+

WO1993000823A1 - Produits comestibles contenant de la matiere grasse - Google Patents

Produits comestibles contenant de la matiere grasse Download PDF

Info

Publication number
WO1993000823A1
WO1993000823A1 PCT/EP1992/001429 EP9201429W WO9300823A1 WO 1993000823 A1 WO1993000823 A1 WO 1993000823A1 EP 9201429 W EP9201429 W EP 9201429W WO 9300823 A1 WO9300823 A1 WO 9300823A1
Authority
WO
WIPO (PCT)
Prior art keywords
fatty acid
polyol fatty
solid polyol
preferred
solid
Prior art date
Application number
PCT/EP1992/001429
Other languages
English (en)
Inventor
Volkmar Konrad MÜLLER
Original Assignee
Unilever N.V.
Unilever Plc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from EP91201819A external-priority patent/EP0467464B1/fr
Application filed by Unilever N.V., Unilever Plc filed Critical Unilever N.V.
Priority to EP92913229A priority Critical patent/EP0594646A1/fr
Publication of WO1993000823A1 publication Critical patent/WO1993000823A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • A23G3/346—Finished or semi-finished products in the form of powders, paste or liquids
    • 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
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/20—Reducing nutritive value; Dietetic products with reduced nutritive value
    • A23L33/21—Addition of substantially indigestible substances, e.g. dietary fibres
    • A23L33/25—Synthetic polymers, e.g. vinylic or acrylic polymers
    • A23L33/26—Polyol polyesters, e.g. sucrose polyesters; Synthetic sugar polymers, e.g. polydextrose
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G2200/00—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF containing organic compounds, e.g. synthetic flavouring agents
    • A23G2200/08—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF containing organic compounds, e.g. synthetic flavouring agents containing cocoa fat if specifically mentioned or containing products of cocoa fat or containing other fats, e.g. fatty acid, fatty alcohol, their esters, lecithin, paraffins

