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Патент USA US3080291

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United States Patent
_
3,080,275
Patented Mar. 5, 1953
1
2
3,080,275
ature range employed for oxidation can be from ambient
temperatures to the re?ux temperatures of the alkylate
INSECT REPELLENT
Anthony G. Grady, Chicago, Joseph A. Verdol, Bolton,
and Russell W. 'Walker, Lansing, Ill., assignors, by
material employed when conducting the oxidation in the
‘liquid phase. Preferably the temperature is from about
50 to 200° C. If a vapor phase oxidation procedure is
employed, then the reaction is, of course, carried out
mesne assignments, to Sinclair Research, Inc., New
York, N.Y., a corporation of Delaware
above the boiling point of the alkylate feed and up to just
below the decomposition temperature of the feed or
product. The amount of oxygen employed in the oxida
No Drawing. Filed Feb. 8, 1961, Ser. No. 87,782
10 Claims. (Cl. 167-22)
The present invention relates to the repelling of in 10 tion scan conveniently range from about 0.05 to 1 s.c.f.,/
liter of hydrocarbon/hour and the reaction is. continued
sects by using certain oxidized petroleum derivatives.
for atleast about 2 up to about 100 or somewhat more
According to this invention, it has been found that an
hours, preferably about '20 to 40 ‘hours. Longer times
alkylate boiling primarily in the range of about 100 to
460° F. when oxidized with a free-oxygen-containing
can be used but do not seem to improve the product suf
tluoric acid or other mineral acids.
vide the oxidized alkylate with a peroxide number of at
gas, is a very effective insect repellent, particularly for 15 '?ciently.to justify the added expense and inconvenience.
‘The preferred manner .of producing the repellents of the
cockroaches.
present invention is by non-catalytic liquid phase oxida
The alkylate used in the present invention boils pri
tion of the alkylate materials. ,Catalytically oxidized alk
marily in the range of about 100° F. to 460° F. andgen
ylate is vfound to be less effective as a repellent than
erally has a boiling point spread of at least about 30° F.
and preferably at least about 70° F. The alkylate is pre 20 alkylate oxidized in the absence of a catalyst.
The extent of oxidation e?ected is preparing the repel
pared from an isobutane and a C3-C4 aliphatic mono
lent of ‘the present invention is measured by peroxide
ole?n hydrocarbon by treatment with a catalyst, for in
number. The non-catalytic oxidation is su?icient to pro
stance, an acidic material such as sulfuric acid, hydro
The products
produced by this alkylation process are essentially iso 25 least about 50, preferably at least about 200 or 400. No
reason has been found for carrying the oxidation past a
paraf?nic in structure and contain few, if any, ole?n and
peroxide number of about 600. In catalytic oxidation
aromatic components. The lower boiling components
the reaction is continued until a comparable amount of
‘produced by the alkylation process, e.g. those boiling pri
oxygen has been consumed or absorbed but a correspond
marily in the range of about 100° F. to 350° F. are wide
ly used in aviation fuels and premium automobile fuels, 30 ing increase in peroxide number may not be apparent.
If desired, the'oxidized alkylate of the present inven
and are marketed as “alkylate gasoline.” The “alkylate
tion may be caustic washed as, for instance, with dilute
solutions of alkali metal hydroxides to remove the foul
odor of the oxidized alkylate. Caustic washing has been
product, namely those boiling primarily in the range of, 35 found to give no detrimental effect to the repelling prop
erties of the oxidized alkylate of the present invention.
about 350° to 460° R, which are known in the petroleum
The following examples are included to further illus
industry as “odorless solvents.” “Odorlezs solvents” are
strate the present invention.
currently marketed in two grades diiferening mainly in
boiling range. The material marketed as odorless solvent
EXAMPLE I
light has an ASTM boiling range of about 345° F. to 40
Various
samples
of
commercial odorless solvent heavy
395° F. with a 50% point of about 360°'F. The odorless
were submitted for cockroach repellency tests. Odorless
solvent heavy has a boiling range of about 375 to 460°
solvent heavy is the fraction of the alkylate product of
F., and a 50% point of about 395° F. The ole?n con
isobutane and butylene which boils primarily in the range
tent of these products normally varies from about 1% to
10% and the total paraffin content is normally greater 45 of about 375 to 460° F. with a 50% point of about
395° F. The identity and results of the tests on the
.than about 90%.
samples are shown in Table I.
