CA2377658A1 - Process for dyeing or printing polyamide fibres - Google Patents
Process for dyeing or printing polyamide fibres Download PDFInfo
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- CA2377658A1 CA2377658A1 CA002377658A CA2377658A CA2377658A1 CA 2377658 A1 CA2377658 A1 CA 2377658A1 CA 002377658 A CA002377658 A CA 002377658A CA 2377658 A CA2377658 A CA 2377658A CA 2377658 A1 CA2377658 A1 CA 2377658A1
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- Prior art keywords
- dyeing
- dye
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- parts
- compound
- Prior art date
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- Abandoned
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- 238000004043 dyeing Methods 0.000 title claims abstract description 26
- 239000004952 Polyamide Substances 0.000 title claims abstract description 16
- 229920002647 polyamide Polymers 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 239000000758 substrate Substances 0.000 claims abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 150000001412 amines Chemical class 0.000 claims description 9
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 5
- 238000007046 ethoxylation reaction Methods 0.000 claims description 5
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000000975 dye Substances 0.000 description 35
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000835 fiber Substances 0.000 description 9
- 210000002268 wool Anatomy 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 239000007859 condensation product Substances 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 230000005012 migration Effects 0.000 description 5
- 238000013508 migration Methods 0.000 description 5
- 230000035515 penetration Effects 0.000 description 5
- 125000000129 anionic group Chemical group 0.000 description 4
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 0 C*N(CCOS(OC)(=O)=O)C(C)(C)C(C)(C)CC(C)(C)C Chemical compound C*N(CCOS(OC)(=O)=O)C(C)(C)C(C)(C)CC(C)(C)C 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 150000001767 cationic compounds Chemical class 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000010446 mirabilite Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- GNFJBURFXWYRQN-UHFFFAOYSA-M sodium;4-[3-[[2-methyl-4-(4-methylphenyl)sulfonyloxyphenyl]diazenyl]anilino]-3-nitrobenzenesulfonate Chemical compound [Na+].C1=CC(C)=CC=C1S(=O)(=O)OC(C=C1C)=CC=C1N=NC1=CC=CC(NC=2C(=CC(=CC=2)S([O-])(=O)=O)[N+]([O-])=O)=C1 GNFJBURFXWYRQN-UHFFFAOYSA-M 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- -1 aminopropyl Chemical group 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- FTYDFSDLKHVWLD-UHFFFAOYSA-M sodium;3-[[4-[(4-ethoxyphenyl)diazenyl]naphthalen-1-yl]diazenyl]benzenesulfonate Chemical compound [Na+].C1=CC(OCC)=CC=C1N=NC(C1=CC=CC=C11)=CC=C1N=NC1=CC=CC(S([O-])(=O)=O)=C1 FTYDFSDLKHVWLD-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
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
- D06P1/62—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 low-molecular-weight organic compounds with sulfate, sulfonate, sulfenic or sulfinic groups
- D06P1/628—Compounds containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
- C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
- C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
- C07C305/06—Hydrogenosulfates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/334—Polymers modified by chemical after-treatment with organic compounds containing sulfur
-
- 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
- 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
- D06P1/62—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 low-molecular-weight organic compounds with sulfate, sulfonate, sulfenic or sulfinic groups
- D06P1/621—Compounds without nitrogen
- D06P1/627—Sulfates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Coloring (AREA)
- Polyethers (AREA)
Abstract
Claimed is a process for dyeing or printing natural or synthetic polyamides or polyamide-containing compounds with an assistant comprising a compound of formula (I) where the substituents are each as defined in Claim 1, or mixtures thereof, the assistant per se, and the preparation of a storage-stable composition thereof and substrates dyed or printed by the process.
Description
Process for dyeing or printing polyamide fibres This invention relates to a process for dyeing or printing natural and synthetic polyamides or polyamide-containing materials with the aid of an assistant which is characterized by good storage stability.
Levelling assistants are usually surface-active textile dyeing auxiliaries which have the task of thoroughly wetting the fibre/fibre mixture to be dyed, of promoting penetration of the fibres and of preventing too rapid a strike of the dyes, which can lead to unlevelness, during the dyeing process. Suitable levelling assistants are, inter alia, oil sulphonates, fatty alcohol sulphonates, fatty acid condensation products, alkyl and alkylaryl polyglycol ethers and, generally, surface-active substances.
