Novel stilbene compounds of the formula ##STR1## in which A is the radical ##STR2## in which R.sub.1 is hydrogen or chlorine and R.sub.2 is hydrogen or alkyl, Z is hydrogen, chlorine or phenyl and R.sub.3 is hydrogen, alkyl or chlorine, as well as their use in a process for optically brightening organic material are described.

The present application relates to novel stilbene compounds and a process 
for their preparation and to processes for the optical brightening of 
organic materials by means of these novel stilbene compounds. 
The stilbene compounds according to the invention are of the formula 
##STR3## 
in which A is the radical 
##STR4## 
in which R.sub.1 is hydrogen or chlorine and R.sub.2 is hydrogen or alkyl 
having 1 to 4 C atoms, Z is hydrogen, chlorine or phenyl and R.sub.3 is 
hydrogen, alkyl having 1 to 4 C atoms, or chlorine. 
The preferred alkyl radical in R.sub.2 and R.sub.3 is the methyl radical. 
Within the scope of the formula (1), compounds of interest are, in 
particular, those of the formulae 
##STR5## 
in which R.sub.1 is hydrogen or chlorine, R.sub.2 is hydrogen or alkyl 
having 1 to 4 C atoms and Z is hydrogen, chlorine or phenyl. 
Preferred compounds are the stilbene compounds of the formulae 
##STR6## 
in which Z is hydrogen, chlorine or phenyl, and also those of the formula 
##STR7## 
in which R'.sub.2 is hydrogen or methyl and Z is hydrogen, chlorine or 
phenyl. 
The stilbene compounds according to the invention can be prepared by 
various processes. Thus, the compounds of the formula (1) can be prepared 
by reacting a Schiff's base of the formula 
##STR8## 
in which k is hydrogen or chlorine and Z and R.sub.3 are as defined above, 
with a methyl compound of the formula 
##STR9## 
in which A is as defined above, in dimethylformamide and in the presence 
of a strongly basic alkali metal compound. 
Compounds used as the strongly basic alkali metal compound are, depending 
on the reactivity of the Schiff's base (anil) employed, alkali metal 
compounds of the formula 
EQU YOC.sub.m-1 H.sub.2m-1 ( 10) 
in which m is an integer from 1 to 6 and preferably 2 to 6 and Y is an 
alkali metal ion, preferably sodium or potassium, for example potassium 
hydroxide or, especially, potassium tertiary butylate. In the case of 
alkali metal alcoholates, the reaction must be carried out in a virtually 
anhydrous medium, whilst in the case of potassium hydroxide a low water 
content of up to about 15% (for example content of water of 
crystallisation) is still permissible. 
The compounds containing methyl groups are reacted with the anils in 
equivalent amounts, i.e. in a molar ratio of 1:1, so that no component is 
present in a substantial excess. Advantageously, at least the equivalent 
amount of the alkali metal compound is used, i.e. at least 1 mol of a 
compound containing, for example, a KO group per mol of aldehyde-anil. 
When potassium hydroxide is used, preferably the 4-fold to 8-fold amount 
is employed. 
The reaction is carried out at temperatures in the range between about 
10.degree. and 50.degree. C. and, if necessary in order to initiate the 
reaction, with irradiation with additional UV light having a wavelength of 
more than 300 mm. The use of low temperatures is advantageous if the 
reactants contain ring compounds or substituents which can easily be 
opened or, respectively, detached, or otherwise chemically changed by 
alkali. This applies, for example, in the case of anils having easily 
detachable chlorine substituents. The preparation of the anil and the 
reaction thereof with the tolyl compound can also be carried out in a 
one-pot process. For example, the aldehyde is heated with excess aniline 
in dimethylformamide, the reaction mixture is avaporated completely in 
vacuo, the tolyl component and dimethylformamide are added and the 
customary procedure is followed. The end products can be worked up from 
the reaction mixture by conventional methods which are known per se, for 
example by precipitating them with water. 
The starting materials of the formulae (8) and (9) are known or are 
prepared analogously to processes which are known per se. 
The compounds of the formulae (2) to (6) are prepared in an analogous 
manner by reacting Schiff's bases of the formulae indicated below with 
methyl compounds of the formulae indicated below: 
__________________________________________________________________________ 
For com- 
pounds 
of the 
formula 
Schiff's base Methyl compound 
__________________________________________________________________________ 
(2) 
##STR10## 
##STR11## 
(3) 
##STR12## 
##STR13## 
(4) 
##STR14## 
##STR15## 
(5) 
##STR16## 
##STR17## 
(6) 
##STR18## 
##STR19## 
(7) 
##STR20## 
##STR21## 
__________________________________________________________________________ 
In the formulae (8) and (11) to (16), k, R.sub.1, R'.sub.2 and Z are as 
defined above. 
