DE2404358A1 - COLORING PROCESS - Google Patents

Description

PATENTANWÄLTE DR.-I NG. H. FIN CKE DIPL.-ING. H. BOHR DIPL.-ING. S. STAEGER

Telephone: '26 60 60

Telegram·! Claims Munich Poitichiclckonto. Munich 27044-802

Bank details Bayer. Vereinibank Munich, account 620 404

Mop. no. 23448 - Dr.Κ / Ρ

Please indicate in t) * your answer

Case Dd. 25831

January 30th

MOIIenlraQe 3i

IMPERIAL CHEMICAL INDUSTRIES LIMITED, London, Great Britain

Dyeing process
Priority: 1/30/1973 - Great Britain

The invention relates to a method of dyeing, and in particular to a method for dyeing polyamide textile materials.

According to the invention there is provided a method for dyeing polyamide textile materials proposed, which is carried out by a polyamide textile material with a aqueous solution of an azo dye of the formula

A-N = N-E

\ - ς, ² - Β ²

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treated, wherein A represents the remainder of a diazo component of the benzene or naphthalene series with the exception of aniline-2,4-disulfonic acid or an alkylated or halogenated derivative thereof; E stands for the remainder of a coupling component of the aminobenzene or aminonaphthalene series, the aminonaphthalene being free from hydroxyl groups; X stands for "N-," C-Cl or "C-CN; Y represents chlorine or bromine; Q is -0-, -S- or -NR-, where R is hydrogen or lower alkyl; Q for a direct bond, -0-, -CO-r »-SO ₂ -, -SO ₂ NH-, -NHSO ₂ -, -CONH-, -NHCO-, -COO-, -OCOr, -OSO ₂ - , -S- or -NR ^ -, where R ^ is hydrogen or lower alkyl; R for an alkylene, cycloalkylene or arylene

p
radical; R stands for an optionally substituted one

Alkyl, cycloalkyl, aralkyl or aryl radical, the-

1 2

art that R and R together do not have more than 15 carbon atoms contain; R ^ stands for hydrogen or lower alkylj where the group -NR ^ - is bonded to E, if not E represents the residue of an i-naphthylamine-8-sulfonic acid or is bonded to a terminal residue in A; and η is an integer from 1 to 3.

The radical represented by A can contain customary substituents such as are suitable for diazo components. Examples of substituents are sulfonic acid and carboxylic acid groups, chlorine, bromine, cyano, hydroxy, alkyl, alkoxy, trifluoromethyl, -NHCOR, where R is an alkyl, aryl, alkoxy, aryloxy, alkylamino, arylamino or amino group, -SOoNR ^ R ⁸ , where R 'is an alkyl or aryl group and R

QQ

Is hydrogen or an alkyl group, and -SO ₂ R ⁷ , where R ^ is an alkyl or aryl group. Other substituents that can be present on A are phenylazo and naphthylazo radicals, which can themselves be substituted. If A carries a phenylazo or naphthylazo radical, then the can

■ χ

Group -NR ^ bound to the phenylazo or naphthylazo radical

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to be, that is, to a terminal residue of the dye molecule, but not to the benzene or naphthalene nucleus, bound to E through a single azo group.

Throughout the specification the term "low" denotes Alkyl "means those alkyl radicals which have 1 to 4 · carbon atoms contain.

1 2 ■

Preferably R is an arylene radical and R is an alkyl radical with 4 to 7 carbon atoms. In these cases it is

Ί 2

Q is preferably oxygen and Q is preferably a direct one Binding.

The dyes of the formula I can be prepared by adding a compound of the formula

■ CD,

(II)

wherein X and Y have the meanings given above, in any order, with equimolecular amounts of one Azo compound of the formula

IiR ³ H

(III)

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in which A, E, R * and η have the meanings given above, and a compound of the formula

r ² -q ² -R ¹ -q ¹ -H

(IV)

12 1 2

wherein R, R, Q and Q have the meanings given above, implements.

The dyes of the formula I can also be prepared by using an aromatic amine other than aniline-2,4-d'isulfonic acid or an alkylated or halogenated derivative thereof is diazotized and the diazo compound thus obtained with a coupling component of the aminobenzene or aminonaphthalene series with the exception of an aminonaphthole, where the amine and the coupling component together have η sulfonic acid groups and a group of the formula

(V)

contain, in which n, X and Y have the meanings given above, where a dye of the formula

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which is then directly connected to a connection of the. Formula IV is implemented, except when R is an alkylene or cycloalkylene radical and Q is -O- or -S-.

