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Патент USA US2134453

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2,134,453
Patented Oct. 25, 1938
v UNITED: STATES
PATENT OFFICE
2,134,453
MORDANT AZO-DYE’STUFVFS AND A PROCESS
FOR MAKING SAME
' ‘Max Miiller and Roger Ratti, Basel, Switzerland,
\
assignors to the ?rm Durand & Huguenin S. A.,
" Basel, Switzerland
~No Drawing. Application April 12, 1937, Serial
No. 136,510. In Germany April 20, 1936
24 Claims._ (01. 260-151)
’ This invention relates to the manufacture of
valuable mordant ortho-hydroxyazo-dyestu?sby
combining a diazo‘ compound‘ of an ortho-amino
H phenol or a substitution product thereof with 'a
5 '- l:B-aminonaphtholsulphonic ‘acid in which the
amino group is substituted by aradical —SO2-aryl-‘
' ortho-hydroxycarboxylic acid, especially a; con-‘
densation product of a salicylic acidsulphochlo
chromium mordants, for example according to
the processes of British Speci?cations Nos.
26460/1912 and 319457, U. S. Patent No. 1,848,589,
and U. S.'Patent No. 2,093,377, whereby prints of
remarkable properties of fastness are obtained
The following examples illustrate the invention,
the parts being by weight:—
Erample 1
, H ride with a >1:8-aminonaphtholsulphonic acid, ~ ‘
10"‘
The new dyestuiis are of "particular value in the
form of their complex metal compounds, into
which they can easily be converted by treatment
with suitable compounds yielding metal accord
W ing to known methods.v ‘
15*‘
‘
A
For example, by treatment according to the
process of British speci?cation No. 26460 / 1912 new
dyestuffs are obtained which have retained their
5 .
even with a short period of steaming.
10
23.5 parts of l-hydroxy-2-amino-4-chloroben
zene-6-sulphonic acid are diazotized in the usual
manner with 7 parts of sodium nitrite. The
diazo solution is coupled with an alkaline solu
tion of 51.9 parts of the condensation product 15
from salicylic acid sulphochloride and 1:8-amino
naphthol-3:6-disulphonic acid and the monoazo- ‘
solubility in water but contain chromium and dyestuff formed is isolated by salting out. When
still have the character of chrome mordant dye- _' dried the dyestu? is a dark violet powder which
20'» stu?s; Depending on the proportion of chromium’ dissolves in water to a blue-violet solution. On
compound used in their preparation or on the the’ addition of alkalies the solution becomes
reaction conditions, the-proportion of chromium red-violet; on the addition of acids the colour
changes towardsred. When the dyestuff is
combined with the dyestuif may vary within'cer
tain limits, either all of the groups present which printed on cotton with chromium acetate in the 25
25i are capable of being chromed or only a part usual manner,‘ blue-grey prints are obtained.
thereof being saturated-by chromium. ‘Instead Silk is dyed with ‘the dyestu?’ in combination
of chromium other trivalent metals, for example with a suitable chromium mordant in an acid
bath reddish-violet shades, which change con
iron, can be introduced into the dyestuiis.
1
.
If thedyestuffs are treated with compounds of siderably towards blue when soaped.
If a solution of the dyestufi is heated for some 30
30S, bivalent metals instead of with compounds ofv
time with a substance yielding chromium, for
trivalent metals there are also obtained water
soluble dyestu?s containing metal in complex example chromium lactate, a complex cromium
form andin part having-shades quite different compound. of the dyestu? is ‘obtained. When
from those of the parent dyestu?. They have dried this is a blue powder which is soluble in
water to a blue-violet solution. The addition of 35
, 35“?v likewise the character of mordant dyestuffs and
constitute ‘a valuable addition to thisclass of a solution of sodium carbonate causes no altera
tion in the colour; on the addition of caustic soda
the colour changes to grey-blue, whilst the addi
The new dyestu?s may also contain several dif
ferent metals simultaneously. For example, the tion of acids causes no colour change. Silk is
dyed with the dyestu? in combination with a suit
imcompounds into which a bivalent metal has al
ready been introduced can be converted by treat; able chromium mordant in an acid bath blue
dyestuffs.
.
'
V
,
.
