US3653805A - Delayed cure process using formaldehyde vapor to cause creaseproofing - Google Patents

Delayed cure process using formaldehyde vapor to cause creaseproofing Download PDF

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Publication number
US3653805A
US3653805A US762119A US3653805DA US3653805A US 3653805 A US3653805 A US 3653805A US 762119 A US762119 A US 762119A US 3653805D A US3653805D A US 3653805DA US 3653805 A US3653805 A US 3653805A
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Prior art keywords
formaldehyde
fabric
catalyst
process according
cellulosic fiber
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US762119A
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Jose P Gamarra
Ronald Swindler
Katherine W Wilson
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Cotton Inc
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Cotton Inc
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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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/12—Aldehydes; Ketones
    • D06M13/127—Mono-aldehydes, e.g. formaldehyde; Monoketones
    • 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
    • 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
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/04—Polyester fibers
    • 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
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/10—Polyvinyl halide esters or alcohol fiber modification
    • 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
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/21—Nylon

Definitions

  • ABSTRACT Cellulosic materials such as cotton fabrics, preferably preimpregnated with an amide such as urea, are treated with formaldehyde vapor, formed into garments and cured in the presence of a catalyst to impart durable press and wrinkle recovery characteristics to such garments.
  • the required curing catalyst may be furnished either by impregnating the fabrics with an aqueous solution of a weakly acid salt such as zinc chloride after exposure of the fabric to formaldehyde and before garment fabrication therefrom, or by furnishing a gaseous catalyst such as sulfur dioxide to the chamber in which the garments fabricated from the formaldehyde-treated fabric are cured.
  • a more specific object is to provide a process for creaseproofing cotton or other cellulosic materials using formaldehyde vapor as a source from which a reactive but water insoluble creaseproofing agent is evenly formed on the fabric in situ and which permits the cure of the treated material to be safely delayed for long or indefinite periods until after completion of desired articles therefrom including, for instance, the cutting, sewing and pressing of garments.
  • Another specific object is to provide a delayed cure process which produces good wrinkle recovery and smooth drying characteristics, keeps loss of tensile strength and abrasion resistance to a minimum, gives good laundering life and chlorine resistance, employs simple monomeric reactants and, if desired, can produce a pretreated fabric which is relatively insensitive to surrounding conditions and has virtually infinite shelf life prior to final cure.
  • durable press garments or similar articles are made by a novel delayed cure technique from cellulosic fiber-containing material, which process essentially comprises applying formaldehyde vapor to the fabric or material in a first stage, preferably in the absence of any catalyst, under conditions which do not greatly increase the original crease resistance of the material (not enough to interfere with subsequent shaping, pressing, etc., and not enough to provide commercially acceptable creaseproofing), washing water soluble substances from the thus treated material if desired, fabricating articles such as garments from the treated material while it remains easy to crease, pleat or otherwise shape, and only then curing the garments or shaped articles in the presence of an acid or acid-reacting catalyst under conditions which cause the cellulose in the material to become creaseproofed as reflected by its greatly improved crease resistance and wrinkle recovery characteristics.
  • Suitable amide-type formaldehyde binding compounds include various ureas such as urea proper, butyl urea, ethylene urea, cyclic propylene urea, allyl urea, cyclic dihydroxyethylene urea, cyanuramide (melamine), thiourea, as well as formamide acetamide, malonamide, acrylamide, the lower alkyl (e.g., C,-C or hydroxylakyl carbamates such as ethyl carbamate and hydroxyethyl carbamate, aryl sulfonamides such as benzene-sulfonamide or p-benzene-disulfonamide, the lower (e.g., C -C alkyl sulfonamides or bis-sulfonamides such as methane-, ethane-, n-butaneor isobutane-sulfonamide, methylene-bis-methane-s
  • a representative, preferred procedure includes applying the amide compound as an aqueous solution preferably having an alkaline pH of less than about 1 l, e.g., between about 8 and 9, and containing about 1 to 20 percent, e.g., about 10 to 15 percent, of the amide.
  • the resulting fabric is desirably partially dried to a moisture content of between about 7 and 15 percent and in this condition then introduced for about 4 to 20 minutes, e.g., 5 minutes, into fumigation chamber maintained at a temperature of between about and C., and filled with an atmosphere consisting essentially of formaldehyde vapor.
  • Optimum exposure time and temperature depend somewhat on factors such as fabric weight and formaldehyde vapor concentration but are readily determined by routine preliminary tests. Air or any other non-acidic gas which does not react with the formaldehyde or the amide and does not catalyze their reaction with cellulose may be present in the formaldehyde fumigation chamber.
  • a qualitative indication of substantially complete utilization of the N-H groupings in this treatment can be obtained by observing whether the fabric having the amide-formaldehyde condensate formed thereon suffers any noticeable chlorine damage when properly cured and exposed to chlorine bleach.
  • utilization of the N-I-I groupings is substantially incomplete, N-chloro compounds are formed on the fabric by reaction with the bleach and when such a fabric is then washed and ironed visible scorch damage and a noticeable loss in tensile strength take place.
  • a fabric having. an amide-formaldehyde condensate deposited thereon will always be more likely to scorch before the fabric has been properly cured in the presence of an acidic catalyst than after such a cure.
