DE1955071A1 - Process for the continuous dyeing of synthetic fiber materials - Google Patents

Description

COLOR FACTORY BAYERAG

LEVERKUSEN-Btyetwerk October 30, 1969 Patent department B / HM

Process for the continuous dyeing of synthetic fiber materials -

The invention is a process for continuous Dyeing of synthetic fiber materials from organic solvents; the procedure is characterized by that the fiber materials are impregnated with dye liquors, the anthraquinone dyes of the formula

X

COOB) _n

included in the

R for a hydroxyl or amino group and R ₁ for a hydrogen atom, a chlorine or bromine atom, a phenyloxy, phenylthio group or a group of the formula

, -SB ₁ or -S-

stand
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C *

X represents a hydrogen atom or a hydroxyl group or one X stands for a hydroxyl group and the other X stands for a nitro or amino group,

Rp hydrogen or a C-j-Cz-alkyl or O ^ -C ^ -

Alkoxy group
^ m and η independently of one another mean 1 or 2 and

B and B ₁ independently of one another represent a G ^ -C ^ g-alkyl, in particular 0.-C ₁ g-alkyl, cycloalkyl or aralkyl radical,

with the proviso that the total of the total _{carbon atoms contained in the substituent (s) B and B 1} is at least 4 and at most 18,

and then subjected to a heat treatment.

Examples of B and B ₁ include: Cj-CjQ-alkyl radicals of methyl, ethyl, propyl, iso-propyl, η-butyl, iso-butyl, sec-butyl and tert-butyl -, n-pentyl, iso-amyl, sec-pentyl, neopentyl, n-hexyl, methyl pentyl, dimethyl butyl, n-heptyl, methyl hexyl, dimethyl pentyl , Trimethyl-butyl-, n-octyl-, iso-octyl-, methyl-heptyl-, dimethyl-hexyl-, trimethyl-pentyl-, tetramet hy1-butyl-, n-nonyl _T , iso-nonyl-, dimethyl-heptyl -, trimethylhexyl, decyl, undecyl, dodecyl, 2,2-dimethyldecyl, tetradecyl, hexadecyl and octadecyl radical;

as cycloalkyl radicals of cyclohexyl, methylcyclohexyl and 4-tert-butylcyclohexyl radical

as aralkyl radicals, in particular the benzyl and dero <, d-dimethylbenzyl radical as well as the dodecylbenzyl radical.

As alkylthio groups for R _{1, there} may be mentioned -SB ₁ C ₁ -C ₁₂ -alkylthio groups such as the methyl, ethyl, i-propyl, 2-ethylhexyl and the dodecylthio group.

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The dyes used according to the invention for dyeing from organic solvents are obtained by processes known per se, for example by reacting leuco-1,4-dihydroxy- or leuco-1,4-diamino-anthraquinones, nitro-hydroxy-anthraquinones or amino-halogen-anthraquinones with aminoaryl _t the one or more, preferably 2-19 carbon atoms carry Carbonsäurealkyl- containing alkyl, cycloalkyl or -aralkyl radicals.

Suitable organic solvents for the process according to the invention are those solvents which are essentially immiscible with water and whose boiling points are between 40 and 150 ^° C., e.g. B. aromatic hydrocarbons, such as toluene or xylene, aliphatic halogenated hydrocarbons, in particular chlorinated hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, trichloroethane, tetrachloroethane, dichloropropane, chlorobutane, dichlorobutane and fluorohydrocarbons such as dichlorofluorocarbons and fluorohydrocarbons such as per-chloro-fluorohydrocarbons and aliphatic peroxide n-hexane, 1,2,2-trifluorotrichloroethane and trifluoropentachloropropane, aromatic chlorine and fluorocarbons, such as chlorobenzene, fluorobenzene, chlorotoluene and benzotrifluoride.

Tetrachlorethylene, trichlorethylene, 1,1,1-trichloroethane and 1,1,1-trichloropropane. Mixtures of these solvents can also be used.

In the case of those to be colored by the process according to the invention Synthetic fiber materials are, in particular, fiber materials made of polyesters, e.g. B. rolyäthylenterephthalate, Polyester from 1,4-bis- (hydroxymethyl) -cyclohe3can and Terephthalic acid or polycarbonates from 2,2-Bi8- (p-hydroxyphenyl) propane, from cellulose triacetate, from synthetic polyamides, such as poly - ^ - caprolactam, polyhexamethylene diamine adipate or poly-M ^ aminoundecanoic acid, from polyurethanes or Le A 12 609 - 3 -

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made of polyolefins. The fiber materials can be in the form of Woven and knitted are available.

