US3652199A - Process for drying polyamide fibers catonic dyes and zinc thiocyanate - Google Patents

Process for drying polyamide fibers catonic dyes and zinc thiocyanate Download PDF

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Publication number
US3652199A
US3652199A US853924A US3652199DA US3652199A US 3652199 A US3652199 A US 3652199A US 853924 A US853924 A US 853924A US 3652199D A US3652199D A US 3652199DA US 3652199 A US3652199 A US 3652199A
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United States
Prior art keywords
dye
bath
dyes
zinc thiocyanate
dyed
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US853924A
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English (en)
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Peter S K Leung
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EIDP Inc
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EI Du Pont de Nemours and Co
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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
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
    • C09B69/06—Dyestuff salts, e.g. salts of acid dyes with basic dyes of cationic dyes with organic acids or with inorganic complex acids
    • 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
    • D06P1/673—Inorganic compounds
    • D06P1/67333—Salts or hydroxides
    • D06P1/6735—Salts or hydroxides of alkaline or alkaline-earth metals with anions different from those provided for in D06P1/67341
    • D06P1/67375—Salts or hydroxides of alkaline or alkaline-earth metals with anions different from those provided for in D06P1/67341 with sulfur-containing anions
    • 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
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/24—Polyamides; Polyurethanes
    • D06P3/242—Polyamides; Polyurethanes 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
    • Y10S8/924—Polyamide fiber
    • Y10S8/925—Aromatic polyamide