Unlevelnesses are caused by:
~ high and varying affinity of the dye on the fibre ~ high and varying affinity of the fibre for the dye ~ uneven distribution of the dye solution on the fabric ~ temperature differences on the fabric Inadequate levelness can be avoided by suitable dyeing techniques (including improvement of the diffusion of the solution within the fabric, pH control) and by means of levelling assistants.
Levelling assistants primarily reduce the rate of dyeing, increase the rate of dye migration within the fabric and improve the compatibility of the dyes.
Levelling assistants can also have other effects which have no direct influence on the dye-fibre interactions, but nevertheless have a positive effect on the dyeing.
These include the improvement of the 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 to the fibre, or those which have an affinity towards the dye.
Levelling assistants which have an affinity towards the dyes form an addition compound with the dye, the stability of which is dependent on the concentration and normally decreases with increasing temperature.
Levelling assistants are usually surface-active textile dyeing auxiliaries which have the task of thoroughly wetting the fibre/fibre mixture to be dyed, of promoting penetration of the fibres and of preventing too rapid a strike of the dyes, which can lead to unlevelness, during the dyeing process. Suitable levelling assistants are, inter alia, oil sulphonates, fatty alcohol sulphonates, fatty acid condensation products, alkyl and alkylaryl polyglycol ethers and, generally, surface-active substances.
Unlevelnesses are caused by:
~ high and varying affinity of the dye on the fibre ~ high and varying affinity of the fibre for the dye ~ uneven distribution of the dye solution on the fabric ~ temperature differences on the fabric Inadequate levelness can be avoided by suitable dyeing techniques (including improvement of the diffusion of the solution within the fabric, pH control) and by means of levelling assistants.
Levelling assistants primarily reduce the rate of dyeing, increase the rate of dye migration within the fabric and improve the compatibility of the dyes.
Levelling assistants can also have other effects which have no direct influence on the dye-fibre interactions, but nevertheless have a positive effect on the dyeing.
These include the improvement of the 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 to the fibre, or those which have an affinity towards the dye.
Levelling assistants which have an affinity towards the dyes form an addition compound with the dye, the stability of which is dependent on the concentration 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 permits areas of the fabric which have been dyed in a non-level manner to be evened out as a result of dye migration.
Effective levelling assistants have an affinity towards the dye 'which is sufficient to reduce the rate of absorption or to increase the rate of migration.
Differences in the absorption behaviour of different dyes can also be evened out, so that the dyes in a dye mixture strike uniformly.
Assistants with an affinity for dyes can also be used to even out materials which have already been dyed.
Assistants with an affinity towards fibres are absorbed onto the fibre in competition with the dye. This competition reaction reduces the rate of absorption and promotes the rate of migration.
Important dye-affinitive types of levelling assistants for wool are nonionic surfactants or weakly cationic, ethoxylated compounds.
Important fibre-affinitive types of levelling assistants for wool are anionic compounds.
Important dye-affinitive types of levelling assistants for polyamides are nonionic surfactants, cationic compounds or ethoxylated compounds.
Important fibre-affinitive types of levelling assistants for polyamides are cationic compounds.
Levelling assistants are preferably bought, stored and used in an aqueous composition. This presents certain problems particularly for storage. One such problem is creaming, i.e. inhomogeneties in the composition arise, which hinders use without prior treatment.
The aim of the present invention is to provide a process which permits level dyeing or printing with an assistant characterized by excellent storage stability.
Claimed is a process for dyeing or printing natural and synthetic polyamides or polyamide-containing compounds, characterized in that an assistant is used which comprises a compound of the formula (I) ~ ~ O
HsC~N-(CHZ)rt,~- N --~O-~-S-O
O
(0+2) NH4 (I) O=S=O O=S=O
I_ I_ O O
in which n is 12 - 22, the sum a + b +1 is between 20 and 50, preferably between 30 and 40, m is 2 or 3, particularly preferably 3, o is 2 - 5, more preferably 2 or 3, particularly preferably 2, or mixtures thereof.
Also claimed is an assistant for dyeing or printing natural and synthetic polyamides or polyamide-containing materials which comprises a compound of the formula (I) or a mixture thereof.
A preferred assistant has the composition - 60% of a compound of the formula (I) or a mixture thereof and 15 80 - 40% of water.
Compounds or mixtures of the formula (I) are prepared by sulphation of an amino-Cz_6-alkyl-(C,2_22)amine ethoxylate, preferably amino-Cz_3-alkyl-(C,8_Z2)amine ethoxylate having an average degree of ethoxylation of 20 - 50, preferably 30 -20 40, with an excess of sulphamic acid with the addition of a solubilizer, preferably 1-methyl-2-pyrrolidone.
