US3700405A - Dyeing of polycarbonamides of bis(paraamino-cyclohexyl)methane and dodecanediodic acid with anionic dyes - Google Patents

Dyeing of polycarbonamides of bis(paraamino-cyclohexyl)methane and dodecanediodic acid with anionic dyes Download PDF

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Publication number
US3700405A
US3700405A US102518A US3700405DA US3700405A US 3700405 A US3700405 A US 3700405A US 102518 A US102518 A US 102518A US 3700405D A US3700405D A US 3700405DA US 3700405 A US3700405 A US 3700405A
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United States
Prior art keywords
acid
dyeing
dyes
polycarbonamides
paraamino
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Expired - Lifetime
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US102518A
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English (en)
Inventor
Anthony M Petite
Clive E Thornley
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Novartis Corp
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Ciba Geigy Corp
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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02Material containing basic nitrogen
    • D06P3/04Material containing basic nitrogen containing amide groups
    • D06P3/24Polyamides; Polyurethanes
    • D06P3/241Polyamides; Polyurethanes using acid dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/44General 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
    • D06P1/64General 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 without sulfate or sulfonate groups
    • D06P1/651Compounds without nitrogen
    • D06P1/65106Oxygen-containing compounds
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92Synthetic fiber dyeing
    • Y10S8/924Polyamide fiber

Definitions

  • the present invention relates to processes for dyeing polyamide fibers containing at least 90% of the repeating units of the formula wherein R is the same or different member of the class consisting of hydrogen and methyl. At least 40% by weight of the diamino constituent of the repeating units is of the trans, trans stereoisomeric configuration.
  • these materials is the polyamide polycondensate of 4,4'- diamino-dicyclohexylmethane with dodecanedioic acid.
  • Such material is commercially avail able from Du Pont in different grades, depending on finish, denier, etc., as nylon types 472 and 473, as well as Qiana.
  • the latter materials have a silk-like handle, a density of 1.04 and a crystallinity similar to that of polyester fibers, as reported in an article entitled The Dyeing of Synthetic Polymer Fibers, A. Liddiard, appearing in Review of Progress in Coloration, vol. 1, p. 64, June l967-September 1969.
  • the Liddiard article does disclose that the Du Pont type 472 polyamides may be dyed with disperse dyes at the boil in the presence of a carrier, or in the absence of a carrier at even higher temperatures.
  • benzophenone With respect to carriers, the most preferred is benzophenone, however, this may be employed and mixed with other carriers such as butyl benzoate, especially in a 1:1 mixture.
  • Other operable carriers include benzyl benzoate, phenyl benzoate, o-bromo benzoic acid, 2-chloro benzoic acid, mono benzyl phthalate, o-anisaldehyde, benzoin, succinic acid and toluic acid.
  • Such carriers may be employed alone or in admixture with each other as well as with benzophenone and/or butyl benzoate. Normally, 10 to 25 weight percent of carrier, based on the weight of the fiber to be treated, produces satisfactory results.
  • temperatures of dyeing about 180 F. up to about the boiling point of the aqueous dyebath, e.g., about 212 F., may be employed with temperatures in the range of 200 to 212 F. being preferred.
  • Control of pH is very important and a pH range of between 2 and 5 must be employed to insure substantial dyebath exhaustion.
  • Conventional acids used in dyebath formulations e.g., formic, acetic, sulphuric or phosphoric acid are preferably employed.
  • Formic acid is most preferred because it offers the highest degree of exhaustion.
  • the dyestuffs falling within the scope of this invention are the anionic dyes.
  • Certain anionic dyes were found to be more satisfactory than others and among these are the direct dyes, e.g., Direct Red 81 (Cl. 28160), 2:1 premetallized azo dyes, e.g., Acid Red 201 (01. 18761) and Acid Red 180 (CL 8736) and azo or anthraquinone acid dyes.
  • the azo and anthraquinone acid dyes the most preferred are the monosulfonated ones.
  • the monosulfonated and monosulfonamides are most preferred.
  • Dyes such as monosulfonated azo Acid Yellow 29 (CI. 18900), monosulfonated azo Acid Red 4 (CI. 14710) and monosulfonated anthraquinone Acid Blue 27 (CI. 61530) gave excellent color yield and, in most cases, were totally exhausted after 60 minutes at 212 F.
  • dyes such as Acid Orange 45 (CI. 22195) Acid Red 73 (CI. 27290), Acid Blue 113 (CI. 26360) and Direct Yellow 44 (CI. 29000) gave poorer color yield and were far from total exhaustion.
  • the latter dyes all have more than one acidic groups, i.e. sulfonic or carboxylic acid group, however, by use of the carriers and conditions of the present invention, even these dyestuffs produced dyeings unattainable by the prior art.
  • anionic and nonionic wetting agents may be employed if desired.
  • Anionic wetting agents are preferred.
  • EXAMPLE 1 10 g. of Du Pont type 472 nylon fiber is immersed in a bath prepared as follows:
  • the fiber is immersed in the dyebath and the dyebath is heated at 2-3 F./min. to the boil, i.e., about 212 F.
  • the fiber is boiled for about one hour, washed with water and dried to achieve a deep, bright blue level dyeing. Fastness to wet and light conditions were outstanding.
  • EXAMPLE 2 Proceeding substantially in the same manner as in Example 1, several organic chemicals were employed to determine their carrier effect. Several were found to give significant exhaustion and these are benzyl benzoate, phenyl benzoate, o-bromobenzoic acid, 2-chlorobenzoic acid, monobenzyl phthalate, o-anisaldehyde, benzoin, succinic acid, and toluic acid.
  • R is the same or different member of the class consisting of hydrogen or methyl which comprises immersing said fiber in an aqueous dyebath containing (a) a carrier, benzophenone, in an amount effective to produce a level dyeing,
  • an anionic dyestulf selected from the group consisting of azo and anthraquinone acid dyestuffs, 2:1 premetallized azo dyestuffs and direct dyestuffs,
  • the pH of said dyebath being in the range of 2 to 5 and the temperature of said dyeing being from about F. to about 212 F.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
US102518A 1970-12-29 1970-12-29 Dyeing of polycarbonamides of bis(paraamino-cyclohexyl)methane and dodecanediodic acid with anionic dyes Expired - Lifetime US3700405A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US10251870A 1970-12-29 1970-12-29

