WO2010126919A1 - Compositions and methods incorporating photocatalysts - Google Patents

Compositions and methods incorporating photocatalysts Download PDF

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Publication number
WO2010126919A1
WO2010126919A1 PCT/US2010/032640 US2010032640W WO2010126919A1 WO 2010126919 A1 WO2010126919 A1 WO 2010126919A1 US 2010032640 W US2010032640 W US 2010032640W WO 2010126919 A1 WO2010126919 A1 WO 2010126919A1
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WO
WIPO (PCT)
Prior art keywords
substrate
active material
photocatalyst
composition
light
Prior art date
Application number
PCT/US2010/032640
Other languages
English (en)
French (fr)
Inventor
Alan David Willey
Ellen Schmidt Baker
William Richard Mueller
Ioannis Constantine Constantinides
Original Assignee
The Procter & Gamble Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US12/433,958 external-priority patent/US20090285768A1/en
Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to MX2011011253A priority Critical patent/MX2011011253A/es
Priority to JP2012508612A priority patent/JP2012525479A/ja
Priority to CN201080019558.4A priority patent/CN102428151B/zh
Priority to CA2759043A priority patent/CA2759043C/en
Priority to EP10719685A priority patent/EP2424947A1/en
Priority to BRPI1015355A priority patent/BRPI1015355A2/pt
Priority to RU2011142246/04A priority patent/RU2537838C2/ru
Publication of WO2010126919A1 publication Critical patent/WO2010126919A1/en

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89Polysiloxanes
    • A61K8/891Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/893Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by an alkoxy or aryloxy group, e.g. behenoxy dimethicone or stearoxy dimethicone
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/12Preparations containing hair conditioners
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D167/00Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D167/04Polyesters derived from hydroxycarboxylic acids, e.g. lactones
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04Polysiloxanes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04Polysiloxanes
    • C09D183/06Polysiloxanes containing silicon bound to oxygen-containing groups
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04Polysiloxanes
    • C09D183/08Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M23/00Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M23/00Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
    • D06M23/005Applying monomolecular films on textile products like fibres, threads or fabrics
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M23/00Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
    • D06M23/06Processes in which the treating agent is dispersed in a gas, e.g. aerosols
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/81Preparation or application process involves irradiation
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/0008Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/0008Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0033Additives activating the degradation of the macromolecular compound

Definitions

  • a composition for and method of covalent modification of surface properties of a substrate comprising a silicone polymer, copolymer and mixtures thereof and an active material having functional groups capable of covalent attachment to a substrate in the presence of an acid or a base, a photocatalyst capable of generating an acid or a base upon exposure to light, and a vehicle.
  • Materials may be characterized in terms of bulk properties and surface properties.
  • the overall properties of a material are controlled in significant part by the surface properties and the bulk properties of the material.
  • the surface properties of a material are largely controlled by the surface chemistry and surface structure of the material.
  • the bulk properties of a material are largely controlled by the bulk chemistry and bulk structure of the material. It is sometimes desirable to modify the surface chemistry and/or surface structure of a material in order to produce certain surface properties. In addition, it is sometimes desirable to modify the bulk chemistry and/or bulk structure of a material in order to produce certain bulk properties.
  • Substrates including hair and skin are of interest in terms of surface and/or bulk modification. Substrates are repeatedly exposed to mechanical washings, chemical treatments and environmental conditions which are among the many factors that may result in the loss of the substrates desirable properties such as natural and synthetically created shine, luster and texture. Moreover, environmental factors may add to these effects and substantially contribute to weathered or damaged substrates. Acute damage to the surface of substrates including hair and skin may build over time, resulting in chronic damage.
  • compositions and methods to compensate for things such as F-layer and stratum corneum loss from hair fibers and skin, respectively, that provides a durable conditioning and protective benefit Covalent modification of the surface properties of damaged substrates materials is one example of such an approach.
  • Modification of the surface of a material by locally forming an active material on the material surface by reacting one or more active components to create covalent bonds between the one or more active components and modification the bulk of a material by forming active material in a similar manner within the bulk of the material are promising approaches.
  • a composition comprising: an active material having one or more functional groups capable of covalent attachment in the presence of an acid or a base to one or more complementary functional groups; a photocatalyst capable of generating an acid or a base upon exposure to light; and a vehicle for dispersing or dissolving the active material and photocatalyst for application of the composition to a substrate; wherein the active material is selected from the group consisting of silicone polymers, copolymers, and mixtures thereof and at least one organic functional group.
  • a method for treating a substrate comprising applying to the substrate the composition previously described and exposing the composition-treated substrate to ambient light.
  • this method can be carried out in multiple steps wherein the method comprises the steps of applying at least one active material to the substrate, the active material having one or more functional groups, and the substrate having one or more complementary functional groups; applying to the substrate at least one photocatalyst capable of generating an acid or base on exposure to light; and exposing the photocatalyst and the at least one active material to light.
  • exposure to light results in the forming covalent attachments between the one or more functional groups of the at least one active material and the substrate.
  • FIG. 1 is a schematic diagram that illustrates damage to the FCSM of a fiber comprising a covalently bound to 18-MEA by way of thioester bonds.
  • FIG. 2 is a schematic diagram that illustrates one non-limiting embodiment of the compositions and methods described herein for treating substrates including fibers with an active component and a photocatalyst.
  • FIG. 3 and 3A are schematic diagrams that illustrate one non-limiting embodiment of the compositions and methods described herein for treating physiological substrates such as fibers with an active component and a photocatalyst.
  • FIG. 4 is a schematic representation of one non-limiting embodiment of a mechanism of action of the compositions and methods described herein where a substrate surface is covalently modified.
  • FIG. 5 is a schematic representation of non- limiting embodiment of a mechanism of action of the compositions and methods described herein where a substrate surface is covalently modified.
  • FIG. 6 is a schematic representation of non- limiting embodiment of a mechanism of action of the compositions and methods described herein where a porous substrate material is treated with an active material capable of forming a secondary active material.
  • the term "functional group” means an atom or group of associated atoms that, at least in part, defines the structure and determines the properties of a particular family of chemical compounds.
  • a functional group may be a region on or in a molecule or material that is a site of specific chemical reactivity compared to other regions of the molecule or material.
  • Functional groups generally have characteristic properties and may control, in part, the reactivity of a molecule as a whole.
  • Functional groups include, but are not limited to, hydroxyl groups, thiol groups, carbonyl groups, carboxyl groups, sulfonate groups, sulfide groups, ether groups, halogen atoms, amino groups, cyano groups, nitro groups, and the like.
