US3281260A - Process for treating acrylonitrile fibers with ultra-violet light stabilizer - Google Patents

Process for treating acrylonitrile fibers with ultra-violet light stabilizer Download PDF

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Publication number
US3281260A
US3281260A US238736A US23873662A US3281260A US 3281260 A US3281260 A US 3281260A US 238736 A US238736 A US 238736A US 23873662 A US23873662 A US 23873662A US 3281260 A US3281260 A US 3281260A
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United States
Prior art keywords
percent
fibers
ultra
violet light
acrylonitrile
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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 - Lifetime
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US238736A
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English (en)
Inventor
Pompelio A Ucci
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Monsanto Co
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Monsanto Co
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 NL300694D priority Critical patent/NL300694A/xx
Priority to NL300695D priority patent/NL300695A/xx
Application filed by Monsanto Co filed Critical Monsanto Co
Priority to US238736A priority patent/US3281260A/en
Priority to GB44415/63A priority patent/GB1028867A/en
Priority to GB44681/63A priority patent/GB1033948A/en
Priority to LU44821D priority patent/LU44821A1/xx
Priority to LU44820D priority patent/LU44820A1/xx
Priority to DE19631494666 priority patent/DE1494666A1/de
Priority to FR954073A priority patent/FR1374840A/fr
Priority to SE12710/63A priority patent/SE316564B/xx
Priority to DE19631494667 priority patent/DE1494667A1/de
Priority to CH1410963A priority patent/CH437623A/fr
Priority to CH1411063A priority patent/CH437624A/fr
Priority to DK540763AA priority patent/DK111038B/da
Priority to SE12711/63A priority patent/SE317155B/xx
Priority to DK540863AA priority patent/DK111426B/da
Priority to JP38061901A priority patent/JPS4815209B1/ja
Priority to BE640143A priority patent/BE640143A/xx
Priority to BE640144A priority patent/BE640144A/xx
Priority to FR954201A priority patent/FR1374864A/fr
Application granted granted Critical
Publication of US3281260A publication Critical patent/US3281260A/en
Priority to US647241A priority patent/US3402014A/en
Priority to US647242A priority patent/US3380798A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • 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
    • D06P3/76—Material containing nitrile groups using basic dyes
    • 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
    • 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
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/41—Compounds containing sulfur bound to oxygen
    • C08K5/42—Sulfonic acids; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/18—Homopolymers or copolymers of nitriles
    • C08L33/20—Homopolymers or copolymers of acrylonitrile
    • 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
    • D01F11/00—Chemical after-treatment of artificial filaments or the like during manufacture
    • D01F11/04—Chemical after-treatment of artificial filaments or the like during manufacture of synthetic polymers
    • D01F11/06—Chemical after-treatment of artificial filaments or the like during manufacture of synthetic polymers of macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • D01F6/16—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 carboxylic acids or unsaturated organic esters, e.g. polyacrylic esters, polyvinyl acetate
    • 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
    • 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
    • D01F6/44—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds as major constituent with other polymers or low-molecular-weight compounds
    • D01F6/54—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds as major constituent with other polymers or low-molecular-weight compounds of polymers of unsaturated nitriles
    • 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
    • D06P1/52—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 synthetic macromolecular substances
    • D06P1/5207—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • D06P1/525—Polymers of unsaturated carboxylic acids or functional derivatives thereof
    • D06P1/5257—(Meth)acrylic acid
    • 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
    • D06P1/621—Compounds without nitrogen
    • D06P1/622—Sulfonic acids or their salts

