CA2635853A1 - Responsive coated particles - Google Patents

Responsive coated particles Download PDF

Info

Publication number
CA2635853A1
CA2635853A1 CA 2635853 CA2635853A CA2635853A1 CA 2635853 A1 CA2635853 A1 CA 2635853A1 CA 2635853 CA2635853 CA 2635853 CA 2635853 A CA2635853 A CA 2635853A CA 2635853 A1 CA2635853 A1 CA 2635853A1
Authority
CA
Canada
Prior art keywords
particle
state
responsive
particles
coated particle
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
CA 2635853
Other languages
French (fr)
Other versions
CA2635853C (en
Inventor
Vladimir Gartstein
David S. Salloum
Faiz Feisal Sherman
Robert Mikhailovych Lupitskyy
Sergiy Minko
Mikhail Motornov
Roman Bogdanovych Sheparovych
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Procter and Gamble Co
Original Assignee
The Procter & Gamble Company
Vladimir Gartstein
David S. Salloum
Faiz Feisal Sherman
Robert Mikhailovych Lupitskyy
Sergiy Minko
Mikhail Motornov
Roman Bogdanovych Sheparovych
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
Application filed by The Procter & Gamble Company, Vladimir Gartstein, David S. Salloum, Faiz Feisal Sherman, Robert Mikhailovych Lupitskyy, Sergiy Minko, Mikhail Motornov, Roman Bogdanovych Sheparovych filed Critical The Procter & Gamble Company
Publication of CA2635853A1 publication Critical patent/CA2635853A1/en
Application granted granted Critical
Publication of CA2635853C publication Critical patent/CA2635853C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/11Encapsulated compositions
    • 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
    • A61K8/19Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/25Silicon; Compounds thereof
    • 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
    • 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B82NANOTECHNOLOGY
    • B82YSPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00Nanotechnology for materials or surface science, e.g. nanocomposites
    • 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
    • C08K3/00Use of inorganic substances as compounding ingredients
    • C08K3/34Silicon-containing compounds
    • C08K3/36Silica
    • 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
    • C08K9/00Use of pretreated ingredients
    • C08K9/04Ingredients treated with organic substances
    • C08K9/06Ingredients treated with organic substances with silicon-containing compounds
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09CTREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/28Compounds of silicon
    • C09C1/30Silicic acid
    • C09C1/3072Treatment with macro-molecular organic compounds
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09CTREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/28Compounds of silicon
    • C09C1/30Silicic acid
    • C09C1/309Combinations of treatments provided for in groups C09C1/3009 - C09C1/3081
    • 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
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41Particular ingredients further characterized by their size
    • A61K2800/412Microsized, i.e. having sizes between 0.1 and 100 microns
    • 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
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41Particular ingredients further characterized by their size
    • A61K2800/413Nanosized, i.e. having sizes below 100 nm
    • 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
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/57Compounds covalently linked to a(n inert) carrier molecule, e.g. conjugates, pro-fragrances
    • CCHEMISTRY; METALLURGY
    • C01INORGANIC CHEMISTRY
    • C01PINDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00Particle morphology
    • C01P2004/50Agglomerated particles
    • CCHEMISTRY; METALLURGY
    • C01INORGANIC CHEMISTRY
    • C01PINDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00Particle morphology
    • C01P2004/60Particles characterised by their size
    • C01P2004/61Micrometer sized, i.e. from 1-100 micrometer
    • CCHEMISTRY; METALLURGY
    • C01INORGANIC CHEMISTRY
    • C01PINDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00Particle morphology
    • C01P2004/60Particles characterised by their size
    • C01P2004/62Submicrometer sized, i.e. from 0.1-1 micrometer
    • CCHEMISTRY; METALLURGY
    • C01INORGANIC CHEMISTRY
    • C01PINDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00Particle morphology
    • C01P2004/60Particles characterised by their size
    • C01P2004/64Nanometer sized, i.e. from 1-100 nanometer
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/29Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982Particulate matter [e.g., sphere, flake, etc.]
    • Y10T428/2991Coated
    • Y10T428/2993Silicic or refractory material containing [e.g., tungsten oxide, glass, cement, etc.]
    • Y10T428/2995Silane, siloxane or silicone coating
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/29Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982Particulate matter [e.g., sphere, flake, etc.]
    • Y10T428/2991Coated
    • Y10T428/2998Coated including synthetic resin or polymer
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/31Surface property or characteristic of web, sheet or block
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/31504Composite [nonstructural laminate]
    • Y10T428/31652Of asbestos
    • Y10T428/31663As siloxane, silicone or silane

