United States Patent [19J
`Shin et al.
`
`[54] HAIR-CARE COSMETIC COMPOSITIONS
`HAVING DANDRUFF FORMATION(cid:173)
`SUPPRESSING EFFECT
`
`[75]
`
`Inventors: Moon Sam Shin, Suwon; Sang Cho
`Choi, Seongnam; Yong Duk Kwak,
`Taejeon; Seong Hwan Seo, Yongin;
`Han II Jeong, Anyang; Kyung Hee
`Seo, Kangnam-ku, all of Rep. of Korea
`
`[73] Assignee: Pacific Corporation, Seoul, Rep. of
`Korea
`
`[21] Appl. No.: 861,730
`
`[22] Filed:
`
`May 22, 1997
`
`[30]
`
`Foreign Application Priority Data
`
`Jan. 27, 1997
`Jan. 27, 1997
`Mar. 22, 1997
`May 7, 1997
`
`[KR]
`[KR]
`[KR]
`[KR]
`
`Rep. of Korea .................... 1997-2207
`Rep. of Korea .................... 1997-2208
`Rep. of Korea .................... 1997-9984
`Rep. of Korea .................. 1997-17380
`
`Int. Cl.6
`......................... A61K 31/27; A61K 31!555
`[51]
`[52] U.S. Cl. .......................... 514/478; 514/479; 514/188;
`514/852
`
`111111
`
`1111111111111111111111111111111111111111111111111111111111111
`US005886031A
`[11] Patent Number:
`[45] Date of Patent:
`
`5,886,031
`Mar. 23, 1999
`
`[58] Field of Search ..................................... 514/478, 479,
`514/188, 852
`
`[56]
`
`References Cited
`
`U.S. PATENT DOCUMENTS
`
`3,961,054
`4,844,891
`5,451,564
`5,739,093
`
`6/1976 Turia et a!. ............................. 424/245
`7/1989 Risen eta!. ............................ 424/76.4
`9/1995 Austin et a!. ........................... 504/221
`4/1998 Gutierrez et a!. . ... .... ... ... ... ... ... 510/276
`
`OTHER PUBLICATIONS
`
`CA 124: 324991, Schwartz Apr. 10, 1996.
`
`Primary Examiner-Rebecca Cook
`Attorney, Agent, or Firm-Foley & Lardner
`
`[57]
`
`ABSTRACT
`
`Disclosed herein is hair-care cosmetic compositions com(cid:173)
`prising iodopropynyl butylcarbamate and/or a solution of
`zinc pyrithione in N-acyl ethylenediamine triacetate.
`
`7 Claims, No Drawings
`
`1
`
`

`

`5,886,031
`
`1
`HAIR-CARE COSMETIC COMPOSITIONS
`HAVING DANDRUFF FORMATION(cid:173)
`SUPPRESSING EFFECT
`
`BACKGROUND OF THE INVENTION
`
`10
`
`2
`Pityrosporum ovlae. As a result thereof, they found unex(cid:173)
`pectedly that the Minimum Inhibitition Concentration
`(MIC) of iodopropynl butylcarbamate against Pityrosporum
`ovlae is very low. This compound, iodopropynl butylcar-
`5 bamate has been used as a general preservative due to its
`sterilizing effect against bacteria and yeast. The inventors
`expected this compound to be available as an antibacterial
`agent and tried to apply it to hair-care products, for example
`shampoo. They found that the resulting hair-care cosmetic
`compositions showed an excellent suppressing effect on
`dandruff-formation and itch.
`Further, they reviewed the synergistic effect for the com(cid:173)
`binations of iodopropynl butylcarbamate with zinc
`pyrithione, the latter being a typical antibacterial compound
`against Pityrosporum ovlae. A hair-care composition con-
`15 taining iodopropynl butylcarbamate and zinc pyrithione,
`although it is slightly unstable due to low solubility of zinc
`pyrithione in water, showed synergistic effects in antibacte(cid:173)
`rial activity against Pityrosporum ovlae and thereby dan(cid:173)
`druff reduction and itch-suppressing effect.
