WO1997002117A1 - Shaving aid composite with an inclusion complex of a skin-soothing agent and cyclodextrin - Google Patents

Shaving aid composite with an inclusion complex of a skin-soothing agent and cyclodextrin Download PDF

Info

Publication number
WO1997002117A1
WO1997002117A1 PCT/US1996/011173 US9611173W WO9702117A1 WO 1997002117 A1 WO1997002117 A1 WO 1997002117A1 US 9611173 W US9611173 W US 9611173W WO 9702117 A1 WO9702117 A1 WO 9702117A1
Authority
WO
WIPO (PCT)
Prior art keywords
skin
cyclodextrin
shaving
water
shaving aid
Prior art date
Application number
PCT/US1996/011173
Other languages
French (fr)
Inventor
Frank E. Badin
Thilivali T. Ndou
Lee K. Lim
Yuling Yin
Mingchih Michael Tseng
Original Assignee
The Gillette Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by The Gillette Company filed Critical The Gillette Company
Priority to EP96923589A priority Critical patent/EP0837760B1/en
Priority to MX9800158A priority patent/MX9800158A/en
Priority to BR9609457A priority patent/BR9609457A/en
Priority to JP9505273A priority patent/JPH11508897A/en
Priority to DE69601542T priority patent/DE69601542T2/en
Priority to AU64062/96A priority patent/AU695164B2/en
Priority to CA002224223A priority patent/CA2224223C/en
Publication of WO1997002117A1 publication Critical patent/WO1997002117A1/en

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73Polysaccharides
    • A61K8/738Cyclodextrins
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q9/00Preparations for removing hair or for aiding hair removal
    • A61Q9/02Shaving preparations
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B26HAND CUTTING TOOLS; CUTTING; SEVERING
    • B26BHAND-HELD CUTTING TOOLS NOT OTHERWISE PROVIDED FOR
    • B26B21/00Razors of the open or knife type; Safety razors or other shaving implements of the planing type; Hair-trimming devices involving a razor-blade; Equipment therefor
    • B26B21/40Details or accessories
    • B26B21/44Means integral with, or attached to, the razor for storing shaving-cream, styptic, or the like
    • B26B21/443Lubricating strips attached to the razor head
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/24Thermal properties
    • A61K2800/244Endothermic; Cooling; Cooling sensation
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/87Application Devices; Containers; Packaging

