CA1299438C - Method for making better tasting low calorie fat materials - Google Patents
Method for making better tasting low calorie fat materialsInfo
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- CA1299438C CA1299438C CA000530910A CA530910A CA1299438C CA 1299438 C CA1299438 C CA 1299438C CA 000530910 A CA000530910 A CA 000530910A CA 530910 A CA530910 A CA 530910A CA 1299438 C CA1299438 C CA 1299438C
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Abstract
METHOD FOR MAKING
BETTER TASTING LOW CALORIE FAT MATERIALS
Abstract of the Disclosure The present invention is a composition of matter comprising: (a) an edible, non-absorbable, non-digestible low calorie fat material having non-Newtonian pseudoplastic properties at body temperature; and (b) an edible, absorbable, digestible food material which acts as a solvent for the fat material. The rheological properties of the fat material are defined in terms of thixotropy, yield point, thixotropic area, and liquid/solid stability. The composition is useful as a fat substitute in low calorie food products.
The composition provides a non-waxy taste in the mouth, and a laxative side effect is avoided.
BETTER TASTING LOW CALORIE FAT MATERIALS
Abstract of the Disclosure The present invention is a composition of matter comprising: (a) an edible, non-absorbable, non-digestible low calorie fat material having non-Newtonian pseudoplastic properties at body temperature; and (b) an edible, absorbable, digestible food material which acts as a solvent for the fat material. The rheological properties of the fat material are defined in terms of thixotropy, yield point, thixotropic area, and liquid/solid stability. The composition is useful as a fat substitute in low calorie food products.
The composition provides a non-waxy taste in the mouth, and a laxative side effect is avoided.
Description
METHOD FOR MAKINC.
BETTER TASTING LOW CALORIE FAT MATERIALS
Field of the Invention The present invention relates to edible compositions containing certain low calo~e fat materials and additional ingredients to make the materials better tasting in the mouth.
Background of the Invention One of the most common metabolic problems among people today is obesity. This condition is primarily due to ingestion of a greater number of calories than are expended. Fat is the most concentrated form of energy in the diet, with each gram of fat supplying approximately 9 calories. Overa~l, fat constitutes about 40% of the total calories in the diet.
Triglycerides constitute about 90~ of the total fat consumed in the average diet. One method by which the caloric value of edible fat could be lowered would be to decrease the amount of triglyceride that is absorbed in the human system since the usual edible triglyceride fats are almost completely absorbed ( see ~, 2, H . J . Deuel, Interscience Publishers, Inc., New York 1955, page 215). A
low calorie fat offers a convenient and practical method by which obesity can be prevented or overcome.
Low calorie fats which can replace triglycerides are described by Mattson et al. U.S. Patent 3,600,186 to Mattson et al. discloses low calorie, fat-containing, food compositions in which at least a portion of the triglyceride content is replaced with a polyol fatty acid ester, said polyol fatty acid ester havin~ at least four fatty acid ester groups with each fatty acid having rom 8 to 22 carbon atoms.
U . S . Patent 4, 005 ,196 to Jandacek et al. disaloses the low calorie fat-contalning food compositions of the Mattson et al. patent, in combination with sufficient fat-soluble vitamin selected from the group consisting of vitamin A, vitamin D, vitamin E and vitamin K.
The esters disclosed in the Mattson et al. and Jandace et al. patents are effective fat substitutes for use in low calorie food products. Unfortunately, regular ingestion of moderate to high levels of these esters can produce an 5 undesirable "laxative" ef~ect, namely, leakage of the ester through the ~ anal sphincter. One way to prevent this undesirable laxative effect is to formulate the esters so that they are completely solid at body temperature.
Another means of preven~ng the undesirable laxative 10 effect is through the addition to the ester of anti-anal leakage agents such as those described in U.S. Patent 4,005,195 to Jandacek. This patent discloses anti-anal leal~age agents which include solid fatty acids (melting point 37C or higher) and their triglyceride source, and solid polyol fatty acid 15 polyesters. Specifically, the agents are selected from the group consisting of: edible C12 and higher saturated fatty acids, and their edible salts; edible, digestible sources of C12 and higher saturated fatty acids; edible, nonabsorbable, nondigestible solid polyol fatty aeid polyesters having at least
BETTER TASTING LOW CALORIE FAT MATERIALS
Field of the Invention The present invention relates to edible compositions containing certain low calo~e fat materials and additional ingredients to make the materials better tasting in the mouth.
Background of the Invention One of the most common metabolic problems among people today is obesity. This condition is primarily due to ingestion of a greater number of calories than are expended. Fat is the most concentrated form of energy in the diet, with each gram of fat supplying approximately 9 calories. Overa~l, fat constitutes about 40% of the total calories in the diet.
Triglycerides constitute about 90~ of the total fat consumed in the average diet. One method by which the caloric value of edible fat could be lowered would be to decrease the amount of triglyceride that is absorbed in the human system since the usual edible triglyceride fats are almost completely absorbed ( see ~, 2, H . J . Deuel, Interscience Publishers, Inc., New York 1955, page 215). A
low calorie fat offers a convenient and practical method by which obesity can be prevented or overcome.
Low calorie fats which can replace triglycerides are described by Mattson et al. U.S. Patent 3,600,186 to Mattson et al. discloses low calorie, fat-containing, food compositions in which at least a portion of the triglyceride content is replaced with a polyol fatty acid ester, said polyol fatty acid ester havin~ at least four fatty acid ester groups with each fatty acid having rom 8 to 22 carbon atoms.
U . S . Patent 4, 005 ,196 to Jandacek et al. disaloses the low calorie fat-contalning food compositions of the Mattson et al. patent, in combination with sufficient fat-soluble vitamin selected from the group consisting of vitamin A, vitamin D, vitamin E and vitamin K.
The esters disclosed in the Mattson et al. and Jandace et al. patents are effective fat substitutes for use in low calorie food products. Unfortunately, regular ingestion of moderate to high levels of these esters can produce an 5 undesirable "laxative" ef~ect, namely, leakage of the ester through the ~ anal sphincter. One way to prevent this undesirable laxative effect is to formulate the esters so that they are completely solid at body temperature.
Another means of preven~ng the undesirable laxative 10 effect is through the addition to the ester of anti-anal leakage agents such as those described in U.S. Patent 4,005,195 to Jandacek. This patent discloses anti-anal leal~age agents which include solid fatty acids (melting point 37C or higher) and their triglyceride source, and solid polyol fatty acid 15 polyesters. Specifically, the agents are selected from the group consisting of: edible C12 and higher saturated fatty acids, and their edible salts; edible, digestible sources of C12 and higher saturated fatty acids; edible, nonabsorbable, nondigestible solid polyol fatty aeid polyesters having at least
2 0 4 fatty acid ester groups, wherein the polyol is selected from the group consisting of sugars and sugar alcohols containing from 4 to 8 hydroxyl groups and wherein each fatty acid group has from about 8 to about 22 carbon atoms; and edible, nondigestible esters of alpha-branched chain C10-C18 fatty 2 5 acids .
The completely solid esters referred to above, and solid triglycerides or esters used as anti-anal leakage agents, have drawbacks when used in low calorie food compositions. An ester or triglyceride having a high solids content tastes 30 "waxy" in the mouth when ingested. It would be desirable to have a substitute eor triglyceride fats that is still effective at reducing calories, but that does not taste waxy in the mouth.
At the same time, it is critical that this fat substitute not produce an undesired laxative effect.
The completely solid esters referred to above, and solid triglycerides or esters used as anti-anal leakage agents, have drawbacks when used in low calorie food compositions. An ester or triglyceride having a high solids content tastes 30 "waxy" in the mouth when ingested. It would be desirable to have a substitute eor triglyceride fats that is still effective at reducing calories, but that does not taste waxy in the mouth.
At the same time, it is critical that this fat substitute not produce an undesired laxative effect.
3~
It is therefore an cibject oî an aspect of the present invention to provide a cc~T~osition, use~ul as a fat substitute ~n foods, ~ich does not taste wa~y in the m~lth ~en ingested.
It is an object of an aspect s~ this ~vention to provide a 5 c~mposition made with law calorie fat materials, so that food pr~ducts made with the car~osition are l~w in calories.
It is an object of an aspect of the pr~sent invention to avoid a laxative side effect withaut hav~ng to add anti-anal lealcage agents.
mese and c~ther bbjects of the ~vention will be made clear by the disclosure herein.
Summary of the Invention The present invention is a composition of matter having a Solid Fat Content less than about 20% at mouth temperature 15 (92F~ 33.3~C), comprising: (a) an edible, wholly or partia~y nondigestible low calorie fat materisl having, at 100F
(37.8C): (i) a viscosity of at least about 2.5 poise at a shear rate of 800 seconds 1, a viscosity of at least about 4.0 poise at a shear rate of 100 seconds, and a viscosity of at 20 least about 25.0 poise at a shear rate of lO seconds 1; (ii) a yield point of at least about 2, 500 dynes/cm2; (iii) a thixotropic area of at least about 0.20 x 106 dynes/cm2-sec;
and (iv) a liquid/solid stability of at least about 50~; and (b) an edible, absorbable, digestible food material which acts as a 25 solvent for said fat substitute.
The invention also relates to the fat materials in combination with a food emulsifier capable of forming an oil-in-wat~r emulsion with the fat materials in the mouth.
The compositions of this invention are useful as fat 30 substitutes in low calorie fat-containing food products. The compositions provide a non-waxy taste in the mouth. At the same time, a laxative side effect is avoided without the use of anti-anal leakage agents.
Detailed Descri~f the Invention This invention relates to nonwaxy-tasting compositions useful as fat substitutes for making low calorie food products.
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A
3~3 The compositions do not produce an undesirable laxative side effect. Generally speaking, the invention involves the use of certain edible, wholly or p~rtially nondiges tible low calorie fat materials that are able to retain their viscosity and stability S at rela~vely low solids content levels. Then, these fat materials are made even more palatable by adding either a food material lhat lowers the melting point of the compositîon or a food emulsifier capable of producing an oil-in-water emulsion with the fat materials.
1a It was discovered that some intermediate me1ting low calorie fat materials with pseudoplastic flow properties exhibit unique and unexpected rheology and liquidl solid stability at body temperature. These compositions behave as stable, homogeneous ~on-Newtonian pseudoplastic materials at body 15 temperature. For example, specially synthesized sucrose fatty acid polyesters that were 12% solid and 88% liquid at body temperature (98.6F, 37C) were very viscous and had excellent liquid/ solid stability . This is in contrast to the properties of a mixture containing 88% liquid sucrose polyester 20 and 12% solid sucrose polyester. At body temperature the mixture will separate into liquid and solid portions.
Additionally, this mixture has a low viscosity. The specially synthesized sucrose polyesters, on the other hand, exhibit pseudoplastic flow and surprising viscosity and liquid/ solid 25 stability at relatively low levels of solids. The low calorie fat materials of this invention are thought to be homogeneous systems. While not intended to be bound by theory, evldence of networking between the solid crystals of the materials has been discovered which may be involved in their surprisingly 30 high llquid/solid stability and viscosity at body temperature.