`Furthermore, in order to solve the above problem asso(cid:173)
`ciated with low solubility of zinc pyrithione in water, they
`studied the mechanism of dissolution of zinc pyrithione in
`water.
`Zinc pyrithione has a spherical shape and a particle size
`of 0.3-10 ,urn. And it is substantially insoluble in water
`(10-20 ppm), ethanol (310 ppm) and most common organic
`solvents such as ethylene glycol, diethyl ether and isopro(cid:173)
`panol.
`Accordingly, it has been found difficult to formulate
`suitable cosmetic compositions containing zinc pyrithione in
`a dissolved form. In general, it has been accepted that such
`a low solubility of zinc pyrithione is due to a heavy metal,
`zinc, contained in the molecule. In other words, the zinc
`35 pyrithione-dissolution needs a ligand capable of coordinate
`bonding with zinc contained in zinc pyrithione. As an
`appropriate example, amines such as diethanolamine and
`EDTA (ethylenediaminetetraacetic acid) have been
`employed. These amines have unshared electron pairs
`40 capable of coordinate bonding with zinc. (See U.S. Pat. No.
`3,785,985 or U.S. Pat. No. 3,940,482).
`These amines have a pH of 9 or higher showing that they
`are strongly alkaline. Consequently, after dissolving zinc
`pyrithione, acid, for example citric acid, should be added
`45 into the composition so as to adjust the pH value thereof to
`neutral. However, by this pH change, the dissolved zinc
`pyrithione forms insoluble precipitates and the resulting
`composition becomes unstable. Further, these amines emit a
`strong, unpleasant odor, for example, an ammonia-like
`50 smell.
`Under this circumstance, the present inventors have done
`research to provide a solution for the above problems
`associated with the low solubility of zinc pyrithione, such as
`instability of composition caused by precipitation of zinc
`55 pyrithione, and to find new materials having unshared elec(cid:173)
`tron pairs capable of coordinate bonding with zinc contained
`in zinc pyrithione and maintaining a neural pH. As a result,
`they found N-acyl ethylenediamine triacetate to meet the
`above qualification.
`Iodopropynyl butylcarbamate used in the hair-care cos(cid:173)
`metic composition according to invention has the formula (I)
`
`1. Filed of the Invention
`The present invention relates to hair-care cosmetic com(cid:173)
`positions having dandruff formation-suppressing effect.
`More particularly, it relates to hair-care cosmetic composi(cid:173)
`tions containing iodopropynyl butylcarbamate and/or a solu(cid:173)
`tion of zinc pyrithione solubilized by a chelator such as
`N-acyl ethylenediamine triacetate.
`2. Description of the Prior Art
`In general, "dandruff" is a keratin-like mass resulting
`from coagulation of dead cells shed from scalp and seba(cid:173)
`ceous secretion of scalp. Dandruff undergoes a change of its
`color into reddish gradually and forms a clear boundary
`from normal skin. Occasionally, it causes a skin disease with
`accompanying itching and inflammation.
`It has been known, though not clearly, that such dandruff
`may be caused by a hormone imbalance, a nutrition
`imbalance, nervous stresses, biochemical changes in the
`epidermal tissue resulting from an excessive multiplication
`of scalp epidermal cells, growths of microorganisms on the 25
`head and activity increase thereof, and inflammations due to
`air pollutions.
`Particularly, Pityrosporum ovlae, which is a parasite on
`dirty scalp, has been widely recognized as a main cause of
`dandruff formation. Multiplication and activity increase of 30
`this dandruff-causing microorganism make dandruff forma(cid:173)
`tion and itches more severe.
`Hence, for the hair-care cosmetics for treatment and
`prevention of dandruff and itching, it is essential to incor(cid:173)
`porate ingredients capable of suppressing multiplication and
`activity of the Pityrosporum ovlae effectively and returning
`abnormal metabolism of the epidermal scalp cells to normal
`condition.
