US2610103A - Dyeing processes for wool and preparations therefor - Google Patents

Dyeing processes for wool and preparations therefor Download PDF

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Publication number
US2610103A
US2610103A US139794A US13979450A US2610103A US 2610103 A US2610103 A US 2610103A US 139794 A US139794 A US 139794A US 13979450 A US13979450 A US 13979450A US 2610103 A US2610103 A US 2610103A
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United States
Prior art keywords
ortho
dyeing
dyebath
acid
formula
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Expired - Lifetime
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US139794A
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English (en)
Inventor
Widmer Willi
Schuetz Fritz
Heckendorn Alphonse
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BASF Schweiz AG
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Ciba 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
    • 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
    • D06P3/14—Wool
    • D06P3/20—Wool using mordant dyes using metallisable dyes
    • 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
    • Y10S534/00—Organic compounds -- part of the class 532-570 series
    • Y10S534/01—Mixtures of azo compounds
    • 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

Definitions

  • Ortho:ortho'-dihydroxymonoazo dyestuffs which are of relatively good solubility in a neutral to alkaline medium but are of insufficient solubility in an acid medium. Accordingly these dyestuffs can as a rule not be dyed in a useful process from an acid bath because for the most part they are precipitated by the acid in relatively coarse form and thus even if they still take on the fiber from the suspension, they give non-uniform dyeings and as a rule dyeings of poor fastness properties, for example fastness to rubbing. Moreover undesired deposits frequently occur in the dyebath and espe cially on the wallsof the dye vat. However many dyestuffs of.
  • Such'dyestufisare for example the monoazo dyestuffs free from sulfonic cid andcarboxylfgroups but containing a single nitro group of the 'generalformula I011 (1 3 TN;NTT l r wherein R1 and, R2 both indicate an aromatic radical of the benzene series in which the azo group and the hydroxyl group are.
  • OIthOiOIthO'edihydroxymonoazo dyestuffs which are suitable for dyeing fromla neutral to weakly alkaline but not from 'anacid bath, ar'eithose which are. free from sulfonic acid andcarboxyl groups and contain in the moleculeasingle sulfonic acid amide group (ortho:ortho'-dihydroxymonoazo dyestuffs with more than one sulfonic acid amidegroup areas a rule also suificiently soluble fordyeing from an acidbath).
  • dyestuffs of this-'type those orthocortho dihydroxymonoazo dyestuifs'which contain the radical of a dihydroxynaphthalene.
  • a numberof orthozortho' dihydroxymonoazo dyestuffs which are suitable for dyeing from -a neutral to weakly alkalinebut 'notfrom an acid bath, are known (-see forexampleGerman PatentNo. 445,888). Further such dyestuffs can be produced by-methods known perse. Those of thelast given formula can-be obtained'for exampleb'y coupling 'a diazo compound of an amine of the general formula a ll-Uzi fl 0H,
  • R1 indicates an aromatic radicalof the benzene series. inwhich therhy'droxyl group and theamino group are in orthozposition tonone another, with hydroxybenzenesy coupling in orthoposition toltl'ie hydroxyl groups startingmaterials being employed which are free from sulfonic acid,
  • the mentioned ortho:ortho-dihydroxyazo dyestufis containing-sulfonic acidamide groups can be produced by coupling ortho-hydroxydiazo compounds (in this case also preferably such of the benzene series) with-compounds coupling in adjacent position to a hydroxyl' group, as for example lrphe ylfi:methrlefi-nrmzobnes 1W1 droxy-na h halen srsta tins m ialsib n emr' p yed -W 011 ar tree from-sulfim aci la ldl ca of ortho ortho dihydroxymonoazo dyestuffs which are suitable for dyeing from a neutral to weakly alkaline but not from an acid baththere are concerned for example: 4- or -nitro 2- amino-l-hydroxybenzene, 5-nitro 4 methyl-2- amino-l-hydroxybenzene; 6-acetylamino-4-nitro- Z-amino
  • Such dyestuffs are; as arule suitable for, dye.- ing, especially for the dyeing of wool from aneurtralto weakly alkaline bath. Theyare primarily suitable for dyeing by the known single bath chrom ing process, in which, dyeing iscarriedout in the presence ofxanlalka n chromate nd of ammonium sulfate and in; whichv in contradistinction to certain;earlier -literature references-sit is notanacid butenormally a; neutral to weakly l l ne dyeba-th which S;used:-
  • ortho:ortho-dihydroxymonoazo dyestuffs suitable per se for dyeing from antacid bath and in the presence of which vdyeingis conducted in accordance with the present .process suitably such are employed aswcontain as solubilizing groups a carboxyl group or. a sulfonic: acid group or the atom grouping i1 ortho ortho dihydroxyazo dyestuffs 4 Color Index under Nos, 172'; 202 and 652, and the dyestuffs of the formula OH OH I (IF-CH:
  • the ratio ofthe quantity of thedyestuff not suitable for dyeing from an acid bath to thequantity. of the dyestufi. which is suitable for dyein froman acid bath can inthe presentprocessovary within widelimits.
  • Ingeneralit is adyantageous to carry outthe dyeing according to the present process in the presence of a weak acid, preferably in the presence of acetic acid and in the absence of mineral acid.
  • a weak acid preferably in the presence of acetic acid and in the absence of mineral acid.
  • the preparation of the dyebaths servingfor the execution ofrthe present process suitably takes place using the customary stock solutions which contains the dyestuffs dissolved in the desired mixture ratio 'andliinvconsiderably higher con:- centration than is customary for "the dyebaths themselves. If desired the acid can subsequently be added to such stock solution which are suitably of approximately neutral reaction.
