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WO2012168727A1 - Cristallisation de graisse de triglycérides - Google Patents

Cristallisation de graisse de triglycérides Download PDF

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Publication number
WO2012168727A1
WO2012168727A1 PCT/GB2012/051297 GB2012051297W WO2012168727A1 WO 2012168727 A1 WO2012168727 A1 WO 2012168727A1 GB 2012051297 W GB2012051297 W GB 2012051297W WO 2012168727 A1 WO2012168727 A1 WO 2012168727A1
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WIPO (PCT)
Prior art keywords
triglyceride
moringa
mono
glycerol
oil
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/GB2012/051297
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English (en)
Inventor
Paul Wassell
Mark Farmer
Stuart Andrew WARNER
Allan Torben Bech
Niall W. G. YOUNG
Graham BONWICK
Christopher Smith
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International N&H Denmark ApS
Original Assignee
DuPont Nutrition Biosciences ApS
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Publication date
Priority claimed from GBGB1109649.2A external-priority patent/GB201109649D0/en
Priority claimed from GBGB1117039.6A external-priority patent/GB201117039D0/en
Application filed by DuPont Nutrition Biosciences ApS filed Critical DuPont Nutrition Biosciences ApS
Publication of WO2012168727A1 publication Critical patent/WO2012168727A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B15/00—Solidifying fatty oils, fats, or waxes by physical processes
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/01—Other fatty acid esters, e.g. phosphatides
    • A23D7/011—Compositions other than spreads
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings or cooking oils characterised by ingredients other than fatty acid triglycerides
    • A23D9/013—Other fatty acid esters, e.g. phosphatides

Definitions

  • the present invention relates to a process.
  • the present invention relates to a process for controlling the crystallisation of a triglyceride.
  • the improvement can be form example to accelerate or enhance the crystallisation of a triglyceride or, if desired, to retard the crystallisation of a triglyceride.
  • fats are often heated to elevated temperatures to allow for ease of processing, for example to allow for them to become liquid.
  • These fats which are either at room or elevated temperatures may often require cooling and this is typically performed under accelerated conditions to minimise the processing time of the food product and to therefore minimise processing costs.
  • cooling rates of 5° C, 10° C, 20° C or 35° C per minute are not unusual. These cooling rates contrast with the more usual rate of 1 ° C per minute used in the scientific investigation of fat crystallisation.
  • These forced cooling rates of processing apparatus can often result in undesirable fat characteristics.
  • the degree, extent and/or type of fat crystallisation may be sub optimal. This may be to the detriment of the properties of the final food product.
  • additives which may act in a number of ways.
  • additives are provided which lower the onset temperature of fat crystallisation. This allows for rapid cooling of the food product close to the desired temperature before the fat crystallisation temperature is reached and the problems of rapid crystallisation are encountered.
  • Materials such as polyglycerol polyricinoleic acid (PGPR) may be used to decrease the onset temperature of fat crystallisation.
  • PGPR polyglycerol polyricinoleic acid
  • An additional or alternative approach is to provide a material which may act as a nucleating medium. Such a nucleation material allows for a more structured recrystallisation of the fat. Which approach is chosen or whether both approaches are chosen will depend on the fat blend and the cooling profile to be used.
  • a yet further or alternative approach is to provide an additive material which stabilises the fat crystallisation process and therefore allows for rapid crystallisation resultant from the rapid cooling while maintaining the fat characteristics which would have been observed from a slower cooling of the fat.
  • the present invention provides a process for controlling the crystallisation of a triglyceride, the process comprising the steps of
  • the present invention provides use of a mono or di ester of glycerol and Moringa oi! to control the crystallisation of a triglyceride.
  • the present invention provides use of a mono or di ester of glycerol and Moringa oil to increase onset temperature of crystallisation of a triglyceride compared to the triglyceride in the absence of the mono or di ester of glycerol and Moringa oil.
  • control crystallisation' or 'controlling crystallisation' it is meant that the rate or degree of crystallisation of the triglyceride can be increased or retarded.
  • the terms 'control crystallisation' or 'controlling crystallisation' encompass increasing the rate of crystallisation, increasing the extent of crystallisation, decreasing the rate of crystallisation and decreasing the extent of crystallisation.
  • Moringa mono and di glycerides may in some aspects be used to increase the rate of crystallisation and/or increase the extent of crystallisation of triglycerides.
  • Moringa mono and di glycerides may in some aspects be used to decrease the rate of crystallisation and/or decrease the extent of crystallisation of triglycerides.
