WO2004103314A2 - Produits pour soins personnels contenant un polyol polyester exempts de fluides de silicone a faible viscosite - Google Patents

Produits pour soins personnels contenant un polyol polyester exempts de fluides de silicone a faible viscosite Download PDF

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Publication number
WO2004103314A2
WO2004103314A2 PCT/US2004/016032 US2004016032W WO2004103314A2 WO 2004103314 A2 WO2004103314 A2 WO 2004103314A2 US 2004016032 W US2004016032 W US 2004016032W WO 2004103314 A2 WO2004103314 A2 WO 2004103314A2
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WO
WIPO (PCT)
Prior art keywords
personal care
acid
polyol
product
carbon atoms
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Application number
PCT/US2004/016032
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English (en)
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WO2004103314A3 (fr
Inventor
Rocco Burgo
Original Assignee
Inolex Investment Corp.
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Publication date
Application filed by Inolex Investment Corp. filed Critical Inolex Investment Corp.
Publication of WO2004103314A2 publication Critical patent/WO2004103314A2/fr
Publication of WO2004103314A3 publication Critical patent/WO2004103314A3/fr

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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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/007—Preparations for dry skin

Definitions

  • Silicone fluids are widely used in toiletries, cosmetics, and other personal care products. Most frequently used are the lower viscosity silicone fluids, such as dimethicones and the cyclomethicones. Incorporated into a product, these silicone fluids provide a variety of benefits such as improved slip, reduction of tack, impartation of emolliency, and other modifications of the "feel" characteristics of the formulation.
  • the lower viscosity silicone fluids have been considered to be particularly useful by personal care product formulators, as they tend to provide the aforementioned benefits without contributing to oiliness or greasiness, and give what may be considered to be a "dry" feel on skin.
  • the lower viscosity silicone fluids particularly the tetramer (D4) and the pentamer (D5) cyclomethicones are excellent dispersing and spreading agents, are generally water white in color, low in odor, have some degree of volatility, and are resistant to chemical and oxidative attack.
  • esters such as isopropyl laurate, isononyl isononanoate, and 2- ethylhexyl 2-ethylhexanoate.
  • esters provide some characteristics similar to the low viscosity silicone fluids; however, because they are monoesters, they tend to be slower spreading, oilier feeling, and may have a disagreeable odor when applied.
  • the invention includes a personal care product comprising: (a) at least one polyol polyester that is the esterification reaction product of a polyol having three to six carbons atoms and a carboxylic acid having three to six carbon atoms; and (b) a personal care formulation, but which does not contain a low viscosity silicone fluid.
  • a personal care product comprising: (a) at least one polyol polyester that is the esterification reaction product of a polyol having three to six carbons atoms and a carboxylic acid having three to six carbon atoms; and (b) a personal care formulation, but which does not contain a low viscosity silicone fluid and wherein the personal care product has a performance characteristic similar to a personal care composition that contains a low viscosity silicone fluid.
  • the invention provides methods of preparing a replacement composition to replace a lower viscosity silicone fluid in a personal care composition, the replacement composition comprising at least one polyol polyester that is the esterification reaction product of a polyol having three to six carbons atoms and a carboxylic acid having three to six carbon atoms and having a. kinematic viscosity of about 2 to about 20 centistokes at 25 ° C and wherein the replacement composition does not contain a low viscosity silicone fluid.
  • a method of preparing a personal care product comprises blending at least one polyol polyester that is the esterification reaction product of a polyol having three to six carbons atoms and a carboxylic acid having three to six carbon atoms with a personal care formulation, wherein the personal care product does not contain a lower viscosity silicone fluid.
  • the invention includes replacement compositions that may be incorporated into personal care products, personal care products containing the replacement compositions, and methods of preparing both the replacement composition and the personal care products.
  • the replacement composition comprises certain polyol polyesters that compare favorably in performance properties (such as viscosity, spreading rate, and feel characteristics when incorporated into personal care products) with the characteristics of the lower viscosity silicone fluids.
  • performance properties such as viscosity, spreading rate, and feel characteristics when incorporated into personal care products
  • one may prepare personal care products that, to the end user, feel, apply, and perform like the lower viscosity silicone fluid-containing products.
