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US3349033A - Stable microbiologically active laundry softener - Google Patents

Stable microbiologically active laundry softener Download PDF

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Publication number
US3349033A
US3349033A US39230764A US3349033A US 3349033 A US3349033 A US 3349033A US 39230764 A US39230764 A US 39230764A US 3349033 A US3349033 A US 3349033A
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Prior art keywords
ammonium
softener
alkyl
dimethyl
chloride
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Zuccarelli Vincent
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Millmaster Onyx Corp
Millmaster Onix Group Inc
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Millmaster Onyx Corp
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    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS, OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M16/00Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL AND VEGETABLE OILS, FATS, FATTY SUBSTANCES AND WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/62Quaternary ammonium compounds
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL AND VEGETABLE OILS, FATS, FATTY SUBSTANCES AND WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005Other compounding ingredients characterised by their effect
    • C11D3/001Softening compositions
    • C11D3/0015Softening compositions liquid
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS, OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating 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
    • D06M13/372Treating 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 containing etherified or esterified hydroxy groups Polyethers of low molecular weight
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS, OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating 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
    • D06M13/46Compounds containing quaternary nitrogen atoms
    • D06M13/463Compounds containing quaternary nitrogen atoms derived from monoamines

Description

United States Patent 3,349,033 TABLE MICROBIOLOGICALLY ACTIVE LAUNDRY SOFTENER Vincent Zuccarelli, Staten Island, N.Y., assignor, by mesne assignments, to Millmaster Onyx Corporation, New York, N.Y., a corporation of New York No Drawing. Filed Aug. 26, 1964, Ser. No. 392,307 Claims. (Cl. 2528.75)

It is well known to the art to apply to laundered goods aquarternary ammonium salt as a cationic softener of the type:

wherein R and R represent alkyl radicals having to carbon atoms, R" is a methyl radical, R is a methyl, ethyl, an ethoxylated radical (CH CH O),,H where n is an integer of at least one, and X is a chlorine, bromine, sulfate, methosulfate, or ethosulfate, by dissolving such a softener in the final rinse water. Similar materials have also been used by textile mills as softeners applied in the final rinse. In the preceding formula, R and R represent an alkyl radical or mixture of alkyl radicals having from 10 to 20 carbon atoms usually derived from tallow. Quaternary ammonium compounds of this type are sold in substantial volume and are used in the application set forth above, more particularly in the last rinse in household laundering operations. They impart to the treated goods a pleasant, soft hand and have found much favor with housewives.

The preferred alkyl radical, R, in these compounds is usually a mixture containing about 60 to 80% of stearyl and about 20 to of cetyl radicals and is ordinarily derived from tallow, preferably by hydrogenation or by hydrogenation of its derivatives used as intermediates in the production of the quaternary ammonium compounds.

It has been found that mixtures of known fabric softeners of the type previously mentioned and known germicidal quaternary ammonium salts will not remain homogeneous for more than a few days or at most a few weeks even at ordinary temperatures. Such mixtures are quite unstable in hot weather, or when exposed to freezing. This is surprising, since it would have been expected that two quaternary ammonium salts, each of which contains at least one long carbon chain, would be compatible in a mixture because of their close structural relationship.

Di-(hydrogenated tallow) dimethyl ammonium methosulfate which is well known to the art makes an especially desirable fabric softener. However, in combination with a quaternary ammonium salt such as is effective as a fabric sanitizing agent, the stability of the mixture is poor; that is, on aging, heating or cooling, it separates into two phases.

I have found surprisingly that the addition of a small amount of an emulsifier, such as a long chain fatty alcohol, to the mixture of a quaternary ammonium germicide with a fabric softener, such as the di-(hydrogenated tallow) dimethyl ammonium methosulfate, causes the mixture to remain homogeneously emulsified over a period of at least eight months, during which time it was stored at a temperature of 40 C. or 104 F. for a period of four months. It also causes the mixture to remain stable after several successive cycles of freezing and thawing followed by a period of storage at ordinary temperature for prolonged observation.

