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Патент USA US2130668

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2,130,668
I Patented Sept. 20, 1938
UNITED STATES PATENT OFFICE
2,130,088
‘
WETTING, CLEANSING, AND EMULSIFYING
AGENT
Fritz Giinther, Ludwigshafen-on-the-Rhine, Ger
many, assignor to I. G. Farbenlndustrie Ak
tiengesellschaft, Frankfort-on-the-Main, Ger
many, a corporation of Germany
No Drawing. Application December 9, 1927, Se
rial No. 239,003. In Germany December 11,
1926
'
.
23 Claims. "(01. zeoi-z'so')
'
ing
the
required
components
thereto. It is to be
The present invention relates to the manufac
ture and production of new wetting, cleansing understood that in the production of the new
products no heating or other strong condition
and emulsifying agents.
of working is applied, since otherwise condensa
I have found that products imparting to aque
5 ous liquids excellent wetting, cleansing and tion or other reactions would occur which may
emulsifying properties are obtained by mixing an leaicsl to the formation of water insoluble prod
organic acid wetting agent selected from the
When the substances are mixed no heat is ap
group consisting of sulfuric acid derivativesv of
high wetting power, that means true sulfonic plied and the usual reaction of an acid with a
l0 acids of high wetting power. or sulfuric acid base occurs, namely, the formation of a salt cor 10
esters of the nature of Turkey-red oil, and :Iesponding for example to the following equa
ons:
naphthenic acids, with up to equivalent amounts
uc
.
'
of nitrogen-containing organic bases. Organic’
sulfonic acids of high wetting power which are
15 to be employed according to the present inven
tion comprise only such acids of which a 0.5 per
cent aqueous solution of their sodium salt wets
a felt-like textile fabric, for example, of wool or
cotton in atthe most one hour, but preferably
20 in a much shorter time, for example in a few
minutes. Organic sulfonic acids of the said kind
which are particularly suitable for the purpose
of the present inventlon'are aromatic sulfonic
Mono-sulfuric
--
ester of com-
0
pound R
\N/
\
15
.H/ ——
R-S 0,-011 + if
> Suiionic acid
\ _'-» 12-8 0,
--
\
oi comrpoun'd
0
\(1— \>
H/
acids containing alkyl-, aralkyl-, cycloalkyl-, or
25 aryl groups, which may, if desired, be further
substituted, whether in the nucleus or in the side
chain, further sulfonic acids of aliphatic or hy
droaromatic compounds, for example the sulfo
n-co-on + i(
Oarboxyiic
25
\> ---> n-co
-_-
\
acid of com-
0
~ pound R
nation products of mineral oils, aliphatic tar
3o oils, naphthenic acids and the like, as well as the
known fat-splitting acids, or the ligno-sulfonic
acids contained in sul?te-cellulose waste liquor.
These acids yield excellent wetting, cleansing and
emulsifying agents when treated with organic
35 nitrogen-containing bases in the above speci?ed
amounts. As organic bases suitable for prepar
ing the said agents, according to the present in
vention, aliphatic amines, such as methylamine
or ethylamine, ‘mono-, di-, or triethanolamine,
40 but particularly the heterocyclic nitrogen-con
taining bases, such as pyridine and its homo
logues and derivatives, and the like, may be men
tioned.
The said components for manufacturing the
45 new products imparting to aqueous liquids a high
wetting, cleansing and emulsifying action may
be prepared before use by mixing them with
each other in the absence of water in up to
equivalent amounts, the nitrogenous base being
50 always employed in a substantial quantity, i. e.,
in a quantity of at least 10 per cent of the equiv
alent amount, or by preparing them in the form
of their salts by working in aqueous solution, or
they may be produced only in the liquid or prep
55 aration with which they are to be used, byadd
30
The fact that a salt is actually formed is evi
denced by the reduction of the acidity of the
solutions of the acids when the nitrogenous base
‘desired is added.
These salts, moreover, are
water-soluble salts since the formation of amides 35
or imides would become obvious by the insolu
bility of the products.
It is not essential for the purpose of this in—
vention that the equivalent quantity of the or
ganic nitrogen bases is added to the acids. Even 40
acids which are only partially so saturated ex
hibit an excellent wetting action.
