US2725308A - Composition for and treatment of textile materials - Google Patents
Composition for and treatment of textile materials Download PDFInfo
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- US2725308A US2725308A US339487A US33948753A US2725308A US 2725308 A US2725308 A US 2725308A US 339487 A US339487 A US 339487A US 33948753 A US33948753 A US 33948753A US 2725308 A US2725308 A US 2725308A
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
- D06M15/423—Amino-aldehyde resins
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
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- Y—GENERAL 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/3188—Next to cellulosic
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- Y—GENERAL 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/3188—Next to cellulosic
- Y10T428/31884—Regenerated or modified cellulose
- Y10T428/31891—Where addition polymer is an ester or halide
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- Y—GENERAL 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31942—Of aldehyde or ketone condensation product
- Y10T428/31949—Next to cellulosic
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- Y—GENERAL 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31942—Of aldehyde or ketone condensation product
- Y10T428/31949—Next to cellulosic
- Y10T428/31953—Modified or regenerated cellulose
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- Y—GENERAL 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated 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
- Y10T442/2361—Coating or impregnation improves stiffness of the fabric other than specified as a size
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- Y—GENERAL 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated 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
- Y10T442/2369—Coating or impregnation improves elasticity, bendability, resiliency, flexibility, or shape retention of the fabric
- Y10T442/2393—Coating or impregnation provides crease-resistance or wash and wear characteristics
Description
United States Patent COMPOSITION FOR AND TREATMENT OF TEXTILE MATERIALS Ralph F. Nickel-son, Marblehead, Mass., assignor to Monsanto Chemical Company, St. Louis, Mo., a corporation of Delaware No Drawing. Application February 27, 1953, Serial No. 339,487
18 Claims. (Cl. 117-65) melamine or a substantially unpolymerized dimethylol urea to textile fabrics by impregnation followed by heating at elevated temperatures, for example, 200 to 300 F. to harden and insolubilize such products in situ in the fibers of the textile fabric. It has also been proposed, heretofore, to glaze or emboss cellulose textile fabrics after they have been treated with such products, but prior to the hardening or insolubilizing step. However, the finish provided by such treatments, while'suitable in some respects, is not as crisp and stifl as is desired for certain types of fabrics. Moreover, when polymethylol melamine, methyl ethers of polymethylol melamine or dimethylol urea are applied to textile materials from acid solutions on a commercial scale, these products tend to polymerize relatively rapidly in solution to form partial polymers or colloids with the result that they tend to deposit primarily on the surface of textile fibers and yarns because of the large particle size of the product.
This often results in some stiffening of the textile material, but the stifiening is often obtained at the expense of a detrimental decrease in crush-resistance or wrinkleresistance of the textile material, and this is sometimes considered to be an unsatisfactory end result.
It has also been suggested heretofore to treat textile fabrics, particularly fabrics of vegetable origin, with an aqueous solution of a vinyl acetate-maleic anhydride copolymer and a polyhydric alcohol such as glycerine or polyvinyl alcoholand containing suffiflcient alkali to give a pH above 3.0, and then heat the fabrics at a temperature of 100 C. to 175 C. to provide a wash-resistant finish. The fabrics thus produced have a stiffened finish, but the finish is not so permanent as is oftentimes desired. Moreover, cellulose fabrics which have been treated in this manner do not have satisfactory wrinkleresistance or crush-resistance.
In accordance with the present invention, it is possible to produce a textile finish or a mechanically-modified resistance. The present invention also provides a novel composition useful for producing such improved finishes on textile materials, and which is quite stable and useful after long periods of storage at room temperatures.
It is one object of this invention to provide a process of treating textile materials, particularly textile materials composed primarily of cellulose, to produce a crisp or stiffened textile material which has satisfactory resistance to wrinkling or crushing and which retains such properties after laundering or dry cleaning.
It is-a further object of this invention to provide a process of mechanically finishing or modifying textile materials, particularly textile fabricscomposed primarily of cellulose, to produce crush or wrinkle-resistant, stiffened textile materials having a design or mechanically modified finish which is substantially durable or permanent to washing or dry cleaning.
It is a further object of this invention .to provide a crisp or stiffened, crush or wrinkle-resistant textile material, particularly a textile fabric composed primarily of cellulose, having a finish which is substantially durable to laundering or dry cleaning.
It is a further object of this invention to provide a novel composition which is quite stable in storage at normal room temperatures, and which is useful for the treatment of textile materials, particularly textilev fabrics composed primarily of cellulose, to provide a durable, crisp or stiffened and wrinkle or crush-resistant finish.
Still further objects and advantages of this invention will become apparent from the following description and the appended claims.
The present invention provides a composition comprising a water-soluble substantially tetramethylol acetylene diureine or a water-soluble substantially dimethylol hydantoin or mixtures thereof (hereinafter referred to as the methylol compound),.a water-soluble copolymer of a polymerizable compound having a single CH2=C group and an ethylenically unsaturated dicarboxylic compound copolymerizable therewith (hereinafter referred to as the water-soluble copolymer), for example, a watersoluble copolymer. of vinyl acetateand maleic anhydride, and a water-soluble polyhydric compound containing at least two hydroxyl groups (hereinafter referred to as the polyhydric compound) as, for example, a water-soluble polyvinyl alcohol.
The composition may be in the form of a dry or substantially dry mixture or in the form of a solution in which the ingredients are dissolved in a solvent, preferably water. Aqueous compositions are preferred since the methylol compound is most suitably prepared in the form of an aqueous solution and is readily mixed in such form with the water-soluble copolymer and the polyhydric compound or with aqueous solutions thereof to form aqueous compositions which are clear, infinitely dilutable with water and quite stable at ordinary room temperatures. When compositions are prepared in which an organic solvent is employed instead of water, the compositions have a relatively limited period of usefulness.
