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Патент USA US3096332

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'ic
U ‘ted Stts
?atented July 2, 1963
0
1
£1
2-naphthol-3-carboxarnide, commonly referred to as
Naphthol AS compounds, is preferred. Representative
3,096,322
aminobenzenesulfonamide and ,B-naphtlrol compounds ‘are
disclosed herein-after. R1 may be, for example, a methyl,
AMINOBENZENESULFONAIVHDE AZO DYES FOR
ACRYLIC FIBERS
James M. Straley and Raymond C. Harris, Kingsport,
Tenrn, assignors to Eastman Kodak Company, Roch
ester, N.Y., a corporation of New Jersey
N0 Drawing. Filed Mar. 14, 1960, Ser. No. 14,560
6 Claims. (Cl. Mil-2&4)
an ethyl, a propyl or a butyl radical.
3-amino-4-methoxy-N-?-dimethylaminoethylbenzenesul
fonamide,
3-amino-4-methoxy-N-B-diethylaminoethylb enzenesul
This invention relates to new :azo compounds and their 10
application to the art of dyeing or coloring acrylic ?bers.
fonamide,
3-amino-4-methoxy-N-B-di(n-propyl) aminoethylben
zensulfonamide,
The invention also relates to the new aminobenzenesul
fonamide compounds used in preparing the new azo corn
3-amino-4-methoxy-N-[3-di (n-butyl) aminoethylhenzene
pounds of the invention and to their preparation.
As well known, polyacrylonitrile ?bers are di?‘icult to 15
dye and their dyeing has presented problems. The poly
3-amino-4-rnethoxy-N-y~dimethylaminopropylbenzene
acrylonitrile ?bers commercially available usually contain
sulfonamide,
sulfonamide,
3amino-4-methoXy-N-v-diethylaminopropylbenzenesul
fonamide,
over 85% polyacrylonitrile and few of the dyes offered for
3 -amino-4-rnethoxy-N-~/-di ( n-p'ropyl) amincpropylib en
sale show a?inity therefor. Thus, for example, the usual
zenesulfonamide,
I
cellulose acetate disperse dyes have little or no a?lnity 20 3~amino-4~methoXy-N-~/-di (n-butyl) aminopropyl‘benzene
for polyacrylonitrile ?bers.
sulfonamide,
'It is an object of the invention to provide new 'azo dye
stuffs. Another object is to provide new azo dyestu?s
3-amino-4-meth0xy-N-B-m orpholinylethylbenzenesul
having ai?inity for polyacrylonitrile ?bers. A further
object is to provide dyed polyacrylonitrile materials hav 25
ing good fastness to light, gas, washing, and sublimation.
3-amino-4-methoXy-N-v-morpholinylpropylbenzenesul
Another object is to pnovide new aminobenzenesul
fonamide compound. A further object is to provide a
satisfactory process for preparing the new azo and the
new :aminobenzenesulfonamide compounds of the inven 30
tion.
The new azo compounds of the invention have the
formula:
(In:
35
fonamide,
.
fonamide,
3-amino-4-methoxy-N-[B-piperidylethylbenzenesulfon
amide,
3amino-4-methoxy-N“yapiperidylpropylbenzenesulfon
amide,
3-amino-4¢ethoiiy-N-B~dimethylaminoethylbenzenesulfon
amide,
3amino-4-ethoxy-N-'y-dimethylaminopropylbenzénesul
fonamide,
3 -amin o-4-methoxy-N-?- (methyl ,ethyl) aminoethyl-ben
zenesulfonamide and
3-arnino-4-methoxy-N-q- (methyl,ethyl ) aminopnopy-lben
zenesulfonarnide
~
.
are representative of the aminobenzenesulfonamide com
pounds used in preparing the newazo compounds of the
H
SOzNRN (R1):
invention. The aminobenzenesulfonarnide compounds
wherein X represents a member selected from the group
are believed to be new and their prepanation is described
consisting of a methyl radical ‘and an ethyl radical, R
herein.
