US3625891A - Wash cycle fabric softeners and method of preparing and using same - Google Patents

Wash cycle fabric softeners and method of preparing and using same Download PDF

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Publication number
US3625891A
US3625891A US722171A US3625891DA US3625891A US 3625891 A US3625891 A US 3625891A US 722171 A US722171 A US 722171A US 3625891D A US3625891D A US 3625891DA US 3625891 A US3625891 A US 3625891A
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fabric
percent
composition
quaternary ammonium
softener
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US722171A
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Milton M Waldman
Andrea E Mariahazy
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Armour Industrial Chemical Co
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Armour Industrial Chemical Co
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    • 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

Definitions

  • This invention relates generally to laundry products and more particularly to compositions comprising particular proportions of certain quaternary ammonium compounds, which have utility as cationic fabric softeners in industrial and household applications. This invention is also concerned with methods of preparing such compositions and of softening fabrics wherein compositions of this invention are applied to thefabrics.
  • cationic fabric softeners usually comprising the di-long chain alkyl quaternary ammonium compounds such as dimethyl dihydrogenated tallow ammonium chloride
  • care must be taken to avoid contact of the softener with anionic soaps and anionic detergents and builders generally used in washing fabric.
  • Cationic softeners are generally not compatible with such materials and may be precipitated or rendered inactive by contact with them. It has been estimated that over 50 percent of the potential consumer fabric softener market is thereby lost through the resulting necessity of adding the softener to the rinse cycle instead of to the wash cycle along with the cleansing agents; e.g.
  • a second problem encountered in the use of known cationic fabric softeners is that the fabric may tend to resist the absorption of water after repeated applications (even though there are several intervening washings of the fabric), and the rewet" property of the fabric can be drastically hindered. This problem is important where water absorption is desired, such as with diapers.
  • a second material is added to an effective cationic softener, such as to the dimethyl dihydrogenated tallow ammonium chloride, it is generally found that the second material does not aid the quaternary in its function as a softening agent but in effect constitutes waste material so far as softening is concerned.
  • a fabric softening composition comprising about I to 20 percent by weight of fabric-softening agents which comprise the combination, by weight based on the total weight of fabric softening agents present in the composition, of: (A) about 25 percent diaralkyl quaternary ammonium compounds, (B) from I to 75 percent mixed di-long chain alkyl quaternary ammonium compounds and (C) from 74 to 1 percent dialkyl quaternary ammonium compounds.
  • These combinations of quaternaries can be readily dispersed in warm water. They fonn stable dispersions, which show little or no tendency to precipitate, in aqueous solutions of anionic and/or nonionic detergents and the like materials. Furthen'nore, when fabrics are laundered with the compositions and a detersive amount of detergent, they are effectively not only washed by the detergent, but also softened by the composition.
  • a further illustrative, and even more specific, embodiment of the fabric-softening agents of our compositions is the combination comprising by weight about 25 percent dimethyl diphenylstearyl ammonium chloride; from I to 74 percent dimethyl mixed-dialkyl [hydrogenated tallow:secondary-alkyl (C -Cg] ammonium chloride; and from 74 to 1 percent dimethyl dihydrogenated tallow ammonium chloride.
  • the quaternaries may be combined by admixing the individually formed quaternaries, or by forming a blend of the quaternaries formed in situ by quaternizing the appropriate proportions of precursor chemicals.
  • a highly preferred specific illustrative embodiment of the fabric softening agent comprises, by weight, about 25 percent dimethyl diphenylstearyl ammonium chloride, 30-45 percent and particularly toward about 35 percent dimethyl mixed dialkyl [hydrogenated tallow: secondary-alkyl (C -Cm] ammonium chloride, and 45-30 percent and particularly toward about 35 percent dimethyl dihydrogenated tallow ammonium chloride.
  • the softening compositions of this invention represent a refined balance of quaternaries combined in specific manners in order to produce a composition giving optimum results.
  • R is selected from the group consisting of phenyl, naphtyl, tolyl, anisyl, and xylyl;
  • R is selected from the group consisting of lower alkyl radicals containing from one to three carbon atoms and -(CI-I,CH,O).H where n is an integer from l to l0;
  • A is an anion such as a halogen, a nitrate, a sulfate such as methyl sulfate or ethyl sulfate, a phosphate, an acetate, and the like;
  • x and y are each integers from 0 to 19 whose sum is an integer ranging from 5 to 19.
  • R, and R are each different or asymmetrical long chain alkyl radicals containing from eight to 24 carbon atoms; and R; and A are as defined hereinabove.
  • Suitable quaternaries of this class are described in copending application filed Feb. 29, I968, Ser. No. 709,2 [0 by Charles S. Wilhelmy et al., and titled QUATERNARY AMMONIUM SALTS OF MIXED AMINES, METHOD OF THEIR PREPARATION, AND THEIR USE (Case 4926/5042).
