US3203751A - Process of dyeing polyester fibers with diamino-anthraquinone-carbonitrile dyestuffs - Google Patents

Process of dyeing polyester fibers with diamino-anthraquinone-carbonitrile dyestuffs Download PDF

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Publication number
US3203751A
US3203751A US296493A US29649363A US3203751A US 3203751 A US3203751 A US 3203751A US 296493 A US296493 A US 296493A US 29649363 A US29649363 A US 29649363A US 3203751 A US3203751 A US 3203751A
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United States
Prior art keywords
dyestuffs
dyeing
diamino
dyestuff
anthraquinone
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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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US296493A
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English (en)
Inventor
Hildreth John David
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Novartis Corp
Original Assignee
Toms River Chemical Corp
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Filing date
Publication date
Priority to BE650748D priority Critical patent/BE650748A/xx
Application filed by Toms River Chemical Corp filed Critical Toms River Chemical Corp
Priority to US296493A priority patent/US3203751A/en
Priority to CH732564A priority patent/CH414530A/de
Priority to FR981905A priority patent/FR1401010A/fr
Priority to DET26642A priority patent/DE1264386B/de
Priority to GB30706/64A priority patent/GB1022220A/en
Application granted granted Critical
Publication of US3203751A publication Critical patent/US3203751A/en
Assigned to CIBA-GEIGY CORPORATION reassignment CIBA-GEIGY CORPORATION MERGER (SEE DOCUMENT FOR DETAILS). Assignors: TOMS RIVER CHEMICAL CORPORATION
Assigned to CIBA-GEIGY CORPORATION, A CORP. OF N.Y. reassignment CIBA-GEIGY CORPORATION, A CORP. OF N.Y. MERGER (SEE DOCUMENT FOR DETAILS). EFFECTIVE DATE: NOV. 2,1981, STATE OF INCORP. NEW YORK, Assignors: TOMS RIVER CHEMICAL CORPORATION
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
    • 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
    • D06P3/34—Material containing ester groups
    • D06P3/52—Polyesters
    • D06P3/54—Polyesters using dispersed dyestuffs
    • 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
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/22—Dyes with unsubstituted amino groups
    • 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
    • D06P3/82—Textiles which contain different kinds of fibres
    • D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
    • D06P3/8223—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups
    • D06P3/8238—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using different kinds of dye
    • D06P3/8252—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using different kinds of dye using dispersed and reactive dyes

