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Патент USA US3050523

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3,050,516
United States Patent 0 " ice
1
2
3,150,516
water, and are white dischargeable. Viscose rayon, cot
ton and wool are comparatively well reserved by the dye
stu?s, especially when the goods are aftertreated with hy
MONOAZO DYESTUFFS 0]?‘ LOW SOLUBILHTY
IN WATER
Ernest Merian, Bottmingen, Otto Senn, Arlesheim, and
Walter Wehrli, Riehen, Switzerland, assignors to Sandoz
A.G., Basel, Switzerland
No Drawing. Filed Feb. 5, 1959, Ser. No. 791,277
Claims priority, application Switzerland Feb. 7, 1958
4 Claims. (Cl. 260—205)
drosul?tes. With those dyestuffs of the present inven
tion which possess sufficient a?‘inity for cellulose tri
acetate and polyester ?bers it is possible for the ?rst
time to produce on these ?bers bright orange shades
which are fast to light, pleating, sublimation, and heat
setting. The solution ofthis technical problem was im
10 portant above all in connection with brown mixtures.
This invention relates to new monoazo dyestuffs which
have low solubility in water and are of the general form
ula
Re
R4
Patented Aug. 21, 1962
CHz-Ri
|
|
R5
CHz-R2
Y
Certain of the new monoazo dyestuffs are also suitable
for coloring oils, lacquers and synthetic resins, and for
the dyeing of arti?cial ?bers in the mass.
The spun-dyed shades given by these dyestuffs in sec
15 ondary cellulose acetate and cellulose triacetate have
high fastness to light, washing, perspiration, gas fumes,
cross dyeing, alkaline bleaching, oxalic acid, dry clean
ing, and peroxide bleaching. Also, they show excellent
(I)
wherein
fastness to Water, sea water, soap baths, crocking, de
R1 stands for hydrogen, low molecular alkyl, low molecu
lar hydroxyalkyl, low molecular alkoxy alkyl, low
molecular acetoxyalkyl, low molecular propionyloxy
A great number of the amines which are employed
here in the form of their diazo compounds are new.
catizing, and pressing.
They are produced by the normal methods by the reac
tion of compounds of the formula
alkyl, or a radical of a carbamic acid alkyl ester,
R2 for low molecular acetoxyalkyl, low molecular
propionyloxyalkyl, low molecular cyanoalkyl or a
radical of a carbamic acid alkyl ester,
Re
Ira-02s
R3 for an amino group which may be mono- or disub
stituted,
R4 for hydrogen, halogen, methyl, ethyl, trifluoromethyl,
30
X
R,
R5
(IV)
i _ methoxy, ethoxy, or together with R5 for a -—CH=CH
wherein R3, R4, R5 and R6 possess the aforesaid mean
ings, with ammonia at high temperatures when X stands
for ?uoro, chloro, bromo or alkoxy, and by treatment
—CH:CH-— chain,
R5 for hydrogen, halogen, cyano, tri?uoromethyl, low
molecular alkylsulfonyl, a sulfonic acid amide group
which may be mono- or disubstituted, or together with
R, a --CH=OH—CH=CH- chain,
R8 for hydrogen or halogen, and a
Y for hydrogen, halogen, a low molecular alkyl or alkoxy
radical, the tri?uoromethyl or tri?uoroacetylamino
" of the compounds of Formula IV with hydrolysing agents
when X stands for an acylamino group.
A further process for the production of the primary
amines, some of which are new, consists in reacting 1
mol of a compound of the formula
radical, or an alkanoylamino radical with not more
than 18 carbon atoms.