The methyl compounds of the formulae (11), (12), (14) and (16) can be 
prepared, for example, in accordance with the following equations: 
EQUATION 1 
Preparation of 3-(3-chloro-4-methyl-phenyl)-6-chloro-1,2-benzisoxazole 
##STR22## 
EQUATION 2 
Preparation of 2-(3-chloro-4-methylphenyl)-s-triazolo[1,5-a]pyridine 
##STR23## 
The compounds of the formula (1) can also be prepared by reacting one mol 
equivalent of a compound of the formula 
##STR24## 
with one mol equivalent of a compound of the formula 
##STR25## 
in the presence of a strong base and of a solvent, A, R.sub.3 and Z being 
as defined above and one of the symbols Q.sub.1 and Q.sub.2 being a --CHO 
group and the other being one of the groupings of the formulae 
##STR26## 
in which R is an unsubstituted or substituted alkyl, aryl, cycloalkyl or 
aralkyl radical. 
The starting materials of the formulae (17) and (18) are known or can be 
prepared analogously to processes which are known per se. 
The novel compounds defined above exhibit a more or less pronounced 
fluorescence in the dissolved or finely dispersed state. They can be used 
for optically brightening the most diverse synthetic, semi-synthetic or 
natural organic materials or substances which contain such organic 
materials. The novel compounds have good to very good fastness to light. 
The following groups of organic materials, where optical brightening 
thereof is relevant, may be mentioned as examples of the above, without 
the survey given below being intended to express any restriction thereto: 
I. Synthetic Organic High-molecular Materials 
(a) Polymersiation products based on organic compounds containing at least 
one polymerisable carbon-carbon double bond, i.e. their homopolymers or 
copolymers as well as their after-treatment products, for example 
crosslinking, grafting or degradation products, polymer blends or products 
obtained by modification of reactive groups, for example polymers based on 
.alpha.,.beta.-unsaturated carboxylic acids or derivatives of such 
carboxylic acids, especially on acrylic compounds (for example acrylates, 
acrylic acid, acrylonitrile, acrylamides and their derivatives or their 
methacrylic analogues), on olefine hydrocarbons (for example ethylene, 
propylene, styrenes or dienes and also so-called ABS polymers), and 
polymers based on vinyl and vinylidene compounds (for example vinyl 
chloride, vinyl alcohol and vinylidene chloride), 
(b) Polymerisation products which are obtainable by ring opening, for 
example polyamides of the polycaprolactam type, and also polymers which 
are obtainable either via polyaddition or via polycondensation, such as 
polyethers or polyacetals, 
(c) Polycondensation products or precondensates based on bifunctional or 
polyfunctional compounds possessing groups capable of undergoing 
condensation reactions, their homo-condensation and co-condensation 
products, and after-treatment products, for example polyesters, especially 
polyesters which are saturated (for example ethylene glycol terephthalic 
acid polyesters) or unsaturated (for example maleic acid/dialcohol 
polycondensates as well as their crosslinking products with 
copolymerisable vinyl monomers), unbranched or branched polyesters (also 
including those based on polyhydric alcohols, for example alkyd resins), 
polyamides (for example hexamethylenediamine adipate), maleate resins, 
melamine resins, their precondensates and analogues, polycarbonates and 
silicones, and 
(d) Polyaddition products such as polyurethanes (crosslinked and 
non-crosslinked) and epoxide resins. 
II. Semi-synthetic Organic Materials, for example cellulose esters of 
varying degrees of esterification (so-called 21/2-acetate or triacetate) 
or cellulose ethers, regenerated cellulose (viscose or cuprammonium 
cellulose) or their aftertreatment products, and casein plastics. 
III. Natural organic materials of animal or vegetable origin, for example 
based on cellulose or proteins, such as cotton, wool, linen, silk, natural 
lacquer resins, starch and casein. 
