Classifications

• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
  • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
  • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
  • G03C7/388—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor
  • G03C7/3882—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor characterised by the use of a specific polymer or latex
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
  • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
  • B01J45/00—Ion-exchange in which a complex or a chelate is formed; Use of material as complex or chelate forming ion-exchangers; Treatment of material for improving the complex or chelate forming ion-exchange properties
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F8/00—Chemical modification by after-treatment
  • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
  • C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
• • D—TEXTILES; PAPER
  • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
  • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
  • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
  • D01F6/02—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • D01F6/18—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds from polymers of unsaturated nitriles, e.g. polyacrylonitrile, polyvinylidene cyanide
• • D—TEXTILES; PAPER
  • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
  • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
  • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
  • D01F6/28—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • D01F6/38—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds comprising unsaturated nitriles as the major constituent
• • 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
  • D06M11/58—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 nitrogen or compounds thereof, e.g. with nitrides
  • D06M11/63—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 nitrogen or compounds thereof, e.g. with nitrides with hydroxylamine or hydrazine
• • 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
  • D06M13/376—Oximes
• • 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
  • D06P1/673—Inorganic compounds
  • D06P1/67308—Hydroxylamine or derivatives thereof
• • 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
  • D06P3/70—Material containing nitrile 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
• • 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
  • D21H17/20—Macromolecular organic compounds
  • D21H17/33—Synthetic macromolecular compounds
  • D21H17/34—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • D21H17/41—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing ionic groups
  • D21H17/44—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing ionic groups cationic
  • D21H17/45—Nitrogen-containing groups
  • D21H17/455—Nitrogen-containing groups comprising tertiary amine or being at least partially quaternised
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
  • G03C1/00—Photosensitive materials
  • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
  • G03C1/04—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with macromolecular additives; with layer-forming substances
  • G03C1/053—Polymers obtained by reactions involving only carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
  • G03C1/00—Photosensitive materials
  • G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
  • G03C1/775—Photosensitive materials characterised by the base or auxiliary layers the base being of paper
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
  • G03C1/00—Photosensitive materials
  • G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
  • G03C1/795—Photosensitive materials characterised by the base or auxiliary layers the base being of macromolecular substances
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
  • G03C1/00—Photosensitive materials
  • G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
  • G03C1/825—Photosensitive materials characterised by the base or auxiliary layers characterised by antireflection means or visible-light filtering means, e.g. antihalation
  • G03C1/835—Macromolecular substances therefor, e.g. mordants
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
  • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
  • G03C7/22—Subtractive cinematographic processes; Materials therefor; Preparing or processing such materials
  • G03C7/25—Dye-imbibition processes; Materials therefor; Preparing or processing such materials
• • 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
  • Y10S8/06—Resin bleach
• • 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
  • Y10S8/93—Pretreatment before dyeing
  • Y10S8/931—Washing or bleaching

