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US3578591A - Fabric softener composition - Google Patents

Fabric softener composition Download PDF

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Publication number
US3578591A
US3578591A US682592A US3578591DA US3578591A US 3578591 A US3578591 A US 3578591A US 682592 A US682592 A US 682592A US 3578591D A US3578591D A US 3578591DA US 3578591 A US3578591 A US 3578591A
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Prior art keywords
fabric
sodium
alkyl
sulfolene
composition
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Expired - Lifetime
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US682592A
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English (en)
Inventor
Christina Nicholson Lazaridis
Harold Eugene Wixon
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Colgate Palmolive Co
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Colgate Palmolive Co
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/144—Alcohols; Metal alcoholates
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/349—Organic compounds containing sulfur additionally containing nitrogen atoms, e.g. nitro, nitroso, amino, imino, nitrilo, nitrile groups containing compounds or their derivatives or thio urea
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
    • D06M13/248—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/3481—Organic compounds containing sulfur containing sulfur in a heterocyclic ring, e.g. sultones or sulfolanes

Definitions

  • the present invention relates to a non-yellowing fabricsoftening composition which may be used in conjunction with other conventional laundering additives.
  • finishing Among the desirable properties that may be provided by finishing are enhanced softness, antistatic activity, wrinkle resistance, stiffness or firmness, shape retention, rot resistance and the like.
  • the particular end use of the fabric generally governs the nature of the property modifications provided by mill finishing. It is not generally feasible to effect all property modifications on a single fabric. Moreover, there are many fabrics that are not subjected to mill finishing at all. Therefore, there are many fabrics and garments made therefrom in the hands of con sumers that would have enhanced value with certain prop erty modifications.
  • a cationic substance such as the aforementioned softeners
  • anionic detergent materials results in a precipitate which is completely ineffective as a fabric softener.
  • This manifestation of incompatibility is also un- Patented May 11, 1971 desirable because it removes detergent from the wash cycle and therefore requires more to accomplish the necessary and desired washing efiiciency.
  • a further disadvantage of the cationic fabric softeners is that many of them are waxy or gummy in nature making them diflicult to weigh or measure, to mix or disperse with other textile-treating agents, and to place them in a form which may be readily applied to textiles.
  • a still further object of the instant invention is to provide a non-yellowing fabric-softening composition.
  • Still another object of the instant invention is to provide a non-yellowing fabric-softening composition which is compatible with and useful in conjunction with anionc, catonic, and nonionic detergent compositions.
  • Another object of the instant invention is to provide a fabric-softening composition comprising 3-sulfolene or its derivatives in a combination with a long-chain aliphatic alcohol.
  • a further object of the instant invention is to provide a non-yellowing fabric softening composition comprising 3-sulfolene and its derivatives and l-hexadecanol alcohol.
  • a still further object of the instant invention is to provide a non-yellowing fabric softening composition comprising 3-sulfolene and l-hexadecanol alcohol in combination with a detergent.
  • the fabric-softening composition ofthe instant invention comprises a mixture of 3-sulfolene or substituted 3-sulfolene derivatives in combination with long-chain aliphatic alcohols.
  • the 3-sulfolene and its derivatives which are useful in the instant invention include 3-sulfoluene and'its alkyl, alkoxy, alkylalkoxy, acyl, carboalkoxy, carboxamido, sulfonamido and halogen derivatives.
