EP0305839B1 - Procédé de teinture de fibres cellulosiques - Google Patents
Procédé de teinture de fibres cellulosiques Download PDFInfo
- Publication number
- EP0305839B1 EP0305839B1 EP88113606A EP88113606A EP0305839B1 EP 0305839 B1 EP0305839 B1 EP 0305839B1 EP 88113606 A EP88113606 A EP 88113606A EP 88113606 A EP88113606 A EP 88113606A EP 0305839 B1 EP0305839 B1 EP 0305839B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- added
- dye
- process according
- alkyl
- amine
- 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 18
- 238000004043 dyeing Methods 0.000 title claims description 13
- 239000000975 dye Substances 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000000982 direct dye Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 229920003043 Cellulose fiber Polymers 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000003792 electrolyte Substances 0.000 claims description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000003827 glycol group Chemical group 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 230000004087 circulation Effects 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- -1 naphthyl radicals Chemical class 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000000985 reactive dye Substances 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000003008 phosphonic acid esters Chemical class 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- 238000010016 exhaust dyeing Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000002960 margaryl 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])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- 125000002958 pentadecyl 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])[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 125000004079 stearyl 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])[H] 0.000 description 1
- 239000000979 synthetic dye Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000009970 yarn dyeing 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
- D06P1/60—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
Definitions
- Cycloalkyl stands in particular for cyclopentyl, cyclohexyl, tetra- or decahydronaphthyl and their derivatives substituted by C1-C12-alkyl.
- Suitable aryl radicals are, for example, the phenyl and naphthyl radicals and their derivatives substituted by halogen, C6-C12-alkyl, cyclohexyl or phenyl-C1-C3-alkyl.
- Aralkyl is preferably benzyl or phenylethyl substituted by C5-C12-alkyl.
- radicals R in formula (I) the dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, eikosyl and behenyl radicals.
- Suitable anions X ⁇ are conventional inorganic or organic anions, for example chloride, bromide, iodide, methosulfate, sulfate, phosphate or acetate.
- Preferred compounds of the formula (I) are compounds of the formula wherein R 'for C12-C22 alkyl, R ' 1 for hydrogen, methyl, ethyl, benzyl or R ' 3rd For and R ' 4th represent methylene, ethylene or phenylene, and R2, X ⁇ , x, y, and z have the meaning given in formula (I).
- the compounds (I) are prepared by known processes.
- cellulose in particular with direct dyes, which e.g. in Color Index 3rd Edition (1971), Vol. 2, pp. 2007-2477, and with reactive dyes, e.g. in "The Chemistry of Synthetic Dyes” (K. Venkataraman), Vol. VI (1972).
- auxiliaries mentioned is particularly advantageous when dyeing with direct dyes and in particular if salt is added before the dye is added (“all-in” process).
- Salt here means the electrolyte, the addition of which is customary to increase the color yield, preferably sodium sulfate or sodium chloride.
- the drawing up of direct dyes is usually controlled by the addition of salt in the case of exhaust dyeing processes. You start at a low temperature and without the addition of salt in order to prevent it from being drawn up too quickly and the resulting irregularity. Only at the final temperature is salt added, usually in portions, in order to gradually exhaust the dye bath. This is a complex way of working.
- EP-A2-0 141 078 describes a process by which it is possible, by adding an ester group-containing saponifiable leveling agent, to dye according to an "all-in" process, without additional migration time and without impairing the dye yield.
- a disadvantage of the leveling agents containing ester groups is their limited shelf life. It has now surprisingly been found that the amines (I) are suitable for this process. The amines (I) are stable in storage. They slow down the absorption of the dyes at temperatures below 40 ° C and neutral to weakly acidic pH values. In contrast, hardly any dye is retained at higher temperatures and neutral to alkaline pH values.
- the salt is added to the dyebath before the dye.
- the leveling agent is added before or together with the dye.
- the amount of leveling agent is generally between 0.1 and 2%, based on the weight of the textile to be dyed. It is set so that the The initial rate of bath exhaustion is in a certain range, which is based on the requirements for equality, the goods, the system, the shade and the dyes.
- the permissible range is generally 20 to 60% bath exhaustion in the first 10 minutes; preferably it is between 20 and 40% per 10 minutes. It is particularly advantageous to start dyeing at a low temperature, preferably between 25 and 40 ° C. From 70 ° C you can heat quickly.
- the initial pH should be between 5.5 and 7.5. If necessary, the dye yield can be increased at the end of the dyeing process by making the pH alkaline (above 8).
- the leveling agents (I) are preferably suitable for dyeing with reactive dyes if salt is added from the beginning, but alkali is added later.
- the procedure is similar to that of direct dyes. You start at low temperature and neutral to weakly acidic pH. The aid prevents the dyes from being absorbed too quickly in the presence of salt. Then, as usual, the pH is changed and / or heated by adding alkali. This means that the salt can be added at the beginning, even under critical conditions, and the time-consuming and time-consuming metering in can be avoided.
- the material carrier is then retracted. After 10 minutes of liquor circulation from the inside to the outside at 40 ° C with 1 ° C / min. heated to 98 ° C. The fleet alternately circulates 10 minutes from the inside out and 5 minutes from the outside in. After 30 minutes at 98 ° C at 2 ° C / min. cooled to 80 ° C. After the liquor has been drained, the coils are dried. A level, light beige coloration is obtained.