  • Compounds that are generally classified (structurally and/or functionally) according to functional groups include, but are not limited to, alkanes, alkenes, alkynes, aromatic compounds, halides, alcohols, ethers, esters, amines, imines, imides, carboxylic acids, amides, acid halides, acid anhydrides, nitriles, ketones, aldehydes, carbonates, peroxides, hydroperoxides, carbohydrates, acetals, epoxides, sulfonic acids, sulfonate esters, sulfides, sulfoxides, thioethers, thiocyanates, disulfides, phosphonic acids, phosphate esters, phosphines, azides, azo compounds, nitro compounds, nitrates, nitriles, nitrites, nitroso compounds, thiols, cyanates, and isocyanates, for example.
  • active material means substances to be applied to a substrate to modify the surface and/or bulk properties of the substrate material. These terms may be used interchangeably.
  • Substrate surface properties may include, for example, surface hydrophobicity/hydrophilicity, oleophobicity/oleophilicity, color, optical properties, absorptivity, adsorptivity, bonding capability, brightness, dullness, frictional resistance, stain resistance, surface texture, odor, washability, wettability, elasticity, plasticity, and rigidity.
  • Substrate bulk properties may include, for example, tensile strength, rigidity, absorptivity, elasticity, plasticity, and biological activity.
  • Active materials may include compounds having one or more functional groups capable of covalent attachment in the presence of an acid or a base to one or more complementary functional groups present at the surface or in the bulk of a substrate. Active materials may also include compounds capable of forming covalent bonds between molecules in the presence of an acid or a base, for example, monomers capable of acid or base catalyzed polymerization and, or copolymerization.
  • a "cosmetically active material” is an active material suitable for use in a personal care product without undue toxicity, incompatibility, instability, allergic response, and the like.
  • polymer as used herein means a compound that may be covalently bonded to other monomers (that may have the same or different chemical structures) to form a polymer and, or copolymer.
  • polymer and copolymer as used herein means a compound comprising a plurality of monomers. Accordingly, as used herein the term polymer and, or copolymer includes dimers, trimers, oligomers, and the like.
  • the terms “modify”, “modification”, “functionalize” or “functionalization”, with regard to a substrate refers to (1) covalently attaching an active component to the substrate surface, (2) covalently attaching an active component to the substrate in the bulk of the substrate material, (3) forming covalent bonds between two or more active components (which may be the same or different chemical moieties) where the resultant secondary active material localizes to the substrate surface, and/or (4) forming covalent bonds between two or more active components (which may be the same or different chemical moieties) where the actives components are present within the bulk of the substrate.
  • consumer care product means a product such as, for example, soft surface cleaners, hard surface cleaners, glass cleaners, ceramic tile cleaners, toilet bowl cleaners, wood cleaners, multi-surface cleaners, surface disinfectants, dishwashing compositions, laundry detergents, fabric conditioners, fabric dyes, surface protectants, surface disinfectants, motor vehicle surface treatments, and other like consumer products.
  • Consumer care products includes form such as liquids, gels, suspensions, powders, and the like. Consumer care products may also be for household or home care use as well as for professional, commercial and/or industrial use.
  • Consumer care products include "personal care product” such as, for example, lipsticks, mascaras, rouge, foundations, blush, eyeliners, lip liners, lip gloss, nail polish, nail conditioner other cosmetics; personal care products including facial powders, body powders; hair treatment products including mousse, hair spray, styling gels, shampoo, hair conditioner (leave-in or rinse- out), cream rinse, hair dye, hair coloring product, hair shine product, hair serum, hair anti-frizz product, hair split-end repair product, permanent waving solution, antidandruff formulation; bath gels, shower gels, body washes, facial cleaners, skin care products including sunscreen and sun block lotions, lip balm, skin conditioners, cold creams, moisturizers, body spray, soap, body scrub, exfoliants, astringent, scrubbing lotion, depilatory, antiperspirant composition, deodorant, shaving product, pre-shaving product, after shaving product, toothpaste, mouthwash, or oral care strips.
  • personal care products including facial powders, body powders
  • cleaning includes compositions for cleaning substrates including, but not limited to hair or skin, including scalp, face, and body. Accordingly, the term “shampoo” includes, but is not limited to, the conventional understanding of a hair shampoo, a body wash, a face wash, or other surface washing composition, for example. In addition, the term “shampoo” includes compositions for use on humans and/or animals.
  • conditioner means a composition for treating substrates comprising fibrous material including fabrics, hair, and skin that includes scalp, face, and body, in order to provide protection to the substrate from mechanical, chemical, and/or environmental factors that contribute to damage and, or weathering, and/or to alleviate the characteristics of such damage.
  • conditioner includes, but is not limited to, the conventional understanding of a fabric and hair conditioner (leave-on and/or rinse-out), a skin lotion, or a facial moisturizer, for example.
  • One object of the compositions and methods described herein is to provide for the modification of the surface and/or bulk properties of a substrate by covalently attaching an active material to the surface of the substrate.
  • Another object of the compositions and methods described herein to provide for the modification of the surface and/or bulk properties of a substrate by treating the substrate with active compounds capable of reacting with each other to form covalent bonds between two or more molecules of the active compounds thereby forming a secondary active material.
  • the various embodiments relate, in general, to compositions and methods for treating a substrate.
  • substrate means any material for which it is useful to treat the surface and/or bulk of that material with the compositions and methods described herein.
  • substrate and material may be used interchangeably in the context of substances to be modified by the compositions and methods described herein.
  • physiological materials including, but not limited to, physiological materials such as, for example, hair, skin, nails, gums, and teeth.
  • Substrate may also mean non-physiological materials such as, for example, fabric, paper, wood, plastic, glass, tile, stone, concrete, brick, other ceramics, coated or painted metal surfaces, coated glass, polymeric films, and composites or combinations thereof.
  • Substrates may also include surfaces that have been previously modified such as, for example, coated surfaces (e.g., varnished or painted) or laminated surfaces.
  • coated surfaces e.g., varnished or painted
  • laminated surfaces e.g., laminated surfaces.
  • the terms "substrate” and "material” may be used interchangeably in the context of substances to be modified by the compositions and methods described herein.
  • the compositions described herein include an active component that can modify a substrate in the presence of an acid or a base, a photocatalyst capable of generating an acid or a base upon exposure to light, and a suitable vehicle, which may optionally be a physiological acceptable vehicle.