The oxidized alkylate product of the present invention
gasoline” fractions are suitable for use in preparing the
repellent of the present invention. It is preferred, how
ever, to employ the higher boiling fraction of the alkylate
Table I.-.-Identity of Odorless Solvent Samples In Cockroach Repellency Tests
Sample
Saponi- Peroxide Bromine
?cation ~ number number
number
Nature of odorless solvent heavy .
Unoxidized _______________________ __l___.__ _______________ _-_.
0
9. 5
0
0.6
5. 7
Unoxidizeduu. ________________________________ ___. ____ .V__V_
0 _
0.7
27. 0
Plirtign of O oxidized with oxygen at 100° 0. without 'cata-
28. 8
- Portion of A treated with Naleo HA alumina__
_
_
.vs -
PoBtggrboi C oxidized in presence of cobalt naphtheuate at
1
.
'
46. 1
.
382
81. 7
Odor
Relative
repel
lency
7. 7
12. 3
_ ‘
6. 6
Sweet pleasant“ Fair
_
_
.
Samples A and C were unoxidized alkylate a-s estab
material to oxidation with a free oxygen-containing gas. 65 lished by their low peroxide number.
Sample D was prepared by oxidizing a portion of
‘The alkylate may be converted by non-catalytic or cata
Sample
C as follows:
lytic oxidation of the alkylate in the liquid or vapor
Oxidation apparatus was set up and consisted of a
‘phase through intimate contact with a free oxygenecon
is obtained as aforementioned by subjecting thealkylate
taining gas. In general, the oxidation of the alkylate ma
terial .is__ carried out with molecular oxygen-containing
eases such. as air. pure. oxygen, or their. mixtures at
atmospheric. or superatmospherie pressures- The temper’
steam jacketed glass tube approximately 36" long and
1%” wide. The bottom of the tube was equipped with
;_a removable ‘Section ?tted with a 50/50 standard taper
joint containing ,a Eporous plate. Below the porous plate
8,080,225
3
d
there was located an inlet stopcock for the introduction
of oxygen and a second drain stopcock for removing the
product. The top of the reactor tube was ?tted to a
tory Chow was placed in the center of each test pan.
One hundred German cockroaches were introduced into
one pen and ?fty American cockroach nymphs were in
troduced into the other.
cold water condenser by means of a 24/40 standard
taper joint.
Controlled lighting was provided during the test period.
Cl
The reactor was charged with 500 grams of sample
From 6:00 am. to 6:00 p.111. each day the pen was
C and steam was introduced through the jacket until the
lighted by fluorescent lights suspended 18" above the
reaction temperature of 100° C. was attained. Oxygen
pen. From 6:00 pm. until 6:00 am. the pen was in
was then bubbled through the system at a rate of about
darkness and during this time the cockroaches would seek
0.3 ft?/hour. Oxidation was carried out for about 30 10 food and water. With the beginning of each light cycle
40 hours to obtain a product showing a peroxide num~
the cockroaches would seek refuge from the light in the
ber of about 382. The course of the oxidation reaction
shelter cartons, unless repelled by the treated linings.
could be followed by measuring the peroxide number of
The relative repellency of the various treatments was
samples of the reaction mixture taken over the reaction
‘determined by recording the number of cockroaches in
period.
15 habiting each shelter at 8:00 am. each day. Counts
Sample E was prepared adding 10 grams of cobalt
were facilitated ‘by removing the cartons from the test
naphthenate to 575 grams of sample C and the mixture
was heated to 165° C. Oxygen was passed through the
pen and immobilizing the cockroaches with CO2. A11
The resulting product showed the following properties:
peroxide No. 31.7; saponi?cation No. 46.1; bromine No.
cartons and cockroaches were returned to the test pan
after counting. Any dead or moribund insects were re
placed each day with fresh insects, ~
The results of these repellency test conducted over a.
6.5. The product had a sweet ester odor in contrast to
period of eight days are summarized in Table 11 below.
mixture at a rate of 0.5 ft.3/ hour for a period of 6 hours.
