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Патент USA US2111300

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Patented Mar. 15, 1938
2,1113%‘
UNITED. STATES PATENT OFFICE
2,111,300
MONOAZO-DYESTUFFS AND THEIR
MANUFACTURE
Emil Senn, Riehen, near Basel, Switzerland, as
signor to ?rm J. R. Geigy S. A., Basel, Switzer
land
No Drawing. Application January 14, 1937, Se
rial No. 120,617. In Great Britain February 10,
1936
20‘ Claims. (Cl. 260-96)
5
According to this invention valuable new violet
to green-blue monoazo-dyestuffs insoluble in
lacquers prepared with these substances or
they may be used, after they have been brought
water are made by combining a diazo-compound.
of a nitro-amino-sulphone of the general for
mula
into a ?ne state of subdivision by suitable addi
tions, for dyeing textiles, ?lms or shaped masses
according to the suspension method.
By means of the new dyestuffs it is possible to CR
produce violet to green-blue shades discharge
able to pure white, such as have hitherto been
obtained only with coupling components of the
aminonaphthalene and aminonaphthol series.
10
However‘, the dyestuffs prepared with these com
ponents are practically without application
in which
X represents hydrogen, a nitro group or halogen,
and
15
R represents an alkyl group such as methyl,
ethyl, butyl and so on, with a mono-asyl
meta-phenylenediamine of the following gen
eral formula
especially for dyeing acetyl-cellulose owing to
their exceedingly unsatisfactory fastness to light.
/
20
R1
N\ R:
IlTH—Ac
25
In the last named formula Ac represents a
substituted or unsubstituted acyl radical such
as HCO-—, CH3CO~—, C2H5CO—, C3H7CO-—-,
C11H23CO--, C2I-Li--OHCO——, R1 represents a
30 ‘group such as methyl, ethyl, propyl, butyl,
w-hydroxyethyl, B,»y-dihydroxypropy1, p-hydroxy
'y - chloropropyl,
B - hydroxy - 'y - alkoxypropyl,
epoXy-propyl, or a polyhydroxylalkyl radical of
the sugar series, a phenyl group and so on, and
35 ' R2 represents hydrogen or one of the groups
represented by R1, R1 and R2 being the same or
different in the case of tertiary substituted N~
atoms.
The azo component may contain any other de
sired substituents subject, of course, to the con
dition that such substituents do not destroy the
capacity for coupling and do not impart solu
bility in water to the dyestuffs.
The new dyestuffs have in general a very good
in alcohols, ketones, hydrocarbons
such as petroleum, paraf?n or benzine, oils, waxes
and in the various modern solvents and their
mixtures. It has‘ been found that it is possible
45 ‘ solubility
to adapt in large degree the solubility properties
50 to the various purposes of application by suitable
choice of the acid residue of the acylamino
group.
Some of‘ the new dyestuffs are distinguished by
a very good solubility in cellulose esters and cel~
lulose ethers. They may either be dissolved in.
The new coupling components used in the present
invention thus ?ll an important gap especially in
the construction of violet to blue acetyl cellulose
dyestuffs which are fast to light.
Hitherto‘ blue shades capable of being dis
charged and having good fastness properties
could be produced on acetate arti?cial silk only 20
with dyestu?s from 1-diazo~6-halogen-2,4-di
nitrobenzenes and a few selected coupling com
ponents of the benzene series, such as alkyl-w
hydroxyalkyl-cresidines. With these dyestuffs 25
there were obtained at the best reddish-blue
shades having the great disadvantage that they
suffered considerable change towards red under
arti?cial light. The production of blue dis
chargeable acetate arti?cial silk dyestuffs whose
pure blue shades are not altered in arti?cial
30
light but remain unchanged in tint and purity
is therefore an object much to be desired. These
requirements are ful?lled to a large extent, and
in some cases practically completely, by the dye
stuffs of the present invention. They include ‘
new dyestuffs which are distinguished by blue
shades which are considerably displaced towards
green and could not hitherto be obtained by
means of hitherto known aZo-components of the
benzene series.