The fatty alcohols used in this invention suitable as the emulsifier may contain from 10 to 18 carbons in the chain. Topped coconut fatty alcohols, such as Lorol 5 which is effective has an alkyl distribution of about 3% C10, C12, C14, C16 and C18. However, any aliphatic alcohol with a chain length of C to C may be used.

I may use in my composition any high-potency quaternary ammonium microbiologi-cally active compounds having a phenol coefiicient of at least 200 as determined by the standard method given in the Official Methods of the Association of Agricultural Chemists, ninth edition, 1960. Typical examples of these quaternary ammonium compounds are alkyl dimethyl benzyl ammonium chloride in which the alkyl group may have from 8 to 22 carbon atoms, alkyl dimethyl substituted benzyl ammonium chlorides, in which the alkyl radical contains from 8 to 22 carbon atoms and in which the benzyl radical is substituted with one or more side chains containing from 1 to 4 carbon atoms such, for exai ple, as methyl, dimethyl, trimethyl, tetramethyl, ethyl, diethyl, isopropyl and tertiary butyl or with one, two, or more, halogen atoms such as chlorine and bromine, alkyl dimethyl menaphthyl ammonium chloride and alkyl dimethyl tetrahydromenaphthyl ammonium chloride in which the alkyl radical contains from 8 to 22 carbon atoms, alkyl benzyl trimethyl ammonium chloride in which the alkyl radical contains from 8 to 22 carbon atoms and in which the aromatic nucleus of the benzyl radical may, if desired, be substituted by one or more methyl or other lower alkyl groups, alkyl phenoxy ethoxy ethyl dimethyl benzyl ammonium chloride in which the alkyl radical may be isooctyl or nonyl, and mixtures of the aforesaid quaternary ammonium compounds.

The following illustrative high-potency quaternary ammonium germicides are useful in my laundry softener compositions: dodecyl trimethyl ammonium chloride, cetyl trimethyl ammonium chloride, p-diisobutyl phenoxy ethoxy ethyl dimethyl benzyl ammonium chloride, dodecyl benzyl trimethyl ammonium chloride. Also any highpotency quaternary ammonium germicide of the alkyl dimethyl benzyl ammonium chloride compounds may be used, such as those used in the following examples sold by Onyx Chemical Corporation under the designation consisting of a mixture of benzalkonium salts of equal parts of alkyl dimethyl benzyl ammonium chloride (in which the alkyl distribution is 60% C 30% C 5% C 5% C and alkyl dimethyl ethylbenzyl ammonium chloride (in which the alkyl distribution is C12, C14, C16, C13). The following are the advantages of such mixture: (a) a high phenol coefficient; namely, 915 against Staphylococcus aureus and 612 against Salmonella typlzosa; (b) exceptionally high hard water tolerance level of 850 parts per million; and (c) extensive testing under conditions simulating household laundering demonstrated that as little as 40 parts per million on the weight of the fabric was sutficient to prevent or arrest the growth of antibioticresistant strains of Staphylococcus aureus; and parts per million on the weight of the fabric sufliced to prevent or control diaper rash caused by ammonia-producing organisms.

In a softener formulation such as is commonly purchased and employed by housewives, about 4.5% of active cationic softener is present. A few ounces of such a prep- 3 aration is customarily introduced into the final rinse water in a domestic washing machine, such rinse water varying in quantity from about 10 to about 20 gallons. The cationic softener is absorbed or absorbed on the fabric, depending on the chemical nature of the latter.

Accordingly, mixtures were prepared for comparative testing which contained 6% by weight of 75% active softener, and also 2% by weight of the quaternary ammonium germicide described above. To some of these preparations, 2% by weight of a long chain fatty alcohol was added.

These mixtures were aged at ordinary room temperature until evidence of phase separation appeared, or for as long as eight months. Other samples were aged similarly at a temperature of 40 C. to simulate hot weather conditions. Formulations which appeared reasonably stable were subjected to at least one cycle of freezing and thawing after which they were set aside for observation for a period of weeks for evidence of phase separation.

