Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
• • 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
  • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
  • A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants

Definitions

• ABSTRACT sulfosuccinic acid semi-esters of oxyalkylated polynuclear alkylphenols of the for mula in which R represents a group of the formula OC-CH CH-COOMe 0r OC-CH-CH -COOMe l i l (OX) represents oxyalkylene radicals, R represents an alkyl group having 6 to 14 carbon atoms, Y represents hydrogen or has the same meaning as that given for R n represents a number from 2 to 25, z represents a number from 1 to 9 and Me stands for hydrogen or an alkali metal, and their use as dispersing and wetting agents for sprayable powders or dispersable concentrates containing water-insoluble organic biocidal agents.
• biocidal agents are often used in the form of so-called spray powders.
• These spray powders are powdery preparations of biocidal agents which are applied in the form of aqueous suspensions. In order to permit easy application, the suspensions must have a good suspension and wetting property.
• the spray powders in general contain carrier substances such as aluminium or magnesium silicates or synthetic silicic acids and optionally adhesives and, in addition, wetting and dispersing agents.
• the content of active substance in the spray powders may vary within wide limits; it amounts in most cases to about 20 to 80 percent by weight.
• the proportion of wetting and dispersing agents in the spray powders is in general about 0.5 to 8 percent by weight.
• organic biocidal agents are, for example, chlorohyrocarbons such as DDT, Lindan, Chlordan, Aldrin, Dieldrin, Endrin and Toxaphen, and phosphoric acid esters such as Parathion, Methylparathion, Malathion, Trithion and Systox as well as carbamates such as Carbaryl and similar compounds.
• chlorohyrocarbons such as DDT, Lindan, Chlordan, Aldrin, Dieldrin, Endrin and Toxaphen
• phosphoric acid esters such as Parathion, Methylparathion, Malathion, Trithion and Systox as well as carbamates such as Carbaryl and similar compounds.
• the present invention provides sulfosuccinic acid semi-esters of oxalkylated polynuclear alkyl-phenols, a process for preparing them and their use as dispersing and wetting agents for water-insoluble organic biocidal agents.
• the sulfosuccinic acid semi-esters of oxalkylated polynuclear alkyl-phenols of the present invention are compounds of the general formula I in which R represents a group of the formula -OC-CH -CH-COOMe or -OCCHCH COOMe SO Me $O Me (OX) represents oxyalkylene radicals, in particular oxyethylene and/or oxypropylene, R1 represents a saturated, straight chain or branched alkyl group having 6 to 14 carbon atoms, Y represents hydrogen or has the same meaning as that given for R, n represents a number from 2 to 25, z represents a number from 1 to 9 and Me stands for hydrogen or an alkali metal.
• the present invention furthermore provides dispersable concentrates of water-insoluble organic biocidal agents which contain sulfosuccinic acid semi-esters of oxalkylated polynuclear alkyl-phenols of the formula I as dispersing or wetting agents.
• mono-alkyl-phenols of the formula OH 1 y are condensed with formaldehyde in a molar ratio of 2 1 to 10 9 according to known methods (ef.
• the novolak resins there may be used as mono-alkyl-phenols of the formula for example hexyl-, heptyl-, octyl-, nonyl-, dodecylor tetradecyl-phenol or mixtures of these alkyl-phenols, the alkyl groups optionally being straight chain or branched groups.
• formaldehyde in form of an aqueous solution or of para-formaldehyde may be used.
• the acid catalysts may be mineral acids such as sulfuric acid, phosphoric acid or, owing to the fact that it can be easily eliminated during removal of the water by distillation, preferably hydrochloric acid.
• the acids are used in a concentration of 0.1 to 5 percent by weight, referred to the alkyl-phenol.
• the condensation is effected at temperatures in the range of from about 20 to 150 C, preferably from 80 to C, suitably under an' atmosphere of nitrogen.
• the water present after the condensation is then removed by distillation to a residual content in the novolak resin of less than 0.5 percent by weight. This operation is carried out finally under reduced pressure of less than 50 Torr.
• the novolaks obtained constitute more or less brittle, clear, yellow-brown coloured resins in the form of big blocks. They are mixtures of polynuclear alkyl-phenols which are linked by methylene bridges. Their composition depends above all on the ratio of alkyl-phenol to formaldehyde.
• the oxalkylation of the novolak resins is carried out according to known methods with ethylene oxide or 1,2-propylene oxide or ethylene oxide and propylene oxide in the presence of alkaline catalysts at about 100 to 210 C, preferably at to C.
• alkaline catalysts there may be used above all alkali metal hydroxides such as potassium hydroxide or, preferably, sodium hydroxide, or alkali metal-alkoxides such as sodium methylate or sodium ethylate. These alkaline catalysts are preferably used in a concentration of 0.05 to 1.0 percent by weight, referred to the novolak resin.
• the oxalkylation may be effected without pressure or in pressure vessels and the alkylene oxide may be introduced either in gaseous or liquid form.
