CA2111104C - Process and composition for making a uniform liquid, pourable shortening containing high emulsifier levels - Google Patents
Process and composition for making a uniform liquid, pourable shortening containing high emulsifier levelsInfo
- Publication number
- CA2111104C CA2111104C CA 2111104 CA2111104A CA2111104C CA 2111104 C CA2111104 C CA 2111104C CA 2111104 CA2111104 CA 2111104 CA 2111104 A CA2111104 A CA 2111104A CA 2111104 C CA2111104 C CA 2111104C
- Authority
- CA
- Canada
- Prior art keywords
- oil
- process according
- emulsifier
- monoglyceride
- melted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
- A23D9/013—Other fatty acid esters, e.g. phosphatides
Abstract
A process and composition for making a uniform liquid, pourable shortening involves preparing a melted base oil containing partially hydrogenated oil and optionally highly hydrogenated oil, then blending a melted emulsifier containing at least 30 % monoglyceride with the base oil so that the monoglyceride content of the total blend is 10 % is 16 %. The amounts of emulsifier and highly hydrogenated oil are chosen so that they fall within the cross-hatched area ABCD. The melted blend is rapidly cooled and partially crystallized in a first zone, and then worked by agitation in a second zone. The product shortening has the following solid fat index: 3-12 at 50 .degree.F, 0-7 at 70 .degree.F, 0-4 at 80 .degree.F, 0-3 at 92 .degree.F, and not more than 3 at 104 .degree.F.
Description
WO~2~2221~ 2 ~ PCr/US92/04358 . .
PROCESS AND COMPOSITION FOR MAKING A UNIFORM LIQUID, POURABLE SHORTENING CONTAINING HIGH EMULSIFIER LEVELS
Technical Field The present invention relates to a process and composition for making liquid shortenings, in particular for making uniform liquid9 pourable shortenings that contain high levels of emulsifier.
Backqround of the Invention Conventional liquid or "fluid" shortenings contain about 10%
or less emulsifier by weight of the shortening. Liquid shortenings to which very high levels of emulsifier are added have not been made.~ :
It has now been unexpectedly discovered that liquid shortenings containing~high levels of mono-diglyceride emulsifier (in the range of 20~/o tO 32% emulsifier by weight of the shorte~ing) are:particularly suited for making an improYed pizza dough. The dough is~more s~orage stable, han~les better, an~
::: : :
provides~a bet~er baked texture. ~:
:Unfortuna~ly,~there~are several~problems associated with adding ~hese high:emul~sifier levels to a liquid shorteningO We : have found that if the~shortening is made incorrec~ly, it is not pourabl~:, not unifo~rm,~and does~not:provide~the pizza dough improvement;benefits.;:~
~: ~Therefore, it~is an~object of the present invention to : provide:a particular:ltquid shortening composition that contains : high~emulsifier levels and is pourable, uniform, and makes an proved pizza dough~
It :is also an object of the present invention to provide a par~leular process which, when combined with the composition, produces the de ired liquid shortening.
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~;IJ~ o ~ I alTE SHEET
W o 92/22216 PCT/US92/04358 ~
PROCESS AND COMPOSITION FOR MAKING A UNIFORM LIQUID, POURABLE SHORTENING CONTAINING HIGH EMULSIFIER LEVELS
Technical Field The present invention relates to a process and composition for making liquid shortenings, in particular for making uniform liquid9 pourable shortenings that contain high levels of emulsifier.
Backqround of the Invention Conventional liquid or "fluid" shortenings contain about 10%
or less emulsifier by weight of the shortening. Liquid shortenings to which very high levels of emulsifier are added have not been made.~ :
It has now been unexpectedly discovered that liquid shortenings containing~high levels of mono-diglyceride emulsifier (in the range of 20~/o tO 32% emulsifier by weight of the shorte~ing) are:particularly suited for making an improYed pizza dough. The dough is~more s~orage stable, han~les better, an~
::: : :
provides~a bet~er baked texture. ~:
:Unfortuna~ly,~there~are several~problems associated with adding ~hese high:emul~sifier levels to a liquid shorteningO We : have found that if the~shortening is made incorrec~ly, it is not pourabl~:, not unifo~rm,~and does~not:provide~the pizza dough improvement;benefits.;:~
~: ~Therefore, it~is an~object of the present invention to : provide:a particular:ltquid shortening composition that contains : high~emulsifier levels and is pourable, uniform, and makes an proved pizza dough~
It :is also an object of the present invention to provide a par~leular process which, when combined with the composition, produces the de ired liquid shortening.
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~;IJ~ o ~ I alTE SHEET
W o 92/22216 PCT/US92/04358 ~
2 1 1 ~ ~ O 1 2 These and other objects of the inven~ion will be more fully described herein.
All percentages used herein are by weight unless otherwise defined.
Summary of the Invention A process and composition for making a uniform liquid, pourable shortening involves preparing a melted base oil containing partially hydrogenated oil and optionally highly hydrogenated oil, then blending a melted emulsifier containing at leas~ 30% monoglyceride with the base oil so that the monoglyceride content of the total blend is 10% to 16%. The amounts of emulsifier and highly hydrogenated oil are chosen so that they fall within the çross-hatched area ABCD in FIGURE 1.
The melted blend is rapidly eooled and partially crystallized in a first zone, and then worked by agitation in a second zone. The product shortening has the following solid fat index: 3-12 at 50-F, 0-7 at 70~F, 0-4 at 80~F, 0-3 at 92-F, and not more than 3 at 104-F.
:~ 8rief DescriPtion of the Drawin~
In FIGURE l, the cross-hatched area ABCD covers the ~ombinations of~monaglyceride and highly hydrogenated oil that are acseptable to make~a shortening according to the present invention. By "area~A8CD" is meant the area bordered by lines AB, BC, CD and DA between points A, B, C and D. The double cross-hatched area:;EFGHI covers the most preferred combinations of monoglyceride and~highly hydrogenated oil.
