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US3915736A - Composite maltitol powder - Google Patents

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Publication number
US3915736A
US3915736A US485237A US48523774A US3915736A US 3915736 A US3915736 A US 3915736A US 485237 A US485237 A US 485237A US 48523774 A US48523774 A US 48523774A US 3915736 A US3915736 A US 3915736A
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particles
sugar alcohol
maltitol
core particles
diameter
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US485237A
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Koichi Oyamada
Seiji Hashimoto
Kazuaki Kuno
Yasubumi Hirabayashi
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Nikken Chemicals Co Ltd
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Nikken Chemicals Co Ltd
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    • 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
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/33—Artificial sweetening agents containing sugars or derivatives
    • A23L27/34—Sugar alcohols

Definitions

  • maltitol is a sugar alcohol having a sweet taste similar to that of sucrose. Recently, it has been found that maltitol is not absorbed by the digestive organs, and hence is important as a low calorie sweetening material. However, maltitol is difficult to crystallize and is highly hygroscopic, and therefore is difficult to use in powdered form. When maltitol or a maltitol-containing powder is exposed to the air, the powder immediately absorbs moisture, cakes and then forms a solution by dissolving in the water absorbed. Accordingly, the applications of maltitol have been quite limited even though maltitol has ideal characteristics as a lowcalorie sweetening material.
  • Another object of the invention is to provide a process for imparting low caking properties to maltitol powder.
  • the caking tendency of maltitol powder is reduced by coating the surface of the maltitol particles with fine low hygroscopic sugar alcohol particles.
  • the low caking maltitol powder of the invention is composed of core particles containing mainly maltitol and fine low caking sugar alcohol particles, which fine particles are bonded to the surface of the molten core particles.
  • the core particles may be pure maltitol, but usually contain more than 50 wt 7a, preferably more than 70 wt 7c maltitol, and another ingredient, such as sorbitol, hydrogenated oligosaccharides, hydrogenated dextrin, which lower the cost of the particles.
  • sorbitol hydrogenated oligosaccharides
  • hydrogenated dextrin hydrogenated dextrin
  • Suitable low hygroscopic sugar alcohols include sorbitol, mannitol, xylitol and hydrogenated dry starch syrup solids.
  • Other sweetening materials e.g., saccharin or the like, may be combined with the maltitol core particles or the fine sugar alcohol particles.
  • Core particles of l50 mesh that is l004000p. diameter, may be used, however, core particles having a diameter of 4001 700p. are preferable because of ease of preparation and use of the particles.
  • the diameter of the fine low hygroscopic sugar alcohol particles is preferably less than one-third, most preferably less than one-fifth, that of the core particles. Accordingly, 100 mesh low hygroscopic sugar alcohol particles are preferable, and those having a diameter of 10-170;!- are most preferable. When the ratio of the fine low hygroscopic sugar alcohol particles to the core particles is too high, the low calorie characteristic of the product will be lost.
  • a suitable ratio of fine sugar alcohol particles is usually l0l00 wt parts, preferably 15-55 wt parts, to 100 wt. parts of core particles.
  • the low caking composite maltitol powder of the invention is composed of l00 wt. parts of core particles containing more than 50%, preferably more than maltitol and having a diameter of l004000p., preferably 400-1 700;.:., and 10-100 wt. parts of fine low hygroscopic sugar alcohol particles having a diameter less than 170a, preferably 40-170u, coated onto the surface of the molten core particles.
  • the low caking composite maltitol powder may be prepared by mixing the core particles with the fine sugar alcohol particles in a mixer with heating, coating the fine sugar alcohol particles onto the surface of the molten core particles, and cooling the mixture to bond the fine sugar alcohol particles to the core particles. More particularly, a solution of maltitol containing more than 50%, preferably more than 70% total solid components is heated and condensed to give a molten product containing substantially no water. The molten product is cooled to form a block, is crushed in a dry atmosphere and is sifted to give core particles having a diameter of -4000,11, preferably 400l700p..
