AU605705B2 - Mixture of assistants and its use in the dyeing of polyester fibre materials - Google Patents
Mixture of assistants and its use in the dyeing of polyester fibre materials Download PDFInfo
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- AU605705B2 AU605705B2 AU50025/90A AU5002590A AU605705B2 AU 605705 B2 AU605705 B2 AU 605705B2 AU 50025/90 A AU50025/90 A AU 50025/90A AU 5002590 A AU5002590 A AU 5002590A AU 605705 B2 AU605705 B2 AU 605705B2
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- 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
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
-
- 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
- D06P1/613—Polyethers without nitrogen
- D06P1/6131—Addition products of hydroxyl groups-containing compounds with oxiranes
- D06P1/6135—Addition products of hydroxyl groups-containing compounds with oxiranes from aromatic alcohols or from phenols, naphthols
-
- 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
- D06P1/64—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 low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/649—Compounds containing carbonamide, thiocarbonamide or guanyl groups
- D06P1/6495—Compounds containing carbonamide -RCON= (R=H or hydrocarbons)
- D06P1/6498—Compounds containing -CONCO-, e.g. phthalimides, hydantoine; Compounds containing RCONHSO2R (R=H or hydrocarbon)
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- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
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Description
t' I- FORM COMMONWEALTH OF AUSTRALIA PATENTS ACT 1952 COMPLETE SPECIFICATION
(ORIGINAL)
FOR OFFICE USE: Class Int Class *0 «t t t ,e e t 1 t 0 I 0 t
I.
a 000 ae
S*
Oe B 0000 D 00ft 0 <>000 0 0 0 00* o a 00 0 0 0 0 0 00* Complete Specification Lodged: Accepted: Published: Priority: Related Art: This document contains the j amendments made under Section 49 and is correct for priinting.
Name and Address of Applicant: Address for Service: Ciba-Geigy AG Klybeckstrasse 141 4002 Basle
SWITZERLAND
Spruson Ferguson, Patent Attorneys Level 33 St Martins Tower, 31 Market Street Sydney, New South Wales, 2000, Australia Complete Specification for the invention entitled: Mixture of Assistants and its Use in the Dyeing of Polyester Fibre Materials The following statement is a full description of this invention, including the best method of performing it known to me/us 5845/4 s -1A The present invention relates to a novel mixture of assistants and to its use in the dyeing of polyester fibre materials.
The mixture of assistants comprises at least one dicarboxyimidoester of the formula
CO
N-(CH2 COOR co in which N represents a divalent aliphatic radical having at least 2 carbon atoms or a divalent cycloaliphatic or aromatic radical, R is an aliphatic, o, araliphatic or cycloaliphatic radical having not more than 24 carbon atoms and preferably not more than 12 carbon atoms, and n is 2 to one acid ester, or salts thereof, of an alkylene oxide adduct of the formula o (v) *t m 0---alkylene--O0---X S& n (Y)m in which V is hydrogen or methyl, X is the acid radical of an inorganic acid containing oxygen, for example sulfuric acid or phosphoric acid, or is the radical of an organic acid and Y is an a-methylaralkyl radical, "alkylene" is the ethylene radical or the propylene radical and m is 1 to 3, m I is 1 or 2 and n 1 is 4 to 50, and a nonionic surfactant which preferably contains polyethylene glycol ether groups.
The mixture of assistants according to the invention advantageously contains 20 to 70 per cent by weight of the component 15 to 40 per cent by weight of the component (B) 1 -2- Sand 15 to 40 per cent by weight of the component i i Components and can be present as individual compounds or in the form of a mixture of two or more compounds with one another.
It is preferable to employ mixtures of the components and together.
In the formula W is -fr example a divalent, aliphatic, cycloaliphatic or aromatic radical which is attached to the carboxyl groups of the imide grouping.
When W is a divalent, aliphatic radical, it is advantageously a linear or branched hydrocarbon radical, which is unsubstituted or substituted by halogen, of a saturated or ethylenically unsaturated dicarboxylic acid having 4 to 10 carbon atoms. Examples of suitable aliphatic, saturated dicarboxylic acids of this type are succinic acid and glutaric S'acid. Ethylenically unsaturated dicarboxylic acids are preferably maleic acid, dimethylmaleic acid, dichloromaleic acid, citraconic acid, glutaconic acid or itaconic acid.
When W is a divalent, cycloaliphatic radical, it is, in particular, the radical of a tetrahydrophthalic or hexahydrophthalic acid.
W is preferably the divalent radical of an aromatic dicarboxylic acid, for example a i naphthalenedicarboxylic acid or phthalic acid.
W is preferably a phenylene radical which can be substituted by halogen, for example chlorine or bromine, C1-C 4 alkyl, such as methyl or tert-butyl, or C 1
-C
4 alkoxy such as methoxy. In particular, W is an unsubstituted phenylene radical.
An aliphatic radical R can be saturated or unsaturated and linear or branched. R is advantageously an alkyl radical having 1 to 24, preferably 1 to 12, carbon atoms.
