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Патент USA US2124238

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2,124,238 ’
Patented July 19, 1938
PATENT» OFFICE
“ ‘u~UNITED71STATES
2,124,238
PROCESS FOR PRODUCING 'PYnImNo-AN
THRAQUINONE DERIVATIVES AND PROD‘
UCTS THEREOF
Heinz Scheyer, Frankfort-on-the-Main, and Emil
Frankfort- on-the-Main-Fech
~ Schwamberger,
enheim, Germany, asslgnors to'General Aniline
Works, Inc., New York, N. Y., a corporation of
Delaware
No Drawing. Original application May ‘6, 1936,
; Serial No. 78,224.
.
October 2,
Divided and this application
1937, Serial No. 167,022. In Ger
many ’May 16, 1935
,‘3 Claims. (01. 260—_-40)
The condensation products thus-obtained are A
The present application is a division of our ap
valuable intermediates for the production of dye- ‘
stuffs, particularly, so far as they contain the
radicle of a vattable amine, they are dyestuffs
plication Serial No. 78,224, ?led May 6, 1936,
which relates to a process for producing con
densation products of the anthraquinone series.
themselves of a good tinctorial power and good
fastness properties.
The process described. and claimed therein com
prises acting ‘in an organic solvent and in the
presence of strong alkaline ‘acting agents with
primary aromatic amines of the benzene, naph
thalene and anthraquinone series'on 1.2-benzan
In order to further illustrate our invention the
following examples are given, the parts being
by weight and all temperatures in degrees centi
grade.
_
10
‘
Example 1
Our present invention'relatesito a process for
"A mixture of 3 parts of 1.2(N)-pyridinoan
. producing condensation products of the anthra
quinone series. The new process comprises act-“ thraquinone, 2 parts of 2-nitraniline, 15 parts
ing in an organic solvent and in the presence of of caustic potash and about 60 parts of pyridine
10
thraquinones.
.
.
strong alkaline acting agents with primary aro
matic amines on pyridino-anthraquinones of ‘the
general formula:
.
is stirred for about 24 hours at about 50°. The
15_
separated reaction product is ?ltered off, washed
1 and dried. It crystallizes from chlorobenzene in
orange-red crystals, soluble in concentrated sul
furi'c acid with a violet color turning to blue when 20
‘adding paraformaldehyde. The condensation
product corresponds to the formula:
"20
0
25
wherein one X stands for CH and the other X
stands for N.
I
V
As primary aromatic amines those of the ben
zene, naphthalene and anthraquinone series
which may contain besides the amino group fur
\N11
N02
vatted.
sponding amount of 5-chloro-2-aminobenzoic
The reaction probably takes place in such a
manner that the amino group reacts, while split
ting off hydrogen, with the anthraquinone nu
pyridino-anthraquinone and 1-amino—anthra—
quinone probably corresponds with the formula:
30
By treatment with sulfuric acid monohydrate at
mary amines of ring systems capable of being
cleus. So the condensation'product of 1,2(N)
40
25
,
room temperature a sulfonic acid is formed which
dyes wool from an acid bath orange shades.
When replacing Z-nitraniline by the corre
ther substituents are suitablayparticularly pri
[35
N
/
acid a Violet carboxylic acid is obtained which
yields an orangebenzacridone by treatment with
chlorosulionic acid.
Example 2
A mixture of .3 parts of 1.2(N)‘-pyridinoan
thraquinone, 2 parts of Z-naphthylamine, 10
parts of ?nely powdered caustic potash and about
40
60 parts of pyridine is stirred for about 12 hours 45
45
at room temperature. ‘ The condensation product
thus obtained of the‘ formula:
'
50
:50
2,124,238
forms when recrystallized for instance from
chlorobenzene bluish red needles, soluble in con
centrated sulfuric acid with .a greenish yellow
color turning to blue when adding paraformalde
When
condensing
in
the
same
manner
1 (N) ,2-.5 (N) ,G-di-pyridinoanthraquinone
with
two,molecular proportions of l-aminoanthra
quinone a red dyeing vat dyestu? is obtained.
hyde.