Detailed DescriDtion of the Invention Th1s inventl~on 1 S; ~a:process and composition for making a : unifor~ liquid,-pourable shortening Gontaining high leYels of emulsifier. The shortening product is convenient to use because.
it is easily pourable and~pumpable. Further, the shortening is very uni~orm, having: substantially the same composition from batch t~ bat~h and within a~batch. :It has been discovered that the shortening is particularly suited for making an excellent quality ~pizza dough. The shortening is easily blended with the pizza :~ SUBSTITUTE SHEE7-W O 92/22216 3 2 ~
dough components such as flour, salt, water and yeast. Moreover, the shortening yields a longer lasting pizza dough, provides dough handling benefits, and provides an overall higher quality baked pizza dough. (The pizza dough per se is not claimed as part of the present invention.) The process for making the shortening of the invention co~prises:
(a~ preparing a melted base oil comprising between about 96% and 100% melted partially hydrogenated edible oil having an iodine value between about 90 and about 133, and between 0%
and about 4% melted highly hydrogenated edible oil having an iodine value of not more than about 8; then (b) blending a melted emulsifier containing at least about 30%
monoglyceride with the melted base oil in proportions so that the monoglyceride content of the total blend is between about 10% and about 16%;
~ ~c) wherein the amounts of emulsifier and highly hydrogenated oil :~ are chosen so that a plot of percent:monoglyceride versus percent highly hydrogenated oil falls within the ~: cross-ha~ched area ABCD in FI6URE 1;:then : (d) i:n a:first zone,:rapidly cooling the~melted total blend to a temperature between:about 60-F and about 80~F to partially :: ; crystallize the blend; and then (e) -in a second:zone~ working by agitation the partially ; : crystalliz:ed éotal ~blend to further p~omote the formation of : many small~crystals and a 1iquid pourable shnrtening;
: wherein~the pradu:ct shortening has a solid fat index between about 3 and~about 12 at:S0-F,~between 0 and about 7 at 70-F, between 0 and about 4 at 80-F, between 0 and-about 3 at 92-F, and not more than about 3 at 104-F.
~Com~osition: .
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The partially hydrngenated edible~oil and the highly hydrogenated edible oii-c:an be derived from animal, vegetable or marine sources. Preferred partially hydrogenated oils include :
: : : : :
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WO 92/222 1 6 2 1 1 ~ 1 ~ 1 4 Pcr/ usg ~A, . _ . .
soybean oil, corn oil, cottonseed oil, canola oil, sunflower oil, and mixtures thereof.. Soybean oil is most preferred for use as both the partially hydrogenated oil and the highly hydrogenated oil. The partially hydrogenated oil has an iodine value between about 90 and about 133, preferably between about 98 and about 120, more preferably between about 100 and 115, and most preferably about 107. The highly hydrogenated oil (whieh is commonly called a "hardstock") has an iodine value of not more than about 8, and preferably an iodine value of about 8. Iodine value is measured by the standard Wijs Method, which is A.O.C.S. Official Method Cd 1-25 (1989).
The melted base oil comprises a blend of between about 96%
and 100% melted partially hydrogenated oil and between 0~~0 and about 4% melted highly hydrogenated oil. Mixtures of different partially hydrogenated oils and highly hydrogenated oils can be used to make up these percentages. Preferably the base oil comprises between:about 97.5% and 100% partially hydrogenated oil and between 0% and about 2.5% highly hydrogenated oil, and most preferably 100%~partially hydrogenated oil and 0% highly hydrogenated oil.
A melted emulsifi~er (or mixtures of emulsifiers) containing at least about.30%~monoglyceride is blended with the base oil in proportions so that~the:monoglyceride content of the total blend (the partially hydrogen'ated oil plus any highly hydrogenated oil plus-the emulsifier)~ is betwe~en a~out 10% and about 16%, preferably-between~:;about 12% and about 14%, and most preferably about.13X.~
: A preferred:emulslfl~er is a mono-diglyceride containing between abou$ 30X~and about 70% monoglyceride. More preferably th~ emulsi~ier is a mono-diglyceride containing be~ween about 4q%
and about 60% monoglyceride, between about 32% and about 52%.
diglyceride an~;not;:more than about 16% triglyeeride, and most preferably about 50% monoglyceride, ~bout 42% diglyceride and about 8% triglycer:ide~ When such a mono-diglyceride emulsifier is used, the total blend (partially hydrogenated oil plus any highly ~ :
SUBS~ JTE SHEET
W o 92J22216 ~ O ~ pcT/us~2/o43s8 hydrogena~ed oil plus emulsifier3 preferably contains bet~een about 68% and about 80% base oil (partially hydrogenated oil plus any highly hydrogenated oil) and between about 20% and about 32%
emulsifier. More preferably the total blend contains between about 72% and about 76% base oil and between about 24% and about 28% emulsifier, and most preferably about 74% base oil and about 26% emulsifier. These high levels of emulsifier are in contrast to the levels of about 10% or less found in conventional liquid shortenings.
Emulsifiers prepared from a soft base oil (not from a hardstock) are preferred for use in the present invention because they provide the most desired solid fat index in the shortening product. ~he iodine value of the emulsifier is preferably between about 60 and about 85, and more preferably between about 70 and about 75. A mono-diglyceride emulsifier containing about 50%
monoglyceride, about 42% diglyceride, and about 8% triglyceride, and having an iodine value between iO and 75, can be purchased :
from ~an Den Bergh Co., Lisle, Illinois 60532. Many other similar emulsifiers are commerciall~y available.
It has been discovered that in order to have a shortening that is both poura~le~at ambient temperature and provides the optimum dough improvement benefits, the amount of highly hyd~genated oil added to the base oil must be balanced against the amount of monog1yoeride in the total blend. FIGURE 1 shows a graph of "Percent Monoglyceride in Total Blend" versus "Percent Highly Hydrogenated Oil in Base Oil". The cross-hatched area ABCD
covers $he combinati~ons~of monoglyceride and highly hydrogenated ~oil~that are acceptable~to make a shortening that is both pourable and that provides optimum pizza~dough improvements. The double -cross-hatched area EFGHI covers the most preferred co~binations of monoglyceride and highly hydrogenated oil. In the present invention, the amounts~of emulsifier and highly hydrogenated oil are chosen so that a plot of percent monoglyceride versus percent highly hydrogenated oil falls within the acceptable or preferred area~in the FT6URE I graph. The area in the graph below and to :: :
SUE~ I ~ ~ ~ITE SHEEr WO 92/222~6 PC~/VS92/04358 J ~ -6~
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the right of the cross~hatched area covers combinations that make a shortening which is not pourable at ambient temperature. The area in the graph above the cross-hatched area covers combinations that make a shortening which does not provide adeq~ate dough improvements.