Definitions

  • This invention relates to a method for improving the heat and light stability during the spinning, subsequent processing and use of a synthetic linear fiber. More specifically, this invention is concerned with a method of producing acrylic fibers which are stable to heat and light degradation not only during the spinning process but also through subsequent normal usage such as dyeing, texturizing and bleaching.
  • An object of this invention is to provide a method for tabilizing synthetic linear fibers against degradation due to normal sunlight.
  • Another object of this invention is to provide a method for improving the color and light stability of acrylic yarns or fibers.
  • Another object of this invention is to provide a method for improving the color and light stability of fibers or yarns composed of at least 80 percent acrylonitrile and up to 20 percent of another mono-olefinic copolymerizable monomer.
  • Another object of this invention is to provide a method for the improvement in color and light stability of fibers composed of 94 percent acrylonitrile and 6 percent vinyl acetate.
  • Another object of this invention is to provide a method for improving the color and light stability of fibers composed of a blend of two copolymers, 88 percent of the first copolymer being 94 percent acrylonitrile and 6 percent vinyl acetate, and 12 percent of the second copolymer being 50 percent acrylonitrile and 50 percent methylvinypyridine.
  • Another object of this invention is to provide a method for the improvement in color and light stability of bleached acrylic fibers against ultra-violet light degradation.
  • the objects of this invention are accomplished by treating the fiber during its spinning operation and while it is still in the gel state with a metallic salt of 3,281,260 Patented Oct. 25, 1966 the naphthalene disulfonic acids or the naphthalene disulfonic acids alone.
  • the objects of this invention are obtained by treating the acrylic fibers as they are spun through a conventional spinning operation and are still in the gel state with an additive which is one of the naphthalene disulfonic acids or the alkali metal salts of the naphthalene disulfonic acids.
  • salts are for example; the sodium salt of 1,5, naphthalene disulfonic acid, the potassium salt of 1,5, naphthalene disulfonic acid, or any of the alkali metal salts of any of the naphthalene disulfonic acids such as in addition to 1,5, naphthalene disulfonic acid, 1,3, naphthalene disulfom'c acid, 1,2, naphthalene disulfonic acid, 1,6, naphthalene disulfonic 1,7, naphtha-lene disulfonic acid etc.
  • the amount of this metallic salt or the acid itself which may be used or added to fibers may vary from .001 percent to 5 percent based upon the weight of the fiber with the preferred amount being 0.1 percent based upon the weight of the fiber.
  • the conventional methods of spinning of acrylic fibers are well known in the art and are not germane to this present invention except that these stabilizing additives are applied to the fibers during this conventional spinning process while the fiber is still in the gel state.
  • the polymeric materials which may be employed in the practice of the present invention, are polyacrylonitrile, copolymers, including binary and ternary polymers containing at least percent by weight of acrylonitrile in the polymer molecule, or a blend comprising polya-crylonitrile or copolymers comprising acrylonitrile with from 2 percent to 50 percent of another polymeric material, the blend having an overall polymerized acrylonitrile content of at least 80 percent by weight.
  • the preferred polymers employed in the instant invention are those con-v taining at least 80 percent of'acrylonitrile, generally recognized as the fiber forming acrylonitrile polymers, it will be understood that the invention is likewise applicable to polymers containing less than 80 percent acrylonitrile.
  • the acrylonitrile polymers containing less than 80 percent aorylonitrile are useful in forming film, coating compositions, molding operations, lacquers and also in forming the modacrylic fibers.
  • Suitable mono-olefinc monomers include acrylic, aipha-chloroacrylic and methacrylic acid; the acrylates, such as methylrnJe-thacrylate, ethylmethacrylate, butylmethacrylate, methoxymethyl methacrylate, beta-chloroethyl mlethacrylate and the corresponding esters of acrylic and alpha-chloroacrylic acids; vinyl chloride, vinyl fiuorride, vinyl bromide, vinylidene chloride, l-chloro-l-bromoethylene; methacrylonitrile; acrylamide and methacrylamide; alpha-chloro-acrylamide; or monoalkyl substituted products thereof; methylvinylketone; vinylcarbox
  • the polymeric material when it comprises a blend, it will be a blend of a copolymer of 90 percent to 98 percent acrylonitrile and from 2 percent to 10 percent of another mono-olefinic monomer, such as vinyl acetate, with sufficient amount of copolymer of from 10 percent to 70 percent of acrylonitrile and from 30 percent to 90 percent of a vinyl-substituted tertiary heterocycli'c amine, such as vinylpyridine or l-vinylirnidazole, to give a dyeable blend having an overall vinyl-substituted tertiary heterocyclic amine content of from 2 percent to 10 percent, based on the weight of the blend.
  • a copolymer of 90 percent to 98 percent acrylonitrile and from 2 percent to 10 percent of another mono-olefinic monomer, such as vinyl acetate with sufficient amount of copolymer of from 10 percent to 70 percent of acrylonitrile and from 30 percent to 90 percent of a vinyl-
  • Example 1 A dope composed of 94 percent acrylonitrile and 6 percent vinyl acetate and a conventional solvent was extruded into a conventional coagulating bath composed of water and solvent in filamentary form, stretched, washed and before drying then passed through a conventional finish bath composed of the usual lubricating agents, anti-static agents, softening agents; anti-soiling agents, etc., and 0.1 percent, based upon the weight of the fiber, of 1,5, naphthalene disulfonic acid. The fibers were then dried and passed through the conventional textile machinery. The fibers were then subjected to testing by a recording spectrophotometer, made by General Electric Company.