Instead of 1-methyl-2-pyrrolidone, it is possible to use urea or dimethylformamide in particular.
Also claimed is the preparation of a storage-stable composition which comprises a compound according to formula (I) or mixtures thereof, characterized in that amino-C2_6-alkyl-(C~z_22)amine ethoxylate, preferably amino-C2.3-alkyl-(C,8_22)amine ethoxylate having an average degree of ethoxylation of 20 - 50, preferably 30 40, is converted by sulphation with an excess of sulphamic acid with the addition of a solubilizer, and is diluted with water.
Effective levelling assistants have an affinity towards the dye 'which is sufficient to reduce the rate of absorption or to increase the rate of migration.
Differences in the absorption behaviour of different dyes can also be evened out, so that the dyes in a dye mixture strike uniformly.
Assistants with an affinity for dyes can also be used to even out materials which have already been dyed.
Assistants with an affinity towards fibres are absorbed onto the fibre in competition with the dye. This competition reaction reduces the rate of absorption and promotes the rate of migration.
Important dye-affinitive types of levelling assistants for wool are nonionic surfactants or weakly cationic, ethoxylated compounds.
Important fibre-affinitive types of levelling assistants for wool are anionic compounds.
Important dye-affinitive types of levelling assistants for polyamides are nonionic surfactants, cationic compounds or ethoxylated compounds.
Important fibre-affinitive types of levelling assistants for polyamides are cationic compounds.
Levelling assistants are preferably bought, stored and used in an aqueous composition. This presents certain problems particularly for storage. One such problem is creaming, i.e. inhomogeneties in the composition arise, which hinders use without prior treatment.
The aim of the present invention is to provide a process which permits level dyeing or printing with an assistant characterized by excellent storage stability.
Claimed is a process for dyeing or printing natural and synthetic polyamides or polyamide-containing compounds, characterized in that an assistant is used which comprises a compound of the formula (I) ~ ~ O
HsC~N-(CHZ)rt,~- N --~O-~-S-O
O
(0+2) NH4 (I) O=S=O O=S=O
I_ I_ O O
in which n is 12 - 22, the sum a + b +1 is between 20 and 50, preferably between 30 and 40, m is 2 or 3, particularly preferably 3, o is 2 - 5, more preferably 2 or 3, particularly preferably 2, or mixtures thereof.
Also claimed is an assistant for dyeing or printing natural and synthetic polyamides or polyamide-containing materials which comprises a compound of the formula (I) or a mixture thereof.
A preferred assistant has the composition - 60% of a compound of the formula (I) or a mixture thereof and 15 80 - 40% of water.
Compounds or mixtures of the formula (I) are prepared by sulphation of an amino-Cz_6-alkyl-(C,2_22)amine ethoxylate, preferably amino-Cz_3-alkyl-(C,8_Z2)amine ethoxylate having an average degree of ethoxylation of 20 - 50, preferably 30 -20 40, with an excess of sulphamic acid with the addition of a solubilizer, preferably 1-methyl-2-pyrrolidone.
Instead of 1-methyl-2-pyrrolidone, it is possible to use urea or dimethylformamide in particular.
Also claimed is the preparation of a storage-stable composition which comprises a compound according to formula (I) or mixtures thereof, characterized in that amino-C2_6-alkyl-(C~z_22)amine ethoxylate, preferably amino-C2.3-alkyl-(C,8_22)amine ethoxylate having an average degree of ethoxylation of 20 - 50, preferably 30 40, is converted by sulphation with an excess of sulphamic acid with the addition of a solubilizer, and is diluted with water.
The examples below serve to illustrate the invention. Unless stated otherwise, the percentages are by weight, and the degrees are given in Celsius.
Example 1:
100 parts of an aminopropyl (arachidyl/behenyl)amine ethoxylate having an average degree of ethoxylation of 35 are heated to 75°C with stirring in a sulphonation flask fitted with reflux condenser. After 20 parts of sulphamic acid and 2 parts of dimethylformamide have been added, the mixture is heated to 110°C under a nitrogen atmosphere and stirred for a further 12 hours at this temperature. Following cooling to 60°C, 180 parts of demineralized water are added.
This gives a pale brown, clear solution comprising about 40% of a sulphated ethoxylated amine.
