US2950553A - Method of producing wrinkle resistant garments and other manufactured articles of cotton-containing fabrics - Google Patents

Method of producing wrinkle resistant garments and other manufactured articles of cotton-containing fabrics Download PDF

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US2950553A
US2950553A US63459057A US2950553A US 2950553 A US2950553 A US 2950553A US 63459057 A US63459057 A US 63459057A US 2950553 A US2950553 A US 2950553A
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fabric
cotton
condensate
garments
ironing
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Melvin D Hurwitz
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Rohm and Haas Company
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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
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423Amino-aldehyde resins
    • 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
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39Aldehyde resins; Ketone resins; Polyacetals

Description

2,950,553? Patented Aug. 30, 1960 WTHOD OF PRODUCING WRINKLE RESISTANT GARMENTS AND OTHER MANUFACTURED ARTICLES OF COTTON-CONTAINING FABRICS Melvin D. Hurwitz, Hnntingdon Valley, Pa., assignor to Rohm & Haas Company, Philadelphia, Pa., :1 corporation of Delaware No Drawing. Filed Jan. 16, 1957, Ser. No. 634,590

3 Claims. (Cl. 38-144) It is known to apply aminoplast-types of resin-forming condensates to cotton fabrics and to cure the condensates on the fabrics to impart wash-resistant, wrinkle-resistant finishes thereon, and then to make garments, drapes, curtains, and other decorative articles therefrom. Many manufacturers of garments and other articles are still reluctant to use such treated fabrics because of the difficulties encountered in making garments therefrom. Among such difliculties are needle-cutting, by which is meant the tendency of a needle to split the fabric along sewn seams. Another is the resistance to pressing. For example, it is extremely difiicult to introduce a sharp crease into men's trousers made from certain of such crease-resistant fabrics.

it is an object of the present invention to provide a process for producing garments, curtains, drapes, or other manufactured articles of cotton-containing fabrics in which the diificulties just mentioned are avoided. Another object is to provide a process that is adapted to be employed either in a garment-manufacturing plant or in the home to make garments and other textile articles which are wrinkle-resistant and crease-proofed. Other objects and advantages of the invention will be apparent or expressly mentioned in the description following.

In its broadest aspect, the process of the present invention involves the application of a resin-forming aminoplast condensate in conjunction with a catalyst to a cotton fabric at any time before or after the making of garments or textile articles, such as drapes, curtains or the like, drying the condensate upon the fabric without appreciably curing it and then, after making the garment or other textile article, curing the condensate there on by a simple pressing or ironing.

it has been discovered that when certain catalysts are employed, the aminoplast condensates may be cured to form the wrinkle-resistant finish on the cotton fabrics stnticiently rapidly that such curing can be effected by a simple pressing or ironing operation, such as that obtained by the use of a commercial mangle or by handironing, with an ordinary electric iron or with a steam type of electric iron. These catalysts are magnesium chloride, magnesium perchlorate, zinc nitrate, zinc perchlorate, and zinc fiuoborate. From about 0.25% to about 2%, on the total weight of the treating solution, or any one of these metal salts or of a mixture thereof may be employed as the catalyst for the aminoplast condensates described hereinafter. Other catalysts that may be employed, but which have the disadvantage either that extreme care may be needed to employ a predetermined concentration to effect the crease-proofing without damage to the fabric or that longer times of ironing or repeated ironings are generally required, include ammonium chloride, ammonium diacid phosphate, citric acid, tartaric acid, and hydrochloric or other acid salts of a hydroxyaliphatic amine including monoethanolamine, diethanolamine, 2-methyl-2-amino-l-propanol, 2-methyl2- amino 1,3 propandiol, tris(hydroxymethyl)aminomethane, Z-pheHyl-Z-amino-l-propanol, Z-methyl-Z-amino-lpentanol, 2-aminobutanol, triethanolamine, 2-amino-2- ethyl-l-butanoh Mixtures of catalysts, such as mixtures of the metal salts mentioned above, with the amine hydrochlorides may be used and they are as effective practically as the use of the metal salts alone provided the amount of metal salt is in the range of 0.25% to about 2% of the total treating solution.

