US3619124A - Process for the dyeing or printing of fibrous materials - Google Patents

Process for the dyeing or printing of fibrous materials Download PDF

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Publication number
US3619124A
US3619124A US872744A US3619124DA US3619124A US 3619124 A US3619124 A US 3619124A US 872744 A US872744 A US 872744A US 3619124D A US3619124D A US 3619124DA US 3619124 A US3619124 A US 3619124A
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US
United States
Prior art keywords
dyeing
carbon atoms
compound
dyestuffs
dyestuff
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
Application number
US872744A
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English (en)
Inventor
Gerhard Weckler
Helmut Diery
Lorenz Heib
Franz Schon
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Hoechst AG
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Hoechst AG
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Publication date
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Publication of US3619124A publication Critical patent/US3619124A/en
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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
    • D06P3/82—Textiles which contain different kinds of fibres
    • D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
    • D06P3/8214—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing ester and amide groups
    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0084—Dispersions of dyes
    • C09B67/0085—Non common dispersing agents
    • 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
    • D06P1/60—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 polyethers
    • D06P1/613—Polyethers without nitrogen
    • 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
    • Y10S8/907—Nonionic emulsifiers for dyeing

Definitions

  • the present invention is concerned with the use of polyalkylene oxide compounds as dispersing, levelling or aftertreating agents in a process for the dyeing or printing of fibrous materials.
  • Such unsatisfactory results are, e.g., experienced in the dyeing of cellulose fibers with vat dyestuffs, their leucosulfuric acid esters, other organic or inorganic pigments or developing dyestuffs, or when synthetic fibers, preferably polyester fibers are dyed with pigment dyestufis, for example, disperse dyestuffs.
  • Another problem rendering difficult the dyeing of blends of polyester fibers and wool or cellulose fibers with dispersion dyestuffs consists in that the second fiber is stained and that the dyed fabric thus has inferior fastness properties.
  • dyestuffs which are insoluble or sparingly soluble in water can be maintained in the form of fine dispersions during the dyeing process, when additives such as the condensation products of naphthalene-sulfonic acid with formaldehyde or the alkali metal salts thereof, oxethylated fatty alcohols, etc., are used.
  • additives such as the condensation products of naphthalene-sulfonic acid with formaldehyde or the alkali metal salts thereof, oxethylated fatty alcohols, etc.
  • the applicability of these compounds for the production of dyeings is almost always limited to a specific application field so that for different dyestuff classes or different dyeing processes using the same dyestuffs or for aftertreating such dyeings different auxiliaries are required.
  • the products mentioned either possess solely dispersing properties or solely levelling properties, so that combination of both actions is achieved almost exclusively with mixtures of various auxiliaries only.
  • polyalkyleneoxide compounds having the general formula and n stands for a number of three to about 200, preferably three to about 100, especially seven to about 70, can be used universally as dispersing, levelling or aftertreating agents for dyeing or printing fibrous materials consisting of cellulose, cellulose triacetate, polyamide fibers of natural or synthetic origin or hydrophobic fibers, for example fibers of polyester or polyacrylonitrile or their copolymers or of mixtures of said fibers, with dyestuffs insoluble or sparingly soluble in water.
  • Said addition compounds are obtained by stirring the two components at temperatures ranging from l0 to C. in the presence of Friedel-Crafts catalysts US. application Ser. No. 841,620, filed July 14, 1969 discloses the synthesis of the above emulsifiers in detail.
  • polyalkylene oxide compounds of formula I there have proved suitable for the application according to the present invention, for example, in particular the addition products of bis-chloromethyl ether of a polyethylene glycol with a molar weight of about l00 to 2,000 on octene-l, dodecene-l, octadecene-l or on a technical mixture of aolefins containing from about 15 to 18 carbon atoms.
  • bromomethyl or chloromethyl ether of a methoxy polyethyleneglycol with two to 50 ethoxyl groups on dodecene-l, octadecene-l or on a technical mixture of an aolefin having from 15 to 22 carbon atoms.