Definitions

  • the present invention relates to edible fat-containing products comprising an indigestible fat-replacer.
  • the term 'fat 1 refers to edible fatty substances in a general sense, including natural or synthesized fats and oils consisting essentially of triglycerides such as, for example, soybean oil, sunflower oil, palm oil, coconut oil, fish oil, lard and tallow, which may have been partially or completely hydrogenated or modified otherwise, as well as non-toxic fatty materials having properties similar to triglycerides, herein referred to as fat-replacers, which materials may be partially or fully indigestible.
  • fat and oil are used interchangeably.
  • non-triglyceride fatty substances have been described as potential fat-replacers in food products.
  • waxes e.g. jojoba oil and hydrogenated jojoba oil
  • polysiloxanes e.g. jojoba oil and hydrogenated jojoba oil
  • acylated glycerides e.g., acylated glycerides
  • polyal oxyglycerolethers e.g. acylated glycerides
  • dicarboxylic acid esters e.g.
  • polyol fatty acid polyesters and more specifically the sugar fatty acid polyesters, such as e.g. the sucrose fatty acid polyesters, are receiving increased attention as low-calorie fat-replacers in edible products.
  • sugar fatty acid polyesters such as e.g. the sucrose fatty acid polyesters
  • Polyol fatty acid polyesters are also reported to have use as pharmaceutical agents e.g. in view of their ability to take up fat-soluble substances, such as in particular cholesterol, in the gastro-intestinal tract, and subsequently remove those substances from the human body.
  • Suitable polyol fatty acid polyesters are derived from aliph ⁇ atic or aromatic polyols which comprise at least four free hydroxyl groups.
  • Such polyols in particular include the group of sugar polyols, which comprises the sugars, i.e. the mono-, di- and polysaccharides, the corresponding sugar alcohols and the derivatives thereof having at least four free hydroxyl groups.
  • sugar polyols examples include glucose, mannose, galactose, xylose, fructose, sorbose, tagatose, ribulose, xylulose, maltose, lactose, cellobiose, raffinose, sucrose, erythritol, mannitol, lactitol, sorbitol, xylitol and alpha- methylglucoside.
  • a particularly preferred polyol is sucrose.
  • polyol fatty acid polyester' is intended to refer to any such polyesters or mixtures thereof which have a degree of conversion of 70 % or more, i.e. of which, on an average, 70 % or more of the polyol hydroxyl groups have been esterified with fatty acids.
  • Preferred polyol fatty acid polyesters for use in the present invention have degrees of conversion of 85 % or more, or even 95 % or more.
  • the fatty acid residues in the polyol fatty acid polyesters may be derived from naturally occurring or synthetic fatty acids per se, or suitable sources thereof, such as natural triglyceride fats and oils or their corresponding lower-alkyl esters.
  • the fatty acids may be saturated or unsaturated, branched or straight fatty acids containing from 8 to 24 carbon atoms, in particular 12 to 18 carbon atoms, such as lauric, myristic, palmitic, stearic, oleic, elaidic, and linoleic acids.
  • Suitable natural sources are the vegetable oils, such as sunflower, safflower, rapeseed, cottonseed, palm kernel, palm and soybean oils.
  • oils for example marine oil or animal oil may be used. If so required, conventional techniques may be used to first introduce the necessary degree of saturation. Suitable such techniques include full or partial hydrogenation, interesterification, and fractionation, and may be used before or after conversio to the polyol fatty acid polyesters.
  • EP 233,856 discloses the use of intermediate melting polyol fatty acid polyesters for reducing problems of anal leakage and mouthfeel.
  • food products fried in these intermediate melting polyol fatty acid polyesters still hav a more waxy mouthfeel than products fried in triglyceride frying media.
  • WO 91/15960 discloses specific hardstock materials which may be used in blends of liquid and solid polyol fatty acids. These hardstock materials contain high levels of C 20 or higher saturated fatty acid materials. Similar hardstock materials are disclosed in WO 91/15961, WO 91/15963 and WO 91/15964 (P&G) .
  • WO 91/15962 discloses the use of from 10 to 40% of solid polyol fatty acid polyester materials in combination with 60 to 90% liquid non-digestible oils.
  • Preferred solid materials comprise 84.8% of saturated C 18 fatty acids.
  • the present invention relates to an edible composition
  • said fatty substances comprising a mixture comprising from 60-99% by weight of the mixture of liquid polyol fatty acid polyesters and from 1-40% by weight of the mixture of solid polyol fatty acid polyesters, characterised in that one or more of the following requirements are satisfied:
  • the solid polyol fatty acid polyester contains at least 10 wt% of C 12 _ 18 saturated fatty acid residues and the solid polyol fatty acid polyester has a beta-prime crystal morphology;
  • the solid polyol fatty acid polyester is present at a level of less then 20% by weight of the mixture and has an average particle size of less than 20 ⁇ m;
  • the fatty substances of the composition together have a thixotropic area of less than 200,000 Pa/s, and the solid polyol fatty acid polyester comprises at least 10 wt% of C 12 _ 18 saturated fatty acid residues, the weight ratio of C 16 to C 18 saturated fatty acid residues being from 5:1 to 1:5;
  • the fatty substances of the composition together have a thixotropic area of more than 200,000 Pa/s, and the solid polyol fatty acid polyester comprises at least 10 wt% of C 12 _ 18 saturated fatty acid residues, and the wt% of C 18 saturated fatty acid residues in the solid polyol fatty acid polyester is less than 90 wt%;
  • the level of solid polyol fatty acid polyesters is from 1 to 9% by weight of the mixture and the solid polyol fatty acid polyester material comprises at least 10 wt% of C 12 - 18 saturated fatty acid residues.
  • wt% for the fatty acid residues are based on the total weight of fatty acid residues in the solid polyol fatty acid polyester material.
  • Edible compositions in accordance to the invention comprise fatty substances.
  • fatty substance refers to edible fatty substances which may be fully or partially indigestible.
  • compositions of the invention may comprise digestible fatty substances such as triglyceride materials and non-glyceride fatty substances.
  • the level of these fatty substances other than the polyol fatty acid polyesters may be up to 90 wt%, based on the total weight of the fatty substances, preferably, however the level is from 0-40 wt%, more preferred 0-10 wt%, most preferred edible compositions of the invention are substantially free from fatty substances other than polyol fatty acid polyesters.
  • the total level of fatty substances in the edible composition of the invention may be from 1-100 wt%, for example 5-95 wt%.
  • Some edible compositions like shortenings, chocolate and dressings may comprise relatively high levels of fatty substances, for example 30-90 wt%.
  • Other edible compositions like sauces, soups, bakery products etc may comprise lower levels of fatty substances for example 1-30 wt%.
  • the fatty substances which are present in the edible compositions of the invention comprise a mixture of liquid and solid polyol fatty acid polyester materials, the level of liquid polyol fatty acid polyesters in the mixture being from 60-99 wt%, more preferred 70-97 wt%, most preferred 80-95 wt% and the level of solid polyol fatty acid polyesters being from 1-40 wt%, more preferred 3-30 wt%, most preferred 5-20 wt%, the percentages being based on the total weight of the mixture of liquid and solid polyol fatty acid polyesters.
  • the liquid polyol fatty acid polyester material may be any material which in physical properties and rheology behaves similar to conventional liquid materials and which has a complete melting point below 35°C, more preferred below 30°C, most preferred less than 20°C. Examples thereof are given in the examples. Also mixtures of liquid polyol fatty acid polyesters may be used as the liquid component of the mixture.
  • the solid fatty acid polyester material may be any material satisfying one or more of the requirements of the invention and which has a complete melting point above 35°C, more preferred above 40°C most preferred above 45°C. Examples of solid materials are given in the examples. Also mixtures of solid polyol fatty acid polyesters may be used.
  • the mixture of liquid and solid polyol fatty acid polyesters hence is preferably characterised by the presence of at leas two peaks as measured with differential scanning calorimetry one of the peaks below 35°C and one of the peaks above 35°C, more preferably one peak below 30°C and one above 40°C, most preferred one peak below 25°C and one above 45°C.
  • the optional conventional fat-component may be triglyceride oils or fats of animal or vegetable origin.
  • Suitable conventional triglyceride fats and oils include, optionally partially or fully hydrogenated, coconut oil, palmkernel oil, palm oil, marine oils, lard, tallow fat, butter fat, cocoa butter fat, soybean oil, safflower oil, cotton seed oil, rapeseed oil, corn oil sunflower oil and mixtures thereof.
  • the solid polyol fatty polyester contains at least 10 wt% of C 12 _ 18 saturated fatty acid residues and the solid fatty acid has a beta-prime crystal morphology.
