EP1011609A4 - Compositions pour applications cosmetiques - Google Patents

Compositions pour applications cosmetiques

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Publication number
EP1011609A4
EP1011609A4 EP98922109A EP98922109A EP1011609A4 EP 1011609 A4 EP1011609 A4 EP 1011609A4 EP 98922109 A EP98922109 A EP 98922109A EP 98922109 A EP98922109 A EP 98922109A EP 1011609 A4 EP1011609 A4 EP 1011609A4
Authority
EP
European Patent Office
Prior art keywords
extract
peg
oil
cosmetic composition
polymer network
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.)
Withdrawn
Application number
EP98922109A
Other languages
German (de)
English (en)
Other versions
EP1011609A1 (fr
Inventor
Eyal S Ron
Barry J Hand
Lev S Bromberg
Marie Kearney
Matthew E Schiller
Peter M Ahearn
Scott Luczak
Thomas H E Mendum
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.)
Medlogic Global Corp
Original Assignee
Medlogic Global Corp
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 Medlogic Global Corp filed Critical Medlogic Global Corp
Publication of EP1011609A1 publication Critical patent/EP1011609A1/fr
Publication of EP1011609A4 publication Critical patent/EP1011609A4/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/26—Aluminium; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0212—Face masks
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/90—Block copolymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/91—Graft copolymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/04—Preparations for care of the skin for chemically tanning the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/04—Preparations for permanent waving or straightening the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54—Polymers characterized by specific structures/properties
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers

Definitions

  • the present invention relates to a cosmetic composition useful in a variety of topical and personal care products, including treatments of disorders and imperfections of the skin or other areas of the body. More particularly, the present invention is directed to a cosmetic composition comprising a poloxamer:poly(acrylic acid) polymer network that can be designed to reversibly gel over a wide range of conditions to provide a composition having a controllable range of viscosities, making it useful in a variety of cosmetic and personal care applications.
  • hydrogels such as cellulosics
  • a hydrogel is a polymer network which absorbs a large quantity of water without the polymer dissolving in water.
  • the hydrophilic areas of the polymer chain absorb water and form a gel region. The extent of gelation depends upon the volume of the solution which the gel region occupies.
  • Reversibly gelling solutions are known in which the solution viscosity increases and decreases with an increase and decrease in temperature, respectively. Such reversibly gelling systems are useful wherever it is desirable to handle a material in a fluid'state, but performance is preferably in a gelled or more viscous state.
  • a known material with these properties is a thermal setting gel using block copolymer polyols, available commercially as Pluronic ® polyols (BASF, Ludwigshafen, Germany), which is described in U.S. Patent No. 4, 188, 373. Adjusting the concentration of the polymer gives the desired liquid-gel transition.
  • concentrations of the polyol polymer of at least 18-20% by weight are needed to produce a composition which exhibits such a transition at commercially or physiologically useful temperatures.
  • solutions containing 18-20% by weight of responsive polymer are typically very viscous even in the "liquid" phase, so that these solutions can not function under conditions where low viscosity, free-flowing is required prior to transition.
  • these polymer concentrations are so high that the material itself may cause unfavorable interactions during use.
  • Another known system which is liquid at room temperature, but forms a semi- solid when warmed to about body temperature is formed from tetrafunctional block polymers of polyoxyethylene and polyoxypropylene condensed with ethylenediamine, commercially available at Tetronic ® polyols. These compositions are formed from approximately 10% to 5-% by weight of the polyol in an aqueous medium. See, U.S. Patent No. 5,252,318. Joshi, et al. in U.S. Patent No.
  • 5,252,318 reports reversible gelling compositions which are made up of a physical blend of a pH-sensitive gelling polymer (such as a cross-linked poly(acrylic acid) and a temperature-sensitive gelling polymer (such as methyl cellulose or block copolymers of poly(ethyleneoxide) and poly(propyleneoxide)).
  • a pH-sensitive gelling polymer such as a cross-linked poly(acrylic acid)
  • a temperature-sensitive gelling polymer such as methyl cellulose or block copolymers of poly(ethyleneoxide) and poly(propyleneoxide)
  • compositions including Pluronic ® and Tetronic ® polyols commercially available forms of poly(ethyleneoxide)/poly(propyleneoxide) block copolymers, significant increases in viscosity (5- to 8-fold) upon a simultaneous change in temperature and pH are observed only at much higher polymer levels.
  • Figs. 3-6 of Joshi, et al. Hoffman, et al. in WO95/24430 disclose block and graft copolymers comprising a pH-sensitive polymer component and a temperature-sensitive polymer component.
  • the block and graft copolymers are well-ordered and contain regularly repeating units of the pH-sensitive and temperature-sensitive polymer components.
  • the copolymers are described as having a lower critical solution temperature (LCST), at which both solution-to-gel transition and precipitation phase transition occur.
  • LCST critical solution temperature
  • the transition to a gel is accompanied by the clouding and opacif ⁇ cation of the solution.
  • Light transmission is reduced, which may be undesirable in many applications, where the aesthetic characteristics of the composition are of some concern.
  • the known systems which exhibit reversible gelation are limited in that they require large solids content and/or in that the increase in viscosity is less than 10- fold.
  • some known systems exhibit an increase in viscosity which is accompanied with the undesirable opacification of the composite.
  • a cosmetic compositions which incorporates a poloxamer:poly(acrylic acid) polymer network as a cosmetically acceptable carrier.
  • the polymer network comprises a poloxamer component randomly bonded to a poly(acrylic acid), or PAA, component in and aqueous-based medium, the polymer network being capable of aggregating in response to an increase in temperature.
  • the reverse thermal viscosifying poloxamer :poly(acry lie acid) polymer network includes random covalent bonding between the poly(acrylic acid) component and the poloxamer component of the network.
  • the polymer network may also include some unbound or "free" poloxamer or other additives which contribute to or modify the characteristic properties of the polymer composition.
  • the cosmetic composition includes a cosmetic agent selected to provide a preselected cosmetic effect.
  • cosmetic agent as that term is used herein, it is meant that the additive imparts a cosmetic effect.
  • a cosmetic effect is distinguishable from a pharmaceutical effect in that a cosmetic effect relates to the promoting bodily attractiveness or masking the physical manifestation of a disorder or disease.
  • a pharmaceutic seeks to treat the source or symptom of a disease or physical disorder. It is noted however, that the same additives may have either a cosmetic or pharmaceutical effect, depending upon the amounts used and the manner of administration.
  • cosmetic as that term is used herein, it is meant the cosmetic and personal- care applications intended to promote bodily attractiveness or to cover or mask the physical manifestations of a disorder or disease.
  • Cosmetics include those products subject to regulation under the FDA cosmetic guidelines, as well as sunscreen products, acne products, skin protectant products, anti-dandruff products, and deodorant and antiperspirant products.
  • gelation or viscosification, as that term is used herein, it is meant a drastic increase in the viscosity of the polymer network solution. Gelation is dependent on the initial viscosity of the solution, but typically a viscosity increase in the range of 2- to 100-fold, and preferably 5- to 50-fold, and more preferably 10- to 20-fold is observed in the polymer network which is used in the preparation of the cosmetic compositions of the invention. Such effects are observed in a simple polymer network solution and the effect may be modified by the presence of other components in the cosmetic composition.
  • poly(ethyleneoxide)-poly(propyleneoxide)-poly(ethyleneoxide) blocks is a triblock copolymer derived from poly(ethyleneoxide)-poly(propyleneoxide)-poly(ethyleneoxide) blocks.
  • the poloxamer is capable of responding to a change in temperature by altering its degree of association and/or agglomeration.
  • the aggregation may be in the form of micelle formation, precipitation, labile cross-linking or other factors.
  • the poly(acrylic acid) component includes poly(acrylic acid) and its salts.
  • the poly(acrylic acid) supports and interacts with the poloxamer component so that a multi- material, responsive polymer network is formed.
  • the interaction of the poloxamer and poly(acrylic acid) exhibits a synergistic effect, which magnifies the effect of the poloxamer component in viscosifying and/or gelling the solution.
  • a typical reversibly gelling polymer network may be comprised of less than about 4 wt% of total polymer solids (e.g., poloxamer and poly(acrylic acid)) and even less than 1 wt% total polymer solids while still exhibiting reverse thermal viscosification.
  • the total solids content including additives of a reversibly gelling polymer network composition may be much higher.
  • the viscosity of the gel increases at least ten-fold with an increase in temperature of about 5°C at pH 7 and 1 wt% polymer. Viscosity increases may be even greater over a larger temperature range at pH 7 and 1 % polymer network content.
  • the relative proportion of poloxamer and poly (acrylic acid) may vary dependent upon the desired properties of the polymer composition. In one embodiment, the poloxamer is present in a range of about 1 to 20 wt% and the poly (acrylic acid) is present in a range of about 99 to 80 wt% . In another embodiment, the poloxamer component is present in a range of about 79 to 60 wt% .
  • the poloxamer component is present in a range of about 41 to 50 wt% . In another embodiment, the poloxamer component is present in a range of about 51 to 60 wt% and the poly (aery lie acid) component is present in a range of about 49 to 40 wt%. In yet another embodiment, the poloxamer component is present in a range of about 61 to 90 wt% and the poly(acrylic acid) component is present in a range of about 39 to 20 wt%. In another embodiment, the poloxamer component is present in a range of about 81 to 99 wt% and the poly(acrylic acid) component is present in a range of about 10 to 1 wt% .
  • the poloxamer:poly(acrylic acid) polymer network described above is included in a cosmetic composition to improve the flow characteristics, thickness and other properties of the composition.
  • the composition includes additional cosmetic agents, such as are needed for the cosmetic purpose of the composition.
  • Additives also may be included to modify the polymer network performance, such as to increase or decrease the temperature of the liquid-to-gel transition and/or to increase or decrease the viscosity of the responsive polymer composition.
  • the poloxamer:poly(acrylic acid) polymer network is incorporated into a cosmetic composition to impart thickening properties to the cosmetic composition at the use and/or application temperature. Such thickening properties include enhanced overall viscosity, as well as a desirable viscosity response with temperature.
  • the polymer network may be useful as a thickener in pH ranges where other thickeners are not effective.
  • the poloxamer:poly(acrylic acid) polymer network is incorporated into a cosmetic composition to stabilize and solubilize hydrophobic agents in the cosmetic composition.
  • the polymer network may be included to increase emulsion stability. Many emulsions, i.e., suspension of small droplets or particles of a first material in a second material, lose viscosity upon heating. As will be demonstrated herein, the poloxamer:poly(acrylic acid) polymer network retains its emulsifying properties even with temperature increase.
  • composition may be included in the composition to impart emolliency to the composition.
  • the composition may also act as a film-forming agent after it has been applied to the skin. This film-forming agent may be used as a barrier to prevent water loss from the skin which contributes to the moisturization of the skin.
  • the poloxamer: poly (aery lie acid) polymer network may be included as an additive in cosmetic applications to prevent viscosity loss at elevated temperatures.
  • FIG. 1 is a graph of viscosity vs. temperature for a 1 wt%, 2 wt% , and 3 wt% responsive polymer network aqueous composition of a poloxamer:poly(acrylic acid) (1:1) at pH 7.0 measured at a shear rate of 0.44 sec 1 ;
  • FIG. 2 is a graph of viscosity vs. temperature for a 1 wt% poloxamer:poly(acrylic acid) polymer network composition demonstrating reversibility of the viscosity response;
  • FIG. 3 shows the viscosity response of a 2 wt% poloxamer: poly (aery lie acid) polymer composition at various shear rates;
  • FIG. 4 shows a viscosity response curve for a 2 wt% poloxamer:poly(acrylic acid) polymer network composition prepared with nominal mixing and stirring and prepared using high shear homogenization (8000 rpm, 30 min);
  • FIG. 5 is a graph of viscosity vs. temperature for a 1 wt% poloxamer :poly(acry lie acid) polymer network composition at various pHs;
  • FIG. 6 is a graph of viscosity vs. temperature for a 1 wt% poloxamer:poly(acrylic acid) polymer network composition with and without addition of 0.25 wt% KCl;
  • FIG. 7 is a graph of viscosity vs. temperature for a 1 wt% poloxamer:poly(acrylic acid) polymer network composition with and without addition of 0.5 wt% acetamide ME A;
  • FIG. 8 is a graph of viscosity vs. temperature for a 1 wt% poloxamer:poly(acrylic acid) polymer network composition without and with 5 wt%, 10 wt% and 20 wt% added ethanol, respectively;
  • FIG. 9 is an illustration of a reversibly gelling polymer network used as an emulsifier and stabilizer for a hydrophobic agent
  • FIG. 10 is a schematic illustration of the poloxamer:poly(acrylic acid) polymer network below and above the transition temperature illustrating the aggregation of the hydrophobic poloxamer regions;
  • FIG. 11 is a graph of viscosity vs. pH for a 1 wt% responsive polymer network aqueous composition of a poloxamer/poly (aery lie acid) (1: 1) measured at a shear rate of 0.44 sec 1 ;
  • FIG. 12 is a plot of viscosity vs. temperature for (a) a 1 wt% responsive polymer network aqueous composition of Pluronic ® F127 poloxamer: poly (acrylic acid) (1:1) and (b) a 1 wt% physical blend of Pluronic ® F127 poloxamer:poly(acrylic acid) (1:1) at pH 7.0 measured at a shear rate 0.22 sec 1 ;
  • FIG. 12 is a plot of viscosity vs. temperature for (a) a 1 wt% responsive polymer network aqueous composition of Pluronic ® F127 poloxamer: poly (acrylic acid) (1:1) and (b) a 1 wt% physical
  • FIG. 13 is a plot of viscosity vs. temperature for a 1 wt% responsive polymer network aqueous composition of Pluronic ® F88 poloxamer:poly(acrylic acid) (1:1) in deionized water at pH 7.0 measured at shear rate of 22 sec 1 ;
  • FIG. 15 is a plot of viscosity vs. temperature for a responsive polymer network composition of 2 wt% Pluronic ® F123 poloxamer:poly(acrylic acid) (1 : 1) at pH 7.0 measured at a shear rate of 22 sec 1 ;
  • FIG.16 is a plot of viscosity vs. temperature for 1 wt% made of series of poloxamers and poly(acrylic acid) (1:1) in deionized water at a shear rate of 132 sec 1 ;
  • FIG. 17 is a plot showing release of hemoglobin from a poloxamer:poly(acrylic acid) polymer network of the invention.
  • FIG. 18 is a plot showing the release of lysozyme from the poloxamer:poly(acrylic acid) polymer complex of the invention.
  • FIG. 19 is a plot showing release of insulin from a poloxamer:poly(acrylic acid) polymer network composition of the invention
  • FIG. 20 is a plot of viscosity vs. temperature for a poloxamer:poly(acrylic acid) polymer network composition (a) before and (b) after sterilization by autoclave;
  • FIG. 21 is a plot of viscosity vs. temperature for an oil-free moisturizing formulation prepared form (a) a responsive polymer network composition of the invention and (b) a convention oil-in-water formulation;
  • FIG. 22 is a plot of equilibrium solubility of estradiol (A, B) and progesterone
  • FIG. 23 is a plot of the ratio of equilibrium solubilities of estradiol in responsive polymer network and water vs. polymer concentration in the responsive polymer network solutions;
  • FIG. 24 is a plot of the effect of loading fluorescein on the onset of gelation of responsive polymer network vs. total polymer concentration in responsive polymer network solution (pH 7.0);