represents an alkylelne radical having 2 to 3 carbon atoms,
p-Na-phthol, 6-bromo-2-hydroxynaphthalene, 3-inc
45
R1 represents an alkyl radical having 1 to 4 carbon atoms,
thoxy-Z-hydroXynaPhthaIene, 2-hydroxynaphthalene-7-‘~
N(R1)2 collectively represents a member selected from the
sulfonamide, Z-hydroxy-S-naphthoic anilide (Naphthol
group consisting of the morpholinyl radical and the
piperidyl radical and Q represents a ?-naphthol radical
devoid of a Water-solubilizing group. They dye acrylic
AS), 2-hydr0Xy-3-naphtlioic-o-toluidide (Naphthol ASD),
2 - hydroxy - 3qnaphthoic-p-toluidide,
?bers, such ‘as Verel and Orion 42, red, orange and scarlet 50
shades, for example, having good fastness to light, gas,
washing, and sublimation.
2-hydroXy-3-naph
thoic-o-anisidide (Naphthol ASOL), 2-hydroxy-3-rraph
thoic - p - anisidide, 2-hydr-oxy-3-naphthoic-m-nitranilide
(Naphthol ASBS) , 2 - hydroxy — 3 - naphthoic-p-chloro
anilide, 2-hydroxy-3naphthoic-o-phenetidide (Naphthol
The new azo compounds of the invention "are prepared
ASPN), 2-hydroxy-3-naphthoic-p-ethoxyanilide, the 2,4
by diazotizing :an aminobenzenesul-fonamide compound
dimethoxy-5-chloroanilide of 2-hy-droxy-3-naphthoic acid,
55 the 2,5-dimethoxyanilide of 2-hydroxy-3-naphthoic acid,
having the formula:
the 2-methyl-4-chloroanilide of 2-hydroXy-3-naphthoic
acid, the 2,5-dimethoxy-4-chloroanilide of 2-hydroxy-34
naphthoic acid, the 2,4-dimeth0Xy-5-bromoanilide of 2
60
I
H
SOzNRN (R1):
wherein X, R, R1 and N(R1)2 have the meaning previ
hydroxy-3-n-aphthoic acid, the 2,5-dimethoxy-4-bromo
anilide of 2-hydroXy-3-naphthoic acid, the 2,5-diethoxy
4~chloroanilide of 2-hydroXy-3-naphthoic acid, the 2,5
idiethoxyanilide of 2-hydroxy-3-naphthoic acid, the 2,5
dimethoxy-4-chloroanili-de of 6-bromo-2-hydroxy-3-naph
thoic acid, the 2,4-dimethoxy-5-chlordanilide of 6-bronio—
ously assigned to them and coupling the diazonium com 65
2-hydroxy-3-naphthoic acid, the 2,4-dim'ethoXy-5-chloro-'
pound obtained with a ,B-naphthol compound which is
anilide of 6-rnethoxy-2-hydroxy-3-naphtlioic acid, 2-hy-‘
devoid of a Water-‘solubilizing group. The aminoben
z'enesulfonamide compounds are new compounds. Their
preparation is described hereinafter.
While any p-naphthol compound which is devoid of
a water-solubilizing group and which is capable of
coupling can be employed the use of N-aryl derivatives of
dnoxy - 3 - naphthoic - a - naphthylamide and 2-hydroxy-34
naphthoic-B-naphthylamide (Naphthol ASSW) are illus
trative of the B-naphthol coupling components used in
preparing the azo compounds of the invention. ' ‘
The following examples illustrate the invention.
3,096,322
3
Example 1
20 grams of 3-amino-4»methoxy-N-wdimethylarnino
propylbenzenesulfonamide were dissolved in 35 cc. of con
centrated hydrochloric acid and 135 cc. of water and the
temperature was brought to" 0° C. A solution of 5.55
grams of sodium nitrite in 10 cc. of water was added, with
stirring, at a temperature below 5° C. and the resultmg
4
red shades having excellent fastness to light, gas, wash
ing and sublimation.