Unless otherwise stated herein, the term cotton fabric is intended to include not only fabrics composed entirely of cotton fibers but also those that contain at least 40% by weight of cotton in conjunction with other fibers or continuous filaments. Thus, the fabric may be formed of a blend of cotton with one or more of any of the following fibers or filaments: viscose rayon, cuprammonium cellulose rayon, cellulose acetate, polyethylene terephthalate, nylon, wool, silk, linen, polymers of at least acrylonitrile, such as those available commercially under the tradenames Orlon and Acrilan, polyethylene, and so on. The fabric construction may be of a wide variety, loosely-woven fabrics with large loosely-twisted yarns in symmetrical weaves yielding the best results. Others include Oxford cloth, percales, such as 80 by 80 denims, twills, and so on.

The aminoplast condensates which are rapidly cured by the above catalysts are the resin-forming condensates of formaldehyde or equivalent materials, such as paraformaldehyde, with urea, N,N'-ethyleneurea, N,N'-trimethyleneurea, aminotriazines, such as melamine and substituted melamines, and tetrahydro-s-triazones of Formula I 1 nocrn-N N-onion where R is selected from the group consisting of 2-hydroxyethyl, Z-methyl-Z-hydroxyethyl, and alkyl groups having 1 to 4 carbon atoms.

Besides utilizing the water-soluble methylol derivatives of the above-nitrogen-containing compounds, there may be used the water-soluble ethers thereof with methyl alcohol, ethyl alcohol, and so on.

The concentration of the aminoplast resin-forming condensate in the treating bath may be within the range of 1 to 10% by weight, depending upon the particular fabric construction and the extent of crease-resistance desired.

While the aminoplast condensate and the metal salt are essential components of the aqueous treating bath, the treating composition may include other materials to improve other characteristics such as to modify the hand. Among these other components, there may be thermoplastic acrylic polymers either of Water-soluble character or in the form of an aqueous dispersion, such as is obtained by emulsion polymerization. This type of material enhances the crease-resistance obtained by the use of the aminoplast condensate.

Examples of the thermoplastic polymer include the water-insoluble emulsion copolymers of about 0.5 to 8% by weight of arcylic acid, methacrylic acid, and itaconic acid with one or more esters of acrylic acid or methacrylic acid with monohydric alcohols having from 1 to 12 carbon atoms, such as ethanol, methanol, butanol, and so on. There may be used up to 20% concentration of this material in the treating bath.

Another optional material that may be included for the purpose of building the hand and imparting a crisp hand includes a water-soluble polymeric material, such as polyvinyl alcohol, partially saponified polyvinyl acetate, water-soluble or alkali-soluble water-insoluble hydroxyethyl cellulose, starch, ethylene oxide modified starches, carboxymethyl cellulose and so on. The amount of this material may be up to 10% concentration in the solution.

Another material that may be included is a lubricant. This may be of the silicone-type, higher fatty acid ester or amide types, such as stearamide, stearic acid, stearin, methyl stearate, or salts of the fatty acids, such as sodium oleate, sodium stearate, emulsified waxes, or mineral oils and quaternary ammonium compounds. Examples of the quaternary ammonium compounds which are suitable are those having a long chain hydrocarbon group, such as stearyl pyridinium chloride, octadecyl oxyniethylpyridinium chloride, and the various quarternary ammonium salts described in US. Patent 2,351,581. The lubricants also tend to impart water-repellency to the garments or other articles in many instances. Up to of the lubricant may be contained in the treating bath.

Another material that may be included in the bath is a penetrant or wetting agent, preferably of non-ionic type. Examples include alkylphenoxypolyethoxyethanols having alkyl groups of about seven to eighteen carbon atoms and 6 to 60 or more oxyethylene units, such as heptylphenoxypolyethoxyethanols, octylphenoxypolyethoxyethanols, methyloctylphenoxypolyethoxyethanols, nonylphenoxypolyethoxyethanols, dodecylphenoxypolyethoxyethanols, and the like; polyethoxyethanol derivatives of methylene linked alkyl phenols; sulfur-containing agents such as those made by condensing 6 to 60 or more moles of ethylene oxide with nonyl, dodecyl, tetradecyl, t-dodecyl, and the like mercaptans or with alkylthiophenols having alkyl groups of six to fifteen carbon atoms; ethylene oxide derivatives of long-chained carboxylic acids, such as lauric, myristic, palmitic, oleic, and the like or mixtures of acids such as found in tall oil containing 6 to 60 oxyethylene units per molecule; analogous ethylene oxide condensates of long-chained alcohols, such as octyl, decyl, lauryl, or cetyl alcohols, ethylene oxide, derivatives of etherified or esterified polyhydroxy compounds having a hydrophobic hydrocarbon chain, such as sorbitan monostearate containing 6 to 60 oxyethylene units, etc.; block copolymers of ethylene oxide and propylene oxide comprising a hydrophobic propylene oxide section combined with one or more hydrophilic ethylene oxide sections.

