US3928213A - Fabric softener and soil-release composition and method - Google Patents

Fabric softener and soil-release composition and method Download PDF

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Publication number
US3928213A
US3928213A US375218A US37521873A US3928213A US 3928213 A US3928213 A US 3928213A US 375218 A US375218 A US 375218A US 37521873 A US37521873 A US 37521873A US 3928213 A US3928213 A US 3928213A
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composition
alkyl
carbon atoms
weight
cellulose
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US375218A
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Robert Dwight Temple
Vincent Paul Heuring
James Bruce Prentice
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Procter and Gamble Co
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Procter and Gamble Co
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Priority to US375218A priority Critical patent/US3928213A/en
Priority to CA195,104A priority patent/CA1024703A/en
Priority to DE2413042A priority patent/DE2413042B2/de
Priority to GB1283674A priority patent/GB1459935A/en
Priority to CH406974A priority patent/CH603788A5/xx
Priority to IT42532/74A priority patent/IT1005781B/it
Priority to AT239574A priority patent/AT347552B/de
Priority to FR7410015A priority patent/FR2222476B1/fr
Priority to NL7403897A priority patent/NL7403897A/xx
Priority to JP49033057A priority patent/JPS5035495A/ja
Priority to BE142415A priority patent/BE812785A/xx
Priority to CA202,583A priority patent/CA1027713A/en
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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
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/01Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
    • D06M15/03Polysaccharides or derivatives thereof
    • D06M15/05Cellulose or derivatives thereof
    • D06M15/09Cellulose ethers
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR 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
    • D06M13/46Compounds containing quaternary nitrogen atoms

Definitions

  • This invention relates to fabric conditioning compositions and to a method of conditioning textile materials. More particularly, it relates to compositions adapted to the provision of fabric softening and antisoiling properties and useful in the repetitious but generally discontinuous laundering process which involves soiling, laundering, rinsing, soiling, etc.
  • Fabric softening compositions useful for this purpose have for the most part been liquid fabric softener compositions containing in a water vehicle a quaternary ammonium salt component having an affinity for negativelycharged fibers and having at least one long chain alkyl moiety of from 16 to 20 carbon atoms. These compositions have been largely adapted for use in the final rinsing bath of the home laundering process. It has been found that the treatment of textile materials in such manner improves the softness or feel of the treated fabrics, prolongs the useful life of the textile materials and reduces the tendency of the fabrics to accumulate electrical charges.
  • Another object, of the invention is to provide a method whereby fabrics can be effectively softened and rendered anti-soiling by treatment in a laundry rinsing operation.
  • the present invention is based in part upon the discovery that fabrics can be improved in feel by treating the fabrics in anaqueous rinsing bath containing a cationic fabric softening agent and a minor amount of an hydroxyalkyl alkyl cellulose or alkyl cellulose antisoiling agent.
  • the present invention provides an aqueous fabric softener composition consisting essentially of A. from 2% to 15% of a cation-active fabric softening compound having from one to two straight chain organic groups of from 8 to 22 carbon atoms;
  • an anti-soiling agent selected from the group consisting of hydroxyalkyl alkyl cellulose and alkyl cellulose where each alkyl has from 1 to 3 carbon atoms, said anti-soiling agent having a viscosity of less than about 400 centipoises as determined at a 2% by weight concentration in water and at 20C;
  • an emulsifier selected from the group consisting of l) the condensation product of one mole of alkylphenol wherein the alkyl chain contains from about 8 to about 18 carbon atoms with from about one to about moles of ethylene oxide, (2) the condensation product of one mole of an aliphatic alcohol wherein the alkyl chain contains from about 10 to about 24 carbon atoms with from about one to about 100 moles of ethylene oxide, (3) polyethylene glycols having a molecular weight of from about 1400 to about 30,000, and (4) mixtures thereof; and
  • the present invention provides a method of simultaneously imparting softening and antisoiling properties to washed textiles which comprises treating previously-washed textiles in an aqueous rinsing bath containing minor but effective amounts of a cation-active fabric softening agent having from one to two straight chain organic groups of from 8 to 22 carbon atoms and an anti-soiling agent as hereinbefore defined.
