WO2000026146A1 - Nouveaux algicides - Google Patents

Nouveaux algicides Download PDF

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Publication number
WO2000026146A1
WO2000026146A1 PCT/EP1999/008367 EP9908367W WO0026146A1 WO 2000026146 A1 WO2000026146 A1 WO 2000026146A1 EP 9908367 W EP9908367 W EP 9908367W WO 0026146 A1 WO0026146 A1 WO 0026146A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition according
formula
quaternary ammonium
compounds
composition
Prior art date
Application number
PCT/EP1999/008367
Other languages
German (de)
English (en)
Inventor
Michael Bloch
Original Assignee
Trigon Chemie Gmbh
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 Trigon Chemie Gmbh filed Critical Trigon Chemie Gmbh
Priority to AU11591/00A priority Critical patent/AU1159100A/en
Publication of WO2000026146A1 publication Critical patent/WO2000026146A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/52—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities
    • C02F1/54—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities using organic material
    • C02F1/56—Macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment

Definitions

  • the invention relates to compositions for the disinfection of water which contain a polymeric quaternary ammonium compound as the active substance.
  • DE-A-26 00 466 and DE-A-34 23 703 describe methods for controlling algae in aqueous systems, a condensation product of tetramethylethylene diamine dihydrochloride and epichlorohydrin being used as the algicide.
  • DE-A-32 47 536 discloses algicidal condensates of diaminoalkanes and urea or epichlorohydrin. However, these condensates show an algicidal activity only in combination with heavy metal ions.
  • Belgian patent 895 685 describes the use of quaternary polymeric ammonium compounds as microbicides. These polymeric quaternary ammonium compounds are prepared by condensing urea with dialkylaminoethyl or propyl amines, an intermediate product being an N, N'-bis (dialkylaminoethyl or propyl) urea which is reacted with epichlorohydrin. The reaction product can then be reacted further with a tertiary amine or slide.
  • EP-A-0 059 978 describes the use of a quaternary ammonium composition in combination with water-soluble copper and / or silver salts which, as active ingredients, include, for example, poly (diallyldimethylammonium chloride), polyd, 4-bis (dimethylazonium) -7-oxanonylenedichloride) and polyd, 4-bis (dimethylazonium) -6-hydroxy-heptylene dichloride) contains.
  • GB-A-2 1 94 227 discloses the use of a polymeric cationic quaternary ammonium composition of the benzalkolium type together with a copper salt, a gelling agent and an oxidizing agent for controlling algae.
  • EP-A-0 203 892 describes the use of polymeric ammonium compositions for controlling microorganisms in water systems, the dimethylammonium groups of this composition being alternately separated by alkylene and dibenzyl groups.
  • algicidal compositions based on polymeric quaternary ammonium compounds have considerable disadvantages. So they only show sufficient effectiveness in connection with toxic heavy metal ions and / or they tend to foam or develop odors.
  • the object on which the present invention is based was therefore to produce new algicidal compounds which, on the one hand, have a high Have effectiveness and on the other hand are physiologically compatible and can be produced inexpensively.
  • the invention relates to a composition for the disinfection of water, containing a polymeric quaternary ammonium compound of the formula (I) as active substance:
  • R is each independently a C 1 -C 7 hydrocarbon group
  • n is a number from 2 to 1
  • y is a number from 1 0 to 500
  • X is an anion
  • polyquaternary compounds according to the invention show very good algistatic and algicidal activity. They are also physiologically safe and can be manufactured in a simple manner. Other advantages of the compounds are their insensitivity to temperature fluctuations and their stability to pH changes and water hardness.
  • the starting material for the preparation of the compounds used as active substances is a bis (N, N-dialkylaminoalkyl) urea of the formula (II)
  • Urea and dialkylaminoalkylamines are used as starting products for the preparation of the bis (N, N-dialkylaminoalkyl) ureas.
  • These raw materials are products that are technically manufactured in large quantities and are therefore available at low cost. Production takes place in a one-pot process, the only by-product being ammonia.
  • the subsequent condensation of the bis (N, N-dialkylaminoalkyl) ureas with dihaloalkanes is also easy to carry out, cf. e.g. DE-OS 29 24 230, production example 1.
  • the process as a whole does not require a great deal of technical, time or personnel expenditure and is therefore very economical from an economic point of view.
  • R is a hydrocarbon radical having 1 to 7 carbon atoms.
  • R is preferably methyl, ethyl or benzyl, with methyl being particularly preferred.
  • m and m 'in formula (I) can each independently represent a number from 2 to 4.
  • n 6 is particularly preferred.
