US3749691A - Detergent-compatible,fabric-softening compositions - Google Patents

Detergent-compatible,fabric-softening compositions Download PDF

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US3749691A
US3749691A US3749691DA US3749691A US 3749691 A US3749691 A US 3749691A US 3749691D A US3749691D A US 3749691DA US 3749691 A US3749691 A US 3749691A
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fabric
softening
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detergent
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T Kandathil
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S C Johnson and Son Inc
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    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01BCABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B3/00Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
    • H01B3/18Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
    • H01B3/48Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances fibrous materials
    • 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
    • C11D1/88Ampholytes; Electroneutral compounds
    • C11D1/94Mixtures with anionic, cationic, or non-ionic 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
    • 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
    • C11D3/16Organic compounds
    • C11D3/37Polymers
    • C11D3/3746Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3749Polyolefins; Halogenated polyolefins; Natural or synthetic rubber; Polyarylolefins; Halogenated polyarylolefins
    • DTEXTILES; PAPER
    • D21PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21JFIBREBOARD; MANUFACTURE OF ARTICLES FROM CELLULOSIC FIBROUS SUSPENSIONS OR FROM PAPIER-MACHE
    • D21J1/00Fibreboard

Abstract

AQUEOUS, DETERGENT-COMPATIBLE, FABRIC-SOFTENING COMPOSITIONS ARE DESCRIBED AS COMPRISING (A) A CATIONIC SOFTENING AGENT, (B) AN AMPHOTERIC SURFACTANT, AND (C) A MODIFIED POLYOLEFIN EMULSION.

Description

United States Patent 3,749,691 DETERGENT-COMPATIBLE, FABRIC-SOFTENING COMPOSITIONS Thomas V. Kandathil, Racine, Wis., assignor to S. C. Johnson & Son, Inc., Racine, Wis.

No Drawing. Filed Dec. 31, 1970, Ser. No. 103,275 Int. Cl. Clld 3/28; D06m 15/26 US. Cl. 260-29.6 XA 11 Claims ABSTRACT OF THE DISCLOSURE Aqueous, detergent-compatible, fabric-softening compositions are described as comprising (A) a cationic softening agent, (B) an amphoteric surfactant, and (C) a modified polyolefin emulsion.

This invention relates to fabric-softening compositions. In one of its more specific aspects, this invention relates to aqueous, detergent-compatible, fabric-softening compositions.

Fabric-softening compositions (also referred to as fabric softeners) have been used in commercial and home laundry applications for the past few years. However, the presently available fabric-softening compositions generally require that they be added to the final rinse of the laundering process. If added directly to the wash cycle, these compositions do not produce the desirable or intended softening results. In addition, fabric softeners added to the Wash cycle tend to intefere with the detergent and, as a consequence, the cleaning may not be adequate. Unless the laundering machine is equipped with a dispenser for the fabric softener, a person must return to the laundry area to add these fabric softeners to the rinse cycle. Thus, it will be recognized that a detergent-compatible, fabricsoftening composition would be a highly useful product.

It is an object of this invention to provide a fabricsoftening' composition. Another object of this invention is to provide an aqueous, detergent-compatible, fabricsoftening composition. Still another object of this invention is to provide a detergent-compatible, fabric-softening composition having improved softening properties. Still another object of this invention is to provide a process for softening fabrics with an aqueous, detergent-compatible, fabric-softening composition. Yet still another object of this invention is to provide fabrics softened with an aqueous, detergent-compatible, fabric-softening composition. Other objects of this invention will appear herein.

These and other objects are attained by the practice of this invention, one embodiment of which comprises providing an aqueous, detergent-compatible, fabric-softening composition comprising:

(A) a cationic softening agent; (B) an amphoteric surfactant; and (C) a modified polyolefin emulsion.

Another embodiment of this invention comprises providing a process for softening fabrics, wherein said process comprises contacting said fabrics with the above-described aqueous, detergent-compatible, fabric-softening composition, which composition may be more specifically described as comprising:

(A) from about to about 30 percent, by weight, of a cationic softening agent;

(B) from about 1 to about 25 percent, by weight, of an amphoteric surfactant; and

(C) from about 0.25 to about 25 percent, by weight, of a modified polyolefin emulsion.

Still another embodiment of this invention comprises providing a fabric softened with an aqueous, detergentcompatible, fabric-softening componsition comprising:

(A) a cationic softening agent;

ICC

(B) an amphoteric surfactant; and (C) a modified polyolefin emulsion.