Definitions

  • ABSTRACT Process for dyeing polyamide fibers with a cationic dye comprising treating said fibers with an aqueous bath containing a Q cationic dye and zinc thiocyanate at a temperature of at least 5 Claims, No Drawings PROCESS FOR DRYING POLYAMIDE FIBERS CATONIC DYES AND ZINC THIOCYANATE BACKGROUND OF THE INVENTION
  • This invention concerns a process for dyeing polyamide fibers with cationic dyes. These dyes are of particular interest for use in polyamides because of their bright shades, particularly in the red and pink colors and because of the fluorescence which some of the cationic dyes display.
  • Polyamide fibers have been the subject of much research in the field of dyeing, and numerous dyes are available, particularly in the disperse dye and acid dye categories.
  • the cationic dyes have been characterized by poor affinity and poor wash fasteners when applied to polyamide fibers. Fibers of polyamides containing aromatic or cyclohexane constituents are especially resistant to cationic dyes.
  • the present invention provides a process for dyeing polyamide fibers with a cationic dye comprising contacting said fibers with an aqueous bath containing a cationic dye and zinc thiocyanate at a temperature of at least 90 C., the amount of zinc thiocyanate in the bath being from 1 to 60 percent based on the weight of said fibers and less than 1.5 percent based on the weight of water in the bath.
  • This invention provides a process whereby cationic dyes can be applied to polyamide fibers in much the same manner as disperse dyes, i.e. by dissolving in the fiber and diffusing through it. The process is particularly useful for the polyamides containing aromatic constituents or cyclohexane constituents.
  • the polyamide fibers which may be dyed by the process of this invention include all of the commonly known polyamides such as poly(hexamethylene adipamide), the polymers obtained from f-caprolactam, and copolymers of these.
  • the process is particularly useful for application of cationic dyes to fibers of polyamides containing aromatic constituents, such as disclosed in US Pat. No. 3,063,966, and polyamides containing cyclohexane constituents, such as disclosed in US. Pat. No. 3,393,210.
  • the preferred polyamides are poly(metaphenylene isophthalamide) and the polymer derived from bis(4-aminocyclohexyl)-methane and dodecanedoic acid, i.e., poly(methylene-di-l ,4-cyclohexylene dodecane diamide).
  • the cationic dyes (sometimes known as basic dyes), in general, are chemical mixtures containing compounds with one or more onium groups such as the quaternary ammonium group.
  • the onium groups carry a positive charge; hence the name cationic.”
  • the principal constituent may also contain some anionic water-solubilizing groups such as sulfonic or carboxylic acid groups provided that there are more equivalents of the cationic groups then of the anionic groups.
  • suitable cationic dyes is disclosed in Canadian Pat. No. 794,953.
  • Other useful cationic dyes are disclosed in US. Pat. No. 3,338,660.
  • the aqueous dye bath used in this invention must contain zinc thiocyanate which promotes high color yield and high wash fastness without affecting appreciably the physical properties of the fiber.
  • the color yield for cationic dyes applied to polyamide fibers in the presence of zinc thiocyanate is usually at least 2.5 times as great as the color yield without zinc thiocyanate.
  • the color yield of the dyed fibrous polyamides is measured by the K/S value (Kubelka-Munk absorption-scattering factor) which is calculated from the expression K/S i lR) /2R where R is the fraction of light reflected at maximum absorption wavelength from the dyed yarn or fabric.
  • the K/S value for dyeing in the presence of the anionic agent is divided by the K/S value obtained in the absence of the anionic agent and multiplied by 100.
  • the dye bath may contain zinc thiocyanate or its equivalent ionic components. It should be understood that the zinc cations, thiocyanate anions, or thiocyanate complex ions may be supplied from separate chemicals. It is only essential that the zinc cation and thiocyanate anion be available in sufficient quantity to give 1 to 60 percent of the equivalent zinc thiocyanate based on the weight of the fibers and less than 1.5 percent by weight based on weight of water in the bath.
  • dye carriers are useful in dyeing poly(meta-phenylene isophthalamide) fibers and poly-(methylene-di-l ,4- cyclohexylene dodecane diamide) fibers.
  • Suitable dye carriers for these two types of fibers include butyl benzoate, pelargonic acid, mixtures of benzanilide and dirnethyl terephthalate, o-phenyl phenol, chlorinated benzene, biphenyl, and methyl salicylate.
  • the temperature of the aqueous dye bath is at least 194F. (C.), but usually less than about 270F. (132C). Obviously, adequate pressure equipment must be provided for dyeing in aqueous baths at temperatures above 212F. (C).
  • the aqueous dye bath preferably is acidic.
  • Conventional dye bath additives also may be used, if desired, such as surface active agents and leveling agents.
  • Citric acid is a particularly desirable leveling agent.
  • poly(metaphenylene isophthalamide) is abbreviated MPD-I and poly- (methylene-di-l,4-cyclohexylene dodecane diamide) is abbreviated PACM-l2.
  • all percentages are on a weight basis.
  • EXAMPLE I EFFECT OF ZINC TI-IIOCYANATE CONCENTRATION ON COLOR VALUE FOR MPD-I SAMPLES
  • Ten swatches of fabric woven from MPD-l fibers weighing 10 g. each are introduced into 10 separate aqueous baths at 100F. (38C.).
