US008603963B1

(12) United States Patent (10) Patent N0.: US 8,603,963 B1

Steward et a1. (45) Date of Patent: Dec. 10, 2013

(54) FRAGRANCE COMPOSITIONS CONTAINING 6,617,483 B1 * 9/2003 McKim et al. .............. .. 585/833
LOW VAPOR PRESSURE VOC SOLVENTS 6,869,923 B1 3/2005 Cunningham et al.
7,481,380 B2 1/2009 Kvietok et al.
2003/0024997 A1* 2/2003 Welch et al. .................. .. 239/53
(75) Inventors: Charles C. Steward, Rockleigh, NJ 2004/0116325 A1* 6/2004 Goodacre et al. ...... . . . .. 512/10
(US); Lambert Dekker, Rockleigh, NJ 2004/0144406 A1* 7/2004 Garabedian et al. 134/26
(US); Henry van den Heuvel, 2005/0214386 A1* 9/2005 Shaheen et al. 424/661
Rockleigh, NJ (US) 2005/0217698 A1* 10/2005 Mitchell et al. .... . . . . . .. 134/6

2005/0250668 A1* 11/2005 Serobian et al. 510/466

2006/0276356 A1* 12/2006 Panandiker et al. ........ .. 510/100
(73) Assignee: Takasago International Corporation, 2007/0176015 A1 8/2007 Farrell et al.
Tokyo (JP) 2007/0191253 A1* 8/2007 Kilkenny et a1. ........... .. 510/424
2008/0193387 A1 8/2008 De Wolff et al.
Notice: Subject to any disclaimer, the term of this 2008/0308648 A1 12/2008 Pesu
patent is extended or adjusted under 35 2009/0022682 A1 1/2009 Licciardello et al.
2009/0117069 A1* 5/2009 MainZ ........................ .. 424/76.4
U.S.C. 154(b) by 48 days. 2009/0148342 A1 * 6/2009 Bromberg et al. ............ .. 422/37

(21) Appl. No.: 12/717,078 FOREIGN PATENT DOCUMENTS

(22) Filed: Mar. 3, 2010 CA 2662806 7/2009
CA 2662816 7/2009
Related US. Application Data
OTHER PUBLICATIONS
(60) Provisional application No. 61/157,181, ?led on Mar.
3, 2009. “A hydrophilic glycol either with a moderate evaporation rate and
tailing solvent activities”; DOWANOL DPMA, Mar. 2004; pp. 1-2.
(51) Int. Cl.
A61Q 13/00 (2006.01) * cited by examiner
A61L 9/03 (2006.01)
A61L 9/12 (2006.01)
(52) Us. or. Primary Examiner * Douglas McGinty
USPC ........ .. 512/2; 512/3; 512/25; 512/26; 239/34; (74) Attorney, Agent, or Firm * Baker Botts L.L.P.
239/44
(58) Field of Classi?cation Search
(57) ABSTRACT
USPC ..................... .. 512/1, 3, 2, 25, 26; 239/44, 34
See application ?le for complete search history. A fragrance composition comprising a loW vapor pressure
VOC and at least one loW vapor pressure VOC potentiator
(56) References Cited
compound, Which reduces, or altogether completely obviates
U.S. PATENT DOCUMENTS the use of HVPVOC solvents in fragrance compositions.

5,160,494 A 11/1992 Krzysik et al.

6,491,728 B2 12/2002 Bacon et a1. 17 Claims, 3 Drawing Sheets
US. Patent Dec. 10, 2013 Sheet 1 of3 US 8,603,963 B1

Figure 1

Evapora?on Comparison Between

COMP. MA, A’ m A, In Llquld Electrical Air Freshener

20
US. Patent Dec. 10, 2013 Sheet 2 of3 US 8,603,963 B1

Figure 2

Evaporation Comparison Between

Cami {51m 3' m B '1 in Liquid Eleclrical Air Freshener

Days
US. Patent Dec. 10, 2013 Sheet 3 of3 US 8,603,963 B1

Figgg 3

Evapornln m lor
Fem. a In lzlquild ihn?'lnil?ri'reshanlr
wanes 0P5 urns)

