US20140086859A1 - Low oil compositions comprising a 4-substituted resorcinol and a high carbon chain ester - Google Patents

Low oil compositions comprising a 4-substituted resorcinol and a high carbon chain ester Download PDF

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Publication number
US20140086859A1
US20140086859A1 US13/624,998 US201213624998A US2014086859A1 US 20140086859 A1 US20140086859 A1 US 20140086859A1 US 201213624998 A US201213624998 A US 201213624998A US 2014086859 A1 US2014086859 A1 US 2014086859A1
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Prior art keywords
composition
skin
ester
compositions
carbon chain
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Abandoned
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US13/624,998
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English (en)
Inventor
Marisa DeVita Dufort
Simarna Kaur
Michael D. Southall
Ping Wen
Jeffrey M. Wu
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Johnson and Johnson Consumer Inc
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Johnson and Johnson Consumer Companies LLC
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Priority to US13/624,998 priority Critical patent/US20140086859A1/en
Assigned to JOHNSON & JOHNSON CONSUMER COMPANIES, INC. reassignment JOHNSON & JOHNSON CONSUMER COMPANIES, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: WU, JEFFREY M., SOUTHALL, MICHAEL D., DUFORT, MARISA DEVITA, KAUR, SIMARNA, WEN, Ping
Priority to CA2827499A priority patent/CA2827499C/en
Priority to AU2013231070A priority patent/AU2013231070B2/en
Priority to EP13185624.7A priority patent/EP2712607B1/en
Priority to ES13185624T priority patent/ES2732215T3/es
Priority to CN201310438957.XA priority patent/CN103705402B/zh
Priority to KR1020130112977A priority patent/KR102122181B1/ko
Priority to BR102013024429A priority patent/BR102013024429B8/pt
Publication of US20140086859A1 publication Critical patent/US20140086859A1/en
Assigned to JOHNSON & JOHNSON CONSUMER INC reassignment JOHNSON & JOHNSON CONSUMER INC MERGER AND CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: JOHNSON & JOHNSON CONSUMER COMPANIES, LLC, JOHNSON & JOHNSON CONSUMER INC.
Assigned to JOHNSON & JOHNSON CONSUMER COMPANIES, LLC reassignment JOHNSON & JOHNSON CONSUMER COMPANIES, LLC MERGER (SEE DOCUMENT FOR DETAILS). Assignors: JOHNSON & JOHNSON CONSUMER COMPANIES, INC.
Assigned to JOHNSON & JOHNSON CONSUMER INC. reassignment JOHNSON & JOHNSON CONSUMER INC. CORRECTIVE ASSIGNMENT TO CORRECT THE MERGED ENTITY' NEW NAME PREVIOUSLY RECORDED AT REEL: 036041 FRAME: 0605. ASSIGNOR(S) HEREBY CONFIRMS THE MERGER & CHANGE OF NAME. Assignors: JOHNSON & JOHNSON CONSUMER COMPANIES, LLC
Priority to US15/251,121 priority patent/US10307352B2/en
Abandoned legal-status Critical Current

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    • 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
    • A61K8/30—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
    • A61K8/347—Phenols
    • 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
    • A61K8/31—Hydrocarbons
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8182—Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • 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
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products 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
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/10—Anti-acne agents
    • 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
    • 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
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/30—Characterized by the absence of a particular group of ingredients
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • 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
    • A61Q5/00—Preparations for care of the hair

Definitions

  • a low oil composition comprising a 4-substituted resorcinol, a high carbon chain ester and a cosmetically acceptable topical carrier is provided.
  • the composition is useful for topical application to the skin.
  • 4-Substituted resorcinols are known to provide anti-aging and lightening benefits to the skin when applied topically. For various reasons, such as cost and formulation integrity it is desirable to reduce the concentration of 4-substituted resorcinols in topical skin products. However, reducing the concentration of 4-substituted resorcinols can also reduce the observed benefit. Accordingly, the inventors have recognized the need for formulations with reduced concentrations of 4-substituted resorcinols. Surprisingly, the inventors have found that low oil compositions that include a high carbon chain ester can be formulated with low concentrations of 4-substituted resorcinols and still provide skin benefits.