  • the low hygroscopic sugar alcohol such as sorbitol, mannitol or the like, is crushed, sifted and dried to give fine sugar alcohol particles having a diameter less than l70/.L, preferably 40170,u..
  • a suitable amount of the maltitol core particles and the fine sugar alcohol particles are placed in a mixer, and are gradually heated with stirring.
  • the ratio of the fine sugar alcohol particles is in the range of 30-100 wt parts, preferably 40-100 wt parts, to 100 wt parts of the maltitol core particles.
  • the temperature used for the heating is dependent upon the type of low hygroscopic sugar alcohol, and is preferably lower than the softening temperatures of the sugar alcohol. In order to increase the amount of fine sugar alcohol particles coated onto the core particles, a relatively high temperature should be selected. Conversely, to decrease the amount of fine sugar alcohol particles coated onto the core particles, a relatively low temperature should be selected.
  • the temperature is usually 4095 C, preferably 6080C.
  • the mixture of particles is heated to the predetermined temperature and is continuously stirred at that temperature until the fine sugar alcohol particles are uniformly coated onto the surface of the molten core particles.
  • the time required for the coating is dependent upon the temperature of the mixture of particles. and is usually in the range of 30-120 minutes.
  • the stirring velocity is selected so as to give uniform and suffi cient contact of the fine sugar alcohol particles with the maltitol core particles.
  • the heating is stopped at this stage, and the mixture is cooled and sifted to separate excess of fine sugar alcohol particles and give the composite maltitol powder. Excess fine sugar alcohol particles can be separated by sifting and can be recycled.
  • Suitable mixers used in the process of the invention include conventional fixed vessel mixers, rotary vessel mixers, and other mixers used for mixing and blending solid particles.
  • a mixer whose inner temperature can be controlled is preferable.
  • Suitable mixers include rotary cylindrical mixers, jacket cylindrical mixers, and the like.
  • the low caking composite maltitol powder will not cake when kept in air having a relative humidity of 59% and temperature of 37C for 2 hours. On the other hand, conventional powders containing maltitol will cake within several minutes.
  • EXAMPLE 1 A 750 kg portion of an aqueous solution containing 75% solid component composed mainly of maltitol (75% maltitol, 57r sorbitol and 20% of a hydrogenated oligosaccharide higher than a trisaccharide alcohol) was condensed in a vacuum of 740750 mm Hg at a maximum temperature of l l5C, to form a concentrate containing substantially no water. The concentrate was cooled, crushed with a hammer crusher and was sifted in air having a relative humidity of 40%, to obtain -30 mesh particles (SOD-1700a). A 200 kg amount of the resulting core particles containing maltitol and 40 kg of fine sorbitol particles of diameter less than 100p.
  • EXAMPLE 2 A 200 kg portion of the maltitol core particles of Example and 100 kg of fine particles of hydrogenated starch syrup solids (passed through a 150 mesh sieve; less than 100p. diameter) were placed in a I000 liter horizontal cylindrical mixer equipped with a jacket. The mixture was heated at 75C with stirring at a rate of 10 rpm. for 60 minutes. and then was cooled and sifted to give 240 kg of the composite maltitol powder.
  • the composite powder had an angle of repose of 36, and contained 20 wt parts of hydrogenated starch syrup solids per wt parts of core particles. Even though the composite powder was kept for more than 2 hours in an atmosphere with a relative humidity of 59%, at 37C, the fluidity of the composite powder did not decrease, and the composite powder did not cake.
  • a low caking composite maltitol powder which comprises:
  • core particles containing more than 50% by weight of maltitol and a coating of fine low hygroscopic sugar alcohol particles having a diameter less than onethird of the diameter of the core particles.
  • a process for preparing a low caking composite maltitol which comprises: mixing 100 wt parts of core particles containing more than 50% by weight of maltitol and having a diameter of 100-4000p., with 10-200 wt. parts of fine sugar alcohol particles with a diameter less than one-third that of the core particles, heating the mixture with stirring at a temperature of 4095C to coat the fine sugar alcohol particles onto the surface of the core particles, and cooling the product mixture.
  • sugar alcohol is selected from the group consisting of sorbitol, mannitol, xylitol and hydrogenated starch syrup solids.

