US2989363A - Process for improving the dyeability of shaped structures of polyesters based on terephthalic acid - Google Patents

Process for improving the dyeability of shaped structures of polyesters based on terephthalic acid Download PDF

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Publication number
US2989363A
US2989363A US643947A US64394757A US2989363A US 2989363 A US2989363 A US 2989363A US 643947 A US643947 A US 643947A US 64394757 A US64394757 A US 64394757A US 2989363 A US2989363 A US 2989363A
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Prior art keywords
sulfur trioxide
dyeability
ether
solution
acid
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US643947A
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Hartmann Adolf
Happe Wilhelm
Gatys Gerhard
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Hoechst AG
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Hoechst AG
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
    • D06M11/51—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with sulfur, selenium, tellurium, polonium or compounds thereof
    • D06M11/55—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with sulfur, selenium, tellurium, polonium or compounds thereof with sulfur trioxide; with sulfuric acid or thiosulfuric acid or their salts
    • 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
    • D06P1/65106—Oxygen-containing compounds
    • D06P1/65143—Compounds containing acid anhydride or acid halide groups
    • 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
    • D06P1/673—Inorganic compounds
    • D06P1/67333—Salts or hydroxides
    • D06P1/6735—Salts or hydroxides of alkaline or alkaline-earth metals with anions different from those provided for in D06P1/67341
    • D06P1/67375—Salts or hydroxides of alkaline or alkaline-earth metals with anions different from those provided for in D06P1/67341 with sulfur-containing anions
    • 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
    • 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
    • Y10S8/04—Polyester fibers