Example 4
23.9 grams of 3-amino-4-ethoxy-N-?-piperidylethylben
zenesulionarnide were diazotized and the diazonium com
pound obtained was coupled with 21 grams of the p
anisidide of 2-hydroxy-3~naphthoic acid. Diazotization,
solution was kept at a temperature below 10° C. for 1.5
hours while stirring. The excess nitrous acid was
coupling and recovery of the dye compound formed were
‘carried out in accordance with the procedure described
10 in Example 1. The dye compound obtained colors textile
destroyed with sulfamic acid.
_
25 grains of the 2,4-dimethoxy-5-chloroanil1de of 2
materials made of Verel and Orlon acrylic ?bers red
hydroxy-3-naphthoic acid were dissolved in 350 cc. of
shades having excellent fastness to light, gas, washing and
water containing 21 cc. of a 20% aqueous sodium hy
droxide solution by good stirring.
sublimation.
’
-
Example 5
3.63 grams of 3-acetamino-4-methoxy-N-v-dimethyl
1.5 grams of a detergent and wetting agent, such as 15
Igepon T [C17H33'CO'N(CH3) -C2H4-SO‘3Na] in 140 cc.
aminopropylbenzenesulfonamide were added to 50 cc. of
of water were ‘added. The volume was brought to 2,450
concentrated hydrochloric acid and 100 cc. of water, and
cc. by the addition of chipped ice, and the mixture was
the resulting mixture was re?uxed for 2 hours. The re
cooled to 0° C. 16 cc. of glacial ‘acetic acid were added
sulting
solution was cooled to 0° C. and the 3-amino-4
‘all at once with e?icient stirring after which the diazo
solution prepared as described above was added while
methoxy-N - 'y - dimethylaminopropylbenzenesulfonamide
present therein was diazotized by the addition of 0.72
maintaining the temperature of the reaction mixture below
gram of sodium nitrite in 10 cc. of water. Diazotization
10° C. Upon completion of the coupling reaction which
was carried out at a temperature below 5 ° C. for 1.5 hours
takes place the mineral acid present was made neutral to
Congo red paper by the addition of sodium acetate and 25 while stirring. The diazo solution thus prepared was
run into a solution of 2.71 grams of 6-bromo-2-hydroxy
the product which precipitated was recovered by ?ltra
naphthalene
in 100 cc. of 3% NaOH containing 100
tion, washed well with water and ‘air-dried. The dye com
grams
of
cracked
ice. Upon completion of the coupling
pound thus obtained has the formula:
reaction which takes place the mineral acid present was
30 made neutral to Congo red paper by the addition of
sodium carbonate and the dye compound which precipi
tated was recovered by ?ltration, washed well with water
and dried. The dye compound obtained dyes textile mate
rials made of Verel and Orlon acrylic ?bers red shades
having excellent fastness to light, gas, washing and sub
‘ do
limation.
Example 6
Example 5 was repeated using 2.63 grams of the :anilide
It dyes textile materials made of Verel and Orlon acrylic
?bers red shades having excellent fastuess to light, gas,
washing and sublimation.
tained dyes textile materials made of Verel and Orion
Example 2
acrylic ?bers bright red shades having excellent fastness
to light, gas, washing and sublimation.
20 grams of 3-amino~4-methoxy-N-'y-dimethylamino
propylbenzenesulfonamide. were dissolved in 35 cc. of
concentrated hydrochloric acid and 135 cc. of water and
the temperature was brought to 0° C. A solution of
5.55 grams of sodium nitrite in 10 cc. of water was added,
with stirring, at a temperature below 5° C. and the re
sulting solution was kept at a temperature below 10° C.
for 1.5 hours while stirring. The excess nitrous 'acid was
destroyed with sulfamic acid.
, A coupler solution was prepared by dissolving 12.5
grams of the sodium salt of ?-naphthol in 5 00 cc. of Water
and then bringing the volume to 1500 cc. by the addition
of ice. The diazo solution prepared as described above
was added to the coupler solution at a temperature below
of 2-hydroxy-3-naphthoic acid as the coupler instead of
6~bromo-2-hydroxynaphthalene. The dye compound ob
Example 7
3.7 grams of 3-acetamino~4-methoxy-N-,B-diethylamino
ethylbenzenesulfonamide were diazotized and the diazo
nium compound obtained was co pled with 1.74 grams of
3-rnethoxy-2-hydroxynaphthalene.