1 +1.01! Wk

2“$85.259 oBa.2
Fold! . C

20 30
 US 8,603,963 B1
1 2
FRAGRANCE COMPOSITIONS CONTAINING fragrance components that are economical to produce and
LOW VAPOR PRESSURE VOC SOLVENTS have good safety characteristics, including loW toxicity and
loW ?ammability.
CROSS REFERENCE TO RELATED Another and related object of the invention is to provide
APPLICATIONS fragrance compositions that include a loW pressure VOC
(e.g., DPMA) and a fragrance composition having a control
The present application claims the bene?t ofU.S. Ser. No. lable evaporation rate and that are suitable for use in, for
61/157,181, ?led Mar. 3, 2009, Which is hereby incorporated example, a Wick type air fragrance dispenser (air freshener).
herein by reference in its entirety. More speci?cally, it is an object of the invention to provide a
controllable evaporation rate and permit effective utiliZation
FIELD OF THE INVENTION of the fragrance in a liquid electrical air freshener dispenser.
The present invention relates to fragrance compositions SUMMARY OF THE INVENTION
containing loW vapor pressure VOC (volatile organic com
pound) solvents. The presently disclosed subject matter provides speci?
cally designed fragrance components that can be used in
BACKGROUND OF THE INVENTION
combination With loW vapor pressure VOCs (e.g., DPMA).
Surprisingly, it has been found that the use of one or more loW
A problem in the area of air care devices is the uncontrolled
vapor pressure VOCs, particularly DPMA, and specially con
“distillation” of fragrance components of differing volatili 20
structed fragrance components that include at least one loW
ties, resulting in a variable fragrance pro?le over time, as vapor pressure VOC potentiator compound can maintain the
perceived by the consumer. The use of carriers or solvents in volatility so that the composition performs properly in a elec
fragrances aids in the uniform distribution or evaporation of trical liquid air freshener device.
these fragrance components and leads to a more homoge One aspect of the presently disclosed subject matter pro
neous fragrance pro?le. 25
vides a fragrance composition that includes a loW vapor pres
Many materials are used as carriers in air care devices
sure VOC (e.g., dipropylene glycol methyl ether acetate) and
including glycol ethers, isopara?inic solvents (e.g., Isopar® at least one loW vapor pressure VOC potentiator compound.
solvents commercially available from ExxonMobil) and vari In one embodiment, the fragrance composition contains at
ous branched esters. One problem associated With these mate least 10 Wt %, or at least 15 Wt %, or at least 20 Wt %, or at least
rials is that many are classi?ed as VOCs (volatile organic 30
30 Wt % of VOC potentiator compounds, based on the total
compounds). VOC’s are increasingly of environmental and Weight of the fragrance composition. In an alternative
regulatory concern. There is one class of VOCs, loW vapor embodiment, the fragrance composition contains at least 10
pressure VOC’s (LVPVOCs), that are not as harmful to the Wt %, or at least 20 Wt % of the least one loW vapor pressure
atmosphere and are generally alloWed under even the most VOC, based on the total Weight of the fragrance composition.
stringent environmental regulations. This class of VOC has 35
In one embodiment, at least one loW vapor pressure VOC
loWer vapor pressure than regular VOCs as de?ned by stan potentiator compound present in the fragrance composition
dard de?nitions (e.g., <01 mm Hg at 20° C.). has a vapor pressure, at 25° C., ofat least about 0.2 mmHg, or
U.S. Published Application No. 2008/0308648 discloses, at least about 0.5 mmHg, or at least 1 mmHg, and/or a ?ash
in the generic sense, fragrance compositions containing DoW point from about 1 10° F. to about 200° F., or from about 130°
anol DPMA for use in a non-electric, Wick-type device. 40
F. to about 180° F.
DPMA has not, heretofor, been Widely used as a fragrance In one embodiment, one or more VOC potentiator com
carrier in liquid electrical air freshener devices, if used at all. pound(s) are represented by the formula:
The loW volatility of loW vapor pressure VOCs, such as
DPMA, presents unique challenges. The decreased vapor
pressure changes the compositions’ perceived fragrance pro 45
?le, as compared to the same fragrance composition used
With a high vapor pressure VOC solvent (HVPVOC solvent).
There is a need for hedonically pleasing fragrance compo
R \o iv.
sitions that can be combined With loW vapor pressure VOC
solvents, such as dipropylene glycol methyl ether acetate. For 50 Wherein
example, there is a need for fragrance compositions that can R is a Cl-Cl0 substituted or unsubstituted alkyl, alkenyl
be combined With a loW vapor pressure VOC carrier for use in group, or a C4-C8 substituted or unsubstituted cycloalkyl or
a liquid electrical air freshener, such as a heated Wick delivery aryl group; and
system, a pieZoelectrical spraying system, an electrospray X is hydrogen, or a C l-C5 unsubstituted alkyl group.
device or a Venturi device. It is desired to provide fragrance 55 In one embodiment, R is a C4-C8 substituted or unsubsti
compositions suitable for use in air fresheners that avoid the tuted alkyl group. In one embodiment, R is a C6 substituted or
regulatory problems associated With many of the glycol ether unsubstituted alkyl group. R can be substituted, for example,
compounds commonly found in liquid electrical air freshen anyWhere along the chain With one or more methyl groups. In
ers. It is also desired to provide compositions that include a one embodiment, X is H. In one embodiment, X is Cl-C3
loW pressureVOC (e. g., DPMA) and a fragrance composition 60 unsubstituted alkyl group.
Wherein the evaporation rate is regulated to Within a prede In one embodiment, the loW vapor pressure VOC potentia
termined period oftime (e.g., 30 days, or 40 days, or 60 days), tor compound is selected from hexyl acetate, 3,3,5-trimeth
during Which at least substantially all of the fragrance is ylhexyl acetate, bomyl formate, 3-hexenyl butyrate, phenyl
effectively evaporated into the surrounding environment, ethyl acetal, butyl hexanoate, isononanol, acetone alcohol,
preferably in a controlled fashion. 65 isoprenyl acetate, isobutyl 2-pentanoate, amyl propionate,
It is thus an object to provide compositions that include one herbal dioxane, furfuryl formate, methyl acetyl acetone, and
or more loW pressure VOC (e.g., DPMA) and one or more a butyl acetoacetate. In one embodiment, the loW vapor pres
 US 8,603,963 B1
3 4
sure VOC potentiator compound is selected from 3,3,5-trim speci?ed at 20° C., in accordance With the convention estab
ethylhexyl acetate and hexyl acetate. lished by the California Air Resources Board (CARB).
In one embodiment, at least 80%, or at least 90% of the As used herein, the term “clogP” refers to the calculated
fragrance composition, by Weight, evaporates Within 30 days, n-octanol/Water partition coe?icient. Preferably, it is calcu
or 60 days, of being maintained at ambient conditions. Pref lated by “Molecular Modeling Pro” softWare (version 6.0.6),
erably, the fragrance composition evaporates in a controlled available from Chem SW, Fair?eld, Calif.
fashion. The evaporation rate can be tailored by a perfumer to In the event that c log P values cannot be calculated using
suit the evaporation rate desired in the particular application. “Molecular Modeling Pro” softWare (version 6.0.6), c log P
A second aspect of the presently disclosed subject matter values can be calculated as disclosed in US. Pat. No. 6,869,
provides a fragrance consumer product (e. g., a electrical liq 923 at col. 3, 11. 18-38, Which is hereby incorporated by
uid air freshener device) that contains any one of the fragrance reference in its entirety. As disclosed therein, clogP values
compositions disclosed herein. can also be calculated by the “C log P” program, available
A third aspect of the presently disclosed subject matter from Daylight CIS. The “calculated log P” (clogP) can also be
provides a method of decreasing the amount of high vapor calculated by the fragment approach of Hansch and Leo (cf.,
pressure VOC solvent in a fragrance composition. This A. Leo, in Comprehensive Medicinal Chemistry, Vol. 4, C.
method includes removing at least a portion of any high vapor Hansch, P. G. Sammens, J. B. Taylor and C. A. Ramsden,
pressure VOC present in the composition (preferably the Eds., p. 295, Pergamon Press, 1990, incorporated herein by
entire amount of hi gh vapor pres sure VOC present), adding at reference). The fragment approach is based on the chemical
least one loW vapor pressure VOC to the composition; and 20 structure of each fragrance component, and takes into account
adding at least one loW vapor pressure VOC potentiator com the numbers and types of atoms, the atom connectivity, and
pound to the composition to provide a loW VOC solvent chemical bonding.
fragrance composition. As used herein, the term “electrical liquid air freshener
device” refers to device or system that includes an electrical
BRIEF DESCRIPTION OF THE DRAWINGS 25 or battery source of energy. The term “electrical liquid air
freshener device includes heated liquid Wick systems, pieZo
For a more complete understanding of various embodi electrical spraying systems, electrospray devices and Venturi
ments of the described subject matter and its advantages, devices, as Well as devices that are poWered by solar or other
reference is noW made to the folloWing description, taken in alternative forms of energy.
conjunction With the accompanying draWings, in Which: 30 As used herein, a fragrance composition evaporates in a
FIG. 1 is an evaporation comparison betWeen the standard controlled fashion When the evaporation rate, measured as
fragrance formulation A', and the LoW Vapor Pressure VOC Weight of fragrance loss, per unit of time (e.g, 0.2-0.6 g/day)
formulation A, as described in Example 1, measured as the over a given time period (e.g., 30, 40 or 60 days) is relatively
