US3498736A - Inhibiting cellulose fiber yellowing in alkaline processing at elevated temperatures through utilization of boron salts - Google Patents

Inhibiting cellulose fiber yellowing in alkaline processing at elevated temperatures through utilization of boron salts Download PDF

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US3498736A
US3498736A US96704A US3498736DA US3498736A US 3498736 A US3498736 A US 3498736A US 96704 A US96704 A US 96704A US 3498736D A US3498736D A US 3498736DA US 3498736 A US3498736 A US 3498736A
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alkaline
fiber
boron
medium
reactive
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Harlan B Freyermuth
Raymond L Mayhew
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GAF Corp
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GAF Corp
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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
    • D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
    • D06M11/68—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with phosphorus or compounds thereof, e.g. with chlorophosphonic acid or salts thereof
    • D06M11/70—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with phosphorus or compounds thereof, e.g. with chlorophosphonic acid or salts thereof with oxides of phosphorus; with hypophosphorous, phosphorous or phosphoric acids or their salts
    • D06M11/71—Salts of phosphoric acids
    • 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
    • D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
    • D06M11/01—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with hydrogen, water or heavy water; with hydrides of metals or complexes thereof; with boranes, diboranes, silanes, disilanes, phosphines, diphosphines, stibines, distibines, arsines, or diarsines or complexes thereof
    • 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
    • D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
    • D06M11/80—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with boron or compounds thereof, e.g. borides
    • D06M11/81—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with boron or compounds thereof, e.g. borides with boron; with boron halides; with fluoroborates
    • 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
    • D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
    • D06M11/80—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with boron or compounds thereof, e.g. borides
    • D06M11/82—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with boron or compounds thereof, e.g. borides with boron oxides; with boric, meta- or perboric acids or their salts, e.g. with borax
    • 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
    • D06M13/244—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 sulfur or phosphorus
    • D06M13/248—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 sulfur or phosphorus with compounds containing sulfur
    • D06M13/272—Unsaturated compounds containing sulfur atoms
    • D06M13/278—Vinylsulfonium compounds; Vinylsulfone or vinylsulfoxide compounds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58—Material containing hydroxyl groups
    • D06P3/60—Natural or regenerated cellulose
    • D06P3/66—Natural or regenerated cellulose using reactive dyes
    • 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
    • Y10S8/916—Natural fiber dyeing
    • Y10S8/917—Wool or silk