`
`20
`
`SUMMARY OF THE INVENTION
`
`Thus, an object of the invention is to provide hair-care
`cosmetic compositions having an antibacterial action against
`dandruff -causing microorganisms.
`This and other objects will be apparent to those of
`ordinary skill in the art from the following disclosure.
`One object of the invention has been achieved by pro(cid:173)
`viding a hair-care cosmetic composition containing iodopro(cid:173)
`pynyl butylcarbamate, as an active ingredient.
`In another embodiment of the invention provides a hair(cid:173)
`care cosmetic composition containing iodopropynyl butyl(cid:173)
`carbamate and zinc pyrithione.
`A preferred embodiment of the invention provides a
`hair-care cosmetic composition containing iodopropynyl
`butylcarbamate and a solution of zinc pyrithione solubilized
`N-acyl ethylenediamine triacetate.
`Yet another embodiment of the invention provides a
`hair-care cosmetic composition containing a solution of zinc
`pyrithione in N-acyl ethylenediamine triacetate.
`
`DETAILED DESCRIPTION OF THE
`INVENTION
`
`60
`
`The present invention will be described in detail herein(cid:173)
`after.
`The present inventors have searched for materials having
`antibacterial activity against the dandruff-forming strain of
`
`65
`
`0
`II
`l-C=C-CHz-OC-NH-(CHz),-CH,
`
`(I)
`
`The various methods for preparing iodopropynyl butyl(cid:173)
`carbamate were described in detail in U.S. Pat. No. 4,259,
`
`2
`
`

`

`5,886,031
`
`4
`taacetic acid, nitrolotriacetic acid, cyclohexanediamine tet(cid:173)
`raacetic acid, triethanolamineethylenediamine tetraacetic
`acid, ethylenetriamine pentaacetic acid,
`tetraethylenetriamine, ethylenediamine, diethylenetriamine
`5 and their salts. The chelating agent(s) may be incorporated
`in an amount of 0.001-10% by weight based on total weight
`of the composition.
`More specially, when the composition comprises zinc
`pyrithione, it is more advantageous that zinc pyrithione may
`be incorporated in a solution form obtained by dissolving
`zinc pyrithione with N-acyl ethylenediamine triacetate.
`N-acyl ethylenediamine triacetate(hereinafter referred to as
`N-acyl-EDTA) a chelating surfactant which may be synthe(cid:173)
`sized chemically from EDTA and acyl group-containing
`surfactant (Crudden J. 1. and et al, Inform, Vol. 6, No. 6,
`October 1995). It can be represented by formula (lEI) and
`has, in the molecule, EDTA-structure as well as a surfactant-
`structure:
`
`-OOC-H2C
`\
`I
`O=C-(CHz)nCH,
`
`I
`N-CHz-CHz-N
`\
`
`CH2 -COO-
`
`CHz-COO-
`
`3
`350, U.S. Pat. No. 4,841,088, U.S. Pat. No. 5,321,151 and
`U.S. Pat. No. 5,326,899. And it has been applied as a
`preservative for wood materials (see U.S. Pat. No. 4,323,602
`and U.S. Pat. No. 4,977,186).
`The present inventors revealed in the first place that
`iodopropynyl butylcarbamate exhibits an antibacterial
`action against Pityrosporim ovlae and found its action to be
`very strong. Furthermore, they reviewed its applicability to
`formulate hair-care products.
`Iodopropynyl butylcarbamate has a low solubility in 10
`water, but good solubility in ionic or non-ionic surfactants.
`Specially, it shows a high solubility in alcohols or glycol
`derivatives. Based on this fact, they concluded that iodopro(cid:173)
`pynyl butylcarbamate can be applied to and formulated into
`hair-care products. Also, iodopropynyl butylcarbamate is 15
`very stable at a temperature of 70°-80° C. and pH 4-10.
`And, comparing with zinc pyrithione, it is very advanta(cid:173)
`geous over zinc pyrithione in the light of safety and toxicity.
