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Patent 2122907 Summary

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(12) Patent Application: (11) CA 2122907
(54) English Title: VEGETABLE OIL COMPOSITIONS
(54) French Title: COMPOSITIONS D'HUILES VEGETALES
Status: Dead
Bibliographic Data
(51) International Patent Classification (IPC):
  • C11B 5/00 (2006.01)
  • A23D 9/00 (2006.01)
(72) Inventors :
  • CARRICK, VIRGINIA (United States of America)
  • YODICE, RICHARD (United States of America)
(73) Owners :
  • AC HUMKO CORP. (United States of America)
(71) Applicants :
(74) Agent: SMART & BIGGAR
(74) Associate agent:
(45) Issued:
(86) PCT Filing Date: 1992-03-09
(87) Open to Public Inspection: 1993-09-16
Examination requested: 1997-06-19
Availability of licence: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): Yes
(86) PCT Filing Number: PCT/US1992/000702
(87) International Publication Number: WO1993/017566
(85) National Entry: 1994-05-04

(30) Application Priority Data: None

Abstracts

English Abstract


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ABSTRACT OF THE INVENTION
The present invention deals with stabilizing triglycer-
ide oils of high oleic content through the use of tocopherol.
This combination of the high oleic oil and the tocopherol
results in a surprisingly stable composition for use in deep
frying.


Claims

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


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Case 2535R

What is claimed is:
1. A natural vegetable oil composition comprising tri-
glycerides wherein at least about 70% of the fatty acid moi-
eties in the triglyceride are oleic; less than about 20% of
the fatty acid moieties in the triglyceride are linoleic, and
further comprising at least about 100 ppm of a tocopherol
based on the weight of the triglyceride.
2. The composition of claim 1 wherein the tocopherol
is a naturally occurring tocopherol.
3. The composition of claim 1 wherein the tocopherol
is a gamma tocopherol.
4. The composition of claim 1 wherein the tocopherol
is an alpha tocopherol.
5. The composition of claim 1 wherein the tocopherol
is a d,1-alpha tocopherol.
6. The composition of claim 1 wherein the tocopherol
is present at about 300-3,500 ppm.
7. The composition of claim 1 wherein the tocopherol
is a delta tocopherol.
8. The composition of claim 1 wherein the tocopherol
is a beta tocopherol.
9, The composition of claim 1 wherein the tocopherol
is present as a salt or ester.
10. The composition of claim 1 wherein the tocopherol
is present as an ester of gamma tocopherol.
11. The composition of claim 1 wherein at least about
80% of the fatty acid moieties in the triglyceride are oleic.
12. The composition of claim 1 wherein at least about
85% of the fatty acid moieties in the triglyceride are oleic.
13. The composition of claim 1 wherein less than about
10% of the fatty acid moieties in the triglyceride are
linoleic.
14. The composition of claim 12 wherein the tocopherol
is gamma tocopherol.
15. The composition of claim 1 wherein the vegetable

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oil is substantially free of trans-unsaturated moieties.
16. The composition of claim 1 wherein the linoleic
acid content is less than about 3%.
17. A triglyceride composition wherein at least about
83% of the fatty acid moieties in the triglyceride are oleic
and further including in said composition about 500 to about
3,000 ppm of tocopherol per part of triglyceride.
18. The composition of claim 17 wherein the predominant
triglyceride source is selected from the group consisting of
sunflower oil, soya oil, corn oil, safflower and rapeseed oil
and mixtures thereof.
19. The composition of claim 17 wherein less than about
5% of the fatty acid moieties in the triglyceride are
linoleic.
20. The composition of claim 17 which is substantially
free of hydrogenated oils.
21. The composition of claim 17 wherein the vegetable
oil is substantially free of trans-unsaturated moieties.
22. The composition of claim 17 wherein the linoleic
acid content is less than about 3%.
23. The composition of claim 17 wherein the tocopherol
is a mixture of alpha and gamma tocopherol.
24. The vegetable oil composition of claim 17 wherein
the tocopherol is at least two of alpha, beta and delta
tocopherol.
25. The triglyceride composition of claim 18 wherein
the predominant triglyceride is sunflower oil.
26. The triglyceride composition of claim 18 wherein
the predominant triglyceride is safflower oil.
27. The triglyceride composition of claim 18 wherein
the predominant triglyceride is rapeseed oil.
28. A natural vegetable oil composition comprising tri-
glycerides wherein at least about 70% of the fatty acid moi-
eties in the triglyceride are oleic; less than about 20% of
the fatty acid moieties in the triglyceride are linoleic, and
further comprising an antioxidant effective amount of a to-
copherol.

