The Preparation of New Compounds of Hexamethylenetetramine.
Year: 1899

page_text: Date of Application, 4th Mar.. 1899
Complete Specification Left, 30th Nov., 1899-Accepted, 27th Jan., 1900
PROVISIONAL SPECIFICATION.
The Preparation of New Compounds of Hexamethylenetetramine.
I, LUDWIG STANGE, of Goethestrasse, Offenbach-on-the-Main, in the German
Empire, Chemist, do hereby declare the nature of this invention to be as follows:-
This invention has for its object to manufacture from hexamethylenetetramine,
antiseptic, antibacterial and relatively stable bodies (as such or in the form of their
halogen derivatives) which form new compounds of the said hexamethylenetetra-
mine.
The invention is based upon the recent discovery that hexamethylenetetramine
is suitable for the production of such new substances which remain comparatively
stable during their favourable action and that for this purpose it is caused to act
(either as such or in the form of its compounds, for example halogenalkyl derivatives
of hexamethylenetetramine) upon tetraiodopyrrol (as such or in the form of its
halogen derivates) or upon sulphonic acids (which may be in a halogenised condition)
of the aromatic series-for instance of phenol, aniline, as hereinafter inore particularly
described. The new compounds containing pyrrol are, in contradistinction to the
iodoform compounds, namely iodoformal and iodoformin as manufactured by the.
Firm Dr L. C. Marquart of Beuel-Bonn, remarkably stable when boiled in water and
they also remain unchanged in the air. When digested with acids and alkalies they
split up into their components from which they form molecular products of
addition.
By the action of tetraiodopyrrol upon hexamethylenetetramine and ethyliodide
there is formed tetraiodopyrrol-hexamethylenetetramine-ethyliodide. The product
crystallises in small yellow crystals the solubility of which is almost the same as
that of the above mentioned body.
If, instead of iodopyrrol, bromopyrrol bromide or chloropyrrol be used the
corresponding products are obtained.
The tetraiodopyrrol hexamethylenetetramine (which was employed for experimental
work in the Bacteriological Institute in Berlin by Dr. Aufrecht) exhibits very strong
antiseptic and antibacterial properties; it surpasses in this respect iodoform, iodol,
aristol and is also somewhat soluble in water, quite odourless and not so easily
decomposed as these two substances.

page_text: EXAMPLE 6.
If instead of sulphanilic acid (Example 4) naphtolsulphonic acid (Nevile Winter's
Acid) be used, by proceeding in a similar manner a deliquescent somewhat yellow
product of naphtolsulphonicacidhexamethylenetetramine is obtained.
Dated this 31st day of Jannary 1899
G. F. REDFERN & Co.,
4, South Street, Finsbury, London, Agents for the Applicant.
G. F. REDFERN & Co.,
4, South Street, Finsbury, London, Agents for the Applicant.
The Freparation of New Compounds of Hexamethylenetetramine.
I, LUDWIG STANGE, of Goethestrasse, Offenbach-on-the-Main, in the German
Empire, Chemist, 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 :-
This invention has for its object to manufacture from hexamethylenetetramine,
antiseptic, antibacterial and relatively stable bodies (as such or in the form of their
halogen derivatives) which form new compounds of the said hexamethylenetetramine.
The invention is based upon the recent discovery that hexamethylenetetramine is
suitable for the production of such new substances which remain comparatively
stable during their favourable action and that for this purpose it is caused to act
(either as such or in the form of its compounds, for example halogenalkyl derivatives
of hexamethylenetetramine) upon tetraiodopyrrol (as such or in the form of its
halogen derivatives) or upon sulphonic acids (which may be in a halogenised
condition) of the aromatic series--for instance of phenol, aniline, as hereinafter
more particularly described. The new compounds containing pyrrol are, in contra-
distinction to the iodoform compounds, namely, iodoformal and iodoformin as
manufactured by the Firm Dr. L. C. Marquart of Beuel-Bonn, remarkably stable

page_text: 1. The preparation of new antiseptically and antibacterially acting bodies by means
of hexamethylenetetramine, by bringing it (either as such or in the form of its
compounds) into contact with halogen pyrrols and aromatic sulphonic acids (either
as such or in the form of their halogen derivatives) and allowing chemical reaction
to take place, substantially as hereinbefore described.
2. Bodies which act only antiseptically and antibacterially manufactured from
hexamethylenetetramine, substantially as herein before described.
Dated the 30th day of November 1899.
G. F. REDFERN & Co.,
4, South Street, Finsbury, London, Agents for the Applicant.