DE3113872A1 - Suspensions of the zinc salt of 2-mercaptopyridine-N-oxide - Google Patents

Suspensions of the zinc salt of 2-mercaptopyridine-N-oxide

Info

Publication number
DE3113872A1
DE3113872A1 DE19813113872 DE3113872A DE3113872A1 DE 3113872 A1 DE3113872 A1 DE 3113872A1 DE 19813113872 DE19813113872 DE 19813113872 DE 3113872 A DE3113872 A DE 3113872A DE 3113872 A1 DE3113872 A1 DE 3113872A1
Authority
DE
Germany
Prior art keywords
zinc salt
oxide
suspensions
suspension
mercaptopyridine
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
DE19813113872
Other languages
German (de)
Inventor
Werner Dipl.-Chem. Dr. 6800 Mannheim Fickert
Manfred Dipl.-Chem. Dr. 6719 Kirchheim/Weinstraße Maurer
Winfried Dipl.-Chem. Dr. 6733 Hassloch Orth
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ruetgers Germany GmbH
Original Assignee
Ruetgerswerke AG
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 Ruetgerswerke AG filed Critical Ruetgerswerke AG
Priority to DE19813113872 priority Critical patent/DE3113872A1/en
Priority to IE820174A priority patent/IE820174L/en
Priority to ES509560A priority patent/ES509560A1/en
Priority to JP57055546A priority patent/JPS57176906A/en
Publication of DE3113872A1 publication Critical patent/DE3113872A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/044—Suspensions
    • 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
    • A61K8/4933—Cosmetics or similar toiletry 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
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/731—Cellulose; Quaternized cellulose derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • 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

Abstract

The stability of preparations which contain the zinc salt of 2-mercaptopyridine-N-oxide is improved by the use of non-ionic suspensions of this active compound. These non-ionic suspensions cannot be prepared with the aid of the non-ionic surfactants customarily used, but with the aid of non-ionic water-soluble cellulose derivatives.

Description

Suspensionen des Zinksalzes von 2-Merkaptopyridin-N-oxidSuspensions of the zinc salt of 2-mercaptopyridine N-oxide

Die Erfindung betrifft eine neue Suspensionsform des Zinksalzes von 2-Merkaptopyridin-N-Oxid sowie ein Verfahren zur Herstellung derartiger Suspensionen.The invention relates to a new suspension form of the zinc salt of 2-mercaptopyridine-N-oxide and a process for the preparation of such suspensions.

Das Zinksalz des 2-Merkaptopyridin-N-oxidsist unter der Bezeichnung Zinkpyrion(R) ein bekanntes Handelsprodukt.The zinc salt of 2-mercaptopyridine-N-oxide is under the designation Zinc pyrion (R) is a well-known commercial product.

Die Verbindung hat ein weites Wirkungspektrum gegen grampositive und gramnegative Bakterien. Darüber hinaus ist sie äußerst aktiv gegen Pilze und Hefen. Die Wirksamkeit des Zinkpyrions(R) ist pH-unabhängig.The compound has a wide spectrum of activity against gram-positive and gram negative bacteria. In addition, it is extremely active against fungi and yeasts. The effectiveness of the zinc pyrion (R) is pH-independent.

Das Produkt kommt als wäßrige, weiß-cremige Suspension in den Handel. Der Wirkstoffgehalt beträgt 48 %. Die Suspension erhält man durch Einwirkung von Scherkräften auf wasserhaltiges Zinkpyrion in Gegenwart von anionischen Tensiden. Dadurch entsteht eine auf lange Zeit (ca. 3 Monate) stabile Suspension mit einer durchschnittlichen Korngröße von 2 - 3zum. Sie wird vor allem im kosmetischen Bereich als Antischuppenmittel bei der Herstellung von Shampoos eingesetzt. Im technischen Bereich gelangen Suspensionen des Zinkpyrions(R) in den Gebieten zum Einsatz, bei denen Schutz vor Angriffen durch Bakterien, Pilze und Hefen geboten ist, z.B. zur Lagerkonservierung von Dispersionsfarben und -lacken, Acrylaten oder Styrol-Butadienpolymerisaten etc.The product is available on the market as an aqueous, creamy white suspension. The active ingredient content is 48%. The suspension is obtained by the action of Shear forces on hydrous zinc pyrion in the presence of anionic Surfactants. This creates a suspension that is stable for a long time (approx. 3 months) with an average grain size of 2 - 3 um. It is mainly used in cosmetic Area used as an anti-dandruff agent in the manufacture of shampoos. In the technical Suspensions of zinc pyrion (R) are used in the areas where which protection against attacks by bacteria, fungi and yeast is required, e.g. for Storage preservation of emulsion paints and varnishes, acrylates or styrene-butadiene polymers Etc.