When the fabric-softening compositions of this invention are added to the wash cycle, the finished laundry is both clean and soft. This indicates that the detergent and fabric softener are not interfering with each other. It is this type of interference which tends to result in a substantial loss of detergent and softening capabilities.

An essential component of the fabric-softeners of this invention is cationic softening agent (that is, softening agents having an active cation). These agents contain one or two nitrogen atoms quaternized with reactants having groups such as sulfate, nitrate, nitrite, halide (e.g., chloride, bromide, fluoride, or iodide), phospshate, and carbonate.

The cationic softening agents useful in this invention are those derived, in part, from a fatty acid having at least 12 carbon atoms. Among the useful cationic softening agents are (a) the dialkyl imidazolinium methosulfates, including the l-methyl-1-alkylamidoethyl-2-alkyl-imidazolinium methosulfates and (b) the dialkyl dimethyl quaternary ammonium chlorides.

Specific commercially available cationic softening agents falling in category (a) include Varisoft 475 and Varisoft 222 from Varney Chemical Division of Northern Petrochemical Company, Armosoft AB from Armour Industrial Chemical Company, and Ammonyx 4080 from Onyx Chemical Company. Specific commercially available cationic softening agents falling in caegory (b) include Armosoft 2HT and Armosoft DC from Armour.

The cationic softening agents falling in category (3.) may also be described as having the general formula:

wherein D is a divalent, non-amino, organic group having 1-24 carbon atoms and composed of elements from the group consisting of C, H, O, and N; D is a divalent organic group having 1-24 carbon atoms, composed of elements from the group consisting of C, H, O, and N, and containing at least one amino group; R is hydrogen, an alkyl group having 1-24 carbon atoms, or a cycloalkyl group having 1-24 carbon atoms (such as methyl, ethyl, propyl, butyl, hexyl, decyl, lauryl, myrisityl, palmityl, stearyl, tetracosanyl, cyclopentyl, cyclohexyl, oleyl, linoleyl); R is an alkyl group having 1-24 carbon atoms or an aralkyl group having 1-24 carbon atoms (such as methyl, propyl, lauryl, stearyl, tetracosanyl, hydroxyethyl, hydroxypropyl, fluoromethyl, bromoethyl, benzyl, cinnamyl), with the provision that at least two of R and R are alkyl groups having at least 11 carbon atoms; A represents an anion; and Y and Z are each hydrogen or alkyl groups having 1-6 carbon atoms (such as methyl, ethyl, propyl, pentyl, hexyl). A preferred D group is -CH CH and a preferred D group is amidoethyl.

Suitable anions include anions derived from sulfates, nitrates, nitrites, phosphates, carbonates, and halides (such as chloro, bromo, fiuoro and iodo).

Examples of useful cationic softening agents are disclosed in US. Pats. 2,874,074 and 2,995,520; British Pat. 985,321; and McCutcheons Detergents and Emulsifiers 1970 Annual.

An especially preferred cationic softening agent is 2- heptadecyl 1 methyl 1 (stearyl amidoethyl)imidazolinium methosulfate.

The fabric-softening compositions of this invention generally comprise from about 5 to about 30 percent, by weight, of the cationic softening agent. A preferred range is from about -25 percent, by weight. Blends of cationic softening agents can be used.

Another essential component of these fabric softeners is an amphoteric surfactant. Because it contains an active cation and an active anion, this type of surfactant functions as a cationic surfactant in acid media and as an anionic surfactant in alkaline media. Amphoteric surfactants, in addition to contributing to the softening capability of these fabric softeners, provide the following special advantages: have no adverse effect on lightfastness or shade of dyestuffs; are resistant to yellowing during high temperature drying; produce no yellowing or rancidity of stored fabrics; gives excellent chemical stability over the pH range of these fabric softeners; and give antistatic effects on fabrics.

Amphoteric surfactants useful in the practice of this invention include the complex fatty amido surfactants having the general formula:

wherein R is an alkyl group having 12-18 carbon atoms (such as lauryl, tridecyl, tetradecyl, pentadecyl, palmityl, heptadecyl, stearyl, ethyl, lauryl, oleyl, and linoleyl), R is a divalent aliphatic hydrocarbon group having 2-5 carbon atoms (such as methylene, ethylene, propylene, butylene, 2-methylbutylene, and pentylene), R is a divalent aliphatic hydrocarbon group having l-S carbon atoms (such as methylene, ethylene, propylene, butylene, 2-methylbutylene, and pentylene), and M is a hydrogen or an alkali metal (such as sodium, potassium, calcium, and lithium).

