The Manufacture or Production of Colouring Matters and Materials therefor.
Year: 1893

page_text: Date of Application, 6th Sept., 1893
Complete Specification Left, 6th June, 1894-Accepted, 7th July, 1894
Communicated from abroad by THE FARBENFABRIKEN vormals FRIEDRICH
BAYER & Co., of Elberfeld, in the Empire of Germany.]
The Manufacture or Production of Colouring Matters and Materials
therefor.
I HENRY EDWARD NEWTON of The Office for Patents, 6 Bream's Buildings,
Chancery Lane in the County of London, Patent Agent, do hereby declare the
nature of this invention to be as follows:-
My foreign correspondents have described in the Specification of application for
Letters Patent No. 8898, dated 3rd May 1893, the production of dialkylnaph-
thylene diamines, or sulpho acids thereof, which process can be effected by heating
alpha or beta naphthylamine sulpho acids (especially those which contain an amido-
group and a sulpho group in the position meta one to another) with a primary
amine and a salt of the primary amine, with or without the addition of benzoic
acid or the like substances capable of facilitating the reaction.
In the said processes, not only an alkylation of the amido group takes place,
but at the same time a sulpho group (preferably that in the position meta to the
amido group) is separated, and replaced by the so-called alkylamido group under
the conditions mentioned in the said Specification. If, for instance, a₁-naphthyl-
amine--mono sulpho acid is heated with aniline and aniline hydro chloride,
symmetrical diphenyl-a₁ ẞ-meta naphthylene diamine is formed, sulphurous acid
being disengaged during this operation. The naphthylamine poly sulpho acids
containing a sulpho group in the position ineta to the amido group, yield, in a
similar manner, the respective diphenylnaphthylene diamine sulpho acids. The
process also proceeds in the same manner, if aniline is replaced by its homologues
or analogues, viz., on heating the homologues or analogues of aniline with alpha- or
beta naphthylamine sulpho acids and a salt of the amine employed.
My foreign correspondents have now found, that naphthylene diamine sulpho
acids (especially those which contain at least one sulpho group in the position meta
to an amido-group) are capable of re-acting in the manner herein before defined,
both amido groups being substituted in this case. For instance, a, a, naphthylene
diamine ẞ, mono sulpho acid (described in the German Patent No. 67,017) yields
in such a way triphenyl a₁ ẞ, a triamido naphthalene, whilst a₁ a naphthylene
diamine B, B, disulpho acid, and a, a, naphthylene diamine 3, 3, disulpho acid, are
converted into the respective tetra phenyl tetra amido naphthalenes. Hence it
follows, that the chemical action which takes place once on the production of
diphenyl a B naphthylene diamine, occurs twice when employing the said
naphthylene diamine disulpho acids.
The process is effected in a manner analogous to that described in the aforesaid
Specification No. 8898 of 1893. In order to illustrate this process, the following
example is given, the parts being by weight.

page_text: of steam), and the residue is mixed with muriatic acid. The insoluble tetra
tolyl tetra amido naphthalene is isolated by filtration. It is almost insoluble in
water, but readily dissolves in alcohol. On adding concentrated muriatic acid to its
alcoholic solution, a hydrochloride of the tetra tolyl tetra amido naphthalene is
formed, which has the property of becoming decomposed, when brought into contact
with water.
Products similar to that obtainable as described in the preceding example, result,
if either para toluidine is replaced by aniline, ortho toluidine, meta xylidine, alpha
naphthylamine, beta naphthylamine, or the like, or if a₁ a naphthylene diamine
B, mono sulpho acid, a, a, naphthylene diamine B, B disulpho acid, or the like, are
employed in place of the a₁ a naphthylene diamine B, B disulpho acid.
My foreign correspondents have also ascertained that in the processes described
in the aforesaid Specification No. 8898 of 1893, alpha or beta naphthol sulpho acids
can be used in place of the respective alpha or beta naphthylamine sulpho acids
employed therein, dialkylnaphthylene diamines, or dialkylnaphthylene diamine
sulpho acids, likewise being formed.
