US3097044A - Process for coloring polypropylene - Google Patents

Process for coloring polypropylene Download PDF

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Publication number
US3097044A
US3097044A US19471A US1947160A US3097044A US 3097044 A US3097044 A US 3097044A US 19471 A US19471 A US 19471A US 1947160 A US1947160 A US 1947160A US 3097044 A US3097044 A US 3097044A
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Prior art keywords
mordant
fiber
dye
bath
weight
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US19471A
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English (en)
Inventor
Skeuse Thomas
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Novartis Corp
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Geigy Chemical Corp
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Priority to US19471A priority Critical patent/US3097044A/en
Priority to CH323361A priority patent/CH371088A/de
Priority to CH323361D priority patent/CH323361A4/de
Priority to GB11656/61A priority patent/GB921975A/en
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    • 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
    • D06P3/79—Polyolefins
    • D06P3/795—Polyolefins using metallisable or mordant dyes, dyeing premetallised fibres
    • 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
    • Y10S8/928—Polyolefin fiber

Definitions

  • This invention relates to a method of coloring polypropylene, especially fibers of polypropylene.
  • fibers of polypropylene could not be colored commercially, since attempted dyeings and paddings were obtained with poor color value and/ or poor light tastness properties.
  • polypropylene can be dyed and padded successfully using mordant dyes by the method of the present invention.
  • the method of the invention involves the process, which requires the simultaneous interaction of dye, metal salt, acid and fiber in the dye bath.
  • Any mordant dye which is amenable to the process is within the scope of the present invention.
  • Other metal salts besides chrome salts may be used, e.g. cobalt, nickel, etc. salts are useful.
  • the dyes usable according to the present invention are the known dyes which are capable of combining with various metals preferably with chromium, to form metal complexes. Such dyes are known in the art as mordant dyes.
  • mordant dyes are all characterized by a salt-forming group and a group capable of forming a coordinated compound with a metallic atom in such relative position that an internal complex salt can be produced. Conditions for the formation of heterocyclic 5- or 6-membered rings favor the production of such complexes.
  • Mordant dyes are represented in almost all dye classes such as nitnoso dyes, mono-azo dyes, disazo dyes Examples of specific dyestufis usable Index of the American Association of Textile Chemists and Colorists, 2nd edition, vol. 1, pp. 1405, ft.
  • Acid Red 12 (mordant dye: chrome in dye bath); Mordant Blacks 1, 3, 5, 9, 11, 13, 17, 20, 24, 26, 32, 33, 38; Mordant Blues 1, 3, 7, 9, 13, 37, 47, 49, 55; Mordant Browns 1, 4, 17, 19, 23, 33, 35, 40, 50, 63; Mordant Greens 5, 9, 15, 26, 30; Mordant Oranges 1, 5, 6, 8, 18; Mordant Reds 5, 7, 9, 12, 17, 19, 20, 21, 36, 37; Mordant Violets l, 5, 16, 28, 30; and Mordant Yellows 1, 3, 5, 14, 20, 26, 30, 38.
  • the method of the invention is not limited to a process for the dyeing of polypropylene fiber, but also within the scope of the invention is the padding of polypropylene fiber.
  • the dyeing operation includes the step which comprises contacting polypropylene fibers in an aqueous acid bath with a mordant dye as described above, in presence of a water-soluble metal salt at a temperature of about 212 F. under normal atmospheric pressure for a period of from about 15 minutes to about minutes.