  • compositions described herein may also include one or more optional components, including surfactants, emulsifiers, oxidants, reductants, pH regulators, emollients, humectants, proteins, peptides, amino acids, additive polymer or copolymers, glossers, essential oils and/or fatty acids, lubricants, sequestrants/chelators, antistatic agents, rheology modifiers, feel agents, fillers, preservatives, perfumes, other functional components, or combinations thereof.
  • optional components including surfactants, emulsifiers, oxidants, reductants, pH regulators, emollients, humectants, proteins, peptides, amino acids, additive polymer or copolymers, glossers, essential oils and/or fatty acids, lubricants, sequestrants/chelators, antistatic agents, rheology modifiers, feel agents, fillers, preservatives, perfumes, other functional components, or combinations thereof.
  • the methods described herein include treating a substrate by forming one or more covalent bonds between an active material and/or the substrate, where the covalent bond is formed in the presence of an acid or base generated by a photocatalyst upon exposure to light.
  • the methods described herein include treating a substrate by forming one or more covalent bonds between two or more active component's molecules, where the covalent bond is formed in the presence of an acid or base generated by a photocatalyst upon exposure to light and the active material localizes to the surface and/or bulk of the substrate.
  • the term "molecule" means a sufficiently stable group of at least two atoms in a definite arrangement held together by chemical bonds.
  • the term molecule includes, but is not limited to, neutral molecular compounds, polyatomic ions, radical species, biomolecules, monomers, dimers, trimers, oligomers, polymer or copolymers, and the like.
  • the methods described herein include treating a substrate by preparing and covalently bonding a active material to the substrate, or forming covalent bonds between active materials on the substrate surface or in the substrate bulk, in situ, by providing a substrate, providing one or more reagents, providing a photocatalyst, and exposing the photocatalyst to light in the presence of the substrate and the one or more reagents, where the photocatalyst generates an acid or a base, the acid or the base catalyzes reaction between the one or more reagents and/or reaction between the one or more reagents and the substrate, and where the reaction(s) forms covalent bonds.
  • the methods described herein include providing a system including a substrate, an active material that can modify a substrate in the presence of an acid or a base, and a photocatalyst capable of generating an acid or a base upon exposure to light, and exposing the system to light.
  • a system including a substrate, an active material that can modify a substrate in the presence of an acid or a base, and a photocatalyst capable of generating an acid or a base upon exposure to light, and exposing the system to light.
  • covalent attachment of active materials on substrates such as hair and skin, for example, often proves difficult to achieve. This is especially true in the presence of water, which may rapidly degrade reactive moieties before substrate functionalization occurs.
  • aqueous media are known to chemically facilitate hydrolysis and oxidation reactions that may compete against covalent attachment of active materials to substrates. This may pose particular problems, for example, in consumer care products where water is often used as a physiologically acceptable vehicle.
  • substrates such as, for example, hair, skin, fabric, glass and ceramic may not contain particularly reactive chemical functional groups on the surface that would readily react with active components to form covalent bonds.
  • This relatively low substrate surface reactivity may result in a reaction system that is outside the practical time frame of an apply-and-rinse environment (e.g., shampooing and conditioning hair, washing skin, laundering fabrics, or cleaning hard surfaces).
  • strict regulatory requirements concerning product safety and environmental protection increase the challenge of providing compositions and methods for treating a substrate such as, for example, hair, skin, fabric, glass or ceramic, through covalent attachment of active components.
  • the various embodiments of the compositions and methods described herein are directed toward a photocatalyst technology that allows the use of light to promote a reaction such as, for example, the covalent attachment of an active component to a substrate or formation of covalent bonds between two or more active components in situ on the surface or in the bulk of a substrate material.
  • the various embodiments may be used, for example, to promote the covalent attachment of long-chain alkyl groups to damaged hydrophilic hair and/or skin in order to replenish and/or fortify the normally hydrophobic character of these substrates.
  • the various embodiments may be used, for example, to promote the covalent attachment of active materials to fabrics or hard surfaces.
  • the various embodiments may be used, for example, to locally polymer or copolymerize monomers on the surface and/or in the bulk of substrate materials in order to modify the surface and/or bulk properties of a material.
  • covalent attachment may yield a variety of substantial benefits.
  • fibers such as hair or fabric may experience conditioning benefits including, among others, improved feel, lower friction, ease of manipulation such as weaving, braiding combing/brushing, reduced dryness, increased smoothness, decreased frizziness, increased shine, decreased levels of static, and improved protection against damage due to other mechanical, chemical and environmental factors.
  • conditioning benefits including, among others, improved feel, lower friction, ease of manipulation such as weaving, braiding combing/brushing, reduced dryness, increased smoothness, decreased frizziness, increased shine, decreased levels of static, and improved protection against damage due to other mechanical, chemical and environmental factors.
  • physiological substrates such as skin conditioning benefits may include, among others, decreased dryness, decreased redness, decreased itchiness, decreased flaking, and improved texture and smoothness. At least some of these benefits may be imparted by increased or targeted deposition of actives resulting from the surface modification via covalent attachment.
  • benefits may include reduced water spotting, increased shine or luster and easier subsequent cleaning.
  • the benefits imparted by the compositions and methods described herein are potentially more durable because a non-labile covalent bond is employed, which is generally stronger and more stable relative to the absorption, adsorption, hydrogen bonding, ionic bonding, other electrostatic interactions, and/or other transient non-covalent associations employed in prior conditioners to deposit or apply active components onto hair and/or skin. This may substantially reduce the frequency of application and reapplication encountered with prior conditioners.
  • compositions and methods described herein provide for the covalent attachment of active materials to substrates, which may be described as an approach toward repairing and/or fortifying the hair F-layer or skin stratum corneum for example.
  • the F-layer of virgin hair may be stripped from the hair fiber by processes mediated by various mechanical, chemical, and/or environmental factors as illustrated in FIG. 1. These processes may include, for example, the oxidative and hydrolytic reactions commonly encountered during permanent hair coloring and permanent waving processes.
  • FIG. 1 is a schematic diagram that illustrates the FCSM of a hair fiber comprising a keratinous epicuticle portion covalently bound to 18-MEA by way of thioester bonds between the carboxyl group on the 18-MEA and the thiol group on cysteine residues in the keratin protein in the epicuticle.
  • Hydrolytic and/or oxidative processes may remove at least a portion of the F-layer by cleaving the cysteine-lipid thioester bond, leaving exposed epicuticle comprising sulfonate groups on the cysteine residues.