  • compositions of this invention provide fabricsoftening properties to treated textiles and anti-soiling effects by the application of anti-soiling agent, e.g., hydroxypropyl methyl cellulose, onto the treated fabrics from an aqueous rinsing bath of a laundering process.
  • anti-soiling agent e.g., hydroxypropyl methyl cellulose
  • the compositions are sufficiently fluid as to permit ready measurement, pouring and dispersibility in water.
  • the cation-active organic fabric-softener compounds which are the principal fabric-softening components of the compositions of the invention, are known fabric-softening compounds. Generally, these comprise cationic nitrogen-containing compounds such as quaternary ammonium compounds and amines and have one or two straight-chain organic groups of at least eight carbon atoms. Preferably, they have one or two such groups of from 12 to 22 carbon atoms.
  • Preferred cation-active softener compounds include the quaternary ammonium softener compounds corre sponding to the formula wherein R'is hydrogen or an aliphatic group of from 1 to 22 carbons; R is an aliphatic group having from 12 to 22 carbon atoms; and X is an anion selected from halogen, acetate phosphate, nitrate and methyl sulfate radicals.
  • preferred cationic softener compounds of the invention are the dialky! dimethyl ammonium chlorides, wherein the alkyl groups have from 12 to 22 carbon atoms and are derived from long'chain fatty acids, such as hydrogenated tallow.
  • alkyl is intended as including unsaturated compounds such as are present in alkyl groups derived from naturally occurring fatty oils.
  • tallow refers to fatty alkyl groups derived from tallow fatty acids. Such fatty acids give rise to quaternary softener compounds wherein R and R have predominantly from 16 to 18 carbon atoms.
  • coconut refers to fatty acid groups from coconut oil fatty acids...
  • the coconutalkyl R and R groups have from about 8 to about 18 carbon atoms and predominate in C to C alkyl groups.
  • Representative examples of quaternary softeners of the invention include tallow trimethyl ammonium chloride; ditallow dimethyl ammonium chloride; ditallow dimethyl ammonium methyl sulfate; dihexadecyl dimethyl ammonium chloride; di(hydrogenated tallow) dimethyl ammonium chloride; dioctadecyl dimethyl ammonium chloride; dieicosyl dimethyl ammonium chloride; didocosyl dimethyl ammonium chloride; di(hydrogenated tallow) dimethyl ammonium methyl sulfate; dihexadecyl diethyl ammonium chloride; dihexadecyl dimethyl ammonium acetate; ditallow dipropyl ammonium phosphate; ditallow dimethyl
  • An especially preferred class ,of quaternary ammonium softeners of the invention corresponds to the formula RI cH, T cH, x 1
  • R and R are each straight chain aliphatic groupsof from 12 to 22 carbon atoms and X is halogen
  • chloride e.g., chloride.
  • ditallow dimethyl ammonium chloride di(hydrogenated tallowalkyl) dimethyl ammonium chloride and di(coconut- 4 pylene diamine; soya 1,3-propylene diamine and the like.
  • Suitable cation-active softener compounds herein are the quaternary imidazolinium salts.
  • Preferred salts are those conforming to the formula wherein R is an alkyl containing from 1 to 4, preferably from 1 to 2, carbon atoms, R is an alkyl containing from 1 to 4 carbon atoms or a hydrogen radical, R is an alkyl containing from 8 to 22, preferably at least 15, carbon atoms, R,, is hydrogen or an alkyl containing from 1 to 22, preferably at least 15, carbon atoms, and X is an anion, preferably methyl sulfate or chloride ions.
  • Other suitable anions include those disclosed with reference to the cationic quaternary ammonium fabric softeners described hereinbefore.
  • cationic quaternary ammonium fabric softeners which are useful herein include, for example, alkyl (C, to C )-pyridinium chlorides, alkyl (C to C alkyl (C to C;,)-morpholinium chlorides, and quaternary derivatives of amino acids and amino esters.