Table II.—Evaluati0n of Samples A~E for Repellency
Against American and German Cockroaches
[Average 1 percent of cockroaches]
American
Days after treatment inhabiting shelters-..
German
1
2
3
4
6
7
8
1
2
3
4
6
7
8
2O
28
20
2
2
: 22
12
28
18
2
4
6
52
22
16
20
8
12
20
10
18
16
14
4
30
0
64
16
6
2
0
56
30
10
2
0
18
0
0
2
70
6
8
8
2
4
44
24
6
4
11
3
19
30
18
13
1
12
2
25
27
21
16
l0
10
3
23
20
23
11
7
9
18
20
29
18
12
11
3
23
17
16
23
12
2
1
44
2
14
19
20
4
5
37
3
Sample, average percent:
Percent dead and moribund in test pan
Percent dead and moribund, total _________ __
8
0
32
1 Average of two replicate tests. 7
the material prepared by oxidation of odorless solvent
The data of Tables I and II establish that the unoxi
45 vdizecl alkylate showed little, if any, repellency towards
vheavy without catalyst (sample D).
The cockroach repellency tests were carried out ac
cording to the procedure described below.
Test insects: Adult male German cockroach,.Blatella
germanica (L). Thirteen-week-old American cock
roach nymphs, Periplaneta americana (L).
Test pan: The test pan consisted of a 40" x 24" x 8"
stainless steel open top box, partitioned in the center
cockroaches whereas oxidized samples of this material
were effective as repellents. The data also demonstrate
‘that the oxidized alkylate was much more elfective when
oxidized in the absence of a catalyst than when oxidized
catalytic’ally.
’
EXAMPLE II
to form two 20” x 24" pans. Petrolatum was appliedv
Oxidized alkylate was prepared both by oxidation in
to the walls of the pen to prevent the escape of the 55 the absence of catalyst (sample F) and in the presence
test insects.
‘
of a cobalt naphthenate catalyst (sample G) in accord;
Test shelter: One-half pint ice cream type cardboard con
ance with the general method of Example I and subd
tainers the bottom section ‘of which were lined with
mitted to cockroach repellency tests. The alkylate oxii
treated 15 cm. No. 2 ?lter papers and the lid section
dized was prepared from isobutane and butene and boiled
with 9 cm. No. 2 ?lter paper and an entry hole through
primarily in the range of 375 to 460° F. with a 50%
60
the wall and lining of each carton was provided in the
point of about 395 ° F. and is known as odorless solvent
base.
heavy. For comparative purposes. a commercial repel
lent designated as X at 1% concentration in base oil
Procedure.—-The test samples were applied to the ?lter
(sample H) and a 2% concentrate of fatty acids ex
paper shelter liners by pipetting 1.3 ml. of each onto
the 15 cm. discs and 0.5 ml. onto 9 cm. discs while on 65 tracted from alkylate in the same base oil were also
tested. The fatty extract of oxidized alkylate was pre
glass plates. When the ?lter paper had dried to touch,
pared by treating the oxidized inaterial with dilute NaOH
‘they were pressed into the bottom and lid sections of
and acidifying the aqueous alkali extract. The extract
the cardboard cartons to form a continuous treated in
was washed with ether and the ether evaporated. The
terior surface lining. ‘Four cartons were prepared for
each test sample, two of which were used in tests con 70 resulting acid residue was blended into the base oil at
a concentration of 2%. The 2% concentrate showed
ducted with German cockroaches and two with American
a peroxide No. of 3.2, sap. No. of 5.9 and bromine No.
cockroaches.
The duplicate test shelters of each treatment were
32.3. The material had a foul odor and was desig
placed on the floor of the respective pans in random
nated sample I. A summary of materials submitted for
fashion. Water and food in the form of. Purina Labora- 75' testing and the results are presented in TableIiI.
‘
atal,:o.so;27‘s
5
_
.6
. ‘Table 1II.—Identity of Odorless Solvent‘ Samplesfand’.
Commercial Repellent ‘Submitted for Cockroach Re
pellency Tests
' 'Saponi?;
Sample
Identity of sample
‘
cation
Peroxide Bromine
number
number
number
Odor
Relativev
" repellency
F _____ _. Odorless solvent heavy oxidized without catalyst at 100° C. for 80
hours _________________________________________________________ ._ ‘48. 5;...
v293
7. 7 ‘Foul-.__ ‘Good;
G _____ ._ Odorless solvent heavy oxidized with cobalt naphthenatc catalyst
at 165° C. for 6 hours __________________________________________ -. 50. 0_____
‘H _____ _.
