Classifications

• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
  • C11D1/88—Ampholytes; Electroneutral compounds
  • C11D1/90—Betaines
• • 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
  • 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
  • A61K8/60—Sugars; Derivatives thereof
  • A61K8/604—Alkylpolyglycosides; Derivatives thereof, e.g. esters
• • 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
• • 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
  • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
  • A61K8/8164—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers, e.g. poly (methyl vinyl ether-co-maleic anhydride)
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
  • C11D3/16—Organic compounds
  • C11D3/37—Polymers
• • 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
  • A61K2800/74—Biological properties of particular ingredients
  • A61K2800/75—Anti-irritant
• • 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
  • A61Q19/10—Washing or bathing preparations

Definitions

• milder cleansing compositions have included combining relatively low amounts of anionic surfactants (which tend to be relatively high- foaming but also relatively highly irritating), with relatively lower irritating surfactants such as nonionic and/or amphoteric surfactants. See, e.g. United States Patent No. 4,726,915.
• Another approach to producing mild cleansing compositions is to associate the anionic surfactants with amphoteric or cationic compounds in order to yield surfactant complexes. See, e.g., United States Patent Nos. 4,443,362; 4,726,915; 4,186,1 13; and 4,110,263. Disadvstromously, mild cleansing compositions produced via both of such methods tend to suffer from relatively poor foaming and cleansing performance.
• Yet another approach described in, Librizzi et al., discusses the use of a composition including both a hydrophobically modified polymer and a surfactant to provide low irritation cleansing composition.
• provided are methods of making personal care compositions comprising combining a polymerized surfactant having a PMOD% of less than about 90% with at least one other personal care component to produce a personal care composition having a CMID% of less than about 90%.
• hydrophilic moiety is any anionic, cationic, zwitterionic. or nonionic group that is polar and generally water-soluble.
• anionics such as sulfate, sulfonate, carboxylate, phosphate, phosphonates
• cationics such as: ammonium, including mono-, di- , and trialkylammonium species, pyridinium, imidazolinium, amidinium, poly(ethyleneiminium)
• zwitterionics such as ammonioalkylsulfonate, ammonioalkylcarboxylate, amphoacetate: and nonionics such as hydroxyl, sulfonyl, poly(ethyleneoxy).
• TEP value associated with a particular composition, which value is measured conventionally via the Trans-Epithelial Permeability Test ("TEP Test") as set forth in the Invittox Protocol Number 86 (May 1994) incorporated herein by reference and described in further detail in the Examples below, has a direct correlation to the irritation to the skin and/or eyes associated with the composition. More specifically, a higher TEP value of a composition tends to indicate less irritation to the skin and eyes associated therewith as compared to a composition having a lower TEP value, which composition tends to cause higher levels of irritation to the skin and/or eyes. Applicants have recognized that the present compositions have surprisingly high TEP values/lower irritation associated therewith.
• Figure l is a graph 10 showing a micelle size distribution function for a typical conventional surfactant system, a composition including sodium laureth sulfate and cocamidopropyl betaine (curve 11, generated by fitting an idealized log normal distribution to actual data obtained by testing Comparative Example 19).
• Applicants have discovered, by comparison, that low-DP polymerized surfactants of the present invention are capable of providing a distribution of micelles that, as shown in curve 15, is "shifted" to favor larger micelles (curve generated by fitting an idealized log normal distribution to actual data obtained by testing Example 12).
• the present invention allows for the production of compositions that exhibit not only reduced irritation, but also desirable rheology properties.
• ingredients such as hydrophobically modified polymers tend to increase the viscosity and the yield point associated with a composition as more polymer is added
• the polymerized surfactants of the present invention tend to have relatively small effect on the rheology of the compositions to which they are added. Accordingly, in certain embodiments, higher amounts of the present polymers may be added to more significantly reduce irritation without producing a composition that is too viscous for effective personal use.
• Subclass (A) Homopolymerization of prefabricated reactive amphiphiles containing ethylenically unsaturated functionalities (hereinafter "EUAHs").
• EUAHs ethylenically unsaturated functionalities
• R3 are independently H or CH3, R 2 comprises Hphil, and R 4 comprises Hphob group, or
• R 4 H or CH S
• X O or NH
• R 5 any linear or branched carbon chain containing more than 5 carbon atoms
• M H + , NH 4 + , or any Group IA alkali metal cation.