  • the cationic fabric softeners mentioned above can be used singly or in combination in the practice of the present invention.
  • the cationic fabric softener comprises from about 2% to about 15% by weight of the total composition. If more than about 15% is used, product stability problems may occur, e.g., thickening and the possible formation of an undesired gel and if less than about 2% is used, the softener will be too dilute and desired softening of the fabrics will not be achieved when conventional amounts of the composition are added to the wash water. Within the above range, the actual amount of fabric softener which is contained in the composition depends upon the desired usage concentration of the composition in a laundering process.
  • a desired concentration of the fabric softener in the rinsing solution is from about 25 ppm to about 100 ppm.
  • the preferred range of cationic fabric softener in the rinsing solution is from about 35 ppm to about ppm.
  • the preferred range of cationic fabric softeper is from about 2.5% to about 6% by weight of the total composition.
  • the anti-soiling agents suitable for use in the compositions of the present invention include hydroxyalkyl alkyl cellulose and alkyl cellulose where the alkyl in each instance has from 1 to 3 carbon atoms. These anti-soiling agents are derived from cellulose and can be described as cellulose having substituent groups on the hydroxyls of the anhydroglucose units.
  • the basic structure of cellulose which forms the backbone of the antisoiling agents of the invention may be depicted as follows, wherein n is a finite number:
  • the number of substituent groups of the hydroxyls of the anhydroglucose units of cellulose can affect a number of properties, such as solubility and gel point.
  • Substituent groups can be designated by weight percent or by the number of points where groups are attached to the hydroxyls, otherwise termed degree of substitution (D.S. If all three available positions on each unit are substituted, the D8. is designated as (3) three; if an average of two on each ring are reacted, the D8. is designated (2) two, etc.
  • cellulose fibers from cotton linters or wood pulp, are swelled by caustic soda solution to produce alkali cellulose which is then treated with alkyl chloride, e.g., methyl chloride, yielding the alkyl ether of cellulose, e.g., methyl cellulose.
  • alkyl chloride e.g., methyl chloride
  • a preferred anti-soiling agent of the invention is an hydroxyalkyl alkyl cellulose which is prepared by swelling cotton linters or wood pulp with a caustic soda solution to produce alkali cellulose which is treated with an alkylchloride, e.g., methyl chloride, and an alkylene oxide, e.g., propylene oxide which leads to a substituent group having a secondary hy-.
  • an alkylchloride e.g., methyl chloride
  • an alkylene oxide e.g., propylene oxide which leads to a substituent group having a secondary hy-.
  • CH OH OCH Especially suitable is such a material wherein the methoxyl substitution corresponds to from 27% to 30% by weight and propylene glycol ether substitution amounts to 7% to 12% by weight.
  • Anotherpreferred anti-soiling agent is methyl cellulose. These preferred materials are commercially available under the name Methocel (The Dow Chemical Company).
  • the anti-soiling agents of the invention are characterized by molecular weights which can be expressed in terms of their viscosity grades measured with a Ubbelohde tube as a 2% by weight aqueous solution at 20C. It will be appreciated that the viscosity that such materials will produce in solution depends on the length of the polymer chain.
  • Suitable anti-soiling agents herein are those which provide a viscosity grade as defined hereinbefore of less than about 400 centipoises. Preferably, they have a viscosity grade of less than about 100 centipoises.
  • the amount of anti-soiling agent employedto provide effective soiland stain-release properties will depend on such factors as the particular softening agent employed, the nature of the anti-soiling agent and its molecular weight or viscosity and the desired viscosity or physical appearance of the finished composition. As little as 0.1% of the anti-soiling agent based on the weight of composition may be enough in some instances, whereas up to about 10% may be required in others.
  • the anti-soiling agent comprises fromabout 0.25% to about 5% of the composition.