The use of mono-acyl-meta-phenylenediamines
and their homologues and substitution products
capable of being coupled as azo-components for
making yellow to orange dyestuffs for dyeing cel 45
lulose esters and ethers has already been pro
posed in U. S. Patent No. 1,692,493. However,
all the dyestuffs of this patent contain a free
amino-group which can be diazotized and used
for the production of developing dyestuffs on the 50
?bre. From these dyestuffs the dyestu?s of the
present invention diifer in that they contain a
secondary or tertiary amino-group in para-posi»
tion to the azo-group. The acylamino group con
tained in the coupling components of the new
2
2,111,300
dyestuffs proves to be the substituent which
causes in most marked degree the hitherto known
displacement of the shade towards blue or green.
Consequently, the shades of all the new dyestuffs
having the acylamino-group in ortho-position to
the azo~group are displaced towards the blue end
of the spectrum to a greater extent than those
of the quite analogously constructed dyestuffs
completed by the addition of sodium acetate and
the dyestuff which has precipitated is isolated in
the usual manner and dried. It is a dark powder
which is soluble in acetone or ethyl-acetate to a
blue solution, and in the form of a suspension
dyes acetate arti?cial silk blue shades.
A similar dyestu? is obtained if the correspond
ing ethylsulphone is used.
containing other substituents such as alkyl or
The constitution of the
acid radical in the acylamino-group has itself
Example 4
10 alkoxy in said. position.
practically no eifect on the shade; this is of great
importance in the production of the new dye
stu?s which are to be adapted to various different
15 solvents and emulsifying agents, since the sol
ubility properties are dependent on the acyl
group and can be varied by variation of this
group without affecting the shade.
The following examples illustrate the inven—
tion, the parts being by weight.
Example 1
21.6 parts of 5-nitro-2-aminophenylmethyl
sulphone are diazotized in the usual manner with
25 the required proportion of nitrosylsulphuric acid.
When diazotization is ?nished the mixture is
poured into a large quantity of ice-water and
the diluted diazo solution is ?ltered if necessary.
The clear solution is allowed to run into an
aqueous solution of 28.2 parts of é-ethoxy-B-di
w-hydroxyethylamino-1-acetanilide. The forma
tion of the dyestuff can be accelerated by neu
tralization of the strongly acid reaction towards
Congo by addition of sodium acetate. After the
formation of the dyestuii is ?nished the insoluble
dyestuff which has precipitated is ?ltered and
washed until neutral. When dry it is a dark
powder which is soluble in organic solvents such
as alcohol, acetone or ethyl-acetate to blue solu
tions. In the form of a suspension it dyes acetate
40 arti?cial silk pure blue shades which can be dis
charged to white.
The azo-component used in this example can
be made by heating 4-ethoxy-3-amino-1-acet
anilide with a hydroxyethylating agent such as
45 glycol-chlorhydrin with addition of an acid
23.8 parts of 3-di-w-hydroxyethylamino-l-acet
anilide. When coupling is ?nished the dyestu? 15
is separated by ?ltering, washed until neutral
and dried. It is a dark powder which is soluble
in acetone or ethyl-acetate to a red-violet solu
tion, and in the form of a suspension dyes acetate
arti?cial silk violet shades which can be dis
charged to a pure white.
A similar dyestu? is obtained if the correspond
ing ethylsulphone is used.
3-di-w-hydroxyethylamino-l-acetanilide can be
made by the action of glycol-chlorhydrin on 3 25
amino~l-acetanilide in the presence of an acid~
binding agent. The base is very easily soluble in
water and in alcohol and crystallizes in the form
of colourless prisms of melting point 119° C.
