MXPA97004072A - Derivatives of succinic acid and its comotensioacti use - Google Patents

Abstract

The present invention relates to a compound of the formula (I): characterized in that one of R1 and R2 in the succinic acid portion is C6 to C22 alkenyl or alkyl and the other is hydrogen, R3 is a hydrocarbyl polyhydroxy radical; hydrogen, C1 to C22 hydrocarbyl, or R4 is independently as defined above for R3, R5 is a group: -NR3R4, where R3 and R4 are independently as defined above, or R5 is a group: -O. (AO) n.R6, where: AO is an alkylene oxide residue, n is from 1 to 200, and R6 is hydrogen, C1 to C22 hydrocarbyl, or R6 is a group: (R1H) C.CO.NR3R4, (R2H) .C.CO. where R1, R2, R3 and R4 are independently as defined above, or R5 is a group: -NR7R8, where: R7 is hydrogen, C1 to C22 hydrocarbyl, and R8 is C1 to C22 hydrocarbyl, or NR7R8 is a pyrrolidino, piperidino, morpholino, piperazino or a N- (C1 to C6 alkyl) piperazino group, or -NR7R8 is a group of the formula -NH. (AO) n.R9, where AO and n are as defined in the foregoing and R9 is a C1 to C22 hydrocarbyl group, or -NR7R8 is a group of the formula NH. (AO) p.CH2CH2.OR10, where AO is as defined above, p is from 0 to 200, particularly from 0 to 100, and R10 is a hydrocarbyl of C1 to C22, or R10 is a group: (R1H) .C.CO.NR3R4, (R2H) .C.CO. where R1, R2, R3 and R4 are independently as defined above

Description

DERIVATIVES OF SUCCINIC ACID AND ITS USE AS SURFACTANTS DESCRIPTION OF THE INVENTION This invention relates to surfactants and in particular to novel surfactants based on substituted succinic acid derivatives and to the use of these surfactants particularly as adjuvants in agrochemical formulations and as dispersants and / or emulsifiers in agrochemicals, as dispersants for pigments, especially in aqueous dispersions, as emulsifiers in the emulsion polymerization, as surfactants in household detergents, particularly heavy duty laundry liquids, especially non-aqueous heavy duty laundry liquids and other applications. In recent years there has been an increasing desire to replace well-established surfactants with materials of increased biodegradability. However, there is great practical difficulty in contemplating alternatives for excellently functioning substances, which have maintained an important position in the market for several decades. EP 0107199 B and published PCT Application No. WO 94/00508 A ^ describe surfactants based on alkylene oxide esters and amides of the substituted alkyl or alkenyl succinic acid. This invention is based on the discovery of substituted amides or amide esters of the acids. alkenylsuccinic, particularly where the amide group is a glucamide group. These compounds have particular utility as surfactants and / or adjuvants in agrochemical formulations; as dispersants for pigments, for example in aqueous dispersions of pigments, especially TiC > 2, particularly for use in paints; and as surfactants in laundry formulations, especially in heavy-duty laundry formulations. This invention therefore provides compounds of the formula (I): (R ^ .C.CO.R5 wherein one of R1 and R2 in the succinic acid portion is alkenyl or Cg to C alkyl; and the other is hydrogen; R3 is a hydrocarbyl polyhydroxy radical; R 4 is hydrogen, C-, C22-hydrocarbyl, particularly C alquilo to C20 alkyl, C7 to C12 alkyl, C2 to C20 hydroxy-substituted alkyl, eg, ethanolyl (2-hydroxyethyl), or R4 is independently as defined in the above for R3; R5 is a group: -NR3R4, wherein R3 and R4 are independently as defined above; or R5 is a group: -0. (A0) n.R6, where: AO is an alkylene oxide, particularly an ethylene oxide residue; n is from 1 to 200, particularly from 2 to 100 (and since it is an average number it can not be a whole number); and R6 is hydrogen, C- ^ to C22 hydrocarbyl / particularly C- ^ to C2Q alkyl, especially C-j_ to Cg alkyl such as methyl, ethyl, propyl or butyl; or R ^ is a group: I (R ^ .C.CO. wherein R1, R2, R3 and R4 are independently as defined above; or R5 is a group: -NR7R8, wherein: R * 7 is hydrogen, hydrocarbyl of C-, C22 ', particularly alkyl of C- to C2Q, especially alkyl of CL to Cg such as methyl, ethyl, propyl or butyl; R8 is hydrocarbyl of C- ^ to c22 'particularly alkyl of C-j_ to C20, especially C-L to Cg alkyl such as methyl, ethyl, propyl or butyl; or -NR7R8 is a pyrrolidino, piperidino, morpholino, piperazino or a N- (C-, Cg-alkyl) piperazino group; or -NR7R8 is a group of the formula -NH. (AO) n.R9, where AO and n are as defined in the above and R9 is a hydrocarbyl group of C- ^ to C22, particularly an alkyl group; or -NR7R8 is a group of the formula -NH. (AO) .CH2CH2.OR10, where AO is as defined in the above; p is from 0 to 200, particularly from 0 to 100; and R10 is a hydrocarbyl of C- ^ to C22 particularly C-j ^ to C20 alkyl / especially C-L to Cg alkyl, such as methyl, ethyl, propyl or butyl; or R10 is a group: . { R ^ .C.CO. where R1, R2, R3 and R4 are independently as defined in the foregoing.

The following subgroups of the compounds of the formula (I) form specific aspects of the invention: 3"(ta) (F ^ Hí.C.CO.NFTR (R2H) .C.CO.NR3R4 where R1, R2, R3 and r4 are independently as defined above and the respective groups -NR3R4 are desirably, but not necessarily the same. 3"4 (Ib) (R1H) .C.CO.NR R (R2H) .C.CO.O (AO) _. R6 where R1, R2, R3, R4, AO, n and R6 are as defined in the foregoing.

(Ic) (RH) .C.CO.NR3R * I (R2H) .C.CO.O (AO) n.CO.C. (HR2) t. { R'H) .C.CO.NR3R4 where R1, R, NR R4, AO and n are as defined above and the respective groups R! / R2 and -NR R4 are desirably, but not necessarily the same.

(R2H) .C.CO.NH. (AO) n.R9 where R1, R2, R3, R, AO, n and R9 are as defined in the above. (le) (R?) .CO.NR3R4 (R2H) .C.CO.NH. (AO) _ .CH, CH5.NH.CO.C. (HR2) (RH) .C.CO.NR3R4 where R1, R2, R3, R4, AO and p are as defined above and the respective groups R! / R2 and -NR3R4 are desirably, but not necessarily the same. (| f) (R1H) .C.CO.NR 33 «R4 (R2H.C.CO.NR7RB where R1, R2, R3, R, R7 and R8 are as defined in the foregoing.