Definitions

• Uie at This invention relates to the dyeing of fibers, yarns, fabrics and other shaped articles substantially consisting of polymers containing nitrile groups, as defined hereinafter.
• polyacrylonitrile fibers possess outstanding properties, yet the expansion of their technical application is strongly limited by the difiiculties which arise when dyeing these fibers and by the tendency of these fibers to take up static electricity.
• cuprous ion technique which consists in dyeing these fibers in the presence of cuprous ions
• Treatments which superficially change the formed fibers by chemical reaction are for instance: saponification (H. Rein, Angew. Chem. 60 (1948), 159/161), and treatment with organic amines (British Patent No. 700,172) in the presence of sulphonic acid (British Patent No. 712,235) or other mineral substances with acid character.
• Another object is the manufacture of White shaped articles consisting substantially of polymers containing acrylonitrile units with improved dyeability.
• Still another object is the provision of a process for dyeing polyacrylonitrile fibrous material.
• the present invention particularly relates to shaped articles as, for instance, powders, films, fibers, yarns and fabrics, consisting of polymers containing nitrile groups.
• the latter comprise polymers or copolymers, including graft and block copolymers, of acrylonitrile, methacrylonitrile and vinylidene cyanide, and they comprise also cyanoethylated polymers, in the first instance cyanoethylated cellulose, and mixtures of the above polymers with other polymers.
• the process may also be applied successfully to copolymers containing less than 50 percent acrylonitrile units.
• the present invention is especially concerned with the treatment of polyacrylonitrile polymers with an aqueous hydroxylamine solution it must be pointed out that the hydroxylamine treatment may also be carried out in alcoholic medium or even by treating the polymers in solution with hydroxylamine.
• the degree of conversion needed in order to obtain fibers with very good dyeability may vary within wide limits; in some extreme cases a degree of conversion of 10% may be desirable, but in most cases the optimum is about 0.5-5%.
• the degree of conversion is defined as the ratio:
• Weight of polymer converted assuming that the polymer consists exclusively of acrylonitrile and that 1 CN group reacts with l NH OH molecule.
• hydroxylamine is too unstable to be available commercially
• hydroxylamine salts being salts of weak bases, are substantially hydrolyzed and the amount of hyclroxylamine liberated in this way enables the reaction to set in Without liberating the hydroxylamine from its salts by addition of strong bases.
• hydroxylamine treatment may be carried out over practically the 'whole pH range, preferably between 2 and 10.
• polyarnines substances having in their molecule at least two NH groups as well as their derivatives containing at least one amino group capable of being acylated.
• amines may be mentioned: diaminoethane, 1,2-diaminopropane, 1,3-diaminopropane, 1,4-diaminobutane, 1,5 diaminopentane, 1,6 diarnino- 3 hexane, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, aminoethylethanolarriine, diethylaminoeth-ylamine.
• the polyamine may be added to the reaction medium simultaneously with the by droxylamine. If desired, this step may include the addition of the dyestuif. f 7
• reaction temperature for both the hydroxylarnine aiid polyamine treatments may vary Within wide limits. Conveniently both the treatments and dyeing are.ef-
• the chemical treatments may be carried out at' temperatures from 50 C. to 125 0., preferably between 75 and 105 C. Also the dyeing operation may be carried out between these temperature limits, conveniently between 90 C. and the boiling point of theb'ath; if desired, the different operations may be carried out under pressure at higher temperatures.
• fibrous material may be treated in a bath or the material may be part of a close circuit wherein the liquid is pumped through a bed of iibers.
• the treat-merit with hydroxylamine and with polyamine's may also be applied immediately after spinning.
• the discoloration which appears during the treatment of the fibers with polyamines may be removed by a treatment with diluted aqueous solution of strong acids such as sulphuric acid, hydrochloric acid, phosphoric acid, oxalic and malei'c acid.
• This treatment likewise involves an increase of the heat stability.
• the fibers improved according, to the present invention may be dyed with a wide variety of dyes'belonging to difierent classes including acid, direct, disperse, vat, metalliz'able and metal complex dyes, also mixtures of dyes may be used. Although the aflinity for cationic dyes seems notto be increased, yet the fibers remain dyeable with these dyes. Also the Cuprous ion technique. may be used. Likewise noncolored substances, for example clearing and finishing agents, may be fi'ried on the fibrous material.
• the reaction with hydroxylamine and with polyamines will be followed by the dyeing operation, but both may also be carried out in the same bath without changing the main liquid, simply by altering the com-'- position to the end in view.
• the dyeing is carried out in an acid medium which may be obtained by addition of inorganic or of organic acid;
• dyeing assistants, relustering agents and buffering mixtures may be used.
• the present invention can be put into practice in any known dyeing process including printing, although it is the purpose to improve the afiinity for dyes, it is also accompanied by a greater water-absorption which considerably diminishes the receptivity for static electricity.
