(12) United States Patent
`Dunlop et al.
`
`111111
`
`1111111111111111111111111111111111111111111111111111111111111
`US006974569B2
`
`(10) Patent No.:
`(45) Date of Patent:
`
`US 6,974,569 B2
`Dec. 13, 2005
`
`(54) SHAMPOOS PROVIDING A SUPERIOR
`COMBINATION ANTI-DANDRUFF
`EFFICACY AND CONDITION
`
`(75)
`
`Inventors: David Scott Dunlop, Mason, OH (US);
`Roberta Atwood Boyd, Cincinnati, OH
`(US); Susan Marie Guskey,
`Montgomery, OH (US); James Robert
`Schwartz, West Chester, OH (US);
`Anthony Raymond Marchetta, Mason,
`OH (US)
`
`(73) Assignee: The Procter & Gamble Company,
`Cincinnati, OH (US)
`
`( *) Notice:
`
`Subject to any disclaimer, the term of this
`patent is extended or adjusted under 35
`U.S.C. 154(b) by 0 days.
`
`(21) Appl. No.: 09/558,465
`
`(22) Filed:
`
`Apr. 25, 2000
`
`(65)
`
`Prior Publication Data
`
`US 2002/0102228 A1 Aug. 1, 2002
`
`(51)
`
`Related U.S. Application Data
`(60) Provisional application No. 60/132,867, filed on May 3,
`1999.
`Int. Cl? ............................ A61K 7/06; A61K 7!11;
`A61K 7/075
`(52) U.S. Cl. .................. 424/70.1; 424/70.8; 424/70.22;
`424/70.11; 424/70.12; 424/70.13
`(58) Field of Search ............................... 424/70.1, 70.8,
`424/70.22, 70.11, 70.12, 70.13
`
`(56)
`
`References Cited
`U.S. PATENT DOCUMENTS
`
`3,580,853 A
`4,557,928 A
`5,037,818 A
`5,085,857 A
`5,104,645 A *
`RE34,584 E
`5,543,074 A
`5,624,666 A
`5,723,112 A
`5,747,435 A
`5,756,436 A
`5,776,871 A
`5,837,661 A
`5,854,266 A
`5,876,705 A
`5,935,561 A
`5,977,036 A
`5,977,038 A
`6,010,990 A
`
`5/1971
`12/1985
`8/1991
`2/1992
`4/1992
`4/1994
`8/1996
`4/1997
`3/1998
`5/1998
`5/1998
`7/1998
`11/1998
`12/1998
`3/1999
`8/1999
`11/1999
`11/1999
`1!2000
`
`Parr an ........................ 252/152
`Glover . ... .. ... ... ... ... ... .. . 424/70
`Sime .......................... 514/183
`Reid et a!. .................... 424/70
`Cardin eta!.
`Grote eta!. ................ 252/142
`Hague et a!. ............... 510/122
`......... 424/70
`Coffindaffer et a!.
`Bowser et a!. ................ 424/70
`Patel .......................... 510/119
`Royce et a!.
`............... 510/122
`Cothran et a!. . ... ... ... ... 150/122
`Evans et a!. ................ 510/122
`Nelson, Jr ................... 514/345
`Uchiyama et a!. ............ 424/70
`............ 424/70.19
`Inman et a!.
`Guskey ...................... 510/121
`.......... 510/122
`Birtwistle et a!.
`Rousso et a!. .............. 510/124
`
`6,106,816 A
`6,451,300 B1
`6,649,155 B1
`
`8/2000 Hitch en
`9/2002 Dunlop eta!.
`11/2003 Dunlop eta!.
