U.S. patent application number 14/814823 was filed with the patent office on 2015-11-26 for low volatile reactive malodor counteractives and methods of use thereof.
This patent application is currently assigned to INTERNATIONAL FLAVORS & FRAGRANCES INC.. The applicant listed for this patent is Xiao HUANG, Johan Gerwin Lodewijk PLUYTER, Takashi SASAKI. Invention is credited to Xiao HUANG, Johan Gerwin Lodewijk PLUYTER, Takashi SASAKI.
Application Number | 20150336877 14/814823 |
Document ID | / |
Family ID | 47046437 |
Filed Date | 2015-11-26 |
United States Patent
Application |
20150336877 |
Kind Code |
A1 |
PLUYTER; Johan Gerwin Lodewijk ;
et al. |
November 26, 2015 |
LOW VOLATILE REACTIVE MALODOR COUNTERACTIVES AND METHODS OF USE
THEREOF
Abstract
The present invention provides a novel compound for
counteracting amine-based malodor in consumer, industrial and
textile products.
Inventors: |
PLUYTER; Johan Gerwin Lodewijk;
(Middletown, NJ) ; SASAKI; Takashi; (Matawan,
NJ) ; HUANG; Xiao; (Freehold, NJ) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
PLUYTER; Johan Gerwin Lodewijk
SASAKI; Takashi
HUANG; Xiao |
Middletown
Matawan
Freehold |
NJ
NJ
NJ |
US
US
US |
|
|
Assignee: |
INTERNATIONAL FLAVORS &
FRAGRANCES INC.
New York
NY
|
Family ID: |
47046437 |
Appl. No.: |
14/814823 |
Filed: |
July 31, 2015 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
|
|
13277288 |
Oct 20, 2011 |
9126890 |
|
|
14814823 |
|
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|
Current U.S.
Class: |
424/76.1 ;
536/123.1; 560/174 |
Current CPC
Class: |
A61L 9/01 20130101; C07C
205/44 20130101; C08B 30/00 20130101; C07B 2200/11 20130101; C07C
323/22 20130101; C07C 223/06 20130101; C07C 69/675 20130101; C07C
229/08 20130101 |
International
Class: |
C07C 229/08 20060101
C07C229/08; C07C 69/675 20060101 C07C069/675; A61L 9/01 20060101
A61L009/01; C08B 30/00 20060101 C08B030/00 |
Claims
1. A consumer, industrial or textile product comprising a malodor
counteractant compound comprising a .alpha.-keto moiety covalently
attached to (a) polymer comprising an olefin, polysaccharide,
polyamine, polyacrylate, polyalkylene oxide with OH or NH.sub.2 end
groups, or block or random copolymer thereof; (b) an oligomer
comprising an oligosaccharide or oligomeric alkane; (c) a
surfactant comprising diblock or triblock copolymers of ethylene
oxide, propylene oxide or butylene oxide, or poloxamine; or (d) a
solid surface comprising a silica or clay surface, wherein the
.alpha.-keto moiety comprises a ketone which is capable of reacting
with malodors.
2. The consumer, industrial or textile product of claim 1, wherein
the .alpha.-keto moiety comprises levulinic acid, acetoacetic acid,
pyruvic acid, .alpha.-ketoglutaric acid, .alpha.-ketobutyric acid,
.alpha.-ketoisocaproic acid, or .alpha.-ketovaleric acid.
3. The consumer, industrial or textile product of claim 1, wherein
the malodor counteractant compound has the structure: ##STR00007##
wherein X represents O, N, or C; wherein n represents an integer of
0 or greater; and wherein R is (a) polymer comprising an olefin,
polysaccharide, polyamine, polyacrylate, polyalkylene oxide with OH
or NH.sub.2 end groups, or block or random copolymer thereof; (b)
an oligomer comprising an oligosaccharide or oligomeric alkane; (c)
a surfactant comprising diblock or triblock copolymers of ethylene
oxide, propylene oxide or butylene oxide, or poloxamine; or (d) a
solid surface comprising a silica or clay surface.