The shortening of the invention has a solid fat index between about 3 and about 12 at 50-f, between 0 and about 7 at 70'F, between 0 and about 4 at 80-F, between 0 and about 3 at 92-F, and not more than about 3 at 104-~. The shortening preferably has a solid fat index between about 3 and about 8 at 50-F, between 0 and about 4 at 70-F, between 0 and about 2 at 80-F, between 0 and ~out 2 at 92~F, and not more than about 2 at 104~F. Solid fat index is measured by the Dilatometric Method, which is A.O~C.S.
Official Method Cd 10-57 ~1989). Thé last SFI measurement is done at 104~F instead of 100'F as in the Official Method. Results are expressed in units of mL/kg.
Process:
The method for making the shortenings of the present invention involves preparing a melted base oil by melting and blending partially hydrogenated oil and optionally highly hydrogenated ail, and then melting an emulsifier and blending it with the melted base o;l. This is usually done at temperatures above~110-F, preferably at temperatures of 120-F to 140'F.
The~resulting blend is then rapidly cooled in a first zone to a-temperature betw~en about:60-F and about 80~F~ preferably :between about 65~F~and about 75-F, to partially crystallize the blend.~ ;This temperature: range corresponds to a temperature at or bel~ow the nucleat~ion poiht;of the triglycerides in the shortening.
S~ch cooling can be carried out in a scraped surface heat-exchanger, such as a Votator unit manufactured by Chemtron, Inc.
(commonly known~as an~A:unit in shortening prooessing). This A
unit ~onsists of a steel shaft rotating in a tube. This tube is cooled externally by llquid ammonia, brine, or other refrigerants.
The rotator shaft: is fitted with scraper blades which press against the cool inner surfaoe at high rotation speeds. The high ~:
SU BSTITIJTE SHEET
:
W 0 92J22216 2 I ~ I 1 3 4 PCT/US92/043~8 internal pressures and chilling action induce nucleation and crystallization of the shortenings.
The time for rapid cooling is generally between about 5 seconds and about 30 seconds depending on the type of equipment used, and preferably between about 8 seconds and about 20.seconds when done using a Votator A unit.
Other cooling devices such as shell and tube heat exchangers or thin walled heat exchangers can be used if desired. Other useful scraped surface heat exchangers similar to the Votator A
unit are the Thermutator (Cherry-Burrell, USA), the Perfector (Gerstenberg and Agger, Denmark), and the Kombinator (Shroeder, West Germany~.
Typically the melted oil is precooled before entering the heat exchanger, pre~erably to a temperat~re not far above the nucleation point of the triglycerides. Precooling is more energy ef~icient. The Votator System employs a precooler before the A
unit.
Next, the partially crystallized blend is worked by agitation in a second ~one without additional cooling to further promote the formaticn of many small crysta7s and a liquid pourable shortening.
:~ The blend is worked in what is known in the shortening field as a worki~ng B unit ~as~opposed to a static 8 unit), preferably a : picker unit.: A picker unit typically consists of a large diameter tube havingistator pins in the inner cylinder wall and a rotating ~ ~~ shaft:fitted with rotor pins. The eombination of stator and rotor :~ pins~mechanically works the biend as it passes through the unit.
Other~designs such as~a rotating shaft with rotor pins but a :cylinde~r wi~thout stator pins can also be used. The rotor rotates at speeds of from about 50 to about 1000 rpm. The working B unit p~omotes triglyceride crystal growth within the shortening while working the shortentng to form uniform crystal sizes. During the ~process the heat of crystallization and the work added usually cause a temperature increase of 10~-15DF. This working period requires at least about 1 ~inute, preferably at least about 1.5 :- :
SU~ ~ JTE: SHEET
W o 92/22216 2 ~ 4 PCT/US92/0435 minutes7 and more preferably at least about 1~8 minutes.
Crystallization approaches completion in the B unit.
Working B units are described in the following references:
Applewhite, BaileY's Industrial Oil and Fat Products, 4th Ed., Vol. 3, p. 78 (1985); Haighton, "Blending, Chilling, and T.empering of Margarines and Shortenings", J. Am. Oil Chemists Soc. Vol. 53 ~June, 1976)7 pp. 397-399; and Wiedermann, I'Margarine and Margarine Oil, Formulation and Control", J. Am. Oil Chemists Soc.
Vol. 55 (December, 1978), pp. 823-829. It is possible that a slowly agitated "tempering tank" rather than a conventi3nal B unit might suffice for the "working by agitation" step of this invention.
The Votator System whieh includes an A unit and a B unit is described in U.S. Patent 3,568,463, and the process of the Votator System is described in U.S. Patent 3,455,700; both patents are incorporated by reference herein. Reference may be made to these patents for a complete descrlption of the system and process.
The step of working by agitation has been found to be crit k al to making a 1iquid pourable shortening according to the preent invention. B units are sometimes but not always used when making conventional liquid shortenings. We have discovered that in making the liquid shortenings of the invention containi ng Yery high emulsifier levels, the~use of a B unit is required to make a shortening ~hich will be~ pourable and not too solid. Agitation is believed to be crltical~for the right crystal particle size distribution and a s1;able, pourable product. Example 2 herein-below describes two~:paral:lel process runs, one with a B unit and the other without a B unit.~ The shortening made without the B
unit firmed up and was not pourable after a time af only about 10 secnnds.
After the B unit, the shortening is then collected in~a st~rage tank or fil~ed~directly into desired containers, usually drums. The shortening can optionally be tempered by holding it in a quiescent state at a controlled temperature (preferably between 70~F and 90~F).
.
SU13~TJl~TE SHEET
WO 92~22216 2 1 1 1 1 0 'I P~US92/04358 . .. g ExarnPl e Example 1, Parts A-C, describes the preparation of a series of shortenings that lead to the discovery of the present eomposition for making a liquid pourable shortening containing high emulsifier levels.
Part A:
A stable, uniform, but non-pourable at ambient tempe~ature shortening is made from the following formula:
ComPonent Weiqht %
1. Soybean oil, refinedj bleached and ) 67.2 hydrogenated to approx. IV 107 j Blend 2. Soybean oil, refined, bleached and ) deodorized 2.8 hydrogenated to approx. IV 8 ~hardstock) J
3. Emulsifier~(mono- and diglycerides, 30.0 ~: containing 50% monoglyceride) oo.ax The soybean:oil components~and emulsifier are melted and : blended together at~about~l29-F. This blend is pumped : continuously through~a scraped surface:heat exchanger (freezer) at :a~rate~of 406.~pounds/haur.~ The freezer outlet temperature is 7~-F.~ The~product then enters~a picker:box, where~.the heat of crystall~zation~causes:the product temperature to:rise to 81~F.