  • the anionic sulfonate groups on the cysteine residues at the surface of the epicuticle render the surface of any damaged hair fibers hydrophilic, which may result in the undesirable properties of damaged hair.
  • the more hydrophilic (and consequently the more damaged) the hair fibers the lower the deposition of prior hydrophobic conditioning actives (such as, for example, dimethylsiloxanes, fatty alcohols and acids, and quaternary amines) by non-covalent interactions and associations. Accordingly, the compositions and methods described herein provide an attractive approach for treating such damaged substrates.
  • FIG. 2 schematically illustrates one non-limiting embodiment of the compositions and methods described herein for treating substrates.
  • a composition comprising an active component having a hydroxyl group (R-OH) and a photocatalyst capable of generating an acid or a base upon exposure to light is provided in the presence of a substrate comprising surface sulfonate and carboxyl groups.
  • the photocatalyst is exposed to light, which causes the photocatalyst to form an acid or a base.
  • the acid or base catalyzes the formation of a covalent ester bond between the hydroxyl group on the active material and the carboxyl group on the substrate.
  • FIG. 3 and FIG. 3A viewed together, schematically illustrate one non-limiting embodiment of the compositions and methods described herein for treating substrates.
  • a portion of a hair fiber comprising a lipid layer (F-layer) and a protein layer (epicuticle) is shown.
  • the protein layer comprises structural proteins such as, for example, keratin having disulfide bonds between cysteine residues.
  • the hair may be treated with a reducing agent to break the disulfide bonds and form respective thiol groups.
  • the hair may be further treated with an active component comprising one or more compounds capable of reaction to form covalent bonds between the one or more active component compounds and/or between the one or more active component compounds and the thiol groups.
  • the hair fiber is also treated with a photocatalyst.
  • the one or more active components and the photocatalyst penetrate the surface of the hair fiber substrate.
  • the hair fiber substrate treated with the one or more active components and photocatalyst is exposed to light of suitable wavelength to activate the photocatalyst and catalyze reaction between the one or more active components within the hair fiber substrate and the thiol groups.
  • the active materials may be one or more monomers capable of polymerizing or copolymerizing in the presence of acid or base.
  • Fibers are treated with a composition comprising photocatalyst and active material monomers that at least partially penetrate the fiber.
  • the photocatalyst Upon exposure to light, the photocatalyst is activated thereby generating acid or base, which catalyzes the active material monomers to polymerize or copolymerize the monomers, thereby forming a active material polymer or copolymer in situ, which may optionally attach to the fiber by way of covalent bonds formed between the thiol groups and the polymer or copolymer.
  • these active material polymers or copolymers do not covalently attach to the fiber.
  • the polymer or copolymer formed in situ may be physically immobilized on the surface of the hair fiber or within pores in the hair fiber.
  • the polymer or copolymer formed in situ may also be associated with the hair fiber by a physical and/or chemical interaction such as, for example, adsorption, absorption, electrostatic interaction, frictional interaction, steric interaction, and/or size exclusion effects with the surface and/or bulk of the substrate.
  • the active material monomers may be styrene or a styrene derivative such as, for example, ⁇ - methyl styrene.
  • the monomer may also comprise mixtures of different monomers such that the in situ polymer or copolymerization (on the surface and/or in the bulk of the substrate) produces copolymer or copolymer.
  • FIG. 4 schematically illustrates one non-limiting embodiment of the compositions and methods described herein for treating substrates.
  • a composition comprising an active material having a carboxyl group and a photocatalyst capable of generating an acid or a base upon exposure to light is provided in the presence of a substrate comprising surface hydroxyl groups.
  • the photocatalyst is exposed to light, which causes the photocatalyst to form an acid or a base.
  • the acid or base catalyzes the formation of a covalent ester bond between the hydroxyl group on the substrate and the carboxyl group on the active material.
  • FIG. 5 is a schematic representation of one non-limiting embodiment of a mechanism of use of the compositions and methods described herein in the context of a photoacid catalyst.
  • a reagent solution is provided that includes a reagent, which may be an active component, and a photoacid catalyst.
  • the reagent solution may comprise a shampoo, a conditioner, other personal care product or a consumer care product.
  • the reagent solution is applied to a substrate, which may be skin, hair, fabric, or a hard surface, for example.
  • the components of the reagent solution deposit on the surface of the substrate.
  • the system comprising the reagent solution and the substrate is exposed to light. The light causes the deprotonation of the photocatalyst.
  • a photoacid-catalyzed esterification reaction occurs between the reagent and the substrate surface.
  • un- reacted catalyst, reagent, and protons diffuse from the substrate surface and are removed from the system.
  • the modified/functionalized substrate is dried.
  • the modified/functionalized substrate is washed and rinsed. The modified/functionalized substrate substantially retains the covalently bound reagent after washing and rinsing.
  • FIG. 6 is a schematic representation of one non-limiting embodiment of the compositions and methods described herein.
  • a porous substrate material 10 is provided.
  • the substrate material 10 includes a substrate surface 15 and a bulk portion 20 having pores 25.
  • the substrate material 10 is treated with a composition comprising an active material 30 and a photocatalyst 35.
  • the active material 30 may comprise molecules capable of reacting together in the presence of an acid or a base to form a secondary compound.
  • the active material 30 may comprise one or more types of monomer capable of reacting to form polymer or copolymer in the presence of acid or base.
  • the active material 30 and the photocatalyst 35 penetrate, at least in part, the surface 15 of the substrate 10 into the bulk portion 20 through pores 25.
  • the substrate 10 is exposed to light of suitable wavelength to activate the photocatalyst 35, which generates acid or base to catalyze the reaction of the active material 30 on the surface 15 and/or in the bulk portion 20.
  • a secondary active material forms from two or more active components of the composition catalyzed in situ.
  • This secondary active material 40 attaches to the surface 15 and/or in the bulk portion 20 of substrate material 10.
  • Secondary active material 40 may comprise polymers, copolymers or combinations thereof, for example.
  • the secondary active material 40 may form a polymer network 45 that may modify the surface and/or bulk properties of the substrate material 10.
  • the secondary active material formed according to the photocatalyzed acid or base mechanism described herein may localize to the surface and/or bulk of the substrate material.
  • the localization may be a result of covalent attachment of the secondary active material to the substrate material.
  • the localization may be a result of non- covalent chemical or physical interactions between the secondary active material and the surface and/or bulk of the substrate material.
