US3632420A - Textile material with improved soil release characteristics - Google Patents

Textile material with improved soil release characteristics Download PDF

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US3632420A
US3632420A US3632420DA US3632420A US 3632420 A US3632420 A US 3632420A US 3632420D A US3632420D A US 3632420DA US 3632420 A US3632420 A US 3632420A
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textile material
soil release
textile
fabric
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Hans H Kuhn
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Deering Milliken Research Corp
Milliken Research Corp
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    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS, OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • 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
    • D06M13/402Amides imides, sulfamic acids
    • D06M13/432Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; Carbodiimides; Guanidines, e.g. dicyandiamides
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2279Coating or impregnation improves soil repellency, soil release, or anti- soil redeposition qualities of fabric

Abstract

A textile material with improved soil release characteristics treated with a synthetic acid soil release polymer containing at least about 10 percent by weight acid calculated as acrylic acid and an amide compound having the formula
WHEREIN X is oxygen or sulfur, R1 is hydrogen, amino, alkyl, aryl or a substitutive derivative of such groups, and R2 and R3 are hydrogen, alkyl, amido or a substitutive derivative thereof; THE SOIL RELEASE POLYMER COMPRISING BETWEEN ABOUT 0.2 PERCENT AND 10 PERCENT BY WEIGHT OF THE TEXTILE MATERIAL AND THE AMIDE COMPOUND COMPRISING BETWEEN ABOUT 0.05 PERCENT AND 5 PERCENT BY WEIGHT OF THE TEXTILE MATERIAL.

Description

United States Patent [72 I inventor Hans H. Kuhn Spartanburg, S.C.

1211 Appl. No. 759,758

[22] Filed Sept. 13, 1968 l 45 I Patented Jan. 4, 1972 {73] Assignee Deering Milliken Research Corporation Spartanburg, S.C.

[54] TEXTILE MATERIAL WITH IMPROVED SOIL RELEASE CHARACTERISTICS 1 1 Claims, No Drawings [52] US. Cl ..117/138.8F, 117/76 T, 117/93.31, 117/138.8 A, l17/139.5 A, 117/143 A, 117/161 UC, 117/161 UN, 252/8.8 [51] 1nt.C1 ..D06m 15/16,

832k 27/06 [50] Field of Search 1 17/1395 CQ, 139.5 A, 161 UC, 161 UN, 138.8 U, 138.8 N, 138.8 F; 252/88; 8/1 15.6

[56] References Cited UNITED STATES PATENTS 2,262,770 11/1941 La Piana 8/115.6 2,415,112 2/1947 Seymouret al... l17/l37 2,795,513 6/1957 Rossin 117/138.8 N 2,904,541 9/1959 Barrett 117/138.8 N 2,922.726 1/1960 Moretti et a1. 1l7/138.8 N 2,945,013 7/1960 Ott 117/l38.8 N 2,980,733 4/1961 Sowa l17/l39.50 3,047,425 7/1962 I-Iirshfeld 117/1388 U 3,183,282 5/1965 Hurwitz ll7/l6l UlC 3,236,685 2/1966 Caldwell et al. 1 17/161 UlC 3,238,167 3/1966 Wolffet al. [17/161 UlC 3,377,249 4/1968 Marco 117/139.4

Primary ExaminerWilliam D. Martin Assistant Examiner-Ralph Husack Attorneys-Norman C. Armitage and H. William Petry ABSTRACT: A textile material with improved soil release characteristics treated with a synthetic acid soil release polymer containing at least about 10 percent by weight acid calculated as acrylic acid and an amide compound having the formula wherein X is oxygen or sulfur,

R is hydrogen, amino, alkyl, aryl or a substitutive derivative of such groups, and

R and R are hydrogen, alkyl, amido or a substitutive derivative thereof;

the soil release polymer comprising between about 0.2 percent and 10 percent by weight of the textile material and the amide compound comprising between about 0.05 percent and 5 percent by weight of the textile material.

TEXTILE MATERIAL WITH IMPROVED SOIL RELEASE CHARACTERISTICS The textile industry during the past decade has made important technological advances in the chemical finishing of textile materials. Numerous processes have been developed for imparting minimum care properties to garments and other articles prepared from specially treated textile materials. Among such advances are wash and wear fabrics and durable press fabrics.

Recently a great deal of interest has been directed toward imparting soil release characteristics to textile materials and particularly durable press textile materials (see US Pat. No. 3,377,249). With fabrics having soil release properties, it is possible to remove soil and stains to a substantially greater extent with conventional home laundering than is possible with fabrics without soil release. Soil release characteristics are particularly important with textile materials including hydrophobic fibers, e.g., polyesters, since generally such materials tend to retain stains to a greater degree and to absorb soil from wash water during laundering. Both of these problems are substantially eliminated by treatment with soil release chemicals.

in accordance with the present invention it has been found that an improvement in the soil release characteristics of textile material is provided by a process which comprises applying a soil release composition and an amide, thioamide or a derivative thereof, hereinafter referred to as amide compound.