On the other hand, dryor substantially dry compositions are relatively expensive to prepare, although such compositions are quite stable at ordinary room temperatures.
The compositions of this invention may contain varying amounts of the methylol compound and the combination of the polyhydric compound and the water-soluble copolymer, and the proportion of the polyhydric compound to Water-soluble copolyrner in the combination may also be varied appreciably, depending primarily on the specific materials employed and the end use of the composition. .In general, satisfactory compositions for most purposes comprise from about 1 to 10 parts by weight of the methylol compound for each 10 to 1 parts by weight of the combination of the polyhydric compound and the water-soluble copolymer, which combination comprises from about 5 to 9 parts by weight of the watersoluble copolymer for each 5 to 1 parts by weight of the polyhydric compound. However, when thecompositions are to be used as described hereinafter for textile treatment, it is preferred to use compositions comprising from about 1 to 5 parts by weight of the methylol compound for each 2 to 1 parts by weight of the combination of the polyhydric compound and the water-soluble copolymer, which combination comprises from about 6 to 7.5 parts by weight of the water-soluble copolymer for each 4 to 2.5 parts by weight of the polyhydric compound.
The above described compositions are soluble in water per se at normal room temperatures, and the pH of the solution formed is generally below 3.0 and usually between 1.5 and 2.5 depending primarily on the particular water-soluble copolymer employed. The aqueous solutions are clear and the methylol compound therein does not polymerize appreciably at ordinary room temperatures during at least the first week of storage.
Aqueous compositions or organic solvent compositions containing the methylol compound, the water-soluble copolymer and the polyhydric compound may be employed for the production of water-resistant coat ngs or films although the aqueous compositions are particularly useful for the treatment of textile materials comprising cellulosic fibers or yarns, and are preferred for such use. The compositions may be applied, for example, to a suitable base material such as paper or wood and then dried at room temperature or at a slightly higher temperature to form continuous coatings or films which, though initially soluble in water, may be baked or heated at elevated temperatures to form a water-resistant film or coating which is substantially insoluble in water. Usually, water-resistant films or coatings are obtained by baking or heating the initial films or coatings for periods of l to 15 minutes at temperatures of 225 to 350 F., with the longer period corresponding to the lower temperature, but longer heating periods may also be used. Water-insoluble films are obtained by baking at temperatures above 250 F;, and preferably between 290 and 375 F. The water-resistant or water-insoluble films or coatings may also be formed by heating the wet films or coatings at temperatures of 225 to 375 F. without preliminary drying.
It is believed that during the baking or heating period the water-soluble copolymer reacts or cross-links with the polyhydric compound, and possibly also the methylol compound, by an esterification reaction with the splitting off of water in the case of water-soluble copolymers containing carboxyl groups or by a direct addition esterification in the case of water-soluble copolymers containing carboxylic anhydride groups to form a water-insoluble resinous material which contains at least the copolymer and the polyhydric compound in a combined state or form. Regardless of the theory involved, however, the fact remains that a water-resistant to water-insoluble resinous material is obtained.
As examples of the water-soluble copolymers which may be used in the compositions hereinbefore described may be mentioned the water-soluble copolymers of a polymerizable compound containing a single CH2=C group such as a polymerizable vinyl or vinylidene compound having a single CH2=C group as, for example, vinyl acetate, mixtures of styrene and vinyl acetate, methyl vinyl ketone, vinyl alkyl ethers such as vinyl methyl or ethyl ethers, and the like and ethylenically unsaturated aliphatic dicarboxylic acids or anhydrides containing from 4 to 8 carbon atoms as, for example, maleic anhydride, maleic acid, fumaric acid, itaconic acid, citraconic anhydride, citraconic acid and the like, and mixtures of such compounds with alkyl half esters of such acids in which the alkyl group contains from 1 to 4 carbon atoms, as, for example, mixtures of maleic anhydride and methyl acid maleate. copolymer is meant a copolymer which dissolves in water per se with agitation in concentrations of at least By water-soluble 3% by weight at a temperature of F. Of the copolymers described above the water-soluble copolymers of vinyl acetate and maleic anhydride or the watersoluble copolymers of vinyl acetate, maleic anhydride and alkyl half esters of maleic acid in which the alkyl group contains from 1 to 4 carbon atoms, particularly methyl acid maleate, are preferred. In the preparation of highly water-resistant or water-insoluble coatings or textile finishes, it is desirable to employ water-soluble copolymers which have a molecular weight above 500, and preferably above 1000.
The above copolymers may be prepared by well-known polymerization procedures. For example, they may suitably be prepared by mass polymerization of the monomers in the presence of a per-oxy polymerization catalyst such as benzoyl peroxide using heat or ultra-violet radiation, or both, to start and complete the polymerization process. The water-soluble copolymer is usually obtained in such cases as a solid mass which may be comminuted or ground to form small particles so that the material will dissolve readily in water;
As examples of water-soluble polyhydric compounds containing at least two hydroxyl groups which may be used in the compositions of this invention may be mentioned glycerine, diethylene glycol, ethylene glycol, sorbitol, mannitol, pentaerythritol, water-soluble or waterdispersible forms of starch and the like, and water-soluble polymeric materials containing at least two hydroxyl groups such as polyvinyl alcohol, water-soluble or water dispersible partially hydrolyzed polyvinyl acetates, preferably those in which at least 30% of the acetate groups have been hydrolyzed, water-soluble partially etherified polyvinyl alcohols, water-soluble partially' esterified polyvinyl alcohols and the like. The polyhydric compound preferably should consist of carbon atoms linked together by carbon to carbon bonds and having only hydrogen and hydroxyl groups attached to such carbon atoms, or preferably should have a molecular weight above 500, or preferably should contain at least 6 hydroxyl groups, or have all of these characteristics. Of the various polyhydric compounds which may be used polyvinyl alcohol provides a superior coating or finish, as compared to other polyhydric alcohols, in so far as permanence and cost are concerned, and, hence, the polyvinyl alcohol is preferred over other polyhydric compounds.
