US3236733A - Method of combatting dandruff with pyridinethiones metal salts detergent compositions - Google Patents

Method of combatting dandruff with pyridinethiones metal salts detergent compositions Download PDF

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US3236733A
US3236733A US44485865A US3236733A US 3236733 A US3236733 A US 3236733A US 44485865 A US44485865 A US 44485865A US 3236733 A US3236733 A US 3236733A
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dandruff
pyridinethione
detergent
shampoo
compositions
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Kenneth S Karsten
Wilbur S Taylor
John J Parran
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Procter and Gamble Co
R T Vanderbilt Co Inc
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Procter and Gamble Co
R T Vanderbilt Co Inc
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/02Preparations for cleaning the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4933Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having sulfur as an exocyclic substituent, e.g. pyridinethione
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/006Antidandruff preparations
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S424/00Drug, bio-affecting and body treating compositions
    • Y10S424/04Dandruff
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S514/00Drug, bio-affecting and body treating compositions
    • Y10S514/852Dandruff

Description

United States Patent 3 236 733 METHOD or coMBAiTriNG DANDRUFF WITH PYRIDINETHKONES METAL SALTS DETERGENT COMPOSITIONS Kenneth S. Karsten, Westport, and Wilbur S. Taylor,

Norwalk, Conn, and John J. Parran, Springfield T ownship, Hamilton County, Ohio; said Karsten and said Taylor assignors to R. T. Vanderbilt Company, Inc.,

New York, N.Y., a corporation of New York, and said Parran assignor to The Procter & Gamble Company,

Cincinnati, Ohio, a corporation of Ohio No Drawing. Original application Sept. 5, 1963, Ser. No.

306,684. Divided and this application Apr. 1, 1965,

Ser. No. 444,858

12 Claims. (Cl. 16737) The present invention is a divisional application of application Serial No. 306,684, filed September 5, 1963. Application Serial No. 306,684 is a continuation-impart of application Serial No. 85,005, filed January 26, 1961, and now abandoned. Application Serial No. 85,005 is a continuation-impart of copendin-g application Serial No. 741,- 994, filed June 16, 1958, and now abandoned.

The present invention relates to a novel shampoo composition possessing remarkable anti-dandrufi' effectiveness. The invention also relates to germicidal detergent compo'si. tions. The compositions contemplated by this invention depend upon the presence of 1-hydroXy-2-pyridinethione, salts and esters thereof, and related compounds such as 2,2'-dithiopyridine-1,1-dioxide.

Dandruff is a common affliction most usually associated with the human scalp area. It is recognized that skin normally 'sloughs off the skin surfaces of the human body. On most areas of the body, the skin which is sloughed off is normally washed away at frequent intervals so that the slough-ing-off process is not noticeable. On the scalp, which is not normally washed as often as other parts of the body, the sloughed-off skin tends to accumulate. This skin together with the natural oils exuded by the scalp form a suitable environment for the growth of bacteria, and in fact certain bacteria are known to be associated with a dandruff condition.

The presence of bacteria in a dandruff condition suggests than an obvious cure is to treat the afflicted area with an agent which is capable of killing the bacteria. Heretofore, this obvious cure has not been successful although some oi the most powerful .bacteriostats have been used. Accordingly, it is believed that factors other than bacteriostatic activity are needed in order to provide an effective dandruff cure. Thus, sulfur is recognized as having a beneficial effect which is far greater than other materials which are tar more potent germicides. The particular properties of sulfur which render it helpful in combatting dandruff are not known.

It has become increasingly desirable to improve the bacteniostatic effect of detergent compositions. The term detergent is intended to denote soap and non-soap surface active agents. Many compounds are known that have germicidal or bacteriostatic properties against specific micro-organisms or groups thereof, but such property is generally destroyed or seriously impaired when the compound is incorporated into detergent compositions.

The retention of germicidal properties by a compound after inclusion in a detergent composition is only one of the necessary or desirable properties the compound must have to be considered as a desirable additive to the detergent composition designed for application to the human body. It is extremely important that the compound exhibit substantivity, i.e., the property of remaining on the skin and retaining germicidal activity over a period of time after washing and rinsing of the skin.

Other properties that are not concerned with the germicidal properties directly are, however, important as far as commercial use of the detergent composition by the general public is concerned. These include the following properties of a detergent bar, powder, liquid, etc. after inclusion of the specific compound:

(1) Initial whiteness (2) Color stability under sunlight exposure (3) Color stability under aging (4) Absence of discoloration by copper in stamping dies (5) Non-irritating to skin (6) No unpleasant odor Accordingly, it is an object of this invention to provide a shampoo composition including a material which is an effective anti-dandruff agent.

It is another object of this invention to provide a shampoo composition containing an active amount of l-hydroxy-Z-pyridinethione, salts :and esters thereof or related compounds.

It is ,a further object of this invention to provide a detergent composition which exhibits substantive germicidal properties and has a prolonged effect in maintaining skin germs and bacteria :at a reduced level.

It has been discovered that l-hydroXy-2-pyridinethione, salts and esters thereof, and related compounds have a totally unexpected effectiveness when used to treat the human scalp and other areas which are subject to dandruff condition. This anti-dandruff effect is all the more remarkable because it is not predictable on the basis of bacteriostatic activity. There are factors, unknown at present, which require that an effective anti-dandrufi? agent be more than simply an effective bacteriostat.

Clinical tests were performed which show the remarkable anti-dandrutf properties of the compositions of this invention. Four shampoo compositions were selected for the clinical tests. Two of the shampoo compositions contained 2.0% by weight, of the zinc salt of 1-hydroxy-2- pyridinethione. These two compositions embodied different detergent bases. The third shampoo composition is a control which has the same detergent base as one of the above two compositions. The fourth shampoo composition is a commercial paste shampoo containing a known bacteriostat (2,2-.thiobis (4,6-dichlorophenol)) and colloidal sulfur. The above four shampoo compositions are set forth in Table I below, with the shampoo compositions identified as #1, #2, #3 and #4, respectively.

TABLE I Shampoo compositions Code Letter #1 #3 Sulfated coconut fatty alcoholSodium salt Sodium stearate Sodium alkyl glyceryl ether sulfonate L Sodium acyl sarcosinate 2 Sodium sulfate Sodium chloride Trisodium phosphate Diethanolamide of coconut fatty acids Acetylated lanolin Phenyl mercuric acct e 3 Perfume 1-Hydroxy-2-pyridinethionc, no Water (Make up balance).

pH 2,2-thiobis(4,6-dichl0rophenol) Colloidal sulfur 1 Alkyl radicals derived from fatty alcohol, 25.3% from coconut and 3% from tallow.

2 Acyl radicals derived from coconut fatty acids. 3 3 5% solution in oleic acid in #1 and #2. 4 Maxlmum particle diameter10 microns.

The clinical test was conducted by first selecting 260 volunteers to shampoo their hair with their regular shampoo exactly one week before reporting to determine their initial dandruff grading. The grading was done by skilled graders who parted the hair over the complete scalp area sectionally to expose the entire scalp for visual examination. Grades from 10 to were assigned to each subject examined, according to the following scale:

10 Excellent, no scaling Good, slight scaling 2 Fair, some scaling 2 Moderate, moderate scaling 3 Poor, heavy scaling Very poor, heavy incrustations, erythema Only those receiving an initial grade of 6 or lower were retained for actual testing of the instant shampoo. They were given one of the four shampoos, told to shampoo at least twice a week for the first two weeks and to use no shampoo during the third week, after which they were graded. Then they were told to use their same designated shampoo at their pleasure for the fourth and fifth weeks and to use no shampoo during the sixth week, after which they were again graded for dandruff and also asked to rate their own dandruff condition on the trained graders scale. Neither the grader nor the subjects knew the identity of or distinction between the shampoos. The results of the tests by mean grades are summarized in Table II 2 Averaged scores rounded oft to one decimal place.

Careful analysis of this data shows accumulative change in average dandruff scores for each of the shampoos containing the zinc salt of 1-hydroxy-2-pyridinethione is significantly better than the other two shampoo compositions for both the 3-week and 6-week periods. Moreover, the subjects were able to observe the anti-dandruff effectiveness of the new shampoos relative to the control shampoos. It is thus clear that a detergent composition containing the zinc salt of 1-hydroxy-2-pyridinethione has a remarkable anti-dandruff efficacy which is not shown by the control which has the same detergent base. More importantly, shampoo composition #4 which contains a known baeteriostat has shown no improvement. Thus, the mere inclusion of a bacteriostat in a detergent composition does not assure that such composition will be effective in combatting dandruff. Certain other functions apparen ly m st be provid d o imp rt an i-dandruff propv respectively, contain 10 to 20 carbon atoms.

erties. These properties are inherent in the pyridinethione compositions of this invention.

The anti-dandruff shampoo compositions of this invention contain from about /4% to about 5% of the active material (1-hydroxy-2-pyridinethione compounds), preferably 1 /2% to 3%, in an aqueous detergent base. The compositions contain from about 5% to about 60% of a detergent. The detergent can be anionic, amphoteric, or cationic, although anionic organic detergent compounds are preferred, since they appear to provide the greatest anti-dandruff effectiveness when the shampoo compositions of this invention are used.

Anionic detergents include both the soap and non-soap detergents. Examples of suitable soaps are the sodium, potassium, ammonium and alkanolammonium salts of higher fatty acids c o e. Particularly useful are the sodium and potassium salts of the mixtures of fatty acids derived from coconut oil and tallow. Examples of anionic non-soap detergents are alkyl glyceryl ether sulfonates, alkyl sulfates, alkyl monoglyceride sulfates or sulfonates, alkyl polyethoxy ether sulfates, acyl sarcosinates, acyl esters of isethionates, acyl N-methyl taurides, alkyl benzene sulfanates, and alkyl phenol polyethoxy sulfonates. In these compounds the alkyl and acyl groups, They are used in the form of water-soluble salts, the sodium, potassium, ammonium and alkanolammonium salts, for example. Specific examples are sodium lauryl sulfate, potassium N-methyl lauroyl tauride; and triethanolamine dodecyl benzene sulfonate.

