GB716233A - Improvements in the treatment of cellulosic textile materials, films, paper and pulp - Google Patents

Improvements in the treatment of cellulosic textile materials, films, paper and pulp

Info

Publication number
GB716233A
GB716233A GB6140/50A GB614050A GB716233A GB 716233 A GB716233 A GB 716233A GB 6140/50 A GB6140/50 A GB 6140/50A GB 614050 A GB614050 A GB 614050A GB 716233 A GB716233 A GB 716233A
Authority
GB
United Kingdom
Prior art keywords
isocyanate
reaction product
toluene
bisulphite
isothiocyanate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB6140/50A
Inventor
John Gwynant Evans
James Harry Leach
William Salkeld Meals
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bradford Dyers Association Ltd
Original Assignee
Bradford Dyers Association Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to BE501792D priority Critical patent/BE501792A/xx
Priority to BE501793D priority patent/BE501793A/xx
Application filed by Bradford Dyers Association Ltd filed Critical Bradford Dyers Association Ltd
Priority to GB6140/50A priority patent/GB716233A/en
Priority to US213691A priority patent/US2786734A/en
Priority to FR1053828D priority patent/FR1053828A/en
Priority to DEB14105A priority patent/DE939683C/en
Publication of GB716233A publication Critical patent/GB716233A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • D06M13/322—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 nitrogen
    • D06M13/395—Isocyanates
    • 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
    • D06M13/256—Sulfonated compounds esters thereof, e.g. sultones
    • 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
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/62—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds with sulfate, sulfonate, sulfenic or sulfinic groups
    • D06P1/628—Compounds containing nitrogen
    • 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
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/6424—Compounds containing isocyanate or isothiocyanate groups
    • 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
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/22—Effecting variation of dye affinity on textile material by chemical means that react with the fibre
    • D06P5/225—Aminalization of cellulose; introducing aminogroups into cellulose
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06Q—DECORATING TEXTILES
    • D06Q1/00—Decorating textiles
    • D06Q1/08—Decorating textiles by fixation of mechanical effects, e.g. calendering, embossing or Chintz effects, using chemical means
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/03—Non-macromolecular organic compounds
    • D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
    • D21H17/09—Sulfur-containing compounds
    • 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
    • Y10S8/11—Isocyanate and carbonate modification of fibers

