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Патент USA US3023230

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United States Patent 0
er“
3,023,220
'
ICC
Patented Feb. 2?, 1962
1
2
C. with '10 parts of sulfuric acid 96%. Stirring at 20
3,023,220
25° C. was continued for 1 hour or until a golden brown
coloration was observed. When carbazolation was
PROCESS OF PREPARING ANTHRAMID
VAT DYESTUFF
complete, as indicated by a color change from yellow
green to golden brown, 1.3-1.6 parts of water were add
Joseph S. Milazzo, Palisades Park, N.J., assignor to Gen-v
eral Aniline & Film Corporation, New York, N.Y., a
corporation of Delaware
No Drawing. Filed Oct. 22, 1959, Ser. No. 847,879
2 Claims. (Cl. 260-316)
ed as the temperature rose to 60°—65° C. but not over
80°—85° C. After the water addition was made, the
mixture was stirred at 60°-65° C. for 2 hours. The
mass was then poured into 36-40 parts of water to pre
This invention relates to an anthamid vat dyestuif and 10 cipitate the dyestu?'. The mixture was heated to 60°
85° C. and puri?ed by adding 0.25 part of sodium bi
particularly to an improved process of preparing Indan
chromate. It is then ?ltered and washed neutral with
threne Olive R (yellow shade).
water. The dyestutf obtained dyes cotton an olive shade
It is known that an olive-gray vat dyestutt can be pre
pared by the treatment of dibenzoyl-p-p'-diamino-a-eU-di
with a yellow cast (substantial) when compared to In
anthramid with concentrated sulfuric acid. The proce 15 danthrene Olive RAP Dbl Pst new; Color Index 1150.
dure which is more fully disclosed in United States Pat
Example II
ent 996,109 involves the heating of 1 part of‘ the said
1 part of l,l’-iminobis-(4-benzoylamino anthraqui
di-anthramid with 10 parts of 66° Be. sulfuric acid with
none) produced by condensing benzoyl chloride and 1,
stirring to 30-35° C. until the mass has assumed a bro-wn
coloration. 10 parts of a 40% fuming sulfuric acid are 20 1'-irninobis (4-arninoanthraquinrne) was stirred at 20"
25° C. with 10 parts of sulfuric acid 96%. Stirring at
then added and the mixture poured on ice. The dye,
which separates in the shape of olive-green ?akes, is ?l
tered oil and then washed with water.
20°-25° C. was continued for 1 hour or until a golden
brown coloration was observed. When the carbazola
'
tion was complete, as indicated by a color change from
It is also known that in the preparation of the anthra
rnid dye by carbazolation, ring closure is resorted to by 25 yellow green to golden brown, 1.3-1.6 parts of Water
were added below 20° C. After the water addition,
treatment with sulfuric acidat low temperatures i.e., be
the mixture was heated to 60°-65° but not over 80°
low 15°-25° C.; Chemistry of Synthetic Dyes and Pig
85° C. and held for 2 hours. The mass, was then poured
ments by H. A. Lubs, page 464. The low temperatures
into 36-40 parts of water to precipitate the dyestu?’. The
are employed to prevent hydrolysis of the benzamido
groups and to eliminate low yields and low dyeing strength 30 mixture was heated to 60°-85° C. and puri?ed by add
ing 0.25 part of sodium bichromate. It was then ?l
of the olive-gray dyestu?.
tered and washed neutral with water. The dyestuff ob
I have made the surprising discovery that the anthra
tained dyes cotton an olive shade with a yellow cast
mid dyestu? can be readily prepared in a much more
facile and economical manner by conducting the carbazo
(substantial) when compared to Indanthrene Olive
lation, ring closure, at 20°-25° C. and eliminating the 35 RAP Dbl pst new, Color Index 1150.
use of 40% fuming sulfuric acid. After the ring closure
Example 111
is complete, indicated by a color change in sulfuric acid
from yellow green to golden brown, water is added as
1 part of 1,1'-iminobis-(4-benzoylamino anthraqui
the temperature rises to 60°-65° C. but not over 80-85°
none) produced by :cndensing benzoyl chloride and 1,1’
C. to give a microcrystalline product when examined un 40 iminobis (4-aminoanthraquinone) was stirred at 20°
der the microscope. The acid mixture is then precipitat
25° C. with 10 parts of sulfuric acid 96%. Stirring 20°
ed in water and given a sodium bichromate puri?cation.
