US3795610A - Powdery softening rinsing agent compositions - Google Patents

Powdery softening rinsing agent compositions Download PDF

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US3795610A
US3795610A US00213721A US3795610DA US3795610A US 3795610 A US3795610 A US 3795610A US 00213721 A US00213721 A US 00213721A US 3795610D A US3795610D A US 3795610DA US 3795610 A US3795610 A US 3795610A
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H Eckert
C Werner
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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
    • 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
    • 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

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  • a powdery softening rinsing agent composition comprising a combination of (1) an unsaturated carboxylic acid ester of the formula wherein R and R are selected from the group consisting of alkyl and alkenyl having from 10 to 24 carbon atoms, R is alkyl having 1 to 4 carbon atoms, A is selected from the group consisting of alkenyl and alkenylene having from 2 to 5 carbon atoms, X is an anion selected from the group consisting of halide and the anion of an organic, non-surface-active acid and n is an integer of 1 or 2, (2) non-ionic dispersing agents, (3) at least one solid diluent and (4) optionally other customary ingredients of solid softening rinsing agents for washed laundry, where component (1) is present (a) in a homogenous mixture with the other components, or (b) in
  • liquid softening rinsing agents for laundry which contain as active ingredient difattyalkyldimethylammonium salts, and generally present in the form of an aqueous dispersion. It is known, however, that such cationic softening rinsing agents, even in a strict adherence to the application directions, affect adversely the absorptivity of the treated laundry.
  • a liquid softening rinsing agent composition comprising (A) From 1% to 25% by weight of an unsaturated carboxylic acid ester of the Formula I wherein R and R are selected from the group consisting of alkyl and alkenyl having from to 24 carbon atoms, R is alkyl having 1 to 4 carbon atoms, A is selected from the group consisting of alkenyl and alkenylene having from 2 to 5 carbon atoms, X is an anion selected from the group consisting of halide and the anion of an organic, non-surface-active acid and n is an integer of 1 or 2,
  • An object of the present invention is the obtention of powdery softening rinsing agent compositions incorporating the textile softening unsaturated carboxylic acid esters of Formula I which effectively soften washed textiles without an adverse effect on the absorptivity of the treated laundry and which have good dispersibiilty in cold water.
  • Another object of the present invention is the obtention of powdery softening rinsing agent compositions for washed textiles containing (1) from 1% to 50% by weight of an unsaturated carboxylic acid ester of the formula wherein R and R are selected from the group consisting of alkyl and alkenyl having from 10 to 24 carbon atoms, R is alkyl having 1 to 4 carbon atoms, A is selected from the group consisting of alkenyl and alkenylene having from 2 to 5 carbon atoms, X is an anion selected from the group consisting of halide and the anion of an organic, non-surface-active acid and n is an integer of 1 or 2, (2) from 0.2% to 10% by weight of at least one nonionic surface-active dispersing agent, (3) from 0 to 25% by weight of other customary ingredients of solid softening rinsing agents for washed laundry and (4) the remainder up to 100% by weight of at least one solid diluent carrier compatible with rinsing agents for washed
  • a powdery softening rinsing agent for washed laundry consisting of a combination of esters of unsaturated carboxylic acids of the Formula I wherein R and R are alkenyl, or preferably saturated alkyl with 10 to 24, preferably 12 to 20 carbon atoms,
  • R is a lower alkyl with 1 to 4 carbon atoms, particularly methyl
  • A is an alkenyl or alkenylene with 2 to 5 carbon atoms
  • X is a halide, particularly chloride or bromide and/or the anion of an organic, non-surface-active acid and n is the number 1 or 2
  • esters of unsaturated carboxylic acids, the textile softening active substance is present in the composition (a) in a homogenous mixture with the other components, or (b) in a finely-divided form on the surface of the solid carrier particles of the diluent, and where the particles according to (a) and (b) may be cornbined as agglomerates.
