Classifications

• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
  • C11D3/16—Organic compounds
  • C11D3/37—Polymers
  • C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • C11D3/3769—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
  • C11D3/3773—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines in liquid compositions

Definitions

• EP-PS 0 116 930 describes water-soluble copolymers of 40 to 90% by weight of at least one ethylenically unsaturated monocarboxylic acid with 3 to 5 C atoms and 60 to 10% by weight of at least one ethylenically unsaturated dicarboxylic acid with 4 to 8 C atoms and / or their corresponding dicarboxylic acid anhydrides are known, in which 2 to 60% by weight, based on the total weight of the carboxylic acids or carboxylic acid anhydrides, are esterified with alkoxylated C1 to C18 alcohols or C1- to C12 alkylphenols.
• the partially esterified copolymers and their water-soluble salts are used, inter alia, in amounts of 0.5 to 10% by weight also used in liquid detergent formulations.
• the compatibility of the partially esterified copolymers of at least one monoethylenically unsaturated monocarboxylic acid and at least one monoethylenically unsaturated dicarboxylic acid is significantly more favorable than that of the non-esterified products, so that there are fewer phase separations.
• the partially esterified copolymers of the type described are not stable to hydrolysis, so that they hydrolyze in liquid detergent formulations. As a result, inhomogeneities occur, which can even go so far as to result in phase separation of the liquid detergent.
• liquid detergents which contain at least one nonionic surface-active agent in an amount of 5 to 25% by weight, 2 to 25% by weight of a builder, approximately 1 to 10% by weight of C4- to C30 Contain ⁇ -olefin-maleic anhydride copolymers and, to make up to 100% by weight, water. Although these liquid detergents initially represent clear solutions, they separate relatively quickly during storage.
• liquid alkaline detergent formulations which, in addition to water and detergents as stabilizers, contain 0.1 to 5%, based on the entire formulation, of a hydrolyzed copolymer of an ⁇ , ⁇ -unsaturated carboxylic anhydride with a vinyl ester, vinyl ether or contain an ⁇ -olefin in partially esterified form.
• Addition products of alkylene oxides, in particular ethylene oxide onto alkylphenols are also suitable as alcohol components for the esterification. Only 0.01 to 5% of the carboxyl groups of the copolymer are present as ester groups.
• these liquid detergents contain components which are compatible with one another, the primary washing action of this liquid detergent formulation is still in need of improvement.
• EP-A-0 215 251 describes the use of homopolymers of acrylic acid and methacrylic acid, copolymers of acrylic acid and methacrylic acid and of copolymers of ethylenically unsaturated dicarboxylic acids with 4 to 6 carbon atoms and acrylic acid or methacrylic acid in each case partially neutralized and / or with long-chain amines and / or partially amidated form known as graying-inhibiting additive to detergents and cleaning agents which promotes the primary washing action in amounts of 0.05 to 10% by weight.
• the partially amidated homopolymers and copolymers are prepared by reacting the polymers with long-chain amines. In many cases they still contain free amines, which are undesirable in detergent formulations because of their smell and physiological concern.
• the polymers partially neutralized or partially amidated with long-chain amines are used to produce powder detergents. The reference does not indicate that the products described therein could be suitable for the production of stable liquid detergents.
• the present invention has for its object to provide polymers for the preparation of stable liquid detergent formulations which have an improved primary and secondary washing action compared to the liquid detergent formulations of the prior art.
• stable liquid detergent formulation should be understood to mean the fact that the individual components of the formulation are compatible with one another and do not separate even after prolonged storage.
• liquid detergents which contain the copolymers to be used according to the invention, when mixed with aqueous neutral to alkaline solutions of anionic and / or nonionic surfactants, give clear aqueous solutions which are stable on storage, i.e. the individual components of the liquid detergent formulation are compatible with one another and do not separate after prolonged storage.
• the copolymers to be used according to the invention contain, as essential components, units of monoethylenically unsaturated C3 to C8 monocarboxylic acids, monoethylenically unsaturated C4 to C8 dicarboxylic acids, half esters of monoethylenically unsaturated C4 to C8 dicarboxylic acids, esters of monoethylenically unsaturated C3 to C2 carboxylic acids, - Polymerized to C30-olefins, styrene, C1- to C3-alkylstyrenes, C1- to C28-alkyl vinyl ethers, vinyl esters of saturated C1 to C8-carboxylic acids or mixtures of units of these monomers.