• the alkylene oxide is used in such an amount that 2 to 25 moles of alkylene oxide groups are introduced per each phenolic hydroxyl groups. It is preferred to use 3 to 15 moles of ethylene oxide per mole of starting alkyl-phenol.
• the reaction of the novolak oxalkylate with maleic acid anhydride to yield the maleic acid semi-ester is carried out by mixing the components and stirring them at about 20 to 100C, preferably at 40 to 80C, in the presence of alkalis, preferably alkali metal hydroxides.
• alkalis preferably alkali metal hydroxides.
• These alkaline catalysts are used in a concentration of about 0.05 to 1.0 percent by weight, referred to the novolak oxalkylates. Since maleic acid anhydride tends to sublimation, it is advantageous to carry out the reaction in pressure vessels under a pressure of about 0.2 to 1.0 atmosphere gauge of nitrogen or air and to ensure thorough mixing, because at the beginning the molten maleic acid anhydride can not easily be mixed with the novolak oxalkylates.
• the maleic acid anhydride may be used in such an amount that all novolak oxalkylate hydroxyl terminal groups or a part thereof, at least however one terminal hydroxyl
• Transformation of these maleic acid semi-ester compounds into the corresponding sulfo-succinic acid semi-esters is effected in an aqueous medium by reaction with water-soluble sulfites or hydrogen sulfites.
• the sulfites or hydrogen sulfites preferably alkali metal or alkaline earth metal sulfites -bisulfites or -pyrosulfites are used in quantities of about 1.0 to 1.5 mole, preferably 1.05 to 1.1 mole, calculated as sulfurous acid per maleic acid semi-ester group.
• the di-alkali metal sulfites are particularly suitable, since they lead to the formation of dialkali metal salts of the sulfosuccinic acid semi-esters.
• the quantity of water added during the reaction may amount to 50 to 85 percent by weight, referred to the total solution or mixture. It depends on the solubility of the sulfosuccinic acid semi-ester salts and on the viscosity of the solutions.
• the reaction temperatures are kept at about 20 to 100 C, preferably at 40 to 80 C.
• the sulfosuccinic acid semi-ester salts of the present invention may be applied optionally without purification directly in the form of their solutions.
• the aqueous solutions of the sulfosuccinic acid semi-ester salts may also be dehydrated according to known methods, for example by spray-drying. This spray drying may also be carried out in the presence of other components, for example pyrogenic silicic acid.
• the salts of the sulfosuccinic acid semi-esters of oxalkylated novolak resins are sticky to solid substances; they are excellent wetting and dispersing agents with moderate foam formation and are therefore particularly suitable for biocidal spray powders.
• the amount of wetting and dispersing agents may be in the range of 0.5 to 8 percent by weight.
• wetting power was carried out as follows: a glass beaker having a capacity of 500 ml (8 cm diameter) was filled with tap water of 20 C and a hardness of 12dH (German hardness) and 1 gram of the spray powder to be tested was strewn on the surface. The time which is required for wetting the powder is measured and indicated in seconds as wettingr time.
• Table IV Wetting and dispersing power of sulfosuccinic acid semi-esters of oxethylated trinuclear novolaks (Example Nos. 5 9) in spray powder formulations.
• Spray powder formulations product according to Example substances which are diflicult Suspension property in 7n Wetting power in seconds All'lllltl siliceous chalk silicic acid wetting and dispersing agent according to Example 2 Simazin siliceous chalk -l silicic acid wetting and dispersing agent according to lixamplc 2 ('aplan siliceous chalk l silicia acid wetting and dispersing agent according to lixaulplc 2.
• sulfosuccinic acid semi-esters of the formula I as dispersing and wetting agents in the preparation of spray powders on the basis of waterinsoluble organic biocidal agents is a preferred application of this sulfosuccinic acid semi-ester. ln addition thereto. these compounds are excellently suitable as dispersing and emulsifying agents also for other purposes, for example for preparing emulsion concentrates of water-insoluble organic biocidal agents.
• the amount of wetting and dispersing agents may be in the range of l to 30% by weight of the emulsion concentrate.
• the sulfosuccinic acid semi-esters may be used alone or with other, preferably non-ionogenic emulsifiers, for example the reaction products of ethyleneoxide with lipophilic compounds.
• emulsifiable concentrates of organic biocidal agents are intended to illustrate this use of the sulfosuccinic acid semi-esters of the present invention.
• R represents a group of the formula O Me Ol' SO Me (OX) represents oxyethylene, oxypropylene and mixture thereof, R represents a saturated straight chain or branched alkyl group having 6 to 14 carbon atoms, Y represents hydrogen or has the same meaning as that given for R, n represents a number from 2 to 25, 1 represents a number from 1 to 9 and Me stands for hydrogen or an alkali metal.
• OX O Me Ol' SO Me
• polynuclear compound of claim 1 having the formula 2 (oc u OK H (211 wherein R is selected from the group consisting of -0C-CH -CH-COONa SO Na 3 and 0C-CH-CH2-COONa S0 Na 3 Z is equal to 8 and (Z+l )'n is equal to 224.
• R is selected from the group consisting of 14 -OCCH -CH-CONa and -0C-CH-C1-; -CO0Na so Na Z is equal to 2 and (Z+1)'n is equal to 24.