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  • Life Sciences & Earth Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Saccharide Compounds (AREA)
  • Seasonings (AREA)
  • Medicinal Preparation (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)

Abstract

A composite maltitol powder is prepared from core particles containing more than 50% maltitol coated with fine low hygroscopic sugar alcohol particles having a diameter less than one-half the diameter of the core particles.

Description

Unite States Patent Oyamada et al.
Oct. 28, 1975 COMPOSITE MALTITOL POWDER Inventors: Koichi Oyamada, Tokyo; Seiji Hashimoto, Omiya; Kazuaki Kuno, Sowa; Yasubumi Hirabayashi, Kawasaki, all of Japan Nikken Checicals (30., Ltd., Tokyo, Japan Filed: July 2, 1974 Appl. No.: 485,237
Assignee:
Foreign Application Priority Data July 7, 1973 Japan 48-76786 US. Cl. 127/29; 127/63; 426/213; 426/217; 426/285; 427/180; 427/212 Int. Cl. A23L 1/236; Cl3F 3/00 Field of Search 127/29, 30, 63; 426/213, 426/217 References Cited UNITED STATES PATENTS 3/1972 Conrad 426/217 3,656,973 4/1972 Paterson 426/217 OTHER PUBLICATIONS Chemical Abstracts, 76: 27l4d (1972).
Chemical Abstracts, 77: 998931 (1972).
Chemical Abstracts, 80: 694l0c (1974).
Primary ExaminerMorris O. Wolk Assistant Examiner-Sidney Marantz Attorney, Agent, or Firm-Oblon, Fisher, Spivak, McClelland & Maier 8 Claims, N0 Drawings COMPOSITE MALTITOL POWDER BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a low caking composite maltitol powder composed of core particles of maltitol coated with fine sugar alcohol particles, and the manufacture thereof.
2. Description of the Prior Art Maltitol is a sugar alcohol having a sweet taste similar to that of sucrose. Recently, it has been found that maltitol is not absorbed by the digestive organs, and hence is important as a low calorie sweetening material. However, maltitol is difficult to crystallize and is highly hygroscopic, and therefore is difficult to use in powdered form. When maltitol or a maltitol-containing powder is exposed to the air, the powder immediately absorbs moisture, cakes and then forms a solution by dissolving in the water absorbed. Accordingly, the applications of maltitol have been quite limited even though maltitol has ideal characteristics as a lowcalorie sweetening material.
A need exists therefore for a maltitol powder which will resist caking when exposed to the air.
SUMMARY OF THE INVENTION Accordingly, one object of the present invention is to provide a low caking composite maltitol powder.
Another object of the invention is to provide a process for imparting low caking properties to maltitol powder.
These and other objects of the invention as will hereinafter become more readily understood can be attained by a powder of core particles containing more than 50% by weight maltitol coated with fine low hygroscopic sugar alcohol particles on the surface of the core particles.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS In accordance with the invention, the caking tendency of maltitol powder is reduced by coating the surface of the maltitol particles with fine low hygroscopic sugar alcohol particles.
The low caking maltitol powder of the invention is composed of core particles containing mainly maltitol and fine low caking sugar alcohol particles, which fine particles are bonded to the surface of the molten core particles.
The core particles may be pure maltitol, but usually contain more than 50 wt 7a, preferably more than 70 wt 7c maltitol, and another ingredient, such as sorbitol, hydrogenated oligosaccharides, hydrogenated dextrin, which lower the cost of the particles. When the content of maltitol in the core particles is less than 50 wt the low calorie characteristic of the product will be disadvantageously lost.
Suitable low hygroscopic sugar alcohols include sorbitol, mannitol, xylitol and hydrogenated dry starch syrup solids. Other sweetening materials, e.g., saccharin or the like, may be combined with the maltitol core particles or the fine sugar alcohol particles.
Core particles of l50 mesh, that is l004000p. diameter, may be used, however, core particles having a diameter of 4001 700p. are preferable because of ease of preparation and use of the particles. The diameter of the fine low hygroscopic sugar alcohol particles is preferably less than one-third, most preferably less than one-fifth, that of the core particles. Accordingly, 100 mesh low hygroscopic sugar alcohol particles are preferable, and those having a diameter of 10-170;!- are most preferable. When the ratio of the fine low hygroscopic sugar alcohol particles to the core particles is too high, the low calorie characteristic of the product will be lost. On the other hand, when the ratio is too low, the sugar particles will be present in insufficient amounts to prevent caking of the maltitol. Accordingly, a suitable ratio of fine sugar alcohol particles is usually l0l00 wt parts, preferably 15-55 wt parts, to 100 wt. parts of core particles.
