US20110124746A1 - Alkenyl succinic acid anhydride half ester emulsifier - Google Patents

Alkenyl succinic acid anhydride half ester emulsifier Download PDF

Info

Publication number
US20110124746A1
US20110124746A1 US12/626,463 US62646309A US2011124746A1 US 20110124746 A1 US20110124746 A1 US 20110124746A1 US 62646309 A US62646309 A US 62646309A US 2011124746 A1 US2011124746 A1 US 2011124746A1
Authority
US
United States
Prior art keywords
starch
emulsion
oil
water
present
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.)
Abandoned
Application number
US12/626,463
Other languages
English (en)
Inventor
Ralph Trksak
Afaf Makarious
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Brunob II BV
Ingredion Inc
National Starch LLC
Original Assignee
National Starch and Chemical Corp
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 to US12/626,463 priority Critical patent/US20110124746A1/en
Application filed by National Starch and Chemical Corp filed Critical National Starch and Chemical Corp
Priority to US12/687,782 priority patent/US7829600B1/en
Assigned to NATIONAL STARCH LLC, BRUNOB II B.V. reassignment NATIONAL STARCH LLC ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MAKARIOUS, AFAF, TRKSAK, RALPH
Priority to ZA2010/07836A priority patent/ZA201007836B/en
Priority to AU2010241234A priority patent/AU2010241234B2/en
Priority to MYPI2010005271 priority patent/MY150807A/en
Priority to MX2010012510A priority patent/MX2010012510A/es
Priority to ARP100104297A priority patent/AR079113A1/es
Priority to EP10191815.9A priority patent/EP2330134B1/de
Priority to CA2721888A priority patent/CA2721888C/en
Priority to PE2010001075A priority patent/PE20110518A1/es
Priority to CL2010001281A priority patent/CL2010001281A1/es
Priority to SG201008661-9A priority patent/SG171564A1/en
Priority to JP2010261325A priority patent/JP5912012B2/ja
Priority to TW099140474A priority patent/TWI522048B/zh
Priority to RU2010147913/13A priority patent/RU2528026C2/ru
Priority to CN201010555820.9A priority patent/CN102151516B/zh
Priority to BRPI1004713-1A priority patent/BRPI1004713B1/pt
Publication of US20110124746A1 publication Critical patent/US20110124746A1/en
Abandoned legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L3/00—Compositions of starch, amylose or amylopectin or of their derivatives or degradation products
    • C08L3/04—Starch derivatives, e.g. crosslinked derivatives
    • C08L3/06—Esters
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/10—Foods or foodstuffs containing additives; Preparation or treatment thereof containing emulsifiers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/062—Oil-in-water emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/732—Starch; Amylose; Amylopectin; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B31/00—Preparation of derivatives of starch
    • C08B31/02—Esters
    • C08B31/04—Esters of organic acids, e.g. alkenyl-succinated starch
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/017—Mixtures of compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/34—Higher-molecular-weight carboxylic acid esters
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]