Abstract

A responsive coated particle comprising at least one particle comprising an interfacial surface to which a responsive coating attaches, said responsive coating comprising (a) at least one silicone-based, substantially hydrophobic polymer and (b) at least one substantially hydrophilic polymer wherein said responsive coating particle is in a first state.

Description

RESPONSIVE COATED PARTICLES

FIELD OF THE INVENTION
The present invention relates to a responsive coating provided. over the interfacial surface of a particle. Particularly, the invention relates to a responsive coating comprising at least one substantially hydrophobic and at least one substantially hydrophilic polymer formed on a particle's interfacial surface. More particularly, the invention relates to a responsive coating that can switch from a first state to at least a second state, e.g., from a substantially hydrophilic state to a substantially hydrophobic state, upon exposure to an external stimulus, a change in an environmental condition, or time.

BACKGROUND OF THE INVENTION
Interactions at the solid/liquid interface, such as protein adsorption, cell adhesion, and bio-fouling, may be determined by the outermost surface of a substrate. In order to improve a product's interfacial properties, it is desirable to enhance or prevent wetness attributes associated with a particular substrate. For example, it has been desirable to advance technologies concerning wettability properties of particular products such as feminine care and incontinence articles, baby care products, fabric care products and generally, disposable articles in order to improve comfort. Many techniques have been employed to address these concerns but have failed to provide a commercially viable substrate that provides a diverse use within consumer care products.
For example, the Nanopin film was developed around 2005 possessing highly unusual hydrophobic properties. Such technology is characterized as having a"Lotus-Effect" whereby the surface exhibits a hydrophobic characteristic, i.e., extremely poor wettability characteristics and high liquid contact angles. A droplet of water that contacts the surface of the Nanopin film forms an almost perfect sphere with a wet contact angle of approximately 178 .
While hydrophobic surfaces such as Nanopin film may offer a number of commercial advantages, coating a surface of a substrate to provide such hydrophobic conditions fails to address the commercially viable concerns of being useful for a diverse array of uses. For example, it may be desirable to form or coat a surface to exhibit hydrophilic properties in a first instance but, upon application of an external stimulus, can switch to exhibit hydrophobic properties in a second instance. Another example may include the desire to form or coat a surface to exhibit hydrophobic properties in a final instance but requires the coating to be in an initial hydrophilic state in order to allow for a substance to disperse in an aqueous medium.
Without being bound by theory, a consumer may desire a liquid solution, comprising hydrophilic particles, to be applied over a household surface for the purposes of cleaning. Upon deposition and drying, the hydrophilic particles may switch from the first hydrophilic state to a second hydrophobic state in order to prevent bio-foul matter such as biological fluid from adhering to the surface.
In order to enhance the wetness properties of a substrate for commercial use as shown above, there must be a teaching that allows for such occurrence of switching between hydrophilic and hydrophobic states, particularly upon application of an external stimulus and/or change in an environmental condition. Since the prior art fails to disclose such structures, much less methods of forming them, the present invention overcomes such deficiencies and shortcomings by the particles disclosed herein.