Diazotization, cou
phng and recovery of the dye compound formed were
carried out in accordance with the procedure set forth
in Example 5. The dye compound obtained dyes textile
materials made of Verel land Orlon acrylic ?bers bright
red shades having excellent fastness to light, gas, Wash
ing ‘and sublimation.
Example 8
10° C. with good stirring. The mineral acid present was
3.5 grams of 3-acetamino-4-ethoxy-N-/3-dimethylan1ino
made neutral to Congo red paper by the addition of
ethylbenzenesulfonamide
were diazotized and the diazo
sodium acetate and the product which precipitated was 60 nium compound obtained was coupled with 2.3 grams of
recovered by ?ltration, washed well with water and air
2-hydroxynaplithalene-7-sulfonamide. Diazotization,cou
dried. The dye compound obtained dyes textile mate
pling and recovery of the dye compound formed were
rials made of Verel and Orlon acrylic ?bers bright orange
carried out in accordance with the procedure set forth
shades which have excellent fastness to light, gas, wash
in Example 5. The ‘dye compound obtained dyes textile
65
ing ‘and sublimation.
materials made of Verel and Orlon acrylic ?bers scarlet
Example 3
‘20.7 grams of 3-amino-4-methoxy-N-?-diethylamino
ethylbenzenesulfonamide was diazotized and the them
nium compound obtained was coupled with 19.4 grams of
the o-toluidide of 2-hydroxynaphthoic ‘acid. Diazotiza
tion, coupling and recovery of the dye compound formed
were carried out in accordance with the procedure de
shades having excellent .?astness to light, gas, washing and
sublimation.
The following tabulation further illustrates the azo
compounds of the invention together with the color they
produce on polyacrylonitn'le textile materials, such as
those made, for example, r‘rom Verel or Orlon acrylic
?bers. The azo compounds indicated below are prepared
by diazotizing the amines listed under the heading
scribed in Example 1. The dye compound obtained colors
textilematerials made of Verel and Orlon acrylic ?bers 75 “Amine” and coupling the diazonium ‘compounds ob
tained with the compounds speci?ed in the column en
5,090,322
6
amine v-dimethylaminopropylamine, v-diethylaminopro
pylamine, »y-di-n-propyl-aminopropylamine, 'y-di-n-butyl
titled “Coupling Component.” The diazotization, cou
pling and recovery operations are carried out in accord
ance with the procedure described in Example 1.
aminopropylamine
(1'1~C4H9) 2]
5
Amine
Coupling Component
3-amino-4-methoxy-N-7dimethylaminopropyl-
2-hydroxy-3-naphtholc
anilide.
{i - piperidylethylarnine, 'y - piperidylpropylamine, ,8 - mor
Color
pholinylethylamine, 'y-morpholinylpropylamme
Ha Ha
red.
benzenesulfonamide.
Do ________________________ __ 2-hydroxy-3~naphthoic
D0.
10
o—anisidide.
Do ________________________ __
2-hydroxyV-3-naphthoic
Do ________________________ __
2-hydroxy-3-naphthoic
p~toluidide.
D0.
.
Do.
Do ________________________ __ 2-hydroxy-3-naphthoic-
Do.
Do ________________________ ._
(2’-methyl-4’-ehlorc)
anilide.
3-amin0-4-1nethoxy-N-?
2-hydroxy-3-naphthoie-
piperidylbenzenesul-
?-methylethylaminoethyl amine
Do.
p-ehloroanilide.
2-hydroxy-3-naphthoico-phenetidide.
15
Do.
and 'y-methylethylaminopropylamine
anilide.
fonamide.
Do ________________________ __
6‘bromo-2-hydroxy-
naphthalene.
2-hydroxy-3-naphthoie
anilide.
3-aminc-4-methoxy-N-Bmorpholinylbenzenesul-
orange.
red.
