Note: Descriptions are shown in the official language in which they were submitted.
7~
The present inventio.n .relates to a.new valuable
monoazo dye, to a process for the preparation of this dye, and
to the application of the dye i.n equalized dyeing of sy.nthetic
pol~a~ide fibers. .
rrhis inve.ntio.n relates to a novel dye havi.ng the
following structural formula:
CN
~ ~ ~ N=N ~ ~ / 2H5 ~I)
=/ C2H5
1 N OCH2CH2-COOH
~his dye may be used i.n the dyei.ng of various kinds of synthetic
fibers, for example, fibers made of po:Lyester, cellulose esters
or ethers, polyacrylonitrile, acrylo.ni-trile copolymers, etc.
However, the preferred use of the dye ls in the dyeing of sy.nthe-
tic polyamide fibers such as, e.g., fibers made from hexamethylene-
di.amine adipate, poly- ~-caprolactams, polyco~ndensates of omega-
amino-undecanoic acid, and the like, as well as from polyurethanes. -
As regards sy.nthetic polyamide fibers, dye (I) is
suitable for dyeing all articles made of co.ntinuous filaments 9
e.gv, stockings, knitwear, conti~uous thread fabrics, etc. : ~-
As is known, synthetic polyamide fibers are freque.ntly irregular
or ~on-~niform i.n their chemical structure (e.g., due to non-
homogenuity in the distribu-tio.n of the basic e.nd groups). In
additio.n, polyamide fibers often exhibit variatio.ns in their . -
chemical-physical and physical state, e.g. 9 differe~ces in their
morphological states, variations in crystallinity, diflere~nces
i.n surface struc-ture and in the microporosity of the fibers.
All of the above differe~ces giYe rise to differences in-.the
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distributio:n of the dye in the fi.beris, 30 that there are
di.ffere.nces i.n their behavior under li~ht as a result of diffusion
and absorption phenome.na.
'~he tintorial characteristics of dye (I) are unusually
good.
It is known that in the dyeing of synthetic polyi~mide
fibers, which are i.nvariably more or less "streaked", the fibers
exhibit differing requirements as reg~rds the various dyes.
As a matter of fact, the dlspersed dyes such as, e.g.,
the "Microsetile" clyes (registered trademark of Montedison),
may co.nveniently be used for the productio.n of light colors
inas~uch as they ha~e a high co~ering power for irregularities
of the fibers (streaks). ~ s
I.n the productio.n of medium or full colors, one must
keep in mind, apart from the virtual impossibili-ty of obtaining
very i.ntense dyei.n~s with dispersed dyec, their poor fast.ness
to wet treatments.
0.~ the other hand, most of the anio.nic dyes, such as,
e.~., "Nailammide" dyes (trademark of Montedison) offer good
poissibili-ties for the production of dark colors, moderate
possibilities ~or medium shades, and in general they are not
suitable fox the productio.n of light shades because of their . .
i.nsufficie.nt leveling power. .:.~
.
~he dyeings of sy.nthetic polyiamide fibers resulting ~ :
from the application of dye (I) are particularly valuable because
: . ..
of their fastness and resistance to light and to perspiration, . :
i as well as because of the brightness of the color shade~ j :
This result was altogether unexpected inasmuch as the
i
isomer of dye (I), which isomer is of the formula (II) below . : .
' ~ .
.
- 2 - -
.
, .. . . . .. .
.,.:. ~ . . . .. . . . . .
, . : ~ . . ~ : . .. . . . .
:,. . . , :. . .
7~7r7
Cl
NC ~ N N~ N \ (II)
C2H5
NHCOCH2CH2-COOH
imparts to polyamide fiber~ a fastmess to light, perspiration,
and an equalization, that are distinctly inferior to those of
dye (I).
Dye (I) may be applied to synthe-tic fibers9 and
partic~larly to synthetic polyamide fibers, by conventional
dyeing methods utilizing aqueous dispersions.
}lowever, for best applicational results as regards
equalization, a method is utilized which involves a firs-t stage
using a slightly alkaline medium. For this purpose it is
desirable to employ a system buffered with borates and phosphates
that permit the dyeing to start at a pH of about 8.5-9, which pH
is gradually reduced to a final slightly acid pH (5-5.5) by the
gradual addition of an organic acid according to known techniqueæ.
~or light shades it is preferable to complete the
dyei~g at a pH of about 6-6.5.
Dye ~I) is prepared by diaæotizing 2 cyano-5-chloro-
aniline with sodium nitrite and hydrochloric acid, followed by
coupling the resulting diazo compound in an acid medium with
N,N-diethyl meta~amino~succinyl-anilide~
The following examples will fur-ther illustrate the
invention. All parts and percentages are by weight, unless
otherwise indicated, and the relationship between parts by
weight and parts in volume corresponds to kg/liter.
~XAMP~E 1 ` ~ ~-
15.25 parts of 2-cyano-5-chloro-anili~e were treated
37r~7
~ith 220 par-ts of CM3COOH at 50~C for 15 minutes. This mass
was then cooled down to 0C with ice, and 30 r~ of HCl(d=1.18)
were added. Then under agitation, diazotization was effected by
slowly adding over a 30 minuteSperiod a solution of 6.9 parts
of NaN02 dissolved in 50 partsof H20. The diaæo suspension was
then poured o~er a period of one hour at O~G into a solution of
30 parts of the sodium salt of N~N-diethyl-m-amino-succinyl-
anilide, ~2 parts of sodium acetate crystals, and 500 parts of H20.
After about two hours of stirring at 0C, there were
added 30 parts by volume of (HCl d=1.18), then stirring was
effected for 30 minutes. The mass was then filtered and the
resulting precipitate was washed with H20 and then dried.
~ here was thus obtained 32~5 parts of a dye having
the following structure:
.. ~, .
CN
2H5
Cl NHCOCH2CH2-COOH
' ~ :'':
This dye was in the form of a red powder which, when applied `~ -
to polyamide fibers 7 resulted in a fast dyeing of a bright
red-scarlet color9 having an excellent equali~ation.
~XAMPLæ 2
0.5 part of the dye obtained in Example 1 was micron- -
ized in a ball mill and then dispersed in water. ~his dispersion
was added to a dyeing bath containing 1 g/l of a nonionic
surfactant ~oxyethylated castor oil, "E~ulson ~L", trademark of
Montedison) and a small amount o~ amonia and ammonium salt
(ammonium s~lfate) 90 as to obtain a pH of 8-~.5.
Dyeing was commenced on 100 parts of polyamide fabric
. . .
:~ .- : : . . . . . .
.
., ,.. . ,, . .:
'777
at 70C, and the temperature was gradually raised to the boiling
point. The fabric was then dyed for 30-~0 minutes at the boiling
temperature, and -then acetic acid was gradually added until a
final pll of 5.5-5 was obtained.
The dyed material was thoroughly rinsed in water and
then dried in hot air.
There was thus obtain a brilliant scarlet shade of
excellent equalization, endowed with good fastess to light and
stability to wet treatments.
Variations can, of course, be made without departing
from the spirit and scope of the invention.
Having thus described the invention, what is desired
to be secured by Letters Patent a~d hereby claimed is:
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..
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