Definitions

  • the present invention relates to a shaving system of the wet shave type, more particularly to a shaving system with an improved shaving aid composite.
  • the shaving aid composite generally comprises a water-insoluble polymer matrix, typically polystyrene, and a water-soluble shaving aid, typically polyethylene oxide, which leaches out of the composite during shaving to enhance shave comfort.
  • SUBSTTTUTE SHEET (RULE 26) aid composite.
  • a shaving aid composite i.e. lubricating strip
  • a skin-soothing agent such as an essential oil or cooling agent
  • the present invention is directed to a shaving system ofthe wet shave type comprising a blade member (one or more) and a structure which supports or holds the blade member and which has an external skin engaging portion in proximity to the blade member.
  • the shaving system may be a disposable shaving cartridge adapted for coupling to and uncoupling from a razor handle or it may be a shaving head which is integral with a razor handle so that the complete razor is discarded as a unit when the blade or blades become dulled.
  • the blade edge cooperates with the skin engaging portion to define shaving geometry.
  • the skin engaging portion includes an improved shaving aid composite which comprises an inclusion complex of a skin-soothing agent with a cyclodextrin.
  • the shaving aid composite comprises a matrix of a water-insoluble polymer and, dispersed within the matrix, a skin lubricating water-soluble polymer and an inclusion complex of a skin-soothing agent with a cyclodextrin.
  • the shaving aid composite may comprise a sheath of water-insoluble polymer that surrounds a core which includes a skin- lubricating water-soluble polymer and an inclusion complex of a skin-soothing agent with a cyclodextrin.
  • the improved shaving aid composite (or lubricating strip) is capable of retaining during normal storage conditions substantially all of the skin-soothing agent included during fabrication of the composite and delivering an effective amount of the skin-soothing agent during use.
  • Fig. 1 is a perspective view of a razor unit in accordance with the invention
  • Fig. 2 is a sectional view taken along the line 2-2 of Fig. 1; and Fig. 3 is a perspective view of another razor unit in accordance with the invention.
  • the shaving unit 10 shown in Figs. 1 and 2 includes base or platform member 12 molded of high impact polystyrene that includes integral coupling groove structure 14 for attachment to a razor handle and guard structure 16 that defines a transversely extending forward skin engaging surface 18.
  • base or platform member 12 molded of high impact polystyrene that includes integral coupling groove structure 14 for attachment to a razor handle and guard structure 16 that defines a transversely extending forward skin engaging surface 18.
  • On the upper surface of platform 12 are disposed steel leading blade 20 having a sharpened edge 22, steel following blade 24 having sharpened edge 26, and aluminum spacer member 28 that maintains blades 20 and 24 in spaced relation.
  • Cap member 30 is molded of high impact polystyrene and has body portion 32 that defines skin engaging surface 34 that extends transversely between forwardly projecting end walls 36 and has a front edge 38 that is disposed rearwardly of blade edge 26.
  • Integral rivet portions 40 extend downwardly from transversely extending body portion 32 and pass through holes in blades 20 and 24, spacer 28, and platform 12 to secure cap 30, blades 20, 24 and spacer 28 on platform 12.
  • Adhesively affixed to skin engaging surface 34 is shaving aid composite 42.
  • the shaving unit 50 shown in Fig. 3 is ofthe type shown in Jacobson, U.S. 4,586,255, and includes body 52 with front portion 54 and rear portion 56. Resiliently secured in body 52 are guard member 58, leading blade unit 60 and trailing blade unit 62.
  • a shaving aid composite in the form of elongated insert member 64 is frictionally locked in opening 66 of rear portion 56.
  • the shaving aid composite inco ⁇ orates a shaving aid which, upon contact with water, leaches out of the composite onto the skin of the user during shaving to improve the shave attributes. While shown at the rear portion of this particular shaving unit, the shaving aid composite may be located at any skin-engaging portion of the shaving unit and may be fabricated in any size or shape deemed appropriate.
  • the shaving aid composite of the present invention comprises an o inclusion complex of a skin-soothing agent, particularly a volatile skin-soothing agent, with a cyclodextrin.
  • a skin-soothing agent particularly a volatile skin-soothing agent
  • the shaving aid composite comprises a matrix of a water-insoluble polymer and, dispersed within the matrix, a skin lubricating water-soluble polymer and an inclusion complex of a skin-soothing agent with a cyclodextrin.
  • the shaving aid composite may comprise a sheath of water-insoluble polymer that surrounds a core which includes a skin-lubricating water-soluble polymer and an inclusion complex of a skin-soothing agent with a cyclodextrin, the sheath having a plurality of openings to facilitate release ofthe water-soluble polymer and skin-soothing agent.
  • the shaving aid composite may also optionally include low molecular weight water-soluble release enhancing agents such as polyethylene glycol (e.g. 1-10% by weight), water-swellable release enhancing agents such as cross-linked polyacrylics (e.g. 2-7% by weight), colorants, antioxidants, preservatives, microbiocidal agents, beard softeners, astringents, depilatories, medicinal agents, conditioning agents, etc.
  • Suitable water-insoluble polymers which can be used for the matrix (or sheath) include polyethylene, polypropylene, polystyrene, butadiene-styrene copolymer (e.g. medium and high impact polystyrene), polyacetal, acrylonitrile- butadiene-styrene copolymer, ethylene vinyl acetate copolymer and blends such as polypropylene/polystyrene blend.
  • polyethylene polypropylene
  • polystyrene polystyrene
  • butadiene-styrene copolymer e.g. medium and high impact polystyrene
  • polyacetal acrylonitrile- butadiene-styrene copolymer
  • ethylene vinyl acetate copolymer ethylene vinyl acetate copolymer
  • blends such as polypropylene/polystyrene blend.
  • the water-insoluble polymer comprises about 10 to 50%, more preferably about 15 to 40%, and most preferably about 20 to 35% by weight of the shaving aid composite.
  • the more preferred water-insoluble polymer is polystyrene, preferably a general purpose polystyrene such as Dow STYRON (Dow Chemical Company) or a high impact polystyrene (i.e. polystyrene-butadiene), such as Mobil 4324 (Mobil Co ⁇ oration).
  • the composite should contain a sufficient quantity of water-insoluble polymer to provide adequate mechanical strength, both during production and use.
  • Suitable skin lubricating water-soluble polymers include polyethylene oxide, polyvinyl pyrrolidone, polyacrylamide, hydroxypropyl cellulose, polyvinyl imidazoline, and polyhydroxyethylmethacrylate.
  • the water-soluble polymer comprises about 20 to 80%, more preferably about 40 to 75%, by weight of the shaving aid composite.
  • the more preferred water-soluble polymers are the polyethylene oxides generally known as POLYOX (available from Union Carbide Corporation) or ALKOX (available from Meisei Chemical Works, Kyoto, Japan). These polyethylene oxides will preferably have molecular weights of about 100,000 to 6 million, most preferably about 300,000 to 5 million.
  • the most preferred polyethylene oxide comprises a blend of about 40 to 80% of polyethylene oxide having an average molecular weight of about 5 million (e.g. POLYOX COAGULANT) and about 60 to 20% of polyethylene oxide having an average molecular weight of about 300,000 (e.g. POLYOX WSR-N-750).
  • the polyethylene oxide blend may also advantageously contain up to about 10% by weight of a low molecular weight (i.e. MW ⁇ 10,000) polyethylene glycol such as PEG-100.
  • the inclusion complex will generally comprise about 1% to about 25%, preferably about 5% to about 20%, most preferably about 10% to about 17%, by weight of the shaving aid composite.
  • Any suitable cyclodextrin may be utilized to form the inclusion complex including alpha-cyclodextrin, beta- cyclodextrin, gamma-cyclodextrin and modified cyclodextrins such as hydroxypropyl-beta-cyclodextrin, methyl-beta-cyclodextrin, and acetyl-beta- cyclodextrin.
  • the preferred cyclodextrins are beta-cyclodextrin and gamma- cyclodextrin.
  • Skin-soothing agents which can be used in the present invention may be any agents which have a soothing effect on the skin so as to improve shaving comfort.