  • Each bath contains 0.1 G. Merpol HCS (a nonionic surfactant), 1.5 gm.
  • Latyl Carrier A a mixture of benzanilide and dimethyl terephthalate
  • 4 g. glacial acetic acid 0.3 g.
  • Calcozine Acrylic Blue H? (a cationic dye, Color Index Basic Blue 54).
  • Each bath contains a different amount of zinc thiocyanate as indicated in Table l.
  • the baths containing the fabric samples are heated to 250F. (121C.) and kept at this temperature for 2 hours. After this the samples are removed from the baths and rinsed. Then the dyed samples are scoured for 30 minutes in 400 ml. of aqueous bath containing 0.1 g. Merpol HCS (nonionic surfactant) and 0.1 g. tetrasodium pyrophosphate at a temperature of 200F. (93C.). The dyed and scoured material is then rinsed and dried. A series of blue dyed fabric samples are obtained which have good wash fastness. The color yield for each of the dyeings is indicated in Table'l.
  • the dyed swatches are then removed from the dye bath and rinsed. Then they are scoured for 30 minutes at 180F. (82C.) in 200 ml. aqueous baths containing 0.05 g. Merpol HCS and 0.05 g. tetrasodium pyrophosphate. The swatches are then rinsed and dried. A se- 40 ries of yellow, red, and blue dyeings are obtained which have good wash fastness.
  • the carriers were added in sufficient quantity to give 15 percent by weight, based on fiber.
  • the 10 baths each containing a different carrier or no carrier were heated to 250F. 121C.) and kept at this temperature for 2 hours.
  • the dyed materials were then removed from each of the dye baths and rinsed.
  • the dyed materials were scoured for 30 minutes in 400 ml. of another aqueous bath containing 0.1 g. Merpol l-lCS and 0.1 g. tetrasodium pyrophosphate at a temperature of 200"F. (93C.).
  • the dyed and scoured materials were then rinsed and dried. A series of blue dyeings is obtained which have good wash fastness.
  • EXAMPLE IV Swatches (5 g.) of PACM-IZ wovenfabric are introduced into 51 separate aqueous baths at F. (38C.). Each of the baths contains 200 ml. of water, 4 g. citric acid, 0.05 g. Merpol I-ICS, 2 g. zinc thiocyanate (1 percent based on water, 40 percent based on fiber), and 0.75 g. of one of the dye carriers shown in Table 4. In addition, one of the three dyes shown in Table 4 is added. In each case the amount of dye is 0.1 g. The bath is then heated to 212F. (100C.) and kept at this temperature for 90 minutes. The dyed fabric samples are then removed from the dye baths and rinsed.
  • the dyed samples are scoured for 30 minutes at 180F. (82C.) in 200 ml. of another aqueous bath containing 0.05 g. Merpo1" HCS and 0.05 g. tetrasodium pyrophosphate.
  • the dyed and scoured materials are then rinsed and dried. A series of orange, red and blue dyeings are obtained which have good wash fastness.
  • EXAMPLE V EFFECT OF TEMPERATURE ON DYEING OF MPD-l Swatches of MPD-l woven fabric, each weighing 10 g. are introduced into twelve 400 ml. aqueous baths each containing 0.3 g. of one of the dyes indicated in Table 5. Each of the baths also contains 0.1 g. Merpol HCS, 1.0 g. zinc thiocyanate (0.25 percent based on weight of water, 10 percent based on weight of fiber), 3.5 g. of Latyl" Carrier A and 4.0 g. glacial acetic acid. The dye baths are heated to the temperatures indicated in Table and maintained at this temperature for 2 hours.
  • Identical dyeings are performed at 212F., 230F., 250F., and 270F. (100C, 110C.', 121C., and 132C, respectively).
  • the dyed material is then removed from the baths and rinsed.
  • the dyed material is scoured for 30 minutes at 200F. (93C.) in 400 ml. of another aqueous bath containing 0.1 g. Merpol l-lCS and 0.1 g. tetrasodium pyrophosphate.
  • the dyed and scoured materials are then rinsed and dried. A series of yellow, red, and blue dyed fabrics is obtained, each having good wet fastness.
  • EXAMPLE VI DYEING OF MIXED FILAMENT YARN A mixed filament yam of 60 denier containing 18 filaments of PACM-12 and 18 filaments of a copolymer derived from bis(4-aminocyclohexyl)methane and a mixture of diacids composed of 90 mole percent dodecanedioic acid and mole percent isophthalic acid is prepared for dyeing in a package dyer. Twenty-four ia-lb. packages are prepared using yarns having 5 turns/inch (2 tums/cm.) Z twist. The yarns are first packaged on collapsible mufis and are then preshrunk by treatment in a steam autoclave at 127C. for 30 min.
  • the yarn from the muff is then rewound onto 24 perforated steel cylinders.
  • the cylinders are then loaded into a 48 gallon kier with a 5 gallon expansion tank. All subsequent steps, e.g. scouring, dyeing, etc., are conducted at maximum capacity of the kier.
  • the bath:fiber weight ratio if 35:1 for a 12 1b. yarn load.
  • Direction of liquor flow in the kier is changed every three minutes.
  • the preshrunk yarn is scoured with 54.5 g. each of Merpol HCS and tetrasodiurn pyrophosphate for 20 minutes at 1 F. (82C.) to remove finishes or oils applied during earlier processing.
  • the dyed yarn then is scoured with 54.5 g. each of Merpol I-lCS and tetrasodium pyrophosphate for 20 min. at 140F. (60C.) to remove surface dye.
  • the dyed yarns finally are removed from the kier and dried with hot compressed air.
  • Zinc thiocyanate is shown to be far superior to the other salts, including other thiocyanates, in promoting dyeability of the polyarnide fabric with a cationic dye.
  • V the amount of zinc thiocyanate in the bath being from 1 to percent based on the weight of said fibers and less than 1.5 percent based on the weight of water in the bath.
  • polyamide is poly(methylene-di-l ,4cyclohexylene dodecane diamide).