Examples of such alkyl radicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, pentyl, n-hexyl, 2-ethylhexyl, 1,1,3,3-tetramethylbutyl, n-octyl, n-dodecyl, myristyl, octadecyl, arachidyl or behenyl. A cycloaliphatic radical R is, in particular, a cyclopentyl radical or, especially, a cyclohexyl radical. The benzyl radical in particular is suitable for R as an araliphatic radical, n is preferably Dicarboxyimidoesters of the formula of industrial importance have the formula
I~
-3-
CO
Wi N (CH 2 5
COOR
1
CO
in which W 1 is alkylene or alkenylene having 2 to 4 carbon atoms, cyclohexylene or phenylene which is unsubstituted or substituted by halogen, for example chlorine or bromine, methyl or methoxy and R 1 is alkyl having 1 to 12 carbon atoms, preferably 3 to 8 carbon atoms, cyclohexyl or benzyl.
The following are typical representatives of the dicarboxyimidoesters used in accordance with the invention: methyl phthalimidohexanoate, ethyl phthalimidohexanoate, propyl phthalimidohexanoate, n-butyl phthalimidohexanoate, 2-ethylhexyl phthalimidohexanoate, n-butyl hexahydrophthalimidohexanoate, 2-ethylhexyl hexahydrophthalimidohexanoate, n-butyl tetrahydrophthalimidohexanoate, n-butyl tetrachlorophthalimidohexanoate, 2-ethylhexyl tetrachlorophthalimidohexanoate, n-butyl succinimidohexanoate and S2-ethylhexyl tetrahydrophthalimidohexanoate.
Amongst these representatives the said C 1
-C
8 alkyl phthalimidohexanoates and particularly
C
3 -Cgalkyl phthalimidohexanoates, such as, in particular, 2-ethylhexyl S phthalimidohexanoate, are particularly preferred.
The preparation of the compounds of the formulae and is effected in a manner known per se. The preparation can preferably be effected by reacting a dicarboxylic anhydride of the formula
CO
O
I (la) co with a compound of the formula (CH2) in the presence of an alcohol of the
NH
formula (Ic) R-OH.
Compounds of the formulae and and their preparation are described, for example, in US Patent Specification 3,210,313.
-4- Individual examples of starting materials of the formula (la) are maleic anhydride, dimethylmaleic anhydride, dichloromaleic anhydride, succinic anhydride, dimethylsuccinic anhydride, citraconic anhydride, glutaric anhydride, itaconic anhydride, glutaconic anhydride, phthalic anhydride, tetrachlorophthalic anhydride, tetrahydrophthalic anhydride or hexahydrophthalic anhydride.
Individual examples of starting materials of the formula (ib) are a-pyrrolidone, a-piperidone or, preferably, e-caprolactam.
Individual examples of alcohols of the formula (Ic) are methanol, ethanol, n-butanol, S, sec-butanol, tert-butanol, amyl alcohol, hexanols, 2-ethylhexanol, octyl alcohols, decyl r, alcohols, dodecyl alcohols, cyclohexanol or benzyl alcohol. These alcohols can be used on their own or as mixtures.
t t The substituent Y in formula advantageously contains 8 to 12 carbon atoms and is, in e t particular, a-methylbenzyl, a,a-dimethylbenzyl, a-tolylethyl or a-xylylethyl.
a-Methylbenzyl is particularly preferred.
(Alkylene-O)n- chains are preferably of the ethylene glycol, propylene/ethylene glycol or ethylene/propylene glycol type; the first-mentioned is particularly preferred.
nj is preferably 4 to The acid radical X is derived, for example, from low-molecular dicarboxylic acids, for example maleic acid, succinic acid or sulfosuccinic acid, and is attached to the S, I alkyleneoxy moiety of the molecule via an ester bridge. In particular, however, X is derived from inorganic, polybasic acids, such as sulfuric acid or orthophosphoric acid.
The acid radical X can be present as the free acid or in a salt form, for example, as an alkali metal, ammonium or amine salt. Examples of such salts are lithium, sodium, potassium, ammonium, trimethylamine, diethylamine, ethanolamine, diethanolamine or triethanolamine salts. Alkali metal salts or triethanolamine salts are preferred. The monoethanolamine or diethanolamine salts can be further etherified with 1 to 4 oxethylene units.
Preferred acid esters of the component have the formula
CH
2
CH
2
X
1 Y) m (Yl)m in which Y 1 is a-methylbenzyl, a,a-dimethylbenzyl or a-tolylethyl, X 1 is an acid radical derived from sulfuric acid or, preferably, o-phosphoric acid and m is 1 to 3 and n 2 is 4 to These acid esters are preferably in the form of sodium, potassium, ammonium, S, diethylamine, triethylamine, diethanolamine or triethanolamine salts.
The acid esters of the formula or which are suitable as component are prepared by adding an alkylene oxide (ethylene oxide or propylene oxide) onto a phenol compound substituted in the manner defined, and converting the adduct by means of a polybasic oxygen acid or a functional derivative of this acid, for example acid anhydrides, acid halides, acid esters or acid amides, into the acid esters and, if appropriate, converting the acid ester obtained into the abovementioned salts. Examples of these functional derivatives which may be mentioned are phosphorus pentoxide, phosphorus oxytrichloride, chlorosulfonic acid or sulfamic acid. Both the alkylene oxide addition and the esterification can be carried out by known methods.
