CH676367A5 - Low-foaming prepn. for synthetic fibre finishing - Google Patents

Abstract

Prepn. (I) for finishing synthetic fibres contains 15-84 wt.% dye, optical brightener or UV-absorber which is insol. or sparingly soluble in water (II), 15.5-75 wt.% dispersing agent(s) (III) and 0.5-10 wt.% alkylene diamide (IV). (I) is mfd. by milling the components together in aq. suspension and drying the resulting aq. dispersion. (II) is a dispersion dye, an optical brightener of the stilbene, distyrylbenzene, diphenylstyryl, triazine, benzoxazole, bis-benzoxazole, bis-benzoxazolylthiophen, bis-benzoxazolylnaphthalene, pyrene, coumarin or naphthalene-peri-dicarboxylic acid imide type or a UV-absorber of the benzophenone, 2-hydroxyphenyl-s-triazine or 2-phenylbenztriazole type; pref. UV-absorber has the formula (A) (with R1 = Hal or lower alkyl or alkoxy; R2, R3 = H, Hal or lower alkyl or alkoxy); (III) is a lignin sulphonate, a condensation prod. of naphthalene-, naphthol- or naphthylamine-sulphonic acids with formaldehyde or of phenol-sulphonic acids or phenols with formaldehyde and ureas.

Description

CH 676 367 A5

description

The present invention relates to a low-foam preparation for refining synthetic fibers, in particular to a low-foam dye preparation of a disperse dye. 5 The low-foam preparation according to the invention is characterized in that, based on (a) + (b) + (c),

a) 15 to 84 percent by weight of a dye which is sparingly to insoluble in water, optical brightener or UV absorber,

10 b) 15.5 to 75 percent by weight of one or more dispersants and c) 0.5 to 10 percent by weight of an alkylenediamide or mixtures of alkylenediamides.

The preparation expediently contains 18 to 59 percent by weight of component (a), 40 to 75 percent by weight of component (b) and 1 to 7 percent by weight of component (c). 15 Organic or inorganic pigments, vat dyes or especially disperse dyes and other insoluble or poorly soluble dyes can be used as dyes.

The water-insoluble or poorly soluble optical brighteners are compounds or mixtures of compounds e.g. from the class of the stilbenes, distyryl-benzenes, diphenyl-distyryl, triazines, benzoxazoles, bis-benzoxazoles, bis-benzoxazolylthiophenes, bis-benzoxazolylnaph-20 thalines, pyrenes, coumarins or naphthalene-peri-dicarboximides.

The UV absorbers are expediently sparingly to insoluble in water derivatives of the benzophenone series, of 2-hydroxyphenyl-s-triazines or preferably of the 2-phenylbenzotriazole series. Benzotriazole compounds of the formula are particularly preferred

25th

30th

(1)

wherein Ri is halogen, Niederaikyl or Niederaikoxy and Ffe and r3, independently of one another, are each hydrogen, halogen, Niederaikyl or Niederaikoxy.

Preferred among the benzotriazole compounds of the formula (1) are those in which lower alkyl, such as methyl or tert-butyl, R2 is hydrogen or lower alkyl and r3 is hydrogen, chlorine or methyl.

The focus of interest is 2- (2'-hydroxy-5'-methylphenyl) benzotriazole, 2- (2'-hydroxy-3 ', 5'-dimethylpheny!) - benzotriazole, 2- (2'-hydroxy-5- tert-butylphenyl) benzotriazoI, 2- (2'-hydroxy-3-tert.butyl-5'-methylphenyl) -5-chlorobenzotriazole, 2- (2'-hydroxy-3 ', 5'di-tert.butylphenyl) -5-chloro-ben-

40 zotriazole, 2- (2'-hydroxy-5-tert.octylphenyl) benzotriazole, 2- (2'-hydroxy-3 ', 5'-di-tert.amylphenyl) benzotriazole or 2- (2'-hydroxy -3 /, 5'-di-tert.butylphenyl) benzotriazole.

As dispersants are e.g. the known anionic, such as lignin sulfonates, condensation products of naphthalenesulfonic acid and / or naphthol or naphthylamine sulfonic acids with formaldehyde, condensation products of phenolsulfonic acids and / or phenols with formaldehyde and urea into consideration.

Suitable dispersants are

- condensation products of naphthalenesulfonic acid and formaldehyde

- Condensation products from sulfonated mononuclear phenols and formaldehyde

- Condensation products from dinuclear uncondensed, mono- or bifunctional phenols 50 and formaldehyde

- Condensation products from sulfonated mononuclear phenols, formaldehyde and sulfite

- Condensation products from phenols, naphtholsulfonic acids, sodium sulfite and formaldehyde, in particular from cresol, 2-naphthol-6-sulfonic acid, sodium sulfite and formaldehyde.

