US3687603A - Simultaneous dyeing of wool and cotton fibrous material with condensation product of formaldehyde and mixture of sulfones and hydroxybenzenesulfonic acids - Google Patents

Simultaneous dyeing of wool and cotton fibrous material with condensation product of formaldehyde and mixture of sulfones and hydroxybenzenesulfonic acids Download PDF

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Publication number
US3687603A
US3687603A US773326A US3687603DA US3687603A US 3687603 A US3687603 A US 3687603A US 773326 A US773326 A US 773326A US 3687603D A US3687603D A US 3687603DA US 3687603 A US3687603 A US 3687603A
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US
United States
Prior art keywords
wool
formaldehyde
mixture
fibrous material
dyeing
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
US773326A
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English (en)
Inventor
Heinz Abel
Melvin Harris
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
Original Assignee
Ciba Geigy AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Application granted granted Critical
Publication of US3687603A publication Critical patent/US3687603A/en
Anticipated expiration legal-status Critical
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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/44General 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
    • D06P1/52General 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 synthetic macromolecular substances
    • D06P1/56Condensation products or precondensation products prepared with aldehydes
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00Sulfones; Sulfoxides
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/82Textiles which contain different kinds of fibres
    • D06P3/8204Textiles which contain different kinds of fibres fibres of different chemical nature
    • D06P3/8219Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and amide groups
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/12Reserving parts of the material before dyeing or printing ; Locally decreasing dye affinity by chemical means
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02Material containing basic nitrogen
    • D06P3/04Material containing basic nitrogen containing amide groups
    • D06P3/14Wool
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02Material containing basic nitrogen
    • D06P3/04Material containing basic nitrogen containing amide groups
    • D06P3/14Wool
    • D06P3/16Wool using acid dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02Material containing basic nitrogen
    • D06P3/04Material containing basic nitrogen containing amide groups
    • D06P3/14Wool
    • D06P3/20Wool using mordant dyes using metallisable dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58Material containing hydroxyl groups
    • D06P3/60Natural or regenerated cellulose
    • D06P3/62Natural or regenerated cellulose using direct dyes
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916Natural fiber dyeing
    • Y10S8/917Wool or silk
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916Natural fiber dyeing
    • Y10S8/918Cellulose textile