~ benefit of the fat materials' high viscosity and liquid/solid stability is that ingestion of -them does not result in an undesirable laxative side effect. Being viscous and stable, the materials pass from the digestive tract through 35 the anal sphincteI in much the same manner as noImal feces.
3~
Hence, the fat materials of this inven tion can be safely ingested without adding anti-anal leakage agents.
Another benefit accrues from the fact that the present fat materials are able to retain their high viscosity and 5 stability at relatively low solids content levels. It has been found that they are capable of being ingested without a laxative side effect even at Solids Fat Content levels down to about 5%. When the fat substitute compositions are made with low solids content levels, less solids are perceived in the 10 mouth when the compositions are eaten, so foods containing them taste less waxy.
The present invenffon relates to compositions containing these fat materials, in which additional ingredients are added to make compositions in which the taste of the fat materials lS
15 further improved.
A. Description of the Low Calorie Fat Materials By "low calorie fat materials" is meant edible materials which can replace triglyceride fats or oils in the human diet.
These materials provide the benefits of triglyceride fats and 2 0 oils , i . e., lubricity and flavors .
By "wholly nondigestible" is msant that substantially all of the material is not digested by the body. It passes through the digesffve system substantially the same as when it was ingested. The term "partially nondigestible" means 25 that at least about 30% of the material is not digested.
Preferably at least about 70% of the material is not digested.
By "liquid/ solid stability" as used herein is meant that the liquid portion of the material does not reacllly separate from the solid portion at body temperature, i.e., the material 3 appears to be a solid even though up to about 95% of it is liquid. Liquid/solid stability is measured by centrifuging a sample of` the material at 60, 000 rpm for one hour at 100F
(37.8C). Liquid/solid stability is defined as: 100% minus percentage of the material that separated as a liquid after 35 centrifuging.
The present invention is concerned with the rheology of the low calorie fat materials at body temperature ( 98 . 6F, 37C) because they must be stable and viscous at body temperature to eliminate a laxative side effect. However, the S measurements herein were done at 100F (37.8C) as a matter of convenience and for easier calibration of instruments, and the invention is defined in terms of properties at lnOF
(37.8C). It is understood that measurements done at 100F
(37.8C) are very close to measurements at body temperature, 1 a and they conservatively state the rheological properties at body temperature since a lower temperature increases the viscosity .
The fat materials herein exhibit unexpected rheology and liquid/ solid stability at body temperature . For e~ample, specially synthesized intermediate melting sucrose fatty acid polyesters which are 12% solid and 88% liquid at body temperature exhibit non-Newtonian pseudoplastic flow properties, are very viscous and have excellent liquid/ solid stability. This is in contrast to the properties of a mixture containing 88% of a liquid sucrose polyester and 12% of a solid sucrose polyester. At body temperature the mixture of 12%
solid sucrose polyester and 88% liquid sucrose polyester separates into liquid and solid portions. Additionally, the mixture has a low viscosity. The specially synthesized sucrose polyesters, on the other hand, exhibit pseudoplastic flow and surprising viscosity and liquid/ solid stability at relatlvely low levels of solids.
A benefit of the low calorie fat materials' high viscosity and liquid/ solid stability is that ingestion of the materials 3a does not result in an undesirable laxative side effect. Being viscous and stable, the materi~ls pass from the digestive tract through the anal sphincter in much the same manner as normal feces. Ilence, the materials of this invention can be safely ingested without adding anti-anal leakage agents.
3 S Another benefit accrues from the fact that the present fat materials are able to retain their high viscosity and stability at relatively low so}ids content levels. When the compositions are ingested, less solids are perceived in the mouth, so the compositions taste less waxy.
The low calorie fat materials of this invention are s thought to be homogenous systems. While not intended to be bound by theory, evidence of networking between the solid crystals and licluid of the materials has been discovered which may be involved in the surprisingly high liquidl solid stability and viscosity of the materials at body temperature.
1~ The present invention, then, relates to a composition OI
matter comprising an edible, wholly or par~ally nondigestible low calorie fat material having physical chemical properties such that it has a non-Newtonian pseudoplas~c rheology at 100F (37.8C). In particular, at 10ûF (37.8C) the fat material has: ~ a) a viscosity of at least about 2 . 5 poise at a shear rate of 800 seconds, a viscosity of at least about 4.0 poise at a shear rate of 100 seconds 1, and a viscosity of at least about 25 . 0 poise at a shear rate of 10 seconds 1; (b) a yield point of at least about 2 ,500 dynes/cm2; (c) a 2Q thixotropic area of at least about 0.20 x 106 dynes/cm2-sec.;
and (d) a liquid/solid stsbility of at least about 50~.
Viscosity, yield point, and thixotropic area are well known rheological properties, and can be measured by use of an instrument such as a plate and cone viscometer (e. g., a 2 5 Ferranti-Shirley viscometer, manufactured by ~erranti Electric, Inc., 87 Modular Ave., Commack, NY 11725). The basics o~` rheology are discussed in Idson, "Rheology:
Fundamental C:oncepts, " Cosmetics and Toiletries, Vol. 93, pp. 23-30 (July 1978). "Viscosity" is a measure of the internal fIiction resisting the movement of each layer of fluid as lt moves past an adjacent layer of fluid. The "yield value" is the amount of shearing stress that must be applied before a material will begin to flow. Idson defines "thixotropy" as a reversible gel-sol-gel transition caused by 3 5 the building up of a definite structure within the material .
The gelled structure upon shaking or stirring becomes a sol, which when allowed to remain undisturbed, becomes gelled again .
To measure viscosity, yield point, and thixotropic area of a sample of the fat material of this invention, a plate and cone viscometer is used to record a rheogram, which is a plot of shear stress versus shear rate. Viscosity and yield point are calculated from points on the rheogram curve, and the thixotropic area is the area within the curve (also known as the "hysteresis loop"). Additional details lO are provided below under the Analytical Methods section.
Preferably, at 100F (37.8C) the low calorie fat materials of this invention have a viscosity of at least about 5 poise at a shear rate of 800 seconds 1, a viscosity of at least about 20 poise at a shear rate of 100 seconds 1, and a 15 viscosity of at least about 200 poise at a shear rate of 10 seconds . The preferred yield point of the compositions is at least about 5, 000 dynes/cm2, and the preferred thixotropic area is at least about 0.75 x 106 dynes/cm2-sec. Preferably, the compositions have a li~uid/solid stability of at least about 20 9096.
Most preferably, at 100F (37.8C) the low calorie fat materials have a viscosity of at least about 8 poise at a shear rate of 800 seconds 1, a viscosity of at least about 30 poise at a shear rate of 100 seconds 1, and a viscosity of at least 25 about 400 poise at a shear rate of 10 seconds 1. The most preferred yield point of the compositions is at least about 15,000 dynes/cm2, and the most preferred thixotropic area is at least about 1.00 x 106 dynes/cm2-sec.
The preferred upper limit of the viscosity of the fat 30 materials of this invention is about 1 x 105 poise at a shear rate of lO seconds 1, and about 1,000 poise at a shear rate of 100 seconds 1 The fat materials must have pseudoplastic flow properties as deflned herein.
.~
3~3 Iodine Value is a measure of the degree of unsaturation of atty acids. The low calorie fat materials of this invention preferably have an Iodine Value of from about 36 to about 55.
The Solid Fat Content value (SFC) provides a reasorIable S approximation of the percent by weight solids of a particular fatty material at a given temperature. The present low calorie fat material preferably has a Solid Fat Content at 100F (37.8C) of at least about 5%. Most preferably, the Solid Fat Content at 100F (37 . 8C) is at least aboùt 10% ~
The low calorie fat material preferably has a complete melting point higher than about 98.6F (37~C).
The low calorie fat materials of the present invention can be any of a variety of edible, wholly or partially nondiges-tible compounds. Preferably, the fat material is selected from the group consisffng of polyol fatty acid polyesters and polycarboxylic acids esterified with fatty alcohols, and mixtures thereof. Preferred polyol fatty acid polyesters are sugar fatty acid polyesters, sugar alcohol fatty acid polyesters, and polyglycerol fatty acid polyesters, and 2 0 mixtures thereof . More preferably, the fat material is selected from the group consisting of sugar fatty acid polyesters and sugar alcohol fatty acid polyesters, and mixtures thereof, the sugars and sugar alcohols containing from 4 to 8 hydroxyl groups.
Su~ar or sugar nlcohol fatty acid polyes~ers comprise sugars or sugar alcohols, nnd fatty acids. The term "sugar"
is used herein in its conventional sense as generia to mono-and disaccharides. The term "sugar alcohol" is also used in its conventional sense as generic to the reduction product of 3 0 sugars wherein the aldehyde or ketone group has been reduced to an alcohol. The fatty acid ester compounds are prepared by reacting a monosaccharide, disaccharide or sugar alcohol with fatty acids as discussed below.
Examples of suitable monosaccharides are those containing 4 hydroxyl groups such as xylose, arabinose, and ribose; the sugar alcohol derived from xylose, i.e., xylitol, ~2~
is also suitable. The monosaccharide erythrose is not suitable for the practice of this inven tion since it only contains 3 hydroxyl groups; however, the sugar alcohol derived from erythrose, i . e . erythritol, contains 4 hydroxyl groups and is 5 thus suitable. Among 5 hydroxyl-containing monosaccharides that ar0 suitable for use herein are glucose, mannose, galactose, fructose, and sorbose. A su~ar alcohol dlerived from sucrose, glucose, or sorbose, e. g., sorbitol, comtains 6 hydroxyl groups and is also suitable as the alcohol moiety of 10 the fatty acid ester compound. Examples of suitable disaccharides are maltose, lactose, and sucrose, all of which contain 8 hydroxyl groups.
In preparing sugar or sugar alcohol fatty acid polyesters of the present invention a sugar or sugar alcohol compound 15 such as those identified above must be esterified with a mixture of fatty acids having from about 8 to about 22 carbon atoms. Examples of such fatty acids are caprylic, capric, lauric, myristic, myristoleic, palmitic, palmitoleic, stearic, oleic, ricinoleic, linoleic, linolenic, eleostearic, arachidic, 20 behenic, and erucic. The fatty acids can be derived from suitable naturally occurring or synthetic fatty acids and can be saturated or unsaturated, including positional and geomPtric isomers. The fat materials of this invention are mixed esters of fatty acids, rather than esters of a single 25 type of fatty acid.
~ atty acids per se or nflturally occurring fats and oils can serve as the source for the fatty acid component in the sugar or sugar alcohol fatty acid ester. For example, rap0seed oil provides a good source for C22 fatty acid.