Definitions

  • This invention relates to the preparation of a novel emulsifier; emulsions prepared with the emulsifier; and products prepared utilizing the emulsifier.
  • Half-ester starch derivatives may be created by reacting starch and a substituted dicarboxylic acid anhydride so as to form alkenyl succinic anhydride starch derivatives.
  • Native starch granules are insoluble in cold water. When native starch granules are dispersed in water and heated, however, they become hydrated and swell. With continued heating, shear, or conditions of extreme pH, the granules fragment and the starch molecules are dispersed in the water, i.e., solubilized, resulting in a nongranular, dispersed starch.
  • the invention comprises an emulsifier product that is a starch half ester of an alkenyl succinic anhydride.
  • the starch half ester of an alkenyl succinic anhydride has a water fluidity of no more than 75, is prepared by a dispersed phase process, and, when used to prepare a test oil-in-water emulsion with the starch half ester of an alkenyl succinic anhydride as a sole emulsifier at a w/w ratio of the starch half ester of an alkenyl succinic anhydride:oil of 1:4 with a 20% by weight oil load, creates a test oil-in-water emulsion characterized by at least the following: a) no more than about 5% of the oil particles of the emulsion greater than 1 micron after 24 hours at 57 C as assessed by polarization intensity differential plus elastic light scattering; and b) a Brookfield viscosity of the emulsion of less than about
  • the starch emulsifier product is a half ester of dodecenyl or octenyl succinic anhydride.
  • the water fluidity of the starch emulsifier product is not greater than 65.
  • the water fluidity of the starch emulsifier product is not greater than 40.
  • the water fluidity of the starch emulsifier product is not greater than 20.
  • the starch emulsifier product is a half ester of an octenyl succinic anhydride and the water fluidity of the starch emulsifier product is not greater than 40.
  • the average particle size of the starch emulsifier product may be characterized as less than one micron, as assessed by Polarization Intensity Differential Plus Elastic Light Scattering (Beckman Coulter LS 13 320 Aqueous Module).
  • a test oil-in-water emulsion prepared using the starch emulsifier product as a sole emulsifier is characterized by having a ratio of the starch half ester of an alkenyl succinic anhydride:oil of 1:6.
  • a test oil-in-water emulsion is prepared using the starch emulsifier product as sole emulsifier, wherein the test oil-in-water emulsion has a 24% by weight oil load.
  • an emulsion comprising an oil; a water; and a starch
  • the starch is a half ester of an alkenyl succinic anhydride
  • the starch is prepared by a dispersed phase process
  • the starch is characterized by a water fluidity of no more than 75, and wherein the starch is characterizable by the following:
  • the test oil-in-water emulsion when the starch is used to prepare a test oil-in-water emulsion with the starch as a sole emulsifier at a w/w ratio of the starch:oil of 1:4 and an oil load of 20% by weight, the test oil-in-water emulsion is characterized by at least the following: a. no more than about 5% of oil particles of the test oil-in-water emulsion greater than 1 micron after 24 hours at 57 C as assessed by polarization intensity differential plus elastic light scattering; and b. a Brookfield viscosity of the test oil-in-water emulsion of less than about 2000 cps after about one week of storage at 5 C, as assessed by Brookfield Programmable DV-1 Viscometer.
  • an emulsion comprising a starch; oil; and water; wherein the starch is a half ester of a dodecenyl succinic anhydride.
  • an emulsion comprising a starch; oil; and water; wherein the starch is a half ester of an octenyl succinic anhydride.
  • an emulsion comprising a starch; oil; and water; wherein the water fluidity of the starch is no greater than 65.
  • an emulsion comprising a starch; oil; and water; wherein the water fluidity of the starch is not greater than 40.
  • an emulsion comprising a starch; oil; and water; wherein the starch is a half ester of an octenyl succinic anhydride and the water fluidity of the starch is no greater than 40.
  • an emulsion wherein the starch and the oil are present in the emulsion in a ratio of 1:4 and wherein the oil is present in an amount of 12% (w/w) based on the emulsion.
  • an emulsion wherein the starch and the oil are present in the emulsion in a ratio of 1:4 and wherein the oil is present in an amount of 20% (w/w) based on the emulsion.
  • an emulsion wherein the starch and the oil are present in the emulsion in a ratio of 1:4 and wherein the oil is present in an amount of 24% (w/w) based on the emulsion.
  • an emulsion wherein the starch and the oil are present in the emulsion in a ratio of 1:6 and wherein the oil is present in an amount of 12% (w/w) based on the emulsion.
  • an emulsion wherein the starch and the oil are present in the emulsion in a ratio of 1:6 and wherein the oil is present in an amount of 20% (w/w) based on the emulsion.
  • an emulsion wherein the starch and the oil are present in the emulsion in a ratio of 1:6 and wherein the oil is present in an amount of 24% (w/w) based on the emulsion.
  • an emulsion comprising a starch; oil; and water; wherein the ratio of the starch to the oil is 1:6 and wherein the oil is present in an amount of 24% (w/w) based on the emulsion.
  • half ester of an alkenyl succinic anhydride means: a derivative prepared by chemical modification of a starch with an alkenyl succinic anhydride derivative.
  • alkenyl succinic anhydride means: an organic compound with the molecular formula RC 4 H 3 O 3 wherein R is an alkenyl group. It is the acid anhydride of a substituted succinic acid.
  • OSA means octenyl succinic anhydride
  • Frnel Viscosity means a viscosity test whereby the flow rate of a specific volume of a starch dispersion is measured using a precisely defined glass funnel according to the following procedure.
  • Funnel Viscosity may be determined, in one embodiment, by adjusting the starch dispersion to be tested to 8.5% solids (w/w), measured by refractometer. The temperature of the dispersion is controlled at 22° C. A total of 100 ml of the starch dispersion is measured into a graduated cylinder. It is then poured into a calibrated funnel while using a finger to close the orifice. A small amount is allowed to flow out of the funnel into the graduated cylinder to remove any trapped air and the balance is poured back into the funnel.
  • the finger is then removed to allow the contents to flow out of the funnel and a timer is used to measure the time required for the 100 ml sample to flow through the apex (junction of the stem and funnel body) of the funnel. This time is recorded and is identified as the funnel viscosity, measured in seconds.
  • the glass portion of the funnel is a standard 58°, thick-wall, resistance glass funnel whose top diameter is about 9 to about 10 cm with the inside diameter of the stem being about 0.381 cm.
  • the glass stem of the funnel is cut to an approximate length of 2.86 cm from the apex, carefully fire-polished, and refitted with a long stainless steel tip which is about 5.08 cm long with an outside diameter of about 0.9525 cm.
  • the interior diameter of the steel tip is about 0.5952 cm at the upper end where it is attached to the glass stem and about 0.4445 cm at the outflow end with the restriction in the width occurring at about 2.54 cm from the ends.
  • the steel tip is attached to the glass funnel by means of a Teflon tube.
  • the funnel is calibrated so as to allow 100 ml of water to go through in six seconds using the above procedure.
  • water fluidity means a test of viscosity measured on a scale of 0-90. Water fluidity is measured using a Bohlin Visco 88 Rotational Viscometer with water jacket (commercially available from Malvern Instruments, Inc., Southborough, Mass.), standardized at 30° C. with a standard oil having a viscosity of 100.0 cps. The water fluidity is obtained by determining the viscosity at a 8.06% solids level and converting that viscosity to a water fluidity (WF) value using the equation below. The procedure involves adding the required amount of starch (e.g., 10.0 g. dry basis) to a stainless steel cup and adding 14 g. distilled water to make a paste.
  • starch e.g., 10.0 g. dry basis
  • starch or “low amylose” means a starch or starch-containing product (herein starch or starch-containing product shall be referred to as starch) containing less than 10% amylose by weight, in one embodiment less than 5%, in another less than 2% and in yet another embodiment less than 1% amylose by weight of the starch.
  • high amylose means a starch containing at least 50% amylose by weight, in one embodiment at least 70%, in another at least 80% and in yet another embodiment at least 90% amylose by weight of the starch.
  • starch containing product means any product containing starch, including without limitation, flour and grits.
  • oil load is intended to mean the amount of oil in the emulsion based upon the entire emulsion and is measured on a weight percentage basis.
  • the term “Polarization Intensity Differential Plus Electric Light Scattering” means the use of the polarization effects of scattered light so as to estimate the particle size of very small objects.
  • Vertically polarized scattered light has different scattering patterns and fine structures from that of horizontally polarized light for small particles.
  • the main characteristic of the horizontal scattering intensity (I h ) for small particles is that there is a minimum around 90 degrees. This minimum shifts to larger angles for larger particles.
  • both vertical scattering intensity (I v ) and horizontal scattering intensity (I h ) have only small contrast in the case of small particles, the difference between them can reveal a more distinguished fine structure, thereby making the sizing of small particles possible.
  • the process may be extended to the lower sizing limit to as low as 40 nm without extrapolation.
  • This combined approach is known as the Polarization Intensity Differential Scattering (PIDS) technique (Beckman Coulter).
  • PIDS Polarization Intensity Differential Scattering
  • the PIDS signal is termed the PIDS signal.
  • the PIDS signal is roughly a quadratic curve centered at 90 degrees.
  • the pattern shifts to smaller angles and secondary peaks appear due to the scattering factor. Since the PIDS signal is dependent on particle size relative to light wavelength, valuable information about a particle size distribution can be obtained by measuring the PIDS signal at several wavelengths.
  • Brookfield viscosity means viscosity determined through measurements performed by the Brookfield Programmable DV-I Viscometer at given measurement conditions (spindle S63@60 rpm with a reading taken 15 sec after the start of rotation) at room temperature (i.e. 22° C.).
  • the principal of operation of the DV-I is to drive or rotate a spindle (which is immersed in the test fluid) through a calibrated spring.
  • the viscous drag of the fluid against the spindle is measured by the spring deflection.
  • Spring deflection is measured with a rotary transducer which translates the drag into viscosity of the test fluid through an internal calibration.
