WO2000049868A1 - Compositions antimicrobiennes au selenium - Google Patents

Compositions antimicrobiennes au selenium Download PDF

Info

Publication number
WO2000049868A1
WO2000049868A1 PCT/US2000/004727 US0004727W WO0049868A1 WO 2000049868 A1 WO2000049868 A1 WO 2000049868A1 US 0004727 W US0004727 W US 0004727W WO 0049868 A1 WO0049868 A1 WO 0049868A1
Authority
WO
WIPO (PCT)
Prior art keywords
hydrogen
group
combination
formulae
zinc pyrithione
Prior art date
Application number
PCT/US2000/004727
Other languages
English (en)
Inventor
Eugene F. Rothgery
George Polson
Rahim Hani
Original Assignee
Arch Chemicals, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Arch Chemicals, Inc. filed Critical Arch Chemicals, Inc.
Priority to AU32437/00A priority Critical patent/AU3243700A/en
Publication of WO2000049868A1 publication Critical patent/WO2000049868A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur

Definitions

  • the present invention relates to selected selenium compounds as novel compositions-of-matter. Furthermore, the present invention relates to antimicrobial compositions useful in soaps, shampoos, skin care medicaments as well as hard surface cleaning compositions and fabric care compositions that contain selected selenium compounds. And still further, the present invention relates to antidandruff shampoo compositions that contain selected selenium compounds as antidandruff agents.
  • Zinc pyrithone and selenium disulfide are both well known antidandruff agents that have been used for decades in a variety of commercial shampoos.
  • one aspect of the present invention is directed to antimicrobial compositions of formula (I):
  • Y-R is hydrogen or Y is an oxygen, sulfur, selenium or an NR' moiety, wherein N is nitrogen and R and R' are independently selected from hydrogen, substituted or unsubstituted hydrocarbon radicals having one to twenty carbon atoms; and metal salts thereof, either alone or in combination with zinc pyrithione or ketoconazole or mixtures thereof.
  • Another aspect of the present invention is directed to an antimicrobial composition
  • an antimicrobial composition comprising (a) a functional product selected from the group consisting soaps, shampoo or skin care medicaments, and further comprising (b) an antimicrobially effective amount of (i) at least one compound selected from the group consisting of the formulae (I), (II), (III) and (IV):
  • Y-R is hydrogen or Y is an oxygen, sulfur, selenium or an NR' moiety, wherein N is nitrogen and R and R' are independently selected from hydrogen, substituted or unsubstituted hydrocarbon radicals having 1 to 20 carbon atoms; and metal salts thereof;
  • each R" is either hydrogen or an alkyl group; either alone or in combination with (ii) zinc pyrithione, ketoconazole or mixtures there.
  • Still another aspect of the present invention is directed to an antidandruff shampoo that comprises (a) a shampoo base and (b) an effective antidandruff amount of (i) at least one compound selected from the group consisting of the formulae (I), (II), (III) and (IV) as defined above; either alone or in combination with (ii) zinc pyrithione, ketoconazole or mixtures thereof.
  • the present invention is directed to a hard surface cleaning composition, comprising (a) a cleaning solution and (b) an antimicrobially effective amount of (i) at least one compound selected from the group consisting of the formulae (I), (II), (III) and (IV) as defined above, either alone or in combination with (ii) zinc pyrithione, ketoconazole or mixtures thereof.
  • the present invention is directed to a fabric care composition, comprising (a) suitable carrier and (b) an antimicrobially effective amount of (i) at least one compound selected from the group consisting of the formulae (I), (II), (III) and (IV) as defined above, either alone or in combination with (ii) zinc pyrithione, ketoconazole or mixtures thereof.
  • hydrocarbon radicals for the R and R groups in the above formula (I) are aliphatic hydrocarbons having between 3 and 15 carbons, more preferably a straight chain hydrocarbon having between 5 and 10 carbons.
  • substituted hydrocarbon is intended to include substituents such as halogen such as chloro, iodo, fluoro or bromo, alkoxy such as methoxy, ethoxy, propoxy or butoxy, nitro, thio, and amino combinations thereof, and the like.
  • Illustrative hydrocarbon groups include n-octyl, 2,4,4-trimethylpentyl- 3,5,5-trimethylhexyl, combinations thereof, and the like.
  • Compounds of Formula (I) wherein Y is oxygen may be made by a process which comprises the steps of:
  • Compounds of Formula (I) wherein Y is nitrogen may be made by a process which comprises the steps of: (a) reacting 2,6-dichloropyridine N-oxide, a primary or secondary amine containing between 1 and 20 carbon atoms (such as dimethanolamine or triethanolamine) and a base (such as sodium hydroxide or potassium hydroxide), optionally in the presence of water or an organic solvent, at an elevated temperature to produce a corresponding 2-chloro-6-substituted-pyridine N-oxide and (b) reacting said 2-chloro-6-substituted-pyridine N-oxide with a selenium- containing base to produce the corresponding l-hydroxy-6-substituted-pyridine- 2-selenium compound.
