US3920565A - Fabric softener composition and method - Google Patents

Fabric softener composition and method Download PDF

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Publication number
US3920565A
US3920565A US335194A US33519473A US3920565A US 3920565 A US3920565 A US 3920565A US 335194 A US335194 A US 335194A US 33519473 A US33519473 A US 33519473A US 3920565 A US3920565 A US 3920565A
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United States
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composition
carbon atoms
soap
soaps
mixture
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Expired - Lifetime
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US335194A
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English (en)
Inventor
David Russell Morton
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Procter and Gamble Co
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Procter and Gamble Co
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Priority to US335194A priority Critical patent/US3920565A/en
Priority to DE2407708A priority patent/DE2407708C2/de
Priority to IT48517/74A priority patent/IT1008886B/it
Priority to NLAANVRAGE7402367,A priority patent/NL189473C/xx
Priority to GB807474A priority patent/GB1456913A/en
Priority to FR7406221A priority patent/FR2219270B1/fr
Priority to CA193,206A priority patent/CA1110015A/en
Priority to BE141271A priority patent/BE811441A/xx
Application granted granted Critical
Publication of US3920565A publication Critical patent/US3920565A/en
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Expired - Lifetime legal-status Critical Current

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Classifications

    • 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
    • C11D3/16Organic compounds
    • C11D3/37Polymers
    • C11D3/3703Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3707Polyethers, e.g. polyalkyleneoxides
    • 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
    • C11D10/00Compositions of detergents, not provided for by one single preceding group
    • C11D10/04Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
    • C11D10/047Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap based on cationic surface-active compounds and soap
    • 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
    • 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
    • D06M13/47Compounds containing quaternary nitrogen atoms derived from heterocyclic compounds
    • D06M13/473Compounds containing quaternary nitrogen atoms derived from heterocyclic compounds having five-membered heterocyclic rings
    • 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
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/62Quaternary ammonium compounds