‘
ment with a compound of a trivalent metal into
water-soluble compounds containing simultane
shades, which suiier no ' change in colour on
’ soaping.
'
If a solution of the original dyestu? is heated
with copper sulphate there is obtained a complex 45
45*‘2metal.
_
All these metal compounds are. suitable for‘ copper compound which can easily be salted out
application by the customary methods of dyeing and purified. When dried it is a red-violet pow
and printing with mordant dyestuffs on various der which is soluble in water to a bluish-red solu
tion, the colour of which is unaltered by the
?bres, such as cotton, regenerated‘cellulose arti
addition
of sodium carbonate solution. Caustic
50 J?cial silk, natural silk and, so on. Generally they
soda solution changes the colour towards blue
yield shades which are faster than those obtain
violet, whilst on the addition of acids the solu
able in‘an analogous manner with the corre
tion becomes redder. The new dyestuff contain
sponding non-metallized dyestu?s.
In particular these metal compounds can be ing copper is remarkably suitable for chrome
55-Efprinted on the ?bre in a ‘suitable manner with printing on cotton. There are produced vivid 55
ously in combination a bivalent and a trivalent
2
2,134,453
violet shades’ which are distinguished by good
properties of fastness. An addition of urea to
the printing colour results in deeper shades and
in a better ?xation with a shorter steaming period.
Fast violet tints are likewise obtained on viscose
arti?cial silk or natural silk by printing with the
dyestuff, chromium lactate and tragacanth or
gum thickening and steaming.
of which is changed towards blue-violet by the
addition of alkalies, whilst the addition of dilute
acids gives no change of the color. When printed
on cotton in the usual manner with chromium
acetate, the new copper compound yields vivid
red-violet prints, which are distinguished by good
properties of fastness. The nickel compound of
the new dyestu? behavesin a similar manner as
The new dyestu? containing copper can be
the copper compound. The copper compound is
converted by treatment with a chromium salt; ,very suitable for printing on natural silk or on 10
into a complex chromium compound containing regenerated cellulose arti?cial silk with the aid of
combined chromium in addition to copper. This
chromium lactate as mordant.
new compound is also suitable for chrome print
Example 4
ing on cotton and likewise yields violet'shades.
15
The nickel compound of the .dyestu? can be
18.85 parts. of 1~amino~2-hydroxy-3-nitro-5 15
used with advantage instead of the copper com
chlorobenzene are diazotized in the usual man—
pound. It yields somewhat reddershades on the
?bre.
.
, ner, the-solution is combined with a caustic alka
‘
Example 2
20
22.1 parts of_ the sodium salt. of picramic acid
are diazotized in the usual manner with 7 parts.
of sodium nitrite and thediazo solution is com
bined with a solution,v alkaline with sodium car
-: bonate, of 51.9 parts of the condensation product
from salicylic acid sulphochloride and 1.:8-amino
naphthol-3:6-disu1phonic acid. When dried the
new monoazo-dyestu? .is a, dark violet powder
soluble in water to a bluish-red solution. On the
addition of alkalies- the colour of the solution
changes towards red;~ dilute acetic acid causesv no
alteration in the colour, whilst dilute mineral
acids on the contrary cause a change. tov light-red.
By printing on cotton with the new dyestu? and
chromium acetate and steaming for‘ 1 hour green
ish-grey prints are obtained, whilst a shorter
steaming period- leads to dull greyish-violet prints
which- change towards red on soaping and have a
fastness .tolight and chlorine appreciably inferior
40" to that of the prints which have been steamed
for
1 hour.-
'
.
l
‘.
a
‘
By heating a solution of'the dyestuff to. boiling
with a substance yielding chromium, for example
chromium acetate, there isv obtained a complex
.. chromium compound of‘the dyestu? which can be,’
isolated from its solution by evaporation. When.
dried it is a green-grey powder soluble in water
to a blue-grey solution, the colour of, which su?ers.
no change on addition of sodium carbonate or
50-: acids, but becomes green on addition of caustic
soda. The new chromium, compound can 'be
printed on cotton in the usual manner with
chromium acetate, yielding with a'short or long
steaming period very greenish-grey prints. of good
U! in 1 fastness properties.
line; solution. of 511.9 parts of the condensation
product. from salicylic acid sulphochloride and
1:8-aminonaphthol-3:6-disulphonic acid and the 20
monoazo-dyestu? formed is isolated. by salting
out. When dried the new monoazo-dyestuif is a
greenish-blue, powder soluble in water to a red
dish-blue solution, the colour of which is changed
towards‘ light-red by the addition of acids. The 25
dyestu? yields grey-blue prints when printed on
cotton with chromium acetate in the usual. man_-,
ner. It dyes silk in the presence of a. suitable
chromium mordant reddish-blue shades‘, which
become‘ appreciably duller on soaping.
