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Patent 2307214 Summary

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Claims and Abstract availability

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(12) Patent: (11) CA 2307214
(54) English Title: PREVENTING OFF-FLAVOR IN CERTAIN CARAMEL-COLORED BEVERAGES
(54) French Title: PREVENTION DES SAVEURS ANORMALES DANS CERTAINES BOISSONS CARAMEL
Status: Expired and beyond the Period of Reversal
Bibliographic Data
(51) International Patent Classification (IPC):
  • A23L 2/42 (2006.01)
  • A23L 2/58 (2006.01)
  • A23L 2/60 (2006.01)
  • A23L 5/20 (2016.01)
  • A23L 5/40 (2016.01)
(72) Inventors :
  • HAY, BRUCE A. (United States of America)
  • WATKINS, EDWARD K. (United States of America)
(73) Owners :
  • DANISCO USA INC.
(71) Applicants :
  • DANISCO USA INC. (United States of America)
(74) Agent: GOWLING WLG (CANADA) LLP
(74) Associate agent:
(45) Issued: 2004-09-21
(86) PCT Filing Date: 1997-10-29
(87) Open to Public Inspection: 1999-05-06
Examination requested: 2000-06-29
Availability of licence: N/A
Dedicated to the Public: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): Yes
(86) PCT Filing Number: PCT/US1997/019222
(87) International Publication Number: WO 1999021441
(85) National Entry: 2000-04-25

(30) Application Priority Data: None

Abstracts

English Abstract


The present invention is directed to a process for the minimization of the
development of off flavor or off odor in caramel colored
beverages by hydrogenation of the caramel color prior to incorporation into
the beverage.


French Abstract

Cette invention se rapporte à un procédé permettant de réduire au minimum le développement de saveurs anormales ou d'odeurs anormales dans des boissons caramel par hydrogénation du caramel avant son incorporation dans la boisson.

Claims

Note: Claims are shown in the official language in which they were submitted.


-7-
CLAIMS
1. A process for the reduction of off-flavor or off-odor associated with the
use of caramel color in beverages comprising hydrogenation of the caramel
color prior to
incorporation into the beverages to a degree sufficient to reduce said off-
flavor or said
off-odor, and incorporating the hydrogenated caramel color into a beverage.
2. A process according to claim 1 wherein said beverage is cola-flavored.
3. A process according to claim 1 wherein said caramel color is initially in
the form of a powder.
4. A process according to claim 1 wherein said caramel color is in the form
of an aqueous solution.
5. A process according to claim 1 whereby said hydrogenation of the
caramel color is effected in aqueous solution in the presence of a supported
or
unsupported catalyst selected from the group consisting of palladium,
platinum,
ruthenium, rhodium and nickel at a pressure of from about 1 to about 300
atmospheres
and at a temperature of from about 0° to abort 100°C.
6. A process according to claim 1 wherein said hydrogenation of the caramel
color is effected in aqueous solution in the presence of a palladium on carbon
catalyst at
a pressure of from about 1 to about 5 atmospheres and at a temperature of from
about 25°
to about 50°C.
7. A process according to claim 1 wherein said caramel color is added to a
cola-flavored beverage in combination with a high-intensity sweetener.
8. A process according to claim 7 wherein said high-intensity sweetener is
selected from the group consisting of alitame, aspartame, acesulfame-K,
saccharin,
cyclamates, and sucralose.
9. A process according to claim 8 wherein said high intensity sweetener is
alitame.
10. A process according to claim 1 wherein said beverage further contains
non-hydrogenated caramel.
11. A cola-flavored beverage having incorporated herein hydrogenated
caramel color.
12. A cola-flavored beverage according to claim I L wherein said cola-
flavored beverage is carbonated.