`It has an Acute Oral LD50(rats) of 1470 mg/kg, while zinc
`pyrithione has Acute Oral LD50(rats) of 354 mg/kg. Based 20
`on these facts, the hair-care composition according to the
`present invention may comprise iodopropynyl butylcarbam-
`ate in an amount of 0.001-20% by weight, and preferably of
`0.001-10% by weight based on total weight of the compo(cid:173)
`sition.
`In order to increase adsorption of iodopropynyl butylcar(cid:173)
`bamate to the scalp, the composition may further contain one
`or more adsorption-accelerating agents selected from guar
`hydroxypropyl trimonium chloride, polyquaternium-7,
`polyquaternium-10, and urea, in an amount of 0.001-10%
`by weight based on total weight of the composition.
`Further, zinc pyrithione(zinc salt of l-hydroxy-2(1H)
`pyridinethione) incorporated in the present composition is
`very effective as a dandruff controlling agent represented by
`tile formula (II):
`
`25 wherein, n is an integer from 10 to 18, inclusive.
`N-Acyl-EDTA has unshared electron pairs capable of
`coordinate bonding with zinc contained in zinc pyrithione
`and maintain neutral in itself. It shows foaming and cleans(cid:173)
`ing actions as well as serves as a chelating agent which
`30 blocks metal.
`Special examples of N-Acyl-EDTA are sodium lauroyl
`ethylenediamine triacetate, sodium myristoyl ethylenedi(cid:173)
`amine triacetate, sodium palmitoyl ethylenediamine
`triacetate, sodium stearoyl ethylenediamine triacetate or
`35 sodium cocoyl ethylenediamine triacetate. The N-acyl(cid:173)
`EDTA chelating surfactant may be incorporated in an
`amount of 0.01-20% by weight based on total weight of the
`composition.
`Zinc pyrithione can be dissolved by forming coordinate
`40 bonds with N-acyl-EDTA. Zinc pyrithione dissolved has a
`particle size of 0.0001-0.001 ,urn. Accordingly, an unit
`surface area of zinc pyrithione increases and amount to be
`adsorbed to the skin increases. Further, because its particle
`size is significantly small, its penetration through the skin
`45 barrier increases. In experiments using Adhesive Scotch
`Tape Stripping Method to determine the adsorption into the
`scalp, in case of the dissolved zinc pyrithione, zinc
`pyrithione was detected at all of the 1st through 5th
`strippings, while the insoluble zinc pyrithione was not
`50 detected from 2nd stripping. Due to such increased adsorp(cid:173)
`tion and penetration, a composition containing zinc
`pyrithione solution exhibits an increased antidandruff effect.
`The hair-care compositions according to the present
`invention may be formulated into, for example, shampoos,
`55 rinses, hair-conditioners, hair-tonics, hair-treatment creams
`and lotions, and the like. Each composition of these formu(cid:173)
`lations may, if necessary, contain appropriate vehicles and
`various additives. The kind and amount of these ingredients
`are not critical and can be selected appropriately and easily
`60 by those of ordinary skill in the art.
`Following description will be given as to these cosmetic
`bases and additives, as an example of shampoo.
`Shampoos may contain synthetic surfactants,
`preservatives, thickeners and viscosity controllers, pH
`65 adjusters, perfumes, dyes, hair conditioning components and
`distilled water. Suitable synthetic surfactants may be
`selected from the group consisting of anionic, amphoteric,
`
`(II)
`
`@
`~
`
`N
`
`0
`
`s
`
`I
`~ Zn
`
`I
`s
`
`~ 0
`
`N
`
`t
`'@
`
`It has a spherical shape and a particle size of 0.3-10 ,urn.
`Its solubility in water at 25° C. is only about 15 ppm.
`According to the present invention, for the purpose of
`attaining a synergistic effect, the zinc pyrithione may be
`incorporated into hair-care cosmetic compositions in an
`amount of 0.001-5% by weight based on total weight of the
`composition.