  • an amount of a composition of the invention ca orr is added to the rinsing cycle of a laundering operation as to provide a concentration of the anti-soiling agent of from 2 to 100 ppm. Preferably, the concentration is from 5 to 50 ppm.
  • compositions of the invention can be formulated in a convenient manner to provide uniform and homogeneous compositions of viscosity below about 250 centipoises.
  • the viscosity is in a range of from 30 to 180 centipoises.
  • a solution of the anti-soiling agent is prepared by adding the agent to water at an elevated temperature. The temperature is then lowered sufficiently as to cause the anti-soiling agent, having inverse temperature solubility characteristics, to go into solution. The remaining ingredients,
  • fabric softening agent emulsifying agent and minor optional ingredients are added.
  • the antisoiling agent can be admixed with all the organic constituents of the finished composition and the resulting mixture be added with stirring to water to provide a finished composition.
  • the anti-soiling agents of the invention retain their desirable soiland stainrelease properties at relatively low molecular weights, corresponding to viscosities of less than 400 centipoises in a 2% aqueous solution. Accordingly, they can be efiectively employed in fabric softening compositions where the viscosity of the finished composition is less than about 250 centipoises.
  • cellulosederived anti-soiling agents of the prior art e.g., hydroxypropyl cellulose
  • the molecular weight of such anti-soiling agents is frequently so high as to provide the finished composition with an unacceptable viscosity, i.e., above about 250 centipoises. 1f the molecular weight of such polymers is reduced in an attempt to mitigate the undesirable effect on the viscosity of the finished composition, the reduced viscosity is obtained at the expense of anti-soiling properties.
  • the anti-soiling agents of the invention can be employed in fabric softener compositions to provide a desirable level of anti-soiling performance without at the same time causing the viscosity of the finished composition to be unacceptably high.
  • compositions of the invention will preferably contain an emulsifying agent.
  • Suitable emulsifiers which can be utilized in the compositions of the present invention include those selected from the group consisting of 1) the condensation product of one mole of alkylphenol wherein the alkyl chain contains from about 8 to about 18 carbon atoms with from about one to about 100 moles of ethylene oxide.
  • nonionics are the condensation product of one mole of nonylphenol with 9.5 moles of ethylene oxide; the condensation product of one moleof decylphenol with 40 moles of ethylene oxide; the condensation product of one mole of dodecylphenol with 35 moles of ethylene oxide; the condensation product of one mole of nonylphenol with 1.5 moles of ethylene oxide; the condensation product of one mole of tetradecylphenol with 35 moles of ethylene oxide; and the condensation product of one mole of hexadecylphenol with 30 moles of ethylene oxide; (2) the condensation product of one mole of an aliphatic alcohol wherein the alkyl chain contains from to about 24 carbon atoms with from about one to about 100 moles of ethylene oxide.
  • condensation product of one mole of coconut alkyl alcohol with 45 moles of ethylene oxide is the condensation product of one mole of tallowalkyl alcohol with 30 moles of ethylene oxide; the product sold by Union Carbide under the tradename Tergitol 15-8-9 which is the condensation product of one mole of secondary alkyl alcohol with alkyl chain lengths of from 11 to 15 with 9 moles of ethylene oxide; and the product sold by Union Carbide under the tradename Tergitol 15-S-3 which is the condensation product of one mole of secondary alkyl alcohol with alkyl chain lengths of from 1 1 to 15 with 3 moles of ethylene oxide; (3) polyethylene glycols having a molecular weight of from about 1400 to about 30,000.
  • nonionics for example, Dow Chemical Company manufactures these nonionics in molecular weights of 20,000, 9,500, 7,500, 4,500, 3,400 and 1,450. All of these nonionics are wax-like solids which melt between l00F and 200F, and (4) mixtures thereof.
  • emulsifiers function as solubilizing agents to prevent precipitation and maintain excellent freezethaw characteristics of the liquid compositions. These emulsifiers further act as stabilizers to promote shelf stability and maintain the desired viscosity.