Next,~the~product~enters a~scraped surface~heat exchanger where the~prod~ct:temperature:is::raised to 95'F, and then held in a slowly:agitated tempering:tank for one hour before filling product ~ :into sample jars:.~
:~ The shortening p.roduct contains 15~O.monoglyceride in the total blend, and 4% highly hydrogenated oil as a percentage of the base oil. Samples~held~at::70-F overnight~firm up and are not :: pourable.~ Product:held at 90-F overnight remains fluid but firms up~upon return to:~ambient (room) temperature. This product does ~ ~:
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SU8& 1 ~ I aJTE S~EET
WO 92/22216 . P~tl~JS92/0435~
o-not meet the requirements of a uniform, pourable liquid shortening at ambient temperatures.
Part B:
The following formula is prepared.
.
Component Weiqht %
1. Soybean oil, refined~ bleached and ) 68.32 hydrogenated to approx. IV 107 ) Blend 2. Soybean oil, refined, bleached and ) deodorized 1.68 hydrogenated to approx. IY 8 (hardstock) 3. Emulsifier (mono- and diglycerides, 30.00 containing 50% monoglyceride) 100 . 0~%
The melted and blendcd formulation is processed in the same manner and under essentially the same conditions as described in Part A. The shor~ening contains 15% monoglyceride in the total blend, and 2.4% highly hydrogenated oil as a percentage of the base oil. The physical properties (pourability) are similar to those in Part A and are judged not quite acceptable.
Part C:
The product from Part B is melted and diluted with melted soybean oil I~ 107 in the following manner to achieve lower levels of monoglyceride and highly hydrogenated oil.
Comwnent Weiqht %
1. Shortening from Part B - 80.0 2. Soybean oil, refined, bleached, hydrogenated to approx. IV 107, and deodorized 20.0 1~.0%
The melted and blended fsrmulation is processed in the same manner and under essentially the same conditions as described in Part A. The shortening product contains 12% monoglyceride in the SllJ135rlTUTE SHEET
21:1 1 I 0~
WO g2/2~216 PCI~/US92/04358 total blend, and 1.8% highly hydrogenated oil as a percentage of the base oil. The product is uniform, stable, and pourable at amblent temperature. The product is functional in the intended pizza dough application and thus satisfies all of the desired qualities of this product.
Example 2 This example describes the best mode of the present invention, a successful commercial or plant-size production run.
An unsuccessful production run is also described which illustrates the necessity of using a~3 unit in the process of the present invention. The following composition is formulated.
ComDonent Weiqht. lbs. Weiqht %
1. Soybean oil, refined, 44,798 73.68 bleached, hydrogenated to approx. IY 107, and deodorized 2. Emulsifier (mono- and ~' 16,000 26.32 diglycerides,~ containing 49.4Z monoglycerides) 100 . 00%
The~soybean oi1~ and emulsifier are melted and blended together~at~a temperature between 130~F and 140-F. The melted and blended;formulati~on~i;s lnitially processed continuously through two parallel Votato'r Systems~see U.S. Patent 3,568,463), each at a nominal~rate~of lO,OOO~ bs/hour. The melted blend at 130-F to 140-F is pumped through a precooler where it is cooled to about 115-F and then spl'it 1nto two parallel streams. In one stream, the product flows throu,gh a scraped surface heat exchanger (Votator A unit) where it is rapidly chilled to about 73-F over a time of about 9-1/2 seconds. The product continues to flow through a Votator~B~unit where it is worked by igitation for about 1.9 minutes, and the temperature rises to between about ~0--84-F.
The shortening then flows into a storage tank. The second stream ~: :
, :~
:' :
~ SU~SIITUTE SH~1 w~g2~222l6 2~ 0 1 -12- PCT/U~g2/04358 also flows through a Votator A unit and is chilled to about 73-F
over about 9-1/2 seconds. In contrast to the first freezing system, this second freezing syste~ is not proYided with a Votator B unit. It is observed that product leaving the B unit in the first stream is uniform and pourable and remains so, while product sampled from the second system without a B unit is uniform and pourable initially, but after a time of only about 10 seconds the product firms up so that a cup containing the product can be turned upside down and no product will flow out. This lack of pourability is undesirable5 so that it is conc1uded that some degree of agitation during crystallization after rapid cooling in the freezer is required.
Product processed only through the freezing system containing the B unit is collected in a storage tank until the entire batch is processed. The uniform, pourable product is then packed into dru~s. It is belieYed that the product may also be packed directly into containers such as drums without collecting the entire batch in a storage tank. This alternate pack out has been accomplished in later runs.
The measured solid fat index of the liquid pourable shorteqing is approximately 4 at SO-F, 1 at 70-F, 0 at 80-F, 0 at 92~-F,~and 0 at 104-F.
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SVE~ 111 ~JTE 5HEEr
All percentages used herein are by weight unless otherwise defined.
Summary of the Invention A process and composition for making a uniform liquid, pourable shortening involves preparing a melted base oil containing partially hydrogenated oil and optionally highly hydrogenated oil, then blending a melted emulsifier containing at leas~ 30% monoglyceride with the base oil so that the monoglyceride content of the total blend is 10% to 16%. The amounts of emulsifier and highly hydrogenated oil are chosen so that they fall within the çross-hatched area ABCD in FIGURE 1.
The melted blend is rapidly eooled and partially crystallized in a first zone, and then worked by agitation in a second zone. The product shortening has the following solid fat index: 3-12 at 50-F, 0-7 at 70~F, 0-4 at 80~F, 0-3 at 92-F, and not more than 3 at 104-F.
:~ 8rief DescriPtion of the Drawin~
In FIGURE l, the cross-hatched area ABCD covers the ~ombinations of~monaglyceride and highly hydrogenated oil that are acseptable to make~a shortening according to the present invention. By "area~A8CD" is meant the area bordered by lines AB, BC, CD and DA between points A, B, C and D. The double cross-hatched area:;EFGHI covers the most preferred combinations of monoglyceride and~highly hydrogenated oil.