R5
_
The process for the production of the new monoazo
dyestuffs of low water-solubility consists in combining 1
I
R4
mol of the diazo compound of an amine of the general
formula
_
(V)
wherein R4, and R5, and R6 possess the aforenamed
meanings and Z represents halogen, with ammonia, or
R0
|
33-028
|
R5
with a primary or secondary amine. This process of acid
NH;
it, 7 its
50 amide formation is carried out preferably in presence of
an acid-binding agent or with the aid of an excess of the
(II)
amine or ammonia which forms one of the reactants.
wherein R3, R4, R5 and R6 possess the aforecited mean
ings, with 1 mol of a compound of the formula
R5.and/or RFhalogen may also be introduced by di
rect halogenative processes of l-aminobenzene~4-sulfa
55 mides. The new products are isolated by one of the com
I
Y
\
mon basic operations, e.g. ?ltration, evaporation of the
solvent, salting out, precipitation from the solvent with a
suitable agent etc., where necessary after neutralization
of the hydrolysing solution.
CHi—R2
(III)
wherein R1, R2 and Y possess the aforecited meanings.
The diazo compounds are coupled with the coupling
components in an acid medium, which may be buffered.
A number of the new monoazo dyestuifs dye from
aqueous suspension polyamide ?bers (e.g. nylon, “Per
lon,” registered trademark), cellulose ester ?bers (eg.
secondary cellulose acetate, cellulose triacetate), poly
vinyl ?bers, polyacrylonitrile ?bers and polyester ?bers
(e.g. “Dacron,” “Terylene,” registered trademarks) in
60
The new intermediate products are also intended for
use in the production of pharmaceutical preparations.
In the following examples the parts and percentages
are by weight and the temperatures in degrees centigrade. ‘
The melting points are uncorrected.
Example 1: 22.2 parts of 1-arn-inonaphthalene-4-sulf
fonic'acid amide are dissolved in 200 parts of water and
32 parts of concentrated hydrochloric acid. After the
addition of 200 parts of ice the amine is diazotized by
dropwise addition of an aqueous solution of 7 parts of '
brilliant yellow, orange and scarlet shades. The dye 70 sodium nitrite. To the. resultant diazo solution is added
ings obtained with them possess very good fastness to
a solution of 20.4 parts of 1-(N-cyanoethyl-N-hydroxy
light, gas fumes, washing, perspiration, water and sea
ethyl)-amino-3~methylbenzene in 50 parts of water, 50
3,050,516
3
4
parts of ice and 13 parts of concentrated hydrochloric
somewhat more reddish shade are obtained which in part
show better fastness to washing.
acid. Coupling takes place instantaneously. The new
dyestuif which has the formula
Example 10: When the 100 parts of methylamine in the
?rst paragraph of Example 2 are replaced by 140 parts of
CHz-CHz- O H
dimethyla-mine, the intermediate product obtained is l
acetylaminonaphthalene-4-sulfonic acid dimethylamide
with a melting point in the crude state at 200—204°. It
can be hydrolysed in a similar manner to give l-amino
(SE,
naphthalene-4-sulfonic acid dimethylamide of the formula
is subsequently ?ltered off, washed free of acid, and dried. 10
It dissolves in organic solvents with an orange coloration
and in concentrated sulfuric acid with a red-violet color
ation. Applied from aqueous dispersion, it dyes cellulose
acetate and nylon in bright, level orange shades. The
dyeings have good fastness to light, gas fumes, perspira 15
tion, sea water, sublimation, and pleating, and are readily
dischargeable.
The corresponding dyestuif (Example 2) obtained from
N-cyanoethyl-N-hydroxyethylaminobenzene also dissolves
NH]
When the diazo compound obtained from this is combined
in a similar way with 1-(N-hydroxyethyl-N-cyanoethyl)
amino-3-methylbenzene, an orange disperse dyestuif is
obtained which has similar fastness properties and dis
in concentrated sulfuric acid to give red-violet solutions,
and the dyeings produced with it on cellulose acetate and
nylon possess similar fastness properties. On polyester
?bers, however, it has a slightly more yellowish shade.
solves in concentrated sulfuric acid with a red-violet colo
ration.
