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Патент USA US2113029

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‘Patented Apr.
5, 1938
i
r
2,113,029;
auaozc
isms . _.~
"
Eugene A. Marhush', Jersey City, N. 1.. neither to "
Pharma ‘Chemical Corporation, New- York,
N.- Y.. a-corporation oi’ New York ‘ -
'No
Application January25,gl934,_p
Serial No. 708,31956 .'
4 Claims.
My invention relates to new coloring compounds
(Cl. 8-5)
Example 2
and refers particularly to coloring compounds
Eleven parts of the. sodium salt of 4-chlor-2
which are valuable for the printing or dyeing of
diazo-inuno-proline-anisol, 9 parts acetoacetylr
cellulose ?bers.
naphthylamine are “thoroughly mixed and they
mixture employed as follows:
'
The compounds of my invention are obtainable
by combining diazo compounds of aromatic mono
5
Two parts of the above mixture are dissolved
arnines and their substitution products, but which , in '7 parts water; 1/2 part ammonium ricinoleate,
do not contain a sulfonic group, with the aceto—
11/2 parts caustic soda solution 30 Bé., 2% parts
acetyl-naphthylamines having the formula
10
Cellosolve or denatured alcohol and the resulting 10
solution thickened to a paste with 15 parts starch
00-011‘
_
_
gum tragacanth. This paste is printed on'the
cotton cloth, and hung up to dry. The printed ~
Hr-CONHR
cloth may be developed immediately ‘after dry
ing, or the dried printed cloth stored until re -15
in which R is'a naphthalene ring which may con
tain ethoxy, alkyl,._halogen, or nitro group, or
15
groups, but not a solubilizing acid group such as quired by the printer. The developing is accom
plished- by placing the cloth in an ager :and steam- '
_ __carboxylic. or sulionic groups.
ing in the presence of acetic or formic acid vapor
The. acetoacetyl-naphthylaniines may be pro- _
for ?ve minutes. It is then soaped hot, rinsed
well and dried.
20
Where the use of an ager is inconvenient. the
duced by condensing the naphthylamines, or their
20 substituted compounds, with an alkyl-aceto
. acetate, as methyl-acetoacetate and ethyl-aceto
acetate.
developing may be done by immersing the printed '
cloth in a warm bath of, a mixture of acetic and
formic acids in the presence of Glauber’s salt.
This developing bath is heated until the shades‘ 25'
have reached maximum iullness. Furthermore,
-
The compounds of my invention may be pro
duced either in substance or upon the fiber, the
latter being capable of accomplishment by im
2
pregnating
the
fiber
with ' they . acetoacetyl
the printed material may be padded with the acid
naphthylamine compound and then treating the
mixture using the well known padding method
' thus impregnated ?ber with the diazo compound,
after which the material is dried with heat, rinsed,
or by mixing the diam-compounds in their stabi
3O
ing the stabilized form-oi one oi the compounds
the applied mixture with an acid reaction,
I-give the following as one method for the pro
duction of one of the compounds of my invention
in substance:
Example 1
of my invention upon the ?ber'z-
.
Example av
One mole of chlor-anisol-diazo-imino-alpha
Fifteen parts 01’ para-amlno-acetanilid are
amine are suspended in 500 parts of water at 40°
0., and a cold solution containing '1 parts of caus
tic soda is added. This solution is then cooled to
8° C. by addition of ice and neutralized or made
slightly acid with dilute acetic acid. '15 parts of
sodium acetate solution in 500 parts of water are
then added.
acetyl-naphthylamine are thoroughly mixed to
gether, printed upon the ?ber and developed as
described in Example 2.
Other stabilized forms of my compounds may
be employed instead of alpha-pyrrolidine car
boxylic acid such as those produced from amino—
sulfo-benzoic acid‘, methyl-glycocoll, diglycol
45
amine, amino-pyridine-carboxylic acid.
Among theshade's oi colors producibie by my
invention, I mention the, following;
The diazotized para-amino-acetanilid solution
50 is then added slowly to the solution of aceto
acetyl-p-naphthylamine under continuous agita- ‘
5
washed well to neutrality with water and dried.
I give the following as one method of develop
ing one of the compounds of my invention upon
80
the ?ber:—
_
.
I pyrrolidine-carboxylic acid and one mole of aceto
diazotized in the usual manner and neutralized
with a solution of sodium acetate.
40
Twenty-six parts of acetoacetyl-p-naphthyl
tion and the whole stirred for about two hours.
Three parts of a sodium hydroxide solution are
then added to itv very slowly and agitated for
another hour. The insoluble color is then ?ltered,
.30,
‘soaped, washed well and dried.
'
I, give the following as one method of employ
lized form with the acetoacetyl naphthylainine
compound, applying it to the ?ber‘ and treating
Diazotized amine
-
Coupling component
Shade
50
2,6 dichloro-aniline .............. -_ Acetolaacgyl-c-na'ph- Yellow.
y
e.
,
'
>
p-Nitro-toluidine ............... -. AcetoaoetyM-mphe
thylamine.
Do.
-
'
,
'
p-Amino-phonyl-benzyl-ether...... Aoetoacetyl-a-naph- Greenlah
thylamino.
v,
~
Chloranisidino ............... .4... Aoetoecetyl-chlor-?
‘
'
naphthylamine.
Chloranisidine ................. .'.. 'Acetoacetyl-c-naph,
thylaminc.
llow.
'
‘
0.‘.
,
~‘
Do.
I
I do not limit myself to the particular chemi
'
-
2
2,118,029
cals, quantities, times, temperatures or steps of
a basic paste. containing a water-soluble diazo
procedure as set forth as these are given simply
as a means for clearly explaining my invention.
What I claim is:
imino derivative of 3-chlor,-_6_-methoxyaniline and
1. The method of dyeing a cellulosic material
which comprises impregnating the material with a
basic paste containing awater-soluble diazo-imin‘o
‘ derivative'of aniline and a non-substantive aceto
acetyl-naphthylamine and subjecting the im- ’
10 pregnated material at elevated temperature to the
action of a mild acid.
‘
2. Themethod of dyeing a cellulosic material
which comprises impregnating the material with
a non-substantive acetoacetyl - naphthylamine
and subjecting the impregnated material at ele
vated temperature to the action of a mild acid.
‘3; A cellulosic textile fabric dyed with the cou
pling product of a diazotized aniline and a non
substantive aceto-acetyl-naphthylamine.
4. A cellulosic textile fabric dyed with the cou
pling product of a diazotized 3-chior-6-methow
aniline and a non-substantive aceto-acetyi
naphthylamlne.
.
EUGENE A. MARKUBH.
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