US3148935A - Dyeing textile material consisting of polyacrylonitrile and its copolymers - Google Patents

Dyeing textile material consisting of polyacrylonitrile and its copolymers Download PDF

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US3148935A
US3148935A US587503A US58750356A US3148935A US 3148935 A US3148935 A US 3148935A US 587503 A US587503 A US 587503A US 58750356 A US58750356 A US 58750356A US 3148935 A US3148935 A US 3148935A
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parts
dyeing
polyacrylonitrile
copolymers
textile material
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US587503A
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Pfitzner Helmut
Baumann Hans
Eisele Julius
Federkiel Wilhelm
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BASF SE
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BASF SE
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    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino 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
    • D06P3/70—Material containing nitrile groups
    • D06P3/76—Material containing nitrile groups using basic 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

  • textile material consisting of polyacrylonitrile and its copolymers can be dyed very fast, brilliant shades by using as the dyestuffs basic dyestuffs of the general formula in which R represents an alkyl, aralkyl, aryl or cycloalkyl group, n is zero or 1, X represents a divalent atom or a divalent group which makes up the nitrogen-containing ring to a five-membered or six-membered ring, Y is the radical of an aromatic amine or enamine capable of being azo-coupled and Z is an anion.
  • R represents an alkyl, aralkyl, aryl or cycloalkyl group
  • n is zero or 1
  • X represents a divalent atom or a divalent group which makes up the nitrogen-containing ring to a five-membered or six-membered ring
  • Y is the radical of an aromatic amine or enamine capable of being azo-coupled
  • Z is an anion
  • flocks, fibres, threads, filaments, bands and woven or knitted fabrics of pure polyacrylonitrile or of copolymers of acrylonitrile with other vinyl compounds, such as vinyl chlorides, vinylidene chloride, vinyl fluoride, vinyl acetate, vinyl propionate, vinylpyridine, vinylirnidazole, vinyl alcohol, acrylic acid esters, methacrylic acid esters and/or acrylamides, said copolymers containing above about 40 percent and preferably at least 75 percent (by weight) of acrylonitrile.
  • vinyl chlorides vinylidene chloride, vinyl fluoride, vinyl acetate, vinyl propionate, vinylpyridine, vinylirnidazole, vinyl alcohol, acrylic acid esters, methacrylic acid esters and/or acrylamides
  • the dyeing can be carried out eitherin an acid bath or in a neutral or weakly alkaline bath, because the basic dyestuffs of the said kind in general undergo no appreciable change in shade of color upon variation in the pH-value.
  • the baths are in general best exhausted at weakly acid pH-values.
  • the most favorable dyeing temperatures vary according to the material to be dyed. In general the material is entered into the dyebath at about 40 to C. and dyeing effected at the boil; however it is possible to dye under static pressure at more than C., for example at to C.
  • the co-employment of the usual dyeing assistants is sometimes advantageous but usually unnecessary.
  • the dyestufis can also be added to spinning solutions which contain polyacrylonitrile or copolymers of acrylonitrile with other vinyl compounds.
  • the spun-dyed structures thereby obtained can be further dyed or shaded if desired with any desired dyestuffs, in particular those herein specified, in aqueous baths.
  • the dyeings obtained are distinguished by vivid, powerful shades and very good to excellent fastness, in particular in many cases by a fastness to light hitherto unattainable on polyacrylonitrile.
  • Example 1 A fabric of 100 parts of polyacrylonitrile fibres is in troduced at about 50 C. into a dyebath containing in 4000 parts of water 0.7 part of the dyestulf of the formula and 5 parts of 30 percent acetic acid. The whole is heated during the course of about 30 minutes to the'boiling temperature and dyeing continued for 90 minutes in the boiling bath. The fabric is then rinsed and dried. A powerful, very level, pure blue dyeing of excellent properties is obtained.
  • acetic acid for example 3.6 parts of 96 percent sulfuricacid may also be used. When dyeing from a neutral bath, somewhat less dyestuff is taken up.
  • Dyeing can be effected in an analogous manner with the other dyestufls in the table in Example 1.
  • Example 3 100 parts .of pure polyacrylonitrile monofil are dyed in a pressure vessel for 60 minutes at 125 C. with a solution of 0.8 part of the dyestuif of the formula in 2000 parts of water with the addition of 5 parts of 30 percent acetic acid. A powerful pure blue dyeing of excellent fastness is obtained.
  • Example 4 To a spinning solution, consisting of a solution of 1000 parts of polyacrylonitrile in the necessary amount of dimethylforrnamide, there is added a solution of 10 parts of the dyestuff of the formula I om-omon fibres dyed fast bluish red are obtained.
  • the fibrous material is dyed pure blue; the dyeing is extremely fast.
  • Example 6 parts of fibrous material of a copolymer of 90 percent of acrylonitrile, 5 percent of vinyl acetate and 5 percent vinylpyridine are dyed for 90 minutes at the boiling temperature in a bath containing in 2000 parts of water 3 parts of 96 percent sulfuric acid, 2 parts of the reaction product of 25 mols of ethylene oxide on 1 mol of octadecyl alcohol and 1 part of the basic azo dyestufl obtained by reacting 18 parts of the dyestulf of the formula N-NH HOOCC ⁇ /CH;
  • Example 7 and N-N-CH Polyacrylomtrile fibres are dyed in the manner described in Example 1 with the dyestuffs enumerated in the H09 following table, the dyeings therein listed being thereby 5 I obtained. All the dyeings are very level, powerful and CH; extremely fast to light: and Z represents an anion.
  • the colored textile material of claim 1 in Vt the dyestulf has the formula:

Description

United States Patent 3,148,935 DYEING TEXTILE MATERIAL CONSISTING 0F POLYACRYLONITRILE AND ITS COPOLYMERS Helmut Pfitzner, Hans Baumann, and Julius Eisele, Ludwigshafen (Rhine), and Wilhelm Federkiel, Frankentha], Pfalz, Germany, assignors to Badische Anllin- & Soda Fabrik Aktiengesellschaft, Ludwigshafen (Rhine), Germany No Drawing. Filed May 28, 1956, Ser. No. 587,503 Claims priority, application Germany June 25, 1955 3 Claims. (Cl. 8-41) This invention relates to an improved process of dyeing textile material consisting of polyacrylonitrile and its copolymers.
We have found that textile material consisting of polyacrylonitrile and its copolymers can be dyed very fast, brilliant shades by using as the dyestuffs basic dyestuffs of the general formula in which R represents an alkyl, aralkyl, aryl or cycloalkyl group, n is zero or 1, X represents a divalent atom or a divalent group which makes up the nitrogen-containing ring to a five-membered or six-membered ring, Y is the radical of an aromatic amine or enamine capable of being azo-coupled and Z is an anion.
A compound of this kind is already known (cf. Glauert, J. Chem. Soc. London, 195 3, 3742); other members are obtained for example by oxidizing condensation of hydrazones of heterocyclic ketones of the general formula RN (CH=CH u C=N NH3 in which R, n and X have the above significance, with aromatic amines or enamines capable of being azo-coupled in acid medium, or by allowing alkylating agents to act on dyestuffs free from sulfonic acid groups of the general formula in which n, X and Y also have the above significance.
For dyeing with the basic dyestuffs of the said kind there are especially suitable flocks, fibres, threads, filaments, bands and woven or knitted fabrics of pure polyacrylonitrile or of copolymers of acrylonitrile with other vinyl compounds, such as vinyl chlorides, vinylidene chloride, vinyl fluoride, vinyl acetate, vinyl propionate, vinylpyridine, vinylirnidazole, vinyl alcohol, acrylic acid esters, methacrylic acid esters and/or acrylamides, said copolymers containing above about 40 percent and preferably at least 75 percent (by weight) of acrylonitrile.
In principle, the dyeing can be carried out eitherin an acid bath or in a neutral or weakly alkaline bath, because the basic dyestuffs of the said kind in general undergo no appreciable change in shade of color upon variation in the pH-value.
Consequently the pH-value may also be changed during the dyeing, and this may be advantageous in some cases. The baths are in general best exhausted at weakly acid pH-values. The most favorable dyeing temperatures vary according to the material to be dyed. In general the material is entered into the dyebath at about 40 to C. and dyeing effected at the boil; however it is possible to dye under static pressure at more than C., for example at to C. The co-employment of the usual dyeing assistants is sometimes advantageous but usually unnecessary.
The dyestufis can also be added to spinning solutions which contain polyacrylonitrile or copolymers of acrylonitrile with other vinyl compounds. The spun-dyed structures thereby obtained can be further dyed or shaded if desired with any desired dyestuffs, in particular those herein specified, in aqueous baths.
The dyeings obtained are distinguished by vivid, powerful shades and very good to excellent fastness, in particular in many cases by a fastness to light hitherto unattainable on polyacrylonitrile.
The following examples will further illustrate this invention but the invention is not restricted to these examples. The parts specified are parts by weight.
Example 1 A fabric of 100 parts of polyacrylonitrile fibres is in troduced at about 50 C. into a dyebath containing in 4000 parts of water 0.7 part of the dyestulf of the formula and 5 parts of 30 percent acetic acid. The whole is heated during the course of about 30 minutes to the'boiling temperature and dyeing continued for 90 minutes in the boiling bath. The fabric is then rinsed and dried. A powerful, very level, pure blue dyeing of excellent properties is obtained.
Instead of acetic acid, for example 3.6 parts of 96 percent sulfuricacid may also be used. When dyeing from a neutral bath, somewhat less dyestuff is taken up.
If the dyeing is commenced in a weak ammoniacal bath and continued with the gradual addition of small amounts of acetic or sulfuric acid, very powerful dyeings are obtained with extensive exhaustion of the dyebath.
