US3844712A - Treatment of dyed polyamides - Google Patents

Treatment of dyed polyamides Download PDF

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Publication number
US3844712A
US3844712A US00796545A US79654569A US3844712A US 3844712 A US3844712 A US 3844712A US 00796545 A US00796545 A US 00796545A US 79654569 A US79654569 A US 79654569A US 3844712 A US3844712 A US 3844712A
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US
United States
Prior art keywords
dyed
treatment
fastness
wet fastness
polyamides
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
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US00796545A
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English (en)
Inventor
G Frickenhaus
H Otten
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Bayer AG
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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 US3844712A publication Critical patent/US3844712A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/02—After-treatment
    • D06P5/04—After-treatment with organic 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
    • 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
    • D06P1/62—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 using compositions containing low-molecular-weight organic compounds with sulfate, sulfonate, sulfenic or sulfinic groups
    • D06P1/621—Compounds without nitrogen
    • D06P1/622—Sulfonic acids or their salts
    • D06P1/625—Aromatic

Definitions

  • an object of this invention to provide a method of treating cationically dyed polyamide materials to improve the wet fastness of such materials.
  • Another object is to improve such wet fastness without impairing rubbing fastness or brightness of the cationically dyed polyamides.
  • Still another object is to improve the wet fastness of cationic component of bi-color dyeings without impairing the wet fastness of the anionic component.
  • a further object of the invention is to provide compounds for improving the wet fastness f cationically dyed polyamide materials.
  • R signifies a lower alkyl radical having l-4 carbon atoms
  • the process of applying these compounds comprises treating the dyeings produced with cationic dyes on synthetic polyamide with aqueous liquors, which contain alkali or ammonium salts of condensation products of formaldehyde and the aromatic sulfonic acids of formula (1).
  • the aromatic sulfonic acids adapted for use in this invention as defined by formula (1) are particularly those containing as diaryl ethers (A) components such as diphenyl ether and 4.4'-dimethvl-dinhenv1 ether. Sulfonation of these diaryl ether nuclei can be conducted by reaction with sulfonating agents such as sulfuric acid monohydrate or chlorosulfonic acid under the conditions specified in US. Pat. No. 2,315,951. The degree of sulfonation can vary as taught in said patent, but the desired aromatic sulfonic acids should contain from V2 to 2 sulfonic acid groups in a position on the aryl nuclei. The sulfonating agent should be present in quantities of about 0.6 to 2.5 mols per mol of diaryl ether.
  • the sulfonated diaryl ethers may then be condensed with formaldehyde from any suitable source by reactcondensation or condensation followed by sulfonation.
  • the sulfonic acid salts can be formed by conventional techniques for reacting sulfonic acids with ammonium or alkali metal salts.
  • Particularly suitable bases adapted to yield ammonium or alkali metal salts of the sulfonic acids are ammonia, methylamine, cyclohexylamine, mono-, dior triethanolamine and alkali hydroxides such as sodium or potassium hydroxide.
  • the salt of the condensation product After the salt of the condensation product is formed, it can be applied to dyed synthetic polyamide textile materials in such forms as threads, fibers, fibrous or knitted goods, particularly where the synthetic polyamide is an anionically modified synthetic polyamide, e.g., anionically modified e-polycaprolactam, polyhexamethylene diamine adipate or poly-1 l-aminoundecanic acid.
  • anionically modified synthetic polyamide e.g., anionically modified e-polycaprolactam, polyhexamethylene diamine adipate or poly-1 l-aminoundecanic acid.
  • These synthetic polyamide textiles can be previously dyed with any cationic dyestuff including classes of dyes such as the diphenylmethane, triphenylmethane, rhodamine, thiazine, oxazine, methine, azomethine dyes as are described, e.g., in American Dyestuff Reporter (1954), pages 432 433, and particularly anthraquinone dyes and azo dyestuffs with a basic or quaternary amino group as described in British Pat. Nos. 785,988; 871,624; 791,932; 930,471; and
  • the pH is adjusted by adding organic acids such as formic acid.
  • the goods While in the solution, the goods should be slightly agitated as by moving for a period of about 10-60 minutes while the solution is maintained at a temperature of about 30-100C, preferably 4070C.
  • EXAMPLE 1 la Threads formed from anionically modified polyhexamethylene diamine adipate, were dyed with 1 percent by weight of a cationic dyestuff corresponding to the formula:
  • TREATED THREADS CON- TROL Washing fastness 3 (determined according to ISO/R lO5/lV-l968. Part 10): 5 (4-5) Fastness to water b (determined according to ISO/R l05/l-l959. Part 22): 4-5 (3) Fastness to perspiration acid (determined according to ISO/R l05/lV-l968, Part 4): 4 (2-3) Fastness to perspiration alkaline (determined 2 according to lSO/R l05/lV-l968, Part 4): 3-4
  • Example 1 0.35 g 85 percent acid and 0.75 g condensation product of Example 1.
  • the liquor contained 2.5 percent of the condensation product based on the weight of the hanks. Subsequently, the hanks were rinsed in fresh water and dried.
  • the hank which was anionically modified shows considerable improvement in fastness to water, washing, and perspiration, whereas the fastness properties of the dyed unmodified material remain uneffected.
  • the properties of the anionic dye component are thus not impaired by the after-treatment of this invention.
  • A signifies diphenyl ether radical
  • R signifies an alkyl radical containing l-4 carbon atoms
  • m a whole number from 0-2
  • n a number from 0.5-2.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
US00796545A 1968-06-15 1969-02-04 Treatment of dyed polyamides Expired - Lifetime US3844712A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19681769613 DE1769613A1 (de) 1968-06-15 1968-06-15 Mittel zur Verbesserung der Nassechtheiten von mit kationischen Farbstoffen auf synthetischen Polyamiden erzeugten Faerbungen