Commercial repellent at 1%‘cone. in base'oil 1 . _ _ . . _ _ .
'37. 1'
__.__
I. _____ __ A 2% concentrate of fatty acids (which were extracted from
- 1
oxidized odorless solvent heavy) base oil _______________________ -.
5. 9 ____ ._
3. 2 p
1 2,3,4,obis-butylenc tetrahydrofurfural, a condensation product of iuriural andbutadiene.
The procedure employed for the second series'of re- 12¢ less'solvency heavy of Exa-mple'II' (sample-F). A 2%
pellency tests was essentially ‘the same as described pre‘ viously for the ?rst series of tests, excepting that the
concentrate ofcornrnerci-eil repelIentjX' v(sample J) was
also tested. The identity of- the materials tested-and the
?lter papers wetted'with the test samples were ‘permitted
a to dry for 24 hours. This modi?cation was'made to re
. results .are summarized 'inffl‘able ‘ V,_
duce the mortality rate, since the earlier test indicated..25
that the high mortality rate might be due to the presence
of highly volatile material in the test samples.
“Table -V___Idemity»0f Experimental Samples for. cock_
Four'
ma h Re éllenc .Tet
hundred adult male German cockroaches, Blatella ger-
manica (L) ‘were used in the test pan.
'
'
“
moribund cockroaches were replaced each day with fresh‘ 30 "
insects. Results of these testsare shown in Table IV.
' 'Sam-
It should be noted that Table IV also includes a test
'
91°
‘ '
_ 21 days.
‘H
?
ThlS separate test was run for the purpose 35 J
'Idenmyofsample
‘numben
a
‘Relative
0d”
{511132;
"
>
'
293 :Foul ____ “Lewd.
wheglcvy‘gseeT?ble III).
H
t
‘P
K'III 37y; d$€é?gi;?hdt§1"?é;8; ---- "@266- __'_3§f‘f?_~_: ‘£2:
This separate ‘test
L
clearly established that the oxidized odorless solvent
'- heavy sample F was superior to sample H.
'
$.Peroxlde _
F ____ __ ‘Oxidized odorless solvent
>_ of directly comparing the repellency ofpxidized odor'
y
-
The age of this shelter treatment was
less solvent heavy with "sample H.
p
‘
exposure of four shelters each of samples F, H and'un-
--treated shelters.
c
Any dead. or
2 71%; m basoho?d
f_""'
Y
_d
466
d
D
-m9;§;§3§‘1‘? y mpemn e
f" O """ "
‘0'
jM--.-- 11557? d;g,?alrimgth.vlgéxane#
"448 --Ldo__--‘--_
~190
‘The data of Tables. III and vIV demonstrate that the I‘ 40'
7i?g.i_ggse°gfgiiisem%>
non-catalytically oxidized odorless solvent heavy was
"
?isooetenylmlcvhol!
superior to the commercial'repellent X when the com-
' '
_ mercial repellent was tested at a 1% concentration in
'
‘
‘
.
V
_1'Isooctenyl_alcohol'was"added'tmsoluhilize'2;5-dimethylhexane-2,5
base oil (sample H). The sample containing fatty ‘acids
‘dlhydmpemx‘de'
Table IV.—Evaluation of Samples F~I and aCommer
cial Repellent H for Repellency Against German
Cockroaches
[Average 1 percent inhabiting shelters]
Days after treatment ........ ..
2
3
4
5
6
7
8
15
21
Sample
F _______________________ __
0
7.8
6.5
4.5
5.3
as
6.0
G._
H__
._
__
1.3
6.0
10.5
29.7
10.8
23.0
16.5
27.2
11.7
27.3
19.5
33.2
30.3
25.3
25.8
32.0
I ................. _.
..