  • the mono or di ester of glycerol and Moringa oil is particularly advantageous as a source of oil to prepare the mono and di glycerides because the plant has been known as a source of edible materials for many years. Therefore the oil obtained from the plant may be regarded as safe for consumption.
  • the use of mono and di glycerides prepared from Moringa oil for controlling crystallisation of a triglyceride has not previously been taught.
  • Moringa is the sole genus in the flowering plant family Moringaceae.
  • the 13 species it contains are from tropical and subtropical climates and range in size from tiny herbs to very large trees. Moringa may therefore be grown in many climates in which cash crops may not currently be cultivated. Moringa cultivation is promoted as a means to combat poverty and malnutrition and the plant grows quickly in many types of environments.
  • Moringa species are drought-resistant and can grow in a wide variety of poor soils, even barren ground, with soil pH between 4.5 and 9.0.
  • the present invention provides a process for improving the crystallisation of a triglyceride, the process comprising the steps of (i) providing a triglyceride (ii) contacting the triglyceride with a mono or di ester of glycerol and Moringa oil.
  • Moringaceae has more than 13 species (Verdcourt 1985), of which two species viz. M. oleifera Lam. (syn. M. pterygosperma Gaertn.) and M. concanensis Nimmo occur in India.
  • M. oleifera (the drumstick tree, horse radish tree, West Indian Ben) is a fast-growing, medium sized and drought-resistant tree distributed in the sub-Himalayan tracts of northern India (Singh et al. 2000; Hsu et al. 2006).
  • the species of Moringa are further discussed in Bennet, R. ., Mellon, F.A., Foidl, N., Pratt, J.H., DuPont, M.S., Perkins, L.,and roon, P.A.
  • M oleifera locally called shobhanjana, murungai, soanjna, shajna, sainjna
  • shobhanjana murungai, soanjna, shajna, sainjna
  • Moringa arborea Verde. (Kenya), Moringa borziana Mattel, Moringa concanensis Nimmo, Moringa drouhardii Jum. - Bottle Tree (southwestern Madagascar), Moringa hildebrandtii Engl. - Hildebrandt's Moringa (southwestern Madagascar), Moringa longituba Engl., Moringa oleifera Lam. (syn. M.
  • the Moringa is a plant of the species Moringa oleifera. iWono or Di Ester Of Glycerol And Moringa Oil
  • Mono- and diglycerides are generally produced by interesterification (glycerolysis) of triglycerides with glycerol, see fig. below: CaOCOR j CH 2 OH
  • Triglycerides react with glycerol at high temperaiure (200-250°C) under alkaline conditions, yielding a mixture of monoglycerides, diglycerides and triglycerides as well as unreacted glycerol.
  • the content of monoglycerides vary typically from 10-60% depending on the glycerol/fat ratio.
  • mono- and diglycerides may also be prepared via direct esterification of glycerol with a fatty acid mixture.
  • glycerol is removed from the mixture above by e.g. distillation, the resulting mixture of monoglycerides, diglycerides and triglycerides is often sold as a "mono-diglyceride" and used as such. Distilled monoglyceride may be separated from the mono-diglyceride by molecular or short path distillation .
  • the mono or di ester of glycerol and Moringa oil may be contacted with the triglyceride in the desired amount to achieve the desired function of the mono or di ester of glycerol and Moringa oil, namely to control crystallisation. !n one embodiment, mono or di ester of glycerol and Moringa oil is contacted with the triglyceride in an amount of at least about 0.01 % w/w based on the total weight of the triglyceride.
  • mono or di ester of glycerol and Moringa oil is contacted with the triglyceride in an amount of at least about 0.02% w/w based on the total weight of the triglyceride, !n one embodiment, mono or di ester of glycerol and Moringa oil is contacted with the triglyceride in an amount of at least about 0.03% w/w based on the total weight of the triglyceride. In one embodiment, mono or di ester of glycerol and Moringa oil is contacted with the triglyceride in an amount of at least about 0.04% w/w based on the total weight of the triglyceride.
  • mono or di ester of glycerol and Moringa oil is contacted with the triglyceride in an amount of at least about 0.05% w/w based on the total weight of the triglyceride. In one embodiment, mono or di ester of glycerol and Moringa oil is contacted with the triglyceride in an amount of at [east about 0.075% w/w based on the total weight of the triglyceride. In one embodiment, mono or di ester of glycerol and Moringa oil is contacted with the triglyceride in an amount of at least about 0.1 % w/w based on the total weight of the triglyceride.