Diese mit Hilfe von anionischen Tensiden hergestellten Suspensionen des Zinkpyrions(R)haben aber eine.Reihe von negativen Eigenschaften. So sind sie in vielen Fällen mit den in Shampoos verwendeten Bestandteilen (wie z.B. anorganischen Salzen) unverträglich und führen dort zu Ausflockungen und Auftrennung in einzelne, sich nicht mehr mischende Phasen.These suspensions produced with the aid of anionic surfactants of the zinc pyrion (R) have a number of negative properties. They're like that in many cases with the ingredients used in shampoos (such as inorganic Salts) are incompatible and lead to flocculation and separation into individual, phases that no longer mix.

Es bestand demnach das dringende Bedürfnis und die Aufgabe, eine Suspensionsform zu finden, die diese negativen Eigenschaften nicht hat und die sich bei der Herstellung von Antischuppenshampoos generell einsetzen läßt.There was therefore an urgent need and the task of a suspension form to find one that does not have these negative properties and that can be found in the manufacturing process can generally be used by anti-dandruff shampoos.

Diese Aufgabe wurde gelöst durch das Bereitstellen einer nichtionogenen Suspension des Zinksalzes von 2-Merkaptopyridin-N-oxid.This object was achieved by providing a nonionic Suspension of the zinc salt of 2-mercaptopyridine-N-oxide.

Eine derartige Suspension wird erhalten, indem man auf das wasserhaltige Zinksalz des 2-Merkaptopyridin-N-oxids nichtionogene Cellulosederivate einwirken läßt.Such a suspension is obtained by touching the water-containing Zinc salt of 2-mercaptopyridine-N-oxide act on non-ionic cellulose derivatives leaves.

Es wurde gefunden, daß es nicht gelingt, mit Hilfe der bekannten, üblicherweise verwendeten nichtionogenen Tenside wie z.B. den verschiedenen Polyäthylenglykolen, Fettsäuremonoglyceriden,Zuckerestern oder Fettsäurenalkylolamiden, stabile, nichtionogene Suspensionen des herzustellen.It has been found that it is not possible to use the known, commonly used non-ionic surfactants such as the various polyethylene glycols, Fatty acid monoglycerides, sugar esters or fatty acid alkylolamides, stable, nonionic To manufacture suspensions of the.

Uberraschenderweise ydingt dieser aber, wenn man das wasserhaltige Zinkpyrii mit geringen Mengen eines nichtionogenen, wasserlöslichen Cellulosederivates vermischt und starke Scherkräfte einwirken läßt. Als Cellulosederivate eignen sich vor allem Celluloseäther und zwar sowohl Alkylcellulosen als auch Hydroxyalkyläther sowie deren Mischäther, wie z.B. Methyl-, Hydroxyäthyl-, Hydropxypropyl, Methylhydroxyäthyl- oder Methylhydroxypropylcellulose. Diese Stoffe sind technisch bekannte Produkte, die als Tapetenkleister oder Verdickungsmittel Verwendung finden.Surprisingly, however, if you consider the water-containing Zinkpyrii with small amounts of a non-ionic, water-soluble cellulose derivative mixed and strong shear forces can act. As cellulose derivatives are suitable especially cellulose ethers, both alkyl celluloses and hydroxyalkyl ethers as well as their mixed ethers, such as methyl, hydroxyethyl, hydropxypropyl, methylhydroxyethyl or methyl hydroxypropyl cellulose. These substances are technically known products, which are used as wallpaper paste or thickening agents.

Umso überraschender ist der Effekt, daß aus einer pastösen Aufschlämmung aus Zinkpyrion(R) in etwa 35 - 70 Gew.- Wasser eine dünnflüssige Suspension entsteht, wenn ihr geringe Mengen eines oder mehrerer Celluloseäther zugesetzt werden.All the more surprising is the effect that from a pasty slurry zinc pyrion (R) in about 35 - 70 wt. water creates a thin suspension, if small amounts of one or more cellulose ethers are added to it.

Die Mengen des eingesetzten Cellulosederivates liegt bei 0,1 - 2,0 Gew.-%, bezogen auf das trockene Zinksalz, bevorzugt bei 0,5 - 0,6 Gew.-%.The amount of the cellulose derivative used is 0.1-2.0 % By weight, based on the dry zinc salt, preferably 0.5-0.6% by weight.