amount of Weight loss of fragrance over 40 days. constant over the given time period. In one embodiment, the
FIG. 2 is an evaporation comparison betWeen the standard 35 evaporation rate is relatively constant When the Weight of
fragrance formulation B', and the LoW Vapor Pressure VOC fragrance loss per unit of time differs by less than 15%, or
formulation B, as described in Example 2, measured as the 110% or 120% over the given time period.
amount of Weight loss of fragrance over 40 days. As used herein, the term “fragrance components” refer to
FIG. 3 is an evaporation curve for the fragrance formula components that impart a generally hedonically pleasing fra
tion described in Example 3, measured as the amount of 40 grance and includes both loW vapor pressure VOC potentiator
Weight loss of fragrance over 40 days. compounds and non-loW vapor pressure VOC potentiator
compounds that act as fragrance ingredients. In one embodi
DETAILED DESCRIPTION ment, fragrance components refer to fragrance and ?avor
materials listed in either Allured’s Flavor and Fragrance
As used herein, a “loW vapor pressure VOC” or 45 materials 2004, published by Allured Publishing Inc., the
“LVPVOC” refers to organic solvents or carriers for use in a IFRA (International Fragrance Research Association) data
consumer product containing fragrance materials that have a base, and RIFM (Research Institute of Fragrance Materials)
vapor pressure ofless than (<01 mm Hg at 20° C. database, each of Which and hereby incorporated by reference
As used herein, a “high vapor pressure VOC” or in their entirety.
“HVPVOC” refers to organic solvents or carriers for use in a 50 LoW Vapor Pressure VOCs
consumer product containing fragrance materials that have a As noted above, as used herein, a “loW vapor pressure
vapor pressure greater than or equal to (z) 0.1 mm Hg at 20° VOCs” or “LVPVOC” refers to organic solvents or carriers
C. that have a vapor pressure of less than (<) 0.1 mm Hg at 20°
As used herein, the term “solvent” and “carrier” are used C. LoW vapor pressure VOCs, such as DPMA, have not been
interchangeably and, unless speci?ed otherWise, are gener 55 recogniZed and Widely used, if at all, in liquid electrical air
ally mentioned With respect to a loW vapor pressure VOC or fresheners. When loW vapor pressure VOCs are employed in
high vapor pressure VOC. combination With a composition that includes at least one loW
As used herein, the phrase “consumer product” or “end vapor pressure VOC potentiator compound, the resulting fra
product” refers to composition that is in a form ready for use grance composition achieves performance that meets or
by the consumer for a marketed indication. 60 exceeds the performance of comparable formulations that
As used herein, a “solvent suitable for use in a consumer contain higher vapor pressure VOCs that are subject to
product” is a solvent that, When combined With other compo increasingly stringent environmental regulation. These for
nents of an end product, Will not render the end product un?t mulas are advantageous in that they can be fragranced With a
for its intended consumer use. loW and/or pleasant fragrance pro?le and have a good Weight
Unless speci?ed otherWise, all vapor pressures listed in this 65 loss pro?le, as Well as, loW toxicity issues and none of the
disclosure are the vapor pressure at 25° C. It is noted, hoW VOC problems associated With other carriers that are typi
ever, that the HVPVOC and LVPVOC vapor pressures are cally used in air care applications.
 US 8,603,963 B1
5 6
In one embodiment, a LVPVOC solvent includes only TABLE 1-continued
those solvents that are approved for use by the California Air
Resources Board (CARB) as LVPVOC solvents. Thus, in this Flash Point and Vapor Pressures (at 25° C.)
of LoW Vapor Pressure VOC Potentiator Compounds
particular embodiment, a LVPVOC solvent is a CARB-com
pliant solvent, and excludes non-CARB-compliant solvents. LoW Vapor Pressure CAS Flash Vapor
An example of a loW pressure VOC is dipropylene glycol VOC Potentiator Compound Number Point Pressure
methyl ether acetate (DPMA), Which is commercially avail methyl carbitol 628-99-9 189° F. 0.3 mmHg
able, for example, from DoW Chemical (Midland, Mich.) butyl heptanoate 4948-28-1 188° F. 0.1 mmHg
under the brand name DoWanol® DPMA. lts major isomer is 6-methyl-5-hepten-2-one 123-29-5 188° F. 0.2 mmHg
propylene
represented by the structure beloW: glycol acetal
phenyl acetaldehyde 3913-81-3 188° F. 0.4 mmHg
hexyl isothiocyanate 111-87-5 187° F. 0.1 mmHg
phenyl acetaldehyde dimethyl 5454-28-4 187° F. 0.1 mmHg
acetal
decanal (aldehyde C-10) 67452-27-1 186° F. 0.1 mmHg
methyl nonanoate 112-31-2 186° F. 0.2 mmHg
verbenyl acetate 53398-85-9 185° F. 0.1 mmHg
sorbyl butyrate 35154-45-1 185 ° F. 0.1 mmHg
(E)-4-decen-1-al 33467-79-7 185° F. 0.1 mmHg
2,3-butane diol 72203-98-6 185° F. 0.2 mmHg
According to the vendor, DoWanol® DPMA has a vapor (:)-menthone 16930-93-1 185° F. 0.3 mmHg
20 4-decen-1-al 59471-80-6 185° F. 0.3 mmHg
pressure of 0.08 mmHg at 20° C.
verbenol 21661-97-2 185° F. 2.4 mmHg
Other examples of loW vapor pressure VOC solvents
tetrahydromyrcenyl acetate 65405-70-1 184° F. 0.2 mmHg
include, but are not limited to, DoWanol TPM, DoWanol (E)-2-nonen-1-al 4404-45-9 184° F. 0.3 mmHg
DPNB and other VOCs With a VP less than 0.1 mmHg. The isophorone 54889-48-4 184° F. 0.4 mmHg
use of these solvents in conjunction With a loW vapor pressure ethyl acetoacetate 101 -48-4 184° F. 0.8 mmHg
VOC potentiator compound yield formulations With the com 25 2-nonen-1-al
octanal propylene glycol acetal 74094-61-4
5009-32-5
183°
183°
F.
F.
0.1 mmHg
0.3 mmHg
bined bene?t of technical and hedonic performance that propylene glycol diacetate 34300-94-2 183° F. 0.6 mmHg
exceeds the performance that the loW vapor pressure VOC tetrahydrofurfuryl alcohol 6825 8-95-7 183 ° F. 0.8 mmHg
and loW vapor pressure VOC potentiator compound yield by (Z)-3-hexen-1-yl Z-methyl 78989-37-4 182° F. 0.1 mmHg
themselves. butyrate
30 (E)-isocitra1 53398-83-7 182° F. 0.1 mmHg
In one embodiment, the fragrance composition contains isopropyl octanoate 545 8-59-3 181° F. 0.2 mmHg
from about 1% to about 80%, from about 20% to about 60%, nonan-3-yl acetate 60826-15-5 181° F. 0.2 mmHg
or from about 30% to about 50% by Weight of LVPVOCs methyl benzoate 112-41 -4 181° F. 0.4 mmHg
2-nonanol 78-70-6 180° F. 0.1 mmHg
(e.g., DPMA), based on the total Weight of the fragrance tetrahydrocarvone 6191-71-5 180° F. 0.1 mmHg
composition. 35 propyl 2-furoate 432-25 -7 180° F. 0.3 mmHg
LoW Vapor Pressure VOC Potentiator Compounds acetophenone 68480-08-0 179° F. 0.4 mmHg
LoW vapor pressure VOC potentiator compounds can octanol 6454-22-4 178° F. 0.1 mmHg
include certain fragrance materials selected from primary (E)-3-nonen-2-one 18492-65-4 178° F. 0.3 mmHg
heptanal 2,3-butane diol acetal 67 859-9 6-5 177° F. 0.2 mmHg
alcohols, secondary alcohols, aldehydes, esters, ketones, phe para-tolyl aldehyde 97 890-1 3-6 176° F. 0.3 mmHg
nolic compounds and other recogniZed aromachemical com (E)-2-hexen-1-yl Z-methyl 1731-84-6 175° F. 0.1 mmHg
40 butyrate
pounds that meet the characteristics de?ned beloW. The non
VOC portion of the fragrance composition is constructed in 3-nonanol 626-82-4 175° F. 0.1 mmHg
(Z)-2-pinanol 106-32-1 175° F. 0.1 mmHg
such a Way to achieve a higher than usual volatility, and is (E,E)-2,4-heptadien-1-ol 500-02-7 175 ° F. 0.1 mmHg
particularly Well adapted for use in an electrical liquid elec ethyl (E)-4-octenoate 147-89-91 175° F. 0.2 mmHg
trical air freshener. butyl hexanoate 111-70-6 175° F. 0.2 mmHg
45 3-nonen-2-one 103-09-3 175° F. 0.8 mmHg
In one embodiment, loW vapor pressure VOC potentiator 3 ,3 ,S-trimethylhexyl acetate 5 843 0-94-7 174° F. 0 .2 mmHg
compounds include, but are not limited to, hexyl acetate, (E,E)-2,4-octadien-1-al 123-96-6 174° F. 0.4 mmHg
3,3,5-trimethylhexyl acetate, bornyl formate, 3-hexenyl linalool 513-85-9 173° F. 0.2 mmHg
butyrate, phenyl ethyl acetal, butyl hexanoate, isononanol, ethyl phenyl acetate 111-77-3 172° F. 0.1 mmHg
l-dodecene 104- 87-0 172° F. 0.2 mmHg
acetone alcohol, isoprenyl acetate, isobutyl 2-pentanoate,
50 isocyclocitral 1335-66-6 172° F. 0.3 mmHg
amyl propionate, herbal dioxane, furfuryl formate, methyl ortho-tolyl aldehyde 2463-53-8 171° F. 0.3 mmHg
acetyl acetone, and butyl acetoacetate. In an alternative ethyl nonanoate 589-98-0 170° F. 0.1 mmHg
embodiment, the loW vapor pressure VOC potentiator com beta-cyclocitral 93-89-0 170° F. 0.2 mmHg
pounds are selected from the compounds listed in Table 1, homomenthyl acetate 73757-27-4 170° F. 0.2 mmHg
furfuryl acetone 33467-76-4 170° F. 0.3 mmHg
beloW: (E)-7-methyl-3-octen-2-one 89-80-5 170° F. 0.4 mmHg
55
citronellal 106-23-0 169° F. 0.3 mmHg
TABLE 1 (S)-(—)-citronellal 699-17-2 168° F. 0.2 mmHg
diethyl oxalate 18402-83-0 168° F. 0.4 mmHg
Flash Point and Vapor Pressures (at 25° C.) Z-methyl butyl 3-methyl 108-82-7 167° F. 0.2 mmHg
of LoW Vapor Pressure VOC Potentiator Compounds butenoate
ethyl octanoate 18829-56-6 167° F. 0.2 mmHg
60 dipropylene glycol methyl ether 30390-50-2 166° F. 0.6 mmHg
LoW Vapor Pressure CAS Flash Vapor
VOC Potentiator Compound Number Point Pressure (Z)-4-hepten-1-ol 74410-10-9 165° F. 0.2 mmHg
heptanol 70786-44-6 165° F. 0.2 mmHg
isopulegyl formate 33522-69-9 190° F. 0.1 mmHg heptanal cyclic propylene acetal 529-20-4 165° F. 0.4 mmHg
(Z)-7-decen-1-al 10588-15-5 190° F. 0.1 mmHg (E)-2-hepten-1-yl acetate 615-10-1 165 ° F. 0.5 mmHg
ethyl benzoate 94089-01-7 190° F. 0.3 mmHg (3S,3aS,7aR)-dill ether 89-54-87 164° F. 0.3 mmHg
(E)-2-decen-1-al 101-97-3 190° F. 0.1 mmHg 65 dill ether 1125-88-8 164° F. 0.3 mmHg
4-isopropyl-2-cyclohexenone 624-51-1 189° F. 0.2 mmHg S-methyl furfural 20125-81-9 163° F. 1.9 mmHg
 US 8,603,963 B1
7 8
TABLE l-continued TABLE l-continued
Flash Point and Vapor Pressures (at 25° C.) Flash Point and Vapor Pressures (at 25° C.)
of LoW Vapor Pressure VOC Potentiator Compounds of LoW Vapor Pressure VOC Potentiator Compounds