  • FIG. 25 is a plot of the percentage of (a) estradiol and (b) progesterone release from responsive polymer network vs. time;
  • FIG. 26 is a plot of the rate of progesterone release and macroscopic viscosity vs. polymer concentration;
  • FIG. 27 is a plot of the percentage of progesterone release vs. polymer concentration in responsive polymer network; and FIG. 28 is a plot of the relative diffusivity of poly(styrene) latex particles in water and responsive polymer network.
  • the present invention is directed to a cosmetic composition
  • a cosmetically acceptable carrier comprising a novel poloxamer:poly(acrylic acid) polymer network.
  • the polymer network functions as a temperature sensitive thickening agent, and in addition possesses surfactant and emulsifying capabilities which may be beneficial to the cosmetic composition.
  • the polymer network composition according to the invention includes a poloxamer component randomly bonded to a poly(acrylic acid) component. The two polymer component may interact with one another on a molecular level.
  • the polymer network contains about 0.01 - 20 wt% each of poloxamer and poly (acrylic acid).
  • Exemplary polymer network compositions range from about 1 :10 to about 10:1 poloxamer:poly(acrylic acid).
  • Polymer network gel compositions which exhibit a reversible gelation at body temperature (25-40°C) and/or at physiological pH (ca. pH 3.0-9.0) and even in basic environment up to pH 13 (hair care) are particularly preferred for cosmetic applications.
  • a 1:1 poloxamer: poly (acrylic acid) polymer network at appropriate pH exhibits flow properties of a liquid at about room temperature, yet rapidly thickens into a gel consistency of at least about five times greater, preferably at least about 10 times greater, and even more preferably at least about 30 times and up to 100 times greater, viscosity upon increase in temperature of about 10 °C and preferably about 5°C.
  • the reversibly gelling polymer network of the present invention exhibit gelation even at very low polymer concentrations.
  • polymer network compositions at pH 7 comprising about 0.5 wt% poloxamer component and about 0.5 wt% PAA exhibits a significant increase in viscosity from a free-flowing liquid (50 cps) to a gel (6000 cps).
  • the observed gelation takes place at low solids contents, such as less than 20 wt% or preferably less than about 10 wt% , of more preferably less than about 2.5 wt% or most preferably less than about 0.1 wt% .
  • only a small amount by weight of the polymer network need be incorporated into a cosmetic composition in order to provide the desired thickening or viscosifying effect.
  • the reverse viscosification effect at low polymer concentrations provides clear, colorless gels which are particularly well-suited to cosmetic applications. For example, very little residue is formed upon dehydration which may be important in some applications, such as in topically applied cosmetics.
  • An additional advantage of the polymer network of the invention is that it remains clear and translucent above and below the critical temperature or pH. These characteristics of the reversibly gelling polymer network make it well suited for use in cosmetic compositions.
  • the polymer network of the present invention technology may be added to cosmetic formulations to increase the thickness and viscosity of the composition.
  • the poloxamer:poly(acrylic acid) polymer network possesses hydrophobic regions capable of aggregation.
  • the aggregation of the polymer network of the present invention is temperature sensitive.
  • the inventive polymer network of the present invention may have a transition temperature (i.e., temperature of aggregation) above room temperature so that the cosmetic composition is of low viscosity at or below room temperature and is of high viscosity at or around body temperature (body temperature includes both surface and internal body temperature).
  • a composition may be prepared at low temperatures while the polymer network is in a low viscosity state.
  • a cosmetic composition comprising poloxamer:poly(acrylic acid) polymer network may be spread thinly to allow for even application, due to its low viscosity at room temperature, but will thicken and "fill" the skin contours upon warming up to body surface temperature.
  • the composition may be applied through a nozzle that provides high shear to reduce viscosity, yet the composition regains its viscosity after application to the skin. This contrasts with conventional formulations whicl ⁇ permanently lose viscosity after being subjected to high shear.
  • the composition may be formulated and applied as a liquid, spray, semi-solid gel, cream, ointment, lotion, stick, roll-on formulation, mousse, pad-applied formulation, and film-forming formulation.
  • the poloxamer:poly(acrylic acid) polymer network may also be included in a cosmetic composition for use as a stabilizing, solubilizing or emulsifying agent for a hydrophobic component of the cosmetic formulation.
  • the strong hydrophilic regions of the poloxamer resulting from aggregation and micelle formation create hydrophobic domains which may be used to solubilize and control release of hydrophobic agents. Similar micelle-based systems have been shown to protect trapped peptides against enzymatic degradation from surface enzymes.
  • the reversibly gelling polymer network of the present invention is a unique polymer composition designed to abruptly change its physical characteristics or the characteristics and properties of materials mixed therewith with a change in temperature. Without intending to be bound by any particular mechanism or chemical structure, it is believed that the structure of the polymer network involves a random bonding of the poloxamer onto the backbone of the poly(acrylic acid). A portion of the poloxamer which is present during the polymerization reaction which forms the poly(acrylic acid) is bonded to the backbone of the forming poly(acrylic acid) through hydrogen abstraction and subsequent reaction. See detailed discussion of the mechanism, below. The combination of the poly(acrylic acid) and randomly bonded poloxamer gives the composition its unique properties.
  • Any free poloxamer remaining after polymerization of PAA remains associated with the random co-polymer, resulting in a miscible composition.
  • Free poloxamer may also be present in the polymer network composition; however, its presence is not required in or der to observe reverse thermal viscosification.
  • the poly(acrylic acid) may be linear, branched and/or cross-linked.
  • Poly(acrylic acid) is capable of ionization with a change in pH of the solution.
  • ionization as that term is used with respect to poly (acrylic acid), it is meant the formation of the conjugate base of the acrylic acid, namely acrylate.
  • poly(acrylic acid) includes both ionized and non-ionized versions of the polymer. Changes in ionic strength may be accomplished by a change in pH or by a change in salt concentration.
  • the viscosifying effect of the polymer network is partly a function of the ionization of the poly(acrylic acid); however, reverse thermal gelling may occur without ionization.
  • the poloxamer possesses regions of hydrophobic character, e.g., poly(propyleneoxide) blocks, and hydrophilic character, e.g., poly(ethyleneoxide) blocks.
  • the poloxamer may be linear or branched.
  • Pluronic ® polymers are commercially available for (a) in the range of 16 to 48 and (b) ranging from 54-62.
  • One or more poloxamers may be used in the reversibly gelling polymer network composition of the present invention.
  • the reversibly gelling responsive polymer networks compositions of the present invention are highly stable and do not exhibit any phase separation upon standing or upon repeated cycling between a liquid and a gel state. Samples have stood at room temperature for more than three months without any noticeable decomposition, clouding, phase separation or degradation of gelation properties. This is in direct contrast to polymer blends and aqueous mixed polymer solutions, where phase stability and phase separation is a problem, particularly where the constituent polymers are immiscible in one another. And example of the dramatic increase in viscosity and of the gelation of the reversibly gelling polymer network compositions of the invention is shown in Figure 1'. Figure 1 is a graph of viscosity vs.
  • Figure 3 shows the viscosity response of a 2 wt% poloxamer:poly(acrylic acid) polymer composition at various shear rates. The viscosity response is consistent between 24°C and 34°C; however, the final viscosity is reduced with increasing shear rate.
  • the poloxamer:poly(acrylic acid) polymer network composition does not permanently loose viscosity after being subjected to high shear conditions.
  • the poloxamer :poly(acrylic acid) polymer network composition remains unaffected by such shear conditions as homogenization.
  • Figure 4 compares the viscosity response curve of a 2 wt% poloxamer:poly(acrylic acid) polymer composition prepared with nominal mixing (simple line) and stirring with that of a polymer composition of similar composition prepared using high shear homogenization designated by a ticked line (8000 rpm, 30 min)/ No significant decrease in viscosity is observed.
  • the responsive polymer network may also include additives for influencing the performance of the polymer composition, such as the transition temperature and the viscosity of the polymer composition above the transition temperature.
  • additives for influencing the performance of the polymer composition such as the transition temperature and the viscosity of the polymer composition above the transition temperature.
  • the following list is not intended to be exhaustive but rather illustrative of the broad variety of additives which can be used.
  • solvents e.g., 2-propanol, ethanol, acetone, 1,2- pyrrolidinone, N-methylpyrrolidinone
  • salts e.g., calcium chloride, sodium chloride, potassium chloride, sodium or potassium phosphates, borate buffers, sodium citrate
  • preservatives benzalkonium chloride, phenoxy ethanol, sodium hydroxymethylglycinate, ethylparaben, benzoyl alcohol, methylparaben, propylparaben, butylparaben, Germaben II
  • humectant/moismrizers acetamide MEA, lactimide MEA, hydrolyzed collagen, mannitol, panthenol, glycerin
  • lubricants hyaluronic acid, mineral oil, PEG-60-lanolin, PPG-12-PEG-50-lanolin, PPG-2 myristyl ether propionate
  • surfactants e.g.,
  • Surfactants may be divided into three classes: cationic, anionic, and non-ionics.
  • An example of a cationic surfactant used is ricinoleamidopropyl ethyldimonium ethosulfate (Lipoquat R).
  • Anionic surfactants include sodium dodecyl sulfate and ether sulfates such as Rhodapex CO-436.
  • Nonionic surfactants include Surfynol CT-111, TG, polyoxyethylene sorbitan fatty acid esters such as Tween 65 and 80, sorbitan fatty acid esters such as Span 65, alkylphenol ethoxylates such a Igepal CO-210 and 430, dimethicone copolyols such as Dow Corning 190, 193, and Silwet L7001.
  • polymers including xanthan gum, cellulosics such as hydroxyethylcellulose (HEC), carbomethoxycellulose (CMC), lauryldimonium hydroxypropyl oxyethyl cellulose (Crodacel QL), hydroxypropylcellulose (HPC), and hydroxypropylmethylcellulose (HPMC), poly (acrylic acid), cyclodextrins, methyl acrylamido propyl triammonium chloride (M APT AC), polyethylene oxide, polyvinylpyroliddone, poly vinyl alcohol, and propylene oxide/ethylene oxide random copolymers. Poloxamers may also be used as additives.
  • HEC hydroxyethylcellulose
  • CMC carbomethoxycellulose
  • Crodacel QL lauryldimonium hydroxypropyl oxyethyl cellulose
  • HPC hydroxypropylcellulose
  • HPMC hydroxypropylmethylcellulose
  • M APT AC methyl acrylamido propyl tri
  • Examples include both the Pluronic ® polyols having an (P ⁇ ) a (P 2 ) b (P ⁇ ) a structure such as Pluronic ® F38, L44, P65, F68, F88, L92, P103, P104, P105, F108, L122, and F127, as well as the reverse Pluronic ® R series (P 2 ) a (P ⁇ ) b (P 2 ) a strucmre such as Pluronic ® 17R2 and 25R8.
  • Other miscellaneous materials include propyleneoxide, urea, triethanolamine, alkyphenol ethoxylates (Iconol series), and linear alcohol alkoxylates (Plurafac series).
  • Additives affect the viscosity of the compositions differently depending upon the nature of the additive and its concentration. Some additives will affect the initial or final viscosity, whereas others will affect the temperature range of the viscosity response, or both.
  • Potassium chloride and acetamide MEA are two examples of additives which decrease the final viscosity of the composition (see Example 30).
  • KC1 (0.25%) added to a 1 wt% reversibly gelling polymer composition reduces the viscosity by about 3000 cps. See Figure 6.
  • the humectant, acetamide MEA lowers the viscosity of a 1 wt% solution by approximately 1, 500 cps (see Figure 7).
  • Glycerin, ethanol and dimethicone copolymer have been shown to affect the temperature range over which the viscosity response occurs. Glycerin shifts the transition temperature to a slightly lower range from an initial 24-34 °C to about 24- 30°C, but does not affect the final viscosity (see Example 44). The effect of ethanol on the viscosity is different at different concentration levels. At 5 wt% and 10 wt% added ethanol, the transition temperature is shifted to lower ranges, e.g., 14-19° C and 20- 29 °C, respectively. At 20 wt% added ethanol, the composition not only exhibits a lowering of the transition temperature, but also a marked increase in initial and final viscosity. See Figure 8. Dimethicone copolymer (1 wt%) also changed the transition temperature, but in this instance the transition temperature range was raised to 28- 41 °C. Thus, proper selection of additives permits the formulator to adjust the transition temperature to various ranges.
  • the polymer network compositions of the present invention may be utilized for a wide variety of cosmetic and personal care applications.
  • a cosmetic composition and effective amount of cosmetically active agent(s) which imparts the desirable cosmetic effect is incorporated into the reversibly gelling polymer network composition of the present invention.
  • the selected agent is water soluble, which will readily lend itself to a homogeneous dispersion through out the reversibly gelling polymer network composition; however, the polymer network has been demonstrated to significantly solubilize or suspend hydrophilic agents in order to improve formulation homogeneity (see Example 36). It is also preferred that the agent(s) is nonreactive with the polymer network composition.
  • the reversibly gelling polymer network compositions of the present invention may be prepared under sterile conditions.
  • An additional feature of the reversibly gelling polymer composition is that it is prepared from constiment polymers that have known accepted toxicological profiles.
  • the poloxamer:poly(acrylic acid) polymer network has been evaluated under Good Laboratory Practice (GLP) standard protocols known in the art for toxicity in animal models and found to exhibit no toxic effects.
  • GLP Good Laboratory Practice
  • the results of the toxicity study are summarized in the following Table 1.
  • the non-toxicity of the polymer network makes it an ideal candidate for use in cosmetic compositions.