SUMMARY OF THE INVENTION
The present invention relates to a responsive coated particle comprising at least one particle comprising an interfacial surface to which a responsive coating attaches, said responsive coating comprising (a) at least one silicone-based, substantially hydrophobic polymer and (b) at least one substantially hydrophilic polymer wherein said responsive coating particle is in a first state.
DETAILED DESCRIPTION OF THE INVENTION
While the specification concludes with the claims particularly pointing out and distinctly claiming the invention, it is believed that the present invention will be better understood from the following description.
All percentages, parts and ratios are based upon the total weight of the compositions of the present invention, unless otherwise specified. All such weights as they pertain to listed ingredients are based on the active level and, therefore; do not include solvents or by-products that may be included in commercially available materials, unless otherwise specified. The term "weight percent" may be denoted as "wt.%" herein. Except where specific examples of actual measured values are presented, numerical values referred to herein should be considered to be qualified by the word "about".
All molecular weights as used herein are weight average molecular weights expressed as grams/mole, unless otherwise specified.
As used herein, "comprising" means that other steps and other ingredients which do not affect the end result can be added_ This term encompasses the terms "consisting of' and "consisting essentially of'. The compositions and methods/processes of the present invention can comprise, consist of, and consist essentially of the essential elements and limitations of the invention described herein, as well as any of the additional or optional ingredients, components, steps, or limitations described herein.
The ternz "substrate" as used herein refers to any organic, inorganic, synthetic, or non-synthetic surface. Examples of a substrate include, but are not limited to, a semiconductor wafer, skin, tissue, hard and soft surfaces, cells, woven and non-woven materials, hair, clothing, textiles, and combinations thereof.
The term "particles" is understood as a single particle or an aggregate of particles.
The term "interfacial surface" as used herein refers to any region that separates a single or multi-phases. Such multi-phases include, but are not limited to, solid-liquid phase, liquid-gas phase, solid-gas phase, and solid-solid phase. While the interfacial surface of the present invention is directed to a solid-gas phase, it is understood that other phases will suffice when present.
The present invention relates to a responsive coating on a part or on the entire surface of a particle. The responsive coating is comprised of two or more polymers attached to the interfacial surface of a particle. Such particle may be used to interact with the interface of a substrate wherein wettability properties may be enhanced.
Particles of the present invention may be soft, hard, organic, inorganic, or mixtures thereof and may be selected from the group consisting of oxides, metals, and metal alloys. For example, hard, inorganic particles of the present invention may include, but are not limited to, aluminum oxide, magnesium oxide, iron, iron oxide, titanium dioxide, silica, zinc, zinc iron oxide, zinc oxide. Soft, organic particles of the present invention may include, but are not limited to, dendrimers with surface groups such as poly(amidoamine) (PAMAM) phosphorous, and polypropylenimine; silsesquioxane polymers; polystyrene; polymethyl methacrylate;
polyethylene; nylon; melamine (polymethylenemelamine); polyactide; dextran;
and chitosan.
Particles of the present invention may be selected according to their Young's Modulus value (GPa). Particles of the present invention may have a Young's Modulus value of from about 0.01 GPa to about 1000 GPa. Soft, organic particles of the present invention may have Young's Modulus value of from about 0.01 to about 10 GPa. Hard, inorganic particles of the present invention may have Young's Modulus value of from about 50 GPa to about 1000 GPa.
The responsive coated particles should be small enough so as to minimize interference with visual surface attributes of a substrate to which it may adhere.
Therefore, the particles may have a size from about I nm, from about 10 nm, from about 20 nm, or from about 50 nm and no more than about 1 m, no more than about 500 nm, no more than 250 nm, or no more than about 100 nm. The particles may also be round, platelets, elliptical, spherical, cylindrical, tubular, or irregular in shape.
The polymers of the present invention may be substantially hydrophobic, substantially hydrophilic, substantially oleophobic, substantially oleophilic, or mixtures thereof. Substantially hydrophobic polymers of the present invention may be selected from silicone groups, flouro groups, or mixtures thereof. Particularly, the silicone-based, substantially hydrophobic polymers of the present invention may comprise siloxane polymers, specifically polydimethylsiloxane (PDMS) or aminopropyl-terminated PDMS. Substantially hydrophilic polymers of the present invention may be a polyelectrolyte, specifically polyethylenimine (PEI).
