The invention relates to compounds of the general formula (I): 
##STR2## 
in which B.sup.1 to B.sup.5 are each hydrogen or C.sub.1 to C.sub.4 alkyl; 
R.sup.1 is hydrogen, alkyl or hydroxy; 
R.sup.2, R.sup.3, R.sup.5, R.sup.6 and R.sup.7 independently of one another 
are hydrogen, chloro, bromo, fluoro, methyl, ethyl, methoxy or ethoxy; 
R.sup.4 is hydrogen, alkyl, benzyl, phenylethyl, phenyl or phenyl bearing 
chloro, bromo, methyl, ethyl, methoxy, ethoxy, cyano, dialkylamino or 
SO.sub.3 H as a substituent; 
X is --O--, --S--, --NR.sup.8 --, --NR.sup.8 CO--, --NR.sup.8 SO.sub.2 --, 
--OSO.sub.3 -- or --SO.sub.3 --; 
R.sup.8 is hydrogen, alkyl or alkyl bearing hydroxy or C.sub.1 to C.sub.4 
alkoxy as a substituent; 
A is hydrogen, sodium, potassium, ammonium, substituted ammonium or 
unsubstituted or substituted alkyl, cycloalkyl, aralkyl or aryl; and 
--NR.sup.8 -- and A together are an optionally quaterized saturated or 
unsaturated heterocyclic ring. Examples of dialkylaminophenyl radicals 
R.sup.4 are C.sub.1 to C.sub.4 dialkylaminophenyl such as 
dimethylaminophenyl, diethylaminophenyl or dibutylaminophenyl. 
Examples of alkyl radicals R.sup.1, R.sup.4 and R.sup.8 are those of one to 
six carbon atoms such as hexyl, amyl, butyl or propyl and particularly 
methyl or ethyl. Radicals R.sup.8 may also be .beta.-hydroxyethyl, 
.beta.-methoxyethyl, .beta.-ethoxyethyl, .beta.-propoxyethyl, 
.beta.-butoxyethyl, .beta.-methoxypropyl, .beta.-ethoxypropyl, 
.beta.-propoxypropyl or .beta.-butoxypropyl. Examples of alkyl radicals 
B.sup.1 to B.sup.5 are butyl, propyl, ethyl and methyl. B.sup.1 to B.sup.5 
are preferably hydrogen or methyl. Radicals A may be hydrogen or for 
example C.sub.1 to C.sub.13 alkyl which may be interrupted by oxygen or 
sulfur and may bear, as a substituent, hydroxy, C.sub.1 to C.sub.4 alkoxy, 
phenoxy, cyano, chloro, bromo, carboxy, carbomethoxy, carboethoxy, 
carbobutoxy, carbamoyl, N-alkylcarbamoyl (alkyl being C.sub.1 to C.sub.6), 
SO.sub.3 H, amino, C.sub.1 to C.sub.8 alkylamino or dialkylamino, 
pyrrolidino, piperidino, hexamethyleneamino, morpholino, piperazino, 
N-methylpiperazino, N-.beta.-hydroxyethylpiperazino, quaternary ammonium 
or cyclic ammonium. 