  • Exemplary cosmetic and personal care applications for which the reversibly gelling polymer network composition may be used include, but are not limited to, baby products, such as baby shampoos, lotions, powders and creams; bath preparations, such as bath oils, tablets and salts, bubble baths, bath fragrances and bath capsules; eye makeup preparations, such as eyebrow pencil, eyeliner, eye shadow, eye lotion, eye makeup remover and mascara; fragrance preparations, such as colognes and toilet waters, powders and sachets; noncoloring hair preparations, such as hair conditioner, hair spray, hair straighteners, permanent waves, rinses, shampoos, tonics, dressings and other grooming aids; color cosmetics; hair coloring preparations such as hair dye, hair tints, hair shampoos, hair color sprays, hair lighteners and hair bleaches; makeup preparations such as face powders, foundations, leg and body paints, lipstick, makeup bases, rouges and makeup fixatives; manicuring preparations such as basecoats and undercoats, cuticle soften
  • the cosmetic composition may be in any form. Suitable forms include but are not limited to lotions, creams, sticks, roll-on formulations, mousses, aerosol sprays, pad-applied formulations, and film-forming formulations.
  • the foregoing list is exemplary only. Because the reversibly gelling polymer network composition of the present invention is suited for application under a variety of physiological conditions, a wide variety of cosmetically active agents may be incorporated into and administered from the polymer network composition.
  • additional cosmetically acceptable carriers may be included in the composition, such as by way of example only, emollients, surfactant, humectants, powders and other solvents.
  • the cosmetic composition also may include additional components, which serve to provide additional aspects of the cosmetic affect or to improve the stability and/or administration of the cosmetic.
  • Such additional components include, but are not limited to, preservatives, abrasives, acidulents, antiacne agents, anti-aging agents, antibacterials, anticaking, anticaries agents, anticellulites, antidandruff, antifungal, anti-inflammatories, anti-irritants, antimicrobials, antioxidants, antiperspirants, antiseptics, antistatic agents, astringents, binders, buffers, additional carriers, chelators, cell stimulants, cleansing agents, conditioners, deodorants, depilatories, detergents, dispersants, emollients, emulsifiers, enzytnes, essential oils, exfoliants, fibers, film forming agents, fixatives, foaming agents, foam stabilizers, foam boosters, fungicides, gellants, glosser, hair conditioner, hair set resins, hair sheen agents, hair waving agents, humectants, lubricants, moisture barrier agents, moisturizers, oint
  • Suitable materials which serve the additive functions listed here are well known in the cosmetic industry, a listing of the additive function and materials suitable for incorporation into the cosmetic composition may be found in Appendix A, which is appended hereto at the end of the specification. Further information may be obtained by reference to The Cosmetic Bench Handbook. Cosmetics & Toiletries, C.C. Urbano, editor, Allured Publ. Corp., 1996, which is hereby incorporated in its entirety by reference.
  • compositions of the invention include a safe and effective amount of a cosmetically active agent.
  • Safe and effective means an amount high enough to significantly positively modify the condition to be treated or the cosmetic effect to be obtained, but low enough to avoid serious side effects.
  • Preservative can be desirably incorporated into the cosmetic compositions of the invention to protect against the growth of potentially harmful microorganisms.
  • Suitable preservatives include, but are not limited to, alkyl esters of parahydroxybenzoic acid, hydantoin derivatives, parabens, propioniate salts, triclosan tricarbanilide, tea tree oil, alcohols, farnesol, farnesol acetate, hexachlorophene and quaternary ammonium salts, such as benzolconjure, and a variety of zinc and aluminum salts.
  • Cosmetic chemists are familiar with appropriate preservatives and may select that which provides the required product stability. Preservatives are preferably employed in amounts ranging from about 0.0001 % to 2% by weight of the composition.
  • Emollients can be desirably incorporated into the cosmetic compositions of the invention to provide lubricity to the formulation.
  • Suitable emollients may be in the form of volatile and nonvolatile silicone oil, highly branched hydrocarbons and synthetic esters. Amounts of emollients may be in the range of about 0.1-30 wt%, and preferably about 1-20 wt%.
  • suitable silicones include cyclic or linear polydimethylsiloxanes, polyalkylsiloxanes, polyalkylarylsiloxanes and polyether siloxanes.
  • ester emollients include alkenyl esters of fatty acids, polyhydric alcohols, such as ethyleneoxide mono and di-fatty acid esters, polyethyleneoxide and the like, ether-esters, such as fatty acid esters of ethoxylated fatty alcohols, wax esters, such as beeswax, spermaceti, mysristyl myristate and stearyl stearate, and sterol esters such as cholesterol fatty acids.
  • polyhydric alcohols such as ethyleneoxide mono and di-fatty acid esters, polyethyleneoxide and the like
  • ether-esters such as fatty acid esters of ethoxylated fatty alcohols
  • wax esters such as beeswax, spermaceti, mysristyl myristate and stearyl stearate
  • sterol esters such as cholesterol fatty acids.
  • Triglyceride esters such as vegetable and animal fats and oils. Examples include castor oil, cocoa butter, safflower oil, cottonseed oil, corn oil, olive oil, cod liver oil, almond oil, avocado oil, palm oil, sesame oil, squalene, Kikui oil and soybean oil; 2. Acetoglyceride esters, such as acetylated monoglycerides; 3. Ethoxylated glycerides, such as ethoxylated glyceryl monostearate; 4.
  • alkyl esters of fatty acids having 10 to 20 carbon atoms such as, methyl, isopropyl, and butyl esters of fatty acids, and including hexyl laurate, isohexyl laurate, isohexyl palmitate, isopropyl palmitate, decyl oleate, isodecyl oleate, hexadecyl stearate, decyl stearate, isopropyl isostearate, diisopropyl adipate, diisohexyl adipate, dihexyldecyl adipate, diisopropyl sebacate, lauryl lactate, myristyl lactate, and cetyl lactate; 5.
  • Alkenyl esters of fatty acids having 10 to 20 carbon atoms such as oleyl myristate, oleyl stearate, and oleyl oleate and the like; 6.
  • Fatty acids having 10 to 20 carbon atoms such as pelargonic, lauric, myristic, palmitic, stearic, isostearic, hydroxystearic, oleic, linoleic, ricinoleic, arachidic, behenic, and erucic acids and the like; 7.
  • Fatty alcohols having 10 to 20 carbon atoms such as, lauryl, myristyl, cetyl, hexadecyl, stearyl, isostearyl, hydroxystearyl, oleyl, ricinoleyl, behenyl, erucyl, and 2-octyl dodecanyl alcohols are examples of satisfactory fatty alcohols and the like; 8.
  • Ether-esters such as fatty acid esters of ethoxylated fatty alcohols; 10.
  • lanolin and derivative such as lanolin, lanolin oil, lanolin wax, lanolin alcohols, lanolin fatty acids, isopropyl lanolate, ethoxylated lanolin, ethoxylated lanolin alcohols, ethoxylated cholesterol, propoxylated lanolin alcohols, acetylated lanolin alcohols, lanolin alcohols linoleate, lanolin alcohols ricinoleate, acetate of lanolin alcohols ricinoleate, acetate of ethoxylated alcohols-esters, hydrogenolysis of lanolin, ethoxylated hydrogenated lanolin, ethoxylated sorbitol lanolin, and liquid and semisolid lanolin absorption bases and the like; 11.
  • Polyhydric alcohol esters such as, ethylene glycol mono and di-fatty acid esters, diethylene glycol mono- and di-fatty acid esters, polyethylene glycol (200- 6000) mono- and di-fatty acid ester, propylene glycol mono- and di-fatty acid esters, polypropylene glycol 2000 monooleate, polypropylene glycol 2000 monostearate, ethoxylated propylene glycol monostearate, glyceryl mono- and di-fatty acid esters, polyglycerol polyfatty esters, ethoxylated glyceryl monostearate, 1,2-butylene glycol monostearate, 1,2-butylene glycol distearate, polyoxyethylene polyol fatty acid ester, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters are satisfactory polyhydric alcohol esters; 12.
  • esters such as beeswax, spermaceti, myristyl myristate, stearyl stearate; 13. Beeswax derivatives, e.g., polyoxyethylene sorbitol beeswax; 14. Vegetable waxes including carnauba and candelilla waxes; 15. Phospholipids such as lecithin and derivatives; 16. Sterol including cholesterol and cholesterol fatty acid esters; 17. Amides such as fatty acid amides, ethoxylated fatty acid amides, solid fatty acid alkanolamides.
  • Humectants may be added to the composition to increase the effectiveness of the emollient, to reduce scaling, to stimulate removal of built-up scale and improve skin feel.
  • suitable humectants include polyhydric alcohols, such a glycerol, polyalkylene glycols, alkylene polyols, their derivatives, propyleneoxide, dipropyleneoxide, polypropyleneoxide, polyethyleneoxide, sorbitol, hydroxypropyl sorbitol, hexylene glycol, 1,3-butylene glycol, 1,2,6-hexanetriol, ethoxylated glycerol, prop ⁇ xylated glycerol and the like.
  • the amount of humectant may be in the range of about 0.5-30 wt% and preferably between 1-15 wt% .
  • active substances may be advantageously employed, by way of example, only suitable active agents which may be incorporated into the cosmetic composition include anti-aging active substances, anti-wrinkle active substances, hydrating or moisturizing or slimming active substances, depigmenting active substances, substances active against free radicals, anti-irritation active substances, sun protective active substances, anti-acne active substances, firming- up active substances, exfoliating active substances, emollient active substances, and active substances for the treating of skin disorders such as dermatitis and the like.
  • active agents which may be incorporated into the cosmetic composition include anti-aging active substances, anti-wrinkle active substances, hydrating or moisturizing or slimming active substances, depigmenting active substances, substances active against free radicals, anti-irritation active substances, sun protective active substances, anti-acne active substances, firming- up active substances, exfoliating active substances, emollient active substances, and active substances for the treating of skin disorders such as dermatitis and the like.
  • one or more moisturizers may be used, such as glycerin or urea, in combination with one or more precursor agents for the biosynthesis of structural proteins, such as hydroxyproline, collagen peptides, and the like.
  • ketolytic agent or an alpha-hydroxyacid such as a salicylic acid or 5-n-octanoicsalicylic acid may be used in combination with at least one liporegulating agent such as caffeine.
  • At least one keratolytic agent is used in combination with a depigmenting agent such as hydroquinone, tyrosinasee inhibitor (kosic acid), kojic acid and sodium metabisulfite and the like.
  • a depigmenting agent such as hydroquinone, tyrosinasee inhibitor (kosic acid), kojic acid and sodium metabisulfite and the like.
  • vitamin E asgainst CO 2 radicals
  • superoxide dismutase asgainst O 2 free radicals
  • sugar and caffeine asgainst OH free radicals.
  • moisturizers, sunscreens, alpha-hydroxyacids, salicylic acid or surface restructuring agents may be used in combination with enzymes for the repair of DNA, vascular protective agents or phospholipids rich in oligoelements and polyunsaturated fatty acids.
  • keratolytics such as salicylic acid, sulfur, lactic acid, glycolic, pyruvic acid, urea, resorcinol and N- acetylcysteine, and retinoids, such as retinoic acid and its derivatives may be used.
  • non-steroidal anti- inflammatory agents such as propionic acid derivatives, acetic acid, fenamic acid derivatives, biphenylcarboxylic acid derivatives, oxicams, including but not limited to aspirin, acetaminophen, ibuprofen, naproxen, benoxaprofen, flurbiprofen, fenbufen, ketoprofen, indoprofen, pirprofen, carprofen, and bucloxic acid and the like.
  • antibiotic and antimicrobials may be included in the composition of the invention.
  • Antimicrobial drugs preferred for inclusion in compositions of the present invention include salts of ⁇ -lactam drugs, quinolone drugs, ciprofioxacin, norfloxacin, tetracycline, erythromycin, amikacin, triclosan, doxycycline, capreomycin, chlorhexidine, chlortetracycline, oxy tetracycline, clindamycin, ethambutol, hexamidine isethionate, metronidazole, pentamidine, gentamicin, kanamycin, lineomycin, methacycline, methanamine, minocycline, neomycin, netilmicin, paromomycin, streptomycin, tobramycin, miconazole and amanfadine and the like.
  • suitable agents include 2-ethylhexyl p-methoxycinnamate, 2-ethylhexy N,N-dimethyl-p-aminobenzoate, p-aminobenzoic acid, 2-phenyl p-methoxycinnamate, 2-ethylhexyl octocrylene, oxybenzone, homomenthyl saliclate, octyl salicylate, 4,4'-methoxy-t- butyldibenzoylmethen, 4-isopropyl dibenzoylmethane, 3-benzylidene camphor, 3-(4-methylbenzylidene) camphor, titanium dioxide, zinc oxide, silica, iron oxide, and mixtures thereof and the like.
  • the sunscreening agents disclosed therein have, in a single molecule, two distinct chromophore moieties which exhibit different ultra-violet radiation absorption spectra.
  • One of the chromophore moieties absorbs predominantly in the UVB radiation range and the other absorbs strongly in the UVA radiation range.
  • These sunscreening agents provide higher efficacy, broader UV absorption, lower skin penetration and longer lasting efficacy relative to conventional sunscreens.
  • the sunscreens can comprise from about 0.5% to about 20% of the compositions useful herein. Exact amounts will vary depending upon the sunscreen chosen and the desired Sun Protection Factor (SPF).
  • SPF is a commonly used measure of photoprotection of a sunscreen against erythema.
  • tanning agents include, dihydroxy acetone, glyceraldehyde, indoles and their derivatives, and the like.
  • the composition may include cleansing surfactants.
  • Cleansing surfactants are cationic, anionic, amphoteric or non-ionic surfactants which are water-soluble and produce a consumer-acceptable amount of foam.
  • Non-ionic surfactants are well-known materials and have been used in cleansing compositions. Therefore, suitable non-ionic surfactants include, but are not limited to, compounds in the classes known as alkanolamides, block copolymers of ethylene and propylene, ethoxylated alcohols, ethoxylated alkylphenols, alkyl polyglycosides and mixtures thereof.
  • the non- ionic surfactant can be an ethoxylated alkylphenol, i.e., a condensation product of an alkylphenol having an alkyl group containing from about 6 to about 12 carbon atoms in either a straight chain or branched chain configuration with ethylene oxide, the ethylene oxide being present in an amount equal to at least about 8 moles ethylene oxide per mole of alkylphenol.
  • Examples of compounds of this typ include nonylphenol condensed with about 9.5 moles of ethylene oxide per mole of phenol; dodecylphenol condensed with about 12 moles of ethylene oxide per mole of phenol; dinonylphenol condensed with about 15 moles of ethylene oxide per mole of phenol; octylphenol condensed with about ten moles of ethylene oxide per mole of phenol; and diisooctyl phenol condensed with about 15 moles of ethylene oxide per mole of phenol.