The following naphthol sulpho acids, for instance, can be used, viz.,
a-naphthol-ẞ, mono sulpho acid (described in the German Patent No. 57910),
a naphthol Bẞ, disulpho acid (obtainable as described in the German Patent
No. 38281 from naphthalene a, ẞ, B, trisulpho acid, by melting with alkalies),
a naphthol ẞ, ẞ, disulpho acid (obtainable as described in the German Patent
No. 38281 from naphthalene a₁ B, B, trisulpho acid, by melting with alkalies)
a, naphthol a disulpho acid (described in the German Patent No. 45776),
a naphthol Bẞs a trisulpho acid (described in the German Patent No. 56058),
Bnaphthol a, a, disulpho acid C of the German Patent No. 65997, or the like.
The B, naphthol a, ẞ, disulpho acid, hitherto unknown, can likewise be employed.
It is prepared for the purpose by my foreign correspondents, by diazotising the
corresponding B₁ naphthylamine a, ẞ, disulpho acid, and boiling the resulting diazo
compound with water.
The conversion of naphthol sulpho acids in dialkylnaphthylene diamines, or
dialkylnaphthylene diamine sulpho acids, is illustrated by the following example;
the parts are by weight.
SECOND EXAMPLE.
PRODUCTION OF DIPHENYL NAPHTHYLENE DIAMINE FROM a₁ NAPHTHOL
ẞ, MONO-SULPHO ACID.
1 part of a naphthol B, sulphonate of sodium is mixed with 4 parts of aniline
and 1 part of aniline hydrochloride. The resulting mixture is heated for about
4. hours at from 150 to 170 degrees centigrade, being agitated the while. The mass
is then. poured into diluted muriatic acid, and the formed diphenyl naphthylene
diamine which is separated, is filtered off from the solution containing the aniline
hydrochloride. The diphenyl naphthylene diamine can be purified by dissolving
an alcohol, and adding muriatic acid to the alcoholic solution, the hydrochloride of
the diamine being thus precipitated.
Other dialkylnaphthylene diamines, or dialkylnaphthylene diamine sulpho acids,
result, if, in this second example, either the a, naphthol B, sulpho acid employed
is replaced by other naphthol sulpho acids, or if, in place of aniline, other amido
products (such as toluidine, xylidine, alpha or beta naphthylamine, or the like) are
used. The alkylated naphthylene diamines thus obtainable are identical with those
which result on employing the corresponding naphthylamine sulpho acids in place
of naphthol sulpho acids.
The researches of my foreign correspondents have also shown, that in place of
the naphthylene diamine sulpho acids (as above described), the corresponding
amido naphthol sulpho acids, or dihydroxy naphthalene sulpho acids, can likewise
be used for producing so called polyalkyl polyamido naphthalenes, or sulpho acids
thereof. For instance, a, amido a, naphthol ẞ, sulpho acid (obtainable by melting
uaphthylamine epsilon disulpho acid with alkalies), or a1 amido a naphthol
a

page_text: sulpho acid (obtainable by melting a naphthylamine ẞ, a disulpho acid with
alkalies), or as a dihydroxynaphthalene B, sulpho acid (obtainable by melting
a naphthol epsilon disulpho acid with alkalies), yield, when employed in the said
process, products identical with that which results on employing a, a, naphthylene
diamine B, sulpho acid. The products, which are formed from a₁ α, amido
naphthol B B disulpho acid (described in the German Patent No. 69722) or
aja, dihydroxynaphthalene ẞ, ẞ, disulpho acid (described in the German Patent
No. 67563), by heating them with primary aromatic amines and salts thereof, are
identical with the substituted tetra amido naphthalenes obtainable from a₁ a naph-
thylene diamine ẞ, ẞ, disulpho acid. The 6, 6, dihydroxynaphthalene a sulpho
acid, can likewise be used in place of the corresponding B₁ B3 naphthylene
diamine a, sulpho acid.