• the ethylenically unsaturated C3 to C8 monocarboxylic acids include, for example, acrylic acid, methacrylic acid, vinyl acetic acid, allylacetic acid, propylidene acetic acid, ethylidene acetic acid, ⁇ -ethyl acrylic acid and ß, ß-dimethylacrylic acid. From this group of monomers, acrylic acid and methacrylic acid are preferably used.
• Suitable monoethylenically unsaturated C4 to C8 dicarboxylic acids are, for example, maleic acid, itaconic acid, fumaric acid, mesaconic acid, methylene malonic acid and citraconic acid.
• copolymers to be used according to the invention preferably contain units of maleic acid or itaconic acid copolymerized.
• Half-esters of monoethylenically unsaturated C4 to C8 dicarboxylic acids which are derived from mono- or polyhydric alcohols having 1 to 8 C atoms are also suitable.
• Such alcohols are, for example, methanol, ethanol, n-propanol, isopro panol, n-butanol, sec-butanol, 2-ethylhexyl alcohol, glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 1,2-butanediol and 1,6-hexanediol.
• the alcohols mentioned can also be used for the preparation of esters of monoethylenically unsaturated C3- to C8-monocarboxylic acids, which are also suitable as component (a) for the preparation of the copolymers to be used according to the invention.
• esters are, for example, methyl acrylate, ethyl acrylate, butyl acrylate, 2-ethylhexyl acrylate, hydroxyethyl acrylate, hydroxypropyl acrylate and the corresponding esters of methacrylic acid.
• Suitable olefins having 2 to 30 carbon atoms are, for example, ethylene, propylene, isobutylene, n-hexene, n-octene, diisobutene, n-decene, n-dodecene and n-octadecene.
• the longer-chain olefins can have the double bonds in the ⁇ or also in the ⁇ position.
• the use of ⁇ -olefins is particularly preferred.
• Preferably used as olefins are branched C6 to C18 olefins or mixtures thereof.
• mixtures of 2,4,4'-trimethylpentene-1 and 2,4,4'-trimethylpentene-2 is particularly preferred.
• Commercially available mixtures of diisobutylene contain approximately 80% trimethylpentene-1 and approximately 20 trimethylpentene-2.
• the copolymers may also contain units of styrene or C1- to C3-alkylstyrenes polymerized as an essential component of component (a).
• Suitable alkylstyrenes are, for example, ⁇ -methylstyrene and ⁇ -ethylstyrene.
• Component (a) are also C1 to C28 alkyl vinyl ethers, such as methyl vinyl ether, ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, isobutyl vinyl ether, n-hexyl vinyl ether, n-octyl vinyl ether, dodecyl vinyl ether and octadecyl vinyl ether.
• vinyl esters of saturated C1 to C8 carboxylic acids for example vinyl formate, vinyl acetate, vinyl propionate and vinyl butyrate.
• the copolymers contain mixtures of units of monoethylenically unsaturated C4- to C8-dicarboxylic acids with units of half-esters of monoethylenically unsaturated C4- to C8-dicarboxylic acids, esters of monoethylenically unsaturated C3- to C8-monocarboxylic acids, C2- bis C30-olefins, styrene, C1- to C3-alkylstyrenes, C1- to C28-alkyl vinyl ethers, vinyl esters of saturated C1- to C8-monocarboxylic acids, monoethylenically unsaturated C3- to C8-monocarboxylic acids or optionally their salts in copolymerized form.
• Preferred monoethylenically unsaturated C4 to C8 dicarboxylic acids are maleic acid and itaconic acid.
• the units of these dicarboxylic acids are in the preferred embodiment of the invention except for the others Dicarboxylic acid units, with the units of at least one other monomer, which are mentioned under (a), contained in the copolymers.
• the monomers of component (a) make up 50 to 99, preferably 60 to 90 mol% of the copolymers.
• the amides of component (b) are preferably derived from the amides of acrylic acid and methacrylic acid and the mono- and diamides of maleic acid and itaconic acid of the amide structures given above.