  • dye preparations are characterized in that they contain an orthozortho -dihye droxymonoazo dyestufi which per se is suitable for dyeing from a neutral to weakly alkaline but not from an acid bath and an ortho:ortho'- dihydroxymonoazo dyestufi suitable per se for dyeing from an acid bath.
  • the present process and the preparations of the specified constitution suitable for carrying it out are primarily suitable for the dyeing of animal fibers, especially for the dyeing of W001 and preferably of loose wool or carded wool.
  • the ortho:ortho'-dihydroxymonoazo dyestuffs which are per se unsuitable for dyeing from an acid bath and which are to be employed in this process, when dyed alone from an acid bath on such fiber material yield quite particularly non-uniform and very often completely useless dyeings. This is easily understandable since these dyestuffs are precipitated by the acid present in the dyebath in coarse form and in this condition cannot penetrate sufiiciently deeply into the material to be dyed; they are retained by the outermost fiber layers which act as a filter.
  • the dyestuffs remain in solution even in the acid medium or at least in such a fine state of division that the material to be dyed is no longer capable of acting as a filter and becomes uniformly dyed throughout.
  • the new process and the new preparations are accordingly of especial advantage for machine dyeing in which as a rule concentrated dyebaths are used and the material to be dyed is treated in relatively close form in the bath so that the filter efiect tends to be large.
  • machine dyeing are to be understood in this case those dyeing methods in which the material to be dyed remains stationary and the dyebath is caused to move, for example by means of a circulating pump.
  • those are of special advantage which contain ortho:ortho-dihydroxymonoazo dyestuffs which are suitableper se for dyeing according to the single bath chroming process but are not suitable for dyeing according to the after-chroming process on account of insufiicient solubility in the acid medium, and at the same time such ortho:ortho'-dihydroxymonoazo dyestuffs as are suitable both for dyeing according to the single bath chroming process and also for dyeing according to the after-chroming process;
  • a dye preparation is prepared by producing a uniform powder mixture from:
  • the dyestufis can also be dissolved consecutively in corresponding quantity proportion in about parts of water and the stock solution produced in this way employed according to the same directions, whereby practically the same resultisobtained.
  • the loose wool can also be dyed with 1.3 parts of the following mixture in. the same way, a level, reddish brown dyeing then likewise being obtained.
  • N02 OCHa 1 A process for dyeing woolwhich comprises conducting the dyeing from an acid bath with an ortho ortho -dihydroxymonoazo which per se is soluble in a dyebathhaVing a pH value greater than 6.3 and up to about 8 but which is practically insoluble 'in'a dyebath of which the pH valuelies substantially below 6.3, in the presence of an ortho:ortho'-dihyroxymonoazo dyestuff which per se is soluble in a dyebath having a pH value below 6.3.
  • a process for dyeing wool which comprises conducting dyeing from an acid bath with an ortho:ortho'-dihydroxymonoazo dyestuif which per se is soluble in a dyebathhaving a pH value greater than 6.3 and up to about 8 but which is practically insoluble in a dyebath of which the pH value lies substantially below 6.3, which dyestuff is free from sulfonic acid and carboxylic dyestuff .2) the dyestuffof the.
  • Formula .I isfreplaced 12 acid groups, contains-a single sulfomc acid amide group and corresponds to the formula wherein R1 stands foran aromatic radical of the benzene series in which the azo group and the hydroxyl group are in ortho-position to one another and R3 stands for a phenyl radical, in the presence of an ortho:ortho-dihydroxymonoazo dyestufl which per se is soluble in a dyebath having a pH value below 6.3.
  • a process for dyeing wool which comprises conducting dyeing from an acid bath with the dyestuif of the formula in the-presence of the dyestuif of the-formula N02 CHs 6.
  • a processfor dyeing wool which comprises conducting dyeing from an acid bath with the dyestuif of the formula in the presence of the dyestuif of the formula NO; CH3
  • a process for dyeing W001 which comprises conducting dyeing from an acid bath with the dyestuif of the formula andthe dyestuif of the formula.
  • a dyestuif preparation containing an ortho:ortho'-dihydroxymonoazo dyestulf which per se is soluble in a dyebath having a pH value greater than 6.3 and up to about 8 but which is practically insoluble in a dyebath of: which the pH value lies substantially below 6.3, which dyestufif is free from sulfonic acid and carboxylic acid groups, contains a single nitro group and corresponds to the formula 1 1-N N1 z wherein R1 and R2 each stand for an aromatic radical of the benzene series in which the azo group and the hydroxyl group are in ortho-position to one another, and an ortho:ortho'-dihydroxymonoazo dyestufi which per se is soluble in a dyebath having a pH value below 6.3.
  • a dyestuif preparation stuff of the formula containing the dye and the dyestuff of the formula I 14.
  • a dyestuif preparation containing the dyestufi of the formula (m OH 15 .theflyestufiofitheformula OZN N N eNHtCTOQHa I V l lo: $113 and the dyestufi of the formula R l x No; O-CB: V .15. .A;dyestufi preparationcontaining the dyestufi-lofthe formula v r s ozNHz 7 I v CH3 the dyestu'fi of the formula I no3s'-O-N:N-O
  • a dyebath having a pH value from 3 to 5 and containing an ortho:ortho-dihydroxymonoazo dyestufl? which per se is soluble in a dyebath having a pH value greater than 6.3, which dyestufi is free from sulfonic acid and carboxylic acid groups, contains a single sulfonic acid amide group and corresponds to the formula wherein R1 stands for an aromatic radical of thebenzene series in which the azo group and the hydroxyl group are in ortho-position to one another and R3 stands for a phenyl, radical, and an ortho ortho' dihydroxymonoazo dyestufi which per se is soluble in a 'dyebath having a pH value belo w.6.3.