Definitions

  • This invention relates to the production of valuable dyeings on fibrous materials of aromatic polyesters, and more particularly to dyed polyethylene terephthalate fibers of excellent color strength and good fastness properties.
  • Polyester fibers present particular dyeing problems, arising at least in part out of the hydrophobic nature of such fibers.
  • the class of dyes known as disperse dyestuffs has come to have the widest application. These dyestuffs are essentially water-insoluble products applied in a finely divided condition from a dispersion.
  • the dyeing difiiculties associated with polyester fibers have been met by the development of special methods for the application of disperse dyes to the fibers. Of these methods, the one known as the Pad/Thermofix method has become of increasing importance since it is particularly adapted for high-speed, continuous dyeing operations.
  • a fabric is padded by passing it through an aqueous suspension of the dyestuff and squeezing the fabric between closely-set rollers in order to remove excess dye liquor.
  • the dyestulf is only loosely attached to the fiber at this point.
  • the dyestuff is then fixed on the fiber by subjecting the material to a short, intensive heat-treatment at elevated temperatures of the order of about 120220 C. It is evident that a dyestuff, in order to be suitable for application by this method, must be fast to sublimation or else it will wholly or partially volatilize from the fiber during the heattreatrnent step. The result of such sublimation will be a loss of color value on the polyester fiber and, if a union dyeing operation is being carried out, the staining of the other fibers, such as cotton, which may be present in the blend.
  • R is cyano and R is hydrogen or cyano.
  • the 1,4-diaminoanthraquinonecarbonitriles employed in the practice of the present invention can be obtained in known manner by heating the appropriate 1,4-diaminoanthraquinonesulfonic acid in water with an alkali metal cyanide.
  • the single dyestuffs there can be used a mixture of the two dyestuffs or a mixture of such dyestuff with a dyestuff of similar structure.
  • the said dyestuffs are preferably used in a finely divided form and the dyeing is carried out in the presence of a dispersing agent, such as sulphite cellulose waste liquor or a synthetic detergent, or a combination of different wetting and dispersing agents.
  • a dispersing agent such as sulphite cellulose waste liquor or a synthetic detergent, or a combination of different wetting and dispersing agents.
  • Dyestuff preparations of this kind can be made by known methods, for example, by grinding the dyestuff(s) either in dry or wet form with or without the addition of a dispersing agent.
  • the dyestuffs used in the invention are especially suitable for dyeing by the so-called thermofixation or Pad/Thermofix method, in which the fabric to be'dyed is impregnated advantageously at a temperature not exceeding 60 C. with an aqueous dispersion of the dyestuff, which may contain 1 to 50% of urea and a thickening agent, especially sodium alginate, and the fabric is squeezed in the usual manner.
  • the squeezing is preferably carried out so that the goods retain 50 to of their weight of dye liquor.
  • the dyestutf is fixed by subjecting the impregnated fabric to a heat treatment at temperatures above 100 C., for example, at a temperature ranging from 220 C., it being of advantage to dry the fabric prior to this treatment, for example, in a current of warm air.
  • the padding liquor contains a dyestuff suitable for dyeing cotton, for example, a direct dyestutf or vat dyestuif, or more especially a so-called reactive dyestuff, i .e. a dyestuff capable of being fixed on cellulose fibers with the formation of a chemical bond, for example, a dyestuif containing a chlorotriaziue or chlorodiazine residue.
  • a dyestuff suitable for dyeing cotton for example, a direct dyestutf or vat dyestuif, or more especially a so-called reactive dyestuff, i .e. a dyestuff capable of being fixed on cellulose fibers with the formation of a chemical bond, for example, a dyestuif containing a chlorotriaziue or chlorodiazine residue.
  • an agent capable of binding acid for example, an alkali carbonate, alkali phosphate, alkali borate or alkali perborate, or a mixture of": two or more of these agents.
  • an agent capable of binding acid for example, an alkali carbonate, alkali phosphate, alkali borate or alkali perborate, or a mixture of": two or more of these agents.
  • the dyeings produced on polyester fibers by the process of the invention are advantageously given an after-treatment, for example, by heating them with an aqueous solution of a non-ionic detergent.
  • the process is also suitable for dyeing mixed fabrics of polyester fibers and wool and the wool portion which remains reserved, may be subsequently dyed with a wool dyestulf.
  • the dyestuffs in the process may be applied by printing.
  • a printing color is used'which, in addition to the usual printing assistants, such as wetting and thickening agents, contains the finely dispersed dyestuff, if desired, in admixture with one of the aforesaid cotton dyestuffs, and, if desired, in the presence of urea and/or an agent capable of binding acid.
  • polyester defines synthetic polymeric polyesters, such as the highly polymeric linear polyesters, the molecules of which have recurring monomeric units connected by ester linkages.