Definitions

  • This invention relates to a method for the treatment of fibrous material and more particularly to a method for reducing the tendency of fibrous materials to discolor or darken when cured at elevated temperatures in the resence of an alkalizing agent.
  • a number of alkaline heat-curing methods for fibrous materials are known, as for example treatments involving the application of certain crease-proofing or wash-andwear agents, reactive dyestuffs and other functional substances.
  • a chemical reaction takes place between the treating agent (including reactive dyes) and the fiber as a result of which the agent becomes chemically bound to the fiber.
  • an alkalizing agent or alkaline-reacting material is employed as a catalyst, acid-binding agent, or for some other purposes.
  • the color produced by the action of the alkaline material in such heat-curing methods may be destroyed or eliminated by bleaching, as with oxidizing agents such as hydrogen peroxide, sodium hypochlorite and the like.
  • oxidizing agents such as hydrogen peroxide, sodium hypochlorite and the like.
  • Sodium hypochlorite solution performs better than hydrogen peroxide in this bleaching operation but it is less desirable because of undesirable side reactions which may occur.
  • cross-linking agents for crease-proofing, water repellency, etc.
  • optical brighteners or reactive dyestuffs for example, in the dyeing of fibers with reactive dyestuffs, or in the simultaneous treatment of fibers with cross-linking agents (for crease-proofing, water repellency, etc.) and optical brighteners or reactive dyestuffs, the
  • -brightener and/ or dyestuff may be more or less destroyed by the oxidizing bleaching agent. If the amount of color produced during such alkaline heat-curing method is too large, it becomes too difficult to bleach with oxidizing agents such as hydrogen peroxide, the bleaching operation becoming too time-consuming and commercially unfeasible.
  • Another object of this invention is the provision of an alkaline heatcuring method for fibrous materials with a reduced tendency to discoloration.
  • Still another object of this invention is the provision of a process involving treatment of fibrous materials in an alkaline medium followed by drying and heat-curing the treated fibrous materials which process has a reduced tendency to discolor the 3,498,736 Patented Mar. 3, 1970 fibrous materials.
  • the present invention which is based upon the discovery that when the heat-curing step is carried out in the presence of a boron-containing compound, the above described tendency of the fibrous material to discolor is unexpectedly reduced or eliminated. More particularly, the invention broadly comprises the step of heat-curing fibrous material in the presence of an alkalizing agent and a boron-containing compound at a temperature of at least about 250 F. It has been unexpectedly found that even when the use of a boron-containing compound in the alkaline heat-curing of fibrous materials does not completely eliminate color formation, the minimizing effect is great enough to permit commercially practical bleaching of residual color with oxidizing agents such as hydrogen peroxide or oxidizing agents that do not cause undesirable secondary degradations.
  • oxidizing agents such as hydrogen peroxide or oxidizing agents that do not cause undesirable secondary degradations.
  • boric acid and fiuoroboric acid and their metal, ammonium and amine salts, and boron fluoride addition products with such compounds as diethyl ether, Water, lower alcohols such as methanol, ethanol, propanol, and the like, ammonia, aliphatic and aromatic amines such as ethylamine, aniline and the like, carboxylic acids such as acetic, propionic, stearic and benzoic and the like, amides such as acetamide, propionamide and the like, and phenols, thiophenols, cresols, naphthols, and the like.
  • lower alcohols such as methanol, ethanol, propanol, and the like
  • ammonia aliphatic and aromatic amines
  • ethylamine aniline and the like
  • carboxylic acids such as acetic, propionic, stearic and benzoic and the like
  • amides such as acetamide, propionamide and
  • a preferred group of boron-containing compounds operative herein are the ammonium, amine, and metal (including alkaline earth metal and alkali metal) borates such as the metaborates, perborates, and tetraborates.