  • the alkyl radicals R and R may be straight-chain or branched, and can be, for instance, lauryl, myristyl, cetyl, oleyl, stearyl, arachidyl, behenyl, lignoceryl, etc.
  • alkyl radicals R and R which are derived from natural fatty acids, particularly from hardened tallow fatty acids or coconut fatty acids.
  • A is an alkenyl
  • it can be, for instance, vinyl, allyl, isopropenyl, l-propenyl, 2-butenyl, 1,3-butadienyl, etc.
  • a is an alkenylene it can be, for instance, vinylene, methylvinylene, 1,4-butadienylene-(1,3), etc.
  • the radical A may be present both in the cis and in the trans form.
  • souringand sequestering agents As diluents, easily water-soluble or easily, in water dispersible, inert solid carriers, such as, urea, acetamide, biuret, sodium sulfate, solid polyethylene glycols and, optionally, solid forms of the below listed souringand sequestering agents come into consideration.
  • the other ingredients of the powdery softening rinsing agents for laundry of the invention are particularly nonionic dispersing agents as well'as, optionally, optical brighteners, antimicrobial active substances, souringand sequestering agents, perfumes and dyes, etc.
  • the powdery agents of the invention are present as powders, agglomerates or granulates.
  • a particle size of from 0.1 to 3 mm. is desirable, preferably at least 70% of the particles should be from 0.3 to 2 mm.
  • the term powdery is used here in its general meaning, as is it usually employed in connection with textile auxiliaries, so that particle sizes from a fine powder to coarse grains including granulates are included.
  • the agents of the invention are distinguished by a good dispersibility in cold water.
  • fabrics hardened by washing, particularly cotton terry cloth become soft and nappy.
  • Particularly advantageous, in comparison to known cationic softeners, is the pratically insignificant effect on the absorptivity of these fabrics.
  • the softening rinsing agents for washed textiles of the invention render, therefore, the fabric hardened by washing, particularly cotton terry cloth, again agreeably soft and nappy.
  • Such treated fabrics possess, in comparison to the untreated washing goods, only a slightly diminished absorptivity and in comparison to the washing goods treated with known cationic softeners, a substantially improved absorptivity.
  • an undesirable static charging of the textiles, particularly those of synthetic fibers is largely prevented.
  • the powdery agents of the invention are utilized in such amounts that the concentration of the textile softener of Formula I is in the range of from 0.1 to 2.0, preferably from 0.2 to 1.0 gm./l. of the aqueous treatment liquor.
  • composition of the powdery softening rinsing agents for laundry of the invention lies generally in the range of the following formulation based on the anhydrous substances:
  • the active softening ingredients of Formula I used according to the invention, can be prepared in a known, not claimed herein, manner.
  • the compounds of Formula I may be obtained by the reaction of the alkali salts of the unsaturated carboxylic acids with 3-chloro-2-hydroxypropyltrialkyl-ammoniurn halide or by the reaction of the unsaturated carboxylic acid with glycidyl-trialkyl-ammonium halide.
  • the compounds may be obtained from the unsaturated carboxylic acid, an epihalohydrin, for instance, epichlorohydrin, and a tertiary amine by reaction in an inert solvent.
  • the particularly preferred compounds of the Formula I are the esters of acrylic, methacrylic and crotonic acids, 3-butene carboxylic acid and 3-methyl-3-butene carboxylic acid, as well as of maleic, fumaric, itaconic, mesaconic, methylenemalonic, citraconic, muconic acids, etc.
  • the compounds of the Formula I are obtained, as already mentioned, in the preparation generally as halides, particularly as chlorides and bromides.
  • the compounds of the Formula I are also incorporated into the agents of the invention as halides.
  • at least part of the halide anions may be replaced by other acid radicals which are generally admixed into the preparations of the invention as alkali metal salts and present in this form, conventional ingredients of the softening rinsing agents for washed textiles.