Also particularly suitable as dispersants are sulfonated condensation products which, by reacting an aromatic compound having at least two replaceable nuclear hydrogen atoms in any order with a compound of the formula

60 (2)

y

\ / \ /

where X is the direct bond or oxygen,

Shark is chlorine or bromine and 65 n is 1 to 4 and sulfonation has been obtained.

- (CHZ-Hal) n

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CH 676 367 A5

These sulfonated condensation products preferably correspond to the formula

/ \ • •

I II

v *

(3)

3 ^ (CH2-A) n s \ • «

I II • •

V -

(so3m)

p in which X is the direct bond or oxygen, A is the residue of an aromatic compound which is bonded to the methylene group by means of a ring carbon atom, M is hydrogen, alkali metal, alkaline earth metal or an ammonium group and n and p each represent a number from 1 to 4.

N and p are preferably 1 or 2, or they can each be any fractional number from 1 to 4, for example 1,4,1,8,2,1 or 3,2.

Preferred starting materials of formula (2) are chloromethyl diphenyl and chloromethyl diphenyl ether. These compounds are mostly mixtures of isomers with 1 to 3 chloromethyl groups, e.g. the chloromethyl groups are preferably in the o- and p-positions of the two benzene rings. Accordingly, the corresponding sulfonated condensation products are generally present as mixtures, in particular of mono- to tri-substituted diphenyl or diphenyl ether products. Depending on the starting materials and the chosen reaction conditions in the production of the condensation products, the ratio of the isomers to one another changes. If n is 1, p-isomers are used in proportions of e.g. 30 to 90% and o-isomers in proportions of e.g. Get 70 to 10%. If n is 2, e.g. p, p'-, o.o - or o, p'-connections.

These sulfonated condensation products and their preparation are described in DE-OS 2 353 691. Further details can be found in this published specification.

The dispersants can be used in pure form, in industrial mixtures or in the mixture of various components.

An example of a mixture of various components is the advantageous use of 3 to 30 percent by weight, based on the dispersion mixture, of the sulfonated condensation products of the formula (3) mentioned in a mixture with lignin sulfonates and condensation products of naphthalenesulfonic acid with formaldehyde. The weight ratio of the lignin sulfonates to the formaldehyde / sulfonaphthalene condensation products is expediently 10: 1 to 3: 1, preferably 6: 1 to 4: 1.

Sulfated or phosphated adducts of 15 to 100 moles of ethylene oxide or preferably propylene oxide with polyhydric aliphatic alcohols such as e.g. Ethylene glycol, glycerol or pentaerythritol or amines having 2 to 9 carbon atoms and having at least two amino groups or an amino group and a hydroxyl group and alkylsulfonates preferably having 10 to 20 carbon atoms in the alkyl chain, alkylbenzoisuifonates having a straight-chain or branched alkyl chain and preferably having 8 to 20 carbon atoms in the alkyl chain, such as Nonyl or dodecylbenzenesulfonate, 1,3,5,7-tetramethyloctyl-benzenesulfonate or octadecylbenzenesulfonate as well as alkylnaphthalenesulfonates or sulfosuccinic acid esters, e.g. Sodium dihexyl sulfosuccinate or sodium dioctyl sulfosuccinate.

In particular, alkylene diamides of the formula come as component c)

(4) R'-CO-NH-Q-NH-CO-R "

in which R 'and R ", independently of one another, each represent an aliphatic radical having 9 to 23 carbon atoms and Q is an alkylene radical having 1 to 8, preferably 1,2 or 3, carbon atoms.

Component c) can be present as a single compound or in the form of a mixture.

The aliphatic radicals R 'and R "can be straight-chain or branched. Together with the CO group, they advantageously represent the acid radical of an unsaturated or preferably saturated aliphatic carboxylic acid having 10 to 24 carbon atoms. Examples of aliphatic carboxylic acids are capric, lauric, Coconut fatty, myristic, palm kernel fatty acid, palmitic, tallow fatty, oleic, ricinoleic, linoleic, linolenic, stearic, arachidic, arachidonic, behenic, erucic or lignoceric acid are mentioned, behenic acid and especially stearic acid are preferred .

Mixtures of these acids, such as those obtained from the cleavage of natural oils or fats, can also be used. Coconut fatty acid, palm kernel fatty acid, palmitic / stearic acid3

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CH 676 367 A5

Mixtures, tallow fatty acid and arachine / behenic acid mixtures are particularly preferred mixtures.