  • FIG. 6 illustrates a secondary active material comprising a polymer network that is immobilized on the surface and partially in the bulk of a substrate material due to the physical formation of the polymer within pores located in the material.
  • FIG. 6 illustrates a secondary active material comprising a polymer network that is immobilized on the surface and partially in the bulk of a substrate material due to the physical formation of the polymer within pores located in the material.
  • the secondary active material formed according to the photocatalyzed acid or base mechanism described herein may localize on the surface of a substrate and/or in the bulk of the substrate due to interactions such as adsorption, absorption, electrostatic interaction, frictional interaction steric interaction, and/or size exclusion effects. This allows for the manipulation of various material properties such as, for example, porosity of the treated substrate.
  • the active material and, or the secondary active material formed according to the photocatalyzed acid or base mechanism described herein may localize on the surface of a substrate and/or in the bulk of the substrate due to changes in the properties of the these material when covalent bonds form between their molecules.
  • the active material comprises a monomer/polymer system
  • the active material may be polymerized and/or crosslinked on the surface of a substrate. The polymerization and/or crosslinking may change the solubility of the active material in the reaction medium, which may facilitate the deposition of the secondary active material onto the substrate surface. In this manner, a surface layer of secondary active material may form on the substrate surface thereby modifying the surface properties.
  • the photocatalyzation acid or base transforms the active material so it covalently bonds to the substrate (surface and/or bulk) as described herein.
  • compositions and methods described herein facilitate in situ and localized modification of material properties in a controlled manner.
  • the active components are covalently altered (e.g., by the formation of covalent bonds between them to form a secondary active material and/or between active components and a substrate material) in a photoacid or photobase reaction system.
  • the substrate to be modified may be treated by spraying, soaking, spreading, coating, rinsing, or any other suitable means of introducing the composition onto the surface of the substrate or into the bulk of the substrate material.
  • the active material is at least partially insoluble in the vehicle, it is important to maximize contact between the active material and the substrate by, for example, minimizing the drop size or particle size of the active in the vehicle.
  • the covalent modification only occurs on those areas of the substrate surface (and underlying bulk) that are both in contact with a reagent solution and irradiated with light of a wavelength suitable to activate the photocatalyst. This allows for control of the location and extent of the surface and/or bulk modification.
  • the acid or base photocatalytic covalent modification/functionalization mechanisms described herein may also be reversible.
  • substrate surfaces covalently modified or functionalized through esterification and/or thioesterification reactions may be contacted with an acidic aqueous surfactant solution.
  • an alkaline surfactant solution may be employed. These solutions may facilitate the hydrolytic cleavage of the ester and/or thioester bonds attaching the active components to the substrate, thereby removing the active components. This removability is limited to active component- substrate bonds that are reversible under the appropriate conditions.
  • the ester bond is formed when the reagent and the catalyst are present in the vicinity of the substrate and exposed to the appropriate light.
  • the high concentration of protons at the moment of irradiation results in ester bond formation that remains intact because the generated protons diffuse rapidly into the bulk of the medium.
  • the low content of the photoacid allows for subsequent stable and near-neutral pH of the bulk aqueous solution. Under these conditions the ester bond is hydrolyzed at a very slow rate.
  • treatment with significantly lower (or significantly higher) pH aqueous solutions will more readily break the ester bonds resulting in the original unmodified substrate surface.
  • the removal of the covalently-attached active can also be achieved by treatment of the modified or functionalized substrate with a composition including a photocatalyst (photoacid or photobase).
  • a composition including a photocatalyst photoacid or photobase.
  • This allows for improved control over the timing of the removal of the active component from the substrate.
  • This can be achieved if the photocatalyst is chosen so that it is unaffected by ambient light but can generate acid or base species under light of a specific wavelength provided by an appropriate device.
  • the active material of the present invention comprises branched, cyclic, crosslinked and combinations of thereof silicone polymer, copolymer and combinations of polymers and copolymer having molecular weights of at least 150 grams/mole, alternatively 1000 grams/mole, from 3000 grams/mole to 10 million grams/mole, 10,000 grams/mole to 7 million grams /mole, or 50,000 grams/mole to 4 million grams/mole; and at least one organic functional group (and in one embodiment multiple groups), including but not limited to hydroxyl, amino, carboxyl sulphonate, thiol, epoxide, ester groups and/or any combination thereof, and iii) the level and nature of substitution and molecular weight of the silicone polymer or copolymer can be appropriately selected, depending on the desired substrate modification and application conditions.
  • silicone copolymer or copolymer can be from monomers which contain organic alcohol groups (primary and secondary) including those having the structure: Rl - [Si(CH2)(R3-CH2OH)-O]n- [Si(CH2)2-O]m - R2
  • hair modification can be achieved by treating damaged hair with a silicone polymer and, or copolymer active material.
  • Treatment with such an active material in emulsion, dispersion, and/or solutions with a photoacid generator, such as 8-hydroxyquinoline can provide damaged hair with benefits that are durable, for example, that are persistent after multiple shampoo wash cycles.
  • durable benefits include hair softness (wet and dry), compatibility, anti-frizz, style and color retention, moisturization, and shine.
  • the surface modification method involves formation of covalent bonds between silicone polymer or copolymer and the substrate.
  • the bonds are created by acid-catalyzed reaction of the primary or secondary alcohol of the polymer or copolymer with compatible functional groups of the hair substrate (for example carboxylic acid groups toward condensation).
  • Suitable silicone polymer and copolymers include those having an alkoxyalkanol group.
  • the silicone polymer and, or copolymer is a Bis-Hydroxyethoxypropyl Dimethicone having the structure:
  • Suitable Bis-Hydroxyethoxypropyl Dimethicones include, but are not limited to, those materials available as 5562 Carbinol Fluid from Dow Corning, and Baysilone OF OH 702 E from Momentive.
  • the photocatalyst may be any acid, base (or conjugate thereof) having a pKa (or pKb) value that decreases (or increases) upon exposure to light.
  • the light may be light of any suitable wavelength to result in the respective decrease or increase in pKa or pKb.
  • the source of light may be ambient light, sunlight, incandescent light, fluorescent light, LED light, laser light, and the like.
  • the light used in the present invention may The composition of the present invention utilize light within the electromagnetic spectrum ranging from infrared to visible and to ultraviolet light having wavelengths from about 1200 nm to about 200 nm. Using UV versus visible light (VIS) is not mutually exclusive as many photoactive materials have broad spectrum of absorption that covers both.