  • the invention provides a composition including water, about 0.1% to about 0.4% of a 4-substituted resorcinol, an ester having at least about 25 carbon atoms, and a polymeric emulsifier.
  • the composition comprises less than about 5% by weight of oils and is substantially free of monomeric emulsifier.
  • topically applying means directly laying on or spreading on outer skin, the scalp, or hair, e.g., by use of the hands or an applicator such as a wipe, roller, or spray.
  • cosmetically acceptable means that the ingredients the term describes are suitable for use in contact with tissues (e.g., the skin or hair) without undue toxicity, incompatibility, instability, irritation, allergic response, or the like.
  • compositions of the present invention are suitable for treating signs of skin aging.
  • signs of skin aging includes the presence of lines and wrinkles, loss of elasticity, uneven skin, and blotchiness.
  • the sign of aging is the presence of lines and wrinkles and/or loss of elasticity.
  • treating signs of skin aging refers to mitigating, reducing, preventing, improving, or eliminating the presence or signs of skin aging described above.
  • wrinkle includes fine lines, fine wrinkles, or coarse wrinkles.
  • wrinkles include, but are not limited to, fine lines around the eyes (e.g., “crow's feet”), forehead and cheek wrinkles, frown-lines, and laugh-lines around the mouth.
  • loss of elasticity includes loss of elasticity or structural integrity of the skin or tissue, including but not limited to sagging, lax and loose tissue.
  • the loss of elasticity or tissue structure integrity may be a result of a number of factors, including but not limited to disease, aging, hormonal changes, mechanical trauma, environmental damage, or the result of an application of products, such as a cosmetics or pharmaceuticals, to the tissue.
  • “uneven skin” means a condition of the skin associated with diffuse or mottled pigmentation, which may be classified as hyperpigmentation, such as post-inflammatory hyperpigmentation.
  • blotchiness means a condition of the skin associated with redness or erythema.
  • compositions of the present invention are suitable for treating acne.
  • treating acne refers to a mitigating, reducing, preventing, improving, or eliminating the presence or signs of disorders resulting from the actions of hormones and other substances on the sebaceous glands and hair follicles, typically leading to clogged pores and the formation of lesions on the skin.
  • cosmetic refers to a beautifying substance or preparation which preserves, restores, bestows, simulates, or enhances the appearance of bodily beauty or appears to enhance the beauty or youthfulness, specifically as it relates to the appearance of tissue or skin.
  • the term “lightening the skin” refers generally to lightening, brightening, whitening, and/or evening of the skin tone, skin color, and/or shade of skin, and/or to the reduction in sallowness, and/or to the lightening and/or fading of hyperpigmented marks and/or lesions including, but not limited to, pigmented spots, melanin spots, age spots, sun spots, senile lentigos, freckles, lentigos simplex, pigmented solar keratosis, seborrhoeic keratosis, melasma, acne marks, post-inflammatory hyperpigmentation, lentigines, ephelides, combinations of two or more thereof and the like.
  • “lightening the skin” also refers to increased skin radiance, glow, translucency and/or luminescence and/or obtaining a more radiant, glowing, translucent or luminous skin tone appearance or a less yellow or sallow skin tone. In certain preferred embodiments, “lightening the skin” refers to lightening and evening the skin tone, increasing skin radiance and/or lightening age spots.
  • skin in need of skin lightening treatment refers generally to skin that exhibits one or more property selected from the group consisting of: skin having a measured Individual Typology Angle (ITA) value below 41 as determined per the COLIPA GUIDELINE: GUIDELINE FOR THE COLORIMETRIC DETERMINATION OF SKIN COLOUR TYPING AND PREDICTION OF THE MINIMAL ERYTHEMAL DOSE (MED) WITHOUT UV EXPOSURE published in 2007, which is incorporated herein by reference and further described below, darkened and/or sallow skin, including skin darkened by UV, skin with uneven skin tone, or skin with one or more hyperpigmented marks and/or lesions including, but not limited to, pigmented spots, melanin spots, age spots, sun spots, senile lentigos, freckles, lentigos simplex, pigmented solar keratosis, seborrhoeic keratosis, melasma, acne marks, post-inflammatory hyperpig
  • ITA Individual Typology Angle
  • skin color is defined function of the ITA value as: very light skin >55; Light skin 41-55, Intermediate 28-41, and Tan skin ⁇ 28.