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28. The composition of claim 28 wherein the tocopherol
is a naturally occurring tocopherol.
29. The composition of claim 28 wherein the tocopherol
is a gamma tocopherol.
30. The composition of claim 28 wherein the tocopherol
is an alpha tocopherol.
31. The composition of claim 28 wherein the tocopherol
is a d,1-alpha tocopherol.
32. The composition of claim 28 wherein the oil is se-
lected from the group consisting of rapeseed oil, safflower
oil, and sunflower oil and mixtures thereof.
33. The composition of claim 28 wherein the tocopherol
is a delta tocopherol.
34. The composition of claim 28 wherein the tocopherol
is a beta tocopherol.
35. The composition of claim 28 wherein the tocopherol
is present as a salt or ester.
36. The composition of claim 28 wherein the tocopherol
is present as an ester of gamma tocopherol.
37. The composition of claim 28 wherein at least about
80% of the fatty acid moieties in the triglyceride are oleic.
38. The composition of claim 28 wherein at least about
87% of the fatty acid moieties in the triglyceride are oleic.
39. The composition of claim 28 wherein less than about
10% of the fatty acid moieties in the triglyceride are
linoleic.
40. A triglyceride composition wherein less than about
15% of the fatty acid moieties in the triglyceride are lino-
leic and further including in said composition about 500 to
about 3,000 ppm of tocopherol per part of triglyceride.
41. The composition of claim 40 selected from the group
consisting of sunflower oil, soya oil, corn oil, sunflower
and rapeseed oil and mixtures thereof.
42. The composition of claim 40 wherein less than about
5% of the fatty acid moieties in the triglyceride are
linoleic.
43. The composition of claim 40 which is substantially

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free of hydrogenated oils.
44. The composition of claim 40 wherein the vegetable
oil is substantially free of trans-unsaturated moieties.
45. The triglyceride composition of claim 40 wherein
the linoleic acid content is less than about 3%.
46. The vegetable oil composition of claim 40 wherein
the tocopherol is a mixture of alpha and gamma tocopherol.
47. The vegetable oil composition of claim 40 wherein
the tocopherol is at least two of alpha, beta and delta
tocopherol.
48. A method for stabilizing an oil useful in deep fry-
ing comprising adding to a triglyceride wherein at least
about 70% of the fatty acid moieties in the triglyceride are
oleic; less than about 20% of the fatty acid moieties in the
triglyceride are linoleic, and further comprising about 100
to about 3,500 ppm of a tocopherol based on the weight of the
triglyceride.
49. The method of claim 48 wherein the oil is used in
deep frying.
50. The method of claim 48 wherein the AOM of the oil
is at least 100 hours.
51. The method of claim 48 wherein the AOM of the oil
is at least 150 hours.
52. An edible oil composition comprising an oleic acid
content of at least 70% of the fatty acid moieties and to-
copherol wherein the AOM of the composition is at least 100.
53. The oil composition of claim 52 wherein the oleic
acid content is at least 78% and the AOM is at least 150.

