EP0601971B1 - Procédé de teinture ou d'impression par trichromie - Google Patents
Procédé de teinture ou d'impression par trichromie Download PDFInfo
- Publication number
- EP0601971B1 EP0601971B1 EP93810813A EP93810813A EP0601971B1 EP 0601971 B1 EP0601971 B1 EP 0601971B1 EP 93810813 A EP93810813 A EP 93810813A EP 93810813 A EP93810813 A EP 93810813A EP 0601971 B1 EP0601971 B1 EP 0601971B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- dye
- formula
- hydrogen
- dyeing
- 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
- 0 CC1(C)C(C(*)=CC)=CC(C)=CC1 Chemical compound CC1(C)C(C(*)=CC)=CC(C)=CC1 0.000 description 4
- DTRJDURRPWBDEY-HKOLQMFGSA-N Cc(c(/N=N\c(cc1)ccc1S(O)(=O)=O)c1)cc(/N=N\c(cc2)ccc2OC)c1OC Chemical compound Cc(c(/N=N\c(cc1)ccc1S(O)(=O)=O)c1)cc(/N=N\c(cc2)ccc2OC)c1OC DTRJDURRPWBDEY-HKOLQMFGSA-N 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
- 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
- D06P3/16—Wool using acid dyes
-
- 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
- D06P3/24—Polyamides; Polyurethanes
- D06P3/241—Polyamides; Polyurethanes using acid dyes
-
- 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
- D06P3/82—Textiles which contain different kinds of fibres
- D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
- D06P3/8209—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing amide groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/916—Natural fiber dyeing
- Y10S8/917—Wool or silk
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/924—Polyamide fiber
Definitions
- the present invention relates to a process for trichromatic dyeing or printing of natural and synthetic polyamide fiber materials with at least one blue-coloring, sulfo-containing anthraquinone dye, at least one red-dyeing azo dye and at least one yellow-colored or orange-dyeing azo dye.
- the object underlying the present invention was to find a process for dyeing or printing natural and synthetic polyamide fiber materials with dyes suitable for combination according to the trichromatic principle.
- the dyeings obtained in this way fulfill the tasks set.
- the dyeings obtained are distinguished by a uniform color structure with constant shade in different concentrations and good combinability.
- the present invention relates to a process for trichromatic dyeing or printing of natural or synthetic polyamide fiber materials, which is characterized in that at least one blue-coloring anthraquinone dye of the formula wherein R 1 , R 2 , R 3 and R 4 are independently hydrogen or C 1 -C 6 alkyl, wherein the sum of the carbon atoms of the radicals R 1 , R 2 , R 3 and R 4 is the number 4, 5 or 6 and the sulfo group in the anthraquinone dye of the formula (1) is bonded in the designated 6 or 7 position, together with at least one red-coloring dye of the formula wherein R 5 is phenyl or cyclohexyl and R 6 is C 1 -C 4 alkyl, or the radicals R 5 and R 6 together with the nitrogen atom connecting them form an azepinyl ring, and at least one of the yellow or orange-colored dyes of the formulas (3) , (4) and (5) wherein R 7 , R 8 and R 10
- Trichromatic is to be understood as the additive color mixture of suitably selected yellow or orange, red and blue coloring dyes, with which any desired shade of the visible color spectrum can be adjusted by a suitable choice of the proportions of the dyes.
- C 1 -C 6 alkyl for R 1 , R 2 , R 3 and R 4 in formula (1) are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl and straight-chain or branched pentyl or hexyl.
- the C 1 -C 4 alkyl radicals are preferred.
- the anthraquinone dyes of the formula (1) are generally used as mixtures of isomers, the individual isomers differing only in the sulfo group bonded in the 6- or 7-position; however, the individual isomers can also be used as individual dyes.
- R 6 , R 7 , R 8 , R 9 , R 10 , B 1 , B 2 , E 1 , X, W 2 and W 3 are methyl, ethyl, propyl, isopropyl, butyl , Isobutyl, sec-butyl or tert-butyl.
- R 7 , R 8 , R 10 , B 1 , B 2 , E 1 and W 2 for example methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy or tert. -Butoxy into consideration.
- Examples of suitable C 2 -C 4 alkanoylamino for R 7 , R 8 and R 10 are acetylamino, propionylamino or butyrylamino, in particular acetylamino.
- Halogen R 7 , R 8 , R 10 and W 2 are, for example, fluorine or bromine and in particular chlorine.