  • the alkali metal borates such as those of sodium and potassium are preferred because of their economy, availability, solubility properties, etc.
  • operative boroncontaining compounds are the borates of amines such as mono-, diand trimethylamine, -ethylamine-, propylamine, -butylamine, -octylamine, -cyclohexylamine, mono-, di-, and tri-ethanolamine, -propanolamine, -butanolamine, and -octanolamine, aromatic amines such as benzylamine, heterocyclic amines such as morpholine, pyridine and the like, and metals such as calcium, magnesium, zinc, manganese, aluminum, barium, copper, iron, nickel, tin, and the like.
  • amines such as mono-, diand trimethylamine, -ethylamine-, propylamine, -butylamine, -octylamine, -cyclohexylamine, mono-, di-, and tri-ethanolamine, -propanolamine, -butanol
  • boron-containing compounds are the borohydrides of the same cations as referred to in the preceding paragraph with respect to the borates. Those preferred are the alkali metal borohydrides, particularly sodium borohydride.
  • the invention is effected by adding the boron-containing compound to the aqueous alkaline medium containing the functional agent (e.g. brightener or reaciive dyestuff, cross-linking, crease-proofing, wash and wear agent, etc.) in an amount sufficient to obtain the desired reduction in discoloration. This amount will be readily ascertainable in any particular instance by routine experimentation.
  • the functional agent e.g. brightener or reaciive dyestuff, cross-linking, crease-proofing, wash and wear agent, etc.
  • the optimum amount to be employed in any particular instance will depend upon the particular boron-containing compound employed, the functional agent being applied to the fibrous material, the result desired, etc.
  • the borohydrides are extremely effective in relatively small amounts in the lower part of the aforementioned range, and may be employed in proportions of about 0.03 to 0.08% in the aqueous alkaline medium.
  • the borates are generally employed in higher concentrations of about 0.1 to preferably about 0.1 to 1% in the aqueous medium.
  • Said copending application broadly discloses a process comprising treating fibrous materials with an aqueous alkaline medium containing a compound of the formula wherein X is a divalent radical selected from the group consisting of O- and SO R and R are selected from the group consisting of phenylene and lower alkylene groups of 1 to 4 carbon atoms; 71' has a value of 0 to 4; and m has a value of 0 to 1', nbeing 0 when m is 0; and then drying and curing the treated material at a temperature of at least about 250 F.
  • X is a divalent radical selected from the group consisting of O- and SO R and R are selected from the group consisting of phenylene and lower alkylene groups of 1 to 4 carbon atoms
  • 71' has a value of 0 to 4
  • m has a value of 0 to 1', nbeing 0 when m is 0; and then drying and curing the treated material at a temperature of at least about 250
  • the alkylene groups may be methylene, ethylene, and normal and isomeric propylene and butylene.
  • the preferred compound employed in such process is 2,2'-sulfonyl-diethanol but other compounds coming within the scope of said formula generically or specifically disclosed in our said copending application may also be employed.
  • the process in said copending application produces an easy-care or wash and wear reactive finish or fibrous materials. It imparts wet and dry crease resistance in addition to increased resistance to washing, laundry sours, mildew damage, moth damage, shrinkage, chlorine retention, odor and/ or dyeing.
  • the present invention is carried into effect by adding the boron-containing compound to the aqueous alkaline medium, in the form of a solution, emulsion, suspension or other type of dispersion, containing the desired amount of crease-proofing agent.
  • the latter amount is not critical and may range from about 0.5 to 50% or more dependent upon the manner of application of the aqueous medium to the fibrous material, the particular crease-proofing agent employed, the properties desired, and the like.
  • the medium if not already alkaline, is rendered alkaline by addition of any suitable alkaline reacting substance such as sodium or potassium hydroxide, carbonate, bicarbonate, phosphate or the like, or an organic base such as triethanolamine or the like, in an amount suflicient to yield a pH of about 7.5 to 10.5 or more.