Description

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


``` 2122907

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DXt. 2535R 02/12/~
VEGETABLE OIL COMPOSITIONS
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BACKGROUND ~F THE INVENTION
1. Field of the Invention
The present invention relates to vegetable oil composi-
tions and in particular to those vegetable oil compositions
which are edible.
2. Introduction to the Invention
The present invention deals with a manner of stabilizing
vegetable oils against oxidation. The invention in particu-
larly deals with high oleic oils which are believed to be
more healthy for the diet. In particular, high oleic content
vegetable oils are believed to reduce low density lipoprotein
cholesterol. Low density lipoprotein cholesterol has been
referred in the literature as "bad cholesterol" which is that
believed responsible for plaque buildup on the walls of blood
vessels.
The use of high oleic vegetable oils has been of further
interest in the diet in recent years in that it is also be-
lieved that a high saturated fat content in the diet may also
lead to the formation of plaque. Thus the present invention
provides a benefit in giving an oxidatively stable oil in
which two distinct mechanisms are believed to reduce choles-
terol.
It is noted that saturated fats are more stable than
unsaturated fats because of the àbsence of a double bond in
saturated fats. Of course, as the oils of the present inven-
tion are high in oleic content they correspondingly contain a
high degree of mono-unsaturation in the oil.
The higher the degree of unsaturation in an oil the more

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likely that the oil will go rancid ~oxidize). It is particu-
larly critical in dietary oils which are used for frying,
3 such as French frying, that the oil be stable for a long pe-
riod of time. Many fast food manufacturers have utilized
saturated fats, and in particular saturated animal fats, be-
cause of their ability to withstand long periods of time at
elevated temperatures in the manufacture of fried foods. of
course, as the fried food absorbs the saturated fat such is
taken into the human diet. Thus while a saturated fat may be
oxidatively stable for frying it is unfortunate that a di-
etary component with the problems previously addressed are
encountered.
Many antioxidants present problems especially when used
at high levels in industrial applications. The tocopherol
antioxidants are environmentally friendly and compliment the
natural oils described herein.
Thus it remains to develop a vegetable oil which is high
in oleic acid content, and low in saturates or polyunsaturat-
ed oils which is oxidatively stable and which may be utilized
for deep frying. Other uses of oils include crankcase, gear
lubricants, transmission oils, tractor oils and hydraulic
fluids.
It is known from United States Patent 2,267,224 issued
December 23, 1941 to Taylor et al that lard shortening may be
stabilized through the use of tocopherol at levels of 0.02%
to 0.06%. The present invention does not deal with lard
which contains large amounts of cholesterol (which should be
avoided in the diet), and the oil of the invention does not
contain the hlgh degree of saturates or linoleic acid moi-
eties which are found in lard. It is further noted that the
compositions of Taylor et al are suggested for use in hydro-
genated lard. In fact it is noted that the tocopherol is
also hydrogenated in Taylor et al.
~ickman in United States Patent 2,349,277 issued May 23,
1944 suggests a method of preparing a deodorized relatively
stable edible triglyceride. Jacobsen in United States Patent
2,363,672 issued November 7, 1941 suggests that animal and



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~ ~122~
- 3 -

vegetable shortenings may be treated by adding a tocopherol-
containing deodorizer sludge to ~hortening and hydrogenating
the resultant mixture.
United States Patent 2,440,606 issued April 27, 1948 to
Hickman suggests methods for obtaining tocopherol or vitamin
E produced during the vacu~m-inert gas deodorization
treatment of vegetable or animal oils. Mattill et al in
United States Patent 2,333,655 issued November 9, 1943 de-
scribes obtaining the use of beta-tocopherol in lard. Simi-
lar disclosures are also found in United States Patent
2,333,656 and 2,333,657 both issued to Mattill et al on No-
vember 9, 1943.
Golub in United States Patent 3,117,866 issued January
14, 1964 discusses the use of phosphatides, oils, and
tocopherol at levels of 0.25% to 2% in an oleaginous composi-
tion. Klaui et al in United States Patent 3,637,772 issued
January 25, 1972 suggests the use of tocopherols in combina-
tion with colamine or its salt, and a higher fatty acid ester
of ascorbic acid. Nelan in United States Patent 3,173,927
issued March 16, 1975 discusses various methods for obtaining
tocopherol.
High oleic vegetable oils with which the present is con-
cerned may be obtained from any one of several sources. The
first and most important source of high oleic acid content
vegetable oils are described in Fick's United States Patents
4,6271192 and 4,743,402 issued respectively December 9, 1986
and May 10, 1988. The Fick patents describe obtaining in
large quantities high oleic vegetable oils having greater
than 80% oleic acid. The Fick oils are also noted for their
high degree of stability with regard to the AOM values as
hereinafter described.
It is also known from European Patent Application 88