Among the compounds of the invention, those in which the alkenyl group R! / R is an alkenyl or Cg a ^ IQ > They are especially desirable. Similarly, compounds where the group R 1 or R 2 is an alkenyl group, are more desirable than those where the group is alkyl. The compounds wherein the group R1 or R2 is an alkenyl group, particularly a CQ to C18 alkenyl group of a specific aspect of the invention. It is desirable that the alkyl or alkenyl group or R! / R2 of the compounds of the invention have linear chains. Where the chain is not linear it is desirable that it has a total of two and preferably only one chain or branched chains on average. Preferably, the entire molecule comprises mostly three branched chains in total in all the present alkyl and alkenyl groups. The group R3 is a hydrocarbyl polyhydroxy radical, particularly one having a straight chain carbon of 4 to 7 carbon atoms and at least three hydroxyl groups directly attached to the carbon atom chain. The group may include substituents, in particular alkoxy groups, for example by etherification of additional hydroxyl groups or polyalkylene oxide chains, but the group desirably includes at least three free hydroxyl groups including such hydroxyl groups in substituents of the basic chain. Particularly R3 is an open chain tetrathol, pentylitol, hexitol or heptitol group or an anhydrous derivative of such group. Especially advantageous, R3 is the residue of, or a residue derived from, a reducing sugar, particularly a monosaccharide such as glucose or fructose, a disaccharide such as maltose or palitosa from a higher oligosaccharide. Where R3 is the residue of, or a residue derived from, a monosaccharide, the group or residue derived from the saccharide will usually be present as an open chain material. In the compounds of this invention, the R3 group is present as or as part of the hydrophilic. In this way, it will usually be advantageous if the hydrophilicity of this group is not properly reduced. The open chain form of such groups is typically most of the hydrophilic form and thus will usually be the desired form. Groups that include internal cyclic ether functionality, however, can be used, if desired and can be obtained inadvertently, if the synthetic route exposes the group to relatively higher temperatures or other conditions, which promote etherification. Where R3 is the residue of, or a residue derived from an oligosaccharide which can be considered as an open chain monosaccharide derivative or residue group with a saccharide or oligosaccharide substituent. Particularly useful R3 groups are glycosous derivatives and are of the formula: -CH2- (CHOH) 4 CH2OH, for example, that correspond to glucose, mannose or galactose residues. In this case the group -NR3R4 is of the formula: -NR4. CH2 (CHOH) 4 CH2OH and the group is conveniently called a glycine group and the corresponding amides can be called glycolides. Most commonly the R3 group will be derived from glucose and the corresponding amine and the amides are called glucamines and glucamides. R 4 can be hydrogen, hydrocarbyl or independently a group as defined for R. When R3 is hydrocarbyl, it will usually be either a short chain for example an alkyl group of C-L to Cg, particularly a methyl, ethyl, propyl or butyl group, or a hydroxyalkyl group such as an ethanolyl (2-hydroxyethyl) group. Alternatively, it may be a long chain group, which may act as an additional hydrophobe such as an alkyl group of CQ to C18 or an aralkyl group of C7 to C12. When R4 is a group as defined for R, it can act as an additional hydrophilic. These possibilities open the opportunities to form the hydrophilicity or hydrophobicity of the molecule for specific, suitable end uses. The group -NR3R4 can be considered as the residue of the amine H.NR3R4 [this amine is used in the typical synthesis of compounds of the formula (I) - see the following]. The amines of the formula H.NR3R4, where R4 is a sugar residue, can conveniently be made from reduced sugars by a reductive amination reaction, followed, if necessary, by alkylation (or reductive alkylation) to replace the R4 group in the amine primary H2NR4. The alkylene oxide group AO is typically a group of the formula: - (CmH mO) - where m is typically 2, 3 or 4, desirably 2 or 3, ie a group of ethylene oxide or propylene oxide, and it can represent different groups below the alkylene oxide chain. Generally, it is desirable that the chain is a homopolymeric ethylene oxide chain. However, the ceidene may be a homopolymer chain of propylene glycol residues or a random or block copolymer chain containing both ethylene glycol and propylene glycol residues. The chain length of the polyalkylene oxide group, when present, i.e. the value of the parameter n or p, will generally be chosen to provide the desired properties in the intended product. Typically, where the polyalkylene oxide chain is a polyethylene glycol chain, it will usually have from 1 to 100, more usually from 3 to 50, which correspond very roughly to the chains derived from PEG 50 to PEG 2000, the ethylene glycol residues and where there is a Polyoxypropylene chain will usually have from 1 to 50 propylene glycol residues. Where the chain is a block copolymer or random copolymer of ethylene and propylene glycol residues, the length of the chosen chain will typically correspond to the above ranges, but numerically according to the proportion of the ethylene and propylene glycol residues in the chain. Of course, the numerical values of the numbers of periodic units in the polyoxyalkylene chain are average values. As is common for surfactants containing a polyoxyalkylene chain, the higher the proportion of ethylene glycol residues and the longer the polyethylene glycol chain and the more hydrophilic the product. When, in formula (I), R6 is H or hydrocarbyl, particularly alkyl, if R6e is H, the products tend to be relatively more hydrophilic and if it is a hydrocarbyl, particularly an alkyl group, relatively less hydrophilic. Where R ^ is a relatively long chain group, for example an alkyl group of Cg +, then this group will tend to act as a second hydrophobe. The group R6 will be chosen according to the desired general properties of the compound at the desired end of the application used. The compounds of the invention can react a reactive precursor, typically an ester of a corresponding substituted succinic acid with an alcohol of the formula R1LOH (as defined in the following), with an amine of the formula H.NR3R4, where R3 and R4 are as defined above in a molar ratio corresponding to the number of amide functions in the final product and eliminating the alcohol R ^^ OH generated, typically by distillation . As applied to the compounds of the formulas (la) to (If) of specific syntheses described in the following. The compounds of the invention of the formula (la) can be made by reacting one mole of a diester: (RlH) .C.CO.OR11 (R 0.C.CO.OR where R1 and R2 are as defined above for formula (la) and R x is a lower alkyl group, particularly a C ^ to C4 alkyl, for example an ethyl, butyl or, and especially a methyl group, with two moles of amine: N.NR3R4, where R3 and R4 are as defined above for formula (la). The diester intermediate can be made by esterifying a corresponding alkyl or alkenyl succinic anhydride with an alcohol R1J-OH (where R11 is as defined above), especially methanol. The esterification can be conveniently carried out by one or two methods: i Alcohol R1: LOH is added to the anhydride and the mixture is typically stirred between 20 minutes and 2 hours, typically at moderately elevated temperatures, for example 40 to 120 ° C . A catalytic amount of acid such as sulfuric acid is then added and the mixture is heated, typically to a temperature reaction mixture of 80 to 150 ° C, particularly 100 to 120 ° C, where the alcohol is methanol and alcohol and water, from the esterification reaction, removed by distillation. The fresh alcohol is gradually added to maintain the volume of the reaction mixture and to direct the reaction to completion. Typically, the reaction is completed in 1 to 3 hours. The usually liquid diester product can be recovered by distilling off the excess alcohol, cooling the reaction mixture, neutralizing the acid catalyst, for example with sodium acid carbonate and removing the insoluble salts by filtration. ii Alcohol R1: 1-OH is added to the anhydride together with a catalytic amount of acid such as sulfuric acid. The reaction mixture is then typically heated to a temperature reaction mixture of 80 to 150 ° C, particularly 100 to 120 ° C, where the alcohol is methanol, and alcohol and water, of the esterification reaction, is removed by distillation. The fresh alcohol is added gradually to maintain the volume of the reaction mixture and to direct the reaction to completion. Typically, the reaction is complete from 1 to 3 hours. The usually liquid diester product can be recovered by distilling off the excess alcohol, cooling the reaction mixture, neutralizing the acid catalyst, for example with sodium hydrogen carbonate and removing the insoluble salts by filtration. The compounds of the formula (Ib) can be made by: i by reacting one mole of a compound: I (R2H) .C.CO.O. < AO) rvR, wherein R1, R2, AO, n and R6 are as defined in the above for formula (Ib), and R11 is as defined above, with one mole of amine: H.NR3R4, where R3 and R4 are as they were defined in the above for formula (Ib): or ii reacting one mole of a compound: I (R ^ .C-CO.OR11 where R1, R2, R3, R4 are as defined above for formula (Ib), and R11 is as defined above, with one mole of an oxide or derivative of alkylene: HO. (AO) n.R6, where AO, n and R6 are as defined in the above for formula (Ib). In the sequence i, the alkyl / (polyalkylene oxide) bis-ester intermediate can be made by reacting one mole of corresponding α? [Alkenyl or alkenylsuccinic anhydride with one mole of corresponding polyalkylene oxide (which can be crowned at one end ) to form a mono- (polyethylene oxide) ester followed by esterification with excess of alcohol R1: LOH. In sequence ii, the initial amide / ester material can be reacted with one mole of di-R11 ester of the alkyl or alkenylsuccinic acid corresponding: with one mole of amine H.NR3R4. Sequence i is preferred because it minimizes the possibility of forming diamide salt or diamine amide amine during the preparation of the intermediate. The compounds of the formula (le) can be made by reacting one mole of a compound: (R1H) .C.CO.OR11 where R1, R2, AO and n are as defined in the above for the formula (le), and R11 is as defined in the above, with two moles of amine: H.NR3R4, where R3 and R4 are as defined in the above for the formula (le). The bis (ester of succinic acid) polyalkylene oxide intermediate can be made to react one mole of corresponding polyalkylene hydroxy oxide (polyoxy-alkylene glycol) with two moles of corresponding alkyl or alkenylsuccinic anhydride by esterification with excess of alcohol R1: LOH. The compounds of the formula (Id) can be made by reacting one mole of a compound: (R1H) .C.CO.ORn (R2H) .C.CO.NH. (AO &nt; n.R9 where R1, R2, AO, n and R9 are as defined above for the formula (Id) and R11 is as defined above, with one mole of amine: H.NR3R4, where R3 and R4 are as defined in the above for the formula (Id). The initial ester / amide material can be made by reacting one mole of the corresponding di-R11 ester of the corresponding alkyl or alkenyl succinic acid with one mole of amine: NH2. (AO) n.R9, where AO, n and R9 are as defined in the above. The compounds of the formula (le) can be made by reacting one mole of a compound: 1 where R1, R, AO and p are as defined in • previous for the formula (le) and R11 is as defined in the above, with two moles of amine: H.NR3R4, where R3 and R4 are as defined in the above for the formula (le). The bis-amide / diester intermediate of polyoxyalkylene diamine can be made by reacting one mole of amine: NH2. (AO) .CH2CH2.NH2 with two moles of the di-R11 ester of the corresponding alkyl or alkenylsuccinic acid. The compounds of the formula (If) can be made by reacting one mole of a compound: (R CCO.OR'1 (RH) .C.CO.NR7R8 where R1, R2, R7 and R8 are as defined above for the formula (If) and R11 is as defined above, with an amine : H.NR R4, where R3 and R4 are as defined above for the formula (If) The ester / amide intermediate can be made by reacting one mole of the corresponding di-R11 ester of the corresponding alkenyl succinic acid with one mole of amine: H.NR7R8 Typically, in amidation reations, the amide reaction product is favored, such that the by-product R ^ OH alcohol does not generally need to be removed to activate the reaction towards the term. The alcohol will usually be removed, for example by distillation, to purify the desired diamide product, generally the amidation reactions proceed under relatively mild conditions, for example by heating at a temperature of 50 to 150 ° C, particularly 90 to 130 ° C, and be pure or in solution in a solvent or suitable diluent such as monopropylene glycol or a suitable liquid polyethylene glycol (PEG) such as PEG 200. It was not found necessary to use a catalyst for this reaction, but the catalysts usually accelerate the reaction. Suitable catalysts include alkoxides, particularly alkali metal alkoxides such as sodium methoxide and transition metal compounds such as tertiary butyl titanate (TBT) and zirconium butoxide.