25° C. was continued for 1 hour or until a golden brown
coloration was observed. When the carbazolation was
Then, the puri?ed dyestutf is ?ltered, washed neutral.
The dyestuif produced dyes cotton from an alkaline hy
complete, indicated by a color change from yellow green
drosul?te vat fast olive-gray shade substantially yellower 45 to golden brown, 1.3-1.6 parts of water were added be
than Indanthrene Olive RAP Dbl pst new; Color Index
low 20° C. After the water addition, the mixture was
1150. This discovery is of great economic signi?cance
heated to 35 °-65° C. and 0.14 part of manganese dioxide
since the uses of Indanthrene Olive R are numerous, such
added.
The mixture was stirred at 35°-65° C. for 2-4.
'as'in self shades and also in mixed browns which make
hours. The resulting mass-was poured into 36-40 parts
for considerable reduction in the cost of producing the 50 of water to precipitate the dyestuff. ,_ The mixture was
mixed browns.
.
heated to 60°-85° ;C. and puri?ed byfadding 0.25 part
In accordance with the present invention, it is interest
of sodium bichromate. It was then ?ltered and washed
ing to note that when the sulfuric acid concentration is
neutral with water. The dyestu? obtained dyes cot
reduced by the water addition to about 80-85% (after
ton an olive shade with a yellow cast (substantial)
the carbazolation step), no hydrolysis of the fbenzamido 55 when compared to Ind. Olive RAP Dbl pst new; Color
groups were noticed since high yields, were.v obtained _, . Index 1150.
(about 95% of'theory based on color value). ‘ All fast-v '
I
ness properties, chlorine, light and wash are excellent.
when compared to Ind. Olive RAP Dbl pst new; Colorv
60
Index 1150.
The following examples will more fully describe the
improved process of the present invention. .All parts
claim:
’
.
(benzoylamino)'-carbazole vat dyestu? which - consists
treating l,l'-iminobis - (4 - benzoylaminoanthraquinone)
‘with 96% sulfuric acid at about room temperature for a
period of time to yield a golden-brown coloration, adding
sut?cient water'as'the temperature rises'to between 60
Example ‘I
85° C. to yield a‘ microcrystalline product, precipitating
65
' A 1 part of 1,1'-iminobis-(4-benzoylamino anthraquinone) ‘
the sulfuric acidmixture in water and adding sodium
produced by condensing benzoyl chloride and l,l’-imido
'bichrornate to purify the same followed by- ,isolation of
given are by weight.
- I
his (4-aminoanthraquinone) was stirred at 20°-25°
'
l. The process of preparing 1,2,7,8-diphthaloyl-3,6-di>
l‘. the puri?ed vat dyestutf by ?ltration.
2. The process of preparing 1,2,7,8-diphthaloy1-3,6-di(benzoylamino) carbazole vat dyestu? which consists
References Cited in the ?le of this patent
UNITED STATES PATENTS
treating 1 part by weight of 1,l'-iminobis-(4-benzoylam
inoanthraquinone) with 10 parts by weight of 96% sulfur-
1’885’172
Baumann ----------- "" Nov- 1’ 1932
ie acid at about room temperature for a period of time to 5
2,278,973
Cm ------------- -" Apr‘ 7’ 1942
505,584
Great Britain _________ ___ May 12, 1939
yield a golden-brown coloration, adding from 1.3 to 1.6
parts by weight of water, maintaining the temperature be-
FOREIGN PATENTS
tween 60-85° C., pouring "the sulfuric acid mixture into
water and adding 0.25 part by weight of sodium bichromate, and isolating the said dyestuff by ?ltration.
10
OTHER {{EFERENCES
Ve?kataramani synthetlc Dyes, Vol- 11, P- 900 (1952)
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