Es können auch größere Mengen an Cellulosederivat zugegeben werden, jedoch ergibt sich dann ein unerwünschter Verdickungseffekt, wodurch die Handhabung der Suspension erschwert wird.Larger amounts of cellulose derivative can also be added, however, there is then an undesirable thickening effect, which makes handling easier the suspension is made difficult.

Das Cellulosederivat kann zur wäßrigen Aufschlämmung des Zinkpyrions(R) zugegeben werden, wobei die Mischung intensiv gerührt wird, bis das Cellulosederivat gelöst ist.The cellulose derivative can be used as an aqueous suspension of zinc pyrion (R) be added, the mixture being stirred vigorously until the cellulose derivative is resolved.

Bevorzugt aber wird das Cellulosederivat in Wasser gelöst und diese Lösung mit der wäßrigen Aufschlämmung des Zinkpyrions gut gut vermischt. Zur Erzielung einer Lagerstabilität von etwa 3 Monaten muß diese Suspension noch starken Scherkräften ausgesetzt werden, etwa durch 15 - 20 minütige Behandlung mit einem Ultraturrax-Gerät C10 000 U/min).However, the cellulose derivative is preferably dissolved in water and this Solution well mixed with the aqueous suspension of zinc pyrion. To achieve a storage stability of about 3 months, this suspension must still have strong shear forces exposed, for example by 15-20 minutes of treatment with an Ultraturrax device C10 000 rpm).

Aus Gründen der Lagerstabilität und des Fließverhaltens hat sich die Herstellung einer Suspension mit etwa 40 Gew.-% Wirkstoffgehalt als besonders günstig erwiesen, obwohl wahlweise auch höhere oder niedrigere Wirkstoffkonzentrationen eingestellt werden können.For reasons of storage stability and flow behavior, the Production of a suspension with an active ingredient content of about 40% by weight is particularly favorable proven, although optionally higher or lower concentrations of the active ingredient can be adjusted.

Die so hergestellten Suspensionen zeigen die anfangs erwähnten negativen Eigenschaften der anionisch eingestellten Suspensionen nicht. Sie stellen Produkte dar, die sich ausgezeichnet mit Shampoos vertragen, auch wenn diese relativ große Mengen anorganischer Salze (z.B. Kochsalz ) enthalten.The suspensions produced in this way show the negatives mentioned at the beginning Properties of the anionically adjusted suspensions are not. They make products that go well with shampoos, even if they are relatively large Contains quantities of inorganic salts (e.g. common salt).

Zusätzlich kann man den erfindungsgemäßen Suspensionen wahlweise noch andere grenzflächenaktive Stoffe wie z.B.In addition, the suspensions according to the invention can optionally be used other surface-active substances such as

kationeEktive Substanzen zugeben, so daß die Grenzflächenaktivität wahlweise der übrigen Rezeptur angepaßt eingestellt werden kann.Add cationic active substances, so that the interfacial activity can optionally be adjusted to suit the rest of the recipe.

Beispiel 2,4 g Hydroxyäthylcellulose werden unter intensivem Rühren innerhalb 1/2 bis 2 h in 273 ml Wasser gelöst.Example 2.4 g of hydroxyethyl cellulose are stirred vigorously dissolved in 273 ml of water within 1/2 to 2 h.

Dann trägt man portionsweise unter weiterem Rühren 727 g Zinksalz des 2-Merkapto-pyridin-N-oxids (mit einem Wassergehalt von 45 Gew.-%) ein. Es entsteht ein gut rührbares Gemisch, das abschließend 15 min lang in einem Ultraturrax-Gerät mit 10 000 U/min homogenisiert wird.727 g of zinc salt are then carried in portions with continued stirring of 2-mercapto-pyridine-N-oxide (with a water content of 45% by weight). It arises a well-stirrable mixture, which is then used for 15 minutes in an Ultraturrax device is homogenized at 10,000 rpm.

Die resultierende nichtionogene Suspension ist gut fließfähig und etwa 3 Monate lang lagerstabil.The resulting non-ionic suspension is easy to flow and Storage stable for about 3 months.