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• Chemical & Material Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Organic Chemistry (AREA)
• General Health & Medical Sciences (AREA)
• Health & Medical Sciences (AREA)
• Pest Control & Pesticides (AREA)
• Toxicology (AREA)
• Engineering & Computer Science (AREA)
• Dentistry (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Plant Pathology (AREA)
• Agronomy & Crop Science (AREA)
• Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Phenolic Resins Or Amino Resins (AREA)

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Cited By (9)

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Citations (6)

• 0
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• 1972
  • 1972-06-15 ZA ZA724139A patent/ZA724139B/xx unknown
  • 1972-06-23 ES ES404187A patent/ES404187A1/es not_active Expired
  • 1972-06-23 NL NLAANVRAGE7208668,A patent/NL177686C/xx not_active IP Right Cessation
  • 1972-06-27 CH CH962972A patent/CH583183A5/xx not_active IP Right Cessation
  • 1972-06-28 AU AU43978/72A patent/AU473171B2/en not_active Expired
  • 1972-06-28 IL IL39778A patent/IL39778A/xx unknown
  • 1972-06-28 AT AT556372A patent/AT325021B/de not_active IP Right Cessation
  • 1972-06-28 JP JP6418572A patent/JPS5617339B1/ja active Pending
  • 1972-06-28 IT IT26371/72A patent/IT956933B/it active
  • 1972-06-28 DD DD164020A patent/DD99987A5/xx unknown
  • 1972-06-29 GB GB3051372A patent/GB1391358A/en not_active Expired
  • 1972-06-29 BR BR4257/72A patent/BR7204257D0/pt unknown
  • 1972-06-29 CA CA146,011A patent/CA1015767A/en not_active Expired
  • 1972-06-29 HU HUHO1494A patent/HU165058B/hu unknown
  • 1972-06-29 YU YU1722/72A patent/YU36923B/xx unknown
  • 1972-06-29 US US267512A patent/US3888828A/en not_active Expired - Lifetime
  • 1972-06-30 SU SU1808652A patent/SU439970A3/ru active
  • 1972-06-30 FR FR7223801A patent/FR2144415A5/fr not_active Expired
• 1980
  • 1980-07-15 JP JP55095778A patent/JPS5812241B2/ja not_active Expired

Patent Citations (6)

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