  • An optional additional component of the dye bath comprises an organic solvent which is miscible in said dye bath and which is described more in detail hereinbelow. Said organic solvent, in a specific embodiment of the invention, is employed in a concentration of from about 0.5% to about 5% by weight, preferably about 2% by weight based on total weight of dye bath.
  • the dye bath contains an acid, more fully described hereinbelow, in a concentration of from about 2% to about 5% by weight based on dry weight of polypropylene fiber.
  • an acid more fully described hereinbelow
  • the liquor ratio of the dye bath to polypropylene fiber ranges from about 8 parts by Weight of dye bath to 1 part by weight of dry fiber, to 30 parts by weight of dye bath to 1 part by weight of dry fiber.
  • the contact time in another specific embodiment of the invention is from about 15 minutes to about 90 minutes.
  • polypropylene fiber is contacted in an aqueous acid bath with a mordant dye in presence of the Water-soluble metal salt at a temperature of from about 213 F. to about 250 F. under super atmospheric pressure suflicient to maintain the bath as a liquid for a period of from about 15 minutes to about 90 minutes.
  • the polypropylene fiber is contacted in said bath which also contains an organic solvent, more fully described hereinbelow.
  • polypropylene fiber is contacted in an aqueous bath, having from about 2% to about 5% by weight of acid and from about 0.5% to about 6% by weight, based on total weight of dye bath, preferably about 2%, of benzyl alcohol as organic solvent, said bath also containing from about 0.5 to about 5% by weight of a water-soluble chrominum salt and from about 0.1% to about 10% by weight of a mordant dye at from about 213 F. to about 250 F. under super-atmospheric pressure, suflicient to maintain the bath as a liquid, for from about 15 minutes to about 90 minutes, all of said percentages by weight being based on the dry weight of said fiber, except that of the organic solvent.
  • polypropylene fiber is padded in a method which comprises first contacting said fiber in an aqueous acid bath with a mordant dye in presence of a water-soluble metal salt, preferably a chrome salt, at a temperature of from about F. to about 180 F. under normal atmospheric pressure, then removing the wet fiber from said bath, and finally steaming said wet fiber under super-atmospheric pressure, preferably from about 8 lbs. per square inch to about 15 lbs. per square inch, for a period of from about 15 minutes to about 90 minutes.
  • a water-soluble metal salt preferably a chrome salt
  • the method of padding polypropylene according to the invention may also be practiced with from about 0.5 by weight to about 5% by a weight, preferably about 2% by weight (based on total :eight of padding solution) of the organic solvent, e.g. benzyl alcohol, described hereinabovc.
  • the organic solvent e.g. benzyl alcohol, described hereinabovc.
  • the acid employed is any suitable acid which is soluble in water and not appreciably harmful to the material to be dyed.
  • mineral acids such as sulphuric acid are sometimes used.
  • certain organic acids for example the lower alkanoic acids such as e.g. formic acid, acetic acid, propionic acid, butyric acid, etc.
  • the known metachrome process for dyeing wool does not involve an acid bath. See, for example, Diserens, L., The Chemical Technology of Dyeing and Printing, translated and revised from the 2nd German ed. by P. Wengraf and H. P. Baumann, vol. 1, especially pages 460 and 461, New York (Reinhold, 1951).
  • polypropylene fiber is understood to embrace not merely raw stock, tow, or individual strands of polypropylene, but also is meant to include piece goods I and any other form of textile stuff.
  • mordant dye that is, a dye fully capable of forming a complex with a watersoluble metal salt.