The organic materials to be optically brightened can be in the most diverse 
states of processing (raw materials, semi-finished goods or finished 
goods). On the other hand, they can be in the form of structures of the 
most diverse shapes, i.e., for example, in the form of predominantly 
three-dimensional bodies, such as slabs, profiles, injection mouldings, 
various machined articles, chips, granules or foams, and also in the form 
of predominantly two-dimensional bodies, such as films, sheets, lacquers, 
coverings, impregnations and coatings, or in the form of predominantly 
one-dimensional bodies, such as filaments, fibres, flocks and wires. The 
said materials can, on the other hand, also be in unshaped states, in the 
most diverse homogeneous or inhomogeneous forms of division, for example 
in the form of powders, solutions, emulsions, dispersions, latices, pastes 
or waxes. 
Fibre materials can, for example, be in the form of continuous filaments 
(stretched or unstretched), staple fibres, flocks, hanks, textile 
filaments, yarns, threads, fibre fleeces, felts, waddings or flocked 
structures or in the form of woven textile fabrics or textile laminates or 
knitted fabrics and also in the form of papers, cardboards or paper pulps. 
The compounds to be used according to the invention are of importance, 
inter alia, for the treatment of organic textile materials, especially 
woven textile fabrics. Where fibres, which can be in the form of staple 
fibres or continuous filaments or in the form of hanks, woven fabrics, 
knitted fabrics, non-wovens, flocked substrates or laminates, are to be 
optically brightened according to the invention, this is advantageously 
effected in an aqueous medium in which the compounds in question are 
present in a finely divided form (suspensions, so-called micro-dispersions 
or possibly solutions). If desired, dispersing agents, stabilisers, 
wetting agents and further auxiliaries can be added during the treatment. 
Depending on the type of brightener compound used, it can prove 
advantageous to carry out the treatment in a neutral or alkaline or acid 
bath. The treatment is usually carried out at temperatures of about 
20.degree. to 140.degree. C., for example at the boiling point of the bath 
or near it (about 90.degree. C.). Solutions or emulsions in organic 
solvents can also be used for the finishing, according to the invention, 
of textile substrates, as is practised in the dyeing trade in so-called 
solvent dyeing (pad-thermofix application, or exhaustion dyeing processes 
in dyeing machines). 
The novel optical brighteners according to the present invention can 
further be added to, or incorporated in, the materials before or during 
shaping. Thus they can, for example, be added to the compression moulding 
composition or injection moulding composition during the production of 
films, sheets (for example, hot milling into polyvinyl chloride) or 
mouldings. 
Where fully synthetic or semi-synthetic organic materials are being shaped 
by spinning processes or via spinning compositions, the optical 
brighteners can be applied in accordance with the following processes: 
Addition to the starting substances (for example monomers) or intermediates 
(for example precondensates or prepolymers), i.e. before or during the 
polymersiation, polycondensation or polyaddition, 
powdering on to polymer chips or granules for spinning compositions, 
bath dyeing of polymer chips or granules for spinning compositions, 
metered addition to spinning melts or spinning solutions, and 
application to the tow before stretching. 
The novel optical brighteners according to the present invention can, for 
example, also be employed in the following use forms: 
(a) Mixed with dyestuffs (shading) or pigments (coloured pigments or 
especially, for example, white pigments), or as an additive to dye baths, 
printing pastes, discharge pastes or reserve pastes, and also for the 
after-treatment of dyeings, prints or discharge prints, 
(b) Mixed with so-called "carriers", wetting agents, plasticisers, swelling 
agents, anti-oxidants, light stabilisers, heat stabilisers and chemical 
bleaching agents (chlorite bleach or bleaching bath additive), 
(c) Mixed with crosslinking agents or finishing agents (for example starch 
or synthetic finishes), and in combination with the most diverse textile 
finishing processes, especially synthetic resin finishes (for example 
creaseproof finishes such as "wash-and-wear", "permanent-press" or 
"no-iron"), as well as flameproof finishes, soft handle finishes, 
anti-soiling finishes or anti-static finishes, or anti-microbial finishes, 
(d) Incorporation of the optical brighteners into polymeric carriers 
(polymerisation, polycondensation or polyaddition products), in a 
dissolved or dispersed form, for use, for example, in coating agents, 
impregnating agents or binders (solutions, dispersions and emulsions) for 
textiles, fleeces, paper and leather, 
(e) As additives to so-called "master batches", 
(f) As additives to the most diverse industrial products in order to render 
these more marketable (for example improving the appearance of soaps, 
washing agents and pigments), 
(g) In combination with other optically brightening substances, 
(h) In spinning bath formulations, i.e. as additives to spinning baths, 
such as are used for improving the slip for the further processing of 
synthetic fibres, or from a special bath before stretching the fibre, 
(i) As scintillators for various purposes of a photographic nature, for 
example for electrophotographic reproduction or supersensitisation, and 
(j) Depending on the substitution, as laser dyes. 
