US3919091A - Fabric softening compositions containing quaternary allophanoylmethylammonium compounds - Google Patents

Fabric softening compositions containing quaternary allophanoylmethylammonium compounds Download PDF

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US3919091A
US3919091A US362314A US36231473A US3919091A US 3919091 A US3919091 A US 3919091A US 362314 A US362314 A US 362314A US 36231473 A US36231473 A US 36231473A US 3919091 A US3919091 A US 3919091A
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carbon atoms
weight
water
group
allophanoylmethylammonium
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Hans-Werner Eckert
Peter Nikolaus
Johann Schwarzer
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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    • 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
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
    • C07C275/48—Y being a hydrogen or a carbon atom
    • C07C275/50—Y being a hydrogen or an acyclic carbon atom
    • 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
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/402—Amides imides, sulfamic acids
    • D06M13/432—Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; Carbodiimides; Guanidines, e.g. dicyandiamides
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2352—Coating or impregnation functions to soften the feel of or improve the "hand" of the fabric

Definitions

  • R and R indiriduallx represent hy drogen or alkyl having 1 to 3 carbon atoms and X" represents an anion 01 an inorganic or organic acid; as well as the method of preparation of these quaternar a1lophanoylmethylammonium compounds composi tions containing the same and the method of softening washed textiles utilizing said compounds in the rinse liquor.
  • An object of the present invention is the obtention of softening agent compounds and compositions which effectively soften washed textiles without an adverse effect on the absorptivity of the treated laundry.
  • Another object of the present invention is the development of a quaternary allophanoylmethylammonium compound having the formula wherein R and R are individually members selected from the group consisting of alkyl having l to 24 carbon atoms, alkenyl having l0 to 24 carbon atoms and alkadienyl having to 24 carbon atoms, R is a member selected from the group consisting of alkyl having 1 to 4 carbon atoms, hydroxyalkyl having I to 4 carbon atoms and cyanoalkyl having from 1 to 4 carbon atoms, R and R are individually members selected from the group consisting of hydrogen and alkyl having 1 to 3 carbon atoms, and X represents the anion of an acid selected from the group consisting of inorganic acids and organic acids having I to 4 carbon atoms.
  • a further object of the present invention is the development of a process for the production of the above quaternary allophanoylmethylammonium compounds consisting of the steps of reacting substantially equimolar amounts of an a-haloacylurea having the formula wherein R, and R are individually members selected from the group consisting of hydrogen and alkyl having 1 to 3 carbon atoms, and Hal represents a halogen, with a tertiary amine having the formula wherein R and R are individually members selected from the group consisting of alkyl having 10 to 24 carbon atoms.
  • R is a member selected from the group consisting of alkyl having I to 4 carbon atoms, hydroxyalkyl having 1 to 4 carbon atoms and cyanoalkyl having from 1 to 4 carbon atoms, at a temperature of from 50C to [00C, and recovering said quaternary allophanoylmethylammonium compounds.
  • a yet further object of the present invention is the obtention of a liquid or powdery softening agent composition for washed textiles consisting essentially of a. from 1 to 50% by weight of a quaternary allophanoylmethylammonium compound having the formula wherein R and R are individually members selected from the group consisting of alkyl having l0 to 24 carbon atoms, alkenyl having 10 to 24 carbon atoms and alkadienyl having 10 to 24 carbon atoms, R, is a member selected from the group consisting of alkyl having I to 4 carbon atoms, hydroxyalkyl having 1 to 4 carbon atoms and cyanoalkyl having from I to 4 carbon atoms, R, and R are individually members selected from the group consisting of hydrogen and alkyl having 1 to 3 carbon atoms, and X represents the anion of an acid selected from the group consisting of inorganic acids and organic acids having 1 to 4 carbon atoms.
  • d. the remainder up to by weight of at least one diluent selected from the group consisting of water, and water-soluble or readily water-dispersible liquid and solid carriers.
  • a further object of the invention is the development of a process for the softening of washed textiles which consists of rinsing said washed textiles with water containing from 0.05 to 1.0 gm/] of the above quaternary allophanoylmethylammonium compound.
  • R and R individually represent aliphatic hydrocarbon residues having it) to 24. preferably 12 to 18 carbon atoms.
  • R represents an optionally substituted alkyl residue with l to 4 carbon atoms.
  • R. and R individually represent hydrogen or an alkyl residue with l to 3 carbon atoms.
  • X represents an anion of acid. especially the chloride anion.
  • the invention relates to a quaternary allophanoylmethylammonium compound having the formula wherein R and R are individually members selected from the group consisting of alkyl having it) to 24 car bon atoms. alkenyl having it) to 24 carbon atoms and alkadienyl having it] to 24 carbon atoms.
  • R is a member selected from the group consisting of alkyl having I to 4 carbon atoms. hydroxyalkyl having 1 to 4 carbon atoms and cyanoalkyl having from 1 to 4 carbon atoms.