My foreign correspondents have further found, that the substituted naphthylene
diamines, polyalkyl polyamido naphthylenes, and derivatives thereof herein before
defined, and containing at least two alkylamido groups in the position meta one to
another, are capable of reacting with the nitroso compounds of secondary or tertiary
aromatic amines, or with substances acting in a manner similar to that shown by
nitroso compounds, valuable dye stuffs being thus produced. This condensation
process is effected preferably in the presence of suitable solvents or diluents (such
as glacial acetic acid, alcohol, naphthalene, aniline, or naphthylamine, phenol,
naphthol, or similar substances), and at a higher temperature. If aniline or phenol,
or analogous amines or phenols of the benzene series, or of the naphthalene series,
are used, products result which in general are distinguishable by the greenish or
green shades produced.
The process of producing these colouring-matters is analogous to that which
my foreign correspondents have described in the Specification of the aforesaid
application No. 8898 of 1893.
It is merely necessary to employ the substituted naphthylene diamines, or
polyalkyl polyamido naphthalenes, or derivatives thereof, in place of the dialkyl-
naphthylene diamines, or their sulpho derivatives used in the said application.
Amongst these colouring-matters, those which are obtainable from nitroso
derivatives and dialkyl naphthylene diamines, or trialkyltriamido naphthalenes, or
tetra alkyl tetra amido naphthalenes, and which contain no sulpho groups, are
preferably treated with sulphonating agents, sulpho acids being thus obtained
which are especially suitable for dyeing wool in acid baths. Analogous sulpho
acids are directly obtained, if either nitroso compounds of secondary or tertiary
amines are condensed with sulpho acids of alkylated amido naphthalenes, or if
nitroso compounds of secondary or tertiary aromatic amido sulpho acids are
condensed with alkylated amido naphthalenes, or sulpho derivatives thereof.
The sulpho acids of alkylated amido naphthalenes (such as those derived from
dialkylnaphthylene diamine, trialkyltriamido naphthalene, tetra alkyl tetra amido
naphthalene, or the like) are obtained either by sulphonating the alkylated
amido naphthalene compounds (viz., dialkyl naphthylene diamine, trialkyl triamido
naphthalene, tetra alkyl tetra amido naphthalene, or the like), or in accordance
with the process herein before defined, that is to say, by heating naphthylamine
polysulpho acids, naphthol polysulpho acids, naphthylene diamine polysulpho acids,
amidonaphthol polysulpho acids, or dihydroxynaphthalene polysulpho acids, with a
primary aromatic amine and a salt thereof.
The researches of my foreign correspondents have also shown, that in place of
nitroso compounds, all those products can be used which react in the same or a
similar manner, for instance, quinone dichloroimide and analogues thereof, or azo
compounds obtainable from diazo derivatives and primary or secondary or tertiary
amines, or substituted amines (particularly amido sulpho acids), the same or
analogous colouring-matters being thus obtained. The process for producing these
dye-stuffs is analogous to that which my foreign correspondents have described in the
Specification of my application for Letters Patent No. 11892, dated 16th June 1893,
and which consists in condensing such products as react in a manner analogous or

page_text: similar to that of nitroso compounds (for instance, quinone dichloroimide or
analogues thereof, or azo products obtainable from diazo derivatives and primary
or secondary or tertiary amines), with substituted naphthylene diamines, or sulpho
derivatives thereof. My foreign correspondents have also ascertained, that in
place of chloroimides and nitroso compounds, the corresponding reduction products
(such as paraphenylene diamine, para-toluylene diamine, para amido dialkyl aniline,
or analogous diamines, or sulpho or other derivatives thereof) can be used; in the
latter case, the said diamines are mixed with dialkylnaphthylene diamines, trialkyl
triamido naphthalenes, tetra alkyl tetra amido naphthalenes or the like, or sulpho
or other derivatives thereof, and the resulting mixtures are oxidised in a suitable
manner, for instance, by means of ferric chloride, potassium bichromate, manganese
dioxide, or the like.
