EP0000331B1 - Verfahren zum Färben linearer Polyamide in der Masse mit Salzen von 1:2 Chromkomplex-monoazofarbstoffen; die damit erzeugten Fasern - Google Patents

Verfahren zum Färben linearer Polyamide in der Masse mit Salzen von 1:2 Chromkomplex-monoazofarbstoffen; die damit erzeugten Fasern Download PDF

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Publication number
EP0000331B1
EP0000331B1 EP78100161A EP78100161A EP0000331B1 EP 0000331 B1 EP0000331 B1 EP 0000331B1 EP 78100161 A EP78100161 A EP 78100161A EP 78100161 A EP78100161 A EP 78100161A EP 0000331 B1 EP0000331 B1 EP 0000331B1
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EP
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Prior art keywords
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alkyl
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Expired
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EP78100161A
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German (de)
English (en)
French (fr)
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EP0000331A1 (de
Inventor
Paul Dr. Lienhard
Abul Dr. Iqbal
Heinz Dr. Peter
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Novartis AG
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Ciba Geigy AG
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
    • C09B69/04—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds
    • C09B69/045—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds of anionic azo dyes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0091—Complexes with metal-heteroatom-bonds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/48—Preparation from other complex metal compounds of azo dyes
    • C09B45/482—Chromium complexes