LoW Vapor Pressure CAS Flash Vapor LoW Vapor Pressure CAS Flash Vapor
VOC Potentiator Compound Number Point Pressure VOC Potentiator Compound Number Point Pressure

(E)-2-heXen-1-yl butyrate 4798-61-2 162° F. 0.2 mmHg 3-methyl cycloheXanone 111-15-9 125° F. 1.5 mmHg
8-nonen-2-one 30361-28-5 161° F. 0.1 mmHg 4-methyl-1-pentanol 473-67-6 125° F. 1.7 mmHg
(Z)-4-hepten-1-al diethyl acetal 93-58-3 160° F. 0.2 mmHg propyl hexanoate 96-41-3 125° F. 2.0 mmHg
isooctyl acetate 122-78-1 160° F. 0.2 mmHg 10 cyclopentanol 592-82-5 124° F. 2.5 mmHg
2-octanol 98-86-2 160° F. 0.2 mmHg 2-isoheXyl alcohol 13877-91-3 123° F. 1.9 mmHg
(Z)-3-hepten-1-yl acetate 1576-78-9 160° F. 0.4 mmHg 2,3,4-trimethyl-3-pentanol 116-09-6 122° F. 1.5 mmHg
1-acetoXyacetone 1120-21-4 160° F. 3.3 mmHg 1,8-cineole 35926-04-6 122° F. 1.9 mmHg
benZaldehyde dimethyl acetal 95-92-1 157° F. 0.4 mmHg ethyl heXanoate 592-20-1 121° F. 1.6 mmHg
ethyl sorbate 33046-81-0 157° F. 0.5 mmHg butyl butyrate 624-54-4 121° F. 1.8 mmHg
2-octen-1-al 50746-10-6 155° F. 0.9 mmHg 15 isopropyl heXanoate 930-68-7 120° F. 1.0 mmHg
amyl butyrate 78-59-1 154° F. 0.6 mmHg amyl alcohol 97-64-3 120° F. 2.2 mmHg
heptyl acetate 928-80-3 154° F. 12.0 mmHg 1-heXen-3-yl acetate 12-07-311 120° F. 3.1 mmHg
2,6-dimethyl-4-heptanol 2396-84-1 151° F. 0.3 mmHg ethyl lactate 142-83-6 120° F. 3.8 mmHg
ethyl heptanoate 67746-30-9 151° F. 0.7 mmHg 4-heptanone 123-19-3 120° F. 6.1 mmHg
butyl isothiocyanate 73545-18-3 151° F 2.6 mmHg
3-octanol 16939-73-4 150° F 0.3 mmHg
(E)-2-heXen-1—aldiethylacetal 34590-94-8 150° F 0.5 mmHg 20 In one embodiment, the 3,3,5-trimethylhexyl acetate is
{Ethyl °°°t°°°°t°t° 544'12'7 150 F 0'9 mmHg obtained as Vanoris from IFF (New York, N.Y.).
heXanal propylene glycol acetal 540-18-1 150° F 0.9 mmHg . .
ethyl 2-methyl-2-pentenoate 623-84-7 150° F 1.4 mmHg Alr Care Devlces ' ~ ~ '
3-mercapto-3-methyl butyl 98-00-0 149° F 0.4 mmHg Any one of the fragrance compositions disclosed herein
fmmate can be used in any air care device, Without limitation. The
furfuryl alcohol 821-55-6 149° F 0.6 mmHg 25 “ . d . ,, . 1 d . b1 f h
211011330116 131671_56_2 1480 R M mmHg term air care evice inc u es any suita e sur ~ace t at
(:)—camphor 76-22-2 148° F. 0.7 mmHg alloWs for at least some evaporation of volatile mater1als.Any
2'h@Ptan°l 106'30'9 148° F- 1-2 mmHg suitable air care device having any suitable siZe, shape, form,
(E)-2-octen-4-ol 30086-02-3 146° F. 0.4 mmHg ? t. b d S .t b1 . d . b
2_Oct6n_4_Ol 141_97_9 1460 R 04 mmHg or con gura ion can e use . ' ui'a e an care evic'es'can e
(E,E)—3,5—octadien—2—one 14309-57-0 146° F. 0.7 mmHg 30 made from any suitable material, including but not limited to:
4-IH@?1yl-3-P@Ht@1t11;1l-%l l 97-99-4 146° F 1-000 mmHg natural materials, man-made materials, ?brous materials,
3-mercapto-3-me y utano 124-13-0 145° F 0.2 mmHg _ ~ ~ _ -_
3_decamne 2363_89_5 1450 F 04 mmHg non ?brous materials, porous materials, non porous materi
2,3,j_trithiahgxane 111.76.; 1450 1: 1_1 mmHg als, and combinations thereof. In certain embodiments, the air
benl?ld?hyde 105-45-3 145° F 1-3 mmHg care devices used herein are ?ameless in character and
2'°°t°n°n° 928'94'9 145 F 1'4 mmHg 35 include any device used for dispensing any type of volatile
ethyl 2-heXenoate 1599-49-1 144° F 1.3 mmHg . 1 1. .d . h h h f
benzyl ?thyl ether 111_27_3 1430 F 09 mmHg matena (cg. ~iqui s) intot e atmosp ere (suc as ragrance,
b6t5.—OCiInC11C 5 39-30-0 143° F 2_7 mmHg deodorant, disinfectant or insecticide active agent). In certain
(E)-4-h@X@H-1-Ol I 928-92-7 142° F 0-9 mmHg non-limiting embodiments, a typical air care device utilizes a
(z)'3'h°x°n'l'yl 1S°V°l°r°t° 928'97'2 140 F 0'1 mmHg combination of a Wick, gel, and/or porous surface, and an
undecane 763-89-3 140° F 0.4 mmHg . . d. 1 .1 1. .d f 1. .d
(Z)_3_h6Xen_1_al methyl acetal 2311464; 1400 F 05 mmHg 40 emanating region to ispense a V0 an e iqui rom a iqui
2-butoxyethanol 60415-61-4 140° F 0.9 mmHg ?uid reservoir.
heXaHOl 99-85-4 140° F 0-9 mmHg Air care devices (such as, Wicking devices) are knoWn for
(E)'3'h°X°n'1'yl°°°t°t° 42474'44'2 140 F 1'2 mmHg dispensing volatile liquids into the atmosphere, such as fra
ethyl (E)-2-methyl-2-pentenoate 3681-82-1 139° F 1.4 mmHg . . . . . .
2_m6thyl_2_mten_1_al 543_49_7 1380 R 03 mmHg grance, deodorant, disinfectant or insecticide active agent. A
(E)—3—hCXCn-1—Ol 1552-67-6 1330 R 09 mmHg 45 typical air care device utilizes a combination of a Wick and
sec-heXyl alcohol 27329-72-7 137° F 1-5 mmHg emanating region to dispense a volatile liquid from a liquid
furtfumlld, th 1 t l
ocana 16 yacea
1233;‘;
- -
g . .
mggmmg
?uidreservoir. Air care devices are described in US. Pat. Nos.
' ~ ~ '

