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Publication numberUS3578591 A
Publication typeGrant
Publication dateMay 11, 1971
Filing dateNov 13, 1967
Priority dateNov 13, 1967
Also published asCA930505A1, DE1807446A1
Publication numberUS 3578591 A, US 3578591A, US-A-3578591, US3578591 A, US3578591A
InventorsLazaridis Christina Nicholson, Wixon Harold Eugene
Original AssigneeColgate Palmolive Co
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Fabric softener composition
US 3578591 A
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Description  (OCR text may contain errors)

United States Patent US. Cl. 2528.7 13 Claims ABSTRACT OF THE DISCLOSURE A non-yellowing fabric-softening composition comprising a mixture of a sulfolene and an aliphatic alkanol which is designed for use in conjunction with anionic, cationic, and nonionic detergent compostions.

The present invention relates to a non-yellowing fabricsoftening composition which may be used in conjunction with other conventional laundering additives.

The art of treating textile materials with such agents as brighteners, softeners, antistatic agents, germicidal agents and the like is at this point a fairly well developed and commercially important industry. In almost every instance the finishing of the textile material is accomplished upon the said material from the finishing mill prior to its formation into a garment or wearing apparel. Some of the finishesapplied in the mill remain for a period of time-with the fabric, but others are removed after or during the first or subsequent washes of the textile mate rial. In the manner of finishing textile goods, fibers such as wool and cotton as well as synthetic fibers such as nylon, Dacron polyester, Orlon acrylic fiber and the like are equally in need of additional treatment to render the wearing properties of the garment acceptable to the trade. 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.

It is also well known that many of the treatments applied in mill finishing are not durably fixed to fabric. Because of this, desirable properties initially present on the fabric are lost after initial or subsequent washing of the fabric or garments made therefrom. It is obvious, therefore, that the various fabrics or garments need subsequent treatment by the consumer to realize utmost utility and comfort. I

The use of various and diverse chemical materials and particularly cationic quaternary ammonium compounds as softeners for textile products is very well known in the art. It is also Well known to employ such materials for their softening effect during the laundering operation and particularly in the rinse cycle of the laundering process. This technique has been necessitated by the fact that the softeners heretofore employed, being mainly cationic in nature, are not compatible with the major type of detergent used in the washing cycle. By far, the predominating type of detergent used in home laundering processes, is anionic in nature and more particularly is of the alkali metal higher-alkyl benzene sulfonate type. To employ a cationic substance, such as the aforementioned softeners, in conjunction with 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. As a consequence of these difliculties, it is absolutely necessary to add the presently available cationic softeners to the clothes in the absence of any anionic detergent and where this is done during washing it must he done during the rinsing cycle.

It is also well known that there is a tendency for laundered articles to yellow when treated with cationic agents. This yellowing of the textiles treated with cationics is believed to be caused by (1) highly colored impurities or by-products in some commercial cationic finishing agents or (2) the presence of high amounts of iron in the finishing agents that may cause staining typical of iron compounds or, (3) due to the presence of alkali when the materials treated with the cationics are ironed or pressed.

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.

It is therefore an object of the instant invention to provide a fabric-softening composition which may be used in conjunction with conventional detergent compositions.

A still further object of the instant invention is to provide a non-yellowing fabric-softening composition.

It is another object of the instant invention to provide a detergent composition containing therein a 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.

It is a further object of the instant invention to provide a fabric-softening composition which may be introduced simultaneously with conventional laundering detergents directly into the wash cycle in a process for the laundering of textiles.

It is yet a further object to provide a fabric-softening composition which may be employed in conjunction with detergents and other cleaning, brightening, and laundering additives in a single-step laundering operation.

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.

Still further objects and advantages of the instant invention will become apparent from the following more detailed description which appears hereinafter.

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. In particular, 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;

methylethoxy," ethylethoxy, propylethoxy, butylethoxy,'

The long-chain alcohols useful in the instant invention 1 include saturated aliphatic alcohols having from 16 to 22 carbon atoms. In particular 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.

While it is known in the prior art to use long-chain aliphatic alcohols as fabric softening agents, it has been found that the use of said alcohols alone does not provide a satisfactory fabric softening result. It has been unexpectedly found that when one combines one of the above 3- sulfolene compounds with a long-chain aliphatic alcohol, one obtains a fabric softener far superior to that which may be obtained by the use of either an aliphatic alcohol or the sulfolene alone as is demonstrated by the following examples:

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.

EXAMPLE 4 A washing machine test was conducted on a composition having the following present in the bath:

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.

EXAMPLE 5 The general procedure of Example 4 is followed,'except that the detergent formulations employed are as follows:

(a) Percent Fabric softener (as in Example 4) 10 Linear tridecylbenzene sulfonate 17 Sodium tripolyphosphate 70 Water Balance (b) Same as (a) except sulfonate is replaced by sodium lauryl sulfate.

(c) Same as (a) except sulfonate is replaced by nonyl phenol condensate with ten moles of ethylene oxide.

(d) A liquid formulation containing:

Percent Frabric softener as in (a) 10 Nonionic as in (c) 10 Potassium tetrapyrophosphate 25 Carboxy methylcellulose 10 Water Balance EXAMPLE 6 A rinse cycle fabric softening composition is prepared having the following components:

Percent Fabric softener as in Example 4 10 Sodium xylene sulfonate (active basis) 5 Water Balance Upon the addition of the above to the rinse cycle during the laundering operation, excellent softness comparable to the previous examples is obtained.

