 1 millimeter (“mm”) (e.g., between 10 nm and 500 micrometers ("um”), 20 nm and 300 ⁇ , 50 nm and 200 ⁇ , 100 nm and 100 ⁇ , 200 nm and 1 ⁇ , 300 nm and 500 nm, or even between 300 nm and 400 nm).
  • the core may include 1 % to 99% NR based on the weight of the particle.
  • the encapsulated particles herein generally have a weight average particle size of less than 500 microns ( ⁇ ) (e.g., less than 400 um, 300 ⁇ , 250 ⁇ , 200 ⁇ , 150 ⁇ , 100 ⁇ or even less than 50 ⁇ ) but typically larger than 1 ⁇ (e.g., larger than 10 ⁇ , 20 ⁇ , 50 um or even larger than 100 um). Particles larger than 500 um, or even larger than 300 ⁇ , may be unsuitable for use in certain compositions such as beverages because they tend to impart an undesirable gritty texture to the beverage.
  • particles larger than 100 ⁇ may not be suitable for use in topical compositions because they can be harder to suspend in a cosmetic composition leading to a gritty and/or non-homogenous feel.
  • particle sizes less than I ⁇ have a surface area-to- volume ratio that undesirably favors increased hydration of the core relative to larger particles.
  • smaller particles may introduce undesirable processing difficulties and/or safety concerns.
  • a composition containing the present particles such as a beverage
  • Visible particles may be provided by any suitable method known for imparting visibility to particles in a beverage, for example, by including GRAS pigments and/or dyes.
  • FIG. 1 is an illustration of an encapsulated particle 10 that includes a solid spherical core 20 surrounded by an encapsulating shell 30.
  • the shell 30 includes an encapsulating agent and provides a water barrier between the core 20 and the external environment, which prevents or at least inhibits water from hydrolyzing NR in the core and/or in an underlying layer.
  • the barrier may be dissolvable, water insoluble, and/or water impermeable. It may be desirable for the shell 30to completely surround the core 30, as shown in FIG. 1, in order to adequately insulate the water-sensitive NR in the core 20 from contact with any water present in the external environment. But it is to be appreciated that some of the particles herein may have less than 100% of the core covered by the encapsulating agent. It is also to be appreciated that the core 20 can be any shape, as desired.
  • the encapsulated particle may include a shell comprising more than one layer of the same or different materials.
  • the encapsulated particle may comprise a multi-layer shell in which a first, outer layer functions as a water insoluble barrier and a second, inner layer functions to scavenge any water that penetrates the first layer, thereby reducing the amount of water available to hydrolyze the NR in the particle.
  • the encapsulated particle may include multiple dissolvable barrier layers and/or NR-containing layers, for example, to provide an encapsulated particle that releases a desired amount of NR over a predetermined period of time ("controlled release particle").
  • the controlled release particle in this example may include alternating barrier layers and NR-containing layers.
  • FIG. 2 is an illustration of an encapsulated particle 100 with a multi-layer shell 130 surrounding an NR-containing core 120.
  • the NR in the core 120 may be solid (i.e., contains less than 5% liquid), dissolved in a miscible fluid or dispersed in an immiscible fluid.
  • the multilayer shell 130 includes a first, outer layer 132 and a second, inner layer 131. While not shown in FIG. 2, it is to be appreciated that the encapsulated particle 100 may, optionally, include one or more additional layers disposed around the first layer 132 and/or second layer 131.
  • the first layer 132, second layer 131, and optional additional layers may be made from the same or different material and may provide the same or different functions, as desired.
  • Each layer 131, and 132 of the multi-layer shell 130 may have the same or different thickness (e.g., between 1 nm and 500 urn, 10 nm and 300 um, 50 nm and 100 um, 100 nm and 50 um, or even between 200 nm and 1 ⁇ ), as long as the NR in the encapsulated particle 100 is able to provide the desired skin care benefit.