Publications (1)

Publication Number Publication Date
US3844712A true US3844712A (en) 1974-10-29

Family

ID=5700207

Family Applications (1)

Application Number Title Priority Date Filing Date
US00796545A Expired - Lifetime US3844712A (en) 1968-06-15 1969-02-04 Treatment of dyed polyamides

Country Status (7)

Country Link
US (1) US3844712A (enrdf_load_stackoverflow)
AT (1) AT298399B (enrdf_load_stackoverflow)
BE (1) BE734522A (enrdf_load_stackoverflow)
DE (1) DE1769613A1 (enrdf_load_stackoverflow)
FR (1) FR2010968A1 (enrdf_load_stackoverflow)
GB (1) GB1258012A (enrdf_load_stackoverflow)
NL (1) NL6909055A (enrdf_load_stackoverflow)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3936268A (en) * 1974-11-07 1976-02-03 Diamond Shamrock Corporation Method of reducing barre in synthetic polymide textiles dyed with acid dyes
US4295852A (en) * 1979-11-08 1981-10-20 Bayer Aktiengesellschaft Process for dyeing polyamide fibres
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
US5190565A (en) * 1986-07-28 1993-03-02 Allied-Signal Inc. Sulfonated 2-(2'-hydroxyaryl)-2H-benzotriazoles and/or sulfonated aromatic formaldehyde condensates and their use to improve stain resistance and dye lightfasteness
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
US6846336B1 (en) * 1999-11-10 2005-01-25 Bayer Aktiengesellschaft Acid-resistant solutions containing aromatic formaldehyde condensation products
US20060248655A1 (en) * 2003-03-14 2006-11-09 Lambert James D Stainblocker polymers
CN108396564A (zh) * 2018-03-16 2018-08-14 郑州鸿盛数码科技股份有限公司 一种分散型阳离子染料水性色浆及其制备方法