  • Particularly suitable skin-soothing agents include menthol, camphor, eugenol, eucalyptol, safrol, methyl salicylate, menthyl lactate, menthyl ethoxyacetate, menthone glycerinacetal, 3-/-menthoxypropane-1,2-diol, ethyl l- menthyl carbonate, (1S,3S,4R)-p-menth-8-en-3-ol, menthyl pyrrolidone carboxylate, N-substituted-p-menthane-3-carboxamides (as described in U.S. 4,136,163, which is inco ⁇ orated herein by reference) including, for example, N-ethyl-p-menthane-3-carboxamide, acyclic carboxamides of
  • R' and R when taken separately, are each hydrogen, C C 5 alkyl or C C 8 hydroxyalkyl and provide a total of no more than 8 carbon atoms, with the proviso that when R' is hydrogen R" may also be alkylcarboxyalkyl of up to 6 carbon atoms; R' and R", when taken together, represent an alkylene group of up to 6 carbon atoms thereby forming a nitrogen heterocycle, the alkylene chain being optionally interrupted by oxygen; R 1 is hydrogen or C r C 5 alkyl; and R 2 and R 3 are each C C 5 alkyl (such acyclic carboxamides being described in U.S.
  • the cyclodextrin inclusion complexes which are utilized in the present invention may be made in the conventional manner. Typically the cyclodextrin is dissolved in an aqueous solution at or near its solubility limit at elevated temperature. The skin-soothing agent is dispersed in this solution and the insoluble complex precipitates from the solution as it is cooled. Sufficient skin- soothing agent should be added to form a 1:1, 2:1 or 3:1 molar ratio of skin- soothing agent to cyclodextrin. The amount of skin-soothing agent which can be complexed will depend on the size of the molecule and the size of the cyclodextrin cavity. After separation of the inclusion complex, it is dried in a conventional manner, typically by oven drying (e.g.
  • gamma-cyclodextrin it is also preferred to wash the complex with dry diethyl ether before drying and/or to dry it at about 116°C ovemight in order to remove all traces of water from the complex, since the presence of trace amounts of water tends to cause the skin- soothing agent to be prematurely released during fabrication ofthe shaving aid composites.
  • the shaving aid composite may additionally comprise a displacing agent which displaces the skin-soothing agent from the inclusion complex upon contact with water, thereby enhancing the release of the skin-soothing agent from the shaving aid composite during use.
  • the displacing agent will comprise about 1% to about 10%, preferably about 2% to about 7%, most preferably about 5%, by weight of the shaving aid composite.
  • Suitable displacing agents include surfactants, benzoic acids, and certain amines (e.g. urea).
  • the displacing agent is a material which is capable of forming a more stable complex with the cyclodextrin than the complex formed with the skin- soothing agent. This material will competitively displace the skin-soothing agent from the complex when the shaving aid composite is contacted with water, thus releasing the skin-soothing agent from the composite.
  • Suitable displacing agents may be readily identified by measuring the release of skin- soothing agent (e.g. menthol) from a 0.1% aqueous solution ofthe inclusion complex (e.g. ⁇ -cyclodextrin/menthol) upon addition of about 0.02% ofthe candidate displacing agent.
  • Especially preferred displacing agents include sodium lauryl sulfate, sodium dodecylbenzene sulfonate, disodium cocamido MEA sulfosuccinate (Mackanate CM-100), disodium lauryl sulfosuccinate (Mackanate LO-100), Poloxamer 188 (Pluronic F68), Poloxamer 217 (Pluronic F77), and Nonoxynol- 100 (lconol NP-100). Also preferred are benzoic acid and salicylic acid.
  • Shaving aid composites of the present invention may be fabricated by any appropriate method, including injection molding and extrusion, the latter being preferred. All of the components of the composite are blended prior to molding or extrusion. For best results, it is preferred that the inclusion complex is dry and has a particle size range of about 25 to 100 microns, most preferably about 40 to 75 microns. The particle size can be controlled by screening using known methods. Drying can be performed in a vacuum or convection oven at about 90-120°C for about 3 to 15 hours. The blended components may be extruded through a Haake System 90
  • 3/4 inch diameter extruder with a barrel pressure of about 1000-2000 psi, a rotor speed of about 10 to 50 ⁇ m, and a temperature of about 150-185°C and a die temperature of about 170-185°C.
  • a 1 1 / 4 inch single screw extruder may be employed with a processing temperature of 175-200°C, preferably 185-190°C, a screw speed of 20 to 50 ⁇ m, preferably 25 to 35 rpm, and an extrusion pressure of 1800 to 5000 psi, preferably 2000 to 3500 psi.
  • the extruded strip is air cooled to about 25°C.
  • the strips it is preferred to first extrude the powder blend into pellets. This can be done on a 1 4 or 1 2 inch single screw extruder at a temperature of 120-180°C, preferably 140-150°C, with a screw speed of 20 to 100 ⁇ m, preferably 45 to 70 ⁇ m.
  • the pellets are then molded in either a single material molding or multi-material molding machine, which may be single cavity or multi-cavity, optionally equipped with a hotrunner system.
  • the process temperature can be from 165 to 250°C, preferably from 180 to 225°C.
  • the injection pressure should be sufficient to fill the part completely without flashing. Depending on the cavity size, configuration and quantity, the injection pressure can range from 300 to 2500 psi.
  • the cycle time is dependent on the same parameters and can range from 3 to 30 seconds, with the optimum generally being about 6 to 15 seconds.
  • the invention may be further illustrated by the following examples in which all parts and percentages are by weight.
  • ⁇ -CD/M Preparation of ⁇ -CD/M.
  • a 10% aqueous solution of beta-cyclodextrin is prepared and maintained at 40-45°C with stirring.
  • Sufficient menthol is added to provide a 1 :1 molar ratio of cyclodextrin to menthol.
  • the solution is allowed to cool to room temperature while maintaining continuous stirring.
  • the precipitate is collected and dried ovemight in a vacuum oven at 110°C.
  • HP- ⁇ -CD/M Preparation of HP- ⁇ -CD/M.
  • a 75% aqueous slurry of hydroxypropyl- beta-cyclodextrin is prepared and maintained at 40-45°C with stirring.
  • Sufficient menthol is added to provide a 1 :1 molar ratio of cyclodextrin to menthol.
  • the solution is allowed to cool to room temperature while maintaining continuous stirring.
  • the precipitate is collected by filtration and dried overnight in a vacuum oven at 110°C.
  • ⁇ -CD/M Preparation of ⁇ -CD/M.
  • Three 20% aqueous solutions of gamma- cyclodextrin are prepared and maintained at 40-45°C with stirring.
  • Sufficient menthol is added to each solution to provide a 1 :1 , 1 :2 or 1 :3 molar ratio of cyclodextrin to menthol respectively.
  • the solutions are allowed to cool to room temperature while maintaining continuous stirring.
  • the precipitates are collected, dried ovemight in a vacuum oven at 110°C, washed with dry diethyl ether and, after removal of the ether by water aspiration, dried in a hood.
  • the collected complexes are dried in a vacuum oven at 110°C overnight.
  • the recovered complexes contain about 10%, about 17% and about 19% menthol respectively.
  • Example 4 Preparation of ⁇ -CD/menthyl lactate.
  • a 10% aqueous solution of beta- cyclodextrin is prepared and maintained at 40-45°C with stirring.
  • Sufficient menthyl lactate is added to provide a 1 :1 molar ratio of cyclodextrin to menthyl lactate.
  • the solution is allowed to cool to room temperature while maintaining continuous stirring.
  • the precipitate is collected and dried ovemight in a vacuum oven at 110°C.
  • Shaving aid composites similar to insert member 64 shown in Fig. 3 are fabricated from the blends indicated below by extruding the blends through a Haake System 90 3/4 inch diameter extruder with a barrel pressure of about 1000-2000 psi, a rotor speed of about 10 to 50 rpm, and a temperature of about 150-185°C and a die temperature of about 170-185°C.
  • the extruded strip of composite is cooled and sliced to appropriate lengths for securing into openings 66 of shaving units 50.
  • the polystyrene is Dow STYRON or Mobil 2824
  • the high impact polystyrene (“Hips") is Mobil 4324
  • the polyethylene oxide 60/40
  • Blend N Blend O
  • each of the foregoing strips retains a substantial portion (i.e. >50%) of the skin-soothing agent (i.e. menthol or menthol analog) included during fabrication when stored at 45°C for four days.
  • each of the foregoing strips releases skin-soothing agent when contacted with water.