By heating a solution of the dyestu? with a
suitable substance yielding chromium there is ob
tained a new chromium compound soluble in
water to a blue solution which su?ers- no change
in colour on the addition of sodium carbonate
solution or- acids and becomes somewhat greener
on the addition of caustic soda. The new chro
mium compound dyes silk in an acid bath with
the aid of a suitable chromium mordant greenish~
blue shades, the colour of which is not changed.
by soaping.
By heating asolution of the original dyestu?
with a copper salt a complex copper compound is
obtained which is soluble in water to a’ violet. solu
tion. The solution suiTers no change in colour onv
the additionof sodium carbonate solution or; di
lute acids and becomes blue on the addition of
45; :
caustic soda solution. The new'copper'compound
dyes natural silk with the aid of a suitable chro
mium mordant vivid violet shades of good fast~ 50f
ness to light, the colour of which is not altered
by soaping.‘ The. new copper compound is also
suitable .for chrome printing on- cotton. ,
Example 5
Example 3
16.8:7 parts ‘of 5-nitro-3-amino-2--hydroxy-l-I
methyl-benzene are diazotized'in. the usualmane
60-. her and coupled under alkaline conditions witha‘
solutionof’ 51.9 parts of thelcondensation prod
uct from salicylic acid sulphochloride and 1:8
aminonaphthol-3 : ?-disulphonic acid. When dried
the new monoazo-dyestu? is a dark-violet pow
der, soluble in water to a blue-violet solution, the
colour‘ of which is changed towards red-violet by
the addition of alkalies, towards light-red by the
. 55..
233 parts of ortho-amino-para-sulphosalicyiic
acid are diazotized in the usual manner with 7
parts of'sodium nitrite and combined with a solu
tion, alkaline with sodium carbonate, of 51.9 parts
of the condensation product from salicylic acid 60
sulphochloride and 1 :.8'-aminonaphthol'-3 : 6'-di
sulphonic acid‘ to produce a monoazo-d'yestu?.
When dried the new dyestuif is a lilac coloured
powder soluble in water to a bluish-red solution
which changes towards weak yellow-red on the 65
addition of dilute acids. The dyestufi yields
violet shadeson cotton when printed in the usual
trated sulphuric acid is blue-violet. By printing manner with chromium. acetate.
on cotton with the new dyestuff and chromium. .
By treatment with a compound yielding cop
acetate and steaming for one hour reddish-grey per a red-violet dyestuff is obtained soluble in
prints are obtained.
"
.
water to a red solution which undergoes no change
The copper compound of. the¢new_ dyestu?, in colour on theaddition. of acids. When printed
which may be obtainedin theiusualf manner, is on cotton in the~usual manner with chromium
2;.so1uble in water to a red-violet 8011111011,.13'1’185001‘0111‘ acetate the. new copper compound; yields vivid.
75
addition of dilute acids. The solution in concen
3
2,134,453
very reddish-violet shades of good properties of
fastness.v
.
1
i
,
Example 6
colour of which is not changed by the addition
of dilute acids. When printed on cotton in the
usual manner with chromium acetate, the new
‘18.18 parts of 4-nitro-6-chloro-2-amino-l-hy
droxybenzene are diazotized in the usual manner
with '7 grams of sodium nitrite and the diazo.
solution is combined with a caustic alkaline solu
tion ‘of 51.9 parts or" the condensation product
from salicylic ‘acid sulphochloride and 1:8-amino
naphthol-B:6-disulphonic acid. When printed on
cotton with chromium acetate and steamed for 1
hour the dyestuff yields reddish-grey prints and
when steamed for 8 minutes dull violet prints.