  • these particular solid polyol fatty acid polyester materials comprising a minimum amount of saturated C 12 _ 18 fatty acid residues and which exhibit beta-prime morphology are particularly advantageous because these materials are believed to be capable of network formation in the liquid /solid mixtures, therewith providing anti-leakage properties and/or improved rheology.
  • the level of saturated C 12 _ 18 fatty acid residues in the solid polyol fatty acid polyester is from 10-100 wt%, more preferred 60-100%, most preferred 80-100%.
  • the solid polyol fatty acid polyester has a beta-prime morphology.
  • beta prime morphology can be shown to be present with conventional techniques.
  • Preferably at least 10 wt%, more preferred more than 25%, most preferred from 50-100% of the solid polyol fatty acid polyester is present in the form of beta-prime crystals. The presence of these crystals can be detected by known techniques such as X-ray diffraction.
  • the solid polyol fatty acid polyester material is present at a level of less than 20% by weight of the mixture of polyol fatty acid ester materials, more preferred from 2-15%, most preferred from 3- 10% and has an average particle size of less than 20 ⁇ m, more preferred from 0.01 to 10 ⁇ m, most preferred from 0.1 to 7 ⁇ m. It is believed that these relatively low levels of solid polyol fatty acid polyester materials combined with their small particle size, again give rise to the formation of a network structure in the liquid/solid mixtures of the invention therewith providing anti-leakage properties and/or improved rheology and/or improved non-waxy mouthfeel and/or reduced graininess.
  • the average particle size can advantageously be measured by conventional techniques, such as light microscopy; preferably prior to measurement of the particle size the sample is subjected to moderate shear for temporarily breaking up a network system that might eventually be present.
  • the fatty substances of the composition together have a thixotropic area of less than 200,000 Pa/s (preferred 10,000 to 100,00, more preferred 15,000 to 50,000 Pa/s), and the solid polyol fatty acid polyester comprises at least 10 wt%, more preferred 20-90%, most preferred 30-80% of C 12 _ 18 saturated fatty acid residues, the weight ratio of C 16 to C 18 saturated fatty acid residues being from 5:1 to 1:5.
  • the fatty substances of the composition together have a relatively low thixotropic area, then the network formation to provide good rheology and/or mouthfeel and/or anti-leakage is best safeguarded if the level of C 12 _ 18 saturated fatty acid residues in the solid polyol fatty acid polyester is at least 10 wt% and the ratio of C 16 to C 18 is from 5:1 to 1:5 more preferred from 3:1 to 1:3, most preferred 2:1 to 1:2.
  • the thixotropic area of the composition can be determined by any conventional method, preferably the method as described in WO 91/15962 is used. Another preferred method is described in the examples.
  • the fatty substances of the composition together have a thixotropic area of more than 200,000 Pa/s
  • the solid polyol fatty acid polyester comprises at least 10 wt% more preferred 20-90%, most preferred 30-80% of C 12 _ 18 saturated fatty acid residues, and the wt% of C 18 saturated fatty acid residues in the solid polyol fatty acid ester material is less than 90 wt%, more preferred less than 87%, most preferred less than 80% of the fatty acid ester residues.
  • the fatty substances of the composition together have a relatively high thixotropic area, then the network formation to provide good rheology and/or mouthfeel and/or anti-leakage is best safeguarded if the level of fatty acid residues in the solid polyol fatty acid polyester of C 12 _ 18 saturated fatty acids is at least 10 wt%, provided the level of C 18 saturated fatty acid residues is less than 90 wt%.
  • the level of solid polyol fatty acid polyesters is from 1 to 9% by weight of the mixture of polyol fatty acid polyester materials and the solid polyol fatty acid polyester material comprises at least 10 wt%, more preferred 20-80%, most preferred 30-70% of C 12 _ 18 saturated fatty acid residues. It is believed that these relatively low levels of solid polyol fatty acid polyesters with relatively high levels of C 12 _ 18 saturated fatty acids are capable of providing advantageous network properties resulting in good rheology and/or anti-leakage and/or non- waxy mouthfeel.
  • the solid polyol fatty acid polyester comprises a certain minimum level of saturated fatty acid residues.
  • the level of unsaturated fatty acid residues in the solid polyol fatty acid ester may in theory be up to 100%, although generally lower levels, for example 0-60 wt% or 10-40 wt% will be used.
  • the level of C 20 or higher fatty acid residues in the solid polyol fatty acid polyester is preferably less than 60 wt%, more preferred less than 40%, most preferred from 0-10%.