- C 2 -C 4 -hydroxyalkyl radical for X is a straight-chain or branched hydroxyalkyl radical, such as the ⁇ -hydroxyethyl, ⁇ -hydroxypropyl, ⁇ -hydroxybutyl or the ⁇ -ethyl- ⁇ -hydroxyethyl radical.
- W 4 is a C 1 -C 8 -alkyl radical, it is, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, and straight-chain or branched pentyl, hexyl, heptyl or octyl.
- W 1 as phenylsulfonyl and W 3 as phenyl can be unsubstituted in the phenyl ring or by C 1 -C 4 alkyl, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl, C 1 -C 4 -alkoxy, such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy or tert-butoxy, or substituted by halogen, such as fluorine, bromine or especially chlorine.
- C 1 -C 4 alkyl such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl
- C 1 -C 4 -alkoxy such as methoxy, ethoxy, propoxy, isopropoxy, butoxy
- Preferred anthraquinone dyes of the formula (1) are those in which R 2 and R 3 are independently methyl or ethyl and R 4 is hydrogen or methyl.
- the radical R 1 in the anthraquinone dye of the formula (1) is preferably isopropyl or sec-butyl, in particular isopropyl.
- Anthraquinone dyes of the formula (1) in which R 1 is isopropyl, R 2 and R 3 are independently methyl or ethyl and R 4 is hydrogen or methyl are particularly preferred for the process according to the invention.
- the sum of the carbon atoms of the radicals R 1 , R 2 , R 3 and R 4 in the anthraquinone dye of the formula (1) is preferably the number 5.
- Anthraquinone dyes of the formula (1) in which R 1 is isopropyl, R 2 and R 3 are methyl and R 4 is hydrogen are very particularly preferred.
- a dye of the formula is preferably used as the red-coloring dye of the formula (2) or in particular a dye of the formula (6) or (7) and preferably a dye of the formula (6).
- the yellow or orange coloring dyes of the formula (3) are preferably dyes containing sulfo groups.
- W 1 is phenylsulfonyl
- W 2 is hydrogen, halogen or C 1 -C 4 -alkyl
- W 3 is optionally C 1 -C 4 -alkyl
- W 4 is hydrogen, in particular the dye of the formula
- a dye of the formula (3) in which R 7 is hydrogen, R 8 and R 9 are C 1 -C 4 -alkyl, R 10 is sulfo and n is the number 1, or a dye of formula (4) wherein B 1 and B 2 are independently C 1 -C 4 alkyl or C 1 -C 4 alkoxy, E 1 is hydrogen and XC 1 -C 4 alkyl, or a dye of Formula (5), in which W 1 is phenylsulfonyl, W 2 is hydrogen, halogen or C 1 -C 4 -alkyl, W 3 is phenyl which is optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or halogen and W 4 Is hydrogen.
- an anthraquinone dye of the formula (1) is used together with a red-coloring dye of the formula (6) or (7) and a yellow or orange-coloring dye of the formula (9) or (11), where the meanings and preferences given above apply to the anthraquinone dye of the formula (1).
- the present invention further provides dye mixtures which comprise at least one anthraquinone dye of the formula (1) together with at least one red-dyeing dye of the formula (2) and at least one yellow or orange-dyeing dye of the formulas (3), (4) and (5 ) contain.
- the meanings and preferences given above apply to the dyes of the formulas (1), (2), (3), (4) and (5).
- the dyes of the formulas (1), (2), (3), (4) and (5) used in the process according to the invention for trichromatic dyeing or printing are known or can be prepared analogously to known dyes.
- the anthraquinone dyes are obtained analogously to the information in GB-A-1,438,354.
- the dyes used in the process according to the invention for trichromatic dyeing or printing are either in the form of their free sulfonic acid or, preferably, as their salts.
- suitable salts are the alkali, alkaline earth or ammonium salts or the salts of an organic amine.
- suitable salts include the sodium, lithium, potassium or ammonium salts or the salt of mono-, di- or triethanolamine.
- the dyes used in the process according to the invention can contain further additives such as e.g. Table salt or dextrin included.
- the process according to the invention for trichromatic dyeing or printing can be applied to the customary dyeing or printing processes.
- the dyeing liquors or printing pastes can contain other additives, for example wetting agents, anti-foaming agents, leveling agents or agents which influence the property of the textile material, such as e.g. Plasticizers, flame retardants or dirt, water and oil repellents, water softeners and natural or synthetic thickeners such as Alginates and cellulose ethers.