By using in place of the aforementioned diazo com
pound one from l-aminonaphthalene-4-sulfonic acid-N
Example 3: 287 parts of l-acetylaminonaphthalene-4
sulfonic acid are added to 833 parts of chlorosulfonic 25 methyl~N~phenylamide (Example 11) or l-aminonaph
thalene-4-sulfonic acid-N-(Zt-hydroxy)aethyl-N-phenyl
acid at 10—20°. The solution is stirred for 2 hours at
amide (Example 12) dyestuffs of very good solubility in
20° and then heated to 50°. After 16 hours at this
acetone are obtained which are suitable for the dope
temperature the reaction mass is run into a mixture of
8000 parts of ice and 1000 parts of water, upon which
1-acetylaminonaphthalene-4-sulfonic acid chloride pre
dyeing of secondary cellulose acetate and cellulose triacet
30 tate.
Example 13: 23.45 parts of l-amino-Z-chlorobenzene
cipitates. This is isolated by ?ltration and Washed free
of acid. The moist press cake obtained is mixed at room
temperature with 500 parts of Water, 500 parts of ice
and 100 parts of methylamine. After 16 hours the tem
perature is gradually increased to 50°. Stirring is con
tinued for 16 hours at the same temperature and after
4-sulfonic acid dimethylamide are aded to 130 parts of
concentrated sulfuric acid at 60°. In the course of 1
hour 7 parts of solid sodium nitrite are added to the
solution. The reaction mass is stirred for 1 hour at 60'i
and then run into a mixture of 500 parts of ice and 200
parts of water. if a slight excess of nitrous acid is
present it is destroyed by an addition of 0.5 part of
amidosulfonic acid. To the diazo solution obtained are
this time the precipitated l-acetylaminonaphthalene-Ll
sulfonic acid methylamide, which melts at 221-225" in
the crude state, is ?ltered off, washed free of alkali, and
added 18 parts of N-ethyl-N-cyanoethylaminobenzene
(3.13.01 115°). Formation of the dyestuif takes place
immediately. The dyestuff paste is ?ltered off, the residue
dried. 27.8 parts of the acetyl compound so formed are
added to 200 parts of Water and 32 parts of concen
trated hydrochloric acid and saponi?ed by boiling for 6
Washed free of acid, and dried.
responds to the formula
hours. The new intermediate product obtained in hydro
chloric acid solution has the formula
The new dyestuff cor
01
CH3\
I
/C2H5
CH3
50
It is diazotized as described in Example 1 and the diazo
compound is added to N-hydroxyethyl-N-cyanoethylrnino—
benzene. The new dyestuif formed dissolves in organic
CHz- C H2- 0 N
(Melting point 160-161")
It dyes secondary cellulose acetate and cellulose tri
acetate, polyamide ?bers and polyester ?bers in brilliant ‘
solvents and in 1% sodium hydroxide with an orange
orange shades of high tinctorial strength which have good
coloration, and in concentrated sulfuric acid with a red 55 fastness to light and excellent fastness to washing, per
violet coloration.
spiration, sea water, gas fumes, sublimation, pleating and
It is applied to cellulose acetate ?bers and polyamide
cross dyeing. The dyeings are dischargeable with ease
?bers from ‘aqueous suspension at high temperature,
and the dyestutf reserves viscose rayon and cotton satis
preferably in presence of compounds with dispersing
factorily; the wool reserve too is fairly good and can be
action, to give brilliant yellow-orange shades which show 60 improved by suitable aftertreatment, e.g. with hydro
good fastness to light, gas fumes, sublimation, and wet
sul?te.
treatments. The dyeings are readily dischargeable.
A dyebath is prepared with 1 part of the above-de
When in place of N-hydroxyethyl-N-cyanoethylamino
scribed dyestuff dispersed with the aid of Turkey red
benzene aliquot amounts of N-ethyl—N-cyanoethylamino
oil, 6 parts of a sulfonated fatty alcohol and 3000 parts
benzene (Example 4) or 1-(N-hydroxyethyl-N-cyano
of water. 100 parts of secondary cellulose acetate fabric
ethyl)-amino-3-methyl-benzene (Example 5) are employ
.ed, similar dyestuffs are obtained which exhibit virtually
the same light fastness.
