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WO2025096502A1 - Compositions longue tenue contenant un copolymère d'acrylate de silicone et une résine de silicone modifiée t - Google Patents

Compositions longue tenue contenant un copolymère d'acrylate de silicone et une résine de silicone modifiée t Download PDF

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Publication number
WO2025096502A1
WO2025096502A1 PCT/US2024/053507 US2024053507W WO2025096502A1 WO 2025096502 A1 WO2025096502 A1 WO 2025096502A1 US 2024053507 W US2024053507 W US 2024053507W WO 2025096502 A1 WO2025096502 A1 WO 2025096502A1
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WIPO (PCT)
Prior art keywords
composition
silicone resin
silicone
compositions
oil
Prior art date
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PCT/US2024/053507
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English (en)
Inventor
Jody EBANKS
Tsang-Min Huang
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LOreal SA
Original Assignee
LOreal SA
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Publication date
Priority claimed from US18/498,527 external-priority patent/US20250136813A1/en
Priority claimed from FR2400288A external-priority patent/FR3158231A3/fr
Application filed by LOreal SA filed Critical LOreal SA
Publication of WO2025096502A1 publication Critical patent/WO2025096502A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • 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
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • 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
    • A61K8/895—Polysiloxanes containing silicon bound to unsaturated aliphatic groups, e.g. vinyl dimethicone
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
    • A61Q1/06—Lipsticks
    • 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
    • A61K2800/31—Anhydrous

Definitions

  • OA23389-WO-PCT good application properties, good comfort properties and/or good appearance or stability properties (for example, consistency or uniformity in color over time).
  • lip compositions commercial products containing silicon resins such as MQ resins are known. Such products are known to provide good long wear properties and/or transfer-resistance. However, such products possess poor application properties and/or poor feel upon application (for example, feels rough). Therefore, a second composition (topcoat) is separately applied to such products to improve poor properties of the compositions to make the products acceptable to consumers.
  • U.S. Patent Application Nos.: 2020/0283628 and 2020/0283629 relate compositions containing MQ resin having certain silanol requirements.
  • U.S Patent 10,744,074 relates to compositions capable of forming a multilayer structure after application which can contain silicone acrylates as well as other silicone compounds.
  • U.S. Patent Application No.: 2021/0401723 relates to compositions capable of forming a multilayer structure after application which can contain T-modified MQ resin.
  • one aspect of the present invention is a care and/or makeup and/or treatment composition for keratinous materials which has good cosmetic properties such as, for example, good properties such as minimal or no flaking or cracking, good oil- and/or water-resistance, and/or good transfer-resistance properties after application.
  • the present invention relates to compositions comprising (1) at least one silicone acrylate copolymer and (2) at least one T-modified silicone resin.
  • such compositions further contain at least one MQ silicone resin and/or at least one glycerolated silicone resin.
  • such compositions are liquid.
  • the present invention also relates to anhydrous compositions comprising (1) at least one silicone acrylate copolymer and (2) at least one T-modified silicone resin.
  • such compositions further contain at least one MQ silicone resin and/or at least one glycerolated silicone resin.
  • such compositions are liquid.
  • the present invention also relates to colored compositions comprising (1) at least one coloring agent, (2) at least one silicone acrylate copolymer and (3) at least one T-modified silicone resin.
  • such compositions further contain at least one MQ silicone resin and/or at least one glycerolated silicone resin.
  • such compositions are liquid.
  • the present invention also relates to methods of treating, caring for and/or making up keratinous materials such as, for example, lips, skin or eyelashes, Atty. Docket No.: L1170432230WO (0425.1) OA23389-WO-PCT by applying compositions of the present invention to a keratinous material in an amount sufficient to treat, care for and/or make up the keratinous material.
  • the present invention also relates to methods of enhancing the appearance of keratinous materials such as, for example, lips, skin or eyelashes, by applying compositions of the present invention to a keratinous material in an amount sufficient to enhance the appearance of the keratinous material.
  • “Wax” as used herein is a lipophilic fatty compound that is solid at ambient temperature (25°C) and changes from the solid to the liquid state reversibly, having a melting temperature of more than 30°C and, for example, more than 45°C, and a hardness of more than 0.5 MPa at ambient temperature.
  • “Surfactant” and “emulsifier” are used interchangeably throughout this specification.
  • Polymer as used herein means a compound which is made up of at least two monomers.
  • Keratinous materials includes materials containing keratin such as hair, skin, eyebrows, lips and nails.
  • Substituted as used herein (unless otherwise indicated), means comprising at least one substituent.
  • Non-limiting examples of substituents include atoms, such as oxygen atoms and nitrogen atoms, as well as functional groups, such as hydroxyl groups, ether groups, alkoxy groups, acyloxyalky groups, oxyalkylene groups, polyoxyalkylene groups, carboxylic acid groups, amine groups, acylamino groups, amide groups, halogen containing groups, ester groups, thiol groups, sulphonate groups, thiosulphate groups, siloxane groups, hydroxyalkyl groups, and polysiloxane groups.
  • the substituent(s) may be further substituted.
  • “Volatile”, as used herein, means having a flash point of less than about 100 ⁇ C.
  • Non-volatile as used herein, means having a flash point of greater than about 100 ⁇ C. Atty. Docket No.: L1170432230WO (0425.1) OA23389-WO-PCT
  • “Anhydrous” means the compositions contain less than 1% water. Preferably, the compositions of the present invention contain less than 0.5% water, and preferably no water (free of water).
  • "Transfer” as used herein refers to the displacement of a fraction of a composition which has been applied to a keratinous material by contact with another substrate, whether of the same nature or of a different nature.
  • the composition when a composition such as a liquid lipstick has been applied, the composition can be transferred onto teeth or hands, or onto the cheek of another person. Irrespective of composition type, the composition can also transfer from the keratinous material to which it has been applied to another substrate such as napkins, collars, glasses, cups or other containers.
  • Transport-resistance refers to the quality exhibited by a composition in resisting transfer. To determine transfer-resistance, the amount of composition transferred from a keratinous material to a substrate may be evaluated and compared.
  • a composition may be transfer-resistant if, after application to a keratinous material such as lips, skin or eyelashes and contact with a substrate, a majority of the composition is left on the wearer. Further, the amount transferred may be compared with that transferred by other compositions, such as commercially-available compositions. In a preferred embodiment of the present invention, little or no composition is transferred to the substrate from the keratinous material.
  • "Long wear” compositions as used herein refers to compositions where the compositions, after application to a keratinous material, do not transfer or smudge after contact with another substrate and retain a consistent appearance on the keratinous material for an extended period of time. ”Long wear” compositions, as used Atty.
  • OA23389-WO-PCT herein can also refer to compositions where color remains the same or substantially the same as at the time of application, as viewed by the naked eye, after an extended period of time.
  • Long wear properties may be evaluated by any method known in the art for evaluating such properties. For example, long wear may be evaluated by a test involving the application of a composition to keratinous materials such as skin, eyelashes or lips and evaluating the color of the composition after an extended period of time. For example, the color of a composition may be evaluated immediately following application to the keratinous material and these characteristics may then be re-evaluated and compared after a certain amount of time.