Various ways may be employed for treating the fabrics or garments with the solution or composition containing the catalyst and aminoplast condensate with or without the additional ingredients mentioned above. In one embodiment, the garment may be made out of the cotton fabric which may be a dyed fabric or if not the garment may be dyed and thereafter the garment may be treated with the composition either by spraying it upon the garment or preferably by dipping or immersing the garment in the bath. The immersion may be accompanied by agitation or may be repeated several times or, if desired, the garment may be squeezed while within the batch or between immersions in the bath or both. These varia tions in the treatment serve to enhance the impregnation and penetration to insure thorough and uniform distribution of the treating composition throughout the garment or other article. Thereafter the garment may be dried under conditions which do not appreciably cure the condensate. Generally, the drying is effected at a temperature of 200 F. or less, preferably at room temperature, and the temperature selected for a given case may depend upon the particular condensate and the particular catalyst employed. Centrifuging may be used to effect preliminary removal of excess liquid and any suitable drying means may be employed, such as drying ovens, through which heated air is passed, radiators and the like, provided the temperature is controlled to avoid premature curing. After drying, the garment or other article is pressed at a temperature from about 212 F. or any temperature thereabove short of a temperature at which scorching or other deterioration of the fiber is produced. Preferably, the temperature of ironing or pressing is about 275 F. to 300 F. During the ironing, care is taken to introduce whatever creasing or pleating is desired and care is taken to avoid the introduction of creases where theyare not desired. The ironing may be effected while the fabric is damp or dry. Generally, greater ease of ironing is obtained with a slightly damp condition. A second dry ironing should preferably follow a damp ironing. When ironing by hand at the normal speed, the contact of the iron is generally adequate because of the rapid cure obtained when the metal salt catalysts mentioned above are used.

Instead of applying the treating composition to the garment, it may be applied to a fabric in the fiat condition before it has been cut and converted into a garment or other textile article. Thus, the fabric may be custom treated by a textile finisher with the treating composition and dried without effecting cure thereof on the fabric. The finisher may sell the fabric to the garmentmanufacturer, who makes the garment in the normal fashion, and after completing it effects cure simply by ironing or pressing in the manner discussed hereinabove. The manufacturer of the garment in this case may be the housewife and the same procedure may be employed in the making of curtains, drapes, and so on. The treatment of the fiat fabric in this manner should follow dyeing or other finishing treatment when such dyeing and finishing, as is usual, involves treatment in an aqueous system. The reason for this is to avoid the removal of the condensate during any subsequent dyeing or finishing operation. The application of the condensate to the fiat fabric is often more convenient since conventional sizing apparatus and roll-squeegeeing apparatus may be used to effect the saturation and penetration of the fabric with the treating material.

In general, the treatment is effected on the entire area of the garment or other article but, if desired, the treating composition may be applied to local areas to obtain local effects.

The advantages of the present invention are numerous. The risk of needle-cutting during the making of garments is avoided. Likewise, there is no resistance to the pressing or ironing as would be the case when an already crease-proofed fabric or garment is ironed. With the garments or other articles made in accordance with the present invention, there is no curing 0r crease-proofing until the ironing step. This results in the introduction of better pleats or creases where they are desired and enables the custom pleating of garments either by the manufacturer of the garment or by the home tailor. The fabrics produced by the present invention require either no pressing or less frequent pressing on each wearing or washing.

The process of the present invention is useful for the production of womens blouses, skirts, and dresses, mens sport shirts, slacks, sport jackets, and also drapes, curtains and like articles. In connection with the manufacture of trousers, such as slacks, which are cut to length and then cuffed, it is possible by the process of the present invention to supply the slacks or other trousers to the retail store with a temporary crease produced by pressing during drying at a temperature at which relatively little curing or no curing occurs. Upon measurement of the length of the trousers and forming of the cuffs, the final creasing may be introduced by a simple ironing operation at a temperature of 212 F. or higher.