• the Amides of the Com Component (b) of the copolymers are prepared, for example, by using a monoethylenically unsaturated C3 to C8 carboxylic acid or the acid chlorides of these carboxylic acids with amines of the formula in which the substituents R1 and R2 have the meaning given above for the amide structure, to the amides or half-amides or diamides in a known manner.
• R-OH C1- to C28-alkyl
• the following compounds are suitable as amides of ethylenically unsaturated compounds of component (b):
• the monomers of component (b) make up 50 to 1, preferably 40 to 10 mol%, of the copolymers.
• the copolymers can be obtained by copolymerizing the monomers specified under (a) and (b) by the customary methods of substance, solution, precipitation or suspension polymerization using initiators which decompose into free radicals under the polymerization conditions.
• the polymerization temperatures are in the range from 30 to 200 ° C. A shorter polymerization time is required at a higher temperature, while a longer polymerization time has to be accepted at lower temperatures.
• Suitable inert organic solvents are e.g. Toluene, o-xylene, p-xylene, m-xylene, isopropylbenzene, tetralin, tetrahydrofuran, dioxane and aliphatic hydrocarbons, such as hexane, cyclohexane, n-heptane, n-octane, isooctane and mixtures of the solvents mentioned.
• the esterification is preferably carried out only to such an extent that about 5 to 50% of the carboxyl groups formed from the anhydride groups during the hydrolysis are esterified.
• Copolymers of this type which are partially esterified, for example, with an adduct of 10 moles of ethylene oxide and 1 mole of a C13- / C15-oxo alcohol, have particular stability in alkaline aqueous liquid detergent formulations.
• the residues R1 and R2 of the amide structures of the compounds of formula (b) are derived - as already mentioned - preferably from alkoxylated C1 to C28 alcohols.
• the alkoxylation of these alcohols can be carried out using ethylene oxide alone, with mixtures of ethylene oxide and propylene oxide and, if appropriate, butylene oxides, or else as block copolymerization, by first adding propylene oxide and then ethylene oxide or in the reverse order, ie first ethylene oxide and then propylene oxide, to the alcohols.
• the end group in the two block copolymers described can be a butylene oxide grouping.
• the amides to be used according to (b) generally contain enough ethylene oxide units to ensure that these monomers are soluble in water.
• copolymers which contain at least one monomer from groups (a) and (b) in copolymerized form as essential units, can optionally contain in copolymerized form further ethylenically unsaturated monomers which are different from (a) and (b) and dissolve in water.
• Such monomers are, for example, acrylamide, methacrylamide, acrylonitrile, methacrylonitrile, vinylsulfonic acid, allylsulfonic acid, methallylsulfonic acid, 2-acrylamidomethylpropanesulfonic acid, N-vinylpyrrolidone, N-vinylcaprolactam, N-vinylformamide, vinylphosphonic acid, N-vinylimidazole, N-vinylethanolimylamylamethylamylamylamylamylamethylamylamethylamylamylamethylamylamethylamylamethylamylamethylamylamethylamylamethylamylamethylamylamethylamylamethylamylamethylamylamethylamylamethylamylamethylamylamethylamylamethylamylamethylamylamethylamylamethylamylamethylamylamethylamylamethylamylamethylamylamethylamylamethylamylamethylamylamethylamylamethylamylamethyl
• the basic monomers are preferably used as salts or in quaternized form.
• the monomers containing acid groups can also be polymerized in partially or completely neutralized form. If these monomers are used in the preparation of the copolymers to be used according to the invention, they are present in the copolymerization in amounts of 1 to 20% by weight, based on the monomers (a) and (b).
• the copolymerization can optionally be carried out in the presence of conventional regulators, e.g. Thio and mercapto compounds, such as mercaptoethanol, mercaptopropanol, mercaptobutanol, mercaptoacetic acid, mercaptopropionic acid, thiolactic acid, n-butyl mercaptan, tert-butyl mercaptan, octyl mercaptan and dodecyl mercaptan.
• suitable regulators are aldehydes, such as acetaldehyde, butyraldehyde, acrolein and methacrolein, and allyl compounds, e.g.
• the regulators are used in amounts of 0.01 to 20, preferably 0.05 to 10,% by weight, based on the monomers used.
• Chain extenders contain at least 2 ethylenically unsaturated double bonds that are not conjugated.