30
Example 5
26.1 parts of 2-amlno-3,5-dinitro-l-phenyl
methylsulphone are diazotized in concentrated
sulphuric acid with a nitrosylsulphuric acid corre—
sponding with 6.9 parts of sodium nitrite. When
diazotization is ?nished the diazotization mixture
is ?ltered and allowed to run in a thin stream
into an ice-cold aqueous solution of 26.6 parts of
4-ethoxy-3 - (ethyl awhydroxyethyl) -amino-1-ac
etanilide while well stirring. When formation of 40
the dyestuif is completeed the whole is ?ltered
and the dyestuff washed until neutral and. dried.
The new dyestu? is a dark powder which is sol
uble in acetone or ethyl-acetate to a green-blue
solution. In the form of a suspension it dyes 45
acetate arti?cial silk fast green-blue shades
which have a particularly beautiful colour by
evening light and can be discharged to a pure
white.
small colourless needless of melting point 131° C
Example 2
sponding ethylsulphone is used.
sulphone are diazotized in the usual manner with
a nitrosylsulphuric acid corresponding with 6.9
parts of sodium nitrite, and the mixture is poured
on to ice and then coupled with an aqueous solu
tion of 28.2 parts of 4-methoxy-3-(ethyl-B,'y-di
hydroxypropyl)-amino-1-acetanilide.
The for
mation of the dyestuff is completed by the addi
tion of sodium acetate and the dyestuff is isolated
in the usual manner and dried. It is a dark
powder which dissolves in acetone or ethyl
acetate to a blue solution, and in the form of a
suspension yields blue shades on acetate arti?cial
silk.
A similar dyestuff is obtained by using as diazo
component the corresponding ethylsulphone.
Example 3
A diazo-compound prepared in the usual man
ner from 21.6 parts of 5-nitro-2-aminophenyl
methylsulphone is combined with an aqeuous
solution of 26.8 parts of 4-methoxy-3-di-w-hy—
75
from 21.6 parts of 5-nitro-2-aminophenylmethyl
sulphone is coupled with an aqueous solution of
binding agent such as calcium carbonate, mag
nesium carbonate or sodium carbonate. When
recrystallized from water the new base forms
21.6 parts of 5-nitro-2-aminophenylmethyl
60
1O
A diazo-solution prepared in the usual manner
droxyethyl-amino - l - acetanilide.
Coupling
is
A similar dyestuif is obtained if the corre
50
4-ethoxy-3- (ethyl — w - hydroxyethyl) -amino-1
acetanilide can be obtained by mono-hydroxy
ethylating 4 - ethoxy - 3 - amino-l-acetanilide in
known manner and ethylating directly by means 55
of diethyl-sulphate the intermediate product
without isolating it. The 4-ethoxy-3-(ethyl-w—
hydroxyethyl) ~amino-1-acetanilide is thus ob
tained in an aqueous solution which can be fur
ther used directly.
60
Example 6
26.1 parts of 2-amino-3.5-dinitro-1-phenyl
methylsulphone are diazotized in known manner
and the diazo-compound is coupled in an ice-cold 65
aqueous solution with 23.8 parts of 3-di-w-hy—
droxyethylamino ~ 1 - acetanilide.
The dyestuff
formed is isolated in the usual manner. When
dried it is a dark powder which is soluble in
acetone or ethyl-acetate to a blue-violet solution, 70
and in the form of a suspension dyes acetate arti
?cia-l silk fast blue-violet shades which can be
discharged to a pure white.
A dyestuff having similar properties is obtained
if the corresponding ethylsulphone is used.
76
3
2,111,300
Example 7
26.1 parts of 2-amino-3,5-dinitro—1-phenyl
methylsulphone are diazotized with nitrosylsul
phuric acid corresponding with 6.9- parts of so
dium nitrite and the diazo-compound is coupled
consisting of hydrogen, a nitro group and hal
ogen, and
R. represents a lower alkyl group, with a mono
acyl-meta-phenylenediamine of the following
general formula
with an ice-cold aqueous alcoholic solution of
—-N
28.2 parts of 4-ethoxy-3-di-w-hydroxyethylami
/
R1
\R2
no-l-acetanilide. By the addition of sodium ace
tate coupling is completed and the formed dye
10
10 stuff precipitated. When dried it is a dark pow
der which is soluble in acetone or ethyl-acetate
to a green-blue solution, and in the form of a
15
suspension dyes acetate arti?cial silk green-blue
.shades having a particularly beautiful evening
colour.