  • the measurement range (in centipoises or milliPascal seconds) is determined by the rotational speed of the spindle, the size and shape of the spindle, the container (in one embodiment, an 8 ounce tall glass bottle having dimensions of 2.25′′ width ⁇ 5′′ height) that the spindle is rotating in, and the full scale torque of the calibrated spring.
  • test oil-in-water emulsion means an emulsion prepared by the process by which a pre-emulsion is first made by slowly adding the oil blend to a starch dispersion (starch in aqueous phase) stirring with an LCI high shear mixer (Model HSM-100 LCI from Charles Ross & Son Company) at 5000 rpm for 2 minutes.
  • the above pre-emulsion is subsequently homogenized by two passes through an APV pressure homogenizer (Model 15 MR Laboratory Homogenizer from APV Gaulin); with the second stage set at 500 psi and the first stage set at 3000 psi for 12% oil load, and with the second stage set at 500 psi and the first stage at 4500 psi for 20% oil load or 24% oil load.
  • APV pressure homogenizer Model 15 MR Laboratory Homogenizer from APV Gaulin
  • the term “dispersed phase process” means: an at least 2 step process wherein a starch is sufficiently solubilized; then, in the next or any subsequent process step, the sufficiently solubilized starch is derivatized.
  • starch that is substantially gelatinized so that the starch does not have a Maltese cross when viewed under polarized light and has lost all of its granular or crystalline structure when viewed microscopically at 100 ⁇ magnification.
  • “Sufficiently Solubilized Starch” means starch having an average particle size of less than one micron, as assessed by Polarization Intensity Differential Plus Elastic Light Scattering (Beckman Coulter LS 13 320 Aqueous Model).
  • FIG. 1 depicts an embodiment of a graphical description of the relationship between funnel viscosity and water fluidity, as each is measured according to the conditions described herein.
  • starch is first slurried in an aqueous phase, yielding a slurry of approximately 40% as-is starch solids (approximately 35% dry solids) and then is heated to 54° C. The starch is then acid converted. In one embodiment of the present invention, 0.7% concentrated HCl is added to the slurried starch, the slurry is mixed for 16 hours and is then neutralized to pH 5.5 with 3% NaOH. The starch is then filtered and washed and dried, and then re-suspended to form a slurry of approximately 40% as-is starch solids. In one embodiment, the slurry is then continuously jet cooked at approximately 310° F.
  • the sufficiently solubilized starch is sufficiently derivatized.
  • the sufficiently solubilized waxy maize starch is placed in a constant temperature bath and maintained at 40° C. with constant stirring.
  • the pH is, in one embodiment, adjusted to 7.5 with 3% NaOH.
  • 3% OSA by weight based on the weight of “as-is” starch, was slowly added to the solubilized starch while the pH was maintained at 7.5.
  • the pH is neutralized to 5.5 with dilute HCl.
  • the starch may then be optionally enzyme converted and/or spray-dried.
  • the emulsifier product of the present invention has a water fluidity of no more than 75, and is characterized with the following test oil-in-water emulsion: when the starch half ester of an alkenyl succinic anhydride is used to prepare a test oil-in-water emulsion with the starch as a sole emulsifier at a w/w ratio of the starch:oil of 1:4 and oil load of 12%, the test oil-in-water emulsion is characterized by at least the following: 1. no more than about 5% of oil particles of the test emulsion greater than 1 micron after 24 hours at 57° C. as assessed by polarization intensity differential plus elastic light scattering; and 2. a Brookfield viscosity of the test emulsion of less than about 2000 cps after about one week of storage at 5° C., as assessed by Brookfield Programmable DV-1 Viscometer.
  • Suitable starch sources for the invention may be derived from any native source.
  • a native source as used herein, is one as it is found in nature.
  • GMO genetically modified organisms
  • starch derived from a plant grown from artificial mutations and variations of the above generic composition which may be produced by known standard methods of mutation breeding, are also suitable herein.
  • Typical sources for the starches are cereals (grains), seeds, tubers, roots, legumes and fruits.
  • the native source can be corn (maize), pea, potato, sweet potato, banana, barley, wheat, rice, oat, sago, amaranth, tapioca (cassaya), arrowroot, canna, and sorghum as well as waxy or high amylose varieties thereof.
  • the invention embodied within relates to all starches regardless of amylose content and is intended to include all starch sources, including those which are natural, genetically altered or obtained from hybrid breeding.
  • the starch is a waxy starch and in another embodiment is a waxy corn starch.
  • starch is acid converted.
  • the starch is solubilized.
  • the starch may be solubilized, for example, by chemical, enzymatic or physical processing.
  • the solubilization may result in a converted starch.
  • the conversion may be to any degree so long as the emulsifier product of the present invention does not have a water fluidity greater than 75.
  • Suitable methods for sufficiently solubilizing the starch include, but are not limited to, “jet-cooking,” for example, utilizing a Hydroheater (Hydro-Thermal Corporation, Milwaukee, Wis.) cooking chamber at approximately 154° C. (310° F.); placing the granular starch in boiling water; treating the granular starch with a caustic agent; treating the granular starch with a salt including but not limited to urea; and/or physical destruction of the starch granules.
  • “jet-cooking” for example, utilizing a Hydroheater (Hydro-Thermal Corporation, Milwaukee, Wis.) cooking chamber at approximately 154° C. (310° F.); placing the granular starch in boiling water; treating the granular starch with a caustic agent; treating the granular starch with a salt including but not limited to urea; and/or physical destruction of the starch granules.
  • the solubilized starch is chemically derivatized.
  • the reagent has an alkyl or an alkenyl group which contains at least five carbon atoms or an aralkyl or aralkenyl group which contains at least six carbon atoms, and in one embodiment may contain up to twenty-four carbon atoms.
  • Suitable reagents for sufficiently derivatizing a sufficiently solubilized starch so as to yield a starch half ester of an alkenyl succinic anhydride meeting the criteria outlined above include, but are not limited to, octenyl succinic anhydride, dodecenyl succinic anhydride and various cyclic dicarboxylic acid anhydrides.
  • the reagent is octenyl succinic anhydride or dodecenyl succinic anhydride and in another embodiment is octenyl succinic anhydride.
  • Reagents include without limitation imidazolides, N,N′-disubstituted imidazolium salts of carboxylic or sulfonic acids, quaternary or tertiary amines, acetic anhydride, alkylene oxides, and succinic anhydrides.
  • One or more process steps may be performed between (1) sufficiently solubilizing the starch and (2) sufficiently derivatizing the sufficiently solubilized starch described herein, including but not limited to acid conversion, oxidation, etc., so long as the process steps intervening between the sufficiently solubilizing and sufficiently derivatizing steps outlined above do not render the derivatizing step insufficient in yielding the emulsifier product of the present invention (for example, by further degrading the sufficiently solubilized starch so as to yield an abundance of oligosaccharide degradation byproducts).
  • the solubilized material is treated with phosphoric acid before and/or after the derivatization step.
  • the starch may be converted to reduce the viscosity of the emulsifier product of the present invention.
  • conversion is by acid degradation.
  • conversion is by heat
  • conversion is by shear
  • the conversion may be conducted either before or after the derivatization.
  • the conversion is before derivatization.
  • the conversion may be to any degree so long as the emulsifier product of the present invention does not have a water fluidity greater than 75.
  • the starch is not intentionally converted.
  • the starch may be treated with any enzyme at any time subsequent to derivatization of the solubilized starch or with an enzyme (such as alpha amylase) that randomly cleaves ⁇ (1-4) glycosidic linkages prior to derivatization of the starch.
  • Enzymes useful for treatment after derivatization would include but are not limited to alpha-amylase, beta-amylase, glucoamylase, maltogenase, pullulanase, exo-alpha-1,4-glucosidase, exo-1,4-alpha-D-glucan maltotetrahydrolase, and exo-1,4-alpha-D glucan maltohexahydrolase.
  • the starch may be further treated by enzyme after the starch has been solubilized and derivatized.
  • the enzyme When the desired conversion is reached, the enzyme may be deactivated by heat or pH. Thereafter the pH may be readjusted. The type and concentration of the enzyme, the conversion conditions, and the length of conversion all will contribute to the composition of the resultant product.
  • a combination of enzymes may be used.
  • the starch may be enzyme converted at any time so long as the emulsifier product of the present invention is still capable of sufficient derivatization so as to effectively function as an emulsifier with respect to the above-identified test emulsion.
  • the pH of the derivatized starch may be adjusted to the desired pH according to its intended end use.
  • the pH is adjusted to from 5.0 to 7.5, and in another embodiment from 6.0 to 7.0, using techniques known in the art.
  • the starch may be purified to remove impurities, by-products, off-flavors and colors by methods known in the art including without limitation by washing, dialysis, filtration, ion exchange processes, steam stripping, bleaching such as by chlorites, and/or centrifugation. Such purification may be done at any time in the process as long as the purification does not adversely affect the requirements of the starch emulsifier.
  • the derivatized starch may be used as is in its liquid form or it may be dried using methods known in the art including without limitation drum drying, spray drying, freeze drying, and/or air drying.
  • any of the above process steps may be used individually and/or in combination with any optional steps such as conversion by acid, heat, shear, oxidation, bleaching, enzyme treatment, and/or any combination thereof.
  • any method or combination of methods must result in an emulsifier product of the present invention with a water fluidity of no greater than 75 and characterized in the following test oil-in-water emulsion:
  • test oil-in-water emulsion when the starch half ester of an alkenyl succinic anhydride is used to prepare a test oil-in-water emulsion with the starch as a sole emulsifier at a w/w ratio of the starch:oil of 1:4 and an oil load of 20%, the test oil-in-water emulsion is characterized by at least the following:
  • the water fluidity of the emulsifier product is not greater than 75. In one embodiment the emulsifier product of the present invention has a water fluidity of not greater than 65, and in yet another embodiment the emulsifier product of the present invention has a water fluidity of not greater than 40.