If the brightening process is combined with textile treatment methods or 
finishing methods, the combined treatment can in many cases advantageously 
be carried out with the aid of appropriate stable formulations which 
contain the optically brightening compounds in such concentration that the 
desired brightening effect is achieved. 
In certain cases, the brighteners are made fully effective by an 
after-treatment. This can be, for example, a chemical treatment (for 
example acid treatment), a thermal treatment (for example heat) or a 
combined chemical/thermal treatment. Thus for example, the appropriate 
procedure to follow in optically brightening a range of fibre substrates, 
for example polyester fibres, with the brighteners according to the 
invention, is to impregnate these fibres with the aqueous dispersions (or 
possibly also solutions) of the brighteners at temperatures below 
75.degree. C., for example at room temperature, and to subject them to a 
dry heat treatment at temperatures above 100.degree. C., it being 
generally advisable additionally to dry the fibre material beforehand at a 
moderately elevated temperature, for example at not less than 60.degree. 
C. and up to about 130.degree. C. The heat treatment in the dry state is 
then advantageously carried out at temperatures between 120.degree. and 
225.degree. C., for example by heating in a drying chamber, by ironing 
within the specified temperature range or by treatment with dry, 
superheated steam. The drying and dry heat treatment can also be carried 
out in immediate succession or can be combined in a single process stage. 
The amount of the novel optical brighteners to be used according to the 
invention, relative to the material to be optically brightened, can vary 
within wide limits. A distinct and durable effect is already achievable 
with very small amounts, in certain cases, for example, amounts of 0.0001 
percent by weight. However, amounts of up to about 0.8 percent by weight 
and in some cases of up to about 2 percent by weight can also be employed. 
For most practical purposes, amounts between 0.0005 and 0.5 percent by 
weight are of preferred interest. 
For various reasons it is frequently appropriate to employ the brighteners 
not as such, i.e. in the pure form, but as a mixture with very diverse 
auxiliaries and diluents, for example anhydrous sodium sulphate, sodium 
sulphate decahydrate, sodium chloride, sodium carbonate, alkali metal 
phosphates, such as sodium orthophosphate or potassium orthophosphate, 
sodium pyrophosphate or potassium pyrophosphate and sodium 
tripolyphosphates or potassium tripolyphosphates, or alkali metal 
silicates. 
The novel optical brighteners are also especially suitable for use as 
additives for wash liquors or industrial and domestic washing agents, to 
which they can be added in various ways. They are appropriately added to 
wash liquors in the form of their solutions in water or organic solvents 
or in a finely divided form, as aqueous dispersions. They are 
advantageously added to domestic or industrial washing agents in any stage 
of the manufacturing process of the washing agents, for example to the 
so-called "slurry" before spray-drying, to the washing powder, or to the 
preparation of liquid washing agent combinations. They can be added either 
in the form of a solution or dispersion in water or other solvents, or, 
without auxiliaries, as a dry brightener powder. For example, the 
brighteners can be mixed, kneaded or ground with the detergent substances 
and, in this form, admixed to the finished washing powder. However, they 
can also be sprayed in a dissolved or pre-dispersed form on to the 
finished washing agent. 
Possible washing agents are the known mixtures of detergent substances, for 
example soap in the form of chips and powders, synthetics, soluble salts 
of sulphonic acid half esters of higher fatty alcohols, arylsulphonic 
acids with higher and/or multiple alkyl substituents, sulphocarboxylic 
acid esters of medium to higher alcohols, fatty acid acylaminoalkyl- or 
acylaminoaryl-glycerolsulphonates, phosphoric acid esters of fatty 
alcohols and the like. Possible so-called "builders" which can be used 
are, for example, alkali metal polyphosphates and polymetaphosphates, 
alkali metal pyrophosphates, alkali metal salts of carboxymethylcellulose 
and other "soil redeposition inhibitors", and also alkali metal silicates, 
alkali metal carbonates, alkali metal borates, alkali metal perborates, 
nitrilotriacetic acid, ethylenediaminetetraacetic acid, and foam 
stabilisers, such as alkanolamides of higher fatty acids. The washing 
agent can further contain, for example: anti-static agents, superfatting 
skin protection agents, such as lanolin, enzymes, anti-microbial agents, 
perfumes and dyes. 