Suitable compounds of the formula II are cyanuric chloride, cyanuric bromide, 2,4,6-trichloropyrimidine, 2,4-, 6-tribromopyrimidine, 2,4-, 5,6-Ietrachloropyrimidine and 2,4,6-trichloro-5-cyanopyrimidine.

The azo compounds of formula III are detailed in the literature and can be prepared from diazotizable aromatic amines and coupling components in the usual manner getting produced.

Examples of aromatic amines which can be used in the preparation of the azo compounds of the formula III are: aniline, o-, m- or p-oluidine, o-, m- or p-chloroaniline, o-, m- or p-bromoaniline, o-, m- or p-oyanoaniline, o-, m- or p-anisidine, 4- or 5-chloro-2-anisidine, 4- or 5-chloro-2-toluidine, 2-trifluoromethylaniline , 2-trifluoromethyl-Λ-chloroaniline, aniline-2-, 3- or 4-sulfonic acid, aniline-2,5- or 3-4-disulfonic acid, 2-aminophenol- ^z 1- or 6-sulfonic acid, 4- or 5 -Sulfo-2-aminobenzoic acid, 4- (or 6-) chloro ^ -aminophenol-6-C or 4-) sulfonic acid, 2-aminophenol- ^, 6-disulfonic acid, ^ - (acetylamino or methyl or methoxy) aniline -2-sulfonic acid, i-naphthylamine-37, ² I-, 5- »6-, 7- or 8-sulfonic acid, 2-aminonaphthalene-i-, 5-» 6- »7- or 8-sulfonic acid, i -Naphthylamine-2,7-, 3,6-, 3,8-, 4,6- or 4,7-disulfonic acid, 1-naphthylamine-3,6,8- or 2,5,7-tert-isulfonic acid, 1-Amino-8-naphthol-4-sulfonic acid, 2-l-taphthylamine-1,5- »3,7-» 4,8-, 5 »7- or 6,8-disulfonic acid, 2- Naphthylamine-3,6,8-trisulfonic acid, 5-acetylaminoaniline-2-sulfonic acid, 2,5-dichloroaniline-4-sulfonic acid, aniline-5-sulfoanilide-2-sulfonic acid, 3-aminoacetanilide, 4-aminoacetanilide and 4-amino- 4 · - nitrostilbene-2,2 »-disulfonic acid.

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2A04358

Examples of coupling components used in the manufacture the azo compounds of the formula III can be used are Ν, Ν-dimethylaniline, Ν, Ν-diethyl-m-toluidine, m-toluidine, N, N-di (a-hydroxyethyl) -m-toluidine, N-methyl-N (ß-sulfatoethyl) aniline, i-naphthylamine-6- or 7- * sulphonic acid, 2-methoxy-1-naphthylamine-6-sulphonic acid, 2 ~ methylaminonaphthalene-7-sulfonic acid, 2-naphthylamine-6-, 7- or 8-sulfonic acid, 2-naphthylamine-3,7-, 4,8-, 5,7- or 6,8-disulfonic acid and the N-lower alkyl and N-aryl derivatives thereof, 2-naphthylamine-5- or 6-sulfonamide, 1-naphthylamine-7-sulfonmethylamide, 1-phenylaminonaphthalene, i-phenylaminonaphthalene-8-sulfonic acid and 1-ethylaminonaphthalene.

Suitable compounds of the formula IV are: 0-, m- and p-butylphenol, -Amylphenol and -hexylphenol; Cycloalkylphenols, such as, o- and p-cyclohexylphenol; Aralkylphenols, e.g. o-, m- and p-benzylphenol; Arylphenols such as o-, m- and p-phenylphenol; Alkoxyphenols such as hydroquinone and Eesorcinol monoalkyl ether, in which the alkyl radical can consist of ethyl, propyl, butyl, amyl, hexyl and heptyl; Cycloalkoxyphenols, such as p-cyclohexyloxyphenol; Aralkoxyphenols, such as p-benzyloxyphenol; Aryloxy phenols, e.g. p-phenoxyphenol; thio-substituted phenols, such as, o-, m- and p- (butylthio) phenol, o- and m- (hexylthio) phenol, o- (heptylthio) phenol, o- and p- (benzylthio) phenol, o-, mund.p- (phenylthio) phenol; Benzene thiols, such as p-butylbenzenethiol, p-butoxybenzenethiol, p- (butylthio) benzene thiol, p-amylbenzenethiol, p-hexylbenzenethiol, p-hexyloxybenzenethiol, p-biphenylenethiol and m- (phenylthio) benzenethiol.