`
`FOREIGN PATENT DOCUMENTS
`
`007704
`EP
`060611
`EP
`093541
`EP
`117135
`EP
`173259
`EP
`497163
`EP
`530974
`EP
`432951
`EP
`800814
`EP
`58-029900
`JP
`05-310540
`JP
`08301724 A2
`JP
`09188614 A
`JP
`10-175827
`JP
`wo 93/08787
`wo
`wo 95/09599
`wo
`wo
`96/29983
`wo 97/26854
`wo
`wo
`97/35542
`wo 98/16189
`wo
`wo 98/18434
`wo
`wo 98/52927
`wo
`wo 99/26585
`wo
`wo
`99/39683
`wo
`99/66886
`* cited by examiner
`
`6/1979
`1!1982
`4/1983
`2/1984
`8/1985
`8/1992
`8/1992
`10/1993
`10/1997
`2/1983
`11/1992
`11/1996
`7/1997
`6/1998
`5/1993
`4/1995
`* 10/1996
`7/1997
`10/1997
`4/1998
`5/1998
`11/1998
`6/1999
`8/1999
`12/1999
`
`............ A61K/7/06
`............ A61K/7/06
`............ A61K/7/06
`............ C11D/3/37
`............ A61K/7/06
`............ A61K/7/06
`............ A61K/7/06
`.......... A61K/7/075
`............ A61K/7/06
`............ A61K/7/06
`A61K/7/075
`
`. ......... A61K/7/075
`............ A61K/7/06
`............ A61K/7/06
`
`............ A61K/7/06
`............ A61K/7/06
`............ A61K/7/06
`............ A61K/7/06
`......... C07D/241!36
`............ A61K/7/00
`............ A61K/7/06
`............ A61K/7/06
`
`Primary Examiner-Thurman K. Page
`Assistant Examiner---Humera N. Sheikh
`(74) Attorney, Agent, or Firm-Linda M. Sivik; Brent M.
`Peebles; Marianne Dressman
`
`(57)
`
`ABSTRACT
`
`Disclosed are shampoo compositions that provide a superior
`combination of anti-dandruff efficacy and conditioning, and
`a method of cleansing and conditioning the hair comprising
`applying to the hair and scalp an amount of said composi(cid:173)
`tions. The anti-dandruff and conditioning shampoos com(cid:173)
`prise: (A) from about 5% to about 50%, by weight, of an
`anionic surfactant; (B) from about 0.01% to about 10%, by
`weight, of a non-volatile conditioning agent; (C) from about
`0.1% to about 4%, by weight, of an anti-dandruff agent; (D)
`from about 0.02% to about 5%, by weight, of at least one
`cationic polymer; and (E) water. The compositions (A) have
`a bioavailability /coverage index value, as defined herein, of
`at least about 1.25; (B) have a first conditioning index value,
`as defined herein, of less than or equal to about 1.0; (C) have
`a second conditioning index value, as defined herein, of at
`least about 1.5; and (D) have a minimal inhibitory concen(cid:173)
`tration index value, as defined herein, of at least about 0.125.
`
`33 Claims, No Drawings
`
`1
`
`

`

`US 6,974,569 B2
`
`1
`SHAMPOOS PROVIDING A SUPERIOR
`COMBINATION ANTI-DANDRUFF
`EFFICACY AND CONDITION
`
`This application claims benefit of 60/132,867 filed May 5
`3, 1999.
`
`TECHNICAL FIELD OF THE INVENTION
`The present invention relates to shampoo compositions
`which provide a superior combination of anti-dandruff effi(cid:173)
`cacy and conditioning. These compositions contain anionic
`surfactants, conditioning agents, anti-dandruff agents, cat(cid:173)
`ionic polymers, and water. These anti-dandruff and condi(cid:173)
`tioning shampoo compositions exhibit (a) at least a certain
`bioavailability/coverage index value, (b) less than or equal
`to a certain first conditioning index value, (c) at least a
`certain second conditioning index value, and (d) at least a
`certain minimal inhibitory concentration index value, as
`defined herein.
`
`2
`ing a coacervate to deposit anti-dandruff actives on the hair
`and scalp. Unfortunately, the use of 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 anti -dandruff efficacy.
`Applicants have now discovered, however, that,
`surprisingly, bioavailability and coverage of the anti-
`10 dandruff active are much more predictive of efficacy than
`deposition of the 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.
`15 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 compo(cid:173)
`sition to provide a superior combination of anti-dandruff
`20 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 supe-
`riorly on the hair or scalp.
`Applicants have found that four requirements must be
`satisfied in order to provide shampoo compositions which
`provide a superior combination of efficacy and conditioning.
`Particularly, (1) bioavailability and coverage of the anti(cid:173)
`dandruff active are important to anti -dandruff efficacy; (2)
`30 comb-ability of wet hair and (3) clean hair feel are important
`to the consumer perception of well-conditioned hair; and ( 4)
`the inherent ability of the anti -dandruff active to inhibit the
`growth of microorganisms has an impact on the anti(cid:173)
`dandruff efficacy as well as overall consumer acceptance of
`35 the shampoo product.