  • the fonnaldehyde After the fonnaldehyde has been affixed on the material as described above, it is preferred to wash the material in hot water with any conventional detergent in order to remove water soluble compounds and to dry it at any convenient manner, e.g., 80 C. in an air oven. In the absence of any acid the treated material is quite insensitive to temperature and not likely to cure prematurely.
  • the fabric may be padded or otherwise impregnated with a latent solid acid catalyst such as a 1-4 percent aqueous solution of zinc chloride, ammonium chloride, sodium dihydrogen phosphate, magnesium chloride, or the like and dried under non-curing conditions.
  • a latent solid acid catalyst such as a 1-4 percent aqueous solution of zinc chloride, ammonium chloride, sodium dihydrogen phosphate, magnesium chloride, or the like and dried under non-curing conditions.
  • a protonic acid such as phosphoric acid is also usable as a catalyst, but only when relatively short storage life is required.
  • the fabric is then ready for use in garment manufacture (e.g., cutting, sewing and pressing) either immediately or after shipment to a different location or after storage of indefinite duration, if desired.
  • the resulting garments may be made shape retentive by baking in an oven at a temperature between about 90 and 175 C., preferably between about 100 and 160 C., for a time of between about 1 and 30 minutes, preferably at a temperature between about 150 and 160 C. for from 2 to minutes.
  • the optimum reaction time under any given set of reaction conditions is one which is just long enough to effect the desired degree of creaseproofing without weakening the fabric by overexposure to the reactants at the elevated temperature.
  • the present invention permits making garments from the cellulosic fabrics after formaldehyde treatment, washing and drying, without previous impregnation with any catalyst, the desired cure of the completed garments being effected in This case by exposing the garments to an acidic vapor such as gaseous sulfur dioxide, hydrogen chloride or formic acid in the baking chamber at a temperature and for a time within the same ranges as described above in connection with the first option.
  • an acidic vapor such as gaseous sulfur dioxide, hydrogen chloride or formic acid
  • Moisture control e.g., addition of steam, may be used to speed up the curing reaction when sulfur dioxide is used as catalyst, this feature being more fully described in copending application Ser. No. 706,792, filed Feb.
  • polymeric additives which are adapted to form soft films on the fabric can also be included in the process of the present invention to give a further improvement in crease retention and other fabric properties.
  • Suitable polymeric additives include solid resinous or rubbery butadiene-acrylonitrile copolymers, polymers of alkyl acrylates, polyethylene, deacetylated copolymers of ethylene and vinyl acetate, polyurethanes and so forth, as is otherwise well known in the art.
  • Such polymers may be applied to the fabric in the form of an aqueous latex or dispersion of finely divided polymer particles either prior to the formaldehyde vapor treatment or afterwards.
  • the aqueous polymer dispersion may be padded onto the fabric either by itself or as part of a bath containing some other agent, e.g., an amide prior to the formaldehyde treatment or a solid salt catalyst after the formaldehyde treatment.
  • the polymers are com monly available in commerce in the form of concentrated aqueous dispersions which can be diluted with additional water and can conveniently be included in padding bath to provide therein a solid polymer content of between about 1 and 5 percent, e.g., 3 to 4 percent.
  • the present invention is useful for treating various natural and artificial cellulosic fibers, as well as various mixtures of such fibers which each other or with other fibers.
  • Natural cellulosic fibers to which this invention is applicable include, for instance, cotton, linen, and hemp.
  • Useful regenerated or artificial cellulosic fibers include viscose rayon and cuprammonium rayon.
  • Other fibers which may be used in blends with one or more of the above mentioned cellulosic fibers are, for example, cellulose acetate, polyamides, polyesters, polyacrylonitrile, polyolefins, polyvinyl chloride, polyvinylidene chloride, polyvinyl alcohol as well as proteinaceous fibers such as wool.
  • the cellulose crosslinking achieved by the present process gives particularly good results when such blends contain at least 20 weight percent, and most preferably at least 40 weight percent, of cotton or other cellulosic fiber.
  • the process of the present invention gives useful results, e.g., dimensional stability, even in the case of fabrics such as wool or wool-polyester blends which do not contain any cellulosic fibers.
  • the fabric may be knit, woven, non-woven or otherwise constructed.
  • the fabric may be flat, creased, pleated, hemmed or formed into any desired configuration prior to the curing step. After curing, the resulting crosslinked fabric will maintain the desired configuration substantially for the life of the article, e.g., a durable press, wash-wear garment can thus be produced.
  • the required formaldehyde vapor may be generated in any convenient manner, such as by heating a suspension of paraformaldehyde in mineral oil to generate formaldehyde gas which is then metered into the treating chamber.
  • any suitable means may be employed to contact the fabric with the gaseous formaldehyde.
  • a batch system utilizing a closed vessel or tube containing a supply of gaseous formaldehyde may be used into which the fabric to be treated may be placed for an appropriate time.
  • a dynamic or continuous system can be used such as one wherein a stream of formaldehyde is passed through a closed elongated chamber through which the fabric is also passed at an appropriate rate, either concurrently or countercurrently relative to the gas stream. It is also possible to use a combination of the above, that is, one may pass a stream of formaldehyde-containing gas over stationary fabric.
  • the reactor used in this work was a cylindrical vessel having a capacity of about 71 liters, constructed of one-eighth-inch aluminum ('42 cm. inside diameter and 57 cm. high).
  • the walls of this reactor are heated with band heaters equipped with a three-way switch which permits operation at 600, 1,200 or 2,400 watts.
  • the reactor wall temperature is controlled by an adjustable bimetallic thermostat, and the reactor is surrounded by an insulating blanket.