• Allylalkylsulfosuccinates e.g. sodium allyldodecylsulfosuccinate (TREM LF-40, Cognis)
• R 8 any linear or branched carbon chain containing 5 or less carbon atoms
• Rg H. CH 3 , CH 2 CH 3 or CH 2 CH 2 OH
• Rio any linear or branched carbon chain containing more than 5 carbon atoms
• X O or NH.
• Rg any linear or branched carbon chain containing more lhan 5 carbon atoms.
• R 9 . R )0 are independenly H, CH 3 . CH 2 CH 3 or CH 2 CH 2 OH.
• Z any Group VIl-A halide anion Quaternized vinylpyridines: e.g. (4-vinyl)dodecylpyridinium bromide
• Alkyldiallylmethylammonium halides e.g. diallyldodecylmethylammonium chloride
• R 27 H. CH 3 . or CH 2 COOH
• X O
• R 2 g any linear or branched carbon chain more than 5 carbon atoms
• n is an integer from about 4 to about 800
• R 5 , R 6 are independently H or CH3, R 7 comprises HPhil group, and R R comprises HPhil group
• R 5 , R 7 are independently H or CH 3 , K(, comprises HPhil group, and Rg comprises HPhil group
• K t , R 7 are independently H or CH3, R5 comprises HPhil group, and Rg comprises HPhil group to yield a polymerized surfactant with an amphiphilie repeat unit shown in brackets immediately below, and having a number of amphiphilie repeat units, n and a number of non-amphiphilic repeat units, m:
• compositions of the present invention comprise from about 0.5 to about 15%, more preferably from about 1.5 to about 10%, even more preferably from about 2 to about 7%, even more preferably from about 3 to about 7% of active polymerized surfactant in the composition.
• compositions useful in the present invention may also include any of a variety of monomeric surfactants.
• monomeric surfactants it is meant any surface active agents that do not meet the definition of "polymerized surfactant” as defined above.
• the monomeric surfactants may be anionic, nonionic, amphoteric or cationic. examples of which are detailed below.
• alkyl sulfos ⁇ ccinates of the formula:
• amphoteric surfactants suitable for use in the present invention include, but are not limited to, amphocarboxylates such as alkyl amphoacetates (mono or di); alkyl betaines; amidoalkyl betaines; amidoalkyl sullaines: amphophosphates; phosphorylaied imidazolines such as phosphobetaines and pyrophosphobetaines; carboxyalky] alkyl polyamines; alkylimino-dipropionates: alkylamphoglycinates (mono or .
• amphocarboxylate compounds include those of the formula: R 7 wherein
• Rs is hydrogen or a carboxyalkyl group containing from about 2 to about 3 carbon atoms
• Re is an alkylene group having from about 2 to about 3 carbon atoms and n is 1 or 2;
• Rg and Rio are each independently an alkyl or hydroxyalkyl group having from about 1 to about 4 carbon atoms: and p is 1 or 2.
• Rn and Ru are each independently an alkyl or Hydroxyalkyl group having from about 1 to about 4 carbon atoms; q is an integer from about 2 to about -6; and m is 1 or
• amidoalkyl betaine is cocamidopropyl betaine, available commercially from Degussa Goldschmidi Chemical Corporation of Hopewell. Virginia under the tradename, 'Tegobetaine L7.”
• R] 6 is hydrogen or a carboxyalkyl group containing from about 2 to about 3 carbon atoms:
• R is is an alkylene or hydroxyalkylene group having from about 2 to about 3 carbon atoms.
• E. r. R 1 , R 2 and R 3 are as defined above.
• the pyrophosphobetaine compounds are those disclosed in U.S. Patent Nos. 4,382,036, 4.372.869. and 4.617,414, which are all incorporated herein by reference.
• the pearlescent or opacifying agent may be introduced to the mild cleansing composition as a pre-formed, stabilized aqueous dispersion, such as that commercially available from Cognis Corporation of Ambler. Pennsylvania under the tradename, "Euperlan PK-3000. " This material is a combination of glycol distearate (the diester of ethylene glycol and stearic acid), Laure ⁇ h-4 and cocamidopropyl betaine and may be in a weight percent ratio of from aboui 25 to about 30: about 3 to about 15: about 20 to about 25, respectively.