Suitable examples of cationic detergents are dilauryldimethyl ammonium chloride, diisobutyl phenoxy ethoxy ethyl dimethylbenzyl ammonium chloride, cetyl trimethyl ammonium bromide, N-cetyl pyridinium bromide and benzethonium chloride, which are classed as quaternary ammonium salts.

Suitable examples of amphoteric detergents are alkyl beta-imino dipropionates, and alkyl beta-amino propionates, wherein the alkyl group contains 10 to 20 carbon atoms, and basic quaternary ammonium compounds derived from 2-alkyl-substituted imidazoline.

Shampoo formulations can, of course, contain any of the usual shampoo additives such as color, perfume, thickeners, solvents, opacifiers, suds builders, conditioning agents, preservatives, buffers, and anti-static agents.

In view of the fact that shampoo formulation needs a small particle size in a dispersed medium, it has been found desirable to take a wet filter cake of about 50% of the zinc salt of l-hydroxy-2-pyridinethione, add 2% of Darvan 1 (sodium polyalkyl aryl sulfonate) and 0.3% of CMC-70 (medium viscosity sodium carboxymethyl cellulose) and then grind it in a pebble mill for about fifteen hours. The Darvan adds a charge to the individual particles which prevents subsequent coalescing and the CMC slows the settling, or after settling, aids the quick redispersion of the solution by mere stirring.

It has been discovered that l-hydroxy-2-pyridinethione compounds when incorporated in detergent compositions retain their bacteriostatic properties and are skin substantive. The use of detergent compositions embodying l-hydroxy-2-pyridinethione compounds retard the growth of body germs and bacteria for much longer periods than the detergent bases.

The specific precedures used to test the properties hereinbefore enumerated are described here in some detail, as there are no established procedures yet widely adopted in the art. The particular pyridinethione compound was blended at various concentrations with detergents which are anionic, cationic, nonionic, amphoteric and mixtures thereof, specific compositions thereof being set forth in Table III. A

TABLE in Code Letter Percent Detergent Compositions Cashmere Bouquet Potassium Oleate Ultrawet K (Anionic) Aerosol OS (Anionic)- Aerosol AY (Anionic) Carboxymethyl cellulose- Tween 80 (nonionic) Brij 35 (nonionic) Pluronie F-68 (nonionic) Sterox AJ (nonionic) Paraffin Intracol 0A (Cationic) Antaron FC-34 (amphoteric) 40 Mixed phosphates 60 60 60 60 Key to Table III:

The first five soaps listed are well known proprietary soaps without germicidal agents composed of a mixture of alkali metal salts of fatty acids, the general composition of Lux and Ivory being as follows:

Potassium oleate is a liquid soap formed from 11 parts H 0, 1 part KOH, 4 parts glycerin and 4 parts red oil (oleic acid).

Ultrawet K is a sodium salt of sulfonated Cm petroleum hydrocarbons.

Aerosol OS is a sodium alkyl naphthalene sulfonate. Aerosol AY" is diarnyl sodium sulfosuccinate. Tween 80 is a polyoxyethylene sorbitan monooleate. Brij 35 is a polyoxyethylene lauryl ether.

Pluronic F-68 is a condensate of ethylene oxide with a hydrocarbon base formed by condensing propylene oxide with propylene glycol.

Sterox AJ is a polyoxyethylene ether.

Intracol 0A is a long chain fatty acid amide containing several amine groups.

Antaron FC-34 is a complex fatty amide compound.

Bacteriostatic activity per so was tested by taking plugs of the blended solid compositions (liquid compositions were placed in peni-cups) and placing them on separate nutrient agar plates inoculated with Bacillus subtilis (found in soil and decomposing organic material), Staphylococcus aureus (found on the human skin) and Salmonella typhosa (cause of typhoid fever). These three bacteria are conventionally used in in vitro testing for activity and substantivity. The plates were incubated for 24 hours at about 37 C. and then the diameter of the zone of no bacterial growth around each plug was measured in millimeters (diameter of plug or peni-cup excluded) and recorded.

Substantivity was measured by soaking untanned calfskin buttons in an 8% aqueous solution of the test soap, then repeatedly rinsing the buttons in distilled water, and subsequently placing the buttons on nutrient agar plates inoculated with the same bacteria as noted above. Thereafter, the procedure is the same as following for bacterioitatic activity per se. The results are reported in Table TABLE IV Bacteriostatic activity and substantivity Inhib. Zone-Diameter (mm.)

Per-

Additive cent Soap Soap Plug Calfskin SAT A None (ControL.

TABLE IVCntinued 4 4 100 111585 00 4 m T 1 m m k 11 05 5 590 77 0 964 0 43 t 0 w 1 m 1 1 5 31A I O-B 0729 7 o m s mmrn n mm m mm m mmwm m n 1 111 am1t1 r11 1 bum 2t m e 222066 4212 624 0 404 00 65540 00 8606 50 19 49.210176121068566444 38 6 Z r 1 640t 6 1 76 0 6 8 140 7 U7 4 21 5 356699 1106254 59 6 b D A 2lsaw2 wmzwmnwmmwww2l%3m2 1%233%2w. mmmmllm%3%32m%2%%22222222222222% 21 2 .1 1 a 1 0 n 622040500105 00 8 428002200316428246 7420056526443008326095 462641 6 p a "w GHIJKLMBBCOOODEFGGGGHIJKLMBOCGGGGcHIJKLMnccoocooococcocoocoooccoo0 00 C 7 77 777 7 7 5 0 1111111 Qll LQOW 11111110 1L0 0 1111111111 IIQQQQQQQQQQQQQQQLLLLL LL L M0 P m m n u u Tm. n. n i n 1 r e .1 9 n 1n d d .1 .HO n .n m n gse .nb m 6 0 V. 0 m V. "e m m1 m V P 1 p M ma .1 iia l 1 YD u .5 m H n g t t m u nmn w u 1 m mw n C n .a a m mama w miwwm m n A w zlsem l bbaldmdo t 1 t y 1 1 i 1 y y y y y y P rrrrr u r u urrr rr m 222222 0 0 0 22222 22 2 9nd d d. a: a es at fi hts I: 111111 1 11111 11 1 u 0 N 2 0 n 9 draining for seconds. Thereafter, the left hand was uncovered, the right hand was covered with a neoprene activity and substantivity. Samples number 33 and 5 hand Applied Microglove, and the washing procedure repeated using unmedi cated, i.e., control soap. Thus the left hand serves as an unmedicated soap-washed control for the test soap-washed were further tested in a modification of the split-use washing test described by Quinn et al biology 2, 2024 (1954). In the modified test, first the right hand.

ed and the left hand covered The hands of each subject were washed three times each Then both hands were soaped day and bacterial counts made on the wash water used for 20 seconds by briskly rubbing the moistened medicated test bar with a small amount of wash water held in the cupped hands, the lather being worked up as far as the in the second washing on the third and fifth days of the test. The control or unmedicated soap is used for the washings at which bacterial counts are made so that none wrist for seconds, followed by rinsing the hands for of the test compound is present in the wash water to 20 seconds while immersed in the Wash water and then 75 influence the results. Aliquots of the wash water in which 9 each hand is washed were added to nutrient agar pour plates within one minute after completion of washing. The plates were incubated for 48 hours at 37 C., the bacterial colonies counted and the results calculated for the entire wash water. The results are summarized in 10 weeks, a very severe test, while the C (Ivory) soaps were tested after the normal two weeks aging at 125 F. as described for Table VI. Bacteriostatic activity and substantivity were then determined by the same methods described and reported in Table IV. Table VII shows 5 Table V. the post-aging results of these tests.

TABLE V Split-use hand washing test Three Day Results Five Day Results No. Subject Bacteria Count Bacteria Count (Millions) Percent (Millions) Percent Decrease Decrease On Right On Right Left Right Left Right V 2. 75 0. 48 82. 5 2. 12 0. 186 91. 2 W 2. 0. 84 61. 8 2. 15 0. 88. 4 X 2. 11 0. 47 77. 7 3. 33 0. 17 94. 9 Y 2. 94 1.93 34. 4 4. 32 0. 37 91. 4 Z 3.86 0.423 89.0

1 See Table IV.

From the results reported in Table V, it will be noted that the bacteriostatic activity and substantivity of the pyridinethione compounds can be demonstrated in an actual hand washing technique. Various other desirable properties of the same soap-pyridinethione compound mixtures of Table IV are reported in Table VI.

The initial whiteness is reported both after mixing of the pyr-idinethione compounds with the soap and after the soap bar had been formed in the conventional brass die.

The sunlight color stability was tested by breaking a soap bar in two and exposing one portion in an east window for two weeks, rotating it one-quarter turn daily.

The heat aging color stability was tested by placing a sample bar in a closed glass jar within an oven at 125 F. for two weeks which is presumed to be approximately equivalent to one year shelf storage.

The tests reported in Table VI are of the same numbered samples of Table IV but all the samples of Table IV were not tested here.

TAB-LE VI Color changes due to aging TABLE VII Bacteriostatic activity and sn'bstantivity after heat aging 1 See Table IV. R TrGrowth touching button in one place.

No. Initial Blend Initial Bar Heat Aged Sunlight Aged 1. White. White Slightly oil-white. Slightly oil-white. 2 dn do rlo D0, 15 Off-white- Off-white Brown Brown. 16. White White. Off-White- Cream.

' Off-white Light brown Light brown.

White. White White. dn rlo D Blue-black sheen on .do- D0.

surface only. Blue-black Butt Bufi.

sheen on surface only. 2

1 See Table IV.

2 This slight surface sheen, caused evidently by contact with the brass bar-forming die, was removed before the oven and sunlight aging tests.

It will be noted that samples 29 and 33 (zinc salt of 1-hydroxy-2-pyridinethione) gave excellent results in the color tests and, in fact, slightly better than the control bars containing no bacter-iostatic agent. Samples 48 and 50 (2,2'-dithiopyridine-1,l-dioxide) were also fairly good except for the surface sheen on the initial bar, a feature which might be overcome by changing the bar-forming conditions or dies.