  • personal care product any composition that is used or marketed as a material to be applied to the skin, hair, or nails, and/or the stratum corneum of human or animal subjects for cosmetic, aesthetic and/or therapeutic effects, regardless of the delivery form of the composition, and may include phases or intermediate preparations ultimately formulated into personal care products.
  • Such products can include grooming products, such as soaps, cleansers, shampoos, skin or hair conditioners, shaving creams, lotions, and gels; hair sprays, gels, tonics, mousses, pomades, and lacquers; antiperspirants and deodorants; skin lotions, creams, mousses, and ointments, and nail and cuticle care products, such as polishes and creams.
  • the methods, replacement compositions, and personal care products of the invention each include one or more polyol polyesters derived from the esterification reaction of a polyol having about three to about six carbon atoms (C 3 to C 6 ) with a carboxylic acid having about three to about six carbon atoms (C 3 to C 6 linear or branched carboxylic acid).
  • Polyols having one, two, three, four, five, six, seven, eight or nine carbon atoms may be preferred.
  • the polyols may be branched or unbranched, substituted or unsubstituted.
  • the selected carboxylic acids one may also use those having one, two, three, four, five, six, seven, eight, or nine carbon atoms.
  • the selected carboxylic acid(s) may be branched or unbranched, substituted or unsubstituted.
  • the characteristics desired in the end polyol polyester such as flow properties like viscosity, viscosity temperature behavior, spreading rate, and skin feel properties, can be modified by a variance in selection and/or combination of the polyol(s) and carboxylic acid(s) used to prepare the polyol polyester. For example, to obtain low viscosity and low odor, diols having three to six carbon atoms may be preferred.
  • Examples of preferred carboxylic acids for use may be, without limitation, propanoic acid, butyric acid, 2-methyl propanoic acid, 2-methyl butyric acid, isopentanoic acid, pentanoic acid, hexanoic acid, 2-ethyl butyric acid, and 2-methyl pentanoic acid.
  • the polyol polyester may be one having a structure represented by formula (I):
  • R 1 is an aliphatic hydrocarbon of two to five carbon atoms and R 2 is an aliphatic hydrocarbon of three to six carbon atoms, and which contains zero to three ether linkages.
  • One exemplary polyol polyester for use in the replacement compositions of the invention may be neopentyl glycol dipentanoate.
  • Neopentyl glycol dipentanoate is a water white, odorless liquid with the viscosity of 5.1 centistokes at 25° C. NDP is a rapidly spreading liquid and provides a dry initial feel, and a soft silky, smooth, powdery after feel.
  • personal care formulations it is meant any formulations known or to be developed in the art for personal care products. Exemplary formulations include those for soap (liquid, solid, foam, or mousse), cleansers, creams, lotions, ointments, suspensions, shampoos, deodorants, antiperspirants, conditioning products for hair, skin, and nails, and decorative cosmetics (i.e., those that impart color to the hair, skin, or nails upon application).
  • the personal care formulations used in the invention may include organic or inorganic components; color active ingredients (e.g., pigments and dyes); therapeutic active ingredients (e.g., vitamins, alpha hydroxy acids, corticosteroids, amino acids, collagen, retinoids, antimicrobial compounds), sunscreens and/or UV absorbing compounds, reflective compounds, oils such as castor oil and olive oil; film formers, high viscosity oils, high molecular weight esters, antiperspirant active ingredients, glycol solutions, water, alcohols, emulsifiers, gellants, emollients, water, polymers, hydrocarbons, conditioning agents, and/or aliphatic esters.
  • color active ingredients e.g., pigments and dyes
  • therapeutic active ingredients e.g., vitamins, alpha hydroxy acids, corticosteroids, amino acids, collagen, retinoids, antimicrobial compounds
  • sunscreens and/or UV absorbing compounds e.g., sunscreens and/or UV absorbing compounds, reflective compounds,
  • Exemplary pigments and/or dyes include but are not limited to, titanium dioxide, iron oxides, zinc oxides, ultramarine blue, manganese violet, mica powder, barium lake, calcium lake, aluminum lake, FD&C yellow, FD&C green, FD&C blue, and FD&C red.
  • Suitable conditioning agents especially for use in hair conditioning formulations, may include polyquaternium polymers, alkamidopropyldimethyl amines, alkylfrimonium chlorides, alkyltrimonium methyl sulfates, and ester quaternaries.
  • Exemplary high molecular weight esters include pentaerythritol, tetraisosterate (such as CRODAMOL ® PTIS, Croda Corporation, Parsippany, New Jersey, United States of America) and dipentaerythritol hexa C 5 -C 9 acid esters (such as LEXFEEL 350, Inolex Chemical Company, Philadelphia, Pennsylvania, United States of America).
  • tetraisosterate such as CRODAMOL ® PTIS, Croda Corporation, Parsippany, New Jersey, United States of America
  • dipentaerythritol hexa C 5 -C 9 acid esters such as LEXFEEL 350, Inolex Chemical Company, Philadelphia, Pennsylvania, United States of America.