  • mono or di ester of glycerol and Moringa oil is contacted with the triglyceride in an amount of at least about 0.15% w/w based on the total weight of the triglyceride. In one embodiment, mono or di ester of glycerol and Moringa oil is contacted with the triglyceride in an amount of at least about 0.2% w/w based on the total weight of the triglyceride. In one embodiment, mono or di ester of glycerol and Moringa oil is contacted with the triglyceride in an amount of at least about 0.3% w/w based on the total weight of the triglyceride.
  • mono or di ester of glycerol and Moringa oil is contacted with the triglyceride in an amount of at least about 0.4% w/w based on the total weight of the triglyceride. In one embodiment, mono or di ester of glycerol and Moringa oil is contacted with the triglyceride in an amount of at least about 0.5% w/w based on the total weight of the triglyceride. In one embodiment, mono or di ester of glycerol and Moringa oil is contacted with the triglyceride in an amount of at least about 1.0% w/w based on the total weight of the triglyceride.
  • mono or di ester of glycerol and Moringa oil is contacted with the triglyceride in an amount of at least about 2.0% w/w based on the total weight of the triglyceride. In one embodiment, mono or di ester of glycerol and Moringa oil is contacted with the triglyceride in an amount of at least about 3.0% w/w based on the total weight of the triglyceride. In one embodiment, mono or di ester of glycerol and Moringa oil is contacted with the triglyceride in an amount of at least about 5.0% w/w based on the total weight of the triglyceride. In one embodiment, mono or di ester of glycerol and Moringa oil is contacted with the trig!yceride in an amount of at least about 10.0% w/w based on the total weight of the triglyceride.
  • mono or di ester of glycerol and Moringa oil is contacted with the triglyceride in an amount of from about 0.01 to about 2.0% w/w based on the total weight of the triglyceride. In one embodiment, mono or di ester of glycerol and Moringa oil is contacted with the triglyceride in an amount of from about 0.01 to about 1.8% w/w based on the total weight of the triglyceride. In one embodiment, mono or di ester of glycerol and Moringa oil is contacted with the triglyceride in an amount of from about 0.01 to about 1.5% w/w based on the total weight of the triglyceride.
  • mono or di ester of giycerol and Moringa oil is contacted with the triglyceride in an amount of from about 0.05 to about 1.5% w/w based on the total weight of the triglyceride. In one embodiment, mono or di ester of glycerol and Moringa oil is contacted with the triglyceride in an amount of from about 0.075 to about 1.5% w/w based on the total weight of the triglyceride. In one embodiment, mono or di ester of glycerol and Moringa oil is contacted with the triglyceride in an amount of from about 0.1 to about 1.5% w/w based on the total weight of the triglyceride.
  • mono or di ester of glycerol and Moringa oil is contacted with the triglyceride in an amount of from about 0.1 to about 1.2% w/w based on the total weight of the triglyceride. In one embodiment, mono or di ester of glycerol and Moringa oil is contacted with the triglyceride in an amount of from about 0.1 to about 1.0% w/w based on the total weight of the triglyceride. In one embodiment, mono or di ester of glycerol and Moringa oil is contacted with the triglyceride in an amount of from about 0.1 to about 0.8% w/w based on the total weight of the triglyceride.
  • mono or di ester of glycerol and Moringa oil is contacted with the triglyceride in an amount of from about 0.1 to about 0.6% w/w based on the total weight of the triglyceride. In one embodiment, mono or di ester of glycerol and Moringa oil is contacted with the triglyceride in an amount of from about 0.2 to about 0.6% w/w based on the total weight of the triglyceride. In one embodiment, mono or di ester of glycerol and Moringa oil is contacted with the triglyceride in an amount of from about 0.3 to about 0.6% w/w based on the total weight of the triglyceride.
  • mono or di ester of glycerol and Moringa oil is contacted with the triglyceride in an amount of no greater than 2.0wt% based on the triglyceride. In one embodiment, mono or di ester of glycerol and Moringa oil is contacted with the triglyceride in an amount of from 0.5 to 1.0 wt% based on the triglyceride.
  • the present invention provides a use of a mono or di ester of glycerol and Moringa oil.
  • a mono or di ester of glycerol and Moringa oil to increase onset temperature of crystallisation of a triglyceride compared to the triglyceride in the absence of the mono or di ester of glycerol and Moringa oil.
  • the mono or di ester of glycerol and Moringa oil may be contacted with triglyceride in any suitable means,
  • the triglyceride is part of or may be incorporated into an emulsion.
  • a suitable emulsion includes an oil in water emulsion or a water in oil emulsion.
