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Патент USA US2404913

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Patented July 30,1946
2,404,913 '
Lee Leiserson, Rochester, N. Y., assignor to Vir
ginia Smelting Company, West Norfolk, Va., a.
corporation of Maine
Application April 28,1943, Serial No. 484,923
8 Claims.
(01. 252-353)
where a. ?ber is acted upon.
As some of the
My invention relates to agents for reducing
the surface tension of liquids and more especially
to the use of these compounds as lifting and
dispersing agents to assist other surface active
agents, such as wetting agents, detergents and
other substances which promote wetting, pene
tration, swelling, frothing, and dispersing of ma
terials by a solvent.
An object of my invention is the production of
the result obtained is better and of more even
superior materials for effecting such changes by 10
lifting agent remains on the ?ber after removal
from the solution, it promotes rewetting on im
mersion in water and promotes ease of handling
in subsequent textile operations. In dyeing, the
lifting agent has a great importance. It facili
tates the dispersion of clumps and aggregates of
color particles. It insures better solubility and
Ketones can effect lowering of surface tension
but when they are combined with efficient wetting
agents and operate as lifting agents the mixture
of such combinations is more than additive and
not only is more specific and effective than would
substantially increase the wetting, penetrating,
swelling, frothing and dispersing action of the 15 be expected, but the lifting agent has a solvent
action, as above explained, which makes it an
solution, and otherwise improve the action of
excellent leveling agent for dye baths, and as
the materials with which they are associated.
above set forth, assists by remaining to some ex
The action of a wetting agent or any surface
tent with the ?ber in the future handling of the
active compound is primarily due to adsorption.
If a textile is immersed in a solution with wetting 20 materials.
The lifting agents greatly increase the effec
properties, the adsorbed air ?lm on the surface
tiveness of wetting agents, and other surface ac
is ?rstdisplaced, due to the selective adsorption
tive compounds in many ?elds of use, such as the
of wetting agent molecules. Wetting agents, and
combining these assistants with other surface ac
tive materials. It has been found that the effect
petroleum industry, metal processing, the paint
lifting agents, both reduce the surface tension
of aqueous solutions.‘ They do this because they 25 industry, cleaners and cleaning compounds, the
rubber industry, agriculture and cosmetics, tex
have a limited solubility in water. The molecules
tiles both natural and synthetic, to give but a
of the surface active compound are literally
few ?elds of use.
squeezed out from the interior of the liquid to
The single sheet of drawings-is a table showing
the surface. The effectiveness of a particular
compound in reducing the surface tension de 30 the increased e?iclency of one wetting agent when ~
mixed with the lifting agents.
pends on the orientation of the molecules at the
A principal feature of the present invention
interface, liquid-air, and the disrupting e?ect
resides in the discovery that ketones having 5 to
this orientation has on the forces between the
12 carbon atoms can be used effectively as as
water molecules at the interface. The best ma
terials effectively reduce the surface tension of 35 sistants in conjunction with other materialswith
surface active properties, such as sodium alkyl
water to that of a hydrocarbon. The reduction
sulfates, sodium oleate, sodium alkyl naphthalene
of surface tension means that the liquid spreads
sulfonates, etc. To show the importance of these
easily and quickly over a large surface. Thus,
ketones as assistants or lifting agents when used
when a ?ber is immersed in a wetting agent solu- '
with other materials having surface active prop
tion, the air, ‘then oil or wax, is displaced from
erties, below is given a procedure for a canvas
the ?ber due to the selective adsorption of the
disc wetting test, which procedure has been em
wetting agent molecules. The solution spreads
ployed with a number of. combinations of various
quickly over the large surface of the fiber and
ketones operating as lifting agents in admixture
the wetting agent acts as a bond between two
substances that might not otherwise adhere to 45 with certain agents for reducing the surface ten
sion of liquids. The data given hereinafter show
each other.
the remarkable results obtained by the use of
The action of a lifting agent, which is gen
these lifting agents in combination with these
erally used in low concentrations where it would
surface active materials.
have little or no effect if used alone, is to intro
Canvas disc wetting tests are employed to com
duce into the wetting agent solution another sub
pare the wetting ability of various wetting ma
stance that will be preferentially adsorbed. It
terials. The following test was reported by Sey
thus prolongs the time a solution may be used
ferth and Morgan in the American Dyestufl.’ Re
before exhaustion of the wetting agent. The
porter, 2'7, 525 (1938) and in Chemical Abstracts
lifting agent has a solvent action for oils and
waxes and facilitates their removal ‘from the ?ber, 55 32, 8789 (1938).