The methylol compound used in the aqueous compositions'of this invention should be substantially completely methylolated. Thus, in the case of the methylolated acetylene dilureine, the compound should contain about 3.5 to 4 mols of combined formaldehyde per mol of acetylene diureine, while in the case of the methylolated hydantoin, the compound should contain about 1.8 to 2 mols of combined formaldehyde per mol of hydantoin. If theamount of combined formaldehyde is appreciably below 4.0 mols in the case of the methylolated acetylene diureine or appreciably below 2.0 mols in the case of the methylolated hydantoin, the product tends to polymerize in the composition to a colloidal state and finally polymerizes to such an extent that it precipitates from solution. On the other hand, if the acetylene diureine or hydantoin is fully methylolated or substantially fully methylolated, the resulting methylol compound dissolves in the composition and does not polymerize to-any appreciable extent at normal room temperatures but remains in a monomeric or unpolymerized condition for considerable periods of time and is thus able to penetrate into the body of fibrous materials without depositing to any appreciable extent on the surface ofsuch materials.
The methylol compounds are suitably prepared by contacting acetylene diureine or hydantoin or mixtures thereof with an amount of formaldehyde or paraformaldehyde sufficient to completely or substantially completely methylolate such compounds, in an alkaline aqueous solution, preferably at a pH of about 7.5 to 8.5, until a solution of the desired methylol compound is obtained.
'5 The amount of formaldehyde employed is about 4 mols or more in the case of acetylene diureine and about 2 mols or more in the case of hydantoin. This addition reaction may be carried out at room temperature or at slightly elevated temperatures, for example, 30 to 70 C. The acetylene diureine uesd in preparing the methylol compound is also known as glycoluril and has the structural formula:
l H O Ba kan-NJ HN'(l11N-H The hydantoin used in preparing the methylol compound is also known as glycolylurea and has the structural formula: I
The aqueous compositions or solutions containing the water-soluble copolymer, the polyhydric compound and the methylol compound are especially useful for the treatment of textile materials, particularly textile materials containing cellulose fibers or yarns, to impart a durable, stiffened, crease-resistant finish thereto. The textile treating process of this invention is carried out, in general, by applying an aqueous solution having a pH below 3.0, preferably between about 1.5 and 2.8, of the water-soluble copolymer, the polyhydric compound and the methylol compound and, preferably, a curing catalyst to a textile material such as a cotton or regenerated cellulose fabric as by dipping, spraying or immersion, after which the fabric is dried or partially dried and then heated until a water-insoluble resin or resinous material is formed on the textile material. The baking or heating temperatures and times hereinbefore described may be used and the temperature used should be below the temperatureat which the textile material is damaged by heat, The textile material thus obtained has a permanent or substantially permanentor durable stiffened finish which is highly' resistant to removal by normal washing or launderings in aqueous soap or detergent solutions or by dry cleaning, and the finish does not pick up detrimental amounts of chlorine from bleaching solutions. This finish is, materially more permanent than finishes prepared by the use of similar solutions, but which have a pH above 3.0. The treated textile material is also res'istant to crushing or wrinkling. In order to obtain a textile material having optimum wrinkle-resistance or crush-resistance, it is necessary to treat the fabric before the heating or baking step with a catalyst which is capable of releasing a strong acid during the heating or baking step. This is suitably accomplished by adding the catalyst to the solutions applied to the textile material. The amounts of catalyst used may be varied considerably and satisfactory results are obtained in most cases by using from about 1 to 15% by weight of the catalyst, based on the weight of the methylol compound employed.
It is believed that during the baking or heating step i the water-soluble copolymer and the polyhydric comprimary mono-amines such as ethyl amine, propyl amine and the like, salts of hydrochloric or phosphoric acid and a secondary amine as, for example, an alkyl secondary mono-amine such as diethyl amine, dipropyl amine and the like and salts of hydrochloric or phosphoric acid and a hydroxy primary or secondary amine as, for example, an aliphatic primary or secondary mono-amine containing 1 to 4 hydroxyl groups such as mono-ethanolamine, isopropanolamine, l-amino-Z-methyl propanol-Z, 4-methyl-4- amino pentanol-2, diethanolamine, N-methyl, N-ethanol amine, l -ethyl, N-ethanol amine, N-dipropanediol 1-3 amine and the like. Salts of sulfuric acid and the above described amines may be used, instead of the salts of hydrochloric or phosphoric acid. However, sulfuric acid formed from such salts and remaining in the textile materials, particularly cellulose materials, tends to tender or weaken such materials, during the heating or baking step. Consequently, catalysts consisting of salts of sulfuric acid are the least desirable for use in the textile treating processes of this invention.
In general, some wrinkle-resistance and stiffening or crispening effect is obtained on the textile material when as little as 2.5% by weight of the methylol compound and 0.25% by weight of the combination of the watersoluble copoymer and the polyhydric compound, based on the dry textile material, are applied, although better results are obtained by applying at least 3% by weight of the methylol compound and at least 1.5% by weight of the combination of the water-soluble copolymer and the polyhydric compound. Considerably larger amounts of the methylol compound and the combination of the water-soluble copolymer and the polyhydric compound may be applied to the textile material, for example, as much as 15% by weight of the methylol compound and 15 or 20% by weight of the combination of the watersoluble copolymer and the polyhydric compound, it being also understood, of course, that the larger amounts of the methylol compound may be used with the small amounts of the combination of the water-soluble copolymer and the polyhydric compound and vice versa. However, for most purposes, it is not necessary to apply more than 10% by weight of the methylol compound and 5% by weight of the combination of the water-soluble copolymer and the polyhydric compound, based on the dry textile material. By increasing the amount of the methylol compound applied from 2.5 to 10% the crush or wrinkle-resistance of the textile material is increased. The above described amounts are readily applied to textile materials from an aqueous solution containing from 2.5 to 15% by weight of the methylol compound and from 0.25 to 20% by weight of the combination of the water-soluble copolymer and the polyhydric compound and by adjustment of the concentration of these ingredients within such range and with removal of excess solution from the textile material as by squeezing, centrifuging, padding or the like.