Suitable compounds of the formula IV are, for example: arylamines, such as o- and p-butylaniline, p-cyclohexylaniline, 2,4-dimethylaniline, 4-butyl-2-methylaniline, ^ -Aminodiphenyl, ο- and p-Xthoxyaniline, p-Butoxyaniline,

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p-Cyclohexyloxyaniline, p-Phenoxyaniline, ο- and p-Ethylthioaniline, p-phenylthioaniline, 4-butyl-3-methoxyaniline, 4-butyl-2-bromoaniline; Alkylamines, such as 1-methyl-octylamine, octylamine, Dodecylamine, 3,3,5-trimethylcyclohexylamine, 4-butylcyclohexylamine, 4-butoxycyclohexylamine, 4-butylthiocyclohexylamine, and 2-octyloxyethylamine; Aralkylamines, e.g. 3-phenyl-1-methylethylamine, 3 ~ phenyl-1-methylpropylamine, 3-phenyl-i-butylpropylamine, ^ -Benzylcycloliexylamine, 2-phenoxyethylamine, 2- (4-butylphenoxy) ethylamine, 2-phenylthioethylamine and p-phenoxycyclohexylamine; aliphatic alcohols and Thiols, such as nonanol, dodecanol, 3,3 »5-trimethylcyclohexanol, p-butylcyclohexanol, 2-octyloxyethanol, p-butoxycyclohexanol, p-ethylthiocyclohexanol, 2-benzylcyclohexanol, 3-phenyl-i-methylpropanol, 2-phenoxyethanol, 2-phenylthioethanol, Nonanethiol and 2-phenoxyethanethiol.

Aromatic amines which contain a group of the formula V reactive with fibers can be prepared by that one condenses a compound of formula II with the corresponding diamine under such conditions that only one of the two amino groups reacts with the compound of formula II. Specific examples of such diamines are 1,3-phenylenediamine-4-sulfonic acid, 1,4-phenylenediamine-2-sulfonic acid, 1,3-phenylenediamine-4-, 6-disulfonic acid, 1,4-phenylenediamine-2,5-disulfonic acid and 2,6-diaminonaphthalene-4,8-disulfonic acid.

The reactions which lead to the formation of dyes of the formula I can be carried out using the compounds detailed in the literature on such reactions.

Polyamide textile materials made with the dyes of the formula I using conventional dyeing, padding or printing techniques can be colored are, for example, natural and

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synthetic polyamide textile materials such as wool, silk and nylon. The polyamides can be in any textile form such as in the form of threads, staple fibers, yarns, or woven or knitted goods.

The dyes are particularly useful for dyeing wool, including wool that is non-felting or machine washable has been made by chemical processes such as acid chlorination, application of hypochlorite under neutral or weakly alkaline conditions, use of permonosulfuric acid, use of the sodium salt of dichloroisocyanuric acid and deposition of polymers on the surface of the wool, for example amine / epichlorohydrin resins be used. Materials that have been treated in this way can be replaced by conventional Wool dyeing machines are treated, being in batches

Pad dyeing process or continuous pad / steaming process be used. When the dyes are applied to such fibers, they exhibit excellent fastness to wet treatments and to light.

The invention is illustrated in more detail by the following examples, in which all parts and percentages are expressed by weight are.

example 1

A solution of 12.5 parts of 2 - [/ J -'- (4 ", 6" -Dichlorotriazinylamino) -2 · -methyl] phenylazonaphthalene-4,8-disulfonic acid (45% concentration) in 200 parts of acetone and 200 parts water during 30 minutes to a solution of 1.75 parts of 4-tert-butylphenol in 100 parts of acetone at 5O ⁰ C was added, the pH of the reaction mixture by adding 10 sodium carbonate solution #iger 8.5 to 9 »0 is held . The reaction mixture is further under these conditions

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Stirred for 2 hours, the pH is adjusted to 7, and that. The product is filtered off with 5 # sodium chloride solution washed and dried

When the dye is from a neutral or weakly acidic Dyebath is applied to wool, then it gives a reddish yellow shade with excellent fastness to it wet treatments and against light.

