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Патент USA US2120401

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Patented June 14, 1938
>
UNITED STATES
_
‘2,120,401’
PATENT OFFICE
2,120,401
Y SULPHO -ACETONITRILE DYESTUFFS
Friedrich Felix and Wilhelm Huber, Basel, Swit
zerland, assignors to the ?rm of Society of
Chemical Industry in Basle, Basel, Switzer
land
No Drawing. Application April 3, 1936, Serial
No. 72,644. In Switzerland April 5, 1935
7 Claims. (Cl. 260-—99.30)
The present invention relates to new products nitrile and thiophenesulpho-acetonitrile. The
of the general formula
aryl and aralkyl sulpho-acetonitriles may contain
further substitutents in the aromatic nucleus such
as hydroxy-groups, amino-groups or-substituted
5
EEQN/\Ra
amino-groups.
'
As compounds of the general formula‘
wherein R1 represents the radical of an organic
sulphone, R2 and R3 represent alkyl radicals of
10 which at least one radical contains an O—R
group in which R stands for a member of the
group consisting of hydrogen, alkyl, and organic
acyl radicals, which products do not form salts
stable in water with alkalies.
15
The products have therefore the formula
Ra
10
wherein R2 and R3 have the meaning indicated
above, there may be named:
(N-alkyl-N-hydroxyalkyl) -aminobenzaldehydes
such as (N-methyl-N-hydroxyethyl) -para-amino
benzaldehyde,
(N-ethyl-N -hydroxyethy1) - para -
aminobenzaldehyde, (N-ethyl-N-hydroxypropyl) -
para-aminobenzaldehyde, (N-propyl-N-hydroxy
ethyl)-para-aminobenzaldehyde, (N-dihydroxy
\
20
R3
wherein R1 represents alkyl, aralkyl, cycloalkyl
and aryl, and R2 and R3 have the meaning indi
cated above. These products are obtained by
treating compounds of the general formula
alkyl) -para-aminobenzaldehyde, such as (N-di
hydroxyethyl)-para-aminobenzaldehyde, (N-di
hydroxypropyl) -para-aminobenzaldehyde, (N-al
kyl - N - alkoxyalkyl) - para -- aminobenzaldehydes
such as (N-methyl-N-methoxyethyl) para-amino
benzaldehyde,
(N-ethyl-N-methoxyethyl) - para
aminobenzaldehyde,
para-aminobenzaldehyde,
and aryl, with molecular quantities of aromatic
aldehydes of the general formula
ethyl) —para-aminobenzaldehy_de, (N-dialkoxyal
30
R2
MHON/
\
kyl) -para-aminobenzaldehy-des such as (N-di
methoxyethyl)~para-aminobenzaldehyde, (N-al
Ra
organic acyl.
benzaldehyde,
(N-ethyl - N - acetoxyethyl) - para -
aminobenzaldehyde,
(N - ethyl - N- propionyl) para-aminobenzaldehyde, (N .- diacetoxy - ethyl) para-aminobenzaldehyde,
(N - hydroxyalkyl - N -
35
alkoxyalkyl) -para-amino-benzaldehyde, (N- hy
As compounds of the general formula
droxyethyl-N-methoxyethyl) - para-aminobenzal
dehyde,
N- bis -dihydroxypropyl) - para — amino -
benzaldehyde, (N-hydroxyethyl-N-hy-droxychlo
wherein R1 has the signi?cation indicated above, ropropyl) -para-aminobenzaldehyde, (N-methoxy
there may particularly be mentioned:
Alkylsulpho-acetonitriles, such as methylsul
ethyl-N- hydroxychloropropyl) - para-aminobenz
aldehyde, (N - methoxyethyl - N- a-methoxy-B-hy
pho-acetonitrile, ethylsulpho-acetonitri1e, propyl
droxy-propyl)-para-aminobenzaldehyde, (N-hy
45 sulpho-acetonitrile, butylsulpho-acetonitrile, al
lylsulpho-acetonitrile, benzylsulpho-acetonitrile;
arylsulpho-acetonitriles such as phenylsulpho
droxyethyl) -N- a - methoxy - 5 -hydroxy - propyl) -
para-aminobenzaldehyde and the like.
in water and are of yellow to orange color; they
such as chlorobenZenesulpho-acetonitrile, bromo
dissolve in organic solvents, for instance acetone >
iodobenzenesulpho -
alkoxybenzenesulpho - acetonitriles
such as methoxybenzenesulpho-acetonitrile; tol
uenesulpho-acetonitriles; xylenesulpho-acetoni
triles; _ nitrobenzenesulpho-acetonitriles; naph
thylsulpho-acetonitriles; cyclohexylsulpho-aceto-'
40
4-5
The new condensation products are insoluble
acetonitrile; halogen-benzenesulpho-acetonitriles
50 benzenesulpho - acetonitrile,
55
30
such as (N-methyl-N-acetoxyethyl) -para-amino
group consisting of hydrogen, alkyl and an
acetonitrile;
25
(N-propyl - N - ethoxy -
kyl-N-acyloxyethyl) - para - amino- benzaldehydes
wherein R2 and R3 contain at least one O-R
35 group in which R stands for a member of the
40
(N- ethyl - N - ethoxyethyl) -
wherein R1 represents alkyl, aralkyl, cycloalkyl
or ethyl acetate, to intensively green—yellow to 50
yellow solutions. On this account they ?nd ap
plication as transparent dyestuffs for lacquers or
the like which are made from a basis of natural
and arti?cial resins, nitro cellulose, acetyl cellu
lose, or the like.
They may also be‘ used for 55
2-.
