EP1943384A1 - Dyeing of wool fibres - Google Patents

Dyeing of wool fibres

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Publication number
EP1943384A1
EP1943384A1 EP06793903A EP06793903A EP1943384A1 EP 1943384 A1 EP1943384 A1 EP 1943384A1 EP 06793903 A EP06793903 A EP 06793903A EP 06793903 A EP06793903 A EP 06793903A EP 1943384 A1 EP1943384 A1 EP 1943384A1
Authority
EP
European Patent Office
Prior art keywords
dyeing
range
process according
active substance
wool
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP06793903A
Other languages
German (de)
French (fr)
Other versions
EP1943384B1 (en
Inventor
Manfred Jungen
Jean-Pierre Vierling
Udo Schmitt
Rino Marazzi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Clariant Finance BVI Ltd
Original Assignee
Clariant International Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Clariant International Ltd filed Critical Clariant International Ltd
Priority to EP06793903A priority Critical patent/EP1943384B1/en
Publication of EP1943384A1 publication Critical patent/EP1943384A1/en
Application granted granted Critical
Publication of EP1943384B1 publication Critical patent/EP1943384B1/en
Not-in-force legal-status Critical Current
Anticipated expiration legal-status Critical

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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 poly glycol 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)
  • 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.
  • 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.
  • the active substance is a compound of formula (II)
  • (n+m) has an average value in the range from 17 to 19.
  • 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.
  • 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.
  • 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 sulp hated 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.
  • biocides if desired or necessary dispersing assistants or wetting agents, for example sulphonated or sulp hated 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.
  • 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.
  • 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 1 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 1/min.
  • 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/1 in 2° Be-NaOH solution in demineralized water, with 2° Be-NaOH being equivalent to 12 g/1 NaOH solid or 30 ml/1 of 36°Be NaOH.
  • the test temperature is in the range from 20 to 25°C.
  • 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.
  • Dyeing was carried out using various concentrations (1/3 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.
  • 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.
  • Glauber salt calc. 5 5 %
  • Acetic acid pH 5 5 x without and with increasing amounts of levelling agent (for example 1 and 3%)
  • 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 0 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.
  • Glauber salt calc. 5 5 %
  • 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 l°C/min to 98°C, dyeing at 98°C for 60 min, then cooling down to 70 0 C and subsequently rinsing with cold water.
  • 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.
  • Glauber salt calc. 5 5 %
  • Acetic acid pH 5 5 x without and with increasing amounts of levelling agent (for example 1 and 3%)
  • 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 l°C/min to 98°C, dyeing at 98°C for 60 min, then cooling down to 70 0 C and subsequently rinsing with cold water.
  • the wool gaberdine, now dyed, is evaluated colorimetrically (relative colour strength and residual colour difference).
  • the utilized active substance (AS) had the following formula:
  • Formulation 34.5% of AS, 1.08% of Ci 2- i 5 -alcohol with 8 ethylene oxide and 4 propylene oxide units, 0.12% of ethylhexylisononanamide, remainder water.
  • Formulation 34.5% of AS, 1.08 % of Ci 2 -i 5 -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 SUMMARY OF EVALUATIONS

Landscapes

  • 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 guaternized fatty acid amine, preferably a quaternized, unsaturated oleylamine, is used as a levelling agent. The present compound leads to very uniform dyeings and is very effective in low concentrations.

Description

DYEING OF WOOL FIBRES
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 poly glycol 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)
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)
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 sulp hated 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 Ci2-i5-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 1 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 1/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/1 in 2° Be-NaOH solution in demineralized water, with 2° Be-NaOH being equivalent to 12 g/1 NaOH solid or 30 ml/1 of 36°Be 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: 2g/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 1 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 1/min.kg = 1/3 circulation/min)
Dye
Dyeing was carried out using various concentrations (1/3 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.
Dyemg liquor Levelling agent X X %
Glauber salt calc. 5 5 %
Sodium acetate cryst. 1 1 g/i
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 700C 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 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. 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/ 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 l°C/min to 98°C, dyeing at 98°C for 60 min, then cooling down to 700C 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 cone, about 25% 1 ml/1 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/i
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 l°C/min to 98°C, dyeing at 98°C for 60 min, then cooling down to 700C 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 cone, about 25% 1 ml/1 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 gaberdine, now dyed, is evaluated colorimetrically (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:
Formulation: 34.5% of AS, 1.08% of Ci2-i5-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 Ci2-i5-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:
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
All inventive examples were better than prior art products.