  • thickness e.g., between 1 nm and 500 urn, 10 nm and 300 um, 50 nm and 100 um, 100 nm and 50 um, or even between 200 nm and 1 ⁇
  • the encapsulated particles herein may include multiple cores surrounded by a continuous, unitary shell, for example, as illustrated in FIG. 3.
  • FIG. 3 shows an encapsulated particle 200 that includes multiple NR-containing cores 222 surrounded by a continuous shell 220.
  • Multi-core encapsulated particles like the one illustrated in FIG. 3 may be made using known processing techniques such as prilling, spray chilling, spray drying microfluidics, extrusion and loading a porous carrier.
  • the encapsulated cosmetic agent herein includes a nicotinamide riboside containing core coated with an encapsulating agent. Nicotinamide riboside (CAS No. 1341-23-7) has the formula:
  • nicotinamide riboside includes salts of nicotinamide riboside (e.g., nicotinamide riboside chloride). Nicotinamide riboside may be obtained from ChromaDex, Inc., Irvine, CA.
  • the encapsulated particles herein contain at least I % NR, based on the weight of the particle, but typically less than 90% (e.g., from 5% to 90%, 20% to 70% or even from 40% to 60%).
  • the core may optionally include one or more other ingredients commonly included in cosmetic compositions (e.g., colorants, skin tone agents, skin anti-aging agents, nutritional supplements such as vitamins and minerals, anti-inflammatory agents, sunscreen agents, combinations of these and the like), provided that the additional ingredients do not undesirably alter the skin care benefit provided by the NR.
  • the additional ingredients should be suitable for use in contact with human skin tissue without undue toxicity, incompatibility, instability, allergic response, and the like.
  • the encapsulating agent(s) herein form a barrier around the NR-containing core to provide a suitable barrier between the NR-containing core and the external environment.
  • the shell formed by the encapsulating agent may be frangible or pliable (e.g., a plastic, elastic, or plastoelastic film), as long as the NR in the particle is released as intended. It may be desirable to provide an encapsulating shell that releases the NR when the particle is subjected to the shearing and/or crushing force typically experienced during topical application of a cosmetic composition. Additionally or alternatively, it may be desirable to provide an encapsulating shell that releases the NR when the particle is exposed to one or more conditions typically found in the gastrointestinal tract of a human.
  • Encapsulating agents that may be used herein are not particularly limited and can include any suitable GRAS material that provides a desirable combination of barrier and NR release properties.
  • Some non-limiting examples of encapsulating agents that may be suitable for use herein are chitin and chitosan; cellulose and cellulose derivatives such as cellulose acetate phthalate, hydroxy-propyl methyl cellulose, carboxymethyl cellulose, enteric/aquateric coatings and mixtures thereof; silicates, phosphates, and borates; polyvinyl alcohol; polyvinyl acetate / polyvinyl alcohol blends; polyethylene glycols; linear and branched carbohydrates such as simple sugars (monosaccharides) and mixtures thereof, oligosaccharides (2 - 10 monosaccharide units), and polysaccharides (35 or greater monosaccharide units) and mixtures of these; carbohydrates that have been modified to improve their water resistance properties (e.g., by adding alkyl or aryl functiona
  • the encapsulating agents may optionally include plasticizers such as, for example, sorbitol, polyethylene glycol and polypropylene glycol to help achieve a more homogeneous, impermeable coating.
  • Plasticizers when included in the encapsulating agent may ⁇ be present at from 0.01 % to 10% by weight, based on the weight of particle.
  • the shell may be in the form a discrete, continuous layer of material that surrounds the core, for example, as illustrated in FIGS. 1 and 2.
  • the shell may be in form of a solid matrix in which particles of NR (solid or contained in a liquid) are dispersed or suspended, for example, as illustrated in FIG. 3.
  • the stable skin care agent herein may be made using conventional methods of encapsulating a water soluble active to provide a stable particle for use in an aqueous composition.
  • the encapsulated skin care agent herein may be made by applying one or more coatings of an encapsulating agent to an NR-containing material, it may be desirable to use an encapsulating agent and/or process that hydrolyzes less than 20% of the NR in the core is hydrolyzed during encapsulation.
