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Патент USA US2110074

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Patented Marti, 193.78
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Luther Bishop Arnold, Jr., Wilmington, DeL, as-l' '
signer ‘to E. I. du Pont de‘ Nemours & Com‘
pany, Wilmington, Del., a corporation of .
No Drawing. Application July 12,
Serial No. 31,041
1935, '‘
v1'0 Claims v(o1. 167-31)
This invention relates to an improved type of
‘proper acidity may be determined by making the '
product acid to methyl red indicator and alkaline
for usein treating textile ?bers.‘ More particu ‘to Congo red indicator.
larly, the invention relates to the preparation of
An alternative method is to use orthophenyl
5 a stable solution of ‘improved wetting properties phenol instead of sodium orthophenyl‘phenate.
- wetting agent with' mildew-proo?ng properties
consisting of a wetting agent, a fungicide which
has an assistant action on the wetting agent and
‘ water-soluble organic solvents in water.
more particularly, the invention relates’to the
preparation of a stable solution of an alkyl naph
, thalene sodium sulfonate, an orthophenyl phenol
derivative and water-soluble organic solvents in
f This invention has as an object the preparation
15 of a liquid product with the combined properties
of a wetting agent and a fungicide wherein the ,
fungicide has a pronounced assistant action on
In this case, the isopropyl naphthalene sodium
i i.
sulfonate is dissolved in water as above, and 2.2 ‘
parts of orthophenyl phenol are dissolved in the
above mixture of ethyl alcohol and ethylene
chlorhydrin. The two solutions are then mixed
together, the mixture ?ltered, and the pH ad-_
justed if
The product, as formulated above, may be
cooled to 8-10° C. without becomingcloudy or
separating into layers.
The fungicide, orthophenyl phenol, in the
product as formulated‘above,‘ has a decided as
the surface active properties of the wetting agent. ~ sistant action on the sodium isopropyl naphtha
A further object is to prepare this product in such
lene sulionate wetting agent.f._
, -
a manner that it ‘will be .readily dispersible in ' -_ The sodium» isopropyl naphthalene- ‘sulfonate 20
water and will be stable'under normal storage " wasfound to be 25% more e?icient inv the pres
conditions. A still further object is to ‘employ
this product for treating textile materials in
ence of 20% of its weight of'orthophenyl phenol
than alone as determined by the Draves and :
order to prevent mildew growth thereupon. ,Clarkson wetting out test .(Am. Dyestufl’ Rep. 20,
Other objects'will appear hereinafter.
201 ,(1931) ). Sodium orthophenylfphenate is of
The aforementioned objects of ‘this invention _’ equivalent effectiveness in improving: the wetting
are preferably accomplished by preparing a con
action of the sodium isopropyl naphthalene sul
centrated solution of an isopropyl naphthalene ?fonate. Thus, this combination‘ of a ' wetting
agent and a fungicide is unique in that thefungi
sodium sulfonate and a sodium salt’of an ortho
phenyl phenol derivative. To this‘ solution is
cide has the additional property of assisting the
added one or more water-soluble organic solvents
' and the solution is acidi?ed under controlled con
‘ wetting agent. Sodium orthophenyl phenate has
no wetting action whatsoever as determined by
This invention involves the preparation of a
concentrated solution of an isopropyl naphtha-a
lene sodium sulfonate wetting agent and a sodi
um orthophenyl phenate fungicide. To this is
added a mixture of ethyl alcohol and ethylene
chlorhydrin. The product is then preferably
The purpose of the solvents is to dis
, the Braves and Clarkson test. Other fungicides
were found either with relatively very little or '
without any assistant action on the wetting prop
erties of the sodium isopropyl naphthalene ‘sul
fonate. Other fungicides which were investi
gated included sodium tet'rachlor phenate, tetra
chlorphenol, sodium chlor-ortho-phenyl phenate, I and chlor-ortho-phenyl phenol. They were with
solve the water insoluble orthophenyl phenol,
very little assistant action on the'wetting agent.‘
The product may also be .?nished with an
and to prevent the precipitation of both the iso
alkaline reaction instead of with an acid reac
propyl naphthalene sodium sulfonate wetting tion. This is accomplished by. mixing the com
' agent, and the orthophenyl phenol fungicide ponents, as in the ?rst example above, without
when the product is cooled to 8-10° C.
‘acidifying the ?nal mixture. The sodium ortho
The preferred method of preparing the product phenyl phenate hydrolyzes to make the product
is as follows: 10.0 parts of isopropyl naphthalene alkaline. The product in this form is not as sta
sodium sulfonate and 2.5 parts of sodium ortho " ble to low temperatures as when prepared by
phenyl phenate are dissolved by heating in 71.5 the preferred method, but it is‘. more suitable
parts of water. To this is added 6.0 parts of where an acid product may be harmful. to the
ethylene chlo'rhydrin and 10.0 parts of commer
shade of dyestuffs or to the ?ber. ' ' .
which is formed on acidi?cation of the product,
cial ethyl alcohol. ' The mixture is ?ltered to reIn place of isopropyl naphthalene sodium sul
move insoluble impurities and acidi?ed to‘ pH‘ fonate other alkyl naphthalene. sulfonic acids '
3-6 by the addition-of hydrochloric acid. The and their alkali metal salts maybe used. For > 55
instance, the employment of Ibutyl naphthalene
sulfonic acid and its alkali metal salts,.dibutyl
naphthalene sulfonic acid and its alkali metal
salts and di-isopropyl naphthalene sulfonic acid
ts‘lfalkali metal salts is contemplated.