Three separate commercial brands of di-(hydrogenated tallow) dimethyl ammonium chloride type softeners were used as controls in these tests. Since they all performed almost exactly alike, they will be treated as a single example, and will be referred to as D.T.C. Softener for the sake of brevity. Similarly, di-(hydrogenated tallow) dimethyl ammonium methosulfate will be abbreviated to D.T.Me. Softener.

The following examples, while not limiting the invention, will serve as illustrative embodiments:

EXAMPLE I A household laundry softener concentrate of 75 active content of the di-(hydrogenated tallow) dimethyl ammonium methosulfate type was formulated as follows in parts by weight:

D.T.Me. Softener 75% 6.0 BTC-2125 2.0 Lorol 2.0 Water 90.0

The formulation of Example I was altered by substituting for Lorol 5, a lauryl alcohol of commerce containing 80% of n-dodecanol. This formulation was appreciably less viscous in nature than its Lorol 5 counterpart. Under the above test conditions, it was fully as stable as that of Example I.

EXAMPLE III Where 2% of long chain fatty alcohol was employed in Examples I and II, reducing the fatty alcohol to 1.5% by weight yielded stable emulsions. However, 1% by weight of fatty alcohol reduced the stability, and 3% of fatty alcohol while exerting a stabilizing effect increased the viscosity of the mixture to a point which could handicap marketing such a product.

EXAMPLE 1V Formulation as follows, omitting the fatty alcohol:

D.T.Me. Softener 75 6.0 BTC-2125 2.0 Water 92.0

the emulsion broke down after two days at room temperature.

EXAMPLE. V

D.T.C. Softener 6.0 BTC-2125 2.0 Water 92.0

These mixtures were uniform emulsions when first prepared; phase separation was evident within 24 hours in every case.

EXAMPLE VI The softener concentrates of Example V were formu lated with fatty alcohol as follows:

D.T.C. Softener 75% 6.0 ETC-2125 2.0 Lorol 5 2.0 Water 90.0

These mixtures remained homogeneous at room temperature for two months, after which time some separa-.

tion occurred.

Other samples of the same maintained at 40 C. broke down after one month.

EXAMPLE VII The softener concentrates of Examples I and V were combined asfollows:

D.T.Me. Softener 75% 4.0 D.T.C. Softener 75% 2.0 BTC-2l25 2.0 Lorol 5 2.0 Water 90.0

These mixtures remained homogeneous for as long as six months at room temperature and four months at 40 C. Freezing and then thawing caused no damage.

The above examples demonstrate the. stabilization of a germicidal di-hydrogen-ated tallow softener, either of the chloride but preferably of the methosulfate type by the addition of not less than 1% nor more than 3% of a fatty alcohol such, for example, as is contained in the mixture of such alcohols as are obtained by reducing coconut fatty acids by hydrogenation or otherwise, such softener containing as a component a quaternary ammonium germicide of the benzalkouium type, and sp cifically a modified benzalkonium germicide of high potency.

They also demonstrate that a fatty alcohol which is predominantly dodecanol is equally as effective as mixed coconut alcohols.

They also demonstrate that the presence of moderate amounts of chloride ion in the presence of a preponderance of methosulfate ion does not necessarily impair the stabilizing effect of fatty alcoholor alcohols.

The. resistance of the above stabilized germicidal laundry softener to higher temperatures such as may be encountered in the summer season or to the cold of the ing of a fatty alcohol having 10 to 18 carbon atoms in the chain, said fabric softener having the structure:

wherein R and R are alkyl radicals having 10 to 20 carbon atoms, R" is a methyl radical, R' is a radical selected from the group of methyl, ethyl, and an ethoxylated radical having the structure (CH CH O),,H where n is an integer of at least 1, and X is an anion selected from the group consisting of chlorine, bromine, sulfate and methosulfate.

2. A stable microbiologically active laundry softener composition as defined in claim 1 wherein the fabric softener is di-(hydrogenated tallow) dimethyl ammonium methosulfate.

3. A stable microbiologically active laundry softener composition as defined in claim 1 wherein the fabric softener is (ii-(hydrogenated tallow) dimethyl ammonium chloride.