  • the suitable light may be provided from any source capable of illuminating the substrate surface.
  • ambient sunlight, incandescent light, fluorescent light, and the like may provide light of suitable wavelength.
  • the light may be provided by conventional sources such as lamps and portable or battery-powered lights.
  • specific devices may be developed or adapted for use with the compositions and method described herein.
  • a hair brush configured to incorporate LEDs that provide light of a suitable wavelength may be used to covalently modify the surface of fibers.
  • a laser may be used to provide precise targeting of the covalent modification of substrate surfaces, for example.
  • the photocatalyst is a photoacid such as, for example, an aromatic hydroxy compound, a sulfonated pyrene compound, an onium salt, a diazomethane derivative, a bissulfone derivative, a disulfuno derivative, a nitrobenzyl sulfonate derivate, a sulfonic acid ester derivative, a sulfonic acid ester of an N-hydroxyimide, or combinations thereof.
  • a photoacid such as, for example, an aromatic hydroxy compound, a sulfonated pyrene compound, an onium salt, a diazomethane derivative, a bissulfone derivative, a disulfuno derivative, a nitrobenzyl sulfonate derivate, a sulfonic acid ester derivative, a sulfonic acid ester of an N-hydroxyimide, or combinations thereof.
  • Photoacid catalysts may include, for example, hydroxy-substituted aromatics such as, for example, 8-hydroxyquinoline, 8-hydroxyquinoline sulfate, 8-quinolinol-l-oxide, 5- hydroxyquinoline, 6-hydroxyquinoline, 7-hydroxyquinoline, 5-iodo-7-sulfo-8-hydroxyquinoline, 5-fluoro-8-hydroxyquinoline, 5-fluoro-7-chloro-8-hydroxyquinoline, 5-fluoro-7-bromo-8- hydroxyquinoline, 5-fluoro-7-iodo-8-hydroxyquinoline, 7-fluoro-8-hydroxyquinoline, 5-chloro- 8-hydroxyquinoline, 5,7-dichloro-8-hydroxyquinoline, 5-chloro-7-brono-8-hydroxyquinoline, 5- chloro-7-iodo-8-hydroxyquinoline, 7-chloro-8-hydroxyquinoline, 5-bromo-8-hydroxyquinoline, 5-bromo-8-hydroxyquinoline, 5-bromo-8-hydroxyquinoline, 5-
  • Photoacid catalysts may include onium salts such as, for example, bis(4-tert- butylphenyl)iodonium perfluoro-1-butanesulfonate, diphenyliodonium perfluoro-1- butanesulfonate, diphenyliodonium-9, lO-dimethoxyanthracene-2-sulfonate, diphenyliodonium hexafluorophosphate, diphenyliodonium nitrate, diphenyliodonium p-toluenesulfonate, diphenyliodonium triflate, (4-methylphenyl)diphenylsulfonium triflate, (4- methylthiophenyl)methyl phenyl sulfonium triflate, 2-naphthyl diphenylsulfonium triflate, (4- phenoxyphenyl)diphenylsulfonium triflate
  • Photoacid catalysts may include diazomethane derivatives such as, for example, bis(benzenesulfonyl)-diazomethane, bis(p-toluenesulfonyl)diazomethane, bis(xylenesulfonyl)diazomethane, bis(cyclohexylsulfonyl)-diazomethane, bis(cyclopentylsulfonyl) diazomethane, bis(n-butylsulfonyl)diazomethane, bis(isobutylsulfonyl)- diazomethane, bis(sec-butylsulfonyl)diazomethane, bis(n-propylsulfonyl) diazomethane, bis(isopropylsulfonyl)-diazomethane, bis(tert-butylsulfonyl) diazomethane, bis(n
  • Photoacid catalysts may include glyoxime derivatives such as, for example, bis-o-(p-toluene- sulfonyl)- ⁇ -dimethylglyoxime, bis-o-(p-toluenesulfonyl)- ⁇ -diphenylglyoxime, bis-o-(p- toluenesulfonyl)- ⁇ -dicyclohexyl-glyoxime, bis-o-(p-toluenesulfonyl)-2,3-pentanedione- glyoxime, bis-o-(p-toluenesulfonyl)-2-methyl-3,4-pentane-dioneglyoxime, bis-o-(n- butanesulfonyl)- ⁇ -dimethylglyoxime, bis-o-(n-butanesulfonyl)- ⁇ -diphenylglyoxime, bis-o-(
  • Photoacid catalysts may include bissulfone derivatives such as, for example, bisnaphthylsulfonylmethane, bistrifluoromethylsulfonylmethane, Bismethylsulfonylmethane, bisethylsulfonylmethane, bispropylsulfonylmethane, bisisopropylsulfonylmethane, bis-p- toluenesulfonylmethane, bisbenzenesulfonylmethane, 2-cyclohexyl-carbonyl-2-(p- toluenesulfonyl)propane ( ⁇ -ketosulfone derivative), 2-isopropyl-carbonyl-2-(p-toluenesulfonyl) propane ( ⁇ -ketosulfone derivative).
  • Photoacid catalysts may include disulfono derivatives such as, for example, diphenyl disulf
  • Photoacid catalysts may include nitrobenzyl sulfonate derivatives such as, for example, 2,6- dinitrobenzyl p-toluenesulfonate or 2,4-dinitrobenzyl p-toluenesulfonate.
  • Photoacid catalysts may include sulfonic acid ester derivatives such as, for example, 1,2,3- tris(methanesulfonyloxy) benzene, l,2,3-tris(trifluoro-methanesulfonyloxy)benzene, or 1,2,3- tris(p-toluenesulfonyloxy)benzene.
  • sulfonic acid ester derivatives such as, for example, 1,2,3- tris(methanesulfonyloxy) benzene, l,2,3-tris(trifluoro-methanesulfonyloxy)benzene, or 1,2,3- tris(p-toluenesulfonyloxy)benzene.
  • Photoacid catalysts may include sulfonic acid esters of N-hydroxyimides such as, for example, N-hydroxysuccinimide methanesulfonate, N-hydroxysuccinimide trifluoromethanesulfonate, N- hydroxysuccinimide ethanesulfonate, N-hydroxysuccinimide 1-propanesulfonate, N- hydroxysuccinimide 2-propanesulfonate, N-hydroxysuccinimide 1-pentanesulfonate, N- hydroxysuccinimide 1-octanesulfonate, N-hydroxysuccinimide p-toluenesulfonate, N- hydroxysuccinimide p-methoxybenzenesulfonate, N-hydroxysuccinimide 2- chloroethanesulfonate, N-hydroxysuccinimide benzenesulfonate, N-hydroxysuccinimide 2,4,6- trimethyl
  • the photocatalyst is 8-hydroxyquinoline, which may act as a photoacid catalyst in lower pH solutions or as a photobase catalyst in higher pH solutions.