  • the emulsifiers are present in the composition of the present invention from about 0 to about 2% by weight, preferably from about 0.25% to about 1%. If more than about 2% by weight is used no advantages are achieved and product stability problems can arise. Small amounts of emulsifier are usually necessary to achieve the desired stability and freeze-thaw characteristics while maintaining the desired viscosity of the composition.
  • Miscellaneous materials such as optical brighteners such as the anionic stilbenes, coloring agents, and other materials which are well known as constituents in fabric softener compositions and which are compatible in the compositions of the present invention can also be present in minor amounts.
  • the detergent composition used contained 8% sodium dodecyl benzene sulfonate, 9% sodium tallow alkyl sulfate, 50% sodium tripolyphosphate, 6% sodium silicate having a S10 Na O ratio of 1.6, 13% sodium sulfate, 0.6% of a condensation reaction product of coconut alcohol and an average of 6 moles of ethylene oxide, and 1.5% ammonium coconut fatty acid amide and the balance water to
  • the detergent composition was used at a product concentration of 0.1%, the wash water was at a temperature of F and contained water hardness of 7 grains.
  • the washing process lasted 10 minutes followed by a 5 minute rinse cycle with water at a temperature of l00F and containing water hardness of 7 grains.
  • a fabric softener/soil release composition embodying the present invention (identified below as COMPOSI- TlON B) was tested and results compared to those obtained with a similar composition but one which did not contain a soil release agent as required by the present invention (identified as COMPOSITION A, below).
  • COMPOSITION A and COMPOSITION B were each added to the rinse cycle of the laundering procedures described above in order to expose the washed fabric to the fabric softener/soil release composition on the one properties has the Component Parts by Weight hand (COMPOSITION B) and to the softening compo- 5 Distear I dimethyl 5 2 sition on the other (COMPOSITION A).
  • COMPOSITION B Component Parts by Weight hand
  • COMPOSITION A the y iffiyp l m concentration of fabric softener agent was 75 ppm. In 2?
  • the fabric swatches eicosyl trimethyl ammonium chloride were allowed to stand overnight for a period of 18 tetradecyl-tri(2-hydroxyethyl)ammonium methyl hours to permit the oily soil to age on the fabrics.
  • the sulfate, aged swatches were then weighed, washed, and then octadecyl-tri(2-hydroxyethyl)ammonium methyl suldried.
  • the fabrics were then reweighed and this permitfate, ted calculation of the weight percentage of oily soil di(Z-benzyloctadecyl)dimethyl ammonium ethyl sulwhich was removed during the washing step. fate,
  • ditallowalkyl dimethyl ammonium bromide ditallowalkyl dimethyl ammonium methyl sulfate, ditetradecyl diethyl ammonium chloride, ditetradecyl dimethyl ammonium chloride, coconutalkyl triethyl ammonium chloride, and
  • Example 111 Methyl Cellulose (viscosity of 50 cp at 2% in water and 20C Emulsifier (mixture of nonyl phenol ethoxylates) lsopropanol, ethanol, optical hrighteners, dye, miscellaneous Water 1.6 Balance to 100 Substantially the same results in softening are obtained with the compositions of Example 111 when any of the following emulsifiers are substituted on an equal weight basis for the nonyl phenol ethoxylate of Example Ill.
  • anti-soiling and soil-release are used interchangeably notwithstanding that there may be mechanistic differences involved.
  • a liquid fabric softener composition having a viscosity of less than about 250 centipoises and effective to provide fabrics with softening and anti-soiling prop erties consisting essentially of:
  • composition of claim 1 wherein the cationactive fabric softener compound is a quaternary ammonium softener compound having the formula wherein R is hydrogen or an aliphatic group of from 1 to 22 carbons; R is an aliphatic group having from 12 to 22 carbon atoms; R; and R are each alkyl groups of from one to 3 carbon atoms; and X is an anion selected from the group consisting of halogen, acetate, phosphate, nitrate and methyl sulfate.
  • composition of claim 1 wherein the soil re lease agent is hydroxypropyl methyl cellulose.