-8-
13. A cola-flavored beverage according to claim, 11 wherein said cola-
flavored beverage is not carbonated.
14. A cola-flavored beverage according to claim 11 further containing a high-
intensity sweetener.
15. A cola-flavored beverage according to claim 14 wherein said high-
intensity sweetener is selected from the group consisting of alitame,
aspartame,
acesulfame-K, saccharin, cyclamates, and sucralose.
16. A process for the reduction of off-flavor or off-odor generated from the
combination of caramel color and alitame in cola-flavored carbonated beveragas
comprising hydrogenation of the caramel color prior to incorporation into the
cola
flavored beverage to a degree sufficient to reduce said off-odor.

Description

Note: Descriptions are shown in the official language in which they were submitted.


CA 02307214 2000-04-25
WO 99/21441 PCT/US97/19222
-1-
PREVENTING OFF-FLAVOR IN CERTAIN CARAMEL-' COLORED BEVERAC,ES
Bacfcground of the Invention
The present invention is directed to caramel colored beverages, particularly
carbonated beverages in which the development of off-flavor has been avoided
or
minimized by hydrogenation of the caramel color; and to the method of avoiding
or
minimizing the development of said off-flavor in said beverages.
The present invention is directed particularly to caramel colored beverages
which have been sweetened with alitame.
Alitame is the generic name which has been assigned to 3-(L-aspartyl-D-
alaninamida)-2,2,4,4-tetramethylthietane), a high-intensity sweetening agent
earlier
described by Brennan et al., U.S. Patent 4,471,925. In the field of
artificially-sweetened
beverages, retention of sweetness and of the original flavor on storage are of
utmost
importance. The consumer develops a preference for the particular flavor of a
particular
beverage, and will frequently find any perceptible deviation in that flavor
unacceptable.
Alitame meets the first of these criteria, retention of sweetness, very well.
However, we --
have now employed a highly sensitive sensory panel test which demonstrates
that in
certain alitame sweetened acidic beverages containing caramel, SuCri ~, wa
beverages, therQ is a temperature/time dependent development of an off-flavor,
detected by odor after storage (generally at elevated temperatures to
accelerate the
effects of normal storage conditions).
Summary of the Invention
In one embodiment, the present invention is directed to a process for the
reduction of off flavor or off odor associated with the use of caramel color
in beverages
comprising ;vydrogenation of floe caramel color prior to incorporation into
the beverages
to a degree sufficient to reduce said off flavor or said off odor.
Preferred is a process wherein said beverage is cola-flavored.
Also preferred is a process wherein said caramel color is initially in the
form of
a.powder.
Especially preferred is a process wherein said caramel color is in the form of
an
aqueous solution.
Also especially preferred is a process wherein said hydrogenation of the
caramel
color is effected in aqueous solution in the presence of a palladium on carbon
catalyst
SUBSTITUTE SHEET (RULE 26)

CA 02307214 2000-04-25
WO 99/21441 PCT/US97/19222
_2_
at a pressure of from about 1 to about 5 atmospheres and at a temperature of
from
about 25 ° to about 50° C.
Further preferred is a process wherein said caramel color is added to a cola-
flavored beverage in combination with a high-intensity sweetener.
Especially preferred is a process wherein said high-intensity sweetener is
selected from the group consisting of alitame, aspartame, acesulfame-K,
saccharin,
cyclamates, and sucralose.
Also especially preferred is a process wherein said high-intensity sweetener
is
alitame.
Also especially further preferred is a process wherein said coca-flavored
beverage further contains non-hydrogenated caramel.
In another embodiment, -the present invention is directed to a cola-flavored
beverage having incorporated therein hydrogenated caramel color.
Preferred is a cola-flavored beverage wherein said cola-flavored beverage is
carbanated.
Further preferred is a cola-flavored beverage wherein said cc:la-flavored
beverage is not carbonated.
Further preferred are cola-flavored beverages having incorporated thereinin
artificial sweeteners wish preferred artificial sweetener selected from the
group
consisting of alitane, aspartame, acesulfame-K, cyclamates, saccharin, and
sucralose.
Further preferred is a process for the reduction of off odor generated from
the
combination of caramel color and alitame in cola-flavored carbonated beverages
comprising hydrogenation of the caramel color prior to incorporation info the
cola-
flavored beverage to a degree sufficient to reduce said off odor.
In ~.nother embodiment, the present invention is also directed to
hy:jrogenated
caramel.
~etailed Description of the Invention
The present invention is readily carried out. The caramel color is
hy~~irogenated
prior to incorporation into the beverage. The caramel color initially may be
in the form
3C of a powder or an aqueous solution.
The hydrogenation may be effected under a range of conditions, with preferred
conditions being in aqueous solution in the presence of palladium on carbon
catalyst
~BSTITUTE SHEET (RULE 26)