• Suitable chain extenders of this type are, for example, diacrylates or dimethacrylates of at least dihydric saturated alcohols, for example ethylene glycol diacrylate, ethylene glycol dimethacrylate, 1,2-propylene glycol diacrytate, 1,2-propylene glycol dimethacrylate, butanediol-1,4-diacrylate, butanediol-1,4-dimethacrylate, Hexanediol diacrylate, hexanediol dimethacrylate, neopentyl glycol diacrylate, neopentyl glycol dimethacrylate, 3-methylpentanediol diacrylate and 3-methylpentanediol dimethacrylate
• Acrylic acid and methacrylic acid esters of alcohols with more than 2 hydroxyl groups can also be used as chain extenders, for example trimethylolpropane triacrylate or tri methylolpropane trimethacrylate.
• Another class of chain extenders are diacrylates and dimethacrylates of polyethylene glycols or polypropylene glycols with molecular weights which are preferably in the range from 400 to 2,000 each.
• block copolymers of ethylene and propylene oxide or statistical copolymers of ethylene and propylene oxide are also suitable, each of which is esterified in the ⁇ , ⁇ position with acrylic acid, methacrylic acid or maleic acid.
• Chain extenders of this type are, for example, diethylene glycol diacrylate, diethylene glycol dimethacrylate, triethylene glycol diacrylate, triethylene glycol dimethacrylate, tetraethylene glycol diacrylate and / or tetraethylene glycol dimethacrylate as well as the diacrylates or dimethacrylates of polyethylene glycols from C 3 or vinyl itaconate.
• vinyl esters of saturated carboxylic acids containing at least 2 carboxyl groups and di- and polyvinyl ethers of at least dihydric alcohols, for example divinyl adipate, butanediol divinyl ether and trimethylolpropane trivinyl ether.
• Further chain extenders are allyl esters of ethylenically unsaturated carboxylic acids, for example allyl acrylate and allyl methacrylate, allyl ethers of polyhydric alcohols, for example pentaerythritol triallyl ether, triallylsucrose and pentaallylsucrose.
• Methylene bisacrylamide, methylene bis methacrylamide, N-divinylethylene urea, divinylbenzene, divinyldioxane, tetrallylsilane and tetravinylsilane are also suitable as chain extenders. If the copolymerization of the monomers (a) and (b) is carried out in the presence of chain extenders, they are used in amounts of from 0.01 to 20, preferably up to 10,% by weight.
• Regulators and chain extenders can also be used together in the copolymerization to produce polymers with special properties.
• copolymers which have K values of 8 to 200, preferably 10 to 80 (determined according to H. Fikentscher in one percent aqueous solution at 25 ° C. and pH 7.5 in the form of the sodium salt).
• the K values correspond to molecular weights (weight average) of about 500 to 500,000, preferably 1,000 to 150,000.
• the composition of the copolymer should always be chosen so that the copolymers in the form of the free acid or at least as salts are soluble or dispersible in water.
• copolymers to be used according to the invention can be in the form of the free acids, in partially or completely neutralized form and in each case added to liquid detergents in one of these forms.
• the copolymers which contain units of the monomers (a) and (b) in copolymerized form are water-soluble or water-dispersible at least in the form of the salts.
• the liquid detergent formulations which contain the partially esterified copolymers described above in an amount of 0.1 to 20, preferably 1 to 10% by weight, are usually made alkaline and have at least one anionic surfactant, a nonionic surfactant or as a further essential constituent their mixtures and water. These are clear aqueous solutions.
• Suitable anionic surfactants are, for example, sodium alkylbenzenesulfonates, fatty alcohol sulfates and fatty alcohol polyglycol ether sulfates.
• Individual compounds of this type are, for example, C8 to C12 alkyl benzene sulfonates, C12 to C16 alkane sulfonates, C12 to C16 alkyl sulfates, C12 to C16 alkyl sulfosuccinates and sulfated ethoxylated C12 to C16 alkanols.
• anionic surfactants are sulfated fatty acid alkanolamines, fatty acid monoglycerides or reaction products of 1 to 4 moles of ethylene oxide with primary or secondary fatty alcohols or alkylphenols.
• anionic surfactants are fatty acid esters or fatty acid amides of hydroxy or amino carboxylic acids or sulfonic acids, such as, for example, the fatty acid sarcosides, glycolates, lactates, taurides or isothionates.