Definitions

  • linear polyesters based on terephthalicacid and shaped structures thereof such as fibers, filaments: or foils, show a low absorptivity for dyestuffs present in the form of an aqueous solution or dispersion. It is known to improve the dyeability ofthe polyesters mentioned above as well as that of the goods produced thereof by treating the shaped articles of polyesters with vapours of sulfuric acid, sulfuric anhydride or chloro-sulfonic acid.
  • the shaped fibers, filaments or foils obtained according to this method exhibit however, considerable disadvantages.
  • the improvement in the dyeability reached by the known process is often unsatisfactory and insufiicient for many purposes.
  • the dyeings obtained in this way are more or less dull and not fast to rubbing. It is true that the depth of shade can be'improved, when the vapours mentioned above are caused to act upon the goods at an elevated temperature, for instance at 50 C.
  • the application of the elevated temperatures often gives rise to stained tints which are caused in the gaseous phase by the unequal heating of the material to be dyed.
  • halogen compounds of sulfur oxygen acids are, for instance, halogenated sulfonic acids such as chlorosulfonic acid and fluorosulfonic acid, sulfuryl chloride, pyro-sulfuryl chloride, thionyl chloride.
  • halogenated sulfonic acids such as chlorosulfonic acid and fluorosulfonic acid
  • sulfuryl chloride pyro-sulfuryl chloride
  • thionyl chloride sulfur trioxide
  • ethers for the formation of addition products there enter into consideration, for instance, aliphatic and cyclic ethers, such as B.[3'-dichloro-diethylether, tetrahydrofurane, dioxane and thioxane.
  • tertiary amines there may be mentioned, for instance, aliphatic amines, such as trimethyl-amine or triethyl-amine; aromatic amines, such as N.N-dimethyl-aniline; heterocyclic compounds, for instance pyridine.
  • the ethers offer the advantage of intensifying the reaction btates atent O whereby a particularly good dyeing activation is reached, the addition of tertiary amines causes a smoother but very uniform reaction which in the dyeing process results in particularly uniform and clear shades.
  • the amount of ethers or amines added generally corresponds to the molar proportions known for the addition products: For'example one or two mols of sulfur trioxide or chlorosulfonic acid being applied for one mol of ether or tertiary amine. It is, however, possible to add the ethers or amines in any other quantity, particularly in a higher amount than is necessary for forming the addition products.
  • carbon halides such as chloroform, trichloro-ethane, tetrachloro-ethane, methylene chloride and ethylene chloride being particularly suitable. Mixtures of these solvents can also be used.
  • the concentration of the solutions containing the addition products may vary in wide limits. In general, solutions of 0.01% to 1%, preferably of 0.05 to 0.5% strength, are used. When the reactive compounds are'used in admixture with each other the desired effect can be improved, if necessary. There are particularly favorable, for instance, mixtures of chlorosulfonic acid and sulfuryl chloride in a ratio of 1:1 or of chloro sulfonic acid and sulfur trioxide in a ratio of 1:2.
  • the shaped structures can be treated with the reaction solutions at the ordinary or at an elevated temperature; the period of action may vary within wide limits, for instance between 2 and 60 minutes.
  • a preferred method of operation consists in allowing the solutions to act upon the structures at the boiling temperature of the solvent and with reflux.
  • the structures treated in this way, particularly fibers and filaments, as regards appearance and textile properties were either not altered or only favorably, in comparison with the initial material. They can easily be dyed under the usual conditions with numerous basic dyestuffs, and particularly with dispersion dyestuffs, for instance with a red dyestutf mixture consisting of 50% of a dyestutf corresponding to the formula $113 0 O OrN N N and 50% of a red dyestuff corresponding to the formula ChzCHrOH CHHCHQOH 3 thraquinone and 15.5% of a dycstuff corresponding to the formula or with a black dyestufi of the following composition:
  • polyester material additionally with hydrazine solutions or with N-formyl compounds which still contain a reactive hydrogen atom.
  • Water will preferably be used as solvent. It is, however, also possible to apply other appropriate solvents, for instance aliphatic alcohols, such as methanol, ethanol or their mixtures with water.
  • the solutions act upon the material for about 2 to 5 minutes.
  • the period of time indicated above depends upon the concentration of the hydrazine.
  • a concentration of 1 to 2% referred to the bath will, in general, be suflicient.
  • the period of action must be prolonged.
  • N-formyl compounds there may be mentioned, for instance, formamide and its derivatives substituted by aliphatic, cyclo-aliphatic, araliphatic radicals, e.g. ethylformamide, cyclo-hexylformamide, benzyl-formamide, di- (N formyl)-ethylene-diamine, di(N-formyl)-hexamethylene-diamine.
  • aliphatic, cyclo-aliphatic, araliphatic radicals e.g. ethylformamide, cyclo-hexylformamide, benzyl-formamide, di- (N formyl)-ethylene-diamine, di(N-formyl)-hexamethylene-diamine.
  • araliphatic radicals e.g. ethylformamide, cyclo-hexylformamide, benzyl-formamide, di- (N formyl)-ethylene-diamine, di(
  • solvents those compounds are used as under the test conditions do not react with a formyl group, for instance aliphatic alcohols, such as methanol or ethanol, ketones, such as acetone, ethers, such as diethyl ether, esters, such as ethyl acetate, aliphatic or cycloaliphatic hydrocarbons, such as hexane, cyclo-hexane or mixtures, such as light gasoline, carbon halides, such as carbon tetrachloride, chloroform, methylene chloride or ethylene chloride.
  • solvent water is preferred in order to reduce the costs.
  • the further treatment is carried out at an elevated temperature, usually in the boiling solution.
  • concentration of the solutions may vary within wide limits; it depends on the chemical constitution of the formyl compounds, on the duration of the treatment, on the temperature applied and on the effect desired. Generally, the concentration will be chosen so high that the period of treatment is within the favorable range of a continuous manufacture.
  • aqueous solutions of 0.1 to 10% strength, preferably of 0.5 to 5% strength will be used. In this case a period of treatment amounting to 2 to 5 minutes will be sufficient when a temperature of about 98 to 100 C. is applied. With lower temperatures the period of treatment must be prolonged or the concentration must be increased.
  • Example 1 20 grams of a stretched staple fiber of polyethylene glycol terephthalate having a single titer of 3 deniers are treated for 6 minutes under reflux at the boiling temperature with a solution of 3 grams of chlorosulfonic acid and 2.4 grams of dioxane in 1000 cc. of ethylene ch1oride. The solution is then separated off, the fiber is centrifuged for a short time and washed with about 2 liters of water of 50 C. to which 0.5 gram-liter of a phenol-poly-glycol ether with 20 units of ethylene-oxide had been added. Finally, the fibers are rinsed with handwarm water and dried.
  • the resistance of the fiber is practically not reduced; it can be dyed deep shades by means of dispersion dyestuffs.
  • a dyestuff mixture consisting of 50% of a red dyestufi corresponding to the formula CHzCHzOH and 50% of a red dyestufi corresponding to the formula a dark red tint is obtained by dyeing the fiber for minutes at the boil with an amount of dyestutf amounting to 4% of the weight of the fiber. After dyeing the fiber is rinsed with warm water and dried. The dyed material is well resistant to rubbing and washing at the boil.
  • Example 2 1.35 grams of pyridine are added to 300 cc. of ethylene chloride, a solution of 2.0 grams of chlorosulfonic acid in 200 cc. of ethylene-chloride is then added thereto, while stirring. 10 grams of the staple fiber mentioned in Example 1 and consisting of polyethylene glycol terephthalate are introduced into this solution, and the whole is heated to boiling for 10 minutes. The fiber is then separated and washed as described in Example 1.
  • the dyeings obtained with dispersion dyestuffs are very uniform, the shades are extremely clear and brilliant.
  • Example 3 44 grams of dioxane and 40 grams of sulfur trioxide are added to 10 liters of dry ethylene-chloride. With this solution 200 grams of spinning cable of polyethyleneglycol terephthalate having a total titer of 75,000 deniers and a resistance to breaking of the single filament of 4.8 grams-denier are treated for 5 minutes at the temperature '5 of reflux. The cable is then squeezed E and :washed with water of 50 C. containingper liter 0.5 gram of a phenol-polyglycol ether obtained by reaction ofthe phenol with 20 mols of ethylene oxide. The cable is then thoroughly rinsed with warm water and dried.
  • the spinning cable shows an agreeable, soft feeling, the resistance of the single filament amounts to 4.3 grams/denier.
  • the cable canbe dyed deep brilliant shades with numerous dispersion dyestulfs, for instance with an amount of a dyestuff mixture of 46% of the weight of the fiber and consisting of 0% of a red dyestuff corresponding to the formula CHzCHgOH and 50% of a red dyestuff corresponding to the formula or with 4 to 6% of a dyestufi mixture consisting of OHg.CH2OH l CzHs CHr-CHgOH 20.0% of a condensation product from cresol, formaldehyde and sodium sulfite, which was further heated with B-naphtholic acid formaldehyde and sulfite,
  • the cable is to be dyed with this dyestutt-mixture for 1 /2 hours at the boiling temperature.
  • Example 4 50 grams of sulfur trioxide are dissolved in 300 cc. of dry ethylene chloride. While stirring at 20 C., a solution of 55.1 grams of dioxane in 533 cc. of ethylene chloride is added to the first-mentioned solution.
  • 680 cc. of the solution thus obtained are diluted with 4320 cc. of ethylene chloride, and 100 grams of staple fiber 3/100 of polyethylene glycol terephthalate are introduced into the solution. The whole is heated for 5 minutes under reflux, care being taken that the fiber is always covered by the solution. Decantation then takes place, the fiber is centrifuged and treated for three minutes at 98 C. with an aqueous hydrazine hydrate solution of 2% strength. The fiber is then centrifuged again, washed several times with water of 40 to 50 C. and dried.
  • the fiber obtained in this way can be dyed deep shade, with good fastness properties with several dispersion dye- 6 "stufls, for instance with the dyestufii fromamino-azobeuzene o-cresolor the dyestuflf of the'following formula NHz N NHI
  • Example 6 A fiber flock of polyethylene glycol terephthalate (single titer 3 den.) whose dyeability has been improved in the abovedescribed manner by treatment with an addition product of dioxane and sulfur trioxide is then further treated for 3 minutes at C. with an aqueous solution of 3% strength of N-formyl-cyclo-hexylamine. The flock is then rinsed with water and dried. It canbe easily dyed with dispersion dyestuffs, the dyeings possessing good resistance to heat and showing a good fastness to light.
  • Example 7 A spinning cable of polyethylene glycol terephthalate whose dyeability has been improved in the above-disclosed manner by treatment with an addition product of dioxane and sulfur trioxide is treated for 5 minutes at the temperature of reflux with a solution of 2% strength of ethyl formamide in ethylene chloride. The cable is dried in a stream of hot air and treated as described in Example 5. The fiber obtained is characterized by a very good dyeability with numerous dispersion dyestuffs. The dyeings are resistant to ironing and conform with the type of shade.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Coloring (AREA)
  • Artificial Filaments (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US643947A 1956-03-10 1957-03-05 Process for improving the dyeability of shaped structures of polyesters based on terephthalic acid Expired - Lifetime US2989363A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DEF19763A DE1006383B (de) 1956-03-10 1956-03-10 Verfahren zur Verbesserung der Anfaerbbarkeit von geformten Gebilden aus Polyestern auf Terephthalsaeurebasis
DEF19938A DE1014958B (de) 1956-03-10 1956-03-31 Verfahren zur Verbesserung der Anfaerbbarkeit von geformten Gebilden aus Polyestern auf Terephthalsaeurebasis
DEF21669A DE1031274B (de) 1956-03-10 1956-11-15 Verfahren zur Verbesserung der Anfaerbbarkeit von geformten Gebilden aus Polyestern auf Terephthalsaeurebasis

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US (1) US2989363A (en, 2012)
BE (1) BE555688A (en, 2012)
DE (3) DE1006383B (en, 2012)
FR (1) FR1172936A (en, 2012)
GB (1) GB855546A (en, 2012)
NL (1) NL96674C (en, 2012)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3207568A (en) * 1960-06-09 1965-09-21 Sandoz Ltd Azo and anthraquinone dye mixture, dyeing cellulose acetate and polyesters therewith and the product of such dyeing
US3211515A (en) * 1961-10-19 1965-10-12 Rhodiaceta Process for the treatment of articles consisting of synthetic polymers and products obtained thereby
US3617338A (en) * 1969-10-20 1971-11-02 Dow Chemical Co Method for producing a latent striated effect on plastic films

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ118976A (en, 2012) * 1955-06-30
DE1068008B (de) * 1958-02-26 1959-10-29 Kalk &. Co. Aktiengesellschaft, Wiesbaden-Biebrich Verfahren zur Erhöhung des Haftvermögens von Flächengebilden aus Polyterephthalsäureglykolestern
DE1132890B (de) * 1959-07-30 1962-07-12 Hoechst Ag Verfahren zur Verbesserung der Anfaerbbarkeit von Fasergebilden aus Polyestern der Terephthalsaeure mit 1, 4-Dihydroxymethyl-cyclohexan
US3253880A (en) * 1961-10-09 1966-05-31 Chemstrand Corp Sulfonation of acrylonitrile polymers with sulfur trioxide to increase dye receptivity
BE632939A (en, 2012) * 1962-08-08
US3460896A (en) * 1964-10-14 1969-08-12 Eastman Kodak Co Polyester fibers having improved hydrophilicity as a result of modification with phosphoric acid,phosphorous acid or perchloric acid
CN110924188B (zh) * 2019-12-06 2022-05-20 常熟市江南印染有限公司 涤纶织物前处理染色同浴短周期少水染色工艺

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB613817A (en) * 1945-06-07 1948-12-03 James Gordon Napier Drewitt Improvements in the production or treatment of cellulose derivative or synthetic resin materials
GB613818A (en) * 1945-06-07 1948-12-03 James Gordon Napier Drewitt Improvements in the treatment of textile and other materials having a basis of cellulose derivatives or synthetic resins
US2647104A (en) * 1951-07-30 1953-07-28 Du Pont Linear polyester composition
US2849458A (en) * 1957-04-01 1958-08-26 Du Pont Production of sulfonates
US2852554A (en) * 1956-07-12 1958-09-16 Du Pont Alpha-sulfopolyfluoromonocarboxylic acids and derivatives hydrolyzable thereto

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB697657A (en) * 1950-06-14 1953-09-30 Calico Printers Ass Ltd Improvements relating to the processing of highly polymeric linear polyester materials
GB697986A (en) * 1950-11-27 1953-10-07 Denys Nicol Marvin Improvements in dyeing polyester filaments, yarns and fabrics

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB613817A (en) * 1945-06-07 1948-12-03 James Gordon Napier Drewitt Improvements in the production or treatment of cellulose derivative or synthetic resin materials
GB613818A (en) * 1945-06-07 1948-12-03 James Gordon Napier Drewitt Improvements in the treatment of textile and other materials having a basis of cellulose derivatives or synthetic resins
US2647104A (en) * 1951-07-30 1953-07-28 Du Pont Linear polyester composition
US2852554A (en) * 1956-07-12 1958-09-16 Du Pont Alpha-sulfopolyfluoromonocarboxylic acids and derivatives hydrolyzable thereto
US2849458A (en) * 1957-04-01 1958-08-26 Du Pont Production of sulfonates

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3207568A (en) * 1960-06-09 1965-09-21 Sandoz Ltd Azo and anthraquinone dye mixture, dyeing cellulose acetate and polyesters therewith and the product of such dyeing
US3211515A (en) * 1961-10-19 1965-10-12 Rhodiaceta Process for the treatment of articles consisting of synthetic polymers and products obtained thereby
US3617338A (en) * 1969-10-20 1971-11-02 Dow Chemical Co Method for producing a latent striated effect on plastic films

Also Published As

Publication number Publication date
DE1014958B (de) 1957-09-05
DE1031274B (de) 1958-06-04
BE555688A (en, 2012) 1957-03-30
DE1006383B (de) 1957-04-18
NL96674C (en, 2012)
GB855546A (en) 1960-12-07
FR1172936A (fr) 1959-02-17

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