4_6thyl_6_h6pt6n_3_m6 111_13_7 1360 R M mmHg 1,994,932‘, 2,597,195, 2,802,695, 2,804,291, 2,847,976. Ide
(E).g_hepten_l.ol 5365.964) 1350 1: 0_3 mmHg ally, the air care device shouldrequire little or no maintenance
3-heXeH-1-al 1617-40-9 135° F 11-2 mmHg 50 and should perform in a manner that alloWs the volatile mate
.z'ethoxyethyl amate 3054'92'0 135 F 2'3 mmHg rial to be dispensed at a steady and controlled rate into the
isoprenyl acetate 538-86-3 134° F 4.5 mmHg d . d hi1 . . . . . . . .
acetom alcohol 591_24_2 1330 F 30 mmHg esignate area W e maintaining its emission integrity over
amyl propionate 97-95-0 133° F 3.6 mmHg the Me span of the device.
h?Xyl acetate 64187-83-3 132° F 1-3 mmHg In one embodiment, the air care device is an electrical
2'°y°l°h°X°n°n° 10°73'0 132 F 3 '6 mmHg 55 liquid air freshner device. As noted above, the term “electrical
ethyl 2-hyd.roXy-2-methyl 123-66-0 131° F 0.5 mmHg . . . . ,, “ . . . . ,,
butymt? liquid air freshener device or liquid electrical air freshener
ethyl (Eyz-hexenom 626-89-1 131° F 1_3 mmHg refers to device or system that includes an electrical or battery
3-heXel1-l-ol 109-21-7 130° F 0-5 mmHg operated source of energy Which includes heated liquid Wick
(Z)'2'h°X°n'1'°l 470'82'° 130 F 0'9 mmHg delivery systems, pieZoelectrical spraying systems, electro
benZyl methyl ether 620-02-0 130° F 1.5 mmHg d . V . d . C . 1 1 f
?thyl (Dahmmom 105_30_6 1300 F 16 mmHg 60 spray‘ evices~ or ' entun evices. ommercia examp es 0
(E,E)-2,4-heXadien-1-al 4440-65-7 130° F 4_3 mmHg electrical liquid air freshner devices include, but are not lim
m?thyl heptanoate 112-06-1 127° F 1-6 mmHg ited to, Glade® PlugIns® Scented oil, sold by SC Johnson &
valirildehyde Pmpyle“ gly°°l °2°'77'7 127 F 2'3 mmHg Sons;Air Wick Scented Oils, andAir Wick X-Press® Scented
act? a . . . .