Components which are very suitable are acid esters, or salts thereof, of a polyadduct of 4 to 40 moles of ethylene oxide onto 1 mole of a phenol containing at least one a-tolylethyl group, an a-methylbenzyl group or an a,a-dimethylbenzyl group, for example a-tolylethylphenol, a-methylbenzylphenol, bis-(a-methylbenzyl)-phenol or tris-a-(methylbenzyl)-phenol, it being possible to use these acid esters on their own or as a mixture.
Esters of particular interest are acid phosphoric acid esters or sulfuric acid esters of adducts of 8 to 30 moles of ethylene oxide onto 1 mole of compounds prepared by adding 1 to 3 moles of styrenes onto 1 mole of phenols, the phosphoric acid esters preferably being present as mixtures of the corresponding salts of a monoester and a diester.
The preparation of the styrene adducts is effected in a known manner, preferably in the presence of catalysts, such as sulfuric acid, p-toluenesulfonic acid or zinc chloride.
J
I 2 -6- Suitable styrenes are preferably styrene, a-methylstyrene or vinyltoluene (4-methylstyrene). Examples of the phenols are phenol, cresols or xylenols.
Acid phosphoric acid esters (monoesters and diesters) or sulfuric acid esters, or salts thereof, of alkoxylation products of the formula CH2- CH2- H CH3 Q m i in which m is 1 to 3 and n 3 is 12 to 30 are very particularly preferred.
I t T 4 The following may be mentioned individually as examples of alkoxylation products of the 2a formulae and An alkoxylation product having 18 ethylene oxide units of the adduct of 2 moles of styrene onto 1 mole of phenol, an alkoxylation product having 18 ethylene oxide units of the adduct of 3 moles of styrene onto 1 mole of phenol, an alkoxylation product having 27 ethylene oxide units of the adduct of 2 moles of 4-methylstyrene onto 1 mole of phenol, an alkoxylation product having 17 ethylene oxide units of the adduct of 3 moles of 4-methylstyrene onto 1 mole of phenol, an alkoxylation product having 18 ethylene oxide units of the mixture of an adduct of 2 moles of styrene onto 1 mole of phenol and an adduct of 3 moles of styrene onto 1 mole of phenol, and an alkoxylation product having 13 ethylene oxide units of the mixture of an adduct of 2 moles of styrene onto 1 mole of phenol and an adduct of 3 moles of styrene onto 1 mole of phenol.
The nonionic surfactant used as component is advantageously an alkylene oxide adduct of 2 to 100 moles of alkylene oxide, for example ethylene oxide and/or propylene oxide, onto 1 mole of an aliphatic monoalcohol having at least 4 carbon atoms, of a trihydric to hexahydric aliphatic alcohol preferably having 3 to 6 carbon atoms, of a
I"
-7phenol which is unsubstituted or substituted by C 4
-C
12 alkyl, phenyl, a-tolylethyl, benzyl, a-methylbenzyl or a,a-dimethylbenzyl, or of a fatty acid having 8 to 22 carbon atoms.
The following examples of nonionic surfactants may be mentioned: Adducts of, preferably, 2 to 80 moles of alkylene oxide, in particular ethylene oxide, it being possible for individual ethylene oxide units to be replaced by substituted epoxides, such as styrene oxide and/or propylene oxide, onto higher unsaturated or saturated monoalcohols, fatty acids, fatty amines or fatty amides having in each case 8 to 22 carbon atoms, or onto benzyl alcohols, phenylphenols, benzylphenols, p-phenethylphenols, a-methylbenzylphenols, a,a-dimethylbenzylphenols, a-tolylethylphenols or alkylphenols in which the alkyl radicals contain at least 4 carbon atoms; alkylene oxide, in particular ethylene oxide and/or propylene oxide, condensation products 'i (block polymers); i ethylene oxide/propylene oxide adducts onto fatty amines or diamines, in particular ethylenediamine; reaction products formed from a fatty acid containing 8 to 22 carbon atoms and a primary or secondary amine containing at least one hydroxy-lower alkyl or lower alkoxy-lower alkyl group, or alkylene oxide adducts of these reaction products containing hydroxyalkyl groups, the reaction being carried out in such a way that the molecular ratio between hydroxyalkylamine and fatty acid can be 1:1 and greater than 1, for example 1:1 to 2:1, and sorbitan esters, preferably having C 6
-C
24 fatty acid ester groups, or polyethoxylated sorbitan esters, for example polyoxethylene-sorbitan monolaurate or monooleate or monostearate having in each case 4 to 20 ethylene oxide units or polyoxethylene-sorbitan trioleate having 4 to 20 ethylene oxide units.
Fatty alcohol polyglycol mixed ethers, in particular adducts of 3 to 30 moles of ethylene oxide and 3 to 30 moles of propylene oxide onto aliphatic monoalcohols having 8 to 22 carbon atoms, preferably alkanols having 8 to 16 carbon atoms.
Of these, the abovementioned alkoxylation products of the formula derived from -8styrene adducts are particularly preferred as nonionic surfactants.
Other nonionic surfactants which are particularly preferred can be represented by the formula R'-O-(alkylcnc-0- CO-T n1 or by the formula O-f alkylene- CH20-- CH2CH20-- CO- T t z (Y)m Sin which R' is an alkyl or alkenyl radical having in each case 8 to 24 carbon atoms or a Sradical of the formula 6(a) (Y)m T is an aliphatic radical having 8 to 30 carbon atoms and z is 1 to 25 and Y, m, nj and "alkylene" are as defined above.