  • Compounds of Formula (I) wherein Y is sulfur may be made by a process which comprises the following steps:
  • Compounds of Formula (I) wherein Y is selenium may be made by a process similar to where Y is sulfur except that a selenium compound having between 1 and 20 carbon atoms or combinations thereof is used instead of thiol compound in step (a).
  • reaction temperatures for steps (a) and (b) range between a temperature of about 25° C to about 150° C, preferably employing a reflux temperature of between about 70° C and about 90° C.
  • Total reaction time for the process of this invention can vary over a wide range, but is advantageously between 30 minutes and 5 hours for step (a) and between 30 minutes and 5 hours for step (b).
  • Suitable bases include alkali metal hydroxides such as sodium hydroxide or potassium hydroxide, alkaline earth metal hydroxides such as calcium or magnesium hydroxide, pyridine, triethylamine and other tertiary amine bases, potassium carbonate, "DABCO” amine catalyst (l,4-diazabicyclo(2.2.2)octane), "DBU” (1,8- diazabicyclo(5.4.0)undec-7-ene), "DBN” (l,5-diazabicyclo(4.3.0)non-5-ene, t- butyltetramethyl-guanidine, combinations thereof, and the like.
  • alkali metal hydroxides such as sodium hydroxide or potassium hydroxide
  • alkaline earth metal hydroxides such as calcium or magnesium hydroxide
  • pyridine triethylamine and other tertiary amine bases
  • potassium carbonate potassium carbonate
  • DBUCO alkaliazabicyclo(2.2.2)oct
  • Preferred bases for step (a) are anhydrous, granular or powdered sodium or potassium hydroxide
  • preferred bases for step (b) are concentrated aqueous solutions of sodium hydro selenide having a concentration of base of between about 10% and about 90% by weight based upon the weight of the solution.
  • the base is employed in at least an amount equal to the number of moles for each reactant, and a molar excess of base relative to each reactant can be employed as desired.
  • the reactions for making compounds of Formula (I) are suitably carried out in the presence of a solvent.
  • Suitable organic solvents include, for example, ether, and acetone, methylene chloride, benzene, toluene, pyridine, tetrahydrofuran (“THF”), acetonitrile, dimethylsulfoxide (“DMSO”), dimethylformamide (“DMF”), and combinations thereof.
  • THF tetrahydrofuran
  • acetonitrile dimethylsulfoxide
  • DMF dimethylformamide
  • a reactive solvent can be employed, if desired, for example by using an organic alcohol, e.g. isopropanol, or n-octanol, in an amount sufficient to provide the desired reactant and solvent characteristics.
  • the molar ratio of reactants for the processes of this invention can vary over a wide range, but is preferably between 10:1 and 1:10, more preferably between 2:1 and 1:2, most preferably about 1 :1.
  • Final shape of the compounds of formulae (I), (II), (III) or (IV) may be any desired shape for the desired antimicrobiocial application.
  • they may be either platelets, rods, needles, spheres and the like.
  • the particle size may be from submicron to several microns in the largest dimension, for example, 0.05-30 microns.
  • Particles distributions may be unimodal or multimodal within this range of 0.1 to 30 microns.
  • Compounds of formula (I) may be used as antimicrobial agents in paints, adhesives, coatings, elastomers, sealants, shampoo, skin care medicaments and metal-working fluids.
  • Suitable salts of the compounds of Formula (I) include amine salts, alkali metal salts and alkaline earth metal salts and the like.
  • An amine salt such as monoethanol amine (“MEN') is preferred.
  • the antimicrobial compositions of the present invention are directed to shampoos and skin care medicaments that contain an antimicrobially effective amount of at least compound of formulae (I), (II), (III), or (IV), alone or combination with zinc pyrithione ketoconazole or both.
  • antimicrobial effective amount is meant an amount sufficient to impart to the compositions resistance against microbial attack by fungi and/or bacteria.
  • an antidandruff effective amount of the active ingredients must be in the formulation.
  • antidandruff effective amount is meant an amount sufficient to treat a dandruff condition in humans.
  • the antimicrobial compounds are employed in the composition in a total amount of between 0.05 and about 10 weight percent, more preferably between about 0.1 and about 5 weight percent, based upon the total weight of the antimicrobial composition.
  • zinc pyrithione or ketoconazole or mixtures of the two are used in combination with one or more compounds of the Formulae (I), (II), (III) and (IV)
  • the relative amount of zinc pyrithione or ketoconazole or both may be from about 1 % to about 99%, preferably about 10-90%, by weight of the total combination of antimicrobial ingredients.
  • the antimicrobial soaps, shampoos and skin care medicaments of the present invention may contain any base medium ingredient commonly used in soaps, shampoos or skin care medicaments that is compatible with the antimicrobial agents described above.
  • compatible it is meant no adverse reaction or effect would occur by their combination.