  • the mono or di ester of glycerol and Moringa oil may be contacted with the triglyceride by any suitable route. It will be appreciated that in such an emulsion, the triglyceride will constitute a fat phase of the emulsion.
  • the mono or di ester of glycerol and Moringa oil may be added to one or both of the (i) fat phase; and (ii) aqueous phase prior to the contact of the (i) fat phase; and (ii) aqueous phase and thereby be present on contact of the (i) fat phase; and (ii) aqueous phase.
  • the mono or di ester of glycerol and Moringa oil may be added to the (i) fat phase; and (ii) aqueous phase once they have been combined or as they are combined.
  • the present process and use further comprises contacting the triglyceride with polyglycerol polyricinoleic acid (PGPR).
  • PGPR polyglycerol polyricinoleic acid
  • the contact with the PGPR may be prior to, subsequent to or simultaneously with the contact of the triglyceride with the mono or di ester of glycerol and Moringa oil.
  • the present inventors have further identified that the presence of a monoglyceride of a saturated C16 to C26 fatty acid may assist in the achievement of the desired function of the mono or di ester of glycerol and Moringa oil, namely to control crystallisation.
  • the present invention further provides * a process for controlling the crystallisation of a triglyceride, the process comprising the steps of
  • the saturated fatty acid of the monoglyceride may have a carbon chain length of from 16 to 26 carbon atoms. In one aspect the saturated fatty acid of the monoglyceride may have a carbon chain length of from 16 to 24 carbon atoms. In one aspect the saturated fatty acid of the monoglyceride may have a carbon chain length of from 16 to 22 carbon atoms. In one aspect the saturated fatty acid of the monoglyceride may have a carbon chain length of from 18 to 22 carbon atoms. In one aspect the saturated fatty acid is C16 saturated fatty acid. In one aspect the saturated fatty acid is C18 saturated fatty acid. In one aspect the saturated fatty acid is C20 saturated fatty acid. In one aspect the saturated fatty acid is C22 saturated fatty acid. In one aspect the saturated fatty acid is C24 saturated fatty acid. In one aspect the saturated fatty acid is C26 saturated fatty acid.
  • the saturated fatty acid of the monoglyceride has a carbon chain length of from 18 to 22 carbon atoms.
  • the saturated fatty acid of the monoglyceride has a carbon chain length of 18 carbon atoms.
  • the saturated fatty acid of the monoglyceride has a carbon chain length of 22 carbon atoms.
  • the monoglyceride of a saturated C16 to C26 fatty acid is present in the dispersion in an amount of at least about 0.01 % w/w based on the total weight of the dispersion. In one embodiment, the monoglyceride of a saturated C16 to C26 fatty acid is present in the dispersion in an amount of at least about 0.02% w/w based on the total weight of the dispersion. In one embodiment, the monoglyceride of a saturated C16 to C26 fatty acid is present in the dispersion in an amount of at least about 0.05% w/w based on the total weight of the dispersion.
  • the monoglyceride of a saturated C16 to C26 fatty acid is present in the dispersion in an amount of at ieast about 0.1 % w/w based on the total weight of the dispersion. In one embodiment, the monoglyceride of a saturated C16 to C26 fatty acid is present in the dispersion in an amount of at Ieast about 0.2% w/w based on the total weight of the dispersion. In one embodiment, the monoglyceride of a saturated C16 to C26 fatty acid is present in the dispersion in an amount of at Ieast about 0.5% w/w based on the total weight of the dispersion.
  • the monoglyceride of a saturated C16 to C26 fatty acid is present in the dispersion in an amount of at least about 1.0% w/w based on the total weight of the dispersion. In one embodiment, the monoglyceride of a saturated C16 to C26 fatty acid is present in the dispersion in an amount of at least about 2.0% w/w based on the total weight of the dispersion. In one embodiment, the monoglyceride of a saturated C16 to C26 fatty acid is present in the dispersion in an amount of at Ieast about 3.0% w/w based on the total weight of the dispersion.
  • the monoglyceride of a saturated C16 to C26 fatty acid is present in the dispersion in an amount of at Ieast about 5.0% w/w based on the total weight of the dispersion. In one embodiment, the monoglyceride of a saturated C16 to C26 fatty acid is present in the dispersion in an amount of at Ieast about 10.0% w/w based on the total weight of the dispersion.
  • Polyglycerols are substances consisting of oligomer ethers of glycerol. Polyglycerols are usually prepared from an alkaline polymerisation of glycerol at elevated temperatures.
  • polyglycerol is typically a mixture of polyglycerols of varying degrees of polymerisation.
