US3690815A - Dyeing assisted by aryl esters of aryl sulfonic acids - Google Patents

Dyeing assisted by aryl esters of aryl sulfonic acids Download PDF

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Publication number
US3690815A
US3690815A US130026A US3690815DA US3690815A US 3690815 A US3690815 A US 3690815A US 130026 A US130026 A US 130026A US 3690815D A US3690815D A US 3690815DA US 3690815 A US3690815 A US 3690815A
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US
United States
Prior art keywords
dyeing
aryl
carrier
carriers
assisted
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
US130026A
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English (en)
Inventor
Kurt A Dellian
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 Corp
Original Assignee
Ciba Geigy Corp
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
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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
    • D06P1/65168—Sulfur-containing compounds
    • 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
    • D06P3/36—Material containing ester groups using dispersed dyestuffs
    • 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
    • D06P3/40—Cellulose acetate
    • D06P3/46—Cellulose triacetate
    • D06P3/48—Cellulose triacetate using dispersed dyestuffs
    • 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
    • Y10S8/921—Cellulose ester or ether

Definitions

  • the present invention is directed to a dye carrier composition and the process employing such composition for dyeing and/or printing a hydrophobic textile material such as polyester or cellulose triacetate.
  • the coloring composition employs dyestuffs which are relatively insoluble in water and require an additional carrier.
  • the technique of this disclosure employs a carrier of the general formula R -(SO O)R wherein R and R are the same or different aryl radicals which may have lower alkyl or halogen compounds.
  • the carriers of the present disclosure are well known in the prior art used for a dilferent utility as for example plasticizers.
  • the prior art in treatment of hydrophobic synthetic fibers has employed elevated pressures with temperatures generally greater than 250 F.
  • the prior art also has turned to specific carrier components. These carriers aid in the penetration of the dye into the fiber by causing a swelling of the base fiber.
  • the prior art carriers for hydrophobic fibers may be classified as aliphatic, aromatic or aliphaticaromatic compounds and combinations thereof which are capable of swelling the fibrous material and thus facilitating the penetration of the dyestuif in the fiber.
  • carriers in dyeing techniques upon hydrophobic fiber allows satisfactory results at temperatures as low as ZOO-210 F. and allows the employment of unpressurized equipment.
  • Convention preferred prior art carriers include chlorinated hydrocarbons such as chlorinated hydrocarbons such as chlorinated benzene.
  • other carriers are various derivatives of benzene or of phenol as for example phenol, orthoor paraphenylphenol, benzyl alcohol, aromatic carbonic esters, or ethers and benzoic or salicyclic acid.
  • the prior art carriers in most instances have been generally satisfactory, these carriers may possess an undesirable degree of toxicity, may not be biodegradable and may, in certain situations, produce variations in shade or adversely effect fastness.
  • the arylsulfonic carriers in the present invention can be considered to be a non-pollutant material.
  • the esters of this disclosure may be considered to be essentially odorless, non-toxic and biodegradable. Due to these properties of the carrier, important advantages are realized. Solely because of their non-pollutant and biodegradable aspects, these carriers become more desirable than most prior art carriers. illustratively, from an environmental standpoint, the biodegradable characteristics provide breakdown bypassing contamination considerations.
  • the carriers disclosed herein function in the desirable manner in facilitating penetration of the dyestuff in the fiber.
  • the carrier in the dyebath permits an eificient drawing rate of the dyestutf and aids in permitting good fastness with uniform shade in the dyeing operation.
  • the dyestulfs to be employed upon the synthetic hydrophobic textiles with the carrier of this disclosure are disperse dyestulfs.
  • a disperse dyestulf refers to organic colored compounds which will be only at most slightly water-soluble.
  • these disperse dyestuffs are applied in the form of aqueous dispersions.
  • the types of dyestuffs employed are well known in the prior art and illustratively may be azo and aminoanthaquinone agents.