  • Such polyethylene glycols may, for example, also contain instead of the methylether group a lauryl-, oleylor octadecylether group or a phenyl-, naphthylor benzylether radical.
  • the polyethyleneglycol serving as starting compound may be unilaterally esterified with a carboxylic, preferably, a fatty acid having up to 18 carbon atoms, e.g., acetic or stearic acid, or benzoic acid.
  • a carboxylic preferably, a fatty acid having up to 18 carbon atoms, e.g., acetic or stearic acid, or benzoic acid.
  • the alkyl radical of the alkylphenol serving as starting compound contains up to 12 carbon atoms.
  • the amount of polyalkyleneoxide compound used ranges in the present process between 0.1 and 5 g., preferably 0.5 to 2 g. per liter of aqueous dye or aftertreating bath.
  • the action of these products is not dependent on a definite temperature or pH value.
  • dyestuffs insoluble or sparingly soluble in water there are understood those selected from the group consisting of vat dyestuffs, their leucosulfuric acid esters, inorganic or organic pigment dyestuffs, developing dyestuffs or disperse dyestuffs, anionic or cationic dyestuffs, more especially dyestuffs of the azo, indanthrone, anthraquinone, quinophthalone, triphenylmethane or polymethine series.
  • EXAMPLE 1 Aqueous solutions were prepared each from 2 gjl. of dyestuff Cl 69 826-Solubilized Vat Blue 6 (cf. Color index, 2nd edition (1956), volume 3, page 3,535) and increasing amounts (/O.2/0.4/0.6/0.8/l.0 g./l.) of the addition product of 1 mol of the bis-chloromethylether ofa polyethyleneglycol of a molecular weight of 1,200 and 2 mols ofa technical mixture of a-olefins with 15 to 18 carbon atoms (referred to hereinafter as compound A). Subsequently thereto, the dis solved dyestuff was transformed into its pigment form by oxidizing with sulfuric acid and sodium nitrite.
  • the so-obtained dyestuff dispersions were, after abandoning for half an hour. suction-filtered through a round filter (Schleicher and Schull. No. 1450). The resulting residues of the filter samples showed how the dispersive power rose with the amount of compound A increasing, in the case of the above-mentioned dyestuff class.
  • the so-obtained dispersion of the developing dyestuff was allowed to stand for about minutes whereupon it was suction-filtered through a round filter (Schleicher and Schiill No. 1450).
  • the resulting residues of the filter samples showed that increased addition of compound A enabled a 30 higher dispersing effect.
  • EXAMPLE 5 One hundred parts of a cotton fabric were dyed on a jigger at a goods-to-liquor ratio 1:5 by treating in the following aqueous baths:
  • the fabric was first impregnated for 45 minutes in a bath which had cooled off, starting at a temperature of C. and using liquor (a), whereupon it was squeezed off and the dyestufi developed cold for 30 minutes, without intermediate rinsing, by treating with liquor (b).
  • liquor (a) the dyestufi developed cold for 30 minutes, without intermediate rinsing, by treating with liquor (b).
  • the dyeing was finished according to the method usual with this class of dyestuffs, i.e. soaped twice at 60 C. and at the boil.
  • EXAMPLE 6 Four hundred g. of a combed material made from polyethyleneglycolterephthalate fibers were dyed. as closely packed as possible in a high-temperature dyeing machine at l C. over the course of 90 minutes at a goods-to-liquor ratio lz40 with an aqueous liquor containing (referred to the dry weight of the goods) 0.04 I; of the disperse tlycstulf of formula O /l i HO] kl CH L N F 0.027% of the disperse dyestuff of formula 0.02% of the disperse dyestuff of formula EXAMPLE 7 One hundred g.
  • EXAMPLE 8 To aqueous dyestufi' solutions of 3 g./l. of the anionic dyestuff Acid Blue 213 (cf. Color Index. 2nd edition, Sup lement volume (1963). page 81) and l ml./l. of acetic am of 30 percent strength increasing amounts (/0.2/0 4/0.6 /0.8/l.0 g./l.) of compound A were added. Subsequently, these solutions were mixed each with 3 g./l. of the cationic dyestuff Basic Yellow 21 (cf. Color Index. 2nd edition, Supplement volume (1963). page 15] and heated to about C. at which temperature they were abandoned for about 30 minutes. The the individual samples were suction-filtered using a round filter (Schleicher andSchiill,No. 1450).
  • a process for dyeing or printing of fibrous materials consisting of cellulose. cellulose triacetate, natural or synthetic polyamide. polyester or polyacrylonitrile fibers or mixtures thereof with water-insoluble or sparingly soluble dyestuffs, which comprises using as a dyeing auxiliary a compound of the formula in which R is alkyl of four to 20 carbon atoms.
  • X is chlorine or bromine
  • n is a number of three to about 200
  • R is an aliphatic hydrocarbon radical of up to 20 carbon atoms.
  • R is alkyl of