Particularly, substantially hydrophilic polymers may be selected from the group consisting of polyethylene oxide and its derivatives, polyacrylamide and its derivatives, poly alkyl (acrylic) acid and its salts, polystyrene sulfonic acid and its salts, and mixtures thereof. The polymers may be attached to the particle in varying amounts. For example, 70% of the substantially hydrophobic polymers may comprise PDMS while the remaining 30% of the= substantially hydrophilic polyn--ers may comprise PEI.
Without being bourid by theory, the responsive coating of the present invention may comprise polydimethylsiloxane (PDMS) as the substantially hydrophobic polymer.
PDMS has a glass transition temperature (Tg) of approximately negative 125 C (-125 C), and a melting point (Tm) of approximately negative 40 C (-40 C). PDMS has very flexible siloxane bonds and the Tg of PDMS allows additional flexibility in the design and modification of the PDMS backbone.
For instance, functional polymers may be added to the PDMS backbone changing the Tg of PDMS. PDMS also has higher permeability to gases than most other elastomeric materials. One important feature that PDMS provides is very low surface energies that are produced from the silicone polymeric surface. PDMS has a surface energy of approximately 20 dyne/cm.
Polyethylenimine (PEI) may be selected as the substantially hydrophilic polymer due to its availability and good solubility at the desired pH. It provides the reactive groups (amine groups) for grafting to a particle surface.
The mass ratio of substantially hydrophobic polymers to substantially hydrophilic polymers may be greater than about 0.01, greater than about 0.05, greater than about 1.0, greater than about 2.0 or less than about 100, less than about 50.0, less than about 10.0, less than about 8.0, or less than about 2Ø For example, the mass ratio of substantially hydrophobic polymers to substantially hydrophilic polymers may be from about 0.01 to about 100.
The polymers of the present invention attach to the interfacial surface of a particle to form a responsive coating by means of grafting. The combination of particular elements such as the selection of polymers, the functional groups that attach to the selected polymers, and the mass ratio of the polymers are amongst various factors for programming the responsive coating of the particles of the present invention. By "programming", it is meant that the responsive coating is set by the aforementioned factors to exist in a particular state such as substantially hydrophobic, substantially hydrophilic, substantially oleophobic, substantially oleophilic, or mixtures thereof.
The "first state" is considered as the first state that the particle exists.
The states may succeed accordingly (second state, third state, ete...) thereafter. The term "responsive" is used to describe the behavior of the coated particle when exposed to a external stimulus including, but not limited to, environment, pH, polarity, temperature, and substrate surface (texture, type (solid, liquid, gas), material, etc...). The particles may be deposited on a substrate wherein the substrate will exist in a particular first state. Due to the presence of the particles on the substrate, the substrate will respond to any external stimulus to provide advantageous wettability properties.
Without being bound by theory, responsive coated particles may comprise a coating comprising PDMS and PEI wherein due to the substantially hydrophilic polymers (PEI), the coating allows the particles to be substantially in a hydrophilic first state.
When a composition comprising such particles is exposed to an external stimulus such as heat, the particles may "respond' by switching from the substantially hydrophilic first state to a substantially hydrophobic second state. These particles may be further exposed to an acidic solution with a pH of about 5.5 wherein the particle may again "respond" by switching from the substantially hydrophobic second state to a substantially hydrophilic third state.
Particles of the present invention may also be subject to reversion as part of the response or switch from one state to another. For example, a composition comprising the substantially hydrophobic particles of the present invention may be exposed to an external stimulus such as UV, pH or temperature causing the particles to switch from the first substantially hydrophobic state to a second substantially hydrophilic state. After a period of time, the particles may revert back to a substantially hydrophobic state without additional exposure to an external stimulus.
Thus, a particle of the present invention may remain in a particular state until exposure to an external stimulus. Time, however, may also act as an intentional or unintentional factor that acts as a trigger to cause the particles to switch. The response of the particles is, however, determinable by their programming. Such behavior is exemplary of the coating and thus, the responsive coated particle of the present invention.