Suitable amide compounds include those having the formula wherein X is oxygen or sulfur,

R is hydrogen, amino, alkyl, aryl or a substitutive derivative of such groups, and 1 R and R are hydrogen, alkyl, amido or a substitutive derivative thereof.

Not suitable as the amide compound additive in the process of the invention are methylol amides which are commonly used to provide durable press properties to textile material such as dimethylol ethylene urea.

Particularly useful in the process of the invention are urea and derivatives thereof including substituted ureas such as methyl-urea, dimethyl urea, etc., derivatives of urea, e.g., thiourea, biuret; and like compounds which liberate ammonia during the processing.

The amide compound may be applied together with the soil release chemicals or may be applied sequentially therewith. The proportion of the amide compound generaily comprises between about 0.25 and 5 percent of the pad bath and preferably about 0.5 and 3 percent thereof. Thus, the proportion of the amide compound based on the textile material advantageously is between about 0.05 and 5 percent by weight and preferably between about 0.1 and 3 percent.

The process of the present invention is useful in the treatment of a wide variety of textile materials made from natural or synthetic fibers or blends of such fibers. Examples of natural fibers include cotton, linen and flax. Suitable synthetic fibers include both regenerated cellulose fibers such as viscose rayon and synthetic polymeric fibers, for example, polyamides, acrylics and particularly polyesters and blends thereof. Durable press garments and articles generally are made from blends of polyester and cotton or rayon fibers. While the textile material undergoing treatment is preferably in the form of a fabric, the process of the invention also may be used to treat fibers, yarns, threads, and the like.

The soil release composition employed in the process of the present invention may include one or more of a large number of different soil release compounds and chemicals, for example, synthetic acid polymers, low-molecular-weight polyesters, fluorochemicals, and polymerizable monomers of such compounds for in situ formation of the soil release composition.

Synthetic acid polymers suitable as'the soil release composition of the present invention may be prepared from any of the polymerizable organic acids, i.e., those having reactive points of unsaturation, e.g., one of the acrylic acids. These-polymers may be homopolymers of the acids or interpolymers of an acid and other monomers copolymerizable therewith provided at least percent by weight-acidis present in the polymer. Examples of polymerizable acids that may be used are acrylic acid, maleic acid, fumaric acid, methacrylic acid, itaconic acid, crotonic acid, cinnamic acid, polymerizable sulfonic acids, polymerizable phosphoric acids, etc. Monomers that may be interpolymerized with the above acids include monomers capable of copolymerizing with the acids which will not adversely affect the polymer. Suitable monomers include esters of the above acids prepared by reacting an acid with an alkyl alcohol, e.g., acrylic esters such as ethyl acrylate, methyl acrylate, propyl acrylate, isopropyl acrylate, methyl methacrylate, ethyl methacrylate, butyl methacrylate, 2-ethylhexyl acrylate, butyl acrylate, etc.; alkyl fumarates, maleates, crotonates, cinnamates, etc.; vinyl halides; monomers having vinylidene groups; e.g., styrene, acrylonitrile, methylstyrene; substituted vinyl monomers, e.g., chlorostyrene, butadiene, etc. Various mixtures of the above polymers also may be employed in the process of the present invention-as well as salts of the acid polymers, e.g., sodium, potassium, lithium, ammonium salts, etc.

Examples of synthetic acid polymers that maybe used in the process of the present invention include the following combinations:

ethyl acrylate: acrylic acid ethyl acrylate: acrylic acid: acrylamide butyl acrylate: acrylic acid ethyl acrylate: methacrylic acid ethyl acrylate: itaconic acid methyl methacrylate: acrylic acid 2-ethyl hexyl acrylate: acrylic acid acrylamide: acrylic acid butyl acrylate: acrylic acid: acrylamide ethyl acrylate: acrylic acid: N-methylol acrylamide ethyl acrylate: acrylic acid: styrene ethyl acrylate: acrylic acid: hydroxypropyl methacrylate ethyl acrylate: acrylic acid: divinyl benzene ethyl acrylate: acrylic acid: allyl acrylamide ethyl acrylate: acrylic acid: glycidyl acrylate ethyl acrylate: sodium styrene sulfonate ethyl acrylate: crotonic acid styrene: acrylic acid ethyl acrylate: acrylic acid: hydroxyethyl methacrylate hydroxyethyl methacrylate: acrylic acid: acrylamide butyl acrylate: ethyl acrylate: acrylic acid As noted above, the acid polymer should contain at least about 10 percent by weight acid calculated as acrylic acid. Preferably, the acid polymer contains at least about 20 percent by weight acid and particularly between about 30 and percent acid. Copolymers of acrylic acid or methacrylic acid with an acrylate ester such as-ethyl acrylate are considered to be especially usefulv The soil release composition and amide compound preferably are applied in an aqueous medium. Advantageously, between about 0.5 and 20 percent and preferably between about 1 and 10 percent by weight of the soil release chemical is present in the aqueous solution or dispersion. In terms of the proportion of the soil release chemical on the textile material, it is desirable to have between about 0.2 and 10 percent by weight thereof based on the dry weight of the textile material and preferably between about 0.5 and 5 percent by weight.