4. A stable microbiologically active laundry softener composition consisting essentially of a softeningly effective amount of di-(hydrogenated tallow) dimethyl ammonium salt, a microbiocidally effective amount of a benzalkonium salt having a phenol coefiicient of at least 200, and about 1 to 3% by weight of a coconut fatty alcohol having 10 to 18 carbon atoms.

5. A stable microbiologically active laundry softener composition as defined in claim 4 wherein the benzalkonium salt is selected from the group consisting of alkyl dimethyl benzyl ammonium chloride and alkyl dimethyl ethyl-benzyl ammonium chloride, said alkyl having 8 to 22 carbon atoms.

References Cited UNITED STATES PATENTS 3,093,591 6/1963 Freese 257-106 3,125,487 3/1964 Hutchinson 252-8.75 3,154,489 10/1964 DuBrow et al. 2528.8 X 3,247,119 4/1966 Herrick et a1. 252106 LEON D. ROSDO'L, Primary Examiner. J. T. FEDIGAN, Assistant Examiner.

Claims (1)

1. A STABLE MICROBIOCIDALLY ACTIVE LAUNDRY SOFTENER COMPOSITION CONSISTING ESSENTIALLY OF A SOFTENINGLY EFFECTIVE AMOUNT OF (1) A QUATERNARY AMMONIUM FABRIC SOFTENER, (2) A MICROBIOCIDALLY EFFECTIVE AMOUNT OF A QUATERNARY AMMONIUM SALT HAVING ONLY ONE ALKYL GROUP OF 8 TO 22 CARBON ATOMS ATTACHED TO THE QUATERNARY NITROGEN AND HAVING A PHENOL COEFFICIENT OF AT LEAST 200, AND (3) ABOUT 1 TO 3% BY WEIGHT OF AN EMULSIFYING AGENT CONSISTING OF A FATTY ALCOHOL HAVING 10 TO 18 CARBON ATOMS IN THE CHAIN, SAID FABRIC SOFTENER HAVING THE STRUCTURE: X-N(-R)(-R'')(-R")-R"'' WHEREIN R AND R'' ARE ALKYL RADICALS, HAVING 10 TO 20 CARBON ATOMS, R" IS A METHYL RADICAL, R"'' IS A RADICAL SELECTED FROM THE GROUP OF METHYL, ETHYL, AND AN ETHOXYLATED RDICAL HAVING THE STRUCTURE (CH2-CH2O)NH WHERE N IS AN INTEGER OF AT LEAST 1 AND X IS AN ANION SELECTED FROM THE GROUP CONSISTING OF CHLORINE, BROMINE, SULFATE AND METHOSULFATE.
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Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3472939A (en) * 1967-12-06 1969-10-14 Millmaster Onyx Corp Synergistic blends of microbiocidal quaternary ammonium compounds
US3489686A (en) * 1965-07-30 1970-01-13 Procter & Gamble Detergent compositions containing particle deposition enhancing agents
US3503890A (en) * 1966-07-29 1970-03-31 Staley Mfg Co A E Drain cleaner
US3525793A (en) * 1969-06-30 1970-08-25 Millmaster Onyx Corp Microbiocidal quaternary ammonium compounds containing synergistic blends of alkyl groups