  • composition of claim 4 wherein the hydroxypropyl methyl cellulose has a methoxyl substitution of from 27% to 30% by weight and a propylene glycol ether substitution of from 7% to 12% by weight.
  • composition of claim 1 wherein the emulsifier ranges from 0.25% to 1% and is a mixture of secondary C alcohol ethoxylates.
  • composition of claim 1 wherein the cationic fabric softener ranges from 2.5% to about 6%.
  • composition of claim 1 wherein the soil release agent is methyl cellulose.
  • a method of imparting softening and anti-soiling properties to washed textiles which comprises treating previously-washed textiles in an aqueous rinsing bath containing minor but effective amounts of a cationactive fabric softening agent having from one to two straight chain organic groups of from 8 to 22 carbon atoms and a soil release agent selected from the group consisting of hydroxyalkyl alkyl cellulose and alkyl cellulose where each alkyl has from 1 to 3 carbon atoms, said soil release agent providing a viscosity of less than about 400 centipoises determined at a two percent by weight concentration in water at 20C.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US375218A 1973-03-23 1973-06-29 Fabric softener and soil-release composition and method Expired - Lifetime US3928213A (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
US375218A US3928213A (en) 1973-03-23 1973-06-29 Fabric softener and soil-release composition and method
CA195,104A CA1024703A (en) 1973-03-23 1974-03-15 Fabric softener and soil-release composition and method
DE2413042A DE2413042B2 (de) 1973-03-23 1974-03-19 Flüssiges Mittel zum gleichzeitigen Weich- und Schmutzabweisendmachen von Geweben und dessen Verwendung
CH406974A CH603788A5 (it) 1973-03-23 1974-03-22
IT42532/74A IT1005781B (it) 1973-03-23 1974-03-22 Composizione e metodo per imparti re a tessuti morbidezza e proprie ta di anti insudiciamento
AT239574A AT347552B (de) 1973-03-23 1974-03-22 Fluessiges textilkonditioniermittel und ver- fahren zum konditionieren gewaschener textilien
GB1283674A GB1459935A (en) 1973-03-23 1974-03-22 Fabric softener and soil-release composition and method
FR7410015A FR2222476B1 (it) 1973-03-23 1974-03-22
NL7403897A NL7403897A (it) 1973-03-23 1974-03-22
JP49033057A JPS5035495A (it) 1973-03-23 1974-03-23
BE142415A BE812785A (fr) 1973-03-23 1974-03-25 Composition et procede d'adoucissement et d'anti-salissement des etoffes
CA202,583A CA1027713A (en) 1973-03-23 1974-06-17 Fabric softener and soil-release composition and method

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US34438973A 1973-03-23 1973-03-23
US375218A US3928213A (en) 1973-03-23 1973-06-29 Fabric softener and soil-release composition and method
US42502773A 1973-12-14 1973-12-14

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US3928213A true US3928213A (en) 1975-12-23

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US (1) US3928213A (it)
JP (1) JPS5035495A (it)
AT (1) AT347552B (it)
BE (1) BE812785A (it)
CA (2) CA1024703A (it)
CH (1) CH603788A5 (it)
DE (1) DE2413042B2 (it)
FR (1) FR2222476B1 (it)
GB (1) GB1459935A (it)
IT (1) IT1005781B (it)
NL (1) NL7403897A (it)

Cited By (19)

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US4136038A (en) * 1976-02-02 1979-01-23 The Procter & Gamble Company Fabric conditioning compositions containing methyl cellulose ether
US4164392A (en) * 1977-12-22 1979-08-14 Milliken Research Corporation Textile materials having durable soil release and moisture transport characteristics and process for producing same
US4168954A (en) * 1977-12-22 1979-09-25 Milliken Research Corporation Textile materials having durable soil release and moisture transport characteristics and process for producing same