The following specific radicals A are given by way of example: 
CH.sub.3, C.sub.2 H.sub.5, C.sub.3 H.sub.7, C.sub.4 H.sub.9, C.sub.5 
H.sub.11, C.sub.6 H.sub.13, C.sub.7 H.sub.15, C.sub.8 H.sub.17, C.sub.9 
H.sub.19, C.sub.10 H.sub.21 C.sub.13 H.sub.27, C.sub.2 H.sub.4 OH, C.sub.3 
H.sub.6 OH, 
##STR3## 
C.sub.4 H.sub.8 OH, C.sub.6 H.sub.12 OH, C.sub.2 H.sub.4 OC.sub.2 H.sub.4 
OH, C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OH, C.sub.2 H.sub.4 OCH.sub.3, 
C.sub.3 H.sub.6 OCH.sub.3, C.sub.4 H.sub.8 OCH.sub.3, C.sub.6 H.sub.12 
OCH.sub.3, C.sub.2 H.sub.4 OC.sub.2 H.sub.5, C.sub.3 H.sub.6 OC.sub.2 
H.sub.5, C.sub.4 H.sub.8 OC.sub.2 H.sub.5, C.sub.2 H.sub.4 OC.sub.3 
H.sub.7, C.sub.3 H.sub.6 OC.sub.3 H.sub.7, C.sub.2 H.sub.4 OC.sub.4 
H.sub.9, C.sub.3 H.sub.6 OC.sub.4 H.sub.9, C.sub.3 H.sub.6 OC.sub.8 
H.sub.17, C.sub.2 H.sub.4 OC.sub.6 H.sub.5, C.sub.3 H.sub.6 OC.sub.6 
H.sub.5, C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3, C.sub.2 H.sub.4 
OC.sub.2 H.sub.4 OC.sub.2 H.sub.5, C.sub.2 H.sub.4 OC.sub.2 H.sub.4 
OC.sub.4 H.sub.9, C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OC.sub.6 H.sub.5, 
C.sub.2 H.sub.4 (OC.sub.2 H.sub.4).sub.2 OCH.sub.3, C.sub.2 H.sub.4 
(OC.sub.2 H.sub.4).sub.2 OC.sub.2 H.sub.5, C.sub.2 H.sub.4 SCH.sub.3, 
C.sub.2 H.sub.4 SC.sub.2 H.sub.5, C.sub.2 H.sub.4 SC.sub.4 H.sub.9, 
C.sub.2 H.sub.4 S-CH.sub.2 -C.sub.6 H.sub.5, C.sub.2 H.sub.4 CN, C.sub.5 
H.sub.10 CN, C.sub.6 H.sub.12 CN, C.sub.7 H.sub.14 CN, C.sub.2 H.sub.4 
OC.sub.2 H.sub.4 CN, C.sub.2 H.sub.4 OC.sub.2 H.sub.4 CN, C.sub.3 H.sub.6 
OC.sub.2 H.sub.4 CN, C.sub.2 H.sub.4 Cl, C.sub.3 H.sub.6 Cl, C.sub.4 
H.sub.8 Cl, C.sub.6 H.sub.12 Cl, C.sub.2 H.sub.4 Br, C.sub.3 H.sub.6 Br, 
C.sub.2 H.sub.4 SO.sub.3 H, CH.sub.2 COOH, CH.sub.2 -COOCH.sub.3, C.sub.2 
H.sub.4 COOH, C.sub.2 H.sub.4 COOC.sub.2 H.sub.5, C.sub.2 H.sub.4 
COOC.sub.4 H.sub.9, C.sub.2 H.sub.4 CONHC.sub.4 H.sub.9, C.sub.2 H.sub.4 
CONHCH.sub.3, C.sub.2 H.sub.4 CONHC.sub.2 H.sub. 5, C.sub.2 H.sub.4 
CONHC.sub.6 H.sub.13, 
##STR4## 
C.sub.2 H.sub.4 NH.sub.2, C.sub.2 H.sub.4 NH-CH.sub.3, C.sub.3 H.sub.6 
NHC.sub.2 H.sub.5, C.sub.3 H.sub.6 NHC.sub.3 H.sub.7, C.sub.2 H.sub.4 
NHC.sub.4 H.sub.9, 
##STR5## 
C.sub.3 H.sub.6 NHC.sub.6 H.sub.13, C.sub.3 H.sub.6 NHC.sub.8 H.sub.17, 
C.sub.2 H.sub.4 N(CH.sub.3).sub.2, C.sub.2 H.sub.4 N(C.sub.2 
H.sub.5).sub.2, C.sub.2 H.sub.4 N(C.sub.3 H.sub.7).sub.2, C.sub.2 H.sub.4 