Those of the resulting colouring-matters which are destitute of sulpho groups,
or contain but one sulpho group, are preferably treated with sulphonating agents, in
order to obtain dye-stuffs which are either easily soluble, or at least dissolve with
greater readiness than the original products.
Dated this 6th day of September 1892
NEWTON & SON,
Agents for the Applicant.
COMPLETE SPECIFICATION.
The Manufacture or Production of Colouring Matters and Materials
therefor.
I HENRY EDWARD NEWTON of The Office for Patents, 6 Bream's Buildings,
Chancery Lane in the County of London, Patent Agent, 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 :-
"
My foreign correspondents have described in the Specification of application
for Letters Patent No. 8898, dated 3rd May 1893, the production of dialkyl alpha
beta, naphthylene-diamines and dialkyl alpha, beta, naphthylene diamine sulphonic
acids, which process consists in heating uaphthylamine sulphonic acids, or alkaline
salts of naphthylamine sulphonic acids containing a sulphonic group in the "meta
position relatively to the amido group, with primary aromatic amines and a salt of
the amine used, adding benzoic acid or other agents capable of facilitating the
action, if desirable. In the said processes, not only does un alkylation of the amido
group take place, but the sulphonic group in the meta position relatively to the
amido group, is at the same time separated, and displaced by the so-called alkyl
amido group. If, for instance, alpha, naphthylaminebeta, monosulphonic acid is
heated with aniline and aniline hydrochloride symmetrical diphenyl alpha, beta,
naphthylene diamine is formed, sulphurous acid being disengaged during this
operation. The naphthylamine polysulphonic acids also containing a sulphonic
group in the "meta position relatively to the amido group, yield, in a similar
manner, the corresponding diphenyl alpha, beta, naphthylene diamine sulphonic
acids. The process also proceeds in the same manner, if, instead of aniline, its
homologues or analogues are used.
"
My foreign correspondents have now found that, in the processes described in the
aforesaid Specification No. 8898 of 1893, alpha or betanaphtholsulphonic acids
containing a sulphonic group in the "meta" position relatively to the hydroxylic
group, can be used in place of naphthylamine sulphonic acids employed therein,
dialkylalpha, beta, naphthylenediamines, or dialkylalpha, beta, naphthylenediamine
sulphonic acids, being formed.
The following naphtholsulphonic acids, for instance, can be used, viz., alpha,
naphthol beta, monosulphonic acid (described in the German Patent No. 57,910),
alpha, naphthol beta, betas disulphonic acid (obtainable, as described in the
German Patent No. 38281, from naphthalene alpha, beta, beta, trisulphonic acid

page_text: by melting with alkalies), alpha, naphthol beta, beta, disulphonic acid (obtainable,
as described in the German Patent No. 38281, from naphthalene alpha, beta, beta,
trisulphonic acid by melting with alkalies), alpha, naphthol beta, alpha, disulphonic
acid (described in the German Patent No. 45776), alpha, naphthol beta, beta,
alpha, trisulphonic acid (described in the German Patent No. 56058), beta, naphthol
alpha, alpha, disulphonic acid C (described in the German Patent No. 65997),
or the like. The hitherto unknown beta, naphtholalpha, beta, disulphonic acid can
also be used; it is prepared for the purpose by my foreign correspondents by
diazotising the corresponding beta, naphthylamine alpha, beta, disulphonic acid and
boiling the diazo compound with water.
The conversion of naphtholsuiphonic acids into dialkyl alpha, beta, naphthylene
diamines, or dialkyl alpha, beta, naphthylene diaminesulphonic acids, is illustrated
by the following example; the parts are by weight.
PRODUCTION OF
DIPHENYL ALPHA BETA, NAPHTHYLENE DIAMINE
ALPHA NAPHTHOL BETA2 MONOSULPHONIC ACID.