4. The consumer, industrial or textile product of claim 3, wherein
X is NH, n is an integer of 0 to 2, and R is a copolymer of
ethylene oxide and propylene oxide.
5. A method for producing a malodor counteractant compound
comprising covalently attaching a .alpha.-keto moiety to (a)
polymer comprising an olefin, polysaccharide, polyamine,
polyacrylate, polyalkylene oxide with OH or NH.sub.2 end groups, or
block or random copolymer thereof; (b) an oligomer comprising an
oligosaccharide or oligomeric alkane; (c) a surfactant; or (d) a
solid surface comprising a silica or clay surface.
6. A malodor counteractant compound comprising an .alpha.-keto
moiety covalently attached to: (a) a polymer comprising an olefin,
polysaccharide, polyamine, polyacrylate, polyalkylene oxide with OH
or NH.sub.2 end groups, or block or random copolymer thereof; (b)
an oligomer comprising an oligosaccharide or oligomeric alkane; (c)
a surfactant comprising diblock or triblock copolymers of ethylene
oxide, propylene oxide or butylene oxide, or poloxamine; or (d) a
solid surface comprising a silica or clay surface, wherein the
.alpha.-keto moiety comprises a ketone which is capable of reacting
with malodors.
7. The malodor counteractant compound of claim 6, wherein the
.alpha.-keto moiety comprises levulinic acid, acetoacetic acid,
pyruvic acid, .alpha.-ketoglutaric acid, .alpha.-ketobutyric acid,
.alpha.-ketoisocaproic acid, or .alpha.-ketovaleric acid.
8. The malodor counteractant compound of claim 6, wherein the
malodor counteractant compound has the structure: ##STR00008##
wherein X represents O, N, or C; wherein n represents an integer of
0 or greater; and wherein R is a (a) polymer comprising an olefin,
polysaccharide, polyamine, polyacrylate, polyalkylene oxide with OH
or NH.sub.2 end groups, or block or random copolymer thereof; (b)
an oligomer comprising an oligosaccharide or oligomeric alkane; (c)
a surfactant comprising diblock or triblock copolymers of ethylene
oxide, propylene oxide or butylene oxide, or poloxamine; or (d) a
solid surface comprising a silica or clay surface.
9. The malodor counteractant compound of claim 8, wherein X is NH,
n is an integer of 0 to 2, and R is a copolymer of ethylene oxide
and propylene oxide.
10. A method for counteracting an amine-based malodor of a
consumer, industrial or textile product or the surrounding
environment thereof comprising the step of adding the malodor
counteractant compound of claim 6 to the product and reducing the
presence of an amine-based malodor of the consumer, industrial or
textile product.
Description
CROSS-REFERENCE TO RELATED APPLICATIONS
[0001] This application claims priority to U.S. patent application
Ser. No. 13/277,288 filed on Oct. 20, 2011, the content of which is
incorporated herein by reference in its entirety.
BACKGROUND OF THE INVENTION
[0002] Malodors are offensive odors, which are encountered in the
air and on many substrates such as fabrics, hard surfaces, skin,
and hair. Amines, thiols, sulfides, short chain aliphatic and
olefinic acids, e.g. fatty acids, are typical of the chemicals
found in and contributed to sweat, household, and environmental
malodors. These types of malodors typically include indole,
skatole, and methanethiol found in toilet and animal odors;
piperidine and morpholine found in urine; pyridine and triethyl
amine found in kitchen and garbage odors; and short chain fatty
acids, such as 3-methyl-3-hydroxyhexanoic acid, 3-methylhexanoic
acid or 3-methyl-2-hexenoic acid, found in axilla malodors.
Compounds which have been found in the axilla are described for
example by Xiao-Nong Zeng, et al. (1991) J. Chem. Ecol.
17:1469-1492.
[0003] Malodor counteractants or masking agents have been described
in the art. For example, sulthydryl reactants, such as diethyl
fumarate, di-n-butyl maleate and N-ethylmaleimide are disclosed in
U.S. Pat. No. 5,601,809 as compounds that are effective against
axillary malodor. Further, the use of certain aromatic unsaturated
carboxylic acid esters in combination with alkyl fumarates as
malodor counteractants is disclosed in U.S. Pat. No. 6,610,648.