`Whether or not the requisite criteria are met for a given
`shampoo composition depends on a number of aspects of the
`shampoo formulation including, for example, the level and
`type of cationic polymer employed in the composition, the
`type of anti-dandruff agent employed, the amount of anionic
`surfactant employed, the level and type of polyalkylene
`glycol employed, if any, and the rheological characteristics
`of the coacervate.
`It is an object of the present invention to provide shampoo
`compositions, which provide a superior combination of
`anti-dandruff efficacy 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.
`
`25
`
`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 condi(cid:173)
`tioning performance. For example, Pantene® Shampoo Plus
`Pro-Vitamin Conditioner-in-One formulas which contain
`anionic surfactants, a cationic polymer and silicone condi(cid:173)
`tioning agents provide excellent cleaning, conditioning and
`hair feel benefits upon application to hair.
`Anti-dandruff shampoos are also well known in the art
`and are also commercially available. Anti-dandruff sham(cid:173)
`poos typically incorporate an anti-dandruff active and deter(cid:173)
`sive 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 pyridi(cid:173)
`nethione. Soluble anti-dandruff agents, such as
`ketoconazole, are also known in the art.
`Anti-dandruff shampoos which also provide conditioning 40
`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 45
`such as silicone fluids can optionally be incorporated into
`the compositions therein. Head & Shoulders® Dandruff
`Shampoo Plus 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 con(cid:173)
`ditioning can be difficult to achieve.
`For example, one way to achieve excellent conditioning
`benefits is to employ a fairly high level of cationic polymer
`in the shampoo composition. However, the use of high levels
`of cationic polymer can affect the characteristics of the
`coacervate formed between the cationic polymer and the 60
`anionic surfactant in a manner which negatively impacts the
`deposition of the anti-dandruff active on the hair and scalp.
`Thus, it has heretofore been believed that the level of
`cationic polymer had to be balanced to provide the best
`balance of conditioning and anti -dandruff efficacy.
`Also by way of example, it was previously believed that
`excellent anti -dandruff efficacy could be achieved by utiliz-
`
`50
`
`SUMMARY OF THE INVENTION
`The present invention relates to a shampoo composition
`comprising: (A) from about 5% to about 50%, by weight, of
`an anionic surfactant; (B) from about 0.01% to about 10%,
`55 by weight, of a non-volatile conditioning agent; (C) from
`about 0.1% to about 4%, by weight, of an anti-dandruff
`agent; (D) from about 0.02% to about 5%, by weight, of at
`least one cationic polymer; and (E) water. The composition
`(A) has a bioavailability/coverage index value, as defined
`herein, of at least about 1.25; (B) has a first conditioning
`index value, as defined herein, of less than or equal to about
`1.0; (C) has a second conditioning index value, as defined
`herein, of at least about 1.5; and (D) has a minimal inhibitory
`concentration index value, as defined herein, of at least
`65 about 0.125.
`The present invention further relates to a method for
`providing anti-dandruff efficacy and conditioning hair com-
`
`2
`
`

`

`US 6,974,569 B2
`
`5
`
`4
`about 0.125, preferably at least about 0.25, more preferably
`at least about 0.5. This index is indicative of anti-dandruff
`efficacy. Generally, the higher the index value of the
`composition, the better its anti -dandruff efficacy, due to
`increased inherent ability of the anti-dandruff agent to
`inhibit the growth of microorganisms.
`The components, including those which may optionally
`be added, of the shampoo compositions of the present
`invention, as well as methods for preparation, methods for
`10 use are described in detail below. Also, methods for assess(cid:173)
`ing the four indecies are described in detail.
`
`15
`
`3
`prising applying to the hair and scalp an amount of the
`above-described composition which is effective to provide
`such benefits.
`DETAILED DESCRIPTION OF 1HE
`INVENTION
`The shampoo compositions of the present invention pro(cid:173)
`vide 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
`surfactants, conditioning agents, anti-dandruff agents, cat-
`ionic polymers, and water. More particularly, these compo(cid:173)
`sitions exhibit certain characteristics which are measured by
`four indecies, defined herein.