The compounds of the formula can be prepared by reacting the adduct of the formula R'-O-(alkylene-O)n -H with a fatty acid T-COOH or by reacting an alcoholic or phenolic compound R'-OH with a fatty acid ester of the formula T-CO-(alkylene-O)n -H.
The compounds of the formula are reaction products formed from adducts of the formula alkylene- 0--n H,formaldehyde or a formaldehyde donor, for (Y)m example paraformaldehyde, and a fatty acid ester of the formula T-CO-O-(CH 2
CH
2 O)z-H, and some are described in Japanese Preliminary Published Specification JP-A 83,18486.
Compounds which fall under formula and are not mentioned there can be prepared correspondingly, the reaction conditions mentioned in the Japanese Preliminary Published I II -9- Specification resulting in the desired products of the formula Components which are very suitable also have the formula R- O-(CHCHO)-- CH-CH- OH II
I
in which R 1 is alkyl or alkenyl having in each case 8 to 22 carbon atoms, one of Z 1 and Z 2 is phenyl and the other is hydrogen and s is 4 to The compounds of the formula are prepared by adding styrene oxide onto the polyethylene glycol ether of the formula R"-O-(CH 2 The novel preparations of assistants can be prepared merely by stirring together the said components and, if appropriate, together with water, homogeneous clear mixtures being obtained which are distinguished by good stability on transport and Sstorage. The mixtures of assistants according to the invention are, in particular, very stable at elevated temperatures of up to 130°C, when they are employed in dyebaths. They increase the rate of diffusion of the dyes when dyeing polyester fibre materials, preferably linear polyester fibres.
Accordingly, the present invention also relates to a process for dyeing polyester fibre material by means of disperse dyes, which comprises dyeing this material in the presence of the mixture of assistants according to the invention.
The amount in which tie combination of assistants according to the invention is added to Sthe dyebaths rangeAfror0.3 to 6 g, preferably 0.5 to 4 g per litre of dye liquor.
Examples which may be mentioned of polyester fibre material, in particular textile material, which can be dyed in the presence of the novel mixture of assistants are cellulose ester fibres, such as cellulose acetate and triacetate fibres and, in particular, linear polyester fibres. Linear polyester fibres are to be understood here as meaning synthetic fibres which are obtained, for example, by the condensation of terephthalic acid with ethylene glycol or of isophthalic acid or terephthalic acid with 1,4-bis-(hydroxymethyl)-cyclohe.xane, and also copolymers formed from terephthalic and isophthalic acid and ethylene glycol. The linear polyester which has hitherto been f
I
employed almost exclusively in the textile industry consists of terephthalic acid and ethylene glycol.
The fibre materials can also be used in the form of mixed fabrics, with each other or with other fibres, for example mixtures of polyacrylonitrile/polyester, polyamide/polyester, polyester/cotton, polyester/viscose and polyester/wool.
The textile material to be dyed can be in various stages of processing. For example, the following are suitable: loose material, piece goods, such as knitted or woven fabrics, and yarn in package or muff form. The latter can have a package density of 200 to 600 g/cm 3 in particular 400 to 450 g/cm 3
I
The disperse dyes to be used, which are only very slightly soluble in water and are present in the dye liquor for the most part in the form of a fine dispersion, can belong to a very wide range of classes of dye, for example the acridone, azo, anthraquinone, coumarin, methine, perinone, quinophthalone, naphthoquinoneimine, styryl or nitro dyes.
According to the present invention it is also possible to use mixtures of disperse dyes.
Mixtures are used in particular for preparing level mixed shade dyeings including dichromatic and trichromatic dyeing. Trichromatic dyeing is in particular the dyeing with a triple combination of the primary colours yellow (or orange), red and blue.
The amount of dyes to be added to the liquor depends on the tinctorial strength desired; in general, amounts of 0.01 to 10, preferably 0.05 to 5, per cent by weight, relative to the textile material employed, have proved successful.
The assistants to be used according to the present invention can also be used mixed with known carriers based on for example di- or trichlorobenzene, methylbenzene, ethylbenzene, o-phenylphenol, benzylphenol, diphenylether, chlorobiphenyl, methylbiphenyl, cyclohexanone, acetophenone, alkylphenoxyethanol, mono-, di- or trichlorophenoxyethanol or -propanol, pentachlorophenoxyethanol, or based in particular on biphenyl, methyl biphenyl ether, or dibenzyl ether. The carriers are preferably used in amounts of 0.5 g to 2 g/l of liquor or 10 to 60 per cent by weight, based on the assistant formulation.
Depending on the textile material to be treated, the dyebaths can also contain, in addition -11to the dyes and the mixture of assistants according to the invention, oligomeric inhibitors, anti-foaming agents (for example silicone oils or ethylene-bis-fatty acid amides), non-creasing agents and, preferably, dispersants.
The dispersants serve, in particular, to achieve good dispersion of the disperse dyes. The dispersants which are generally customary in dyeing by means of disperse dyes are suitable.