  • R and R are individually members selected from the group consisting of hydrogen and alkyl having 1 to 3 carbon atoms, and X represents the anion of an acid selected from the group consisting of inorganic acids and organic acids having 1 to 4 carbon atoms.
  • Antimicrobial substances and optical brighteners can be readily incorporated with the new textile softeners in liquid and solid compositions.
  • the aliphatic hydrocarbon residues R. and R in the Formula l may be straight or branched chain. saturated or unsaturated residues of synthetic or natural origin. Specially preferred residues R and R are the straightchain alkyls. for example. decyl. dodecyl. tetradecyl.
  • the residues R and R may be derived from naturally occurring fatty acids.
  • substituent R alkyls having l to 4 carbon atoms. such as methyl. ethyl. propyl or butyl are suitable. as well as substituted alkyl residues such as hydroxyalkyl and cyanoalkyl. for example. Z-hydroxyethyl or 2-cyanoethyl. Methyl is of particular practical interest.
  • the residues R. and R may be the same or different. They preferably represent hydrogen or methyl or ethyl.
  • the anion X limited by the process of preparation further described below. is especially a halide anion. preferably the chloride anion.
  • the quaternary ammonium compounds of Formula I according to the inven- 4 tion. however. can be converted in known way into salts with other anions of inorganic acids and organic acids. such as sulfates. borates. phosphates, perchlorates. and salts of organic acids. if this is desired. for example. to obtain a better processability.
  • the new substances of Fonnula l are solid at normal temperature. readily soluble or dispersible in water. they are also very soluble in the lower alcohols such as methanol. ethanol and isopropyl alcohol.
  • the invention further relates to a process for the preparation of the new substances of Formula I.
  • a process for the preparation of the new substances of Formula I In this process about 1 mol of an a-haloacylurea of Formula lla Hal CR..R,-.CONHCONH (llu) is reacted with 1 mol of a tertiary amine of Formula llb NR
  • the product is obtained after removing the solvent e.g. by distillation. and is generally used in this form for technical purposes. In some cases. a purification by re dissolving or recrystallization can be utilized. for example. from acetone. ethyl acetate. acetonitrile. isopropyl alcohol, or mixtures of these solvents with one another. optionally with use of active charcoal or other adsorbents.
  • condensation products of an a-halocarboxylic acid halide with urea for example. chloroacetylurea. a-chloropropionylurea. oz-bromobutyrylurea. a chloroisobutyrylurea and so on. are used as the ahaloacylurea of Formula llu. Chloroacetylurea is preferred where R. and R are hydrogen.
  • the tertiary aliphatic amines of Formula llb used in the process according to the invention are. for examle. didodecylmethylamine. ditetradecylmethylamine. Elihexadecylmethylamine. dioctadecylmethylamine. didodecyl-( Z-hydroxyethyl l-amine. ditetradecylisopropylamine. didodecylisobuty'lamine. etc.
  • Tertiary aliphatic amines of Formula llb in which R, and R represent residues derived from fatty acids of natural origin are also of practical interest. for example. coconut fatty acid. tallow fatty acid. soya fatty acid. rape oil fatty acid. or their hydrogenation products. Such tertiary amines are. for example. ditallow-alkylmethylamine. di-coconut-alkylrnethylamine, etc.
  • organic solvents which may be used in the process of preparations are. for example. the lower alcohols such as methanol. ethanol. isopropyl alcohol. butanol. and also acetonitrile. glycol. ethyleneglycol-monomethyl and -dimethyl ethers. dimethylformamide and dimethylsulfoxide. and possibly mixtures of these solvents with water.
  • the lower alcohols such as methanol. ethanol. isopropyl alcohol. butanol. and also acetonitrile.
  • N.N-Dicoconut-alkyl-N-methyl-Nallophanoylmethylammonium chloride 7, NN-Didodecyl-NJI-hydrox eth l)-N-allophanoylmethylammonium chloride; 8. NA-Ditetradecyl'Nisopropyl-N-1illophz
  • N.N-Didodecyl-X-isohutyLNallophanoylmethylammonium chloride N,N-Dieicosyl Nmethyl-N-allophanoylmethylammnnium chloride: N,N-Didocosyl-N-methyl-Nallophanoylmethylammonium chloride: 12.
  • the further treatment of the laundry with the compounds of Formula 1 may be effected in various ways depending on the drying process, which is to be used.
  • the washed laundry can be directly sprayed with a dispersion of the active substance or the latter may be brought into contact with the washed laundry by way of a carrier, for example by spraying the inside walls of the drier with the dispersion of active substance before the drier is charged with the wash or by the addition to the charge of a carrier of large surface area saturated with the dispersion of active substance, whereby the textile softener is absorbed on the washed goods during the drying process.
