US2512195A - Method of waterproofing cellulose textiles - Google Patents

Method of waterproofing cellulose textiles Download PDF

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Publication number
US2512195A
US2512195A US668004A US66800446A US2512195A US 2512195 A US2512195 A US 2512195A US 668004 A US668004 A US 668004A US 66800446 A US66800446 A US 66800446A US 2512195 A US2512195 A US 2512195A
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Prior art keywords
textiles
proof
aldehyde
reaction
acid
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US668004A
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Bener Christian
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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10Treating 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
    • D06M13/12Aldehydes; Ketones
    • D06M13/127Mono-aldehydes, e.g. formaldehyde; Monoketones
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10Treating 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
    • D06M13/12Aldehydes; Ketones
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/35Heterocyclic compounds
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46Compounds containing quaternary nitrogen atoms
    • D06M13/47Compounds containing quaternary nitrogen atoms derived from heterocyclic compounds
    • D06M13/477Compounds containing quaternary nitrogen atoms derived from heterocyclic compounds having six-membered heterocyclic rings
    • 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
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/17Glyoxal and polyaldehyde treatment of textiles

Definitions

  • the ratio of aldehyde tocarbamide according to the present invention is so chosen that the carbamide is only present in a fraction of the amount required stoichiometrically for the formation of water-proofness and crease-proofness areob-- tained.
  • the excess of aldehyde avoids the formation of resin in thefibre in a quantity which would otherwise impart brittleness to the fibre which objectionable property was imparted by previous methods discussed above.
  • the manner in which the different agents are applied to the textile fibres is immaterial. It may be done either conjointly in a single solution or dispersion or in several component solutions or else by applying the dissolved or dispersed reagents in any desired succession.
  • the work may be effected with or without intermediate drying and, if desired, a heat-aftertreatment may be provided.
  • the latter is, however, required only in particularcases, namely, when certain aldehydes, or substances splitting oil aldehydes, are used, or certain catalysers.
  • ordinary drying that is, hanging the material to dry, sumces for the reaction to be completed.
  • Aldehydes of the aromatic or aliphatic series or derivatives thereof monoor polyaldehydes, aldehydic acids or aldehyde alcoholates, or other derivatives or substitution products of aldehydes, nitrogen containing aldehyde compounds, aldehyde bisulphites, polymerised aldehyde compounds, as well as compounds capable of splitting oif aldehydes.
  • Formaldehyde Formaldehyde
  • acetic aldehyde, paraldehyde, trioxymethylena be used, particularly the latter substances, and more explicitly: organic or inorganic acids'or acid salts thereof capable of splitting off acids, acids of the aliphatic or aromatic series or salts thereof,
  • catalysers the following may be mentioned: boric acid, lactic acid, succinic acid, acetic acid, chloracetic acid, formic acid, oxalic acid, sulphonic acids of the organic series, such as benzene sulphonic acid, sulphanilic acid, 2-amino-8-naphth0l-6-sulphonic acid, l-naphthol-5-sulphonic acid, -amino-B-naphthol-3.6-disulphonic acid and other naphtholoramino-naphthol-sulphonic acids and their salts, ammonium-sulphate, ammonium sulpho-cyanide, salts of phosphoric acids and persulphonic acids, persulphonic acids, salts of the acids derived from sulphur-0r chlorine, aluminium chloride, silicium tetrachloride, acetate of'alumina, anda number of salts of the heavy and light metals
  • a non-shrink finishing treatment is to take place.
  • the catalyser peratures ranging between 60'I5 C.
  • the-measures ordered must be The'same holds'good if sheet-aftertreatment is provided for fixing the'goods'true -'to'the measures ordered.
  • Substances ofithis kind are capable-.of-reacting with the aldehyde 'and of splittingit oii again, so. that, the. expression transmission means is warranted.
  • substances foraserving this purpose the following. enter. into the question: Small amounts of urea, thio-urea,
  • impregnating liquors important additions may be incorporated, such as sizing materials, starch, gelatine, glucose, various sugars, soluble cellulose derivatives, such as methyl-cellulose, etc., further, emulsions of natural or synthetic rubber (latex), natural or synthetic rubber with or without vulcanising agents, colours, pigments, softening agents, fillers, wet ting agents or water repelling or refractory subtances, if desired.
  • sizing materials starch, gelatine, glucose, various sugars, soluble cellulose derivatives, such as methyl-cellulose, etc.
  • emulsions of natural or synthetic rubber (latex), natural or synthetic rubber with or without vulcanising agents, colours, pigments, softening agents, fillers, wet ting agents or water repelling or refractory subtances if desired.