The soaps showing the more desirable results in the color tests were subjected to bacteriostatic and substantivity tests after heat aging in an attempt to determine the extent of loss of bacteriostatic effect, if any, during heat aging. The B (LUX) soaps were aged for six After the aging tests, these samples retained their bacteriostatic activity and substantivity.

Detergent compositions N, O, P and Q were dry granular formulations of heavy-duty laundry type to which were added for separate test 1% by weight of zinc, sodium, disulfide and cetyl ammonium derivatives of the 1-hydroxy-2-pyridinethione. It was found that fabrics washed with these formulations had drastic reductions in bacteria count relative to fabrics washed in the same formulation without the active agent and further that this reduction was partly maintained after rinsing. Fabrics laundered in this manner would be particularly useful for wear or use that contacts the skin, or where large numbers of bacteria are encountered such as hospital and diaper laundries.

No skin irritation has been noted with any of the pyridinethione compounds tested.

The pyridinethione compounds do not impart odors to a detergent composition. This is a property highly desirable to both the manufacturer and the user of the detergent.

Not only do the pyridinethione compounds have exelement germicidal and substantive properites, which are maintained after prolonged aging, but these compounds also give excellent results in the various color tests which are so important in offering soap to the consumer market. As will be noted, many of the compounds stay white through the heat aging and sunlight aging tests and the others have only slight discoloration.

The specific examples reported in the tables have included 0.07 to by weight of the pyridinethione compounds in the detergent composition (based on solids) in order that specific comparisons could be made with the various compounds and also with various controls and prior art compounds. However, it will be obvious that a wider range of pyridinethione compounds can be used and we have found from 0.01 to to be generally a satisfactory range although this should not be a limiting feature of our invention.

It is obvious from these results that the l-hydroxy-Z- pyridinethione and its derivatives have properties which indicate their use as an ingredient of a germicidal or medicinal soap or detergent.

This invention is concerned with l-hydroxy-2-pyridinethi-one (and derivatives) which has the following structural formula in tautomeric form, the sulfur being attached to No. 2 position of the pyridine ring:

2-rnercaptopyridine l-oxide The salts and esters disclosed herein represent substitution of the corresponding cation for the hydrogen of one of the tautomeric forms. Depending, of course, on the valence of the cation involved, there may be more than one of the 1-hydroxy-2-pyridinethione rings in the com-pound. Although a number of compounds have been specifically disclose-d, it will be apparent to one skilled in the art that inorganic salts other than those tested are suitable. Further, other amine salts, quaternary arnmonium salts, and other esters are also suitable. The disulfide (2,2-dithiodipyridine-1,1-dioxide) represents the attachment of two 1-hydroxy-2-pyridinethione rings by the elimination of the two hydrogens from the sulfur atoms to give a sulfur-to-sulfur linkage. Other substituted or derived compounds of 1-hydroxy-2-pyridinethione which retain the bacteriostatic and substantive properties are considered to be within the scope of this invention.

The active pyridinethione compounds may be incorporated into liquid, bar or powder detergent compositions as desired to satisfy the particular product requirement. The detergent compositions herein are hydrophilic but the composition as a whole may include hydrophobic components, e.g., paraffin. Detergent compositions may, of course, include conventional additives such as perfume, color, emollients, binders, inert fillers, etc.

What is claimed is:

1. A method for combatting dandruff comprising the step of applying to the hair and scalp of humans a detergent composition comprising an amount of zinc pyridinethione sufficient to provide effective anti-dandruff control.

2. A method for combatting dandruff comprising the step of applying to the hair and scalp of humans a detergent composition comprising an amount of cadmium pyridinethione sufficient to provide effective antidandruff control.

3. A method for combatting dandruff comprising the step of applying to the hair and scalp of humans a detergent composition comprising an amount of tin pyridinethione sufficient to provide effective anti-dandruff control.

4. A method for combatting dandruff comprising the step of applying to the hair and scalp of humans a detergent composition comprising an amount of zirconium pyridinethione sufficient to provide effective anti-dandruff control.

5. A method for combatting dandruff comprising the step of treating the hair and scalp with a composition comprising an anionic detergent base and an amount of zinc pyridinethione sufficient to provide effective antidandruff control.

6. A method for combatting dandruff comprising the step of treating the hair and scalp with a composition comprising an anionic detergent base and an amount of cadmium pyridinethione sufficient to provide effective anti-dandruff control.

7. A method for combatting dandruff comprising the step of treating the hair and scalp with a composition comprising an anionic detergent base and an amount of tin pyridinethione sufficient to provide effective antidandruff control.

8. A method for combatting dandruff comprising the step of treating the hair and scalp with a composition comprising an anionic detergent base and an amount of zirconium pyridinethione sufficient to provide effective anti-dandruff control.

9. A method for combatting dandruff comprising the step of treating the hair and scalp with a shampoo composition comprising a detergent base and from about .25% to about 5% of zinc pyridinethione.

10. A method for combatting dandruff comprising the step of treating the hair and scalp with a shampoo composition comprising a detergent base and from about .25% to about 5% of cadmium pyridinethione.

11. A method for combatting dandruff comprising the step of treating the hair and scalp with a shampoo composition comprising a detergent base and from about .25 to about 5% of tin pyridinethione.

12. A method for combatting dandruff comprising the step of treating the hair and scalp with a shampoo composition comprising a detergent base and from about .25% to about 5% of zirconium pyridinethione.

References Cited by the Examiner UNITED STATES PATENTS 2,742,393 4/1956 Bernstein 260294.8 X 2,742,476 4/ 1956 Bernstein 260-2948 2,809,971 10/ 1957 Bernstein 260294.8 X 2,846,398 8/1958 Beaver et al. 252107 OTHER REFERENCES Elder et al.: Drug and Cosmetic Industry, vol. 77, No. 5, pp. 622-623, 714-717, 719 and 721 (November 1955).

Schimmel Briefs, No. 271, October 1957.

JULIAN S. LEVITT, Primary Examiner.

Claims (1)

1. A METHOD FOR CONBATING DANDRUFF COMPRISING THE STEP OF APPLYING TO THE HAIR AND SCALP OF HUMANS A DETERGENT COMPOSITION COMPRISING AN AMOUNT OF ZINC PYRIDINETHIONE SUFFICIENT TO PROVIDE EFFECTIVE ANTI-DANDRUFF CONTROL.
US44485865 1963-09-05 1965-04-01 Method of combatting dandruff with pyridinethiones metal salts detergent compositions Expired - Lifetime US3236733A (en)