  • mordant dyestutf especially useful in dyeing polypropylene is mordant dye used with water-soluble chromium salts which has been described and illustrated hereinabove. It is understood, however, that any suitable water-soluble metal salt is within the scope of invention: in particular, e.g. the water-soluble chromium salts such as alkali metal chromium salts, e.g. sodium chromates, potassium chromates, ammonium chromates, etc.
  • soluble alkaline earth metal chromates e.g. calcium chromates, magnesium chromates, etc.
  • chromium halides especially chromium fluoride, chromium chloride, etc., and chromium low alkanoates, preferably chromium formate, chromium acetate, chromium propionate, etc.
  • concentration of the water-soluble metal salt is advantageously from about 0.5% to about 6% by weight based on the dry weight of the fiber. It is often useful and convenient to employ the same weight percent of chromium salt as dyestuff.
  • the concentration of dyestutf in general, ranges from about 0.1% to about by weight, preferably from about 0.5% to about 4% by Weight, based on the dry weight of fiber.
  • the optional organic solvent which is useful according to the present invention comprises certain organic alcohols, ethers, ketones and combinations thereof. Aromatic as well as aliphatic type solvents are included within the scope of the term organic solvent. Such organic solvent must be readily soluble in water and must have the property of opening up the fiber, thus facilitating the coloring operation with the result that better exhaustion and higher color yields are obtained.
  • organic solvents illustrate some of the preferred solvents for use in the present invention, however, other solvents will be apparent from the foregoing, to the skilled textile chemist. It is not intended, therefore, to limit the scope of this invention to those solvents specifically mentioned, i.e.
  • benzyl alcohol cyclohexanol, propyl alcohol, butyl alcohol, furfuryl alcohol, isophorone, acetophenone, ethylene glycol, phenyl ether, butyl Cellosolve, phenyl Cellosolve, furfural, paraldehyde, n-butyl acetate.
  • the polypropylene fiber is contacted with the aqueous padding liquor at about 120 F. to about 180 F. for a time sufiicient to impregnate the fiber with the dye liquor.
  • the time of 5 contact is not critical.
  • the wet impregnated fiber is subjected to steaming at super-atmospheric pressure, preferably from about 8 lbs. per square inch to about lbs. per square inch.
  • the dyed polypropylene is washed, e.g. with cold water.
  • the contact time is generally from about 15 minutes to about 90 minutes, preferably from about 45 minutes to about 60 minutes.
  • the contact time also is generally from about 15 minutes to about 90 minutes, preferably from about 45 minutes to about 60 minutes.
  • the liquor ratio i.e. the relationship between weight of dye bath and weight of fiber to be dyed, is in the range of from about 8 parts dye bath to one part fiber, to about 30 parts dye bath to 1 part fiber.
  • a liquor ratio of about to 1, to to 1 has been found to be satisfactory.
  • the liquor ratio is advantageously 15 to 1, to 10 to 1 and may also be 8 to 1.
  • parts and percentages are by weight, based on the dry Weight of fiber. The relationship of parts by weight to parts by volume is as that of grams to cubic centimeters. Temperatures are in degrees Fahrenheit.
  • Example 1 said solution.
  • the padding is carried out at 120 at the rate of yards per minute of fiber, after which the padded fibers, without drying, are transferred to a steam chamber and steamed under 15 lbs. pressure for 4-5 minutes.
  • True shade development occurs during the steaming operation in which C.-I. Mordant Violet 1 changes from a weak, dull, reddish violet, to a bright violet.
  • Example 3 A dye bath is prepared containing an aqueous solution of 2% Cl. Mordant Yellow 5, 4% sodium bichromate and 3% acetic acid, said bath having a liquor ratio of 30 parts dye solution to 1 part of fiber.