`In order to increase solubility of zinc pyritione, the
`composition according to the present invention may com(cid:173)
`prise one or more conventional chelating agents. Examples
`thereof may include, but are not limited to, EDTA
`(ethylenediamine tetraacetic acid), diethylenetriamine pen-
`
`3
`
`

`

`5,886,031
`
`5
`nonionic and cationic surfactants, and may be incorporated
`in amount of 10-70% by weight, preferably 10-30% by
`weight.
`Examples of suitable anionic surfactants may include
`alkyl or alkylether sulfates represented by formula (IV):
`
`5
`
`CHzCHzOH
`I
`R4CON
`I
`(CHzCHzO)nH
`
`6
`
`(VIII)
`
`(IV)
`
`wherein, R is an alkyl group having 10-22 carbon atoms, n
`is 0 or an integer of 1-4 inclusive and M is water-soluble
`cation such as ammonium, sodium and triethanolamine.
`Preferable examples are alkyl or alkylether sulfates wherein
`R is an alkyl group having 12-16 carbon atoms. More
`particularly, it may be examplified by sodium lauryl sulfate,
`ammonium lauryl sulfate, triethanolamine lauryl sulfate,
`polyoxyethylene sodium lauryl sulfate, or polyoxyethylene
`ammonium lauryl sulfate.
`Examples of suitable amphoteric surfactants may include
`alkyl betaines and alkyl amidopropyl betaines represented
`by formulae (V) and (VI), respectively
`
`(V)
`
`wherein, R1 is an alkyl group having 8-18 carbon atoms, R2
`and R3 are same or different, an alkyl group having 1-3
`carbon atoms, and R4 CO is alkoxy group having 8-16
`10 carbon atoms, and n is 0 or 1 inclusive. More particularly, it
`may be examplified by lauryl diethylamine oxide, alkyl
`dimethylamine oxide derived from coconut oil, diethanola(cid:173)
`mide of lauric acid, diethanolamide of coconut fatty acid and
`monoethanolamide of coconut fatty acid.
`
`15
`
`The above-mentioned surfactants may be incorporated
`singly or as mixtures thereof.
`
`The hair-care cosmetic compositions according to the
`20 present invention can be used in a conventional manner and
`how-often can be determined depending on the skin condi(cid:173)
`tion or tastes of the user.
`
`CH,
`I
`Rr-N+-CHzC00-
`1
`CH,
`
`CH,
`I
`RzCO- NH(CHz)3- N+ -CHzC00-
`1
`CH,
`
`(VI) 25
`
`PREFERRED EMBODIMENTS OF THE
`INVENTION
`
`wherein, R is an alkyl group having 8-18 carbon atoms and
`R2 CO is an alkoxy group having 8-18 carbon atoms. More
`particularly, it may be examplified by cocodimethyl car-
`
`The present invention will be illustrated in more detail by
`30 way of the following Examples. The following Examples are
`merely illustrative and it should be understood that the
`present invention is not limited to these Examples.
`
`<Examples 1-8 and Comparative Examples 1-2>
`Sham oo
`
`C. Examples
`
`Exam les
`
`Ingredients
`
`2
`
`2
`
`3
`
`4
`
`5
`
`7
`
`8
`
`1. Polyoxyethylene lauryl ether
`sodium sulfate (26%)
`2. Sodium lauryl sulfate (28%)
`3. Laury! diethanol amide
`4. Propylene glycol
`5. Methyl p-hydroxy benzoate
`6. Pigment
`7. Perfume
`8. Citric acid
`9.