For dyeing, the dyes to be used according to the invention are dissolved in the organic solvents, which are essentially immiscible with water, or puts them in the form of Solutions in solvents that are infinitely miscible with these solvents, such as alcohols, dimethylformamide, dimethylacetamide, Dimethyl sulfoxide or SuIfolan, to and impregnated with the clear dye solutions obtained, which may still be soluble to improve the levelness of the dyeings non-ionic auxiliaries, e.g. B. the well-known interfacial

^ active oxyethylation and propoxylation products of fatty alcohols, alkylphenols, fatty acid amides and fatty acids, which may contain synthetic fiber materials. The dyes are then fixed on the fiber materials by means of a heat treatment. The heat treatment can in a short term dry heat treatment at 120 - consist 230 ⁰ C, the dry heat treatment -wherein optionally an intermediate drying can be preceded, or in a treatment of the fiber materials in superheated solvent vapor 100-150 ⁰ C. Differential unfixed Färbstoffanteile can be prepared by brief treatment with the cold, organic solvent wash out. It should be noted that mixtures of the to be used according to the invention

| l Dyes sometimes give a better color yield than the individual dyes and, if appropriate, even better solubility in the organic medium.

With the help of the method according to the invention it is possible to Dyeing from organic solvents on synthetic fiber materials to achieve dyeings that are characterized by high levels of dye yield, very good structure and excellent fastness properties, especially very good thermosetting, washing, Rubbing and light fastness properties. Another advantage

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of the dyes to be used according to the invention is their high level Solubility in organic solvents, 'especially in tetrachlorethylene, trichlorethylene, 1,1,1-trichloroethane and 1,1,1-trichloropropane, which in particular allows the Dyeing can also be carried out without the use of solubilizers.

The parts given in the following examples are parts by weight.

example 1

A fabric made of polyethylene terephthalate fibers is at room temperature impregnated with a clear blue solution that

10 parts of 1. 5-I) ίhydroxy-4 ■ - (3- ■ isoamyloxycarbonylanilino) -8-nitro-anthraquinone tetrachlorethylene in 990 parts

contains. After squeezing to a weight increase of 60 io , the fabric is ^{dried at 80 °} C. for one minute. The dye is then by 45-second heating the fabric at 190 - 220 ⁰ C is fixed. The small amount of non-fixed dye is then washed out by briefly treating for 20 seconds in cold tetrachlorethylene. After drying, a clear blue dyeing is obtained which is distinguished by its high dye yield, very good structure and excellent fastness properties, in particular very good heat-setting, washing, rubbing and light fastness properties.

In an analogous manner, equivalent clear blue colorations were obtained also look at fabrics

a) cellulose triacetate,

b) synthetic polyamides or polyurethanes and c) polypropylene fibers

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obtain; just got the thermal insulation

for a) at 200 - 220 ⁰ G,
for b) at 170 - 200 ⁰ G and for c) at 120 - 150 ⁰ C

performed.

Equivalent colorations were also obtained when the 990 parts of tetrachlorethylene were replaced by the same amount of one of the the following solvent has been replaced: methylene chloride, chloroform, carbon tetrachloride, dichloroethane, trichloro ^ ethane, trichlorethylene, tetrachloroethane, dichloropropane, 1,1,1-trichloropropane, pentachloropropane, ghlorbutane, dichlorobutane, Dichlorohexane, perfluoro-n-hexane, 1,2,2-trifluorotrichloroethane and trifluoropentachloropropane.

The dye used was made as follows:

15 parts of 1 .S-dihydroxy ^ .e-dinitro-anthraquinone and 26 parts of isoamyl 3-aminobenzenate were dissolved in 25 parts of glycol monoethyl ether

Heated to the boil until the starting material was no longer detectable by chromatography. After cooling, the melt was introduced into a mixture of 25 parts of concentrated hydrochloric acid and 400 parts of ice. The deposited precipitate was filtered off with suction, washed and dried. Yield of 1,5-dihydroxy-4- (3-isoamyloxycarbonylanilino) -8-nitro- anthracMnon: 95 Ί » the theory.

