US3700399A - Method of dyeing textile fibers with an anionic dyestuff in the presence of a quaternary ammonium salt - Google Patents

Method of dyeing textile fibers with an anionic dyestuff in the presence of a quaternary ammonium salt Download PDF

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Publication number
US3700399A
US3700399A US28121A US3700399DA US3700399A US 3700399 A US3700399 A US 3700399A US 28121 A US28121 A US 28121A US 3700399D A US3700399D A US 3700399DA US 3700399 A US3700399 A US 3700399A
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dye
fiber
dyeing
fibers
ammonium salt
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US28121A
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English (en)
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Shiro Shimauchi
Yuko Kitamura
Osamu Iwabuchi
Takeshi Matsui
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Teijin Ltd
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Teijin Ltd
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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
    • D06P1/655—Compounds containing ammonium groups
    • D06P1/66—Compounds containing ammonium groups containing quaternary ammonium groups

Definitions

  • X halogen or lower alkyl sulfonic acid residue.
  • the instant invention is directed to a method of dyeing polyvinyl chloride, polyacrylonitrile, modified polyester or cellulose acetate fibers with anionic dyestuffs.
  • the instant invention is directed to a method of dye ing the above-noted fibers with anionic dyestuffs in the presence of at least one compound having the general wherein R and R are groups selected from the class consisting of lower alkyl and lower allyl substituents having from about 1 to about 4 carbon atoms, Z is selected from the class consisting of benzyl, naphthyl, substituted benzyl, substituted naphthyl substituents, A is selected from the class consisting of butyl, phenyl and substituted phenyl substituents and X is selected from the group consisting of halogen atoms and lower alkyl sulfonic acid residues.
  • a primary object of the instant invention is to provide a dyeing method by which fibers may be fully dyed to a satisfactorily deep shade.
  • Yet another object of the instant invention is to provide a dyeing technique by which polyvinyl chloride fibers may be satisfactorily dyed to a deep shade.
  • a still further object of the instant invention is to provide a dyeing technique whereby numerous other textile materials may be satisfactorily dyed to a relatively deep shade.
  • Polyacrylonitrile fiber is normally dyed with cationic dyestuffs.
  • cationic dyestuffs when such cationic dyestuffs are employed and, further, when one desires to expand the colors which may be utilized, and, further, eliminate the difficulties in dyeing of mixed spun products.
  • acid dye is gen'erally considered preferable. Therefore, a still further object of the instant invention is to provide a dyeing process which easily facilitates the expansion of colors which may be dyed in connection with polyacrylonitrile fiber and mixed spun products.
  • a still further object of the instant invention is to provide a dyeing process which is particularly well suited for use in connection with mixed spun products in which one of the fibers is wool.
  • Polyester fiber has conventionally been dyed by the use of dispersed and/or azoic dyestuffs.
  • polyester fiber which has been so treated has not been found to be completely satisfactory inasmuch as the dyestuffs employed and the reaction of said dyestuff with the polyester fiber does not result in a dyed substrate having a desired degree of brightness. That is to say, that when such dispersed and/ or azoic dyestuffs were employed the brightness of the dyeings was inferior to that of an acetate fiber dyed with a dispersed dye, a nylon fiber dyed with acid dyes, and/or acrylic fiber dyed with a cationic dye.
  • polyester fiber dyed with dispersed and azoic dyestuffs were also unsatisfactory in connection with its color fastness to sublimation.
  • acid dyes which is made possible by the introduction of active sites for the acid dyestuffs into the fiber material.
  • Such techniques have, however, been unsuccessful to date. It is, therefore, a further object of the instant invention to provide a dyeing technique by which one can dye modified polyester fibers in bright shades and, further, which technique also provides a dyeing which has improved color fastness to sublimation.
  • Cellulose acetate fiber has also been dyed with dispersed dyestuffs in a manner similar to that employed with polyester fibers described above. It is noted, however, that there are numerous drawbacks associated with such dyeings such as a lack of brightness in the dyed product and the like. Therefore, a still further object of the instant invention is to provide a dyeing technique which is useful in connection with cellulosic acetate fiber which technique may be utilized to provide extremely bright shades and, further, to facilitate the dyeing of such fibers.
  • R and R are groups selected from the class consisting of lower alkyl group and lower allyl group, having l-4 carbon atoms.
  • Z is a group selected from the class consisting of benzyl group and naphthyl group, Z may have a substituent, A is a group selected from the class consisting of butyl group and phenyl group, said phenyl 3 group may have a substituent, and
  • X is selected from the group consisting of halogen atom and lower alkyl sulfonic acid residue.
  • One such method comprises making a substantially water insoluble complex by conjoint use of a cationic surfactant with an anionic dyestutf such as acid dyes or direct dyestuffs so as to effect the dye adsorption.
  • a cationic surfactant such as acid dyes or direct dyestuffs
  • Such techniques have not been suitable to produce satisfactory dyeings especially when applied to polyvinyl chloride, polyacrylonitrile, modified polyester and cellulose acetate fibers, i.e., the fibers subject to the process of the instant invention, even though said fibers are similarly hydrophobic. It has, therefore, quite unexpectedly been found that the abovenoted fibers may be dyed by the process of the instant invention wherein an anionic dyestuff is employed in combination with the above-noted compounds so as to effect the dyeing of said fibers.
  • the process of the instant invention comprises the conjoint use of the compound represented by Formula I in combination with an anionic dyestuff. It has been found that by use of such compounds it is possible to dye fibers which have hitherto been undyeable and/ or which have been scarcely dyeable by anionic dyestuffs.
  • the water-soluble or water-dispersible dye forms a complex with the aforesaid compound to become less insoluble in water and at the same time before compatible with and have afiinity for the hydrophobic fiber, with the consequence that this compound diffuses into the interior of the fiber owing to the elevated temperature and, at times, the action of the carrier to effect the adsorption of the dye.
  • the balance between the size of the complex of the dye and the compound and its compatibility and afiinity relative of the hydrophobic fiber becomes an important factor in determining the amount of dye adsorption.
  • the intended results cannot be obtained only by making dyes water insoluble.
  • the intended results can be only obtained when the specific compounds as prescribed by this invention are used.
  • Exemplary of the compounds represented by Formula I are the following:
  • said compounds may also contain a substituted phenyl, benzyl or naphthyl group wherein said grouping is substituted by an alkyl such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and the like, an alkoxy substituent such as methoxy, ethoxy, propoxy, butoxyx and the like, a halogen substituent such as chlorine, bromine, iodine and the like or numerous other substituents.
  • an alkyl such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and the like
  • an alkoxy substituent such as methoxy, ethoxy, propoxy, butoxyx and the like
  • a halogen substituent such as chlorine, bromine, iodine and the like or numerous other substituents.
  • a butyldialkylbenzyl ammonium salt or a trinaphthyl ammonium salt When dyeing polyvinyl chloride fiber it is noted that prefarbly one employs a butyldialkylbenzyl ammonium salt or a trinaphthyl ammonium salt. More specifically, the preferred salts for use in connection with polyvinyl chloride are the tri-n-butylbenzyl ammonium salt or the tributyl-2,3-dichlorobenzyl ammonium salt which have been found to provide superior results.
  • tributylbenzyl ammonium salt tributylnaphthyl ammonium salt, or a halo-substituted and, in particular, chlorine substituted benzyl or naphthyl derivative thereof.
  • polyvinyl chloride fibers suitable for use in connection with the instant invention may be homopolymers, copolymers or polyvinyl chloride fibers which have after chlorinated. That is to say, that any polyvinyl chloride is suitable for use in connection herewith.
  • the subject process may be applied either to the fiber individually and/or to mixed knitted or woven fabrics comprising polyvinyl chloride either alone or in combination with other fabrics. It is noted that when the subject process is applied to a mixed spun product comprising polyvinyl chloride fiber in combination with another fiber which other fiber is preferably wool that one can advantageously dye both fibers simultaneously in one bath with the same acid dye.
  • the modified polyester fibers employed in connection with the instant invention are those so-called readily dyeable polyester fibers. That is to say, that said modified polyester fibers are those whose dyeability by means of dispersed dyes have been improved by heat treatment at elevated temperatures and/or by the introduction of a secondary component.
  • readily dyeable polyester fibers as employed herein is defined to mean those in which the percentage exhaustion of the dye bath as determined in accordance with JIS L 1060-1960 is above 70%. Satisfactory dyeings cannot be obtained even by the method of the instant invention in those situations wherein the percentage exhaustion of the dye bath is below the above-noted level.
  • the specimen is washed in a -fold amount of distilled water (70 C.) for 30 minutes with stirring, followed by air drying and thorough opening of the fiber.
  • distilled water 70 C.
  • the cellulose acetate fibers which may be employed in connection with the instant invention include diacetate or triacetate fibers. Furthermore, the instant invention is also applicable to so-called fiber-acetylated staples. As noted above, the process of the instant invention is also suitable for use in connection with mixed knit and/or woven knit or woven fabrics of the subject fibers in combination with other fibers. It is noted that the process of the instant invention is espesially effective in the case of mixed fibers wherein a cellulose acetate fiber is mixed with a polyamide fiber in view of the fact that both the polyamide and the cellulose acetate are dyeable with acid dyes.
  • the anionic dyestuffs suitable for use in connection with the instant invention are all dyestulfs which have an anionic group.
  • Exemplary of such dyestuffs are the acid dyes, direct dyes, metal complex dyes, mordant dyes, water-soluble reactive dyes, metal complex dyes of the dispersed type, and the like.
  • the use of an acid dye brings about a maximum effect and it is preferred that such a dye have a small number of water soluble groups in its dye molecule. Normally, a. dye having one to two water soluble groups gives an excellent effect.
  • the instant invention may be employed by any of the conventional techniques such as dipping, padding or printing wherein the dyestulf is contacted with a textile in any form such as a staple yarn, fabric form, and the like.
  • the conditions for dyeing are varied depending upon the class of textiles employed therefor, and, further the dyeing technique utilized.
  • modified polyester fiber In the event modified polyester fiber is to be dyed, about 1l00% O.W.F. of the aforesaid compound is added to the dye bath and the dyeing is generally carried out at a temperature above approximately 100 C. and preferably, at a temperature of from about 110 to about 130 C. until the intended depth of color phase is obtained.
  • the dyeing is generally carried out at a temperature above approximately 100 C. and preferably, at a temperature of from about 110 to about 130 C. until the intended depth of color phase is obtained.
  • from about 1l00% O.W.F. of the above-noted compound is added to the dye bath and dyeing is carried out at a temperature of from about 80 to about 120 C. It is noted, that preferably the temperature is as high as possible so long as no adverse effects incurred thereby.
  • the process of the instant invention may be further enhanced by employing conventional carriers as dyeing acceleratingagents.
  • suitable carriers are phenolic compounds such as oand p-phenylphenol, the chlorobenzene compounds such as monochlorobenzene, o-dichlorobenzene, and trichlorobenzene, the benzoic acid compounds such as benzoic acid and salicylic acid, naphthalene compounds such as methyl naphthalene, and the like.
  • those which are water-soluble may be added to the dye bath as an aqueous solution whereas those which are water-insoluble are added in the form of a dispersion or an emulsion.
  • a non-ionic surfactant is also preferably employed in connection with the process of the instant invention in an amount suitable therefor.
  • the nonionic dyestuff is generally employed as a leveling agent so as to thoroughly disperse the dye and prevent said dye from turning tarry, thus, enhancing the ultimate dyeing.
  • Such surfactants are those which are commonly employed as dispersing agents and include for example, polyethylene glycol type surfactants such as polyethylene glycol alkylamine, polyethylene glycol alkyl ethers and polyethylene glycol aliphatic acid esters, and the ether or ester type surfactants having polyhydric alcohols as their hydrophilic group, such as sorbitan aliphatic acid esters and aliphatic acid monoglycerides.
  • the fibers which have been dyed according to the invention method are, after dyeing, subjected to thorough soaping and, if necessary, to reduction clearing, and the dyeing is fully colorfast after these post treatments.
  • the water-soluble or water-dispersible dye forms a complex with the aforesaid compound to become less insoluble in water and at thesame time becomes compatible with and have affinity for the hydrophobic fiber, with the consequence that this compound diffuses into the interior of the fiber owing to the elevated temperature and, at times, the action of the carrier to elfect the adsorption of the dye.
  • the balance between the size of the complex of the dye and the compound and its compatibility and afiinity relative of the hydrophobic fiber becomes an important factor in determining the amount of dye adsorption.
  • the intended results cannot be obtained only by making dyes water insoluble. The intended results can be only obtained when the specific compounds prescribed by this invention are used.
  • the dye product obtained was subjected to washing thoroughly with water and soaping with a solution containing 1 gram of soap at 60 C. for 20 minutes.
  • the dye product obtained exhibited a bright red shade and the adsorption ratio of dye was 85 EXAMPLE 2
  • Example 1 When Example 1 was repeated except that a compound of the formula was used instead of the cationic compound, used in said example, a product dyed a deep bright red shade was obtained.
  • EXAMPLE 3 A 1:1 type metal complex dyestufi Neolan Black WA (0.11. Acid Black 52, 0.1. No. 15711) having the formula: Chromium complex derived from 10 grams of a modified polyethylene terephthalate fiber (dye uptake about 85% as determined by the aforesaid J IS method) were dipped in a dye bath of the fore going composition prepared by adding 6 grams of the above-noted dyestutf and 10 grams of polyoxyethylene laurel ether which served as a dye-dispersing agent to 10 liters of water and grams of a-methyl naphthalene as a carrier.
  • EXAMPLE 4 A dye bath comprising the following was prepared: Suminol Fast Red B of Example 5 (CI. Actd Red 6)-4% O.W.F. n-Tributylbenzyl ammonium chloride-4% O.W.F. Nonionic surfactant of Example 11 g./liter Goods to liquor ratio1 :50
  • the dyeing was conducted at 130 C. for 90 minutes subsequent to which the temperature was gradually lowered and the dye product removed therefrom. Subsequent to removal the dye product was washed thoroughly with water and accordingly to the customary technique and subjected to soaping with a solution containing 1 g./liter of soap at 80 C. for minutes. After drying the dye product it was found to have a bright deep red shade.
  • Example 8 The procedure of Example 3 was repeated utilizing in lieu of the dyestuff therein a 1:2 type metal complex dyestufi Neolan Red B (C.I. Acid Red 201, CI. No. 18761) having the structure:
  • EXAMPLE 6 Instead of the dye used in Example 3, 0.6 g. (6%) of a mordant dye (C.I. No. 14645, C.I. Mordant Black 11) med a: 4?
  • a dye dispersing agent serving as a dye dispersing agent.
  • 1 g. (10%) of a cation compound of n-tributylbenzyl ammonium chloride and a carrier of emulsified a methyl naphthalene were further added in this solution whereby a dye liquor was made.
  • This dye liquor was charged in the dye bath of a high pressure dyeing apparatus and water was added to adjust a goods-to-liquor ratio 1:50. The total amount of the dye liquor was kept to 500 cc.
  • Example 8 The procedure of Example 7 was repeated with the exception that a triacetate fiber was used in lieu of a diacetate fiber. The dyeing was carried out at a temperature of 120 C. and the product dyed a deep blue shade was obtained.
  • EXAMPLE 10 A polyacrylonitrile staple fiber was dyed for 60 minutes at 110 C. with the use of a dye bath of the composition indicated below, and a deep red dyeing was obtained.
  • EXAMPLE 11 A polyacrylonitrile staple fiber was dyed for 60 minutes at 100 C. with the use of a dye bath of the composition indicated below, and a deep yellow dyeing was obtained.
  • EXAMPLE 12 A crepe de Chine diacetate fabric was dipped in a bath having the following composition:
  • Nonionic surfactant of the formula:
  • EXAMPLE 13 A crepe de Chine diacetate fabric was printed using a paste having the following composition:
  • Z is a group selected from benzyl, naphthyl; substituted beuzyl, wherein the substituent is selected from alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, and halogen, and substituted naphthyl, wherein the substituent is selected from alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, and halogen; and X is selected from the group consisting of halogen atom and lower alkyl sulfonic acid residue.