Definitions

  • wool can be advantageously dyed with wool dyes and cellulosic fibres with substantive cotton dyes in one and the same bath, when dyeing is performed in baths that contain in addition to the dyestuffs fibreafiinic wool resisting agents and hexamethylenetetramine and which are of acid reaction at least at the start of the dyeing operation.
  • the wool resisting agent in the bath is a condensation product of formaldehyde and a mixture of (a) a sulphone containing two monocyclic benzene residues bound to the SO groups and further substituted by hydroxyl groups and (b) a monocyclic hydroxybenzenesulphonic acid.
  • wool is dyed simultaneously with cellulosic fibrous material.
  • Suitable cellulosic fibrous materials are regenerated cellulose, such as rayon or spun rayon, as well as native cellulose such as linen or especially cotton. These fibrous materials may be in different stages of their processing, for example loose or mixed yarns or in form of fabrics. They may be present in intimate mixtures, for example in mixed weaves, or the individual types of fibre may form large fibre combinations; this is the case, for example, in fabrics in which warp and weft consist of different types of material, or in carpets in which the pile and the backing are made from different materials. So-called half-wool is specially preferred; it consists of wool and cotton, and this mixture may be intimate or brought about only during the doubling or weaving operation.
  • the wool share is dyed with wool dyes which may belong to a variety of types, especially to the group of acid azo dyes or of the acid anthraquinone dyestufis.
  • the monoazo dyes are specially suitable.
  • Advantageous results have been obtained with chromium or cobalt complexes of monoazo dyes that contain more than ice one molecule of dyestnff for every atom of metal bound in complex union, and in which at least one dyestuif molecule is free from sulphonic acid groups and from carboxyl groups not participating in the complex formation.
  • the heavy metal atom may be bound with two different or two identical dyestuif molecules.
  • the complexforming group of the dyestuffs may be, for example, an orthcrhydroxy-ortho'-aminoazo grouping, an ortho-hydroxy-ortho'-carboxyazo grouping or preferably an ortho, ortho-dihydroxyazo grouping.
  • an orthcrhydroxy-ortho'-aminoazo grouping an ortho-hydroxy-ortho'-carboxyazo grouping or preferably an ortho, ortho-dihydroxyazo grouping.
  • the cellulose fibres are dyed with substantive cotton dyestuffs which advantageously have as such little affinity for the wool fibre. Otherwise, these dyestuffs may belong to a variety of types.
  • azo dyes especially disazo and polyazo dyes, which may contain metal bound in complex union, preferably copper, or azoxy dyestuffs or sulphonated copper phthalocyanines.
  • the condensation products to be used in the present process are prepared from mixtures of sulphones and sulphonic acids of the kind referred to above.
  • mixtures are used in which the molecular ratio of (a) sulphone to (b) sulphonic acid is from 40:60 to :15.
  • Both the sulphones and sulphonic acids suitable as relevant starting materials are known. From among the sulphones the dihydroxydiphenylsulphones of the formula Ha l- 0.
  • R and R independently of each other, represent hydrogen atoms or methyl or sulphonic acid groups.
  • R and R independently of each other, represent hydrogen atoms or methyl or sulphonic acid groups.
  • Suitable monocyclic hydroxybenzenesulphonic acids are, for example, phenolsulphonic acid such as 1-hydroxybenzene-4-sulphonic acid and cresolsulphonic acids sozn drox'ybenzene, such as phenol, p-cresol or a xylenol, with Manufacturing instruction concentrated sulphuric acid; then water is added and the alkaline reaction is adjusted by addition of the requisite A miXtl-lffi f 317 gof Y Y- ll p .quantity of alkali metal hydroxide, and without intery p and 150-5 E- y yy mediate separation the condensation with formaldehyde 5 slllphonic acid in 100 f Wat is endered alkaline i f d, with 463 g. of 30% aqueous sodium hydroxide solution.
  • the necessary acid reac- P 'f" 9 is reacted with form tion is advantageously adjusted by the addition of acetic aldehyde m the Indicated manner acid to the dyebath. Since hexamethylenetetramine con- Example tinuously gives off ammonia during dyeing, the pH value of the dyebath, and incidentally also of the wool, rises in course of time. However, with the quantities of acetic acid conventionally used in dyeing from acid baths it is quite possible to conduct the dyeing process so that even when dyeing takes a relatively long time the pH value never rises substantially above 7 so that it is possible to positively prevent any damage to the wool fibre caused by excess alkalinity.
  • condensation products prevent the substantive cotton dyestuffs from depositing on the wool.
  • dyeing half-wool it is endeavoured to achieve as even a tinctorial strength as possible for the two fibres; this is considerably facilitated in dyeing by the present process since the two fibres are (1) OH G A preparation is manufactured by mixing 1 part of the condensation product A with 2 parts of hexamethylenetetrarnine.
  • half-wool warp: viscose spun rayon; weft: pure wool boucle yarn
  • warp viscose spun rayon
  • weft pure wool boucle yarn
  • the present process has the advantage that, even when relatively small quantities of a readily accessible agent (b) dyestufl of the formula H033 C Ha 1103s NH Ho OCH:
  • the above- (b), the wool dyes shown in column I in combination with mentioned quantities of these substances may be admixed the appropriate substantive dyestuffs in column II of the to form stable preparations ready for use and suitable for following table may be used in the indicated manner for the performance of the present process.
  • the two constituents of the preparation may Instruction and in the example are by weight. be added at the same ratio singly to the dyebath.
  • sulfones (a) are of the formula in which R; and R independently of each other, represent a member selected from the group consisting of hydrogen atoms, methyl and sulfonic acid groups.
  • condensation products of the indicated kind contain (a) 4,4- dihydroxy 3 methyl-diphenylsulfonic-(1,1) and (b) 1-hydroxy-2-methylbenzene-4-sulfonic acid.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
US773326A 1967-11-08 1968-11-04 Simultaneous dyeing of wool and cotton fibrous material with condensation product of formaldehyde and mixture of sulfones and hydroxybenzenesulfonic acids Expired - Lifetime US3687603A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1562367A CH481263A (de) 1967-11-08 1967-11-08 Verfahren zum gleichzeitigen Färben von Wolle und cellulosehaltigem Textilfasermaterial und zur Durchführung des Verfahrens geeignete Präparate