The soil release composition may include other ingredients in addition to the soil release chemicals, for example, emulsifying agents, wetting agents, softeners and other compounds that enhance the physical characteristics of the textile materials. Durable press characteristics may be achieved by the application to a fabric of a textile resin or a vinyl monomer with dual functionality. Such durable press materials, together with any required catalysts, may be applied simultaneously with the soil release composition and amide compound or sequentially therewith.

The term textile resin according to the present invention includes both monomers and polymers which when applied to a textile material and reacted under proper conditions undergo polymerization and/or condensation and are transformed to the thermoset state. Textile resins that may be employed when practicing the present invention include epoxy, acetal, aminoplast resins, etc., with aminoplast resins being preferred. These nitrogen-containing resins when applied to a textile material in the presence of a catalyst at temperatures between about 100 and 300C. are transformed into the thermoset state. The cured textile resin on the textile material affords the textile material a durable press and/or wrinkle resistant characteristic.

Exemplary of the preferred aminoplast textile resins that may be employed according to the present invention are the urea formaldehydes, e.g., propylene urea formaldehyde, dimethylol urea formaldehyde, etc., melamine formaldehydes, e.g., tetramethylol melamines, pentamethylol melamines, etc., ethylene ureas, e.g., dimethylol ethylene urea, dihydroxy dimethylol ethylene urea, hydroxy ethylene urea formaldehyde, etc.; carbamates, e. g., alkyl carbamate formaldehydeacetone condensation products; diureas, e.g., trimethylol acetylene diurea, tetramethylol-acetylene diurea, etc.; triazones, e.g., dimethylol-N-ethyl triazone, N-N' ethylene-bis dimethylol triazone, halotriazones, etc.; haloacetamides, e.g., N-methylol-N-methylchioroacetamide, etc.; urons, e.g., dimethylol uron, dihydroxy dimethylol uron, etc., and the like. Mixtures of aminoplast textile resins are also within the scope of the present invention,

Vinyl monomers having dual functionality within the scope of the present invention include acrylamides, e.g., N-methylol acrylamide, N-methylol methacrylamide, N-methylol-N- methacrylamide, N-methylmethylol acrylamide, N-methylol methylene-bis-(acrylamide), methylene-bis-(N-methylol acrylamide), etc.; haloethylene acrylamide; and similar compounds which conform to the structural formulas set forth in U.S. Pat. No. 3,377,249.

The amount of textile resin or vinyl monomer with dual functionality applied to the fabric is primarily determined by the ultimate use of garments or articles prepared from the fabric. Very small amounts will afford some improvements and large amounts even greater improvements, but the larger amounts may adversely affect the hand of the fabric. Hence, the amount employed is preferably that which will afford good crease retention and flat dry properties while not adversely affecting the hand. For the purposes of the present invention, the amount of textile resin or vinyl monomer in the pad bath may be between about 2 and 30 percent. The proportion present on the fabric should be between about 2 and percent based on the dry weight of the fabric and preferably between about 4 and 9 percent.

Catalysts employed within the scope of the present invention depend upon the specific textile resin or vinyl monomer that is applied to the textile material. For instance, if the textile resin has a functional group that is reactive under acidic conditions, an acid catalyst is used. Likewise, when a functional group is present that is reactive under conditions, a base catalyst is used. Furthermore, both acid and base catalysts may be used when both type functional groups are present in the'textile resin. ln this instance, the catalyst may be added separately or simultaneously. When added simultaneously, one must be a latent catalyst, i.e., one that will not initiate its reaction during the opposite type reaction, but will be activated subsequently under proper catalytic conditions.

The catalysts useful in activating the acid or base reactive groups are those conventionally used to activate the reaction of textile resins containing the same group. Preferably, latent acid or base acting catalysts are utilized, that is, compounds which are acidic or basic in character under the curing conditions. The most common acid acting catalysts are the metal salts, for example, magnesium chloride, zinc nitrate and zinc fluoborate and the amino salts, for example, monoethanolamine hydrochloride and 2-amino-2-methylpropane! nitrate.