The finish produced on the textile material may be modified as to appearance, softness or other properties to some extent, if desired, by the incorporation of other materials in the aqueous solution which is applied to the textile material. For example, it is possible to incorporate film-forming materials which are soluble in water at a pH below 3.0 as, for example, gelatin and water-soluble forms of starch.
Other materials or additives may be incorporated in the treating solution as, for example, delustering agents such as titanium dioxide, colloidal silica, water-insoluble metallic silicates, talc and diatomaceous earth or the like; and also thickening agents such as gum tragacanth, hydrolyzed starch, alginic acid, hydroxy methyl cellulose, hydroxy ethyl cellulose, gelatin or the like. Normally, the delustering agents are used in amounts below 15% by weight, based on the solids in the solution, whereas the thickening agents are employed in amounts of about 0.5
to 5% by weight of the total composition.
It has presently been found that a substantially permanent or durable, wrinkle-resistant, mechanical finish may be imparted to a textile material, particularly (and preferably) a textile fabric composed primarily of cellulose such as a cotton or regenerated cellulose fabric, by first applying the aqueous solutions having a pH below 3.0, preferably between 1.5 and 2.5, of the methylol compound and the combination of the water-soluble copolymer and the polyhydric compound, and preferably a catalyst, or the various modifications of such solutions, hereinbefore described, to the textile material. The textile material is next partially dried, preferably to a moisture content of about to 70% by weight, based on the dry textile material, and is then subjected to a mechanical finishing operation such as calendering, glazing, pleating, crimping, embossing or Schreinering or the like to change the form and relative disposition of the textile fibers or yarns in the textile material and thus to alter the surface texture of the textile material. Thereafter, the textile material is heated or baked, preferably at a temperature above 250 F. but below the temperature at which the textile is damaged by heat, until a substantially water-insoluble resin finish is formed on the textile material. This baking or heating step sets the mechanically imparted or modified finish so that the finish remains on the textile material and is substantially permanent to washing and dry cleaning. The permanence or durability of the finish depends primarily on the baking or heating temperatures used, the duration of heating, the specific water-soluble copolymer and polyhydric compound employed and the relative amounts of the water-soluble copolymer and polyhydric compound applied. In carrying out the above described process it is preferred to employ a mechanical finishing operation in which heat and pressure are applied to the textile material, or to employ heat after mechanical finishing to set the finish on the textile material.
In those instances where a glazed or smooth calendered finish is desired, the textile material may be glazed or smooth calendered before or after the heating or baking step. However, best results are obtained by first applying the solution, partially drying, glazing or smooth calendering and then baking or heating to set the finish, and this procedure is preferred.
When the mechanical finishing is carried out so as to produce a permanent impression, pattern or design on the textile material, this is suitably accomplished by means of heated rolls which have the desired impression, design or pattern engraved thereon, or by means of engraved platens or the like.
It has been found desirable in the textile treating proc esses of this invention to immerse the textile material, after the formation of the water-resistant or water-insoluble resin thereon and after the mechanical finishing, if the latter procedure is used, in an aqueous solution containing alkali-metal or ionizable metal salts such as sodium carbonate, sodium bicarbonate, sodium phosphate, sodium borate, sodium chloride or the corresponding potassium or lithium compounds, and calcium chloride or barium chloride or the like. This treatment may be carried out by agitating the solution, and the solution used may contain conventional detergents, if desired. The foregoing treatment has certain advantages, but is not essential for the production of a substantially permanent'or durable, wrinkle-resistant, stiffened finish.
in carrying out the embodiment of this invention in which the textile material is mechanically finished, the proportions of the ingredients employed in the aqueous treating solution may be varied to some extent depending on the particular effect or hand desired. In general, the concentration of the solution and the pick up of the solution by the textile material are adjusted so as to apply about 2.5 to 15% by weight of the methylol compound and from about 1.5 to 15% by weight of the combination of the water-soluble copolymer and the polyhydric compound, based on the dry textile material. However, in
most instances excellent results are obtained by applying about 3 to 10% by weight of the methylol compound and from about 1.5 to 5% by weight of the combination of the water-soluble copolymer and the polyhydric compound, based on the dry textile material, and the application of such amounts if preferred. To accomplish this, it is possible to employ aqueous solutions containing substantially the same amounts of the methylol compound and the combination of the water-soluble copolymer and polyhydric compound as it is desired to apply to the textile material. The modifying agents such as, for example, the delustering agents etc. may be incorporated in the treating solution in the proportions hereinbefore described.
The mechanically finished textile materials obtained in accordance with the processes hereinbefore described have a permanent or durable wrinkle-resistant finish which is materially more crisp or stiff and less chlorine retentive than the finishes heretofore produced by the use of watersoluble urea-formaldehyde or melamine-formaldehyde condensation products per se.
A further understanding of the compositions, processes and textile products of this invention will be obtained from the following specific examples which are intended to illustrate the invention but not to limit the scope thereof, parts and percentages being by weight unless otherwise specified.