  • a wide variety of acids, bases, buffers, and sequestrants can be utilized to adjust and/or maintain the pH and ionic strength of the compositions useful in the instant invention.
  • Materials useful for adjusting and/or maintaining the pH and/or the ionic strength include sodium carbonate, sodium hydroxide, hydrochloric acid, phosphoric acid, sulfuric acid, acetic acid, sodium acetate, sodium hydrogen phosphate, sodium dihydrogen phosphate, citric acid, sodium citrate, sodium bicarbonate, triethanolamine, EDTA, disodium EDTA, tetrasodium EDTA, and the like.
  • the polymer network may be useful as a solubilization agent in cosmetic and personal care applications.
  • a self-assembling system comprising the reversibly gelling polymer network exhibits thermogelation, pH sensitivity, and the ability to solubilize hydrophobic agents in aqueous media.
  • the resulting copolymer network is bioadhesive and can be applied in a number of therapies.
  • the materials described in this invention combine "reverse" thermoviscosification mucoadhesion, solubilization of hydrophobic and difficult to manage moieties, easy formulation, and protection of agents from degradation to provide a superior medium for cosmetic and personal care products.
  • the polymer network will have the ability to act as a primary emulsifier without any (or with very little) addition of traditional surfactant.
  • the responsive polymer network will also act as a stabilizer for oil soluble ingredients that would conventionally need to be solubilized by oils in formulation.
  • the hydrophobic portion of the polymer network (PPO) forms domains which act as reservoirs for an oil-soluble or hydrophobic additive, such as an oil droplet, as is illustrated in Figure 9.
  • poloxamer:poly(acrylic acid) polymer network compositions are valuable materials in the formulation of cosmetic and personal care products.
  • they may be useful as rheology modifiers, provide a cushioning effect on the skin, offer barrier properties and controlled release of actives.
  • the polymer composition may serve as a surfactant and is compatible with most ingredients used in the cosmetic industry.
  • the above properties of the poloxamer:poly(acrylic acid) polymer network provides a cosmetic composition that spreads evenly and smoothly and which leaves a lubricious feel to the skin.
  • a sensory evaluation was conducted with seven random volunteers in order to determine the sensory effect of a cream formulation on the skin.
  • An oil-free cosmetic formulation was prepared substantially as set forth in Example 33(b) and was compared to Nivea Oil Free, a product of Beiersdorf of Germany. Volunteers placed unmarked samples on the skin and evaluated the formulation based upon its feel and texture. The samples were rated on a scale of 1 (bad) to 5 (good).
  • the oil-free cosmetic formulation of the present invention scored equally to the Nivea Oil Free moisturizing product. Both samples scored a 3.5 on the rating scale.
  • the observed thermal behavior of the reversibly gelling polymer network suggests that the increase in viscosity is due to aggregation of the hydrophobic portion of the poloxamer at the transition temperature which, because of bonding with the poly(acrylic acid) component, serve as temporary cross-links which physically bridge adjacent chains of poly(acrylic acid) to provide a viscous gel-like extended polymer structure.
  • the aggregation process may be understood as occurring as shown in Figure 10, in which a backbone 20 represent poly(acrylic acid), a thin band 24 represents the hydrophobic poly(propylene) glycol region of the poloxamer and a thick band 26 represents the hydrophilic poly (ethylene glycol) region of the poloxamer.
  • a general method of making the poloxame ⁇ PAA polymer network compositions of the present invention comprises solubilization of the poloxamer in acrylic acid monomer, followed by polymerization of the monomer to PAA. Polymerization may be accomplished by addition of a polymerization initiator or by irradiation techniques.
  • the initiator may be a free radical initiator, such as chemical free radical initiators and UV or gamma radiation initiators.
  • free radical initiators may be used according to the invention, including, but in no way limited to ammonium persulfate, benzoin ethyl ether, benzyl peroxide, 1, 2'-azobis(2,4-dimethylpentanitrile) (Vazo 52) and azobisisobutyronitrile (AIBN). Initiation may also be accomplished using cationic or ionic initiators, many variations of this method will be apparent to one skilled in the art and are contemplated as within the scope of the invention.
  • the poloxamer component may be dissolved in an acrylic acid/water mixmre instead of pure monomer. It may be desirable to remove unreacted monomer and/or free poloxamer from the resultant polymer network. This may be accomplished using conventional techniques, such as, by way of example, dialysis or sohxlet extraction.
  • the scheme for bonding of poloxamer to acrylic acid may involve initiation (Eq.
  • Propagation leads to the final PAA.
  • the mechanism may proceed by initiation according to Eqs. (1) and (2), propagation to form PAA (Eq. 8), a chain transfer reaction to generate a reactive poloxamer moiety (Eq. 5), followed by addition of the reactive poloxamer moiety to the unsamrated bond of acrylic acid (Eq. 10) and subsequent propagation of the PAA chain.
  • the polymer network may include a plurality of poly (aery lie acid) units bounded to a single poloxamer unit, or alternatively, a plurality of poloxamer units bound to a single PAA backbone. Combinations of these alternatives are also a possibility.
  • Reverse phase polymerization may be used to prepare polymer network beads by dispersion of the poloxamer and acrylic acid monomer mixmre in a nonpolar solvent such as hexane or heptane.
  • the aggregating polymer /monomer solution is dispersed with 'agitation in the nonpolar solvent in order to suspend droplets of the solution.
  • Polymerization of the monomer is initiated by conventional means (i.e., addition of an initiator or irradiation) in order to polymerize the monomer and form responsive polymer network beads. See U.S.S.N.
  • Example 1 This example describes the synthesis of a polymer network and an aqueous responsive polymer network solution prepared using a triblock polymer of poly (ethyleneoxide) and poly(propyleneoxide), Pluronic ® F27 polyol, and poly (acrylic acid). This example also characterizes the gelation and the physical properties of the resultant polymer network.
  • Viscosity measurements A known amount of the resultant polymer was suspended in 100 ml deionized water into which NaOH was added. Following swelling for 3 days while stirring, the pH of the resulting fine suspension was adjusted to 7. Samples of 15 ml each were taken, and pH in each vial was adjusted to desired value by addition of 1 M HC1 or NaOH. Samples were then kept overnight and their viscosities were measured at different temperatures using Brookfield viscometer using either an SC4-18 or an SC4-25 spindle.
  • Figure 12 is a viscosity vs. temperamre graph comparing the gelling characteristics of the responsive polymer network composition and the physical blend.
  • the blend prepared by physically mixing the triblock PEG/PPG/PEG polymer and poly(acrylic acid) did not exhibit viscosifying effect either as a function of temperamre or pH. It was generally observed that 0.5 - 5 wt% polymer network compositions made of Pluronic ® F127 polyol and poly (aery lie acid) viscosity at temperatures of around 30°C and higher if pH is adjusted to 6 or higher. The gelling effect was observed in polymer network compositions standing 3 months or longer. Repeated heating and cooling of responsive polymer network compositions did not cause deterioration of the polymer network or the gelling effect. Solutions of either Pluronic ® F127 polyol or poly(acrylic acid) (1-5 wt% in water, adjusted to pH 6 or higher) or physical blends of the two lacked the reverse thermal gelling effects found for polymer network compositions.
  • Example 2 this example describes a standard operating procedure for the manufacture of the reversible gelling polymer network. The procedure is based upon a 50 liter production.
  • a NaOH solution was prepared by dissolving 131.8 g NaOH pellets in 131.8 mL DI water (50% solution). The NaOH was allowed to dissolve completely. The NaOH solution will be used to convert a percentage of the acrylic acid to sodium aery late in situ.
  • Acrylic acid monomer (4 kg) is charged into a monomer feed tank and agitated at 250 rpm. NaOH is added slowly. The precipitate formed as the acrylic acid is neutralized to sodium acrylate is allowed to dissolve.
  • Pluronic ® F 127 (3.5 kg) is slowly added to the monomer feed tank.
  • Pluronic ® F127 is dissolved under continued agitation.
  • Norpar 12 (a refined C-12 alkane) is added to the reaction vessel (37 L). The mixmre is agitated at 100 rpm.
  • Stabilizer solution of Ganex V-126 is prepared in 2L Norpar 12 and added to the reactor under agitation.
  • a reaction vessel was degassed using a nitrogen sparge introduced from the bottom of reactor and was continued throughout the reaction.
  • Initiator 13.63 g Lauryl peroxide and 4.23 g Vazo 52 in 0.7 kg acrylic acid monomer
  • the monomer solution was transferred to the reaction vessel.
  • the slurry was filtered through Buchner Funnels with filter paper (11 ⁇ m pore size) until the bulk of the Norpar had been removed from the beads.
  • the beads were washed three times with heptane.
  • the filtered beads were transferred to a Pyrex drying tray and spread on the tray in a uniform layer.
  • the beads were dried under vacuum for 4 hours at 40-50 °C.
  • the dried beads were analyzed as follows.
  • Elemental analysis The elemental analysis was performed by Quantitative Technologies, Inc., Whitehouse, NJ using a Perkin Elmer 2400 CHN Elemental Analyzer. Analysis provided C (52.49%), H (7.50%), N ( ⁇ 0.05%), the balance assumed to be oxygen (39.96%).
  • Thermal Gravimetric Analysis The TGA method was performed by Massachusetts Material Research, Inc., West Boylston, MA using a Dupont TGA model 295. The assay was run using a temperamre ramp from 30 to 500°C/min. The resolution for the system was set to 4 (1.0°C/min for all slope changes). The data was analyzed using the first derivative of the curve and using maxima and minima to mark transitions. The moisture content was also calculated in this manner.
  • the first derivative yielded three maxima.
  • the first transition (moisture) was 3.0% by weight
  • the second transition was 14.0% by weight
  • the third was 67.02% by weight. Residue (15.98%) remained.
  • the molecular weight was determined by GPC on a Hewlet Packard 1100 Liquid Chromatography system with a Viscotech T60 Triple Detector system. Three Waters Ultrahydrogel columns, 1000, 500 and 250 ⁇ , were used for the separation.
  • the mobile phase was 0.1 M NaNO 3 and 0.01 M K 2 HPO 4 salt solution, pH adjusted with phosphoric acid to a pH of 8.0 ⁇ 0.1.
  • the flow rate for the separation was 0.9 mL/min.
  • the column temperamre was maintained at 15 °C.
  • the injection volume for the assay was 50 ⁇ L.
  • a PEG molecular weight standard of 23,000 Daltons was used to align the detectors.
  • the result for the assay were: M n : 341,700 Daltons M p : 1,607,000 Daltons
  • the effect of both the bonded and non-bonded poloxamer on the gelation properties of the responsive polymer network has been determined by extraction of the non-bonded poloxamer from the material. Such extraction studies have established that the graft co-polymer alone exhibits the characteristic reverse thermal gelation of the composition; however, the presence of non-bonded poloxamer component modulates the gelation process.
  • the non-bonded poloxamer component can affect the temperamre of transition (from liquid to gel) and the degree of transition and assists in a more controlled and reproducible transition.
  • Bound poloxamer determination by ethylene oxide (EQ) titration was performed as follows. A 5 gm sample of the product polymer was extracted in dichloroethane for three hours at reflux temperatures. The solid is removed and dried under a vacuum for 12 hours at room temperamre. The dry material is then analyzed using ASTM method D 2959-95, "Standard Test Method for Ethylene Oxide Content". The amount of EO in the sample is related to the amount of poloxamer bound to the polymer. The typical result is approximately 15% by weight of EO. The relative amount of free poloxamer may be varied dependent upon the relative proportions of starting materials and the method of polymerization.
  • the residual solids presumably contain only poloxamer which is bounded to the poly(acrylic acid), i.e. , a graft co-polymer, the material still shows strong viscosification when it is neutralized and dissolved in water.
  • the temperamre of viscosification is increased substantially and the degree of viscosification per gram of total solids is increased by removal of free poloxamer.
  • the free poloxamer plays a role in modifying the extent and temperamre of viscosification.
  • the poloxamer undergoes conformational changes and changes to the critical micelle concentration as a function of temperamre.
  • the poloxamer will change from an open, non-aggregated form to a micellular, aggregated form with changes in temperamre.
  • Residual acrylic monomer determination by gas chromatography (GO.
  • the residual acrylic acid monomer was determined by GC analysis using a Hewlet Packard GC 5890A, using a HP-FFDAP-TPA 10 m x 0.52 mm x 1 ⁇ m column.
  • the sample was extracted and run in methanol. Using an internal standard ratio, the sample was compared to a one point calibration. The typical results for this assay were below 70 ppm acrylic acid monomer.
  • Residual Norpar solvent by GC Residual Norpar solvent by GC.
  • the residual Norpar in the sample was determined by GC using the above method and comparing the Norpar peaks to that of a standard. The typical results were below 1.5 wt% .
  • UV-vis spectrum Optical clarity data of UV-vis spectrophotometer was obtained. A 1.0% solution in water was prepared and measured at 420 ran. Transmittance (%) was typically greater than 90% .
  • DSC Differential scanning calorimetry
  • Example 10 The following example demonstrates the effect of hydrophilic/hydrophobic ratio on the gelling temperamre.
  • Polymer network compositions were prepared from the following poloxamers shown in Table 3.
  • the poloxamer (3.0 g) was dissolved in 3.0 g acrylic acid. The solution was deaerated by N 2 bubbling for 20 min. and following addition of the 100: 1 of freshly prepared saturated solution of ammonium persulfate in deionized water was kept at 70 °C for 16 h resulting in a strong whitish polymer. A sample of the polymer obtained (0.4 g) was suspended in 40 ml deionized water into which NaOH was added. Suspended responsive polymer network particles were allowed to dissolve under constant stirring. The resulting 1 wt% polymer network solution were subjected to the viscosity measurement at shear rate of 132 or 13.2 sec 1 using a SC4-18 spindle.
  • Example 11 The following example is related to release of and active agent from a poloxamer:poly(acrylic acid) polymer network. Drug loading and kinetics of release of the protein hemoglobin from poloxamer:poly(acrylic acid) polymer network is described.