  • the carboxylic esters of the Formula I are mostly present as oily, pasty or waxy substances. Their consistency depends widely upon the length and degree of saturation of the radicals R and R ;,also whether the radicals R and R possess a homogenous chain length or if they are present as technical mixtures of homologs.
  • These solid to oily active substances are readily converted to powdery products when they are suitably admixed with the named solid carriers.
  • the invention relates further to processes for the preparation of powdery softening rinsing agents for laundry of the above given composition.
  • the preparations of the invention are obtained by spraying the active substance of the Formula I in the temperature range of from 20 C. to 80 C. onto a moving bed of the solid carriers together with the nonionic dispersing agents and, optionally, other customary ingredients, particularly optical brighteners, in a liquid mixture with water and/or volatile organic solvents from the group of methanol, ethanol, isopropanol, acetone, methylene chloride, chloroform.
  • carriers are used with a surface as large as possible and a low bulk weight, for instance a bulk weight of from 100 to 700 gm./l. Products of such bulk weight are obtained, for instance, by calcination of crystal-water containing inorgnaic salts, particularly of sodium sulfate.
  • Another preparation process for the agents of the invention is characterized in that an aqueous mixture of the ingredients, which are preferably present in a concentration of from 15%. to 35% by weight, is heat-dried at temperatures above 100 C., preferably in the range of from 105 to 125 C.
  • the heat-drying is carried out by pouring of the aqueous mixture in a thin layer onto hot surfaces.
  • Another preferred variant is characterized in that the heat-drying is effected by spraying of the aqueous charge into a hot gas stream.
  • the powder properties of the process products may be improved by incorporation of slight amounts of substances with a large surface, such as microcrystalline silicic acid, magnesium silicate, etc.
  • preparations of the invention produced by the named processes are distinguished by good pourability and goor storability, dustlessness and by quick dispersibility in cold water.
  • preparations of the invention contain temperatures sensitive or volatile ingredients, such as the below-named antimicrobial or perfumes, they are added to the finished powder.
  • nonionic surfaceactive agents are particularly suited, here designated in the following as nonionics. These are products which owe their hydrophilic properties to the presence of polyether chains, amineoxide, 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 10 to 20 and particularly 12 to 18 carbon atoms and at least one nonionic water-solubilizing group.
  • the preferably saturated hydrophobic radical is mostly of an aliphatic, optionally also alicyclic nature.
  • connecting member for instance, benzene rings, carboxylic acid ester or carbonamide groups, etherlike 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.
  • nonionics further belong the products, known under the trade name Pluronics or Tetronics. They are obtained from water-insoluble polyoxypropylene glycols of from water-insoluble propoxylated lower aliphatic alcohols, containing 1 to 8, preferably 3 to 6 carbon atoms, or from water-insoluble propoxylated alkylene diamines. These water-insoluble (that is hydrophobic) propylene oxide derivatives are transformed by ethoxylation to give water-solubility and come under the named nonionics. Finally, as nonionics, Ucon-Fluid which are partly still watersoluble reaction products of the above-named aliphatic alcohols with propylene oxide, are useable.
  • fatty acid or sulfonic acid alkylolamides' which are derived, for instance, from mono or diethanolamine, from dihydroxypropylamine or other polyhydroxyalkylamines, for instance the glycamines are in the class of useable nonionics.
  • the surface-active amine oxides belong, for instance, the products derived' from higher tertiary amines containing one hydrophobic alkyl aradical and two shorter alkyl and/or alkylol radicals with up to 4 carbon atoms.
  • nonionic dispersing agents optionally suitable are also non-surface-active, water-soluble or water-emulsifiable or dispersible compounds, such as partial fatty acid glycerides as well as such compounds which contain no hydrophobic radicals in the sense of the above-described nonionic surface-active agents, such as polyethylene glycols, ethylene oxide adducts of glycerine and other polyalcohols, etc.