Definitions

  • This invention relates to fabric softener compositions AND - and to a method of softening textile materials. More particularly, it relates to fabric softening compositions having resistance to the adverse effects of anionic detergent materials and adapted to use in the repetitious but generally discontinuous laundering process which involves soiling, laundering, rinsing, soiling, etc.
  • Another object of the invention is to provide fabric softener compositions effective to impart softness to fabrics in the presence of anionic compounds encountered in laundry rinsing operations.
  • the present invention is based in part upon the discovery that fabrics can be improved in feel by treating the fabrics in an aqueousrinsing bath containing residual anionic materials and a fabric softener composition comprising a cationic fabric softener compound and a I min'oramount of a fatty soap of'from 16 to 22 carbon atoms. in its composition apect, the present invention provides an aqueous fabric softener composition consis'ting. essentially of: v r
  • the present invention provides a method of imparting softening properties to washed textiles which comprises treating previously-washed textiles in an aqueous rinsing bath containing minor amounts of anionic compounds from said previous washing and an .amount effective to soften the fabrics of a composition hereinbefore defined.
  • the fabric softening compositions of this invention provide softening properties to treated textiles notwithstanding the presenceof residual anionic compounds carried over into the rinse from 'a previous detergent wash. At low levels of softener agent usage, the presence of soap permits an improved level of fabric softening which could be obtained from the same composition free of the soap component or from a compositioncontaining additional softener agent in place of the soap.
  • 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.
  • Preferred cation-active softener compounds include the quaternary ammonium softener compounds corresponding to the formula wherein R is hydrogen or an aliphatic group of from 12 to 22 carbons; R is an aliphatic group having from 12 to 22 carbon atoms; R and R are each alkyl groups of from I to 3 carbon atoms; and X is an anion selected from halogen, acetate phosphate, nitrite and methyl sulfate radicals.
  • preferred cationic softener compounds of the invention are the dialkyl 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 l6 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 d'ipropyl ammonium phosphate; ditallow dimethyl ammonium nitrite; di(coconutalk
  • Anjespecially preferred class of quaternary ammonium softeners of the invention correspond to the formula wherein R.and R, are each straight chain aliphatic groups of from l2 to 22 carbon atoms and X is halogen, e.g., chloride. Especially preferred are ditallow dimethyl ammonium chloride and di(hydrogenated tallow-alkyl) dimethyl ammonium chloride and di(- coconut-alkyl) dimethyl ammonium chloride. these compounds being preferred from the standpoint of excellent softening properties and ready availability.
  • Suitable cation-active amine softener compounds are the primary. secondary and tertiary amine compounds having at least one straight-chain organic group of from 12 to 22'carbon atoms and l ,3-propylene diamine compounds having a straight-chain organic group of from 12m 22 carbon atoms.
  • softener actives include primary tallow amine; primary hydrogenated-tallow amine; tallow 1,3-propylene diamine; oleyl 1,3-propylene diamine; coconut l,3-propylene 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 atoms,
  • R is an alkyl containing from 1 to 4, preferably from 1 to 2, carbon atoms.
  • R is an alkyl containing from I 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 containingfrom 8 to 22, preferably at least 15, carbon atoms
  • X is an anion, preferably methyl sulfate or chloride ions.
  • 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 betoo 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 washing solution is from about 25 ppm to abou t I00 ppm.
  • the preferred range of cationic fabric softener is from about 2.5% to about 6% by weight of the total composition.
  • the alkali metal soap component suitable for use in the compositions of the present invention include the sodium and potassium soaps of higher fatty acids of from 16 to 22 carbon atoms or mixtures thereof. These soaps can be incorporated into an aqueous cationic fabric softening composition with the provision of a composition which still effectively softens fabrics in a laundry rinsing cycle containing residual anionics. Whereas such soaps can be compatibly combined with cationic softeners, soaps of fatty acids having less than 16 carbon atoms tend to mitigate the fabric-softening effects of the cationic softener.
  • Commercial soaps are generally based upon mixtures of fatty acid compounds obtained from natural sources such as tallow, coconut oil, palm kernel oil or babassu kernel oil; other commercial soaps are synthetically manufactured to simulate the fatty acids from natural materials such as tallow. Soaps from any of these commercial sources can be suitably employed so long as they contain or are altered or modified to contain at least 50%, and preferably at least by weight of fatty acids having from 16 to 22 carbon atoms.
