Improved Manufacture of Green and Bluish Green Coloring Matters.
Year: 1889

page_text: Date of Application, 1st Apr., 1889
Complete Specification Left. 24th Dec.. 1359-Accepted, 25th Jan., 1990
PROVISIONAL SPECIFICATION.
[Communicated from abroad by the FARBWERKE VORMALS LUCIUS MEISTER AND
BRUNING, of Hoechst-am-Main, in the Empire of Germany, a Company carrying
on business as Chemical Manufacturers.]
Improved Manufacture of Green and Bluish Green Coloring Matters.
I, OLIVER IMRAY of No. 28 Southampton Buildings, Chincery Lane, in the County
of Middlesex. Fellow of the Institute of Patent Agents, do hereby declare the nature
of this invention to be as follows:-
In my application for Letters Patent No. 127968 dated 4th September were
described acid coloring matters being derivatives of the metaoxydiamidotriphenyl-
methan; my correspondents have since discovered another series of bodies, which also
are derivatives of the metaoxydiamidotriphenylmethan and their sulphonic acids and
which form coloring matters remarkable for very valuable qualities.
The processes for producing these new bodies are identical with those described in
my application for Letters Patent No. 127968, mutatis mutandis, so that it will
scarcely be necessary to give here again a minute description of these processes.
In the application for Letters Patent mentioned above was described, sub, I A, a.
process for the production of metaoxytetralkyldiamidotriphenylmethans consisting in
the conversion of the meta amidotetralkyl-diamidotriphenylmethans into the corre-
sponding oxyleuco bases by means of nitrous acid. In like manner, as explained there,
my correspondents have produced the following bases:
meta-oxytrimethylbenzyl-diamidotriphenyl-methan

page_text: eta-oxyethylmethyldibenzyl-diamidotriphenylmethan non symmetric
C, H, OH
✓CH,
CH
CH, N C₂ H5
N.
CH, N/CH-C₁₂ H¸
CH-CH
The same bases are obtained also by working according to the process described
my said application for Letters Patent 12796 of 1888 sub. I B for the conden-
tion of tertiary aromatic bases with meta-oxybenzaldehyde, namely; by causing to
act in the presence of de-hydrating agents:
1 part by molecular weight of meta-oxybenzaldehyde respectively upon :
.
1 part molecular weight of dimethylaniline and 1 part molecular weight of
inethylbenzylaniline,
1 part molecular weight of diethylaniline and 1 part molecular weight of
ethylbenzylaniline,
1 part molecular weight of dimethylaniline and 1 part molecular weight of
ethylbenzylaniline,
1 part molecular weight of diethylaniline and 1 part molecular weight of
methylbenzylaniline,
1 part molecular weight of methylbenzylaniline and 1 part molecular weight of
ethylbenzylaniline,
1 part molecular weight of ethylmethylaniline and 1 part molecular weight of
methylbenzlaniline,
1 part molecular weight of methylethylaniline and 1 part molecular weight of
ethylbenzylaniline,
1 part molecular weight of dimethylaniline and 1 part molecular weight of
dibenzylaniline,
1 part molecular weight of diethylaniline and 1 part molecular weight of
dibenzylaniline,
1 part molecular weight of ethylmethylaniline and 1 part molecular weight of
dibenzylaniline.

page_text: By these condensations are formed unsymetrically substituted leuco bases, as was
explained in the application for Letters Patent No. 127965 with regard to meta-
nitro, meta-amido, and meta-oxy-dimethyl diethyl diami lotriphenylmethans
The new bases are with regard to their physical and chemical properties, similar in
every respects to the meta oxytetralkylliamidotriphenylmethans described in the
application for Letters Patent No. 1279689.
The conversion of the leuco bases enumerated above into the lenco sulphonic acids
is carried out in manner described in the application for Letters Patent No. 127965
sub. III example 2 and the oxidation of the leuco sulphonic acids as set forth in that
application sub. IV.
The new coloring matters are in form of copper red powders of metallic lustre,
dissolving easily in water with blue tint, and their solutions behave in regard to mineral
acids, carbonic and caustic alkalies, in manner described in the application for Letters
Patent No. 1279688.
The new coloring matters dye silk and wool in acid bath quite even blue green
shades, remarkable for great resistance to the action of soap an I light.
Dated this 1st day of Amil 1300
ABEL & IMRAY,
Agents for the Applicant.
COMPLETE SPECIFICATION.
Improved Manufacture of Green and Bluish-green Coloring
Matters.
1, OLIVER IMRAY of No. 28 Southampton Buildings, Chancery Lane, in the County
of Middlesex, Fellow of the Institute of Patent Agents, do hereby declare the nature
of this invention and in what manner the same is to be performed, to be particularly
described and ascertained in and by the following statement:-
In the specification to Letters Patent No. 12796 of 1888 were described acid
coloring matters being derivatives of the metaoxy-diamidotriphenylmethan; my
correspondents have since discovered another series of bodies which also are
derivatives of the metaoxy-diamidotriphenylmethan and their sulphonic acids which
form coloring matters remarkable for very valuable qualities.
The processes for producing these new bodies are identical with those described in
ny application for Letters Patent No. 12796 of 1888, mutatis mutandis, so that
it will scarcely be necessary to give here again a minute description of these
processes.
In the specification to the said Letters Patent was described, sub I A, a process
for the production of metaoxytetralkyldiamido-triphenylmethans consisting in the
conversion of the meta amidotetralkyl-diamido-triphenylmethans into the corre-
sponding oxy leuco bases by means of nitrous acid.
In like manner, as explained there, my correspondents, in substituting for the
meta-amidotetralkyldiamidotriphenylmethans, the corresponding meta-amido leuco

