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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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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dyeing
aryl
carrier
carriers
assisted
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US130026A
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Kurt A Dellian
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Novartis Corp
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Ciba Geigy Corp
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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)

Abstract

A TECHNIQUE IS DISCLOSED FOR COLORING HYDROPHOBIC TEXTILE FIBERS WITH A DISPERSE, ESSENTIALLY WATER INSOLUBLE, DYESTUFF IN COMBINATION WITH AN ARYLSULFONIC ESTER CARRIER.

Description

Patented Sept. 12, 1972 Int. Cl. D061) 5/04 US. Cl. 8-173 9 Claims ABSTRACT OF THE DISCLOSURE A technique is disclosed for coloring hydrophobic textile fibers with a disperse, essentially water insoluble, dyestulf in combination with an arylsulfonic ester carrier.
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.
In the dyeing or printing of textile fibers wherein an organic dyestutt of negligible water solubility is employed, the prior art in treatment of hydrophobic synthetic fibers has employed elevated pressures with temperatures generally greater than 250 F. To bypass these costly and complex dyeing techniques, 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.
The use of 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. Additionally, 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.
While 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. In contrast to most prior art carriers, 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.
Yet 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. As employed herein, a disperse dyestulf refers to organic colored compounds which will be only at most slightly water-soluble. Generally, 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.
To replace the carrier of the prior art arylsulfonic esters of the formula 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. Alternatively the ester carrier can be dissolved in a solvent such as alcohol and then added to the dyebath which contains the emulsifier. Examples of 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. As previously mentioned, 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.
The specific dyes as well as the techniques of dyeing and printing are well known in the art. As illustrative of suitable 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.
In the dyeing and printing composition, well known conventional constituents may be employed such as thickeners, antifoaming agents, conventional carriers, etc. While the ester of the present disclosure is essential, other conventional carrier materials may additionally be utilized.
To further illustrate the innovative technique of the present invention, the following examples are provided.
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:
The syntheses of this dye is shown on pp. 432 and 433 of Venkataramann, supra.
Additionally 8% of an emulsion of the following composition is utilized: 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.
A deep red shade of generally very good fastness is obtained.
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:
(1) 65% of phenyl-4-chlorobenzenesulfonic ester (2) of the ammonium salt of oxethylated nonyl phenol sulfate and (3) water A dyestuff in an amount of 2.5% by weight of the following formula is added:
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:
The syntheses of this dye is shown 1n Venkataramann,
pages 391 and 392, The Chemistry of Synthetic Dyes, vol. III, pub. 1970 by Academic Press.
4 A reddish blue shade is obtained.
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.
What is claimed is:
1. A process for coloring synthetic hydrophobic fibers with a disperse dyestuif in a carrier which process 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.
2. The process of claim 1 wherein said aryl radicals comprise phenyl or naphthyl.
3. The process of claim 1 wherein said aryl radicals have constituents on at least one radical chosen from the group consisting of lower alkyl or halogen.
4. The process of claim 1 wherein the phenyl or naphthyl radical have constituents chosen from the group consisting of lower alkyl or halogen.
5. The process of claim 1 wherein said hydrophobic fiber is chosen from the group consisting of polyester and cellulose triacetate.
6. The process of claim 5 wherein said hydrophobic fiber is cellulose triacetate.
7. The process of claim 1 wherein said arylsulfonic ester is of the formula:
wherein X and X represent lower alkyl or halogen and n and m represent a number from 0 to 3.
8. The process of claim 7 wherein said hydrophobic fiber is chosen from the group consisting of polyester and cellulose triacetate.
9. The process of claim 8 wherein said hydrophobic fiber is cellulose triacetate.
References Cited UNITED STATES PATENTS 2,613,195 10/1952 Craig 264-78X DONALD LEVY, Primary Examiner
US130026A 1971-03-31 1971-03-31 Dyeing assisted by aryl esters of aryl sulfonic acids Expired - Lifetime US3690815A (en)

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AU (1) AU459520B2 (en)
CA (1) CA972502A (en)
CH (2) CH541020A (en)
DE (1) DE2215717A1 (en)
FR (1) FR2132264B1 (en)
GB (1) GB1358232A (en)
IT (1) IT952466B (en)
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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 (en) * 1942-10-28 1945-01-12 Ig Farbenindustrie Ag Process for dyeing molded structures made of polyvinyl chloride, post-chlorinated polyvinyl chloride or copolymers of vinyl chloride and vinyl ethers or esters
FR1370475A (en) * 1963-10-04 1964-08-21 Hoechst Ag Process for dyeing polymers containing nitrile groups, in particular vinylidene cyanide / vinyl acetate copolymers

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

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

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