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`CLASS
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`INTERNATIONAL CLASSIFICATION
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`LJ The terminal months ol
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`s .TehJ
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`,{!r"
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`SUPERVISONY-PA1EI-fT
`TECHNSL6GV niuTFA 1600
`
`(Primary Examiner)
`
`(Date)
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`ISSUE BATCH NUMBER
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`PATENT APPLICATION
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`il||ililil tilil til] ililililil iltil ilililil ilt|
`09558466
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`
`CONTENTS
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`PATENT APPLICATION SERIAL NO.
`
`U.S. DEPARTMENT OF COMMERCE
`PATENT AND TRADEMARK OFFICE
`FEE RECORD SIIEET
`
`)
`
`I
`
`;Hil'%..ffi** o8's6
`
`PTO-1556
`(s/87)
`
`'U.S. GPO: 1 999-4Se{!Zt9t44
`
`3
`
`
`
`1
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`,]Y"
`
`| ilffi |||t ffit tff ilil tffit flil lffi t[ tilt ilil ililt [[]
`Bib Data Sheet
`
`SERIAL NUMBER
`09/558,466
`
`FILING DATE
`04t25t2000
`
`RULE
`
`\PPLISAN Il'
`David Scott,,Dunlop, Mason, OH ;
`Vicente Eduatdo Leyba, Cincinnati, OH ;
`
`filel / / c:/ APPS r'reexarn/conespondence/ l.htm
`
`UNITED STATES DEPARTMENT OF COMMERGE
`Patent and Trademark Ollice
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`washingron; D.C. 20231
`
`CLASS
`424
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`GBOUP ART UNIT
`1615
`
`ATTORNEY
`DOCKET NO.
`7543M
`
`z,x'o'
`
`a/'
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`SHEETS
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`TOTAL
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`* coNTINUING DATA **.*******.**************
`THIS APPbN'CmtUS BENEFTT OF 60/132,868 05/03/1999
`- FOREIGN APPLICATION9*********************
`nUX
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`/eriried and
`ff^\
`\cknowledoed ffi
`ADDRESS
`
`STATE OR
`COUNTRY
`OH
`
`\ndrew A Paul-Box 325
`fhe. Procter & Gamble Company
`iharon Woods Technical Center
`11511 Reed Hartman Highway
`lincinnati .OH 45241
`
`NTLE
`
`\nti-dandruff and conditioning shampoos containing certain cationic polymers
`I nltF"".
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`UTILITY
`No.7543M
`rE !
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`First Inventor or Application ldentifier I Dnid Scott Dunlop rt ol. -E
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`ANTr-DANDRUFF AND CONDTTTONTNG SHAMPOOS Ul<g
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`Case 7543M
`
`ANTI.DANDRUFF AND CONDITIONING SHAMPOOS
`CONTAINING CERTAIN CATIONIC POLYMERS
`
`David Scott DunloP
`VicenteEduardolevba
`
`4g?,? 6S N oslartqqq
`
`- -tL n?li,,*^k..'04^L'* ["""t'|* 4 6o'
`The present invention relates to shampoo compositions which provide a superior
`combination of anti-dandruff effrcacy and conditioning. These compositions contain anionic
`surfactants, conditioning agents, antldandruff particulates, cationic polymers, and water' The
`cationic polymers have certain molecular weight and charge density parameters that provide
`improved efficacy of anti-dandruff shampoo compositions.
`
`BACKGROUND OF THE INVENTION
`Shampoo compositions comprising various combinations of detersive surfactants and
`conditioning agents, especially silicone conditioning agents, are known in the art and are
`commercially available. Many of these compositions have been found to provide excellent hair
`cleansing and conditioning performance. For example, Pantene@ Shampoo Plus Pro-Vitamin
`Conditioner-in-One formulas which contain anionic surfactants, a cationic polymer and silicone
`conditioning agents provide excellent cleaning, conditioning and hair feel benefits upon application
`
`to hair.
`
`Anti-dandruffshampoos are also well known in the art and are also commercially available.
`Anti-dandruff shampoos typically incorporate an antidandruff active and detersive surfactants'
`Among the preferred type of anti-dandruff agents are particulate, crystalline anti-dandruff agents,
`such as sulfur, selenium disulfide and heavy metal salts of pyridinethione. Soluble anti-dandruff
`agents, such as ketoconazole, are also known in the art.