  • the Canadian counterpart of the preceding application has issued in Canada as Canadian Patent 866,208.
  • Desirable quaternaries of this class for use in the invention include those where R, is selected from the group consisting of methyl and -(CH,CH,O),,H where n is an integer from 1 to 5, and A is chloride.
  • R, and R may be straight or branch chain alkyl such as n-alkyl or secondary-alkyl, saturated or unsaturated alkyl and may be unsubstituted or substituted with relatively unreactive aryl groups such as phenyl, naphthyl, tolyl, anisyl, and the like.
  • Examples of preferred quaternaries of this class include dimethyl hydrogenated tallow:(C ,-C,.)-secondary-alkyl ammonium chloride, dimethyl hydrogenated tallowzcoco ammonium chloride, methyl beta-hydroxyethoxyethyl hydrogenated tallow:(C -C)-secondary-alkyl ammonium chloride, bis-(2- hydroxyethyl) hydrogenated tallow:(C,,-C,,)-secondary-alkyl ammonium chloride, and dimethyl phenylstearylzhydrogenated tallow ammonium chloride.
  • Dialkyl Quaternary Ammonium compounds of this type that are useful in the present invention may be represented by the formuwherein R and A are as defined hereinabove; and each R, represents a long chain hydrocarbon derived from a fatty acid, usually having from eight to 24 carbon atoms and preferably l6 to 22 carbon atoms. Any known type of rinse added cationic softener such as quatemized imidazolines and/or amido-amine may be used to comprise component (C).
  • 75 percent active softening agents of this invention as fabric softeners in aqueous solutions, from 0.01 to 0.5 percent by weight, and preferably about 0.2 percent, is desirable for wash water addition. They may also be added to rinse water, and here 0.0] to 0.5 percent by weight may be used with about 0.] percent being especially desirable.
  • the percent by weight of softening agent is based on the weight of fabric to be treated, and thus a concentration of about0.2 percent is about 5-7 grams per 6 to 7 pounds offabric to be treated.
  • aqueous concentration of aboutl to percent by weight of the softener is generally utilized. Similar formulations for the composition of this invention may also be utilized for retail sale.
  • composition of the invention may be combined with a wide range of detergent concentration, depending generally upon the particular detergents used and the degree of cleansing effect desired. Conventionally used detergents and concentrations thereof, e.g., as recommended by detergent manufactures, may be employed. From 0.1-0.5 percent in solution is preferred.
  • Our cationic softener composition is compatible with conventional soaps, synthetic detergents of the anionic and nonionic types, and mixtures thereof.
  • the compatibility is due to the proportioning of the three different classes of quaternaries, particularly with regard to having about percent diaralkyl quaternary present. It appears that the arylated constituents thereof provide detergent compatibility while the branch chain constituent gives linking compatibility between the two other quaternaries which provide the major softening and compatibility effects. About 25 percent proportion of diaralkyl quaternary is desirable to achieve these effects.
  • the suitable conventional soaps may be described as the water-soluble, ammonium or alkali metal or organic base salts of various fatty acids having about from 12 to l8 carbon atoms.
  • Suitable anionic synthetics may be described as those detergents having pronounced cleansing power and including in their molecular structure an alkyl radical containing from six to l8 carbon atoms and a sulfonic acid or sulfuric acid ester radical.
  • Organic base, ammonium, sodium, or potassium salts of the anionic detergents may be used.
  • alkylaryl sulfonates such as sodium or potassium dodecylbenzene sulfonate, sodium or potassium octylnaphthalene sulfonate
  • alkyl sulfonates such as sodium or potassium salts of dodecyl, hexadecyl and octadecyl sulfates
  • the sulfonated fatty acid amines such as sodium or potassium salts of the oleic acid amide of methyltaurine
  • the sulfonated monoglycerides such as the monococonut fatty acid ester of 1,2-hydroxypropane-3-sodium sulfonate.
  • linear alkyl groups are especially desirable because of their biodegradable features; and preferably they contain l2 to 14 carbon atoms in their alkyl group, such as dodecylbenzene sulfonate or tridecylbenzene sulfonate.
  • Useful nonionic detergents may be described as those detergents which do not ionize in solution, but owe their water solubility to nonionizing polar groups such as hydroxyl or ether linkages.
  • the main types of detergents falling within this category are the polyoxyethylene ethers of the higher fatty alcohols and alkyl phenols; the polyethylene glycols of fatty acids; fatty alkanolamide condensation products; Fatty acid ethylene oxide condensation products; condensation products of ethylene oxide and a fatty acid ether of a polyhydric alcohol or sugar; and the detergents prepared by heating together a higher fatty acid with an alkanolamine, e.g., mono-, di-, and triethanolamine; and the like.
  • an alkanolamine e.g., mono-, di-, and triethanolamine
  • the softener composition may contain, in addition, any of the usual optional ingredients such as dyes, perfumes, brighteners, and other optional additives. Any normally used laundry aids such as bleach, chlorine, oxygen, and water softeners may also be employed. No additional rewet agent is necessary, but may be employed.
  • a typical formulation of a softener of the invention, which may be added along with a heavy duty detergent to the wash cycle, is:
  • This fonnulation may preferably be added at a concentration of 0.2 percent by weight on the basis of the weight of the fabric, or about 5-7 grams of active material for an average 6-7 pound load of fabric.
  • the formulation may be prepared by heating the softening agent to about F. until it becomes a clear liquid, heating dilution water to about 140 F. and adding to the water first one-half of the salt and then the softening agent, then mixing to disperse while adding sufficient salt to thin to desired viscosity, add acid and color, and finally cool the composition and add perfume.
  • Concentrations of the softener combination of the invention were 0.1 percent by weight basis the fabric for rinse cycle addition, and 0.2 percent by weight basis the fabric for wash cycle addition. The concentration of the particular detergent used in the wash cycle was 0.2 percent.
  • Softening was determined by panel preference; rewet by wicking test procedure; detergency by reflectometer readings of soiled cloth; and whiteness retention and soil removal were determined by test cloths in the stan- '0.
  • I Q- added on weight basis fabric Table ll sets forth the softening pieferences of other combinations of the quaternary ammonium compounds of the invention.
  • An Ethoxylated Softener of the invention 25% his-(Z-hydroxyethyl) phenylstearyl ammonium chloride 50% his-(Z-hydroxyethyl) mixed hydrogenated tallow: (C -C sec-alkyl ammonium chloride 30.0% 25% dimethyl di hydrogenated tallow ammonium chloride untreated control 32.1%
  • Soil removal and whiteness retention were determined on standard soil test cloths included in family laundry bundles. These evaluations were augmented by observations and comments from consumer test panel evaluations as follows: the softener was added to the water containing detergent prior to adding the clothes or after the agitation had begun. The amount of detergent used was detennined by manufactures direction: suds level for high-sudsing detergents, and empirically for the low sudsers. In these evaluations, detergency was comparable whether the known softener dimethyl dihydrogenated tallow ammonium chloride was used in the rinse cycle or whether the softener combination of the invention was used in the wash cycle. Detergency reduction by the combination of the invention was within less than 10 percent of that by most rinse-added softeners. The whiteness retention was not affected by either rinse or wash-added softeners when the detergent was the built alkyl aryl sulfonate plus alkyl sulfate. No important differences were obtained with the other detergent systems.
  • the softener combination of the invention was evaluated for sanitizing properties.
  • a quantitative evaluation for antibacterial properties of treated cloths was run according to AATCC Method lOO-l96 l-T, using Staphylococcus au reus FDA Strain No. 209.
  • Table III sets forth the percent reduction of incubated bacterial population by the sanitizing action of the softeners under this method and also in cold water washing with the built alkyl aryl sulfonate plus sodium soap detergent.
  • a diaralkyl quaternary ammonium compound having the formula wherein R is selected from the group consisting of phenyl, naphthyl, tolyl, anisyl and xylyl, R is selected from the group consisting of alkyl radicals having one to three carbon atoms and (CH,CH,O),,H wherein n is an integer of l to 10,1: and y are integers having a sum of to l9. and A is an anion;
  • R, and R are difierent and each are mixtures of radicals selected from the group consisting of n-alkyl and secondary-alkyl radicals having eight to 24 carbon atoms.
  • R, and A are as defined above;
  • a dialkyl quaternary ammonium compound having the formula wherein R is an alkyl group having eight to 24 carbon atoms, R; and A are as defined above.
  • composition of claim 1 wherein said mixed-dialkyl quaternary ammonium compound and said dialkyl quaternary ammonium compound are each present in about 30 to 45 weight percent.
  • composition of claim 3 in which said diaralkyl quaternary ammonium compound is dimethyl diphenyl stearyl ammonium chloride.
  • a fabric softening composition compatible with detergents in the wash waters of fabric during laundering consisting essentially of about 1 to 20 wt. percent of a fabric softener concentrate in aqueous solution, said fabric softener concentrate consisting essentially of:
  • a diaralkyl quaternary ammonium compound having the formula consisting of alkyl radicals having one to three carbon atoms and (CH,CH,O),H wherein n is an integer of l to H), x and y are integers having a sum of5 to 19, and A is an anion;
  • Rr-N- a mixed-dialkyl quaternary ammonium compound having the formula Rr-N- wherein R, and R, are difierent and each are mixtures of radicals selected from the group consisting of n-alkyl and secondary-alkyl radicals having eight to 24 carbon atoms, R, and A are as defined above;
  • a dialkyl quaternary y I ammonium compound having the formula wherein R is a alkyl group having eight to 24 carbon atoms.
  • R, and A are as defined above.
  • a diaralkyl quaternary ammonium compound having the formula wherein R is selected from the group consisting of phenyl, naphthyl, tolyl, anisyl and xylyl, R, is selected from the group consisting of alkyl radicals having one to three carbon atoms and (CH,CH,O),.H wherein n is an integer of l to 10.x and y are integers having a sum of 5 to 19. and A is an anion;
  • a mixed-dialkyl quaternary ammonium compound having the formula IAl' wherein R, and R, are different and each are mixtures of radicals selected from the group consisting of n-alkyl and secondary-alkyl radicals having eight to 24 carbon atoms, R; and A are as defined above; and
  • ammonium compound having the formula R, and A are as defined above.