Example 2

A knitted fabric made of polyhexamethylene diamine adipate threads is impregnated at room temperature with a clear blue solution which

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10 parts of 1.8-dihydroxy-4- (3-isoamyloxycarbonyl-

anilino) -5-nitro-anthraquinone and 7 parts of nonylphenolheptaethylene glycol ether in 983 parts of tetrachlorethylene

contains. After squeezing off to a weight increase of 60 io , the knitted fabric is ^{dried at 80 °} C. for 1 minute. The dye is then fixed by 45 sektindiges heating the fabric to 192 ⁰ C. Then, by briefly treating in cold tetrachlorethylene, small amounts of non-fixed dye are washed out. After drying, a blue dyeing is obtained which is distinguished by its high dye yield, very good structure and excellent fastness properties, in particular very good heat-setting, washing, rubbing and light fastness properties.

An equivalent coloration was also obtained if the same amount was used instead of the 983 parts of tetrachlorethylene Toluene, xylene, chlorobenzene or chlorotoluene was used.

Example 3

A fabric made of cellulose triacetate fibers is impregnated at room temperature with a clear blue solution which

10 parts of 1,5-dihydroxy-4- (3-2'-ethylbutoxy-

carbonylanilino) -8-nitro-anthraquinone and 7 parts of nonylphenol heptaethylene glycol ether in 983 parts of tetrachlorethylene

contains. After the squeezing off to a weight increase of 60 io, the fabric is dried for 1 minute at 8O ⁰ C. The dye is then fixed by heating the tissue to 215 ° C. for 1 minute. A clear blue coloration is obtained, which is very evident due to the high dye yield

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good structure and excellent fastness properties, in particular very good heat-setting, washing, rubbing and light fastness properties excels.

The used as dye 1. S-butoxycarbonylanilino ^ S-nitro-anthraquinone was prepared in the same way as described in Example 1, only. that instead of 26 parts of 3-amino-benzoic acid isoamyl ester the equivalent amount of 2'-ethylbutyl 3-aminobenzoate was used.

Example 4

P A fabric made of poly-1 ^ -cyclohexanedimethylene terephthalate is impregnated at room temperature with a clear blue-violet solution which

10 parts of 1,5.8-trihydroxy-4- (3-2.2'-dimethylhexoxy-

carbonylanilino) anthraquinone in 990 parts of tetrachlorethylene

contains. After squeezing to a weight increase of 60 ia , the dye is fixed by treating the fabric with superheated tetrachlorethylene vapor at 150 ° C. for 35 seconds. Then, it is excluded by a brief rinse in cold tetrachlorethylene the low unfixed Färbstoffanteil W wash. After drying, a blue-violet dyeing is obtained, which is distinguished by its high dye yield, very good structure and excellent fastness properties.

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Example -5 .

A fabric made of polypropylene fibers is impregnated at room temperature with a clear blue solution which

10 parts of 1.8-dihydroxy-4- (3-dodecyloxycarbonyl-

anilino) -5-nitro-anthraquinone and 7 parts of nonylphenolheptaethylene glycol ether in 983 parts of tetrachlorethylene

contains. After squeezing to a weight increase of 60 fo , the fabric is ^{dried at 80 0} C for 1 minute. The dye is then fixed by 30-second heating of the tissue to 14O ⁰ C. Brief treatment in a cold solvent can wash out unfixed dye components. A blue dyeing is obtained which is distinguished by a high dye yield, very good structure and excellent fastness properties, in particular very good heat-setting, washing, rubbing and light fastness properties.

Example 6

A fabric made of anionically modified polyethylene terephthalate fibers (Dacron 64 ^ 5 '), is used at room temperature with a clear blue solution impregnated that

10 parts of 1,5-dihydroxy-4- (3-2 '^' - dimethylbutoxy-

carbonylanilino) -8-nitro-anthraquinone and 7 parts of nonylphenol heptaethylene glycol ether in 983 parts of tetrachlorethylene

contains. After squeezing to a weight increase of 60 io , the fabric is ^{dried at 80 °} C. for one minute. The dye is then by 45-second heating the fabric at 190 - 22O ⁰ C fixed. Then by short

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Rinse with cold tetrachlorethylene to wash out the small amount of non-fixed dye. After drying, one obtains a clear blue color, which is characterized by its high dye yield, very good build-up and excellent fastness properties, in particular very good thermosetting, washing, rubbing and light fastness.

