US3886277A - Methods of controlling dandruff using 5,7-dichloro-8-hydroxy quinoline - Google Patents
Methods of controlling dandruff using 5,7-dichloro-8-hydroxy quinoline Download PDFInfo
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- US3886277A US3886277A US359046A US35904673A US3886277A US 3886277 A US3886277 A US 3886277A US 359046 A US359046 A US 359046A US 35904673 A US35904673 A US 35904673A US 3886277 A US3886277 A US 3886277A
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- dichlor
- dandruff
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/006—Antidandruff preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/12—Preparations containing hair conditioners
Definitions
- ABSTRACT A method and composition for controlling dandruff on the human scalp using 5,7-diclhlor-8-hydroxy quinoline or a salt thereof.
- the present invention relates to a method and composition for controlling dandruff on the human scalp by 10 i TABLE 1 using 5,7-dichlor-8-hydroxy quinoline, or a salt thereof.
- ammonium bromide, organic metal compounds such as phenyl'mercury a t hydroxy line and the salts thereof.
- the salts qulnollnes
- s'lodmes'hydmxy with elements of the first, second and third main quinoline, or 5'ehlel"7-iodihe'8'hydroxy quinoline groups, and the second and fifth secondary groups of Py thiohes such as zpyridone thlohe'N'oxide 40 the periodic system are particularly advantageous.
- the P y the Zine Salt thereof preferred salts are those with calcium, bismuth, alumintrichlormethylmercapto-4-cyclohexene-l,2- ium and zinc.
- the aluminium salt is particularly precarboximide, dialkyl-polythio-ether-dicarbonic acids ferred. such as, for example, the disulphide of B-mercaptopro- These compounds meet all of the requirements for an pionic acid, and undecylenic acid-monoethanolamide. additive o agents e the Care of the hair, Whether y In Australian Pat. No.
- the numbers give the limiting dilution for growth inhibition, starting with a shampoo diluted 1:10 with water. Dilution of the shampoo was carried out immediately prior to the test.
- compositions of shampoos A and B are given in Table 11.
- the skin compatibility of the compounds according to the invention is very good.
- shampoos and hair treatments containing 2% of the active substance of the invention produced no sensitization.
- the compounds of the invention may be applied to the hair and scalp in any non-toxic pharmaceutically acceptable carrier, and in particular in compositions normally used for application to the hair such as shampoos, hair conditioners, hair tonics and hair creams.
- the detergent can be anionic, cationic or amphoteric.
- Anionic detergents include both soap and nonsoap detergents. Suitable soap detergents are the sodium, potassium, ammonium and alkanolammonium salts of higher fatty acids.
- the detergent acts as a wetting agent to suspend the treatment agent in the aqueous or alcoholic medium and as an agent to facili-, tate washing and rinsing.
- the treatment agent according to the invention can be used as follows: 5,7-dichlor-8-hydroxy quinoline, or a salt of this compound,'is incorporated into a shampoo formula.
- the head In the case of heavy dandruff attack, the head is washed with this product every third to fourth day. In nearly all cases, the dandruff has disappeared after the fourth or fifth washing.
- it is generally sufficient to wash with the dandruff shampoo in one to two weeks. In particularly obstinate cases, it is advisable to treat again, after washing, with a composition containing the treatment agent of the invention.
- the amount of the treatment agent incorporated into the shampoo or other hair treating composition used can be any amount effective for anti-dandruff control.
- the complete treatment consists of treating the hair twice a week for the first 2 weeks and once a week for the next 4 weeks.
- EXAMPLE 1 With a shampoo consisting of the hair of 20 persons suffering from heavy dandruff attack is washed every 3 to 4 days. After washing, the
- hair is well rinsed.
- 20 hair washings are carried out with the :same formula without the addition of 5,7-dichlor-8-hydroxy quinoline every third to fourth day.
- the heads washed with the shampoo containing the additive show slightly less dandruff than those washed with the shampoo without the additive.
- 16 of the 20 heads washed with the shampoo containing the additive are practically free of dandruff.
- the remaining four show substantially less dandruff than at the start of the test washing.
- the blank test made practically no improvement, i.e., several washings with a shampoo without the addition of 5,7-dichlor-8-hydroxy quinoline did not cause the dandruff to disappear, or even reduce it.
- EXAMPLE 2 The bismuth salt of 5,7-dichlor-8-hydroxy quinoline was used as the additive.
- the shampoo formula was the same as that in Example 1, but 2% of the additive is used (instead of 1% as in Example 1) and the amount of water added is reduced to 5.7%.