FROM
1 part of alpha, naphthol beta, sulphonate of sodium is mixed with 4 parts of
aniline and 1 part of aniline hydrochloride. The resulting mixture is heated
during about 4 hours at from 150 to 170 degrees centigrade, being agitated the
while. The mass is then poured into diluted muriatic acid, and the diphenyl-
naphthylenediamine which separates is filtered off from the solution containing the
aniline hydrochloride. The diphenylnaphthylenediamine can be purified by
dissolving it in alcohol, and adding muriatic acid to the solution, the hydrochloride
of the diamine being thus precipitated. It is identical with the diphenyl alpha,
beta, naphthylene diamine obtainable by the process described in the Specification
of application for Letters Patent No. 8898 of 1893, by heating alpha,
naphthylamine-beta,-monosulphonic acid with aniline and a salt of aniline.
Other dialkyl alpha, beta, naphthylene diamines, or dialkyl alpha beta,
naphthylenediaminesulphonic acids, are formed, if, in the foregoing example,
instead of the alpha, naphthol beta, sulphonic acid therein used, either the corre-
sponding quantities of others of the naphtholsulphonic acids hereinbefore defined,
or, in place of aniline, other primary amido products (such as orthotoluidine,
paratoluidine, or the like) are used. The dialkylnaphthylene diamines, or
dialkylnaphthylene diamine sulphonic acids, thus obtainable, are identical with
those which are formed when the corresponding naphthylamine sulphonic acids
are used in place of naphtholsulphonic acids, that is to say, on using corresponding
quantities of alpha, naphthol beta, beta, disulpbonic acid, alpha, naphthol beta, beta
disulphonic acid, alpha, naphthol beta, alpha, disulphonic acid, or alpha, naphthol
beta, beta, alpha-trisulphonic acid, in the process illustrated by the foregoing example,
the following diphenylnaphthylene diamine sulphonic acids are obtained, miz.,
diphenyl alpha, beta, naphthylene diamine beta, monosulphonic acid, diphenylalpha,
beta, naphthylene diamine beta monosulphonic acid, diphenyl alpha, beta,
naphthylene diamine alpha, monosulphonic acid, and diphenyl alpha, beta, naphthylene
diamine beta, alpha, disulphonic acid.
If, instead of aniline and a salt of aniline, the equivalent quantities of ortho-
toluidine or paratoluidine, and a salt of ortho- or para-toluidine are used, the corre-
sponding diorthotolyl or di-para tolyl alpha, beta, naphthylene diamines, and
diorthotolyl or dipara-tolyl alpha, beta, naphthylene diamine sulphonic acids, are
produced.
These dialkyl alpha, beta, naphthylene diamines, and sulphonic acids thereof,
are already described in the Specification of the said application No. 8898 of 1893.
On using beta, naphthol alpha-alpha, disulphonic acid in the process illustrated
by the above example, diphenyl beta, alpha, naphthylene diamine alpha, mono-
sulphonic acid is obtained, which can also be termed diphenyl alpha, beta,
naphthylene diamine alpha, monosulphonic acid, whilst the above mentioned isomeric

page_text: beta, naphthol alpha, beta, disulphonic acid is thus converted into diphenyl beta,
alpha, naphthylene diamine beta-monosulphonic, or diphenyl-alpha beta
naphthylene diamine beta, monosulphonic acid. The corresponding diorthotolyl
and diparatolyl derivatives, viz., diorthotolyl alpha beta,-naphthylenediamine
alpha, monosulphonic acid, and diparatolyl alpha, beta, naphthylene diamine
alpha, monosulphonic acid, diorthotolyl alpha, beta, naphthylene diamine beta,
monosulphonic acid, and diparatolyl-alpha, beta, naphthylenediamine-beta, mono-
sulphonic acid, are obtained in an analogous manner by means of orthotoluidine
and paratoluidine, and a salt of the toluidine used. Of the last-named sulphonic
acids, viz., diphenyl, diorthotolyl, and diparatolyl alpha, beta, naphthylene diamine
alpha monosulphonic acid, diphenyl, diorthotolyl and diparatolyl alpha, beta,
naphthylamine diamine beta, monosulphonic acid; the last three acids have also
been obtained by my foreign correspondents (as described in the said Specification
No. 8898 of 1893) by heating alpha, naphthylamine beta, beta, disulphonic acid
with aniline, orthotoluidine, or paratoluidine, respectively, and a salt of the amine
used, whilst the first three acids, viz., the diphenyl alpha, beta, naphthylene
diamine alpha, monosulphonic acid, diorthotolyl alpha, beta, naphthylene diamine
alpha, monosulphonic acid, and di-paratolyl alpha, beta, naphthylene diamine
alpha, monosulphonic acid, could not be produced by means of the last named
process, as the corresponding alpha, naphthylamine beta, alpha, disulphonic acid
was hitherto unknown.