The low caking composite maltitol powder of the invention is composed of l00 wt. parts of core particles containing more than 50%, preferably more than maltitol and having a diameter of l004000p., preferably 400-1 700;.:., and 10-100 wt. parts of fine low hygroscopic sugar alcohol particles having a diameter less than 170a, preferably 40-170u, coated onto the surface of the molten core particles.
The low caking composite maltitol powder may be prepared by mixing the core particles with the fine sugar alcohol particles in a mixer with heating, coating the fine sugar alcohol particles onto the surface of the molten core particles, and cooling the mixture to bond the fine sugar alcohol particles to the core particles. More particularly, a solution of maltitol containing more than 50%, preferably more than 70% total solid components is heated and condensed to give a molten product containing substantially no water. The molten product is cooled to form a block, is crushed in a dry atmosphere and is sifted to give core particles having a diameter of -4000,11, preferably 400l700p.. The low hygroscopic sugar alcohol, such as sorbitol, mannitol or the like, is crushed, sifted and dried to give fine sugar alcohol particles having a diameter less than l70/.L, preferably 40170,u.. A suitable amount of the maltitol core particles and the fine sugar alcohol particles are placed in a mixer, and are gradually heated with stirring. The ratio of the fine sugar alcohol particles is in the range of 30-100 wt parts, preferably 40-100 wt parts, to 100 wt parts of the maltitol core particles.
In general, the addition of an excess of fine sugar alcohol particles is preferable. The temperature used for the heating is dependent upon the type of low hygroscopic sugar alcohol, and is preferably lower than the softening temperatures of the sugar alcohol. In order to increase the amount of fine sugar alcohol particles coated onto the core particles, a relatively high temperature should be selected. Conversely, to decrease the amount of fine sugar alcohol particles coated onto the core particles, a relatively low temperature should be selected. The temperature is usually 4095 C, preferably 6080C.
The mixture of particles is heated to the predetermined temperature and is continuously stirred at that temperature until the fine sugar alcohol particles are uniformly coated onto the surface of the molten core particles. The time required for the coating is dependent upon the temperature of the mixture of particles. and is usually in the range of 30-120 minutes. The stirring velocity is selected so as to give uniform and suffi cient contact of the fine sugar alcohol particles with the maltitol core particles. When the stirring operation is continued, enough fine sugar alcohol particles are coated onto the surface of the maltitol core particles to decrease tackiness and to improve fluidity. The heating is stopped at this stage, and the mixture is cooled and sifted to separate excess of fine sugar alcohol particles and give the composite maltitol powder. Excess fine sugar alcohol particles can be separated by sifting and can be recycled.
Suitable mixers used in the process of the invention include conventional fixed vessel mixers, rotary vessel mixers, and other mixers used for mixing and blending solid particles. A mixer whose inner temperature can be controlled is preferable. Suitable mixers include rotary cylindrical mixers, jacket cylindrical mixers, and the like.
The low caking composite maltitol powder will not cake when kept in air having a relative humidity of 59% and temperature of 37C for 2 hours. On the other hand, conventional powders containing maltitol will cake within several minutes.
Having generally described the invention, a more complete understanding can be obtained by reference to certain specific examples, which are included for purposes of illustration only and are not intended to be limiting unless otherwise specified.