For the dyeing there may be used in an analogous manner the dyestuffs set out in the following table, which also indicates the shade of color obtained:
Example 2 100 parts of a fabric of a copolymer of 95 percent of acrylonitrile and 5 percent of butyl methacrylate are dyed in the manner described in Example 1 with a dyebath which consists of a solution of 0.8 part of the dyestuff 5 of the formula CgHgO C-N=N-C- c1- N+ cam-c (EH in 4000 parts of water. A very fast red-violet dyeing is obtained.
Dyeing can be effected in an analogous manner with the other dyestufls in the table in Example 1.
Example 3 100 parts .of pure polyacrylonitrile monofil are dyed in a pressure vessel for 60 minutes at 125 C. with a solution of 0.8 part of the dyestuif of the formula in 2000 parts of water with the addition of 5 parts of 30 percent acetic acid. A powerful pure blue dyeing of excellent fastness is obtained.
Example 4 To a spinning solution, consisting of a solution of 1000 parts of polyacrylonitrile in the necessary amount of dimethylforrnamide, there is added a solution of 10 parts of the dyestuff of the formula I om-omon fibres dyed fast bluish red are obtained.
Example 5 100 parts of fibres of a copolymer of 40 parts of acrylonitrile and 60 parts of vinyl chloride are moved for minutes at 85 C. in a dyebath which contains, in 3000 75 6 parts of water, 07 part of the dyestulf of the formula c H CzH5O- 4 CN=:NN Br C4 n N1- I (12Hls 5 parts of 30 percent acetic acid and 3 parts of the reaction product of 24 mols of ethylene oxide on 1 mol of sperm oil alcohol. The fibrous material is dyed pure blue; the dyeing is extremely fast.
Example 6 parts of fibrous material of a copolymer of 90 percent of acrylonitrile, 5 percent of vinyl acetate and 5 percent vinylpyridine are dyed for 90 minutes at the boiling temperature in a bath containing in 2000 parts of water 3 parts of 96 percent sulfuric acid, 2 parts of the reaction product of 25 mols of ethylene oxide on 1 mol of octadecyl alcohol and 1 part of the basic azo dyestufl obtained by reacting 18 parts of the dyestulf of the formula N-NH HOOCC\ /CH;
with 35 parts of dimethyl sulfate in 200 parts of dimethylformamide at C.
A powerful pure red dyeing of very good fastness to light and good fastness to moisture is obtained.
By using for the dyeing 0.8 part of the dyestuff of the formula there is similarly obtained a very fast bluish green dyeing.
With the basic dyestuif obtainable by reacting with dimethyl sulfate the dyestuff of the formula clear, fast reddish yellow dyeings are obtained in analogous manner.
3,148,935 7 8 Example 7 and N-N-CH; Polyacrylomtrile fibres are dyed in the manner described in Example 1 with the dyestuffs enumerated in the H09 following table, the dyeings therein listed being thereby 5 I obtained. All the dyeings are very level, powerful and CH; extremely fast to light: and Z represents an anion.
Dyeing on Dyestufl fibres t polyacrylonltrile "OrN''fi-- I /CHs HC\ o-N=N- N\ 010. Blue.
N+/ CHa l CHE CH3 H CLHQ ll OgN C CN=N N ClOr D0 I CA r CH; it?
HG cN=Nc Cl- Red.
Cm 1150f N L Ha OaN(||3-? 13305-0 CN=NG- CIh-O-SOr Do.
\ e u 0 CH HEGQ/ \N J I CH;
- H H3--s NCC -N=N-C- 01- Do \N+ I HO H%-S /C:H
FaC-C\ (JN= N\ clor Blue.
N+/ Cr b L 01 What we claim is: 2. The colored textile material of claim 1 in v 1. A textile material comprising an acrylonitrile pothe dyestufi has the formula: lymer containing at least 40% by weight of acrylonitrile which is colored with a basic cationic dyestufi of the formula: H0 8 Q ll no e-N=N-o N--CH 01 80 \g/ 0 AN=NC/ N-cH, 2 CH1 I 3. The colored textile material of claim 1 in Vt the dyestulf has the formula:
wherein A represents a member selected from the class consisting of g N=GN=NC N-cH. onioso Br": J- \&B% I
0H; (References on following page) 10 References Cited in the file of this patent OTHER REFERENCES UNITED STATES PATENTS American Dyestufi Reporter for November 23, 1953, 2,726,237 Towne Dec. 6, 1955 PP- P792, P793- 2,764,466 Bidgood Sept. 25, 1956 American Dyestuif Reporter for January 19, 1953, p. 2,768,054 Armento Oct. 23, 1956 5 P42. 2,772,943 Hiller Dec. 4, 1956 Glauert: J. Chem. Soc., London, 1953, p. 3742. (Copy 2,815,338 Ruegg D60- 3, 1957 in P.O.S.L. and ordered for 8/55AB.) 2,832,764 Huenig April 29, 1958 2,893,816 Tsang July 7, 1959