  • y stands for the chain length of the polymer compound and generally ranges from 1 0 to 500, particularly preferably from 50 to 300. Most preferably y is a number from 1 00 to 1 50, which has a molecular weight of the compound of about 20 to Corresponds to 30 kd.
  • the anions used to charge balance the quaternary ammonium groups of the compound of formula (I) are preferably halide ions selected from the group consisting of Cl, Br and J. Chloride ions are particularly preferred.
  • the polymeric quaternary ammonium compound has the formula (III):
  • y is a number from 1 0 to 500
  • X is an anion, especially a halide ion.
  • the compound of the formula (III) is a poly [iminocarbonylimino-1,3-propanediyl (dimethyl-iminio) -1,6-hexanediyl (dimethyliminio) -1,3-propanediyl-dihalide], wherein the halide ion is in particular a chloride ion.
  • This substance is known from DE-OS 29 24 230 as a cosmetic hair care product. This makes their microbicidal activity all the more surprising, which is at least comparable to the activity of compounds currently used in practice.
  • the composition according to the invention is preferably essentially free of heavy metals. However, it can optionally contain an oxidizing agent, for example a peroxo compound such as sodium and potassium persulfate or peroxydisulfate or hydrogen peroxide or chlorine-containing compounds such as chloroisocyanuric acid or hypochlorite.
  • the composition according to the invention can contain other common additives such as conditioning agents, stabilizers, solubilizers, etc.
  • the compositions are preferably used in amounts of about 0.1 to 10 ppm, preferably 0.2 to 5 ppm, based on the amount of water to be treated.
  • the composition according to the invention can contain one or more of the polyquaternary ammonium compounds of the formula (I).
  • the composition can optionally also contain other microbicides, for example algicides and / or bactericidal active substances, e.g. B. Other q uaterna re polyammonium compounds, as required.
  • the algae were cultivated in flasks with growth medium of the composition given in Table 1.
  • Table 1 The algae were cultivated in flasks with growth medium of the composition given in Table 1.
  • the cultivation was carried out at 24 ⁇ 3 ° C under continuous lighting and magnetic stirring at 250 ⁇ 50 rpm.
  • the culture was diluted 1: 4 with fresh medium weekly.
  • the cell concentration was determined using an electronic particle counter after 1:10 dilution of the algae suspension with the physiological saline solution "Celloton" (AL system) and using an 80 ⁇ m capillary. 50 ml of culture with a cell concentration of 1.0 ⁇ 10 5 cells / ml were introduced for the test procedure. As a positive control 20 ppm CuSO 4 were used. No active substance was added to the negative control. Each determination was made in parallel.
  • the effect of the test substances on the algae growth was determined by comparing the areas A below the growth curves.
  • the percent inhibition I of cell growth in each experiment and for the reference substance (positive control) was calculated as follows:
  • a c area under the curve for the test substance at a given concentration
  • polyquaternary ammonium compounds of the formula (I) which have been prepared by condensation of bis (N, N-dimethylaminopropyl) urea and an ⁇ , ⁇ -dichloro C 2 -C 10 alkane have an algicidal activity. Furthermore, it can be seen that the optimum of the algicidal activity is achieved when 1,6-dichlorohexane is used for the condensation reaction.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Hydrology & Water Resources (AREA)
  • Engineering & Computer Science (AREA)
  • Environmental & Geological Engineering (AREA)
  • Water Supply & Treatment (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des compositions pour stériliser de l'eau, qui contiennent comme principe actif, un composé ammonium quaternaire polymère.
PCT/EP1999/008367 1998-10-30 1999-11-02 Nouveaux algicides WO2000026146A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU11591/00A AU1159100A (en) 1998-10-30 1999-11-02 New algaecides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19850164.1 1998-10-30
DE1998150164 DE19850164A1 (de) 1998-10-30 1998-10-30 Neue Algizide

Publications (1)

Publication Number Publication Date
WO2000026146A1 true WO2000026146A1 (fr) 2000-05-11

Family

ID=7886217

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1999/008367 WO2000026146A1 (fr) 1998-10-30 1999-11-02 Nouveaux algicides

Country Status (3)

Country Link
AU (1) AU1159100A (fr)
DE (1) DE19850164A1 (fr)
WO (1) WO2000026146A1 (fr)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5529700A (en) * 1995-09-27 1996-06-25 Laporte Water Technologies & Biochem, Inc. Algicidal or algistatic compositions containing quaternary ammonium polymers

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5529700A (en) * 1995-09-27 1996-06-25 Laporte Water Technologies & Biochem, Inc. Algicidal or algistatic compositions containing quaternary ammonium polymers

Also Published As

Publication number Publication date
AU1159100A (en) 2000-05-22
DE19850164A1 (de) 2000-05-04

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