  • composition of the present invention may be in any form, either liquid or non-liquid (semi-solid, soft solid, solid, etc.). For example, it may be a paste, a solid, a gel, or a cream.
  • composition of the invention may, for example, comprise an external or continuous fatty phase.
  • Free or “substantially free” or “devoid of” as it is used herein means that while it is preferred that no amount of the specific component be present in the composition, it is possible to have very small amounts of it in the compositions of the invention provided that these amounts do not materially affect at least one, preferably most, of the advantageous properties of the compositions of the invention.
  • free of animal-derived ingredients means that an effective amount (that is, Atty. Docket No.: L1170432230WO (0425.1) OA23389-WO-PCT more than trace amounts) of animal-derived ingredient(s) is/are omitted from the composition (that is, about 0% by weight), “substantially free of animal-derived ingredients” means that animal-derived ingredient(s) is/are present in amounts not greater than 0.1% by weight, and "devoid of animal-derived ingredients” means that animal-derived ingredient(s) is/are present in amounts not greater than 0.25% by weight, based on the total weight of the composition.
  • compositions of the present invention are preferably acidic, that is, less than 7, preferably 6.5 or less, preferably 6.0 or less, preferably 5.5 or less, including all ranges and subranges therebetween such as, for example 3 to 5, 4 to 6, 3 to 4.5, etc.
  • Compositions of the present invention may be in the form of a gel composition. Atty.
  • “Natural compound” refers to any compound derived directly from a natural substance such as a plant without having undergone any chemical modification.
  • “Compound of natural origin” refers to any compound derived from a natural compound which has undergone one or more chemical modifications, for example by organic synthesis reaction, without the properties of the natural compound having been modified.
  • “Synthetic compound” refers to any compound which is not a natural compound or a compound of natural origin.
  • Room temperature means 25°C.
  • “Atmospheric pressure” means 760 mmHg, i.e.10 5 pascals.
  • compositions and methods of the present invention can comprise, consist of, or consist essentially of the essential elements and limitations of the invention described herein, as well as any additional or optional ingredients, components, or limitations described herein or otherwise useful.
  • the film forming system or film forming component can consist essentially of (1) at least one silicone acrylate copolymer, (2) at least one T-modified silicone resin, and (3) optionally at least one MQ silicone resin and/or at least one glycerolated silicone resin.
  • the oil system or oil component can consist essentially of, or consist of, silicone oils, or volatile oils.
  • compositions, components and methods which “consist essentially of” identified ingredients or actions is “combined long wear and flexibility.”
  • Atty. Docket No.: L1170432230WO (0425.1) OA23389-WO-PCT [0045] Referred to herein are trade names for materials including, but not limited to polymers and optional components. The inventors herein do not intend to be limited by materials described and referenced by a certain trade name. Equivalent materials (e.g., those obtained from a different source under a different name or catalog (reference) number) to those referenced by trade name may be substituted and utilized in the methods described and claimed herein.
  • compositions including at least one silicone acrylate copolymer are provided. Silicone acrylate copolymers are polymers containing siloxane group(s) and hydrocarbon group(s).
  • suitable polymers include polymers comprising a hydrocarbon backbone such as, for example, a backbone chosen from vinyl polymers, methacrylic polymers, and/or acrylic polymers and at least one chain chosen from pendant siloxane groups, and polymers comprising a backbone of siloxane groups and at least one pendant hydrocarbon chain such as, for example, pendant vinyl, methacrylic and/or acrylic group(s).
  • Suitable silicone acrylate copolymers can comprise at least about 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, or 90% silicone (siloxane groups) by weight, and can Atty.
  • OA23389-WO-PCT comprise at least about 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, or 90% acrylate (hydrocarbon groups) by weight.
  • the at least one silicone acrylate copolymer can be chosen from silicone/(meth)acrylate copolymers, such as those as described in U.S. Patent Nos.: 5,061,481, 5,219,560, and 5,262,087, and U.S. Patent Application No.: 2012/0301415, the entire contents of all of which are hereby incorporated by reference.
  • the at least one silicone acrylate copolymer may be selected from polymers derived from non-polar silicone copolymers comprising repeating units of at least one polar (meth)acrylate unit and vinyl copolymers grafted with at least one non- polar silicone chain.
  • Non-limiting examples of non-dendrimer copolymers are acrylates/dimethicone copolymers such as those commercially available from Shin- Etsu, for example, the products sold under the tradenames KP-545 (cyclopentasiloxane (and) acrylates/dimethicone copolymer), KP-543 (butyl acetate (and) acrylates/dimethicone copolymer), KP-549 (methyl trimethicone (and) acrylates/dimethicone copolymer), KP-550 (INCI name: isododecane (and) acrylate/dimethicone copolymer), KP-561 (acrylates/stearyl acrylate/dimethicone acrylates copolymer), KP-562 (acrylates/behenyl acrylate/dimethicone acrylates copolymer), and mixtures thereof.
  • KP-545 cyclopentasiloxane (and)
  • Additional examples include the acrylate/dimethicone dendrimer copolymers sold by Dow Corning under the tradenames FA 4001 CM SILICONE ACRYLATE (cyclopentasiloxane (and) acrylates/polytrimethylsiloxymethacrylate copolymer) and FA 4002 ID SILICONE ACRYLATE (isododecane (and) acrylates/polytrimethylsiloxymethacrylate Copolymer), and mixtures thereof.
  • FA 4001 CM SILICONE ACRYLATE cyclopentasiloxane (and) acrylates/polytrimethylsiloxymethacrylate copolymer
  • FA 4002 ID SILICONE ACRYLATE isododecane (and) acrylates/polytrimethylsiloxymethacrylate Copolymer
  • These polymers may be sourced from various companies.
  • One such company is Minnesota Mining and Manufacturing Company which offers these types of polymers under the tradenames "Silicone Plus" polymers (for example, poly(isobutyl methacrylate-co-methyl FOSEA)-g-poly(dimethylsiloxane), sold under the tradename SA 70-5 IBMMF).
  • silicone acrylate copolymers include silicone/acrylate graft terpolymers, for example, the copolymers described in PCT Application No.: WO 01/32727, the disclosure of which is hereby incorporated by reference.
  • Other useful polymers can include those described in U.S. Patent No.: 5,468,477, the disclosure of which is hereby incorporated by reference.
  • a non- limiting example of these polymers is poly(dimethylsiloxane)-g-poly(isobutyl methacrylate), which is commercially available from 3M Company under the tradename VS 70 IBM.
  • the silicone acrylate copolymer preferably is present in the compositions of the present invention in an active solid content amount ranging from about 0.5% to about 25%, preferably from about 1% to about 20%, preferably from about 1.5% to about 15%, preferably from about 2% to about 10%, and preferably from about 2.5% to about 7.5%, by weight with respect to the total weight of the composition, including all ranges and subranges therebetween. It is to be understood that acceptable ranges of silicone acrylate copolymer present in invention Atty.