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  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Organic Chemistry (AREA)
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US853924A 1969-08-28 1969-08-28 Process for drying polyamide fibers catonic dyes and zinc thiocyanate Expired - Lifetime US3652199A (en)

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BE (1) BE754714A (fr)
DE (1) DE2042858A1 (fr)
FR (1) FR2059720A1 (fr)
NL (1) NL7012653A (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0228043A3 (fr) * 1985-12-28 1990-06-06 Hoechst Aktiengesellschaft Sels colorants, leur procédé de fabrication et leur utilisation
US5110317A (en) * 1987-09-28 1992-05-05 Allied-Signal Inc. Methods and compositions to enhance stain resistance of dyed nylon carpet fibers: thiocyanate to reduce yellowing
US5145487A (en) * 1987-09-28 1992-09-08 Allied-Signal Inc. Methods and compositions to enhance stain resistance of carpet fibers using sulfonated aromatic condensates
US5152803A (en) * 1987-09-28 1992-10-06 Allied-Signal Inc. Methods and compositions to enhance stain resistance of carpet fibers with water-soluble thiocyanate
US5230708A (en) * 1987-09-28 1993-07-27 Allied-Signal Inc. Methods and compositions to enhance stain resistance of nylon carpet fibers: thlocyanate to reduce yellowing
US5298201A (en) * 1990-12-21 1994-03-29 Milliken Research Corporation Method for improving dyeability of fiber and associated fabric utilizing radiation
US5404625A (en) * 1990-10-12 1995-04-11 Milliken Research Corporation Method and apparatus for modifying fibers and fabric by impaction with particles
US5487856A (en) * 1993-08-16 1996-01-30 Basf Corporation Process for the manufacture of a post-heat set dyed fabric of polyamide fibers having improved dye washfastness and heat stability
US6258928B1 (en) 2000-04-06 2001-07-10 E. I. Du Pont De Nemours And Company Process for improving characteristics of a polyamide

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB603154A (en) * 1944-01-10 1948-06-10 Durand & Huguenin Ag Process for improving the fastness to light of dyeings or prints produced with vat dyestuffs or leuco ester salts thereof on fibres, fabrics, films and like-shaped structures composed of superpolyamides or superpolyurethanes
GB642840A (en) * 1948-02-26 1950-09-13 Henry Charles Olpin Improvements in coloured textile materials
GB813289A (en) * 1955-09-26 1959-05-13 Heberlein & Co Ag Improvements in or relating to the treatment of textile fabrics
US3063966A (en) * 1958-02-05 1962-11-13 Du Pont Process of making wholly aromatic polyamides
US3338660A (en) * 1963-04-24 1967-08-29 Geigy Ag J R Process for producing fast dyeings on polyamide fiber material
US3349062A (en) * 1966-07-21 1967-10-24 Du Pont Halogenated aromatic polyamides
CA794753A (en) * 1968-09-17 C. Cobb Malcolm Dyed textile materials
US3506990A (en) * 1966-12-16 1970-04-21 Du Pont Process for dyeing drawn filaments of aromatic polyamides with basic dye-stuffs in the presence of an organic dye carrier

