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Патент USA US2134001

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Patented 0'... 25, ‘1938
. UNITED STATES » PAT:
2.134.001
Momnoomm- mm.‘
_
t.
v.
.
_
N
Lindley
pany,
Mich.,E.
Midland,
assignors
Mills and
Mich.,
toWilliam
The
a corporation
Dow
w. Ohemical"Com-'
Allen, of
Midland,_Michi- '-: - _ "" ' ;
gan
, No Drawing. Serial
Application
No. 169,470
October-v16, 1.4937,:v
1 _ ' -
6 Claims. (Q1. 21-5)
This invention relates to the'protection of fur, mothproo?ng of woolen- fabrics and the like, the
hair, feathers, wool, etc., against the attack of articles so treated are not stained or attacked
moths. It is more particularly concerned with ' thereby orcaused todevelop any distinctive odor.
the mothproo?ng of fabrics.
_
‘Furthermore, these aryloxy alkylols are not ap-,
Some agents heretofore employed for moth
preciably dissipated from the fabric impregnated 5
proo?ng are capable of attacking or staining the therewith by contacting such fabric with water,
treated material. Other mothproo?ng products ‘ soap solutions, or petroleum distillate dry-clean
are highly volatile and impermanent in nature ing ?uids, or by volatilization or ‘sublimation, of
and are soon dissipated by vaporization from the
10 material to which they are applied. Temporary
protection has also been afforded by compounds
which are soluble in water or soap solutions.‘
the compound.
'
.
,
.
The aryloxy alkylols are, for the most part, 10
odorless, water-white, viscous likuids. These
compounds may he prepared by reacting a suit
Some protecting agents such as the phenols and ' able phenol with a halo alcohol,v e. g., ethylene
mercury and ?uorine compounds are irritating bromohydrin, propylene chlorhydrin, mono-~
15 to the skin and poisonous to human beings, while > chlorobutanol, etc.,- in the presence of a suitable 15
other common organic derivatives are objection
alkali, e. g., NaOH, KOH, etc. 'I'hesecompounds'
able because of their characteristic odor. A fur
may be dissolved in suitable solventsv inamounts ,
ther disadvantage in the use of many of the com
ranging between 1.0 and l0per cent by weight '
mon mothproo?ng compositions is the fact that thereof and advantageously employed as- moth-g
20 the residues deposited in the treated article fol
proo?ng compositions. ' We have ‘found that so- 20
lowing evaporation of liquid constituents are lutions containing between about 3 and about 7-5. '_ ,
crystalline and are soon dusted out of material per cent by weight of such compounds'are‘satis
treated therewith.
Among the objects of this invention is to pro
25 vide a method for the protection of the afore
mentioned materials which will (1) give rela
tively permanent protection therefor against at
tack by moths, and (2) yield a protected product
free from objectionable odor and toxicity to hu
so mans. Another object is to provide a vcomposi
tion comprising a volatile organic solvent having
dissolved therein a mothproo?ng material which
upon application to material susceptible to attack
will prevent destruction thereof by moths without
85 at the same time staining or otherwise injuring
the material.
‘‘
We have discovered that the foregoing advan
tages can be obtained by employing as mothproof
ing agents aryloxy alkylols having the formula
40
factory.
I
-
_,
'
In the numerous tests carried out‘toe'stablish '
the utility of the aryloxy alkylols as mothproof- >25
ing agents, the larvae of the black carpet beetle
(Attagenus piceus) were employed.
This insect >
is a common household pest attacking woolens,
furs, and other materials' It is particularly de
structive to fabrics used in upholstered furniture 30
and to woolen carpets and rugs. It is more resist
ant and harder to control than the common case'
making clothes moth or tapestry moth, and con-'
centrations of ‘ material found suitable for its
control on fabrics have been shown to be more
_ than adequate for the control of the latter species.
The following examples are illustrative of cer
tain modes in which our invention may be. ap
plied, but are not to be construed as limiting the
same.
'
40
Example 1
A‘number of samples of‘ white wool mohair],
cloth were saturated with solutions of 4-tertiary- >
butyl phenoxy ethanol in a volatile, highly refined
petroleum distillate, thereafter pressed to remove 45 .
wherein R represents an alkyl residue and X rep
resents a hydrocarbon substituent containing at
least 4 carbon atoms and selected from the group
consisting of the alkyl and cycloalkyl radicals.
50 When compounds of the above class, or. mixtures
thereof, are incorporated with a suitable organic
solvent and particularly with a lower aliphatic
alcohol, a liquid chlorinated hydrocarbon, or a
volatile, highly re?ned petroleum fraction, and
the solution so formed thereafter employed in the
excesses of the treating ?uid, and allowed to dry.