The reactions between a precursor anhydride and the hydroxylic reagents such as an alcohol, polyalkylene glycol or an end-capped polyalkylene glycol can be carried out easily, with or without catalysts bringing the hydroxylic reagent into contact with the alkyl or alkenyl succinic anhydride. The reaction typically occurs at temperatures below 200 ° C and still below 100 ° C. The reagents will usually be used in at least about stoichiometric proportions. Particularly where the stoichiometric proportions are used, another purification usually does not appear to be necessary, but may be carried out if desired. The reactions of the monocarboxylic acid intermediates with alcohol R1: LOH (typically used in a molar excess) to generate the lower alkyl ester intermediates can be carried out in a convenient manner, for example using an acid catalyst which can be sulfuric, toluenesulfonic acid or a phosphonic acid. Phosphonic acids can be particularly useful after neutralization, they can be a useful component of detergent compositions, which include the surfactants of this invention. The products of the invention are typically a mixture of isomers corresponding to the two directions of opening of the anhydride ring during synthesis. It has been noted that the alkenyl or alkyl chain appears to have a minor steric effect on the ratio of isomer to isomer ratio which is typically about 60:40., the main isomer that is produced from nucleophilic attack in the anhydride carbonyl group removed from the alkenyl or alkyl group (probably due to steric hindrance). The precursors of the alkenyl succinic anhydride can be produced by the reaction of the maleic anhydride with an olefin having from 6 to 22, particularly from 8 to 18 carbon atoms, preferably with an excess, for example an excess of 50 to 200% of olefin at a temperature in the range of 150 to 400 ° C and preferably 180 to 250 ° C and removing excess olefin, for example by distillation, which is suitably carried out under vacuum. The catalyst is not necessary, but it is preferred that an antioxidant be present. These anhydrides are well-known commercial materials. In the alkenyl succinic anhydrides prepared as described above, the double bond is usually placed in the 2-position on the alkenyl substituent. To manufacture the products where the group R 1 or R 2 is an alkyl group, then any of the unsaturated products can be hydrogenated or, and preferably, the intermediate alkenyl succinic anhydride can be hydrogenated to give an alkylsuccinic anhydride.