  • compositions comprising at least one T-modified silicone resin are provided.
  • T-modified silicone resin is understood to mean a silicone resin which comprises, in its chemical structure, one or more trifunctional units (T units) as well as one or more other units (M, D and/or Q) as described with respect to silicone resin nomenclature in this application.
  • the at least one T-modified silicone resin comprises at least two of these units, most preferably at least three of these units, with resins containing M, T and Q units being most preferred.
  • Silicone resin nomenclature is known in the art as “MDTQ” nomenclature, whereby a silicone resin is described according to the various monomeric siloxane units which make up the polymer. Each letter of “MDTQ” denotes a different type of unit. Tri-functional units (or T units) are part of this known nomenclature.
  • the at least one T-modified silicone resin is based on a siloxysilicate resin.
  • siloxysilicate resin is trimethylsiloxysilicate (MQ), which may be represented by the following formula: [0060] [(CH 3 )3SiO] x (SiO 4/2 ) y [0061] wherein x and y may, for example, range from 50 to 80.
  • MQ trimethylsiloxysilicate
  • Such non-T- modified siloxysilicates are commercially available from General Electric, Dow Corning, Wacker, Milliken, Siltech, Grant Industries, Momentive and Shin-Etsu Silicones under the tradename Resin MQ®. Atty.
  • the at least one T-modified silicone resin is a T-modified MQ resin in which at least one of the methyl groups of the M unit is replaced by a T unit.
  • Suitable T units for such replacements include, but are not limited to, polysilsesquioxanes of formula ((R)SiO3/2)x (T units) in which x is greater than 100, in which the R groups may independently be C1-C8 alkyl groups, such as substituted or unsubstituted C1-C8, branched or linear, lower alkyl groups such as, for example, methyl, ethyl, propyl, butyl, etc., with preferred groups being C1-C6 groups, preferably C1-C4 groups, preferably C1-C3 groups, and/or C3-C8 cyclic groups such as, for example, substituted or unsubstituted phenyl groups or C5- C6 groups cycloalkyl groups: polymethylsilsesquioxanes which are polysilsesquioxanes in which R is a methyl group; polypropylsilsesquioxanes in which R is a propyl group; and polyphen
  • the MQ resin is modified with one or more polymethylsilsesquioxanes.
  • T-modified MQ resin is GRANRESIN MQI-T50 from Grant Industries.
  • the at least one T-modified silicone resin is preferably present in an active solid content amount ranging from about 0.5% to about 25%, preferably from about 1% to about 20%, preferably from about 1.5% to about 15%, preferably from about 2% to about 10%, and preferably from about 2.5% to about 7.5%, by weight with respect to the total weight of the composition, including all ranges and subranges therebetween.
  • T-modified silicone resin present in invention compositions include 3%-6%, 2%-10%, 1-5%, 15%-25%, 15%-20%, 10%-20%, etc., by weight based on the weight of the composition. Atty.
  • the weight ratio of active material of (1) silicone acrylate copolymer to (2) T-modified silicone resin is from about 7:1 to about 1:7, from about 5:1 to about 1:5, from about 3:1 to about 1:3, and from about 2:1 to about 1:2 including any ratio ranges therein such as about 1:1 and/or which can be discerned by using the amounts of ingredients in the examples of this application as and endpoint of a range.
  • more silicone acrylate copolymer is present in the compositions of the present invention than T-modified silicone resin.
  • compositions optionally further comprising at least one MQ silicone resin and/or at least one glycerolated silicone resin are provided.
  • compositions of the present invention comprise a film forming component comprising, consisting of, or consisting essentially of at least one silicone acrylate copolymer, at least one T-modified silicone resin, and at least one MQ silicone resin and/or at least one glycerolated silicone resin.
  • Such resins are distinct from t-modified silicone resins which contain T units as discussed above and from glycerolated silicone resins which contain monoglycerol or polyglycerol group(s) as discussed below.
  • Atty. Docket No.: L1170432230WO (0425.1) OA23389-WO-PCT [0068]
  • the term “glycerolated silicone resin” is understood to mean a resin which comprises, in its chemical structure, one or more monoglycerol or polyglycerol group(s).
  • alkyl siloxysilicates of formula [(R1)3SiO1/2]x(SiO4/2)y (units MQ) in which x and y are integers from 20 to 200, preferably from 40 to 150, and preferably from 50 to 80, including all ranges and subranges therebetween, and such that the group R1 represents an alkyl group containing from 1 to 8 carbon atoms or a hydroxyl group, preferably a methyl group.
  • Suitable MQ silicone resins include MQ resins such as trimethylsiloxysilicates represented by the following formula: [0071] [(CH3)3SiO]x(SiO4/2)y [0072] wherein x and y may, for example, range from 20 to 200, preferably from 40 to 150, and preferably from 50 to 80, including all ranges and subranges therebetween. [0073] As examples of silicone resins of MQ type of trimethyl siloxysilicate type, mention may be made of those sold under the reference SR1000 by the company Momentive Performance Materials, under the reference MQ 1600 by Dow Corning or under the reference Belsil TMS 803 by the company Wacker.
  • silicone resins of comprising MQ siloxysilicate units mention may also be made of phenylalkyl siloxysilicate resins, such as phenylpropyldimethyl siloxysilicate (Silshine 151 sold by the company Momentive Performance Materials). The preparation of such resins is described especially in patent US 5817302, the entire contents of which is hereby incorporated by reference. Atty.
  • the glycerolated silicone resin(s) can be preferably chosen from those of following formula (1): [0076] in which [0077] - each R 1 , which are identical or different, is an alkyl, aryl or aralkyl group of 1 to 30 carbon atoms, or a group substituted by a halogen, a group substituted by an amino or a group substituted by a carboxyl of the latter; [0078] - each R 2 is a mono- or polyglycerol group of following general formula (2): [0079] in which [0080] - R 4 is a substituted or unsubstituted monovalent hydrocarbon group or a hydrogen atom, and [0081] - the indices l and i are numbers which satisfy the conditions 0 ⁇ l ⁇ 15 and 0 ⁇ i ⁇ 5, [0082] - each R 3 is
  • each R 1 which are identical or different, is an alkyl, aryl or aralkyl group of 1 to 30 carbon atoms, or a group substituted by a halogen, a group substituted by an amino or a group substituted by a carboxyl of the latter; [0085] - the indices m, j and k1 to k3 are numbers which satisfy the conditions [0086] - the indices a, b, c, d, e and f are numbers which satisfy the conditions 0 ⁇ a ⁇ 400, 0 ⁇ b ⁇ 200, 0 ⁇ c ⁇ 400, 0 ⁇ d ⁇ 320, 0 ⁇ e ⁇ 320, 0 ⁇ f ⁇ 1000 and 0.5 ⁇ (a + b + c)/f ⁇ 1.5.
  • the glycerolated silicone resin(s) of formula (1) as defined above are chosen from those for which [0089] - the indices b and c satisfy the conditions 0 ⁇ b ⁇ 30 and 0 ⁇ c ⁇ 30; [0090] - the index i in the general formula (2) of the monoglycerol or polyglycerol group R 2 is a number which satisfies the condition 0 ⁇ i ⁇ 3.