CA 02307214 2000-04-25
WO 99/21441 PCT/US97/19222
at a pressure of from about 1 to 5 atmospheres and at a temperature of from
about
25°C tv about 50°C.
The process of the present invention is particularly suited to cola-flavored
beverages which have been sweetened with a high-intensity sweetener. The high-
s intensity sweetener may be alitame, aspartame, acesulfame-K, saccharin,
cyclamates,
or sucraiose.
Having described the invention in general terms, reference is now made to
specific examples. It is to be understood that these examples are not meant to
limit the
present invention, the scope of which is determined by the appended claims.
Example 1
Evaluation in Simulated Cola b~Trianale Difference Test
Simulated colas containing citrate, phosphate, benzoate, caffeine, flavor
oils,
antifoam, caramel (either hydrogenated or untreated), and , 45 ppm of alitame
2.5
hydrate were stored at 120°F. Control colas of the same composition but
without
alitame were also held at the same temperature. At various times, a test cola
and a
control cola'were withdrawn for sensory evaluation in a triangle difference
test (M.
Meilgaard, G. V. Civille, and B. T. Carr, 'Sensory Evaluation Techniques," 2nd
Edition,
CRC Press, 8oca Raton, FL, 1991; pages 60-fi7). Three randomly coded samples
were
presented to 12 panelists, with each panelist receiving either two samples of
control
cola and one sample of test cola or one sample of control cola and two samples
of test
cola. Each panelist was asked to identify the odd sample according to the
following
instructions: 'Sniff the samples in the order shown. Two samples are exactly
the same;
one is different. Which of the three samples is different from the other two?
If you are
not sure, take a guess.' N 8 or more of the twelve panelists correctly
identfied the odd
sample, then the alitame-sweetened cola was considered to have been identified
at the
9596 confidence level and the caramel treatment method (if any) was considered
to
have been ineffective.
Example Z
Evafuatlon In Simulated Cola by Preference-Difference Test
Simulated colas prepared and stored as in Example 1 were evaluated by a
standard preference-difference test (M. Meilgaard, G. V. Civille, and B. T.
Carr, "Sensory
Evaluation Techniques,' 2nd Edition, CRC Press, Boca Raton, FL, 1991; page 211
).
Randomly coded samples of the control cola and the test cola were presented to
30
SUBSTITUTE SHEET (RULE 26)