  • the gas content of the reactor is recirculated through an external recycle line by an aluminum pressure blower equipped with a heat slinger and hightemperature, lubricated sealed bearings.
  • An adjustable damper in the recycle line permits some control of the pressure within the reactor, but during normal operation nearly atmospheric reactor pressure is preferred.
  • Formaldehyde gas is conducted into the reactor through heated lines from a separate vessel where it is generated as needed by heating a suspension of paraforrnaldehyde in mineral oil.
  • the reactor is further equipped with another line through which other gases such as steam, air and/or sulfur dioxide may be admitted when and as desired.
  • the rate of flow of formaldehyde was controlled by regulating the temperature of the mineral oil between and C.
  • EXAMPLE 1 Formaldehyde Durable Press A 12 X13 inch sample of 80 X80 cotton printcloth was placed on a small frame and immersed into the aluminum reactor described above for one minute while maintaining a formaldehyde flow rate of 3 liters per minute and while maintaining' the reactor wall temperature at 120 C. When removed from the reactor, the fabric was washed in a home laundry machine with one cup of Vel alkylbenzene sulfonate household detergent powder, and dried. This formaldehyde treated fabric had a dry crease recovery of 181 (W & F) as against 179 (W & F) for an untreated control sample. It is evident that at this stage of the process the shape holding characteristics of the fabric were not materially altered.
  • Step 2 each of the samples from Step 1 was padded from a solution of 2 percent zinc chloride and 3 percent Rhoplex K- 87 acrylic resin at 70 percent wet pick-up.
  • the resultant fabrics were dried at 80 C., ironed to set a crease, and cured at 160 C. for 7.5 minutes.
  • Step 1 alone produces a measurable modification of fabric properties, but not enough to interfere with subsequent garment fabrication and far from enough to produce commercially acceptable durable press properties.
  • Step 2 excellent crease recovery is obtained.
  • a minimum add-on of about 0.3 percent is required if formaldehyde alone is used as the creaseproofing agent, or an add-on of at least 1.0 percent is required if a formaldehyde-amide adduct is formed on the fabric, in order to obtain commercially satisfactory performance.
  • fabrics treated in accordance with this invention retain good crease recovery even after acid scouring.
  • EXAMPLE 3 Another series of treatments similar to those described in Example 2 was run, except that in this series each fabric sample was pretreated in Step 1 with a 15 percent solution of a urea compound, with or without a film-forming polymeric additive, and was padded in Step 2 with a solution containing zinc nitrate as a latent catalyst and in some cases also a filmforming polymeric additive, as indicated. All samples were cured 5 minutes at C. Representative data are summarized in Table I. A more complete tabulation of our data from this work may be found in Textile Research Journal, 38, 414, Table IX (1968).
  • the adduct formed between the urea compound and the formaldehyde as a result of the non-catalytic formaldehyde treatment in Step 1 was stable to laundering, and, inasmuch as no strong acid catalyst was used, the fabrics were not weakened by such treatment. After the final cure, marked increases in wrinkle recovery values were observed. Permanent creases or pleats could be effectively pressed into these fabrics at any time after application of the latent catalyst and before the high temperature cure.
  • the treated and cured fabrics show high wash-wear and crease retention ratings along with extended wear life as reflected in the laundering test.
  • the fabrics pretreated with urea were exceptionally white, almost as though an optical brightener had been used.
  • the tear strength of these fabrics was high and flex abrasion resistance good.
  • Their tensile strength retention was in the range between 70 and 75 percent as contrasted to 50-60 percent retention for standard pad-bake resin treatments.
  • Sample cuffs made in accordance with this procedure retained excellent crease recovery after 10 launderings, indicating a stability for the finish which is not characteristic of urea-formaldehyde treatments done by conventional padbake procedures.
  • the fabrics treated in accordance with the present invention may be treated with chlorine bleach without extensive damage, in contrast to fabrics which have been subjected to conventional urea-formaldehyde treatments. Chlorine retention of fabrics treated and cured in accordance with this invention ranges from none to moderate.
  • the amide pad bath used in the pretreatment should have a pH value of not less than 6, preferably between about 7 and 10. At more acid pH values tensile losses of up to 30 percent are found after the initial formaldehyde treatment. Under optimum conditions of urea deposition any tensile loss is usually not more than about 10 percent.
  • Polymeric additives or softeners, as already state, contribute to performance and, as illustrated in Example 3, may be added either with the amide in Step 1 or with the catalyst solution prior to the catalyzed cure.
  • Example 1 was repeated except that the cotton printcloth was pretreated with urea similarly as in Example 2 before the formaldehyde treatment and was not padded with any catalyst in Step 2. Instead, after ironing to set a crease in the formladehyde-treated fabric, it was cured at 1 15 C. for minutes while passing 200 cc. (measured at 24 C.)/min. of S0 and 3 g./min. of steam through the baking oven.
  • step (c) is gaseous sulfur dioxide.
  • step (c) is formic acid.
  • a catalyst which is a solid selected from the group consisting of zinc chloride, ammonium chloride, sodium dihydrogen phosphate, magnesium chloride and phosphoric acid
  • a deferred-cure process wherein the cellulosic fiber-containing fabric is impregnated with an aqueous solution of a water soluble amide at an alkaline pH of less than about 1 1 and dried to produce a dry amide add-on in an amount of between about 0.5 to 25 percent by weight of dry fabric prior to exposure to formaldehyde vapor.
  • a process for the sensitizing of cellulosic fiber-containing fabrics to make them suitable for use in the manufacture of garments which are to be made shape retentive by a hot cure subsequent to their manufacture comprises contacting the fabric with formaldehyde vapor at a temperature between about 105 and 140 C.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US762119A 1968-09-24 1968-09-24 Delayed cure process using formaldehyde vapor to cause creaseproofing Expired - Lifetime US3653805A (en)