- the process according to the invention for trichromatic dyeing or printing is also for dyeing from short liquors, such as e.g. suitable for continuous dyeing processes or discontinuous and continuous foam coloring processes.
- the dyes used in the process according to the invention are distinguished in trichromatic dyeing or printing by uniform color build-up, good absorption behavior, good constancy of shades even in different concentrations, good fastness properties and in particular by very good combinability.
- the process according to the invention for trichromatic dyeing or printing is suitable for dyeing or printing both natural polyamide materials such as wool, as in particular of synthetic polyamide materials, such as polyamide 6 or polyamide 6.6, and is suitable for dyeing or printing wool and synthetic polyamide blended fabrics or yarns.
- the textile material mentioned can be in a wide variety of processing forms, such as as fiber, yarn, woven or knitted fabric and in particular in the form of carpets.
- parts represent parts by weight.
- the temperatures are degrees Celsius.
- the relationship between parts by weight and parts by volume is the same as that between grams and cubic centimeters.
- the dyeing time at a temperature of 98 ° C is 30 to 90 minutes.
- the dyed polyamide fiber material is then removed and rinsed and dried as usual.
- a piece of fabric dyed in a brown shade that does not have any streakiness due to the material is obtained.
- the anthraquinone dyes of the formulas (101), (104), (105) and (106) listed in the above examples are each used as isomer mixtures, the individual isomers differing only in the position of the sulfo group in the 6- or 7-position; the mixing ratio of the two isomers is approximately 1: 1.
- the individual isomers can also be used as individual dyes.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Claims (12)
- Procédé de teinture ou d'impression en trichromie de matériaux fibreux en polyamide naturel ou synthétique, caractérisé en ce que l'on utilise au moins un colorant anthraquinonique bleu de formule
en conjonction avec au moins un colorant rouge de formule
et au moins un des colorants jaunes ou oranges de formule (3), (4) et (5) - Procédé conforme à la revendication 1, caractérisé en ce que l'on utilise un colorant anthraquinonique de formule (1) dans lequel R2 et R3 représentent, indépendamment l'un de l'autre un groupe méthyle ou éthyle et R4 est un atome d'hydrogène ou un groupe méthyle.
- Procédé conforme à une des revendications 1 et 2, caractérisé en ce que l'on utilise un colorant anthraquinonique de formule (1) dans lequel R1 est un groupe isopropyle ou sec-butyle, en particulier un groupe isopropyle.
- Procédé conforme à une des revendications 1 à 3, caractérisé en ce que l'on utilise un colorant anthraquinonique de formule (1) dans lequel R1 est un résidu isopropyle, R2 et R3 représentent, indépendamment l'un de l'autre, un groupe méthyle ou éthyle et R4 est un atome d'hydrogène ou un groupe méthyle.
- Procédé conforme à une des revendications 1 à 4, caractérisé en ce que l'on utilise un colorant anthraquinonique de formule (1) dans lequel la somme des atomes de carbone des résidus R1, R2, R3 et R4 vaut 5.
- Procédé conforme à la revendication 6, caractérisé en ce que l'on utilise, comme colorant rouge, un colorant de formule (6) ou (7), en particulier un colorant de formule (6).
- Procédé conforme à une des revendications 1 à 7, caractérisé en ce que l'on utilise, comme colorant jaune ou orange, un colorant de formule (3) ) dans lequel R7 est un atome d'hydrogène, R8 et R9 sont des résidus alkyle en C1-4, R10 est un groupe sulfo et n vaut 1, ou un colorant de formule (4) où B1 et B2 représentent, indépendamment l'un de l'autre, un résidu alkyle en C1-4 ou alcoxy en C1-4, E1 est un atome d'hydrogène et X un groupe alkyle en C1-4, ou encore un colorant de formule (5) où W1 est un groupe phénylsulfonyle, W2 est un atome d'hydrogène ou d'halogène ou un groupe alkyle en C1-4, W3 est un groupe phényle pouvant porter, comme substituant, un résidu alkyle en C1-4, alcoxy en C1-4 ou un atome d'halogène et W4 est un atome d'hydrogène.
- Procédé conforme à une des revendications 1 à 9, caractérisé en ce que l'on utilise, comme colorant rouge, un colorant de formule (6) ou (7) et, comme colorant jaune ou orange, un colorant de formule (9) ou (11).