  • the washing is generally hung out to dry, therefore the application of the softener in the last rinsing bath in a washing process when done by hand, and especially by machine washing, is most commonly used.
  • this procedure can be followed where the wash is dried in a drier also.
  • the compound of Formula 1 is preferably used in the rinsing bath in amounts from 0.05 to 1.0 gm/liter, especially from 0.1 to 0.5 gm/liter.
  • rinsing bath which substances are usable for the aftertreatment of washed laundry, such as optical brighteners, anti-microbial active agents, souring agents, sequestering agents, perfumes and dyes, etc. At least part of these substances should be acidic, and the amount of the acidic substances, particularly of the souring and sequestering agents is selected so that the rinsing bath has a neutral to weakly acidic pH range.
  • the invention relates to the use of the compounds of Formula according to the invention as textile softeners in washing after-treatment compositions.
  • Said washing after-treatment composition is more particularly a liquid or powdery softening agent composition for washed textiles consisting essentially of a. from 1 to 50% by weight of a quatemary allophanoylmethylammonium compound having the formula wherein R and R are individually memebers selected from the group consisting of alkyl having 10 to 24 carbon atoms. alkenyl having 10 to 24 carbon atoms and alkadienyl having 10 to 24 carbon atoms.
  • R is a member selected from the group consisting of alkyl having 1 to 4 carbon atoms, hydroxyalkyl having 1 to 4 carbon atoms and cyanoalkyl having from 1 to 4 carbon atoms
  • R, and R are individually members selected from the group consisting of hydrogen and alkyl having I to 3 carbon atoms
  • X represents the anion of an acid Selected from the group consisting of inorganic acids and organic acids having 1 to 4 carbon atoms.
  • d. the remainder up to by weight of at least one diluent selected from the group consisting of water. and water-soluble or readily water-dispersible liquid-and solid carriers.
  • the new substances can be used as textile softeners in pulverulent or liquid washing after-treatment compositions.
  • Suitable liquid carriers or diluents are water and water-soluble organic solvents from the group of lower alcohols containing 1 to 5 carbon atoms; preferably alkanols having 1 to 5 carbon atoms, for example, methanol, ethanol, propanol, isopropyl alcohol, butanol, amyl alcohol, lower ketones, preferably alkanones having 3 to 6 carbon atoms, such as acetone and methylethylketone and the ethyleneand diethylene glycols and their monomethyl or dimethyl, or monoethyl or diethyl ethe rs, as well as mixtures of the same with water.
  • lower alcohols containing 1 to 5 carbon atoms preferably alkanols having 1 to 5 carbon atoms, for example, methanol, ethanol, propanol, isopropyl alcohol, butanol, amyl alcohol, lower ketones, preferably alkanones having 3 to 6 carbon atoms, such as acetone and methyl
  • Solid carriers or diluents which may be used are readily watersoluble or water-dispersible inert inorganic or organic compounds especially from the group comprising urea. acetamide, biuret, sodium sulfate. solid polyethylene glycols and, optionally, solid forms of the below listed acid additives and acid sequestering agents.
  • the other components of the after-treatn agents according to the invention consist essentially of dispersing agents, especially non-ionic dispersing agents, optical brighteners, antimicrobial active agents, acid additives or souring agents, solution aids, perfumes and dyestuffs.
  • the quaternary allophanoylmethylammonium compounds, according to the invention, dissolved in organic solvents, may be sprayed on the moving solid carrier substances.
  • carrier substances with the largest possible surface and a low bulk weight, for example a bulk weight of 100 to 700 gm/l are preferably used. Products of such bulk weight are obtained, for example, by calcining inor ganic salts containing water of crystallization.
  • the active substances can also be mixed with the molten urea. to which. means for lowering the melting point has been added. and the melt converted into a powder. In all cases the powder properties can be improved by incorporation of small quantities of substances with a large surface a eu as. for example. microcrystalline silicic acid. magnesium silicate. and so on.
  • composition of the powdery washing after-treat ment agents for laundry of the invention lies generally in the range of the following formulation based on the anhydrous substances:
  • a dispersing agent preferably a nonionic dispersing agent.
  • the powdery agents of the invention are utilized in such amounts that the concentration of the textile softener is in the range offrom 0.05 to 1.0 gm/l of the aqueous treatment liquor.
  • composition of particularly interesting liquid washing after-treatment compositions in which the above-defined new substances according to the invention are utilizable.
  • dispersing agents preferably non-ionic dispersing agents.
  • washing after-treatment agents 0 to l0%. preferably 0.3 to 7.5% by weight of other usual components of washing after-treatment agents.
  • At least one of the following components may be present in the given amounts. referred to the total composition. as the other usual components of washing aftertreatment agents.
  • liquid agents are prepared by mixing the com ponents.
  • the liquid and solid agents according to the invention are distinguished by a good dispersibility in cold water.