`Anti-dandruffshampoos which also provide conditioning benefits are likewise known in the
`art. For example, U.S. Pat. No. 5,624,666 exemplifies and claims shampoo compositions which
`contain anionic surfactants, cationic polymers and zinc pyridinethione as an anti-dandruff agent.
`U.S. pat. No. 5,624,666 teaches that conditioning agents such as silicone fluids can optionally be
`incorporated into the compositions therein. Head & Shoulders@ Dandruff Shampoo Plus
`
`I
`Ia
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`20
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`30
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`7
`
`
`
`Conditioner is an example of a marketed product which provides both anti-dandruff and conditioning
`
`benefits upon application of the shampoo to hair.
`
`Nevertheless, some consumers desire a shampoo which provides a superior combination of
`anti-dandruff efficacy and conditioning performance versus currently marketed products. Such a
`
`superior combination of efficacy and conditioning can be difficult to achieve.
`For example, it was previously believed that excellent anti-dandruff efficacy could be
`achieved by utilizing coacervate optimized for deposition efficiency on the hair and scalp.
`Coacervates that deposited more efficiently were thought to be prefened for efficacy. Unfortunately,
`the use of the most efficient coacervates to deposit anti-dandruff actives on the hair or scalp can
`negatively affect conditioning, specifically clean hair feel. In order to achieve good conditioning, the
`level of anti-dandruff agent could be reduced, resulting in good conditioning, but less than optimal
`
`l0
`
`anti-dandruff effi cacy.
`
`Applicants have now discovered, however, that, surprisingly, bioavailabilitv and coverase
`
`of the anti-dandruff active are much more predictive of efficacy than efficiency of deposition of the
`
`15
`
`active on the hair or scalp. In fact, Applicants have found that, in some cases, even when an anti-
`
`dandruff active deposited very well on the hair and scalp, acceptable anti-dandruff efficacy was not
`
`achieved. Conversely, good anti-dandruff efficacy could be achieved in situations where the anti-
`
`dandruff active had good coverage and was highly bioavailable, but did not deposit superiorly to the
`hair or scalp. Thus, in order for a shampoo composition to provide a superior combination of anti-
`
`dandruff efficacy and conditioning compared to known shampoo compositions, it must meet certain
`criteria with respect to bioavailability and coverage, but it does not necessarily have to have the
`ability to deposit the anti-dandruff active superiorly on the hair or scalp.
`
`Applicants have funher discovered that excellent bioavailability and coverage of the anti-
`dandruff active from a given shampoo compositions can be achieved if the coacervate formed
`between the cationic polymer and the anionic surfactant upon dilution of the shampoo is spreadable
`
`and flowable, rather than elastic in nature. The nature of the coacervate is impacted by the level and
`
`types of cationic polymer present in the shampoo composition.
`It is an object of the present invention to provide shampoo compositions which provide a
`superior combination of anti-dandruff effrcacy and conditioning. It is also an object of the present
`invention to provide a method for cleansing and conditioning the hair. These, and other objects, will
`
`become readily apparent from the detailed description below.
`
`20
`
`25
`
`30
`
`SUMMARY OF THE INVENTION
`
`The present invention relates to shampoo compositions that provide a superior combination
`
`35
`
`of anti-dandruff efficacy and conditioning. These shampoos comprise: (A) from about 5% to about
`
`50Yo,by weight, of an anionic surfactant; (B) from about 0.01% to about l\Yo,by weight, of a non-
`volatile conditioning agent; (C) from about O.lYo to about 4%o, by weight, of an anti-dandruff
`
`3
`
`8
`
`
`
`particulate; (D) from about 0.02Yo to about 5o/o, by weight, of a cationic guar derivative; and (E)
`
`water. The cationic guar derivative has a molecular weight from about 50,000 to about 700,000, and
`
`has a charge density from about 0.05 meq/g to about 1.0 meq/g.
`
`The present invention further relates to a method for providing anti-dandruff efficacy and
`conditioning hair comprising applying to the hair and scalp an amount of the above-described
`composition which is effective to provide such benefits.
`
`l0
`
`l5
`
`20
`
`25
`
`30
`
`35
`
`DETAILED DESCRIPTION OF THE INVENTION
`
`The shampoo compositions of the present invention provide a superior combination of anti-
`
`dandruff efficacy and conditioning. Such anti-dandruff and conditioning shampoo compositions can
`
`comprise, consist of, or consist essentially of the essential elements and limitations of the invention
`described herein, as well as any of the additional or optional ingredients, components or limitations
`
`described herein.