US4379059A (en) * 1980-11-07 1983-04-05 Lever Brothers Company Fabric softening composition and a process for preparing it from cationic surfactant and thickener
US4540499A (en) * 1982-07-05 1985-09-10 Lion Corporation Fabric treating composition for addition to granular detergent
US4661267A (en) * 1985-10-18 1987-04-28 The Procter & Gamble Company Fabric softener composition
US4715990A (en) * 1983-10-05 1987-12-29 Colgate-Palmolive Company Stable soil release promoting liquid detergent containing stabilized enzymes
US4751008A (en) * 1983-10-05 1988-06-14 Colgate-Palmolive Company Stable soil release promoting liquid detergent containing fabric softener and enzymes
US4956447A (en) * 1989-05-19 1990-09-11 The Procter & Gamble Company Rinse-added fabric conditioning compositions containing fabric sofening agents and cationic polyester soil release polymers and preferred cationic soil release polymers therefor
US5160641A (en) * 1985-07-29 1992-11-03 Lever Brothers Company, Division Of Conopco, Inc. Detergent composition with fabric softening properties
US5207933A (en) * 1991-08-28 1993-05-04 The Procter & Gamble Company Liquid fabric softener with insoluble particles stably suspended by soil release polymer
US5232613A (en) * 1991-08-28 1993-08-03 The Procter & Gamble Company Process for preparing protected particles of water sensitive material
US5232612A (en) * 1991-08-28 1993-08-03 The Procter & Gamble Company Solid, particulate fabric softener with protected, dryer-activated, cyclodextrin/perfume complex
US5234611A (en) * 1991-08-28 1993-08-10 The Procter & Gamble Company Fabric softener, preferably liquid, with protected, dryer-activated, cyclodextrin/perfume complex
US5236615A (en) * 1991-08-28 1993-08-17 The Procter & Gamble Company Solid, particulate detergent composition with protected, dryer-activated, water sensitive material
US5405542A (en) * 1989-05-19 1995-04-11 The Procter & Gamble Company Rinse-added fabric conditioning compositions containing fabric softening agents and cationic polyester soil release polymers and preferred cationic soil release polymers therefor
US5916864A (en) * 1996-07-24 1999-06-29 Sunstar Inc. Laundry detergent composition comprising a combination of a sparingly water soluble solvent and an easily water soluble solvent
WO2000065015A2 (en) * 1999-04-27 2000-11-02 The Procter & Gamble Company Surface care compositions and methods for treating surfaces
WO2004101724A1 (en) * 2003-05-13 2004-11-25 Unilever Plc Fabric conditioning compositions

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4128484A (en) 1975-07-14 1978-12-05 The Procter & Gamble Company Fabric softening compositions
GR67665B (it) * 1979-05-21 1981-09-02 Unilever Nv
JPS5938845B2 (ja) * 1980-09-04 1984-09-19 新日本製鐵株式会社 スラブ保温装置
US4497716A (en) * 1982-12-23 1985-02-05 Lever Brothers Company Fabric softening composition
GB8410321D0 (en) * 1984-04-19 1984-05-31 Unilever Plc Aqueous concentrated fabric softening composition
GB8410320D0 (en) * 1984-04-19 1984-05-31 Unilever Plc Aqueous fabric softening composition
US4711730A (en) * 1986-04-15 1987-12-08 The Procter & Gamble Company Capped 1,2-propylene terephthalate-polyoxyethylene terephthalate polyesters useful as soil release agents
GB8804818D0 (en) * 1988-03-01 1988-03-30 Unilever Plc Fabric softening composition
JP2791845B2 (ja) * 1992-02-10 1998-08-27 東京コパル化学 株式会社 除電機能材料及びその製造方法
GB9208405D0 (en) * 1992-04-16 1992-06-03 Unilever Plc Fabric conditioning composition
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US4136038A (en) * 1976-02-02 1979-01-23 The Procter & Gamble Company Fabric conditioning compositions containing methyl cellulose ether
US4164392A (en) * 1977-12-22 1979-08-14 Milliken Research Corporation Textile materials having durable soil release and moisture transport characteristics and process for producing same