  • skin in need of skin lightening refers to individuals with a skin having an ITA value of less than 41, such as about 40 or less, about 35 or less, about 30 or less, or more preferably about 28 or less.
  • the present invention is directed to compositions and methods for use on skin in need of skin lightening treatment selected from sallow and/or darkened skin.
  • the present invention is directed to compositions and methods for use on skin in need of skin lightening treatment selected from the group consisting of age spots, freckles, marks left after acne, and combinations of two or more thereof.
  • Compositions of the present invention comprise a 4-substituted resorcinol.
  • 4-Substituted resorcinols have the chemical structure of resorcinol but include a substitution at the 4 position.
  • Suitable 4-substituted resorcinols include those having alkyl, aryl, alkenyl, or alkynyl substitutions.
  • the 4-substituted resorcinol comprises a C4-C10 substitution. In certain embodiments the other positions may be substituted or unsubstituted.
  • the 4-substituted resorcinol is 4-hexyl resorcinol, which has the following structure:
  • 4-hexyl resorcinol is commercially available, for example, as “SYNOVEA HR” from Sytheon of Lincoln Park, N.J.
  • compositions according to invention comprising low levels of 4-substituted resorcinols provide surprisingly good efficacy for skin benefits such as anti-aging, anti-acne, and lightening benefits.
  • the compositions comprise about 0.1% to about 0.4% by weight of 4-substituted resorcinol.
  • the compositions comprise about 0.2% to about 0.4%, such as from about 0.3% to about 0.4%, by weight of 4-substituted resorcinol.
  • One or more than one 4-substituted resorcinol may be used.
  • compositions of the present invention include a high carbon chain ester, i.e., an ester having at least about 25 carbon atoms.
  • a high carbon chain ester i.e., an ester having at least about 25 carbon atoms.
  • the inventors have found that inclusion of a high carbon chain ester in the compositions tends to improve dramatically the activity of 4-substituted resorcinol.
  • Suitable high carbon chain esters are generally hydrophobic and include those having, for example from 25 to about 100 carbon atoms, such as those having from 25 to about 75 carbon atoms, such as those having from 25 to about 50 carbon atoms, such as those having from 25 to 37 carbon atoms.
  • One or more than one high carbon chain ester may be used.
  • the high carbon chain ester is branched.
  • the high carbon chain ester is a liquid at room temperature and atmospheric pressure and may have a melting point less than 30° C., such as less than 25° C.
  • the high carbon chain ester has from one to four ester groups.
  • the high carbon chain ester is desirably non-ionic and free of hydrophilic moieties (e.g., anionic, cationic, zwitterionic, or nonionic groups that are polar, including sulfate, sulfonate, carboxylate, phosphate, phosphonates, ammonium, including mono-, di-, and trialkylammonium species, pyridinium, imidazolinium, amidinium, poly(ethyleneiminium), ammonioalkylsulfonate, ammonioalkylcarboxylate, amphoacetate, hydroxyl, and poly(ethyleneoxy)sulfonyl) that would otherwise tend to render the ester amphiphilic.
  • hydrophilic moieties e.g., anionic, cationic, zwitterionic, or nonionic groups that are polar, including sulfate, sulfonate, carboxylate, phosphate, phosphonates, ammonium, including mono-,
  • the high carbon chain ester is desirably composed of only hydrogen, carbon, and oxygen atoms and may be free of ether functional groups.
  • suitable high carbon chain esters include octyldodecyl neopentanoate, a C25 ester that is commercially available as ELEFAC I-205 from Alzo International Inc. of Sayerville, N.J.; and pentaerythritol tetraethylhexanoate, a C37 ester that is commercially available as DUB PTO also from Alzo International Inc. of Sayerville, N.J.
  • the amount of the high carbon chain ester in the composition may range, for example, from about 0.1% to about 5% by weight of the composition. In certain embodiments the high carbon chain ester is present in an amount of about 0.1% to about 3%, such as from about 1% to about 3%, by weight of the composition.
  • compositions of the present invention include a polymeric emulsifier (i.e., having one or more definable repeat unit).