example 7th

A fabric made of anionically modified polyamide fibers (nylon T 844 ^) becomes clear blue at room temperature Solution impregnated that

10 parts of 1.8-dihydroxy-4- (3-2 ^l -äthylhexoxycarbonyl-

anilino) -5-nitro-anthraquinone and 7 parts of nonylphenolheptaethylene glycol ether in 983 parts of tetrachlorethylene

contains. After the squeezing off to a weight increase of 60 fo the tissue for one minute at 80 ⁰ G-dried and the dye is fixed through one-minute heating the fabric to 192 ⁰ G. A clear blue dyeing is obtained, which is distinguished by a high dye yield, very good structure and excellent fastness properties, in particular very good heat-setting, washing, rub and light fastness properties.

example 8th

A fabric made of polyethylene terephthalate fibers is at room temperature impregnated with a clear blue solution that

5 parts of 1,5-dihydroxy-4- (3-isobutoxycarbonylanilino) -8-nitro-anthraquinone and

5 parts of 1.8-dihydroxy-4- (3-2 ^l -äthylbutoxycarbonyl-

anilino) -5-nitro-anthraquinone in 990 parts of 1,1,1-trichloroethane

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contains. After squeezing to a weight increase of 60 fo , the dye is fixed by treating the fabric with superheated 1,1: 1,1-trichloroethane vapor at 140 ^{0 for 45 seconds.} The small amount of non-fixed dye is then washed out by briefly rinsing in cold 1,1,1-trichloroethane. After drying, a clear blue dyeing is obtained, which is distinguished by its high dye yield, very good structure and excellent fastness properties.

Strong blue colors on fabrics made of polyester, triacetate polyamide, Polyurethane and polyolefin fibers with excellent fastness properties were also obtained if instead of the in Examples 1-7 specified dyes are the same Amount of one of the dyes indicated in the following table was used.

example dye

1. S-yy ^ Cy e — nitro-anthraquinone

10 1,5-dihydroxy-4- (4-stearyl-oxycarbonylanilino) -8-nitro-anthraquinone

11 1.8-Mhydroxy-4- (4-methyl-3-hexyloxycarbonylanilino) -5-nitro-anthraquinone

12 1.8-dihydroxy-4- (3-methyl-4-octyloxycarbonylanilino) -Jj-nitro-anthraquinone)

13 1,8-dihydroxy-4- (3-isopropoxy-4-4'-tert-butylcyclohexyloxycarbonyl-anilino) -5-nitro-anthraquinone

14 1.5-3) ihydroxy-4- (3-2-ethylhexoxycarbonylanilino) 8-amino-anthraquinone

15 1.8-I) ihydroxy-4- (3-isoamyloxycarbonylanilino) -5-amino-anthraquinone ^

16 1,5-dihydroxy-4- (4-2 · .2 · -dimethyloctyloxycarbonylanilino) -8-amino-anthraquinone

17 1,5-dihydroxy-4- (4-2'-ethylbutoxycarbonylanilino) -8_amino-anthraquinone

18 1.8-dihydroxy-4- (4-2 '^ "- dimethylhexoxycarbonylanilino) -5-amino-anthraquinone

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Example ; Dye _____

19 1.5-Oihydroxy-4- (2-2 '^' - dimethyldecyloxycarbonylanilino) -S-amino-anthraquinone

20 1,8-dihydroxy-4- (2-decyl-oxycarbonylanilino) -5-aminoanthraquinone

21 1,8-Oihydroxy-4- (2,3-bis- (hexoxycarbonyl) -anilino) -5-amino-anthraquinone

22 1,5-Dihydroxy-4- (3,4-bis- (butoxyearbonyl) -anilino) -8-amino-anthraehinone

23 1 .5-D ± hydroxy-4- (4-ethyl-3-2 '-ethylbutoxycarbonylanilino) -8-amino-antlirachinone

24 1.8-dihydroxy-4- (4-methoxy-3-isononyloxycarbonylanilino) -5-amino-anthraquinone

Example 25

A fabric made from poly-1,4-cyclohexanedimethylene terephthalate is impregnated at room temperature with a clear blue-red solution which