The following table gives further examples of dyes which can be used according to the invention and which are prepared by diazotizing the aromatic amine given in the first column, coupling with the coupling component indicated in the second column, condensing with the acid chloride indicated in the third column or with the alkyloxy specified in the third column or alkylthiodichlorotriazinyl compound and subsequent condensation with the one in the fourth column given amine, phenol or thiol (if necessary).

When the dye is applied to wool or nylon, the shade given in the last column is obtained.

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at
game I. II III IV V 2 2-aminonaphthalenes, 8-
disulfonic acid 3-methylaniline Cyanuric chloride 4-hexylphenol reddish
yellow 3 It η η 4-cyclohexyl
phenol η 4th Aniline-3-sulfonic acid η η 4 - t-butyl-
phenol yellow 5 It η It 4-benzylphe-
nol H O
co 6th Aniline ^, 5-disulf on-
acid η It 4-butoxyphe-
nol It co 7th ti η η 4-butylaniline η ro 8th 4 — methoxyaniline-2-
sulfonic acid η Il 4-benzylthio-
phenol reddish
yellow 089 9 1-aminonaphthalene-5-
sulfonic acid It η 2-methyl-4-
butylaniline It 10 1-aminonaphthalene-6-
sulfonic acid η It 2-bromo-4—
butylaniline Il 11 1-aminonaphthalene-3,6-
disulfonic acid η η 2-heptyl
phenol η 12th 1 -Aminonaphthalin-4-, 7-
disulfonic acid η It Octylamine orange 13th 2-aminonaphthalene-1-
sulfonic acid η π ethylcyclo-
hexylamine reddish
yellow

at
game I. II III IV V 14th 2-aminonaplithalin-1,6-
disulfonic acid 3-ureidoaniline Cyanuric chloride 4-t-butylphe-
nol reddish
yellow 15th 2-aminonaphthalene-1,5-
disulfonic acid It 2- (2'-phenoxy-
ethoxy) -4,6-
dichloro-s-
triazine It η 16 2-naphthylamine-4,6,8-
trisulfonic acid 3-methylaniline 2,4,6-trichlo
ropyrimidine 4-hexylphenol It ■ ί-
Ο
co 17th 2,5-dichloroaniline-4-
sulfonic acid aniline Cyanuric chloride 4-t-butyl
phenol orange 832 / 18th Aniline-2,5-disulfone-
acid Il 2,4,5,6-tetra
chloropyrimi-
din 4-butylaniline reddish
yellow '1 0 8 9 19th ti η 2,4,6-trichlo
ro-5-cyano-
pyrimidine 4-t-butyl
phenol η 20th 4-amino-4'-nitrostilbene
2,2'-disulfonic acid It Cyanuric chloride η yellow 21 Il η η 4-hexylphenol It 22nd It 3-methylaniline η 4-t-amylphenol η 23 It Il η 4-butylaniline It 24 It ti 2-benzyloxy
4,6-dichloro-
s-triazine It

Example 25

An amino monoazo dye base is prepared by 5-acetylamino-2-aminobenzenesulfonic acid is diazotized, the diazotization product with N, N-di (β-hydroxyethyl) -m-toluidine ~ couples and hydrolyzes the acetylamino moiety in a dilute alkaline solution by standard methods.

A solution of 4.6 parts of this dye base (90 # concentration) in 2CX) parts of water is added at 0 to 5 ° C to a suspension of 2 parts of cyanuric chloride in 100 parts of water and 100 parts of acetone, the pH being adjusted by adding · 10 is held #iger sodium carbonate solution at 6 After one hour a solution of 1.8 parts of 4 ~ tert-butyl phenol · added in 100 parts of acetone, and the mixture for three hours at 3O ⁰ C and a pH of 8.5 to 9 »0 is stirred. The dye is precipitated at pH 7 by adding sodium chloride, washed with 5% sodium chloride solution and dried.