81.5
39.5
24.7
27.3
25.0
22.0
22.7
32.7
Free roviugin test pan
___ 11.2
Percent mortality? ......... .. 0.3
12.5
6.5
35.0
2.3
24.5
5.5
30.7 21.5
4.5
4.3
15.7
7.8
7.5
2.0
1 Average is of four replicate tests.
2.0‘
‘
2 The majority or the observed mortality was fonndto be in shelters treated with'F.
derived from‘ the oxidized odorless solvent heavy proved
ineffective as a repellent and indicated that the foul odor
The procedure used for meeting-(these "samples 1was es~
sentially identical with the procedure‘ already‘ described.
of oxidized odorless solvent was not responsible for its 70 The test was divided into twov parts, ‘Part vI; consisted of
repellcncy.
a four replicate test with ‘samples F and I, using 250
EXAMPLE ' HI
;,adult.male’ German cockroaches;Blatellagerinarticlz, ‘.(f) .
Various peroxides as concentrates in'lbase oil (samples
Part II consisted :of .a‘twomeplicate test with'samples‘l
‘K, .LQM) were submitted to the cockroach repellency
through M, using .250 vGerman cockroaches‘. ‘The results
testsnot Example I_ and'compared tother'oxidized o'dor- 75 of- these testsare'fsummar-iz'ediinTablc‘VI.
18,086,276
"7
Table VL-Evaluation of Oxidized Odorless Solvent
Table VIlI.-—Evaluation of Oxidized Odorless Solvent
Heavy and Related Materials for Repellency Against
‘Heavy and Related Materials for Repellency Against
German Cockroaches
German Cockroaches
[Average Percent Inhablting Shelters]
{Average percent inhabiting shelters]
5
Part I (avg. of 4 reps.)
Test N0. 1
Days after treatment
Days after treatment ................. -_
2
3
4
5
6
7
3
2
13
74
29
47
17
41
12
so
19
52
16
47
.7 ____________________________ -.
0___
-
13
24
42
38
29
37
P ..... --
0
4
l6
12
17
9*
p
Free roving._--
Percent mortality
Part II (avg 0(2 reps.)
10
3
4
5
6
8
9
15
Sample
2
0
51
1
4o
9
29
24
21
27
17
24
1o
1s
17
19
_ 1s
10
17
19
22
25
26
24
0
2
3
2
6
10
19
s
9
Percent mortality _______________ ._
1
"15
Test No. 2
Days after treatment
Days after treatment ................. --
2
3
am?-i ______________________________ __ 74
S
4
5
6
7
8
2
l :
a
4
s
s
15
Sample
K_
L_
35
16
20
16
22
14
9
11
15
21
20
17
19
17
19
22
16
M__
- 12 20
I1‘ ___________________________ __
0
4
g
7
1g
4
g
5
_ _ _ . _ __
_ _ _ _ _ __
0
7s
s
65
5
so
17
49
13
41
s
4s
s
47
14
46
Percent mortality _______________ __
0
0
1
s
s
10
13
.
‘
19"
17
0
22
29
24
25
14
15
Free roving_.__
2
17
14
20
22
25
37
Percent mortality ____________________ _-
0
O
0
l0
5
9
8
N_ _.._
Q . _ . __ . _
.
29
'
Test No. 1 (Table VIII) indicated that the oxldlzed
Tables V and VI show that the odorless solvent heavy v 25 propylene tetramm- and reformate showed some repep
non-catalYzed oxidation) was superwr ‘0 thehommeflenc y for the ?rst ?ve days, but after that time
sample
a
. .
cial repellent X when the latter was employed at 24’
J shower greater repellency.
concentration (more than the recommended concentra-
Thus, these oxldlzed pe
. troleum stocks do not appear to be egective repellents
tion for commercial me)- The tests also Show that
in comparison with oxidized odorless solvent.
tertiary alkyl peroxides and aryl peroxides were me?ec- 30 Test No. 2 (Table VIII) showed that oxidized odor
five repellents, Suggesting thahlf PeI‘OXIde were I'BSPQIIless solvent and the caustic washed oxidized odorless
Sible for the repellent Properhes 0f the OXldlZed alkylate
solvent were both good repellents. This further demon
lhey were more likely peroxides of a Speci?c Structure
strates that the acidic components, which presumably
derived from the alkylate and not any PefOXide Selected
were responsible for the foul odor of oxidized odorless
randomly. There is also the posslblllty that other oxy- 35 solventheavy, were not active Iepe1lents_
genated compounds contribute to repellency.