  • Sodium carbonate or bicarbonate is preferred for this purpose.
  • the aqueous medium may be applied to the fibrous material .by immersion, padding, spraying, printing or any other desired manner, continuously or otherwise. For overall effects, it is preferred to apply an excess of the aqu ous alkaline medium fo o e by a squeez g step with a liquor pick-up of about 30% or less to or more by weight of the fiber.
  • the aqueous alkaline medium may be appropriately thickened in known manner.
  • the treated material is dried and then cured at a temperature of at least about 250 F.
  • the duration of the curing step will generally vary inversely with the temperature although of course the temperature and duration would depend upon the type of fiber being treated, the identity of the crease-proofing agent, the results desired, etc. In general the curing step will usually range up to 5 minutes or more at 250 F. to as little as 15 seconds or less at 500 F. Too high a curing temperature and/or duration causes fiber damage and is to be avoided. These maximum permissible conditions are readily determinable in any instance.
  • the treated fibrous materia may be simply washed and/0r bleached in known manner with the usual oxidizing agents such as sodium hypochlorite, hydrogen peroxide and the like.
  • oxidizing agents such as sodium hypochlorite, hydrogen peroxide and the like.
  • white materials it is usually desirable to apply a bleaching treatment of the cured fibrous materials directly or, if desired, after an intermediate washing.
  • the present process is of course also applicable for reducing discoloration occurring in the application of any other type of crease-proofing or Wash and wear agent, reactive dyestuff, or any other functional agent involving the use of an aqueous alkaline treating medium followed by an alkaline heat-curing step, or in any such application wherein the alkalinity is first developed during the heat-curing step.
  • Reactive dyestuffs are dyestuffs of any type, inorganic but generally organic, containing a reactive atom or group capable of reacting with the fiber being dyed.
  • the present process is useful in applying all such reactive dyestuffs which are applied from an alkaline medium or from a medium containing a compound which develops alkalinity during the subsequent heat-curing step.
  • dyestuffs which may be nitro dyestuffs, dyestuffs of the azo, anthraquinone, phthalocyanine or any other series, including inorganic, which dyestuffs may be metal free or may contain metal in complex union
  • dyestuffs containing an s-triazinyl radical carrying one or two chlorine or bromine atoms directly attached to the triazine ring dyestuffs containing a pyrimidyl radical carrying one or two chlorine or bromine atoms directly attached to the pyrimidine ring and dyestuffs containing a beta-halogenopropionyl, beta-haloethylsulphonyl, beta-halogenoethylsulphamyl, beta-sulphatoethylsulphonyl, beta-hydroxyethylsulphonyl, chloroacetylamino, beta-(chloromethyl)-beta-
  • Such radicals may if desired be nuclearly substituted either directly to the sulphonyl group or through a methylene or other linkage.
  • Specific examples of such dyestuffs are described in British No. 209,723 in Examples 1 and 2, British No. 298,484 in Example 1, British Nos. 456,343, 460,224, 733,471, 740,533, 775,308, 772,030, 774,925, 780,591, 781,930, 785,120, and 785,222, French Nos. 901,187, and 907,103, Belgium Nos. 497,065, 543,214, 543,215, 543,216 and US. Nos.
  • the present process is employed in reactive dyeing processes in similar manner to its employment in creaseproofing, wash and wear processes.
  • an aqueous nredium containing the reactive dyestufl, boron-containing compound, and alkaline-reacting substance or substance developing alkalinity during the subsequent heatcuring step is applied to the fibrous material to be dyed followed by drying and heat'curing as described above.
  • concentration of dyestuif is of course a matter of choice obvious to skilled dyers, and may range from .05 to 2 or 3% in the treating medium.
  • the invention is also useful in a simultaneous reactive dyeing and creaseproofing process.
  • the process of this invention may similarly be employed in any process for treating fibrous material with resins or any other substance or substances intra-reactive, inter-reactive or reactive with the fiber or otherwise, involving an alkaline heat-curing step.