- Example 3 sodium-laurylalcohol-di-ethoxy ether sulfate 40.0% lauric acid diethanol amide 3.0% 5,7-dichlr-8-hydroxy-aluminum quinolate 1.0% remainder water 56.0%
- Example 4 triethanolamine-dodecyl benzene sulphonate 10.0% lauroyl-methylamino-triethanolamine acetate 8.0% 5,7dichlor-8-hydroxy-bismuth quinolate 1.5% remainder water 80.5%
- Example 5 stearic acid 4.0% glycol distearate 4.0% sodium-lauroyl-methyl-amino ethane sulphonate 4 l 0% sodium-dodecyl benzene sulphonate 12.5% 5,7-dichlor-8-hydroxy-zinc-quinolate 3.5% remainder water 35.0%
- compositions of Examples 3, 4 and 5 were used in the treatment of the hair of persons suffering from heavy dandruff attack following the procedures outlined above and similar results with respect to the control of dandruff were obtained.
- Composition 1 is a shampoo composition similar to Example 1 of the Australian patent containing 1.0% by weight of the diiodo additive of the Australian patent.
- Composition 2 is the same shampoo composition containing 1.0% by weight of the dichlor of applicants invention.
- Composition 3 is a hair lotion composition similar to Example 14 of the Australian patent containing 1.0% by weight of the diiodo additive of the Australian patent.
- Composition 4 is the same hair lotion composition containing 1.0% by weight of the dichlor additive of applicants invention.
- Deionized water to The models treated were selected according to the degree of dandruff attack, the emphasis being placed on medium and heavy attacks. In making the selection, care was taken to include in the tests only persons having dandruff uniformly distributed over the whole scalp. The selection was made in the presence of a dermatologist. No persons suffering from diseases of the scalp were included in the tests.
- each side was uniformly wetted and the so-called preliminary washing was carried out on each side. After the shampoo had been uniformly rinsed away, the main washing was carried out. Great care was taken to ensure that both sides received the same treatment as regards time of action, volume of rinse, and water temperature. After drying, each side was dressed without any after-treatment agent.
- a method of controlling the formation of visible dandruff comprising applying to the hair and scalp of humans affected therewith a composition comprising a non-toxic pharmaceutically acceptable carrier and 5,7- dichlor-8-hydroxy quinoline in an amount sufficient to provide effective anti-dandruff control.
- composition contains from 0.05 to 5.0% by weight of the 5,7- dichlor-S-hydroxy quinoline.
- composition contains from 0.01 to 5.0% by weight of the 5,7- dichlor-8-hydroxy quinoline.
- composition contains from 0.5 to 2.0% by weight of the 5,7-dichlor- 8-hydroxy quinoline.
- a method of controlling the formation of visible dandruff comprising shampooing the hair and scalp of humans affected therewith with an anionic, cationic or amphoteric detergent composition containing 5,7- dich1or'8-hydroxy quinoline in an amount sufficient to provide effective anti-dandruff control.
- composition contains from 0.05 to 5.0% by weight of the 5,7- dichlor-8-hydroxy quinoline.
- composition contains from 0.1 to 5.0% by weight of the 5,7-dichlor- S-hydroxy quinoline.
- composition contains from 0.5 to 2.0% by weight of the 5,7-dichlor- S-hydroxy quinoline.
Abstract
A method and composition for controlling dandruff on the human scalp using 5,7-dichlor-8-hydroxy quinoline or a salt thereof.
Description
United States Patent Randebrock et a1.
[ May 27, 1975 METHODS OF CONTROLLING DANDRUFF USING 5,7-DICIILORO-8-IIYDROXY QUINOLINE Inventors: Rudolf Randebrock,
Hamburg-Othmarschen; Volker Bollert, Hamburg; Heinz Lukesch, Hamburg-Sasel; Gertrud Muller, Hamburg; Ludwig Rappen, Diusburg-Meiderich; Friedhelm Galle, Duisberg-Hamborn, all of Germany Assignee: Hans Schwarzkopf GmbH,
Hamburg, Germany Filed: May 10, 1973 Appl. No.: 359,046
Related U.S. Application Data Continuation of Ser. No. 100,447, Dec. 21, 1970, abandoned, which is a continuation-in-part of Ser. No. 659,613, Aug. 10, 1967, abandoned.
Foreign Application Priority Data Feb. 14, 1967 Germany 40231 U.S. CI. 424/258; 252/106; 252/107;
424/245 Int. Cl. A6lk 27/00; AOln 9/22 [58] Field of Search 424/70, 245, 258, DIG. 4; 167/87 AD; 252/106, 107
OTHER PUBLICATIONS Wendlandt et al., Chem. Abst., Vol. 57, p. 9195, (1962).
Schraufstatter, Chem. Abst., Vol. 44, p. 8999, (1950). American Perfumer & Cosmetics, Vol. 78, No. 10, p. 60, Oct. 1963.
Bahal et al., Journal of Pharmaceutical Science, Vol. 50, No. 2, Feb. 1969, pp. 127430.
Primary Examiner-Albert T. Meyers Assistant Examiner-Allen J. Robinson [57] ABSTRACT A method and composition for controlling dandruff on the human scalp using 5,7-diclhlor-8-hydroxy quinoline or a salt thereof.