Claims (6)

Patentansprüche 1. Nichtionogene Suspension des Zinksalzes von 2-Merkaptopyridin-N-oxid.Claims 1. Nonionic suspension of the zinc salt of 2-mercaptopyridine-N-oxide. 2. Verfahren zur Herstellung der nichtionogenen Suspension des Zinksalzes von 2-Merkapto pyridin -N-oxid, d a d u r c h g e k e n n z e i c h n e t, daß man auf das wasserhaltige Zinksalz des 2-Merkaptopyrydin-N-Oxids nichtionogene wasserlösliche Cellulosederivate einwirken läßt.2. Process for the preparation of the non-ionic suspension of the zinc salt of 2-mercapto pyridine -N-oxide, d u r c h e k e n n n z e i c h n e t that one on the water-containing zinc salt of 2-mercaptopyrydine-N-oxide non-ionic water-soluble Cellulose derivatives can act. 3. Verfahren nach Anspruch 2, da du r c h g e k e n nz e i c h n e t, daß die Herstellung der Suspension unter Einwirkung starker Scherkräfte erfolgt.3. The method according to claim 2, since you r c h g e k e n nz e i c h n e t that the preparation of the suspension takes place under the action of strong shear forces. 4. Verfahren nach Ansprüchen 2 und 3, d a d u r c h g e -k e n n z e i c h n e t, daß als Cellulosederivate nichtionogene wasserlösliche Celluloseäther verwendet werden.4. The method according to claims 2 and 3, d a d u r c h g e -k e n n z E i c h n e t that the cellulose derivatives are nonionic, water-soluble cellulose ethers be used. 5. Verfahren nach Ansprüchen 2 - 4, d a d u r c h g e -k e n n z e i c h n e t, daß die Cellulosederivate in Mengen von 0,1 - 2,0 Gew.-%, bezogen auf das trockene Zinksalz, eingesetzt werden.5. The method according to claims 2-4, d a d u r c h g e -k e n n z e i c h n e t that the cellulose derivatives in amounts of 0.1-2.0% by weight, based on the dry zinc salt, can be used. 6. Verfahren nach Ansprüchen 2 - 5, d a d u r c h g e -k e n n z e i c h n e t, daß die Cellulosederivate in Mengen von 0,5 - 0,6 Gewichts-%, bezogen auf das trockene Zinksalz, eingesetzt werden.6. The method according to claims 2-5, d a d u r c h g e -k e n n z e i c h n e t that the cellulose derivatives in amounts of 0.5-0.6% by weight, based on the dry zinc salt.
DE19813113872 1981-04-06 1981-04-06 Suspensions of the zinc salt of 2-mercaptopyridine-N-oxide Withdrawn DE3113872A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
DE19813113872 DE3113872A1 (en) 1981-04-06 1981-04-06 Suspensions of the zinc salt of 2-mercaptopyridine-N-oxide
IE820174A IE820174L (en) 1981-04-06 1982-01-27 Suspension of the zinc salt of 2-mercapto-pyridine-n-oxide
ES509560A ES509560A1 (en) 1981-04-06 1982-02-12 Suspensions of the zinc salt of 2-mercaptopyridine-N-oxide
JP57055546A JPS57176906A (en) 1981-04-06 1982-04-05 Nonionic suspension of zinc salt of 2-mercaptopyridine-n-oxide and manufacture

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19813113872 DE3113872A1 (en) 1981-04-06 1981-04-06 Suspensions of the zinc salt of 2-mercaptopyridine-N-oxide

Publications (1)

Publication Number Publication Date
DE3113872A1 true DE3113872A1 (en) 1982-10-21

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ID=6129487

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DE19813113872 Withdrawn DE3113872A1 (en) 1981-04-06 1981-04-06 Suspensions of the zinc salt of 2-mercaptopyridine-N-oxide

Country Status (4)

Country Link
JP (1) JPS57176906A (en)
DE (1) DE3113872A1 (en)
ES (1) ES509560A1 (en)
IE (1) IE820174L (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0173259A2 (en) * 1984-08-29 1986-03-05 Kao Corporation Antimicrobial suspensions and antimicrobial hair treatment compositions

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5865210A (en) * 1981-09-14 1983-04-18 アムウエイ・コ−ポレイシヨン Dandruff preventive cream rinse conditioner
JPH0816046B2 (en) * 1987-03-09 1996-02-21 信越化学工業株式会社 Raw material for cosmetics

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0173259A2 (en) * 1984-08-29 1986-03-05 Kao Corporation Antimicrobial suspensions and antimicrobial hair treatment compositions
EP0173259A3 (en) * 1984-08-29 1986-12-30 Kao Corporation Antimicrobial suspensions and antimicrobial hair treatment compositions

Also Published As

Publication number Publication date
ES509560A1 (en) 1983-02-01
JPS57176906A (en) 1982-10-30
IE820174L (en) 1982-10-06

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