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Патент USA US3090790

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3,090,780
United States Patent 0 MICC
Patented May 21, 1963’
1
2
the invention however without limiting its scope.
parts are by wtight unless otherwise indicated.)
3,090,780
DISAZO DYES
Ermannn Gaetani, Milan, Italy, assignor to Aziende
Colori Nazionali Atiini Acna S.p.A., Milan, Italy, a
corporation of Italy
N0 Drawing. Filed Apr. 14, 1960, Ser. No. 22,124
Claims priority, application Italy Dec. 15, 1959
6 Claims. (Cl. 260-186)
Example 1
16.1 g. m-tri?uoro-methyl-aniline are d-iazotized in a
conventional manner and are coupled with a solution of
25 g. of the sodium salt of 3-methylaniline omega-methane
sulfonic acid vdissolved in 300 g. water in the presence of
50 g. sodium acetate at a temperature lower than 10° C.
An object of the present invention is to provide certain
new water insoluble disazo dyes comprised in the general
Formula A:
OF;
I
(All
The mono<azo dye thus obtained is ?ltered, washed, and
suspended in 250 g. ethanol and 20 g. sodium hydroxide.
solution (36 Bé.) and then heated to the boiling point
CH3
for 1 hour. It is then cooled, diluted with water and 4
amino~2-methyl-3’-tri?uor0methyl aZo-benzene is ?ltered
and recrystallized from alcohol (meling point: 114—115°
(A)
C.). 27.9 g. crystallized amino-azo compound are di
azotized ‘in 400 g. water and 35 g. hydrochloric acid solu
tion by adding 7 g. sodium nitrite dissolved in 20 g. water,
with an alkyl group and X is selected from the group con
20 and keeping the temperature below 10° C. The diazo-azo
sisting of hydrogen and a dialkylsubstituted amine.
compound thus obtained is coupled with a solution of 12
The dyes of the above mentioned general Formula A
g. 4~methyl~phenol dissolved in 200 g. water and 14 g.
are suitable for the direct dyeing of polyole?n materials
sodium hydroxide solution, While also adding 50 g. sodium
by simple application at the boiling temperature of the
acetate, and keeping the temperature at about 10° C.
dyeing bath.
When the coagulation is completed the mass is brie?y
Among the dyes of general Formula A, the following
heated to 60° C. The precipitated disazo dye is ?ltered
dyes have shown to be particularly suitable for dyeing
off, washed with cold water until it is neutral, and ?nally
polypropylene and polyethylene materials:
dried, thus obtaining a dye in the form of a brown powder
wherein Ar is selected from the group consisting of hy
droxy phenyl and hydroxy naphthyl, further substituted
(I) F 3
(EH;
0 Ha
(melting point: 170° C.) corresponding to the formula:
CF14
OH;
I
I
OH
C F3
(EH;
0H
35
Upon examination by paper chromatography the dye gives
a uniform yellow spot which turns to red by treatment
with alkalies, but remains unaltered with acids.
C F3
40
('3 H3
Example 2
27.9 g. 4-amino-2-methyl-3'-tri?uoro-methyl-azo-ben
zene are diazotized as in Example 1.
(I) F 3
(1) H3
The diazo-azo
compound thus obtained is coupled with a solution of
45 15.5 g. ?~naphthol in 100 g. water, 7 g. sodium hydroxide
and 18 g. 30% ammonia. At the end of the coupling
0H
the disazo dye obtained, having the formula:
in
50
C Ha -
(I) H
i
0 H3
O 2115
“ is ?ltered oii, Washed, and dried, thus obtaining a dark
red powder (melting point: 201° (3.). Upon examination
by chromatography a uniform red spot which remains
unaltered with either acids or alkalies, is noted. When
,e-naphthol is replaced by the same amount of u-naphthol,
a dye is obtained which has the formula:
The compounds of general Formula A are obtained
by coupling in the presence of a strong base, one mol of
an amino azo compound of the type:
CF;
l
CF3
CFQ
l
/
l
R
CFa
I
R
wherein R is hydrogen, with one mol of a compound of
the type:
(melting point: 212° C.). Upon chromatography, this
HAr—X
dye appears as a violet red spot which turns to blue with
.
.
wherein Ar and X have the above ment1oned meamng.
The following examples are given to further illustrate
10
alkalies, but remains unaltered by acids. In contrast,
by coupling with a solution of 17.5 g. 1-methyl-4-naphthol
3,090,780
4
and
instead of the a-naphthol, the following dye is obtained
under the same conditions:
(11F;
C F3
CH3
OH
C H3
1
ON: Gala
’
/G2Hs
C 1115
OH
$11,
(melting point: 215° 0). Upon chromatographic exami
10
2. A disazo dye, insoluble in water, having the follow
ing vformula:
OF;
nation, this forms a violet-red spot, which is more violet
than that of the dye prepared using u-naphthol, but has
(‘3113
$113
the same chromatic reactions.
Example 3
15
27.9 g. 4-amino-2-methyl-3'-tri?uoro methyl-azo~ben
3. A disazo dye, insoluble in water, having the follow
zene are diazotized in a conventional manner and the
ing formula:
diazo-azo compound obtained is coupled with a solution
of 18 g. N,N-diethyl-meta-aminophenol in 200 g. water
CH3
IC F a
l
O H.
and 15 g. hydrochloric acid solution. After addition of 20
the diazo compound, a 50% aqueous sodium acetate solu
tion is gradually added until the mass does not exhibit
any acid reaction with Congo red indicator.
The disazo dye obtained is ?ltered, washed and dried.
This dye has the formula:
'
25
4. A disazo dye, insoluble in water, having the follow
ing formula:
30
(melting point: 145° C.) gives by chromatography a uni
form scarlet spot which turns to violet either with alkalies
or with acids.
Having thus described my invention, what I desire to 35
secure and to claim by Letters Patent is:
5. A \disazo dye, insoluble in water, having the follow
1. A disazo'dye, insoluble in water, selected from the
group consisting of dyes of the ‘formulae:
(IJH:
OH
0 F;
I
CH3
I
ing formula:
40
45
0H3
|
6. A disazo dye, insoluble in water, having the follow
ing formula:
50
? F3
am
‘21*
\
OH:
V
V
H
55
References Cited in the ?le of this patent
UNITED STATES PATENTS
0 Fa
|
C H:
I
OH
l
60
2,120,743
2,126,841
2,618,630
Graenaeher et a1 _______ __ June 14, 1938
Thurm ______________ __ Aug. 16, 1938
Dickey ______________ __ Nov. 18, 1952
200,533
201,838
Switzerland ____________ __ Jan. 2, 1939
Switzerland __________ -_ Mar. 16, 1939
FOREIGN PATENTS
6
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