N(C.sub.4 H.sub.9).sub.2, C.sub.2 H.sub.4 N(C.sub.5 H.sub.11).sub.2, 
C.sub.2 H.sub.4 N(C.sub.6 H.sub.13).sub.2, 
##STR6## 
C.sub.3 H.sub.6 N(CH.sub.3).sub.2, C.sub.3 H.sub.6 N(C.sub.2 
H.sub.5).sub.2, C.sub.3 H.sub.6 N(C.sub.3 H.sub.7).sub.2, C.sub.3 H.sub.6 
N(C.sub.4 H.sub.9).sub.2, 
##STR7## 
C.sub.4 H.sub.8 N(CH.sub.3).sub.2, C.sub.4 H.sub.8 N(C.sub.2 
H.sub.5).sub.2, C.sub.4 H.sub.8 N(C.sub.4 H.sub.9).sub.2, C.sub.4 H.sub.8 
N(C.sub.5 H.sub.11).sub.2, C.sub.4 H.sub.8 N(C.sub.6 H.sub.13), 
##STR8## 
C.sub.6 H.sub.12 N(CH.sub.3).sub.2, C.sub.6 H.sub.12 N(C.sub.2 H 
.sub.5).sub.2, C.sub.6 H.sub.12 N(C.sub.4 H.sub.9).sub.2, C.sub.6 H.sub.12 
N(C.sub.6 H.sub.13).sub.2, 
##STR9## 
Cycloalkyl, aralkyl or aryl radicals A are for example: 
##STR10## 
CH.sub.2 C.sub.6 H.sub.5, C.sub.2 H.sub.4 C.sub.6 H.sub.5, C.sub.2 H.sub.4 
C.sub.6 H.sub.4 SO.sub.3 H, 
##STR11## 
C.sub.2 H.sub.4 C.sub.6 H.sub.4 CH.sub.3, C.sub.2 H.sub.4 C.sub.6 H.sub.4 
CH.sub.3, 
##STR12## 
C.sub.6 H.sub.4 CH.sub.3, C.sub.6 H.sub.3 (CH.sub.3).sub.2, C.sub.6 
H.sub.4 OCH.sub.3, C.sub.6 H.sub.4 OC.sub.2 H.sub.5, C.sub.6 H.sub.4 OH, 
##STR13## 
C.sub.6 H.sub.4 OC.sub.2 H.sub.4 OH, C.sub.6 H.sub.4 Cl, C.sub.6 H.sub.3 
Cl.sub.2, C.sub.6 H.sub.4 Br, C.sub.6 H.sub.4 SO.sub.3 H, C.sub.6 H.sub.3 
(SO.sub.3 H).sub.2 Examples of radicals 
##STR14## 
are: 
##STR15## 
Compounds of the formula (I) may be prepared by reacting a compound of the 
general formula (II): 
##STR16## 
with a compound of the general formula (III): 
EQU H-X-A (III) 
in the presence of a base, X being --O--, --S--, --NR.sup.8 --, --NR.sup.8 
CO--, --SO.sub.3 -- or --NR.sup.8 SO.sub.2 --. 
Compounds of the formula (II) may be obtained by reacting a compound of the 
general formula (IV) or (V): 
##STR17## 
B being Cl, Br or dialkylamino, with a compound of the general formula 
(VI): 
##STR18## 
Compounds of the formula (VI) are accessible in the following way: 
##STR19## 
Compounds of the formula (VI) 
Compounds of the formula (I) in which X-A is OSO.sub.3 H may be obtained 
for example by reacting a compound of the general formula (I) in which X-A 
is OH with sulfuric acid. 
Compounds of the formula (I) in which XA is SO.sub.3 Na may be obtained 
from compounds of the formula (I) in which XA is OSO.sub.3 Na or from (II) 
with an alkali metal sulfite, for example sodium sulfite. 