  • the emulsifier product of the present invention has a water fluidity of between 11-20 WF, in another embodiment the emulsifier product of the present invention has a water fluidity of between 11-40, in yet another embodiment the emulsifier product of the present invention has a water fluidity of between 11-65, in a further embodiment the emulsifier product of the present invention has a water fluidity of between 20-40, in a still further embodiment the emulsifier product of the present invention has a water fluidity of between 20-65, and in yet one further embodiment the emulsifier product of the present invention has a water fluidity of between 40-65.
  • the emulsifier product may be used to prepare an oil-in-water emulsion by mixing it with an oil.
  • the oil may include an oil-based active agent including without limitation flavors, colors, fragrances, pharmaceuticals and/or vitamins. Oil is also intended to include triglycerides such as medium chain triglycerides.
  • the oil may be present in the emulsion in any desirable amount possible and the oil load will depend upon many parameters, but specifically upon the amount of emulsifier starch product used. In one embodiment the oil load is 12%, in another embodiment 20%, and in yet another embodiment 24% by weight of the emulsion.
  • the starch:oil ratio of the emulsion may also be any desirable ratio and will also depend upon many parameters.
  • the starch:oil ratio is 1:1, in another embodiment 1:3, in yet another embodiment 1:4 and in still yet another embodiment 1:6, all on a weight:weight basis.
  • an antioxidizing agent is added to the dispersed (oil) phase.
  • a pre-emulsion is prepared prior to the emulsion.
  • the emulsion may also be made into an encapsulated form by techniques known in the art including but not limited to spray drying, extruding, and spray chilling.
  • the encapsulated product may be effectively stored as a powder and spontaneously releases the encapsulant upon exposure to significant moisture, such as when added to water.
  • the emulsion or encapsulated product may be used at any level desired in a variety of products.
  • the products include without limitation food and beverage products, pharmaceuticals, nutraceuticals, infant products, paper products, animal care products, household products, agricultural products, and personal care products.
  • Food and beverage products include, but are not limited to juice beverages, sodas; instant coffees and teas; sauce and gravies; soups; cereals; dressings; bakery products; instant and cook-up mixes; nondairy creamers; salad dressings; and sweetened condensed creamers.
  • Personal care products include without limitation antiperspirants, deodorants, soaps, fragrances, and cosmetics; hair care products, such as hair sprays, mousses, shampoos, cream rinses, bath products, and gels.
  • Paper products include without limitation diapers, sanitary napkins, paper towels, tissues, and toilet tissues.
  • Animal care products include without limitation animal foods and kitty litter.
  • Household products include without limitation cleaners, detergents, fabric softeners, and air fresheners.
  • Flavor Oil 12%-24% Stabilizer 2%-12% Sodium Benzoate 0.15% Citric Acid 0.30% Water Up to 100% The required amounts of sodium benzoate were dissolved in water. Citric acid was dissolved in the above solution. Starch was dispersed with moderate agitation. A pre-emulsion and then an emulsion was made using the procedure set forth for a test oil-in-water emulsion.
  • Emulsion particle sizes were measured using the LS 13 230, manufactured by Beckman Coulter and incorporating Polarization Intensity Differential Screening technology together with a sophisticated software package to provide a dynamic range of particle size measurement capabilities between 0.04 um to 2000 um.
  • sample ID From the pull down manual of the software, we entered sample ID and selected the appropriate optical module to be used for the system to be measured. A sequence of steps automatically followed: Measuring offsets; Alignment; Background measurement; Measure loading. The instrument sounded a bell and displayed Measuring Loading when ready to accept a sample.
  • a diluted sample was introduced by drops into the sample reservoir and changes in the Measure Loading were observed. This function measured the amount of light scattered out of the beam by the particles so as to determine an appropriate concentration of sample. When sizing particles without using PIDS an obscuration level of 8% to 12% is appropriate. When PIDS is used, a PIDS obscuration of 40% to 60% is recommended. A real part of index of refraction of 1.5 was used.
  • the pull-down menu allowed the user to print the results and related graphs either to the inline printer or to a PDF file.
  • Viscosity measurements were performed with the Brookfield Programmable DV-I Viscometer at a given measurement conditions (spindle S63@60 rpm with a reading taken 15 seconds after the start of rotation).
  • the principal of operation of the DV-I is to drive or rotate a spindle (which is immersed in the test fluid) through a calibrated spring.
  • the viscous drag of the fluid against the spindle is measured by the spring deflection.
  • Spring deflection is measured with a rotary transducer which translates the drag into viscosity of the test fluid through an internal calibration.
  • the measurement range (in centipoises or milliPascal seconds) is determined by the rotational speed of the spindle, the size and shape of the spindle, the container the spindle is rotating in, and the full scale torque of the calibrated spring. Viscosity measurements were made on a 22° C. sample contained in an 8 ounce tall glass fluid container having dimensions of 2.25′′ width ⁇ 5′′ height. The Viscometer was leveled and warmed up for ⁇ 10 minutes. The selected spindle was rotated through the sample of interest for a predetermined time period (15 seconds). The viscosity of the test fluid was displayed in centipoises.
  • N3700 NATIONAL® 3700 starch
  • PG 2000 PURITY® GUM 2000 starch
  • PG 1773 PURITY® GUM 1773 starch (all three starches are commercially available from National Starch LLC, Bridgewater, N.J.).
  • ETENIATM is a trademark of and is commercially available from AVEBE, Veendm, the Netherlands).
  • High oil load (24%) performance of emulsifiers of the invention prepared using various OSA-derivatized dispersed phase emulsifiers derived from various starch sources and subject to high oil load (24%) emulsion conditions were assessed.
  • Samples were prepared by slurrying 8 kg (anhydrous basis) starch in 12 liters tap water. This slurry was then jet cooked, using a Hydroheater (Hydro-Thermal Corporation, Milwaukee, Wis.) cooking chamber at approximately 154° C. (310° F.), resulting in a 30% solids jet cooked starch dispersion (after slight dilution—one waxy corn starch cook was run at 24.5% solids).
  • Hydroheater Hydroheater
  • the cook was divided into three 8 liter stainless steel beakers, and placed in a hot water bath at 90° C. To each was added 0.075% concentrated HCl (on as-is starch weight). The funnel viscosity was tracked over time until the desired range was reached.
  • the OSA derivatization reaction was carried out on these dispersions in stainless steel beakers placed in an immersion circulator bath to maintain the temperature at 55° C. (waxy corn reactions were run at 59 and 76° C.). The pH of each was adjusted to 7.5 with 3% NaOH. Then 2.5% OSA reagent (1.75% for sample 2)(2.5% OSA reagent is equivalent to 2.84% OSA (dry basis) on dry starch) on as-is starch weight was added drop-wise to each dispersion while the pH was maintained at 7.5, using 3% NaOH. When no 3% NaOH was needed to keep the pH at 7.5 for a 30 minute period (indicating that the OSA reaction with starch was completed), the dispersion was then adjusted to pH 5.8 with dilute HCl. The product was then spray-dried.
  • TABLE 2 depicts characteristics of various examples of emulsions prepared utilizing emulsifier products of the present invention, These examples include emulsifier products of the present invention derived from a variety of starch sources, including waxy corn starch.
  • Starch-to-oil ratio of the various test emulsions described in TABLE 2 may be derived by dividing the “% starch solids” indicated for each emulsion by the oil load of 24%.
  • WAXIPRO® is a registered trademark denoting a product sold by National Starch, LLC, Bridgewater, N.J.
  • Sample 2 (Waxy Corn) was prepared by utilizing an acid-converted waxy corn starch that was re-suspended, jet cooked, reacted with 2.5% OSA in the dispersed phase, neutralized to pH 6.03 and spray dried.
  • Waxy 30% SS, 2.84 13.49 6 0.214 0.198 0 0.302 0.289 0 0.348 0.327 0 Potato pH 7, 55° C. 4.
  • Waxy 30% SS, 2.84 28.24 5 0.244 0.224 0 0.283 0.268 0 0.312 0.294 0 Potato pH 7, 55° C. 5.
  • This example illustrates the preparation of an enzyme-converted starch of the invention for use in beverage flavor emulsification.
  • An OSA-derivatized dispersed phase emulsifier was prepared by first slurrying waxy maize starch at 40% as-is solids in tap water and adding 0.25% phosphoric acid on starch weight to the slurry. This slurry was then jet cooked at approximately 310° F. (154° C.), resulting in a solubilized starch dispersion with dry solids of 30%. Thereafter, the solubilized starch dispersion was placed in a constant temperature bath and maintained at 40° C. with constant stirring.
  • OSA reagent on as-is starch weight was added drop-wise over a 2 hour period to the solubilized starch so as to derivatize the solubilized starch.
  • the pH was maintained at 7.5, using 3% NaOH.
  • the dispersion was then adjusted to pH 5.5 with dilute HCl.
  • the degree of starch degradation by ⁇ -amylase was correlated to the loss in viscosity.
  • the desired enzyme reaction end point was reached with a funnel viscosity of 12.7 seconds (measured at 19% solids instead of 8.5% solids, as this product was low in viscosity).
  • the enzyme was deactivated by reducing the pH to 2.7 and holding for 30 min. to denature the enzyme.
  • the sample was then adjusted to pH 4 and spray-dried at an inlet temperature of 200°-210° C. and an outlet temperature of 85°-90° C. using a standard #22 11/4 J nozzle obtained from Spraying Systems Company.
  • This material was prepared identically as per Example 3A, with the exception that 0.3% OPTIMALT® BBA ⁇ -amylase treatment occurred prior to OSA derivatization of the starch.
  • emulsifier products of the present invention made as per Example 3A produced an emulsion that had a mean particle size of 0.835 microns and its emulsion did not separate after 18 hours
  • emulsifiers made as per Example 3B produced an emulsion that had a mean particle size of 11.57 microns and its emulsion showed 15 mL of oil separation after only 2 hours.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Materials Engineering (AREA)
  • Medicinal Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Food Science & Technology (AREA)
  • Nutrition Science (AREA)
  • Dermatology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Biochemistry (AREA)
  • Cosmetics (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Medicinal Preparation (AREA)
  • Grain Derivatives (AREA)
  • General Preparation And Processing Of Foods (AREA)
  • Jellies, Jams, And Syrups (AREA)
  • Colloid Chemistry (AREA)
US12/626,463 2009-11-25 2009-11-25 Alkenyl succinic acid anhydride half ester emulsifier Abandoned US20110124746A1 (en)