The novel optical brighteners have the particular advantage that they are 
also effective in the presence of active chlorine donors, for example 
hypochlorite, and can be used without significant loss of the effect in 
wash liquors containing non-ionic washing agents, for example alkylphenol 
polyglycol ethers. 
The compounds according to the invention are added in amounts of 0.005-1% 
or more, relative to the weight of the liquid or pulverulent, finished 
washing agent. Wash liquors which contain the indicated amounts of the 
optical brighteners claimed impart a brilliant appearance in daylight when 
used to wash textiles of cellulose fibres, polyamide fibres, cellulose 
fibres with a high quality finish, polyester fibres, wool and the like. 
The washing treatment is carried out, for example, as follows: 
The textiles quoted are treated for 1 to 30 minutes at 20.degree. to 
100.degree. C. in a wash liquor which contains 1 to 10 g/kg of a composite 
washing agent containing a builder and 0.05 to 1%, relative to the weight 
of washing agent, of the brighteners claimed. The liquor ratio can 1:3 to 
1:50. After washing, rinsing and drying are carried out as usual. The wash 
liquor can contain 0.2 g/l of active chlorine (for example as 
hypochlorite) or 0.1 to 2 g/l of sodium perborate, as a bleaching 
additive. 
In the examples, parts, unless otherwise indicated, are always parts by 
weight and percentages are always percentages by weight. Unless otherwise 
noted, melting points and boiling points are uncorrected.

EXAMPLE 1 
2.78 g of 3-(3-chloro-4-methylphenyl)-6-chloro-1,2-benzisoxazole of the 
formula 
##STR27## 
3.93 g of the Schiff's base obtained from 
2-(p-formylphenyl)-4-phenyl-5-chloro-2H-1,2,3-triazole and 
p-chloroaniline, of the formula and 2.5 g of potassium hydroxide powder 
having a water content of about 10% are stirred in 80 ml of 
dimethylformamide for one hour at 20.degree. to 30.degree. C. under 
nitrogen. After adding 360 ml of methanol, the mixture is cooled to 
-10.degree. C. and the product which has precipitated is filtered off with 
suction, washed with 50 ml of methanol and dried. This gives 4.68 g (86.0% 
of theory) of 
2-chloro-4-(6-chloro-1,2-benzisoxazol-3-yl)-4'-(4-phenyl-5-chloro-2H-1,2,3 
-triazol-2-yl)-stilbene of the formula 
##STR28## 
in the form of small yellow matted needles with a melting point of 
235.degree. to 236.degree. C. After recrystallising twice from toluene, 
with the aid of bleaching earth, 4.08 g (75% of theory) of small, 
greenish-tinged yellow, fine matted needles are obtained which melt at 
238.degree. to 239.degree. C. 
C.sub.29 H.sub.17 Cl.sub.3 N.sub.4 O (543.84) calculated: C 64.05, H 3.15, 
N 10.30%; found: C 64.26, H 3.37, N 10.15%. 
The compounds of the formula 
##STR29## 
listed in Table I which follows can be prepared in a similar manner: 
TABLE I 
______________________________________ 
No. R Melting point: .degree.C. 
______________________________________ 
(105) H 247-248 
(106) C.sub.6 H.sub.5 
240-241 
______________________________________ 
EXAMPLE 2 
2.78 g of 3-(3-chloro-4-methylphenyl)-6-chloro-1,2-benzisoxazole of the 
formula (101) and 3.59 g of the Schiff's base obtained from 
2-phenyl-4-(p-formylphenyl)-2H-1,2,3-triazole and o-chloroaniline, of the 
formula 
##STR30## 
are reacted in accordance with the instructions of Example 1. This gives 
4.72 g (92.7% of theory) of 
2-chloro-4-(6-chloro-1,2-benzisoxazol-3-yl)-4'-(2-phenyl-2H-1,2,3-triazol- 
4-yl)-stilbene of the formula 
##STR31## 
in the form of small, pale yellow needles with a melting point of 
211.degree. to 212.degree. C. After recrystallising twice from toluene 
with the aid of bleaching earth, 4.17 g (81.9% of theory) of small, 
bright, greenish-tinged yellow, matted needles are obtained which melt at 
211.degree. to 212.degree. C. 
C.sub.29 H.sub.18 Cl.sub.2 N.sub.4 O (509.40) calculated: C 68.38, H 3.56, 
N 11.00%; found: C 68.15, H 3.54, N 11.07%. 