  • the useful derivatives include the: methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, secondary-butyl, tertiary-butyl, n-amyl, iso-amyl, tertiary-amyl, and other isomeric amyls, n-hexyl, iso-hexyl, and other isomeric hexyls, hydroxy, methoxy, ethoxy, propoxy, methylmethoxy, ethylmethoxy, propylmethoxy, butylmethoxy, pentylmethoxy, hexylmethoxy, octylmethoxy, decylmethoxy, dodecylmethoxy, tetradecylmethoxy, hexadecylmethoxy, octadecylmethoxy;
  • the long-chain alcohols useful in the instant invention 1 include saturated aliphatic alcohols having from 16 to 22 carbon atoms.
  • the useful alcohols include straight and branched chain alcohols, including: decanol, undecanol, lauryl alcohol, tridecanol, tetradecanol, myristyl alcohol, pentadecanol hexadecanol, cetyl alcohol, heptadecanol, octadecanol, stearyl alcohol, nondecanol, eicosanol, heneicosanol, docosanol.
  • Some additional alcohols useful in connection with the instant invention include: isodecanol, isotetradecanol, isohexadecanol, isooctadecanol, and the position isomers of all the above alcohols, e.g., l-hexadecanol, 3-hexadecanol, S-hexadecanol, 6-hexadecanol, 8-hexadecanol.
  • EXAMPLE 1 The softening ability of cetyl alcohol for cloth was demonstrated in a test in which cetyl alcohol was dissolved in hot water and a terry cloth towel was treated therewith. The terry cloth towel was then rinsed, air dried, and subsequently tested for its degree of softness. The towel received a rating of 1 on a scale of 10 with a rating of 10 being considered excellent insofar as softness and flufiiness are concerned and a rating of 1 indicating no noticeable change. A rating of 5 cannot generally be distinguished by the layman from a rating of 1.
  • EXAMPLE 2 3-sulfolene was tested according to the method of Example l.
  • the terry cloth towel was given a softness rating of 1.
  • EXAMPLE 3 A mechanical blend consisting of one part of 3-sulfolene to ten parts of alcohol was tested according to the method of Example 1. A terry cloth towel was given a softness rating of 8. The relative amounts of each ingredi ent of the test compositions were varied so that a composition containing one part of 3-sulfolene to one, three, five, and eight parts of cetyl alcohol; and two parts of cetyl alcohol to three, five, seven, nine, and fifteen parts of 3-sulfolene were also tested. Each of these composi .tions produced a satisfactory result.
  • Percent Fabric softener two parts of 3-sulfolene and three' parts of l-hexadecanol 0.01 Linear alkylbenzene sulfonate 0.02 Sodium tripolyphosphate 0.06
  • the blend of fabric softener was dissolved in hot water to which was added the linear alkylbenzene sulfonate. This aqueous solution was then added to a washing machine along with sodium tripolyphosphate. A terry cloth tower was then Washed with this composition through the normal washing machine sequence of wash cycle, spin cycle, rinse cycle, and spin cycle. The terry cloth towel was then air-dried and rated for its relative degree of softness, receiving a rating of 8.
  • a rinse cycle fabric softening composition is prepared having the following components:
  • Fabric softening composition compounds of the instant invention may be employed either alone or in direct combination with conventional detergents.
  • the useful detergents which may be used in conjunction with the instant fabric softening composition include anionic detergents such as alkylbenzene-sulfonic acid and its salts, and compounds of the formula alkyl-phenyl-SOg-M wherein alkyl is an alkyl radical of a fatty acid and M is hydrogen or an alkali metal, which compounds comprise a well-known class of anionic detergents and include sodium dodecylbenzene sulfonate, potassium dodecylbenzenesulfonate, sodium laurylbenzenesulfonate, sodium cetylbenzenesulfonate.
  • alkali metal salts of the higher alkylsulfonic acids and the alkali metal dialkyl sulfosuccinates e.g., sodium dioctylsulfoscuccinate, and sodium dihexylsulfosuccinate, sodium sulfoethylphthalate, sodium lauryl-p-anisidinesulfonate; sodium tetradecanesulfonate; sodium diisopropyhlaphthalenesulfonate; sodium octylphenoxyethoxyethylsulfonate, etc.; and the alkali metal alkyl sulfates, e.g., sodium lauryl sulfate.
  • alkylbenzene-sulfonic acid and salts thereof there are included those which are biodegradable and which are particularly characterized by a linear alkyl substituent of from C to C and preferably from C to C It is, of course, understood that the carbon chain length represents, in general, an average chain length since the method for producing such products usually employ alkylating reagents of mixed chain length.