30 C16-C18 fatty acid can be provided by tallow, soybean oil, or cottonseed oil. Shorter chain fatty acids can be provided by coconut, palm kernel, or babassu oils. Corn oil, lard, olive oil, palm oil, peanut oil, safflower seed oil, sesame seed oil, and sunflower seed oil, are examples of other natural oils 35 which can serve as the source of the fatty acid component.
3~
The sugar or sugar alcohol fatty acid polyesters suitable for use herein can be prepared by a variety of methods well known to those skilled in the art. These method include:
transesterification of the sugar or sugar alcohol with methyl, S ethyl or glycerol fatty acid esters using a variety of catalysts; acylation of the sugar or sugar alcohol with a fatty acid chloride; acylation of the sugar or sugar alcohol with a fatty acid anhydride; and acylation of the sugar or sugar alcohol with a fatty acid, per se. As an example, the 10 preparation of sugar and sugar alcohol fatty acid esters is described in U.S. Pat. No. 2,831,854.
A characterizing feature of the sugar or sugar alcohol fatty acid polyesters useful in this invention is that they predominantly contain at least 4 fatty acid polyester groups.
15 Sugar or sugar alcohol fatty acid polyester compounds that contain 3 or less fatty acid estèr groups are digested in the intestinal tract much in the manner as ordinary triglyceride fats, but sugar or sugar alcohol fatty acid polyester compounds that contain four or more fatty acid ester groups 20 are digested to a lesser extent and thus have the desired low calorie properties for use in this invention.
Highly preferred low calorie fat materials according to this invenffon are sucrose fatty acid polyesters. Preferred sucrose fatty acid polyesters have the majority of their 25 hydroxyl groups esteri'ded with fatty acids. Preferably at least about 80~, and most preferably at least about 95~, of the sucrose fatty ncid pol~resters are selected from the group consisting of octaesters, heptaesters and hexaesters, and mixtures thereo~. Preferably, no more than about 35% of the 30 esters are hexaesters or heptaesters, and at least about 6096 of the sucrose fatty acid polyesters are octaesters. Most preferably, at least about 70% of the polyesters are octaesters .
In order to provide the required physical properties, the 35 sucrose fatty acid polyesters of this invention are preferably esterified with particular kinds of fatty acids. Preferably, at ~2~3~
least about 80~, and most preferably at least about 90~, of the fatty acids are selected from the group consistin~ of mixtures of palmitic, stearic, oleic, linoleic, and behenic acids .
More specifically, the following is a preferred fatty acid composition: from about 9% to about 12~ palmitic; from about 35% to about 53% stearic; from about 19% to about 43% oleic;
from about 2% to about 17% linoleic; from about 0% to about 2g6 linolenic; from about 0% to about 2P~ arachidic; from about 0%
to about 10% behenic; and from about 0% to about 2~ erucic.
The fo~owing fatty acid composition is most preferred:
from about 9~ to about 12~ palmitic; from about 42% to about 53% stearic; from about 19% to about 39% oleic; from about 2%
to about 17% linoleic; from about 0% to about 2% linolenic; from L5 about 0% to about 2% arachidic; from about 0% to about 10%
behenic; and from about 0% to about 2% erucic.
Polyglycerol fatty acid polyesters can also be low calorie fat materials of the present invention. Polyglycerol is prepared by the polymerization of glycerine in the presence of either acid or base. The polyglycerols can contain from 2 to 20 glycerol moieties. Preferably, the polyglycerols will be those having from 2 to 15 glycerol moieties.
The polyglycerol compounds can be made by any synthetic method . S ee, for example, U . S . 3, 9 68 ,169 to 2 5 Seiden and Martin ( 1976 ) . Esterification of the polyglycerols can also be done by any method known to the art, providing the resulting polyglycerol esters have the rheological properties required of the present invention.
Anlmal s tudies have now shown polyglycerol esters with 3 0 the eollowin~ rheological properties to be very effective at eliminating laxative side efeect: ta) a viscosity of 3.13 poise at a shear rate of 800 seconds 1, a viscosity of 5.18 poise at a shear rate of 100 seconds 1, and a viscosity of 32.43 poise at a shear rate of 10 seconds 1; (b) a thixotropic area of 3s 0.246 x 106 dynes/cm2-sec.; and (c) a liquid/solid stability of 53 . 45% .
3~3 Th~ "polycarboxylic acids esterified with fatty alcohols"
are tricarboxylic and tetracarboxylic acids and higher. The polycarbo~cylic acids can be partially or wholl3r esterified with fatty alcohols. At least three fatty alcohol ester groups must be on an acid molecule to make it partially nondigestible.
B. Methods for Making the Fat Materials Better Tasting While the fat materials of this invention offer an improvement in non-waxy taste when used alone in a food product, this invention relates to methods for making the fat substitutes even better-tasting than they are alone.
One method involves the use of an edible, absorbable, digestible food material which acts as a solvent for the fat substitute. It was discovered that by the addition of a food material such as a liquid triglyceride to the fat materials, the melting point of the materials is lowered, so that at mouth temperature (92F, 33.3C) the fat materials have a Solid Fat Content less than about 20~. Hence, when the fat materials are ingested they do not taste waxy in the mouth. After being ingested, the food material that acts as a solvent is 2 digested in the stomach and intestines, and the melting point reduction effect is thereby eliminated. The fat materials revert to their original solids content in the gastrointestinal tract. When the fat materials pass from the colon, then, they are viscous and stable enough to not cause a laxative side 2 5 effect .
Therefore, one aspect of the present invention is a composition of matter having a Solid Fat Content less than about 20% at mouth temperature (92F, 33.3C), comprising:
(a) an edible, wholly or partially nondigestible low calorie fat material having, at 100F (37.8C): (i) a viscosity of at least about 2 . 5 poise at a shear rate of 800 seconds 1, a viscosity of at least about ~ . 0 poise at a shear rate of 100 seconds 1, ancl a viscosity of at least about 25 . O poise at a shear rate of 10 seconds 1; (ii) a yield point of at least about 2,500 dynes/cm2; (iii) a thixotropic area of at least about 0.20 x 106 dynes/cm~-sec; and (iv) a liquid/solid stability of 3~
at least about 50%; and (b) an edible, absorbable, digestible food material which acts as a solvent for said fat substitute.
For very good non-waxy taste in the mouth, it is preferable that the composition have a Solid Fat Content less than about 10% at mouth temperature (92F, 33.3C), and most preferably less than about 5%.
The edible, absorbable, digestible food material which acts as a solvent for the fat substitute is preferably selected from the group consisting of triglycerides, monoglycerides, diglycerides, substituted mono- and diglycerides, polyglycerol esters, citrus oils, flavorants, edihle alcohols, edible food emulsifiers, and mixtures thereof. Most preferably, the food material is selected from the group consisting of triglycerides and substituted mono- and diglycerides, and mixtures thereof. By "substituted" mono- and diglycerides is meant mono- and diglycerides in which the free hydroxyl groups are substituted with edible short chain fatty acids , i. e., C2 through C8.
Edible food emulsifiers include mono- and diglycerides, lower sucrose esters (C1- C4), and lower polyglycerol esters (C -C ) The digestible food material must be capable of lowering the melting point ( freezing point) of the fat materials .
Freezing point depression generally follows the formula: I/T
= I/To ~ (R In x/delta Hf)~ where T = treezing point, To =
pure freezing point, X = mole fraction, and delta Hf = heat of fusion .
The amount and type Oe digestible food material usad as a solvent will depend on the end food product ln which the composition of this invention will be used. For example, a preferred food material for this purpose is triglycerides. In a margarine prodllct what is desired is a low Solid Fat Content and a fairly low viscosity. There is an optimum visco~ity so that the margarine is thin enough so that the saliva in the mouth can act on it and make it invert. If the margarine is too thin, it will disperse in the mouth before the P9~
saliva is able to act on it. As another example, shortening must have substantial plasticity because of its use in the areas of frying and baking. Yet, the shortening should not be so ~lrm as to taste very firm in the mouth. In summary, 5 a specific triglyceride or other food material is picked depending on the food product in which it will be used.
I t has been discovered that particular raffos of triglyceride and fat substitute (in particular sucrose polyesters) are desirable in terms of calorie reduction. To 10 maximize the calorie reduction benefit, from about 67~ to about 90% of the sucrose polyester is combined with from about 33% to about 10~ triglyceride. To obtain the minimum reduced calorie benefit that is allowed by current Government re gulations, from about 33% to about 90% sucrose polyester is combined with from about 66~6 to about 10% triglyceride.
The other method of this invention, for making the low calorie fat materials even more palatable, comprises ad~ing to the fat materials an edible, digesffble food emulsifier capable of forming an oil-in-water emulsion with the fat materials in 20 the mouth. Saliva from the mouth and any water in the food comprises the water portion of the emulsion, while the present fat material and any oil from the food comprises the oil part.
When the fat material is made into an oil-in-water emulsion with saliva, it does not taste waxy in the mouth. After 25 ingesffon, the food emulsifier is digested whi~e the fat material remains undigested, so the ~at material reverts tc. its original form. A good-tasting food product can be made that does not produce a laxative side effect.
Tendency of an emulsifier to form an oil-in-water 3~ emulsion is measured by its hydrophilic/lipophilic balance (HLB). The ernulsifler used in the composition of this invention must have an HL~3 value of at least 2.
Preferred food emulsifiers for use herein are selected from the group consisting of mono- and diglycerides, lower 35 sucrose esters, lower polyglycerol esters, and mixtures thereof .
3~
The compositions of the present invention can be used as a partial or total replacement for normdl triglyceride fat in any fat-containing food composition to provide low calorie benefits. In order to obtain a significant low calorie effect, 5 it is necessary that at least about 10% of the fat in the food composition comprises the present compositions. On the other hand, very low calorie and thus highly desirable food compositions of the invention are obtained when the fat comprises up to about 100% of the composiffons of this 10 invention. Hence, the compositions of the present invention can be used as a parffal or complete replacement for normal triglyceride fat in a salad or cooking oil, or a plastic shortening, or the like. The compositions can also be used as a partial or complete replacement for normal triglyceride 15 fat in fat-containing food products such as mayonnaise, margarine, and dairy products.
.~
, ~Z9~'~3~3 Analytical Methods I. Rheolo~y Measurements A. Sample Preparation The low calorie fat material is melted in a microwave oven at about 150F (66~C) to about 170F (77C). This takes approximately 2 minutes. The melted fat material is held at 100F + 5F (37.8C + 3C), and a 3 gram sample is weighed into a SoloR plastic souffle cup. The sample is then allowed to recrystallize at 100F + 5F (37.8C + 3C) for 24 hours. After the 24 hour time period has elapsed, the sample is taken to the viscometer in an insulated cup and the viscosity is measured.