  • Dibasic acids for example, aromatic acids, such as terephthalic acid, diphenyl-4,4'-dicarboxylic acid and/or diphenylsulfone-4,4'-dicarboxylic acid and dihydroxy compounds, for example, glycols, such as ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol and/ or butylene glycol, as well as other diols, such as 1,4-cyclohexyldiol can be used as the monomers to form the polymeric polyesters.
  • Typical commercial examples of such fibers are Dacron, Terylene, Fortrel, Trevira, Terlanca, Kodel, Vycron, etc. They are disclosed, for example, in US. Patent No. 2,901,466 and British Patents Nos. 578,079; 579,462; 588,411; 588,497 and 596,688.
  • the present invention is, of course, equally applicable to the dyeing of blends of polyester fibers and cellulosic fibers.
  • the latter term includes native cellulose, such as linen or, more particularly, cotton, as well as regenerated cellulose, such as viscose or cuprammonium rayon.
  • Example 1 366 parts of 1,4-diamino-2,3-anthraquinonedisulfonic acid, sodium salt is added to 14,500 parts of water, stirred and adjusted to a pH of 10.6 at 75 C. by the addition of 30% sodium hydroxide solution. 226.5 parts of sodium cyanide is then added and the mixture stirred for 6 hours at 75-80 C. At the end of this period, the reac tion mixture is filtered hot at 60 C., washed with 1,500 parts hot (60 C.) water and dried. The product is obtained in a yield of 170 parts.
  • the product gives a reddish-orange vat with caustic soda and hydrosulfite, a pale greenish solution in concentrated sulfuric acid, turning yellower on addition of formaldehyde and has a melting point above 330 C.
  • the product comprises 1,4-diamino-2,3-anthraquinonedicarbonitrile in admixture with other carbonitrile derivatives of 1,4-diaminoanthraquinone, principally 1,4-diamino-2-anthraquinonecarbonitrile.
  • Example 2 60 parts 1,4-diamino-2-anthraquinonesulfonic acid (prepared by the hydrolysis of 1-amino-4-p-toluenesulfonamido-anthraquinone-Z-sulfonic acid, potassium salt with 96% H SO is added to 1,250 parts water. 40 parts of sodium cyanide and 20 parts ammonium bicarbonate are then added and the whole stirred for 5 hours at 95l00 C., the color changing from a bluish-violet to a purple. After cooling, the reaction mixture is filtered and the product, separated by filtration, is washed with hot water and dried. The yield is 40 parts.
  • the product gives a reddish-orange vat with caustic soda and hydrosulfite, a pale greenish solution in concentrated sulfuric acid, turning yellower on addition of formaldehyde and has a melting point above 330 C.
  • the product comprises 1,4-diamino-2-anthraquinonecarbonitrile in admixture with other 1,4-diaminoanthraquinonecarbonitrile derivatives, principally the 1,4-diamino-2,3-anthraquinonedicarbonitrile.
  • Example 3 parts of the dyestuff of Example 1 are brought to a state of fine dispersion by milling in a ball mill with 19:. 3.0 parts of the condensation product of naphthalene-2- sulfonic acid with formaldehyde, and 37 parts of water.
  • Amounts of this preparation, sufiicient to provide a concentration of 1.5, 3.0 and 6.0 grams of dyestutf per liter of dye bath, is finely dispersed in water containing 10.0 g. of sodium alginate per liter and the resultant pad liquor is brought to a temperature of 25 C.
  • Polyethylene terephthalate fabric is then padded with the above liquor and mechanically squeezed to a 65% pick up.
  • the padded material is then air dried and developed by dry heat, curing in an electrically-heated, hotair drier for 1 minute at 200 C.
  • the dyed fabric is scoured for 5 minutes at the boil in a solution containing 3% of sodium di-iso-butylnaphthalene monosulfonate and 5% sodium carbonate and then dried.
  • a bright blue dyeing is obtained, characterized by good penetration and excellent fastness to light and sublimation.
  • Example 4 The procedure of Example 3 is repeated, except that the dyestutf of Example 2 is used in place of the dyestuff of Example 1. A bright blue dyeing of slightly redder shade is obtained, characterized by good penetration and excellent fastness to light and sublimation.
  • Example 5 The procedure of Example 3 is repeated, except that 1,4-diamino-2,3-anthraquinonedicarbonitrile is used instead of the dyestutf of Example 1. A bright blue dyeing of excellent light and sublimation fastness and good penetration characteristics is obtained.
  • Example 6 The procedure of Example 3 is repeated, except that 1,4-diaminoanthraquinone-Z-carbonitrile is used instead of the dyestuff of Example 1. A bright blue dyeing of good light and sublimation fastness and good penetration characteristics is obtained.
  • Polyester fiber according to claim 1 wherein R and R are both cyano, that is, the anthraquinone compound is 1,4-diamino-2,3-anthraquinonedicarbonitrile.
  • Polyester fiber according to claim 1 in which the polyester fiber is polyethylene terephthalate.
  • polyester fiber according to claim 2 in which the polyester fiber is polyethylene terephthalate.
  • Polyester fiber according to claim 3 in which the polyester fiber is polyethylene terephthalate.
  • a process of dyeing and printing a polyester material which comprises applying to fibrous material of synthetic polyester an aqueous dispersion containing a 1,4-diaminoanthraquinonecarbonitrile of the formula 5 wherein R is a member selected from the group consisting of hydrogen and cyano and R is cyano, as the essential color imparting substance.
  • a process of dyeing and printing a polyester material which comprises applying to fibrous material of synthetic polyester an aqueous dispersion containing as the essential color imparting substances a mixture of 1,4- diamino-2,3-anthraquinonedicarbonitrile and 1,4-diamino- 2-anthraquinonecarbonitrile.
  • anthraquinone compound is 1,4-diarnino-2,3-anthraquinonedicarbonitrile.