EXAMPLE 1 A 750 kg portion of an aqueous solution containing 75% solid component composed mainly of maltitol (75% maltitol, 57r sorbitol and 20% of a hydrogenated oligosaccharide higher than a trisaccharide alcohol) was condensed in a vacuum of 740750 mm Hg at a maximum temperature of l l5C, to form a concentrate containing substantially no water. The concentrate was cooled, crushed with a hammer crusher and was sifted in air having a relative humidity of 40%, to obtain -30 mesh particles (SOD-1700a). A 200 kg amount of the resulting core particles containing maltitol and 40 kg of fine sorbitol particles of diameter less than 100p. (passed through a 150 mesh sieve) were placed in a 1000 liter horizontal cylindrical mixer equipped with a jacket, and the mixture was heated to 60C at a stirring rate of 10 rpm. After stirring 60 minutes with heating, the mixture was cooled to obtain 240 kg of a mixture of the composite maltitol powder. The composite powder had an angle of repose of 38, and contained wt parts of sorbitol per 100 wt parts of core particles. Even though the composite powder was kept for more than 2 hours in an atmosphere with relative humidity of 59% at 37C. the fluidity of the composite powder did not decrease, and the composite powder did not cake. On the contrary, when uncoated maltitol particles were exposed to the same atmosphere, the particles immediately caked.
EXAMPLE 2 A 200 kg portion of the maltitol core particles of Example and 100 kg of fine particles of hydrogenated starch syrup solids (passed through a 150 mesh sieve; less than 100p. diameter) were placed in a I000 liter horizontal cylindrical mixer equipped with a jacket. The mixture was heated at 75C with stirring at a rate of 10 rpm. for 60 minutes. and then was cooled and sifted to give 240 kg of the composite maltitol powder.
The composite powder had an angle of repose of 36, and contained 20 wt parts of hydrogenated starch syrup solids per wt parts of core particles. Even though the composite powder was kept for more than 2 hours in an atmosphere with a relative humidity of 59%, at 37C, the fluidity of the composite powder did not decrease, and the composite powder did not cake.
Having now fully described the invention, it will be apparent to one of ordinary skill in the art that many changes and modifications can be made thereto without departing from the spirit or scope of the invention as set forth herein.
What is claimed as new and intended to be covered by letters patent is:
l. A low caking composite maltitol powder which comprises:
core particles containing more than 50% by weight of maltitol and a coating of fine low hygroscopic sugar alcohol particles having a diameter less than onethird of the diameter of the core particles.
2. The low caking composite maltitol powder of claim 1, wherein the low hygroscopic sugar alcohol is selected from the group consisting of sorbitol, mannitol, xylitol and hydrogenated starch syrup solids.
3. The low caking composite maltitol powder of claim 1, wherein the core particles have a diameter of l0O-4000p., and the fine sugar alcohol particles have a diameter of less than onethird that of the core particles, in the range of 20350,u.
4. The low caking composite maltitol powder of claim 1, wherein the weight ratio of fine sugar alcohol particles to core particles is lO-lOO I00.
5. A process for preparing a low caking composite maltitol, which comprises: mixing 100 wt parts of core particles containing more than 50% by weight of maltitol and having a diameter of 100-4000p., with 10-200 wt. parts of fine sugar alcohol particles with a diameter less than one-third that of the core particles, heating the mixture with stirring at a temperature of 4095C to coat the fine sugar alcohol particles onto the surface of the core particles, and cooling the product mixture.
6. The process of claim 5, wherein the sugar alcohol is selected from the group consisting of sorbitol, mannitol, xylitol and hydrogenated starch syrup solids.
7. The process of claim 5, wherein excess fine sugar alcohol particles, which are not bonded onto the surface of the core particles, are separated from the product mixture.
8. The process of claim 5 which further comprises:
concentrating and cooling an aqueous solution containing maltitol to form a solid block;
crushing said block and sifting the resulting particles having a diameter of l004000/.L;
mixing sugar alcohol particles with said crushed and sifted particles having a diameter less than onethird that of said crushed and sifted particles with stirring at a temperature of 4095C to form a product mixture;
cooling the product mixture; and
separating excess sugar alcohol particles from said UNITED STATES PATENT AND TRADEMARK OFFICE CERTIFICATE OF CORRECTION PATENT N0. 1 3,915,736 DATED November 28, 1975 lN\/ ENTOR(S) Koichi Oyamada, Seiji Hashimoto, Kazuaki Kuno, and
Ya subumi Hirabaya shi l It IS certified that error appears m the above-ldentrfled patent and that sad Letters Patent are hereby corrected as shown below:
Change Assignee from "Nikken Checicals 00., Ltd." to
--Nikken Chemicals 00., Ltd.-.
Signed and Scaled tlais sixteenth Day of March 1976 [SEAL] A ttes t:
RUTH. C. MASON C. MARSHALL DANN ANPSIHIZ ffm (nmmixsiuner ufParenrs and Trademarks