From the immediately preceding general formula, it will be recognized that R, R and R can be branched or unbranched and that R can be saturated or unsaturated.

Commercially available amphoteric surfactants useful in this invention include Miranol CM (liquid) and Miranol DM (paste), both having the formula:

O CHzCOONa from Miranol Chemical Co., Inc.; Soromine AL and Soromine AT from GAF Corporation; and the Deriphat compounds from General Mills, Inc.

Useful amphoteric surfactants are disclosed in U .8. Pat. 2,528,378 and in McCutcheons Detergents and Emulsifiers 1970 Annual.

The fabric softeners of this invention generally comprise from about 1 to about 25 percent, by weight, of the amphoteric surfactant. A preferred range is from about 2.5 to about percent, by weight, A blend of amphoteric surfactants may be used.

A third essential component of these fabric softeners is a modified polyolefin emulsion, preferably a modified polyethylene or polypropylene emulsion. The term modified indicates that the polyolefin is at least partially oxidized and, with the aid of emulsifying agents, formed into an emulsion. Depending upon the nature of the emulsifier used, the modified polyolefin emulsion may be nonionic, cationic, or anionic. The fabric softeners of this invention may contain a blend of these emulsions.

The modified polyolefin may contain functional groups, such as carboxyl, alkylamide, SulfOnic acid, and amide.

Examples of modified polyolefins which can be emulsified and used in the practice of this invention include polyethylene; polypropylene; high density polyethylenes; and copolymers of polyethylene and acrylic acid or a substituted acrylic acid. These modified polyolefins are commercially available from such sources as Eastman Chemical Products, Inc. (including the Epolene series) and Allied Chemical Company (including the AC series).

These emulsions generally have a solids content (including the modified polyolefin) of about 10 to about 35 percent, by weight. A preferred range is about 15 to about 30 percent, by weight.

If the modified polyolefin emulsions are prepared by using emulsifiers which contain ethylene oxide units, these emulsifiers can contain up to 16 moles of ethylene oxide.

The fabric-softening compositions of this invention generally comprise from about 0.25 to about 25 percent, by weight, of the modified polyolefin emulsion. A preferred range is from about 0.5 to about 20 percent, by weight.

These fabric softeners generally have a viscosity from about 50 to about 3500 centipoises (measured using a Brookfield viscometer, RVF model, at 20 r.p.m. with a #2 spindle) and a pH from about 3.5 to about 7.0.

Minor amounts (from about 0.001 to about 5.0 percent, by weight) of optional components may be used to enhance or provide particular characteristics to these fabric softeners. Examples of such optional components include viscosity-controlling agents, humectants, fluorescent whitening agents, bactericides, perfumes, wetting agents, preservatives, anti-foaming agents, dispersing aids, and dyes.

The viscosity-controlling agents suitable for use in this invention are selected from the group consisting of metal salts of aliphatic, monocarboxylic acids having 14 carbon atoms; metal halides; and mixtures thereof. Examples of the acid salts are sodium, calcium, potassium, aluminum, and ammonium acetates; sodium, calcium, potassium, aluminum, and ammonium propionates; sodium, calcium, potassium, aluminum, and ammonium formates; and sodium, calcium, potassium, aluminum, and ammonium butyrates. Examples of the metal halides are sodium, calcium, potassium, aluminum, and ammonium chlorides; sodium, calcium, potassium, aluminum, and ammonium bromides; sodium, calcium, potassium, aluminum, and ammonium iodides; and sodium, calcium, potassium, aluminum, and ammonium fluorides. A mixture of these agents may be used. A preferred viscosity-controlling agent is sodium chloride.

Various humectants may be used to improve the water absorbency of the fabrics treated with these fabric softeners. Examples of such humectants are glycerin, polymethylene glycols having 26 carbon atoms (such as ethylene, trimethylene, tetramethylene, pentamethylene, and hexymethylene glycols) and mixtures thereof. An especially preferred humectant is ethylene glycol.

Another optional component is a fluorescent whitening agent to improve the apparent whiteness and brightness of the cleaned and softened fabrics. Examples of suitable fluorescent whitening agents are sold by Sandoz, Inc., under the trade designation Sandoz TH-40; by GAF Corporation under the trade designation Blancophore; by American Cyanamid under the trade designation Calcofluor; by Geigy Chemical Company under the trade designation Tinopal; and by Ciba under the trade designation Uvitex. Blends of these agents may be used.