  • Inorganic and non-surface-active organic acids innocuous to the fibers to be treated, with 1 to 8 carbon atoms are suitable as souring and sequestering agents, such as amidosulfonic acid, urea compounds of orthophosphoric acid, boric acid, oxalic acid, lactic acid, glycolic acid, citrica 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.
  • amidosulfonic acid such as amidosulfonic acid, urea compounds of orthophosphoric acid, boric acid, oxalic acid, lactic acid, glycolic acid, citrica acid, tartaric acid, benzoic acid, phthalic acid, gluconic acid, acetic acid and propionic acid as Well as benzene, toluene or
  • Mono or polycarboxylic acids or hydroxycarboxylic acids or their water-soluble salts from the group of the oxalic acid, lactic acid, glycolic acid, citric acid, tartaric acid, luconic acid, malonic acid are in the class of sequestering agents.
  • Anti-mirobial 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, usuable 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. Examples for such anti-microbial quaternary ammonium compounds are the following:
  • dimethyl-benzyl-dodecyl-ammonium chloride dimethyl-benzyl-tetradecyl-ammonium chloride, dimethyl- (ethylbenzyl)-dodecyl-ammonium chloride, dimethyl-benzyl-decyl-ammonium bromide, diethyl-benzyl-dodecyl-ammonium chloride, diethyl-benzyl-octyl-ammonium chloride, dibutyl-allyl-, methyl-ethyl-benzyl-, ethyl-cyclohexyl-allyland ethyl-crotyl-diethylaminoethyl-', dodecyl-ammonium chlorides.
  • Other usable antimicrobial active substances are the lower alcohols or diols, substituted both by bromine and nitro groups, with 3 to carbon atoms, such as the compounds 2-bromo-2-nitro-propanediol-1,3, l-bromo 1 nitro-3,3,3-trichloropropanol-2, 2-bromo 2 nitro-butanol-l.
  • the usable brighteners are mostly, if not exclusively, derivatives of aminostilbene-sulfonic acid or diaminostilbene-sulfonic acid, diarylpyrazolines, carbostyryls, 1,2-di- (2-benzoxazolyl)- or 1,2-di-(Z-benzimidazolyl)-ethylenes, benzoxazolyl-thiophens, and of the coumarins.
  • Examples for brighteners from the class of the derivatives of the diaminostilbene sulfonic acid are compounds according to Formula II:
  • 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 1 to 4, and especially 2 to 4 carbon atoms, and in the heterocyclic ring systems, fiveor six-membered 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 -NH-C H and R may represent the following residues, are at present on the market.
  • Some of these brighteners are to be regarded as transitional types to the cotton brighteners as regards their aflinity for the fiber, for example the brightener in which R equals -NH--C H
  • the compound 4,4-bis-(4- phenyl-l,2,3-triazolyl-2-)-stilbenedisulfonic acid-2,2 also belongs to the cotton brighteners of the diaminostilbenesulfonic acid type.
  • Diarylpyrazolines of Formulas III and IV belong to the polyamide brighteners
  • R and R represent hydrogen atoms, or
  • 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, carboxyl, carboxylic acid ester, sulfonic acid, sulfonamide and sulfone group or halogen atoms.
  • 9-cyano-anthracene is also on the market as a polyamide brightener.
  • polyamide brighteners for example, 4-methyl 7 dimethylaminoor 4-methyl-7-diethylamino-coumarin.
  • polyamide brighteners are the compounds l-(benzimidazolyl- )-2-(1-hydroxyethylbenzimidazolyl-2)-ethylene and 1-ethyl-3-phenyl-7-diethylamino-carbostyryl.
  • Suitable brighteners for polyester and polyamide fibers are the compounds 2,5-di-(benzox azolyl-2)-thiophene and 1,2-di-(5'-methyl-benzoxazolyl- 2')-ethylenc.