Preferably R 'and R "each represent an alkyl radical with 9 to 23 carbon atoms and in particular with 15 to 21 carbon atoms.

Q represents in particular an alkylene group which contains 2 to 5 carbon atoms and can be straight-chain or branched. These are, for example, the -CH2CH2-, -CH2CH2CH2-,

Typical representatives for component c) are methylene-bis-stearic acid amide, ethylene-bis-stearic acid reamide or ethylene-bis-behenic acid amide.

The preparation according to the invention expediently contains at least 1.5 percent by weight of component c), based on the mixture of components a) + b) + c). However, it is preferable to use 2 to 5 percent by weight in order to achieve a stable and clearly low-foaming preparation.

Depending on the component (a) used, the preparation according to the invention can, in addition to components (a), (b) and (c), alkali carbonates, such as e.g. anhydrous sodium or potassium carbonate, electrolytes such as e.g. Sodium chloride or sodium sulfate, sodium dithionite, emulators, glycols, block polymers and other anti-foaming agents such as e.g. C8-C22 fatty alcohols, C8-C22 fatty acids or their salts, or polypropylene glycols. It can contain up to about 25 percent by weight, but preferably not more than 15 percent by weight of these other additives. The preparation can also contain up to 10% by weight of water as residual moisture.

Preferred preparations contain, each based on the preparation

20 to 40 percent by weight of component (a)

50 to 70 percent by weight of component (b) individually or as a mixture of two or three dispersants

1 to 5 percent by weight of component (c)

3 to 8 percent by weight of water and 0 to 15 percent by weight of the other additives.

The preparation appropriately contains the alkylenediamide (component c)) in finely dispersed form. The alkylenediamide is dispersed in a known manner by the action of high shear forces on component (a) in the presence of the dispersants, e.g. by kneading in kneaders or by grinding an aqueous suspension in a ball, sand or pearl mill. The kneaded material or aqueous dispersion obtained is dried in a known manner, e.g. in drying cabinets or by spray drying. Another possible use of the alkylenediamide is that the alkylenediamide is first wet-ground with a dispersant and the aqueous dispersion obtained is added tel quel or after spray drying the liquid or powdered preparation, which contains, in particular, a dye as component (a).

Depending on component (a), the preparation according to the invention is used for dyeing or optically brightening synthetic fibers, in particular polyester fibers and / or textile material containing cellulose fibers. As polyester fiber material e.g. Cellulose ester fibers, such as CeIlulose-2 1/2-acetate fibers and triacetate fibers and particularly linear polyester fibers. Linear polyester fibers are to be understood as synthetic fibers which e.g. can be obtained by condensation of terephthalic acid with ethylene glycol or of isophthalic acid or terephthalic acid with 1,4-bis (hydroxymethyl) -cy-clohexane, and also copolymers of terephthalic and isophthalic acid and ethylene glycol. The linear polyester used almost exclusively in the textile industry so far consists of terephthalic acid and ethylene glycol. The dyeing process or optical brightening is carried out in the usual way. The preparation is slowly introduced into a pre-sharpened aqueous bath with stirring, after which the liquor is ready for dyeing or optical brightening. UV absorber dispersions can also be used as auxiliaries in the dyeing of synthetic fibers, in particular polyester fibers or else acid-modified polyester fibers.

It is already known, anti-foaming agent! add to the formulations. The previous commercial form additives for foam regulation have only a partial effect or cannot be incorporated homogeneously, which can cause stains and irregularities e.g. during dyeing. Surprisingly, however,

-CH2-CH-CH3

; "ï

c:

or

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CH676 367 A5

NEN pull-out dyeings and pad dyeings can be carried out with little foam using the preparations according to the invention.

In the following examples, the percentages given are by weight unless otherwise specified. Parts are parts by weight.

example 1

A dye preparation consisting of 318 parts of a disperse dye of the formula

.-. z01

N02— ^ N = N— ^ / S ° 2

\,

'Cl

422 parts of lignin sulfonate,

100 parts of a condensate of formaldehyde and the sodium salt of naphthalenesulfonic acid,

100 parts of the biphenylmethyl-naphthalenesulfonic acid prepared according to Example 3 of DE-OS 2 353 691.

re as sodium salt

30 parts of N, N'-ethylene bisstearamide and 60 parts of water as residual moisture is obtained by wet grinding all components in an open ball mill up to an average particle diameter of 1-2 μm and subsequent spray drying of the aqueous dispersion.