Very useful
effects are also obtained with mixed salts pre
pared by adding to the said acids either several
different organic nitrogen bases, or by replacing 45
a portion of the latter by inorganic bases, such
as caustic soda, ammonia and the like.
For preparing aqueous liquids of high wetting
and cleansing properties it is generally su?lcient
to add to the liquids about 0.5 per cent of the 60
said preparations. Aqueous liquids of a'higher
concentration, however, may also be used. If
the said preparations are to be used for prepar
ing highly stable aqueous emulsions or suspen
sions, or even clear aqueous solutions of sub
2
stances insoluble in water, higher concentrations
of the preparations are often needed. Also dry
compomtions of solids, for instance dyestu?s,
with the agents according to the present inven
tion may be prepared, which when diluted with
of aliphatic amines and monocyclic pyridine
b.
2. As new articles of manufacture wetting,
cleansing and emulsifying products comprising
a naphthalene sulfonic acid substituted by an
water furnish stable suspensions or even clear. alkyl group, and a substantial proportion up‘ to
solutions of the said solids.
The following examples further illustrate the
nature of this invention, which however is not
10 restricted to these examples. The parts are by
weight.
cleansing and emulsifying products comprising
a naphthalene sulfonic acid substituted by an
9.1%! group, and a substantial proportion up to
Example 1
If an acid sulphuric‘ ester of oleic acid, pre
15 pared by treating oleic acid with sulfuric acid,
be treated with an equivalent amount of caustic
soda solution on the one hand and an equivalent
amount of pyridine on the other, the aqueous so
lution, which contains the mixed pyridine and so
20 dium salt of the acid sulfuric ester of_oleic acid,
displays a far greater capacity for wettingtextiles
than an equally concentrated aqueous solution of
the acid sulfuric ester of oleic acid either neutral
ized with caustic soda solution or in the free
25
equivalent amounts of a monocyclic pyridine
base.
3. As new articles of manufacture wetting,
state.
'
Ezrample 2
equivalent amounts ofpyridine,
4. As new articles of manufacture the salts
formed by an organic acid wetting agent selected
from the group consisting of organic sulfonic
acids and sulfuric esters of high wetting power
with an organic ‘nitrogen containing base selected
from the group consisting of aliphatic amines
and monocyclic pyridine bases.
20
5. As new articles of manufacture the salts
formed by a naphthalene sulfonic acid substituted
by an alkyl group, with an organic nitrogen
containing base selected from the group consist
tug of aliphatic amines and monocyclic pyridine
ases.
To a solution of one part of dibutylnaphtha=
‘so
lene-sulfonic acid in 200 parts of water, 0.3 part
of pyridine is added and the solution is made up
to 250 parts with water. The wetting properties
of the resulting solution containing the corre
sponding pyridine salt are considerably better
than those of a solution of the free acid or its
sodium salt of the same concentration.
35
_
The corresponding salts of isobutylamine,
triethanolamine, or other amines, behave in an
equally favorable manner. The dibutylnaphtha
lane-sulfonic acid may be replaced by other sul
fonic acids of the character de?ned. such as those
40 of methyl-, ethyl-, propyl- or also cycloalkyl
substituted organic compounds.
Example 3
An approximately 0.5 per cent solution of a
45 crude gas-oil sulfonic acid, i. e., the sulfonation
product of a brown coal tar fraction boiling be
tween 225° and 360° 0., in water is treated with
the calculated amount of dimethylaniline. The
resulting solution containing the salt of the
50 said acid with dimethylaniline possesses excellent
wetting properties.
‘
6. As new articles of manufacture the salts
formed by a naphthalene sulfonic acid substituted
ggisan alkyl group, with a monocyclic pyridine
e.
7. As new articles of manufacture the salts
formed by a naphthalene sulfonic acid substituted
by an alhl group with pyridine.
30
.
8. A process of producing wetting, cleansing
and emulsifying agents which comprises mixing 35
a wetting agent selected from the group consist
ing of organic sulfonic acids and sulfuric esters
of high wetting power with about equivalent
amounts of an organic nitrogen containing base
selected from the group consisting of aliphatic
amines and monocyclic heterocyclic bases, in 40
which nitrogen is the hetero atom.