  • Pluronic ® F127 (3.0 g) was dissolved in 3.0 g acrylic acid. The solution was deaerated by N 2 bubbling for 0.5 h and following addition of 100 FI of freshly prepared samrated solution of ammonium persulfate (Kodak) in deionized water was kept at 70° C for 16 h resulting in a transparent polymer. The resultant responsive polymer network obtained (5 g) was suspended in 95 ml deionized water into which NaOH was added. The resulting suspension was allowed to swell for 7 days. Hemoglobin loading and release.
  • Kodak ammonium persulfate
  • a 5 wt% responsive polymer network composition (3 g) was allowed to swell for 16 h in 10 ml of 0.25 mg/ml solution of human hemoglobin (Sigma) in deionized water adjusted to pH 8.
  • the resulting mixmre was well shaken and placed into the feed chambers of customized vertical, static, Franz-like diffusion cells made of Teflon.
  • the feed and receiver chambers of the diffusion cells were separated by mesh screens (#2063).
  • the receiver chamber was continuously stirred by a magnetic bar.
  • the cells were allowed to equilibrate to either 25 or 37°C (in an oven).
  • the feed and receiver phases consisted of 1 g of the hemoglobin-loaded responsive polymer network and 6 ml of phosphate-buffered saline (pH 7.4), respectively.
  • the feed phase was made of 1 g of 0.25 mg/ml hemoglobin solution.
  • the kinetic time commenced.
  • Samples of the receiver phase was withdrawn from time to time and their absorbance was measured spectrophotometrically at 400 nm.
  • corresponding calibration curves (absorbance in PBS versus hemoglobin concentration) were generated. The results of the kinetic experiment are presented in Figure 17.
  • Lysozyme loading and release A 5 wt% responsive polymer network composition (3 g) was allowed to swell for 16 h in 10 ml of 1 mg/ml solution of chicken egg-white lysozyme (Sigma) and 1.5 mg/ml sodium dodecyl sulfate (Aldrich) in deionized water adjusted to pH 8.5. The resulting mixmre was well shaken and placed into the feed chambers of customized vertical, static, Franz-like diffusion cells made of Teflon. The feed and receiver chambers of the diffusion cells were separated by mesh screens (#2063). The receiver chamber was continuously stirred by a magnetic bar. The cells were allowed to equilibrate to either 25 or 37 °C (in an oven).
  • the feed and receiver phases consisted of 1 g of the lysozyme-loaded responsive polymer network and 6 ml of phosphate-buffered saline (pH 7.4), respectively.
  • the feed phase was made of 1 g of 1 mg/ml lysozyme solution.
  • the kinetic time commenced. Samples were withdrawn and their absorbance measured spectrophotometrically at 280 nm.
  • a calibration curve was prepared for lysozyme concentration ranging from 0 mg/ml to 0.5 mg/ml in phosphate buffered saline.
  • the results of the kinetic experiment are presented in Figure 18. It can be seen that the rate of lysozyme release from the responsive polymer network composition was substantially lowered at 37 °C when compared to that at 25 °C, because of viscosity increase in responsive polymer network at elevated temperatures (see Figure 1).
  • the lysozyme released from the responsive polymer network composition was assayed using Micrococcus lysodeikticus cells and compared to that of original lysozyme.
  • the enzymatic activity of lysozyme was the same, within the error of the assay (15%), as that of the original lysozyme.
  • Control without lysozyme in presence of sodium dodecyl sulfate did not show any appreciable lysis of the cells.
  • Example 13 The following example is related to release of an active agent from a poloxamer:poly(acrylic acid) polymer network. Drug loading and kinetics of release of insulin from a responsive polymer network composition is reported.
  • a 5 wt% responsive polymer network composition (3 g) was allowed to swell for 15 h in 10 ml of 5 mg/ml solution of bovine Zi -insulin (Sigma) in deionized water adjusted to pH 7.
  • the resulting mixmre was well shaken and placed into the feed chambers of customized vertical, static, Franz-like diffusion cells made of Teflon.
  • the feed and receiver chambers of the diffusion cells were separated by mesh screens (#2063).
  • the receiver chamber was continuously stirred by a magnetic bar. the cells were allowed to equilibrate to either 25 or 37°C (in an oven).
  • the feed and receiver phases consisted of 1 g of the insulin-loaded responsive polymer network and 6 ml of phosphate-buffered saline (pH 7.4), respectively.
  • the feed phase was made of 1 g of 5 mg/ml insulin solution. After the feed solution had been loaded into the cell, the timing commenced. Samples were withdrawn and their absorbance was measured spectrophotometrically at 280 nm. A calibration curve was prepared for insulin concentration ranging from 0 mg/ml to 1.25 mg/ml in phosphate buffered saline. The results of the kinetic experiment are presented in Figure 19.
  • the rate of insulin release from responsive polymer network was substantially lowered at 37°C when compared to that at 25°C, because of viscosity increase in responsive polymer network at elevated temperatures (see Figure 1).
  • Example 14 This example demonstrates the preparation of a sterile reversibly gelling polymer network aqueous composition and the stability of the composition to sterilization.
  • the polymer network is prepared as described in Example 1 , except that the composition is prepared at 2 wt% Pluronic ® F127 polyol/poly (acrylic acid). After dissolution of the 2 wt% polymer network in water, the viscosity is measured. The composition then is sterilized by autoclaving at 121 °C, 16 psi for 30 minutes. Viscosity is determined after sterilization. The corresponding curves for viscosity (a) before and (b) after sterilization are shown in Figure 20 and establish that minimal change in the viscosity profile of the material has occurred with sterilization.
  • Examples 15-30 show additives which may be used to affect the transition temperamre overall viscosification of the polymer network composition.
  • a 1 wt% polymer network was prepared in deionized water at pH 7 in which a variety of additives were included in the composition. The effect of the additive was determined by generation of a Brookfield viscosification curve. Results are reported in Table 4.
  • Example 31 Because of the surfactant nature of the polymer network composition coupled with the gelation effect of the polymer network composition, it is possible to prepare formulations which are 100% water-based, but which are lubricous and thick.
  • Formulations including a nonionic surfactant formulation An O/W (oil-in- water) emulsion was made by combining the following ingredients utilizing conventional mixing techniques:
  • Formulations including a cationic surfactant formulation An O/W (oil-in- water) emulsion was made by combining the following ingredients utilizing conventional mixing techniques: Table 6.
  • This formulation contains a cationic surfactant and gives an emulsion that is fluid at room temperamre but viscosifies above 32 °C.
  • Formulations including an anionic surfactant formulation An O/W (oil-in- water) emulsion was made by combining the following ingredients utilizing conventional mixing techniques:
  • Example 32 An oil-free, clear, anti-acne treatment is made by combining the following ingredients utilizing conventional mixing techniques:
  • composition displays a flowable clear jelly appearance with excellent spreadability and absorption characteristics at room temperamre, and after heating the formulation to 32°C, the composition thickens to a gel-like consistency.
  • Example 33 Oil-free Moisturizer (formulation I): An oil-free, lubricous moisturizer was made by combining the following ingredients utilizing conventional mixing techniques: Table 9.
  • the above ingredients were added and processed as described above for the acne composition.
  • the composition displayed a flowable creamy lotion appearance with excellent emolliency, spreadability and absorption characteristics at room temperamre. After heating the formulation to above 26°C, the composition thickened to a gel-like consistency.
  • the viscosity vs. temperamre curve is shown in Figure 21 and demonstrates that addition of adjuvants to the composition significantly enhances the responsive polymer network maximum viscosity ( > 900.000 cps).
  • the use of the poloxamer:poly(acrylic acid) polymer network in the formulation also imparts a unique viscosification effect after application to the skin, which is not evident in typical commercial O/W emulsion formulations (See Figure 21b).
  • Oil-free Moisturizer (formulation II): An oil-free, lubricous moisturizer was made by combining the following ingredients utilizing conventional mixing techniques:
  • the above ingredients were added and processed as described above for the acne composition.
  • the composition displayed a flowable creamy lotion appearance with excellent emolliency, spreadability and absorption characteristics at room temperamre. After heating the formulation to above 26 °C, the composition thickened to a gel-like consistency.
  • the addition of adjuvants to the composition significantly enhances the polymer network maximum viscosity.
  • Example 34 Sunscreen Lotion. An oil-free, lubricous sunscreen lotion was made by combining the following ingredients utilizing conventional mixing techniques:
  • the above ingredients were added and processed as described above for the acne composition.
  • the composition displayed a flowable creamy lotion appearance with excellent emolliency, spreadability and absorption characteristics at room temperamre. After heating the formulation to above 26 °C, the composition thickened to a gel-like consistency.
  • the addition of adjuvants to the composition significantly enhances the polymer network maximum viscosity.
  • Example 35 Facial mask. A face mask was made by combining the following ingredients utilizing conventional mixing techniques:
  • the above ingredients were added and processed as described above for the acne composition.
  • the composition displayed a flowable creamy lotion appearance with excellent emolliency, spreadability and absorption characteristics at room temperamre. After heating the formulation to above 26 °C, the composition thickened to a gel-like consistency.
  • the addition of adjuvants to the composition significantly enhances the polymer network maximum viscosity.
  • Example 36 Facial toner.
  • a face mask was made by combining the following ingredients utilizing conventional mixing techniques:
  • the above ingredients were added and processed as described above for the acne composition.
  • the composition displayed a flowable creamy lotion appearance with excellent emolliency, spreadability and absorption characteristics at room temperamre. After heating the formulation to above 26 °C, the composition thickened to a gel-like consistency.
  • the addition of adjuvants to the composition significantly enhances the polymer network maximum viscosity.
  • Example 36 Solubilization studies of model hydrophobic agents in the poloxamer :poly(acrylic acid) polymer network: estradiol and progesterone. This example is presented to demonstrate the solubilization of a hydrophobic agent in the polymeric network. Progesterone and estradiol were used as the hydrophobic agents in this model solubilization study.
  • Acrylic acid (99%), fluorescein (98%), ⁇ -estradiol (98%), and progesterone (98%) were all obtained from Aldrich and used as received.
  • Pluronic ® F127 NF was obtained from BASF.
  • Poly (oxyethylene-b-oxypropylene-b-oxyethylene)-g-poly (acrylic acid) copolymers (responsive polymer network) were synthesized by free-radical polymerization of acrylic acid in the presence of poloxamer as described above.
  • the polymer network copolymers discussed here were composed of about 1 : 1 ratio of PAA to poloxamer.
  • the rheological properties of polymer network were assessed using LVDV-II + and RVDV-II+ Brookfield viscometers.
  • the microscopic light scattering of 21 nm poly(styrene) latex particles in deionized water and 1 wt% reversibly gelling polymer network was measured using He-Ne laser as described previously (see Matsuo, E.S., Orkisz, M., Sun, S.-T., Li, Y., Tanaka, T., Macromolecules, 1994, 27, 6791).
  • the solubility of fluorescein and hormones in aqueous solutions was measured by the equilibrium of excess solubilizate with the corresponding solution following removal of undissolved species by centrifugation and filtration.
  • Hydrophobic agents were assayed spectrophotometrically at 240 (progesterone) or 280 nm (estradiol), or by using 70/30 w/w H 2 SO 4 /MeOH (Tsilifonis-Chafetz reagent).
  • In vitro hormone release studies were conducted using thermostated, vertical Franz cells. Spunbonded polypropylene microfilters (micron retention, 15-20) were used as a membrane separating feed and receiver phases in Franz cells. The responsive polymer network, water, ethanol, and 20% PEG in water were observed to wet the membrane. The receiver solution consisted of 20 w% PEG in water (pH 7) and were stirred by magnetic bars. The feed phases composed of responsive polymer network were loaded with either estradiol or progesterone. Each hormone was dissolved in ethanol and the resulting solution was added into the responsive polymer network.
  • partition coefficient P was estimated from equilibrium solubilities of estradiol in responsive polymer network and water:
  • ⁇ G -RTlnP
  • ⁇ H -R ⁇ lnP/ ⁇ (l/T)
  • ⁇ S ( ⁇ H - ⁇ G)/T (14)
  • Negative ⁇ G values indicate spontaneous solubilization at all temperatures, whereas positive ⁇ H shows that the solubilization was endothermic, similar to the solubilization of estriol, as well as indomethacin, by the poloxamer.
  • ⁇ S of solubilization was always positive, suggesting that the more ordered water molecules surrounding hydrophobic estradiol molecules moved to the less ordered bulk phase when the estradiol was transferred to the hydrophobic core of PPG segments in responsive polymer network.
  • the aggregation of the PPG segments at elevated temperatures provides not only temporary cross-linking in the gel, but also a thermodynamically "friendly" environment for the hydrophobic drugs. Indeed, one can express the free energy of formation of the aggregate core-water interface in responsive polymer network as:
  • ⁇ G [ ⁇ P w (l- ⁇ ) + ⁇ W D ⁇ ](4 ⁇ R 2 /n) (15) where ⁇ P w and ⁇ W D are the interfacial tensions between pure PPO polymer and water and between water and the drug, respectively; ⁇ is the volume fraction of the drug within the PPO core; R is the effective radius of the core; and n is the aggregation number.
  • Equation (3) shows that solubilization of a hydrophobic drug of high ⁇ W D should increase the stability of the aggregate.
  • the solubilization process was found to decrease the critical micellization concentration and substantially increase the micellar core radius in Pluronic surfactants (Hurter, P.N., et al., "In Solubilization in Surfactant Aggregates", Christian, S.D., Ed., Marcel Dekker, New York, 1995).
  • a similar trend is indicated by the lowering the onset of gelation of the responsive polymer network upon solubilization of fluorescein (LogP 2.1) ( Figure 24).
  • the solubilization of hydrophobic drugs by responsive polymer network analogous to the micellar solubilization of drugs by poloxamer, suggests that the responsive polymer network can be an effective vehicle in drug delivery.
  • Abrasive abrades, smoothes, polishes Buffer: helps maintain original pH (acidity or basicity) of a preparation
  • Absorbent powder takes up liquids, sponge-like action