I
The test sample Q containing isooctyl aldehyde and
EXAMPLE IV
cumene hydroperoxide did not show any repellency what
.
soever.
_
_
Therefore, no advantageous sheet was realized
-Yafl0118 Samples ldenh?ed "1 Table VII below W?”
by adding aldehyde to cumene hydroperoxide since earlier
sllhlected t0 the FOPkIOaCh repellency test- In P1'@Pa1"1ng -' 40 tests in Table VI showed that cumene hydroperoxide
sample N an oxldlzed odorless solvent heavy havlng an
P51- 85 was ineffective.
.l?ltlal peroxlde No. of 226 washed twice wlth equlvolume
EXAMPLE V
portions of 5% NaOH and then with water. The result-
7
ing product had a sweet, pleasant odor, and showed a
Samples identified in Table IV below were subjected
PefOXldB number of 109. Samples 0 and P were pro‘- 45 to the cockroach repellency test described in Example I.
pared by the non-catalytic oxldatlon procedure describe
__
in Example I. For comparison, the test on oxidized
.
.
Table IX‘ Identity 225312‘;Ices ggsbtgmtted for cockroach
odorless solvent F and the commercial repellent X, 2%
cone. in base oil (I) are also included.
p
The results are
.
.
also Summanzed
m
Table VII‘
y
_
s
50 Sample
'
Identity
Table VII.—-Identity of Experimental Sample for Cockroa h Re ellenc
c
Sample
p
Tests
Peroxide
R ____ _. Odorless solvent heavy oxi-
Odor
Relative
.
_
repeuency 50
Foul """" " Good’
s
____ -_
lyst (see Table III).
heavy, whichwascaus-
109
Sweet
U
Good.
pleasant.
>60
gi‘tittreafgesld 2358310013:
elative
repel
“my
58.1
425
12
1o . 6
Good.
_
67
Fan‘.
102 . 5
P oor.
575 Pleasant““" Poor‘
ess so ven
402
65
Foul ------ “
Do'
466 "'"do """ "
D0’
I ‘ hours without catalyst‘
Q ---- -- 2175x065??? balgdfgi
-1-°I§m11]-)-
,
223
d
so Ven-d eavsg OZ;
16%‘? .‘éhpergxl
t6 {11121; "0
W"... Causticvi'ashtedloxidized 050;
'
P '''' ” Plhiligrllegi ltgllgagmlf‘ozgélll
odo?
''' "
10
F k
'
1
a '
17.0
237
Good.
18.7
50
D0.
675
Poor.
veltlt
léeavybmxidized
With
0" 0a a YS
.
_
7;‘ hours
without cata-'_
'
envy, w ie
avast
treated gith< KIi t‘;
es roy peroxi es oriq no
peroxide number was about
3olzazlzfte5
oxidatlon without
C81
ys
.
Y ____ -- odorless solvent heavy oxi-
plus'1% isc-octyl aldehyde
2 .
ple diluted to 207
by volume in odorless solz
V.... .- causti‘ovlwazllllegaoadoyrsles‘s sol~
,
O "" " ogg?‘dlilzighftmlggl°gm?g?
-
R
fjglé‘?Q“ 0/12 mm‘
Oxidizedodorlesssolvent,
8c. Yacl ,p XY
Aggxxégenuumlero
ation of odorloess solvent
1 _____ _- 2%Xln base oil ................................ -_ Fair.
N ____ -.
d
eroxi e
number
dizedy‘vithoutI cataflizsg to a
ear on 0
arm d on dit‘ll
s l n'r .... __ Hvelltmimiii"
v
293
P
-
number
F --- '" ogi‘ijgliez?isgi‘?elggthggg
eatlon
number
y
Identity otsanlple
a
aponi -
70
dlzed with cobalt naphthe
.
nateeatalystplus5%t-butyl
.
v
70
perbenzoate.
The test procedure was the same as already described.
Two separate tests, three replicates each, were conducted
7
The tests were conducted in the same manner as de~
LusinmZSO adult male German cockroaches Blatzella
scribed in Example I. The test was broken down into
ermanica (L). ._ The results ofthese tests are resented
two parts with 250 cockroaches belng
used in each
art
$
..
_
_
P
m Table VIII.