  • Some non-limiting examples of methods of providing the encapsulated particles herein are coacervation, polycondensation, mterfacial polymerization, emulsion polymerization, solvent evaporation, solvent exchange, lyophilization, nanoprecipitation, spray drying, spray chilling, prilling, extrusion, and fluid bed coating. Additional non-limiting examples of particle formation, encapsulation and/or coating techniques are disclosed in U.S. Pat. Nos. 5,550,119; 7,338,928; 6,790,821; 8,236,715; and 8,945,419; 9,029,083; 9,039,273 and U.S. Publication Nos.
  • NR powder particles can be directly coated with an encapsulation agent using a fiuidized bed coating / drying operation, which results in particles with a solid core.
  • a fiuidized bed coating / drying operation which results in particles with a solid core.
  • a Wurster brand fiuidized bed coater or equivalent may be used to provide a continuous, unbroken coating around NR powder particles.
  • the NR powder is sprayed with a suitable coating material (e.g., an aqueous solution of film forming polymers or a meltable, hydrophobic material that solidifies or crystallizes on the surface of the NR core).
  • the spray-on encapsulation agent may be in the form of a suspension, emulsion or dispersion.
  • the fiuidized bed is operated such that the flux number of the fluid bed is between 3.5 and 7 (e.g., between 3.5 and 5.0) and the Stokes number is greater than 1 (e.g., between 10 and 1000 or between 100 and 1000).
  • the flux number provides and estimation of the operating parameters of a fiuidized bed to control coating within the bed, and the Stokes number is a measure of particle coalescence for describing the degree of mixing occurring to particles in the fluid bed.
  • U.S. Pat. No. 6,790,821 to Wasserman, et al. describes how to determine flux number and Stokes number.
  • the sprayed particles in the fiuidized bed are then dried with dehumidified air maintained below the degradation temperature of the NR.
  • the resulting coated particles may have a weight average particle size of between 20 and 800 microns.
  • the NR may be mixed with inert materials and binders prior to the fiuidized bed process to achieve a particle size that is appropriate for fluidization.
  • particles ⁇ 20 micrometers are typically not appropriate for fluidization, as they tend to elutriate out of the bed), and particles greater than 800 microns are not appropriate for fluidization, as they tend to require undesirably high fluidization velocities.
  • the fluid bed mixer includes at least one coating zone where the encapsulation agent is applied.
  • the coating zone involves the spraying of the encapsulation agent onto the fiuidized particles.
  • the bed may be fiuidized with heated air. Spraying may be achieved via nozzles capable of delivering a fine or atomized spray of the encapsulation agent to achieve complete coverage of the particles.
  • the droplet size from the atomizer is less than 2 times the particle size.
  • This atomization can be achieved either through a conventional two-fluid nozzle with atomizing air, or alternatively by means of a conventional pressure nozzle, it may be desirable to position the nozzle above the fluidized height of the particles in the fluid bed to allow a vertical down spray of the coating mixture (i.e., a top spray configuration).
  • the coating zone of the fluid bed may be followed by a drying zone and a cooling zone. It is to be appreciated that alternative arrangements are also possible to achieve the desired coated particles.
  • Typical conditions within a fluid bed apparatus include: (i) from 1 to 20 minutes of mean residence time; (ii) from 100 to 600 mm of depth of unfluidized bed; (iii) a droplet size of less than 2 times the size of the particles, (e.g., not more than 100 ⁇ or 50 microns); (iv) from 150 to 1600 mm of spray height from the fluid bed plate or preferably 0-600 mm from the top of the fluid bed, (v) from 0.1 to 4.0 m/s of fluidizing velocity, preferably 1.0 to 3.0 m s; and (vi) from 12 to 200 °C of bed temperature (e.g., 15 to 100 °C).
  • the conditions in the fluid bed may vary depending on a variety of known factors.
