GB484984A - Process for modifying the affinity of fibrous and film-like materials for dyestuffs - Google Patents

Process for modifying the affinity of fibrous and film-like materials for dyestuffs

Info

Publication number
GB484984A
GB484984A GB22106/36A GB2210636A GB484984A GB 484984 A GB484984 A GB 484984A GB 22106/36 A GB22106/36 A GB 22106/36A GB 2210636 A GB2210636 A GB 2210636A GB 484984 A GB484984 A GB 484984A
Authority
GB
United Kingdom
Prior art keywords
incorporating
treating
ethylene imine
mol
vapour
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
GB22106/36A
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
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
Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to GB22106/36A priority Critical patent/GB484984A/en
Priority to US152994A priority patent/US2261294A/en
Priority to NL83344A priority patent/NL50107C/xx
Priority to BE422662D priority patent/BE422662A/xx
Priority to FR826740D priority patent/FR826740A/en
Publication of GB484984A publication Critical patent/GB484984A/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
    • 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
    • D06P1/655—Compounds containing ammonium groups
    • D06P1/66—Compounds containing ammonium groups containing quaternary ammonium groups
    • 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
    • D06M13/385—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 containing epoxy groups
    • 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
    • D06M13/487—Aziridinylphosphines; Aziridinylphosphine-oxides or sulfides; Carbonylaziridinyl or carbonylbisaziridinyl compounds; Sulfonylaziridinyl or sulfonylbisaziridinyl compounds
    • 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
    • D06M15/61—Polyamines polyimines
    • 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
    • D06P1/6426—Heterocyclic 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
    • D06P3/34—Material containing ester groups
    • D06P3/40—Cellulose acetate
    • D06P3/401—Cellulose acetate using acid dyes
    • 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
    • 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

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Coloring (AREA)