• EXAMPLE 1 100 g. polyacrylonitrile powder (obtained by emulsion polymerization) are boiled for 2 /2 hours in a solution consisting of 750' ml. water and 5 g. hydroxylaminesulphate (sample A). pH of the solution before the treatment: 3.7, after the treatment: 5.0. i
• samples of the washed powder (A) are boiled for 1 hour in a 1% aqueous solution of ethylenediamine (sample B), hexamethylenediamine (sample C) and diethylaminoetliylamine (sample D).
• sample B ethylenediamine
• sample C hexamethylenediamine
• the samples A, B, C and D are boiled for /2 hour in a dye bath containing 0.2% Fast Red A.V. (CI. 15620) in H 30 N/l0.
• the dye uptake amounts to: 5% for sample A, 16% for sample B, and 14% 'for samples C and D.
• EXAMPLE 3 1100 g. polyacrylonitrile as in Example 1 are treated for 2 hours with 1000 ml. of an aqueous solution containing 10 g. hydroxylaminesulphate and 4 g. NaOH (this quantity of NaOH is sufiicient to liberate 80% of the hydroxylamine)- pH before treatment: 6.7; after the treatment: 8.5.
• the difierent samples are then dyed in the same dye bath consisting of 0.2% Fast Red A.V. (CI. 15620) in H 50, N/lO. V
• the dye uptake amounts to: 10% for A and B, 20% for C, 30% for D and 40% for E.
• EXAMPLE 4 i '10 g. polyacrylonitrile staple fibers (manufactured by Cassella) are boiled for /2 hour in a solution containing 0.5 g. of hydroxylamine hydrochloride, 0.32 g. anhydrous sodium carbonate and 150 ml. water. Thefibers are then thoroughly washed. After removing the excess of water they are boiled for /2 hour with an aqueous diethylaminoethylamine 2% solution. Next, they are rinsed again and pressed out. They possess a yellow color.
• EXAMPLE 5 l V V g. Orlon 42 (a copolymer mainly consisting of acrylonitrile manufactured by Du. Pont de Nemours) staple fibers are boiled up in an aqueous solution of a Wetting agent, rinsed and centrifuged.- Then the fibers are treated wih an aqueous solution consisting of 1250 ml. water, 5 g. hydroxylaminesulphate and 1.6 g. anhydrous sodium carbonate. The quantity of sodium carbonate sufiices to liberate 45% of the hydroxylamine. Next the fibers are boiled for '1 hour in 1 liter 0.5% aqueous'soluticn of diethylaminoethylamine.
• the Slightly yellow"discoloration of the fibers may be removed by treating them for 5 minutes with a 5% oxalic acid solution. -If-insteadof' this last treatment a 5 g. sample of the fibers is boiled for 1 hour in a solution containing 150 ml. water, 0.5 ml. formic acid and 0.25 ml. Calcocid M 9863, black dyeings are obtained.
• EXAMPLE 6 g. polyacrylonitrile staple fibers (manufactured by Cassella) are treated for 1 hour at 90 C. with a solu tion composed of 1 20 cm. of demineralized water, 0.3 g. hydroxylaminesulphate, 0.2 g. of ethylenediamine and 0.14 g. of NaOH. After adding cm. H SO /N and 0.5 g. Neolan Yellow (CI. 19010), the mixture is boiled for /2 hour. The fibers are deeply yellow colored.
• EXAMPLE 8 10 g. Darlan (registered trademark for a copolymer mainly consisting of vinylidene cyanide manufactured by B. F. Goodrich) staple fibers are boiled for 30 minutes in a solution composed of 125 ml. water, 1 g. hydroxylaminesulphate and 0.45 g. NaOH. After adding2 m1. of ethylenediamine solution 70% the mixture is boiled for 30 minutes. Afterwards the pH is brought to 2 by adding sulphuric acid; then 0.25 g. Fast Red AV (C.'I. No. 176) is added and the mixture is further boiled for 30 minutes. Now the bath is practically exhausted.
• Darlan registered trademark for a copolymer mainly consisting of vinylidene cyanide manufactured by B. F. Goodrich
• EXAMPLE 9 This example is an alternative of Example 8 and is characterized thereby that the ethylenediamine and the hydroxylamine are added together from the beginning of the reaction. After this treatment the solution is acidified, whereafter Black Tetracide NBA (Cl. 20740) (an acid dyestufi manufactured by Soc. Carbochimique de Tertre) is added and further boiled for /2 hour.
• Black Tetracide NBA (Cl. 20740) (an acid dyestufi manufactured by Soc. Carbochimique de Tertre) is added and further boiled for /2 hour.
• the fibers are homogeneously black dyed.
• EXAMPLE 10 10 g. Orlon-42 staple fibers (registered trademark of Du Pont de Nemours for staple fibers from a copolymer mainly consisting of acrylonitrile) are boiled for minutes in a solution composed of: 150 ml. water, 0.3 g. hydroxylamine sulphate (3% on the weight of fibers) and 0.14 g. NaOH (sufficient to liberate 95% hydroxylamine).
• Blue Formalan 26 (trade name for metal complex dyestufi manufactured by the Soc. Carbochimique de Tertre) and such a quantity of sulphuric acid whereby the pH of the solution is brought at about 3 are added to the bath.
• EXAMPLE 11 100 g. polyacrylonitrile monofilaments are treated during 15 minutes in a 1% Hostapon T (registered trademark for a wetting agent consisting of oleyl methyl tauride sodium salt manufactured by Farbwerke Hoechst,
• sample A Part of sample A, above, is treated for 3 hours at 90-95 C. in a solution consisting of 1500-ml. water, 5 g. hydroxylaminesulphate' and 2.2 g. NaOH (the quantity of NaOH suffices to neutralize 90% of the hydroxylamine) (sample B).
• Process for improving the dyeability of shaped articles formed from a polymeric substance selected from the group consisting of cyanoethylated cellulose, polyacrylonitrile, polymethacrylonitrile, polyvinylidene cyanide, copolymers mainly consisting essentially of acrylonitrile and copolymers mainly consisting essentially of vinylidene cyanide which comprise the steps of (1) treating said articles for /2 to 2 /2 hours in a solution containing free hydroxylamine in a concentration between 0.12 and 0.4% and (2) after the hydroxylamine treatment to obtain from about 0.5 to 10% conversion of the nitrile groups in said article, further treatment of said article with a 0.16 to 3% aqueous solution of ethylenediamine at 50-125 C. for from /2 to 3 /2 hours.