  • it may be desirable to disperse the color active ingredients e.g., opaque or translucent pigments or dyes
  • high viscosity oils such as a castor oil.
  • Typical film formers that can be used in the personal care formulation components of the invention include acrylate copolymers (such as AVALURE AC 120, Noveon Corporation, Cleveland, Ohio, United States of America), tricontanyl PDP (such as GANEX ® WP-660, ISP Corporation, Wayne, New Jersey, United States of America), alpha-olefin (isopropyl maleate copolymer) (such as PROFORMA ® V1608, New Faith Technologies, Sugarland, Texas, United States of America).
  • film formers will be included in the formulation when preparing a product intended to smooth out surface irregularities in the stratum corneum and to provide a stable immovable matrix for any color active ingredients to be included.
  • the personal care formulation may be an antiperspirant including inorganic salts and/or inorganic salt/glycine complexes.
  • antiperspirant active ingredients include, but, are not limited to, activated aluminum chlorohydrate (“AACH”), aluminum zirconium polychlorhydrex/glycine complex (“ZAG”) or activated ZAG (“AZAG”).
  • AACH activated aluminum chlorohydrate
  • ZAG aluminum zirconium polychlorhydrex/glycine complex
  • AZAG activated ZAG
  • the antiperspirant active ingredient may be provided to the formulation in any form, including a powder, an aqueous solution, or a glycol solution, such a propylene glycol, 1,3-butylene glycol, and dipropylene glycol.
  • the formulation of clear antiperspirant gels will include the combination of an active ingredient phase and a vehicle phase.
  • the active ingredient phase will normally include one or more of the previously mentioned antiperspirant active ingredients, either dissolved or pre- dissolved in water, propylene glycol, other glycols, or mixtures thereof.
  • the vehicle phase will typically include an emulsifier, gellant, and a mixture of oily ingredients that are meant to ease the spreading of the antiperspirant on to the skin, and to reduce the feeling of drag, greasiness, and/or tackiness.
  • the polyol polyester is formed by reacting a C 3 -C 6 polyol as described above with a C -C 6 carboxylic acid to form a replacement composition that duplicates the spreading weight, viscosity, volatility, and/or skin feel of the lower viscosity silicone fluids. In this way, a replacement composition is provided.
  • the reaction may be accomplished by any reaction protocol known or developed in the art.
  • the presence of at least two polar ester linkages in the finished polyol polyester provides the low volatility, low odor, and fast spreading rate on the skin.
  • the specific carbon content of the polyols and carboxylic acids of C 3 -C 6 provides the low viscosity necessary to match the lower viscosity silicone fluids, particularly the tetramer (D4) and pentamer (D5) cyclomethicone fluids.
  • D4 and D5 tetramer
  • D5 pentamer
  • two or more polyol polyester(s) may be blended; however in the actual practice of cosmetic and toiletry product formulation this is not ordinarily necessary.
  • the personal care products of the invention can be prepared by mixing the replacement composition with a personal care formulation. Such blending may be accomplished by any means known in the art. Suitable means include mixing, blending, high sheer mixing, stirring, shaking or agitating. [0027] Kinematic viscosity was tested at 25° C using ASTM (American Society of Testing and Materials, West Conshohocken, Pennsylvania, United States of America) Official Method No. D- 445-97 (1997), the contents of which are incoiporated herein by reference.
  • the spreading characteristics of fluid used in personal care products are an effective predictor of "skin feel.”
  • a four inch WHATMAN ® filter paper was positioned horizontally over an eight ounce jar. Fifty microliters of each product were then pipetted onto the center of the filter paper. The spreading area of the liquid was then measured at intervals of one, three, and five minutes. Faster spreading products will have a higher spreading area at each time interval.
  • CTFA Cosmetic, Toiletry, and Fragrance Association
  • Neopentyl glycol and n-pentanoic acid were charged to a stirred batch reactor in a molar ratio of 1:1.3 and heated with inert gas sparging to approximately 120° C to 200° C in the presence of a small quantity of a catalyst (0.1 wt% sulfonic acid). The hydroxyl value was monitored, and the reaction was stopped before the hydroxyl value reached three. The majority of the residual carboxylic acid was removed under reduced pressure. Remaining trace acid was neutralized with a sodium carbonate solution and the polyol polyester was then batch distilled. The distillate was then deodorized by steam stripping, and further purified with activated clay. It was then filtered. Table 1, below, shows the properties of the replacement composition obtained. Table 1: Properties of the replacement composition.