The compounds of the formula 
##STR32## 
listed in Table II which follows can be prepared in an analogous manner: 
TABLE II 
______________________________________ 
No. Z Melting point: .degree. C. 
______________________________________ 
(204) Cl 220-221 
(205) C.sub.6 H.sub.5 
208-209 
______________________________________ 
EXAMPLE 3 
2.44 g of 2-(3-chloro-4-methylphenyl)-s-triazolo[1,5-a]pyridine of the 
formula 
##STR33## 
3.59 g of the Schiff's base obtained from 
2-phenyl-4-(p-formylphenyl)-2H-1,2,3-triazole and o-chloroaniline, of the 
formula (201), and 2.5 g of potassium hydroxide powder having a water 
content of about 10% are stirred in 80 ml of dimethylformamide for one 
hour at 20.degree. to 30.degree. C. under nitrogen. During the first 10 
minutes the reaction mixture is irradiated with ultraviolet light having 
wavelengths greater than 300 nm, and during this period the colour changes 
from pale yellow to violet. The reaction mixture is worked up analogously 
to Example 1 and 4.5 g (94.9% of theory) of 
2-chloro-4-[s-triazolo[1,5-a]pyrid-2-yl]-4'-(2-phenyl-2H-1,2,3-triazol-4-y 
l)-stilbene of the formula 
##STR34## 
are obtained in the form of small, pale yellow, matted needles with a 
melting point of 260.degree. to 261.degree. C. After recrystallisation 
from o-dichlorobenzene with the aid of bleaching earth and then from 
dimethylformamide, 3.7 g (78.1% of theory) of small pale, greenish-tinged 
yellow needles are obtained which melt at 264.degree. to 265.degree. C. 
C.sub.28 H.sub.19 ClN.sub.6 (474.96) calculated: C 70.81, H 4.03, N 17.69%; 
found: C 70.53, H 4.30, N 17.81%. 
The compounds of the formula 
##STR35## 
listed in Table III can be prepared in an analogous manner: 
TABLE III 
______________________________________ 
No. R.sub.2 Z Melting point: .degree. C. 
______________________________________ 
(304) CH.sub.3 H 242-243 
(305) H Cl 236-237 
(306) H C.sub.6 H.sub.5 
226-227 
______________________________________ 
EXAMPLE 4 
2.44 g of 2-(3-chloro-4-methylphenyl)-s-triazolo[1,5-a]pyridine of the 
formula (301) and 3.59 g of the Schiff's base obtained from 
2-(p-formylphenyl)-4-phenyl-2H-1,2,3-triazole and o-chloroaniline, of the 
formula 
##STR36## 
are reacted in accordance with the instructions of Example 3. This gives 
4.2 g (88.6% of theory) of 
2-chloro-4-[s-triazolo[1,5-a]pyrid-2-yl]-4'-phenyl-2H-1,2,3-triazol 
-2-yl]-stilbene of the formula 
##STR37## 
in the form of a pale yellow powder with a melting point of 281.degree. to 
282.degree. C. After recrystallisation from o-dichlorobenzene with the aid 
of bleaching earth, and then from xylene, 3.6 g (79.5% of theory) of 
small, bright greenish-tinged yellow, matted needles are obtained which 
melt at 291.degree. to 292.degree. C. 
C.sub.28 H.sub.19 ClN.sub.6 (474.96) calculated: C 70.81 H 4.03 N 17.69% 
found: C 70.50 H 4.26 N 17.64% 
The compounds of the formula 
##STR38## 
listed in Table IV can be prepared in an analogous manner. 
TABLE IV 
______________________________________ 
No. R.sub.2 Z Melting point: .degree. C. 
______________________________________ 
(404) CH.sub.3 H 226-227 
(405) H Cl 290-291 
(406) H C.sub.6 H.sub.5 
266-267 
______________________________________ 
EXAMPLE 5 
A polyester fabric (for example "Dacron") is padded at room temperature 
(about 20.degree. C.) with an aqueous dispersion which contains, per 
liter, 2 g of one of the compounds of the formulae (103), (202), (204), 
(205), (302), (304) to (306), (402) or (404) to (406) and 1 g of an 
addition product of about 8 mols of ethylene oxide and 1 mol of 
p-tert.-octylphenol and is dried at about 100.degree. C. The dry material 
is then subjected to a heat treatment at 170.degree. to 220.degree. C. and 
this treatment takes from 2 minutes to several seconds, depending on the 
temperature. The material treated in this way has a considerably whiter 
appearance than the untreated material.