  • fabrics hardened by washing. particularly cotton terry cloth. become soft and nappy.
  • an undesirable static charging of the textiles particularly those of synthetic fibers. is largely prevented.
  • washing aftertreatment agents of the invention are described below. in addition to the quaternary allophanoylmethylammonium compounds and the carrier substance. and are described more particularly by their various classes.
  • Suitable dispersing agents which may be contained in the liquid and pulverulent washing after-treatment compositions are especially the non-ionic surface-active substances. referred to below as nonionics. These include products which owe their hydrophilic properties to the presence of polyether chains. ami neoxide. sulfoxide or phosphine oxide groups. alkylolamide groups as well quite generally to an excess of hydroxyl groups.
  • nonionics contain in the molecule at least one hydrophobic radical of 8 to 26. preferably l0 to 20 and particularly [2 to l8 carbon atoms. and at least one nonionic watcr-solubilizing group.
  • the preferably saturated hydrophobic radical is mostly of an ali phatic.
  • connecting member for instance. benzene rings. carboxylic acid ester or carbonamide groups. ether-like or ester-like bound radicals of polyhydric alcohols. such as those of the ethylene glycol. the propylene glycol. the glycerine or of corresponding polyether radicals. are of interest.
  • ethylene oxide and/or glycide to fatty alcohols. alkylphenols. fatty acids. fatty amines. fatty acid or sulfonic acid amides having the above hydrophobic radicals.
  • These nonionics may contain from 4 to 100. preferably 6 to 40 and particularly 8 to 20 ether groups. above all ethylene glycolether groups. per molecule. in addition. in these polyether chains or at their end. propylene or butyleneglycolether groups or polyether chains may be present.
  • non-ionic surface-active compounds are the water-soluble products of the addition of ethylene oxide to polypropylene glycol Pluronics or to al kylenediaminepolypropylene glycol Tetronics. They are obtained from polypropyleneglycols. themselves water-insoluble. or from water-insoluble propoxylated lower aliphatic alcohols containing 1 to 8. preferably 3 to 6 carbon atoms. or from water-insoluble propoxylated alkylenediamines. These water-insoluble (i.e. hydrophobic) propylene oxide derivatives are con- .verted into the said non ionics by ethoxylation until the products are water-soluble. Finally. the reaction products of the above-mentioned aliphatic alcohols with propylene oxide known as UcomFluidsome of which are still water-soluble. are utilizable as nonionics.
  • fatty acid or sulfonic acid alkylolamides which are derived. for instance. from mono or diethanolamine, from dihydroxypropylamine or other polyhydroxyalkylamines.
  • glycamines tives of the diaminostilbene-disulfonic acid are compounds according to formula lll:
  • nonionics are in the class of useable nonionics. They can be replaced by amides of higher primary or secondary alkylamines and polyhydroxy carboxylic acids.
  • Nonionic surface-active compounds of the amineoxide type are also utilizable.
  • the nonionic surface-active amincoxides include, for example, the products derived from higher tertiary amines having a hydrophobic alkyl residue and two shorter alkyland/or alkylol residues containing up to 4 carbon atoms each.
  • nonionic dispersing agents optionally suitable are also water-soluble or water-emulsifiable or dispersible compounds, which contain no hydrophobic radicals in the sense of the above-described nonionic surface-active agents or in which the nature or the number ofhydrophilic groups is insufficient to attain a complete watensolubility.
  • the former includes compounds such as solid or liquid polyethylene glycols, ethylene oxide adducts of glycerine and other polyalcohols, etc.
  • the latter include, for example. partial fatty acid glycerides or water-insoluble or not completely water-soluble alkoxylation products, for example those with 2 to 5 ethylene glycolether residues in the molecule.
  • Useful water-soluble organic solvents are the lower alcohols having 1 to 5 carbon atoms, as for example, methanol, ethanol, propanol, isopropyl alcohol, butanol, amyl alcohol, and also the lower ketones as for example, acetone and methylethylketone, as well as ethyleneglycol and diethyleneglycol and their monoor di-methyl or ethyl ethers.
  • lsopropyl alcohol is of special practical interest.
  • nocuous to the fibers to be treated with 2 to 8 carbon v atoms optionally in the form of their slightly acidic water-soluble salts, such as their alkali metal salts, are suitable as acid additives or souring agents, such as amidosulfonic acid, urea compounds of orthophosphoric acid, boric acid, oxalic acid, lactic acid, glycolic acid, citric acid, tartaric acid, benzoic acid, phthalic acid, gluconic acid. acetic acid and propionic acid as well as benzene, toluene or xylene sulfonic acids, sulfoacetic acid or sulfobenzoic acids.