11 Claims, N0 Drawings This application is a continuation of application Ser.
compounds against dandruff shows that other assumptions for effective action against visible dandruff may be significant. For example, sodium selenite, which is effective against dandruff, exhibits scarcely any bacte- 100,447, filed Dee 21, 1970, which in tum is a 5 riostatic action. This may be seen in Table l, which continuation-in-part of application 659,613, shows the limit ofdilution in g/ml at which germ inhibifiled 1967 now abandoned tion is to be observed in an aqueous solution.
The present invention relates to a method and composition for controlling dandruff on the human scalp by 10 i TABLE 1 using 5,7-dichlor-8-hydroxy quinoline, or a salt thereof.
The human skin constantly renews itself, casting off S f l ureus chla alblcans parts of the old skm. These particles of skm, known as Oxford" dandruff, cannot be seen with the naked eye when the Sodium selenite 500 500 500 formation normal. In normal cases, the formation of 15 Cetyl Trimethyldandruff on the skin occurs practically invisibly. In Ammomum Bmmde 2 l5 8 many cases, however, especially on the skin of the scalp, the formation of dandruff takes place with foror plfrpose of compansoll Table 1 Shows the mation of large pieces which may be Seen with the tCllOStatlC action of cetyl-trlmethyl-ammomum bronaked eye and which, from the cosmetic point of view, g
etermmation of the limiting bacteriostatic action are regarded as extremely unpleasant. When the hair 15 was Carried out by the tube series dilution test combed the dandruff falls upon the clothmg, giving the Control of dandruff by the above mentioned mpresslon of a lack hyglene' Thus, one of the alms stances, which have scarcely any bacteriostatic action, in caring for the hair is to control the formation of visiis f tl ascribed to their k l i action, H ble dandruffever, accurate data in this connection has not hitherto Many agents have been suggested for the purpose. been available, and precise information regarding the For example, mention has been made of the use of submechanism of these compounds in combatting danstances exhibiting bacteriostatic and fungistatic properdruff attack Cannot be given. ties as agents for controlling dandruff. Such substances 0 It has now been found h to the invention, are, for example, phenols, resorcine, hexachlorophene, F among the large class 9 chemlcal Compounds or 2,2l hio bi di hl ph l carbanmdes such as mg bacteriostatic and fungistatic action, there are to be for example, 3,4,4'-trichlorosalicylic anilide, quaterl Certam whlch have Speclfic,
against dandruff 1n additlon to the said bacteriostatic nary ammonium compounds such as cetyl trlmethyl and fungistatic action.
ammonium bromide, organic metal compounds such These compounds are 5,7 dichlOr 8 hydr0Xy quino for example phenyl'mercury a t hydroxy line and the salts thereof. Among the salts, the salts qulnollnes Such for example s'lodmes'hydmxy with elements of the first, second and third main quinoline, or 5'ehlel"7-iodihe'8'hydroxy quinoline groups, and the second and fifth secondary groups of Py thiohes such as zpyridone thlohe'N'oxide 40 the periodic system are particularly advantageous. The P y the Zine Salt thereof, preferred salts are those with calcium, bismuth, alumintrichlormethylmercapto-4-cyclohexene-l,2- ium and zinc. The aluminium salt is particularly precarboximide, dialkyl-polythio-ether-dicarbonic acids ferred. such as, for example, the disulphide of B-mercaptopro- These compounds meet all of the requirements for an pionic acid, and undecylenic acid-monoethanolamide. additive o agents e the Care of the hair, Whether y In Australian Pat. No. 246,452 of August 2, 19 63, the be shampoospr halr treatmentsuse of 5,7-diiodo-8-hydroxy quinoline as a dandruff These requlrfiments are: controlling agent is described. Constant action after long storage, especially in the There was thought to be a connection b etween the presence of detergent substances such as are used in b cterial flora of the scal skin and the onset of visible Shampoos fe i l a p Substantivlty of the additive: on the scalp and hair, to dandruff Recent work 9 causes i l to ensure lasting effect between shampoos or treatments. appear as very doubtful, smce it has been impossible to Satisfactory Compatibility with the skin and, finally, demonstrate any clear differences between the bactewith an Substances used in making up shampoos and rial flora in a scalp skin with visible dandruff and one 5 hair treatments. with norma invisible dandruff. Thus the action of Retention of full bacteriostatic action after long stortain bacteriostatic and fungistatic substances cannot, in age and in the presence of detergent substances was the present state of the art, be explained simply by the demonstrated by the tube-series dilution test. The valsaid properties of these substances. The effective acues in Table II show a very satisfactory action by 5,7- tion of sulphur sulphur compounds, and l i dichlor-8-hydroxy quinoline and its salts in shampoos.
I TABLE ll Staphy- Staphy- Coryne- Escher- Pityro Candida lococclococcbact. ichia sporon albicans us us pseudo- Coli ovale aureus epiderdiphth mlS Shampoo no inhno inhno inhno inhno inhno inhdillsted ibition ibition ibition ibition ibition ibition According to Table III the action of the compounds 1 according to the invention are also not lost after 6 months storage at 40C.