Example I Six parts of a finely divided, water-soluble copolymer of 1 mol of vinyl acetate, 0.8 mol of maleic anhydride and 0.2 mol of methyl acid maleate and three parts of finely divided low viscosity polyvinyl alcohol were first dissolved in 90 parts of water with stirring. After a clear solution was obtained, 27 parts of a slightly alkaline solution containing 50% by weight of tetramethylol acetylene diureine were added with stirring until a homogeneous solution was obtained. This solution had a pH of about 2.1 and remained clear and stable for a period of at least one week at a temperature of F. The solution, as initially prepared, was next diluted with water until it contained 3% of tetramethylol acetylene diureine, after which 5% of a 35% aqueous solution of Z-amino-Z-methyl propanol-l hydrochloride, based on the tetramethylol acetylene diureine, was added as a catalyst. The resulting solution, which was clear and stable for a considerable period of time at room temperature, was then employed for treating a textile material as described below.
A piece of x 80 cotton fabric was immersed in the composition prepared as described immediately above until it was thoroughly wetted out with the composition, after which the fabric was passed between squeeze rolls to obtain a pick up of 80% of the solution, based on the dry textile material, thus depositing about 4% total solids, based on the dry textile material, of which about 2.4% consisted of tetramethylol acetylene diureine. The fabric was next partially dried until. it contained about 55% moisture and was then embossed by pressing it between two platens having an engraved pattern thereon. The top platen was at a temperature of 350 F. and was forced against the bottom platen using a pressure of about 280 pounds per square inch for a period of 5 seconds. The embossed fabric was then heated at 300 F. until a waterinsoluble resinous material was formed on the textile material. The resulting fabric was not only deeply embossed but was also considerably stiffer or crisper and more wrinkle-resistant than the untreated fabric and retained such properties and the embossed design after a number of standard cotton washes or dry cleanings. The fabric did not pick up detrimental amounts of chlorine from bleaching solutions.
Example 11 trode) and containing 6% tetramethylol. acetylene diureine, 1.34% of a water-soluble copolymer of 1 mol of vinyl acetate, 0.8 mol of maleic anhydride and 0.2 mol of methyl acid maleate, 0.66% of low viscosity polyvinyl alcohol and 1.75%, based on the tetramethylol acetylene diureine, of Z-amino-Z-methyl propanol-l hydrochloride as a catalyst, until the fabric was thoroughly saturated with the solution. The fabric was then passed between squeeze rolls adjusted to deposit 5% of tetramethylol acetylene diureine, 1.12% of the copolymer and 0.58% of polyvinyl alcohol, based on the dry fabric. The fabric was next dried for 5 minutes at 200 F. and finally heated for 5 minutes at 300 F. to form a Water-insoluble resinous material on the fabric.
One half of the fabric was refinished by washing it for ten minutes in an aqueous solution of decyl benzene sodium sulfonate, after which the fabric was rinsed twice with water at 100 F. for periods of minutes each and then dried. This fabric had a relative stiffness of 3.2 and a relative wrinkle-resistance of 121 degrees.
The other half of the fabric was given a standard cotton wash in an aqueous solution containing equal amounts of decyl benzene sodium sulfonate and tetra sodium pyrophosphate for a period of 45 minutes at 200 F., after which the fabric was rinsed with water at 140 F. for 5 minutes, rinsed again with water at 140 F. for 10 minutes and finally dried. This fabric had a relative stiffness of 2.9 and a relative wrinkle-resistance of 118 degrees.
The untreated fabric had a relative stiffness of 2.3 and a relative wrinkle-resistance of 95 degrees.
The above results indicate that the treated fabric was significantly stiffer and more wrinkle-resistant than the untreated fabric. These differences were retained after launderings and dry cleanings.
In this example and in Examples III and IV, the relative stiffness and wrinkle-resistance of the fabric was measured after the fabrics had been conditioned for 24 hours at a relative humidity of 65% and at a temperature of 70 F. The relative stiffness was measured by means of a Gurley R. D. stiffness tester of the type described in'the patent to Ralph A. Masters, No. 2,092,609, in accordance with the procedure described in such patent. The result given represents the average of 10 determinations, 5 of which were made in the warp direction and 5 of which were made in the filling direction of the fabric. The relative wrinkle-resistance was measured using the testing device and procedure described on pages 155 and 156 of the Technical Manual and Year Book of the American Association of Textile Chemists and Colorists, Volume 28 (1952).
Example III v A piece of 80 x 80 cotton fabric was treated using theprocedure described in the first paragraph of Example II with the exception that the solution employed contained 6% of dimethylol hydantoin instead of 6% tetramethylol acetylene diureine. The treated fabric had substantially the same relative stiffness and relative crushresistance, after refinishing or a standard cotton wash,
.as the fabric obtained by the procedure of Example II.
Example I V A piece of 80 x 80 cotton fabric was immersed in an aqueous solution having a pH of about 1.9. (glass elecacetylene diureine, of 2-amino-2-methyl propanol-l hydrochloride as a catalyst for the tetramethylol acetylene diureine, until the fabric was thoroughly saturated with the solution. The fabric was then passed between squeeze rolls adjusted to deposit 3.4% of tetramethylol acetylene diureine, 2.24% of the copolymer and 1.16% of the polyvinyl alcohol, based on the dry fabric. The fabric Was '10 next dried for 5 minutes at 200 F. and finally heated for 5 minutes at 300 F. to form a water-insoluble resinous material on the fabric.
One half of the fabric was refinished by washing it for 10 minutes in an aqueous solution of decyl benzene sodium sulfonate, after which the fabric was rinsed twice with water at F. for periods of 10 minutes each and then dried. This fabric had a relative stiffness of 5.5 and a relative wrinkle-resistance of 102 degrees.