  • Preferred embodiments of the invention relate to compositions satisfying two or more of the above mentioned conditions.
  • preferred edible compositions satisfy at least one requirement of the group of (a) and (b) plus at least one requirement of the group of (c) , (d) and (e) .
  • compositions satisfying both requirements (a) and (b) most preferred in combination with at least one of the requirements of (c) , (d) and (e) .
  • rheology the selection of the appropriate fat- replacer or mixture of fat-replacer and conventional fat strongly depends upon the particular application envisaged, and may range of fat-replacers having a fully fluid rheology to replace liquid oils in e.g. salad, frying or seasoning oils, to more viscous or even solid rheology in compositions having a more structured fat phase such as margarines, spreads, shortenings and confectionery products.
  • the present invention is not specific to edible fat- containing compositions in any particular food area. It may be suitably be applied to food products such as spreads, margarines, creams, salad oils, frying oils, shortenings, bakery products such as doughs, cakes and biscuits, fried an snack products, fresh, hard and processed cheeses, meat emulsions, mayonnaise and dressings, confectionery products, such as desserts, fillings, chocolates, candies, chews, and ice-creams.
  • food products such as spreads, margarines, creams, salad oils, frying oils, shortenings, bakery products such as doughs, cakes and biscuits, fried an snack products, fresh, hard and processed cheeses, meat emulsions, mayonnaise and dressings, confectionery products, such as desserts, fillings, chocolates, candies, chews, and ice-creams.
  • the octaester content of this material is 78.1%, the OH value 6.1 and the clearpoint as measured with DSC of about 20°C.
  • Spe 2 has a OH value of 3.4 and a clearpoint (DSC) of 59.5°C spe3 has a OH-value of 4.1 and a clearpoint (DSC) of 55 °C.
  • Example II A mixture of 90 wt% of spel and 10 wt% spe2 is plastized in scraped tubular surface heat exchangers (A-units) .
  • the A- units had a volume of 18 ml, a split of 3 ml and 2 scraper blades.
  • the speed of the rotating blades amounted to 500 rpm, at a throughput of 3 kg/hr.
  • the system is cooled to have an outlet temperature of the first A-unit of 41°C and 20°C for the second A-unit.
  • the average particle size as determined b light microscopy (sample of 0.01 mm thickness prepared in a 0.01 m Leitz culture chamber, measured with polarized light at ambient temperature magnification 100 times, resolution about 1 ⁇ m) was less than 10 ⁇ m (estimated 4-6 ⁇ m) .
  • the thixotropic area of the sample at 33.3 °C was significantly less than 200,000 Pa/s and was determined as follows: The sample is tempered by pouring 5 g of fatty substance after melting in glass-tubes (diameter 10 mm, wall thickness 1 mm) followed by heating to 80°C for 30 minutes, The heated sample is then cooled in a water bath of 5°C until a temperature is reached of 29.4°C. The cooled sample is then stored for 1 week at 21.1°C. The thixotropic area of the sample is then determined as follows: The viscometer is kept at 33.3°C, the temperature of the sample is adjusted to this temperature.
  • the shear rate is linearly increased from 0 s -1 to 800 s -1 in 2 minutes and then reduced back to 0 s -1 in another 2 minutes in a Ferranti Shirley viscometer.
  • the thixotropic area is the area encompassed by the hystheresis loop in the shear rate versus the shear stress plot.
  • Example II was repeated when using a mixture of 90% spel and 10% of spe3. Again the average particle size of the hardstock material was less than 10 ⁇ m and the thixotropic area was far less than 200,000 Pa/s.
  • a mixture of 92 wt% spel and 8 wt% spe3 was prepared and crystallised by cooling to 20°C with tap water in a stirred vessel (content 50g) .
  • the thixotropic area was determined as in example II and was far less than 200,000 Pa/s. Similar results were obtained for mixtures of 92 wt% spel and 8 wt% spe4 or spe5., and mixtures of 70% spel and 30% of spe2 or spe3.
  • a mixture of 73 wt% of trans-hardened soybean oil (slip melting point 36°C) , 4% fully hardened palm oil, 21 wt% spel and 2 wt% spe3 was prepared.
  • the thixotropic area was determined as in example II and was significantly more than 200,000 Pa/s.
  • sucrose octastearate was crystallised into beta prime structure, according to the method as described in Jandacek and Webb, Chemistry and Physics of Lipids (1978) 163-176.
  • a mixture was prepared of 65 wt% spel and 35 wt% of the sucrose octastearate. The mixture is evaluated by X-ray diffraction and shows beta prime crystal morphology.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Mycology (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Edible Oils And Fats (AREA)