`Iodopropynyl butylcarbamate
`10. Polyquaternium-7
`11. Zinc pyrithione (48% of suspension)
`12. Zinc pyrithione (powder)
`13. Sodium lauroyl
`ethylenediamine triacetate
`14. EDTA-2Na
`15. Distilled water
`
`30.0
`
`30.0
`
`30.0
`
`30.0
`
`30.0
`
`30.0
`
`30.0
`
`30.0
`
`30.0
`
`30.0
`
`15.0
`4.5
`0.5
`0.2
`q.s
`q.s
`q.s
`
`15.0
`4.5
`0.5
`0.2
`q.s
`q.s
`q.s
`
`1.0
`
`15.0
`4.5
`0.5
`0.2
`q.s
`q.s
`q.s
`1.0
`
`15.0
`4.5
`0.5
`0.2
`q.s
`q.s
`q.s
`1.0
`0.5
`
`15.0
`4.5
`0.5
`0.2
`q.s
`q.s
`q.s
`1.0
`
`1.0
`
`15.0
`4.5
`0.5
`0.2
`q.s
`q.s
`q.s
`0.3
`
`0.3
`1.5
`
`1.5
`
`1.5
`
`1.5
`to 100
`
`15.0
`4.5
`0.5
`0.2
`q.s
`q.s
`q.s
`0.5
`0.5
`
`0.5
`2.5
`
`1.5
`
`15.0
`4.5
`0.5
`0.2
`q.s
`q.s
`q.s
`1.0
`
`15.0
`4.5
`0.5
`0.2
`q.s
`q.s
`q.s
`
`1.0
`5.0
`
`1.0
`5.0
`
`15.0
`4.5
`0.5
`0.2
`q.s
`q.s
`q.s
`
`1.0
`5.0
`
`0.5
`
`boxymethyl betaine, lauryldimethyl carboxymethyl betaine,
`lauryldimethyl a-carboxyethyl betaine, cetyldimethyl car(cid:173)
`boxymethyl betaine, and cocoamindopropyl betaine.
`
`<Experimental Example 1>
`
`Antibacterial action
`
`Examples of suitable nonionic surfactants may include
`alkanolamides and alkylamineoxides represented by formu(cid:173)
`lae (VII) and (VIII), respectively:
`
`(VII)
`
`60
`
`The culture of the test microorganisms was streaked onto
`agar plates containing various concentrations of the sham(cid:173)
`poos prepared in Examples and Comparative Examples, and
`then were cultivated under an aerobic condition for 2 days.
`Growth of the microorganism was observed and MIC
`65 (Minimum Inhibition Concentration) against the test micro(cid:173)
`organism was determined. The results are summarized in
`Table 1.
`
`4
`
`

`

`5,886,031
`
`7
`
`1. Test microorganism
`Pityrosporum ovlae ATCC 12087
`2. Culture medium
`Blood agar medium(Blood agar base +5% final concen(cid:173)
`tration of blood), BHI agar
`
`8
`Comparative Examples, these shampoos were applied to 10
`Groups each consisting of 8 males aged 19 to 45 years, for
`one month.
`Before this test, they washed hair with the conventional
`shampoo, and dandruff accumulated for 3 days were gath-
`
`TABLE 1
`
`MIC (ug/ml)
`
`C. Examples
`
`Examples
`
`2
`
`2
`
`3
`
`4
`
`5
`
`7
`
`8
`
`Pityrospontm ovlae
`
`>10000
`
`5.87
`
`1.08
`
`0.89
`
`0.045
`
`2.14
`
`0.22
`
`0.025
`
`1.88
`
`0.85
`
`<Experimental Example 2>
`
`Inhibition of growth of P. ovlae
`
`20
`
`This test was performed using Skin Disc Diffusion
`Method. First, the culture of the test microorganism
`(Pityrosporum ovlae ATCC 12087) was streaked onto agar
`plates and then were cultivated under an aerobic condition at
`a temperature of 37° C. for 2 days. After skin discs were 25
`sterilized with 70% of ethanol, it was treated with 1!10-
`dilution of the shampoos prepared in Examples and Com(cid:173)
`parative Examples, and then washed with distilled water.
