EP0014852B1 - Procédé de teinture en continu ou en semi-continu de mélanges de fibres cellulosiques et de fibres de polyamides synthétiques avec des colorants azoiques produits sur la fibre - Google Patents
Procédé de teinture en continu ou en semi-continu de mélanges de fibres cellulosiques et de fibres de polyamides synthétiques avec des colorants azoiques produits sur la fibre Download PDFInfo
- Publication number
- EP0014852B1 EP0014852B1 EP80100348A EP80100348A EP0014852B1 EP 0014852 B1 EP0014852 B1 EP 0014852B1 EP 80100348 A EP80100348 A EP 80100348A EP 80100348 A EP80100348 A EP 80100348A EP 0014852 B1 EP0014852 B1 EP 0014852B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- continuous
- dyeing
- steamed
- padding
- textile goods
- 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
Links
- 238000000034 method Methods 0.000 title claims abstract description 32
- 239000004952 Polyamide Substances 0.000 title claims abstract description 26
- 229920002647 polyamide Polymers 0.000 title claims abstract description 26
- 239000000203 mixture Substances 0.000 title claims abstract description 24
- 230000008569 process Effects 0.000 title claims abstract description 18
- 229920003043 Cellulose fiber Polymers 0.000 title claims abstract description 14
- 238000010014 continuous dyeing Methods 0.000 title 1
- 238000010015 semi-continuous dyeing Methods 0.000 title 1
- 239000000975 dye Substances 0.000 claims abstract description 37
- 239000000835 fiber Substances 0.000 claims abstract description 32
- 238000004043 dyeing Methods 0.000 claims abstract description 25
- 230000008878 coupling Effects 0.000 claims abstract description 19
- 238000010168 coupling process Methods 0.000 claims abstract description 19
- 238000005859 coupling reaction Methods 0.000 claims abstract description 19
- 239000004753 textile Substances 0.000 claims abstract description 18
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims abstract description 17
- 150000001989 diazonium salts Chemical class 0.000 claims abstract description 16
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims abstract description 13
- -1 diazoamino compound Chemical class 0.000 claims abstract description 13
- 239000004744 fabric Substances 0.000 claims abstract description 12
- 238000001035 drying Methods 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 6
- 238000010306 acid treatment Methods 0.000 claims abstract description 6
- 230000009471 action Effects 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 238000011437 continuous method Methods 0.000 claims abstract description 3
- 230000001476 alcoholic effect Effects 0.000 claims abstract 2
- 238000009980 pad dyeing Methods 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- 239000000243 solution Substances 0.000 description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- 229920000742 Cotton Polymers 0.000 description 14
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 9
- GXJQMKFJQFGQKV-KHPPLWFESA-N 2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS(O)(=O)=O GXJQMKFJQFGQKV-KHPPLWFESA-N 0.000 description 8
- JACPTQMMZGZAOL-KHPPLWFESA-N 2-[methyl-[(z)-octadec-9-enyl]amino]ethanesulfonic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCN(C)CCS(O)(=O)=O JACPTQMMZGZAOL-KHPPLWFESA-N 0.000 description 8
- 238000010025 steaming Methods 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000000987 azo dye Substances 0.000 description 6
- 239000012954 diazonium Substances 0.000 description 6
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
- KHJWSKNOMFJTDN-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetic acid;sodium Chemical compound [Na].OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KHJWSKNOMFJTDN-UHFFFAOYSA-N 0.000 description 5
- 239000003352 sequestering agent Substances 0.000 description 5
- 235000002639 sodium chloride Nutrition 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- XDWATWCCUTYUDE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-hydroxynaphthalene-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=O)C1=CC2=CC=CC=C2C=C1O XDWATWCCUTYUDE-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000002657 fibrous material Substances 0.000 description 3
- 150000004780 naphthols Chemical class 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 2
- AQYMRQUYPFCXDM-UHFFFAOYSA-N 3-hydroxy-n-(2-methoxyphenyl)naphthalene-2-carboxamide Chemical compound COC1=CC=CC=C1NC(=O)C1=CC2=CC=CC=C2C=C1O AQYMRQUYPFCXDM-UHFFFAOYSA-N 0.000 description 2
- FBLAHUMENIHUGG-UHFFFAOYSA-N 3-hydroxy-n-(2-methylphenyl)naphthalene-2-carboxamide Chemical compound CC1=CC=CC=C1NC(=O)C1=CC2=CC=CC=C2C=C1O FBLAHUMENIHUGG-UHFFFAOYSA-N 0.000 description 2
- JFGQHAHJWJBOPD-UHFFFAOYSA-N 3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1 JFGQHAHJWJBOPD-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 241001584775 Tunga penetrans Species 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920006306 polyurethane fiber Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- ZUVPLKVDZNDZCM-UHFFFAOYSA-N 3-chloro-2-methylaniline Chemical compound CC1=C(N)C=CC=C1Cl ZUVPLKVDZNDZCM-UHFFFAOYSA-N 0.000 description 1
- RLNNKLNZXOUFDY-UHFFFAOYSA-M 3-chlorobenzenediazonium;chloride Chemical compound [Cl-].ClC1=CC=CC([N+]#N)=C1 RLNNKLNZXOUFDY-UHFFFAOYSA-M 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 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
- D06P3/82—Textiles which contain different kinds of fibres
- D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
- D06P3/8219—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and amide groups
-
- 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
- D06P1/02—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 azo dyes
- D06P1/12—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 azo dyes prepared in situ
- D06P1/127—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 azo dyes prepared in situ using a stabilised diazo component, e.g. diazoamino, anti-diazotate or nitrosamine R-N=N-OK, diazosulfonate, hydrazinesulfonate, R-N=N-N-CN
Definitions
- the present invention relates to a process for the continuous or semi-continuous, single-bath, uniform tone-on-tone dyeing of textile fabrics or knitted fabrics from mixtures of cellulose fibers and synthetic polyamide fibers by a block dyeing technique with a coupling component and a diazo component in the form of a stabilized diazonium compound Insoluble azo dyes produced on the fiber by the dye components being applied together under alkaline conditions and the dye development being brought about by the action of acid.