The conversion of the naphthol sulphonic acids into dialkyl alpha, beta,
naphthylene diamines, or dialkyl alpha, beta, naphthylene diamine sulphonic acids,
can be facilitated by adding benzoic acid (or other agents capable of facilitating
the action) to the mixture before heating.
The diphenyl alpha, beta, naphthylene diamine alpha, monosulphonic acid,
diorthotolyl alpha, beta, naphthylene diamine alpha, monosulphonic acid, and
diparatolyl alpha, beta, naphthylene diamine alpha, monosulphonic acid, in general
show the same chemical behaviour as the other dialkyl alpha, beta, naphthylene
diamine monsulphonic acids described in the Specification of the said application
No. 8898 of 1893. Of course the aforesaid diphenyl alpha, beta, naphthylene
diamine alpha, monosulphonic acid, diorthotolyl alpha, beta, naphthylenediamine
alpha, monosulphonic acid, diparatolyl alpha, beta, naphthylene diamine alpha,
monosulphonic acid, diphenyl alpha, beta, naphthylene diamine beta, mono-
sulphonic acid, diorthotolyl alpha, beta, naphthylenediamine beta, monosulphonic
acid, and diparatolyl alpha, beta, naphthylenediamine beta; monosulphonic acid,
can also be produced by heating, respectively, beta, naphthylamine alpha, alpha
disulphonic acid, or beta, naphthylamine alpha; beta disulphonic acid, with
aniline, orthotoluidine, or paratoluidine, and a salt of the amine used, that is to
say, in a manner analogous to that described in the Specification of the aforesaid
application No. 8898 of 1893.
My foreign correspondents have further found that the dialkylalpha, beta,
naphthylene diamines and dialkyl alpha beta, naphthylene diamine sulphonic
acids, produced as hereinbefore defined from naphthol sulphonic acids, when
treated with the nitroso derivatives of secondary or tertiary aromatic amines or
.amido sulphonic acids, or with substances acting in a manner similar to that shown
by nitroso compounds, yield dye-stuffs which are, in part, identical with those
obtainable as described in the Specifications of applications for Letters Patent
No. 8898, dated 3rd May 1893, and No. 11892, dated 16th June 1893. The
coloring matters which may be formed from the diphenyl, diorthotolyl, and dipara-
tolyl alpha betas naphthylene diamine alpha, monosulphonic acid hereinbefore
defined, however, are not yet described in the last mentioned two Specifications.
The condensation of the said diphenyl alpha, beta, naphthylene diamine alpha,
monosulphonic acid, diorthotolyl alpha, beta, naphthylene diamine alpha, mono-
sulphonic acid, and diparatolyl alpha, beta, naphthylene diamine alpha, mono-
:sulphonic acid, with nitroso derivatives or other compounds acting in the same or
a similar manner, is effected preferably in the presence of suitable solvents or

page_text: diluents (such as glacial acetic acid, alcohol, naphthalene, aniline, or naphthylamine,.
phenol, naphthol, or similar substances), and at an elevated temperature. If
aniline or phenol, or analogous amines or phenols of the benzene series or of
the naphthalene series, are used, products are formed which in general are
distinguishable by being more bluish-green or greener in shade.