  • the chemicals used for carrying the method into effect may be incorporated with the fabric singly or jointly in dissolved or dispersed state, either by impregnating the fabric throughout or by local application to the fabric in the form of a pattern by printing, spraying, reserve printing, or by partial immersion as well as by mechanical reserving (forming pockets in the fabric by knotting) i with this mode of procedure it is immaterial washingso asto be fast to dimensional change in subsequent washing.
  • This mechanical forming of a pattern may be combined with the application of colours, pigments or metal powder, if desired, incorporated with binders, so that the raised or the depressed portions become light reflecting.
  • the heat aftertreatment is dependent on all the factors hereinbefore mentioned and is carried out in accordance with the finishing effect required to be produced and in consideration of the agents used. Whereas the production of permanent stamping and molding eflects. as well as non shrink finishing brings with it the necessity for applying a separate heat treatment as a precautionary measure, which is also required in carrying out certain modes of the method for tween 140 to 150 C. Further, it is possible to carry out this treatment in autoclaves under pressure and/or under conditions of alternating superand sub-atmospheric pressures in presence or absence of the reaction solution. Moreover, the heating may take place in a gas atmos- CJI phere under pressure or without pressure in which I case the gas or steam'may constitute, substitute or amplify one of the reaction components, or the catalyser.
  • the method according to the invention makes also possible a further improvement of the process.
  • the effect imparted by the Velan was only regarded as a secondary effect to resin formation on the fibre.
  • textile materials made of natural or artificial cellulose as well as mixtures thereof in the form of flocks yarns, mixed yarns, fabrics, mixed fabrics, hosiery, or matted goods are suitable.
  • the textile material canbe treated according to the present method in any condition, such as crude, bleached condition or having been mercerized with acids or alkalies, parchmentized, dyed, printed, embroidered, etc.
  • mixed yarns or mixed fabrics made of the afore-mentioned textiles and of animal fibres or artificial resin fibres or patented goods of all kinds are suitable for being subjected to this refining.
  • Example 1 A cotton fiock in bleached white condition or preliminarily dyed (particularly with genuine dyestuffs) is thoroughly soaked at 35 C. for a longer time with a solution containing 250 g. of 40% formaldehyde solution 100 g. of 10% Velan PF solution 30 g. of dimethylol urea 8 g. of ammonium sulphate 28 g. of sodium acetate diluted with water up to 1000 g.
  • Example 2 A crepe-satin-fabric made of viscose is impregnated in a solution containing and is printed by adding a small amount of a thickener (gum, tragacanth, methyl cellulose), and is subsequently dried at low temperature. Thereupon the fabric, when provided with a required moisture content, inclusive of dry condition, is subjected to a mechanical shaping (stamping, calendering, shoving, etc), and is" then heated to 145 to 155 C. for 6 min. The fabric can then be washed, if desired, whereupon a permanent stamping effect is created. In applying the reaction mixture topically, washing out or slight steaming is required, so that the stamping effect is removed from the area not treated and is thus retained only on the patterned portions.
  • a thickener gaum, tragacanth, methyl cellulose
  • the processing may be such that the fabric after having been impregnated is printed with reserves of a kind preventing reaction with the fibre, whereupon the fabric is subjected either directly to a condensation treatment or prior to this to a. stamping treatment.
  • the reserved portions are tinged darker shades during the subsequent dyeing, whereas in the latter case the reserved portions display no shaping or fashioning after the fabric has been washed out.
  • This modification can be varied by adding dyes or pigments toin the presence of a, catalyst dimethylol urea, an
  • a method for treating cellulose textiles whereby they are rendered shrink-proof, waterrepellent, and crease-proof which comprises applying to said textiles in an aqueous medium and in the presence of an acidcatalyst dimethylol urea, formaldehyde, and octadecyloxymethyl pyridinium chloride, respectively, in the approximate ratios by weight of 3:10-20:1-2 wherein the dimethylol urea is present in a quantity which if used alone would not form a crease-proofing resin coating, and thereafter curing the treated textiles at a temperature which causes a reaction with said textiles and imparts shrink-proof, water-repellent, and crease-proof properties thereto.
  • a method for treating cellulose textiles whereby they are rendered shrink-proof, waterrepellent, and crease-proof which comprises applying to said textiles in an aqueous medium and in the presence of an acid catalyst dimethylol urea, formaldehyde, and octadecyloxymethyl 7 pyridinium chloride, respectively, in the approximate ratios by weight of 0.3:1:0.1 wherein the dlmethylol urea is present in a quantity which if used alone would not form a crease-proofing resin coating, and thereafter curing the treated textiles at a temperature which causes a reaction with said textiles and imparts shrink-proof, water-repellent, and crease-proof properties thereto.