  • the glycerolated silicone resin(s) of formula (1) are in the solid form at 25°C when the index c satisfies the condition 0 ⁇ c ⁇ 400 and R 3 is a group of general formula (3) where the index j satisfies the condition 0 ⁇ j ⁇ 10.
  • the glycerolated silicone resin(s) exhibit a weight-average molecular weight ranging from 1000 to 100000.
  • the glycerolated silicone resin(s) according to the invention are amphiphilic, that is to say exhibit two parts of different polarities. In general, one is lipophilic (soluble or dispersible in an oily phase).
  • the other is hydrophilic (soluble or dispersible in water). They are characterized by the value of their HLB (Hydrophilic- Atty. Docket No.: L1170432230WO (0425.1) OA23389-WO-PCT Lipophilic Balance), the HLB being the ratio of the hydrophilic part to the lipophilic part in the molecule.
  • HLB Hydrophilic- Atty. Docket No.: L1170432230WO (0425.1) OA23389-WO-PCT Lipophilic Balance
  • the term HLB is well known to a person skilled in the art and is described, for example, in “The HLB System. A Time-Saving Guide to Emulsifier Selection” published by ICI Americas Inc., 1984).
  • the value of the HLB of the glycerolated silicone resins according to the invention preferably varies from 0.1 to 15 according to the Griffin method.
  • the glycerolated silicone resin(s) according to the invention can be obtained by a preparation process comprising the stage of hydrosilylation [0095] A) of a silicone resin containing a hydrosilyl group of formula (7) below [0096] in which: [0097] - each R 1 , which are identical or different, is an alkyl, aryl or aralkyl group of 1 to 30 carbon atoms, or a group substituted by a halogen, a group substituted by an amino or a group substituted by a carboxyl of the latter; [0098] - the indices a, b, c, d, e and f are numbers which satisfy the conditions 0 ⁇ a ⁇ 400, 0 ⁇ b ⁇ 200, 0 ⁇ c ⁇ 400, 0 ⁇ d ⁇ 320, 0 ⁇ e ⁇ 320, 0 ⁇ f ⁇ 1000 and 0.5 ⁇ (a + b + c
  • R 4 is a substituted or unsubstituted monovalent hydrocarbon group or a hydrogen atom
  • indices l and i are numbers which satisfy the conditions 0 ⁇ l ⁇ 15 and 0 ⁇ i ⁇ 5
  • indices m, j and k1 to k3 are numbers which satisfy the conditions 0 ⁇ m ⁇ 5, 0 ⁇ j ⁇ 500, 0 ⁇ k 1 ⁇ 2, 0 ⁇ k 2 ⁇ 2 and 0 ⁇ k 3 ⁇ 2; said silicone resin containing a hydrosilyl group of formula (7) which reacts with at least one compound in the formula (8).
  • the hydrosilylation reaction is carried out in the presence, for example, of a platinum or rhodium catalyst.
  • a platinum or rhodium catalyst The preferred ranges for b, c, d, e, f, R 4 , l, m, i, j and k 1 to k 3 are as defined above.
  • Process for the preparation of the glycerolated silicone resin [00108] A specific example of process for the preparation of the glycerolated silicone resin according to the invention is described below. [00109] As mentioned above, the glycerolated silicone resin according to the invention can be obtained by the stage of hydrosilylation [00110] (A) of a silicone resin containing a hydrosilyl group of mean formula (7) below: Atty.
  • each R 1 is an identical or different alkyl, aryl or aralkyl group of 1 to 30 carbon atoms, or a group substituted by a halogen, a group substituted by an amino or a group substituted by a carboxyl of the latter;
  • the indices a, b, c, d, e and f are numbers which satisfy the conditions 0 ⁇ a ⁇ 400, 0 ⁇ b ⁇ 200, 0 ⁇ c ⁇ 400, 0 ⁇ d ⁇ 320, 0 ⁇ e ⁇ 320, 0 ⁇ f ⁇ 1000 and 0.5 ⁇ (a + b + c)/f ⁇ 1.5;
  • - n is a number which satisfies the condition 1 ⁇ n ⁇ 3, with [00115] (B
  • the organosilicon resin containing hydrosilyl groups of mean composition formula (7) and the compound having terminal alkenyl groups of general formula (8), (9), (10), (11) or (12) are mixed in a molar ratio, expressed as hydrosilyl groups/terminal unsaturated groups, which is preferably from 0.5 to 2.0 and more preferentially from 0.8 to 1.2.
  • the addition reaction is preferably carried out in the presence of a platinum or rhodium catalyst. Specific examples include chloroplatinic acid, chloroplatinic acid modified by an alcohol and chloroplatinic acid/vinylsiloxane complexes.
  • the amount of platinum or of rhodium is preferably 50 ppm or less and more preferably 20 ppm or less.
  • the addition reaction can be carried out in the presence of an organic solvent.
  • cyclic organopolysiloxanes such as octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane and dodecamethylcyclohexasiloxane
  • aromatic hydrocarbons such as toluene and xylene
  • solvents of ketone type such as acetone, methyl ethyl ketone, diethyl ketone and methyl isobutyl ketone
  • aliphatic hydrocarbons such as hexane, heptane, octane and cyclohexane
  • aliphatic alcohols such as methanol, ethanol, 1-propanel, 2- propanol, 1-butanol, 2-methyl-1-propanol, 2-butanol, 2-methyl-2-propanol, 1-pentanol, 2-methylbutanol, 2-pentanol, 1-hexano
  • the amount of solvent used is preferably from 1% to 80% and more preferably from 5% to 50% of the overall reaction system. In the above range, the reaction system is kept uniform and the reaction takes place efficiently.
  • the conditions of the addition reaction are not particularly limited, although heating at reflux at a temperature of between 50 and 150°C, in particular between 80 and 120°C, for approximately 1 to 10 hours is preferred.
  • the stage of removal of the rhodium or platinum catalyst used with activated carbon can be included.
  • the amount of activated carbon used is preferably from 0.001% to 5.0% and in particular from 0.01% to 1.0% of the overall system.
  • the discoloration of the sample can be better suppressed by fixing the amount of activated carbon in this range.
  • the stage of removal of the remaining hydrosilyl groups can be included. In particular in the cases where use in applications such as cosmetic preparations is anticipated, there exists a possibility of these hydrosilyl groups becoming deactivated over time due to dehydrogenation reactions, which presents a problem from the viewpoint of safety. It is thus preferable to include a stage of maintenance of the hydrosilyl groups.
  • stage of removal of the hydrosilyl groups is the process of hydrolysis of the unreacted hydrosilyl groups by the addition of a basic catalyst, such as an alkali metal carbonate, an alkali metal bicarbonate or an alkali metal hydroxide, and then neutralization by the addition of an amount of acid catalyst equal to the molar equivalent of the basic catalyst.
