US3627473A - Process for dyeing nylon in pink shades - Google Patents

Process for dyeing nylon in pink shades Download PDF

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Publication number
US3627473A
US3627473A US452848A US3627473DA US3627473A US 3627473 A US3627473 A US 3627473A US 452848 A US452848 A US 452848A US 3627473D A US3627473D A US 3627473DA US 3627473 A US3627473 A US 3627473A
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US
United States
Prior art keywords
dye
grams
dyeing
nylon
fibers
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Expired - Lifetime
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US452848A
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English (en)
Inventor
Robert W Eltonhead
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Crompton and Knowles Corp
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Crompton and Knowles Corp
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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
    • 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
    • D06P3/241—Polyamides; Polyurethanes using acid dyes
    • 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
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
    • C09B1/503—Amino-hydroxy-anthraquinones; Ethers and esters thereof unsubstituted amino-hydroxy anthraquinone
    • 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
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
    • C09B1/54—Amino-hydroxy-anthraquinones; Ethers and esters thereof etherified
    • C09B1/547—Anthraquinones with aromatic ether groups
    • 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
    • Y10S8/916—Natural fiber dyeing
    • Y10S8/917—Wool or silk
    • 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

Definitions

  • a dyes for use in the process of this invention are obtained by sulfonating known l-amino-2- phenoxy-4-hydroxy anthraquinones having an unsubstituted phenoxy ring or C to C alkyl substituents in the phenoxy ring that provide the desired R substitution under conditions that will introduce a single sulfonic group in the dye molecule.
  • the unsulfonated anthraquinone precursors of the Structure A dyes have been reported as being useful as dispersed dyes for synthetic fibers. When applied as dispersed dyes they impart red shades toacetate, triacetate, modacrylic, polyester and nylon fibers and they merely stain without dyeing cotton, acrylic, silk and wool fibers.
  • the Structure A dyes have different, unique and unexpected properties as compared to their unsulfonated precursors. They are acid dyes for natural and synthetic polyamide fibers such as silk, wool and nylon. They do not dye and exhibit good reserving properties with re- 3,627,473 Patented Dec. 14, 1971 ice spect to acetate, triacetate, acrylic, modacrylic and polyester fibers.
  • the Structure A dyes impart to the polyamide fibers bright, bluish red shades having a high degree of lightfastness. Further, and in contrast to their unsulfonated anthraquinone precursors, the Structure A dyes will produce superior washfastness for a given depth of shade and their sublimation fastness is also superior. After treatments with conventional fixatives or fastening agents such as tannic acid-tartar emetic, so-called back tanning agents or syntans, etc. greatly enhance the washfastness of dyeings produced using the Structure A dyes, whereas such after treatments have little or no effect on the washfastness of dyeings made with the unsulfonated precursor applied as a dispersed dye.
  • fixatives or fastening agents such as tannic acid-tartar emetic, so-called back tanning agents or syntans, etc.
  • Structure A dyes in which the R substituent is an alkyl radical having from 5 to 9 carbons because they will dye nylon from neutral solution with a very high degree of exhaustion and thereby minimize the danger of fiber degradation that can occur when dyes must be applied from hot strongly acid dye baths.
  • the R group contains less than 5 carbons, the neutral dyeing capabilities will be lowered. Further, if the R group contains more than 9 carbons, and as the number of carbons in the R group increases over 9, the neutral dyeing capabilities will become increasingly impaired.
  • the sulfonation of the anthraquinone precursor is carried out in a conventional manner under a variety of acid strength, times and temperatures so as to introduce a sulfonic group into the dye molecule.
  • the exact positioning of the sulfonic group on the phenoxy ring is not known and it could be in either of the ortho or meta posi tions or it could even consist of a mixture of the ortho and meta substituted s-ulfonics.
  • the anthraquinone precursor and the oleum are reacted in quantities that only an average of one sulfonic group is introduced in the dye.
  • the completion of sulfonation may be determined by testing the solubility of a drop of the sulfonation reaction mass in hot water. When sulfonation is complete, no insoluble starting material will be observed.
  • the fibers are maintained in contact with the neutral dye liquor for a sufiicient time to exhaust dye onto the fiber.
  • the neutral dye liquor for a sufiicient time to exhaust dye onto the fiber.
  • the fibers With most of the Structure A dyes a substantial portion of the dye will exhaust onto the fiber from the neutral (pH 6.5 to 7.5) dye bath within about thirty minutes at temperatures of about 200 F.
  • To fully exhaust the dye onto the fiber it is necessary to lower the pH of the bath to render it mildly acid.
  • substantially complete exhaustion can be obtained if the pH of the bath is lowered to about 6, and for other Structure A dyes substantially complete exhaustion is obtained when the pH is lowered to about 3.5; in both cases the fiber being maintained at elevated temperatures of about 200 F. for an additional time of about 30 minutes.
  • EXAMPLE 1 144 grams of octyl phenol, 11.8 grams of potassium carbonate, calcined and 20.4 grams of 1 amino 2 bromo 4 hydroxy anthraquinone were heated with stirring to C. and held at 150 C. for 5 hours. After cooling, methanol was added and the slurry (500 ml. vol.) was filtered. The filter cake was washed with methanol, then water, then dried. Obtained 18.8 grams of 1 amino 2 octylphenoxy 4 hydroxy anthraquinone. 10 grams of this was sulfonated by adding it over 30 minutes with stirring to 79 ml. of 25% oleum while holding the temperature under 20 C. by means of a cooling bath.
  • EXAMPLE 4 130 grams of para tert. butyl phenol, 11.8 grams of anhydrous potassium carbonate and 25 grams of 1 amino 2 bromo 4 hydroxy anthraquinone were heated with stirring to 150 C. and held at that temperature for 6 hours. After cooling, 300 ml. of methanol were added and the slurry was filtered. After washing with methanol followed by water the filter cake was dried. Obtained 23.5 grams of 1 amino 2 para tert. butylphenoxy 4 hydroxy anthraquinone. 10 grams of this was sulfonated by adding it to 150 grams of 25 oleum over 10 minutes while holding the temperature at 17-19 C., by means of a cooling bath.
  • EXAMPLE 6- .5 gram of dyestuff from Example 2 (sulfonated 1 amino 2-p-amylphenoxy 4 hydroxy anthraquinone sodium salt) was dissolved in boiling soft water following which the volume for the dye solution was adjusted to 500 ml. with additional soft water. 5 ml. of this solution was then placed in each of four 400 ml. dye beakers and the solution in each beaker was made up to 250 ml. with soft water. The dye bath solutions had a pH of 8.4 at 22 C.
  • the nylon, silk and wool bands on the multifiber were dyed red, whereas the polyester was only slightly stained.
  • the nylon tricot pieces were all dyed about the same depth of shade.
  • the baths to which monosodium phosphate and acetic acid dye had been added showed complete exhaustion of color. In the neutral dyebath only a trace of color remained.
  • EXAMPLE 7 .2 gram of dyestuff from Example 2 was added to 1200 ml. of soft water which was heated to a boil to effect solution. The dye solution was cooled to 160 F. and four 5 gram pieces of nylon 66 tricot dull were introduced. While the fabric was stirred in the dyebath, the temperature of the dyebath was raised to ZOO-210 F. and held for one hour, following which the fabric pieces were rinsed and dried. The nylon was dyed a bright bluish red.
  • EXAMPLE 8 2 gram of unsulfonated dyestuff (l-amino-Z-para tert. amylphenoxy-4-hydroxy anthraquinone) used in preparing the dye in Example 2 is dissolved in 20 ml. of acetone. The solution was added to a solution of 2 grams of Lignin sulfonate dissolved in 1200 ml. of soft water contained in a dye beaker and the acetone removed by boiling. Four 5 grams pieces of nylon tricot were introduced. While the fabric was stirred in the dyebath, the temperature was held at ZOO-210 F. for one hour following which the fabric pieces were rinsed and dried. The nylon was dyed a dull bluish red.
  • a piece of dyed fabric from Example 7 was introduced into one set of each solution and a piece of dyed fabric from Example 8 'was introduced into the other set of solutions.
  • the method of dyeing natural and synthetic polyamide fibers which comprises entering the fibers into a substantially neutral aqueous dye bath at about room temperature, said bath containing a dye having the structure-- wherein R represents a substituent selected from the group consisting of H and alkyl groups having from 1 to 9 carbons; raising the temperature of the bath to about 200 F., maintaining the fiber in contact with the dye liquor for a sufficient time to exhaust dye onto the fiber, lowering the pH of the bath to render it mildly acid maintaining the fiber and acidified dye liquor in contact for a sufficient time to substantially completely exhaust the dye from the bath onto the fiber, and then removing the fibers from the bath.
  • a dye having the structure-- wherein R represents a substituent selected from the group consisting of H and alkyl groups having from 1 to 9 carbons raising the temperature of the bath to about 200 F., maintaining the fiber in contact with the dye liquor for a sufficient time to exhaust dye onto the fiber, lowering the pH of the bath to render it mildly acid maintaining the fiber and acidified dye liquor in contact
  • R is an alkyl group having from five to nine carbons.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
US452848A 1965-05-03 1965-05-03 Process for dyeing nylon in pink shades Expired - Lifetime US3627473A (en)