By heating a solution of the dyestuff for a
15 long time with a substance which yields chro
copper compound yields vivid red-violet prints,
which are distinguished by good properties of
fastness, especially by good fasteness to washing
and light. ,
_
It is. also possible in accordance with the in
vention to prepare a large number of other
dyestuffs of which some are illustrated in the 10
following table:
Dyestuffs by coupling the following diazotized
ortho-aminophenols with the condensation prod
uct from salicylic acid sulphochloride and 1:8
aminonaphthol-3 : G-disulphonic acid:
15
mium, for example chromium acetate, there is
obtained a complex chromium compound which
Shades obtained by chrome
printing
' yields ‘neutral grey prints of good fastness prop
erties when printed in the usual manner with
20. chromium acetate and steamed for a short-or
long period.
Diazotized ortbo-aminophenol
0f the dyestu? on
cotton
7
of the copper
compound of
the dyestu?‘
20
on cotton
The copper compound of the new dyestu?,
which may be obtained in the usual manner, is
a violet powder, which dissolves in water to a
25 red-violet solution. On the addition of alkalies
the solution becomes blue-violet, whilst the addi
tion of diluted acids causes no colour change.
The copper compound of the dyestu? is remark
ably?suitable for chrome printing on cotton, re
30. generated cellulose arti?cial silk or natural silk.
There are produced vivid red-violet shades, which
are distinguished by good properties of fastness.
Example 7
‘116.8 parts of 5-nitro-3-amino-4-hydroxy—1->
Para-chloro-orthoemino salicylic acid. _
Blue-violet ________ ._
4-chloro-2-am1nophenol ______ __
Reddish grey-blue. _
5-nitro-2-aminophenol _______ __
Greenish‘blue _____ __
Violet.
Greyish-blue ______ __
Blue-violet.
Violet-grey ........ __
Recl—violet.
5 - nlitro i 4 - chloro - 2 -amino-
Red-violet.
25
Do.
eno .
4~nitro-2~aminophenoI-6~ sul-
phonic acid.
30.
Similar dyestu?s can be obtained with analo~
gous results by using in the foregoing examples
corresponding parts of 1:8-aminonaphthol-4
monosulphonic acid.
35'
What we claim is:—
1. A process for-producing mordant ortho~hy~
droxy>monoazo—dyestu?s, which comprises com
methylbenzene are diazotized in the usual man
her with r{parts of sodium nitrite and the solu
tion ‘is combined with a caustic alkaline solution
bining a diazo compound of an amine selected
of 51.9 parts of the condensation product from
salicylic acid sulphochloride and 1:8-aminonaph
thol-326-disulphonic acid. When dried the new
monoazo-dyestuff is a green~blue powder solu
stituents being selected from the group consist
ing of halogen, alkyl, carboxylic-, nitro- and sul~
from the group consisting of ortho-amino-phenol
and substituted ortho-amino-phenols, the sub 40
pho-radicals in an alkaline medium with a 1:8
tion of acids. The dyestuff yields steel-blue prints
amino-naphthol-compound substituted in the
amino group by an —SO2-aryl-ortho-hydroXy 45
carboxylic acid radical.
2. A process for producing mordant ortho-hy
in chrome printing on cotton.
droxy-monoazo-dyestuffs, which comprises com
blein water to a blue solution. The colour of
the solution becomes redder on the addition of
alkali and changes towards light-red on the addi
The chromium compound of the dyestuff pre
pared in the usual manner dissolves in water to
av reddish-blue solution which undergoes no
change on the addition of sodium carbonates
of acids, but becomes greenish-blue on the addi
tion of caustic soda solution. Fast grey-blue
‘ shades are obtained in chrome printing on cot-V
“‘ ton.
Example 8
22.3 parts of l--hydroxy-2-amino-4-chloroben
zene-S-sulphonic acid are diazotized in the usual
manner and coupled under alkaline conditions
with a solution of 51.9 parts of the condensation
product from salicylic acid sulphochloride and
l : 8-aminonaphthol-4 : G-disulphonic acid. When
dried the new monoazo-dyestuif is a dark violet
" powder, soluble in water to a blue-violet solution,
the colour of which is changed towards red by
the addition of alkalies, towards light-red by
the addition of dilute acids. The solution in con
centrated sulphuric acid is blue-violet. By print
, ing on cotton with the new dyestuff and chro
mium acetate and steaming for one hour dull,
blue-violet prints are obtained.