Abstract

On estime que des mélanges de polyesters d'acides gras aux polyols liquides et solides présentent une réhologie et/ou des propriétés antidiarréhiques favorables et/ou un goût meilleur.
PCT/EP1992/001429 1991-07-12 1992-06-25 Produits comestibles contenant de la matiere grasse WO1993000823A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP92913229A EP0594646A1 (fr) 1991-07-12 1992-06-25 Produits comestibles contenant de la matiere grasse

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP91201819A EP0467464B1 (fr) 1990-07-20 1991-07-12 Composition contenant de la graisse alimentaire
EP91201819.9 1991-07-12
EP92200138.3 1992-01-17
EP92200138 1992-01-17

Publications (1)

Publication Number Publication Date
WO1993000823A1 true WO1993000823A1 (fr) 1993-01-21

Family

ID=26129323

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1992/001429 WO1993000823A1 (fr) 1991-07-12 1992-06-25 Produits comestibles contenant de la matiere grasse

Country Status (1)

Country Link
WO (1) WO1993000823A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994005165A1 (fr) * 1992-08-28 1994-03-17 The Procter & Gamble Company Frites et autres aliments enrobes de matiere grasse et a teneur elevee en humidite, presentant un aspect moins graisseux et une teneur reduite en calories
WO1994023592A1 (fr) * 1993-04-08 1994-10-27 The Procter & Gamble Company Chips a teneur diminuee en calories obtenues en faisant frire des tranches de pommes de terre crues dans une composition de matiere grasse a teneur diminuee en calories et en eliminant une portion de ladite composition de matiere grasse des chips
WO1994023591A1 (fr) * 1993-04-08 1994-10-27 The Procter & Gamble Company Collation legere a teneur reduite en calories, contenant une composition de matiere grasse pauvre en calories, frite dans ladite composition de matiere grasse ou enrobee de ladite composition de matiere grasse
WO1998052428A3 (fr) * 1997-05-20 1999-02-25 Procter & Gamble Composition fluide et son procede d'obtention
US6335048B1 (en) * 1998-02-20 2002-01-01 Recot, Inc. Interconvertible solid and liquid states of Olestra
US6432465B1 (en) 1996-07-01 2002-08-13 The Procter & Gamble Co. Dough compositions used to prepare reduced and low-calorie snacks
US6562394B1 (en) * 1998-05-20 2003-05-13 The Procter & Gamble Co. Flowable nondigestible oil and process for making
US6890580B1 (en) 1999-04-26 2005-05-10 Procter + Gamble Co. Method for preparing dehydrated starch products
US7276485B1 (en) 1997-04-21 2007-10-02 The Procter + Gamble Co. Flowable nondigestible oil and process for making

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4005195A (en) * 1976-02-12 1977-01-25 The Procter & Gamble Company Compositions for treating hypercholesterolemia
EP0233856A2 (fr) * 1986-02-20 1987-08-26 The Procter & Gamble Company Matières grasses basses calories à saveur améliorée
EP0375027A2 (fr) * 1988-12-22 1990-06-27 The Procter & Gamble Company Compositions de corps gras à haute teneur en solides
WO1991015964A1 (fr) * 1990-04-26 1991-10-31 The Procter & Gamble Company Frites a teneur calorifique reduite et autres aliments contenant des matieres grasses, a faible teneur en humidite et ayant une texture moins cireuse et un meilleur gout

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4005195A (en) * 1976-02-12 1977-01-25 The Procter & Gamble Company Compositions for treating hypercholesterolemia
EP0233856A2 (fr) * 1986-02-20 1987-08-26 The Procter & Gamble Company Matières grasses basses calories à saveur améliorée
EP0375027A2 (fr) * 1988-12-22 1990-06-27 The Procter & Gamble Company Compositions de corps gras à haute teneur en solides
WO1991015964A1 (fr) * 1990-04-26 1991-10-31 The Procter & Gamble Company Frites a teneur calorifique reduite et autres aliments contenant des matieres grasses, a faible teneur en humidite et ayant une texture moins cireuse et un meilleur gout