TABLE III that practically all cultures appearing on the hairs were covered.
Ten hairs were used in the tests at all times. The hairs Staphy- Staphylococlococ' eus cus aureus epidermis Coryne Escherbact. ichia pseudo- Coli diphth.
Pityrosporan ovale Candida albicans Shampoo +2% 5 ,7- dichlor- S-hydroxy quinoline; freshly prepared; diluted 1 with water.
Shampoo B +2% 5,7- dichlor- 8- hyd roxy quinoline; stored 6 months at C; diluted l: 10 with water.
Shampoo A +2% bis muth salt of 5,7- dichlor- 8-hydroxy quinoline; freshly prepared; diluted 1:10 with water Shampoo A +2% bismuth salt of 5,7- dichlor- 8-hydroxy quiline; diluted 1:10 with water.*
"stored 6 months at 40C.
The numbers give the limiting dilution for growth inhibition, starting with a shampoo diluted 1:10 with water. Dilution of the shampoo was carried out immediately prior to the test. The
compositions of shampoos A and B are given in Table 11.
The enduring action of 5,7-dichlor 8-hydroxy quinoline and its salts over a period of time was demonstrated by the identifications of germs on hair. It was found that by taking ten individual hairs from a test subject, the same cultures were demonstrated as by taking hairs from the same test subject. Thus by taking about 10 hairs, it could be assumed with safety were cut with sterile shears at a maximum of 0.5 cm from the skin of the scalp, were transferred with a sterile pipette to a sterile tube, and were finally added to the nutrient medium. After incubating for 24 hours at 37C, sowing on blood-agar plates was carried out, these being again incubated at 37C for 24 hours. A qualitative determination of the cultures was then carried out. Table IV shows the results of these tests.
Rods (Dirt TABLE IV -C0ntinued Sample Sample Sample 3 Sample 24 Before Directly Hours After Hours Washing After Washing After Washing Washing Gemis) Test Subject Staph. Staph. Staph. Staph. 2 Washed with albus haem; albus haem; albus haem; albus; Shampoo A Staph. Staph. Staph. aureus Staph. with No epidennis epidermis haem; Staph. aureus haem; additive epidermis Staph.
epidermis Test Subject Staph. Staph. Staph. albus Staph. albus 3 Washed with albus haem; albus haem haem; Staph. haem; Staph. Shampoo A Gramnegaaureus haem; aureus haem; with No tive Rods Gramnegative Gramnegative additive (Dirt Germs) Rods (Dirt Rods (Dirt Genns) Germs) Test Subject Aerobacter Staph. Aerobacter Aerobacter 4 Washed with aero enes; citreus aero enes; aero enes; Shampoo A Stap epi- Stapfi. Staph. with No dermis epidermis epidermis additive Test Subject Bacillus Staph. albus Staph. albus Staph. albus 5 Washed with cereus; haem haem; Staph. haem; Shampoo A Staph. epidermis; Staph. epiwith No albus haem Pseudonomas dermis; additive Pseudonomas Test Subject Staph. albus Staph. albus Staph. albus 6 Washed with haem; Strept. haem haem Shampoo A anh. Addition of 2% Calcium Salt of 5,7- Dichlor-8- hj droxyquin- 0 me Test Subject Staph. albus; Staph. Staph. Staph. albus 7 Washed with Strept. anh.; albus albus haem Shampoo A Aerobacter haem haem Addition of aerogenes 2% Calcium Salt of 5,7- Dichlor-8- hydroxyquinoline Test Subject Staph. albus Staph. albus Staph. albus 8 Washed with haem; Esch. haem haem Shampoo A coli Addition of 2% Calcium Salt of 5,7- Dichlor-8- hydroxyquinoline Test Subject Staph. albus Staph. albus Staph. albus Staph. albus 9 Washed with haem; acrobe haem haem haem Shampoo A Actinomy- Addition of ceten 2% Calcium Salt of 5,7- Dichlor-S- hydroxyquinoline Test Subject Staph. Staph. Staph. Staph. albus l0 Wahsed albus haem; albus haem albus haem haem; Adhesive with Shampoo Adhesive spec. A 2% Calspec. cium Salt of 5,7-Dichlor- S-hydroxyquinoline Test Subject Staph. Staph. Staph. ll Washed albus haem; albus haem albus haem with Shampoo Gramnegative A 2% Calbacilli cium Salt of (Air Germ) 5,7-Dichlor- 8-hydroxyquinoline Test Subject Gramnegative Staph. Staph. Staph. l2 Washed bacilli albus haem albus haem albus haem with Shampoo (Dirt Germs) A 2% Cal- Phyllomanic cium Salt of Streptoco- 5.7-Dichlorccus Staph. B-hydroxyalb. haem; quinoline Sarcina lutea Test Subject Staph. Staph. Staph. Staph. l3 Washed albus haem; albus haem albus haem albus haem with Shampoo Bac.