The other half of the fabric was given a standard cotton wash in an aqueous solution containing equal amounts of decyl benzene sodium sulfonate and tetra sodium pyro phosphate for a period of 45 minutes at 200 F., after which the fabric was rinsed with water at F. for 5 minutes, rinsed again with water at 140 F. for 10 minutes and finally dried. This fabric had a relative stiffness of 4.5 and a relative wrinkle-resistance of 101 degrees.
The untreated cotton fabric had a relative stiifness of 2.3 and a relative wrinkle-resistance of 95 degrees.
These results indicate that the treated fabric is materially stiffer and significantly more wrinkle-resistant than the untreated fabric. These differences are retained after launderings and dry cleanings.
Although the foregoing examples illustrate the treatment of woven cotton fabrics, it is to be understood that the processes of this invention are also applicable to the treatment of fibers, including natural and staple fibers, yarns or filarnents and knitted fabrics. For example, the compositions of this invention may be used to impart a durable, crisp or stiffened, wrinkle-resistant finish to fibers or yarns which are then formed or manufactured into fabrics, or cellulosic fibers and yarns may be treated and formed into fabrics which are then mechanically finished as hereinbefore described and finally heated or baked. The processes of this invention which relate to the production of a durable, stiffened, wrinkle-resistant finish per se are applicable to a wide variety of natural and synthetic textile materials including animal textile materials such as wool, camels hair and the like; natural cellulose textile materials such as cotton, linen, flax and the like; and synthetic textile materials such as nylon, regenerated cellulose, cellulose derivatives such as cellulose acetate and the like. However, such processes are particularly suitable for the treatment of textile materials which normally have poor wrinkle-resistance such as natural cellulose or regenerated cellulose textile materials in order to improve the wrinkle-resistance of such materials. The processes of this invention which relate to the production of mechanically modified finishes are primarily applicable to the treatment of fabrics composed primarily of cellulosic textile materials such as natural cellulose, regenerated cellulose or cellulose derivatives as, for example, cellulose acetate, preferably fabrics composed primarily of cotton and/or regenerated cellulose.
What is claimed is:
1. A stable composition of matter comprising an aqueous solution of (l) a substance selected from the group consisting of methylolacetylene diureine containing from 3.5 to 4 mols of combined formaldehyde per mol of aceylene diureine, methylol hydantoin containing from 1.8 to 2 mols of combined formaldehyde per mol of hydantoin and mixtures thereof, (2) a water-soluble polyhydric compound consisting of carbon, oxygen and hydrogen atoms and (3) a water-soluble copolymer of a compound selected from the group consisting of ethylenically unsaturated aliphatic dicarboxylic acidsand anhydrides con- 3.5 to 4 mols of combined formaldehyde per mol of acetylene diureine, methylol hydantoin containing from 1.8 to 2 mols of combined formaldehyde per mol of hydantoin and mixtures thereof, (2) a water-soluble polyhydric compound consisting of carbon, oxygen and hydrogen atoms and (3) a water-soluble copolymer of a compound selected from the group consisting of ethylenically unsaturated aliphatic dicarboxylic acids and anhydrides containing from 4 to 8 carbon atoms and mixtures of said anhydrides and acids with alkyl half esters of said acids in which the alkyl group contains from 1 to 4 carbon atoms and a substance copolymerizable therewith selected from the group consisting of polymerizable vinyl and vinylidene compounds having a single CHz=C group, said aqueous solution having a pH below 3.0 and containing from 10 to 1 parts by weight of (1) for each 1 to 10 parts by weight (2) and (3), said copolymer being present in amounts of from to 9 parts by weight for each 5 to 1 parts by weight of said polyhydric compound.
3. A composition as in claim 2, but further characterized in that (2) is a water-soluble polyvinyl alcohol and (3) is a water-soluble copolymer of vinyl acetate and maleic anhydride.
4. A composition as in claim 2, but further characterized in that (2) is a water-soluble polyvinyl alcohol and (3) is a water-soluble copolymer of vinyl acetate, maleic anhydride and an alkyl half ester of maleic acid in which the alkyl group contains from 1 to 4 carbon atoms.
5. A stable composition of matter comprising an aqueous solution of (1) tetramethylol acetylene diureine, (2) a water-soluble copolymer of vinyl acetate, maleic anhydride and an alkyl half ester of maleic acid in which the alkyl group contains from 1 to 4 carbon atoms and (3) a water-soluble polyhydric compound consisting of carbon atoms linked together by carbon to carbon bonds to which carbon atoms are attached only hydrogen and hydroxyl groups, said aqueous solution having a pH below 3.0 and containing from to 1 parts by weight of (1) for each 1 to 10 parts by weight of (2) and (3), said copolymer being present in amounts of 5 to 9 parts by weight for each 5 to 1 parts by weight of said polyhydric compound.
6. A composition as in claim 6, but further characterized in that the copolymer is a water-soluble copolymer of vinyl acetate, maleic anhydride and methyl acid maleate and said polyhydric compound is a water-soluble polyvinyl alcohol.
7. A process of finishing textile materials which comprises applying to a textile material a composition comprisin an aqueous solution'of (1) a substance selected from the group consisting of methylol acetylene diureine containing from 3.5 to 4 mols of combined formaldehyde per mol of acetylene diureine, methylol hydantoin containing from 1.8 to 2 mols of combined formaldehyde per mol of hydantoin and mixtures thereof, (2) a watersoluble polyhydric compound consisting of carbon, oxygen and hydrogen atoms and (3) a water-soluble copolymer of a compound selected from the group consisting of ethylenically unsaturated aliphatic dicarboxylic acids and anhydrides containing from 4 to 8 carbon atoms and mixtures of said anhydrides and acids with alkyl half esters of said acids in which the alkyl group contains from t to 4 carbon atoms and a substance copolymerizaole therewith selected from the group consisting of polymerizable vinyl and vinylidene compounds having a single CH2=C group, said solution having a pH below 3.0, and drying and heating the textile material until a Waterinsoluble resinous material is formed on the textile material.