2_pentyl butymte 71_41_0 1260 R U mmHg Oils, sold by Reckitt Benckiser, FebreZe Noticeables sold by
Octanal (aldehyde (1.3) 93.014 1250 1: ()9 mmHg 65 Proctor & Gamble Co., Electric HomeAir Fresheners, sold by
gamma-terpinene 74094-60-3 125° F 1.1mmHg the Yankee Candle Co.; and RenuZit Scented Oils, sold by
Henkel AG.
 US 8,603,963 B1
9 10
It has surprisingly been found that the combination of a loW In one embodiment, the total amount of fragrance compo
vapor pressure VOC (e.g., DPMA) and the fragrance compo nents is from about 20% to about 99% by Weight, of the total
sition can yield hedonically pleasing and constant fragrance Weight of the fragrance composition (including any
pro?les When used in an electrical liquid air freshener device. LVPVOCs and HVPVOCs) . Alternatively, the total amount of
Thus, one embodiment of the presently disclosed subject fragrance components is from about 40% to about 80% by
matter provides an electrical liquid air freshener device that Weight, or from about 50% to about 70% by Weight, of the
contains a fragrance composition disclosed herein. total fragrance composition (including any LVPVOC and
The evaporation rate of the fragrance components(s) can be HVPVOCs).
controlled to dispense the fragrance into the surrounding In one embodiment, from about 40 to about 95 Weight
environment over extended periods of time. The perfumer of percent of the fragrance components, based on the total
ordinary skill can modify the fragrance composition to pro Weight of the fragrance components present in the fragrance
vide controlled evaporation into small (e.g., a bath or living composition, have a vapor pressure greater than 0.08 mmHg
room) or large areas (e. g., large commercial and recreational at 250 C. In alternative embodiments, from about 50 to about
spaces). In one embodiment, the presently disclosed fra 85 Weight percent of the fragrance components, or from about
grance compositions evaporate in a controlled fashion. A 60 to about 75 Weight percent of the fragrance components,
fragrance composition evaporates in a controlled fashion based on the total Weight of the fragrance components present
When the evaporation rate, measured as Weight of fragrance in the fragrance composition, have a vapor pressure greater
loss, per unit of time (e.g, 0.2-0.6 g/day) over a given time than 0.08 mmHg at 250 C.
period (e. g., 30, 40 or 60 days) is relatively constant over the 20 In one embodiment, from about 10 to about 40 Weight
given time period. In one embodiment, the evaporation rate is percent of the total fragrance components have a boiling point
relatively constant When the Weight of fragrance loss per unit of greater than or equal to about 2500 C., based on the total
of time differs by less than 15%, or 110% or 120% over the Weight of the fragrance components present in the fragrance
given time period. composition. In an alternative embodiment, from about 10 to
In one embodiment, the presently disclosed fragrance 25 about 20 Weight percent, or to about 30 Weight percent of the
compositions evaporate at a rate of from about 0.2 to about 0.6 total fragrance components have a boiling point of greater
grams per day, over 30, 40 or 60 days. In a still further than or equal to about 2500 C., based on the total Weight of the
embodiment, the evaporation rate (e.g., grams of fragrance fragrance components present in the fragrance composition.
lost per day), over a given time period (30, 40 or 60 days for The presently disclosed compositions can be in the form of
example) varies by less than 15%, or 110% or 120% over the 30 a simple mixture of liquid fragrance components and
given time period. LVPVOC solvents, or can be in an encapsulated form, e.g.,
The use of a loW vapor pressure VOC, as a carrier, and entrapped in a solid matrix that may include Wall-forming and
fragrance compositions of the present application is appli plasticiZing materials such as mono-, di- or trisaccharides,
cable to a Wide variety of products in the fragrance industry natural or modi?ed starches, hydrocolloids, cellulose deriva
including, but not limited to, electrical liquid air freshener 35 tives, polyvinyl acetates, polyvinylalcohols, proteins or pec
devices. Suitable electrical liquid air freshener devices tins. Examples of particularly useful matrix materials
include in Wick type air freshener devices, Which may be fan include, for example, sucrose, glucose, lactose, levulose,
assisted, pieZoelectrical devices, as Well as, other devices fructose, maltose, ribose, dextrose, isomalt, sorbitol, manni
commonly used in the air care arena. A particularly preferred tol, xylitol, lactitol, malitol, pentatol, arabinose, pentose,
air care device that can be used With the fragrance composi 40 xylose, galactose, maltodextrin, dextrin, chemically modi?ed
tions and loW vapor pressure VOC solvents of the present starch, hydrogenated starch hydrolysate, succinylated or
application is disclosed in International Published Applica hydrolysed starch, agar, carrageenan, gum arabic, gum acca
tion No. WO 2009/006582 and US. Design Pat. Nos. D597, cia, tragacanth, alginates, methyl cellulose, carboxymethyl
191 and D608,879. Each of these references are hereby incor cellulose, hydroxyethyl cellulose, hydroxypropylmethyl cel
porated by reference in their entirety. 45 lulose, derivatives, gelatin, agar, alginate and mixtures
Fragrance Components and Fragrance Compositions thereof. Encapsulation techniques are Well-knoWn to persons
The fragrance components that can be used in the fragrance skilled in the art, and may be performed, for instance, using
compositions of the present disclosure include commercially techniques such as spray-drying, agglomeration or extrusion,
available fragrances, preferably, but not limited to, fragrances or coating encapsulation, including coacervation and com
available from Takasago International Corporation, (Tokyo, 50 plex coacervation techniques.
JP). Other sources of liquid or gel fragrance components
include S.C. Johnson Company (Racine, Wis.), Procter & EXAMPLES
Gamble (Cincinnati, Ohio), Reckitt Benckiser (Berkshire,
UK), Givaudan (Geneva, SWitZerland), Firmenich (Geneva, The present application is further described by means of
Switzerland), and International Flavors and Fragrances (NeW 55 the examples, presented beloW, Wherein the abbreviations
York, N.Y.). have the usual meaning in the art.
In one embodiment, the fragrance composition contains
fragrance components (including both loW vapor pressure Example 1
VOC potentiator compounds and standard fragrance materi
als) in Which at least about 5% to about 60,% by Weight, of the 60 A commercially-available fruity fragrance composition is
fragrance components have a c log P value greater than 3, provided With the components shoWn beloW in Table 2 as
more preferably at least about 10% to about 50%, by Weight, Comparative Formulation A. This formulation contains
of the fragrance components have a c log P value greater than greater than 50 Wt % DoWanol DPM Glycol Ether and meth
3 and most preferably at least about 20% to about 40%, by oxy methyl butanol, Which are VOCs that may not comply
Weight, of the fragrance components have a clog P value 65 With the strictest environmental regulations, such as the regu
greater than 3, based on the total Weight of the fragrance lations established by the California Air Resource Board
components present in the fragrance composition. (CARB).
 US 8,603,963 B1
11 12
A formulation With a similar evaporation rate, and olfactive TABLE 2-continued
properties as Comparative FormulationA is desired, yet using
Fragrance Compo itiou A and A’
a loW vapor pressure VOC solvent that complies With the
strictest regulatory standards, (e.g., is CARB compliant). LOW VOC
LOW VOC Carrier Formulation A' is provided that employs Comparative Carrier
DoWanol DMPA (a LVPVOC), instead of DoWanol DPM Formulation Formulation
A Weight A’ Weight
Glycol Ether and methoxy methyl butanol. Formulation A' CAS Parts Per Parts Per
employs 3,5,5-trimethyl hexyl acetate and hexyl acetate as Component Number Thousand Thousand
