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Publication numberUS3712873 A
Publication typeGrant
Publication dateJan 23, 1973
Filing dateOct 27, 1970
Priority dateOct 27, 1970
Publication numberUS 3712873 A, US 3712873A, US-A-3712873, US3712873 A, US3712873A
InventorsZenk W
Original AssigneeProcter & Gamble
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Textile treating compositions which aid in the removal of soil from polyester and polyamide synthetic textile materials
US 3712873 A
Abstract  available in
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Claims  available in
Description  (OCR text may contain errors)

United States Patent O TEXTILE TREATING COMPOSITIONS WHICH AID IN THE REMOVAL OF SOIL FROM POLY- ESTER AND POLYAMIDE SYNTHETIC TEXTILE MATERIALS William Edward Zenk, Cincinnati, Ohio, assignor to The Procter & Gamble Company, Cincinnati, Ohio N Drawing. Continuation-impart of application Ser. No. 763,950, Sept. 30, 1968. This application Oct. 27, 1970, Ser. No. 84,482

Int. Cl. D06m 15/00, 3/30, 5/00 US. Cl. 260-292 E 8 Claims ABSTRACT OF THE DISCLOSURE Textile treating compositions comprising fatty alcohol polyethoxylates; quaternary ammonium compounds containing a single, long alkyl chain; a copolymer of a dibasic carboxylic acid and glycolic compounds; and either starch, carboxymethylcellulose, modified starch, polyethylene glycol, or copolymers of maleic anhydride and either methyl-vinyl-ether or ethylene; the process of treating synthetic textiles containing polyester or polyamide synthetic textile materials with the above compositions.

CROSS REFERENCE TO RELATED APPLICATION This application is a continuation-in-part of my application, Ser. No. 763,950 filed Sept. 30, 1968, now abandoned.

BACKGROUND OF THE INVENTION (1) Field of the invention This invention concerns textile treating compositions which can be applied by spraying or padding to textiles containing polyester or polyamide synthetic textile materials for the purpose of improving the soil-release characteristics of these materials.

(2) The prior art Fatty alcohol polyethoxylates are known detergent materials which are used, in dilute aqueous solutions, to clean textile materials. However, these fatty alcohol polyethoxylates have not, heretofore, been applied to clean polyamide textile materials, prior to soiling, for the purpose of aiding in the subsequent removal of soil.

Quaternary ammonium compounds containing a single, long alkyl chain have been disclosed for use in softening textile materials. See, e.g., the application of Charles B. McCarty, Ser. No. 829,093 filed May 29, 1969, now Pat. No. 3,649,569. Similarly, copolymers of dibasic carboxylic acids and glycolic compounds have been disclosed for use in improving the soil release characteristics of polyester synthetic textile materials. However, no one has suggested the combination of these materials would be particularly advantageous in providing soil-release properties for polyester and polyamide synthetic textile materials.

Starches, modified starches and ca-rboxymethylcellulose have all been suggested for use in treating textile mate rials either as sizes, or, in the case of carboxymethylcellulose, for the purpose of cleaning. Polyethylene glycols and copolymers of maleic anhydride with either methyl-vinylether or ethyelne have been disclosed for use in detergent compositions for washing textiles. However, the

3,712,873. Patented Jan. 23, 1973 above components have not been combined as set forth herein, or used as described herein.

SUMMARY OF THE INVENTION This invention relates primarily to a textile treating composition, which improves the soil-release characteristics of textiles containing polyester or polyamide synthetic textile materials, comprising:

(A) From about 1% to about 15% of the condensation product of a straight-chain fatty alcohol containing from about 16 to about 22 carbon atoms with from about 15 to about moles of ethylene oxide per mole of alcohol;

(B) From about 0% to about 4% of a compound having the formula wherein R is a straight-chain alkyl radical containing from about 16 to about 22 carbon atoms; each R is an alkyl group containing from one to about three carbon atoms; and X is selected from the group consisting of chloride, methyl sulfate, nitrate, bromide, and iodide anions;

(C) From about 0.1% to about 5% of a copolymer comprrsmg:

(1) A dibasic carboxylic acid of the following general formula wherein A is a bivalent organic radical selected from the group consisting of alkylene, arylene, aralkylene, alkarylene and cycloalkylene radicals, having from 3 to about 14 carbon atoms,