Abstract

The present invention is directed to a shaving system of the wet shave type comprising a blade member (one or more) (20, 24) and a structure (12) which supports or holds the blade member and which has an external skin engaging portion (34) in proximity to the blade member. The skin engaging portion (34) includes an improved shaving aid composite (42) (or lubricating strip) which contains an inclusion complex of a skin-soothing agent, such as menthol, with a cyclodextrin. Preferably the shaving aid composite (42) comprises a matrix of a water-insoluble polymer, an effective amount of a skin lubricating water-soluble polymer dispersed within the matrix, and an inclusion complex of a skin-soothing agent with a cyclodextrin. Alternatively, the shaving aid composite (42) may comprise a sheath of water-insoluble polymer that surrounds a core which includes a skin-lubricating water-soluble polymer and an inclusion complex of a skin-soothing agent with a cyclodextrin. The improved shaving aid composite (42) is capable of retaining during normal storage conditions substantially all of the skin-soothing agent included during fabrication of the composite and delivering an effective amount of the skin-soothing agent during use.

Description

SHAVING AID COMPOSITE WITH AN INCLUSION COMPLEX OF A SKIN-SOOTHING AGENT AND CYCLODEXTRIN
The present invention relates to a shaving system of the wet shave type, more particularly to a shaving system with an improved shaving aid composite.
It is now well known that shaving comfort can be enhanced by affixing to a razor cartridge a shaving aid composite, also known as a lubricating strip, which continuously releases a shaving aid, typically a lubricant, during the shaving process. See, for example, U.S. 4,1 70,821 and GB 2,024,082. The shaving aid composite generally comprises a water-insoluble polymer matrix, typically polystyrene, and a water-soluble shaving aid, typically polyethylene oxide, which leaches out of the composite during shaving to enhance shave comfort.
Unfortunately, conventional shaving aid composites suffer from the disadvantage that they release an insufficient amount of the shaving aid, particularly after the first three or four shaves where release of the shaving aid may drop off to negligible quantities. Accordingly, recent efforts have been made to improve shaving aid composites so as to enhance and prolong release of the shaving aid. Such efforts have resulted in improved shaving aid composites which include the following: incorporation of low molecular weight release enhancing agent, such as polyethylene glycol, into the matrix, disclosed in U.S. 5,1 13,585; the use of ethylene vinyl acetate copolymer as the matrix material, disclosed in U.S. 5,349,750; incorporation of a water- swellable polymer such as Salsorb 84, a cross-linked polyacrylic, disclosed in WO 95/07803; incorporation of a compatibilizer material such as polyethylene oxide-polypropylene oxide copolymer (e.g. Poloxamer 1 82), disclosed in U.S. 5,454,1 64; and co-extrusion of a core comprising a water-leachable shaving aid within a sheath of water- insoluble polymer, wherein the sheath has a plurality of openings to facilitate release of the shaving aid, disclosed in WO 96/1 3360. All of the aforementioned patents or patent applications are incorporated herein by reference.
It has also been suggested in U.S. 5,095,61 9 that a water-insoluble essential oil, such as menthol, may be advantageously included in a shaving
SUBSTTTUTE SHEET (RULE 26) aid composite. However, it has been found in practice that a substantial amount of the essential oil is lost due to volatilization prior to use, rendering the composite unable to deliver an effective amount of the essential oil. It is an object of the present invention to provide a shaving aid composite (i.e. lubricating strip) which is capable of retaining during normal storage conditions substantially all of a skin-soothing agent, such as an essential oil or cooling agent, included during fabrication of the composite and delivering an effective amount of the skin-soothing agent during use.
The present invention is directed to a shaving system ofthe wet shave type comprising a blade member (one or more) and a structure which supports or holds the blade member and which has an external skin engaging portion in proximity to the blade member. The shaving system may be a disposable shaving cartridge adapted for coupling to and uncoupling from a razor handle or it may be a shaving head which is integral with a razor handle so that the complete razor is discarded as a unit when the blade or blades become dulled. The blade edge cooperates with the skin engaging portion to define shaving geometry.
The skin engaging portion includes an improved shaving aid composite which comprises an inclusion complex of a skin-soothing agent with a cyclodextrin. Preferably the shaving aid composite comprises a matrix of a water-insoluble polymer and, dispersed within the matrix, a skin lubricating water-soluble polymer and an inclusion complex of a skin-soothing agent with a cyclodextrin. Alternatively, the shaving aid composite may comprise a sheath of water-insoluble polymer that surrounds a core which includes a skin- lubricating water-soluble polymer and an inclusion complex of a skin-soothing agent with a cyclodextrin. The improved shaving aid composite (or lubricating strip) is capable of retaining during normal storage conditions substantially all of the skin-soothing agent included during fabrication of the composite and delivering an effective amount of the skin-soothing agent during use.
Fig. 1 is a perspective view of a razor unit in accordance with the invention;
Fig. 2 is a sectional view taken along the line 2-2 of Fig. 1; and Fig. 3 is a perspective view of another razor unit in accordance with the invention.
The shaving unit 10 shown in Figs. 1 and 2 includes base or platform member 12 molded of high impact polystyrene that includes integral coupling groove structure 14 for attachment to a razor handle and guard structure 16 that defines a transversely extending forward skin engaging surface 18. On the upper surface of platform 12 are disposed steel leading blade 20 having a sharpened edge 22, steel following blade 24 having sharpened edge 26, and aluminum spacer member 28 that maintains blades 20 and 24 in spaced relation. Cap member 30 is molded of high impact polystyrene and has body portion 32 that defines skin engaging surface 34 that extends transversely between forwardly projecting end walls 36 and has a front edge 38 that is disposed rearwardly of blade edge 26. Integral rivet portions 40 extend downwardly from transversely extending body portion 32 and pass through holes in blades 20 and 24, spacer 28, and platform 12 to secure cap 30, blades 20, 24 and spacer 28 on platform 12. Adhesively affixed to skin engaging surface 34 is shaving aid composite 42.
The shaving unit 50 shown in Fig. 3 is ofthe type shown in Jacobson, U.S. 4,586,255, and includes body 52 with front portion 54 and rear portion 56. Resiliently secured in body 52 are guard member 58, leading blade unit 60 and trailing blade unit 62. A shaving aid composite in the form of elongated insert member 64 is frictionally locked in opening 66 of rear portion 56. The shaving aid composite incoφorates a shaving aid which, upon contact with water, leaches out of the composite onto the skin of the user during shaving to improve the shave attributes. While shown at the rear portion of this particular shaving unit, the shaving aid composite may be located at any skin-engaging portion of the shaving unit and may be fabricated in any size or shape deemed appropriate.
The shaving aid composite of the present invention comprises an o inclusion complex of a skin-soothing agent, particularly a volatile skin-soothing agent, with a cyclodextrin. Preferably the shaving aid composite comprises a matrix of a water-insoluble polymer and, dispersed within the matrix, a skin lubricating water-soluble polymer and an inclusion complex of a skin-soothing agent with a cyclodextrin. Altematively, the shaving aid composite may comprise a sheath of water-insoluble polymer that surrounds a core which includes a skin-lubricating water-soluble polymer and an inclusion complex of a skin-soothing agent with a cyclodextrin, the sheath having a plurality of openings to facilitate release ofthe water-soluble polymer and skin-soothing agent. The shaving aid composite may also optionally include low molecular weight water-soluble release enhancing agents such as polyethylene glycol (e.g. 1-10% by weight), water-swellable release enhancing agents such as cross-linked polyacrylics (e.g. 2-7% by weight), colorants, antioxidants, preservatives, microbiocidal agents, beard softeners, astringents, depilatories, medicinal agents, conditioning agents, etc.
Suitable water-insoluble polymers which can be used for the matrix (or sheath) include polyethylene, polypropylene, polystyrene, butadiene-styrene copolymer (e.g. medium and high impact polystyrene), polyacetal, acrylonitrile- butadiene-styrene copolymer, ethylene vinyl acetate copolymer and blends such as polypropylene/polystyrene blend.
Preferably the water-insoluble polymer comprises about 10 to 50%, more preferably about 15 to 40%, and most preferably about 20 to 35% by weight of the shaving aid composite. The more preferred water-insoluble polymer is polystyrene, preferably a general purpose polystyrene such as Dow STYRON (Dow Chemical Company) or a high impact polystyrene (i.e. polystyrene-butadiene), such as Mobil 4324 (Mobil Coφoration). The composite should contain a sufficient quantity of water-insoluble polymer to provide adequate mechanical strength, both during production and use.
Suitable skin lubricating water-soluble polymers include polyethylene oxide, polyvinyl pyrrolidone, polyacrylamide, hydroxypropyl cellulose, polyvinyl imidazoline, and polyhydroxyethylmethacrylate. Preferably the water-soluble polymer comprises about 20 to 80%, more preferably about 40 to 75%, by weight of the shaving aid composite.
The more preferred water-soluble polymers are the polyethylene oxides generally known as POLYOX (available from Union Carbide Corporation) or ALKOX (available from Meisei Chemical Works, Kyoto, Japan). These polyethylene oxides will preferably have molecular weights of about 100,000 to 6 million, most preferably about 300,000 to 5 million. The most preferred polyethylene oxide comprises a blend of about 40 to 80% of polyethylene oxide having an average molecular weight of about 5 million (e.g. POLYOX COAGULANT) and about 60 to 20% of polyethylene oxide having an average molecular weight of about 300,000 (e.g. POLYOX WSR-N-750). The polyethylene oxide blend may also advantageously contain up to about 10% by weight of a low molecular weight (i.e. MW<10,000) polyethylene glycol such as PEG-100.
The inclusion complex will generally comprise about 1% to about 25%, preferably about 5% to about 20%, most preferably about 10% to about 17%, by weight of the shaving aid composite. Any suitable cyclodextrin may be utilized to form the inclusion complex including alpha-cyclodextrin, beta- cyclodextrin, gamma-cyclodextrin and modified cyclodextrins such as hydroxypropyl-beta-cyclodextrin, methyl-beta-cyclodextrin, and acetyl-beta- cyclodextrin. The preferred cyclodextrins are beta-cyclodextrin and gamma- cyclodextrin.