  • the hydrophobic textile materials that are dyed by the technique employing the disperse dyestuffs in a carrier include polyester and cellulose triacetate fibers.
  • Polyester fibers may be derived from high melting linear polyethyleneglycol terephthale and include Terylene, Dacron, Tergal, Diolen or Trevia while cellulose triacetate fibers include Arnel, Tricel and Courpleta.
  • a desirable class of aryl sulfonic esters are of the formula wherein replacement of hydrogen by up to three lower alkyl and/or halogen atoms may take place on each of the aryl groups. Desirably, the substitution in each group will be limited to one.
  • the carrier of the present invention is desirably employed in emulsified form since it is substantially water insoluble.
  • the manner of obtaining the emulsification is not critical and may take place in several ways such as premixing the ester with the emulsifier and emulsifying the dyebath.
  • the ester carrier can be dissolved in a solvent such as alcohol and then added to the dyebath which contains the emulsifier.
  • particularly useful emulsifiers are oxethylated sulfonates, alkyl aryl phenols or sulfates of higher fatty acids.
  • the arylsulfonic ester carriers of the present invention are stable compounds both under acid and alkaline conditions and they do not undergo decomposition during the dyeing and printing process.
  • the ester carriers possess advantages in that they are essentially odorless as well as possessing nontoxic and biodegradable properties.
  • the employed esters do not undersirably influence the light fastness in dyeing processes in contrast to other carriers such as o-phenyl-phenol.
  • disperse dyes are the Color Index C. I. Disperse dyes.
  • the concentration of the carrier utilized may vary with broad ranges and generally will be present between 1 to 15 percent by weight of the textile goods. Desirably, the carrier ester will be 2 to 8 percent by weight. This concentration of the carrier will be based in part, on the type of disperse dye, the substrate utilized and the technique of application as for example printing or dyeing.
  • EXAMPLE 1 A polyester fabric from polyethylene terephthalate is introduced into an aqueous dye bath with a liquor to fabric weight ratio of 30:1 which contains 3% by weight of the fabric of the following dyestulf:
  • an emulsion of the following composition 70 parts of phenyl benzenesulfonate, parts the sodium salt of sulfonated oleic acid amylester and 20 parts of water.
  • the dyebath is raised to boiling and kept 2 hours at this condition.
  • the fabric is then rinsed, and soaped.
  • An after treatment with 4 ml./l. caustic soda 38 percent Be and 5 g./l. sodium hydrosulfite at 80 C. for 20 minutes is utilized.
  • EXAMPLE 2 A polyethyleneterephthalate fabric is dyed in a liquor ratio of 40:1 in an aqueous dyebath containing 8% of an emulsion consisting of:
  • the dyebath is raised to boil and kept 90 min. at this temperature followed by rinsing and soaping. A deep yellow shade is obtained with good all round fastness.
  • Example 3 The materials and techniques of Example 1 were duplicated except the dyestufi was replaced by an equal weight of:
  • Example 4 The materials and techniques of Example 1 were duplicated except an 8% emulsion of a active ingredient based on 4-chloro-phenyl-4-chlorobenzene sulfonic ester was employed.
  • Example 5 The materials and techniques of Example 1 were duplicated except a mixture of 1% of each dyestuif of Examples 1 and 2 were employed. An orange shade of generally good fastness is obtained.
  • Example 6 The materials and techniques of Example 2 were employed except an 8% emulsion containing a 65% active ingredient based on 4-chloro phenyl benzene sulfonic acid ester was employed.
  • EXAMPLE 7 A polyethylenterephthalate fabric is printed with a print paste containing 20 g./kg. of the dyestulf used in Example 1. 50 g./kg. phenyl benzenesulfonic acid ester and a thicke'ner of starch ether-locust bean gum. The print is submitted to a 30 min. steaming. A fast red shade is obtained.
  • a process for coloring synthetic hydrophobic fibers with a disperse dyestuif in a carrier comprisles utilizing an arylsulfonic ester carrier of the formu a:
  • R (SO --O)--R wherein R and R are selected from the group of the same or different aryl radicals.
  • hydrophobic fiber is chosen from the group consisting of polyester and cellulose triacetate.
  • X and X represent lower alkyl or halogen and n and m represent a number from 0 to 3.
  • hydrophobic fiber is chosen from the group consisting of polyester and cellulose triacetate.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Coloring (AREA)
US130026A 1971-03-31 1971-03-31 Dyeing assisted by aryl esters of aryl sulfonic acids Expired - Lifetime US3690815A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US13002671A 1971-03-31 1971-03-31