EXAMPLES
The following examples further describe and demonstrate embodiments within the scope of the present invention. The examples are given solely for the purpose of illustration and are not to be construed as limitations of the present invention, as many variations thereof are possible without departing from the spirit and scope of the invention.

Example 1 Silica nanoparticles (particle size: 0.01411, surface area: 200:h25 m2/g) were dried in vacuum oven at 120 C for 12h and then immediately used for silanization (see below). lg of silica particles were dispersed in 200mL of toluene in an ultrasonic bath for 2h. 2mL of GPS (3-(glycidoxipropyl)trimethoxysilane) was added to the dispersion and the mixture was stirred for 12h at room temperature. Afterward, the particles were isolated from the silanization mixture by centrifugation, re-dispersed in toluene, and centrifuged again. This washing process was repeated with toluene one more time. After the final centrifugation the particles were re-dispersed in MEK
(methyl ethyl ketone) with the concentration of the particles of 1%. In the next step, GPS
modified particles (20 ml of 1% dispersion in MEK) were mixed with 4g of PDMS
(polydimethylsiloxane with amino end functional group, Mw 30K) followed by evaporation of the solvent at the temperature lower than 50 C. The polymer-particles mixture was divided into three parts. The mixtures were heated in vacuum oven at 90 C for 3h (Sample#1), 80 C for lh (Sample#2), and 70 C for lh (Sample#3) to achieve three different grafting densities of PDMS
layers. The particles were isolated by centrifugation, re-dispersed in MEK, and centrifuged again.
This washing process was repeated three times to remove non-grafted PDMS. The grafting of PEI (polyethyleneimine, Mw 25K) was performed in the same way as the grafting of PDMS, The grafting temperature was 90 C with the grafting time of 3h for each sample.
After removal of non-grafted PEI, the particles were dispersed in water at pH 2. Then pH of the mixture was adjusted to pH 5 by adding a solution of NaOH. The modified switchable particles finally exist in an aqueous dispersion.

Example 2 The synthetic procedure starts with the covalent grafting of GPS onto the polymethylsilsesquioxane particles (300 nm), followed by the consequent grafting of poly(dimethylsiloxane) (PDMS) and polyethyleneimine (PEI). 0.4 mL of GPS was added to a 40 mL solution of 1% particle dispersion in methyl ethyl ketone (MEK) and the mixture was stirred for 12 hours at room temperature. Afterward, the particles were isolated. from the silanization mixture by centrifugation, re-dispersed in the MEK and centrifuged again. This washing process was repeated three more times. In the next step, the GPS-modified particles (40 mL of 1%
dispersion in the MEK) were mixed with 10% poly(dimethylsiloxane), aminopropyl terminated (Mw 30000). The mixture was heated in a water bath at 70 C for 6 hours while being vigorously stirred. After that, the dispersion was washed of its unreacted polymer by the centrifugation process described above. PDMS-grafted particle dispersion (1 % in MEK) was divided into four parts. Each part was mixed with water free, PEI (Mw 25000) at a concentration of 10% by weight. The mixtures were heated in a water bath at 70 C while being vigorously stirred for a variety of times in order to achieve different PEI layer grafting densities.
The particles were washed of unreacted PEI by the centrifugation process described above and then dispersed in Millipore water containing 1% solids by weight.