EXAMPLES 725 The following fabric softening compositions were also tested, both separately and in combination with the detergents and additives disclosed herein as being useful for their ability to impart softness to fabric:

All the above compositions were found to impart a satisfactory degree of softness.

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. Others are the 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.

Among the above-noted 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. It is clear, however, that 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.

In addition to the benzene sulfonates one 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.

Examples of suitable linear alkyl benzene sulfonates:

sodium n-decyl benzene sulfonate sodium n-dodecyl benzene sulfonate sodium n-tetradecyl benzene sulfonate sodium n-pentadecyl benzene sulfonate sodium n-hexadecyl benzene sulfonate and the corresponding lower alkyl substituted homologues of benzene as well as the salts of the cations previously referred to. Mixtures of these sulfonates may, of course, also be used with mixtures which may include compounds wherein the linear alkyl chain is smaller or larger than indicated herein provided that the average chain length in the mixture conforms to the specific requirements of C10 to C22- 6 The linear paraflin sulfonates are also a well-known group of compounds and include water soluble salts (alkali metal, amine, alkanolamine, and ammonium) of:

l-decane sulfonic acid l-dodecane sulfonic acid l-tridecane sulfonic acid l-tetradecane sulfonic acid l-pentadecane sulfonic acid l-hexadecane sulfonic acid as well as the other position isomers of the sulfonic acid group.

In addition to the parafiin sulfonates illustrated above, others with the general range of C to C alkyls may be used, with the most preferable range being from C to C20.

The 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.

Also useful in conjunction with the instant invention are 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.

In addition to the anionic and nonionic detergents which may be employed in conjunction with the instant invention, 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.

The 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. The preferred builders are those characterized as condensed phosphates such as polyphosphates and pyrophosphates. Specific examples of 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; namely, the sulfolene and the long-chain aliphatic alcohols, 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.

While various preferred embodiments of the present invention have been illustrated by means of specific examples, it is to be understood that the present invention is in no way to be deemed as limited thereto, but should be construed as broadly as all or any equivalents thereof.

What is claimed is:

, 1. 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-membered heterocyclic compound and said alcohol being present in a ratio of from 1:10 to 10:1.

2. The composition of claim 1 wherein the five-membered heterocyclic compound is 3-sulfolene.

3. The 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.

4. The composition of claim 3 wherein the five-membered heterocyclic compound is 3-sulfolene,

5. The composition of claim 4 wherein the aliphatic alcohol is l-hexadecanol.

I v6. The compound 0 claim 1 wherein the aliphatic alcohol is l-hexadecanol.

7. 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.

8. A composition as defined in claim 7 wherein the organic detergent is anionic.

9. 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.

10. The method of softening fabrics comprising treating said fabrics with a 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 five-membered heterocyclic compound and said alcohol being present in a ratio of from 1:10 to 10:1.

11. The method of claim 10 wherein the five-membered heterocyclic compound is 3-sulfolene.

12. The method of claim 10 wherein the aliphatic alcohol is selected from the class consisting of decanol, undecanol, tridecanol, tetradecanol, pentadecanol, hexadecanol, hep tadecanol, octadecanol, nonadecanol, eicosanol, heneicosanol, and docosanol.

13. The method of claim 12 wherein the aliphatic alcohol is l-hexadecanol.

References Cited UNITED STATES PATENTS 2,420,834 5/1947 Morris et al. 260-332.1 2,482,631 9/1949 Morris et al. -1 260332.1 2,734,830 2/1956 Hagge et a1. 117-1395 3,178,366 4/1965 'DuBrow et al. 2528.7S 3,192,231 6/1965 Welcher 260332.1

HERBERT B. GUYNN, Primary Examiner P. E. WILLIS, Assistant Examiner US. or. X.R. 117 1s9.5 252-86, 8.75, 152, 161.

Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3793196 *Apr 13, 1972Feb 19, 1974Lion Fat Oil Co LtdSoftening agent
US3965014 *Dec 7, 1972Jun 22, 1976Colgate-Palmolive CompanyAnionic fabric conditioners
US4139477 *Mar 16, 1978Feb 13, 1979E. I. Du Pont De Nemours And CompanySoftening, antistatic, improved water wicking, driers
US4213867 *Dec 29, 1978Jul 22, 1980Domtar Inc.Quaternary ammonium compounds and fatty alcohols or phosphoric esters of fatty alcohols
US4242218 *Nov 8, 1976Dec 30, 1980Allied Chemical CorporationAlkyl substituted aryl sulfonic acid
US8466100May 8, 2012Jun 18, 2013The Procter & Gamble CompanyBenefit compositions comprising polyglycerol esters
Classifications
U.S. Classification510/327, 510/505, 510/493, 510/515, 510/333, 510/526, 510/494
International ClassificationC11D3/00, D06M13/00, D06M13/248, D06M13/144, C11D3/34
Cooperative ClassificationD06M13/144, C11D3/349, C11D3/3481, D06M13/248, C11D3/001
European ClassificationC11D3/00B3, C11D3/34L, D06M13/144, D06M13/248