Malodor counteractant compositions and methods for preparing...

Cleaning compositions for solid surfaces – auxiliary compositions – With oxygen – halogen – sulfur – or nitrogen containing or... – Ring in the component

Reexamination Certificate

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C512S023000

Reexamination Certificate

active

06432891

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention pertains to a method of counteracting a malodor in a solid or liquid, soap or detergent caused by a compound selected from the group consisting of lower carboxylic acids, thiols, thiophenols, phenols, lower amines, phosphines, arsines, lower alcohols, and lower ketones. The method comprises introducing into the solid or liquid, soap or detergent an effective malodor counteracting amount of a malodor counteracting compound selected from the group consisting of 1-cyclohexyl-ethyl-butyrate, 1-cyclohexyl-ethyl-acetate, 1-cyclohexyl-ethanol, 4-isopropyl-cyclohexyl-propionate, and phenoxyacetic acid 2-hydroxy-ethyl ester. The perceived total odor intensity in the solid or liquid, soap or detergent is reduced and the perceived malodor intensity in the solid or liquid, soap or detergent is substantially eliminated. The malodor counteractant compositions may be used in a wide variety of solid or liquid, soaps or detergents.
2. Description of the Background
A wide variety of solid and liquid, soaps and detergents have been developed for cleaning purposes that are offensive to the sense of smell. Particularly unpleasant odors are caused by compounds which have the ability to donate or accept protons such as lower carboxylic acids, thiols, thiophenols, phenols, lower amines, phosphines, arsines, lower alcohols, and lower ketones. Compounds of this type that have unpleasant odors are known as malodor compounds.
Conventional perfumes include a variety of fragrance materials that provide a pleasant perfume that masks the malodor compound generally by one of two mechanisms. In the first mechanism, the masking fragrance blends with the malodor compound to provide a different and more desirable aroma. In the second mechanism, the masking fragrance is employed in a large quantity to overwhelm the malodor compound.
Unfortunately both types of perfuming mechanisms have serious disadvantages. Neither perfume completely eliminates the perception of malodor and so there is a tendency to use increasing amounts of the fragrance to completely eliminate the perception of malodor. Furthermore, the masking effect is an additive effect and so the total odor level in the freshened solid or liquid, soap or detergent is increased by consumption of the perfume. Even though the fragrances used in the perfume may be very pleasant at low concentration, the total odor level in the solid or liquid, soap or detergent at the relatively high concentrations required to achieve moderate masking of the malodor may itself be offensive.
U.S. Pat. No. 4,009,253 (Schleppnik et al. '253) discloses a method of treating malodors to alleviate their offensiveness. The method comprises treating the air containing the malodor with an amount of 4-cyclohexyl-4-methyl-2-pentanone, CH
3
C(CH
3
)(C
6
H
11
)CH
2
COCH
3
, effective to counteract the malodor.
U.S. Pat. No. 4,187,251 (Schleppnik et al. '251) discloses the use of 4-ethylcyclohexyl methyl ketone, 4-CH
3
CH
2
(C
6
H
10
)COCH
3
, and 4-isopropylcyclohexyl methyl ketone, 4-(CH
3
)
2
CH(C
6
H
10
)COCH
3
. Other compounds disclosed as being useful in the invention are 4-tert-butylcyclohexyl methyl ketone, 4-(CH
3
)
3
C(C
6
H
10
)COCH
3
; 2-methyl-4-tert-butylcyclohexyl methyl ketone, 2-(CH
3
)-4-(CH
3
)
3
C(C
6
H
9
)COCH
3
; 2-methyl-5-isopropylcyclohexyl methyl ketone, 2-(CH
3
)-5-(CH
3
)
2
CH(C
6
H
9
)COCH
3
; 4-methylcyclohexyl isopropyl ketone, 4-(CH
3
)(C
6
H
10
)COCH(CH
3
)
2
; 4-methylcyclohexyl sec-butyl ketone, 4-(CH
3
)(C
6
H
10
)COCH(CH
3
)CH
2
CH
3
; 4-methylcyclohexyl isobutyl ketone, 4-(CH
3
)(C
6
H
10
)COCH
2
CH(CH
3
)
2
; 2,4-dimethylcyclohexyl methyl ketone, 2,4-(CH
3
)
2
(C
6
H
9
)COCH
3
; 2,3-dimethylcyclohexyl methyl ketone, 2,3-(CH
3
)
2
(C
6
H
9
)COCH
3
; 2,2-dimethylcyclohexyl methyl ketone, 2,2-(CH
3
)
2
(C
6
H
9
)COCH
3