Abstract

The affinity for dyestuffs of undyed fibrous and film-like materials containing no basic groups but comprising firmly fixed substances in which acidic salt-forming hydroxyl or acidic mercapto groups, other than thiocarbonic acid groups, are attached to carbon, is modified by treatment with an alkylene imine which reacts with opening of the imine ring or with a salt thereof. The material treated may be organophilic, e.g. acetyl- or ethylcellulose or a vinyl polymerizate or hydrophilie, e.g. cotton or regenerated cellulose. The acid groups may be produced by a preliminary saponification or oxidation (cf. Specification 459,711). Specified types of acid components are polymeric carboxylic acids, anhydrides and esters and interpolymerizates therefrom, ester acids of cellulose, pectin esters, alkyd resins of high acid number, anhydric condensation products from aromatic hydrocarbons with side chains and a : b -unsaturated dicarboxylic acids (cf. Specification 441,016), phenol-aldehyde resins and their acyl derivatives, tannin, acetyltannin, sulphurized phenols and polyvalent mercapto compounds and their acyl derivatives. The acid groups are advantageously saturated with organic bases carrying halogenalkyl groups prior to treatment with the alkylene imines. Specified alkylene imines are ethylene imine and its C-methyl, N-methyl, N-butyl and N-cyclohexyl derivatives and the quaternary iminium salts from N : N1-dimethyl-di(b -chlorethyl) ethylenediamine or N : N1-di(g -chlorob -hydroxypropyl) piperazine. In some cases they may have an aminating action and may be used with other aminating or similarly acting agents, e.g. pyridine, trimethylamine, isoquinoline or triethylphosphine. The fastness of the dyeings and their uniformity when admixtures with animal fibres are to be dyed may be improved by treatment before, during or after the dyeing with an alkylating agent such as dimethyl sulphate, p-toluenesulphonic acid methyl ester, epichlorhydrin, 3-chloro-1 : 2-propylene sulphide, chloracetic acid diethylamide, benzyl chloride, xylylene bromides, 1 : 4-dichlorobutene-2 : 3, chloracetone, 1 : 3-dichloracetone, a : a -dichlorodimethyl ether or diethylethyleneiminium chloride (cf. Specifications 467,173 and 469,457). In examples, acetate artificial silk is adapted to be dyed with acid and in some cases with substantive dyes by (1) incorporating an interpolymerizate from vinyl methyl ether (1 mol.) and maleic anhydride (1 mol.) and treating for 14 hours in a closed vessel at 60 DEG C. with N-butylethyleneimine under rhythmic variation of pressure (cf. Specification 464,823), (2) incorporating the same polymerizate and treating successively with tetra-(g -chloro-b -hydroxypropyl) ammonium chloride for 1 hour at 70 DEG C. and with an atmosphere at 70 DEG C. containing ethylene imine vapour for 4-8 hours, (3) incorporating the same polymerizate and treating with C-methyl-ethylene imine for 8 hours at 75 DEG C., (4) and (25) incorporating a condensation product from phenol (10 mols.) and formaldehyde (7 or 8 mols.) and treating for 7 or 8 hours in a moist atmosphere at 70 DEG C. containing ethylene imine vapour, (5) incorporating an anhydric condensation product from xylene and maleic anhydride and treating for 4 hours with an atmosphere at 60 DEG C. containing ethylene imine vapour, (6) incorporating acetyltannin and treating for 14 hours in an atmosphere at 80 DEG C. containing ethylene imine vapour, (8) incorporating polyvinyl chloracetate and an interpolymerizate as in (1) and treating for 8 hours at 75 DEG C. with an amount of N-methylethylene imine equivalent to the reactive chlorine and the free carboxyl groups, (9) incorporating an interpolymerizate as in (1) and treating with an aqueous solution at 30-35 DEG C. of p ethylene imine, preferably after a preliminary treatment, in presence of sodium acetate, with a reaction product from N-butylamine hydrochloride and epichlorhydrin, (12) incorporating an acetylcellulose esterified with maleic or succinic anhydride partially saponifying by treatment for 8 hours with a moist atmosphere at 70 DEG C. containing ammonia and treating for 8 hours in an atmosphere at 60 DEG C. containing ethylene imine vapour, (19) incorporating an interpolymerizate from vinyl chloride (1 mol.) and maleic anhydride (1 mol.) and treating successively with the reaction product at 50-70 DEG C. from ethylene diamine (1 mol.) and 1 : 2-propylene sulphide (4 mols.) in presence of sodium hydrosulphite and with an aqueous solution of ethylene imine at 40 DEG C., (23) incorporating an interpolymerizate as in (1) and treating for 12 hours in a closed vessel at 90 DEG C. with N-cyclohexylethylene imine, (24) incorporating a product of the action of maleic anhydride on acetyl cellulose of low acetyl content and treatment for 7 