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA794753A (en) * 1968-09-17 C. Cobb Malcolm Dyed textile materials
GB603154A (en) * 1944-01-10 1948-06-10 Durand & Huguenin Ag Process for improving the fastness to light of dyeings or prints produced with vat dyestuffs or leuco ester salts thereof on fibres, fabrics, films and like-shaped structures composed of superpolyamides or superpolyurethanes
GB642840A (en) * 1948-02-26 1950-09-13 Henry Charles Olpin Improvements in coloured textile materials
GB813289A (en) * 1955-09-26 1959-05-13 Heberlein & Co Ag Improvements in or relating to the treatment of textile fabrics
US3063966A (en) * 1958-02-05 1962-11-13 Du Pont Process of making wholly aromatic polyamides
US3338660A (en) * 1963-04-24 1967-08-29 Geigy Ag J R Process for producing fast dyeings on polyamide fiber material
US3349062A (en) * 1966-07-21 1967-10-24 Du Pont Halogenated aromatic polyamides
US3506990A (en) * 1966-12-16 1970-04-21 Du Pont Process for dyeing drawn filaments of aromatic polyamides with basic dye-stuffs in the presence of an organic dye carrier

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
R. W. Schumm et al., (A publication by AATCC), Aug. 27, 1969, Vol. 1, No. 18, pages 27 30 *

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0228043A3 (fr) * 1985-12-28 1990-06-06 Hoechst Aktiengesellschaft Sels colorants, leur procédé de fabrication et leur utilisation
US5110317A (en) * 1987-09-28 1992-05-05 Allied-Signal Inc. Methods and compositions to enhance stain resistance of dyed nylon carpet fibers: thiocyanate to reduce yellowing
US5145487A (en) * 1987-09-28 1992-09-08 Allied-Signal Inc. Methods and compositions to enhance stain resistance of carpet fibers using sulfonated aromatic condensates
US5152803A (en) * 1987-09-28 1992-10-06 Allied-Signal Inc. Methods and compositions to enhance stain resistance of carpet fibers with water-soluble thiocyanate
US5230708A (en) * 1987-09-28 1993-07-27 Allied-Signal Inc. Methods and compositions to enhance stain resistance of nylon carpet fibers: thlocyanate to reduce yellowing
US5404625A (en) * 1990-10-12 1995-04-11 Milliken Research Corporation Method and apparatus for modifying fibers and fabric by impaction with particles
US5298201A (en) * 1990-12-21 1994-03-29 Milliken Research Corporation Method for improving dyeability of fiber and associated fabric utilizing radiation
US5487856A (en) * 1993-08-16 1996-01-30 Basf Corporation Process for the manufacture of a post-heat set dyed fabric of polyamide fibers having improved dye washfastness and heat stability
US6258928B1 (en) 2000-04-06 2001-07-10 E. I. Du Pont De Nemours And Company Process for improving characteristics of a polyamide
WO2001077207A3 (fr) * 2000-04-06 2002-02-28 Du Pont Procede d"amelioration des caracteristiques d"une polyamide
AU2001251038B2 (en) * 2000-04-06 2004-11-25 Invista Technologies S.A.R.L. Process for improving characteristics of a polyamide

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Publication number Publication date
DE2042858A1 (de) 1971-03-11
BE754714A (fr) 1971-01-18
NL7012653A (fr) 1971-03-02
FR2059720A1 (fr) 1971-06-04

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