Classifications

• • 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
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
  • C08K5/0041—Optical brightening agents, organic pigments
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
  • C09B23/14—Styryl dyes
  • C09B23/145—Styryl dyes the ethylene chain carrying an heterocyclic residue, e.g. heterocycle-CH=CH-C6H5
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B44/00—Azo dyes containing onium groups
  • C09B44/02—Azo dyes containing onium groups containing ammonium groups not directly attached to an azo group
  • C09B44/04—Azo dyes containing onium groups containing ammonium groups not directly attached to an azo group from coupling components containing amino as the only directing group
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B69/00—Dyes not provided for by a single group of this subclass
  • C09B69/001—Dyes containing an onium group attached to the dye skeleton via a bridge
• • 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
  • D01F1/00—General methods for the manufacture of artificial filaments or the like
  • D01F1/02—Addition of substances to the spinning solution or to the melt
  • D01F1/06—Dyes
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03B—APPARATUS OR ARRANGEMENTS FOR TAKING PHOTOGRAPHS OR FOR PROJECTING OR VIEWING THEM; APPARATUS OR ARRANGEMENTS EMPLOYING ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ACCESSORIES THEREFOR
  • G03B1/00—Film strip handling
  • G03B1/18—Moving film strip by means which act on the film between the ends thereof