U.S. Pat. No. 6,403,075 addresses fragrance materials with a phenyl
ring moiety as ammonia masking agents. Similarly, US 2002/0058017
describes cis-3-hexenol to mask ammonia. Moreover, U.S. Pat. No.
7,585,833 describes methods for formulating fragrances to mask
malodor present in products containing ammonia and substituted
amines (See, U.S. Pat. No. 6,379,658, U.S. Pat. No. 6,376,741, U.S.
Pat. No. 5,769,832, and U.S. Pat. No. 5,037,412).
[0004] Although the art describes compositions and methods for
neutralizing certain malodors, there still remains a need for
additional compounds that are more efficient against malodors.
SUMMARY OF THE INVENTION
[0005] The present invention features a malodor counteractant
compound composed of a .alpha.-keto moiety covalently attached to a
polymer, an oligomer, a surfactant, or a solid surface. In one
embodiment, the .alpha.-keto moiety of the malodor counteractant
compound is, for example, but not limited to, levulinic acid,
acetoacetic acid, pyruvic acid, .alpha.-ketoglutaric acid,
.alpha.-ketobutyric acid, .alpha.-ketoisocaproic acid, or
.alpha.-ketovaleric acid. In other embodiments, the polymer is, for
example, but not limited to, a polyol, polysaccharide, polyamine,
polyacrylate, alkene oxide polymer, or block or random copolymer
thereof; the oligomer is, for example, but not limited to, an
oligosaccharide or oligomeric alkane; the surfactant is, for
example, but not limited to, a poloxamine or an unbranched
C.sub.13-C.sub.15 oxo alcohol; and the solid surface is, for
example, but not limited to, a silica or clay surface. In still
other embodiments, the malodor counteractant compound has the
structure:
##STR00001##
[0006] wherein X represents O, N, or C;
[0007] wherein n represents an integer of 0 or greater; and
[0008] wherein R is a polymer, an oligomer, a surfactant, or a
solid surface, and wherein the polymer is (a) polyalkylene oxide
with OH or NH.sub.2 end groups such as polyethyleneoxide,
polypropyleneoxide, polytetrahydrofuran, polyetheramine, a block or
random copolymer variant thereof such as Pluronics.RTM. or
Synperonics.RTM., or a branched copolymer such as a tetronic
polymer; (b) polyvinyl amine or a copolymer with vinyl formamide or
vinyl acetamide; (c) polyvinyl alcohol or a copolymer with vinyl
acetate, olefin such as ethylene and propylene, or acrylate; or (d)
biopolymer such as polysaccharide (i.e., maltodextrin, starch,
guar, xanthan, carboxymethyl cellulose, hydroxyethyl cellulose,
carrageenan, or cationic/amphoteric/hydrophobically substituted
polysaccharide).
[0009] Consumer, industrial and textile products containing the
above malodor counteractant are also provided as are methods for
producing the above malodor counteractant and using the above
malodor counteractant to counteract amine-based malodor.
DETAILED DESCRIPTION OF THE INVENTION
[0010] The present invention provides compounds composed of an
.alpha.-keto moiety covalently attached to a polymer, an oligomer,
a surfactant (nonionic with OH, NH.sub.2 or COOH groups), or a
solid surface (silica or clay) for use as malodor counteractants.
Advantageously, the .alpha.-keto moiety of the malodor
counteractant compounds of the present invention binds to
amine-based malodors thereby effectively reducing the concentration
of these malodors in consumer, industrial or textile products.
Moreover, the compounds of the present invention have a low vapor
pressure such that the compounds can be added in significant
quantities to products without impacting the olfactory character of
the products. Given these features, the compounds of the present
invention find use as additives to consumer products to reduce the
concentration of malodors in the headspace of the product.
Furthermore, the compounds of the present invention can be used to
form a fragrance or flavor encapsulate or other delivery system
such that while the delivery system is delivering its payload,
malodors are removed from the air. Alternatively, the compounds of
the present invention can be formulated into a product, such as a
fragrance, which can be optionally formulated into a delivery
system.