  • tallow soaps which include the sodium or potassium salts of the mixtures of fatty acids derived from tallow can be suitably employed.
  • Tallow soaps predominate in C /C fractions and can be suitably employed in a cationic-containing fabric-softening composition.
  • coconut soaps which predominate in ⁇ In/C fractions, mitigate the softening effects, for example, of
  • fatty acid soaps derived from mixtures of natural fatty acid sources can be employed, where desired, so long as the resulting soap mixtures predominate in soaps of C or higher fatty acids as described hereinbefore.
  • a preferred soapmixture is a tallow/coconut soap blend of proportion 90: 10. This mixture is preferred from the standpoints of providing desirably optimum performance and aesthetic characteristics.
  • tallow refers to a mixture of soaps having an approximate chain-length distribution of; 2% C 32% C rand 66%
  • coconut as used herein in connection with soap or free fatty acid mixtures refers to materials having an approximate carbon chain length distribution of: 8% C 7% C 48% C 17% C 9% C 11%
  • the amount of alkali metal soap employed to provide effective resistance of the softener to the adverse effects of anionic substances will depend on such factors as the particular softening agent employed,the kind of soap, the nature of the anionic substance and the desired viscosity or physical appearance, As little as 0.5% of the soap bascd on the weight of composition may be enough in some instance, whereas up to about 4% of the soap may-be required in others.
  • the relative proportions of the cation-active fabric softener compound and soap will be based more on physical stability considerations than on performance considerations. While amounts of fabric softener and soap components within the ranges hercinbefore defined will permit the preparation of softening compositions having resistance to the residual anionics in a rinsing operation, certain ratios will be preferred to assure that the hydrophilic/- lipophilic balance allows for the provision of a composition of stable physical form. Thus, compositions containing, for example, distearyl dimethyl ammonium chloride and alkali metal 90/10 tallow/coconut soaps, respectively, in relative weight proportions of about 1 :1 or about 5:1 are preferred. These compositions are uniform in appearance and do not separate into discrete phases. Fabric softening effects are observed notwithstanding the admixture of both cationic and anionic substances. The percentages of fabric softener and soap may be adjusted within the above defined limits to suit the requirements of each case andto combine softening and stability effects.
  • compositions of the invention can be formulated in a convenient manner by admixture of the softener and soap components and addition to water.
  • a preferred method of preparing the compositions involves the preparation of an aqueous soap solution and addition to an aqueous dispersion of the softening agent. It
  • mixed micelle may be'formed whenthc anionic substance is a higher fatty soap as hereinbefore described.
  • compositions of the invention rather than having than is obtained where one fluid ounce of fabric softener having'5% of the-quaternary compound'is employed.
  • the same softening contribution is not observed with higher usage levels, e.g. two fluid ounces. in which case the compositions of the invention will have their greater attraction to users whocustomarily or ha-- bitually employ low levels of softening composition in laundering operations.
  • the compositions of the invention are additionally characterized by a pearlescent appea'rance which may be attractive to users of fabricsoftening compositions.
  • compositions of the invention will preferably contain an emulsifying agent. Suitableemulsifiers which can be utilized in the compositions of the present.
  • the condensation product of 1 mole of alkylphenol wherein the alkyl chain contains from about 8 to about 18 carbon atoms with from about 1 to about moles of ethylene oxide include those selected from the group consisting of 1 the condensation product of 1 mole of alkylphenol wherein the alkyl chain contains from about 8 to about 18 carbon atoms with from about 1 to about moles of ethylene oxide.
  • these nonionics are the condensation product of 1 mole of nonylphenol with 9.5 moles of ethylene oxide; the condensation product of 1 mole of decylphenol with 40 moles of ethylene oxide; the condensation product of 1 mole of dodecylphenol with 35 moles of ethylene oxide; the condensation product of 1 mole of nonylphenol with 1.5 moles of ethylene oxide; the condensation product of 1 mole of tetradecylphenol with 35 moles of ethylene oxide; and the condensation product of 1 mole of hexadecylphenol with 30 moles of ethylene oxide; (2) the condensation product of 1 mole of an
  • condensation product of 1 mole of coconut alkyl alcohol with 45 moles of ethylene oxide is the condensation product of 1 mole of tallow-alkyl 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 1 mole of secondary alkyl alcohol with alkyl chain lengths of from 1 l to 15 with 9 moles of ethylene oxide
  • the product sold by Union Carbide under the tradename "Tergitol 15-8-37” which is the condensation product of 1 mole of secondary alkyl alcohol with alkyl chain lengths of from 1 1 to 15 with 3 moles of ethylene oxide