  • the dye bath having the polypropylene fiber therein is heated during 30 minutes to 250 and held therefor 60 minutes, pressure being maintained at 18 lbs. per square inch to assure that the bath remains as a liquid.
  • the bath is then cooled to room temperature and cautiously depressurized.
  • the dyed polypropylene is removed from the bath and washed with water. True development of shade is obtained and hand wash tests at for 15 minutes with 1% soap solution in water show that the color does not lose depth. Fadeometer tests, moreover, show that all the dyed polypropylene fibers possess good light fastness properties.
  • Mordant Red 36 and 6% bichromate or 3% Cl.
  • Mordant Orange 8 and 6% bichromate or 1% Cl.
  • Mordant Blue 1 and 2% bichromate or 1.5% CI.
  • Mordant Violet 1 and 3% bichromate are used in place of the 2% Cl.
  • Mordant Yellow 5 and 4% bichromate then equally good results are obtained.
  • Example 4 A dye bath is prepared containing an aqueous solution of 1.5 C.I. Mordant Violet 1, 1.5 sodium bichromate and 3% formic acid, said ba-th having a liquor ratio of 20 parts of dye to 1 part of fiber.
  • the bath having the polypropylene fiber therein is heated to 212 over a 20 minute period and held there for 1 hour, after which the bath is cooled to room temperature and the dyed polypropylene washed with water.
  • Example 5 A dye bath is prepared containing an aqueous solution of 0.5% of Cl. Mordant Yellow 1, 0.5% of sodium bichromate, 5% of acetic acid and 2% by weight (based on total solution) of benzyl alcohol, said bath having a liquor ratio of parts dye solution to 1 part fiber.
  • the dye bath, having the polypropylene fiber therein, is heated over a 20 minute period to 212. The bath is held at 212 for 1 hours. Afterward, the bath is cooled to room temperature and the dyed polypropylene is Washed with water. Exhaustion tests with wool flannel show that most of the color is taken up by the polypropylene fiber. Good pileup and color yield is observed. If, instead of 0.5% of color and of bichromate, 3% each of color and of bichromate is employed under the same conditions, then equally good results are obtained.
  • Example 6 Polypropylene fiber is dyed in the same manner as in Example 5, except that 0.5% of CI. Mordant Blue 1 is used instead of Cl. Mordant Yellow 5. Similar results are obtained when 3% of Cl. Mordant Blue 1 is used.
  • Example 7 Polypropylene fiber is dyed in the same manner as in Example 5, except that 0.5 of Cl. Mordant Violet 1 is used instead of Cl. Mordant Yellow 5. Similar results are obtained when 3% of Cl. Mordant Violet '1 is used.
  • Example 8 Polypropylene fiber is dyed in the same manner as in Example 5, except that 0.75% of Cl. Mordant Orange 8 and 0.75% of sodium bichromate are used. Good results are also obtained with this same color if the proportion of color and also of bichromate is changed to 4%.
  • Example 9 Polypropylene fiber is dyed in the same manner as in Example 5, except that 4% of Cl Mordant Blue 55 is used as the color and the sodium bichromate is employed in the amount of 4%.
  • Example 10 Polypropylene fiber is dyed in the same manner as in Example 5 except that 2% of Cl. Mordant Black 13 is used as the color and the sodium bichromate is employed in the amount of 2%.
  • Example 11 A dye bath is prepared containing an aqueous solution of 0.5% of Cl. Mordant Yellow 5, 0.5% of sodium bichromate, 5% of acetic acid and 2% by weight (based on total weight of solution) of benzyl alcohol, said bath having a liquor ratio of parts dye solution to 1 part fiber.
  • the dye bath having the polypropylene therein is heated over a. period of 30 minutes to 250. Pressure is maintained to assure that the bath remains in the liquid state.