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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)
  • Coloring (AREA)
US668004A 1939-03-04 1946-05-07 Method of waterproofing cellulose textiles Expired - Lifetime US2512195A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH547846X 1939-03-04

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Country Status (5)

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US (1) US2512195A (fr)
BE (1) BE438129A (fr)
FR (1) FR863554A (fr)
GB (1) GB547846A (fr)
IT (1) IT381105A (fr)

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2665261A (en) * 1950-05-12 1954-01-05 Allied Chem & Dye Corp Production of articles of high impact strength
US2671024A (en) * 1950-12-06 1954-03-02 Gen Aniline & Film Corp Stabilization of photographic glyoxal hardening solutions with water soluble boron compounds
US2859136A (en) * 1950-07-08 1958-11-04 Tootal Broadhurst Lee Co Ltd Process for the treatment of fabrics with resinous condensation products
DE1083777B (de) * 1956-12-05 1960-06-23 Phrix Werke Ag Verfahren zur Veredlung von Textilgut aus natuerlicher oder regenerierter Cellulose
US3084071A (en) * 1959-06-11 1963-04-02 American Cyanamid Co Aluminum salts as curing accelerators for aminoplast resins
US3089747A (en) * 1958-04-04 1963-05-14 American Viscose Corp Method of preparing rayon plisse
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
US3139322A (en) * 1958-09-24 1964-06-30 Bancroft & Sons Co J Fabric resination
US3165374A (en) * 1958-09-24 1965-01-12 Bancroft & Sons Co J Process of partially methylenating cellulose textiles
US3190716A (en) * 1962-02-15 1965-06-22 United Merchants & Mfg Process of finishing cellulosic fabrics with aldehyde-containing solutions and said solutions
US3190715A (en) * 1962-02-15 1965-06-22 United Merchants & Mfg Process of imparting wash and wear properties to cellulosic textiles and finishing solutions for use in such process
US3212928A (en) * 1958-09-24 1965-10-19 Bancroft & Sons Co J Catalyst system for fabric finishing process
US3218119A (en) * 1962-02-02 1965-11-16 American Cyanamid Co Method of applying cyclic urea resins to cellulosic textile materials
US3243252A (en) * 1961-05-18 1966-03-29 Bancroft & Sons Co J Process of methylenating cellulose textiles employing a catalyst mixture of acid, acid salt and reducing agent
US3287083A (en) * 1961-06-30 1966-11-22 Bancroft & Sons Co J Formaldehyde modification of cellulose catalyzed by a lewis acid salt and formic acid generated in situ by a peroxide
US3407026A (en) * 1961-02-24 1968-10-22 Deering Milliken Res Corp Soil retention of aminoplast resin-softener-epichlorohydrin modified cellulosic fabrics obviated by inclusion of carboxymethyl cellulose in reaction system
US3451763A (en) * 1963-03-08 1969-06-24 Heberlein Patent Corp Cellulose-containing fabrics and process therefor
US3663974A (en) * 1961-11-28 1972-05-23 Toyo Spinning Co Ltd Treatment of a cross-linking agent-impregnated cellulosic fabric with a gaseous acid catalyst
US3934587A (en) * 1974-06-17 1976-01-27 Roy Gerald Gordon Disposable articles having a water-permeable and water-repellent surface
US4107426A (en) * 1976-07-06 1978-08-15 Roy Gerald Gordon Process for treating cellulose