- a one-bath process for the production of water-insoluble azo dyes on cellulose fibers occupies a special position in which, in addition to a coupling component (hereinafter referred to as «naphthol»), one in the form of a one stabilized by reaction of the diazotized amine with cyanamide and therefore not easily coupling-capable diazonium compound (hereinafter referred to briefly as “diazo salt”) is padded onto the goods and the coupling-capable diazonium compound is subsequently released again by an acid treatment and brought to coupling with the “naphthol.
- diazo salt not easily coupling-capable diazonium compound
- the dyeing of synthetic polyamide fibers with developing dyes is also known, but has never been of great importance because of the process steps to be used, which include a change of liquor.
- the polyamide fiber material is dyed with a liquor composed of an alkaline naphthol and a non-coupling-capable, water-insoluble diazonium compound stabilized by triazine formation in the form of a fine dispersion using a pull-out process, and then, after the stabilizing residue has been split off, the dye coupling of the two components is carried out brought about treatment in a hot developing bath containing sulfuric acid.
- stretch cords - a textile article made of polyurethane threads spun with synthetic polyamide threads and cotton - in practice referred to as stretch cords - has become increasingly important. Because of the tightness of the polyamide encapsulation, the polyurethane fiber itself does not need to be dyed, provided the polyamide threads can be dyed tone-on-tone with the cotton pile.
- a water-soluble diazoamino compound composed of a diazotized, aromatic or heterocyclic amine and cyanamide is used as the diazo component in that both dye components are dissolved in an aqueous, alcohol-containing liquor at temperatures of 60 ° to 70 ° C. on the textile material , and that one dampens this primer immediately after padding and before the acid treatment necessary for the release of the diazonium compound and coupling without intermediate drying.
- the fiber material has previously been padded close to the cooking temperature in order to reduce the substantivity of the «naphthols and to obtain the same colors. If you use this temperature for dyeing polyamide-cellulose fiber mixtures, you get false stains because it is not possible to apply the dye components evenly to both types of fiber.
- the coupling component and the diazo salt are dissolved in accordance with the dissolving instructions of the manufacturers and added to the padding liquor which is 60 ° to 70 ° C. and contains the usual chemicals.
- the fiber mixtures themselves are padded at 60 ° to 70 ° C on one of the usual padding pad machines with 60 to 100% liquor absorption (based on the weight of the dry goods).
- the primed textile is steamed without preliminary drying. Steaming is carried out at temperatures of 101 ° to 107 ° C., preferably 103 ° to 105 ° C., and at steaming times of 30 seconds to 5 minutes, preferably shorter, namely 30 seconds to 2 minutes. If an HT damper is present, the goods can also be steamed at 120 ° to 135 ° C. for 30 to 120 seconds without the result of the tone-on-tone coloring being impaired.
- the acid treatment of the fiber material treated with the dye components is carried out in a fresh bath in order to bring about the coupling ability of the «diazo salt and dye coupling according to one of the three usual methods: continuously by padding with the acid or through an acid passage in a wide washing machine, or semi-continuously in the jigger.
- the dye components for the new process are the Color Index, 3rd edition 1971, as Azoic Coupling Components ("Naphthole •) and the diazoamino compounds obtained by reaction with cyanamide of the diazotized chemical compounds listed as Azoic Diazo Components (" Diazo salts ”) in question.
- the low to medium substantive products are preferably used for the block process.
- diazo salts which are preferably suitable according to the invention, the derivatives of:
- the new process can be used for any type of blended fabrics and blended fabrics made of cellulose and polyamide fibers in any mixing ratio.
- the main thing is to dye stretch cord fabrics and knitted fabrics for outerwear, such as nickies and training suits.
- the percent (%) designation used in the following exemplary embodiments of information about the composition of the fiber mixture or for the strength of the chemicals relates to “percent by weight”.
- Solution 2 is then stirred into the bath batch and this is made up to a volume of 200 l with water at 70 ° C.
- the padding liquor thus obtained is padded at 70 ° C and with a 70% liquor absorption (based on the weight of the dry goods) and steamed immediately after padding, without intermediate drying, for 2 minutes at 105 ° C.