Suitable dispersants are preferably sulfated or phosphated adducts of 15 to 100 moles of ethylene oxide or, preferably, propylene oxide onto polyhydric aliphatic alcohols having 2 to 6 carbon atoms, for example ethylene glycol, glycerol or pentaerythritol or onto amines |i having 2 to 9 carbon atoms and containing at least two amino groups or one amino group S, and one hydroxyl group, and also alkylsulfonates having 10 to 20 carbon atoms in the S alkyl chain, alkylbenzenesulfonates having a linear or branched alkyl chain with 8 to Scarbon atoms in the alkyl chain, for example nonylbenzenesulfonate, dodecylbenzenesulfonate, 1,3,5,7-tetramethyloctylbenzentsulfonate or ^i octadecylbenzenesulfonate, and also alkylnaphthalenesulfonates or sulfosuccinic acid esters, for example sodium dioctylsulfosuccinate or sodium di-2-ethylhexylsulfosuccinate.
Ligninsulfonates, polyphosphates and, preferably, formaldehyde condensation products formed from aromatic sulfonic acids, formaldehyde and phenols which can be monofunctional or bifunctional, for example from cresol, p-naphtholsulfonic acid and formaldehyde, from benzenesulfonic acid, formaldehyde and naphthalenesulfonic acid, from naphthalenesulfonic acid and formaldehyde or from naphthalenesulfonic acid, dihydroxydiphenyl sulfone and formaldehyde, have proved particularly advantageous as anionic dispersing agents. The disodium salt of di-(6-sulfonaphth-2-yl)-methane or tri-(6-sulfonaphth-2-yl)-methane is preferred.
It is also possible to use mixtures of anionic dispersants. Normally, the anionic dispersants are present in the form of their alkali metal salts, ammonium salts or amine salts. These dispersants are preferably used in an amount of 0.5 to 8 g/1 of liquor.
The dyebaths can also contain a water-soluble alkaline earth metal, aluminium or organic ammonium salt of a monobasic or polybasic aliphatic carboxylic acid or of a monobasic or polybasic inorganic acid. By adding these salts it is possible to improve the dispersion stability in the dyebath to a great extent, depending on the type of dye used, in particular i -12in the dyeing of polyester packages of very high pack density. It is thus possible to prevent or greatly reduce dye deposits. These additional salts are water-soluble salts, for example magnesium, calcium, barium, strontium, aluminium or organic ammonium salts of monobasic or polybasic inorganic acids or monobasic or polybasic aliphatic carboxylic acids, such as hydrochloric acid, hydrobromic acid, hydrofluoric acid, nitric acid, sulfuric acid, phosphoric acid or formic acid, acetic acid and thiocyanic acid. Such salts are for example: calcium nitrate, magnesium nitrate, aluminium nitrate, calcium chloride, magnesium chloride, magnesium thiocyanate, calcium thiocyanate or organic ammonium chlorides, bromides or iodides, e.g. methonium salts (alkanebistrimethylammonium salts).
|j Examples of suitable methonium salts are pentamethonium iodide, decamethonium I bromide and in particular hexamethonium chloride.
|i These salts are preferably used in an amount of 0.1 to 3 g per litre of dyeing liquor or 0.2 to 5 per cent by weight, based on the fibre material.
Furthermore, the dyebaths can contain cstomary additives, preferably electrolytes, such as salts, for example sodium sulfate, ammonium sulfate, sodium or ammonium phosphates, sodium or ammonium polyphosphates, ammonium acetate or sodium acetate and/or acids, for example mineral acids, such as sulfuric acid or phosphoric acid, or organic acids, preferably lower aliphatic carboxylic acids, such as formic acid, acetic acid, oxalic acid or citric acid. The acids serve, in particular, to adjust the pH of the liquors used in accordance with the invention, which, as a rule, is 4 to 6.5, preferably 4.5 to 6.
Dyeing is advantageously carried out from an aqueous liquor by the exhaustion process.
The liquor ratio can, accordingly, be selected within a wide range, for example 3:1 to 100:1, preferably 7:1 to 50:1. The temperature at which dyeing is carried out is at least 0 C and, as a rule, is not higher than 140 0 C. It is preferably within the range from 80 to 135 0
C.
Linear polyester fibres and cellulose triacetate fibres are preferably dyed by the so-called high-temperature process in closed, and preferably also pressure-resistant, equipment at temperatures of over 100 0 C, preferably between 110 and 135°C, under pressure. Examples of suitable closed vessels are circulation machines, such as package or beam dyeing machines, winch becks, nozzle or drum dyeing machines, jet or muff dyeing machines, paddle machines or jiggers.
13- Cellulose acetate fibres are preferably dyed at temperatures of 80-85 0
C.
The dyeing process can be carried out in such a way that the material to be dyed is either first treated briefly with the mixture of assistants and is then dyed or, preferably, is treated simultaneously with the mixture of assistants and the dye.
It is preferable to allow the material to be dyed a preliminary run of 5-10 minutes at 40-80'C in the bath which contains the dye, the mixture of assistants and, if appropriate, further additives and whose pH has been adjusted to a value of 4.5 to 6, to raise the temperature in the course of 15 to 30 minutes to 110 to 135 0 C, preferably 125-130 0 C, and to keep the dye liquor for 15 to 30 minutes, preferably 15 to 20 minutes, at this S temperature.
V ft The dyeings are finished by cooling the dye liquor to 60 to 80 0 C, rinsing the dyeings with S water and, if appropriate, reduction clearing them in a customary manner in an alkaline medium under reductive conditions. The dyeings are then rinsed again and dried. Uniform and intense dyeings which are additionally distinguished by good fastness to light and good fastness properties to rubbing are obtained on synthetic fibre material, in particular on linear polyester fibres. The dye liquor remains stable during the dyeing and no deposits are formed in the interior of the dyeing machines.