> The copper compound of the new dyestuff,
which may be obtained inthe usual manner, is
“ soluble in water to av red-violet solution, the
bining a diazo compound of an- amine selected
from the group consisting of ortho-amino-phenol 50
and substituted ortho-amino-phenols, the sub
stituents being selected from the group consisting
of halogen, alkyl, carboxylic- nitro- and sulp'ho
radicals in an alkaline medium with a product
of the condensation of a 1:8-amino-naphtholsu1
phonic acid with a sulphosalicylic acid chloride.
3. A process for producing water-soluble metal
compounds of mordant ortho-hydroxy-monoazc
dyestu?s, which comprises combining a diazo
compound of an amine selected from the group 60
consisting of ortho-amino-phenol and substituted
ortho-aminoephenols, the substituents being se
lected from the group consisting of halogen, alkyl,
carboxylic-, nitro- and sulpho-radicals in an al
kaline medium with a 1:8-amino-naphthol-com 65
pound substituted in the amino-group by an
—-SO2-aryl-ortho-hydroxycarboxylic acid radical
and treating the mono-azo-dyestuff thus obtained
with a'metal yielding agent._
,
4. A process for producing water-soluble meta
compounds of mordant ortho-hydroxy-monoazo
‘dyestuffs, which comprises combining a diazo
compound of an amine selected from the group
consisting of ,ortho-amino-phenol and substituted
ortho-amino-phenols, the substituents being se
70
2,134,453
lected from the group consisting of halogen, al
kyl, carboxylic—, nitro- and sulpho-radicals in an
alkaline medium with a 1:8-amino-naphtholsul
phonic acid substituted in the amino-group by an
—-SOz-aryl-ortho-hydroxycarboxylic acid radical
and treating the monoazo-dyestu? thus obtained
with a metal yielding agent.
5. A process for producing water-soluble metal
compounds of mordant ortho-hydroxy-monoazo
10 dyestu?s, which comprises combining a diazo
compound of an amine selected from the group
consisting of ortho-amino-phenol and substituted
ortho-amino-phenols, the substituents being se
lected from the group consisting of halogen, alkyl,
15 carboxylic-, nitro- and sulpho~radicals in an al
kaline medium with a 1:8-aminonaphthol-3:6
disulphonic acid substituted in the amino-group
by an —SO2~aryl-ortho-hydroxycarboxylic acid
radical and treating the monoazo-dyestuff thus
20 obtained with a metal yielding agent.
,
6. A process for producing water-soluble metal
compounds of mordant ortho-hydroXy-monoazo
dyestuffs, which comprises combinining a diazo
compound of an amine selected from the group
25 consisting of ortho-amino-phenol and substituted
ortho-amino-phenols, the substituents being se
lected from the group consisting of halogen, alkyl,
carboxylic, nitro- and sulpho-radicals in an alka
line medium with a 1:8-aminonaphthol compound
30 substituted in the amino-group by an -—SO2-sali
cylic acid radical and treating the monoazo-dye
stuff thus obtained with a metal yielding agent.
'7. A process for producing water-soluble metal
compounds of mordant ortho-hydroxy-monoazo
35 dyestuffs, which comprises combining a diazo
compound of an amine selected from the group
consisting of ortho-amino-phenol and substituted
ortho-amino-phenols, the substituents being se
lected from the group consisting of halogen, alkyl,
40 carboxylic-, nitro- and sulpho-radicals in an al
kaline medium with a 1:8-aminonaphtho1-3:6
disulphonic acid substituted in the amino-group
by an —-SOz-sa1icylic acid radical and treating
the mono-azo-dyestuif thus obtained with a metal
45 yielding agent.
8. A process for producing water-soluble metal
dyestuffs, which comprises combining a diazo
compound of an amine selected from the group
consisting of ortho-amino-phenol and substituted
ortho-amino-phenols, the substituents being se
lected from the group consisting of halogen, alkyl,
carboxylic-, nitro- and sulpho-radicals in an al
kaline medium with a 1:8-aminonaphthol com
pound substituted in the amino-group by an
—-SO2-aryl-ortho-hydroxycarboxylic acid radical
and treating the monoazo-dyestu? thus obtained
with an agent yielding a bivalent metal.