[0011] As indicated, particular embodiments feature compounds with
low-to-no vapor pressure. Vapor pressure)(P.degree.) is the
pressure of a vapor of a compound in equilibrium with its pure
condensed phase (solid or liquid). Vapor pressure is measured in
the standard units of pressure. The International System of Units
(SI) recognizes pressure as a derived unit with the dimension of
force per area and designates the pascal (Pa) as its standard unit.
One pascal is one Newton per square meter (Nm.sup.-2 or
kgm.sup.-1s.sup.-2). Vapor pressures depend on the temperature and
vary with different compounds due to differences in
molecule-molecule interactions. For example, vapor pressure at
25.degree. C. of n-alkanes is a function of chain length, wherein
larger n-alkane molecules have lower P.degree. due to greater
polarizability and increased strength of London Dispersion
intermolecular forces. The vapor pressure of a compound can be
determined by conventional methods known to those of skill in the
art. In particular embodiments, compounds of the present invention
have a vapor pressure of less than 200 Pa (1.5 mmHg), less than 100
Pa (0.75 mmHg), less than 50 Pa (0.375 mmHg), less than 20 Pa (0.15
mmHg), or less than 10 Pa (0.075 mmHg), at 25.degree. C.
[0012] The .alpha.-keto moiety of the malodor counteractant
compound of the present invention is, in particular embodiments,
levulinic acid, acetoacetic acid, pyruvic acid,
.alpha.-ketoglutaric acid, .alpha.-ketobutyric acid,
.alpha.-ketoisocaproic acid, or .alpha.-ketovaleric acid. The
.alpha.-keto moiety is covalently attached to a polymer, an
oligomer, a surfactant, or a solid surface. Accordingly, in certain
embodiments, the malodor counteractant compound of the present
invention has the structure:
##STR00002##
[0013] wherein X represents O, N, or C;
[0014] wherein n represents an integer of 0 or greater; and
[0015] wherein R is a polymer, an oligomer, a surfactant, or a
solid surface.
[0016] A polymer in accordance with the present invention is a
molecule composed of repeating monomer units. In contrast to a
polymer, which can contain numerous monomers, an oligomer is a
molecule that is composed of a few monomer units. In this respect,
oligomers include dimers, trimers, tetramers, and the like.
According to the present invention, a polymer includes, but is not
limited to, a polyol (e.g., polyvinyl alcohol or a copolymer with
vinyl acetate, olefin such as ethylene and propylene, or acrylate);
biopolymer such as polysaccharide (e.g., maltodextrin, starch,
guar, xanthan, carboxymethyl cellulose, hydroxyethyl cellulose,
carrageenan, or cationic/amphoteric/hydrophobically substituted
polysaccharide); polyamine (e.g., polyvinyl amine or a copolymer
with vinyl formamide or vinyl acetamide); polyacrylate with alcohol
groups; and polyalkylene oxide with OH or NH.sub.2 end groups
(e.g., polyetheramine). The polyalkylene oxide of the present
invention is an alkyl ether having from 4 to 25, preferably 4-16,
moles of ethylene oxide per mole of alkyl phenol (e.g.,
polyethylene glycol (PEG), polyethylene oxide (PEO),
polypropyleneoxide, and polytetrahydrofuran) and a block or random
copolymer variant thereof or a branched copolymer such as a
tetronic polymer. An oligomer includes, but not limited to, e.g.,
oligosaccharides and oligomeric alkanes (e.g., pentanes, butanes,
or hexane). A surfactant of the present invention is a compound
that lowers the surface tension of a liquid or the interfacial
tension between two liquids or between a liquid and a solid. A
surfactant may act as a detergent, wetting agent, emulsifier,
foaming agent, or dispersant. A surfactant is usually an organic
compound that is amphiphilic. Surfactants include molecules such as
PLURONIC.RTM. surfactants (based on ethylene oxide, propylene oxide
and/or butylenes oxide as di- and tri-block copolymers) and
TETRONIC.RTM. surfactants (poloxamine or block copolymers based on
ethylene oxide and propylene oxide with a vapor pressure of <0.1
mmHg at 25.degree. C.) including TETRONIC.RTM. 901, TETRONIC.RTM.