Publications (1)

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US3690815A true US3690815A (en) 1972-09-12

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Application Number Title Priority Date Filing Date
US130026A Expired - Lifetime US3690815A (en) 1971-03-31 1971-03-31 Dyeing assisted by aryl esters of aryl sulfonic acids

Country Status (10)

Country Link
US (1) US3690815A (en, 2012)
AU (1) AU459520B2 (en, 2012)
CA (1) CA972502A (en, 2012)
CH (2) CH437272A4 (en, 2012)
DE (1) DE2215717A1 (en, 2012)
FR (1) FR2132264B1 (en, 2012)
GB (1) GB1358232A (en, 2012)
IT (1) IT952466B (en, 2012)
NL (1) NL7204384A (en, 2012)
ZA (1) ZA722205B (en, 2012)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3864077A (en) * 1971-09-02 1975-02-04 Bayer Ag Non-Aqueous Dyestuffs with a Phthalic Acid Dialkyl Ester
US3936268A (en) * 1974-11-07 1976-02-03 Diamond Shamrock Corporation Method of reducing barre in synthetic polymide textiles dyed with acid dyes
US5340489A (en) * 1992-06-05 1994-08-23 The Dow Chemical Company Aryl arenesulfonates and a method of lubrication using the aryl arenesulfonates
US8088850B1 (en) * 2007-05-30 2012-01-03 Henkel Corporation Polyacrylate compositions
US9243083B2 (en) 2008-04-03 2016-01-26 Henkel IP & Holding GmbH Thiol-ene cured oil-resistant polyacrylate sealants for in-place gasketing applications

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE742372C (de) * 1942-10-28 1945-01-12 Ig Farbenindustrie Ag Verfahren zum Faerben von geformten Gebilden aus Polyvinylchlorid, nachchloriertem Polyvinylchlorid oder Mischpolymerisaten aus Vinylchlorid und Vinylaethern oder -estern
FR1370475A (fr) * 1963-10-04 1964-08-21 Hoechst Ag Procédé de teinture de polymères contenant des groupes nitrile, en particulier des copolymères cyanure de vinylidène/acétate de vinyle

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3864077A (en) * 1971-09-02 1975-02-04 Bayer Ag Non-Aqueous Dyestuffs with a Phthalic Acid Dialkyl Ester
US3936268A (en) * 1974-11-07 1976-02-03 Diamond Shamrock Corporation Method of reducing barre in synthetic polymide textiles dyed with acid dyes
US5340489A (en) * 1992-06-05 1994-08-23 The Dow Chemical Company Aryl arenesulfonates and a method of lubrication using the aryl arenesulfonates
US8088850B1 (en) * 2007-05-30 2012-01-03 Henkel Corporation Polyacrylate compositions
US9243083B2 (en) 2008-04-03 2016-01-26 Henkel IP & Holding GmbH Thiol-ene cured oil-resistant polyacrylate sealants for in-place gasketing applications

Also Published As

Publication number Publication date
AU459520B2 (en) 1975-04-13
IT952466B (it) 1973-07-20
DE2215717A1 (de) 1972-10-12
GB1358232A (en) 1974-07-03
AU4049372A (en) 1973-10-04
FR2132264A1 (en, 2012) 1972-11-17
CA972502A (en) 1975-08-12
CH437272A4 (en, 2012) 1973-05-15
FR2132264B1 (en, 2012) 1975-03-21
CH541020A (de) 1973-05-15
ZA722205B (en) 1972-12-27
NL7204384A (en, 2012) 1972-10-03

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