US4168954A (en) * 1977-12-22 1979-09-25 Milliken Research Corporation Textile materials having durable soil release and moisture transport characteristics and process for producing same
US4379059A (en) * 1980-11-07 1983-04-05 Lever Brothers Company Fabric softening composition and a process for preparing it from cationic surfactant and thickener
US4540499A (en) * 1982-07-05 1985-09-10 Lion Corporation Fabric treating composition for addition to granular detergent
US4751008A (en) * 1983-10-05 1988-06-14 Colgate-Palmolive Company Stable soil release promoting liquid detergent containing fabric softener and enzymes
US4715990A (en) * 1983-10-05 1987-12-29 Colgate-Palmolive Company Stable soil release promoting liquid detergent containing stabilized enzymes
US5540850A (en) * 1985-07-29 1996-07-30 Lever Brothers Company, Division Of Conopco, Inc. Detergent composition with fabric softening properties
US5160641A (en) * 1985-07-29 1992-11-03 Lever Brothers Company, Division Of Conopco, Inc. Detergent composition with fabric softening properties
EP0220156A2 (en) * 1985-10-18 1987-04-29 The Procter & Gamble Company Fabric softener composition
EP0220156A3 (en) * 1985-10-18 1987-11-25 The Procter & Gamble Company Fabric softener composition
US4661267A (en) * 1985-10-18 1987-04-28 The Procter & Gamble Company Fabric softener composition
US4956447A (en) * 1989-05-19 1990-09-11 The Procter & Gamble Company Rinse-added fabric conditioning compositions containing fabric sofening agents and cationic polyester soil release polymers and preferred cationic soil release polymers therefor
US5405542A (en) * 1989-05-19 1995-04-11 The Procter & Gamble Company Rinse-added fabric conditioning compositions containing fabric softening agents and cationic polyester soil release polymers and preferred cationic soil release polymers therefor
US5236615A (en) * 1991-08-28 1993-08-17 The Procter & Gamble Company Solid, particulate detergent composition with protected, dryer-activated, water sensitive material
US5234611A (en) * 1991-08-28 1993-08-10 The Procter & Gamble Company Fabric softener, preferably liquid, with protected, dryer-activated, cyclodextrin/perfume complex
US5232612A (en) * 1991-08-28 1993-08-03 The Procter & Gamble Company Solid, particulate fabric softener with protected, dryer-activated, cyclodextrin/perfume complex
US5232613A (en) * 1991-08-28 1993-08-03 The Procter & Gamble Company Process for preparing protected particles of water sensitive material
US5207933A (en) * 1991-08-28 1993-05-04 The Procter & Gamble Company Liquid fabric softener with insoluble particles stably suspended by soil release polymer
US5916864A (en) * 1996-07-24 1999-06-29 Sunstar Inc. Laundry detergent composition comprising a combination of a sparingly water soluble solvent and an easily water soluble solvent
WO2000065015A2 (en) * 1999-04-27 2000-11-02 The Procter & Gamble Company Surface care compositions and methods for treating surfaces
WO2000065015A3 (en) * 1999-04-27 2001-02-08 Procter & Gamble Surface care compositions and methods for treating surfaces
WO2004101724A1 (en) * 2003-05-13 2004-11-25 Unilever Plc Fabric conditioning compositions
US20080176784A1 (en) * 2003-05-13 2008-07-24 Ann Clowes Fabric Conditioning Compositions

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ATA239574A (de) 1978-05-15
CA1027713A (en) 1978-03-14
BE812785A (fr) 1974-09-25
IT1005781B (it) 1976-09-30
AT347552B (de) 1979-01-10
FR2222476A1 (it) 1974-10-18
CH603788A5 (it) 1978-08-31
DE2413042B2 (de) 1980-09-18
CA1024703A (en) 1978-01-24
GB1459935A (en) 1976-12-31
JPS5035495A (it) 1975-04-04
FR2222476B1 (it) 1978-01-06
DE2413042A1 (de) 1974-10-10
NL7403897A (it) 1974-09-25

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