  • Illustrative base medium ingredients include glycerine, aloe, surfactants such as dodecyl-benzene-sulfate ("DDBS"), water and other ingredients such as listed in the Examples below.
  • DDBS dodecyl-benzene-sulfate
  • the compositions of formulae (I), (II), (III) or (IV) may be useful additives in industrial fluids (e.g. metalworking fluids), paints, coatings, other personal care products (e.g.
  • hard surface cleaners may contain any cleaning solution commonly used in hard surface cleaners that are compatible with the antimicrobial agents of the present invention.
  • compatible it is meant no adverse reaction or effect would occur by their combination.
  • Illustrative cleaning solutions would include any commercially known powdered cleaner of the type used to clean kitchen counters, both tubs and the like with up to 10% by weight of the cleaner containing the antimicrobial agents of the present invention.
  • fabric care compositions may contain any carrier composition commonly used in fabric care compositions that are compatible with the antimicrobial agents of the present invention.
  • compatible it is meant no adverse reaction or effect will occur by their combination.
  • Illustrative carrier compositions would include solvent sand cleaners commonly used to remove stains from carpets, clothing and the like.
  • composition of the present invention are useful, in any of the variety of applications described herein, as disinfectants and preservatives, inn a liquid or spreadable form, alone or in combination with an inert carrier such as water, liquid hydrocarbons, ethanol, isopropanol and the like. They can be employed using conventional procedures to control bacteria and fungi in various substrates, and can be applied bacterial or fungal organism directly.
  • compositions of this invention may also be applied to the substrate to be protected by any of the conventional methods, including dipping, spraying or brushing.
  • the following examples further illustrate the present invention. All parts and percentages employed therein are by weight unless otherwise indicated.
  • An antidandruff shampoo composition can be made using deagglomerated particles of zinc pyrithione and one or more compounds of Formulae (I), (II), (III), or (IV) in combination with the following ingredients:
  • Component N
  • Component B Zinc Pyrithione (25% aqueous dispersion) 0.5%
  • Component D Triethanolamine lauryl sulfate, 40% 44.0%
  • Triethanolamine 99% 4.0%
  • the antidandruff shampoo composition can be made as follows: Component A is prepared by heating water to 70° C and dissolving the other two ingredients with stirring (about 1500 rpm). Component B is then added, and stirring continued for 5 minutes. Stirring speed is reduced to -300 RPM. Component C is melted in a separate container, and is added then to the A/B mixture. The heat is removed and component D is added while the mixture cools. The term "q.s.” refers to quantity sufficient.
  • Component A is prepared by heating water to 70° C and dissolving the other two ingredients with stirring (about 1500 rpm).
  • Component B is then added, and stirring continued for 5 minutes. Stirring speed is reduced to -300 RPM.
  • Component C is melted in a separate container, and is added then to the A/B mixture. The heat is removed and component D is added while the mixture cools.
  • the term "q.s.” refers to quantity sufficient.
  • EXAMPLE 2 Antidandruff Shampoo Formulation II
  • Another antidandruff shampoo composition may be made using zinc pyrithione and one or more compounds of Formulae (I), (II), (III) or (IV) in combination with the following ingredients:
  • Component B Di(hydrogenated) tallow phthalic acid amine 5.0%
  • Component D Citric Acid, 50% aq. Solution, or
  • the antidandruff shampoo composition can be made by having components A and B each mixed well in separate containers. Component A is heated to 165-170°F and component B is added. The mixture is stirred for 30 minutes. The mixture is then cooled to 120°F, and component C is added. The pH of the resulting mixture is adjusted to 5.0-6.2 with component D, and the viscosity is adjusted with component E.
  • An antidandruff shampoo and conditioner composition is made using needle and rod forms of zinc pyrithione and one or more compounds of Formulae (I), (II), (III) and (IV) in combination with the following ingredients:
  • Component B Di(hydrogenated) tallow phthalic acid amide 4.0%
  • Component C Preservative q.s.
  • Citric acid 50% aqueous solution
  • Component E Ammonium chloride q.s.
  • This antidandruff shampoo and conditioner composition can be made by first mixing components A and B in separate containers. Component A is heated to 165-170°F and component B is added. The mixture is stirred for 30 minutes. The mixture is then cooled to 120°F, and component C is added. The pH of the resulting mixture is adjusted to 5.0-6.2 with component D, and the viscosity is adjusted with component E.
  • EXAMPLE 4 Antidandruff Shampoo with Conditioner II
  • Another antidandruff shampoo and conditioner composition was made using needle and rod forms of zinc pyrithione and one or more compounds of Formulae (I), (II), (III) or