8. A process as in claim 3, but further characterized in that the solution contains a catalyst for (1).
9. A process as in claim 8, but further characterized in that the water-soluble copolymer is a water-soluble copolymer of vinyl acetate and maleic anhydride.
10. A process as in claim 9, but further characterized in that the water-soluble copolymer is a water-soluble copolymer of vinyl acetate, maleic anhydride and an alkyl half ester of maleic acid in which the alkyl group contains from 1 to 4 carbon atoms.
11. A process of finishing textile materials composed primarily of cellulose which comprises applying to said textile materials a composition comprising an aqueous solution of (1) a substance selected from the group consisting of methylol acetylene diureine containing from 3.5 to 4 mols of combined formaldehyde per mol of acetylene diureine, methylol hydantoin containing from 1.8 to 2 mols of combined formaldehyde per mol of hydantoin and mixtures thereof, (2) a water-soluble polyhydric compound consisting of carbon, oxygen and hydrogen atoms and (3) a water-soluble copolymer of a. compound selected from the group consisting of ethylenically unsaturated aliphatic dicarboxylic acids and anhydrides containing from 4 to 8 carbon atoms and mixtures of said anhydrides and acids with alkyl half esters of said acids in which the alkyl group contains from 1 to 4 carbon atoms and a substance copolymerizable therewith selected from the group consisting of polymerizable vinyl and vinylidene compounds having a single CHz=C group, said solution having a pH below 3.0, partially drying said textile materials and mechanically finishing said textile materials by the application of pressure to alter the surface texture of the materials, said materials being heated at some stage of the process after partial drying until a water-insoluble resinous material is formed on the textile materials.
12. A process as in claim 11, but further characterized in that the solution also contains a catalyst for (1).
13. A process as in claim 11, but further characterized in that (l) is tetramethylol acetylene diureine, (2) is a water-soluble polyvinyl alcohol and (3) is a water-soluble copolymer of vinyl acetate and maleic anhydride, and the solution also contains a catalyst for (1).
14. A process as in claim 11, but further characterized in that (1) is tetramethylol acetylene diureine, (2) is a water-soluble polyvinyl alcohol and (3) is a watersoluble copolymer of vinyl acetate, maleic anhydride and an alkyl half ester of maleic acid in which the alkyl group contains from 1 to 4 carbon atoms, and the solution also contains a catalyst for (1).
15. A process of finishing a textile fabric composed primarily of cellulose which comprises applying to said fabric a composition comprising an aqueous solution of (1) tetramethylol acetylene diureine, (2) a water-soluble copolymer of vinyl acetate, maleic anhydride and an alkyl half ester of maleic acid in which the alkyl group contains from 1 to 4 carbon atoms, (3) a water-soluble polyhydric compound consisting of carbon, oxygen and hydrogen atoms and (4) a catalyst for 1), said solution having a pH below 3.0, partially drying said fabric, embossing said fabric and thereafter heating the fabric until a water-insoluble resinous material is formed on the fabric.
16. A process of finishing a textile fabric composed primarily of cellulose which comprises applying to said fabric a composition comprising an aqueous solution of (1) tetramethylol acetylene diureine, (2) a water-soluble polyhydric compound consisting of carbon, oxygen and hydrogen atoms, 3) a water-soluble copolymer of vinyl acetate, maleic anhydride and an alkyl half ester of maleic acid in which the alkyl group contains from 1 to 4 carbon atoms and (4) a catalyst for (1), said solution having a pH below 3.0, partially drying said fabric, calendering said fabric and thereafter heating the fabric until a water-insoluble resinous material is formed on the fabric. v
17. A textile material composed primarily of cellulose and having a stiffened, durable, wrinkle-resistant finish comprising a reaction product of cellulose and a substance selected from the group consisting of methylol acetylene diureine containing from 3.5 to 4 mols of combined formaldehyde per mol of acetylene diureine, methylol hydantoin containing from 1.8 to 2 mols of combined formaldehyde per mol of hydantoin and mixtures thereof, and a water-insoluble reaction product of (1) a water-soluble polyhydric compound consisting of carbon, oxygen and hydrogen atoms and (2) a water-soluble co polymer of a compound selected from the group consisting of ethylenically unsaturated aliphatic dicarboxylic acids and anhydrides containing from 4 to 8 carbon atoms and mixtures of said acids and anhydrides with alkyl half esters of said acids in which the alkyl group contains from 1 to 4 carbon atoms and a substance copolymerizable therewith selected from the group consisting of polymerizable vinyl and vinylidene compounds having a single CH2=C group.