  • the polyglycerol used to form the polyglycerol ester of a polymerised fatty acid is a mixture of polyglycerols selected from diglycerol, triglycerol, tetraglycerol, pentaglycerol, hexaglycerol, heptaglycerol, octaglycerol, nonaglycerol and decaglycerol.
  • triglycerol is the most abundant polyglycerol in the mixture of polyglycerols.
  • tetraglycerol is the most abundant polyglycerol in the mixture of polyglycerols.
  • the mixture of polyglycerols contains triglycerol in an amount of 30-50 wt% based on the total weight of polyglycerols and contains tetraglycerol in an amount of 10-30 wt% based on the total weight of polyglycerols.
  • the polyglycerol is considered to be a diglycerol.
  • the polyglycerol is considered to be a triglycerol.
  • the polyglycerol is considered to be a tetraglycerol.
  • the polyglycerol is considered to be a pentaglycerol. In one embodiment, the polyglycerol is considered to be a hexaglycerol. In one embodiment, the polyglycerol is considered to be a heptaglycerol. In one embodiment, the polyglycerol is considered to be an octaglycerol. In one embodiment, the polyglyceroi is considered to be a nonaglycero!. !n one embodiment, the polyglyceroi is considered to be a decaglycerol.
  • the polyglyceroi is considered to be a triglycerol.
  • the polyglycero! is considered to be a tetraglyeerol.
  • the polyglyceroi moiety shall be composed of not less than 75% of di-, tn - and tetraglycerols and shall contain not more than 10% of polyglycerols equal to or higher than heptaglyceroi.
  • Polyglycerols may be linear, branched or cyclic in structure. Typically, all three types of polyglyceroi structure are present in the composition of the present invention.
  • Fatty acids are well known in the art. They typically comprise an “acid moiety” and a "fatty chain". The properties of the fatty acid can vary depending on the length of the fatty chain, its degree of saturation, and the presence of any substituents on the fatty chain. Examples of fatty acids are palmitic acid, stearic acid, oleic acid, and ricinoleic acid.
  • the fatty acid used according to this aspect of the present invention is ricinoleic acid.
  • Ricinoleic acid is a chiral molecule. Two steric representations of ricinoleic acid are given below:
  • Ricinoleic acid Ricinoleic acid (R)-12-hydroxy-(Z)-9-octadecenoic acid (R)-12- ydroxy-(Z)-9-ociadecenoic acid
  • ricinoleic acid used in the present invention may be prepared by any suitable means known to the person skilled in the art. Typically, fatty acids are produced from a parent oil via hydrolyzation and distillation. Triglyceride
  • the triglyceride contacted with the mono or di ester of glycerol and Moringa oil may be any suitable triglyceride.
  • the triglyceride may be obtained from any suitable oil from a plant source, oil from an animal source or oil from a marine source . Oils from a marine source include fish oils and oils from marine algae.
  • the triglyceride is obtained from any suitable plant oil.
  • the triglyceride is obtained from a plant oil selected from hard oils, soft oils and mixtures thereof and in particular is selected from palm oil, rape seed oil, sunflower oil, soybean oils, coconut oils, rice bran oils, dag oils, beef tallow, allanblackia oils and shea fat.
  • the triglyceride is selected from palm oil, palm stearine and palm olein.
  • the rate or degree of crystallisation of the triglyceride can be increased or retarded.
  • the mono or di ester of glycerol and Moringa oil increases the rate of crystallisation of a triglyceride.
  • the mono or di ester of glycerol and Moringa oil increases the extent of crystallisation of a triglyceride.
  • the mono or di ester of glycerol and Moringa decreases the extent of crystallisation of a triglyceride.
  • the mono or di ester of glycerol and Moringa increases the rate of crystallisation of a triglyceride
  • the mono or di ester of glycerol and Moringa increases the extent of crystallisation of a triglyceride.
  • the mono or di ester of glycerol and Moringa increase onset temperature of crystallisation of the triglyceride compared to the triglyceride in the absence of the mono or di ester of glycerol and Moringa oil.
  • the increase of onset temperature of crystallisation is at least 1°C.
  • the increase of onset temperature of crystallisation is at least 2°C.
  • the increase of onset temperature of crystallisation is at least 3°C.
  • the increase of onset temperature of crystallisation is at least 4°C.
  • the mono or di ester of glycerol and Moringa decrease onset temperature of crystallisation of the triglyceride compared to the triglyceride in the absence of the mono or di ester of glycerol and Moringa oil.