The following examples, in which parts and percen tages are by weight, are illustrative of the invention:

Example 1 A formulation of the following composition is prepared:

G. Dimethylol-N,N'-ethylcncurca (50% in water) 600 Emulsion polymer of ethyl :lcrylatc (50% in water)" 120 Poly(mcthoxysiloxanc) (25% in water) 80 Methylene his-diamylphenoxypolycthoxyethanol containing about 9 oxymethylene units 0.4 Zinc nitrate (35% in water) 50 Poly(vinyl alcohol) (i075 in water) 200 Water to make 4 liters.

The following garments are immersed into the above formulation:

(1) 8.5-02. cotton twill trousers (2) -02. cotton-denim sport trousers (3) 136 x 60 cotton broadcloth shirt (4) 80 x 80 cotton printcloth skirt After removal of excess liquid by centrifuging, the garments while still damp are ironed with a household steam iron. This is followed by a pressing without steam during which the iron is set between the normal positions for W001 and rayon respectively (about 375 F.). Care is taken during ironing to avoid the pressing into the garment of undesired creases or wrinkles. The ironing of the trousers is cliccted in such a way as to introduce the desired creases in both back and front of the legs thereof. In the skirt, short pleats are introduced adjacent the beltline by the ironing.

The garments thus prepared are washed in an automatic washing machine with a commercially available household laundry detergent. After draining, the garments are hung up to dry in as wrinkle-free condition as feasible. After drying. the print cloth skirt is substantially completely wrinkle-free; the sport denim trousers and broadcloth shirt had a few minor wrinkles but were suitable to be worn without further ironing; and the cotton twills showed somewhat less perfection but needed only a light ironing in a few areas to restore them to good condition for further wearings. In all cases, the pleats and creases previously pressed in remain sharp in outline. On wearing the above-described treated garments, they remain relatively free of wrinkling under the same conditions that untreated garments would become particularly wrinkled and baggy.

Example 2 A dark printed 80 by 80 cotton skirt is treated as described in Example 1 except that the dimethylol-N,N'- ethyleneurea is replaced by 560 grams of an 80% solution in water of dimethoxymethyl methylol melamine. The appearance after laundering and drying is good and the wrinkle-resistance on wearing is as good as that obtained for the corresponding type of garment treated in Example 1.

Example 3 A shirt and skirt similar to those used in Example 1 are treated in an aqueous solution containing 800 grams of dimethoxymethylurea and 35 grams of zinc perchlorate in 10 liters of water. After removing excess by centrifuging, the garments are subjected to ironing as in Example 1. The fabrics show good wrinkle-resistance during Wearing and require no ironing after washing.

Example 4 A pair of denim sport trousers, a cotton shirt and a cotton print skirt are each immersed in a solution containing 300 grams of dimethylol-N,N'-ethyleneurea and 30 grams of zinc fluoroborate in 5 liters of water. After removing excess and ironing as in Example 1, the garments are washed and dried in as wrinkle-free a condition as possible. At the completion of drying, they exhibit substantially complete freedom from wrinkles so that they may be worn without an ironing or pressing operation. As in the other garments treated by the procedurcs of the other examples above, the garments obtained herein undergo far less wrinkling and retain their shape and any desired pleats or creases far longer during normal wear than untreated garments.

Example 5 The same four types of garments as are described in Example 1 are treated in a formulation having the same composition as that described in Example 1 except that the zinc nitrate is replaced with 50 grams of a solution of magnesium chloride in Water having a concentration of 45%. Similar results are obtained. As in Example 1, the garments in which pleats and creases are introduced during the initial ironing retain their shape during wearing and need little or no ironing after Washing.

It is to be understood that changes and variations may be made without departing from the s irit and scope of the invention as defined in the appended claims.

I claim:

1. A method for producing a wrinkle-resistant textile article formed of a cotton fabric which comprises applying an aqueous dispersion containing about 1% to 10% by weight of an aminoplast resin-forming condensate and about 0.25% to about 2% by weight of a catalyst selected from the group consisting of magnesium chloride, mag-' 4 nesium perchlorate, zine nitrate, zinc perchlorate, and zinc fluoborate t0 the fabric to effect impregnation thereof, drying the impregnated fabric at a temperature not over 200 P. such that appreciable curing of the condensate is avoided, forming the fabric into an article with a seam therein, said seam being formed at a time in the period extending from a time prior to the impregnation of the fabric to a time after the drying of the impregnated fabric, and subsequently pressing the article containing the seam at a temperature of at least 212 F. to effect curing of the condensate simultaneously with the pressing.