hours with a moist atmosphere at 70 DEG C. containing ethylene imine vapour, (26) incorporating an interpolymerizate as in (1) or that from vinyl acetate (1 mol.) and maleic anhydride (1 mol.) and a condensation product from phenol (10 mols.) and formaldehyde (8 mols.) and treating with ethylene imine at 70 DEG C.; acetylcellulose films are adapted to be dyed with acid dyes by incorporating an interpolymerizate as in (1) and (7) treating for 16 hours with an atmosphere at 80 DEG C. containing ethylene imine vapour or (10) suspending overnight at 60 DEG C. above ethylene imine, (18) incorporating acetyl pectin and treating with moist ethylene imine vapour; (11) cellulose nitrate artificial silk is adapted to be dyed with acid dyes by incorporating an interpolymerizate from vinyl ethyl ether (1 mol.) and maleic anhydride (1 mol.), denitrating and treating at 40-80 DEG C. with an aqueous solution of ethylene imine and, preferably after-treating with an alkylating agent e.g. epichlorhydrin (cf. Specification 472,630); (13) viscose artificial silk is adapted to be dyed with acid or substantive dyes by mordanting with tannin and tartar emetic and treating with ethylene imine in aqueous solution or as vapour, preferably after a preliminary treatment with hexa-(g -chloro-b -hydroxypropyl)ethylenedi-ammonium chloride in presence of sodium acetate at 20-70 DEG C., the fastness of the substantive dyeings being improved by a treatment, prior to dyeing, with an alkylating agent or with an isothiourea ether or cyanamide; (14) a cellulose film is adapted to be dyed with acid dyes by incorporating the interpolymerizate from vinyl ethyl ether (1 mol.) and maleic anhydride (1 mol.) and suspending for 2 hours in ethylene imine vapour at 80 DEG C.; (15) a bundle of continuous viscose fibre is treated successively with a sulphurized phenol and with tetra(g -chloro-b -hydroxypropyl)ammonium chloride, in presence of sodium acetate, cut to staple and treated with an aqueous solution at 40 DEG C. of ethylene imine; films of cellulose ethyl ether are adapted to be dyed with acid dyes by (16) incorporating the interpolymerizate from vinyl chloride (1 mol.) and maleic anhydride (1 mol.) and treating successively with water at 60-70 DEG C. and with C-methyl-ethylene imine vapour, (17) incorporating the interpolymerizate from vinyl ethyl ether (1 mol.) and maleic anhydride (1 mol.) and treating with a moist atmosphere containing ethylene imine vapour or (20) incorporating a chlorinated resin from xylene and formaldehyde, which has been reacted with potassium hydrosulphide and acetylated, and heating for 8 hours at 60 DEG C. with ethylene imine and trimethylamine in presence of alcohol vapour; (18) a film of polyvinyl formal is adapted to be dyed with acid dyes by incorporating a novolak from phenol (1 mol.) and formaldehyde (6,5 mols.) and treating with aqueous ethylene imine; cuprammonium artificial silk is adapted to be dyed with acid dyes by swelling with caustic soda, (21) impregnating with a solution of ammonium glycerine-tris-phthalate, or equivalent derivatives of aromatic tricarboxylic or polyoxycarboxylic acids, or pyridine polycarboxylic acids, souring with hydrochloric acid or heating, and suspending for 4 hours in ethylene imine vapour at 60 DEG C., or (22) impregnating with a solution of sodium pentaerthritetetraphthalate, treating with a solution of the reaction product from dodecyltriethylenediamine hydrochloride (1 mol.) and epichlorhydrin (9 mols.) and suspending in ethylene imine vapour; (27) a film of alkali-soluble oxyethylcellulose is adapted to be dyed with acid dyes by incorporating cellulose glycollic acid ether and treating for 4 hours with ethylene imine vapour at 60 DEG C. preferably after a preliminary treatment with a solution of tetra(y-chlor-b -hydroxypropyl) ammonium chloride. Specifications 454,320 455,602, and 455,849, also are referred to.
GB22106/36A 1936-07-24 1936-08-11 Process for modifying the affinity of fibrous and film-like materials for dyestuffs Expired GB484984A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
GB22106/36A GB484984A (en) 1936-07-24 1936-08-11 Process for modifying the affinity of fibrous and film-like materials for dyestuffs
US152994A US2261294A (en) 1936-07-24 1937-07-10 Process of increasing the affinity of fibers and films for acid and substantive dyestuffs
NL83344A NL50107C (en) 1936-07-24 1937-07-13
BE422662D BE422662A (en) 1936-07-24 1937-07-15
FR826740D FR826740A (en) 1936-07-24 1937-07-16 Process for modifying the affinity of natural or artificially formed products, in particular for dyes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2261294X 1936-07-24
GB22106/36A GB484984A (en) 1936-07-24 1936-08-11 Process for modifying the affinity of fibrous and film-like materials for dyestuffs