The base acting catalyst preferably is a compound which does not initiate substantial reaction of the base reactive group under normal acid conditions, but does initate substantial reaction under prescribed conditions such as elevated temperature or some other activating means, as through use of another chemical compound. For example, an alkali metal sulfite can be padded onto the fabric and be decomposed into strongly basic alkali metal hydroxide by including small amounts of formaldehyde in the steam used for curing.

The latent base acting catalyst utilized herein preferably comprises an alkali metal salt such as an alkali metal carbonate, e.g., sodium carbonate, which is neutral to mildly alkaline pH, for example, about 8.5, on the fabric but decomposes at temperatures in excess of about C. to form the stronger base sodium oxide which will initiate substantial reaction at the elevated temperatures utilized during curing. Sodium carbonate may be utilized if desired since the pH on the fabric produced by this compound under normal conditions is generally insufficient to initiate the desired degree of reaction at temperatures normally employed. lf fabrics containing a base reactive group are maintained at pH levels above about l0, however, degradation occurs so that essentially neutral or mildly alkaline catalysts are preferred when base reactive compounds are utilized.

Suitable base acting catalysts include potassium bicarbonate, potassium carbonate, sodium silicate, alkali metal phosphates such as sodium or potassium phosphates, barium carbonate, quaternary ammonium hydroxides and carbonates, for example, lauryl trimethyl ammonium hydroxides and carbonates and the like.

The amount of catalyst to be utilized is that conventionally used in activating the reaction, for example, up to about 15 percent by weight of an acid acting catalyst in the application bath with the preferred range being from about I to about 7 percent. A preferred range for the base acting catalyst is again the conventional amount and is generally between about 0.2 to about 16 percent, preferably about 2 to l6 percent. The amount of catalyst to be utilized will further depend in part on the temperature at which the reaction is conducted and the amount of catalyst consumed in the reaction. For example, when base catalysts are utilized and if a highly acidic group is released during the reaction, the amount of base applied to the textile material should be at least sufficient to provide an excess of base in addition to that which is consumed by the highly acidic group.

Separate or simultaneous application of the textile resin and the soil release composition may be employed. For instance, when treating a textile fabric which is to be converted into work clothes, it may be desirable to have as durable a finish as possible so that the soil release properties will be as long lasting as possible. In this situation, either a simultaneous addition or a separate addition where the soil release polymer is added first may be desirable. On the other hand, where the ultimate article of manufacture is not one that will be washed or cleaned on a weekly basis, for instance, the desirable property might possibly be to have a very superior initial soil release property. An example would be upholstery for automobiles, seat covers, wall coverings, etc. For these items it may be more desirable to apply first the textile resin and separately after curing of the textile resin apply the soil release composition or just apply the soil release composition, etc., as described herein, if a textile resin is not desired. it must be emphasized, however, that under such conditions the soil release properties may be less durable than those attained by the aforesaid simultaneous means of application.

Advantages afforded by the process of the present invention are available for textile materials treated in almost any form, e.g., fibers, yarns, threads, fabrics or the ultimate product, e.g., a garment, etc. Garments made from the fabrics treated according to the process of the present invention require no additional steps than those normally required for the preparation of the conventional durable press garments. In other words, the garment may be folded and pressed on conventional equipment,for example, a I-Iofiman press. The pressing cycle utilized is standard in the industry and generally involves pressing of the garment for a short period of time, followed by a curing operation in an oven. Alternatively, the garment may be set in a desired configuration under hot, dry conditions, such as by hot pressing without steaming, for example, at temperatures up to about 300 C. for as long as necessary to cure the resin.

In general, the textile resin may be selected from several general types. According to the type of resin selected, one of the following processes may be generally followed to achieve the novel garments produced by the present invention. In each type of procedure, the methods of application and order of application of textile resin, soil release composition, catalysts, etc., may be varied as described supra.

TYPE I 1. Apply textile resin having one type of functional group, textile resin catalyst, soil release composition and amide compound to fabric.

2. Dry fabric at a temperature insufficient to initiate catalysis of the textile resin.

3. Make garment from fabric.

Press garment to produce creases where desired.

. Subject garment to temperature sufficient to catalyze and cure the textile resin.

TYPE 11 Apply textile resiri and textile resin catalyst to fabric. Dry fabric at a temperature insufficient to initiate catalysis of the textile resin. 3. Apply soil release composition and amide compound to fabric. Prepare garment from the fabric. Press creases where desired in garment.

Subject garment to conditions sufficient to cure textile resin.

TYPE 111 Apply vinyl monomer with dual functionality, a textile resin catalyst, soil release composition and an amide compound to the fabric.

2. Dry the fabric at temperatures such that the textile resin catalyst remains dormant.

. Subject the fabric to irradiation.

. Make a garment from the fabric.

Produce desired creases in the garment.

Subject the garment to textile resin curing conditions.

Type 111 may be modified to provide a separate application of the soil release composition and the amide compound.