On the other hand, by using as coupling components
the ethylcarbamic ester of l-(N-ethyl-N-hydroxyethyl
amino-3-methylbenzene (Example 6), 1-N,N-di-(-acetoxy
ethyl)-amino-3-acetylaminobenzene (Example 7), l-N,
are entered at room temperature.
The temperature of
the dyebath is increased to 80° in 1 hour and this tem
perature maintained for a further hour. After this time
the dyeing process is completed. The dyed fabric is
removed, rinsed and dried.
Similar dyeing properties are possessed by the follow
ing dyestuffs which are produced in an analogous manner:
Example 14: 4-(N-methyl -N -cyanoethyl)-amino-2'
benzene (Example 8) or l-N,N-di-(ace-toxyethyl)-amino
chloroazobenzene-4’—sulfonic
acid amide, MP. l74—l75°_
3-propionylaminobenzene (Example 9), dyestuffs of a 75 Example 15: 4-(N-methyl - N - cyanoethyl)-amino-2’
N - di - (acetoxyethyl) - amino-3-acetylaminor6-methoxy
3,050,516
5
E
chloroazobenzene - 4’ - sulfonic acid methylamide, M.P.
153-155 ° .
Example 40: 4~(N-acetoxyethyl - N ' cyanoethyD-ami
110-2’.5'-d1ChlOI‘0aZOlb<-)31Z611€—4'~Sl1lf0I11C acid methylamide,
Example 16: 4-(N-methyl - N - cyanoethyl)-amino-2'-
‘M.P. 160-163".
chloroazobenzene-4'~sulfonic acid dimethylamide, M.P.
148-149”.
V
Example 41: 4-(N-rnethyl - N - cyanoethyD-amino
5
‘Example 17: 4-(N-ethyl - N - cyanoethy1)-amino-2'-
Example 20: 4'-(N-propyl - N - cyanoethyl)-amino-2’-
v
ide, M.P. 110-112°.
10-
chloroazobenZene-4’asulfonic acid amide, M.P. 171-172".
acid-2”-hydroxyeth~
Example 42: 4-(N-ethyl - N - cyanoethyl)-amino-2'.5'
dichloroazobenzene-ll'-sulfonic acid-2"-hydroxyethylam
chlor-oazobenzene-4’-sulfonic ‘acid methylarnide, M.P.
Example 19: 4-(N-propyl - N - cyanoethyl)~amino-2’-
2'.5'-dichloroazobenzene-4’-sulfonic
ylamide, M.P. 170-171".
chloroazobenzene-4’-sulfonic ‘acid amide, M.P. 167-169”.
Example 18: 4-(N-ethyl - N - cyanoethyl)-amino-2’136-138".
-
Example 43: 4~(N-propyl - N - cyanoethyD-amino
2’.5'-dichloroazo<benzene-4'-sulfonic acid-2"-hyd=roxyeth
ylamide, M.P. 118-l2(}°.
The dyestuif 4-(N-ethyl - N - cyanoet'hyl)-amino-6’
chloroazo-benzene-4’esulfonic acid methylamide, M.P.
chloro-l,1’-azobenzene-2’.4’-di(sulfonic acid methylam
144-146”.
15 ide) (Example 44) vwith melting point at 170° has a
Example 21: 4-(N-butyl - N - cyanoethyl)—arnino-2’-
somewhat yellower and duller shade, but shows equally
chloroazobenzene~4'-sulfonic acid amide, M.P. 145-147°.
good a?inity for secondary cellulose acetate and gives
Example 22: 4—(-N-butyl - N - cyanoethyl)-amino-2’-
chloroazobenzene-4’-sulfonic acid methylamide, M.P.
126-129".
.
Example 23: 4-(Nabutyl - N - cy-anoethyl)-amino-2’-
dyeings with good fastness properties.
Dyestuffs which are substituted in the 2'-position by
20 hydrogen, e.g. Example 45:
Hag
chloroazobenzene-4'~sulfonic acid dimethylamide, M.P.
02m
\
134-135".