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Cited By (239)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3281366A (en) * 1962-02-09 1966-10-25 Procter & Gamble Synergistic antibacterial compositions
US3489686A (en) * 1965-07-30 1970-01-13 Procter & Gamble Detergent compositions containing particle deposition enhancing agents
US3527864A (en) * 1966-11-18 1970-09-08 Procter & Gamble Compositions for topical application to animal tissue and method of enhancing penetration thereof
US3671634A (en) * 1970-02-16 1972-06-20 Vanderbilt Co R T Stable aqueous anti-dandruff shampoo containing captan
US3890434A (en) * 1971-10-18 1975-06-17 Olin Corp Hair and antiseptic formulations containing adducts of bis-(2-pyridyl-1-oxide) disulfide
US3928605A (en) * 1972-09-29 1975-12-23 Procter & Gamble Phenylantimony bis(2-pyridinethiol-1-oxide in antibacterial and antifungal compositions
US3950532A (en) * 1971-05-14 1976-04-13 L'oreal Topical application of cis of trans 3,4-thiolanediol to reduce the greasy appearance of hair and skin
US3961054A (en) * 1973-01-22 1976-06-01 Ciba-Geigy Corporation Combatting dandruff with mercapto quinoline N-oxides
US4033895A (en) * 1975-12-24 1977-07-05 Revlon, Inc. Non-irritating shampoo compositions containing stearyl amine oxide
US4080465A (en) * 1971-05-14 1978-03-21 Societe Anonyme Dite: L'oreal Topical application of cis or trans 3,4-thiolannediol to reduce or substantially eliminate the greasy appearance of the skin
US4089945A (en) * 1975-06-30 1978-05-16 The Procter & Gamble Company Antidandruff shampoos containing metallic cation complex to reduce in-use sulfide odor
FR2385390A1 (en) * 1977-04-01 1978-10-27 Marechal Raymond Topical compsn. for treatment of seborrhoeic alopecia, dandruff, etc. - contains an aromatic cpd. having phenolic or quinone groups and/or a mercury cpd. which inhibits enzyme mercapto groups
US4161526A (en) * 1978-07-20 1979-07-17 Sterling Drug Inc. Zinc salt prevention or removal of discoloration in pyrithione, pyrithione salt and dipyrithione compositions
US4185106A (en) * 1972-07-11 1980-01-22 Hoechst Aktiengesellschaft Pyridones as antidandruff agents
EP0023676A1 (en) * 1979-08-02 1981-02-11 REWO Chemische Werke GmbH Combination of active ingredients for cosmetics
JPS6023309A (en) * 1983-07-15 1985-02-05 Lion Corp Deodorant composition
EP0158481A2 (en) * 1984-03-28 1985-10-16 THE PROCTER & GAMBLE COMPANY Hair care compositions
US4552754A (en) * 1982-04-15 1985-11-12 Lion Corporation Hair cosmetic composition
US4557928A (en) * 1982-07-06 1985-12-10 Amway Corporation Anti-dandruff cream rinse conditioner
US4665064A (en) * 1983-10-31 1987-05-12 National Research Development Corporation Pharmaceutical compositions and methods for increasing zinc levels
US4711775A (en) * 1972-07-11 1987-12-08 Hoechst Aktiengesellschaft Cosmetic compositions
US4745071A (en) * 1985-09-05 1988-05-17 Sequoia-Turner Corporation Method for the volumetric differentiation of blood cells types
US4832950A (en) * 1984-08-29 1989-05-23 Kao Corporation Antimicrobial suspensions and antimicrobial hair treatment compositions
US5008202A (en) * 1988-11-29 1991-04-16 Sequoia Turner Corporation Blood diluent for red blood cell analysis
US5104865A (en) * 1983-09-23 1992-04-14 National Research Development Corporation Iron complexes of hydroxypyridones useful for treating iron overload
US5104645A (en) * 1990-02-02 1992-04-14 The Proctor & Gamble Company Antidandruff shampoo compositions
US5155119A (en) * 1992-03-05 1992-10-13 The Dow Chemical Company 3-(2-pyridinylthio)-N-oxide, 2-halo-2-propenenitrile compounds useful as antimicrobials
US5227156A (en) * 1992-04-14 1993-07-13 Amway Corporation Use of zinc compounds to stabilize a thiazolinone preservative in an anti-dandruff shampoo
US5776960A (en) * 1996-10-16 1998-07-07 Buckman Laboratories International, Inc. Synergistic antimicrobial compositions containing an ionene polymer and a pyrithione salt and methods of using the same
US5854266A (en) * 1994-12-05 1998-12-29 Olin Corporation Synergistic antimicrobial composition pyrithione and alcohol
US6054450A (en) * 1997-01-27 2000-04-25 Pacific Corporation Hair-care cosmetic compositions having dandruff formation-suppressing effect
WO2001000021A1 (en) * 1999-06-25 2001-01-04 Arch Chemicals, Inc. Pyrithione biocides enhanced by silver, copper, or zinc ions
US20030134759A1 (en) * 2001-11-02 2003-07-17 The Procter & Gamble Co. Composition containing a cationic polymer and water insoluble solid material
WO2003088965A1 (en) * 2002-04-22 2003-10-30 The Procter & Gamble Company Use of materials having zinc ionophoric behavior
US6645476B1 (en) 1999-07-15 2003-11-11 Clariant Gmbh Water-soluble polymers and their use in cosmetic and pharmaceutical compositions
US20030215522A1 (en) * 2002-04-22 2003-11-20 The Procter & Gamble Company Personal care compositions comprising a zinc containing material in an aqueous surfactant composition
US20040018165A1 (en) * 2002-07-23 2004-01-29 The Procter & Gamble Company Hair care compositions
US20040186030A1 (en) * 2003-01-27 2004-09-23 The Procter & Gamble Company Personal cleansing composition containing irregularly shaped particles and spherical particles
WO2004082648A1 (en) 2003-03-18 2004-09-30 The Procter & Gamble Company Composition comprising particulate zinc materials having a defined crystallite size
US20040213751A1 (en) * 2003-03-18 2004-10-28 Schwartz James Robert Augmentation of pyrithione activity or a polyvalent metal salt of pyrithione activity by zinc-containing layered material
US20040223941A1 (en) * 2003-03-18 2004-11-11 Schwartz James Robert Composition comprising zinc-containing layered material with a high relative zinc lability
US20050202984A1 (en) * 2003-03-18 2005-09-15 Schwartz James R. Composition comprising zinc-containing layered material with a high relative zinc lability
US7026308B1 (en) 1999-06-25 2006-04-11 The Procter & Gamble Company Topical anti-microbial compositions
US20060079422A1 (en) * 2004-10-08 2006-04-13 Sanjeev Midha Personal care composition containing a cleansing phase and a benefit phase
US20060089342A1 (en) * 2000-06-22 2006-04-27 Gavin David F Topical anti-microbial compositions
US20060269501A1 (en) * 2002-06-04 2006-11-30 Johnson Eric S Shampoo containing a gel network
US20060269502A1 (en) * 2002-06-04 2006-11-30 Johnson Eric S Shampoo containing a gel network and a non-guar galactomannan polymer derivative
US20070020220A1 (en) * 2005-04-27 2007-01-25 Procter & Gamble Personal care compositions
US20070110700A1 (en) * 2002-06-04 2007-05-17 Wells Robert L Shampoo containing a gel network
US20070128147A1 (en) * 2002-06-04 2007-06-07 The Procter & Gamble Company Composition comprising a particulate zinc material, a pyrithione or a polyvalent metal salt of a pyrithione and a gel network
US20070160555A1 (en) * 2006-01-09 2007-07-12 Staudigel James A Personal care compositions containing cationically modified starch and an anionic surfactant system
US20070207109A1 (en) * 2006-01-09 2007-09-06 Peffly Marjorie M Personal care compositions containing cationic synthetic copolymer and a detersive surfactant
US20070219276A1 (en) * 2006-03-20 2007-09-20 Pharmacyclics, Inc Water-soluble zinc ionophores, zinc chelators, and/or zinc complexes and use for treating cancer
US20070289613A1 (en) * 2002-06-04 2007-12-20 Geary Nicholas W Conditioning shampoo compositions containing select cationic conditioning polymers
US20070292380A1 (en) * 2006-06-16 2007-12-20 James Anthony Staudigel Hair conditioning composition containing a non-guar galactomannan polymer derivative
AU2005200050B2 (en) * 1999-06-25 2008-04-03 Arch Chemicals, Inc. Pyrithione biocides enchanced by silver, copper, or zinc ions
US20080095732A1 (en) * 2005-04-27 2008-04-24 Rosemarie Osborne Personal care compositions
US20080145328A1 (en) * 2006-12-15 2008-06-19 The Procter & Gamble Company Composition comprising pyrithione or a polyvalent metal salt of a pyrithione and furametpyr
US7455851B1 (en) 1999-06-25 2008-11-25 Arch Chemicals, Inc. Pyrithione biocides enhanced by silver, copper, or zinc ions
US20090005281A1 (en) * 2007-03-26 2009-01-01 Hutton Iii Howard David Compositions Containing Amine Oxide Surfactants or Soil Penetration Agents
US20090017147A1 (en) * 2005-01-14 2009-01-15 Sederma Cosmetic or Dermopharmaceutical Composition Comprising an Euglena Extract
US20090053165A1 (en) * 2007-08-20 2009-02-26 Mark Anthony Brown Method for Treating Damaged Hair
US20090087398A1 (en) * 2007-08-20 2009-04-02 Mark Anthony Brown Method for Treating Damaged Hair
KR100897727B1 (en) 1999-06-25 2009-05-18 아치 캐미컬스, 인크. Pyrithione biocides enhanced by silver, copper, or zinc ions
US20090176674A1 (en) * 2006-01-09 2009-07-09 The Procter & Gamble Company Personal care compositions containing cationic synthetic copolymer and a detersive surfactant
US20090176675A1 (en) * 2006-01-09 2009-07-09 Marjorie Mossman Peffly Personal Care Compositions Containing Cationically Modified Starch and an Anionic Surfactant System
EP2082723A1 (en) 1999-06-25 2009-07-29 The Procter and Gamble Company Topical anti-microbial compositions
US20090214607A1 (en) * 2005-05-13 2009-08-27 Sederma Topical use of teprenone
US20090232873A1 (en) * 2008-01-30 2009-09-17 The Procter & Gamble Company Personal Care Composition in the Form of an Article
US20090253666A1 (en) * 2006-08-03 2009-10-08 Sederma Composition comprising sarsasapogenin
US20090263342A1 (en) * 2008-04-16 2009-10-22 Glenn Jr Robert Wayne Non-Lathering Personal Care Composition in the Form of an Article