Detailed DescriDtion of the Invention Th1s inventl~on 1 S; ~a:process and composition for making a : unifor~ liquid,-pourable shortening Gontaining high leYels of emulsifier. The shortening product is convenient to use because.
it is easily pourable and~pumpable. Further, the shortening is very uni~orm, having: substantially the same composition from batch t~ bat~h and within a~batch. :It has been discovered that the shortening is particularly suited for making an excellent quality ~pizza dough. The shortening is easily blended with the pizza :~ SUBSTITUTE SHEE7-W O 92/22216 3 2 ~
dough components such as flour, salt, water and yeast. Moreover, the shortening yields a longer lasting pizza dough, provides dough handling benefits, and provides an overall higher quality baked pizza dough. (The pizza dough per se is not claimed as part of the present invention.) The process for making the shortening of the invention co~prises:
(a~ preparing a melted base oil comprising between about 96% and 100% melted partially hydrogenated edible oil having an iodine value between about 90 and about 133, and between 0%
and about 4% melted highly hydrogenated edible oil having an iodine value of not more than about 8; then (b) blending a melted emulsifier containing at least about 30%
monoglyceride with the melted base oil in proportions so that the monoglyceride content of the total blend is between about 10% and about 16%;
~ ~c) wherein the amounts of emulsifier and highly hydrogenated oil :~ are chosen so that a plot of percent:monoglyceride versus percent highly hydrogenated oil falls within the ~: cross-ha~ched area ABCD in FI6URE 1;:then : (d) i:n a:first zone,:rapidly cooling the~melted total blend to a temperature between:about 60-F and about 80~F to partially :: ; crystallize the blend; and then (e) -in a second:zone~ working by agitation the partially ; : crystalliz:ed éotal ~blend to further p~omote the formation of : many small~crystals and a 1iquid pourable shnrtening;
: wherein~the pradu:ct shortening has a solid fat index between about 3 and~about 12 at:S0-F,~between 0 and about 7 at 70-F, between 0 and about 4 at 80-F, between 0 and-about 3 at 92-F, and not more than about 3 at 104-F.
~Com~osition: .
::::
The partially hydrngenated edible~oil and the highly hydrogenated edible oii-c:an be derived from animal, vegetable or marine sources. Preferred partially hydrogenated oils include :
: : : : :
~ :
WO 92/222 1 6 2 1 1 ~ 1 ~ 1 4 Pcr/ usg ~A, . _ . .
soybean oil, corn oil, cottonseed oil, canola oil, sunflower oil, and mixtures thereof.. Soybean oil is most preferred for use as both the partially hydrogenated oil and the highly hydrogenated oil. The partially hydrogenated oil has an iodine value between about 90 and about 133, preferably between about 98 and about 120, more preferably between about 100 and 115, and most preferably about 107. The highly hydrogenated oil (whieh is commonly called a "hardstock") has an iodine value of not more than about 8, and preferably an iodine value of about 8. Iodine value is measured by the standard Wijs Method, which is A.O.C.S. Official Method Cd 1-25 (1989).
The melted base oil comprises a blend of between about 96%
and 100% melted partially hydrogenated oil and between 0~~0 and about 4% melted highly hydrogenated oil. Mixtures of different partially hydrogenated oils and highly hydrogenated oils can be used to make up these percentages. Preferably the base oil comprises between:about 97.5% and 100% partially hydrogenated oil and between 0% and about 2.5% highly hydrogenated oil, and most preferably 100%~partially hydrogenated oil and 0% highly hydrogenated oil.
A melted emulsifi~er (or mixtures of emulsifiers) containing at least about.30%~monoglyceride is blended with the base oil in proportions so that~the:monoglyceride content of the total blend (the partially hydrogen'ated oil plus any highly hydrogenated oil plus-the emulsifier)~ is betwe~en a~out 10% and about 16%, preferably-between~:;about 12% and about 14%, and most preferably about.13X.~
: A preferred:emulslfl~er is a mono-diglyceride containing between abou$ 30X~and about 70% monoglyceride. More preferably th~ emulsi~ier is a mono-diglyceride containing be~ween about 4q%
and about 60% monoglyceride, between about 32% and about 52%.
diglyceride an~;not;:more than about 16% triglyeeride, and most preferably about 50% monoglyceride, ~bout 42% diglyceride and about 8% triglycer:ide~ When such a mono-diglyceride emulsifier is used, the total blend (partially hydrogenated oil plus any highly ~ :
SUBS~ JTE SHEET
W o 92J22216 ~ O ~ pcT/us~2/o43s8 hydrogena~ed oil plus emulsifier3 preferably contains bet~een about 68% and about 80% base oil (partially hydrogenated oil plus any highly hydrogenated oil) and between about 20% and about 32%
emulsifier. More preferably the total blend contains between about 72% and about 76% base oil and between about 24% and about 28% emulsifier, and most preferably about 74% base oil and about 26% emulsifier. These high levels of emulsifier are in contrast to the levels of about 10% or less found in conventional liquid shortenings.
Emulsifiers prepared from a soft base oil (not from a hardstock) are preferred for use in the present invention because they provide the most desired solid fat index in the shortening product. ~he iodine value of the emulsifier is preferably between about 60 and about 85, and more preferably between about 70 and about 75. A mono-diglyceride emulsifier containing about 50%
monoglyceride, about 42% diglyceride, and about 8% triglyceride, and having an iodine value between iO and 75, can be purchased :
from ~an Den Bergh Co., Lisle, Illinois 60532. Many other similar emulsifiers are commerciall~y available.
It has been discovered that in order to have a shortening that is both poura~le~at ambient temperature and provides the optimum dough improvement benefits, the amount of highly hyd~genated oil added to the base oil must be balanced against the amount of monog1yoeride in the total blend. FIGURE 1 shows a graph of "Percent Monoglyceride in Total Blend" versus "Percent Highly Hydrogenated Oil in Base Oil". The cross-hatched area ABCD
covers $he combinati~ons~of monoglyceride and highly hydrogenated ~oil~that are acceptable~to make a shortening that is both pourable and that provides optimum pizza~dough improvements. The double -cross-hatched area EFGHI covers the most preferred co~binations of monoglyceride and highly hydrogenated oil. In the present invention, the amounts~of emulsifier and highly hydrogenated oil are chosen so that a plot of percent monoglyceride versus percent highly hydrogenated oil falls within the acceptable or preferred area~in the FT6URE I graph. The area in the graph below and to :: :
SUE~ I ~ ~ ~ITE SHEEr WO 92/222~6 PC~/VS92/04358 J ~ -6~
. .
the right of the cross~hatched area covers combinations that make a shortening which is not pourable at ambient temperature. The area in the graph above the cross-hatched area covers combinations that make a shortening which does not provide adeq~ate dough improvements.