Priority Applications (17)

Application Number Priority Date Filing Date Title
US12/626,463 US20110124746A1 (en) 2009-11-25 2009-11-25 Alkenyl succinic acid anhydride half ester emulsifier
US12/687,782 US7829600B1 (en) 2009-11-25 2010-01-14 Alkenyl succinic acid anhydride half ester emulsifier
ZA2010/07836A ZA201007836B (en) 2009-11-25 2010-11-02 Alkenyl succinic acid anhydride half ester emulsifier
AU2010241234A AU2010241234B2 (en) 2009-11-25 2010-11-04 Alkenyl succinic acid anhydride half ester emulsifier
MYPI2010005271 MY150807A (en) 2009-11-25 2010-11-10 Alkenyl succinic acid anhydride half ester emulsifier
MX2010012510A MX2010012510A (es) 2009-11-25 2010-11-16 Emulsionador de semi-ester de anhidrido de acido alquenil succinico.
ARP100104297A AR079113A1 (es) 2009-11-25 2010-11-19 Emulsionante de hemiester de anhidrido de acido alquenil succinico
EP10191815.9A EP2330134B1 (de) 2009-11-25 2010-11-19 Alkenylbernsteinsäure Anhydrid-Halbester
CA2721888A CA2721888C (en) 2009-11-25 2010-11-19 Alkenyl succinic acid anhydride half ester emulsifier
PE2010001075A PE20110518A1 (es) 2009-11-25 2010-11-20 Emulsionante de hemiester de anhidrido de acido alquenil succinico
CL2010001281A CL2010001281A1 (es) 2009-11-25 2010-11-22 Producto emulsionante que comprende un semi-ester de almidon de un anhidrido alquenil succinico, que tiene una fluidez en agua no mayor a 75, que es preparado por un proceso de fase dispersa, y que es utilizado para preparar una emulsion de aceite en agua; y emulsion que comprende un aceite, agua y dicho producto emulsionante.
SG201008661-9A SG171564A1 (en) 2009-11-25 2010-11-24 Alkenyl succinic acid anhydride half ester emulsifier
JP2010261325A JP5912012B2 (ja) 2009-11-25 2010-11-24 無水アルケニルコハク酸ハーフエステル乳化剤
TW099140474A TWI522048B (zh) 2009-11-25 2010-11-24 烯基丁二酸酐半酯乳化劑
RU2010147913/13A RU2528026C2 (ru) 2009-11-25 2010-11-24 Эмульгатор в виде полуэфира ангидрида алкенил-янтарной кислоты
CN201010555820.9A CN102151516B (zh) 2009-11-25 2010-11-25 烯基丁二酸酐半酯乳化剂
BRPI1004713-1A BRPI1004713B1 (pt) 2009-11-25 2010-11-25 Produto emulsificante de meio-éster de amido de anidrido succínico de alquenila e emulsão