B. Ferranti-Shirley Viscometer Operation Procedure A Ferranti-Shirley viscometer is used for the viscosity, yield point, and thixotropic area measurements. A cone is put into place, and the viscometer temperature is adjusted to 100F (37.8C). The chart recorder is calibrated, and the gap between the cone and plate is set. The cone speed is checked, and the cone and plate temperatures are equilibrated to 100F (37.8C). The panel controls are set. Sufficient sample is placed between the plate and the cone so that the gap is completely filled. The temperature is allowed to stabilize at 100F (37.8C) for about 30 seconds, and then the cone rotation and recording are started. A rheogram for the fat material is recorded and analyzed to determine the viscosity, yield point, and thixotropic area. Viscosity is measured at shear ratcs of 800 seconds 1, 100 seconds 1, and 10 séconds .
II. LiquidtSolid Stability Messurement 3 The sample is heated until it completely melts and is thoroughly mixed. The sample is then poured into centrifuge tubes at 100F + 5F. The samples then are allowed to recrystallize for 24 hours at 10QF + 5F. The samples are then centrifuged at 50,000 rpm for one hour at 37C. The percent liquid separated is then measured by comparing the relative heights of the liquid and solid phases.
.?~ 4L38 III. Solid Fat Content Measurement Before determining SFC values, the fat material sample is heated to a temperature of 158F (70C3 or higher for at least O . S hours or until the sample is completely melted . The 5 melted sample is then tempered at a temperature of 40F
(4.4C~ for at least 72 hours. After tempering, the SFC
value of the fat material at a temperature of 100F ~37.8C) i8 determined by pulsed nuclear magneffc resonance (PNMR3.
The method for determining SFC values of a fat by PNMR is 1 0 described in Madison and Hill , J . Amer . Oil . Chem . Soc ., Vol. 55 (1978), pp. 328-31.
The following Examples are intended to be further illustrative but not limiting of the present invenffon.
Example 1 Methyl esters of a fully hydrogenated soy oil and a partially hydrogenated soy oil, blended in a 45/55 ratio (227.3 kg), and 36 kg. of an 18 wt. percent solu~on of potassium hydroxide in methanol are mixed in a stainless steel batch reactor. This mixture is then heated to 122F (50C) with 20 a~itation for 1 to 2 hours at atmospheric pressure. During this time, a portion of the methyl esters are saponified. A
vacuum is then pu~led on the system to remove the last traces of methanol.
Granular sucrose (95.5 kg.) is added to the soap/ester 25 mixture to give a 5 :1 molar ratio of ester to sucrose.
Potassium carbonate is then add~d to the mixture (approx.
0 . 5 wt . percent of the reaction mix) to catalyze the transesterificaffon. This mixture is agitated and heated under vacuum at about 275F (135C) for up to 8 hours to 30 form the mono-, di- and trisucrose esters. Small quantities OI tetrn- and pentaesters are also formed during this stage.
Additional methyl ester (276.7 kg) which has been preheated to 275F (135C) is added to bring and malntain the molar ratio of the esters to sucrose to 12 :1. When the reaction 1~. '.
3~3 conditions stabilize at 275F (135C), a nitrogen sparge is used to improve agitation and promote methanol StFipping. As the r~action occurs, the reaction mixture becomes viscous and then thins out. This second reaction stage lasts s approximately 24 to 36 hours.
After the reac1ion mixture h~s become thin, it is cooled to between 149F (65C) and 185F (85C). The crude reaction mixture is agitated with a dilute solution of methanol, sodium chloride and water. The volume of thi~ wash solution is equal to 20% to 40% of the reaction mixture volume. The mixed phases are then allowed to settle for approximately 3 0 to 60 minutes. The lower settled phase which cont~ins the soaps, excess sugars and methanol i8 drawn off and discarded. The upper settled phase which comprises the rafined sucrose polyesters is washed again. Usually 2 to 4 washes are used.
The sucrose polyesters are then washed with a 1~ glacial acetic acid in water solution at 10% to 20% of the volume of the reaction mix. This is fo~owed by water wash of the same 2 0 volume .
The reaction mix is then dried to remo~re moisture at 176F (80C) under 10 mm Hg or less vacuum for 30 to 60 minutes . Filtrol 10~( 0 . 5 wt . percent), and a filter aid ( 0 . 5 wt. percent) are added and the mix is agitated at 167F
(75C) to 185F (85C). The slurry is separated by filtra'don or other mean~ until there is less than 0.1 wt. percent fines.
The li~uid is then passed through a 1 micromillimeter filter.
The refined and bleached reaction mix is then returned to the stainless steel batch reactor to distill off the buhlc of the methyl esters. The distilla'don takes place at 374F
(190C) to 482F (250C) under approximately 5 mm Hg of vacuum. This step is complste when it is visually evident that the distillation has slowed down.
The ~ucrose polyester is then deodorized in a stainless steel batch deodorizer or other suitable device at 374F
(19ûC) to 482F (250C) under a vacuum of about 5 mm Hg 3~
-zo-with steam sparging. Deodori~ation is continued until the methyl ester content is helow 200 ppm. The deodorizer contents are then cooled while using inert gas sparging.
After cooling to 149F (65C), the deodorizer is brought to atmospheric pressure. The sucrose polyester is stored in clean stainless stesl drums.
This produces a sucrose polyester product having the fatty acid composition specified in Table I. Rheology and effectiveness at preventing laxative side effect are listed in 1~ Table 2.
Example 2 Methyl esters of a fully hydrogenated soy oil and a touch hardened soy oil, blended in a 55/45 ratio (16 kg), and 2 kg. of an 15 wt. percent solution of potassium hydroxide in methanol are mixed in a stainless steel batch reactor. This mixture is then heated to 86F (30C) with agitation for 1 to 2 hours at atmospheric pressure. During this time, a portion of the methyl esters are saponified. A vacuum is then pulled on the system to remove the last traces of methanol.
Powdered sucrose (3 kg.) is added to the soap/ester mixture to give a 6 :1 molar ratio of ester to sucrose.
Potassium carbonate is then added to the mixture ( approx .
0 . 5 wt . percent of the reactlon mix) to catalyze the transesterification. This mixture is agitated and heated under vacuum at about 275F (135C) ~or up to 2-1/2 hours to form the mono-, di- and trisucrose esters. Small quantities of tetra- and pentaesters are also formed during this stage. Additional methyl ester (19.5 kg) which has been preheated to 275F (135C) is added to bring and maintain the molar ratio of the esters to sucrose to 12:1. When the reaction conditions stabilize at 275F (135C), a nitrogen sparge is used to improve a~itation and promote methanol stripping. As the reaction occurs, the reaction mixture becomes viscous and then thins out. This second reaction stage lasts approximately 4 to 8 hours.
After the reaction mixture has become thin, it is cooled to between 149F (65C) and 185F (85C). The crude reaction mixture is agitated with a dilute solution of methanol~
sodi~m chloride and water. The volume of this wash solution is equal to 20Q6 to 40% of the reaction mixture volume. The mixed phases are then allowed to settle for approximately 3 0 to 60 minutes. The lower settled phaqe which contains the soaps, excess sugars and methanol is drawn off and discarded. The upper settled phase which comprise~ the 1 Q refined sucrose polyesters is washed again . Usua~ly 2 to 4 washes are used.
The sucrose polyesters are then washed with a 1% glacial acetic acid in water solution at 10% to 20% of the ~rolume of the reaction mix. This is followed by water wash of the same volume.
The reaction mix is then dried to remove moisture at 176F (80C) under 10 mm Hg or less vacuum for 30 to 60 minutes. Filtrol 105 (0.5 wt. percent), and a filter aid (0.5 wt. percent) are added and the mix is agitated at 167F
(75C) to 185F (85C). The slurry is separated by filtration or other means until there is less than 0.1 wt. percent fines.
The liquid is then passed through a 1 micromillimeter filter.
The refined and bleached reaction mix is put into a stainless steel batch deodorizer to distill off the bulk of the methyl esters. The distillation takes place at 374F (190C) to 482F (250C) under approximately 5 mm Hg of vacuum.
This step is complete when it is visually evident that the distillation has slowed down.
The sucrose polyester is then deodorized in a stainless steel batch deodorizer or other suitable device at 374F
(190C) to 482F (250C) under a vacuum of about 5 mm Hg with steam sparging. Deodorlzation is continued until the methyl ester content is below 200 ppm. The deodorizer contents are then cooled while using inert gas sparging.
After cooling to 149F (65C), the deodorizer is brought to atmospheric pressure. The sucrose polyester is stored in clean stainless steel drums.
This produces a sucrose polyester product having the fatty acid composition specified in Table I. Rheology and 5 effectiveness at preventing laxative side effect are listed in Table II.
The results shown in Tables I and II i31ustrate that sucrose polyesters prepared accordin~ to Examples 1 and 2 have the properties of the low calorie fat materials of the 1 Q present invention . The third column in Table I shows the properties of a liquid sucrose polyester prepared according to a method known to the art, and not falling within the present invention .
Table II compares the rheology and effecffveness at 15 prevenffng laxative side effect of the three samples.
Examples 1 and 2 have rheological properties according to this invention; the liquid sucrose polyester does not. The liquid sucrose polyester results in a 15% oil loss when ingested. By contrast, the sucrose polyesters prepared in Examples 1 and 20 2 result in 0% oil loss, showing that they are very effective at eliminating laxative side effect.
When the sucrose polyesters of Examples 1 and 2 are mixed with triglyceride in a ratio of 75% sucrose polyester and 25% triglyceride, a composition is made that tastes very good 25 when ingested and that does not cause a laxative side efeect.
3~3 T able Sucrose Polyester Composition Liquid Sucrose Example 1Example 2Polyester Fatty Acid Composition % % %
Others 2.4 2.3 3.4 C 11.4 9.4 8.6 C16 44.0 50.8 5.7 10 C 8 37.2 20.4 45.6 c1~8.2 2.6 14.8 31.7 C 0.6 0.3 0.
c20 3 0.6 0.6 0.6 C22 1.2 1.4 0.0 15 I.V. 38.2 47.6 62.6 Ester Distribution % % 96 Octa 94.5 79.0 71.1 Hepta 5.6 19.2 24.0 Hexa 0.0 1.8 4.9 Penta 0.1 0.1 0.1 ~ Penta 0.1 0.1 0.1 SFC Profile % % %
F. 67.6 64.3 0 2570 F. 55.2 53.6 0 F. 44.2 43.0 0 92 F. 23.3 21.1 0 105 F. 5.2 2.7 0 98.6 F. 14.3 11.9 0 30 DSC Behavior C. C. C.
~ . . .. .... . _ .
Complete Melt Point38.9 42.5 -20.0 Maximum Melt Point36.0 39.4 -35.0 35 H eat of Fusion 14.8 11.7 10.6 -o~a R ¦ o ¢
~ C~
x ~ E X x ~a ~
l_ ~' ~ ~
O,~ _~
.
~ 3) o ''~
~ ~a ~ 0~O 0 0 ~
~i a
It is therefore an cibject oî an aspect of the present invention to provide a cc~T~osition, use~ul as a fat substitute ~n foods, ~ich does not taste wa~y in the m~lth ~en ingested.