US20090269395A1 (en) * 2005-09-06 2009-10-29 Sederma Use of protoberberines as an active substance regulating the pilosebaceous unit
US20090274642A1 (en) * 2008-04-30 2009-11-05 Dawson Jr Thomas Larry Hair Care Compositions for Preventing Oxidative Damage to Hair, Methods of Use, and Methods of Marketing Such Compositions
US20090283106A1 (en) * 2008-05-15 2009-11-19 Wyeth Method of delivering a hair care benefit
AU2007203439B2 (en) * 2002-04-22 2010-02-18 Arch Chemical Use of materials having zinc ionophoric behavior
WO2010067327A1 (en) 2008-12-11 2010-06-17 Sederma Cosmetic composition containing acetylated oligoglucuronans
US20100167971A1 (en) * 2008-12-08 2010-07-01 Glenn Jr Robert Wayne Porous, dissolvable solid substrate and surface resident inorganic particulate perfume complexes
WO2010077653A2 (en) 2008-12-08 2010-07-08 The Procter & Gamble Company Personal care composition in the form of an article having a hydrophobic surface-resident coating
US20100179083A1 (en) * 2008-12-08 2010-07-15 Glenn Jr Robert Wayne Personal care composition in the form of an article having a porous, dissolvable solid structure
WO2010082176A2 (en) 2009-01-16 2010-07-22 Sederma Cosmetic composition containing kxk type peptides and uses
WO2010082177A2 (en) 2009-01-16 2010-07-22 Sederma New compounds, in particular peptides, compositions comprising them and cosmetic and dermopharmaceutical uses
WO2010082175A2 (en) 2009-01-16 2010-07-22 Sederma New compounds, in particular peptides, compositions comprising them and cosmetic and dermopharmaceutical uses
US20100298188A1 (en) * 2008-12-08 2010-11-25 Glenn Jr Robert Wayne Process of making an article for dissolution upon use to deliver surfactants
WO2010136965A2 (en) 2009-05-26 2010-12-02 Sederma Cosmetic use of tyr-arg dipeptide to combat cutaneous sa
WO2010141683A2 (en) 2009-06-04 2010-12-09 The Procter & Gamble Company Multiple product system for hair
US20110033507A1 (en) * 2006-02-16 2011-02-10 Sederma Polypeptides KXK and Their Use
US20110045036A1 (en) * 2006-05-05 2011-02-24 Sederma Cosmetic Compositions Comprising at Least One Peptide with at Least One Immobilized Aromatic Cycle
US20110166370A1 (en) * 2010-01-12 2011-07-07 Charles Winston Saunders Scattered Branched-Chain Fatty Acids And Biological Production Thereof
AU2008202828B2 (en) * 1999-06-25 2011-07-28 Arch Chemicals, Inc. Pyrithione biocides enhanced by silver, copper, or zinc ions
US20110182956A1 (en) * 2009-12-08 2011-07-28 Glenn Jr Robert Wayne Porous, Dissolvable Solid Substrate and Surface Resident Coating Comprising Matrix Microspheres
US20110189246A1 (en) * 2009-12-08 2011-08-04 Glenn Jr Robert Wayne Porous, Dissolvable Solid Substrate and a Cationic Surfactant Conditioner Material
WO2011103173A2 (en) 2010-02-17 2011-08-25 The Procter & Gamble Company Non-aerosol personal care compositions comprising an anti-irritation agent
WO2011103146A2 (en) 2010-02-16 2011-08-25 The Procter & Gamble Company A post foaming gel composition comprising an anti-irritation agent
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WO2011156584A1 (en) 2010-06-09 2011-12-15 The Procter & Gamble Company Methods of preparing personal care compositions
WO2011156551A1 (en) 2010-06-09 2011-12-15 The Procter & Gamble Company Method for preparing a non-ionic surfactant stable personal care dispersion
WO2011156558A1 (en) 2010-06-09 2011-12-15 The Procter & Gamble Company Cocoamide monoethanolamine (cmea) composition
WO2011156566A2 (en) 2010-06-09 2011-12-15 The Procter & Gamble Company Chemically stabilized anti-dandruff compositions for use in personal care compositions
WO2012009525A2 (en) 2010-07-15 2012-01-19 The Procter & Gamble Company Compositions comprising a near terminal-branched compound and methods of making the same
WO2012009660A2 (en) 2010-07-15 2012-01-19 The Procter & Gamble Company Detergent compositions comprising microbially produced fatty alcohols and derivatives thereof
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WO2012058216A2 (en) 2010-10-27 2012-05-03 The Gillette Company Composition dispensing device comprising a non-foaming hydrating composition
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WO2012058557A2 (en) 2010-10-28 2012-05-03 The Procter & Gamble Company Personal care compositions comprising a pyrithione and an iron chelator
WO2012118798A1 (en) 2011-02-28 2012-09-07 The Gillette Company Razor comprising a molded shaving aid composition comprising a pyrithione source
WO2012116466A1 (en) * 2011-02-28 2012-09-07 The Procter & Gamble Company Bar soap comprising pyrithione sources
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WO2012138696A2 (en) 2011-04-07 2012-10-11 The Procter & Gamble Company Shampoo compositions with increased deposition of polyacrylate microcapsules
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WO2013025893A1 (en) 2011-08-16 2013-02-21 The Gillette Company Personal care compositions comprising an anti-irritation agent
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WO2013092698A2 (en) 2011-12-22 2013-06-27 Akzo Nobel Chemicals International B.V. Bioactive compositions having hair anti aging activity
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WO2014165788A1 (en) 2013-04-05 2014-10-09 The Procter & Gamble Company Personal care composition comprising a pre-emulsified formulation
WO2014197427A2 (en) 2013-06-03 2014-12-11 R. J. Reynolds Tobacco Company Cosmetic compositions comprising tobacco seed-derived component
WO2014204662A1 (en) 2013-06-17 2014-12-24 The Gillette Company A glide member comprising low to no hygroscopic components for use with a razor
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WO2015035150A1 (en) 2013-09-05 2015-03-12 The Procter & Gamble Company Scalp care composition
US8980876B2 (en) 2010-10-28 2015-03-17 The Procter & Gamble Company Inhibition of microbial growth by aconitase inhibition
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US9050477B2 (en) 2009-04-17 2015-06-09 Sederma Cosmetic compositions comprising oridonin and new cosmetic uses
WO2015100122A1 (en) 2013-12-23 2015-07-02 Lubrizol Advanced Materials, Inc. Suspension and stability agent for antidandruff hair care compositions
WO2015148309A1 (en) 2014-03-26 2015-10-01 The Gillette Company Razor comprising a molded shaving aid composition comprising a thermally resilient sensate
US9162085B2 (en) 2011-04-07 2015-10-20 The Procter & Gamble Company Personal cleansing compositions with increased deposition of polyacrylate microcapsules
EP2937112A1 (en) 2014-04-25 2015-10-28 The Procter and Gamble Company Method of inhibiting copper deposition on hair
WO2015164680A1 (en) 2014-04-24 2015-10-29 The Procter & Gamble Company Scalp care composition
WO2015164137A1 (en) 2014-04-25 2015-10-29 The Procter & Gamble Company Method of inhibiting copper deposition on hair
WO2015164140A1 (en) 2014-04-25 2015-10-29 The Procter & Gamble Company Shampoo composition comprising gel matrix and histidine
WO2015164138A1 (en) 2014-04-25 2015-10-29 The Procter & Gamble Company Method of inhibiting copper deposition on hair
US9173826B2 (en) 2010-02-16 2015-11-03 The Procter & Gamble Company Porous, dissolvable solid substrate and surface resident coating comprising a zync pyrithione
US9186642B2 (en) 2010-04-28 2015-11-17 The Procter & Gamble Company Delivery particle
US9198847B2 (en) 2004-11-05 2015-12-01 The Procter & Gamble Company Personal care composition containing a non-guar galactomannan polymer derivative and an anionic surfactant system
WO2015195738A1 (en) 2014-06-20 2015-12-23 The Procter & Gamble Company Stability of zinc pyrithione dispersions
US9233055B2 (en) 2012-10-12 2016-01-12 The Procter & Gamble Company Personal care composition in the form of a dissolvable article
US9271912B2 (en) 2012-06-13 2016-03-01 The Procter & Gamble Company Personal care compositions comprising a pH tuneable gellant and methods of using
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WO2016054450A1 (en) 2014-10-03 2016-04-07 The Procter & Gamble Company Method of improved volume and combability using personal care composition comprising a pre-emulsified formulation
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WO2016090207A1 (en) 2014-12-05 2016-06-09 The Procter & Gamble Company Composition for hair frizz reduction
WO2016100466A1 (en) 2014-12-18 2016-06-23 Lubrizol Advanced Materials, Inc. Amphiphilic suspension and stability agent for antidandruff hair care compositions
US9381148B2 (en) 2003-03-18 2016-07-05 The Procter & Gamble Company Composition comprising particulate zinc material with a high relative zinc lability
US9434993B2 (en) 2011-02-22 2016-09-06 The Procter & Gamble Company Systems for identifying cosmetic agents for skin care compositions
WO2016172410A1 (en) 2015-04-23 2016-10-27 The Procter & Gamble Company A method of achieving targeted delivery of a scalp cleansing composition and a conditioning shampoo composition
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WO2017097817A1 (en) 2015-12-08 2017-06-15 Clariant International Ltd A shampoo composition comprising at least one oligoester ammonium salt
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2742476A (en) * 1953-10-26 1956-04-17 Olin Mathieson Derivatives of 2-mercaptopyridine 1-oxide
US2742393A (en) * 1953-05-19 1956-04-17 Olin Mathieson Derivatives of 2-mercaptopyridine-1-oxide
US2809971A (en) * 1955-11-22 1957-10-15 Olin Mathieson Heavy-metal derivatives of 1-hydroxy-2-pyridinethiones and method of preparing same
US2846398A (en) * 1955-12-27 1958-08-05 Monsanto Chemicals Antiseptic detergent composition