The process of producing these coloring matters with the aid of nitroso-
compounds is analogous to that which my foreign correspondents have described.
in the Specification of the aforesaid application No. 8898 of 1893. It is merely
necessary to use the diphenyl, diorthotolyl, or diparatolyl alpha beta, naphthylene
diamine alpha, monosulphonic acid in place of the dialkyl alpha beta, naphthylene--
diamines, or dialkyl alpha, beta, naphthylene diaminesulphonic acids used in the
process described in the last-named Specification.
If, in place of nitroso compounds, those products are used which act in the same-
or a similar manner, for instance, quinone dichlorimide, and analogues thereof, or
azo compounds formed by the combination of diazo compounds with primary,
secondary, or tertiary amines, or amido sulphonic acids of the benzene or naph--
thalene series, or amidophenols or amidophenolethers, the process can be effected
in a manner analogous to that which my foreign correspondents have described in
the Specification of application for Letters Patent No. 11892, dated 16th June 1893.
My foreign correspondents have also ascertained that, in place of chlorimides
and nitroso compounds, the corresponding reduction products, viz., alkylated para-
diamines, or paradiamine sulphonic acids containing, in one of the amido groups,
either a single or two alkyl radicles, can be used; in the latter case the alkylated
paradiamines or paradiaminesulphonic acids are subjected, together with the afore-
said diphenyl, diorthotolyl, or diparatolyl alpha, beta, naphthylene diamine alpha¸.
monosulphonic acid, to a joint oxidation in the presence of suitable solvents or
diluents, for instance, by means of ferric chloride, potassium bichromate, manganese
dioxide, or the like. This oxidation is effected in the same manner as described in
the Specification of the said application No. 11892 of 1893.
Those of the coloring matters derived from diphenyl, diorthotolyl, or diparatolyl
alpha, beta, naphthylene diamine alpha, monosulphonic acid which contain but one
sulphonic group, may with advantage be treated with sulphonating agents, in order
to obtain more soluble dye stuffs.
The dye stuffs obtained as hereinbefore defined from diphenyl alpha, beta,
naphthylene diamine alpha, monosulphonic acid, diorthotolyl alpha, beta, naph-
thylene diamine alpha, monosulphonic acid, or diparatolyl alpha, beta, naphthylene.
diamine alpha, monosulphonic acid, in general possess chemical and dyeing
properties similar to those possessed by the analogous dye-stuffs derived from.
dialkyl alpha, beta, naphthylenediamine alpha, monosulphonic acid.
Having now particularly described and ascertained the nature of the said inven-
tion and in what manner the same is to be performed, as communicated to me.
from abroad, I declare that what I claim is :-
1. The production of dialkyl alpha,-beta, naphthylene diamines, or dialkyl
alpha, beta, naphthylene diamine sulphonic acids, in which an aromatic alkyl group.
is substituted for a hydrogen atom of each of the two amido groups, which process.
consists in heating naphtholsulphonic acids, or alkaline salts of naphthol-sulphonic
acids, containing a sulphonic group in the " meta position relatively to the
hydroxyl group, with primary aromatic amines, and a salt of the amine used, at
elevated temperatures, adding benzoic acid or other agents capable of facilitating
the action, if desirable.
גי
2. The process for producing diphenyl-alpha, beta, naphthylene diamine, diorthoto-
lyl-alpha, beta, naphthylene diamine, or diparatolyl-alpha beta, naphthylene
diamine, which process consists in heating alpha, naphthol beta, monosulphonic
acid, or alkaline salts thereof, with either aniline or orthotoluidine, or paratoluidine,
and a salt of the amine used, at elevated temperatures, together with benzoic acid
or other agents capable of facilitating the action, if desirable.