  • substantially pure olefins as well as alkylating compounds used in other techniques can and do give alkylated benzene sulfonates wherein the alkyl moiety is substantially (ie at least 99%) of one chain length, i.e., C12, C C 01' C
  • the linear alkyl benzene sulfonates are further characterized by the position of the benzene ring in the linear alkyl chain, with any of the position isomers (i.e., alpha to omega) being operable and contemplated.
  • the linear alkyl benzene sulfonates are generally and conveniently prepared by sulfonating the corresponding alkyl benzene hydrocarbons which in turn may be prepared by alkylating benzene with a linear alkyl halide, a l-alkene or a linear primary or secondary alcohol.
  • Pure isomers (of the l-phenyl isomer) are prepared by reduction of the acylated benzene (alkyl phenyl ketone) using a modification of the WolfE-Kishner reaction.
  • the 2-phenyl isomer is obtained from n-undecyl phenyl ketone and methyl magnesium bromide to form the tertiary alcohol which is dehydrated to the alkene and then hydrogenated.
  • the S-phenyl isomer is obtained similarly from n-heptyl phenyl ketone and n-butyl magnesium bromide.
  • the other isomers are obtained in a similar manner from the appropriate n-alkyl phenyl ketone and n-alkyl magnesium bromide.
  • benzene sulfonates may also ernploy the lower alkyl (C to C analogs of benzene such as toluene, xylene, the trimethyl benzenes, ethylbenzene, isopropyl benzene and the like.
  • the sulfonates are generally employed in the water soluble salt form which include as the cation, the alkali metals, ammonium, and lower amine and alkanolamine.
  • linear paraflin sulfonates are also a well-known group of compounds and include water soluble salts (alkali metal, amine, alkanolamine, and ammonium) of:
  • linear alkyl sulfates which are contemplated in this invention comprise the range of C to C Specific examples include sodium n-decyl sulfate; sodium n-dodecyl sulfate; sodium n-hexadecyl sulfate; sodium n-heptadecyl sulfate; sodium n-octadecyl sulfate; and the ethoxylated (1 to moles ethylene oxide) derivatives; and, of course, the other water-soluble salt-forming cations mentioned above.
  • nonionic detergents such as alkaryl polyglycol detergents such as alkyl-phenol-ethylene oxide condensates (2-200 moles ethylene oxide), e.g., p-isooctyl phenolpolyethylene oxide (10 ethylene oxide units), long chain alcohol-ethylene oxide condensation products (2-200 moles ethylene oxide), e.g., dodecyl alcohol-polyethylene oxides having 4 to 16 ethylene oxides units per molecule, polyglycerol monolaurate, glycol dioleate, sorbitan monolaurate, sorbitan monostearate, sorbitan monopalmitate, sorbitan monooleate, sorbitan sesquioleate, the condensation products of ethylene oxide with sorbitan esters of long chain fatty acids (Tweens), alkylolamides, amine oxides, phosphine oxides, etc.
  • alkaryl polyglycol detergents such as alkyl-phenol-ethylene oxide condensates (2-
  • cationic, ampholytic, and zwitterionic compounds have also been found to be useful.
  • Representative of these compounds which may be employed in conjunction with the instant fabric softening compounds include quaternary ammonium compounds, e.g., distearyl dimethyl ammonium chloride, cetyl trimethyl ammonium bromide, sodium 3-dodecylamino propionate, fatty carbamides, etc.
  • composition of the instant invention may also include, in addition to the fabric softening compounds and conventional anionic, cationic, and nonionic detergent compositions, builders, brighteners, germicides, soil suspending agents, anti-redeposition agents, anti-oxidants, bleaches, coloring materials (dyes and pigments), perfumes, water-soluble alcohols, non-detergent alkali metal benzene sulfonates, etc.
  • the builder is, generally, a water-soluble, inorganic salt which may be a neutral salt, e.g., sodium sulfate or an alkaline builder salt such as phosphates, silicates, bicarbonates, carbonates, and borates.
  • a neutral salt e.g., sodium sulfate or an alkaline builder salt
  • phosphates, silicates, bicarbonates, carbonates, and borates e.g., sodium sulfate or an alkaline builder salt such as phosphates, silicates, bicarbonates, carbonates, and borates.
  • alkaline builder salt such as phosphates, silicates, bicarbonates, carbonates, and borates.
  • the preferred builders are those characterized as condensed phosphates such as polyphosphates and pyrophosphates.