When applied to wool from a neutral or weakly acidic dye bath, the dye turns orange Shades with good fastness to light and with excellent fastness to wet treatments.

in the following table are further examples of dyes which can be used in accordance with the invention and, which are prepared by the method of Example 25 can, by diazotizing the in the first

⁷ .. aromatic

Column indicated / amines, domes with that in the second Coupling component indicated in the column, condensation with cyanuric chloride, and subsequent condensation with the in the amine, phenol or thiol indicated in the third column. But they can also be produced by the corresponding diamine given in the first column

■ 409832/1089

Cyanuric chloride condenses under such conditions that only one amino group reacts, whereupon the resulting dichlorotriazinylamino compound is obtained diazotized, the product obtained with the coupling component indicated in the second column couples and finally a condensation with the corresponding amine given in the third column, phenol or thiol. The shade that will be obtained when the dye is applied to wool or nylon is indicated in the fourth column.

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O CD OO CO

at
game I. II III IV 26th 4-acetylaminoaniline-
2-sulfonic acid N, N-Di (ß-hydroxy-
ethyl) aniline 4-ethoxyphenol orange 27 1,4 ~ phenylenediamine
2.5 ~ <3. isulfonic acid N-benzyl-N-ethylaniline 4 _T t-butylphenol η 28 Il N, N-diethylaniline 4-heptylphenol η 29 η N, N-diethyl-3-methyl-
aniline 4-butylthiophenol η 30th η It 4-butylaniline η 31 η η 4-t-butylphenol η 32 1,3-phenylenediamine
4,6-disulfonic acid 2-methylaminonaph-
thalin-7-sulfonic acid 4-hexylphenol reddish
yellow 33 It 2-aminonaphthalene
6-sulfonic acid 4-cyclohexyl
phenol η 34 ·. η ' N, N-Di (ß-hydroxyethyl) -
5-methylaniline 4-t-butylphenol orange

O • Ρ "» CO

Example 55

An amino disazo dye base is prepared by diazotizing 3-aminobenzenesulfonic acid, the diazotization product Couples with 1-naphthylamine 6- or? ~ sulfonic acid, the aminomonoazo compound is diazotized again and the product obtained is coupled with m-toluidine using standard procedures served.

The aminodisazo dye base thus prepared becomes sequential with cyanuric chloride and 4-hexylphenol by the process of Example 25 implemented. If the dye obtained comes from a neutral or weakly acidic dyebath Wool is applied, then brown shades with good fastness to light and with excellent Preserved fastness to wet treatments.

In the following table, further dye examples are given, which can be used according to the invention and which can be prepared by diazotizing the in the aromatic amine specified in the first column, coupling with the coupling component specified in the second column, renewed diazotization of the aminomonoazo compound obtained and coupling with the coupling component indicated in the third column. The aminodisazobase is then sequentially treated with cyanuric chloride and that indicated in the fourth column Amine, phenol or thiol condensed. The hue, obtained when the dye is applied to wool or nylon is given in the fifth column.

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at
game I. II III IV V 36 Aniline-2,5-disulfone-
acid 1-naphthylamine
6-sulfonic acid 3-methylaniline 4-hexylphenol Brown 37 Aniline-2-sulfonic acid It It 4-t-butyl
phenol π 38 4-chloroaniline ~ 2-
sulfonic acid Il η It η 39 It It 2-methyl-5-
methoxyaniline η η 0983 40 Aniline-3-sulfone
acid 1-naphthylamine
7-sulfonic acid N-methyl-N- (ß-
aminoethyl) -
aniline η bluish
Red 2/1 41 ti 2-methyl-5-
methoxyaniline η 4-butylaniline η ο
OO
co 42 Aniline-2,5-disulfone
acid ti η 4-t-butylphenol It 43 4-chloroaniline-2-
sulfonic acid 1-naphthylamine
7 "" sulfonic acid N-methyl-N- (ß-
aminoethyl) -1-
naphthylamine 4-butylthio
phenol bluish
violet 44 η It It 4-t-butyl
phenol Il 45 It. η . N-methyl-N- (ß-
aminoethyl) -
aniline 4-butylbenzene
thiol bluish
Red

-tr-CO

Example 46

An amino disazo dye base is made by diazotization of 4-acetylamino ^ -aminobenzenesulfonic acid, coupling with i-naphthylamine-6- or 7-sulfonic acid, renewed diazotization the aminomonoazo compound, coupling with N-phenyl-1-naphthylamine-8-sulfonic acid and hydrolyzing the acetylamino moiety in dilute alkaline solution, being everywhere Standard procedures are used.