It is an object of an aspect s~ this ~vention to provide a 5 c~mposition made with law calorie fat materials, so that food pr~ducts made with the car~osition are l~w in calories.
It is an object of an aspect of the pr~sent invention to avoid a laxative side effect withaut hav~ng to add anti-anal lealcage agents.
mese and c~ther bbjects of the ~vention will be made clear by the disclosure herein.
Summary of the Invention The present invention is a composition of matter having a Solid Fat Content less than about 20% at mouth temperature 15 (92F~ 33.3~C), comprising: (a) an edible, wholly or partia~y nondigestible low calorie fat materisl having, at 100F
(37.8C): (i) a viscosity of at least about 2.5 poise at a shear rate of 800 seconds 1, a viscosity of at least about 4.0 poise at a shear rate of 100 seconds, and a viscosity of at 20 least about 25.0 poise at a shear rate of lO seconds 1; (ii) a yield point of at least about 2, 500 dynes/cm2; (iii) a thixotropic area of at least about 0.20 x 106 dynes/cm2-sec;
and (iv) a liquid/solid stability of at least about 50~; and (b) an edible, absorbable, digestible food material which acts as a 25 solvent for said fat substitute.
The invention also relates to the fat materials in combination with a food emulsifier capable of forming an oil-in-wat~r emulsion with the fat materials in the mouth.
The compositions of this invention are useful as fat 30 substitutes in low calorie fat-containing food products. The compositions provide a non-waxy taste in the mouth. At the same time, a laxative side effect is avoided without the use of anti-anal leakage agents.
Detailed Descri~f the Invention This invention relates to nonwaxy-tasting compositions useful as fat substitutes for making low calorie food products.
x, ,il~
A
3~3 The compositions do not produce an undesirable laxative side effect. Generally speaking, the invention involves the use of certain edible, wholly or p~rtially nondiges tible low calorie fat materials that are able to retain their viscosity and stability S at rela~vely low solids content levels. Then, these fat materials are made even more palatable by adding either a food material lhat lowers the melting point of the compositîon or a food emulsifier capable of producing an oil-in-water emulsion with the fat materials.
1a It was discovered that some intermediate me1ting low calorie fat materials with pseudoplastic flow properties exhibit unique and unexpected rheology and liquidl solid stability at body temperature. These compositions behave as stable, homogeneous ~on-Newtonian pseudoplastic materials at body 15 temperature. For example, specially synthesized sucrose fatty acid polyesters that were 12% solid and 88% liquid at body temperature (98.6F, 37C) were very viscous and had excellent liquid/ solid stability . This is in contrast to the properties of a mixture containing 88% liquid sucrose polyester 20 and 12% solid sucrose polyester. At body temperature the mixture will separate into liquid and solid portions.
Additionally, this mixture has a low viscosity. The specially synthesized sucrose polyesters, on the other hand, exhibit pseudoplastic flow and surprising viscosity and liquid/ solid 25 stability at relatively low levels of solids. The low calorie fat materials of this invention are thought to be homogeneous systems. While not intended to be bound by theory, evldence of networking between the solid crystals of the materials has been discovered which may be involved in their surprisingly 30 high llquid/solid stability and viscosity at body temperature.
~ benefit of the fat materials' high viscosity and liquid/solid stability is that ingestion of -them does not result in an undesirable laxative side effect. Being viscous and stable, the materials pass from the digestive tract through 35 the anal sphincteI in much the same manner as noImal feces.
3~
Hence, the fat materials of this inven tion can be safely ingested without adding anti-anal leakage agents.
Another benefit accrues from the fact that the present fat materials are able to retain their high viscosity and 5 stability at relatively low solids content levels. It has been found that they are capable of being ingested without a laxative side effect even at Solids Fat Content levels down to about 5%. When the fat substitute compositions are made with low solids content levels, less solids are perceived in the 10 mouth when the compositions are eaten, so foods containing them taste less waxy.
The present invenffon relates to compositions containing these fat materials, in which additional ingredients are added to make compositions in which the taste of the fat materials lS
15 further improved.
A. Description of the Low Calorie Fat Materials By "low calorie fat materials" is meant edible materials which can replace triglyceride fats or oils in the human diet.
These materials provide the benefits of triglyceride fats and 2 0 oils , i . e., lubricity and flavors .
By "wholly nondigestible" is msant that substantially all of the material is not digested by the body. It passes through the digesffve system substantially the same as when it was ingested. The term "partially nondigestible" means 25 that at least about 30% of the material is not digested.
Preferably at least about 70% of the material is not digested.
By "liquid/ solid stability" as used herein is meant that the liquid portion of the material does not reacllly separate from the solid portion at body temperature, i.e., the material 3 appears to be a solid even though up to about 95% of it is liquid. Liquid/solid stability is measured by centrifuging a sample of` the material at 60, 000 rpm for one hour at 100F
(37.8C). Liquid/solid stability is defined as: 100% minus percentage of the material that separated as a liquid after 35 centrifuging.
The present invention is concerned with the rheology of the low calorie fat materials at body temperature ( 98 . 6F, 37C) because they must be stable and viscous at body temperature to eliminate a laxative side effect. However, the S measurements herein were done at 100F (37.8C) as a matter of convenience and for easier calibration of instruments, and the invention is defined in terms of properties at lnOF
(37.8C). It is understood that measurements done at 100F
(37.8C) are very close to measurements at body temperature, 1 a and they conservatively state the rheological properties at body temperature since a lower temperature increases the viscosity .
The fat materials herein exhibit unexpected rheology and liquid/ solid stability at body temperature . For e~ample, specially synthesized intermediate melting sucrose fatty acid polyesters which are 12% solid and 88% liquid at body temperature exhibit non-Newtonian pseudoplastic flow properties, are very viscous and have excellent liquid/ solid stability. This is in contrast to the properties of a mixture containing 88% of a liquid sucrose polyester and 12% of a solid sucrose polyester. At body temperature the mixture of 12%
solid sucrose polyester and 88% liquid sucrose polyester separates into liquid and solid portions. Additionally, the mixture has a low viscosity. The specially synthesized sucrose polyesters, on the other hand, exhibit pseudoplastic flow and surprising viscosity and liquid/ solid stability at relatlvely low levels of solids.
A benefit of the low calorie fat materials' high viscosity and liquid/ solid stability is that ingestion of the materials 3a does not result in an undesirable laxative side effect. Being viscous and stable, the materi~ls pass from the digestive tract through the anal sphincter in much the same manner as normal feces. Ilence, the materials of this invention can be safely ingested without adding anti-anal leakage agents.
3 S Another benefit accrues from the fact that the present fat materials are able to retain their high viscosity and stability at relatively low so}ids content levels. When the compositions are ingested, less solids are perceived in the mouth, so the compositions taste less waxy.
The low calorie fat materials of this invention are s thought to be homogenous systems. While not intended to be bound by theory, evidence of networking between the solid crystals and licluid of the materials has been discovered which may be involved in the surprisingly high liquidl solid stability and viscosity of the materials at body temperature.
1~ The present invention, then, relates to a composition OI
matter comprising an edible, wholly or par~ally nondigestible low calorie fat material having physical chemical properties such that it has a non-Newtonian pseudoplas~c rheology at 100F (37.8C). In particular, at 10ûF (37.8C) the fat material has: ~ a) a viscosity of at least about 2 . 5 poise at a shear rate of 800 seconds, a viscosity of at least about 4.0 poise at a shear rate of 100 seconds 1, and a viscosity of at least about 25 . 0 poise at a shear rate of 10 seconds 1; (b) a yield point of at least about 2 ,500 dynes/cm2; (c) a 2Q thixotropic area of at least about 0.20 x 106 dynes/cm2-sec.;
and (d) a liquid/solid stsbility of at least about 50~.
Viscosity, yield point, and thixotropic area are well known rheological properties, and can be measured by use of an instrument such as a plate and cone viscometer (e. g., a 2 5 Ferranti-Shirley viscometer, manufactured by ~erranti Electric, Inc., 87 Modular Ave., Commack, NY 11725). The basics o~` rheology are discussed in Idson, "Rheology:
Fundamental C:oncepts, " Cosmetics and Toiletries, Vol. 93, pp. 23-30 (July 1978). "Viscosity" is a measure of the internal fIiction resisting the movement of each layer of fluid as lt moves past an adjacent layer of fluid. The "yield value" is the amount of shearing stress that must be applied before a material will begin to flow. Idson defines "thixotropy" as a reversible gel-sol-gel transition caused by 3 5 the building up of a definite structure within the material .
The gelled structure upon shaking or stirring becomes a sol, which when allowed to remain undisturbed, becomes gelled again .
To measure viscosity, yield point, and thixotropic area of a sample of the fat material of this invention, a plate and cone viscometer is used to record a rheogram, which is a plot of shear stress versus shear rate. Viscosity and yield point are calculated from points on the rheogram curve, and the thixotropic area is the area within the curve (also known as the "hysteresis loop"). Additional details lO are provided below under the Analytical Methods section.
Preferably, at 100F (37.8C) the low calorie fat materials of this invention have a viscosity of at least about 5 poise at a shear rate of 800 seconds 1, a viscosity of at least about 20 poise at a shear rate of 100 seconds 1, and a 15 viscosity of at least about 200 poise at a shear rate of 10 seconds . The preferred yield point of the compositions is at least about 5, 000 dynes/cm2, and the preferred thixotropic area is at least about 0.75 x 106 dynes/cm2-sec. Preferably, the compositions have a li~uid/solid stability of at least about 20 9096.
Most preferably, at 100F (37.8C) the low calorie fat materials have a viscosity of at least about 8 poise at a shear rate of 800 seconds 1, a viscosity of at least about 30 poise at a shear rate of 100 seconds 1, and a viscosity of at least 25 about 400 poise at a shear rate of 10 seconds 1. The most preferred yield point of the compositions is at least about 15,000 dynes/cm2, and the most preferred thixotropic area is at least about 1.00 x 106 dynes/cm2-sec.
The preferred upper limit of the viscosity of the fat 30 materials of this invention is about 1 x 105 poise at a shear rate of lO seconds 1, and about 1,000 poise at a shear rate of 100 seconds 1 The fat materials must have pseudoplastic flow properties as deflned herein.
.~
3~3 Iodine Value is a measure of the degree of unsaturation of atty acids. The low calorie fat materials of this invention preferably have an Iodine Value of from about 36 to about 55.
The Solid Fat Content value (SFC) provides a reasorIable S approximation of the percent by weight solids of a particular fatty material at a given temperature. The present low calorie fat material preferably has a Solid Fat Content at 100F (37.8C) of at least about 5%. Most preferably, the Solid Fat Content at 100F (37 . 8C) is at least aboùt 10% ~
The low calorie fat material preferably has a complete melting point higher than about 98.6F (37~C).