Claims (1)

1. A TEXTILE MATERIAL COMPRISING AN ACRYLONITRILE POLYMER CONTAINING AT LEAST 40% BY WEIGHT OF ACRYLONITRILE WHICH IS COLORED WITH A BASIC CATIONIC DYESTUFF OF THE FORMULA:
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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3291788A (en) * 1965-09-27 1966-12-13 Mitsubishi Chem Ind Cationic triazole disazo dyestuffs
US3332932A (en) * 1964-08-14 1967-07-25 Interchem Corp Monoazo pigments of diazotized 3-amino-4-methylbenzamide with naphthols
DE1619328B1 (en) * 1966-03-10 1970-02-26 Basf Ag Use of a quaternized benzothiazole azo dye for dyeing textile materials made of polyacrylonitrile
US3515715A (en) * 1967-01-23 1970-06-02 Eastman Kodak Co Quaternized pyrazolylazo dyes
US4028321A (en) * 1973-07-27 1977-06-07 Hoechst Aktiengesellschaft Basic azo amino-phenylene dyestuffs
US4085098A (en) * 1972-07-31 1978-04-18 Sandoz Ltd. Azo dyes containing a heterocyclic ring having a quaternized nitrogen atom and at least one optionally substituted phenoxyalkyl or naphthyloxyalkyl substituent
US4111929A (en) * 1975-07-11 1978-09-05 Imperial Chemical Industries Limited Tetrahydroquinoline azo triazole dyestuffs
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
US4754022A (en) * 1984-11-13 1988-06-28 Ciba-Geigy Corporation Cationic dyes from diazotized 5-aminoisothiazoles and tetrahydroquinolines or indolines
US4818815A (en) * 1985-07-26 1989-04-04 Ciba-Geigy Corporation Cationic 1,2,3-thiadiazole-azo-aniline or tetrahydroquinoline compounds
US4997918A (en) * 1982-08-30 1991-03-05 Ciba-Geigy Corporation Benzthiazolium azo dyes
US5929216A (en) * 1989-12-06 1999-07-27 Ciba Specialty Chemicals Corporation Benzothiazolium containing azo dyes useful for dyeing polyacrylonitrile