/N“S°
Example 24: 4~(N-acetoxyethyl - N - cyanoethyl)-
_
Ni)‘
/
N\
H30
CHrCHrCN
ami1'10-2'-°h10f0aZ0b6I1Z6I1e-4'-S111f0ni<> acid amide, M.P- 25 dye secondary cellulose acetate, cellulose triacetate, poly
162-164".
amide ?bers and polyester ?bers in fast yellow shades.
Example 253 4"(N"a¢el0XYelhY1 — N - cyanoethynamrho-2'-chloroazobenzene-4’-sulfonic acid methylamide,
M.P. 130-131".
Further dyestuffs possessing similar fastness properties
are
Example 46: 4-(N-acetoxyethyl-N-cyanoethyl)-amino
EXEIDPIB 26? 4-(N-acet0XYethY1 - N - CYaIIOBthYU-ami- 3O aZobenzene-4'-sulfonic acid methylamide, M.P. 152-154°.
no-2’-chloroazobenzene-4’-sulfonic acid dimethylamide,
M.P. 139-140°.
Example 47: 4-(N-acetoxyethyl-N-cyanoethyl)-amino
azobenzene-4'-sulfonic acid dimethylamide, M.P. 122
Similar dyestu?ls are obtained when the sulfonic acid
125°.
gdirnethylamide group in Example 4 is replaced by a SulDyestu?’s analogous to Example 13 are obtained from
ionic acid ethylamide group‘ (Example 27), a sulfonic 35 l-amino-Z-bromobenzene-4-sulfonic acid methyl- (Ex
acid iso~propylamide (Example 28), 1a sulfonic acid hyample 48), ethyl- (Example 49), or propylarnide (Exam
droxyethylamide group (Example 29) or a sulfonic acid
ple 50). Particularly good washing fastness is shown
methoxypropyl amide group (Example 30).
by the dyestuffs
2'5'—dichloroazobenzene-4’-sulfonic acid methylamide,
and Example 52:
M.P. 202-20‘3°.
which dye cellulose acetate ?bers and polyamide from
Example 321 4~(N-BihY1 - N - cYElI105thY1)-aminO-2'-5’- '
aqueous dyebaths in red-orange shades.
dichloroazobenzene-4’-sulfonic acid methylamide, M.P. 55 The dyestuif 4’-(N-ethyl-N-cyanoethyl)-amin0_2,.t1-i_
220-222°.
?uoromethyl-l-l’-azobenzene-4-sulfonic acid methylamide
Example 331 4-(N-pr0pyl - N - cy-anoethyn-?mino-
(Example 53) possesses similar dyeing properties, while
2’.5’-dichloroazobenzene-4'-sulfonic acid methylamide,
the yellower dyestu? 4’-(N-acetoxyethyl-N-cyanoethyl)_
M.P. 136-137”.
amino-Z-‘tri?uoromethyl-l.1’-azobenzene-4-sulfonic acid
_EX3II1P1e 34¢ 4-(N-bllt‘ll -
'
-¢yan°6thy1)-E1I1}in0-2'-5'- 60 N-methyl-phenylamide (Example 54) is more suitable
dichloroazobenzene-4'-sulfon1c acid methyl amide, M.P.
for the dyeing of ?bers, plastic Sheet and lacquers (3f
157-160 -
cellulose acetate in the mass.
_
Example 35: 4“('N‘methyl ‘ N ‘ cyanoethyn'ammo‘
Disperse dyestuffs of redder shade with very good fast
%;gifggilor°aZ°benZene'4"su1f°ni° acid amide’ M‘P'
ness properties are the compounds 4'~(N-acetoxyethyl-N
Exampl‘e 36: 4_(N_ethy1 _ N _ cyanoethylyan?noacst 65 cyanoethyl) - amino-Z-cyano-l.1’-azobenzene-4—su1fonic
dichloroazobenzene-4’-sulfonic acid amide, M.P. 190°.