Dyestuifs of analogous properties. are obtained
if instead of the 2-amino~3,5-dinitro-l-phenyl
methyl- or -ethylsulphones or Examples 5-7 there
are employed the 2-amino-3-halogen-5-nitro-1
phenylalkylsulphones such as 2-amino-3-chloro
5-nitro-l-phenylmethyl- or ~ethylsulphone.
If instead of the methyl- or ethyl-sulphones
used in the foregoing examples there are used
sulphones having higher alkyl-groups such as
25
butyl and so on, similar dyestuffs are obtained
In the alkylated amino-group in the coupling
components there may be present instead of a
3,w-hydro$;yethyl, ethyl-?,'y-dihydroxypropyl or
30
NH-Ac
in which
Ac represents an acyl radical selected from the
group consisting of HCO—, CHsCO—-,
15
C2H5CO——, C3H7CO~—-, C11H23CO— and
C2H4OHCO,
R1 represents a monovalent organic radical and
R2 represents a radical selected from the group
consisting of hydrogen and monovalent organic
radicals, the other free positions of the azo
ents provided that they do not inhibit the cou
pling and impart solubility in water to the dye
stuffs.
2. A process for the manufacture of monoazo
NH:
these substituents may be used. In this manner
the shade and also in some cases the solubility
can be in?uenced. For making dyestuifs for ace
40
ent, for this group has a very favourable influence
on the a?inity for acetyl cellulose or the solu
bility in the cellulose ester derivative.
Instead of the acetyl-group in the acetyl-meta
phenylenediamine derivatives used in the above
examples, there may, of course, be present other
|
N02
in which
X represents a radical selected from the group
consisting of hydrogen, a nitro group and halo
gen, and
R represents a lower alkyl group,
40
with a mono-acyl-meta-phenylenediamine of the
following general formula
acyl-residues such as are indicated in the fore
/
going description. Formyl and lactyl derivatives
are in general suitable in the case of dyestuffs
for dyeing cellulose esters, whether in the form of
textiles, ?lms, masses or lacquers. Higher acyl
residues, such as lauryl and so on, are suitable
in the case of dyestuffs for colouring fats, oils,
waxes, turpentine, benzine and so on, whilst dye
stuffs from urea or urethane derivatives are
freely soluble in lower alcohols or similar organic
solvents or mixtures thereof.
The azo' component may contain other nuclear
substituents in the free positions, provided that
they do not inhibit the ‘coupling and impart solu
bility to the dyestuffs; particularly the position
4 of the 1,3-acyldiamines is favourable and from
the substituents the alkoxy groups like meth- and
ethoxy are the best suitable.
What I claim is:—
.
1. A process for the manufacture of monoazo
dyestuffs comprising combining a diazo-com
pound of a nitro-amino-sulphone of the general
formula
R1
R2
1lIH—Ac
in which
Ac represents an acyl radical selected from
the group consisting of HCO—,CI-I3CO-,
C2H5CO—, C3H7CO——, C11H23CO— and
R1 and R2 represent the same monovalent organic ,
radicals, the other free positions of the azo~
component containing also nuclear substitu
ents provided that they do not inhibit the cou
pling and impart solubility in water to the dye
stuffs.