  • the decrease of onset temperature of crystallisation is at least 1°C.
  • the decrease of onset temperature of crystallisation is at least 2°C.
  • the decrease of onset temperature of crystallisation is at least 3°C.
  • the decrease of onset temperature of crystallisation is at least 4°C.
  • the present invention primarily relates to controlling crystallisation of a triglyceride
  • the triglyceride may contain further materials the crystallisation of which may also be controlled by the present mono- and diglycerides. These further materials include and are preferably selected from waxes, phytosterols, stanol esters and cholesterols. It will therefore be appreciated by one skilled in the art that the present invention provides for the control of crystallisation of a triglyceride and the control of crystallisation of a material selected from waxes, phytosterols, stanol esters and cholesterols.
  • the mono or di ester of glycerol and Moringa may be used to control crystallisation of a material selected from waxes, phytosterols, stano! esters and cholesterols independently of any control of crystallisation of a triglyceride.
  • the present invention provides:
  • a process for controlling the crystallisation of a material selected from waxes, phytosterols, stanol esters and cholesterols comprising the steps of (i) providing a material selected from waxes, phytosterols, stanol esters and cholesterols (ii) contacting the material selected from waxes, phytosterols, stanol esters and cholesterols with a mono or di ester of glycerol and Moringa.
  • composition comprising a mono or di ester of glycerol and Moringa to control the crystallisation of a material selected from waxes, phytosterols, stanol esters and cholesterols.
  • compositions comprising a mono or di ester of glycerol and Moringa to increase onset temperature of crystallisation of a material selected from waxes, phytosterols, stanol esters and cholesterols compared to the material selected from waxes, phytosterols, stanol esters and cholesterols in the absence of the of a composition comprising monoglycerides and diglycerides.
  • composition comprising a mono or di ester of glycerol and oringa to increase onset temperature of crystallisation of a materia! selected from waxes, phytosterols, stano! esters and cholesterols compared to the material selected from waxes, phytosterols, stanol esters and cholesterols in the absence of the composition comprising monoglycerides and diglycerides as described herein.
  • the material selected from waxes, phytosterols, stanol esters and cholesterols is preferably selected from bees wax, carnauba wax, vegetable waxes, rice bran wax, sunflower wax, jojoba wax, heRP70 (fatty acid composition containing 5% C16:0, 40% C18:0, 9% C20:0, and 43% C22:0, more than 99.5% of the fats of which are saturated), candelilla wax, ursolic acid, oleanolic acid, phytosterols, beta sitosterol, gamma oryzanoi, cyclodextrins, sphingolipids, 1 ,2-hydroxystearic acid, ricineiaidic acid, phospholipids of lecithin, phosphatidylinositol (PI), lysophosphatidylcholine (LPC), and phosphatidylcholine (PC).
  • bees wax carnauba wax, vegetable waxes, rice bran
  • Figure 1 and 2 show graphs
  • Figure 3 show an image
  • Figure 7 show an image
  • CRYSTALLIZER 110 the onset temperatures fell from 42.5X to 37°C to 32°C respectively for the three cooling rates above.
  • DIMODAN HP exhibited an onset temperature of 28°C
  • GRINDSTED® CRYSTALLIZER 1 10 is a fully saturated long chain monogiyceride based on C 22 0 .
  • GRINDSTED® PGPR 90 is Polyglycerol Polyricinoleate.
  • DIMODAN HP is a distilled monogiyceride made from edible, refined, hydrogenated palm oil.
  • the bulk fat blend showed onset of crystallisation at lower temperatures than
  • Monoglycerides of Moringa possess a bi-functionai role of template nucleating capability with surface stabilising activity - a role rendering them with commercially attractive and beneficial properties over and above not being limited in dosage or usage, as is PGPR.
  • moringa oil (Code: 126089, Batch Nr: DEO5040243, EO Ref: SO4903823/1 , from Earth Oil Plantations Limited). 2550g.
  • the moringa oil was extracted from Moringa oleifera (also known as Moringa pterygosperma).
  • the temperature was raised to 240°C under stirring and nitrogen blanketing.
  • the mixture was heated at 240°C until it became clear. When clear, the mixture was heated for further 30 min.
  • the mixture was deodorised in order to remove the free glycerol.
  • the set-up around the 3- necked flask was therefore changed to look like the below example of a deodorisation set- up:
  • the product was cooled to 90° and pressure equalised with nitrogen.
  • the filtered mono-diglyceride can be protected with antioxidants if the mono- diglyceride is the end product. Antioxidants were added and the mixture stirred for 15-30 min under nitrogen blanketing at 80-90 .