Publications (1)

Publication Number Publication Date
GB484984A true GB484984A (en) 1938-05-11

Family

ID=32094897

Family Applications (1)

Application Number Title Priority Date Filing Date
GB22106/36A Expired GB484984A (en) 1936-07-24 1936-08-11 Process for modifying the affinity of fibrous and film-like materials for dyestuffs

Country Status (5)

Country Link
US (1) US2261294A (en)
BE (1) BE422662A (en)
FR (1) FR826740A (en)
GB (1) GB484984A (en)
NL (1) NL50107C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106498780A (en) * 2012-09-21 2017-03-15 陶氏环球技术有限责任公司 Dye-fixing agent and method

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2434562A (en) * 1941-10-17 1948-01-13 Textile Foundation Process of treating animal fibers and product thereof
US2545492A (en) * 1948-01-23 1951-03-20 Reid John David Fabrics of a long chain amino-ethoxy cellulose and the method of making the same
NL185638B (en) * 1953-03-26 Texas Instruments Inc METHOD OF CALIBRATION OF AN ELECTRICAL THERMAL SWITCH.
US2784052A (en) * 1954-04-23 1957-03-05 Du Pont Process of preparing waterproof films, fabrics, filaments, and yarns of regenerated cellulose containing within a waterproof addition polymer and products produced therefrom
US2972606A (en) * 1956-05-31 1961-02-21 Wyandotte Chemicals Corp Catalytic aminoethylation of cellulose, cellulose derivatives or polyvinyl alcohol
GB923851A (en) * 1958-04-28 1963-04-18 Director Of Kogyo Gijutsu In A process for improving the properties of synthetic fibres, fabrics, films and moulded articles by the irradiation of ionising rays
BE586572A (en) * 1959-01-15
GB942131A (en) * 1959-04-21 1963-11-20 Montedison Spa Dyeable fibres containing basic organic nitrogen compounds and processes for preparing same
US3290417A (en) * 1965-06-01 1966-12-06 Pittsburgh Plate Glass Co Thermosetting coating compositions modified with an alkylenimine
US3290416A (en) * 1964-06-22 1966-12-06 Pittsburgh Plate Glass Co Methacrylate polymer coating composition modified with an alkylenimine
US3513055A (en) * 1964-11-12 1970-05-19 Fmc Corp Method of preparing heat-sealable composite sheets
US4032293A (en) * 1974-09-09 1977-06-28 The United States Of America As Represented By The Secretary Of Agriculture Preparation of stable strong base cellulosic anion exchangers with red-ox potentials

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106498780A (en) * 2012-09-21 2017-03-15 陶氏环球技术有限责任公司 Dye-fixing agent and method
CN106498780B (en) * 2012-09-21 2019-02-22 陶氏环球技术有限责任公司 A kind of textile fabric

Also Published As

Publication number Publication date
FR826740A (en) 1938-04-07
NL50107C (en) 1941-04-15
BE422662A (en) 1937-08-31
US2261294A (en) 1941-11-04

Similar Documents

Publication Publication Date Title
GB484984A (en) Process for modifying the affinity of fibrous and film-like materials for dyestuffs
US2131120A (en) Manufacture of organic compounds containing basic substituents
US2261295A (en) Artificial textile materials
US2142007A (en) Manufacture of artificial silk
GB695703A (en) Improvements in the treatment of cellulosic textile materials
GB601696A (en) A process for modifying the physical characteristics of cellulosic artificial threads
Franck et al. Some effects of the nature of cross-links on the properties of cotton fabrics
US2267842A (en) Manufacture of artificial materials such as fibers
US2926063A (en) Cellulose anthranilate textile fibers and process for making the same
US2109295A (en) Textile fabric and process of making the same
US2439074A (en) Cellulose acetate fibers having wool dyeing properties and a spinning solution therefor
GB881102A (en) Textile treating composition and process of treating cellulosic textiles therewith
US2116063A (en) Treatment of artificial materials
US2300589A (en) Animalizing cellulosic fibers
US2106298A (en) Treatment of materials
US2498875A (en) Coloring cellulosic materials with diazonium salts and naphthyl ethers
US1986881A (en) New cellulose derivatives and their manufacture
US2051051A (en) New cellulose derivatives and process of making same
GB560375A (en) Production of delustered filaments, films and other products
Fisher New Cotton properties through chemical research
Landells Dimensionally Stable Cellulosic Fabrics
US3414367A (en) Process for making n-substituted aminoethylsulfonylethyl ethers of cellulose
US2536334A (en) Process for making solutions of cellulose and resulting product
US3395971A (en) Production of fibrous cellulose ethers using iodide salts as catalysts
US3854867A (en) Process for reacting sultones with cellulosic materials to produce cellulosic materials having both basic and acidic groups and product produced