• Suitable preservatives include, for example, parabens, quaternary ammonium species, phenoxyethanol, benzoates, DMDM hydanloin, and are present in the composition in an amount, based upon the total weight of the composition, from about 0 to about 1 percent or from about 0.05 percent to about 0.5 percent.
• the polymerized surfactant, optional monomelic surfactants and optional other components of the composition may be combined according to the present invention via any conventional methods of combining two or more fluids or solids.
• one or more compositions comprising, consisting essentially of, or consisting of at least one polymerized surfactant and one or more compositions comprising, consisting essentially of, or consisting of water, monomelic surfactants or suitable ingredients may be combined by pouring, mixing, adding dropwise, pipetting, pumping, and the like, one of the compositions comprising the polymerized surfactant into or with the other in any order using any conventional equipment such as a mechanically stirred propeller, paddle, and the like.
• DLS Dynamic light scattering
• PCS Photon Correlation Spectroscopy
• this type of interference will lead to an erronously large measured value of micelle dn-
• additives exhibiting large values of d» should be separated from the sample via filtration or uhracenirifusaiion prior to determination of the micelle d» of the sample.
• higher order analysis of the DLS data using the Dispersion Technology Software v4.10 package may also be employed to obtain enhanced resolution and properly characterize micelle d» in the presence of nonmicellar scattering species.
• Foam Tesi was performed on various personal care compositions to determine the Maximum Foam Volume upon agitation according to ihe present invention. The procedure was accomplished by adding 5.0 grams of the model solution that included a particular polymerized surfactant to be tested, to 995 grams of deionized water and mixing until homogenous. The mixture was then added to a sample tank of a Sita R-2000 foam tester (commercially available from Future Digital Scientific, Co.; Bethpage, NY).
• Foam Volume data was collected at each stir cycle and the average and standard deviation of the three runs was determined. Maximum Foam Volume was reported for each Example as the value after the twelfth stir cycle.
• Citric A ⁇ d solution (20%) CHric ADd q s I qs q s qs qs ' qi
• the low-DP polymerized surfactants noted in Table 1 were prepared as follows: PA- 18. hydrolyzed, of Example El was obtained by performing a reaction of a 1:1 alternating copolymer of 1-octadecene and maleic anhydride (PA-18 Low Viscosity Low Color grade, commercially available from Chevron Phillips Chemical, LLC) with sodium hydroxide in aqueous solulion to yield a octadecene/MA copolymer having an average of approximately 25-75 amphophilic repeat units on a weight average basis, a mole fraction of amphiphilic repeal units of about 100%, and a hydrophobic group of C16 within the amphiphilic repeat unit.
• PA-18 Low Viscosity Low Color grade commercially available from Chevron Phillips Chemical, LLC
• Poly(acrylic acid co-2-acrylamidododecylsulfonic acid) of Example E5 was prepared via the free-radical copolymerization of acrylic acid and acryloyldecyltaurine in aqueous solution.
• Acryloyldecyltaurine is prepared according to the procedure of Harrison, K. S. (ref. US 3.544,597).
• the resulting copolymer had a weight average of approximately 10-500 amphiphilic repeat units, a mole fraction of amphiphilic repeat units of about 50%, and a hydrophobic group of Cl 2 within the amphiphilic repeat unit.
• compositions prepared in accordance with Examples El - E8 were tesied for mildness in accordance with the TEP Test described above. The samples were also tested according Io the DLS test. The results of ihese tests are listed below in Table 2:
• compositions tested As seen in Table 11 , for compositions tested, it can be see the polymerized surfactant, PA-] 8, hydrolyzed can be formulated into cleansing compositions with a variety of relative concentration of monomeric surfactant to polymerized surfactant.
• the compositions have a surprisingly low small micelle fractions as indicated by CMID% (less than about 90%), especially when compared with similar compositions with conventional surfactants, shown in Table 12.
• CMID% less than about 90%
• compositions tested As seen in Table 14, for compositions tested, it can be see the polymerized surfactant, PA-] 8. hydrolyzed can be formulated into cleansing compositions with a variety of total surfactant concentrations (polymerized + monomelic). In each of the examples, the compositions has a surprisingly low small micelle fractions as indicated by CM1D% (less than about 90%).

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• 2006
  • 2006-05-05 US US11/429,503 patent/US7417020B2/en not_active Expired - Fee Related
• 2007
  • 2007-03-28 CA CA002651298A patent/CA2651298A1/en not_active Abandoned
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