Compounds of the formula (I) may also be prepared by the following method 
(B.sup.1 to B.sup.5 being shown as hydrogen for the sake of simplicity): 
##STR20## 
Compounds of the general formula (I). 
Compounds of the formula (I) may also be obtained by reacting a compound of 
the general formula (VIa): 
##STR21## 
with a compound of the general formula (IV) or (V). 
Compounds of the general formula (VIa) are accessible by the following 
method: 
##STR22## 
Compounds (I) in which R.sup.1 is OH may be obtained from a compound of the 
general formula (VII): 
##STR23## 
with a compound of the formula (III). 
Compounds of the formula (VII) may be obtained by reacting a compound of 
the formula (VIII): 
##STR24## 
with a compound of the formula (IV) or (V). 
Compounds of the formula (VIII) are accessible as follows: 
##STR25## 
Compounds of the formula (I) in which R.sup.1 is OH may also be obtained by 
reacting a compound of the formula (IX): 
##STR26## 
with a compound of the formula (IV) or (V). 
Compounds of the general formula (IX) may be obtained as follows: 
##STR27## 
Compounds of the formula (I) in which R.sup.1 is OH may furthermore be 
obtained by the reaction of a compound of the formula (with B.sup.1 to 
B.sup.5 represented as hydrogen for the sake of simplicity): 
##STR28## 
or a precursor thereof of the formula: 
##STR29## 
with a compound of the formula (III): H-X-A (III). 
Details concerning the reactions will be found in the Examples in which 
parts and percentages are by weight unless otherwise stated. 
Particular industrial importance attaches to compounds of the general 
formula (Ia): 
##STR30## 
in which R.sup.1 is hydrogen or hydroxyl and XA has the meanings given 
above. 
X is preferably --O--, --NR.sup.8 -- or --SO.sub.3 -- and A is preferably 
hydrogen, sodium, potassium, C.sub.1 to C.sub.8 alkyl, an amino group 
bearing one or two C.sub.1 to C.sub.4 alkyl as substituents, alkyl bearing 
the said heterocyclic rings as substituents and radicals containing 
quaternary nitrogen. 
Preferred radicals 
##STR31## 
are: 
##STR32## 
The following formula (Ia) covers compounds that are within the scope of 
the invention: 
##STR33## 
in which B.sup.3 is hydrogen or C.sub.1 to C.sub.4 alkyl, 
R.sup.2, R.sup.3, R.sup.5, R.sup.6 and R.sup.7 are independently hydrogen, 
chlorine, bromine, fluorine, methyl, ethyl, methoxy or ethoxy, 
R.sup.4 is hydrogen, C.sub.1 to C.sub.4 alkyl, benzyl, phenylethyl, phenyl 
or phenyl substituted by chlorine, bromine, methyl, ethyl, methoxy, 
ethoxy, cyano or hydroxysulfonyl, 
R.sup.8 is hydrogen, C.sub.1 - to C.sub.4 -alkyl or C.sub.2 or C.sub.3 
-alkyl substituted by hydroxy or C.sub.1 - to C.sub.4 -alkoxy and 
A is C.sub.2 or C.sub.3 alkyl substituted by C.sub.1 to C.sub.4 
dialkylamino, piperidino, pyrrolidino or hexamethyleneimino. 
Compounds of the formula (Ia) wherein R.sup.2, R.sup.3, R.sup.4, R.sup.5 
and R.sup.6 are hydrogen; compounds of the formula (Ia) wherein B.sup.3 is 
hydrogen; compounds of the formula (Ia) wherein R.sup.7 is chlorine; and 
compounds of the formula (Ia) wherein A is C.sub.2 or C.sub.3 alkyl 
substituted by C.sub.1 to C.sub.4 dialkylamino are also within the scope 
of the invention. 
The compounds of the general formula (I) are suitable as optical 
brighteners for cellulose esters and particularly for acrylonitrile 
polymers, wool and polyamides. Brilliant white effects are obtained having 
good fastness properties and particularly high degrees of whiteness. The 
compounds of the formula (I) are moreover suitable for use in detergents 
for brightening paper. The main method of application is liquor dyeing. 