Abstract

Fibres, yarns and fabrics composed of or containing natural cellulose, regenerated cellulose or cellulose esters or ethers, or films and foils of regenerated cellulose or cellulose esters or ethers, or paper and pulp are given modified dyeing properties, a reduced water inhibition, a reduced swelling in water, an increased wet strength and an increased resistance to shrinkage by applying thereto a reaction product of an organic mono- or poly-functional isocyanate or isothiocyanate and an alkali metal bisulphite and then heating to a temperature at least as high as the decomposition temperature of the reaction product, e.g. to 100-200 DEG C. The reaction product may be applied in aqueous solution or dispersion or, alternatively, the reaction product may be formed in situ on the material by either applying, in any order, an aqueous solution of the bisulphite and an organic solvent solution of the isocyanate or isothiocyanate, or by applying an emulsion of the isocyanate in an aqueous bisulphite solution. The impregnated material may be partially dried prior to the heating step, or alternatively, the drying and heating operations may be effected simultaneously. Heating may be effected with hot air, infra-red radiation, molten metal or steam. Local or pattern effects may be obtained by printing the reaction product on the material, or alternatively, by the pre-application of resists or the subsequent application of a discharge paste prior to the heat treatment. The treated materials have a high or improved affinity for acid, chrome, basic, direct and dispersed insoluble dyes which may be applied to the materials simultaneously with the reaction product. When dyes sensitive to reduction by the reaction product are applied, anti-reducing agents, e.g. sodium-m-nitro-benzene sulphonate, are incorporated. The wet strength of paper and films of regenerated cellulose and cellulose esters and ethers is considerably increased if an amide, e.g. urea, thiourea, acetamide, benzene sulphonamide, p-toluene sulphonamide or dicyandiamide, is present on the material during the heat treatment. Softening and lubricating agents, antiseptics and anti-crease agents, e.g. thermo-setting resinous condensates, may be applied to fabrics before, after or simultaneously with the reaction product. Reaction products of bisulphites with both aliphatic and aromatic isocyanates and isothiocyanates, e.g. phenyl isocyanate, hexamethylene di-isocyanate, m-toluylene di-isocyanate, m-phenylene di-isocyanate and the corresponding isothiocyanates, allyl isothiocyanate, toluene-2:4-di-isocyanate, toluene - 2:4:6 - tri-isocyanate, mixtures of toluene 2:4-and:2:6-di-isocyanates, methylene bis-p-phenylene isocyanate and the mixture of poly-isocyanates known under the Registered Trade Mark "Vulcafor V.C.C.," may be employed. Numerous examples are given of the treatment of cotton and viscose rayon fabrics and paper, and in some cases the fabrics are simultaneously or subsequently dyed. Specifications 317,019, [Class 15 (ii)], and 716,232 are referred to.ALSO:Bisulphite-organic isocyanate and bisulphite-organic isothiocyanate reaction products, suitable for use in the treatment of textiles, films and paper (see Groups IV (a), IV (c) and VIII), are prepared by dispersing the liquid isocyanate or isothiocyanate or a solution of the solid isocyanate or isothiocyanate in an organic solvent such as benzene, toluene or xylene, into a saturated aqueous solution of the bisulphite, e.g. sodium or potassium bisulphite, from which the reaction product separates out. Reaction products of sodium or potassium bisulphites with phenyl isocyanate, hexamethylene di-isocyanate, m-toluylene di-isocyanate, m-phenylene di-isocyanate and the corresponding isothiocyanates, allyl isothiocyanate, toluene 2 : 4-di-isocyanate, toluene 2 : 4 : 6-tri-isocyanate, mixtures of toluene 2 : 4- and 2 : 6-di-isocyanates, methylene bis-p-phenylene isocyanate and the mixture of polyisocyanates known under the Registered Trade Mark "Vulcafor" V.C.C. are specified. In example XIV, after first preparing the sodium bisulphite reaction product of hexamethylene diisocyanate, it is dissolved in water, the solution heated to 60 DEG C., with the addition of potassium chloride and on cooling to 5 DEG C. the more sparingly soluble potassium bisulphite reaction product crystallizes out.ALSO:Fibres, yarns and fabrics composed of or containing natural cellulose, regenerated cellulose or cellulose esters or ethers, or films and foils of regenerated cellulose or cellulose esters or ethers, or paper and pulp are given modified dyeing properties, a reduced water imbibition, a reduced swelling in water, an increased wet strength and an increased resistance to shrinkage by applying thereto a reaction product of an organic mono- or polyfunctional isocyanate or isothiocyanate and an alkali metal bisulphite, and then heating to a temperature at least as high as the decomposition temperature of the reaction product, e.g., to 100 DEG -200 DEG C. The reaction product may be applied in aqueous solution or dispersion or, alternatively, the reaction product may be formed in situ on the material by either applying, in any order, an aqueous solution of the bisulphite and an organic solvent solution of the isocyanate or isothiocyanate, or by applying an emulsion of the isocyanate in an aqueous bisulphite solution. The impregnated material may be partially dried prior to the heating step, or alternatively, the drying and heating operations may be effected simultaneously. Heating may be effected with hot air, infra-red radiation, molten metal or steam. Local or pattern effects may be obtained by printing the reaction product on the material, or alternatively, by the pre-application of resists or the subsequent application of a discharge paste prior to the heat treatment. The treated materials have a high or imposed affinity for acid, chrome, basic, direct and dispersed insoluble dyes which may be applied to the materials simultaneously with the reaction product, this latter mixture constituting a marketable composition. When dyes sensitive to reduction by the reaction product are applied, anti-reducing agents, e.g., sodium-m-nitrobenzene sulphonate, are incorporated. The wet strength of paper and films of regenerated cellulose and cellulose esters and ethers is considerably increased if an amide, e.g., urea, thiourea, acetamide, benzene sulphonamide, p-toluene sulphonamide or dicyandiamide, is present on the material during the heat treatment. Softening and lubricating agents, antiseptics and anti-crease agents, e.g., thermosetting resinous condensates, may be applied to fabrics before, after or simultaneously with the reaction product. Reaction products of bisulphites with both aliphatic and aromatic isocyanates and isothiocyanates, e.g., phenyl isocyanate, hexamethylene di-isocyanate, m-toluylene di-isocyanate, m-phenylene di-isocyanate and the corresponding isothiocyanates, allyl isothiocyanate, toluene 2:4 di-isocyanate, toluene 2:4:6 tri-isocyanate, mixtures of toluene 2:4 and 2:6 di-isocyanates, methylene bis-p-phenylene isocyanate and the mixture of polyisocyanates known under the Registered Trade Mark "Vulcafor" V.C.C. may be employed. Numerous Examples are given of the treatment of cotton and viscose rayon fabrics and paper, and in some cases the fabrics are simultaneously or subsequently dyed. Specifications 317,019. [Class 15(ii)], and 716,232 are referred to.
GB6140/50A 1950-03-10 1950-03-10 Improvements in the treatment of cellulosic textile materials, films, paper and pulp Expired GB716233A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
BE501792D BE501792A (en) 1950-03-10
BE501793D BE501793A (en) 1950-03-10
GB6140/50A GB716233A (en) 1950-03-10 1950-03-10 Improvements in the treatment of cellulosic textile materials, films, paper and pulp
US213691A US2786734A (en) 1950-03-10 1951-03-02 Process of fixing mechanical finishes to cellulose fabrics by applying isocyanate-bisulphite addition salts
FR1053828D FR1053828A (en) 1950-03-10 1951-03-09 Process for the treatment of cellulosic materials with a view to dyeing and finishing
DEB14105A DE939683C (en) 1950-03-10 1951-03-10 Process for the production of durable, mechanically produced finishing effects on cellulose material or silk