Typically, the hydrogenation of the anhydride is carried out on a hydrogenation catalyst such as Raney nickel or a Pd / C catalyst. Temperatures of 15 to 100 ° C and pressures of up to 200 absolute bars can be used and, if desired, a solvent can be present. For example, the hydrogenation reaction in an alkenyl succinic anhydride can be carried out at 20 ° C at a pressure of 1 bar of H2 using 5% w / w of the Pd / C catalyst for a period of for example 6 to 24 hours. The compounds according to the invention have emulsification and wetting properties and dispersibility. These properties make the compounds of the invention suitable for use as surfactants in agrochemical formulations. In addition, in agrochemical formulations it can act as adjuvants, for example with herbicides such as glyphosate and sulfosate, fungicides such as Iprodione, Carbendazym and Propionazole, insecticides, acaricides and plant growth regulating formulations. Accordingly, the invention includes agrochemical formulations which include, in addition to at least one agrochemically active component, at least one compound of the invention as surfactants and / or adjuvants; and the invention further includes the use of the compounds of this invention as surfactants and / or adjuvants in agrochemical formulations. Generally, when used in agrochemical formulations, the compounds of the invention will typically be used at a concentration of 1 to 30% based on the formulation when used as surfactants, for example to disperse the agrochemical or agrochemicals and when used as adjuvants. , typically a concentration of 5 to 60% will be used based on the concentrated formulations and 100% on or as components for the addition to tank mixes. Other conventional components may be included in such formulations, such as one or more oils, by »Example mineral oils, vegetable oils and alkylated vegetable oils, which are typically alkyl mono-esters of C- ^ to Cg of vegetable oil fatty acids; solvents and / or diluents such as ethylene and / or propylene glycol or low molecular weight alcohols, which act to solubilize the formulation and / or reduce viscosities and / or to avoid or reduce dilution problems, for example the formation of gels; and other surfactants which may be anionic surfactants, cationic surfactants or nonionic surfactants such as alcohol alkoxylates, usually ethoxylates, or alkylphenolalkoxylates, usually ethoxylates. Such other components, such as formulations using purely conventional surfactants, will be used in amounts based on the desired effect.

The properties of the surfactants of this invention make them suitable as dispersants for pigments which include inorganic pigments such as titanium dioxide, pigment iron oxide (Fe2? 3) and organic pigments such as phthalocyanine blue and green pigments and carbon black and similar materials. The present surfactants are particularly useful in aqueous dispersions of titanium dioxide pigments • especially for final use in paints. Accordingly, the invention includes the use of at least one compound of this invention as dispersants for pigments in dispersions, especially aqueous dispersions, particularly titanium dioxide; and the invention further includes dispersions of pigments, especially aqueous dispersions, particularly titanium dioxide, including the compounds of this invention as dispersants. The amount of surfactant used in such dispersing applications depends on the materials used and the concentration of the dispersion required, but will usually be in the range of 0.2 to 10% by weight of the pigment. In aqueous dispersions, for inorganic pigments such as titanium dioxide pigment and iron oxide, the amount used is typically in the range of 0.05 to 5%, more usually from 0.1 to 2.5% by weight of the dispersed solid and for organic pigments such as phthalocyanine pigments and carbon black, typically the amount used is in the range of 3 to 10% by weight of the dispersed solid. Typical dispersions made using the surfactants of the invention as dispersants can contain up to about 70%, often up to about 65% of the inorganic pigment and up to about 35% by weight of the organic pigment, but this can be up to 50% by pigment pastes. When incorporated into the end-use products, such as typical pigment levels of the paints in the final product, it will be from about 3 to about 30%, particularly from about 20 to about 25%, for inorganic pigments, from about 1 to about 15% for organic pigments, particularly from about 10 to about 12%, especially for phthalocyanine-type organic pigments and from about 0.5 to about 5%, particularly from about 3 to about 3% for carbon black. The continuous phase in such dispersions will usually be water, but the surfactants of this invention can also be used in dispersion solids, particularly pigments such as those described above, in non-aqueous media such as white spirit or aromatic media. The invention further includes a paint including a pigment dispersion as described above.