12. A process for producing water-soluble metal
compounds of mordant ortho-hydroxy-monoazo
dyestuiTs, which comprises combining a diazo
compound of an amine selected from the group
consisting of ortho-amino-phenol and substituted
ortho-amino-phenols, the substituents being se
lected from the group consisting of halogen, alkyl, '
carboxy1ic-, nitro- and sulpho-radicals in an al
kaline medium with a 1:8-aminonaphth0l com
20
pound substituted in the amino-group by an
——SO2-aryl-ortho-hydroxycarboxylic acid radical
and treating the monoazo-dyestu? thus obtained
with a copper yielding agent.
13. A process for producing Water-soluble metal 25
compounds of mordant ortho-hydroxy-monoazo
dyestuffs, which comprises combining a diazo
compound of an amine selected from the group
consisting of ortho-amino-phenol and substituted
ortho-amino-phenols, the substituents being se
lected from the group consisting of halogen, alkyl,
30
carboxylic-, nitro- and sulpho-radicals in an al
kaline medium with a 1:8-aminonaphthol com
pound substituted in the amino-group by an
—SO2-aryl-ortho-hydroxycarboxylic acid radical
and treating the monoazo-dyestu? thus obtained
35
With copper sulphate.
14. A process for producing water-soluble metal
compounds of mordant ortho-hydroxy-monoazo
dyestu?'s, which comprises combining a diazo
40
compound of an amine selected from the group
consisting of ortho-amino-phenol and substituted
ortho-amino-phenols, the substituents being se
lected from the group consisting of halogen, alkyl,
carboxylic-, nitro- and sulpho-radicals in an al
kaline medium with a 1:8-aminonaphthol com 45
pound substituted in the amino-group by an
compounds of mordant ortho-hydroxy-monoazo
dyestuffs, which comprises combining a diazo‘ —-SO2—aryl-ortho-hydroxycarboxylic acid radical
compound of an ortho~amino-phenol-sulphonic and treating the monoazo-dyestuff thus obtained
50 acid in an alkaline medium with a 1:8—amino
with an agent yielding a trivalent metal.
naphthol-3z6-disulphonic acid substituted in the
15. A process for producing water-soluble metal 50
amino-group by an —SO2-salicylic acid radical compounds of mordant ortho-hydroxy-monoazo
and treating the monoazo-dyestu?' thus obtained dyestuffs, which comprises combining a diazo
With a metal yielding agent.
compound of an amine selected from the group
55
9. A process for producing water-soluble metal consisting of ortho-amino-phenol and substituted
compounds of mordant ortho-hydroxy-monoazo
ortho-amino-phenols, the substituents being se 55
dyestuifs, which comprises combining the diazo
lected from the group consisting of halogen, alkyl,
compound of 1-hydroxy-2-amino-4-chloroben
carboxylic-, nitro- and sulpho-radicals in an al
Zene-S-sulphonic acid in an alkaline medium with kaline medium with a 1:8-arninonaphthol com
60 a 1:8-aminonaphthol compound substituted in pound substituted in the amino-group by an
the amino-group by an —SO2-aryl-ortho-hy
droxycarboxylic acid radical and treating the
-—SO2-aryl—ortho-hydroxycarboxylic acid radical
monoazo-dyestu? thus‘ obtained with a metal
with a chromium yielding agent.
16. A process for producing water-soluble metal
yielding agent.
65
10. A process for producing water-soluble metal
compounds of mordant ortho-hydroxy-monoazo
dyestu?s, which comprises combining the diazo
compound of l-hydroxy-Z-amino-4-chloroben
zene-B-sulphonic acid in an alkaline medium 1:8
70 aminonaphthol-3z?-disulphonic acid substituted
in the amino group by an -SO2-salicylic acid
radical and treating the monoazo-dyestuff thus
obtained with a metal yielding agent.
11. A process for producing Water-soluble metal
75 compounds of mordant ortho-hydroxy-monoazo
60
and treating the monoazo~dyestuff thus obtained
compounds of mordant ortho-hydroxy-monoazo
dyestuffs, which comprises combining a diazo 65
compound of an amine selected from the group
consisting of ortho-amino-phenol and substituted
ortho-amino-phenols, the substituents being se
lected from the group consisting of halogen, alkyl, 70
carbcXylic-, nitro- and sulpho-radicals in an al
kaline medium with a 1:8-aminonaphthol com
pound substituted in the amino-group by an
—-SO2-aryl-ortho-hydroxycarboxylic acid radical
and treating the monoazo-dyestu? thus obtained 75
5
2,134,453
with an agent yielding a bivalent metal and with
an agent yielding a trivalent metal.