potentiator compounds. 2(3H)-Furanone, 5- 706-14-9 2.941 2.941
hexyldihydro
TABLE 2 Butanoic acid, 3-oXo-, 141-97-9 2.941 2.941
ethyl ester
Fragrance Composition A and A’ 1,2-Propanediol 57-55-6 2.462 2.462
3-BUTEN-2-ONE, 4- 14901-07-6 2.353 2.353
LOW VOC (2,6,6-TRIMETHYL-1
Comparative Carrier CYCLOHEXEN-1-YL)
Formulation Formulation 4H-Pyran-4-one, 3- 118-71-8 2.353 2.353
A Weight A’ Weight hydroxy-Z-methyl
CAS Parts Per Parts Per Ethanone, l-phenyl- 98-86-2 2.353 2.353
Component Numb er Thousand Thousand LIME OIL DIST NAT N/A 2.353 2.353
METH LAITONE 10% N/A 2.059 2.059
1-HEXANOL,3,5,5- 58430-94-7 314.706 403.943 20 TEC
TRIMETHYL-, ACETATE 3-HEXEN-1-OL, 3681-71-8 1.765 1.765
DOWANOL DPMA 88917-22-0 300.000 ACETATE, (Z)
l-BUTANOL, 3-METHOXY- 56539-66-3 366.451 2-Propenal, 3-phenyl- 104-55-2 1.765 1.765
3-METHYL Butanoic acid, 3-methyl-, 659-70-1 1.471 1.471
Oxiranecarboxylic acid, 3- 77-83-8 70.588 70.588 3-methylbutyl ester
methyl-3-phenyl-, ethyl ester 25 Z-BUTEN-I-ONE, 1- 23726-91-2 1.235 1.235
PROPANOL, 1(OR 2)-(2- 34590-94-8 32.785 (2,6,6-TRIMETHYL-1
METHOXYMETHYL CYCLOHEXEN-1-YL)-,
ETHOXY) (E)
1,6-Octadien-3-ol, 3,7- 78-70-6 32.353 32.353 CYCLOPENTANE- 24851-98-7 1.176 1.176
dimethyl ACETIC ACID, 3
4H-PYRAN-4-ONE, 3- 4940-11-8 16.471 16.471 30 OXO-2-PENTYL-,
ETHYL-3 -HYDROXY METHYL ESTER
CYCLOHEXANOL, 4- 32210-23-4 14.706 14.706 Benzenepropanal, 4- 80-54-6 1.176 1.176
(1 , 1-DIMETHYLETHYL)-, (1,1-dimethylethyl)
ACETATE .alpha.-methyl
3-Buten-2-one, 4-(2,6,6- 127-41-3 14.706 14.706 Phenol, 2-methoXy-4- 97-53-0 1.176 1.176
trimethyl-Z-cyclohexen- 1 (2-propenyl)
35
yl)-, (E) 2,4-CYCLO- 35044-57-6 1.176 1.176
Acetic acid, hexyl ester 142-92-7 10.000 HEXADIENE- 1
Acetic acid, phenylmethyl 140-11-4 9.318 9.318 CARBOXYLIC
ester ACID, 2,6,6
Butanoic acid, ethyl ester 105-54-4 8.824 8. 824 TRIMETHYL-,
Z-BUTANONE, 4-(4- 5471-51-2 8.824 8. 824 ETHYL ESTER
40
HYDROXYPHENYL) 1% or less trace ingredients 9.042 9.042
3-CYCLOHEXENE-1- 67 80 1 -65-4 8.000 8.000
CARBOXALDEHYDE, 1000.000 1000.000
3 ,6-DIMETHYL
Benzaldehyde, 4-hydroxy- 121-33-5 7.647 7.647
3-methoxy Evaporation curves for Comparative Formulation A and
Benzoic acid, 2- 85-91-6 5.882 5.882 45
(methylamino)-, methyl LoW VOC Carrier Formulation A' are shoWn in FIG. 1, mea
ester sured as the amount of Weight loss of the composition. As
Ethanone, 1-(5,6,7,8- 774-55-0 5.882 5.882 shoWn therein, evaporation of the LoW VOC Carrier Formu
tetrahydro-2-naphthalenyl) lation A' over 40 days is similar to that of Comparative For
BUTANOIC ACID, 2- 66576-71-4 4.941 4.941
METHYL-, l-METHYL 50
mulation A, Which is not CARB compliant. Furthermore, a
ETHYL ESTER minimum of 4 of 5 expert “noses” selected LoW VOC Carrier
BUTANOIC ACID, 1,1- 10094-34-5 4.706 4.706 Formulation A' as an olfactive match to the non-compliant
DIMETHYL-2
PHENYLETHYL ESTER Comparative Formulation A.
OILS, ORANGE, SWEET 8008-57-9 4.706 4.706
Benzenemethanol, 4- 104-21-2 4.118 4.118
55 Example 2
methoXy-, acetate
Benzaldehyde 100-52-7 4.118 4.118
Benzaldehyde, 3-ethoxy- 121-32-4 3.824 3.824 A commercially-available herbal fragrance composition is
4-hydroxy provided With the components shoWn beloW in Table 2 as
3-Buten-2-one, 3-methyl- 127-51-5 3.529 3.529 Comparative Formulation B. This formulation contains
4-(2,6,6-trimethyl-2
cycloheXen-1-yl) 60 greater than 50 Wt % DoWanol DPM Glycol Ether and meth
3-HeXen-1-ol, (Z)- 928-96-1 3.529 3.529 oxy methyl butanol, Which are VOCs that may not comply
2(3H)-Furanone, 5- 104-67-6 3.529 3.529 With the strictest environmental regulations, such as the regu
heptyldihydro lations established by the California Air Resource Board
2H-Pyran-2-one, 6- 713-95-1 3.059 3.059
heptyltetrahydro (CARB).
Z-PENTENOIC ACID, 3142-72-1 3 .000 3.000 65 A formulation With a similar evaporation rate, and olfactive
Z-METHYL properties as Comparative Formulation B is desired, yet using
a loW vapor pressure VOC solvent that complies With the
 US 8,603,963 B1
13 14
strictest regulatory standards, (e.g., is CARB compliant). TABLE 3-continued
LOW VOC Carrier Formulation B' is provided that employs
Fragrance Compo ition B and B’
DoWanol DMPA (a LVPVOC), instead of DoWanol DPM
Glycol Ether and methoxy methyl butanol. Formulation B' LOW VOC
employs 3 ,5 ,5 -trimethyl hexyl acetate as a potentiator com- 5 Comparative Carrier
pound~ Formulation
B Weight
Formulation
B’ Weight
CAS Parts Per Parts Per
TABLE 3 Component Number Thousand Thousand
Fragrance Composition B and B’ 10 alpha-,-alpha-,4-trirnethyl-,
acetate
LOW VOC 2,6-Octadien-1-ol, 3,7- 106-24-1 2.951 2.951
Comparative Carrier dirnethyl—, (E)
Formulation Folmulation OILS, CEDARWOOD 8000-27-9 2.843 2.843
B Weight B’ Weight 7-OCTEN-2-OL, 2,6- 18479-58-8 2.459 2.459
CAS Parts Per Parts Per 15 DIMETHYL
Component Number Thousand Thousand Hcptanoic acid, 2- 142-19-3 2-033 2-033
propenyl ester
DOWANOL DPMA 88917-22-0 440.984 2-BUTEN-1-OL, 2- 28219-61-6 1.967 1.967
PROPANOL, 1(OR 2)-(2- 34590-94-8 307.062 ETHYL-4-(2,2,3
METHOXYMETHYL- TRIMETHYL-3
ETHOXY)- CYCLOPENTEN-1-YL)
l-BUTANOL, 3- 56539-66-3 234.479 20 2H-1-BENZOPYRAN-2- 4430-31-3 1.967 1.967
METHOXY-3-METHYL- ONE, OCTAHYDRO
1,6-Octadien-3-ol, 3,7- 115-95-7 127.200 127.200 Propanoic acid, 2-methyl-, 103-60-6 1.967 1.967
dimethyl—, acetate 2-phenoxyethyl ester
l-HEXANOL, 3,5,5- 58430-94-7 1.960 102.727 OILS, CEDARWOOD, 68990-83-0 1.884 1.884
TRIMETHYL-, ACETATE TEXAN
1,6-Octadien-3-ol, 3,7- 78-70-6 84.265 84.114 25 OILS, PATCHOULI 8014-09-3 1.791 1.791
dimethyl- 2(3H)—Furanone, 5- 104-67-6 1.693 1.693
LAVANDIN GROS S XUNK 39 .344 3 9. 344 heptyldihydro
Benzenemethanol, 4- 104-21-2 32.787 32.787 CYCLOHEXANOL, 32210-23-4 1.658 1.658
methoxy—, acetate 4—(1,1-DIMETHYL—
2(3H)-Furanone, 104-61-0 18.057 18.057 ETHYL)-, ACETATE
dihydro-5-pentyl- 30 1,3-Benzodioxole-5- 120-57-0 1.640 1.640
Benzaldehyde, 3- 121-32-4 9.836 9.836 carboxaldehyde
ethoxy-4-hydroxy- 2H-1-Benzopyran-2- 91-64-5 1.640 1.640
METH LAITONE N/A 9.836 9.836 one
10% TEC Bicyclo2.2.lheptan-2- 76-22-2 1.639 1.639
Benzaldehyde, 4- 121-33-5 9.836 9.836 one, 1,7,7-trimethyl
hydroXy-3-methoxy- 35 CYCLOPENTANE- 24851-98-7 1.311 1.311
4H-PYRAN-4-ONE, 4940-11-8 8.197 8.197 ACETIC ACID, 3
3-ETHYL-3- OXO-2-PENTYL-,
HYDROXY- METHYL ESTER
BUTANOIC ACID, 10094-34-5 7.311 7.311 6-OCTEN-1-OL, 3,7- 7540-51-4 1.311 1.311
1,1-DIMETHYL-2- DIMETHYL-, (S)
PHENYLETHYL ESTER 3-Buten-2-one, 3-methyl-4- 127-51-5 1.311 1.311
TERPENES AND 68917-33-9 5.255 5.255 40 (2,6,6-trimethyl
TERPENOIDS, 2-cyclohexen-1-yl)
LEMON-OIL OILS, ROSEMARY 8000-25-7 1.206 1.206
CYCLOHEXANE- 2705-87-5 4.918 4.918 ETHANONE, 1-(5,6,7,8- 21145-77-7 0.984 0.984
PROPANOIC ACID, 2- TETRAHYDRO
PROPENYL ESTER 3,5,5,6,8,8-HEXA
3-CYCLOHEXENE-1- 31906-04-4 4.918 4.918 45 METHYL-2-NAP
CARBOXALDEHYDE, HTHALENYL)
4-(4-HYDROXY- BICYCLO[2.2.1]HEP- 1632-73-1 0.984 0.984
4-METHYLPENTYL)- TAN-2-OL, 1,3 ,3
Acetic acid, phenylmethyl 140- 1 1 —4 4.754 4.754 TRIMETHYL
ester 1,3,4,6,7,8-HEXA- N/A 0.984 0.984
Hexanoic acid, 2-propenyl 123-68-2 4.302 4.302 50 HYDRO—4,6,6,7,8,8—
ester HEXAMETHYL
2H-Pyran-2-one, 6- 713-95-1 3.934 3.934 CYCLOPENTA
heptyltetrahydro- GAMMA-2
BenZaldehyde, 4- 123- 1 1 -5 3 .444 3.444 BENZOPYRAN
methoxy- Butanoic acid, 540-18-1 0.984 0.984
ETHANONE, 1- 54464-5 7-2 3 .279 3.279 55 pentyl ester
(1,2,3,4,5,6,7,8- 2H-Pyran-2-one, 705-86-2 0.984 0.984
OCTAHYDRO-2,3 ,8,8— tetrahydro-6-pentyl
TETRAMETHYL- Decanoic acid 334-48-5 0.885 0.885
2-NAPHTHALENYL)- PROPANOL, OXYBIS- 25265-71-8 0.168 0.876
Butanoic acid, ethyl ester 105-54-4 3 .279 3.279 Octanal, 7-hydroxy- 107-75 -5 0.820 0.820
1,4-Dioxacycloheptadecane- 105-95-3 3 .279 3.279 3,7-dimethyl
5 ,17-dione 60 NAPHTHA 64742-48-9 0.767
LAVENDER OIL, SPIKE 8016-78-2 3 .279 3.279 (PETROLEUM),
TERPENES AND 68647-72-3 3 .279 3.279 HYDROTREATED
TERPENOIDS, SWEET HEAVY
ORANGE-OIL OILS , 8000-48-4 0.755 0.755
OILS, CLARY SAGE 8016-63-5 3.279 3.279 EUCALYPTUS
1,2-Propanediol 57-55-6 3.167 3.167 65 2(3H)-Furanone, 695-06-7 0.677 0.677
3-Cyclohexene-1-methanol, 80-26-2 3 .050 3.050 5-ethyldihydro
 US 8,603,963 B1
16
TABLE 3-continued TABLE 4-continued
Fragrance Composition B and B’ Fragrance Composition C