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US12/626,463 US20110124746A1 (en) 2009-11-25 2009-11-25 Alkenyl succinic acid anhydride half ester emulsifier

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US12/687,782 Continuation US7829600B1 (en) 2009-11-25 2010-01-14 Alkenyl succinic acid anhydride half ester emulsifier

Publications (1)

Publication Number Publication Date
US20110124746A1 true US20110124746A1 (en) 2011-05-26

Family

ID=43034805

Family Applications (2)

Application Number Title Priority Date Filing Date
US12/626,463 Abandoned US20110124746A1 (en) 2009-11-25 2009-11-25 Alkenyl succinic acid anhydride half ester emulsifier
US12/687,782 Active US7829600B1 (en) 2009-11-25 2010-01-14 Alkenyl succinic acid anhydride half ester emulsifier

Family Applications After (1)

Application Number Title Priority Date Filing Date
US12/687,782 Active US7829600B1 (en) 2009-11-25 2010-01-14 Alkenyl succinic acid anhydride half ester emulsifier

Country Status (16)

Country Link
US (2) US20110124746A1 (de)
EP (1) EP2330134B1 (de)
JP (1) JP5912012B2 (de)
CN (1) CN102151516B (de)
AR (1) AR079113A1 (de)
AU (1) AU2010241234B2 (de)
BR (1) BRPI1004713B1 (de)
CA (1) CA2721888C (de)
CL (1) CL2010001281A1 (de)
MX (1) MX2010012510A (de)
MY (1) MY150807A (de)
PE (1) PE20110518A1 (de)
RU (1) RU2528026C2 (de)
SG (1) SG171564A1 (de)
TW (1) TWI522048B (de)
ZA (1) ZA201007836B (de)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110082290A1 (en) * 2009-10-07 2011-04-07 Akzo Nobel Chemicals International B.V. Superhydrophilic amphiphilic copolymers and processes for making the same
US8962092B2 (en) 2013-01-30 2015-02-24 Corn Products Development, Inc. Paper sizing using an agent containing uniformly bound octenyl succinic anhydride groups made by the reaction of octenyl succinic anhydride onto a dispersed waxy starch
WO2021222519A1 (en) * 2020-04-30 2021-11-04 Kansas State University Research Foundation Encapsulated compositions and use of octenylsuccinic anhydride starch as emulsifying agent
US11173106B2 (en) 2009-10-07 2021-11-16 Johnson & Johnson Consumer Inc. Compositions comprising a superhydrophilic amphiphilic copolymer and a micellar thickener