312397.8 filed December 29, 1988 that high oleic content
rapeseed (canola) may be used as a source of a high oleic
content vegetable oil. ~ow saturated fat content oils are
described in United States Patent 4,948,811 issued August 14,
1990 to Spinner et al.

-~" 2~22 ~
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The vegetable oil products oE the present invention pro-
vide highly stahle oils for cooking which have the desirable
benefits of low saturate and low linoleic acid levels while
maintaining a relatively high degree of mono-unsaturate in
the oil.
To the extent that any of the foregoing references are
applicable they are herein explicitly incorporated by refer-
ence. Temperatures and pressures given herein are in degrees
C and KPa absolute unless otherwise indicated. When discuss-
ing the fatty acid content of a triglyceride oil such relates
to the average molar amount of the fatty acid species which
make up the triglyceride. Ranges and ratios given herein may
be combined.

_ 5 _ ~ 2


SUMMARY OF THE INVENTION
The present invention describes a natural vegetable oil
composition comprising triglycerides wherein at least about
70% of the fatty acid moieties in the triglyceride are oleic;
less than about 20% of the fatty acid moieties in the tri-
glyceride are linoleic, and further comprising at least about
100 ppm of a tocopherol based on the weight of the triglyc-
eride.
A further embodiment of the present invention is a tri-
glyceride composition wherein at least about 83% of the fatty
acid moieties in the triglyceride are oleic and further in-
cluding in said composition about 500 to about 3,000 ppm of
tocopherol per part of triglycerida.
Yet a further embodiment of the present invention is a
vegetable composition comprising triglycerides wherein at
least about 70% of the fatty acid moieties in the triglycer-
ide are oleic; less than about 20% of the fatty acid moieties
in the triglyceride are linoleic, and further comprising an
antioxidant effective amount of a tocopherol.
A still further useful composition herein is a triglyc-
eride composition wherein at least about 83% of the fatty
acid moieties in the triglyceride are oleic and further in-
cluding in said composition about 500 to about 3,000 ppm of
tocopherol per part of triglyceride.
The present invention also involves a method for stabi-
lizing an oil utilized in deep frying comprising adding to a
triglyceride wherein at least about 70% of the fatty acid
moieties in the triglyceride are olaic; less than about 20%
of the fatty acid moieties in the triglyceride are linoleic,
and further comprising about 100 to about 3,500 ppm of a to-
copherol based on the weight of the triglyceride.
The invention also describes an edible oil composition
comprising an oleic acid content of at least 70% of the fatty
acid moieties and tocopherol wherein the AOM of the composi-
tion is at least 100.

~l 2~J~


DETAILED_DESCRIPTION OF THE_ NVENTION
When discussing an oil herein the chemical make-up of
the oil is a triglyceride, e.g. three moles of a fatty acid
esterifying one mole of glycerine. Thus when discussing the
acid content of the oil it is this portion of the triglycer-
ide which is discussed not the free acid or other esters con-
taining the acid species. A natural oil as described herein
is a non-hydrogenated oil obtained from-plants.
The first aspect to be discussed in the present inven-
tion is the vegetable oil. It is first noted that Fick Unit-
ed States Patent 4,627,192 and 4,743,402 discuss obtaining
high oleic content sunflower oils. The sunflower oils useful
herein typically contain an oleic acid content of greater
than 70% of the fatty acid moieties on average in the oil.
Stated other~ise, each of the three fatty acids that make up
the triglyceride are on average at least 70% oleic.
` Preferably, the oleic acid content of the triglyceride
is greater than 78%, most preferably greater than 80%, yet
more preferably greater than 85% and most preferably greater
than 87%.
The remainder of the fatty acid composition in the tri-
glycerides is typically less than 10% linoleic acid, most
preferably less than 5%, and more preferably less than 3% by
weight linoleic. Most preferably the linoleic content is
less than 2% or 1%. Similarly, other higher unsaturated
acids such as linolenic are also present in substantially
lower amounts than the linoleic acid content~
The saturated fatty acid content of the oil is typically
less than 15%, typically less than 10%, preferably less than
7%, and most preferably less than 3% by weight.
It is also preferred that the oils utilized herein con-
tain at least 85% of the fatty acid species as C18, prefera-
bly 90% and most 92% by weight of 18 carbon species. It is
noted that the total number of carbon atoms carboxylic acid
portion of the oil is included in the foregoing definition.
The oils which may be utilized with the present inven-
tion as previously noted include sunflower, rape or canola as


described in published European Patent 88 312397.8. In fact
any vegetable oil may be utilized including peanut, soya,
corn, safflower, cottonseed, and the like. If desired, tri-
olein might also be utilized as the source of an oil in the
present invention. Triolein is a manufactured oil in which
the oleic acid content of triglyc~eride is 100%.
The second component in the present invention is the
tocopherol component. Various tocopharols are known in the
present in~ention. Tocopherols are a member of the family of
chroman compounds. The various tocopherols which are known