  • the repeat unit is other than oxyalkylene (—C n O—) where n is from 1 to 5.
  • the polymeric emulsifier is suitable for emulsifying discrete oil-phase droplets in a continuous water phase or vice-versa.
  • a mixture that is visibly homogeneous results when 0.25% to 2% by weight of the polymeric emulsifier is mixed, either lightly or vigorously, with 1% by weight mineral oil in either pure deionized water or deionized water whose pH has been adjusted into the range of 5-10 with either HCl or NaOH.
  • visibly homogeneous it is meant that the mixture is rendered phase stable by preventing any evident “layering,” flotation, or visible phase separation at room temperature and pressure for a period of at least one week and preferably at least one month.
  • Polymeric emulsifiers useful in the present invention may have a weight average molecular weight that is greater than about 1000 daltons, such as greater than about 5000 daltons. In certain cases, polymeric emulsifiers useful in the present invention are fully cross-linked and therefore have an infinite molecular weight.
  • Polymeric emulsifiers include, for example, hydrophobically-modified, crosslinked, anionic acrylic copolymers, including random polymers, but may also exist in other forms such as block, star, graft, and the like.
  • the hydrophobically modified, crosslinked, anionic acrylic copolymer may be synthesized from at least one acidic monomer and at least one hydrophobic ethylenically unsaturated monomer.
  • suitable acidic monomers include those ethylenically unsaturated acid monomers that may be neutralized by a base.
  • suitable hydrophobic ethylenically unsaturated monomers include those that contain a hydrophobic chain having a carbon chain length of at least about 3 carbon atoms.
  • An example of a suitable hydrophobically modified acrylic polymer is an acrylates/C10-30 alkyl acrylate crosspolymer, such as PEMULEN TR-1 available from Lubrizol Corporation of Ohio.
  • the polymeric emulsifier is a water-soluble or water-swellable copolymer based on acrylamidoalkyl sulfonic acid and cyclic N-vinylcarboxamides such as commercially available ARISTOFLEX® AVC by Clariant Corporation; a water-soluble or water-swellable copolymer based on acrylamidoalkyl sulfonic acid and hydrophobically modified methacrylic acid such as commercially available ARISTOFLEX® HMB by Clariant Corporation; or a homopolymer of acrylamidoalkyl sulfonic acid such as commercially available Granthix APP by Grant Industries, Inc.
  • the polymeric emulsifier is an ethylcellulose polymer.
  • the amount of polymeric emulsifier in the composition may range, for example, from about 0.1% to about 5% by weight of the composition. In certain embodiments, the amount of polymeric emulsifier is about 0.25% to about 3%, such as from about 0.5% to about 1%, by weight of the composition. One or more than one polymeric emulsifier may be used.
  • compositions of the present invention include a high carbon chain ester, they are nevertheless low oil compositions.
  • low oil it is meant that the amount of oils in the composition is not excessive; in particular the total amount of oils (inclusive of the high carbon chain ester) in the composition is less than about 5% by weight of the composition.
  • oils means hydrophobic compounds including hydrocarbon oils such as mineral oils, petrolatum, vegetable oils (e.g. triglycerides such as caprylic/capric triglyceride), and other mixtures of fatty esters, including but not limited to esters of glycerol, and high viscosity silicone oils such as those having 6 or more alkylsiloxy groups in sequence and/or those silicone oils having a viscosity of 350 centistokes or more at standard temperature and pressure.
  • hydrocarbon oils such as mineral oils, petrolatum, vegetable oils (e.g. triglycerides such as caprylic/capric triglyceride), and other mixtures of fatty esters, including but not limited to esters of glycerol, and high viscosity silicone oils such as those having 6 or more alkylsiloxy groups in sequence and/or those silicone oils having a viscosity of 350 centistokes or more at standard temperature and pressure.
  • Hydrocarbon oils have a carbon chain length of at least eight, and in certain embodiments at least eleven, in which none of the carbons is a carbonyl carbon or has a hydrophilic moiety (described above with respect to the high carbon chain ester) bonded directly to it. Also encompassed in the definition of oils are compounds that meet the requirements described above and are solid at room temperature (often called “waxes”). “Oil” as described herein does not encompass those compounds having a carbon chain that requires aromatic groups to achieve the limit of at least eight or at least eleven carbons.