Cl .an
I, ep'ifoduct of this invention-in either of the
above ?nal forms is aivery effective wetting agent
and fungicide when applied to‘textiles in as low
concentrations as 0.5—'1.0%. .It is particularly
10' effective for wetting outvover-rdried cotton raw
stock after machine dyeing and ‘for conditioning
cotton yarn before .wetjtwisting. vThe :fungicide
prevents the growth'o'fv mildew on the moistened
cotton during storage'for'longperiods of time.
The product is also-suitable for-wetting out
or conditioningany type of textile ?ber whether
as rawstock, yarn, or fabrichparticularly where
the moisture is applied by spraying and where
it is desirable to protect‘lthe textile material tem
20 por-arily against the growth of mildew. The prod~
isopropyllnaphthalene sodium sulfonate. ortho- '
phenyl phenol ‘or an alkali metal phenate de
rived therefrom, ethylene chlorhydrin, and ethyl
5. A fungicide and wetting agent composition
suitable for mildew-‘proo?ng organica?brous ma
terials comprising 10 parts of isopropyl naphtha
lene sodium sulfonate,‘2.5 parts of sodium ortho
phenyl phenate, 71.5 parts of water, 6 parts of
ethylene chlorhydrin, and‘lO parts of ethyl alco 10
hol adjusted’ to a pH between 3 and 6.
‘ 6. The'process of makingthe composition'de
?ned inthe preceding claim which comprises dis
solving 10- parts of isopropyl naphthalene so
dium sulfonate- and 2.5 parts ofsodium ortho
phenyl phenate by heating in 71.5 parts of water,
adding 6 parts of ethylene chlorhydrin and 10
parts of ethyl alcohol, ?ltering the mixture to
remove insoluble impurities, ‘and acidifying the
mixture to obtain-a pH between 3 and 6.
v7. A fungicide and wetting agent composition
for mildew-proo?ng organic ?brous ma
concentrations of 0.5-l'.0% in water.
, .
terials comprising 10 parts of ‘isopropyl naphtha
As many apparentlywidelydifferent embodi
sodium sulfonate,.2.2 parts of orthophenyl
ments of this invention »may be made without lene
phenol, ‘71.5,parts of water, 6parts of ethylene 25
IO CA “widely departing from the spirit and scope there
of, it is to be understood that the invention is " chlorhydrin, and lOparts of ethyl‘ alcohol.
8. Theprocess of making the composition de
, not limited to the specific embodiments thereof
not is recommendedgfor application by spray at
except as de?ned in the appended claims.
- I claim:
_ -
V l. A fungicide and wetting agent composition
suitable for mildew-proo?ng organic ?brous ma
terials comprising an aqueous solution contain
ing an alkyl' naphthalene sulfonic acid or an
; alkali metal salt thereof and orthophenyl phenol
or an alkali metal phenate derived therefrom.
.2. A fungicide andvwetting'agent composition
?ned in the preceding claim which comprises
dissolvingv 2.2 parts of orthophenyl phenol in 6
parts of ethylene chlorhydrin and '10 parts of 30
ethyl alcohol, mixing said solution with one con
taininglO parts of isopropyl naphthalene sodium
sulfonate and 71.5 parts of water, and ?ltering
‘9. A concentrated aqueous solutionsuitable for 35
use inthe mildew-proo?ng of organic ?brous ma
terials containing a wetting vagent, a fungicide
which is not a wetting agent‘butwhich has the
_ an alkyl naphthalene sulionic acid Oran alkali property of increasing the wetting power of said
wetting agent to a marked degree, and suf?cient 40
40 metal salt thereof, orthophenyl phenol or an al- _
chlorhydrin to prevent separation of
kali metal phenate derived therefrom, and a
said wetting agent ‘or fungicide" from ‘said solu
water soluble organic solvent.
_ 3..A fungicide and wetting agent‘ composition I tion at 10° C., said wetting agent being isopropyl
naphthalene sodium sulfonate, and said fungicide
suitable for mildew-proo?ng organic ?brous ma
terials comprising an aqueous'solution containing being orthophenyl phenol or any alkali metal 45
an isopropyl naphthalene sodiunr sulfonate, . phenate derived therefrom.
10. Mildew-proof organic ' ?brous materials
orthophenyl phenol or an alkali metal phenate
suitable for mildew-proo?ng organic ?brous ma
terials comprising an aqueous solution containing
»,-.clerived therefromfand a water soluble organic
solvent. '_
4. A fungicide and wetting agent composition
suitable for mildew-proo?ng organic ?brous ma;
terials comprising an aqueous solution containing
containing orthophenyl phenol or an alkali metal
phenate derived therefrom and isopropyl naph
thalene sodium sulfonate. .
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