TABLE IV Continued Sample Sample Sample 3 Sample 24 Before Directly Hours After Hours Washing After Washing After Washing Washing A 2% Calceret'i's cium Salt of 5,7-Dichlor- 8-hydroxyquinoline The composition of Shampoos A and B are shown in Table II.
Samples of hair were taken prior to washing, immediately after washing and three hours and 24 hours after washing. In the case of heads washed with shampoos containing the addition according to the invention of 5,7-dichlor-8-hydroxy quinoline, there occurred throughout a slower resettlement than in the case of the comparison washing without the additive of the invention.
The skin compatibility of the compounds according to the invention is very good. By means of the repeat-- ed-insult-patch-test it was proved that shampoos and hair treatments containing 2% of the active substance of the invention produced no sensitization.
The compounds of the invention may be applied to the hair and scalp in any non-toxic pharmaceutically acceptable carrier, and in particular in compositions normally used for application to the hair such as shampoos, hair conditioners, hair tonics and hair creams.
It is particularly advantageous to use the compounds in combination with a detergent. The detergent can be anionic, cationic or amphoteric. Anionic detergents include both soap and nonsoap detergents. Suitable soap detergents are the sodium, potassium, ammonium and alkanolammonium salts of higher fatty acids. When used in a detergent composition, the detergent acts as a wetting agent to suspend the treatment agent in the aqueous or alcoholic medium and as an agent to facili-, tate washing and rinsing.
Practical application of shampoos or hairtreatment agents containing the additive of the invention is as usual. In the case of heavy dandruff attack, the hair should be washed at intervals of 2 3 days. Washing of the hair may be followed by treatment with an additive containing treatment agent. Proof of the effectiveness of the substances of the invention is best obtained by controlled treatment of test subjects by the hairdresser. Particularly good results have been obtained by tests on one side only; after a few washings, these show the expert a clear distinction between the differently treated halves of the head.
The treatment agent according to the invention can be used as follows: 5,7-dichlor-8-hydroxy quinoline, or a salt of this compound,'is incorporated into a shampoo formula. In the case of heavy dandruff attack, the head is washed with this product every third to fourth day. In nearly all cases, the dandruff has disappeared after the fourth or fifth washing. In order to avoid the reoccurrence of dandruff, it is generally sufficient to wash with the dandruff shampoo in one to two weeks. In particularly obstinate cases, it is advisable to treat again, after washing, with a composition containing the treatment agent of the invention.
The amount of the treatment agent incorporated into the shampoo or other hair treating composition used can be any amount effective for anti-dandruff control.
Good results are obtained if from 0.01 to 5.0% by weight of the treatment agent are used, preferably 0.05 to 5.0%. Particularly good results are obtained when from 0.5 to 2.0% by weight of the treatment agent are 'used in the composition.
Preferably these should be used in amounts of from 5 to 20 grams of the treatment agent for each treatment, this amount usually being applied in two separate consecutive treatments. Preferably the complete treatment consists of treating the hair twice a week for the first 2 weeks and once a week for the next 4 weeks.
The following examples are given by way of describing typical usage of the anti-dandruff additive accord ing to'the invention.
EXAMPLE 1 With a shampoo consisting of the hair of 20 persons suffering from heavy dandruff attack is washed every 3 to 4 days. After washing, the
hair is well rinsed. By way of comparison, 20 hair washings are carried out with the :same formula without the addition of 5,7-dichlor-8-hydroxy quinoline every third to fourth day.
After the third washing, the heads washed with the shampoo containing the additive show slightly less dandruff than those washed with the shampoo without the additive. After five washings, 16 of the 20 heads washed with the shampoo containing the additive are practically free of dandruff. The remaining four show substantially less dandruff than at the start of the test washing. The blank test made practically no improvement, i.e., several washings with a shampoo without the addition of 5,7-dichlor-8-hydroxy quinoline did not cause the dandruff to disappear, or even reduce it. Of
the subjects treated with the additive-containing shampoo, a group of 8 then had their hair washed with the shampoo without the additive at intervals of 3 to 4 days, while another group of 8 persons had their hair washed again with the additive-containing shampoo at intervals of 3 to 4 days. After 5 to 10 washings, dandruff reoccurred in the 8 persons who had their hair washed with the formula without the additive, while the persons who had their hair washed with the shampoo containing the additive remained free of dandruff.
EXAMPLE 2 The bismuth salt of 5,7-dichlor-8-hydroxy quinoline was used as the additive. The shampoo formula was the same as that in Example 1, but 2% of the additive is used (instead of 1% as in Example 1) and the amount of water added is reduced to 5.7%.
Twenty persons exhibiting heavy dandruff attack had their hair washed on one side with the aforesaid additive-containing shampoo, and on the other side with the same formula without any additive. After four washings at intervals of 3 to 4 days, the side washed with the additive-containing dandruff shampoo showed a distinct improvement, the dandruff attack having receded. After eight washings, practically all of the sides of the heads washed with the additive-containing shampoo were free of dandruff, while the sides of the heads washed with the same formula without additive showed no improvement.