‘ Example 4
The tests consists of measuring the sinking
time of a 1" diameter, number 6 canvas disc in
Methyl n-‘amyl ketone as a lift
a known solution. Conditions of temperature,
concentration of wetting agent, water hardness
and pH are controlled. The canvas used in these
ing agent __________________ ..
cc. per liter- 0.8
Sodium ditertiary butyl naph
thalene sultonate as a wetting
tests was natural color and "unwaterprooted.”
All tests were made with discs cut from the same
___________________ __
strip of cloth, to eliminate variations due to the
g. per liter__ 0.3
Example 5
Isophorone as a lifting agent--. ' cc. per 1it_er_ 03
The solutions, for the tests were made from -a 10_ Sodium ditertiary butyl naph
thalene sulionate'as a wetting
stock 1% solution. All were made‘with distilled
agent ____________________ .._. g. per Men. 0.3
water. The proper ampunt oi‘. concentrated so
lution was measured into a ‘500 cc. volumetric _' ’
?ask. An organic solvent, ii any. was measured
I Eaample 6
out and -,added. The mixture‘was then diluted
is Methyl n-butyl ketone/as’a litt-
with distilled water to 500 cc. This amount, of
the solution tobe tested was placed-in a 600 cc.
I Sdium ditertiary butyl naph
ing agent _________________ _- cc. per liter- 0.8
thalene suli'onate as a wetting
A Gooch funnel 1%" in diameter and ‘
agent ____‘ ________________ __ g. per men. 0.3
having a barrel 3" long is inverted in the so
lution and the whole'is ‘brought to the desired 20
temperature, usually 25' degrees C. Working
rapidly the Gooch funnel is removed, a canvas
Example 7
agent.T ________ _7 ________ __
disc placed in the tunnel which then is again
Sodium. ditertiary butyl naph
inserted into the solution; at the same time a
stop watch is started. The time-recordedis that 26 ’ thalene sulfonate as a wetting
agent ____ __ ______________ .._
interval required for the disc .to sink to touch
cc. per liter- 0.8
g. per Men. 0.3
the bottom of the beaker. After stirring- the so- '
I Other examples of combinations which I have
lution the test may be repeated for cheeke'on the
found to possess excellent properties are as fol- .
sinking time. To get consistent results it is'nec
essary to insert the disc so that when it‘ wets. 30
one bubble of, air comes oil at a time-from the
same position near the edge of the disc ' The
data may beplotted on logarithmic paper;
points, when connected, give a straight line.
_' Epample 8
‘ '
naphthalene sulfonate- 4parts z..- 1 g. per liter
Seyferth and Morgan-report the deviation from 35 Methyl n-amyl ketone__ Sports
mean wetting time to be 9.4% .
The tests which are reported hereinafter were
Methyl ‘n-amyl ketone-- 5
The table in Figure 1 shows the results of the
solutions containing ketoneg as lilting agents, to-_
gether with a wetting agent. All solutions con
tained 0.3 gram per liter of sodium ditertiary
Alcohol, .(methyL‘ ethylv
Eaample 3 '
or less
5 as a lifting agent ________ _. cc. per liter- 0.8
250° C. at 20 mm. and cam
- Ekrample 14
40% sodium ditertiary butyl
naphthalene sulfonate from
a fraction boiling at 190_
Sodium ditertiary butyl naph
250'’ C. at 20 mm. in methyl
thalene sulfonate as a wetting
___________________ __ 8. W1‘ liter"
Sodium ditertiary butyl naph~
phor in the ratio of 10:1...__ g. per Men. 0.66
1,1,3 - trimethylcyclohexanone
Example 13
agent _..-.._-_g.'._-_;.-_- ______ __ g. per liter‘... 0.3
Methyl pr0py1ket0ne____ 4 parts
Sodium ditertiary butyl naph
or less
naphthalene sulfonate- 6 parts __ l g. per liter
Example 12
agent (cloudy sat. solution) _, cc. per liter- 0.8 65
thalene sulfonate as a wetting
naphthalene sulfonate- 4yparts }__ 1 g. per liter
Isophorone ________ _-____ 6 parts
thalene sulionate as a wet
mg agent_....'_ ____________ -__- g. perliteh- 0.3
'Diisobutyi ketone as a lifting
or less
Sodium ‘ditertiary butyl
Camphor as a lifting agent.--“ g. per liter-.. 0.8
Sodium ditertiary butyl naph
‘mixture 01f the eamphorand the wetting agent.
