US3706530A - Process for the dyeing of textile material with dye carrier of predominantly higher boiling alkyl benzenes - Google Patents

Process for the dyeing of textile material with dye carrier of predominantly higher boiling alkyl benzenes Download PDF

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Publication number
US3706530A
US3706530A US42578A US3706530DA US3706530A US 3706530 A US3706530 A US 3706530A US 42578 A US42578 A US 42578A US 3706530D A US3706530D A US 3706530DA US 3706530 A US3706530 A US 3706530A
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United States
Prior art keywords
dyeing
dye carrier
dye
mixture
carrier
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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
Application number
US42578A
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English (en)
Inventor
Hans-Peter Baumann
Robert Christian Keller
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Sandoz AG
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Sandoz AG
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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
    • 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
    • D06P1/64—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 without sulfate or sulfonate groups
    • D06P1/651—Compounds without nitrogen
    • D06P1/6515—Hydrocarbons
    • 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
    • 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
    • Y10S8/922—Polyester fiber

Definitions

  • This invention relates to a process for dyeing or printing polyester fibres in the form of loose fibre, yarn or piece goods using disperse dyes in the presence of carriers which contain at least 30% by weight of alkylbenzenes.
  • polyester fibres cannot be satisfactorily dyed by exhaust dyeing methods unless a carrier is present in the dyebath, or unless dyeing is carried out at temperatures above 120 C. under pressure.
  • a great number of carriers have been suggested for this purpose, the best known of which include orthophenylphenol and chlorinated benzenes emulsified in water.
  • polyester fibres and textiles can be dyed and printed with excellent results by using as carrier a mixture of aromatic compounds which consists to at least 30% by weight of alkylbenzenes, in which the benzene nucleus bear two or more methyl radicals or at least one ethyl, propyl or butyl radical as substituents.
  • carrier mixtures which begin to boil preferably at temperatures above 150 (3., leads to dyeings and prints having a levelness (not spotting) superior to those produced in the presence of known carriers for polyester fibres.
  • the new carriers can be obtained, for example, from the residues remaining after distillation in the bulk manufacture of ortho-, metaor para-xylene or other alkylbenzenes.
  • the dye carriers thus obtained generally contain more than 50% by weight of alkylbenzenes, in which the henzene nucleus bears as substituents two or more methyl radicals or at least one ethyl, propyl or butyl radical.
  • the residues left after distillation in the manufacture of the aforenamed products usually contain diphenyl and small amounts of naphthalene, anthracene, phenanthrene and fluorene.
  • the boiling points of these dye carrier mixtures range from 160 C. to 280 C.
  • the last-named compounds can, if desired, be eliminated from the distillation residues, in which case dye carriers are obtained which boil in the region of 160 C. to 185 C.
  • non-water-solubilizing substituents for example diphenyl oxide, benzoic acid methylester, or aromatic compounds containing halogen.
  • non-water-solubilizing substituents are halogen atoms, nitro, cyano, hydroxyl, alkyl and alkoxy groups.
  • the claimed mixtures have a more balanced effect on dyeing than their single components alone.
  • the mixtures dissolve solid dye carriers, such as naphthalene and diphenyl, which, if present in the bath United States Patent 0 ice alone, tend to crystallize and may then interfere with the progress of dyeing.
  • the normal dyeing which includes pad dyeing
  • printing methods for polyester fibres are employed with the carriers conforming to this invention. It is, however, advisable to add the carrier to the dyebath, padding liquor or printing paste in the form of a fine dispersion, or preferably as an aqueous emulsion, in amounts of about 2% to 35% in relation to the weight of the material to be dyed or printed.
  • the emulsions are best prepared with emulsifiers, suitable examples being the adducts of ethylene oxide on alkylphenols, such as nonylphenol and dodecylphenol, or on castor oil, and alkylbenzene sulphonates, dodecylphenoldiphenylether disulphonate, neutralized sulphonates of the condensation products of phenol or naphthalene with formaldehyde, and mixtures of the aforenamed emulsifiers.
  • alkylphenols such as nonylphenol and dodecylphenol, or on castor oil
  • alkylbenzene sulphonates dodecylphenoldiphenylether disulphonate
  • neutralized sulphonates of the condensation products of phenol or naphthalene with formaldehyde and mixtures of the aforenamed emulsifiers.
  • the emulsifier or emulsifier mixture is added to the dye carrier conforming to this invention, or to a mixture of such a carrier and known carriers or solvents, in amounts which generally range from 5% to 30% by weight, or preferably 1525% by weight, on the amount of the carrier.