Compared with known processes which also use disperse dyes that do not migrate or migrate only moderately, the process according to the invention is distinguished by a shortened heating-up phase and by the fact that it is possible to add the dye to the liquor at any desired temperature. In particular, the migration of disperse dyes can be improved by employing the mixture of assistants used in accordance with the invention. By virtue of the improved migration capacity of the dyes, it is possible to level up any possible i unevenness in the absorption phase of the dyes through subsequent migration in the dwell phase at the final temperature. In summary, the dyeing process using the mixture of assistants according to the invention offers the following advantages: unmonitored heating of the liquor to the dyeing temperature without paying special attention to the significant or critical rate of dyeing; shading under customary HT conditions, thanks to the improved migration of the disperse dyes; simple, efficient and reliable performance; -14simple correction of off-shade dyeings, since improved levelling takes place; rapid achievement of level single-shade dyeings, particularly mixed-shade dyeings, including trichromatic dyeings, with good fastness properties, for example fastness to light, rubbing and sublimation, with the avoidance of streakiness and also under difficult circumstances; operation in the main without the addition of conventional carriers, dispersing agents and/or levelling agents; -the achievement of level dyeings with delicate pale and medium shades and, in particular, with deep shades, using dyes fast to sublimation.
In the following examples parts are parts by weight and percentages are percentages by weight.
I t1 S Example 1: 80 parts of a polyester knitted fabric (225 g/m 2 are put into a bath heated to 70 0 C, containing, in 1000 parts of water, 2 g/1 of ammonium sulfate (anhydrous), a dispersed dye mixture of the composition: 0.24 g/1 of a dye of the formula
CH
3
CN
(101) cl N-N--N
NO
2 N
C
2
H
"t t 0.28 g/1 of a dye of the formula t I" Sc C1 (102) NO 2 N= N -NH- CH 2 CH- CH 3
I
OH
NHCOCH
3 and 0.19 g/1 of a dye of the formula i L I .il;i_
NO
2
OCH
3 (103) NO 2 N=N -ONH- CH 2
CH
2
OCH
2
CH
2
CN
Cl NHCOCH 2
CH
3 and 1 g/1 of an assistant formulation consisting of: of 2-ethylhexyl 6-phthalimidohexanoate, of triethanolamine salt of a mixture of the monoester and diester phosphate of an i alkoxylation product having 18 ethylene oxide units of the adduct of 3 moles of t" styrene onto 1 mole of phenol and £I 20 of an alkoxylation product of 18 moles of ethylene oxide with 1 mole of an adduct of S3 moles of styrene onto 1 mole of phenol, the pH of the bath being adjusted to 5 with formic acid.
The liquor is heated to 130°C in the course of 20 minutes, with continuous circulation, and dyeing is carried out at this temperature for 15 minutes. The liquor is then cooled and drained off and the goods are rinsed and dried. A level, brown dyeing is obtained at a high tinctorial yield and with good fastness properties in use. The usual reduction clearing is not necessary.
The 2-ethylhexyl 6-phthalimidohexanoate used is prepared as follows.
148 g of phthalic anhydride, together with 113 g of e-caprolactam, 132 g of 2-ethylhexanol, 1.9 g of p-toluenesulfonic acid and 70 g of 1,3-xylene, are heated to 180 0 C. The water formed is removed by azeotropic distillation. The reaction is complete after 12 hours, 18 ml of water being removed. The solvent is then removed in vacuo. 370 g of the compound of the formula 1 6 -16o S| N-(CH 2 COO- CH 2 CH- (CH 2
CH
3 5c C 2
H
:I II 0 are obtained in the form of a brown oil. Acid number: 6.
Example 2: 100 parts of a knitted fabric composed of texturized polyester fibres are introduced into an incompletely flooded jet dyeing machine containing 1000 parts of water heated to 60 0 C, 2 parts of ammonium sulfate, a finely dispersed dye mixture of the following composition: part of the dye Disperse Yellow 23 C.I. 26,070, S0.14 part of the dye of the formula (104) NO 2 NN N 2H5 and S C 2
H
4
CN
CI
0.23 part of the dye of the formula NH2 O OH (105) OH O NH and and 1 g/l of the assistant formulation according to Example 1, the pH of the liquor being adjusted to 5 with formic acid. The temperature of the liquor is then raised to 130 0 C in the course of 30 minutes and dyeing is carried out at this temperature for 60 minutes. The liquor is then cooled to 90°C and drained off and the goods are rinsed and dried without reduction clearing. A level, brown dyeing with good fastness properties in use is obtained.
7 i 4 i It Vt i4 17- Example 3:100 parts of a knitted fabric composed of texturized polyester fibres are introduced into an incompletely flooded jet dyeing machine containing 1000 parts of water heated to 60 0 C, 2 parts of ammonium sulfate, 2.5 parts of the finely dispersed dye Disperse Yellow 42 C.I. 10,338 and 1.5 parts of the assistant formulation according to Example 1, the pH of the liquor being adjusted to 5 with formic acid.