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2742393A (en) * 1953-05-19 1956-04-17 Olin Mathieson Derivatives of 2-mercaptopyridine-1-oxide
US2742476A (en) * 1953-10-26 1956-04-17 Olin Mathieson Derivatives of 2-mercaptopyridine 1-oxide
US2809971A (en) * 1955-11-22 1957-10-15 Olin Mathieson Heavy-metal derivatives of 1-hydroxy-2-pyridinethiones and method of preparing same
US2846398A (en) * 1955-12-27 1958-08-05 Monsanto Chemicals Antiseptic detergent composition

Cited By (330)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3281366A (en) * 1962-02-09 1966-10-25 Procter & Gamble Synergistic antibacterial compositions
US3489686A (en) * 1965-07-30 1970-01-13 Procter & Gamble Detergent compositions containing particle deposition enhancing agents
US3527864A (en) * 1966-11-18 1970-09-08 Procter & Gamble Compositions for topical application to animal tissue and method of enhancing penetration thereof
US3671634A (en) * 1970-02-16 1972-06-20 Vanderbilt Co R T Stable aqueous anti-dandruff shampoo containing captan
US3950532A (en) * 1971-05-14 1976-04-13 L'oreal Topical application of cis of trans 3,4-thiolanediol to reduce the greasy appearance of hair and skin
US4080465A (en) * 1971-05-14 1978-03-21 Societe Anonyme Dite: L'oreal Topical application of cis or trans 3,4-thiolannediol to reduce or substantially eliminate the greasy appearance of the skin
US3890434A (en) * 1971-10-18 1975-06-17 Olin Corp Hair and antiseptic formulations containing adducts of bis-(2-pyridyl-1-oxide) disulfide
US4711775A (en) * 1972-07-11 1987-12-08 Hoechst Aktiengesellschaft Cosmetic compositions
US4185106A (en) * 1972-07-11 1980-01-22 Hoechst Aktiengesellschaft Pyridones as antidandruff agents
US3928605A (en) * 1972-09-29 1975-12-23 Procter & Gamble Phenylantimony bis(2-pyridinethiol-1-oxide in antibacterial and antifungal compositions
US3961054A (en) * 1973-01-22 1976-06-01 Ciba-Geigy Corporation Combatting dandruff with mercapto quinoline N-oxides
US4089945A (en) * 1975-06-30 1978-05-16 The Procter & Gamble Company Antidandruff shampoos containing metallic cation complex to reduce in-use sulfide odor
US4033895A (en) * 1975-12-24 1977-07-05 Revlon, Inc. Non-irritating shampoo compositions containing stearyl amine oxide
FR2385390A1 (en) * 1977-04-01 1978-10-27 Marechal Raymond Topical compsn. for treatment of seborrhoeic alopecia, dandruff, etc. - contains an aromatic cpd. having phenolic or quinone groups and/or a mercury cpd. which inhibits enzyme mercapto groups
US4161526A (en) * 1978-07-20 1979-07-17 Sterling Drug Inc. Zinc salt prevention or removal of discoloration in pyrithione, pyrithione salt and dipyrithione compositions
US4307089A (en) * 1979-08-02 1981-12-22 Rewo Chemische Werke Gmbh Compositions of pyrithione metal salts and undecylenic acid alkylolamide derivatives
EP0023676A1 (en) * 1979-08-02 1981-02-11 REWO Chemische Werke GmbH Combination of active ingredients for cosmetics
US4552754A (en) * 1982-04-15 1985-11-12 Lion Corporation Hair cosmetic composition
US4557928A (en) * 1982-07-06 1985-12-10 Amway Corporation Anti-dandruff cream rinse conditioner
JPS6240328B2 (en) * 1983-07-15 1987-08-27 Lion Corp
JPS6023309A (en) * 1983-07-15 1985-02-05 Lion Corp Deodorant composition
US5104865A (en) * 1983-09-23 1992-04-14 National Research Development Corporation Iron complexes of hydroxypyridones useful for treating iron overload
US4894455A (en) * 1983-10-31 1990-01-16 National Research Development Corporation Pharmaceutically active zinc complexes
US4665064A (en) * 1983-10-31 1987-05-12 National Research Development Corporation Pharmaceutical compositions and methods for increasing zinc levels
EP0158481A2 (en) * 1984-03-28 1985-10-16 THE PROCTER & GAMBLE COMPANY Hair care compositions
EP0158481A3 (en) * 1984-03-28 1986-12-30 THE PROCTER & GAMBLE COMPANY Hair care compositions
US4832950A (en) * 1984-08-29 1989-05-23 Kao Corporation Antimicrobial suspensions and antimicrobial hair treatment compositions
US4745071A (en) * 1985-09-05 1988-05-17 Sequoia-Turner Corporation Method for the volumetric differentiation of blood cells types
US5008202A (en) * 1988-11-29 1991-04-16 Sequoia Turner Corporation Blood diluent for red blood cell analysis
US5104645A (en) * 1990-02-02 1992-04-14 The Proctor & Gamble Company Antidandruff shampoo compositions
US5155119A (en) * 1992-03-05 1992-10-13 The Dow Chemical Company 3-(2-pyridinylthio)-N-oxide, 2-halo-2-propenenitrile compounds useful as antimicrobials
US5227156A (en) * 1992-04-14 1993-07-13 Amway Corporation Use of zinc compounds to stabilize a thiazolinone preservative in an anti-dandruff shampoo
US5854266A (en) * 1994-12-05 1998-12-29 Olin Corporation Synergistic antimicrobial composition pyrithione and alcohol
US5776960A (en) * 1996-10-16 1998-07-07 Buckman Laboratories International, Inc. Synergistic antimicrobial compositions containing an ionene polymer and a pyrithione salt and methods of using the same
US6008236A (en) * 1996-10-16 1999-12-28 Buckman Laboratories International, Inc. Synergistic antimicrobial compositions containing an ionene polymer and a pyrithione salt and methods of using the same
US6054450A (en) * 1997-01-27 2000-04-25 Pacific Corporation Hair-care cosmetic compositions having dandruff formation-suppressing effect
AU2008202828A8 (en) * 1999-06-25 2011-08-11 Arch Chemicals, Inc. Pyrithione biocides enhanced by silver, copper, or zinc ions
WO2001000021A1 (en) * 1999-06-25 2001-01-04 Arch Chemicals, Inc. Pyrithione biocides enhanced by silver, copper, or zinc ions
AU2008202828B8 (en) * 1999-06-25 2011-08-11 Arch Chemicals, Inc. Pyrithione biocides enhanced by silver, copper, or zinc ions
US7455851B1 (en) 1999-06-25 2008-11-25 Arch Chemicals, Inc. Pyrithione biocides enhanced by silver, copper, or zinc ions
KR100897727B1 (en) 1999-06-25 2009-05-18 아치 캐미컬스, 인크. Pyrithione biocides enhanced by silver, copper, or zinc ions
AU2008202828B2 (en) * 1999-06-25 2011-07-28 Arch Chemicals, Inc. Pyrithione biocides enhanced by silver, copper, or zinc ions
US20050158263A1 (en) * 1999-06-25 2005-07-21 Arch Chemicals, Inc., A Corporation Of The State Of Virginia Pyrithione biocides enhanced by zinc metal ions and organic amines
US8796252B2 (en) 1999-06-25 2014-08-05 Arch Chemicals, Inc. Pyrithione biocides enhanced by zinc metal ions and organic amines
US7026308B1 (en) 1999-06-25 2006-04-11 The Procter & Gamble Company Topical anti-microbial compositions
AU2005200050B2 (en) * 1999-06-25 2008-04-03 Arch Chemicals, Inc. Pyrithione biocides enchanced by silver, copper, or zinc ions
US6908912B2 (en) 1999-06-25 2005-06-21 Arch Chemicals, Inc. Pyrithione biocides enhanced by zinc metal ions and organic amines
EP2082723A1 (en) 1999-06-25 2009-07-29 The Procter and Gamble Company Topical anti-microbial compositions
US8206732B2 (en) 1999-06-25 2012-06-26 Arch Chemicals, Inc. Pyrithione biocides enhanced by silver, copper, or zinc ions
US6645476B1 (en) 1999-07-15 2003-11-11 Clariant Gmbh Water-soluble polymers and their use in cosmetic and pharmaceutical compositions
US7674785B2 (en) 2000-06-22 2010-03-09 The Procter & Gamble Company Topical anti-microbial compositions
US20060089342A1 (en) * 2000-06-22 2006-04-27 Gavin David F Topical anti-microbial compositions
US6849584B2 (en) 2001-11-02 2005-02-01 The Procter & Gamble Company Composition containing a cationic polymer and water insoluble solid material
US20030134759A1 (en) * 2001-11-02 2003-07-17 The Procter & Gamble Co. Composition containing a cationic polymer and water insoluble solid material
AU2007203439B2 (en) * 2002-04-22 2010-02-18 Arch Chemical Use of materials having zinc ionophoric behavior
US20030215522A1 (en) * 2002-04-22 2003-11-20 The Procter & Gamble Company Personal care compositions comprising a zinc containing material in an aqueous surfactant composition
US20040058855A1 (en) * 2002-04-22 2004-03-25 Schwartz James R. Use of materials having zinc ionophoric behavior
WO2003088965A1 (en) * 2002-04-22 2003-10-30 The Procter & Gamble Company Use of materials having zinc ionophoric behavior
CN1646124B (en) 2002-04-22 2010-05-26 宝洁公司;阿尔什化学公司 Use of materials having zinc ionophoric behavior
US8119168B2 (en) 2002-04-22 2012-02-21 The Procter & Gamble Company Personal care compositions comprising a zinc containing material in an aqueous surfactant composition
JP2005526111A (en) * 2002-04-22 2005-09-02 アーチ・ケミカルズ・インコーポレイテッドArch Chemicals, Inc. Use of a substance having a zinc ionophore property
US20080138442A1 (en) * 2002-04-22 2008-06-12 Eric Scott Johnson Personal care compositions comprising a zinc containing material in an aqueous surfactant composition
US20060269501A1 (en) * 2002-06-04 2006-11-30 Johnson Eric S Shampoo containing a gel network
US20070289613A1 (en) * 2002-06-04 2007-12-20 Geary Nicholas W Conditioning shampoo compositions containing select cationic conditioning polymers
US8349301B2 (en) 2002-06-04 2013-01-08 The Procter & Gamble Company Shampoo containing a gel network
US20080057016A1 (en) * 2002-06-04 2008-03-06 Geary Nicholas W Conditioning shampoo compositions containing select cationic conditioning polymers
US8361450B2 (en) 2002-06-04 2013-01-29 The Procter & Gamble Company Shampoo containing a gel network and a non-guar galactomannan polymer derivative
US20070128147A1 (en) * 2002-06-04 2007-06-07 The Procter & Gamble Company Composition comprising a particulate zinc material, a pyrithione or a polyvalent metal salt of a pyrithione and a gel network
US7598213B2 (en) 2002-06-04 2009-10-06 The Procter & Gamble Company Conditioning shampoo compositions containing select cationic conditioning polymers
US7585827B2 (en) 2002-06-04 2009-09-08 The Procter & Gamble Company Conditioning shampoo compositions containing a mixture of select cationic conditioning polymers
US8349302B2 (en) 2002-06-04 2013-01-08 The Procter & Gamble Company Shampoo containing a gel network and a non-guar galactomannan polymer derivative
US20070110700A1 (en) * 2002-06-04 2007-05-17 Wells Robert L Shampoo containing a gel network
US8470305B2 (en) 2002-06-04 2013-06-25 The Procter & Gamble Company Shampoo containing a gel network
US8361448B2 (en) 2002-06-04 2013-01-29 The Procter & Gamble Company Shampoo containing a gel network
US9381382B2 (en) 2002-06-04 2016-07-05 The Procter & Gamble Company Composition comprising a particulate zinc material, a pyrithione or a polyvalent metal salt of a pyrithione and a gel network
US8361449B2 (en) 2002-06-04 2013-01-29 The Procter & Gamble Company Shampoo containing a gel network