Skin-soothing agents which can be used in the present invention may be any agents which have a soothing effect on the skin so as to improve shaving comfort. Particularly suitable skin-soothing agents include menthol, camphor, eugenol, eucalyptol, safrol, methyl salicylate, menthyl lactate, menthyl ethoxyacetate, menthone glycerinacetal, 3-/-menthoxypropane-1,2-diol, ethyl l- menthyl carbonate, (1S,3S,4R)-p-menth-8-en-3-ol, menthyl pyrrolidone carboxylate, N-substituted-p-menthane-3-carboxamides (as described in U.S. 4,136,163, which is incoφorated herein by reference) including, for example, N-ethyl-p-menthane-3-carboxamide, acyclic carboxamides of the formula
R1
I R2- C*-CONR ' R"
I R3 where R' and R", when taken separately, are each hydrogen, C C5 alkyl or C C8 hydroxyalkyl and provide a total of no more than 8 carbon atoms, with the proviso that when R' is hydrogen R" may also be alkylcarboxyalkyl of up to 6 carbon atoms; R' and R", when taken together, represent an alkylene group of up to 6 carbon atoms thereby forming a nitrogen heterocycle, the alkylene chain being optionally interrupted by oxygen; R1 is hydrogen or CrC5 alkyl; and R2 and R3 are each C C5 alkyl (such acyclic carboxamides being described in U.S. 4,153,679, which is incorporated herein by reference) including, for example, N,2,3-trimethyl-2-isopropylbutanamide, and ketal coolants (as described in WO 93/23005, which is incorporated herein by reference) including, for example, /-menthon-/-/-isomenthon glycerin ketal.
The cyclodextrin inclusion complexes which are utilized in the present invention may be made in the conventional manner. Typically the cyclodextrin is dissolved in an aqueous solution at or near its solubility limit at elevated temperature. The skin-soothing agent is dispersed in this solution and the insoluble complex precipitates from the solution as it is cooled. Sufficient skin- soothing agent should be added to form a 1:1, 2:1 or 3:1 molar ratio of skin- soothing agent to cyclodextrin. The amount of skin-soothing agent which can be complexed will depend on the size of the molecule and the size of the cyclodextrin cavity. After separation of the inclusion complex, it is dried in a conventional manner, typically by oven drying (e.g. at about 100-110°C) optionally under vacuum. When gamma-cyclodextrin is utilized, it is also preferred to wash the complex with dry diethyl ether before drying and/or to dry it at about 116°C ovemight in order to remove all traces of water from the complex, since the presence of trace amounts of water tends to cause the skin- soothing agent to be prematurely released during fabrication ofthe shaving aid composites.
The shaving aid composite may additionally comprise a displacing agent which displaces the skin-soothing agent from the inclusion complex upon contact with water, thereby enhancing the release of the skin-soothing agent from the shaving aid composite during use. The displacing agent will comprise about 1% to about 10%, preferably about 2% to about 7%, most preferably about 5%, by weight of the shaving aid composite. Suitable displacing agents include surfactants, benzoic acids, and certain amines (e.g. urea).
The displacing agent is a material which is capable of forming a more stable complex with the cyclodextrin than the complex formed with the skin- soothing agent. This material will competitively displace the skin-soothing agent from the complex when the shaving aid composite is contacted with water, thus releasing the skin-soothing agent from the composite. Suitable displacing agents may be readily identified by measuring the release of skin- soothing agent (e.g. menthol) from a 0.1% aqueous solution ofthe inclusion complex (e.g. β-cyclodextrin/menthol) upon addition of about 0.02% ofthe candidate displacing agent. In this procedure the solution is evaporated in a Savant SpeedVac Concentrator (Model RT-490A), leaving a cycodextrin residue which is extracted with methanol. The methanol extract is analyzed for non-released skin-soothing agent by gas chromatography.
The following Table illustrates the displacement potential of various candidate displacing agents.
Displacement Of Menthol From 0.1% β-CD/M Complex In Water
Displacing Agent Menthol Released
Sodium lauryl sulfate 100%
Sodium dodecyl benzene sulfonate 100%
Disodium lauryl sulfosuccinate 48%
Disodium cocamido MEA sulfosuccinate 47%
Sodium diamyl sulfosuccinate 38%
Cetylpyridinium chloride 52%
Cetyldimethylethylammonium bromide 50%
Benzalkonium chloride 44%
Benzethonium chloride 43%
Poloxamer 188 45%
Poloxamer 217 45%
Nonoxynol-100 42%
Poloxamer 407 39%
Poloxamer 238 38%
Laureth-23 36%
Oleth-20 36%
Benzoic acid 46%
Salicylic acid 43%
Urea 61%
Control (β-CD/M only; no displacing agent) 27%
Especially preferred displacing agents include sodium lauryl sulfate, sodium dodecylbenzene sulfonate, disodium cocamido MEA sulfosuccinate (Mackanate CM-100), disodium lauryl sulfosuccinate (Mackanate LO-100), Poloxamer 188 (Pluronic F68), Poloxamer 217 (Pluronic F77), and Nonoxynol- 100 (lconol NP-100). Also preferred are benzoic acid and salicylic acid.
Shaving aid composites of the present invention may be fabricated by any appropriate method, including injection molding and extrusion, the latter being preferred. All of the components of the composite are blended prior to molding or extrusion. For best results, it is preferred that the inclusion complex is dry and has a particle size range of about 25 to 100 microns, most preferably about 40 to 75 microns. The particle size can be controlled by screening using known methods. Drying can be performed in a vacuum or convection oven at about 90-120°C for about 3 to 15 hours. The blended components may be extruded through a Haake System 90
3/4 inch diameter extruder with a barrel pressure of about 1000-2000 psi, a rotor speed of about 10 to 50 φm, and a temperature of about 150-185°C and a die temperature of about 170-185°C. Alternatively, a 11/4 inch single screw extruder may be employed with a processing temperature of 175-200°C, preferably 185-190°C, a screw speed of 20 to 50 φm, preferably 25 to 35 rpm, and an extrusion pressure of 1800 to 5000 psi, preferably 2000 to 3500 psi. The extruded strip is air cooled to about 25°C.
To injection mold the strips it is preferred to first extrude the powder blend into pellets. This can be done on a 1 4 or 1 2 inch single screw extruder at a temperature of 120-180°C, preferably 140-150°C, with a screw speed of 20 to 100 φm, preferably 45 to 70 φm. The pellets are then molded in either a single material molding or multi-material molding machine, which may be single cavity or multi-cavity, optionally equipped with a hotrunner system. The process temperature can be from 165 to 250°C, preferably from 180 to 225°C. The injection pressure should be sufficient to fill the part completely without flashing. Depending on the cavity size, configuration and quantity, the injection pressure can range from 300 to 2500 psi. The cycle time is dependent on the same parameters and can range from 3 to 30 seconds, with the optimum generally being about 6 to 15 seconds. The invention may be further illustrated by the following examples in which all parts and percentages are by weight.
Example 1
Preparation of β-CD/M. A 10% aqueous solution of beta-cyclodextrin is prepared and maintained at 40-45°C with stirring. Sufficient menthol is added to provide a 1 :1 molar ratio of cyclodextrin to menthol. After mixing for about three hours, the solution is allowed to cool to room temperature while maintaining continuous stirring. The precipitate is collected and dried ovemight in a vacuum oven at 110°C. Example 2
Preparation of HP-β-CD/M. A 75% aqueous slurry of hydroxypropyl- beta-cyclodextrin is prepared and maintained at 40-45°C with stirring. Sufficient menthol is added to provide a 1 :1 molar ratio of cyclodextrin to menthol. After mixing for about one hour, the solution is allowed to cool to room temperature while maintaining continuous stirring. The precipitate is collected by filtration and dried overnight in a vacuum oven at 110°C.
Example 3
Preparation of γ-CD/M. Three 20% aqueous solutions of gamma- cyclodextrin are prepared and maintained at 40-45°C with stirring. Sufficient menthol is added to each solution to provide a 1 :1 , 1 :2 or 1 :3 molar ratio of cyclodextrin to menthol respectively. After mixing for about three hours, the solutions are allowed to cool to room temperature while maintaining continuous stirring. The precipitates are collected, dried ovemight in a vacuum oven at 110°C, washed with dry diethyl ether and, after removal of the ether by water aspiration, dried in a hood. Alternatively, the collected complexes are dried in a vacuum oven at 110°C overnight. The recovered complexes contain about 10%, about 17% and about 19% menthol respectively.
Example 4 Preparation of β-CD/menthyl lactate. A 10% aqueous solution of beta- cyclodextrin is prepared and maintained at 40-45°C with stirring. Sufficient menthyl lactate is added to provide a 1 :1 molar ratio of cyclodextrin to menthyl lactate. After mixing for about three hours, the solution is allowed to cool to room temperature while maintaining continuous stirring. The precipitate is collected and dried ovemight in a vacuum oven at 110°C.
Example 5
Shaving aid composites similar to insert member 64 shown in Fig. 3 are fabricated from the blends indicated below by extruding the blends through a Haake System 90 3/4 inch diameter extruder with a barrel pressure of about 1000-2000 psi, a rotor speed of about 10 to 50 rpm, and a temperature of about 150-185°C and a die temperature of about 170-185°C.The extruded strip of composite is cooled and sliced to appropriate lengths for securing into openings 66 of shaving units 50. In the blends listed below, the polystyrene is Dow STYRON or Mobil 2824, the high impact polystyrene ("Hips") is Mobil 4324, the polyethylene oxide (60/40) is a blend of 60% POLYOX COAGULANT (M.W. 5 million) and 40% POLYOX WSR-N-750 (M.W. 300,000), and the polyethylene glycol ("PEG") is Dow 4500 PEG (MW=4500).
Blend A Blend B
28.5% Hips 26.8% Hips
46.8% polyethylene oxide 44.0% polyethylene oxide
8.5% PEG 8.0% PEG 15.0% β-CD/M 15.0% β-CD/M
1.2% colorant/antioxidant 5.0% disodium cocamido MEA sulfosuccinate 1.2% colorant/antioxidant
Blend C Blend D 26.8% Hips 26.8% Hips
44.0% polyethylene oxide 44.0% polyethylene oxide 8.0% PEG 8.0% PEG 15.0% β-CD/M 15.0% β-CD/M 5.0% Poloxamer 188 5.0% sodium dodecylbenzenesulfonate 1.2% colorant/antioxidant 1.2% colorant/antioxidant
Blends E. F. &G Blend H
28.5% Hips 28.5% Hips
46.7% polyethylene oxide 46.7% polyethylene oxide
8.5% PEG 8.5% PEG 15.0% γ-CD/M (1 :1 , 1:2 & 1 :3 resp.) 15.0% HP-β-CD/M
1.2% colorant/antioxidant 1.2% colorant/antioxidant Blend J Blend K
23.8% polystyrene 26.8% Hips 54.8% polyethylene oxide 44.0% polyethylene oxide
5.0% Salsorb 88 8.0% PEG 15.0% γ-CD/M (11.4% menthol) 15.0% β-CD/M
1.4% colorant/antioxidant 5.0% salicylic acid
1.2% colorant/antioxidant
Blend L Blend M
27.8% Hips 33.5% Hips
45.7% polyethylene oxide 37.3% polyethylene oxide
8.3% PEG 8.0% PEG 15.0% β-CD/M 15.0% β-CD/M
2.0% Na dodecylbenzenesulfonate 5.0% disodium cocamido MEA sulfosuccinate
1.2% colorant/antioxidant 1.2% colorant/antioxidant
Blend N Blend O
26.8% Hips 23.8% polystyrene 44.0% polyethylene oxide 49.8% polyethylene oxide
8.0% PEG 5.0% Salsorb 88
15.0% β-CD/menthyl lactate 20.0% γ-CD/M (1 :2) 5.0% Nonoxynol-100 1.4% colorant/antioxidant 1.2% colorant/antioxidant
Blend P
23.8% polystyrene 59.8% polyethylene oxide 15.0% γ-CD/M (11.4% menthol) 1.4% colorant/antioxidant
Each of the foregoing strips retains a substantial portion (i.e. >50%) of the skin-soothing agent (i.e. menthol or menthol analog) included during fabrication when stored at 45°C for four days. In addition, each of the foregoing strips releases skin-soothing agent when contacted with water.

