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US3232904A - Spin-dyed polyacrylonitrile filaments - Google Patents

Spin-dyed polyacrylonitrile filaments Download PDF

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Publication number
US3232904A
US3232904A US54365A US5436560A US3232904A US 3232904 A US3232904 A US 3232904A US 54365 A US54365 A US 54365A US 5436560 A US5436560 A US 5436560A US 3232904 A US3232904 A US 3232904A
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US
United States
Prior art keywords
spin
dyed
filaments
polyacrylonitrile filaments
solution
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 - Lifetime
Application number
US54365A
Inventor
Seibert Heinrich
Schultheiss Adam
Neufang Karl
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.)
Bayer AG
Original Assignee
Bayer AG
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Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Application granted granted Critical
Publication of US3232904A publication Critical patent/US3232904A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • D01F6/02—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
    • 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
    • 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
    • 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
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/927—Polyacrylonitrile fiber

Definitions

  • the invention relates to spin-dyed polyacrylonitrile filaments and to a process of producing the same. More particularly the process consists in dissolving in the spinning solution to be used for the production of polyacrylonitrile filaments a nigrosine base and spinning the solution by conventional methods.
  • Nigrosine bases to be used in the present process are known under the classical name Nigrosine Spirit Soluble (Colour Index, 2nd Edition, vol. 3, No. 50415 and Farbstofitabellen by Schultz, 7th Edition, page 427) and are preferably produced by heating an arylamine such as aniline, aniline salts, and nitroor nitroso benzene in the presence of iron and/or iron salts at about 180 to 200 C. They are of more or less indefinite structure.
  • the process is advantageously carried out by dissolving the afore-mentioned nigrosine bases into the vinyl polymer in dissolved state.
  • the dyestuffs are preferably dissolved in the organic solvent commonly used for spinning of the polyacrylonitrile, such as in dimetlhyl formamide.
  • the solution thus obtained is then mixed with the solution of the acrylonitrile polymer and then worked up into shaped articles, particularly into filaments and fibres respectively.
  • the new process leads to dark spin-dyed polyacrylonitrile fibres which exhibit excellent fastness properties
  • Example 15 kilograms of polyacrylonitrile and 0.150 kilogram of Nigrosine Spirit Soluble (Colour Index, 2nd Edition, No. 50415) are dissolved in kilograms of dimethylformamide and the solution is then spun in conventional manner. A deep black spin-dyed fabric is thus obtained which exhibits excellent fastness proper-ties.
  • a process for the manufacture of spin-dyed polyacrylonitrile filaments which comprises dissolving in the spinning solution to be used for the production of polyacrylonitrile filaments a nigrosine spirit soluble dyestuff and spinning the solution.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Manufacturing & Machinery (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Artificial Filaments (AREA)
  • Coloring (AREA)

Description

United States Patent 2 Claims. in. 260-41) This application is a cont-inuation-in-part of US. application Serial No. 601,121, filed July 31, 1956, now ab an doned.
The invention relates to spin-dyed polyacrylonitrile filaments and to a process of producing the same. More particularly the process consists in dissolving in the spinning solution to be used for the production of polyacrylonitrile filaments a nigrosine base and spinning the solution by conventional methods.
Nigrosine bases to be used in the present process are known under the classical name Nigrosine Spirit Soluble (Colour Index, 2nd Edition, vol. 3, No. 50415 and Farbstofitabellen by Schultz, 7th Edition, page 427) and are preferably produced by heating an arylamine such as aniline, aniline salts, and nitroor nitroso benzene in the presence of iron and/or iron salts at about 180 to 200 C. They are of more or less indefinite structure.
The process is advantageously carried out by dissolving the afore-mentioned nigrosine bases into the vinyl polymer in dissolved state. The dyestuffs are preferably dissolved in the organic solvent commonly used for spinning of the polyacrylonitrile, such as in dimetlhyl formamide. The solution thus obtained is then mixed with the solution of the acrylonitrile polymer and then worked up into shaped articles, particularly into filaments and fibres respectively.
The new process leads to dark spin-dyed polyacrylonitrile fibres which exhibit excellent fastness properties,
3,232,904 Patented Feb. 1, 1966 especially very good fastness to light and to rubbing. This result is most surprising because nigrosine bases dye polyacrylon-itrile shaped articles, such as fibres and filaments, only poor shades when applied from an aqueous dye-bath.
Example 15 kilograms of polyacrylonitrile and 0.150 kilogram of Nigrosine Spirit Soluble (Colour Index, 2nd Edition, No. 50415) are dissolved in kilograms of dimethylformamide and the solution is then spun in conventional manner. A deep black spin-dyed fabric is thus obtained which exhibits excellent fastness proper-ties.
We claim:
1. A process for the manufacture of spin-dyed polyacrylonitrile filaments which comprises dissolving in the spinning solution to be used for the production of polyacrylonitrile filaments a nigrosine spirit soluble dyestuff and spinning the solution.
2. Spin-dyed polyacrylonitrile filaments obtained according to the process of claim 1.
References Cited by the Examiner UNITED STATES PATENTS 2,531,407 3/1950 DAlelio 18-54 2,527,863 10/1950 Webb 26041 2,857,373 10/1958 Straley et a]. 855 2,941,970 6/1960 Craig 260-326 FOREIGN PATENTS 581,247 8/1959 Canada.
OTHER REFERENCES Schultz, Farbstofftabellen, 7th Edition, page 427, 1931.
MORRIS LIEBMAN, Primary Examiner.
DANIEL ARNOLD, WILLIAM H. SHORT,
ALEXANDER H. BRODMERKEL, Examiners.