  • EXAMPLE 1 20.0% by weight of the acrylic acid esters of [2-hydr0xy- 3-(N,N-dihexadecyl N methylammonium)-propyl] chloride,
  • glycolic acid 2.0% by weight of glycolic acid 3.0% by weight of the adduct of nonylphenol with 9 to 10 mols of ethylene oxide 15.0% by weight of sodium sulfate (anhydrous),
  • the softening rinsing agent for laundry was prepared as follows: The textile softener and the nonionic dispersing agent were melted to a homogenous mixture at 50 C. to 60 C. Simultaneously, the organic acid and the carriers were dissolved in water, preheated to 50 C., and the above-named melt was stirred into this solution. The amounts were utilized so that 1 kg. of all the ingredients of the softening rinsing agent of above composition was allotted to 5 liters of water. The dispersion thus obtained was atomized in a spray tower at C. A white, finegrained and good pourable powder resulted. To the finished preparation perfumes and anti-microbial active substances may be added.
  • the textile softener the acrylic acid ester of [2-hydroxy 3 (N,N-di-hexadecyl-N-methylammonium)-pr0- pyl] chloride, used according to Example 1, can be prepared by the following procedure, according to US. Pat. 3,397,227.
  • EXAMPLE 2 20.0% by weight of themethacrylic acid ester of [2-hydroxy-3-(N,N-ditetradecyl-N-methylammonium) propyl] chloride,
  • glycolic acid 100% 3.0% by weight of the adduct of nonylphenol with 9 to 10 mols of ethylene oxide
  • the softening rinsing agent for laundry according to Example 2 was prepared as follows:
  • EXAMPLE 3 18.2% by weight of the methacrylic acid ester of [2-hydroxy-3-(N,N-ditetradecyl N methylammonium-propyl] chloride,
  • glycolic acid 100% 2.7% by weight of the adduct of nonylpehnol with 9 to 10 mols of ethylene oxide
  • the softening rinsing agent for laundry was prepared as follows:
  • the textile softener and the non-ionic dispersing agent were melted together at 50 C. to 60 C. to a homogenous mixture and simultaneously glycolic acid, sodium sulfate and urea were mixed at 50 C. with a 26-fold amount of water.
  • the above named melt was stirred into this mixture and the slurry, thus obtained, was brought onto a roller-drier, whose rolls had a temperature of 140 C.
  • the scales were converted into a powder by grinding.
  • the other specified preparations, according to the invention can also be prepared by this method.
  • EXAMPLE 4 20.0% by weight of the maleic acid bis-ester of [Z-hydroxy-3-(N,N-didodecyl N methylammonium)-propyl] chloride,
  • glycolic acid 100% 3.0% by weight of the adduct of cetyl-oleyl alcohol with 10 mols of ethylene oxide
  • EXAMPLE 20 0% by weight of the methacrylic acid ester of [2-hydroy-3-(N,N-ditetradecyl N methylammonium)-propyl] chloride,
  • glycolic acid 100% 2.9% by weight of the adduct of a fatty alcohol (C C;,;) with 4 mols of ethylene oxide
  • Examples 4 and 5 can be prepared by any of the methods specified in Examples 1 to 3.
  • the powdery softening rinsing agents for laundry of the invention are distinguished by a quick distribution and dispersion in cold water, so that theeffect of the textile softener at its use in the last rinsing cycle of a washing machine is complete.
  • the treatment with the preparations of the invention leads already at an applicationconcentration of 0.5 gm. of the textile softener per liter of rinsing liquor to a full and soft hand of hardened fabric.
  • the soft-rinsed fabrics possess also a good absorptivity.