The low calorie fat materials of the present invention can be any of a variety of edible, wholly or partially nondiges-tible compounds. Preferably, the fat material is selected from the group consisffng of polyol fatty acid polyesters and polycarboxylic acids esterified with fatty alcohols, and mixtures thereof. Preferred polyol fatty acid polyesters are sugar fatty acid polyesters, sugar alcohol fatty acid polyesters, and polyglycerol fatty acid polyesters, and 2 0 mixtures thereof . More preferably, the fat material is selected from the group consisting of sugar fatty acid polyesters and sugar alcohol fatty acid polyesters, and mixtures thereof, the sugars and sugar alcohols containing from 4 to 8 hydroxyl groups.
Su~ar or sugar nlcohol fatty acid polyes~ers comprise sugars or sugar alcohols, nnd fatty acids. The term "sugar"
is used herein in its conventional sense as generia to mono-and disaccharides. The term "sugar alcohol" is also used in its conventional sense as generic to the reduction product of 3 0 sugars wherein the aldehyde or ketone group has been reduced to an alcohol. The fatty acid ester compounds are prepared by reacting a monosaccharide, disaccharide or sugar alcohol with fatty acids as discussed below.
Examples of suitable monosaccharides are those containing 4 hydroxyl groups such as xylose, arabinose, and ribose; the sugar alcohol derived from xylose, i.e., xylitol, ~2~
is also suitable. The monosaccharide erythrose is not suitable for the practice of this inven tion since it only contains 3 hydroxyl groups; however, the sugar alcohol derived from erythrose, i . e . erythritol, contains 4 hydroxyl groups and is 5 thus suitable. Among 5 hydroxyl-containing monosaccharides that ar0 suitable for use herein are glucose, mannose, galactose, fructose, and sorbose. A su~ar alcohol dlerived from sucrose, glucose, or sorbose, e. g., sorbitol, comtains 6 hydroxyl groups and is also suitable as the alcohol moiety of 10 the fatty acid ester compound. Examples of suitable disaccharides are maltose, lactose, and sucrose, all of which contain 8 hydroxyl groups.
In preparing sugar or sugar alcohol fatty acid polyesters of the present invention a sugar or sugar alcohol compound 15 such as those identified above must be esterified with a mixture of fatty acids having from about 8 to about 22 carbon atoms. Examples of such fatty acids are caprylic, capric, lauric, myristic, myristoleic, palmitic, palmitoleic, stearic, oleic, ricinoleic, linoleic, linolenic, eleostearic, arachidic, 20 behenic, and erucic. The fatty acids can be derived from suitable naturally occurring or synthetic fatty acids and can be saturated or unsaturated, including positional and geomPtric isomers. The fat materials of this invention are mixed esters of fatty acids, rather than esters of a single 25 type of fatty acid.
~ atty acids per se or nflturally occurring fats and oils can serve as the source for the fatty acid component in the sugar or sugar alcohol fatty acid ester. For example, rap0seed oil provides a good source for C22 fatty acid.
30 C16-C18 fatty acid can be provided by tallow, soybean oil, or cottonseed oil. Shorter chain fatty acids can be provided by coconut, palm kernel, or babassu oils. Corn oil, lard, olive oil, palm oil, peanut oil, safflower seed oil, sesame seed oil, and sunflower seed oil, are examples of other natural oils 35 which can serve as the source of the fatty acid component.
3~
The sugar or sugar alcohol fatty acid polyesters suitable for use herein can be prepared by a variety of methods well known to those skilled in the art. These method include:
transesterification of the sugar or sugar alcohol with methyl, S ethyl or glycerol fatty acid esters using a variety of catalysts; acylation of the sugar or sugar alcohol with a fatty acid chloride; acylation of the sugar or sugar alcohol with a fatty acid anhydride; and acylation of the sugar or sugar alcohol with a fatty acid, per se. As an example, the 10 preparation of sugar and sugar alcohol fatty acid esters is described in U.S. Pat. No. 2,831,854.
A characterizing feature of the sugar or sugar alcohol fatty acid polyesters useful in this invention is that they predominantly contain at least 4 fatty acid polyester groups.
15 Sugar or sugar alcohol fatty acid polyester compounds that contain 3 or less fatty acid estèr groups are digested in the intestinal tract much in the manner as ordinary triglyceride fats, but sugar or sugar alcohol fatty acid polyester compounds that contain four or more fatty acid ester groups 20 are digested to a lesser extent and thus have the desired low calorie properties for use in this invention.
Highly preferred low calorie fat materials according to this invenffon are sucrose fatty acid polyesters. Preferred sucrose fatty acid polyesters have the majority of their 25 hydroxyl groups esteri'ded with fatty acids. Preferably at least about 80~, and most preferably at least about 95~, of the sucrose fatty ncid pol~resters are selected from the group consisting of octaesters, heptaesters and hexaesters, and mixtures thereo~. Preferably, no more than about 35% of the 30 esters are hexaesters or heptaesters, and at least about 6096 of the sucrose fatty acid polyesters are octaesters. Most preferably, at least about 70% of the polyesters are octaesters .
In order to provide the required physical properties, the 35 sucrose fatty acid polyesters of this invention are preferably esterified with particular kinds of fatty acids. Preferably, at ~2~3~
least about 80~, and most preferably at least about 90~, of the fatty acids are selected from the group consistin~ of mixtures of palmitic, stearic, oleic, linoleic, and behenic acids .
More specifically, the following is a preferred fatty acid composition: from about 9% to about 12~ palmitic; from about 35% to about 53% stearic; from about 19% to about 43% oleic;
from about 2% to about 17% linoleic; from about 0% to about 2g6 linolenic; from about 0% to about 2P~ arachidic; from about 0%
to about 10% behenic; and from about 0% to about 2~ erucic.
The fo~owing fatty acid composition is most preferred:
from about 9~ to about 12~ palmitic; from about 42% to about 53% stearic; from about 19% to about 39% oleic; from about 2%
to about 17% linoleic; from about 0% to about 2% linolenic; from L5 about 0% to about 2% arachidic; from about 0% to about 10%
behenic; and from about 0% to about 2% erucic.
Polyglycerol fatty acid polyesters can also be low calorie fat materials of the present invention. Polyglycerol is prepared by the polymerization of glycerine in the presence of either acid or base. The polyglycerols can contain from 2 to 20 glycerol moieties. Preferably, the polyglycerols will be those having from 2 to 15 glycerol moieties.
The polyglycerol compounds can be made by any synthetic method . S ee, for example, U . S . 3, 9 68 ,169 to 2 5 Seiden and Martin ( 1976 ) . Esterification of the polyglycerols can also be done by any method known to the art, providing the resulting polyglycerol esters have the rheological properties required of the present invention.
Anlmal s tudies have now shown polyglycerol esters with 3 0 the eollowin~ rheological properties to be very effective at eliminating laxative side efeect: ta) a viscosity of 3.13 poise at a shear rate of 800 seconds 1, a viscosity of 5.18 poise at a shear rate of 100 seconds 1, and a viscosity of 32.43 poise at a shear rate of 10 seconds 1; (b) a thixotropic area of 3s 0.246 x 106 dynes/cm2-sec.; and (c) a liquid/solid stability of 53 . 45% .
3~3 Th~ "polycarboxylic acids esterified with fatty alcohols"
are tricarboxylic and tetracarboxylic acids and higher. The polycarbo~cylic acids can be partially or wholl3r esterified with fatty alcohols. At least three fatty alcohol ester groups must be on an acid molecule to make it partially nondigestible.
B. Methods for Making the Fat Materials Better Tasting While the fat materials of this invention offer an improvement in non-waxy taste when used alone in a food product, this invention relates to methods for making the fat substitutes even better-tasting than they are alone.
One method involves the use of an edible, absorbable, digestible food material which acts as a solvent for the fat substitute. It was discovered that by the addition of a food material such as a liquid triglyceride to the fat materials, the melting point of the materials is lowered, so that at mouth temperature (92F, 33.3C) the fat materials have a Solid Fat Content less than about 20~. Hence, when the fat materials are ingested they do not taste waxy in the mouth. After being ingested, the food material that acts as a solvent is 2 digested in the stomach and intestines, and the melting point reduction effect is thereby eliminated. The fat materials revert to their original solids content in the gastrointestinal tract. When the fat materials pass from the colon, then, they are viscous and stable enough to not cause a laxative side 2 5 effect .
Therefore, one aspect of the present invention is a composition of matter having a Solid Fat Content less than about 20% at mouth temperature (92F, 33.3C), comprising:
(a) an edible, wholly or partially nondigestible low calorie fat material having, at 100F (37.8C): (i) a viscosity of at least about 2 . 5 poise at a shear rate of 800 seconds 1, a viscosity of at least about ~ . 0 poise at a shear rate of 100 seconds 1, ancl a viscosity of at least about 25 . O poise at a shear rate of 10 seconds 1; (ii) a yield point of at least about 2,500 dynes/cm2; (iii) a thixotropic area of at least about 0.20 x 106 dynes/cm~-sec; and (iv) a liquid/solid stability of 3~
at least about 50%; and (b) an edible, absorbable, digestible food material which acts as a solvent for said fat substitute.
For very good non-waxy taste in the mouth, it is preferable that the composition have a Solid Fat Content less than about 10% at mouth temperature (92F, 33.3C), and most preferably less than about 5%.
The edible, absorbable, digestible food material which acts as a solvent for the fat substitute is preferably selected from the group consisting of triglycerides, monoglycerides, diglycerides, substituted mono- and diglycerides, polyglycerol esters, citrus oils, flavorants, edihle alcohols, edible food emulsifiers, and mixtures thereof. Most preferably, the food material is selected from the group consisting of triglycerides and substituted mono- and diglycerides, and mixtures thereof. By "substituted" mono- and diglycerides is meant mono- and diglycerides in which the free hydroxyl groups are substituted with edible short chain fatty acids , i. e., C2 through C8.
Edible food emulsifiers include mono- and diglycerides, lower sucrose esters (C1- C4), and lower polyglycerol esters (C -C ) The digestible food material must be capable of lowering the melting point ( freezing point) of the fat materials .
Freezing point depression generally follows the formula: I/T
= I/To ~ (R In x/delta Hf)~ where T = treezing point, To =
pure freezing point, X = mole fraction, and delta Hf = heat of fusion .
The amount and type Oe digestible food material usad as a solvent will depend on the end food product ln which the composition of this invention will be used. For example, a preferred food material for this purpose is triglycerides. In a margarine prodllct what is desired is a low Solid Fat Content and a fairly low viscosity. There is an optimum visco~ity so that the margarine is thin enough so that the saliva in the mouth can act on it and make it invert. If the margarine is too thin, it will disperse in the mouth before the P9~
saliva is able to act on it. As another example, shortening must have substantial plasticity because of its use in the areas of frying and baking. Yet, the shortening should not be so ~lrm as to taste very firm in the mouth. In summary, 5 a specific triglyceride or other food material is picked depending on the food product in which it will be used.