  • a basic catalyst such as an alkali metal carbonate, an alkali metal bicarbonate or an alkali metal hydroxide
  • an amount of acid catalyst equal to the molar equivalent of the basic catalyst.
  • Specific examples of the basic catalyst comprise strong basic catalysts, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide and barium hydroxide; and weak basic catalysts, such as sodium carbonate, calcium carbonate and sodium bicarbonate. Atty.
  • a strong basic catalyst is particularly preferred, sodium hydroxide being particularly preferred.
  • acid catalysts of hydrochloric acid, sulfuric acid, sulfurous acid, fuming sulfuric acid, oxalic acid, p-toluenesulfonic acid, methanesulfonic acid, trifluoroacetic acid, trifluoromethanesulfonic acid, phosphoric acid, formic acid, acetic acid, propionic acid, benzoic acid and citric acid.
  • Typical examples of the stage of deodorization comprise two approaches. The first is that in which, by adding an acid catalyst to the solution after the addition reaction, any propenyl ether remaining in the system is hydrolyzed and the propionaldehyde which is formed is removed by strip purification (JP No.2137062).
  • Specific examples of the acid catalyst used in the first approach comprise hydrochloric acid, sulfuric acid, sulfurous acid, fuming sulfuric acid, oxalic acid, p-toluenesulfonic acid, methanesulfonic acid, trifluoroacetic acid, trifluoromethanesulfonic acid, phosphoric acid, formic acid, acetic acid, propionic acid, benzoic acid and citric acid.
  • These acids are used in combination with water.
  • an acid having a low boiling point such as hydrochloric acid, formic acid, acetic acid or trifluoroacetic acid.
  • a strong acid such as hydrochloric acid or trifluoroacetic acid.
  • the treatment temperature is preferably fixed at 80°C or less in order to prevent the oxidation of the hydrophilic groups.
  • the amount of acidic aqueous solution added is preferably fixed from 0.1% to 100%, with respect to the organosilicon resin modified by organic groups. The use of 5% to 30% is more preferred.
  • the process consisting of adding an aqueous solution to the post reaction solution so as to regulate the pH at 7 or less and of carrying out a strip purification after stirring under heating is preferred. Atty.
  • the purification of the strip can be carried out at normal temperature or under reduced pressure.
  • the temperature conditions are preferably fixed at 120°C or less. In order to efficiently purify the strip under these temperature conditions, it is preferable to carry out this operation under reduced pressure; when it is carried out at normal pressure, the operation is preferably carried out under a stream of inert gas, such as nitrogen or argon.
  • the second approach is that in which, by adding hydrogen to the solution after the addition reaction, the unsaturated double bonds are alkylated (subjected to a hydrogenation reaction) and the formation of propionaldehyde over time is controlled in a stable manner (U.S.
  • the hydrogenation reactions comprise methods involving the use of hydrogen and methods involving the use of metal hydrides, and there also exist homogeneous reactions and heterogeneous reactions. These methods can be used alone but it is also possible to use in them combination. However, given the advantage that there is no trace of catalyst used in the product, a heterogeneous catalytic hydrogenation reaction using a solid catalyst is preferred.
  • the solid catalyst is, for example, nickel, palladium, platinum, rhodium, cobalt, chromium, copper, iron and others, in the uncombined form or in the compound form. In this case, it is not necessary to use a catalyst support.
  • the support can, for example, be activated carbon, silica, silica/aluminum, aluminum or zeolite.
  • These catalysts can be used alone but it is also possible to use them in combination.
  • the preferred catalyst is Raney nickel, which is economically advantageous. As the Raney nickel is generally developed and used with an alkali, it is necessary to carefully measure the pH of the reaction system. Furthermore, the reaction system becomes weakly alkaline, which is particularly Atty. Docket No.: L1170432230WO (0425.1) OA23389-WO-PCT effective for the deodorization when the hydrolysis reaction is carried out with an acidic aqueous solution.
  • the hydrogenation reaction it is preferable to carry out the hydrogenation reaction at a pressure generally of between 1 and 100 MPa and between 50 and 200°C.
  • the hydrogenation reaction can be carried out batchwise or continuously. When it is a noncontinuous process, the reaction time depends, for example, on the amount of catalyst and on the temperature but it is generally of between 3 and 12 hours.
  • the hydrogen pressure can be adjusted to an appropriate fixed pressure.
  • the final point of the hydrogenation reaction is the point at which the hydrogen pressure has ceased to change and it can thus be determined by carefully monitoring a manometer.
  • the amount of aldehyde included in the glycerolated silicone resin which has been purified by this acid treatment and this hydrogenation treatment can be fixed at 70 ppm or less, preferably at 20 ppm or less and more preferably at 10 ppm or less.
  • the weight-average molecular weight of the glycerolated silicone resin of mean formula (1) preferably varies from 1000 to 100000; from the viewpoint of the performance qualities and of the ease of the operations, such as the filtration, the weight-average molecular weight preferentially varies from 3000 to 50000.
  • the weight-average molecular weight can be determined as the polystyrene-equivalent weight-average molecular weight in gel permeation chromatography (GPC).
  • GPC gel permeation chromatography
  • the glycerolated silicone resin according to the invention of formula (1) for which the indices b and c satisfy the conditions 0 ⁇ b ⁇ 30 and 0 ⁇ c ⁇ 30, the index i in the general formula (2) is a number which satisfies the condition 0 ⁇ i ⁇ 3 and the index j in the general formula (3) satisfies the condition 0 ⁇ j ⁇ 10 is the form of a solid at 25°C and preferably exhibits a weight-average molecular weight which preferably varies from 1000 to 100000 and more preferentially from 3000 to 50000.
  • the glycerolated silicone resins according to the invention have a hydrophilic-lipophilic balance (HLB), as determined by the Griffin formula, preferably of 0.1 to 15 and more preferably of 1.0 to 8.0.
  • HLB hydrophilic-lipophilic balance
  • the composition of the invention comprises at least one glycerolated silicone resin in the formula (1) of the (3- Atty.
  • the glycerolated silicone resin of the (3-Glyceroxypropyl) Dimethylsiloxyl Trimethylsiloxysilicate type of formula (21) is in the form of a solution in at least one volatile oil.
  • the volatile oil can be chosen from the group constituted of hydrocarbon oils, silicone oils and their mixtures.
  • hydrocarbon oil is understood to mean an oil containing predominantly hydrogen and carbon atoms and optionally one or more functions chosen from hydroxyl, ester, ether and carboxyl functions.
  • the term “silicone oil” denotes an oil comprising at least one Si-O group and more particularly an organopolysiloxane.
  • the volatile hydrocarbon oils can be chosen from branched C8-C16 alkanes. Mention may in particular be made, as C8-C16 isoalkanes of petroleum origin (also known as isoparaffins), such as isododecane (also known as 2,2,4,4,6-pentamethylheptane), isodecane, isohexadecane and, for example, the oils sold under the Isopar ⁇ or Permethyl ⁇ tradenames. More preferentially, isododecane will be used.