  • Carrier a vehicle or base used for a preparation
  • Absorption base formes water-in-oil emulsions
  • Chelate form a complex with trace-metal impurities, usually calcium or iron
  • Acidulent acidifies, lowers pH, neutralizes alkalis
  • Colorant adds color, may be a soluble dy or an insoluble pigment
  • Amphoteric capable of reacting chemically either as an acid or a base; amphoteric Conditioner: improves condition of skin and hair surfactants are compatible with anionic and
  • Coupling agent aids in solubilization or cationic surfactants emulsification of incompatible componenets
  • Analgesic relieves pain
  • Decolorant removes color by adsorption
  • Antacid neutralizes stomach acidity bleaching or oxidaion Antibacterial: destroys/inhibits the growth/ Denaturant: used to denature ethyl alcohol reproduction of bacteria
  • Dental powder powdered dentifrice
  • Anti-caking prevents or retards caking of
  • Deodorant destroys, masks, or inhibits powders; keeps powders free-flowing formation of unpleasant odors
  • Anti-dandruff retards or eliminates dandruff
  • Detergent a surface-active agent (surfactant) that
  • Anti-inflammatory reduces, suppresses, cleans by emulsifying oils and suspends counteracts inflamation paniculate soil
  • Anti-irritant reduces, suppresses or prevents Disinfectant: destroys pathogenic irritation microorganisms
  • Antimicrobial destroys, inhibits or suppresses
  • Dispersant promotes the formation and the growth of microorganisms stabilization of a dispersion or suspension
  • Antioxidant inhibits oxidation and rancidity Dye stabilizer: see Stabilizer
  • Antiperspirant reduces or inhibits perspiration
  • Emollient softens, smoothes skin
  • Antipruritic reduces or prevents itching Emulsifier: a surface-active agent (surfactant) that promotes the formation of water-in-oil
  • Antiseptic inhibits the growth of or oil-in-water emulsions microorganisms on the skin or on living tissue
  • Enzymes complex proteins produced by living cells that catalyze biochemical reactions at
  • Antistat reduces static by neutralizing electrical body temperature. charge on a surface
  • Fiber strands of natural or synthetic polymers
  • Astringent contracts organic tissue after for instance, cotton, wool, silk, nylon, application polyester
  • Binder promotes cohesion of powders
  • Film former solution of a polymer that forms
  • Bleaching agent lightens color, oxidizing agent films when the solvent evaporates after application to a surface
  • Fixative fixes or sets perfumes; retards agent and re-establishes the disulfide evaporation; promotes longer lasting aroma linkages in hair
  • Flavor imparts a characteristic taste (and aroma)
  • Oil absorbent see Absorbent powder to edible foods and drinks; sometimes used
  • Ointment base an anhydrous mixture of in lip products oleaginous components used as a vehicle for
  • Foam booster enhances quality and quantity of medicments lather of shampoos
  • Opacifier opacfies clear liquids or solids
  • Foamer a surface-active agent (surfactant) that
  • Oxidant oxidizing agent, neutralizes reducing produces foam; an emulsion of air-in-water agents, bleaching agent Foam stabilizer: see Foam booster
  • Pearlant imparts a pearlescent texture and luster
  • Fungicide inhibits or destroys growth of fungi
  • Gellant a gelling agent; forms gels; includes a
  • Peroxide stabilizer see Stabilizer wide variety of materials such as polymers, clays and soaps
  • Pigment a finely powdered insoluble substance used to impart color, luster, or opacity Glosser: furnishes a surface luster or brightness; usually used in lip or hair products
  • Plasticizer plasticizes (makes more flexible) polymeric films or fibers
  • Polish smoothes; adds gloss and luster
  • Hair dye imparts a new permanent or semi- compound consisting of repeating structural permanent color to hair units
  • Hair-set polymer polymer and/or resins used to make hair-set polymer
  • Powder a solid in the form of fine particles maintain desired hair shape
  • Preservative protects products from spoilage by
  • Hair-set resin se Hair-set polymer microorganisms
  • Propellant pressurized gas in a container used Neutralizer to expel the contents when pressure is
  • Humectant absorbs, holds, and retains moisture released by opening a valve
  • Hydrotrope enhances water solubility
  • Protein naturally occurring complex combinations of amino acids
  • Lathering agent a surface active agent
  • surfactant that forms a foam or lather on Refatting agent: adds oils materials to the mixing with air in solution; see also Foamer surface of substrates, e.g., skin and hair
  • Lubricant reduces friction, smoothes, adds slip
  • Resin nonvolatile solid or semisolid organic substances obtained from plants as exudates
  • Moisture barrier retards passage of moisture or to prepared by polymerization of simple water molecules
  • Moisturizer aids in increasing the moisture
  • Sequestrant forms coordination complexes with content of the skin through humectant or multivalent positive ions barrier action
  • Silicone polymeric organic silicon compounds
  • Neutralizer an oxidizing agent used in hair which are water-resistant waving that stops the action of the reducing
  • Skin protectant protects the skin from products are mainly high-molecular-weight environmental hydrocarbons
  • Solubilizer solubilizes, usually into aqueous
  • Wetting agent a surface-active agent vehicles, normally insoluble materials, such (surfactant) that lowers the surface and as fragrances, flavors, oils, etc. interfacial tension, facilitating the wetting of surfaces
  • Solvent usually liquids capable of dissolving other substances
  • Stabilizer addedto stabilize emulsions and/or suspensions
  • Stimulant produces a temporary increase in the functional activity of an organism or any of its parts
  • Surfactant lowers surface tension between two or more incompatible phases; soaps, detergents, wetting agents, solubilizing agents and emulsifying agents are typical surfactants; surfactants are classified as anionic, cationic, nonionic and amphoteric; anionic surfactants are negatively charged, cationic surfactants have no electrical charge
  • Suspending agent keeps finely divided solid particles in suspension
  • Sweetener sweetens to provide a more pleasant taste
  • Tanning accelerator accelerates the tanning of skin
  • Thickener thickens or increases viscosity/ consistency
  • Thixotrope the property of certain gels and emulsions of becoming more fluid or less viscous when shaken or stirred
  • UV absorber used as a sunscreen and to protect preparations from degradation by UV radiation
  • UVA absorber absorbs in the range 320- 400 nanometers (nm)
  • UVB abosrber absorbs in the range 290- 320 nanometers (nm)
  • Wax any of numerous substances of plant, animal or synthetic origin that contain principally esters of higher fatty acids and higher fatty alcohols; free fatty alcohols, fatty acids and hydrocarbons may also be present; waxes derived from petroleum FUNCTIONS
  • Jojoba (Buxuxux chinensis) seed powder Lactic acid Luffa cylindrica Malic acid
  • Mushroom Coriolus versicolor extract Acidulent Must rose (Rosa moschata) oil
  • Pine (Pinus sylvestris) needle extract Stenocalyx micalii extract
  • Anticaking Orange blossom extract Aluminum starch octenylsuccinate Pfaffia paniculata extract
  • Butcherbroom (Ruscus aculeatus) extract Horse chestnut (Aesculia hippocastanum) extract
  • Palmitoyl collagen amino acids Undecylenoyl collagen amino acids
  • Trichomonas japonica extract Capryloyl collgen amino acids
  • Beta-carotene Aluminum zirconium tetrachlorohydrex GLY BHA Aluminum zirconium trichlorohydrate
  • Cocodimonium hydroxypropyl hydrolyzed soy Astragalus sinicus extract protein Astrocaryum murumuru, A. tucuma extract Dimethicone hydroxypropyl trimonium chloride Azadirachta indica extract dimethyl behenamine, D. cocamine Azelamide MEA
  • Linoleamidopropyl dimethylamine dimer Hops (Humulus lupulus) extract dilinoleate Horesetail extract
  • Sanguisorbae root extract Mulberry (Moras nigra) extract Selinum spp. extract Sanguisorbae root extract Shorea robusota extract Tannic acid Botanical Walnut (Juglans regia) leaf extract, oil Acacia Wheat (Triticum vulgare) protein Acacia farnesiana extract White nettle (Lamium album) extract Agrimony (Agrimonia eupatoria) extract Witch hazel (Hamamelis virginiana) extract Alder (Alnus firma) extract Xanthozylum bungeanum extract Alfalfa (Medicago sativa) extract Zinc lactate Algae (Ascophyllum nodosum) extract
  • Distarch phosphate Artichoke (Cynara scolymus) extract ethylcellulose Asafetida (Ferula assa foetida) extract
  • Octyldodecyl myristate Bearberry (Arctostaphylos uvaOursi) extract bis-Octyldodecyl stearoyl dimer dilinoleate Bee pollen extract
  • Burdock (Arctium lappa) extract Eleuthero ginseng (Acanthopanax senticossus) Burdock (Arctium minus) root extract extract
  • Butcherbroom Ruscus aculeatus extract Eucalyptus (Eucalyptus globulus) extract
  • Calamus (Acorus calamus) extract Eucommia ulmoides extract Calendula officinalis extract Euphrasia officinalis extract
  • Capsicum frutescens extract C.f. oleoresin Everlasting (Helichrysum arenarium) extract
  • Carrageenan Choondrus crispus
  • Fenugreek extract Carrot (Daucus carota) extract
  • Fermented rice Oryza sativa) extract
  • Clover Trifolium pratense extract Goldthread (Coptis japonica) extract officinale rhizome extract, Co. Gotu kola extract water Grape (Vitis vinifera) distillate, extract Coffee (Coffea arabica) bean extract Grape (Vitis vinifera) leaf, seed extract oatmeal Grape skin extract (Tussilago farfara) leaf extract Grapefruit (Citrus grandis) peel extract (Symphytum officinale) leaf extract Green bean (Phaseolus lunatus) extract extract Ground Ivy (Glechoma hederacea) extract (Echinacea angustifolia) extract Guarana (Paullinia cupana) extract officinalis Harpagophytum procumbens extract olitorius extract Hay flower extract (Coriandrum sativum) extract Hazel (Corylus aveilana) nut extract (Zea mays) cob powder, silk extract Henna (Lawsonia inermis) extract po
  • Hypericum perforatum extract Oat (Avena sativa) bran, bran extract, flour,
  • Hyssop Hyssopus officinalis
  • Jojoba (Buxus chinensis) seed powder Parsley (Caram petroselinum) extract
  • Kiwi Actinidia chinensis
  • seed oil Pea Purge sativum
  • Kola Cold oil
  • Peach Peach (Prunus persica) extract
  • leaf extract
  • Lemon (Citrus medica limonum) extract juice Peppermint (Mentha piperita) extract, oil extract, peel extract Perilla ocymoides extract
  • Licorice (Glycyrrhiza glabra) extract Pospholipids
  • Maidenhair fern extract Pollen extract magnolia kobus extract Pongamol Mallow extract Poria Cocos extract
  • Mistletoe (Viscum album) extract Rehmannia chinensis extract Mugwort (Artemisia princeps) extract, water Restharrow (Ononis spinosa) extract
  • Myrrh (Commiphora myrrha) extract Rhubarb (Rheum palmatum) extract Rice (Oryza sativa) bran extract Wild marjoram (Origanum vulgare) extract Rice fatty acid Willow (Salix alba) bark extract, extract
  • Silver fir (Abies pectinata) extract Phosphoric acid Sisal (Agave rigida) extract Potassium phosphate Slippery elm extract Potassium sodium tartrate Soapberry (Sapindus mukuross) extract Sodium acetate, S. citrate Sophora angustifolia extract Sodium lactate, S.
  • Pentasodium pentetate Oat (Avena sativa) bran extract
  • Tetrasodium EDTA chloride Tripotassium EDTA Acrylamidopropyltrimonium chloride/acrylamide
  • Aesculus chinensis extract AMP-isostearoyl hydrolyzed wheat protein Artemisia apiacea extract Apricot (Prunus armeniaca) kernel oil
  • Coccinea indica extract Behenamidopropyldimethylamine behenate
  • Euterpe precatoria extract Caprylyl pyrrolidone Ficus racemosa extract Cassia auriculata extract
  • Nelumbium speciosum extract Cocamidopropyl ethyldimonium ethosulfate
  • Ocimum basilicum extract O. santum extract
  • Cocamidopropyl PG-dimonium chloride C.P.c.
  • Dimethylamidopropylamine dimerate Isostearamidopropyl morpholine, I.m. lactate Disodium hydrogenated cottonseed glyceride
  • Isostearamidopropyl morpholine oxide sulfosuccinate Isostearamidopropyl PG-dimonium chloride
  • Distearyldimonium chloride Isostearylamidopropyl dihydroxypropyl Ethyl ester of hydrolyzed keratin dimonium chloride
  • Henna (Lawsonia inermis) extract Lauroyl hydrolyzed collagen, L.h. elastin
  • Oleamine oxide Ricinoleamidopropyl ethyldimonium ethosulfate
  • Palmitamidopropyl betaine Silk amino acids Palmitamidopropyl dimethylamine Sodium/TEA-lauroyl collagen amino acids
  • PEG-2 oleammonium chloride Sodium cocoyl hydrolyzed soy protein
  • PEG-3 lauramine oxide Sodium hydrogenated tallow dimethyl glycinate
  • Dental powder Disodium lauroamphodiacetate Dicalcium phosphate Disodium lauroamphodipropionate Silica Disodium lauryl sulfosuccinate
  • Chlorophyllin-copper complex Disodium tallowiminodipropionate
  • Palmitamidopropyl betaine Myristalkonium saccharinate PEG- 10 glyceryl stearate Shikonin
  • PPG-9 diethylmonium phosphate C12-13, C12-16, C14-15 alcohols
  • Rapeseed oil ethoxylated high eracic acid C 10-30 cholesterol/lanostearol esters
  • Triisostearin PEG-6 esters Caprylic/capric/succinic triglyceride
  • Trioctyldodecyl citrate Capsicum fratescens oleoresin Carrot (Daucus carota sativa) oil
  • Emollient Cashew (Anacardium occidentale) nut oil Acetylated glycol stearate Castor (Ricinus communis) oil
  • Cocoa butter Dioctyl malate, D. sebacate, succinate
  • Coco-caprylate/caprate Dipentaerythritol fatty acid ester Coco-rapeseedate Dipentaerythrityl hexacaprylate/hexacaprate
  • Dimethicone copolyol acetate D.c. almondate hexyl laurate hexyldecanol Dimethicone copolyol isostearate, D.c. lactate Hexyldecyl stearate Dimethicone copolyol methyl ether honey extract Dimethicone copolyol phthalate Hybrid safflower (Carthamus tinctorius) oil Dimethicone propylethylenediamine behenate Hybrid sunflow (Helianthus annus) oil Hydrogenated C6-14 olefin polymers Isosorbide laurate
  • Hydrogenated lecithin Isostearyl neopentanoate, palmitate Hydrogenated milk lipids Isostearyl stearoyl stearate
  • Isodecyl isononanoate I. laurate Mango (Magnifera indica) oil, seed oil
  • Isodecyl neopentanoate Mango kernel oil
  • Isodecyl octanoate I. oleate Meadowfoam (Limnanthes alba) seed oil
  • Neem (Melia azadirachta) seed oil PEG-12 dioleate, P. palm kernel glycerides Neopentyl glycol dicaprate PEG- 15 cocamine oleate/phosphate
  • Oat (A vena sativa) bran extract, extract, flour PEG-20 hydrogenated castor oil triisostearate Octacosanyl stearate PEG-20 hydrogenated lanolin
  • Octyldodecyl erucate O. myristate PEG-50 hydrogenated castor oil triisostearate Octyldodecyl oleate, O. ricinoleate PEG-60 shea butter glycerides
  • Oleamine oxide PEG-75 shorea butter glycerides
  • Oleic/palmitoleic/linoleic glycerides PEG- 150
  • Palm Elaeis guineensis
  • Peanut oil Perfluoropolymethylisopropyl ether PEG-2 diisononanoate, P. dioctanoate Petrolatum
  • PEG-5 C8-12 alcohols citrate Phytantriol
  • PEG-5 C14-18 alcohols citrate Pistachio (Pistacia vera) nut oil
  • PEG-8/SMDI copolymer Polyethylene glycol Polyglyceryl-2 diisostearate, P. tetraisostearate PPG-30
  • PPG-2 lanolin alcohol ether Rapeseed Brassica campestris
  • PPG-2 myristyl ether propionate Rice Oryza sativa bran oil, bran wax
  • Tricholoma matsutake extract Capramide DEA Tridecyl behenate, T. cocoate Caprylic/capric acid
  • Tridecyl octanoate T. stearate Castor oil, ethoxylate
  • Triisostearyl trilinoleate Ceteareth-15 -17 -20 -25 Trilaurin Ceteareth-27 -29 -30 -34