  • the photocatalyst is 8-hydroxy-l,3,6-pyrentrisulfonic acid trisodium salt (D&C Green 8).
  • the photocatalyst is a photobase.
  • Photobase catalysts may include derivatives of trityl alcohols such as, for example, Malachite green.
  • Photobase catalysts may also include acridine derivatives such as, for example, 9-hydroxy-10- methyl-9-phenyl-9,10-dihydroacridine.
  • Photobase catalysts may also include photoactive carbamate-containing compounds.
  • the photocatalyst may be present in the compositions and methods described herein in an amount from 0.00050 percent to 30 percent by weight relative to the total weight of the composition. Generally, there is a preferred concentration of the photocatalyst. The preferred concentration of photocatalyst depends, in part, on a variety of factors including, for example, the chemical structure of the catalyst, the reaction medium, the reaction type, and the substrate.
  • compositions described herein generally include a vehicle suitable for dispersing or dissolving the active material, the photocatalyst, and any other components to facilitate application of the active material onto the substrate surface or into the bulk portions of the substrate.
  • vehicle may comprise one or more of a solvent, an emulsifier, a surfactant, or other dispersant.
  • the properties of a suitable vehicle are dependant, at least in part, on the properties of the other components of the composition and the substrate to be modified. For example, when using in a composition intended to be applied to physiological tissues, the vehicle for that composition is selected so as not to destabilize the composition as well as avoid creating problems such as irritation or insult to the targeted physiologically tissue as well as the non-targeted surrounding tissues.
  • a suitable vehicle operates to disperse or dissolve the active material, the photocatalyst, and any other components, and to facilitate application of the active material onto the substrate surface.
  • a suitable vehicle facilitates sufficient contact between the active material and the substrate.
  • a physiologically acceptable vehicle may be any carrier, solvent, or solvent-containing composition that is suitable for application to physiological tissues such as human hair and human skin.
  • a suitable vehicle may be a solvent.
  • water is generally considered a useful solvent in consumer care products including personal care products. In various consumer care products including those of the present invention, water may be used in levels from 1% to 98% by weight of the composition. Water is particularly useful in personal care products as it does not insult physiologically tissues.
  • Additional solvent or solvent- containing vehicles include, but are not limited to, hydroxyl-containing liquids (e.g., alcohols), silicones, oils, hydrocarbons, glycols, ammonium lauryl sulfate, sodium lauryl sulfate, and combinations thereof.
  • hydroxyl-containing liquids e.g., alcohols
  • silicones oils
  • hydrocarbons e.g., glycols
  • ammonium lauryl sulfate e.g., sodium lauryl sulfate
  • sodium lauryl sulfate e.g., sodium lauryl sulfate
  • solvents, dispersants, or emulsifiers may be used as acceptable vehicles, alone or in combination with each other and/or with water.
  • a suitable vehicle is therefore generally used to dilute and/or emulsify the components forming the compositions described herein.
  • a suitable vehicle may dissolve a component (true solution or micellar solution) or a component may be dispersed throughout the vehicle (suspension, dispersion or emulsion).
  • the vehicle of suspension, dispersion or emulsion is typically the continuous phase thereof. That is, other components of the suspension, dispersion or emulsion are distributed on a molecular level or as discrete or agglomerated particles throughout the vehicle.
  • the preparation of such emulsions or dispersions of the active in these cases may be highly important. Small particles contribute to an intimate contact between the active, the substrate and the photoacid catalyst, increasing the reaction rate.
  • an emulsion that contains very small particles may be substantially more effective in providing a durable hydrophobic surface than an emulsion containing larger particles
  • compositions and methods described herein may optionally include a variety of components.
  • the compositions and methods described herein may include surfactants, emulsifiers, oxidants, reductants, pH regulators, emollients, humectants, proteins, peptides, amino acids, additive polymer or copolymers, glossers, oils and/or fatty acids, lubricants, sequestrants/chelators, antistatic agents, rheology modifiers, feel agents, fillers, dyes, pigments preservatives, perfumes, medicaments other functional components, or combinations thereof.
  • compositions and methods described herein include an oxidizing agent (oxidant).
  • oxidant may be added, for example, to render a substrate surface more amenable to photocatalytic covalent modification/functionalization in accordance with the various embodiments described herein.
  • An oxidant may be present in an amount form 0.00050% to 25% 0.1% to 10% 0.5% to 5% by weight relative to the total weight of the composition.
  • Suitable oxidants include, for example, one or more of hydrogen peroxide, urea peroxide, melamine peroxide, percarbonates, peracids, alkali metal bromates, perborates, bromates, hypochlorites, chlorites, perchlorates, iodates, periodates, permanganates and persulfates.
  • the oxidant is hydrogen peroxide.
  • reaction system The identity of the reaction system, the quantities and concentrations of reagents utilized, and the reaction conditions are all dependent, at least in part, upon the substrate to be modified, the active material utilized, and the manner in which the active material is to be associated with the substrate.
  • EXAMPLE 3Fabric Treatment by Dipping in Prototype Silicone Emulsion IA Wash and air dry a 20 cm long (4.0-gram) piece of cotton fabric.
  • EXAMPLE 4 Fabric Treatment by Spraying with Prototype Silicone Emulsion IA Wash and air dry a 20 cm long (4.0-gram) piece of cotton fabric. In a dark room, spray the fabric switch with 10.0 g of the emulsion from Example IA. Expose the fabric is to bright light (Aquarium 2OW Fluorescent tube AquaRays® Model No F20WT12-AR-FS) for 15 minute.
  • EXAMPLE I Hard Surface Treatment by Spraying with Prototype Silicone Emulsion IE Wash and air dry a 10 cm x 10 cm long white ceramic tile. In a dark room, spray the tile with 10.0 g of the emulsion from Example IE. Expose the tile to a bright light (Aquarium 2OW Fluorescent tube AquaRays® Model No F20WT 12- AR-FS) for 15 minute.