  • the mono-diglyceride was fiitered through filteraid (Clarcell) and paper filter (AGF 165- 1 10). 2472/191 : Distilled monogiyceride based on moringa o'l.
  • Mcno-digiyceride 191 Moringa Mcno-digiyceride 191 ; Moringa 191 ; MM 191 )
  • Mono-diglyceride (2472/173) 2 80g The mono-diglyceride was distilled on a short path distillation apparatus.
  • the distillation temperature was 210°C.
  • Table 1 composition of monogiyceride based on moringa oil The fatty acid composition of both the starting material, moringa oil, and the resulting monoglycende was also analysed:
  • Table 2 Fatty acid composition of moringa oil and the resulting monoglycende.
  • Moringa oil contains 10-12% of saturated fatty acids above C18.
  • the distillation temperature had to be chosen sufficiently high such that these at least were distilled.
  • Transferring the highest boiling monoglyceride components results in the monoglyceride as such having a higher content of diglyceride than is usually seen with distilled monoglycerides, but that is merely a consequence of the broad fatty acid composition in the moringa oil, and that the heavier monoglycerides were prioritised due to their also higher melting points.
  • the mixture was neutralised with 1.04g H 3 P0 4 (85%) at 240°C. After neutralisation the mixture was cooled to about 90°C and the mixture was deodorised and filtered as for above interesterification (2472/173).
  • Table 3 Composition of mono-diglyceride based on moringa oil
  • Table 4 Composition of mono-diglyceride based on moringa oil 2559/104: Distilled monoqiyceride based on moringa oil.
  • the mono-diglyceride was distilled on a short path distillation apparatus as above (2472/191 ).
  • Mono-diglyceride (2559/102) + (2559/103) are both distilled.
  • the distillation temperature was 200-210°C.
  • Table 5 Composition of monoglyceride based on moringa oi!
  • IMono-cisglyceride 105 Morioga Siono-digSycersde 105; Moringa 105; MM 105)
  • Table 6 Composition of mono-diglyceride used as raw material for distillation.
  • the mono-diglyceride was distilled on a short path distillation apparatus as above (2472/191 ).
  • the distillation temperature was 210°C.
  • Condenser was 85°C. Rotor speed 297 rpm.
  • Table 7 Composition of monoglyceride based on moringa oil
  • Table 8 Composition of mono-diglyceride used as raw material for distillation.
  • the mono-diglyceride was distilled on a short path distillation apparatus as above (2472/191 ).
  • the distillation temperature was 185°C. Reservoir temp, before heated surface 85°C.
  • Table 9 Composition of monoglyceride based on moringa oil.
  • Two fat blends with differing degrees of saturation were used as the solvent. First a blend consisting of 70% pa!m stearin (35 IV) and 30% palm olein (56 IV), then secondly a more unsaturated blend consisting of 70% palm olein (56 IV) and 30% palm stearin (35 !V), to which in both cases respectively, the emulsifiers GRINDSTED® CRYSTALLIZER 1 10, GRINDSTED® PGPR 90, and Monoglycerides of Moringa were added at 1 %, 0.5% and 1 % respectively. The fatty acid breakdown of the Monoglycerides of Moringa, Moringa 191 are given below.
  • Figure 2a shows a large portion of the graph from 70°C to about 45°C where there is only a gradual increase in viscosity. It is viewed that in this portion of the graph essentially nothing is happening to the fat based system due to the fact that it is regarded as a true melt, and therefore expected to behave in true Newtonian fashion. Below 45°C however, dramatic increases in viscosity can be seen, occurring at various temperatures depending on the nature of the sample in question.
  • Figures 2b and 2d show the expanded section of Figure 2a and 2c, where the data is expressed from 50°C and cooler.
  • Figures 2b and 2d show that GRINDSTED® CRYSTALLIZER 1 10 alone begins the onset of viscosity increase at 40°C and 38°C respectively, whereas the samples with the Crystalliser molecule and GRINDSTED® PGPR 90 or Monoglycerides of Moringa show an onset at 42.5°C and 41 °C respectively.
  • Figure 2d shows onset at 42°C and 38°C respectively.
  • Figure 2b shows GRINDSTED® PGPR 90 and Monoglycerides of Moringa first show an onset of viscosity rise at around 31-32°C, and the control sample increases from 34°C
  • Figure 2d shows GRINDSTED® PGPR 90 and Monoglycerides of Moringa first show an onset of viscosity rise at around 30-34°C, and the control sample increases from 27°C
  • GRINDSTED® PGPR 90 When mixed together with GRINDSTED® CRYSTALLIZER 1 10, there is however a clear distinction between GRINDSTED® PGPR 90 and Monoglycerides of Moringa.