In each of the above types of procedures, the ultimate curing may be accomplished prior to the manufacture of the garment whereby a good wash and wear fabric having soil release properties is produced.

While the above procedures relate to the process of the present invention being applied to a textile material to afford the textile material soil release and durable press or wash and wear characteristics, other materials also may be applied to the fabric as desired according to the description herein.

The drying temperatures that are insufficient to initiate the catalysis are dependent upon the particular catalyst being employed. In general, however, the drying step is conducted at a rate of approximately to 70 yards per minute at temperacient to initiate catalysis that would at least partially cure the textile resin.

Irradiation techniques may be employed according to the process of the present invention when a vinyl monomer having dual functionality is applied to the textile material. An insulated core transformer, operated at a potential varying between 100,000 and 500,000 electron volts may'be successfully used to irradiate the textile material. Such a'transformer is commercially available from High Voltage Engineering Corporation, Burlington, Mass. The amount of ionizing irradiation necessary according to the present invention is at least about 32 electron volts for each ion pair formed. Bothhigh energy particle and ionizing irradiation are .useful according to the present invention. The preferred dosage ofirradiation according to the present invention is in the range of 1,000 rads to I00 megarads, a rad being the amount of-high energy irradiation of the type which results in energy absorption of ergs per gram of absorbing material. More preferably, the irradiation dosage ranges from about 0.5 to 5 megarads.

Curing of the textile resin is accomplished with mixed synthetic-cellulosic textiles by subjecting the textile material having the textile resin thereon to conditions such that the catalyst initiates a cross-linking reaction and converts the resin to the thermoset state. When a 100 percent synthetic fabric is treated, the resin adheres to the material and is converted to a thermoset state. Temperature is the prime mover and generally a temperature in the range of about 100 to 300 C. is sufficient. The curing medium that supports the necessary temperature may be any substance which is inert to both the fabric and the ingredients applied thereto, e.g., hot air, steam, etc. In the instance where the textile resin possesses two different types of functional groups, there are actually two curing steps, the first being conducted at a temperature lower than the second and insufficient to initiate the second type of catalysis, e.g., a first partial curing step to initiate alkaline catalysis and a subsequent curing step to initiate acid catalysis and also convert the resin to the thermoset state.

The duration of the various processing steps will depend upon the particular ingredients employed. In each situation, however, the treatment time is that necessary to cause reaction of and/or curing of the textile resin, and preferably, between 0.1 and 30 minutes.

The following examples illustrate preferred embodiments of the present invention but are not intended to restrict the scope of the invention. In the examples, parts and percentages are by weight. The fabrics prepared in accordance with the procedures set forth in the examples are tested for soil release according to the following procedure. The soil release values are determined by comparison with a set of standards having numerical ratings from 1.0 to 5.0, with 1.0 representing no stain removal and 5.0 being complete removal of the stain. The fabrics are stained with mineral oil. After staining, the fabric is washed one time in a Kenmore automatic washer using normal cycle with one cup of Tide detergent (sold by Proctor and Gamble) and a wash water temperature of about F. The fabric is dried for approximately 40 minutes ata temperature of about F. The stains in the dried fabric are compared with the set of standards. The values listedin the tables under the headings 5, 10 and 20 washes represent staining after 5, 10 or 20 normal washings and then a single wash to remove the stain.

EXAMPLEI A poplin fabric made from polyester and cotton fibers (65/37 percent blend) is treated with an aqueous mixture containing about 18 percent N-methylol acrylamide (50 percent aqueous solution), l.5 percent of a polyethylene (Lubritron KN) and 0.1 percent ethoxylated nonyl phenol. The fabric is dried at a temperature of about 185 F. for about 2 minutes and then irradiated with a Z-megarad dose by passing the fabric through irradiation equipment having an insulated core transformer manufactured by the High Voltage Equipment Corporation of Burlington, Mass. The fabric is washed with water and dried in an oven to normal moisture regain. Thereafter the fabric is treated with an aqueous mixture containing about 35 percent emulsion copolymer of 75 percent methacrylic acid and 25 percent ethylacrylate percent solids), 4.3 percent zinc nitrate catalyst (50% Zn(NO 6H O), 0.1 percent ethoxylated nonyl phenol, 1.5 percent softeners and 2 percent urea. After the above bath is padded onto the fabric to provide about 50 percent wet pickup, the fabric is dried to about normal moisture regain. The fabric is cured in an oven at about 325 F. for about 15 minutes.

A control sample of the same fabric is processed according to the above procedure except the urea is omitted from the second bath. The results of the soil release tests for each of the fabrics is as follows:

While a single after wash of the control sample will raise the soil release rating close to 4.0, the use of urea eliminates the requirement for such an extra wash to achieve high initial soil release.