CA 02307214 2003-02-06
WO 99/21x41 PCTlUS97I1922~
-4-
panelists. Each panelist was asked to identify the preferred sample according
to the
following instructions: "Please indicate your preference of the aroma only. if
you do not
have a preference, then mark the No Preference oox,' Results were tabulated as
follows: A = Number of panelists who prefer the control cola (without
alitame); B =
S number of panelists who prefer the test cola (with alitame); C = number of
panelists
indicating No Preference. If C was greater than A minus B, then the colas were
considered to be indistinguishable, and the caramel treatment method (if any)
was
considered to have been effective.
Example 3
Hydroc7enation of Caramel Color
A solution of 250 grams of Sethness'~ 1 y KDS double strength acid-proof
caramel color diluted to 500 milliIi#ers with distilled water was stirred
under hydrogen
at atmospheric pressure with 25 grams of 1096 palladium on carton catalyst for
1 hour
at room temperature. The mixture was filtered through diatomite filterafd
~icafite,
Grefco, Inc.j, the filter cape was washed wi#h distilled water, and the
combined filtrates
were diluted to 1000 mifiiiiters with distilled water.
ExamQIe 4
Hydrogenation of Caramel Color
Undiluted Sethness~ 11 KDS double strength acid-proof caramel color (2000
grams) was stirred under hydrogen at atmospheric pressure with 50 grams of 10~
palladium on carbon catalyst for 1 hour at 50°C, and the mixture was
filtered through
diatomite filteraid (Dicalite, Grefco, Inc.j. Colas prepared with the
hydrogenated
caramel and untreated caramel were stored at 120°1= and evaluated by
the procedure
of Example 1. After 3 days and also afiter 6 days, the odd sample was detected
at the
95~ confidence level in the cola containing untreated caramel, but not in the
cola
containing hydrogenated caramel.
F~camole
H~d,r~ogenatian of Caramel Golot
Undiluted Sethness~ 11 KDS double strength acid-proof caramel calor (1000
grams) was stirred under hydrogen ai aimospl7eric pressure with 100 grams of
596
palladium an carbon catalyst for 1 hour at 50°C, and the mixture was
filtered through
diatomite fifteraid (Dicalite, Grefco, Jnc.j. - Colas prepared with the
nyarogenaiea
caramel and untreated caramel were stored a# 1 ~0 ° F and evaluated by
the procedure
1~c Trade-mark
SUBSTITUTE SHEET ~FtULE 28j

CA 02307214 2000-04-25
WO 99/21441 PCT/US97/19222
of Example 1. After 3 days, and also after 6 days, the odd sample was detected
at the
9596 confidence level in the cola containing untreated caramel, but not in the
cola
containing hydrogenated caramel. After 9 days, the odd sample was detected at
the
95~ confidence level in the cola containing untreated caramel, but not in the
cola
containing hydrogenated caramel.
Examele 6
Hvdroaenation of Caramel Color
A solution of 50 grams of Sethness~ 11 KDS double strength acid-proof
caramel color diluted to 100 milliliters with distilled water was stirred
under hydrogen
at atmospheric pressure with 5 grams of 1096 palladium on carbon catalyst for
1 hour
at room temperature. The mixture was filtered through diatomite filteraid
(Dicalite,
Grefco, Inc.), the filter cake was washed with distilled water, and the
combined filtrates
were diluted to 200 milliliters with distilled water. Colas prepared with the
hydrogenated
caramel and untreated caramel were stored at 120°F and evaluated by the
procedure
of Example 1. After 4 days, after 7 days, and also after 9 days, the odd
sample was,-
detected at the 9596 confidence level in the cola containing untreated
caramel, btrt not
in the cola containing hydrogenated caramel.
Example 7
HydroQenation of Caramel Color
A solution of 5 grams of Sethness~ 11 KDS double strength acid-proof caramel
color diluted to 50 milliliters with distilled water was shaken at room
temperature with
1 gram of 5°o palladium on carbon catalyst under a hydrogen pressure 50
psi above
atmospheric for 30 minutes, and the mixture was filtered through diatomite
filteraid
(Dicalite, Grefco, inc.).
ExartiplE a
Hydro4enation of Caramel Color
A solution of 5 grams of Sethness~ 11 KDS double strength acid-proof caramel
color diluted to 50 milliliters with distilled water was shaken at room
temperature with
0.5 gram of 596 palladium on carbon catalyst under a hydrogen pressure 10 psi
above
atmospheric for 5 minutes, and the mixture was filtered through diatomite
filteraid
(Dicalite, Grefco, Inc.).
SUBSTITUTE SHEET (RULE 26)

CA 02307214 2000-04-25
WO 99/21441 PCT/US97/19222
-g-
Example 9
Hydro4enation of Caramel Color
Undiluted Williamson~ 11 KDS caramel color (1000 grams) was shaken at room
temperature with 50 grams of 1096 palladium on carbon catalyst under a
hydrogen
pressure 50 psi above atmospheric for 18 hours, and the mixture was filtered
through
diatomite filte~aid (Dicalite, Grefco, Inc.). Colas prepared with the
hydrogenated
caramel were stored at 120°F and evaluated by the procedure of Example
2. After 7
days and also after 14 days, the No Preference number (C) was larger than A
minus
B, indicating that the samples were indistinguishable and that the caramel
treatment
was effective.
SUBSTITUTE SHEET (RULE 26)