Surfactants also find use in household detergents and the invention therefore includes the use of the compounds of this invention as surfactants in household detergents, particularly in heavy duty laundry powders and liquids, particularly in heavy duty laundry liquids substantially not watery; and the invention further includes household detergents, particularly in heavy duty laundry powders and liquids, particularly substantially non-aqueous heavy duty laundry liquids, including at least one compound of this invention as a surfactant. In laundry applications the surfactants of this invention can be used as only surfactants or in combination with one or more other nonionic, anionic and / or cationic surfactants. The formulations include surfactants of this invention for laundry use, typically also including other components including one or more of builders or additives; corrosion inhibitors such as sodium silicate or disilicate; anti-redeposition aids such as carboxymethylcellulose; and optical brighteners. Other commonly used components include perfumes; enzymes including lipases, proteases, cellulases and / or amylases; bleaches, typically based on sodium perborate, sodium percarbonate or similar materials, which will typically be used with bleach activators such as tetraacetylethylenediamine (TAED); and stabilizers such as phosphonates or ethylenediamine tetraacetic acid (EDTA) usually as the sodium salt; soaps; agents for foam control (soaps are frequently used for this purpose) and fabric conditioners (softeners) such as quaternary ammonium salts and amine oxides, which may be coated in bentonite-type clays. The improvers typically used in laundry formulations include phosphate-based improvers, particularly sodium tripolyphosphate; organic improvers such as citrate and / or tartrate; and / or zeolite improvers. The powder formulations will often include flow and / or filter aids and may include comixes such as sodium carbonate and / or bicarbonate, particularly in powders, where the improver is a zeolite. However, because the materials typically used as co-builders are alkaline, these will usually not be used in formulations intended for hand washing. The detergent systems for laundry, liquids are of two broad types, non-aqueous liquids and aqueous liquids. Non-aqueous liquids include a non-aqueous diluent or carrier such as liquid polyethylene glycol (PEG) such as PEG 150 to 400. The surfactant materials are dispersed in the diluent or carrier usually as miscible liquid phase materials and solid materials, in a usual manner mainly improver; co-mej speaker when used; bleach when used; and anti-corrosion aids are typically dispersed as finely divided solid materials in the diluent or carrier. As described in the above specifications numbers EP 0120569 B and EP 0030096 B such laundry liquids can be made as stable suspensions. Liquid, aqueous laundry liquids can be subdivided into two types: liquids with additive, where a solid improver is suspended in a detergent, which uses significant amounts of water as the diluent or carrier; and liquids without improver in which the volume of the product is liquid detergent material. Such aqueous systems, especially aqueous systems with additive, can not easily have their cleaning power increased by the inclusion of simple solid whitening agents since they tend to be unstable in the presence of water and the protection of the decomposition bleaches in Presence of free water is in the present complex and relatively expensive. Co-builders such as sodium carbonate and / or dicarbonate are sometimes also used with improvers in an aqueous formed system and a non-aqueous formed system. There is a recent trend to include relatively small amounts of breeders, usually organic improvers such as citrate or tartrate in aqueous "non-additive" formulations. Although such liquids may include alkaline co-builders, they are not usually used. The typical composition ranges for heavy-duty laundry products of these types are set out in the following table: (Preferred ranges in parentheses) 1 total surfactant includes the surfactant of this invention within the nonionic part and soap included in powders and aqueous formed systems mainly as antifoam. 2 the total improver includes co-mej orators, anti-corrosion aids and anti-redeposition auxiliaries, 3 water excluding the water of crystallization, 4 the bleach is optional on all types of formulations - the total bleach includes bleach, bleach activator and bleach stabilizer. The following Examples illustrate the invention, including the manufacture and properties of the compounds of the invention and their end uses, particularly illustrating the versatility and utility of the compounds of the invention. All parts and percentages are by weight unless otherwise specified.

Materials MPG mono-propylene glycol glyphosate N-phosphonomethylglycine as the isopropylamine sulfosate N-phosphonomethylglycine salt as the trimethylsulfonium salt ETA adjuvant formulation of ethoxylated ceboamine conventionally used with glyphosate AL 2042 commercially available alkylpolysaccharide adjuvant, conventionally used with the sulfosate available from ICI Methods of Proof of Property of the Compound For the products made pure (Examples of Synthesis SEI to SE6 and SEll) the materials tested were pure materials obtained from the synthesis; for products made using solvents / diluents, (Synthesis Examples SE7 to SE9) the materials tested were the materials obtained from the synthesis, which included approximately 30% reaction solvent / diluent.

Surface Tension (ST) was measured in an aqueous solution at 0.1% w / w by the drop method at 23 ° C; the results are in mN.m "" 1 (m mN.m-1 = 1 dyne.cm-1). Turbidity Temperature (CP) was measured by ASTM D 2024-65; the results are in ° C). Wetting (Wtg) Draves wetting was evaluated using the skein test (ASTM D 2281-68); the results are in seconds [or minutes] - for slow humidifiers]. Foam height (FH) Ross Miles foam height was evaluated by ASTM D 1173-53 at 25 ° C; the results are in mm.

Synthesis of Examples SE to SE13 SEl - Bis (N-methylglucamide) of dodecenylsuccinic acid Dimethylester of dodecenylsuccinic acid methanol (50 g, 1.56 moles) is added to the dodecenylsuccinic anhydride (200 g, 0.75 moles) and the reaction mixture is then heated to reflux and stirred for 1 hour. hour at a temperature of the reaction mixture of about 100 ° C with methanol brought to reflux. A catalytic amount of sulfuric acid (98% w / v, 0.5 ml) is then added, methanol / water mixture removed by distillation and fresh methanol is added to maintain the volume of the reaction mixture. After about 2 hours, approximately 500 ml of methanol was added and the completion of the reaction was confirmed by the absence of any significant anhydride or acid peak in the IR spectrum of a sample of the reaction mixture. The excess methanol is distilled off, the reaction mixture is allowed to cool to room temperature, neutralized with sodium hydrogen carbonate and residual solids are removed by filtration. The liquid dimethyl ester product is obtained in a substantially quantitative yield. The H1 NMR spectrum of the ester product (without further purification) showed 6 methyl ester protons per molecule and the C13 NMR spectrum showed the absence of anhydride or acid functionality. bis (N-methylglucamide) of dodecenylsuccinic acid N-methylglucamine (119 g, 0.6 moles) is added to a dimethylester of pure dodecenylsuccinic acid (100 g, 0.3 moles), the mixture is then heated to 120 ° C and stirred under vacuum that temperature for 4 hours, time after which the IR spectrum of a sample of the reaction mixture, showed that none of the ester groups remained (ester band of 1740 cm-1) and that the significant amide product had formed (Amide band of 1618 cm "1) Following the reaction by the IR spectrometer showed a stable decrease of the ester band as the amide band was reinforced, similarly, following the reaction by both of C13 and RMN H1 showed a reduction in the intensity of the peaks of ester CH3 and amine NCH3 as the peak of amide NCH3 appeared and increased during the reaction.The reaction mixture is allowed to cool to room temperature to give the product bis-glucamide as a glassy solid in a quantitative yield The identity of the product was confirmed by C13 and H1-NMR The properties of the compound SEl are as follows: Property Value Units Surface Tension 39.9 mN.m-1 Turbidity Temperature> 98 ° C Humidity Draves 68 seconds Ross Foam Heights Miles 0 min. 5 min (@ 60 ° C) 99 81 mm SE2 - SE6 Octenyl to bis (N-methylglucamide) of octadecenylsuccinic acid The title compounds are made by the method described in the Synthesis of Example SEI, but substituting the corresponding alkenyl succinic anhydride for the dodecenylsuccinic anhydride used in SEl. The products were all vitreous solids obtained in a quantitative yield. The identity of the products was confirmed by C13 and H1 NMR. The products of these Examples are: SE2 - bis (N-methylglucamide) of octenylsuccinic acid SE3 - bis (N-methylglucamide) of decenylsuccinic acid SE4 - bis (N-methylglucamide) of tetradecenylsuccinic acid SE5 - bis (N-methylglucamide) of hexadecenylsuccinic acid SE6 - octadecenylsuccinic acid bis (N-methylglucamide) SE7 - bis (N-methylglucamide) of dodecenylsuccinic acid N-methylglucamide (62.5 g, 0.32 moles) is added to a freshly prepared solution of dodecenyl dimethyl ester (50 g, 0.16 moles) I made as described in SEl) in polyethylene glycol 200 (PEG 200) (50 g). The reaction mixture is heated to 80 ° C under vacuum, maintained at this temperature for 1 hour, then the temperature is increased to 100 ° C and the reaction mixture is maintained at this temperature until no other methanol is involved (approximately 8 hours) . The product is obtained as a waxy solid in a quantitative yield (including the PEG reaction of the solvent / diluent). H1 and C13 NMR NMR confirmed the identity of the product as the title compound.