20
fonamide.
Do ________________________ __
?-naphthol ________________ __
3-amino-4-meth0xy-N-7
dimethylaminopropyl-
are illustrative of the amine compounds having the For
D0.
2-hydroxy-3-naphthoieo-toluidide.
D0.
Do ________________________ __ 2-hydroxy-3-naphthoic-
D0.
mula D.
benzenesulfonamide.
a-naphthylamide.
3-amino-4-ethoxy-N-B-
2-hydroxy-3-naphthoic
dimethylaminoethylbenzenesulfonamide.
(A) 41.25 grams of N-acetyl-oaanisidine were added
‘below 15° 0., with stirring, to 145 cc. of freshly distilled
chlorosul‘fonic acid. The temperature of the reaction mix
Do.
anilide.
30
The new raminobenzenesulfonamide compounds of the
invention are prepared by the following series of reac
_
OX
ture was then raised to 60° C. during 2 hours and then
allowed to cEall to room temperature. The reaction mix
ture was then poured into 500 grams of cracked ice with
vigorous stirring. Ice was added as necessary to keep‘ the
tions. The lo-alkoxyianiline compounds having the for
mulazl
(A)
‘
Example 9
25
35
temperature below 20° C. The product (34acetamin0-4
methoxybenzenesulfonylchloride)’ which precipitated was
recovered by ?ltration and washed thoroughly with ice
water.
(B) The slightly moist 3-acetamino-4emethoxybenzene
are acetylated to obtain com-pounds having the formula:
(B)
(')X
40
H
N-?GH;
lsulionyl chloride obtained ‘as ‘described in A Was ‘added
in small portions to 130 cc. of 'y-dimethylarninopropyl
amine with vigorous stirring. Considerable heat was
generated and after about 15 minutes a crystalline solid
began to separate. After about 4 hours \stinring when
the temperature \had dropped to about room tempera
O
ture -'a solution of 30 grams of sodium‘ carbonate in 125
The compounds having the Formula B are treated with
chlorosulronic acid to form the benzenesulfonyl chloride 45 cc. was added, with- stinring. The product which sep
arated was recovered :by ?ltration, Washed with water
compounds having the formula:
and ‘dried. 69 grams of 3=acetamino-4-methoxy-N-e/-di
(C)
ox
methylarninopropylbenzenesulfonamide were recovered as
% OOH a
T “g
1 ‘a white‘ solid.
50
(C) A mixture of the 69 grams of 3-acetamino-4
methoxy-N-y - dimethylaminopropylbenzenesulfonamide
obtained in B, 400 cc. of ‘absolute ethyl ‘alcohol ‘and 87.5
cc. of concentrated HCl was re?uxed for 2.5 hours. The
$0201
1 alcohol was distilled off, 100 cc. of water were addedand
The compounds having the formula C are reacted with 55 the mineral acid present was neutralized with- sodium
an amine having the formula:
carbonate. 3-arnino-4-methoxy-N-v - dimethylaminopro
(D)
H2NRN(R1)'z
to form compounds having the ‘formula:
(E)
OX
H
pyl'benzenesulfonamide was obtained as a gummy solid.
It was washed well with water by decantation and air
dried.
(D) It the diazo component is to be stored it is more
60
easily handled in its hydrochloride ‘salt form which is
prepared as follows. In C, after re?uxing for 2.5 hours,
—N-—€JOH;
O
25 0 cc. of alcohol-water lazeotrope were distilled off while
replacing it with 250 cc. of absolute ethyl alcohol. Dry
6a HCl was bubbled vigorously into the reaction mixture
.
I
R
SOzNRN(R1)2
I"
for 5 minutes and then 800 cc. of azeotrope was distilled‘
off replacing it with an equal volume of absolute ethyl
alcohol. The reaction mixture was then concentrated
E is removed by alkaline hydrolysis to obtain the new
under vacuum until a heavy precipitate formed. The
aminobenzenesulfonarnide compounds of the invention. 70 reaction mixture was cooled and the reaction product.