Definitions

  • the invention relates to dyeing polyamides from the melt with amine salts of 1: 2 metal complexes of monoazo dyes.
  • alkali salt of the 1: 2 metal complexes of monoazo dyes can be used for the mass coloring of synthetic polyamides (see e.g. GB-PS 1 021 737 and 1 264 191 and FR-PS 1 547 128).
  • the colored bodies isolated as alkali salt often stubbornly retain water and absorb water again after storage after sharp drying, which can lead to polymer degradation or corrosion in the spinning system during the spinning process.
  • amine salts to be used according to the invention the amines of which contain more than 12 C atoms, are described in DE-A 743 848. Because of their high solubility in organic solvents, they are used there for coloring paints.
  • FR-A 2032 391 describes the use of the amine salts of the invention for dyeing fabrics made of polyamide fibers, the fabrics being impregnated with a solution of the dye salts in organic solvents and the impregnated fibers being heated to temperatures up to 210 ° C. for a short time.
  • CH-A 524 011 and GB-1 264 191 form the only references in which a dyeing process with fusion of the polyamide particles is described.
  • These patents are mainly concerned with Azofarbstoffalkalisalzen, amine salts are described not explicit, only rhodamine and Diäthylammoniumsalze mentioned, the Rhodaminsalze spun-dyed polyamide fibers with insufficient light fastness he q flat and the Diäthanolammoniumsalze are unsuitable due to excessive Hyproskopizmaschine for the inventive application.
  • DE-A 1 260 652 and 1 226 727 describe the use of azo dye salts of amines, which contain an ether oxygen, for dyeing spinning solutions, including synthetic polyamides.
  • the spinning solutions are shaped into fibers by evaporation of the solvent or by introduction into a precipitation bath. This takes place at temperatures below 100 ° C.
  • Examples of monoamines are methylamine, trimethylamine, ethylamine, diethylamine, triethylamine, propylamine, isopropylamine, 2-isopropoxy-n-propylamine, n-butylamine, isobutylamine, ethyl-n-butylamine, tri- (n-butyi) amine, pentylamines , called n-hexylamine, tri- (2-ethylhexyl) amine, cyclohexylamine, N-methylcyclohexylamine, dicyclohexylamine, n-dodecylamine or stearylamine.
  • diamines such as N, N-dibutylethylenediamine and N-ethylpropylenediamine, but in particular symmetrically constructed alkylenediamines having 2 to 18 carbon atoms, for example ethylene, propylene, tetramethylene, pentamethylene, hexamethylene diamine, 1,12-diaminododecane, 2.11- Diaminododecane, 3,12-diaminotetradecane, 2,11-diamine-2,11-dimethylethyldodecane, 4,13-diamine-3,14-dimethyl-hexadecane, 4,13-diamino-hexadecane, 3,12-diamino-2, 13-dimethyl-tetradecane, 5,14-diaminooctadecane, 4,13-diamino-2,15-dimethyl-hexadecane.
  • alkylenediamines having 2 to
  • Diethylene triamine may be mentioned as an example of a triamine.
  • Suitable linear polyamides for the present process are the polyamides which can be prepared, for example, from s-carpolactam, from ⁇ -aminoundecanoic acid, from hexamethylene diamine and adipic acid or from analogous starting materials.
  • Mixed polyamides, for example composed of E- carpolactam and hexamethylene diamine and adipic acid, are also suitable.
  • the dyes are mixed in solid or liquid form or as a solution with the polyamide by known processes and the mixture obtained is optionally dried.
  • the polyamides to be colored are preferably breaded with the dry dye powder in the form of powders, granules or chips, i.e. mechanically mixed such that the surface of these particles is coated with a layer of the dye.
  • the dye is advantageously in finely divided form.
  • preparations which, in addition to the dye, contain a carrier, preferably a Ca or Mg salt of a higher fatty acid, for example stearic or behenic acid.
  • the polyamide particles containing the dye or the dye preparation are melted and spun by known processes.
  • the dye or dye preparation can also be introduced into the molten polyamide in solid or liquid form and then spun.
  • Uniformly dyed fibers are obtained which are characterized by a high fastness to light, wet, rubbing and heat setting.
  • the dyes are evenly and finely distributed in the colored material. Although their solubilities in organic solvents such as chlorinated hydrocarbons, lower ketones, esters and alcohols are not high, they are often in dissolved form in polyamide.
  • the colored objects expediently contain 0.01 to 3% of dye.
  • the filter cake is washed successively with 600 ml of a 1% formic acid solution and 600 ml of water.
  • the product dried in vacuo (110-115 ° C) weighs 87.8 g. It has a color salt content of 97.1%, contains only 0.25% NaCI and 1% water.
  • reaction mixture is allowed to cool to room temperature and stirred for a further 3 hours at this temperature, the color salt precipitating out in crystalline form. After filtration, washing the suction filter with 50 ml of n-butanol and drying in a vacuum oven at 110-115 ° C, 14.4 g of color salt are obtained.
  • Spinning according to Example 69 in polycaprolactam gives a scarlet-red fiber material which has very good light, wet fastness, heat setting and rub fastness.
  • the precipitated dye is filtered off, washed successively with 150 ml of a 1% formic acid solution and 150 ml of water and finally dried at 110-115 ° C. 17.2 g of color salt are obtained. It contains only 0.057% NaCl and 1.4% H 2 0.
  • the separated product is filtered off, washed with 300 ml of water and dried in a vacuum oven at 110-115 ° C.
  • the butanolic filtrate is shaken twice with 100 ml of water and then completely evaporated in a rotating flask. In this way, a further smaller amount of product is obtained, which is also dried under vacuum at 110-115 ° C.
  • the total yield of color salt is 20.9 g. It contains ⁇ 0.1 table salt.
  • the crystalline color salt is filtered off under a weak vacuum, washed successively with 125 ml of a 1% formic acid solution and 125 ml of water and then dried at 110-115 ° C. under vacuum. 12.9 g of colored salt with a sodium chloride content of 0.039% and a water content of 4.3% are obtained.
  • Example 1 60 g of the dye obtained in Example 1 and 60 g of Mg behenate are worked in a kneader at 120-130 ° C for 1/4 hour. After reaching a homogeneous mixture, the cooled, brittle product is ground. A dye preparation containing 50% color salt is obtained.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Coloring (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Artificial Filaments (AREA)
EP78100161A 1977-06-23 1978-06-15 Verfahren zum Färben linearer Polyamide in der Masse mit Salzen von 1:2 Chromkomplex-monoazofarbstoffen; die damit erzeugten Fasern Expired EP0000331B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH772277 1977-06-23
CH7722/77 1977-06-23

Publications (2)

Publication Number Publication Date
EP0000331A1 EP0000331A1 (de) 1979-01-24
EP0000331B1 true EP0000331B1 (de) 1983-12-28

Family

ID=4329489

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Application Number Title Priority Date Filing Date
EP78100161A Expired EP0000331B1 (de) 1977-06-23 1978-06-15 Verfahren zum Färben linearer Polyamide in der Masse mit Salzen von 1:2 Chromkomplex-monoazofarbstoffen; die damit erzeugten Fasern