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• Chemical & Material Sciences (AREA)
• Engineering & Computer Science (AREA)
• Physics & Mathematics (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Textile Engineering (AREA)
• General Physics & Mathematics (AREA)
• General Chemical & Material Sciences (AREA)
• Materials Engineering (AREA)
• Spectroscopy & Molecular Physics (AREA)
• Organic Chemistry (AREA)
• Health & Medical Sciences (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Inorganic Chemistry (AREA)
• Toxicology (AREA)
• Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
• Artificial Filaments (AREA)
• Optical Filters (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Chemical Or Physical Treatment Of Fibers (AREA)
• Coloring (AREA)
• Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

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Citations (3)

• 0
  • BE BE541496D patent/BE541496A/xx unknown
  • BE BE565402D patent/BE565402A/xx unknown
  • BE BE546321D patent/BE546321A/xx unknown
  • NL NL215200D patent/NL215200A/xx unknown
  • BE BE569039D patent/BE569039A/xx unknown
  • NL NL88955D patent/NL88955C/xx active
  • NL NL92192D patent/NL92192C/xx active
  • BE BE565400D patent/BE565400A/xx unknown
  • NL NL200690D patent/NL200690A/xx unknown
  • LU LU33836D patent/LU33836A1/xx unknown
• 1954
  • 1954-09-24 GB GB27702/54A patent/GB786960A/en not_active Expired
• 1955
  • 1955-06-02 GB GB15885/55A patent/GB840797A/en not_active Expired
  • 1955-09-22 FR FR1147427D patent/FR1147427A/fr not_active Expired
  • 1955-09-23 CH CH334656D patent/CH334656A/fr unknown
• 1956
  • 1956-03-26 CH CH344844D patent/CH344844A/fr unknown
  • 1956-05-22 GB GB15859/56A patent/GB838296A/en not_active Expired
  • 1956-06-01 FR FR1153961D patent/FR1153961A/fr not_active Expired
• 1958
  • 1958-03-07 DE DEG24055A patent/DE1149169B/de active Pending
  • 1958-03-10 GB GB7683/58A patent/GB850116A/en not_active Expired
  • 1958-03-10 GB GB7684/58A patent/GB852483A/en not_active Expired
  • 1958-05-09 US US734109A patent/US3083070A/en not_active Expired - Lifetime
• 1959
  • 1959-03-29 DE DEG19309A patent/DE1130593B/de active Pending
  • 1959-06-30 DE DEG27405A patent/DE1148072B/de active Pending
  • 1959-07-01 GB GB22611/59A patent/GB863533A/en not_active Expired

Patent Citations (3)

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