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Патент USA US2115852

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Patented May 3, 1938
1 ‘2,115,852
UNITED STATES PATENT OFFICE’!
AZO DYES
Chester w. Hannum and Swanie s. Rossander, ' Wilmington, DeL, assig'nors to E. I. du Pont de
Nemours & Company, Wilmington, Del., a.
corporation of Delaware
-
' _No Drawing. Application July 8, 1937,
Serial No. 152,527 .
4 Claims.
This invention relates to blue and violet dyes
(Cl. 8-5)
‘
with a dyestuil! represented in'the form of- it
of the azo class and 'to means of producing and
free acid by the formula:
,
' applying them.
I
The prior art discloses blue and violet dyes of
a type bearing a super?cial similarity to the dyes
of this invention.‘ In German Patent 163,321
(1905), for example, are dyes which have fair
utility but are lacking in su?lcient fastness to
.
-
Y
Y
Y
Y
(3028): v
washing, whereby the utility is greatly diminished.
'10
It is an object of this invention to produce new
dyes of blue and violet ‘shades which have ex
ceptional fastness to washing and which are also
in which aryl is one of the group consisting of
benzene and alpha-naphthylamine, at least one 10.
fast to light, heat, chlorine, and the other in
?uences which a?’ect the permanence of dyes.
The objects 01' the invention are attained,
generally speaking, by manufacturing and apply
ing to the ?ber by development thereon the class
group from the class consisting of carboxylic acid I
and suli’onic acid, E is one of the group consist
of colors represented by the formula:
of the said aryls having a water-solubilizing
ing of benzene and phenyl pyrazolone, ‘having a
free amino group, and Y is at least one of the I
‘
group consisting of hydrogen, alkyl, alkoxy, and
halogen, diazotizing and developing with beta
naphthol, preferably, or with phenyl-pyrazolone,
acetoacet-arylide, and meta-tolylene-diamine, or
with a benzene or naphthalene compound capable
of coupling.
‘
.
‘
‘
The following examples illustrate the inven
. tion but do not limit it.
25
I
Example!
-
-
I
'
Five parts of cotton piece goods are dyed in the
Y
usual‘ manner known to those in the art with four
80 in which aryl is one of the group consisting of
' ' benzene and alpha naphthylamine and in which
at least one “aryl" has a water-solubilizing sub
stituent, E has a single nucleus from the group
consisting . of benzene and phenyl-pyrazolone,
35 Z has a single nucleus from the group consisting
of beta-naphtha],
phenyl-pyrazolone, meta-'
tolylene-diamine, and acetoacet-arylide, and Y is
hundredths part of H-acld-mlpha naphthyla
mine—>1,6-Cleves acid->cresidine. The dyed fab
ric (blue in shade) is rinsed in cold water and put
in a casserole with 200 parts of water at 120° G.
Add three-tenths part ofsodium nitrite and four
tenths part of sulfuric acid. Stir 15 minutes.
Rinse with cold water. Dissolve one-tenth part
of Z-naphthol in 200 parts ofwater and one 85
twentieth part of caustic soda.
Stir the solution -
one or more of the group consisting of hydrogen, rapidly while adding the above rinsed piece goods.
Stir for 15 minutes. Rinse in cold water and dry.
40 alkyl, alkoxy, halogen, carboxy, and sulfonic acid.
The dyeing is a blue shade.
The dye is applied to the ?ber by directidyeing formula of the dye on the iiber is:The‘ probable
S OrNB
.
.
N=
N=N
N=1~l
OaNa
'
.
0
"
i
'
_
0mg.
'
'
arrests _
Shade
Coupling component
Diem component
‘
_
on
cellu
lose
-naphthyiamine—>i,6-Olevee acid—-—-)
Beta-nsphthoi ................ -- Blue.
.
Vioiet.
Do. '
Biu .
Do.
10
Do.
Glevu acid-4
- naphthyiamine—>l,6 - Oleves acid-r
Do.
-naphthyiamine—-)l,6 - Cieves ldd-——)
Do.
Cloves acid-e
Do.
- Cleves acid-e
Do.
v15
Do.
Do.
Cloves acid->1, G-Cleves
20
1,6 -
25
In the foregoing tablethe arrows mean ‘coupled ' nucleus from the group consisting. of benzene and
by the diazo reaction.
.
30 ' These colors‘ have excellent shades of blue and
violet and outstanding fastness to washing and
‘ outstanding discharge properties.
They are also
fast to the usual destructive in?uences and ac
cordingly are superior colors.
,
At least one of the center nuclei must contain a
water-solubiiizing group, such as suifonic or'car
boxylic acid and two such groups are often of
assistance. Each of the aryl nuclei may also
' phenyl pyrazolone, Z has a single nucleus from
the group consisting of beta-naphthol, l-phenyl- _
3-_methyl-5-pyrazolone, meta-tolylene diamine,
acetoacet-arylide, and Y is one or more of the
group consisting of hydrogen, alkyl, alkoxy,
halogen, carboxy, and sulfonic acid.
3. The compound representedin the form of a .
its free acid by the formula:
contain one or more substituents from the group
consisting of hydrogen, halogen, alkyl, alkoxy, .
carboxy. and sulfonic acid.
OH
As many apparently widely diiierent embodi
ments of. this invention may be made without de
parting from the spirit and scope thereof, it is
to be understood that we do not limit overselvcs in which aryl is one of the’ group consisting of
45
benzene and alpha'naphthylamine and in which '
to the specific embodiments thereof except as de
at
least one “aryl” has a water-s'olubilizing sub
?ned in the appended claims.
stituent, E has a single nucleus from the group
We claim:
.
1. The compound represented in the form of consisting. of benzene and phenyl-pyrazolone, Z
has a single nucleus from the group consisting of
its sodium salt by the formula:
40
I
Y
.
50
BOaNa
03
55
N:
OsNl
8.4%“?
2. The compound'represented in the form of its
beta-naphthol, phenyl-pyrazolone, meta-tolyl
ene-diamine, and acetoacet-arylide, and Y is one
free acid by the formula:
(30x3); 2
70
80:3
in which a l is one of a group consisting ‘of * or more of the groupv consisting of hydrogen,
benzene
and aipha-naphthylamine, E has a single aikyl, alkoxy, halogen, carboxy, and sulfonic acid.
18
2,115,852
4. The process which comprises dyeing cellu
lose with a compound representedin the form of
itsfree ‘acid by the formula:
5
'
I
|
on
‘f
‘If
N=N--ary1—N=N—aryI-N=N~E
—
Y
(H038);
3
group from the class consisting of carboxylic acid
and sulfonic acid, E is one of the group consisting
of benzene and phenylpyrazolone, having a free
amino group, and Y is at least one of the group _
consisting of hydrogen, alkyl, alkoxy, and halo
gen, diazotizing the color on the ?ber, and
coupling it to one of a groupof compounds con
sisting of 'beta-naphthol, ,1-phenyl-3-methy1-5
pyrazolone, meta-tolylene-diamine and acetoaceté
10
arylide.
in which aryl is one of the group consisting of "
benzene and alpha-naphthylamine, at‘ least one
of the said aryls having a. water-solubilizing
|
_
’
-
'
10
_
CHESTER W. HANNUM.
SWANIE S. ROSSANDER.
'
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