The shortening of the invention has a solid fat index between about 3 and about 12 at 50-f, between 0 and about 7 at 70'F, between 0 and about 4 at 80-F, between 0 and about 3 at 92-F, and not more than about 3 at 104-~. The shortening preferably has a solid fat index between about 3 and about 8 at 50-F, between 0 and about 4 at 70-F, between 0 and about 2 at 80-F, between 0 and ~out 2 at 92~F, and not more than about 2 at 104~F. Solid fat index is measured by the Dilatometric Method, which is A.O~C.S.
Official Method Cd 10-57 ~1989). Thé last SFI measurement is done at 104~F instead of 100'F as in the Official Method. Results are expressed in units of mL/kg.
Process:
The method for making the shortenings of the present invention involves preparing a melted base oil by melting and blending partially hydrogenated oil and optionally highly hydrogenated ail, and then melting an emulsifier and blending it with the melted base o;l. This is usually done at temperatures above~110-F, preferably at temperatures of 120-F to 140'F.
The~resulting blend is then rapidly cooled in a first zone to a-temperature betw~en about:60-F and about 80~F~ preferably :between about 65~F~and about 75-F, to partially crystallize the blend.~ ;This temperature: range corresponds to a temperature at or bel~ow the nucleat~ion poiht;of the triglycerides in the shortening.
S~ch cooling can be carried out in a scraped surface heat-exchanger, such as a Votator unit manufactured by Chemtron, Inc.
(commonly known~as an~A:unit in shortening prooessing). This A
unit ~onsists of a steel shaft rotating in a tube. This tube is cooled externally by llquid ammonia, brine, or other refrigerants.
The rotator shaft: is fitted with scraper blades which press against the cool inner surfaoe at high rotation speeds. The high ~:
SU BSTITIJTE SHEET
:
W 0 92J22216 2 I ~ I 1 3 4 PCT/US92/043~8 internal pressures and chilling action induce nucleation and crystallization of the shortenings.
The time for rapid cooling is generally between about 5 seconds and about 30 seconds depending on the type of equipment used, and preferably between about 8 seconds and about 20.seconds when done using a Votator A unit.
Other cooling devices such as shell and tube heat exchangers or thin walled heat exchangers can be used if desired. Other useful scraped surface heat exchangers similar to the Votator A
unit are the Thermutator (Cherry-Burrell, USA), the Perfector (Gerstenberg and Agger, Denmark), and the Kombinator (Shroeder, West Germany~.
Typically the melted oil is precooled before entering the heat exchanger, pre~erably to a temperat~re not far above the nucleation point of the triglycerides. Precooling is more energy ef~icient. The Votator System employs a precooler before the A
unit.
Next, the partially crystallized blend is worked by agitation in a second ~one without additional cooling to further promote the formaticn of many small crysta7s and a liquid pourable shortening.
:~ The blend is worked in what is known in the shortening field as a worki~ng B unit ~as~opposed to a static 8 unit), preferably a : picker unit.: A picker unit typically consists of a large diameter tube havingistator pins in the inner cylinder wall and a rotating ~ ~~ shaft:fitted with rotor pins. The eombination of stator and rotor :~ pins~mechanically works the biend as it passes through the unit.
Other~designs such as~a rotating shaft with rotor pins but a :cylinde~r wi~thout stator pins can also be used. The rotor rotates at speeds of from about 50 to about 1000 rpm. The working B unit p~omotes triglyceride crystal growth within the shortening while working the shortentng to form uniform crystal sizes. During the ~process the heat of crystallization and the work added usually cause a temperature increase of 10~-15DF. This working period requires at least about 1 ~inute, preferably at least about 1.5 :- :
SU~ ~ JTE: SHEET
W o 92/22216 2 ~ 4 PCT/US92/0435 minutes7 and more preferably at least about 1~8 minutes.
Crystallization approaches completion in the B unit.
Working B units are described in the following references:
Applewhite, BaileY's Industrial Oil and Fat Products, 4th Ed., Vol. 3, p. 78 (1985); Haighton, "Blending, Chilling, and T.empering of Margarines and Shortenings", J. Am. Oil Chemists Soc. Vol. 53 ~June, 1976)7 pp. 397-399; and Wiedermann, I'Margarine and Margarine Oil, Formulation and Control", J. Am. Oil Chemists Soc.
Vol. 55 (December, 1978), pp. 823-829. It is possible that a slowly agitated "tempering tank" rather than a conventi3nal B unit might suffice for the "working by agitation" step of this invention.
The Votator System whieh includes an A unit and a B unit is described in U.S. Patent 3,568,463, and the process of the Votator System is described in U.S. Patent 3,455,700; both patents are incorporated by reference herein. Reference may be made to these patents for a complete descrlption of the system and process.
The step of working by agitation has been found to be crit k al to making a 1iquid pourable shortening according to the preent invention. B units are sometimes but not always used when making conventional liquid shortenings. We have discovered that in making the liquid shortenings of the invention containi ng Yery high emulsifier levels, the~use of a B unit is required to make a shortening ~hich will be~ pourable and not too solid. Agitation is believed to be crltical~for the right crystal particle size distribution and a s1;able, pourable product. Example 2 herein-below describes two~:paral:lel process runs, one with a B unit and the other without a B unit.~ The shortening made without the B
unit firmed up and was not pourable after a time af only about 10 secnnds.
After the B unit, the shortening is then collected in~a st~rage tank or fil~ed~directly into desired containers, usually drums. The shortening can optionally be tempered by holding it in a quiescent state at a controlled temperature (preferably between 70~F and 90~F).
.
SU13~TJl~TE SHEET
WO 92~22216 2 1 1 1 1 0 'I P~US92/04358 . .. g ExarnPl e Example 1, Parts A-C, describes the preparation of a series of shortenings that lead to the discovery of the present eomposition for making a liquid pourable shortening containing high emulsifier levels.