Claims (8)

1. A LOW CAKING COMPOSITE MALTITOL POWDER WHICH COMPRISES: CORE PARTICLES CONTAINING MORE THAN 50% BY WEIGHT MALTITOL AND A COATING OF FINE LOW HYGROSCOPIC SUGAR ALCOHOL PARTICLES HAVING A DIAMETER LESS THAN ONE-THIRD OF THE DIAMETER OF THE CORE PARTICLES.
2. The low caking composite maltitol powder of claim 1, wherein the low hygroscopic sugar alcohol is selected from the group consisting of sorbitol, mannitol, xylitol and hydrogenated starch syrup solids.
3. The low caking composite maltitol powder of claim 1, wherein the core particles have a diameter of 100-4000 Mu , and the fine sugar alcohol particles have a diameter of less than one-third that of the core particles, in the range of 20-350 Mu .
4. The low caking composite maltitol powder of claim 1, wherein the weight ratio of fine sugar alcohol particles to core particles is 10-100 : 100.
5. A process for preparing a low caking composite maltitol, which comprises: mixing 100 wt parts of core particles containing more than 50% by weight of maltitol and having a diameter of 100-4000 Mu , with 10-200 wt. parts of fine sugar alcohol particles with a diameter less than one-third that of the core particles, heating the mixture with stirring at a temperature of 40*-95*C to coat the fine sugar alcohol particles onto the surface of the core particles, and cooling the product mixture.
6. The process of claim 5, wherein the sugar alcohol is selected from the group consisting of sorbitol, mannitol, xylitol and hydrogenated starch syrup solids.
7. The process of claim 5, wherein excess fine sugar alcohol particles, which are not bonded onto the surface of the core particles, are separated from the product mixture.
8. The process of claim 5 which further comprises: concentrating and cooling an aqueous solution containing maltitol to form a solid block; crushing said block and sifting the resulting particles having a diameter of 100-4000 Mu ; mixing sugar alcohol particles with said crushed and sifted particles having a diameter less than one-third that of said crushed and sifted particles with stirring at a temperature of 40*-95*C to form a product mixture; cooling the product mixture; and separating excess sugar alcohol particles from said product mixture.
US485237A 1973-07-07 1974-07-02 Composite maltitol powder Expired - Lifetime US3915736A (en)

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IT (1) IT1015695B (en)