• the anionic surfactants can be in the form of the sodium, potassium and ammonium salts and also as soluble salts of organic bases, such as mono-, di- or triethanolamine or other substituted amines.
• the anionic surfactants also include the usual soaps, ie the alkali salts of the natural fatty acids.
• Nonionic surfactants e.g. Addition products of 3 to 40, preferably 4 to 20, moles of ethylene oxide and 1 mole of fatty alcohol, alkylphenol, fatty acid, fatty amine, fatty acid amide or alkanesulfonamide can be used.
• the addition products of 5 to 16 moles of ethylene oxide with coconut oil or tallow fatty alcohols, with oleyl alcohol or with synthetic alcohols with 8 to 18, preferably 12 to 18 carbon atoms, and with mono- or dialkylphenols with 6 to 14 carbon atoms in are particularly important the alkyl residues.
• non-fully or not fully water-soluble polyglycol ethers with 1 to 4 ethylene glycol ether residues in the molecule are also of interest, in particular if they are used together with water-soluble nonionic or anionic surfactants.
• non-ionic surfactants that can be used are the water-soluble adducts of ethylene oxide with 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups with polypropylene glycol ethers, alkylene diaminopolypropylene glycol and alkyl polypropylene glycols with 1 to 10 carbon atoms in the alkyl chain, in which the polypropylene glycol ether chain functions as a hydrophobic residue.
• Nonionic surfactants of the amine oxide or sulfoxide type can also be used.
• the foaming power of the surfactants can be increased or decreased by combining suitable types of surfactants. A reduction can also be achieved by adding non-surfactant-like organic substances.
• the liquid, aqueous detergents contain 10 to 50% by weight of surfactants. You can contain an anionic or nonionic surfactant in the amount specified. However, it is also possible to use mixtures of anionic and nonionic surfactants. In such a case, the content of anionic surfactants in the liquid detergent is chosen from 10 to 30% by weight and the content of nonionic surfactants in the liquid detergent from 5 to 20% by weight, based on the total detergent formulation.
• the liquid detergents contain the copolymers to be used according to the invention in amounts of 0.1 to 20, preferably 1 to 10% by weight and water in amounts of 10 to 60, preferably 20 to 50% by weight.
• the liquid detergents may also contain other substances for modification. These include, for example, alcohols, such as ethanol, n-propanol and isopropanol. If used, these substances are used in amounts of 3 to 8% by weight, based on the total detergent formulation.
• the liquid detergents may also contain hydrotropes. This includes compounds such as 1,2-propanediol, cumene sulfonate and toluene sulfonate. If such compounds are used to modify the liquid detergent, their amount, based on the total weight of the liquid detergent, is 2 to 5% by weight. In many cases, addition of complexing agents has also proven to be advantageous for modification.
• Complexing agents are, for example, ethylenediaminetetraacetic acid, nitrilotriacetate and isoserinediacetic acid and phosphonates, such as aminotrismethylenephosphonic acid, hydroxyethanephosphonic acid, ethylenediaminetetraethylenephosphonic acid and their salts.
• the complexing agents are used in amounts of 0 to 10% by weight, based on the liquid detergent.
• the liquid detergents can also contain citrates, di- or triethanolamine, opacifiers, optical brighteners, enzymes, perfume oils and dyes. If these substances are used to modify the liquid detergents, they are present together in amounts of up to 5% by weight.
• the liquid detergents according to the invention are preferably phosphate-free.
• phosphates e.g. Pentasodium triphosphate and / or tetrapotassium pyrophosphate. If phosphates are used, the proportion of phosphates in the total formulation of the liquid detergent is 10 to 25% by weight.
• liquid detergents described above have the advantage over the powder detergents that they are easy to dose and have very good fat and oil dissolving power at greasy soiled laundry at lower washing temperatures.
• Liquid detergents contain high levels of detergent substances that remove dirt from the textile effect fabrics at washing temperatures of 40 to 60 ° C.
• the dispersing properties of polymers have hitherto not been able to be used in aqueous liquid detergents because, as a result of high electrolyte concentrations in the detergents, it was not possible to obtain stable solutions with the polymers. With the copolymers to be used according to the invention, it is now possible to prepare stable aqueous solutions of liquid detergents and to significantly improve the washing properties of liquid detergents.