page_text: 3. The process for producing diphenyl alphar beta, naphthylene diamine beta,
monosulphonic acid, diphenyl alpha, beta, naphthylene diamine beta monosulphonic
acid, diphenyl alpha, beta, naphthylene diamine alpha, monosulphonic acid,
diphenyl alpha, beta, naphthylene diamine beta, alpha, disulphonic acid, or the
corresponding diorthotolyl and diparatolyl alpha, beta, naphthylene diamine
sulphonic acids, by heating either alpha, naphthol beta, betas disulphonic acid,
alpha naphthol beta, beta disulphonic acid, alpha, naphthol betas alpha
disulphonic acid, or alpha, naphthol beta, beta, alpha, trisulphonic acid, or an
alkaline salt thereof, at an elevated temperature, with either aniline or ortho
toluidine or para toluidine, and a salt of the amine used, together with benzoic acid
or other agents capable of facilitating the action, if desirable.
4. The production of diphenyl-beta, alpha, naphthylene diamine alpha mono-
sulphonic acid (or diphenyl alpha, beta, naphthylene diamine-alpha, monosulphonic
acid), diphenyl beta, alpha, naphthylene diamine beta, monosulphonic acid (or
diphenyl alpha beta, naphthylene diamine beta, monosulphonic acid) or the
corresponding diorthotolyl and diparatolyl alpha, beta, naphthylene diamine
sulphonic acids, by heating either beta, naphthol alpha, alpha, disulphonic acid, or
beta, naphthol alpha, beta, disulphonic acid, or an alkaline salt thereof, at an
elevated temperature, with either aniline or ortho toluidine or paratoluidine, and
a salt of the amine used, together with benzoic acid or other agents capable of
facilitating the action, if desirable.
5. The use of the dialkyl alpha, beta, naphthylene diamines, or dialkyl alpha,
beta, naphthylene diamine sulphonic acids, obtained as defined in the foregoing
claims, for producing basic azine dye-stuffs, or sulphonic acids thereof, by means of
the processes described in the Specifications No. 8898 of 1893 and No. 11892
of 1893.
6. The production of dye-stuffs by condensing nitroso derivatives of secondary
or tertiary aromatic amines or amido sulphonic acids (such as nitroso monomethyl-
aniline, nitroso dimethylaniline, nitrosodiethylaniline, nitroso diphenylamine,
nitrosoethylbenzylaniline sulphonic acid) with diphenyl, diorthotoly!, or dipara-
tolyl alpha, beta, naphthylene diamine alphas monosulphonic acid.
7. The process for producing dye stuffs by allowing diphenyl, diorthotolyl or
diparatolyl alpha beta, naphthylene diamine alpha, monosulphonic acid, to act in
the presence of acid, neutral, or basic solvents or diluents, at more or less
elevated temperatures, on quinone dichlorimide, or azo products formed by the
combination of diazo compounds with primary, secondary, or tertiary amines, or
amidosulphonic acids of the benzene or naphthalene series, or with amido phenols
or amidophenolethers.
8. The production of coloring matters by subjecting diphenyl, diorthotolyl, or
diparatolyl alpha, beta, naphthylene diamine alphas monosulphonic acid, together
with alkylated para diamines, or para diamine sulphonic acids, containing in one of
their amido groups either a single or two alkyl radicles, to a joint oxidation in the
presence of suitable solvents or diluents.
9. The conversion of the dye-stuffs obtainable as described in the foregoing
sixth, seventh, and eighth claims, into more readily soluble coloring matters by a
subsequent treatment with sulphonating agents.
10. As new products of manufacture :-
a) diphenyl, diorthotolyl, and diparatolyl alpha, beta, naphthylene diamine
alpha, monosulphonic acid;
b) the new coloring matters produced by the processes described in the
foregoing Claims 6, 7, 8, and 9, or by any other means affording the same
result.
Dated this 6th day of June 1894.
NEWTON & SON,
Agents for the Applicant.
NEWTON & SON,
Agents for the Applicant.