`Skin discs thus treated were placed onto the above agar
`plates. After allowing to stand for 48 hours at a temperature 30
`of 37° C., inhibition zones were measured. The inhibition
`zone was defined as a clear circular zone where the test
`microorganism in the agar plate died by inhibition of the
`material(shampoo dilution) treated on the skin disc. This
`measurement was repeated 3 times and averaged. The values 35
`in Table 2 are the difference between the radius of the
`inhibition zone and the radius of the skin disc.
`
`ered and weighed. In turn, each group washed hair with the
`shampoo of Example or of C. Example every 3 days for one
`month, and thereafter, dandruff accumulated for 3 days was
`collected and weighed. At this time, the accumulated dan(cid:173)
`druff was collected from the scalp using vacuum suction
`apparatus. Dandruff-reduction was determined by following
`formula:
`
`Dandruff formation-reduction(%)~{ (weight(mg) of dandruff before
`test)-(weight(g) of dandruff after 1 month)}+{weight(mg) of
`dandruff before test }x100
`
`TABLE 2
`
`Mean Inhibition Zones (mm)
`
`C. Examples
`
`Examples
`
`2
`
`2
`
`3
`
`4
`
`5
`
`7
`
`8
`
`Inhibition Zones
`(mm)
`
`0.00
`
`10.88
`
`18.55
`
`20.63
`
`30.79
`
`27.4
`
`30.46
`
`38.59
`
`15.65
`
`17.66
`
`<Experimental Example 3>
`
`50
`
`Dandruff formation-reducing action
`
`In order to evaluate and compare dandruff formation(cid:173)
`reducing action of the shampoos prepared in Examples and
`
`TABLE 3
`
`Dandruff formation-reducing effect (%)
`
`C. Examples
`
`Examples
`
`2
`
`2
`
`3
`
`4
`
`5
`
`7
`
`8
`
`Dandruff-reduction
`(%)
`
`1.03
`
`45.8
`
`59.8
`
`65.3
`
`93.3
`
`57.8
`
`73.5
`
`97.8
`
`73.5
`
`90.7
`
`5
`
`

`

`5,886,031
`
`9
`As shown in Tables 1 to 3, shampoos containing iodopro(cid:173)
`pynyl butylcarbamate(Example 1) were more effective in
`inhibiting the growth of P. ovlae and in suppressing the
`formation of dandruff, compared with shampoo containing
`the dispersed zinc pyrithione(C. Example 2).
`Also, shampoo containing the dissolved zinc pyrithione
`(Example 7) was more effective in inhibiting growth of P.
`ovlae and in suppressing the formation of dandruff, com(cid:173)
`pared with shampoo containing the dispersed zinc pyrithione
`(C. Example 2). This may be in that the dissolved zinc 10
`pyrithione exists in the form of molecule, while the dis(cid:173)
`persed zinc pyrithione exists in the form of particle.
`
`10
`2. A method of anti-dandruff treatment, comprising
`administering to a person in need thereof an effective
`amount of an anti-dandruff composition having an antibac(cid:173)
`terial action against dandruff-causing microorganism Pity-
`5 rosporum ovlae, comprising iodopropynyl butyl carbamate
`represented by formula (I) in an amount of 0.3-20% by
`weight based on the total weight of the composition:
`
`0
`II
`I-C=C-CHz-OC-NH-(CHz),-CH,
`
`(I)
`
`<Experimental Example 4>
`
`Stability of the composition
`
`In order to examine stability of the shampoos prepared in
`Examples and C. Examples, these shampoos were stored at
`0° C. for 3 months and at 25° C. for 6 months, and
`precipitation was observed. The results are shown in Table 20
`4.
`
`and one or more adsorption-accelerating agents selected
`from the group consisting of guar hydroxypropyl trimonium
`15 chloride, polyquaternium-10 and urea, in an amount of
`0.001-10% by weight based on the total weight of the
`composition.
`
`3. The method claimed in claim 2, which further com(cid:173)
`prises zinc pyrithione in an amount of 0.001-5% by weight
`based on total weight of the composition.