Example 2:
The process is as described under Example 1, but instead of 2 parts of dimethylformamide, 2 parts of N-methylpyrrolidone are used.
Example 3:
0.5 part of sodium hydroxide is added to 50 parts of a poly(propyleneamino)-C16/C18-alkylamine, as described, for example, under CAS No. 68-911-79-5.
After the mixture has been heated to 170°C under a nitrogen atmosphere, 100 parts of ethylene oxide are then added. Following cooling to 110°C, 35 parts of urea and 35 parts of sulphamic acid are added, and the mixture is stirred for a further 12 hours at constant temperature. After cooling to 60°C, 330 parts of water are added to the mixture.
This gives a pale brown, clear solution comprising about 40% of a sulphated ethoxylated polyamine.
Example 1:
100 parts of an aminopropyl (arachidyl/behenyl)amine ethoxylate having an average degree of ethoxylation of 35 are heated to 75°C with stirring in a sulphonation flask fitted with reflux condenser. After 20 parts of sulphamic acid and 2 parts of dimethylformamide have been added, the mixture is heated to 110°C under a nitrogen atmosphere and stirred for a further 12 hours at this temperature. Following cooling to 60°C, 180 parts of demineralized water are added.
This gives a pale brown, clear solution comprising about 40% of a sulphated ethoxylated amine.
Example 2:
The process is as described under Example 1, but instead of 2 parts of dimethylformamide, 2 parts of N-methylpyrrolidone are used.
Example 3:
0.5 part of sodium hydroxide is added to 50 parts of a poly(propyleneamino)-C16/C18-alkylamine, as described, for example, under CAS No. 68-911-79-5.
After the mixture has been heated to 170°C under a nitrogen atmosphere, 100 parts of ethylene oxide are then added. Following cooling to 110°C, 35 parts of urea and 35 parts of sulphamic acid are added, and the mixture is stirred for a further 12 hours at constant temperature. After cooling to 60°C, 330 parts of water are added to the mixture.
This gives a pale brown, clear solution comprising about 40% of a sulphated ethoxylated polyamine.
Application Example A
A dyebath consisting of 2000 parts of water 100 parts of wool 1.0 part of the assistants according to the invention consisting of 40% of the formula (I) and 60% of water 1.5 parts of a dye mixture consisting of 85 parts of the dye C.I. Acid Red 404 and 15.0 parts of the dye C.I. Acid Red 399 and 2.0 parts of sodium acetate is adjusted to pH 4.8 using acetic acid and heated to 100°C over the course of 30 minutes. Dyeing takes place at this temperature for 30 minutes. Then, 0.8 part of an anionic naphthalenesulphonic acid/formaldehyde condensation product is slowly added to the dyebath over the course of 15 minutes. The dyeing is then cooled to 60°C, rinsed and dried.
The resulting wool dyeing has an even appearance, excellent penetration and good manufacturing and performance fastnesses.
Application Example B
A dyebath consisting of 2000 parts of water 100 parts of wool 5 parts of Glauber salt, calcined 0.5 part of the assistants according to the invention consisting of 40% of the formula (I) and 60% of water 0.7 part of the dye C.I. Acid Orange 67 1.0 part of the dye C.I. Acid Red 336 and 0.5 part of the dye C.I. Acid Blue 126 is adjusted to pH 5.0 using acetic acid and heated to 100°C over the course of 30 minutes. Dyeing is carried out at this temperature for 30 minutes. Then, 0.5 part of an anionic naphthalenesulphonic acid/formaldehyde condensation product added to the dyebath over the course of 15 minutes, and dyeing is carried out for a further 5 minutes at the boiling temperature. The dyeing is then cooled to 60°C, rinsed and dried.
The resulting wool dyeing has an even appearance, good penetration and good manufacturing and performance fastnesses.
A dyebath consisting of 2000 parts of water 100 parts of wool 1.0 part of the assistants according to the invention consisting of 40% of the formula (I) and 60% of water 1.5 parts of a dye mixture consisting of 85 parts of the dye C.I. Acid Red 404 and 15.0 parts of the dye C.I. Acid Red 399 and 2.0 parts of sodium acetate is adjusted to pH 4.8 using acetic acid and heated to 100°C over the course of 30 minutes. Dyeing takes place at this temperature for 30 minutes. Then, 0.8 part of an anionic naphthalenesulphonic acid/formaldehyde condensation product is slowly added to the dyebath over the course of 15 minutes. The dyeing is then cooled to 60°C, rinsed and dried.