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8258250B2 (en) 2009-10-07 2012-09-04 Johnson & Johnson Consumer Companies, Inc. Compositions comprising superhydrophilic amphiphilic copolymers and methods of use thereof
JP6082933B2 (ja) * 2010-09-14 2017-02-22 学校法人神奈川大学 乳化剤及びその製造方法、並びに乳化物の製造方法
WO2012082065A1 (en) 2010-12-15 2012-06-21 Speximo Ab New particle stabilized emulsions and foams
CN102550896B (zh) * 2011-12-13 2014-06-18 江南大学 一种抗消化淀粉基乳化剂及其应用
JP5843691B2 (ja) * 2012-05-11 2016-01-13 キヤノン株式会社 情報処理装置、印刷システム、情報処理装置の制御方法、およびコンピュータプログラム
WO2014099946A1 (en) * 2012-12-19 2014-06-26 Johnson & Johnson Consumer Companies, Inc. Anhydrous powder-to-liquid particles
BR112016029317A2 (pt) 2014-06-16 2017-08-22 Johnson & Johnson Consumer Inc composições e métodos para melhorar a aplicação tópica de um cosmético colorido
KR101964278B1 (ko) 2015-11-24 2019-04-01 주식회사 엘지화학 딥 성형용 라텍스 조성물 및 이로부터 제조된 딥 성형품
CN106812019B (zh) * 2015-11-30 2018-11-09 艺康美国股份有限公司 剥离助剂
DK3544441T3 (da) 2016-11-28 2021-06-07 Corn Products Dev Inc Stivelsesbaserede tekstureringsmidler til fødevaresammensætninger
US11382334B2 (en) 2016-11-28 2022-07-12 Corn Products Development, Inc. Starch-based texturizers for low protein yogurt, yogurt composiiton and method of making the yogurt composition
EP3544440A1 (de) 2016-11-28 2019-10-02 Corn Products Development, Inc. Texturgeber auf stärkebasis für proteinarme joghurtzusammensetzungen und verfahren zur herstellung eines proteinarmen joghurts
CN110869395A (zh) * 2017-05-16 2020-03-06 嘉吉公司 含有淀粉转化材料的制品
CN109517080B (zh) * 2018-11-06 2023-06-16 浙江大学 辛烯基琥珀酸淀粉酯、脂溶性营养素微胶囊及制备方法和应用
CN109457004A (zh) * 2018-11-06 2019-03-12 浙江新和成股份有限公司 吸附淀粉、吸附淀粉团聚体及制备方法、应用和营养素制剂
CN109517079B (zh) * 2018-11-06 2020-06-23 浙江新和成股份有限公司 一种制备辛烯基琥珀酸淀粉酯的方法及其应用
CN109485739B (zh) * 2018-11-06 2020-06-23 浙江新和成股份有限公司 一种辛烯基琥珀酸淀粉酯的制备方法
CN113087812B (zh) * 2021-04-23 2022-10-21 宁波工程学院 一种高流动性淀粉的制备方法
EP4279570A1 (de) * 2022-05-19 2023-11-22 The Procter & Gamble Company Verfahren zur herstellung einer partikelförmigen wäschewaschmittelzusammensetzung

Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2661349A (en) * 1949-02-18 1953-12-01 Nat Starch Products Inc Polysaccharide derivatives of substituted dicarboxylic acids
US3432207A (en) * 1967-01-25 1969-03-11 Kelsey Hayes Co Wheel and method of manufacturing the same
US3455838A (en) * 1966-04-22 1969-07-15 Nat Starch Chem Corp Method of encapsulating water-insoluble substances and product thereof
US4460617A (en) * 1982-06-04 1984-07-17 National Starch And Chemical Corp. Protein-free coffee whitener and method of making same
US4845152A (en) * 1986-05-12 1989-07-04 National Starch And Chemical Corporation Tape joint compounds utilizing starch stabilized emulsions as binders
US4977252A (en) * 1988-03-11 1990-12-11 National Starch And Chemical Investment Holding Corporation Modified starch emulsifier characterized by shelf stability
US5185176A (en) * 1988-03-11 1993-02-09 National Starch And Chemical Investment Holding Corporation Food products containing modified starch emulsifier
US5354559A (en) * 1990-05-29 1994-10-11 Grain Processing Corporation Encapsulation with starch hydrolyzate acid esters
US5616358A (en) * 1995-07-19 1997-04-01 The Procter & Gamble Company Stable beverages containing emulsion with unweighted oil and process of making
US6372361B1 (en) * 2000-07-07 2002-04-16 National Starch And Chemical Investment Holding Corporation Coating for paper products
US20020142087A1 (en) * 2001-03-19 2002-10-03 Trubiano Paolo C. Substantially sediment-free beverage emulsion stabilizer
US6809197B1 (en) * 2003-06-11 2004-10-26 Mgp Ingredients, Inc. Emulsion stabilizing starch products
US20050208009A1 (en) * 2004-03-22 2005-09-22 Valerie Bonnardel Emulsifier
US7157573B2 (en) * 1999-01-15 2007-01-02 Cooperatie Avebe U.A. Hydrophobic starch derivatives

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2461139A (en) 1945-01-08 1949-02-08 Nat Starch Products Inc Starch ester derivatives and method of making same
US3732207A (en) 1971-01-29 1973-05-08 Anheuser Busch Preparation of dextrins and starch esters
JP2540204B2 (ja) * 1988-08-18 1996-10-02 ナシヨナル・スターチ・アンド・ケミカル・コーポレイション 保存安定性を有する化工でんぷん乳化剤
GB9106569D0 (en) * 1991-03-27 1991-05-15 Cerestar Holding Bv Starch esters
JP3825510B2 (ja) * 1996-10-07 2006-09-27 三菱化学株式会社 蔗糖脂肪酸エステル水溶液の粘度低下剤
WO2001016348A1 (en) 1999-09-01 2001-03-08 Novozymes A/S Maltogenic amylase-modified starch derivatives
CN1152737C (zh) * 2001-01-05 2004-06-09 中国石油化工股份有限公司 一种金属加工用乳化油乳化剂及乳化油组合物
US6455512B1 (en) * 2001-03-05 2002-09-24 Tic Gums, Inc. Water-soluble esterified hydrocolloids
US8252322B2 (en) * 2003-06-03 2012-08-28 Corn Products Development, Inc. Delivery system with increased bioavailability
RU2275029C2 (ru) * 2004-05-17 2006-04-27 Научно-консультационный Центр Состав пищевого продукта на вафельной основе (варианты)
ES2625898T3 (es) 2005-07-12 2017-07-20 Coöperatie Avebe U.A. Emulsionante
EP1880616A1 (de) * 2006-07-18 2008-01-23 Stichting Top Institute Food and Nutrition Amylase-induzierte sensorische Wirkung von Emulsionen mit geringem Fettgehalt enthaltender hydrophober Stärke als Emulgator