Part A:
A stable, uniform, but non-pourable at ambient tempe~ature shortening is made from the following formula:
ComPonent Weiqht %
1. Soybean oil, refinedj bleached and ) 67.2 hydrogenated to approx. IV 107 j Blend 2. Soybean oil, refined, bleached and ) deodorized 2.8 hydrogenated to approx. IV 8 ~hardstock) J
3. Emulsifier~(mono- and diglycerides, 30.0 ~: containing 50% monoglyceride) oo.ax The soybean:oil components~and emulsifier are melted and : blended together at~about~l29-F. This blend is pumped : continuously through~a scraped surface:heat exchanger (freezer) at :a~rate~of 406.~pounds/haur.~ The freezer outlet temperature is 7~-F.~ The~product then enters~a picker:box, where~.the heat of crystall~zation~causes:the product temperature to:rise to 81~F.
Next,~the~product~enters a~scraped surface~heat exchanger where the~prod~ct:temperature:is::raised to 95'F, and then held in a slowly:agitated tempering:tank for one hour before filling product ~ :into sample jars:.~
:~ The shortening p.roduct contains 15~O.monoglyceride in the total blend, and 4% highly hydrogenated oil as a percentage of the base oil. Samples~held~at::70-F overnight~firm up and are not :: pourable.~ Product:held at 90-F overnight remains fluid but firms up~upon return to:~ambient (room) temperature. This product does ~ ~:
: :
SU8& 1 ~ I aJTE S~EET
WO 92/22216 . P~tl~JS92/0435~
o-not meet the requirements of a uniform, pourable liquid shortening at ambient temperatures.
Part B:
The following formula is prepared.
.
Component Weiqht %
1. Soybean oil, refined~ bleached and ) 68.32 hydrogenated to approx. IV 107 ) Blend 2. Soybean oil, refined, bleached and ) deodorized 1.68 hydrogenated to approx. IY 8 (hardstock) 3. Emulsifier (mono- and diglycerides, 30.00 containing 50% monoglyceride) 100 . 0~%
The melted and blendcd formulation is processed in the same manner and under essentially the same conditions as described in Part A. The shor~ening contains 15% monoglyceride in the total blend, and 2.4% highly hydrogenated oil as a percentage of the base oil. The physical properties (pourability) are similar to those in Part A and are judged not quite acceptable.
Part C:
The product from Part B is melted and diluted with melted soybean oil I~ 107 in the following manner to achieve lower levels of monoglyceride and highly hydrogenated oil.
Comwnent Weiqht %
1. Shortening from Part B - 80.0 2. Soybean oil, refined, bleached, hydrogenated to approx. IV 107, and deodorized 20.0 1~.0%
The melted and blended fsrmulation is processed in the same manner and under essentially the same conditions as described in Part A. The shortening product contains 12% monoglyceride in the SllJ135rlTUTE SHEET
21:1 1 I 0~
WO g2/2~216 PCI~/US92/04358 total blend, and 1.8% highly hydrogenated oil as a percentage of the base oil. The product is uniform, stable, and pourable at amblent temperature. The product is functional in the intended pizza dough application and thus satisfies all of the desired qualities of this product.
Example 2 This example describes the best mode of the present invention, a successful commercial or plant-size production run.
An unsuccessful production run is also described which illustrates the necessity of using a~3 unit in the process of the present invention. The following composition is formulated.
ComDonent Weiqht. lbs. Weiqht %
1. Soybean oil, refined, 44,798 73.68 bleached, hydrogenated to approx. IY 107, and deodorized 2. Emulsifier (mono- and ~' 16,000 26.32 diglycerides,~ containing 49.4Z monoglycerides) 100 . 00%
The~soybean oi1~ and emulsifier are melted and blended together~at~a temperature between 130~F and 140-F. The melted and blended;formulati~on~i;s lnitially processed continuously through two parallel Votato'r Systems~see U.S. Patent 3,568,463), each at a nominal~rate~of lO,OOO~ bs/hour. The melted blend at 130-F to 140-F is pumped through a precooler where it is cooled to about 115-F and then spl'it 1nto two parallel streams. In one stream, the product flows throu,gh a scraped surface heat exchanger (Votator A unit) where it is rapidly chilled to about 73-F over a time of about 9-1/2 seconds. The product continues to flow through a Votator~B~unit where it is worked by igitation for about 1.9 minutes, and the temperature rises to between about ~0--84-F.
The shortening then flows into a storage tank. The second stream ~: :
, :~
:' :
~ SU~SIITUTE SH~1 w~g2~222l6 2~ 0 1 -12- PCT/U~g2/04358 also flows through a Votator A unit and is chilled to about 73-F
over about 9-1/2 seconds. In contrast to the first freezing system, this second freezing syste~ is not proYided with a Votator B unit. It is observed that product leaving the B unit in the first stream is uniform and pourable and remains so, while product sampled from the second system without a B unit is uniform and pourable initially, but after a time of only about 10 seconds the product firms up so that a cup containing the product can be turned upside down and no product will flow out. This lack of pourability is undesirable5 so that it is conc1uded that some degree of agitation during crystallization after rapid cooling in the freezer is required.
Product processed only through the freezing system containing the B unit is collected in a storage tank until the entire batch is processed. The uniform, pourable product is then packed into dru~s. It is belieYed that the product may also be packed directly into containers such as drums without collecting the entire batch in a storage tank. This alternate pack out has been accomplished in later runs.
The measured solid fat index of the liquid pourable shorteqing is approximately 4 at SO-F, 1 at 70-F, 0 at 80-F, 0 at 92~-F,~and 0 at 104-F.
:~:
' ' ~ , , ~ !
:
::
SVE~ 111 ~JTE 5HEEr
Claims (22)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A process for making a uniform liquid, pourable shortening containing high emulsifier levels comprising:
(a) preparing a melted base oil comprising between about 96% and 100% melted partially hydrogenated edible oil having an iodine value between about 90 and about 133, and between 0%
and about 4% melted highly hydrogenated edible oil having an iodine value of not more than about 8; then (b) blending a melted emulsifier containing at least about 30%
monoglyceride with the melted base oil in proportions so that the monoglyceride content of the total blend is between about 10% and about 16%;
(c) wherein the amounts of emulsifier and highly hydrogenated oil are chosen so that a plot of percent monoglyceride versus percent highly hydrogenated oil falls within the cross-hatched area ABCD in FIGURE 1; then (d) in a first zone, rapidly cooling the melted total blend to a temperature between about 60°F and about 80°F to partially crystallize the blend; and then (e) in a second zone, working by agitation the partially crystallized total blend to further promote the formation of many small crystals and a liquid pourable shortening;
wherein the product shortening has a solid fat index between about 3 and about 12 at 50°F, between 0 and about 7 at 70°F, between 0 and about 4 at 80°F, between 0 and about 3 at 92°F, and not more than about 3 at 104°F.