EXAMPLE II A fabric similar to that employed in example I is treated with an aqueous mixture containing 24 percent Reactant 100 (dihydroxy dimethylol ethylene urea-50 percent solution), 4 percent M-4 catalyst (mixture of 50% MgCl -6H O and 50% Zn(NO 6H O) and 0.1 percent wetting agent.

The above fabric having about 50 percent wet pickup is dried to about normal moisture regain, cured at 325 F. for 90 seconds and then treated with an aqueous mixture containing about 15 percent of the emulsion copolymer of example I, 1.3 percent softeners and 0.5 percent urea. The fabric then is dried to about normal moisture regain and cured in an oven at a temperature of about 325 F. for about 90 seconds.

A control sample of the fabric is processed according to the above procedure except the urea is omitted from the second bath. The results of the soil release tests for the above fabrics are as follows:

A fabric similar to that employed in example I is treated with an aqueous mixture containing 18 percent N-methylol acrylamide (60 percent aqueous solution), 4 percent zinc nitrate catalyst. I percent softener, 30 percent Acrysol ASE-60 (emulsion copolymer of about 40-60 percent methacrylic acid and 40-60 percent ethylacrylate, sold by Rohm and Haas) and 2 percent urea. Thereafter the fabric is dried and irradiated according to the procedure of example I. The irradiated fabric then is washed with water and dried to about normal moisture regain and cured at about 325 F. for 15 minutes.

A control sample of the fabric is processed according to the above procedure except the urea is omitted from the bath.

The results of the soil release tests are as follows:

Soil Release Washes Urcu Control As Received 3.2 2.2

EXAM PLE IV Soil Release Washes 8% Urea Control As Received 3.2 1.6

EXAMPLE V The procedure of this example is the same as that of example I except 40 percent of an emulsion copolymer of percent ethyl acrylate and 30 percent acrylic acid is added to the first bath. The results achieved are about the same as those of example I.

EXAMPLE VI The procedure of this example is the same as that of example 1 except the urea is replaced with thiourea. The results are similar to those achieved in example I.

EXAMPLE VII The procedure of this example is the same as that of example II except the urea is replaced with methyl urea. The results of the soil release tests are similar to those of example II.

The above description and examples show that the present invention provides a novel process for improving the soil release characteristics of textile material and particularly the soil release characteristics of textile material prior to initial laundering.

It will be apparent from the above that various modifications in the formulations and procedures described in detail may be made within the scope of the invention. Therefore, it is intended that the invention be limited only by the following claims.

That which is claimed is:

1. A textile material with improved soil release characteristics treated with a synthetic acid soil release polymer containing at least about 10 percent by weight acid calculated as acrylic acid and a urea compound of urea, methyl urea, dimethyl urea, thiourea or biuret; said soil release polymer comprising between about 0.2 and 10 percent by weight of the textile material and said urea compound comprising between about 0.05 and percent by weight of the textile material. 7

2. A textile material according to claim 1 wherein said urea compound is urea.

3. A textile material according to claim I wherein the synthetic acid polymer is a copolymer comprising an acrylic ester and an acrylic acid.

4. A textile material according to claim 3 wherein the synthetic acid polymer is a copolymer comprising between about 10 and 80 percent by weight of an acrylic ester and between about and 90 percent by weight of an acrylic acid.

5. A textile material according to claim 1 wherein the textile material includes polyester fibers.

Claims (10)