A solution of 14.5 parts of the aminodisazo dye base obtained in this way (60% concentration) in 200 parts of water is added at 0 to 5 ° C. to a suspension of 2 parts of cyanuric chloride in 100 parts of water / water and 100 parts of acetone, the pH being is kept at 6 by adding 10 # sodium carbonate solution. After the mixture has been stirred for one hour under these conditions, it is added to a solution of 1.8 parts of 4-tert-butylphenol in 100 parts of acetone, whereupon the resulting mixture at 30 ^° C. and pH 8.5 to 9, 0 is stirred for two hours. The pH is then adjusted to 7 and the dye is precipitated with sodium chloride, washed with 5% sodium chloride solution and dried.

If the dye is applied to wool from a neutral or weakly acidic dye bath, then it becomes a navy blue Obtained hue with excellent fastness to light and wet treatments.

The following table gives further examples of dyes which are used according to the invention can and which can be prepared by adding the aromatic acetylamino compound indicated in the first column .diazotized, the product obtained with the coupling component indicated in the second column couples the

'"409832/1089

obtained aminomonoazo compound again diazotized and the obtained product with that given in the third column coupling component is coupling. The acetylaminodisazo compound is then hydrolyzed and sequentially with cyanuric chloride and the amine given in the fourth column, phenol or condensed thiol. The shade that is obtained when the dye is applied to wool or nylon, it is indicated in the fifth column.

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co

co ro

oo co

Bex-
game I. Il II III IV V 47 3-aminoacetaniidide 1-naphthylamine N-phenyl-1-naph- 4-t-butylphenol marine 5-acetylaminoani- 7-sulfonic acid thylamine-8-sul-
fonic acid blue 48 5-acetylamino 1in-2-sulfonic acid It ti It η anil in-2-sul fon η acid 49 4 ~ aminoacetanilide It It 4-t-amyl phenol η 50 η η It It 4-butylbenzene π thiol 51 4-acetylamino Λ -naphthylamine- dd 4-butylaniline η aniline-2-sulfone Il 6-sulfonic acid acid 52 It N-phenyl-1- 4-t-butylphenol It naphthylamine 53 1-naphthylamine N-ethyl-1- 4-hexylphenol dd 7-sulfonic acid naphthylamine It N- (4i-methoxy- 4-t-butylphenol η phenyl) -1- naphthylamine 55 2-methyl-5- N-ethyl-N-benz- 4-heptylphenol bluish methoxyaniline ylaniline-3'- Red sulfonic acid 56 It N, N -Di (ß-hydroxy 4-cyclohexyl η ethyl) aniline phenol

> S η *

j p

N) O OO

cn OO

Claims (1)

Claims 1. Process for dyeing polyamide textile materials, thereby characterized in that a polyamide textile material with an aqueous solution of an azo dye of the formula A-N = N-E NR ³ treated, wherein A represents the remainder of a diazo component of the benzene or naphthalene series with the exception of aniline-2,4-disulfonic acid or an alkylated or halogenated derivative thereof; E for the remainder. · Of a coupling component the aminobenzene or aminonaphthalene series, the aminonaphthalene being free from hydroxyl groups; X is = N-, «C-Cl or« C-CN; Y represents chlorine or bromine; Λ 4 4- Q is -0-, -S- or -NR -, where R is hydrogen or ρ
is lower alkyl; Q for a direct bond, —0—, —CO—, -SO ₀ -, -SO ₀ NH-, -NHSOo-. -CONH-, -NHCO-, -COO-, -OCO-, -0SO ₀ -, -S- or -NR ^ -, where R ^ is hydrogen or lower alkyl; R for an alkylene, cycloalkylene or arylene 2 is radical; R stands for an optionally substituted one Alkyl, cycloalkyl, aralkyl or aryl radical is such that R and R together do not have more than 13 carbon atoms contain; R is hydrogen or lower alkyl; where the group -NR- is attached to E, if not E represents the residue of a 1-naphthylamine-8-sulfonic acid or 409832/1089 is bonded to a terminal residue in A; and η is an integer from 1 to 3. 2. The method according to claim 1, characterized in that R ^{1 stands} for an arylene ^{radical and R 2} for an alkyl radical
with 4 to 7 carbon atoms. 5. The method according to claim 2, characterized in that 1 2 Q is oxygen and that Q is a direct bond stands. 4G9832 / 1089