  • 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 100 and 200F, and (4) mixtures thereof.
  • emulsifiers function as solubilizing agents to prevent precipitation and maintain excellent freezethaw characteristics of the liquid compositions. These emulsifier s 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. perfumes. and other materials which are well known as constituents in fabric softener compositions and which are compatible in the compositions of the presnt invention can also be present in minor amounts.
  • composition was characterized by a pearleseent appearance upon cooling and was physically stable, i.e. did not separate upon standing.
  • Example I The composition of Example I was used as follows: Five terry wash cloths were washed in a miniature-size,
  • Example I top loading washing machine containing 1 /2 gals. of water having a temperature of 130F, and a hardness of 7 grains. using 6.1 grams of a commercially-available anionic-based laundry detergent. The washing process lasted ten minutes. The cloths were then rinsed using l'/2 gals. of F. water and 2.6 cc. or 5.2 cc. of the composition of Example I (corresponding, respec tively, to l or 2 fluid ounces in 17 gal. of water). This cycle of washing and rinsing was then repeated. The composition of Example I gave noticeable softening effects at levels of l and 2 ounces on the terry wash cloths. Whereas. the commercially-available softener composition described hereinbefore provided a greater softening effect at the two-ounce level than the composition of Example I, the composition of Example I provided a greater effect at the 1 ounce level.
  • Example I Substantially the same results in softening are obtained with the composition of Example I when any of the following cationic fabric softeners is substituted on an equal weight basis for the ditallow dimethyl ammonium chloride in Example I, (coconut as used below has the following chain length distribution: 2% C 66% C 23% C and 9% C ditallowalkyl dimethyl ammonium chloride,
  • Example I ditetradecyl diethyl ammonium chloride, ditetradecyl dimethyl ammonium chloride, coconutalkyl triethyl ammonium chloride, and dicoconutalkyl diethyl ammonium chloride- Substantially the same results in softening are obtained with the compositions of Example I when any of the following emulsifiers are substituted on an equal weight basis for the n onyl phenol ethoxylate of Example l.
  • the fabric softener composition thus formulated was stable. When tested according to the procedure of Example the clothes utilized were soft to the touch.
  • a fabric softener composition is prepared according to the procedure of Example I and contains the following ingredients:
  • a liquid softener composition consisting essentially of A. from about 2 to about 15% by weight of a cationactive fabric softener compound having two straight-chain organic groups of from 8 to 22 carbon atoms;
  • emulsifier selected from the group consisting of l. the condensation product of 1 mole of alkylphenol wherein the alkyl chain contains from about 8 to about 18 carbon atoms with from about 1 to about 100 moles of ethylene oxide,
  • polyethylene glycol having a molecular weight of from about 1400 to about 30,000
  • composition of claim 1 wherein the cationicactive fabric softener compound is a quaternary ammonium softener compound having the formula wherein R is an aliphatic group of from 12 to 22 carbons; R is an aliphatic group having from 12 to 22 carbon atoms; R and R are each alkyl groups of from 1 to 3 carbon atoms; and X is ananion selected from the group consisting of halogen, acetate, phosphate, nitrite and methylsulfate.
  • composition of claim 1 wherein the soap is a mixture of alkali metal soaps, at least 50% of such soaps having from 16 to 22 carbon atoms.
  • composition of claim 1 wherein the soap is a mixture of alkali metal tallow and coconut soaps. the ratio of tallow to coconut soaps being from :5 t 50:50.
  • composition of claim 1 wherein the soap is tallow soap.
  • composition of claim 1 wherein the emulsifier ranges from 0.25% to 1% and is a mixture of nonylphenol ethoxylates.
  • composition of claim 5 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%.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Detergent Compositions (AREA)
US335194A 1973-02-23 1973-02-23 Fabric softener composition and method Expired - Lifetime US3920565A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
US335194A US3920565A (en) 1973-02-23 1973-02-23 Fabric softener composition and method
DE2407708A DE2407708C2 (de) 1973-02-23 1974-02-18 Wäßriges Textilweichmachungsmittel zur Anwendung in Spülbädern von Waschvorgängen
IT48517/74A IT1008886B (it) 1973-02-23 1974-02-20 Composizione ammorbidente i tessuti e metodo di suo impiego
NLAANVRAGE7402367,A NL189473C (nl) 1973-02-23 1974-02-21 Werkwijze voor het bereiden van een textielverzachtingsmiddel.
GB807474A GB1456913A (en) 1973-02-23 1974-02-22 Fabric softener compositiion and method
FR7406221A FR2219270B1 (it) 1973-02-23 1974-02-22
CA193,206A CA1110015A (en) 1973-02-23 1974-02-22 Fabric softener composition and method
BE141271A BE811441A (fr) 1973-02-23 1974-02-22 Compositions adoucissantes pour tissus et application