0.6 g of the powder is dispersed in 250 ml of deionized water. The foam test on this dispersion according to the Pretema Jet method shows no foam at 30 °, 60 ° and 120 ° C. On the other hand, if you use the same method to produce a preparation that does not contain N.N'-ethylene bisstearamide, the foam test on the dispersion of 0.6 g powder in 250 ml deionized water gives the following results:

at 30 ° C 100 mm foam height 60 ° C 100 mm S foam height 120 ° C 100 mm foam height.

Example 2

a) A dye preparation consisting of 264 parts of a disperse dye of the formula

CH3 — GHz — S - n —N = N (\ Jî_cH2-y \

s • = »• = •

NHCOCH3

450 parts of lignin sulfonate,

100 parts of a condensate of formaldehyde and the sodium salt of naphthalenesulfonic acid, 120 parts of the biphenylmethyl-naphthalenesulfonic acid prepared according to Example 3 of DE-OS 2 353 691 as sodium acid

6 parts of a propylene oxide / ethylene oxide block polymer having a molecular weight of 3000 and 60 parts of water as residual moisture is obtained by wet grinding all components in an open ball mill up to an average particle diameter of 1-2 μm and subsequent spray drying of the aqueous dispersion.

b) 37 parts of a preparation which consists of 570 parts of N, N'-ethylene bisstearamide,

380 parts of a condensate of formaldehyde and the sodium salt of naphthalenesulfonic acid and 50 parts of water exist and are obtained by wet grinding of the components in an open ball mill up to an average particle diameter of 1-2 μm and subsequent spray drying.

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CH 676 367 A5

0.6 g of this powder is dispersed in 250 ml of deionized water. The foam test on this dispersion according to the Pretema Jet method gives the following results at 30 ° C 10 mm foam height 60 ° C 0 mm foam height 120 ° C 0 mm foam height.

If 0.6 g of the powder obtained in a) is dispersed, the foam test gives the following results:

at 30 ° C 100 mm foam height 60 ° C 100 mm foam height 120 ° C 50 mm foam height.

Example 3

a) A dye preparation which consists of 510 parts of a disperse dye of the formula

Ï1

S ~ \ / ~ \ / C2H * CN

• = • C2Hv-0-C2Hi * CN

440 parts of a lignin sulfonate,

40 parts of a preparation of 500 parts of N, N'-ethylene bisstearamide,

120 parts of a condensate of formaldehyde and the sodium salt of naphthalenesulfonic acid, 330 parts of a ligninsulfonate and 50 parts of water (residual moisture),

20 parts of a propylene oxide / ethylene oxide block polymer (molecular weight 3000) and 48 parts of water (residual moisture)

is composed, is obtained by wet grinding of all components in an open ball mill up to an average particle diameter of 1-2 μm and subsequent spray drying of the aqueous dispersion.

0.6 g of this powder is dispersed in 250 ml of deionized water. The foam test on this dispersion using the Pretema jet method gives the following results:

at 30 ° C 20 mm foam height 60 ° C 10 mm foam height 120 ° C 0 mm foam height.

b) If, on the other hand, a preparation is prepared using the same method that does not contain N, N'-ethylene bisstearamide, the foam test on the dispersion of 0.6 g powder in 250 ml deionized water gives the following results:

at 30 ° C 95 mm foam height 60 ° C 100 mm foam height 120 ° C 70 mm foam height.

Example 4

Be in a sand mill

40 parts of 2- (2-hydroxy-3'-tert-butyl-5'-methylphenyl) -5-chlorobenzotriazole

10 parts of ammonium salt of the sulfuric acid ester of the adduct of 60 mol of propylene oxide with 1 mol of glycerol

1 part of an oxyalkylation product with 25 ethylene oxide units of a Ci6 / Ci8 alcohol, 3 parts of N ', N'-ethylene bisstearamide and 46 parts of water.

The mixture is then ground with quartz sand until the particle size is <5 μm. The dispersion is separated from the grinding sand.

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CH676 367 A5

75 parts of the dispersion obtained with stirring

12.5 parts of a 2% aqueous solution of a biopolymer based on polysaccharide and 12.5 parts of water mixed and homogenized.

Example 5

Be in a sand mill

40 parts of a mixture of 1,2-bis (5-methylbenzoxazoI-2-yl) ethylene and 2,4-dimethoxy-6- (1-pyrenyl) -1,3,5-triazine

2 parts of sodium dihexyl sulfosuccinate 4 parts of a polyaddition product of 80% ethylene oxide and 20% propylene oxide; Molecular weight about 10,000 to 15,000

4 parts of N ', N'-ethylene bisstearamide mixed 40 parts of water.