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US4248895A (en) * 1978-12-21 1981-02-03 Life Savers, Inc. Dehydrated higher polyalcohols, comestibles and chewing gum containing same and method
US4408041A (en) * 1981-02-12 1983-10-04 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Anhydrous crystals of maltitol and the whole crystalline hydrogenated starch hydrolysate mixture solid containing the crystals, and process for the production and uses thereof
US4789559A (en) * 1981-02-12 1988-12-06 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Anhydrous crystals of maltitol and the whole crystalline hydrogenated starch hydrolysate mixture solid containing the crystals, and process for the production and uses thereof
US4831129A (en) * 1985-10-02 1989-05-16 Roquette Freres Directly compressible powdered maltitol and its process of preparation
US4931294A (en) * 1988-03-21 1990-06-05 Wm. Wrigley Jr. Company Environmentally stable chewing gum composition containing xylitol
US4933188A (en) * 1987-12-31 1990-06-12 Warner-Lambert Company Chewing gum compositions with improved physical stability
US4959225A (en) * 1988-10-28 1990-09-25 Warner-Lambert Company Synergistic sweetening compositions containing chlorodeoxysugars and maltitol and methods for preparing same
US4976972A (en) * 1988-02-24 1990-12-11 Wm. Wrigley Jr. Company Chewing gum with improved sweetness employing xylitol rolling compound
US5017400A (en) * 1988-06-10 1991-05-21 Suomen Xyrofin Oy Non-cariogenic sweetener
US5427800A (en) * 1991-10-24 1995-06-27 Etablissements Rinrone Process for preparation of an extract of active ingredients in a dry adsorbable form and adsorbable form and adsorbable microgranules thus obtained
US5547689A (en) * 1994-02-01 1996-08-20 Roquette Freres Chewing-gum composition of improved organoleptic quality and process enabling such a chewing-gum to be prepared
US5637334A (en) * 1993-09-30 1997-06-10 Wm. Wrigley Jr. Company Chewing gum containing maltitol
US5651829A (en) * 1995-03-29 1997-07-29 Roquette Freres Maltitol composition and process for preparing it
US6344591B2 (en) 1997-09-26 2002-02-05 Roquette Freres Maltitol crystals of particular forms, crystalline compositions containing them and processes for their preparation
US6743456B1 (en) * 1998-05-07 2004-06-01 Roquette Freres Sweetening composition and its uses
WO2007142896A3 (en) * 2006-05-31 2008-01-31 Oms Investments Inc Composition and method for inhibiting caking in a urea containing fertilzer
US20090163700A1 (en) * 2007-12-20 2009-06-25 Roquette Freres Granulated maltitol for direct compression and method of preparation thereof
US8709527B2 (en) 2006-10-17 2014-04-29 Roquette Freres Granulated sweetening composition
US11091404B2 (en) 2018-04-25 2021-08-17 Oms Investments, Inc. Fertilizer compositions having slow-release nitrogen compounds and methods of forming thereof
CN116270522A (en) * 2023-04-27 2023-06-23 北京华靳制药有限公司 Fructose diphosphate sodium capsule and preparation method thereof

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US4381318A (en) * 1981-01-05 1983-04-26 Ici Americas Inc. Maltitol containing gel base systems
JPS6158540A (en) * 1984-08-29 1986-03-25 Ajinomoto Co Inc Low-calorific candy
DE3729831A1 (en) * 1987-09-05 1989-03-23 Merck Patent Gmbh SUGAR-FREE BINDERS
US4772411A (en) * 1988-01-28 1988-09-20 International Flavors & Fragrances Inc. Ethyl norbornyl alkyl ethers, organoleptic uses thereof and process for preparing same

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Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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US4408041A (en) * 1981-02-12 1983-10-04 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Anhydrous crystals of maltitol and the whole crystalline hydrogenated starch hydrolysate mixture solid containing the crystals, and process for the production and uses thereof
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Also Published As

Publication number Publication date
FR2236005B1 (en) 1978-11-24
FR2236005A1 (en) 1975-01-31
IT1015695B (en) 1977-05-20
JPS5025514A (en) 1975-03-18
DE2432562A1 (en) 1975-01-23
GB1419360A (en) 1975-12-31

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