  • NR powder may be dissolved in a miscible solvent, and droplets of the resulting NR-containing solution can be encapsulated using known chemical or physical encapsulation techniques, resulting in the formation of encapsulated particles with a liquid core.
  • solvents that can dissolve NR are 3 -methyl isoxazole, acetanilide, succinic anhydride, pyridazine, 1 -methyl imidazole, salicylaldehyde, tetrahydrofurfuryl alcohol, 2-pyrolidone, 2-pyrrolidinone, isoxazole, dimethyl sulfone, tetramethylene sulfone, thiazole, thiourea, b-propiolactone, ethylene cyanohydrin, dimethyl sulfoxide, dimethyl sulfoxide, 1,,3-triazole, diethylenetriamine, diethylenetriamine, dimethyl formamide, ⁇ , ⁇ -dimethylforniamide, 2-chloropropenoic acid, acetonecyanhydrin, shellac, polyethylene oxide 4000, sorbitol and mixtures of these.
  • NR powder can be dispersed in an immiscible solvent, and the dispersion can then be encapsulated using chemical or physical encapsulation techniques known in the art for encapsulation of lipophilic oils, resulting in the formation of encapsulated particles with a liquid core.
  • immiscible solvents are mono, di- and tri- esters of C4-C24 fatty acids and glycerin; fatty acid esters of polyglycerol oligomers; poly alphaolef ins, butyl oleate, hydrogenated castor oil, sucrose benzoate, dodecanoic acid, palmitic acid, stearic acid, octadecanoic acid, monoester with 1,2,3-propanetriol; dodecanoic acid, pentyl ester; oclanoic acid, nonyl ester; pentadecanoic acid, ethyl ester; hexadecanoic acid, methyl ester; dodecanoic acid, 4-methylphenyl ester; dodecanoic acid, 3-methylbutyl ester; tetradecanoic acid, 1-methylethyl ester; hexadecanoic acid; 1 -phenanthrenecarboxylic acid
  • an NR- solution e.g., NR dissolved in a miscible liquid
  • a meltable immiscible solvent may be dispersed in a meltable immiscible solvent, which is then prilled or spray chilled to produce encapsulated particles.
  • the melted suspension is dosed onto a centrifugal atomizer.
  • the centrifugal atomizer generates atomized particles that are subsequently cooled in the air.
  • solubilized NR can be pre-loaded into a porous carrier such as zeolites, precipitated silicas or lattice-network microspheres, and then encapsulated according to one of the aforementioned encapsulation techniques.
  • a porous carrier such as zeolites, precipitated silicas or lattice-network microspheres
  • solubilized NR contained in the pores of the porous carrier is protected from hydrolysis by the lattice structure of the carrier and the encapsulation agent, which work cooperatively to hinder hydrolysis of the NR.
  • the NR powder (either dissolved in a miscible solvent or dispersed in an immiscible carrier fluid) can be encapsulated in single or multiple shells using a microfluidic technique.
  • the NR-containing fluid and shell materials/precursors are pushed through a concentric nozzle, then emulsified into drop-in-a-drop (double emulsion) by a continuous phase fluid.
  • additional shell layers can be formed to yield a microcapsule suspension that provides adequate hydrolysis stability to NR when dosed in a finished product formulation.
  • U.S. Publication No. 2008/0213593 discloses microfluidic techniques that may be suitable for use herein.
  • the encapsulated particles herein may be coated with a material to reduce the rate of leakage of NR from the particles when the particles are subjected to a bulk environment (e.g., storage and shipping).
  • a material to reduce the rate of leakage of NR from the particles when the particles are subjected to a bulk environment e.g., storage and shipping.
  • Some non-limiting examples of such materials include polyvinyl pyrrolidone homopolymer, and its various copolymers with styrene, vinyl acetate, imidazole, primary and secondary amine containing monomers, methyl acrylate, polyvinyl acetal, maleic anhydride; polyvinyl alcohol homopolymer, and its various copolymers with vinyl acetate, 2-acrylamide-2-methylpropane sulfonate, primary and secondary amine containing monomers, imidazoles, methyl acrylate; poly aery lamides; poly aery lie acids; microcrystalline waxes; paraffin
  • the encapsulated NR particles herein may be used anywhere stable NR particles are desired.