  • the process of this invention has been found to be highly effective in fiber-improving and reactive dyeing processes applied to cellulose fibers of natural or synthetic type, such as cotton, linen, wood, paper, regenerated cellulose and the like.
  • the fibrous material may be in any of the usual forms and in natural bulk, interwoven or felted form as for example in the form of staple fiber or continuous filaments in bulk form or in the form of tow, rope, yarns, slubbings, warps, fabrics, felts, and the like, and treated as a wound package, running length, fibrous stock, bulk, etc.
  • the process of this invention may be employed for improving other fibers, including natural and synthetic polyamides such as wool, silk, casein, zein, nylon and polyurethane fibers and fibers containing recurring carboxylic or cyano groups or the like in the polymer chain.
  • the process of the present invention finds its greatest advantage in the treatment of white fibrous material, particularly cotton shirting, sheet wear, etc. When employed in a dyeing process, it enables the attainment of brighter and truer shades of dyeings. It will be understood that the present process may be applied to fibrous materials in conjunction with other assistants in addition to the functional agents described above, as for example optical brighteners, stabilizers, softeners, surface active agents, reactive bacteriostats, etc.
  • Example I Cotton print cloth (80 x 80) was padded through an aqueous solution containing 2% sodium carbonate, 12.5% 2,2'-sulfonyldiethanol and 0.2% sodium tetraborate deca-hydrate (Na B O -10H O), commonly known as borax. The pressure on the squeeze rolls had been previously adjusted so that the pickup of the solution was 80% of the weight of the fabric. The fabric was dried and then subjected to heat-curing for three minutes at 300 F. A light cream color was developed which partially washed out upon soaping and the remainder easily bleached with oxidizing agents such as sodium hypochlorite or hydrogen peroxide. The treated fabric possessed excellent crease recovery properties.
  • oxidizing agents such as sodium hypochlorite or hydrogen peroxide.
  • Example I Control example The procedure of Example I was followed except that the sodium tetraborate was omitted.
  • Example II The procedure of Example I was followed except that 1.0% sodium perborate was used in place of 0.2% sodium tetraborate. The effect of the perborate in lessening the color of the cured cloth was roughly equivalent to the tetraborate, and markedly superior to the Control Example.
  • Example III The procedure of Example I was followed except that 0.06% sodium borohydride was used in place of 0.2% sodium tetraborate. The effect of minimizing color was about the same as Example I.
  • Borax 0.3 Blandofen SL (General Aniline & Film Corp., 25%
  • the polythylene emulsion contributes to softness and tear strength.
  • the above bath was applied continuously to cotton broadcloth (136/64 construction) in conventional padding equipment adjusted for pickup of 65- 70%.
  • the padded fabric was dried on a tenter frame and then cured at 360380 F. for 1.5 to 2 minutes.
  • the slight yellowing which occurred during the curing was bleached out in 30-60 seconds at l60l80 F. using a typical bleach solution:
  • the resulting treated fabric had very good wet and dry crease angle recovery (combined warp and filling) in the 250-260 range, with improved appearance rating after spin drying, tumble drying and/'or laundering (home and commercial).
  • said fibertreating agent is a dyestuff reactive with the fiber under dry alkaline conditions at temperatures of at least about 250 F.
  • An aqueous treating medium for cellulosic materials comprising a bis(fi-hydroxyethyhsulfone, an alkaline catalyst and a water-soluble, boron-containing salt.
  • a medium as defined in claim 10 wherein said boron-containing compound is an alkali metal borate.
  • a medium as defined in claim 10 wherein said boron-containing compound is sodium tetraborate.
  • a medium as defined in claim 10 'wherein said boron-containing compound is sodium borohydride.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
  • Paper (AREA)
  • Coloring (AREA)
US96704A 1961-03-20 1961-03-20 Inhibiting cellulose fiber yellowing in alkaline processing at elevated temperatures through utilization of boron salts Expired - Lifetime US3498736A (en)