LOW VOC LOW VOC

Comparative Carrier m Carrier
Formulation Formulation Formulation
B Weight B’ Weight CAS C
CAS Parts Per Parts Per Component Number 1,000 Parts
Component Number Thousand Thousand
REACTION PRODUCTS
Decanal 112-31-2 0.656 0.656 WITH BORON TRIFLUORIDE
1% or less trace ingredients 9.495 9.495 AND 1,5 ,9-TRIMETHYL- 1 ,5,9
CYCLODECATRIEVE
1000.000 1000.000 1,6-Octadien-3-ol, 3,7-dimethyl-, 115-95-7 5.342
acetate
2-BUTEN-1-OL, 2-METHYL-4- 28219-60-5 3 .226
Evaporation curves for Comparative Formulation B and (2,2,3-TRIMETHYL-3
LoW VOC Carrier Formulation B' are shoWn in FIG. 2, mea CYCLOPENTEN-1-YL)
CYCLOPENTANEACETIC ACID, 24851-98-7 3.226
sured as the amount of Weight loss of the composition. As 3-OXO-2-PENTYL-, METHYL
shoWn therein, evaporation of the LoW VOC Carrier Formu ESTER
lation B' over 40 days is similar to that of Comparative For OIL, CHAMPACA 8016-23-7 2.581
1,4-DIOXACYCLO- 549 82-83-1 2.581
mulation B, Which is not CARB compliant. Furthermore, a 20
HEXADECANE-5,16-DIONE
minimum of 4 of 5 expert “noses” selected LoW VOC Carrier 1,6-Octadien-3-ol, 3 ,7-dimethyl- 78-70-6 2.249
Formulation B' as an olfactive match to the non-compliant OILS, MANILA ELEMI 8023-89-0 1.972
6-Octen-1-ol, 3,7-dimethyl- 106-22-9 1.93 6
Comparative Formulation B. 2H-1-BenZopyran-2-one 91 —64-5 1.613
BENZENEPROPANAL, .ALPHA.- 6658-48-6 1.290
Example 3 25 METHYL-4-(2-METHYLPROPYL)
1% or less trace ingredients 9.911
A neW fragrance that is CARB compliant formulation for
use in an electrical liquid air freshener device. It achieves The evaporation curve of LoW VOC Carrier Formulation C
regulatory compliance and loW VOC by preparing the formu is shoWn in FIG. 3.
lation utilizing DPMA as a LVPVOC solvent or carrier. DoW 30 The use of such examples is illustrative only and in no Way
anol DPNB and DoWanol TPM glycol ether have been previ limits the scope and meaning of the invention or of any
ously utilized. exempli?ed term or phrase used herein. Likewise, the inven
tion is not limited to any particular preferred embodiments
TABLE 4 described herein. Indeed, many modi?cations and variations
35 of the invention Will be apparent to those skilled in the art
Fragrance Composition C
upon reading this speci?cation.
LOW VOC It is further to be understood that all values are approxi
Carrier mate, and are provided for description.
Formulation
CAS C
Patents, patent applications, publications, product descrip
40
Component Number 1,000 Parts tions, and protocols are cited throughout this application, the
disclosures of each of Which is incorporated herein by refer
DOWANOL DPMA 88917-22-0 245.161
ence in their entirety for all purposes.
2-PROPANOL, 1-(2-BUTOXY-1- 29911-28-2 245.161
METHYLETHOXY) What is claimed is:
PROPANOL, [2-(2- 25498-49-1 245.161
METHOXYMETHYL 45 1. An air care device comprising a fragrance composition
ETHOXY)METHYLETHOXY] comprising a loW vapor pressure VOC in an amount of from
l-HEXANOL, 3,5 ,5-TRIMETHYL-, 58430-94-7 77.145 about 20% to about 60% by Weight, and at least one loW vapor
ACETATE
ETHANONE, 1-(1,2,3,4,5,6,7,8- 54464-57-2 62.903
pressure VOC potentiator compound, Wherein the composi
OCTAHYDRO-2,3 ,8,8 tion has an evaporation rate of from about 0.2 grams/day to
TETRAMETHYL-2 50 about 0.6 grams/ day that is relatively constant for at least 30
NAPHTHALENYL) days, and Wherein the air care device is a Wicking device or an
2-BUTANOL, 1[[2-(1,1- 139504-68-0 25.806 electrical device.
DIMETHYLETHYL)CYCLO
HEXYL]OXY] 2. The air care device of claim 1, Wherein the fragrance
1,6-NONADIEN-3-OL, 3,7- 10339-55-6 16.129 composition comprises at least 10 Wt % of the least one loW
DIMETHYL 55 vapor pres sure VOC potentiator compound.
1H-3A,7-METHANOAZULENE, 19870-74-7 12.903 3. The air care device of claim 1, Wherein the fragrance
OCTAHYDRO-6-METHOXY-3,6,8,8
TETRAMETHYL-, [3R-(3.ALPHA., composition comprises at least 20 Wt % of the least one loW
3A.BETA.,6.BETA.,7.BETA., vapor pres sure VOC potentiator compound.
8A.ALPHA.)] 4. The air care device of claim 1, Wherein the composition
3-CYCLOPENTENE-l-BUTANOL, 65113-99-7 7.742
.ALPHA. ,.BETA. ,2,2,3
60 has an evaporation rate of from about 0.2 grams/ day to about
PENTAMETHYL 0.6 grams/day that is relatively constant for at least 40 days.
TERPENES AND TERPENOIDS, 68917-33-9 6.606 5. The air care device of claim 1, Wherein the loW vapor
LEMON-OIL pressure VOC is dipropylene glycol methyl ether acetate.
Benzenepropanal, 4-(1,1- 80-54-6 6.452
dimethylethyl)-.alpha.-methyl 6. The air care device of claim 1, Wherein the at least one
Benzeneethanol 60-12-8 6.452 65 loW vapor pressure VOC potentiator compound has a vapor
ACETIC ACID, ANHYDRIDE, 144020-22-4 6.452 pressure, at 25° C., of at least about 0.2 mm Hg and a ?ash
point from about 110° F. to about 200° F.
 US 8,603,963 B1
17 18
7. The air care device of claim 6, wherein the at least one 11. The air care device of claim 10, Wherein R is a C6
loW vapor pressure VOC potentiator compound has a vapor substituted or unsubstituted alkyl group.
pressure, at 25° C., of at least about 0.5 mm Hg and a ?ash 12. The air care device of claim 9, Wherein R is substituted
point from about 120° F. to about 190° F. With one or more methyl groups.
8. The air care device of claim 6, Wherein the at least one 5 13. The air care device of claim 12, Wherein the at least one
loW vapor pressure VOC potentiator compound is selected
loW vapor pressure VOC potentiator compound has a vapor
from the group consisting of 3,3,5-trimethylhexyl acetate,
pressure, at 25° C., ofat least about 1 mm Hg and a ?ash point
hexyl acetate, and combinations thereof.
from about 130° F. to about 180° F. 14. The air care device of claim 1, Wherein the at least one
9. The air care device of claim 1, Wherein the at least one loW vapor pressure VOC potentiator compound is selected
loW vapor pressure VOC potentiator compound is represented 10 from the group consisting of hexyl acetate, 3,3,5-trimethyl
by the formula: hexyl acetate, bornyl forrnate, 3-hexenyl butyrate, phenyl
ethyl acetal, butyl hexanoate, isononanol, acetone alcohol,
isoprenyl acetate, isobutyl 2-pentanoate, amyl propionate,
herbal dioxane, furfuryl forrnate, methyl acetyl acetone, butyl
acetoacetate, and combinations thereof.
R \o iv. 15. The air care device of claim 2, Wherein at least 80% of
the fragrance composition evaporates Within 30 days of being
Wherein maintained at ambient conditions.
R is a Cl-Cl0 substituted or unsubstituted alkyl, alkenyl 20 16. The air care device of claim 1, Wherein the composition
group, or a C4-C8 substituted or unsubstituted cycloalkyl
has an evaporation rate of from about 0.2 grams/ day to about
or aryl group; and 0.6 grams/day that is relatively constant for at least 60 days.
X is hydrogen, or a C l-C5 unsubstituted alkyl group. 17. The product air care device of claim 1, Wherein the air
10. The air care device of claim 9, Wherein R is a C4-C8 care device is an electrical liquid air freshener.
substituted or unsubstituted alkyl group. * * * * *