Example 5
at By
about
treatment
50° a sulfonic
with concentrated
acid'is obtained
sulfuric
dyeingacid
the 1
i "-Ai‘mixtur'e of 2.6 parts of 1.2(N) -pyridinoan
animal ?bers from an acid‘ bath bright bluish
red shades.
thraquinone, 3.6 parts of l-amino-ll-benzoyl
aminoanthraquinone, 10 parts of caustic potash
Example‘ 3
and about 80 parts of pyridine is stirred for some 10
time at about 50°. The liquor becomes bluish
colored and the formed condensation product is
A mixture of 2.6 parts of 1.2(N)-pyridinoan
thraquinone, 2.5 parts of l-aminoanthraquinone, '
5 parts of powdered caustic potash and about 40
15 parts of pyridine is stirred for about 5 hours at
about 50°. The condensation product formed of
the formula:
isolated. It corresponds to the formula:
15
6
' -
n
20
25
30
crystallizes from highly boiling organic solvents
such as nitrobenz'ene in bright red needles.
It
I
O >
and is identical with the product obtainable by
condensing 3-bromo-1.2 (N) -pyridinoanthraqui
none with 1-amino-4¢benzoyl-aminoanthraqui
none; It crystallizes from .dichlorobenzene and
dissolves in concentrated sulfuric acid with. a
dissolves in I concentrated sulfuric acid with a
yellowish green color.
blue, in sulfuric acid of 80% strength ‘with a red
In this case, the splitting of hydrogen is
advantageously carried out in the presence of an
color and dyes cotton red shades of a good fast
ness to chlorine and boiling carbonate solution.
The product is identical with the ‘condensation
product obtained by condensing 3-bromo-2 (N) -1
pyridinoanthraquinone vwith l-iaminoanthraqui
none.
When using as one reaction’ component ‘an
1.2(N) -pyridinoanthraquinone
derivative,
the
py-2-position of which is substituted by the 2.6
dichlorophenyl radicle, a’ somewhat more bluish
red dyestuif is obtained.
45
’
HsCu-CO.HN
'
V
oxidant, for instance by passing air through the
reaction mass.
.E'xample 6
A mixture of 2.6 partsof 1.2 (N) -pyridinoan—
thraquinone, 2.3 parts of Z-aminoanthraquinone,
10 parts of ?nely powdered caustic potash and
about 60 parts of pyridine which is free from Wa
ter is stirred for about 24 hours at room temper
ature. The condensation product formed of the
formula:
45
‘ Example 4
A mixture of/2.6 parts of 1»(N)_.,--2-pyridinoan
50
thraquinone, 2.5 parts of l-aminoanthraquinone,
0It
3 parts of powdered caustic potash and about 30
parts of alcohol is boiled for‘ about 6 hours in~a
/\
/
r
\NH
.
vessel provided with a stirrer and Ya re?ux con
denser.
55
The precipitate formed is isolated and
may be‘sepa'rated' from some unchanged initial
products by extraction with organic solvents such
as'chlorobenzene. It crystallizes from nitrobené
zenefdissolves in concentrated sulfuric, acid with
a pure blue color and dyes cotton from a yellowish
red vat red shades ofi‘a more‘ yellowish tint than
the product of the foregoing example.’ The new
compound corresponds to the‘ formula:
I
I
N
0II
~
r
55
dyes cotton'ifro'm the vat red shades‘.
We claim:
it
_
_
‘ l. A process‘ for producing‘ condensation prod
ucts of the anthraquinone series which comprises
acting in an organic solvent and in the presence 60
of strong ‘ alkaline acting agents with‘ primary
amines of the benzene, naphthalene and anthra
quinone series on pyridino-anthraquinones of the
general formula:
‘
65.
wherein one‘X stands'for CH and the other X
stands for N.
i
75
2,124,238
2. The vat dyestu? of the formula:
5
'
3
3. The vat dyestuff of the formula:
o
-
5
2x
--—NH (I)
10
.
'
10
which vat dyestu? dyes cotton from the vat red
1r
‘
"- which vat dyestu? dissolves in concentrated sulfuric acid with a pure blue color and dyes‘cotton from a yellowish red vat red shades.
shades.
,
I-IEINZ SCHEYER.
EMIL SCHWAMBERGER.
15
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