`
`Particularly, these compositions comprise anionic sirfactants, conditioning agents, anti-
`
`dandruff particulates, cationic guars, and water. Upon dilution, the anionic surfactants and cationic
`
`guars form a coacervate. The molecular weight and charge density of the cationic guar will influence
`
`the bioavailability and coverage of the anti-dandruff particulate. This is important for anti-dandruff
`
`effi cacy and conditioning.
`The components, including those which may optionally be added, of the shampoo
`compositions of the present invention, as well as methods for preparation, and methods for use, are
`
`described in detail below.
`
`I. Components
`The anti-dandruff and conditioning shampoo compositions of the present invention
`comprise an anionic surfactant, a conditioning agent, an anti-dandruff particulate, a cationic guar
`
`derivative, and an aqueous carrier. Each ofthese ingredients is described in detail below.
`
`A. Anionic surfactant
`The anti-dandruff and conditioning shampoo compositions of the present invention
`comprise from about 5% to about 50Yo,by weight of the composition, preferably from about 8% to
`
`about 30%, more preferably from about l0% to about 2|o/o,mostpreferably from about l2%oto about
`l8%, of an anionic detersive surfactant component suitable for application to the hair or skin. The
`anionic detersive surfactant is believed to provide cleaning and lather performance to the
`composition. Additionally, the anionic detersive surfactant forms a coacervate, upon aqueous
`dilution, with the cationic polymer component (described below) of the present invention. This
`coacervate is believed to be important in providing the efficacy and conditioning benefits described
`
`herein.
`
`4
`
`9
`
`
`
`:i
`
`The anionic detersive surfactant component can comprise an anionic detersive surfactant, a
`
`zwitterionic or an amphoteric detersive surfactant having an attached moiety that is anionic at the pH
`of the composition, or a combination thereof; preferably an anionic detersive surfactant. Such
`surfactants should be physically and chemically compatible with the essential components described
`herein, and should not otherwise unduly impair product stability, aesthetics or performance.
`Examples of anionic detersive surfactants which may be suitably employed in the shampoo
`compositions herein include, but are not limited to: sulfates, sulfonates, sarcosinates and sarcosine
`
`derivatives.
`
`1. Sulfates
`Preferred anionic detersive surfactants for use in the anti-dandruff and conditioning
`shampoo compositions of the present invention are the alkyl and alkyl ether sulfates. These
`surfactants have the respective formulae ROSO3M and R(C,H.O)*OSO3M, wherein R is alkyl or
`alkenyl from about C, to about C,r, x is an integer having a value from I to 10, and M is a cation
`selected from the group consisting of electropositive covalently bonded moieties (e.g. ammonium),
`alkanolamines (e.9. triethanolamine), monovalent metals (e.g. sodium or potassium), polyvalent
`metal cations (e.g. magnesium and calcium) and mixtures thereof. The cation M should be selected
`such that the anionic detersive surfactant component is water soluble. Solubility of the surfactant
`will depend upon the particular anionic detersive surfactants and cations chosen.
`Preferably, R is from about C, to about C,r, more preferably from about C,o to about C,u,
`most preferably from about C,, to about C,o, in both the alkyl and alkyl ether sulfates. The alkyl
`ether sulfates are typically made as condensation products of ethylene oxide and monohydric
`alcohols from about Cr to about Cr.. The alcohols can be synthetic or they can be derived from fats,
`
`e.g., coconut oil, palm kernel oil, and tallow. Lauryl alcohol and straight chain alcohols derived from
`coconut oil or palm kernel oil are preferred. Such alcohols are reacted with from 0 to about 10,
`preferably from about 2 to about 5, most preferably about 3, moles of ethylene oxide. The resulting
`mixture of molecular species will have, for example, an average of 3 moles of ethylene oxide per
`mole of alcohol, and is sulfated and neutalized.
`Non-limiting examples of alkyl ether sulfates which may be used in the shampoo
`compositions of the present invention include sodium and ammonium salts of coconut alkyl
`triethylene glycol ether sulfate, tallow alkyl triethylene glycol ether sulfate, and tallow alkyl hexa-
`oxyethylene sulfate. Prefened alkyl ether sulfates are those comprising a mixture of individual
`compounds, wherein the compounds in the mixture have an average alkyl chain length from about
`C'o to about C'u and an average degree of ethoxylation of from about I to about 4 moles of ethylene
`
`oxide.