Publications (1)

Publication Number Publication Date
US3687603A true US3687603A (en) 1972-08-29

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Family Applications (1)

Application Number Title Priority Date Filing Date
US773326A Expired - Lifetime US3687603A (en) 1967-11-08 1968-11-04 Simultaneous dyeing of wool and cotton fibrous material with condensation product of formaldehyde and mixture of sulfones and hydroxybenzenesulfonic acids

Country Status (6)

Country Link
US (1) US3687603A (enExample)
BE (1) BE723501A (enExample)
CH (1) CH481263A (enExample)
ES (1) ES359966A1 (enExample)
FR (1) FR1591243A (enExample)
GB (1) GB1226165A (enExample)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USB314489I5 (enExample) * 1971-12-21 1975-01-28 Ciba Geigy Ag
US3870682A (en) * 1970-10-29 1975-03-11 Minnesota Mining & Mfg Aldehyde condensation products of fluoraliphatic phenols
US3872056A (en) * 1974-01-14 1975-03-18 Ewald Daubach Manufacture of phenol/formaldehyde resins
US3931083A (en) * 1973-02-06 1976-01-06 Showa Denko Kabushiki Kaisha Water-reducing admixtures for ceramic pastes
US4218366A (en) * 1974-02-21 1980-08-19 Dainippon Pharmaceutical Co., Ltd. Condensation product of 4,4'-dihydroxydiphenyl sulfone, 4,4'-dihydroxydiphenylsulfone sulfonic acid and a lower aldehyde and method of preparation
US4800118A (en) * 1987-11-04 1989-01-24 West Point Pepperell Compositions and methods for imparting stain resistance to textile articles

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3870682A (en) * 1970-10-29 1975-03-11 Minnesota Mining & Mfg Aldehyde condensation products of fluoraliphatic phenols
USB314489I5 (enExample) * 1971-12-21 1975-01-28 Ciba Geigy Ag
US3925016A (en) * 1971-12-21 1975-12-09 Ciba Geigy Ag Polyarcrylonitrile basic dyeing process with anionic assistant
US3931083A (en) * 1973-02-06 1976-01-06 Showa Denko Kabushiki Kaisha Water-reducing admixtures for ceramic pastes
US3872056A (en) * 1974-01-14 1975-03-18 Ewald Daubach Manufacture of phenol/formaldehyde resins
US4218366A (en) * 1974-02-21 1980-08-19 Dainippon Pharmaceutical Co., Ltd. Condensation product of 4,4'-dihydroxydiphenyl sulfone, 4,4'-dihydroxydiphenylsulfone sulfonic acid and a lower aldehyde and method of preparation
US4800118A (en) * 1987-11-04 1989-01-24 West Point Pepperell Compositions and methods for imparting stain resistance to textile articles

Also Published As

Publication number Publication date
DE1805793B2 (de) 1976-09-09
FR1591243A (enExample) 1970-04-27
ES359966A1 (es) 1970-06-16
CH481263A (de) 1969-12-31
DE1805793A1 (de) 1969-06-26
BE723501A (enExample) 1969-05-07
CH1562367A4 (enExample) 1969-05-30
GB1226165A (enExample) 1971-03-24

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