10 'parts 1-hydroxy-4- (3-isoamyloxycarbonylanilino) -

anthraehinon and

7 parts of nonylphenol heptaethylene glycol ether in 983 parts of tetrachlorethylene

contains. After squeezing to an increase in weight of $ 60, the fabric is ^{dried at 80 °} C. for 1 minute. The dye is then by 45-second heating the fabric at 190 - 220 ⁰ C is fixed. Then the small amount of non-fixed dye is washed out by briefly treating for 20 seconds in cold tetrachlorethylene. After drying, a strong blue-violet dyeing is obtained, which is distinguished by its excellent fastness properties, in particular very good heat-setting, washing, rubbing and light fastness properties. -

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The dye used was made as follows:

16 parts of 1 ^ -dihydroxy-anthraquinone, 5 parts of leuco-1,4-dihydroxy-anthraquinone, 12 parts of boric acid and 22 parts of 3-amino-benzoic acid isoamyl ester were stirred in 150 parts of ethanol under nitrogen at 80 ⁰ O until chromatographically none Starting material was more detectable. The resulting dye was filtered off with suction after cooling, washed with hot water and dried. Yield of 1-hydroxy-4- (3-isoamyloxycarbonylanilino) anthraquinone: 90 % of theory.

Strong blue-violet colorations on fabrics made from polyester, triacetate, polyamide, polyurethane and polyolefin fibers with excellent fastness properties were also obtained if instead of the dye indicated in Example 24 the same amount of one of those indicated in the following table Dyes was used.

Example dye

26 1-Hydroxy-4- (3-2 ^ '- dimethylhexoxycarbonylanilino) anthraquinone

27 1-Hydroxy-4- (4-2 -ethylhexoxycarbonylanilino) - ■■ anthraquinone

28 1-Hydroxy-4- (3.5-bis (butoxycarbonyl) anilino) anthraquinone

29 1-Hydroxy-4- (4-methyl-3-2'-ethylbutoxycarbonylanilino) anthraquinone

30 1-Hydroxy-4- (4-ethyl-3-decyloxycarbonylanilino) anthraquinone

31 1-Hydroxy-4- (4-propoxy-3-2'.2'-dimethylbutoxycarbonylanilino) anthraquinone

32 1-Hydroxy-4- (2-methoxy-4-2 · '. 2' -dimethyl-octyloxycarbonylanilino) -anthraquinone

example 33

A fabric made of polyethylene terephthalate fibers is impregnated with a clear blue-red solution at room temperature,

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the

10 parts of 1-amino-4- (3-2 »-ethyl" butoxycarbonyl-: aninilo) anthraquinone in

990 parts of tetrachlorethylene

contains. After squeezed onto a G-60 fo ewichtszunähme of the fabric is 1 minute at 8O ⁰ G dried. Subsequently, the dye is of the fabric to 190 by 60-second heating - 220 ⁰ C fixed and unfixed dye washed out by treating for 20 seconds in cold tetrachlorethylene. After drying, a deep reddish blue dyeing is obtained, which is characterized by its high dye yield, very good structure and very good thermosetting, washing, rubbing and light fastness properties.

If, instead of the dye mentioned in Example 32, the same amount of one of the dyes listed in the table below was used, fabrics made of polyester, triacetate, polyamide, polyurethane or polyolefin fibers were dyed with fastness properties equivalent to those in the table below given color shades:

Example dye hue

34 1-Amino-4- (4-2 '^' - dimethylhexoxy- reddish carbonylanilino) anthraquinone blue

35 1 ~ amino ~ 2-chloro-4- (4-methyl-3-myristyl-reddish oxycarbonylanilino) anthraquinone blue

36 1-Amino-2-bromo-4- (3-isoamyloxy- reddish carbonylanilino) anthraquinone blue

37 1-Amino-2-bromo-4- (4-2'-ethylbutoxy reddish carbpnylanilino) anthraquinone blue

38 1-Amino-2-bromo-4- (2-hexoxycarbonyl-blue-violet anilino) anthraquinone

39 1-Amino-2-butylthio-4- (4-propoxy-reddish carbonylanilino) -anthraquinone blue

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example

dye

hue

40 41 42

43 44 45 46 47 48 49 50

51 52

53 54 55

1-Amino-2-dodecylthio-4- (4-methyl-3-methoxycarbonyl-anilino) -anthraquinone

1-Amino-2-phenoxy-4- (3-2 ·. 2. '-dimethylhexoxycarbonylanilino ) anthraquinone

1-Amino-2- (4-tert-butylphenoxy) -4- (4-isobutoxycarbonylanilino) -anthra chinone *