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US335194A US3920565A (en) 1973-02-23 1973-02-23 Fabric softener composition and method

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US3920565A true US3920565A (en) 1975-11-18

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US (1) US3920565A (it)
BE (1) BE811441A (it)
CA (1) CA1110015A (it)
DE (1) DE2407708C2 (it)
FR (1) FR2219270B1 (it)
GB (1) GB1456913A (it)
IT (1) IT1008886B (it)
NL (1) NL189473C (it)

Cited By (27)

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US4045361A (en) * 1975-05-21 1977-08-30 The Procter & Gamble Company Fabric conditioning compositions
JPS5352799A (en) * 1976-10-19 1978-05-13 Kao Corp Fabric softening agent composition
US4140641A (en) * 1978-03-17 1979-02-20 Colgate-Palmolive Company Concentrated liquid detergent with fabric softener
US4173539A (en) * 1977-10-31 1979-11-06 Lever Brothers Company Cationic surfactant compositions
JPS55119000A (en) * 1979-03-06 1980-09-12 Lion Fat Oil Co Ltd Leather and feather treating composition
US4230590A (en) * 1978-12-11 1980-10-28 Colgate Palmolive Company Detergent softener compositions containing a soap-cellulose ether mixture
US4265772A (en) * 1978-11-16 1981-05-05 The Procter & Gamble Company Antistatic, fabric-softening detergent additive
US4292035A (en) * 1978-11-13 1981-09-29 The Procter & Gamble Company Fabric softening compositions
US4298480A (en) * 1978-12-11 1981-11-03 Colgate Palmolive Co. Detergent softener compositions
US4308024A (en) * 1978-11-03 1981-12-29 Lever Brothers Company Fabric softening composition
US4326971A (en) * 1978-12-11 1982-04-27 Colgate Palmolive Company Detergent softener compositions
US4329237A (en) * 1979-11-21 1982-05-11 Colgate-Palmolive Company Detergent softener compositions
US4411803A (en) * 1980-10-27 1983-10-25 Colgate Palmolive Company Detergent softener compositions
DE3309569A1 (de) * 1982-03-22 1983-10-27 Colgate-Palmolive Co., 10022 New York, N.Y. Konzentrierte waescheweichspuelmittel
FR2528864A1 (fr) * 1982-06-22 1983-12-23 Colgate Palmolive Co Compositions assouplissantes concentrees pour textiles et leurs procedes de fabrication
US4427558A (en) 1981-05-08 1984-01-24 Lever Brothers Company Fabric conditioning materials
US4439331A (en) * 1981-09-04 1984-03-27 Hoechst Aktiengesellschaft Textile softener
US4439330A (en) * 1981-01-16 1984-03-27 The Procter & Gamble Company Textile treatment compositions
US4450085A (en) * 1981-05-01 1984-05-22 Colgate Palmolive Company Detergent softener compositions
US4460485A (en) * 1983-07-15 1984-07-17 Lever Brothers Company Polyester fabric conditioning and whitening composition
US4661270A (en) * 1983-05-11 1987-04-28 Colgate-Palmolive Company Concentrated fabric softening composition and methods for making same
US4678590A (en) * 1984-10-25 1987-07-07 Lion Corporation Softener composition
US5160641A (en) * 1985-07-29 1992-11-03 Lever Brothers Company, Division Of Conopco, Inc. Detergent composition with fabric softening properties
US5411674A (en) * 1989-10-06 1995-05-02 Kao Corporation Detergent composition having a sulfosuccinic amide
US5696174A (en) * 1995-02-14 1997-12-09 Allied Foam Tech Corporation Stable and water-resistant aqueous foam composition
US20040107504A1 (en) * 2002-12-05 2004-06-10 Blangiforti Anna Carner Leather therapy treatment
US20050164905A1 (en) * 2004-01-16 2005-07-28 Nalini Chawla Aqueous laundry detergent compositions having improved softening properties and improved aesthetics

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US3958059A (en) * 1973-10-01 1976-05-18 The Procter & Gamble Company Fabric treatment composition
US4446032A (en) * 1981-08-20 1984-05-01 International Flavors & Fragrances Inc. Liquid or solid fabric softener composition comprising microencapsulated fragrance suspension and process for preparing same
US4464271A (en) * 1981-08-20 1984-08-07 International Flavors & Fragrances Inc. Liquid or solid fabric softener composition comprising microencapsulated fragrance suspension and process for preparing same
US4497716A (en) * 1982-12-23 1985-02-05 Lever Brothers Company Fabric softening composition