The dimensions and values disclosed herein are not to be understood as being strictly limited to the exact numerical values recited. Instead, unless otherwise specified, each such dimension is intended to mean both the recited value and a functionally equivalent range surrounding that value. For example, a dimension disclosed as "40 rnm" is intended to mean "about 40 mm".
All documents cited in the Detailed Description of the Invention are, in relevant part, incorporated herein by reference; the citation of any document is not to be construed as an admission that it is prior art with respect to the present invention. To the extent that any meaning or definition of a term in this document conflicts with any meaning or definition of the term in a document incorporated herein by reference, the meaning or definition assigned to the term in this document shall govern.
While particular embodiments of the present invention' have been illustrated and described, it would be obvious to those skilled in the art that various other changes and modifications can be made without departing from the spirit and scope of the invention. It is therefore intended to cover in the appended claims all such changes and modifications that are within the scope of this invention.

Claims (10)

1. A responsive coated particle comprising at least one particle comprising an interfacial surface to which a responsive coating attaches, said responsive coating comprising:
a. at least one silicone-based, substantially hydrophobic polymer; and b. at least one substantially hydrophilic polymer wherein said responsive coating particle is in a first state.
2. The responsive coated particle of claim 1, wherein the silicone-based, substantially hydrophobic polymer comprises PDMS and wherein the substantially hydrophilic polymer comprises PEI.
3. The responsive coated particle of any of the preceding claims, wherein the first state is a substantially hydrophilic state.
4. The responsive coated particle of any of the preceding claims, wherein the first state is a substantially hydrophobic state.
5. The responsive coated particle of any of the preceding claims, wherein the mass ratio of the silicone-based, substantially hydrophobic polymer to the substantially hydrophilic polymer is from about 0.01 to about 100.
6. The responsive coated particle of any of the preceding claims, wherein the particle is from about 1 nm to about 1 µm.
7. The responsive coated particle of any of the preceding claims, wherein the particle has a Young's Modulus value of from about 0.01 GPa to about 1000 GPa.
8. The responsive coated particle of any of the preceding claims, wherein the particle is selected from a soft, organic particle with a Young's Modulus value of from about 0.01 GPa to about 10 GPa or a hard, inorganic particle with a Young's Modulus value of from about 50 GPa to about 1000 GPa.
9 9. A method of switching the responsive coated particle of any of the preceding claims from said first state to at least a second state, said method comprising the steps of:
a. providing the responsive coated particle to a first environment; and b. exposing at least one external stimulus to said responsive coated particle wherein said external stimulus causes the responsive coated particle to switch from said first state to said second state.
10. The method of any of the preceding claims, wherein the particles revert from a second state to a first state due to time and without exposure to an additional stimulus.
CA 2635853 2006-02-14 2007-02-09 Responsive coated particles Expired - Fee Related CA2635853C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US77304606P 2006-02-14 2006-02-14
US60/773,046 2006-02-14
PCT/US2007/003540 WO2007095106A1 (en) 2006-02-14 2007-02-09 Responsive coated particles

Publications (2)

Publication Number Publication Date
CA2635853A1 true CA2635853A1 (en) 2007-08-23
CA2635853C CA2635853C (en) 2013-07-09

Family

ID=38117609

Family Applications (1)

Application Number Title Priority Date Filing Date
CA 2635853 Expired - Fee Related CA2635853C (en) 2006-02-14 2007-02-09 Responsive coated particles

Country Status (8)