'(2) A glycolic compound which is a polyglycol selected from the group consisting of compounds of the following general formula wherein B is a bivalent organic radical selected from the group consisting of alkylene and cycloalkylene radicals, having from 2 to about 4 carbon atoms, and wherein n is an integer indicating the degree of polymerization and ranges from about 6 to about 500, and preferably (3) A glycolic compound which is a glycol selected from the group consisting of compounds having the following general formula wherein X is a bivalent organic radical selected from the group consisting of alkylene and cycloalkylene radicals having from 2 to about 4 carbon atoms, and wherein the molar ratio of dibasic acid to total glycolic compounds is 1:1 and the average molecular Weight of the copolymer is from about 1000 to about 100,000.

(D) From 0% to about 6% of a material selected from the group consisting of (1) alkali metal and ammonium carboxymethylcelluloses, (2) starch, (3) modified starches, (4) polyethyleneglycol having a molecular weight of from about 200 to about 8,000, (5) ethylene/ maleic-anhydride copolymers having specific viscosities of from about 0.1 to about 4.0 and, (6) methyl-vinylether/maleic-anhydride copolymers having specific viscosities of from about 0.1 to about 4, and

(E) The balance water.

This invention also relates to the process of applying to said textiles containing polyester or polyamide textile materials from about to about 50%, preferably from about to about 40%, by weight of the textiles, of the above textile treating compositions. For purposes of this invention, a textile is any material that is woven but does not include fibers before they have been woven into fabric.

DESCRIPTION OF THE INVENTION At this juncture, the textile treating compositions of this invention will be characterized in their entirety, in order to facilitate a better understanding of the individual components and their functions in these textile treating compositions.

The straight-chain fatty alcohol polyethoxylate The straight-chain fatty alcohol polyethoxylate is the primary ingredient of the composition which improves th soil-release characteristics of polyamide synthetic textile materials, e.g., nylon. Where the textile material is made entirely of polyamide textile material it is possible to achieve substantial improvement in the soil-release characteristics of textiles containing polyamides, e.g., nylon, by simply applying from about 0.5% to about 2%, y weight of the textiles, of the fatty alcohol polyethoxylate to the nylon textile material. A general purpose textile treating composition, however, would contain at least some of the other ingredients listed hereinbefore.

Suitable straight chain fatty alcohols can be derived from, e.g., tallow, hydrogenated soybean oil, hydrogenated rapeseed oil, etc. Synthetic fatty alcohols can also be used. The source of the fatty alcohol is not important. The number of moles of ethylene oxide used in forming the fatty alcohol polyethoxylate is from about 15 to about 60 moles of ethylene oxide per mole of fatty alcohol, preferably from about to about moles of ethylene oxide per mole of fatty alcohol. The preferred amount of the ethoxylate is from about 2% to about 10%.

The quaternary ammonium compound The quaternary ammonium compounds of this invention contain a single, straight long alkyl chain and three short alkyl chains. The long chain can be derived from tallow, hydrogenated soybean oil, hydrogenated rapeseed oil, etc. or can be derived from synthetic sources such as olefins prepared from ethylene. The source of the alkyl chains is immaterial. The short alkyl chains can be methyl, ethyl or propyl radicals. Any suitable water-solubilizing anions can be used as part of the quaternary ammonium salt. However, chloride and methyl sulfate anions are preferred.

The quaternary ammonium salt in combination with the polyester copolymer described hereinafter improves the soil-release characteristics of polyester synthetic materials. There should be from 0 to about 4% of the quaternary ammonium compound in the compounds of this invention preferably from about 0.5% to about 2% It has been discovered that other quaternary ammonium compounds such as the conventional ditallowalkyldimethylammonium chloride softening agent does not give the same superior performance obtained with the specific quaternary ammonium compounds of this invention. The same is true of certain well known quaternary ammonium compounds containing polyethoxylate chains in place of the short alkyl radicals.