SE8-SEll Decenyl to bis (N-methylqlucamide) of octadecenylsuccinic acid The title compounds were made as described in the Synthesis of Example SE7, but substituting the corresponding dimethyl ester of the corresponding alkenyl succinic acid (done as described in SE2) for the dimethyl ester of the Dodecenylsuccinic acid used in SE7. The products are obtained as waxy solids in a quantitative yield (including the PEG reaction of solvent / diluent) and the identity of the products were confirmed by C13 and H1NMR.

The products of these Examples were: SE8 - bis (N-methylglucamide) of decenylsuccinic acid SE9 - bis (N-methylglucamide) of tetradecenylsuccinic acid SE10 - bis (N-methylglucamide) of hexadecenylsuccinic acid SEll-bis (N-methylglucamide) of octadecenylsuccinic acid SE12 - bis (N-methylqlucamide) of dodecenylsuccinic acid The title compound is made by the method described in the Synthesis of Example SE7, except that monopropylene glycol (MPG) (50 g) is used as the solvent / diluent and the temperature of the reaction mixture rises directly to 100 ° C and is maintained until the evolution of the methanol is suspended (approximately 8 hours). The product is obtained as a waxy solid in a quantitative yield (including the MPG reaction of the solvent / diluent). The identity of the product was confirmed by C13 and H1 NMR.

SE13 - PEG-200-N-methyl-phenyl ester of octadecenylsuccinic acid Mono-PEG 200 octadecenylsuccinic acid ester PEG 200 (218.7 g, 1.09 mol) is added in a single portion to stir octadecenylsuccinic anhydride (382.8 g); 1.09 moles). The reaction mixture is heated at 100 ° C for 2 hours after which the infrared spectrum of a sample of the reaction mixture showed no anhydride signal (elongated frequency 1790 cm-1). A catalytic amount of sulfuric acid and methanol (50 ml) are added to the reaction mixture, the mixture is heated to 110 ° C and the methanol / water mixture is distilled off from the reaction. The fresh methanol is added at a rate to maintain the constant volume of the reaction mixture. The end point of the reaction is determined from the infrared and NMR spectrum of the samples. After completion of the esterification reaction, the excess methanol is removed by distillation, the reaction mixture is cooled, neutralized and the solids are removed by filtration as described in SEl. The diester intermediate - it is obtained as a liquid in a substantially quantitative yield and is used without further purification.

N-Methylqlucamide from PEG 200 octadecenylsuccinic acid ester N-methylglucamide (67 g, 0.344 mols) is added in an individual aliquot for the PEG 200 octadecenylsuccinic acid methyl ester (200 g, 0.334 mol) and the reaction mixture is heated to 100 ° C under vacuum until no methanol is involved (approximately 4 hours), when the H1 NMR spectrum of a sample showed the absence of methyl ester. The product of the title compound is obtained as a waxy solid in a substantially quantitative yield. The identity of the product was confirmed by C13 and H1 NMR.

SE14-SE18 Various N-methyl-glucanic acid PEG esters of alkenylsuccinic compounds The title compounds are made as described in the Synthesis of Example SE13, but substituting the corresponding alkenyl succinic anhydride for octadecenylsuccinic anhydride and the corresponding PEG for the PEG 200 used in SE13. . The products are obtained as waxy solids in a quantitative yield and the identity of the products was confirmed by C13 and H1 NMR. The products of these Examples were: SE14 - N-methylglucamide of PEG 600 ester of dodecenylsuccinic acid SE15 - N-methylglucamide of PEG 2000 ester of dodecenylsuccinic acid SE16 - N-methylglucamide of PEG 600 ester of tetradecenylsuccinic acid SE17 - N-methylglucamide of PEG 1000 ester of octadecenylsuccinic acid SE18 - N-methylglucamide methoxy of PEG 180 ester of tetradecylsuccinic acid SE19-Bis fN-methylglucamine of tetracenylsuccinic acid of PEG 800 ester The title compound is made by the general method of Example SE13, but using a molar ratio of 2: 1 ASA: PEG to form the intermediate bis [tetradecenylsuccinic acid] of PEG 800 ester; approximately twice the amount of methanol (on a molar basis) to form the intermediate bis [tetradecenylsuccinic acid methyl ester] of PEG 800 ester; and a molar ratio of 2: 1 of N-methylglucamine: bis [tetradecenylsuccinic acid methyl ester] of PEG 800 ester. The product is obtained as a waxy solid in a substantively quantitative yield. The identity of the product was confirmed by C13 and H1 NMR.

SE20 - Bis- (N-diqlucamide) of hexadecenylsuccinic acid The title compound is made by the general method of Example SE12 but substituting diglucamine with glucamine and hexadecenyl dimethyl ester for the dimethylester of the dodecenyl acid used in Example SE12. The product is obtained as a waxy solid in a substantively quantitative yield. The identity of the product was confirmed by C13 and H1 NMR.

SE21- N-methyl-3-methylalucamide N-di (2-ethylhexyl) amide of dodecenylsuccinic acid N-ethylhexylamide of dodecenylsuccinic acid Di (2-ethylhexyl) amine (48.2 g, 0.2 moles) is added to dodecenylsuccinic anhydride (53.2 g, 0.2 moles) during 2 to 3 minutes, the reaction mixture is heated to about 85 ° C and stirred at that temperature for about 2 hours before stopping stirring overnight at room temperature. The IR spectrum of a sample of the reaction mixture showed anhydride present and had strong amide and carboxylic acid peaks. The reaction mixture is used without further purification.