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US20060269502A1 (en) * 2002-06-04 2006-11-30 Johnson Eric S Shampoo containing a gel network and a non-guar galactomannan polymer derivative
US20040018165A1 (en) * 2002-07-23 2004-01-29 The Procter & Gamble Company Hair care compositions
US20040186030A1 (en) * 2003-01-27 2004-09-23 The Procter & Gamble Company Personal cleansing composition containing irregularly shaped particles and spherical particles
US20080138441A1 (en) * 2003-03-18 2008-06-12 James Robert Schwartz Composition comprising zinc-containing layered material with a high relative zinc lability
US20040223941A1 (en) * 2003-03-18 2004-11-11 Schwartz James Robert Composition comprising zinc-containing layered material with a high relative zinc lability
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US20050202984A1 (en) * 2003-03-18 2005-09-15 Schwartz James R. Composition comprising zinc-containing layered material with a high relative zinc lability
US20040213751A1 (en) * 2003-03-18 2004-10-28 Schwartz James Robert Augmentation of pyrithione activity or a polyvalent metal salt of pyrithione activity by zinc-containing layered material
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US20060079422A1 (en) * 2004-10-08 2006-04-13 Sanjeev Midha Personal care composition containing a cleansing phase and a benefit phase
US7531497B2 (en) 2004-10-08 2009-05-12 The Procter & Gamble Company Personal care composition containing a cleansing phase and a benefit phase
US9198847B2 (en) 2004-11-05 2015-12-01 The Procter & Gamble Company Personal care composition containing a non-guar galactomannan polymer derivative and an anionic surfactant system
US8741357B2 (en) 2005-01-14 2014-06-03 Sederma Sas Cosmetic or dermopharmaceutical composition comprising an euglena extract
US20090017147A1 (en) * 2005-01-14 2009-01-15 Sederma Cosmetic or Dermopharmaceutical Composition Comprising an Euglena Extract
US20080095732A1 (en) * 2005-04-27 2008-04-24 Rosemarie Osborne Personal care compositions
US8871717B2 (en) 2005-04-27 2014-10-28 The Procter & Gamble Company Personal care compositions
US20070020220A1 (en) * 2005-04-27 2007-01-25 Procter & Gamble Personal care compositions
US9616011B2 (en) 2005-04-27 2017-04-11 The Procter & Gamble Company Personal care compositions
US10130577B2 (en) 2005-04-27 2018-11-20 The Procter & Gamble Company Personal care compositions
US20090214607A1 (en) * 2005-05-13 2009-08-27 Sederma Topical use of teprenone
US20090269395A1 (en) * 2005-09-06 2009-10-29 Sederma Use of protoberberines as an active substance regulating the pilosebaceous unit
US8846019B2 (en) 2005-09-06 2014-09-30 Sederma Use of protoberberines as an active substance regulating the pilosebaceous unit
EP3281619A1 (en) 2005-09-16 2018-02-14 The Procter and Gamble Company Shampoo containing a gel network
US20070160555A1 (en) * 2006-01-09 2007-07-12 Staudigel James A Personal care compositions containing cationically modified starch and an anionic surfactant system
US20070207109A1 (en) * 2006-01-09 2007-09-06 Peffly Marjorie M Personal care compositions containing cationic synthetic copolymer and a detersive surfactant
US20090176674A1 (en) * 2006-01-09 2009-07-09 The Procter & Gamble Company Personal care compositions containing cationic synthetic copolymer and a detersive surfactant
US9427391B2 (en) 2006-01-09 2016-08-30 The Procter & Gamble Company Personal care compositions containing cationic synthetic copolymer and a detersive surfactant
US20090176675A1 (en) * 2006-01-09 2009-07-09 Marjorie Mossman Peffly Personal Care Compositions Containing Cationically Modified Starch and an Anionic Surfactant System
US8404648B2 (en) 2006-02-16 2013-03-26 Sederma Polypeptides KXK and their use
US20110033507A1 (en) * 2006-02-16 2011-02-10 Sederma Polypeptides KXK and Their Use
US20110034431A1 (en) * 2006-03-20 2011-02-10 Jonathan L. Sessler Water-soluble zinc ionophores, zinc chelators, and/or zinc complexes and use for treating cancer
US20070219276A1 (en) * 2006-03-20 2007-09-20 Pharmacyclics, Inc Water-soluble zinc ionophores, zinc chelators, and/or zinc complexes and use for treating cancer
US8507531B2 (en) 2006-03-20 2013-08-13 Jonathan L. Sessler Water-soluble zinc ionophores, zinc chelators, and/or zinc complexes and use for treating cancer
US7528125B2 (en) 2006-03-20 2009-05-05 Jonathan L. Sessler Water-soluble zinc ionophores, zinc chelators, and/or zinc complexes and use for treating cancer
US7838536B2 (en) 2006-03-20 2010-11-23 Jonathan L. Sessler Water-soluble zinc ionophores, zinc chelators, and/or zinc complexes and use for treating cancer
US20090209509A1 (en) * 2006-03-20 2009-08-20 Jonathan L. Sessler Water-soluble zinc ionophores, zinc chelators, and/or zinc complexes and use for treating cancer
US8507649B2 (en) 2006-05-05 2013-08-13 Sederma Cosmetic compositions comprising at least one peptide with at least one immobilized aromatic cycle
US20110045036A1 (en) * 2006-05-05 2011-02-24 Sederma Cosmetic Compositions Comprising at Least One Peptide with at Least One Immobilized Aromatic Cycle
EP2510982A1 (en) 2006-05-05 2012-10-17 Sederma Cosmetic compositions comprising at least one peptide with at least one immobilized aromatic cycle
US20070292380A1 (en) * 2006-06-16 2007-12-20 James Anthony Staudigel Hair conditioning composition containing a non-guar galactomannan polymer derivative
US8361516B2 (en) 2006-08-03 2013-01-29 Sederma Composition comprising sarsasapogenin
US20090253666A1 (en) * 2006-08-03 2009-10-08 Sederma Composition comprising sarsasapogenin
US8673274B2 (en) 2006-12-15 2014-03-18 The Procter & Gamble Company Composition comprising pyrithione or a polyvalent metal salt of a pyrithione and furametpyr
US20080145328A1 (en) * 2006-12-15 2008-06-19 The Procter & Gamble Company Composition comprising pyrithione or a polyvalent metal salt of a pyrithione and furametpyr
US20090005281A1 (en) * 2007-03-26 2009-01-01 Hutton Iii Howard David Compositions Containing Amine Oxide Surfactants or Soil Penetration Agents
US20090053165A1 (en) * 2007-08-20 2009-02-26 Mark Anthony Brown Method for Treating Damaged Hair
US20090087398A1 (en) * 2007-08-20 2009-04-02 Mark Anthony Brown Method for Treating Damaged Hair
US20090232873A1 (en) * 2008-01-30 2009-09-17 The Procter & Gamble Company Personal Care Composition in the Form of an Article
US8765170B2 (en) 2008-01-30 2014-07-01 The Procter & Gamble Company Personal care composition in the form of an article
US20090263342A1 (en) * 2008-04-16 2009-10-22 Glenn Jr Robert Wayne Non-Lathering Personal Care Composition in the Form of an Article
US8273333B2 (en) 2008-04-16 2012-09-25 The Procter & Gamble Company Non-lathering personal care composition in the form of an article
EP2666458A2 (en) 2008-04-16 2013-11-27 The Procter and Gamble Company Pre-mix for a non-lathering personal care article, the article having the form of a solid foam
EP2666457A2 (en) 2008-04-16 2013-11-27 The Procter and Gamble Company Process for forming a non-lathering personal care article in the form of a dissolvable solid foam
US8628706B2 (en) 2008-04-16 2014-01-14 The Procter & Gamble Company Non-lathering personal care composition in the form of an article
US20090274642A1 (en) * 2008-04-30 2009-11-05 Dawson Jr Thomas Larry Hair Care Compositions for Preventing Oxidative Damage to Hair, Methods of Use, and Methods of Marketing Such Compositions
US20090283106A1 (en) * 2008-05-15 2009-11-19 Wyeth Method of delivering a hair care benefit
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US8415287B2 (en) 2008-12-08 2013-04-09 The Procter & Gamble Company Porous, dissolvable solid substrate and surface resident inorganic particulate perfume complexes
US20100179083A1 (en) * 2008-12-08 2010-07-15 Glenn Jr Robert Wayne Personal care composition in the form of an article having a porous, dissolvable solid structure
US8461090B2 (en) 2008-12-08 2013-06-11 The Procter & Gamble Company Personal care composition in the form of an article having a porous, dissolvable solid structure
US20100173817A1 (en) * 2008-12-08 2010-07-08 Glenn Jr Robert Wayne Porous, dissolvable solid substrate and surface resident starch perfume complexes
US20100167971A1 (en) * 2008-12-08 2010-07-01 Glenn Jr Robert Wayne Porous, dissolvable solid substrate and surface resident inorganic particulate perfume complexes
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US20100279905A1 (en) * 2008-12-08 2010-11-04 Glenn Jr Robert Wayne Porous, dissolvable solid substrates and surface resident cyclodextrin perfume complexes
US20100291165A1 (en) * 2008-12-08 2010-11-18 Glenn Jr Robert Wayne Personal care composition in the form of an article having a hydrophobic surface-resident coating
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US20100298188A1 (en) * 2008-12-08 2010-11-25 Glenn Jr Robert Wayne Process of making an article for dissolution upon use to deliver surfactants
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WO2010082175A2 (en) 2009-01-16 2010-07-22 Sederma New compounds, in particular peptides, compositions comprising them and cosmetic and dermopharmaceutical uses
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US8697656B2 (en) 2009-01-16 2014-04-15 Sederma Compounds, in particular peptides, compositions comprising them and cosmetic and dermo-pharmaceutical uses
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US9050477B2 (en) 2009-04-17 2015-06-09 Sederma Cosmetic compositions comprising oridonin and new cosmetic uses
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US20110182956A1 (en) * 2009-12-08 2011-07-28 Glenn Jr Robert Wayne Porous, Dissolvable Solid Substrate and Surface Resident Coating Comprising Matrix Microspheres
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US20110189246A1 (en) * 2009-12-08 2011-08-04 Glenn Jr Robert Wayne Porous, Dissolvable Solid Substrate and a Cationic Surfactant Conditioner Material
US8933131B2 (en) 2010-01-12 2015-01-13 The Procter & Gamble Company Intermediates and surfactants useful in household cleaning and personal care compositions, and methods of making the same
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US20110166370A1 (en) * 2010-01-12 2011-07-07 Charles Winston Saunders Scattered Branched-Chain Fatty Acids And Biological Production Thereof
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US10143632B2 (en) 2011-04-07 2018-12-04 The Procter And Gamble Company Shampoo compositions with increased deposition of polyacrylate microcapsules