  • Neopentyl glycol and 2-ethylbutyric acid were charged to a stirred batch reactor in a molar ratio of 1 : 1.5 and heated with inert gas sparging to 120° to 200° C in the presence of a small quantity of a catalyst (0.1 wt% sulfonic acid). The hydroxyl value was monitored, and the reaction was stopped when the hydroxyl value reached three or lower. The majority of the residual carboxylic acid was removed under reduced pressure. Remaining trace acid was neutralized with a sodium carbonate solution, and the ester was then batch distilled. The distillate was then deodorized by steam stripping, and further purified with activated clay. It was then filtered. Table 3 shows the properties of the replacement composition, neopentyl glycol di-2-ethylbutyrate ("ND2EB").
  • ND2EB neopentyl glycol di-2-ethylbutyrate
  • Table 3 Properties of Replacement Composition That Is ND2EB Ester.
  • a silicone-free antiperspirant stick personal care product was prepared using the replacement composition of the invention. Hydrogenated castor oil 2.5 g, stearyl alcohol 818.0 g and polypropylene glycol- 14 butyl ether 9 g were combined in a vessel and warmed to approximately 80° to 85° C under gentle agitation until a clear solution was obtained. Subsequently, the mixture was allowed to cool to approximately 70° C.
  • the replacement composition of Example 5, 43 g was warmed to approximately 70° C and was added to the mixture. Maintaining the temperature at 70° C, talc 3 g, aluminum zirconium tetrachlorohydrex/glycine 24 g and amoiphous fumed silica 0.5 g were added. The entire mixture was agitated until approximately uniformly mixed, then it was cooled to approximately 60° C. The resulting mixture was poured into canisters and allowed to cool to room temperature.
  • a silicone-free moisturizing lotion personal care product was prepared.
  • Deionized water 81.5 g, glycerin 3.0 g, and acrylates/C 10-20 alkyl acrylate cross polymer (PEMULEN ® TR-1, available from Noveon Corporation, Cleveland, Ohio, United States of America), 0.2 g were combined in a vessel under agitation.
  • PEMULEN ® TR-1 acrylates/C 10-20 alkyl acrylate cross polymer
  • Glyceryl stearate and) polyethylene glycol- 100 stearate (and) behenic acid (and) stearyl alcohol (and) behenamidopropyl PG dimonium chloride 1.5 g, glyceryl dilaurate 1.0 g, stearic acid 0.5 g and the replacement composition of Example 5, 10 g, were combined in a separate vessel and warmed to 70° to 75° C under gentle agitation until a uniform dispersion was obtained. The contents of the first vessel were added to the second and the mixture was allowed to cool to approximately 60° C. The pH of the mixture was determined and was adjusted to approximately 6.0 with triethanolamine. The resulting mixture was then poured into containers and permitted to cool to room temperature.
  • Example 9 Preparation of a Silicone-Free After-Bath Moisturizing Body Oil Personal Care Product
  • a silicone-free after-bath moisturizing body oil personal care product was prepared. First, trimethylolpropane tricaprylate/tricaprate lOg, mineral oil 32 g, the replacement composition of Example 5, 56 g, and a fragrance 2 g were combined under agitation while being heated to approximately 45° C. The mixture is agitated under these conditions until a clear solution is obtained. The mixture is then poured into containers and permitted to cool to room temperature.
  • Example 10 Preparation of a Silicone-Free Moisturizing Body Oil
  • Jojoba oil 20 g, tocopheryl acetate 0.5 g, BHT 0.1 g, isopropylpalmitate 5.0 g, and the replacement composition of Example 1 74 g and a fragrance 0.4 g were combined under agitation in a vessel and heated to approximately 45° C. The mixture was agitated until a clear solution was obtained. It was then poured into containers and allowed to cool to room temperature.
  • Example 11 Example 11
  • An antiperspirant stick personal care product was prepared. Hydroxy stearic acid and the replacement composition of Example 3 were combined in a vessel and warmed to 83° C under gentle agitation until a clear solution was obtained. Subsequently, the mixture was allowed to cool to approximately 70° C. Aluminum zirconium tetrachlorohydrex/glycine 24 g, talc 6 g, and silica 4 g were added. The mixture was agitated until uniform and then was cooled to approximately 60° C. The first mixture was then added to the second mixture, and mixed and combined thoroughly. The resulting mixture was poured into canisters and allowed to cool to room temperature.
  • a personal care product that is a light lotion that does not contain a silicone yet provides silicone-like aesthetics was prepared.
  • Deionized water 77.52 g, acrylates/C 10-30 alkyl acrylate cross polymer 0.1 g, disodium EDTA 0.15 g, methylparaben 0.25 g, propylparaben 0.05 g were combined in a vessel and warmed to approximately 73° C under vigorous agitation until a clear, uniform solution was obtained.
  • Glyceryl stearate (and) polyethylene glycol-100 stearate 3.0 g, glyceryl stearate 2.0 g, cetearyl alcohol 1.5 g and DEG/C6 ester 15 g were combined in a separate vessel and warmed to approximately 73° C until a clear solution was obtained.
  • the second solution was added to the first solution under high sheer mixing. The high sheer mixer is stopped and a 10% aqueous solution of sodium hydroxide 0.43 g was added under gentle agitation. The heating was stopped and the solution was allowed to cool to room temperature under gentle agitation. The resulting emulsion was poured into canisters.