The soil-release copolymer The copolymers which are effective, in combination with the quaternary ammonium compounds, in improving the soil-release characteristics of polyesters and/or polyamide synthetic textile materials are copolymers comprising (1) A dibasic carboxylic acid of the following general formula HOOCACOOH wherein A is a bivalent organic radical selected from he group consisting of alkylene, arylene, aralkylene, alkarylone and cycloalkylene radicals, having from 3 to about 14 carbon atoms,

(2) A glycolic compound which is a polyglycol selected from the group consisting of compounds of the following general formula wherein B is a bivalent organic radical selected from the group consisting of alkylene and cycloalkylene radicals, having from 2 to about 4 carbon atoms, and wherein the is an integer indicating the degree of polymerization and ranges from about 6 to about 500, and preferably (3) A glycolic compound which is a glycol selected from the group consisting of compounds having the following general formula HO-X-OH wherein X is a bivalent organic radical selected from the group consisting of alkylene and cycloalkylene radicals having from 2 to about 4 carbon atoms, and wherein the molar ratio of dibasic acid to total glycolic compounds is 1:1 and the average molecular weight of the copolymer is from about 1000 to about 100,000.

Where A is an alkylene radical, examples of suitable radicals are propylene, butylene, pentylene, octylene (methylene) ethylene, dodecylene and tetradecylene; where A is an arylene radical, examples of suitable radicals are phenylene and biphenylene; where A is an aralkylene radical, examples of suitable radicals are Z-phenylpropylene and Z-phenylbutylene; where A is an alkarylene radical, examples of suitable radicals are 2-propylphenylone and Z-ethylphenylene; and where A is a cycloalkylene radical, examples of suitable radicals are cyclobutylene, cyclopentylene, cyclohexylene, cyclooctylene and cyclotetradecylene. The preferred radical is phenylene, with the preferred dicarboxylic acid being terephthalic acid. Terephthalic acid is preferred as the dicarboxylic acid because it is an integral part of the polyester fiber structure. Butylene, biphenylene, and (methylene)ethylene are also preferred.

When B is an alkylene radical, examples of suitable radicals are ethylene, propylene and butylene. When B is a cycloalkylene radical, examples of suitable radicals are cyclopropylene and cyclobutylene. The preferred radical is ethylene and the preferred glycol is polyethylene glycol. Polyethylene glycol is preferred because it is the most hydrophilic of the polyglycols which can be used.

It should be noted that the polyglycol hereinbefore described has a degree of polymerization of from about 6 to about 500, e.g., from about 6 to about 500 alkenoxy or cycloalkenoxy groups make up the polyglycol chain. The polyglycol can be homopolymers of the individual glycol. The polyglycol can be copolymers of mixtures of the individual glycols with the individual glycols being randomly distributed in the polyglycol copolymer chain. In addition the polyglycol can be copolymers of mixtures of homopolymers of the individual glycols with the homopolymers being randomly distributed in the poly glycol copolymer chain. A homopolymer of ethylene glycol is preferred. The degree of polymerization of from about 6 to about 500 results in a polyglycol molecular weight of from about 300 to about 20,000. The preferred polyglycol degree of polymerization is from about 30 to about 40 with a preferred molecular weight of from about 1300 to about 1800. The preferred range of the degree of polymerization balances the structural similarity of the copolymers of this invention to the polyamide and/or polyester textile materials with the desired degree of hydrophilic character. Where the polyglycols used in preparing the anti-soiling copolymers are composed of higher molecular weight groups, i.e., where B has a higher molecular weight, the degree of polymerization is reduced to enable the anti-soiling copolymer to impart the desired soil-resistant properties to the polyamide and/or polyester fiber or fabric.

When X is an alkylene radical, examples of suitable radicals are ethylene, propylene and butylene. When X is a cycloalkylene radical, examples of suitable radicals are cyclopropylene and cyclobutylene. The preferred radical is ethylene and the preferred glycol is ethylene glycol.