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US3686025A (en) * 1968-12-30 1972-08-22 Procter & Gamble Textile softening agents impregnated into absorbent materials
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Cited By (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4045361A (en) * 1975-05-21 1977-08-30 The Procter & Gamble Company Fabric conditioning compositions
JPS5352799A (en) * 1976-10-19 1978-05-13 Kao Corp Fabric softening agent composition
US4144177A (en) * 1976-10-19 1979-03-13 Kao Soap Co., Ltd. Softener composition for fabrics
JPS569997B2 (it) * 1976-10-19 1981-03-05
US4173539A (en) * 1977-10-31 1979-11-06 Lever Brothers Company Cationic surfactant compositions
US4140641A (en) * 1978-03-17 1979-02-20 Colgate-Palmolive Company Concentrated liquid detergent with fabric softener
USRE34062E (en) * 1978-11-03 1992-09-15 Lever Brothers Company Fabric softening composition contains water-insoluble surfactant and aliphatic mono-carboxylic acid
US4308024A (en) * 1978-11-03 1981-12-29 Lever Brothers Company Fabric softening composition
US4292035A (en) * 1978-11-13 1981-09-29 The Procter & Gamble Company Fabric softening compositions
US4265772A (en) * 1978-11-16 1981-05-05 The Procter & Gamble Company Antistatic, fabric-softening detergent additive
US4298480A (en) * 1978-12-11 1981-11-03 Colgate Palmolive Co. Detergent softener compositions
US4230590A (en) * 1978-12-11 1980-10-28 Colgate Palmolive Company Detergent softener compositions containing a soap-cellulose ether mixture
US4326971A (en) * 1978-12-11 1982-04-27 Colgate Palmolive Company Detergent softener compositions
JPS55119000A (en) * 1979-03-06 1980-09-12 Lion Fat Oil Co Ltd Leather and feather treating composition
JPS6127440B2 (it) * 1979-03-06 1986-06-25 Lion Corp
US4329237A (en) * 1979-11-21 1982-05-11 Colgate-Palmolive Company Detergent softener compositions
US4411803A (en) * 1980-10-27 1983-10-25 Colgate Palmolive Company Detergent softener compositions
US4439330A (en) * 1981-01-16 1984-03-27 The Procter & Gamble Company Textile treatment compositions
US4476031A (en) * 1981-01-16 1984-10-09 The Procter & Gamble Company Textile treatment compositions
US4450085A (en) * 1981-05-01 1984-05-22 Colgate Palmolive Company Detergent softener compositions
US4427558A (en) 1981-05-08 1984-01-24 Lever Brothers Company Fabric conditioning materials
US4439331A (en) * 1981-09-04 1984-03-27 Hoechst Aktiengesellschaft Textile softener
DE3309569A1 (de) * 1982-03-22 1983-10-27 Colgate-Palmolive Co., 10022 New York, N.Y. Konzentrierte waescheweichspuelmittel
FR2528864A1 (fr) * 1982-06-22 1983-12-23 Colgate Palmolive Co Compositions assouplissantes concentrees pour textiles et leurs procedes de fabrication
US4661270A (en) * 1983-05-11 1987-04-28 Colgate-Palmolive Company Concentrated fabric softening composition and methods for making same
US4460485A (en) * 1983-07-15 1984-07-17 Lever Brothers Company Polyester fabric conditioning and whitening composition
US4678590A (en) * 1984-10-25 1987-07-07 Lion Corporation Softener composition
US5160641A (en) * 1985-07-29 1992-11-03 Lever Brothers Company, Division Of Conopco, Inc. Detergent composition with fabric softening properties
US5540850A (en) * 1985-07-29 1996-07-30 Lever Brothers Company, Division Of Conopco, Inc. Detergent composition with fabric softening properties
US5411674A (en) * 1989-10-06 1995-05-02 Kao Corporation Detergent composition having a sulfosuccinic amide
US5696174A (en) * 1995-02-14 1997-12-09 Allied Foam Tech Corporation Stable and water-resistant aqueous foam composition
US20040107504A1 (en) * 2002-12-05 2004-06-10 Blangiforti Anna Carner Leather therapy treatment
US6797011B2 (en) * 2002-12-05 2004-09-28 Anna Carner Blangiforti Leather therapy treatment
US20050164905A1 (en) * 2004-01-16 2005-07-28 Nalini Chawla Aqueous laundry detergent compositions having improved softening properties and improved aesthetics

Also Published As

Publication number Publication date
FR2219270B1 (it) 1978-11-10
DE2407708A1 (de) 1974-08-29
FR2219270A1 (it) 1974-09-20
NL189473C (nl) 1993-04-16
IT1008886B (it) 1976-11-30
NL7402367A (it) 1974-08-27
CA1110015A (en) 1981-10-06
NL189473B (nl) 1992-11-16
BE811441A (fr) 1974-08-22
DE2407708C2 (de) 1987-11-12
GB1456913A (en) 1976-12-01

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