`The shampoo compositions of the present invention have
`a bioavailability/coverage index value of at least about 1.25,
`preferably at least about 1.5, more preferably at least about
`2.0. This index is indicative of anti-dandruff efficacy.
`Generally, the higher the index value of the composition, the
`better its anti-dandruff efficacy, due to more bioavailable
`anti-dandruff agent, increased coverage of anti-dandruff 25
`agent, or both. Applicants have discovered that, surprisingly,
`bioavailability and coverage of the anti -dandruff active are
`much more predictive of efficacy than deposition of the
`active on the hair or scalp. In fact, Applicants have found
`that, in some cases, even when an antidandruff active 30
`deposited very well on the hair and scalp, acceptable anti(cid:173)
`dandruff efficacy was not achieved. Conversely, good anti(cid:173)
`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 35
`scalp.
`Applicants believe that there are a number of ways to
`increase the bioavailability of the anti-dandruff active. For
`example, the composition can be formulated (as hereinafter
`described) such that the anti-dandruff active is present on the 40
`surface of the coacervate (i.e., loosely associated with the
`coacervate) rather than integrated into or encapsulated by
`the coacervate. Another way to increase bioavailability of
`the anti -dandruff active is to formulate the composition (as
`hereinafter described) such that the coacervate is spreadable 45
`or fiowable (rather than elastic) to increase the bioavailabil-
`ity of any anti-dandruff active that is integrated into or
`encapsulated by the coacervate.
`The shampoo compositions of the present invention have
`a first conditioning index value of less than or equal to about 50
`1.0, preferably less than or equal to about 0.96, more
`preferably less than or equal to about 0.94, most preferably
`less than or equal to about 0. 91. This index is indicative of
`conditioning, as realized by consumers of the shampoo
`composition. Generally, the lower the index value of the 55
`composition, the better its conditioning, due to easier to
`comb and less tangled wet hair.
`The shampoo compositions of the present invention have
`a second conditioning index value of at least about 1.5,
`preferably at least about 1.75, more preferably at least about 60
`2.0, still more preferably at least about 2.25, most preferably
`at least about 2.5. This index is indicative of conditioning, as
`realized by consumers of the shampoo composition.
`Generally, the higher the index value of the composition, the
`better its conditioning, due to increased clean hair feel.
`The shampoo compositions of the present invention have
`a minimal inhibitory concentration index value of at least
`
`20
`
`1. Components
`The anti-dandruff and conditioning shampoo composi(cid:173)
`tions of the present invention comprise an anionic
`surfactant, a conditioning agent, an anti-dandruff agent, a
`cationic polymer, and water. Each of these ingredients is
`described in detail below.
`A Anionic Surfactant
`The anti-dandruff and conditioning shampoo composi(cid:173)
`tions of the present invention comprise from about 5% to
`about 50%, by weight of the composition, preferably from
`about 8% to about 30%, more preferably from about 10% to
`about 25%, most preferably from about 12% to about 18%,
`of an anionic detersive surfactant component suitable for
`application to the hair or skin. The anionic detersive surfac-
`tant is believed to provide cleaning and lather performance
`to the composition. Additionally, the anionic detersive sur(cid:173)
`factant forms a coacervate, upon aqueous dilution, with the
`cationic polymer component (described below) of the
`present invention. This coacervate is believed to be impor-
`tant in providing the efficacy and conditioning benefits
`described herein.
`The anionic detersive surfactant component can comprise
`an anionic detersive surfactant, a zwitterionic or an ampho(cid:173)
`teric 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 composi(cid:173)
`tions 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 ROS0 3 M
`and R(C2H4 0)xOS03M, wherein R is alkyl or alkenyl from
`about C8 to about C18, x is an integer having a value from
`1 to 10, and M is a cation selected from the group consisting
`of electropositive covalently bonded moieties (e.g.
`ammonium), alkanolamines (e.g. triethanolamine), monova(cid:173)
`lent 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 C8
`to about C18 , more
`preferably from about c12 to about c16' most preferably
`from about c12 to about c14, in both the alkyl and alkyl ether
`65 sulfates. The alkyl ether sulfates are typically made as
`condensation products of ethylene oxide and monohydric
`alcohols from about C8 to about C24. The alcohols can be
`
`3
`
`

`

`OR2 H
`
`1t+so3M
`
`R
`
`H H
`
`5
`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, 5
`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
`neutralized.