  1. 2. A textile material according to claim 1 wherein said urea compound is urea.
  2. 3. A textile material according to claim 1 wherein the synthetic acid polymer is a copolymer comprising an acrylic ester and an acrylic acid.
  3. 4. A textile material according to claim 3 wherein the synthetic acid polymer is a copolymer comprising between about 10 percent and 80 percent by weight of an acrylic ester and between about 20 percent and 90 percent by weight of an acrylic acid.
  4. 5. A textile material according to claim 1 wherein the textile material includes polyester fibers.
  5. 6. A textile material according to claim 1 wherein the textile material is a polyester and cellulosic textile material.
  6. 7. A textile material according to claim 1 treated with a textile resin.
  7. 8. A textile material according to claim 7 wherein the textile resin is an aminoplast textile resin.
  8. 9. A textile material according to claim 7 wherein the textile resin comprises a methylol ethylene urea.
  9. 10. A textile material according to claim 1 treated with an acrylamide.
  10. 11. A textile material according to claim 10 wherein the acrylamide is N-methylol acrylamide.
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Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3879300A (en) * 1972-10-25 1975-04-22 Colgate Palmolive Co Diamine containing softener compositions
DE2846984A1 (en) * 1977-11-02 1979-05-10 Rhone Poulenc Ind New for cleaning purposes usable anti-dirt and anti-redepositing compositions
US4214997A (en) * 1977-10-26 1980-07-29 Lever Brothers Company Soil-release compositions
US4758378A (en) * 1986-04-23 1988-07-19 The Procter & Gamble Company Softening detergent compositions containing amide softening agent
US5182044A (en) * 1990-06-01 1993-01-26 Lion Corporation Zeolite containing liquid detergent composition
US5968207A (en) * 1998-02-20 1999-10-19 Milliken & Company Esterified triclosan derivatives as improved textile antimicrobial agents
US6025284A (en) * 1997-12-01 2000-02-15 Marco; Francis W. Sun protective fabric
US6033608A (en) * 1998-03-11 2000-03-07 Milliken & Company Method for making foam rubber tree bark-configured articles having manmade textiles backings
US6180178B1 (en) 1998-10-22 2001-01-30 Milliken & Company Method of producing support garments by applying polyurethane coatings to specific areas of fabric
US6194330B1 (en) 1998-07-31 2001-02-27 Milliken & Company Polymer latex for ultraviolet absorbtion on fabric
US6263707B1 (en) 1999-09-20 2001-07-24 Milliken & Company Opaque heat-moldable circular knit support fabrics having very high spandex content
US6584668B2 (en) 2000-06-02 2003-07-01 Milliken & Company Method of manufacturing yarns and fabrics having a wash-durable non-electrically conductive topically applied metal-based finish
US20030200613A1 (en) * 2000-06-02 2003-10-30 Green David E. Topical incorporation of solid antimicrobial compounds on yarn surfaces through high pressure methods
US6770581B1 (en) 2000-03-17 2004-08-03 Milliken & Company Absorbent fabrics, products, and methods
US6774067B2 (en) 2000-03-17 2004-08-10 Milliken & Company Mat and method of manufacturing a mat
US20040224587A1 (en) * 2002-12-17 2004-11-11 Hayes Heather J. Fluorochemical-containing textile finishes that exhibit wash-durable soil release and moisture wicking properties
US20070050912A1 (en) * 2005-09-02 2007-03-08 Materniak Joyce M Reduction of turmeric and iodine staining
US20090246258A1 (en) * 2008-03-28 2009-10-01 Piyush Shukla Antimicrobial and odor adsorbing textile

Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2262770A (en) * 1941-04-01 1941-11-18 Stein Hall & Co Inc Sizing and finishing composition
US2415112A (en) * 1943-01-27 1947-02-04 Celanese Corp Flame and fireproofing of textile materials
US2795513A (en) * 1954-01-27 1957-06-11 Monsanto Chemicals Process for finishing textile material and product
US2904541A (en) * 1953-12-23 1959-09-15 Monsanto Chemicals Continuous polymerization processes and resulting products
US2922726A (en) * 1955-03-18 1960-01-26 American Cyanamid Co Flame-proofing nylon with thiourea containing resin
US2945013A (en) * 1956-03-22 1960-07-12 Monsanto Chemicals Water-soluble interpolymers of acrylic acids and 2-ethylhexyl esters of acrylic acids and method of making same
US2980733A (en) * 1954-07-12 1961-04-18 Frank J Sowa Coordination complexes of urea and boron trifluoride and methods of producing the same
US3047425A (en) * 1959-07-16 1962-07-31 Monsanto Chemicals Method for producing flame and soil resistant acrylic polymer fibers containing carpet fabric
US3183282A (en) * 1956-07-27 1965-05-11 Rohm & Haas Non-aqueous solutions of acrylic ester/acid copolymer and thermosetting alkylated aminoplast resin-forming condensate
US3236685A (en) * 1962-06-20 1966-02-22 Eastman Kodak Co Process for treating textile fibers and other shaped products with coatings
US3238167A (en) * 1962-10-08 1966-03-01 Staley Mfg Co A E Polymeric coating composition comprising an aminoplast and an emulsion copolymer of an ethylenically unsaturated ester of a mono carboxylic acid and an alkyl half-ester of itaconic acid
US3377249A (en) * 1966-08-04 1968-04-09 Deering Milliken Res Corp Soil release of polyester containing textiles through treatment with aminoplast resins in conjunction with acrylic emulsion polymers containing at least 20% acid calculated as acrylic acid