The temperature of the liquor is raised to 130 0 C in the course of 30 minutes and dyeing is carried out for 30 minutes at this temperature. 0.1 part of the dye of the formula 4 4 t t I i t 4 4 CttI r 4 14 4 4 4 4.44 (106) is then introduced into the liquor for shading, after which the goods are dyed at 130 0 C for a further 30 minutes. The liquor is then cooled and the dyeing is rinsed and finished in the usual manner. A level, brilliant green dyeing with good fastness properties is obtained. As a result of the addition of the assistant formulation mentioned, it is not necessary to cool the liquor before adding the shading dye. This procedure enables time and energy to be saved.
Claims (5)
- 6. j (A T~i t I l 7
- 17. (A in which W represents a divalent aliphatic radical having at least 2 carbon atoms or a divalent cycloaliphatic or aromatic radical, R is an aliphatic, araliphatic or cycloaliphatic radical having not more than 24 carbon atoms and n is 2 to 5, one acid ester or salts thereof of an alkylene oxide adduct of the formula 0--al kyl ene-O- X 1 (Y)M in which V is hydrogen or methyl, X is the acid radical of an inorganic acid containing oxygen, or is the radical of an organic acid, Y is an a-methylaralkyl radical, "alkylene" is the ethylene radical or the propylene radical, m is 1 to 3, m 1 is 1 or 2 and nI is 4 to 50, and a nonionic surfactant. 2. A mixture of assistants according to claim 1, wherein W in formula is unsubstituted phenylene or phenylene which is substituted by halogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxy. 3. A mixture of assistants according to either of claims 1 and 2, wherein R in formula is alkyl having 1 to 12 carbon atoms. 4. A mixture of assistants according to any one of claims 1 to 3, wherein n in formula is I I I I 1 0 034y
- 19- i 5. A mixture of assistants according to claim 1, wherein the dicarboxyimidoester has the I formula co W N- (CH 2 5 COOR 1 CO in which W 1 is alkylene or alkenylene having 2 to 4 carbon atoms, cyclohexylene or phenylene which is unsubstituted or substituted by halogen, methyl or methoxy, and R 1 is I alkyl having 1 to 12 carbon atoms, cyclohexyl or benzyl. i 6. A mixture of assistants according to any one of claims 1 to 5, wherein the component i- S is a C 3 -C 8 alkyl phthalimidohexanoate. i 7. A mixture of assistants according to any one of claims 1 to 6, wherein the component S t is 2-ethylhexyl phthalimidohexanoate. 8. A mixture of assistants according to any one of claims 1 to 7, wherein Y in formula (2) is a-tolylethyl, a-xylylethyl, a,a-dimethylbenzyl or a-methylbenzyl. 9. A mixture of assistants according to any one of claims 1 to 8, wherein nj in formula (2) Sis 4 to K| 10. A mixture of assistants according to any one of claims 1 to 9, wherein the acid radical X in formula is derived from sulfuric acid or orthophosphoric acid. 11. A mixture of assistants according to any one of claims 1 to 10, wherein the component is a compound of the formula O----CH2CH2- X 1 (Y 1 )m in which Y 1 is a-methylbenzyl, a,a-dimethylbenzyl or a-tolylethyl, X 1 is an acid radical derived from sulfuric acid or orthophosphoric acid, and m is 1 to 3 and n 2 is 4 to 12. A mixture of assistants according to claim 1, wherein the component is an acid phosphoric acid ester or sulfuric acid ester or salts thereof of an alkoxylation product of 8 to 30 moles of ethylene oxide added onto 1 mole of a compound which has been prepared by adding 1 to 3 moles of styrene, a-methylstyrene or vinyltoluene onto 1 mole of phenol, cresol or xylenol. 13. A mixture of assistants according to any one of claims 1 to 12, wherein the component is an acid phosphoric acid ester or sulfuric acid ester or salts thereof of an alkoxylation !j product of the formula CH 2 -CH 2 H CH 3 CH in which m is 1 to 3 and n 3 is 12 to 14. A mixture of assistants according to any one of claims 1 to 13, wherein the component is an alkylene oxide adduct of 2 to 100 moles of alkylene oxide onto 1 mole of an aliphatic monoalcohol having at least 4 carbon atoms, of a trihydric to hexahydric aliphatic alcohol having 3 to 6 carbon atoms, of a phenol which is unsubstituted or Ssubstituted by C 4 -C 12 alkyl, phenyl, a-tolylethyl, benzyl, a-methylbenzyl or a,a-dimethylbenzyl, or of a fatty acid having 8 to 22 carbon atoms. A mixture of assistants according to any one of claims 1 to 13, wherein the component is an alkoxylation product of the formula CH 2 -CH 2 H C H \m in which m is 1 to 3 and n 3 is 12 to -21- 16. A mixture of assistants according to any one of claims 1 to 13, wherein the component is a compound of the formula R'-O-alkylcnc-O)- CO-T ni in which R' is an alkyl or alkenyl radical having in each case 8 to 24 carbon atoms or is a radical of the formula 6(a) (Y)m and T is an aliphatic radical having 8 to 30 carbon atoms and Y, m, n I and "alkylene" are as defined in claim 1. 17. A mixture of assistants according to any one of claims 1 to 13, wherein the component is a compound of the formula O/ OO-alkylene- O- CH20-- CHCH 2 CO- T (Y)m ii in which T is an aliphatic radical having 8 to 30 carbon atoms and z is 1 to 25 and Y, m, nj and "alkylene" are as defined in claim 1. 18. A mixture of assistants according to any one of claims 1 to 13, wherein the component is a compound of the formula O---CH 2 CH20-- CH-CH- OH S I I zl Z 2 in which R" is alkyl or alkenyl having in each case 8 to 22 carbon atoms, one of Z 1 and Z 2 is phenyl and the other is hydrogen and s is 4 to 19. A mixture of assistants according to any one of claims 1 to 18, which contains, relative to the whole mixture, 20 to 70 per cent by weight of the component 15 to 40 per cent i. i 1. I I 1 22 by weight of the component and 15 to 40 per cent by weight of the component A process for dyeing textile material containing polyester fibres by means of disperse dyes, which comprises dyeing the material in the presence of the mixture of assistants according to any one of claims 1 to 19.