The acetyl group of the compounds having the Formula
X, R, R1 and N(R1)2 have the meaning previously as
the \dihydrochlo-ride’of the product of C, ‘was recovered
signed to them.
by ?ltration and dried ‘at 60° C.
B-Dimethylam-inoethylamine [H2NCH2CH2N ( CH3) 2] ,
p-diethylaminoethylamine, B-di-npropylaminoethylamine
[HzNcHzCHzN (n-C3H7) 2] ,
62 grams of a light
tan colored solid melting at 189° C. (dec.) which has
the correct elementary analysis for C, H, N, O and Cl
‘B - ‘di - n -— butylaminoethyl- 75 were obtained.
3,096,322
8
Example 10
50 grams of 3acetamino-4-methoxy-N~'y-dimethyl
sodium-alcohol or with hydrogen over Raney nickel to
give:
(G)
aminopropylbenzenesulfonarnide prepared as described in
Example 9B were added to a solution of 29.5 cc. of
concentrated hydrochloric acid and 15 cc. of concen
trated H2804 in 205 cc. ‘of water at 75° C. The reac
(2) Potassium phthalimide is condensed with a di-"
lbromoalkyl compound having the formula: Br(CH2)zBr
tion mixture resulting was then re?uxed for one hour,
cooled to 40° C. and ‘brought to a pH of 8.5 with dilute
aqueous sodium hydroxide. If this pH is exceeded it
to obtain C6H4(CO)2N(CH2)ZBr which is treated with‘
F to give
can \be adjusted by alternately adding acetic acid and
which is hydrolyzed with dilute mineral acid to give
sodium carbonate. The solution Was cooled and sodium
chloride was added until no more oil formed. The oily
(H)
layer was recovered, dissolved in acetone, ?ltered and the
acetone was removed by evaporation. 41 grams of 3
amino-4-methoxy-N - 3 - dimethylaminopropylbenzenesul
H2N(CH2)X+1N(R1)Z
the desired product.
H2N(CH2)ZN(R1)2
the desired product. Method 2 is the well—known Gabriel
15
synthesis.
In the two processes just described R1 represents an
alkyl radical having 1 to 4 carbon atoms, X is 1 or 2
Example 11
and Z is 2 or 3. Compounds having the Formula D
wherein N(R1)2 represents the morpholinyl radical or
138 grams of 3-acetarnino~4-methoxy-N-y-dimethylami
nopropylbenzenesulfonamide prepared as described in Ex 20 the piperidyl radical are obtained by using morpholine or
piperidine in place of an amine compound having the
ample 9B, 800 cc. of ethyl alcohol and 175 cc. of con
Formula F.
centrated hydrochloric acid were refluxed together for
The following example illustrates one way in which
2.5 hours. 500 cc. of liquid were distilled off while re
the azo compounds of the invention can be used to dye
placing it with 500 cc. of absolute ethyl alcohol. Dry
acrylonitrile polymer textile material. .1 gram of dye
HCl was bubbled vigorously into the reaction mixture
is dissolved by warming in 5 cc. of methyl Cellosolve.
for 5 minutes and then 1600 cc. of liquid were distilled
A 2% aqueous solution of a monionic surfactant, such as
o?’ while replacing it with an equal volume of absolute
Igepal CA (a polymerized ethylene oxide-alkylphenol
ethyl alcohol. The reaction mixture was then concen
condensation product), is added slowly until a ?ne
trated under vacuum to obtain the reaction product as
a heavy white precipitate. The reaction product, the 30 emulsion is obtained and then the dye mixture is brought
fonamide was thus obtained ‘as a viscous oil.
dihydrochloride of 3-amino~4-methoxy-N-y-dimethylarni
to a volume of 200 cc. with warm Water.
5 cc. of a
5% aqueous solution of formic acid or acetic acid are
added and then 10 vgrams of fabric made from an acrylic
and dried at 60° C. 123 grams of dried product were
?ber is entered and in the case of Orlon 42 the dyeing
obtained.