The production of precursors 
EXAMPLE A 
(a) 80 parts of p-acetylaminobenzenesulfinic acid is dissolved with 44 
parts of sodium bicarbonate in 400 parts of water. 76 parts of 
epichlorohydrin is dripped in at 45.degree. to 50.degree. C. and the whole 
is stirred for another two hours at 45.degree. to 50.degree. C. It is then 
allowed to cool, the pH of the solution is adjusted to 11.5 by adding 30 
parts of 50% by weight caustic soda solution, and 85 parts (83.5% of 
theory) of 4-acetylaminophenyl-3'-hydroxypropene-2'-sulfone having a 
melting point of 165.degree. to 170.degree. C. is isolated by suction 
filtration. The molecular weight (calculated and found) is 255. NMR 
(D-DMSO): 
2.1(S), 4.2(M), 5.2(T), 6.65(brD), 6.95(brD), 7.8(S), 10.3(brS), 
3:2:1:1:1:4:1. 
(b) 63.7 parts of 4-acetylamino-3'-hydroxypropene-2'-sulfone is heated for 
an hour at 100.degree. C. in a mixture of 90 parts of water and 90 parts 
of concentrated hydrochloric acid. After the whole has been cooled to 
0.degree. to 5.degree. C. diazotization is carried out with a solution of 
17.3 parts of sodium nitrite in 50 parts of water. The diazonium solution 
is dripped into a solution of 188 parts of sodium sulfite in 550 parts of 
water, stirred for one hour at ambient temperature, 100 parts of 
concentrated sulfuric acid is added, and the whole is heated for four 
hours at 100.degree. C. After cooling the pH is adjusted to 10. The 
product is suction filtered and 41 parts (71.9% of theory) of 
4-hydrazinophenyl-3'-hydroxypropene-2'-sulfone having a melting point of 
136.degree. to 142.degree. C. is isolated. 
(c) 11.4 parts of 4-hydrazinophenyl-3'-hydroxypropene-2'-sulfone and 10.15 
parts of 4-chloro-.beta.-chloropropiophenone are boiled under reflux in 50 
parts of methyl glycol for two hours. The whole is cooled and 14 parts 
(74.5% of theory) of the compound of the formula: 
##STR34## 
having a melting point of 224.degree. to 228.degree. C. is isolated by 
suction filtration. The compound has a pale yellow color (.alpha..sub.max. 
(dimethylformamide): 367 mm) and exhibits a blue fluorescence in solution. 
The following compounds are prepared by the method described in Example A: 
______________________________________ 
##STR35## 
A.sub.1 
H H H H 3-Cl Cl 222-229 
greenish 
blue 
A.sub.2 
H H H 5-Cl 2-CH.sub.3 
Cl 245-250 
greenish 
blue 
A.sub.3 
H H CH.sub.3 
H H Cl 218-226 
blue 
A.sub.4 
2-Cl 5-Cl H H H Cl 256-264 
blue 
______________________________________ 
EXAMPLE B 
(a) 305 parts of p-acetylaminobenzenesulfinic acid is dissolved with 300 
parts of sodium acetate in 1200 parts of water. 168 parts of 
epichlorohydrin is dripped in within two hours at 40.degree. to 45.degree. 