  • the fibers prior to being tested by the spectrophotometer was subjected to bleaching with a chlorite.
  • the fibers after bleaching were then divided into two parts, the first part being exposed to ultra-violet light and the second part remaining unexposed.
  • After being checked with the spectrophotometer concerning lightness it was found that the fibers exposed to ultra-violet light had a lightness of 82.6 and the part of the fibers which were not exposed .to ultraviolet light had a lightness of 89.7.
  • the fibers exposed to ultra-violet light had a purity of 7.8 and the fibers which were not exposed to ultra-violet light had a purity of 1.6.
  • Example 2 A dope composed of 94 percent acrylonitrile and 6 percent vinyl acetate and a conventional solvent was extruded into a conventional coagulating bath as in Example 1 and the stabilizing additive 1,5, naphthalene disulfonic acid was placed in this finish bath. This additive amounted to 0.1 percent by weight of the fiber. These fibers were not bleached and were divided into two parts, one being subjected to ultra-violet light and the second part being unexposed to ultra-violet light. The fibers were then tested in the recording spectrophotometer, manufactured by General Electric Company, and it was determined that the fibers which had been exposed to ultra-violet light had a lightness of 84.
  • the fibers unexposed to ultra-violet light had a lightness of 83.7.
  • the fibers which had been exposed to ultra-violet light had a purity of 4.4 and the fibers which were unexposed to ultra-violet light had a purity of 5.6.
  • These readings were compared to a control sample which was unbleached and also had no special stabilizing additive.
  • the control samples which were unexposed to ultra-violet light showed a lightness of 81.6 and the fibers which were exposed to ultra-violet light of the control sample had a lightness of 82.2.
  • the control fibers which were exposed to ultra-violet light had a purity of 5.8 and the fibers which were unexposed to ultra-violet light had a purity of 7.1.
  • the fibers which were unbleached and had the special stabilizing additive added to their finish bath showed a marked improvement over the control fibers concerning their lightness and purity whether they were exposed to their ultra-violet light or were not exposed to ultra-violet light.
  • acrylic fibers produced by any conventional spinning method showed a marked improvement in their stability to ultraviolet light as to their lightness and purity. This is true concerning both the unbleached fibers and the bleached fibers when they have been treated with the special stabilizing additive while still in the gel state. This will aid greatly in permitting the use of these acrylic fibers in manufacturing yarns of natural color or yarns which will be dyed with the light pastel shades.
  • a method for stabilizing synthetic linear fibers against ultra-violet light comprising treating said fibers during their spinning with a member selected from the group consisting of the naphthalene disulfonic acids and the alkali metal salts of the naphthalene disulfonic acids.
  • a method for stabilizing acrylic fibers against degradation due to ultra-violet light comprising treating said fibers with a: member selected from the group consisting of the naphthalene disulfonic acids and the alkali metal salts of the naphthalene disulfonic acids during their spin- IllIlg operation.
  • a method for stabilizing fibers composed of at least percent acrylonitr-ile and up to 20 percent of another mono-olefinic monomer copolymerizable therewith against degradation due to ultra-violet light comprising treating said fiber with a member selected from the group consisting of the naphthalene disulfonic acids and the alkali metal salts of the naphthalene disulfonic acids during their spinning operation.
  • a method for stabilizing fibers composed of 94 percent acrylonitrile and 6 percent vinyl acetate against degradation due to ultra-violet light comprising treating said fibers with a member selected from the group consisting of the naphthalene disulfonic acids and the alkali metal salts of the naphthalene disulfonic acids during their spinning operation.
  • a method for stabilizing fibers composed of a blend of two copolymers, 88 percent of the first copolymer being 94 percent acrylonitrile and 6 percent vinyl acetate and 12 percent of the second copolymer being 50 percent acrylonitrile and 50 percent methyl vinylpyridine, against degradation due to ultra-violet light comprising treating said fibers with a member selected from the group consisting of the naphthalene disulfonic acids and the alkali metal salts of the naphthalene disul-fonic acids during their spinning operation.
  • a method of stabilizing fibers composed of at least 80 percent acrylonitrile and up to 20 percent of another mono-olefinic monomer copolymerizable therewith, against degradation due to ultra-violet light comprising treating the fibers while said fibers are in a gel state with a member selected from the group consisting of naphthalene disulfonic acids and the alkali metal salts of the naphthalene disulfonic acids varying from 0.001 percent to 5 percent, based upon the weight of the fiber.
  • a method for stabilizing fibers composed of 94 percent acrylonitrile and 6 percent vinyl acetate against degradation due to ultra-violet light comprising treating said fibers during their spinning operation with 0.01 percent of 1,5, naphthalene disulfonic acid.
  • a method for stabilizing fibers composed of a blend of two copolymers 88 percent of the first copolymer be- References Cited by the Examiner UNITED STATES PATENTS 2,210,962 8/1940 Thomas 260-505 2,423,972 7/1947 Gluesenka-mp et al.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Toxicology (AREA)
  • Artificial Filaments (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Chemical Treatment Of Fibers During Manufacturing Processes (AREA)
US238736A 1962-11-19 1962-11-19 Process for treating acrylonitrile fibers with ultra-violet light stabilizer Expired - Lifetime US3281260A (en)