  • the volatile silicone oil can be chosen from volatile silicone oils, such as volatile linear or cyclic silicone oils, in particular those having a viscosity of 2 to 8 centistokes (2.10 -6 to 8.10 -6 m 2 /s) and containing in particular from 2 to 7 silicon atoms, these silicones optionally comprising alkyl or alkoxy groups containing from 1 to 10 carbon atoms.
  • volatile silicone oils such as volatile linear or cyclic silicone oils, in particular those having a viscosity of 2 to 8 centistokes (2.10 -6 to 8.10 -6 m 2 /s) and containing in particular from 2 to 7 silicon atoms, these silicones optionally comprising alkyl or alkoxy groups containing from 1 to 10 carbon atoms.
  • volatile silicone oils which can be used in the invention, of octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyl- trisiloxane, heptamethyloctyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane and dodecamethylpentasiloxane; and their mixtures. More preferentially, decamethylcyclopentasiloxane (D5) will be used.
  • the glycerolated silicone resin of the (3-Glyceroxypropyl) Dimethylsiloxy Trimethylsiloxysilicate type of formula (21) is in the form of the solution comprising 49.5% by weight of active material in isododecane, such as the product manufactured under the tradename X-25- 9138A ⁇ by SHIN ETSU with a weight-average molecular weight of 11000.
  • the MQ silicone resin(s) and/or glycerolated silicone resin(s) is (are) preferably present in a content as active material ranging from about 0.1% to about 30% by weight, with respect to the total weight of the composition, preferably ranging from about 0.2% to about 20% by weight, preferably from about 0.5% to about 15% by weight, and preferably from about 1% to about 10% by weight with respect to the total weight of the composition, including all ranges and subranges therebetween such as 1% to 5%, 5% to 25%, 1% to 7.5%, 2% to 12.5%, etc.
  • compositions of the present invention further comprising at least one fatty substance are provided. Suitable fatty substances include oil(s) and/or wax(es). “Oil” means any non-aqueous medium which is liquid at ambient temperature (25 ⁇ C) and atmospheric pressure (760 mm Hg).
  • a "wax” for the purposes of the present disclosure is a lipophilic fatty compound that is solid at ambient temperature (25°C) and changes from the solid to the liquid state reversibly, having a melting temperature of more than 30°C and, for example, more than 45°C, which can be as high as 150°C, a hardness of more than 0.5 MPa at ambient temperature, and an anisotropic crystalline organization in the solid state.
  • Suitable oils include volatile and/or non-volatile oils.
  • compositions of the present invention preferably comprise one or more volatile silicone oils such as those discussed above.
  • volatile silicone oils include linear or cyclic silicone oils having a viscosity at room temperature less than or equal to 6 cSt and having from 2 to 7 silicon atoms, these silicones being optionally substituted with alkyl or alkoxy groups of 1 to 10 carbon atoms.
  • Other volatile oils which may be used include KF 96A of 6 cSt viscosity, a commercial product from Shin Etsu having a flash point of 94°C.
  • the volatile silicone oils have a flash point of at least 40°C.
  • a volatile linear silicone oil may be employed in the present invention.
  • Suitable volatile linear silicone oils include those described in U.S. Patent No.: 6,338,839 and WO 03/042221, the contents of which are incorporated herein by reference.
  • the volatile linear silicone oil is decamethyltetrasiloxane.
  • the decamethyltetrasiloxane is further combined with another solvent that is more volatile than decamethyltetrasiloxane.
  • the composition of preferably comprises one or more non-silicone volatile oils and may be selected from volatile hydrocarbon oils, volatile esters and volatile ethers such as those discussed above.
  • volatile non-silicone oils include, but are not limited to, volatile hydrocarbon oils having from 8 to 16 carbon atoms and their mixtures and in particular branched C8 to C16 alkanes such as C8 to C16 isoalkanes (also known as isoparaffins), isohexacecane, isododecane, isodecane, and for example, the oils sold under the trade names of Isopar or Permethyl.
  • the volatile non-silicone oils have a flash point of at least 40°C.
  • volatile non-silicone volatile oils are given in Table 2 below.
  • Table 2 Compound Flash Point (°C) I d d 43 Atty. Docket No.: L1170432230WO (0425.1) OA23389-WO-PCT
  • the volatility of the solvents/oils can be determined using the evaporation speed as set forth in U.S. patent no.6,338,839, the contents of which are incorporated by reference herein.
  • the composition comprises at least one non-volatile oil.
  • non-volatile oils examples include, but are not limited to, polar oils such as: [00167] - hydrocarbon-based plant oils with a high triglyceride content consisting of fatty acid esters of glycerol, the fatty acids of which may have varied chain lengths, these chains possibly being linear or branched, and saturated or unsaturated; these oils are especially wheat germ oil, corn oil, sunflower oil, karite butter, castor oil, sweet almond oil, macadamia oil, apricot oil, soybean oil, rapeseed oil, cottonseed oil, alfalfa oil, poppy oil, pumpkin oil, sesame seed oil, marrow oil, avocado oil, hazelnut oil, grape seed oil, blackcurrant seed oil, evening primrose oil, millet oil, barley oil, quinoa oil, olive oil, rye oil, safflower oil, candlenut oil, passion flower oil or musk rose oil; or caprylic/capric acid trig
  • polar oils such as:
  • L1170432230WO (0425.1) OA23389-WO-PCT ricinoleates of alcohols or of polyalcohols; hydroxylated esters, for instance isostearyl lactate or diisostearyl malate; and pentaerythritol esters; [00169] - synthetic ethers containing from 10 to 40 carbon atoms; [00170] - C8 to C26 fatty alcohols, for instance oleyl alcohol, cetyl alcohol, stearyl alcohol, and cetearyl alcohol; and [00171] - mixtures thereof.
  • non-volatile oils examples include, but are not limited to, non-polar oils such as branched and unbranched hydrocarbons and hydrocarbon waxes including polyolefins, in particular Vaseline (petrolatum), paraffin oil, squalane, squalene, hydrogenated polyisobutene, hydrogenated polydecene, polybutene, mineral oil, pentahydrosqualene, and mixtures thereof.
  • non-polar oils such as branched and unbranched hydrocarbons and hydrocarbon waxes including polyolefins, in particular Vaseline (petrolatum), paraffin oil, squalane, squalene, hydrogenated polyisobutene, hydrogenated polydecene, polybutene, mineral oil, pentahydrosqualene, and mixtures thereof.
  • non-volatile oils examples include, but are not limited to, silicone oils such as dimethicone (polydimethylsiloxane) of various viscosities as well as phenylated silicone oils such as phenyl trimethicone and trimethylsiloxyphenyl dimethicone.
  • the at least one oil is present in the compositions of the present invention in an amount ranging from about 10 to about 80% by weight, more preferably from about 20 to about 70% by weight, and most preferably from about 25 to about 60% by weight, based on the total weight of the composition, including all ranges and subranges within these ranges, such as 30-65%, 40-60%, 30-55%, etc.
  • the compositions of the present invention further comprise at least one wax. Suitable examples of waxes that can be used in accordance with the present disclosure include Atty.