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB6140/50A GB716233A (en) 1950-03-10 1950-03-10 Improvements in the treatment of cellulosic textile materials, films, paper and pulp

Publications (1)

Publication Number Publication Date
GB716233A true GB716233A (en) 1954-09-29

Family

ID=9809151

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6140/50A Expired GB716233A (en) 1950-03-10 1950-03-10 Improvements in the treatment of cellulosic textile materials, films, paper and pulp

Country Status (5)

Country Link
US (1) US2786734A (en)
BE (2) BE501793A (en)
DE (1) DE939683C (en)
FR (1) FR1053828A (en)
GB (1) GB716233A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3492081A (en) * 1965-06-08 1970-01-27 Container Corp Method of treating paper with isocyanates blocked with cyclohexanol
GB2195665A (en) * 1986-08-19 1988-04-13 Nat Res Dev Dyeable cellulosic fibrous materials

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2866722A (en) * 1955-05-20 1958-12-30 Bayer Ag Process for the production of foamed urethan coatings
GB890753A (en) * 1959-04-20 1962-03-07 Ici Ltd Process for modifying cellulosic textile materials
AU499789B2 (en) * 1973-04-16 1979-05-03 Commonwealth Scientific And Industrial Research Organisation (poly)carbamoyl sulphonate containing composition
US20060240730A1 (en) * 2005-04-26 2006-10-26 Demott Roy P Wash durable anti-static treatment for textiles and textiles so treated
JP4550906B2 (en) * 2008-01-07 2010-09-22 株式会社モンベル Fabric products

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2121005A (en) * 1933-10-14 1938-06-21 Firm Raduner & Co A G Process of producing textiles with calender finish permanent to washing and product thereof
DE767329C (en) * 1933-11-25 1952-05-26 Raduner & Co Ag Process for finishing textile fabrics made from cellulose fibers
US2123153A (en) * 1935-04-04 1938-07-05 Celanese Corp Printing and other textile treatments
US2370405A (en) * 1935-05-02 1945-02-27 Heberlein Patent Corp Process for rendering material water-repellent and products therefrom
DE688119C (en) * 1935-05-03 1940-02-13 Faerberei Ges Flores & Co Vorm Process for refining cellulose and cellulose derivative fiber material
US2217696A (en) * 1937-01-21 1940-10-15 Ici Ltd Resist color printing
US2284895A (en) * 1937-10-08 1942-06-02 Du Pont Treatment of textiles to impart water-repellence
US2303364A (en) * 1937-11-08 1942-12-01 Heberlein Patent Corp Process and product for making textile and other material water repellent
US2339913A (en) * 1942-02-27 1944-01-25 Du Pont Cellulose treatment process
US2468716A (en) * 1947-04-16 1949-04-26 American Cyanamid Co Treatment of hydrogen-donor textile materials and products thereof
US2643958A (en) * 1949-08-03 1953-06-30 Bayer Ag Textile printing paste and method of coating therewith
BE501972A (en) * 1950-03-21 1900-01-01

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3492081A (en) * 1965-06-08 1970-01-27 Container Corp Method of treating paper with isocyanates blocked with cyclohexanol
GB2195665A (en) * 1986-08-19 1988-04-13 Nat Res Dev Dyeable cellulosic fibrous materials

Also Published As

Publication number Publication date
BE501793A (en)
US2786734A (en) 1957-03-26
BE501792A (en)
FR1053828A (en) 1954-02-05
DE939683C (en) 1956-03-01

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