US3625891A (en) * 1968-04-18 1971-12-07 Armour Ind Chem Co Wash cycle fabric softeners and method of preparing and using same
US3637495A (en) * 1966-08-01 1972-01-25 Henkel & Cie Gmbh Agent for the posttreatment of laundry
US3644204A (en) * 1967-08-14 1972-02-22 Henkel & Cie Gmbh Agent for the post-treatment of washed laundry
US3793196A (en) * 1971-03-31 1974-02-19 Lion Fat Oil Co Ltd Softening agent
DE2500111A1 (en) * 1974-01-11 1975-07-17 Procter & Gamble fabric softeners
US3896033A (en) * 1972-07-03 1975-07-22 Colgate Palmolive Co Encapsulated fabric softener
US3936537A (en) * 1974-11-01 1976-02-03 The Procter & Gamble Company Detergent-compatible fabric softening and antistatic compositions
FR2298600A1 (en) * 1975-01-25 1976-08-20 Hoechst Ag Softeners for textile materials
US3979307A (en) * 1972-09-20 1976-09-07 Texaco Inc. Fabric softener composition
FR2359928A1 (en) * 1976-07-26 1978-02-24 Unilever Nv Liquid compositions for materials deposited on the fabric surfaces
US4129506A (en) * 1975-09-04 1978-12-12 Hoechst Aktiengesellschaft Fabric softeners
FR2406690A1 (en) * 1977-10-22 1979-05-18 Cargo Fleet Chemical Co Composition based on a quaternary ammonium salt for softening fabrics and process for its preparation
US4213867A (en) * 1978-12-29 1980-07-22 Domtar Inc. Fabric conditioning compositions
EP0013780A1 (en) * 1979-01-11 1980-08-06 THE PROCTER & GAMBLE COMPANY Concentrated fabric softening composition
EP0041821A1 (en) * 1980-06-06 1981-12-16 THE PROCTER & GAMBLE COMPANY Granular fabric softening composition
US4321277A (en) * 1978-12-04 1982-03-23 Research Lab Products, Inc. Germicidal use of compositions containing certain quaternary ammonium compounds
FR2576614A1 (en) * 1985-01-30 1986-08-01 Colgate Palmolive Co Fabric softening composition based on a cationic softener and a fatty alcohol
US4661270A (en) * 1983-05-11 1987-04-28 Colgate-Palmolive Company Concentrated fabric softening composition and methods for making same
US4795032A (en) * 1987-12-04 1989-01-03 S. C. Johnson & Son, Inc. Wash-added, rinse-activated fabric conditioner and package
US4970008A (en) * 1988-12-20 1990-11-13 Kandathil Thomas V Fabric conditioner comprising a mixture of quaternary ammonium compounds and select tertiary amines
US5703035A (en) * 1994-02-23 1997-12-30 Witco Surfactants Gmbh Highly concentrated aqueous fabric softners having improved storage stability
US6180594B1 (en) 1998-12-01 2001-01-30 Witco Surfactants Gmbh Low-concentration, high-viscosity aqueous fabric softeners