- a package of 700 g bleached cotton yarn is dyed in a laboratory package as follows: 11 l of dye liquor from softened water at 20 ° C and with a pH of 6.5 are added: 3.5 g of the auxiliary from example 2, 11 g of a wetting agent based on phosphonic acid esters and 300 g sodium chloride.
- the dye liquor is pumped into the apparatus. After 5 minutes of circulation with 2 circulations / min from the inside to the outside through the coil, 3.5 g of the pre-dissolved reactive dye added over the batch vessel.
- the mixture is heated to 40 ° C. within 30 minutes, then 22 g of soda calc. and after a further 30 min, 11 ml of NaOH 38 ° Be added via the batch container. After a further 30 minutes, the dye liquor is drained off and rinsed as usual. The result is a level red color.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Claims (6)
- Procédé de teinture discontinue de fibres cellulosiques en présence d'amines contenant des groupes éther de glycol, dans lequel on effectue l'addition classique d'électrolyte avant l'addition de colorant, caractérisé en ce qu'on utilise comme amines portant des groupes glycol des composés de formule
R est un groupe alkyle en C₁₂ à C₂₂, cycloalkyle, aryle ou aralkyle ayant chacun 12 à 22 atomes de carbone,R₁ est l'hydrogène, un groupe alkyle en C₁ à C₄, benzyle ou
R₂ est l'hydrogène ou le groupe méthyle,R₃ est un groupe
R₄ est un groupe arylène ayant 6 à 18 atomes de carbone ou alkylène en C₁ à C₁₇,x, y et z représentent un nombre entier de 1 à 20, la somme x + y + z devant avoir une valeur de 5 à 20, etX⊖ est un anion,sous réserve qu'au moins 80 % des motifs oxyde d'alkylène contenus dans la molécule soient des motifs oxyde d'éthylène. - Procédé suivant la revendication 1, caractérisé en ce qu'on utilise comme amines des composés de formule
R' est un groupe alkyle en C₁₂ à C₂₂,R'₁ est l'hydrogène, un groupe méthyle, éthyle, benzyle ou
R'₃ est un groupe
R'₄ est un groupe méthylène, éthylène ou phénylène, etR₂, X⊖, x, y et z ont la définition indiquée pour la formule (I). - Procédé suivant la revendication 1, caractérisé en ce qu'on ajoute un sel au bain de teinture avant l'addition du colorant et de l'amine.
- Procédé suivant la revendication 1, caractérisé en ce qu'on ajoute l'amine au bain de teinture soit avant le colorant, soit en même temps que lui.
- Procédé suivant la revendication 1, caractérisé en ce qu'on utilise l'amine en une quantité de 0,1 à 2 % en poids par rapport à la fibre cellulosique.
- Procédé suivant la revendication 1, caractérisé en ce qu'on effectue la teinture avec des colorants directs et on choisit la quantité d'amines de manière que l'épuisement du bain se situe entre 20 et 60 % dans les dix premières minutes.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19873729459 DE3729459A1 (de) | 1987-09-03 | 1987-09-03 | Verfahren fuer das faerben von cellulosefasern |
| DE3729459 | 1987-09-03 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0305839A2 EP0305839A2 (fr) | 1989-03-08 |
| EP0305839A3 EP0305839A3 (fr) | 1991-09-11 |
| EP0305839B1 true EP0305839B1 (fr) | 1993-11-10 |
Family
ID=6335143
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP88113606A Expired - Lifetime EP0305839B1 (fr) | 1987-09-03 | 1988-08-22 | Procédé de teinture de fibres cellulosiques |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0305839B1 (fr) |
| JP (1) | JPH0197283A (fr) |
| DE (2) | DE3729459A1 (fr) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH438169A4 (fr) * | 1969-03-24 | 1974-02-28 | ||
| US3591325A (en) * | 1969-04-25 | 1971-07-06 | Arkansas Co Inc | Products and process for removing organic pigments and dyes from dyed and printed natural and synthetic textile materials |
| BE754502A (fr) * | 1969-08-07 | 1971-01-18 | Bayer Ag | Procede de teinture de matieres fibreuses azotees |
| DE3329445A1 (de) * | 1983-08-16 | 1985-03-07 | Bayer Ag, 5090 Leverkusen | Verfahren zum faerben von cellulosefasern |
| DE3700674A1 (de) * | 1986-01-15 | 1987-07-16 | Ciba Geigy Ag | Verfahren zum bedrucken von cellulosischen fasermaterialien |
-
1987
- 1987-09-03 DE DE19873729459 patent/DE3729459A1/de not_active Withdrawn
-
1988
- 1988-08-22 DE DE88113606T patent/DE3885549D1/de not_active Expired - Fee Related
- 1988-08-22 EP EP88113606A patent/EP0305839B1/fr not_active Expired - Lifetime
- 1988-09-01 JP JP63216426A patent/JPH0197283A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE3729459A1 (de) | 1989-03-16 |
| DE3885549D1 (de) | 1993-12-16 |
| EP0305839A3 (fr) | 1991-09-11 |
| EP0305839A2 (fr) | 1989-03-08 |
| JPH0197283A (ja) | 1989-04-14 |
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