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2726237A (en) * 1952-08-16 1955-12-06 Eastman Kodak Co Azo-2-amino-4-trifluoromethylthiazoles
US2764466A (en) * 1952-08-28 1956-09-25 Du Pont Process for dyeing a wool-acrylonitrile fiber mixture
US2768054A (en) * 1952-12-30 1956-10-23 Gen Aniline & Film Corp Process of making acetate dyestuff powders
US2772943A (en) * 1956-12-04 Process of dyeing wool-polyacrylo-
US2815338A (en) * 1954-05-13 1957-12-03 Ciba Ltd Basic azo dyestuffs
US2832764A (en) * 1955-03-31 1958-04-29 Basf Ag Production of azo dyestuffs
US2893816A (en) * 1957-03-01 1959-07-07 American Cyanamid Co Polyacrylonitriles dyed with quaternized heterocyclic azo dyes

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2772943A (en) * 1956-12-04 Process of dyeing wool-polyacrylo-
US2726237A (en) * 1952-08-16 1955-12-06 Eastman Kodak Co Azo-2-amino-4-trifluoromethylthiazoles
US2764466A (en) * 1952-08-28 1956-09-25 Du Pont Process for dyeing a wool-acrylonitrile fiber mixture
US2768054A (en) * 1952-12-30 1956-10-23 Gen Aniline & Film Corp Process of making acetate dyestuff powders
US2815338A (en) * 1954-05-13 1957-12-03 Ciba Ltd Basic azo dyestuffs
US2832764A (en) * 1955-03-31 1958-04-29 Basf Ag Production of azo dyestuffs
US2893816A (en) * 1957-03-01 1959-07-07 American Cyanamid Co Polyacrylonitriles dyed with quaternized heterocyclic azo dyes

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3332932A (en) * 1964-08-14 1967-07-25 Interchem Corp Monoazo pigments of diazotized 3-amino-4-methylbenzamide with naphthols
US3291788A (en) * 1965-09-27 1966-12-13 Mitsubishi Chem Ind Cationic triazole disazo dyestuffs
DE1619328B1 (en) * 1966-03-10 1970-02-26 Basf Ag Use of a quaternized benzothiazole azo dye for dyeing textile materials made of polyacrylonitrile
US3515715A (en) * 1967-01-23 1970-06-02 Eastman Kodak Co Quaternized pyrazolylazo dyes
US4085098A (en) * 1972-07-31 1978-04-18 Sandoz Ltd. Azo dyes containing a heterocyclic ring having a quaternized nitrogen atom and at least one optionally substituted phenoxyalkyl or naphthyloxyalkyl substituent
US4028321A (en) * 1973-07-27 1977-06-07 Hoechst Aktiengesellschaft Basic azo amino-phenylene dyestuffs
US4111929A (en) * 1975-07-11 1978-09-05 Imperial Chemical Industries Limited Tetrahydroquinoline azo triazole dyestuffs
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
US4997918A (en) * 1982-08-30 1991-03-05 Ciba-Geigy Corporation Benzthiazolium azo dyes
US4754022A (en) * 1984-11-13 1988-06-28 Ciba-Geigy Corporation Cationic dyes from diazotized 5-aminoisothiazoles and tetrahydroquinolines or indolines
US4818815A (en) * 1985-07-26 1989-04-04 Ciba-Geigy Corporation Cationic 1,2,3-thiadiazole-azo-aniline or tetrahydroquinoline compounds
US5929216A (en) * 1989-12-06 1999-07-27 Ciba Specialty Chemicals Corporation Benzothiazolium containing azo dyes useful for dyeing polyacrylonitrile

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