Representative Drawing

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Administrative Status

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Event History

Description Date
Inactive: IPC deactivated 2016-03-12
Inactive: IPC deactivated 2016-03-12
Inactive: IPC from PCS 2016-01-09
Inactive: IPC from PCS 2016-01-09
Inactive: IPC expired 2016-01-01
Inactive: IPC expired 2016-01-01
Time Limit for Reversal Expired 2008-10-29
Letter Sent 2007-10-29
Inactive: IPC from MCD 2006-03-12
Inactive: IPC from MCD 2006-03-12
Inactive: IPC from MCD 2006-03-12
Grant by Issuance 2004-09-21
Inactive: Cover page published 2004-09-20
Inactive: Final fee received 2004-07-13
Pre-grant 2004-07-13
Letter Sent 2004-03-30
Letter Sent 2004-03-30
Letter Sent 2004-03-30
Inactive: Single transfer 2004-02-06
Notice of Allowance is Issued 2004-01-16
Notice of Allowance is Issued 2004-01-16
Letter Sent 2004-01-16
Inactive: Approved for allowance (AFA) 2003-12-30
Amendment Received - Voluntary Amendment 2003-02-06
Inactive: S.30(2) Rules - Examiner requisition 2002-08-08
Inactive: Correspondence - Transfer 2001-06-22
Letter Sent 2001-06-15
Letter Sent 2001-06-15
Letter Sent 2001-06-15
Letter Sent 2001-06-15
Inactive: Single transfer 2001-04-25
Letter Sent 2000-07-26
Inactive: Cover page published 2000-07-14
Request for Examination Received 2000-06-29
Request for Examination Requirements Determined Compliant 2000-06-29
All Requirements for Examination Determined Compliant 2000-06-29
Inactive: First IPC assigned 2000-06-29
Inactive: Courtesy letter - Evidence 2000-06-13
Inactive: Notice - National entry - No RFE 2000-06-07
Application Received - PCT 2000-06-06
Application Published (Open to Public Inspection) 1999-05-06

Abandonment History

There is no abandonment history.

Maintenance Fee

The last payment was received on 2003-10-10

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Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
DANISCO USA INC.
Past Owners on Record
BRUCE A. HAY
EDWARD K. WATKINS
Past Owners that do not appear in the "Owners on Record" listing will appear in other documentation within the application.
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Document
Description 
Date
(yyyy-mm-dd) 
Number of pages   Size of Image (KB) 
Description 2003-02-06 6 294
Abstract 2000-04-25 1 33
Description 2000-04-25 6 286
Claims 2000-04-25 2 65
Cover Page 2000-07-14 1 24
Claims 2000-04-26 2 69
Cover Page 2004-08-19 1 25
Notice of National Entry 2000-06-07 1 192
Acknowledgement of Request for Examination 2000-07-26 1 177
Request for evidence or missing transfer 2001-04-26 1 108
Courtesy - Certificate of registration (related document(s)) 2001-06-15 1 112
Courtesy - Certificate of registration (related document(s)) 2001-06-15 1 112
Courtesy - Certificate of registration (related document(s)) 2001-06-15 1 112
Courtesy - Certificate of registration (related document(s)) 2001-06-15 1 112
Commissioner's Notice - Application Found Allowable 2004-01-16 1 161
Courtesy - Certificate of registration (related document(s)) 2004-03-30 1 105
Courtesy - Certificate of registration (related document(s)) 2004-03-30 1 105
Courtesy - Certificate of registration (related document(s)) 2004-03-30 1 105
Maintenance Fee Notice 2007-12-10 1 173
Correspondence 2000-06-07 1 15
PCT 2000-04-25 9 326
PCT 2000-04-26 4 137
Fees 2001-10-29 1 25
Fees 2000-10-30 1 27
Correspondence 2004-07-13 1 32