  • the acid additives are hydroxyalkanoic acids having 2 to 8 carbon atoms, hydroxyalkanedioic acids having 3 to 8 carbon atoms, dihydroxyalkanedioic acids having 4 to 8 carbon atoms, hydroxyalkanetrioic acids having 4 to 8 carbon atoms and alkanoic acids having 2 to 8 carbon atoms.
  • Urea and lower carboxylic acid amides preferably lower alkanoic acid amides, for example, acetamide, and the potassium salts of benzene, toluene, or xylene sulfonic acids, sulfoacetic acid or sulfobenzoic acid may be used as solution aids.
  • the useable brighteners are mostly, if not exclusively. derivatives of aminostilbene-sulfonic acid or diaminostilbene-sulfonic acid, diarylpyrazolines, carbostyril, l ,2-di-( Z-benzoxazolyl )-or l ,2-di-( Z-benzimidazolyl)-ethylene, benzoxazolyl-thiophene and coumarins.
  • Examples for brighteners from the class of the deriva- In the formula R and R signify alkoxy groups, amino groups or residues of aliphatic, aromatic or heterocyclic, primary or secondary amines, or residues of aminosulfonic acids, while aliphatic residues present in the above groups preferably contain l to 4 and especially 2 to 4 carbon atoms, and in the hcterocyclic ring systems. five-or sixmembered rings are usually of interest. Aniline, anthranilic acid or anilinesulfonic acid residues are preferred as the aromatic amines.
  • Brighteners derived from diaminostilbenesulfonic acid are mostly used as cotton brighteners.
  • the following products derived from the above formula [II in which R represents the residue -NHC.,H and R may represent the following residues, are at present on the market.
  • Diarylpyrazolines of Formulas IV and V belong to the polyamide brighteners, of which again a few have a certain affinity for cotton fibers:
  • R;, and R represent hydrogen atoms. or alkyl or aryl residues possibly substituted by carboxyl.
  • R and R represent hydrogen or short-chain alkyl residues.
  • Ar and Ar represent aryl residues such as phenyl diphenyl or naphthyl. which may carry further substituents such as hydroxy. alkoxy. hydroxyalkyl. amino. alkylamino. acylamino. earboxyl. carbo ⁇ y1ic acid ester. sulfonic acid. sulfonamide and sulfone groups or halo gen atoms.
  • Brighteners of this type found at present on the market are derived from the formula V. and the residue R may represent the groups C1.
  • SO NH SO- ,CH Chand COOCH -CH OCH while the residue R in all cases represents a chlorine atom.
  • Cyano-anthracene is also on the market as a polyamide brightener.
  • aliphatic or aromatic substituted aminocoumarins belong to the polyamide brighteners, for example 4methyl-7-dimethy1aminoor 4-methyl7-diethylaminocoumarin.
  • Further useful polyamide brighteners are the compounds l-(benzimidazo1yl-2')-2-(l ⁇ lhydroxyethyl-benzimidaZolyl-2'l-ethylene and LN- ethyl-3 phenyl-7-diethy1aminocarbostyril.
  • Suitable brighteners for polyester and polyamide fibers are the compounds 2,5-di-( benzoxazolyl-Z )-thiophene. 2( 2 benzoxazoly 1 )-naphtho-[ 2 3-b l-thiophene and 1,2-di- (5 '-methy1-benzoxazo1y1-2' )-ethy lene.
  • the brighteners together with other components of the products of the invention are present as aqueous solutions or pastes and are converted into a solid state by hot drying. It is advisable to incorporate at least 0.1%. preferably 0.2 to 1% by weight of the solid products of organic complex-forming substances for stabilizing the brighteners.
  • Anti-microbial active substances are here understood as bactericidal or bacteristatic or fungicidal or fungistatic acting compounds. These active substances should be water-soluble as such. or in the form of their salts.
  • the anti-microbial active substances. usable according to the invention. are mostly quaternary ammonium compounds. particularly those which contain, in addition to a long-chain aliphatic and two short-chain aliphatic hydrocarbon radicals, an organic radical in the molecule, either aromatic residue connected over an aliphatic carbon atom to the nitrogen atom or an aliphatic residue with double bonds.
  • anti-microbial quaternary ammonium compounds are the following: dimethyl-benzyl-dodecyl-ammonium chloride, dimethyl-benzyl-tetradecylammonium chlo' ride. dimethyl-( ethylbenzyl )-dodecyl-am monium chloride. dimethyl-benzy1-decyl-ammonium bromide, diethylbenzyl-dodecyl-ammonium chloride, diethylbenzyl'octylammonium chloride. dibutyl-al1yl-, methylethy1-benZy1-. ethyl-cyclohexyl-a1lyland ethyl-crotyl diethylaminoethyl-. dodecyl-ammonium chlorides.