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994005165A1 (fr) * 1992-08-28 1994-03-17 The Procter & Gamble Company Frites et autres aliments enrobes de matiere grasse et a teneur elevee en humidite, presentant un aspect moins graisseux et une teneur reduite en calories
WO1994023592A1 (fr) * 1993-04-08 1994-10-27 The Procter & Gamble Company Chips a teneur diminuee en calories obtenues en faisant frire des tranches de pommes de terre crues dans une composition de matiere grasse a teneur diminuee en calories et en eliminant une portion de ladite composition de matiere grasse des chips
WO1994023591A1 (fr) * 1993-04-08 1994-10-27 The Procter & Gamble Company Collation legere a teneur reduite en calories, contenant une composition de matiere grasse pauvre en calories, frite dans ladite composition de matiere grasse ou enrobee de ladite composition de matiere grasse
US6432465B1 (en) 1996-07-01 2002-08-13 The Procter & Gamble Co. Dough compositions used to prepare reduced and low-calorie snacks
US7276485B1 (en) 1997-04-21 2007-10-02 The Procter + Gamble Co. Flowable nondigestible oil and process for making
AU735920B2 (en) * 1997-05-20 2001-07-19 Procter & Gamble Company, The A flowable nondigestible oil and process for making
AU735923B2 (en) * 1997-05-20 2001-07-19 Procter & Gamble Company, The A flowable composition and a process for making the flowable composition
CN1085940C (zh) * 1997-05-20 2002-06-05 普罗克特和甘保尔公司 制作易流动的不易消化的油组合物的方法
CN1086278C (zh) * 1997-05-20 2002-06-19 普罗克特和甘保尔公司 制备易流动的不易消化的油组合物的方法
WO1998052429A3 (fr) * 1997-05-20 1999-02-25 Procter & Gamble Huile fluide non digestible et procede de fabrication
US6518226B2 (en) * 1997-05-20 2003-02-11 The Procter & Gamble Co. Flowable composition and a process for making the flowable composition
WO1998052428A3 (fr) * 1997-05-20 1999-02-25 Procter & Gamble Composition fluide et son procede d'obtention
US6335048B1 (en) * 1998-02-20 2002-01-01 Recot, Inc. Interconvertible solid and liquid states of Olestra
US6562394B1 (en) * 1998-05-20 2003-05-13 The Procter & Gamble Co. Flowable nondigestible oil and process for making
US6890580B1 (en) 1999-04-26 2005-05-10 Procter + Gamble Co. Method for preparing dehydrated starch products

Similar Documents

Publication Publication Date Title
EP0304131B1 (fr) Composition contenant de la graisse alimentaire et procédé pour la préparer
JP3124033B2 (ja) 受動的オイルロスコントロールのために多様エステル化ポリオールポリエステルを含有した非消化性脂肪組成物
AU668007B2 (en) Solid nondigestible polyol polyesters containing esterified hydroxy fatty acids such as esterified ricinoleic acid
CA2145999C (fr) Compositions lipidiques non digestibles renfermant un melange cocristallise de polyol polyester et un modificateur de cristal comme agent de controle de la perte passive d'huiles
CA2004723C (fr) Compose de matieres grasses a forte teneur en solides
US6022578A (en) Tablespread product containing liquid fat and process for preparing same
DE69207763T2 (de) Polyol fettsaürepolyester enthaltende backöle
WO1993000823A1 (fr) Produits comestibles contenant de la matiere grasse
US5102683A (en) Fatty compositions with high solids content
JPH05506988A (ja) 新規固体非消化性脂肪様化合物及びそれを含有した食品組成物
EP0350987B1 (fr) Composition comestible
WO1995028847A1 (fr) Produit gras a tartiner contenant des graisses liquides et procede de preparation dudit produit
EP0383380B1 (fr) Compositions contenant des graisses alimentaires
EP0594646A1 (fr) Produits comestibles contenant de la matiere grasse
US5211979A (en) Polyol fatty polyesters having newtonian rheology
EP0467464B1 (fr) Composition contenant de la graisse alimentaire
WO1993022932A1 (fr) Produits alimentaires contenant des matieres grasses
EP0434150A2 (fr) Produits contenant une graisse comestible
WO1993019077A1 (fr) Produits comestibles renfermant des graisses
EP0611526A1 (fr) Compositions alimentaires contenants de la graisse
EP0449350A1 (fr) Composition contenant de la graisse alimentaire et procédé pour la préparer
EP0443648A1 (fr) Composition contenant de la graisse alimentaire
CZ410599A3 (cs) Tekutý přípravek a způsob přípravy
CZ406399A3 (cs) Tekutý nestravitelný olej a způsob přípravy

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IT NL SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
WWE Wipo information: entry into national phase

Ref document number: 1992913229

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 1992913229

Country of ref document: EP

ENP Entry into the national phase

Ref country code: US

Ref document number: 1994 178318

Date of ref document: 19940531

Kind code of ref document: A

Format of ref document f/p: F

WWW Wipo information: withdrawn in national office

Ref document number: 1992913229

Country of ref document: EP

点击 这是indexloc提供的php浏览器服务，不要输入任何密码和下载