`
`l0
`
`l5
`
`20
`
`25
`
`30
`
`35
`
`Specific examples of preferred alkyl sulfates include, but are not limited to, ammonium
`
`lauryl sulfate, ammonium cocoyl sulfate, potassium lauryl sulfate, potassium cocoyl sulfate, sodium
`lauryl sulfate, sodium cocoyl sulfate, monoethanolamine lauryl sulfate, monoethanolamine cocoyl
`
`f
`
`10
`
`
`
`sulfate, diethanolamine lauryl sulfate, triethanolamine lauryl sulfate, triethylamine lauryl sulfate, and
`
`mixtures thereof. Especially prefered is ammonium lauryl sulfate.
`Specific examples of preferred alkyl ether sulfates include, but are not limited to,
`ammonium laureth sulfate, potassium laureth sulfate, sodium laureth sulfate, monoethanolamine
`
`laureth sulfate, diethanolamine laureth sulfate, triethanolamine laureth sulfate, triethylamine laureth
`
`sulfate, and mixtures thereof. Especially prefened is ammonium laureth sulfate.
`
`Still another class of sulfate surfactants suitable for use in the for use in the anti-dandruff
`
`and conditioning shampoos of the present invention are the sulfated glycerides, an example of which
`
`includes, but is not limited to, lauric monoglyceride sodium sulfate.
`2. Sulfonates
`Also suitable for use in the anti-dandruff and conditioning shampoos of the present
`invention are those anionic detersive surfactants known as olefur sulfonates. As used herein. the term
`
`"olefin sulfonates" refers to compounds which can be produced by the sulfonation of o,-olefins by
`means of uncomplexed sulfirr trioxide, followed by neutralization of the acid reaction mixture in
`
`conditions such that any sulfones which have been formed in the reaction are hydrolyzed to give the
`corresponding hydroxy-alkanesulfonates. The sulfur nioxide can be liquid or gaseous, and is
`usually, but not necessarily, diluted by inert diluents, for example by liquid SOr, chlorinated hydro-
`
`carbons, and the like, when used in the liquid form, or by air, nitrogen, gaseous SOr, and the like,
`when used in the gaseous form. The cr-olefins from which the olefin sulfonates are derived are
`mono-olefins which are from about C,o to about Cro, preferably from about C,, to about C,u.
`Preferably, they are straight chain olefurs. In addition to the true alkene sulfonates and a proportion
`of hydroxy-alkanesulfonates, the olefin sulfonates can contain minor amounts of other materials,
`such as alkene disulfonates depending upon the reaction conditions, proportion of reactants, the
`nature of the starting olefins and impurities in the olefin stock and side reactions during the
`sulfonation process. A non-limiting example of such an a-olefin sulfonate mixture is described in
`
`U.S. Pat. No. 3,332,880, which description is incorporated herein by reference.
`
`Another class of sulfonates suitable for use in the anti-dandruff and conditioning shampoo
`compositions of the present invention are those anionic detersive surfactants known as p-alkyloxy
`
`alkane sulfonates. These surfactants conform to the general Formula (I):
`
`l0
`
`l5
`
`20
`
`25
`
`30
`
`where Rr is a straight chain alkyl group from about Cu to about Cro, Rt is a lower alkyl group from
`about C, to about Cr, preferably C,, and M is a water-soluble cation, as described above.
`
`11
`
`
`
`Still other sulfonates suitable for use in the anti-dandruff and conditioning shampoo
`compositions of the present invention are those anionic detersive surfactants known as alkyl aryl
`sulfonates. Non-limiting examples of alkyl aryl sulfonates include sodium tridecyl benzene sul-
`fonate, sodium dodecyl benzene sulfonate, and mixtures thereof'
`Other suitable sulfonates for use in the anti-dandruff and conditioning shampoos of the
`present invention are the water-soluble salts of organic, sulfuric acid reaction products conforming to
`the formula I Rr-SO3-M ] where Rt is a straight or branched chain, saturated, aliphatic hydrocarbon
`radical from about C, to about Cro, preferably about C,o to about C,r; and M is a cation described
`above. Non-limiting examples of such anionic detersive surfactants are the salts of an organic
`sulfuric acid reaction product of a hydrocarbon of the methane series, including rso-, neo', and
`re-paraffins, and a sulfonating agent, e.g., SO3, H2SO4, obtained according to known sulfonation
`methods. The sulfonation methods may include bleaching and hydrolysis. The salts are preferably
`from about C, to about Cro; more preferably from about C,, to about C,r. heferred are alkali metal
`and ammonium sulfonated Cro to Crs n-paraffins.