Methiester of the N- (2-ethylhexyl) amide of dodecenylsuccinic acid The title compound is prepared as described in Example SE13 to prepare the methyl ester of the ester PEG 200 ester of octadecenylsuccinic acid, but using the N- (2-ethylhexyl) amide of the dodecenylsuccinic acid from the previous step in place of the PEG 200 ester of octadecenylsuccinic acid used in SE13. The title compound was obtained as a liquid in a substantively quantitative yield. The structure of the compound was confirmed by the spectrum H1 and C1-NMR.

N-ethylhexylamide of the N-methyl-glucocide of dodecenylsuccinic acid The title compound is prepared as described in Example SE13 to prepare the ester of the N-methylglucamide PEG 200 of octadecenylsuccinic acid of the methyl ester precursor, but using methyl ester of the N- (2-ethylhexyl) amide of dodecenylsuccinic acid from the previous step, instead of the methyl ester of the PEG 200 ester of octadecenylsuccinic acid used in SE13. The title compound was obtained as a waxy solid in a substantively quantitative yield. The structure of the compound was confirmed by the H1 and C13 NMR spectrum. The properties of the products made in the Synthesis Examples are summarized in Table 1 below.

Table 1 Applications of Examples AE1 to AE3 of Formulation Applications Aqrosuimics Application test methods The herb control was evaluated by generating European Weed Research Council (EWRC) classifications: where 1 = no control and 9 = 100% control, at 3, 7, 14 and 28 days after treatment. Inhibition of the Diameter (DI%) the test was carried out by infecting a petri dish containing a suitable growth medium with the target fungus, once the fungus covers the surface of the medium, a small filter paper disc impregnated with the formulation Test is placed on the surface of the disc, the area of the surface of the medium that becomes free of the fungus is measured and the equivalent diameter is the ID. All the values of the DI used in the subsequent calculations are the average values of four reapplications. The greater the better results. The results are cited as the numerical percentage of the DI for a test formulation based on the DI for the antifungal material applied as its normal application index (NAR) without an adjuvant - the higher the percentage the more effective the adjuvant is). The test formulations were applied at half the normal application rate. Diameter of growth the fungus (FGD%) the test was carried out preparing a growth medium that includes a fungicidal formulation and placing a disc infected with the target fungus on the medium in a petri dish. The effectiveness of the formulation is measured by the area that becomes infected with the fungus. The greater the area infected, the less effective the formulation is. Again, all results are based on four reapplications of all runs. The infected area is expressed as an equivalent diameter and the results are cited as the efficiency ratio (%) which is = 100 x (the diameter when the fungicide was not used - the diameter when the formulation contains fungicides) / (the diameter when it is not used fungicide).

Example AE1 - Herbicidal formulations containing glyphosate Herbicidal formulations from Fl to F8 based on the glyphosate isopropylamine salt are prepared by dissolving the glyphosate salt at 360 gl "1 and the adjuvant (in some cases including a solvent or a cosolvent) at 180 gl- 1 in water A control formulation CF1 is prepared using ETA as the adjuvant (to give a typical current formulation for the herbicide glyphosate.) The formulations were used in a test spray program, in which the formulation was sprayed onto the containers Test at a rate or rate of 4 l.ha-1 of the formulation in a spray volume of 250 l.ha "1 using 4 replications. The results of the formulations used in the control of the obtained grass are summarized in Table 2 below.

Table 2 Example AE2 - Herbicidal Formulations Containing Sulfosate The herbicidal formulations F9 to F16 based on glyphosate such as the trimethylsulfonium salt are prepared by dissolving the sulfosate at 360 gl "1 and the adjuvant (in some cases including a solvent or a cosolvent) at 180 gl-1. in water A CF2 control formulation was prepared using AL 2042 as the adjuvant (to give a typical current formulation for the sulfosate herbicide.) The formulations were used in a test spray program, in which the formulation was sprayed onto the containers Test at a rate or rate of 3 l.ha-1 of the formulation in a spray volume of 250 l.ha "1 using 4 replications. The ormulations used and the results of the control of obtained herbs are summarized in Table 3 below.

Table 3 Example AE3 - Antifungal Formulations Various antifungal formulations were prepared and tested in vi tro by the methods described in the foregoing.

The antifungal materials used were commercially available, conventional materials. The effectiveness of the surfactants of this invention as adjuvants was evaluated by preparing appropriate formulations, testing them and comparing them with the formulations that do not use the adjuvants. The formulations without results are summarized in Table 4 below, in which the adjuvants are identified by the numbers of the Synthesis Example (SE).

Table 4 Examples of Applications of Pigment Dispersion AE4 Dispersions of pigment grade iC > 2 in water are made based on the following formulation: Material Weight (g) Pigment of Ti02 65 Surfactant 1 n-hexanol - antifoam 0.5 water for 100 The surfactant was weighed in a 250 ml glass bottle, the calculated amount of demineralized water is added followed by n-hexanol and the mixture is usually mixed to bring the surfactant into a solution. Glass beads of 3 ml (approximately 50 g) are added followed by the pigment. The dispersion was stirred using a Red Devil laboratory shaker for 1/2 hour. The viscosity of the dispersion was measured using a Brookfield LVT viscometer at 6 rpm (0.1 Hz). The viscosity of the dispersion and the surfactants used are reported in Table 5 below.

Table 5 Examples of AE5 Applications of Laundry Liquids - Household Detergents Test formulations of a non-aqueous, heavy-duty laundry liquid are made as follows: Material parts by weight sodium disilicate 2.0 optical brightener 0.3 EDTA 0.2 carboxymethylcellulose 1.0 pigment iC > 2 0.2 Sodium Carbonate 4.9 Sodium Tri-Polyphosphate 40.9 PEG 200 39.4 Product of SIR 10.0 The formulations were tested by the use of a Tergotometer washing machine (manufactured by United States Testing Company) with water of standard hardness of 50 or 300 ppm at 40 or 60 ° C and using 3 gl-1 or 6 gl "1 of the formulation (a total of eight runs) Each wash used for standard test viz fabrics: EMPA cotton 101, EMPA polycotton 104, cotton Krefeld 10C, Krefeld 20C polycotton The reflectance of the fabrics was measured before and after washing and the percentage increase in reflectance was reported as the result of the test.The results are set forth in Table 6 below.