Claims

1. Process for dyeing fibre materials composed of wool, characterized in that one or more compounds of formula (I)
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.
2. 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. Process according to Claim 2 wherein the active substance is a compound of formula (II)
where
(n+m) has an average value in the range from 17 to 19.
4. Process according to at least one of the preceding claims, characterized in that 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.
5. Process according to Claim 4, characterized in that the concentration of active substance in the aqueous solution is in the range from 25% to 35% by weight and in that 0.1% to 5% by weight of foam-suppressing substances are included as further additives.
6. Process according to any one of Claims 1 to 5, characterized in that dyeing is effected at a pH in the range from 2 to 9.
7. Process according to any one of Claims 1 to 6, characterized in that the liquor ratio 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. Process according to Claim 7, characterized in that the liquor ratio 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.
EP06793903A 2005-10-07 2006-09-29 Dyeing of wool fibres Not-in-force EP1943384B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP06793903A EP1943384B1 (en) 2005-10-07 2006-09-29 Dyeing of wool fibres

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP05021865A EP1772553A1 (en) 2005-10-07 2005-10-07 Method of dyeing wool fibres
PCT/EP2006/066875 WO2007042408A1 (en) 2005-10-07 2006-09-29 Dyeing of wool fibres
EP06793903A EP1943384B1 (en) 2005-10-07 2006-09-29 Dyeing of wool fibres

Publications (2)

Publication Number Publication Date
EP1943384A1 true EP1943384A1 (en) 2008-07-16
EP1943384B1 EP1943384B1 (en) 2011-11-09

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Application Number Title Priority Date Filing Date
EP05021865A Withdrawn EP1772553A1 (en) 2005-10-07 2005-10-07 Method of dyeing wool fibres
EP06793903A Not-in-force EP1943384B1 (en) 2005-10-07 2006-09-29 Dyeing of wool fibres

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EP05021865A Withdrawn EP1772553A1 (en) 2005-10-07 2005-10-07 Method of dyeing wool fibres

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US (1) US20090158534A1 (en)
EP (2) EP1772553A1 (en)
KR (1) KR20080052651A (en)
CN (1) CN101278090B (en)
AR (1) AR057538A1 (en)
AT (1) ATE532897T1 (en)
AU (1) AU2006301364A1 (en)
BR (1) BRPI0616895A2 (en)
ES (1) ES2373459T3 (en)
PE (1) PE20070732A1 (en)
WO (1) WO2007042408A1 (en)

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CN103669043B (en) * 2013-11-22 2015-10-28 南通市通州区川姜镇盛世王朝家用纺织品设计工作室 Wool real silk levelling agent 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
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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US3104931A (en) * 1958-03-11 1963-09-24 Ciba Geigy Corp Process for dyeing wool
CH373012A (en) * 1961-05-24 1963-07-31 Geigy Ag J R Process for the production of real wool dyeings with copper or nickel phthalocyanines
YU32071B (en) * 1963-10-04 1974-04-30 Ciba Geigy Ag Postopek za barvanje volne
US3816529A (en) * 1969-05-16 1974-06-11 American Cyanamid Co N-carbamoylethyl aromatic amine compounds
DE3368956D1 (en) * 1982-09-03 1987-02-12 Ciba Geigy Ag Dyeing auxiliary and its use in dyeing or printing synthetic polyamide fibres

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Title
See references of WO2007042408A1 *

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WO2007042408A1 (en) 2007-04-19
CN101278090B (en) 2011-10-19
CN101278090A (en) 2008-10-01
AR057538A1 (en) 2007-12-05
BRPI0616895A2 (en) 2011-07-05
EP1943384B1 (en) 2011-11-09
US20090158534A1 (en) 2009-06-25
ES2373459T3 (en) 2012-02-03
KR20080052651A (en) 2008-06-11
AU2006301364A1 (en) 2007-04-19
ATE532897T1 (en) 2011-11-15
EP1772553A1 (en) 2007-04-11
PE20070732A1 (en) 2007-08-24

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