Definitions

• the present invention relates to the spin-dyeing of acrylonitrile polymers; more particularly it concerns a process wherein polyacrylonitrile or interpolyrners of acrylonitrile and other copolyrnerisable compounds containing at least 70% acrylonitrile are spin-dyed by means of basic dyestuffs which are soluble in the solvents used for the spinning, for instance in dimethyl forrnarnide, dirnethyl sulione, ethylene carbonate or nitro methane.
• basic dyestuffs are used in the spin-dyeing of the acrylonitrile polymers which have been precipitated from their aqueous solutions.
• the basic dyestuffs to be used according to the invention in the spinning process no longer give rise to troubles such as were frequently to be observed in the use of the water soluble basic starting dyestuffs on account of frequently entrained water soluble foreign salts.
• the spinning masses treated with the proposed basic dyestufis yield threads or fibres which possess a fastness to cross-dyeing which is better than that of threads or fibres obtainable from spinning masses which have been treated in the conventional manner with the corresponding water soluble dyestuffs.
• the basic dyestuffs which were precipitated from their aqueous solutions do not tend to clog the spinning nozzles; furthermore they do not bleed when the filaments are stretched in the precipitating bath.
• the basic dyestuffs to be applied according to the invention one can for example proceed by dissolving the basic dyestuffs produced in a customary manner and which can belong to the most various seriese.g. the triphenyl-rnethane series, the anthraquinone series, the azo series, the rnethine series or Le phthalocyanine seriesin water and then adding sulionic acids or water soluble salts of sulfonic acids to the aqueous solutions.
• series e.g. the triphenyl-rnethane series, the anthraquinone series, the azo series, the rnethine series or Le phthalocyanine seriesin water
• sulfonic acids aliphatic acids and aromatic acids come into consideration such as, for example, propane-1,3-disulfonic acid, benzene rnonoor disultonic acid, naphthalene monoor polysulfonic acid, dipheny 4-sulfonic acid and condensation products of formaldehyde with naphthalene sultonic acid or with 4,4-dihydroxy diphenyl sulphone containing sultonic acid groups.
• sulfonic acids or their salts also other acids, such as rnaleic acid, fumaric acid, adipic acid, citric acid, trichloro acetic acid, boroiluoro actic acid, borofluoro butyric acid and hydrofiuoboric acid or their water soluble salts may be used for precipitation.
• water soluble salts the alkali metal salts are especially suitable.
• the precipitation of the basic dyestuffs with the acids or their water soluble salts from the aqueous solutions can be effected in the cold or also with warming, the most suitable temperature being readily determinable in each case by preliminary experiments.
• the suitable proportions of the components can also be etermined by prelirniriary experiments without difliculty; in general it is recommended to-apply the acids or their salts in a slight excess in relation to stoichiometric quantity.
• the basic dyestuffs to be used according to the inven- 5 tion for spin dyeing acrylonitrile polymers include also those basic dyestufis of the azo series which are precipitated by adding the acids or their salts which come into consideration already during the production of the azo dyestuffs, for instance during coupling, instead of after the production of the azo dyestufif.
• the dyestuffs in the present case can, as is customary, be introduced into the spinning masses in the form of stock solutions; stock solutions made up with dimethyl fcrrnarnide can contain for example 15-20% acrylonitrile polymer and -30% dyestuff.
• Example 1 or of the formula 5 were dissolved in 750 ml. of water at 55 C. There was then added with good stirring within 15 minutes 150 g. of a 40% aqueous solution of the sodium salt of the condensation product of formaldehyde with 4,4'-dihydroxy diphenyl sulfone containing sulfonic acid groups. The reaction m xture was further stirred for half an hour and then cooled to 2025 C. T e precipitated red dyestuir" was filtered off with suction, washed with water and dried.
• For the precipitation of the dyestuffs 120 g. of a aqueous solution of sodium propane-1,3,-disulfonate or 40 ml. of borofluoro acetic acid or 40 ml. of hydrofiuoboric acid (13 01.22) can be used instead of 150 g. of the 48% aqueous solution of the condensation product.
• Example 2 The procedure described in Example 1 is followed but instead of the bale dyestuffs used for the spin dyeing, a basic dyestuff is applied which has been precipitated by adding 190 ml. of the 40% solution of the condensation product of Example 1 at 55 C. to an aqueous solution of g. of the yellow dyestuff of the formula is treated, instead of with the 40% aqueous solution of the condensation product of Example 1, with a 40% aque- 3 one solution of the condensation product of formaldehyde and sodium naphthalene sulfonate or sodium naphthalene 1,5-disu1fonate.
• Example 3 The procedure of Example 1 is followed, but instead of the dyestuffs used, the basic dyestufi is applied which precipitates if a solution of 20 g. of the orange coloured dyestufr of the formula is treated at 55 C. with 50 ml. of the 40% aqueous solution of the condensation product applied in Example 1.
• Example 4 The procedure described in Example 1 is followed but instead of the dyestuifs described the basic dyestufi is used which precipitates if at 55 C. the aqueous solution of 20 g. of the blue-black dyestuff of the formula is treated with an aqueous solution of 15 g. of sodium naphthalene-l,5-disulfonate or 15 g. of sodium diphenyl- 4-sulfonate.
• Example 5 The procedure of Example 1 is followed but instead of the dyestuffs described, the basic dyestuff is used which precipitates if a solution of 60 g. of the violet dyestuif of the formula is treated in 700 ml. of water at 80 C. as described in Example 1 with 75 ml. of the 40% aqueous solution of the condensation product indicated in Example 1.
• Example 6 For the sp n dyeing as described in Example 1 a basic dyestutf is used which has been obtained in the following way:
• Example 7 The procedure described in Example 1 is followed using a basic dyestuii: obtained in the following way:
• Example 8 The procedure described in Example 1 is followed but instead of the basic dyestuffs used for the spin dyeing, a basic dyestulf is applied which was precipitated by treating an aqueous solution of 36 g. of the dyestutf of the formula with an aqueous solution of 33 g. of naphthalene-1,5- disulfonic acid sodium salt.
• Example 9 The procedure described in Example 1 is followed but instead of the basic dyestufis used for the spin dyeing, a basic dyestuif is applied which has been precipitated in the following manner:
• the step which comprises using basic dyestuffs which have been precipitated from their aqueous solution by means of a member selected from the group consisting of an aromatic sulfonic acid and a water soluble salt of an aromatic sulfonic acid, said member having at least 2 aromatic rings.
• FOREIGN PATENTS 5 The process of claim 1 wherein the member is 616,440 Great Britaln Jan. 21, 1949 30mm dphenyl'4'sulfnate 10 686,269 Great Britain Ian. 21, 1953 6.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Engineering & Computer Science (AREA)
• Textile Engineering (AREA)
• General Chemical & Material Sciences (AREA)
• General Physics & Mathematics (AREA)
• Manufacturing & Machinery (AREA)
• Physics & Mathematics (AREA)
• Health & Medical Sciences (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
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• 1957
  • 1957-10-18 DE DEF24211A patent/DE1077372B/de active Pending
• 1958
  • 1958-10-13 CH CH6496458A patent/CH376610A/de unknown
  • 1958-10-16 GB GB33097/58A patent/GB855153A/en not_active Expired
  • 1958-10-17 US US767771A patent/US3122517A/en not_active Expired - Lifetime
  • 1958-10-17 FR FR1212939D patent/FR1212939A/fr not_active Expired

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