  • Compositions of the present invention are substantially free of monomeric emulsifiers.
  • Monomeric emulsifiers are non-polymeric compounds suitable for emulsifying discrete oil-phase droplets in a continuous water phase or vice-versa. Specifically, monomeric emulsifiers are able to render a mixture of 1% by weight mineral oil in pure deionized water phase stable. Monomeric emulsifiers may have a molecular weight that is less than 5000 daltons, such as less than 1000 daltons.
  • Common monomeric emulsifiers are amphiphilic molecules and may be anionic, non-ionic, cationic, or amphoteric.
  • Anionic emulsifiers include particular molecules of various chemical classes, for example, alkyl sulfates, alkyl ether sulfates, alkyl monoglyceryl ether sulfates, alkyl sulfonates, alkylaryl sulfonates, alkyl sulfosuccinates, alkyl ether sulfosuccinates, alkyl sulfosuccinamates, alkyl amidosulfosuccinates, alkyl carboxylates, alkyl amidoethercarboxylates, alkyl succinates, fatty acyl sarcosinates, fatty acyl amino acids, fatty acyl taurates, fatty alkyl sulfoacetates, alkyl phosphates.
  • Nonionic emulsifiers may include, for example, amide ethoxylates, monoglyceride ethoxylates, sorbitan ester ethoxylates alkyl polyglycosides, mixtures thereof, and the like.
  • Certain other notable nonionic emulsifiers include polyoxyethylene derivatives of polyol esters, wherein the polyoxyethylene derivative of polyol ester (1) is derived from (a) a fatty acid containing from about 8 to about 22, such as from about 10 to about 14 carbon atoms, and (b) a polyol selected from sorbitol, sorbitan, glucose, ⁇ -methyl glucoside, polyglucose having an average of about 1 to about 3 glucose residues per molecule, glycerine, pentaerythritol and mixtures thereof, (2) contains an average of from about 10 to about 120, such as about 20 to about 80 oxyethylene units; and (3) has an average of about 1 to about 3 fatty acid residues per mole of polyoxyethylene derivative of polyol ester, alkyl glucosides or polyglucosides, which are the condensation products of (a) a long chain alcohol containing from about 6 to about 22, such as from about 8 to about 14 carbon atoms, with (b
  • Amphoteric emulsifiers may include 1) molecules that contain both acidic and basic sites such as, for example, an amino acid containing both amino (basic) and acid (e.g., carboxylic acid, acidic) functional groups; or 2) zwitterionic molecules which possess both positive and negative charges within the same molecule. The charges of the latter may be either dependent on or independent of the pH of the composition. Examples of zwitterionic materials include, but are not limited to, alkyl betaines and amidoalkyl betaines. The amphoteric surfactants are disclosed herein without a counter ion.
  • amphoteric surfactants are either electrically neutral by virtue of having balancing positive and negative charges, or they have counter ions such as alkali metal, alkaline earth, or ammonium counter ions, amphocarboxylates such as alkylamphoacetates (mono or di); alkyl betaines; amidoalkyl betaines; amidoalkyl sultaines; amphophosphates; phosphorylated imidazolines such as phosphobetaines and pyrophosphobetaines; carboxyalkyl alkyl polyamines; alkylimino-dipropionates; alkylamphoglycinates (mono or di); alkylamphoproprionates (mono or di),); N-alkyl ⁇ -aminoproprionic acids; alkylpolyamino carboxylates.
  • Cationic emulsifiers include may include alkyl quaternaries (mono, di, or tri), benzyl quaternaries, ester quaternaries, ethoxylated quaternaries, alkyl amines, and the like.
  • substantially free of monomeric emulsifier means the amount of monomeric emulsifier in the composition is insufficient to render the composition phase stable were any polymeric emulsifier removed from the composition and replaced with water. In certain other embodiments the amount of monomeric emulsifier is less than about 1% by weight of the composition. In certain other embodiments, the amount of monomeric emulsifier is less than the amount of polymeric emulsifier in the composition. In other embodiments, the composition is free of monomeric emulsifier.
  • the composition also includes water. In one embodiment, the composition comprises at least about 70% by weight of water.