For an average load (3-5 pounds) of clothes to be washed and softened, from about one-half to about ten ounces of these fabric softeners can be added to the wash cycle of an automatic washing machine. The specific amount to be added will necessarily depend upon such variables as the washing condition and the amount of clothes to be washed and softened. A preferred amount of fabric softener is from 1-5 ounces.

The fabric softeners of this invention are stable (i.e., do not separate into phases in the container) for periods up to 3 months and longer.

A useful procedure for preparing the fabric-softening compositions of this invention is as follows: With mild agitation, the amphoteric surfactant is added to warm water (at least 90 F.). While continuing the agitation, the warm (at least 90 F.) cationic softening agent is added to the surfactant-water blend. Finally, the modified polyolefin emulsion is added to the surfactant-watersoftening agent blend. Optional components can be added while cooling the final blend to room temperature.

The compositions of this invention soften fabrics containing fibers of various types-such as cellulosics (e.g., cotton), and synthetics. Examples of synthetic fibers include polyesters (such as Kodel polyester sold by Eastman Chemical Products, Inc., and Dacron polyester sold by DuPont), and polyamides (such as nylon).

If desired, these fabric softeners can be added to the rinse cycle and equivalent softening will be obtained as when added to the wash cycle.

A preferred method of using these fabric softeners in an automatic washing machine is to fill the wash tub with about two inches of water and then add the fabric softener. After the addition of fabric softener is completed and, as the wash tub is being filled with the remaining water, the laundry is placed in the machine and then the detergent is added.

The following standard test may be used to demonstrate that the fabric softeners of this invention do provide (1) softness in the presence of detergents and (2) improved softness over other softening compositions:

Two laundry bundles (A and B) of about 4 pounds each and containing such items as Turkish towels (which are good exhibitors of softness), pillow cases, shirts, etc., are prepared. Bundle A is washed with detergent, but no fabric softener, in an automatic washing machine. Bundle B is washed in an identical manner, but with about 3 /2 ounces of a fabric softener of this invention being added during the wash cycle. A panel of -12 members is then asked to determine the difference in softness between bundles A and B.

The above standard test may be altered by adding, during the wash cycle, a prior fabric softener (that is, not one of this invention) to bundle A. The panel is then asked to determine the difference in softness between bundles A and B.

This invention will be further illustrated by the following examples of preferred embodiments. However, it will be understood that these examples are included for purposes of illustration and are not intended to limit the scope of this invention.

Unless otherwise indicated, all percentages are by In the above examples: The blue dye is an oil-soluble blue dye. The anti-foaming agent is a 10 percent silicone anti-foaming agent. 31-6 is a dye formulation consisting of 99.33 percent isopropyl alcohol and 0.67 percent of the oil-soluble blue dye. 126-2" is an oxidized polyethylene emulsion consisting of 69.092 percent water, 20.000 percent polyethylene (sold by Allied Chemical Company under the trade designation AC-629), 5.000 percent nonylphenoxypoly(ethyleneoxy)ethanol, 5.000 percent diethylene glycol, 0.708 percent of a 45% potassium hydroxide solution, and 0.200 percent of a 37% formaldehyde solution.

While laundry bundles of clothing are being laundered in an automatic washing machine, the above eight compositions are added during the wash cycle. The laundering is completed, and the clothes are then dried. The clothes are clean, bright-looking, and soft. There is no interference between the detergent and the softener.

Thus, it will be recognized that the fabric-softeners of this invention permit the user to obtain softness in the presence of detergents and detergency in the presence of softness.

Although this invention has been described in detail with particular reference to preferred embodiments thereof, it will be understood that variations and modifications can be effected within the spirit and scope of this invention as described hereinabove and as defined in the appended claims.

I claim:

1. An aqueous, detergent-compatible, fabric softening composition comprising:

(A) from about 5 to about 30 percent, by weight, of a cationic softening agent containing one or two quaternized nitrogen atoms and being derived in part from a fatty acid having at least 12 carbon atoms;

(B) from about 1 to about 25 percent, by weight, of an amphoteric surfactant having the general formula:

weight. N-E-Y EXAMPLES 1-8 R 0% A The following eight fabric-softening compositions are prepared to contain the percentages shown of each component: DR Z Percent in- Component Example 1 ExampleZ ExampleB Example4 Examplefi Example6 Example7 Example 8 Sodium chloride 0.200 0. 200 0.200 0. 200 0. 200 0.200 72. 248 72. 298 72. 438 72. 488 72. 72.