`
`TABLE 4
`
`C. Example
`
`Examples
`
`2
`
`0
`@
`
`3
`
`7
`
`X
`
`X
`
`X
`
`X
`
`8
`
`X
`
`X
`
`0° C., 3 months
`25° C., 6 months
`
`x
`x
`
`Note)
`@: Serious precipitation
`o: Slight precipitation
`x: No precipitation
`
`4. The method claimed in claim 3, which further com(cid:173)
`prises N-acyl ethylenediamine triacetate represented by for-
`25 mula (III) in an amount of 0.01-20% by weight based on
`total weight of the composition:
`
`30
`
`-OOC-H2C
`\
`I
`O=C-(CHz)nCH,
`
`I
`N-CHz-CHz-N
`\
`
`CH2 -00C-
`
`(III)
`
`CHz-OOC-
`
`As shown in Table 4, the precipitates formed in shampoo
`of C. Example 2 may be that of zinc pyrithione by pH 35
`change. That is to say, zinc pyrithione dissolved or dispersed
`using the alkali may be precipitated by adding citric acid.
`What is claimed is:
`1. A hair-care cosmetic composition having an antibacte(cid:173)
`rial action against dandruff-causing microorganisms, con(cid:173)
`sisting essentially of iodopropynyl butyl carbamate repre(cid:173)
`sented by formula (I) in an amount of 0.3-20% by weight
`based on the total weight of the composition:
`
`40
`
`0
`II
`I-C=C-CHz-OC-NH-(CHz),-CH,
`
`(I) 45
`
`wherein, n is an integer from 10 to 18.
`
`5. The method claimed in claim 4, wherein said N-acyl
`ethylenediamine triacetate is one or more selected from the
`group consisting of sodium lauroyl ethylenediamine
`triacetate, sodium myristoyl ethylenediamine triacetate,
`sodium palmitoyl ethylenediamine triacetate, sodium
`stearoyl ethylenediamine triacetate and sodium cocoyl eth(cid:173)
`ylenediamine triacetate.
`
`6. The method claimed in claim 3, which further com(cid:173)
`prises one or more chelating agents selected from the group
`consisting of ethylenediamine, tetraacetic acid, diethylen(cid:173)
`etriamine pentaacetic acid, nitrilotriacetic acid, cyclohex(cid:173)
`anediamine tetraacetic acid, triethanolamineethylenedi(cid:173)
`amine tetraacetic acid, ethylenetriamine pentaacetic acid,
`50 tetraethylenetriamine, ethylenediamine and diethyltriamine
`or a salt thereof, in an amount of 0.001-10% by weight
`based upon the weight of the composition.
`
`one or more adsorption-accelerating agents selected from
`the group consisting of guar hydroxypropyl trimonium
`chloride, polyquaternium-10 and urea, in an amount of
`0.001-10% by weight based on the total weight of the
`compositions;
`zinc pyrithione in an amount of 0.001-5% by weight
`based on the total weight of the composition;
`N-acyl ethylenediamine triacetate represented by formula 55
`(III) in an amount of 0.01-20% by weight based on the
`total weight of the composition:
`
`-OOC-H2C
`\
`I
`O=C-(CHz)nCH,
`
`I
`N-CHz-CHz-N
`\
`
`CH2 -00C-
`
`(III)
`
`CHz-OOC-
`
`wherein n is an integer from 10 to 18; and one or more
`chelating agents.
`
`7. The method claimed in claim 4, which further com(cid:173)
`prises one or more chelating agents selected from the group
`consisting of ethylenediamine, tetraacetic acid, diethylen(cid:173)
`etriamine pentaacetic acid, nitrilotriacetic acid, cyclohex(cid:173)
`anediamine tetraacetic acid, triethanolamineethylenedi(cid:173)
`amine tetraacetic acid, ethylenetriamine pentaacetic acid,
`60 tetraethylenetriamine, ethylenediamine and diethyltriamine
`or a salt thereof, in an amount of 0.001-10% by weight
`based upon the weight of the composition.
`
`* * * * *
`
`6
`
`