The resulting wool dyeing has an even appearance, excellent penetration and good manufacturing and performance fastnesses.
Application Example B
A dyebath consisting of 2000 parts of water 100 parts of wool 5 parts of Glauber salt, calcined 0.5 part of the assistants according to the invention consisting of 40% of the formula (I) and 60% of water 0.7 part of the dye C.I. Acid Orange 67 1.0 part of the dye C.I. Acid Red 336 and 0.5 part of the dye C.I. Acid Blue 126 is adjusted to pH 5.0 using acetic acid and heated to 100°C over the course of 30 minutes. Dyeing is carried out at this temperature for 30 minutes. Then, 0.5 part of an anionic naphthalenesulphonic acid/formaldehyde condensation product added to the dyebath over the course of 15 minutes, and dyeing is carried out for a further 5 minutes at the boiling temperature. The dyeing is then cooled to 60°C, rinsed and dried.
The resulting wool dyeing has an even appearance, good penetration and good manufacturing and performance fastnesses.
Application Example C
A dyebath consisting of 2000 parts of water 100 parts of wool parts of Glauber salt, calcined 0.5 part of the assistants according to the invention consisting of 40% of the formula (I) and 60% of water 0.7 part of the dye C.I. Acid Orange 67 10 1.0 part of the dye C.I. Acid Red 336 and 0.5 part of the dye C.I. Acid Blue 126 is adjusted to pH 4.5 using acetic acid and heated to 80°C. Dyeing is carried out at this temperature for 30 minutes. Then, 0.5 part of an anionic naphthalenesulphonic acid/formaldehyde condensation product is added to the dyebath, and dyeing is continued for a further 30 minutes. The dyeing is then cooled to 60°C, rinsed and dried.
This gives a brown level wool dyeing with good performance fastnesses and good penetration.
Application Example D
100 parts of polyamide 6 knit are introduced, at 40°C, into a dyebath consisting of 2000 parts of water 0.81 part of the dye C.I. Acid Orange 127 0.13 part of the dye C.I. Acid Red 336 and 0.10 part of the dye C.I. Acid Blue 350 100 parts of wool 2.0 parts of the assistants according to the invention consisting of 40% of the formula (I) and 60% of water.
The dyebath is heated to 98°C over the course of 30 minutes.
Following a migration phase of 30 minutes at 98°C, 0.5 part of an anionic naphthalenesulphonic acid/formaldehyde condensation product is metered into the dyebath over the course of 20 minutes. After further dyeing at 98°C
over the course of 10 minutes, the dyebath is cooled to 80°C over the course of 20 minutes, and the knit is rinsed and dried.
This gives an orange coloration with good penetration of the fibre intersections coupled with complete bath exhaustion.
A dyebath consisting of 2000 parts of water 100 parts of wool parts of Glauber salt, calcined 0.5 part of the assistants according to the invention consisting of 40% of the formula (I) and 60% of water 0.7 part of the dye C.I. Acid Orange 67 10 1.0 part of the dye C.I. Acid Red 336 and 0.5 part of the dye C.I. Acid Blue 126 is adjusted to pH 4.5 using acetic acid and heated to 80°C. Dyeing is carried out at this temperature for 30 minutes. Then, 0.5 part of an anionic naphthalenesulphonic acid/formaldehyde condensation product is added to the dyebath, and dyeing is continued for a further 30 minutes. The dyeing is then cooled to 60°C, rinsed and dried.
This gives a brown level wool dyeing with good performance fastnesses and good penetration.
Application Example D
100 parts of polyamide 6 knit are introduced, at 40°C, into a dyebath consisting of 2000 parts of water 0.81 part of the dye C.I. Acid Orange 127 0.13 part of the dye C.I. Acid Red 336 and 0.10 part of the dye C.I. Acid Blue 350 100 parts of wool 2.0 parts of the assistants according to the invention consisting of 40% of the formula (I) and 60% of water.
The dyebath is heated to 98°C over the course of 30 minutes.
Following a migration phase of 30 minutes at 98°C, 0.5 part of an anionic naphthalenesulphonic acid/formaldehyde condensation product is metered into the dyebath over the course of 20 minutes. After further dyeing at 98°C
over the course of 10 minutes, the dyebath is cooled to 80°C over the course of 20 minutes, and the knit is rinsed and dried.
This gives an orange coloration with good penetration of the fibre intersections coupled with complete bath exhaustion.