  • phenolic compounds of the type of the halogenated phenols with l to 5 halo substituents particularly chlorinated phenols; alky1-. CycloalkyL. aralkyland phenylphenols with 1 to 12 carbon atoms in the alkyl radical and with l to 4 halo substituents. particularly chlorim: and bromine in the molecule: alkylene lais phenols,
  • hydroxy benzoic acids or their esters and amides particularly anilides which may be substituted in the benzoic acid and/or aniline radical especially by 2 or 3 halogen atoms and/or trifluoromethyl groups; 0- phenoxyphenols which may be substituted by l to 7. preferably 2 to 5 halogen atoms and/or the hydroxyl. cyano. carbomethoxy. and carboxyl group or by lower alkyl.
  • a particularly preferred derivative of the class of o-phenoxyphenols is 2-hydroxy-2, 4.4'-trichlorodiphenyl ether.
  • EXAMPLE l N.N-Didodecyl-N-methyl-N-allophanoylmethylammonium chloride 41.1 gm (0.3 mol) of chloroacetylurea. were suspended in a solution of 1 10.2 gm (0.3 mol) of didodecylmethylamine in 500 ml of isopropyl alcohol and the mixture was heated for 30 hours at about C (reflux temperature). After removing the solvent in vacuo. the reaction product was a highly viscous oil. which solidified on standing and was obtained as a solid having a melting point of 133C after recrystallizing from ethyl acetate.
  • sub- EXAMPLE sequently centrifuged, dried and ironed between filter N.N-Ditallow-alkyl-N-methyl-N-allophanoylmethylam- H g?" g g i?$ i g f g monium Chloride: ml lty or ours. t cse strips. cm ong an cm wide, were suspended with their lower ends in distilled ldemfied by mfmred p pywater and the rise in height d of the water after a time 'of l. 2. 5. 10. and minutes were measured.
  • the absorption time is, according to the true dimension (sec/cm l, a reciprocical speed. An increase. therefore. corresponds a decrease in the absorptivity of the fabric.
  • lf 1,- is designated as the absorption time of the fabric rinsed with the preparation i and t the absorption time of the fabric rinsed with water.
  • absorption value that is the residual absorptivity of the soft-rinsed fabric. referred to the sample treated with water I 100%, the following equation is used.
  • Examples 8 to 10 describe liquid washing after-treatment compositions. in which the substances of Formula I are used according to the present invention.
  • the substance of Formula I was converted at 50 to 60C into a homogeneous melt with the dispersing agent and optionally an organic solvent as well as in some cases other additives.
  • the acid and optionally the optical brightener were dissolved in water and this aqueous solution was added with vigorous stirring to the abovementioned melt.
  • the preparations so obtained are marked by a good pourability and dispers ibility in water. Perfumes and dyestuffs may be mixed with the preparations.
  • EXAMPLE 8 6.0% by weight of N,N-Didodecyl-N-methyl-Nal
  • EXAMPLE 9 6.0% by weight of N.N-Ditetradecyl-N-allophanoylmethylammonium chloride;
  • EXAMPLE 10 6.0% by weight of N.N-Dicoconut-alkyl-Nanethyl-N- allophanoylmethylammonium chloride; 1.5% by weight of an adduct of cetyl-oleyl alcohol mol ethylene oxide; 0. l7r by weight of cotton brightener of Formula III in which R, signifies the anilinoand R the dihydroxyethylamino residue; 0.3% by weight of 2-hydroxy-2',4,4'-trichlorodiphen ylether; 0.5% by weight of citric acid; 5.0% by weight of isopropyl alcohol; Remainder water.
  • Example 2 describes the preparation and composition of pulverulent washing after-treatment agents for laundry according to the invention.
  • EXAMPLE l l Pulverulent washing after-treatment composition 15.0% by weight of N.N-Di-tallow-alkyl-N-methyl-N- allophanoylmethylammonium chloride;
  • the preparation according to Example 11 was prepared as follows: the textile-softening compound and the nonionic dispersing agent were melted to a homogenous mixture at 50 to 60C. Simultaneously, the organic acid and the carriers were dissolved in water, preheated to 50C, and the above-named melt was stirred into this solution. The amounts were utilized so that l kg of all the ingredients of the washing after-treatment agent of the above composition was allotted to 5 liters of water. The dispersion thus obtained was atomized in a spray tower at [50C. A white, fine-grained and readily pourable powder resulted. To the finished preparation perfumes and anti-microbial active substances may be added.
  • composition of Example 11 could also be prepared as follows:
  • the washing after-treatment agents for laundry according to the invention are marked by a rapid dispersibility and distribution in cold water, so that the action of the textile softener, for example on use in the last rinsing cycle of a washing machine, is effective.
  • the treatment with the preparations of the invention at a concentration of 0.3 gm of the textile softener per liter of rinsing bath already leads to a full and soft handle of the finished textiles. which are also marked by a good absorption capacity.