2,120,401
-.
dyeing arti?cial materials for instance conden
sation products from phenols or urea and form
aldehyde. They are particularly suitable for
dyeing cellulose esters and ethers, more particu
larly acetate arti?cial silk, and they produce on
What we claim 1s:— I
1. The sulpho-acetonitrile dyestu?s of the gen
eral formula
these materials dyeings which are characterized
by their clarity and excellent properties of
fastness.
‘
The following examples illustrate the inven
10
tion, the parts being by weight:
Example 1
18.1 parts of phenylsulpho-acetonitrile and 20.7
parts of (N-ethyl-N-methoxyethyl) -para-amlno
benzaldehyde are dissolved together in 250 cc. of
alcohol and after addition of a few drops of a
strong base, for instance piperidine or some alkali
or a sodium alcoholate, the solution is boiled for
some time under re?ux. After a short time the
solution becomes intensely yellow owing to the
formation of the ‘condensation. product and boil
ing is continued until the intensity of the color
no longer increases, this indicating the end of
the reaction. The mass is allowed to cool while
stirring, during which the condensation product
of the formula
CH
35
separates. It is a yellow powder soluble in or
ganic solvents like acetone or ethyl acetate to
40
green-yellow solutions and dyeing after suitable
suspension, for example when ground with dis
persing agents such as sulphite cellulose liquor
or sulphonated residues from the benzaldehyde
manufacture and water, acetate arti?cial silk
45
fast green-yellow tints.
Example 2
18.1 parts of phenysulpho-acetonitrile are dis
solved together with 19.3 parts of (N-ethyl-N
hydroxyethyl) -para-amino-benzaldehyde in alco
hol and after addition of a few drops of piperi
dine the solution is boiled for some time under
re?ux. When the reaction is complete the whole
is cooled, while stirring, whereupon the conden
sation product of the formula
CH
60
wherein R1 represents a radical of the group con
sisting of aryl, alkyl, aralkyl and cycloalkyl, R2 10
and R3 represent members of the group consist
ing of substituted and unsubstituted alkyl radi
cals of which at least one is substituted by an
OR group in which R stands for a member of
the group consisting of hydrogen, alkyl and an
organic acyl radical, which products do not form
salts stable in water with alkalies, and are yellow
to orange colored powders dissolving in ethyl ace
tate to similar solutions and dyeing cellulose
20
esters and ethers similar tints.
2. The sulpho-acetonitrile dyestuffs of the gen
eral formula
R2
25
wherein R1 represents an aryl radical of the
benzene series, R2 and R3 represent members of
the group consisting of substituted and unsub
stituted alkyl radicals of which at least one is
substituted by an OR group of which R stands
for a member of the group consisting of hydro
gen, alkyl and an organic acyl radical, which
products do not form salts stable in water with
alkalies, and are yellow to orange colored powders
dissolving in ethyl acetate to similar solutions and
dyeing cellulose esters and ethers similar tints.
3. The sulpho-acetonitrile dyestuffs of the gen
40
eral formula
Rr-SOr-C-CEN
R2
\
Rs
wherein R1 represents an aryl radical of the ben
zene series, R2 and R3 represent members of the
group consisting of substituted and unsubsti
tuted alkyl radicals of which one at least is a
-CHz-CH2—O-—R group in which R stands for '
a member of the group consisting of hydrogen,
alkyl and an organic acyl radical, which products
do not form salts stable in water with alkalies,
and are yellow to orange colored powders, dis
55
solving in ethyl acetate to similar solutions and
dyeing cellulose esters and ethers similar tints.
4. The sulpho-acetonitrile dyestuffs of the gen
eral formula.
CHz-CHrR:
CHz-CHrRs
65
crystallizes. It is a yellow powder and soluble in
organic solvents like acetone or ethyl acetate to a
green-yellow solution and dyeing, under suitable
suspension, acetate arti?cial silk fast green-yel
wherein R1 represents an aryl radical of the 65
benzene series, R2 represents a member of the
group consisting of H, OH, O-alkyl and O-acyl,
is used, for example methylsulpho-acetonitrile or
acyl meaning the radical of an organic acid, and
R3 represents a member of the group consisting
of OH, O-alkyl and O-acyl, acyl meaning the 70
radical of an organic ‘acid, which products do
not form salts stable in water with alkalies, and
are yellow to orange colored powders dissolving
ethylsulpho-acetonitrile or another alkylsulpho
acetonitrile.
cellulose esters and ethers similar tints; '
low tints.
Similar condensation products are obtained
when instead of phenylsulpho-acetonitrile there
in ethyl acetate to similar solutions and dyeing
76
2,120,401
5. The sulpho-acetonitrile dyestuff of the gen
eral formula
R1—s0,—("J—0EN
CI
3
wherein R1 represents a radical of the benzene
series selected from the group of the benzene and
toluene radicals, which product is a yellow pow
der dissolving in ethyl acetate to green-yellow so
lutions and dyeing cellulose esters and ethers
similar tints.
7. The sulpho-acetonitrile dyestuff of the gen
eral formula
10
10
wherein R1 represents a radical of the benzene
series selected from the group of the benzene and
toluene radicals, which product is a yellow pow
der dissolving in ethyl acetate to green-yellow
solutions and dyeing cellulose esters and ethers
similar tints.
6. The sulpho-acetonltrile dyestu? of the gen
eral formula
20
15
wherein R1 represents a radical of the benzene
series selected from the group of the benzene
and toluene radicals, which product is a yellow 20
powder dissolving in‘ethyl acetate to green-yellow
solutions and dyeing cellulose esters and ethers
similar tints.
25
FRIEDRICH FELIX.
WILHELM HUBER.
25
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