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3811131A (en) * 1968-09-24 1974-05-21 Cotton Inc Durable press process for treating cellulosic material with methylolamides and acetic acid or formic acid vapors
US3841832A (en) * 1971-12-06 1974-10-15 Cotton Inc Process for treating cellulosic material with formaldehyde in liquid phase and sulfur dioxide
US3865545A (en) * 1971-09-13 1975-02-11 Mc Graw Edison Co Durable press method
US3884632A (en) * 1973-03-14 1975-05-20 Mc Graw Edison Co Continuous durable-press processing of fabric and garments
US3918903A (en) * 1972-07-25 1975-11-11 Us Agriculture Dehydration process to impart wrinkle resistance to cellulose-containing fibrous materials
US3951595A (en) * 1974-07-10 1976-04-20 Mcgraw-Edison Company Vapor phase process for cellulose fabrics
US4254005A (en) * 1980-02-06 1981-03-03 The United States Of America As Represented By The Secretary Of Agriculture Abrasion resistance and strength of cotton-containing fabric made resilient with N-methylolacrylamide-type reagent
US4255149A (en) * 1979-01-31 1981-03-10 The United States Of America As Represented By The Secretary Of Agriculture Abrasion resistance and strength of cotton-containing fabric made resilient with N-methylolacrylamide-type reagent
USRE30860E (en) * 1971-12-06 1982-02-02 Cotton, Incorporated Process for treating cellulosic material with formaldehyde in liquid phase and sulfur dioxide
US5376144A (en) * 1991-01-23 1994-12-27 American Laundry Machinery, Inc. Process for treating cellulosic fiber-containing fabric
CN109322152A (zh) * 2018-09-28 2019-02-12 江南大学 一种棉织物延迟焙烘免烫整理液及其整理方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB437642A (en) * 1934-02-03 1935-11-04 Calico Printers Ass Ltd Improvements relating to the processing or treatment of fabrics or textile fibres
US2311080A (en) * 1940-11-08 1943-02-16 Du Pont Textile treatment
US2441859A (en) * 1945-06-12 1948-05-18 Alrose Chemical Company Treatment of textile materials with aldehydes
GB980980A (en) * 1961-11-28 1965-01-20 Toyo Spinning Company Ltd Treatment of cellulosic fabrics
US3264054A (en) * 1963-02-08 1966-08-02 Robert M Reinhardt Process for crosslinking cellulosic textile and paper materials with gaseous formaldehyde