- Procédé conforme à une des revendications 1 à 10, caractérisé en ce que l'on teint ou imprime de la laine ou un matériau fibreux en polyamide synthétique, en particulier un matériau fibreux en polyamide synthétique.
- Mélanges de colorants, caractérisés en ce qu'ils contiennent au moins un colorant anthraquinonique bleu de formule
en conjonction avec au moins un colorant rouge de formule
et au moins un des colorants jaunes ou oranges de formule (3), (4) et (5)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH3719/92 | 1992-12-03 | ||
CH371992 | 1992-12-03 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0601971A1 EP0601971A1 (fr) | 1994-06-15 |
EP0601971B1 true EP0601971B1 (fr) | 1997-03-12 |
Family
ID=4262037
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP93810813A Expired - Lifetime EP0601971B1 (fr) | 1992-12-03 | 1993-11-24 | Procédé de teinture ou d'impression par trichromie |
Country Status (5)
Country | Link |
---|---|
US (1) | US5399183A (fr) |
EP (1) | EP0601971B1 (fr) |
JP (1) | JPH06212576A (fr) |
DE (1) | DE59305745D1 (fr) |
ES (1) | ES2099409T3 (fr) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6443998B1 (en) | 2000-04-14 | 2002-09-03 | Shaw Industries, Inc. | Trichromatic fiber dyeing processes and compositions thereof |
DE102011079114A1 (de) * | 2011-07-14 | 2013-01-17 | Tesa Se | Klebeband mit textilem Träger für die Kabelbandagierung |
CN104447429B (zh) * | 2014-12-25 | 2016-10-05 | 北京泛博化学股份有限公司 | 环保酸性可拔色黄色染料化合物、应用及合成方法 |
CN105753750B (zh) * | 2016-02-16 | 2017-10-24 | 北京泛博清洁技术研究院有限公司 | 裘皮用酸性可拔白黄色染料化合物及其合成与应用方法 |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH570440A5 (fr) * | 1972-08-29 | 1975-12-15 | Ciba Geigy Ag | |
US4447358A (en) * | 1980-10-16 | 1984-05-08 | Ciba-Geigy Corporation | Monoazo compounds |
ATE20099T1 (de) * | 1981-12-29 | 1986-06-15 | Ciba Geigy Ag | Verfahren zum trichromie-faerben oder -bedrucken. |
EP0092512B1 (fr) * | 1982-04-08 | 1986-04-30 | Ciba-Geigy Ag | Procédé de teinture ou d'impression en trois couleurs |
EP0127579B1 (fr) * | 1983-05-25 | 1987-10-07 | Ciba-Geigy Ag | Procédé de teinture ou d'impression en trois couleurs |
US4579561A (en) * | 1984-01-31 | 1986-04-01 | Crompton And Knowles Corporation | Process for trichromatic dyeing polyamide fibers |
US4652269A (en) * | 1984-11-08 | 1987-03-24 | Ciba-Geigy Corporation | Process for the continuous trichromatic dyeing of synthetic polyamide materials: including a blue anthraquinone reactive dye |
US4840643A (en) * | 1988-03-16 | 1989-06-20 | Crompton & Knowles Corporation | Trichromatic combination of dyes for nylon |
DE59004453D1 (de) * | 1989-03-10 | 1994-03-17 | Ciba Geigy | Farbstoffmischung und deren Verwendung. |
GB2236542B (en) * | 1989-10-06 | 1992-04-15 | Sandoz Ltd | Dye mixtures and their use in trichromatic dyeing processes |
ES2079466T3 (es) * | 1989-10-23 | 1996-01-16 | Ciba Geigy Ag | Mezclas de colorantes y su utilizacion. |
-
1993
- 1993-11-24 DE DE59305745T patent/DE59305745D1/de not_active Expired - Fee Related
- 1993-11-24 EP EP93810813A patent/EP0601971B1/fr not_active Expired - Lifetime
- 1993-11-24 US US08/157,852 patent/US5399183A/en not_active Expired - Fee Related
- 1993-11-24 ES ES93810813T patent/ES2099409T3/es not_active Expired - Lifetime
- 1993-11-29 JP JP5297939A patent/JPH06212576A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
JPH06212576A (ja) | 1994-08-02 |
US5399183A (en) | 1995-03-21 |
ES2099409T3 (es) | 1997-05-16 |
EP0601971A1 (fr) | 1994-06-15 |
DE59305745D1 (de) | 1997-04-17 |
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