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2315951A (en) * 1941-04-25 1943-04-06 Du Pont Condensation products of diaryl ether sulphonic acids with formaldehyde
US2716655A (en) * 1954-01-12 1955-08-30 Du Pont Dyes and dye intermediates of the anthraquinone series
GB807241A (en) * 1955-08-30 1959-01-14 Bayer Ag Anthraquinone dyestuffs
US2922690A (en) * 1956-04-18 1960-01-26 Basf Ag Dyestuffs for dyeing and printing fibre mixtures which contain fibres containing acrylonitrile
US2972508A (en) * 1955-12-29 1961-02-21 Bayer Ag Dyeing of polymers of acrylonitrile
CA699533A (en) * 1964-12-08 J. I. Harding Arthur Dyeing multifilament nylon
GB1092247A (en) * 1964-09-18 1967-11-22 Shell Int Research An apparatus for supporting an element from a floating marine platform
US3389549A (en) * 1966-01-17 1968-06-25 Du Pont Aromatic dicarbonyl sulfonate modified polycarbonamides
US3475111A (en) * 1964-07-14 1969-10-28 Glanzstoff Ag Tone-on-tone acid dyeing blended textile of nylon and nylons with small amounts of phthalic acid sulfonic acid,phosphoric or phosphonic acid ester condensed therein and the textile so produced
US3504997A (en) * 1963-12-17 1970-04-07 Du Pont Process for dyeing and printing anionic polymeric fibers

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA699533A (en) * 1964-12-08 J. I. Harding Arthur Dyeing multifilament nylon
US2315951A (en) * 1941-04-25 1943-04-06 Du Pont Condensation products of diaryl ether sulphonic acids with formaldehyde
US2716655A (en) * 1954-01-12 1955-08-30 Du Pont Dyes and dye intermediates of the anthraquinone series
GB807241A (en) * 1955-08-30 1959-01-14 Bayer Ag Anthraquinone dyestuffs
US2972508A (en) * 1955-12-29 1961-02-21 Bayer Ag Dyeing of polymers of acrylonitrile
US2922690A (en) * 1956-04-18 1960-01-26 Basf Ag Dyestuffs for dyeing and printing fibre mixtures which contain fibres containing acrylonitrile
US3504997A (en) * 1963-12-17 1970-04-07 Du Pont Process for dyeing and printing anionic polymeric fibers
US3475111A (en) * 1964-07-14 1969-10-28 Glanzstoff Ag Tone-on-tone acid dyeing blended textile of nylon and nylons with small amounts of phthalic acid sulfonic acid,phosphoric or phosphonic acid ester condensed therein and the textile so produced
GB1092247A (en) * 1964-09-18 1967-11-22 Shell Int Research An apparatus for supporting an element from a floating marine platform
US3389549A (en) * 1966-01-17 1968-06-25 Du Pont Aromatic dicarbonyl sulfonate modified polycarbonamides

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
American Dyestuff Reporter, Sept. 25, 1967, pages 749 and 750. *
Egli, Chem. Abst. 139,597, 1968. *
Egli, Textilveredlung Vol. 2; No. 11, pages 856 864, 1967. *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3936268A (en) * 1974-11-07 1976-02-03 Diamond Shamrock Corporation Method of reducing barre in synthetic polymide textiles dyed with acid dyes
US4295852A (en) * 1979-11-08 1981-10-20 Bayer Aktiengesellschaft Process for dyeing polyamide fibres
US5190565A (en) * 1986-07-28 1993-03-02 Allied-Signal Inc. Sulfonated 2-(2'-hydroxyaryl)-2H-benzotriazoles and/or sulfonated aromatic formaldehyde condensates and their use to improve stain resistance and dye lightfasteness
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
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
US6846336B1 (en) * 1999-11-10 2005-01-25 Bayer Aktiengesellschaft Acid-resistant solutions containing aromatic formaldehyde condensation products
US20060248655A1 (en) * 2003-03-14 2006-11-09 Lambert James D Stainblocker polymers
CN108396564A (zh) * 2018-03-16 2018-08-14 郑州鸿盛数码科技股份有限公司 一种分散型阳离子染料水性色浆及其制备方法

Also Published As

Publication number Publication date
GB1258012A (enrdf_load_stackoverflow) 1971-12-22
FR2010968A1 (fr) 1970-02-20
DE1769613A1 (de) 1971-07-01
BE734522A (enrdf_load_stackoverflow) 1969-11-17
NL6909055A (enrdf_load_stackoverflow) 1969-12-17
AT298399B (de) 1972-04-15

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