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2262770A (en) * 1941-04-01 1941-11-18 Stein Hall & Co Inc Sizing and finishing composition
US2415112A (en) * 1943-01-27 1947-02-04 Celanese Corp Flame and fireproofing of textile materials
US2904541A (en) * 1953-12-23 1959-09-15 Monsanto Chemicals Continuous polymerization processes and resulting products
US2795513A (en) * 1954-01-27 1957-06-11 Monsanto Chemicals Process for finishing textile material and product
US2980733A (en) * 1954-07-12 1961-04-18 Frank J Sowa Coordination complexes of urea and boron trifluoride and methods of producing the same
US2922726A (en) * 1955-03-18 1960-01-26 American Cyanamid Co Flame-proofing nylon with thiourea containing resin
US2945013A (en) * 1956-03-22 1960-07-12 Monsanto Chemicals Water-soluble interpolymers of acrylic acids and 2-ethylhexyl esters of acrylic acids and method of making same
US3183282A (en) * 1956-07-27 1965-05-11 Rohm & Haas Non-aqueous solutions of acrylic ester/acid copolymer and thermosetting alkylated aminoplast resin-forming condensate
US3047425A (en) * 1959-07-16 1962-07-31 Monsanto Chemicals Method for producing flame and soil resistant acrylic polymer fibers containing carpet fabric
US3236685A (en) * 1962-06-20 1966-02-22 Eastman Kodak Co Process for treating textile fibers and other shaped products with coatings
US3238167A (en) * 1962-10-08 1966-03-01 Staley Mfg Co A E Polymeric coating composition comprising an aminoplast and an emulsion copolymer of an ethylenically unsaturated ester of a mono carboxylic acid and an alkyl half-ester of itaconic acid
US3377249A (en) * 1966-08-04 1968-04-09 Deering Milliken Res Corp Soil release of polyester containing textiles through treatment with aminoplast resins in conjunction with acrylic emulsion polymers containing at least 20% acid calculated as acrylic acid

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3879300A (en) * 1972-10-25 1975-04-22 Colgate Palmolive Co Diamine containing softener compositions
US4214997A (en) * 1977-10-26 1980-07-29 Lever Brothers Company Soil-release compositions
DE2846984A1 (en) * 1977-11-02 1979-05-10 Rhone Poulenc Ind New for cleaning purposes usable anti-dirt and anti-redepositing compositions
US4758378A (en) * 1986-04-23 1988-07-19 The Procter & Gamble Company Softening detergent compositions containing amide softening agent
US5182044A (en) * 1990-06-01 1993-01-26 Lion Corporation Zeolite containing liquid detergent composition
US6025284A (en) * 1997-12-01 2000-02-15 Marco; Francis W. Sun protective fabric
US5968207A (en) * 1998-02-20 1999-10-19 Milliken & Company Esterified triclosan derivatives as improved textile antimicrobial agents
US6197072B1 (en) 1998-02-20 2001-03-06 Milliken & Company Esterified triclosan derivatives as improved textile antimicrobial agents
US6033608A (en) * 1998-03-11 2000-03-07 Milliken & Company Method for making foam rubber tree bark-configured articles having manmade textiles backings
US20030144410A1 (en) * 1998-07-31 2003-07-31 Vogt Kirkland W. Polymer latex for ultraviolet absorption on different substrates
US6194330B1 (en) 1998-07-31 2001-02-27 Milliken & Company Polymer latex for ultraviolet absorbtion on fabric
US6482757B2 (en) 1998-07-31 2002-11-19 Milliken & Company Polymer latex for ultraviolet absorption on different substrates
US6180178B1 (en) 1998-10-22 2001-01-30 Milliken & Company Method of producing support garments by applying polyurethane coatings to specific areas of fabric
US6263707B1 (en) 1999-09-20 2001-07-24 Milliken & Company Opaque heat-moldable circular knit support fabrics having very high spandex content
US6770581B1 (en) 2000-03-17 2004-08-03 Milliken & Company Absorbent fabrics, products, and methods
US6774067B2 (en) 2000-03-17 2004-08-10 Milliken & Company Mat and method of manufacturing a mat
US6584668B2 (en) 2000-06-02 2003-07-01 Milliken & Company Method of manufacturing yarns and fabrics having a wash-durable non-electrically conductive topically applied metal-based finish
US20030200613A1 (en) * 2000-06-02 2003-10-30 Green David E. Topical incorporation of solid antimicrobial compounds on yarn surfaces through high pressure methods
US6640371B2 (en) 2000-06-02 2003-11-04 Milliken & Company Topical incorporation of solid antimicrobial compounds on yarn surfaces through high pressure
US20040224587A1 (en) * 2002-12-17 2004-11-11 Hayes Heather J. Fluorochemical-containing textile finishes that exhibit wash-durable soil release and moisture wicking properties
US7012033B2 (en) 2002-12-17 2006-03-14 Milliken And Company Fluorochemical-containing textile finishes that exhibit wash-durable soil release and moisture wicking properties
US20060101585A1 (en) * 2002-12-17 2006-05-18 Hayes Heather J Fluorochemical-containing textile finishes that exhibit wash-durable soil release and moisture wicking properties
US20070050912A1 (en) * 2005-09-02 2007-03-08 Materniak Joyce M Reduction of turmeric and iodine staining
US20090246258A1 (en) * 2008-03-28 2009-10-01 Piyush Shukla Antimicrobial and odor adsorbing textile

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