Example 37: 4_(N_propyl _ N _ cyanoethyl)_amino_
acid methylamide (Exflmple 55)’ 4"(N'methyl' or 'ethyl'
N icyanoethyl) - amino — 2-cyano-1.l’-azobenzene-4-sul
2’.5’-dichlorozabenzene-4’-su1fonic acid amide, M.P. 168-
fomc acid methyl amlde (Examples 56+57) and 4"biS'
170.,‘
(N-acetoxyethyl)-amino-2'-acetylamino- or -tri?uoroacet—
‘
Example 38: 4-(N-butyl - N - cyanoethyl)-amino-2'.5’- 70 Ylamino' 0F -Pf0Pi011ylamiI10-2-cyauo-l,1"~azobenzene-4
dichloroazobenzene>4’~sulfonic acid amide, M.P. 156159=>_
Example 39; 4-(N-acetoxyethyl - N - cyangethyn-ami-
no-2’.5’-dichloroazobenzene—4’-sulfonic acid amide, M.P.
159-162“.
Sulfonic acid dimethylamide (Examples 5840)
In the following table further monoazo dyestuffs are
recited which may be produced in an analogous manner
as described in the foregoing examples. They correspond
75 to the general Formula I.
3,050,516
1‘ Examples 88 and 89: By using in place of the diazo
compound named in Example 13 one of 1-amino-2.5-di-
machine and spun to give orange ?laments. The dye
ings are characterized by very good fastnessto light, Wash
chlorobenzene-4-sulfonic acid-N-methyl-N-phenylamide
ing, cross dyeing, chlorine, oxalic acid,‘ peroxide, sub
or 1-arnino-2.5-dichlorobenzene-4-sulfonic acid-N-(2'-hylimation, bleaching, gas fumes and dry cleaning, and are
droxy)-ethyl-N-phenylamide, dyestuffs are obtained 35 considerably stable to hydrosul?te. Similar properties
which have very good solubility in acetone and are.
are possessed by the dyestuff Example 92.
suitable for the dyeing of cellulose acetate ?bers in the
mass.
The latter dyesituff however has a much more yellowish
_ shade in spun-dyed acetate than the above-mentioned dye
Dyeings of particularly good fastness to gas fumes and
chlorine are obtained when the dyestuff Example 90‘:
or the dyestulf Example 91:
stuffs.
The dyestuffs 4’-(N-methyl- or -ethyl— or -acetoxyethy1l
55 Nucyanoethyl) - amino - 2 - cyano - 1.1’ - azobenzene
are dissolved in acetone together with cellulose acetate
4 - sulfonic acid - N - methyl - N - phenylamide- or -N
and the orange-colored mass spun in the normal way by
ethyl-N-phenylamide or -N-cyclc~hexylamide (Examples
the dry spinning process.
93461), 4’ - ibis - (N
The spun dyeing method is as follows:
-acetoxyethyl) - amino - 2'
65 dccanoylamino - 2 - cyano - 1.1’ - azobenzene - 4 - sul
100 parts of secondary cellulose acetate are dissolved
in_ 300 parts of a mixture of solvents consisting of 93%
fonic acid dimethylamide (Example 102) and the his
phenylcarbamic acid ester of 4’-di-(2"-hydroxy)-ethyl
of acetone and 7% of methanol.
amino - 2' - chloro - 2 - cyano - 1.1’ - azobenzene - 4 - sul
The mass is mixed for
a short time and left overnight to swell. 1 part of the
fon-ic acid dimethylamide (Example 103) are suitable for
monoazo dyestuff obtained according to the above example 70 producing fast, brilliant red-orange to scarlet shades in the
is dissolved in 60 parts of the same mixture of solvents
mass.
‘by simple shaking. This solution is ‘added :to the celluIn the following table vfurther monoazo dyestu?is are
lose acetate solution and the whole is mixed in an open
recited which may be produced in ‘an analogous manner
vessel until 60 pamts of the solvent mixture have evapas described in the foregoing examples and which are
orated. The dyed mass is pumped into the spinning 75 suitable for dyeing cellulose diacetate and triacetate ?