  • the composition is applied topically to human skin and/or hair.
  • the composition may further include other ingredients that may comprise about 50% to about 99.99%, by weight, of the composition (e.g., from about 80% to about 99.9%, by weight, of the composition), such as humectants, chelating agents (e.g., EDTA), pH adjusters (e.g., citric acid, sodium hydroxide), preservatives (e.g., chlorphenesin), texture aids/skin conditioners (e.g., starch polymers, cationics, and the like), low viscosity organosiloxanes, additional skin benefit agents and the like.
  • humectants e.g., from about 80% to about 99.9%, by weight, of the composition
  • chelating agents e.g., EDTA
  • pH adjusters e.g., citric acid, sodium hydroxide
  • preservatives e.g., chlorphenesin
  • the humectants may be present in an amount of about 1% to about 20%, such as from about 2% to about 12%, such as from about 3% to about 10%, by weight of the composition.
  • Suitable low viscosity organosiloxanes include low viscosity dimethicone and other silicones having about 5 or less alkylsiloxy groups in sequence. Examples include DC 200 Fluid, 50 cst and DC 2-1184 from Dow Corning.
  • the composition further contains a skin benefit agent other than 4-substituted resorcinol.
  • a skin benefit agent is a compound (e.g., a synthetic compound or a compound isolated from a natural source or a natural extract) that has a cosmetic or therapeutic effect on the skin or hair, including, but not limiting to, anti-acne agents, anti-inflammatory agents external analgesics, sunscreens, antioxidants, keratolytic agents, vitamins (e.g., Vitamin D, vitamin B, Vitamin A), anti-aging actives (including skin firming agents, collagen promoters, elastin promoters, skin lighteners, and the like).
  • the additional skin benefit agent will typically be present in the composition in an amount of about 0.001% to about 20% by weight of the composition, e.g., about 0.005% to about 10% such as about 0.01% to about 5% by weight of the composition.
  • compositions of the present invention may be prepared using methodology that is well known by an artisan of ordinary skill.
  • compositions of the present invention may be topically applied to mammalian skin.
  • the skin is in need of treatment for one or more signs of skin aging as described above.
  • the compositions are applied to skin in need of treatment for lines and wrinkles and/or loss of elasticity.
  • the compositions may be applied to the skin in need of such treatment according to a suitable treatment regimen, e.g., from as much as, twice per day to as little as once every three days or so.
  • compositions of the present invention may also be useful for treating other need states associated with skin.
  • compositions of the present invention may be useful for treating post-inflammatory hyperpigmentation, for reducing pore size, for reducing sebum production, and for scar mitigation.
  • Composition 1 was prepared using 4-hexyl resorcinol, octyldodecyl neopentanoate, a high carbon chain ester, and the other components in Table 1 as follows.
  • PEMULEN TR-1 is available from Lubrizol of Wickliffe, Ohio.
  • OLIVEM TR-1 is available from B&T SrI of Arcore, Italy.
  • ARISTOFLEX AVC is available from Clariant Corporation Charlotte, N.C.
  • EUXYL PE 9010 is available from Schulke & Mayr GmbH of Norderstedt, Germany.
  • DC 200 Fluid and DC 2-1184 are available from Dow Corning of Midland, Mich. Advanced Moisture Complex w and Vitamin D3 are available from BASF of Ludwigshafen, Germany.
  • NAB Mushroom PF is available from Arch Lonza of Basel, Switzerland.
  • Paraoil Flaxseed Oil is available from Paradigm Science: Benxi, China.
  • SYNOVEA HR is available from Sytheon of Lincoln Park, N.J.
  • COVSAT is available from Vivimed labs LTD of Bonthapally Village, India.
  • DRY-FLO PURE is available from AkzoNobel of Chicago, Ill.
  • VERSENE NA is available from Dow Chemical of Midland, Mich.
  • ELEFAC I-205 is octyldodecyl neopentanoate, a C25 ester that is commercially available from Alzo International Inc. of Sayerville, N.J.
  • compositions were prepared by changing the amount of octyldodecyl neopentanoate and adjusting with water, or replacing the octyldodecyl neopentanoate with a different ester.
  • the compositions are listed in Table 2.