  • the combination of GRINDSTED® CRYSTALLIZER 1 10 with GRINDSTED® PGPR 90 shows the earliest onset of viscosity rise, occurring at some 42.5°C. This can perhaps be attributed to two aspects of the characteristics of GRINDSTED® PGPR 90, crystal structure and surface activity respectively. It appears from micrographs that GRINDSTED® PGPR 90 possesses an inherent dendricity which manifests itself in the form of fern-like structures.
  • PGPR has a large adsorption capacity, and is possibly able to override Van der Waals attraction forces in the bulk, being less significant compared to interfacial structural forces (local polar interactions), and influenced by the presence of water, where the polar polyglycerol part of the molecule is strongly adsorbed to the water droplet surface. Strong molecular interaction kinetics (antifreeze behaviour) may influence the water droplet properties. Dealing with the bulk oil phase; investigations have demonstrated that only one layer of molecules is strongly affected at the surface (Claesson et al, 1997). Therefore a mechanism is proposed whereby a stabilised sub-micron crystalline formation, which is anchored by the non-polar polyricinoleate part of the PGPR occurs (Dedinaite &
  • Long range ordered structure may be less uniformly structured. While this is one possible explanation within a bulk liquid oil such as canola or triolein, it may not be the same mechanism if a more saturated solvent / mixture were used (Ghosh & Rousseau, 2009). Though not adequately explained here or understood, PGPR may lead to the creation of what can be thought of as a broken 'slush-ice' like structure, which result in adhesive properties, when mixed with another surfactant in the presence of water (Dedinaite & Campbell, 2000).
  • Figure 2d shows similar response behaviour in the inherently less saturated oil blend (and 70% palm olein / 30% palm stearin)
  • Figure 4a and 4b show the same rheological cooling profiles for the same samples, simply measured at the faster cooling rate of 10°C per minute. It is apparent that essentially the same trend is seen here, as was for the slower cooling rate of 1 °C per minute in Figures 2a and 2b. However, closer examination highlights a shift in onset temperature to lower values in Figure 4a and 4b.
  • Figure 4a shows the entire cooling curve and again indicates that the profile is basically uninteresting between 70°C and 40°C, whereupon below this temperature range the viscosity increase is seen.
  • Figure 4b therefore highlights a close up of the cooling curve starting at 45°C and down towards 25°C.
  • Monoglycerides of Moringa and GRINDSTED® PGPR 90 - show behavioural patterns that are the same (as seen at Sower temperature gradient), and basically follow the control sample, but the viscosity increase has dropped to lower temperatures.
  • GRINDSTED® CRYSTALLIZER 1 10 we can see that the onset of viscosity increase - gelation has moved again to lower temperatures, but still maintaining a distinct gap from the control and individual samples.
  • CRYSTALLIZER 1 10 is now the same at 32°C. There appears to be no difference between the sample containing GRINDSTED® PGPR 90 or Monoglycerides of Moringa.
  • GRINDSTED® CRYSTALLIZER 1 10 were 41 °C and 36°C respectively. At a cooling rate of 30°C per minute the onset temperature has fallen further to 32°C.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Fats And Perfumes (AREA)

Abstract

La présente invention concerne un procédé pour contrôler la cristallisation de triglycérides, le procédé comprenant les étapes de (i) production d'un triglycéride et (ii) mise en contact du triglycéride avec un mono‑ ou di-ester de glycérol et de l'huile de Moringa.
PCT/GB2012/051297 2011-06-09 2012-06-08 Cristallisation de graisse de triglycérides Ceased WO2012168727A1 (fr)

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GB1109649.2 2011-06-09
GBGB1109649.2A GB201109649D0 (en) 2011-06-09 2011-06-09 Process
US201161497739P 2011-06-16 2011-06-16
US61/497,739 2011-06-16
GBGB1117039.6A GB201117039D0 (en) 2011-10-04 2011-10-04 Process
GB1117039.6 2011-10-04

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004043364A2 (fr) * 2002-11-14 2004-05-27 International Flora Technologies, Ltd. Estes de moringa et preparations cosmetiques et pharmaceutiques, et procedes de fabrication associes

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004043364A2 (fr) * 2002-11-14 2004-05-27 International Flora Technologies, Ltd. Estes de moringa et preparations cosmetiques et pharmaceutiques, et procedes de fabrication associes

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