  • the bath is held at 25 0 for minutes and then cooled to room temperature and cautiously depressurized, after which the dyed polypropylene fiber is removed and washed with water. Exhaustion tests with wool flannel are good and excellent color yield is obtained. The shade is full, clear and very similar to that obtained on wool which has been dyed by the top chrome process.
  • Example 12 Polypropylene fiber is dyed in the same manner as in Example 11, except that 0.5 of Cl. Mordant Violet 1 is used instead of Cl. Mordant Yellow 5. Similar results are obtained when 3% of Cl. Mordant Violet 1 is used.
  • Example 14 Polypropylene fiber is dyed in the same manner as in Example 11, except that 0.75% of Cl. Mordant Orange 8 and 0.75% of sodium bichromate are used. Good results are also obtained with this same color if the proportion of color and also of bichroma-te is changed to 4%.
  • Example 15 Polypropylene fiber is dyed in the same manner as in Example 11, except that 4% of Cl. Mordant Blue 55 is used as the color and the sodium bichromate is employed in the amount of 4%
  • Example 16 Polypropylene fiber is dyed in the same manner as in Example 11, except that 2% of Cl. Mordant Black 13 is used as the color and the sodium bichromate is employed in the amount of 2%.
  • the method of dyeing polypropylene fiber by the simultaneous interaction of dye, water soluble chromium sal-t, acid and fiber in aqueous dye bath which comprises contacting said fiber in said bath with a mordant dye in presence of said water-soluble chromium salt for a period of from about 15 minutes to about minutes at a temperature of from about 212 to about 250 F., the ratio of said dye to said chromium salt ranging from about 1:1 to about 1:2 by Weight, based on the dry weight of the fiber.
  • aqueous acid dye bath also contains a minor proportion of an organic water-miscible solvent selected from the group consist-ing of benzyl alcohol, cyclohexanol, propyl alcohol, butyl alcohol, furfuryl alcohol, isophorone, acetophenone, ethylene glycol, phenylether, butyl Cellosolve, phenyl Cellosolve, furfural, paraldehyde and n-butyl acetate.
  • organic water-miscible solvent selected from the group consist-ing of benzyl alcohol, cyclohexanol, propyl alcohol, butyl alcohol, furfuryl alcohol, isophorone, acetophenone, ethylene glycol, phenylether, butyl Cellosolve, phenyl Cellosolve, furfural, paraldehyde and n-butyl acetate.
  • aqueous acid bath contains (a) from about 2% to about 5% by weight of a water-soluble acid, which ranges in strength from that of acetic acid to that of formic acid (b) from about 0.5 to about 5% by volume of benzyl alcohol,
  • aqueous acid bath contains a minor proportion of an organic water-miscible solvent, selected from the group consisting of benzyl alcohol, cy clohexanol, propyl alcohol, butyl alcohol, furfuryl alcohol, isophorone, acetophenone, ethylene glycol, phenylether, butyl Cellosolve, phenyl Cellosolve, furfural, paraldehyde and n-butyl acetate.
  • organic water-miscible solvent selected from the group consisting of benzyl alcohol, cy clohexanol, propyl alcohol, butyl alcohol, furfuryl alcohol, isophorone, acetophenone, ethylene glycol, phenylether, butyl Cellosolve, phenyl Cellosolve, furfural, paraldehyde and n-butyl acetate.
  • aqueous acid bath contains (a) from about 2% to about by weight of watersoluble acid, which ranges in strength from that of acetic to that of formic acid, (b) from about 0.5% to about 5% by volume of benzyl alcohol as additional solvent, (0) 2% by weight of a water-soluble chromium salt,
  • mordant dye is selected from. the group consisting of (a) the dyestufi of the formula (12) the dyestuff of the formula GOONs C IOONa 10 (d) the dyestuif of the formula (e) dyestufii of the formula and SO NB.
  • a colored composition of matter which consists essentially of polypropylene fiber and, as dyeing agent bound thereto a. chromium complexed mordant dye.