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL66514C (fr) * 1944-06-05
US2482756A (en) * 1944-06-10 1949-09-27 Bancroft & Sons Co J Flameproofing of fibrous materials
US2482755A (en) * 1945-05-29 1949-09-27 Bancroft & Sons Co J Flameproofing of fibrous material
US2441859A (en) * 1945-06-12 1948-05-18 Alrose Chemical Company Treatment of textile materials with aldehydes
US2550697A (en) * 1946-05-08 1951-05-01 Bancroft & Sons Co J Cloth water bag
US2530175A (en) * 1946-09-27 1950-11-14 Cluett Peabody & Co Inc Stabilization of regenerated cellulose
US2436076A (en) * 1946-09-27 1948-02-17 Cluett Peabody & Co Inc Method of stabilizing against shrinkage textile materials of regenerated cellulose
US2484545A (en) * 1947-01-18 1949-10-11 Alrose Chemical Company Shrinkage control of cellulosic fibers
US2596192A (en) * 1947-05-03 1952-05-13 Dan River Mills Inc Dyeing with pigment coloring matter
US2622960A (en) * 1948-03-16 1952-12-23 A P W Products Company Inc Glyoxal treatment of absorbent paper to improve wet strength
US2680057A (en) * 1948-08-31 1954-06-01 Deering Milliken Res Trust Cyclopropyl quaternary ammonium compounds and process of applying to textiles
GB692258A (en) * 1949-11-22 1953-06-03 Stevensons Dyers Ltd Improvements relating to the anti-shrink and anti-felt treatment of wool
NL77001C (fr) * 1951-07-24
BE534688A (fr) * 1954-01-08
US2810624A (en) * 1954-04-08 1957-10-22 Rohm & Haas Cellulose plisse fabric and method of producing by applying 1, 3-bis(hydroxy-methyl)-2-imidazolidone and chemical shrinking agent
BE593301A (fr) * 1959-07-24
US3197790A (en) * 1964-05-06 1965-08-03 Cotton Producers Inst Of The N Process for imparting durable loft and warmth to cellulosic fabrics

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB312280A (en) * 1928-05-23 1930-07-10 Heberlein & Co Ag Manufacture of acetylated cellulose fibres
GB480171A (en) * 1936-08-15 1938-02-15 Calico Printers Ass Ltd Improvements relating to the treatment of textile fabrics
GB495645A (en) * 1937-05-14 1938-11-14 Ig Farbenindustrie Ag Improving natural or artificial fibrous material
GB495830A (en) * 1937-04-20 1938-11-18 Ig Farbenindustrie Ag Method of treating textile fibrous materials
US2142623A (en) * 1935-11-08 1939-01-03 Calico Printers Ass Ltd Process for the treatment of textile materials
GB500184A (en) * 1937-05-01 1939-02-01 Arthur Ernest Roberts Improvements in and relating to the crease-resisting treatment of textile materials
GB506721A (en) * 1937-08-27 1939-05-30 Tootal Broadhurst Lee Co Ltd Improvements relating to finishing processes for textile materials
GB508173A (en) * 1938-02-01 1939-06-27 Faerberei Ag Process for rendering textiles water-repellent
US2238839A (en) * 1935-08-17 1941-04-15 Watkins William Crease-resisting treatment of textile materials
US2301352A (en) * 1938-03-12 1942-11-10 Heberlein Patent Corp Water-repellent textiles, and process for making same