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  • Textile Engineering (AREA)
  • Detergent Compositions (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US722171A 1968-04-18 1968-04-18 Wash cycle fabric softeners and method of preparing and using same Expired - Lifetime US3625891A (en)

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JP (1) JPS4944040B1 (enrdf_load_stackoverflow)
DE (1) DE1919622A1 (enrdf_load_stackoverflow)
FR (1) FR2006470A1 (enrdf_load_stackoverflow)
GB (1) GB1257386A (enrdf_load_stackoverflow)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3979307A (en) * 1972-09-20 1976-09-07 Texaco Inc. Fabric softener composition
US4214998A (en) * 1978-02-24 1980-07-29 Imperial Chemical Industries Limited Quaternary ammonium compounds useful as fabric softening agents
US4392965A (en) * 1981-11-12 1983-07-12 Woodward Fred E Laundry softener antistatic composition
US4559151A (en) * 1984-05-07 1985-12-17 Sterling Drug Inc. Antistatic fabric conditioner compositions and method
US4842760A (en) * 1987-05-26 1989-06-27 Kao Corporation Soft finishing agent

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1596791A (en) * 1977-02-15 1981-08-26 Unilever Ltd Deodorant detergent composition
US4873346A (en) * 1985-09-20 1989-10-10 The Upjohn Company Substituted benzothiazoles, benzimidazoles, and benzoxazoles

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3325404A (en) * 1963-09-19 1967-06-13 Millmaster Onyx Corp Composition for simultaneously laundering and softening fabrics
US3349033A (en) * 1964-08-26 1967-10-24 Millmaster Onyx Corp Stable microbiologically active laundry softener
US3366673A (en) * 1964-04-03 1968-01-30 Millmaster Onyx Corp Microbiologically active quaternary ammonium compounds
US3444200A (en) * 1965-10-21 1969-05-13 Armour Ind Chem Co Aryl-alkyl quaternary ammonium compounds
US3505221A (en) * 1966-07-20 1970-04-07 Armour Ind Chem Co Fabric softener

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3325404A (en) * 1963-09-19 1967-06-13 Millmaster Onyx Corp Composition for simultaneously laundering and softening fabrics
US3366673A (en) * 1964-04-03 1968-01-30 Millmaster Onyx Corp Microbiologically active quaternary ammonium compounds
US3349033A (en) * 1964-08-26 1967-10-24 Millmaster Onyx Corp Stable microbiologically active laundry softener
US3444200A (en) * 1965-10-21 1969-05-13 Armour Ind Chem Co Aryl-alkyl quaternary ammonium compounds
US3505221A (en) * 1966-07-20 1970-04-07 Armour Ind Chem Co Fabric softener

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3979307A (en) * 1972-09-20 1976-09-07 Texaco Inc. Fabric softener composition
US4214998A (en) * 1978-02-24 1980-07-29 Imperial Chemical Industries Limited Quaternary ammonium compounds useful as fabric softening agents
US4392965A (en) * 1981-11-12 1983-07-12 Woodward Fred E Laundry softener antistatic composition
US4559151A (en) * 1984-05-07 1985-12-17 Sterling Drug Inc. Antistatic fabric conditioner compositions and method
US4842760A (en) * 1987-05-26 1989-06-27 Kao Corporation Soft finishing agent

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JPS4944040B1 (enrdf_load_stackoverflow) 1974-11-26
FR2006470A1 (enrdf_load_stackoverflow) 1969-12-26
GB1257386A (enrdf_load_stackoverflow) 1971-12-15
DE1919622A1 (de) 1969-11-13

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