page_text: The same bases are obtained also by working according to the process described in
said application for Letters Patent 12796 of 1888 sub. I B for the condensation
tertiary aromatic bases with meta oxybenzaldehyde, namely; by causing to react
the presence of de-hydrating agents:
1 part by molecular weight of meta-oxybenzaldehyde respectively upon :
1 part molecular weight of diamethylaniline and 1 part molecular weight of
methylbenzylaniline;
1 part molecular weight of diethylaniline and 1 part molecular weight of
ethylbenzylaniline;
1 part molecular weight of dimethylaniline and 1 part molecular weight of
ethylbenzylaniline;
1 part molecular weight of diethylaniline and 1 part molecular weight of
methylbenzylaniline;
1 part molecular weight of methylbenzylaniline and 1 part molecular weight of
ethylbenzylaniline ;
1 part molecular weight of ethylmethylaniline and 1 part molecular weight of
methylbenzylaniline;
1 part molecular weight of methylethylaniline and 1 part molecular weight of
ethylbenzylaniline;
1 part molecular weight of dimethylaniline and 1 part molecular weight of
dibenzylaniline;
1 part molecular weight of diethylaniline and 1 part molecular weight of
dibenzylaniline ;
1 part molecular weight of ethylmethylaniline and 1 part molecular weight
of dibenzylaniline.
By those condensations are formed unsymetrically substituted leuco bases, as was
lained in the specification to Letters Patent No. 12796 of 1888 with regard to meia-
ro, meta-amido, and meta-oxy-dimethyl-diethyl diamidotriphenylmethans
CHR (m)

page_text: mineral acids, carbonic and caustic alkalies, in manner described in the specification
to Letters Patent No. 12796 of 1888.
The new coloring matters dye silk and wool in acid bath quite even blue green
shades remarkable for great resistance to the action of soap and light.
Having now particularly described and ascertained the nature of this inven-
tion and in what manner the same is to be performed,, I declare that what I
claim is :-
1. The manufacture of meta-oxytetralkyl-liamidotriphenylmethan, namely
A the production of:
meta-oxytrimethylbenzyldiamido triphenylmethan,
meta-oxytriethylbenzyldiamido triphenylmethan,
meta-oxydimethylethylbenzyl diamido triphenylmethan,
meta-oxydiethylmethylbenzyldiamido triphenylmethan,
meta-oxyethylmethyldibenzyldiamido triphenylmethan, symmetric,
meta-oxymethylethylmethylbenzyl-diamido triphenylmethan,
meta-oxymethylethylethylbenzyldiomidotriphenylmethan,
meta-oxydimethyldibenzyldiamido iriphenylmethan
non-symmetric,
meta-oxydiethyldibenzyldiamidotriphenylmethan non-symmetric,
meta-oxyethylmethyldi benzyldiamido-triphenylmethan non symmetric.
By the substitution in the process described in the specification to patent 12796 of
1888, for the bases enumerated sub. I A, the meta-anido leuco bases corresponding
to the meta-oxyleuco bases of the malachite green series hereinbefore mentioned.
B. The production of the meta-oxytetralkyldiamido triphenylmethans hereinbefore
enumerated by causing to act, in manner described in the specification to patent
No. 12796 of 1888-under I B, metaoxybenzal-dehyde in the presence of dehydrating
agents, such as sulphuric acid and chloride of zinc, respectively upon:
-
1 part by molecular weight of dimethylaniline and 1 part by molecular weight
of methylbenzylaniline;
1 part by molecular weight of diethylaniline and 1 part by molecular weight
of ethylbenzylaniline ;
1 part by molecular weight of dimethylaniline and 1 part by molecular weight
of ethylbenzylaniline ;
1 part by molecular weight of diethylaniline and 1 part by molecular weight
of methylbenzylaniline;
1 part by molecular weight of methylbenzylaniline and 1 part by molecular
weight of ethylbenzylaniline;
1 part by molecular weight of ethylmethylaniline and 1 part by molecular
weight of methylbenzylaniline;
1 part by molecular weight of methylethylaniline and 1 part by molecular
weight of ethylbenzylaniline;
1 part by molecular weight of dimethylaniline and 1 part by molecular weight
of dibenzylaniline ;
1 part by molecular weight of diethylaniline and 1 part by molecular weight
of dibenzylaniline ;
1 part by imolecular weight of ethylmethylaniline and 1 part by molecular
weight of dibenzylaniline.
2. The production of the sulphonic acids of the leuco bases enumerated in the
first claim by treating these leuco bases according to the process described in the
specification to patent No. 12796 of 1888 under III..
3. The production of fast acid coloring matters, by oxidating the sulphonic acids
of the lenco bases enunièrated in the first claim in the manner described in the
specification to patent 12796 of 1888 under IV.
Dated this 24th day of December 1889.
ABEL & IMKAY,
Agents for the Applicant.