2. A method as defined in claim 1 in which the aminoplast condensate is a water-dispcrsible condensate of formaldehyde wtih a member selected from the group consisting of urea, N,N'-cthylcneurea, N,N-trimethylcneurea, aminotriazines and tetrahydro-s-triazones of the formula where R is selected from the group consisting of 2-hydroxyethyl, 2-methyl-2-hydroxyethyl, and alkyl groups having 1 to 4 carbon atoms.

3. A method as defined in claim 1 in which portions of the fabric in the article are overlapped and the overlapped portions are subjected to the pressing whereby at least one predetermined crease is introduced into the article by the pressing.

HOCHFIII 20 References Cited in the file of this patent UNITED STATES PATENTS 2,326,605 Bass et a1 Aug. 10, 1943 2,400,016 Meyer May 7, 1946 2,526,462 Edelstein Oct. 17, 1950 2,711,971 Miller et a1 June 28, 1955 2,755,198 Stewart July 17, 1956 2,769,584 Zinamon et al. Nov. 6, 1956 2,817,568 Brown Dec. 24, 1957 2,826,500 Keim Mar. 11, 1958 OTHER REFERENCES Ellis: Chemistry of Synthetic Resins, vol. I, 1935, Reinhold Publishing Corp., pages 611 and 612.

Claims (1)