Claims (2)

1. A PROCESS FOR THE MANUFACTURE OF SPIN-DYED POLYACRYLONITRILE FILAMENTS WHICH COMPRISES DISSOLVING IN THE SPINNING SOLUTION TO BE USED FOR THE PRODUCTION OF POLYACRYLONITRILE FILAMENTS A NIGROSINE SPIRIT SOLULE DYESTUFF AND SPINNING THE SOLUTION.
2. SPIN-DYED POLYACRYLONITRILE FILAMENTS OBTAINED ACCORDING TO THE PROCESS OF CLAIM 1.
US54365A 1955-08-10 1960-09-07 Spin-dyed polyacrylonitrile filaments Expired - Lifetime US3232904A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF18157A DE1109830B (en) 1955-08-10 1955-08-10 Process for the production of spun-dyed polyacrylonitrile threads

Publications (1)

Publication Number Publication Date
US3232904A true US3232904A (en) 1966-02-01

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
US54365A Expired - Lifetime US3232904A (en) 1955-08-10 1960-09-07 Spin-dyed polyacrylonitrile filaments

Country Status (4)

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US (1) US3232904A (en)
DE (1) DE1109830B (en)
FR (1) FR1155366A (en)
GB (1) GB817614A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4160760A (en) * 1977-08-22 1979-07-10 Northwestern University Process for preparing polyacrylonitrile doped with Prussion blue
US4557732A (en) * 1978-05-26 1985-12-10 Hoechst Aktiengesellschaft Process for spin-dyeing of acid-modified polymers of acrylonitrile by the wet-spinning procedure using quaternary ammonium or cyclammonium dyestuffs of low M value and high cation weight having two or three said ammonium or cyclammonium groups
US4607071A (en) * 1978-05-26 1986-08-19 Hoechst Aktiengesellschaft Process for spin-dyeing of acid-modified polymers of copolymers of acrylonitrile using rapid-fixing di-quaternary cationic dyes
US4663365A (en) * 1984-08-18 1987-05-05 Bayer Aktiengesellschaft Wash-resistant, antimicrobially-active fibres and threads and their manufacture
US20110233810A1 (en) * 2010-03-25 2011-09-29 W. M. Barr & Company Antimicrobial plastic compositions and methods for preparing same
CN103590192A (en) * 2013-10-15 2014-02-19 浙江三志纺织有限公司 Preparation method of dispersible blue 2BLN/ polyacrylonitrile-based colored nanofiber membrane

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11724386B2 (en) 2019-05-27 2023-08-15 Ati Industrial Automation, Inc. Robotic tool holder with passive compliance

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2527863A (en) * 1947-08-29 1950-10-31 Du Pont Modification and dyeing of acrylonitrile polymers
US2531407A (en) * 1946-10-25 1950-11-28 Ind Rayon Corp N,n-dimethyl acetamide-containing compositions
US2857373A (en) * 1955-03-01 1958-10-21 Eastman Kodak Co Benzothiazole azo compounds containing a reactive methylene coupling component
CA581247A (en) * 1959-08-11 Ciba Limited Shaped structures of acrylonitrile polymers with dyes of the group of the indulines and nigrosines
US2941970A (en) * 1955-06-08 1960-06-21 Chemstrand Corp Method for dispersion of pigments in acrylonitrile polymer solutions

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE506178A (en) * 1950-11-13
US2701801A (en) * 1953-10-09 1955-02-08 Du Pont Nu-substituted diamino anthraquinone dicarboximide dyes

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA581247A (en) * 1959-08-11 Ciba Limited Shaped structures of acrylonitrile polymers with dyes of the group of the indulines and nigrosines
US2531407A (en) * 1946-10-25 1950-11-28 Ind Rayon Corp N,n-dimethyl acetamide-containing compositions
US2527863A (en) * 1947-08-29 1950-10-31 Du Pont Modification and dyeing of acrylonitrile polymers
US2857373A (en) * 1955-03-01 1958-10-21 Eastman Kodak Co Benzothiazole azo compounds containing a reactive methylene coupling component
US2941970A (en) * 1955-06-08 1960-06-21 Chemstrand Corp Method for dispersion of pigments in acrylonitrile polymer solutions

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4160760A (en) * 1977-08-22 1979-07-10 Northwestern University Process for preparing polyacrylonitrile doped with Prussion blue
US4557732A (en) * 1978-05-26 1985-12-10 Hoechst Aktiengesellschaft Process for spin-dyeing of acid-modified polymers of acrylonitrile by the wet-spinning procedure using quaternary ammonium or cyclammonium dyestuffs of low M value and high cation weight having two or three said ammonium or cyclammonium groups
US4607071A (en) * 1978-05-26 1986-08-19 Hoechst Aktiengesellschaft Process for spin-dyeing of acid-modified polymers of copolymers of acrylonitrile using rapid-fixing di-quaternary cationic dyes
US4663365A (en) * 1984-08-18 1987-05-05 Bayer Aktiengesellschaft Wash-resistant, antimicrobially-active fibres and threads and their manufacture
US20110233810A1 (en) * 2010-03-25 2011-09-29 W. M. Barr & Company Antimicrobial plastic compositions and methods for preparing same
CN103590192A (en) * 2013-10-15 2014-02-19 浙江三志纺织有限公司 Preparation method of dispersible blue 2BLN/ polyacrylonitrile-based colored nanofiber membrane
CN103590192B (en) * 2013-10-15 2016-01-06 浙江三志纺织有限公司 The coloured nanofiber membrane preparation method of Disperse Blue 2BLN/polyacrylonitrile-radical

Also Published As

Publication number Publication date
DE1109830B (en) 1961-06-29
GB817614A (en) 1959-08-06
FR1155366A (en) 1958-04-25

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