The soil-release agent which is a copolymer in a 1:1 molar ratio of dibasic acid and total glycolic compounds, hereinbefore described, more specifically can be, for example, copolymers of terephthalic acid with polyethylene glycol, with polyethylene glycol and ethylene glycol, with polypropylene glycol, with polypropylene glycol and ethylene glycol, and with a copolymer of ethylene glycol and propylene glycol; copolymers of adipic acid with polyethylene glycol, with polyethylene glycol and ethylene glycol, with polypropylene glycol, with polypropylene glycol and ethyleneglycol, and with a copolymer of ethylene glycol and propylene glycol; and copolymers of itaconic acid with polyethylene glycol, with polyethylene glycol and ethylene glycol, with polypropylene glycol, with polypropylene glycol and ethyleneglycol, and with a copolymer of ethylene glycol and propylene glycol. All copolymers of the invention comprise the dibasic acid and glycolic compounds in a 1:1 molar ratio and said copolymers have an average molecular weight of from about 1000 to about 100,000. Preferably, when the glycolic component of the polymer comprises a polyglycol and a glycol, the molar ratio of polyglycol to glycol is from about :1 to about 2: 1.

The preferred soil-release agent is a copolymer of terephthalic acid, a polyethylene glycol having a degree of polymerization of about 35 and ethylene glycol, the three components being present in a molar ratio of acidzpolyglycolzglycol of 4.5 :3.5:1 (i.e. a 1:1 molar ratio of acid to total glycolic compounds, and 35:1 ratio of polyglycol to glycol) the average molecular weight of said copolymer being about 3000 to about 5000. A method for preparing copolymers of the type suitable for use in the invention herein is disclosed in British Pat. 1,092,435.

The polyester soil-release copolymers hereinbefore described are effective on polyester synthetic materials and to a somewhat lesser extent on polyester/cotton blends. They also provide a measure of improvement in the soilrelease characteristics of polyamide synthetic textile materials especially when used in combination with the fatty alcohol polyethoxylate described hereinbefore. There should be from 0.1% to about 5% of the polyester soilrelease copolymer in the compositions of this invention preferably from about 0.5% to about 2%.

Auxiliary soil-release additives There are five classes of hydrophilic polymeric materials which when added to the compositions of this invention provide improved soil-release characteristics for polyester and polyamide textile materials. These materials are (l) starches, (2) chemically modified starches, (3) carboxymethylcelluloses, (4) polyethylene glycols, and (5 copolymers of maleic anhydride with either ethylene or methyl-vinyl-ether. These specific polymeric additives provide a special improvement in soil-release characteristics where the treated textile materials are soiled or stained and then the textile materials are allowed to remain soiled, e.g., overnight. Some similar materials, e.g., polyvinylalcohol, do not provide as much improvement.

Suitable starches include corn starch and tapioca starch. Suitable chemically modified starches include alkali metal sulfate derivatives, amine and quaternary amine derivatives, and polyethoxylated derivatives wherein the degree of substitution is from about 0.05 to about 2, preferably from about 0.5 to about 1.5. An example of such a modified starch is NuFilm from National Starch and Chemical Company. Suitable carboxymethylcelluloses include sodium, potassium, ammonium and triethanolammonium carboxymethylcelluloses having a degree of substitution of from about 0.05 to about 2, preferably from about 0.5 to about 1.5. Suitable polyethylene glycols include those having molecular weights of 300, 400, 1000, 1300-1600, 4000 and 6000, preferably the polyethylene glycol has a molecular weight of from about 1000 to about 4,000. Suitable poly(methyl-vinyl-ether/maleic anhydride) materials include those having specific viscosities from about 0.1 to about 4, preferably from about 0.1 to about 1, as determined on a solution of one gram of the polymer in ml. of methyl ethyl ketone at 25 C. Suitable poly(ethylene/maleic anhydride) materials include those having a specific viscosity of from about 0.1 to about 4, preferably from about 0.1 to about 1 as determined on a 1% solution of the polymer in dimethyl formamide at 25 C. The specific viscosities disclosed hereinafter were measured as hereinbefore described,

The choice of a specific auxiliary soil-release additive will be dictated by the desired hand. These additives are also sizes and ironing aids.

The maleic anhydride copolymers can be used as the salts, either sodium, potassium, ammonium or triethanolammonium or can be esterified with the fatty alcohol/ ethylene oxide condensate.

The polyethylene oxides are very good soil-release additives, and it is not necessary to include the quaternary ammonium compounds when they are used. However, the quaternary ammonium compounds are preferred for optimum performance.

There should be from 0% to about 6% of these auxiliary materials in the composition, preferably from about 1% to about 4%.