Claims (9)
1. Process for dyeing or printing natural and synthetic polyamides or polyamide-containing compounds, characterized in that an assistant is used which comprises a compound of the formula (I) in which n is 18 - 22, the sum a + b + 1 is between 20 and 50, m is 2 or 3, o is 2-5, or mixtures thereof.
2. Process according to Claim 1, characterized in that, in the formula (I), the sum a + b + 1 is between 30 and 40, m is 3, and o is 2 or 3.
3. Process according to Claim 1 or 2, characterized in that in the formula (I) o is 2.
4. Assistant for dyeing or printing natural and synthetic polyamides or polyamide-containing materials, characterized in that it comprises a compound of the formula (I) according to Claims 1 to 3 or a mixture thereof.
5. Assistant according to Claim 4, characterized in that it comprises 20 - 60%
of a compound of the formula (I) or a mixture thereof.
of a compound of the formula (I) or a mixture thereof.
6. Preparation of a storage-stable composition which comprises a compound according to formula (I) or mixtures thereof, characterized in that an amino-C2-6-alkyl-(C12-22)amine ethoxylate, preferably an amino-C2-3-alkyl-(C18-22)amine ethoxylate having an average degree of ethoxylation of 20 -50, preferably 30 - 40, is converted by sulphation with an excess of sulphamic acid with the addition of a solvent, preferably 1-methyl-2-pyrrolidone, and is diluted with water.
7. Preparation of a storage-stable composition according to Claim 6, characterized in that an amino-C2-3-alkyl-(C18-22)amine ethoxylate having an average degree of ethoxylation of 30 - 40 is used.
8. Preparation of a storage-stable composition according to Claim 6 or 7, characterized in that 1-methyl-2-pyrrolidone is used as solubilizer.
9. Substrate dyed by a process according to one of Claims 1 to 3.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH142599 | 1999-08-03 | ||
| CH1425/99 | 1999-08-03 | ||
| PCT/IB2000/001053 WO2001009430A1 (en) | 1999-08-03 | 2000-07-28 | Process for dyeing or printing polyamide fibres |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2377658A1 true CA2377658A1 (en) | 2001-02-08 |
Family
ID=4210170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002377658A Abandoned CA2377658A1 (en) | 1999-08-03 | 2000-07-28 | Process for dyeing or printing polyamide fibres |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP1208264A1 (en) |
| JP (1) | JP2003506583A (en) |
| CN (1) | CN1364206A (en) |
| CA (1) | CA2377658A1 (en) |
| MX (1) | MXPA02000830A (en) |
| WO (1) | WO2001009430A1 (en) |
| ZA (1) | ZA200110489B (en) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3919283A (en) * | 1965-03-18 | 1975-11-11 | Ciba Geigy Ag | Sulfate derivatives of polyglycol compounds |
| CH478951A (en) * | 1967-07-07 | 1969-06-13 | Ciba Geigy | Process for dyeing wool with 1: 2 metal complex dyes |
| FR2574791A1 (en) * | 1984-12-14 | 1986-06-20 | Sandoz Sa | FATTY AMINO ACID SULFATES, THEIR PREPARATION AND THEIR USE AS AUXILIARY PRODUCTS |
| DE3837199A1 (en) * | 1987-11-13 | 1989-05-24 | Sandoz Ag | Use of amino-alkylene oxide adducts as leather dyeing auxiliaries |
-
2000
- 2000-07-28 WO PCT/IB2000/001053 patent/WO2001009430A1/en not_active Application Discontinuation
- 2000-07-28 JP JP2001513681A patent/JP2003506583A/en active Pending
- 2000-07-28 CA CA002377658A patent/CA2377658A1/en not_active Abandoned
- 2000-07-28 MX MXPA02000830A patent/MXPA02000830A/en unknown
- 2000-07-28 CN CN 00810804 patent/CN1364206A/en active Pending
- 2000-07-28 EP EP00948190A patent/EP1208264A1/en not_active Withdrawn
-
2001
- 2001-12-20 ZA ZA200110489A patent/ZA200110489B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA200110489B (en) | 2003-03-20 |
| MXPA02000830A (en) | 2002-10-23 |
| EP1208264A1 (en) | 2002-05-29 |
| JP2003506583A (en) | 2003-02-18 |
| WO2001009430A1 (en) | 2001-02-08 |
| CN1364206A (en) | 2002-08-14 |
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| Date | Code | Title | Description |
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| FZDE | Discontinued |