1-Amino-2- (4-isooctylphenoxy) -4- (3-methoxycarbonylanilino) anthraquinone

1-Amino-2- (3,4-dimethylphenoxy) -4- (3-isoamyloxycarbonylanilino) anthraquinone

1-Amino-2- (4-isoamyloxyphenoxy) -4- (4-ethoxycarbonylanilino) anthraquinone

1-Amino-2- (3.5-diisopropoxyphenoxy) -4- blue-violet (3-propoxycarbonylanilino) anthraquinone

reddish blue

blue-violet

blue-violet

blue-violet blue-violet blue-violet

1-Amino-2-phenylthio-4- (3-isoamyloxycarbonylanilino) anthraquinone

1-Amino-2-phenylthio-4- (4-2'-ethylbutoxycarbonylanilino) anthraquinone

1-Amino-2- (4-methylphenylthio) -4- (3-amyloxycarbonylanilino) anthraquinone

1-Amino-2- (2-methylphenylthio) -4- (4-2 ¹ .2 ^L -dimethylbutoxycarbonylanilino) anthraquinone

1-Amino-2- (4-tert-butylphenylthio) -4- (3-butoxycarbonylanilino) anthraquinone

1-Amino-2- (4-isooctylphenylthio) -4- (4-methoxycarbonylanilino) anthraquinone

1-Amino-2- (4-benzylphenoxy) -4- (3-2'.2'-blue-violet dimethylhexoxycarbonylanilino) -.

anthraquinone

reddish blue

reddish blue

reddish blue

reddish blue

reddish blue

reddish blue

1-amino-2- / 4 "- (2-phenyl-propyl- (2) -phenoxy 7-4- (3-isoamyloxycarbonylanilino) anthraquinone

1-hydroxy-4- (4-2'.3'- or 4'-dodecylbenzyloxycarbonylanilino) anthraquinone

blue-violet

blue-violet

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Claims (5)

Claims 1) Process for the continuous dyeing of synthetic fiber materials from organic solvents, thereby characterized in that the fiber materials are impregnated with dye liquors, the anthraquinone dyes of the formula 0 R included in the R for a hydroxyl or amino group and R ^ for a hydrogen atom, a chlorine or bromine atom. a phenyloxy, phenylthio group or a G group the formula -SB ₁ stands, X denotes a hydrogen atom or a hydroxyl group or P- or one X denotes a hydroxyl group and the other denotes X stands for a nitro or amino group, Rp is hydrogen or a C.-C-z-alkyl or C - C, alkoxy group m and η independently of one another mean 1 or 2 and B and B .. independently of one another for a C ^ -C ^ g Cycloalkyl or aralkyl radical, Le A 12 609 - 16 - 1098 20/20 55 with the proviso that the total of the total _{carbon atoms contained in the substituent (s) B and B 1} is at least 4 and at most 18, and then subjected to a heat treatment. 2) Method according to claim 1, characterized in that that one anthraquinone dyes of the formula X 0 NH used in the one X for a hydroxyl group and the other X stands for a nitro or amino group, R _{2 is} hydrogen or a C ₁ -0, -AllCyI- or Cj-C ^ -alkoxy group means and
B represents a 0, -C ₁₈ -AllEyI- or cycloalkyl radical. 3) Process according to claim t _r, characterized in that one anthraquinone dyes of the formula 0 OH GOOB . 0 NH used in the Le A 12 609 - 17 - ORIGINAL INSPECTED 109 820/2055 R _{2 is} hydrogen or a G ₁ -C, -alkyl- or Cj-G ^ - Alkoxy group means and. B represents a C.-O ^ -alkyl or cycloalkyl radical. 4) Process according to claim 1, characterized in that one anthraquinone dyes of the formula 0 NH ₂ GQOB used in the R _{1 is} a hydrogen atom, a chlorine or bromine atom, a phenyloxy or phenylthio group or a radical of the formula . -SB ₁ or S / ^ ¹ V stands, R ^{1 is} a C | -G, -alkyl or C - C, -alkoxy group, m is 1 or 2 and B stands for a Cj-C-jg-alkyl, cycloalkyl or aralkyl radical j with the proviso that the sum of the total in the bzvr. the carbon atoms contained in the substituents B and B ₁ are at least 4 and at most 18, 5) Synthetic fiber materials, dyed according to claim 1 fcis 4. Le A 12 6Q9 - t8 - 109820/2055