The balance of the composition .is normally water, but may also contain from about 1% to about 20% of organic solvents such as methyl alcohol, ethyl alcohol, or isopropyl alcohol.

Other minor additives such as optical brighteners, pigments, dyes, perfumes, and silicones: and other ironing aids can also be present in minor amounts, e.g., up to about 1% of each ingredient. Of course, no soil-like material, such as oil, may be present in applicants compositions since such material naturally serves to defeat the soil release objectives of applicants invention.

The invention can be better understood by reference to the following examples. All percentages, parts and ratios herein are by weight unless otherwise specified.

'EXAMPLE '1 The following formulas were prepared and tested by spraying the formulas on Dacron and nylon cloths with an aerosol sprayer so as to coat the fabric evenly to make the cloths damp. The cloths were then air dried and soiled with used motor oil by adding three drops of motor oil to each treated section of the cloth. After a few minutes the treated and soiled cloths were placed in a miniature washer and washed for approximately ten minutes in water having a temperature of from about 100 F. to about F. and a hardness of seven grains. The water contained 6.7 grams per gallon of a conventional heavy-duty anionic detergent composition-Cheer. The cloths were then prerinsed for one minute in water having a temperature of 100 F. and a hardness of 7 grains. The cloths were then rinsed again with water having a temperature of 100 F. and a hardness of seven grains for two minutes. The cloths were then machine dried and evaluated. Compositions 1-6 were tested using cloths which were stained and then immediately washed and Compositions 7-15 were tested using cloths which were stained and allowed to set overnight.

The blank cloths which were not treated had heavy strains after washing.

The compositions in this example were used at a level of about 30% by weight of the textile material. The compositions of Examples II-X also provide excellent protection for the polyester and polyamide textile materials of this example when the compositions are applied at a level of about 30% by weight of the textile materials and the textile materials are then stained with motor oil.

Weight percent Composition 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 Tallow alcohol polyethoxylate moles). 4 2 4 4 4 4 4 4 4 4 Coconut alcohol polyethoxylatc moles)- Eicosyltrimethylammonium-chloride.

Ditallowalkyldimethylammonium chloride N-coconutalkyl-N,N-di[polyethoxy (15 moles)]-N-methyl ammonium chloride Octadecyltrimethylammonium chloride Copolymer of terephthalic acid polyethylene glycol (Degree of polymerizationabout 35) and ethylene glycol in a molar ratio of 4.53.521 and having an average molecular weight of 3,000 to 5,000

Sodium carbox methylcellulose Polyethylene glycol 1540 (MW. 1,600)

Poly(methyl-vinyl-ether/maleic anhydridc) specific viscosity of about 0.3; Gantrez AN 119 2 35% silicone oil-in-water emulsion (LE-463)- 1 1 Water Balance Alcohol 1 2 Composition- E MPLE III 1 Dacron-1 stam' Component: Weight, percent Nylon-slight stain. Dacron-significant reduction. Nylon-no stain. Dacron--slight reduction. Nylon-much reduced stain. Dacron-much reduction. Nylonlittle reduction Dacron-much reduction. Nylon-little reduction. Dacron-mo stain.

N ylon-no stain.

D aeron-much reduction. Nylon-very slight reduction. Dacron-very slight stain (1 spot). Nylon-very slight stain (2 spots). Dacronreduetion.

N ylon--reduetion. Dacron-reduction. Nylon-reduetion. Dacron-reduced. Nylon-very slight stain. Daeronmuch reduced.

N ylonreduced. Dacron-much reduction. Nylon-mueh reduction.

D acron-slight stain. Nylon-slight stain. Dacron-slight stain.

N ylon-very slight stain.

Compositions 1 and, especially, 6 show the overall advantage for the mixtures of ingredients of this invention over Compositions 2-5 which contain only single ingredients. A comparison of Composition 6 with Composition 7 shows the difr'erence when the stain is allowed to set overnight. A comparison of Composition 11 with Compositions 8, 12, 13, 14 and 15 shows the advantage of having the specific auxiliary soil-release additives of this invention present when a stain is allowed to set overnight. A comparison of Compositions 8, 9 and 10 show the advantage of the specific quaternary ammonium compounds of this invention over other conventional quaternary ammonium compounds.