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  • Life Sciences & Earth Sciences (AREA)
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Abstract

L'invention concerne un produit pour soins personnels exempt de fluide de silicone à faible viscosité. Ce produit pour soins personnels comprend au moins un polyol polyester qui est le produit de réaction d'estérification d'un polyol renfermant entre 3 et 6 atomes de carbone et d'un acide carboxylique renfermant entre 3 et 6 atomes de carbone, ainsi qu'une préparation pour soins personnels. L'invention concerne également des compositions de remplacement destinées à des produits pour soins personnels comprenant au moins un polyol polyester qui est le produit de réaction d'estérification d'un polyol renfermant entre 3 et 6 atomes de carbone et d'un acide carboxylique renfermant entre 3 et 6 atomes de carbone, et présentant une viscosité cinématique comprise entre environ 2 et environ 20 centistokes à 25 °C, la composition de remplacement ne contenant pas de fluide de silicone à faible viscosité. L'invention se rapporte en outre à des procédés associés.
PCT/US2004/016032 2003-05-20 2004-05-20 Produits pour soins personnels contenant un polyol polyester exempts de fluides de silicone a faible viscosite WO2004103314A2 (fr)

Applications Claiming Priority (2)

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US47209703P 2003-05-20 2003-05-20
US60/472,097 2003-05-20

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WO2004103314A2 true WO2004103314A2 (fr) 2004-12-02
WO2004103314A3 WO2004103314A3 (fr) 2005-08-11

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2767271A4 (fr) * 2011-10-11 2015-05-27 Jun-Hong Chi Composition cosmétique obtenue par estérification d'alcool amylique ou d'un isomère de celui-ci et acide gras d'huile végétale naturelle

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5624676A (en) * 1995-08-03 1997-04-29 The Procter & Gamble Company Lotioned tissue paper containing an emollient and a polyol polyester immobilizing agent
US5705164A (en) * 1995-08-03 1998-01-06 The Procter & Gamble Company Lotioned tissue paper containing a liquid polyol polyester emollient and an immobilizing agent

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5624676A (en) * 1995-08-03 1997-04-29 The Procter & Gamble Company Lotioned tissue paper containing an emollient and a polyol polyester immobilizing agent
US5705164A (en) * 1995-08-03 1998-01-06 The Procter & Gamble Company Lotioned tissue paper containing a liquid polyol polyester emollient and an immobilizing agent

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2767271A4 (fr) * 2011-10-11 2015-05-27 Jun-Hong Chi Composition cosmétique obtenue par estérification d'alcool amylique ou d'un isomère de celui-ci et acide gras d'huile végétale naturelle

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