  • the emulsifier or emulsifier mixture is prepared with an anionic dispersing agent, preferably in an amount greater than 60% by weight, more especially from to by weight, and a non-ionic dispersing agent in amounts of 5% to 15% by weight.
  • anion-active dispersing agents for use with the emulsifiers are those which cause little foaming with the active substance of the carriers of this invention in the dyeing process.
  • anion-active dispersing agents include sulphonated castor oils, sulphonated oleic acid esters, alkylnaphthalene sulphonates, succinic acid diethyl-hexylester sulphonates, xylene sulphonates and toluene sulphonates.
  • non-ionic dispersing agents are fatty acid ethers, arylphenoland alkylphenolpolyglycol ethers; dispersing agents having more than 25-30% ethylene oxide units in a maximum amount of 5% should be present in the emulsifier mixture.
  • Polyglycolether derivatives having approximately 6l5 moles of added ethylene oxide groups occupying an intermediate position, especially if they are partially carboxymethylated.
  • Carboxymethylated polyglycolether derivatives having more than 25 moles of ethylene oxide are comparable in their action to non-carboxymethylated emulsifiers of similar ethylene oxide content.
  • an emulsifier with the highest possible anionic activity is necessary with the active carrier substances of this invention in order to obtain deep dyeings. If the emulsifier mixture contains an over-high percentage of non-ionic emulsifier, it is hardly possible to reach deep black dyeings. Conversely, if the emulsifier is only anion-active (i.e. if the specific sulphonates are dodecylbenzene sulphonates), the dye tends to exhaust too rapidly onto the fibre and the dyeings show inferior rubbing fastness.
  • the emulsifier preparations may either be added directly to the dyebath, padding liquid or printing paste, or they may 'be mixed with a suitable dye and the mixture worked up as a dye preparation.
  • While the process of the present invention is intended primarily for the dyeing of textiles made of polyester fibres of high melting point, it is fundamentally suitable for use with other hydrophobic, poorly dyeable fibres having a large number of ester groups in the molecule, for example cellulose triacetate and linear polyurethanes.
  • the assistants described herein are highly suitable for use in dyeing and printing with disperse, developed and vat dyes, being applicable in the dyeing or printing process itself or as a separate pretreatment.
  • the normal dyeing and printing methods for disperse dyes are employed, the dyes being invariably added to the dyebath in finely dispersed form.
  • the dyed or printed goods can be submitted to a reduction clearing treatment if necessary.
  • a dyebath is set at 40 with 4000 parts of water, 2 g./l. of anhydrous ammonium sulphate, 0.6 part of a finely dispersed mixture of 50% each of the dyes of the formulae 0H and H6 I NH:
  • assistant (b) (1) (see table), which emulsifies in the bath.
  • the pH is adjusted to with formic acid and 100 parts of a fabric of polyester fibre are entered.
  • the temperature is raised to about 97 and the fabric dyed for about 1 hour at this temperature. On removal it is washed off, rinsed and dried. A level, well penetrated blue dyeing is obtained on the polyester fabric which has excellent fastness properties.
  • dyeings of excellent levelness and high fastness can be produced with the dyes of the following formulae yellow CHQCHZOC O CH:
  • the print is dried at 60-100, steamed for 20 minutes,
  • Dye carrier mixtures 1 Percent 1,2,3-trimethylbenzene 1,2,4-trimethylbenzene 25 1,3,5-trimethy1benzene 1,2-ethyltoluene 1,3-ethyltoluene 45 1,4ethyltoluene n-Butylbenzene 10 Sec.-butylbenzene Tert.-butylbenzene 20 1,2,3-trimethylbenzene 5 1,3-5-trimethylbenzene 10 tert.-butylbenzene 1,2,4-trimethylbenzene n ⁇ 16 Sec.buty1benzene Ortho-, meta-, para-ethyltoluene 27 n-Propylbenzene 8 Isopropylbenzene 3 n-Butylbenzene 5 Diphenyl 20 Naphthalene l Anthracene, phenanthrene, fluorene 5 Ethylbenzene 0.5 Para-xylene 1 Meta-x
  • % dye carrier mixture (a) (2), 13% castor oil polyglycolether (30 moles ethylene oxide) and 12% sodium dodecylbenzenesulphonate.
  • the dye carrier is a mixture of aromatic compounds at least 30 percent by weight of which consists of alkylbenzene in which the benzene nucleus bears as substituents two or more methyl radicals or at least one ethyl, propyl or butyl radical, and the mixture boils in the region of from to 280 C.
  • fibre is in the form of loose fibre, yarn or piece goods
  • dye carrier is a mixture of carriers which boils in the region of from 160 to C.
  • the fibre is in the form of loose fibre, yarn or piece goods
  • the dye carrier contains a member selected from the group consisting of diphenyloxide and substituted diphenyloxide, any substituted diphenyloxide being essentially Water insoluble.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Coloring (AREA)
US42578A 1969-07-01 1970-06-01 Process for the dyeing of textile material with dye carrier of predominantly higher boiling alkyl benzenes Expired - Lifetime US3706530A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1004969A CH527325A (de) 1969-07-01 1969-07-01 Verfahren zum Färben von Textilmaterial aus linearen aromatischen Polyestern