Country Link
US (1) US7695814B2 (en)
EP (1) EP1984466B1 (en)
JP (1) JP5133903B2 (en)
CN (2) CN101384679B (en)
CA (1) CA2635853C (en)
ES (1) ES2621210T3 (en)
PL (1) PL1984466T3 (en)
WO (1) WO2007095106A1 (en)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8080024B2 (en) * 2005-04-28 2011-12-20 Ams Research Corporation Protective enclosure for medical device components
US9376648B2 (en) * 2008-04-07 2016-06-28 The Procter & Gamble Company Foam manipulation compositions containing fine particles
US8870839B2 (en) 2008-04-22 2014-10-28 The Procter & Gamble Company Disposable article including a nanostructure forming material
WO2011094588A2 (en) * 2010-01-29 2011-08-04 Pine David J Lock and key colloids and methods of manufacture
EP2404866A1 (en) 2010-07-09 2012-01-11 Leibniz-Institut für Polymerforschung Dresden e.V. Switchable surfaces based on freely floating colloidal particles
FR2967924B1 (en) * 2010-11-30 2014-10-31 Seb Sa NANOCHARGE OF A METAL OXIDE, PROCESS FOR THE SYNTHESIS AND USE THEREOF IN ANTI-ADHESIVE COATING BASED ON FLUOROCARBON RESIN
WO2014097309A1 (en) 2012-12-17 2014-06-26 Asian Paints Ltd. Stimuli responsive self cleaning coating
US10794850B2 (en) 2014-03-25 2020-10-06 The Procter & Gamble Company Apparatus for sensing environmental pH changes
US10782261B2 (en) * 2014-03-25 2020-09-22 The Procter & Gamble Company Apparatus for sensing environmental humidity changes
US10788439B2 (en) * 2014-03-25 2020-09-29 The Procter & Gamble Company Apparatus for sensing environmental moisture changes
US10788437B2 (en) * 2014-03-25 2020-09-29 The Procter & Gamble Company Apparatus for sensing environmental changes
US10914644B2 (en) 2014-03-25 2021-02-09 The Procter & Gamble Company Apparatus for sensing material strain
JP6349556B2 (en) * 2014-10-29 2018-07-04 シャープ株式会社 Hygroscopic material and dehumidifier using the same
WO2017015617A1 (en) 2015-07-23 2017-01-26 New York University Self-inflating microcapsules
DE102015225548A1 (en) * 2015-12-17 2017-06-22 Henkel Ag & Co. Kgaa Improved washing process II
CN109385894A (en) * 2017-08-08 2019-02-26 北京服装学院 A kind of composite polyolefine material and the preparation method and application thereof with intelligent surface

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3411759C1 (en) * 1984-03-30 1985-04-25 Th. Goldschmidt Ag, 4300 Essen Particles modified on their surface by hydrophilic and hydrophobic groups
US5118752A (en) 1991-10-15 1992-06-02 Ppg Industries, Inc. Vinyl polymer latex systems
JP3146678B2 (en) * 1992-08-31 2001-03-19 三菱マテリアル株式会社 Hydrophobic metal oxide powder
CN1145080A (en) 1994-03-04 1997-03-12 华盛顿大学 Block and grate copolymers and method relating thereof
US5700559A (en) * 1994-12-16 1997-12-23 Advanced Surface Technology Durable hydrophilic surface coatings
US5939485A (en) * 1995-06-19 1999-08-17 Medlogic Global Corporation Responsive polymer networks and methods of their use
US5997748A (en) * 1995-08-17 1999-12-07 The University Of Montana System for extracting soluble heavy metals from liquid solutions
US5672297A (en) * 1995-10-27 1997-09-30 The Dow Chemical Company Conductive composite articles based on expandable and contractible particulate matrices
US6254634B1 (en) * 1998-06-10 2001-07-03 Surmodics, Inc. Coating compositions
US6435665B2 (en) * 1998-06-12 2002-08-20 Eastman Kodak Company Device for controlling fluid movement
AR022140A1 (en) * 1998-12-31 2002-09-04 Kimberly Clark Co A COMPOSITION OF MATTER, A FILM AND AN ARTICLE THAT INCLUDE SUCH COMPOSITION AND THE PROCESS TO MAKE SUCH COMPOSITION
CA2327034C (en) * 1999-12-01 2007-07-17 Canon Kabushiki Kaisha Method of reforming element surface, element with reformed surface, method of manufacturing element with reformed surface, surface treatment liquid for forming reformed surface, and method of manufacturing surface treatment liquid
WO2002028912A2 (en) * 2000-10-06 2002-04-11 Carnegie Mellon University Preparation of nanocomposite structures by controlled polymerization
JP3595805B2 (en) * 2001-08-07 2004-12-02 キヤノン株式会社 Stimulus responsive composition, and image forming method and apparatus using the composition
US7020355B2 (en) * 2001-11-02 2006-03-28 Massachusetts Institute Of Technology Switchable surfaces
DE10206481C1 (en) 2002-02-14 2003-07-03 Inst Polymerforschung Dresden Rough surface with switchable, ultra-hydrophobic property, exhibits greater step change in angle of contact in comparison with that on smooth surface
US6803106B2 (en) * 2002-04-16 2004-10-12 William Henry Campbell Multi-layered macromolecules and methods for their use
US6855773B1 (en) * 2002-12-13 2005-02-15 The United States Of America As Represented By The Secretary Of The Army Polymer-based surfactants and interfacial modifier materials
GB2403920A (en) * 2003-04-30 2005-01-19 Univ Sussex Particulate emulsifiers