`Still other suitable sulfonates for use in the anti-dandruff and conditioning shampoo
`compositions of the present invention are the reaction products of fatty acids, which are esterified
`with isethionic acid, and then neutralized with sodium hydroxide. heferred fatty acids are those
`derived from coconut oil or palm kernel oil. Also suitable are the sodium or potassium salts of fatty
`acid amides of methyl tauride in which the fatty acids are derived from coconut oil or palm kernel
`oil. Other similar anionic surfactants are described in U.S. Pat. No. 2,486,921; U.S. Pat' No'
`2,486,922;and U.S. Pat. No. 2,3g6,278,which descriptions are incorporated herein by reference'
`Other sulfonates suitable for use in the anti-dandruff and conditioning shampoo
`compositions of the present invention are the succinnates, examples of which include, but are not
`limited to, disodium N-octadecylsulfosuccinate, disodium lauryl sulfosuccinate, diammonium lauryl
`sulfosuccinate, tetrasodium N-(1,2-dicarboxyethyl)-N-octadecylsulfosuccinnate, diamyl ester of
`sodium sulfosuccinic acid, dihexyl ester of sodium sulfosuccinic acid, dioctyl esters of sodium
`sulfosuccinic acid, and mixtures thereof.
`3. Sarcosinates and sarcosine derivatives
`Also suitable for use in the anti-dandruff and conditioning shampoos of the present
`invention are those anionic detersive surfactants known as sarcosinates and sarcosine derivatives.
`Sarcosinates are the derivatives of sarcosine and N-methyl glycine, acylated with a fatty acid
`chloride. They conform to the general Formula (II):
`
`l0
`
`l5
`
`20
`
`25
`
`30
`
`ot
`
`lR-c-N- w- c-o-o-x
`
`Ic
`
`H3
`
`{N1r
`
`35
`
`12
`
`
`
`wherein RCO- is a fatty acid radical and wherein X is either hydrogen (acid form) or a cationic
`species, such as Na* or TEA* (salt form). Non-limiting examples of sarcosinates and sarcosine
`derivatives include: sodium lauryl sarcosinate, lauryl sarcosine, cocoyl sarcosine, and mixtures
`
`thereof. A prefened sarcosinate is sodium lauryl sarcosinate.
`
`l0
`
`l5
`
`B. Conditionins agent
`The anti-dandruff and conditioning shampoo compositions of the present invention
`comprise from about 0.01% to about lUYo,by weight of the composition, preferably from about 0.1%
`
`to about 8ol0, more preferably from about 0.1%o to about 5olo, most preferably from about 0.2Yo to
`
`abott 3.5Yo, of a conditioning agent suitable for application to the hair or skin. It is believed that the
`
`conditioning agent provides improved conditioning benefits to the hair, particularly clean hair feel
`
`and wet rinse feel.
`
`The conditioning agent comprises a water insoluble, water dispersible, non-volatile, liquid
`that forms emulsified, liquid particles or are solubilized by the surfactant micelles, in the anionic
`detersive surfactant component (described above). Suitable conditioning agents for use in the
`shampoo composition are those conditioning agents characterized generally as silicones (e.g. silicone
`oils, cationic silicones, silicone gums, high refractive silicones, and silicone resins), organic
`conditioning oils (q.g. hydrocarbon oils, polyolefins, and fatty esters) or combinations thereof, or
`
`those conditioning agents which otherwise form liquid, dispersed, particles in the aqueous surfactant
`
`20
`
`matrix herein. Such conditioning agents should be physically and chemically compatible with the
`
`essential components of the composition, and should not otherwise unduly impair product stability,
`
`aesthetics or performance.
`The concenffation of the conditioning agent in the shampoo composition should be
`sufficient to provide the desired conditioning benefits, and as will be apparent to one of ordinary skill
`in the art. Such concentration can vary with the conditioning agent, the conditioning performance
`desired, the average size of the conditioning agent particles, the type and concentration of other
`
`components, and other like factors.