- a textile material dyed evenly brick red in the proportions of polyamide fiber and cotton is obtained.
- the stretch cord is bent along a rib, the polyamide fiber that appears shows the same color and depth as the cotton pile.
- Solution 2 is then stirred into the bath batch and this is filled up with water at 60 ° C. to a volume of 3001.
- the cord is padded at 60 ° C and with 70% liquor absorption (from the weight of the goods).
- the damp tissue is steamed for 4 minutes at 102 ° C.
- the cord is padded with 100% liquor absorption of the product weight, then subjected to an air passage of 30 seconds at room temperature and the dyeing thus obtained is rinsed in the 1st case of a board washing machine with water at 70 ° C. Finally, the colored goods are soaped in the remaining boxes of the wide-width washing machine in accordance with Example 1.
- a full, clear orange dyeing of the cord is obtained with very good tone-on-tone dyeing of polyamide and cotton fibers.
- the dye material is then dried at 110 ° C for better dye utilization.
- the steaming according to the invention is omitted before drying, a significantly lighter coloration is obtained on the polyamide fiber portion, which is not useful in practice.
- the fabric is padded at 60 ° C and 70% liquor absorption (based on the weight of the goods) and then steamed at 125 ° C for 30 seconds without drying.
- a uniform scarlet dyeing with good tone-on-tone dyeing of cotton pile and the polyamide wound around the polyurethane threads are obtained.
- the stretch properties of the goods are not affected in any way.
- Dye 270 kg of a mixture of polyamide fiber and cotton in a ratio of 20:80. With a planned fleet intake of 70%, 190 I block fleet + 30 I chassis filling 220 I fleet are required.
- the textile goods After padding the textile goods at 70 ° C and 70% liquor absorption (by the weight of the goods), they are steamed for 3 minutes at 102 ° C while wet and then the dye is developed with the same additives as in Example 1 and the dyed goods are post-treated.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT80100348T ATE930T1 (de) | 1979-01-26 | 1980-01-23 | Verfahren zum kontinuierlichen oder halbkontinuierlichen faerben von mischungen aus cellulosefasern und synthetischen polyamidfasern mit azo-entwicklungsfarbstoffen. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2902977A DE2902977C2 (de) | 1979-01-26 | 1979-01-26 | Verfahren zum kontinuierlichen oder halbkontinuierlichen Färben von Mischungen aus Cellulosefasern und synthetischen Polyamidfasern mit Azo-Entwicklungsfarbstoffen |
DE2902977 | 1979-01-26 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0014852A1 EP0014852A1 (fr) | 1980-09-03 |
EP0014852B1 true EP0014852B1 (fr) | 1982-04-28 |
Family
ID=6061443
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP80100348A Expired EP0014852B1 (fr) | 1979-01-26 | 1980-01-23 | Procédé de teinture en continu ou en semi-continu de mélanges de fibres cellulosiques et de fibres de polyamides synthétiques avec des colorants azoiques produits sur la fibre |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP0014852B1 (fr) |
AT (1) | ATE930T1 (fr) |
DE (2) | DE2902977C2 (fr) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3514111A1 (de) * | 1985-04-19 | 1986-10-23 | Hoechst Ag, 6230 Frankfurt | Verfahren zum endengleichen faerben von cellulosefasermaterialien mit azo-entwicklungsfarbstoffen |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1021901A (fr) * | 1950-07-11 | 1953-02-25 | Francolor Sa | Procédé de formation de colorants azoïques insolubles sur matières textiles, à bse de polymères synthétiques à poids moléculaire élevé |
DE1262957C2 (de) * | 1963-10-19 | 1968-10-03 | Hoechst Ag | Verfahren zur Erzeugung von wasserunloeslichen Azofarbstoffen auf Textilmaterial aus Cellulose- oder Eiweissfasern |
US3617180A (en) * | 1968-08-19 | 1971-11-02 | Gaf Corp | Azoic dye composition containing oxygen-containing primary amines and process of using same |
CH592199B5 (fr) * | 1975-02-21 | 1977-10-14 | Ciba Geigy Ag | |
DE2606905A1 (de) * | 1976-02-20 | 1977-08-25 | Hoechst Ag | Verfahren zum klotz-faerben oder bedrucken von materialien aus synthesefasern und deren mischungen mit cellulosefasern |
-
1979
- 1979-01-26 DE DE2902977A patent/DE2902977C2/de not_active Expired
-
1980
- 1980-01-23 AT AT80100348T patent/ATE930T1/de not_active IP Right Cessation
- 1980-01-23 EP EP80100348A patent/EP0014852B1/fr not_active Expired
- 1980-01-23 DE DE8080100348T patent/DE3060310D1/de not_active Expired
Also Published As
Publication number | Publication date |
---|---|
DE2902977C2 (de) | 1980-12-18 |
ATE930T1 (de) | 1982-05-15 |
DE2902977B1 (de) | 1980-04-24 |
DE3060310D1 (en) | 1982-06-09 |
EP0014852A1 (fr) | 1980-09-03 |
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