3. A process for the manufacture of monoazo
dyi‘estuffs comprising combining a diazo-com
pound of a nitro-amino-sulphone of the general
formula
lTTHz
’
‘ 1TH:
X-
-SO2R
111.0‘;
in which
N02
in which
X represents a radical selected from the group
25
dyestuffs comprising combining a diazo-com
pound of a nitro-amino-sulphone of the general
formula
ethyl~w—hydroxyethyl-group, any of the groups
indicated in the general description or, although
only once, hydrogen; all possible combinations of
tate arti?cial silk it is to be recommended that
at least one hydroxyalkyl-group should be pres
20
component containing also nuclear substitu~
X represents a radical selected from the group
consisting of hydrogen, a nitro group and halo
gen, and
R represents a lower alkyl group,
GO
4
2,111,300
with a mono-acyl-meta~phenylenediamine of the
consisting of hydrogen, a nitro group and halo
following general formula
gen, and
R1
_N/
\R,
‘
R represents a lower alkyl group,
with a mono-acyl-meta-phenylenediamine of the
following general formula
3
/ l
N
\R,
IlIH—Ac
NH~—Ac
10 in which
Ac represents an acyl radical selected from
the group consisting of HCO-—, CH3CO—,
C2H5CO—, C3H7CO-—, C11H23CO— and
C2H4OHCO——, and
15 R1 and R2 represent different monovalent organic
radicals, the other free positions of the azo
component containing also nuclear substitu
10
in which
Ac represents an acyl radical selected from
the group consisting of HCO—, CH3CO-,
15
C2H5CO—, C3H7CO—~, C11H23CO— and
ents provided that they do not inhibit the cou
R1 and R2 represent di?erent radicals selected
pling and impart solubility in water to the dye
stuffs.
pyl, butyl, w-hydroxyethyl, BN-dihydroxypro
pyl, B-hydroxy-y-chloropropyl, ?-hydroXy-v
alkoxypropyl, epoxypropyl, polyhydroxy alkyl
4. A process for the manufacture of monoazo
dyestuffs comprising combining a diazo-com
pound of a nitro-amino-sulphone of the general
formula
25
from the group consisting of methyl, ethyl, pro
20
radicals of the sugar series, a phenyl group, the
other free positions of the azo-component con
taining also nuclear substituents provided that
they do not inhibit the coupling and impart 25
solubility in water to the dyestuffs.
6. A process for the manufacture of monoazo
dyestuffs comprising combining diazotized 5-ni
tro-2-aminophenylmethylsulphone with 4-meth
30
|
N02
in which
X represents a radical selected from the group
consisting of hydrogen, a nitro group and halo
gen, and
R represents a lower alkyl group,
with a monoacyl~1neta-phenylenediamine of the
following general formula
oxy - 3 - (ethyl -p,'y-dihydroxypropyl) — amino-l
30
acetanilide.
'7. A process for the manufacture of monoazo
dyestuffs comprising combining diazotized 5-ni
tro-2-aminophenylmethylsulphone with 4-meth
oxy-3-di-w-hydroxyethylamino-l-acetanilide.
35
8. A process for the manufacture of monoazo
dyestuffs comprising combining diazotized 2-am
ino-3,5-dinitro-l-phenylmethylsulphone with 3
di-w-hydroxyethylamino-l-acetanilide.
4-0
9. As new products, the azo-dyestu?s of the 40
general formula
NH-Ac
45 in which
Ac represents an acyl radical selected from
the group consisting of HCO--, CH3CO—,
C2H5CO—, C3H7CO—, C11H23CO— and
R1 represents a radical selected from the group
consisting of methyl, ethyl, propyl, butyl, w
hydroxyethyl, ,8,'y-dihydroxypropyl, B-hy
droxy-y-chloropropyl, p-hydroxy-y-alkoxypro
pyl, epoxypropyl, polyhydroxyalkyl radicals of
the sugar series, a phenyl group,
R2 represents a radical selected from the group
consisting of hydrogen and the said group from
which R1 is selected, the other free positions of
the azo-component containing also nuclear
substituents provided that they do not inhibit
the coupling and impart solubility in water to
the dyestuffs.
in which
X represents a radical selected from the group
consisting of hydrogen, a nitro group and halo
gen,
R represents a lower alkyl group,
Ac represents an acyl radical selected from
the group consisting of HCO——-, CH3CO—-,
Ca C1
C2H5CO—, C3I-I7CO—, C11I-I23CO— and
R1 represents a monovalent organic radical, and
R2 represents a radical selected from the group
consisting of hydrogen and monovalent organic
radicals, the three free positions in the acyl 60
diamino-nucleus being occupied by any other
substituent, said dyestuffs being insoluble in
5. A process for the manufacture of monoazo
water and dyeing alcohols, ketones, hydrocar
dyestuffs comprising combining a dia-zo-com
pound of a nitro-amino-sulphone of the gener
bons and cellulose derivatives violet to green
a1 formula
17TH:
blue shades, the dyeings on ?bres being dis
chargeable to white.