Fluorescent whitening agent 0.200 0.200 0. 200 0. 200 0.200 0.200 Anti-foaming agent 0. 050 0.050 0.050 31-6 0.300 0.300 126- 4. 000 4. 000 4. 000 4. 000 4. 000 4. 000 Ethylene glycol 1.000 1.000 1 000 1. 000 1.000 1.000 Peri e 0.300 0.300 0.300 0.300 0.300 0.300

Total 100.000 100.000 100. 000 100. 000 100. 000 100.000

wherein D is -CH CH D is amidoethyl; R is hydrogen, an alkyl group having 124 carbon atoms, or a cycloalkyl group having 1-24 carbon atoms; R is an alkyl group having 1-24 carbon atoms or an aralkyl group having 1-24 carbon atoms, with the provision that at least two of R and R are alkyl groups having at least 11 carbon atoms; A represents an anion; and Y and Z are each hydrogen or alkyl groups having 1-6 carbon atoms.

3. A composition as defined by claim 1 wherein R is methylene and each M is sodium.

4. A composition as defined by claim 1 wherein said polyolefin emulsion is a polypropylene emulsion.

5. A composition as defined by claim 1 wherein said cationic softening agent is Z-heptadecyl-l-methyl-l-stearylamidoethylimidazolinium methosulfate.

6. A composition as defined by claim 1 wherein said emulsion is a polyethylene emulsion.

7. An aqueous, detergent-compatible, fabric softening composition comprising:

(A) from about 5 to about 30 percent, by weight of a cationic softening agent containing one of two quaterm'zed nitrogen atoms and being derived in part from a fatty acid having at least 12 carbon atoms;

(B) from about 1 to about 25 percent, by weight, of an amphoteric surfactant having the general formula:

CH1 t 9H2 R- J-I i-R OM ofim-oo OM wherein R is an alkyl group having 12l8 carbon atoms, R is an aliphatic hydrocarbon group having 2-5 carbon atoms, R is an aliphatic hydrocarbon group having 1-5 carbon atoms, and each M is hydrogen or an alkali metal;

(C) from about 0.25 to about 25 percent, by weight, of a polyolefin emulsion, said polyolefin being selected from the group consisting of polyethylene and polypropylene and being at least partially oxidized;

(D) from about 0.001 to about 5 percent, by weight, of a viscosity-controlling agent selected from the group consisting of metal salts of aliphatic, monocarboxylic acids having 1-4 carbon atoms; metal halides; and mixtures thereof;

(E) from about 0.001 to about 5 percent, by weight,

of a fluorescent whitening agent; and

(F) from about 0.001 to about 5 percent, by weight, of a humectant selected from the group consisting of polymethylene glycols having 2-6 atoms, glycerin, and mixtures thereof.

8. A composition as defined by claim 7 wherein said cationic softening agent is Z-heptadecyl-l-methyl-l-stearyl amidoethylimidazolinium methosulfate.

9. A composition as defined by claim 8 wherein said polyolefin emulsion is a polyethylene emulsion.

10. A composition as defined by claim 7 wherein said viscosity-controlling agent is sodium chloride.

11. A composition as defined by claim 7 wherein said humectant is ethylene glycol.

References Cited UNITED STATES PATENTS 3,537,993 11/1970 Coward et a1. 252-8.75 3,245,831 4/ 1966 Shippee 117-1395 2,528,378 10/1950 Mannheimer 252542 X 3,509,049 4/1970 Zweidler 2528.8 X 3,033,704 5/1962 Sherrill et al 252106 X 3,451,927 6/1969 Tune 2528.8 X

HERBERT B. GUYNN, Primary Examiner U.S. Cl. X.R.

117139.5 A, 139.5 CQ; 2528.75, 8.8, 89, 542, 547; 26029.6 MN

UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No. 9, 9 L Dated July 31, 1973 I r1 ventor(s) Thomas V. Kandathil I g It, is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:

In Column 1, line 28, change "intefere" to "interfere".

In Column 1, line 71, change componsition to composition.

In Column 2, line 29, change caegory to category.

In Column 2, lines 71 -72, and Column 3, lines 58-59, Detergents Emulsifiers 197Q Annual should be set off as a title.

In Column 3, line 63, change the comma after "weight" to a period.

In Claim 5, line 3, and Claim 8, line 3, change amidoethylimidazolinium to amidoethyl -im idazo1inium.

In Claim 7, line 4', change of to or.

In Claim 9, line '1, change Claim 8 to Claim 7.