`l. Silicones
`The conditioning agent of the anti-dandruff and conditioning shampoo compositions of the
`
`present invention is preferably an insoluble silicone conditioning agent. The silicone conditioning
`agent particles may comprise volatile silicone, non-volatile silicone, or combinations thereof.
`Prefened are non-volatile silicone conditioning agents. If volatile silicones are present, it will
`typically be incidental to their use as a solvent or canier for commercially available forms of non-
`volatile silicone materials ingredients, such as silicone gums and resins. The silicone conditioning
`agent particles may comprise a silicone fluid conditioning agent and may also comprise other
`ingredients, such as a silicone resin torimprove silicone fluid deposition efficiency or enhance
`
`25
`
`30
`
`35
`
`13
`
`
`
`glossiness of the hair (especially when high refractive index (e.9. above about 1.46) silicone
`conditioning agents are used (e.g. highly phenylated silicones).
`
`The concentration of the silicone conditioning agent typically ranges from about 0.01% to
`
`about l0%, by weight of the composition, preferably from about 0.1% to about 80/o, more preferably
`from about 0.1%o to about 50lo, most preferably from about 0.2Yo to about 3%. Non-limiting
`examples of suitable silicone conditioning agents, and optional suspending agents for the silicone, are
`
`described in U.S. Reissue Pat. No. 34,584, U.S. Pat. No. 5,104,646, and U.S. Pat. No. 5,106,609,
`
`which descriptions are incorporated herein by reference. The silicone conditioning agents for use in
`
`the anti-dandruff and conditioning shampoo compositions of the present invention preferably have a
`viscosity, as measured at 25"C, from about 20 to about 2,000,000 centistokes ("csk"), more
`preferably from about 1,000 to about 1,800,000 csk, even more preferably from about 50,000 to
`
`about 1,500,000 csk, mostpreferably from about 100,000 to about 1,500,000 csk.
`The dispersed, silicone conditioning agent particles typically have a number average
`particle diameter ranging from about 0.0lpm to about 50pm. !'or small particle application to hair,
`the number average particle diameters typically range from about 0.0lpm to about 4pm, preferably
`
`from about 0.0lpm to about 2pm, more preferably from about 0.0lpm to about 0.5pm. For larger
`
`particle application to hair, the number average particle diameters typically range from about 4pm to
`
`about 50pm, preferably from about 6pm to about 30pm, more preferably from about 9pm to about
`20pm, most preferably from about l2pm to about l8pm. Conditioning agents having an average
`particle size of less than about 5pm may deposit more efficiently on the hair. It is believed that small
`
`size particles of conditioning agent are contained within the coacervate that is formed between the
`
`anionic surfactant component (described above) and the cationic polymer,component (described
`
`below), upon dilution of the shampoo.
`
`Background material on silicones including sections discussing silicone fluids, gums, and
`resins, as well as manufacture of silicones, are found n Encyclopedia of Polymer Science and
`Engineering, vol. 15,2ded., pp 204-308, John Wiley & Sons, Inc. (1989), incorporated herein by
`
`reference.
`i. Silicone oils
`Silicone fluids include silicone oils, which are flowable silicone materials having a
`viscosiry, as measured at 25"C, less than 1,000,000 csk, preferably from about 5 csk to about
`1,000,000 csk, more preferably from about l0 csk to about 100,000 csk. Suitable silicone oils for use
`in the anti-dandruff and conditioning shampoo compositions of the present invention include
`polyalkyl siloxanes, polyaryl siloxanes, polyalkylaryl siloxanes, polyether siloxane copolymers, and
`mixtures thereof. Other insoluble, non-volatile silicone fluids having hair conditioning properties
`
`may also be used.
`Silicone oils include polyalkyl or polyaryl siloxanes which conform to the following
`Formula (III):
`
`10
`
`l5
`
`20
`
`25
`
`30
`
`35
`
`!--
`
`14
`
`
`
`\---
`
`T\c0
`
`.s
`
`9
`
`*
`[*
`lR
`*_I,_ofl,_ol!,_*
`t l|
`tl
`R LR IR
`
`wherein R is aliphatic, preferably alkyl or alkenyl, or aryl, R can be substituted or unsubstituted, and
`x is an integ