Priority Applications (22)

Application Number Priority Date Filing Date Title
NL300694D NL300694A (is") 1962-11-19
NL300695D NL300695A (is") 1962-11-19
US238736A US3281260A (en) 1962-11-19 1962-11-19 Process for treating acrylonitrile fibers with ultra-violet light stabilizer
GB44415/63A GB1028867A (en) 1962-11-19 1963-11-11 Method for treating synthetic polymer fibres, particularly acrylic fibres, to improve their dyeing characteristics
GB44681/63A GB1033948A (en) 1962-11-19 1963-11-12 Treating synthetic polymer fibres, particularly acrylic fibres, to improve their light stability
LU44820D LU44820A1 (is") 1962-11-19 1963-11-15
DE19631494666 DE1494666A1 (de) 1962-11-19 1963-11-15 Verfahren zur Stabilisierung von Fasern oder Faeden aus synthetischen linearen Polymerisaten,insbesondere Acrylpolymerisaten gegenueber ultraviolettem Licht
LU44821D LU44821A1 (is") 1962-11-19 1963-11-15
CH1410963A CH437623A (fr) 1962-11-19 1963-11-18 Procédé de production des fibres en polymères synthétiques linéaires stabilisées
DE19631494667 DE1494667A1 (de) 1962-11-19 1963-11-18 Verfahren zur Verbesserung der Anfaerbbarkeit von Faeden oder Fasern aus synthetischen linearen Polymerisaten,insbesondere Acrylpolymerisaten,durch basische Farbstoffe
FR954073A FR1374840A (fr) 1962-11-19 1963-11-18 Procédé pour améliorer la stabilité à la chaleur et à la lumière de fibres synthétiques, en particulier acryliques
CH1411063A CH437624A (fr) 1962-11-19 1963-11-18 Procédé de production de fibres synthétiques de polymères linéaires avec aptitude améliorée à la teinture
DK540763AA DK111038B (da) 1962-11-19 1963-11-18 Fremgangsmåde til stabilisering af vådspundne vinylpolymerfibre, især acrylonitrilpolymerfibre, mod ultraviolet lys.
SE12711/63A SE317155B (is") 1962-11-19 1963-11-18
DK540863AA DK111426B (da) 1962-11-19 1963-11-18 Fremgangsmåde til forbedring af montageligheden for basiske farvestoffer hos vådspundne fibre af syntetiske lineære vinylpolymere, især acrylonitrilpolymerfibre.
SE12710/63A SE316564B (is") 1962-11-19 1963-11-18
JP38061901A JPS4815209B1 (is") 1962-11-19 1963-11-19
BE640143A BE640143A (is") 1962-11-19 1963-11-19
BE640144A BE640144A (is") 1962-11-19 1963-11-19
FR954201A FR1374864A (fr) 1962-11-19 1963-11-19 Procédé pour améliorer l'aptitude à la teinture de fibres synthétiques, en particulier des fibres acryliques
US647241A US3402014A (en) 1962-11-19 1967-06-19 Preparation of dyeable acrylic fibers and filaments
US647242A US3380798A (en) 1962-11-19 1967-06-19 Preparation of dyeable acrylonitrile polymer fibers using 4, 4'-diaminostilbene-2, 2'-disulfonic acid