Country Status (8)

Country Link
US (1) US4263197A (cs)
EP (1) EP0000331B1 (cs)
JP (1) JPS5413557A (cs)
CA (1) CA1103385A (cs)
CS (1) CS194848B2 (cs)
DE (1) DE2862357D1 (cs)
PL (1) PL106520B1 (cs)
SU (1) SU735173A3 (cs)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3017070A1 (de) * 1980-05-03 1981-11-05 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung salzarmer wasserloeslicher farbstoffe
DE3920029C2 (de) * 1988-06-30 1999-05-20 Clariant Finance Bvi Ltd Farbstoffe zum Färben von Kunststoffen
US5510467A (en) * 1989-01-03 1996-04-23 Sandoz Ltd. Salts of metal-free anionic phenylazopyrazolone dyes having cations containing sterically hindered amine groups
US5942438A (en) 1997-11-07 1999-08-24 Johnson & Johnson Medical, Inc. Chemical indicator for oxidation-type sterilization processes using bleachable dyes
EP1261662B1 (en) * 2000-02-11 2005-06-15 E.I. Dupont De Nemours And Company Thermoplastic resin compositions for laser welding and articles formed therefrom
EP1606438A2 (en) * 2003-03-18 2005-12-21 Ciba SC Holding AG Colored polymeric articles having high melt temperatures
US7294730B2 (en) * 2005-11-30 2007-11-13 Xerox Corporation Colorant compounds
JP2015063631A (ja) * 2013-09-26 2015-04-09 日本化薬株式会社 アゾ化合物
JP7408915B2 (ja) * 2019-01-31 2024-01-09 セイコーエプソン株式会社 インクジェット捺染インク組成物及び記録方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2032391A1 (cs) * 1969-02-25 1970-11-27 Geigy Ag J R

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2814614A (en) * 1953-04-02 1957-11-26 Ciba Ltd New conversion products of azo dyestuffs containing metal compounds in complex union
DE1110786B (de) * 1958-06-12 1961-07-13 Geigy Ag J R Verfahren zur Herstellung von acetonloeslichen Umwandlungsprodukten metallisierter Azofarbstoffe
DE1260652B (de) 1960-08-09 1968-02-08 Basf Ag Verfahren zur Herstellung von Ammoniumsalzen von Metallkomplexfarbstoffen
GB1021737A (en) * 1963-05-08 1966-03-09 Ici Ltd Process for the coloration of polyamides
NL129233C (cs) * 1965-01-15
DE1619357C3 (de) * 1966-12-29 1974-08-08 Basf Ag, 6700 Ludwigshafen Verwendung von hochkonzentrierten, stabilen, mit Wasser in jedem Verhältnis mischbaren, sulfonsäuregruppenfreie 1:2-Chrom- oder Kobaltkomplexe von Azofarbstoffen enthaltenden Stammlösungen zur Bereitung von Färbebädern oder Druckpasten
RO53376A (cs) * 1968-02-02 1973-03-15
DE1814321B2 (de) * 1968-12-12 1971-04-29 Einrichtung fuer die kompensation einer beugungswinkelab haengigen amplitudenaenderung von in einem detektor fuer roentgenquanten erzeugten spannungsimpulsen
FR2212398B1 (cs) * 1972-12-28 1976-06-04 Ugine Kuhlmann
FR2219964B1 (cs) * 1973-03-02 1978-03-03 Ugine Kuhlmann
CH616953A5 (cs) * 1975-08-27 1980-04-30 Sandoz Ag

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2032391A1 (cs) * 1969-02-25 1970-11-27 Geigy Ag J R

Also Published As

Publication number Publication date
DE2862357D1 (en) 1984-02-02
SU735173A3 (ru) 1980-05-15
US4263197A (en) 1981-04-21
PL207862A1 (pl) 1979-02-26
EP0000331A1 (de) 1979-01-24
CA1103385A (en) 1981-06-16
JPS5413557A (en) 1979-02-01
JPS6252079B2 (cs) 1987-11-04
CS194848B2 (en) 1979-12-31
PL106520B1 (pl) 1979-12-31

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