References Cited in the file of this patent UNITED STATES PATENTS 2,574,114 Lehmann et a1 Nov. 6, 1951 2,602,018 Beer July 1, 1952 2,609,350 Spott Sept. 2, 1952 FOREIGN PATENTS 858,223 France May 6, 1940 898,259 France June 26, 1944
Claims (1)
11. A PROCESS OF FINISHING TEXTILE MATERIALS COMPOSED PRIMARILY OF CELLULOSE WHICH COMPRISES APPLYING TO SAID TEXTILES A COMPOSITION COMPRISING AN AQUEOUS SOLUTION OF (1) A SUBSTANCE SELECTED FROM THE GROUP CONSISTING OF METHYLOL ACETYLENE DIUREINE CONTAINING FROM 3:5 TO 4 MOLS OF COMBINED FORMALDEHYDE PER MOL OF ACETYLENE DIUREINE, METHYLOL HYDANOIN CONTAINING FROM 1.8 TO 2 MOLS OF COMBINED FORMALDEHYDE PER MOL OF HYDANTOIN AND MIXTURES THEREOF (2) A WATER-SOLUBLE POLYHYDRIC COMPOUND CONSISTING OF CARBON, OXYGEN AND HYDROGEN ATOMS AND (3) A WATER-SOLUBLE COPOLYER OF A COMPOUND SELECTED FROM THE GROUP CONSISTING OF ETHYLENICALLY UNSATURATED ALIPHATIC DICARBOXYLIC ACIDS AND ANHYDRIDES CONTAINING FROM 4 TO 8 CARBON ATOMS AND MIXTURES OF SAID ANHYDRIDES AND ACIDS WITH ALKYL HALF ESTERS OF SAID ACIDS IN WHICH THE ALKYL GROUP CONTAINS FROM 1 TO 4 CARBON ATOMS AND A SUBSTANCE COPOLYMERIZABLE THEREWITH SELECTED FROM THE GROUP CONSISITING OF POLYMERIZABLE VINLY AND VINYLADENE COMPOUNDS HAVING A SINLE CH2=CV GROUP, WITH SOLUTION HAVING A PH BELOW 3.0, PARTIALLY DRYING SAID TEXTILE MATERIALS AND MECHANICALLY FINISHING SAID TEXTILE MATERIALS BY THE APPLICATION OF PRESSURE TO ALTER THE SURFACE TEXTURE OF THE MATERIAL, SAID MATERIALS BEING HEATED AT SOME STAGE OF THE PROCESS AFTER PARTIAL DRYING UNTIL A WATER-INSOLUBLE RESINOUS MATERIAL IS FORMED ON THE TEXTILE MATERIAL.
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US339487A US2725308A (en) | 1953-02-27 | 1953-02-27 | Composition for and treatment of textile materials |
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US2943949A (en) * | 1957-10-23 | 1960-07-05 | Congoleum Nairn Inc | Decorative plastic surface covering and process therefor |
US2977246A (en) * | 1958-06-03 | 1961-03-28 | Du Pont | Process for coating film |
US2987421A (en) * | 1955-09-19 | 1961-06-06 | Goodrich Co B F | Composition for treating textile materials, method, and article produced thereby |
US3071430A (en) * | 1957-03-11 | 1963-01-01 | Bleachers Ass Ltd | Treatment of fibrous materials |
US3262897A (en) * | 1960-06-27 | 1966-07-26 | Catalin Corp | Thermosetting resins modified with glycolic ester derivatives and method of producing the same |
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 |
US3532769A (en) * | 1966-03-28 | 1970-10-06 | Reichhold Chemicals Inc | Heat-hardenable binders for coating compositions |
US3632422A (en) * | 1969-12-04 | 1972-01-04 | Burlington Industries Inc | Textile fabric having soil release finish and method of making same |
US4118437A (en) * | 1976-04-08 | 1978-10-03 | American Cyanamid Company | Cross linkable powder coating compositions |
US4448929A (en) * | 1981-08-26 | 1984-05-15 | Stauffer Chemical Company | Encapsulation process |
US4456569A (en) * | 1982-06-01 | 1984-06-26 | Stauffer Chemical Company | Encapsulation process |
US20040039195A1 (en) * | 1999-10-21 | 2004-02-26 | Pohang University Of Science And Technology | Cucurbituril derivatives, their preparation method and uses |
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US2609350A (en) * | 1946-12-21 | 1952-09-02 | Gen Aniline & Film Corp | Textile finishing agent |
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Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
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US2987421A (en) * | 1955-09-19 | 1961-06-06 | Goodrich Co B F | Composition for treating textile materials, method, and article produced thereby |
US3071430A (en) * | 1957-03-11 | 1963-01-01 | Bleachers Ass Ltd | Treatment of fibrous materials |
US2943949A (en) * | 1957-10-23 | 1960-07-05 | Congoleum Nairn Inc | Decorative plastic surface covering and process therefor |
US2977246A (en) * | 1958-06-03 | 1961-03-28 | Du Pont | Process for coating film |
US3262897A (en) * | 1960-06-27 | 1966-07-26 | Catalin Corp | Thermosetting resins modified with glycolic ester derivatives and method of producing the same |
US3532767A (en) * | 1966-03-28 | 1970-10-06 | Reichhold Chemicals Inc | Heat-hardenable binders for coating compositions |
US3532769A (en) * | 1966-03-28 | 1970-10-06 | Reichhold Chemicals Inc | Heat-hardenable binders for coating compositions |
US3532770A (en) * | 1966-03-28 | 1970-10-06 | Reichhold Chemicals Inc | Heat-hardenable binders for coating compositions |
US3532768A (en) * | 1966-03-28 | 1970-10-06 | Reichhold Chemicals Inc | Heat-hardenable binders for coating compositions |
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US3632422A (en) * | 1969-12-04 | 1972-01-04 | Burlington Industries Inc | Textile fabric having soil release finish and method of making same |
US4118437A (en) * | 1976-04-08 | 1978-10-03 | American Cyanamid Company | Cross linkable powder coating compositions |
US4448929A (en) * | 1981-08-26 | 1984-05-15 | Stauffer Chemical Company | Encapsulation process |
US4456569A (en) * | 1982-06-01 | 1984-06-26 | Stauffer Chemical Company | Encapsulation process |
US20040039195A1 (en) * | 1999-10-21 | 2004-02-26 | Pohang University Of Science And Technology | Cucurbituril derivatives, their preparation method and uses |
US7160466B2 (en) * | 1999-10-21 | 2007-01-09 | Pohang University Of Science And Technology Foundation | Uses of cucurbituril devices |
WO2009151682A1 (en) | 2008-03-12 | 2009-12-17 | Dewal Industries | Venting liner and method |
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