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3093591A (en) * 1957-05-03 1963-06-11 Gen Mills Inc Compositions containing nu-alkyl-betaamino propionates and germicidal quaternary ammonium compounds
US3125487A (en) * 1964-03-17 Bacteriostatic compositions and meth-
US3154489A (en) * 1960-07-18 1964-10-27 Armour & Co Surface active compositions
US3247119A (en) * 1962-02-06 1966-04-19 Armour & Co Cleansing composition and thickener therefor

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3125487A (en) * 1964-03-17 Bacteriostatic compositions and meth-
US3093591A (en) * 1957-05-03 1963-06-11 Gen Mills Inc Compositions containing nu-alkyl-betaamino propionates and germicidal quaternary ammonium compounds
US3154489A (en) * 1960-07-18 1964-10-27 Armour & Co Surface active compositions
US3247119A (en) * 1962-02-06 1966-04-19 Armour & Co Cleansing composition and thickener therefor

Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3489686A (en) * 1965-07-30 1970-01-13 Procter & Gamble Detergent compositions containing particle deposition enhancing agents
US3503890A (en) * 1966-07-29 1970-03-31 Staley Mfg Co A E Drain cleaner
US3637495A (en) * 1966-08-01 1972-01-25 Henkel & Cie Gmbh Agent for the posttreatment of laundry
US3764531A (en) * 1966-08-01 1973-10-09 Henkel & Cie Gmbh Antimicrobial and laundry softening compositions
US3644204A (en) * 1967-08-14 1972-02-22 Henkel & Cie Gmbh Agent for the post-treatment of washed laundry
US3472939A (en) * 1967-12-06 1969-10-14 Millmaster Onyx Corp Synergistic blends of microbiocidal quaternary ammonium compounds
US3625891A (en) * 1968-04-18 1971-12-07 Armour Ind Chem Co Wash cycle fabric softeners and method of preparing and using same
US3525793A (en) * 1969-06-30 1970-08-25 Millmaster Onyx Corp Microbiocidal quaternary ammonium compounds containing synergistic blends of alkyl groups
US3793196A (en) * 1971-03-31 1974-02-19 Lion Fat Oil Co Ltd Softening agent
US3896033A (en) * 1972-07-03 1975-07-22 Colgate Palmolive Co Encapsulated fabric softener
US3979307A (en) * 1972-09-20 1976-09-07 Texaco Inc. Fabric softener composition
DE2500111A1 (en) * 1974-01-11 1975-07-17 Procter & Gamble fabric softeners
US3936537A (en) * 1974-11-01 1976-02-03 The Procter & Gamble Company Detergent-compatible fabric softening and antistatic compositions
FR2298600A1 (en) * 1975-01-25 1976-08-20 Hoechst Ag Softeners for textile materials
US4129506A (en) * 1975-09-04 1978-12-12 Hoechst Aktiengesellschaft Fabric softeners
FR2359928A1 (en) * 1976-07-26 1978-02-24 Unilever Nv Liquid compositions for materials deposited on the fabric surfaces
FR2406690A1 (en) * 1977-10-22 1979-05-18 Cargo Fleet Chemical Co Composition based on a quaternary ammonium salt for softening fabrics and process for its preparation
US4321277A (en) * 1978-12-04 1982-03-23 Research Lab Products, Inc. Germicidal use of compositions containing certain quaternary ammonium compounds
EP0015347A1 (en) * 1978-12-29 1980-09-17 Domtar Inc. Base mixes for fabric conditioning compositions and methods for their preparation
US4213867A (en) * 1978-12-29 1980-07-22 Domtar Inc. Fabric conditioning compositions
US4401578A (en) * 1979-01-11 1983-08-30 The Procter & Gamble Company Concentrated fabric softening composition
EP0013780A1 (en) * 1979-01-11 1980-08-06 THE PROCTER & GAMBLE COMPANY Concentrated fabric softening composition
EP0041821A1 (en) * 1980-06-06 1981-12-16 THE PROCTER & GAMBLE COMPANY Granular fabric softening composition
US4395342A (en) * 1980-06-06 1983-07-26 The Procter & Gamble Company Granular fabric softening composition
US4661270A (en) * 1983-05-11 1987-04-28 Colgate-Palmolive Company Concentrated fabric softening composition and methods for making same
US4772403A (en) * 1985-01-30 1988-09-20 Colgate Palmolive Company Fabric softener composition
FR2576614A1 (en) * 1985-01-30 1986-08-01 Colgate Palmolive Co Fabric softening composition based on a cationic softener and a fatty alcohol
DE3602089A1 (en) * 1985-01-30 1986-08-21 Colgate Palmolive Co Resistant aqueous pourable and water dispersible textilweichmachungszusammensetzung
DE3602089C3 (en) * 1985-01-30 2002-03-14 Colgate Palmolive Co Stable, pourable and water dispersible aqueous Textilweichmachungszusammensetzung
US4795032A (en) * 1987-12-04 1989-01-03 S. C. Johnson & Son, Inc. Wash-added, rinse-activated fabric conditioner and package
US4970008A (en) * 1988-12-20 1990-11-13 Kandathil Thomas V Fabric conditioner comprising a mixture of quaternary ammonium compounds and select tertiary amines
US5703035A (en) * 1994-02-23 1997-12-30 Witco Surfactants Gmbh Highly concentrated aqueous fabric softners having improved storage stability
US6180594B1 (en) 1998-12-01 2001-01-30 Witco Surfactants Gmbh Low-concentration, high-viscosity aqueous fabric softeners

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Owner name: MILLMASTER ONYX GROUP, INC., A DE CORP.

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:KEWANEE INDUSTRIES, INC.;REEL/FRAME:004139/0909

Effective date: 19830407

Owner name: BARCLAYS AMERICAN, 1 BUSINESS CREDIT, INC. 111 FOU

Free format text: SECURITY INTEREST;ASSIGNOR:MILLMASTER ONYX GROUP, INC., A DE CORP.;REEL/FRAME:004139/0941

Effective date: 19821222