  • alkaline salts are: tetrasodium, pyrophosphate, pentasodium, tripolyphosphate (either Phase I or Phase II), sodium hexametaphosphate, and the corresponding potassium salts of these compounds, sodium and potassium silicates, e.g., sodium metasilicate and alkaline silicates- (Na O; 2SiO and Na O; 3SiO sodium carbonate, potassium carbonate and sodium and potassium bicarbonate.
  • Other salts may also be used where the compounds are water-soluble. These include the general class of alkali metals, alkaline earth metals, amine, alkanolamine, and ammonium.
  • Other builders which are salts of organic acids may also be used, and in particular the water soluble (alkali metal, ammonium substituted ammonium and amine) salts of aminopolycarboxylic acids such as:
  • ethylene diamine tetra-acetic acid nitrilo triacetic acid diethylene triamine penta-acetic acid N-(Z-hydroxyethyl)-ethylene diamine triacetic acid Z-hydrQXyethyl-iminodiacetic acid 1,2-diaminocyclohexane diacetic acid, and the like.
  • the compounds useful in the instant fabric-softening composition may be combined in proportions ranging from about one part of the sulfolene derivative to about ten parts of the long chain alcohol, to about ten parts of the sulfolene derivative to about one part of the long chain aliphatic alcohol. Greater or lesser amounts of each of these ingredients may be employed depending upon the specific application for which the composition is prepared.
  • the fabric-softening composition may be combined with detergent and other additives in an amount ranging from 0.5% to 50% total fabric-softening composition.
  • a fabric-softening composition consisting essentially of (1) a five-membered heterocyclic compound selected from the group consisting of 3-sulfolene and substituted 3-sulfolenes; wherein the substituent groups are selected from the class consisting of alkyl having from 1 to 6 carbon atoms, alkoXy having from 1 to 4 carbon atoms, alkylalkoxy having from 1 to 18 alkyl carbon atoms and from 1 to 4 alkoxy carbon atoms, carboalkoxy, wherein the alkoxy group has from 1 to 4 car -hon atoms, N-alkyl and dialkyl carboxamidos, wherein the alkyl groups have from 1 to 2 carbon atoms, N-alkyl and dialkyl sulfonamidos, wherein the alkyl groups have from 1 to 2 carbon atoms, and halogen and (2) a branched or linear chain unsubstituted monohydric aliphatic alcohol having from to 22 carbon atoms, said five
  • composition of claim 1 wherein the five-membered heterocyclic compound is 3-sulfolene.
  • composition of claim 1 wherein the aliphatic alcohol is selected from the group consisting of decanol, undecanol, tridecanol, tetradecanol, pentadecanol, hexadecanol, heptadecanol, octadecanol, nonadecanol, eicosanol, heneicosanol, and docosanol.
  • composition of claim 3 wherein the five-membered heterocyclic compound is 3-sulfolene
  • composition of claim 4 wherein the aliphatic alcohol is l-hexadecanol.
  • a fabric-softening detergent composition comprising the fabric-softening composition of claim 1 and an organic detergent selected from the group consisting of anionic, nonionic and cationic synthetic detergents.
  • a composition as defined in claim 8 wherein the fabric-softening composition comprises 3-sulf0lene and l-hexadecanol in a weight ratio of from 1:10 and 10:1.
  • composition consisting essentially of (1) a five-mem'bered heterocyclic compound selected from the group consisting of 3-sulfolene and substituted 3-sulfolenes, wherein the substituent groups are selected from the class consisting of alkyl having from 1 to 6 carbon atoms, alkoxy having from 1 to 4 carbon atoms, alkylalkoxy having from 1 to 18 alkyl carbon atoms and from 1 to 4 alkoxy carbon atoms, carboalkoxy, wherein the alkoxy group has from 1 to 4 carbon atoms, N-alkyl and dialkyl carboxamidos wherein the alkyl groups have from 1 to 2 carbon atoms, N-alkyl and dialkyl sulfonamidos wherein the alkyl groups have from 1 to 2 carbon atoms and halogen and (2) a branched or linear chain unsubstituted monohydric aliphatic alcohol having from 10 to 22 carbon atoms, said
  • the aliphatic alcohol is selected from the class consisting of decanol, undecanol, tridecanol, tetradecanol, pentadecanol, hexadecanol, hep tadecanol, octadecanol, nonadecanol, eicosanol, heneicosanol, and docosanol.
  • HERBERT B. GUYNN Primary Examiner P. E. WILLIS, Assistant Examiner US. or. X.R. 117 1s9.5 252-86, 8.75, 152, 161.

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  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Textile Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
US682592A 1967-11-13 1967-11-13 Fabric softener composition Expired - Lifetime US3578591A (en)

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US68259267A 1967-11-13 1967-11-13

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US (1) US3578591A (es)
AT (1) AT291924B (es)
BE (1) BE723691A (es)
CA (1) CA930505A (es)
CH (1) CH489660A (es)
DE (1) DE1807446A1 (es)
DK (1) DK124346B (es)
ES (1) ES360141A1 (es)
FR (1) FR1590488A (es)
GB (1) GB1200000A (es)
IE (1) IE32924B1 (es)
NL (1) NL6815995A (es)
NO (1) NO128617B (es)
SE (1) SE343343B (es)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3793196A (en) * 1971-03-31 1974-02-19 Lion Fat Oil Co Ltd Softening agent
US3965014A (en) * 1972-12-07 1976-06-22 Colgate-Palmolive Company Anionic fabric conditioners
US4139477A (en) * 1978-03-16 1979-02-13 E. I. Du Pont De Nemours And Company Fabric conditioning compositions
US4213867A (en) * 1978-12-29 1980-07-22 Domtar Inc. Fabric conditioning compositions
US4242218A (en) * 1976-11-08 1980-12-30 Allied Chemical Corporation Phenol-free photoresist stripper
US20040151766A1 (en) * 2003-01-30 2004-08-05 Monahan Sean D. Protein and peptide delivery to mammalian cells in vitro
US8466100B2 (en) 2008-08-15 2013-06-18 The Procter & Gamble Company Benefit compositions comprising polyglycerol esters

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3793196A (en) * 1971-03-31 1974-02-19 Lion Fat Oil Co Ltd Softening agent
US3965014A (en) * 1972-12-07 1976-06-22 Colgate-Palmolive Company Anionic fabric conditioners
US4242218A (en) * 1976-11-08 1980-12-30 Allied Chemical Corporation Phenol-free photoresist stripper
US4139477A (en) * 1978-03-16 1979-02-13 E. I. Du Pont De Nemours And Company Fabric conditioning compositions
US4213867A (en) * 1978-12-29 1980-07-22 Domtar Inc. Fabric conditioning compositions
US20040151766A1 (en) * 2003-01-30 2004-08-05 Monahan Sean D. Protein and peptide delivery to mammalian cells in vitro
US8466100B2 (en) 2008-08-15 2013-06-18 The Procter & Gamble Company Benefit compositions comprising polyglycerol esters

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Publication number Publication date
GB1200000A (en) 1970-07-22
FR1590488A (es) 1970-04-13
NL6815995A (es) 1969-05-16
IE32924B1 (en) 1974-01-23
DK124346B (da) 1972-10-09
DE1807446A1 (de) 1969-07-03
CA930505A (en) 1973-07-24
ES360141A1 (es) 1970-10-16
IE32924L (en) 1969-05-13
NO128617B (es) 1973-12-17
CH1686768A4 (es) 1970-06-15
CH489660A (de) 1970-06-15
BE723691A (es) 1969-04-16
SE343343B (es) 1972-03-06
AT291924B (de) 1971-08-10

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