US3788811A - Solvent compositions for solvent dyeing and dyestuff solutions prepared therefrom - Google Patents

Solvent compositions for solvent dyeing and dyestuff solutions prepared therefrom Download PDF

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US3788811A
US3788811A US00144603A US3788811DA US3788811A US 3788811 A US3788811 A US 3788811A US 00144603 A US00144603 A US 00144603A US 3788811D A US3788811D A US 3788811DA US 3788811 A US3788811 A US 3788811A
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solvent
organic
composition
dyeing
clear
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F Sievenpiper
E Bement
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Honeywell International Inc
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Allied Chemical Corp
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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
    • 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
    • D06P1/90—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 dyes dissolved in organic solvents or aqueous emulsions thereof
    • D06P1/92—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 dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents
    • D06P1/922—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 dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents hydrocarbons
    • D06P1/924—Halogenated hydrocarbons
    • 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
    • D06P1/90—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 dyes dissolved in organic solvents or aqueous emulsions thereof
    • D06P1/92—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 dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents
    • D06P1/928—Solvents other than hydrocarbons

Definitions

  • compositions in which many organic dyestuffs are soluble.
  • the novel compositions are stable, that is to say, they do not become cloudy or phase separate on standing.
  • Solvent compositions within the scope of the invention in which an organic dyestuff is dissolved provide excellent dyeings by a solvent dyeing procedure on a variety of textile fibers, both natural and man-made, which dyeings are free from spottiness and are of excellent fastness to washing, rubbing and the like.
  • FIGS. 1, 3, 4 and 5 of the drawing illustrate preferred embodiments of the invention and show those proportions of the indicated components which form clear, stable, homogeneous compositions which are also non-flammable under the conditions present in most dyeing procedures.
  • the figures are ternary diagrams in which the proportions Attempts to improve the proposed organic solvents for solvent dyeing procedures by using dyeing assistants, cosolvents, swelling agents and the like, have-givenunsatisfactory results such as by altering the properties of the fibers, by degrading the fastness of the dyes, or by causing precipitation of the dyestuff from solution and phase separation of the dyeing medium. This results in spottiness and tailing in the dyeings.
  • compositions are defined by the areas within the closed curves shown by the heavy black lines.
  • the composition of a point within such areas may be read along the axis indicated in volume percent.
  • FIG. 1 shows a preferred embodiment in which PERC. is perchloroethylene, EC. is ethylene carbonate and PM is 1-methoxy-2-hydroxypropane.
  • FIG. 3 shows a preferred embodiment in which PERC. is perchloroethylene, EC. is ethylene carbonate and EM. is methoxyethanol.
  • FIG. 4 shows a preferred embodiment in which PERC. is perchloroethylene, EC. is ethylene carbonate and EE. is ethoxyethanol.
  • FIG. 5 shows a preferred embodiment in which PERC. is perchloroethylene, H O is water and EE. is ethoxyethanol.
  • solutions is intended to cover dispersions in which the dyestuff is partially solubilized in the solvent.
  • dissolve is intended to refer to the state of solubilizing in which the final result will be a partially solubilized dye mixture, or a dye dispersion.
  • novel solvent compositions of the invention should be formulated so as to boil over a range of between about 50 C. and the softening point of the particular textile material being dyed, usually below about 180 C. for manmade textiles.
  • the novel compositions boil within the range of about to about 165 C. and, still preferably, between about -l60 C.
  • the volume ratio of the halogenated hydrocarbon component to the organic liquid component would be chosen to give the desired properties of dye solubility and non-flammability in the particular application involved. Then the polar liquid (swelling agent) is added. If the solution becomes cloudy, additional quantities of the other two components may be added until a clear solution results. Generally, it is desired to maximize the concentration of the halogenated hydrocarbon and minimize the concentration of the organic liquid, while giving a stable, clear solution with the desired quantity of polar liquid (swelling agent).
  • the halogenated hydrocarbon component of the novel compositions generally constitutes between about 25 and 94% by volume of the composition. Use of at least 25% by volume of the halogenated component will generally ensure that the resulting mixtures will be non-flammable under conditions normally encountered in most dyeing procedures. In a particular dyeing application, however, it may be necessary to increase the proportion of the halogenated component to ensure non-flammability. Preferably, this component is present in an amount between about 50 and 85% by volume and, still preferably, between about 70 and 85% by volume.
  • This component which serves principally as the vehicle for the dyestutf, may be aliphatic or aromatic, and generally boils between about 40 and about 180 C.
  • halogens may be selected from fluorine, chlorine, bromine and iodine, subject to the requirement that the compound is stable. This requirement will exclude a number of brominated and iodinated hydrocarbons.
  • suitable halogenated hydrocarbons include the following:
  • the polar liquid component must be a swelling agent for a textile fiber and must be substantially insoluble in the halogenated hydrocarbon component.
  • swelling agent it is intended to incude a substance which acts on a natural or synthetic textile fiber to accele ate diffusion therein of a dyestuff substantive thereto. As is well understood in the art, this does not necessarily mean that the swelling agent increases either a cross-sectional or longitudinal dimension of the fiber. In the case of natural fibers, it most frequently does however, in the case of synthetic fibers, no noticeable swelling of the fibers may take place.
  • the test for the purpose herein, as described above, is whether the agent in question accelerates diffusion of the dyestuff into the fiber.
  • substantially insoluble it is intended to mean less than about .1% by weight soluble.
  • the polar liquid is generally present in an amount within the range of about .1 to about 5% by volume of the total composition.
  • this component has a boiling point over 80 C. and preferably tions as a swelling agent on natural fibers such as cotton, is ineffective as a swellingagent on man-made fibers such as polyesters or polyamides Ethylene carbonate, on the other hand, which is effective as a swelling agent for many man-made fibers, such as acrylics, is not an effective swelling agent fornatural fibers.
  • the choice of the swel1- ing 'agent will accordingly depend upon the textile material which is to be dyed.
  • Suitable swelling agents may be aliphatic or aromatic in nature. We know of no carbon content limitations for the same. Typical examples of known swelling agents which are candidates for use in the appropriate system include the following:
  • the third component of the novel compositions is an organic liquid, boiling within the range of about 75 to about 180 C., and which is soluble in each of the halogenated hydrocarbon and the polar liquid to the extent of at least about 5% by weight.
  • This liquid is preferably selected from the group consisting of alcohols, ethers and ketones.
  • the organic liquid may be aliphatic or aromatic in nature and may include polyfunctional materials such as diketones, polyethers and polyhydroxy compounds. We know of no limitations on the carbon content for these liquids, subject, of course, to the boiling range requirements recited herein.
  • organic liquids are generally present in the composition in amounts within the range of about 5 to 75% by volume, preferably from about 7 to 40% by volume and, most preferably, from about 10 to 35% by volume.
  • the following are typical examples of this third component of the novel solvent mixtures:
  • alkoxyalkanols having from 2-4 carbon atoms in each of the ethoxy and ethanol moieties, such as:
  • the upper boiling point limit is not signifi methylethyl ketone diethyl ketone cyclopentanone cyclohexanone 2-methyl-cyclohexanone n-butyl, n-propyl ketone Mixtures of the above illustrated organic liquids may also be employed.
  • Surfactants of the anionic or non-ionic classes may be incorporated, if desired, into the solvent mixtures of this invention. When present, the overall dyeing performance of the mixtures may be improved.
  • the surfactant if present, is preferably used in amounts within the range of from 0.05 to 3% by weight of the solvent mixture and, still preferably, within the range of about 1 to 2% by weight. Larger concentrations may be employed, if desired.
  • Typical surfactants suitable for use in this instance include the following: i
  • the solvent mixtures of the invention provide excellent dyeingvehicles for-the solvent soluble forms of organic dyestuffs.
  • the resulting dyestulf containing compositions are suitable for dyeing synthetic and natural fibers.
  • the solvent mixtures are non-flammable, have high flash points and are readily volatilized for recovery and reuse. Because of the clear, stable, homogeneous character of the solvent mixtures of this invention, the dye solutions are evenly distributed on textile materials and thus provide spot-free dyeings thereon.
  • Theorganic, dyestulf is used in a solvent soluble form.
  • solvent soluble form is meant a form in which the dyestuif .is substantially free of the usual inorganic salts present as strength reducing agents, dispersants, and the like.
  • Many dyestuffs of the acid, direct, and basic classes are usually marketed as mixtures with inorganic salts such as sodium sulfate and sodium chloride, which are added to reduce the coal tar dyestuff content.
  • inorganic salts are generally insoluble in the organic solvent mixtures of the invention.
  • such salts can be readily removed from these dyestulf compositions by well known means,'for example, by extraction with an organic solvent.
  • the solventsoluble forms of organic dyestuffs accordingly may contain substantial quantities of coal tar dyestuffs. x I
  • a preferred form .oflorga'nic dyestuffs for use in this invention is as organic salts of the dyestuffs.
  • organic salts for example, may be formed by reaction of an. acid or direct dye containing at least one sulfonic acid group or alkali metal salt thereof, with an organic base, such as an amine, forvexample, dioctyl amine, dicyclohexylamine, ditolyl guanidine, and thelike.
  • organic base such as an amine, forvexample, dioctyl amine, dicyclohexylamine, ditolyl guanidine, and thelike.
  • the preparation of such organic salts of organic dyestuffs is described in the patent literature, for example, in US. Pat. 1,647,-
  • dyes of the basic dye class are soluble in organic solvents per se or can be rendered soluble by reaction of the cationic portion of the. basic dye molecule with an organic acid such as benzoic acid, propionic acid, and
  • Exemplary of the dyes suitable for use in conjunction with the solvent mixtures of the present invention are 'the solvent soluble forms of the following .known dyestuffs. (The Color Index numbers, where. available, are
  • the dyestuffs are generally employed from about 0.01 to about 3 parts by weight, and preferably from about 0.02 to about 3 parts by weight of solvent soluble dye per parts of the total solvent mixture. It will be obvious to those skilled in the art that the selection of the dyestuff will depend upon the textile material being dyed and that the composition of the solvent mixture will depend upon the nature of the dyestulf as well as upon the textile material being dyed. Thus, woolen or cellulosic textile materials would call for solvent soluble forms of acid or direct dyestuffs dissolved in solvent mixtures containing water as the swelling agent. Acrylic textile materials would call for solvent soluble forms of :basic dyes dissolved in solvent mixtures containing an organic swelling agent for this fiber, such as ethylene carbonate.
  • the organic'dyestulf solvent compositions of the present invention may be used to dye textiles by the same procedures and techniques employed in the aqueous dyeing of textiles.
  • the dyestulf solution is applied to the textile material, for example, cotton or rayon, by any suitable'means, such as by padding, spraying, dipping, flooding, or the like, and the dyestulf impregnated material may then be passed into a zone of perchloroethylene vapors maintained at about to C. for about one minute in order to fix the dyestulf on the fiber.
  • the dyeing is done by dipping in a dyestulf solvent bath
  • fixing may be accomplished in situ :by heating the bath.
  • the dyed textile may then be rinsed in a solvent bath and dried.
  • the finished dyed product is colorfast to aqueous soap solutions and dry cleaning solvents.
  • EXAMPLE 1 was added. The mixture was gently agitated and rapidly became clear and homogeneous. 7
  • EXAMPLE 2 A mixture of 100 parts of ethoxyethanol, parts of ethylene carbonate, 200 parts of methylene chloride and 500 parts of 1,1,1-trichloroethane was prepared by mixing the above components in the indicated proportions. The resulting clear solution was used to dissolve 2 parts by weight of the free base form of CI Basic Orange 22 (CI 48040). The resulting clear dyestuft solution was sprayed on a pile fabric composed of 70% by weight of a copolymer of polyvinyl chloride and of acrylonitrile, by weight of a polyacrylonitrile polymer and 10% by weight of nylon. The dye solution impregnated fabric was passed into a chamber and exposed for several minutes to superheated vapors of perchloroethylene at about 143 C. The fabric was then removed from the chamber and allowed to dry in the air at ambient temperature. The fabric was dyed a bright level orange shade. The fixation of the dye thereon was excellent.
  • EXAMPLE 3 The following experiment illustrates the elfect of varying the proportions of the various components of the ternary solvent mixtures of the invention on the clarity or homogeneity of the mixtures.
  • 11 parts of water were mixed with increasing volumes of perchloroethylene and thereafter the volumes of ethoxyethanol required to obtain clear solutions were determined.
  • the water component contained dioctyl sodium sulfosuccinate, an anionic surfactant, in the amount of 1 part by weight of surfactant per 10 parts of water.
  • Table I See Fig. 5. Comparable results are obtained with the same components in the absence of surfactant.
  • E C ethylene carbonate.
  • PE R C perch10ro ethylene.
  • EE. ethoxyethano1.
  • EXAMPLE 4 A solution of CI Basic Red 18 250% was prepared by adding 10 parts by weight of the dyestuif to 86 parts of a 2 to 1 by volume mixture of ethoxyethanol and ethylene carbonate, gently agitating the mixture while heating it to 65 C. and, after permitting the mass to cool to ambient temperature, filtering it to remove about 0.34 part by weight of insoluble material. 1
  • a stable,.clear solvent solution was prepared by dissolving 25 parts by weight of alkylphenoxypoly (ethyleneoxy)ethanol in 225 parts of ethoxyethanol, and then adding 50 parts of water and parts of perchloroethylene in succession to the mixture.
  • EXAMPLE 5 A mixture of 10 parts by weight of Cl. Basic Blue 45 480%, 60 parts by'weight of ethoxyethanol and 30 parts by weight of ethylene carbonate, was warmed to 50C. The mixture was agitated at 50 C; for five minutes and thenpermitted to cool to ambient temperature after which the mass was filtered to remove about 2 parts of insoluble material.
  • a solvent mixture was prepared by dissolving 15 parts by weight of the isopropylamine salt of dodecylbenzene sulfonic acid (M.W. 350) in 310 parts of ethoxyethanol, then adding in succession to the solution 30 parts of water and 750 parts of perchloroethylene. A clear solution resulted.
  • a dye solution was prepared by mixing 2.08 parts by weight of the Cl. Basic Blue 45 solution, prepared above, with 97.92 parts by weight of the solvent mixture, prepared above.
  • the resulting solution was padded on 13 parts by weight of an acrylic textile.
  • the padded material was passed through squeeze rollers to adjust the pick-up of dye solution to 16 parts by weight.
  • the impregnated cloth was passed into a zone of solvent vapors, heated to about 145 C. and held therein for about 3 minutes.
  • the cloth was next passed into about 190 parts of perchloroethylene and the solvent-scoured cloth was dried. The dried cloth was then washed in a bath containing 1000 parts of water and 2 parts by weight of an alkylaryl sulfonate detergent.
  • the acrylic textile was dyed a deep blue, which dyeing had excellent wash fastness as evidenced by the clarity and color free nature of the washing liquor. 'Ihe dyeing also possessed excellent fastness to crocking which indicates that the fixation of the dye on the fabric was excellent.
  • a clear, stable, homogenous solvent solution composition which consists essentially of a three component mixture of (A) about 25-94% by volume of a stable halogenated hydrocarbon boiling within the range of about 40 to about C., i p v e (B) about 0.1 to 5% by volume 'of a polar liquid which f is a swelling agent for a textile fiber and which. is
  • a solvent composition as defined in claim 1 containing from about 70 85% by volume of" the halogenated hydrocarbon, from about 3 to 5% by volume of the polar (C) about to 75% by volume of l-methoxy-Z-hy- I droxypropane.
  • a solvent composition as defined in claim 1 in which the halogenated hydrocarbon is 1,1,1-trichloroethane.
  • a clear, stable, homogenous solvent solution composition which comprises a mixture of:
  • a solvent composition as defined in claim 1 containing as an additional component a nonionic or an anionic surfactant.
  • a solvent composition as defined in claim 5 in which the halogenated hydrocarbon is perchloroethylene, the polar liquid is ethylene carbonate, the organic liquid is 1-methoxy-Z-hydroxypropane, and in which the volume proportions of the recited components in the mixture are defined by the area within the closed curve shown in FIG. 1.
  • a solvent composition as defined in claim 12 containing as an additional component a nonionic or an anionic surfactant.
  • a solvent composition as defined in claim 14 containing as an additional component a nonionic or anionic surfactant.
  • a solvent composition as defined in claim 16 containing as an additional component a nonionic or an anionic surfactant.
  • a solvent composition as defined in claim 13 in which the halogenated hydrocarbon is perchloroethylene, the polar liquid is water, the organic liquid is ethoxyetha- 1101, and in which the volume proportions of the recited components in the mixture are defined by the area within the closed curve shown in FIG. 5.
  • a solvent composition as defined in claim 18 containing as an additional component a nonionic or an emonic surfactant.
  • a dyestuff composition comprising an organic dyestufit' dissolved or dispersed in a clear, stable, homogeneous solvent composition as defined in claim 1.
  • a dyestufi' composition comprising an organic dyestufi dissolved or dispersed in a clear, stable, homogeneous solvent composition as defined in claim 4.
  • a dyestulf composition comprising an organic dyestuif dissolved or dispersed in a clear, stable, homogeneous solvent composition as defined in claim 5.
  • a dyestuff composition comprising an organic dyestuff dissolved or dispersed in a clear, stable, homogeneous solvent composition as defined in claim 6.
  • a dyestuif composition comprising an organic dyestuif dissolved or dispersed in a clear, stable, homogeneous solvent composition as defined in claim 7.
  • a dyestulf composition comprising an organic dyestufi' dissolved or dispersed in a clear, stable, homogeneous solvent composition as defined in claim 8.
  • a dyestulf composition comprising an organic dyestuff dissolved or dispersed in a clear, stable, homogeneous solvent composition as defined in claim 9.
  • a dyestufi composition comprising an organic dyestufi dissolved or dispersed in a clear, stable, homogeneous solvent composition as defined in claim 10.
  • a dyestufi composition comprising an organic dyestu'if dissolved or dispersed in a clear, stable, homogeneous solvent composition as defined in claim 11.
  • a dyestuff composition comprising an organic dyestuff dissolved or dispersed in a clear, stable, homogeneous solvent composition as defined in claim 12.
  • a dyestulf composition comprising an organic dyestufi dissolved or dispersed in a clear, stable, homogeneous solvent composition as defined in claim 13.
  • a dyestuff composition comprising an organic dyestuff dissolved or dispersed in a clear, stable, homogeneous solvent composition as defined in claim 14.
  • a dyestulf composition comprising an organic dyestuff dissolved or dispersed in a clear, stable, homogeneous solvent composition as defined in claim 15.
  • a dyestuff composition comprising an organic dyestutf dissolved or dispersed in a clear, stable, homogeneous solvent composition as defined in claim 16.
  • a dyestufi composition comprising an organic dyestufi dissolved or dispersed in a clear, stable, homogeneous solvent composition as defined in claim 17.
  • a dyestuflf composition comprising an organic dyestufi dissolved or dispersed in a clear, stable, homogeneous solvent composition as defined in claim 18.
  • a dyestuif composition comprising an organic dyestuff dissolved or dispersed in a clear, stable, homogeneous solvent composition as defined in claim 19.

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  • Textile Engineering (AREA)
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US00144603A 1971-05-18 1971-05-18 Solvent compositions for solvent dyeing and dyestuff solutions prepared therefrom Expired - Lifetime US3788811A (en)

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BE (1) BE783583A (enrdf_load_stackoverflow)
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FR (1) FR2137755B1 (enrdf_load_stackoverflow)
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3958934A (en) * 1973-06-05 1976-05-25 E. I. Du Pont De Nemours And Company Rapid fixation of disperse dyes on synthetic polymers
US5201959A (en) * 1990-08-01 1993-04-13 Fuller Benjamin F Apparatus for dyeing carpet
US10557231B2 (en) * 2014-03-21 2020-02-11 Commissariat à l'Energie Atomique et aux Energies Alternatives Method for coloring cellulose

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1586590A (enrdf_load_stackoverflow) * 1968-12-24 1970-02-20

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3958934A (en) * 1973-06-05 1976-05-25 E. I. Du Pont De Nemours And Company Rapid fixation of disperse dyes on synthetic polymers
US5201959A (en) * 1990-08-01 1993-04-13 Fuller Benjamin F Apparatus for dyeing carpet
US10557231B2 (en) * 2014-03-21 2020-02-11 Commissariat à l'Energie Atomique et aux Energies Alternatives Method for coloring cellulose

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FR2137755A1 (enrdf_load_stackoverflow) 1972-12-29
IT958880B (it) 1973-10-30
DE2222095A1 (de) 1972-11-30
FR2137755B1 (enrdf_load_stackoverflow) 1974-12-20
BE783583A (fr) 1972-09-18

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