EXAMPLE II about 3,500 1 Corn starch 1 Tapicoa starch 1 Isopropyl alcohol 3 Water Balance The condensation product of eicosyl alcohol and about 45 moles of ethylene oxide per mole of alcohol 2 Octadecyldimethylisopropylamrnoniurn iodide 1 A copolymer of terephthalic acid and a 1:1 copolymer of ethylene glycol and propylene glycol having a degree of polymerization of about and an average molecular weight of about 1500, with an acid to glycol copolymer molar ratio of 1:1 and an average molecular weight for the entire copolymer of about 5000 The sodium salt of sulfated corn starch having a degree of substitution of about 0.5 1

An amine substituted tapioca starch having a degree of substitution of about 1 1 A trimethylammoniumchloride substituted corn starch having a degree of substitution of about 1.5 1

Water Balance EXAMPLE V Component: Weight, percent The condensation product of tallow fatty alcohol and about 15 moles of ethylene oxide per mole of alcohol 3 Eicosyltripropylammonium nitrate 1 A copolymer of itaconic acid, polypropylene glycol having a degree of polymerization of about and ethylene glycol in a molar ratio of 4.5 :3.5 :1 and having an average molecular weight of about 4100 Component:

9 EXAMPLE V-Continued The condensation product of tallow alcohol and about 25 moles of ethylene oxide per mole of alcohol 4 Nonadecyltrimethylammonium chloride 2 A copolymer of itaconic acid, poly(1,2-cyclobutanediol) having a degree of polymerization of about 50 and propylene glycol in a molar ratio of 4.5 :3.5 :1 and having an average molecular weight of about 4,800 l A compolymer of 1,2-tetradecyl-dicarboxylic acid and poly(l,2-butanediol) having a degree of polymerization of about 60 with an acid to polymer molar ratio of 1:1 and an average copolymer molecular weight of about 4,000 1 A coloplmer of 1,2-cycloctalene dicarboxylic acid, polyethylene glycol having a degree of polymerization of about 100 and ethylene glycol in a molar ratio of 4.5 :3.5 :1 and having an aver- The condensation product of hexadecyl alcohol and about 17 moles of ethylene oxide per mole of alcohol 2 A copolymer of 6-propylphenylene-1,3-dicarboxylic acid, polypropylene glycol having a degree of polymerization of about 120 and propylene glycol in a molar ratio of 6:51 and having an average molecular weight of about 4,000 1 A copolymer of 2-phenylbutylene-1,2-dicarboxylic acid, polyethylene glycol having a degree of polymerization of about 80 and ethylene glycol in a molar ratio of 3 :221 and having an average molecular weight of about 3,000 1 Polyethyleneglycol having a molecular weight of about 2,000 2 Poly(methyl-vinyl-ether/maleic anhydride) having a specific viscosity of about 3 1 Water Balance EXAMPLE VIII Weight, percent The condensation product of eicosyl alcohol about 50 moles of ethylene oxide per mole of alcohol I0 Tallow trimethylamrnonium chloride l A copolymer of phenyl-1,4-dicarboxylic acid and olyethyleneglycol having a degree of polymerization of about 40 in a molar ratio of 1:1

and having an average molecular weight of Component:

Component:

Component 1 0 EXAMPLE VIHContinued Weight, percent A copolymer of itaconic acid, a (1:1) copolymer of ethylene glycol and propylene glycol having a degree of polymerization of about 20 and an average molecular Weight of about 1300, and ethylene glycol in an acid to copolymer to glycol molar ratio of 4:3:1 and having an average molecular weight for the entire copolymer of about 5,000 A copolymer of cyclobutylene 1,2-dicarb0xylic acid, polypropylene glycol having a degree of polymerization of about 70 and propylene glycol in a molar ratio of 4.5:3.5:l and having an average molecular weight of about 5,000 Poly(methyl-vinyl-ether/maleic anhydride) having a specific viscosity of about 3 Poly(methyl-vinyl-ether/maleic anhydride) having a specific viscosity of about 1.7 Poly(ethylene/maleic anhydride) having a specific viscosity of about 3.2 Polyethylene glycol having a molecular weight of about 1,000 3 Isopropyl alcohol 10 Water Balance EXAMPLE IX Weight, percent The condensation product of behenyl alcohol and about 50 moles of ethylene oxide per mole of alcohol 11 Tallow alkyl methyldiisopropylammonium methyl sulfate 1 The copolymer of cyclotetradecylene 1,2 dicarboxylic acid, polypropylene glycol having a degree of polymerization of about 10 and propylene glycol in a molar ratio of 5:3:2 and having an average molecular weight of about 4,000 The copolymer of cyclobutylene-l,Z-dicarboxylic acid and a 1:1 copolymer of ethylene glycol and propylene glycol having a degree of polymerization of about 40 and an average molecular weight of about 1800 and ethylene glycol in an acid to copolymer to glycol molar ratio of 4.5:3.5:l and having an average molecular weight for the entire copolymer of about 5,000 The copolymer of 2-phenylpropylene-1,3-dicarboxylic acid, polyethylene glycol having a degree of polymerization of about 60 and ethylene glycol in a molar ratio of 3:2:1 and having an average molecular weight of about 3,000 Polyethylene glycol having a molecular weight of about 300 2 Water Balance EXAMPLE X Weight, percent The condensation product of tallow alcohol and about 35 moles of ethylene oxide per mole of alcohol 4 Tallow alkyl trimethylammonium methyl sulfate 1 A copolymer of biphenylene-1,6-dicarboxylic acid,

a 1:1 copolymer of ethylene glycol and propylene glycol having a degree of polymerization of about 70 and an average molecular weight of about 1800 and propylene glycol in an acid to copolymer to glycol molar ratio of 4.513.521 and an average molecular weight for the entire copolymer of about 5,000 A copolymer of octylene-1,2-dicarboxylic acid,

polyethylene glycol having a degree of polymerization of about and ethylene glycol in a 4.5 :3.5 :1 molar ratio and having an average molecular weight of about 4,000 0.2

1 1 EMMY "LE XContinued a specific viscosity of about 1.2 0.1 Poly(maleic anhydride) having a specific viscosity of about 1.1 0.2 'Ethyl alcohol 7 Water Balance What is claimed is:

1 A textile treating composition which improves the resistance to soiling of textiles containing polyester or piglyamide synthetic textile materials consisting essentially o (A) from about 1% to about 15% of the condensation product of a straight-chain fatty alcohol containing from about 16 to about 22 carbon atoms with from about 15 to about 60 moles of ethylene oxide per mole of alcohol;

(B) from about 0.5 to about 4% of a compound having the formula wherein R is a straight-chain alkyl radical containing from about 18 to about 22 carbon atoms; each R is an alkyl group containing from one to about three carbon atoms; and X is selected from the group consisting of chloride, methyl sulfate, nitrate, bromide, and iodide anions;

(C) from about 0.1% to about 5% by weight of a soil-release agent, said soil-release agent being a copolymer consisting essentially of (1) an organic dicarboxylic acid selected from the group consisting of compounds of the following general formula wherein A is a selected from the group consisting of phenylene and biphenylene and (2) a glycolic compound which is a polyglycol selected from the group consisting of compounds of the following general formula wherein B is alkylene having from 2 to 4 carbon atoms, and wherein n is an integer indicating the degree of polymerization and ranges from about 6 to about 500; and wherein the ratio of dicarboxylic acid to glycolic compound is 1:1 and the average molecular weight of said copolymer is from about 1,000 to about 100,000;

(D) from to about 6% of a material selected from the group consisting of (1) alkali metal and ammonium carboxymethylcelluloses, (2) starch, (3) polyethyleneglycol having a molecular weight of from about 200 to about 8,000, (4) ethylene/maleic anhydride copolymers having specific viscosities of from about 0.1 to about 4 and (5) methylvinyl-ether/ maleic anhydride copolymers having specific viscosities of from about 0.1 to about 4.

(E) and the balance water.