Patent Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2661349A (en) * 1949-02-18 1953-12-01 Nat Starch Products Inc Polysaccharide derivatives of substituted dicarboxylic acids
US3455838A (en) * 1966-04-22 1969-07-15 Nat Starch Chem Corp Method of encapsulating water-insoluble substances and product thereof
US3432207A (en) * 1967-01-25 1969-03-11 Kelsey Hayes Co Wheel and method of manufacturing the same
US4460617A (en) * 1982-06-04 1984-07-17 National Starch And Chemical Corp. Protein-free coffee whitener and method of making same
US4845152A (en) * 1986-05-12 1989-07-04 National Starch And Chemical Corporation Tape joint compounds utilizing starch stabilized emulsions as binders
US5185176A (en) * 1988-03-11 1993-02-09 National Starch And Chemical Investment Holding Corporation Food products containing modified starch emulsifier
US4977252A (en) * 1988-03-11 1990-12-11 National Starch And Chemical Investment Holding Corporation Modified starch emulsifier characterized by shelf stability
US5354559A (en) * 1990-05-29 1994-10-11 Grain Processing Corporation Encapsulation with starch hydrolyzate acid esters
US5616358A (en) * 1995-07-19 1997-04-01 The Procter & Gamble Company Stable beverages containing emulsion with unweighted oil and process of making
US7157573B2 (en) * 1999-01-15 2007-01-02 Cooperatie Avebe U.A. Hydrophobic starch derivatives
US6372361B1 (en) * 2000-07-07 2002-04-16 National Starch And Chemical Investment Holding Corporation Coating for paper products
US20020142087A1 (en) * 2001-03-19 2002-10-03 Trubiano Paolo C. Substantially sediment-free beverage emulsion stabilizer
US6809197B1 (en) * 2003-06-11 2004-10-26 Mgp Ingredients, Inc. Emulsion stabilizing starch products
US20050208009A1 (en) * 2004-03-22 2005-09-22 Valerie Bonnardel Emulsifier

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110082290A1 (en) * 2009-10-07 2011-04-07 Akzo Nobel Chemicals International B.V. Superhydrophilic amphiphilic copolymers and processes for making the same
US8399590B2 (en) * 2009-10-07 2013-03-19 Akzo Nobel Chemicals International B.V. Superhydrophilic amphiphilic copolymers and processes for making the same
US9243074B2 (en) 2009-10-07 2016-01-26 Akzo Nobel Chemicals International B.V. Superhydrophilic amphiphilic copolymers and processes for making the same
US11173106B2 (en) 2009-10-07 2021-11-16 Johnson & Johnson Consumer Inc. Compositions comprising a superhydrophilic amphiphilic copolymer and a micellar thickener
US8962092B2 (en) 2013-01-30 2015-02-24 Corn Products Development, Inc. Paper sizing using an agent containing uniformly bound octenyl succinic anhydride groups made by the reaction of octenyl succinic anhydride onto a dispersed waxy starch
WO2021222519A1 (en) * 2020-04-30 2021-11-04 Kansas State University Research Foundation Encapsulated compositions and use of octenylsuccinic anhydride starch as emulsifying agent

Also Published As

Publication number Publication date
ZA201007836B (en) 2011-07-27
AU2010241234B2 (en) 2014-04-17
AR079113A1 (es) 2011-12-28
JP2011110554A (ja) 2011-06-09
CL2010001281A1 (es) 2011-03-11
PE20110518A1 (es) 2011-08-11
BRPI1004713B1 (pt) 2018-02-27
CA2721888A1 (en) 2011-05-25
TW201136530A (en) 2011-11-01
CN102151516A (zh) 2011-08-17
CA2721888C (en) 2017-07-04
MY150807A (en) 2014-02-28
CN102151516B (zh) 2015-11-18
BRPI1004713A2 (pt) 2013-03-12
TWI522048B (zh) 2016-02-21
AU2010241234A1 (en) 2011-06-09
JP5912012B2 (ja) 2016-04-27
RU2528026C2 (ru) 2014-09-10
US7829600B1 (en) 2010-11-09
MX2010012510A (es) 2011-05-24
EP2330134B1 (de) 2018-12-19
EP2330134A1 (de) 2011-06-08
RU2010147913A (ru) 2012-05-27
SG171564A1 (en) 2011-06-29

Similar Documents

Publication Publication Date Title
US7829600B1 (en) Alkenyl succinic acid anhydride half ester emulsifier
EP1584370B1 (de) Emulgator
EP1586371B1 (de) Einkapseln von sauerstoffempfindlichen Mitteln
EP2556093B1 (de) Verfahren zur stärkemodifizierung
CN103865080A (zh) 具有改进性质的羧甲基纤维素
JP5762961B2 (ja) アルテルナン誘導体
JP6978941B2 (ja) エマルジョン安定化剤としてのバイオポリマーブレンド
Halahlah et al. Wood hemicelluloses as innovative wall materials for spray-dried microencapsulation of berry juice: Part 1—effect of homogenization techniques on their feed solution properties
JP2021181088A (ja) エマルジョン安定化剤としてのバイオポリマーブレンド
US20240043570A1 (en) Modified starches for home care and personal care

Legal Events

Date Code Title Description
AS Assignment

Owner name: BRUNOB II B.V., NETHERLANDS

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:TRKSAK, RALPH;MAKARIOUS, AFAF;REEL/FRAME:024983/0740

Effective date: 20100908

Owner name: NATIONAL STARCH LLC, NEW JERSEY

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:TRKSAK, RALPH;MAKARIOUS, AFAF;REEL/FRAME:024983/0740

Effective date: 20100908

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION