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US20090158534A1 - Dyeing of Wool Fibres - Google Patents

Dyeing of Wool Fibres Download PDF

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Publication number
US20090158534A1
US20090158534A1 US12/083,181 US8318106A US2009158534A1 US 20090158534 A1 US20090158534 A1 US 20090158534A1 US 8318106 A US8318106 A US 8318106A US 2009158534 A1 US2009158534 A1 US 2009158534A1
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US
United States
Prior art keywords
dyeing
range
process according
wool
dye
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US12/083,181
Inventor
Manfred Jungen
Jean-Pierre Vierling
Udo Schmitt
Rino Marazzi
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Clariant Finance BVI Ltd
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Clariant Finance BVI Ltd
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Assigned to CLARIANT FINANCE (BVI) LIMITED reassignment CLARIANT FINANCE (BVI) LIMITED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: JUNGEN, MANFRED, MARAZZI, RINO, SCHMITT, UDO, VIERLING, JEAN-PIERRE
Publication of US20090158534A1 publication Critical patent/US20090158534A1/en
Abandoned legal-status Critical Current

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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
    • D06P1/60—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 polyethers
    • D06P1/607—Nitrogen-containing polyethers or their quaternary derivatives
    • D06P1/6076—Nitrogen-containing polyethers or their quaternary derivatives addition products of amines and alkylene oxides or oxiranes
    • 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
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/14—Wool

Definitions

  • This invention relates to a process for dyeing wool or wool-containing materials with the aid of a levelling agent to obtain uniform dyeings.
  • Levelling agents or assistants are generally surface-active textile dyeing auxiliaries which have the task of thoroughly wetting the fibre/fibre blend to be dyed, of promoting penetration of the fibres and of preventing too rapid uptake of the dyes, which can lead to unlevelness (spottiness), during the dyeing operation.
  • Suitable levelling assistants include oleylsulphonates, fatty alcohol sulphonates, various fatty acid condensation products, alkyl and alkylaryl polyglycol ethers and surface-active chemicals in general.
  • Levelling assistants reduce mainly the rate of dyeing, increase the rate of dye migration within the fibre and improve the compatibility of the dyes.
  • Levelling agents can also have other effects which have no direct influence on the dye-fibre interactions, but nevertheless exert a positive effect on the dyeing. These include the improved solubility or the dispersion stability of the dye.
  • Levelling assistants can exert two or more of the abovementioned effects at the same time.
  • Levelling assistants can be divided into two groups, those which have an affinity for the fibre and those which have an affinity for the dye.
  • Levelling assistants with an affinity for dyes form an addition compound with the dye whose stability is concentration dependent and normally decreases with increasing temperature.
  • the dye distribution equilibrium between the dye in solution and the dye in the fibre is therefore shifted to the dye in solution.
  • the increased dye concentration in the dye solution makes it possible for regions of the fabric which were dyed in a non-level manner to level out as a result of dye migration.
  • Effective levelling assistants have an affinity for the dye that is sufficient to reduce the absorption rate or to speed the migration rate. Differences in the absorption behaviour of different dyes can likewise be levelled, so that the dyes in a dye mixture can go on at a uniform rate.
  • Assistants with an affinity for dyes can also be used to level previously dyed materials. Assistants with an affinity for fibres go onto the fibre in competition with the dye. This competition reaction reduces the absorption rate and promotes the migration rate.
  • Important dye-affinity levelling assistant types for wool are nonionic surfactants or weakly cationic, ethoxylated compounds.
  • Important fibre-affinity levelling assistant types for wool are anionic compounds.
  • Levelling assistants used for wool are frequently ethoxylated amine compounds, partially quaternized, as disclosed for example in DE-A-28 41 800.
  • the present invention accordingly provides a process for dyeing fibre materials composed of wool, characterized in that one or more compounds of formula (I)
  • the active substance is a compound of formula (II)
  • the active substance is used as an aqueous solution wherein the concentration of active substance is in the range from 15% to 35% by weight.
  • concentration of active substance in the aqueous solution is in the range from 25% to 35% by weight and when 0.1% to 5% by weight of foam-suppressing substances are included as further additives.
  • the dyeing is usually carried out at a pH in the range from 2 to 9, preferably in the range from 3 to 8, and especially in the range from 4 to 7.
  • the liquor ratio is in the range from 2:1 to 80:1 in the case of a batch dyeing, preferably in the range from 5:1 to 30:1, and in the range from 5:1 to 500:1 in the case of a continuous dyeing, preferably in the range from 20:1 to 300:1.
  • X ⁇ represents a customary inorganic or organic anion such as halides (chloride, bromide, iodide), sulphate, methosulphate, phosphate or acetate. Chloride is preferred.
  • the present active substance is known (CAS No. 747377-35-1 and 133189-76-1) and is simple to prepare by alkoxylation of the corresponding fatty amine.
  • the alkoxylation can also be carried out with propylene oxide instead of ethylene oxide or ethylene oxide and propylene oxide, randomly or as a block, but ethoxylated amines give better results.
  • the alkoxylate obtained could be completely or partially sulphonated or sulphated, although here too the non-sulphonated and non-sulphated species demonstrate better efficacy.
  • the active substance contains in general 15 to 30 ethylene oxide (EO) units, preferably 17 to 19 EO.
  • the active substance is particularly preferably an oleylamine with 17 to 19 EO, which was quaternized with 1 EO and contains chloride as counter-ion.
  • foam-suppressing substances can be used such as biocides, if desired or necessary dispersing assistants or wetting agents, for example sulphonated or sulphated alkyl, alkenyl or aryl polyglycol ethers, sulphonated or sulphated alkyl, alkenyl or aryl amine polyglycol ethers, and if desired or necessary defoamers based on silicone oil or mineral oil. It is preferable to use 2-ethylhexylisononanamide as foam-suppressing substance and a C 12-15 -alcohol with 8 ethylene oxide and 4 propylene oxide units as wetting component with an additional foam-suppressing effect.
  • biocides if desired or necessary dispersing assistants or wetting agents
  • dispersing assistants or wetting agents for example sulphonated or sulphated alkyl, alkenyl or aryl polyglycol ethers, sulphonated or sulphated al
  • the present levelling agent is not only advantageous in relation to the reactive dyes used in the examples which follow, but also displays good efficacy in relation to the dyeing of wool with acid dyes.
  • Material 1 tall graduated cylinder, peristaltic pump, rubber hose, 2 glass tubes, 1 long one reaching from 1 cm above the floor to the end of the cylinder and which is connected by a rubber hose, which leads through the pump, to a short, second glass tube situated at the level of a typical Ross Miles apparatus.
  • Concentration 2 g/l surfactant test solution in neutral or alkaline medium
  • a glass tube transports the solution from the floor (1 cm above) of the cylinder through a rubber hose by means of a peristaltic pump to the second glass tube, where the solution falls into the cylinder.
  • the solution is continuously recirculated at 180 ml/min.
  • the foam height after 1 minute, 5 minutes and 10 minutes is noted.
  • the pump is stopped after 10 minutes.
  • the foam height 1 minute after the pump has been switched off is noted as well.
  • the liquor is introduced into the dyeing apparatus followed, after the flow has stabilized, by the textile material. After heating with full power at room temperature to 98° C., the fabric is treated at 98° C. for 15 min, and then cooled back down to 70° C. and subsequently rinsed with cold water for 10 min.
  • the fabric columns are illustrated as follows:
  • Sample taken The fabric column is divided into 4 equal parts. Sample taking from the column: bottom, after 1 ⁇ 4, 1 ⁇ 2, 3 ⁇ 4 and top. Evaluation: The penetration of the substrate column is evaluated.
  • the assessment is done visually against the product to be compared.
  • the loaded material-carrier is introduced into the dyeing apparatus, followed by the dyeing liquor. 5 min at room temperature are followed by heating at 1° C./min to 98° C., dyeing at 98° C. for 60 min, then cooling down to 70° C. and subsequently rinsing with cold water.
  • ammonia solution 1 ml/l conc. about 25% pH 8.5-9.0 (care must be taken to ensure that the pH stays in this range during the treatment time)
  • the loose wool fibre, now dyed, is evaluated visually.
  • the purpose of the skitteriness assessment is to even out the hue and/or depth of shade difference between the wool root and the wool tip.
  • the dyeing beakers filled with dyeing liquor are introduced into the dyeing apparatus, followed by the wool gaberdine on the material-carriers. 5 min at room temperature are followed by heating at 1° C./min to 98° C., dyeing at 98° C. for 60 min, then cooling down to 70° C. and subsequently rinsing with cold water.
  • ammonia solution 1 ml/l conc. about 25% pH 8.5-9.0 (care must be taken to ensure that the pH stays in this range during the treatment time)
  • the wool gabardine, now dyed, is evaluated calorimetrically (relative colour strength and residual colour difference).
  • the utilized active substance (AS) had the following formula:
  • Formulation 34.5% of AS, 1.08% of C 12-15 -alcohol with 8 ethylene oxide and 4 propylene oxide units, 0.12% of ethylhexylisononanamide, remainder water.
  • Formulation 34.5% of AS, 1.08% of C 12-15 -alcohol with 8 ethylene oxide and 4 propylene oxide units, 0.12% of ethylhexylisononanamide, 2.0% of cumene sulphonate (40% in water), remainder water.
  • the utilized active substance had the following formula where X ⁇ is chloride:
  • the active substance utilized was a compound as described in DE-A-2 841 800

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

Abstract

The present invention relates to a process for dyeing fibre materials composed of wool wherein an alkoxylated and quaternized fatty acid amine, preferably a quaternized, ethoxylated oleylamine, is used as a levelling agent. The present compound leads to very uniform dyeings and is very effective in low concentrations.

Description

  • This invention relates to a process for dyeing wool or wool-containing materials with the aid of a levelling agent to obtain uniform dyeings.
  • Levelling agents or assistants are generally surface-active textile dyeing auxiliaries which have the task of thoroughly wetting the fibre/fibre blend to be dyed, of promoting penetration of the fibres and of preventing too rapid uptake of the dyes, which can lead to unlevelness (spottiness), during the dyeing operation. Suitable levelling assistants include oleylsulphonates, fatty alcohol sulphonates, various fatty acid condensation products, alkyl and alkylaryl polyglycol ethers and surface-active chemicals in general.
  • Unlevelness is caused by:
      • High and varying substantivity of the dye on the fibre
      • High and varying affinity of the fibre for the dye
      • Uneven distribution of the dye solution on the fibre
      • Temperature differences on the fibre
  • Insufficient levelness can be prevented by means of suitable dyeing techniques (including improving the diffusion of the solution within the fabric, pH control) and by means of levelling assistants.
  • Levelling assistants reduce mainly the rate of dyeing, increase the rate of dye migration within the fibre and improve the compatibility of the dyes.
  • Levelling agents can also have other effects which have no direct influence on the dye-fibre interactions, but nevertheless exert a positive effect on the dyeing. These include the improved solubility or the dispersion stability of the dye.
  • Levelling assistants can exert two or more of the abovementioned effects at the same time.
  • Levelling assistants can be divided into two groups, those which have an affinity for the fibre and those which have an affinity for the dye.
  • Levelling assistants with an affinity for dyes form an addition compound with the dye whose stability is concentration dependent and normally decreases with increasing temperature.
  • The dye distribution equilibrium between the dye in solution and the dye in the fibre is therefore shifted to the dye in solution. The increased dye concentration in the dye solution makes it possible for regions of the fabric which were dyed in a non-level manner to level out as a result of dye migration.
  • Effective levelling assistants have an affinity for the dye that is sufficient to reduce the absorption rate or to speed the migration rate. Differences in the absorption behaviour of different dyes can likewise be levelled, so that the dyes in a dye mixture can go on at a uniform rate.
  • Assistants with an affinity for dyes can also be used to level previously dyed materials. Assistants with an affinity for fibres go onto the fibre in competition with the dye. This competition reaction reduces the absorption rate and promotes the migration rate.
  • Important dye-affinity levelling assistant types for wool are nonionic surfactants or weakly cationic, ethoxylated compounds.
  • Important fibre-affinity levelling assistant types for wool are anionic compounds.
  • Levelling assistants used for wool are frequently ethoxylated amine compounds, partially quaternized, as disclosed for example in DE-A-28 41 800.
  • Yet there still continues to be a need for even more effective levelling agents.
  • It has now been found that, surprisingly, quite specific quaternized and ethoxylated amine compounds based on unsaturated fatty acids are very useful as levelling agents for wool.
  • The present invention accordingly provides a process for dyeing fibre materials composed of wool, characterized in that one or more compounds of formula (I)
  • Figure US20090158534A1-20090625-C00001
      • where
      • R is singly or doubly unsaturated alkenyl of 12 to 24 carbon atoms,
      • X− is an anion, and
      • (n+m) has an average value in the range from 14 to 29,
      • are used as active substance of a levelling agent.
  • The above process is advantageous when
      • R is a radical derived from oleic acid, linoleic acid or linolenic acid,
      • X− is chloride, bromide, iodide, methosulphate, sulphate, phosphate or acetate, and
      • (n+m) has an average value in the range from 17 to 19.
  • Preferably, the active substance is a compound of formula (II)
  • Figure US20090158534A1-20090625-C00002
      • where
      • (n+m) has an average value in the range from 17 to 19.
  • Advantageously, the active substance is used as an aqueous solution wherein the concentration of active substance is in the range from 15% to 35% by weight.
  • It is particularly advantageous when the concentration of active substance in the aqueous solution is in the range from 25% to 35% by weight and when 0.1% to 5% by weight of foam-suppressing substances are included as further additives.
  • Depending on the dye, the dyeing is usually carried out at a pH in the range from 2 to 9, preferably in the range from 3 to 8, and especially in the range from 4 to 7.
  • It is further advantageous when the liquor ratio is in the range from 2:1 to 80:1 in the case of a batch dyeing, preferably in the range from 5:1 to 30:1, and in the range from 5:1 to 500:1 in the case of a continuous dyeing, preferably in the range from 20:1 to 300:1.
  • X− represents a customary inorganic or organic anion such as halides (chloride, bromide, iodide), sulphate, methosulphate, phosphate or acetate. Chloride is preferred.
  • The present active substance is known (CAS No. 747377-35-1 and 133189-76-1) and is simple to prepare by alkoxylation of the corresponding fatty amine. The alkoxylation can also be carried out with propylene oxide instead of ethylene oxide or ethylene oxide and propylene oxide, randomly or as a block, but ethoxylated amines give better results. Furthermore, the alkoxylate obtained could be completely or partially sulphonated or sulphated, although here too the non-sulphonated and non-sulphated species demonstrate better efficacy. The active substance contains in general 15 to 30 ethylene oxide (EO) units, preferably 17 to 19 EO. The active substance is particularly preferably an oleylamine with 17 to 19 EO, which was quaternized with 1 EO and contains chloride as counter-ion.
  • As well as the foam-suppressing substances mentioned, further additives can be used such as biocides, if desired or necessary dispersing assistants or wetting agents, for example sulphonated or sulphated alkyl, alkenyl or aryl polyglycol ethers, sulphonated or sulphated alkyl, alkenyl or aryl amine polyglycol ethers, and if desired or necessary defoamers based on silicone oil or mineral oil. It is preferable to use 2-ethylhexylisononanamide as foam-suppressing substance and a C12-15-alcohol with 8 ethylene oxide and 4 propylene oxide units as wetting component with an additional foam-suppressing effect.
  • The present levelling agent is not only advantageous in relation to the reactive dyes used in the examples which follow, but also displays good efficacy in relation to the dyeing of wool with acid dyes.
    • EXAMPLES
  • The examples which follow illustrate the invention. Unless otherwise stated, parts and % are by weight.
    • Test Methods
  • Some test methods well known to one skilled in this art will now be described.
    • Ross-Miles Foam Test
      • The volume of foam is measured after a certain amount of liquid has been poured from a certain height, instantly and also after a one minute wait.
      • A 1000 ml graduated cylinder 60 mm in internal diameter and 430 mm in internal height is used. The test liquid is allowed to pour out from a 2 l separating funnel through a capillary 70 mm in length and 2 mm in internal diameter from a height of 600 mm, measured from the outlet of the capillary above the floor of the cylinder.
      • 500 ml of the solution to be tested are filled into the separating funnel and allowed to flow out into the graduated cylinder at the capillary-controlled efflux rate of about 0.17 l/min. As soon as the entire solution has flowed out, a stop watch is started and the entire volume (foam volume plus solution volume) is read off the cylinder scale. The reading is repeated after one minute.
      • The alkaline foam performance is tested using a surfactant concentration of 2 g/l in 2° Bé—NaOH solution in demineralized water, with 2° Bé—NaOH being equivalent to 12 g/l NaOH solid or 30 ml/l of 36° Bé NaOH. The test temperature is in the range from 20 to 25° C.
    Foam Test by Continuous Flow Method
  • Material: 1 tall graduated cylinder, peristaltic pump, rubber hose, 2 glass tubes,
    1 long one reaching from 1 cm above the floor to the end of the
    cylinder and which is connected by a rubber hose, which leads
    through the pump, to a short, second glass tube situated at the level of
    a typical Ross Miles apparatus.
    Concentration: 2 g/l surfactant test solution in neutral or alkaline medium
    Procedure: 1.00 g of surfactant is dissolved at room temperature (always exactly
    the same) in exactly 500 ml of deionized water and stirred until a
    homogeneous solution or mixture is obtained. This mixture is
    carefully introduced into the 1 l graduated cylinder (previously
    washed out with deionized water), so that no foam is formed. A glass
    tube transports the solution from the floor (1 cm above) of the cylinder
    through a rubber hose by means of a peristaltic pump to the second
    glass tube, where the solution falls into the cylinder. The solution is
    continuously recirculated at 180 ml/min. The foam height after
    1 minute, 5 minutes and 10 minutes is noted. The pump is stopped
    after 10 minutes. The foam height 1 minute after the pump has been
    switched off is noted as well.
    • Levelling Effect in Reactive Dyeing of Wool Material
  • Wool gaberdine, prewashed.
    • Apparatus
  • Colorstar from Mathis with special insert for columns
    • Dyeing Conditions
  • Liquor ratio 15:1; demineralized water
  • Through flow: 35 ml/min (5 l/min.kg=⅓ circulation/min)
    • Dye
  • Dyeing was carried out using various concentrations (⅓ and 1/1 standard depth of shade) of mono- and polyfunctional reactive dyes, for example Reactive Yellow 125, Reactive Yellow 176, Reactive Red 49 or mixtures thereof (Drimaren® dyes from Clariant) and also with Drimaren® Blue W-RL.
    • Dyeing Liquor
  • Levelling agent x x %
    Glauber salt calc. 5 5 %
    Sodium acetate cryst. 1 1 g/l
    Acetic acid pH 5 5
    x = without and with increasing amounts of levelling agent (for example 1 and 3%)
    • Dyeing Procedure
  • The liquor is introduced into the dyeing apparatus followed, after the flow has stabilized, by the textile material. After heating with full power at room temperature to 98° C., the fabric is treated at 98° C. for 15 min, and then cooled back down to 70° C. and subsequently rinsed with cold water for 10 min.
    • Assessment
  • The fabric columns are illustrated as follows:
  •
    Sample taken: The fabric column is divided into 4 equal parts.
    Sample taking from the column: bottom, after
    ¼, ½, ¾ and top.
    Evaluation: The penetration of the substrate column is evaluated.
  • The assessment is done visually against the product to be compared.
    • Skitteriness Test in Reactive Dyeing of Wool Material
  • Loose wool fibre washed, ready for dyeing, untreated wool
    • Apparatus
  • Turby from Mathis with device for dyeing loose substrates
    • Dyeing Conditions
  • Liquor ratio 20:1; demineralized water
  • Circulation level 10
    • Dye
  • Dyeing was carried out with the same dyes and concentrations as in the preceding test series.
    • Dyeing Liquor
  • Levelling agent x x %
    Glauber salt calc. 5 5 %
    Sodium acetate cryst. 1 1 g/l
    Acetic acid pH 5 5
    x = without and with increasing amounts of levelling agent (for example 1 and 3%)
    • Dyeing Procedure
  • The loaded material-carrier is introduced into the dyeing apparatus, followed by the dyeing liquor. 5 min at room temperature are followed by heating at 1° C./min to 98° C., dyeing at 98° C. for 60 min, then cooling down to 70° C. and subsequently rinsing with cold water.
    • Aftertreatment
  • The previously rinsed dyeings are aftertreated as follows on the same dyeing apparatus without intervening drying:
  •
    ammonia solution 1 ml/l
    conc. about 25%
    pH 8.5-9.0 (care must be taken to ensure that the pH
    stays in this range during the treatment time)
  • Start at room temperature, heat at full power to 85° C., treat for 20 min, then rinse cold.
    • Evaluation
  • The loose wool fibre, now dyed, is evaluated visually. The purpose of the skitteriness assessment is to even out the hue and/or depth of shade difference between the wool root and the wool tip.
  • Rating Against Dyeing without Levelling Agent:
  • No improvement, slight improvement (still distinct difference between root/tip but significantly less than without levelling agent, distinct improvement (very small differences between root/tip), good (no differences between root/tip)
    • Colour Build-Up Enhancement in Reactive Dyeing of Wool Material
  • Wool gaberdine, prewashed
    • Apparatus
  • Vistacolor from Mathis with device for piece dyeing
    • Dyeing Conditions
  • Liquor ratio 20:1; demineralized water
  • Stroke level 10, with twist
    • Dye
  • Dyeing was carried out with the same dyes and concentrations as in the preceding test series.
    • Dyeing Liquor
  • Levelling agent x x %
    Glauber salt calc. 5 5 %
    Sodium acetate cryst. 1 1 g/l
    Acetic acid pH 5 5
    x = without and with increasing amounts of levelling agent (for example 1 and 3%)
    • Dyeing Procedure
  • The dyeing beakers filled with dyeing liquor are introduced into the dyeing apparatus, followed by the wool gaberdine on the material-carriers. 5 min at room temperature are followed by heating at 1° C./min to 98° C., dyeing at 98° C. for 60 min, then cooling down to 70° C. and subsequently rinsing with cold water.
    • Aftertreatment
  • The previously rinsed dyeings are aftertreated as follows on the same dyeing apparatus without intervening drying:
  •
    ammonia solution 1 ml/l
    conc. about 25%
    pH 8.5-9.0 (care must be taken to ensure that the pH
    stays in this range during the treatment time)
  • Start at room temperature, heat at full power to 85° C., treat for 20 min, then rinse cold.
    • Evaluation
  • The wool gabardine, now dyed, is evaluated calorimetrically (relative colour strength and residual colour difference).
  • Rating Against Dyeing without Levelling Agent:
  • No colour deepening, slight enhancement of depth of shade (0-25%), distinct enhancement of depth of shade (25-40%), good (40-100%)=
  • *****=excellent
  • ****=very good
  • ***=good
  • **=ok
  • *=poor
  • −=very poor
    • Products Tested: Example 1
  • The utilized active substance (AS) had the following formula:
  • Figure US20090158534A1-20090625-C00003
  • Formulation: 34.5% of AS, 1.08% of C12-15-alcohol with 8 ethylene oxide and 4 propylene oxide units, 0.12% of ethylhexylisononanamide, remainder water.
    • Example 2
  • The same active substance as in Example 1 was used.
  • Formulation: 34.5% of AS, 1.08% of C12-15-alcohol with 8 ethylene oxide and 4 propylene oxide units, 0.12% of ethylhexylisononanamide, 2.0% of cumene sulphonate (40% in water), remainder water.
    • Example 3 Comparative Example
  • The utilized active substance had the following formula where X− is chloride:
  • Figure US20090158534A1-20090625-C00004
  • Formulation: 40% of AS in water
    • Example 4 Comparative Example
  • The active substance utilized was a compound as described in DE-A-2 841 800
    • Summary of Evaluations
  • None 1.0% 3.0%
    1/3 1/1 1/3 1/1 1/3 1/1
    Example 1
    Continuous foam 0 70/10 70/10
    test
    Levelling effect − − **** **** ***** *****
    Skitteriness test none none distinct distinct distinct distinct
    Colour deepening — — slight good none good
    Example 2
    Continuous foam 0 60/5  60/5 
    test
    Levelling effect − − **** **** ***** *****
    Skitteriness test none none distinct distinct distinct distinct
    Colour deepening — — slight good none good
    Example 3
    (comparison)
    Continuous foam 0 >500/>500 >500/>500
    test
    Levelling effect − − *** **** **** *****
    Skitteriness test none none distinct distinct distinct distinct
    Colour deepening — — none good none good
    Example 4
    (comparison)
    Continuous foam 0 >500/>500 >500/>500
    test
    Levelling effect − − *** *** *** ***
    Skitteriness test none none distinct distinct distinct distinct
    Colour deepening — — slight good slight good
  • All inventive examples were better than prior art products.