9. Wetting, cleansing and emulsifying products
comprising an organic acid wetting agent selected
from the group consisting of organic sulfonic
acids and sulfuric esters of high wetting power 45
and about equivalent amounts of an organic
nitrogen containing base selected from the group
consisting of aliphatic amines and monocyclic
h'eterocyclic bases in which nitrogen is the hetero
a cm.
50
10. As new articles of manufacture wetting,
Ezmmple 4
cleansing and emulsifying products comprising
To 5 parts of a tri-isopropylbenzenesulfonic
55 acid the equivalent quantity of isobutylamine
is added, and the mixture is dissolved in su?icient
a naphthalene sulfonic acid substituted by an
alkyl group and about equivalent amounts of an
' water to form 1000 parts. The solution contain
the group consisting of aliphatic amines and
ing the corresponding salts has very good wet
ting properties.
60
Example 5
2 parts of naphthenic acid are treated with
equivalent quantities of either methylamine,
isobutylamine, or triethanolamine, and dissolved
65 in sumcient water to form 500 parts.
25
All these
solutions containing the corresponding salts
exhibit very good wetting properties, substantially
more than the corresponding sodium salt.
What I claim is:
1. As_ new articles of manufacture wetting,
70
cleansing and emulsifying products comprising
a naphthalene sulfonic acid substituted by an
alkyl group, and a substantial proportion up to
equivaleint amounts of an organic nitrogen-con
75. taining base selected from the group consisting
organic nitrogen—containing base selected from
monocyclic pyridine bases.
55
,
11. As a new articles of manufacture wetting,
cleansing and emulsifying products comprising a
naphthalene sulfonic acid substituted by an allnrl 60
group and about equivalent amounts of a mono
cyclic pyridine base.
12. As new articles of manufacture wetting,
cleansing and emulsifying products comprising a 65
naphthalene sulfonic acid substituted by an alkyl
group and about equivalent amounts of pyridine.
13. As new articles of manufacture the salts
of alkyl naphthalene sulphonic acids with alkylol
amines.
14. As a new articles of manufacture a salt
70
of a dibutyl naphthalene suiphonic acid with
triethanol amine.
15. The process of producing a substance
which will form a soluble compound with salts 75
3
of the alkaline earth of hard waters, consisting
naphthalene aliphatically substituted in the
in adding ethanolamines to sulphonated oils.
16. A sulphonated oleaginous compound ?uidi
nucleus.
ucts essentially comprising an admixture of a
?ed by an ethanolamine.
monocyclic heterocyclic base in which nitrogen
17. A suiphonated oleaginous compound ?uidi
?ed by tri-ethanoiamine.
'
'
21. Wetting, cleansing and emulsifying prod
'
18. Wetting, cleansing and emulsifying prod
ucts essentially comprising an admixture of a
monocyclic heterocyclic base in which nitrogen
is the hetero atom, and an aromatic sulio 'acid,
said acid being an acid of high wetting power.
19. Wetting; cleansing and emulsifying prod
7. ‘ucts essentially comprising an admixture of a
monocyclic heterocyclic base in which nitrogen
is the hetero atom and a sulio acid of the
"naphthalene group.
20. Wetting. cleansing and emulsifying prod
' ucts essentially comprising an admixture of a
monocyclic heterocyclic base in which nitrogen
s0 is the hetero .atom and a sulfo acid of an aromatic >
is’ the hetero atom and an alkylated sulfo acid
of the naphthalene group.
_
22. Wetting, cleansing and emulsifying prod
ucts essentially comprising an admixture of a
water-soluble monocyclic heterocyclic base in 10
which nitrogen is the hetero atom and aromatic
sulfo acid, said acid being an acid of high wet
ting power.
23. Wetting, cleansing and emulsifying prod
ucts essentially comprising an admixture of a 15
sulfo acid of an aromatic poly-nuclear hydro
carbon and a monocyclic heterocyclic base in
which nitrogen is the hetero atom, said acid being
an acid of high wetting power.
FRITZ GUN‘I'I-IER.
20
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