  • Powdery softening rinsing agent compositions for washed textiles consisting essentially of (1) from 1% to 50% by weight of an unsaturated carboxylic acid ester of the formula wherein R and R are selected from the group consisting of alkyl and alkenyl having from 10 to 24 carbon atoms, R is alkyl having 1 to 4 carbon atoms, A is selected from the group consisting of alkenyl and alkenylene having from 2 to 5 carbon atoms, X is a halide anion and n is an integer of 1 to 2, (2) from 0.2% to 10% by weight of at least one non-ionic surface-active dispersing agent selected from the group consisting of a water-soluble dispersing agent and a water-dispersible dispersing agent, and (3) the remainder up to by weight of at least one solid diluent carrier compatible with rinsing agents for washed laundry selected from the group consisting of easily water-soluble compounds and easily, in-water-dispersible compounds, where said unsaturated carboxy
  • powdery softening rinsing'agent compositions of claim 1 wherein said solid diluent carrier compatible with rinsing agents for washed laundry is an inert easily-watersoluble or easily-water dispersible solid carrier selected from the group consisting of urea, acetamide, biuret, sodium sulfate and solid polyethylene glycols.
  • component (1) is present in an amount of from 5% to 25% by weight, and component (2) is present in an amount of from 1.0% to 6.0% by weight.

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3896034A (en) * 1970-10-20 1975-07-22 Henkel & Cie Gmbh Softening agent compositions
US3984335A (en) * 1975-01-16 1976-10-05 Basf Wyandotte Corporation Compositions for souring and softening laundered textile materials and stock solutions prepared therefrom
US4060505A (en) * 1975-01-16 1977-11-29 Basf Wyandotte Corporation Compositions for souring and softening laundered textile materials and stock solutions prepared therefrom
US4427558A (en) 1981-05-08 1984-01-24 Lever Brothers Company Fabric conditioning materials
CN110184813A (zh) * 2019-06-11 2019-08-30 新昌县高纤纺织有限公司 环保型羊毛蛋白纤维混纺纱

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CS208979B1 (en) * 1979-06-20 1981-10-30 Jan Novak Textile brightening agent with antistatic effect having positive dermatological affects upon skin
FR2505357B1 (fr) * 1981-05-07 1984-10-05 Reckitt & Colmann Sa Compositions de rincage pour le linge
DE3274747D1 (en) * 1982-11-05 1987-01-29 Reckitt & Colmann Sa Rinse compositions for laundry
US4840738A (en) * 1988-02-25 1989-06-20 The Procter & Gamble Company Stable biodegradable fabric softening compositions containing 2-hydroxypropyl monoester quaternized ammonium salts

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3329706A (en) * 1964-03-23 1967-07-04 Shell Oil Co 2-hydroxy-3-alkenoyloxypropyltrialkylammonium halides
DE1617130A1 (de) * 1967-05-09 1971-03-04 Henkel & Cie Gmbh Mittel zum Nachbehandeln gewaschener Waesche

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3896034A (en) * 1970-10-20 1975-07-22 Henkel & Cie Gmbh Softening agent compositions
US3984335A (en) * 1975-01-16 1976-10-05 Basf Wyandotte Corporation Compositions for souring and softening laundered textile materials and stock solutions prepared therefrom
US4060505A (en) * 1975-01-16 1977-11-29 Basf Wyandotte Corporation Compositions for souring and softening laundered textile materials and stock solutions prepared therefrom
US4427558A (en) 1981-05-08 1984-01-24 Lever Brothers Company Fabric conditioning materials
CN110184813A (zh) * 2019-06-11 2019-08-30 新昌县高纤纺织有限公司 环保型羊毛蛋白纤维混纺纱
CN110184813B (zh) * 2019-06-11 2021-10-22 上海荟姿新材料科技有限公司 环保型羊毛蛋白纤维混纺纱

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BE781124A (fr) 1972-09-25
FR2130652A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1972-11-03
FR2130652B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1974-10-18
ZA721991B (en) 1972-12-27
IT950442B (it) 1973-06-20
BR7103179D0 (pt) 1973-04-10
AT320830B (de) 1975-02-25
NL7105926A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1972-09-26
DE2114129A1 (de) 1972-09-28

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