701, TETRONIC.RTM. 90R4, and TETRONIC.RTM. 904, and LUTENSOL.RTM.
AO nonionic surfactants (unbranched C.sub.13-C.sub.15 oxo alcohol)
including LUTENSOL.RTM. AO3, LUTENSOL.RTM. AO4, LUTENSOL.RTM. AO5,
and LUTENSOL.RTM. AO7.
[0017] A solid surface of the present invention includes, but is
not limited to a silica surface (e.g., a synthetic amorphous silica
surface such as SYLOID.RTM.), clay or other solid mineral materials
with an appropriate functional group to attach the .alpha.-keto
moiety. In another embodiment, the solid surface is the surface of
a delivery system such as a nanoparticle, microparticle,
nanocapsule or microcapsule, which attaches to one or more
.alpha.-keto moieties.
[0018] In particular embodiments, the malodor counteractant
compound of the present invention is a small molecule with
no-to-low vapor pressure attached to one or more .alpha.-keto
groups. In another embodiment, the malodor counteractant compound
of the present invention is a polymer attached to one or more
.alpha.-keto groups. In a further embodiment, the malodor
counteractant compound of the present invention is an oligomer with
one or more .alpha.-keto groups attached thereto. In another
further embodiment, the malodor counteractant compound of the
present invention is a surfactant attached to one or more
.alpha.-keto groups. In still a further embodiment, the malodor
counteractant compound of the present invention is a solid surface
attached to one or more .alpha.-keto groups.
[0019] Specific examples of malodor counteractant compounds of the
present invention include, but are not limited to, the following
examples:
##STR00003##
[0020] Malodor counteractant compounds of the present invention are
produced by covalently attaching a .alpha.-keto moiety as described
herein to a polymer, an oligomer, a surfactant, or a solid surface.
Given that the .alpha.-keto moiety is covalently attached, this
moiety is not released before or during use in a consumer,
industrial or textile product, e.g., the compounds of the present
invention are not pro-fragrances. Specific examples of reagents and
reactions conditions for preparing the compounds of the present
invention are provided in Examples.
[0021] The malodor counteractant compounds of the present invention
can be used in a variety of forms and in a variety of products.
Advantageously, the compounds of the present invention are reactive
against potent malodor ingredients while not affecting the odor of
a fragrance or final product. Furthermore, these compounds and the
methods herein can be pursued in any situation where malodor is
present. In this respect, the present invention also features a
method for counteracting amine-based malodor of consumer,
industrial and textile products, as well as the surrounding
environment, by introducing or adding one or more malodor
counteractant compounds of the present invention to a consumer,
industrial or textile product so that the amine-based malodor of
the product is counteracted.
[0022] The .alpha.-keto containing malodor counteractant compounds
of the present invention may react with amine-based malodor
molecules, for example, but not limited to, according to the
following schemes:
##STR00004##
[0023] wherein X, n, and R are defined the same as above: and
Y--NH.sub.2 represents an amine-based malodor molecule;
##STR00005##
[0024] wherein X, n, R, and Y--NH.sub.2 are defined the same as
above.
[0025] For the purposes of the present invention, a compound
counteracts a malodor if it measurably (either qualitatively or
quantitatively) reduces the presence of a malodor. In particular
embodiments, the malodor counteractant compounds of the present
invention reduce the presence of amine-based malodor of a product
by 50-100% as compared to a product that does not have the malodor
counteractant compounds.
[0026] Malodors particularly targeted by the compounds of the
present invention include amine-based malodor such as bathroom
odors, sweat, food odors, textile odors, home care and personal
care product base odors, adhesive odors, and paint odors. In this
respect, the compounds of the present invention can be used in air
refresheners, fabric refresheners, bar soaps, perfumes, fragrances,
cologne, bath or shower gels, shampoos or other hair care products,
cosmetic preparations, body odorants, deodorants, antiperspirants,
liquid or solid fabric detergents or softeners, bleach products,
disinfectants or all-purpose household or industrial cleaners,
food, or industrial or textile products such as adhesives, paints,
coatings, or textiles. In yet another embodiment, one or more of
the compounds of the present invention are used as part of a
delivery system or polymer system to deliver a fragrance or
compound of interest (e.g., a pharmaceutical).