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  • Textile Engineering (AREA)
  • Coloring (AREA)
US139794A 1949-02-11 1950-01-20 Dyeing processes for wool and preparations therefor Expired - Lifetime US2610103A (en)

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CH169328X 1949-02-11

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AT (1) AT169328B (de)
DK (1) DK78163C (de)
GB (1) GB671243A (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2729629A (en) * 1951-04-25 1956-01-03 Sandoz Ag Green substantive dyestuff mixtures and process of making same
US3285906A (en) * 1964-02-03 1966-11-15 Stange Co Monoazo pyrazole dyes

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2058433A (en) * 1932-10-15 1936-10-27 Chem Ind Basel Dyeing of acetate artificial silk
US2060186A (en) * 1932-10-15 1936-11-10 Soc Of Chemical Ind Dyeing of acetate artificial silk

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2058433A (en) * 1932-10-15 1936-10-27 Chem Ind Basel Dyeing of acetate artificial silk
US2060186A (en) * 1932-10-15 1936-11-10 Soc Of Chemical Ind Dyeing of acetate artificial silk

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2729629A (en) * 1951-04-25 1956-01-03 Sandoz Ag Green substantive dyestuff mixtures and process of making same
US3285906A (en) * 1964-02-03 1966-11-15 Stange Co Monoazo pyrazole dyes

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Publication number Publication date
AT169328B (de) 1951-11-10
GB671243A (en) 1952-04-30
DK78163C (da) 1954-09-27

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