Claims (9)

1. A process for dyeing a fiber material composed of wool, comprising the step of contacting the fiber material with at least one compound of formula (I)
Figure US20090158534A1-20090625-C00005
wherein
R is singly or doubly unsaturated alkenyl of 12 to 24 carbon atoms,
X− is an anion, and
(n+m) has an average value in the range from 14 to 29.
2. A process according to claim 1, wherein
R is a radical derived from oleic acid, linoleic acid or linolenic acid,
X− is chloride, bromide, iodide, methosulphate, sulphate, phosphate or acetate, and
(n+m) has an average value in the range from 17 to 19.
3. A process according to claim 1,
R is a radical derived from oleic acid.
X− is chloride, and
(n+m) has an average value in the range from 17 to 19.
4. A process according to claim 1, wherein the compound of Formula I is in aqueous solution in the range from 15% to 35% by weight.
5. A process according to claim 4, wherein the concentration of the compound of Formula I is in the aqueous solution is in the range from 25% to 35% by weight and wherein the aqueous solution further comprises 0.1% to 5% by weight of at least one foam-suppressing substance.
6. A process according to claim 1, wherein the contacting step is at a pH in the range from 2 to 9.
7. A process according to claim 1, wherein the liquor ratio of the contacting step is in the range from 2:1 to 80:1 in the case of a batch dyeing and in the range from 5:1 to 500:1 in the case of a continuous dyeing.
8. A process according to claim 1, wherein the liquor ratio of the contacting step is in the range from 5:1 to 30:1 in the case of a batch dyeing and in the range from 20:1 to 300:1 in the case of a continuous dyeing.
9. A fiber material dyed by the process according to claim 1.
US12/083,181 2005-10-07 2006-09-29 Dyeing of Wool Fibres Abandoned US20090158534A1 (en)

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EP05021865A EP1772553A1 (en) 2005-10-07 2005-10-07 Method of dyeing wool fibres
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PCT/EP2006/066875 WO2007042408A1 (en) 2005-10-07 2006-09-29 Dyeing of wool fibres

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CN103669043A (en) * 2013-11-22 2014-03-26 南通市通州区川姜镇盛世王朝家用纺织品设计工作室 Leveling agent for wool and real silk and preparation method thereof
US9840807B2 (en) 2015-03-10 2017-12-12 Charles Francis Luzon Process for dyeing textiles, dyeing and fortifying rubber, and coloring and revitalizing plastics

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TWI558877B (en) * 2015-06-30 2016-11-21 萬能學校財團法人萬能科技大學 A dyeing composition for wool fiber material and using the same method for dyeing process

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103669043A (en) * 2013-11-22 2014-03-26 南通市通州区川姜镇盛世王朝家用纺织品设计工作室 Leveling agent for wool and real silk and preparation method thereof
US9840807B2 (en) 2015-03-10 2017-12-12 Charles Francis Luzon Process for dyeing textiles, dyeing and fortifying rubber, and coloring and revitalizing plastics

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WO2007042408A1 (en) 2007-04-19
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AU2006301364A1 (en) 2007-04-19
CN101278090A (en) 2008-10-01
BRPI0616895A2 (en) 2011-07-05
EP1772553A1 (en) 2007-04-11
ATE532897T1 (en) 2011-11-15
EP1943384B1 (en) 2011-11-09
ES2373459T3 (en) 2012-02-03
AR057538A1 (en) 2007-12-05
KR20080052651A (en) 2008-06-11

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