Example 3 sodium-laurylalcohol-di-ethoxy ether sulfate 40.0% lauric acid diethanol amide 3.0% 5,7-dichlr-8-hydroxy-aluminum quinolate 1.0% remainder water 56.0%
Example 4 triethanolamine-dodecyl benzene sulphonate 10.0% lauroyl-methylamino-triethanolamine acetate 8.0% 5,7dichlor-8-hydroxy-bismuth quinolate 1.5% remainder water 80.5%
Example 5 stearic acid 4.0% glycol distearate 4.0% sodium-lauroyl-methyl-amino ethane sulphonate 4 l 0% sodium-dodecyl benzene sulphonate 12.5% 5,7-dichlor-8-hydroxy-zinc-quinolate 3.5% remainder water 35.0%
The compositions of Examples 3, 4 and 5 were used in the treatment of the hair of persons suffering from heavy dandruff attack following the procedures outlined above and similar results with respect to the control of dandruff were obtained.
In all of the examples there was no indication of any toxic effect of the compositions on the scalps of the persons treated.
In order to illustrate the superiority of the treatment agents of this invention over known bacteriostatic agents, tests were made using the 5,7-diiodo-8-hydroxy quinoline compound disclosed in the Australian Pat. No. 246,452 referred to above for purposes of comparison.
Following the disclosure of the Australian patent, the 5,7-dichlor-8-hydroxy quinoline of applicants invention was used in a shampoo composition similar to Example 1 of the Australian patent, and a hair lotion composition similar to Example 14 of the Australian patent. The four compositions used for testing are set out in Table V below. Composition 1 is a shampoo composition similar to Example 1 of the Australian patent containing 1.0% by weight of the diiodo additive of the Australian patent. Composition 2 is the same shampoo composition containing 1.0% by weight of the dichlor of applicants invention. Composition 3 is a hair lotion composition similar to Example 14 of the Australian patent containing 1.0% by weight of the diiodo additive of the Australian patent. Composition 4 is the same hair lotion composition containing 1.0% by weight of the dichlor additive of applicants invention.
Deionized water to The models treated were selected according to the degree of dandruff attack, the emphasis being placed on medium and heavy attacks. In making the selection, care was taken to include in the tests only persons having dandruff uniformly distributed over the whole scalp. The selection was made in the presence of a dermatologist. No persons suffering from diseases of the scalp were included in the tests.
The persons tested had to undertake to refrain from using any hair care agents for a period of 8 weeks. They were not allowed to wash their hair for this period.
Independent appraisals were made by fourjudges before the hair was washed. A total of five stages of evaluation was possible:
XXX- XX- heavy dandruff attack medium dandruff attack mild dandruff attack dandruff no longer detected by person under test; isolated flakes still found by examiner O A complete freedom from dandruff In the valuation:
was assigned 3 points XXX XX was assigned 2 points X was assigned 1 point (X) was assigned 0.2 points 0 was assigned 0 points parting, after which the halves of the heads were washed with shampoo compositions 1 or 2.
The hair on each side was uniformly wetted and the so-called preliminary washing was carried out on each side. After the shampoo had been uniformly rinsed away, the main washing was carried out. Great care was taken to ensure that both sides received the same treatment as regards time of action, volume of rinse, and water temperature. After drying, each side was dressed without any after-treatment agent.
This washing of the hair on each side was carried out twice in the first 2 weeks and once in the next 4 weeks.
Fourteen days after the last treatment, all the hair on I the head was washed with a shampoo free of the active substance. Final appraisal was carried out 2 weeks later.
Comparison of hair lotions was carried out as follows: prior to the treatment, all the hair was washed with a shampoo free of the active substance. After rinsing and drying, the hair was parted in the middle and each side was treated with the same amount of hair lotion compositions 3 or 4. The treatment with the hair lotion was TABLE VI Dandruff Partly No Eliminated Eliminated Change 1 9 9 6 2 17 6 1 3 l l2 2 4 l9 In order to give additional emphasis to the results of this practical test, it should also be mentioned that the bactericidal and fungacidal action of the dichlor com pound II is considerably greater than that of the diiodo compound 1. The following figures show the concentration, in mg/ml, required to inhibit the growth of the micro-organisms indicated.
TABLE VI] Strept. pyrogenes 6 2 2.1 Strept. faecalis 99.2 8.6 Staph. aureaus 39.7 5.4 Escherichia coli 99 2 21.4 Asperg. niger 4 0 1.3
The above tests illustrate that the treatment agent of the invention exhibits unexpectedly superior effectiveness as a dandruff controlling agent over the additive of the Australian patent.
What we claim as our invention is:
l. A method of controlling the formation of visible dandruff comprising applying to the hair and scalp of humans affected therewith a composition comprising a non-toxic pharmaceutically acceptable carrier and 5,7- dichlor-8-hydroxy quinoline in an amount sufficient to provide effective anti-dandruff control.
2. The method of claim 1, in which the composition contains from 0.05 to 5.0% by weight of the 5,7- dichlor-S-hydroxy quinoline.