3,050,516
bers in the mess. They correspond to the formula
Ra
/CHz—CHz-—O—C 0-R7
Rs-OzS
|
ii
R4
N=N—<:>~N\ CHrCHz—-O—C O~R7
1.
Y
Examples
R3
R4
(VI)
R5
Ru
R1
Y
Color
N(G4Hq)=
N (C4H9)2
01
H
H
SO:—N (0411a):
01
H
02115
NH-CaHs
01
C1
Orange.
D0.
(0113»
H
ON 7
H
NH-G¢Hn
C1
Scarlet.
H
H
H
H
H
01
01
Cl
H
H
ocgH?
C1
131~
01
01
Cl
01
H
H
H
H
H
H
H
H
01
01
01
H
H
1
01
Br
H
H
N H-CaHa
NH-GQH5
NH~C5H5
NH—COH5
NH-CBHS
NEE-00H,
2H5
NH~CGH5
NH—OBH5
NH—-CsH17
NH-Calih
NH-C?lih
NH-OGEs
NH-C6H4~OH3
NH-O5H4-OH;
O1
01
01
B1‘
C1
01
NH-CO-CaH';
NH-—OO-—C9H1v
NH-—-CO—-—C11Ha5
O1
C1
01
01
C1
01
Orange.
Do.
D0.
D0.
D0.
Do.
Scarlet.
Do.
Do.
Orange
D0.
Do
Do.
D0.
Do.
N (C4H9)2
4119):
N(O4H§)_O6H5
N (CqH5)—CHz—OHr-CN
NH——OH2——CHz-CHr-O——OH;
NH-—CHz—OHa—0—-OHg-OH:
NH-CaHs
NH~O5H5
N(G3H7)—OoH5
N(CHa)z
NH-Odilg
N(CH2——OHr—OH)g
M01115),
N (cm),
N(C4Ho)a
- N(GH3)2
NH-eCaHu
H
H
SOPCHE_OH=CHQ
H
C1
Br
01
ON
H
Soy-CH5
Bl‘
NH—~C7H5
C1
D0.
H
S0a-—NH—~C&HU
H
NH~—C10H7
C1
D0.
Formulae of representative dyestuffs of the foregoing
examples are as follows.
Example 16_
Having thus disclosed the invention what We claim is:
1. A monoazo dyestuff having low solubility in water,
the formula of which is
01
O1
30
H10\/NQO’SO‘N=NGN\
1
/CH3
\
H30
R<
l
'/lower alkyl
/N-so,O~N=NC>-N\ CHTCHTON
1W“ 811*“
CHTCHHW
Example 18:
wherein R3’ is a member ‘selected from [the ‘group con
35 sisting of hydrogen and lower alkyl.
01
2. The m'onoazo dyestuff cor-responding to the formula
]
/
GET-CH3
Cl
I-IHC-HN-OHGmNGN
Hs0\
I
/0H3
\CHQ-CHz-CN
4O
/N—0zS<:>—N=N<:>N\
Example 22:
Hi0
GHrCHrCN
(In
HaC-HN-OgS
4N: -
y s
o1
N\
'
CHz-CH:
45 HaC—HN—OzSON=NC>~N/\
CHrOH5-CH2-OE3
CHa-CHa-CN
4. The monoazo dyestuif cor-responding to the formula
Example 47:
CHa-CHz-CN
CHa-CHa-O—O O—CHa
/
HaC
HBO
' w
t ,
spondmc,
to the formula
I
CHrCm-CN
Example 34:
C1
3. The monoazo d e~tuff corre ‘
CHTCHTOHrOHZ
/
,
References Cited in the ?le of this patent
UNITED STATES PATENTS
1,975,160
2,082,156
2,109,024
Jordan et a1 _____________ __ Oct. 2, 1934
Felix et a1. ___________ .... June 1, 1937
Holzachet a1 ___________ __ Feb. 22, 1938
2,782,186
Merian ..
2,891,942
Merian ____________ .._ June 23, 1959
__________ __ Feb. 19, 1957
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