C. and the whole is stirred for another two hours at 40.degree. to 
45.degree. C. The whole is allowed to cool and is suction filtered. The 
yield is 265 parts of 
4-acetylaminophenyl-2'-hydroxy-3'-chloropropylsulfone having a melting 
point of 174.degree. to 176.degree. C. NMR (D-DMSO): 
2.1(S), 3.45(D), 3.60(D), 4.1(M), 5.2(D), 7.82(S), 10.4(brS), 3:2:2:1:1:4:1 
(b) 58.4 parts of the compound from (a) is heated for one hour at 
100.degree. C. in 80 parts of water and 80 parts of concentrated 
hydrochloric acid. The whole is cooled and diazotized at 0.degree. to 
5.degree. C. with a solution of 14.5 parts of sodium nitrite in 30 parts 
of water. Thirty minutes later the reaction mixture is poured into a 
solution of 150 parts of sodium sulfite in 250 parts of water and stirred 
for one hour at 10.degree. to 15.degree. C. After 70 parts of sulfuric 
acid has been added the whole is stirred for another hour at ambient 
temperature. The pH of the solution is then adjusted to 4.5 by dripping in 
50% caustic soda solution; an oil thus separates and slowly crystallizes. 
The yield is 52 parts of 
4-hydrazinophenyl-2'-hydroxy-3'-chloropropylsulfone having a melting point 
of 96.degree. to 98.degree. C. (after recrystallization from a mixture of 
ethyl acetate and cyclohexane). 
(c) 66 parts of the compound from (b) and 51 parts of 
4-chloro-.beta.-chloropropiophenone are heated in 500 parts of ethyl 
alcohol for forty-five minutes at 75.degree. to 78.degree. C. The whole is 
then cooled and 75 parts of the compound of the formula: 
##STR36## 
is isolated. It has a melting point of 157.degree. to 158.degree. C. 
The following compounds are prepared by the method described in Example B: 
__________________________________________________________________________ 
##STR37## 
Fluorescence in 
Ex. 
R.sub.4 
R.sub.5 
R.sub.6 
R.sub.7 
B.sub.1 
B.sub.2 
B.sub.3 
B.sub.4 
B.sub.5 
dimethylformamide 
__________________________________________________________________________ 
B.sub.1 
H H 3-Cl 
Cl 
H H H H H greenish blue 
B.sub.2 
H 5-Cl 
2-CH.sub.3 
Cl 
H H H H H greenish blue 
B.sub.3 
H H H Cl 
CH.sub.3 
H H H H blue 
B.sub.4 
H H H Cl 
H H H CH.sub.3 
H blue 
B.sub.5 
H H H Cl 
H H CH.sub.3 
H H blue 
B.sub.6 
H H H Cl 
H H H CH.sub.3 
CH.sub.3 
blue 
__________________________________________________________________________ 
EXAMPLE C 
20.6 parts of the compound from Example B(c), 5 parts of sodium acetate and 
5 parts of sodium iodide are heated in 300 parts of methyl ethyl ketone 
for ten hours at 60.degree. to 65.degree. C. The whole is cooled to 
ambient temperature and 400 parts of water and 400 parts of petroleum 
ether are added. 18 parts of the compound: 
##STR38## 
having the melting point 154.degree. to 156.degree. C. (after 
recrystallization from toluene) is isolated by suction filtration. 
The natural color of the compound is pale yellow; a solution of the 
compound in dimethylformamide has an intensely blue fluorescence. 
The following compounds are prepared by the method described in Example C: 
______________________________________ 
##STR39## 
Fluorescence in 
Ex. R.sup.4 R.sup.5 R.sup.6 
R.sup.7 
dimethylformamide 
______________________________________ 
C.sub.1 
H H 3-Cl Cl greenish blue 
C.sub.2 
H 5-Cl 2-CH.sub.3 
Cl greenish blue 
C.sub.3 
CH.sub.3 
H 3-Cl Cl greenish blue 
______________________________________ 
EXAMPLE D 
20.6 parts of the compound from Example B(c) and 10 parts of sodium acetate 
are heated in 30 parts of acetic anhydride for two hours at 100.degree. C. 
The whole is allowed to cool and the product is hydrolyzed with 700 parts 
of water and suction filtered. 18 parts of the compound: 
##STR40## 
is isolated; it has a melting point of 179.degree. to 182.degree. C. The 
compound is pale yellow in color; its solution in dimethylformamide has a 
greenish blue fluorescence.