; 3,3-dimethylcyclohexyl methyl ketone, 3,3-(CH
3
)
2
(C
6
H
9
)COCH
3
; 4,4-dimethylcyclohexyl methyl ketone, 4,4-(CH
3
)
2
(C
6
H
9
)COCH
3
; 3,3,5-trimethylcyclohexyl methyl ketone, 3,3,5-(CH
3
)
3
(C
6
H
8
)COCH
3
; and 2,2,6-trimethylcyclohexyl methyl ketone, 2,2,6-(CH
3
)
3
(C
6
H
8
)COCH
3
.
U.S. Pat. No. 4,310,512 (Schleppnik et al. '512) discloses a fragrance composition having malodor counteractant properties comprising a compound having malodor counteractant properties and fragrance materials. The compound having malodor counteractant properties has the formula: ABC—C
6
H
2
—X—(CH
2
)
n
COZ; wherein A, B and C are hydrogen or an alkyl group of 1 to 6 carbon atoms provided that the total combined number of carbon atoms of A, B, C does not exceed 8 carbon atoms; X is oxygen; n represents 1 to 2; and Z represents a monohydroxy alkyl group of 2 to 7 carbon atoms. Representative compounds include 2-hydroxyethyl phenoxyacetate, 2-hydroxyethyl p-tert-butylphenoxyacetate, 6-hydroxylhexyl phenoxyacetate, 4-hydroxybutyl phenoxyacetate, 3-hydroxypropyl-2′-methylphenoxyacetate, 3-hydroxy-1-butyl phenoxyacetate, 1-hydroxy-3-butyl phenoxyacetate, 3-hydroxypropyl phenoxyacetate, 2-hydroxy-1-propyl phenoxyacetate, 1-hydroxy-2-propyl phenoxyacetate, 2-hydroxy-1-propyl-p-isopropylphenoxyacetate, 1-hydroxy-2-propyl-p-isopropylphenoxyacetate, 2-hydroxyethyl 3′,4′-dimethylphenoxyacetate, 2′-hydroxyethyl 3-phenoxypropionate. The formula, ABC—C
6
H
2
—X—(CH
2
)
n
COZ, could include phenoxyacetic acid 2-hydroxy-ethyl ester (C
6
H
5
)OCH
2
COO(CH
2
)
2
OH.
U.S. Pat. No. 4,622,221 (Schleppnik et al. '221) discloses a method of counteracting a malodor in air caused by a compound selected from the group consisting of lower carboxylic acids, thiols, thiophenols phenols, lower amines, phosphines and arsines. The method comprises introducing into the air an effective malodor counteracting amount of cyclohexyl-1-ethyl-n-butyrate or cyclohexyl-1-ethyl-acetate whereby the perceived total odor intensity in the air is reduced and the perceived malodor intensity in the air is substantially eliminated.
Malodor counteractants having the formula C
6
H
11
—CR
1
R
2
OX are also disclosed. In this formula, R
1
is C
1-5
alkyl, R
2
is selected from the group consisting of hydrogen and C
1-5
alkyl and X is —COR
3
wherein R
3
is selected from the group consisting of hydrogen and C
1-6
alkyl. Schleppnik et al. '221 claims cyclohexyl-1ethyl-n-butyrate or cyclohexyl-1-ethyl-acetate.
U.S. Pat. No. 4,701,278 (Fehr) discloses a method to enhance flowery type perfume notes reminiscent of those developed by lily of the valley and coriander. The method comprises adding a fragrance effective amount of cyclohexyl-2-methyl-2-butanol, C
6
H
11
-(CH
2
)
2
C(CH
3
)
2
OH, in admixture with other perfume coingredients.
U.S. Pat. No. 4,719,105 (Schleppnik et al. '105) discloses a method of counteracting a malodor in air caused by a compound selected from the group consisting of lower carboxylic acids, thiols, thiophenols, phenols, lower amines, phosphines, and arsines. The method comprises introducing into the air an effective malodor counteracting amount of cyclohexyl-1-ethanol whereby the perceived total odor intensity in the air is reduced and the perceived malodor intensity in the air is substantially eliminated. Malodor counteractants having the formula C
6
H
11
—CR
1
R
2
OX are also disclosed. In this formula, R
1
is C
1-5
alkyl, R
2
is selected from the group consisting of hydrogen and C
1-5
alkyl and X is hydrogen. Schleppnik et al. '105 claims cyclohexyl-1-ethanol.
U.S. Pat. No. 5,049,544 (Koshino et al.) discloses a perfumery composition comprising 2-cyclohexylpropionic acid or a derivative represented by the formula: C
6
H
11
CH(CH
3
)COOR. In this formula, R is a hydrogen atom, an alkyl group having 1-4 carbon atoms, or an alkenyl group having 2-4 carbon atoms. Representative compounds include ethyl 2-cyclohexylpropionate, methyl 2-cyclohexylpropionate, 2-cyclohexylpropionic acid, isopropyl 2-cyclohexylpropionate, 2-cyclohexylpropionate, and tert-butyl 2-cyclohexylpropionate.
U.S. Pat. No. 5,100,872 (Narula et al.) discloses a number of alkyl cy

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