EP0000331B1 - Procédé de teinture de polyamides linéaires dans la masse au moyen de sels de colorants monoazoique chromifères 1:2; les fibres ainsi obtenues - Google Patents

Procédé de teinture de polyamides linéaires dans la masse au moyen de sels de colorants monoazoique chromifères 1:2; les fibres ainsi obtenues 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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EP0000331A1 (fr
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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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    • 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)

Claims (6)

1. Procédé de teinture de polyamides linéaires avec des sels de colorants monoazoïques chromifères 1:2, par mélange des particules de polyamides avec le colorant, sans eau, élimination du solvant éventuellement présent, chauffage des particules portant le colorant pour les fondre et transformation de la masse fondue en fibres, procédé caractérisé en ce qu'on utilise comme colorants des sels de formule ci-dessous:
Figure imgb0026
dans laquelle:
R1 désigne un alkyle ou un alkylène en C, à C18 ou bien un cycloalkyle ou un cycloalkylène en C5 ou C6,
R3 un atome d'hydrogène, un alkyle ou un alkylène en C1 à C18 ou un cycloalkyle en C5 ou C6,
R2, R4, R5, R6 et R7 représentent des atomes d'hydrogène, des alkyles en C1 à C18 ou des cycloalkyles en C5 ou C6,
p et q sont chacun le nombre zéro ou un, q étant nul si R3 est un atome d'hydrogène, et t = p + q + 1,
m et t sont chacun un nombre de un à trois,
m r = m-1 et n = ―, t
X représente un groupe ―COO⊖ ou ―SO3 ⊖ lié à la composante colorant mais non au chrome,
X1 et X2 désignent des atomes d'hydrogène, des groupes alkyles, alcoxy ou alkylsulfonyles en C, à C6, des groupes alcanoylamino en C2 à C6 ou des groupes SO2NRR',
R étant un atome d'hydrogène, un alkyle en C1 à C6, un hydroxyalkyle en C2 à C6, un alcoxyalkyle en C3 à C8 ou un phényle éventuellement subsituée par des atomes d'halogènes ou par des alkyles en C1 à C4, et R' étant un atome d'hydrogène, un alkyle en C, à C6 ou un hydroxyalkyle en C2 à C6,
Y1 et Y2 désignant l'hydrogène ou des atomes d'halogènes ou des alkyles en C1 à C6, ou bien
X1 et Y1 ou
X2 et Y2 forment ensemble un cycle benzénique condensé,
Z et Z1 sont des atomes d'oxygène ou des groupes -COO-, et les radicaux
Figure imgb0027
représentent des groupes
Figure imgb0028
dans lesquels
Q est un groupe méthyle ou carbamoyle ou un alcoxycarbonyle en C2 à C6,
W1 un atome d'hydrogène ou d'halogène ou un groupe méthyle ou sulfamoyle,
W2 un atome d'hydrogène ou d'halogène, et
W3 un atome d'hydrogène ou un groupe alcanoylamino en C2 à Cs.
2. Procédé selon la revendication 1 caractérisé en ce que l'on utilise des complexes de chrome symétriques dans lesquels:
X1 = X2, Y, = Y2 et Z = Z1, et les radicaux
Figure imgb0029
sont chacun un radical
Figure imgb0030
les symboles Q, W1 et W2 ayant les significations données à la revendication 1.
3. Procédé selon la revendication 1 ou 2, caractérisé en ce que l'on utilise des sels d'amines de complexes de chrome sans groupe sulfonique ni groupe carboxylique libre.
4. Procédé selon la revendication 1 caractérisé en ce que l'on utilise des sels comportant un cation de formule:
Figure imgb0031
dans laquelle
R8 désigne un atome d'hydrogène ou un alkyle en C1 à C4,
R9 est identique à R8 mais peut être aussi un groupe cyclopentyle, cyclohexyle ou phényle, et
R10 est un alkylène à chaîne droite ou ramifiée en C1 à C18.
5. Procédé selon la revendication 4 caractérisé en ce que l'on utilise des sels d'alkylène-diamines en C2 à C12.
6. Les polyamides linéaires contenant dans la mass un colorant selon l'un quelconque des revendications précédentes.
EP78100161A 1977-06-23 1978-06-15 Procédé de teinture de polyamides linéaires dans la masse au moyen de sels de colorants monoazoique chromifères 1:2; les fibres ainsi obtenues Expired EP0000331B1 (fr)

Applications Claiming Priority (2)

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

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EP0000331B1 true EP0000331B1 (fr) 1983-12-28

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

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
US20020156161A1 (en) * 2000-02-11 2002-10-24 Reiko Koshida Thermoplastic resin compositions for laser welding and articles formed therefrom
JP4563998B2 (ja) * 2003-03-18 2010-10-20 チバ ホールディング インコーポレーテッド 高い溶融温度を有する着色される高分子物品類
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 (fr) * 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 (fr) * 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 (fr) * 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 (fr) * 1972-12-28 1976-06-04 Ugine Kuhlmann
FR2219964B1 (fr) * 1973-03-02 1978-03-03 Ugine Kuhlmann
CH616953A5 (fr) * 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 (fr) * 1969-02-25 1970-11-27 Geigy Ag J R

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

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