`Non-limiting examples of alkyl ether sulfates which may 10
`be used in the shampoo compositions of the present inven(cid:173)
`tion include sodium and ammonium salts of coconut alkyl
`triethylene glycol ether sulfate, tallow alkyl triethylene
`glycol ether sulfate, and tallow alkyl hexaoxyethylene sul(cid:173)
`fate. Preferred alkyl ether sulfates are those comprising a 15
`mixture of individual compounds, wherein the compounds
`in the mixture have an average alkyl chain length from about
`C10 to about C16 and an average degree of ethoxylation of
`from about 1 to about 4 moles of ethylene oxide.
`Specific examples of preferred alkyl sulfates include, but 20
`are not limited to, ammonium lauryl sulfate, ammonium
`cocoyl sulfate, potassium lauryl sulfate, potassium cocoyl
`sulfate, sodium lauryl sulfate, sodium cocoyl sulfate, mono(cid:173)
`ethanolamine lauryl sulfate, monoethanolamine cocoyl
`sulfate, diethanolamine lauryl sulfate, triethanolamine lauryl 25
`sulfate, triethylamine lauryl sulfate, and mixtures thereof.
`Especially preferred 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, monoet- 30
`hanolamine laureth sulfate, diethanolamine laureth sulfate,
`triethanolamine laureth sulfate, triethylamine laureth sulfate,
`and mixtures thereof. Especially preferred 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 deter(cid:173)
`sive surfactants known as olefin sulfonates. As used herein,
`the term "olefin sulfonates" refers to compounds which can
`be produced by the sulfonation of a-olefins by means of
`uncomplexed sulfur trioxide, followed by neutralization of
`the acid reaction mixture in conditions such that any sul(cid:173)
`fones which have been formed in the reaction are hydro(cid:173)
`lyzed to give the corresponding hydroxy-alkanesulfonates.
`The sulfur trioxide can be liquid or gaseous, and is usually,
`but not necessarily, diluted by inert diluents, for example by
`liquid so2, chlorinated hydrocarbons, and the like, when
`used in the liquid form, or by air, nitrogen, gaseous so2, and
`the like, when used in the gaseous form. The a-olefins from
`which the olefin sulfonates are derived are mono-olefins 55
`Which are from about C10 to about C24, preferably from
`about C12 to about C16 . Preferably, they are straight chain
`olefins. In addition to the true alkene sulfonates and a
`proportion of hydroxy-alkanesulfonates, the olefin sul(cid:173)
`fonates can contain minor amounts of other materials, such 60
`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. 65
`No. 3,332,880, which description is incorporated herein by
`reference.
`
`US 6,974,569 B2
`
`6
`Another class of sulfonates suitable for use in the anti(cid:173)
`dandruff and conditioning shampoo compositions of the
`present invention are those anionic detersive surfactants
`known as ~-alkyloxy alkane sulfonates. These surfactants
`conform to the general Formula (I):
`
`where R1 is a straight chain alkyl group from about C6 to
`about C20 , R2 is a lower alkyl group from about C1 to about
`C3 , preferably C1 , and M is a water-soluble cation, as
`described above.
`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 sulfonate,
`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 prod(cid:173)
`ucts conforming to the formula [R 1-S03-M ] where R 1 is
`a straight or branched chain, saturated, aliphatic hydrocar(cid:173)
`bon radical from about Cg to about c24, preferably about clO
`to about C18 ; 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 iso-, neo-, and
`n-paraffins, and a sulfonating agent, e.g., S03 , H2S04 ,
`obtained according to known sulfonation methods. The
`35 sulfonation methods may include bleaching and hydrolysis.
`The salts are preferably from about C8 to about C24; more
`preferably from about C12 to about C18 . Preferred are alkali
`metal and ammonium sulfonated C10 to C18 n-paraffins.
`Still other suitable sulfonates for use in the anti-dandruff
`40 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. Preferred fatty acids are those derived
`from coconut oil or palm kernel oil. Also suitable are the
`45 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. Nos. 2,486,921; 2,486,922; and 2,396,
`278, which descriptions are incorporated herein by refer-
`50 ence.