  • Compositions 2-6 were according to the invention (Compositions 3 and 4 both contained 3% octyldodecyl neopentanoate). Comparative Compositions C1-C4 did not contain a high carbon chain ester.
  • Pentaerythritol tetraethylhexanoate was obtained as DUB PTO, a C37 ester commercially available from Alzo International Inc. of Sayerville, N.J. 7
  • Neopentyl glycol diheptanoate was obtained as LEXFEEL, a C7-C12 ester from Inolex Chemical Company of Philadelphia, Pa.
  • C12-C15 alkyl benzoate was obtained as FINSOLV TN, a C19-C22 ester from Innospec Inc. of Newark, Del.
  • Isononyl isonanoate was obtained as DUB ININ, a C18 ester commercially available from Stearinerie Dubois Inc. of Ciron, France.
  • Epidermal equivalents (EPI 200 HCF), multilayer and differentiated epidermis consisting of normal human epidermal keratinocytes, were purchased from MatTek (Ashland, Mass.). Upon receipt, epidermal equivalents were incubated for 24 hours at 37° C. in maintenance medium without hydrocortisone. Equivalents were topically treated (2 mg/cm 2 ) with formulation in example 1 for 2 hours before exposure to 100 ng/mL of Tumor Necrosis Factor- ⁇ (TNF ⁇ , available from Sigma-Aldrich of St Louis, Mo.). Equivalents were incubated for 4 hours at 37° C.
  • TNF ⁇ Tumor Necrosis Factor- ⁇
  • IL-8 Assays were performed as described in Example II. Compositions (described in Table 2) containing 4-hexyl resorcinol with different esters, each present at 3% by weight, were compared with Composition 6 according to the invention containing 3% by weight pentaerythritol tetraethylhexanoate. The results are shown in Table 4.
  • esters having high carbon chains (octyldodecyl neopentanoate and pentaerythritol tetraethylhexanoate, having 25 and 37 carbons, respectively) provide a substantial boost in the activity of 4-hexyl resorcinol over compositions without these esters.
  • Esters with lower carbon chains, neopentyl glycol diheptanoate, C12-C15 alkyl benzoate, and isononyl isonanoate provide only a modest boost or no boost at all to the activity of 4-hexyl resorcinol, even when used in relatively high concentrations.

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CA2827499A CA2827499C (en) 2012-09-24 2013-09-18 Low oil compositions comprising a 4-substituted resorcinol and a high carbon chain ester
AU2013231070A AU2013231070B2 (en) 2012-09-24 2013-09-19 Low oil compositions comprising a 4-substituted resorcinol and a high carbon chain ester
EP13185624.7A EP2712607B1 (en) 2012-09-24 2013-09-23 Low oil cosmetic compositions comprising a 4-substituted resorcinol and a high carbon chain ester
ES13185624T ES2732215T3 (es) 2012-09-24 2013-09-23 Composiciones cosméticas con un bajo contenido de aceite que contienen un resorcinol 4-sustituido y un éster con cadenas con un alto contenido de carbono
BR102013024429A BR102013024429B8 (pt) 2012-09-24 2013-09-24 Composições de óleo baixo compreendendo resorcinol 4-substituído e um éster de cadeia carbônica grande
KR1020130112977A KR102122181B1 (ko) 2012-09-24 2013-09-24 ４­치환된 레소르시놀 및 고 탄소 사슬 에스테르를 포함하는 저 오일 조성물
CN201310438957.XA CN103705402B (zh) 2012-09-24 2013-09-24 包含4‑取代的间苯二酚和高碳链酯的低油组合物
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CA2827499A1 (en) 2014-03-24
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ES2732215T3 (es) 2019-11-21
US10307352B2 (en) 2019-06-04
CN103705402B (zh) 2018-02-06
BR102013024429A2 (pt) 2014-10-21
AU2013231070A1 (en) 2014-04-10
BR102013024429B1 (pt) 2019-10-15
AU2013231070B2 (en) 2018-03-08
KR102122181B1 (ko) 2020-06-12
BR102013024429B8 (pt) 2022-08-30
US20160367452A1 (en) 2016-12-22
CA2827499C (en) 2020-11-03
KR20140040036A (ko) 2014-04-02

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