Table 6 Corridaí Hidrogena- 1 Temp. , conc "! Increase in Reflectance during washing (%) No. j0 '*"! (* C)! < g-i "1) i EMPA 101 EMPA 104 IKrefßld 10CIKrefeld 20C 1 l 300 40 3! 24.5 45 '2T.9! 40.8 2; 50, 40 3, 34 47.8, 36.7, 47.6 3 i 300 40 ß! 32.2 46.8 s 35.7 50.1 4 ¡50 40: 6 '34.8 48 1 37 51.2! 1 300 60 i 3 43.7 49.4 | 44.4 47.9 6 1 50 60 3 46.8 48.6! 46.1 51 7 | 300 60 I 6 48.7 i 49.2 47 1 '51.9 ß 1 50 60 6 48.6 49.1! 46.7 i 52.7

Claims (22)

1. A compound of the formula (I) (R ^ .C.CO.R5 characterized in that one of R1 and R ^ in the succinic acid portion is Cg to C22 alkyl alkenyl and the other is hydrogen; R3 is a hydrocarbyl polyhydroxy radical; R4 is hydrogen, C- ^ to C22 hydrocarbyl, or R4 is independently as defined above for R3; R5 is a group: -NR3R4, wherein R3 and R4 are independently as defined above; or R5 is a group: -0. (A0) n.R6, where: AO is an alkylene oxide residue; n is from 1 to 200; and R6 is hydrogen, C- ^ to C22 hydrocarbyl; or R6 is a group: I (R ^ .C.CO. wherein R1, R2, R3 and R4 are independently as defined above; or R5 is a group: -NR7R8, where: R7 is hydrogen, hydrocarbyl of C- ^ to C22; and R8 is hydrocarbyl of C ^ to C22; or -NR7R8 is a pyrrolidino, piperidino, morpholino, piperazino or a N- (C- to Cg alkyl) piperazino group; or -NR7R8 is a group of the formula -NH. (A0) n.R9, where AO and n are as defined above and R9 is a hydrocarbyl group of C- ^ to C22; or -NR7R8 is a group of the formula -NH. (AO) p.CH2CH2.OR10, where AO is as defined in the above; p is from 0 to 200, particularly from 0 to 100; and R 0 is a C- | _ to C22 hydrocarbyl; or R! ° is a group: (R'HJ.C.CO.NR ^ 4 I { R ^ .C.CO. where R1, R2, R3 and R4 are independently as defined in the foregoing.

2. The compound according to claim, characterized in that it has the formula (la): where R1, R2, R3 and r4 are independently as defined in claim 1.

3. The compound according to claim 1, characterized in that it has the formula (Ib): n.R where R1, R2, R3, R4, AO, n and R6 are as defined in claim 1.

4. The compound according to claim, characterized in that it has the formula (le): (le) (R1H) .C.CO.NR3R4 I (R2H) .C.CO.O. (AO) p.CO.C. (HR2) 1 (R'H) .C.CO.NR3R4 where R1, R2, NR3R4, AO and n are as defined in claim 1.

5. The compound according to claim, characterized in that it has the formula (Id): (^ CCO H ÍAOJ ^ where R1, R2, R3, R4, AO, n and R9 are as defined in claim 1.

6. The compound according to claim, characterized in that it has the formula (le): (le) (R1H) .C.CO.NR3R4 where R1, R2, R3, R4, AO and p are as defined in claim 1.

7. The compound according to claim, characterized in that it has the formula (If): where R1, R2, R3, R4, R7 and R > ^ 8 are as defined in claim 1

8. The compound according to any of claims 1 to 7, characterized in that one of R1 and R2 in the succinic acid portion is a straight chain C8 to C18 alkenyl group and the other is hydrogen.

9. The compound according to any of claims 1 e? 8, characterized in that R3 is of the formula -CH2. (CHOH) 4. CH20H and R4 is hydrogen or a methyl, ethyl, propyl or butyl group.

10. The compound according to any one of claims 1 to 9, characterized in that R 4 is an alkyl group of C 1 to C 20, an aralkyl group of C 7 to C 12 ° an alkyl group substituted with hydroxyl of C 2 to C 20; AO is a residue of ethylene oxide; n and p are each independently from 3 to 50; R6, R7, R8 and R10 are each independently an alkyl group from C ^ to Cg; and R9 is an alkyl group of C ^ to C2.

11. The compound according to any of claims 1 to 10, characterized in that these are plural groups R1 / R2 and / or -NR3R4 and the respective groups R1 / R2 and -NR3R4 are the same.

12. A method of making a compound according to any of claims 1 to 11, characterized in that it comprises reacting an ester of a corresponding substituted succinic acid with an alcohol of the formula R1: I-OH, wherein R11 is an alkyl group of C - ^ to C4 with an amine of the formula H.NR3R4, where R3 and R4 are as defined in claim 1, in a molar ratio corresponding to the number of functions of -NR3R4 amide in the final product and eliminating the alcohol R110H generated by distillation.

13. An agrochemical formulation characterized in that it includes at least one agrochemical active component and a compound according to any of claims 1 to 11 as a surfactant and / or adjuvant.

14. An agrochemical formulation according to claim 13, characterized in that it includes one or more herbicides such as glyphosate and sulfosate, fungicides such as iprodione, carbendazim and propionazole, insecticides, acaricides and / or plant growth regulators as a component or agrochemically active components. .

15. An agrochemical formulation according to any claim 13 or claim 14, further characterized in that it includes one or more oils; solvents and / or diluents; and other anionic, cationic or non-ionic surfactants.

16. A dispersion of a pigment in a liquid carrier characterized in that it includes as a dispersant a compound of the formula (I), according to any of claims 1 to 12.

17. A dispersion according to claim 16, characterized in that the pigment is titanium dioxide and the liquid carrier is water.

18. A dispersion according to any claim 16 or claim 17, characterized in that the compound of the formula (I) is used in an amount of 0.2 to 10% by weight of the pigment.

19. A paint characterized in that it includes a dispersion of a pigment according to any of claims 16 to 18.

20. A domestic detergent characterized in that it includes at least one of the compounds according to any of claims 1 to 12 as surfactants.

21. A household detergent in the form of a non-aqueous heavy-duty laundry liquid, characterized in that it includes at least one of the compounds according to any of claims 1 to 12 as surfactants.

22. A household detergent according to any claim 20 or 21, further characterized in that it includes one or more other nonionic, anionic and / or cationic surfactants; breeders; corrosion inhibitors; anti-redeposition aids such as carboxymethylcellulose; optical brighteners, perfumes; one or more enzymes lipase, protease, cellulose and / or amylase; optionally bleaching with one or more bleach activators and / or stabilizers; soaps; agents for foam control; and fabric conditioners.