[0027] The following are provided as specific embodiments of the
present invention. Other modifications of this invention will be
readily apparent to those skilled in the art. Such modifications
are understood to be within the scope of this invention. All
reagents were purchased from Sigma-Aldrich, Inc. unless otherwise
noted. Further, as used herein all percentages are weight percent
unless otherwise noted, ppm is understood to be parts per million,
L is understood to be liter, mL is understood to be milliliter,
.mu.L is understood to be microliter, mol is understood be mole,
mmol is understood be millimole, and M is understood to be moles
per L. IFF as used in the examples is understood to mean
International Flavors & Fragrances Inc., New York, N.Y.,
USA.
Example I
##STR00006##
[0028] Preparation of Levulinic Acid Chloride
[0029] Oxalyl chloride in dichloromethane (2 M, 450 mL, 0.9 mol)
was added drop-wise to a stirring mixture of levulinc acid (100 g,
0.857 mol) and dimethylformamide (DMF, 2 mL) for about 1.5 to 2
hours at room temperature. After the addition was completed, the
resulting mixture was stirred for additional 0.5 hours. Solvents
were removed in vacuo and the crude mixture was used in subsequent
reactions.
Example II
Preparation of Levulinic Tetronics (Formula III)
[0030] Triethylamine (6.91 mL, 49.50 mmol) was added to a stirring
mixture of Tetronic.RTM. 901 (23.5 g, 24.77 mmol) dissolved in
dichloromethane (150 mL) under nitrogen atmosphere at 0-5.degree.
C. Levulinic acid chloride (prepared as above in EXAMPLE I) was
then added drop-wise. The resulting mixture was warmed to room
temperature and stirred for overnight. Triethylammonium chloride
salt was subsequently filtered off. The organic layer was washed
with saturated Na.sub.2CO.sub.3 and concentrated in vacuo to afford
the product levulinate tetronic with greater than 90%
functionalization determined by NMR spectroscopy.
Example III
Preparation of Levulinate Maltrin QD.RTM. M585 Maltodextrin
[0031] Triethylamine (12.5 g, 0.124 mmol) was added to a stirring
mixture of Maltrin QD.RTM. M585 maltodextrin (16.2 g, 0.100 mol)
dissolved in DMF (60 mL) under nitrogen atmosphere at 0-5.degree.
C. The mole ratios of maltodextrin herein were based on monomer
molecular structure of the entire polymeric chain. Levulinic acid
chloride (prepared as above in EXAMPLE I) was then added drop-wise.
The resulting mixture was warmed to room temperature and stirred
for overnight. The triethylammonium chloride salt was subsequently
filtered off Precipitate was collected with a mixture of
tetrahydrofuran (THF)/isopropanol (IPA) at a volume ratio of 1:9
(THF:IPA). The solid was filtered, washed several times with the
THF:IPA mixture, and dried under vacuum to afford the product
levulinate Maltrin QD.RTM. M585 maltodextrin with about 15-20%
functionalization determined by NMR spectroscopy.
Example IV
Preparation of Levulinate Lutensol.RTM. AO 7
[0032] Triethylamine (11.7 g, 0.115 mol) was added to a stirring
mixture of Lutensol.RTM. AO 7 (20.0 g, 57.5 mmol) dissolved in
acetone (150 mL) under nitrogen atmosphere at 0-5.degree. C.
Levulinic acid chloride (prepared as above in EXAMPLE I) was then
added drop-wise. The resulting mixture was warm toed room
temperature and stirred for overnight. The triethylammonium
chloride salt was filtered off. The solvent was concentrated in
vacuo to afford the product levulinate Lutensol.RTM. AO7 with
greater than 85% functionalization determined by NMR
spectroscopy.
