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US3394984A - Iodination or hydroiodination of alkylene bisamide-containing polypropylene fibers dyd with basic dyes - Google Patents

Iodination or hydroiodination of alkylene bisamide-containing polypropylene fibers dyd with basic dyes Download PDF

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US3394984A
US3394984A US614518A US61451867A US3394984A US 3394984 A US3394984 A US 3394984A US 614518 A US614518 A US 614518A US 61451867 A US61451867 A US 61451867A US 3394984 A US3394984 A US 3394984A
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dyed
iodine
basic
light fastness
polypropylene fibers
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US614518A
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Koshimo Akio
Nara Hirohisa
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Nippon Rayon Co Ltd
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Nippon Rayon Co Ltd
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    • 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
    • D06P3/79—Polyolefins
    • D06P3/792—Polyolefins using basic dyes
    • 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
    • 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
    • D06P1/67316—Acids
    • 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
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/02—After-treatment
    • D06P5/10—After-treatment with compounds containing metal

Definitions

  • the present invention relates to a process for improving the light fastness of dyed polymeric olefines.
  • a process for improving the light fastness of dyed polymeric olefines comprises dyeing the polymeric olefines in a dye bath containing iodine or hydrogen iodide as an auxiliary agent.
  • a process for improving the light fastness of dyed polymeric olefines comprises after-treating the dyed polymeric olefines with iodine or hydrogen iodide.
  • iodine is used for improving the light fastness of dyed polymeric olefines which are dyed with basic, cation or acid dyestuffs.
  • the present invention is different from the prior method for the pre-treatment of polymeric olefines with iodine in that the object of the present invention is to improve the light fastness of the dyed product and the object of the prior method is to improve dyeability.
  • the synthetic fibres and other articles herein referred to as being formed of polymeric olefines included those produced of polyolefines alone, mixtures of polyolefines and other polymers, mixtures of polyolefines and organic compounds having lower molecular weight, graft polymers based on polyolefines, and copolymers of polyolefines with other compounds.
  • Treatments with other halogens and halogenides except iodine and hydrogen iodide give little effect to improve the light fastness of polymeric olefines dyed with basic and cation dyestuffs. Further, treatments with other compounds which are known as lightproof agents such as benzophenone, benztriazol and their derivatives give also no effect to improve the light fastness of polymeric olefines dyed with basic, cation or acid dyestuffs.
  • iodine or hydrogen iodide in said fibres or other articles absorbs energy of sunlight and prevent the decomposition of basic, cation dyestuffs, etc.
  • iodine or hydrogen iodide is used as an auxiliary agent during dyeing process in the present invention
  • synthetic fibres or other articles based on polymeric olefines are dyed in a bath containing requisite amounts of basic dyestuff and 05-15 of iodine based on the weight of fibres.
  • iodine is previously dissolved with a suitable solvent, and then added to the dye bath.
  • Dyeing is carried out at a given pH and 100 C. for 0.5-2 hours, and the dyed polymeric olefines obtained have very excellent light fastness.
  • dyed polymeric olefines are subjected to the after-treatment with iodine or hydrogen iodide in the present invention
  • synthetic fibres or other articles formed of polymeric olefines dyed with basic or cation dyestuffs are treated in the bath, in which iodine or hydrogen iodide is dissolved in water, alcohol, chloro form or an aqueous solution of potassium iodide, at a temperature higher than room temperature for from several minutes to 2 hours and then rinsed sufliciently. Further, this treatment can be carried out in iodine or hydrogen iodide vapour.
  • the present invention can be applied in case the polymeric olefines are dyed with basic, cation or acid dyestuffs after chemical treatment, such as chlorination, sulfonation and acid and amine treatments.
  • the light fastness of dyed polymeric olefines subjected to the after-treatment is outstandingly superior into that of the untreated products.
  • the light fastness of polymeric olefines dyed with basic dyestuffs is only grade 1 according to AATCC test when untreated, it becomes grade 4, 5, 6 or higher after being treated in accordance with one of the processes described above.
  • EXAMPLE 1 Crystalline polypropylene material having an average molecular weight of 77,000 was blended with 3% by weight of octadecylamine and methylene bis-stearamide respectively and subsequently drawn at a draw ratio of 5 after being melt-spun at 240 C.
  • the resulting fibre was treated with a bath of 20% hydrochloric acid solution at 100 C. for 30 min., neutralized with sodium carbonate solution and then rinsed with cold water sufficiently.
  • the fibre, thus treated was dyed in a weak alkaline bath containing the basic or cation dyestuffs described in Table I -at 100 C. for 60 min.
  • the light fastness of the dyed materials after the above treatment with iodine was greatly improved in comparison with untreated materials as shown in Table I.
  • the light fastness values in Table I are estimated by AATCC test using a Fade-Ometer.
  • the fibre thus obtained was dyed in a weak alkaline bath containing 5% (based on the weight of fibre) of iodine dissolved in g./l. of potassium iodide solution and basic and cation dyestuffs described in Table II at 100 C. for 60 min.
  • the light fastness of the materials thus dyed was greatly improved in comparison with materials dyed without the addition of iodine to the dye bath as shown in Table II.
  • the light fastness values in Table II are estimated by AATCC test using a Fade-Ometer.
  • EXAMPLE 3 After being treated with solution containing calcium hypochlorite and hydrochloric acid, polypropylene fibre was dyed in a weak alkaline bath containing basic or cation dyestuffs, as shown in Table III. The dyed material was subsequently treated in an aqueous solution of 5% of iodine (based on the weight of the fibres) and of potassium iodide (based on the weight of the fibres) at 90 C. for min., rinsed sufficiently and soaped.
  • iodine based on the weight of the fibres
  • potassium iodide based on the weight of the fibres
  • the light fastness of the dyed materials after being treated as described above, was greatly improved in comparison with untreated dyed materials as shown in Table III.
  • the light fastness values in Table III are estimated by AATCC test using a Fade-Ometer.
  • a process for improving the light fastness of polypropylene fibers blended with an alkylene bis-fatty acid amide dyed with a basic dyestufi which comprises treating said fibers with an aqueous solution containing 0.5- 15% of iodine or hydrogen iodide.
  • Diserens Chemical Technology of Dyeing and Printing, vol. 2, page 84, pub. 1951 by Reinhold Pub. Corp, N.Y.C. TP893D49.
  • Venkataramann The Chemistry of Synthetic Dyes, vol. I, page 69, pub. 1952 by Academic Press Inc., N.Y.C. TP913V4C2.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Coloring (AREA)

Description

United States Patent 3,394,984 IODINATIUN 0R HYDROIODINATION 0F ALKYL- ENE BISAMHDE-CONTAININ G POLYPROPYLENE FIBERS DYED WITH BASIC DYES Alrio Koshimo and Hirohisa Nara, Uji-shi, Kyoto-tn,
Japan, assignors to Nippon Rayon Co., Ltd., Kyotofu, Japan No Drawing. Continuation of application Ser. No. 251,487, Jan. 15, 1963. This application Feb. 7, 1967, Ser. No. 614,518
6 Claims. (Cl. 8-31) The present application is a continuation of S.N. 251,- 487, filed Jan. 15, 1963, now abandoned.
The present invention relates to a process for improving the light fastness of dyed polymeric olefines.
In general, brilliant shades are obtained by basic and cation dyestuffs, but the light fastness of the dyed products is not satisfactory. Accordingly, when above dyestuffs are used, dyed synthetic fibres and other articles formed of polymeric olefines possess extremely low light fastness, so that these dyestuffs cannot be used in practice.
As the result of extensive investigations to improve the light fastness of polymeric olefines which are dyed with basic and cation dyestuffs and to bring these dyed polymeric olefines into practical use, it has now been found that the addition of iodine into a dyebath or the aftertreatment of dyed polymeric olefines with iodine or with hydrogen iodide provides a marked improvement in the light fastness of polymeric olefines which are dyed with above dyestuffs and also acid dyestuffs.
According to the feature of the present invention, a process for improving the light fastness of dyed polymeric olefines comprises dyeing the polymeric olefines in a dye bath containing iodine or hydrogen iodide as an auxiliary agent.
According to the another feature of the present invention, therefore, a process for improving the light fastness of dyed polymeric olefines comprises after-treating the dyed polymeric olefines with iodine or hydrogen iodide.
The method for improving the dyeing properties of polyolefine fibres by treating them with iodine is known, but in the present invention iodine is used for improving the light fastness of dyed polymeric olefines which are dyed with basic, cation or acid dyestuffs.
Consequently, the present invention is different from the prior method for the pre-treatment of polymeric olefines with iodine in that the object of the present invention is to improve the light fastness of the dyed product and the object of the prior method is to improve dyeability.
The synthetic fibres and other articles herein referred to as being formed of polymeric olefines included those produced of polyolefines alone, mixtures of polyolefines and other polymers, mixtures of polyolefines and organic compounds having lower molecular weight, graft polymers based on polyolefines, and copolymers of polyolefines with other compounds.
Treatments with other halogens and halogenides except iodine and hydrogen iodide give little effect to improve the light fastness of polymeric olefines dyed with basic and cation dyestuffs. Further, treatments with other compounds which are known as lightproof agents such as benzophenone, benztriazol and their derivatives give also no effect to improve the light fastness of polymeric olefines dyed with basic, cation or acid dyestuffs.
Although the mechanism how the light fastness of dyed polymeric olefines treated with iodine or hydrogen iodide is improved is not clear, it may be considered that iodine or hydrogen iodide in said fibres or other articles absorbs energy of sunlight and prevent the decomposition of basic, cation dyestuffs, etc.
ice
In case iodine or hydrogen iodide is used as an auxiliary agent during dyeing process in the present invention, for example, synthetic fibres or other articles based on polymeric olefines are dyed in a bath containing requisite amounts of basic dyestuff and 05-15 of iodine based on the weight of fibres. In this case, iodine is previously dissolved with a suitable solvent, and then added to the dye bath. Dyeing is carried out at a given pH and 100 C. for 0.5-2 hours, and the dyed polymeric olefines obtained have very excellent light fastness.
In case dyed polymeric olefines are subjected to the after-treatment with iodine or hydrogen iodide in the present invention, for example, synthetic fibres or other articles formed of polymeric olefines dyed with basic or cation dyestuffs are treated in the bath, in which iodine or hydrogen iodide is dissolved in water, alcohol, chloro form or an aqueous solution of potassium iodide, at a temperature higher than room temperature for from several minutes to 2 hours and then rinsed sufliciently. Further, this treatment can be carried out in iodine or hydrogen iodide vapour.
The present invention can be applied in case the polymeric olefines are dyed with basic, cation or acid dyestuffs after chemical treatment, such as chlorination, sulfonation and acid and amine treatments.
The light fastness of dyed polymeric olefines subjected to the after-treatment is outstandingly superior into that of the untreated products. For example, if the light fastness of polymeric olefines dyed with basic dyestuffs is only grade 1 according to AATCC test when untreated, it becomes grade 4, 5, 6 or higher after being treated in accordance with one of the processes described above.
The following examples serve to illustrate the present invention, but they are not intended to limit it thereto.
EXAMPLE 1 Crystalline polypropylene material having an average molecular weight of 77,000 was blended with 3% by weight of octadecylamine and methylene bis-stearamide respectively and subsequently drawn at a draw ratio of 5 after being melt-spun at 240 C. The resulting fibre was treated with a bath of 20% hydrochloric acid solution at 100 C. for 30 min., neutralized with sodium carbonate solution and then rinsed with cold water sufficiently. The fibre, thus treated, was dyed in a weak alkaline bath containing the basic or cation dyestuffs described in Table I -at 100 C. for 60 min. After being treated in a bath containing 5% (based on the weight of fibres) of iodine dissolved in 10 g./l. aqueous potassium iodide solution at C. for 30 min., the dyed materials were rinsed sufficiently and then soaped.
The light fastness of the dyed materials after the above treatment with iodine was greatly improved in comparison with untreated materials as shown in Table I. The light fastness values in Table I are estimated by AATCC test using a Fade-Ometer.
TABLE I Light fastness Light of dyed fastness Dyestulls materials of dyed treated materials with untreated iodine (class) (class) Auromine (0.1. Basic Yellow 2) 0.1. 41,000. 4 1 Astra Phloxine FF cone. (0.1. Basic Red 12) 0.1. 48,070 5 1 Malachite Green (0.1. Basic Green 4) 0.1.
4,200 4 1 Victoria Pure Blue BOH (0.1. Basic Blue 7) 0.1. 42,595 4 1 Crystal Violet (0.1. Basic Violet 3) 0.1. 42,555- 5 2 Astrazon Yellow GRL 5 2 Asrpzon Orange R (0.1. Basic Orange 22) 4 1 Astrazon Black M 5 1 3 EXAMPLE 2 Crystalline polypropylene material having an average molecular weight of 77,000 was blended with by weight of polyetherester resin prepared from mixture of hydroxy benzoic acid, dimethyl terephthalate and ethylene glycol, and subsequently drawn at a draw ratio of 5, after being melt spun at 270 C.
The fibre thus obtained was dyed in a weak alkaline bath containing 5% (based on the weight of fibre) of iodine dissolved in g./l. of potassium iodide solution and basic and cation dyestuffs described in Table II at 100 C. for 60 min.
The light fastness of the materials thus dyed was greatly improved in comparison with materials dyed without the addition of iodine to the dye bath as shown in Table II. The light fastness values in Table II are estimated by AATCC test using a Fade-Ometer.
EXAMPLE 3 After being treated with solution containing calcium hypochlorite and hydrochloric acid, polypropylene fibre was dyed in a weak alkaline bath containing basic or cation dyestuffs, as shown in Table III. The dyed material was subsequently treated in an aqueous solution of 5% of iodine (based on the weight of the fibres) and of potassium iodide (based on the weight of the fibres) at 90 C. for min., rinsed sufficiently and soaped.
The light fastness of the dyed materials, after being treated as described above, was greatly improved in comparison with untreated dyed materials as shown in Table III. The light fastness values in Table III are estimated by AATCC test using a Fade-Ometer.
What is claimed is: i
1. A process for improving the light fastness of polypropylene fibers blended with an alkylene bis-fatty acid amide dyed with a basic dyestufi which comprises treating said fibers with an aqueous solution containing 0.5- 15% of iodine or hydrogen iodide.
2. A process according to claim 1, in which said polypropylene fibers are treated with said solution during dyeing with the basic dyestuff.
3. A process according to claim 1, in which said polypropylene fibers are treated with said solution after dyeing with the basic dyestutf.
4. A process according to claim 1, further comprising treating said polypropylene fibers with an aqueous solution of potassium iodide during application of said iodine or hydrogen iodide solution.
5. A process according to claim 4, in which the concentration of potassium iodide in said aqueous solution is 10 grams per liter.
6. A process according to claim 1, in which, when said member of said group is iodine, the concentration thereof in said solution is from 05-15% based on weight of polypropylene fibers.
References Cited UNITED STATES PATENTS 2,276,951 5/1942 Fisher 205163 2,537,627 1/1951 Weissart et a1. 260-457 2,805,960 9/ 1957 Wolinski 117--38 2,931,296 4/1960 Ryan et al. 8-100 FOREIGN PATENTS 1,083,651 6/1960 Germany.
OTHER REFERENCES Meili: American Dyestuff Reporter, May 1948, pages 81-83,TP890 512.
Diserens: Chemical Technology of Dyeing and Printing, vol. 2, page 84, pub. 1951 by Reinhold Pub. Corp, N.Y.C. TP893D49.
Venkataramann: The Chemistry of Synthetic Dyes, vol. I, page 69, pub. 1952 by Academic Press Inc., N.Y.C. TP913V4C2.
Finch: Fibers and Plastics, January 1960, pages 14-16.
Musgrave: Fibers and Plastics, August 1960, pages 241244.
Strobel et al.: American Dyestulf Reporter, Aug. 7, 1961, pages 583-585.
NORMAN G. TORCHIN, Primaly Examiner.
DONALD LEVY, Assistant Examiner.

Claims (1)

1. A PROCESS FOR IMPROVING THE LIGHT FASTNESS OF POLYPROPYLENE FIBERS BLENDED WITH AN ALKYLENE BIS-FATTY ACID AMIDE DYED WITH A BASIC DYESTUFF WHICH COMPRISES TREATING SAID FIBERS WITH AN AQUEOUS SOLTUTION CONTAINING 0.515% OF IODINE OR HYDROGEN IODIDE.
US614518A 1962-02-22 1967-02-07 Iodination or hydroiodination of alkylene bisamide-containing polypropylene fibers dyd with basic dyes Expired - Lifetime US3394984A (en)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2276951A (en) * 1939-02-25 1942-03-17 Standard Oil Dev Co Chlorinated polyisobutylene and process of making the same
US2537627A (en) * 1948-12-07 1951-01-09 Firestone Tire & Rubber Co Stabilization of chlorinated rubbery polymers
US2805960A (en) * 1952-11-29 1957-09-10 Du Pont Process for treating polyethylene structures and articles resulting therefrom
US2931296A (en) * 1954-05-21 1960-04-05 Polaroid Corp Processing of molecularly oriented sheets of transparent, linear, high molecular weight, hydroxyl-containing polymers to improve the dyeing qualities thereof
DE1083651B (en) * 1957-09-28 1960-06-15 Erwin Kaesemann Filter for the separation of spectral lines in the wave range from 240 to 260 mª–

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2276951A (en) * 1939-02-25 1942-03-17 Standard Oil Dev Co Chlorinated polyisobutylene and process of making the same
US2537627A (en) * 1948-12-07 1951-01-09 Firestone Tire & Rubber Co Stabilization of chlorinated rubbery polymers
US2805960A (en) * 1952-11-29 1957-09-10 Du Pont Process for treating polyethylene structures and articles resulting therefrom
US2931296A (en) * 1954-05-21 1960-04-05 Polaroid Corp Processing of molecularly oriented sheets of transparent, linear, high molecular weight, hydroxyl-containing polymers to improve the dyeing qualities thereof
DE1083651B (en) * 1957-09-28 1960-06-15 Erwin Kaesemann Filter for the separation of spectral lines in the wave range from 240 to 260 mª–

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