3. The method of claim 1 in which the composition contains from 0.01 to 5.0% by weight of the 5,7- dichlor-8-hydroxy quinoline.
4. The method of claim 1 in which the composition contains from 0.5 to 2.0% by weight of the 5,7-dichlor- 8-hydroxy quinoline.
5. A method of controlling the formation of visible dandruff comprising shampooing the hair and scalp of humans affected therewith with an anionic, cationic or amphoteric detergent composition containing 5,7- dich1or'8-hydroxy quinoline in an amount sufficient to provide effective anti-dandruff control.
6. The method of claim 5, in which the composition contains from 0.05 to 5.0% by weight of the 5,7- dichlor-8-hydroxy quinoline.
7. The method of claim 5 in which the composition contains from 0.1 to 5.0% by weight of the 5,7-dichlor- S-hydroxy quinoline.
8. The method of claim 5 in which the composition contains from 0.5 to 2.0% by weight of the 5,7-dichlor- S-hydroxy quinoline.
9. The method of claim 5 in which the hair and scalp of humans is shampooed with from 5 to 20 grams of the 5,7-dichlor-8-hydroxy quinoline.-
10. The method of claim 9 in which the 5 to 20 grams is applied in two separate consecutive treatments.
11. The method of claim 9 in which shampooing is conducted twice each week for 2 weeks, and once each week for the next 4 weeks.
Claims (11)
1. A METHOD OF CONTROLLING THE FORMATION OF VISIBLE DANDRUFF COMPRISING APPLYING TO THE HAIR AND A SCALP OF HUMANS AFFECTED THEREWITH A COMPOSITION COMPRISING A NON-TOXIC PHARMACEUTICALLY ACCEPTABLE CARRIER AND 5,7-DICHLOR-8-HYDROXY QUINOLINE IN AN AMOUNT SUFFICIENT TO PROVIDE EFFECTIVE ANTI-DANDRUFF CONTROL.
2. The method of claim 1, in which the composition contains from 0.05 to 5.0% by weight of the 5,7-dichlor-8-hydroxy quinoline.
3. The method of claim 1 in which the composition contains from 0.01 to 5.0% by weight of the 5,7-dichlor-8-hydroxy quinoline.
4. The method of claim 1 in which the composition contains from 0.5 to 2.0% by weight of the 5,7-dichlor-8-hydroxy quinoline.
5. A method of controlling the formation of visible dandruff comprising shampooing the hair and scalp of humans affected therewith with an anionic, cationic or amphoteric detergent composition containing 5,7-dichlor-8-hydroxy quinoline in an amount sufficient to provide effective anti-dandruff control.
6. The method of claim 5, in which the composition contains from 0.05 to 5.0% by weight of the 5,7-dichlor-8-hydroxy quinoline.
7. The method of claim 5 in which the composition contains from 0.1 to 5.0% by weight of the 5,7-dichlor-8-hydroxy quinoline.
8. The method of claim 5 in which the composition contains from 0.5 to 2.0% by weight of the 5,7-dichlor-8-hydroxy quinoline.
9. The method of claim 5 in which the hair and scalp of humans is shampooed with from 5 to 20 grams of the 5,7-dichlor-8-hydroxy quinoline.
10. The method of claim 9 in which the 5 to 20 grams is applied in two separate consecutive treatments.
11. The method of claim 9 in which shampooing is conducted twice each week for 2 weeks, and once each week for the next 4 weeks.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US359046A US3886277A (en) | 1967-02-14 | 1973-05-10 | Methods of controlling dandruff using 5,7-dichloro-8-hydroxy quinoline |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DESC040231 | 1967-02-14 | ||
US10044770A | 1970-12-21 | 1970-12-21 | |
US359046A US3886277A (en) | 1967-02-14 | 1973-05-10 | Methods of controlling dandruff using 5,7-dichloro-8-hydroxy quinoline |
Publications (1)
Publication Number | Publication Date |
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US3886277A true US3886277A (en) | 1975-05-27 |
Family
ID=27212359
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US359046A Expired - Lifetime US3886277A (en) | 1967-02-14 | 1973-05-10 | Methods of controlling dandruff using 5,7-dichloro-8-hydroxy quinoline |
Country Status (1)
Country | Link |
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US (1) | US3886277A (en) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0019970A1 (en) * | 1979-05-23 | 1980-12-10 | THE PROCTER & GAMBLE COMPANY | Conditioning shampoo |
US4496559A (en) * | 1981-09-02 | 1985-01-29 | Olin Corporation | 2-Selenopyridine-N-oxide derivatives and their use as fungicides and bactericides |