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  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
US296493A 1963-07-22 1963-07-22 Process of dyeing polyester fibers with diamino-anthraquinone-carbonitrile dyestuffs Expired - Lifetime US3203751A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
BE650748D BE650748A (de) 1963-07-22
US296493A US3203751A (en) 1963-07-22 1963-07-22 Process of dyeing polyester fibers with diamino-anthraquinone-carbonitrile dyestuffs
CH732564A CH414530A (de) 1963-07-22 1964-06-04 Verfahren zum Färben oder Bedrucken von Polyesterfasern mit 1,4-Diamino-2,3-dicyan-anthrachinon
FR981905A FR1401010A (fr) 1963-07-22 1964-07-16 Procédé pour teindre des fibres de polyesters
DET26642A DE1264386B (de) 1963-07-22 1964-07-21 Verfahren zum Faerben oder Bedrucken von Polyesterfasern
GB30706/64A GB1022220A (en) 1963-07-22 1964-08-04 Dyeing of polyester fibres

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US296493A US3203751A (en) 1963-07-22 1963-07-22 Process of dyeing polyester fibers with diamino-anthraquinone-carbonitrile dyestuffs

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US3203751A true US3203751A (en) 1965-08-31

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US296493A Expired - Lifetime US3203751A (en) 1963-07-22 1963-07-22 Process of dyeing polyester fibers with diamino-anthraquinone-carbonitrile dyestuffs

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US (1) US3203751A (de)
BE (1) BE650748A (de)
CH (1) CH414530A (de)
DE (1) DE1264386B (de)
GB (1) GB1022220A (de)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4042605A (en) * 1975-06-04 1977-08-16 Basf Aktiengesellschaft Process for the production of 1,4-diaminoanthraquinone-2,3-dinitrile
US4299771A (en) * 1979-10-26 1981-11-10 Sumitomo Chemical Company, Limited Process for producing anthraquinone compounds
DE3642052A1 (de) * 1985-12-10 1987-06-11 Sumitomo Chemical Co Verfahren zur herstellung von anthrachinon-verbindungen
WO2001018104A1 (en) * 1999-09-10 2001-03-15 General Electric Company Resinous compositions containing blue dye
US20010031590A1 (en) * 2000-04-14 2001-10-18 Wolfgang Schulz Wning fabric and process for producing same

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1938028A (en) * 1928-11-08 1933-12-05 Firm Chiffriermaschinen Ag Electrical coding and de-coding device
US2757064A (en) * 1953-04-16 1956-07-31 Du Pont Polyester fibers dyed with anthraquinone dyes
US3084015A (en) * 1959-10-30 1963-04-02 Ciba Ltd Process for dyeing or printing fibrous materials of aromatic polyesters

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2692272A (en) * 1951-12-05 1954-10-19 Du Pont 1, 4-diamino-2, 3-anthraquinonedicarboxamides

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1938028A (en) * 1928-11-08 1933-12-05 Firm Chiffriermaschinen Ag Electrical coding and de-coding device
US2757064A (en) * 1953-04-16 1956-07-31 Du Pont Polyester fibers dyed with anthraquinone dyes
US3084015A (en) * 1959-10-30 1963-04-02 Ciba Ltd Process for dyeing or printing fibrous materials of aromatic polyesters

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4042605A (en) * 1975-06-04 1977-08-16 Basf Aktiengesellschaft Process for the production of 1,4-diaminoanthraquinone-2,3-dinitrile
US4299771A (en) * 1979-10-26 1981-11-10 Sumitomo Chemical Company, Limited Process for producing anthraquinone compounds
DE3642052A1 (de) * 1985-12-10 1987-06-11 Sumitomo Chemical Co Verfahren zur herstellung von anthrachinon-verbindungen
US4784806A (en) * 1985-12-10 1988-11-15 Sumitomo Chemical Company, Limited Method for producing anthraquinone compounds
WO2001018104A1 (en) * 1999-09-10 2001-03-15 General Electric Company Resinous compositions containing blue dye
US6245118B1 (en) * 1999-09-10 2001-06-12 General Electric Company Resinous compositions containing blue dye
US20010031590A1 (en) * 2000-04-14 2001-10-18 Wolfgang Schulz Wning fabric and process for producing same

Also Published As

Publication number Publication date
BE650748A (de)
DE1264386B (de) 1968-03-28
CH414530A (de) 1966-12-30
CH732564A4 (de) 1966-01-31
GB1022220A (en) 1966-03-09

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Effective date: 19811102