Claims

C L A I S
1. A shaving system of the wet shave type comprising a blade member and structure defining an external skin engaging portion in proximity to said blade member, said skin engaging portion including a shaving aid composite comprising an inclusion complex of a skin-soothing agent with a cyclodextrin.
2. The shaving system according to claim 1 wherein the shaving aid composite comprises a water-insoluble polymer, a skin lubricating water-soluble polymer, and an inclusion complex of a skin-soothing agent with a cyclodextrin.
3. The shaving system according to claim 1 wherein the shaving aid composite comprises a matrix of a water-insoluble polymer and, dispersed within the matrix, a skin lubricating water-soluble polymer and an inclusion complex of a skin-soothing agent with a cyclodextrin.
4. The shaving system according to any preceding claim wherein the cyclodextrin is selected from alpha-cyclodextrin, beta-cyclodextrin, gamma- cyclodextrin and hydroxypropyl-beta-cyclodextrin, methy l-beta-cyclodextrin, and acety l-beta-cyclodextrin.
5. The shaving system according to any preceding claim wherein the skin- soothing agent is selected from the group consisting of menthol, camphor, eugenol, eucalyptol, safrol, methyl salicylate, menthyl lactate, menthyl ethoxyacetate, menthone glycerinacetal, 3-/-menthoxypropane-1,2-diol, ethyl /- menthyl carbonate, (1S,3S,4R)-p-menth-8-en-3-ol, menthyl pyrrolidone carboxylate, N-ethyl-p-menthane-3-carboxamide, N,2,3-trimethyl-2-isopropyl- butanamide, and /-menthon-Λi-isomenthon glycerin ketal.
6. The shaving system according to any preceding claim wherein the shaving aid composite additionally comprises a displacing agent which displaces the skin- soothing agent from the inclusion complex upon contact with water, thereby enhancing the release ofthe skin-soothing agent from the shaving aid composite during use.
7. The shaving system according to claim 6 wherein the displacing agent is a surfactant.
8. The shaving system according to claim 7 wherein the surfactant is selected from sodium lauryl sulfate, sodium dodecylbenzene sulfonate, disodium cocamido MEA sulfosuccinate, disodium lauryl sulfosuccinate, Poloxamer 188, Poloxamer 217 and Nonoxynol-100.
9. The shaving system according to claim 6 wherein the displacing agent is benzoic acid or salicylic acid.
10. The shaving system according to any preceding claim wherein the cyclodextrin is beta-cyclodextrin.
11. The shaving system according to any preceding claim wherein the shaving aid composite comprises about 15% to about 40% by weight of the water- insoluble polymer, about 20% to about 80% by weight of the water-soluble polymer, and about 1% to about 25% by weight of the inclusion complex.
12. The shaving system according to any preceding claim wherein the water- insoluble polymer is selected from the group consisting of polyethylene, polypropylene, polystyrene, polystyrene-butadiene copolymer, polyacetal, acrylonitrile-butadiene-styrene copolymer, and ethylene vinyl acetate copolymer and the water-soluble polymer is selected from the group consisting of polyethylene oxide, polyvinyl pyrrolidone, polyacrylamide, hydroxypropyl cellulose, polyvinyl imidazoline, and polyhydroxyethylmethacrylate.
13. The shaving system according to any preceding claim wherein the shaving aid composite comprises about 1% to about 10% by weight of said displacing agent.
14. The shaving system according to any preceding claim wherein the shaving aid composite comprises about 20% to about 35% by weight polystyrene or polystyrene-butadiene, about 40% to about 75% by weight polyethylene oxide and about 5% to about 20% by weight inclusion complex.
15. The shaving system according to any preceding claim wherein the water- soluble polymer comprises a blend of polyethylene oxide having an average molecular weight of about 5 million and a polyethylene oxide having an average molecular weight of about 300,000.
16. The shaving system according to any preceding claim wherein the shaving aid composite additionally comprises polyethylene glycol and/or a water-swellable polymer.
PCT/US1996/011173 1995-06-30 1996-06-28 Shaving aid composite with an inclusion complex of a skin-soothing agent and cyclodextrin WO1997002117A1 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
EP96923589A EP0837760B1 (en) 1995-06-30 1996-06-28 Wet shavingsystem with shaving aid composite with an inclusion complex of a skin-soothing agent and cyclodextrin
MX9800158A MX9800158A (en) 1995-06-30 1996-06-28 Shaving aid composite with an inclusion complex of a skin-soothing agent and cyclodextrin.
BR9609457A BR9609457A (en) 1995-06-30 1996-06-28 Wet shave type shaving system
JP9505273A JPH11508897A (en) 1995-06-30 1996-06-28 Shaving aid composite comprising an emollient and an inclusion complex of cyclodextrin
DE69601542T DE69601542T2 (en) 1995-06-30 1996-06-28 WAVE SHAVER WITH A SHAVING AID COMPOSITE WITH AN INCLUSIVE COMPLEX OF A SKIN DETERGENT AND CYCLODEXTRINE
AU64062/96A AU695164B2 (en) 1995-06-30 1996-06-28 Shaving aid composite with an inclusion complex of a skin-soothing agent and cyclodextrin
CA002224223A CA2224223C (en) 1995-06-30 1996-06-28 Shaving aid composite with an inclusion complex of a skin-soothing agent and cyclodextrin

