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Патент USA US2127478

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‘2,127,478
Patented Aug. 16, 1938
UNITED STATES PATENT oFFmE
2,127,478
ORANGE DISAZO‘ DYES'
Moses L. Crossley, Plain?eld, and. Lincoln M.‘
Shafer, Highland Park, N. 3., assignors to The
Calco Chemical 00., Inc., Bound Brook, N. J., a
corporation of Delaware
No Drawing. Application March 23, 1937,
Serial No. L132,516
4 Claims. (Cl. 260-483)
This invention relates to new azo dyes and par
ticularly to new azo dyes suitable for dyeing
wool and silk colors showing an excellent fastness
to milling.
5
5
The azo dyes of the present invention are ob
tained by coupling tetrazotized benzidine di
sulfonic acids and their‘ alkyl and alkoxy deriva
tives, with octyl phenols as the ?rst component
and naphthols such as alpha and betanaphthol,
10 naphthoic acids and naphthol sulfonic and sul
_fonic acids as a second. The benzidine compound
is usually tetrazotized in the usual manner and
coupled in alkaline solution ?rst with the octyl
phenol and then with the naphthol. The re
15 sulting dyes produce various shades of orange
on ?bers. The dyes obtained from the disulionic
acid dye Wool and silk colors that are fast to
milling, light, washing, iulling, acids and alkalis.
They discharge white when dyed on silk weighted
20 With tin.
The invention will be described in detail in
connection with the following speci?c examples
which are representative illustrations but do not
limit the invention. ‘ The parts are by weight.
25
The product is an orange powder which dyes
both vegetable and animal ?bers level tones of
orange color. It has the following structural
formula:
Example 1
17.2 parts of benzidine 3,3’ disulfonic acid are
mixed with 250 parts of water and 20 parts of
a 20% solution, by weight, of sodium hydroxide.
30 The mixture is stirred and cooled by the addition
'of ice to between 10° C‘. and 15°. C‘. 45 parts of
a 16% hydrochloric acid solution is added. The
mixture is then treated with sodium nitrite until
a positive test is secured, indicating that diazo
35 tization is complete. The excess of mineral acid
is neutralized with sodium bicarbonate. A solu
tion containing 10.3 parts of para octyl phenol,
200 parts of water, and 10.5 parts of a 20%, by
weight, solution of sodium hydroxide is added and
40 the mixture stirred for about l/z hour, or until
the octyl phenol is coupled, then a solution con
taining 7.8 parts of alpa naphthol, 30 parts of
water and 10 parts of a 20%, by weight, solution
of sodium hydroxide is prepared. ‘This is diluted
45 with water to about 150 parts. 10 parts of soda
ash is then added to this solution and it is then
added to the diazo solution. The mixture is
stirred for 12 to 16 hours and the dye salted out,
after the solution has been acidi?ed with acetic
50 acid, with sodium chloride.
>
C|)H
8/0311
I
051117
7 S/OaH
10
Example 2
17.2 parts of benzidine 3,3’ disulfonic acid are
mixed with 250 parts of water and 20 parts of a 15
20% solution, by weight,“ of sodium hydroxide.
The mixture is stirred and cooled by the addition
of ice to between 10° C‘. and 15° C’. 45 parts of
a 16% hydrochloric acid solution is added. The
mixture is then treated with sodium nitrite 20
until a positive test is secured, indicating that di
azotization is complete. The excess of mineral
acid is ‘neutralized with sodium bicarbonate. A
solution containing 10.3 parts of para octyl
phenol, 200 parts of water, and 10.5 parts of
a 20%, by weight, solution of sodium hydroxide
is added and the mixture stirred for about 1/2
hour, or until the octyl phenol is coupled, then
a solution containing 13.2 parts of Naphthol AS
(the anilide of beta oxynaphthoio acid) ,2 30
parts of water and 10 parts of a 20%, by weight,
solution of sodium hydroxide is prepared. This
is diluted with water to about 150 parts. 10
parts of soda ash is then added to this solution
and it is then added to the diazo solution. The
mixture is stirred for 12 to 16 hours and the dye
salted out, after the solution has been acidi?ed
with acetic acid, with sodium chloride.
The product is an orange-red powder which
dyes both animal and vegetable ?bers level tones
of orange-red or good fastness properties. It
has the following structural formula:
011
'
HO
l
l
S 0311
581117
25'
30
35
40
OONHCaHs
I
45
S 03H
50
2
2,127,478
This application is in part a continuation of
our earlier application, which was co-pending
herewith, Serial No. 36,122, ?led August 14, 1935
and which
has since matured into
Patent
2,075,022, issued March 30, 1937.
3. Orange to red or red-violet disazo dyes hav
ing the following formula
on/N=N_
-—N=N—ROH
We claim:
1. Orange to red or red-violet disazo dyes hav
5
S0311 S0311
ing the following formula—
R3-—-N=N—R1—R2—N:N——ROH
CsHiv
10
in which R is a naphthalene nucleus, R1—R2 is a
in which R is a naphthalene nucleus.
benzidine disulfonic acid and R3 is an octyl
4. Orange to red or red-violet disazo dyes hav
ing the following formula—
phenol.
2. Orange to red or red-violet disazo dyes hav
15 ing the following formula—
on
——N=N—~R1—Rz-—N=N——R
|
031111
C EH17
in which R is a naphthalene nucleus, and R1-—R2
is a. benzidine disulfonic acid.
15
20
where R is an anilide of an oxynaphthoic acid
and R1-—R2 is a benzidine disulfonic acid.
MOSES L. CROSSLEY.
LINCOLN M. SHAFER.
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