  • Zinc Pyrithione (25%> aqueous dispersion) 0.25% Compound(s) of Formulae (I), (II), (III) or (IV) 0.75%
  • Component B is a compound having Component B:
  • Component C Tricetylammonium chloride .50%
  • Component D Cocamide MEA 1.70%
  • the antidandruff shampoo and conditioner composition can be made as follows: Component A is prepared by heating water to 50%C and dispersing the guar hydroxypropyl trimonium chloride and the magnesium aluminum silicate with rapid agitation. The zinc pyrithione dispersion and compound of Formulae (I), (II), (III) or (IV) are added to this combination with stirring. The pH of component A is adjusted to 4.5-5.0 with component F. Both components of B are slowly added to component A, mixing well. The pH of the mixture is adjusted to 5.7-6.3 is heated to 70-75°C and blended with component C, mixing well. Both components of D are added to the hot mixture, and stirred well. The pH of the mixture is adjusted to 5.7-6.3 with component F. The mixture is cooled to 40-45°C, and component E is added with stirring. If desired, the viscosity of the product can be increased by adding 0.05-1 % sodium chloride.
  • An "extra body” antidandruff shampoo and conditioner composition can be made using needle and rod forms of zinc pyrithione in combination with the following ingredients: Component A:
  • Component B Methyl Paraben 0.30%
  • Component C Triethanolamine lauryl sulfate 20.0%
  • Citric Acid 50% aqueous solution q.s.
  • the antidandruff shampoo and conditioner composition can be made as follows: Component A is heated to 70°C. The ingredients of component B are added with good stirring until dissolved. The ingredients of component C are added to the mixture sequentially, and heated with mixing to 75°C. The mixture is cooled with stirring to 40°C, and components D and E are added with stirring. The pH of the final composition is adjusted to 4.7 with component F.
  • Component A is heated to 70°C.
  • the ingredients of component B are added with good stirring until dissolved.
  • the ingredients of component C are added to the mixture sequentially, and heated with mixing to 75°C.
  • the mixture is cooled with stirring to 40°C, and components D and E are added with stirring.
  • the pH of the final composition is adjusted to 4.7 with component F.
  • EXAMPLE 6 EXAMPLE 6:
  • An antidandruff shampoo formulation of EXAMPLE 1 can be made using one or more compounds of formulae (I), (II), (III) or (IV) in combination with both zinc pyrithione (0.25% by weight of the formulation) and ketoconazole (0.25% by weight of formulation) in stead of zinc pyrithione alone.
  • An antidandruff shampoo formulation of EXAMPLE 1 can be made using one or more compounds of formulae (I), (III), (III), or (IV) in combination with ketoconazole (0.5% by weight of the formulation) instead of zinc pyrithione.
  • deposition agents may be used instead of the guar hydroxypropyl trimonium chloride in Example 4.
  • deposition agents are generally cationic surfactant polymers materials and help deposit particulate active ingredients (e.g. the above-noted selenium compounds and zinc pyrithione, which are solid particulat ⁇ s but not ketoconazole which is soluble).
  • the level of such cationic surfactant/polyer is preferably from 0.01% to 10%, more preferable from 0.05% to 5%, more preferably 0.1% to 2% by weight of the shampoo formulations.
  • the cationic charge density of the deposition aid which is defined as the reciprocal of the molecular weight of a monomeric unit of the polymer containing 1 charge, is at least 0.1 meq/g, preferably above 0.8 or higher.
  • the cationic charge density should not exceed 4 meq/g, it is preferably less than 3 and more preferably less than 2 meq/g.
  • the charge density can be measured using conductimetric analysis and should be within the above limits at the desired pH of use, which will in general be from about 3 to 9 and preferably between 4 and 8.
  • Preferred disposition aids are cationic derivatives of guar gum and cationic polyacrylamides.
  • Suitable cationic derivatives of guar gum are JAGUAR C13S, which has a low degree of substitution of the cationic groups and high viscosity.
  • JAGUAR C15 having a moderate degree of substitution and a low viscosity
  • JAGUAR C17 high degree of substitution, high viscosity
  • JAGUAR C16 which hs a hydroxypropylated cationic guar derivative containing a low level of substitutent groups as well as cationic quaternary ammonium groups
  • JAGUAR 162 which is a high transparency, medium viscosity guar having a low degree of substitution.
  • cationic surfactants include quaternary ammonium hydroxides, e.g. tetramethylammonium hydroxide, alkyltrimethylammonium hydroxides wherein the alkyl group has from about 8 to 22 carbon atoms, for example octyltrimethylammonium hydroxide, hexadecyltrimethylammonium hydroxide, cetyltrimethylammonium hydroxide, octyldimethylbenzylammonium hydroxide, stearyldi-methylbenzylammonium hydroxide, dioctadecyldimethylammonium hydroxide, tallow trimethylammonium hydroxide, cocotrimethylammonium hydroxide, and the corresponding salts thereof, e.g., chlorides as well as cetylpyridinium hydroxide or salts thereof, e.g., chloride.
  • quaternary ammonium hydroxides e.g. tetramethylam