The mixture is then ground with quartz sand until the particle size is <3 (im. The dispersion is separated from the grinding sand.

50 parts of the dispersion obtained are mixed with stirring and 15 parts of a 10% solution of a polyvinyl alcohol, 0.5 parts of formaldehyde and 34.5 parts of water and homogenized.

Application example 1

100 parts of the preparation prepared according to Example 1 are dispersed in 900 parts of water. This foam-free liquor is used to block a polyester / cotton fabric with a liquor absorption of 70%, then subject the fabric to intermediate drying and then thermosolate at 210 ° C. for 1 minute. A level yellow coloration is obtained which has no spots.

Application example 2

100 g of a knitted polyester fabric (polyethylene glycol terephthalate) are placed in 3 liters of water in an HT circulation apparatus at 60 ° C.

9 g ammonium sulfate

18 g of disodium salt of di '(6-sulphonaphthyI-2-) methane

5 g of a finely dispersed dye of the formula

3 g of the UV absorber formulation prepared according to Example 4 contains and is adjusted to pH 5 with 85% formic acid. The dye bath is heated to 130 ° C. in the course of 30 minutes with a constantly circulating liquor and dyeing at this temperature for 1 hour. The dyebath is then cooled and the substrate is rinsed and, as usual, reductively cleaned to remove unfixed dye. The substrate is then neutralized, rinsed again and dried. Due to the stable UV absorber formulation used, no increase in the differential pressure is detected during the dyeing process, nor are there any deposits in the interior of the winding body. This gives a uniform, lightfast, navy blue color.

Claims (1)

Claims 1. Low-foam preparation for the refinement of synthetic fibers, characterized in that, based on (a) + (b) + (c) (a) 15 to 84 percent by weight of a sparingly to insoluble dye, optical brightener or UV absorber, (b) 15.5 to 75 percent by weight of one or more dispersants and ? S \ / \ / ^ I II 11 1 m. t • • il il i »• • • V V E UH 7 5 10th 15 20th 25th 30th 35 40 45 50 55 60 65 CH 676 367 A5 (e) contains 0.5 to 10 percent by weight of an alkylene diamide or mixtures of alkylene diamides. 2. Preparation according to claim 1, characterized in that the dye is a disperse dye. 3. Preparation according to claim 1, characterized in that the optical brightener from the class of the stilbene, distyryl-benzenes, diphenyldistyryls, triazines, benzoxazoies, bis-benzoxazoles, bis-benzoxazolyithiophenes, bis-benzoxazolylnaphthalenes, pyrenes, coumarins and naphthalene peri- dicarboxylic acid imides. 4. Preparation according to claim 1, characterized in that the UV absorber is a sparingly to insoluble in water derivative of the benzophenone series, of 2-hydroxyphenyI-s-triazines or the 2-phenylbenzotriazole series. 5. Preparation according to one of claims 1 to 4, characterized in that it contains as dispersant (b) lignin sulfonates, condensation products of naphthalenesulfonic acid or naphtholsulfonic acid or naphthylamine sulfonic acid with formaldehyde or condensation products from phenolsulfonic acid or phenols with formaldehyde and ureas. 6. Preparation according to one of claims 1 to 4, characterized in that the dispersant of the formula (3) in which X is the direct bond or oxygen, A is the residue of an aromatic compound which is bonded to the methylene group by means of a ring carbon atom, M is hydrogen, alkali metal, alkaline earth metal or an ammonium group and n and p each represent a number from 1 to 4. 7. Preparation according to one of claims 1 to 4, characterized in that the dispersant is a mixture of lignin sulfonates, condensation products of naphthalenesulfonic acid and formaldehyde and a compound of formula (3) according to claim 6. 8. Preparation according to one of claims 1 to 4, characterized in that it contains alkylsulfonates, alkylnaphthalenesulfonates or sulfosuccinic acid esters as dispersants. 9. Preparation according to one of claims 1 to 8, characterized in that component (e) is an alkylenediamide of the formula R'-CO-NM-Q-NM-CO-R " is, in which R 'and R ", independently of one another, each represent an aliphatic radical having 9 to 23 carbon atoms and Q is an alkylene radical having 1 to 8 carbon atoms. 10. A process for the preparation of the preparation according to claim 1, characterized in that the dye, the optical brightener or the UV absorber of component (a), the dispersant or dispersants (b) and the alkylenediamide or mixtures of alkylenediamides (c) grinds in the form of an aqueous suspension and the aqueous dispersion obtained dries. I Ii • • * • '• l ii - (ch2-a) - (so3h) 8th