Example V
Preparation of Octyl Levulinate (Formula VII)
[0033] 1-Bromooctane (332 g, 1.72 mol) was added to a stirring
mixture of levulinic acid (200 g, 1.72 mol), tetrabutylammonium
bromide (55.1 g, 0.17 mol), and K.sub.2CO.sub.3 (357 g, 2.58 mol)
in DMF (500 mL) drop-wise and stirred at room temperature for
overnight. The resulting mixture was diluted in toluene and the
organic layer was washed with HCl (10%), brine, and water. The
solvent was concentrated in vacuo and the oil was purified by
vacuum distillation to afford the product octyl levulinate as a
clear oil.
Example VI
Preparation of 4-Octyloxy Benzaldehyde
[0034] A mixture of 4-hydroxybenzaldehyde (10.0 g, 81.8 mmol),
1-bromooctane (15.8 g, 81.8 mmol), and K.sub.2CO.sub.3 (34.0 g,
0.25 mol) in DMF (150 mL) was heated to reflux for 8 hours and then
cooled to room temperature. The reaction mixture was subsequently
diluted in toluene. The organic layer was washed with HCl (10%),
brine, and water. The solvent was concentrated in vacuo and the oil
was purified by short silica gel plug (dichloromethane (DCM) in
n-hexanes, 10%). Solvent was dried in vacuo to afford the product
4-octyloxy benzaldehyde as a slightly colored oil.
Example VII
Testing Procedure
[0035] The testing procedure described herein was applicable to
malodor counteractant compounds containing water-soluble, modified
polymers, oligomers, or surfactants.
[0036] A solution of n-butyl amine (nBA) in methanol (0.05% by
weight, 500 ppm) was prepared and stored at 0.degree. C. in a
refrigerator prior to use. A solution of a malodor counteractant
compound to be tested was prepared (50 to 100 mL) with distilled
(DI) water and thoroughly mixed with a magnetic stir bar. The nBA
solution was added to the solution of the malodor counteractant
compound and the molar ratio of the malodor counteractant compound
and nBA was adjusted to 1:1. For a polymer-containing malodor
counteractant compound, the averaged molecular weight of the
polymer was used for this calculation. Water or diethyl phthalate
(DEP) containing the same amount of nBA as the test group was used
as a control.
[0037] For analysis, the aqueous polymer/surfactant (1 mL) was
placed into a 20 mL headspace vial using a positive displacement
pipette. nBA solution (0.05%, 250 .mu.L) was subsequently added
into the vial. The vial was then capped immediately. The vial was
placed in a holder and set on an orbital incubator for a
pre-selected mixing/equilibration time. An aliquot of headspace
above the reaction solution was then sampled and injected into the
gas chromatograph for separation and detection.
[0038] Proof of Reactivity of nBA with .alpha.-Keto-Containing
Molecules:
[0039] The ability of .alpha.-keto-containing molecules to reduce
the amount of amine-based malodor was determined. Water was used as
the control. The results are presented in the following:
TABLE-US-00001 .alpha.-Keto-Containing Molecules Malodor Reduction
2-Pentanon 75% at 1 hour and 83% at 12 hours Ethyl levulinate 41%
at 1 hour and 69% at 12 hours Butyl levulinate 39% at 1 hour and
62% at 12 hours Octyl levulinate (Formula VII) 75% at 1 hour and
78% at 12 hours
Example VIII
Evaluation of Malodor Counteractant Compounds
[0040] The malodor counteracting effect of malodor counteractant
compounds containing a .alpha.-keto moiety covalently attached to a
polymer including PEG-dilevulinate, TETRONIC.RTM. 701
tetra-levulinate, and TETRONIC.RTM. 901 tetra-levulinate were
evaluated following the testing procedure described as above. The
mixing/equilibration time was an hour. DEP was used as the control.
The results are presented in the following:
TABLE-US-00002 Malodor Counteractant Compounds Malodor Reduction
PEG-dilevulinate 4% TETRONIC .RTM. 701 tetra-levulinate 97%
TETRONIC .RTM. 901 tetra-levulinate 75%
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