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne des composés de sélénium sélectionnés utilisés comme agents antimicrobiens dans des savons, des shampooings, des médicaments de soin pour la peau, des détergents de surfaces dures, et des compositions de traitement pour tissus.
PCT/US2000/004727 1999-02-25 2000-02-24 Compositions antimicrobiennes au selenium WO2000049868A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU32437/00A AU3243700A (en) 1999-02-25 2000-02-24 Selenium antimicrobial compositions

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US12170799P 1999-02-25 1999-02-25
US60/121,707 1999-02-25
US51087100A 2000-02-23 2000-02-23
US09/510,871 2000-02-23

Publications (1)

Publication Number Publication Date
WO2000049868A1 true WO2000049868A1 (fr) 2000-08-31

Family

ID=26819728

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2000/004727 WO2000049868A1 (fr) 1999-02-25 2000-02-24 Compositions antimicrobiennes au selenium

Country Status (2)

Country Link
AU (1) AU3243700A (fr)
WO (1) WO2000049868A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007008293A2 (fr) * 2005-05-24 2007-01-18 Selenium, Ltd. Forumulations biocides a base de selenium et procedes d'utilisation
US8236337B2 (en) 2005-05-24 2012-08-07 Selenium, Ltd. Anti-microbial orthodontic compositions and appliances and methods of production and use thereof
US9370187B2 (en) 2005-05-24 2016-06-21 Selenium, Ltd. Selenium-based biocidal formulations and methods of use thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3235455A (en) * 1962-02-09 1966-02-15 Procter & Gamble Synergistic antibacterial compositions
US4496559A (en) * 1981-09-02 1985-01-29 Olin Corporation 2-Selenopyridine-N-oxide derivatives and their use as fungicides and bactericides
US5104645A (en) * 1990-02-02 1992-04-14 The Proctor & Gamble Company Antidandruff shampoo compositions
US5854266A (en) * 1994-12-05 1998-12-29 Olin Corporation Synergistic antimicrobial composition pyrithione and alcohol