(a) preparing a melted base oil comprising between about 96% and 100% melted partially hydrogenated edible oil having an iodine value between about 90 and about 133, and between 0%
and about 4% melted highly hydrogenated edible oil having an iodine value of not more than about 8; then (b) blending a melted emulsifier containing at least about 30%
monoglyceride with the melted base oil in proportions so that the monoglyceride content of the total blend is between about 10% and about 16%;
(c) wherein the amounts of emulsifier and highly hydrogenated oil are chosen so that a plot of percent monoglyceride versus percent highly hydrogenated oil falls within the cross-hatched area ABCD in FIGURE 1; then (d) in a first zone, rapidly cooling the melted total blend to a temperature between about 60°F and about 80°F to partially crystallize the blend; and then (e) in a second zone, working by agitation the partially crystallized total blend to further promote the formation of many small crystals and a liquid pourable shortening;
wherein the product shortening has a solid fat index between about 3 and about 12 at 50°F, between 0 and about 7 at 70°F, between 0 and about 4 at 80°F, between 0 and about 3 at 92°F, and not more than about 3 at 104°F.
2. A process according to Claim 1 wherein the amounts of emulsifier and highly hydrogenated oil are chosen so that a plot of percent monoglyceride versus percent highly hydrogenated oil falls within the double cross-hatched area EFGHI in FIGURE 1.
3. A process according to Claim 1 wherein the base oil comprises between about 97.5% and 100% partially hydrogenated oil and between 0% and about 2.5% highly hydrogenated oil.
4. A process according to Claim 3 wherein the base oil comprises 100% partially hydrogenated oil and 0% highly hydrogenated oil.
5. A process according to Claim 1 wherein the iodine value of the partially hydrogenated edible oil is between about 98 and about 120.
6. A process according to Claim 5 wherein the iodine value of the partially hydrogenated edible oil is between about 100 and about 115.
7. A process according to Claim 1 wherein the monoglyceride content of the total blend is between about 12% and about 14%.
8. A process according to Claim 7 wherein the monoglyceride content of the total blend is about 13%.
9. A process according to Claim 1 wherein the emulsifier is a mono-diglyceride containing between about 30% and about 70%
monoglyceride.
monoglyceride.
10. A process according to Claim 9 wherein the emulsifier is a mono-diglyceride containing between about 40% and about 60%
monoglyceride, and between about 32% and about 52% diglyceride.
monoglyceride, and between about 32% and about 52% diglyceride.
11. A process according to claim 10 wherein the emulsifier is a mono-diglyceride containing about 50% monoglyceride, about 42% diglyceride, and about 8% triglyceride.
12. A process according to Claim 11 wherein the total blend contains between about 68% and about 80% base oil and between about 20% and about 32% mono-diglyceride emulsifier.
13. A process according to Claim 12 wherein the total blend contains between about 72% and about 76% base oil and between about 24% and about 28% mono-diglyceride emulsifier.
14. A process according to Claim 1 wherein the emulsifier has an iodine value between about 60 and about 85.
15. A process according to Claim 1 wherein the highly hydrogenated edible oil is soybean oil.
16. A process according to Claim 1 wherein the partially hydrogenated edible oil is selected from the group consisting of soybean oil, corn oil, cottonseed oil, canola oil, sunflower oil, and mixtures thereof.
17. A process according to Claim 16 wherein the partially hydrogenated edible oil is soybean oil.
18. A process according to Claim 1 wherein the product shortening has a solid fat index between about 3 and about 8 at 50°F, between 0 and about 4 at 70°F, between 0 and about 2 at 80°F, between 0 and about 2 at 92°F, and not more than about 2 at 104°F.
19. A process according to Claim 1 wherein the melted blend in step (d) is rapidly cooled to a temperature between about 65°F
and about 75°F.
and about 75°F.
20. A process according to Claim 1 wherein the blend is worked by agitation in step (e) for a time of at least about 1 minute.
21. A process according to Claim 1 wherein the cooling and partial crystallization of step (d) is done in a scraped surface heat exchanger.
22. A process according to Claim 1 wherein the working by agitation in step (e) is done in a picker unit.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US71448291A | 1991-06-13 | 1991-06-13 | |
US714,482 | 1991-06-13 |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2111104A1 CA2111104A1 (en) | 1992-12-23 |
CA2111104C true CA2111104C (en) | 1997-11-25 |
Family
ID=24870225
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA 2111104 Expired - Fee Related CA2111104C (en) | 1991-06-13 | 1992-05-26 | Process and composition for making a uniform liquid, pourable shortening containing high emulsifier levels |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP0590001A1 (en) |
CA (1) | CA2111104C (en) |
MX (1) | MX9202857A (en) |
WO (1) | WO1992022216A1 (en) |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4239786A (en) * | 1979-06-25 | 1980-12-16 | Scm Corporation | Coffee whitener and use of fluid shortening therein |
US4335157A (en) * | 1980-08-05 | 1982-06-15 | Scm Corporation | Fluid shortening |
US4360534A (en) * | 1981-03-02 | 1982-11-23 | The Proctor & Gamble Co. | Method of providing soft flavor chips in aged cookies and composition thereof |
-
1992
- 1992-05-26 WO PCT/US1992/004358 patent/WO1992022216A1/en not_active Application Discontinuation
- 1992-05-26 EP EP92912825A patent/EP0590001A1/en not_active Withdrawn
- 1992-05-26 CA CA 2111104 patent/CA2111104C/en not_active Expired - Fee Related
- 1992-06-12 MX MX9202857A patent/MX9202857A/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
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WO1992022216A1 (en) | 1992-12-23 |
MX9202857A (en) | 1992-12-01 |
CA2111104A1 (en) | 1992-12-23 |
EP0590001A1 (en) | 1994-04-06 |
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