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US23878162A 1962-11-19 1962-11-19
US238736A US3281260A (en) 1962-11-19 1962-11-19 Process for treating acrylonitrile fibers with ultra-violet light stabilizer

Publications (1)

Publication Number Publication Date
US3281260A true US3281260A (en) 1966-10-25

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US238736A Expired - Lifetime US3281260A (en) 1962-11-19 1962-11-19 Process for treating acrylonitrile fibers with ultra-violet light stabilizer

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US (1) US3281260A (is")
JP (1) JPS4815209B1 (is")
BE (2) BE640143A (is")
CH (2) CH437623A (is")
DE (2) DE1494666A1 (is")
DK (2) DK111038B (is")
GB (2) GB1028867A (is")
LU (2) LU44820A1 (is")
NL (2) NL300694A (is")
SE (2) SE317155B (is")

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4020199A (en) * 1972-11-14 1977-04-26 Japan Exlan Company Limited Process for producing acrylic fibers having animal hair-like hand
EP0328119A3 (en) * 1988-02-10 1991-03-20 BASF Corporation Stabilized polyacrylonitrile fibers and method of preparation
US5674948A (en) * 1994-01-21 1997-10-07 Dsm N.V. Colored polymer composition

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3380798A (en) * 1962-11-19 1968-04-30 Monsanto Co Preparation of dyeable acrylonitrile polymer fibers using 4, 4'-diaminostilbene-2, 2'-disulfonic acid
US3718428A (en) * 1970-12-21 1973-02-27 Gaf Corp Alcoholic composition of a cationic dye-alkyl aryl sulfonic acid complex and process of dyeing therewith
JPH0219577A (ja) * 1988-07-04 1990-01-23 Nippon Saafuakutanto Kogyo Kk 反応染料用均染剤組成物

Citations (8)

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Publication number Priority date Publication date Assignee Title
US2210962A (en) * 1939-05-18 1940-08-13 Sharples Solvents Corp Sulphonic acids of aromatic compounds
US2423972A (en) * 1944-02-03 1947-07-15 Monsanto Chemicals Oleyl esters of sulphobenzoic acids
US2597708A (en) * 1948-12-30 1952-05-20 American Cyanamid Co Antistatic agent, treatment of shaped articles therewith, and treated articles
US2614289A (en) * 1947-09-04 1952-10-21 American Cyanamid Co Fiber-forming apparatus
US2626877A (en) * 1951-08-17 1953-01-27 American Cyanamid Co Treatment of articles comprising a vinyl resin with an antistatic agent and treated articles
US2626876A (en) * 1951-08-17 1953-01-27 American Cyanamid Co Antistatic treatment of articles comprising a vinyl resin and treated articles
US3095422A (en) * 1959-09-23 1963-06-25 Ciba Ltd New phenylbenzazoles
US3160665A (en) * 1957-03-06 1964-12-08 Ciba Ltd Hydroxy-benzophenones

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EP0328119A3 (en) * 1988-02-10 1991-03-20 BASF Corporation Stabilized polyacrylonitrile fibers and method of preparation
US5674948A (en) * 1994-01-21 1997-10-07 Dsm N.V. Colored polymer composition

Also Published As

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SE317155B (is") 1969-11-10
DK111038B (da) 1968-05-13
GB1033948A (en) 1966-06-22
CH437623A (fr) 1967-06-15
SE316564B (is") 1969-10-27
BE640143A (is") 1964-05-19
DK111426B (da) 1968-08-19
CH437624A (fr) 1967-06-15
NL300695A (is")
DE1494667A1 (de) 1970-12-03
GB1028867A (en) 1966-05-11
DE1494666A1 (de) 1969-12-11
NL300694A (is")
JPS4815209B1 (is") 1973-05-12
LU44820A1 (is") 1964-05-15
LU44821A1 (is") 1964-05-15
BE640144A (is") 1964-05-19

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