  • OA23389-WO-PCT those generally used in the cosmetics field: they include those of natural origin, such as beeswax, carnauba wax, candelilla wax, ouricoury wax, Japan wax, cork fibre wax or sugar cane wax, rice bran wax, rice wax, montan wax, paraffin wax, lignite wax or microcrystalline wax, ceresin or ozokerite, and hydrogenated oils such as hydrogenated castor oil or jojoba oil; synthetic waxes such as the polyethylene waxes obtained from the polymerization or copolymerization of ethylene, and Fischer- Tropsch waxes, or else esters of fatty acids, such as octacosanyl stearate, glycerides which are solid at 30°C, for example at 45°C.
  • natural origin such as beeswax, carnauba wax, candelilla wax, ouricoury wax, Japan wax, cork fibre wax or sugar cane wax, rice bran wax, rice wax, montan wax
  • compositions of the present invention further include at least one silicone wax.
  • suitable silicone waxes include, but are not limited to, silicone waxes such as alkyl- or alkoxydimethicones having an alkyl or alkoxy chain ranging from 10 to 45 carbon atoms, poly(di)methylsiloxane esters which are solid at 30°C.
  • alkylated silicone acrylate copolymer waxes comprising at least 40 mole % of siloxy units having the formula (R 2 R'SiO 1/2 ) x (R''SiO 3/2 ) y , where x and y have a value of 0.05 to 0.95, R is an alkyl group having from 1 to 8 carbon atoms, an aryl group, a carbinol group, or an amino group, R is a monovalent hydrocarbon having 9-40 carbon atoms, R'' is a monovalent hydrocarbon group having 1 to 8 carbon atoms, an aryl group such as those disclosed in U.S.
  • compositions of the present invention contain less than 1% wax.
  • compositions of the present invention contain less than 0.5% wax.
  • the compositions of the present invention contain no wax.
  • compositions of the present invention may optionally further comprise at least one coloring agent.
  • the coloring agent(s) is/are preferably chosen from pigments, dyes, nacreous pigments, pearling agents, and mixtures thereof.
  • Representative liposoluble dyes which may be used according to the present invention include Sudan Red, DC Red 17, DC Green 6, ß-carotene, soybean oil, Sudan Brown, DC Yellow 11, DC Violet 2, DC Orange 5, annatto, and quinoline yellow.
  • the liposoluble dyes when present, generally have a concentration ranging up to 40% by weight of the total weight of the composition, such as from 0.0001% to 30%, including all ranges and subranges therebetween.
  • the nacreous pigments which may be used according to the present invention may be chosen from colored nacreous pigments such as titanium mica with iron oxides, titanium mica with ferric blue or chromium oxide, titanium mica Atty.
  • OA23389-WO-PCT with an organic pigment chosen from those mentioned above, and nacreous pigments based on bismuth oxychloride.
  • the nacreous pigments if present, be present in the composition in a concentration ranging up to 50% by weight of the total weight of the composition, such as from 0.0001% to 40%, preferably from 0.001% to 30%, including all ranges and subranges therebetween.
  • the pigments which may be used according to the present invention, may be chosen from white, colored, inorganic, organic, polymeric, and nonpolymeric pigments.
  • mineral pigments include titanium dioxide, zirconium oxide, zinc oxide, cerium oxide, iron oxides, chromium oxides, manganese violet, ultramarine blue, chromium hydrate, and ferric blue.
  • organic pigments include carbon black, pigments of D & C type, and lakes based on cochineal carmine, barium, strontium, calcium, and aluminum.
  • the coloring agents may be present in the composition in a concentration ranging up to 50 % by weight of the total weight of the composition, such as from 0.0001% to 40%, and further such as from 0.001% to 30%, including all ranges and subranges therebetween.
  • compositions of the present invention may also optionally contain water.
  • water When the compositions of the present invention contain water, they are preferably in the form of an emulsion.
  • the compositions of the present invention when they contain water, they are in the form of an oil-in-water emulsion (O/W) or a water-in-oil emulsion (W/O).
  • O/W oil-in-water emulsion
  • W/O water-in-oil emulsion
  • the oil phase contains predominantly silicone oils (Si/W or W/Si emulsion) or hydrocarbon oils.
  • water is preferably present in an amount of from about 10% to Atty.
  • compositions of the present invention are devoid of water, substantially free of water, or free of water as defined herein.
  • the compositions of the present invention are anhydrous.
  • the composition of the invention can also comprise any additive usually used in the field under consideration.
  • additional film formers other than the at least one silicone acrylate and the at least one T-modified or glycerolated silicone resin, dispersants such as poly(12-hydroxystearic acid), antioxidants, essential oils, sunscreens, preserving agents, fragrances, fillers, neutralizing agents, cosmetic and dermatological active agents such as, for example, emollients, moisturizers, vitamins, essential fatty acids, surfactants, silicone elastomers, thickening agents, gelling agents, particles, pasty compounds, viscosity increasing agents can be added.
  • emollients such as, for example, emollients, moisturizers, vitamins, essential fatty acids, surfactants, silicone elastomers, thickening agents, gelling agents, particles, pasty compounds, viscosity increasing agents
  • emollients such as, moisturizers, vitamins, essential fatty acids, surfactants, silicone elastomers, thickening agents, gelling agents, particles, pasty compounds, viscosity increasing
  • compositions of the invention should be cosmetically or dermatologically acceptable, i.e., it should contain a non-toxic physiologically acceptable medium and should be able to be applied to the keratinous materials of human beings such as, for example, lips, skin or eyelashes.
  • suitable gelling agents for the oil phase include, but are not limited to, lipophilic or hydrophilic clays.
  • hydrophilic clay means a clay that is capable of swelling in water; this clay swells in water and forms after hydration a colloidal dispersion.
  • These clays are products that are already well known per se, which are described, for example, in the book “Mineralogie des argiles", S. Caillere, S. Henin, M. Rautureau, 2nd edition 1982, Masson, the teaching of which is included herein by way of reference.
  • Clays are silicates containing a cation that may be chosen from calcium, magnesium, aluminium, sodium, potassium and lithium cations, and mixtures thereof.
  • clays of the smectite family such as montmorillonites, hectorites, bentonites, beidellites and saponites, and also Atty. Docket No.: L1170432230WO (0425.1) OA23389-WO-PCT of the family of vermiculites, stevensite and chlorites. These clays may be of natural or synthetic origin.
  • Hydrophilic clays that may be mentioned include synthetic hectorites (also known as laponites), for instance the products sold by the company Laporte under the names Laponite XLG, Laponite RD and Laponite RDS (these products are sodium magnesium silicates and in particular sodium lithium magnesium silicates); bentonites, for instance the product sold under the name Bentone HC by the company Rheox; magnesium aluminium silicates, especially hydrated, for instance the products sold by the Vanderbilt Company under the names Veegum Ultra, Veegum HS and Veegum DGT, or calcium silicates, and especially the product in synthetic form sold by the company under the name Micro-cel C.