35 is carried out at the boil for one hour. In the case of
Example 12
nopropylbenzenesulfonamide, was recovered by ?ltration
66 grams of 3-acetamino-4-methoxybenzenesulfonyl
chloride were added with good stirring to 65 cc. of 5
diethylaminoethylamine. After stirring one hour longer
the reaction mixture was diluted by the addition of 15
grams of Na2CO3 dissolved in 65 cc. of water. An addi
tional 200 cc. of water were added and the oily pro
duct, 3-acetamino~4-methoxy-N-B-diethylaminoethylbcn
materials made of Verel acrylic ?ber the dyebath tem
perature should not exceed 90° C. in order to avoid
damage to the ?ber. The dyed material is then washed
well with water and dried.
The invention has been described in detail with par
rticular reference to preferred embodiments thereof, but
it will be understood that variations and modi?cations
can be effected within the spirit and scope of the in
zenesulfonamide, formed was recovered and washed
vention as described hereinabove and as de?ned in the
several times with water by decantaltion.
45 appended claims.
The oil obtained as just described was dissolved in a
We claim:
mixture of 250‘ cc. of ethyl alcohol and 55 cc. of con
1. The azo compounds having the formula:
centrated hydrochloric acid and the resulting mixture
was re?uxed for 5 hours.
About 1200 cc. of liquid were
distilled off while replacing it with an equal volume of 50
absolute ethyl alcohol.
The reaction mixture was then
OX
Hf.)
concentrated under vacuum and worked up as described
in Example 11. The product obtained was the dihydro—
chloride of 3-amino-4-methoxy-N-{3-diethylaminoethyl
benzenesulfonamide.
The new aminobenzenesulfonamide compounds of the
invention, such as those speci?cally mentioned herein
before, as well as 3~amino-4-ethoxy-N-B-diethylamino
I
H
SOzNRN (R1):
wherein X represents a member selected from the group
consisting of a methyl radical and an ethyl radical, R
following the procedures just described. It is not neces 60 represents an alkylene radical having 2 to 3 carbon
atoms, R1 represents an \alkyl radical having 1v to 4
sary to isolate the diazo component in its free amino
carbon atoms, N(R1)2 collectively represents a member
form or its hydrochloride form in order to use them in
selected from the group consisting of the morpholinyl
the preparation of the new azo dye compounds of the
radical and the piperidyl radical and R2 represents a
invention.
Many of the primary amines having the Formula D 65 monoeyclic iaryl nucleus of the benzene series devoid of
a water-solubilizing group.
.
are known compounds. Those that may not be speci
2. The azo compound having the formula:
?cally disclosed in the prior art can be prepared by the
methods used to prepare the known compounds.
ethylbenzensulfonamide, for example, can be prepared
Two general processes by which primary amines hav
ing the Formula D can be prepared are set forth here
infater:
( 1) An amine having the formula:
(F)
H2N(R1)2
is condensed with a chloroalkylnitrile having the formula:
Cl(CH2)XCN, and the product ogtained is reduced by 75
OOH;
6. The azo compound having the formula:
3. The azo compound having the formula:
0011,
H
0on3
HO GONGOCEB
|
We
01
H
SOaNCHzCHzCHgNKlHz):
4. The azo compound having the formula:
OCHa no (EON?
H
10
References Cited in the ?le of this patent
15
N:N8 Ha
O2NGHzCH2CHzN(CH3)z
5. The azo compound having the formula:
0 011a
HO
20
H
0 ON—
@Té?
SOQN OHaCH2GH2N (CH3) 2
(SCH,
UNITED STATES PATENTS
2,373,299
2,270,678
2,644,819
2,691,653
2,733,242
2,742,459
2,863,875
Dougherty __________ __ Apr. 10, 1945
Fischer ____________ __ Iran. 20,
1942
Dazzi ________________ __ July 7,
Williams ____________ .. Oct. 12,
Libby ______________ __ Jan. 31,
Fischer ____________ __ Apr. 17,
1953
1954
1956
1956
Bienent ________________ __ Dec. 9, 1958
FOREIGN PATENTS
25
761,085
1,222,318
France ______________ __ Jan. 3, 1934
France ______________ __ Jan. 18, 1960
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