US4701322A (en) * | 1980-04-21 | 1987-10-20 | The Procter & Gamble Company | Conditioning shampoo |
FR2597343A1 (en) * | 1986-04-18 | 1987-10-23 | Egyt Gyogyszervegyeszeti Gyar | PHARMACEUTICAL COMPOSITION COMPRISING AN ORGANIC ZINC COMPLEX AND PROCESS FOR PREPARING THE ACTIVE PRODUCT. |
US5734029A (en) * | 1991-10-10 | 1998-03-31 | Henkel Corporation | Preparation of improved alkypolygloycoside surfactant mixtures |
US5972358A (en) * | 1998-01-20 | 1999-10-26 | Ethicon, Inc. | Low tack lotion, gels and creams |
US5997893A (en) * | 1998-01-20 | 1999-12-07 | Ethicon, Inc. | Alcohol based anti-microbial compositions with cosmetic appearance |
US6022551A (en) * | 1998-01-20 | 2000-02-08 | Ethicon, Inc. | Antimicrobial composition |
US6033676A (en) * | 1992-03-11 | 2000-03-07 | Joseph B. Taphorn | Treatment of scalp baldness with 8-hydroxyquinoline sulfate |
US6248343B1 (en) | 1998-01-20 | 2001-06-19 | Ethicon, Inc. | Therapeutic antimicrobial compositions |
CN105125913A (en) * | 2015-09-08 | 2015-12-09 | 桂林盛兴电子科技有限公司 | Externally-applied traditional Chinese medicine lotion for dandruff treatment and preparation method of externally-applied traditional Chinese medicine lotion for dandruff treatment |
CN105125912A (en) * | 2015-09-08 | 2015-12-09 | 桂林盛兴电子科技有限公司 | Externally-applied Chinese herbal medicine lotion for dandruff treatment and preparation method of externally-applied Chinese herbal medicine lotion for dandruff treatment |
WO2024045401A1 (en) * | 2022-08-30 | 2024-03-07 | 闽都创新实验室 | Crystal compound, preparation method, and use of same in x-ray direct detection and imaging |
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US2695881A (en) * | 1951-01-22 | 1954-11-30 | Monsanto Chemicals | Antiseptic soap composition |
US3100175A (en) * | 1960-07-15 | 1963-08-06 | Sandoz Ltd | Antiseptic composition |
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US2695881A (en) * | 1951-01-22 | 1954-11-30 | Monsanto Chemicals | Antiseptic soap composition |
US3100175A (en) * | 1960-07-15 | 1963-08-06 | Sandoz Ltd | Antiseptic composition |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0019970A1 (en) * | 1979-05-23 | 1980-12-10 | THE PROCTER & GAMBLE COMPANY | Conditioning shampoo |
US4701322A (en) * | 1980-04-21 | 1987-10-20 | The Procter & Gamble Company | Conditioning shampoo |
US4496559A (en) * | 1981-09-02 | 1985-01-29 | Olin Corporation | 2-Selenopyridine-N-oxide derivatives and their use as fungicides and bactericides |
FR2597343A1 (en) * | 1986-04-18 | 1987-10-23 | Egyt Gyogyszervegyeszeti Gyar | PHARMACEUTICAL COMPOSITION COMPRISING AN ORGANIC ZINC COMPLEX AND PROCESS FOR PREPARING THE ACTIVE PRODUCT. |
BE1001251A4 (en) * | 1986-04-18 | 1989-09-05 | Egyt Gyogyszervegyeszeti Gyar | Pharmaceutical composition containing organic complex zinc and method for preparing the active product. |
US5734029A (en) * | 1991-10-10 | 1998-03-31 | Henkel Corporation | Preparation of improved alkypolygloycoside surfactant mixtures |
US6033676A (en) * | 1992-03-11 | 2000-03-07 | Joseph B. Taphorn | Treatment of scalp baldness with 8-hydroxyquinoline sulfate |
US5997893A (en) * | 1998-01-20 | 1999-12-07 | Ethicon, Inc. | Alcohol based anti-microbial compositions with cosmetic appearance |
US6022551A (en) * | 1998-01-20 | 2000-02-08 | Ethicon, Inc. | Antimicrobial composition |
US5972358A (en) * | 1998-01-20 | 1999-10-26 | Ethicon, Inc. | Low tack lotion, gels and creams |
US6080416A (en) * | 1998-01-20 | 2000-06-27 | Ethicon, Inc. | Low tack lotion, gels and creams |
US6248343B1 (en) | 1998-01-20 | 2001-06-19 | Ethicon, Inc. | Therapeutic antimicrobial compositions |
CN105125913A (en) * | 2015-09-08 | 2015-12-09 | 桂林盛兴电子科技有限公司 | Externally-applied traditional Chinese medicine lotion for dandruff treatment and preparation method of externally-applied traditional Chinese medicine lotion for dandruff treatment |
CN105125912A (en) * | 2015-09-08 | 2015-12-09 | 桂林盛兴电子科技有限公司 | Externally-applied Chinese herbal medicine lotion for dandruff treatment and preparation method of externally-applied Chinese herbal medicine lotion for dandruff treatment |
WO2024045401A1 (en) * | 2022-08-30 | 2024-03-07 | 闽都创新实验室 | Crystal compound, preparation method, and use of same in x-ray direct detection and imaging |
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