75 of the test. The results are summarized 1n Table X.
.
,a
.
-
.
s
,
I
I
-
-
3,080,275
10
9
Table X .-—Summary of Cockroach Repellency Tests
[Average percent inhabiting shelters]
Part I
Days after treatment
2
Shelter treatment:
R ......................... .._
3
O
4
0
5
2
6
0
7
7
8
2
9
2
1
10
1
14 Avg. per
cent'day
2
1. 21
0
78
0
10
66
14
19
16
11
24
19
21
19
26
20
5
23
7
22
24
19
13
25
20
24
31
16
39
20
23
12. 5
23. 4
10.9
Percent tree roving ____________ __ 22
10
52
36
28
63
33
41
28
16
23. 4
1
1
1
5
41
14
17
12
0
6. 8
8
9
10
14 Avg. per
Percent dead and moribund_.-__
3
Part II
Days alter treatment
Shelter
V. treatment:
2
_ -
3
4
5
6
7
cent/day
0
0
3
5
11
3
6
25
1
3
1 4.05
‘V.
_ 0
_ 31
Percent free roving ____________ -_ 69
7
77
16
13
42
42
27
52
16
29
34
26
4
22
71
9
38
47
8
20
47
1
17
81
6
45
46
7. 43
27. 0
33. 0
3
1
0
4
32
17
21
17
0
7. 05
Percent dead and moribund_-_-_
4
According to the results summarized in part I above,
the oxidized odorless solvent heavy (R) was almost com
pletely effective as a repellent. The odorless solvent sam
ple diluted to 20% concentration by volume (S) and the
odorless solvent sample oxidized to a peroxide number of
only 101 (U) were about equal in repellency, but were not
as effective as the undiluted sample R.
The heart out
intimate contact with an oxidizing free oxygen-containing
gas for a time to absorb suf?cient oxygen to provide said
alkylate product with a peroxide number at least about 50
30 up to about 600 under non-catalytic oxidation conditions,
said time being up to about 100 hours.
2. The product produced by the method of claim 1.
3. The method of claim 1 wherein the oxidation is
conducted in the liquid phase and in the absence of an
obtained by distillation of odorless solvent heavy T 35
oxidation catalyst.
showed poor repellency. Thus in general the active in
4. The method of claim 3 wherein the alkylate product
gredient or ingredients were concentrated in the lower
boiling components of the oxidized odorless solvent, espe
cially since the higher boiling concentrate, as indicated,
showed poor repellency.
Part II of the test presented in Table X above was de
signed in order to further evaluate the repellency oxidized
odorless solvent, which was caustic treated to destroy the
free acids and treated with potassium iodide to destroy
most of the peroxides. The test showed that the caustic
washed oxidized odorless solvent heavy V and the caustic
washed sample which also had the majority of the per
oxides removed (W) were almost equal in repellency.
has a boiling range of about 350 to 460° F.
5. A method of claim 3 wherein the oxidation is con
ducted for a time su?‘icient to provide the alkylate pro
40 duced with a peroxide number of at least about 200.
6. The product produced by the method of claim 5.
7. The method of claim 5 wherein the temperature of
oxidation is about 50 to 200° C.
8. A method for repelling cockroaches from an area
subject to cockroach encroachment which consists essen
tially of applying to said area the product produced by
the method of claim 1.
9. A method for repelling cockroaches from an area
Sample Y was included in the test in order to ascertain
subject to cockroach encroachment which consists essen
whether or not a sample of odorless solvent heavy, which 50 tially of applying to said area the product produced by
was oxidized with cobalt naphthenate catalyst, and which
previously showed little repellency, could be made more
repellent by the addition of an alkyl perester. The test
results, however, indicated that this sample showed poor
the method of claim 3.
10. A method for repelling cockroaches from an area
subject to cockroach encroachment which consists essen
tially of applying to said area the product produced by
repellency.
55 the method of claim 5.
We claim:
References Cited in the ?le of this patent
1. A method for producing a cockroach repellent which
comprises oxidizing the alkylate product of isobutane and
UNITED STATES PATENTS
a C3-C4 aliphatic monoole?n, said alkylate product boil
ing primarily in the range of about 100 to 460° F. through
2,020,648
Hyman ______________ __ Nov. 12, 1935
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