  • a liquid or powdery softening agent composition for washed textiles consisting essentially of a. from 1 to 50% by weight of a quaternary allophanoylmethylammrmium compound having the formula wherein R and R are individually members selected from the group consisting of alkyl having [0 to 24 carbon atoms, alkenyl having 10 to 24 carbon atoms and alkadienyl having 10 to 24 carbon atoms, R is a menr ber selected from the group consisting of alkyl having 1 to 4 carbon atoms, hydroxyalkyl having 1 to 4 carbon atoms and cyanoalkyl having from 1 to 4 carbon atoms, R 4 and R are individually members selected from the group consisting of hydrogen and alkyl having I to 3 carbon atoms, and X represents the union of an acid selected from the group consisting of inorganic acids and organic acids having I to 4 carbon atoms,
  • nonionic surface-active dispersing agent selected from the group consisting of a water-soluble dispersing agent and a watendispersible dispersing agent
  • diluent selected from the group consisting of water, and water-soluble or readily water-dispersible liquid carriers selected from the group consisting of alkanols having 1 to 5 carbon atoms, alkanones having 3 to 6 carbon atoms, and ethylene glycol and diethylene glycol and their monomethyl, dimethyl, monoethyl and diethyl ethers, and solid, inert, water-soluble or readily water-dispersible inorganic and organic compound carriers.
  • diluent selected from the group consisting of water, and water-soluble or readily water-dispersible liquid carriers selected from the group consisting of alkanols having 1 to 5 carbon atoms, alkanones having 3 to 6 carbon atoms, and ethylene glycol and diethylene glycol and their monomethyl, dimethyl, monoethyl and diethyl ethers, and solid, inert, water-soluble or readily water-dispersible inorganic and organic compound carriers.
  • liquid or powdery softening agent composition of claim 1 having a further component of from 0.2 to 6% of an acid additive selected from the group consisting of inorganic acids innocuous to the fibers to be treated.
  • organic acids having from 2 to 8 carbon atoms innocuous to the fibers to be treated and their slightly acidic water-soluble salts.
  • composition of claim I wherein said diluent is selected from the group consisting of water, said liquid 19 carriers and mixtures thereof in an amount of from 74 to 97.8% by weight.
  • composition of claim 1 wherein said diluent is a finely-divided solid selected from the group consisting of inert water-soluble. finely-divided solids and inen. readily water-dispersible. finely-divided solids. in an amount of from 40 to 98.8% by weight.
  • a liquid softening agent composition for washed textiles consisting essentially of a. from 2 to by weight of a quaternary a1lophanoylmethylammonium compound having the formula wherein R and R are individually members selected from the group consisting of alkyl having 10 to 24 carbon atoms. alkenyl having 10 to 24 carbon atoms and alkadienyl having 10 to 24 carbon atoms. R is a member selected from the group consisting of alkyl having 1 to 4 carbon atoms, hydroxyalkyl having 1 to 4 carbon atoms and cyanoalkyl having from 1 to 4 carbon atoms. R, and R are individually members selected from the group consisting of hydrogen and alkyl having l to 3 carbon atoms, and X" represents the anion of an acid selected from the group consisting of inorganic acids and organic acids having 1 to 4 carbon atoms,
  • said acid additives selected from the group consisting of inorganic acids innocuous to the fibers to be treated, organic acids having from 2 to 8 carbon atoms innocuous to the fibers to be treated and their slightly acidic water-soluble salts.
  • water-soluble organic solvents selected from the group consisting of alkanols having 1 to 5 carbon atoms. alkanones having 3 to 6 carbon atoms. and ethyleneglycol and diethylene glycol and their monomethyl. dimethyl. monoethyl and diethyl ethers. and
  • a powdery softening agent composition for washed textiles consisting essentially of 20 a. from 5 to 25% by weight of a quaternary allophanoylmethylammonium compound having the formula wherein R and R are individually members selected from the group consisting of alkyl having 10 to 24 carbon atoms. alkenyl having 10 to 24 carbon atoms and alkadienyl having 10 to 24 carbon atoms, R is a member selected from the group consisting of alkyl having 1 to 4 carbon atoms. hydroxyalkyl having 1 to 4 carbon atoms and cyanoalkyl having from 1 to 4 carbon atoms. R and R are individually members selected from the group consisting of hydrogen and alkyl having 1 to 3 carbon atoms. and X represents the anion of an acid selected from the group consisting of inorganic acids and organic acids having 1 to 4 carbon atoms,
  • acid additives selected from the group consisting of inorganic acids innocuous to the fibers to be treated.
  • organic acids having from 2 to 8 carbon atoms innocuous to the fibers to be treated and their slightly acidic water-soluble salts.