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  • Textile Engineering (AREA)
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US19471A 1960-04-04 1960-04-04 Process for coloring polypropylene Expired - Lifetime US3097044A (en)

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Application Number Priority Date Filing Date Title
US19471A US3097044A (en) 1960-04-04 1960-04-04 Process for coloring polypropylene
CH323361A CH371088A (de) 1960-04-04 1961-03-17 Verfahren zum Färben von Polypropylenfasern
CH323361D CH323361A4 (de) 1960-04-04 1961-03-17 Verfahren zum Färben von Polypropylenfasern
GB11656/61A GB921975A (en) 1960-04-04 1961-03-30 Process for coloring polypropylene fibres and the resulting products

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3192007A (en) * 1962-12-26 1965-06-29 Exxon Research Engineering Co Blending of polypropylene with unmetallized chelating agent to improve dyeability
US3203750A (en) * 1961-08-18 1965-08-31 Sandoz Ltd Process for dyeing shaped articles of polymers of olefinic unsaturated compounds
US3226177A (en) * 1961-12-02 1965-12-28 Mitsui Kagaku Kogyo Kabushiki Process for the dyeing of polyolefin fibrous materials
US3235322A (en) * 1962-08-10 1966-02-15 Nitto Boseki Co Ltd Dyeing of polyolefin fibers in fast colours
US3287082A (en) * 1961-05-15 1966-11-22 Eastman Kodak Co T-alkyl chromate or t-cycloalkyl chromate treated polyolefins
US3337289A (en) * 1963-12-30 1967-08-22 Du Pont Process for dyeing microporous sheet material
US3390947A (en) * 1964-06-24 1968-07-02 Gen Aniline & Film Corp Process for dyeing polyester textile materials with substituted anthraquinone dyestuffs
USB336902I5 (de) * 1972-03-07 1975-01-28
US3894840A (en) * 1972-03-07 1975-07-15 Hoechst Ag Process for the single-bath dyeing of unmodified polyolefin fibers with metal complex dyestuffs
US3894841A (en) * 1972-03-07 1975-07-15 Hoechst Ag Process for the single-bath dyeing of unmodified polyolefin fibers with water-insoluble pigment dyestuffs

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2520105A (en) * 1947-05-27 1950-08-22 American Cyanamid Co Metachrome dyeing procedure
US2534647A (en) * 1950-12-19 Single bath chrome dyeing process
GB809495A (en) * 1956-07-31 1959-02-25 Glanzstoff Ag A process for dyeing polyolefine textile materials
US2886471A (en) * 1954-03-30 1959-05-12 British Cellophane Ltd Solid polyethylene plastic materials
GB814582A (en) * 1956-07-31 1959-06-10 Glanzstoff Ag A process for dyeing polyolefine textile materials

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2534647A (en) * 1950-12-19 Single bath chrome dyeing process
US2520105A (en) * 1947-05-27 1950-08-22 American Cyanamid Co Metachrome dyeing procedure
US2886471A (en) * 1954-03-30 1959-05-12 British Cellophane Ltd Solid polyethylene plastic materials
GB809495A (en) * 1956-07-31 1959-02-25 Glanzstoff Ag A process for dyeing polyolefine textile materials
GB814582A (en) * 1956-07-31 1959-06-10 Glanzstoff Ag A process for dyeing polyolefine textile materials

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3287082A (en) * 1961-05-15 1966-11-22 Eastman Kodak Co T-alkyl chromate or t-cycloalkyl chromate treated polyolefins
US3203750A (en) * 1961-08-18 1965-08-31 Sandoz Ltd Process for dyeing shaped articles of polymers of olefinic unsaturated compounds
US3226177A (en) * 1961-12-02 1965-12-28 Mitsui Kagaku Kogyo Kabushiki Process for the dyeing of polyolefin fibrous materials
US3235322A (en) * 1962-08-10 1966-02-15 Nitto Boseki Co Ltd Dyeing of polyolefin fibers in fast colours
US3192007A (en) * 1962-12-26 1965-06-29 Exxon Research Engineering Co Blending of polypropylene with unmetallized chelating agent to improve dyeability
US3337289A (en) * 1963-12-30 1967-08-22 Du Pont Process for dyeing microporous sheet material
US3390947A (en) * 1964-06-24 1968-07-02 Gen Aniline & Film Corp Process for dyeing polyester textile materials with substituted anthraquinone dyestuffs
USB336902I5 (de) * 1972-03-07 1975-01-28
US3894840A (en) * 1972-03-07 1975-07-15 Hoechst Ag Process for the single-bath dyeing of unmodified polyolefin fibers with metal complex dyestuffs
US3894841A (en) * 1972-03-07 1975-07-15 Hoechst Ag Process for the single-bath dyeing of unmodified polyolefin fibers with water-insoluble pigment dyestuffs
US3918897A (en) * 1972-03-07 1975-11-11 Hoechst Ag Process for the single-bath dyeing of unmodified polyolefin fibers with metal-containing phthalocyanine

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CH371088A (de) 1963-04-30
CH323361A4 (de) 1963-04-30
GB921975A (en) 1963-03-27

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