  • synthetic hectorites also known as laponites
  • Laponite XLG, Laponite RD and Laponite RDS these products are sodium magnesium silicates and in particular sodium lithium magnesium silicates
  • bentonites for instance the product sold under the name Bentone HC by the company Rheox
  • magnesium aluminium silicates especially hydrated
  • lipophilic clay means a clay that is capable of swelling in a lipophilic medium; this clay swells in the medium and thus forms a colloidal dispersion.
  • modified clays such as modified magnesium silicate (Bentone Gel VS38 from Rheox), and hectorites modified with a C 10 to C 22 fatty-acid ammonium chloride, for instance hectorite modified with distearyldimethylammonium chloride (CTFA name: disteardimonium hectorite) sold under the name Bentone 38 CE by the company Rheox or Bentone 38V® by the company Elementis.
  • silica particles are fumed silica particles.
  • Suitable silicas include, but are not limited to, hydrophobic silicas, such as pyrogenic silica optionally with hydrophobic surface treatment whose particle size is less than 1 micron, preferably less than 500 nm, preferably less than Atty. Docket No.: L1170432230WO (0425.1) OA23389-WO-PCT 100 nm, preferably from 5 nm to 30 nm, including all ranges and subranges therebetween .
  • silica it is in fact possible to modify the surface of silica chemically, by a chemical reaction producing a decrease in the number of silanol groups present on the surface of the silica.
  • the silanol groups can notably be replaced with hydrophobic groups: a hydrophobic silica is then obtained.
  • the hydrophobic groups can be: [00201] trimethylsiloxyl groups, which are notably obtained by treatment of pyrogenic silica in the presence of hexamethyldisilazane. Silicas treated in this way are called "Silica silylate" according to the CTFA (6th edition, 1995).
  • the gelling agent if present, is present in the composition of the present invention in amounts of active material generally ranging from about 0.1% to about 10%, preferably from about 0.25% to about 5%, and more preferably from about 0.5% to about 3.5%, by weight, based on the total weight of the composition, including all ranges and subranges in between.
  • compositions of the present invention by applying compositions of the present invention to the keratinous material in an amount sufficient Atty. Docket No.: L1170432230WO (0425.1) OA23389-WO-PCT to treat, care for and/or make up the keratinous material are provided.
  • “making up” the keratinous material includes applying at least one coloring agent to the keratinous material in an amount sufficient to provide color to the keratinous material.
  • compositions of the present invention are applied topically to the desired area of the keratinous material in an amount sufficient to treat, care for and/or make up the keratinous material, to cover or hide defects associated with keratinous material, or to enhance the appearance of keratinous material.
  • the compositions may be applied to the desired area as needed, preferably once daily, and then preferably allowed to dry before subjecting to contact such as with clothing or other objects.
  • the composition is allowed to dry for about 4 minutes or less, more preferably for about 2 minutes or less.
  • Particularly preferred embodiments include: [00208] A composition comprising (1) at least one silicone acrylate copolymer and (2) at least one T-modified silicone resin; [00209] The composition of the preceding embodiment, wherein the composition further comprises at least one MQ silicone resin; [00210] The composition of any preceding embodiment, wherein the composition further comprises at least one glycerolated silicone resin; Atty.
  • composition of any preceding embodiment wherein the composition is anhydrous; [00212] The composition of any preceding embodiment, wherein the composition is liquid; [00213] The composition of any preceding embodiment, wherein the composition further comprises at least one coloring agent; [00214] The composition of any preceding embodiment, further the composition further comprises at least one volatile oil; [00215] The composition of any preceding embodiment, wherein the silicone acrylate copolymer is an acrylates/dimethicone copolymer; and [00216] A method of making up lips comprising applying the composition of any preceding embodiment to lips in an amount sufficient to makeup the lips.
  • Example 1 – Sample Invention Compositions [00220] The following compositions can be prepared: Ingredient General Range (active Specific Range (active content) content) [00221]
  • Example 2 – Testing Procedures [00222]
  • Example 2B Stretch Test Procedure
  • Each Sample 1-5 (below) was drawn down on 3x1 window on a 4x2 section of nitrile glove with a 1/2'' border on all sides created using tape, and each sample was allowed to dry overnight and the tape was removed. Then, each sample was stretch 10 times a total of 6 inches to determine the impact on flexibility, using the following grading scale: Rating Scale Atty.
  • Example 3 Testing [00230] Three types of compositions were prepared having high (15- 20%), medium (8-19.9%) or low (1-7.9%) active film former (silicone acrylate copolymer and/or silicone resin(s)(T-modified, MQ, and/or glycerolated) as follows: Sample Sample Sample Sample Sample 1 2 3 4 5 1 00 100 100 100 100 00 [00231 ted for extended wear and flexibility according to the procedures in Example 2, where the droplets were allowed to sit for 10 minutes. The results of this testing are set forth below: N ame Oil Oil KW Saliva Saliva KW Acetic Acid A.A.
  • Example 4 The base composition of Sample 5 was used to prepare compositions containing differing ratios of silicone acrylate copolymer and various silicone resins. The total final solid content of silicone acrylate copolymer and silicone resins was 20% in each composition.
  • the compositions thus prepared can be summarized: Sample Title Ratio of Polymers Sample A Silicone acrylate copolymer (KP) 100% l B M ili R i M 1 [00235] The actual formulations were as follows:
  • Sample H [00237] Sample A had good flexibility as indicated by a 0 in the stretch test, however, its long wear properties (e.g., olive oil test) were impacted. [00238] Samples B, C, and D, each containing a single silicone resin, had poor flexibility. [00239] Sample E had good flexibility as indicated by a 1 in the stretch test, however, its long wear properties (e.g., olive oil test) were slightly impacted. [00240] Samples H and I possessed inferior flexibility.
  • Samples F and J without MQ silicone resin showed both excellent long wear and flexibility properties.
  • Samples G and K with MQ silicone resin showed both excellent long wear and flexibility properties, with Sample K having better long wear properties (e.g., olive oil test).

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Abstract

L'invention concerne des compositions comprenant au moins un copolymère d'acrylate de silicone et au moins une résine de silicone modifiée T, ainsi que des procédés d'application de telles compositions sur des matières kératiniques.
PCT/US2024/053507 2023-10-31 2024-10-30 Compositions longue tenue contenant un copolymère d'acrylate de silicone et une résine de silicone modifiée t Pending WO2025096502A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US18/498,527 US20250136813A1 (en) 2023-10-31 2023-10-31 Long-wear compositions containing silicone acrylate copolymer and t-modified silicone resin
US18/498,527 2023-10-31
FRFR2400288 2024-01-12
FR2400288A FR3158231A3 (fr) 2024-01-12 2024-01-12 Compositions longue tenue contenant un copolymère d’acrylate de silicone et une résine de silicone t-modifiée

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WO2025096502A1 true WO2025096502A1 (fr) 2025-05-08

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FR3104990A1 (fr) * 2019-12-23 2021-06-25 L'oreal Gel émulsionné pour les lèvres
KR20210097959A (ko) * 2020-01-31 2021-08-10 (주)아모레퍼시픽 유중수형 화장료 조성물
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