I t has been discovered that particular raffos of triglyceride and fat substitute (in particular sucrose polyesters) are desirable in terms of calorie reduction. To 10 maximize the calorie reduction benefit, from about 67~ to about 90% of the sucrose polyester is combined with from about 33% to about 10~ triglyceride. To obtain the minimum reduced calorie benefit that is allowed by current Government re gulations, from about 33% to about 90% sucrose polyester is combined with from about 66~6 to about 10% triglyceride.
The other method of this invention, for making the low calorie fat materials even more palatable, comprises ad~ing to the fat materials an edible, digesffble food emulsifier capable of forming an oil-in-water emulsion with the fat materials in 20 the mouth. Saliva from the mouth and any water in the food comprises the water portion of the emulsion, while the present fat material and any oil from the food comprises the oil part.
When the fat material is made into an oil-in-water emulsion with saliva, it does not taste waxy in the mouth. After 25 ingesffon, the food emulsifier is digested whi~e the fat material remains undigested, so the ~at material reverts tc. its original form. A good-tasting food product can be made that does not produce a laxative side effect.
Tendency of an emulsifier to form an oil-in-water 3~ emulsion is measured by its hydrophilic/lipophilic balance (HLB). The ernulsifler used in the composition of this invention must have an HL~3 value of at least 2.
Preferred food emulsifiers for use herein are selected from the group consisting of mono- and diglycerides, lower 35 sucrose esters, lower polyglycerol esters, and mixtures thereof .
3~
The compositions of the present invention can be used as a partial or total replacement for normdl triglyceride fat in any fat-containing food composition to provide low calorie benefits. In order to obtain a significant low calorie effect, 5 it is necessary that at least about 10% of the fat in the food composition comprises the present compositions. On the other hand, very low calorie and thus highly desirable food compositions of the invention are obtained when the fat comprises up to about 100% of the composiffons of this 10 invention. Hence, the compositions of the present invention can be used as a parffal or complete replacement for normal triglyceride fat in a salad or cooking oil, or a plastic shortening, or the like. The compositions can also be used as a partial or complete replacement for normal triglyceride 15 fat in fat-containing food products such as mayonnaise, margarine, and dairy products.
.~
, ~Z9~'~3~3 Analytical Methods I. Rheolo~y Measurements A. Sample Preparation The low calorie fat material is melted in a microwave oven at about 150F (66~C) to about 170F (77C). This takes approximately 2 minutes. The melted fat material is held at 100F + 5F (37.8C + 3C), and a 3 gram sample is weighed into a SoloR plastic souffle cup. The sample is then allowed to recrystallize at 100F + 5F (37.8C + 3C) for 24 hours. After the 24 hour time period has elapsed, the sample is taken to the viscometer in an insulated cup and the viscosity is measured.
B. Ferranti-Shirley Viscometer Operation Procedure A Ferranti-Shirley viscometer is used for the viscosity, yield point, and thixotropic area measurements. A cone is put into place, and the viscometer temperature is adjusted to 100F (37.8C). The chart recorder is calibrated, and the gap between the cone and plate is set. The cone speed is checked, and the cone and plate temperatures are equilibrated to 100F (37.8C). The panel controls are set. Sufficient sample is placed between the plate and the cone so that the gap is completely filled. The temperature is allowed to stabilize at 100F (37.8C) for about 30 seconds, and then the cone rotation and recording are started. A rheogram for the fat material is recorded and analyzed to determine the viscosity, yield point, and thixotropic area. Viscosity is measured at shear ratcs of 800 seconds 1, 100 seconds 1, and 10 séconds .
II. LiquidtSolid Stability Messurement 3 The sample is heated until it completely melts and is thoroughly mixed. The sample is then poured into centrifuge tubes at 100F + 5F. The samples then are allowed to recrystallize for 24 hours at 10QF + 5F. The samples are then centrifuged at 50,000 rpm for one hour at 37C. The percent liquid separated is then measured by comparing the relative heights of the liquid and solid phases.
.?~ 4L38 III. Solid Fat Content Measurement Before determining SFC values, the fat material sample is heated to a temperature of 158F (70C3 or higher for at least O . S hours or until the sample is completely melted . The 5 melted sample is then tempered at a temperature of 40F
(4.4C~ for at least 72 hours. After tempering, the SFC
value of the fat material at a temperature of 100F ~37.8C) i8 determined by pulsed nuclear magneffc resonance (PNMR3.
The method for determining SFC values of a fat by PNMR is 1 0 described in Madison and Hill , J . Amer . Oil . Chem . Soc ., Vol. 55 (1978), pp. 328-31.
The following Examples are intended to be further illustrative but not limiting of the present invenffon.
Example 1 Methyl esters of a fully hydrogenated soy oil and a partially hydrogenated soy oil, blended in a 45/55 ratio (227.3 kg), and 36 kg. of an 18 wt. percent solu~on of potassium hydroxide in methanol are mixed in a stainless steel batch reactor. This mixture is then heated to 122F (50C) with 20 a~itation for 1 to 2 hours at atmospheric pressure. During this time, a portion of the methyl esters are saponified. A
vacuum is then pu~led on the system to remove the last traces of methanol.
Granular sucrose (95.5 kg.) is added to the soap/ester 25 mixture to give a 5 :1 molar ratio of ester to sucrose.
Potassium carbonate is then add~d to the mixture (approx.
0 . 5 wt . percent of the reaction mix) to catalyze the transesterificaffon. This mixture is agitated and heated under vacuum at about 275F (135C) for up to 8 hours to 30 form the mono-, di- and trisucrose esters. Small quantities OI tetrn- and pentaesters are also formed during this stage.
Additional methyl ester (276.7 kg) which has been preheated to 275F (135C) is added to bring and malntain the molar ratio of the esters to sucrose to 12 :1. When the reaction 1~. '.
3~3 conditions stabilize at 275F (135C), a nitrogen sparge is used to improve agitation and promote methanol StFipping. As the r~action occurs, the reaction mixture becomes viscous and then thins out. This second reaction stage lasts s approximately 24 to 36 hours.
After the reac1ion mixture h~s become thin, it is cooled to between 149F (65C) and 185F (85C). The crude reaction mixture is agitated with a dilute solution of methanol, sodium chloride and water. The volume of thi~ wash solution is equal to 20% to 40% of the reaction mixture volume. The mixed phases are then allowed to settle for approximately 3 0 to 60 minutes. The lower settled phase which cont~ins the soaps, excess sugars and methanol i8 drawn off and discarded. The upper settled phase which comprises the rafined sucrose polyesters is washed again. Usually 2 to 4 washes are used.
The sucrose polyesters are then washed with a 1~ glacial acetic acid in water solution at 10% to 20% of the volume of the reaction mix. This is fo~owed by water wash of the same 2 0 volume .
The reaction mix is then dried to remo~re moisture at 176F (80C) under 10 mm Hg or less vacuum for 30 to 60 minutes . Filtrol 10~( 0 . 5 wt . percent), and a filter aid ( 0 . 5 wt. percent) are added and the mix is agitated at 167F
(75C) to 185F (85C). The slurry is separated by filtra'don or other mean~ until there is less than 0.1 wt. percent fines.
The li~uid is then passed through a 1 micromillimeter filter.
The refined and bleached reaction mix is then returned to the stainless steel batch reactor to distill off the buhlc of the methyl esters. The distilla'don takes place at 374F
(190C) to 482F (250C) under approximately 5 mm Hg of vacuum. This step is complste when it is visually evident that the distillation has slowed down.
The ~ucrose polyester is then deodorized in a stainless steel batch deodorizer or other suitable device at 374F
(19ûC) to 482F (250C) under a vacuum of about 5 mm Hg 3~
-zo-with steam sparging. Deodori~ation is continued until the methyl ester content is helow 200 ppm. The deodorizer contents are then cooled while using inert gas sparging.
After cooling to 149F (65C), the deodorizer is brought to atmospheric pressure. The sucrose polyester is stored in clean stainless stesl drums.
This produces a sucrose polyester product having the fatty acid composition specified in Table I. Rheology and effectiveness at preventing laxative side effect are listed in 1~ Table 2.
Example 2 Methyl esters of a fully hydrogenated soy oil and a touch hardened soy oil, blended in a 55/45 ratio (16 kg), and 2 kg. of an 15 wt. percent solution of potassium hydroxide in methanol are mixed in a stainless steel batch reactor. This mixture is then heated to 86F (30C) with agitation for 1 to 2 hours at atmospheric pressure. During this time, a portion of the methyl esters are saponified. A vacuum is then pulled on the system to remove the last traces of methanol.
Powdered sucrose (3 kg.) is added to the soap/ester mixture to give a 6 :1 molar ratio of ester to sucrose.
Potassium carbonate is then added to the mixture ( approx .
0 . 5 wt . percent of the reactlon mix) to catalyze the transesterification. This mixture is agitated and heated under vacuum at about 275F (135C) ~or up to 2-1/2 hours to form the mono-, di- and trisucrose esters. Small quantities of tetra- and pentaesters are also formed during this stage. Additional methyl ester (19.5 kg) which has been preheated to 275F (135C) is added to bring and maintain the molar ratio of the esters to sucrose to 12:1. When the reaction conditions stabilize at 275F (135C), a nitrogen sparge is used to improve a~itation and promote methanol stripping. As the reaction occurs, the reaction mixture becomes viscous and then thins out. This second reaction stage lasts approximately 4 to 8 hours.
After the reaction mixture has become thin, it is cooled to between 149F (65C) and 185F (85C). The crude reaction mixture is agitated with a dilute solution of methanol~
sodi~m chloride and water. The volume of this wash solution is equal to 20Q6 to 40% of the reaction mixture volume. The mixed phases are then allowed to settle for approximately 3 0 to 60 minutes. The lower settled phaqe which contains the soaps, excess sugars and methanol is drawn off and discarded. The upper settled phase which comprise~ the 1 Q refined sucrose polyesters is washed again . Usua~ly 2 to 4 washes are used.
The sucrose polyesters are then washed with a 1% glacial acetic acid in water solution at 10% to 20% of the ~rolume of the reaction mix. This is followed by water wash of the same volume.
The reaction mix is then dried to remove moisture at 176F (80C) under 10 mm Hg or less vacuum for 30 to 60 minutes. Filtrol 105 (0.5 wt. percent), and a filter aid (0.5 wt. percent) are added and the mix is agitated at 167F
(75C) to 185F (85C). The slurry is separated by filtration or other means until there is less than 0.1 wt. percent fines.
The liquid is then passed through a 1 micromillimeter filter.
The refined and bleached reaction mix is put into a stainless steel batch deodorizer to distill off the bulk of the methyl esters. The distillation takes place at 374F (190C) to 482F (250C) under approximately 5 mm Hg of vacuum.
This step is complete when it is visually evident that the distillation has slowed down.