and described in the Merck Index 8th edition include alpha,
beta, delta or gamma tocopherol. Numerous of the references
previously cited herein show commercially available sources
of natural occurring tocopherol.
It is also possible in the present invention to use syn-
thetic tocopherol compounds. The synthetic tocopherol com-
pounds are typically obtained by alkylating the ring struc-
ture to synthetically form a chroman compound. The primary
difference between synthetic and natural tocopherols is that
natural tocopherols have a substantial degree of optical ro-
tation. The synthetic tocopherols due to their formation are
optically balanced in both the dextro and levo forms. Thus
the synthetic tocopherols do not exhibit optical rotation.
There is some difference in the biological activity of
the various tocopherols and as well of natural tocopherols
over synthetic tocopherols. However, for the present inven-
tion the differences in biological activity are not control-
ling in the choice of which tocopherol to utilize as an
antioxidant in the claimed compositions.
The amount of the tocopherol utilized in the present
invention is typically from about 100 to 3,500 ppm of
tocopherol based on the weight of the triglyceride. A pre-
ferred range for the use of the tocopherol in the present
invention is at from 300 to 2,500 ppm. A more preferable
range for the use of the tocopherol in the present invention
is from 500 to 2,000 ppm.
It is preferred that the triglyceride herein not be

~ 1 2 ~ t~
i




hydrogenated, and accordingly, that the oil not have any
trans unsaturation in the oil.
It is further noted herein that the tocopherol may be
utilized in its free orm or as an acceptable salt or ester.
Typically, when the tocopherol is utilized as a salt it is
present as an ester such as the acetate or succinate form.
The use of the salts of tocopherol are typically for the con-
venience o~ the manufacturer of the tocopherol. The amount
of tocopherol utilized herein is specified as the free-form
of the tocopherol.
The tocopherol may be also utilized as various mixtures
of alpha, beta and delta tocopherol. A further variation of
the present invention is the use of the tocopherol in a mix-
ture of the alpha and gamma forms. It is further suggested
herein that the tocopherol not be hydrogenated.
The oils of the present invention enjoy AOM's (active
oxygen method) of greater than 50 hours, preferably greater
than 60 hours, most preferably greater than 70 hours. The
following table may be utilized to show the relationship of
AOM, tocopherol content of a triglyceride mixture and the
oleic acid content of the oil. The AOM is determined by AOCS
procedure CD 12-57.
DESCRIPTION OF THE DRAWINGS
Figure 1 shows the percentage of oleic acid in a vege
table oil on the x-axis and percent increase in AOM after
using tocopherol at 2,000 ppm of the oil. Figure 2 shows the
actual AOM versus the oleic content. Figure 4 shows the raw
data used to obtain Figures 1 and 2.
Figure 3 shows 2 different types of tocopherol in an
oil having an 80% oleic acid content of the triglyceride at
varying tocopherol content. Figure 5 shows the raw data for
Figure 3.

~ ..

I
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ExamPle I
The general method for obtaining the tocopherol treated
oil is to stir the liquid oil and to add the tocopherol in
the appropriate amount. The oil and tocopherol mixture are
agitated. Generally, the oil is at 20~C when mixing is
accomplished.
The total mixing time depends on the respective volumes
and the method o~ addition with, generally, 10 minutes to 1
hour sufficient to disperse the tocopherol in the oil.




~a.~ Y ;~

Representative Drawing

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Administrative Status

For a clearer understanding of the status of the application/patent presented on this page, the site Disclaimer , as well as the definitions for Patent , Administrative Status , Maintenance Fee  and Payment History  should be consulted.

Administrative Status

Title Date
Forecasted Issue Date Unavailable
(86) PCT Filing Date 1992-03-09
(87) PCT Publication Date 1993-09-16
(85) National Entry 1994-05-04
Examination Requested 1997-06-19
Dead Application 2000-03-09

Abandonment History

Abandonment Date Reason Reinstatement Date
1999-03-09 FAILURE TO PAY APPLICATION MAINTENANCE FEE

Payment History

Fee Type Anniversary Year Due Date Amount Paid Paid Date
Application Fee $0.00 1994-05-04
Maintenance Fee - Application - New Act 2 1994-03-09 $100.00 1994-05-04
Registration of a document - section 124 $0.00 1994-10-25
Maintenance Fee - Application - New Act 3 1995-03-09 $100.00 1995-02-16
Maintenance Fee - Application - New Act 4 1996-03-11 $100.00 1996-02-28
Maintenance Fee - Application - New Act 5 1997-03-10 $150.00 1997-03-07
Registration of a document - section 124 $0.00 1997-03-13
Request for Examination $400.00 1997-06-19
Maintenance Fee - Application - New Act 6 1998-03-09 $150.00 1998-03-09
Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
AC HUMKO CORP.
Past Owners on Record
CARRICK, VIRGINIA
THE LUBRIZOL CORPORATION
YODICE, RICHARD
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) 
Cover Page 1995-08-26 1 97
Abstract 1995-08-26 1 70
Claims 1995-08-26 4 349
Drawings 1995-08-26 5 312
Description 1995-08-26 9 713
Assignment 1994-05-04 18 689
PCT 1994-05-04 26 830
Prosecution-Amendment 1997-06-19 1 39
Correspondence 1997-04-08 5 145
Fees 1998-03-09 1 33
Fees 1994-07-13 2 75
Fees 1997-03-07 1 23
Fees 1996-02-28 1 26
Fees 1995-02-16 1 28
Fees 1994-05-04 1 54