10. As new products, the azo-dyestuffs of the
general formula
70
X
N
/
l
NO1—
/
R1
\RI
N=N—
N0:
in Which
X represents a radical selected from the group
s 02R
in which
rim-Ac
75
5
2,111,300
X represents a radical selected from the group
consisting of hydrogen, a nitro group and halo
gen,
13. As new products, the azo-dyestuffs of the
general formula
,
R represents a lower alkyl group,
,
Ac represents an acyl radical selected from the
R1 and R2 represent the same monovalent organic
radicals, the three free positions in the acyl-di
amino-nucleus being occupied by any other
substituent, said dyestuffs being insoluble in
water and dyeing alcohols, ketones, hydrocar
bons and cellulose derivatives violet to green
blue shades, the dyeings on ?bres being dis
15
chargeable to white.
11. As new products, the azo-dyestuffs of the
general formula
10
R1
20
/"
NOPQN=N
s 03R
25
N<
NH-Ac
R2
in which
X represents a radical selected from the group
consisting of hydrogen, a nitro group and halo
gen,
30 R represents a lower alkyl group,
Ac represents an acyl radical selected from
the group consisting of HCO—, CH3CO—,
C2H5CO—-, C3H7CO—‘-, C11H23CO—- and
in which
X represents a radical selected from the group
consisting of hydrogen, a nitro group and halo~
10
gen,
R represents a lower alkyl group,
Ac represents an acyl radical selected from 15
the group consisting of I-ICO—-, CHsCO—,
C2H5CO—, C3H7CO—, C11H23CO— and
R1 and R2 each represent the same radicals se
lected from the group consisting of methyl, 20
ethyl, propyl, butyl, w-hydroxyethyl, pq-dihy
droxypropyl, ,6-hydroxy-'y-chloropropyl, ,c-hy
droxy-y-alkoxypropyl, epoxypropyl, polyhy
droxyalkyl radicals of the sugar series, a phenyl
group, the three free positions in the acyl-di 25
amino-nucleus being occupied by any other
substituent, said dyestu?s being insoluble in
water and dyeing alcohols, ketones, hydrocar
bons and cellulose derivatives violet to green
blue shades, the dyeings on ?bres being dis 30
chargeable to white.
14. As new products, the azo-dyestuffs of the
general formula
35 R1 and R2 represent different monovalent organ
ic radicals, the three free positions in the acyl
diamino-nucleus being occupied by any other
35
substituent, said dyestuffs being insoluble in
water and dyeing alcohols, ketones, hydrocar
:40
bons and celulose derivatives violet to green
blue shades, the dyeings on ?bres being dis
chargeable to white.
12. As new products, the alto-dyestuffs of the
general formula
801B1
in which
X represents a radical selected from the group
consisting of hydrogen, a nitro group and halo
gen’
'
R represents a lower alkyl group,
45
Ac represents an acyl radical selected from
the group consisting of I-ICO-—, CH3CO———,
C2H5CO—, CsI-I'zCO——-, C11H23CO—- and
R1 and R2 represent different radicals selected
from the group consisting of methyl, ethyl, 50
50
X represents a radical selected from the group
consisting of hydrogen, a nitro group and halo
55
gen,
R represents a lower alkyl group,
Ac represents an acyl radical selected from
the group consisting of HCO-—, CH3CO—,
C2H5CO—, CsI-I'zCO-——, C11H2sCO-—- and
60
R1 represents a radical selected from the group
consisting of methyl, ethyl, propyl, butyl, w-hy
droxyethyl, [3,v-dihydroxypropyl, e-hydroxy-v
65
chloropropyl, ,Ei-hydroxy-y-alkompropyl, epox
ypropyl, polyhydroxyalkyl radicals of the sugar
propyl, butyl, w-hydroxyethyl, j8,'y-dihydroxy
propyl, ?-hydroxy-v-chloropropyl, p-hydroxy
y-alkoxypropyl, epoxypropyl, polyhydroxyal
kyl radicals of the sugar series, a phenyl group, 55
the three free positions in the acyl-diamino
nucleus being occupied by any other substi
tuent, said dyestuffs being insoluble in water
and dyeing alcohols, ketones, hydrocarbons and
cellulose derivatives violet to green-blue shades, 60
the dyeings on ?bres being dischargeable to
white.