• the effectiveness of the copolymers to be used according to the invention in liquid detergents is demonstrated in the examples with the aid of the stability of the liquid detergents and the primary and secondary washing action of these detergents.
• the primary washing effect is the actual removal of dirt from the textile material.
• the degree of dirt removal is the difference in the degree of whiteness between the unwashed and the washed textile material after washing. Cotton, cotton / polyester and polyester fabrics with standard soiling are used as the textile test material. After each wash, the whiteness of the fabric in% remission is determined in an Zeiss elrephophotometer.
• Secondary washing is understood to mean the effects which arise from the re-accumulation of the dirt detached from the fabric on the fabric in the wash liquor.
• the secondary washing effect can only take place after several washes, e.g. 3, 5, 10 or even 20 washes become visible, which becomes increasingly gray (noticeable), i.e. Accumulation of dirt from the wash liquor on the fabric.
• standard soiling fabric is washed several times together with white test fabric and the soiled fabric is renewed after each wash.
• the dirt detached from the dirt fabric, which is drawn onto the white test fabric during washing causes a drop in the degree of whiteness that is measured.
• the copolymers to be used in liquid detergents according to the invention or their water-soluble salts can also be used for the formulation of powder detergents.
• the percentages in the examples are percentages by weight.
• the K values were determined according to H. Fikentscher, Cellulose Chemie, Vol. 13, 58 to 64 and 71 to 74 (1932).
• the K values of the copolymers were measured in aqueous solution at 25.degree. C., a pH of 7.5 and a polymer concentration of 1% by weight of the Na salts of the copolymers.
• a solution of 1.44 g of di-tert-butyl peroxide in 8.56 g of xylene is then added over the course of one hour and the reaction mixture is boiled for a further hour at a gentle reflux, then it is cooled to 90 ° C. and 100 is added g of water for the hydrolysis of the anhydride groups and removes the toluene by introducing water vapor as an azeotropic mixture with water until the reactor contents reach a temperature of 100 ° C. After cooling, the copolymer is present as a yellowish, almost clear aqueous solution with a solids content of 39%. After neutralizing to pH 7.5 with sodium hydroxide solution, the copolymer has a K value of 44.
• copolymer 1 The procedure for the preparation of copolymer 1 is repeated, with the only exception that N-octadecylacrylamide is now used instead of N- (1-methyl-1-undecyl) acrylamide. Since the viscosity of the reaction mixture increased greatly during steam distillation, 600 g of water were added. The yellowish copolymer solution thus obtained had a solids content of 11%. The K value of the sodium salt of the copolymer at pH 7.5 was 48.
• the reaction mixture is then heated to boiling at 135 ° C. and a solution of 0.225 g of di-tert-butyl peroxide in 9.775 g of xylene is added within 1 hour. After the peroxide has been added, the reaction mixture is polymerized for a further hour at 135 ° C., then cooled to room temperature and the copolymer is isolated from the low-viscosity suspension by filtering and drying. It is dried at 65 ° C under reduced pressure. The K value of the copolymer neutralized to pH 7.5 with the sodium hydroxide solution is 54.
• a copolymer with a K value of the sodium salt at pH 7.5 of 51 is obtained.
• the reaction mixture is then kept at 135 ° C. for a further hour, then cooled and the copolymer is isolated from the suspension by filtration and subsequent drying at 65 ° C. in vacuo.
• the copolymer is soluble in water and can be neutralized by adding sodium hydroxide solution.
• the K value of the sodium salt is 29.
• the copolymer thus obtainable has a K value in the form of the sodium salt of 37.
• the amines listed in Table 1 are prepared by alkoxylating a C13 / C15 alcohol and then aminating the reaction product.
• Table 1 shows the amounts of amine and the K values of the sodium salt of the copolymers.
• the aqueous copolymer solutions were each treated with an acidic ion exchanger to remove free, unreacted amine.
• the pH was then adjusted to about 7 by adding 50% aqueous sodium hydroxide solution.
• Copolymers 1 to 13 described above were tested in the following two liquid detergent formulations A and B.

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• 1988
  • 1988-11-10 DE DE3838093A patent/DE3838093A1/de not_active Withdrawn
• 1989
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  • 1989-10-27 CA CA002001660A patent/CA2001660A1/fr not_active Abandoned
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