  • a process for the softening of washed textiles which consists of rinsing said washed textiles with water containing from 0.05 to 1.0 gm/l of a quaternary allophanoylmethylammonium compound having the formula wherein R. and R are individually members selected from the group consisting of alkyl having 10 to 24 carbon atoms. alkenyl having 10 to 24 carbon atoms and alkadienyl having 10 to 24 carbon atoms, R is a member selected from the group consisting of alkyl having 1 to 4 carbon atoms.
  • R and R are individually members selected from the group consisting of hydrogen and alkyl having 1 to 3 carbon atoms.
  • X represents the anion of an acid selected from the group consisting of inorganic acids and organic acids having 1 to 4 carbon atoms. drying said textiles and recovering said softened, washed tex-

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  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4281186A (en) * 1978-12-27 1981-07-28 Chemische Fabrik Stockhausen & Cie Acrylyl and methacrylyl ureas containing quaternary groups, process for their preparation and their use in the preparation of polymers
US5206080A (en) * 1991-02-13 1993-04-27 Tree Extracts Research Association Fragrant non-hollow core-in-sheath type composite staple fiber and textile material containing same
US5250077A (en) * 1987-04-28 1993-10-05 Kanebo Co., Ltd. Silk fiber having good abrasion resistance and good light resistance and methods for the preparation thereof
US5288905A (en) * 1988-10-07 1994-02-22 G. D. Searle & Co. Glycyl urea derivatives as anti-convulsants
WO2001034743A1 (en) * 1999-11-05 2001-05-17 The Procter & Gamble Company Aqueous fabric softener compositions containing highly unsaturated active and chelant

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2459354C2 (de) * 1974-12-16 1986-03-27 Hoechst Ag, 6230 Frankfurt Waescheweichspuelmittelkonzentrat mit desinfizierenden eigenschaften
DE3122482A1 (de) * 1980-06-06 1982-04-08 L'Oreal, 75008 Paris Quarternaere bis-ammoniumderivate enthaltende mittel zur behandlung keratinischer materie und nicht-keratinischer, natuerlicher oder synthetischer textilstoffe, verfahren zur anwendung der genannten mittel sowie neue hierbei verwendete verbindungen
US4427558A (en) 1981-05-08 1984-01-24 Lever Brothers Company Fabric conditioning materials
JP4863783B2 (ja) * 2006-06-26 2012-01-25 株式会社竹中工務店 鋼管仕口構造及び鋼管接合方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2253773A (en) * 1937-04-20 1941-08-26 Geigy Ag J R Treating, especially softening, cellulosic textile materials
US3065110A (en) * 1959-11-24 1962-11-20 Bayer Ag Process for preventing electrostatic charges on synthetic high polymers
US3256180A (en) * 1962-08-14 1966-06-14 Little Inc A Fabric softener compositions
US3644204A (en) * 1967-08-14 1972-02-22 Henkel & Cie Gmbh Agent for the post-treatment of washed laundry

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2203506A (en) * 1937-06-18 1940-06-04 Ici Ltd Nitrogen-containing organinc compound

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2253773A (en) * 1937-04-20 1941-08-26 Geigy Ag J R Treating, especially softening, cellulosic textile materials
US3065110A (en) * 1959-11-24 1962-11-20 Bayer Ag Process for preventing electrostatic charges on synthetic high polymers
US3256180A (en) * 1962-08-14 1966-06-14 Little Inc A Fabric softener compositions
US3644204A (en) * 1967-08-14 1972-02-22 Henkel & Cie Gmbh Agent for the post-treatment of washed laundry

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4281186A (en) * 1978-12-27 1981-07-28 Chemische Fabrik Stockhausen & Cie Acrylyl and methacrylyl ureas containing quaternary groups, process for their preparation and their use in the preparation of polymers
US5250077A (en) * 1987-04-28 1993-10-05 Kanebo Co., Ltd. Silk fiber having good abrasion resistance and good light resistance and methods for the preparation thereof
US5288905A (en) * 1988-10-07 1994-02-22 G. D. Searle & Co. Glycyl urea derivatives as anti-convulsants
US5206080A (en) * 1991-02-13 1993-04-27 Tree Extracts Research Association Fragrant non-hollow core-in-sheath type composite staple fiber and textile material containing same
WO2001034743A1 (en) * 1999-11-05 2001-05-17 The Procter & Gamble Company Aqueous fabric softener compositions containing highly unsaturated active and chelant

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JPS4948705A (enrdf_load_stackoverflow) 1974-05-11
DE2224553A1 (de) 1973-12-13
IT987434B (it) 1975-02-20
NL7305593A (enrdf_load_stackoverflow) 1973-11-21
FR2190807A1 (enrdf_load_stackoverflow) 1974-02-01
BR7303567D0 (pt) 1974-07-25
AT321317B (de) 1975-03-25
BE799658A (fr) 1973-11-19
FR2190807B1 (enrdf_load_stackoverflow) 1976-11-12
ZA733370B (en) 1974-04-24
GB1427601A (en) 1976-03-10

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