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Dispersion Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
US872744A 1968-11-04 1969-10-30 Process for the dyeing or printing of fibrous materials Expired - Lifetime US3619124A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1640568A CH531611A (de) 1968-11-04 1968-11-04 Verwendung von Polyalkylenoxydverbindungen als Dispergier-, Egalisier- und Nachbehandlungsmittel beim Färben von Textilfasern

Publications (1)

Publication Number Publication Date
US3619124A true US3619124A (en) 1971-11-09

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Application Number Title Priority Date Filing Date
US872744A Expired - Lifetime US3619124A (en) 1968-11-04 1969-10-30 Process for the dyeing or printing of fibrous materials

Country Status (11)

Country Link
US (1) US3619124A (no)
AT (1) AT299117B (no)
BE (1) BE741248A (no)
CH (2) CH1640568A4 (no)
DE (1) DE1953331C3 (no)
FR (1) FR2022544B1 (no)
GB (1) GB1278975A (no)
NL (1) NL6916357A (no)
NO (1) NO127765B (no)
SE (1) SE356772B (no)
ZA (1) ZA697750B (no)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4302202A (en) * 1979-10-09 1981-11-24 Northwestern Laboratories, Inc. Textile treating composition and method of use thereof

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3116581A1 (de) * 1981-04-27 1982-12-30 Hoechst Ag, 6000 Frankfurt Verwendung von veresterten oxalkylaten als praeparationsmittel fuer farbstoffe und entsprechende farbstoffzubereitungen

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2878294A (en) * 1954-01-08 1959-03-17 Quaker Chemical Products Corp Polymeric acetals
US3085987A (en) * 1959-09-21 1963-04-16 Du Pont Linear polyester containing a diaryl ether and process of producing same
US3342542A (en) * 1967-09-19 Ho o nhx c chax c chjx o oh

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3342542A (en) * 1967-09-19 Ho o nhx c chax c chjx o oh
US2878294A (en) * 1954-01-08 1959-03-17 Quaker Chemical Products Corp Polymeric acetals
US3085987A (en) * 1959-09-21 1963-04-16 Du Pont Linear polyester containing a diaryl ether and process of producing same

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4302202A (en) * 1979-10-09 1981-11-24 Northwestern Laboratories, Inc. Textile treating composition and method of use thereof

Also Published As

Publication number Publication date
GB1278975A (en) 1972-06-21
DE1953331C3 (de) 1974-09-12
AT299117B (de) 1972-06-12
CH1640568A4 (no) 1972-08-31
BE741248A (no) 1970-05-04
CH531611A (de) 1972-08-31
FR2022544A1 (no) 1970-07-31
NO127765B (no) 1973-08-13
DE1953331A1 (de) 1970-08-27
FR2022544B1 (no) 1974-03-15
DE1953331B2 (de) 1974-01-24
NL6916357A (no) 1970-05-08
SE356772B (no) 1973-06-04
ZA697750B (en) 1971-03-31

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