Signed and sealed this 9th day of April 1971;.

(SEAL) Attest:

EDWAP I-I.FLETCPER,JR I C MARSHALL DANN Attesting Officer Commissioner of Patents FORM PC4050 USCOMM-DC 60376-P69 U.S. GOVERNMENT PRINTING OFFICE I919 0-368-334,

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US3835148A (en) * 1971-02-16 1974-09-10 Ciba Geigy Ag Aqueous polystyrene containing dispersions as anti-statics for the permanent finishing of fibre materials
US3910759A (en) * 1972-08-25 1975-10-07 Gaf Corp Method of treating fabrics
US3936538A (en) * 1974-03-18 1976-02-03 Calgon Consumer Products Company Inc. Polymeric film dryer-added fabric softening compositions
US3983061A (en) * 1971-02-16 1976-09-28 Ciba-Geigy Corporation Process for the permanent finishing of fiber materials
US3984335A (en) * 1975-01-16 1976-10-05 Basf Wyandotte Corporation Compositions for souring and softening laundered textile materials and stock solutions prepared therefrom
US3998775A (en) * 1975-04-24 1976-12-21 Allied Chemical Corporation Aerosol latex paint containing imidazoline surfactants
US4121009A (en) * 1974-09-03 1978-10-17 Gaf Corporation Anti-static fabric softening compositions and processes for drying and softening textiles therewith
US4127489A (en) * 1976-05-20 1978-11-28 The Procter & Gamble Company Process for making imidazolinium salts, fabric conditioning compositions and methods
US4233451A (en) * 1976-05-20 1980-11-11 The Procter & Gamble Company Process for making imidazolinium salts
US4666964A (en) * 1983-12-16 1987-05-19 Calgon Corporation Method for producing free-flowing water-soluble polymer gels
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
US5051250A (en) * 1989-06-21 1991-09-24 Colgate-Palmolive Company Fiber conditioning compositions containing solubilized poly-lower alkylene
US5494593A (en) * 1992-07-17 1996-02-27 Clariant Finance (Bvi) Limited Amphoteric surfactants-containing wax compositions, their production and their use
WO1997028239A1 (en) * 1996-01-31 1997-08-07 The Procter & Gamble Company Fabric care compositions including dispersible polyolefin and method for using same
WO1997028242A1 (en) * 1996-01-31 1997-08-07 The Procter & Gamble Company Laundry additive compositions including dispersible polyolefin and method for using same
WO1997028244A1 (en) * 1996-01-31 1997-08-07 The Procter & Gamble Company Process for making a fluid, stable liquid fabric softening composition including dispersible polyolefin

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GB1596791A (en) * 1977-02-15 1981-08-26 Unilever Ltd Deodorant detergent composition
DE3209239A1 (en) * 1981-03-23 1982-09-30 Sandoz Ag Composition for accelerating the drying of hydrophilic materials
GB8823875D0 (en) * 1988-10-12 1988-11-16 Dow Corning Sa Softening compositions
DE4435386A1 (en) * 1994-10-04 1996-04-11 Henkel Kgaa Aqueous fabric softener dispersions

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3835148A (en) * 1971-02-16 1974-09-10 Ciba Geigy Ag Aqueous polystyrene containing dispersions as anti-statics for the permanent finishing of fibre materials
US3983061A (en) * 1971-02-16 1976-09-28 Ciba-Geigy Corporation Process for the permanent finishing of fiber materials
US3910759A (en) * 1972-08-25 1975-10-07 Gaf Corp Method of treating fabrics
US3936538A (en) * 1974-03-18 1976-02-03 Calgon Consumer Products Company Inc. Polymeric film dryer-added fabric softening compositions
US4121009A (en) * 1974-09-03 1978-10-17 Gaf Corporation Anti-static fabric softening compositions and processes for drying and softening textiles therewith
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WO1997028242A1 (en) * 1996-01-31 1997-08-07 The Procter & Gamble Company Laundry additive compositions including dispersible polyolefin and method for using same
WO1997028244A1 (en) * 1996-01-31 1997-08-07 The Procter & Gamble Company Process for making a fluid, stable liquid fabric softening composition including dispersible polyolefin
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Also Published As

Publication number Publication date Type
FR2120168A1 (en) 1972-08-11 application
GB1360660A (en) 1974-07-17 application
NL7118110A (en) 1972-07-04 application
CA965905A1 (en) grant
DE2165947A1 (en) 1972-07-20 application
CA965905A (en) 1975-04-15 grant

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