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB312280A (en) * 1928-05-23 1930-07-10 Heberlein & Co Ag Manufacture of acetylated cellulose fibres
US2238839A (en) * 1935-08-17 1941-04-15 Watkins William Crease-resisting treatment of textile materials
US2142623A (en) * 1935-11-08 1939-01-03 Calico Printers Ass Ltd Process for the treatment of textile materials
GB480171A (en) * 1936-08-15 1938-02-15 Calico Printers Ass Ltd Improvements relating to the treatment of textile fabrics
GB495830A (en) * 1937-04-20 1938-11-18 Ig Farbenindustrie Ag Method of treating textile fibrous materials
GB500184A (en) * 1937-05-01 1939-02-01 Arthur Ernest Roberts Improvements in and relating to the crease-resisting treatment of textile materials
GB495645A (en) * 1937-05-14 1938-11-14 Ig Farbenindustrie Ag Improving natural or artificial fibrous material
GB506721A (en) * 1937-08-27 1939-05-30 Tootal Broadhurst Lee Co Ltd Improvements relating to finishing processes for textile materials
GB508173A (en) * 1938-02-01 1939-06-27 Faerberei Ag Process for rendering textiles water-repellent
US2301352A (en) * 1938-03-12 1942-11-10 Heberlein Patent Corp Water-repellent textiles, and process for making same

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2665261A (en) * 1950-05-12 1954-01-05 Allied Chem & Dye Corp Production of articles of high impact strength
US2859136A (en) * 1950-07-08 1958-11-04 Tootal Broadhurst Lee Co Ltd Process for the treatment of fabrics with resinous condensation products
US2671024A (en) * 1950-12-06 1954-03-02 Gen Aniline & Film Corp Stabilization of photographic glyoxal hardening solutions with water soluble boron compounds
DE1083777B (de) * 1956-12-05 1960-06-23 Phrix Werke Ag Verfahren zur Veredlung von Textilgut aus natuerlicher oder regenerierter Cellulose
US3089747A (en) * 1958-04-04 1963-05-14 American Viscose Corp Method of preparing rayon plisse
US3212928A (en) * 1958-09-24 1965-10-19 Bancroft & Sons Co J Catalyst system for fabric finishing process
US3139322A (en) * 1958-09-24 1964-06-30 Bancroft & Sons Co J Fabric resination
US3165374A (en) * 1958-09-24 1965-01-12 Bancroft & Sons Co J Process of partially methylenating cellulose textiles
US3186954A (en) * 1958-09-24 1965-06-01 Bancroft & Sons Co J Catalyst system for heat curing of fabrics
US3084071A (en) * 1959-06-11 1963-04-02 American Cyanamid Co Aluminum salts as curing accelerators for aminoplast resins
US3407026A (en) * 1961-02-24 1968-10-22 Deering Milliken Res Corp Soil retention of aminoplast resin-softener-epichlorohydrin modified cellulosic fabrics obviated by inclusion of carboxymethyl cellulose in reaction system
US3243252A (en) * 1961-05-18 1966-03-29 Bancroft & Sons Co J Process of methylenating cellulose textiles employing a catalyst mixture of acid, acid salt and reducing agent
US3287083A (en) * 1961-06-30 1966-11-22 Bancroft & Sons Co J Formaldehyde modification of cellulose catalyzed by a lewis acid salt and formic acid generated in situ by a peroxide
US3663974A (en) * 1961-11-28 1972-05-23 Toyo Spinning Co Ltd Treatment of a cross-linking agent-impregnated cellulosic fabric with a gaseous acid catalyst
US3218119A (en) * 1962-02-02 1965-11-16 American Cyanamid Co Method of applying cyclic urea resins to cellulosic textile materials
US3190715A (en) * 1962-02-15 1965-06-22 United Merchants & Mfg Process of imparting wash and wear properties to cellulosic textiles and finishing solutions for use in such process
US3190716A (en) * 1962-02-15 1965-06-22 United Merchants & Mfg Process of finishing cellulosic fabrics with aldehyde-containing solutions and said solutions
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
US3451763A (en) * 1963-03-08 1969-06-24 Heberlein Patent Corp Cellulose-containing fabrics and process therefor
US3934587A (en) * 1974-06-17 1976-01-27 Roy Gerald Gordon Disposable articles having a water-permeable and water-repellent surface
US4107426A (en) * 1976-07-06 1978-08-15 Roy Gerald Gordon Process for treating cellulose

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Publication number Publication date
FR863554A (fr) 1941-04-04
GB547846A (en) 1942-09-15
IT381105A (fr)
BE438129A (fr)

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