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Cosmetics (AREA)

Abstract

Composition cosmétique comprenant un excipient acceptable sur le plan cosmétique qui contient un réseau polymère dont la viscosité est fonction de l'augmentation de la température comportant au moins un constituant poloxamère capable de s'agréger en réponse à un changement de température, lié de manière aléatoire à au moins un constituant acide polyacrylique, ainsi qu'un agent à activité cosmétique qui confère un effet cosmétique présélectionné, ledit excipient et ledit agent étant placés dans un milieu aqueux.
EP98922109A 1997-05-09 1998-05-08 Compositions pour applications cosmetiques Withdrawn EP1011609A4 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US85372897A 1997-05-09 1997-05-09
US853728 1997-05-09
PCT/US1998/009211 WO1998050005A1 (fr) 1997-05-09 1998-05-08 Compositions pour applications cosmetiques

Publications (2)

Publication Number Publication Date
EP1011609A1 EP1011609A1 (fr) 2000-06-28
EP1011609A4 true EP1011609A4 (fr) 2000-08-16

Family

ID=25316749

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98922109A Withdrawn EP1011609A4 (fr) 1997-05-09 1998-05-08 Compositions pour applications cosmetiques

Country Status (3)

Country Link
EP (1) EP1011609A4 (fr)
AU (1) AU7472398A (fr)
WO (1) WO1998050005A1 (fr)

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WO1998050005A1 (fr) 1998-11-12
EP1011609A1 (fr) 2000-06-28
AU7472398A (en) 1998-11-27

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