1. A METHOD FOR PRODUCING A WRINKLE-RESISTANT TEXTILE ARTICLE FORMED OF A COTTON FABRIC WHICH COMPRISES APPLYING AN AQUEOUS DISPERSING CONTAINING ABOUT 1% TO 10% BY WEIGHT OF AN AMINOPLAST RESIN-FORMING CONDENSATE AND ABOUT 0.25% TO ABOUT 2% BY WEIGHT OF A CATALYST SELECTED FROM THE GROUP CONSISTING OF MAGNESIUM CHLORIDE, MAGNESIUM PERCHLORATE, ZINC NITRATE, ZINC PERCHLORATE, AND ZINC FLUOBORATE TO THE FABRIC TO EFFECT IMPREGNATION THEREOF, DRYING THE IMPREGNATED FABRIC AT A TEMPERATURE NOT OVER 200* F. SUCH THAT APPRECIABLE CURING OF THE CONDENSATE IS AVOIDED, FORMING THE FABRIC INTO AN ARTICLE WITH A SEAM THEREIN, SAID SEAM BEING FORMED AT A TIME IN THE PERIOD EXTENDING FROM A TIME PRIOR TO THE IMPREGNATION OF THE FABRIC TO A TIME AFTER THE DRYING OF THE IMPREGNATED FABRIC, AND SUBSEQUENTLY PRESSING THE ARTICLE CONTAINING THE SEAM AT A TEMPERATURE OF AT LEAST 212* F. TO EFFECT CURING OF THE CONDENSATE SIMULTANEOUSLY WITH THE PRESSING.
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Cited By (40)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3043718A (en) * 1959-07-09 1962-07-10 Rohm & Haas Compositions, textiles treated therewith, and processes for the treatment thereof
US3094705A (en) * 1960-12-29 1963-06-25 John D Reid Method for producing a pucker-free seam in a garment
US3135710A (en) * 1960-09-22 1964-06-02 Rohm & Haas Aqueous dispersion of aminoplast and butene-2-diol-1, 4
US3138802A (en) * 1962-05-25 1964-06-30 Cotton Producers Inst Of The N Process for imparting durable creases, wrinkle resistance and shape retention to cellulosic textile articles
US3140197A (en) * 1959-04-01 1964-07-07 Heberlein & Co Ag Finished textile and method of producing same
US3173895A (en) * 1961-04-01 1965-03-16 Hoechst Ag Process for preparing hardenable condensation products from bistriazinones
US3197790A (en) * 1964-05-06 1965-08-03 Cotton Producers Inst Of The N Process for imparting durable loft and warmth to cellulosic fabrics
US3220869A (en) * 1959-03-13 1965-11-30 Basf Ag Process for improving textile fabrics
US3238166A (en) * 1961-10-10 1966-03-01 Sumitomo Chemical Co Brocess for endowing permanent dirtpreventing property and hardness to fabrics of synthetic fibers, and resin composition therefor
US3268915A (en) * 1963-04-08 1966-08-30 Koratron Company Inc Process of manufacturing press-free garment with retained creases
US3274189A (en) * 1963-04-22 1966-09-20 Dan River Mills Inc Novel compositions for treating textiles and process for making same utilizing phosphoric acid
US3301631A (en) * 1962-08-21 1967-01-31 Deering Milliken Res Corp Process of modifying cellulosic textiles with epihalohydrin-triazone reaction products
US3378397A (en) * 1964-04-09 1968-04-16 Sun Chemical Corp Highly alkylolated textile finishing composition and process for treating textile fabric therewith
US3381310A (en) * 1964-08-11 1968-05-07 Stevens & Co Inc J P Permanently creased and pleated fabrics and process for producing same
DE1268098B (en) * 1961-02-17 1968-05-16 Calico Printers Ass Ltd A method for anti-wrinkling of cellulose textiles
DE1283798B (en) * 1960-11-21 1968-11-28 Hooker Chemical Corp A process for Flammfestausruestung of cellulose-containing textile
US3425856A (en) * 1964-09-15 1969-02-04 Riegel Textile Corp Process for producing permanent creases and other desirable properties in textile fabrics
US3432862A (en) * 1966-03-04 1969-03-18 Harry H Weiler Adjustable size garment
US3434875A (en) * 1964-06-29 1969-03-25 Burlington Industries Inc Textile fabric coated with a high molecular weight methylpolysiloxane elastomer polymer
US3445277A (en) * 1964-12-22 1969-05-20 Cotton Producers Inst Differential treatment for improving the shape holding properties of cellulosic fabrics
US3458349A (en) * 1965-01-14 1969-07-29 Sumitomo Chemical Co Process for imparting wet and dry crease resistance to textile fabrics with an n-methylolate acrylamide telomer
US3473948A (en) * 1966-09-29 1969-10-21 Burlington Industries Inc Method of improving resin finished textiles
US3510249A (en) * 1966-04-06 1970-05-05 Dan River Mills Inc Precure process
US3512921A (en) * 1966-03-24 1970-05-19 Sun Chemical Corp Treatment of cellulosic textiles with 1 - substituted - 3,5 - dimethylol-2,6-dihydrotriazin-4-one
US3518043A (en) * 1965-08-17 1970-06-30 Basf Ag Hexahydropyrimidone derivatives and a method of finishing textile material
US3519381A (en) * 1966-08-22 1970-07-07 Chevron Res Method of imparting permanent crease to fabrics containing free hydroxyl groups
US3519562A (en) * 1964-04-28 1970-07-07 Procter & Gamble Textile lubricant
US3527558A (en) * 1966-01-18 1970-09-08 Burlington Industries Inc Process for treating cellulosic textiles
US3542503A (en) * 1966-06-23 1970-11-24 Us Agriculture Process for imparting wrinkle resistance and recovery properties to cotton stretch fabrics
US3731411A (en) * 1971-06-11 1973-05-08 Burlington Industries Inc Process for producing durable press textiles
US3795480A (en) * 1972-01-24 1974-03-05 Us Agriculture Process for preparing durable-press or wash-wear fabrics which can be whitened with acidic optical brighteners
US3796540A (en) * 1972-03-28 1974-03-12 Us Agriculture Process for whitening durable-press cellulosic fabrics with basic optical brighteners
US3807946A (en) * 1972-01-24 1974-04-30 Agriculture Process for preparing durable press fabrics which can be dyed with acid dyes
FR2314181A1 (en) * 1975-06-12 1977-01-07 Stamicarbon mixed hydroxymethyl-hydroxyalkylisocyanurates
US4007274A (en) * 1976-03-22 1977-02-08 Imc Chemical Group, Inc. Method of controlling the growth of bacteria and fungi using substituted tetrahydro-s-triazin-2(1H)-one compounds
WO1998010648A1 (en) * 1996-09-13 1998-03-19 The Regents Of The University Of California Durable and regenerable microbiocidal textiles
US6241783B1 (en) 1996-09-13 2001-06-05 The Regents Of The University Of California Formaldehyde scavenging in microbiocidal articles
US20040127667A1 (en) * 2002-06-14 2004-07-01 Worley Shelby D. N-halamine siloxanes for use in biocidal coatings and materials
US6962608B1 (en) 2002-10-01 2005-11-08 The Regents Of The University Of California Regenerable antimicrobial polymers and fibers with oxygen bleaches
US20120085250A1 (en) * 2010-10-12 2012-04-12 Ecolab Usa Inc. Novel method of treating textiles with starch to eliminate sticking