On each of a number of these samples ?ve larvae
of the black carpet beetle were placed and the
sample‘ folded over the larvae. .These infested
cloth samples were placed in a closed ‘cardboard 50 ’
box and examined from time to time to determine
the amount of feeding or other attack directly
attributable to the beetle larvae. Simultaneous
tests were made with larvae upon untreated sam
ples of the mohair, both control and test samples 55
"
2,134,001
2
being thereafter incubated at temperatures of
85°-90° F. and at a ‘relative humidity of 70-75
per cent. Examination of incubated samples
impregnated with a 3 per cent 4-tertiary-butyl
phenoxy ethanol solution showed that after three
Other solvents for the aryloxy alblols, form-,
ing solutions which may be employed as dry
cleaning agents, are liquid halogenated hydrocar
bon compounds such as carbon tetrachloride,
chloroform, ethylene chloride, trichloro-ethylene,
the impregnated samples. In the case of the
samples originally impregnated with a 5 per cent
solution of the treating compound, there was no‘
feeding by the larvae after three weeks incuba
chlorobenzene, and the like; hydrocarbon com
pounds, such as benzene, the lower paramn hy
drocarbons, toluene, and the like; and the alco
hols, such as ethyl and methyl alcohol, etc. Per,
fumes, coloring agents, and the like, may be in 10
corporated in the mothproo?ng ?uid, if desired.
tion and an average of between 2 and 3 of the lar
vae were'dead on each test sample. The un
in a water-immiscible solvent, such composition
weeks there had been no feeding by the larvae.
An average of two larvae were dead on each of
When the aryloxy alkylcl compound is dissolved
treated controls showed a slight feeding by the , may be employed as an emulsion with a soap or
other wetting or emulsifying agent and water. 15
Any
of the cleansing agents and detergents com
two weeks, and heavy feeding at the end of three
weeks incubation. Tests carried out over the mon to‘ the cleaning art may then be employed
same period upon mohair treated by immersion in conjunction therewith.
We claim:
in the petroleum distillate alone showed moderate
1. A process for mothproo?ng woolen fabrics
20 feeding by the larvae after one week, moderate ‘ and other materials subject to attack by moths
feeding after two weeks, and heavy feeding at‘
which comprises treating such material with an
the end of a three-week period.
15 larvae after one week, moderate feeding after
Example 2
26
aryloxy alkylol compound having the formula
' Samples of the impregnated mohair described
in the foregoing example were thoroughly dried
and subsequently immersed and well- washed in
an excess of a common-home dry-cleaning ?uid.
These samples were thereafter dried andexposed
to carpet beetle larvae as described in Example 1. wherein R represents an alkyl residue and X 30
represents a hydrocarbon substituent containing
No feeding was shown after two weeks incuba
tion of the mohair samples orlginallyimpreg . at least 4 carbon atoms and selected from the
nated with 3 and 5 per cent a-tertiary-butyl group consisting of the alkyl and cycloalkyl
phenoxy ethanol solutions.
radicals.
2. A process for mothproo?ng woolen fabrics
Example 3
,
and other materials subject to attack by moths
Dried samples of the impregnated woolen mo
which comprises treating such material with 4
hair were thoroughly washed in a 0.5 per cent so- ,
lution of Ivory soap in water at a temperature of
40° C. After 20 minutes contact with'the soap
40 solution, these test samples were rinsed in run
ning water, and dried. It was found that upon
infestation with the carpet beetle and two weeks
incubation the samples originally impregnated
with 5 per cent of i-tertiary-butyi phenoxy
45 ethanol were substantially free from injury.
In the foregoing examples no staining of the
impregnated cloth was observed and the fabric
itself was not damaged by the aryloxy alkylol
compound. The impregnated cloth in each in
stance was odorless, and even after prolonged
weathering showed no discoloration. The pre
servative showed no tendency to crystallize out
or to volatilize, from the fabric nor was the fabric
greasy or oily to the touch.
55
Among other aryloxy alnlol compounds which
may be similarly employed for the protection of
fabrics and the like against attack by moths are:
2-tertiary-butyl phenoxy ethanol, 3-tertiary
amyl phenoxy ethanol, 4-normal-butyl phenoxy
ethanol, 3-secondary-amyl phenoxy ethanol, 4
secondary-butyl phenoxy propanol,~ il-normal-amyl
phenoxy propanol, 2-normal-hen1 phenoxy pro
panol, i-tertiary-butyl phenoxy butanol, 2-cyclo
hexyl phenoxy ethanol, i-cyclohexyl phenoxy
ethanol, 2-cyclopentyl phenoxy ethanol, 3-cyclo
hexyl phenoxy propanol, i-cyclohex'yl phenoxy
propanol, 2-cyclohexyl phenoxy butanol, etc. .
tertiary-butyl phenom’ ethanol.
3. A process for mothproo?ng woolen fabrics
and other materials subject to attack by moths 40
which comprises treating such materials with a
composition comprising a-tertiary-butyl phenoxy
ethanol dissolved in an organic solvent.
4. A process for mothproo?ng woolen fabrics
and other materials subject to attack by moths 45
which comprises treating such materials with a
composition comprising i-tertiary-butyl phenom
ethanol dissolved in a light petroleum distillate.
5. A composition consisting of material liable
to attack by moths having incorporated therein
an aryloxy alkylol compound having the formula
wherein R represents an alLvl residue and X rep
resents a hydrocarbon substltuent containing at
least 4 carbon atoms and selected from the group
consisting of the alkyl and cylcloalkyl radicals.
6. A composition consisting of material liable
to attack by moths having incorporated therein
4-tertiary-butyl phenoxy ethanol.
‘
'
WILLIAM W. ALLEN.
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