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3235455A (en) * 1962-02-09 1966-02-15 Procter & Gamble Synergistic antibacterial compositions
US4496559A (en) * 1981-09-02 1985-01-29 Olin Corporation 2-Selenopyridine-N-oxide derivatives and their use as fungicides and bactericides
US5104645A (en) * 1990-02-02 1992-04-14 The Proctor & Gamble Company Antidandruff shampoo compositions
US5854266A (en) * 1994-12-05 1998-12-29 Olin Corporation Synergistic antimicrobial composition pyrithione and alcohol

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007008293A2 (fr) * 2005-05-24 2007-01-18 Selenium, Ltd. Forumulations biocides a base de selenium et procedes d'utilisation
WO2007008293A3 (fr) * 2005-05-24 2007-03-08 Selenium Ltd Forumulations biocides a base de selenium et procedes d'utilisation
AU2006269657B2 (en) * 2005-05-24 2012-04-19 Selenbio, Inc. Selenium-based biocidal formulations and methods of use thereof
US8236337B2 (en) 2005-05-24 2012-08-07 Selenium, Ltd. Anti-microbial orthodontic compositions and appliances and methods of production and use thereof
US9370187B2 (en) 2005-05-24 2016-06-21 Selenium, Ltd. Selenium-based biocidal formulations and methods of use thereof

Also Published As

Publication number Publication date
AU3243700A (en) 2000-09-14

Similar Documents

Publication Publication Date Title
KR100395277B1 (ko) 살생물제로서의치환된피리딘-2-온및치환된피리딘-2-티온
JP5450942B2 (ja) 局所用抗菌組成物
KR20090018120A (ko) 항균 조성물
JP2009528439A5 (fr)
DE102013214081A1 (de) Neue aminosäuremodifizierte Siloxane, Verfahren zu ihrer Herstellung und Anwendung
JP2018530520A (ja) 抗菌性ポリマー
EP0498636B1 (fr) Composition cosmétique
JP2021503440A (ja) ヘアケア組成物
IE41913B1 (en) Shampoo compositions
EP1732973A1 (fr) Polymeres reticules contenant des matieres derivees de biomasse
US3890434A (en) Hair and antiseptic formulations containing adducts of bis-(2-pyridyl-1-oxide) disulfide
US4091113A (en) Randomly terminated capped polymers
WO1994014872A1 (fr) Polymere polycationique et agent polycationique bactericide/algicide
WO2000049868A1 (fr) Compositions antimicrobiennes au selenium
EP2899213A1 (fr) Polysaccharides modifiés, procédé pour leur production et leur utilisation
IL40284A (en) Adducts of di-) 2 - pyridyl - 1 - oxide (disulfide with salts of alkali metals - ore
JP2004537626A (ja) 四級化ポリアミドアミン類、その製法、対応する組成物、およびその使用
KR101216538B1 (ko) 폴리우루시올의 나노 수용액이 함유된 샴푸 조성물, 그의 제조방법 및 항 비듬 균 및 탈모방지의 용도
JP2016518467A (ja) アルコキシル化ポリアミンから調製されるポリマー
JPS597759B2 (ja) 水不溶性固体微粒子物質を安定に分散したシヤンプ−組成物
KR20160070063A (ko) 아연 피리티온 및 4차 암모늄 염을 함유한 항-비듬 조성물 및 모발 관리 제형
CN107847416B (zh) 分散的内酰胺
US6426435B1 (en) Substantive water-soluble bis-quaternary salts of cinnamidoalkylamines
US11471389B2 (en) Enhanced stability of zinc pyrithione in oxidative environments, such as scalp sebaceous fluid
EP3681461B1 (fr) Composition antimicrobienne

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AL AM AT AU AZ BA BB BG BR BY CA CH CN CR CU CZ DE DK DM EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT TZ UA UG UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

122 Ep: pct application non-entry in european phase