The sucrose polyester is then deodorized in a stainless steel batch deodorizer or other suitable device at 374F
(190C) to 482F (250C) under a vacuum of about 5 mm Hg with steam sparging. Deodorlzation is continued until the methyl ester content is below 200 ppm. The deodorizer contents are then cooled while using inert gas sparging.
After cooling to 149F (65C), the deodorizer is brought to atmospheric pressure. The sucrose polyester is stored in clean stainless steel drums.
This produces a sucrose polyester product having the fatty acid composition specified in Table I. Rheology and 5 effectiveness at preventing laxative side effect are listed in Table II.
The results shown in Tables I and II i31ustrate that sucrose polyesters prepared accordin~ to Examples 1 and 2 have the properties of the low calorie fat materials of the 1 Q present invention . The third column in Table I shows the properties of a liquid sucrose polyester prepared according to a method known to the art, and not falling within the present invention .
Table II compares the rheology and effecffveness at 15 prevenffng laxative side effect of the three samples.
Examples 1 and 2 have rheological properties according to this invention; the liquid sucrose polyester does not. The liquid sucrose polyester results in a 15% oil loss when ingested. By contrast, the sucrose polyesters prepared in Examples 1 and 20 2 result in 0% oil loss, showing that they are very effective at eliminating laxative side effect.
When the sucrose polyesters of Examples 1 and 2 are mixed with triglyceride in a ratio of 75% sucrose polyester and 25% triglyceride, a composition is made that tastes very good 25 when ingested and that does not cause a laxative side efeect.
3~3 T able Sucrose Polyester Composition Liquid Sucrose Example 1Example 2Polyester Fatty Acid Composition % % %
Others 2.4 2.3 3.4 C 11.4 9.4 8.6 C16 44.0 50.8 5.7 10 C 8 37.2 20.4 45.6 c1~8.2 2.6 14.8 31.7 C 0.6 0.3 0.
c20 3 0.6 0.6 0.6 C22 1.2 1.4 0.0 15 I.V. 38.2 47.6 62.6 Ester Distribution % % 96 Octa 94.5 79.0 71.1 Hepta 5.6 19.2 24.0 Hexa 0.0 1.8 4.9 Penta 0.1 0.1 0.1 ~ Penta 0.1 0.1 0.1 SFC Profile % % %
F. 67.6 64.3 0 2570 F. 55.2 53.6 0 F. 44.2 43.0 0 92 F. 23.3 21.1 0 105 F. 5.2 2.7 0 98.6 F. 14.3 11.9 0 30 DSC Behavior C. C. C.
~ . . .. .... . _ .
Complete Melt Point38.9 42.5 -20.0 Maximum Melt Point36.0 39.4 -35.0 35 H eat of Fusion 14.8 11.7 10.6 -o~a R ¦ o ¢
~ C~
x ~ E X x ~a ~
l_ ~' ~ ~
O,~ _~
.
~ 3) o ''~
~ ~a ~ 0~O 0 0 ~
~i a
Claims (28)
1. A composition of matter having a Solid Fat Content less than about 20% at mouth temperature (92°F, 33.3°C), comprising:
(a) an edible, wholly or partially nondigestible low calorie fat material having, at 100°F (37.8°C):
(i) a viscosity of at least about 2.5 poise at a shear rate of 800 seconds-1, a viscosity of at least about 4.0 poise at a shear rate of 100 seconds-1, and a viscosity of at least about 25.0 poise at a shear rate of 10 seconds-1;
(ii) a yield point of at least about 2,500 dynes/cm2;
(iii) a thixotropic area of at least about 0.20 x 106 dynes/cm2-sec; and (iv) a liquid/solid stability of at least about 50%;
and (b) an edible, absorbable, digestible food material which acts as a solvent for said fat material.
(a) an edible, wholly or partially nondigestible low calorie fat material having, at 100°F (37.8°C):
(i) a viscosity of at least about 2.5 poise at a shear rate of 800 seconds-1, a viscosity of at least about 4.0 poise at a shear rate of 100 seconds-1, and a viscosity of at least about 25.0 poise at a shear rate of 10 seconds-1;
(ii) a yield point of at least about 2,500 dynes/cm2;
(iii) a thixotropic area of at least about 0.20 x 106 dynes/cm2-sec; and (iv) a liquid/solid stability of at least about 50%;
and (b) an edible, absorbable, digestible food material which acts as a solvent for said fat material.
2. A composition according to Claim 1 wherein the fat material is selected from the group consisting of polyol fatty acid polyesters and polycarboxylic acids esterified with fatty alcohols, and mixtures thereof.
3. A composition according to Claim 2 wherein the composition has a Solid Fat Content less than about 10% at mouth temperature (92°F, 33.3°C).
4. A composition according to Claim 3 wherein the composition has a Solid Fat Content less than about 5% at mouth temperature.
5. A composition according to Claim 2 wherein the digestible food material is a member selected from the group consisting of triglycerides, monoglycerides, diglycerides, substituted mono- and diglycerides, polyglycerol esters, citrus oils, flavorants, edible alcohols, edible food emulsifiers, and mixtures thereof.
6. A composition according to Claim 5 wherein the digestible food material is selected from the group consisting of triglycerides and edible food emulsifiers, and mixtures thereof.
7. A composition according to Claim 6 wherein the digestible food material is a triglyceride.
8. A composition according to Claim 7 wherein the composition comprises from about 33% to about 90% of the nondigestible fat material and from about 10% to about 66% of the triglyceride.
9. A composition according to Claim 8 wherein the composition comprises from about 67% to about 90% of the nondigestible fat material and from about 10% to about 33% of the triglyceride.
10. A composition according to Claim 2 wherein the fat material has a liquid/solid stability of at least about 90.
11. A composition according to Claim 2 wherein the fat material has a Solid Fat Content at 100°F (37.8°C) of at least about 5%.
12. A composition according to Claim 11 wherein the fat material has a Solid Fat Content of at least about 10%.
13. A composition according to Claim 2 wherein the fat material is selected from the group consisting of sugar fatty acid polyesters and sugar alcohol fatty acid polyesters, and mixtures thereof, the sugars and sugar alcohols containing from 4 to 8 hydroxyl groups and each fatty acid group having from about 8 to about 22 carbon atoms.
14. A composition according to Claim 13 wherein the fat material comprises sucrose fatty acid polyesters, and wherein at least about 60% of the polyesters are octaesters.
15. A composition according to Claim 14 wherein at least about 80% of the fatty acids are selected from the group consisting of palmitic, stearic, oleic, linoleic, and behenic acids, and mixtures thereof.
16. A low calorie fat-containing food composition comprising non-fat ingredients and fat ingredients, wherein from about 10% to about 100% of the total fat ingredients is a composition according to any of Claims 1, 2 or 3.
17. A composition of matter comprising:
(a) an edible, wholly or partially nondigestible low calorie fat material having, at 100°F (37.8°C):
(i) a viscosity of at least about 2.5 poise at a shear rate of 800 seconds-1, a viscosity of at least 4.0 poise at 100 seconds-1, and a viscosity of at least 25.0 poise at 10 seconds-1;
(ii) a yield point of at least about 2,500 dynes/cm2;
(iii) a thixotropic area of at least about 0.20 x 106 dynes/cm2-sec;
(iv) a liquid/solid stability of at least about 50%;
and (b) a food emulsifier capable of forming an oil-in-water emulsion with the low calorie fat material in the mouth.
(a) an edible, wholly or partially nondigestible low calorie fat material having, at 100°F (37.8°C):
(i) a viscosity of at least about 2.5 poise at a shear rate of 800 seconds-1, a viscosity of at least 4.0 poise at 100 seconds-1, and a viscosity of at least 25.0 poise at 10 seconds-1;
(ii) a yield point of at least about 2,500 dynes/cm2;
(iii) a thixotropic area of at least about 0.20 x 106 dynes/cm2-sec;
(iv) a liquid/solid stability of at least about 50%;
and (b) a food emulsifier capable of forming an oil-in-water emulsion with the low calorie fat material in the mouth.
18. A composition according to Claim 17 wherein the fat material is selected from the group consisting of polyol fatty acid polyesters and polycarboxylic acids esterified with fatty alcohols, and mixtures thereof.
19. A composition according to Claim 18 wherein the food emulsifier is selected from the group consisting of mono-and diglycerides, lower sucrose esters, lower polyglycerol esters, and mixtures thereof.
20. A composition according to Claim 18 wherein the polyol fatty acid polyesters are selected from the group consisting of sugar fatty acid polyesters and sugar alcohol fatty acid polyesters, and mixtures thereof.
21. A composition according to Claim 20 wherein the polyol fatty acid polyesters are sucrose fatty acid polyesters, and wherein at least about 60% of the polyesters are octaesters.
22. A composition according to Claim 21 wherein the fatty acids have the following composition: from about 9% to about 12% palmitic; from about 35% to about 53% stearic; from about 19% to about 43% oleic; from about 2% to about 17%
linoleic; from about 0% to about 2% linolenic; from about 0% to about 2% arachidic; and from about 0% to about 10% behenic.
linoleic; from about 0% to about 2% linolenic; from about 0% to about 2% arachidic; and from about 0% to about 10% behenic.
23. A low calorie fat-containing food composition comprising non-fat ingredients and fat ingredients, wherein from about 10% to about 100% of the total fat ingredients is a composition according to any of Claims 17, 18 or 19.
24. A low calorie fat-containing food composition comprising non-fat ingredients and fat ingredients, wherein from about 10% to about 100% of the total fat ingredients is a composition according to any of Claims 4, 5 or 6.
25. A low calorie fat-containing food composition comprising non-fat ingredients and fat ingredients, wherein from about 10% to about 100% of the total fat ingredients is a composition according to any of Claims 7, 8 or 9.
26. A low calorie fat-containing food composition comprising non-fat ingredients and fat ingredients, wherein from about 10% to about 100% of the total fat ingredients is a composition according to any of Claims 10, 11 or 12.
27. A low calorie fat-containing food composition comprising non-fat ingredients and fat ingredients, wherein from about 10% to about 100% of the total fat ingredients is a composition according to any of Claims 13, 14, or 15.
28. A low calorie fat-containing food composition comprising non-fat ingredients and fat ingredients, wherein from about 10% to about 100% of the total fat ingredients is a composition according to any of Claims 20, 21 or 22.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000530910A CA1299438C (en) | 1987-03-02 | 1987-03-02 | Method for making better tasting low calorie fat materials |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000530910A CA1299438C (en) | 1987-03-02 | 1987-03-02 | Method for making better tasting low calorie fat materials |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1299438C true CA1299438C (en) | 1992-04-28 |
Family
ID=4135077
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000530910A Expired - Lifetime CA1299438C (en) | 1987-03-02 | 1987-03-02 | Method for making better tasting low calorie fat materials |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1299438C (en) |
-
1987
- 1987-03-02 CA CA000530910A patent/CA1299438C/en not_active Expired - Lifetime
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