Publications (1)

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US3700405A true US3700405A (en) 1972-10-24

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US102518A Expired - Lifetime US3700405A (en) 1970-12-29 1970-12-29 Dyeing of polycarbonamides of bis(paraamino-cyclohexyl)methane and dodecanediodic acid with anionic dyes

Country Status (9)

Country Link
US (1) US3700405A (nl)
BE (1) BE777360A (nl)
CA (1) CA970107A (nl)
CH (2) CH556941A (nl)
DE (1) DE2165165B2 (nl)
FR (1) FR2120052B1 (nl)
GB (1) GB1367178A (nl)
IT (1) IT945673B (nl)
NL (1) NL7117989A (nl)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4032291A (en) * 1976-01-12 1977-06-28 Ciba-Geigy Corporation Phenyl phthalate carriers in dyeing and printing synthetic fibers
US4221566A (en) * 1978-06-05 1980-09-09 Velsicol Chemical Corporation Dye compositions containing a combination of dye assistants which includes a mixture of lower alkyl esters of aromatic carboxylic acids
US4229178A (en) * 1978-06-05 1980-10-21 Velsicol Chemical Corporation Dye compositions
US4238191A (en) * 1979-11-26 1980-12-09 Burlington Industries, Inc. Bulking of polycarbonamides: qiana
US4308025A (en) * 1979-11-26 1981-12-29 Burlington Industries, Inc. Simultaneous bulking and dyeing process

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB943147A (en) * 1961-05-03 1963-11-27 British Nylon Spinners Ltd Improvements relating to the dyeing of high molecular weight polyamides
GB1096943A (en) * 1964-05-06 1967-12-29 Unilever Ltd Solvent assisted dyeing
US3510891A (en) * 1966-11-23 1970-05-12 Du Pont Dyeing polyamide fibers with pelargonic acid
DE1769997A1 (de) * 1968-08-20 1971-11-11 Hoechst Ag Verfahren zum Faerben von Wolle und Mischungen aus Wolle mit Polyesterfasern

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4032291A (en) * 1976-01-12 1977-06-28 Ciba-Geigy Corporation Phenyl phthalate carriers in dyeing and printing synthetic fibers
US4221566A (en) * 1978-06-05 1980-09-09 Velsicol Chemical Corporation Dye compositions containing a combination of dye assistants which includes a mixture of lower alkyl esters of aromatic carboxylic acids
US4229178A (en) * 1978-06-05 1980-10-21 Velsicol Chemical Corporation Dye compositions
US4238191A (en) * 1979-11-26 1980-12-09 Burlington Industries, Inc. Bulking of polycarbonamides: qiana
US4308025A (en) * 1979-11-26 1981-12-29 Burlington Industries, Inc. Simultaneous bulking and dyeing process

Also Published As

Publication number Publication date
DE2165165B2 (de) 1974-05-16
NL7117989A (nl) 1972-07-03
CH1843671A4 (nl) 1974-06-14
DE2165165C3 (nl) 1975-01-02
GB1367178A (en) 1974-09-18
FR2120052A1 (nl) 1972-08-11
BE777360A (fr) 1972-06-28
FR2120052B1 (nl) 1974-06-07
DE2165165A1 (de) 1972-07-06
CH556941A (nl) 1974-12-13
IT945673B (it) 1973-05-10
CA970107A (en) 1975-07-01

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