‘Example 1 1
Example 2
The use of alcohol-is optional. but when ad
ded, the‘purpose is to produce a homogeneous
was is no case large enough by itself to cause
sinking the canvas disc in less ‘than a matter or
hours. The wetting agent was su?lciently con
centrated to cause‘ sinking of the disc in an av
erage oi’ about 63 seconds. ,The temperature of
or less
isopropyl, etc)‘ _____ __v 4 parts __ l g. per liter
The concentration or the ketone lifting agent
Example 1_ ' ‘
nap thalene sultonate_ 5 parts __ 1 g. per liter
Camphor ___________ ....l_ lpart }
agent, made from an allryl naphthalene fraction
that had a boiling point of 185-195“ C. at 5 mm.
or less
Sodium ditertiary butyl
butyl naphthalene sulfonate, ‘as the wetting
Example 10
Seyferth and Morgan canvas disc wetting test on
alisolutions during the test was 25° C‘. ,
Sodium oleate ________ __ liparts __ 1g. per liter
conducted by the procedure Just above outlined.
v _
or less >
Example 9
n-amyl ketone ___________ .._ cc. per liter_ 1.25
1. A liquid, the surface activity of which has
Example 15
50% sodium oleate in methyl
n-amyl ketone ___________ __
been changed, comprising a solution of an alkyl
cc. per liter- 1.38
naphthalene sulfonate and a saturated aliphatic
ketone selected from the group consisting of
methyl-n-amyl ketone, diisobutyl ketone and
methyl-n-butyl ketone.
Example 16
30% sodium ditertiary butyl
naphthalene sulfonate from
2. A liquid, the surface activity of which has
been changed, comprising a solution of a sodium
alkyl naphthalene sulfonate and a saturated ali
a fraction boiling at 190
250" C. at 20 mm. in methyl
cc._perliter_ 1.55
10 phatic ketone selected from the group consisting
The addition of the ketone from 5-12 carbon
atoms to any surface active substance has an
effect on the activity of the latter which is con
been changed, comprising a solution of an alkyl
be exerted by calculation from the surface activ
n-amyl ketone ____ ___ _____ __
of methyl-n-amyl ketone, diisobutyl ketone and
methyl-n-butyl ketone.
3. Aliquid, the surface activity of which has
siderably greater than that which would normally 15 naphthalene sulfonate and methyl-n-amyl ke
4. A liquid, the surface activity of which‘has
ity of the separate components. The solutions of
been changed, comprising a solution of an alkyl
the mixture havean increased activity as regards
naphthalene sulfonate and diisobutyl ketone;
wetting, penetrating, detergent, frothing and dis
5. A liquid, the surface activity of which has
persing action. As speci?c examples which do 20
been changed, comprising a solution of an alkyl
not limit the scope of my invention, the surface
naphthalene sulfonate and methyl-n-butyl ke
active material may differ as widely as soaps,
sodium alkyl naphthalene sulfonates, and sodium
alkyl sulfates.
6. A liquid, the surface activity of which has
Other combinations which come within the 25 been changed, comprising a solution of a sodium
alkyl naphthalene sulfonate and methyl-n-amyl
scope of this invention are the combination of
my lifting agents with normal n-amyl ketone and
sodium di-amyl naphthalene sulfonate.
'7. A liquid, the surface activity of which has‘
been changed, comprising a solution of a sodium
Saturated Water solutions of ketones may also
be used alone for wetting purposes, and in this 30 alkyl naphthalene sulfonate and diisobutyl ke
use they may be employed not as lifting agents
8. A liquid, the surface activity of which has
in combination with a wetting agent, but as the
been changed, comprising a solution of a sodium
principal surface active agent. The preferred
alkyl naphthalene sulfonate and methyl-n-butyl
material for such purposes is a ketone having
from 5-12 carbon atoms, in the form of saturated 35 ketone.
water solutions.
I claim:
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