- 21. A mixture of dyeing assistants, substantially as hereinbefore described with reference to any one of the Examples.
- 22. A process for dyeing textile material containing polyester fibres by means of disperse dyes, which comprises dyeing the material in the presence of the mixture of assistants according to claim 21. 23 Textile material whenever dyed by the process of claim 20 or 22. DATED this TENTH day of OCTOBER 1990 Ciba-Geigy AG Patent Attorneys for the Applicant SPRUSON FERGUSON 6o 1 0s t o *0 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH641/89 | 1989-02-22 | ||
| CH64189 | 1989-02-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU5002590A AU5002590A (en) | 1990-08-30 |
| AU605705B2 true AU605705B2 (en) | 1991-01-17 |
Family
ID=4191747
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU50025/90A Ceased AU605705B2 (en) | 1989-02-22 | 1990-02-21 | Mixture of assistants and its use in the dyeing of polyester fibre materials |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0414631A1 (en) |
| JP (1) | JPH02259173A (en) |
| AU (1) | AU605705B2 (en) |
| CA (1) | CA2010406A1 (en) |
| IL (1) | IL93450A0 (en) |
| MX (1) | MX172152B (en) |
| ZA (1) | ZA901308B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU638793B2 (en) * | 1990-02-14 | 1993-07-08 | Ciba Specialty Chemicals Holding Inc. | Process for dyeing wool with reactive dyes |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE110425T1 (en) * | 1989-02-08 | 1994-09-15 | Ciba Geigy Ag | MIXTURE OF AID AND ITS USE IN DYEING OF SYNTHETIC FIBER MATERIALS. |
| US6159836A (en) * | 1994-09-16 | 2000-12-12 | Stmicroelectronics, Inc. | Method for forming programmable contact structure |
| DE19638566A1 (en) * | 1996-09-20 | 1998-03-26 | Clariant Gmbh | Use of aryloxypolyglycol ethers as leveling and dispersing agents |
| DE102005013781A1 (en) * | 2005-03-22 | 2006-09-28 | Basf Ag | Process for dyeing textiles with vat dye |
| JP5230338B2 (en) * | 2008-10-07 | 2013-07-10 | 第一工業製薬株式会社 | Leveling agent for polyester fiber |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1346622A (en) * | 1963-01-24 | 1963-12-20 | Bayer Ag | Unison Agents |
| DE1769210A1 (en) * | 1968-04-20 | 1970-12-17 | Bayer Ag | Printing and coloring processes |
| DE2732732C3 (en) * | 1977-07-20 | 1980-03-27 | Bayer Ag, 5090 Leverkusen | Aqueous dye dispersions and their use |
| JPS602433B2 (en) * | 1979-04-28 | 1985-01-21 | 一方社油脂工業株式会社 | Dyeing method for polyester synthetic fibers |
| EP0033715A1 (en) * | 1980-01-31 | 1981-08-12 | Ciba-Geigy Ag | Auxiliary and its use in the dyeing or optical brightening of polyester fibre materials |
| JPS6183267A (en) * | 1984-10-01 | 1986-04-26 | Toray Ind Inc | Ink composition for ink jet dyeing and dyeing method using same |
-
1990
- 1990-02-13 EP EP90810099A patent/EP0414631A1/en not_active Withdrawn
- 1990-02-20 IL IL93450A patent/IL93450A0/en not_active IP Right Cessation
- 1990-02-20 MX MX019586A patent/MX172152B/en unknown
- 1990-02-20 CA CA002010406A patent/CA2010406A1/en not_active Abandoned
- 1990-02-21 AU AU50025/90A patent/AU605705B2/en not_active Ceased
- 1990-02-21 ZA ZA901308A patent/ZA901308B/en unknown
- 1990-02-22 JP JP2039904A patent/JPH02259173A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU638793B2 (en) * | 1990-02-14 | 1993-07-08 | Ciba Specialty Chemicals Holding Inc. | Process for dyeing wool with reactive dyes |
Also Published As
| Publication number | Publication date |
|---|---|
| AU5002590A (en) | 1990-08-30 |
| JPH02259173A (en) | 1990-10-19 |
| CA2010406A1 (en) | 1990-08-22 |
| MX172152B (en) | 1993-12-06 |
| ZA901308B (en) | 1990-10-31 |
| IL93450A0 (en) | 1990-11-29 |
| EP0414631A1 (en) | 1991-02-27 |
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