15. As new products, the ago-dyestuffs of the
formula
Y
65
series, a phenyl group,
R2 represents a radical selected from the group
consisting of hydrogen and the said group from
which R1 is selected, the three free positions in
70
75
the acyl-diamino-nucleus being occupied by
any other substituent, said dyestuffs being in
soluble in water and dyeing alcohols, ketones,
hydrocarbons and cellulose derivatives violet
to green-blue shades, the dyeings on ?bres be
ing dischargeable to white.
70
in which
X represents a radical selected from the group
consisting of hydrogen and a nitro group,
R represents a lower alkyl group,
75
6
2,111,300
R1 and R2 represent radicals selected from the
group of lower alkyl and hydroxyalkyl radicals,
Y represents any substituent not imparting solu
bility in water, said dyestu?s being insoluble
in water and dyeing alcohols, ketones, hydro
carbons and cellulose derivatives violet to green
blue shades, the dyeings on ?bres being dis
chargeable to white.
16. As new products, the azodyestuifs of the
10 formula
Y represents a member of the group consisting of
H, methoxy and ethoxy.
18. As new products, the azo-dyestuffs of the
formula
OCH:
|
02H:
N
NO:
CHzOHCHzOH
N=N
I
802R
OH
10
NH—C O CH:
in which R is selected from the group consisting
of methyl and ethyl, being dark powders insoluble
in water, soluble in acetone and in ethyl-acetate
to blue solutions and dyeing acetate silk blue 15
shades, the dyeings being dischargeable to White.
19. As new products the azo-dyestuffs of the
formula
in which
20
R1 and R2 represent radicals selected from the
group of lower alkyl and hydroxyalkyl radicals,
Y represents a member of the group consisting of
25
hydrogen and —O—(1ower alkyl), said dye
stuffs being insoluble in water and dyeing alco
hols, ketones, hydrocarbons and cellulose de
rivatives violet to green-blue shades, the dye
30
ings on ?bres being dischargeable to white.
17. As new products, the azo-dyestuffs of the
formula
Y
35
OCH:
X represents a radical selected from the group
consisting of hydrogen and a nitro group,
R represents a lower alkyl group,
X
I
1
NOa-
._N\ CH2CH2OH
N=N
S 02R
CHzCHaOH
I
NH—C 0 CH3
25
in which R is selected from the group consisting
of methyl and ethyl, being dark powders insolu
ble in water and soluble in acetone and in ethyl
acetate to blue solutions and dyeing acetate silk
blue shades, the dyeings being dischargeable to 30
white.
20. As new products the azo-dyestu?s of the
formula
——-N/
I
S 0 2R
R
I
\
35
R:
NH~C O CE:
40 in which
X represents a radical selected from the group
consisting of hydrogen and a nitro group,
R represents a lower alkyl radical selected from
the group of methyl and ethyl,
,. R1 and R2 represent same or di?erent radicals se
lected from the group of methyl, ethyl, w-hY
droxyethyl, ppy-dihydroxypropyl,
in which R is selected from the group consisting
of methyl and ethyl, being dark powders insolu
ble in water and soluble in acetone and in ethyl
acetate to blue-violet solutions and dyeing ace
tate silk blue-violet shades, the dyeings being dis
chargeable to white.
EMIL SENN.
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