  • the encapsulated NR particles may be incorporated into a cosmetic composition such as a skin care composition or a beverage to improve the appearance of skin or to treat a skin condition.
  • the Hydrolysis Test provides a method for determining the stability of NR.
  • this method can be used to determine the amount of NR that is hydrolyzed when incorporated into an aqueous composition.
  • a suitable aqueous vehicle i.e., a skin care product or other composition that simulates an aqueous skin care product
  • mix the NR particles into a suitable aqueous vehicle i.e., a skin care product or other composition that simulates an aqueous skin care product
  • Table 1 is provided as an example of ingredients that can be combined to form a suitable aqueous vehicle.
  • the NR particles may be added at any amount desired, but are typically included at from 0.1% to 5% w/v.
  • the ingredients may be combined using conventional methods of making skin care compositions. After the skin care composition is made, weigh 0.1 g of the skin care composition into a polypropylene conical centrifuge tube, and dilute with 25 mL of a diluent.
  • the diluent is made from 5% (v/v) 5 mM ammonium formate, 0.025% (v/v) formic acid in Milli-Q water and 95% (v/v) acetonitrile. Vortex or homogenize as needed to disperse the product formulation in the diluent. Using a syringe, filter a sufficient amount of the sample into an autosampler vial for HPLC analysis as described below. Prepare standard stock solutions in Milli-Q water for calibration. Dilutions are made into diluent to cover a range of approximately 5-350 ⁇ g/mL analyte in solution for calibration curves. Table 1
  • the mobile phase is: (A) 5 mM ammonium formate with 0.025% (v/v) formic acid in Milli-Q water; and (B) a mixture of 95% acetonitrile and 5% mobile phase (A) also with 0.025% (v/v) formic acid. Begin the gradient at 100% (B) and hold for 3 minutes. Next, use 60% (B) until 16 minutes, and hold for 3 minutes before returning to the starting condition of 100% (B). The entire chromatographic run should take about 24 minutes using a flow rate of 1.0 mL/min. Table 2 shows the times and gradients used in the test.
  • the diode array detector is set to scan wavelengths of 205-350 nm. Chromatograms are extracted at 260 nm.
  • Retention time is approximately 12.6 minutes. Quantitation is performed using Chromeleon v.7.2 or equivalent chromatography data system software package. A linear curve fit of the response of the calibration standards is used to determine analyte in solution levels. Results are expressed as weight percent (w/w %) once corrected for the dilution factor and weight of formulation aliquot.

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WO2018237218A1 (en) 2017-06-23 2018-12-27 The Procter & Gamble Company COMPOSITION AND METHOD FOR ENHANCING SKIN APPEARANCE
US11622963B2 (en) 2018-07-03 2023-04-11 The Procter & Gamble Company Method of treating a skin condition
MX2021010043A (es) * 2019-02-21 2022-07-19 Chromadex Inc Uso de nicotinamida ribósido, ácido nicotinico ribósido, compuestos de nicotinil ribósido reducido y derivados de compuestos de nicotinil ribósido en formulaciones.
CN115843238B (zh) 2020-06-01 2025-06-10 宝洁公司 改善维生素b3化合物渗透到皮肤中的方法
US10959933B1 (en) 2020-06-01 2021-03-30 The Procter & Gamble Company Low pH skin care composition and methods of using the same
US20220241305A1 (en) * 2021-01-29 2022-08-04 ChromaDex Inc. Ethyl cellulose based coatings for microencapsulation of nicotinamide riboside, nicotinic acid riboside, reduced nicotinyl riboside compounds, and nicotinyl riboside compound derivatives
CN114577935B (zh) * 2022-03-03 2024-07-23 中科谱研（北京）科技有限公司 一种胶囊中烟酰胺核糖氯化物的分离检测方法

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