2. The composition of claim 1 wherein the soil-release agent is a copolymer consisting of (1) an organic dicarboxylic acid selected from the group consisting of compounds of the following general formula wherein A is selected from the group consisting of phenylene and biphenylene (2) a glycolic compound which 12 is a polyglycol selected from the group consisting of compounds of the following general formula wherein B is alkylene having from 2 to 4 carbon atoms, and wherein n is an integer indicating the degree of polymerization and ranges from about 6 to about 500; and (3) a glycolic compound which is a glycol selected from the group consisting of compounds having the following general formula wherein X is alkylene having from 2 to 4 carbon atoms, and wherein the molar ratio of dicarboxylic acid to total glycolic compounds is 1:1 and the average molecular weight of said copolymer is from about 1,000 to 100,000.

3. The composition of claim 2 wherein A is phenylene, wherein B is ethylene, wherein X is ethylene, and wherein n is from about 30 to about 40 4. The composition of claim 3 wherein A is phenylene, wherein B is ethylene, wherein n is about 35, wherein X is ethylene, wherein the molar ratio of dicarboxylic acid: polyglycohglycol is 4523.5 :1 and wherein the average molecular weight of the copolymer is from about 3000 to 5000.

5. The composition of claim 2 containing from about 2% to about 10% of Component A from about 0.5% to about 2% of Component B; from about 0.5% to about 2% of Component C; and from about 1% to about 4% of Component D.

6. The composition of claim 3 wherein Component A is the condensation product of a straight chain fatty alcohol containing from about 16 to about 22 carbon atoms with from about 25 to about 35 moles of ethylene oxide per mole of fatty alcohol.

7. The composition of claim 2 containing from about 1% to about 20% of an organic solvent selected from the group consisting of methyl alcohol, ethyl alcohol, and isopropyl alcohol.

8. The composition of claim 2 wherein Component A is the condensation product of tallow alcohol and about 30 moles of ethylene oxide per mole of alcohol; wherein Component B is eicosyl trimethylammonium chloride; wherein Component C is a copolymer of terephthalic acid, a polyethylene glycol having a degree of polymerization of about 35, and ethylene glycol, in a molar ratio of terephthalic acid to polyethylene glycol to ethylene glycol of 4.5:3.5 :1 and having an average molecular weight of about 3000 to about 5000; and Component D is polyethylene glycol having a molecular weight of about 1500.

References Cited UNITED STATES PATENTS 2,803,565 8/1967 Sagar 2528.9 X 3,364,142 1/1968 Buck 2528.9 X 3,236,685 2/1966 Caldwell et a1 1l7-138.8 3,468,697 9/1969 Hunter 117139.5 3,583,912 6/1971 Clark 2528.8 3,509,049 4/1970 Zweidler 2528.8

FOREIGN PATENTS 1,088,984 10/ 1967 Great Britain. 1,119,368 7/ 1968 Great Britain.

OTHER REFERENCES Imperial Chemical Ind., Netherlands application 6614134, pub. Apr. 10, 1967. HERBERT B. GUYNN, Primary Examiner US. Cl. X.R.

117l38.8 N, 138.8 R, 139.5 C, Q; 2528.9; 260 -R, 16, 29.6 NR, 29.6 ME, 29.6 MN

Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3878151 *Oct 30, 1972Apr 15, 1975Basf AgThickeners for print pastes composed of cross-linked maleic anhydride-alkyl vinyl ether polymers
US3908048 *Apr 6, 1973Sep 23, 1975Kao CorpMethod of improving interfiber cohesion of filament yarns
US3928213 *Jun 29, 1973Dec 23, 1975Procter & GambleFabric softener and soil-release composition and method
US3959230 *Jun 25, 1974May 25, 1976The Procter & Gamble CompanySoil release agents
US3962152 *Jun 25, 1974Jun 8, 1976The Procter & Gamble CompanyDetergent compositions having improved soil release properties
US3981833 *Apr 1, 1975Sep 21, 1976Standard Oil Company (Indiana)Starch/polyester resin composition
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Classifications
U.S. Classification252/8.62, 524/549, 524/156, 524/236
International ClassificationD06M15/11, D06M15/09, D06M15/53, D06M15/01, D06M15/37, D06M15/21, D06M15/263
Cooperative ClassificationD06M15/263, D06M15/21, D06M15/09, D06M15/11, D06M15/53
European ClassificationD06M15/53, D06M15/21, D06M15/09, D06M15/11, D06M15/263