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US (1) US3627473A (forum.php)
JP (1) JPS516265B1 (forum.php)
CH (1) CH469859A (forum.php)
DE (1) DE1619381A1 (forum.php)
FR (1) FR1478768A (forum.php)
GB (1) GB1141156A (forum.php)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4350494A (en) * 1976-01-06 1982-09-21 Ciba-Geigy Corporation Process for the dyeing of textile material and apparatus for carrying out the process
US6028046A (en) * 1997-08-11 2000-02-22 Witco Corporation Detergents with polyamine alkoxylates useful in cleaning dyed fabrics while inhibiting dye transfer
CN104448886A (zh) * 2014-11-24 2015-03-25 苏州市罗森助剂有限公司 一种高纯分散红60的制备方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6130550A (ja) * 1984-07-19 1986-02-12 Sumitomo Chem Co Ltd １−アミノ−２−フエノキシ−４−ヒドロキシアントラキノン類の製造方法

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4350494A (en) * 1976-01-06 1982-09-21 Ciba-Geigy Corporation Process for the dyeing of textile material and apparatus for carrying out the process
US6028046A (en) * 1997-08-11 2000-02-22 Witco Corporation Detergents with polyamine alkoxylates useful in cleaning dyed fabrics while inhibiting dye transfer
CN104448886A (zh) * 2014-11-24 2015-03-25 苏州市罗森助剂有限公司 一种高纯分散红60的制备方法

Also Published As

Publication number Publication date
GB1141156A (en) 1969-01-29
DE1619381A1 (de) 1971-06-03
JPS516265B1 (forum.php) 1976-02-26
CH643166A4 (forum.php) 1968-11-29
CH469859A (de) 1969-04-30
FR1478768A (fr) 1967-04-28

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