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2326605A (en) * 1941-08-11 1943-08-10 Dow Chemical Co Finishing piece goods
US2400016A (en) * 1945-07-11 1946-05-07 Libbey Owens Ford Glass Co Production of synthetic resin coatings
US2526462A (en) * 1946-11-19 1950-10-17 Pond Lily Company Moisture-resistant flameproofed product and method of making same
US2711971A (en) * 1950-07-14 1955-06-28 Calico Printers Ass Ltd Methylol acetone resin precondensate and method of impregnating fabrics therewith
US2755198A (en) * 1953-02-27 1956-07-17 Monsanto Chemicals Novel compositions and treatment of textile materials
US2769584A (en) * 1954-02-09 1956-11-06 Zinamon Martin Method of permanently pleating fabrics
US2817568A (en) * 1954-06-22 1957-12-24 Joseph Darman Stop mechanism for towel dispensers
US2826500A (en) * 1954-12-30 1958-03-11 Hercules Powder Co Ltd Use of cationic-modified urea-formaldehyde resins in the manufacture of wet strengthpaper

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2326605A (en) * 1941-08-11 1943-08-10 Dow Chemical Co Finishing piece goods
US2400016A (en) * 1945-07-11 1946-05-07 Libbey Owens Ford Glass Co Production of synthetic resin coatings
US2526462A (en) * 1946-11-19 1950-10-17 Pond Lily Company Moisture-resistant flameproofed product and method of making same
US2711971A (en) * 1950-07-14 1955-06-28 Calico Printers Ass Ltd Methylol acetone resin precondensate and method of impregnating fabrics therewith
US2755198A (en) * 1953-02-27 1956-07-17 Monsanto Chemicals Novel compositions and treatment of textile materials
US2769584A (en) * 1954-02-09 1956-11-06 Zinamon Martin Method of permanently pleating fabrics
US2817568A (en) * 1954-06-22 1957-12-24 Joseph Darman Stop mechanism for towel dispensers
US2826500A (en) * 1954-12-30 1958-03-11 Hercules Powder Co Ltd Use of cationic-modified urea-formaldehyde resins in the manufacture of wet strengthpaper