Also Published As

Publication number Publication date
CN101384679B (en) 2011-11-02
JP5133903B2 (en) 2013-01-30
US7695814B2 (en) 2010-04-13
ES2621210T3 (en) 2017-07-03
CA2635853C (en) 2013-07-09
CN101384679A (en) 2009-03-11
PL1984466T3 (en) 2017-07-31
EP1984466B1 (en) 2017-01-25
JP2009526903A (en) 2009-07-23
EP1984466A1 (en) 2008-10-29
US20070190327A1 (en) 2007-08-16
CN101384657A (en) 2009-03-11
WO2007095106A1 (en) 2007-08-23

Similar Documents

Publication Publication Date Title
CA2635853C (en) Responsive coated particles
Maan et al. Recent developments and practical feasibility of polymer‐based antifouling coatings
Zhou et al. Recent progress in durable and self‐healing super‐nonwettable fabrics
Bao et al. Robust superhydrophobic coating with hollow SiO2/PAA-b-PS Janus microspheres for self-cleaning and oil–water separation
Wen et al. Biomimetic polymeric superhydrophobic surfaces and nanostructures: from fabrication to applications
Teisala et al. Superhydrophobic coatings on cellulose‐based materials: fabrication, properties, and applications
WO2010018744A1 (en) Ultrahydrophobic powder, structure with ultrahydrophobic surface, and processes for producing these
Xia et al. Bio‐inspired, smart, multiscale interfacial materials
KR101411769B1 (en) Superhydrophilic coating compositions and their preparation
JP2002322299A (en) Self-cleaning surface by hydrophobic structure and method for producing the same
US20090042469A1 (en) Superhydrophilic and Superhydrophobic Powder Coated Fabric
JP6763375B2 (en) Method for Producing Oval, Needle or Rod Polymer Particles
EP1984465B1 (en) Responsive coated substrates
JP2002347159A (en) Self-cleaning surface, its manufacturing method and use thereof
JP4503086B2 (en) Superhydrophobic powder, structure having superhydrophobic surface using the same, and production method thereof
JP6168239B2 (en) Flat oval polymer particles and uses thereof
Kong et al. Robust fluorine-free superhydrophobic coating on polyester fabrics by spraying commercial adhesive and hydrophobic fumed SiO2 nanoparticles
Yang et al. Nanoparticles assembly-induced special wettability for bio-inspired materials
KR20130082217A (en) Hybrid transparent coating material having superhydrophobicity and method of the material
Huang et al. TiO2-based surfaces with special wettability–from nature to biomimetic application
Xu et al. Syntheses, mechanisms, and applications of bio-inspired self-cleaning surfaces
Deng et al. Preparation and Application of Superhydrophobic Surface Materials
JP2002241513A (en) Thermoplastic synthetic resin film
KS et al. Ramakrishna S
Bowen et al. Adhesion of Perfume-Filled Microcapsules to Model Fabric Surfaces

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20200210