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US08/496,860 US5653971A (en) 1995-06-30 1995-06-30 Shaving aid composite with an inclusion complex of a skin-soothing agent and a cyclodextrin
US08/496,860 1995-06-30

Publications (1)

Publication Number Publication Date
WO1997002117A1 true WO1997002117A1 (en) 1997-01-23

Family

ID=23974488

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1996/011173 WO1997002117A1 (en) 1995-06-30 1996-06-28 Shaving aid composite with an inclusion complex of a skin-soothing agent and cyclodextrin

Country Status (14)

Country Link
US (1) US5653971A (en)
EP (1) EP0837760B1 (en)
JP (1) JPH11508897A (en)
AR (1) AR002635A1 (en)
AT (1) ATE176616T1 (en)
AU (1) AU695164B2 (en)
BR (1) BR9609457A (en)
CA (1) CA2224223C (en)
CO (1) CO4750633A1 (en)
DE (1) DE69601542T2 (en)
ES (1) ES2129980T3 (en)
MX (1) MX9800158A (en)
WO (1) WO1997002117A1 (en)
ZA (1) ZA965481B (en)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0827735A1 (en) 1996-09-04 1998-03-11 Warner-Lambert Company Shaving aid with physiological cooling effect
EP0835649A1 (en) * 1996-09-04 1998-04-15 Warner-Lambert Company Shaving aid with complexing agent
US7727516B2 (en) 2006-02-28 2010-06-01 The Procter & Gamble Company Reduction of hair growth
EP2286787A2 (en) 2009-08-21 2011-02-23 The Gillette Company Hair removal device
EP2286788A2 (en) 2009-08-21 2011-02-23 The Gillette Company Hair removal device
WO2011103235A2 (en) 2010-02-18 2011-08-25 The Gillette Company Hair removal device comprising an erodable composition
WO2011102996A2 (en) 2010-02-18 2011-08-25 The Gillette Company Hair removal device comprising erodable moisturizer
WO2011103072A1 (en) 2010-02-18 2011-08-25 The Gillette Company Hair removal device comprising moisturizing compositions
EP2517693A1 (en) 2011-04-26 2012-10-31 The Gillette Company Hair removal device comprising a modifying surfactant
EP2537511A1 (en) 2011-06-24 2012-12-26 The Gillette Company Hair removal device comprising erodable moisturizer
EP2591895A1 (en) 2011-11-10 2013-05-15 The Gillette Company Razor cartridge with lubrication and moisturizing strips
WO2015148308A1 (en) * 2014-03-26 2015-10-01 The Gillette Company Skin engaging shavng aid comprising a thermally resilient sensate and a trpa1 receptor inhibitor

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6295733B1 (en) 1994-08-03 2001-10-02 Warner-Lambert Company Changeable color shaving aid
US6167625B1 (en) 1999-05-18 2001-01-02 Warner-Lambert Company Shaving implement
US6532667B1 (en) 2000-07-28 2003-03-18 Emory L. Leaseburge Replaceable lubricating device for a razor
WO2004043654A2 (en) * 2002-11-06 2004-05-27 Eveready Battery Company, Inc. Shaving systems
US20050015990A1 (en) * 2003-07-25 2005-01-27 Barone Chris A. Method for producing a shaving aid cartridge
GB2450169B (en) * 2007-06-15 2011-06-29 Lrc Products Personal lubricant composition
US9044429B2 (en) * 2010-01-15 2015-06-02 The Gillette Company Personal care compositions comprising a methyl naphthalenyl ketone or a derivative thereof
US20120087981A1 (en) * 2010-10-11 2012-04-12 Xiandong Wang Skin Engaging Member Comprising Encapsulated Actives
US20120093897A1 (en) 2010-10-15 2012-04-19 Alison Fiona Stephens Skin Engaging Member Comprising An Emollient
US20120090179A1 (en) 2010-10-15 2012-04-19 Alison Fiona Stephens Skin Engaging Member Forming A Ring
EP2627487A1 (en) 2010-10-15 2013-08-21 The Gillette Company A method of making a skin engaging member
CN102115572B (en) * 2010-12-27 2012-12-19 宁波大学 Lubricating strip for shaver and shaver provided with same
US20130042482A1 (en) 2011-08-16 2013-02-21 Valerie Jean Bradford Skin Engaging Member Comprising An Anti-Irritation Agent
AU2013323690B2 (en) 2012-09-28 2016-09-22 The Gillette Company Llc A skin engaging member comprising at least one thermally resilient sensate
BR112015006847B1 (en) 2012-09-28 2020-02-04 Gillette Co an auxiliary element for shaving or epilating skin contact comprising at least one thermally resilient sensitizing substance
CN105163810A (en) * 2013-04-24 2015-12-16 吉列公司 Lubricating shaving aid member
US20140322153A1 (en) * 2013-04-24 2014-10-30 The Gillette Company Lubricating Skin Engaging Member
US9216514B2 (en) * 2013-11-01 2015-12-22 The Gillette Company Manually actuatable liquid dispensing razor
US9321182B2 (en) * 2013-11-01 2016-04-26 The Gillette Company Razor cartridge for a liquid dispensing razor
US20150164778A1 (en) * 2013-12-18 2015-06-18 Honorio OBIAS Pre-mix and process for preparing personal care compositions, composition promoting improved and long-lasting cleansing sensory experience, improved oral care composition
US20150273711A1 (en) 2014-03-26 2015-10-01 The Gillette Company Razor Comprising A Molded Shaving Aid Composition Comprising A Thermally Resilient Sensate
US20150307447A1 (en) 2014-04-23 2015-10-29 The Procter & Gamble Company Compositions for deposition on biological surfaces
SG11201703353RA (en) 2014-11-26 2017-06-29 Gillette Co Llc A skin engaging member comprising ethylene vinyl acetate
MX2017008209A (en) * 2014-12-18 2017-10-06 Gillette Co Llc Lubricating members for razor cartridges.
EP3416484A1 (en) 2016-02-19 2018-12-26 Hazel Technologies, Inc. Compositions for controlled release of active ingredients and methods of making same
US20170334082A1 (en) 2016-05-18 2017-11-23 The Gillette Company Llc Skin Engaging Member Comprising Ethylene Vinyl Acetate
US20180117780A1 (en) 2016-11-03 2018-05-03 The Gillette Company Llc Skin engaging member comprising ethylene vinyl acetate
CN109843385B (en) 2016-11-17 2022-06-03 吉列有限责任公司 Skin engaging member comprising ethylene vinyl acetate and fragrance
JP7106262B2 (en) * 2017-10-31 2022-07-26 ロレアル Composition with cooling effect
CN112226054B (en) * 2020-09-09 2022-09-23 温州美葆剃须系统有限公司 Lubricating strip for shaver, preparation method of lubricating strip and shaver