>
17. A process for producing water-soluble metal
compounds of mordant ortho-hydroxy-monoazoe
dyestuffs, which comprises combining a diazo
compound of 1-hydroxy-2-amino-4-chloroben—
zene-6~sulphonic acid in an alkaline medium with
a 1:8-aminonaphthol-3:G-disulphonic acid sub
stituted in the amino-group by the -—~SOz-sal
icylic acid radical.
18. A process for producing water-soluble metal
compounds of mordant ortho-hydroxy-monoazo
wherein the benzene nucleus I and the naph
thalene nucleus II bear further substituents se
lected from the group consisting of halogen, alkyl,
carboxylic, nitro and sulpho, these dyestuffs con
taining copper in complex combination.
22. Water-soluble metal compounds or mordant
ortho-hydroxy-monoazo-dyestu?s, corresponding
to the following general formula:
I
OH
prism
dyestuffs, which comprises combining a diazo
compound of 1-hydroxy-2-amino-4-ch1oroben
zene-?-sulphonic acid in an alkaline medium with
a 1 :8-aminonaphthol-3 : G-disulphonic acid > sub
on lIIH—SOz-
'
10
00011
~03
n
I
stituted in the amino-group by the -—SO2-sa1
icylic acid radical and treating the monoazo-dye
stuff thus obtained with copper sulphate.
19. Water-soluble metal compounds of mordant
wherein the benzene nucleus I and the naph
thalene nucleus II bear further substituents se
lected fromvthe group consisting of halogen, alkyl,
carboxylic, nitro and sulpho, these dyestuffs con
taining chromium in complex combination.
to the following general formula:
23. The mordant ortho-hydroxy-m0noazo-dye
stuff, which may correspond to the following for
ortho-hydroxy-monoazo-dyestuffs, corresponding
'
O O OH
'
/
mula:
in ortho
O H N‘H—~S0 q-—aryl
0 H.
15
25
position to
\0 H
each other
30
II
wherein the benzene nucleus I and the naph
thalene-nucleus II bear further substituents se
lected from the group consisting of halogen, alkyl,
carboxylic, nitro and sulpho, these dyestu?s con
taining at least one metal in complex combina
tion.
'
20. Water-soluble metal compounds of mordant
'ortho-hydroxy-monoaz0-dyestu?s, corresponding
' to the following general formula:
—OH
(‘)H NH-SOz-
00011
N=NA®
45
'
'
V
OH
II
>
which dyestu?, after being dried and pulverized,
represents a dark-violet powder dissolving in
water to a blue-violet solution, changing to red 35
violet on adding alkali and to red on adding acid,
thereto and yielding, when printed on cotton to
gether
with
a . chromium mordant blue-grey
shades, when dye'd on silk in presence of the mor
dant reddish-violet shades changing towards blue,
when soaped.
24. The water-soluble copper compound of a.
mordant ortho-hydroxy-monoazo-dyestuff, cor
responding to the following probable formula:
45
‘
.
wherein the benzene nucleus I and the naph
thalene-nucleus II bear further substituents se
lected from the group consisting of halogen, alkyl,
carboxylic, nitro and sulpho, these dyestuffs con
50
taining at least one metal in complex combina
’ tion.
21. Water-soluble metal compounds of mordant
ortho-hydroxy-monoazo-dyestu?s, corresponding
to the following general formula:
'
in ortho
/
OH
position to
on NHL-soram
each other
OH
60
-N=N
’
which compound, after being dried and pulverized,
represents a red-violet powder dissolving in water
to a bluish-red solution, not changing its colour, 55
when adding a sodium carbonate solution, but
changing same towards blue-violet with a caustic
soda-solution and towards red with acid, yielding,
when used in chrome printing on cotton, natural
silk and viscose, vivid violet shades of good fast 60
ness properties.
__
MAX MULLER.
ROGER RA'I'I'I.
II
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