  • a bright light Aquarium 2OW Fluorescent tube AquaRays® Model No F20WT 12- AR-FS
  • Example ID In a dark room, spray the tile with 10.0 g of the emulsion from Example ID. Expose the tile to a bright light (Aquarium 2OW Fluorescent tube AquaRays® Model No F20WT 12- AR-FS) for 15 minute. Rinse the tile with a 100 mL of one to one volume ratio of methyl isobutyl ketone/toluene 3 time. Dip the tile into a fresh solution of 250 mL of this solvent mixture for 30 minutes, air dry. Upon drying, wash with Mr Clean ® cleaner, thoroughly rinse and air dry for at least 5 hours. Repeat the washing/rinsing cycle 3 times.
  • a bright light Aquarium 2OW Fluorescent tube AquaRays® Model No F20WT 12- AR-FS
  • EXAMPLE 13 Fabric Treatment by adding Prototype Silicone Emulsion ID to a Laundry Detergent Wash and air dry five 10 cm x 10 cm pieces of cotton fabric.
  • a Tide ® liquid detergent wash solution at the dilution concentration found on the product label and 100.0 g of the emulsion from Example ID. Wash the fabric with agitation for 15 minutes. Remove the fabric from the wash solution and expose to a bright light (Aquarium 2OW Fluorescent tube AquaRays® Model No F20WT12-AR-FS) for 15 minute.
  • Hard Surface Treatment by Spraying with Prototype Silicone Emulsion 1C Wash and air dry a 10 cm x 10 cm long white ceramic tile.
  • spray the tile with 10.0 g of the emulsion from Example 1C.
  • Expose the tile to a bright light (Aquarium 2OW Fluorescent tube AquaRays® Model No F20WT 12- AR-FS) for 15 minute.
  • Rinse the tile with a 100 mL of a one to one ratio by volume methyl isobutyl ketone/toluene 3 times and dip into a fresh solution of 250 mL of this solvent mixture for 30 minutes.
  • Air dry Upon drying, wash tile with Mr. Clean ® cleaner, thoroughly rinse and air dry for at least 5 hours. Repeat the washing/rinsing cycle 3 times. Repeat the procedure on a 10 cm x 10 cm piece of glass and a 10 cm x 10 cm piece of painted metal such as an automobile side panel.
  • compositions and methods described herein are primarily discussed in connection with hair, skin and fabric substrates. Nevertheless, it is recognized that the invention set forth in the following claims is not limited in application to any particular substrate. The invention set forth in the following claims may be used in connection with any substrate for which it is useful to treat the surface with the compositions and methods described herein as recognizable by one of ordinary skill in the art.
  • substrates include, for example, fabric, paper, wood, plastic, glass, tile, stone, concrete, brick, other ceramics, and composites.

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PCT/US2010/032640 2009-05-01 2010-04-28 Compositions and methods incorporating photocatalysts WO2010126919A1 (en)

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BRPI1015355A BRPI1015355A2 (pt) 2009-05-01 2010-04-28 composições e métodos de incorporação de fotocatalisadores
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Cited By (8)

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WO2011060110A1 (en) * 2009-11-13 2011-05-19 The Procter & Gamble Company Compositions and methods incorporating photocatalysts
WO2015094756A1 (en) 2013-12-19 2015-06-25 The Procter & Gamble Company Shaping keratin fibres using an amine or a diamine
WO2015094759A1 (en) 2013-12-19 2015-06-25 The Procter & Gamble Company Shaping keratin fibres using an active agent comprising at least two functional groups selected from: -c(oh)- and -c(=o)oh
WO2015094758A1 (en) 2013-12-19 2015-06-25 The Procter & Gamble Company Shaping keratin fibres using an active agent comprising a functional group selected from the group consisting of: -c(=o)-, -c(=o)-h, and -c(=o)-o-
WO2015095671A1 (en) 2013-12-19 2015-06-25 The Procter & Gamble Company Shaping keratin fibres using oxoethanoic acid and/or derivatives thereof
WO2015095685A1 (en) 2013-12-19 2015-06-25 The Procter & Gamble Company Shaping keratin fibres using 2-hydroxypropane-1,2,3-tricarboxylic acid and/or 1,2,3,4-butanetetracarboxylic acid
WO2015094837A1 (en) 2013-12-19 2015-06-25 The Procter & Gamble Company Shaping keratin fibres using carbonate ester
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WO2015094756A1 (en) 2013-12-19 2015-06-25 The Procter & Gamble Company Shaping keratin fibres using an amine or a diamine
WO2015094759A1 (en) 2013-12-19 2015-06-25 The Procter & Gamble Company Shaping keratin fibres using an active agent comprising at least two functional groups selected from: -c(oh)- and -c(=o)oh
WO2015094758A1 (en) 2013-12-19 2015-06-25 The Procter & Gamble Company Shaping keratin fibres using an active agent comprising a functional group selected from the group consisting of: -c(=o)-, -c(=o)-h, and -c(=o)-o-
WO2015095671A1 (en) 2013-12-19 2015-06-25 The Procter & Gamble Company Shaping keratin fibres using oxoethanoic acid and/or derivatives thereof
WO2015095685A1 (en) 2013-12-19 2015-06-25 The Procter & Gamble Company Shaping keratin fibres using 2-hydroxypropane-1,2,3-tricarboxylic acid and/or 1,2,3,4-butanetetracarboxylic acid
WO2015094837A1 (en) 2013-12-19 2015-06-25 The Procter & Gamble Company Shaping keratin fibres using carbonate ester
WO2015094757A1 (en) 2013-12-19 2015-06-25 The Procter & Gamble Company Shaping keratin fibres using a sugar
US11096879B2 (en) 2013-12-19 2021-08-24 The Procter And Gamble Plaza Shaping keratin fibres using an active agent comprising a functional group selected from the group consisting of: -C(=O)-, -C(=O)-H, and -C(=O)-O-
US11103434B2 (en) 2013-12-19 2021-08-31 The Procter And Gamble Company Shaping keratin fibres using carbonate ester
US11110046B2 (en) 2013-12-19 2021-09-07 The Procter And Gamble Company Shaping keratin fibres using 2-hydroxypropane-1,2,3-tricarboxylic acid and/or 1,2,3,4-butanetetracarboxylic acid
US11129784B2 (en) 2013-12-19 2021-09-28 The Procter And Gamble Company Shaping keratin fibres using oxoethanoic acid and/or derivatives thereof
US11154480B2 (en) 2013-12-19 2021-10-26 The Procter And Gamble Company Shaping keratin fibres using a sugar

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