US9162085B2 (en) 2011-04-07 2015-10-20 The Procter & Gamble Company Personal cleansing compositions with increased deposition of polyacrylate microcapsules
WO2012138696A2 (en) 2011-04-07 2012-10-11 The Procter & Gamble Company Shampoo compositions with increased deposition of polyacrylate microcapsules
WO2012162331A2 (en) 2011-05-26 2012-11-29 The Procter & Gamble Company Compositions comprising an efficient perfume bloom
US8425622B2 (en) 2011-05-27 2013-04-23 The Procter & Gamble Company Soluble solid hair coloring article
US8439981B2 (en) 2011-05-27 2013-05-14 The Procter & Gamble Company Soluble solid hair coloring article
WO2012174096A2 (en) 2011-06-13 2012-12-20 The Procter & Gamble Company Personal care compositions comprising a di-amido gellant and methods of using
WO2012174091A2 (en) 2011-06-13 2012-12-20 The Procter & Gamble Company PERSONAL CARE COMPOSITIONS COMPRISING A pH TUNEABLE GELLANT AND METHODS OF USING
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US20130045263A1 (en) * 2011-08-15 2013-02-21 Edward Dewey Smith, III Personal Care Compositions Having Dried Zinc Pyrithione-Polymer Aggregates
WO2013025772A2 (en) 2011-08-16 2013-02-21 The Gillette Company Composition dispensing device comprising a moisturizing composition
WO2013025893A1 (en) 2011-08-16 2013-02-21 The Gillette Company Personal care compositions comprising an anti-irritation agent
WO2013025886A1 (en) 2011-08-16 2013-02-21 The Gillette Company Shave preparations comprising an anti-irritation agent
WO2013025891A1 (en) 2011-08-16 2013-02-21 The Gillette Company An aerosol shave composition comprising a hydrophobical agent forming at least one microdroplet and an anti-irritation agent
WO2013025857A1 (en) 2011-08-16 2013-02-21 The Gillette Company Skin engaging member comprising an anti-irritation agent
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US9272164B2 (en) 2011-10-07 2016-03-01 The Procter & Gamble Company Method of achieving improved hair feel
WO2013052771A2 (en) 2011-10-07 2013-04-11 The Procter & Gamble Company Personal care compositions and methods of making same
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US8980239B2 (en) 2011-10-07 2015-03-17 The Procter & Gamble Company Personal care compositions and methods of making same
US9913797B2 (en) 2011-12-22 2018-03-13 Isp Investments Llc Bioactive compositions having hair anti aging activity
WO2013092698A2 (en) 2011-12-22 2013-06-27 Akzo Nobel Chemicals International B.V. Bioactive compositions having hair anti aging activity
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WO2013106367A2 (en) 2012-01-09 2013-07-18 The Procter & Gamble Company Hair care compositions
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WO2014028569A1 (en) 2012-08-15 2014-02-20 The Procter & Gamble Company Systems, models and methods for identifying and evaluating skin-active agents effective for treating an array of skin disorders
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US9804152B1 (en) 2012-08-15 2017-10-31 The Procter & Gamble Company Human ex vivo skin model and its use in methods of identifying modulators of skin inflammation
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WO2014137770A1 (en) 2013-03-04 2014-09-12 The Gillette Company Article for carrying a glide member for use with a razor
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WO2014138141A1 (en) 2013-03-05 2014-09-12 The Procter & Gamble Company Mixed sugar compositions
WO2014165788A1 (en) 2013-04-05 2014-10-09 The Procter & Gamble Company Personal care composition comprising a pre-emulsified formulation
WO2014165722A1 (en) 2013-04-05 2014-10-09 The Procter & Gamble Company Hair care composition comprising a pre-emulsified formulation
US9655821B2 (en) 2013-04-05 2017-05-23 The Procter & Gamble Company Personal care composition comprising a pre-emulsified formulation
US10123966B2 (en) 2013-05-16 2018-11-13 The Procter And Gamble Company Hair thickening compositions and methods of use
WO2014197427A2 (en) 2013-06-03 2014-12-11 R. J. Reynolds Tobacco Company Cosmetic compositions comprising tobacco seed-derived component
WO2014204662A1 (en) 2013-06-17 2014-12-24 The Gillette Company A glide member comprising low to no hygroscopic components for use with a razor
WO2015002812A1 (en) 2013-07-03 2015-01-08 The Procter & Gamble Company Shampoo composition comprising low viscosity emulsified silicone polymers
WO2015002811A1 (en) 2013-07-03 2015-01-08 The Procter & Gamble Company Shampoo composition comprising low viscosity silicone polymers
WO2015035150A1 (en) 2013-09-05 2015-03-12 The Procter & Gamble Company Scalp care composition
WO2015100122A1 (en) 2013-12-23 2015-07-02 Lubrizol Advanced Materials, Inc. Suspension and stability agent for antidandruff hair care compositions
WO2015148309A1 (en) 2014-03-26 2015-10-01 The Gillette Company Razor comprising a molded shaving aid composition comprising a thermally resilient sensate
WO2015164680A1 (en) 2014-04-24 2015-10-29 The Procter & Gamble Company Scalp care composition
WO2015164138A1 (en) 2014-04-25 2015-10-29 The Procter & Gamble Company Method of inhibiting copper deposition on hair
WO2015164137A1 (en) 2014-04-25 2015-10-29 The Procter & Gamble Company Method of inhibiting copper deposition on hair
EP2937112A1 (en) 2014-04-25 2015-10-28 The Procter and Gamble Company Method of inhibiting copper deposition on hair
WO2015164139A1 (en) 2014-04-25 2015-10-29 The Procter & Gamble Company Method of inhibiting copper deposition on hair
WO2015164140A1 (en) 2014-04-25 2015-10-29 The Procter & Gamble Company Shampoo composition comprising gel matrix and histidine
US9993419B2 (en) 2014-06-16 2018-06-12 The Procter & Gamble Company Method of treating hair with a concentrated conditioner
US10123963B2 (en) 2014-06-16 2018-11-13 The Procter And Gamble Company Method of treating hair with a concentrated conditioner
US9993420B2 (en) 2014-06-16 2018-06-12 The Procter & Gamble Company Method of treating hair with a concentrated conditioner
WO2015195738A1 (en) 2014-06-20 2015-12-23 The Procter & Gamble Company Stability of zinc pyrithione dispersions
WO2016049455A1 (en) 2014-09-26 2016-03-31 The Procter & Gamble Company Personal care compositions comprising malodor reduction compositions
US10113140B2 (en) 2014-09-26 2018-10-30 The Procter & Gamble Company Freshening compositions and devices comprising same
WO2016054451A1 (en) 2014-10-03 2016-04-07 The Procter & Gamble Company Method of achieving improved volume and combability using an anti-dandruff personal care composition comprising a pre-emulsified formulation
WO2016054450A1 (en) 2014-10-03 2016-04-07 The Procter & Gamble Company Method of improved volume and combability using personal care composition comprising a pre-emulsified formulation
WO2016090207A1 (en) 2014-12-05 2016-06-09 The Procter & Gamble Company Composition for hair frizz reduction
WO2016100466A1 (en) 2014-12-18 2016-06-23 Lubrizol Advanced Materials, Inc. Amphiphilic suspension and stability agent for antidandruff hair care compositions
US9993404B2 (en) 2015-01-15 2018-06-12 The Procter & Gamble Company Translucent hair conditioning composition
WO2016172410A1 (en) 2015-04-23 2016-10-27 The Procter & Gamble Company A method of achieving targeted delivery of a scalp cleansing composition and a conditioning shampoo composition
WO2016172412A1 (en) 2015-04-23 2016-10-27 The Procter & Gamble Company Method of achieving targeted delivery/application of hair
US10258548B2 (en) 2015-04-23 2019-04-16 The Procter And Gamble Company Hair care conditioning composition
WO2016191518A1 (en) 2015-05-28 2016-12-01 The Procter & Gamble Company A method of improving hair quality by improving scalp health
WO2017004282A1 (en) 2015-06-29 2017-01-05 Takasago Internation Corporation (Usa) Musk compositions and methods of use thereof
WO2017004281A1 (en) 2015-06-29 2017-01-05 Takasago International Corporation (Usa) Musk composition and methods of use thereof
WO2017087028A1 (en) 2015-11-17 2017-05-26 The Procter & Gamble Company A method of improving hair quality by improving scalp health
WO2017096156A1 (en) 2015-12-04 2017-06-08 The Procter & Gamble Company Composition for hair frizz reduction
WO2017096153A1 (en) 2015-12-04 2017-06-08 The Procter & Gamble Company Composition for hair frizz reduction
WO2017097817A1 (en) 2015-12-08 2017-06-15 Clariant International Ltd A shampoo composition comprising at least one oligoester ammonium salt
US10322072B2 (en) 2015-12-15 2019-06-18 The Procter And Gamble Company Method of treating hair
US10285925B2 (en) 2015-12-15 2019-05-14 The Procter & Gamble Company Method of treating hair
US10265251B2 (en) 2015-12-15 2019-04-23 The Procter And Gamble Company Method of treating hair
US10265255B2 (en) 2015-12-15 2019-04-23 The Procter And Gamble Company Method of treating hair
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US10294013B2 (en) 2015-12-21 2019-05-21 The Procter And Gamble Plaza Package to dispense a foaming composition
WO2017120151A1 (en) 2016-01-06 2017-07-13 The Procter & Gamble Company Methods of forming a slurry with microcapsules formed from phosphate esters and multivalent ions
WO2017152020A1 (en) 2016-03-03 2017-09-08 The Procter & Gamble Company Aerosol antidandruff composition
WO2017151848A1 (en) 2016-03-03 2017-09-08 The Procter & Gamble Company METHOD OF CLEANING HAIR USING A LOW pH HAIR CARE COMPOSITION
WO2017152018A1 (en) 2016-03-03 2017-09-08 The Procter & Gamble Company Personal care composition with zinc-containing layered material
WO2017165615A1 (en) 2016-03-24 2017-09-28 The Procter & Gamble Company Hair care compositions comprising malodor reduction compositions
WO2017189946A1 (en) 2016-04-29 2017-11-02 The Procter & Gamble Company Method of treating a hair disorder with n-hydroxypyridinones
WO2018002100A1 (en) 2016-06-29 2018-01-04 Clariant International Ltd Composition for inhibiting micro-organisms
WO2018005258A1 (en) 2016-06-30 2018-01-04 The Procter & Gamble Company Conditioner composition comprising a chelant
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WO2018034878A1 (en) 2016-08-18 2018-02-22 The Procter & Gamble Company Hair care compositions comprising metathesized unsaturated polyol esters
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WO2018095813A1 (en) 2016-11-28 2018-05-31 Clariant International Ltd Cosmetic composition comprising a cationic copolymer
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