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB437642A (en) * 1934-02-03 1935-11-04 Calico Printers Ass Ltd Improvements relating to the processing or treatment of fabrics or textile fibres
US2311080A (en) * 1940-11-08 1943-02-16 Du Pont Textile treatment
US2441859A (en) * 1945-06-12 1948-05-18 Alrose Chemical Company Treatment of textile materials with aldehydes
GB980980A (en) * 1961-11-28 1965-01-20 Toyo Spinning Company Ltd Treatment of cellulosic fabrics
US3264054A (en) * 1963-02-08 1966-08-02 Robert M Reinhardt Process for crosslinking cellulosic textile and paper materials with gaseous formaldehyde

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
Gonzales et al., American Dyestuff Reporter, September 13, 1965, pp. 74 and 105 108 *
Guthrie, Textile Research Journal, Vol. 29, pp. 834 836 (1959) *
Joarder et al., Textile Research Journal, Vol. 37, pp. 1083 1084 (1967) *
Joarder et al., Textile Research Journal, Vol. 39, pp. 49 54 (1969) *

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3811131A (en) * 1968-09-24 1974-05-21 Cotton Inc Durable press process for treating cellulosic material with methylolamides and acetic acid or formic acid vapors
US3865545A (en) * 1971-09-13 1975-02-11 Mc Graw Edison Co Durable press method
USRE30860E (en) * 1971-12-06 1982-02-02 Cotton, Incorporated Process for treating cellulosic material with formaldehyde in liquid phase and sulfur dioxide
US3841832A (en) * 1971-12-06 1974-10-15 Cotton Inc Process for treating cellulosic material with formaldehyde in liquid phase and sulfur dioxide
US3918903A (en) * 1972-07-25 1975-11-11 Us Agriculture Dehydration process to impart wrinkle resistance to cellulose-containing fibrous materials
US3884632A (en) * 1973-03-14 1975-05-20 Mc Graw Edison Co Continuous durable-press processing of fabric and garments
US3951595A (en) * 1974-07-10 1976-04-20 Mcgraw-Edison Company Vapor phase process for cellulose fabrics
US4255149A (en) * 1979-01-31 1981-03-10 The United States Of America As Represented By The Secretary Of Agriculture Abrasion resistance and strength of cotton-containing fabric made resilient with N-methylolacrylamide-type reagent
US4254005A (en) * 1980-02-06 1981-03-03 The United States Of America As Represented By The Secretary Of Agriculture Abrasion resistance and strength of cotton-containing fabric made resilient with N-methylolacrylamide-type reagent
US5376144A (en) * 1991-01-23 1994-12-27 American Laundry Machinery, Inc. Process for treating cellulosic fiber-containing fabric
US5600975A (en) * 1991-01-23 1997-02-11 American Textile Processing, L.L.C. Process and apparatus for treating cellulosic fiber-containing fabric
US5704230A (en) * 1991-01-23 1998-01-06 American Textile Processing, L.L.C. Process and apparatus for treating cellulosic fiber-containing fabric
CN109322152A (zh) * 2018-09-28 2019-02-12 江南大学 一种棉织物延迟焙烘免烫整理液及其整理方法

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DE1947366A1 (de) 1970-04-02
NL6914519A (show.php) 1970-03-26
BE739010A (show.php) 1970-03-02
FR2018750A7 (show.php) 1970-06-26

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