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US (1) US3498736A (de)
BE (1) BE615098A (de)
CH (1) CH417521A (de)
DE (1) DE1266270B (de)
FR (1) FR1317811A (de)
GB (1) GB995433A (de)
NL (1) NL276022A (de)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4314819A (en) * 1977-09-29 1982-02-09 Sandoz Ltd. Fixation of reactive dyes on cellulosic fibers
FR2663053A1 (fr) * 1990-06-09 1991-12-13 Sandoz Sa Procede de teinture des matieres textiles contenant de la cellulose.
US5240465A (en) * 1990-06-09 1993-08-31 Sandoz Ltd. Process for reactive dyeing a cellulose-containing textile material with anionic dyeing assistant as levelling agent
US10533060B2 (en) * 2015-05-15 2020-01-14 Nippon Paper Industries Co., Ltd. Anion-modified cellulose nanofiber dispersion liquid and composition
CN113322664A (zh) * 2021-05-27 2021-08-31 江南大学 一种特白棉织物的制备方法

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Publication number Priority date Publication date Assignee Title
CN110512302B (zh) * 2019-09-11 2021-11-12 华峰重庆氨纶有限公司 一种表面处理的聚氨酯弹性纤维的制备方法

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US1844718A (en) * 1929-02-23 1932-02-09 Eastman Kodak Co Process for the manufacture of cellulose acetate
FR1227817A (fr) * 1958-07-23 1960-08-24 Rohm & Haas Procédés pour rendre infroissables les tissus cellulosiques et tissus ainsi obtenus
CA625790A (en) * 1961-08-15 Huggett Clayton Crease-proofing cellulosic fabrics, the fabrics obtained and methods of making them
US3042575A (en) * 1958-11-24 1962-07-03 Stiftelsen Svensk Cellulosafor Methods of improving the yield in alkaline digestion of cellulosic material
US3046075A (en) * 1962-07-24 Dyeing and finishing textile materials
US3100732A (en) * 1959-10-05 1963-08-13 Du Pont Process of bleaching wood pulp by combined treatment with peroxide and an alkali metal borohydride
US3178250A (en) * 1961-07-10 1965-04-13 Gen Aniline & Film Corp Fiber improving process and product
US3222119A (en) * 1959-03-10 1965-12-07 Monsanto Co Process for treating cellulosic textile materials with bis(beta-methoxyethyl) sulfone

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GB501206A (en) * 1937-08-23 1939-02-23 Charles Maurice Keyworth Improvements in finishing textile yarns and fabrics
BE523939A (de) * 1952-11-24
DE954502C (de) * 1953-02-19 1956-12-20 Basf Ag Verfahren zum Veredeln von Textilien

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Publication number Priority date Publication date Assignee Title
CA625790A (en) * 1961-08-15 Huggett Clayton Crease-proofing cellulosic fabrics, the fabrics obtained and methods of making them
US3046075A (en) * 1962-07-24 Dyeing and finishing textile materials
US1844718A (en) * 1929-02-23 1932-02-09 Eastman Kodak Co Process for the manufacture of cellulose acetate
FR1227817A (fr) * 1958-07-23 1960-08-24 Rohm & Haas Procédés pour rendre infroissables les tissus cellulosiques et tissus ainsi obtenus
US3218118A (en) * 1958-07-23 1965-11-16 Rohm & Haas Crease-proofing cellulosic fabrics, the fabrics obtained and methods of making them
US3042575A (en) * 1958-11-24 1962-07-03 Stiftelsen Svensk Cellulosafor Methods of improving the yield in alkaline digestion of cellulosic material
US3222119A (en) * 1959-03-10 1965-12-07 Monsanto Co Process for treating cellulosic textile materials with bis(beta-methoxyethyl) sulfone
US3100732A (en) * 1959-10-05 1963-08-13 Du Pont Process of bleaching wood pulp by combined treatment with peroxide and an alkali metal borohydride
US3178250A (en) * 1961-07-10 1965-04-13 Gen Aniline & Film Corp Fiber improving process and product

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4314819A (en) * 1977-09-29 1982-02-09 Sandoz Ltd. Fixation of reactive dyes on cellulosic fibers
FR2663053A1 (fr) * 1990-06-09 1991-12-13 Sandoz Sa Procede de teinture des matieres textiles contenant de la cellulose.
BE1004655A3 (fr) * 1990-06-09 1993-01-05 Sandoz Sa Procede de teinture des matieres textiles contenant de la cellulose.
US5240465A (en) * 1990-06-09 1993-08-31 Sandoz Ltd. Process for reactive dyeing a cellulose-containing textile material with anionic dyeing assistant as levelling agent
CH687355GA3 (de) * 1990-06-09 1996-11-29 Clariant Finance Bvi Ltd Verfahren zum Faerben von Cellulose-Textilmaterial.
US10533060B2 (en) * 2015-05-15 2020-01-14 Nippon Paper Industries Co., Ltd. Anion-modified cellulose nanofiber dispersion liquid and composition
CN113322664A (zh) * 2021-05-27 2021-08-31 江南大学 一种特白棉织物的制备方法
CN113322664B (zh) * 2021-05-27 2022-07-19 江南大学 一种特白棉织物的制备方法

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NL276022A (de)
GB995433A (en) 1965-06-16
CH319762A4 (de) 1966-03-31
BE615098A (de)
DE1266270B (de) 1968-04-18
CH417521A (de) 1967-02-15
FR1317811A (de) 1963-05-08

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