`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,
`tetra so di urn
`N- ( 1, 2 -die arb o xye th yl) -N(cid:173)
`octadecylsulfosuccinnate, diamyl ester of sodium sulfosuc(cid:173)
`cinic acid, dihexyl ester of sodium sulfosuccinic acid, dio(cid:173)
`ctyl 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 deter(cid:173)
`sive surfactants known as sarcosinates and sarcosine deriva(cid:173)
`tives. Sarcosinates are the derivatives of sarcosine and
`N-methyl glycine, acylated with a fatty acid chloride. They
`conform to the general Formula (11):
`
`4
`
`

`

`US 6,974,569 B2
`
`7
`
`0
`
`II R-C-N-CH -C-0-0-X
`I
`CH3
`
`2
`
`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 sarco(cid:173)
`sinates and sarcosine derivatives include: sodium lauryl
`sarcosinate, lauryl sarcosine, cocoyl sarcosine, and mixtures
`thereof. A preferred sarcosinate is sodium lauryl sarcosinate.
`B. Conditioning Agent
`The anti-dandruff and conditioning shampoo composi(cid:173)
`tions of the present invention comprise from about 0.01% to
`about 10%, by weight of the composition, preferably from
`about 0.1% to about 8%, more preferably from about 0.1%
`to about 5%, most preferably from about 0.2% to about
`3.5%, 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, particu(cid:173)
`larly 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 (e.g. hydrocarbon oils, polyolefins,
`and fatty esters) or combinations thereof, or those condi(cid:173)
`tioning agents which otherwise form liquid, dispersed, par(cid:173)
`ticles in the aqueous surfactant matrix herein. Such condi(cid:173)
`tioning agents should be physically and chemically
`compatible with the essential components of the
`composition, and should not otherwise unduly impair prod(cid:173)
`uct stability, aesthetics or performance.
`The concentration of the conditioning agent in the sham(cid:173)
`poo composition should be sufficient to provide the desired 40
`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 45
`like factors.
`1. Silicones
`The conditioning agent of the anti-dandruff and condi(cid:173)
`tioning shampoo compositions of the present invention is
`preferably an insoluble silicone conditioning agent. The 50
`silicone conditioning agent particles may comprise volatile
`silicone, non-volatile silicone, or combinations thereof. Pre(cid:173)
`ferred are non-volatile silicone conditioning agents. If vola(cid:173)
`tile silicones are present, it will typically be incidental to
`their use as a solvent or carrier for commercially available 55
`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 to improve silicone fluid deposition efficiency or 60
`enhance glossiness of the hair (especially when high refrac(cid:173)
`tive index (e.g. above about 1.46) silicone conditioning
`agents are used (e.g. highly phenylated silicones).
`The concentration of the silicone conditioning agent typi(cid:173)
`cally ranges from about 0.01% to about 10%, by weight of 65
`the composition, preferably from about 0.1% to about 8%,
`more preferably from about 0.1% to about 5%, most pref-
`
`10
`
`8
`erably from about 0.2% to about 3%. Non-limiting examples
`of suitable silicone conditioning agents, and optional sus(cid:173)
`pending agents for the silicone, are described in U.S. Reis(cid:173)
`sue Pat. No. 34,584, U.S. Pat. Nos. 5,104,646, and 5,106,
`5 609, 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, most preferably from about 100,000 to about
`1,500,000 csk.
`The dispersed, silicone conditioning agent particles typi(cid:173)
`cally have a number average particle diameter ranging from
`15 about 0.01 ,urn to about 5 ,urn. For small particle application
`to hair, the number average particle diameters typically
`range from about 0.01 ,urn to about 4 ,urn, preferably from
`about 0.01 ,urn to about 2 ,urn, more preferably from about
`0.01 ,urn to about 0.5 ,urn. For larger particle application to
`20 hair, the number average particle diameters typically range
`from about 4,um to about 50 ,urn. preferably from about 6 ,urn
`to about 30 ,urn, more preferably from about 9 ,urn to about
`20 ,urn, most preferably from about 12,um to about 18,um.
`Conditioning agents having an average particle size of less
`25 than about 5 ,urn 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 dilu-
`30 tion of the shampoo.
`Background material on silicones including sections dis(cid:173)
`cussing silicone fluids, gums, and resins, as well as manu(cid:173)
`facture of silicones, are found in Encyclopedia of Polymer
`Science and Engineering, vol. 15, 2d ed.,