Cited By (46)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3220869A (en) * 1959-03-13 1965-11-30 Basf Ag Process for improving textile fabrics
US3140197A (en) * 1959-04-01 1964-07-07 Heberlein & Co Ag Finished textile and method of producing same
US3043718A (en) * 1959-07-09 1962-07-10 Rohm & Haas Compositions, textiles treated therewith, and processes for the treatment thereof
US3135710A (en) * 1960-09-22 1964-06-02 Rohm & Haas Aqueous dispersion of aminoplast and butene-2-diol-1, 4
DE1283798B (en) * 1960-11-21 1968-11-28 Hooker Chemical Corp A process for Flammfestausruestung of cellulose-containing textile
US3094705A (en) * 1960-12-29 1963-06-25 John D Reid Method for producing a pucker-free seam in a garment
DE1268098B (en) * 1961-02-17 1968-05-16 Calico Printers Ass Ltd A method for anti-wrinkling of cellulose textiles
US3173895A (en) * 1961-04-01 1965-03-16 Hoechst Ag Process for preparing hardenable condensation products from bistriazinones
US3238166A (en) * 1961-10-10 1966-03-01 Sumitomo Chemical Co Brocess for endowing permanent dirtpreventing property and hardness to fabrics of synthetic fibers, and resin composition therefor
US3138802A (en) * 1962-05-25 1964-06-30 Cotton Producers Inst Of The N Process for imparting durable creases, wrinkle resistance and shape retention to cellulosic textile articles
US3301631A (en) * 1962-08-21 1967-01-31 Deering Milliken Res Corp Process of modifying cellulosic textiles with epihalohydrin-triazone reaction products
US3268915A (en) * 1963-04-08 1966-08-30 Koratron Company Inc Process of manufacturing press-free garment with retained creases
US3274189A (en) * 1963-04-22 1966-09-20 Dan River Mills Inc Novel compositions for treating textiles and process for making same utilizing phosphoric acid
US3378397A (en) * 1964-04-09 1968-04-16 Sun Chemical Corp Highly alkylolated textile finishing composition and process for treating textile fabric therewith
US3519562A (en) * 1964-04-28 1970-07-07 Procter & Gamble Textile lubricant
US3197790A (en) * 1964-05-06 1965-08-03 Cotton Producers Inst Of The N Process for imparting durable loft and warmth to cellulosic fabrics
US3434875A (en) * 1964-06-29 1969-03-25 Burlington Industries Inc Textile fabric coated with a high molecular weight methylpolysiloxane elastomer polymer
US3381310A (en) * 1964-08-11 1968-05-07 Stevens & Co Inc J P Permanently creased and pleated fabrics and process for producing same
US3425856A (en) * 1964-09-15 1969-02-04 Riegel Textile Corp Process for producing permanent creases and other desirable properties in textile fabrics
US3445277A (en) * 1964-12-22 1969-05-20 Cotton Producers Inst Differential treatment for improving the shape holding properties of cellulosic fabrics
US3458349A (en) * 1965-01-14 1969-07-29 Sumitomo Chemical Co Process for imparting wet and dry crease resistance to textile fabrics with an n-methylolate acrylamide telomer
US3503145A (en) * 1965-01-14 1970-03-31 Sumitomo Chemical Co Deferred curing process for textile fabrics
US3518043A (en) * 1965-08-17 1970-06-30 Basf Ag Hexahydropyrimidone derivatives and a method of finishing textile material
US3527558A (en) * 1966-01-18 1970-09-08 Burlington Industries Inc Process for treating cellulosic textiles
US3432862A (en) * 1966-03-04 1969-03-18 Harry H Weiler Adjustable size garment
US3512921A (en) * 1966-03-24 1970-05-19 Sun Chemical Corp Treatment of cellulosic textiles with 1 - substituted - 3,5 - dimethylol-2,6-dihydrotriazin-4-one
US3510249A (en) * 1966-04-06 1970-05-05 Dan River Mills Inc Precure process
US3542503A (en) * 1966-06-23 1970-11-24 Us Agriculture Process for imparting wrinkle resistance and recovery properties to cotton stretch fabrics
US3519381A (en) * 1966-08-22 1970-07-07 Chevron Res Method of imparting permanent crease to fabrics containing free hydroxyl groups
US3473948A (en) * 1966-09-29 1969-10-21 Burlington Industries Inc Method of improving resin finished textiles
US3731411A (en) * 1971-06-11 1973-05-08 Burlington Industries Inc Process for producing durable press textiles
US3795480A (en) * 1972-01-24 1974-03-05 Us Agriculture Process for preparing durable-press or wash-wear fabrics which can be whitened with acidic optical brighteners
US3807946A (en) * 1972-01-24 1974-04-30 Agriculture Process for preparing durable press fabrics which can be dyed with acid dyes
US3796540A (en) * 1972-03-28 1974-03-12 Us Agriculture Process for whitening durable-press cellulosic fabrics with basic optical brighteners
US4063020A (en) * 1975-06-12 1977-12-13 Stamicarbon, B.V. Mixed hydroxymethyl-hydroxyalkyl isocyanurates
FR2314181A1 (en) * 1975-06-12 1977-01-07 Stamicarbon mixed hydroxymethyl-hydroxyalkylisocyanurates
US4007274A (en) * 1976-03-22 1977-02-08 Imc Chemical Group, Inc. Method of controlling the growth of bacteria and fungi using substituted tetrahydro-s-triazin-2(1H)-one compounds
WO1998010648A1 (en) * 1996-09-13 1998-03-19 The Regents Of The University Of California Durable and regenerable microbiocidal textiles
US5882357A (en) * 1996-09-13 1999-03-16 The Regents Of The University Of California Durable and regenerable microbiocidal textiles
US6077319A (en) * 1996-09-13 2000-06-20 The Regents Of The University Of California Processes for preparing microbiocidal textiles
US6241783B1 (en) 1996-09-13 2001-06-05 The Regents Of The University Of California Formaldehyde scavenging in microbiocidal articles
US20040127667A1 (en) * 2002-06-14 2004-07-01 Worley Shelby D. N-halamine siloxanes for use in biocidal coatings and materials
US6969769B2 (en) 2002-06-14 2005-11-29 Vanson Halosource, Inc. N-halamine siloxanes for use in biocidal coatings and materials
US20080003438A1 (en) * 2002-06-14 2008-01-03 Auburn University Heterocyclic siloxanes for use in biocidal coatings and materials
US6962608B1 (en) 2002-10-01 2005-11-08 The Regents Of The University Of California Regenerable antimicrobial polymers and fibers with oxygen bleaches
US20120085250A1 (en) * 2010-10-12 2012-04-12 Ecolab Usa Inc. Novel method of treating textiles with starch to eliminate sticking

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