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992005929A1 (en) * 1990-09-28 1992-04-16 The Gillette Company Shaving system
WO1994021225A1 (en) * 1993-03-24 1994-09-29 Jan Wadstein Skin care composition

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS55122709A (en) * 1979-03-13 1980-09-20 Asama Kasei Kk Stench remover from mouth
US4789559A (en) * 1981-02-12 1988-12-06 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Anhydrous crystals of maltitol and the whole crystalline hydrogenated starch hydrolysate mixture solid containing the crystals, and process for the production and uses thereof
US4356115A (en) * 1981-04-27 1982-10-26 Ichiro Shibanai Fragrant synthetic resin product and method of producing the same
US4678598A (en) * 1985-08-06 1987-07-07 Kao Corporation Liquid shampoo composition
HU201685B (en) * 1987-04-23 1990-12-28 Chinoin Gyogyszer Es Vegyeszet For producing pharmaceutical compositions for inhalation and compositions for scenting air containing volatile active component in cyclodextrine inclusion, and air-scenting composition
US5095619A (en) * 1990-09-28 1992-03-17 The Gillette Company Shaving system
US5165943A (en) * 1991-06-21 1992-11-24 Wm. Wrigley Jr. Company Cooling agent/cyclodextrin complex for improved flavor release
FR2705350B1 (en) * 1993-05-13 1995-07-07 Oreal New derivatives of mono (6-amino 6-deoxy) cyclodextrin substituted in position 6 by an alpha-amino acid residue, their preparation process and their uses.

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992005929A1 (en) * 1990-09-28 1992-04-16 The Gillette Company Shaving system
WO1994021225A1 (en) * 1993-03-24 1994-09-29 Jan Wadstein Skin care composition

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0827735A1 (en) 1996-09-04 1998-03-11 Warner-Lambert Company Shaving aid with physiological cooling effect
EP0835649A1 (en) * 1996-09-04 1998-04-15 Warner-Lambert Company Shaving aid with complexing agent
US7727516B2 (en) 2006-02-28 2010-06-01 The Procter & Gamble Company Reduction of hair growth
WO2011022321A2 (en) 2009-08-21 2011-02-24 The Gillette Company Hair removal device
EP2286788A2 (en) 2009-08-21 2011-02-23 The Gillette Company Hair removal device
WO2011022285A2 (en) 2009-08-21 2011-02-24 The Gillette Company Hair removal device
CN102481241A (en) * 2009-08-21 2012-05-30 吉列公司 Hair removal device
WO2011022285A3 (en) * 2009-08-21 2011-04-14 The Gillette Company Hair removal device
WO2011022321A3 (en) * 2009-08-21 2011-04-14 The Gillette Company Hair removal device
RU2485934C1 (en) * 2009-08-21 2013-06-27 Дзе Жиллетт Компани Device for hair removal
EP2286787A3 (en) * 2009-08-21 2012-10-24 The Gillette Company Hair removal device
EP2286788A3 (en) * 2009-08-21 2012-10-24 The Gillette Company Hair removal device
EP2286787A2 (en) 2009-08-21 2011-02-23 The Gillette Company Hair removal device
EP2361607A1 (en) 2010-02-18 2011-08-31 The Gillette Company Hair removal device comprising moisturizing compositions
WO2011103072A1 (en) 2010-02-18 2011-08-25 The Gillette Company Hair removal device comprising moisturizing compositions
WO2011102996A2 (en) 2010-02-18 2011-08-25 The Gillette Company Hair removal device comprising erodable moisturizer
WO2011103235A2 (en) 2010-02-18 2011-08-25 The Gillette Company Hair removal device comprising an erodable composition
EP2517693A1 (en) 2011-04-26 2012-10-31 The Gillette Company Hair removal device comprising a modifying surfactant
WO2012148939A2 (en) 2011-04-26 2012-11-01 The Gillette Company Hair removal device comprising a modifying surfuctant
EP2537511A1 (en) 2011-06-24 2012-12-26 The Gillette Company Hair removal device comprising erodable moisturizer
WO2012177979A2 (en) 2011-06-24 2012-12-27 The Gillette Company Hair removal device comprising erodable moisturizer
EP2591895A1 (en) 2011-11-10 2013-05-15 The Gillette Company Razor cartridge with lubrication and moisturizing strips
WO2013070995A1 (en) 2011-11-10 2013-05-16 The Gillette Company Razor cartridge with lubrication and moisturizing strips
WO2015148308A1 (en) * 2014-03-26 2015-10-01 The Gillette Company Skin engaging shavng aid comprising a thermally resilient sensate and a trpa1 receptor inhibitor

Also Published As

Publication number Publication date
EP0837760B1 (en) 1999-02-10
BR9609457A (en) 1999-03-02
ZA965481B (en) 1997-01-27
ATE176616T1 (en) 1999-02-15
JPH11508897A (en) 1999-08-03
AR002635A1 (en) 1998-03-25
ES2129980T3 (en) 1999-06-16
CA2224223C (en) 2002-11-26
AU695164B2 (en) 1998-08-06
EP0837760A1 (en) 1998-04-29
DE69601542D1 (en) 1999-03-25
AU6406296A (en) 1997-02-05
CA2224223A1 (en) 1997-01-23
DE69601542T2 (en) 1999-08-19
MX9800158A (en) 1998-03-31
CO4750633A1 (en) 1999-03-31
US5653971A (en) 1997-08-05

Similar Documents

Publication Publication Date Title
EP0837760B1 (en) Wet shavingsystem with shaving aid composite with an inclusion complex of a skin-soothing agent and cyclodextrin
EP0837759B1 (en) Wet shaving system with shaving aid composite with a non-volatile cooling agent
WO1997002116A9 (en) Shaving aid composite with a non-volatile cooling agent
CA2185682C (en) Shaving system
US5113585A (en) Shaving system
US5095619A (en) Shaving system
US5349750A (en) Shaving system
CA2171737C (en) Shaving system
EP0790883B1 (en) Skin engaging member
AU694054C (en) Shaving aid composite with a non-volatile cooling agent
CA2203897C (en) Skin engaging member
MXPA96004126A (en) System for afei

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AL AM AT AU AZ BB BG BR BY CA CH CN CZ DE DK EE ES FI GB GE HU IL IS JP KE KG KP KR KZ LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK TJ TM TR TT UA UG US UZ VN AM AZ BY KG KZ MD RU TJ TM

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): KE LS MW SD SZ UG AT BE CH DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 1996923589

Country of ref document: EP

ENP Entry into the national phase

Ref document number: 2224223

Country of ref document: CA

Ref document number: 2224223

Country of ref document: CA

Kind code of ref document: A

ENP Entry into the national phase

Ref document number: 1997 505273

Country of ref document: JP

Kind code of ref document: A

WWE Wipo information: entry into national phase

Ref document number: PA/A/1998/000158

Country of ref document: MX

WWP Wipo information: published in national office

Ref document number: 1996923589

Country of ref document: EP

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

WWG Wipo information: grant in national office

Ref document number: 1996923589

Country of ref document: EP