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US28121A 1966-01-22 1970-04-13 Method of dyeing textile fibers with an anionic dyestuff in the presence of a quaternary ammonium salt Expired - Lifetime US3700399A (en)

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3879170A (en) * 1971-12-23 1975-04-22 Rhone Poulenc Textile Method of acid dyeing polyester fibers
US3987097A (en) * 1971-03-15 1976-10-19 Sandoz Ltd. Quaternary ammonium halides
US4025300A (en) * 1974-01-17 1977-05-24 Rhone-Poulenc-Textile Process of dyeing articles made from polyesteramines
US4098821A (en) * 1976-10-18 1978-07-04 The Dow Chemical Company Quaternary ammonium phenates containing a (3-chloro-2-propenyl) group
US4369041A (en) * 1980-05-12 1983-01-18 Vyzkumny Ustav Zuslechtovaci Technique for dyeing and printing of textiles with quaternary ammonium compound
WO2002009543A1 (fr) * 2000-07-31 2002-02-07 Kaneka Corporation Procédé de teinture pour cheveux artificiels
RU2429321C1 (ru) * 2010-03-09 2011-09-20 Государственное образовательное учреждение высшего профессионального образования "Санкт-Петербургский государственный университет технологии и дизайна" Состав для крашения текстильных материалов из полиэфирных волокон

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7140070B2 (ja) * 2019-07-24 2022-09-21 日東紡績株式会社 混用染色布帛及びその製造方法

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3987097A (en) * 1971-03-15 1976-10-19 Sandoz Ltd. Quaternary ammonium halides
US3879170A (en) * 1971-12-23 1975-04-22 Rhone Poulenc Textile Method of acid dyeing polyester fibers
US4025300A (en) * 1974-01-17 1977-05-24 Rhone-Poulenc-Textile Process of dyeing articles made from polyesteramines
US4098821A (en) * 1976-10-18 1978-07-04 The Dow Chemical Company Quaternary ammonium phenates containing a (3-chloro-2-propenyl) group
US4369041A (en) * 1980-05-12 1983-01-18 Vyzkumny Ustav Zuslechtovaci Technique for dyeing and printing of textiles with quaternary ammonium compound
WO2002009543A1 (fr) * 2000-07-31 2002-02-07 Kaneka Corporation Procédé de teinture pour cheveux artificiels
US20030154564A1 (en) * 2000-07-31 2003-08-21 Hiroyuki Nakashima Method of dyeing artificial hair
US7018421B2 (en) * 2000-07-31 2006-03-28 Kaneka Corporation Process for dyeing synthetic hair
KR100758682B1 (ko) * 2000-07-31 2007-09-13 가부시키가이샤 가네카 인공 모발의 염색 방법
RU2429321C1 (ru) * 2010-03-09 2011-09-20 Государственное образовательное учреждение высшего профессионального образования "Санкт-Петербургский государственный университет технологии и дизайна" Состав для крашения текстильных материалов из полиэфирных волокон

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