Publications (1)

Publication Number Publication Date
US3706530A true US3706530A (en) 1972-12-19

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Application Number Title Priority Date Filing Date
US42578A Expired - Lifetime US3706530A (en) 1969-07-01 1970-06-01 Process for the dyeing of textile material with dye carrier of predominantly higher boiling alkyl benzenes

Country Status (12)

Country Link
US (1) US3706530A (is")
JP (1) JPS5237119B1 (is")
BE (1) BE752539A (is")
CA (1) CA919860A (is")
CH (2) CH527325A (is")
DE (1) DE2033894C3 (is")
ES (1) ES381273A1 (is")
FR (1) FR2060024B1 (is")
GB (1) GB1308965A (is")
HK (1) HK52176A (is")
MY (1) MY7600250A (is")
NL (1) NL164343C (is")

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3807953A (en) * 1971-05-28 1974-04-30 Sandoz Ltd Method of disperse dyeing and carrier composition therefor
US3925013A (en) * 1973-05-23 1975-12-09 Catawba Chemicals Inc Eutectic biphenyl-napthalene dye carriers
US3976427A (en) * 1972-05-23 1976-08-24 Sandoz Ltd. Organic compounds
US4252534A (en) * 1978-10-19 1981-02-24 Ciba-Geigy Corporation Dyeing assistants and their use in dyeing synthetic fibre material
US4345910A (en) * 1980-03-05 1982-08-24 Basf Aktiengesellschaft Dyeing of NCD polyester fibers
US4350493A (en) * 1980-03-27 1982-09-21 Sandoz Ltd. Carrier composition for disperse dyes

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5418519U (is") * 1977-07-11 1979-02-06

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2670263A (en) * 1951-03-21 1954-02-23 Gen Dyestuff Corp Composition and process for dyeing polyethylene terephthalate fibers
FR1261119A (fr) * 1960-06-28 1961-05-12 Chem Fab Gruenau Veb Procédé améliorant l'aptitude tinctoriale de fibres de polyesters
FR1525827A (fr) * 1967-06-07 1968-05-17 Compositions auxiliaires pour la teinture des matières textiles

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3807953A (en) * 1971-05-28 1974-04-30 Sandoz Ltd Method of disperse dyeing and carrier composition therefor
US3976427A (en) * 1972-05-23 1976-08-24 Sandoz Ltd. Organic compounds
US3925013A (en) * 1973-05-23 1975-12-09 Catawba Chemicals Inc Eutectic biphenyl-napthalene dye carriers
US4252534A (en) * 1978-10-19 1981-02-24 Ciba-Geigy Corporation Dyeing assistants and their use in dyeing synthetic fibre material
US4345910A (en) * 1980-03-05 1982-08-24 Basf Aktiengesellschaft Dyeing of NCD polyester fibers
US4350493A (en) * 1980-03-27 1982-09-21 Sandoz Ltd. Carrier composition for disperse dyes

Also Published As

Publication number Publication date
NL164343B (nl) 1980-07-15
DE2033894B2 (de) 1979-04-05
DE2033894C3 (de) 1979-11-22
NL7008997A (is") 1971-01-05
CH527325A (de) 1972-05-15
MY7600250A (en) 1976-12-31
JPS5237119B1 (is") 1977-09-20
ES381273A1 (es) 1973-04-01
CA919860A (en) 1973-01-30
DE2033894A1 (de) 1971-01-14
CH1004969A4 (is") 1972-05-15
GB1308965A (en) 1973-03-07
NL164343C (nl) 1980-12-15
BE752539A (fr) 1970-12-01
FR2060024A1 (is") 1971-06-11
FR2060024B1 (is") 1974-02-01
HK52176A (en) 1976-08-27

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